#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058717.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_7058717
loop_
_publ_author_name
'Zhu, Chun-rong'
'Xie, Jia-ping'
'Mou, Hong-rong'
'Huang, Zhen-jie'
'Tang, Qian'
'Gong, Cheng-bin'
'Fu, Xiang-kai'
_publ_section_title
;
 Dual-colored
 4,4′,4′′,4′′′-(cyclobutane-1,2,3,4-tetrayl)-tetrabenzoate
 electrochromic materials with large optical contrast and coloration
 efficiency
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13654
_journal_paper_doi               10.1039/C9NJ03352A
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C40 H40 O8'
_chemical_formula_sum            'C40 H40 O8'
_chemical_formula_weight         648.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-27 deposited with the CCDC.    2019-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                99.715(4)
_cell_angle_beta                 94.914(3)
_cell_angle_gamma                94.610(3)
_cell_formula_units_Z            1
_cell_length_a                   7.7762(2)
_cell_length_b                   8.2847(4)
_cell_length_c                   13.7706(6)
_cell_measurement_reflns_used    5637
_cell_measurement_temperature    292.0(2)
_cell_measurement_theta_max      72.7480
_cell_measurement_theta_min      5.4330
_cell_volume                     867.14(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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_environment      air
_diffrn_ambient_temperature      292.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00  -3.00   1.00    1.00    --  -37.03 126.00 -90.00   88
  2  ω    -54.00  30.00   1.00    1.00    --  -37.03  57.00  60.00   84
  3  ω   -107.00  -8.00   1.00    1.00    --  -37.03 -19.00-120.00   99
  4  ω    -91.00  -3.00   1.00    1.00    --  -37.03 126.00 150.00   88
  5  ω     20.00 104.00   1.00    1.00    --   37.03  57.00-150.00   84
  6  ω    -32.00  56.00   1.00    1.00    --   37.03 -38.00-120.00   88
  7  ω     10.00 105.00   1.00    1.00    --   37.03  77.00 -30.00   95
  8  ω     24.00  91.00   1.00    1.00    --   37.03-126.00 150.00   67
  9  ω     18.00 106.00   1.00    1.00    --   37.03  38.00 150.00   88
 10  ω    -31.00  64.00   1.00    1.00    --   37.03 -77.00-150.00   95
 11  ω     24.00  91.00   1.00    1.00    --   37.03-126.00 120.00   67
 12  ω     10.00 105.00   1.00    1.00    --   37.03  77.00-150.00   95
 13  ω     41.00 116.00   1.00    1.00    --  110.47-112.00  30.00   75
 14  ω     42.00 128.00   1.00    1.00    --  110.47 -45.00   0.00   86
 15  ω     44.00 129.00   1.00    1.00    --  110.47 -61.00 -60.00   85
 16  ω     44.00 129.00   1.00    1.00    --  110.47 -61.00-150.00   85
 17  ω     41.00 109.00   1.00    1.00    --  110.47 -95.00-120.00   68
 18  ω     42.00 128.00   1.00    1.00    --  110.47 -45.00  90.00   86
 19  ω     84.00 178.00   1.00    1.00    --  110.47  77.00 150.00   94
 20  ω     93.00 178.00   1.00    1.00    --  110.47  45.00 120.00   85
 21  ω     41.00 109.00   1.00    1.00    --  110.47 -95.00 150.00   68
 22  ω     42.00 128.00   1.00    1.00    --  110.47 -45.00-180.00   86
 23  ω     41.00 109.00   1.00    1.00    --  110.47 -95.00 -90.00   68
 24  ω    101.00 178.00   1.00    1.00    --  110.47 112.00-120.00   77
 25  ω     41.00 109.00   1.00    1.00    --  110.47 -95.00  90.00   68
 26  ω     41.00 178.00   1.00    1.00    --  110.47   0.00  90.00  137
 27  ω     20.00 104.00   1.00    1.00    --   37.03  57.00 -60.00   84
 28  ω     10.00 105.00   1.00    1.00    --   37.03  77.00 150.00   95
 29  ω     10.00 105.00   1.00    1.00    --   37.03  77.00  90.00   95
 30  ω     20.00 104.00   1.00    1.00    --   37.03  57.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0439267000
_diffrn_orient_matrix_UB_12      -0.1209438000
_diffrn_orient_matrix_UB_13      0.0699645000
_diffrn_orient_matrix_UB_21      -0.0192321000
_diffrn_orient_matrix_UB_22      0.1332795000
_diffrn_orient_matrix_UB_23      0.0899762000
_diffrn_orient_matrix_UB_31      -0.1939373000
_diffrn_orient_matrix_UB_32      -0.0594655000
_diffrn_orient_matrix_UB_33      -0.0049448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.030
_diffrn_reflns_theta_min         5.443
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046
_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     239
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0580
_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)+(0.0960P)²+0.1590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3008
_reflns_number_total             3389
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj03352a2.cif
_cod_data_source_block           exp_1882
_cod_depositor_comments          'Adding full bibliography for 7058717.cif.'
