#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226060.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226060
loop_
_publ_author_name
'Mamari, Khalil'
'Zerzouf, Abdelfettah'
'Zouihri, Hafid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1-(1-Nonyl-2-oxoindolin-3-ylidene)thiosemicarbazide
;
_journal_coeditor_code           BT5264
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1332
_journal_paper_doi               10.1107/S160053681001651X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H26 N4 O S'
_chemical_formula_moiety         'C18 H26 N4 O S'
_chemical_formula_sum            'C18 H26 N4 O S'
_chemical_formula_weight         346.49
_chemical_name_systematic
;
1-(1-Nonyl-2-oxoindolin-3-ylidene)thiosemicarbazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5343(2)
_cell_length_b                   10.5921(2)
_cell_length_c                   15.6262(3)
_cell_measurement_reflns_used    6721
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      2.6
_cell_volume                     1898.90(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEXII diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26603
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5510
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.1904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                4006
_reflns_number_total             5510
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5264.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226060
_cod_database_fobs_code          2226060
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.76947(4) 0.88269(3) 0.65446(2) 0.02943(12) Uani d . 1 . .
O O1 0.86020(10) 0.77068(9) 0.93146(7) 0.0283(2) Uani d . 1 . .
N N1 0.73497(14) 1.11116(12) 0.71834(9) 0.0314(3) Uani d D 1 . .
N N2 0.78603(11) 0.95357(11) 0.81532(8) 0.0230(3) Uani d D 1 . .
N N3 0.79185(10) 1.03853(11) 0.88032(7) 0.0213(2) Uani d . 1 . .
N N4 0.90309(11) 0.86435(11) 1.06470(8) 0.0240(3) Uani d . 1 . .
C C1 0.76202(13) 0.99075(13) 0.73160(9) 0.0221(3) Uani d . 1 . .
C C2 0.82742(12) 0.99591(12) 0.95604(9) 0.0205(3) Uani d . 1 . .
C C3 0.84765(12) 1.07018(14) 1.03435(9) 0.0224(3) Uani d . 1 . .
C C4 0.83255(13) 1.19707(14) 1.05261(10) 0.0276(3) Uani d . 1 . .
H H4 0.8005 1.2539 1.0095 0.033 Uiso calc R 1 . .
C C5 0.86590(15) 1.23851(16) 1.13619(11) 0.0350(4) Uani d . 1 . .
H H5 0.8562 1.3248 1.1503 0.042 Uiso calc R 1 . .
C C6 0.91290(15) 1.15564(17) 1.19886(11) 0.0360(4) Uani d . 1 . .
H H6 0.9352 1.1865 1.2553 0.043 Uiso calc R 1 . .
C C7 0.92842(14) 1.02816(16) 1.18136(10) 0.0304(3) Uani d . 1 . .
H H7 0.9605 0.9716 1.2247 0.037 Uiso calc R 1 . .
C C8 0.89532(12) 0.98741(14) 1.09875(9) 0.0237(3) Uani d . 1 . .
C C9 0.86411(12) 0.86286(13) 0.97964(9) 0.0221(3) Uani d . 1 . .
C C10 0.95911(14) 0.75743(14) 1.11096(10) 0.0283(3) Uani d . 1 . .
H H10A 1.0326 0.7868 1.1432 0.034 Uiso calc R 1 . .
H H10B 0.9797 0.6939 1.0686 0.034 Uiso calc R 1 . .
C C11 0.88473(13) 0.69389(14) 1.17376(10) 0.0275(3) Uani d . 1 . .
H H11A 0.8186 0.6493 1.1415 0.033 Uiso calc R 1 . .
H H11B 0.8527 0.7585 1.2106 0.033 Uiso calc R 1 . .
C C12 0.95880(13) 0.60010(14) 1.22971(10) 0.0281(3) Uani d . 1 . .
H H12A 0.9906 0.5368 1.1918 0.034 Uiso calc R 1 . .
H H12B 1.0256 0.6459 1.2601 0.034 Uiso calc R 1 . .
C C13 0.89450(13) 0.53100(14) 1.29607(9) 0.0260(3) Uani d . 1 . .
H H13A 0.8586 0.5936 1.3323 0.031 Uiso calc R 1 . .
