#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:54:53 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/91/1569190.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_1569190
loop_
_publ_author_name
'Guo, Weihan'
'Wang, Mingda'
'Si, Leilei'
'Wang, Yigang'
'Xia, Guomin'
'Wang, Hongming'
_publ_section_title
;
 Precise peripheral design enables propeller-like squaraine dye with
 highly sensitive and wide-range piezochromism.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              6348
_journal_page_last               6354
_journal_paper_doi               10.1039/d3sc01730c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         '0.08(C32 H28 N2 O6)'
_chemical_formula_sum            'C32 H28 N2 O6'
_chemical_formula_weight         536.56
_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_block_doi                 10.5517/ccdc.csd.cc2f4wt9
_audit_creation_date             2023-01-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-31 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.013(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8624(4)
_cell_length_b                   4.0641(2)
_cell_length_c                   26.0523(9)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      75.4390
_cell_measurement_theta_min      75.4390
_cell_volume                     1252.90(9)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5898
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.704
_diffrn_reflns_theta_min         3.401
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0445
_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)+(0.0697P)²+0.3246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2099
_reflns_number_total             2601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01730c2.cif
_cod_data_source_block           jiayangji-1
_cod_depositor_comments
'Adding full bibliography for 1569190--1569193.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1569190
_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.
;
_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:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_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
C1 C -0.09592(12) 0.7339(5) 0.58066(6) 0.0289(4) Uani 1 1 d . . . . .
H1A H -0.092932 0.631441 0.546730 0.043 Uiso 1 1 calc R U . . .
H1B H -0.074599 0.966207 0.578569 0.043 Uiso 1 1 calc R U . . .
H1C H -0.172830 0.717014 0.591914 0.043 Uiso 1 1 calc R U . . .
C2 C 0.09201(12) 0.5583(4) 0.60608(6) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.13612(12) 0.7122(4) 0.56407(6) 0.0232(3) Uani 1 1 d . . . . .
H3 H 0.087696 0.828332 0.539769 0.028 Uiso 1 1 calc R U . . .
C4 C 0.25162(12) 0.6945(4) 0.55795(5) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.282347 0.804924 0.529976 0.026 Uiso 1 1 calc R U . . .
C5 C 0.32205(12) 0.5168(4) 0.59242(5) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.27729(12) 0.3595(4) 0.63412(6) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.325281 0.237325 0.657806 0.027 Uiso 1 1 calc R U . . .
C7 C 0.16335(12) 0.3821(4) 0.64079(6) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.133169 0.276441 0.669334 0.027 Uiso 1 1 calc R U . . .
C8 C 0.47444(12) 0.5000(4) 0.53654(6) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.42298(12) 0.3886(4) 0.48674(5) 0.0212(3) Uani 1 1 d . . . . .
C10 C 0.52527(12) 0.4876(4) 0.62715(6) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.62390(12) 0.3116(4) 0.62118(6) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.633262 0.196971 0.589984 0.027 Uiso 1 1 calc R U . . .
C12 C 0.70898(12) 0.3028(4) 0.66068(6) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.777238 0.187471 0.656151 0.027 Uiso 1 1 calc R U . . .
C13 C 0.69385(12) 0.4628(4) 0.70672(6) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.59387(12) 0.6337(4) 0.71319(6) 0.0222(3) Uani 1 1 d . . . . .
H14 H 0.583280 0.740394 0.744941 0.027 Uiso 1 1 calc R U . . .
C15 C 0.51010(12) 0.6486(4) 0.67359(6) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.442528 0.767798 0.677916 0.026 Uiso 1 1 calc R U . . .
C16 C 0.87415(13) 0.2899(4) 0.74256(6) 0.0271(4) Uani 1 1 d . . . . .
H16A H 0.912355 0.380714 0.713565 0.041 Uiso 1 1 calc R U . . .
H16B H 0.856851 0.057127 0.736080 0.041 Uiso 1 1 calc R U . . .
H16C H 0.923558 0.310566 0.774153 0.041 Uiso 1 1 calc R U . . .
N1 N 0.44073(10) 0.5004(3) 0.58483(5) 0.0214(3) Uani 1 1 d . . . . .
O1 O -0.01915(9) 0.5689(3) 0.61682(4) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.33498(8) 0.2504(3) 0.47161(4) 0.0238(3) Uani 1 1 d . . . . .
