# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CIM1
_database_code_depnum_ccdc_archive 'CCDC 1471780'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'bis(n-phenylurea) bis(5-nitroisophthalic acid) dihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_moiety_formula         'C8 H5 N1 O6, C7 H8 N2 O, H2 O'
_chemical_formula_sum            'C15 H15 N3 O8'
_chemical_formula_weight         365.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8562(5)
_cell_length_b                   11.9649(9)
_cell_length_c                   20.6362(10)
_cell_angle_alpha                78.951(5)
_cell_angle_beta                 88.870(5)
_cell_angle_gamma                76.106(6)
_cell_volume                     1612.26(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    4514
_cell_measurement_theta_min      3.7850
_cell_measurement_theta_max      71.7780

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_min  0.87429
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            11673
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.878
_diffrn_reflns_theta_max         72.174
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6168
_reflns_number_gt                5069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

The hydrogen atoms of each water molecule were fixed at a standard O--H length of 0.82 Angstroms. 
In one of the water molecules, the HOH angle was fixed using a DANG between H102 and H103 and the thermal
parameters of H102 and H103 were fixed at -1.5.

The 5-nitroisophthalic acid hydroxyl groups were fixed in riding positions, using HFIX 83. 

The aromatic c--H groups and tertiary amine N--H groups were fixed in riding positions using HFIX 43, on 5-nitroisophthalic acid
and n-phenylurea. 

The primary amine N--H groups were fixed in riding positions using HFIX 93. 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1186P)²+3.0543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6168
_refine_ls_number_parameters     483
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0848
_refine_ls_wR_factor_ref         0.2446
_refine_ls_wR_factor_gt          0.2353
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H101 H 0.447(7) 0.318(4) 0.250(2) 0.031(13) Uiso 1 1 d . . . . .
H100 H 0.462(9) 0.422(6) 0.251(3) 0.059(17) Uiso 1 1 d . . . . .
H102 H 0.193(5) 0.315(6) 0.178(3) 0.088 Uiso 1 1 d D U . . .
H103 H 0.331(10) 0.249(4) 0.146(3) 0.088 Uiso 1 1 d D U . . .
O11 O 0.3115(4) 0.5263(2) 0.09875(13) 0.0312(6) Uani 1 1 d . . . . .
H105 H 0.3185 0.4610 0.1212 0.047 Uiso 1 1 calc R U . . .
O10 O 0.3391(4) 0.5745(2) 0.19683(13) 0.0330(6) Uani 1 1 d . . . . .
O13 O 0.1992(4) 1.0055(2) -0.09840(13) 0.0319(6) Uani 1 1 d . . . . .
H13 H 0.1776 1.0170 -0.1384 0.048 Uiso 1 1 calc R U . . .
O12 O 0.2200(6) 0.8183(3) -0.10578(14) 0.0453(8) Uani 1 1 d . . . . .
C30 C 0.3223(5) 0.5995(3) 0.13718(17) 0.0232(7) Uani 1 1 d . . . . .
O8 O 0.3221(5) 1.1092(2) 0.10585(15) 0.0407(7) Uani 1 1 d . . . . .
C5 C 0.3105(5) 0.7211(3) 0.10039(18) 0.0239(7) Uani 1 1 d . . . . .
O9 O 0.3900(6) 0.9789(3) 0.19720(15) 0.0492(9) Uani 1 1 d . . . . .
C4 C 0.2803(5) 0.7496(3) 0.03232(18) 0.0242(7) Uani 1 1 d . . . . .
H4 H 0.2689 0.6923 0.0089 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3201(5) 0.9169(3) 0.10183(18) 0.0250(7) Uani 1 1 d . . . . .
N1 N 0.3450(5) 1.0078(3) 0.13825(16) 0.0320(7) Uani 1 1 d . . . . .
C6 C 0.3308(5) 0.8050(3) 0.13630(17) 0.0238(7) Uani 1 1 d . . . . .
H6 H 0.3509 0.7862 0.1819 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2672(5) 0.8637(3) -0.00078(18) 0.0249(7) Uani 1 1 d . . . . .
C2 C 0.2862(5) 0.9497(3) 0.03450(18) 0.0243(7) Uani 1 1 d . . . . .
H2 H 0.2762 1.0267 0.0131 0.029 Uiso 1 1 calc R U . . .
C29 C 0.2263(6) 0.8940(3) -0.07375(19) 0.0276(8) Uani 1 1 d . . . . .
O14 O 1.0117(4) 0.3239(2) 0.25087(12) 0.0285(6) Uani 1 1 d . . . . .
N3 N 0.9069(5) 0.3931(3) 0.34278(16) 0.0314(7) Uani 1 1 d . . . . .
H3A H 0.9619 0.3269 0.3676 0.038 Uiso 1 1 calc R U . . .
H3B H 0.8434 0.4508 0.3602 0.038 Uiso 1 1 calc R U . . .
N2 N 0.8322(5) 0.5134(3) 0.24184(15) 0.0254(7) Uani 1 1 d . . . . .
H2A H 0.7713 0.5647 0.2641 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8282(5) 0.5510(3) 0.17259(18) 0.0237(7) Uani 1 1 d . . . . .
C20 C 0.9203(5) 0.4064(3) 0.27724(18) 0.0237(7) Uani 1 1 d . . . . .
C12 C 0.8148(6) 0.4784(3) 0.12836(19) 0.0270(8) Uani 1 1 d . . . . .
H12 H 0.8117 0.4006 0.1439 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8291(5) 0.6680(3) 0.14863(19) 0.0256(7) Uani 1 1 d . . . . .
H8 H 0.8373 0.7170 0.1780 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8179(6) 0.7115(3) 0.0814(2) 0.0302(8) Uani 1 1 d . . . . .
H9 H 0.8170 0.7898 0.0658 0.036 Uiso 1 1 calc R U . . .
C10 C 0.8078(6) 0.6395(4) 0.03712(19) 0.0333(9) Uani 1 1 d . . . . .
H10 H 0.8023 0.6687 -0.0081 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8061(6) 0.5230(4) 0.0610(2) 0.0324(8) Uani 1 1 d . . . . .
H11 H 0.7990 0.4743 0.0315 0.039 Uiso 1 1 calc R U . . .
O3 O 0.6633(5) 0.1279(2) 0.38611(13) 0.0350(7) Uani 1 1 d . . . . .
O6 O 0.4229(4) 0.2787(3) 0.69734(13) 0.0349(7) Uani 1 1 d . . . . .
O7 O 0.3574(5) 0.4085(2) 0.60732(15) 0.0370(7) Uani 1 1 d . . . . .
O1 O 0.9168(5) -0.0760(2) 0.21737(13) 0.0363(7) Uani 1 1 d . . . . .
O5 O 0.8075(5) -0.1172(2) 0.68784(13) 0.0339(7) Uani 1 1 d . . . . .
H5 H 0.8659 -0.1857 0.7019 0.051 Uiso 1 1 calc R U . . .
O4 O 0.8722(5) -0.1684(2) 0.58937(14) 0.0394(7) Uani 1 1 d . . . . .
O2 O 0.5000(5) 0.3088(2) 0.39502(13) 0.0338(6) Uani 1 1 d . . . . .
H2B H 0.5002 0.3198 0.3546 0.051 Uiso 1 1 calc R U . . .
N6 N 0.4277(4) 0.3083(3) 0.63726(16) 0.0263(7) Uani 1 1 d . . . . .
C18 C 1.1420(6) -0.4176(3) 0.4221(2) 0.0330(9) Uani 1 1 d . . . . .
H18 H 1.2009 -0.4936 0.4439 0.040 Uiso 1 1 calc R U . . .
C24 C 0.6107(5) 0.1079(3) 0.63110(17) 0.0220(7) Uani 1 1 d . . . . .
H24 H 0.6127 0.0879 0.6769 0.026 Uiso 1 1 calc R U . . .
C28 C 0.8018(5) -0.0970(3) 0.62327(18) 0.0249(7) Uani 1 1 d . . . . .
C14 C 0.9658(5) -0.1900(3) 0.35594(17) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.9585(5) -0.2205(3) 0.42461(18) 0.0254(7) Uani 1 1 d . . . . .
H19 H 0.8946 -0.1643 0.4485 0.031 Uiso 1 1 calc R U . . .
C15 C 1.0644(5) -0.2750(3) 0.32056(18) 0.0259(7) Uani 1 1 d . . . . .
H15 H 1.0725 -0.2563 0.2749 0.031 Uiso 1 1 calc R U . . .
C26 C 0.6913(5) 0.0578(3) 0.52447(17) 0.0240(7) Uani 1 1 d . . . . .
H26 H 0.7498 0.0024 0.4994 0.029 Uiso 1 1 calc R U . . .
N4 N 0.8748(5) -0.0732(3) 0.32738(15) 0.0263(7) Uani 1 1 d . . . . .
H4A H 0.8242 -0.0287 0.3547 0.032 Uiso 1 1 calc R U . . .
C23 C 0.5214(5) 0.2201(3) 0.59832(18) 0.0221(7) Uani 1 1 d . . . . .
C25 C 0.6975(5) 0.0262(3) 0.59288(17) 0.0223(7) Uani 1 1 d . . . . .
N5 N 0.7680(5) 0.0940(3) 0.24937(16) 0.0333(8) Uani 1 1 d . . . . .
H5A H 0.7524 0.1318 0.2092 0.040 Uiso 1 1 calc R U . . .
H5B H 0.7271 0.1301 0.2812 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8553(6) -0.0202(3) 0.26225(18) 0.0263(8) Uani 1 1 d . . . . .
C21 C 0.5989(5) 0.1712(3) 0.49301(17) 0.0228(7) Uani 1 1 d . . . . .
C22 C 0.5133(5) 0.2540(3) 0.53025(18) 0.0234(7) Uani 1 1 d . . . . .
H22 H 0.4519 0.3305 0.5101 0.028 Uiso 1 1 calc R U . . .
C27 C 0.5912(6) 0.1998(3) 0.41916(18) 0.0252(7) Uani 1 1 d . . . . .
C16 C 1.1499(6) -0.3876(3) 0.3546(2) 0.0293(8) Uani 1 1 d . . . . .
H16 H 1.2143 -0.4443 0.3311 0.035 Uiso 1 1 calc R U . . .
C17 C 1.0455(6) -0.3337(4) 0.45752(19) 0.0304(8) Uani 1 1 d . . . . .
H17 H 1.0390 -0.3532 0.5032 0.036 Uiso 1 1 calc R U . . .
O16 O 0.5046(5) 0.3508(3) 0.26890(15) 0.0385(7) Uani 1 1 d . . . . .
O15 O 0.3075(5) 0.3089(3) 0.16296(14) 0.0349(7) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O11 C30 1.304(5) . ?
O10 C30 1.211(4) . ?
O13 C29 1.304(5) . ?
O12 C29 1.228(5) . ?
C30 C5 1.491(5) . ?
O8 N1 1.244(4) . ?
C5 C4 1.388(5) . ?
C5 C6 1.390(5) . ?
O9 N1 1.223(5) . ?
C4 C3 1.386(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.378(5) . ?
C1 N1 1.478(5) . ?
C3 C2 1.401(5) . ?
C3 C29 1.495(5) . ?
O14 C20 1.248(4) . ?
N3 C20 1.335(5) . ?
N2 C20 1.351(5) . ?
N2 C7 1.412(5) . ?
C7 C12 1.393(5) . ?
C7 C8 1.394(5) . ?
C12 C11 1.387(6) . ?
C8 C9 1.382(5) . ?
C9 C10 1.384(6) . ?
C10 C11 1.389(6) . ?
O3 C27 1.207(5) . ?
O6 N6 1.224(4) . ?
O7 N6 1.226(4) . ?
O1 C13 1.252(5) . ?
O5 C28 1.308(4) . ?
O4 C28 1.212(5) . ?
O2 C27 1.307(4) . ?
N6 C23 1.466(4) . ?
C18 C16 1.373(6) . ?
C18 C17 1.387(6) . ?
C24 C23 1.381(5) . ?
C24 C25 1.389(5) . ?
C28 C25 1.495(5) . ?
C14 C19 1.397(5) . ?
C14 C15 1.400(5) . ?
C14 N4 1.404(5) . ?
C19 C17 1.388(5) . ?
C15 C16 1.388(5) . ?
C26 C25 1.388(5) . ?
C26 C21 1.388(5) . ?
N4 C13 1.366(5) . ?
C23 C22 1.384(5) . ?
N5 C13 1.331(5) . ?
C21 C22 1.383(5) . ?
C21 C27 1.496(5) . ?

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
O10 C30 O11 125.1(3) . . ?
O10 C30 C5 121.7(3) . . ?
O11 C30 C5 113.2(3) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 C30 121.0(3) . . ?
C6 C5 C30 118.0(3) . . ?
C3 C4 C5 120.0(3) . . ?
C6 C1 C2 123.4(3) . . ?
C6 C1 N1 119.0(3) . . ?
C2 C1 N1 117.6(3) . . ?
O9 N1 O8 124.4(3) . . ?
O9 N1 C1 118.8(3) . . ?
O8 N1 C1 116.9(3) . . ?
C1 C6 C5 117.5(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 C29 119.3(3) . . ?
C2 C3 C29 120.8(3) . . ?
C1 C2 C3 118.1(3) . . ?
O12 C29 O13 124.9(3) . . ?
O12 C29 C3 121.4(3) . . ?
O13 C29 C3 113.7(3) . . ?
C20 N2 C7 127.7(3) . . ?
C12 C7 C8 119.6(3) . . ?
C12 C7 N2 123.1(3) . . ?
C8 C7 N2 117.3(3) . . ?
O14 C20 N3 121.1(3) . . ?
O14 C20 N2 122.5(3) . . ?
N3 C20 N2 116.4(3) . . ?
C11 C12 C7 119.6(4) . . ?
C9 C8 C7 120.1(3) . . ?
C8 C9 C10 120.6(4) . . ?
C9 C10 C11 119.2(4) . . ?
C12 C11 C10 120.8(4) . . ?
O6 N6 O7 123.5(3) . . ?
O6 N6 C23 119.0(3) . . ?
O7 N6 C23 117.5(3) . . ?
C16 C18 C17 119.4(4) . . ?
C23 C24 C25 117.4(3) . . ?
O4 C28 O5 125.3(3) . . ?
O4 C28 C25 121.2(3) . . ?
O5 C28 C25 113.5(3) . . ?
C19 C14 C15 119.1(3) . . ?
C19 C14 N4 116.4(3) . . ?
C15 C14 N4 124.5(3) . . ?
C17 C19 C14 120.7(3) . . ?
C16 C15 C14 119.0(3) . . ?
C25 C26 C21 120.9(3) . . ?
C13 N4 C14 129.0(3) . . ?
C24 C23 C22 123.5(3) . . ?
C24 C23 N6 118.7(3) . . ?
C22 C23 N6 117.8(3) . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 C28 117.8(3) . . ?
C24 C25 C28 121.8(3) . . ?
O1 C13 N5 122.0(3) . . ?
O1 C13 N4 121.8(3) . . ?
N5 C13 N4 116.1(3) . . ?
C22 C21 C26 119.6(3) . . ?
C22 C21 C27 121.6(3) . . ?
C26 C21 C27 118.8(3) . . ?
C21 C22 C23 118.3(3) . . ?
O3 C27 O2 124.4(3) . . ?
O3 C27 C21 122.2(3) . . ?
O2 C27 C21 113.4(3) . . ?
C18 C16 C15 121.8(4) . . ?
C18 C17 C19 119.9(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
O16 H100 O10 0.85(7) 1.95(7) 2.783(4) 169(6) .
O15 H102 O14 0.83(2) 1.93(4) 2.691(4) 151(7) 1_455
O15 H103 O8 0.84(2) 2.02(3) 2.840(4) 167(6) 1_545
O11 H105 O15 0.82 1.88 2.690(4) 171.3 .
O13 H13 O1 0.82 1.72 2.516(4) 163.4 2_665
N3 H3A O4 0.86 2.01 2.858(4) 168.6 2_756
N3 H3B O7 0.86 2.11 2.962(4) 169.7 2_666
N2 H2A O6 0.86 2.29 3.137(4) 168.0 2_666
O5 H5 O14 0.82 1.77 2.578(4) 167.5 2_756
O2 H2B O16 0.82 1.74 2.555(4) 176.6 .
C24 H24 O9 0.93 2.57 3.496(5) 176.4 2_666
C15 H15 O1 0.93 2.27 2.865(5) 121.1 .
N4 H4A O3 0.86 2.14 2.955(4) 157.2 .
N5 H5A O12 0.86 2.12 2.954(4) 163.2 2_665
N5 H5B O3 0.86 2.20 2.977(4) 150.8 .

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.104

_shelxl_version_number           2014-3


_chemical_formula_moiety         "'C8 H5 N1 O6, C7 H8 N2 O1, H2 O1"
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CIM2
_database_code_depnum_ccdc_archive 'CCDC 1471781'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'n-phenylurea 5-nitroisophthalic acid acetone solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N2 O1, C8 H5 N1 O6, C3 H6 O1'
_chemical_formula_sum            'C18 H19 N3 O8'
_chemical_formula_weight         405.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.77870(10)
_cell_length_b                   18.8747(2)
_cell_length_c                   13.03430(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.5280(10)
_cell_angle_gamma                90
_cell_volume                     1913.02(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7666
_cell_measurement_theta_min      4.6900
_cell_measurement_theta_max      71.7470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_T_min  0.94218
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            12893
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.123
_diffrn_reflns_theta_max         71.919
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3711
_reflns_number_gt                3376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.2953P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3711
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H4 H 0.0826(16) 0.9272(7) 1.0995(10) 0.022(3) Uiso 1 1 d . . . . .
H9 H -0.4827(18) 0.9518(8) 1.1829(10) 0.027(3) Uiso 1 1 d . . . . .
H5 H 0.0142(17) 0.7148(7) 1.0689(10) 0.024(3) Uiso 1 1 d . . . . .
H8 H -0.5891(19) 0.8984(8) 1.2359(11) 0.030(4) Uiso 1 1 d . . . . .
H2 H 0.2939(19) 0.8218(7) 0.8604(12) 0.033(4) Uiso 1 1 d . . . . .
H10 H -0.586(2) 0.6689(8) 1.1967(13) 0.046(4) Uiso 1 1 d . . . . .
H11 H -0.532(2) 0.5584(10) 1.1175(14) 0.055(5) Uiso 1 1 d . . . . .
H13 H -0.291(2) 0.6616(9) 0.8881(14) 0.049(5) Uiso 1 1 d . . . . .
H7 H -0.5752(19) 0.7865(7) 1.1954(11) 0.028(3) Uiso 1 1 d . . . . .
H6 H -0.346(2) 0.7710(9) 0.9657(12) 0.040(4) Uiso 1 1 d . . . . .
H12 H -0.385(2) 0.5557(9) 0.9611(13) 0.049(4) Uiso 1 1 d . . . . .
H16 H -0.084(3) 0.5092(11) 0.8918(16) 0.065(6) Uiso 1 1 d . . . . .
H18 H 0.294(3) 0.4295(12) 0.7022(17) 0.077(6) Uiso 1 1 d . . . . .
H1 H 0.155(3) 0.5968(11) 0.9041(15) 0.063(5) Uiso 1 1 d . . . . .
H3 H 0.299(2) 1.0499(10) 0.9718(15) 0.067(6) Uiso 1 1 d . . . . .
H15 H -0.059(3) 0.4256(13) 0.8872(18) 0.083(7) Uiso 1 1 d . . . . .
H17 H 0.089(3) 0.4186(12) 0.6722(18) 0.085(7) Uiso 1 1 d . . . . .
H14 H -0.145(3) 0.4633(13) 0.794(2) 0.098(8) Uiso 1 1 d . . . . .
H19 H 0.172(3) 0.3772(12) 0.7572(18) 0.078(7) Uiso 1 1 d . . . . .
O3 O 0.26327(10) 0.69253(4) 0.81557(6) 0.02692(19) Uani 1 1 d . . . . .
O4 O 0.12758(11) 0.63479(4) 0.93913(6) 0.0295(2) Uani 1 1 d . . . . .
O2 O 0.35613(12) 0.95313(4) 0.85631(6) 0.0340(2) Uani 1 1 d . . . . .
O6 O -0.09120(11) 0.87679(4) 1.23180(6) 0.0318(2) Uani 1 1 d . . . . .
O5 O -0.11004(12) 0.76267(5) 1.22347(7) 0.0354(2) Uani 1 1 d . . . . .
O7 O -0.36189(11) 0.87464(4) 1.05364(6) 0.0284(2) Uani 1 1 d . . . . .
O1 O 0.24617(12) 1.00620(4) 0.99366(7) 0.0358(2) Uani 1 1 d . . . . .
N1 N -0.06258(12) 0.81990(5) 1.19033(7) 0.0250(2) Uani 1 1 d . . . . .
C7 C 0.03553(13) 0.82042(6) 1.09543(8) 0.0210(2) Uani 1 1 d . . . . .
C10 C -0.47021(13) 0.73006(6) 1.08904(8) 0.0228(2) Uani 1 1 d . . . . .
N2 N -0.51143(12) 0.79227(5) 1.14266(7) 0.0242(2) Uani 1 1 d . . . . .
C14 C -0.38309(15) 0.72841(6) 0.99697(9) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.18784(13) 0.69234(6) 0.89614(8) 0.0218(2) Uani 1 1 d . . . . .
C8 C 0.15438(13) 0.75845(5) 0.95523(8) 0.0207(2) Uani 1 1 d . . . . .
C6 C 0.05911(13) 0.75720(6) 1.04389(8) 0.0218(2) Uani 1 1 d . . . . .
C5 C 0.10186(14) 0.88427(6) 1.06257(8) 0.0223(2) Uani 1 1 d . . . . .
C2 C 0.27557(14) 0.95169(6) 0.93504(8) 0.0249(2) Uani 1 1 d . . . . .
N3 N -0.51635(13) 0.90871(5) 1.19023(8) 0.0278(2) Uani 1 1 d . . . . .
C3 C 0.22341(14) 0.82178(6) 0.92074(8) 0.0220(2) Uani 1 1 d . . . . .
C4 C 0.19785(14) 0.88452(5) 0.97385(8) 0.0221(2) Uani 1 1 d . . . . .
C13 C -0.40466(17) 0.60063(7) 0.99397(11) 0.0381(3) Uani 1 1 d . . . . .
C9 C -0.45824(13) 0.85969(5) 1.12562(8) 0.0222(2) Uani 1 1 d . . . . .
C12 C -0.49203(18) 0.60252(7) 1.08490(11) 0.0376(3) Uani 1 1 d . . . . .
C11 C -0.52494(16) 0.66658(6) 1.13210(10) 0.0312(3) Uani 1 1 d . . . . .
C15 C -0.35097(16) 0.66348(7) 0.95077(11) 0.0350(3) Uani 1 1 d . . . . .
O8 O 0.21073(11) 0.52448(4) 0.82579(7) 0.0336(2) Uani 1 1 d . . . . .
C16 C 0.11597(16) 0.47519(6) 0.80267(9) 0.0305(3) Uani 1 1 d . . . . .
C18 C -0.0566(2) 0.46796(9) 0.84893(13) 0.0477(4) Uani 1 1 d . . . . .
C17 C 0.1703(2) 0.42127(8) 0.72607(12) 0.0450(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O3 C1 1.2166(13) . ?
O4 C1 1.3144(13) . ?
O2 C2 1.2168(14) . ?
O6 N1 1.2253(12) . ?
O5 N1 1.2239(13) . ?
O7 C9 1.2487(13) . ?
O1 C2 1.3054(14) . ?
N1 C7 1.4707(14) . ?
C7 C5 1.3833(15) . ?
C7 C6 1.3840(15) . ?
C10 C14 1.3942(16) . ?
C10 C11 1.3945(16) . ?
C10 N2 1.4078(13) . ?
N2 C9 1.3582(14) . ?
C14 C15 1.3910(17) . ?
C1 C8 1.4929(14) . ?
C8 C6 1.3896(15) . ?
C8 C3 1.3900(15) . ?
C5 C4 1.3932(15) . ?
C2 C4 1.4983(14) . ?
N3 C9 1.3379(14) . ?
C3 C4 1.3886(15) . ?
C13 C12 1.382(2) . ?
C13 C15 1.383(2) . ?
C12 C11 1.3836(17) . ?
O8 C16 1.2197(15) . ?
C16 C18 1.493(2) . ?
C16 C17 1.4945(19) . ?

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 N1 O6 123.89(9) . . ?
O5 N1 C7 118.10(9) . . ?
O6 N1 C7 118.01(9) . . ?
C5 C7 C6 123.06(10) . . ?
C5 C7 N1 118.19(9) . . ?
C6 C7 N1 118.74(9) . . ?
C14 C10 C11 119.20(10) . . ?
C14 C10 N2 124.63(10) . . ?
C11 C10 N2 116.15(10) . . ?
C9 N2 C10 128.75(9) . . ?
C15 C14 C10 119.30(11) . . ?
O3 C1 O4 123.79(10) . . ?
O3 C1 C8 122.52(9) . . ?
O4 C1 C8 113.69(9) . . ?
C6 C8 C3 120.18(10) . . ?
C6 C8 C1 121.27(9) . . ?
C3 C8 C1 118.54(9) . . ?
C7 C6 C8 118.00(10) . . ?
C7 C5 C4 118.20(10) . . ?
O2 C2 O1 125.32(10) . . ?
O2 C2 C4 121.68(10) . . ?
O1 C2 C4 113.00(10) . . ?
C4 C3 C8 120.70(10) . . ?
C3 C4 C5 119.86(10) . . ?
C3 C4 C2 119.27(10) . . ?
C5 C4 C2 120.88(9) . . ?
C12 C13 C15 119.20(12) . . ?
O7 C9 N3 122.43(10) . . ?
O7 C9 N2 121.75(10) . . ?
N3 C9 N2 115.82(10) . . ?
C13 C12 C11 120.33(12) . . ?
C12 C11 C10 120.64(12) . . ?
C13 C15 C14 121.32(12) . . ?
O8 C16 C18 120.94(12) . . ?
O8 C16 C17 120.32(12) . . ?
C18 C16 C17 118.74(12) . . ?

