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#$Date: 2022-02-04 21:55:01 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272723 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/11/7061129.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_7061129
loop_
_publ_author_name
'Selivanova, Galina'
'Skolyapova, Alexandrina'
'Wang, Jiaying'
'Karpova, Elena'
'Shundrina, Inna'
'Bagryanskaya, Irina'
'Amosov, Evgeny'
_publ_section_title
;
 Azo dyes containing 1,3,4-thiadiazole fragment: synthesis and properties
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1929
_journal_page_last               1942
_journal_paper_doi               10.1039/D1NJ05084B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C17 H23 N5 O S'
_chemical_formula_sum            'C17 H23 N5 O S'
_chemical_formula_weight         345.46
_chemical_name_systematic
;
 5-((4-(Di-n-butylamino)phenyl)diazenyl)-1,3,4-thiadiazole-2-carbaldehyde 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-10-11 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.645(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2794(7)
_cell_length_b                   20.596(3)
_cell_length_c                   16.720(2)
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.82
_cell_measurement_theta_min      2.33
_cell_volume                     1797.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15733
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.073
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_min         2.330
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0507
_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)+(0.0507P)²+0.8738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             3068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05084b2.cif
_cod_data_source_block           Ba_gas986
_cod_depositor_comments
'Adding full bibliography for 7061128--7061129.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061129
_shelx_shelxl_version_number     2014/7
_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   0.926
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.16354(15) 0.70484(4) 0.13230(5) 0.0447(3) Uani 1 1 d . . . . .
N1 N 0.0396(5) 0.59516(11) 0.07160(15) 0.0408(6) Uani 1 1 d . . . . .
N2 N 0.2022(5) 0.60529(11) 0.13616(14) 0.0384(6) Uani 1 1 d . . . . .
N5 N 1.0167(5) 0.43678(11) 0.22024(14) 0.0399(6) Uani 1 1 d . . . . .
N3 N -0.3358(5) 0.64125(12) 0.00259(15) 0.0477(7) Uani 1 1 d . . . . .
N4 N -0.5043(5) 0.69102(13) 0.00695(15) 0.0509(7) Uani 1 1 d . . . . .
O1 O -0.5517(5) 0.81577(12) 0.14747(17) 0.0724(7) Uani 1 1 d . . . . .
C7 C 0.3973(6) 0.56154(13) 0.15237(16) 0.0354(7) Uani 1 1 d . . . . .
C12 C 0.5738(6) 0.57268(14) 0.22250(17) 0.0400(7) Uani 1 1 d . . . . .
H12 H 0.5515 0.6096 0.2548 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7752(6) 0.53255(13) 0.24589(17) 0.0400(8) Uani 1 1 d . . . . .
H11 H 0.8895 0.5415 0.2941 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8169(5) 0.47689(13) 0.19851(17) 0.0349(7) Uani 1 1 d . . . . .
C8 C 0.4359(6) 0.50613(13) 0.10528(17) 0.0396(8) Uani 1 1 d . . . . .
H8 H 0.3195 0.4972 0.0575 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6375(6) 0.46564(13) 0.12772(17) 0.0384(7) Uani 1 1 d . . . . .
H9 H 0.6588 0.4288 0.0951 0.046 Uiso 1 1 calc R U . . .
C13' C 1.1951(6) 0.44654(14) 0.29524(18) 0.0434(8) Uani 1 1 d . . . . .
H13D H 1.2310 0.4936 0.3021 0.052 Uiso 1 1 calc R U . . .
H13C H 1.3588 0.4246 0.2901 0.052 Uiso 1 1 calc R U . . .
C14' C 1.0991(6) 0.42133(15) 0.37061(17) 0.0451(8) Uani 1 1 d . . . . .
H14D H 0.9276 0.4398 0.3734 0.054 Uiso 1 1 calc R U . . .
H14C H 1.0817 0.3735 0.3671 0.054 Uiso 1 1 calc R U . . .
C15' C 1.2783(7) 0.43889(16) 0.44654(19) 0.0573(9) Uani 1 1 d . . . . .
H15D H 1.2782 0.4866 0.4534 0.069 Uiso 1 1 calc R U . . .
H15C H 1.4544 0.4256 0.4402 0.069 Uiso 1 1 calc R U . . .
C16' C 1.2074(8) 0.4075(2) 0.5221(2) 0.0752(12) Uani 1 1 d . . . . .
H16F H 1.3303 0.4207 0.5692 0.113 Uiso 1 1 calc R U . . .
H16E H 1.0348 0.4212 0.5296 0.113 Uiso 1 1 calc R U . . .
H16D H 1.2111 0.3601 0.5165 0.113 Uiso 1 1 calc R U . . .
C13 C 1.0611(6) 0.37852(13) 0.17242(18) 0.0432(8) Uani 1 1 d . . . . .
H13B H 1.2437 0.3660 0.1853 0.052 Uiso 1 1 calc R U . . .
H13A H 1.0266 0.3897 0.1142 0.052 Uiso 1 1 calc R U . . .
C14 C 0.8958(6) 0.32028(13) 0.18764(18) 0.0442(8) Uani 1 1 d . . . . .
H14B H 0.9084 0.3130 0.2466 0.053 Uiso 1 1 calc R U . . .
