#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:30:50 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185252 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/57/7225746.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_7225746
loop_
_publ_author_name
'Saunders, Lucy K.'
'Nowell, Harriott'
'Raithby, Paul R.'
'Wilson, Chick C.'
_publ_section_title
;
 Crystal engineering urea organic acid hydrogen bonded networks with
 solvent inclusion properties
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5916
_journal_paper_doi               10.1039/C6CE00872K
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C8 H5 N1 O6, 2(C7 H8 N2 O1)'
_chemical_formula_sum            'C22 H21 N5 O8'
_chemical_formula_weight         483.44
_chemical_name_systematic        'bis(n-phenylurea) 5-nitroisophthalic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                71.440(7)
_cell_angle_beta                 78.479(7)
_cell_angle_gamma                83.019(7)
_cell_formula_units_Z            2
_cell_length_a                   8.9131(7)
_cell_length_b                   9.7105(8)
_cell_length_c                   13.3778(11)
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.7230
_cell_measurement_theta_min      3.6530
_cell_volume                     1073.43(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1468
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8876
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.343
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular needle'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+0.0588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3277
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00872k2.cif
_cod_data_source_block           NS1
_cod_depositor_comments
'Adding full bibliography for 7225737--7225747.cif.'
_cod_database_code               7225746
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
H2 H 0.320(2) 0.889(2) 0.1777(14) 0.015(5) Uiso 1 1 d
H4 H 0.663(2) 0.575(2) 0.1974(14) 0.019(5) Uiso 1 1 d
H5 H 0.669(2) 0.469(2) 0.0169(16) 0.024(5) Uiso 1 1 d
H13 H 0.723(3) 0.089(3) 0.307(2) 0.054(8) Uiso 1 1 d
H3 H 0.224(2) 0.469(2) 0.3159(15) 0.028(6) Uiso 1 1 d
H6 H 0.577(2) 0.707(2) -0.0554(15) 0.026(6) Uiso 1 1 d
H20 H 0.232(3) 0.013(2) 0.4087(17) 0.036(6) Uiso 1 1 d
H16 H 0.502(2) -0.356(2) 0.4846(16) 0.029(6) Uiso 1 1 d
H17 H 0.277(2) -0.488(2) 0.5564(15) 0.029(6) Uiso 1 1 d
H15 H 0.492(3) 0.021(3) 0.3875(17) 0.035(7) Uiso 1 1 d
H10 H 1.036(3) 0.328(2) -0.0552(17) 0.035(6) Uiso 1 1 d
H7 H 0.723(2) 0.866(2) -0.1948(16) 0.030(6) Uiso 1 1 d
H11 H 1.043(3) 0.108(3) 0.0601(18) 0.046(7) Uiso 1 1 d
H9 H 1.060(3) 0.550(2) -0.1994(16) 0.032(6) Uiso 1 1 d
H14 H 0.856(3) -0.028(3) 0.2900(18) 0.040(7) Uiso 1 1 d
H19 H 0.016(2) -0.112(2) 0.4773(16) 0.031(6) Uiso 1 1 d
H18 H 0.036(3) -0.372(2) 0.5571(16) 0.038(6) Uiso 1 1 d
H8 H 0.972(2) 0.790(2) -0.2713(16) 0.032(6) Uiso 1 1 d
H12 H 0.906(3) 0.014(3) 0.0916(19) 0.054(8) Uiso 1 1 d
H1 H 0.640(3) 1.076(3) 0.0769(19) 0.060(8) Uiso 1 1 d
H21 H -0.115(3) 0.699(3) 0.3336(19) 0.056(8) Uiso 1 1 d
O5 O 0.04677(15) 0.87650(15) 0.23154(11) 0.0283(3) Uani 1 1 d
O3 O 0.76014(15) 0.83561(15) 0.09876(11) 0.0273(3) Uani 1 1 d
O4 O 0.56242(16) 0.99881(15) 0.11389(12) 0.0292(4) Uani 1 1 d
O6 O -0.01631(16) 0.64858(15) 0.32100(11) 0.0251(3) Uani 1 1 d
O1 O 0.70806(15) -0.24088(15) 0.37213(11) 0.0272(3) Uani 1 1 d
O7 O 0.40809(17) 0.26197(15) 0.34874(11) 0.0288(4) Uani 1 1 d
C10 C 0.2458(2) 0.6903(2) 0.24912(14) 0.0176(4) Uani 1 1 d
N2 N 0.5145(2) -0.0706(2) 0.39569(13) 0.0232(4) Uani 1 1 d
N1 N 0.49922(19) 0.35101(18) 0.28901(13) 0.0230(4) Uani 1 1 d
