SUPPORTING INFORMATIONDual Purpose Br-Containing Schiff Base Cu(II) Complexes for DSSC Dyes and Polymer Flame Retardants

(1)

Printed in the Republic of Korea

https://doi.org/10.5012/jkcs.2017.61.3.1

Notes

SUPPORTING INFORMATION

Dual Purpose Br-Containing Schiff Base Cu(II) Complexes for DSSC Dyes and Polymer Flame Retardants

Keita Takahashi^†, Shinnosuke Tanaka^†, Marin Yamaguchi^†, Yuki Tunoda^†, Takashiro Akitsu^†,*, Mutsumi Sugiyama^‡, Rakesh Kumar Soni^§, and Dohyun Moon^#,*

†Department of Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan. ^*E-mail: [email protected]

‡Department of Electrical Engineering, Faculty of Science and Technology, Tokyo University of Science, Chiba, Japan.

§Department of Chemistry, Chaudhary Charan Singh University, Meerut, UP, India.

#Beamline Department, Pohang Accelerator Laboratory, Korea. ^*E-mail: [email protected] (Received March 14, 2017; Accepted April 11, 2017)

#=======================================

data_global

#=======================================

_audit_creation_date '2016-12-09'

_audit_creation_method 'PDXL Version 2.6.1.2 (Rigaku, 2015)' loop_

_audit_conform_dict_name _audit_conform_dict_version _audit_conform_dict_location

cif_core.dic 2.4.2 ftp://ftp.iucr.org/pub/cif_core.dic cif_pd.dic 1.0.1 ftp://ftp.iucr.org/pub/cif_pd.dic

#=======================================

# PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ?

_journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ?

#=======================================

# SUBMISSION DETAILS

_publ_contact_author_name 'ENTER NAME' _publ_contact_author_address

;

ENTER ADDRESS

;

_publ_contact_author_fax 'ENTER FAX NUMBER' _publ_contact_author_email 'ENTER EMAIL ADDRESS' _publ_contact_author_phone 'ENTER PHONE NUMBER' _publ_contact_letter

;

ENTER TEXT OF LETTER

;

_publ_requested_journal 'ENTER JOURNAL NAME HERE' _publ_requested_category ? # CHOOSE FA FI FO FM EI EO EM AD or SC

_publ_requested_coeditor_name ?

#=======================================

# TITLE AND AUTHOR LIST _publ_section_title

;

ENTER SECTION TITLE

;

_publ_section_title_footnote

;

ENTER FOOTNOTE TO TITLE OF PAPER

; loop_

_publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME '

;

FIRST AUTHORS FOOTNOTES

;

FIRST AUTHORS ADDRESS

;

#=======================================

# TEXT

_publ_section_synopsis

;

ENTER SYNOPSIS

;

_publ_section_abstract

;

ENTER ABSTRACT

;

_publ_section_comment

;

(2)

ENTER TEXT

;

_publ_section_acknowledgements

;

ENTER ACKNOWLEDGEMENTS

;

_publ_section_references

;

ENTER OTHER REFERENCES

PDXL Version 2.6.1.2 (2015).

Integrated X-ray Powder Diffraction Software.

Rigaku Corporation, Tokyo 196-8666, Japan.

;

_publ_section_figure_captions

;

ENTER FIGURE CAPTIONS

;

_publ_section_exptl_prep

;

ENTER COMPOUND PREPARATION DETAILS

;

_publ_section_exptl_refinement

;

ENTER SPECIAL DETAILS OF THE REFINEMENT

;

#=======================================

data_Indexing#1

#=======================================

# CHEMICAL DATA _chemical_name_systematic

; ?

;

_chemical_name_common 'Indexing#1'

_chemical_formula_structural 'C26 H16 Br2 Cu N2 O6' _chemical_formula_analytical ?

_chemical_formula_moiety ?

_chemical_formula_sum 'Br2 C27 Cu1 H20 N2 O7' _chemical_formula_weight 707.811

_chemical_melting_point ? _chemical_compound_source ?

