#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/43/4114395.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_4114395
loop_
_publ_author_name
'Venu R. Vangala'
'Balakrishna R. Bhogala'
'Archan Dey'
'Gautam R. Desiraju'
'Charlotte K. Broder'
'Philip S. Smith'
'Raju Mondal'
'Judith A. K. Howard'
'Chick C. Wilson'
_publ_contact_author_address
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_email       desiraju@uohyd.ernet.in
_publ_contact_author_fax         '91 40 3010567'
_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_phone       '91 40 3010567'
_publ_section_title
;
 Correspondence between Molecular Functionality and Crystal Structures.
 Supramolecular Chemistry of a Family of Homologated Aminophenols
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14495
_journal_page_last               14509
_journal_paper_doi               10.1021/ja037227p
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C12 H11 N O S2'
_chemical_formula_weight         249.34
_chemical_melting_point          387(1)
_chemical_name_systematic
; 
 4-(4-aminophenyldisulfamyl)phenol 
;
_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                 109.633(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4321(12)
_cell_length_b                   8.1179(11)
_cell_length_c                   14.791(2)
_cell_measurement_reflns_used    866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.568
_cell_measurement_theta_min      3.844
_cell_volume                     1179.8(3)
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL-98 (Bruker, 1998)'
_computing_publication_material  'SHELXTL-98 (Bruker, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART-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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8343
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.90251
_exptl_absorpt_correction_T_min  0.76269
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       'not refined'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.5577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2568
_reflns_number_total             2926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037227psi20030927_031934_11.cif
_cod_data_source_block           2c
_cod_database_code               4114395
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
O1 O 0.06813(12) -0.59361(14) -0.18514(8) 0.0269(3) Uani 1 1 d .
H1 H 0.006(2) -0.551(3) -0.2322(16) 0.036(6) Uiso 1 1 d .
C1 C 0.10043(15) -0.49276(18) -0.10682(11) 0.0214(3) Uani 1 1 d .
C2 C 0.22128(16) -0.52395(19) -0.03042(12) 0.0251(3) Uani 1 1 d .
H2 H 0.2792 -0.6114 -0.0351 0.030 Uiso 1 1 calc R
C3 C 0.25662(15) -0.4276(2) 0.05201(11) 0.0246(3) Uani 1 1 d .
H3 H 0.3383 -0.4499 0.1034 0.030 Uiso 1 1 calc R
C4 C 0.17242(15) -0.29776(19) 0.05964(11) 0.0219(3) Uani 1 1 d .
C5 C 0.05074(15) -0.26854(19) -0.01621(11) 0.0214(3) Uani 1 1 d .
H5 H -0.0080 -0.1824 -0.0109 0.026 Uiso 1 1 calc R
C6 C 0.01493(14) -0.36405(18) -0.09908(11) 0.0210(3) Uani 1 1 d .
H6 H -0.0672 -0.3422 -0.1503 0.025 Uiso 1 1 calc R
S1 S 0.21554(4) -0.17386(6) 0.16531(3) 0.02803(12) Uani 1 1 d .
S2 S 0.28422(4) 0.04105(5) 0.12423(3) 0.02696(11) Uani 1 1 d .
N1 N 0.87146(13) -0.04108(19) 0.15715(10) 0.0227(3) Uani 1 1 d .
H1A H 0.885(2) 0.008(3) 0.1130(17) 0.048(7) Uiso 1 1 d .
H1B H 0.894(2) -0.135(3) 0.1591(14) 0.028(5) Uiso 1 1 d .
C11 C 0.73180(15) -0.02641(19) 0.14852(10) 0.0205(3) Uani 1 1 d .
C12 C 0.65766(16) 0.11392(19) 0.10683(11) 0.0231(3) Uani 1 1 d .
H12 H 0.7000 0.1989 0.0829 0.028 Uiso 1 1 calc R
C13 C 0.52199(16) 0.12943(19) 0.10030(11) 0.0244(3) Uani 1 1 d .
