#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:29:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180437 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/06/7210614.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_7210614
loop_
_publ_author_name
'Martins, Inês'
'Martins, Marta'
'Fernandes, Auguste'
'André, Vânia'
'Duarte, M. Teresa'
_publ_section_title
;
 An insight into dapsone co-crystals: sulfones as participants in
 supramolecular interactions
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              8173
_journal_paper_doi               10.1039/c3ce41323c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C12 H12 N2 O2 S, C6 H11 N O'
_chemical_formula_sum            'C18 H23 N3 O3 S'
_chemical_formula_weight         361.45
_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                 99.089(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2700(6)
_cell_length_b                   37.058(3)
_cell_length_c                   5.9595(4)
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.160
_cell_measurement_theta_min      2.49
_cell_volume                     1803.5(2)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 3.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0982
_diffrn_reflns_av_sigmaI/netI    0.1239
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            16909
_diffrn_reflns_theta_full        28.16
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0581
_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)+(0.0409P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                2360
_reflns_number_total             4375
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ce41323c.txt
_cod_data_source_block           dapcapro
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7210614
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
C1 C 0.2355(2) 0.13889(7) 0.5052(4) 0.0201(6) Uani 1 1 d .
C2 C 0.1994(3) 0.11236(8) 0.6534(4) 0.0243(6) Uani 1 1 d .
H2 H 0.1636 0.1189 0.7880 0.029 Uiso 1 1 calc R
C3 C 0.2160(3) 0.07654(8) 0.6040(4) 0.0266(6) Uani 1 1 d .
H3 H 0.1902 0.0590 0.7044 0.032 Uiso 1 1 calc R
C4 C 0.2716(3) 0.06610(8) 0.4028(4) 0.0252(6) Uani 1 1 d .
C5 C 0.3087(3) 0.09310(8) 0.2566(4) 0.0283(6) Uani 1 1 d .
H5 H 0.3467 0.0867 0.1232 0.034 Uiso 1 1 calc R
C6 C 0.2902(3) 0.12897(7) 0.3051(4) 0.0251(6) Uani 1 1 d .
H6 H 0.3143 0.1466 0.2043 0.030 Uiso 1 1 calc R
C7 C 0.0099(3) 0.19517(6) 0.4309(4) 0.0186(5) Uani 1 1 d .
C8 C -0.1256(3) 0.18670(7) 0.5336(4) 0.0211(6) Uani 1 1 d .
H8 H -0.1108 0.1757 0.6756 0.025 Uiso 1 1 calc R
C9 C -0.2803(3) 0.19452(7) 0.4262(4) 0.0261(6) Uani 1 1 d .
H9 H -0.3698 0.1891 0.4971 0.031 Uiso 1 1 calc R
C10 C -0.3055(3) 0.21055(7) 0.2116(4) 0.0249(6) Uani 1 1 d .
C11 C -0.1684(3) 0.21826(7) 0.1077(4) 0.0253(6) Uani 1 1 d .
H11 H -0.1830 0.2286 -0.0362 0.030 Uiso 1 1 calc R
C12 C -0.0125(3) 0.21061(7) 0.2167(4) 0.0235(6) Uani 1 1 d .
H12 H 0.0775 0.2158 0.1464 0.028 Uiso 1 1 calc R
C13 C 0.6972(3) 0.03426(7) 1.1084(4) 0.0245(6) Uani 1 1 d .
C14 C 0.8496(3) 0.05562(7) 1.1965(4) 0.0302(7) Uani 1 1 d .
H14A H 0.9284 0.0524 1.0937 0.036 Uiso 1 1 calc R
H14B H 0.8976 0.0460 1.3433 0.036 Uiso 1 1 calc R
C15 C 0.8193(3) 0.09569(7) 1.2215(4) 0.0317(7) Uani 1 1 d .
H15A H 0.9070 0.1055 1.3318 0.038 Uiso 1 1 calc R
H15B H 0.7180 0.0988 1.2820 0.038 Uiso 1 1 calc R
C16 C 0.8084(3) 0.11745(7) 1.0037(4) 0.0314(7) Uani 1 1 d .
H16A H 0.7979 0.1428 1.0402 0.038 Uiso 1 1 calc R
H16B H 0.9102 0.1146 0.9441 0.038 Uiso 1 1 calc R
C17 C 0.6678(3) 0.10733(8) 0.8186(4) 0.0312(7) Uani 1 1 d .
