#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:12:08 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/04/7060431.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_7060431
loop_
_publ_author_name
'Xia, Youfu'
'Du, Yanqing'
'Xiang, Qian'
'Humphrey, Mark G.'
_publ_section_title
;
 Highly efficient room-temperature phosphorescent materials with a
 heavy-atom effect of bromine
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4930
_journal_page_last               4933
_journal_paper_doi               10.1039/D0NJ05713D
_journal_volume                  45
_journal_year                    2021
_chemical_formula_sum            'C45 H32 Br N3'
_chemical_formula_weight         694.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-08-13 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                68.612(2)
_cell_angle_beta                 80.333(3)
_cell_angle_gamma                86.144(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6776(4)
_cell_length_b                   13.1444(5)
_cell_length_c                   15.7153(6)
_cell_measurement_reflns_used    5244
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.9129
_cell_measurement_theta_min      2.8964
_cell_volume                     1645.33(12)
_computing_cell_refinement       'Bruker APEX2(Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker APEX2(Bruker AXS Inc., 2015)'
_computing_data_reduction        'Bruker APEX2(Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10838
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.155
_diffrn_reflns_theta_min         2.896
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.6598
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0229P)²+1.0899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4826
_reflns_number_total             6517
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj05713d2.cif
_cod_data_source_block           S_a
_cod_depositor_comments
'Adding full bibliography for 7060430--7060431.cif.'
_cod_database_code               7060431
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.870
_shelx_estimated_absorpt_t_max   0.932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21846(4) -0.10269(3) 0.81804(2) 0.02951(11) Uani 1 1 d . . . . .
N1 N 0.3835(3) 0.4480(2) 0.67734(18) 0.0297(6) Uani 1 1 d . . . . .
C1 C 0.2503(3) 0.0514(2) 0.75852(19) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.2029(3) 0.1041(2) 0.67227(19) 0.0183(6) Uani 1 1 d . . . . .
N2 N 0.4414(3) 0.1158(2) 0.93051(16) 0.0211(5) Uani 1 1 d . . . . .
C3 C 0.2215(3) 0.2164(2) 0.63222(19) 0.0199(6) Uani 1 1 d . . . . .
H3 H 0.190693 0.253878 0.574918 0.024 Uiso 1 1 calc R U . . .
N3 N 0.0828(3) 0.1043(2) 0.53865(16) 0.0228(6) Uani 1 1 d . . . . .
C4 C 0.2856(3) 0.2736(2) 0.67662(19) 0.0205(6) Uani 1 1 d . . . . .
C6 C 0.3143(3) 0.1063(2) 0.80428(19) 0.0181(6) Uani 1 1 d . . . . .
C5 C 0.3332(3) 0.2185(2) 0.76108(19) 0.0196(6) Uani 1 1 d . . . . .
H5 H 0.378553 0.257088 0.789585 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3702(4) 0.1905(2) 0.96885(19) 0.0229(7) Uani 1 1 d . . . . .
C8 C 0.3008(4) 0.3962(2) 0.6313(2) 0.0329(8) Uani 1 1 d . . . . .
H00A H 0.354338 0.413263 0.568401 0.039 Uiso 1 1 calc R U . . .
H00B H 0.196685 0.427814 0.627849 0.039 Uiso 1 1 calc R U . . .
C7 C 0.3598(4) 0.0468(2) 0.89974(19) 0.0241(7) Uani 1 1 d . . . . .
H7A H 0.266090 0.019044 0.943860 0.029 Uiso 1 1 calc R U . . .
H7AB H 0.425902 -0.015272 0.898301 0.029 Uiso 1 1 calc R U . . .
C47 C 0.3140(4) 0.4980(2) 0.7388(2) 0.0285(8) Uani 1 1 d . . . . .
C46 C 0.1602(4) 0.4966(3) 0.7809(2) 0.0373(9) Uani 1 1 d . . . . .
H46 H 0.084249 0.458941 0.769133 0.045 Uiso 1 1 calc R U . . .
C45 C 0.1227(5) 0.5525(3) 0.8405(3) 0.0439(9) Uani 1 1 d . . . . .
H45 H 0.020085 0.552456 0.869607 0.053 Uiso 1 1 calc R U . . .