_cod_database_code               7058717
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C1 H1 N1'
_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.
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C19 \\sim C18A-C19A
 with sigma of 0.004
3. Uiso/Uaniso restraints and constraints
C18A \\sim C18 \\sim C19 \\sim C19A: within 1.7A with sigma of 0.004 and sigma
for terminal atoms of 0.008
4. Others
 Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C18A(H18C,H18D)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_olex2_date_sample_data_collection 2018-11-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.498
_oxdiff_exptl_absorpt_empirical_full_min 0.460
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
O1 O 0.39124(18) 0.23509(15) 0.37870(12) 0.0751(4) Uani 1 1 d . . . . .
O2 O 0.23481(19) 1.45565(19) 0.98881(9) 0.0742(4) Uani 1 1 d . . . . .
O3 O 0.5494(2) 0.38010(17) 0.28890(11) 0.0751(4) Uani 1 1 d . . . . .
C C 0.21208(17) 0.80736(17) 0.46500(10) 0.0400(3) Uani 1 1 d . . . . .
C1 C 0.13392(17) 0.96459(17) 0.50115(10) 0.0399(3) Uani 1 1 d . . . . .
H1 H 0.227546 1.049982 0.529875 0.048 Uiso 1 1 calc R . . . .
C2 C 0.03680(18) 1.05701(18) 0.67760(10) 0.0417(3) Uani 1 1 d . . . . .
C3 C -0.00826(18) 0.96420(17) 0.57394(10) 0.0401(3) Uani 1 1 d . . . . .
H3 H -0.050950 0.850416 0.576081 0.048 Uiso 1 1 calc R . . . .
O8 O 0.1199(3) 1.2443(3) 1.04757(11) 0.1208(8) Uani 1 1 d . . . . .
C4 C 0.3301(2) 0.80760(19) 0.39419(12) 0.0494(4) Uani 1 1 d . . . . .
H4 H 0.359860 0.904476 0.371303 0.059 Uiso 1 1 calc R . . . .
C5 C 0.4327(2) 0.3626(2) 0.35328(13) 0.0540(4) Uani 1 1 d . . . . .
C6 C 0.17556(19) 0.66258(19) 0.49976(12) 0.0495(4) Uani 1 1 d . . . . .
H6 H 0.099714 0.660305 0.548292 0.059 Uiso 1 1 calc R . . . .
C7 C -0.0102(2) 0.9861(2) 0.75670(12) 0.0520(4) Uani 1 1 d . . . . .
H7 H -0.070351 0.881881 0.744657 0.062 Uiso 1 1 calc R . . . .
C8 C 0.36186(18) 0.52066(18) 0.39111(12) 0.0460(4) Uani 1 1 d . . . . .
C9 C 0.1255(2) 1.2134(2) 0.69837(11) 0.0507(4) Uani 1 1 d . . . . .
H9 H 0.158210 1.263767 0.646438 0.061 Uiso 1 1 calc R . . . .
C10 C 0.1186(2) 1.2226(2) 0.87315(12) 0.0548(4) Uani 1 1 d . . . . .
C11 C 0.4037(2) 0.6662(2) 0.35748(12) 0.0512(4) Uani 1 1 d . . . . .
H11 H 0.481559 0.668649 0.310004 0.061 Uiso 1 1 calc R . . . .
C12 C 0.2497(2) 0.52087(19) 0.46376(13) 0.0517(4) Uani 1 1 d . . . . .
H12 H 0.223776 0.425133 0.488634 0.062 Uiso 1 1 calc R . . . .
C13 C 0.1661(2) 1.2957(2) 0.79490(12) 0.0545(4) Uani 1 1 d . . . . .
H13 H 0.225394 1.400306 0.807174 0.065 Uiso 1 1 calc R . . . .
C14 C 0.0304(2) 1.0670(2) 0.85321(13) 0.0622(5) Uani 1 1 d . . . . .
H14 H -0.001790 1.016532 0.905173 0.075 Uiso 1 1 calc R . . . .
C15 C 0.1564(3) 1.3060(3) 0.97865(14) 0.0690(5) Uani 1 1 d . . . . .
C16 C 0.2719(4) 1.5453(3) 1.08999(15) 0.0881(7) Uani 1 1 d . . . . .
H16A H 0.353282 1.490392 1.127309 0.106 Uiso 1 1 calc R . . . .
H16B H 0.166191 1.550339 1.122552 0.106 Uiso 1 1 calc R . . . .
