#------------------------------------------------------------------------------
#$Date: 2022-11-28 10:21:35 +0200 (Mon, 28 Nov 2022) $
#$Revision: 279584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106263.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_8106263
loop_
_publ_author_name
'Wang, Wan-Wan'
'Zong, Hai-Tao'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of ethyl
 5-formyl-3,4-dimethylpyrrole-2-carboxylate--1-(propan-2-ylidene)thiosemicarbazide
 (1/1), C14H22N4O3S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              689
_journal_page_last               690
_journal_paper_doi               10.1515/ncrs-2018-0015
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C14 H22 N4 O3 S'
_chemical_formula_weight         326.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                81.822(2)
_cell_angle_beta                 89.151(2)
_cell_angle_gamma                70.735(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9906(9)
_cell_length_b                   8.0075(11)
_cell_length_c                   16.057(2)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.12
_cell_volume                     839.37(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4412
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.282
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0444
_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)+(0.0601P)²+0.3282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2341
_reflns_number_total             2938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0015_suppl.cif
_cod_data_source_block           z
_cod_original_cell_volume        839.4(2)
_cod_database_code               8106263
_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   0.959
_shelx_estimated_absorpt_t_max   0.967
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.6332(3) 0.72001(19) -0.14989(9) 0.0554(4) Uani 1 1 d . . . . .
O3 O 1.0119(3) -0.0173(2) 0.11150(10) 0.0681(5) Uani 1 1 d . . . . .
N1 N 0.8341(3) 0.3153(2) -0.00592(10) 0.0403(4) Uani 1 1 d . . . . .
H1 H 0.866051 0.228980 -0.035393 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8624(3) 0.2976(3) 0.07912(12) 0.0417(5) Uani 1 1 d . . . . .
O1 O 0.7242(3) 0.4375(2) -0.17547(10) 0.0720(6) Uani 1 1 d . . . . .
C1 C 0.7474(3) 0.4913(2) -0.03652(12) 0.0391(5) Uani 1 1 d . . . . .
C8 C 0.6252(4) 0.7886(3) 0.02710(15) 0.0553(6) Uani 1 1 d . . . . .
H8A H 0.729003 0.837939 0.037466 0.083 Uiso 1 1 calc R U . . .
H8B H 0.525566 0.813641 0.069515 0.083 Uiso 1 1 calc R U . . .
H8C H 0.561693 0.841346 -0.027313 0.083 Uiso 1 1 calc R U . . .
C3 C 0.7901(3) 0.4678(3) 0.10292(12) 0.0430(5) Uani 1 1 d . . . . .
C5 C 0.7020(3) 0.5434(3) -0.12715(13) 0.0458(5) Uani 1 1 d . . . . .
C2 C 0.7177(3) 0.5904(3) 0.02966(12) 0.0410(5) Uani 1 1 d . . . . .
C10 C 0.9512(4) 0.1308(3) 0.13234(13) 0.0540(6) Uani 1 1 d . . . . .
H10 H 0.963968 0.136369 0.189369 0.065 Uiso 1 1 calc R U . . .
C9 C 0.7889(4) 0.5149(3) 0.19010(14) 0.0607(7) Uani 1 1 d . . . . .
H9A H 0.854398 0.408651 0.228885 0.091 Uiso 1 1 calc R U . . .
H9B H 0.651507 0.567555 0.205952 0.091 Uiso 1 1 calc R U . . .
H9C H 0.860194 0.598555 0.191259 0.091 Uiso 1 1 calc R U . . .
C6 C 0.5835(5) 0.7851(3) -0.23865(15) 0.0695(8) Uani 1 1 d . . . . .
H6A H 0.482558 0.739195 -0.258090 0.083 Uiso 1 1 calc R U . . .
H6B H 0.703533 0.746150 -0.271503 0.083 Uiso 1 1 calc R U . . .
C7 C 0.5027(5) 0.9842(4) -0.24833(17) 0.0790(9) Uani 1 1 d . . . . .
H7A H 0.379470 1.021278 -0.218333 0.119 Uiso 1 1 calc R U . . .
H7B H 0.475701 1.031844 -0.306908 0.119 Uiso 1 1 calc R U . . .
H7C H 0.600834 1.027718 -0.225975 0.119 Uiso 1 1 calc R U . . .
N3 N 0.8688(3) 0.2703(2) -0.44204(10) 0.0473(5) Uani 1 1 d . . . . .
H3 H 0.889395 0.232314 -0.489961 0.057 Uiso 1 1 calc R U . . .
N4 N 0.7759(3) 0.4510(2) -0.43706(11) 0.0464(4) Uani 1 1 d . . . . .
C11 C 0.9257(3) 0.1561(3) -0.36944(12) 0.0462(5) Uani 1 1 d . . . . .
N2 N 0.8885(3) 0.2275(3) -0.29905(11) 0.0597(6) Uani 1 1 d . . . . .
H2A H 0.830903 0.341024 -0.301183 0.072 Uiso 1 1 calc R U . . .
H2B H 0.921847 0.160435 -0.251145 0.072 Uiso 1 1 calc R U . . .
C12 C 0.7206(3) 0.5610(3) -0.50505(13) 0.0458(5) Uani 1 1 d . . . . .
C14 C 0.6217(4) 0.7537(3) -0.49573(16) 0.0602(6) Uani 1 1 d . . . . .
H14A H 0.607477 0.765180 -0.437065 0.090 Uiso 1 1 calc R U . . .