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
N3 H9 O2 0.861(15) 2.115(15) 2.9600(13) 166.7(13) 3_577
N3 H8 O3 0.855(16) 2.325(16) 3.0673(13) 145.5(13) 4_476
N3 H8 O8 0.855(16) 2.453(15) 3.0691(13) 129.6(12) 4_476
N2 H7 O3 0.865(15) 2.072(15) 2.9058(12) 161.6(13) 4_476
C14 H6 O7 0.949(16) 2.271(16) 2.8609(14) 119.5(12) .
O4 H1 O8 0.88(2) 1.77(2) 2.6433(12) 175.8(19) .
O1 H3 O7 0.97(2) 1.54(2) 2.5057(11) 171.2(18) 3_577
C18 H15 O4 0.94(2) 2.60(2) 3.4320(17) 147.0(18) 3_567
C18 H14 O2 0.98(3) 2.53(3) 3.511(2) 176(2) 2_546

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM1
_database_code_depnum_ccdc_archive 'CCDC 1471782'
_audit_update_record             
;
2016-06-09 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT355_IM1                 
;
PROBLEM: Long O-H (X0.82,N0.98A) O101 - H107 .. 1.09 Ang.
RESPONSE: The H107 is in a short O-H...O hydrogen bond.
;
_vrf_PLAT910_IM1                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min) 33 Note
RESPONSE: Caused by large unit cell parameters.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Heptakis(n-phenylurea) tetrakis(5-nitroisophthalic acid) dimethanol solvate '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C8 H5 N1 O6), 7(C7 H8 N2 O1), 2(C1 H4 O1)'
_chemical_formula_sum            'C83 H84 N18 O33'
_chemical_formula_weight         1861.68

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.2579(6)
_cell_length_b                   14.7289(9)
_cell_length_c                   23.5050(14)
_cell_angle_alpha                94.490(5)
_cell_angle_beta                 91.215(4)
_cell_angle_gamma                90.291(4)
_cell_volume                     4229.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7587
_cell_measurement_theta_min      3.5900
_cell_measurement_theta_max      27.9220

_exptl_crystal_description       'arrow head'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_min  0.93896
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.1468
_diffrn_reflns_number            37793
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.282
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             16015
_reflns_number_gt                9340
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

H28 was refined with an isotropic thermal parameter fixed at -1.5.
The methyl hydrogen atoms of each methanol solvent were fixed in riding positions using HFIX 137. 
 

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16015
_refine_ls_number_parameters     1518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C200 C 0.6153(2) 0.41105(17) 0.52427(11) 0.0265(6) Uani 1 1 d . . . . .
H1 H 0.8809(19) 0.4373(15) 0.5344(10) 0.027(7) Uiso 1 1 d . . . . .
H2 H 0.549(2) 0.4272(16) 0.5438(11) 0.033(7) Uiso 1 1 d . . . . .
H3 H 0.7054(18) 0.2918(17) 0.4131(11) 0.032(7) Uiso 1 1 d . . . . .
H6 H 0.1787(17) 0.1717(14) 0.0635(9) 0.015(6) Uiso 1 1 d . . . . .
H9 H -0.0285(16) 0.6533(15) 0.2726(10) 0.016(6) Uiso 1 1 d . . . . .
H4 H -0.0048(17) 0.0590(15) -0.0654(10) 0.020(6) Uiso 1 1 d . . . . .
H5 H -0.1540(19) 0.2070(15) 0.0594(10) 0.026(7) Uiso 1 1 d . . . . .
H8 H -0.2174(18) 0.5390(15) 0.1419(10) 0.021(6) Uiso 1 1 d . . . . .
H7 H 0.1171(18) 0.5088(15) 0.1463(10) 0.021(6) Uiso 1 1 d . . . . .
H10 H -0.2415(18) 1.1401(14) 0.5193(10) 0.017(6) Uiso 1 1 d . . . . .
H11 H 0.0825(18) 1.1329(16) 0.4883(11) 0.027(7) Uiso 1 1 d . . . . .
H14 H -0.118(2) 0.9827(17) 0.3542(11) 0.032(8) Uiso 1 1 d . . . . .
H21 H 0.4726(19) 1.1741(16) 0.2875(11) 0.032(7) Uiso 1 1 d . . . . .
H16 H 0.600(2) 0.7145(17) 0.3233(11) 0.032(8) Uiso 1 1 d . . . . .
H18 H 0.7150(19) 0.7982(16) 0.3792(11) 0.032(7) Uiso 1 1 d . . . . .
H13 H -0.2086(18) 1.2314(15) 0.6007(10) 0.023(7) Uiso 1 1 d . . . . .
H12 H -0.040(2) 1.0486(16) 0.4292(11) 0.028(7) Uiso 1 1 d . . . . .
H22 H 0.777(2) 1.2211(17) 0.2315(11) 0.041(8) Uiso 1 1 d . . . . .
H19 H 0.395(2) 0.7820(17) 0.4189(11) 0.035(7) Uiso 1 1 d . . . . .
H20 H 0.434(2) 1.0812(17) 0.2073(11) 0.033(7) Uiso 1 1 d . . . . .
H17 H 0.526(2) 0.6303(18) 0.2515(12) 0.043(9) Uiso 1 1 d . . . . .
H15 H -0.028(2) 1.2774(19) 0.6269(13) 0.047(8) Uiso 1 1 d . . . . .
H23 H 0.4791(17) 0.8836(14) 0.2430(10) 0.018(6) Uiso 1 1 d . . . . .
H28 H 0.0594(19) 0.7614(16) 0.1382(11) 0.027 Uiso 1 1 d . U . . .
H29 H -0.2006(18) 0.7121(17) 0.0738(11) 0.034(7) Uiso 1 1 d . . . . .
H27 H 0.185(2) 0.6847(19) 0.0859(13) 0.046(9) Uiso 1 1 d . . . . .
H25 H 0.3338(19) 1.0152(17) 0.3760(12) 0.033(8) Uiso 1 1 d . . . . .
H24 H 0.1437(19) 0.8609(16) 0.2609(11) 0.033(7) Uiso 1 1 d . . . . .
H26 H 0.150(2) 0.6312(19) 0.0319(13) 0.041(9) Uiso 1 1 d . . . . .
H47 H 1.397(2) 0.5327(16) 0.6679(11) 0.034(7) Uiso 1 1 d . . . . .
H44 H 0.903(2) 0.0765(16) 0.2202(11) 0.032(7) Uiso 1 1 d . . . . .
H46 H 1.388(2) 0.4246(18) 0.5911(12) 0.046(8) Uiso 1 1 d . . . . .
H40 H 0.747(2) 0.8928(18) 0.4616(12) 0.043(8) Uiso 1 1 d . . . . .
H33 H 0.119(2) 1.2306(16) 0.5694(11) 0.036(7) Uiso 1 1 d . . . . .
H45 H 1.052(2) 0.4357(17) 0.5913(11) 0.037(8) Uiso 1 1 d . . . . .
H43 H 1.2691(19) 0.1523(15) 0.2692(10) 0.027(7) Uiso 1 1 d . . . . .
H41 H 1.144(2) 0.2997(16) 0.4424(11) 0.030(7) Uiso 1 1 d . . . . .
H30 H -0.363(2) 0.7731(16) 0.1147(11) 0.031(7) Uiso 1 1 d . . . . .
H32 H -0.0250(19) 0.8498(16) 0.2023(11) 0.029(7) Uiso 1 1 d . . . . .
H37 H 0.6655(18) 0.7606(16) -0.1118(11) 0.024(7) Uiso 1 1 d . . . . .
H42 H 1.275(2) 0.3016(18) 0.4497(12) 0.046(8) Uiso 1 1 d . . . . .
H31 H -0.355(2) 0.8729(18) 0.1936(12) 0.045(9) Uiso 1 1 d . . . . .
H35 H 0.427(2) 0.7152(17) 0.0027(11) 0.037(8) Uiso 1 1 d . . . . .
H38 H 0.761(2) 0.6428(17) -0.0739(12) 0.038(8) Uiso 1 1 d . . . . .
H39 H 0.7027(19) 0.5664(17) 0.0018(11) 0.031(7) Uiso 1 1 d . . . . .
H34 H 0.7392(18) 1.1208(16) 0.1523(11) 0.028(7) Uiso 1 1 d . . . . .
H36 H 0.488(2) 0.796(2) -0.0722(14) 0.069(11) Uiso 1 1 d . . . . .
H54 H 1.215(2) 0.3730(18) 0.5515(13) 0.045(8) Uiso 1 1 d . . . . .
H59 H 1.052(2) 0.0260(18) 0.1576(13) 0.047(8) Uiso 1 1 d . . . . .
H53 H 0.9734(19) 0.5323(16) 0.6533(11) 0.025(7) Uiso 1 1 d . . . . .
H57 H 0.945(2) 0.1624(17) 0.3041(12) 0.036(7) Uiso 1 1 d . . . . .
H50 H 0.608(2) 0.9327(18) 0.5243(12) 0.044(8) Uiso 1 1 d . . . . .
H58 H 1.231(2) 0.0616(18) 0.1860(12) 0.043(8) Uiso 1 1 d . . . . .
H55 H 1.234(2) 0.5868(18) 0.7066(12) 0.037(8) Uiso 1 1 d . . . . .
H56 H 1.0656(19) 0.2295(16) 0.3655(11) 0.028(7) Uiso 1 1 d . . . . .
H49 H 0.430(2) 0.8750(17) 0.5023(12) 0.040(8) Uiso 1 1 d . . . . .
H48 H 0.569(2) 0.5420(19) 0.0632(12) 0.045(9) Uiso 1 1 d . . . . .
H52 H 0.848(2) 0.6006(18) 0.7094(13) 0.044(9) Uiso 1 1 d . . . . .
H51 H 0.8862(19) 0.6516(18) 0.7656(12) 0.036(8) Uiso 1 1 d . . . . .
H82 H 0.249(3) 0.665(2) 0.3025(14) 0.075(11) Uiso 1 1 d . . . . .
H72 H 0.565(2) 0.9216(18) 0.0395(12) 0.046(8) Uiso 1 1 d . . . . .
H76 H -0.192(2) 0.914(2) 0.2387(14) 0.060(10) Uiso 1 1 d . . . . .
H73 H 0.429(2) 0.9005(18) 0.0430(12) 0.040(8) Uiso 1 1 d . . . . .
H81 H -0.278(3) 0.043(2) -0.0929(15) 0.081(12) Uiso 1 1 d . . . . .
H74 H 0.627(2) 1.0146(19) 0.1061(13) 0.046(9) Uiso 1 1 d . . . . .
H83 H 0.612(3) 1.063(2) 0.3933(15) 0.084(11) Uiso 1 1 d . . . . .
H80 H -0.070(3) 0.311(2) 0.1832(17) 0.082(12) Uiso 1 1 d . . . . .
H78 H 0.636(3) 0.553(2) 0.6573(16) 0.078(12) Uiso 1 1 d . . . . .
H71 H 0.361(2) 0.5385(18) 0.1458(12) 0.042(9) Uiso 1 1 d . . . . .
H75 H 0.6435(19) 1.2485(18) 0.3034(12) 0.040(8) Uiso 1 1 d . . . . .
H70 H 0.465(3) 0.488(2) 0.1264(15) 0.067(12) Uiso 1 1 d . . . . .
H77 H -0.243(3) 0.997(2) 0.3396(14) 0.067(11) Uiso 1 1 d . . . . .
H79 H 0.425(3) 0.251(2) 0.3904(16) 0.094(12) Uiso 1 1 d . . . . .
H106 H 0.355(4) 0.307(3) 0.301(2) 0.141 Uiso 1 1 d . U . . .
H107 H 0.729(4) 0.432(3) 0.080(2) 0.141 Uiso 1 1 d . U . . .
H101 H 0.396(2) 0.6094(19) 0.2490(13) 0.056(9) Uiso 1 1 d . . . . .
H102 H 0.038(3) 0.397(3) 0.0182(19) 0.108(14) Uiso 1 1 d . . . . .
H100 H 0.386(3) 0.741(3) 0.1333(18) 0.107(14) Uiso 1 1 d . . . . .
O32 O 0.41657(13) 0.34852(13) 0.47520(8) 0.0370(5) Uani 1 1 d . . . . .
O31 O 0.50315(14) 0.27099(13) 0.40389(8) 0.0357(5) Uani 1 1 d . . . . .
O27 O 0.62727(14) 0.51665(14) 0.62580(8) 0.0364(5) Uani 1 1 d . . . . .
O26 O 1.31210(13) 0.22154(12) 0.35806(7) 0.0332(5) Uani 1 1 d . . . . .
O30 O 0.90065(13) 0.27825(12) 0.40049(8) 0.0356(5) Uani 1 1 d . . . . .
O28 O 0.80918(14) 0.52145(13) 0.62557(8) 0.0415(5) Uani 1 1 d . . . . .
O25 O 1.08509(13) 0.62744(12) 0.75741(8) 0.0330(5) Uani 1 1 d . . . . .
C3 C 0.80289(18) 0.36219(17) 0.46981(11) 0.0246(6) Uani 1 1 d . . . . .
N5 N 0.90501(17) 0.33503(15) 0.44171(10) 0.0302(5) Uani 1 1 d . . . . .
N3 N 1.2092(2) 0.27997(16) 0.43052(10) 0.0348(6) Uani 1 1 d . . . . .
C5 C 0.71477(19) 0.44152(17) 0.54777(11) 0.0260(6) Uani 1 1 d . . . . .
O29 O 0.99102(13) 0.37016(13) 0.46079(8) 0.0412(5) Uani 1 1 d . . . . .
C14 C 1.0044(2) 0.14198(19) 0.27937(12) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.61016(18) 0.35558(17) 0.47397(11) 0.0253(6) Uani 1 1 d . . . . .
C7 C 0.5002(2) 0.32515(18) 0.45129(11) 0.0287(6) Uani 1 1 d . . . . .
C8 C 1.22041(19) 0.23839(17) 0.37802(11) 0.0256(6) Uani 1 1 d . . . . .
N2 N 1.02959(18) 0.55137(15) 0.67400(9) 0.0292(5) Uani 1 1 d . . . . .
C12 C 1.0670(2) 0.06051(19) 0.19402(13) 0.0359(7) Uani 1 1 d . . . . .
C9 C 1.11133(19) 0.16468(17) 0.29551(11) 0.0257(6) Uani 1 1 d . . . . .
N4 N 1.12666(17) 0.21645(15) 0.34900(9) 0.0281(5) Uani 1 1 d . . . . .
N1 N 0.90515(18) 0.61795(16) 0.73458(11) 0.0301(5) Uani 1 1 d . . . . .
C4 C 0.8100(2) 0.41790(18) 0.51995(11) 0.0269(6) Uani 1 1 d . . . . .
C15 C 1.0094(2) 0.60111(17) 0.72370(11) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.7229(2) 0.49719(18) 0.60346(11) 0.0299(6) Uani 1 1 d . . . . .
C2 C 0.70544(19) 0.32916(18) 0.44638(11) 0.0254(6) Uani 1 1 d . . . . .
C13 C 0.9827(2) 0.0892(2) 0.22910(13) 0.0392(7) Uani 1 1 d . . . . .
C10 C 1.1957(2) 0.13662(18) 0.26005(12) 0.0304(6) Uani 1 1 d . . . . .
C16 C 1.1309(2) 0.51868(17) 0.65379(11) 0.0270(6) Uani 1 1 d . . . . .
C17 C 1.1279(2) 0.45514(19) 0.60658(12) 0.0353(7) Uani 1 1 d . . . . .
C11 C 1.1726(2) 0.08499(19) 0.20912(12) 0.0351(7) Uani 1 1 d . . . . .
C21 C 1.2313(2) 0.5464(2) 0.67709(13) 0.0353(7) Uani 1 1 d . . . . .
C20 C 1.3265(2) 0.5110(2) 0.65355(13) 0.0410(8) Uani 1 1 d . . . . .
C18 C 1.2225(3) 0.4207(2) 0.58351(13) 0.0423(8) Uani 1 1 d . . . . .
C19 C 1.3223(3) 0.4480(2) 0.60668(14) 0.0439(8) Uani 1 1 d . . . . .
O7 O 0.03784(13) 0.43763(12) 0.05716(8) 0.0321(5) Uani 1 1 d . . . . .
O11 O 0.25324(13) 0.56795(12) 0.21851(8) 0.0324(4) Uani 1 1 d . . . . .
O8 O -0.14403(13) 0.44232(12) 0.05335(8) 0.0329(5) Uani 1 1 d . . . . .
O12 O 0.17065(14) 0.65194(12) 0.28835(8) 0.0337(5) Uani 1 1 d . . . . .
O10 O -0.22463(14) 0.68396(13) 0.28319(8) 0.0390(5) Uani 1 1 d . . . . .
O22 O 0.37399(14) 0.66184(13) 0.08395(8) 0.0381(5) Uani 1 1 d . . . . .
O9 O -0.31976(14) 0.61320(14) 0.21495(8) 0.0444(5) Uani 1 1 d . . . . .
N12 N -0.23219(17) 0.63505(15) 0.23863(10) 0.0310(5) Uani 1 1 d . . . . .
C33 C -0.04815(18) 0.51524(16) 0.13444(10) 0.0235(6) Uani 1 1 d . . . . .
C37 C -0.03280(19) 0.61827(18) 0.23886(11) 0.0246(6) Uani 1 1 d . . . . .
C34 C -0.0568(2) 0.46110(17) 0.07750(11) 0.0249(6) Uani 1 1 d . . . . .
C36 C -0.13206(19) 0.60012(17) 0.21174(11) 0.0242(6) Uani 1 1 d . . . . .
C31 C 0.06074(18) 0.58364(17) 0.21344(11) 0.0250(6) Uani 1 1 d . . . . .
C35 C -0.1422(2) 0.54974(17) 0.15958(11) 0.0245(6) Uani 1 1 d . . . . .
C30 C 0.1710(2) 0.60021(17) 0.24030(11) 0.0269(6) Uani 1 1 d . . . . .
C32 C 0.0523(2) 0.53116(17) 0.16150(11) 0.0243(6) Uani 1 1 d . . . . .
N16 N 0.52478(18) 0.58349(17) 0.05385(10) 0.0354(6) Uani 1 1 d . . . . .
C67 C 0.4381(2) 0.5981(2) 0.08800(12) 0.0323(7) Uani 1 1 d . . . . .
C70 C 0.6961(3) 0.6580(2) -0.05955(14) 0.0434(8) Uani 1 1 d . . . . .
C71 C 0.6358(3) 0.7263(2) -0.08127(13) 0.0432(8) Uani 1 1 d . . . . .
C72 C 0.5368(3) 0.7487(2) -0.05746(13) 0.0432(8) Uani 1 1 d . . . . .
C73 C 0.4968(2) 0.7038(2) -0.01277(13) 0.0379(7) Uani 1 1 d . . . . .
C69 C 0.5588(2) 0.63493(19) 0.00919(12) 0.0318(7) Uani 1 1 d . . . . .
N17 N 0.4274(2) 0.5381(2) 0.12777(11) 0.0449(7) Uani 1 1 d . . . . .
C68 C 0.6593(2) 0.6129(2) -0.01486(13) 0.0376(7) Uani 1 1 d . . . . .
O5 O 0.10751(13) 0.27880(12) 0.15140(7) 0.0316(4) Uani 1 1 d . . . . .
O3 O -0.20389(15) 0.05650(13) -0.08001(8) 0.0369(5) Uani 1 1 d . . . . .
O6 O -0.07546(13) 0.28065(13) 0.14782(8) 0.0354(5) Uani 1 1 d . . . . .
O2 O 0.19040(13) 0.02278(12) -0.07184(8) 0.0359(5) Uani 1 1 d . . . . .
O4 O -0.28681(14) 0.14428(13) -0.01217(9) 0.0424(5) Uani 1 1 d . . . . .
C23 C 0.01247(18) 0.19981(16) 0.07261(11) 0.0240(6) Uani 1 1 d . . . . .
O1 O 0.28537(14) 0.09432(13) -0.00389(8) 0.0426(5) Uani 1 1 d . . . . .
C24 C 0.1064(2) 0.16386(17) 0.04883(11) 0.0246(6) Uani 1 1 d . . . . .
C25 C 0.09815(18) 0.11235(16) -0.00306(11) 0.0234(6) Uani 1 1 d . . . . .
N15 N 0.19814(17) 0.07414(14) -0.02823(10) 0.0297(5) Uani 1 1 d . . . . .
C22 C 0.0208(2) 0.25697(17) 0.12827(11) 0.0262(6) Uani 1 1 d . . . . .
C27 C -0.0872(2) 0.18345(17) 0.04481(11) 0.0247(6) Uani 1 1 d . . . . .
C26 C -0.00089(19) 0.09480(17) -0.03141(11) 0.0250(6) Uani 1 1 d . . . . .
C28 C -0.09421(18) 0.13027(16) -0.00683(11) 0.0243(6) Uani 1 1 d . . . . .
C29 C -0.2046(2) 0.11211(18) -0.03351(11) 0.0284(6) Uani 1 1 d . . . . .
O20 O 0.21366(14) 0.77215(13) 0.17295(8) 0.0382(5) Uani 1 1 d . . . . .
N10 N -0.09909(18) 1.07313(15) 0.44332(10) 0.0321(6) Uani 1 1 d . . . . .
O21 O 0.38742(13) 1.00130(12) 0.12228(8) 0.0367(5) Uani 1 1 d . . . . .
O18 O 0.61388(13) 0.96351(12) 0.30826(8) 0.0354(5) Uani 1 1 d . . . . .
O19 O 0.39403(14) 0.78743(14) 0.16527(9) 0.0416(5) Uani 1 1 d . . . . .
O13 O -0.27958(13) 1.09707(12) 0.42319(8) 0.0355(5) Uani 1 1 d . . . . .
O17 O 0.53187(14) 1.04385(13) 0.38024(8) 0.0353(5) Uani 1 1 d . . . . .
N8 N 0.57046(18) 1.03205(16) 0.12206(10) 0.0324(6) Uani 1 1 d . . . . .
O15 O 0.13625(14) 1.02235(13) 0.39671(9) 0.0414(5) Uani 1 1 d . . . . .
O16 O 0.04232(14) 0.93715(13) 0.33443(9) 0.0429(5) Uani 1 1 d . . . . .
O14 O -0.04754(13) 0.65876(12) 0.03498(7) 0.0304(4) Uani 1 1 d . . . . .
C55 C 0.31215(18) 0.86341(16) 0.24444(11) 0.0251(6) Uani 1 1 d . . . . .
N18 N 0.12909(17) 0.96904(15) 0.35385(10) 0.0325(5) Uani 1 1 d . . . . .
N13 N 0.00313(17) 0.74382(15) 0.11587(9) 0.0280(5) Uani 1 1 d . . . . .
C57 C 0.4125(2) 0.89713(17) 0.26452(11) 0.0267(6) Uani 1 1 d . . . . .
C56 C 0.3014(2) 0.80320(17) 0.19052(11) 0.0282(6) Uani 1 1 d . . . . .
C53 C 0.22950(19) 0.94283(17) 0.32386(11) 0.0253(6) Uani 1 1 d . . . . .
C58 C 0.42189(19) 0.95386(17) 0.31450(11) 0.0260(6) Uani 1 1 d . . . . .
C60 C 0.4787(2) 0.98735(18) 0.10098(12) 0.0303(6) Uani 1 1 d . . . . .
C59 C 0.3283(2) 0.97807(18) 0.34458(12) 0.0274(6) Uani 1 1 d . . . . .
C54 C 0.2189(2) 0.88562(17) 0.27450(11) 0.0269(6) Uani 1 1 d . . . . .
C50 C -0.1700(2) 1.15839(19) 0.52913(12) 0.0305(6) Uani 1 1 d . . . . .
C40 C -0.0967(2) 0.83787(19) 0.18299(12) 0.0360(7) Uani 1 1 d . . . . .
C46 C -0.08472(19) 1.12981(17) 0.49431(11) 0.0275(6) Uani 1 1 d . . . . .
C39 C -0.0983(2) 0.77794(17) 0.13425(11) 0.0270(6) Uani 1 1 d . . . . .
N11 N -0.1796(2) 1.00924(18) 0.36109(11) 0.0432(7) Uani 1 1 d . . . . .
C47 C 0.0204(2) 1.15613(19) 0.50987(12) 0.0331(7) Uani 1 1 d . . . . .
C49 C -0.0443(2) 1.2414(2) 0.59350(12) 0.0356(7) Uani 1 1 d . . . . .
C51 C -0.1488(2) 1.21407(19) 0.57825(12) 0.0336(7) Uani 1 1 d . . . . .
N9 N 0.4937(2) 0.92755(17) 0.05611(11) 0.0407(7) Uani 1 1 d . . . . .
C52 C 0.5323(2) 0.98714(18) 0.33384(11) 0.0290(6) Uani 1 1 d . . . . .
N14 N 0.13053(18) 0.66504(17) 0.06232(11) 0.0316(6) Uani 1 1 d . . . . .
C43 C -0.1980(2) 0.75499(19) 0.10745(12) 0.0312(7) Uani 1 1 d . . . . .
C38 C 0.0266(2) 0.68758(17) 0.06905(11) 0.0255(6) Uani 1 1 d . . . . .
C48 C 0.0407(2) 1.2113(2) 0.55928(13) 0.0404(8) Uani 1 1 d . . . . .
C45 C -0.1911(2) 1.06163(18) 0.40966(12) 0.0314(7) Uani 1 1 d . . . . .
C61 C 0.58385(19) 1.09163(17) 0.17157(11) 0.0285(6) Uani 1 1 d . . . . .
C66 C 0.5039(2) 1.10842(19) 0.21207(12) 0.0321(7) Uani 1 1 d . . . . .
C44 C -0.2928(2) 0.7907(2) 0.13012(13) 0.0391(7) Uani 1 1 d . . . . .
C65 C 0.5269(2) 1.1656(2) 0.26022(13) 0.0362(7) Uani 1 1 d . . . . .
C64 C 0.6264(2) 1.2079(2) 0.26909(13) 0.0382(7) Uani 1 1 d . . . . .
C41 C -0.1927(3) 0.8733(2) 0.20483(14) 0.0452(8) Uani 1 1 d . . . . .
C42 C -0.2911(3) 0.8501(2) 0.17852(14) 0.0459(8) Uani 1 1 d . . . . .
C62 C 0.6847(2) 1.1344(2) 0.18027(13) 0.0386(7) Uani 1 1 d . . . . .
C63 C 0.7058(2) 1.1919(2) 0.22866(13) 0.0424(8) Uani 1 1 d . . . . .
O23 O 0.35453(13) 0.69539(12) 0.33681(7) 0.0326(5) Uani 1 1 d . . . . .
N7 N 0.4613(2) 0.63378(18) 0.26702(11) 0.0425(7) Uani 1 1 d . . . . .
N6 N 0.53739(17) 0.72613(15) 0.33970(9) 0.0311(6) Uani 1 1 d . . . . .
C74 C 0.44657(19) 0.68578(18) 0.31573(11) 0.0287(6) Uani 1 1 d . . . . .
C80 C 0.6543(2) 0.81512(19) 0.40460(12) 0.0342(7) Uani 1 1 d . . . . .
C75 C 0.55024(19) 0.78218(17) 0.39157(11) 0.0268(6) Uani 1 1 d . . . . .
C76 C 0.4659(2) 0.80466(19) 0.42795(12) 0.0321(7) Uani 1 1 d . . . . .
C77 C 0.4874(2) 0.8604(2) 0.47748(13) 0.0381(7) Uani 1 1 d . . . . .
C78 C 0.5914(2) 0.8932(2) 0.49023(12) 0.0362(7) Uani 1 1 d . . . . .
C79 C 0.6746(2) 0.8705(2) 0.45397(13) 0.0381(7) Uani 1 1 d . . . . .
O100 O 0.34520(16) 0.36357(14) 0.28758(8) 0.0419(5) Uani 1 1 d . . . . .
C101 C 0.3695(3) 0.3577(2) 0.22861(13) 0.0623(10) Uani 1 1 d . . . . .
H10A H 0.3620 0.4166 0.2143 0.093 Uiso 1 1 calc R U . . .
H10B H 0.3200 0.3156 0.2082 0.093 Uiso 1 1 calc R U . . .
H10C H 0.4430 0.3369 0.2235 0.093 Uiso 1 1 calc R U . . .
O101 O 0.64884(16) 0.43568(14) 0.09920(10) 0.0499(6) Uani 1 1 d . . . . .
C100 C 0.6569(3) 0.3784(3) 0.14542(17) 0.0686(11) Uani 1 1 d . . . . .
H10D H 0.7213 0.3943 0.1681 0.103 Uiso 1 1 calc R U . . .
H10E H 0.6611 0.3159 0.1306 0.103 Uiso 1 1 calc R U . . .
H10F H 0.5937 0.3864 0.1687 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C200 C1 1.384(3) . ?
C200 C5 1.385(3) . ?
O32 C7 1.217(3) . ?
O31 C7 1.320(3) . ?
O27 C6 1.318(3) . ?
O26 C8 1.246(3) . ?
O30 N5 1.229(3) . ?
O28 C6 1.209(3) . ?
O25 C15 1.248(3) . ?
C3 C2 1.375(3) . ?
C3 C4 1.383(3) . ?
C3 N5 1.470(3) . ?
N5 O29 1.232(3) . ?
N3 C8 1.344(3) . ?
C5 C4 1.382(3) . ?
C5 C6 1.490(3) . ?
C14 C13 1.382(4) . ?
C14 C9 1.389(3) . ?
C1 C2 1.390(3) . ?
C1 C7 1.493(3) . ?
C8 N4 1.349(3) . ?
N2 C15 1.357(3) . ?
N2 C16 1.413(3) . ?
C12 C11 1.373(4) . ?
C12 C13 1.383(4) . ?
C9 C10 1.387(3) . ?
C9 N4 1.427(3) . ?
N1 C15 1.329(3) . ?
C10 C11 1.390(4) . ?
C16 C21 1.383(4) . ?
C16 C17 1.394(4) . ?
C17 C18 1.374(4) . ?
C21 C20 1.388(4) . ?
C20 C19 1.384(4) . ?
C18 C19 1.373(4) . ?
O7 C34 1.302(3) . ?
O11 C30 1.222(3) . ?
O8 C34 1.220(3) . ?
O12 C30 1.312(3) . ?
O10 N12 1.225(3) . ?
O22 C67 1.235(3) . ?
O9 N12 1.228(3) . ?
N12 C36 1.469(3) . ?
C33 C32 1.385(3) . ?
C33 C35 1.387(3) . ?
C33 C34 1.505(3) . ?
C37 C36 1.377(3) . ?
C37 C31 1.385(3) . ?
C36 C35 1.385(3) . ?
C31 C32 1.395(3) . ?
C31 C30 1.490(3) . ?
N16 C67 1.353(3) . ?
N16 C69 1.410(3) . ?
C67 N17 1.344(4) . ?
C70 C68 1.369(4) . ?
C70 C71 1.376(4) . ?
C71 C72 1.378(4) . ?
C72 C73 1.381(4) . ?
C73 C69 1.395(4) . ?
C69 C68 1.395(4) . ?
O5 C22 1.214(3) . ?
O3 C29 1.314(3) . ?
O6 C22 1.314(3) . ?
O2 N15 1.227(3) . ?
O4 C29 1.216(3) . ?
C23 C24 1.381(3) . ?
C23 C27 1.384(3) . ?
C23 C22 1.500(3) . ?
O1 N15 1.226(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.386(3) . ?
C25 N15 1.468(3) . ?
C27 C28 1.393(3) . ?
C26 C28 1.379(3) . ?
C28 C29 1.494(3) . ?
O20 C56 1.218(3) . ?
N10 C45 1.366(3) . ?
N10 C46 1.413(3) . ?
O21 C60 1.247(3) . ?
O18 C52 1.216(3) . ?
O19 C56 1.306(3) . ?
O13 C45 1.243(3) . ?
O17 C52 1.321(3) . ?
N8 C60 1.365(3) . ?
N8 C61 1.408(3) . ?
O15 N18 1.229(3) . ?
O16 N18 1.225(3) . ?
O14 C38 1.249(3) . ?
C55 C57 1.383(3) . ?
C55 C54 1.384(3) . ?
C55 C56 1.492(3) . ?
N18 C53 1.470(3) . ?
N13 C38 1.361(3) . ?
N13 C39 1.407(3) . ?
C57 C58 1.390(3) . ?
C53 C59 1.379(3) . ?
C53 C54 1.383(3) . ?
C58 C59 1.394(3) . ?
C58 C52 1.487(3) . ?
C60 N9 1.337(3) . ?
C50 C51 1.382(4) . ?
C50 C46 1.388(4) . ?
C40 C41 1.382(4) . ?
C40 C39 1.390(4) . ?
C46 C47 1.377(3) . ?
C39 C43 1.391(4) . ?
N11 C45 1.338(3) . ?
C47 C48 1.382(4) . ?
C49 C51 1.373(4) . ?
C49 C48 1.383(4) . ?
N14 C38 1.328(3) . ?
C43 C44 1.378(4) . ?
C61 C62 1.389(3) . ?
C61 C66 1.391(4) . ?
C66 C65 1.380(4) . ?
C44 C42 1.379(4) . ?
C65 C64 1.372(4) . ?
C64 C63 1.382(4) . ?
C41 C42 1.374(4) . ?
C62 C63 1.383(4) . ?
O23 C74 1.246(3) . ?
N7 C74 1.343(3) . ?
N6 C74 1.351(3) . ?
N6 C75 1.423(3) . ?
C80 C79 1.383(4) . ?
C80 C75 1.382(3) . ?
C75 C76 1.381(3) . ?
C76 C77 1.391(4) . ?
C77 C78 1.379(4) . ?
C78 C79 1.368(4) . ?
O100 C101 1.420(3) . ?
O101 C100 1.429(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
C1 C200 C5 120.9(2) . . ?
C2 C3 C4 123.0(2) . . ?
C2 C3 N5 119.0(2) . . ?
C4 C3 N5 118.0(2) . . ?
O30 N5 O29 123.1(2) . . ?
O30 N5 C3 118.6(2) . . ?
O29 N5 C3 118.3(2) . . ?
C4 C5 C200 119.6(2) . . ?
C4 C5 C6 118.5(2) . . ?
C200 C5 C6 121.9(2) . . ?
C13 C14 C9 120.1(3) . . ?
C200 C1 C2 120.1(2) . . ?
C200 C1 C7 117.9(2) . . ?
C2 C1 C7 122.0(2) . . ?
O32 C7 O31 124.1(2) . . ?
O32 C7 C1 122.1(2) . . ?
O31 C7 C1 113.7(2) . . ?
O26 C8 N3 121.4(2) . . ?
O26 C8 N4 122.9(2) . . ?
N3 C8 N4 115.7(2) . . ?
C15 N2 C16 128.1(2) . . ?
C11 C12 C13 119.8(3) . . ?
C10 C9 C14 119.6(2) . . ?
C10 C9 N4 124.0(2) . . ?
C14 C9 N4 116.4(2) . . ?
C8 N4 C9 128.9(2) . . ?
C5 C4 C3 118.6(2) . . ?
O25 C15 N1 122.5(2) . . ?
O25 C15 N2 121.2(2) . . ?
N1 C15 N2 116.2(2) . . ?
O28 C6 O27 123.9(2) . . ?
O28 C6 C5 122.7(2) . . ?
O27 C6 C5 113.4(2) . . ?
C3 C2 C1 117.8(2) . . ?
C14 C13 C12 120.3(3) . . ?
C9 C10 C11 119.7(2) . . ?
C21 C16 C17 118.7(2) . . ?
C21 C16 N2 124.5(2) . . ?
C17 C16 N2 116.8(2) . . ?
C18 C17 C16 120.8(3) . . ?
C12 C11 C10 120.6(3) . . ?
C16 C21 C20 120.1(3) . . ?
C19 C20 C21 120.7(3) . . ?
C19 C18 C17 120.6(3) . . ?
C18 C19 C20 119.2(3) . . ?
O10 N12 O9 123.3(2) . . ?
O10 N12 C36 118.9(2) . . ?
O9 N12 C36 117.7(2) . . ?
C32 C33 C35 120.1(2) . . ?
C32 C33 C34 120.7(2) . . ?
C35 C33 C34 119.2(2) . . ?
C36 C37 C31 118.8(2) . . ?
O8 C34 O7 124.3(2) . . ?
O8 C34 C33 122.8(2) . . ?
O7 C34 C33 112.9(2) . . ?
C37 C36 C35 122.7(2) . . ?
C37 C36 N12 119.4(2) . . ?
C35 C36 N12 117.9(2) . . ?
C37 C31 C32 119.6(2) . . ?
C37 C31 C30 121.8(2) . . ?
C32 C31 C30 118.6(2) . . ?
C36 C35 C33 118.2(2) . . ?
O11 C30 O12 124.1(2) . . ?
O11 C30 C31 121.8(2) . . ?
O12 C30 C31 114.1(2) . . ?
C33 C32 C31 120.7(2) . . ?
C67 N16 C69 128.2(3) . . ?
O22 C67 N17 121.9(3) . . ?
O22 C67 N16 123.4(3) . . ?
N17 C67 N16 114.6(3) . . ?
C68 C70 C71 121.0(3) . . ?
C70 C71 C72 118.9(3) . . ?
C71 C72 C73 121.6(3) . . ?
C72 C73 C69 119.2(3) . . ?
C73 C69 C68 119.0(3) . . ?
C73 C69 N16 123.9(2) . . ?
C68 C69 N16 117.1(3) . . ?
C70 C68 C69 120.4(3) . . ?
C24 C23 C27 119.9(2) . . ?
C24 C23 C22 119.0(2) . . ?
C27 C23 C22 121.1(2) . . ?
C23 C24 C25 118.6(2) . . ?
C26 C25 C24 122.4(2) . . ?
C26 C25 N15 119.1(2) . . ?
C24 C25 N15 118.5(2) . . ?
O1 N15 O2 123.3(2) . . ?
O1 N15 C25 117.9(2) . . ?
O2 N15 C25 118.7(2) . . ?
O5 C22 O6 125.0(2) . . ?
O5 C22 C23 122.8(2) . . ?
O6 C22 C23 112.2(2) . . ?
C23 C27 C28 120.8(2) . . ?
C28 C26 C25 118.4(2) . . ?
C26 C28 C27 120.0(2) . . ?
C26 C28 C29 121.9(2) . . ?
C27 C28 C29 118.2(2) . . ?
O4 C29 O3 124.3(2) . . ?
O4 C29 C28 121.8(2) . . ?
O3 C29 C28 113.8(2) . . ?
C45 N10 C46 127.8(2) . . ?
C60 N8 C61 129.0(2) . . ?
C57 C55 C54 119.9(2) . . ?
C57 C55 C56 121.5(2) . . ?
C54 C55 C56 118.6(2) . . ?
O16 N18 O15 123.4(2) . . ?
O16 N18 C53 118.1(2) . . ?
O15 N18 C53 118.5(2) . . ?
C38 N13 C39 129.4(2) . . ?
C55 C57 C58 121.3(2) . . ?
O20 C56 O19 124.5(2) . . ?
O20 C56 C55 122.0(2) . . ?
O19 C56 C55 113.5(2) . . ?
C59 C53 C54 123.2(2) . . ?
C59 C53 N18 119.4(2) . . ?
C54 C53 N18 117.4(2) . . ?
C57 C58 C59 119.3(2) . . ?
C57 C58 C52 118.4(2) . . ?
C59 C58 C52 122.2(2) . . ?
O21 C60 N9 122.5(2) . . ?
O21 C60 N8 122.2(2) . . ?
N9 C60 N8 115.3(2) . . ?
C53 C59 C58 118.2(3) . . ?
C53 C54 C55 118.1(2) . . ?
C51 C50 C46 119.8(2) . . ?
C41 C40 C39 120.6(3) . . ?
C47 C46 C50 119.3(2) . . ?
C47 C46 N10 117.2(2) . . ?
C50 C46 N10 123.5(2) . . ?
C40 C39 C43 118.9(2) . . ?
C40 C39 N13 116.5(2) . . ?
C43 C39 N13 124.5(2) . . ?
C46 C47 C48 120.4(2) . . ?
C51 C49 C48 119.0(3) . . ?
C49 C51 C50 121.1(3) . . ?
O18 C52 O17 124.5(2) . . ?
O18 C52 C58 121.8(2) . . ?
O17 C52 C58 113.7(2) . . ?
C44 C43 C39 119.6(3) . . ?
O14 C38 N14 122.7(2) . . ?
O14 C38 N13 120.5(2) . . ?
N14 C38 N13 116.7(2) . . ?
C47 C48 C49 120.5(3) . . ?
O13 C45 N11 122.1(2) . . ?
O13 C45 N10 122.5(2) . . ?
N11 C45 N10 115.4(2) . . ?
C62 C61 C66 118.8(3) . . ?
C62 C61 N8 116.9(2) . . ?
C66 C61 N8 124.2(2) . . ?
C65 C66 C61 119.6(3) . . ?
C43 C44 C42 121.5(3) . . ?
C64 C65 C66 121.9(3) . . ?
C65 C64 C63 118.7(3) . . ?
C42 C41 C40 120.4(3) . . ?
C41 C42 C44 119.0(3) . . ?
C63 C62 C61 120.6(3) . . ?
C64 C63 C62 120.4(3) . . ?
C74 N6 C75 129.6(2) . . ?
O23 C74 N7 121.3(2) . . ?
O23 C74 N6 123.0(2) . . ?
N7 C74 N6 115.6(2) . . ?
C79 C80 C75 120.3(3) . . ?
C76 C75 C80 120.0(3) . . ?
C76 C75 N6 123.8(2) . . ?
C80 C75 N6 116.2(2) . . ?
C75 C76 C77 119.1(2) . . ?
C78 C77 C76 120.7(3) . . ?
C79 C78 C77 119.8(3) . . ?
C78 C79 C80 120.1(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
C35 H8 O101 1.01(2) 2.38(2) 3.290(3) 149.1(17) 1_455
C50 H10 O13 0.93(2) 2.34(2) 2.884(3) 117.1(17) .
N11 H14 O16 0.86(2) 2.13(3) 2.986(3) 171(2) .
N6 H16 O10 0.88(3) 2.40(3) 3.273(3) 177(2) 1_655
N10 H12 O15 0.87(2) 2.33(2) 3.180(3) 165(2) .
C76 H19 O23 0.95(2) 2.27(3) 2.891(3) 122.3(19) .
C66 H20 O21 0.94(2) 2.30(3) 2.883(3) 119.6(19) .
N7 H17 O9 0.88(3) 2.10(3) 2.981(3) 176(2) 1_655
N13 H28 O20 0.88(2) 2.04(2) 2.896(3) 162(2) .
C43 H29 O14 0.97(3) 2.22(2) 2.845(3) 120.6(18) .
N14 H27 O22 0.89(3) 2.35(3) 3.018(3) 132(2) .
N14 H27 O20 0.89(3) 2.35(3) 3.085(3) 140(2) .
N14 H26 O8 0.88(3) 2.20(3) 3.044(3) 161(2) 2_565
C10 H43 O26 0.94(2) 2.30(2) 2.881(3) 119.1(18) .
N3 H41 O29 0.90(2) 2.18(3) 3.065(3) 169(2) .
N3 H42 O32 0.96(3) 1.93(3) 2.877(3) 170(2) 1_655
C73 H35 O22 0.95(2) 2.23(3) 2.859(4) 123(2) .
N2 H53 O28 0.87(2) 2.10(2) 2.927(3) 158(2) .
C21 H55 O25 0.88(3) 2.26(3) 2.831(3) 122(2) .
N4 H56 O30 0.87(2) 2.30(2) 3.157(3) 172(2) .
N16 H48 O101 0.85(3) 2.08(3) 2.918(3) 167(3) .
N1 H52 O28 0.93(3) 2.25(3) 3.042(3) 142(2) .
N1 H52 O100 0.93(3) 2.42(3) 3.119(3) 131(2) 2_666
N1 H51 O5 0.88(3) 2.13(3) 2.984(3) 161(2) 2_666
O12 H82 O23 1.02(3) 1.56(3) 2.559(2) 166(3) .
N9 H72 O1 0.96(3) 2.04(3) 3.006(3) 179(2) 2_665
N9 H73 O4 0.92(3) 1.97(3) 2.882(3) 174(2) 2_565
O3 H81 O21 0.96(3) 1.61(4) 2.555(2) 165(3) 2_565
N8 H74 O2 0.83(3) 2.44(3) 3.265(3) 171(3) 2_665
O17 H83 O13 1.06(3) 1.55(3) 2.595(2) 169(3) 1_655
O6 H80 O25 0.92(4) 1.62(4) 2.520(3) 168(3) 2_666
O27 H78 O100 0.88(4) 1.72(4) 2.603(3) 172(3) 2_666
N17 H71 O11 0.92(3) 2.20(3) 3.058(3) 154(2) .
N17 H70 O101 0.87(3) 2.46(3) 3.171(4) 139(3) .
N11 H77 O18 0.93(3) 1.93(3) 2.850(3) 169(3) 1_455
O31 H79 O26 1.04(4) 1.60(4) 2.632(2) 170(3) 1_455
O100 H106 O26 0.92(5) 1.99(5) 2.801(3) 146(4) 1_455
O101 H107 O8 1.09(4) 1.70(4) 2.783(3) 172(4) 1_655
N7 H101 O11 0.95(3) 1.96(3) 2.902(3) 173(3) .
O7 H102 O14 1.05(4) 1.45(4) 2.500(2) 175(3) 2_565
O19 H100 O22 0.98(4) 1.58(4) 2.561(3) 177(4) .
C101 H10A O11 0.96 2.60 3.439(4) 146.3 .

