#------------------------------------------------------------------------------
#$Date: 2012-02-25 23:28:46 +0000 (Sat, 25 Feb 2012) $
#$Revision: 35020 $
#$URL: svn://www.crystallography.net/cod/cif/1/1501663.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_1501663
loop_
_publ_author_name
'Hall, Matthew D.'
'Brimacombe, Kyle R.'
'Varonka, Matthew S.'
'Pluchino, Kristen M.'
'Monda, Julie K.'
'Li, Jiayang'
'Walsh, Martin J.'
'Boxer, Matthew B.'
'Warren, Timothy H.'
'Fales, Henry M.'
'Gottesman, Michael M.'
_publ_contact_author             'Michael M. Gottesman'
_publ_section_title
;
 Synthesis and structure-activity evaluation of
 isatin-\b-thiosemicarbazones with improved selective activity toward
 multidrug-resistant cells expressing P-glycoprotein.
;
_journal_issue                   16
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              5878
_journal_page_last               5889
_journal_volume                  54
_journal_year                    2011
_chemical_formula_moiety         'C16 H14 N4 O S'
_chemical_formula_sum            'C16 H14 N4 O S'
_chemical_formula_weight         310.37
_chemical_name_common            6
_chemical_name_systematic
; 
 ? 
;
_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                 100.7300(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7856(9)
_cell_length_b                   5.4114(3)
_cell_length_c                   16.1237(8)
_cell_measurement_reflns_used    4066
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.082
_cell_measurement_theta_min      2.47
_cell_volume                     1438.97(13)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker APEXII'
_computing_molecular_graphics
'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'APEXII platform CCD Bruker'
_diffrn_measurement_method       'omega 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11767
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0332
_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/[\s^2^(Fo^2^)+(0.0389P)^2^+0.6167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                2691
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    jm2006047_si_003.cif
_[local]_cod_data_source_block   cmpd6
_[local]_cod_cif_authors_sg_H-M  P21/c
_[local]_cod_cif_authors_sg_Hall -P2ybc
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

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_database_code               1501663
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 0.26276(2) 0.42698(7) 0.25682(2) 0.02002(11) Uani 1 1 d .
O1 O 0.08255(6) 1.0307(2) 0.26374(6) 0.0217(2) Uani 1 1 d .
N2 N 0.22339(7) 0.9540(2) 0.40799(7) 0.0158(3) Uani 1 1 d .
N4 N 0.32770(7) 0.5799(2) 0.41318(7) 0.0166(3) Uani 1 1 d .
H7 H 0.3292 0.6911 0.4532 0.020 Uiso 1 1 calc R
N3 N 0.21997(7) 0.8011(2) 0.34107(7) 0.0166(3) Uani 1 1 d .
H6 H 0.1829 0.8265 0.2956 0.020 Uiso 1 1 calc R
C7 C 0.17733(9) 1.5725(3) 0.58407(9) 0.0226(3) Uani 1 1 d .
H4 H 0.2060 1.6136 0.6388 0.027 Uiso 1 1 calc R
N1 N 0.05812(7) 1.3628(2) 0.34604(7) 0.0192(3) Uani 1 1 d .
H1 H 0.0155 1.4258 0.3127 0.023 Uiso 1 1 calc R
C16 C 0.47656(8) 0.6274(3) 0.34980(8) 0.0162(3) Uani 1 1 d .
H14 H 0.4366 0.7537 0.3399 0.019 Uiso 1 1 calc R
C2 C 0.16778(8) 1.1229(3) 0.40075(8) 0.0156(3) Uani 1 1 d .
C3 C 0.15911(8) 1.3137(3) 0.46206(9) 0.0162(3) Uani 1 1 d .
C12 C 0.52324(8) 0.2369(3) 0.40995(9) 0.0175(3) Uani 1 1 d .
H10 H 0.5150 0.0937 0.4414 0.021 Uiso 1 1 calc R
C11 C 0.46337(8) 0.4192(3) 0.39537(8) 0.0148(3) Uani 1 1 d .
C6 C 0.11142(9) 1.7156(3) 0.54704(10) 0.0224(3) Uani 1 1 d .
H3 H 0.0959 1.8533 0.5770 0.027 Uiso 1 1 calc R
C13 C 0.59453(8) 0.2623(3) 0.37906(9) 0.0183(3) Uani 1 1 d .
H11 H 0.6349 0.1373 0.3896 0.022 Uiso 1 1 calc R
C1 C 0.09892(8) 1.1620(3) 0.32722(9) 0.0176(3) Uani 1 1 d .
C14 C 0.60690(9) 0.4701(3) 0.33273(9) 0.0182(3) Uani 1 1 d .
