# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smc11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-(4-nitrophenylbenzamido)urea
;
_chemical_formula_moiety         'C8 H8 N4 O4'
_chemical_formula_sum            'C8 H8 N4 O4'
_chemical_formula_weight         224.18

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   4.524(3)
_cell_length_b                   23.583(7)
_cell_length_c                   9.537(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.39(2)
_cell_angle_gamma                90.00
_cell_volume                     965.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      21.70

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9511
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2000)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            10086
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2181
_reflns_number_gt                1452
_reflns_threshold_expression     I>2sigma(I)


_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'




_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2181
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1047
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0463(4) 0.07279(8) 0.7591(2) 0.0502(5) Uani 1 1 d . . .
C2 C 0.9854(5) 0.07937(9) 0.8902(2) 0.0591(6) Uani 1 1 d . . .
H2 H 1.0508 0.0524 0.9647 0.071 Uiso 1 1 calc R . .
C3 C 0.8254(5) 0.12682(9) 0.9088(2) 0.0534(5) Uani 1 1 d . . .
H3 H 0.7826 0.1320 0.9971 0.064 Uiso 1 1 calc R . .
C4 C 0.7268(4) 0.16704(7) 0.79743(19) 0.0401(4) Uani 1 1 d . . .
C5 C 0.7939(5) 0.15897(8) 0.6669(2) 0.0494(5) Uani 1 1 d . . .
H5 H 0.7293 0.1857 0.5917 0.059 Uiso 1 1 calc R . .
C6 C 0.9556(5) 0.11162(9) 0.6474(2) 0.0531(5) Uani 1 1 d . . .
H6 H 1.0019 0.1062 0.5600 0.064 Uiso 1 1 calc R . .
C7 C 0.5601(4) 0.21780(8) 0.8288(2) 0.0436(4) Uani 1 1 d . . .
C8 C 0.4719(4) 0.34873(8) 0.7752(2) 0.0406(4) Uani 1 1 d . . .
N1 N 1.2164(4) 0.02208(8) 0.7384(3) 0.0689(6) Uani 1 1 d . . .
N2 N 0.4214(4) 0.25166(6) 0.71492(18) 0.0444(4) Uani 1 1 d . . .
H2N H 0.453(5) 0.2490(9) 0.629(2) 0.053 Uiso 1 1 d . . .
N3 N 0.2903(4) 0.30230(7) 0.7384(2) 0.0491(4) Uani 1 1 d . . .
H3N H 0.101(5) 0.3023(9) 0.741(2) 0.059 Uiso 1 1 d . . .
N4 N 0.3278(4) 0.39518(8) 0.8002(2) 0.0547(5) Uani 1 1 d . . .
H4A H 0.124(6) 0.3944(10) 0.793(2) 0.066 Uiso 1 1 d . . .
H4B H 0.432(6) 0.4266(10) 0.816(2) 0.066 Uiso 1 1 d . . .
O1 O 0.5472(4) 0.22660(7) 0.95232(16) 0.0732(5) Uani 1 1 d . . .
O2 O 0.7485(3) 0.34748(6) 0.78405(17) 0.0582(4) Uani 1 1 d . . .
O3 O 1.2650(6) -0.01507(8) 0.8313(3) 0.1137(8) Uani 1 1 d . . .
O4 O 1.3046(5) 0.01948(8) 0.6307(2) 0.0957(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0441(11) 0.0351(10) 0.0674(14) -0.0048(9) 0.0119(9) -0.0006(8)
C2 0.0690(14) 0.0447(12) 0.0594(13) 0.0110(10) 0.0143(11) 0.0027(10)
C3 0.0678(13) 0.0486(12) 0.0439(11) 0.0036(9) 0.0176(10) -0.0021(10)
C4 0.0419(10) 0.0375(10) 0.0399(10) -0.0027(7) 0.0117(8) -0.0047(8)
C5 0.0612(12) 0.0457(11) 0.0433(11) 0.0037(8) 0.0193(9) 0.0074(9)
C6 0.0590(12) 0.0511(12) 0.0526(12) -0.0070(9) 0.0224(10) 0.0038(10)
C7 0.0507(11) 0.0410(10) 0.0435(11) -0.0053(8) 0.0212(8) -0.0076(8)
C8 0.0339(9) 0.0433(10) 0.0489(10) 0.0010(8) 0.0191(8) 0.0008(8)
N1 0.0582(12) 0.0478(11) 0.0980(16) -0.0068(11) 0.0208(11) 0.0061(9)
N2 0.0510(9) 0.0402(9) 0.0478(9) -0.0010(7) 0.0239(8) 0.0057(7)
N3 0.0361(8) 0.0394(9) 0.0789(12) -0.0068(8) 0.0282(8) 0.0001(7)
N4 0.0381(9) 0.0411(9) 0.0899(13) -0.0065(9) 0.0272(9) -0.0021(8)
O1 0.1180(14) 0.0640(10) 0.0495(9) -0.0040(7) 0.0432(9) 0.0114(9)
O2 0.0330(7) 0.0582(9) 0.0900(11) -0.0105(8) 0.0290(7) -0.0024(6)
O3 0.142(2) 0.0570(12) 0.152(2) 0.0297(13) 0.0609(16) 0.0408(13)
O4 0.1023(15) 0.0768(13) 0.1187(16) -0.0118(11) 0.0503(13) 0.0278(11)

