#------------------------------------------------------------------------------
#$Date: 2019-11-10 07:49:01 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/57/4515792.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4515792
loop_
_publ_author_name
'Ng, Yik Yie'
'Tan, Lisa Jiaying'
'Ng, Shue Mei'
'Chai, Yoke Tin'
'Ganguly, Rakesh'
'Du, Yonghua'
'Yeow, Edwin Kok Lee'
'Soo, Han Sen'
_publ_section_title
;
 Spectroscopic Characterization and Mechanistic Studies on Visible Light
 Photoredox Carbon--Carbon Bond Formation by Bis(arylimino)acenaphthene
 Copper Photosensitizers
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              11277
_journal_paper_doi               10.1021/acscatal.8b02502
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C60 H42 Br2 Cu F12 N6 O8 Sb2'
_chemical_formula_weight         1669.85
_chemical_name_common            shs302m
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 92.097(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7665(11)
_cell_length_b                   26.084(3)
_cell_length_c                   21.8320(18)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.6018
_cell_measurement_theta_min      2.9137
_cell_volume                     6696.1(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31030
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.43
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3268
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         2.638
_refine_diff_density_min         -1.891
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5831
_refine_ls_number_restraints     989
_refine_ls_restrained_S_all      1.920
_refine_ls_R_factor_all          0.2371
_refine_ls_R_factor_gt           0.1755
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4966
_refine_ls_wR_factor_ref         0.5348
_reflns_number_gt                3267
_reflns_number_total             5831
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b02502_si_003.cif
_cod_data_source_block           shs302m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515792
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.0768(16) -0.0260(8) -0.0720(9) 0.119(5) Uani d U . D 1 . .
C C19 0.158(2) -0.0133(7) -0.0255(13) 0.115(4) Uani d U . D 1 . .
O O4 0.2220(17) -0.0373(8) 0.0045(9) 0.126(5) Uani d U . D 1 . .
C C20 0.236(3) -0.0889(9) -0.0119(16) 0.136(8) Uani d U . D 1 . .
H H20A 0.16617 -0.107934 -0.003583 0.204 Uiso calc U . R 1 . .
H H20B 0.299773 -0.103656 0.012057 0.204 Uiso calc U . R 1 . .
H H20C 0.250886 -0.091153 -0.055666 0.204 Uiso calc U . R 1 . .
O O1 -0.0430(19) 0.5257(10) 0.0833(11) 0.146(6) Uani d U . D 1 . .
C C27 0.063(2) 0.5094(8) 0.1113(15) 0.131(5) Uani d U . D 1 . .
O O2 0.1273(17) 0.5323(8) 0.1437(10) 0.136(5) Uani d U . D 1 . .
C C28 0.089(3) 0.5829(9) 0.1545(17) 0.144(8) Uani d U . D 1 . .
H H28A 0.144943 0.600653 0.181505 0.216 Uiso calc U . R 1 . .
H H28B 0.08124 0.601318 0.115477 0.216 Uiso calc U . R 1 . .
H H28C 0.01578 0.581758 0.174053 0.216 Uiso calc U . R 1 . .
Br Br1 -0.2688(3) 0.2361(2) 0.28929(18) 0.0885(16) Uani d U P D 0.5 A 1
Br Br2 -0.2687(4) 0.1658(3) 0.2743(2) 0.120(2) Uani d U P D 0.5 A 2
C C1 0.0808(13) 0.2722(9) 0.0926(7) 0.065(3) Uani d U . . 1 . .
C C2 -0.1689(10) 0.2583(4) 0.2241(6) 0.091(4) Uani d U . DG 1 . .
C C3 -0.1365(11) 0.3076(5) 0.2121(6) 0.090(4) Uani d U . G 1 A .
H H3 -0.170494 0.335377 0.232884 0.108 Uiso calc U . R 1 . .
C C4 -0.0552(10) 0.3169(5) 0.1703(6) 0.084(4) Uani d U . G 1 A .
H H4 -0.032678 0.35112 0.161966 0.101 Uiso calc U . R 1 . .
C C5 -0.0062(9) 0.2769(4) 0.1403(5) 0.076(3) Uani d U . G 1 A .
C C6 -0.0386(6) 0.2276(3) 0.1523(4) 0.084(3) Uani d U . G 1 A .
