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

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1451196'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N5 O3'
_chemical_formula_sum            'C9 H7 N5 O3'
_chemical_formula_weight         233.20

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.3288(4)
_cell_length_b                   18.3034(13)
_cell_length_c                   10.3561(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.819(7)
_cell_angle_gamma                90
_cell_volume                     1006.52(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1695
_cell_measurement_theta_min      2.9690
_cell_measurement_theta_max      25.6764

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86016
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '95 images, ΔΦ 2.0°'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6795
_diffrn_reflns_av_unetI/netI     0.1103
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.975
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1826
_reflns_number_gt                1105
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;




_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1826
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1594(6) 0.78982(16) -0.0077(3) 0.0342(8) Uani 1 1 d . . . . .
N2 N 0.0019(6) 0.83773(16) 0.0621(3) 0.0376(8) Uani 1 1 d . . . . .
C3 C 0.1841(7) 0.79865(17) 0.1158(4) 0.0332(9) Uani 1 1 d . . . . .
H3 H 0.3222 0.8174 0.1698 0.040 Uiso 1 1 calc R U . . .
N4 N 0.1503(5) 0.72692(14) 0.0842(3) 0.0261(7) Uani 1 1 d . . . . .
C5 C -0.0646(7) 0.72467(18) 0.0082(4) 0.0318(9) Uani 1 1 d . . . . .
H5 H -0.1381 0.6815 -0.0291 0.038 Uiso 1 1 calc R U . . .
N6 N 0.2873(5) 0.66354(14) 0.1172(3) 0.0291(7) Uani 1 1 d . . . . .
C7 C 0.4885(6) 0.67101(18) 0.1912(3) 0.0271(8) Uani 1 1 d . . . . .
H7 H 0.5379 0.7182 0.2217 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6437(7) 0.60810(17) 0.2297(3) 0.0276(8) Uani 1 1 d . . . . .
C9 C 0.8649(6) 0.61914(17) 0.3117(3) 0.0263(8) Uani 1 1 d . . . . .
C10 C 1.0186(7) 0.55972(18) 0.3498(3) 0.0318(9) Uani 1 1 d . . . . .
H10 H 1.1678 0.5672 0.4051 0.038 Uiso 1 1 calc R U . . .
C11 C 0.9538(7) 0.49035(18) 0.3072(3) 0.0314(9) Uani 1 1 d . . . . .
H11 H 1.0591 0.4499 0.3315 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7329(7) 0.48031(17) 0.2284(3) 0.0275(8) Uani 1 1 d . . . . .
C13 C 0.5780(6) 0.53772(18) 0.1893(3) 0.0283(9) Uani 1 1 d . . . . .
H13 H 0.4277 0.5293 0.1353 0.034 Uiso 1 1 calc R U . . .
O14 O 0.9195(5) 0.68772(12) 0.3482(2) 0.0343(7) Uani 1 1 d . . . . .
H14 H 1.0566 0.6884 0.3946 0.051 Uiso 1 1 calc R U . . .
N15 N 0.6613(6) 0.40710(15) 0.1851(3) 0.0314(8) Uani 1 1 d . . . . .
O16 O 0.4474(5) 0.39777(13) 0.1328(3) 0.0410(7) Uani 1 1 d . . . . .
O17 O 0.8169(5) 0.35752(12) 0.2036(3) 0.0398(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.300(4) . ?
N1 N2 1.388(4) . ?
N2 C3 1.294(4) . ?
C3 N4 1.362(4) . ?
C3 H3 0.9500 . ?
N4 C5 1.335(4) . ?
N4 N6 1.398(4) . ?
C5 H5 0.9500 . ?
N6 C7 1.272(4) . ?
C7 C8 1.454(5) . ?
C7 H7 0.9500 . ?
C8 C13 1.390(5) . ?
C8 C9 1.408(5) . ?
C9 O14 1.336(4) . ?
C9 C10 1.398(5) . ?
C10 C11 1.378(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(5) . ?
C12 N15 1.454(4) . ?
C13 H13 0.9500 . ?
O14 H14 0.8400 . ?
N15 O16 1.232(4) . ?
N15 O17 1.233(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
C5 N1 N2 107.3(3) . . ?
C3 N2 N1 106.5(3) . . ?
N2 C3 N4 110.5(3) . . ?
N2 C3 H3 124.7 . . ?
N4 C3 H3 124.7 . . ?
C5 N4 C3 105.1(3) . . ?
C5 N4 N6 121.6(3) . . ?
C3 N4 N6 133.3(3) . . ?
N1 C5 N4 110.6(3) . . ?
N1 C5 H5 124.7 . . ?
N4 C5 H5 124.7 . . ?
C7 N6 N4 117.1(3) . . ?
N6 C7 C8 120.8(3) . . ?
N6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 C7 121.9(3) . . ?
C9 C8 C7 118.7(3) . . ?
O14 C9 C10 122.9(3) . . ?
O14 C9 C8 117.2(3) . . ?
C10 C9 C8 120.0(3) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 N15 118.6(3) . . ?
C11 C12 N15 119.4(3) . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C9 O14 H14 109.5 . . ?
O16 N15 O17 123.5(3) . . ?
O16 N15 C12 118.2(3) . . ?
O17 N15 C12 118.3(3) . . ?

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 N2 C3 0.0(4) . . . . ?
N1 N2 C3 N4 0.2(4) . . . . ?
N2 C3 N4 C5 -0.3(4) . . . . ?
N2 C3 N4 N6 -179.1(3) . . . . ?
N2 N1 C5 N4 -0.1(4) . . . . ?
C3 N4 C5 N1 0.2(4) . . . . ?
N6 N4 C5 N1 179.2(3) . . . . ?
C5 N4 N6 C7 -179.3(3) . . . . ?
C3 N4 N6 C7 -0.6(6) . . . . ?
N4 N6 C7 C8 -179.5(3) . . . . ?
N6 C7 C8 C13 -0.9(6) . . . . ?
N6 C7 C8 C9 179.9(3) . . . . ?
C13 C8 C9 O14 -179.8(3) . . . . ?
C7 C8 C9 O14 -0.6(5) . . . . ?
C13 C8 C9 C10 1.2(5) . . . . ?
C7 C8 C9 C10 -179.7(3) . . . . ?
O14 C9 C10 C11 -179.0(3) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 -1.2(5) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C10 C11 C12 N15 -178.9(3) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
N15 C12 C13 C8 -179.9(3) . . . . ?
C9 C8 C13 C12 -1.2(5) . . . . ?
C7 C8 C13 C12 179.7(3) . . . . ?
C13 C12 N15 O16 -11.4(5) . . . . ?
C11 C12 N15 O16 168.7(3) . . . . ?
C13 C12 N15 O17 169.3(3) . . . . ?
C11 C12 N15 O17 -10.6(5) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.068

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1451197'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_3                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off to 1.00A was imposed beyond which the data
quality in terms of of I/sigma and Rint.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N4 O2'
_chemical_formula_sum            'C9 H8 N4 O2'
_chemical_formula_weight         204.19

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.8474(12)
_cell_length_b                   21.040(4)
_cell_length_c                   7.5567(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.25(2)
_cell_angle_gamma                90
_cell_volume                     887.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    538
_cell_measurement_theta_min      2.8780
_cell_measurement_theta_max      20.4400

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.03731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?