_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
C1 C6 1.366(3) . no
C1 C2 1.372(3) . no
C1 N1 1.469(3) . no
C2 C3 1.374(3) . no
C2 H2 0.9300 . no
C3 C4 1.388(3) . no
C3 H3 0.9300 . no
C4 C5 1.384(3) . no
C4 C7 1.495(3) . no
C5 C6 1.380(3) . no
C5 H5 0.9300 . no
C6 H6 0.9300 . no
C7 O1 1.215(2) . no
C7 N2 1.335(2) . no
C8 O2 1.228(2) . no
C8 N4 1.334(2) . no
C8 N3 1.347(2) . no
N1 O4 1.215(3) . no
N1 O3 1.216(3) . no
N2 N3 1.383(2) . no
N2 H2N 0.88(2) . no
N3 H3N 0.87(2) . no
N4 H4A 0.90(2) . no
N4 H4B 0.87(2) . no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.54(19) . . no
C6 C1 N1 118.8(2) . . no
C2 C1 N1 118.6(2) . . no
C1 C2 C3 118.38(19) . . no
C1 C2 H2 120.8 . . no
C3 C2 H2 120.8 . . no
C2 C3 C4 120.86(19) . . no
C2 C3 H3 119.6 . . no
C4 C3 H3 119.6 . . no
C5 C4 C3 119.02(18) . . no
C5 C4 C7 123.91(16) . . no
C3 C4 C7 117.04(16) . . no
C6 C5 C4 120.59(18) . . no
C6 C5 H5 119.7 . . no
C4 C5 H5 119.7 . . no
C1 C6 C5 118.61(19) . . no
C1 C6 H6 120.7 . . no
C5 C6 H6 120.7 . . no
O1 C7 N2 122.18(18) . . no
O1 C7 C4 120.82(18) . . no
N2 C7 C4 116.97(15) . . no
O2 C8 N4 123.52(18) . . no
O2 C8 N3 121.52(17) . . no
N4 C8 N3 114.96(16) . . no
O4 N1 O3 123.2(2) . . no
O4 N1 C1 118.7(2) . . no
O3 N1 C1 118.1(2) . . no
C7 N2 N3 120.05(16) . . no
C7 N2 H2N 123.0(14) . . no
N3 N2 H2N 114.7(14) . . no
C8 N3 N2 119.14(15) . . no
C8 N3 H3N 121.4(14) . . no
N2 N3 H3N 118.9(14) . . no
C8 N4 H4A 120.9(15) . . no
C8 N4 H4B 117.5(16) . . no
H4A N4 H4B 121(2) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(3) . . . . no
N1 C1 C2 C3 -179.83(19) . . . . no
C1 C2 C3 C4 0.2(3) . . . . no
C2 C3 C4 C5 -0.5(3) . . . . no
C2 C3 C4 C7 -178.82(19) . . . . no
C3 C4 C5 C6 0.1(3) . . . . no
C7 C4 C5 C6 178.40(18) . . . . no
C2 C1 C6 C5 -0.6(3) . . . . no
N1 C1 C6 C5 179.53(18) . . . . no
C4 C5 C6 C1 0.4(3) . . . . no
C5 C4 C7 O1 -169.29(19) . . . . no
C3 C4 C7 O1 9.0(3) . . . . no
C5 C4 C7 N2 12.3(3) . . . . no
C3 C4 C7 N2 -169.39(17) . . . . no
C6 C1 N1 O4 8.9(3) . . . . no
C2 C1 N1 O4 -170.9(2) . . . . no
C6 C1 N1 O3 -171.9(2) . . . . no
C2 C1 N1 O3 8.3(3) . . . . no
O1 C7 N2 N3 8.2(3) . . . . no
C4 C7 N2 N3 -173.41(16) . . . . no
O2 C8 N3 N2 2.2(3) . . . . no
N4 C8 N3 N2 -177.98(17) . . . . no
C7 N2 N3 C8 85.4(2) . . . . no

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.036











_database_code_depnum_ccdc_archive 'CCDC 978073'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smc21

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-(4-cyanobenzamide)urea
;
_chemical_formula_moiety         'C9 H8 N4 O2'
_chemical_formula_sum            'C9 H8 N4 O2'
_chemical_formula_weight         204.19

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.508(3)
_cell_length_b                   24.111(7)
_cell_length_c                   9.612(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.38(3)
_cell_angle_gamma                90.00
_cell_volume                     1007.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    80
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      14.93

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2000)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            6394
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1745
_reflns_number_gt                957
_reflns_threshold_expression     I>2sigma(I)


_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'


_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 > 2sigma(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.

