# 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_pm184

_audit_creation_date             2013-02-28T16:33:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N6, Cl4 Hg'
_chemical_formula_sum            'C10 H10 Cl4 Hg N6'
_chemical_formula_weight         556.63
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5400(15)
_cell_length_b                   26.670(5)
_cell_length_c                   8.200(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.002(18)
_cell_angle_gamma                90
_cell_volume                     1636(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.5
_cell_measurement_theta_max      18.3
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    2.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    10.062
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.1588
_exptl_absorpt_correction_T_max  0.2211

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.062842
_diffrn_orient_matrix_ub_12      -0.011852
_diffrn_orient_matrix_ub_13      0.09353
_diffrn_orient_matrix_ub_21      0.009794
_diffrn_orient_matrix_ub_22      0.034371
_diffrn_orient_matrix_ub_23      0.048966
_diffrn_orient_matrix_ub_31      -0.117516
_diffrn_orient_matrix_ub_32      0.009172
_diffrn_orient_matrix_ub_33      -0.062972
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         2
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 4 4
0 9 3

_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_number            3565
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3565
_reflns_number_gt                2272
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0975P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.634
_refine_diff_density_min         -1.525
_refine_diff_density_rms         0.204

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_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
Hg1 Hg 0.47755(6) 0.116271(19) 0.64145(6) 0.0585(2) Uani 1 1 d . . .
Cl1 Cl 0.5748(4) 0.20319(12) 0.6846(4) 0.0644(8) Uani 1 1 d . . .
Cl2 Cl 0.6183(4) 0.07330(16) 0.4212(3) 0.0725(10) Uani 1 1 d . . .
Cl3 Cl 0.1456(4) 0.12475(12) 0.5358(4) 0.0594(8) Uani 1 1 d . . .
Cl4 Cl 0.4895(4) 0.06102(13) 0.8802(3) 0.0583(7) Uani 1 1 d . . .
N1 N 0.4309(12) 0.1969(4) 1.0829(11) 0.053(2) Uani 1 1 d . . .
C2 C 0.4436(17) 0.2451(5) 1.0502(13) 0.054(3) Uani 1 1 d . . .
H2 H 0.3487 0.2653 1.0074 0.065 Uiso 1 1 calc R . .
N3 N 0.6048(17) 0.2601(4) 1.0856(14) 0.070(3) Uani 1 1 d . . .
H3 H 0.6419 0.2902 1.0737 0.084 Uiso 1 1 calc R . .
C4 C 0.707(2) 0.2212(7) 1.1445(19) 0.088(5) Uani 1 1 d . . .
H4 H 0.8287 0.2222 1.1802 0.105 Uiso 1 1 calc R . .
C5 C 0.5963(19) 0.1788(6) 1.1424(15) 0.068(3) Uani 1 1 d . . .
H5 H 0.6279 0.1462 1.1739 0.082 Uiso 1 1 calc R . .
C6 C 0.2738(14) 0.1671(5) 1.0544(12) 0.049(3) Uani 1 1 d . . .
N7 N 0.1521(12) 0.1865(4) 0.9462(11) 0.051(2) Uani 1 1 d . . .
C8 C 0.0008(15) 0.1591(5) 0.9200(14) 0.059(3) Uani 1 1 d . . .
H8 H -0.09 0.1724 0.8456 0.071 Uiso 1 1 calc R . .
N9 N -0.0342(12) 0.1156(4) 0.9873(11) 0.050(2) Uani 1 1 d . . .
C10 C 0.0960(14) 0.0996(4) 1.0955(11) 0.042(2) Uani 1 1 d . . .
C11 C 0.2575(14) 0.1238(4) 1.1358(13) 0.042(2) Uani 1 1 d . . .
H11 H 0.3473 0.1112 1.2127 0.05 Uiso 1 1 calc R . .
N12 N 0.0570(11) 0.0523(3) 1.1682(10) 0.044(2) Uani 1 1 d . B .
C13 C -0.1077(14) 0.0299(4) 1.1467(13) 0.047(2) Uani 1 1 d . . .
H13 H -0.2098 0.0417 1.0831 0.056 Uiso 1 1 calc R A 1
N14 N -0.0930(17) -0.0111(5) 1.2332(14) 0.069(4) Uani 0.73(12) 1 d P B 1
H14 H -0.1777 -0.0321 1.2423 0.083 Uiso 1 1 calc R B 1
C14 C -0.0930(17) -0.0111(5) 1.2332(14) 0.069(4) Uani 0.27(12) 1 d P B 2
C15 C 0.0835(19) -0.0156(5) 1.3093(14) 0.063(4) Uani 0.73(12) 1 d P B 1
H15 H 0.1279 -0.0414 1.3789 0.076 Uiso 1 1 calc R B 1
N15 N 0.0835(19) -0.0156(5) 1.3093(14) 0.063(4) Uani 0.27(12) 1 d P B 2
C16 C 0.1742(16) 0.0224(5) 1.2656(14) 0.059(3) Uani 1 1 d . . .
H16 H 0.2954 0.0283 1.2948 0.071 Uiso 1 1 calc R B 1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Hg1 Cl4 2.443(5) . ?
Hg1 Cl1 2.444(3) . ?
Hg1 Cl2 2.483(4) . ?
Hg1 Cl3 2.556(3) . ?
N1 C2 1.318(15) . ?
N1 C5 1.371(17) . ?
N1 C6 1.422(13) . ?
C2 N3 1.279(16) . ?
N3 C4 1.35(2) . ?
C4 C5 1.403(19) . ?
C6 N7 1.304(14) . ?
C6 C11 1.347(15) . ?
N7 C8 1.350(15) . ?
C8 N9 1.325(15) . ?
N9 C10 1.312(14) . ?
C10 C11 1.381(15) . ?
C10 N12 1.440(14) . ?
N12 C13 1.370(13) . ?
N12 C16 1.372(14) . ?
C13 N14 1.302(16) . ?
N14 C15 1.404(17) . ?
C15 C16 1.298(18) . ?