C17 C 0.3470(4) 1.7129(3) 1.08502(19) 0.1005(8) Uani 1 1 d . . . . .
H17A H 0.268468 1.763518 1.044488 0.151 Uiso 1 1 calc GR . . . .
H17B H 0.455461 1.706888 1.056824 0.151 Uiso 1 1 calc GR . . . .
H17C H 0.365696 1.777237 1.150521 0.151 Uiso 1 1 calc GR . . . .
C18 C 0.6374(6) 0.2397(5) 0.2479(3) 0.0817(11) Uani 0.748(6) 1 d D U P A 1
H18A H 0.660314 0.172636 0.297991 0.098 Uiso 0.748(6) 1 calc R . P A 1
H18B H 0.747406 0.277576 0.227160 0.098 Uiso 0.748(6) 1 calc R . P A 1
C19 C 0.5269(7) 0.1405(5) 0.1618(3) 0.1149(15) Uani 0.748(6) 1 d D U P A 1
H19A H 0.498531 0.209148 0.114294 0.172 Uiso 0.748(6) 1 calc GR . P A 1
H19B H 0.422233 0.095773 0.183679 0.172 Uiso 0.748(6) 1 calc GR . P A 1
H19C H 0.588507 0.052370 0.131807 0.172 Uiso 0.748(6) 1 calc GR . P A 1
C19A C 0.648(2) 0.2217(15) 0.1535(8) 0.100(2) Uani 0.252(6) 1 d D U P A 2
H19D H 0.566622 0.271962 0.114539 0.149 Uiso 0.252(6) 1 calc GR . P A 2
H19E H 0.668984 0.116985 0.117003 0.149 Uiso 0.252(6) 1 calc GR . P A 2
H19F H 0.754951 0.291515 0.168481 0.149 Uiso 0.252(6) 1 calc GR . P A 2
C18A C 0.576(2) 0.198(2) 0.2470(10) 0.092(2) Uani 0.252(6) 1 d D U P A 2
H18C H 0.657759 0.153429 0.290230 0.110 Uiso 0.252(6) 1 calc R . P A 2
H18D H 0.467657 0.127997 0.234857 0.110 Uiso 0.252(6) 1 calc R . P A 2
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'
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_3
C15 O2 C16 116.00(17) .
C5 O3 C18 119.8(2) .
C5 O3 C18A 102.2(4) .
C4 C C1 118.76(12) .
C6 C C1 123.41(13) .
C6 C C4 117.82(13) .
C C1 C3 119.70(11) .
C C1 C3 118.70(11) 2_576
C3 C1 C3 90.47(10) 2_576
C7 C2 C3 119.61(13) .
C7 C2 C9 117.76(14) .
C9 C2 C3 122.62(12) .
C1 C3 C1 89.53(10) 2_576
C2 C3 C1 117.71(11) .
C2 C3 C1 119.79(11) 2_576
C11 C4 C 121.10(14) .
O1 C5 O3 123.90(16) .
O1 C5 C8 123.70(17) .
O3 C5 C8 112.39(14) .
C C6 C12 121.31(14) .
C14 C7 C2 121.29(15) .
C11 C8 C5 123.35(15) .
C12 C8 C5 117.78(14) .
C12 C8 C11 118.87(14) .
C13 C9 C2 121.31(14) .
C13 C10 C15 122.62(17) .
C14 C10 C13 118.97(16) .
C14 C10 C15 118.41(16) .
C4 C11 C8 120.34(15) .
C8 C12 C6 120.49(14) .
C10 C13 C9 120.14(16) .
C7 C14 C10 120.53(15) .
O2 C15 C10 113.26(16) .
O8 C15 O2 122.82(19) .
O8 C15 C10 123.9(2) .
O2 C16 C17 107.61(19) .
O3 C18 C19 109.5(3) .
C19A C18A O3 99.2(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.197(2) .
O2 C15 1.317(3) .
O2 C16 1.457(2) .
O3 C5 1.338(2) .
O3 C18 1.453(4) .
O3 C18A 1.559(16) .
C C1 1.5080(19) .
C C4 1.395(2) .
C C6 1.382(2) .
C1 C3 1.5548(18) .
C1 C3 1.5803(19) 2_576
C2 C3 1.5007(19) .
C2 C7 1.384(2) .
C2 C9 1.391(2) .
O8 C15 1.195(2) .
C4 C11 1.383(2) .
C5 C8 1.491(2) .
C6 C12 1.385(2) .
C7 C14 1.382(2) .
C8 C11 1.387(2) .
C8 C12 1.382(2) .
C9 C13 1.385(2) .
C10 C13 1.385(2) .
C10 C14 1.383(3) .
C10 C15 1.493(2) .
C16 C17 1.477(4) .
C18 C19 1.484(5) .
C19A C18A 1.482(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102044909