H H13B 0.8312 0.4795 1.2661 0.031 Uiso calc R 1 . .
C C14 0.97559(13) 0.44591(14) 1.35311(10) 0.0265(3) Uani d . 1 . .
H H14A 1.0372 0.4986 1.3841 0.032 Uiso calc R 1 . .
H H14B 1.0140 0.3865 1.3161 0.032 Uiso calc R 1 . .
C C15 0.91596(13) 0.36994(14) 1.41887(10) 0.0273(3) Uani d . 1 . .
H H15A 0.8789 0.4290 1.4570 0.033 Uiso calc R 1 . .
H H15B 0.8536 0.3179 1.3883 0.033 Uiso calc R 1 . .
C C16 0.99913(14) 0.28424(14) 1.47370(10) 0.0289(3) Uani d . 1 . .
H H16A 1.0606 0.3368 1.5050 0.035 Uiso calc R 1 . .
H H16B 1.0374 0.2268 1.4353 0.035 Uiso calc R 1 . .
C C17 0.94113(16) 0.20532(16) 1.53871(11) 0.0360(4) Uani d . 1 . .
H H17A 0.8791 0.1531 1.5078 0.043 Uiso calc R 1 . .
H H17B 0.9040 0.2624 1.5780 0.043 Uiso calc R 1 . .
C C18 1.0270(2) 0.11952(18) 1.59148(13) 0.0487(5) Uani d . 1 . .
H H18A 0.9857 0.0709 1.6322 0.073 Uiso calc R 1 . .
H H18B 1.0877 0.1709 1.6232 0.073 Uiso calc R 1 . .
H H18C 1.0628 0.0616 1.5530 0.073 Uiso calc R 1 . .
H H11 0.7307(17) 1.1607(16) 0.7620(9) 0.043(5) Uiso d D 1 . .
H H12 0.7173(18) 1.1345(19) 0.6657(7) 0.050(6) Uiso d D 1 . .
H H2 0.8141(15) 0.8786(11) 0.8267(12) 0.036(5) Uiso d D 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 H11 . . 119.5(14) ?
C1 N1 H12 . . 117.0(14) ?
H11 N1 H12 . . 123.4(19) ?
N3 N2 C1 . . 121.07(11) ?
N3 N2 H2 . . 117.7(13) ?
C1 N2 H2 . . 119.6(13) ?
C2 N3 N2 . . 116.17(11) ?
C9 N4 C8 . . 110.57(11) ?
C9 N4 C10 . . 124.13(12) ?
C8 N4 C10 . . 124.85(12) ?
N1 C1 N2 . . 116.64(13) ?
N1 C1 S1 . . 125.15(11) ?
N2 C1 S1 . . 118.21(10) ?
N3 C2 C3 . . 126.14(12) ?
N3 C2 C9 . . 127.25(12) ?
C3 C2 C9 . . 106.48(12) ?
C4 C3 C8 . . 120.37(13) ?
C4 C3 C2 . . 133.18(13) ?
C8 C3 C2 . . 106.41(12) ?
C3 C4 C5 . . 117.97(15) ?
C3 C4 H4 . . 121.0 ?
C5 C4 H4 . . 121.0 ?
C6 C5 C4 . . 120.90(15) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 121.67(15) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 117.33(15) ?
C8 C7 H7 . . 121.3 ?
C6 C7 H7 . . 121.3 ?
C7 C8 C3 . . 121.77(14) ?
C7 C8 N4 . . 128.26(14) ?
C3 C8 N4 . . 109.97(12) ?
O1 C9 N4 . . 126.53(13) ?
O1 C9 C2 . . 126.92(13) ?
N4 C9 C2 . . 106.55(12) ?
N4 C10 C11 . . 114.32(13) ?
N4 C10 H10A . . 108.7 ?
C11 C10 H10A . . 108.7 ?
N4 C10 H10B . . 108.7 ?
C11 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C10 C11 C12 . . 109.71(13) ?
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 . . 114.83(13) ?
C13 C12 H12A . . 108.6 ?
C11 C12 H12A . . 108.6 ?
C13 C12 H12B . . 108.6 ?
C11 C12 H12B . . 108.6 ?
H12A C12 H12B . . 107.5 ?
