Effects of different types of unsymmetrical squaraines on the material properties and Coulomb interactions in organic photovoltaic devices
Yang, Lin; Yang, Daobin; Chen, Yao; Wu, Jianglin; Lu, Zhiyun; Sasabe, Hisahiro; Kido, Junji; Sano, Takeshi; Huang, Yan; Materials Chemistry Frontiers 2 (2018) 2116–; doi:10.1039/C8QM00327K

data_1554226
_publ_section_title
;
 Effects of different types of unsymmetrical squaraines on the material
 properties and Coulomb interactions in organic photovoltaic devices
;
_journal_issue                   11
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              2116
_journal_paper_doi               10.1039/C8QM00327K
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C30 H22 N2 O4, C0.5 Cl'
_chemical_formula_sum            'C30.5 H23 Cl N2 O4'
_chemical_formula_weight         516.96
_chemical_melting_point          523.5(5)
_chemical_name_systematic
2-(2,6-dihydroxy-4-(indolin-1-yl)phenyl)-4-(diphenylamino)cyclobuta-1,3-diene-1,3-bis(olate)
_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     direct
_audit_creation_date             2015-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-06-25 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.264(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8232(8)
_cell_length_b                   14.4169(9)
_cell_length_c                   14.7764(9)
_cell_measurement_reflns_used    4925
_cell_measurement_temperature    175(70)
_cell_measurement_theta_max      29.0020
_cell_measurement_theta_min      3.9700
_cell_volume                     2441.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      175(70)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -56.00   45.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -19.0000 -120.0000 101

  2 omega  -52.00   32.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -57.0000   30.0000 84

  3 omega   35.00   88.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -       15.7256  178.0000  150.0000 53

  4 omega  -29.00   49.00   1.0000    4.5600
omega____ theta____ kappa____ phi______ frames
    -      -16.8194   19.0000  120.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0152627000
_diffrn_orient_matrix_UB_12      -0.0225323000
_diffrn_orient_matrix_UB_13      -0.0380566000
_diffrn_orient_matrix_UB_21      -0.0459843000
_diffrn_orient_matrix_UB_22      -0.0322310000
_diffrn_orient_matrix_UB_23      -0.0025639000
_diffrn_orient_matrix_UB_31      -0.0383983000
_diffrn_orient_matrix_UB_32      0.0294949000
_diffrn_orient_matrix_UB_33      -0.0317634000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14787
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic greenish green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       plate
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.234
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0750P)^2^+2.0210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3886
_reflns_number_total             4979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qm00327k2.cif
_cod_data_source_block           lzy-tm-dpid
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '523-524' was changed to
'523.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2441.1(3)
_cod_original_formula_sum        'C30.50 H23 Cl N2 O4'
_cod_database_code               1554226
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 O(H) groups
2. Others
 Fixed Sof: C1(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00L(H00C,H00D)
3.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00I(H00I), C00K(H00K), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Z(H00Z), C010(H010), C011(H011)
3.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_shelx_res_checksum              5493
_shelx_hkl_checksum              37698
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-04-02
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method dichloromethane/hexane