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method methanol
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM2
_database_code_depnum_ccdc_archive 'CCDC 1471783'
_audit_update_record             
;
2016-06-09 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_DIFMX01_IM2                 
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: It is not possible to fully resolve the disordered solvent in the
channels of this material.
;
_vrf_PLAT430_IM2                 
;
PROBLEM: Short Inter D...A Contact O17 .. O18 .. 2.17 Ang. 
RESPONSE: O17 is a disordered solvent molecule with a half occupancy.
;



_vrf_PLAT097_IM2                 
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.12 eA-3
RESPONSE: It is not possible to fully resolve the disordered solvent in the
channels of this material. 
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'tris(n-phenylurea) bis(5-nitroisophthalic acid) monohydrate ethanol solvate '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'3(C7 H8 N2 O1), 2(C8 H5 N1 O6), C2 H6 O1, H2 O1'
_chemical_formula_sum            'C39 H42 N8 O17'
_chemical_formula_weight         894.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0067 0.0031 '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 0.0123 0.0063 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0206 0.0115 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9335(3)
_cell_length_b                   12.4902(7)
_cell_length_c                   25.4854(13)
_cell_angle_alpha                89.062(5)
_cell_angle_beta                 83.694(4)
_cell_angle_gamma                74.923(3)
_cell_volume                     2118.02(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3788
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      35.63
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2014/1 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_T_max  0.7472

_exptl_special_details           
;
 ?
;

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.9538
_diffrn_reflns_number            20333
_diffrn_reflns_av_unetI/netI     0.1490
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         34.590
_diffrn_reflns_theta_full        34.909
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             7477
_reflns_number_gt                3492
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

Hydroxyl hydrogen atoms on the 5-nitroisophthalic acid molecules were fixed in riding
positions using HFIX 83.

The primary amine N--H groups of the n-phenylurea molecules were fixed in riding 
positions using HFIX 93.

The aromatic C--H groups were all fixed in riding positions using HFIX 43.

It was not possible to anisotropically refine the heavy atoms in the ethanol solvent 
and water molecules. Nor was it possible to fully resolve solvent molecule hydrogen atoms. 