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
Cl4 Hg1 Cl1 118.37(14) . . ?
Cl4 Hg1 Cl2 109.08(17) . . ?
Cl1 Hg1 Cl2 113.30(12) . . ?
Cl4 Hg1 Cl3 105.28(10) . . ?
Cl1 Hg1 Cl3 103.25(10) . . ?
Cl2 Hg1 Cl3 106.39(13) . . ?
C2 N1 C5 109.3(10) . . ?
C2 N1 C6 126.2(11) . . ?
C5 N1 C6 124.4(11) . . ?
N3 C2 N1 110.5(12) . . ?
C2 N3 C4 109.0(12) . . ?
N3 C4 C5 107.7(13) . . ?
N1 C5 C4 103.5(14) . . ?
N7 C6 C11 125.4(10) . . ?
N7 C6 N1 113.1(11) . . ?
C11 C6 N1 121.5(11) . . ?
C6 N7 C8 113.8(10) . . ?
N9 C8 N7 128.0(10) . . ?
C10 N9 C8 113.3(10) . . ?
N9 C10 C11 125.1(10) . . ?
N9 C10 N12 113.0(9) . . ?
C11 C10 N12 121.9(9) . . ?
C6 C11 C10 114.4(10) . . ?
C13 N12 C16 109.3(10) . . ?
C13 N12 C10 123.8(9) . . ?
C16 N12 C10 126.9(10) . . ?
N14 C13 N12 106.3(11) . . ?
C13 N14 C15 109.1(11) . . ?
C16 C15 N14 108.2(11) . . ?
C15 C16 N12 107.0(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -0.8(13) . . . . ?
C6 N1 C2 N3 -177.8(9) . . . . ?
N1 C2 N3 C4 0.0(14) . . . . ?
C2 N3 C4 C5 0.7(15) . . . . ?
C2 N1 C5 C4 1.1(13) . . . . ?
C6 N1 C5 C4 178.3(10) . . . . ?
N3 C4 C5 N1 -1.1(14) . . . . ?
C2 N1 C6 N7 20.3(14) . . . . ?
C5 N1 C6 N7 -156.3(10) . . . . ?
C2 N1 C6 C11 -158.7(10) . . . . ?
C5 N1 C6 C11 24.6(15) . . . . ?
C11 C6 N7 C8 0.2(15) . . . . ?
N1 C6 N7 C8 -178.8(9) . . . . ?
C6 N7 C8 N9 -1.6(17) . . . . ?
N7 C8 N9 C10 2.3(18) . . . . ?
C8 N9 C10 C11 -1.7(16) . . . . ?
C8 N9 C10 N12 180.0(9) . . . . ?
N7 C6 C11 C10 0.3(15) . . . . ?
N1 C6 C11 C10 179.2(9) . . . . ?
N9 C10 C11 C6 0.5(15) . . . . ?
N12 C10 C11 C6 178.7(8) . . . . ?
N9 C10 N12 C13 -9.5(13) . . . . ?
C11 C10 N12 C13 172.1(9) . . . . ?
N9 C10 N12 C16 169.5(10) . . . . ?
C11 C10 N12 C16 -8.9(15) . . . . ?
C16 N12 C13 N14 2.3(12) . . . . ?
C10 N12 C13 N14 -178.5(9) . . . . ?
N12 C13 N14 C15 -0.8(12) . . . . ?
C13 N14 C15 C16 -1.0(14) . . . . ?
N14 C15 C16 N12 2.4(13) . . . . ?
C13 N12 C16 C15 -3.0(13) . . . . ?
C10 N12 C16 C15 177.9(9) . . . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1012937'
#######################################################################
#
#                 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_pm186

_audit_creation_date             2013-03-13T19:26:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N6, 2(Cl), H2 O'
_chemical_formula_sum            'C10 H12 Cl2 N6 O'
_chemical_formula_weight         303.16
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.3030(18)
_cell_length_b                   8.599(2)
_cell_length_c                   21.577(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.32(3)
_cell_angle_gamma                90
_cell_volume                     1351.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    18
_cell_measurement_theta_min      10
_cell_measurement_theta_max      18
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale orange'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.49
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.9303

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.097711
_diffrn_orient_matrix_ub_12      0.057905
_diffrn_orient_matrix_ub_13      0.025522
_diffrn_orient_matrix_ub_21      -0.036814
_diffrn_orient_matrix_ub_22      0.098267
_diffrn_orient_matrix_ub_23      -0.022325
_diffrn_orient_matrix_ub_31      -0.089178
_diffrn_orient_matrix_ub_32      0.022671
_diffrn_orient_matrix_ub_33      0.031787
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 -9