H14B H 0.490327 0.798036 -0.523586 0.090 Uiso 1 1 calc R U . . .
H14C H 0.703962 0.821470 -0.520562 0.090 Uiso 1 1 calc R U . . .
S1 S 1.03937(12) -0.06446(8) -0.37095(4) 0.0675(3) Uani 1 1 d . . . . .
C13 C 0.7457(4) 0.5155(3) -0.59216(14) 0.0598(6) Uani 1 1 d . . . . .
H13A H 0.886266 0.453851 -0.600452 0.090 Uiso 1 1 calc R U . . .
H13B H 0.699340 0.623267 -0.631883 0.090 Uiso 1 1 calc R U . . .
H13C H 0.667730 0.440024 -0.600338 0.090 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
C5 O2 C6 117.01(17) . .
C1 N1 C4 108.93(16) . .
C1 N1 H1 125.5 . .
C4 N1 H1 125.5 . .
N1 C4 C3 108.04(17) . .
N1 C4 C10 124.43(18) . .
C3 C4 C10 127.53(19) . .
N1 C1 C2 109.08(17) . .
N1 C1 C5 118.83(17) . .
C2 C1 C5 132.08(18) . .
C2 C8 H8A 109.5 . .
C2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C4 C3 C2 107.39(17) . .
C4 C3 C9 127.29(19) . .
C2 C3 C9 125.32(18) . .
O1 C5 O2 123.86(19) . .
O1 C5 C1 123.30(19) . .
O2 C5 C1 112.84(17) . .
C1 C2 C3 106.55(17) . .
C1 C2 C8 128.59(18) . .
C3 C2 C8 124.85(18) . .
O3 C10 C4 127.3(2) . .
O3 C10 H10 116.3 . .
C4 C10 H10 116.3 . .
C3 C9 H9A 109.5 . .
C3 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C3 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O2 C6 C7 107.4(2) . .
O2 C6 H6A 110.2 . .
C7 C6 H6A 110.2 . .
O2 C6 H6B 110.2 . .
C7 C6 H6B 110.2 . .
H6A C6 H6B 108.5 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C11 N3 N4 118.08(17) . .
C11 N3 H3 121.0 . .
N4 N3 H3 121.0 . .
C12 N4 N3 118.97(17) . .
N2 C11 N3 116.41(19) . .
N2 C11 S1 123.07(17) . .
N3 C11 S1 120.52(15) . .
C11 N2 H2A 120.0 . .
C11 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
N4 C12 C13 126.2(2) . .
N4 C12 C14 116.54(19) . .
C13 C12 C14 117.26(19) . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C5 1.332(2) .
O2 C6 1.452(3) .
O3 C10 1.215(3) .
N1 C1 1.358(2) .
N1 C4 1.363(2) .
N1 H1 0.8600 .
C4 C3 1.395(3) .
C4 C10 1.429(3) .
O1 C5 1.201(2) .
C1 C2 1.388(3) .
C1 C5 1.465(3) .
C8 C2 1.498(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C3 C2 1.402(3) .
C3 C9 1.500(3) .
C10 H10 0.9300 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C6 C7 1.491(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
N3 C11 1.351(3) .
N3 N4 1.391(2) .
N3 H3 0.8600 .
N4 C12 1.277(3) .
C11 N2 1.323(3) .
C11 S1 1.684(2) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C12 C13 1.488(3) .
C12 C14 1.497(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86 2.17 3.021(2) 171.8 2_755 yes
N3 H3 S1 0.86 2.72 3.5774(18) 171.7 2_754 yes
N2 H2A O1 0.86 2.29 2.773(2) 115.6 . yes
N2 H2B O3 0.86 2.35 3.199(2) 171.2 2_755 yes
C10 H10 S1 0.93 2.89 3.791(2) 163.0 2_755 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C4 C3 0.4(2) . . . .
C1 N1 C4 C10 -179.7(2) . . . .
C4 N1 C1 C2 -0.2(2) . . . .
C4 N1 C1 C5 -179.92(19) . . . .
N1 C4 C3 C2 -0.4(2) . . . .
C10 C4 C3 C2 179.7(2) . . . .
N1 C4 C3 C9 179.9(2) . . . .
C10 C4 C3 C9 0.0(4) . . . .
C6 O2 C5 O1 -0.1(4) . . . .
C6 O2 C5 C1 -179.9(2) . . . .
N1 C1 C5 O1 5.5(3) . . . .
C2 C1 C5 O1 -174.1(2) . . . .
N1 C1 C5 O2 -174.73(18) . . . .
C2 C1 C5 O2 5.7(3) . . . .
N1 C1 C2 C3 0.0(2) . . . .
C5 C1 C2 C3 179.6(2) . . . .
N1 C1 C2 C8 -179.3(2) . . . .
C5 C1 C2 C8 0.4(4) . . . .
C4 C3 C2 C1 0.2(2) . . . .
C9 C3 C2 C1 179.9(2) . . . .
C4 C3 C2 C8 179.5(2) . . . .
C9 C3 C2 C8 -0.8(4) . . . .
N1 C4 C10 O3 -0.8(4) . . . .
C3 C4 C10 O3 179.1(3) . . . .
C5 O2 C6 C7 177.8(2) . . . .
C11 N3 N4 C12 -179.8(2) . . . .
N4 N3 C11 N2 -0.4(3) . . . .
N4 N3 C11 S1 -179.89(15) . . . .
N3 N4 C12 C13 -0.1(3) . . . .
N3 N4 C12 C14 -179.92(19) . . . .
