Printed in the Republic of Korea http://dx.doi.org/10.5012/jkcs.2016.60.2.1
SUPPORTING INFORMATION
Synthesis and Crystal Structures of Zn(II)- and Cd(II) - Isonicotinate Complexes
Bon Kweon Koo
Department of Life Chemistry, Catholic University of Daegu, Gyeongbuk 38430, Korea.
E-mail: [email protected]
(Received December 31, 2015; Accepted January 26, 2016)
data_S4911
_audit_creation_method SHELXTL-97 _chemical_name_systematic
;
?
;
_chemical_name_common ? _chemical_melting_point ?
_chemical_formula_moiety 'C12 H16 N2 O8 Zn' _chemical_formula_sum
'C12 H16 N2 O8 Zn'
_chemical_formula_weight 381.64
loop_
_atom_type_symbol _atom_type_description
_atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' 0.2839 1.4301
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z' '-x, -y, -z'
_cell_length_a 6.3286(4) _cell_length_b 6.8862(4) _cell_length_c 9.2840(5) _cell_angle_alpha 96.098(2) _cell_angle_beta 105.005(2) _cell_angle_gamma 112.995(2) _cell_volume 349.83(4) _cell_formula_units_Z 1
_cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6238 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 26.02
_exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.812
_exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196
_exptl_absorpt_coefficient_mu 1.803 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7033 _exptl_absorpt_correction_T_max 0.8995 _exptl_absorpt_process_details 'Bruker SADABS'
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 223(2)
_diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14592
_diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.40 _reflns_number_total 1749 _reflns_number_gt 1608
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, con- ventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma (F2) is used only for calculating R-factors (gt) etc. and is not relevant to the choice of reflections for refinement. R-fac- tors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full
_refine_ls_weighting_scheme calc _refine_ls_weighting_details
'calc w=1/[\s2(Fo2)+(0.0236P)2+0.1321P] where P=(Fo2+2Fc2)/3' _atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1749 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0245 _refine_ls_wR_factor_ref 0.0567 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000
loop_
_atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z
_atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy
_atom_site_symmetry_multiplicity _atom_site_calc_flag
_atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group
Zn1 Zn 0.0000 0.0000 0.0000 0.01670(9) Uani 1 2 d S ..
O1W O -0.2244(2) -0.2612(2) 0.08058(15) 0.0235(3) Uani 1 1 d . . . H1W1 H -0.332(5) -0.270(4) 0.114(3) 0.042(7) Uiso 1 1 d . . . H2W1 H -0.158(5) -0.322(4) 0.125(3) 0.038(7) Uiso 1 1 d . . . O2W O 0.1732(2) -0.1939(2) -0.04244(14) 0.0194(2) Uani 1 1 d . . . H1W2 H 0.093(4) -0.305(4) -0.107(3) 0.040(7) Uiso 1 1 d . . . H2W2 H 0.237(5) -0.225(4) 0.025(3) 0.040(7) Uiso 1 1 d . . . N1 N 0.2437(2) 0.1395(2) 0.22986(14) 0.0167(3) Uani 1 1 d . . . C1 C 0.1511(3) 0.1421(3) 0.34451(18) 0.0177(3) Uani 1 1 d . . . H1A H -0.0170 0.0987 0.3196 0.021 Uiso 1 1 calc R . . C2 C 0.2919(3) 0.2058(3) 0.49729(17) 0.0174(3) Uani 1 1 d . . . H2A H 0.2200 0.2048 0.5742 0.021 Uiso 1 1 calc R . . C3 C 0.5407(3) 0.2715(2) 0.53624(17) 0.0153(3) Uani 1 1 d . . . C4 C 0.6387(3) 0.2777(3) 0.41824(18) 0.0188(3) Uani 1 1 d . . .
