#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:17:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180472 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/41/7214131.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_7214131
loop_
_publ_author_name
'Brück, S'
'Krause, C.'
'Turrisi, R.'
'Beverina, L.'
'Wilken, S.'
'Saak, W.'
'Lützen, A'
'Borchert, H.'
'Schiek, M.'
'Parisi, J.'
_publ_section_title
;
 Structure-property relationship of anilino-squaraines in organic solar
 cells.
;
_journal_issue                   3
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              1067
_journal_page_last               1077
_journal_paper_doi               10.1039/c3cp54163k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C40 H60 N2 O6'
_chemical_formula_weight         664.90
_chemical_name_systematic
; 
1,3-bis[4-(N,N-di-n-hexylamino)-2,6-dihydroxyphenyl]-squaraine  
;
_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                96.374(10)
_cell_angle_beta                 94.825(11)
_cell_angle_gamma                97.872(11)
_cell_formula_units_Z            1
_cell_length_a                   5.097(2)
_cell_length_b                   10.746(5)
_cell_length_c                   16.604(7)
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.98
_cell_measurement_theta_min      2.48
_cell_volume                     890.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond Crystal Impact, 2010)'
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24735
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SAINT'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.2295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1387
_reflns_number_gt                2327
_reflns_number_total             3942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cp54163k_2.txt
_cod_data_source_block           sq2xy_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        890.6(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7214131
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 1.1280(3) 0.85108(14) 1.07444(9) 0.0226(4) Uani 1 1 d .
O2 O 0.4457(3) 0.99800(15) 0.85120(10) 0.0249(4) Uani 1 1 d .
H2 H 0.584(6) 1.055(2) 0.8753(15) 0.036(8) Uiso 1 1 d .
O3 O 0.7115(3) 0.68017(15) 1.01645(10) 0.0244(4) Uani 1 1 d .
H3 H 0.860(7) 0.740(3) 1.0377(18) 0.058(10) Uiso 1 1 d .
N1 N -0.0644(4) 0.59350(16) 0.83033(11) 0.0191(4) Uani 1 1 d .
C1 C 1.0568(5) 0.9340(2) 1.03316(13) 0.0189(5) Uani 1 1 d .
C2 C 0.8322(4) 0.93613(19) 0.97365(13) 0.0171(5) Uani 1 1 d .
C3 C 0.6079(4) 0.85032(19) 0.93858(13) 0.0170(5) Uani 1 1 d .
C4 C 0.4201(5) 0.88236(19) 0.87768(13) 0.0182(5) Uani 1 1 d .
C5 C 0.2053(5) 0.7984(2) 0.84271(13) 0.0189(5) Uani 1 1 d .
H5 H 0.0885 0.8232 0.8018 0.023 Uiso 1 1 calc R
C6 C 0.1511(4) 0.6747(2) 0.86584(13) 0.0180(5) Uani 1 1 d .
C7 C 0.3324(5) 0.6410(2) 0.92632(13) 0.0191(5) Uani 1 1 d .
H7 H 0.3017 0.5592 0.9434 0.023 Uiso 1 1 calc R
C8 C 0.5501(5) 0.7241(2) 0.96045(13) 0.0182(5) Uani 1 1 d .
C9 C -0.2489(5) 0.6305(2) 0.76749(13) 0.0208(5) Uani 1 1 d .
H9A H -0.2781 0.7185 0.7843 0.025 Uiso 1 1 calc R
H9B H -0.4224 0.5754 0.7651 0.025 Uiso 1 1 calc R
C10 C -0.1578(5) 0.6233(2) 0.68229(14) 0.0227(5) Uani 1 1 d .
H10A H 0.0075 0.6837 0.6826 0.027 Uiso 1 1 calc R
H10B H -0.1181 0.5370 0.6657 0.027 Uiso 1 1 calc R
C11 C -0.3717(5) 0.6545(2) 0.62132(14) 0.0246(6) Uani 1 1 d .
H11A H -0.5319 0.5901 0.6189 0.030 Uiso 1 1 calc R
H11B H -0.4215 0.7375 0.6412 0.030 Uiso 1 1 calc R
C12 C -0.2894(5) 0.6593(2) 0.53564(14) 0.0278(6) Uani 1 1 d .
H12A H -0.2442 0.5757 0.5151 0.033 Uiso 1 1 calc R
H12B H -0.1269 0.7223 0.5381 0.033 Uiso 1 1 calc R
C13 C -0.5032(6) 0.6939(2) 0.47534(15) 0.0321(6) Uani 1 1 d .
