#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:04:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178767 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/21/4102157.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_4102157
loop_
_publ_author_name
'Diego Bagnis'
'Luca Beverina'
'Hui Huang'
'Fabio Silvestri'
'Yan Yao'
'Henry Yan'
'Giorgio A. Pagani'
'Tobin J. Marks'
'Antonio Facchetti'
_publ_section_title
;
 Marked Alkyl- vs Alkenyl-Substitutent Effects on Squaraine Dye
 Solid-State Structure, Carrier Mobility, and Bulk-Heterojunction Solar
 Cell Efficiency
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4074
_journal_page_last               4075
_journal_paper_doi               10.1021/ja100520q
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C50 H48 N6 O2'
_chemical_formula_sum            'C50 H48 N6 O2'
_chemical_formula_weight         764.94
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.379(10)
_cell_angle_beta                 114.691(6)
_cell_angle_gamma                94.897(9)
_cell_formula_units_Z            1
_cell_length_a                   10.0064(9)
_cell_length_b                   10.014(2)
_cell_length_c                   11.6495(11)
_cell_measurement_reflns_used    507
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.68
_cell_measurement_theta_min      4.30
_cell_volume                     1026.3(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6003
_diffrn_reflns_theta_full        54.00
_diffrn_reflns_theta_max         61.27
_diffrn_reflns_theta_min         4.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.7880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1660
_reflns_number_total             2823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja100520q_si_002.cif
_cod_data_source_block           n0165
_cod_original_cell_volume        1026.3(2)
_cod_database_code               4102157
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.5404(3) 1.2331(3) 0.0319(2) 0.0345(6) Uani 1 1 d .
N1 N 0.2170(3) 0.9337(3) 0.0926(3) 0.0298(7) Uani 1 1 d .
N2 N -0.0385(3) 0.9910(3) 0.2335(3) 0.0321(7) Uani 1 1 d .
N3 N -0.1263(3) 0.9172(3) 0.2715(3) 0.0321(7) Uani 1 1 d .
C1 C 0.5194(4) 1.1070(4) 0.0140(3) 0.0299(9) Uani 1 1 d .
C2 C 0.4163(4) 1.0069(4) 0.0297(3) 0.0292(8) Uani 1 1 d .
C3 C 0.3096(4) 1.0317(3) 0.0754(3) 0.0280(9) Uani 1 1 d .
C4 C 0.2798(4) 1.1616(4) 0.1179(3) 0.0326(9) Uani 1 1 d .
H4 H 0.3252 1.2482 0.1165 0.039 Uiso 1 1 calc R
C5 C 0.1735(4) 1.1415(4) 0.1619(3) 0.0320(9) Uani 1 1 d .
H5 H 0.1329 1.2114 0.1966 0.038 Uiso 1 1 calc R
C6 C 0.1355(4) 0.9983(4) 0.1462(4) 0.0314(9) Uani 1 1 d .
C7 C 0.0360(4) 0.9239(4) 0.1813(3) 0.0319(9) Uani 1 1 d .
H7 H 0.0243 0.8263 0.1667 0.038 Uiso 1 1 calc R
C8 C 0.2113(4) 0.7846(3) 0.0656(4) 0.0334(9) Uani 1 1 d .
H8A H 0.2525 0.7585 0.0026 0.040 Uiso 1 1 calc R
H8B H 0.1057 0.7375 0.0251 0.040 Uiso 1 1 calc R
C9 C 0.2981(4) 0.7357(4) 0.1869(4) 0.0353(9) Uani 1 1 d .
H9A H 0.2826 0.7877 0.2597 0.042 Uiso 1 1 calc R
H9B H 0.4061 0.7557 0.2101 0.042 Uiso 1 1 calc R
C10 C 0.2511(4) 0.5815(4) 0.1695(4) 0.0401(10) Uani 1 1 d .
