#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/20/4002040.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_4002040
loop_
_publ_author_name
'Zitzler-Kunkel, André'
'Lenze, Martin R.'
'Kronenberg, Nils M.'
'Krause, Ana-Maria'
'Stolte, Matthias'
'Meerholz, Klaus'
'Würthner, Frank'
_publ_section_title
;
 NIR-Absorbing Merocyanine Dyes for BHJ Solar Cells
;
_journal_issue                   16
_journal_name_full               'Chemistry of Materials'
_journal_page_first              4856
_journal_paper_doi               10.1021/cm502302s
_journal_volume                  26
_journal_year                    2014
_chemical_formula_moiety         'C27 H27 N3 O S'
_chemical_formula_sum            'C27 H27 N3 O S'
_chemical_formula_weight         441.58
_chemical_name_systematic
;
2-{(Z)-2-[(E)-3-(5-Dibutylamino-thiophene-2-yl)-allylidene]-
3-oxo-indan-1-ylidene}-malononitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2013
_cell_angle_alpha                70.6420(10)
_cell_angle_beta                 69.2110(10)
_cell_angle_gamma                65.5950(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8153(3)
_cell_length_b                   10.5285(4)
_cell_length_c                   13.4153(5)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.61
_cell_volume                     1152.13(7)
_computing_cell_refinement       Bruker-SAINT-V8.30-C
_computing_data_collection       Bruker-APEX2-2013/4-1
_computing_data_reduction        Bruker-SAINT-V8.30-C
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_Photon100
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15684
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.610
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker, 2008)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²+0.4236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3867
_reflns_number_total             4166
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            CCDC_1007697(4).cif
_cod_data_source_block           032_AZ168_MG
_cod_depositor_comments
'Adding full bibliography for 4002040--4002042.cif.'
_cod_database_code               4002040
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.768
_shelx_estimated_absorpt_t_max   0.928
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.83154(14) 0.40146(13) 0.84638(10) 0.0195(3) Uani 1 1 d . .
C2 C 0.82792(15) 0.38774(13) 0.74591(10) 0.0218(3) Uani 1 1 d . .
H2 H 0.7880 0.3231 0.7400 0.026 Uiso 1 1 calc R U
C3 C 0.88850(15) 0.47822(14) 0.65833(10) 0.0229(3) Uani 1 1 d . .
H3 H 0.8927 0.4826 0.5855 0.028 Uiso 1 1 calc R U
C4 C 0.94423(14) 0.56440(13) 0.68343(10) 0.0216(3) Uani 1 1 d . .
C5 C 1.01122(14) 0.66395(14) 0.61097(10) 0.0223(3) Uani 1 1 d . .
H5 H 1.0222 0.6737 0.5358 0.027 Uiso 1 1 calc R U
C6 C 1.06442(14) 0.75137(13) 0.63478(10) 0.0215(3) Uani 1 1 d . .
H6 H 1.0515 0.7498 0.7087 0.026 Uiso 1 1 calc R U
C7 C 1.13609(14) 0.84071(13) 0.55153(10) 0.0209(3) Uani 1 1 d . .
H7 H 1.1481 0.8368 0.4790 0.025 Uiso 1 1 calc R U
C8 C 1.19282(14) 0.93621(13) 0.56253(10) 0.0196(3) Uani 1 1 d . .
C9 C 1.27336(14) 1.02530(13) 0.47729(10) 0.0189(3) Uani 1 1 d . .
C10 C 1.29396(14) 1.11945(13) 0.52902(10) 0.0201(3) Uani 1 1 d . .
C11 C 1.36240(15) 1.22511(14) 0.48602(11) 0.0245(3) Uani 1 1 d . .
H11 H 1.4077 1.2486 0.4099 0.029 Uiso 1 1 calc R U
C12 C 1.36293(16) 1.29564(14) 0.55733(11) 0.0271(3) Uani 1 1 d . .
H12 H 1.4088 1.3683 0.5289 0.032 Uiso 1 1 calc R U
C13 C 1.29783(16) 1.26224(15) 0.66908(11) 0.0275(3) Uani 1 1 d . .
