#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/78/7207804.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_7207804
loop_
_publ_author_name
'Graus, Sara'
'Uriel, Santiago'
'Serrano, José Luis'
_publ_section_title
;
 Supramolecular hydrogen-bonding patterns in 4′-substituted
 cyclohexane-5-spirohydantoin
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3759
_journal_paper_doi               10.1039/c2ce06560f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C16 H19 N2 O5.5'
_chemical_formula_weight         327.33
_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                 113.540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.003(4)
_cell_length_b                   13.847(3)
_cell_length_c                   12.636(2)
_cell_measurement_temperature    293(2)
_cell_volume                     3208.7(11)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.833
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ/ω 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2643
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.84
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0533
_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/[σ²(Fo²)+(0.0602P)²+4.9889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                1645
_reflns_number_total             2358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06560f.txt
_cod_data_source_block           strz71
_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_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C16 H19 N2 O5.50'
_cod_database_code               7207804
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
N1 N 0.20762(16) 0.04444(17) 0.6003(2) 0.0375(7) Uani 1 1 d .
HN1 H 0.204(2) 0.035(3) 0.664(3) 0.058(11) Uiso 1 1 d .
O1 O 0.25034(14) 0.20226(14) 0.63074(18) 0.0482(7) Uani 1 1 d .
C1 C 0.22910(18) 0.1291(2) 0.5706(2) 0.0370(8) Uani 1 1 d .
N2 N 0.22404(16) 0.11941(18) 0.4575(2) 0.0407(7) Uani 1 1 d .
HN2 H 0.237(2) 0.170(3) 0.427(3) 0.068(12) Uiso 1 1 d .
O2 O 0.19101(14) -0.00117(15) 0.31815(18) 0.0515(7) Uani 1 1 d .
C2 C 0.19969(18) 0.0295(2) 0.4135(2) 0.0364(8) Uani 1 1 d .
O3 O 0.09643(13) -0.25850(14) 0.49146(18) 0.0453(6) Uani 1 1 d .
C3 C 0.18275(17) -0.02530(19) 0.5047(2) 0.0310(7) Uani 1 1 d .
O4 O 0.07002(17) -0.72161(17) 0.4786(2) 0.0701(8) Uani 1 1 d .
C4 C 0.2238(2) -0.1222(2) 0.5385(3) 0.0351(8) Uani 1 1 d .
H4B H 0.2765(19) -0.111(2) 0.571(2) 0.033(9) Uiso 1 1 d .
H4A H 0.2106(17) -0.159(2) 0.466(3) 0.042(9) Uiso 1 1 d .
O5 O 0.10280(14) -0.68621(15) 0.6661(2) 0.0546(7) Uani 1 1 d .
C5 C 0.20468(19) -0.1763(2) 0.6285(3) 0.0369(8) Uani 1 1 d .
H5B H 0.2307(17) -0.240(2) 0.647(3) 0.046(9) Uiso 1 1 d .
H5A H 0.2235(15) -0.138(2) 0.702(2) 0.033(8) Uiso 1 1 d .
C6 C 0.1225(2) -0.1910(2) 0.5891(3) 0.0399(9) Uani 1 1 d .
H6 H 0.1104(18) -0.220(2) 0.652(3) 0.058(10) Uiso 1 1 d .
C7 C 0.0795(2) -0.0976(2) 0.5478(3) 0.0420(9) Uani 1 1 d .
H7B H 0.0878(15) -0.054(2) 0.613(3) 0.030(7) Uiso 1 1 d .
H7A H 0.025(2) -0.113(3) 0.514(3) 0.070(13) Uiso 1 1 d .
C8 C 0.09979(19) -0.0426(2) 0.4590(3) 0.0396(8) Uani 1 1 d .
H8B H 0.0702(18) 0.021(3) 0.436(3) 0.056(10) Uiso 1 1 d .
H8A H 0.0856(19) -0.075(2) 0.387(3) 0.057(10) Uiso 1 1 d .
C9 C 0.09984(18) -0.3563(2) 0.5145(3) 0.0383(8) Uani 1 1 d .
C10 C 0.07603(19) -0.4167(2) 0.4181(3) 0.0419(9) Uani 1 1 d .
