#------------------------------------------------------------------------------
#$Date: 2022-02-04 22:05:47 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/46/1564687.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_1564687
loop_
_publ_author_name
'Fan, Yunhao'
'Han, Mengmeng'
'Huang, Arui'
'Liao, Qiuyan'
'Tu, Jin'
'Liu, Xiuxing'
'Huang, Bohan'
'Li, Qianqian'
'Li, Zhen'
_publ_section_title
;
 Multi-photoresponsive triphenylethylene derivatives with photochromism,
 photodeformation and room temperature phosphorescence.
;
_journal_issue                   1
_journal_name_full               'Materials horizons'
_journal_page_first              368
_journal_page_last               375
_journal_paper_doi               10.1039/d1mh01207j
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         'C21 H16 Br2'
_chemical_formula_sum            'C21 H16 Br2'
_chemical_formula_weight         428.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-06 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 121.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.880(9)
_cell_length_b                   8.745(6)
_cell_length_c                   18.874(10)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.22
_cell_volume                     1815(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1783
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9888
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        23.998
_diffrn_reflns_theta_max         23.998
_diffrn_reflns_theta_min         1.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.464
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.1919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.733
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.1325
_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)+(0.1158P)²+17.0489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2379
_refine_ls_wR_factor_ref         0.2764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1561
_reflns_number_total             2773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1mh01207j2.cif
_cod_data_source_block           mo_201115c_0m
_cod_depositor_comments
'Adding full bibliography for 1564683--1564688.cif.'
_cod_database_code               1564687
_shelx_shelxl_version_number     2014/7
_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   0.664
_shelx_estimated_absorpt_t_min   0.348
_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. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.35610(12) 0.2681(2) 0.08674(11) 0.0708(8) Uani 1 1 d . . . . .
Br2 Br 1.26010(13) 0.2995(2) 0.29301(12) 0.0598(7) Uani 1 1 d . . . . .
C1 C 0.5171(9) 0.2617(14) 0.1807(8) 0.028(3) Uani 1 1 d . . . . .
C2 C 0.5536(10) 0.1391(15) 0.2299(8) 0.035(3) Uani 1 1 d . U . . .
H2 H 0.5014 0.0569 0.2186 0.042 Uiso 1 1 calc R . . . .
C3 C 0.6697(10) 0.1365(15) 0.2976(8) 0.030(3) Uani 1 1 d . . . . .
H3 H 0.6954 0.0510 0.3319 0.037 Uiso 1 1 calc R . . . .
C4 C 0.7494(9) 0.2552(14) 0.3165(8) 0.026(3) Uani 1 1 d . . . . .
C5 C 0.7081(10) 0.3795(15) 0.2623(8) 0.032(4) Uani 1 1 d . . . . .
H5 H 0.7606 0.4611 0.2728 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5922(11) 0.3852(16) 0.1936(8) 0.035(4) Uani 1 1 d . . . . .
H6 H 0.5656 0.4682 0.1575 0.042 Uiso 1 1 calc R . . . .
C7 C 0.8748(10) 0.2511(14) 0.3889(7) 0.025(3) Uani 1 1 d . . . . .
C8 C 0.9675(9) 0.2666(15) 0.3660(8) 0.028(3) Uani 1 1 d . . . . .
C9 C 0.9634(11) 0.1717(17) 0.3053(8) 0.039(4) Uani 1 1 d . . . . .
H9 H 0.9006 0.1009 0.2793 0.047 Uiso 1 1 calc R . . . .
C10 C 1.0490(11) 0.1785(16) 0.2821(9) 0.039(4) Uani 1 1 d . U . . .
H10 H 1.0442 0.1132 0.2417 0.046 Uiso 1 1 calc R . . . .
C11 C 1.1431(11) 0.2860(17) 0.3209(9) 0.042(4) Uani 1 1 d . . . . .
C12 C 1.1486(10) 0.3827(16) 0.3800(8) 0.036(4) Uani 1 1 d . . . . .
H12 H 1.2104 0.4550 0.4048 0.044 Uiso 1 1 calc R . . . .
C13 C 1.0625(10) 0.3734(16) 0.4029(7) 0.036(4) Uani 1 1 d . . . . .
H13 H 1.0679 0.4390 0.4434 0.043 Uiso 1 1 calc R . . . .
C14 C 0.8981(10) 0.2332(15) 0.4650(8) 0.034(4) Uani 1 1 d . . . . .
C15 C 0.8030(11) 0.2308(15) 0.4852(8) 0.032(3) Uani 1 1 d . . . . .
C16 C 0.7099(10) 0.3416(17) 0.4529(8) 0.036(4) Uani 1 1 d . . . . .
H16 H 0.7112 0.4189 0.4195 0.043 Uiso 1 1 calc R . . . .
C17 C 0.6186(13) 0.340(2) 0.4686(9) 0.057(5) Uani 1 1 d . . . . .
H17 H 0.5572 0.4128 0.4453 0.068 Uiso 1 1 calc R . . . .
C18 C 0.6185(17) 0.226(2) 0.5203(12) 0.069(5) Uani 1 1 d . U . . .
H18 H 0.5566 0.2215 0.5318 0.083 Uiso 1 1 calc R . . . .