_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '175 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1626
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.984
_diffrn_reflns_theta_max         20.834
_diffrn_reflns_theta_full        20.834
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             1626
_reflns_number_gt                805
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;





_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1626
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0848
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0235(16) 0.1321(4) 0.0993(12) 0.071(3) Uani 1 1 d . . . . .
N2 N 0.0679(16) 0.1948(4) 0.1621(12) 0.072(3) Uani 1 1 d . . . . .
C3 C 0.285(2) 0.1979(5) 0.2730(15) 0.071(4) Uani 1 1 d . . . . .
H3 H 0.3579 0.2342 0.3347 0.085 Uiso 1 1 calc R U . . .
N4 N 0.3873(14) 0.1397(4) 0.2843(12) 0.060(2) Uani 1 1 d . . . . .
C5 C 0.224(2) 0.1008(5) 0.1783(15) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.2475 0.0578 0.1620 0.082 Uiso 1 1 calc R U . . .
N6 N 0.6067(16) 0.1149(4) 0.3893(13) 0.066(3) Uani 1 1 d . . . . .
C7 C 0.767(2) 0.1544(5) 0.4773(16) 0.072(3) Uani 1 1 d . . . . .
H7 H 0.7360 0.1978 0.4647 0.086 Uiso 1 1 calc R U . . .
C8 C 0.9994(18) 0.1323(5) 0.5975(14) 0.059(3) Uani 1 1 d . . . . .
C9 C 1.187(2) 0.1732(5) 0.6716(15) 0.068(3) Uani 1 1 d . . . . .
C10 C 1.403(2) 0.1504(5) 0.7743(16) 0.064(3) Uani 1 1 d . . . . .
H10 H 1.5306 0.1781 0.8226 0.077 Uiso 1 1 calc R U . . .
C11 C 1.4325(18) 0.0870(5) 0.8059(15) 0.065(3) Uani 1 1 d . . . . .
C12 C 1.251(2) 0.0457(5) 0.7356(15) 0.076(4) Uani 1 1 d . . . . .
H12 H 1.2749 0.0023 0.7567 0.092 Uiso 1 1 calc R U . . .
C13 C 1.033(2) 0.0676(5) 0.6341(15) 0.073(4) Uani 1 1 d . . . . .
H13 H 0.9062 0.0395 0.5891 0.088 Uiso 1 1 calc R U . . .
O14 O 1.1542(12) 0.2365(3) 0.6295(10) 0.080(3) Uani 1 1 d . . . . .
H14 H 1.2781 0.2559 0.6795 0.121 Uiso 1 1 calc R U . . .
O15 O 1.6453(13) 0.0597(3) 0.9063(11) 0.090(3) Uani 1 1 d . . . . .
H15 H 1.7466 0.0875 0.9429 0.135 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.322(12) . ?
N1 N2 1.400(11) . ?
N2 C3 1.298(12) . ?
C3 N4 1.355(11) . ?
C3 H3 0.9300 . ?
N4 C5 1.330(11) . ?
N4 N6 1.395(10) . ?
C5 H5 0.9300 . ?
N6 C7 1.283(12) . ?
C7 C8 1.467(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(13) . ?
C8 C13 1.391(13) . ?
C9 C10 1.359(13) . ?
C9 O14 1.371(11) . ?
C10 C11 1.357(13) . ?
C10 H10 0.9300 . ?
C11 O15 1.376(11) . ?
C11 C12 1.354(13) . ?
C12 C13 1.358(13) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
O14 H14 0.8200 . ?
O15 H15 0.8200 . ?

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
C5 N1 N2 105.4(8) . . ?
C3 N2 N1 108.3(9) . . ?
N2 C3 N4 108.9(10) . . ?
N2 C3 H3 125.5 . . ?
N4 C3 H3 125.5 . . ?
C5 N4 C3 107.0(9) . . ?
C5 N4 N6 119.1(8) . . ?
C3 N4 N6 133.6(9) . . ?
N1 C5 N4 110.4(9) . . ?
N1 C5 H5 124.8 . . ?
N4 C5 H5 124.8 . . ?
C7 N6 N4 117.3(9) . . ?
N6 C7 C8 121.0(10) . . ?
N6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C13 118.8(9) . . ?
C9 C8 C7 122.3(10) . . ?
C13 C8 C7 118.9(10) . . ?
C10 C9 O14 121.3(10) . . ?
C10 C9 C8 120.5(10) . . ?
O14 C9 C8 118.1(10) . . ?
C11 C10 C9 119.6(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 O15 123.5(10) . . ?
C10 C11 C12 121.3(10) . . ?
O15 C11 C12 115.2(10) . . ?
C13 C12 C11 120.0(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 119.8(10) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C9 O14 H14 109.5 . . ?
C11 O15 H15 109.5 . . ?

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 N2 C3 -0.5(12) . . . . ?
N1 N2 C3 N4 0.8(13) . . . . ?
N2 C3 N4 C5 -0.9(13) . . . . ?
N2 C3 N4 N6 -175.2(11) . . . . ?
N2 N1 C5 N4 0.0(13) . . . . ?
C3 N4 C5 N1 0.5(14) . . . . ?
N6 N4 C5 N1 175.9(9) . . . . ?
C5 N4 N6 C7 174.1(11) . . . . ?
C3 N4 N6 C7 -12.0(17) . . . . ?
N4 N6 C7 C8 177.3(9) . . . . ?
N6 C7 C8 C9 170.2(12) . . . . ?
N6 C7 C8 C13 -8.2(17) . . . . ?
C13 C8 C9 C10 1.8(17) . . . . ?
C7 C8 C9 C10 -176.5(11) . . . . ?
C13 C8 C9 O14 177.9(10) . . . . ?
C7 C8 C9 O14 -0.4(16) . . . . ?
O14 C9 C10 C11 -176.9(11) . . . . ?
C8 C9 C10 C11 -0.9(18) . . . . ?
C9 C10 C11 O15 179.2(11) . . . . ?
C9 C10 C11 C12 0.6(19) . . . . ?
C10 C11 C12 C13 -1.3(19) . . . . ?
O15 C11 C12 C13 -179.9(11) . . . . ?
C11 C12 C13 C8 2.1(18) . . . . ?
C9 C8 C13 C12 -2.4(17) . . . . ?
C7 C8 C13 C12 176.0(11) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.072