O3 O 0.77183(9) 0.4662(3) 0.74823(4) 0.0255(3) 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C7 C2 C3 119.75(13) . . ?
O1 C2 C3 124.53(14) . . ?
O1 C2 C7 115.72(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.55(14) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.41(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.84(13) . . ?
C4 C5 N1 119.15(13) . . ?
C6 C5 N1 121.01(14) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.83(14) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.60(14) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C8 45.97(8) 3_666 3_666 ?
C9 C8 C8 46.07(8) . 3_666 ?
C9 C8 C9 92.04(12) . 3_666 ?
N1 C8 C8 179.9(2) . 3_666 ?
N1 C8 C9 134.00(14) . . ?
N1 C8 C9 133.96(14) . 3_666 ?
C8 C9 C8 87.96(12) . 3_666 ?
O2 C9 C8 136.06(14) . 3_666 ?
O2 C9 C8 135.92(14) . . ?
C11 C10 C15 119.89(14) . . ?
C11 C10 N1 118.70(13) . . ?
C15 C10 N1 121.41(13) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.25(14) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.78(14) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.04(14) . . ?
O3 C13 C12 124.39(13) . . ?
O3 C13 C14 115.57(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.29(14) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.73(14) . . ?
C14 C15 H15 120.1 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
C5 N1 C10 122.24(12) . . ?
C8 N1 C5 119.11(12) . . ?
C8 N1 C10 118.65(12) . . ?
C2 O1 C1 117.29(12) . . ?
C13 O3 C16 116.42(12) . . ?
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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 O1 1.4305(19) . ?
C2 C3 1.394(2) . ?
C2 C7 1.393(2) . ?
C2 O1 1.3676(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 C6 1.397(2) . ?
C5 N1 1.4368(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C8 2.038(3) 3_666 ?
C8 C9 1.466(2) . ?
C8 C9 1.4687(19) 3_666 ?
C8 N1 1.3465(19) . ?
C9 O2 1.2258(19) . ?
C10 C11 1.389(2) . ?
C10 C15 1.398(2) . ?
C10 N1 1.4386(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C13 C14 1.395(2) . ?
C13 O3 1.3730(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 O3 1.4259(18) . ?
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
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C3 C2 O1 C1 3.7(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C3 C4 C5 N1 179.41(14) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C4 C5 N1 C8 -33.5(2) . . . . ?
C4 C5 N1 C10 145.94(15) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C6 C5 N1 C8 147.16(15) . . . . ?
C6 C5 N1 C10 -33.4(2) . . . . ?
C7 C2 C3 C4 -1.5(2) . . . . ?
C7 C2 O1 C1 -176.98(14) . . . . ?
C8 C8 C9 O2 177.3(2) 3_666 . . . ?
C9 C8 C9 C8 0.001(0) 3_666 . . 3_666 ?
C9 C8 C9 O2 177.3(2) 3_666 . . . ?
C9 C8 N1 C5 151.54(17) 3_666 . . . ?
C9 C8 N1 C5 -28.3(3) . . . . ?
C9 C8 N1 C10 152.25(17) . . . . ?
C9 C8 N1 C10 -27.9(3) 3_666 . . . ?
C10 C11 C12 C13 1.8(2) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
C11 C10 N1 C5 147.27(15) . . . . ?
C11 C10 N1 C8 -33.3(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C11 C12 C13 O3 179.25(14) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C12 C13 O3 C16 -0.3(2) . . . . ?
C13 C14 C15 C10 0.9(2) . . . . ?
C14 C13 O3 C16 179.36(14) . . . . ?
C15 C10 C11 C12 -1.8(2) . . . . ?
C15 C10 N1 C5 -33.0(2) . . . . ?
C15 C10 N1 C8 146.40(15) . . . . ?
N1 C5 C6 C7 179.32(14) . . . . ?
N1 C8 C9 C8 179.9(2) . . . 3_666 ?
N1 C8 C9 O2 -2.8(3) . . . . ?
N1 C10 C11 C12 177.92(13) . . . . ?
N1 C10 C15 C14 -179.25(14) . . . . ?
O1 C2 C3 C4 177.71(15) . . . . ?
O1 C2 C7 C6 -179.03(14) . . . . ?
O3 C13 C14 C15 179.38(13) . . . . ?
