#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010163.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_2010163
loop_
_publ_author_name
'Yang, J.'
'Pandeya, S. N.'
'Dimmock, J. R.'
'Quail, J. W.'
_publ_section_title
;
 A novel bistetrahydronaphthyl thiosemicarbazone
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1828
_journal_page_last               1830
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C23 H25 N3 O2 S1'
_chemical_formula_sum            'C23 H25 N3 O2 S'
_chemical_formula_weight         407.53
_chemical_name_systematic
;
 2-[2-(2'-hydroxy-1'-oxo-1',2',3',4'-tetrahydronaphthyl)ethyl]-1,2,3,4-
 tetrahydronaphthylone thiosemicarbazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 99.54(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.492(4)
_cell_length_b                   13.048(3)
_cell_length_c                   15.595(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    289
_cell_measurement_theta_max      19.50
_cell_measurement_theta_min      7.00
_cell_volume                     2105.4(10)
_computing_cell_refinement       'Enraf-Nonius CAD-4 software'
_computing_data_collection       'Enraf-Nonius CAD-4 software'
_computing_data_reduction
'DATRD2 NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'ORTEP NRCVAX (Johnson, 1976)'
_computing_publication_material  'TABLES NRCVAX; UTILITY NRCVAX'
_computing_structure_refinement  'LSTSQ NRCVAX'
_computing_structure_solution    'SOLVER NRCVAX'
_diffrn_ambient_temperature      289
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4212
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.17
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      1.287
_exptl_crystal_density_method    'flotation in?'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864.74
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.47
_refine_ls_hydrogen_treatment    'H-atom parameters not refined'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_obs          0.049
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      '1/[\s^2^(F) + 0.00008F^2^]'
_refine_ls_wR_factor_all         0.050
_refine_ls_wR_factor_obs         0.050
_reflns_number_observed          2671
_reflns_number_total             3702
_reflns_observed_criterion       'Inet > 1.0\s(Inet)'
_[local]_cod_data_source_file    cr1128.cif
_[local]_cod_data_source_block   structure_1
_[local]_cod_cif_authors_sg_H-M  P21/a
_[local]_cod_chemical_formula_sum_orig 'C23 H25 N3 O2 S1'
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2105.2(11)
_cod_database_code               2010163
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2-x,1/2+y,-z
1/2+x,1/2-y,z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
S 0.0929(6) 0.0559(4) 0.1020(6) -0.0045(4) 0.0369(5) -0.0147(4) S
O1 0.0900(14) 0.0320(9) 0.1127(16) -0.0021(9) 0.0226(12) -0.0102(10) O
O2 0.0659(13) 0.0510(11) 0.1260(17) 0.069(10) 0.0097(12) 0.0148(11) O