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1451198'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 N4 O2'
_chemical_formula_sum            'C10 H10 N4 O2'
_chemical_formula_weight         218.22

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.9241(13)
_cell_length_b                   19.9241(13)
_cell_length_c                   5.1153(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2030.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      2.0402
_cell_measurement_theta_max      25.2838

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.96813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '68 images, ΔΦ 2.4° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11261
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1798
_reflns_number_gt                1285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;






_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.9052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1798
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40042(13) 0.63811(12) -0.3220(4) 0.0396(6) Uani 1 1 d . . . . .
N2 N 0.34919(13) 0.68012(13) -0.2383(5) 0.0448(7) Uani 1 1 d . . . . .
C3 C 0.37309(15) 0.71529(14) -0.0442(6) 0.0395(7) Uani 1 1 d . . . . .
H3 H 0.3490 0.7473 0.0489 0.047 Uiso 1 1 calc R U . . .
N4 N 0.43780(11) 0.69862(11) 0.0027(4) 0.0318(6) Uani 1 1 d . . . . .
C5 C 0.45210(16) 0.65073(14) -0.1752(5) 0.0386(7) Uani 1 1 d . . . . .
H5 H 0.4935 0.6295 -0.1908 0.046 Uiso 1 1 calc R U . . .
N6 N 0.48747(11) 0.72385(11) 0.1707(4) 0.0343(6) Uani 1 1 d . . . . .
C7 C 0.46856(14) 0.76606(13) 0.3414(5) 0.0311(7) Uani 1 1 d . . . . .
H7 H 0.4234 0.7772 0.3566 0.037 Uiso 1 1 calc R U . . .
C8 C 0.51825(14) 0.79703(13) 0.5143(5) 0.0290(6) Uani 1 1 d . . . . .
C9 C 0.49649(14) 0.84038(13) 0.7108(5) 0.0296(6) Uani 1 1 d . . . . .
C10 C 0.54385(14) 0.87289(14) 0.8705(5) 0.0324(7) Uani 1 1 d . . . . .
C11 C 0.61117(16) 0.86054(15) 0.8366(6) 0.0417(8) Uani 1 1 d . . . . .
H11 H 0.6424 0.8814 0.9443 0.050 Uiso 1 1 calc R U . . .
C12 C 0.63261(15) 0.81692(16) 0.6418(6) 0.0454(8) Uani 1 1 d . . . . .
H12 H 0.6782 0.8086 0.6199 0.054 Uiso 1 1 calc R U . . .
C13 C 0.58689(15) 0.78609(14) 0.4817(6) 0.0385(7) Uani 1 1 d . . . . .
H13 H 0.6018 0.7576 0.3500 0.046 Uiso 1 1 calc R U . . .
O14 O 0.43048(10) 0.85115(11) 0.7435(4) 0.0416(5) Uani 1 1 d . . . . .
H14 H 0.4241 0.8701 0.8837 0.062 Uiso 1 1 calc R U . . .
O15 O 0.51624(10) 0.91519(10) 1.0500(4) 0.0464(6) Uani 1 1 d . . . . .
C16 C 0.55970(17) 0.95168(15) 1.2179(5) 0.0475(9) Uani 1 1 d . . . . .
H16A H 0.5871 0.9209 1.3152 0.071 Uiso 1 1 calc R U . . .
H16B H 0.5335 0.9782 1.3366 0.071 Uiso 1 1 calc R U . . .
H16C H 0.5879 0.9806 1.1154 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.299(4) . ?
N1 N2 1.388(3) . ?
N2 C3 1.305(3) . ?
C3 N4 1.353(3) . ?
C3 H3 0.9300 . ?
N4 C5 1.349(3) . ?
N4 N6 1.404(3) . ?
C5 H5 0.9300 . ?
N6 C7 1.270(3) . ?
C7 C8 1.464(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(4) . ?
C8 C13 1.395(4) . ?
C9 O14 1.343(3) . ?
C9 C10 1.406(4) . ?
C10 O15 1.362(3) . ?
C10 C11 1.375(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
O14 H14 0.8200 . ?
O15 C16 1.420(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C5 N1 N2 106.7(2) . . ?
C3 N2 N1 106.9(2) . . ?
N2 C3 N4 110.5(3) . . ?
N2 C3 H3 124.7 . . ?
N4 C3 H3 124.7 . . ?
C5 N4 C3 104.8(2) . . ?
C5 N4 N6 121.2(2) . . ?
C3 N4 N6 133.8(2) . . ?
N1 C5 N4 111.1(3) . . ?
N1 C5 H5 124.5 . . ?
N4 C5 H5 124.5 . . ?
C7 N6 N4 116.7(2) . . ?
N6 C7 C8 119.6(3) . . ?
N6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 C7 119.1(2) . . ?
C13 C8 C7 121.7(2) . . ?
O14 C9 C8 119.5(2) . . ?
O14 C9 C10 120.8(2) . . ?
C8 C9 C10 119.7(3) . . ?
O15 C10 C11 126.1(2) . . ?
O15 C10 C9 113.9(2) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C9 O14 H14 109.5 . . ?
C10 O15 C16 118.6(2) . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 N2 C3 -0.4(3) . . . . ?
N1 N2 C3 N4 0.3(3) . . . . ?
N2 C3 N4 C5 -0.1(3) . . . . ?
N2 C3 N4 N6 174.3(3) . . . . ?
N2 N1 C5 N4 0.4(3) . . . . ?
C3 N4 C5 N1 -0.2(3) . . . . ?
N6 N4 C5 N1 -175.5(2) . . . . ?
C5 N4 N6 C7 -176.2(2) . . . . ?
C3 N4 N6 C7 10.2(4) . . . . ?
N4 N6 C7 C8 -176.9(2) . . . . ?
N6 C7 C8 C9 -176.4(2) . . . . ?
N6 C7 C8 C13 5.9(4) . . . . ?
C13 C8 C9 O14 -180.0(2) . . . . ?
C7 C8 C9 O14 2.2(4) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
C7 C8 C9 C10 -177.1(2) . . . . ?
O14 C9 C10 O15 -0.9(4) . . . . ?
C8 C9 C10 O15 178.3(2) . . . . ?
O14 C9 C10 C11 179.1(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
O15 C10 C11 C12 -178.8(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C8 -1.1(4) . . . . ?
C9 C8 C13 C12 0.6(4) . . . . ?
C7 C8 C13 C12 178.4(3) . . . . ?
C11 C10 O15 C16 1.2(4) . . . . ?
C9 C10 O15 C16 -178.7(2) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1451199'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_5                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off was imposed during integration/refinement as
the recorded data beyond 1.04A was too poor in terms of I/sigma
and Rint.
;
_vrf_PLAT089_5                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.57 Note  
RESPONSE: see above, the low data/parameter ratio is a direct result of
the data cut-off to 1.04A.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 Cl N4 O'
_chemical_formula_sum            'C9 H7 Cl N4 O'
_chemical_formula_weight         222.64

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.7737(14)
_cell_length_b                   14.259(5)
_cell_length_c                   8.993(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.23(4)
_cell_angle_gamma                90
_cell_volume                     474.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    778
_cell_measurement_theta_min      2.3043
_cell_measurement_theta_max      20.7685

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.378
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_T_min  0.73541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?





