# 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_a2901
#TrackingRef 'AR2901_ccdc_deposit.cif'


_audit_creation_date             2013-03-25T13:56:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C9 H6 N4 O2 Zn'
_chemical_formula_weight         267.55
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.4858(3)
_cell_length_b                   18.8309(6)
_cell_length_c                   4.8130(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     950.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2469
_cell_measurement_theta_min      1.9382
_cell_measurement_theta_max      27.9774

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

_exptl_crystal_size_max          0.1981
_exptl_crystal_size_mid          0.0784
_exptl_crystal_size_min          0.0556
_exptl_crystal_density_diffrn    1.87
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0328
-1 -1 0 0.0228
0 0 -1 0.099
0 0 1 0.099
0 1 0 0.0346
0 -1 0 0.0346
1 -1 0 0.0329
-1 1 0 0.0329

_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.975

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_ub_11      -0.0143003
_diffrn_orient_matrix_ub_12      -0.0368036
_diffrn_orient_matrix_ub_13      -0.001562
_diffrn_orient_matrix_ub_21      0.0657294
_diffrn_orient_matrix_ub_22      -0.0079102
_diffrn_orient_matrix_ub_23      -0.0156715
_diffrn_orient_matrix_ub_31      0.0067716
_diffrn_orient_matrix_ub_32      -0.0012437
_diffrn_orient_matrix_ub_33      0.1466175
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_number            5822
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.04
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.95
_reflns_number_total             2031
_reflns_number_gt                1835
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# 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)+(0.0397P)²+0.1362P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_restrained_S_all      1.08
_refine_ls_shift/su_max          0.001
_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   -0.04(2)
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
# 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'
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
C18 C 0.8568(3) 0.41181(16) 0.7901(10) 0.0263(7) Uani 1 1 d . . .
C17 C 0.7812(4) 0.46730(19) 0.9416(8) 0.0360(9) Uani 1 1 d . . .
H17A H 0.8285 0.4808 1.1066 0.043 Uiso 1 1 calc R . .
H17B H 0.702 0.4458 1.0031 0.043 Uiso 1 1 calc R . .
C13 C 0.7491(3) 0.53387(16) 0.7833(8) 0.0284(7) Uani 1 1 d . . .
C12 C 0.8085(3) 0.59748(17) 0.8508(8) 0.0272(8) Uani 1 1 d . . .
H12 H 0.8703 0.5982 0.9895 0.033 Uiso 1 1 calc R . .
C11 C 0.7772(4) 0.66004(17) 0.7146(7) 0.0259(8) Uani 1 1 d . . .
C16 C 0.6861(4) 0.66000(18) 0.5065(8) 0.0321(9) Uani 1 1 d . . .
H16 H 0.666 0.7017 0.4127 0.039 Uiso 1 1 calc R . .
C15 C 0.6251(4) 0.5967(2) 0.4396(9) 0.0358(9) Uani 1 1 d . . .
H15 H 0.5629 0.5962 0.3019 0.043 Uiso 1 1 calc R . .
C14 C 0.6563(4) 0.53474(19) 0.5765(9) 0.0328(8) Uani 1 1 d . . .
H14 H 0.6146 0.4928 0.5299 0.039 Uiso 1 1 calc R . .
C5 C 0.8385(3) 0.72618(15) 0.8141(11) 0.0249(6) Uani 1 1 d . . .
N1 N 0.7820(3) 0.78766(14) 0.8655(7) 0.0296(8) Uani 1 1 d . . .
N2 N 0.8730(3) 0.83122(16) 0.9735(9) 0.0393(9) Uani 1 1 d . . .
N3 N 0.9795(3) 0.79717(17) 0.9807(8) 0.0390(8) Uani 1 1 d . . .
N4 N 0.9626(3) 0.73112(15) 0.8790(6) 0.0285(8) Uani 1 1 d . . .
O1 O 0.8977(3) 0.35853(15) 0.9191(6) 0.0340(6) Uani 1 1 d . . .
O2 O 0.8745(2) 0.41882(13) 0.5336(5) 0.0288(6) Uani 1 1 d . . .
Zn1 Zn 0.60971(3) 0.831415(17) 0.81444(13) 0.02440(12) Uani 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
C18 O2 1.255(6) . ?
C18 O1 1.255(4) . ?
C18 C17 1.501(5) . ?
C17 C13 1.505(5) . ?
C13 C12 1.389(5) . ?
C13 C14 1.392(5) . ?
C12 C11 1.388(5) . ?
C11 C16 1.384(5) . ?
C11 C5 1.481(4) . ?
C16 C15 1.390(5) . ?
C15 C14 1.380(5) . ?
C5 N1 1.324(4) . ?
C5 N4 1.342(4) . ?
N1 N2 1.361(4) . ?
N1 Zn1 2.001(3) . ?
N2 N3 1.287(4) . ?
N3 N4 1.348(4) . ?
N4 Zn1 1.965(3) 4_565 ?
O1 Zn1 1.972(3) 3_645 ?
O2 Zn1 1.962(3) 3_644 ?
Zn1 O2 1.962(3) 3_655 ?
Zn1 N4 1.965(3) 4_465 ?
Zn1 O1 1.972(3) 3_654 ?