N1 0.0468(12) 0.0342(11) 0.0686(13) 0.0010(9) 0.0029(11) 0.0053(10) N
N2 0.0639(14) 0.0313(10) 0.0689(13) -0.0014(10) 0.0094(12) 0.0009(10) N
N3 0.0718(16) 0.0354(11) 0.1118(19) -0.070(11) 0.0222(14) -0.012(12) N
C1 0.0412(14) 0.0336(12) 0.0590(15) 0.0038(10) -0.0038(12) 0.0088(11) C
C2 0.0466(14) 0.0312(11) 0.0594(14) 0.0006(10) 0.0036(11) 0.0016(11) C
C3 0.0621(17) 0.0526(15) 0.0642(17) -0.0013(13) -0.0138(14) 0.0053(13) C
C4 0.093(2) 0.0757(19) 0.0567(17) -0.0011(18) -0.0033(16) -0.0121(15) C
C5 0.0591(17) 0.0689(18) 0.0589(17) 0.0228(15) 0.056(14) 0.0182(15) C
C6 0.076(2) 0.106(3) 0.0682(19) 0.031(2) 0.0141(18) 0.0244(18) C
C7 0.078(3) 0.134(4) 0.094(3) 0.50(3) 0.059(4) 0.0057(3) C
C8 0.057(2) 0.088(2) 0.142(3) 0.0187(18) 0.031(2) 0.058(3) C
C9 0.0511(17) 0.0590(17) 0.104(2) 0.0084(14) 0.0119(16) 0.0284(16) C
C10 0.0449(15) 0.0440(13) 0.0682(17) 0.0117(12) 0.051(13) 0.0194(13) C
C11 0.0589(16) 0.0342(12) 0.0528(14) -0.0029(11) -0.0064(12) 0.0004(11) C
C12 0.0635(16) 0.0334(12) 0.0538(14) -0.0041(11) -0.0052(12) 0.0010(11) C
C13 0.0623(17) 0.0325(12) 0.0731(18) -0.0006(12) -0.0053(14) 0.0025(12) C
C14 0.0686(18) 0.0312(13) 0.0654(17) 0.0052(12) -0.0073(14) 0.0079(12) C
C15 0.0777(19) 0.0359(13) 0.0555(15) 0.0068(13) -0.0022(14) 0.0106(12) C
C16 0.078(2) 0.0557(16) 0.0627(17) 0.0003(15) -0.0004(16) 0.0129(14) C
C17 0.081(2) 0.091(2) 0.0682(19) 0.0061(19) 0.0178(18) 0.0247(19) C
C18 0.118(3) 0.086(3) 0.071(2) 0.027(2) 0.020(2) 0.025(2) C
C19 0.149(3) 0.0605(19) 0.0539(18) 0.024(2) 0.017(2) 0.0094(15) C
C20 0.110(2) 0.0415(15) 0.0536(16) 0.0103(16) -0.0048(16) 0.0099(13) C
C21 0.142(3) 0.0500(17) 0.0587(18) -0.0122(19) -0.0140(19) -0.0028(14) C
C22 0.094(2) 0.0496(16) 0.076(2) -0.0110(16) -0.0287(17) 0.0151(15) C
C23 0.0622(16) 0.0377(13) 0.0646(16) -0.0005(12) 0.0000(13) -0.0020(12) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
S 0.68174(8) 0.33120(6) 0.18805(6) 0.0812(5) Uij S
O1 0.49635(19) 1.05963(12) 0.22812(14) 0.0776(13) Uij O
O2 0.31184(18) 0.92564(13) 0.24066(14) 0.0817(14) Uij O
N1 0.44190(18) 0.46001(13) 0.31941(13) 0.0506(12) Uij N
N2 0.5322(2) 0.44679(13) 0.26566(13) 0.0549(12) Uij N
N3 0.4768(2) 0.27807(15) 0.25633(16) 0.0722(16) Uij N
C1 0.4326(2) 0.54882(16) 0.35344(15) 0.0460(13) Uij C
C2 0.5091(2) 0.64341(16) 0.34007(15) 0.0463(13) Uij C
C3 0.5653(3) 0.68571(19) 0.42932(17) 0.0624(15) Uij C
C4 0.4616(3) 0.7136(2) 0.48066(17) 0.0769(19) Uij C
C5 0.3603(3) 0.6322(2) 0.47997(17) 0.0628(16) Uij C
C6 0.2832(3) 0.6326(3) 0.54366(19) 0.083(2) Uij C
C7 0.1873(4) 0.5620(4) 0.5428(3) 0.100(3) Uij C
C8 0.1637(3) 0.4898(3) 0.4771(3) 0.094(3) Uij C
C9 0.2405(3) 0.4870(2) 0.4133(2) 0.0715(18) Uij C
C10 0.3421(2) 0.55685(18) 0.41560(17) 0.0529(14) Uij C
C11 0.4236(2) 0.71836(16) 0.28104(15) 0.0504(13) Uij C
C12 0.4956(2) 0.81525(16) 0.26348(15) 0.0519(14) Uij C
C13 0.4162(3) 0.89097(17) 0.20093(17) 0.0578(15) Uij C
C14 0.5048(3) 0.97997(18) 0.18899(17) 0.0572(15) Uij C
C15 0.6003(3) 0.96463(18) 0.13057(16) 0.0579(15) Uij C