_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_number            2445
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2381
_reflns_number_gt                1461
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0520P)²+0.3285P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.13408(13) -0.23560(12) 0.47911(4) 0.0509(3) Uani 1 1 d . . .
Cl2 Cl 0.45341(13) 0.25120(12) 0.38371(4) 0.0532(3) Uani 1 1 d . . .
N1 N 0.2733(4) 0.1590(3) 0.60409(12) 0.0338(7) Uani 1 1 d . . .
N3 N 0.3790(4) 0.2395(4) 0.51966(15) 0.0453(8) Uani 1 1 d . . .
H3 H 0.402(5) 0.247(4) 0.4770(18) 0.054 Uiso 1 1 d . . .
N7 N 0.1552(4) 0.1373(3) 0.70004(12) 0.0391(7) Uani 1 1 d . . .
N9 N 0.0179(4) -0.0964(3) 0.73362(12) 0.0383(7) Uani 1 1 d . . .
N12 N -0.0071(4) -0.3172(3) 0.67164(12) 0.0334(7) Uani 1 1 d . . .
N14 N -0.0836(4) -0.5334(4) 0.62836(14) 0.0446(8) Uani 1 1 d . . .
H14 H -0.102(5) -0.597(4) 0.5971(16) 0.054 Uiso 1 1 d . . .
C2 C 0.2998(5) 0.1222(4) 0.54468(15) 0.0389(9) Uani 1 1 d . . .
H2 H 0.2671 0.0289 0.525 0.047 Uiso 1 1 calc R . .
C4 C 0.4058(5) 0.3570(5) 0.56247(17) 0.0515(10) Uani 1 1 d . . .
H4 H 0.4595 0.4531 0.5561 0.062 Uiso 1 1 calc R . .
C5 C 0.3403(5) 0.3070(4) 0.61503(17) 0.0439(9) Uani 1 1 d . . .
H5 H 0.3399 0.362 0.6521 0.053 Uiso 1 1 calc R . .
C6 C 0.1849(4) 0.0655(4) 0.64718(14) 0.0322(8) Uani 1 1 d . . .
C8 C 0.0717(5) 0.0503(4) 0.74056(16) 0.0416(9) Uani 1 1 d . . .
H8 H 0.0484 0.0978 0.7779 0.05 Uiso 1 1 calc R . .
C10 C 0.0526(4) -0.1601(4) 0.67969(15) 0.0312(8) Uani 1 1 d . . .
C11 C 0.1370(4) -0.0849(4) 0.63348(14) 0.0347(8) Uani 1 1 d . . .
H11 H 0.1597 -0.1323 0.5961 0.042 Uiso 1 1 calc R . .
C13 C -0.0130(5) -0.3964(4) 0.61840(16) 0.0426(9) Uani 1 1 d . . .
H13 H 0.0261 -0.3608 0.5809 0.051 Uiso 1 1 calc R . .
C15 C -0.1277(5) -0.5442(4) 0.68855(18) 0.0477(10) Uani 1 1 d . . .
H15 H -0.1808 -0.6292 0.7069 0.057 Uiso 1 1 calc R . .
C16 C -0.0802(5) -0.4093(4) 0.71628(16) 0.0411(9) Uani 1 1 d . . .
H16 H -0.0937 -0.3827 0.7575 0.049 Uiso 1 1 calc R . .
O1 O 0.2968(4) -0.0909(3) 0.35564(12) 0.0625(8) Uani 1 1 d D . .
H0 H 0.245(6) -0.121(4) 0.3910(14) 0.094 Uiso 1 1 d D . .
H1 H 0.341(6) 0.005(3) 0.3644(18) 0.094 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N1 C2 1.349(4) . ?
N1 C5 1.378(4) . ?
N1 C6 1.420(4) . ?
N3 C2 1.300(4) . ?
N3 C4 1.373(5) . ?
N3 H3 0.95(4) . ?
N7 C6 1.329(4) . ?
N7 C8 1.332(4) . ?
N9 C8 1.326(4) . ?
N9 C10 1.328(4) . ?
N12 C13 1.334(4) . ?
N12 C16 1.385(4) . ?
N12 C10 1.426(4) . ?
N14 C13 1.310(4) . ?
N14 C15 1.365(4) . ?
N14 H14 0.87(4) . ?
C2 H2 0.93 . ?
C4 C5 1.335(5) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?
C6 C11 1.367(5) . ?
C8 H8 0.93 . ?
C10 C11 1.373(4) . ?
C11 H11 0.93 . ?
C13 H13 0.93 . ?
C15 C16 1.338(5) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
O1 H0 0.914(18) . ?
O1 H1 0.902(18) . ?

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
C2 N1 C5 107.8(3) . . ?
C2 N1 C6 126.5(3) . . ?
C5 N1 C6 125.7(3) . . ?
C2 N3 C4 109.7(3) . . ?
C2 N3 H3 125(2) . . ?
C4 N3 H3 125(2) . . ?
C6 N7 C8 114.5(3) . . ?
C8 N9 C10 114.7(3) . . ?
C13 N12 C16 108.5(3) . . ?
C13 N12 C10 125.3(3) . . ?
C16 N12 C10 126.0(3) . . ?
C13 N14 C15 109.9(3) . . ?
C13 N14 H14 119(2) . . ?
C15 N14 H14 131(2) . . ?
N3 C2 N1 108.2(3) . . ?
N3 C2 H2 125.9 . . ?
N1 C2 H2 125.9 . . ?
C5 C4 N3 107.0(3) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N1 107.3(3) . . ?
C4 C5 H5 126.4 . . ?
N1 C5 H5 126.4 . . ?
N7 C6 C11 124.7(3) . . ?
N7 C6 N1 114.3(3) . . ?
C11 C6 N1 121.0(3) . . ?
N9 C8 N7 127.3(3) . . ?
N9 C8 H8 116.4 . . ?
N7 C8 H8 116.4 . . ?
N9 C10 C11 124.6(3) . . ?
N9 C10 N12 114.9(3) . . ?
C11 C10 N12 120.5(3) . . ?
C6 C11 C10 114.2(3) . . ?
C6 C11 H11 122.9 . . ?
C10 C11 H11 122.9 . . ?
N14 C13 N12 107.8(3) . . ?
N14 C13 H13 126.1 . . ?
N12 C13 H13 126.1 . . ?
C16 C15 N14 107.2(3) . . ?
C16 C15 H15 126.4 . . ?
N14 C15 H15 126.4 . . ?
C15 C16 N12 106.6(3) . . ?
C15 C16 H16 126.7 . . ?
N12 C16 H16 126.7 . . ?
H0 O1 H1 105(2) . . ?

