Marked effects of indolyl vs. indolinyl substituent on solid-state structure, carrier mobility and photovoltaic efficiency of asymmetrical squaraine dyes
Yang, Lin; Yang, Qianqian; Yang, Daobin; Luo, Qian; Zhu, Youqin; Huang, Yan; Zhao, Suling; Lu, Zhiyun; J. Mater. Chem. A 2 (2014) 18313–; doi:10.1039/C4TA03859B

data_7235784
_publ_section_title
;
 Marked effects of indolyl vs. indolinyl substituent on solid-state
 structure, carrier mobility and photovoltaic efficiency of asymmetrical
 squaraine dyes
;
_journal_issue                   43
_journal_name_full               'J. Mater. Chem. A'
_journal_page_first              18313
_journal_paper_doi               10.1039/C4TA03859B
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C40 H36 N2 O4'
_chemical_formula_sum            'C40 H36 N2 O4'
_chemical_formula_weight         608.71
_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     iterative
_audit_creation_date             2013-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4709)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.732(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.41851(17)
_cell_length_b                   40.3306(11)
_cell_length_c                   11.5514(3)
_cell_measurement_reflns_used    8073
_cell_measurement_temperature    143.05(10)
_cell_measurement_theta_max      28.7560
_cell_measurement_theta_min      3.2020
_cell_volume                     3406.36(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      143.05(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    9.00   49.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143 -144.0000  -56.0000 400

  2 omega   57.00   89.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143 -144.0000  -56.0000 320

  3 omega   36.00   77.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143 -126.0000  111.0000 410

  4 omega  -25.00    0.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000   30.0000 250

  5 omega  -23.00   17.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  -99.0000 -150.0000 400

  6 omega  -48.00  -10.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174  144.0000   -3.0000 380

  7 omega   35.00   74.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143 -178.0000  -90.0000 390

  8 omega   35.00   94.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143  178.0000 -150.0000 590

  9 omega   -6.00   92.00   0.1000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       19.3143   38.0000  -30.0000 980
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0194281000
_diffrn_orient_matrix_UB_12      -0.0151997000
_diffrn_orient_matrix_UB_13      -0.0304796000
_diffrn_orient_matrix_UB_21      -0.0219184000
_diffrn_orient_matrix_UB_22      0.0087895000
_diffrn_orient_matrix_UB_23      -0.0537061000
_diffrn_orient_matrix_UB_31      0.0924647000
_diffrn_orient_matrix_UB_32      -0.0011104000
_diffrn_orient_matrix_UB_33      -0.0081218000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26126
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.963
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0727P)^2^+1.3228P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5792
_reflns_number_total             6964
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ta03859b2.cif
_cod_data_source_block           131118_s2_yl
_cod_database_code               7235784
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.80
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
3. Others
 Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17C)=
 Sof(H17D)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=
 Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15(H15C,H15D), C16A(H16A,H16B), C16B(H16C,H16D), C17A(H17A,
 H17B), C17B(H17C,H17D), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4A), C5(H5), C7(H7), C8(H8), C19(H19), C26(H26),
 C28(H28), C31(H31), C32(H32), C33(H33), C34(H34)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C18A(H18A,H18B,H18C), C18B(H18D,
 H18E,H18F)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              13406
_shelx_hkl_checksum              6068