C16 0.7045(3) 1.0320(2) 0.13529(18) 0.0669(17) Uij C
C17 0.7960(3) 1.0178(3) 0.0830(2) 0.081(2) Uij C
C18 0.7825(4) 0.9388(3) 0.0247(2) 0.091(2) Uij C
C19 0.6797(4) 0.8735(2) 0.01779(19) 0.088(2) Uij C
C20 0.5868(3) 0.88345(19) 0.07161(18) 0.0705(18) Uij C
C21 0.4756(4) 0.8092(2) 0.06671(18) 0.087(2) Uij C
C22 0.3674(3) 0.8466(2) 0.11149(19) 0.0780(18) Uij C
C23 0.5560(3) 0.35098(17) 0.23899(16) 0.0560(14) Uij C
HO2 0.267 0.966 0.205 0.0910 Uiso H
HN2 0.579 0.507 0.246 0.0647 Uiso H
HN3A 0.504 0.211 0.234 0.0830 Uiso H
HN3B 0.401 0.288 0.287 0.0830 Uiso H
H2 0.583 0.623 0.310 0.0557 Uiso H
H3A 0.617 0.748 0.422 0.0697 Uiso H
H3B 0.623 0.633 0.462 0.0697 Uiso H
H4A 0.503 0.726 0.542 0.0851 Uiso H
H4B 0.419 0.778 0.456 0.0851 Uiso H
H6 0.298 0.685 0.591 0.0934 Uiso H
H7 0.133 0.562 0.590 0.1121 Uiso H
H8 0.091 0.440 0.475 0.1057 Uiso H
H9 0.224 0.435 0.366 0.0814 Uiso H
H11A 0.348 0.738 0.309 0.0586 Uiso H
H11B 0.392 0.684 0.224 0.0586 Uiso H
H12A 0.524 0.851 0.320 0.0602 Uiso H
H12B 0.574 0.795 0.238 0.0602 Uiso H
H16 0.713 1.091 0.177 0.0755 Uiso H
H17 0.872 1.065 0.087 0.0901 Uiso H
H18 0.849 0.929 -0.014 0.1017 Uiso H
H19 0.671 0.818 -0.027 0.0979 Uiso H
H21A 0.440 0.797 0.004 0.0936 Uiso H
H21B 0.509 0.743 0.094 0.0936 Uiso H
H22A 0.318 0.901 0.075 0.0832 Uiso H
H22B 0.308 0.788 0.118 0.0832 Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
S 0.110 0.124 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3,-4,4 3,-1,5 -4,6,1
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . . 118.15(18) yes
N1 N2 C23 . . . 118.92(19) yes
N1 C1 C2 . . . 127.1(2) yes
N1 C1 C10 . . . 116.0(2) yes
C2 C1 C10 . . . 116.8(2) yes
C1 C2 C3 . . . 107.76(19) yes
C1 C2 C11 . . . 109.57(18) yes
C3 C2 C11 . . . 114.74(18) yes
C2 C3 C4 . . . 111.8(2) yes
C3 C4 C5 . . . 113.5(2) yes
C4 C5 C6 . . . 119.3(3) yes
C4 C5 C10 . . . 121.1(2) yes
C6 C5 C10 . . . 119.6(3) yes
C5 C6 C7 . . . 120.7(3) yes
C6 C7 C8 . . . 120.5(3) yes
C7 C8 C9 . . . 119.9(3) yes
C8 C9 C10 . . . 119.8(3) yes
C1 C10 C5 . . . 119.9(2) yes
C1 C10 C9 . . . 120.7(2) yes
C5 C10 C9 . . . 119.4(3) yes
C2 C11 C12 . . . 112.40(19) yes
C11 C12 C13 . . . 114.60(19) yes
O2 C13 C12 . . . 107.8(2) yes
O2 C13 C14 . . . 110.03(19) yes
O2 C13 C22 . . . 110.8(2) yes
C12 C13 C14 . . . 106.9(2) yes
C12 C13 C22 . . . 113.8(2) yes
C14 C13 C22 . . . 107.4(2) yes
O1 C14 C13 . . . 119.7(3) yes
O1 C14 C15 . . . 122.7(2) yes
C13 C14 C15 . . . 117.7(2) yes
C14 C15 C16 . . . 119.2(2) yes
C14 C15 C20 . . . 120.4(3) yes
C16 C15 C20 . . . 120.4(3) yes
C15 C16 C17 . . . 120.2(3) yes
C16 C17 C18 . . . 119.5(3) yes
C17 C18 C19 . . . 121.1(3) yes
C18 C19 C20 . . . 121.1(3) yes
C15 C20 C19 . . . 117.6(3) yes
C15 C20 C21 . . . 121.0(3) yes
C19 C20 C21 . . . 121.4(3) yes
C20 C21 C22 . . . 113.8(2) yes
C13 C22 C21 . . . 112.5(2) yes
S C23 N2 . . . 119.31(18) yes
S C23 N3 . . . 124.06(19) yes
N2 C23 N3 . . . 116.6(2) yes
O1 HN3A N3 . 1_565 1_565 151.3 ?