H13A H -0.4578 0.6719 0.4192 0.039 Uiso 1 1 calc R
H13B H -0.6760 0.6427 0.4811 0.039 Uiso 1 1 calc R
C14 C -0.5327(6) 0.8333(2) 0.48782(17) 0.0403(7) Uani 1 1 d .
H14A H -0.5853 0.8549 0.5425 0.060 Uiso 1 1 calc R
H14B H -0.6692 0.8503 0.4470 0.060 Uiso 1 1 calc R
H14C H -0.3624 0.8846 0.4821 0.060 Uiso 1 1 calc R
C15 C -0.1545(5) 0.4698(2) 0.85739(14) 0.0214(5) Uani 1 1 d .
H15A H -0.3357 0.4699 0.8747 0.026 Uiso 1 1 calc R
H15B H -0.0350 0.4586 0.9054 0.026 Uiso 1 1 calc R
C16 C -0.1593(5) 0.3580(2) 0.79190(14) 0.0217(5) Uani 1 1 d .
H16A H -0.2650 0.3731 0.7421 0.026 Uiso 1 1 calc R
H16B H -0.2496 0.2807 0.8109 0.026 Uiso 1 1 calc R
C17 C 0.1174(5) 0.3356(2) 0.77061(14) 0.0237(5) Uani 1 1 d .
H17A H 0.2103 0.4144 0.7541 0.028 Uiso 1 1 calc R
H17B H 0.2202 0.3171 0.8201 0.028 Uiso 1 1 calc R
C18 C 0.1169(5) 0.2276(2) 0.70266(15) 0.0262(6) Uani 1 1 d .
H18A H 0.0304 0.2501 0.6517 0.031 Uiso 1 1 calc R
H18B H 0.3035 0.2189 0.6937 0.031 Uiso 1 1 calc R
C19 C -0.0249(5) 0.1000(2) 0.71927(15) 0.0275(6) Uani 1 1 d .
H19A H -0.2195 0.1012 0.7144 0.033 Uiso 1 1 calc R
H19B H 0.0305 0.0860 0.7757 0.033 Uiso 1 1 calc R
C20 C 0.0373(6) -0.0089(2) 0.66018(16) 0.0373(7) Uani 1 1 d .
H20A H -0.0113 0.0063 0.6041 0.056 Uiso 1 1 calc R
H20B H -0.0649 -0.0885 0.6708 0.056 Uiso 1 1 calc R
H20C H 0.2280 -0.0143 0.6677 0.056 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_1
_geom_angle_site_symmetry_3
C4 O2 H2 116.0(17) . .
C8 O3 H3 112.7(19) . .
C6 N1 C9 121.21(18) . .
C6 N1 C15 124.11(18) . .
C9 N1 C15 114.22(18) . .
O1 C1 C2 133.6(2) . .
O1 C1 C2 133.8(2) . 2_777
C2 C1 C2 92.66(17) . 2_777
O1 C1 C1 179.8(2) . 2_777
C2 C1 C1 46.33(13) . 2_777
C2 C1 C1 46.33(12) 2_777 2_777
C3 C2 C1 136.1(2) . .
C3 C2 C1 136.6(2) . 2_777
C1 C2 C1 87.34(17) . 2_777
C2 C3 C4 122.11(19) . .
C2 C3 C8 122.77(19) . .
C4 C3 C8 115.12(19) . .
O2 C4 C5 115.76(19) . .
O2 C4 C3 122.15(19) . .
C5 C4 C3 122.10(19) . .
C4 C5 C6 121.7(2) . .
C4 C5 H5 119.1 . .
C6 C5 H5 119.1 . .
N1 C6 C7 122.25(19) . .
N1 C6 C5 120.48(19) . .
C7 C6 C5 117.3(2) . .
C8 C7 C6 121.1(2) . .
C8 C7 H7 119.4 . .
C6 C7 H7 119.4 . .
O3 C8 C7 115.69(19) . .
O3 C8 C3 121.68(19) . .
C7 C8 C3 122.6(2) . .
N1 C9 C10 115.3(2) . .
N1 C9 H9A 108.5 . .
C10 C9 H9A 108.5 . .
N1 C9 H9B 108.5 . .
C10 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C11 C10 C9 110.7(2) . .
C11 C10 H10A 109.5 . .
C9 C10 H10A 109.5 . .
C11 C10 H10B 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C12 C11 C10 114.3(2) . .
C12 C11 H11A 108.7 . .
C10 C11 H11A 108.7 . .