Residual electron density in the structure:
_refine_diff_density_max 1.12 
This peak is next to an isotropically refined oxygen atom of a water molecule whose 
structure, including hydrogen atoms, could not be fully resolved. 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1899P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7477
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1972
_refine_ls_R_factor_gt           0.1019
_refine_ls_wR_factor_ref         0.3331
_refine_ls_wR_factor_gt          0.2761
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.0611(9) 0.1077(5) 0.0878(2) 0.0232(14) Uani 1 1 d . . . . .
C10 C 0.0617(9) -0.0018(5) 0.1122(2) 0.0219(14) Uani 1 1 d . . . . .
C11 C 0.1013(9) -0.0965(5) 0.0812(2) 0.0225(14) Uani 1 1 d . . . . .
C12 C 0.1110(9) -0.1962(5) 0.1063(2) 0.0251(15) Uani 1 1 d . . . . .
C13 C 0.0825(9) -0.2055(5) 0.1613(3) 0.0288(16) Uani 1 1 d . . . . .
C14 C 0.0465(9) -0.1103(5) 0.1915(2) 0.0251(15) Uani 1 1 d . . . . .
C15 C 0.0347(9) -0.0088(5) 0.1664(2) 0.0256(15) Uani 1 1 d . . . . .
C16 C 0.0210(10) -0.1178(6) 0.2500(3) 0.0336(17) Uani 1 1 d . . . . .
N2 N 0.1562(8) -0.2992(5) 0.0740(2) 0.0337(14) Uani 1 1 d . . . . .
O7 O 0.0286(8) -0.2070(4) 0.27218(18) 0.0427(13) Uani 1 1 d . . . . .
O8 O -0.0053(8) -0.0245(4) 0.27505(18) 0.0420(13) Uani 1 1 d . . . . .
O9 O 0.0332(7) 0.1921(3) 0.11466(17) 0.0313(11) Uani 1 1 d . . . . .
O10 O 0.1013(6) 0.1031(3) 0.03608(16) 0.0291(11) Uani 1 1 d . . . . .
O11 O 0.2288(8) -0.2977(4) 0.0283(2) 0.0434(13) Uani 1 1 d . . . . .
O12 O 0.1189(8) -0.3823(4) 0.0955(2) 0.0448(13) Uani 1 1 d . . . . .
C31 C 0.8005(9) 0.6391(5) -0.0137(3) 0.0257(15) Uani 1 1 d . . . . .
C32 C 0.6628(9) 0.5549(5) 0.0685(2) 0.0264(15) Uani 1 1 d . . . . .
C33 C 0.6017(11) 0.4630(5) 0.0853(3) 0.0352(17) Uani 1 1 d . . . . .
C34 C 0.5229(11) 0.4551(6) 0.1369(3) 0.0364(18) Uani 1 1 d . . . . .
C35 C 0.5034(10) 0.5407(5) 0.1723(3) 0.0320(17) Uani 1 1 d . . . . .
C36 C 0.5660(10) 0.6331(5) 0.1559(3) 0.0301(16) Uani 1 1 d . . . . .
C37 C 0.6441(10) 0.6410(5) 0.1033(2) 0.0293(16) Uani 1 1 d . . . . .
N7 N 0.7389(8) 0.5566(4) 0.0141(2) 0.0275(13) Uani 1 1 d . . . . .
N8 N 0.8569(8) 0.6183(4) -0.0648(2) 0.0322(14) Uani 1 1 d . . . . .
O15 O 0.8002(7) 0.7281(3) 0.00767(16) 0.0310(11) Uani 1 1 d . . . . .
C1 C 0.2509(11) 0.5906(6) 0.5176(3) 0.0332(17) Uani 1 1 d . . . . .
C2 C 0.3019(9) 0.5711(5) 0.5727(2) 0.0269(15) Uani 1 1 d . . . . .
C3 C 0.3406(9) 0.4659(5) 0.5945(2) 0.0266(15) Uani 1 1 d . . . . .
C4 C 0.3861(9) 0.4483(5) 0.6454(2) 0.0239(14) Uani 1 1 d . . . . .
C5 C 0.3951(8) 0.5369(5) 0.6768(2) 0.0228(14) Uani 1 1 d . . . . .
C6 C 0.3596(9) 0.6413(5) 0.6544(2) 0.0275(15) Uani 1 1 d . . . . .
C7 C 0.3138(10) 0.6603(5) 0.6037(3) 0.0295(16) Uani 1 1 d . . . . .
C8 C 0.4279(10) 0.3320(5) 0.6666(3) 0.0268(15) Uani 1 1 d . . . . .
N1 N 0.3707(8) 0.7351(5) 0.6866(2) 0.0329(14) Uani 1 1 d . . . . .
O1 O 0.4711(7) 0.3244(4) 0.71489(16) 0.0365(12) Uani 1 1 d . . . . .
O2 O 0.4150(7) 0.2542(4) 0.64006(17) 0.0375(12) Uani 1 1 d . . . . .
O3 O 0.3918(7) 0.7224(4) 0.73343(19) 0.0374(12) Uani 1 1 d . . . . .
O4 O 0.3646(9) 0.8235(4) 0.6637(2) 0.0564(16) Uani 1 1 d . . . . .
O5 O 0.2222(9) 0.6810(4) 0.49707(19) 0.0513(15) Uani 1 1 d . . . . .
O6 O 0.2456(7) 0.4991(4) 0.49375(17) 0.0378(12) Uani 1 1 d . . . . .
C17 C 0.1196(10) 0.5862(6) 0.3695(3) 0.0289(16) Uani 1 1 d . . . . .
C18 C 0.0867(9) 0.4740(5) 0.2927(2) 0.0276(15) Uani 1 1 d . . . . .
C19 C 0.0254(11) 0.4868(6) 0.2422(3) 0.0385(18) Uani 1 1 d . . . . .
C20 C 0.0183(11) 0.3959(7) 0.2135(3) 0.048(2) Uani 1 1 d . . . . .
C21 C 0.0749(12) 0.2906(7) 0.2343(3) 0.047(2) Uani 1 1 d . . . . .
C22 C 0.1319(10) 0.2776(6) 0.2839(3) 0.0403(18) Uani 1 1 d . . . . .
C23 C 0.1402(10) 0.3700(6) 0.3135(3) 0.0346(17) Uani 1 1 d . . . . .
C24 C 0.5122(10) -0.0486(5) 0.2591(3) 0.0301(16) Uani 1 1 d . . . . .
C25 C 0.5413(9) 0.0426(5) 0.1709(2) 0.0234(14) Uani 1 1 d . . . . .
C26 C 0.5426(10) 0.1436(5) 0.1492(3) 0.0310(16) Uani 1 1 d . . . . .
C27 C 0.5596(10) 0.1552(5) 0.0950(3) 0.0329(17) Uani 1 1 d . . . . .
C28 C 0.5805(10) 0.0651(5) 0.0619(3) 0.0300(16) Uani 1 1 d . . . . .
C29 C 0.5797(9) -0.0371(5) 0.0842(2) 0.0272(15) Uani 1 1 d . . . . .
C30 C 0.5616(9) -0.0493(5) 0.1381(2) 0.0273(15) Uani 1 1 d . . . . .
N3 N 0.0884(8) 0.5729(4) 0.3187(2) 0.0316(14) Uani 1 1 d . . . . .
N4 N 0.1124(9) 0.6900(4) 0.3837(2) 0.0390(15) Uani 1 1 d . . . . .
N5 N 0.5305(8) 0.0363(4) 0.2270(2) 0.0304(13) Uani 1 1 d . . . . .
N6 N 0.5153(9) -0.0329(5) 0.3108(2) 0.0388(15) Uani 1 1 d . . . . .
O13 O 0.1565(7) 0.5065(4) 0.40052(16) 0.0332(11) Uani 1 1 d . . . . .
O14 O 0.4860(7) -0.1368(3) 0.24176(17) 0.0336(12) Uani 1 1 d . . . . .
C38 C 1.024(3) 1.0120(14) 0.4019(7) 0.147(6) Uiso 1 1 d . . . . .
O16 O 0.9418(11) 0.9513(6) 0.3771(3) 0.090(2) Uiso 1 1 d . . . . .
C39 C 1.187(3) 0.9375(18) 0.4381(8) 0.205(8) Uiso 1 1 d . . . . .
O17 O 0.6738(19) 0.8648(10) 0.4406(5) 0.076(4) Uiso 0.5 1 d . . P . .
O18 O 0.666(3) 0.7974(17) 0.5196(8) 0.147(7) Uiso 0.5 1 d . . P . .
H7 H 0.1207 -0.0931 0.0445 0.027 Uiso 1 1 calc R U . . .
H8 H 0.0877 -0.2738 0.1770 0.035 Uiso 1 1 calc R U . . .
H9 H 0.0081 0.0556 0.1868 0.031 Uiso 1 1 calc R U . . .
H10 H -0.0181 -0.0350 0.3070 0.063 Uiso 1 1 calc R U . . .
H6 H 0.0995 0.1653 0.0249 0.044 Uiso 1 1 calc R U . . .
H30 H 0.6135 0.4052 0.0617 0.042 Uiso 1 1 calc R U . . .
H31 H 0.4829 0.3920 0.1478 0.044 Uiso 1 1 calc R U . . .
H32 H 0.4484 0.5361 0.2070 0.038 Uiso 1 1 calc R U . . .
H33 H 0.5564 0.6903 0.1797 0.036 Uiso 1 1 calc R U . . .
H34 H 0.6830 0.7041 0.0920 0.035 Uiso 1 1 calc R U . . .
H29 H 0.7472 0.4975 -0.0038 0.033 Uiso 1 1 calc R U . . .
H27 H 0.8952 0.6672 -0.0845 0.039 Uiso 1 1 calc R U . . .
H28 H 0.8552 0.5558 -0.0782 0.039 Uiso 1 1 calc R U . . .
H2 H 0.3354 0.4060 0.5740 0.032 Uiso 1 1 calc R U . . .
H4 H 0.4239 0.5264 0.7116 0.027 Uiso 1 1 calc R U . . .
H5 H 0.2910 0.7314 0.5899 0.035 Uiso 1 1 calc R U . . .
H3 H 0.4916 0.2596 0.7242 0.055 Uiso 1 1 calc R U . . .
H1 H 0.2167 0.5133 0.4636 0.057 Uiso 1 1 calc R U . . .
H14 H -0.0110 0.5572 0.2278 0.046 Uiso 1 1 calc R U . . .
H15 H -0.0247 0.4051 0.1800 0.057 Uiso 1 1 calc R U . . .
H16 H 0.0740 0.2290 0.2144 0.057 Uiso 1 1 calc R U . . .
H18 H 0.1655 0.2072 0.2984 0.048 Uiso 1 1 calc R U . . .
H17 H 0.1820 0.3606 0.3471 0.042 Uiso 1 1 calc R U . . .
H22 H 0.5320 0.2044 0.1710 0.037 Uiso 1 1 calc R U . . .
H23 H 0.5569 0.2244 0.0805 0.039 Uiso 1 1 calc R U . . .
H24 H 0.5949 0.0728 0.0254 0.036 Uiso 1 1 calc R U . . .
H25 H 0.5915 -0.0979 0.0625 0.033 Uiso 1 1 calc R U . . .
H26 H 0.5629 -0.1183 0.1526 0.033 Uiso 1 1 calc R U . . .
H13 H 0.0670 0.6319 0.3000 0.038 Uiso 1 1 calc R U . . .
H11 H 0.1336 0.7040 0.4152 0.047 Uiso 1 1 calc R U . . .
H12 H 0.0865 0.7427 0.3613 0.047 Uiso 1 1 calc R U . . .
H19 H 0.5366 0.0955 0.2428 0.036 Uiso 1 1 calc R U . . .
H20 H 0.4992 -0.0837 0.3328 0.047 Uiso 1 1 calc R U . . .
H21 H 0.5334 0.0279 0.3221 0.047 Uiso 1 1 calc R U . . .




_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C9 O9 1.227(7) . ?
C9 O10 1.316(7) . ?
C9 C10 1.492(8) . ?
C10 C15 1.377(8) . ?
C10 C11 1.383(8) . ?
C11 C12 1.381(8) . ?
C12 C13 1.401(9) . ?
C12 N2 1.484(8) . ?
C13 C14 1.378(9) . ?
C14 C15 1.399(8) . ?
C14 C16 1.485(9) . ?
C16 O7 1.233(7) . ?
C16 O8 1.299(8) . ?
N2 O11 1.217(7) . ?
N2 O12 1.239(7) . ?
C31 O15 1.245(7) . ?
C31 N8 1.328(8) . ?
C31 N7 1.372(7) . ?
C32 C33 1.371(8) . ?
C32 C37 1.375(8) . ?
C32 N7 1.431(8) . ?
C33 C34 1.378(9) . ?
C34 C35 1.380(9) . ?
C35 C36 1.379(8) . ?
C36 C37 1.400(9) . ?
C1 O5 1.214(8) . ?
C1 O6 1.314(7) . ?
C1 C2 1.488(9) . ?
C2 C3 1.389(9) . ?
C2 C7 1.401(9) . ?
C3 C4 1.370(8) . ?
C4 C5 1.394(8) . ?
C4 C8 1.508(8) . ?
C5 C6 1.387(8) . ?
C6 C7 1.368(9) . ?
C6 N1 1.464(8) . ?
C8 O2 1.220(7) . ?
C8 O1 1.295(7) . ?
N1 O3 1.221(7) . ?
N1 O4 1.234(7) . ?
C17 O13 1.252(7) . ?
C17 N4 1.339(8) . ?
C17 N3 1.356(8) . ?
C18 C23 1.369(9) . ?
C18 C19 1.394(9) . ?
C18 N3 1.415(8) . ?
C19 C20 1.375(10) . ?
C20 C21 1.385(11) . ?
C21 C22 1.362(10) . ?
C22 C23 1.406(9) . ?
C24 O14 1.258(7) . ?
C24 N6 1.339(8) . ?
C24 N5 1.353(8) . ?
C25 C26 1.372(8) . ?
C25 C30 1.400(8) . ?
C25 N5 1.424(8) . ?
C26 C27 1.383(9) . ?
C27 C28 1.385(9) . ?
C28 C29 1.390(8) . ?
C29 C30 1.374(8) . ?
C38 O16 1.272(16) . ?
C38 C39 1.63(2) . ?

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
O9 C9 O10 124.4(5) . . ?
O9 C9 C10 121.8(6) . . ?
O10 C9 C10 113.8(5) . . ?
C15 C10 C11 120.1(6) . . ?
C15 C10 C9 119.1(5) . . ?
C11 C10 C9 120.6(5) . . ?
C12 C11 C10 117.8(6) . . ?
C11 C12 C13 123.2(6) . . ?
C11 C12 N2 118.8(6) . . ?
C13 C12 N2 117.9(6) . . ?
C14 C13 C12 118.0(6) . . ?
C13 C14 C15 119.3(6) . . ?
C13 C14 C16 119.3(6) . . ?
C15 C14 C16 121.4(6) . . ?
C10 C15 C14 121.6(6) . . ?
O7 C16 O8 123.5(6) . . ?
O7 C16 C14 121.6(6) . . ?
O8 C16 C14 114.9(6) . . ?
O11 N2 O12 124.0(6) . . ?
O11 N2 C12 118.6(6) . . ?
O12 N2 C12 117.4(6) . . ?
O15 C31 N8 122.5(5) . . ?
O15 C31 N7 121.9(6) . . ?
N8 C31 N7 115.5(6) . . ?
C33 C32 C37 119.7(6) . . ?
C33 C32 N7 116.9(6) . . ?
C37 C32 N7 123.4(5) . . ?
C32 C33 C34 120.9(6) . . ?
C33 C34 C35 120.1(6) . . ?
C36 C35 C34 119.5(6) . . ?
C35 C36 C37 120.1(6) . . ?
C32 C37 C36 119.7(6) . . ?
C31 N7 C32 129.3(5) . . ?
O5 C1 O6 124.5(6) . . ?
O5 C1 C2 123.2(6) . . ?
O6 C1 C2 112.4(6) . . ?
C3 C2 C7 118.6(6) . . ?
C3 C2 C1 121.8(6) . . ?
C7 C2 C1 119.6(6) . . ?
C4 C3 C2 121.6(6) . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 C8 119.0(6) . . ?
C5 C4 C8 120.9(5) . . ?
C6 C5 C4 117.9(6) . . ?
C7 C6 C5 122.7(6) . . ?
C7 C6 N1 118.6(6) . . ?
C5 C6 N1 118.6(6) . . ?
C6 C7 C2 119.0(6) . . ?
O2 C8 O1 124.4(6) . . ?
O2 C8 C4 121.5(6) . . ?
O1 C8 C4 114.0(5) . . ?
O3 N1 O4 123.2(6) . . ?
O3 N1 C6 119.8(6) . . ?
O4 N1 C6 116.9(6) . . ?
O13 C17 N4 122.6(6) . . ?
O13 C17 N3 122.2(6) . . ?
N4 C17 N3 115.2(6) . . ?
C23 C18 C19 119.4(6) . . ?
C23 C18 N3 124.9(6) . . ?
C19 C18 N3 115.6(6) . . ?
C20 C19 C18 120.3(7) . . ?
C19 C20 C21 120.3(7) . . ?
C22 C21 C20 119.7(7) . . ?
C21 C22 C23 120.4(7) . . ?
C18 C23 C22 119.9(7) . . ?
O14 C24 N6 121.1(6) . . ?
O14 C24 N5 121.9(6) . . ?
N6 C24 N5 116.9(6) . . ?
C26 C25 C30 119.9(6) . . ?
C26 C25 N5 116.7(6) . . ?
C30 C25 N5 123.3(5) . . ?
C25 C26 C27 120.0(6) . . ?
C26 C27 C28 120.9(6) . . ?
C27 C28 C29 118.7(6) . . ?
C30 C29 C28 120.9(6) . . ?
C29 C30 C25 119.6(6) . . ?
C17 N3 C18 128.0(6) . . ?
C24 N5 C25 129.7(5) . . ?
O16 C38 C39 111.0(14) . . ?

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
O8 H10 O16 0.82 1.79 2.611(9) 176.1 1_445
O10 H6 O15 0.82 1.81 2.580(6) 156.6 2_665
C33 H30 O11 0.93 2.65 3.496(8) 150.9 2_655
C37 H34 O15 0.93 2.26 2.872(8) 123.1 .
N7 H29 O11 0.86 2.54 3.371(7) 162.3 2_655
N8 H27 O9 0.86 2.06 2.904(6) 165.8 2_665
N8 H28 O12 0.86 2.18 3.020(7) 166.6 2_655
O1 H3 O14 0.82 1.73 2.534(6) 166.5 2_656
O6 H1 O13 0.82 1.71 2.514(6) 164.8 .
C23 H17 O13 0.93 2.25 2.849(8) 121.5 .
C30 H26 O14 0.93 2.30 2.890(7) 121.1 .
N3 H13 O7 0.86 2.08 2.923(7) 165.3 1_565
N4 H11 O5 0.86 2.23 3.061(7) 161.5 .
N4 H12 O7 0.86 2.39 3.150(7) 146.7 1_565
N4 H12 O16 0.86 2.56 3.177(9) 129.7 1_455
N5 H19 O3 0.86 2.55 3.384(7) 164.7 2_666
N6 H20 O2 0.86 2.18 2.961(7) 150.8 2_656
N6 H21 O4 0.86 2.20 3.043(7) 167.0 2_666

_refine_diff_density_max         1.124
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethanol
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM3
_database_code_depnum_ccdc_archive 'CCDC 1471784'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'tris(n-phenylurea) bis(5-nitroisophthalic acid) acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C7 H8 N2 O1), 2(C8 H5 N1 O6),  C2 H3 N1'
_chemical_formula_sum            'C39 H37 N9 O15'
_chemical_formula_weight         871.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0887(5)
_cell_length_b                   12.3161(5)
_cell_length_c                   17.3345(10)
_cell_angle_alpha                70.478(5)
_cell_angle_beta                 87.122(4)
_cell_angle_gamma                87.659(4)
_cell_volume                     2026.83(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(14)
_cell_measurement_reflns_used    5351
_cell_measurement_theta_min      3.8400
_cell_measurement_theta_max      73.3690
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             908
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_min  0.94939
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;
_diffrn_ambient_temperature      150
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_number            14449
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         74.405
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7975
_reflns_number_gt                6311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.3012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7975
_refine_ls_number_parameters     716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.04849(12) 0.85246(9) 0.15319(8) 0.0372(3) Uani 1 1 d . . . . .
O2 O 0.92285(11) 0.62846(9) 0.34208(7) 0.0309(2) Uani 1 1 d . . . . .
O3 O 0.50441(11) 0.50791(9) 0.11006(7) 0.0317(2) Uani 1 1 d . . . . .
O4 O 0.69307(11) 0.42766(9) 0.20494(7) 0.0326(3) Uani 1 1 d . . . . .
O5 O 0.50814(11) 0.83956(9) 0.38527(7) 0.0324(2) Uani 1 1 d . . . . .
O6 O 0.04458(12) 0.94060(9) -0.10883(8) 0.0368(3) Uani 1 1 d . . . . .
O7 O 0.95012(12) 0.80784(9) 0.34224(8) 0.0360(3) Uani 1 1 d . . . . .
O8 O 1.39671(11) 0.36643(9) 0.56614(8) 0.0346(3) Uani 1 1 d . . . . .
O9 O 0.53856(12) 0.68920(9) 0.10427(8) 0.0360(3) Uani 1 1 d . . . . .
O10 O 0.19628(12) 0.98613(9) -0.03526(8) 0.0373(3) Uani 1 1 d . . . . .
O11 O 1.23973(12) 0.32057(9) 0.49602(8) 0.0356(3) Uani 1 1 d . . . . .
O12 O 1.40371(12) 0.75100(11) 0.58195(8) 0.0405(3) Uani 1 1 d . . . . .
O13 O 0.02623(12) 0.54248(10) -0.10377(8) 0.0379(3) Uani 1 1 d . . . . .
O14 O 1.27570(13) 0.88583(10) 0.50604(8) 0.0402(3) Uani 1 1 d . . . . .
O15 O 0.17274(13) 0.41708(10) -0.03819(8) 0.0419(3) Uani 1 1 d . . . . .
N1 N 0.85505(13) 0.42403(11) 0.29315(8) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.06780(13) 0.66391(11) 0.16124(8) 0.0280(3) Uani 1 1 d . . . . .
N8 N 0.12451(13) 0.51551(11) -0.06200(8) 0.0307(3) Uani 1 1 d . . . . .
N3 N -0.08850(14) 0.78403(12) 0.08192(9) 0.0336(3) Uani 1 1 d . . . . .
N4 N 1.31682(14) 0.78544(11) 0.53173(9) 0.0318(3) Uani 1 1 d . . . . .
N5 N 0.50891(15) 1.03323(12) 0.36251(9) 0.0354(3) Uani 1 1 d . . . . .
N6 N 0.64257(18) 0.90938(13) 0.45711(11) 0.0457(4) Uani 1 1 d . . . . .
N7 N 0.73213(14) 0.58874(12) 0.23458(9) 0.0336(3) Uani 1 1 d . . . . .
N9 N 0.73643(16) 0.87012(15) 0.24153(10) 0.0474(4) Uani 1 1 d . . . . .
C38 C 1.09369(14) 0.66201(12) 0.42042(9) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.18807(15) 0.60350(13) -0.03810(9) 0.0275(3) Uani 1 1 d . . . . .
C3 C 1.24607(14) 0.51283(12) 0.49594(9) 0.0246(3) Uani 1 1 d . . . . .
C4 C 1.25681(15) 0.70310(13) 0.50038(9) 0.0271(3) Uani 1 1 d . . . . .
C5 C 0.35855(15) 0.65207(13) 0.03366(9) 0.0263(3) Uani 1 1 d . . . . .
C6 C 1.15238(15) 0.74064(12) 0.44867(9) 0.0262(3) Uani 1 1 d . . . . .
C7 C 0.89945(15) 0.30765(13) 0.31497(9) 0.0278(3) Uani 1 1 d . . . . .
C8 C 1.30563(15) 0.59037(13) 0.52488(9) 0.0260(3) Uani 1 1 d . . . . .
C9 C 0.75616(14) 0.47808(13) 0.24250(9) 0.0262(3) Uani 1 1 d . . . . .
C10 C 0.01038(15) 0.77150(13) 0.13308(9) 0.0277(3) Uani 1 1 d . . . . .
C11 C 0.29683(15) 0.56981(13) 0.01058(9) 0.0263(3) Uani 1 1 d . . . . .
C12 C 0.19827(15) 0.79630(12) -0.03911(9) 0.0267(3) Uani 1 1 d . . . . .
C13 C 0.17731(15) 0.62635(13) 0.21175(9) 0.0282(3) Uani 1 1 d . . . . .
C14 C 1.14038(15) 0.54812(12) 0.44428(9) 0.0255(3) Uani 1 1 d . . . . .
C15 C 0.98013(15) 0.69707(12) 0.36441(9) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.30897(15) 0.76475(13) 0.00919(9) 0.0264(3) Uani 1 1 d . . . . .
C35 C 0.47692(15) 0.61912(13) 0.08643(9) 0.0268(3) Uani 1 1 d . . . . .
C17 C 0.25616(16) 0.69939(15) 0.23506(10) 0.0336(3) Uani 1 1 d . . . . .
C18 C 0.13648(15) 0.71522(13) -0.06428(9) 0.0268(3) Uani 1 1 d . . . . .
C19 C 1.29406(15) 0.38966(12) 0.51933(9) 0.0264(3) Uani 1 1 d . . . . .
C20 C 0.42216(17) 1.07208(13) 0.29673(11) 0.0345(4) Uani 1 1 d . . . . .
C21 C 0.14582(15) 0.91825(13) -0.06104(10) 0.0290(3) Uani 1 1 d . . . . .
C22 C 0.55200(16) 0.92282(13) 0.40094(10) 0.0306(3) Uani 1 1 d . . . . .
C23 C 0.84426(17) 0.22621(14) 0.28717(11) 0.0342(3) Uani 1 1 d . . . . .
C24 C 1.00345(17) 0.27449(15) 0.36865(11) 0.0353(4) Uani 1 1 d . . . . .
C25 C 0.31979(18) 1.00638(15) 0.28643(12) 0.0391(4) Uani 1 1 d . . . . .
C26 C 0.20750(17) 0.50853(14) 0.23764(10) 0.0336(3) Uani 1 1 d . . . . .
C27 C 0.4395(2) 1.18227(16) 0.24170(15) 0.0547(6) Uani 1 1 d . . . . .
C28 C 0.36480(17) 0.65397(17) 0.28319(11) 0.0394(4) Uani 1 1 d . . . . .
C29 C 0.39497(17) 0.53722(18) 0.30826(11) 0.0413(4) Uani 1 1 d . . . . .
C30 C 0.2377(2) 1.05033(17) 0.22106(14) 0.0487(5) Uani 1 1 d . . . . .
C31 C 0.64956(18) 0.89659(15) 0.19951(11) 0.0386(4) Uani 1 1 d . . . . .
C32 C 0.31590(19) 0.46466(16) 0.28563(11) 0.0408(4) Uani 1 1 d . . . . .
C33 C 0.8926(2) 0.11292(15) 0.31472(12) 0.0425(4) Uani 1 1 d . . . . .
C34 C 0.5388(2) 0.93034(19) 0.14508(15) 0.0449(4) Uani 1 1 d . . . . .
C40 C 0.9940(2) 0.08042(16) 0.36881(14) 0.0496(5) Uani 1 1 d . . . . .
C39 C 1.0499(2) 0.16149(17) 0.39551(14) 0.0474(5) Uani 1 1 d . . . . .
C36 C 0.2560(2) 1.15979(19) 0.16554(16) 0.0622(6) Uani 1 1 d . . . . .
C37 C 0.3562(3) 1.22549(19) 0.17652(19) 0.0736(8) Uani 1 1 d . . . . .
H3 H 0.3270(17) 0.4927(16) 0.0260(11) 0.026(4) Uiso 1 1 d . . . . .
H9 H 1.1008(18) 0.4951(15) 0.4221(11) 0.027(4) Uiso 1 1 d . . . . .
H1 H 0.0628(19) 0.7332(15) -0.0973(11) 0.028(4) Uiso 1 1 d . . . . .
H2 H 0.3492(19) 0.8211(17) 0.0255(12) 0.033(5) Uiso 1 1 d . . . . .
H10 H 1.1218(18) 0.8172(17) 0.4339(11) 0.030(5) Uiso 1 1 d . . . . .
H11 H 1.3798(19) 0.5680(15) 0.5596(11) 0.029(4) Uiso 1 1 d . . . . .
H7 H 1.043(2) 0.3310(17) 0.3861(12) 0.038(5) Uiso 1 1 d . . . . .
H18 H 0.235(2) 0.7812(18) 0.2182(13) 0.040(5) Uiso 1 1 d . . . . .
H17 H 0.1527(19) 0.4592(16) 0.2200(11) 0.031(5) Uiso 1 1 d . . . . .
H5 H 0.778(2) 0.6255(17) 0.2626(12) 0.037(5) Uiso 1 1 d . . . . .
H6 H 0.896(2) 0.4660(18) 0.3164(13) 0.038(5) Uiso 1 1 d . . . . .
H8 H 0.772(2) 0.2487(17) 0.2494(13) 0.038(5) Uiso 1 1 d . . . . .
H14 H -0.132(2) 0.8496(19) 0.0645(13) 0.038(5) Uiso 1 1 d . . . . .
H19 H 0.422(2) 0.7049(17) 0.3004(12) 0.040(5) Uiso 1 1 d . . . . .
H16 H 0.0346(19) 0.6126(17) 0.1469(12) 0.032(5) Uiso 1 1 d . . . . .
H4 H 0.674(2) 0.6278(17) 0.1981(12) 0.033(5) Uiso 1 1 d . . . . .
H12 H 0.679(2) 0.844(2) 0.4765(13) 0.044(6) Uiso 1 1 d . . . . .
H13 H 0.674(2) 0.967(2) 0.4645(13) 0.044(6) Uiso 1 1 d . . . . .
H15 H -0.114(2) 0.7258(19) 0.0711(12) 0.037(5) Uiso 1 1 d . . . . .
H26 H 0.850(2) 0.0556(19) 0.2948(14) 0.049(6) Uiso 1 1 d . . . . .
H24 H 1.125(2) 0.141(2) 0.4330(15) 0.055(6) Uiso 1 1 d . . . . .
H28 H 0.309(2) 0.9298(19) 0.3250(13) 0.041(5) Uiso 1 1 d . . . . .
H22 H 0.878(2) 0.823(2) 0.3096(14) 0.050(6) Uiso 1 1 d . . . . .
H20 H 0.575(3) 0.487(2) 0.1457(16) 0.061(7) Uiso 1 1 d . . . . .
H29 H 0.163(2) 1.004(2) 0.2124(14) 0.051(6) Uiso 1 1 d . . . . .
H32 H 0.509(2) 1.2272(19) 0.2494(14) 0.050(6) Uiso 1 1 d . . . . .
H27 H 0.546(2) 1.0829(19) 0.3745(13) 0.043(6) Uiso 1 1 d . . . . .
H23 H 1.426(2) 0.290(2) 0.5801(15) 0.055(6) Uiso 1 1 d . . . . .
H21 H 0.016(2) 1.016(2) -0.1226(15) 0.061(7) Uiso 1 1 d . . . . .
H25 H 1.029(3) 0.002(2) 0.3870(15) 0.066(7) Uiso 1 1 d . . . . .
H30 H 0.194(3) 1.190(2) 0.1202(17) 0.077(8) Uiso 1 1 d . . . . .
H31 H 0.374(3) 1.300(3) 0.1404(19) 0.090(10) Uiso 1 1 d . . . . .
H100 H 0.505(4) 1.001(3) 0.140(2) 0.110(12) Uiso 1 1 d . . . . .
H102 H 0.563(4) 0.934(3) 0.093(3) 0.115(13) Uiso 1 1 d . . . . .
H101 H 0.472(5) 0.886(4) 0.162(3) 0.139(16) Uiso 1 1 d . . . . .
H103 H 0.337(2) 0.383(2) 0.3045(14) 0.050(6) Uiso 1 1 d . . . . .
H104 H 0.470(2) 0.5068(19) 0.3406(14) 0.050(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C10 1.2412(19) . ?
O2 C15 1.2161(18) . ?
O3 C35 1.3138(18) . ?
O4 C9 1.2485(18) . ?
O5 C22 1.2476(18) . ?
O6 C21 1.3095(19) . ?
O7 C15 1.3146(18) . ?
O8 C19 1.3106(18) . ?
O9 C35 1.2120(19) . ?
O10 C21 1.2104(19) . ?
O11 C19 1.2156(18) . ?
O12 N4 1.2271(18) . ?
O13 N8 1.2256(18) . ?
O14 N4 1.2279(18) . ?
O15 N8 1.2306(18) . ?
N1 C9 1.3611(19) . ?
N1 C7 1.4143(19) . ?
N2 C10 1.3650(19) . ?
N2 C13 1.4093(19) . ?
N8 C2 1.4631(19) . ?
N3 C10 1.338(2) . ?
N4 C4 1.4634(18) . ?
N5 C22 1.363(2) . ?
N5 C20 1.413(2) . ?
N6 C22 1.334(2) . ?
N7 C9 1.336(2) . ?
N9 C31 1.134(2) . ?
C38 C6 1.386(2) . ?
C38 C14 1.392(2) . ?
C38 C15 1.494(2) . ?
C2 C11 1.382(2) . ?
C2 C18 1.385(2) . ?
C3 C8 1.386(2) . ?
C3 C14 1.388(2) . ?
C3 C19 1.500(2) . ?
C4 C6 1.380(2) . ?
C4 C8 1.386(2) . ?
C5 C11 1.386(2) . ?
C5 C16 1.388(2) . ?
C5 C35 1.500(2) . ?
C7 C24 1.394(2) . ?
C7 C23 1.394(2) . ?
C12 C16 1.393(2) . ?
C12 C18 1.395(2) . ?
C12 C21 1.501(2) . ?
C13 C17 1.392(2) . ?
C13 C26 1.394(2) . ?
C17 C28 1.393(2) . ?
C20 C27 1.386(3) . ?
C20 C25 1.392(2) . ?
C23 C33 1.391(2) . ?
C24 C39 1.382(2) . ?
C25 C30 1.382(3) . ?
C26 C32 1.387(2) . ?
C27 C37 1.387(3) . ?
C28 C29 1.382(3) . ?
C29 C32 1.383(3) . ?
C30 C36 1.383(3) . ?
C31 C34 1.455(3) . ?
C33 C40 1.378(3) . ?
C40 C39 1.382(3) . ?
C36 C37 1.379(3) . ?

