#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:51:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180452 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/21/7212181.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_7212181
loop_
_publ_author_name
'Krasowska, M.'
'Kochel, A.'
'Filarowski, A.'
_publ_section_title
;
 The conformational analysis of 2-hydroxyaryl Schiff thiosemicarbazones
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1955
_journal_paper_doi               10.1039/b921402j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C11 H15 N3 O S'
_chemical_formula_sum            'C11 H15 N3 O S'
_chemical_formula_weight         237.32
_chemical_name_common
;
1-(2-hydroxyphenyl)ethan-1-one N,N-dimethylthiosemicarbazone
;
_chemical_name_systematic
;
1-(2-hydroxyphenyl)ethan-1-one N,N-dimethylthiosemicarbazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.7290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.82700(10)
_cell_length_b                   7.29170(10)
_cell_length_c                   16.3656(3)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      3.06
_cell_volume                     1172.15(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, date)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, date)'
_computing_data_reduction        'CrysAlis RED '
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KM4-CCD
_diffrn_measurement_method       /w
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0102
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13582
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'CrysAlis RED, Oxford Diffraction'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_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     156
_refine_ls_number_reflns         2077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0299
_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)+(0.0476P)²+0.5442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                1853
_reflns_number_total             2077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b921402j.txt
_cod_data_source_block           olo33
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7212181
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.71747(3) 0.24930(5) 0.06065(2) 0.02243(14) Uani 1 1 d .
O1 O 0.44685(10) 0.43978(15) 0.17147(6) 0.0250(3) Uani 1 1 d .
H1O H 0.474(2) 0.390(3) 0.1280(13) 0.043(6) Uiso 1 1 d .
N1 N 0.42348(12) 0.28213(16) 0.03229(7) 0.0195(3) Uani 1 1 d .
N2 N 0.49207(12) 0.21961(17) -0.03361(8) 0.0204(3) Uani 1 1 d .
N3 N 0.68862(12) 0.13781(17) -0.09496(7) 0.0219(3) Uani 1 1 d .
C1 C 0.30905(14) 0.4318(2) 0.16993(9) 0.0212(3) Uani 1 1 d .
C2 C 0.22964(14) 0.37057(18) 0.10129(8) 0.0193(3) Uani 1 1 d .
C3 C 0.08713(14) 0.3697(2) 0.10871(9) 0.0233(3) Uani 1 1 d .
H3 H 0.0316 0.3298 0.0636 0.028 Uiso 1 1 calc R
C4 C 0.02556(15) 0.4251(2) 0.17950(9) 0.0263(3) Uani 1 1 d .
H4 H -0.0707 0.4214 0.1829 0.032 Uiso 1 1 calc R
C5 C 0.10530(16) 0.4862(2) 0.24551(9) 0.0270(3) Uani 1 1 d .
H5 H 0.0635 0.5252 0.2942 0.032 Uiso 1 1 calc R
C6 C 0.24535(15) 0.4903(2) 0.24047(9) 0.0255(3) Uani 1 1 d .
H6 H 0.2991 0.5335 0.2857 0.031 Uiso 1 1 calc R
C7 C 0.29332(14) 0.30649(18) 0.02586(8) 0.0191(3) Uani 1 1 d .
C8 C 0.21154(15) 0.2701(2) -0.05162(9) 0.0235(3) Uani 1 1 d .
H8A H 0.2584 0.3229 -0.0981 0.035 Uiso 1 1 calc R
H8B H 0.1213 0.3262 -0.0478 0.035 Uiso 1 1 calc R
H8C H 0.2016 0.1375 -0.0595 0.035 Uiso 1 1 calc R
C9 C 0.63069(14) 0.19989(19) -0.02719(8) 0.0191(3) Uani 1 1 d .
C10 C 0.83630(15) 0.1242(2) -0.10010(9) 0.0264(3) Uani 1 1 d .
H10A H 0.8708 0.2309 -0.1295 0.040 Uiso 1 1 calc R
H10B H 0.8597 0.0119 -0.1294 0.040 Uiso 1 1 calc R
H10C H 0.8776 0.1207 -0.0449 0.040 Uiso 1 1 calc R
C11 C 0.60772(16) 0.0896(2) -0.16866(9) 0.0278(4) Uani 1 1 d .
H11A H 0.5436 -0.0084 -0.1557 0.042 Uiso 1 1 calc R
H11B H 0.6684 0.0475 -0.2112 0.042 Uiso 1 1 calc R
H11C H 0.5571 0.1976 -0.1882 0.042 Uiso 1 1 calc R
H1N H 0.451(2) 0.198(3) -0.0761(14) 0.043(6) Uiso 1 1 d .
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
C1 O1 H1O 107.9(13)
C7 N1 N2 119.45(12)
N1 N2 C9 119.14(12)
N1 N2 H1N 120.0(15)
C9 N2 H1N 120.8(15)
C9 N3 C10 121.23(12)
C9 N3 C11 121.86(12)
C10 N3 C11 116.83(11)
O1 C1 C6 116.37(13)
O1 C1 C2 123.60(13)
C6 C1 C2 120.03(13)
C3 C2 C1 117.19(13)
C3 C2 C7 121.19(12)
C1 C2 C7 121.61(12)
C4 C3 C2 122.12(14)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 119.63(14)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.01(14)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C1 121.00(14)
C5 C6 H6 119.5
C1 C6 H6 119.5
N1 C7 C2 114.75(12)
N1 C7 C8 123.14(13)
C2 C7 C8 122.10(12)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 N2 114.70(12)
N3 C9 S1 124.08(11)
N2 C9 S1 121.22(11)
N3 C10 H10A 109.5
N3 C10 H10B 109.5
H10A C10 H10B 109.5
N3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 H11A 109.5
N3 C11 H11B 109.5
H11A C11 H11B 109.5
N3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.6881(14)
O1 C1 1.3549(17)
O1 H1O 0.85(2)
N1 C7 1.2925(18)
N1 N2 1.3673(17)
N2 C9 1.3706(19)
N2 H1N 0.81(2)
N3 C9 1.3405(19)
N3 C10 1.4596(18)
N3 C11 1.4671(18)
C1 C6 1.396(2)
C1 C2 1.420(2)
C2 C3 1.4094(19)
C2 C7 1.477(2)
C3 C4 1.383(2)
C3 H3 0.9500
C4 C5 1.389(2)
C4 H4 0.9500
C5 C6 1.382(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5041(19)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 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
C7 N1 N2 C9 177.85(12)
O1 C1 C2 C3 179.97(13)
C6 C1 C2 C3 -0.9(2)
O1 C1 C2 C7 1.3(2)
C6 C1 C2 C7 -179.56(13)
C1 C2 C3 C4 -0.2(2)
C7 C2 C3 C4 178.47(13)
C2 C3 C4 C5 0.9(2)
C3 C4 C5 C6 -0.4(2)
C4 C5 C6 C1 -0.7(2)
O1 C1 C6 C5 -179.43(14)
C2 C1 C6 C5 1.4(2)
N2 N1 C7 C2 178.77(12)
N2 N1 C7 C8 -0.3(2)
C3 C2 C7 N1 -167.70(13)
C1 C2 C7 N1 10.92(19)
C3 C2 C7 C8 11.4(2)
C1 C2 C7 C8 -169.99(13)
C10 N3 C9 N2 174.78(12)
C11 N3 C9 N2 -2.0(2)
C10 N3 C9 S1 -5.9(2)
C11 N3 C9 S1 177.38(11)
N1 N2 C9 N3 179.99(12)
N1 N2 C9 S1 0.62(18)