C44 C 0.2376(5) 0.6096(3) 0.8580(3) 0.0429(9) Uani 1 1 d . . . . .
H44 H 0.209830 0.646867 0.898513 0.052 Uiso 1 1 calc R U . . .
C43 C 0.3896(4) 0.6113(3) 0.8163(2) 0.0352(8) Uani 1 1 d . . . . .
H43 H 0.464268 0.650314 0.827607 0.042 Uiso 1 1 calc R U . . .
C42 C 0.4313(4) 0.5539(2) 0.7567(2) 0.0302(8) Uani 1 1 d . . . . .
C41 C 0.5770(4) 0.5360(2) 0.7041(2) 0.0299(8) Uani 1 1 d . . . . .
C40 C 0.7301(4) 0.5699(3) 0.6917(3) 0.0397(9) Uani 1 1 d . . . . .
H40 H 0.755073 0.614694 0.721427 0.048 Uiso 1 1 calc R U . . .
C39 C 0.8446(5) 0.5366(3) 0.6351(3) 0.0457(10) Uani 1 1 d . . . . .
H39 H 0.946143 0.561837 0.624568 0.055 Uiso 1 1 calc R U . . .
C38 C 0.8098(5) 0.4658(3) 0.5938(3) 0.0470(10) Uani 1 1 d . . . . .
H38 H 0.889900 0.440549 0.559071 0.056 Uiso 1 1 calc R U . . .
C37 C 0.6571(5) 0.4319(3) 0.6034(2) 0.0392(9) Uani 1 1 d . . . . .
H37 H 0.633257 0.386020 0.574356 0.047 Uiso 1 1 calc R U . . .
C36 C 0.5429(4) 0.4688(2) 0.6575(2) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.2145(4) 0.2000(3) 1.0043(2) 0.0291(7) Uani 1 1 d . . . . .
H10 H 0.139701 0.151605 1.005944 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1746(4) 0.2839(3) 1.0371(2) 0.0380(9) Uani 1 1 d . . . . .
H11 H 0.071010 0.292547 1.060867 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2875(5) 0.3563(3) 1.0353(2) 0.0425(9) Uani 1 1 d . . . . .
H12 H 0.257682 0.411752 1.058381 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4399(4) 0.3469(3) 1.0003(2) 0.0357(8) Uani 1 1 d . . . . .
H13 H 0.513570 0.395871 0.999153 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4850(4) 0.2636(3) 0.9664(2) 0.0254(7) Uani 1 1 d . . . . .
C15 C 0.6299(4) 0.2325(3) 0.9235(2) 0.0271(7) Uani 1 1 d . . . . .
C16 C 0.5982(4) 0.1425(2) 0.90058(19) 0.0239(7) Uani 1 1 d . . . . .
C17 C 0.7143(4) 0.0913(3) 0.8574(2) 0.0349(8) Uani 1 1 d . . . . .
H17 H 0.691828 0.032617 0.841903 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8986(5) 0.2197(4) 0.8608(3) 0.0513(11) Uani 1 1 d . . . . .
H19 H 1.000823 0.244756 0.847018 0.062 Uiso 1 1 calc R U . . .
C18 C 0.8645(4) 0.1316(4) 0.8384(2) 0.0499(11) Uani 1 1 d . . . . .
H18 H 0.944751 0.098844 0.810042 0.060 Uiso 1 1 calc R U . . .
C20 C 0.7835(4) 0.2705(3) 0.9029(2) 0.0414(9) Uani 1 1 d . . . . .
H20 H 0.807597 0.329424 0.917594 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1316(4) 0.0398(2) 0.6262(2) 0.0263(7) Uani 1 1 d . . . . .
H21A H 0.207243 -0.014204 0.616500 0.032 Uiso 1 1 calc R U . . .
H21B H 0.041583 0.000776 0.668019 0.032 Uiso 1 1 calc R U . . .
C23 C 0.1715(4) 0.1194(2) 0.4526(2) 0.0226(7) Uani 1 1 d . . . . .
C24 C 0.3266(4) 0.0941(3) 0.4319(2) 0.0335(8) Uani 1 1 d . . . . .
H24 H 0.388220 0.063611 0.478231 0.040 Uiso 1 1 calc R U . . .