_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '61 images, ΔΦ 3.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            849
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.715
_diffrn_reflns_theta_max         19.980
_diffrn_reflns_theta_full        19.980
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             849
_reflns_number_gt                737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    0.905

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;




_refine_special_details          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0943P)²+1.7828P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         849
_refine_ls_number_parameters     126
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2008
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.435(5) 0.0362(13) 1.080(2) 0.039(5) Uani 1 1 d . U . . .
N2 N 1.238(5) -0.0262(12) 0.974(2) 0.035(4) Uani 1 1 d . U . . .
C3 C 1.046(6) 0.0281(15) 0.868(2) 0.030(5) Uani 1 1 d . U . . .
H3 H 0.8831 0.0045 0.7824 0.036 Uiso 1 1 calc R U . . .
N4 N 1.105(4) 0.1178(12) 0.8951(18) 0.023(4) Uani 1 1 d . U . . .
C5 C 1.352(5) 0.1211(16) 1.032(2) 0.030(5) Uani 1 1 d . U . . .
H5 H 1.4456 0.1768 1.0832 0.037 Uiso 1 1 calc R U . . .
N6 N 0.959(4) 0.1981(11) 0.823(2) 0.032(4) Uani 1 1 d . U . . .
C7 C 0.769(5) 0.1925(15) 0.686(2) 0.027(5) Uani 1 1 d . U . . .
H7 H 0.7412 0.1336 0.6361 0.032 Uiso 1 1 calc R U . . .
C8 C 0.603(3) 0.2736(8) 0.6115(13) 0.025(5) Uani 1 1 d G U . . .
C9 C 0.619(3) 0.3616(9) 0.6790(11) 0.029(5) Uani 1 1 d G U . . .
C10 C 0.451(4) 0.4379(7) 0.5980(14) 0.026(5) Uani 1 1 d G U . . .
H10 H 0.4622 0.4980 0.6441 0.031 Uiso 1 1 calc R U . . .
C11 C 0.267(4) 0.4261(8) 0.4495(14) 0.028(5) Uani 1 1 d G U . . .
H11 H 0.1527 0.4782 0.3941 0.034 Uiso 1 1 calc R U . . .
C12 C 0.251(4) 0.3381(10) 0.3820(11) 0.024(5) Uani 1 1 d G U . . .
C13 C 0.419(3) 0.2619(8) 0.4629(13) 0.030(5) Uani 1 1 d G U . . .
H13 H 0.4077 0.2017 0.4168 0.036 Uiso 1 1 calc R U . . .
O14 O 0.792(4) 0.3802(10) 0.8207(14) 0.035(4) Uani 1 1 d . . . . .
H14 H 0.8887 0.3309 0.8608 0.053 Uiso 1 1 calc R U . . .
Cl15 Cl 0.0085(14) 0.3248(4) 0.1949(7) 0.0366(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.30(3) . ?
N1 N2 1.41(2) . ?
N2 C3 1.33(2) . ?
C3 N4 1.31(3) . ?
C3 H3 0.9500 . ?
N4 N6 1.37(2) . ?
N4 C5 1.40(2) . ?
C5 H5 0.9500 . ?
N6 C7 1.30(3) . ?
C7 C8 1.42(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 O14 1.341(15) . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C13 1.3900 . ?
C12 Cl15 1.762(10) . ?
C13 H13 0.9500 . ?
O14 H14 0.8400 . ?

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
C5 N1 N2 107.5(16) . . ?
C3 N2 N1 105.1(15) . . ?
N4 C3 N2 112.8(18) . . ?
N4 C3 H3 123.6 . . ?
N2 C3 H3 123.6 . . ?
C3 N4 N6 133.5(17) . . ?
C3 N4 C5 104.7(18) . . ?
N6 N4 C5 121.6(17) . . ?
N1 C5 N4 110(2) . . ?
N1 C5 H5 125.1 . . ?
N4 C5 H5 125.1 . . ?
C7 N6 N4 119.2(17) . . ?
N6 C7 C8 120.7(19) . . ?
N6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 123.3(12) . . ?
C13 C8 C7 116.7(12) . . ?
O14 C9 C8 124.4(10) . . ?
O14 C9 C10 115.6(10) . . ?
C8 C9 C10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 Cl15 121.0(8) . . ?
C11 C12 Cl15 119.0(7) . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C9 O14 H14 109.5 . . ?

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 N2 C3 0(2) . . . . ?
N1 N2 C3 N4 1(3) . . . . ?
N2 C3 N4 N6 -176.3(19) . . . . ?
N2 C3 N4 C5 -1(2) . . . . ?
N2 N1 C5 N4 -1(2) . . . . ?
C3 N4 C5 N1 1(2) . . . . ?
N6 N4 C5 N1 176.9(18) . . . . ?
C3 N4 N6 C7 -15(3) . . . . ?
C5 N4 N6 C7 170.7(17) . . . . ?
N4 N6 C7 C8 177.4(15) . . . . ?
N6 C7 C8 C9 -2(2) . . . . ?
N6 C7 C8 C13 177.1(14) . . . . ?
C13 C8 C9 O14 -179.2(13) . . . . ?
C7 C8 C9 O14 0.3(16) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C7 C8 C9 C10 179.5(14) . . . . ?
O14 C9 C10 C11 179.3(12) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C10 C11 C12 Cl15 178.7(10) . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
Cl15 C12 C13 C8 -178.7(10) . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C7 C8 C13 C12 -179.6(13) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.094

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

data_6
_database_code_depnum_ccdc_archive 'CCDC 1451200'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 Br N4 O'
_chemical_formula_sum            'C9 H7 Br N4 O'
_chemical_formula_weight         267.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.4933(16)
_cell_length_b                   10.4263(13)
_cell_length_c                   7.2548(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.731(13)
_cell_angle_gamma                90
_cell_volume                     1018.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2159
_cell_measurement_theta_min      3.5750
_cell_measurement_theta_max      25.3900

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    4.013
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87865
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '90 images, ΔΦ 2.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2757
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.026
_diffrn_reflns_theta_max         25.227
_diffrn_reflns_theta_full        25.227
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2757
_reflns_number_gt                2216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;






