#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:34:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179586 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/51/4505157.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_4505157
loop_
_publ_author_name
'Custelcean, Radu'
'Ward, Michael D.'
_publ_section_title
;
 Chiral Discrimination in Low-Density Hydrogen-Bonded Frameworks
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2277
_journal_paper_doi               10.1021/cg050118x
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C10 H15 N4 O3 S'
_chemical_formula_weight         271.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.983(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4632(15)
_cell_length_b                   12.587(3)
_cell_length_c                   29.788(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2791.5(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9698
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+8.8117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1510
_reflns_number_gt                2851
_reflns_number_total             3034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050118xsi20050330_041228.cif
_cod_data_source_block
c:\mydocu~1\chem\postdoc\xray\ch3-ch~1\chiral~1\c2onc
_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:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' 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        2791.4(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4505157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.13050(8) 0.04579(5) 0.427300(19) 0.02708(18) Uani 1 1 d .
O1 O 0.2993(2) 0.10249(15) 0.43670(6) 0.0316(4) Uani 1 1 d .
O2 O 0.1393(2) -0.06481(15) 0.44211(6) 0.0329(4) Uani 1 1 d .
O3 O -0.0226(2) 0.10169(15) 0.44416(6) 0.0337(4) Uani 1 1 d .
C4 C 0.0903(3) 0.0420(2) 0.36796(8) 0.0283(5) Uani 1 1 d .
N2 N -0.3599(3) -0.01092(18) 0.45405(8) 0.0346(5) Uani 1 1 d .
H2A H -0.2604 0.0235 0.4539 0.042 Uiso 1 1 calc R
H2B H -0.4600 0.0230 0.4540 0.042 Uiso 1 1 calc R
N3 N -0.2052(3) -0.16873(18) 0.45437(8) 0.0330(5) Uani 1 1 d .
H3A H -0.1054 -0.1347 0.4542 0.040 Uiso 1 1 calc R
H3B H -0.2054 -0.2371 0.4545 0.040 Uiso 1 1 calc R
N1 N -0.5127(3) -0.16877(19) 0.45449(9) 0.0389(5) Uani 1 1 d .
H1A H -0.6126 -0.1347 0.4544 0.047 Uiso 1 1 calc R
H1B H -0.5124 -0.2371 0.4547 0.047 Uiso 1 1 calc R
C6 C -0.0983(4) -0.0171(2) 0.30341(9) 0.0368(6) Uani 1 1 d .
C8 C -0.3590(3) -0.1159(2) 0.45433(8) 0.0295(5) Uani 1 1 d .
C1 C 0.0177(4) 0.0341(2) 0.27533(8) 0.0355(6) Uani 1 1 d .
C5 C -0.0592(4) -0.0121(2) 0.34973(9) 0.0346(6) Uani 1 1 d .
H5 H -0.1348 -0.0457 0.3688 0.042 Uiso 1 1 calc R
C3 C 0.2062(4) 0.0916(3) 0.34044(10) 0.0459(7) Uani 1 1 d .
H3 H 0.3072 0.1273 0.3526 0.055 Uiso 1 1 calc R
C7 C -0.2633(5) -0.0774(4) 0.28531(11) 0.0611(10) Uani 1 1 d .
H7A H -0.2994 -0.1261 0.3077 0.092 Uiso 1 1 calc R
H7B H -0.2360 -0.1160 0.2588 0.092 Uiso 1 1 calc R
H7C H -0.3590 -0.0282 0.2778 0.092 Uiso 1 1 calc R
C2 C 0.1682(5) 0.0868(3) 0.29414(10) 0.0501(8) Uani 1 1 d .
H2 H 0.2455 0.1197 0.2753 0.060 Uiso 1 1 calc R
N2S N 0.3070(19) 0.2377(8) 0.1332(4) 0.299(9) Uani 1 1 d .
C3S C 0.282(4) 0.2556(15) 0.1725(5) 0.335(16) Uani 1 1 d .
C4S C 0.4171(11) 0.2157(7) 0.2028(4) 0.184(6) Uani 1 1 d .
H4S1 H 0.4734 0.1558 0.1897 0.276 Uiso 1 1 calc R
H4S2 H 0.3655 0.1941 0.2300 0.276 Uiso 1 1 calc R
H4S3 H 0.5052 0.2700 0.2096 0.276 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
_geom_angle_site_symmetry_3
O1 S1 O3 112.61(11) .
O1 S1 O2 112.86(11) .
O3 S1 O2 112.03(11) .
O1 S1 C4 106.77(11) .
O3 S1 C4 105.89(11) .
O2 S1 C4 106.05(12) .
C3 C4 C5 120.6(2) .
C3 C4 S1 120.7(2) .
C5 C4 S1 118.7(2) .
C5 C6 C1 118.4(3) .
C5 C6 C7 119.0(3) .
C1 C6 C7 122.6(3) .
N2 C8 N3 120.4(2) .
N2 C8 N1 119.8(2) .
N3 C8 N1 119.8(2) .
C2 C1 C6 119.6(2) .
C2 C1 C1 118.8(3) 2
C6 C1 C1 121.5(3) 2
C4 C5 C6 121.2(3) .
C4 C3 C2 118.5(3) .
C1 C2 C3 121.6(3) .
N2S C3S C4S 114(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4580(18) .
S1 O3 1.4601(19) .
S1 O2 1.4604(19) .
S1 C4 1.773(2) .
C4 C3 1.381(4) .
C4 C5 1.385(4) .
N2 C8 1.322(3) .
N3 C8 1.326(3) .
N1 C8 1.326(3) .
C6 C5 1.392(4) .
C6 C1 1.402(4) .
C6 C7 1.513(4) .
C1 C2 1.389(4) .
C1 C1 1.514(5) 2
C3 C2 1.390(4) .
N2S C3S 1.219(18) .
C3S C4S 1.40(3) .