H4 H 0.8072 0.3273 0.4402 0.023 Uiso 1 1 calc R . . C5 C 0.4851(3) 0.2099(3) 0.26762(18) 0.0196(3) Uani 1 1 d . . . H5 H 0.5530 0.2135 0.1885 0.023 Uiso 1 1 calc R . . C6 C 0.6986(3) 0.3302(3) 0.70239(17) 0.0177(3) Uani 1 1 d . . . O3 O 0.5892(2) 0.2799(2) 0.79770(13) 0.0256(3) Uani 1 1 d . . . O4 O 0.9249(2) 0.4195(2) 0.73242(13) 0.0247(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12
Zn1 0.01570(14) 0.02252(15) 0.01136(13) 0.00257(10) 0.00325(10) 0.00891(11)
O1W 0.0202(6) 0.0284(7) 0.0261(6) 0.0121(5) 0.0112(5) 0.0111(6) O2W 0.0202(6) 0.0244(6) 0.0131(5) 0.0018(5) 0.0014(5) 0.0124(5) N1 0.0177(6) 0.0198(7) 0.0137(6) 0.0043(5) 0.0058(5) 0.0087(5) C1 0.0150(7) 0.0207(8) 0.0174(7) 0.0047(6) 0.0050(6) 0.0079(6) C2 0.0190(8) 0.0200(8) 0.0149(7) 0.0060(6) 0.0078(6) 0.0082(6) C3 0.0181(7) 0.0123(7) 0.0144(7) 0.0032(6) 0.0037(6) 0.0066(6) C4 0.0141(7) 0.0206(8) 0.0191(7) 0.0025(6) 0.0044(6) 0.0063(6) C5 0.0184(8) 0.0243(8) 0.0167(7) 0.0040(6) 0.0086(6) 0.0084(7) C6 0.0210(8) 0.0166(7) 0.0159(7) 0.0025(6) 0.0034(6) 0.0107(6) O3 0.0263(6) 0.0401(7) 0.0154(5) 0.0089(5) 0.0075(5) 0.0186(6) O4 0.0183(6) 0.0299(7) 0.0202(6) 0.0039(5) 0.0012(5) 0.0085(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix.
The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approx- imate (isotropic) treatment of cell esds is used for esti- mating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance
_geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2W 2.0963(12) . ? Zn1 O2W 2.0963(12) 2 ?
Zn1 N1 2.1350(13) . ? Zn1 N1 2.1350(13) 2 ? Zn1 O1W 2.1570(13) . ? Zn1 O1W 2.1570(13) 2 ? O1W H1W1 0.80(3) . ? O1W H2W1 0.78(3) . ? O2W H1W2 0.80(3) . ? O2W H2W2 0.75(3) . ? N1 C5 1.342(2) . ? N1 C1 1.343(2) . ? C1 C2 1.381(2) . ? C1 H1A 0.9400 . ? C2 C3 1.389(2) . ? C2 H2A 0.9400 . ? C3 C4 1.389(2) . ? C3 C6 1.515(2) . ? C4 C5 1.386(2) . ? C4 H4 0.9400 . ? C5 H5 0.9400 . ? C6 O4 1.255(2) . ? C6 O3 1.256(2) . ?
loop_
_geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle
_geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2W Zn1 O2W 180.00(8) . 2 ? O2W Zn1 N1 91.86(5) . . ? O2W Zn1 N1 88.14(5) 2 . ? O2W Zn1 N1 88.14(5) . 2 ? O2W Zn1 N1 91.86(5) 2 2 ? N1 Zn1 N1 180.00(5) . 2 ? O2W Zn1 O1W 86.78(5) . . ? O2W Zn1 O1W 93.22(5) 2 . ? N1 Zn1 O1W 88.61(5) . . ? N1 Zn1 O1W 91.39(5) 2 . ? O2W Zn1 O1W 93.22(5) . 2 ? O2W Zn1 O1W 86.78(5) 2 2 ? N1 Zn1 O1W 91.39(5) . 2 ? N1 Zn1 O1W 88.61(5) 2 2 ? O1W Zn1 O1W 180.00(7) . 2 ? Zn1 O1W H1W1 129.9(17) . . ? Zn1 O1W H2W1 115.0(18) . . ? H1W1 O1W H2W1 106(2) . . ? Zn1 O2W H1W2 117.1(17) . . ?