 Several crystal specimens were tested for the X-ray analysis. They were 
 obtained from different solvents (ethanol/water, methanol/water, water, 
 acetonitrile, acetic acid) and through different crystallization methods 
 (slow evaporation, slow cooling). The results were never fully satisfying. 
 The quality of the crystals was always rather poor, with few reflections at 
 high theta values. In many cases the crystals were apparently single, but 
 actually they contained slightly misaligned components. For these reasons 
 data collection was limited to theta=25° and the final R factors are 
 relatively high.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1422P)²+0.8202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.023(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1745
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2852
_refine_ls_wR_factor_gt          0.2468
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1495(14) 0.0296(2) 0.7915(8) 0.0749(19) Uani 1 1 d . . .
C2 C 0.0267(12) 0.0776(2) 0.7715(7) 0.0576(15) Uani 1 1 d . . .
C3 C 0.0685(15) 0.0879(2) 0.6372(8) 0.0724(18) Uani 1 1 d . . .
H3 H -0.0138 0.0640 0.5609 0.087 Uiso 1 1 calc R . .
C4 C 0.2330(14) 0.1341(2) 0.6161(7) 0.0655(16) Uani 1 1 d . . .
H4 H 0.2625 0.1408 0.5254 0.079 Uiso 1 1 calc R . .
C5 C 0.3533(11) 0.16996(18) 0.7273(5) 0.0440(13) Uani 1 1 d . . .
C6 C 0.3116(14) 0.1590(2) 0.8632(6) 0.0591(15) Uani 1 1 d . . .
H6 H 0.3932 0.1827 0.9401 0.071 Uiso 1 1 calc R . .
C7 C 0.1480(14) 0.1125(2) 0.8828(7) 0.0645(16) Uani 1 1 d . . .
H7 H 0.1208 0.1050 0.9736 0.077 Uiso 1 1 calc R . .
C8 C 0.5232(12) 0.21963(19) 0.6958(6) 0.0495(14) Uani 1 1 d . . .
C9 C 0.6154(10) 0.3479(2) 0.7531(6) 0.0456(13) Uani 1 1 d . . .
N1 N 0.6583(9) 0.25260(16) 0.8058(5) 0.0468(12) Uani 1 1 d . . .
H1N H 0.642(13) 0.249(2) 0.890(6) 0.056 Uiso 1 1 d . . .
N2 N 0.7872(10) 0.30218(17) 0.7827(6) 0.0547(14) Uani 1 1 d . . .
H2N H 0.949(14) 0.302(3) 0.761(7) 0.066 Uiso 1 1 d . . .
N3 N 0.7536(11) 0.3942(2) 0.7303(6) 0.0616(16) Uani 1 1 d . . .
H3A H 0.642(14) 0.426(3) 0.712(7) 0.074 Uiso 1 1 d . . .
H3B H 0.930(17) 0.392(3) 0.730(7) 0.074 Uiso 1 1 d . . .
N4 N -0.2828(15) -0.0082(2) 0.8094(8) 0.105(2) Uani 1 1 d . . .
O1 O 0.5382(11) 0.22940(16) 0.5728(5) 0.0812(14) Uani 1 1 d . . .
O2 O 0.3370(8) 0.34649(15) 0.7459(5) 0.0643(13) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.059(4) 0.048(3) 0.108(6) 0.000(3) 0.006(4) -0.008(3)
C2 0.058(3) 0.044(3) 0.071(4) 0.000(3) 0.016(3) -0.003(3)
C3 0.080(4) 0.056(3) 0.071(5) -0.017(3) 0.000(3) -0.009(3)
C4 0.082(4) 0.058(3) 0.055(4) -0.004(3) 0.016(3) -0.004(3)
C5 0.040(3) 0.040(3) 0.051(3) 0.003(2) 0.011(2) 0.006(2)
C6 0.081(4) 0.052(3) 0.050(3) -0.003(2) 0.027(3) -0.016(3)
C7 0.074(4) 0.056(3) 0.067(4) 0.005(3) 0.026(3) -0.014(3)
C8 0.062(3) 0.047(3) 0.046(3) 0.006(2) 0.027(3) 0.008(2)
C9 0.031(3) 0.047(3) 0.065(3) 0.005(2) 0.023(2) 0.001(2)
N1 0.041(2) 0.046(2) 0.057(3) 0.006(2) 0.020(2) -0.0048(18)
N2 0.043(3) 0.043(2) 0.086(4) 0.014(2) 0.030(2) 0.002(2)
N3 0.042(3) 0.047(3) 0.104(4) 0.013(2) 0.033(3) 0.003(2)
N4 0.095(4) 0.062(3) 0.153(7) 0.000(3) 0.023(4) -0.027(3)
O1 0.125(4) 0.073(3) 0.057(3) 0.007(2) 0.046(3) -0.007(2)
O2 0.0287(19) 0.069(2) 0.103(3) 0.018(2) 0.0301(19) 0.0050(16)

_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
C1 N4 1.131(7) . no
C1 C2 1.444(8) . no
C2 C7 1.357(8) . no
C2 C3 1.375(8) . no
C3 C4 1.382(8) . no
C3 H3 0.9300 . no
C4 C5 1.370(7) . no
C4 H4 0.9300 . no
C5 C6 1.394(7) . no
C5 C8 1.495(7) . no
C6 C7 1.382(7) . no
C6 H6 0.9300 . no
C7 H7 0.9300 . no
C8 O1 1.224(6) . no
C8 N1 1.334(7) . no
C9 O2 1.239(6) . no
C9 N3 1.326(7) . no
C9 N2 1.333(6) . no
N1 N2 1.373(6) . no
N1 H1N 0.84(6) . no
N2 H2N 0.81(7) . no
N3 H3A 0.90(6) . no
N3 H3B 0.80(8) . no

