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_7235785
_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 H38 N2 O4'
_chemical_formula_sum            'C40 H38 N2 O4'
_chemical_formula_weight         610.72
_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   mixed
_audit_creation_date             2013-07-05
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.803(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6013(7)
_cell_length_b                   15.3860(6)
_cell_length_c                   15.6472(9)
_cell_measurement_reflns_used    1499
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      59.18
_cell_measurement_theta_min      4.16
_cell_volume                     3080.8(3)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL-2012, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      140.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_av_unetI/netI     0.1352
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19712
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.557
_diffrn_reflns_theta_min         3.731
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1327 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.6475.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         5575
_refine_ls_number_restraints     340
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0777
_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^)+(0.0882P)^2^+1.1039P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2034
_refine_ls_wR_factor_ref         0.2364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3653
_reflns_number_total             5575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ta03859b2.cif
_cod_data_source_block           cu_dm13386_0m
_cod_database_code               7235785
_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
 N1-C21 \\sim N1-C21'
 with sigma of 0.01
 C17-C18 \\sim C18-C19 \\sim C20-C21 \\sim C17'-C18' \\sim C18'-C19' \\sim C20'-C21'
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C11' \\sim C12' \\sim C13' \\sim C14' \\sim C15' \\sim C16' \\sim C17' \\sim C18' \\sim C19' \\sim C20' \\sim C21': within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C11(0.7) C12(0.7) H12(0.7) C13(0.7) H13(0.7) C14(0.7) H14(0.7)
 C15(0.7) H15(0.7) C16(0.7) C17(0.7) H17(0.7) C18(0.7) H18A(0.7) H18B(0.7)
 C19(0.7) H19A(0.7) H19B(0.7) C20(0.7) H20A(0.7) H20B(0.7) C21(0.7) H21(0.7)
 C11'(0.3) C12'(0.3) H12'(0.3) C13'(0.3) H13'(0.3) C14'(0.3) H14'(0.3)
 C15'(0.3) H15'(0.3) C16'(0.3) C17'(0.3) H17'(0.3) C18'(0.3) H18C(0.3)
 H18D(0.3) C19'(0.3) H19C(0.3) H19D(0.3) C20'(0.3) H20C(0.3) H20D(0.3)
 C21'(0.3) H21'(0.3)
5.a Ternary CH refined with riding coordinates:
 C17(H17), C21(H21), C17'(H17'), C21'(H21')
5.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C18'(H18C,H18D), C19'(H19C,
 H19D), C20'(H20C,H20D), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
5.c Me refined with riding coordinates:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C12'(H12'),
 C13'(H13'), C14'(H14'), C15'(H15'), C22(H22), C27(H27), C28(H28), C29(H29),
 C30(H30), C32(H32), C33(H33)
5.e Fitted hexagon refined as free rotating group:
 C11(C12,C13,C14,C15,C16), C11'(C12',C13',C14',C15',C16')
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.948
_shelx_hkl_checksum              79418
_shelx_res_checksum              86178
_shelxl_version_number           2013-2