#------------------------------------------------------------------------------
#$Date: 2023-07-05 12:54:53 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284908 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/91/1569191.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_1569191
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         '0.095(C28 H20 N2 O2)'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2f4wvb
_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                 95.536(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9476(2)
_cell_length_b                   5.84090(10)
_cell_length_c                   15.0139(3)
_cell_measurement_reflns_used    5283
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      75.2710
_cell_measurement_theta_min      4.5300
_cell_volume                     1042.85(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.972
_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  0.0465
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9565
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.870
_diffrn_reflns_theta_min         4.523
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0395
_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)+(0.0486P)²+0.3923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1892
_reflns_number_total             2170
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc01730c2.cif
_cod_data_source_block           erbenan-1
_cod_depositor_comments
'Adding full bibliography for 1569190--1569193.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569191
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.51364(10) -0.0712(2) 0.43719(8) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.57531(10) 0.0830(2) 0.50167(8) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.71195(10) 0.3616(2) 0.56502(8) 0.0197(3) Uani 1 1 d . . . . .
C4 C 0.63680(10) 0.5197(2) 0.59437(8) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.559315 0.512703 0.573261 0.026 Uiso 1 1 calc R U . . .
C5 C 0.67598(11) 0.6884(2) 0.65490(8) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.624902 0.796427 0.675498 0.029 Uiso 1 1 calc R U . . .
C6 C 0.78934(12) 0.7000(2) 0.68543(9) 0.0261(3) Uani 1 1 d . . . . .
H6 H 0.815859 0.816001 0.726516 0.031 Uiso 1 1 calc R U . . .
C7 C 0.86355(11) 0.5414(2) 0.65570(9) 0.0268(3) Uani 1 1 d . . . . .
H7 H 0.941029 0.548977 0.676787 0.032 Uiso 1 1 calc R U . . .
C8 C 0.82590(11) 0.3720(2) 0.59549(9) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.877187 0.264011 0.575167 0.028 Uiso 1 1 calc R U . . .
C9 C 0.74926(10) 0.1227(2) 0.43543(8) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.76810(11) 0.2779(2) 0.36900(9) 0.0246(3) Uani 1 1 d . . . . .
H10 H 0.730753 0.421659 0.366026 0.030 Uiso 1 1 calc R U . . .
C11 C 0.84210(11) 0.2216(3) 0.30669(9) 0.0296(3) Uani 1 1 d . . . . .
H11 H 0.854898 0.325823 0.260174 0.036 Uiso 1 1 calc R U . . .
C12 C 0.89742(11) 0.0121(3) 0.31262(10) 0.0319(3) Uani 1 1 d . . . . .
H12 H 0.949455 -0.025490 0.270872 0.038 Uiso 1 1 calc R U . . .
C13 C 0.87694(12) -0.1421(3) 0.37915(10) 0.0308(3) Uani 1 1 d . . . . .
H13 H 0.914345 -0.285780 0.382298 0.037 Uiso 1 1 calc R U . . .
C14 C 0.80227(11) -0.0885(2) 0.44129(9) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.787789 -0.194359 0.486841 0.030 Uiso 1 1 calc R U . . .
N1 N 0.67450(8) 0.18709(18) 0.50186(7) 0.0193(2) Uani 1 1 d . . . . .
O1 O 0.52923(8) -0.14999(17) 0.36385(6) 0.0258(2) 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
C2 C1 C2 87.95(10) . 3_656 ?
O1 C1 C2 135.56(11) . . ?
O1 C1 C2 136.47(12) . 3_656 ?
C1 C2 C1 92.05(10) . 3_656 ?
N1 C2 C1 135.76(12) . 3_656 ?
N1 C2 C1 132.18(11) . . ?
C4 C3 C8 120.47(12) . . ?
C4 C3 N1 120.81(11) . . ?
C8 C3 N1 118.71(11) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.42(12) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.41(12) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.68(12) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.66(12) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 120.3 . . ?
C7 C8 C3 119.35(12) . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C14 121.62(12) . . ?
C10 C9 N1 118.70(11) . . ?
C14 C9 N1 119.66(11) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.34(13) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.72(13) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.19(12) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.58(14) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 118.52(13) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C2 N1 C3 123.14(10) . . ?
C2 N1 C9 119.15(10) . . ?
C3 N1 C9 117.71(10) . . ?
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 C2 1.4676(17) . ?
C1 C2 1.4714(16) 3_656 ?
C1 O1 1.2243(15) . ?
C2 N1 1.3315(16) . ?
C3 C4 1.3893(18) . ?
C3 C8 1.3951(17) . ?
C3 N1 1.4340(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3907(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3890(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3858(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3821(18) . ?
C9 C14 1.3861(18) . ?
C9 N1 1.4510(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3871(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.3873(18) . ?
C14 H14 0.9500 . ?
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
C1 C2 N1 C3 169.54(12) . . . . ?
C1 C2 N1 C3 -11.4(2) 3_656 . . . ?
C1 C2 N1 C9 168.52(13) 3_656 . . . ?
C1 C2 N1 C9 -10.5(2) . . . . ?
C2 C1 C2 C1 0.0 3_656 . . 3_656 ?
C2 C1 C2 N1 179.31(17) 3_656 . . . ?
C3 C4 C5 C6 0.41(19) . . . . ?
C4 C3 C8 C7 0.23(19) . . . . ?
C4 C3 N1 C2 -36.49(17) . . . . ?
C4 C3 N1 C9 143.54(12) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C8 C3 C4 C5 -0.34(18) . . . . ?
C8 C3 N1 C2 144.54(12) . . . . ?
C8 C3 N1 C9 -35.43(16) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C10 C9 C14 C13 0.8(2) . . . . ?
C10 C9 N1 C2 110.70(13) . . . . ?
C10 C9 N1 C3 -69.33(15) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C12 C13 C14 C9 -0.3(2) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
C14 C9 N1 C2 -71.08(16) . . . . ?
C14 C9 N1 C3 108.90(13) . . . . ?
N1 C3 C4 C5 -179.29(11) . . . . ?
N1 C3 C8 C7 179.21(11) . . . . ?
N1 C9 C10 C11 177.99(11) . . . . ?
N1 C9 C14 C13 -177.35(11) . . . . ?
O1 C1 C2 C1 178.57(19) . . . 3_656 ?
O1 C1 C2 N1 -2.1(3) . . . . ?