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
C4 N3 C2 N1 -0.2(4) . . . . ?
C5 N1 C2 N3 0.1(4) . . . . ?
C6 N1 C2 N3 177.5(3) . . . . ?
C2 N3 C4 C5 0.2(4) . . . . ?
N3 C4 C5 N1 -0.1(4) . . . . ?
C2 N1 C5 C4 -0.1(4) . . . . ?
C6 N1 C5 C4 -177.5(3) . . . . ?
C8 N7 C6 C11 -0.3(5) . . . . ?
C8 N7 C6 N1 179.8(3) . . . . ?
C2 N1 C6 N7 -171.5(3) . . . . ?
C5 N1 C6 N7 5.5(5) . . . . ?
C2 N1 C6 C11 8.5(5) . . . . ?
C5 N1 C6 C11 -174.5(3) . . . . ?
C10 N9 C8 N7 -0.3(5) . . . . ?
C6 N7 C8 N9 0.4(5) . . . . ?
C8 N9 C10 C11 0.0(5) . . . . ?
C8 N9 C10 N12 -179.2(3) . . . . ?
C13 N12 C10 N9 169.1(3) . . . . ?
C16 N12 C10 N9 -6.2(4) . . . . ?
C13 N12 C10 C11 -10.2(5) . . . . ?
C16 N12 C10 C11 174.5(3) . . . . ?
N7 C6 C11 C10 0.1(5) . . . . ?
N1 C6 C11 C10 -180.0(3) . . . . ?
N9 C10 C11 C6 0.0(5) . . . . ?
N12 C10 C11 C6 179.2(3) . . . . ?
C15 N14 C13 N12 1.0(4) . . . . ?
C16 N12 C13 N14 -0.9(4) . . . . ?
C10 N12 C13 N14 -176.9(3) . . . . ?
C13 N14 C15 C16 -0.7(4) . . . . ?
N14 C15 C16 N12 0.1(4) . . . . ?
C13 N12 C16 C15 0.5(4) . . . . ?
C10 N12 C16 C15 176.4(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 H3 Cl2 0.95(4) 2.07(4) 3.025(3) 177(3) .
N14 H14 Cl1 0.87(4) 2.18(4) 3.054(3) 176(3) 3_546
O1 H0 Cl1 0.914(18) 2.339(18) 3.246(3) 171(4) .
O1 H1 Cl2 0.902(18) 2.296(18) 3.198(3) 178(3) .

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1012938'
#######################################################################
#
#                 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_pm187

_audit_creation_date             2013-03-20T09:23:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N6, Cd Cl4'
_chemical_formula_sum            'C10 H10 Cd Cl4 N6'
_chemical_formula_weight         468.44
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.478(2)
_cell_length_b                   26.697(5)
_cell_length_c                   8.270(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.55(2)
_cell_angle_gamma                90
_cell_volume                     1640.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.6
_cell_measurement_theta_max      18.2
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.7568
_exptl_absorpt_correction_T_max  0.7882

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.113238
_diffrn_orient_matrix_ub_12      -0.018758
_diffrn_orient_matrix_ub_13      0.012848
_diffrn_orient_matrix_ub_21      0.07004
_diffrn_orient_matrix_ub_22      -0.031911
_diffrn_orient_matrix_ub_23      0.014025
_diffrn_orient_matrix_ub_31      0.019477
_diffrn_orient_matrix_ub_32      0.005725
_diffrn_orient_matrix_ub_33      0.120214
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -2 3

_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_number            2877
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2877
_reflns_number_gt                2016
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0485P)²+0.1258P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2877
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.12

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cd1 Cd 0.47548(6) 0.116487(18) 0.13352(6) 0.04467(17) Uani 1 1 d . . .
Cl1 Cl 0.5790(2) 0.20217(6) 0.1890(2) 0.0558(4) Uani 1 1 d . . .
Cl2 Cl 0.1491(2) 0.12562(6) 0.0370(2) 0.0545(4) Uani 1 1 d . . .
Cl3 Cl 0.4873(2) 0.06312(6) 0.37517(19) 0.0496(4) Uani 1 1 d . . .
Cl4 Cl 0.6173(2) 0.07385(7) -0.0796(2) 0.0602(5) Uani 1 1 d . . .
N1 N 1.4358(7) 0.19566(19) 0.5873(6) 0.0435(13) Uani 1 1 d . . .
N3 N 1.6139(9) 0.2579(2) 0.5940(7) 0.0665(18) Uani 1 1 d . . .
H3 H 1.6546 0.2878 0.5857 0.08 Uiso 1 1 calc R . .
N7 N 1.1521(7) 0.18643(19) 0.4475(6) 0.0482(13) Uani 1 1 d . . .
N9 N 0.9651(7) 0.1167(2) 0.4860(6) 0.0472(13) Uani 1 1 d . . .
N12 N 1.0512(6) 0.05254(17) 0.6659(5) 0.0361(11) Uani 1 1 d . . .
N14 N 0.8940(8) -0.0105(2) 0.7241(7) 0.0566(15) Uani 1 1 d . . .
H14 H 0.8055 -0.0308 0.7288 0.068 Uiso 1 1 calc R . .
C2 C 1.4454(10) 0.2447(3) 0.5529(8) 0.0526(17) Uani 1 1 d . . .
H2 H 1.3517 0.2652 0.5089 0.063 Uiso 1 1 calc R . .
C4 C 1.7145(11) 0.2184(3) 0.6509(10) 0.074(2) Uani 1 1 d . . .
H4 H 1.8374 0.2184 0.6853 0.089 Uiso 1 1 calc R . .
C5 C 1.6018(9) 0.1789(3) 0.6482(8) 0.0593(19) Uani 1 1 d . . .
H5 H 1.6318 0.1464 0.6817 0.071 Uiso 1 1 calc R . .
C6 C 1.2738(8) 0.1672(2) 0.5569(7) 0.0412(15) Uani 1 1 d . . .
C8 C 1.0025(9) 0.1595(3) 0.4181(8) 0.0576(19) Uani 1 1 d . . .
H8 H 0.9141 0.1724 0.341 0.069 Uiso 1 1 calc R . .
C10 C 1.0919(8) 0.0995(2) 0.5944(7) 0.0381(14) Uani 1 1 d . . .
C11 C 1.2556(7) 0.1226(2) 0.6383(7) 0.0368(13) Uani 1 1 d . . .
H11 H 1.3442 0.1095 0.7148 0.044 Uiso 1 1 calc R . .
C13 C 0.8880(8) 0.0312(2) 0.6423(7) 0.0413(15) Uani 1 1 d . . .
H13 H 0.7879 0.0439 0.5785 0.05 Uiso 1 1 calc R . .
C15 C 1.0678(10) -0.0169(3) 0.8031(8) 0.0539(17) Uani 1 1 d . . .
H15 H 1.1087 -0.0437 0.8691 0.065 Uiso 1 1 calc R . .
C16 C 1.1634(8) 0.0223(2) 0.7665(7) 0.0466(16) Uani 1 1 d . . .
H16 H 1.284 0.0284 0.8021 0.056 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Cd1 Cl4 2.4400(17) . ?
Cd1 Cl1 2.4418(18) . ?
Cd1 Cl3 2.4476(17) . ?
Cd1 Cl2 2.4916(18) . ?
N1 C2 1.342(8) . ?
N1 C5 1.361(8) . ?
N1 C6 1.428(7) . ?
N3 C2 1.315(9) . ?
N3 C4 1.348(10) . ?
N7 C6 1.312(7) . ?
N7 C8 1.328(8) . ?
N9 C10 1.310(7) . ?
N9 C8 1.318(8) . ?
N12 C13 1.341(7) . ?
N12 C16 1.373(7) . ?
N12 C10 1.435(7) . ?
N14 C13 1.300(8) . ?
N14 C15 1.397(8) . ?
C4 C5 1.349(9) . ?
C6 C11 1.382(8) . ?
C10 C11 1.382(8) . ?
C15 C16 1.322(9) . ?