Zn1 O2W H2W2 117.3(19) . . ? H1W2 O2W H2W2 105(2) . . ? C5 N1 C1 117.66(13) . . ? C5 N1 Zn1 123.36(10) . . ? C1 N1 Zn1 118.76(10) . . ? N1 C1 C2 122.89(15) . . ? N1 C1 H1A 118.6 . . ? C2 C1 H1A 118.6 . . ? C1 C2 C3 119.37(15) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 117.94(14) . . ? C4 C3 C6 121.24(14) . . ? C2 C3 C6 120.81(14) . . ? C5 C4 C3 119.21(15) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.83(15) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? O4 C6 O3 125.87(15) . . ? O4 C6 C3 117.82(14) . . ? O3 C6 C3 116.30(14) . . ?
loop_
_geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion
_geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag
O2W Zn1 N1 C5 45.18(13) . . . . ? O2W Zn1 N1 C5 -134.82(13) 2 . . . ? O1W Zn1 N1 C5 131.92(13) . . . . ? O1W Zn1 N1 C5 -48.08(13) 2 . . . ?
O2W Zn1 N1 C1 -129.38(12) . . . . ? O2W Zn1 N1 C1 50.62(12) 2 . . . ? O1W Zn1 N1 C1 -42.64(12) . . . . ? O1W Zn1 N1 C1 137.36(12) 2 . . . ? C5 N1 C1 C2 -2.5(2) . . . . ?
Zn1 N1 C1 C2 172.39(12) . . . . ? N1 C1 C2 C3 0.3(2) . . . . ? C1 C2 C3 C4 2.4(2) . . . . ? C1 C2 C3 C6 -176.48(14) . . . . ? C2 C3 C4 C5 -2.8(2) . . . . ? C6 C3 C4 C5 176.07(14) . . . . ? C1 N1 C5 C4 2.0(2) . . . . ? Zn1 N1 C5 C4 -172.58(12) . . . . ? C3 C4 C5 N1 0.6(3) . . . . ? C4 C3 C6 O4 11.9(2) . . . . ? C2 C3 C6 O4 -169.30(14) . . . . ? C4 C3 C6 O3 -166.65(15) . . . . ? C2 C3 C6 O3 12.2(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A
O2W H2W2 O3 0.75(3) 1.89(3) 2.6435(17) 176(3) 2_656 O2W H1W2 O4 0.80(3) 1.99(3) 2.7883(17) 174(2) 1_444 O1W H1W1 O3 0.80(3) 1.99(3) 2.7878(18) 177(3) 2_556 O1W H2W1 O4 0.78(3) 2.08(3) 2.8472(18) 168(2) 2_656
_diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.40
_diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.416
_refine_diff_density_min -0.325 _refine_diff_density_rms 0.071
data_KA39
_audit_creation_method SHELXTL _chemical_name_systematic
; ?
;
_chemical_name_common ? _chemical_melting_point ?
_chemical_formula_moiety 'C12 H16 Cd N2 O8' _chemical_formula_sum
'C12 H16 Cd N2 O8'
_chemical_formula_weight 428.67
loop_
_atom_type_symbol _atom_type_description
_atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cd' 'Cd' -0.8075 1.2024
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz 'x, y, z'
'-x, -y, -z'
_cell_length_a 6.4300(3) _cell_length_b 6.9164(4) _cell_length_c 9.4100(5) _cell_angle_alpha 94.662(2) _cell_angle_beta 104.7583(19) _cell_angle_gamma 111.9290(19) _cell_volume 368.07(3)
_cell_formula_units_Z 1
_cell_measurement_temperature 223(2)
_cell_measurement_reflns_used 8594 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.33
_exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.934
_exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 214
_exptl_absorpt_coefficient_mu 1.529 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7811 _exptl_absorpt_correction_T_max 0.9139 _exptl_absorpt_process_details 'Bruker SADABS'
_exptl_special_details
; ?
