#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/04/7200468.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_7200468
loop_
_publ_author_name
'Kalita, Dipjyoti'
'Sarma, Rupam'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Formation of symmetry non-equivalent molecules in urea and carbamate
 derivatives: the role of anion
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              803
_journal_paper_doi               10.1039/b815962a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8403(8)
_cell_length_b                   10.5515(11)
_cell_length_c                   13.0173(11)
_cell_measurement_temperature    296(2)
_cell_volume                     1351.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0529
_diffrn_reflns_av_sigmaI/netI    0.1327
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8335
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0657
_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)+(0.0000P)²+0.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                1890
_reflns_number_total             3326
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815962a.txt
_cod_data_source_block           8hqphnco_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               7200468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9082(3) 0.4073(2) 0.3893(2) 0.0475(6) Uani 1 1 d . . .
C2 C 1.0057(4) 0.4577(4) 0.3253(2) 0.0774(11) Uani 1 1 d . . .
H2 H 1.0963 0.4340 0.3326 0.093 Uiso 1 1 calc R . .
C3 C 0.9684(4) 0.5437(5) 0.2500(3) 0.0951(14) Uani 1 1 d . . .
H3 H 1.0344 0.5765 0.2063 0.114 Uiso 1 1 calc R . .
C4 C 0.8354(4) 0.5813(3) 0.2388(2) 0.0745(10) Uani 1 1 d . . .
H4 H 0.8112 0.6395 0.1884 0.089 Uiso 1 1 calc R . .
C5 C 0.7401(4) 0.5318(3) 0.3030(2) 0.0631(8) Uani 1 1 d . . .
H5 H 0.6498 0.5565 0.2959 0.076 Uiso 1 1 calc R . .
C6 C 0.7748(3) 0.4449(3) 0.3790(2) 0.0555(7) Uani 1 1 d . . .
H6 H 0.7085 0.4124 0.4226 0.067 Uiso 1 1 calc R . .
C7 C 0.8765(3) 0.2438(2) 0.52409(18) 0.0466(6) Uani 1 1 d . . .
C8 C 0.8821(4) 0.1039(3) 0.7545(2) 0.0697(9) Uani 1 1 d . . .
H8 H 0.8922 0.1833 0.7846 0.084 Uiso 1 1 calc R . .
C9 C 0.9060(3) 0.0889(3) 0.6527(2) 0.0516(7) Uani 1 1 d . . .
C10 C 0.8946(3) -0.0294(3) 0.6051(2) 0.0578(7) Uani 1 1 d . . .
C11 C 0.9184(6) -0.1511(5) 0.4623(3) 0.125(2) Uani 1 1 d . . .
H11 H 0.9435 -0.1603 0.3938 0.150 Uiso 1 1 calc R . .
C12 C 0.8733(7) -0.2579(5) 0.5134(5) 0.152(3) Uani 1 1 d . . .
H12 H 0.8658 -0.3345 0.4785 0.182 Uiso 1 1 calc R . .
C13 C 0.8399(6) -0.2513(4) 0.6141(5) 0.1240(18) Uani 1 1 d . . .
H13 H 0.8107 -0.3233 0.6489 0.149 Uiso 1 1 calc R . .
C14 C 0.8500(4) -0.1335(3) 0.6662(3) 0.0758(10) Uani 1 1 d . . .
C15 C 0.8267(4) -0.1138(4) 0.7710(3) 0.0904(13) Uani 1 1 d . . .
H15 H 0.7996 -0.1818 0.8116 0.108 Uiso 1 1 calc R . .
C16 C 0.8423(4) -0.0001(5) 0.8144(3) 0.0871(13) Uani 1 1 d . . .
H16 H 0.8267 0.0101 0.8843 0.105 Uiso 1 1 calc R . .
N1 N 0.9287(3) -0.0379(3) 0.50288(19) 0.0811(9) Uani 1 1 d . . .
N3 N 0.9534(2) 0.3207(2) 0.46558(16) 0.0533(6) Uani 1 1 d . . .
H3A H 1.0398 0.3171 0.4755 0.064 Uiso 1 1 calc R . .
O1 O 0.7563(2) 0.22554(18) 0.51899(13) 0.0555(5) Uani 1 1 d . . .
O2 O 0.9584(2) 0.1909(2) 0.59753(15) 0.0625(6) Uani 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.6(3) . . ?