C C7 -0.1199(7) 0.2183(3) 0.1942(4) 0.090(3) Uani d U . DG 1 A .
C C8 -0.1523(10) 0.1690(4) 0.2061(5) 0.096(4) Uani d U . DG 1 A .
C C9 -0.1034(10) 0.1290(5) 0.1762(6) 0.097(4) Uani d U . G 1 A .
H H9 -0.125838 0.094808 0.184534 0.116 Uiso calc U . R 1 . .
C C10 -0.0220(10) 0.1383(5) 0.1344(6) 0.087(4) Uani d U . G 1 A .
H H10 0.011917 0.110576 0.113585 0.105 Uiso calc U . R 1 . .
C C11 0.0104(9) 0.1876(4) 0.1224(5) 0.079(3) Uani d U . G 1 A .
C C12 0.0833(16) 0.2115(8) 0.0802(9) 0.067(3) Uani d U . . 1 . .
C C13 0.1535(12) 0.1443(4) 0.0252(7) 0.077(3) Uani d U . G 1 . .
C C18 0.2299(11) 0.1108(5) 0.0542(6) 0.088(4) Uani d U . G 1 . .
H H18 0.280759 0.122968 0.085732 0.106 Uiso calc U . R 1 . .
C C17 0.2318(12) 0.0595(5) 0.0372(7) 0.098(4) Uani d U . DG 1 . .
H H17 0.283937 0.036562 0.057025 0.117 Uiso calc U . R 1 . .
C C16 0.1573(13) 0.0417(4) -0.0089(7) 0.102(4) Uani d U . DG 1 . .
C C15 0.0810(12) 0.0752(5) -0.0380(6) 0.097(4) Uani d U . DG 1 . .
H H15 0.030067 0.063011 -0.06951 0.116 Uiso calc U . R 1 . .
C C14 0.0791(11) 0.1265(5) -0.0209(7) 0.087(4) Uani d U . G 1 . .
H H14 0.026887 0.149417 -0.040803 0.105 Uiso calc U . R 1 . .
Sb Sb1 0.75 0.25 0 0.0744(8) Uani d U P S 1 . .
C C21 0.1338(13) 0.3525(5) 0.0767(7) 0.079(3) Uani d U . G 1 . .
C C26 0.2011(11) 0.3793(6) 0.1194(7) 0.089(4) Uani d U . G 1 . .
H H26 0.261758 0.36237 0.141077 0.106 Uiso calc U . R 1 . .
C C25 0.1796(12) 0.4308(6) 0.1305(7) 0.100(4) Uani d U . DG 1 . .
H H25 0.225562 0.449078 0.15975 0.12 Uiso calc U . R 1 . .
C C24 0.0908(14) 0.4555(5) 0.0989(8) 0.114(4) Uani d U . DG 1 . .
C C23 0.0235(12) 0.4287(6) 0.0561(8) 0.110(4) Uani d U . DG 1 . .
H H23 -0.037138 0.445608 0.034456 0.132 Uiso calc U . R 1 . .
C C22 0.0450(12) 0.3772(6) 0.0450(7) 0.095(4) Uani d U . G 1 . .
H H22 -0.000944 0.358899 0.015782 0.114 Uiso calc U . R 1 . .
C C29 0.4615(17) 0.2415(7) 0.1058(9) 0.060(4) Uani d U . . 1 . .
C C30 0.5474(17) 0.2378(8) 0.1453(10) 0.066(4) Uani d U . . 1 . .
H H30A 0.596694 0.267824 0.141681 0.099 Uiso calc U . R 1 . .
H H30B 0.590774 0.206653 0.136923 0.099 Uiso calc U . R 1 . .
H H30C 0.519052 0.236098 0.186923 0.099 Uiso calc U . R 1 . .
N N1 0.1392(11) 0.3001(7) 0.0645(6) 0.064(3) Uani d U . . 1 . .
N N2 0.1546(12) 0.1967(6) 0.0378(7) 0.064(3) Uani d U . . 1 . .
N N3 0.3765(13) 0.2407(5) 0.0718(7) 0.058(3) Uani d U . . 1 . .
Cu Cu1 0.25 0.25 0 0.0430(8) Uani d . P S 1 . .
