#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/28/7202821.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_7202821
loop_
_publ_author_name
'Wu, Biao'
'Huang, Xiaojuan'
'Xia, Yazhao'
'Yang, Xiao-Juan'
'Janiak, Christoph'
_publ_section_title
;
 Oxo-anion binding by protonated (dimethylphenyl)(pyridyl)ureas
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              676
_journal_paper_doi               10.1039/b702278f
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C14 H16 Cl N3 O5'
_chemical_formula_weight         341.75
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.659(2)
_cell_length_b                   12.283(3)
_cell_length_c                   21.669(4)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.79
_cell_measurement_theta_min      2.57
_cell_volume                     3103.2(11)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18593
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0567
_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)+(0.1120P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1922
_reflns_number_gt                1511
_reflns_number_total             3782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b702278f.txt
_cod_data_source_block           compound_6
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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      Pbca
_cod_database_code               7202821
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'
'-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
Cl Cl -0.29515(7) -0.05903(7) 0.56504(4) 0.0550(3) Uani 1 1 d . . .
O5 O -0.3100(3) -0.1513(3) 0.52956(19) 0.1400(16) Uani 1 1 d . . .
O2 O -0.3915(3) -0.0452(3) 0.60401(16) 0.1091(11) Uani 1 1 d . . .
O3 O -0.1938(2) -0.0735(2) 0.60166(14) 0.0856(9) Uani 1 1 d . . .
O4 O -0.2815(3) 0.0364(3) 0.53025(17) 0.1265(14) Uani 1 1 d . . .
O1 O -0.09983(19) 0.18604(19) 0.40995(9) 0.0535(6) Uani 1 1 d . . .
N1 N -0.0261(3) 0.0933(2) 0.58595(13) 0.0607(8) Uani 1 1 d . . .
H1B H -0.0737 0.0419 0.5943 0.073 Uiso 1 1 calc R . .
N2 N 0.0401(2) 0.2802(2) 0.46039(11) 0.0465(7) Uani 1 1 d . . .
H2A H 0.0886 0.3325 0.4563 0.056 Uiso 1 1 calc R . .
N3 N -0.0211(2) 0.3374(2) 0.36619(12) 0.0469(7) Uani 1 1 d . . .
H3B H 0.0297 0.3875 0.3704 0.056 Uiso 1 1 calc R . .
C1 C -0.0330(3) 0.1416(3) 0.53070(16) 0.0526(9) Uani 1 1 d . . .
H1A H -0.0891 0.1205 0.5027 0.063 Uiso 1 1 calc R . .
C2 C 0.0436(2) 0.2228(3) 0.51563(14) 0.0418(8) Uani 1 1 d . . .
C3 C 0.1252(3) 0.2514(3) 0.55987(15) 0.0493(8) Uani 1 1 d . . .
H3A H 0.1782 0.3059 0.5512 0.059 Uiso 1 1 calc R . .
C4 C 0.1280(3) 0.1999(3) 0.61584(17) 0.0574(9) Uani 1 1 d . . .
H4A H 0.1829 0.2192 0.6450 0.069 Uiso 1 1 calc R . .
C5 C 0.0509(3) 0.1208(3) 0.62868(17) 0.0608(10) Uani 1 1 d . . .
H5A H 0.0516 0.0860 0.6668 0.073 Uiso 1 1 calc R . .
C6 C -0.0324(3) 0.2623(3) 0.41191(14) 0.0447(8) Uani 1 1 d . . .
C7 C -0.0891(3) 0.3372(2) 0.31171(14) 0.0420(8) Uani 1 1 d . . .
C8 C -0.0826(3) 0.2511(3) 0.27015(15) 0.0504(9) Uani 1 1 d . . .
C9 C -0.1532(3) 0.2544(3) 0.21849(17) 0.0677(11) Uani 1 1 d . . .
H9A H -0.1520 0.1967 0.1907 0.081 Uiso 1 1 calc R . .
C10 C -0.2239(3) 0.3406(4) 0.20784(17) 0.0716(11) Uani 1 1 d . . .
H10A H -0.2704 0.3411 0.1730 0.086 Uiso 1 1 calc R . .
C11 C -0.2271(3) 0.4270(3) 0.24820(19) 0.0646(10) Uani 1 1 d . . .
H11A H -0.2735 0.4867 0.2396 0.077 Uiso 1 1 calc R . .
C12 C -0.1620(3) 0.4258(3) 0.30152(16) 0.0509(9) Uani 1 1 d . . .
C13 C -0.0001(3) 0.1582(3) 0.27853(17) 0.0699(11) Uani 1 1 d . . .
H13A H 0.0422 0.1682 0.3161 0.105 Uiso 1 1 calc R . .
H13B H 0.0521 0.1560 0.2443 0.105 Uiso 1 1 calc R . .
H13C H -0.0420 0.0910 0.2805 0.105 Uiso 1 1 calc R . .
C14 C -0.1721(3) 0.5169(3) 0.34746(17) 0.0676(11) Uani 1 1 d . . .
H14A H -0.2253 0.5703 0.3323 0.101 Uiso 1 1 calc R . .