H12 H 0.6554 0.4871 0.3109 0.022 Uiso 1 1 calc R
C9 C 0.27286(8) 0.6075(3) 0.34243(9) 0.0164(3) Uani 1 1 d .
C8 C 0.20185(9) 1.3704(3) 0.54204(9) 0.0199(3) Uani 1 1 d .
H5 H 0.2469 1.2730 0.5675 0.024 Uiso 1 1 calc R
C15 C 0.54825(8) 0.6526(3) 0.31841(9) 0.0175(3) Uani 1 1 d .
H13 H 0.5568 0.7957 0.2871 0.021 Uiso 1 1 calc R
C4 C 0.09243(8) 1.4590(3) 0.42593(9) 0.0172(3) Uani 1 1 d .
C10 C 0.38516(8) 0.3764(3) 0.42786(9) 0.0171(3) Uani 1 1 d .
H9 H 0.3586 0.2262 0.4006 0.021 Uiso 1 1 calc R
H8 H 0.3988 0.3442 0.4893 0.021 Uiso 1 1 calc R
C5 C 0.06757(9) 1.6611(3) 0.46690(10) 0.0204(3) Uani 1 1 d .
H2 H 0.0225 1.7588 0.4416 0.025 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0234(2) 0.0210(2) 0.01537(18) -0.00260(14) 0.00307(14) -0.00124(14)
O1 0.0174(5) 0.0270(6) 0.0188(5) -0.0026(4) -0.0016(4) -0.0024(4)
N2 0.0149(6) 0.0179(6) 0.0152(6) 0.0001(5) 0.0040(4) -0.0027(5)
N4 0.0149(6) 0.0196(6) 0.0151(6) -0.0020(5) 0.0022(4) 0.0008(5)
N3 0.0156(6) 0.0200(6) 0.0134(6) -0.0016(5) 0.0006(4) 0.0002(5)
C7 0.0215(7) 0.0287(8) 0.0176(7) -0.0033(6) 0.0038(6) -0.0027(6)
N1 0.0129(6) 0.0240(7) 0.0190(6) 0.0015(5) -0.0017(5) 0.0013(5)
C16 0.0161(7) 0.0163(7) 0.0154(6) -0.0010(5) 0.0005(5) -0.0002(5)
C2 0.0119(6) 0.0200(7) 0.0146(6) 0.0022(5) 0.0014(5) -0.0037(5)
C3 0.0136(6) 0.0182(7) 0.0175(7) 0.0017(5) 0.0045(5) -0.0022(5)
C12 0.0207(7) 0.0156(7) 0.0155(7) 0.0007(5) 0.0017(5) 0.0004(6)
C11 0.0154(7) 0.0167(7) 0.0115(6) -0.0024(5) 0.0007(5) -0.0013(5)
C6 0.0230(8) 0.0209(8) 0.0257(8) -0.0032(6) 0.0108(6) -0.0021(6)
C13 0.0175(7) 0.0186(7) 0.0179(7) -0.0027(6) 0.0008(5) 0.0029(5)
C1 0.0125(6) 0.0217(7) 0.0181(7) 0.0032(6) 0.0018(5) -0.0036(5)
C14 0.0151(7) 0.0234(8) 0.0161(7) -0.0041(6) 0.0027(5) -0.0029(6)
C9 0.0150(7) 0.0190(7) 0.0161(7) 0.0012(6) 0.0050(5) -0.0042(5)
C8 0.0162(7) 0.0251(8) 0.0180(7) 0.0006(6) 0.0023(5) 0.0008(6)
C15 0.0202(7) 0.0169(7) 0.0150(7) 0.0004(5) 0.0021(5) -0.0040(6)
C4 0.0135(7) 0.0201(7) 0.0181(7) 0.0031(6) 0.0032(5) -0.0038(5)
C10 0.0164(7) 0.0176(7) 0.0172(7) 0.0022(6) 0.0029(5) 0.0000(5)
C5 0.0160(7) 0.0198(7) 0.0266(8) 0.0038(6) 0.0069(6) 0.0009(6)
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
C2 N2 N3 115.90(11)
C9 N4 C10 123.74(12)
C9 N4 H7 118.1
C10 N4 H7 118.1
N2 N3 C9 121.58(11)
N2 N3 H6 119.2
C9 N3 H6 119.2
C8 C7 C6 120.89(14)
C8 C7 H4 119.6
C6 C7 H4 119.6
C1 N1 C4 111.40(12)
C1 N1 H1 124.3
C4 N1 H1 124.3
C11 C16 C15 120.36(13)
C11 C16 H14 119.8
C15 C16 H14 119.8
N2 C2 C3 126.91(12)