C12 C11 H11B 108.7 . .
C10 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C11 C12 C13 113.9(2) . .
C11 C12 H12A 108.8 . .
C13 C12 H12A 108.8 . .
C11 C12 H12B 108.8 . .
C13 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
C14 C13 C12 113.0(2) . .
C14 C13 H13A 109.0 . .
C12 C13 H13A 109.0 . .
C14 C13 H13B 109.0 . .
C12 C13 H13B 109.0 . .
H13A C13 H13B 107.8 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C15 C16 113.50(19) . .
N1 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
N1 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C15 C16 C17 113.38(19) . .
C15 C16 H16A 108.9 . .
C17 C16 H16A 108.9 . .
C15 C16 H16B 108.9 . .
C17 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
C18 C17 C16 114.27(19) . .
C18 C17 H17A 108.7 . .
C16 C17 H17A 108.7 . .
C18 C17 H17B 108.7 . .
C16 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C19 C18 C17 114.4(2) . .
C19 C18 H18A 108.7 . .
C17 C18 H18A 108.7 . .
C19 C18 H18B 108.7 . .
C17 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
C18 C19 C20 111.9(2) . .
C18 C19 H19A 109.2 . .
C20 C19 H19A 109.2 . .
C18 C19 H19B 109.2 . .
C20 C19 H19B 109.2 . .
H19A C19 H19B 107.9 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.256(3) .
O2 C4 1.357(3) .
O2 H2 0.90(3) .
O3 C8 1.356(3) .
O3 H3 0.94(3) .
N1 C6 1.353(3) .
N1 C9 1.470(3) .
N1 C15 1.476(3) .
C1 C2 1.452(3) .
C1 C2 1.452(3) 2_777
C1 C1 2.006(4) 2_777
C2 C3 1.406(3) .
C2 C1 1.452(3) 2_777
C3 C4 1.436(3) .
C3 C8 1.441(3) .
C4 C5 1.362(3) .
C5 C6 1.422(3) .
C5 H5 0.9500 .
C6 C7 1.417(3) .
C7 C8 1.363(3) .
C7 H7 0.9500 .
C9 C10 1.523(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.522(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.521(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.529(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.519(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.524(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.527(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.526(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.524(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.527(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
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
O1 C1 C2 C3 0.3(5) . .
C2 C1 C2 C3 -180.0(3) 2_777 .
C1 C1 C2 C3 -180.0(3) 2_777 .
O1 C1 C2 C1 -179.7(3) . 2_777
C2 C1 C2 C1 0.0 2_777 2_777
C1 C2 C3 C4 -178.4(2) . .
C1 C2 C3 C4 1.6(4) 2_777 .
C1 C2 C3 C8 1.2(4) . .
C1 C2 C3 C8 -178.8(2) 2_777 .
C2 C3 C4 O2 -1.0(3) . .
C8 C3 C4 O2 179.4(2) . .
C2 C3 C4 C5 178.9(2) . .
C8 C3 C4 C5 -0.8(3) . .
O2 C4 C5 C6 -178.7(2) . .
C3 C4 C5 C6 1.4(3) . .
C9 N1 C6 C7 -179.8(2) . .
C15 N1 C6 C7 8.5(3) . .
C9 N1 C6 C5 -0.3(3) . .
C15 N1 C6 C5 -172.1(2) . .
C4 C5 C6 N1 179.7(2) . .
C4 C5 C6 C7 -0.8(3) . .
N1 C6 C7 C8 179.1(2) . .
C5 C6 C7 C8 -0.3(3) . .
C6 C7 C8 O3 -178.8(2) . .
C6 C7 C8 C3 0.9(3) . .
C2 C3 C8 O3 -0.3(3) . .
C4 C3 C8 O3 179.3(2) . .
C2 C3 C8 C7 -180.0(2) . .
C4 C3 C8 C7 -0.4(3) . .
C6 N1 C9 C10 80.3(3) . .
C15 N1 C9 C10 -107.2(2) . .
N1 C9 C10 C11 175.97(18) . .
C9 C10 C11 C12 175.56(19) . .
C10 C11 C12 C13 -178.62(19) . .
C11 C12 C13 C14 74.5(3) . .
C6 N1 C15 C16 -120.1(2) . .
C9 N1 C15 C16 67.6(3) . .
N1 C15 C16 C17 68.1(2) . .
C15 C16 C17 C18 -177.57(19) . .
C16 C17 C18 C19 -57.4(3) . .
C17 C18 C19 C20 -166.3(2) . .