H10A H 0.2643 0.5298 0.0952 0.048 Uiso 1 1 calc R
H10B H 0.1436 0.5620 0.1481 0.048 Uiso 1 1 calc R
C11 C 0.3410(4) 0.5299(4) 0.2910(4) 0.0393(10) Uani 1 1 d .
H11A H 0.3368 0.5880 0.3674 0.047 Uiso 1 1 calc R
H11B H 0.2946 0.4341 0.2795 0.047 Uiso 1 1 calc R
C12 C 0.5011(5) 0.5335(4) 0.3167(4) 0.0423(10) Uani 1 1 d .
H12 H 0.5204 0.4885 0.2475 0.051 Uiso 1 1 calc R
C13 C 0.6182(5) 0.5948(5) 0.4286(5) 0.0490(11) Uani 1 1 d .
C14 C -0.1237(4) 0.7745(4) 0.2725(4) 0.0303(9) Uani 1 1 d .
C15 C -0.2412(4) 0.6737(4) 0.1765(4) 0.0342(9) Uani 1 1 d .
H15 H -0.3239 0.6992 0.1118 0.041 Uiso 1 1 calc R
C16 C -0.2358(4) 0.5359(4) 0.1765(4) 0.0393(10) Uani 1 1 d .
H16 H -0.3153 0.4664 0.1116 0.047 Uiso 1 1 calc R
C17 C -0.1150(5) 0.4993(4) 0.2709(4) 0.0420(10) Uani 1 1 d .
H17 H -0.1116 0.4048 0.2708 0.050 Uiso 1 1 calc R
C18 C 0.0010(4) 0.6006(4) 0.3652(4) 0.0403(10) Uani 1 1 d .
H18 H 0.0841 0.5752 0.4297 0.048 Uiso 1 1 calc R
C19 C -0.0033(4) 0.7374(4) 0.3662(4) 0.0334(9) Uani 1 1 d .
H19 H 0.0765 0.8065 0.4313 0.040 Uiso 1 1 calc R
C20 C -0.2111(4) 0.9918(4) 0.3221(3) 0.0306(9) Uani 1 1 d .
C21 C -0.2396(4) 1.1196(4) 0.2968(3) 0.0316(9) Uani 1 1 d .
H21 H -0.1992 1.1592 0.2473 0.038 Uiso 1 1 calc R
C22 C -0.3275(4) 1.1896(4) 0.3442(4) 0.0352(9) Uani 1 1 d .
H22 H -0.3488 1.2760 0.3255 0.042 Uiso 1 1 calc R
C23 C -0.3834(4) 1.1337(4) 0.4179(4) 0.0374(10) Uani 1 1 d .
H23 H -0.4429 1.1817 0.4506 0.045 Uiso 1 1 calc R
C24 C -0.3532(4) 1.0081(4) 0.4444(4) 0.0424(10) Uani 1 1 d .
H24 H -0.3917 0.9703 0.4960 0.051 Uiso 1 1 calc R
C25 C -0.2679(4) 0.9363(4) 0.3971(4) 0.0347(9) Uani 1 1 d .
H25 H -0.2482 0.8495 0.4157 0.042 Uiso 1 1 calc R
H2 H 0.727(5) 0.595(5) 0.443(4) 0.075(15) Uiso 1 1 d .
H1 H 0.607(5) 0.637(5) 0.519(5) 0.084(16) Uiso 1 1 d .
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'
N N 0.0311 0.0180 '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
C6 N1 C3 109.4(3) .
C6 N1 C8 123.8(3) .
C3 N1 C8 126.7(3) .
C7 N2 N3 117.6(3) .
N2 N3 C20 116.2(3) .
N2 N3 C14 122.6(3) .
C20 N3 C14 121.0(3) .
O1 C1 C2 133.7(3) .
O1 C1 C2 136.7(3) 2_675
C2 C1 C2 89.5(3) 2_675
C3 C2 C1 128.6(3) .
C3 C2 C1 140.9(3) 2_675
C1 C2 C1 90.5(3) 2_675
N1 C3 C2 126.7(3) .