H14A H 0.7145 0.3297 0.1661 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9793(6) 0.25950(14) 0.14790(19) 0.0511(8) Uani 1 1 d . . . . .
H15B H 1.1545 0.2477 0.1736 0.061 Uiso 1 1 calc R U . . .
H15A H 0.9848 0.2685 0.0900 0.061 Uiso 1 1 calc R U . . .
C16 C 0.7999(7) 0.20232(15) 0.1548(2) 0.0632(10) Uani 1 1 d . . . . .
H16C H 0.8612 0.1642 0.1283 0.095 Uiso 1 1 calc R U . . .
H16B H 0.7965 0.1926 0.2120 0.095 Uiso 1 1 calc R U . . .
H16A H 0.6267 0.2134 0.1285 0.095 Uiso 1 1 calc R U . . .
C2 C -0.1482(6) 0.64179(13) 0.06345(17) 0.0377(7) Uani 1 1 d . . . . .
C5 C -0.4391(6) 0.72760(14) 0.07131(19) 0.0433(8) Uani 1 1 d . . . . .
C6 C -0.5970(7) 0.78218(16) 0.0882(2) 0.0554(9) Uani 1 1 d . . . . .
H6 H -0.7448 0.7919 0.0503 0.067 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 0.0033 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'
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
_geom_angle_publ_flag
C5 S1 C2 86.01(15) . . ?
N2 N1 C2 110.5(2) . . ?
N1 N2 C7 116.5(2) . . ?
C10 N5 C13' 121.6(2) . . ?
C10 N5 C13 122.2(2) . . ?
C13' N5 C13 116.1(2) . . ?
C2 N3 N4 112.0(2) . . ?
C5 N4 N3 112.4(3) . . ?
N2 C7 C12 116.4(3) . . ?
N2 C7 C8 126.0(3) . . ?
C12 C7 C8 117.6(3) . . ?
C11 C12 C7 122.3(3) . . ?
C11 C12 H12 118.8 . . ?
C7 C12 H12 118.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N5 C10 C9 121.5(3) . . ?
N5 C10 C11 121.5(3) . . ?
C9 C10 C11 117.0(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
N5 C13' C14' 114.3(2) . . ?
N5 C13' H13D 108.7 . . ?
C14' C13' H13D 108.7 . . ?
N5 C13' H13C 108.7 . . ?
C14' C13' H13C 108.7 . . ?
H13D C13' H13C 107.6 . . ?
C15' C14' C13' 111.8(3) . . ?
C15' C14' H14D 109.3 . . ?
C13' C14' H14D 109.3 . . ?
C15' C14' H14C 109.3 . . ?
C13' C14' H14C 109.3 . . ?
H14D C14' H14C 107.9 . . ?
C14' C15' C16' 113.4(3) . . ?
C14' C15' H15D 108.9 . . ?
C16' C15' H15D 108.9 . . ?
C14' C15' H15C 108.9 . . ?
C16' C15' H15C 108.9 . . ?
H15D C15' H15C 107.7 . . ?
C15' C16' H16F 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16F C16' H16E 109.5 . . ?
C15' C16' H16D 109.5 . . ?
H16F C16' H16D 109.5 . . ?
H16E C16' H16D 109.5 . . ?
N5 C13 C14 114.0(2) . . ?
N5 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
N5 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
H13B C13 H13A 107.7 . . ?
C15 C14 C13 111.4(2) . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
H14B C14 H14A 108.0 . . ?
C14 C15 C16 112.3(3) . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
H15B C15 H15A 107.9 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
N3 C2 N1 121.5(3) . . ?
N3 C2 S1 114.5(2) . . ?
N1 C2 S1 124.0(2) . . ?
N4 C5 C6 121.0(3) . . ?
N4 C5 S1 115.1(2) . . ?
C6 C5 S1 123.9(3) . . ?
O1 C6 C5 123.8(3) . . ?
O1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.712(3) . ?
S1 C2 1.745(3) . ?
N1 N2 1.291(3) . ?
N1 C2 1.372(4) . ?
N2 C7 1.365(4) . ?
N5 C10 1.346(3) . ?
N5 C13' 1.464(4) . ?
N5 C13 1.480(4) . ?
N3 C2 1.309(4) . ?
N3 N4 1.366(3) . ?
N4 C5 1.316(4) . ?
O1 C6 1.202(4) . ?
C7 C12 1.402(4) . ?
C7 C8 1.418(4) . ?
C12 C11 1.357(4) . ?
C12 H12 0.9500 . ?
C11 C10 1.429(4) . ?
C11 H11 0.9500 . ?
C10 C9 1.419(4) . ?
C8 C9 1.360(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C13' C14' 1.519(4) . ?
C13' H13D 0.9900 . ?
C13' H13C 0.9900 . ?
C14' C15' 1.509(4) . ?
C14' H14D 0.9900 . ?
C14' H14C 0.9900 . ?
C15' C16' 1.516(5) . ?
C15' H15D 0.9900 . ?
C15' H15C 0.9900 . ?
C16' H16F 0.9800 . ?
C16' H16E 0.9800 . ?
C16' H16D 0.9800 . ?
C13 C14 1.527(4) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.514(4) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.527(4) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 0.9800 . ?
C5 C6 1.452(4) . ?
C6 H6 0.9500 . ?
