#------------------------------------------------------------------------------
#$Date: 2015-12-09 14:57:02 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171067 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/17/7221739.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_7221739
loop_
_publ_author_name
'Jindo, Takumi'
'Kim, Byung-Soon'
'Sasaki, Naho'
'Shinohara, Yohei'
'Son, Young-A'
'Kim, Sung-Hoon'
'Matsumoto, Shinya'
_publ_section_title
;
 The effect of terminal dimethyl and diethyl substituents on the
 J-aggregate-like molecular arrangement of bisazomethine dye molecules
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7213
_journal_paper_doi               10.1039/C5CE00845J
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C42 H62 N6 O2'
_chemical_formula_sum            'C42 H62 N6 O2'
_chemical_formula_weight         682.99
_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_update_record
;
2015-07-13 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                94.067(4)
_cell_angle_beta                 93.088(4)
_cell_angle_gamma                112.605(4)
_cell_formula_units_Z            1
_cell_length_a                   8.6252(3)
_cell_length_b                   10.9509(5)
_cell_length_c                   11.5620(7)
_cell_measurement_reflns_used    706
_cell_measurement_temperature    93
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      22.10
_cell_volume                     1001.73(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.32a (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.32a (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_laue_measured_fraction_full 0.989
_diffrn_reflns_laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14895
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         75.452
_diffrn_reflns_theta_min         3.848
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.32a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            reddishpurple
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             372.00
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0974P)²+0.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3199
_reflns_number_total             4000
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c5ce00845j2.cif
_cod_data_source_block           SX333_18
_cod_depositor_comments
'Adding full bibliography for 7221734--7221739.cif.'
_cod_original_cell_volume        1001.74(9)
_cod_database_code               7221739
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
O1 O 0.55772(12) 0.93250(10) 0.19661(10) 0.0264(3) Uani 1 1 d . .
N1 N -0.04026(17) 0.73483(14) 0.07548(13) 0.0332(3) Uani 1 1 d . .
N2 N 0.22449(15) 1.06506(12) 0.04909(11) 0.0243(3) Uani 1 1 d . .
N3 N 1.01550(15) 1.36168(12) 0.20846(12) 0.0275(3) Uani 1 1 d . .
C1 C -0.00058(18) 0.84185(15) 0.05127(13) 0.0251(3) Uani 1 1 d . .
C2 C 0.05827(18) 0.97873(14) 0.02434(13) 0.0235(3) Uani 1 1 d . .
C3 C 0.33347(18) 1.02241(15) 0.09291(13) 0.0243(3) Uani 1 1 d . .
H3 H 0.2974 0.9317 0.1072 0.029 Uiso 1 1 calc R U
C4 C 0.50761(18) 1.10894(15) 0.12041(13) 0.0231(3) Uani 1 1 d . .
C5 C 0.57115(19) 1.24202(15) 0.09488(13) 0.0250(3) Uani 1 1 d . .
H5 H 0.4963 1.2753 0.0582 0.030 Uiso 1 1 calc R U
C6 C 0.73708(19) 1.32574(15) 0.12079(13) 0.0255(3) Uani 1 1 d . .
H6 H 0.7754 1.4146 0.1009 0.031 Uiso 1 1 calc R U
C7 C 0.85145(18) 1.27962(15) 0.17733(13) 0.0243(3) Uani 1 1 d . .
C8 C 0.79036(18) 1.14566(15) 0.20216(13) 0.0238(3) Uani 1 1 d . .
H8 H 0.8652 1.1122 0.2386 0.029 Uiso 1 1 calc R U
C9 C 0.62286(18) 1.06244(14) 0.17416(13) 0.0230(3) Uani 1 1 d . .
C10 C 0.67199(18) 0.87843(15) 0.24409(14) 0.0263(3) Uani 1 1 d . .
H10A H 0.7246 0.9264 0.3210 0.032 Uiso 1 1 calc R U
H10B H 0.7625 0.8888 0.1918 0.032 Uiso 1 1 calc R U
C11 C 0.57498(19) 0.73299(15) 0.25659(14) 0.0268(3) Uani 1 1 d . .
H11A H 0.5323 0.6838 0.1787 0.032 Uiso 1 1 calc R U
H11B H 0.4770 0.7223 0.3017 0.032 Uiso 1 1 calc R U
C12 C 0.68928(19) 0.67620(15) 0.31878(15) 0.0275(4) Uani 1 1 d . .
H12A H 0.7856 0.6866 0.2720 0.033 Uiso 1 1 calc R U
H12B H 0.7352 0.7294 0.3947 0.033 Uiso 1 1 calc R U
C13 C 0.60399(19) 0.53051(15) 0.33991(14) 0.0263(3) Uani 1 1 d . .
