Dual-colored 4,4′,4′′,4′′′-(cyclobutane-1,2,3,4-tetrayl)-tetrabenzoate electrochromic materials with large optical contrast and coloration efficiency
Zhu, Chun-rong; Xie, Jia-ping; Mou, Hong-rong; Huang, Zhen-jie; Tang, Qian; Gong, Cheng-bin; Fu, Xiang-kai; New Journal of Chemistry 43 (2019) 13654–; doi:10.1039/C9NJ03352A

data_7058717
_publ_section_title
;
 Dual-colored
 4,4&#x2032;,4&#x2032;&#x2032;,4&#x2032;&#x2032;&#x2032;-(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  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -91.00  -3.00   1.00    1.00    --  -37.03 126.00 -90.00   88
  2  \w    -54.00  30.00   1.00    1.00    --  -37.03  57.00  60.00   84
  3  \w   -107.00  -8.00   1.00    1.00    --  -37.03 -19.00-120.00   99
  4  \w    -91.00  -3.00   1.00    1.00    --  -37.03 126.00 150.00   88
  5  \w     20.00 104.00   1.00    1.00    --   37.03  57.00-150.00   84
  6  \w    -32.00  56.00   1.00    1.00    --   37.03 -38.00-120.00   88
  7  \w     10.00 105.00   1.00    1.00    --   37.03  77.00 -30.00   95
  8  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 150.00   67
  9  \w     18.00 106.00   1.00    1.00    --   37.03  38.00 150.00   88
 10  \w    -31.00  64.00   1.00    1.00    --   37.03 -77.00-150.00   95
 11  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 120.00   67
 12  \w     10.00 105.00   1.00    1.00    --   37.03  77.00-150.00   95
 13  \w     41.00 116.00   1.00    1.00    --  110.47-112.00  30.00   75
 14  \w     42.00 128.00   1.00    1.00    --  110.47 -45.00   0.00   86
 15  \w     44.00 129.00   1.00    1.00    --  110.47 -61.00 -60.00   85
 16  \w     44.00 129.00   1.00    1.00    --  110.47 -61.00-150.00   85
 17  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00-120.00   68
 18  \w     42.00 128.00   1.00    1.00    --  110.47 -45.00  90.00   86
 19  \w     84.00 178.00   1.00    1.00    --  110.47  77.00 150.00   94
 20  \w     93.00 178.00   1.00    1.00    --  110.47  45.00 120.00   85
 21  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00 150.00   68
 22  \w     42.00 128.00   1.00    1.00    --  110.47 -45.00-180.00   86
 23  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00 -90.00   68
 24  \w    101.00 178.00   1.00    1.00    --  110.47 112.00-120.00   77
 25  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00  90.00   68
 26  \w     41.00 178.00   1.00    1.00    --  110.47   0.00  90.00  137
 27  \w     20.00 104.00   1.00    1.00    --   37.03  57.00 -60.00   84
 28  \w     10.00 105.00   1.00    1.00    --   37.03  77.00 150.00   95
 29  \w     10.00 105.00   1.00    1.00    --   37.03  77.00  90.00   95
 30  \w     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       '\w 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/[\s^2^(Fo^2^)+(0.0960P)^2^+0.1590P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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'
_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