H13 H 0.4716 0.2238 0.0704 0.029 Uiso 1 1 calc R
C14 C 0.45921(15) 0.00690(19) 0.13745(10) 0.0208(3) Uani 1 1 d .
C15 C 0.53368(15) -0.13205(19) 0.18080(11) 0.0230(3) Uani 1 1 d .
H15 H 0.4924 -0.2150 0.2071 0.028 Uiso 1 1 calc R
C16 C 0.66908(15) -0.14877(19) 0.18544(11) 0.0226(3) Uani 1 1 d .
H16A H 0.7190 -0.2443 0.2140 0.027 Uiso 1 1 calc R
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 H1 110.8(14)
O1 C1 C6 122.24(13)
O1 C1 C2 118.26(14)
C6 C1 C2 119.46(14)
C3 C2 C1 120.41(14)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 120.35(14)
C2 C3 H3 119.8
C4 C3 H3 119.8
C3 C4 C5 119.08(14)
C3 C4 S1 120.95(12)
C5 C4 S1 119.94(12)
C6 C5 C4 120.88(14)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 119.80(13)
C5 C6 H6 120.1
C1 C6 H6 120.1
C4 S1 S2 103.30(5)
C14 S2 S1 106.28(5)
C11 N1 H1A 109.7(17)
C11 N1 H1B 111.5(15)
H1A N1 H1B 112(2)
C16 C11 C12 119.28(14)
C16 C11 N1 120.31(14)
C12 C11 N1 120.34(14)
C13 C12 C11 120.21(14)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.48(14)
C12 C13 H13 119.8
C14 C13 H13 119.8
C15 C14 C13 119.48(14)
C15 C14 S2 124.34(12)
C13 C14 S2 116.17(12)
C14 C15 C16 119.86(14)
C14 C15 H15 120.1
C16 C15 H15 120.1
C15 C16 C11 120.66(14)
C15 C16 H16A 119.7
C11 C16 H16A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3651(19)
O1 H1 0.85(2)
C1 C6 1.403(2)
C1 C2 1.405(2)
C2 C3 1.390(2)
C2 H2 0.9500
C3 C4 1.401(2)
C3 H3 0.9500
C4 C5 1.403(2)
C4 S1 1.7845(16)
C5 C6 1.391(2)
C5 H5 0.9500
C6 H6 0.9500
S1 S2 2.0540(6)
S2 C14 1.7910(15)
N1 C11 1.4242(19)
N1 H1A 0.82(2)
N1 H1B 0.80(2)
C11 C16 1.398(2)
C11 C12 1.398(2)
C12 C13 1.392(2)
C12 H12 0.9500
C13 C14 1.401(2)
C13 H13 0.9500
C14 C15 1.397(2)
C15 C16 1.398(2)
C15 H15 0.9500
C16 H16A 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
O1 C1 C2 C3 -178.17(14)
C6 C1 C2 C3 -0.4(2)
C1 C2 C3 C4 -0.3(2)
C2 C3 C4 C5 1.3(2)
C2 C3 C4 S1 179.50(12)
C3 C4 C5 C6 -1.5(2)
S1 C4 C5 C6 -179.77(11)
C4 C5 C6 C1 0.8(2)
O1 C1 C6 C5 177.83(13)
C2 C1 C6 C5 0.2(2)
C3 C4 S1 S2 104.33(12)
C5 C4 S1 S2 -77.46(12)
C4 S1 S2 C14 -83.34(7)
C16 C11 C12 C13 -1.5(2)
N1 C11 C12 C13 -178.66(14)
C11 C12 C13 C14 1.6(2)
C12 C13 C14 C15 -0.4(2)
C12 C13 C14 S2 -179.81(12)
S1 S2 C14 C15 -8.33(14)
S1 S2 C14 C13 171.10(10)
C13 C14 C15 C16 -1.0(2)
S2 C14 C15 C16 178.45(12)
C14 C15 C16 C11 1.1(2)
C12 C11 C16 C15 0.1(2)
N1 C11 C16 C15 177.33(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660520