H13A H 0.5626 0.4758 0.2642 0.032 Uiso 1 1 calc R U
H13B H 0.5055 0.5184 0.3849 0.032 Uiso 1 1 calc R U
C14 C 0.72443(19) 0.48312(15) 0.40626(14) 0.0275(4) Uani 1 1 d . .
H14A H 0.8228 0.4965 0.3608 0.033 Uiso 1 1 calc R U
H14B H 0.7663 0.5395 0.4812 0.033 Uiso 1 1 calc R U
C15 C 0.64872(19) 0.33820(15) 0.43138(14) 0.0264(3) Uani 1 1 d . .
H15A H 0.6078 0.2807 0.3570 0.032 Uiso 1 1 calc R U
H15B H 0.5508 0.3238 0.4775 0.032 Uiso 1 1 calc R U
C16 C 0.77685(19) 0.29882(15) 0.49804(14) 0.0290(4) Uani 1 1 d . .
H16A H 0.8757 0.3165 0.4523 0.035 Uiso 1 1 calc R U
H16B H 0.8159 0.3563 0.5725 0.035 Uiso 1 1 calc R U
C17 C 0.7117(2) 0.15421(15) 0.52435(14) 0.0286(4) Uani 1 1 d . .
H17A H 0.6147 0.1363 0.5719 0.034 Uiso 1 1 calc R U
H17B H 0.6712 0.0960 0.4503 0.034 Uiso 1 1 calc R U
C18 C 0.8454(2) 0.12008(18) 0.58879(18) 0.0398(4) Uani 1 1 d . .
H18A H 0.8851 0.1782 0.6629 0.048 Uiso 1 1 calc R U
H18B H 0.9428 0.1394 0.5414 0.048 Uiso 1 1 calc R U
C19 C 0.7851(3) -0.02398(18) 0.61544(17) 0.0408(4) Uani 1 1 d . .
H19A H 0.7531 -0.0823 0.5424 0.049 Uiso 1 1 calc R U
H19B H 0.6873 -0.0447 0.6612 0.049 Uiso 1 1 calc R U
H19C H 0.8759 -0.0378 0.6599 0.049 Uiso 1 1 calc R U
C20 C 1.0854(2) 1.49401(16) 0.16913(16) 0.0334(4) Uani 1 1 d . .
H20A H 1.0153 1.5428 0.1911 0.040 Uiso 1 1 calc R U
H20B H 1.0874 1.4864 0.0843 0.040 Uiso 1 1 calc R U
H20C H 1.2004 1.5418 0.2055 0.040 Uiso 1 1 calc R U
C21 C 1.13380(19) 1.30840(16) 0.25462(15) 0.0313(4) Uani 1 1 d . .
H21A H 1.1418 1.2418 0.1966 0.038 Uiso 1 1 calc R U
H21B H 1.0944 1.2669 0.3256 0.038 Uiso 1 1 calc R U
H21C H 1.2450 1.3805 0.2727 0.038 Uiso 1 1 calc R U
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 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
C9 O1 C10 117.75(11) .
C3 N2 C2 119.80(13) .
C7 N3 C21 120.21(12) .
C7 N3 C20 120.54(13) .
C21 N3 C20 117.37(12) .
N1 C1 C2 176.87(16) .
C2 C2 N2 120.68(17) 2_575
C2 C2 C1 117.59(16) 2_575
N2 C2 C1 121.72(13) .
N2 C3 C4 121.65(14) .
N2 C3 H3 119.2 .
C4 C3 H3 119.2 .
C5 C4 C9 117.17(13) .
C5 C4 C3 121.99(13) .
C9 C4 C3 120.84(13) .
C6 C5 C4 122.58(14) .
C6 C5 H5 118.7 .
C4 C5 H5 118.7 .
C5 C6 C7 120.07(14) .
C5 C6 H6 120.0 .
C7 C6 H6 120.0 .
N3 C7 C8 120.34(13) .
N3 C7 C6 121.55(13) .
C8 C7 C6 118.10(13) .
C9 C8 C7 120.89(13) .
C9 C8 H8 119.6 .
C7 C8 H8 119.6 .
O1 C9 C8 123.11(13) .
O1 C9 C4 115.74(12) .
C8 C9 C4 121.15(13) .
O1 C10 C11 108.73(11) .
O1 C10 H10A 109.9 .
C11 C10 H10A 109.9 .
O1 C10 H10B 109.9 .
C11 C10 H10B 109.9 .
H10A C10 H10B 108.3 .
C10 C11 C12 109.91(12) .