H13 H 1.2990 1.3124 0.7158 0.033 Uiso 1 1 calc R U
C14 C 1.23089(15) 1.15537(14) 0.71263(11) 0.0248(3) Uani 1 1 d . .
H14 H 1.1869 1.1309 0.7889 0.030 Uiso 1 1 calc R U
C15 C 1.23051(14) 1.08614(13) 0.64165(10) 0.0206(3) Uani 1 1 d . .
C16 C 1.16766(14) 0.96907(13) 0.66751(10) 0.0202(3) Uani 1 1 d . .
C17 C 1.32655(14) 1.02692(13) 0.36663(10) 0.0207(3) Uani 1 1 d . .
C18 C 1.31692(15) 0.92881(14) 0.31894(10) 0.0240(3) Uani 1 1 d . .
C19 C 1.39762(15) 1.12669(14) 0.28774(10) 0.0238(3) Uani 1 1 d . .
C20 C 0.77929(15) 0.36592(13) 1.04401(10) 0.0214(3) Uani 1 1 d . .
H20A H 0.8754 0.3858 1.0300 0.026 Uiso 1 1 calc R U
H20B H 0.7784 0.2821 1.1057 0.026 Uiso 1 1 calc R U
C21 C 0.63937(14) 0.49514(13) 1.07494(10) 0.0210(3) Uani 1 1 d . .
H21A H 0.5436 0.4732 1.0922 0.025 Uiso 1 1 calc R U
H21B H 0.6375 0.5774 1.0117 0.025 Uiso 1 1 calc R U
C22 C 0.64242(15) 0.53626(14) 1.17358(10) 0.0226(3) Uani 1 1 d . .
H22A H 0.7492 0.5295 1.1658 0.027 Uiso 1 1 calc R U
H22B H 0.5753 0.6369 1.1738 0.027 Uiso 1 1 calc R U
C23 C 0.58848(16) 0.44222(15) 1.28223(11) 0.0263(3) Uani 1 1 d . .
H23A H 0.4794 0.4557 1.2940 0.039 Uiso 1 1 calc R U
H23B H 0.6005 0.4685 1.3414 0.039 Uiso 1 1 calc R U
H23C H 0.6508 0.3418 1.2812 0.039 Uiso 1 1 calc R U
C24 C 0.69535(14) 0.23488(13) 0.96360(10) 0.0203(3) Uani 1 1 d . .
H24A H 0.6456 0.2653 0.9031 0.024 Uiso 1 1 calc R U
H24B H 0.6125 0.2424 1.0323 0.024 Uiso 1 1 calc R U
C25 C 0.79944(14) 0.07958(13) 0.96993(11) 0.0214(3) Uani 1 1 d . .
H25A H 0.8533 0.0489 1.0282 0.026 Uiso 1 1 calc R U
H25B H 0.8786 0.0694 0.8998 0.026 Uiso 1 1 calc R U
C26 C 0.70245(15) -0.01455(14) 0.99430(11) 0.0238(3) Uani 1 1 d . .
H26A H 0.6329 -0.0133 1.0687 0.029 Uiso 1 1 calc R U
H26B H 0.6371 0.0258 0.9420 0.029 Uiso 1 1 calc R U
C27 C 0.80105(18) -0.16863(15) 0.98653(12) 0.0336(3) Uani 1 1 d . .
H27A H 0.8733 -0.1704 0.9141 0.050 Uiso 1 1 calc R U
H27B H 0.7340 -0.2227 0.9980 0.050 Uiso 1 1 calc R U
H27C H 0.8593 -0.2119 1.0425 0.050 Uiso 1 1 calc R U
N1 N 0.77799(12) 0.33287(11) 0.94614(8) 0.0200(2) Uani 1 1 d . .
N2 N 1.31359(15) 0.85017(14) 0.27800(10) 0.0339(3) Uani 1 1 d . .
N3 N 1.45335(15) 1.20544(13) 0.22134(9) 0.0336(3) Uani 1 1 d . .
O1 O 1.10650(11) 0.91422(10) 0.75949(7) 0.0257(2) Uani 1 1 d . .