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
N4 C1 C2 178.6(8) . . no
C7 C2 C3 120.0(5) . . no
C7 C2 C1 120.8(6) . . no
C3 C2 C1 119.2(6) . . no
C2 C3 C4 119.8(5) . . no
C2 C3 H3 120.1 . . no
C4 C3 H3 120.1 . . no
C5 C4 C3 120.7(6) . . no
C5 C4 H4 119.7 . . no
C3 C4 H4 119.7 . . no
C4 C5 C6 119.2(5) . . no
C4 C5 C8 117.8(5) . . no
C6 C5 C8 123.1(5) . . no
C7 C6 C5 119.5(5) . . no
C7 C6 H6 120.3 . . no
C5 C6 H6 120.3 . . no
C2 C7 C6 120.9(5) . . no
C2 C7 H7 119.6 . . no
C6 C7 H7 119.6 . . no
O1 C8 N1 121.3(5) . . no
O1 C8 C5 120.8(5) . . no
N1 C8 C5 117.9(4) . . no
O2 C9 N3 121.8(5) . . no
O2 C9 N2 120.8(4) . . no
N3 C9 N2 117.4(4) . . no
C8 N1 N2 121.0(5) . . no
C8 N1 H1N 125(4) . . no
N2 N1 H1N 113(4) . . no
C9 N2 N1 120.5(4) . . no
C9 N2 H2N 117(6) . . no
N1 N2 H2N 119(6) . . no
C9 N3 H3A 119(4) . . no
C9 N3 H3B 117(6) . . no
H3A N3 H3B 125(7) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 C2 C7 -53(33) . . . . no
N4 C1 C2 C3 127(33) . . . . no
C7 C2 C3 C4 -0.3(9) . . . . no
C1 C2 C3 C4 179.1(5) . . . . no
C2 C3 C4 C5 -0.5(9) . . . . no
C3 C4 C5 C6 0.9(8) . . . . no
C3 C4 C5 C8 -178.8(5) . . . . no
C4 C5 C6 C7 -0.5(8) . . . . no
C8 C5 C6 C7 179.2(5) . . . . no
C3 C2 C7 C6 0.7(9) . . . . no
C1 C2 C7 C6 -178.7(5) . . . . no
C5 C6 C7 C2 -0.3(9) . . . . no
C4 C5 C8 O1 4.2(7) . . . . no
C6 C5 C8 O1 -175.5(5) . . . . no
C4 C5 C8 N1 -175.5(5) . . . . no
C6 C5 C8 N1 4.8(7) . . . . no
O1 C8 N1 N2 8.0(8) . . . . no
C5 C8 N1 N2 -172.3(4) . . . . no
O2 C9 N2 N1 0.0(8) . . . . no
N3 C9 N2 N1 -179.2(5) . . . . no
C8 N1 N2 C9 85.7(6) . . . . no

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.076
















_database_code_depnum_ccdc_archive 'CCDC 978074'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smc31

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-(isonicotinoamido)urea
;
_chemical_formula_moiety         'C7 H8 N4 O2'
_chemical_formula_sum            'C7 H8 N4 O2'
_chemical_formula_weight         180.17

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.513(2)
_cell_length_b                   20.038(7)
_cell_length_c                   9.619(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.34(2)
_cell_angle_gamma                90.00
_cell_volume                     834.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      23.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9472
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2000)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            9390
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1901
_reflns_number_gt                1218
_reflns_threshold_expression     I>2sigma(I)


_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'




_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.1591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1901
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1057(5) 0.05632(10) 0.1638(2) 0.0567(6) Uani 1 1 d . . .
H1 H -0.1868 0.0271 0.0874 0.068 Uiso 1 1 calc R . .
C2 C 0.0554(5) 0.11075(9) 0.1379(2) 0.0489(5) Uani 1 1 d . . .
H2 H 0.0815 0.1178 0.0465 0.059 Uiso 1 1 calc R . .
C3 C 0.1780(4) 0.15475(8) 0.24923(18) 0.0353(4) Uani 1 1 d . . .
C4 C 0.1310(5) 0.14117(9) 0.3813(2) 0.0495(5) Uani 1 1 d . . .
H4 H 0.2086 0.1696 0.4596 0.059 Uiso 1 1 calc R . .
C5 C -0.0328(5) 0.08496(10) 0.3963(2) 0.0574(6) Uani 1 1 d . . .
H5 H -0.0601 0.0763 0.4869 0.069 Uiso 1 1 calc R . .
C6 C 0.3464(4) 0.21464(8) 0.21692(19) 0.0393(4) Uani 1 1 d . . .
C7 C 0.4306(4) 0.36894(8) 0.27197(19) 0.0351(4) Uani 1 1 d . . .
N1 N -0.1531(4) 0.04272(7) 0.2907(2) 0.0546(5) Uani 1 1 d . . .
N2 N 0.4789(3) 0.25437(7) 0.32825(17) 0.0383(4) Uani 1 1 d . . .
H2N H 0.450(4) 0.2506(9) 0.418(2) 0.046 Uiso 1 1 d . . .
N3 N 0.6103(3) 0.31406(7) 0.30442(17) 0.0432(4) Uani 1 1 d . . .
H3N H 0.794(5) 0.3149(10) 0.300(2) 0.052 Uiso 1 1 d . . .
N4 N 0.5726(4) 0.42391(8) 0.2479(2) 0.0476(5) Uani 1 1 d . . .
H4A H 0.463(5) 0.4586(10) 0.227(2) 0.057 Uiso 1 1 d . . .
H4B H 0.766(5) 0.4214(10) 0.250(2) 0.057 Uiso 1 1 d . . .
O1 O 0.3629(4) 0.22521(7) 0.09496(15) 0.0718(5) Uani 1 1 d . . .
O2 O 0.1562(3) 0.36734(6) 0.26810(16) 0.0564(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0632(14) 0.0428(11) 0.0573(13) -0.0151(10) 0.0057(11) -0.0089(10)
C2 0.0604(12) 0.0431(11) 0.0405(11) -0.0024(9) 0.0098(9) -0.0005(10)
C3 0.0419(10) 0.0267(8) 0.0371(10) 0.0020(7) 0.0106(8) 0.0037(7)
C4 0.0730(13) 0.0372(10) 0.0400(11) -0.0055(8) 0.0184(10) -0.0176(9)
C5 0.0802(15) 0.0428(11) 0.0527(12) 0.0015(9) 0.0246(11) -0.0175(10)
C6 0.0491(11) 0.0315(9) 0.0411(11) 0.0065(8) 0.0192(9) 0.0060(8)
C7 0.0297(10) 0.0339(9) 0.0460(10) 0.0023(8) 0.0177(8) 0.0000(8)
N1 0.0594(11) 0.0363(9) 0.0669(12) -0.0034(8) 0.0159(9) -0.0111(8)
N2 0.0447(9) 0.0304(7) 0.0437(9) 0.0025(7) 0.0188(7) -0.0060(7)
N3 0.0316(8) 0.0273(8) 0.0769(12) 0.0089(7) 0.0257(8) 0.0007(7)
N4 0.0338(9) 0.0302(8) 0.0842(13) 0.0109(8) 0.0255(9) 0.0039(7)
O1 0.1263(14) 0.0555(9) 0.0446(8) 0.0055(7) 0.0423(9) -0.0130(9)
O2 0.0293(7) 0.0500(8) 0.0966(12) 0.0204(7) 0.0287(7) 0.0057(6)