Sb Sb2 0.5 0.37816(15) 0.25 0.1276(14) Uani d TU P S 1 . .
F F1 0.7353(12) 0.1987(5) 0.0512(6) 0.098(4) Uani d U . D 1 . .
F F2 0.7599(11) 0.2937(5) 0.0609(6) 0.093(3) Uani d U . D 1 . .
F F3 0.9000(10) 0.2428(5) 0.0015(6) 0.098(4) Uani d U . D 1 . .
F F4 0.5764(14) 0.3721(7) 0.1816(10) 0.162(6) Uani d U . D 1 . .
F F5 0.4110(14) 0.3250(7) 0.2249(10) 0.149(5) Uani d U . D 1 . .
F F6 0.4082(16) 0.4228(7) 0.2179(10) 0.172(6) Uani d U . D 1 . .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O4 C19 O3 . . 133.4(19)
O4 C19 C16 . . 113.2(17)
O3 C19 C16 . . 113.3(15)
C19 O4 C20 . . 117.(2)
O2 C27 O1 . . 129.5(19)
O2 C27 C24 . . 116.8(17)
O1 C27 C24 . . 113.7(16)
C27 O2 C28 . . 112.(2)
N1 C1 C5 . . 137.(2)
N1 C1 C12 . . 120.1(17)
C5 C1 C12 . . 102.5(15)
C7 C2 C3 . . 120.0
C7 C2 Br1 . . 113.2(4)
C3 C2 Br1 . . 126.3(4)
C4 C3 C2 . . 120.0
C5 C4 C3 . . 120.0
C6 C5 C4 . . 120.0
C6 C5 C1 . . 105.0(10)
C4 C5 C1 . . 135.0(10)
C5 C6 C7 . . 120.0
C5 C6 C11 . . 120.0
C7 C6 C11 . . 120.0
C2 C7 C6 . . 120.0
C2 C7 C8 . . 120.0
C6 C7 C8 . . 120.0
C7 C8 C9 . . 120.0
C7 C8 Br2 . . 111.9(4)
C9 C8 Br2 . . 128.0(4)
C8 C9 C10 . . 120.0
C11 C10 C9 . . 120.0
C10 C11 C6 . . 120.0
C10 C11 C12 . . 135.4(10)
C6 C11 C12 . . 104.4(10)
N2 C12 C11 . . 137.1(19)
N2 C12 C1 . . 114.9(16)
C11 C12 C1 . . 107.8(14)
C18 C13 C14 . . 120.0
C18 C13 N2 . . 121.7(11)
C14 C13 N2 . . 118.1(11)
C13 C18 C17 . . 120.0
C16 C17 C18 . . 120.0
C17 C16 C15 . . 120.0
C17 C16 C19 . . 119.5(7)
C15 C16 C19 . . 120.5(7)
C14 C15 C16 . . 120.0
C15 C14 C13 . . 120.0
F2 Sb1 F2 7_655 . 180.0
F2 Sb1 F1 7_655 . 89.0(6)
F2 Sb1 F1 . . 91.0(6)
F2 Sb1 F1 7_655 7_655 91.0(6)
F2 Sb1 F1 . 7_655 89.0(6)
F1 Sb1 F1 . 7_655 180.0
F2 Sb1 F3 7_655 7_655 90.9(6)
F2 Sb1 F3 . 7_655 89.1(6)
F1 Sb1 F3 . 7_655 88.4(6)
F1 Sb1 F3 7_655 7_655 91.6(6)
F2 Sb1 F3 7_655 . 89.1(6)
F2 Sb1 F3 . . 90.9(6)
F1 Sb1 F3 . . 91.6(6)
F1 Sb1 F3 7_655 . 88.4(6)
F3 Sb1 F3 7_655 . 180.0
C26 C21 C22 . . 120.0
C26 C21 N1 . . 126.3(11)
C22 C21 N1 . . 113.5(11)
C25 C26 C21 . . 120.0
C26 C25 C24 . . 120.0
C23 C24 C25 . . 120.0
C23 C24 C27 . . 118.6(8)