H10 H 0.0602(19) -0.390(3) 0.342(3) 0.061(11) Uiso 1 1 d .
C11 C 0.07375(19) -0.5164(2) 0.4322(3) 0.0435(9) Uani 1 1 d .
H11 H 0.0566(18) -0.557(2) 0.360(3) 0.056(10) Uiso 1 1 d .
C12 C 0.09561(18) -0.5567(2) 0.5428(3) 0.0389(8) Uani 1 1 d .
C13 C 0.1206(2) -0.4957(2) 0.6374(3) 0.0485(9) Uani 1 1 d .
H13 H 0.137(2) -0.524(3) 0.716(3) 0.069(11) Uiso 1 1 d .
C14 C 0.1241(2) -0.3958(2) 0.6251(3) 0.0488(10) Uani 1 1 d .
H14 H 0.1460(19) -0.354(3) 0.699(3) 0.061(10) Uiso 1 1 d .
C15 C 0.08825(19) -0.6629(2) 0.5560(3) 0.0457(9) Uani 1 1 d .
C16 C 0.0952(2) -0.7863(2) 0.6923(3) 0.0629(11) Uani 1 1 d .
H16C H 0.1070 -0.7930 0.7734 0.094 Uiso 1 1 calc R
H16B H 0.1276 -0.8255 0.6713 0.094 Uiso 1 1 calc R
H16A H 0.0458 -0.8068 0.6494 0.094 Uiso 1 1 calc R
O10 O 0.5000 -0.6816(5) 0.7500 0.164(3) Uiso 1 2 d S
HO1 H 0.4738 -0.7032 0.6703 0.181 Uiso 0.50 1 d PR
HO2 H 0.4600 -0.6873 0.7356 0.181 Uiso 0.50 1 d PR
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C3 112.5(2)
O1 C1 N1 127.6(3)
O1 C1 N2 125.0(3)
N1 C1 N2 107.4(2)
C2 N2 C1 111.7(2)
O2 C2 N2 127.1(3)
O2 C2 C3 125.7(3)
N2 C2 C3 107.2(2)
C9 O3 C6 118.4(2)
N1 C3 C2 100.9(2)
N1 C3 C4 112.1(2)
C2 C3 C4 112.8(3)
N1 C3 C8 111.8(2)
C2 C3 C8 108.9(2)
C4 C3 C8 110.0(2)
C5 C4 C3 111.6(3)
C15 O5 C16 117.9(3)
C6 C5 C4 112.2(3)
O3 C6 C7 106.9(3)
O3 C6 C5 109.5(3)
C7 C6 C5 112.6(3)
C6 C7 C8 113.1(3)
C7 C8 C3 111.2(3)
O3 C9 C10 115.6(3)
O3 C9 C14 124.3(3)
C10 C9 C14 120.0(3)
C9 C10 C11 119.9(3)
C10 C11 C12 120.5(3)
C13 C12 C11 118.7(3)
C13 C12 C15 121.5(3)
C11 C12 C15 119.8(3)
C12 C13 C14 121.7(3)
C9 C14 C13 119.1(3)
O4 C15 O5 123.2(3)
O4 C15 C12 125.6(3)
O5 C15 C12 111.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.352(4)
N1 C3 1.469(4)
O1 C1 1.236(3)
C1 N2 1.398(4)
N2 C2 1.371(4)
O2 C2 1.223(3)
C2 C3 1.527(4)
O3 C9 1.381(4)
O3 C6 1.467(4)
C3 C4 1.542(4)
C3 C8 1.543(5)
O4 C15 1.210(4)
C4 C5 1.533(4)
O5 C15 1.341(4)
O5 C16 1.447(4)
C5 C6 1.529(5)
C6 C7 1.526(5)
C7 C8 1.538(5)
C9 C10 1.395(4)
C9 C14 1.395(4)
C10 C11 1.396(4)
C11 C12 1.402(4)
C12 C13 1.384(5)
C12 C15 1.495(4)
C13 C14 1.397(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O2 0.85(4) 2.12(4) 2.963(3) 175(4) 6_556
N2 HN2 O1 0.88(4) 1.98(4) 2.839(3) 167(4) 7_556
O10 HO1 O4 0.98 2.02 2.979(4) 166.4 7_536