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
O2 C18 O1 121.3(4) . . ?
O2 C18 C17 118.9(3) . . ?
O1 C18 C17 119.8(4) . . ?
C18 C17 C13 116.9(3) . . ?
C12 C13 C14 118.1(3) . . ?
C12 C13 C17 120.0(4) . . ?
C14 C13 C17 121.9(3) . . ?
C11 C12 C13 121.0(4) . . ?
C16 C11 C12 120.3(3) . . ?
C16 C11 C5 122.3(3) . . ?
C12 C11 C5 117.3(4) . . ?
C11 C16 C15 119.1(3) . . ?
C14 C15 C16 120.3(4) . . ?
C15 C14 C13 121.2(4) . . ?
N1 C5 N4 109.2(3) . . ?
N1 C5 C11 127.0(3) . . ?
N4 C5 C11 123.7(3) . . ?
C5 N1 N2 106.6(3) . . ?
C5 N1 Zn1 137.8(2) . . ?
N2 N1 Zn1 115.6(2) . . ?
N3 N2 N1 108.5(3) . . ?
N2 N3 N4 109.6(3) . . ?
C5 N4 N3 106.0(3) . . ?
C5 N4 Zn1 133.1(2) . 4_565 ?
N3 N4 Zn1 120.5(2) . 4_565 ?
C18 O1 Zn1 132.2(3) . 3_645 ?
C18 O2 Zn1 116.9(2) . 3_644 ?
O2 Zn1 N4 118.94(12) 3_655 4_465 ?
O2 Zn1 O1 107.75(11) 3_655 3_654 ?
N4 Zn1 O1 106.09(11) 4_465 3_654 ?
O2 Zn1 N1 101.73(11) 3_655 . ?
N4 Zn1 N1 116.27(12) 4_465 . ?
O1 Zn1 N1 105.10(13) 3_654 . ?
_database_code_depnum_ccdc_archive 'CCDC 930950'
#######################################################################
#
#                 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_a2903
#TrackingRef 'AR2903_ccdc_deposit.cif'


_audit_creation_date             2013-03-25T14:02:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C9 H6 N4 O2 Zn'
_chemical_formula_weight         267.55
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   18.5081(5)
_cell_length_b                   4.82300(10)
_cell_length_c                   10.9635(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     978.65(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1541
_cell_measurement_theta_min      1.8537
_cell_measurement_theta_max      28.054

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

_exptl_crystal_size_max          0.3178
_exptl_crystal_size_mid          0.2151
_exptl_crystal_size_min          0.0437
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0219
-1 0 0 0.0219
0 1 0 0.1033
0 -1 0 0.1216
3 0 5 0.0836
-3 -1 -4 0.0669