#=======================================

# CRYSTAL DATA

_space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall ?

loop_

_symmetry_equiv_pos_site_id

_symmetry_equiv_pos_as_xyz 1 'x,y,z'

2 '-x,1/2+y,-z'

_cell_length_a 11.851(4) _cell_length_b 7.8368(14) _cell_length_c 22.026(6) _cell_angle_alpha 90 _cell_angle_beta 99.34(2) _cell_angle_gamma 90 _cell_volume 2018.6(9) _cell_formula_units_Z 2

_cell_measurement_temperature 298 _rigaku_reference_intensity_ratio 22.21 _pd_char_colour 'colourless'

_exptl_crystal_density_diffrn 1.16 _exptl_crystal_F_000 702.00

#=======================================

# EXPERIMENTAL DATA

_computing_data_collection 'ENTER THE DATA COL- LECTION PROGRAM NAME'

_diffrn_measurement_device_type 'ENTER THE MEA- SUREMENT DEVICE NAME'

_diffrn_radiation_type 'Cu K\a'

_diffrn_radiation_wavelength 1.541861 _diffrn_measurement_method 2\q _diffrn_ambient_temperature 298 _pd_meas_2theta_range_min 2.9484 _pd_meas_2theta_range_max 54.9656 _pd_meas_2theta_range_inc 0.0137 _pd_meas_number_of_points 3803 _reflns_number_total 528

_reflns_limit_h_min 0 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 4 _reflns_limit_l_min -13 _reflns_limit_l_max 13

_reflns_d_resolution_high 1.6698 _reflns_d_resolution_low 21.7345

#=======================================

# REFINEMENT DATA

_computing_cell_refinement 'PDXL Version 2.6.1.2 (Rigaku, 2015)'

_computing_structure_solution 'PDXL Version 2.6.1.2 (Rigaku, 2015)'

_computing_structure_refinement 'PDXL Version 2.6.1.2 (Rigaku, 2015)'

_computing_publication_material 'PDXL Version 2.6.1.2

(3)

(Rigaku, 2015)'

_computing_molecular_graphics '?' _refine_special_details

;

_pd_calc_method 'Rietveld Refinement' _refine_ls_weighting_scheme sigma _refine_ls_structure_factor_coef Fsqd

_refine_ls_hydrogen_treatment ? # CHOOSE reffAll refxyz refU noref constr mixed or undef

_refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_number_parameters 19 _refine_ls_matrix_type full _pd_proc_ls_prof_R_factor 0.0636 _pd_proc_ls_prof_wR_expected 0.0164 _pd_proc_ls_prof_wR_factor 0.1236 _refine_ls_goodness_of_fit_all 7.5608 _refine_ls_shift/su_max 0.0110

loop_

_atom_type_symbol _atom_type_description

_atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source

'Br' 'Br' -0.767 1.283

17.1789 5.23580 5.63770 3.98510

2.17230 16.5796 0.260900 41.4328 2.95570

;

International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999),

and KEK Report 88-14, 1-136.

;

'C' 'C' 0.017 0.009

2.31000 1.02000 1.58860 0.865000

20.8439 10.2075 0.568700 51.6512 0.215600

;

'Cu' 'Cu' -2.016 0.590

13.3380 7.16760 5.61580 1.67350

3.58280 0.247000 11.3966 64.8126 1.19100

;

'H' 'H' 0.000 0.000

0.489918 0.262003 0.196767 0.049879 20.6593 7.74039 49.5519 2.20159 0.001305

;

International Tables for Crystallography Vol. C, Table 6.1.1.4 (1999).

;

'N' 'N' 0.029 0.018

12.2126 3.13220 2.01250 1.16630

0.005700 9.89330 28.9975 0.582600 -11.529

;

'O' 'O' 0.046 0.032

3.04850 2.28680 1.54630 0.867000

13.2771 5.70110 0.323900 32.9089 0.250800

;

#=======================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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

Br1 Br -0.394478 0.708559 -0.032820 0 Uiso 1 Br2 Br 0.186444 -0.468159 0.014720 0 Uiso 1 Cu1 Cu 0.000215 0.233839 0.168829 0 Uiso 1 O1 O 0.123181 0.420890 0.135652 0 Uiso 1

(4)