C19 C 0.7094(18) 0.123(3) 0.5534(13) 0.087(6) Uani 1 1 d . U . . .
H19 H 0.7107 0.0490 0.5891 0.105 Uiso 1 1 calc R . . . .
C20 C 0.7996(16) 0.124(2) 0.5360(12) 0.064(5) Uani 1 1 d . . . . .
H20 H 0.8603 0.0506 0.5597 0.076 Uiso 1 1 calc R . . . .
C21 C 1.0266(13) 0.2110(18) 0.5425(9) 0.058(5) Uani 1 1 d . . . . .
H21A H 1.0825 0.1840 0.5254 0.088 Uiso 1 1 calc GR . . . .
H21B H 1.0243 0.1309 0.5764 0.088 Uiso 1 1 calc GR . . . .
H21C H 1.0526 0.3044 0.5737 0.088 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 0.0030 0.0020 '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 -0.2900 2.4600 '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
C2 C1 Br1 119.4(9) . . ?
C2 C1 C6 123.0(10) . . ?
C6 C1 Br1 117.6(10) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(11) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.5(12) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 116.8(11) . . ?
C3 C4 C7 122.3(12) . . ?
C5 C4 C7 120.9(10) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(11) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 116.9(12) . . ?
C5 C6 H6 121.5 . . ?
C8 C7 C4 113.0(11) . . ?
C14 C7 C4 122.0(11) . . ?
C14 C7 C8 125.0(10) . . ?
C9 C8 C7 119.8(11) . . ?
C9 C8 C13 117.0(12) . . ?
C13 C8 C7 123.2(12) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.6(12) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(14) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 Br2 120.5(12) . . ?
C12 C11 Br2 119.3(10) . . ?
C12 C11 C10 120.2(13) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(12) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(13) . . ?
C12 C13 H13 119.4 . . ?
C7 C14 C15 122.8(11) . . ?
C7 C14 C21 124.8(12) . . ?
C15 C14 C21 112.4(12) . . ?
C16 C15 C14 121.1(13) . . ?
C20 C15 C14 122.4(13) . . ?
C20 C15 C16 116.5(14) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.4(15) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.7(15) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(18) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 122(2) . . ?
C20 C19 H19 119.1 . . ?
C15 C20 C19 121.5(17) . . ?
C15 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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 1.902(11) . ?
Br2 C11 1.841(14) . ?
C1 C2 1.334(18) . ?
C1 C6 1.385(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(17) . ?
C4 C5 1.395(18) . ?
C4 C7 1.476(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.473(18) . ?
C7 C14 1.316(18) . ?
C8 C9 1.393(18) . ?
C8 C13 1.402(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.402(19) . ?
C11 C12 1.37(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.461(19) . ?
C14 C21 1.547(17) . ?
C15 C16 1.410(18) . ?
C15 C20 1.35(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.35(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.39(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.34(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.36(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
Br1 C1 C2 C3 -179.7(10) . . . . ?
Br1 C1 C6 C5 179.5(10) . . . . ?
Br2 C11 C12 C13 -179.1(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C1 C6 C5 -2(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C2 C3 C4 C7 -179.2(13) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C3 C4 C7 C8 120.6(14) . . . . ?
C3 C4 C7 C14 -58.6(19) . . . . ?
C4 C5 C6 C1 0(2) . . . . ?
C4 C7 C8 C9 -51.7(16) . . . . ?
C4 C7 C8 C13 128.7(13) . . . . ?
C4 C7 C14 C15 -6(2) . . . . ?
C4 C7 C14 C21 173.3(13) . . . . ?
C5 C4 C7 C8 -57.0(16) . . . . ?
C5 C4 C7 C14 123.9(15) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
C7 C4 C5 C6 179.0(13) . . . . ?
C7 C8 C9 C10 -178.7(12) . . . . ?
C7 C8 C13 C12 179.3(12) . . . . ?
C7 C14 C15 C16 -46.7(19) . . . . ?
C7 C14 C15 C20 133.9(16) . . . . ?
C8 C7 C14 C15 174.9(12) . . . . ?
C8 C7 C14 C21 -6(2) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
C9 C8 C13 C12 -0.4(19) . . . . ?
C9 C10 C11 Br2 179.7(10) . . . . ?
C9 C10 C11 C12 -1(2) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C12 C13 C8 -1(2) . . . . ?
C13 C8 C9 C10 1(2) . . . . ?
C14 C7 C8 C9 127.4(14) . . . . ?
C14 C7 C8 C13 -52.2(19) . . . . ?
C14 C15 C16 C17 178.0(13) . . . . ?
C14 C15 C20 C19 -179.3(16) . . . . ?
C15 C16 C17 C18 2(2) . . . . ?
C16 C15 C20 C19 1(2) . . . . ?
C16 C17 C18 C19 1(3) . . . . ?
C17 C18 C19 C20 -2(3) . . . . ?
C18 C19 C20 C15 1(3) . . . . ?
C20 C15 C16 C17 -3(2) . . . . ?
C21 C14 C15 C16 133.9(13) . . . . ?
C21 C14 C15 C20 -45.5(19) . . . . ?