_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+3.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2757
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0075(4) 0.3026(5) 0.3299(9) 0.0412(14) Uani 1 1 d . . . . .
N2 N -0.0187(4) 0.4004(6) 0.2046(8) 0.0383(14) Uani 1 1 d . . . . .
C3 C 0.0431(5) 0.4941(7) 0.2400(10) 0.0374(16) Uani 1 1 d . . . . .
H3 H 0.0419 0.5733 0.1751 0.045 Uiso 1 1 calc R U . . .
N4 N 0.1098(4) 0.4638(5) 0.3826(8) 0.0329(12) Uani 1 1 d . . . . .
C5 C 0.0848(5) 0.3422(7) 0.4301(10) 0.0392(16) Uani 1 1 d . . . . .
H5 H 0.1193 0.2930 0.5240 0.047 Uiso 1 1 calc R U . . .
N6 N 0.1919(4) 0.5305(5) 0.4630(8) 0.0342(13) Uani 1 1 d . . . . .
C7 C 0.1887(5) 0.6531(7) 0.4468(9) 0.0332(14) Uani 1 1 d . . . . .
H7 H 0.1318 0.6921 0.3862 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2705(4) 0.7340(7) 0.5192(9) 0.0339(15) Uani 1 1 d . . . . .
C9 C 0.3607(5) 0.6838(7) 0.5943(9) 0.0355(15) Uani 1 1 d . . . . .
C10 C 0.4357(5) 0.7669(9) 0.6573(10) 0.0425(19) Uani 1 1 d . . . . .
H10 H 0.4968 0.7332 0.7086 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4224(5) 0.8987(8) 0.6461(10) 0.0422(18) Uani 1 1 d . . . . .
H11 H 0.4741 0.9549 0.6901 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3330(5) 0.9481(7) 0.5702(10) 0.0388(16) Uani 1 1 d . . . . .
C13 C 0.2579(4) 0.8669(6) 0.5046(9) 0.0346(15) Uani 1 1 d . . . . .
H13 H 0.1978 0.9012 0.4497 0.042 Uiso 1 1 calc R U . . .
O14 O 0.3786(4) 0.5555(5) 0.6101(7) 0.0450(13) Uani 1 1 d . . . . .
H14 H 0.3284 0.5147 0.5684 0.067 Uiso 1 1 calc R U . . .
Br15 Br 0.31378(6) 1.12893(7) 0.55592(15) 0.0613(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.299(9) . ?
N1 N2 1.396(8) . ?
N2 C3 1.299(9) . ?
C3 N4 1.364(8) . ?
C3 H3 0.9500 . ?
N4 C5 1.362(9) . ?
N4 N6 1.403(7) . ?
C5 H5 0.9500 . ?
N6 C7 1.285(9) . ?
C7 C8 1.459(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(9) . ?
C8 C13 1.399(10) . ?
C9 O14 1.362(9) . ?
C9 C10 1.387(10) . ?
C10 C11 1.387(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(9) . ?
C12 Br15 1.905(7) . ?
C13 H13 0.9500 . ?
O14 H14 0.8400 . ?

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
C5 N1 N2 107.0(6) . . ?
C3 N2 N1 106.7(5) . . ?
N2 C3 N4 111.0(6) . . ?
N2 C3 H3 124.5 . . ?
N4 C3 H3 124.5 . . ?
C5 N4 C3 104.2(6) . . ?
C5 N4 N6 123.9(5) . . ?
C3 N4 N6 131.7(5) . . ?
N1 C5 N4 110.9(6) . . ?
N1 C5 H5 124.5 . . ?
N4 C5 H5 124.5 . . ?
C7 N6 N4 115.7(5) . . ?
N6 C7 C8 121.5(6) . . ?
N6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C13 119.8(6) . . ?
C9 C8 C7 122.8(6) . . ?
C13 C8 C7 117.4(6) . . ?
O14 C9 C10 117.7(6) . . ?
O14 C9 C8 122.9(6) . . ?
C10 C9 C8 119.4(7) . . ?
C9 C10 C11 120.8(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.6(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 Br15 119.6(5) . . ?
C11 C12 Br15 119.9(5) . . ?
C12 C13 C8 119.9(6) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C9 O14 H14 109.5 . . ?

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 N2 C3 -1.4(8) . . . . ?
N1 N2 C3 N4 0.2(8) . . . . ?
N2 C3 N4 C5 1.0(8) . . . . ?
N2 C3 N4 N6 176.6(6) . . . . ?
N2 N1 C5 N4 2.1(8) . . . . ?
C3 N4 C5 N1 -1.9(8) . . . . ?
N6 N4 C5 N1 -178.0(6) . . . . ?
C5 N4 N6 C7 -159.4(6) . . . . ?
C3 N4 N6 C7 25.7(10) . . . . ?
N4 N6 C7 C8 -178.2(6) . . . . ?
N6 C7 C8 C9 6.3(11) . . . . ?
N6 C7 C8 C13 -176.4(6) . . . . ?
C13 C8 C9 O14 -179.0(6) . . . . ?
C7 C8 C9 O14 -1.7(10) . . . . ?
C13 C8 C9 C10 1.5(10) . . . . ?
C7 C8 C9 C10 178.8(6) . . . . ?
O14 C9 C10 C11 -179.8(6) . . . . ?
C8 C9 C10 C11 -0.2(11) . . . . ?
C9 C10 C11 C12 -0.3(11) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C10 C11 C12 Br15 179.6(5) . . . . ?
C11 C12 C13 C8 1.9(10) . . . . ?
Br15 C12 C13 C8 -178.3(5) . . . . ?
C9 C8 C13 C12 -2.3(10) . . . . ?
C7 C8 C13 C12 -179.7(6) . . . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.100

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

data_7
_database_code_depnum_ccdc_archive 'CCDC 1451201'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_7                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A data cut-off to 0.95A was imposed beyond which the data
quality in terms of of I/sigma and Rint.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N4 O2'
_chemical_formula_sum            'C9 H8 N4 O2'
_chemical_formula_weight         204.19

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

_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   11.7895(5)
_cell_length_b                   11.7895(5)
_cell_length_c                   17.6053(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2119.2(2)
_cell_formula_units_Z            9
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3630
_cell_measurement_theta_min      1.9906
_cell_measurement_theta_max      21.9392

_exptl_crystal_description       needle
_exptl_crystal_colour            orange-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             954
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '133 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3464
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         21.986
_diffrn_reflns_theta_full        21.986
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3464
_reflns_number_gt                2777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;