O2 O -0.116376 0.320136 0.104733 0 Uiso 1 O3 O 0.029774 0.047613 0.115704 0 Uiso 1 O4 O -0.099004 0.061627 0.339191 0 Uiso 1 O5 O 0.169847 0.554205 0.244906 0 Uiso 1 O6 O -0.155936 0.028926 0.227280 0 Uiso 1 O7 O 0.231267 0.444821 0.343604 0 Uiso 1 N1 N 0.103493 0.132468 0.239570 0 Uiso 1 N2 N -0.037192 0.406162 0.227992 0 Uiso 1 C1 C -0.207829 0.532498 0.166298 0 Uiso 1 C2 C -0.303096 0.655727 0.163527 0 Uiso 1 C3 C -0.350051 0.737594 0.105118 0 Uiso 1 C4 C -0.322866 0.653342 0.048639 0 Uiso 1 C5 C -0.422463 0.886048 0.106801 0 Uiso 1 C6 C -0.460071 0.933234 0.161748 0 Uiso 1 C7 C -0.431690 0.834334 0.215400 0 Uiso 1 C8 C -0.251280 0.514227 0.052090 0 Uiso 1 C9 C -0.354540 0.698401 0.216988 0 Uiso 1 C10 C 0.112697 -0.067072 0.128100 0 Uiso 1 C11 C 0.191596 -0.091045 0.185573 0 Uiso 1 C12 C 0.281635 -0.351762 0.143055 0 Uiso 1 C13 C 0.196013 -0.328675 0.086256 0 Uiso 1 C14 C 0.364201 -0.489162 0.155394 0 Uiso 1 C15 C 0.452054 -0.480813 0.206547 0 Uiso 1 C16 C 0.464535 -0.337581 0.245705 0 Uiso 1 C17 C 0.382642 -0.207414 0.237713 0 Uiso 1 C18 C 0.284287 -0.217291 0.189279 0 Uiso 1 C19 C 0.165675 -0.011930 0.240619 0 Uiso 1 C20 C -0.129822 0.508486 0.222536 0 Uiso 1 C21 C 0.046913 0.174458 0.294269 0 Uiso 1 C22 C -0.074722 0.088522 0.279310 0 Uiso 1 C23 C 0.029920 0.375128 0.290783 0 Uiso 1 C24 C 0.153302 0.457398 0.298519 0 Uiso 1 C25 C 0.121599 -0.192418 0.079564 0 Uiso 1 C26 C -0.186747 0.448840 0.109933 0 Uiso 1 C27 C 0.214828 0.355581 0.111384 0 Uiso 1 H1 H 0.281225 0.466593 0.105477 0 Uiso 1 H2 H -0.447890 0.972761 0.069570 0 Uiso 1 H3 H 0.253089 0.593801 0.256310 0 Uiso 1 H4 H 0.198581 0.287104 0.070890 0 Uiso 1 H5 H -0.438207 0.884268 0.252231 0 Uiso 1 H6 H 0.192707 -0.076497 0.285323 0 Uiso 1 H7 H 0.094999 0.132145 0.339288 0 Uiso 1 H8 H 0.171527 0.457518 0.178798 0 Uiso 1 H9 H 0.486491 -0.380167 0.286116 0 Uiso 1 H10 H -0.176969 0.010341 0.320694 0 Uiso 1 H11 H -0.144648 0.580742 0.263504 0 Uiso 1 H12 H -0.515219 1.045513 0.162259 0 Uiso 1 H13 H 0.364488 -0.594976 0.132246 0 Uiso 1 H14 H -0.236931 0.448151 0.009999 0 Uiso 1

H15 H 0.061942 -0.174864 0.036314 0 Uiso 1 H16 H -0.325754 0.658877 0.254154 0 Uiso 1 H17 H -0.014125 0.421529 0.328579 0 Uiso 1 H18 H 0.248952 0.262623 0.148300 0 Uiso 1 H19 H 0.513970 -0.585656 0.215026 0 Uiso 1 H20 H 0.392035 -0.114150 0.259674 0 Uiso 1

#=======================================

# MOLECULAR GEOMETRY _geom_special_details

;

ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

; loop_

_geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance

_geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br1 C4 1.9060(6) yes . . Br2 C13 1.9059(4) yes . . Cu1 O1 2.2698(4) yes . . Cu1 O2 1.9305(5) yes . . Cu1 O3 1.9377(3) yes . . Cu1 N1 1.9845(5) yes . . Cu1 N2 1.9763(3) yes . . O1 C27 1.3841(4) yes . . O7 C24 1.2457(4) yes . . O2 C26 1.3255(2) yes . . O3 C10 1.3270(3) yes . . O4 C22 1.4107(4) yes . . O5 C24 1.4435(3) yes . . O6 C22 1.4491(4) yes . . N1 C21 1.5072(4) yes . . N2 C20 1.3490(3) yes . . N2 C23 1.4992(5) yes . . N1 C19 1.3486(2) yes . . C17 C18 1.4489(5) yes . . C21 C22 1.5767(4) yes . . C21 C23 1.5857(3) yes . . C1 C2 1.4794(3) yes . . C1 C20 1.4328(4) yes . . C1 C26 1.4609(3) yes . . C2 C3 1.4643(4) yes . . C2 C9 1.4502(4) yes . . C3 C4 1.4891(3) yes . . C3 C5 1.4497(2) yes . . C4 C8 1.3759(2) yes . .

(5)

C5 C6 1.4054(4) yes . . C23 C24 1.5817(4) yes . . C6 C7 1.4076(3) yes . . C11 C18 1.4707(3) yes . . C7 C9 1.4006(2) yes . . C8 C26 1.4679(4) yes . . C10 C11 1.4588(5) yes . . C10 C25 1.4682(3) yes . . C11 C19 1.4386(3) yes . . C12 C13 1.4885(5) yes . . C12 C14 1.4507(3) yes . . C12 C18 1.4621(2) yes . . C13 C25 1.3775(2) yes . . C14 C15 1.4061(4) yes . . C15 C16 1.4087(2) yes . . C16 C17 1.3993(3) yes . . O4 H10 1.0291(3) no . . O5 H3 1.0258(3) no . . O1 H8 1.0664(3) no . . C5 H2 1.0700(2) no . . C15 H19 1.09722(19) no . . C6 H12 1.09721(18) no . . C16 H9 0.9467(3) no . . C9 H16 0.8899(2) no . . C17 H20 0.87356(13) no . . C19 H6 1.1072(3) no . . C20 H11 1.1033(2) no . . C7 H5 0.9152(2) no . . C14 H13 0.97374(15) no . . C21 H7 1.1111(3) no . . C8 H14 1.0990(2) no . . C23 H17 1.1130(3) no . . C25 H15 1.0990(3) no . . C27 H1 1.1942(2) no . . C27 H4 1.0319(2) no . . C27 H18 1.1175(2) no . . loop_

_geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle

_geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Br1 C4 C3 124.204(16) yes . . . Br1 C4 C8 114.098(13) yes . . . Br2 C13 C25 113.886(17) yes . . . Br2 C13 C12 124.484(15) yes . . .

Cu1 O3 C10 125.889(16) yes . . . Cu1 O1 C27 118.069(16) yes . . . Cu1 O2 C26 126.093(13) yes . . . Cu1 N1 C19 127.958(11) yes . . . Cu1 N1 C21 104.04(2) yes . . . Cu1 N2 C20 127.864(15) yes . . . Cu1 N2 C23 110.809(16) yes . . . O1 Cu1 O3 95.945(18) yes . . . O2 Cu1 O3 90.016(17) yes . . . O1 Cu1 O2 87.65(2) yes . . . O1 Cu1 N1 99.49(2) yes . . . O1 Cu1 N2 89.736(18) yes . . . O2 Cu1 N1 172.541(3) yes . . . O2 Cu1 N2 91.853(18) yes . . . O3 Cu1 N1 91.361(18) yes . . . O3 Cu1 N2 174.0885(4) yes . . . O4 C22 O6 118.764(19) yes . . . O5 C24 O7 120.804(18) yes . . . O2 C26 C1 127.710(13) yes . . . O7 C24 C23 127.357(17) yes . . . O5 C24 C23 111.837(19) yes . . . O6 C22 C21 140.385(14) yes . . . O4 C22 C21 100.76(2) yes . . . O3 C10 C11 127.937(13) yes . . . O3 C10 C25 116.206(18) yes . . . O2 C26 C8 115.923(15) yes . . . N1 Cu1 N2 86.076(18) yes . . . N2 C23 C24 112.090(19) yes . . . N1 C21 C23 104.317(5) yes . . . N1 C19 C11 122.547(13) yes . . . N2 C20 C1 123.827(16) yes . . . N1 C21 C22 104.47(2) yes . . . N2 C23 C21 104.463(3) yes . . . C19 N1 C21 118.832(11) yes . . . C20 N2 C23 118.743(16) yes . . . C1 C2 C3 120.064(16) yes . . . C12 C18 C17 118.364(14) yes . . . C11 C18 C12 120.978(17) yes . . . C1 C26 C8 116.367(18) yes . . . C2 C1 C20 120.162(15) yes . . . C2 C1 C26 119.503(17) yes . . . C20 C1 C26 120.031(18) yes . . . C10 C11 C18 120.173(15) yes . . . C1 C2 C9 122.383(15) yes . . . C3 C2 C9 117.547(18) yes . . . C2 C3 C4 115.903(17) yes . . . C2 C3 C5 118.120(14) yes . . . C4 C3 C5 125.901(13) yes . . . C3 C4 C8 121.345(14) yes . . .

