#------------------------------------------------------------------------------
#$Date: 2021-07-06 04:26:30 +0300 (Tue, 06 Jul 2021) $
#$Revision: 267261 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563955.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_1563955
loop_
_publ_author_name
'Xiong, Zuping'
'Zhang, Xiaoxiao'
'Liu, Longxiang'
'Zhu, Qiaozhi'
'Wang, Zhenni'
'Feng, Hui'
'Qian, Zhaosheng'
_publ_section_title
;
 Achieving Highly Efficient Aggregation-Induced Emission, Reversible and
 Irreversible Photochromism by Heavy Halogen-Regulated Photophysics and
 D-A Molecular Pattern-Controlled Photochemistry of Through-Space
 Conjugated Lumingens
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02168K
_journal_year                    2021
_chemical_formula_moiety         'C25 H24 Br N3'
_chemical_formula_sum            'C25 H24 Br N3'
_chemical_formula_weight         446.38
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-01-06 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                102.009(3)
_cell_angle_beta                 94.363(3)
_cell_angle_gamma                114.749(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8541(6)
_cell_length_b                   10.6234(6)
_cell_length_c                   11.7377(7)
_cell_measurement_reflns_used    7837
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.19
_cell_volume                     1072.89(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.48
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19279
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         2.189
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0778 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.3514.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0322
_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)+(0.0421P)²+0.3902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3674
_reflns_number_total             4427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc02168k2.cif
_cod_data_source_block           mo_0114_1_0m
_cod_database_code               1563955
_shelx_shelxl_version_number     2018/3
_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_max   0.830
_shelx_estimated_absorpt_t_min   0.699
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G),
 C00I(H00I), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00Q(H00E,H00F,H00H), C00R(H00J,H00K,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,
 H00V,H00W)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br01 Br 0.20934(3) -0.02275(2) 0.31310(2) 0.04829(10) Uani 1 1 d . . . . .
N002 N 0.7167(2) 0.54340(19) 0.05145(17) 0.0411(4) Uani 1 1 d . . . . .
N003 N 0.8560(2) 1.1830(2) 0.08846(18) 0.0429(4) Uani 1 1 d . . . . .
N004 N 0.0291(2) 0.6643(2) 0.46828(18) 0.0526(5) Uani 1 1 d . . . . .
C005 C 0.5245(2) 0.6844(2) 0.23985(17) 0.0324(4) Uani 1 1 d . . . . .
C006 C 0.5402(2) 0.5615(2) 0.19964(18) 0.0323(4) Uani 1 1 d . . . . .
C007 C 0.6413(2) 0.5566(2) 0.11771(18) 0.0341(4) Uani 1 1 d . . . . .
C008 C 0.3974(2) 0.6804(2) 0.30155(18) 0.0322(4) Uani 1 1 d . . . . .
C009 C 0.7723(2) 0.8666(2) 0.20315(19) 0.0349(4) Uani 1 1 d . . . . .
H009 H 0.822883 0.812930 0.222929 0.042 Uiso 1 1 calc R . . . .
C00A C 0.3362(2) 0.1603(2) 0.16448(19) 0.0367(5) Uani 1 1 d . . . . .
H00A H 0.305727 0.073452 0.104491 0.044 Uiso 1 1 calc R . . . .
C00B C 0.4202(2) 0.7735(2) 0.41198(18) 0.0341(4) Uani 1 1 d . . . . .
H00B H 0.520655 0.842416 0.449550 0.041 Uiso 1 1 calc R . . . .
C00C C 0.2482(2) 0.5851(2) 0.24715(18) 0.0364(5) Uani 1 1 d . . . . .
H00C H 0.229342 0.521437 0.171380 0.044 Uiso 1 1 calc R . . . .
C00D C 0.5537(2) 0.9099(2) 0.19205(19) 0.0350(4) Uani 1 1 d . . . . .
H00D H 0.453088 0.887202 0.205052 0.042 Uiso 1 1 calc R . . . .
C00E C 0.6192(2) 0.8210(2) 0.21358(18) 0.0323(4) Uani 1 1 d . . . . .
C00F C 0.1493(3) 0.6711(2) 0.41361(19) 0.0376(5) Uani 1 1 d . . . . .
C00G C 0.6312(2) 1.0299(2) 0.15245(19) 0.0366(5) Uani 1 1 d . . . . .
H00G H 0.582258 1.086605 0.137206 0.044 Uiso 1 1 calc R . . . .
C00H C 0.3064(2) 0.1569(2) 0.2772(2) 0.0363(5) Uani 1 1 d . . . . .
C00I C 0.4110(2) 0.2918(2) 0.14015(19) 0.0344(4) Uani 1 1 d . . . . .
H00I H 0.432299 0.294408 0.062848 0.041 Uiso 1 1 calc R . . . .
C00J C 0.7813(2) 1.0693(2) 0.13437(18) 0.0345(4) Uani 1 1 d . . . . .
C00K C 0.4562(2) 0.4215(2) 0.22700(18) 0.0326(4) Uani 1 1 d . . . . .
C00L C 0.3007(3) 0.7678(2) 0.46786(19) 0.0365(5) Uani 1 1 d . . . . .
H00L H 0.320648 0.830245 0.544429 0.044 Uiso 1 1 calc R . . . .
C00M C 0.1272(3) 0.5809(2) 0.30047(19) 0.0390(5) Uani 1 1 d . . . . .
H00M H 0.026671 0.515857 0.260041 0.047 Uiso 1 1 calc R . . . .
C00N C 0.8517(2) 0.9870(2) 0.16506(19) 0.0351(4) Uani 1 1 d . . . . .
H00N H 0.955468 1.014737 0.159464 0.042 Uiso 1 1 calc R . . . .