N1 C3 C4 106.8(3) .
C2 C3 C4 126.5(3) .
C5 C4 C3 108.2(3) .
C5 C4 H4 125.9 .
C3 C4 H4 125.9 .
C4 C5 C6 107.7(3) .
C4 C5 H5 126.2 .
C6 C5 H5 126.2 .
N1 C6 C5 108.0(3) .
N1 C6 C7 121.9(3) .
C5 C6 C7 130.1(3) .
N2 C7 C6 119.4(3) .
N2 C7 H7 120.3 .
C6 C7 H7 120.3 .
N1 C8 C9 112.5(3) .
N1 C8 H8A 109.1 .
C9 C8 H8A 109.1 .
N1 C8 H8B 109.1 .
C9 C8 H8B 109.1 .
H8A C8 H8B 107.8 .
C8 C9 C10 112.5(3) .
C8 C9 H9A 109.1 .
C10 C9 H9A 109.1 .
C8 C9 H9B 109.1 .
C10 C9 H9B 109.1 .
H9A C9 H9B 107.8 .
C9 C10 C11 113.0(3) .
C9 C10 H10A 109.0 .
C11 C10 H10A 109.0 .
C9 C10 H10B 109.0 .
C11 C10 H10B 109.0 .
H10A C10 H10B 107.8 .
C12 C11 C10 112.2(3) .
C12 C11 H11A 109.2 .
C10 C11 H11A 109.2 .
C12 C11 H11B 109.2 .
C10 C11 H11B 109.2 .
H11A C11 H11B 107.9 .
C13 C12 C11 125.0(4) .
C13 C12 H12 117.5 .
C11 C12 H12 117.5 .
C12 C13 H2 123(3) .
C12 C13 H1 123(3) .
H2 C13 H1 114(4) .
C19 C14 C15 120.4(3) .
C19 C14 N3 119.9(3) .
C15 C14 N3 119.7(3) .
C16 C15 C14 119.2(4) .
C16 C15 H15 120.4 .
C14 C15 H15 120.4 .
C17 C16 C15 120.2(4) .
C17 C16 H16 119.9 .
C15 C16 H16 119.9 .
C16 C17 C18 119.9(4) .
C16 C17 H17 120.0 .
C18 C17 H17 120.0 .
C19 C18 C17 120.4(4) .
C19 C18 H18 119.8 .
C17 C18 H18 119.8 .
C18 C19 C14 119.9(4) .
C18 C19 H19 120.0 .
C14 C19 H19 120.0 .
C21 C20 C25 119.6(3) .
C21 C20 N3 120.8(3) .
C25 C20 N3 119.6(3) .
C20 C21 C22 119.9(3) .
C20 C21 H21 120.0 .
C22 C21 H21 120.0 .
C23 C22 C21 120.0(4) .
C23 C22 H22 120.0 .
C21 C22 H22 120.0 .
C22 C23 C24 120.0(3) .
C22 C23 H23 120.0 .
C24 C23 H23 120.0 .
C23 C24 C25 120.9(4) .
C23 C24 H24 119.5 .
C25 C24 H24 119.5 .
C24 C25 C20 119.6(4) .
C24 C25 H25 120.2 .
C20 C25 H25 120.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.227(4) .
N1 C6 1.359(4) .
N1 C3 1.391(4) .
N1 C8 1.460(4) .
N2 C7 1.302(4) .
N2 N3 1.359(4) .
N3 C20 1.411(4) .
N3 C14 1.433(4) .
C1 C2 1.466(5) .
C1 C2 1.471(5) 2_675
C2 C3 1.398(5) .
C2 C1 1.471(5) 2_675
C3 C4 1.409(5) .
C4 C5 1.375(5) .
C4 H4 0.9500 .
C5 C6 1.410(5) .
C5 H5 0.9500 .
C6 C7 1.426(5) .
C7 H7 0.9500 .