;
_diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'PHOTON 100 CMOS' _diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13957
_diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 28.38 _reflns_number_total 1836 _reflns_number_gt 1794
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, con- ventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma (F2) is used only for calculating R-factors (gt) etc. and is not relevant to the choice of reflections for refinement. R-fac- tors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full
_refine_ls_weighting_scheme calc _refine_ls_weighting_details
'calc w=1/[\s2(Fo2)+(0.0120P)2+0.2395P] where P=(Fo2+2Fc2)/3' _atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1836 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0218 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0421 _refine_ls_wR_factor_gt 0.0412 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000
loop_
_atom_site_label _atom_site_type_symbol
_atom_site_fract_x _atom_site_fract_y _atom_site_fract_z
_atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy
_atom_site_symmetry_multiplicity _atom_site_calc_flag
_atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group
Cd1 Cd 0.0000 0.0000 0.0000 0.01994(6) Uani 1 2 d S . . O1 O 0.1705(3) -0.2249(2) -0.04792(16) 0.0236(3) Uani 1 1 d . . . H1W2 H 0.161(5) 0.320(4) -0.151(3) 0.036(7) Uiso 1 1 d . . . H2W1 H 0.228(5) -0.260(4) 0.024(3) 0.042(8) Uiso 1 1 d . . . O2 O 0.2265(3) 0.2636(3) -0.10343(18) 0.0311(3) Uani 1 1 d . . . H1W1 H 0.086(4) -0.330(4) -0.108(3) 0.036(7) Uiso 1 1 d . . . H2W2 H 0.334(5) 0.275(4) -0.134(3) 0.041(8) Uiso 1 1 d . . . N1 N 0.2589(3) 0.1394(2) 0.24026(16) 0.0201(3) Uani 1 1 d . . . C1 C 0.4933(3) 0.2072(3) 0.2731(2) 0.0235(4) Uani 1 1 d . . . H1 H 0.5579 0.2076 0.1940 0.028 Uiso 1 1 calc R . . C2 C 0.6439(3) 0.2766(3) 0.4186(2) 0.0215(4) Uani 1 1 d . . . H2 H 0.8076 0.3247 0.4373 0.026 Uiso 1 1 calc R . . C3 C 0.5513(3) 0.2745(3) 0.53641(18) 0.0168(3) Uani 1 1 d . . . C4 C 0.3091(3) 0.2087(3) 0.50285(19) 0.0198(4) Uani 1 1 d . . . H4 H 0.2402 0.2082 0.5798 0.024 Uiso 1 1 calc R . . C5 C 0.1714(3) 0.1440(3) 0.3545(2) 0.0211(4) Uani 1 1 d . . . H5 H 0.0078 0.1009 0.3327 0.025 Uiso 1 1 calc R . . C6 C 0.7086(3) 0.3405(3) 0.69799(19) 0.0198(4) Uani 1 1 d . . . O3 O 0.9273(2) 0.4216(2) 0.72038(15) 0.0268(3) Uani 1 1 d . . . O4 O 0.6086(2) 0.3072(2) 0.79699(14) 0.0295(3) Uani 1 1 d . . .
loop_
_atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12
Cd1 0.01914(10) 0.02675(11) 0.01250(9) 0.00182(7) 0.00265(7) 0.00973(8)
O1 0.0244(7) 0.0294(8) 0.0165(6) 0.0017(6) 0.0019(6) 0.0140(6) O2 0.0238(8) 0.0392(9) 0.0376(8) 0.0184(7) 0.0141(7) 0.0155(7) N1 0.0199(7) 0.0232(8) 0.0153(7) 0.0027(6) 0.0039(6) 0.0081(6) C1 0.0213(9) 0.0303(10) 0.0179(8) 0.0028(7) 0.0084(7) 0.0082(8) C2 0.0162(8) 0.0247(9) 0.0211(9) 0.0024(7) 0.0044(7) 0.0070(7) C3 0.0193(8) 0.0146(8) 0.0156(8) 0.0027(6) 0.0030(6) 0.0076(7) C4 0.0205(9) 0.0229(9) 0.0163(8) 0.0040(7) 0.0069(7) 0.0084(7)
C5 0.0173(8) 0.0255(9) 0.0186(8) 0.0029(7) 0.0044(7) 0.0078(7) C6 0.0217(9) 0.0201(9) 0.0176(8) 0.0023(7) 0.0025(7) 0.0111(7) O3 0.0186(6) 0.0335(7) 0.0215(7) 0.0026(6) 0.0003(5) 0.0078(6) O4 0.0267(7) 0.0484(9) 0.0162(6) 0.0068(6) 0.0053(5) 0.0193(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix.