C10 C11 H11A 109.7 .
C12 C11 H11A 109.7 .
C10 C11 H11B 109.7 .
C12 C11 H11B 109.7 .
H11A C11 H11B 108.2 .
C13 C12 C11 114.89(12) .
C13 C12 H12A 108.5 .
C11 C12 H12A 108.5 .
C13 C12 H12B 108.5 .
C11 C12 H12B 108.5 .
H12A C12 H12B 107.5 .
C12 C13 C14 111.60(12) .
C12 C13 H13A 109.3 .
C14 C13 H13A 109.3 .
C12 C13 H13B 109.3 .
C14 C13 H13B 109.3 .
H13A C13 H13B 108.0 .
C15 C14 C13 114.96(12) .
C15 C14 H14A 108.5 .
C13 C14 H14A 108.5 .
C15 C14 H14B 108.5 .
C13 C14 H14B 108.5 .
H14A C14 H14B 107.5 .
C14 C15 C16 111.69(12) .
C14 C15 H15A 109.3 .
C16 C15 H15A 109.3 .
C14 C15 H15B 109.3 .
C16 C15 H15B 109.3 .
H15A C15 H15B 107.9 .
C17 C16 C15 114.90(12) .
C17 C16 H16A 108.5 .
C15 C16 H16A 108.5 .
C17 C16 H16B 108.5 .
C15 C16 H16B 108.5 .
H16A C16 H16B 107.5 .
C18 C17 C16 112.58(13) .
C18 C17 H17A 109.1 .
C16 C17 H17A 109.1 .
C18 C17 H17B 109.1 .
C16 C17 H17B 109.1 .
H17A C17 H17B 107.8 .
C17 C18 C19 113.96(14) .
C17 C18 H18A 108.8 .
C19 C18 H18A 108.8 .
C17 C18 H18B 108.8 .
C19 C18 H18B 108.8 .
H18A C18 H18B 107.7 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C18 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
N3 C20 H20A 109.5 .
N3 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
N3 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
N3 C21 H21A 109.5 .
N3 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
N3 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.3643(17) .
O1 C10 1.4352(17) .
N1 C1 1.148(2) .
N2 C3 1.295(2) .
N2 C2 1.3808(19) .
N3 C7 1.3642(19) .
N3 C21 1.452(2) .
N3 C20 1.4566(19) .
C1 C2 1.449(2) .
C2 C2 1.371(3) 2_575
C3 C4 1.438(2) .
C3 H3 0.9500 .
C4 C5 1.406(2) .
C4 C9 1.415(2) .
C5 C6 1.373(2) .
C5 H5 0.9500 .
C6 C7 1.420(2) .
C6 H6 0.9500 .
C7 C8 1.412(2) .
C8 C9 1.385(2) .
C8 H8 0.9500 .
C10 C11 1.5096(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.528(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.523(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.524(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.523(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.524(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.523(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C18 1.518(2) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.520(2) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 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_4
C3 N2 C2 C2 -178.62(17) 2_575
C3 N2 C2 C1 3.0(2) .
C2 N2 C3 C4 -179.76(13) .
N2 C3 C4 C5 -3.9(2) .
N2 C3 C4 C9 176.47(14) .
C9 C4 C5 C6 -0.5(2) .
C3 C4 C5 C6 179.92(14) .
C4 C5 C6 C7 -1.1(2) .
C21 N3 C7 C8 7.4(2) .
C20 N3 C7 C8 171.44(14) .
C21 N3 C7 C6 -173.32(14) .
C20 N3 C7 C6 -9.3(2) .
C5 C6 C7 N3 -177.36(14) .
C5 C6 C7 C8 1.9(2) .
N3 C7 C8 C9 178.04(14) .
C6 C7 C8 C9 -1.2(2) .
C10 O1 C9 C8 -4.4(2) .
C10 O1 C9 C4 176.02(13) .
C7 C8 C9 O1 -179.83(13) .
C7 C8 C9 C4 -0.3(2) .
C5 C4 C9 O1 -179.29(12) .
C3 C4 C9 O1 0.3(2) .
C5 C4 C9 C8 1.2(2) .
C3 C4 C9 C8 -179.22(14) .
C9 O1 C10 C11 -177.39(12) .
O1 C10 C11 C12 -174.05(12) .
C10 C11 C12 C13 178.24(13) .
C11 C12 C13 C14 -177.82(13) .
C12 C13 C14 C15 179.83(13) .
C13 C14 C15 C16 -179.88(13) .
C14 C15 C16 C17 -178.78(13) .
C15 C16 C17 C18 178.94(14) .
C16 C17 C18 C19 -179.44(15) .