C8 C9 1.512(5) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.526(5) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.537(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.498(5) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.327(6) .
C12 H12 0.9500 .
C13 H2 1.03(5) .
C13 H1 1.12(5) .
C14 C19 1.380(5) .
C14 C15 1.394(5) .
C15 C16 1.385(5) .
C15 H15 0.9500 .
C16 C17 1.384(6) .
C16 H16 0.9500 .
C17 C18 1.384(6) .
C17 H17 0.9500 .
C18 C19 1.372(5) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.391(5) .
C20 C25 1.391(5) .
C21 C22 1.393(5) .
C21 H21 0.9500 .
C22 C23 1.373(5) .
C22 H22 0.9500 .
C23 C24 1.377(5) .
C23 H23 0.9500 .
C24 C25 1.380(5) .
C24 H24 0.9500 .
C25 H25 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 N2 N3 C20 -177.1(3) . .
C7 N2 N3 C14 8.7(5) . .
O1 C1 C2 C3 -1.7(6) . .
C2 C1 C2 C3 177.9(4) 2_675 .
O1 C1 C2 C1 -179.6(5) . 2_675
C2 C1 C2 C1 0.0 2_675 2_675
C6 N1 C3 C2 176.2(3) . .
C8 N1 C3 C2 -0.5(6) . .
C6 N1 C3 C4 -1.4(4) . .
C8 N1 C3 C4 -178.1(3) . .
C1 C2 C3 N1 -177.8(3) . .
C1 C2 C3 N1 -1.2(7) 2_675 .
C1 C2 C3 C4 -0.7(6) . .
C1 C2 C3 C4 175.9(4) 2_675 .
N1 C3 C4 C5 1.1(4) . .
C2 C3 C4 C5 -176.5(3) . .
C3 C4 C5 C6 -0.4(4) . .
C3 N1 C6 C5 1.2(4) . .
C8 N1 C6 C5 178.0(3) . .
C3 N1 C6 C7 -176.7(3) . .
C8 N1 C6 C7 0.1(5) . .
C4 C5 C6 N1 -0.5(4) . .
C4 C5 C6 C7 177.1(4) . .
N3 N2 C7 C6 -176.8(3) . .
N1 C6 C7 N2 179.3(3) . .
C5 C6 C7 N2 2.0(6) . .
C6 N1 C8 C9 -76.9(4) . .
C3 N1 C8 C9 99.4(4) . .
N1 C8 C9 C10 160.5(3) . .
C8 C9 C10 C11 178.7(3) . .
C9 C10 C11 C12 -68.4(4) . .
C10 C11 C12 C13 126.8(4) . .
N2 N3 C14 C19 72.9(4) . .
C20 N3 C14 C19 -101.1(4) . .
N2 N3 C14 C15 -105.4(4) . .
C20 N3 C14 C15 80.7(4) . .
C19 C14 C15 C16 0.2(5) . .
N3 C14 C15 C16 178.4(3) . .
C14 C15 C16 C17 -0.1(5) . .
C15 C16 C17 C18 -0.2(6) . .
C16 C17 C18 C19 0.3(6) . .
C17 C18 C19 C14 -0.1(5) . .
C15 C14 C19 C18 -0.1(5) . .
N3 C14 C19 C18 -178.3(3) . .
N2 N3 C20 C21 19.5(5) . .
C14 N3 C20 C21 -166.2(3) . .
N2 N3 C20 C25 -161.1(3) . .
C14 N3 C20 C25 13.2(5) . .
C25 C20 C21 C22 -1.4(5) . .
N3 C20 C21 C22 177.9(3) . .
C20 C21 C22 C23 1.3(5) . .
C21 C22 C23 C24 -0.4(6) . .
C22 C23 C24 C25 -0.4(6) . .
C23 C24 C25 C20 0.3(6) . .
C21 C20 C25 C24 0.7(5) . .
N3 C20 C25 C24 -178.7(3) . .