_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
C1 N1 1.326(3) . no
C1 C2 1.372(3) . no
C1 H1 0.9300 . no
C2 C3 1.377(2) . no
C2 H2 0.9300 . no
C3 C4 1.373(3) . no
C3 C6 1.499(2) . no
C4 C5 1.377(3) . no
C4 H4 0.9300 . no
C5 N1 1.317(2) . no
C5 H5 0.9300 . no
C6 O1 1.215(2) . no
C6 N2 1.333(2) . no
C7 O2 1.229(2) . no
C7 N4 1.327(2) . no
C7 N3 1.350(2) . no
N2 N3 1.383(2) . no
N2 H2N 0.915(19) . no
N3 H3N 0.84(2) . no
N4 H4A 0.84(2) . no
N4 H4B 0.87(2) . no

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
N1 C1 C2 124.18(18) . . no
N1 C1 H1 117.9 . . no
C2 C1 H1 117.9 . . no
C1 C2 C3 119.03(19) . . no
C1 C2 H2 120.5 . . no
C3 C2 H2 120.5 . . no
C4 C3 C2 117.37(17) . . no
C4 C3 C6 124.74(16) . . no
C2 C3 C6 117.87(16) . . no
C3 C4 C5 119.10(17) . . no
C3 C4 H4 120.4 . . no
C5 C4 H4 120.4 . . no
N1 C5 C4 124.20(19) . . no
N1 C5 H5 117.9 . . no
C4 C5 H5 117.9 . . no
O1 C6 N2 122.43(17) . . no
O1 C6 C3 120.80(17) . . no
N2 C6 C3 116.77(15) . . no
O2 C7 N4 123.26(16) . . no
O2 C7 N3 121.38(15) . . no
N4 C7 N3 115.35(15) . . no
C5 N1 C1 116.11(17) . . no
C6 N2 N3 119.98(15) . . no
C6 N2 H2N 124.1(11) . . no
N3 N2 H2N 114.2(11) . . no
C7 N3 N2 119.01(14) . . no
C7 N3 H3N 120.4(13) . . no
N2 N3 H3N 120.1(13) . . no
C7 N4 H4A 116.5(14) . . no
C7 N4 H4B 118.6(14) . . no
H4A N4 H4B 125(2) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.0(3) . . . . no
C1 C2 C3 C4 0.1(3) . . . . no
C1 C2 C3 C6 -178.57(17) . . . . no
C2 C3 C4 C5 0.3(3) . . . . no
C6 C3 C4 C5 178.81(18) . . . . no
C3 C4 C5 N1 -0.8(3) . . . . no
C4 C3 C6 O1 -175.63(18) . . . . no
C2 C3 C6 O1 2.9(3) . . . . no
C4 C3 C6 N2 5.4(3) . . . . no
C2 C3 C6 N2 -176.11(16) . . . . no
C4 C5 N1 C1 0.9(3) . . . . no
C2 C1 N1 C5 -0.5(3) . . . . no
O1 C6 N2 N3 7.7(3) . . . . no
C3 C6 N2 N3 -173.28(14) . . . . no
O2 C7 N3 N2 2.5(3) . . . . no
N4 C7 N3 N2 -178.73(16) . . . . no
C6 N2 N3 C7 86.5(2) . . . . no

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040

_database_code_depnum_ccdc_archive 'CCDC 978075'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smc42

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-(4-fluorobenzamide)urea
;
_chemical_formula_moiety         'C8 H8 F N3 O2'
_chemical_formula_sum            'C8 H8 F N3 O2'
_chemical_formula_weight         197.17

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.785(4)
_cell_length_b                   13.578(6)
_cell_length_c                   8.459(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.74(2)
_cell_angle_gamma                90.00
_cell_volume                     881.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    150
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      22.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9408
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2000)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            6324
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1995
_reflns_number_gt                1525
_reflns_threshold_expression     I>2sigma(I)


_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'


