#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:55:19 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/26/4032691.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_4032691
loop_
_publ_author_name
'Klikar, Milan'
'le Poul, Pascal'
'R°užička, Aleš'
'Pytela, Oldřich'
'Barsella, Alberto'
'Dorkenoo, Kokou D.'
'Robin-le Guen, Françoise'
'Bureš, Filip'
'Achelle, Sylvain'
_publ_section_title
;
 Dipolar NLO Chromophores Bearing Diazine Rings as π-Conjugated Linkers.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9435
_journal_page_last               9451
_journal_paper_doi               10.1021/acs.joc.7b01442
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C36.5 H24 Cl N O2 S2'
_chemical_formula_weight         608.14
_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   mixed
_audit_creation_method           'APEX3 v2016.5-0'
_cell_angle_alpha                99.293(2)
_cell_angle_beta                 91.403(2)
_cell_angle_gamma                109.660(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7933(5)
_cell_length_b                   9.9953(5)
_cell_length_c                   15.9261(8)
_cell_measurement_reflns_used    90854
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1443.59(13)
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            90854
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         2.200
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.091
_refine_diff_density_max         1.087
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6631
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0538
_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/[σ²(Fo²)+(0.0426P)²+1.9457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4939
_reflns_number_total             6631
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01442_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4032691.cif.'
_cod_original_formula_sum        'C36.50 H24 Cl N O2 S2'
_cod_database_code               4032691
_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   0.922
_shelx_estimated_absorpt_t_max   0.972
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.947
;
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
_atom_site_refinement_flags_occupancy
S1 S -0.46989(7) -0.81783(7) 0.35048(4) 0.02545(16) Uani 1 1 d . . .
C1 C -0.0611(2) -0.4018(2) 0.44141(14) 0.0158(5) Uani 1 1 d . . .
O1 O 0.03446(19) -0.5449(2) 0.33801(12) 0.0305(4) Uani 1 1 d . . .
Cl1 Cl 0.38912(12) 0.56132(11) 1.03150(7) 0.0665(3) Uani 1 1 d . . .
N1 N 0.9762(2) 1.0026(2) 0.86388(13) 0.0194(4) Uani 1 1 d . . .
S2 S 0.48880(6) 0.35900(6) 0.67886(4) 0.01876(14) Uani 1 1 d . . .
C2 C -0.0662(2) -0.5315(3) 0.37735(15) 0.0180(5) Uani 1 1 d . . .
O2 O -0.24874(17) -0.35267(18) 0.52716(11) 0.0220(4) Uani 1 1 d . . .
C7 C -0.4412(3) -0.6628(3) 0.42338(16) 0.0226(5) Uani 1 1 d . . .
H7 H -0.5133 -0.6408 0.4559 0.027 Uiso 1 1 calc R U .
C6 C -0.2930(3) -0.7675(3) 0.32485(16) 0.0222(5) Uani 1 1 d . . .
H6 H -0.2549 -0.8232 0.2843 0.027 Uiso 1 1 calc R U .
C5 C -0.2085(2) -0.4306(2) 0.47407(14) 0.0157(5) Uani 1 1 d . . .
H5 H 0.605(6) 0.665(3) 1.012(4) 0.044(18) Uiso 0.5 1 d D . P
C4 C -0.2988(2) -0.5756(3) 0.42757(14) 0.0167(5) Uani 1 1 d . . .
C3 C -0.2156(2) -0.6355(2) 0.37142(14) 0.0169(5) Uani 1 1 d . . .
H3 H 0.596(6) 0.576(6) 1.0825(16) 0.032(16) Uiso 0.5 1 d D . P
C8 C 0.0645(2) -0.2876(2) 0.45529(14) 0.0163(5) Uani 1 1 d . . .
H8 H 0.1370 -0.3032 0.4205 0.020 Uiso 1 1 calc R U .
C9 C 0.1153(2) -0.1473(2) 0.51037(14) 0.0158(5) Uani 1 1 d . . .
C10 C 0.0367(2) -0.0984(3) 0.57388(15) 0.0179(5) Uani 1 1 d . . .
H10 H -0.0592 -0.1579 0.5812 0.021 Uiso 1 1 calc R U .
C11 C 0.0981(2) 0.0349(2) 0.62535(15) 0.0182(5) Uani 1 1 d . . .