_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.3582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1134 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3464
_refine_ls_number_parameters     407
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5765(9) 0.6293(10) 0.0550(6) 0.064(3) Uani 1 1 d . . . . .
N2 N 0.6337(10) 0.6515(9) -0.0185(5) 0.064(3) Uani 1 1 d . . . . .
C3 C 0.7433(12) 0.6543(12) -0.0084(6) 0.069(3) Uani 1 1 d . . . . .
H3 H 0.8028 0.6697 -0.0472 0.083 Uiso 1 1 calc R U . . .
N4 N 0.7631(8) 0.6320(8) 0.0657(5) 0.053(3) Uani 1 1 d . . . . .
C5 C 0.6586(12) 0.6213(11) 0.1032(7) 0.058(3) Uani 1 1 d . . . . .
H5 H 0.6459 0.6100 0.1554 0.069 Uiso 1 1 calc R U . . .
N6 N 0.8668(8) 0.6266(8) 0.1035(5) 0.053(2) Uani 1 1 d . . . . .
C7 C 0.9526(11) 0.6173(10) 0.0603(6) 0.051(3) Uani 1 1 d . . . . .
H7 H 0.9413 0.6112 0.0078 0.061 Uiso 1 1 calc R U . . .
C8 C 1.0637(10) 0.6164(10) 0.0930(6) 0.046(3) Uani 1 1 d . . . . .
C9 C 1.0841(12) 0.6227(13) 0.1686(6) 0.072(4) Uani 1 1 d . . . . .
C10 C 1.1994(12) 0.6272(13) 0.1959(6) 0.075(4) Uani 1 1 d . . . . .
H10 H 1.2191 0.6378 0.2475 0.090 Uiso 1 1 calc R U . . .
C11 C 1.2821(13) 0.6155(11) 0.1451(7) 0.065(3) Uani 1 1 d . . . . .
H11 H 1.3546 0.6122 0.1630 0.078 Uiso 1 1 calc R U . . .
C12 C 1.2586(11) 0.6086(10) 0.0669(6) 0.057(3) Uani 1 1 d . . . . .
C13 C 1.1479(11) 0.6075(10) 0.0418(6) 0.053(3) Uani 1 1 d . . . . .
H13 H 1.1293 0.6007 -0.0098 0.064 Uiso 1 1 calc R U . . .
O14 O 1.0082(9) 0.6338(10) 0.2229(4) 0.101(4) Uani 1 1 d . . . . .
H14 H 0.9467 0.6361 0.2026 0.152 Uiso 1 1 calc R U . . .
O15 O 1.3415(8) 0.5996(8) 0.0142(5) 0.077(3) Uani 1 1 d . . . . .
H15 H 1.4035 0.6013 0.0364 0.116 Uiso 1 1 calc R U . . .
N21 N -0.1060(10) 0.2794(11) 0.0399(6) 0.070(3) Uani 1 1 d . . . . .
N22 N -0.0577(11) 0.2816(12) -0.0329(6) 0.080(3) Uani 1 1 d . . . . .
C23 C 0.0492(13) 0.2807(13) -0.0246(6) 0.076(4) Uani 1 1 d . . . . .
H23 H 0.1002 0.2799 -0.0646 0.091 Uiso 1 1 calc R U . . .
N24 N 0.0804(8) 0.2811(8) 0.0515(4) 0.046(2) Uani 1 1 d . . . . .
C25 C -0.0195(12) 0.2805(11) 0.0868(6) 0.058(3) Uani 1 1 d . . . . .
H25 H -0.0271 0.2809 0.1394 0.070 Uiso 1 1 calc R U . . .
N26 N 0.1887(9) 0.2852(8) 0.0868(5) 0.048(2) Uani 1 1 d . . . . .
C27 C 0.2756(11) 0.2845(10) 0.0449(6) 0.049(3) Uani 1 1 d . . . . .
H27 H 0.2650 0.2805 -0.0076 0.059 Uiso 1 1 calc R U . . .
C28 C 0.3893(10) 0.2896(10) 0.0764(5) 0.047(3) Uani 1 1 d . . . . .
C29 C 0.4197(12) 0.3050(11) 0.1526(6) 0.058(3) Uani 1 1 d . . . . .
C30 C 0.5350(11) 0.3115(11) 0.1783(6) 0.065(3) Uani 1 1 d . . . . .
H30 H 0.5547 0.3225 0.2299 0.078 Uiso 1 1 calc R U . . .
C31 C 0.6221(11) 0.3016(13) 0.1275(7) 0.070(4) Uani 1 1 d . . . . .
H31 H 0.6984 0.3056 0.1451 0.084 Uiso 1 1 calc R U . . .
C32 C 0.5916(10) 0.2856(12) 0.0507(6) 0.062(3) Uani 1 1 d . . . . .
C33 C 0.4785(10) 0.2822(10) 0.0260(6) 0.054(3) Uani 1 1 d . . . . .
H33 H 0.4606 0.2748 -0.0258 0.065 Uiso 1 1 calc R U . . .
O34 O 0.3398(9) 0.3140(9) 0.2050(4) 0.085(3) Uani 1 1 d . . . . .
H34 H 0.2756 0.3088 0.1836 0.128 Uiso 1 1 calc R U . . .
O35 O 0.6733(8) 0.2787(10) -0.0014(4) 0.096(3) Uani 1 1 d . . . . .
H35 H 0.7361 0.2817 0.0205 0.144 Uiso 1 1 calc R U . . .
N41 N 0.0419(9) 0.7398(8) 0.4493(5) 0.050(2) Uani 1 1 d . . . . .
N42 N 0.0505(11) 0.6967(9) 0.5218(5) 0.069(3) Uani 1 1 d . . . . .
C43 C 0.0520(15) 0.5886(11) 0.5131(6) 0.074(4) Uani 1 1 d . . . . .
H43 H 0.0558 0.5382 0.5526 0.089 Uiso 1 1 calc R U . . .
N44 N 0.0474(9) 0.5592(7) 0.4391(4) 0.044(2) Uani 1 1 d . . . . .
C45 C 0.0426(12) 0.6562(11) 0.4022(6) 0.054(3) Uani 1 1 d . . . . .
H45 H 0.0401 0.6625 0.3496 0.065 Uiso 1 1 calc R U . . .
N46 N 0.0461(9) 0.4539(8) 0.4026(4) 0.044(2) Uani 1 1 d . . . . .
C47 C 0.0507(10) 0.3691(9) 0.4438(6) 0.040(2) Uani 1 1 d . . . . .
H47 H 0.0567 0.3809 0.4962 0.048 Uiso 1 1 calc R U . . .
C48 C 0.0467(9) 0.2521(9) 0.4118(5) 0.039(2) Uani 1 1 d . . . . .
C49 C 0.0385(11) 0.2269(9) 0.3323(5) 0.048(3) Uani 1 1 d . . . . .
C50 C 0.0348(11) 0.1137(10) 0.3074(6) 0.054(3) Uani 1 1 d . . . . .
H50 H 0.0288 0.0970 0.2555 0.065 Uiso 1 1 calc R U . . .
C51 C 0.0393(11) 0.0282(10) 0.3544(6) 0.052(3) Uani 1 1 d . . . . .
H51 H 0.0353 -0.0473 0.3354 0.062 Uiso 1 1 calc R U . . .
C52 C 0.0501(10) 0.0520(9) 0.4323(6) 0.046(3) Uani 1 1 d . . . . .
C53 C 0.0512(9) 0.1603(8) 0.4601(5) 0.041(2) Uani 1 1 d . . . . .
H53 H 0.0550 0.1735 0.5123 0.049 Uiso 1 1 calc R U . . .
O54 O 0.0340(10) 0.3111(8) 0.2807(4) 0.083(3) Uani 1 1 d . . . . .
H54 H 0.0370 0.3735 0.3031 0.125 Uiso 1 1 calc R U . . .
O55 O 0.0578(8) -0.0300(8) 0.4843(4) 0.072(2) Uani 1 1 d . . . . .
H55 H 0.0564 -0.0919 0.4621 0.108 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.325(15) . ?
N1 N2 1.422(13) . ?
N2 C3 1.289(14) . ?
C3 N4 1.373(13) . ?
C3 H3 0.9300 . ?
N4 C5 1.347(13) . ?
N4 N6 1.422(13) . ?
C5 H5 0.9300 . ?
N6 C7 1.313(12) . ?
C7 C8 1.435(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.349(15) . ?
C8 C13 1.383(15) . ?
C9 O14 1.359(13) . ?
C9 C10 1.418(16) . ?
C10 C11 1.380(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(15) . ?
C12 O15 1.389(13) . ?
C13 H13 0.9300 . ?
O14 H14 0.8200 . ?
O15 H15 0.8200 . ?
N21 C25 1.306(14) . ?
N21 N22 1.399(13) . ?
N22 C23 1.274(13) . ?
C23 N24 1.387(13) . ?
C23 H23 0.9300 . ?
N24 C25 1.329(13) . ?
N24 N26 1.399(11) . ?
C25 H25 0.9300 . ?
N26 C27 1.266(12) . ?
C27 C28 1.424(14) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(13) . ?
C28 C33 1.412(13) . ?
C29 O34 1.360(13) . ?
C29 C30 1.398(15) . ?
C30 C31 1.409(16) . ?
C30 H30 0.9300 . ?
C31 C32 1.388(16) . ?
C31 H31 0.9300 . ?
C32 O35 1.361(13) . ?
C32 C33 1.383(14) . ?
C33 H33 0.9300 . ?
O34 H34 0.8200 . ?
O35 H35 0.8200 . ?
N41 C45 1.292(12) . ?
N41 N42 1.396(12) . ?
N42 C43 1.292(13) . ?
C43 N44 1.343(13) . ?
C43 H43 0.9300 . ?
N44 C45 1.342(12) . ?
N44 N46 1.391(10) . ?
C45 H45 0.9300 . ?
N46 C47 1.258(12) . ?
C47 C48 1.469(13) . ?
C47 H47 0.9300 . ?
C48 C53 1.398(12) . ?
C48 C49 1.423(12) . ?
C49 O54 1.366(11) . ?
C49 C50 1.383(13) . ?
C50 C51 1.326(14) . ?
C50 H50 0.9300 . ?
C51 C52 1.394(14) . ?
C51 H51 0.9300 . ?
C52 C53 1.361(13) . ?
C52 O55 1.366(11) . ?
C53 H53 0.9300 . ?
O54 H54 0.8200 . ?
O55 H55 0.8200 . ?