N2 C2 C1 127.08(13)
C3 C2 C1 106.01(12)
C8 C3 C4 119.77(13)
C8 C3 C2 133.47(13)
C4 C3 C2 106.77(12)
C13 C12 C11 120.78(13)
C13 C12 H10 119.6
C11 C12 H10 119.6
C16 C11 C12 118.87(13)
C16 C11 C10 122.73(12)
C12 C11 C10 118.37(12)
C7 C6 C5 121.38(14)
C7 C6 H3 119.3
C5 C6 H3 119.3
C12 C13 C14 119.99(13)
C12 C13 H11 120.0
C14 C13 H11 120.0
O1 C1 N1 127.33(13)
O1 C1 C2 126.22(13)
N1 C1 C2 106.42(12)
C15 C14 C13 119.70(13)
C15 C14 H12 120.2
C13 C14 H12 120.2
N4 C9 N3 116.17(12)
N4 C9 S1 125.97(11)
N3 C9 S1 117.85(10)
C3 C8 C7 118.57(14)
C3 C8 H5 120.7
C7 C8 H5 120.7
C14 C15 C16 120.30(13)
C14 C15 H13 119.8
C16 C15 H13 119.8
C5 C4 C3 122.26(13)
C5 C4 N1 128.38(13)
C3 C4 N1 109.36(12)
N4 C10 C11 114.72(12)
N4 C10 H9 108.6
C11 C10 H9 108.6
N4 C10 H8 108.6
C11 C10 H8 108.6
H9 C10 H8 107.6
C4 C5 C6 117.13(14)
C4 C5 H2 121.4
C6 C5 H2 121.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.6737(14)
O1 C1 1.2340(18)
N2 C2 1.2961(18)
N2 N3 1.3524(16)
N4 C9 1.3342(18)
N4 C10 1.4538(18)
N4 H7 0.8800
N3 C9 1.3708(18)
N3 H6 0.8800
C7 C8 1.389(2)
C7 C6 1.391(2)
C7 H4 0.9500
N1 C1 1.3491(19)
N1 C4 1.4092(18)
N1 H1 0.8800
C16 C11 1.385(2)
C16 C15 1.3963(19)
C16 H14 0.9500
C2 C3 1.455(2)
C2 C1 1.5086(18)
C3 C8 1.388(2)
C3 C4 1.403(2)
C12 C13 1.3860(19)
C12 C11 1.3967(19)
C12 H10 0.9500
C11 C10 1.5190(19)
C6 C5 1.394(2)
C6 H3 0.9500
C13 C14 1.387(2)
C13 H11 0.9500
C14 C15 1.383(2)
C14 H12 0.9500
C8 H5 0.9500
C15 H13 0.9500
C4 C5 1.382(2)
C10 H9 0.9900
C10 H8 0.9900
C5 H2 0.9500
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
C2 N2 N3 C9 -176.80(12)
N3 N2 C2 C3 -178.16(12)
N3 N2 C2 C1 1.9(2)
N2 C2 C3 C8 -1.8(3)
C1 C2 C3 C8 178.20(15)
N2 C2 C3 C4 177.88(13)
C1 C2 C3 C4 -2.13(14)
C15 C16 C11 C12 0.6(2)
C15 C16 C11 C10 -177.32(12)
C13 C12 C11 C16 -0.4(2)
C13 C12 C11 C10 177.64(13)
C8 C7 C6 C5 0.2(2)
C11 C12 C13 C14 -0.3(2)
C4 N1 C1 O1 177.18(14)
C4 N1 C1 C2 -1.05(15)
N2 C2 C1 O1 3.7(2)
C3 C2 C1 O1 -176.29(13)
N2 C2 C1 N1 -178.05(13)
C3 C2 C1 N1 1.96(14)
C12 C13 C14 C15 0.7(2)
C10 N4 C9 N3 176.02(12)
C10 N4 C9 S1 -3.4(2)
N2 N3 C9 N4 -0.21(19)
N2 N3 C9 S1 179.22(10)
C4 C3 C8 C7 -0.4(2)
C2 C3 C8 C7 179.19(15)
C6 C7 C8 C3 0.0(2)
C13 C14 C15 C16 -0.5(2)
C11 C16 C15 C14 -0.2(2)
C8 C3 C4 C5 0.7(2)
C2 C3 C4 C5 -179.01(13)
C8 C3 C4 N1 -178.71(12)
C2 C3 C4 N1 1.57(15)
C1 N1 C4 C5 -179.68(14)
C1 N1 C4 C3 -0.31(16)
C9 N4 C10 C11 86.87(16)
C16 C11 C10 N4 -4.62(19)
C12 C11 C10 N4 177.45(12)
C3 C4 C5 C6 -0.5(2)
N1 C4 C5 C6 178.81(14)
C7 C6 C5 C4 0.0(2)