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
C9 N1 C7 128.44(13) . . ?
C10 N2 C13 128.55(13) . . ?
O13 N8 O15 123.27(13) . . ?
O13 N8 C2 119.07(13) . . ?
O15 N8 C2 117.66(13) . . ?
O12 N4 O14 123.84(13) . . ?
O12 N4 C4 118.90(13) . . ?
O14 N4 C4 117.25(13) . . ?
C22 N5 C20 127.16(13) . . ?
C6 C38 C14 119.97(13) . . ?
C6 C38 C15 121.15(13) . . ?
C14 C38 C15 118.88(13) . . ?
C11 C2 C18 123.29(14) . . ?
C11 C2 N8 117.68(13) . . ?
C18 C2 N8 119.02(13) . . ?
C8 C3 C14 120.37(13) . . ?
C8 C3 C19 121.08(13) . . ?
C14 C3 C19 118.55(13) . . ?
C6 C4 C8 122.77(13) . . ?
C6 C4 N4 118.51(13) . . ?
C8 C4 N4 118.71(13) . . ?
C11 C5 C16 119.86(13) . . ?
C11 C5 C35 120.18(13) . . ?
C16 C5 C35 119.94(13) . . ?
C4 C6 C38 118.49(13) . . ?
C24 C7 C23 119.40(14) . . ?
C24 C7 N1 116.58(14) . . ?
C23 C7 N1 124.00(13) . . ?
C4 C8 C3 118.05(13) . . ?
O4 C9 N7 122.14(13) . . ?
O4 C9 N1 121.95(13) . . ?
N7 C9 N1 115.91(13) . . ?
O1 C10 N3 122.37(14) . . ?
O1 C10 N2 122.00(14) . . ?
N3 C10 N2 115.63(13) . . ?
C2 C11 C5 118.49(13) . . ?
C16 C12 C18 120.38(13) . . ?
C16 C12 C21 118.25(13) . . ?
C18 C12 C21 121.35(13) . . ?
C17 C13 C26 119.47(14) . . ?
C17 C13 N2 124.11(14) . . ?
C26 C13 N2 116.41(14) . . ?
C3 C14 C38 120.36(13) . . ?
O2 C15 O7 124.33(14) . . ?
O2 C15 C38 122.31(13) . . ?
O7 C15 C38 113.36(12) . . ?
C5 C16 C12 120.56(14) . . ?
O9 C35 O3 125.05(13) . . ?
O9 C35 C5 122.47(13) . . ?
O3 C35 C5 112.48(12) . . ?
C13 C17 C28 119.63(16) . . ?
C2 C18 C12 117.40(13) . . ?
O11 C19 O8 125.14(13) . . ?
O11 C19 C3 121.31(13) . . ?
O8 C19 C3 113.54(12) . . ?
C27 C20 C25 119.42(16) . . ?
C27 C20 N5 117.39(15) . . ?
C25 C20 N5 123.17(16) . . ?
O10 C21 O6 125.64(14) . . ?
O10 C21 C12 120.64(13) . . ?
O6 C21 C12 113.73(13) . . ?
O5 C22 N6 122.21(15) . . ?
O5 C22 N5 122.03(14) . . ?
N6 C22 N5 115.75(14) . . ?
C33 C23 C7 119.31(15) . . ?
C39 C24 C7 120.47(16) . . ?
C30 C25 C20 120.09(17) . . ?
C32 C26 C13 120.19(16) . . ?
C20 C27 C37 119.90(19) . . ?
C29 C28 C17 120.74(17) . . ?
C28 C29 C32 119.56(16) . . ?
C25 C30 C36 120.49(18) . . ?
N9 C31 C34 179.5(2) . . ?
C29 C32 C26 120.41(17) . . ?
C40 C33 C23 120.93(17) . . ?
C33 C40 C39 119.76(16) . . ?
C24 C39 C40 120.11(17) . . ?
C37 C36 C30 119.36(19) . . ?
C36 C37 C27 120.7(2) . . ?

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
C17 H18 O1 0.97(2) 2.24(2) 2.854(2) 120.5(16) .
N7 H5 O2 0.92(2) 2.07(2) 2.9087(17) 151.9(18) .
N1 H6 O2 0.88(2) 2.22(2) 3.0254(16) 152.1(18) .
C23 H8 O4 0.98(2) 2.20(2) 2.839(2) 121.4(15) .
N3 H14 O10 0.87(2) 2.00(2) 2.8559(17) 166.5(19) 2_575
N2 H16 O13 0.84(2) 2.38(2) 3.2152(17) 171.4(18) 2_565
N7 H4 O9 0.89(2) 2.10(2) 2.9706(17) 167.9(18) .
N6 H12 O11 0.84(2) 2.06(2) 2.8939(19) 170(2) 2_766
N6 H13 O14 0.84(2) 2.13(2) 2.9580(18) 171(2) 2_776
N3 H15 O15 0.85(2) 2.14(2) 2.9873(18) 177(2) 2_565
C25 H28 O5 0.96(2) 2.37(2) 2.902(2) 114.3(15) .
O7 H22 N9 0.92(2) 1.85(2) 2.762(2) 174(2) .
O3 H20 O4 0.94(3) 1.59(3) 2.5256(15) 169(2) .
N5 H27 O12 0.82(2) 2.48(2) 3.2791(17) 164(2) 2_776
O8 H23 O5 0.93(2) 1.63(3) 2.5538(15) 171(2) 2_766
O6 H21 O1 0.92(3) 1.64(3) 2.5566(15) 174(2) 2_575

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1471785'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014

# start Validation Reply Form
_vrf_PLAT026_shelx               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low .. 37 %
RESPONSE: Weakly diffracting crystals are a likely 
cause of this problem.  Despite efforts, larger crystals could be obtained.
;
_vrf_PLAT417_shelx               
;
PROBLEM: Short Inter D-H..H-D H2 .. H53 .. 2.03 Ang.
RESPONSE: Contact is to a water solvent molecule.
;
_vrf_PLAT910_shelx               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min) 16 Note
RESPONSE: Weakly diffracting crystals are a likely 
cause of this problem.  Despite efforts, larger crystals could be obtained.
;
# end Validation Reply Form


_chemical_name_systematic        
"'tris(n-phenylurea) bis(5-nitroisophthalic acid) acetone solvate hydrate"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C8 H5 N1 O6), 3(C7 H8 N2 O1), C3 H6 O1, H2 O1'
_chemical_formula_sum            'C40 H42 N8 O17'
_chemical_formula_weight         906.81

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3639(7)
_cell_length_b                   13.0486(10)
_cell_length_c                   13.8208(10)
_cell_angle_alpha                71.686(7)
_cell_angle_beta                 89.156(5)
_cell_angle_gamma                87.439(5)
_cell_volume                     2114.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1353
_cell_measurement_theta_min      3.7110
_cell_measurement_theta_max      21.8150

_exptl_crystal_description       'triangular plate'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_min  0.91254
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_reflns_number            15519
_diffrn_reflns_av_unetI/netI     0.2367
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.292
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             7467
_reflns_number_gt                2728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

The N--H distance in secondary amine groups N7 H52 and N2 H51 was fixed at 0.86 angstroms.
In the water molecule, the O--H distances were fixed at 0.82 angstroms and the HOH angle fixed
using DANG 1.319. 

The 5-nitroisophthalic acid hydroxyl hydrogen atoms were all fixed in a riding position (HFIX 83).

A number of the aromatic C--H groups were fixed in riding positions using HFIX 43.

The acetone methyl hydrogen atoms (both methyl groups) were fixed in a riding position using HFIX 137. 

The hydrogen atoms in the primary amine groups of n-phenylurea were fixed in riding positions using HFIX 93. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7467
_refine_ls_number_parameters     606
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.2373
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2000
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0601(3) 0.4033(3) 0.4612(3) 0.0296(11) Uani 1 1 d . . . . .
H1 H 0.0513 0.4316 0.3997 0.044 Uiso 1 1 calc R U . . .
O2 O 0.6088(3) 0.5902(3) 0.0173(3) 0.0317(12) Uani 1 1 d . . . . .
H2 H 0.6171 0.5600 0.0785 0.048 Uiso 1 1 calc R U . . .
O3 O 0.1874(3) 0.1804(4) 0.9187(3) 0.0321(12) Uani 1 1 d . . . . .
H60 H 0.2479 0.1765 0.9435 0.048 Uiso 1 1 calc R U . . .
O4 O 0.0645(3) 0.4886(3) 0.2716(3) 0.0289(11) Uani 1 1 d . . . . .
O5 O 0.2970(3) 0.9070(4) 0.4792(3) 0.0381(13) Uani 1 1 d . . . . .
O6 O -0.2012(3) 0.1370(4) 0.9236(3) 0.0366(12) Uani 1 1 d . . . . .
O7 O 0.4814(3) 0.8490(4) -0.4322(3) 0.0387(13) Uani 1 1 d . . . . .
H42 H 0.4193 0.8607 -0.4542 0.058 Uiso 1 1 calc R U . . .
O8 O 0.9693(3) 0.7542(3) -0.3084(3) 0.0351(12) Uani 1 1 d . . . . .
O9 O -0.2948(3) 0.2100(4) 0.7854(3) 0.0371(13) Uani 1 1 d . . . . .
O10 O 0.3984(3) 0.7430(4) -0.2926(3) 0.0455(14) Uani 1 1 d . . . . .
O11 O 0.3716(3) 0.1496(3) 0.0105(3) 0.0282(11) Uani 1 1 d . . . . .
O12 O -0.1173(3) 0.3747(4) 0.4580(3) 0.0355(12) Uani 1 1 d . . . . .
O13 O 0.7907(3) 0.6006(3) 0.0195(3) 0.0295(11) Uani 1 1 d . . . . .
O14 O 0.2682(3) 0.2853(4) 0.7764(3) 0.0356(12) Uani 1 1 d . . . . .
O15 O 0.8776(3) 0.8316(4) -0.4464(3) 0.0366(12) Uani 1 1 d . . . . .
N2 N 0.5546(4) 0.1121(4) 0.0219(4) 0.0249(13) Uani 1 1 d D . . . .
N3 N 0.4777(3) 0.2150(4) -0.1296(4) 0.0283(14) Uani 1 1 d . . . . .
H3A H 0.4237 0.2470 -0.1673 0.034 Uiso 1 1 calc R U . . .
H3B H 0.5419 0.2190 -0.1550 0.034 Uiso 1 1 calc R U . . .
N4 N 0.1929(4) 0.8257(4) 0.6166(4) 0.0317(15) Uani 1 1 d . . . . .
H4A H 0.2482 0.8074 0.6564 0.038 Uiso 1 1 calc R U . . .
H4B H 0.1292 0.8089 0.6402 0.038 Uiso 1 1 calc R U . . .
N5 N 0.8835(4) 0.7813(4) -0.3551(4) 0.0269(14) Uani 1 1 d . . . . .
N6 N 0.1130(4) 0.9091(5) 0.4611(4) 0.0254(14) Uani 1 1 d . . . . .
N7 N 0.0071(4) 0.5598(4) 0.1078(4) 0.0258(14) Uani 1 1 d D . . . .
N8 N -0.2075(4) 0.1882(5) 0.8322(4) 0.0301(14) Uani 1 1 d . . . . .
N10 N -0.1127(3) 0.4828(4) 0.2345(4) 0.0296(14) Uani 1 1 d . . . . .
H10A H -0.1284 0.4506 0.2973 0.036 Uiso 1 1 calc R U . . .
H10B H -0.1625 0.4981 0.1889 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1639(4) 1.0506(5) 0.1874(5) 0.0270(16) Uani 1 1 d . . . . .
H3 H 0.2215 1.0719 0.1425 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7035(5) 0.6163(5) -0.0259(5) 0.0246(16) Uani 1 1 d . . . . .
C5 C 0.1912(5) 0.7022(5) -0.0969(5) 0.0336(17) Uani 1 1 d . . . . .
H5 H 0.1859 0.7407 -0.1659 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2062(5) 0.8800(5) 0.5185(5) 0.0246(16) Uani 1 1 d . . . . .
C7 C 0.7881(4) 0.6976(5) -0.1943(5) 0.0217(15) Uani 1 1 d . . . . .
H7 H 0.8553 0.6783 -0.1629 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7825(4) 0.7519(5) -0.2979(5) 0.0234(16) Uani 1 1 d . . . . .
C9 C 0.2051(4) 0.5867(5) 0.1086(5) 0.0236(16) Uani 1 1 d . . . . .
H9 H 0.2106 0.5476 0.1775 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6954(4) 0.6720(5) -0.1375(4) 0.0206(15) Uani 1 1 d . . . . .
C11 C 0.4618(4) 0.1587(5) -0.0310(5) 0.0222(15) Uani 1 1 d . . . . .
C12 C 0.0584(5) 1.0742(5) 0.1508(5) 0.0325(17) Uani 1 1 d . . . . .
H12 H 0.0447 1.1099 0.0821 0.039 Uiso 1 1 calc R U . . .
C13 C 0.0999(4) 0.9649(5) 0.3565(5) 0.0203(15) Uani 1 1 d . . . . .
C14 C 0.1047(4) 0.6029(5) 0.0597(5) 0.0204(15) Uani 1 1 d . . . . .
C15 C -0.0324(5) 0.3669(5) 0.5038(5) 0.0240(15) Uani 1 1 d . . . . .
C16 C -0.0235(4) 0.3140(5) 0.6163(4) 0.0191(15) Uani 1 1 d . . . . .
C17 C 0.6844(4) 0.7813(5) -0.3458(5) 0.0243(16) Uani 1 1 d . . . . .
H17 H 0.6813 0.8192 -0.4151 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6714(4) 0.0164(5) 0.1589(5) 0.0281(17) Uani 1 1 d . . . . .
H18 H 0.7282 0.0298 0.1123 0.034 Uiso 1 1 calc R U . . .
C19 C 0.2905(5) 0.6865(5) -0.0491(5) 0.0295(17) Uani 1 1 d . . . . .
H19 H 0.3524 0.7138 -0.0854 0.035 Uiso 1 1 calc R U . . .
C20 C -0.0063(4) 0.9881(5) 0.3221(5) 0.0245(16) Uani 1 1 d . . . . .
H20 H -0.0637 0.9669 0.3672 0.029 Uiso 1 1 calc R U . . .
C21 C 0.1895(5) 0.2410(5) 0.8214(5) 0.0251(16) Uani 1 1 d . . . . .
C22 C 0.5910(4) 0.7544(5) -0.2911(5) 0.0206(15) Uani 1 1 d . . . . .
C23 C -0.0257(5) 1.0428(5) 0.2201(5) 0.0312(17) Uani 1 1 d . . . . .
H23 H -0.0968 1.0590 0.1975 0.037 Uiso 1 1 calc R U . . .
C24 C 0.2964(5) 0.6293(5) 0.0540(5) 0.0311(17) Uani 1 1 d . . . . .
H24 H 0.3628 0.6194 0.0870 0.037 Uiso 1 1 calc R U . . .
C25 C 0.0811(4) 0.2513(5) 0.7716(4) 0.0200(15) Uani 1 1 d . . . . .
C26 C 0.0752(4) 0.3020(5) 0.6674(4) 0.0203(15) Uani 1 1 d . . . . .
H26 H 0.1374 0.3283 0.6311 0.024 Uiso 1 1 calc R U . . .
C27 C 0.5662(4) 0.0525(5) 0.1271(5) 0.0234(16) Uani 1 1 d . . . . .
C28 C 0.0992(5) 0.6613(5) -0.0429(5) 0.0290(17) Uani 1 1 d . . . . .
H28 H 0.0327 0.6731 -0.0761 0.035 Uiso 1 1 calc R U . . .
C29 C -0.1088(4) 0.2260(5) 0.7740(5) 0.0264(16) Uani 1 1 d . . . . .
C30 C -0.0117(4) 0.2118(5) 0.8268(5) 0.0214(15) Uani 1 1 d . . . . .
H30 H -0.0087 0.1771 0.8968 0.026 Uiso 1 1 calc R U . . .
C31 C -0.1157(4) 0.2745(5) 0.6708(5) 0.0231(15) Uani 1 1 d . . . . .
H31 H -0.1817 0.2809 0.6376 0.028 Uiso 1 1 calc R U . . .
C32 C 0.1853(4) 0.9958(5) 0.2895(4) 0.0249(16) Uani 1 1 d . . . . .
H32 H 0.2564 0.9801 0.3124 0.030 Uiso 1 1 calc R U . . .
C33 C 0.5961(4) 0.6973(5) -0.1866(4) 0.0234(16) Uani 1 1 d . . . . .
H33 H 0.5327 0.6763 -0.1501 0.028 Uiso 1 1 calc R U . . .
C34 C 0.4816(5) 0.0301(6) 0.1952(5) 0.0351(19) Uani 1 1 d . . . . .
H34 H 0.4111 0.0524 0.1736 0.042 Uiso 1 1 calc R U . . .
C35 C 0.6903(5) -0.0392(6) 0.2594(5) 0.0375(19) Uani 1 1 d . . . . .
H35 H 0.7609 -0.0612 0.2809 0.045 Uiso 1 1 calc R U . . .
C36 C 0.4807(5) 0.7813(6) -0.3385(5) 0.0299(17) Uani 1 1 d . . . . .
C37 C -0.0100(5) 0.5093(5) 0.2078(5) 0.0271(16) Uani 1 1 d . . . . .
C38 C 0.5031(5) -0.0262(6) 0.2963(5) 0.045(2) Uani 1 1 d . . . . .
H38 H 0.4464 -0.0394 0.3430 0.054 Uiso 1 1 calc R U . . .
C39 C 0.6072(5) -0.0635(6) 0.3300(5) 0.041(2) Uani 1 1 d . . . . .
H39 H 0.6206 -0.1035 0.3977 0.049 Uiso 1 1 calc R U . . .
C100 C 0.4179(8) 0.6580(8) 0.4472(8) 0.122(4) Uani 1 1 d . . . . .
H10C H 0.4850 0.6514 0.4832 0.183 Uiso 1 1 calc R U . . .
H10D H 0.3587 0.6506 0.4943 0.183 Uiso 1 1 calc R U . . .
H10E H 0.4118 0.7276 0.3961 0.183 Uiso 1 1 calc R U . . .
C40 C 0.4150(11) 0.5656(9) 0.3941(8) 0.109(4) Uani 1 1 d . . . . .
O17 O 0.6308(4) 0.4843(5) 0.2123(4) 0.0511(15) Uani 1 1 d D . . . .
C101 C 0.3255(8) 0.4808(12) 0.4349(15) 0.262(11) Uani 1 1 d . . . . .
H10F H 0.3045 0.4533 0.3816 0.393 Uiso 1 1 calc R U . . .
H10G H 0.2637 0.5149 0.4569 0.393 Uiso 1 1 calc R U . . .
H10H H 0.3537 0.4224 0.4914 0.393 Uiso 1 1 calc R U . . .
O100 O 0.4918(8) 0.5506(11) 0.3445(7) 0.249(7) Uani 1 1 d . . . . .
H51 H 0.613(2) 0.115(4) -0.014(3) 0.021(17) Uiso 1 1 d D . . . .
H50 H 0.060(4) 0.890(5) 0.495(5) 0.04(2) Uiso 1 1 d . . . . .
H52 H -0.049(3) 0.576(4) 0.069(3) 0.024(17) Uiso 1 1 d D . . . .
H53 H 0.596(4) 0.435(3) 0.208(4) 0.037 Uiso 1 1 d D U . . .
H54 H 0.606(4) 0.505(4) 0.258(3) 0.037 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1 C15 1.316(6) . ?
O2 C4 1.315(6) . ?
O3 C21 1.329(7) . ?
O4 C37 1.245(6) . ?
O5 C6 1.256(6) . ?
O6 N8 1.232(6) . ?
O7 C36 1.319(7) . ?
O8 N5 1.229(5) . ?
O9 N8 1.242(5) . ?
O10 C36 1.230(7) . ?
O11 C11 1.240(6) . ?
O12 C15 1.218(6) . ?
O13 C4 1.232(6) . ?
O14 C21 1.214(7) . ?
O15 N5 1.227(6) . ?
N2 C11 1.380(7) . ?
N2 C27 1.422(7) . ?
N3 C11 1.346(7) . ?
N4 C6 1.329(7) . ?
N5 C8 1.468(7) . ?
N6 C6 1.378(7) . ?
N6 C13 1.407(7) . ?
N7 C37 1.350(7) . ?
N7 C14 1.420(7) . ?
N8 C29 1.468(7) . ?
N10 C37 1.347(7) . ?
C3 C32 1.389(8) . ?
C3 C12 1.393(7) . ?
C4 C10 1.487(8) . ?
C5 C19 1.380(7) . ?
C5 C28 1.383(8) . ?
C7 C10 1.372(7) . ?
C7 C8 1.385(8) . ?
C8 C17 1.371(7) . ?
C9 C24 1.386(8) . ?
C9 C14 1.398(7) . ?
C10 C33 1.387(7) . ?
C12 C23 1.390(8) . ?
C13 C32 1.382(7) . ?
C13 C20 1.391(7) . ?
C14 C28 1.384(8) . ?
C15 C16 1.493(8) . ?
C16 C31 1.384(8) . ?
C16 C26 1.397(7) . ?
C17 C22 1.368(7) . ?
C18 C35 1.368(8) . ?
C18 C27 1.393(7) . ?
C19 C24 1.386(8) . ?
C20 C23 1.385(8) . ?
C21 C25 1.497(7) . ?
C22 C33 1.402(8) . ?
C22 C36 1.500(7) . ?
C25 C26 1.384(7) . ?
C25 C30 1.395(7) . ?
C27 C34 1.375(8) . ?
C29 C31 1.369(8) . ?
C29 C30 1.389(7) . ?
C34 C38 1.382(8) . ?
C35 C39 1.383(8) . ?
C38 C39 1.390(7) . ?
C100 C40 1.599(12) . ?
C40 O100 1.207(12) . ?
C40 C101 1.570(16) . ?

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
C11 N2 C27 128.7(5) . . ?
O15 N5 O8 123.8(5) . . ?
O15 N5 C8 118.3(5) . . ?
O8 N5 C8 117.8(5) . . ?
C6 N6 C13 129.8(6) . . ?
C37 N7 C14 127.9(5) . . ?
O6 N8 O9 122.9(5) . . ?
O6 N8 C29 119.8(5) . . ?
O9 N8 C29 117.3(5) . . ?
C32 C3 C12 121.6(6) . . ?
O13 C4 O2 125.1(6) . . ?
O13 C4 C10 122.0(6) . . ?
O2 C4 C10 112.9(5) . . ?
C19 C5 C28 120.6(6) . . ?
O5 C6 N4 123.1(5) . . ?
O5 C6 N6 120.8(6) . . ?
N4 C6 N6 116.1(6) . . ?
C10 C7 C8 120.6(5) . . ?
C17 C8 C7 120.7(6) . . ?
C17 C8 N5 120.4(6) . . ?
C7 C8 N5 118.9(5) . . ?
C24 C9 C14 119.6(6) . . ?
C7 C10 C33 118.7(6) . . ?
C7 C10 C4 119.6(5) . . ?
C33 C10 C4 121.6(6) . . ?
O11 C11 N3 123.4(5) . . ?
O11 C11 N2 121.8(6) . . ?
N3 C11 N2 114.8(5) . . ?
C23 C12 C3 117.8(6) . . ?
C32 C13 C20 120.4(5) . . ?
C32 C13 N6 123.7(5) . . ?
C20 C13 N6 116.0(5) . . ?
C28 C14 C9 118.8(6) . . ?
C28 C14 N7 117.0(5) . . ?
C9 C14 N7 124.1(6) . . ?
O12 C15 O1 124.7(6) . . ?
O12 C15 C16 122.4(6) . . ?
O1 C15 C16 112.9(5) . . ?
C31 C16 C26 119.4(5) . . ?
C31 C16 C15 118.8(5) . . ?
C26 C16 C15 121.9(5) . . ?
C22 C17 C8 119.6(6) . . ?
C35 C18 C27 119.2(6) . . ?
C5 C19 C24 118.8(6) . . ?
C23 C20 C13 119.4(6) . . ?
O14 C21 O3 125.4(5) . . ?
O14 C21 C25 122.4(6) . . ?
O3 C21 C25 112.1(6) . . ?
C17 C22 C33 119.9(5) . . ?
C17 C22 C36 122.8(6) . . ?
C33 C22 C36 117.3(5) . . ?
C20 C23 C12 121.6(5) . . ?
C19 C24 C9 121.2(5) . . ?
C26 C25 C30 120.3(5) . . ?
C26 C25 C21 117.7(6) . . ?
C30 C25 C21 122.0(5) . . ?
C25 C26 C16 120.5(5) . . ?
C34 C27 C18 120.5(6) . . ?
C34 C27 N2 124.1(5) . . ?
C18 C27 N2 115.4(5) . . ?
C5 C28 C14 120.9(5) . . ?
C31 C29 C30 122.6(6) . . ?
C31 C29 N8 119.3(5) . . ?
C30 C29 N8 118.1(5) . . ?
C29 C30 C25 117.8(5) . . ?
C29 C31 C16 119.4(5) . . ?
C13 C32 C3 119.3(5) . . ?
C10 C33 C22 120.3(6) . . ?
C27 C34 C38 119.0(6) . . ?
C18 C35 C39 121.8(6) . . ?
O10 C36 O7 124.2(5) . . ?
O10 C36 C22 122.1(6) . . ?
O7 C36 C22 113.7(6) . . ?
O4 C37 N10 122.0(6) . . ?
O4 C37 N7 122.1(6) . . ?
N10 C37 N7 115.9(5) . . ?
C34 C38 C39 121.7(6) . . ?
C35 C39 C38 117.7(6) . . ?
O100 C40 C101 123.1(13) . . ?
O100 C40 C100 119.5(15) . . ?
C101 C40 C100 115.3(11) . . ?