C14 C13 C12 . . 111.77(13) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C15 . . 114.55(13) ?
C13 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
C13 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C16 C15 C14 . . 113.15(13) ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15B . . 108.9 ?
C14 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.8 ?
C15 C16 C17 . . 114.13(13) ?
C15 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
C15 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C16 C17 C18 . . 112.53(15) ?
C16 C17 H17A . . 109.1 ?
C18 C17 H17A . . 109.1 ?
C16 C17 H17B . . 109.1 ?
C18 C17 H17B . . 109.1 ?
H17A C17 H17B . . 107.8 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.6710(14) ?
O1 C9 . 1.2309(17) ?
N1 C1 . 1.3242(19) ?
N1 H11 . 0.866(9) ?
N1 H12 . 0.862(9) ?
N2 N3 . 1.3534(16) ?
N2 C1 . 1.3669(18) ?
N2 H2 . 0.869(9) ?
N3 C2 . 1.2931(17) ?
N4 C9 . 1.3585(18) ?
N4 C8 . 1.4142(18) ?
N4 C10 . 1.4582(18) ?
C2 C3 . 1.4532(19) ?
C2 C9 . 1.5063(19) ?
C3 C4 . 1.389(2) ?
C3 C8 . 1.403(2) ?
C4 C5 . 1.394(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.384(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.393(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.377(2) ?
C7 H7 . 0.9500 ?
C10 C11 . 1.525(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.525(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.523(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.520(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.524(2) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.519(2) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.523(2) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.522(3) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H11 S1 2_656 0.870(10) 2.690(10) 3.4990(10) 156(2) no
N1 H12 O1 2_656 0.860(10) 2.220(10) 3.002(2) 152(2) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N2 N3 C2 . . . . -172.75(13) ?
N3 N2 C1 N1 . . . . -5.7(2) ?
N3 N2 C1 S1 . . . . 173.97(10) ?
N2 N3 C2 C3 . . . . 175.91(13) ?
N2 N3 C2 C9 . . . . 0.7(2) ?
N3 C2 C3 C4 . . . . 2.9(3) ?
C9 C2 C3 C4 . . . . 178.91(16) ?
N3 C2 C3 C8 . . . . -174.78(14) ?
C9 C2 C3 C8 . . . . 1.27(15) ?
C8 C3 C4 C5 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . -177.47(15) ?
C3 C4 C5 C6 . . . . 0.2(2) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
C5 C6 C7 C8 . . . . 0.2(2) ?
C6 C7 C8 C3 . . . . -0.1(2) ?
C6 C7 C8 N4 . . . . 179.29(15) ?
C4 C3 C8 C7 . . . . 0.1(2) ?
C2 C3 C8 C7 . . . . 178.06(14) ?
C4 C3 C8 N4 . . . . -179.43(13) ?
C2 C3 C8 N4 . . . . -1.42(16) ?
C9 N4 C8 C7 . . . . -178.41(15) ?
C10 N4 C8 C7 . . . . -5.9(2) ?
C9 N4 C8 C3 . . . . 1.03(17) ?
C10 N4 C8 C3 . . . . 173.50(13) ?
C8 N4 C9 O1 . . . . 179.53(14) ?
C10 N4 C9 O1 . . . . 7.0(2) ?
C8 N4 C9 C2 . . . . -0.18(16) ?
C10 N4 C9 C2 . . . . -172.71(13) ?
N3 C2 C9 O1 . . . . -4.4(2) ?
C3 C2 C9 O1 . . . . 179.61(14) ?
N3 C2 C9 N4 . . . . 175.31(14) ?
C3 C2 C9 N4 . . . . -0.69(15) ?
C9 N4 C10 C11 . . . . -108.71(16) ?
C8 N4 C10 C11 . . . . 79.81(18) ?
N4 C10 C11 C12 . . . . -169.81(13) ?
C10 C11 C12 C13 . . . . 179.42(13) ?
C11 C12 C13 C14 . . . . -176.25(13) ?
C12 C13 C14 C15 . . . . -177.78(13) ?
C13 C14 C15 C16 . . . . 178.98(13) ?
C14 C15 C16 C17 . . . . -178.83(13) ?
C15 C16 C17 C18 . . . . 179.22(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745036
