#------------------------------------------------------------------------------
#$Date: 2021-06-26 03:30:45 +0300 (Sat, 26 Jun 2021) $
#$Revision: 266703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518839.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_4518839
loop_
_publ_author_name
'Barman, Debasish'
'Gopikrishna, Peddaboodi'
'Iyer, Parameswar Krishnan'
_publ_section_title
;
 Stimuli-Responsive Trimorphs and Charge-Transfer Complexes of a Twisted
 Molecular Donor.
;
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_paper_doi               10.1021/acs.langmuir.1c01172
_journal_year                    2021
_chemical_formula_sum            'C23 H11 Cl4 O2'
_chemical_formula_weight         461.12
_chemical_melting_point          523
_chemical_name_systematic        DBFTCQ
_chemical_properties_physical    Heat-sensitive
_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-2018/3
_audit_update_record
;
2019-06-21 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.027(9)
_cell_angle_beta                 99.706(7)
_cell_angle_gamma                91.048(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3722(5)
_cell_length_b                   9.0690(10)
_cell_length_c                   14.8974(14)
_cell_measurement_reflns_used    1905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.685
_cell_measurement_theta_min      2.273
_cell_volume                     978.88(16)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.732
_diffrn_reflns_theta_min         2.252
_exptl_absorpt_coefficient_mu    0.623
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       sheet
_exptl_crystal_F_000             466
_exptl_crystal_preparation       Mechanochromism
_exptl_crystal_recrystallization_method 'Vapour deposition'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+0.0221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1753
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2520
_reflns_number_total             4404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            la1c01172_si_011.cif
_cod_data_source_block           TAHTCQ
_cod_database_code               4518839
_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.
;
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
Cl9 Cl 0.77938(14) 0.88169(12) 0.90621(8) 0.0670(4) Uani 1 1 d . . . . .
Cl8 Cl 0.61956(14) 0.92449(11) 0.69855(8) 0.0658(3) Uani 1 1 d . . . . .
Cl10 Cl 0.38211(14) 0.35169(12) 0.65243(8) 0.0690(4) Uani 1 1 d . . . . .
Cl7 Cl 0.53296(15) 0.31372(12) 0.86139(9) 0.0719(4) Uani 1 1 d . . . . .
O11 O 0.4588(4) 0.6492(3) 0.6037(2) 0.0701(9) Uani 1 1 d . . . . .
O12 O 0.7179(4) 0.5821(3) 0.9517(2) 0.0704(9) Uani 1 1 d . . . . .
C14 C -0.0360(4) 0.5255(4) 0.6843(2) 0.0349(8) Uani 1 1 d . . . . .
C16 C 0.1042(4) 0.7556(4) 0.7423(2) 0.0343(8) Uani 1 1 d . . . . .
C13 C 0.0426(4) 0.5140(4) 0.7763(2) 0.0361(8) Uani 1 1 d . . . . .
C21 C 0.1288(4) 0.6582(4) 0.8121(2) 0.0373(8) Uani 1 1 d . . . . .
C15 C -0.0012(4) 0.6768(4) 0.6582(2) 0.0352(8) Uani 1 1 d . . . . .
C27 C -0.0305(5) 0.8654(4) 0.5390(2) 0.0394(8) Uani 1 1 d . . . . .
C20 C 0.2204(4) 0.7021(4) 0.8994(2) 0.0417(8) Uani 1 1 d . . . . .
H20 H 0.238677 0.635484 0.944591 0.050 Uiso 1 1 calc R U . . .
C28 C 0.1467(5) 0.9275(4) 0.5448(2) 0.0407(8) Uani 1 1 d . . . . .
H28 H 0.246950 0.878667 0.574346 0.049 Uiso 1 1 calc R U . . .
C25 C 0.0286(5) 0.3823(4) 0.8172(3) 0.0436(9) Uani 1 1 d . . . . .
H25 H 0.077530 0.375499 0.878449 0.052 Uiso 1 1 calc R U . . .
C1 C 0.5588(4) 0.4741(4) 0.8118(3) 0.0440(9) Uani 1 1 d . . . . .
C22 C -0.1235(4) 0.4036(4) 0.6330(3) 0.0430(9) Uani 1 1 d . . . . .
H22 H -0.174695 0.409799 0.571975 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6725(4) 0.7412(4) 0.8331(3) 0.0416(8) Uani 1 1 d . . . . .
C26 C -0.0652(4) 0.7241(4) 0.5759(2) 0.0420(9) Uani 1 1 d . . . . .
H26 H -0.143104 0.657367 0.536459 0.050 Uiso 1 1 calc R U . . .
C17 C 0.1651(4) 0.9023(4) 0.7633(2) 0.0416(8) Uani 1 1 d . . . . .
H17 H 0.146517 0.970060 0.718879 0.050 Uiso 1 1 calc R U . . .
C5 C 0.5147(5) 0.6352(4) 0.6830(3) 0.0439(9) Uani 1 1 d . . . . .