C25 C 0.3875(4) 0.1155(3) 0.3399(3) 0.0394(9) Uani 1 1 d . . . . .
H25 H 0.492305 0.100494 0.323815 0.047 Uiso 1 1 calc R U . . .
C26 C 0.2932(4) 0.1595(3) 0.2706(2) 0.0377(9) Uani 1 1 d . . . . .
H26 H 0.335340 0.170957 0.209372 0.045 Uiso 1 1 calc R U . . .
C27 C 0.1394(4) 0.1861(3) 0.2918(2) 0.0299(8) Uani 1 1 d . . . . .
H27 H 0.077885 0.216195 0.245420 0.036 Uiso 1 1 calc R U . . .
C28 C 0.0765(4) 0.1672(2) 0.3841(2) 0.0228(7) Uani 1 1 d . . . . .
C29 C -0.0761(4) 0.1833(2) 0.4306(2) 0.0228(7) Uani 1 1 d . . . . .
C30 C -0.2187(4) 0.2263(3) 0.4016(2) 0.0287(7) Uani 1 1 d . . . . .
H30 H -0.226399 0.255089 0.338902 0.034 Uiso 1 1 calc R U . . .
C31 C -0.3468(4) 0.2258(3) 0.4661(3) 0.0357(8) Uani 1 1 d . . . . .
H31 H -0.441290 0.254555 0.446829 0.043 Uiso 1 1 calc R U . . .
C32 C -0.3370(4) 0.1826(3) 0.5605(3) 0.0370(8) Uani 1 1 d . . . . .
H32 H -0.425982 0.181162 0.603160 0.044 Uiso 1 1 calc R U . . .
C33 C -0.1969(4) 0.1416(3) 0.5918(2) 0.0318(8) Uani 1 1 d . . . . .
H33 H -0.189797 0.114604 0.654603 0.038 Uiso 1 1 calc R U . . .
C34 C -0.0684(4) 0.1424(2) 0.5262(2) 0.0225(7) Uani 1 1 d . . . . .
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'
N N 0.0061 0.0033 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C36 N1 C47 109.0(3) . . ?
C36 N1 C8 125.0(3) . . ?
C47 N1 C8 125.5(3) . . ?
C6 C1 C2 122.9(3) . . ?
C6 C1 Br1 118.5(2) . . ?
C2 C1 Br1 118.6(2) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 C21 122.0(2) . . ?
C1 C2 C21 120.5(2) . . ?
C16 N2 C9 108.4(2) . . ?
C16 N2 C7 123.8(3) . . ?
C9 N2 C7 124.9(3) . . ?
C2 C3 C4 120.8(3) . . ?
C23 N3 C34 108.9(2) . . ?
C23 N3 C21 124.6(3) . . ?
C34 N3 C21 125.4(3) . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 C8 121.0(3) . . ?
C3 C4 C8 119.0(3) . . ?
C1 C6 C5 117.7(2) . . ?
C1 C6 C7 121.5(2) . . ?
C5 C6 C7 120.7(2) . . ?
C4 C5 C6 121.0(3) . . ?
C10 C9 N2 129.6(3) . . ?
C10 C9 C14 121.6(3) . . ?
N2 C9 C14 108.7(3) . . ?
N1 C8 C4 115.4(2) . . ?
N2 C7 C6 112.8(2) . . ?
C46 C47 N1 130.1(3) . . ?
C46 C47 C42 121.6(3) . . ?
N1 C47 C42 108.3(3) . . ?
C45 C46 C47 118.2(3) . . ?
C46 C45 C44 120.8(4) . . ?
C43 C44 C45 121.1(4) . . ?
C44 C43 C42 119.3(3) . . ?
C43 C42 C47 118.9(3) . . ?
C43 C42 C41 134.0(3) . . ?
C47 C42 C41 107.1(3) . . ?
C40 C41 C36 118.7(3) . . ?
C40 C41 C42 134.6(3) . . ?
C36 C41 C42 106.7(3) . . ?
C39 C40 C41 119.6(3) . . ?
C40 C39 C38 120.6(4) . . ?
C39 C38 C37 121.1(4) . . ?
C36 C37 C38 117.6(3) . . ?