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
O1 H1 O4 0.82 1.70 2.506(6) 166.9 .
O2 H2 O17 0.82 1.81 2.626(7) 175.6 .
O3 H60 O11 0.82 1.76 2.576(5) 171.2 1_556
O7 H42 O5 0.82 1.76 2.572(5) 168.6 1_554
N3 H3A O14 0.86 2.07 2.894(5) 161.6 1_554
N3 H3B O9 0.86 2.18 3.038(6) 173.8 1_654
N4 H4A O10 0.86 2.04 2.862(6) 158.4 1_556
N4 H4B O8 0.86 2.16 3.021(6) 174.1 1_456
N10 H10A O12 0.86 2.13 2.966(7) 163.0 .
N10 H10B O13 0.86 2.37 3.113(6) 145.3 1_455
N10 H10B O17 0.86 2.58 3.189(6) 128.9 1_455
C9 H9 O4 0.93 2.23 2.829(7) 121.5 .
C32 H32 O5 0.93 2.26 2.860(7) 122.1 .
C34 H34 O11 0.93 2.26 2.866(7) 122.2 .
N2 H51 O6 0.865(19) 2.44(2) 3.280(6) 164(4) 1_654
N6 H50 O15 0.80(6) 2.45(6) 3.236(7) 164(6) 1_456
N7 H52 O13 0.857(19) 2.09(3) 2.914(6) 162(5) 1_455
O17 H53 O10 0.809(19) 2.24(5) 2.859(8) 133(6) 2_665
O17 H54 O100 0.814(19) 2.02(3) 2.795(10) 158(5) .

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM5
_database_code_depnum_ccdc_archive 'CCDC 1471786'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'tris(n-phenylurea) bis(5-nitroisophthalic acid) tetrahydrofuran solvate hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C8 H5 N1 O6), 3(C7 H8 N2 O1), H2 O1, C4 H8 O1'
_chemical_formula_sum            'C41 H44 N8 O17'
_chemical_formula_weight         920.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.3606(5)
_cell_length_b                   13.4644(6)
_cell_length_c                   14.3535(6)
_cell_angle_alpha                81.404(4)
_cell_angle_beta                 83.684(4)
_cell_angle_gamma                64.194(4)
_cell_volume                     2123.73(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    6760
_cell_measurement_theta_min      4.0980
_cell_measurement_theta_max      71.4980
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_min  0.67545
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            15570
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.769
_diffrn_reflns_theta_max         71.918
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8144
_reflns_number_gt                6568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXSL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+0.2666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8144
_refine_ls_number_parameters     760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 1.0301(18) -0.3177(18) 0.5377(15) 0.022(5) Uiso 1 1 d . . . . .
H40 H 0.179(2) 0.014(2) 0.1099(17) 0.034(6) Uiso 1 1 d . . . . .
H3 H 0.760(2) -0.0700(18) 0.3955(15) 0.027(5) Uiso 1 1 d . . . . .
H42 H -0.073(2) 0.2934(19) -0.0113(16) 0.029(5) Uiso 1 1 d . . . . .
H11 H 0.800(2) 0.494(2) 0.3695(19) 0.049(7) Uiso 1 1 d . . . . .
H2 H 1.074(2) -0.054(2) 0.4041(17) 0.039(6) Uiso 1 1 d . . . . .
H44 H 0.267(2) 0.2567(18) -0.0105(15) 0.028(5) Uiso 1 1 d . . . . .
H37 H 0.072(2) 0.164(2) 0.2955(16) 0.035(6) Uiso 1 1 d . . . . .
H39 H -0.094(2) 0.401(2) 0.1868(18) 0.035(6) Uiso 1 1 d . . . . .
H38 H -0.096(2) 0.295(2) 0.2397(19) 0.043(7) Uiso 1 1 d . . . . .
H9 H 0.892(2) 0.749(2) 0.2569(17) 0.039(6) Uiso 1 1 d . . . . .
H10 H 0.944(2) 0.570(2) 0.3337(17) 0.037(6) Uiso 1 1 d . . . . .
H36 H 0.292(2) 0.269(2) 0.2543(19) 0.047(7) Uiso 1 1 d . . . . .
H13 H 0.553(2) 0.782(2) 0.2354(18) 0.040(6) Uiso 1 1 d . . . . .
H7 H 0.604(2) 1.074(2) 0.1108(17) 0.034(6) Uiso 1 1 d . . . . .
H8 H 0.716(2) 1.090(2) 0.0986(17) 0.035(6) Uiso 1 1 d . . . . .
H17 H 0.181(3) 0.524(2) 0.280(2) 0.056(8) Uiso 1 1 d . . . . .
H16 H 0.305(2) 0.417(2) 0.4118(17) 0.037(6) Uiso 1 1 d . . . . .
H15 H 0.435(3) 0.273(2) 0.491(2) 0.048(7) Uiso 1 1 d . . . . .
H19 H 0.171(3) 0.825(2) 0.183(2) 0.052(7) Uiso 1 1 d . . . . .
H6 H 0.595(2) 0.926(2) 0.1775(18) 0.038(6) Uiso 1 1 d . . . . .
H14 H 0.565(3) 0.253(2) 0.4811(18) 0.040(6) Uiso 1 1 d . . . . .
H18 H 0.095(3) 0.692(2) 0.187(2) 0.054(8) Uiso 1 1 d . . . . .
H12 H 0.606(2) 0.602(2) 0.3197(18) 0.042(6) Uiso 1 1 d . . . . .
H20 H 0.331(3) 0.785(2) 0.280(2) 0.051(7) Uiso 1 1 d . . . . .
H32 H 0.491(3) 0.166(2) 0.298(2) 0.056(8) Uiso 1 1 d . . . . .
H5 H 0.736(3) 0.166(3) 0.279(2) 0.052(8) Uiso 1 1 d . . . . .
H21 H 0.416(3) 0.615(2) 0.3732(19) 0.049(7) Uiso 1 1 d . . . . .
H33 H 0.550(3) -0.016(3) 0.380(2) 0.065(9) Uiso 1 1 d . . . . .
H35 H 0.212(3) 0.012(2) 0.363(2) 0.057(8) Uiso 1 1 d . . . . .
H34 H 0.410(3) -0.089(3) 0.415(2) 0.074(10) Uiso 1 1 d . . . . .
H24 H 0.413(4) 0.417(4) 0.142(3) 0.111 Uiso 1 1 d . U . . .
H22 H 0.633(4) 0.349(4) 0.256(3) 0.111 Uiso 1 1 d . U . . .
H26 H 0.627(4) 0.322(4) -0.045(3) 0.111 Uiso 1 1 d . U . . .
H30 H 0.284(4) 0.478(4) 0.000(3) 0.111 Uiso 1 1 d . U . . .
H23 H 0.645(4) 0.308(4) 0.170(3) 0.111 Uiso 1 1 d . U . . .
H25 H 0.359(4) 0.338(4) 0.106(3) 0.111 Uiso 1 1 d . U . . .
H29 H 0.483(4) 0.434(4) -0.115(3) 0.111 Uiso 1 1 d . U . . .
H28 H 0.401(4) 0.379(4) -0.104(3) 0.111 Uiso 1 1 d . U . . .
H31 H 0.376(4) 0.533(4) 0.000(3) 0.111 Uiso 1 1 d . U . . .
H27 H 0.549(4) 0.240(4) -0.035(3) 0.111 Uiso 1 1 d . U . . .
H43 H -0.064(4) 0.520(4) -0.144(3) 0.111 Uiso 1 1 d . U . . .
H41 H -0.069(2) -0.034(2) 0.1368(19) 0.049(7) Uiso 1 1 d . . . . .
H4 H 1.304(3) -0.360(2) 0.574(2) 0.056(8) Uiso 1 1 d . . . . .
O11 O 0.92927(12) 0.11650(11) 0.31435(10) 0.0347(3) Uani 1 1 d . . . . .
O9 O 0.84693(13) -0.34966(12) 0.54538(11) 0.0404(3) Uani 1 1 d . . . . .
O8 O 0.70060(12) -0.21007(12) 0.47620(10) 0.0372(3) Uani 1 1 d . . . . .
O12 O 0.75635(12) 0.10366(12) 0.30679(10) 0.0349(3) Uani 1 1 d . . . . .
O10 O 1.25369(11) -0.18243(11) 0.49372(10) 0.0332(3) Uani 1 1 d . . . . .
C10 C 0.91057(16) -0.04500(15) 0.39038(12) 0.0277(4) Uani 1 1 d . . . . .
C15 C 0.88409(16) -0.20157(16) 0.47044(13) 0.0291(4) Uani 1 1 d . . . . .
O7 O 1.23478(12) -0.33705(11) 0.55606(10) 0.0348(3) Uani 1 1 d . . . . .
N2 N 0.80494(14) -0.25809(14) 0.49933(11) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.86634(16) 0.06657(15) 0.33285(13) 0.0296(4) Uani 1 1 d . . . . .
C16 C 0.83735(16) -0.09997(16) 0.41540(12) 0.0288(4) Uani 1 1 d . . . . .
C13 C 1.19648(16) -0.23736(15) 0.50945(13) 0.0288(4) Uani 1 1 d . . . . .
C12 C 1.07178(16) -0.19452(15) 0.47636(12) 0.0279(4) Uani 1 1 d . . . . .
C11 C 1.02651(16) -0.09269(15) 0.42124(13) 0.0282(4) Uani 1 1 d . . . . .
C14 C 0.99987(16) -0.25109(15) 0.50112(12) 0.0281(4) Uani 1 1 d . . . . .
O15 O 0.84931(12) 0.90975(11) 0.17206(10) 0.0343(3) Uani 1 1 d . . . . .
N4 N 0.67504(15) 0.88948(14) 0.19092(12) 0.0333(3) Uani 1 1 d . . . . .
N3 N 0.67874(16) 1.05054(14) 0.11653(13) 0.0360(4) Uani 1 1 d . . . . .
C37 C 0.83301(18) 0.71800(16) 0.26893(14) 0.0334(4) Uani 1 1 d . . . . .
C32 C 0.71637(17) 0.78067(16) 0.23961(13) 0.0318(4) Uani 1 1 d . . . . .
C31 C 0.73986(16) 0.94878(15) 0.16058(13) 0.0296(4) Uani 1 1 d . . . . .
C33 C 0.63222(19) 0.73646(19) 0.25887(16) 0.0406(5) Uani 1 1 d . . . . .
C36 C 0.8636(2) 0.61288(17) 0.31704(15) 0.0389(4) Uani 1 1 d . . . . .
C34 C 0.6652(2) 0.6309(2) 0.30684(18) 0.0471(5) Uani 1 1 d . . . . .
C35 C 0.7802(2) 0.56941(18) 0.33665(17) 0.0450(5) Uani 1 1 d . . . . .
O6 O -0.00859(12) -0.00267(11) 0.11798(10) 0.0355(3) Uani 1 1 d . . . . .
O3 O 0.12938(14) 0.44649(12) -0.08951(11) 0.0412(3) Uani 1 1 d . . . . .
C4 C 0.03965(16) 0.14448(15) 0.05458(12) 0.0284(4) Uani 1 1 d . . . . .
O4 O -0.04854(13) 0.44774(11) -0.10803(10) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.43576(14) 0.10247(16) 0.05745(14) 0.0550(4) Uani 1 1 d . . . . .
O1 O 0.39157(14) -0.02845(14) 0.12898(12) 0.0478(4) Uani 1 1 d . . . . .
C2 C 0.23953(16) 0.12687(16) 0.05539(13) 0.0311(4) Uani 1 1 d . . . . .
O5 O -0.15849(12) 0.15695(12) 0.06453(11) 0.0397(3) Uani 1 1 d . . . . .
N1 N 0.36377(15) 0.06187(15) 0.08298(12) 0.0378(4) Uani 1 1 d . . . . .
C6 C 0.09128(17) 0.29240(15) -0.02018(12) 0.0298(4) Uani 1 1 d . . . . .
C8 C 0.05973(18) 0.40386(16) -0.07612(13) 0.0320(4) Uani 1 1 d . . . . .
C3 C 0.15751(17) 0.08186(16) 0.08013(13) 0.0307(4) Uani 1 1 d . . . . .
C1 C -0.05332(16) 0.10095(15) 0.07957(13) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.20889(17) 0.23066(16) 0.00570(13) 0.0319(4) Uani 1 1 d . . . . .
C5 C 0.00657(16) 0.24983(15) 0.00481(12) 0.0287(4) Uani 1 1 d . . . . .
O14 O 0.55057(11) 0.41561(11) 0.37948(10) 0.0346(3) Uani 1 1 d . . . . .
C25 C 0.30646(16) 0.55213(16) 0.33408(14) 0.0319(4) Uani 1 1 d . . . . .
C24 C 0.46912(17) 0.38694(16) 0.41199(14) 0.0322(4) Uani 1 1 d . . . . .
N6 N 0.35281(14) 0.44831(14) 0.39097(13) 0.0357(4) Uani 1 1 d . . . . .
C26 C 0.35146(17) 0.63024(17) 0.33464(15) 0.0353(4) Uani 1 1 d . . . . .
C29 C 0.15990(19) 0.6787(2) 0.22490(16) 0.0447(5) Uani 1 1 d . . . . .
C30 C 0.20999(18) 0.57688(19) 0.27936(15) 0.0383(4) Uani 1 1 d . . . . .
N5 N 0.49242(17) 0.29315(16) 0.46926(16) 0.0469(5) Uani 1 1 d . . . . .
C28 C 0.2062(2) 0.75525(19) 0.22377(17) 0.0457(5) Uani 1 1 d . . . . .
C27 C 0.30204(19) 0.73081(18) 0.27841(18) 0.0432(5) Uani 1 1 d . . . . .
N8 N 0.11298(15) 0.20333(14) 0.28050(12) 0.0328(3) Uani 1 1 d . . . . .
O13 O 0.10906(14) 0.36655(12) 0.20834(12) 0.0430(4) Uani 1 1 d . . . . .
C17 C 0.23425(17) 0.14771(16) 0.30344(13) 0.0330(4) Uani 1 1 d . . . . .
N7 N -0.06052(16) 0.33946(15) 0.21982(13) 0.0373(4) Uani 1 1 d . . . . .
C18 C 0.05573(18) 0.30669(16) 0.23420(13) 0.0322(4) Uani 1 1 d . . . . .
C23 C 0.31798(19) 0.19250(18) 0.28312(16) 0.0391(4) Uani 1 1 d . . . . .
C20 C 0.3883(2) -0.0183(2) 0.3778(2) 0.0599(7) Uani 1 1 d . . . . .
C21 C 0.4710(2) 0.0255(2) 0.35797(19) 0.0527(6) Uani 1 1 d . . . . .
C22 C 0.4350(2) 0.1306(2) 0.31035(18) 0.0463(5) Uani 1 1 d . . . . .
C19 C 0.2719(2) 0.04109(19) 0.35104(18) 0.0472(5) Uani 1 1 d . . . . .
O16 O 0.53625(18) 0.31744(16) 0.07577(13) 0.0606(5) Uani 1 1 d . . . . .
C39 C 0.3652(3) 0.4547(3) 0.0040(3) 0.0841(11) Uani 1 1 d . . . . .
C38 C 0.4088(4) 0.3800(3) 0.0919(3) 0.0777(9) Uani 1 1 d . . . . .
C41 C 0.5535(4) 0.3068(2) -0.0222(2) 0.0661(8) Uani 1 1 d . . . . .
C40 C 0.4454(4) 0.3936(4) -0.0696(3) 0.0904(13) Uani 1 1 d . . . . .
O17 O 0.68002(16) 0.30340(14) 0.21983(12) 0.0480(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O11 C9 1.218(2) . ?
O9 N2 1.225(2) . ?
O8 N2 1.223(2) . ?
O12 C9 1.305(2) . ?
O10 C13 1.212(2) . ?
C10 C11 1.384(2) . ?
C10 C16 1.389(3) . ?
C10 C9 1.500(2) . ?
C15 C14 1.381(3) . ?
C15 C16 1.385(3) . ?
C15 N2 1.474(2) . ?
O7 C13 1.312(2) . ?
C13 C12 1.496(2) . ?
C12 C11 1.387(3) . ?
C12 C14 1.391(3) . ?
O15 C31 1.240(2) . ?
N4 C31 1.358(2) . ?
N4 C32 1.420(2) . ?
N3 C31 1.339(3) . ?
C37 C36 1.387(3) . ?
C37 C32 1.391(3) . ?
C32 C33 1.393(3) . ?
C33 C34 1.387(3) . ?
C36 C35 1.377(3) . ?
C34 C35 1.375(4) . ?
O6 C1 1.312(2) . ?
O3 C8 1.212(2) . ?
C4 C3 1.387(3) . ?
C4 C5 1.395(3) . ?
C4 C1 1.492(3) . ?
O4 C8 1.310(2) . ?
O2 N1 1.232(2) . ?
O1 N1 1.216(2) . ?
C2 C7 1.380(3) . ?
C2 C3 1.383(3) . ?
C2 N1 1.463(2) . ?
O5 C1 1.210(2) . ?
C6 C7 1.384(3) . ?
C6 C5 1.390(3) . ?
C6 C8 1.499(3) . ?
O14 C24 1.250(2) . ?
C25 C26 1.389(3) . ?
C25 C30 1.390(3) . ?
C25 N6 1.419(3) . ?
C24 N5 1.334(3) . ?
C24 N6 1.352(2) . ?
C26 C27 1.386(3) . ?
C29 C28 1.377(4) . ?
C29 C30 1.386(3) . ?
C28 C27 1.384(3) . ?
N8 C18 1.360(3) . ?
N8 C17 1.405(3) . ?
O13 C18 1.241(2) . ?
C17 C19 1.393(3) . ?
C17 C23 1.394(3) . ?
N7 C18 1.337(3) . ?
C23 C22 1.384(3) . ?
C20 C21 1.373(4) . ?
C20 C19 1.373(4) . ?
C21 C22 1.378(4) . ?
O16 C41 1.418(3) . ?
O16 C38 1.438(4) . ?
C39 C40 1.447(7) . ?
C39 C38 1.480(6) . ?
C41 C40 1.488(5) . ?

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
C11 C10 C16 119.36(16) . . ?
C11 C10 C9 118.86(16) . . ?
C16 C10 C9 121.76(16) . . ?
C14 C15 C16 123.31(16) . . ?
C14 C15 N2 118.58(16) . . ?
C16 C15 N2 118.09(16) . . ?
O8 N2 O9 123.88(15) . . ?
O8 N2 C15 117.73(15) . . ?
O9 N2 C15 118.39(15) . . ?
O11 C9 O12 124.53(17) . . ?
O11 C9 C10 121.51(16) . . ?
O12 C9 C10 113.95(16) . . ?
C15 C16 C10 118.22(16) . . ?
O10 C13 O7 124.93(17) . . ?
O10 C13 C12 121.42(16) . . ?
O7 C13 C12 113.65(15) . . ?
C11 C12 C14 119.65(16) . . ?
C11 C12 C13 117.75(16) . . ?
C14 C12 C13 122.57(16) . . ?
C10 C11 C12 121.62(16) . . ?
C15 C14 C12 117.83(16) . . ?
C31 N4 C32 127.80(16) . . ?
C36 C37 C32 119.61(18) . . ?
C37 C32 C33 119.33(19) . . ?
C37 C32 N4 124.32(17) . . ?
C33 C32 N4 116.35(18) . . ?
O15 C31 N3 122.45(17) . . ?
O15 C31 N4 121.62(17) . . ?
N3 C31 N4 115.92(17) . . ?
C34 C33 C32 119.9(2) . . ?
C35 C36 C37 121.1(2) . . ?
C35 C34 C33 120.8(2) . . ?
C34 C35 C36 119.3(2) . . ?
C3 C4 C5 120.00(17) . . ?
C3 C4 C1 120.96(16) . . ?
C5 C4 C1 119.04(16) . . ?
C7 C2 C3 122.63(17) . . ?
C7 C2 N1 118.69(17) . . ?
C3 C2 N1 118.68(17) . . ?
O1 N1 O2 123.15(18) . . ?
O1 N1 C2 119.56(17) . . ?
O2 N1 C2 117.30(17) . . ?
C7 C6 C5 119.86(17) . . ?
C7 C6 C8 118.27(17) . . ?
C5 C6 C8 121.87(17) . . ?
O3 C8 O4 124.96(18) . . ?
O3 C8 C6 122.09(18) . . ?
O4 C8 C6 112.95(16) . . ?
C2 C3 C4 118.32(17) . . ?
O5 C1 O6 124.68(17) . . ?
O5 C1 C4 122.28(17) . . ?
O6 C1 C4 113.04(15) . . ?
C2 C7 C6 118.75(17) . . ?
C6 C5 C4 120.44(17) . . ?
C26 C25 C30 119.71(19) . . ?
C26 C25 N6 121.99(17) . . ?
C30 C25 N6 118.25(18) . . ?
O14 C24 N5 121.65(18) . . ?
O14 C24 N6 122.27(17) . . ?
N5 C24 N6 116.08(17) . . ?
C24 N6 C25 126.03(16) . . ?
C27 C26 C25 119.62(19) . . ?
C28 C29 C30 120.3(2) . . ?
C29 C30 C25 120.0(2) . . ?
C29 C28 C27 119.7(2) . . ?
C28 C27 C26 120.6(2) . . ?
C18 N8 C17 127.97(17) . . ?
C19 C17 C23 118.34(19) . . ?
C19 C17 N8 117.08(18) . . ?
C23 C17 N8 124.57(18) . . ?
O13 C18 N7 122.76(18) . . ?
O13 C18 N8 121.28(18) . . ?
N7 C18 N8 115.96(17) . . ?
C22 C23 C17 119.6(2) . . ?
C21 C20 C19 121.0(2) . . ?
C20 C21 C22 118.6(2) . . ?
C21 C22 C23 121.5(2) . . ?
C20 C19 C17 120.9(2) . . ?
C41 O16 C38 105.3(3) . . ?
C40 C39 C38 104.0(3) . . ?
O16 C38 C39 106.3(3) . . ?
O16 C41 C40 108.1(3) . . ?
C39 C40 C41 106.3(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
N8 H37 O11 0.87(3) 2.10(3) 2.942(2) 161(2) 1_455
N7 H39 O3 0.84(3) 2.21(3) 3.022(2) 164(2) 2_565
N7 H38 O11 0.89(3) 2.38(3) 3.153(2) 146(2) 1_455
C37 H9 O15 0.97(3) 2.20(3) 2.821(2) 121.1(19) .
C23 H36 O13 0.98(3) 2.18(3) 2.811(3) 121(2) .
N3 H7 O2 0.84(3) 2.15(3) 2.964(2) 161(2) 1_565
N3 H8 O5 0.85(3) 2.09(3) 2.918(2) 168(2) 1_665
N6 H16 O9 0.88(3) 2.40(3) 3.270(2) 172(2) 2_656
N5 H15 O8 0.88(3) 2.17(3) 3.034(2) 170(3) 2_656
N4 H6 O1 0.92(3) 2.47(3) 3.363(2) 164(2) 1_565
N5 H14 O10 0.84(3) 2.07(3) 2.900(2) 169(2) 2_756
O12 H5 O17 0.82(3) 1.78(3) 2.594(2) 176(3) .
O17 H22 O14 0.84(5) 2.07(5) 2.867(2) 160(4) .
C39 H30 O3 0.92(5) 2.62(5) 3.391(3) 142(4) .
O17 H23 O16 0.86(5) 1.96(5) 2.805(3) 167(4) .
O4 H43 O13 0.98(5) 1.56(4) 2.5333(19) 170(4) 2_565
O6 H41 O15 1.00(3) 1.51(3) 2.5115(19) 174(3) 1_445
O7 H4 O14 0.83(3) 1.78(3) 2.6112(19) 175(3) 2_756