C00O C 0.4226(3) 0.4132(2) 0.33951(19) 0.0367(5) Uani 1 1 d . . . . .
H00O H 0.450669 0.499423 0.399658 0.044 Uiso 1 1 calc R . . . .
C00P C 0.3497(3) 0.2826(2) 0.3653(2) 0.0384(5) Uani 1 1 d . . . . .
H00P H 0.329355 0.279032 0.442659 0.046 Uiso 1 1 calc R . . . .
C00Q C 0.7864(3) 1.2744(3) 0.0675(2) 0.0479(6) Uani 1 1 d . . . . .
H00E H 0.690498 1.216661 0.010812 0.072 Uiso 1 1 calc GR . . . .
H00F H 0.855238 1.350136 0.035153 0.072 Uiso 1 1 calc GR . . . .
H00H H 0.766286 1.318256 0.142297 0.072 Uiso 1 1 calc GR . . . .
C00R C 1.0090(3) 1.2193(3) 0.0687(2) 0.0491(6) Uani 1 1 d . . . . .
H00J H 1.078480 1.257611 0.145106 0.074 Uiso 1 1 calc GR . . . .
H00K H 1.038653 1.292013 0.023960 0.074 Uiso 1 1 calc GR . . . .
H00Q H 1.013773 1.133081 0.023596 0.074 Uiso 1 1 calc GR . . . .
C00S C -0.1258(3) 0.5722(3) 0.4062(2) 0.0554(7) Uani 1 1 d . . . . .
H00R H -0.147407 0.607720 0.339785 0.083 Uiso 1 1 calc GR . . . .
H00S H -0.196222 0.572557 0.460749 0.083 Uiso 1 1 calc GR . . . .
H00T H -0.138497 0.473906 0.376092 0.083 Uiso 1 1 calc GR . . . .
C00T C 0.0508(3) 0.7712(3) 0.5752(2) 0.0654(8) Uani 1 1 d . . . . .
H00U H 0.127750 0.774942 0.635570 0.098 Uiso 1 1 calc GR . . . .
H00V H -0.045407 0.746138 0.604193 0.098 Uiso 1 1 calc GR . . . .
H00W H 0.084744 0.865331 0.558611 0.098 Uiso 1 1 calc GR . . . .
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
C00J N003 C00Q 120.32(19) . . ?
C00J N003 C00R 120.3(2) . . ?
C00R N003 C00Q 119.24(19) . . ?
C00F N004 C00S 120.4(2) . . ?
C00F N004 C00T 120.7(2) . . ?
C00T N004 C00S 117.2(2) . . ?
C006 C005 C008 120.23(18) . . ?
C006 C005 C00E 122.77(18) . . ?
C00E C005 C008 116.66(17) . . ?
C005 C006 C007 120.50(18) . . ?
C005 C006 C00K 126.57(18) . . ?
C007 C006 C00K 112.86(17) . . ?
N002 C007 C006 175.6(2) . . ?
C00B C008 C005 122.47(18) . . ?
C00C C008 C005 120.01(18) . . ?
C00C C008 C00B 117.46(19) . . ?
C00N C009 C00E 122.0(2) . . ?
C00H C00A C00I 119.08(19) . . ?
C00L C00B C008 121.6(2) . . ?
C00M C00C C008 121.61(19) . . ?
C00G C00D C00E 121.88(19) . . ?
C009 C00E C005 124.06(19) . . ?
C00D C00E C005 119.30(18) . . ?
C00D C00E C009 116.58(19) . . ?
N004 C00F C00L 121.9(2) . . ?
N004 C00F C00M 121.4(2) . . ?
C00M C00F C00L 116.70(19) . . ?
C00D C00G C00J 121.0(2) . . ?
C00A C00H Br01 119.50(16) . . ?
C00A C00H C00P 121.03(19) . . ?
C00P C00H Br01 119.45(16) . . ?
C00A C00I C00K 121.53(19) . . ?
N003 C00J C00G 121.5(2) . . ?
N003 C00J C00N 121.29(19) . . ?
C00G C00J C00N 117.22(19) . . ?
C00I C00K C006 120.51(18) . . ?
C00O C00K C006 121.94(19) . . ?
C00O C00K C00I 117.52(19) . . ?
C00B C00L C00F 121.25(19) . . ?
C00C C00M C00F 121.3(2) . . ?
C009 C00N C00J 120.95(19) . . ?
C00P C00O C00K 121.5(2) . . ?
C00O C00P C00H 119.4(2) . . ?
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
Br01 C00H 1.898(2) . ?
N002 C007 1.143(3) . ?
N003 C00J 1.370(3) . ?
N003 C00Q 1.452(3) . ?
N003 C00R 1.441(3) . ?
N004 C00F 1.373(3) . ?
N004 C00S 1.450(3) . ?
N004 C00T 1.440(3) . ?
C005 C006 1.370(3) . ?
C005 C008 1.483(3) . ?
C005 C00E 1.472(3) . ?
C006 C007 1.445(3) . ?
C006 C00K 1.486(3) . ?
C008 C00B 1.395(3) . ?
C008 C00C 1.391(3) . ?
C009 C00E 1.402(3) . ?
C009 C00N 1.379(3) . ?
C00A C00H 1.382(3) . ?
C00A C00I 1.383(3) . ?
C00B C00L 1.377(3) . ?
C00C C00M 1.377(3) . ?
C00D C00E 1.400(3) . ?
C00D C00G 1.382(3) . ?
C00F C00L 1.409(3) . ?
C00F C00M 1.407(3) . ?
C00G C00J 1.405(3) . ?
C00H C00P 1.383(3) . ?
C00I C00K 1.403(3) . ?
C00J C00N 1.406(3) . ?
C00K C00O 1.397(3) . ?
C00O C00P 1.381(3) . ?