H14B H -0.0984 0.5501 0.3533 0.101 Uiso 1 1 calc R . .
H14C H -0.1992 0.4886 0.3861 0.101 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'
Cl Cl 0.1484 0.1585 '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
O5 Cl O4 113.7(3) . . ?
O5 Cl O2 109.3(2) . . ?
O4 Cl O2 108.1(2) . . ?
O5 Cl O3 108.1(2) . . ?
O4 Cl O3 107.92(18) . . ?
O2 Cl O3 109.8(2) . . ?
C5 N1 C1 123.3(3) . . ?
C5 N1 H1B 118.3 . . ?
C1 N1 H1B 118.3 . . ?
C6 N2 C2 126.8(3) . . ?
C6 N2 H2A 116.6 . . ?
C2 N2 H2A 116.6 . . ?
C6 N3 C7 123.4(2) . . ?
C6 N3 H3B 118.3 . . ?
C7 N3 H3B 118.3 . . ?
N1 C1 C2 119.6(3) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C1 C2 N2 123.5(3) . . ?
C1 C2 C3 117.4(3) . . ?
N2 C2 C3 119.0(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
N1 C5 C4 119.1(3) . . ?
N1 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
O1 C6 N3 123.8(3) . . ?
O1 C6 N2 123.2(3) . . ?
N3 C6 N2 113.0(3) . . ?
C8 C7 C12 121.5(3) . . ?
C8 C7 N3 120.6(3) . . ?
C12 C7 N3 117.9(3) . . ?
C9 C8 C7 117.9(3) . . ?
C9 C8 C13 119.8(3) . . ?
C7 C8 C13 122.2(3) . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 H9A 119.4 . . ?
C8 C9 H9A 119.4 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C7 118.3(3) . . ?
C11 C12 C14 120.1(3) . . ?
C7 C12 C14 121.5(3) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
Cl O5 1.380(3) . ?
Cl O4 1.403(3) . ?
Cl O2 1.415(3) . ?
Cl O3 1.434(3) . ?
O1 C6 1.224(4) . ?
N1 C5 1.333(4) . ?
N1 C1 1.339(4) . ?
N1 H1B 0.8600 . ?
N2 C6 1.366(4) . ?
N2 C2 1.390(4) . ?
N2 H2A 0.8600 . ?
N3 C6 1.360(4) . ?
N3 C7 1.422(4) . ?
N3 H3B 0.8600 . ?
C1 C2 1.378(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.396(4) . ?
C3 C4 1.368(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.352(5) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C7 C8 1.391(4) . ?
C7 C12 1.399(5) . ?
C8 C9 1.390(5) . ?
C8 C13 1.504(5) . ?
C9 C10 1.361(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.376(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11A 0.9300 . ?
C12 C14 1.503(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
C1 H1A O1 0.93 2.17 2.784(4) 122.9 .
C3 H3A O1 0.93 2.72 3.361(4) 126.5 4_556
C13 H13A O1 0.96 2.63 3.095(4) 110.1 .
N3 H3B O2 0.86 2.21 3.037(4) 160.0 4_556
C14 H14B O2 0.96 2.58 3.454(5) 150.9 4_556
N1 H1B O3 0.86 2.00 2.853(4) 171.8 .
N1 H1B O4 0.86 2.79 3.289(4) 118.2 .
N2 H2A O4 0.86 2.23 3.072(5) 166.5 4_556
C1 H1A O4 0.93 2.54 3.173(4) 125.5 .
C3 H3A O4 0.93 2.66 3.433(5) 140.7 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
C5 N1 C1 C2 1.2(5) . . . . ?
N1 C1 C2 N2 -177.5(3) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
C6 N2 C2 C1 -4.2(5) . . . . ?
C6 N2 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
N2 C2 C3 C4 177.1(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C1 N1 C5 C4 -1.4(5) . . . . ?
C3 C4 C5 N1 0.9(5) . . . . ?
C7 N3 C6 O1 1.9(5) . . . . ?
C7 N3 C6 N2 -178.5(3) . . . . ?
C2 N2 C6 O1 -5.2(5) . . . . ?
C2 N2 C6 N3 175.1(3) . . . . ?
C6 N3 C7 C8 -63.7(4) . . . . ?
C6 N3 C7 C12 116.3(3) . . . . ?
C12 C7 C8 C9 -1.5(5) . . . . ?
N3 C7 C8 C9 178.5(3) . . . . ?
C12 C7 C8 C13 176.6(3) . . . . ?
N3 C7 C8 C13 -3.5(5) . . . . ?
C7 C8 C9 C10 1.9(5) . . . . ?
C13 C8 C9 C10 -176.1(3) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -2.5(6) . . . . ?
C10 C11 C12 C7 2.9(5) . . . . ?
C10 C11 C12 C14 -175.8(3) . . . . ?
C8 C7 C12 C11 -0.9(5) . . . . ?
N3 C7 C12 C11 179.1(3) . . . . ?
C8 C7 C12 C14 177.8(3) . . . . ?
N3 C7 C12 C14 -2.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149167