(6)

C3 C5 C6 120.325(12) yes . . . C4 C8 C26 123.664(12) yes . . . C10 C25 C13 124.132(16) yes . . . C5 C6 C7 120.806(16) yes . . . C2 C9 C7 120.920(13) yes . . . C21 C23 C24 106.924(11) yes . . . C6 C7 C9 120.390(15) yes . . . C13 C12 C14 126.499(12) yes . . . C12 C13 C25 121.430(12) yes . . . C12 C14 C15 120.320(13) yes . . . C10 C11 C19 118.778(18) yes . . . C11 C10 C25 115.726(15) yes . . . C14 C15 C16 121.215(11) yes . . . C11 C18 C17 120.620(15) yes . . . C22 C21 C23 107.990(11) yes . . . C15 C16 C17 120.137(17) yes . . . C18 C11 C19 120.186(16) yes . . . C14 C12 C18 117.832(17) yes . . . C16 C17 C18 120.823(14) yes . . . C13 C12 C18 115.619(14) yes . . . Cu1 O1 H8 99.619(18) no . . . O1 C27 H1 110.175(17) no . . . O1 C27 H4 118.557(19) no . . . O1 C27 H18 100.026(18) no . . . N2 C20 H11 117.872(18) no . . . N1 C21 H7 114.71(2) no . . . N1 C19 H6 118.503(13) no . . . N2 C23 H17 113.21(2) no . . . C27 O1 H8 95.85(2) no . . . C22 O4 H10 89.68(2) no . . .

C24 O5 H3 102.21(2) no . . . C15 C16 H9 106.279(16) no . . . C14 C15 H19 119.297(13) no . . . C16 C15 H19 119.445(17) no . . . C22 C21 H7 112.221(19) no . . . C23 C21 H7 112.451(4) no . . . C15 C14 H13 113.215(11) no . . . C7 C9 H16 116.042(14) no . . . C2 C9 H16 121.184(18) no . . . C12 C14 H13 126.409(16) no . . . C9 C7 H5 116.853(15) no . . . C18 C17 H20 117.868(10) no . . . C7 C6 H12 119.641(14) no . . . C21 C23 H17 111.044(6) no . . . C24 C23 H17 108.890(19) no . . . C6 C7 H5 117.757(17) no . . . C5 C6 H12 119.503(12) no . . . C26 C8 H14 115.952(18) no . . . C6 C5 H2 113.808(16) no . . . C10 C25 H15 115.807(15) no . . . C13 C25 H15 120.030(12) no . . . C4 C8 H14 120.340(15) no . . . C3 C5 H2 125.758(14) no . . . C16 C17 H20 121.118(17) no . . . C11 C19 H6 118.818(17) no . . . C17 C16 H9 117.034(14) no . . . C1 C20 H11 118.273(17) no . . . H1 C27 H4 108.574(16) no . . . H1 C27 H18 112.775(19) no . . . H4 C27 H18 106.539(19) no . . .