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
Cl4 Cd1 Cl1 114.71(7) . . ?
Cl4 Cd1 Cl3 109.87(6) . . ?
Cl1 Cd1 Cl3 114.25(6) . . ?
Cl4 Cd1 Cl2 107.76(6) . . ?
Cl1 Cd1 Cl2 104.28(6) . . ?
Cl3 Cd1 Cl2 105.15(6) . . ?
C2 N1 C5 109.3(5) . . ?
C2 N1 C6 123.1(6) . . ?
C5 N1 C6 127.6(6) . . ?
C2 N3 C4 111.2(6) . . ?
C6 N7 C8 114.7(6) . . ?
C10 N9 C8 115.0(5) . . ?
C13 N12 C16 108.8(5) . . ?
C13 N12 C10 123.0(5) . . ?
C16 N12 C10 128.3(5) . . ?
C13 N14 C15 108.8(6) . . ?
N3 C2 N1 106.2(7) . . ?
N3 C4 C5 106.4(7) . . ?
C4 C5 N1 106.9(7) . . ?
N7 C6 C11 125.0(6) . . ?
N7 C6 N1 114.9(6) . . ?
C11 C6 N1 120.1(6) . . ?
N9 C8 N7 127.3(6) . . ?
N9 C10 C11 125.0(6) . . ?
N9 C10 N12 114.7(5) . . ?
C11 C10 N12 120.3(5) . . ?
C10 C11 C6 112.9(5) . . ?
N14 C13 N12 108.2(6) . . ?
C16 C15 N14 107.2(6) . . ?
C15 C16 N12 107.1(6) . . ?

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
C4 N3 C2 N1 1.3(8) . . . . ?
C5 N1 C2 N3 -0.8(7) . . . . ?
C6 N1 C2 N3 -178.9(5) . . . . ?
C2 N3 C4 C5 -1.4(9) . . . . ?
N3 C4 C5 N1 0.8(8) . . . . ?
C2 N1 C5 C4 0.0(8) . . . . ?
C6 N1 C5 C4 178.0(6) . . . . ?
C8 N7 C6 C11 0.3(9) . . . . ?
C8 N7 C6 N1 179.2(5) . . . . ?
C2 N1 C6 N7 21.4(8) . . . . ?
C5 N1 C6 N7 -156.4(6) . . . . ?
C2 N1 C6 C11 -159.6(5) . . . . ?
C5 N1 C6 C11 22.6(9) . . . . ?
C10 N9 C8 N7 0.1(11) . . . . ?
C6 N7 C8 N9 0.0(11) . . . . ?
C8 N9 C10 C11 -0.5(9) . . . . ?
C8 N9 C10 N12 -179.1(5) . . . . ?
C13 N12 C10 N9 -9.1(8) . . . . ?
C16 N12 C10 N9 171.2(6) . . . . ?
C13 N12 C10 C11 172.2(5) . . . . ?
C16 N12 C10 C11 -7.5(9) . . . . ?
N9 C10 C11 C6 0.8(8) . . . . ?
N12 C10 C11 C6 179.3(5) . . . . ?
N7 C6 C11 C10 -0.6(8) . . . . ?
N1 C6 C11 C10 -179.6(5) . . . . ?
C15 N14 C13 N12 -0.5(7) . . . . ?
C16 N12 C13 N14 0.4(7) . . . . ?
C10 N12 C13 N14 -179.4(5) . . . . ?
C13 N14 C15 C16 0.4(7) . . . . ?
N14 C15 C16 N12 -0.2(7) . . . . ?
C13 N12 C16 C15 -0.1(7) . . . . ?
C10 N12 C16 C15 179.6(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 Cl2 0.86 2.35 3.161(7) 158.3 4_766
N14 H14 Cl3 0.86 2.42 3.201(6) 151.5 3_656

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1012939'
#######################################################################
#
#                 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_pm190

_audit_creation_date             2013-08-21T18:18:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N6, 2(N O3), H N O3'
_chemical_formula_sum            'C10 H11 N9 O9'
_chemical_formula_weight         401.28
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5097(19)
_cell_length_b                   11.521(3)
_cell_length_c                   14.622(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.794(17)
_cell_angle_gamma                90
_cell_volume                     1600.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      21.4
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.4244
_exptl_absorpt_correction_T_max  0.9696