H17A H 0.5653 0.1122 0.8725 0.037 Uiso 1 1 calc R
H17B H 0.6720 0.1226 0.6872 0.037 Uiso 1 1 calc R
C18 C 0.6694(3) 0.06829(8) 0.7455(4) 0.0309(7) Uani 1 1 d .
H18A H 0.5991 0.0658 0.5999 0.037 Uiso 1 1 calc R
H18B H 0.7798 0.0620 0.7239 0.037 Uiso 1 1 calc R
N1 N 0.2830(3) 0.03018(7) 0.3496(5) 0.0359(6) Uani 1 1 d .
N2 N -0.4591(3) 0.21972(8) 0.1088(6) 0.0497(8) Uani 1 1 d .
N3 N 0.6158(3) 0.04266(6) 0.9049(3) 0.0253(5) Uani 1 1 d .
O1 O 0.20749(19) 0.18661(5) 0.8108(3) 0.0338(5) Uani 1 1 d .
O2 O 0.32211(18) 0.20540(5) 0.4670(3) 0.0346(5) Uani 1 1 d .
O3 O 0.6464(2) 0.01038(5) 1.2262(3) 0.0364(5) Uani 1 1 d .
S1 S 0.20640(7) 0.184385(19) 0.56912(11) 0.02496(19) Uani 1 1 d .
H1N1 H 0.286(3) 0.0123(8) 0.472(5) 0.047(9) Uiso 1 1 d .
H1N2 H -0.547(4) 0.2128(8) 0.168(5) 0.058(10) Uiso 1 1 d .
H1N3 H 0.532(3) 0.0281(8) 0.866(4) 0.044(9) Uiso 1 1 d .
H2N1 H 0.339(3) 0.0263(8) 0.255(5) 0.051(11) Uiso 1 1 d .
H2N2 H -0.473(3) 0.2286(8) -0.019(5) 0.040(10) 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
C2 C1 C6 119.4(2)
C2 C1 S1 119.55(19)
C6 C1 S1 121.00(19)
C3 C2 C1 120.7(2)
C2 C3 C4 120.5(2)
N1 C4 C5 121.4(2)
N1 C4 C3 120.5(2)
C5 C4 C3 118.1(3)
C6 C5 C4 121.4(2)
C5 C6 C1 119.9(2)
C12 C7 C8 119.8(2)
C12 C7 S1 120.56(17)
C8 C7 S1 119.57(18)
C9 C8 C7 120.3(2)
C8 C9 C10 120.8(2)
N2 C10 C9 120.7(2)
N2 C10 C11 120.7(2)
C9 C10 C11 118.5(2)
C12 C11 C10 120.7(2)
C11 C12 C7 119.9(2)
O3 C13 N3 121.0(2)
O3 C13 C14 121.0(2)
N3 C13 C14 118.0(2)
C13 C14 C15 113.9(2)
C14 C15 C16 115.1(2)
C17 C16 C15 115.2(2)
C18 C17 C16 113.9(2)
N3 C18 C17 114.7(2)
C13 N3 C18 125.8(2)
O1 S1 O2 119.43(11)
O1 S1 C7 108.45(10)
O2 S1 C7 107.89(11)
O1 S1 C1 107.02(11)
O2 S1 C1 107.75(11)
C7 S1 C1 105.47(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(3)
C1 C6 1.390(3)
C1 S1 1.754(3)
C2 C3 1.371(4)
C3 C4 1.405(3)
C4 N1 1.375(3)
C4 C5 1.392(3)
C5 C6 1.374(3)
C7 C12 1.384(3)
C7 C8 1.395(3)
C7 S1 1.748(2)
C8 C9 1.368(3)
C9 C10 1.396(3)
C10 N2 1.364(3)
C10 C11 1.404(3)
C11 C12 1.378(3)
C13 O3 1.243(3)
C13 N3 1.328(3)
C13 C14 1.510(3)
C14 C15 1.517(4)
C15 C16 1.519(3)
C16 C17 1.518(3)
C17 C18 1.511(4)
C18 N3 1.460(3)
O1 S1 1.4412(16)
O2 S1 1.4412(17)