C6 C1 N3 123.5(2) . . ?
C2 C1 N3 116.9(3) . . ?
C1 C2 C3 119.7(3) . . ?
C4 C3 C2 121.1(3) . . ?
C5 C4 C3 118.7(3) . . ?
C4 C5 C6 121.4(3) . . ?
C1 C6 C5 119.5(3) . . ?
O1 C7 N3 128.3(2) . . ?
O1 C7 O2 123.6(2) . . ?
N3 C7 O2 108.1(2) . . ?
C9 C8 C16 120.0(3) . . ?
C8 C9 O2 118.5(3) . . ?
C8 C9 C10 121.6(3) . . ?
O2 C9 C10 119.4(2) . . ?
N1 C10 C9 117.8(3) . . ?
N1 C10 C14 124.4(3) . . ?
C9 C10 C14 117.8(3) . . ?
N1 C11 C12 125.0(5) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 119.3(4) . . ?
C15 C14 C13 125.7(4) . . ?
C15 C14 C10 118.7(3) . . ?
C13 C14 C10 115.5(4) . . ?
C16 C15 C14 121.8(3) . . ?
C15 C16 C8 120.1(3) . . ?
C11 N1 C10 115.5(4) . . ?
C7 N3 C1 127.4(2) . . ?
C7 O2 C9 117.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.378(4) . ?
C1 C2 1.378(4) . ?
C1 N3 1.421(3) . ?
C2 C3 1.385(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.361(4) . ?
C5 C6 1.392(4) . ?
C7 O1 1.201(3) . ?
C7 N3 1.346(3) . ?
C7 O2 1.369(3) . ?
C8 C9 1.355(4) . ?
C8 C16 1.403(5) . ?
C9 O2 1.393(3) . ?
C9 C10 1.398(4) . ?
C10 N1 1.375(4) . ?
C10 C14 1.425(4) . ?
C11 N1 1.311(5) . ?
C11 C12 1.382(8) . ?
C12 C13 1.354(7) . ?
C13 C14 1.420(5) . ?
C14 C15 1.400(5) . ?
C15 C16 1.334(5) . ?
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
C6 H6 O1 0.93 2.38 2.951(3) 119.1 .
N3 H3A O1 0.86 2.18 3.027(3) 168.6 4_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.2(6) . . . . ?
N3 C1 C2 C3 -179.3(4) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
N3 C1 C6 C5 179.0(2) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C16 C8 C9 O2 -173.7(3) . . . . ?
C16 C8 C9 C10 -1.3(5) . . . . ?
C8 C9 C10 N1 -176.1(3) . . . . ?
O2 C9 C10 N1 -3.8(4) . . . . ?
C8 C9 C10 C14 3.2(5) . . . . ?
O2 C9 C10 C14 175.5(3) . . . . ?
N1 C11 C12 C13 -2.3(10) . . . . ?
C11 C12 C13 C14 0.9(10) . . . . ?
C12 C13 C14 C15 -176.1(5) . . . . ?
C12 C13 C14 C10 0.6(7) . . . . ?
N1 C10 C14 C15 176.0(3) . . . . ?
C9 C10 C14 C15 -3.2(5) . . . . ?
N1 C10 C14 C13 -0.9(5) . . . . ?
C9 C10 C14 C13 179.9(4) . . . . ?
C13 C14 C15 C16 178.0(4) . . . . ?
C10 C14 C15 C16 1.5(6) . . . . ?
C14 C15 C16 C8 0.5(7) . . . . ?
C9 C8 C16 C15 -0.6(6) . . . . ?
C12 C11 N1 C10 1.9(8) . . . . ?
C9 C10 N1 C11 179.0(4) . . . . ?
C14 C10 N1 C11 -0.3(5) . . . . ?
O1 C7 N3 C1 6.0(4) . . . . ?
O2 C7 N3 C1 -171.0(2) . . . . ?
C6 C1 N3 C7 14.5(4) . . . . ?
C2 C1 N3 C7 -167.5(3) . . . . ?
O1 C7 O2 C9 15.8(4) . . . . ?
N3 C7 O2 C9 -167.1(2) . . . . ?
C8 C9 O2 C7 -113.8(3) . . . . ?
C10 C9 O2 C7 73.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 208971