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
C5 N1 N2 107.4(9) . . ?
C3 N2 N1 104.8(9) . . ?
N2 C3 N4 113.0(10) . . ?
N2 C3 H3 123.5 . . ?
N4 C3 H3 123.5 . . ?
C5 N4 C3 104.4(10) . . ?
C5 N4 N6 122.2(10) . . ?
C3 N4 N6 133.3(10) . . ?
N1 C5 N4 110.2(11) . . ?
N1 C5 H5 124.9 . . ?
N4 C5 H5 124.9 . . ?
C7 N6 N4 116.7(9) . . ?
N6 C7 C8 120.8(10) . . ?
N6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C13 122.2(11) . . ?
C9 C8 C7 122.3(11) . . ?
C13 C8 C7 115.5(10) . . ?
C8 C9 O14 126.2(11) . . ?
C8 C9 C10 118.5(11) . . ?
O14 C9 C10 115.1(10) . . ?
C11 C10 C9 119.2(11) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.0(12) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 O15 119.2(9) . . ?
C13 C12 C11 118.5(11) . . ?
O15 C12 C11 122.3(11) . . ?
C12 C13 C8 120.4(10) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C9 O14 H14 109.5 . . ?
C12 O15 H15 109.5 . . ?
C25 N21 N22 105.7(9) . . ?
C23 N22 N21 106.8(9) . . ?
N22 C23 N24 111.9(9) . . ?
N22 C23 H23 124.0 . . ?
N24 C23 H23 124.0 . . ?
C25 N24 C23 102.6(9) . . ?
C25 N24 N26 125.7(9) . . ?
C23 N24 N26 131.7(9) . . ?
N21 C25 N24 112.9(10) . . ?
N21 C25 H25 123.5 . . ?
N24 C25 H25 123.5 . . ?
C27 N26 N24 117.9(9) . . ?
N26 C27 C28 121.3(9) . . ?
N26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C29 C28 C33 117.8(10) . . ?
C29 C28 C27 124.3(10) . . ?
C33 C28 C27 117.8(9) . . ?
O34 C29 C28 121.7(11) . . ?
O34 C29 C30 117.9(9) . . ?
C28 C29 C30 120.3(11) . . ?
C29 C30 C31 121.2(10) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 118.7(11) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
O35 C32 C33 119.2(10) . . ?
O35 C32 C31 121.4(10) . . ?
C33 C32 C31 119.4(11) . . ?
C32 C33 C28 122.5(10) . . ?
C32 C33 H33 118.7 . . ?
C28 C33 H33 118.7 . . ?
C29 O34 H34 109.5 . . ?
C32 O35 H35 109.5 . . ?
C45 N41 N42 106.3(7) . . ?
C43 N42 N41 106.8(9) . . ?
N42 C43 N44 110.6(10) . . ?
N42 C43 H43 124.7 . . ?
N44 C43 H43 124.7 . . ?
C45 N44 C43 105.3(8) . . ?
C45 N44 N46 123.4(8) . . ?
C43 N44 N46 131.3(8) . . ?
N41 C45 N44 111.0(8) . . ?
N41 C45 H45 124.5 . . ?
N44 C45 H45 124.5 . . ?
C47 N46 N44 117.2(8) . . ?
N46 C47 C48 122.0(9) . . ?
N46 C47 H47 119.0 . . ?
C48 C47 H47 119.0 . . ?
C53 C48 C49 117.4(8) . . ?
C53 C48 C47 119.8(8) . . ?
C49 C48 C47 122.7(9) . . ?
O54 C49 C50 119.7(9) . . ?
O54 C49 C48 121.6(8) . . ?
C50 C49 C48 118.7(9) . . ?
C51 C50 C49 122.8(10) . . ?
C51 C50 H50 118.6 . . ?
C49 C50 H50 118.6 . . ?
C50 C51 C52 119.7(10) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C53 C52 O55 116.8(9) . . ?
C53 C52 C51 119.9(9) . . ?
O55 C52 C51 123.2(9) . . ?
C52 C53 C48 121.5(9) . . ?
C52 C53 H53 119.3 . . ?
C48 C53 H53 119.3 . . ?
C49 O54 H54 109.5 . . ?
C52 O55 H55 109.5 . . ?