C37 C36 N1 128.9(3) . . ?
C37 C36 C41 122.2(3) . . ?
N1 C36 C41 109.0(3) . . ?
C11 C10 C9 117.6(3) . . ?
C10 C11 C12 121.2(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C14 119.6(3) . . ?
C13 C14 C9 118.9(3) . . ?
C13 C14 C15 134.1(3) . . ?
C9 C14 C15 106.9(3) . . ?
C20 C15 C16 118.7(3) . . ?
C20 C15 C14 134.4(3) . . ?
C16 C15 C14 106.9(3) . . ?
N2 C16 C17 128.8(3) . . ?
N2 C16 C15 109.0(3) . . ?
C17 C16 C15 122.2(3) . . ?
C18 C17 C16 117.1(4) . . ?
C20 C19 C18 121.0(4) . . ?
C17 C18 C19 121.7(4) . . ?
C19 C20 C15 119.3(4) . . ?
N3 C21 C2 115.1(2) . . ?
C24 C23 N3 128.8(3) . . ?
C24 C23 C28 122.4(3) . . ?
N3 C23 C28 108.7(3) . . ?
C23 C24 C25 117.7(3) . . ?
C24 C25 C26 120.9(3) . . ?
C27 C26 C25 120.9(3) . . ?
C26 C27 C28 119.1(3) . . ?
C27 C28 C23 118.9(3) . . ?
C27 C28 C29 133.9(3) . . ?
C23 C28 C29 107.1(3) . . ?
C30 C29 C34 118.4(3) . . ?
C30 C29 C28 134.7(3) . . ?
C34 C29 C28 106.8(3) . . ?
C31 C30 C29 119.7(3) . . ?
C30 C31 C32 120.7(3) . . ?
C33 C32 C31 121.3(3) . . ?
C34 C33 C32 117.5(3) . . ?
C33 C34 N3 129.3(3) . . ?
C33 C34 C29 122.3(3) . . ?
N3 C34 C29 108.4(3) . . ?
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
Br1 C1 1.914(3) . ?
N1 C36 1.389(4) . ?
N1 C47 1.393(4) . ?
N1 C8 1.451(4) . ?
C1 C6 1.382(4) . ?
C1 C2 1.396(4) . ?
C2 C3 1.385(4) . ?
C2 C21 1.514(4) . ?
N2 C16 1.387(4) . ?
N2 C9 1.390(4) . ?
N2 C7 1.443(4) . ?
C3 C4 1.390(4) . ?
N3 C23 1.391(4) . ?
N3 C34 1.392(4) . ?
N3 C21 1.444(4) . ?
C4 C5 1.378(4) . ?
C4 C8 1.510(4) . ?
C6 C5 1.389(4) . ?
C6 C7 1.523(4) . ?
C9 C10 1.389(4) . ?
C9 C14 1.416(4) . ?
C47 C46 1.385(5) . ?
C47 C42 1.416(4) . ?
C46 C45 1.374(5) . ?
C45 C44 1.406(5) . ?
C44 C43 1.368(5) . ?
C43 C42 1.393(5) . ?
C42 C41 1.445(5) . ?
C41 C40 1.389(5) . ?
C41 C36 1.409(4) . ?
C40 C39 1.377(5) . ?
C39 C38 1.386(5) . ?
C38 C37 1.393(5) . ?
C37 C36 1.375(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.400(5) . ?
C12 C13 1.361(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.431(4) . ?
C15 C20 1.399(5) . ?
C15 C16 1.412(4) . ?
C16 C17 1.393(4) . ?
C17 C18 1.385(5) . ?
C19 C20 1.375(5) . ?
C19 C18 1.389(6) . ?
C23 C24 1.378(5) . ?
C23 C28 1.402(4) . ?
C24 C25 1.385(5) . ?
C25 C26 1.403(5) . ?
C26 C27 1.374(5) . ?
C27 C28 1.398(4) . ?
C28 C29 1.443(4) . ?
C29 C30 1.402(4) . ?
C29 C34 1.412(4) . ?
C30 C31 1.372(5) . ?
C31 C32 1.397(5) . ?
C32 C33 1.389(5) . ?
C33 C34 1.384(4) . ?