H11 H 0.0436 0.0656 0.6681 0.022 Uiso 1 1 calc R U .
C13 C 0.3163(3) 0.0785(3) 0.55256(15) 0.0196(5) Uani 1 1 d . . .
H13 H 0.4114 0.1389 0.5444 0.023 Uiso 1 1 calc R U .
C12 C 0.2390(2) 0.1267(2) 0.61626(14) 0.0153(5) Uani 1 1 d . . .
C14 C 0.2558(3) -0.0553(3) 0.50163(15) 0.0196(5) Uani 1 1 d . . .
H14 H 0.3110 -0.0861 0.4594 0.023 Uiso 1 1 calc R U .
C15 C 0.3031(2) 0.2675(2) 0.67128(14) 0.0158(5) Uani 1 1 d . . .
C16 C 0.2370(2) 0.3464(2) 0.72354(14) 0.0168(5) Uani 1 1 d . . .
H16 H 0.1351 0.3148 0.7288 0.020 Uiso 1 1 calc R U .
C17 C 0.3353(2) 0.4790(2) 0.76860(14) 0.0160(5) Uani 1 1 d . . .
H17 H 0.3059 0.5451 0.8072 0.019 Uiso 1 1 calc R U .
C18 C 0.4767(2) 0.5028(2) 0.75126(14) 0.0148(5) Uani 1 1 d . . .
C19 C 0.6070(2) 0.6283(2) 0.78266(14) 0.0147(5) Uani 1 1 d . . .
C20 C 0.6058(3) 0.7314(3) 0.85294(16) 0.0213(5) Uani 1 1 d . . .
H20 H 0.5200 0.7180 0.8821 0.026 Uiso 1 1 calc R U .
C21 C 0.7275(3) 0.8528(3) 0.88085(16) 0.0223(5) Uani 1 1 d . . .
H21 H 0.7252 0.9214 0.9291 0.027 Uiso 1 1 calc R U .
C22 C 0.8531(2) 0.8739(2) 0.83801(15) 0.0175(5) Uani 1 1 d . . .
C23 C 0.8569(2) 0.7713(3) 0.76961(15) 0.0203(5) Uani 1 1 d . . .
H23 H 0.9433 0.7842 0.7412 0.024 Uiso 1 1 calc R U .
C24 C 0.7351(3) 0.6499(3) 0.74228(15) 0.0202(5) Uani 1 1 d . . .
H24 H 0.7390 0.5801 0.6951 0.024 Uiso 1 1 calc R U .
C25 C 0.9597(2) 1.1364(2) 0.85784(15) 0.0183(5) Uani 1 1 d . . .
C26 C 0.8547(3) 1.1431(3) 0.79961(17) 0.0265(6) Uani 1 1 d . . .
H26 H 0.7942 1.0575 0.7631 0.032 Uiso 1 1 calc R U .
C27 C 0.8382(3) 1.2740(3) 0.7947(2) 0.0360(7) Uani 1 1 d . . .
H27 H 0.7652 1.2768 0.7553 0.043 Uiso 1 1 calc R U .
C28 C 0.9263(3) 1.4005(3) 0.8462(2) 0.0365(7) Uani 1 1 d . . .
H28 H 0.9155 1.4901 0.8418 0.044 Uiso 1 1 calc R U .
C29 C 1.0298(3) 1.3943(3) 0.90375(18) 0.0297(6) Uani 1 1 d . . .
H29 H 1.0908 1.4807 0.9395 0.036 Uiso 1 1 calc R U .
C30 C 1.0469(3) 1.2640(3) 0.91067(16) 0.0215(5) Uani 1 1 d . . .
H30 H 1.1182 1.2616 0.9514 0.026 Uiso 1 1 calc R U .
C31 C 1.1144(2) 0.9896(2) 0.87590(14) 0.0169(5) Uani 1 1 d . . .
C32 C 1.2398(3) 1.0854(3) 0.85153(16) 0.0217(5) Uani 1 1 d . . .
H32 H 1.2341 1.1629 0.8257 0.026 Uiso 1 1 calc R U .
C33 C 1.3733(3) 1.0687(3) 0.86462(18) 0.0309(6) Uani 1 1 d . U .
H33 H 1.4582 1.1352 0.8477 0.037 Uiso 1 1 calc R U .