C29 C 0.1762(5) 1.0586(4) 0.5080(2) 0.0413(8) Uani 1 1 d . . . . .
H29 H 0.295467 1.097858 0.514491 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6058(4) 0.7598(4) 0.7456(3) 0.0430(9) Uani 1 1 d . . . . .
C2 C 0.6558(5) 0.5975(4) 0.8735(3) 0.0447(9) Uani 1 1 d . . . . .
C18 C 0.2533(5) 0.9463(4) 0.8508(3) 0.0459(9) Uani 1 1 d . . . . .
H18 H 0.292833 1.044450 0.864852 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4941(4) 0.4913(4) 0.7239(3) 0.0444(9) Uani 1 1 d . . . . .
C23 C -0.1339(5) 0.2718(4) 0.6741(3) 0.0489(10) Uani 1 1 d . . . . .
H23 H -0.191662 0.189195 0.639808 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2838(5) 0.8471(4) 0.9176(3) 0.0477(9) Uani 1 1 d . . . . .
H19 H 0.347539 0.878277 0.975305 0.057 Uiso 1 1 calc R U . . .
C24 C -0.0602(5) 0.2608(4) 0.7648(3) 0.0488(9) Uani 1 1 d . . . . .
H24 H -0.069914 0.171503 0.790981 0.059 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C22 C14 C13 119.9(3) . . ?
C22 C14 C15 130.5(3) . . ?
C13 C14 C15 109.5(3) . . ?
C17 C16 C21 118.4(3) . . ?
C17 C16 C15 132.5(3) . . ?
C21 C16 C15 108.9(3) . . ?
C25 C13 C14 120.6(3) . . ?
C25 C13 C21 131.6(3) . . ?
C14 C13 C21 107.8(3) . . ?
C20 C21 C16 121.8(3) . . ?
C20 C21 C13 129.3(3) . . ?
C16 C21 C13 108.9(3) . . ?
C26 C15 C14 123.8(3) . . ?
C26 C15 C16 131.2(3) . . ?
C14 C15 C16 104.9(3) . . ?
C28 C27 C29 117.0(3) . 2_576 ?
C28 C27 C26 122.6(3) . . ?
C29 C27 C26 120.3(3) 2_576 . ?
C19 C20 C21 118.4(3) . . ?
C29 C28 C27 121.6(3) . . ?
C13 C25 C24 118.7(3) . . ?
C6 C1 C2 121.4(4) . . ?
C6 C1 Cl7 123.1(3) . . ?
C2 C1 Cl7 115.5(3) . . ?
C14 C22 C23 119.0(3) . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 Cl9 122.3(3) . . ?
C2 C3 Cl9 115.5(3) . . ?
C15 C26 C27 129.5(3) . . ?
C18 C17 C16 119.5(3) . . ?
O11 C5 C4 121.9(4) . . ?
O11 C5 C6 121.4(4) . . ?
C4 C5 C6 116.7(3) . . ?
C28 C29 C27 121.4(3) . 2_576 ?
C3 C4 C5 121.2(3) . . ?
C3 C4 Cl8 122.9(3) . . ?
C5 C4 Cl8 115.8(3) . . ?
O12 C2 C3 121.5(4) . . ?
O12 C2 C1 121.8(4) . . ?
C3 C2 C1 116.7(3) . . ?
C19 C18 C17 121.2(4) . . ?
C1 C6 C5 121.7(3) . . ?
C1 C6 Cl10 122.1(3) . . ?
C5 C6 Cl10 116.1(3) . . ?
C24 C23 C22 121.4(3) . . ?
C20 C19 C18 120.6(3) . . ?
C23 C24 C25 120.4(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
Cl9 C3 1.705(3) . ?
Cl8 C4 1.703(4) . ?
Cl10 C6 1.701(4) . ?
Cl7 C1 1.698(4) . ?
O11 C5 1.201(4) . ?
O12 C2 1.196(4) . ?
C14 C22 1.382(5) . ?
C14 C13 1.407(4) . ?
C14 C15 1.481(5) . ?
C16 C17 1.394(4) . ?
C16 C21 1.403(5) . ?
C16 C15 1.486(4) . ?
C13 C25 1.389(5) . ?
C13 C21 1.468(5) . ?
C21 C20 1.388(5) . ?
C15 C26 1.340(4) . ?
C27 C28 1.399(5) . ?
C27 C29 1.400(4) 2_576 ?
C27 C26 1.465(5) . ?
C20 C19 1.380(5) . ?
C28 C29 1.373(5) . ?
C25 C24 1.390(5) . ?
C1 C6 1.338(5) . ?
C1 C2 1.488(5) . ?
C22 C23 1.387(5) . ?
C3 C4 1.337(5) . ?
C3 C2 1.485(5) . ?
C17 C18 1.382(5) . ?
C5 C4 1.487(5) . ?
C5 C6 1.494(5) . ?
C18 C19 1.382(5) . ?
C23 C24 1.380(5) . ?