_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0785P)²+1.3229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1995
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2158
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3462(5) 0.1182(3) -0.0025(5) 0.0516(10) Uani 1 1 d . . .
C2 C 0.1748(6) 0.1113(3) -0.0718(5) 0.0547(10) Uani 1 1 d . . .
H2 H 0.1430 0.0989 -0.1810 0.066 Uiso 1 1 calc R . .
C3 C 0.0498(5) 0.1232(3) 0.0254(4) 0.0436(9) Uani 1 1 d . . .
H3 H -0.0679 0.1191 -0.0187 0.052 Uiso 1 1 calc R . .
C4 C 0.0992(4) 0.1412(2) 0.1876(4) 0.0323(7) Uani 1 1 d . . .
C5 C 0.2747(4) 0.1481(3) 0.2530(4) 0.0398(8) Uani 1 1 d . . .
H5 H 0.3077 0.1605 0.3620 0.048 Uiso 1 1 calc R . .
C6 C 0.4005(5) 0.1369(3) 0.1575(5) 0.0482(9) Uani 1 1 d . . .
H6 H 0.5183 0.1419 0.2002 0.058 Uiso 1 1 calc R . .
C7 C -0.0396(4) 0.1562(2) 0.2876(4) 0.0337(7) Uani 1 1 d . . .
C8 C -0.2685(4) 0.0797(2) 0.5224(4) 0.0299(7) Uani 1 1 d . . .
N1 N -0.0033(3) 0.1224(2) 0.4381(3) 0.0337(6) Uani 1 1 d . . .
H1N H 0.095(5) 0.096(3) 0.472(5) 0.040 Uiso 1 1 d . . .
N2 N -0.1199(4) 0.1355(2) 0.5427(3) 0.0352(6) Uani 1 1 d . . .
H2N H -0.138(5) 0.198(3) 0.594(5) 0.042 Uiso 1 1 d . . .
N3 N -0.3906(4) 0.1125(3) 0.6021(4) 0.0455(8) Uani 1 1 d . . .
H3A H -0.479(6) 0.077(3) 0.611(5) 0.055 Uiso 1 1 d . . .
H3B H -0.364(6) 0.157(3) 0.661(6) 0.055 Uiso 1 1 d . . .
O1 O -0.1770(3) 0.1982(2) 0.2355(3) 0.0457(7) Uani 1 1 d . . .
O2 O -0.2831(3) 0.00401(17) 0.4409(3) 0.0355(6) Uani 1 1 d . . .
F1 F 0.4693(4) 0.1080(3) -0.0965(4) 0.0878(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.055(2) 0.059(2) 0.048(2) 0.0054(18) 0.0287(18) 0.0073(19)
C2 0.067(3) 0.063(3) 0.0369(19) -0.0004(18) 0.0150(18) 0.002(2)
C3 0.0413(18) 0.048(2) 0.0396(19) 0.0026(15) 0.0010(15) 0.0004(16)
C4 0.0327(16) 0.0303(15) 0.0353(16) 0.0061(13) 0.0095(13) 0.0007(12)
C5 0.0332(16) 0.050(2) 0.0370(17) 0.0046(15) 0.0086(13) -0.0029(15)
C6 0.0347(17) 0.062(2) 0.050(2) 0.0093(18) 0.0146(16) 0.0030(17)
C7 0.0278(15) 0.0295(16) 0.0448(18) 0.0058(13) 0.0086(13) -0.0020(12)
C8 0.0283(15) 0.0328(16) 0.0288(14) 0.0039(12) 0.0053(11) 0.0009(12)
N1 0.0270(13) 0.0378(15) 0.0383(15) 0.0043(12) 0.0115(11) 0.0027(11)
N2 0.0325(14) 0.0361(15) 0.0397(15) -0.0062(12) 0.0138(11) -0.0042(11)
N3 0.0384(16) 0.0496(19) 0.0535(19) -0.0174(15) 0.0218(14) -0.0091(14)
O1 0.0300(12) 0.0499(15) 0.0582(16) 0.0175(12) 0.0106(11) 0.0080(11)
O2 0.0334(12) 0.0330(12) 0.0406(13) -0.0044(10) 0.0078(9) -0.0012(9)
F1 0.082(2) 0.125(3) 0.0696(19) -0.0015(18) 0.0511(16) 0.0137(19)

_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
C1 F1 1.352(4) . no
C1 C2 1.367(6) . no
C1 C6 1.372(6) . no
C2 C3 1.386(5) . no
C2 H2 0.9300 . no
C3 C4 1.383(5) . no
C3 H3 0.9300 . no
C4 C5 1.388(5) . no
C4 C7 1.494(4) . no
C5 C6 1.379(5) . no
C5 H5 0.9300 . no
C6 H6 0.9300 . no
C7 O1 1.226(4) . no
C7 N1 1.338(4) . no
C8 O2 1.231(4) . no
C8 N3 1.332(4) . no
C8 N2 1.369(4) . no
N1 N2 1.382(4) . no
N1 H1N 0.85(4) . no
N2 H2N 0.98(4) . no
N3 H3A 0.86(5) . no
N3 H3B 0.79(5) . no