C34 C 1.3843(3) 0.9575(3) 0.90167(19) 0.0360(7) Uani 1 1 d . U .
H34 H 1.4763 0.9475 0.9111 0.043 Uiso 1 1 calc R U .
C35 C 1.2600(3) 0.8606(3) 0.92493(18) 0.0344(7) Uani 1 1 d . U .
H35 H 1.2665 0.7824 0.9498 0.041 Uiso 1 1 calc R U .
C36 C 1.1258(3) 0.8756(3) 0.91253(16) 0.0248(5) Uani 1 1 d . . .
H36 H 1.0412 0.8081 0.9290 0.030 Uiso 1 1 calc R U .
C37 C 0.5608(7) 0.5773(6) 1.0288(4) 0.0376(14) Uani 0.5 1 d D . P
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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 '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
C6 S1 C7 93.82(12) . .
C8 C1 C5 134.2(2) . .
C8 C1 C2 117.8(2) . .
C5 C1 C2 107.98(19) . .
C37 Cl1 C37 59.8(3) . 2_667
C31 N1 C25 122.15(19) . .
C31 N1 C22 118.38(19) . .
C25 N1 C22 117.95(19) . .
C15 S2 C18 92.78(11) . .
O1 C2 C3 127.7(2) . .
O1 C2 C1 125.7(2) . .
C3 C2 C1 106.66(19) . .
C4 C7 S1 109.72(19) . .
C4 C7 H7 125.1 . .
S1 C7 H7 125.1 . .
C3 C6 S1 109.60(19) . .
C3 C6 H6 125.2 . .
S1 C6 H6 125.2 . .
O2 C5 C4 126.2(2) . .
O2 C5 C1 128.3(2) . .
C4 C5 C1 105.48(18) . .
C7 C4 C3 113.0(2) . .
C7 C4 C5 136.2(2) . .
C3 C4 C5 110.7(2) . .
C6 C3 C4 113.8(2) . .
C6 C3 C2 137.0(2) . .
C4 C3 C2 109.1(2) . .
C1 C8 C9 135.5(2) . .
C1 C8 H8 112.3 . .
C9 C8 H8 112.3 . .
C14 C9 C10 117.6(2) . .
C14 C9 C8 117.1(2) . .
C10 C9 C8 125.2(2) . .
C11 C10 C9 120.4(2) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 121.6(2) . .
C10 C11 H11 119.2 . .
C12 C11 H11 119.2 . .
C14 C13 C12 120.7(2) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C12 C11 117.8(2) . .
C13 C12 C15 121.0(2) . .
C11 C12 C15 121.2(2) . .
C13 C14 C9 121.8(2) . .
C13 C14 H14 119.1 . .
C9 C14 H14 119.1 . .
C16 C15 C12 129.4(2) . .
C16 C15 S2 109.99(17) . .
C12 C15 S2 120.56(17) . .
C15 C16 C17 113.4(2) . .
C15 C16 H16 123.3 . .
C17 C16 H16 123.3 . .
C18 C17 C16 113.5(2) . .
C18 C17 H17 123.3 . .
C16 C17 H17 123.3 . .
C17 C18 C19 129.4(2) . .
C17 C18 S2 110.30(17) . .
C19 C18 S2 120.26(16) . .
C24 C19 C20 118.0(2) . .
C24 C19 C18 120.9(2) . .
C20 C19 C18 121.1(2) . .
C21 C20 C19 121.1(2) . .
C21 C20 H20 119.4 . .
C19 C20 H20 119.4 . .
C20 C21 C22 119.8(2) . .
C20 C21 H21 120.1 . .
C22 C21 H21 120.1 . .
C23 C22 C21 119.7(2) . .
C23 C22 N1 120.4(2) . .
C21 C22 N1 119.9(2) . .
C22 C23 C24 120.2(2) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
C23 C24 C19 121.1(2) . .
C23 C24 H24 119.4 . .
C19 C24 H24 119.4 . .
C26 C25 C30 118.6(2) . .
C26 C25 N1 120.6(2) . .
C30 C25 N1 120.8(2) . .
C27 C26 C25 120.3(3) . .
C27 C26 H26 119.9 . .
C25 C26 H26 119.9 . .
C28 C27 C26 121.0(3) . .