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.042593
_diffrn_orient_matrix_ub_12      0.079103
_diffrn_orient_matrix_ub_13      -0.002996
_diffrn_orient_matrix_ub_21      0.095551
_diffrn_orient_matrix_ub_22      -0.035502
_diffrn_orient_matrix_ub_23      -0.002777
_diffrn_orient_matrix_ub_31      -0.010972
_diffrn_orient_matrix_ub_32      -0.001974
_diffrn_orient_matrix_ub_33      -0.068406
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         2
_diffrn_standards_interval_count 66
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        63
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -4 0
5 -3 0

_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_number            2818
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2818
_reflns_number_gt                1759
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0733P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C2 C 0.0377(4) 0.1567(3) 0.4156(2) 0.0406(8) Uani 1 1 d . . .
C4 C -0.1831(3) 0.1101(3) 0.4367(2) 0.0420(8) Uani 1 1 d . . .
C5 C -0.1669(3) 0.1172(3) 0.3460(2) 0.0389(8) Uani 1 1 d . . .
C6 C 0.0385(3) 0.1616(2) 0.24881(18) 0.0327(7) Uani 1 1 d . . .
C8 C 0.2379(3) 0.1920(3) 0.1768(2) 0.0450(9) Uani 1 1 d . . .
C10 C 0.0419(3) 0.1637(2) 0.09059(19) 0.0322(7) Uani 1 1 d . . .
C11 C -0.0372(3) 0.1519(3) 0.1670(2) 0.0345(7) Uani 1 1 d . . .
C13 C 0.0500(4) 0.1584(3) -0.07659(19) 0.0390(8) Uani 1 1 d . . .
C15 C -0.1689(4) 0.1169(3) -0.1155(2) 0.0413(8) Uani 1 1 d . . .
C16 C -0.1588(3) 0.1232(3) -0.0244(2) 0.0373(8) Uani 1 1 d . . .
N1 N -0.0287(2) 0.1470(2) 0.33365(15) 0.0324(6) Uani 1 1 d . . .
N2 N -0.3503(3) 0.3355(2) 0.16977(17) 0.0396(7) Uani 1 1 d . . .
N3 N -0.0540(3) 0.1343(2) 0.47825(17) 0.0407(7) Uani 1 1 d . . .
N4 N -0.4237(3) -0.0351(3) 0.13265(18) 0.0484(7) Uani 1 1 d . . .
N5 N -0.5987(3) 0.0354(3) 0.3797(2) 0.0542(8) Uani 1 1 d . . .
N7 N 0.1750(2) 0.1803(2) 0.25695(16) 0.0393(7) Uani 1 1 d . . .
N9 N 0.1783(3) 0.1844(2) 0.09396(16) 0.0395(7) Uani 1 1 d . . .
N12 N -0.0205(2) 0.14937(19) 0.00098(15) 0.0307(6) Uani 1 1 d . . .
N14 N -0.0385(3) 0.1396(2) -0.14613(17) 0.0418(7) Uani 1 1 d . . .
O1 O -0.2933(2) 0.3172(2) 0.09688(14) 0.0554(7) Uani 1 1 d . . .
O2 O -0.2860(2) 0.3293(2) 0.24418(15) 0.0620(7) Uani 1 1 d . . .
O3 O -0.4810(2) 0.3637(2) 0.16711(13) 0.0472(6) Uani 1 1 d . . .
O4 O -0.3604(3) 0.0565(2) 0.14848(16) 0.0688(8) Uani 1 1 d . . .
O5 O -0.4015(3) -0.0963(2) 0.06734(18) 0.0800(9) Uani 1 1 d . . .
O6 O -0.5177(2) -0.0667(2) 0.18832(16) 0.0581(7) Uani 1 1 d . . .
O7 O -0.6779(3) -0.0436(2) 0.35877(18) 0.0796(9) Uani 1 1 d . . .
O8 O -0.5009(2) 0.0646(2) 0.32257(17) 0.0644(8) Uani 1 1 d . . .
O9 O -0.6033(3) 0.0935(2) 0.44834(18) 0.0808(9) Uani 1 1 d . . .
H2 H 0.126(3) 0.181(3) 0.428(2) 0.057(11) Uiso 1 1 d . . .
H3 H -0.033(3) 0.139(2) 0.540(2) 0.052(10) Uiso 1 1 d . . .
H4 H -0.273(4) 0.094(3) 0.468(3) 0.077(11) Uiso 1 1 d . . .
H5 H -0.240(3) 0.113(2) 0.300(2) 0.035(8) Uiso 1 1 d . . .
H8 H 0.335(3) 0.210(2) 0.1866(18) 0.040(8) Uiso 1 1 d . . .
H11 H -0.122(3) 0.146(2) 0.161(2) 0.037(9) Uiso 1 1 d . . .
H13 H 0.137(3) 0.178(2) -0.0712(19) 0.033(9) Uiso 1 1 d . . .
H14 H -0.012(4) 0.142(3) -0.207(3) 0.084(13) Uiso 1 1 d . . .
H15 H -0.248(3) 0.110(2) -0.153(2) 0.042(9) Uiso 1 1 d . . .
H16 H -0.217(3) 0.120(3) 0.015(2) 0.048(9) Uiso 1 1 d . . .
H8N H -0.510(4) 0.006(4) 0.270(3) 0.114(16) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C2 N3 1.321(4) . ?
C2 N1 1.332(4) . ?
C2 H2 0.90(3) . ?
C4 C5 1.346(4) . ?
C4 N3 1.371(4) . ?
C4 H4 1.00(3) . ?
C5 N1 1.378(4) . ?
C5 H5 0.94(3) . ?
C6 N7 1.316(3) . ?
C6 C11 1.370(4) . ?
C6 N1 1.433(3) . ?
C8 N9 1.314(4) . ?
C8 N7 1.348(4) . ?
C8 H8 0.95(3) . ?
C10 N9 1.317(3) . ?
C10 C11 1.384(4) . ?
C10 N12 1.422(4) . ?
C11 H11 0.81(3) . ?
C13 N14 1.306(4) . ?
C13 N12 1.349(3) . ?
C13 H13 0.86(3) . ?
C15 C16 1.333(4) . ?
C15 N14 1.364(4) . ?
C15 H15 0.92(3) . ?
C16 N12 1.382(4) . ?
C16 H16 0.82(3) . ?
N2 O2 1.224(3) . ?
N2 O1 1.237(3) . ?
N2 O3 1.284(3) . ?
N3 H3 0.92(3) . ?
N4 O5 1.214(3) . ?
N4 O4 1.232(3) . ?
N4 O6 1.291(3) . ?
N5 O9 1.209(3) . ?
N5 O7 1.211(4) . ?
N5 O8 1.323(3) . ?
N14 H14 0.93(4) . ?
O6 H8N 1.45(5) . ?
O8 H8N 1.03(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
N3 C2 N1 107.9(3) . . ?
N3 C2 H2 125(2) . . ?
N1 C2 H2 127(2) . . ?
C5 C4 N3 106.3(3) . . ?
C5 C4 H4 127(2) . . ?
N3 C4 H4 127(2) . . ?
C4 C5 N1 107.4(3) . . ?
C4 C5 H5 125.6(17) . . ?
N1 C5 H5 126.4(17) . . ?
N7 C6 C11 124.5(3) . . ?
N7 C6 N1 114.9(3) . . ?
C11 C6 N1 120.6(3) . . ?
N9 C8 N7 127.2(3) . . ?
N9 C8 H8 121.7(16) . . ?
N7 C8 H8 111.1(16) . . ?
N9 C10 C11 124.1(3) . . ?
N9 C10 N12 114.9(2) . . ?
C11 C10 N12 120.9(3) . . ?
C6 C11 C10 114.4(3) . . ?
C6 C11 H11 125(2) . . ?
C10 C11 H11 120(2) . . ?
N14 C13 N12 108.3(3) . . ?
N14 C13 H13 134.2(19) . . ?
N12 C13 H13 117.4(19) . . ?
C16 C15 N14 107.2(3) . . ?
C16 C15 H15 128.8(18) . . ?
N14 C15 H15 123.4(18) . . ?
C15 C16 N12 107.5(3) . . ?
C15 C16 H16 133(2) . . ?
N12 C16 H16 119(2) . . ?
C2 N1 C5 108.4(2) . . ?
C2 N1 C6 123.9(3) . . ?
C5 N1 C6 127.6(2) . . ?
O2 N2 O1 122.4(3) . . ?
O2 N2 O3 118.9(2) . . ?
O1 N2 O3 118.8(3) . . ?
C2 N3 C4 109.9(3) . . ?
C2 N3 H3 123.7(19) . . ?
C4 N3 H3 126.4(19) . . ?
O5 N4 O4 122.9(3) . . ?
O5 N4 O6 119.0(3) . . ?
O4 N4 O6 118.1(3) . . ?
O9 N5 O7 125.3(3) . . ?
O9 N5 O8 116.0(3) . . ?
O7 N5 O8 118.6(3) . . ?
C6 N7 C8 114.5(3) . . ?
C8 N9 C10 115.2(2) . . ?
C13 N12 C16 107.3(3) . . ?
C13 N12 C10 124.3(3) . . ?
C16 N12 C10 128.4(2) . . ?
C13 N14 C15 109.7(3) . . ?
C13 N14 H14 123(2) . . ?
C15 N14 H14 128(2) . . ?
N4 O6 H8N 110.0(16) . . ?
N5 O8 H8N 106(2) . . ?