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM6
_database_code_depnum_ccdc_archive 'CCDC 1471787'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Hepta(n-phenylurea) tetra(5-nitroisophthalic acid) ethyl acetate solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H5 N1 O6), 3(C7 H8 N2 O1), C4 H8 O2'
_chemical_formula_sum            'C41 H42 N8 O17'
_chemical_formula_weight         918.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8732(4)
_cell_length_b                   10.9970(3)
_cell_length_c                   20.4449(6)
_cell_angle_alpha                80.035(2)
_cell_angle_beta                 89.288(3)
_cell_angle_gamma                77.290(3)
_cell_volume                     2131.99(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    6330
_cell_measurement_theta_min      4.1950
_cell_measurement_theta_max      71.7070
_exptl_crystal_description       'hexagonal blocks'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_min  0.68908
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            16547
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.393
_diffrn_reflns_theta_max         71.995
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8157
_reflns_number_gt                6377
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8157
_refine_ls_number_parameters     763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H7 H 0.157(3) 1.015(2) 0.5480(12) 0.028(6) Uiso 1 1 d . . . . .
H11 H 0.176(2) 0.536(2) 0.0442(11) 0.026(6) Uiso 1 1 d . . . . .
H12 H 0.320(2) 0.160(2) 0.0660(11) 0.025(6) Uiso 1 1 d . . . . .
H16 H 0.448(2) 0.598(2) 0.0367(11) 0.024(5) Uiso 1 1 d . . . . .
H9 H 0.303(3) 0.636(2) 0.5818(12) 0.034(6) Uiso 1 1 d . . . . .
H15 H 0.366(3) 0.982(3) 0.0122(13) 0.039(7) Uiso 1 1 d . . . . .
H2 H 0.217(3) 0.682(2) 0.2956(13) 0.034(6) Uiso 1 1 d . . . . .
H5 H 0.014(3) 1.116(2) 0.2456(13) 0.032(6) Uiso 1 1 d . . . . .
H4 H 0.122(3) 0.912(2) 0.0967(12) 0.031(6) Uiso 1 1 d . . . . .
H6 H -0.067(3) 1.302(2) 0.1662(13) 0.036(7) Uiso 1 1 d . . . . .
H10 H 0.324(3) 0.339(2) 0.2240(14) 0.039(7) Uiso 1 1 d . . . . .
H1 H 0.210(3) 0.724(2) 0.3611(14) 0.030(6) Uiso 1 1 d . . . . .
H8 H 0.291(2) 0.830(2) 0.7340(12) 0.024(5) Uiso 1 1 d . . . . .
H17 H 0.391(3) 0.610(2) -0.0752(13) 0.036(6) Uiso 1 1 d . . . . .
H3 H 0.147(3) 0.820(3) 0.2057(13) 0.038(7) Uiso 1 1 d . . . . .
H14 H 0.479(3) 0.809(2) 0.2158(12) 0.028(6) Uiso 1 1 d . . . . .
H13 H 0.531(3) 0.669(2) 0.2448(13) 0.033(6) Uiso 1 1 d . . . . .
H31 H -0.059(3) 1.289(2) 0.0504(13) 0.038(7) Uiso 1 1 d . . . . .
H26 H -0.026(3) 0.623(2) -0.2560(14) 0.039(7) Uiso 1 1 d . . . . .
H29 H 0.416(3) 0.872(2) 0.1092(12) 0.032(6) Uiso 1 1 d . . . . .
H30 H 0.033(3) 1.098(2) 0.0168(14) 0.040(7) Uiso 1 1 d . . . . .
H24 H -0.103(3) 0.809(2) -0.4521(13) 0.039(7) Uiso 1 1 d . . . . .
H28 H 0.307(2) 0.999(2) -0.1008(11) 0.024(5) Uiso 1 1 d . . . . .
H22 H 0.083(3) 0.425(3) -0.4060(14) 0.045(7) Uiso 1 1 d . . . . .
H18 H 0.176(3) 0.238(3) -0.1418(15) 0.043(8) Uiso 1 1 d . . . . .
H25 H -0.114(3) 0.812(2) -0.3385(12) 0.032(6) Uiso 1 1 d . . . . .
H21 H 0.099(3) 0.326(2) -0.2981(13) 0.034(6) Uiso 1 1 d . . . . .
H19 H 0.169(3) 0.197(3) -0.2072(14) 0.043(7) Uiso 1 1 d . . . . .
H27 H 0.323(3) 0.809(2) -0.1458(13) 0.032(6) Uiso 1 1 d . . . . .
H23 H -0.005(3) 0.613(3) -0.4863(16) 0.052(8) Uiso 1 1 d . . . . .
H20 H 0.130(3) 0.457(3) -0.1088(16) 0.055(9) Uiso 1 1 d . . . . .
H38 H 0.654(3) 0.708(2) 0.4074(13) 0.037(7) Uiso 1 1 d . . . . .
H34 H 0.535(4) 0.613(3) 0.5274(17) 0.068(10) Uiso 1 1 d . . . . .
H36 H 0.663(3) 0.536(3) 0.4949(14) 0.046(7) Uiso 1 1 d . . . . .
H37 H 0.504(3) 0.677(3) 0.4135(14) 0.046(8) Uiso 1 1 d . . . . .
H39 H 0.378(4) 1.035(3) 0.4537(17) 0.061(9) Uiso 1 1 d . . . . .
H41 H 0.382(4) 1.103(3) 0.3771(18) 0.073(11) Uiso 1 1 d . . . . .
H32 H 0.448(4) 0.039(3) 0.2786(17) 0.064(10) Uiso 1 1 d . . . . .
H35 H 0.685(4) 0.656(3) 0.5210(18) 0.076(11) Uiso 1 1 d . . . . .
H33 H 0.420(4) 0.527(3) 0.8004(19) 0.081(11) Uiso 1 1 d . . . . .
H40 H 0.499(4) 1.082(3) 0.4211(19) 0.080(12) Uiso 1 1 d . . . . .
H42 H 0.140(4) 0.930(3) 0.3951(17) 0.064(10) Uiso 1 1 d . . . . .
O5 O 0.14663(17) 0.93328(12) 0.44687(7) 0.0311(3) Uani 1 1 d . . . . .
O1 O 0.14480(18) 1.15914(12) 0.63051(8) 0.0377(4) Uani 1 1 d . . . . .
O6 O 0.23330(18) 0.72378(12) 0.46184(7) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.20434(19) 1.05572(14) 0.72940(8) 0.0391(4) Uani 1 1 d . . . . .
O3 O 0.3915(2) 0.49501(13) 0.68954(8) 0.0414(4) Uani 1 1 d . . . . .
O4 O 0.38072(18) 0.60814(12) 0.77139(7) 0.0345(4) Uani 1 1 d . . . . .
O7 O 0.11980(17) 0.94976(12) 0.32277(7) 0.0303(3) Uani 1 1 d . . . . .
C12 C 0.2722(2) 0.83052(17) 0.68882(10) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.2261(2) 0.82796(16) 0.55435(9) 0.0234(4) Uani 1 1 d . . . . .
C2 C 0.0765(2) 0.99828(16) 0.17845(10) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.2803(2) 0.71657(16) 0.59785(10) 0.0244(4) Uani 1 1 d . . . . .
N3 N 0.12772(19) 0.88349(14) 0.22270(8) 0.0272(4) Uani 1 1 d . . . . .
C10 C 0.1932(2) 0.94236(16) 0.57786(10) 0.0235(4) Uani 1 1 d . . . . .
N4 N 0.1975(2) 0.74205(15) 0.31820(9) 0.0355(4) Uani 1 1 d . . . . .
C5 C -0.0236(2) 1.21482(18) 0.08415(11) 0.0293(4) Uani 1 1 d . . . . .
C7 C 0.0808(2) 0.99279(17) 0.11109(10) 0.0271(4) Uani 1 1 d . . . . .
N2 N 0.18606(18) 1.06047(14) 0.66972(9) 0.0282(4) Uani 1 1 d . . . . .
C13 C 0.3039(2) 0.71699(16) 0.66460(10) 0.0241(4) Uani 1 1 d . . . . .
C8 C 0.2013(2) 0.82260(16) 0.48303(10) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.0203(2) 1.11363(17) 0.19897(11) 0.0269(4) Uani 1 1 d . . . . .
C23 C 0.3634(2) 0.59446(17) 0.71009(10) 0.0279(4) Uani 1 1 d . . . . .
C4 C -0.0291(2) 1.22049(17) 0.15130(11) 0.0292(4) Uani 1 1 d . . . . .
C11 C 0.2184(2) 0.94019(16) 0.64415(10) 0.0234(4) Uani 1 1 d . . . . .
C6 C 0.0317(2) 1.10042(18) 0.06427(10) 0.0293(4) Uani 1 1 d . . . . .
C1 C 0.1477(2) 0.86236(16) 0.28945(10) 0.0260(4) Uani 1 1 d . . . . .
O12 O 0.16695(19) 0.66861(13) 0.12836(9) 0.0418(4) Uani 1 1 d . . . . .
O15 O 0.41187(16) 0.00571(12) 0.17368(7) 0.0311(3) Uani 1 1 d . . . . .
O9 O 0.15336(18) 0.45814(12) -0.06131(7) 0.0344(4) Uani 1 1 d . . . . .
N6 N 0.0799(2) 0.39365(14) -0.28127(9) 0.0288(4) Uani 1 1 d . . . . .
O10 O 0.23555(18) 0.24892(12) -0.04986(7) 0.0340(3) Uani 1 1 d . . . . .
O13 O 0.2419(2) 0.55865(14) 0.22407(8) 0.0418(4) Uani 1 1 d . . . . .
C17 C 0.2134(2) 0.45944(16) 0.06954(10) 0.0243(4) Uani 1 1 d . . . . .
O11 O 0.09010(18) 0.46590(12) -0.18393(7) 0.0340(3) Uani 1 1 d . . . . .
C35 C -0.0701(2) 0.72633(19) -0.41920(11) 0.0334(5) Uani 1 1 d . . . . .
O14 O 0.4226(2) 0.11587(14) 0.25430(8) 0.0453(4) Uani 1 1 d . . . . .
C16 C 0.2432(2) 0.34777(16) 0.04339(10) 0.0236(4) Uani 1 1 d . . . . .
C22 C 0.3915(2) 0.10553(17) 0.19331(10) 0.0263(4) Uani 1 1 d . . . . .
C20 C 0.3297(2) 0.22924(16) 0.15092(10) 0.0227(4) Uani 1 1 d . . . . .
C19 C 0.3016(2) 0.33980(17) 0.17785(10) 0.0254(4) Uani 1 1 d . . . . .
C33 C -0.0281(2) 0.62314(18) -0.30471(11) 0.0293(4) Uani 1 1 d . . . . .
N5 N 0.1525(2) 0.25595(15) -0.18480(10) 0.0357(4) Uani 1 1 d . . . . .
C32 C 0.0298(2) 0.50837(17) -0.32510(10) 0.0267(4) Uani 1 1 d . . . . .
C18 C 0.2447(2) 0.45163(16) 0.13606(10) 0.0251(4) Uani 1 1 d . . . . .
N1 N 0.21514(19) 0.56827(15) 0.16456(9) 0.0311(4) Uani 1 1 d . . . . .
C37 C 0.0366(3) 0.50422(19) -0.39264(11) 0.0337(5) Uani 1 1 d . . . . .
C21 C 0.3004(2) 0.23387(16) 0.08433(10) 0.0233(4) Uani 1 1 d . . . . .
C31 C 0.1080(2) 0.37600(17) -0.21491(10) 0.0270(4) Uani 1 1 d . . . . .
C34 C -0.0772(2) 0.73076(17) -0.35191(11) 0.0321(4) Uani 1 1 d . . . . .
C36 C -0.0124(3) 0.6125(2) -0.43909(11) 0.0363(5) Uani 1 1 d . . . . .
C15 C 0.2104(2) 0.34659(16) -0.02747(10) 0.0263(4) Uani 1 1 d . . . . .
N7 N 0.43684(19) 0.79464(14) 0.10118(8) 0.0278(4) Uani 1 1 d . . . . .
O8 O 0.51683(17) 0.58520(12) 0.14338(7) 0.0327(3) Uani 1 1 d . . . . .
C26 C 0.3693(2) 0.90786(17) -0.00796(11) 0.0291(4) Uani 1 1 d . . . . .
C30 C 0.4177(2) 0.68011(17) 0.00835(10) 0.0274(4) Uani 1 1 d . . . . .
C25 C 0.4095(2) 0.79146(16) 0.03424(10) 0.0249(4) Uani 1 1 d . . . . .
C29 C 0.3484(2) 0.8034(2) -0.09995(11) 0.0317(4) Uani 1 1 d . . . . .
N8 N 0.4973(2) 0.73024(15) 0.21133(9) 0.0356(4) Uani 1 1 d . . . . .
C28 C 0.3859(2) 0.68837(18) -0.05820(11) 0.0301(4) Uani 1 1 d . . . . .
C24 C 0.4860(2) 0.69792(17) 0.15152(10) 0.0264(4) Uani 1 1 d . . . . .
C27 C 0.3385(2) 0.91424(19) -0.07450(11) 0.0321(4) Uani 1 1 d . . . . .
O16 O 0.5100(2) 0.90292(14) 0.33795(8) 0.0425(4) Uani 1 1 d . . . . .
O17 O 0.51762(17) 0.82890(13) 0.44663(8) 0.0357(4) Uani 1 1 d . . . . .
C40 C 0.5779(3) 0.7014(2) 0.43378(13) 0.0397(5) Uani 1 1 d . . . . .
C39 C 0.4275(3) 1.04699(19) 0.41322(12) 0.0355(5) Uani 1 1 d . . . . .
C38 C 0.4881(2) 0.92042(18) 0.39448(11) 0.0305(4) Uani 1 1 d . . . . .
C41 C 0.6186(3) 0.6190(2) 0.49949(14) 0.0430(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O5 C8 1.315(2) . ?
O1 N2 1.224(2) . ?
O6 C8 1.215(2) . ?
O2 N2 1.226(2) . ?
O3 C23 1.213(2) . ?
O4 C23 1.306(2) . ?
O7 C1 1.253(2) . ?
C12 C11 1.386(3) . ?
C12 C13 1.393(2) . ?
C9 C14 1.387(3) . ?
C9 C10 1.394(2) . ?
C9 C8 1.495(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.401(2) . ?
C2 N3 1.415(2) . ?
C14 C13 1.388(3) . ?
N3 C1 1.353(3) . ?
C10 C11 1.376(3) . ?
N4 C1 1.338(2) . ?
C5 C6 1.384(3) . ?
C5 C4 1.385(3) . ?
C7 C6 1.385(3) . ?
N2 C11 1.474(2) . ?
C13 C23 1.502(2) . ?
C3 C4 1.390(3) . ?
O12 N1 1.219(2) . ?
O15 C22 1.208(2) . ?
O9 C15 1.309(2) . ?
N6 C31 1.360(3) . ?
N6 C32 1.409(2) . ?
O10 C15 1.214(2) . ?
O13 N1 1.230(2) . ?
C17 C18 1.382(3) . ?
C17 C16 1.395(2) . ?
O11 C31 1.244(2) . ?
C35 C36 1.384(3) . ?
C35 C34 1.385(3) . ?
O14 C22 1.318(3) . ?
C16 C21 1.388(3) . ?
C16 C15 1.491(3) . ?
C22 C20 1.488(2) . ?
C20 C21 1.385(3) . ?
C20 C19 1.392(2) . ?
C19 C18 1.379(3) . ?
C33 C34 1.390(3) . ?
C33 C32 1.397(3) . ?
N5 C31 1.336(2) . ?
C32 C37 1.390(3) . ?
C18 N1 1.470(2) . ?
C37 C36 1.386(3) . ?
N7 C24 1.354(3) . ?
N7 C25 1.406(3) . ?
O8 C24 1.249(2) . ?
C26 C27 1.384(3) . ?
C26 C25 1.394(3) . ?
C30 C28 1.383(3) . ?
C30 C25 1.402(3) . ?
C29 C28 1.376(3) . ?
C29 C27 1.390(3) . ?
N8 C24 1.343(3) . ?
O16 C38 1.213(3) . ?
O17 C38 1.320(2) . ?
O17 C40 1.465(2) . ?
C40 C41 1.490(3) . ?
C39 C38 1.502(3) . ?

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
C11 C12 C13 117.70(18) . . ?
C14 C9 C10 119.77(18) . . ?
C14 C9 C8 119.11(16) . . ?
C10 C9 C8 121.11(17) . . ?
C7 C2 C3 119.43(17) . . ?
C7 C2 N3 116.72(16) . . ?
C3 C2 N3 123.84(18) . . ?
C9 C14 C13 121.06(16) . . ?
C1 N3 C2 129.69(16) . . ?
C11 C10 C9 117.98(16) . . ?
C6 C5 C4 119.28(18) . . ?
C6 C7 C2 120.61(18) . . ?
O1 N2 O2 123.67(16) . . ?
O1 N2 C11 118.70(17) . . ?
O2 N2 C11 117.62(16) . . ?
C14 C13 C12 119.89(17) . . ?
C14 C13 C23 119.49(16) . . ?
C12 C13 C23 120.62(18) . . ?
O6 C8 O5 124.78(18) . . ?
O6 C8 C9 121.43(17) . . ?
O5 C8 C9 113.77(15) . . ?
C4 C3 C2 119.16(19) . . ?
O3 C23 O4 125.51(18) . . ?
O3 C23 C13 121.20(18) . . ?
O4 C23 C13 113.29(16) . . ?
C5 C4 C3 121.23(18) . . ?
C10 C11 C12 123.59(16) . . ?
C10 C11 N2 118.75(16) . . ?
C12 C11 N2 117.67(17) . . ?
C5 C6 C7 120.29(19) . . ?
O7 C1 N4 121.61(19) . . ?
O7 C1 N3 122.24(17) . . ?
N4 C1 N3 116.14(17) . . ?
C31 N6 C32 128.20(16) . . ?
C18 C17 C16 117.77(17) . . ?
C36 C35 C34 118.91(19) . . ?
C21 C16 C17 119.74(18) . . ?
C21 C16 C15 118.67(16) . . ?
C17 C16 C15 121.55(17) . . ?
O15 C22 O14 123.37(18) . . ?
O15 C22 C20 123.40(18) . . ?
O14 C22 C20 113.22(16) . . ?
C21 C20 C19 120.09(17) . . ?
C21 C20 C22 119.59(16) . . ?
C19 C20 C22 120.33(18) . . ?
C18 C19 C20 117.68(19) . . ?
C34 C33 C32 119.78(19) . . ?
C37 C32 C33 119.02(18) . . ?
C37 C32 N6 116.83(17) . . ?
C33 C32 N6 124.14(18) . . ?
C19 C18 C17 123.69(17) . . ?
C19 C18 N1 117.62(18) . . ?
C17 C18 N1 118.69(17) . . ?
O12 N1 O13 123.67(16) . . ?
O12 N1 C18 118.83(18) . . ?
O13 N1 C18 117.49(17) . . ?
C36 C37 C32 120.50(19) . . ?
C20 C21 C16 121.02(16) . . ?
O11 C31 N5 122.10(19) . . ?
O11 C31 N6 122.00(17) . . ?
N5 C31 N6 115.88(17) . . ?
C35 C34 C33 121.05(19) . . ?
C35 C36 C37 120.7(2) . . ?
O10 C15 O9 124.86(19) . . ?
O10 C15 C16 121.27(17) . . ?
O9 C15 C16 113.87(16) . . ?
C24 N7 C25 129.43(16) . . ?
C27 C26 C25 120.88(18) . . ?
C28 C30 C25 119.35(17) . . ?
C26 C25 C30 118.95(19) . . ?
C26 C25 N7 116.73(17) . . ?
C30 C25 N7 124.31(17) . . ?
C28 C29 C27 119.4(2) . . ?
C29 C28 C30 121.55(18) . . ?
O8 C24 N8 121.82(18) . . ?
O8 C24 N7 122.31(19) . . ?
N8 C24 N7 115.86(16) . . ?
C26 C27 C29 119.82(18) . . ?
C38 O17 C40 116.96(17) . . ?
O17 C40 C41 106.99(19) . . ?
O16 C38 O17 122.97(19) . . ?
O16 C38 C39 124.43(19) . . ?
O17 C38 C39 112.58(19) . . ?

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
C30 H16 O8 0.97(2) 2.27(2) 2.879(3) 120.0(17) .
N4 H2 O13 0.86(3) 2.14(3) 2.983(2) 169(2) .
C3 H5 O7 0.96(3) 2.26(2) 2.885(3) 121.5(19) .
C7 H4 O12 0.99(2) 2.58(2) 3.434(2) 144.9(19) .
N4 H1 O6 0.87(3) 2.07(3) 2.929(2) 168(2) .
N3 H3 O12 0.82(3) 2.46(3) 3.257(2) 164(2) .
N8 H14 O15 0.87(2) 2.14(2) 2.927(2) 150(2) 1_565
N8 H13 O3 0.88(3) 2.06(3) 2.927(2) 169(2) 2_666
C33 H26 O11 1.00(3) 2.19(3) 2.856(3) 123(2) .
N7 H29 O15 0.87(3) 2.13(3) 2.928(2) 152(2) 1_565
N5 H18 O10 0.89(3) 2.01(3) 2.871(2) 163(2) .
N6 H21 O1 0.85(3) 2.50(3) 3.342(2) 168(2) 1_544
N5 H19 O2 0.85(3) 2.16(3) 3.001(2) 176(3) 1_544
O9 H20 O11 1.00(3) 1.57(3) 2.574(2) 176(3) .
C39 H41 O14 0.93(4) 2.52(4) 3.205(3) 131(3) 1_565
O14 H32 O16 0.89(3) 1.75(3) 2.630(2) 168(3) 1_545
O4 H33 O8 0.98(4) 1.56(4) 2.5288(19) 169(4) 2_666
O5 H42 O7 1.07(3) 1.47(3) 2.525(2) 169(3) .
O7 H42 O6 1.47(3) 2.42(3) 3.453(2) 123.2(19) .

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM7
_database_code_depnum_ccdc_archive 'CCDC 1471788'
_audit_update_record             
;
2016-06-09 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014

# start Validation Reply Form
_vrf_DIFMN02_shelx               
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: There is disordered solvent present in channels of the structure
whose structure could not be fully resolved. 
;
_vrf_PLAT043_shelx               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 24.11 Check
RESPONSE: This difference is due to the molecular formula for the disordered solvent guests
being included in the SFAC values when it was not possible to fully resolve their structure
in the model. The solvent hydrogen atoms are missing from the model and the methanol solvent
oxygen atom has been modelled as a carbon atom for a stable structure refinement.  
;
_vrf_PLAT098_shelx               
;
PROBLEM: Large Reported Min. (Negative) Residual Density -0.98 eA-3
RESPONSE: The structure of the disordered solvent could not be fully resolved. The methanol
solvent oxygen atom has been modelled as a carbon atom for a stable structure refinement.
;
_vrf_PLAT417_shelx               
;
PROBLEM: Short Inter D-H..H-D H1 .. H1 .. 2.00 Ang.
RESPONSE: H1 is in a centrosymmetric carboxylic acid dimer. 
;
# end Validation Reply Form

_chemical_name_systematic        
'bis(n-phenylurea) bis(5-nitroisophthalic acid) tetrahydrofuran methanol solvate '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C8 H5 N O6, C7 H8 N2 O, 0.5(C4 O1 H8), C1 O1 H4'
_chemical_formula_sum            'C18 H21 N3 O8.50'
_chemical_formula_weight         415.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9483(8)
_cell_length_b                   9.9564(8)
_cell_length_c                   10.6641(7)
_cell_angle_alpha                66.488(7)
_cell_angle_beta                 75.790(7)
_cell_angle_gamma                71.335(7)
_cell_volume                     909.16(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.00(14)
_cell_measurement_reflns_used    3266
_cell_measurement_theta_min      4.5470
_cell_measurement_theta_max      74.6230

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_min  0.96832
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3620
_diffrn_reflns_number            6117
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.564
_diffrn_reflns_theta_max         75.016
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3565
_reflns_number_gt                3029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

Aromatic hydrogen atoms were fixed in riding positions for 5-nitroisophthalic acid 
and n-phenylurea using HFIX 43.

There is disordered solvent present in channels which sits on an inversion centre. 
Half of a molecule of THF and one molecule of methanol have been modelled 
(these were the crystallisation solvents). In the methanol solvent, to achieve a stable
refinement, the methanol oxygen atom is modelled as a carbon atom.