C25 C24 C27 . . 121.4(8)
C24 C23 C22 . . 120.0
C23 C22 C21 . . 120.0
N3 C29 C30 . . 173.(2)
C1 N1 C21 . . 118.1(17)
C1 N1 Cu1 . . 108.3(15)
C21 N1 Cu1 . . 133.6(11)
C12 N2 C13 . . 115.0(16)
C12 N2 Cu1 . . 117.8(14)
C13 N2 Cu1 . . 127.3(12)
C29 N3 Cu1 . . 167.3(15)
N2 Cu1 N2 . 7 180.0
N2 Cu1 N3 . . 90.3(6)
N2 Cu1 N3 7 . 89.7(6)
N2 Cu1 N3 . 7 89.7(6)
N2 Cu1 N3 7 7 90.3(6)
N3 Cu1 N3 . 7 180.0
N2 Cu1 N1 . 7 101.2(6)
N2 Cu1 N1 7 7 78.8(6)
N3 Cu1 N1 . 7 89.4(5)
N3 Cu1 N1 7 7 90.6(5)
N2 Cu1 N1 . . 78.8(6)
N2 Cu1 N1 7 . 101.2(6)
N3 Cu1 N1 . . 90.6(5)
N3 Cu1 N1 7 . 89.4(5)
N1 Cu1 N1 7 . 180.0
F6 Sb2 F6 2_655 . 94.8(14)
F6 Sb2 F4 2_655 . 94.2(10)
F6 Sb2 F4 . . 92.7(8)
F6 Sb2 F4 2_655 2_655 92.7(8)
F6 Sb2 F4 . 2_655 94.2(10)
F4 Sb2 F4 . 2_655 169.8(13)
F6 Sb2 F5 2_655 2_655 92.7(8)
F6 Sb2 F5 . 2_655 171.7(10)
F4 Sb2 F5 . 2_655 83.2(9)
F4 Sb2 F5 2_655 2_655 89.0(8)
F6 Sb2 F5 2_655 . 171.7(10)
F6 Sb2 F5 . . 92.7(8)
F4 Sb2 F5 . . 89.0(8)
F4 Sb2 F5 2_655 . 83.2(9)
F5 Sb2 F5 2_655 . 80.1(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O3 C19 . 1.41(2)
C19 O4 . 1.16(2)
C19 C16 . 1.478(14)
O4 C20 . 1.404(15)
O1 C27 . 1.43(2)
C27 O2 . 1.18(2)
C27 C24 . 1.472(14)
O2 C28 . 1.415(15)
Br1 C2 . 1.966(10)
Br2 C8 . 2.060(10)
C1 N1 . 1.19(2)
C1 C5 . 1.49(2)
C1 C12 . 1.61(3)
C2 C7 . 1.369(5)
C2 C3 . 1.369(5)
C3 C4 . 1.369(5)
C4 C5 . 1.369(5)
C5 C6 . 1.369(5)
C6 C7 . 1.369(5)
C6 C11 . 1.369(5)
C7 C8 . 1.369(5)
C8 C9 . 1.369(5)
C9 C10 . 1.369(5)
C10 C11 . 1.369(5)
C11 C12 . 1.43(2)
C12 N2 . 1.33(2)
C13 C18 . 1.39
C13 C14 . 1.39
C13 N2 . 1.393(19)
C18 C17 . 1.39
C17 C16 . 1.39
C16 C15 . 1.39
C15 C14 . 1.39
Sb1 F2 7_655 1.753(12)
Sb1 F2 . 1.753(12)
Sb1 F1 . 1.757(12)
Sb1 F1 7_655 1.757(12)
Sb1 F3 7_655 1.774(12)
Sb1 F3 . 1.774(12)
C21 C26 . 1.39
C21 C22 . 1.39
C21 N1 . 1.39(2)
C26 C25 . 1.39
C25 C24 . 1.39
C24 C23 . 1.39
C23 C22 . 1.39
C29 N3 . 1.22(3)
C29 C30 . 1.31(3)
N1 Cu1 . 2.350(16)
N2 Cu1 . 1.986(15)
N3 Cu1 . 2.136(16)
Sb2 F6 2_655 1.719(18)
Sb2 F6 . 1.719(18)
Sb2 F4 . 1.778(18)
Sb2 F4 2_655 1.778(18)
Sb2 F5 2_655 1.810(18)
Sb2 F5 . 1.810(18)