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
N3 C4 C5 N1 -0.7(4) . . . . ?
N7 C6 C11 C10 -0.2(5) . . . . ?
N1 C6 C11 C10 -177.7(2) . . . . ?
N9 C10 C11 C6 -1.0(4) . . . . ?
N12 C10 C11 C6 176.5(3) . . . . ?
N14 C15 C16 N12 -0.4(4) . . . . ?
N3 C2 N1 C5 0.0(3) . . . . ?
N3 C2 N1 C6 -178.0(3) . . . . ?
C4 C5 N1 C2 0.5(4) . . . . ?
C4 C5 N1 C6 178.3(3) . . . . ?
N7 C6 N1 C2 3.2(4) . . . . ?
C11 C6 N1 C2 -179.0(3) . . . . ?
N7 C6 N1 C5 -174.3(3) . . . . ?
C11 C6 N1 C5 3.5(4) . . . . ?
N1 C2 N3 C4 -0.4(4) . . . . ?
C5 C4 N3 C2 0.7(4) . . . . ?
C11 C6 N7 C8 1.3(4) . . . . ?
N1 C6 N7 C8 178.9(3) . . . . ?
N9 C8 N7 C6 -1.5(5) . . . . ?
N7 C8 N9 C10 0.4(5) . . . . ?
C11 C10 N9 C8 0.9(4) . . . . ?
N12 C10 N9 C8 -176.7(3) . . . . ?
N14 C13 N12 C16 0.3(3) . . . . ?
N14 C13 N12 C10 179.6(2) . . . . ?
C15 C16 N12 C13 0.1(3) . . . . ?
C15 C16 N12 C10 -179.2(3) . . . . ?
N9 C10 N12 C13 -1.6(4) . . . . ?
C11 C10 N12 C13 -179.3(3) . . . . ?
N9 C10 N12 C16 177.6(3) . . . . ?
C11 C10 N12 C16 -0.1(4) . . . . ?
N12 C13 N14 C15 -0.5(4) . . . . ?
C16 C15 N14 C13 0.5(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
N3 H3 O3 0.92(3) 1.90(3) 2.815(3) 175(3) 4_666
N3 H3 O1 0.92(3) 2.44(3) 3.009(4) 120(2) 4_666
N3 H3 N2 0.92(3) 2.53(3) 3.345(4) 149(2) 4_666
N14 H14 O3 0.93(4) 1.88(4) 2.811(3) 172(3) 4_665
N14 H14 O2 0.93(4) 2.32(3) 2.974(3) 127(3) 4_665
N14 H14 N2 0.93(4) 2.44(4) 3.317(3) 156(3) 4_665
O8 H8N O6 1.03(4) 1.45(5) 2.477(3) 174(4) .
O8 H8N N4 1.03(4) 2.25(4) 3.125(4) 142(3) .
O8 H8N O4 1.03(4) 2.40(4) 2.934(3) 112(3) .