_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_T_max  1.086

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_ub_11      -0.0323604
_diffrn_orient_matrix_ub_12      -0.0655297
_diffrn_orient_matrix_ub_13      0.0192136
_diffrn_orient_matrix_ub_21      0.0156796
_diffrn_orient_matrix_ub_22      -0.131647
_diffrn_orient_matrix_ub_23      -0.0115522
_diffrn_orient_matrix_ub_31      0.0132324
_diffrn_orient_matrix_ub_32      -0.0042167
_diffrn_orient_matrix_ub_33      0.0606785
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_number            4785
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.2
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.923
_reflns_number_total             1955
_reflns_number_gt                1510
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# 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)+(0.0166P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1955
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.058
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_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   -0.01(2)
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
# 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'
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
C5 C 0.2221(2) 0.0281(8) 0.2726(5) 0.0209(11) Uani 1 1 d . . .
C11 C 0.1579(2) 0.1768(9) 0.3180(4) 0.0204(11) Uani 1 1 d . . .
C16 C 0.1621(2) 0.3684(10) 0.4110(5) 0.0314(13) Uani 1 1 d . . .
H16 H 0.2063 0.4033 0.4483 0.038 Uiso 1 1 calc R . .
C15 C 0.1015(2) 0.5081(10) 0.4488(5) 0.0334(14) Uani 1 1 d . . .
H15 H 0.1052 0.6348 0.5125 0.04 Uiso 1 1 calc R . .
C14 C 0.0349(2) 0.4646(10) 0.3944(5) 0.0278(12) Uani 1 1 d . . .
C13 C 0.0303(2) 0.2699(10) 0.3017(5) 0.0278(12) Uani 1 1 d . . .
H13 H -0.0138 0.237 0.2638 0.033 Uiso 1 1 calc R . .
C12 C 0.0906(2) 0.1253(10) 0.2657(5) 0.0257(12) Uani 1 1 d . . .
H12 H 0.0864 -0.0093 0.2053 0.031 Uiso 1 1 calc R . .
C17 C -0.0302(2) 0.6313(10) 0.4318(5) 0.0326(13) Uani 1 1 d . . .
H17A H -0.0467 0.7351 0.3613 0.039 Uiso 1 1 calc R . .
H17B H -0.015 0.7649 0.4928 0.039 Uiso 1 1 calc R . .
N3 N 0.2957(2) -0.1841(10) 0.1528(4) 0.0427(12) Uani 1 1 d . . .
N2 N 0.3243(2) -0.1837(10) 0.2595(4) 0.0401(12) Uani 1 1 d . . .
C18 C -0.0937(2) 0.4723(8) 0.4824(6) 0.0218(14) Uani 1 1 d . . .
N1 N 0.2786(3) -0.0492(11) 0.3395(5) 0.0265(13) Uani 1 1 d . . .
N4 N 0.2312(3) -0.0527(10) 0.1573(5) 0.0245(12) Uani 1 1 d . . .
O11 O -0.08810(13) 0.2134(5) 0.4939(5) 0.0234(7) Uani 1 1 d . . .
O12 O -0.15154(13) 0.5987(5) 0.5044(5) 0.0257(7) Uani 1 1 d . . .
Zn1 Zn 0.17769(2) 0.00413(10) 0.00374(12) 0.02014(13) Uani 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
C5 N1 1.330(7) . ?
C5 N4 1.334(7) . ?
C5 C11 1.474(6) . ?
C11 C16 1.378(7) . ?
C11 C12 1.394(6) . ?
C16 C15 1.373(6) . ?
C15 C14 1.386(6) . ?
C14 C13 1.386(7) . ?
C14 C17 1.505(6) . ?
C13 C12 1.373(6) . ?
C17 C18 1.510(6) . ?
N3 N2 1.285(5) . ?
N3 N4 1.352(6) . ?
N2 N1 1.379(6) . ?
C18 O12 1.255(4) . ?
C18 O11 1.259(5) . ?
N1 Zn1 1.991(5) 3 ?
N4 Zn1 1.973(6) . ?
O11 Zn1 1.965(2) 2 ?
O12 Zn1 1.976(2) 2_565 ?
Zn1 O11 1.965(2) 2_554 ?
Zn1 O12 1.976(2) 2_564 ?
Zn1 N1 1.991(5) 3_554 ?

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 C5 N4 110.0(4) . . ?
N1 C5 C11 125.7(5) . . ?
N4 C5 C11 124.3(4) . . ?
C16 C11 C12 118.3(4) . . ?
C16 C11 C5 122.0(4) . . ?
C12 C11 C5 119.7(4) . . ?
C15 C16 C11 120.4(5) . . ?
C16 C15 C14 121.5(5) . . ?
C15 C14 C13 118.2(4) . . ?
C15 C14 C17 120.9(5) . . ?
C13 C14 C17 120.9(4) . . ?
C12 C13 C14 120.4(4) . . ?
C13 C12 C11 121.1(4) . . ?
C14 C17 C18 116.9(4) . . ?
N2 N3 N4 109.2(4) . . ?
N3 N2 N1 109.1(4) . . ?
O12 C18 O11 122.2(4) . . ?
O12 C18 C17 119.2(4) . . ?
O11 C18 C17 118.4(4) . . ?
C5 N1 N2 105.3(5) . . ?
C5 N1 Zn1 141.4(4) . 3 ?
N2 N1 Zn1 112.7(4) . 3 ?
C5 N4 N3 106.5(5) . . ?
C5 N4 Zn1 134.8(4) . . ?
N3 N4 Zn1 118.5(4) . . ?
C18 O11 Zn1 117.7(2) . 2 ?
C18 O12 Zn1 132.8(3) . 2_565 ?
O11 Zn1 N4 113.3(2) 2_554 . ?
O11 Zn1 O12 108.13(10) 2_554 2_564 ?
N4 Zn1 O12 104.7(2) . 2_564 ?
O11 Zn1 N1 103.0(2) 2_554 3_554 ?
N4 Zn1 N1 123.37(15) . 3_554 ?
O12 Zn1 N1 103.2(2) 2_564 3_554 ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


_database_code_depnum_ccdc_archive 'CCDC 930951'