S1 S 0.91659(3) 0.52764(3) 0.82541(2) 0.02062(10) Uani 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'
S S 0.3331 0.5567 '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
N1 C1 C2 127.54(11)
N1 C1 S1 121.40(10)
C2 C1 S1 111.06(9)
C3 C2 C1 112.33(11)
C3 C2 H2 123.8
C1 C2 H2 123.8
C2 C3 C4 115.49(12)
C2 C3 H3 122.3
C4 C3 H3 122.3
C5 C4 C3 127.35(12)
C5 C4 S1 123.27(10)
C3 C4 S1 109.38(9)
C4 C5 C6 127.93(12)
C4 C5 H5 116.0
C6 C5 H5 116.0
C7 C6 C5 120.54(12)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 127.12(12)
C6 C7 H7 116.4
C8 C7 H7 116.4
C7 C8 C9 127.91(11)
C7 C8 C16 123.77(11)
C9 C8 C16 108.19(11)
C17 C9 C8 128.39(12)
C17 C9 C10 123.97(11)
C8 C9 C10 107.64(10)
C11 C10 C15 119.27(12)
C11 C10 C9 132.24(12)
C15 C10 C9 108.48(11)
C10 C11 C12 118.42(12)
C10 C11 H11 120.8
C12 C11 H11 120.8
C13 C12 C11 121.59(12)
C13 C12 H12 119.2
C11 C12 H12 119.2
C12 C13 C14 120.17(12)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 117.96(12)
C15 C14 H14 121.0
C13 C14 H14 121.0
C14 C15 C10 122.58(12)
C14 C15 C16 128.28(12)
C10 C15 C16 109.14(11)
O1 C16 C8 128.44(12)
O1 C16 C15 125.06(11)
C8 C16 C15 106.50(10)
C9 C17 C18 123.57(11)
C9 C17 C19 123.60(12)
C18 C17 C19 112.84(11)
N2 C18 C17 177.74(14)
N3 C19 C17 177.27(14)
N1 C20 C21 111.18(10)
N1 C20 H20A 109.4
C21 C20 H20A 109.4
N1 C20 H20B 109.4
C21 C20 H20B 109.4
H20A C20 H20B 108.0
C20 C21 C22 112.13(10)
C20 C21 H21A 109.2
C22 C21 H21A 109.2
C20 C21 H21B 109.2
C22 C21 H21B 109.2
H21A C21 H21B 107.9
C23 C22 C21 113.17(11)
C23 C22 H22A 108.9
C21 C22 H22A 108.9
C23 C22 H22B 108.9
C21 C22 H22B 108.9
H22A C22 H22B 107.8
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
N1 C24 C25 113.53(10)
N1 C24 H24A 108.9
C25 C24 H24A 108.9
N1 C24 H24B 108.9
C25 C24 H24B 108.9
H24A C24 H24B 107.7
C24 C25 C26 109.73(10)
C24 C25 H25A 109.7
C26 C25 H25A 109.7
C24 C25 H25B 109.7
C26 C25 H25B 109.7
H25A C25 H25B 108.2
C27 C26 C25 112.72(11)
C27 C26 H26A 109.0
C25 C26 H26A 109.0
C27 C26 H26B 109.0
C25 C26 H26B 109.0
H26A C26 H26B 107.8
C26 C27 H27A 109.5
C26 C27 H27B 109.5
H27A C27 H27B 109.5
C26 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
C1 N1 C20 121.52(10)
C1 N1 C24 121.01(10)
C20 N1 C24 116.95(10)
C1 S1 C4 91.73(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3276(16)
C1 C2 1.4164(18)
C1 S1 1.7444(12)
C2 C3 1.3681(18)
C2 H2 0.9500
C3 C4 1.4068(18)
C3 H3 0.9500
C4 C5 1.3842(18)