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1012940'
#######################################################################
#
#                 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_pm194

_audit_creation_date             2013-11-13T20:03:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N6, Cl4 Zn'
_chemical_formula_sum            'C10 H10 Cl4 N6 Zn'
_chemical_formula_weight         421.41
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C c m 21'
_symmetry_space_group_name_Hall  'C 2c -2c'
_symmetry_Int_Tables_number      36
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z+1/2'
'x, -y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.395(4)
_cell_length_b                   14.021(6)
_cell_length_c                   10.265(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1640.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      6.4
_cell_measurement_theta_max      15
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.149
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.8241

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.044751
_diffrn_orient_matrix_ub_12      0.061299
_diffrn_orient_matrix_ub_13      0.003863
_diffrn_orient_matrix_ub_21      0.075414
_diffrn_orient_matrix_ub_22      0.036448
_diffrn_orient_matrix_ub_23      -0.001862
_diffrn_orient_matrix_ub_31      -0.003149
_diffrn_orient_matrix_ub_32      0.001763
_diffrn_orient_matrix_ub_33      -0.097376
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_number            1506
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.3
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_full        24.95
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             1506
_reflns_number_gt                1246
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0405P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1506
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.042
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.087
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(2)
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Zn1 Zn 0.77018(7) 0.5 1.06775(7) 0.0382(3) Uani 1 2 d S . .
Cl1 Cl 0.78337(18) 0.5 0.84270(18) 0.0395(5) Uani 1 2 d S . .
Cl2 Cl 0.67919(15) 0.63594(13) 1.12195(14) 0.0569(5) Uani 1 1 d . . .
Cl3 Cl 0.95724(19) 0.5 1.1389(2) 0.0556(6) Uani 1 2 d S . .
N1 N 0.4623(4) 0.6728(3) 0.8937(5) 0.0350(12) Uani 1 1 d . . .
C2 C 0.4060(7) 0.7553(4) 0.9089(6) 0.0544(18) Uani 1 1 d . . .
H2 H 0.3344 0.7642 0.9506 0.065 Uiso 1 1 calc R . .
N3 N 0.4702(6) 0.8214(4) 0.8542(7) 0.071(2) Uani 1 1 d . . .
H3 H 0.4519 0.8808 0.851 0.085 Uiso 1 1 calc R . .
C4 C 0.5695(6) 0.7833(5) 0.8032(7) 0.0530(18) Uani 1 1 d . . .
H4 H 0.6297 0.816 0.7614 0.064 Uiso 1 1 calc R . .
C5 C 0.5638(6) 0.6924(5) 0.8244(6) 0.0439(16) Uani 1 1 d . . .
H5 H 0.6188 0.6476 0.7975 0.053 Uiso 1 1 calc R . .
C6 C 0.4156(5) 0.5824(4) 0.9268(5) 0.0334(13) Uani 1 1 d . . .
N7 N 0.3139(4) 0.5852(4) 0.9878(4) 0.0467(13) Uani 1 1 d . . .
C8 C 0.2682(9) 0.5 1.0149(8) 0.048(2) Uani 1 2 d S . .
H8 H 0.1962 0.5 1.0576 0.058 Uiso 1 2 calc SR . .
C9 C 0.4733(7) 0.5 0.8939(8) 0.0352(19) Uani 1 2 d S . .
H9 H 0.5459 0.5 0.8525 0.042 Uiso 1 2 calc SR . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Zn1 Cl2 2.2400(18) 4_565 ?
Zn1 Cl2 2.2400(18) . ?
Zn1 Cl3 2.253(2) . ?
Zn1 Cl1 2.315(2) . ?
N1 C2 1.331(7) . ?
N1 C5 1.386(7) . ?
N1 C6 1.417(7) . ?
C2 N3 1.307(8) . ?
N3 C4 1.357(8) . ?
C4 C5 1.294(9) . ?
C6 N7 1.318(7) . ?
C6 C9 1.371(7) . ?
N7 C8 1.332(6) . ?
C8 N7 1.332(6) 4_565 ?
C9 C6 1.371(7) 4_565 ?

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
Cl2 Zn1 Cl2 116.62(10) 4_565 . ?
Cl2 Zn1 Cl3 110.94(6) 4_565 . ?
Cl2 Zn1 Cl3 110.94(6) . . ?
Cl2 Zn1 Cl1 106.13(5) 4_565 . ?
Cl2 Zn1 Cl1 106.13(5) . . ?
Cl3 Zn1 Cl1 105.19(9) . . ?
C2 N1 C5 106.9(5) . . ?
C2 N1 C6 124.6(5) . . ?
C5 N1 C6 127.9(5) . . ?
N3 C2 N1 107.2(6) . . ?
C2 N3 C4 110.7(6) . . ?
C5 C4 N3 106.3(7) . . ?
C4 C5 N1 108.9(6) . . ?
N7 C6 C9 124.3(5) . . ?
N7 C6 N1 114.7(5) . . ?
C9 C6 N1 121.0(5) . . ?
C6 N7 C8 114.6(6) . . ?
N7 C8 N7 127.4(8) . 4_565 ?
C6 C9 C6 114.8(7) 4_565 . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 1012941'