O1 HN3A N3 1_545 . . 151.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C23 1.669(3) yes
O1 C14 1.216(3) yes
O2 C13 1.418(3) yes
N1 N2 1.376(3) yes
N1 C1 1.285(3) yes
N2 C23 1.354(3) yes
N3 C23 1.320(3) yes
C1 C2 1.505(3) yes
C1 C10 1.469(3) yes
C2 C3 1.522(3) yes
C2 C11 1.528(3) yes
C3 C4 1.498(4) yes
C4 C5 1.502(4) yes
C5 C6 1.381(4) yes
C5 C10 1.395(4) yes
C6 C7 1.363(6) yes
C7 C8 1.384(7) yes
C8 C9 1.380(5) yes
C9 C10 1.399(4) yes
C11 C12 1.521(3) yes
C12 C13 1.534(3) yes
C13 C14 1.519(3) yes
C13 C22 1.519(4) yes
C14 C15 1.475(4) yes
C15 C16 1.396(4) yes
C15 C20 1.394(4) yes
C16 C17 1.371(5) yes
C17 C18 1.366(6) yes
C18 C19 1.364(6) yes
C19 C20 1.394(5) yes
C20 C21 1.509(5) yes
C21 C22 1.509(5) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 HN3A 1.98 1_565
O1 N3 2.90 1_565
N3 O1 2.90 1_545
HN3A O1 1.98 1_545
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
S C23 N2 N1 -169.7(2)
O1 C14 C13 O2 15.30(10)
O1 C14 C13 C12 -101.4(2)
O1 C14 C13 C22 136.1(3)
O1 C14 C15 C16 15.90(10)
O1 C14 C15 C20 -164.4(3)
O2 C13 C22 C21 179.7(3)
N1 C1 C2 C3 -128.8(2)
N1 C1 C2 C11 105.7(2)
N2 N1 C1 C2 1.20(10)
N2 N1 C1 C10 -175.4(2)
N3 C23 N2 N1 9.70(10)
C1 N1 N2 C23 170.9(3)
C1 C10 C5 C4 7.40(10)
C1 C10 C5 C6 -173.3(3)
C1 C10 C9 C8 174.0(3)
C2 C11 C12 C13 177.2(3)
C3 C4 C5 C6 160.5(3)
C3 C4 C5 C10 -20.20(10)
C4 C3 C2 C1 -60.2(2)
C4 C3 C2 C11 62.1(2)
C4 C5 C6 C7 177.5(4)
C5 C4 C3 C2 47.3(2)
C5 C6 C7 C8 -1.3(2)
C5 C10 C1 N1 154.5(3)
C5 C10 C1 C2 -22.40(10)
C5 C10 C9 C8 -3.4(2)
C9 C8 C7 C6 2.1(2)
C9 C10 C1 N1 -22.90(10)
C9 C10 C1 C2 160.2(3)
C9 C10 C5 C4 -175.2(3)
C9 C10 C5 C6 4.1(2)
C10 C1 C2 C3 47.7(2)
C10 C1 C2 C11 -77.8(2)
C10 C5 C6 C7 -1.8(2)
C10 C9 C8 C7 0.2(2)
C11 C12 C13 O2 63.8(2)
C11 C12 C13 C14 -178.0(3)
C11 C12 C13 C22 -59.6(2)
C12 C11 C2 C1 -179.0(3)
C12 C11 C2 C3 59.6(2)
C12 C13 C22 C21 -58.6(2)
C13 C14 C15 C16 -163.0(3)
C13 C14 C15 C20 16.70(10)
C14 C13 C22 C21 59.5(2)
C14 C15 C16 C17 178.5(3)
C14 C15 C20 C19 179.6(3)
C14 C15 C20 C21 -0.60(10)
C15 C14 C13 O2 -165.7(3)
C15 C14 C13 C12 77.5(2)
C15 C14 C13 C22 -45.0(2)
C15 C16 C17 C18 1.7(2)
C15 C20 C19 C18 2.2(2)
C15 C20 C21 C22 15.4(2)
C16 C15 C20 C19 -0.7(2)
C16 C15 C20 C21 179.1(3)
C16 C17 C18 C19 -0.2(2)
C19 C20 C21 C22 -164.7(4)
C20 C15 C16 C17 -1.2(2)
C20 C19 C18 C17 -1.8(2)
C20 C21 C22 C13 -46.1(2)
C21 C20 C19 C18 -177.7(4)