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
F1 C1 C2 118.6(4) . . no
F1 C1 C6 117.9(4) . . no
C2 C1 C6 123.5(4) . . no
C1 C2 C3 118.0(4) . . no
C1 C2 H2 121.0 . . no
C3 C2 H2 121.0 . . no
C4 C3 C2 120.3(3) . . no
C4 C3 H3 119.9 . . no
C2 C3 H3 119.9 . . no
C3 C4 C5 119.8(3) . . no
C3 C4 C7 118.6(3) . . no
C5 C4 C7 121.5(3) . . no
C6 C5 C4 120.5(3) . . no
C6 C5 H5 119.7 . . no
C4 C5 H5 119.7 . . no
C1 C6 C5 117.9(3) . . no
C1 C6 H6 121.1 . . no
C5 C6 H6 121.1 . . no
O1 C7 N1 122.2(3) . . no
O1 C7 C4 122.0(3) . . no
N1 C7 C4 115.8(3) . . no
O2 C8 N3 123.8(3) . . no
O2 C8 N2 121.9(3) . . no
N3 C8 N2 114.3(3) . . no
C7 N1 N2 120.6(3) . . no
C7 N1 H1N 120(3) . . no
N2 N1 H1N 119(3) . . no
C8 N2 N1 118.7(3) . . no
C8 N2 H2N 111(2) . . no
N1 N2 H2N 124(2) . . no
C8 N3 H3A 120(3) . . no
C8 N3 H3B 116(3) . . no
H3A N3 H3B 121(4) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -179.1(4) . . . . no
C6 C1 C2 C3 -0.4(7) . . . . no
C1 C2 C3 C4 -0.3(6) . . . . no
C2 C3 C4 C5 0.6(5) . . . . no
C2 C3 C4 C7 178.4(3) . . . . no
C3 C4 C5 C6 -0.2(5) . . . . no
C7 C4 C5 C6 -178.0(3) . . . . no
F1 C1 C6 C5 179.5(4) . . . . no
C2 C1 C6 C5 0.7(7) . . . . no
C4 C5 C6 C1 -0.4(6) . . . . no
C3 C4 C7 O1 -35.2(5) . . . . no
C5 C4 C7 O1 142.6(4) . . . . no
C3 C4 C7 N1 145.9(3) . . . . no
C5 C4 C7 N1 -36.3(4) . . . . no
O1 C7 N1 N2 -1.2(5) . . . . no
C4 C7 N1 N2 177.7(3) . . . . no
O2 C8 N2 N1 17.2(5) . . . . no
N3 C8 N2 N1 -164.9(3) . . . . no
C7 N1 N2 C8 73.7(4) . . . . no

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.072





_database_code_depnum_ccdc_archive 'CCDC 978076'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_smc53

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 N-(4-chlorobenzamide)urea
;

_chemical_formula_moiety         'C8 H8 Cl N3 O2'
_chemical_formula_sum            'C8 H8 Cl N3 O2'
_chemical_formula_weight         213.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.786(4)
_cell_length_b                   4.604(3)
_cell_length_c                   30.169(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.76(3)
_cell_angle_gamma                90.00
_cell_volume                     942.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    110
_cell_measurement_theta_min      5.87
_cell_measurement_theta_max      24.07


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_process_details   
;
 SADABS (Bruker, 2000)
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_method       
;
CCD rotation images, thick slices
;
_diffrn_reflns_number            6532
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2089
_reflns_number_gt                1322
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_reduction        
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and 
Mercury (Macrae et al., 2006)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'


_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.5241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2089
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2832(3) 0.3138(4) 0.51680(7) 0.0358(5) Uani 1 1 d . . .
C2 C 0.2142(3) 0.3359(5) 0.41094(7) 0.0406(5) Uani 1 1 d . . .
C3 C 0.0811(3) 0.4580(5) 0.37612(7) 0.0410(5) Uani 1 1 d . . .
C4 C 0.1556(3) 0.6578(6) 0.34663(8) 0.0525(6) Uani 1 1 d . . .
H4 H 0.2869 0.7141 0.3490 0.063 Uiso 1 1 calc R . .
C5 C 0.0367(4) 0.7746(6) 0.31372(8) 0.0632(7) Uani 1 1 d . . .
H5 H 0.0869 0.9104 0.2940 0.076 Uiso 1 1 calc R . .
C6 C -0.1561(4) 0.6882(6) 0.31039(8) 0.0565(7) Uani 1 1 d . . .
C7 C -0.2324(3) 0.4885(6) 0.33879(8) 0.0562(7) Uani 1 1 d . . .
H7 H -0.3632 0.4307 0.3359 0.067 Uiso 1 1 calc R . .
C8 C -0.1147(3) 0.3733(6) 0.37175(7) 0.0501(6) Uani 1 1 d . . .
H8 H -0.1664 0.2377 0.3913 0.060 Uiso 1 1 calc R . .
N1 N 0.3689(3) 0.1868(4) 0.55169(7) 0.0439(5) Uani 1 1 d . . .
H1A H 0.421(4) 0.299(6) 0.5705(8) 0.053 Uiso 1 1 d . . .
H1B H 0.404(3) 0.015(6) 0.5507(7) 0.053 Uiso 1 1 d . . .
N2 N 0.2322(3) 0.1373(4) 0.48293(6) 0.0459(5) Uani 1 1 d . . .
H2N H 0.236(3) -0.042(6) 0.4866(8) 0.055 Uiso 1 1 d . . .
N3 N 0.1240(3) 0.2450(4) 0.44776(6) 0.0438(5) Uani 1 1 d . . .
H3N H 0.006(4) 0.287(5) 0.4526(8) 0.053 Uiso 1 1 d . . .
O1 O 0.2476(2) 0.5784(3) 0.51585(5) 0.0444(4) Uani 1 1 d . . .
O2 O 0.3925(2) 0.3183(4) 0.40612(5) 0.0535(4) Uani 1 1 d . . .
Cl1 Cl -0.30652(13) 0.8359(2) 0.26933(3) 0.0932(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0299(10) 0.0273(12) 0.0506(12) 0.0044(10) 0.0118(8) 0.0034(9)
C2 0.0382(12) 0.0316(12) 0.0520(12) -0.0016(10) 0.0041(9) -0.0012(10)
C3 0.0402(12) 0.0386(12) 0.0444(11) -0.0022(10) 0.0063(9) 0.0033(10)
C4 0.0464(13) 0.0557(16) 0.0553(13) 0.0084(12) 0.0043(10) -0.0038(12)
C5 0.0729(18) 0.0636(18) 0.0530(14) 0.0128(13) 0.0049(12) -0.0041(14)
C6 0.0605(16) 0.0624(17) 0.0463(13) -0.0030(12) -0.0066(11) 0.0122(14)
C7 0.0444(13) 0.0677(18) 0.0565(14) -0.0047(13) -0.0013(11) 0.0010(13)
C8 0.0416(12) 0.0587(16) 0.0502(13) 0.0041(12) 0.0052(10) -0.0022(12)
N1 0.0481(11) 0.0301(11) 0.0534(11) 0.0038(9) 0.0007(8) 0.0088(9)
N2 0.0568(12) 0.0280(10) 0.0527(11) 0.0061(9) -0.0002(9) 0.0088(10)
N3 0.0372(10) 0.0444(11) 0.0499(10) 0.0078(9) 0.0045(8) 0.0065(9)
O1 0.0451(8) 0.0219(8) 0.0663(10) 0.0048(7) 0.0070(7) 0.0062(7)
O2 0.0342(9) 0.0609(11) 0.0655(10) 0.0080(9) 0.0057(7) 0.0014(8)
Cl1 0.1050(6) 0.1020(7) 0.0716(5) 0.0102(5) -0.0348(4) 0.0153(5)