The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance
_geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 O1 2.2880(14) . ? Cd1 O1 2.2880(14) 2 ? Cd1 N1 2.3112(14) 2 ? Cd1 N1 2.3112(14) . ? Cd1 O2 2.3281(15) . ? Cd1 O2 2.3281(15) 2 ? O1 H2W1 0.79(3) . ? O1 H1W1 0.79(3) . ? O2 H1W2 0.77(3) . ? O2 H2W2 0.79(3) . ? N1 C5 1.338(2) . ? N1 C1 1.341(2) . ? C1 C2 1.383(3) . ? C1 H1 0.9400 . ? C2 C3 1.384(2) . ? C2 H2 0.9400 . ? C3 C4 1.389(2) . ? C3 C6 1.517(2) . ? C4 C5 1.380(2) . ? C4 H4 0.9400 . ? C5 H5 0.9400 . ? C6 O4 1.251(2) . ? C6 O3 1.255(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle
_geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cd1 O1 180.00(7) . 2 ? O1 Cd1 N1 87.39(5) . 2 ? O1 Cd1 N1 92.61(5) 2 2 ? O1 Cd1 N1 92.61(5) . . ? O1 Cd1 N1 87.39(5) 2 . ? N1 Cd1 N1 180.00(8) 2 . ? O1 Cd1 O2 93.42(6) . . ? O1 Cd1 O2 86.58(6) 2 . ? N1 Cd1 O2 86.16(5) 2 . ? N1 Cd1 O2 93.84(5) . . ? O1 Cd1 O2 86.58(6) . 2 ? O1 Cd1 O2 93.42(6) 2 2 ? N1 Cd1 O2 93.84(5) 2 2 ? N1 Cd1 O2 86.16(5) . 2 ? O2 Cd1 O2 180.00(8) . 2 ? Cd1 O1 H2W1 113.9(19) . . ? Cd1 O1 H1W1 115.0(18) . . ? H2W1 O1 H1W1 107(3) . . ? Cd1 O2 H1W2 115.3(19) . . ? Cd1 O2 H2W2 132.2(19) . . ? H1W2 O2 H2W2 106(3) . . ? C5 N1 C1 117.58(15) . . ? C5 N1 Cd1 118.72(11) . . ? C1 N1 Cd1 123.62(12) . . ? N1 C1 C2 122.68(17) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.37(16) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.14(16) . . ? C2 C3 C6 121.24(15) . . ? C4 C3 C6 120.62(16) . . ? C5 C4 C3 118.85(17) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 123.33(16) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? O4 C6 O3 125.84(16) . . ? O4 C6 C3 116.95(16) . . ? O3 C6 C3 117.21(16) . . ?
loop_
_geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion
_geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag
O1 Cd1 N1 C5 -128.01(13) . . . . ? O1 Cd1 N1 C5 51.99(13) 2 . . . ? O2 Cd1 N1 C5 138.39(14) . . . . ? O2 Cd1 N1 C5 -41.61(14) 2 . . . ? O1 Cd1 N1 C1 48.62(15) . . . . ? O1 Cd1 N1 C1 -131.38(15) 2 . . . ? O2 Cd1 N1 C1 -44.98(15) . . . . ? O2 Cd1 N1 C1 135.02(15) 2 . . . ? C5 N1 C1 C2 1.2(3) . . . . ? Cd1 N1 C1 C2 -175.45(14) . . . . ? N1 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 -2.1(3) . . . . ? C1 C2 C3 C6 177.46(16) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C6 C3 C4 C5 -178.11(16) . . . . ? C1 N1 C5 C4 -1.9(3) . . . . ? Cd1 N1 C5 C4 174.93(14) . . . . ?
C3 C4 C5 N1 0.6(3) . . . . ? C2 C3 C6 O4 -170.74(17) . . . . ? C4 C3 C6 O4 8.8(2) . . . . ? C2 C3 C6 O3 8.6(3) . . . . ? C4 C3 C6 O3 -171.86(16) . . . . ?
loop_
_geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A
O1 H1W1 O3 0.79(3) 2.00(3) 2.778(2) 168(3) 1_444 O1 H2W1 O4 0.79(3) 1.87(3) 2.6518(19) 173(3) 2_656 O2 H1W2 O3 0.77(3) 2.05(3) 2.808(2) 169(3) 1_454 O2 H2W2 O4 0.79(3) 1.98(3) 2.769(2) 178(3) 1_554
_diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.38
_diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.435
_refine_diff_density_min -0.331 _refine_diff_density_rms 0.090