 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²+0.5377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.2040
_refine_ls_wR_factor_gt          0.1914
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C102 C 0.4861(10) 0.5590(7) 0.0877(7) 0.0498(13) Uiso 0.5 1 d . . P . .
C103 C 0.3596(8) 0.5155(7) 0.1046(7) 0.0507(14) Uiso 0.5 1 d . . P . .
C106 C 0.4239(8) 0.5250(6) 0.1085(6) 0.0427(12) Uiso 0.5 1 d . . P . .
O107 O 0.5845(10) 0.5409(9) -0.0212(9) 0.103(2) Uiso 0.5 1 d . . P . .
C104 C 0.5520(8) 0.5648(6) 0.0875(6) 0.0445(12) Uiso 0.5 1 d . . P . .
C101 C 0.6593(7) 0.5462(6) -0.0190(6) 0.0936(15) Uiso 1 1 d . . . . .
C105 C 0.8019(9) 0.5869(10) -0.0373(9) 0.139(2) Uiso 1 1 d . . . . .
H6 H 0.947(3) 0.779(3) 0.076(4) 0.041(8) Uiso 1 1 d . . . . .
H7 H 0.822(3) 0.761(3) 0.188(3) 0.030(6) Uiso 1 1 d . . . . .
H8 H 1.123(4) 0.846(4) 0.079(4) 0.061(10) Uiso 1 1 d . . . . .
H5 H 0.261(5) 0.172(5) 0.599(5) 0.075(12) Uiso 1 1 d . . . . .
H1 H 0.909(6) 0.499(7) 0.566(6) 0.13(2) Uiso 1 1 d . . . . .
O6 O 0.83077(18) 0.4613(2) 0.56931(17) 0.0360(4) Uani 1 1 d . . . . .
O2 O 0.35296(18) 0.1738(2) 0.54871(18) 0.0382(4) Uani 1 1 d . . . . .
O7 O 0.89789(17) 0.8468(2) 0.33432(16) 0.0352(4) Uani 1 1 d . . . . .
O3 O 0.68465(19) 0.1342(2) 0.15670(18) 0.0401(4) Uani 1 1 d . . . . .
O1 O 0.37033(18) 0.2957(2) 0.67887(18) 0.0385(4) Uani 1 1 d . . . . .
O5 O 0.98528(17) 0.4299(2) 0.38536(17) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.7627(2) 0.1937(2) 0.1767(2) 0.0339(5) Uani 1 1 d . . . . .
N2 N 1.0840(2) 0.8733(2) 0.16028(19) 0.0317(4) Uani 1 1 d . . . . .
O4 O 0.87323(19) 0.2183(3) 0.09955(18) 0.0480(5) Uani 1 1 d . . . . .
C10 C 0.7724(2) 0.3508(3) 0.4372(2) 0.0295(5) Uani 1 1 d . . . . .
C1 C 1.1600(2) 0.9400(3) 0.2053(2) 0.0336(5) Uani 1 1 d . . . . .
C8 C 0.7233(2) 0.2404(3) 0.2983(2) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.8701(2) 0.4188(2) 0.4656(2) 0.0280(5) Uani 1 1 d . . . . .
N3 N 0.9018(2) 0.7837(3) 0.1521(2) 0.0357(5) Uani 1 1 d . . . . .
C2 C 1.1063(2) 0.9984(3) 0.3116(2) 0.0349(5) Uani 1 1 d . . . . .
H13 H 1.0168 0.9899 0.3619 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5973(2) 0.2175(3) 0.3817(2) 0.0338(5) Uani 1 1 d . . . . .
H4 H 0.5407 0.1709 0.3632 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9578(2) 0.8350(2) 0.2211(2) 0.0279(5) Uani 1 1 d . . . . .
C11 C 0.6446(2) 0.3325(3) 0.5219(2) 0.0304(5) Uani 1 1 d . . . . .
H3 H 0.6174 0.3648 0.5971 0.036 Uiso 1 1 calc R U . . .
C9 C 0.8136(2) 0.3051(3) 0.3228(2) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.8988 0.3177 0.2650 0.037 Uiso 1 1 calc R U . . .
C14 C 0.4172(2) 0.2467(3) 0.5846(2) 0.0324(5) Uani 1 1 d . . . . .
C5 C 1.3764(4) 1.0178(6) 0.1667(3) 0.0703(11) Uani 1 1 d . . . . .
H11 H 1.4676 1.0227 0.1194 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5564(2) 0.2657(3) 0.4947(2) 0.0326(5) Uani 1 1 d . . . . .
C20 C 1.2962(3) 0.9488(4) 0.1339(3) 0.0505(8) Uani 1 1 d . . . . .
H9 H 1.3332 0.9082 0.0641 0.061 Uiso 1 1 calc R U . . .
C3 C 1.1872(3) 1.0692(4) 0.3421(3) 0.0448(6) Uani 1 1 d . . . . .
H12 H 1.1505 1.1101 0.4118 0.054 Uiso 1 1 calc R U . . .
C4 C 1.3209(4) 1.0798(5) 0.2703(3) 0.0666(11) Uani 1 1 d . . . . .
H10 H 1.3739 1.1282 0.2909 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C102 C104 0.675(8) . ?
C102 C106 0.745(7) . ?
C102 O107 1.354(10) . ?
C102 C103 1.408(10) . ?
C102 O107 1.800(12) 2_665 ?
C102 C101 1.814(10) . ?
C103 C106 0.689(7) . ?
C103 O107 1.172(10) 2_665 ?
C103 C101 1.361(9) 2_665 ?
C106 O107 1.365(10) 2_665 ?
C106 C104 1.395(9) . ?
C106 O107 1.842(11) . ?
C106 C101 1.844(10) 2_665 ?
O107 C101 0.770(9) . ?
O107 C103 1.172(10) 2_665 ?
O107 C104 1.221(10) . ?
O107 C106 1.365(10) 2_665 ?
O107 C102 1.800(12) 2_665 ?
C104 C101 1.382(9) . ?
C101 C103 1.361(9) 2_665 ?
C101 C105 1.544(10) . ?
C101 C106 1.844(10) 2_665 ?
O6 C7 1.269(3) . ?
O2 C14 1.312(3) . ?
O7 C6 1.241(3) . ?
O3 N1 1.215(3) . ?
O1 C14 1.217(3) . ?
O5 C7 1.258(3) . ?
N1 O4 1.230(3) . ?
N1 C8 1.472(3) . ?
N2 C6 1.361(3) . ?
N2 C1 1.413(3) . ?
C10 C11 1.385(3) . ?
C10 C9 1.393(3) . ?
C10 C7 1.492(3) . ?
C1 C20 1.392(3) . ?
C1 C2 1.393(3) . ?
C8 C13 1.375(3) . ?
C8 C9 1.382(3) . ?
N3 C6 1.341(3) . ?
C2 C3 1.387(3) . ?
C13 C12 1.394(3) . ?
C11 C12 1.396(3) . ?
C14 C12 1.498(3) . ?
C5 C20 1.382(4) . ?
C5 C4 1.390(5) . ?
C3 C4 1.375(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
C104 C102 C106 158.1(13) . . ?
C104 C102 O107 64.1(9) . . ?
C106 C102 O107 119.8(10) . . ?
C104 C102 C103 168.1(11) . . ?
C106 C102 C103 10.5(6) . . ?
O107 C102 C103 116.0(7) . . ?
C104 C102 O107 135.5(10) . 2_665 ?
C106 C102 O107 43.9(7) . 2_665 ?
O107 C102 O107 76.1(6) . 2_665 ?
C103 C102 O107 40.6(4) . 2_665 ?
C104 C102 C101 41.4(8) . . ?
C106 C102 C101 139.6(9) . . ?
O107 C102 C101 22.7(4) . . ?
C103 C102 C101 137.8(6) . . ?
O107 C102 C101 97.3(5) 2_665 . ?
C106 C103 O107 90.6(10) . 2_665 ?
C106 C103 C101 124.9(10) . 2_665 ?
O107 C103 C101 34.4(5) 2_665 2_665 ?
C106 C103 C102 11.4(6) . . ?
O107 C103 C102 88.0(7) 2_665 . ?
C101 C103 C102 121.4(6) 2_665 . ?
C103 C106 C102 158.1(12) . . ?
C103 C106 O107 59.1(8) . 2_665 ?
C102 C106 O107 113.9(9) . 2_665 ?
C103 C106 C104 167.9(10) . . ?
C102 C106 C104 10.4(6) . . ?
O107 C106 C104 115.2(7) 2_665 . ?
C103 C106 O107 129.7(9) . . ?
C102 C106 O107 39.6(7) . . ?
O107 C106 O107 74.4(6) 2_665 . ?
C104 C106 O107 41.5(4) . . ?
C103 C106 C101 37.2(7) . 2_665 ?
C102 C106 C101 133.1(8) . 2_665 ?
O107 C106 C101 21.9(4) 2_665 2_665 ?
C104 C106 C101 136.3(5) . 2_665 ?
O107 C106 C101 94.8(5) . 2_665 ?
C101 O107 C103 86.4(11) . 2_665 ?
C101 O107 C104 84.7(10) . . ?
C103 O107 C104 161.9(9) 2_665 . ?
C101 O107 C102 114.6(12) . . ?
C103 O107 C102 153.8(9) 2_665 . ?
C104 O107 C102 29.8(4) . . ?
C101 O107 C106 116.7(11) . 2_665 ?
C103 O107 C106 30.3(4) 2_665 2_665 ?
C104 O107 C106 153.2(9) . 2_665 ?
C102 O107 C106 126.1(8) . 2_665 ?
C101 O107 C102 136.1(11) . 2_665 ?
C103 O107 C102 51.4(5) 2_665 2_665 ?
C104 O107 C102 131.4(7) . 2_665 ?
C102 O107 C102 103.9(6) . 2_665 ?
C106 O107 C102 22.2(4) 2_665 2_665 ?
C101 O107 C106 132.6(11) . . ?
C103 O107 C106 133.6(8) 2_665 . ?
C104 O107 C106 49.2(5) . . ?
C102 O107 C106 20.5(4) . . ?
C106 O107 C106 105.6(6) 2_665 . ?
C102 O107 C106 83.4(5) 2_665 . ?
C102 C104 O107 86.0(10) . . ?
C102 C104 C101 119.7(10) . . ?
O107 C104 C101 33.7(4) . . ?
C102 C104 C106 11.5(7) . . ?
O107 C104 C106 89.3(7) . . ?
C101 C104 C106 122.1(6) . . ?
O107 C101 C103 59.2(9) . 2_665 ?
O107 C101 C104 61.6(9) . . ?
C103 C101 C104 118.9(6) 2_665 . ?
O107 C101 C105 168.8(11) . . ?
C103 C101 C105 120.0(6) 2_665 . ?
C104 C101 C105 121.0(6) . . ?
O107 C101 C102 42.7(8) . . ?
C103 C101 C102 100.6(5) 2_665 . ?
C104 C101 C102 18.9(3) . . ?
C105 C101 C102 139.4(6) . . ?
O107 C101 C106 41.4(8) . 2_665 ?
C103 C101 C106 17.8(3) 2_665 2_665 ?
C104 C101 C106 101.5(5) . 2_665 ?
C105 C101 C106 137.4(6) . 2_665 ?
C102 C101 C106 83.0(4) . 2_665 ?
O3 N1 O4 123.3(2) . . ?
O3 N1 C8 118.81(19) . . ?
O4 N1 C8 117.93(19) . . ?
C6 N2 C1 127.80(19) . . ?
C11 C10 C9 120.6(2) . . ?
C11 C10 C7 121.34(19) . . ?
C9 C10 C7 118.04(19) . . ?
C20 C1 C2 119.6(2) . . ?
C20 C1 N2 115.9(2) . . ?
C2 C1 N2 124.4(2) . . ?
C13 C8 C9 123.3(2) . . ?
C13 C8 N1 117.8(2) . . ?
C9 C8 N1 118.9(2) . . ?
O5 C7 O6 124.7(2) . . ?
O5 C7 C10 117.80(19) . . ?
O6 C7 C10 117.47(19) . . ?
C3 C2 C1 119.6(2) . . ?
C8 C13 C12 118.4(2) . . ?
O7 C6 N3 121.9(2) . . ?
O7 C6 N2 121.9(2) . . ?
N3 C6 N2 116.25(19) . . ?
C10 C11 C12 120.2(2) . . ?
C8 C9 C10 117.7(2) . . ?
O1 C14 O2 124.8(2) . . ?
O1 C14 C12 122.85(19) . . ?
O2 C14 C12 112.34(18) . . ?
C20 C5 C4 120.1(3) . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 C14 119.5(2) . . ?
C11 C12 C14 120.8(2) . . ?
C5 C20 C1 120.1(3) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 119.8(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
N3 H6 O4 0.83(3) 2.25(3) 3.045(3) 159(3) 2_765
N3 H7 O1 0.85(3) 2.17(3) 3.007(3) 167(3) 2_666
N2 H8 O4 0.96(4) 2.23(4) 3.143(2) 158(3) 2_765
O2 H5 O7 0.94(5) 1.60(5) 2.534(2) 169(4) 2_666
O6 H1 O5 0.96(6) 1.70(7) 2.623(2) 160(6) 2_766
C2 H13 O7 0.93 2.26 2.846(3) 120.5 .
C20 H9 O3 0.93 2.61 3.461(3) 152.8 2_765

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'1:1 mixture of methanol and THF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NS1
_database_code_depnum_ccdc_archive 'CCDC 1471789'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'bis(n-phenylurea) 5-nitroisophthalic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 N1 O6, 2(C7 H8 N2 O1)'
_chemical_formula_sum            'C22 H21 N5 O8'
_chemical_formula_weight         483.44

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9131(7)
_cell_length_b                   9.7105(8)
_cell_length_c                   13.3778(11)
_cell_angle_alpha                71.440(7)
_cell_angle_beta                 78.479(7)
_cell_angle_gamma                83.019(7)
_cell_volume                     1073.43(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2410
_cell_measurement_theta_min      3.6530
_cell_measurement_theta_max      26.7230
_exptl_crystal_description       'rectangular needle'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_min  0.98349
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.1468
_diffrn_reflns_number            8876
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.321
_diffrn_reflns_theta_max         29.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4920
_reflns_number_gt                3277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.0588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4920
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
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_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
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_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

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NS2
_database_code_depnum_ccdc_archive 'CCDC 1471790'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'bis(n-phenylurea) bis(5-nitroisophthalic acid) '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 N1 O6, C7 H8 N2 O1'
_chemical_formula_sum            'C15 H13 N3 O7'
_chemical_formula_weight         347.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1254(3)
_cell_length_b                   12.7462(2)
_cell_length_c                   16.2905(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.286(3)
_cell_angle_gamma                90
_cell_volume                     2998.81(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.00(14)
_cell_measurement_reflns_used    6157
_cell_measurement_theta_min      4.4660
_cell_measurement_theta_max      74.0570

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             1440

_exptl_absorpt_coefficient_mu    1.068

_exptl_absorpt_correction_T_min  0.87447
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 20.7239
_diffrn_reflns_number            20298
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.485
_diffrn_reflns_theta_max         74.591
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6023
_reflns_number_gt                4827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+3.1354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6023
_refine_ls_number_parameters     555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.036(2) 0.471(3) 0.4057(19) 0.034(7) Uiso 1 1 d . . . . .
H4 H 1.1952(18) 1.285(2) 0.5708(17) 0.029(7) Uiso 1 1 d . . . . .
H5 H 1.0733(19) 0.785(2) 0.4597(18) 0.029(7) Uiso 1 1 d . . . . .
H7 H 0.8804(19) 0.680(2) 0.2368(18) 0.031(7) Uiso 1 1 d . . . . .
H11 H 0.4320(18) 0.124(2) 0.0731(18) 0.028(7) Uiso 1 1 d . . . . .
H17 H 0.811(2) 0.278(3) 0.2084(19) 0.036(8) Uiso 1 1 d . . . . .
H2 H 1.2439(18) 0.967(2) 0.6231(17) 0.025(7) Uiso 1 1 d . . . . .
H13 H 0.4405(19) 0.437(2) 0.0262(17) 0.029(7) Uiso 1 1 d . . . . .
H18 H 0.7489(19) 0.374(2) 0.0878(18) 0.030(7) Uiso 1 1 d . . . . .
H10 H 0.578(2) 0.087(2) -0.0469(19) 0.037(8) Uiso 1 1 d . . . . .
H15 H 0.662(2) 0.412(3) 0.2797(19) 0.032(7) Uiso 1 1 d . . . . .
H16 H 0.545(2) 0.224(3) 0.1617(19) 0.035(8) Uiso 1 1 d . . . . .
H3 H 1.405(2) 1.183(3) 0.785(2) 0.041(8) Uiso 1 1 d . . . . .
H14 H 0.654(2) 0.293(3) 0.2728(19) 0.035(8) Uiso 1 1 d . . . . .
H1 H 1.076(2) 0.986(3) 0.441(2) 0.057(10) Uiso 1 1 d . . . . .
H8 H 0.6854(19) 0.073(2) 0.0864(18) 0.032(7) Uiso 1 1 d . . . . .
H12 H 0.247(2) 0.247(3) -0.131(2) 0.040(8) Uiso 1 1 d . . . . .
H19 H 0.316(2) 0.420(3) -0.093(2) 0.041(8) Uiso 1 1 d . . . . .
H9 H 0.550(2) 0.256(2) -0.119(2) 0.040(8) Uiso 1 1 d . . . . .
H21 H 0.921(2) 0.096(2) 0.3327(18) 0.030(7) Uiso 1 1 d . . . . .
H25 H 0.641(2) 0.403(2) -0.0459(19) 0.036(8) Uiso 1 1 d . . . . .
H24 H 0.856(3) 0.944(4) 0.229(3) 0.081(13) Uiso 1 1 d . . . . .
H26 H 0.305(2) 0.099(3) -0.049(2) 0.053(9) Uiso 1 1 d . . . . .
H23 H 1.206(3) 0.478(3) 0.587(3) 0.067(11) Uiso 1 1 d . . . . .
H22 H 0.896(2) 0.213(3) 0.333(2) 0.057(10) Uiso 1 1 d . . . . .
H100 H 1.424(2) 1.434(3) 0.783(2) 0.055(10) Uiso 1 1 d . . . . .
O8 O 0.87845(12) 0.86747(13) 0.24597(11) 0.0304(4) Uani 1 1 d . . . . .
O7 O 0.98228(11) 0.93741(13) 0.35952(11) 0.0309(4) Uani 1 1 d . . . . .
O10 O 1.12377(13) 0.99367(14) 0.49348(12) 0.0392(5) Uani 1 1 d . . . . .
N6 N 0.90169(15) 0.48155(16) 0.26262(14) 0.0310(5) Uani 1 1 d . . . . .
O12 O 1.36419(12) 0.88924(13) 0.73895(12) 0.0343(4) Uani 1 1 d . . . . .
O6 O 1.16259(13) 0.49968(14) 0.53221(12) 0.0379(4) Uani 1 1 d . . . . .
O3 O 0.84090(14) 0.50485(16) 0.19692(13) 0.0492(6) Uani 1 1 d . . . . .
O11 O 1.44703(13) 1.00321(15) 0.82656(12) 0.0421(5) Uani 1 1 d . . . . .
C23 C 1.33286(16) 1.35909(18) 0.70844(15) 0.0259(5) Uani 1 1 d . . . . .
O9 O 1.08057(13) 1.16168(15) 0.46542(12) 0.0385(4) Uani 1 1 d . . . . .
O14 O 1.28426(12) 1.43458(13) 0.67680(12) 0.0359(4) Uani 1 1 d . . . . .
O13 O 1.41255(12) 1.36681(13) 0.76661(11) 0.0317(4) Uani 1 1 d . . . . .
N5 N 1.38450(14) 0.97980(15) 0.76180(13) 0.0280(4) Uani 1 1 d . . . . .
C28 C 1.26001(15) 1.03957(18) 0.63646(15) 0.0239(5) Uani 1 1 d . . . . .
C27 C 1.23237(15) 1.22512(18) 0.61049(15) 0.0244(5) Uani 1 1 d . . . . .
O4 O 0.92260(14) 0.39105(14) 0.28513(12) 0.0395(4) Uani 1 1 d . . . . .
C29 C 1.21011(15) 1.12100(18) 0.58686(15) 0.0252(5) Uani 1 1 d . . . . .
C25 C 1.35582(16) 1.16721(18) 0.73381(15) 0.0237(5) Uani 1 1 d . . . . .
C15 C 0.95293(16) 0.56679(18) 0.31684(15) 0.0267(5) Uani 1 1 d . . . . .
C19 C 0.97422(15) 0.75040(18) 0.34375(15) 0.0253(5) Uani 1 1 d . . . . .
O5 O 1.17133(13) 0.66426(15) 0.58250(11) 0.0376(4) Uani 1 1 d . . . . .
C18 C 1.04200(16) 0.72826(19) 0.42077(15) 0.0257(5) Uani 1 1 d . . . . .
C16 C 1.02145(16) 0.54203(19) 0.39170(16) 0.0272(5) Uani 1 1 d . . . . .
C26 C 1.30523(15) 1.24817(18) 0.68316(15) 0.0237(5) Uani 1 1 d . . . . .
C21 C 0.94625(16) 0.86071(18) 0.31740(15) 0.0252(5) Uani 1 1 d . . . . .
C17 C 1.06583(16) 0.62412(19) 0.44428(15) 0.0260(5) Uani 1 1 d . . . . .
C30 C 1.13124(16) 1.09647(19) 0.50841(15) 0.0281(5) Uani 1 1 d . . . . .
C22 C 1.13911(17) 0.6001(2) 0.52699(16) 0.0297(5) Uani 1 1 d . . . . .
C24 C 1.33138(15) 1.06518(18) 0.70896(14) 0.0240(5) Uani 1 1 d . . . . .
C20 C 0.92933(16) 0.66890(19) 0.29091(15) 0.0265(5) Uani 1 1 d . . . . .
O2 O 0.53260(13) 0.46236(13) 0.16384(12) 0.0361(4) Uani 1 1 d . . . . .
N1 N 0.52365(14) 0.28629(15) 0.14018(13) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.63721(15) 0.35542(18) 0.25354(14) 0.0337(5) Uani 1 1 d . . . . .
C10 C 0.41318(18) 0.36805(19) 0.01292(16) 0.0308(5) Uani 1 1 d . . . . .
C11 C 0.33802(19) 0.3555(2) -0.06014(17) 0.0363(6) Uani 1 1 d . . . . .
C13 C 0.33403(19) 0.1714(2) -0.03314(18) 0.0373(6) Uani 1 1 d . . . . .
C9 C 0.44851(16) 0.28158(18) 0.06420(15) 0.0260(5) Uani 1 1 d . . . . .
C8 C 0.56353(16) 0.37229(18) 0.18526(16) 0.0266(5) Uani 1 1 d . . . . .
C12 C 0.29789(19) 0.2579(2) -0.08309(18) 0.0385(6) Uani 1 1 d . . . . .
C14 C 0.40885(18) 0.18267(19) 0.03983(16) 0.0304(5) Uani 1 1 d . . . . .
O1 O 0.81550(12) 0.04373(13) 0.19673(11) 0.0329(4) Uani 1 1 d . . . . .
N3 N 0.79118(14) 0.21969(16) 0.18380(13) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.83100(16) 0.13337(18) 0.22844(16) 0.0272(5) Uani 1 1 d . . . . .
C5 C 0.61213(19) 0.1520(2) -0.02137(18) 0.0366(6) Uani 1 1 d . . . . .
C3 C 0.72714(16) 0.22426(18) 0.10017(15) 0.0257(5) Uani 1 1 d . . . . .
C4 C 0.67588(18) 0.1387(2) 0.05914(17) 0.0313(5) Uani 1 1 d . . . . .
C6 C 0.59830(18) 0.2487(2) -0.06132(17) 0.0349(6) Uani 1 1 d . . . . .
N4 N 0.88722(16) 0.15017(18) 0.30785(15) 0.0356(5) Uani 1 1 d . . . . .
C7 C 0.64913(19) 0.3337(2) -0.01995(17) 0.0347(6) Uani 1 1 d . . . . .
C2 C 0.71395(18) 0.3215(2) 0.06003(17) 0.0311(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O8 C21 1.305(3) . ?
O7 C21 1.225(3) . ?
O10 C30 1.331(3) . ?
N6 O3 1.222(3) . ?
N6 O4 1.223(3) . ?
N6 C15 1.468(3) . ?
O12 N5 1.224(3) . ?
O6 C22 1.324(3) . ?
O11 N5 1.226(3) . ?
C23 O14 1.227(3) . ?
C23 O13 1.297(3) . ?
C23 C26 1.497(3) . ?
O9 C30 1.204(3) . ?
N5 C24 1.470(3) . ?
C28 C24 1.382(3) . ?
C28 C29 1.392(3) . ?
C27 C26 1.388(3) . ?
C27 C29 1.395(3) . ?
C29 C30 1.499(3) . ?
C25 C24 1.379(3) . ?
C25 C26 1.399(3) . ?
C15 C16 1.382(3) . ?
C15 C20 1.382(3) . ?
C19 C20 1.391(3) . ?
C19 C18 1.393(3) . ?
C19 C21 1.494(3) . ?
O5 C22 1.209(3) . ?
C18 C17 1.399(3) . ?
C16 C17 1.392(3) . ?
C17 C22 1.500(3) . ?
O2 C8 1.250(3) . ?
N1 C8 1.357(3) . ?
N1 C9 1.411(3) . ?
N2 C8 1.337(3) . ?
C10 C11 1.389(4) . ?
C10 C9 1.390(3) . ?
C11 C12 1.386(4) . ?
C13 C12 1.382(4) . ?
C13 C14 1.384(4) . ?
C9 C14 1.402(3) . ?
O1 C1 1.247(3) . ?
N3 C1 1.357(3) . ?
N3 C3 1.419(3) . ?
C1 N4 1.337(3) . ?
C5 C6 1.380(4) . ?
C5 C4 1.388(4) . ?
C3 C2 1.388(3) . ?
C3 C4 1.389(3) . ?
C6 C7 1.383(4) . ?
C7 C2 1.387(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
O3 N6 O4 123.5(2) . . ?
O3 N6 C15 118.2(2) . . ?
O4 N6 C15 118.3(2) . . ?
O14 C23 O13 123.9(2) . . ?
O14 C23 C26 122.8(2) . . ?
O13 C23 C26 113.31(19) . . ?
O12 N5 O11 123.4(2) . . ?
O12 N5 C24 118.43(19) . . ?
O11 N5 C24 118.13(19) . . ?
C24 C28 C29 118.1(2) . . ?
C26 C27 C29 120.1(2) . . ?
C28 C29 C27 120.3(2) . . ?
C28 C29 C30 119.7(2) . . ?
C27 C29 C30 120.0(2) . . ?
C24 C25 C26 118.1(2) . . ?
C16 C15 C20 122.9(2) . . ?
C16 C15 N6 119.0(2) . . ?
C20 C15 N6 118.1(2) . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 C21 118.7(2) . . ?
C18 C19 C21 121.3(2) . . ?
C19 C18 C17 120.0(2) . . ?
C15 C16 C17 118.0(2) . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 C23 121.4(2) . . ?
C25 C26 C23 118.4(2) . . ?
O7 C21 O8 123.2(2) . . ?
O7 C21 C19 123.3(2) . . ?
O8 C21 C19 113.49(19) . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 C22 119.5(2) . . ?
C18 C17 C22 120.1(2) . . ?
O9 C30 O10 124.6(2) . . ?
O9 C30 C29 124.0(2) . . ?
O10 C30 C29 111.3(2) . . ?
O5 C22 O6 124.4(2) . . ?
O5 C22 C17 124.0(2) . . ?
O6 C22 C17 111.6(2) . . ?
C25 C24 C28 123.1(2) . . ?
C25 C24 N5 118.3(2) . . ?
C28 C24 N5 118.6(2) . . ?
C15 C20 C19 118.7(2) . . ?
C8 N1 C9 128.4(2) . . ?
C11 C10 C9 119.6(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C13 C14 120.2(2) . . ?
C10 C9 C14 119.1(2) . . ?
C10 C9 N1 124.0(2) . . ?
C14 C9 N1 116.9(2) . . ?
O2 C8 N2 122.0(2) . . ?
O2 C8 N1 121.4(2) . . ?
N2 C8 N1 116.5(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C14 C9 120.5(2) . . ?
C1 N3 C3 128.0(2) . . ?
O1 C1 N4 122.3(2) . . ?
O1 C1 N3 121.5(2) . . ?
N4 C1 N3 116.2(2) . . ?
C6 C5 C4 121.3(2) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 N3 116.8(2) . . ?
C4 C3 N3 123.7(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C6 C7 119.0(2) . . ?
C6 C7 C2 120.4(2) . . ?
C7 C2 C3 120.3(2) . . ?

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
C14 H11 O11 0.93(3) 2.62(3) 3.505(3) 159(2) 3_766
N3 H17 O4 0.86(3) 2.28(3) 3.082(3) 155(3) .
C10 H13 O2 0.97(3) 2.28(3) 2.848(3) 116(2) .
C2 H18 O3 0.89(3) 2.53(3) 3.402(3) 167(2) .
N2 H15 O14 0.87(3) 2.15(3) 3.010(3) 170(3) 3_776
N1 H16 O12 0.89(3) 2.30(3) 3.127(3) 155(3) 3_766
N2 H14 O12 0.87(3) 2.34(3) 3.121(3) 150(3) 3_766
O10 H1 O7 0.95(4) 1.74(4) 2.661(2) 163(3) .
C4 H8 O1 0.94(3) 2.27(3) 2.852(3) 120(2) .
N4 H21 O7 0.88(3) 2.22(3) 3.068(3) 163(3) 1_545
O8 H24 O1 1.04(5) 1.44(5) 2.479(2) 173(4) 1_565
O6 H23 O14 0.98(4) 1.68(4) 2.655(2) 175(4) 1_545
N4 H22 O4 0.89(4) 2.47(4) 3.157(3) 134(3) .
N4 H22 O5 0.89(4) 2.50(4) 3.242(3) 142(3) 3_766
O13 H100 O2 0.90(4) 1.61(4) 2.481(2) 163(3) 3_776

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