_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
C1 O1 1.242(2) . no
C1 N1 1.331(3) . no
C1 N2 1.347(3) . no
C2 O2 1.223(3) . no
C2 N3 1.343(3) . no
C2 C3 1.487(3) . no
C3 C4 1.380(3) . no
C3 C8 1.389(3) . no
C4 C5 1.380(3) . no
C4 H4 0.9300 . no
C5 C6 1.370(4) . no
C5 H5 0.9300 . no
C6 C7 1.364(4) . no
C6 Cl1 1.734(2) . no
C7 C8 1.374(3) . no
C7 H7 0.9300 . no
C8 H8 0.9300 . no
N1 H1A 0.84(2) . no
N1 H1B 0.83(3) . no
N2 N3 1.375(3) . no
N2 H2N 0.84(3) . no
N3 H3N 0.84(2) . no

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
O1 C1 N1 122.1(2) . . no
O1 C1 N2 121.8(2) . . no
N1 C1 N2 116.1(2) . . no
O2 C2 N3 122.7(2) . . no
O2 C2 C3 122.3(2) . . no
N3 C2 C3 115.04(19) . . no
C4 C3 C8 118.9(2) . . no
C4 C3 C2 118.9(2) . . no
C8 C3 C2 122.2(2) . . no
C5 C4 C3 120.5(2) . . no
C5 C4 H4 119.7 . . no
C3 C4 H4 119.7 . . no
C6 C5 C4 119.2(2) . . no
C6 C5 H5 120.4 . . no
C4 C5 H5 120.4 . . no
C7 C6 C5 121.3(2) . . no
C7 C6 Cl1 119.3(2) . . no
C5 C6 Cl1 119.4(2) . . no
C6 C7 C8 119.6(2) . . no
C6 C7 H7 120.2 . . no
C8 C7 H7 120.2 . . no
C7 C8 C3 120.4(2) . . no
C7 C8 H8 119.8 . . no
C3 C8 H8 119.8 . . no
C1 N1 H1A 116.0(17) . . no
C1 N1 H1B 121.0(16) . . no
H1A N1 H1B 120(2) . . no
C1 N2 N3 119.79(19) . . no
C1 N2 H2N 119.3(17) . . no
N3 N2 H2N 118.3(17) . . no
C2 N3 N2 120.43(19) . . no
C2 N3 H3N 121.3(16) . . no
N2 N3 H3N 116.7(16) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C4 -26.7(3) . . . . no
N3 C2 C3 C4 153.8(2) . . . . no
O2 C2 C3 C8 152.0(2) . . . . no
N3 C2 C3 C8 -27.5(3) . . . . no
C8 C3 C4 C5 0.9(4) . . . . no
C2 C3 C4 C5 179.6(2) . . . . no
C3 C4 C5 C6 -0.5(4) . . . . no
C4 C5 C6 C7 -0.3(4) . . . . no
C4 C5 C6 Cl1 179.6(2) . . . . no
C5 C6 C7 C8 0.7(4) . . . . no
Cl1 C6 C7 C8 -179.20(19) . . . . no
C6 C7 C8 C3 -0.3(4) . . . . no
C4 C3 C8 C7 -0.5(3) . . . . no
C2 C3 C8 C7 -179.2(2) . . . . no
O1 C1 N2 N3 -5.4(3) . . . . no
N1 C1 N2 N3 172.94(19) . . . . no
O2 C2 N3 N2 2.8(3) . . . . no
C3 C2 N3 N2 -177.72(19) . . . . no
C1 N2 N3 C2 95.6(3) . . . . no

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 978077'