C28 C27 H27 119.5 . .
C26 C27 H27 119.5 . .
C29 C28 C27 118.8(3) . .
C29 C28 H28 120.6 . .
C27 C28 H28 120.6 . .
C28 C29 C30 121.1(3) . .
C28 C29 H29 119.4 . .
C30 C29 H29 119.4 . .
C29 C30 C25 120.1(2) . .
C29 C30 H30 119.9 . .
C25 C30 H30 119.9 . .
C32 C31 C36 118.5(2) . .
C32 C31 N1 122.3(2) . .
C36 C31 N1 119.2(2) . .
C33 C32 C31 120.4(2) . .
C33 C32 H32 119.8 . .
C31 C32 H32 119.8 . .
C34 C33 C32 120.9(3) . .
C34 C33 H33 119.5 . .
C32 C33 H33 119.5 . .
C33 C34 C35 119.0(2) . .
C33 C34 H34 120.5 . .
C35 C34 H34 120.5 . .
C34 C35 C36 120.9(3) . .
C34 C35 H35 119.6 . .
C36 C35 H35 119.6 . .
C35 C36 C31 120.2(3) . .
C35 C36 H36 119.9 . .
C31 C36 H36 119.9 . .
Cl1 C37 C37 64.0(4) . 2_667
Cl1 C37 Cl1 120.2(3) . 2_667
C37 C37 Cl1 56.2(4) 2_667 2_667
Cl1 C37 H5 105(4) . .
C37 C37 H5 129(4) 2_667 .
Cl1 C37 H5 112(4) 2_667 .
Cl1 C37 H3 108(4) . .
C37 C37 H3 119(4) 2_667 .
Cl1 C37 H3 100(4) 2_667 .
H5 C37 H3 112(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C6 1.713(3) .
S1 C7 1.714(3) .
C1 C8 1.351(3) .
C1 C5 1.498(3) .
C1 C2 1.501(3) .
O1 C2 1.214(3) .
Cl1 C37 1.636(7) .
Cl1 C37 1.771(7) 2_667
N1 C31 1.414(3) .
N1 C25 1.418(3) .
N1 C22 1.428(3) .
S2 C15 1.730(2) .
S2 C18 1.731(2) .
C2 C3 1.472(3) .
O2 C5 1.219(3) .
C7 C4 1.366(3) .
C7 H7 0.9500 .
C6 C3 1.360(3) .
C6 H6 0.9500 .
C5 C4 1.480(3) .
C4 C3 1.419(3) .
C8 C9 1.448(3) .
C8 H8 0.9500 .
C9 C14 1.399(3) .
C9 C10 1.409(3) .
C10 C11 1.376(3) .
C10 H10 0.9500 .
C11 C12 1.403(3) .
C11 H11 0.9500 .
C13 C14 1.375(3) .
C13 C12 1.399(3) .
C13 H13 0.9500 .
C12 C15 1.457(3) .
C14 H14 0.9500 .
C15 C16 1.375(3) .
C16 C17 1.414(3) .
C16 H16 0.9500 .
C17 C18 1.367(3) .
C17 H17 0.9500 .
C18 C19 1.463(3) .
C19 C24 1.391(3) .
C19 C20 1.397(3) .
C20 C21 1.384(3) .
C20 H20 0.9500 .
C21 C22 1.392(3) .
C21 H21 0.9500 .
C22 C23 1.380(3) .
C23 C24 1.384(3) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C25 C26 1.393(3) .
C25 C30 1.396(3) .
C26 C27 1.385(4) .
C26 H26 0.9500 .
C27 C28 1.383(4) .
C27 H27 0.9500 .
C28 C29 1.374(4) .
C28 H28 0.9500 .
C29 C30 1.389(3) .
C29 H29 0.9500 .
C30 H30 0.9500 .
C31 C32 1.388(3) .
C31 C36 1.395(3) .
C32 C33 1.387(3) .
C32 H32 0.9500 .
C33 C34 1.373(4) .
C33 H33 0.9500 .
C34 C35 1.379(4) .
C34 H34 0.9500 .
C35 C36 1.385(4) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C37 C37 1.702(11) 2_667
C37 Cl1 1.771(7) 2_667
C37 H5 0.920(10) .
C37 H3 0.916(10) .