N3 N 0.7585(2) -0.0029(2) 0.32127(15) 0.0285(4) Uani 1 1 d
O8 O 0.63201(17) 0.31703(16) 0.25320(12) 0.0339(4) Uani 1 1 d
C13 C 0.5091(2) 0.7531(2) 0.17833(14) 0.0177(4) Uani 1 1 d
C9 C 0.2926(2) 0.5443(2) 0.28113(15) 0.0184(4) Uani 1 1 d
C8 C 0.4478(2) 0.5060(2) 0.25896(14) 0.0180(4) Uani 1 1 d
C14 C 0.5570(2) 0.6066(2) 0.20850(15) 0.0196(4) Uani 1 1 d
C15 C 0.6239(2) 0.8661(2) 0.12615(15) 0.0207(4) Uani 1 1 d
C11 C 0.0824(2) 0.7472(2) 0.26609(15) 0.0191(4) Uani 1 1 d
C3 C 0.4012(2) -0.3088(2) 0.48455(16) 0.0239(5) Uani 1 1 d
C12 C 0.3538(2) 0.7937(2) 0.19778(15) 0.0183(4) Uani 1 1 d
C2 C 0.3875(2) -0.1588(2) 0.43943(14) 0.0195(4) Uani 1 1 d
C1 C 0.6633(2) -0.1118(2) 0.36341(15) 0.0204(4) Uani 1 1 d
C7 C 0.2419(2) -0.0875(2) 0.43850(16) 0.0239(5) Uani 1 1 d
C5 C 0.1254(2) -0.3148(2) 0.52606(17) 0.0269(5) Uani 1 1 d
C4 C 0.2697(3) -0.3853(2) 0.52755(17) 0.0269(5) Uani 1 1 d
C6 C 0.1121(3) -0.1656(3) 0.48104(17) 0.0272(5) Uani 1 1 d
O2 O 0.71819(15) 0.21895(14) 0.02326(11) 0.0255(3) Uani 1 1 d
N5 N 0.9370(2) 0.34228(18) -0.04400(13) 0.0219(4) Uani 1 1 d
N4 N 0.9447(2) 0.1068(2) 0.06413(14) 0.0266(4) Uani 1 1 d
C16 C 0.8595(2) 0.2216(2) 0.01538(14) 0.0184(4) Uani 1 1 d
C17 C 0.8732(2) 0.4848(2) -0.08419(15) 0.0193(4) Uani 1 1 d
C18 C 0.7288(2) 0.5323(2) -0.04115(16) 0.0224(5) Uani 1 1 d
C21 C 0.9626(2) 0.5821(2) -0.16858(16) 0.0237(5) Uani 1 1 d
C19 C 0.6740(3) 0.6753(2) -0.08318(17) 0.0271(5) Uani 1 1 d
C20 C 0.7626(3) 0.7709(2) -0.16720(17) 0.0291(5) Uani 1 1 d
C22 C 0.9070(3) 0.7245(2) -0.20938(17) 0.0270(5) 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
C9 C10 C12 119.91(18)
C9 C10 C11 123.78(17)
C12 C10 C11 116.31(18)
C1 N2 C2 128.33(18)
O7 N1 O8 123.42(17)
O7 N1 C8 118.57(16)
O8 N1 C8 118.00(16)
C14 C13 C12 119.29(17)
C14 C13 C15 120.29(17)
C12 C13 C15 120.42(18)
C10 C9 C8 117.90(17)
C14 C8 C9 123.17(19)
C14 C8 N1 118.10(18)
C9 C8 N1 118.72(16)
C8 C14 C13 118.49(18)
O3 C15 O4 124.59(17)
O3 C15 C13 122.79(19)
O4 C15 C13 112.62(16)
O5 C11 O6 123.82(18)
O5 C11 C10 121.01(17)
O6 C11 C10 115.17(17)
C2 C3 C4 119.4(2)
C13 C12 C10 121.22(19)
C3 C2 C7 119.50(18)
C3 C2 N2 123.69(19)
C7 C2 N2 116.79(18)
O1 C1 N3 122.25(19)
O1 C1 N2 122.58(17)
N3 C1 N2 115.17(19)
C6 C7 C2 120.3(2)
C6 C5 C4 119.3(2)
C5 C4 C3 121.2(2)
C5 C6 C7 120.3(2)
C16 N5 C17 126.92(17)
O2 C16 N4 122.15(18)
O2 C16 N5 122.14(19)
N4 C16 N5 115.71(18)
C18 C17 C21 119.44(19)
C18 C17 N5 122.80(17)
C21 C17 N5 117.72(18)
C17 C18 C19 119.9(2)
C22 C21 C17 120.1(2)
C20 C19 C18 120.4(2)
C22 C20 C19 119.9(2)
C20 C22 C21 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C11 1.217(2)
O3 C15 1.225(2)
O4 C15 1.311(2)
O6 C11 1.315(2)
O1 C1 1.244(2)
O7 N1 1.232(2)
C10 C9 1.382(3)
C10 C12 1.392(3)
C10 C11 1.494(3)
N2 C1 1.363(2)
N2 C2 1.417(2)
N1 O8 1.232(2)
N1 C8 1.469(2)
N3 C1 1.343(2)
C13 C14 1.387(3)
C13 C12 1.389(3)
C13 C15 1.496(2)
C9 C8 1.386(3)
C8 C14 1.380(3)
C3 C2 1.388(3)
C3 C4 1.388(3)
C2 C7 1.395(3)
C7 C6 1.384(3)
C5 C6 1.381(3)
C5 C4 1.382(3)
O2 C16 1.245(2)
N5 C16 1.367(2)
N5 C17 1.409(3)
N4 C16 1.332(3)
C17 C18 1.389(3)
C17 C21 1.396(3)
C18 C19 1.390(3)
C21 C22 1.384(3)
C19 C20 1.382(3)
C20 C22 1.381(3)
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
C18 H5 O2 0.94(2) 2.39(2) 2.894(2) 113.2(14) .
N3 H13 O8 0.88(3) 2.21(3) 3.084(3) 174(2) .
C3 H16 O1 0.96(2) 2.28(2) 2.888(2) 120.5(16) .
N2 H15 O7 0.86(2) 2.30(3) 3.151(2) 171(2) .
N5 H10 O3 0.87(2) 2.37(2) 3.113(2) 143.4(18) 2_765
N4 H11 O3 0.86(2) 2.43(2) 3.045(2) 129(2) 2_765
N3 H14 O5 0.93(3) 1.98(3) 2.889(3) 168(2) 1_645
N4 H12 O3 0.94(3) 2.25(3) 3.135(2) 156(2) 1_545
O4 H1 O2 1.02(3) 1.53(3) 2.5232(18) 164(2) 1_565
O6 H21 O1 0.96(3) 1.66(3) 2.610(2) 170(2) 1_465