C4 S1 1.7558(13)
C5 C6 1.3900(18)
C5 H5 0.9500
C6 C7 1.3855(18)
C6 H6 0.9500
C7 C8 1.4007(18)
C7 H7 0.9500
C8 C9 1.4396(17)
C8 C16 1.4730(17)
C9 C17 1.3846(18)
C9 C10 1.4922(17)
C10 C11 1.3923(18)
C10 C15 1.3982(18)
C11 C12 1.3943(19)
C11 H11 0.9500
C12 C13 1.391(2)
C12 H12 0.9500
C13 C14 1.3935(19)
C13 H13 0.9500
C14 C15 1.3794(18)
C14 H14 0.9500
C15 C16 1.4877(17)
C16 O1 1.2266(15)
C17 C18 1.4307(18)
C17 C19 1.4334(18)
C18 N2 1.1510(18)
C19 N3 1.1486(18)
C20 N1 1.4709(16)
C20 C21 1.5281(17)
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.5356(17)
C21 H21A 0.9900
C21 H21B 0.9900
C22 C23 1.5211(18)
C22 H22A 0.9900
C22 H22B 0.9900
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 N1 1.4743(15)
C24 C25 1.5209(17)
C24 H24A 0.9900
C24 H24B 0.9900
C25 C26 1.5294(17)
C25 H25A 0.9900
C25 H25B 0.9900
C26 C27 1.5239(18)
C26 H26A 0.9900
C26 H26B 0.9900
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 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
N1 C1 C2 C3 177.84(12)
S1 C1 C2 C3 -1.28(14)
C1 C2 C3 C4 0.99(17)
C2 C3 C4 C5 179.74(13)
C2 C3 C4 S1 -0.25(15)
C3 C4 C5 C6 178.85(13)
S1 C4 C5 C6 -1.2(2)
C4 C5 C6 C7 176.70(12)
C5 C6 C7 C8 178.72(12)
C6 C7 C8 C9 177.10(12)
C6 C7 C8 C16 -7.7(2)
C7 C8 C9 C17 -7.0(2)
C16 C8 C9 C17 177.13(12)
C7 C8 C9 C10 173.73(12)
C16 C8 C9 C10 -2.10(13)
C17 C9 C10 C11 1.0(2)
C8 C9 C10 C11 -179.74(13)
C17 C9 C10 C15 -178.22(12)
C8 C9 C10 C15 1.05(14)
C15 C10 C11 C12 -0.96(19)
C9 C10 C11 C12 179.90(13)
C10 C11 C12 C13 0.3(2)
C11 C12 C13 C14 0.5(2)
C12 C13 C14 C15 -0.6(2)
C13 C14 C15 C10 -0.12(19)
C13 C14 C15 C16 179.64(12)
C11 C10 C15 C14 0.90(19)
C9 C10 C15 C14 -179.77(12)
C11 C10 C15 C16 -178.91(11)
C9 C10 C15 C16 0.42(14)
C7 C8 C16 O1 5.7(2)
C9 C8 C16 O1 -178.21(12)
C7 C8 C16 C15 -173.71(11)
C9 C8 C16 C15 2.33(13)
C14 C15 C16 O1 -1.0(2)
C10 C15 C16 O1 178.82(12)
C14 C15 C16 C8 178.52(13)
C10 C15 C16 C8 -1.70(13)
C8 C9 C17 C18 -4.1(2)
C10 C9 C17 C18 174.98(12)
C8 C9 C17 C19 176.12(12)
C10 C9 C17 C19 -4.8(2)
N1 C20 C21 C22 -177.18(10)
C20 C21 C22 C23 -79.44(14)
N1 C24 C25 C26 176.92(10)
C24 C25 C26 C27 172.17(11)
C2 C1 N1 C20 -175.35(12)
S1 C1 N1 C20 3.68(16)
C2 C1 N1 C24 -3.90(19)
S1 C1 N1 C24 175.14(9)
C21 C20 N1 C1 82.88(14)
C21 C20 N1 C24 -88.90(13)
C25 C24 N1 C1 94.20(14)
C25 C24 N1 C20 -93.97(13)
N1 C1 S1 C4 -178.22(11)
C2 C1 S1 C4 0.97(10)
C5 C4 S1 C1 179.59(11)
C3 C4 S1 C1 -0.42(10)