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 N2 C3 0.3(12) . . . . ?
N1 N2 C3 N4 1.7(13) . . . . ?
N2 C3 N4 C5 -3.1(13) . . . . ?
N2 C3 N4 N6 -179.5(9) . . . . ?
N2 N1 C5 N4 -2.2(12) . . . . ?
C3 N4 C5 N1 3.2(12) . . . . ?
N6 N4 C5 N1 -179.9(8) . . . . ?
C5 N4 N6 C7 169.6(10) . . . . ?
C3 N4 N6 C7 -14.5(16) . . . . ?
N4 N6 C7 C8 177.5(9) . . . . ?
N6 C7 C8 C9 1.1(17) . . . . ?
N6 C7 C8 C13 -179.4(10) . . . . ?
C13 C8 C9 O14 178.8(12) . . . . ?
C7 C8 C9 O14 -2(2) . . . . ?
C13 C8 C9 C10 3.3(19) . . . . ?
C7 C8 C9 C10 -177.2(11) . . . . ?
C8 C9 C10 C11 -4.6(19) . . . . ?
O14 C9 C10 C11 179.4(12) . . . . ?
C9 C10 C11 C12 4.5(19) . . . . ?
C10 C11 C12 C13 -3.0(17) . . . . ?
C10 C11 C12 O15 178.6(11) . . . . ?
O15 C12 C13 C8 -179.9(9) . . . . ?
C11 C12 C13 C8 1.6(16) . . . . ?
C9 C8 C13 C12 -1.9(18) . . . . ?
C7 C8 C13 C12 178.6(9) . . . . ?
C25 N21 N22 C23 1.5(15) . . . . ?
N21 N22 C23 N24 -1.4(16) . . . . ?
N22 C23 N24 C25 0.8(14) . . . . ?
N22 C23 N24 N26 -177.4(10) . . . . ?
N22 N21 C25 N24 -1.1(14) . . . . ?
C23 N24 C25 N21 0.2(13) . . . . ?
N26 N24 C25 N21 178.5(9) . . . . ?
C25 N24 N26 C27 179.6(10) . . . . ?
C23 N24 N26 C27 -2.6(16) . . . . ?
N24 N26 C27 C28 179.4(9) . . . . ?
N26 C27 C28 C29 -4.8(17) . . . . ?
N26 C27 C28 C33 177.1(9) . . . . ?
C33 C28 C29 O34 179.5(10) . . . . ?
C27 C28 C29 O34 1.4(18) . . . . ?
C33 C28 C29 C30 -0.7(16) . . . . ?
C27 C28 C29 C30 -178.8(10) . . . . ?
O34 C29 C30 C31 179.4(11) . . . . ?
C28 C29 C30 C31 -0.5(17) . . . . ?
C29 C30 C31 C32 0.2(17) . . . . ?
C30 C31 C32 O35 178.3(11) . . . . ?
C30 C31 C32 C33 1.1(17) . . . . ?
O35 C32 C33 C28 -179.7(9) . . . . ?
C31 C32 C33 C28 -2.4(17) . . . . ?
C29 C28 C33 C32 2.2(16) . . . . ?
C27 C28 C33 C32 -179.6(10) . . . . ?
C45 N41 N42 C43 -1.7(14) . . . . ?
N41 N42 C43 N44 1.1(15) . . . . ?
N42 C43 N44 C45 -0.1(15) . . . . ?
N42 C43 N44 N46 -179.6(10) . . . . ?
N42 N41 C45 N44 1.7(13) . . . . ?
C43 N44 C45 N41 -1.0(14) . . . . ?
N46 N44 C45 N41 178.4(9) . . . . ?
C45 N44 N46 C47 -179.8(11) . . . . ?
C43 N44 N46 C47 -0.5(16) . . . . ?
N44 N46 C47 C48 178.5(9) . . . . ?
N46 C47 C48 C53 -179.6(9) . . . . ?
N46 C47 C48 C49 0.5(16) . . . . ?
C53 C48 C49 O54 -179.9(10) . . . . ?
C47 C48 C49 O54 0.1(16) . . . . ?
C53 C48 C49 C50 0.3(14) . . . . ?
C47 C48 C49 C50 -179.7(10) . . . . ?
O54 C49 C50 C51 179.7(11) . . . . ?
C48 C49 C50 C51 -0.4(17) . . . . ?
C49 C50 C51 C52 -0.9(17) . . . . ?
C50 C51 C52 C53 2.4(16) . . . . ?
C50 C51 C52 O55 -178.7(10) . . . . ?
O55 C52 C53 C48 178.5(9) . . . . ?
C51 C52 C53 C48 -2.5(15) . . . . ?
C49 C48 C53 C52 1.1(14) . . . . ?
C47 C48 C53 C52 -178.8(9) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.033

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

data_8
_database_code_depnum_ccdc_archive 'CCDC 1451202'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N4 O'
_chemical_formula_sum            'C13 H10 N4 O'
_chemical_formula_weight         238.25

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7625(6)
_cell_length_b                   5.8854(4)
_cell_length_c                   11.0081(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.833(7)
_cell_angle_gamma                90
_cell_volume                     567.41(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2106
_cell_measurement_theta_min      2.3208
_cell_measurement_theta_max      25.6689

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.75502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.5°'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4774
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.325
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2045
_reflns_number_gt                1725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.942

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

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?





_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0895P)²+0.0685P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 631 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6779(4) -0.1009(7) 0.5312(4) 0.0638(9) Uani 1 1 d . . . . .
N2 N 0.8370(3) -0.0743(6) 0.5244(3) 0.0574(8) Uani 1 1 d . . . . .
C3 C 0.8596(4) 0.1014(7) 0.4569(4) 0.0539(9) Uani 1 1 d . . . . .
H3 H 0.9554 0.1562 0.4376 0.065 Uiso 1 1 calc R U . . .
N4 N 0.7251(3) 0.1960(6) 0.4176(3) 0.0489(7) Uani 1 1 d . . . . .
C5 C 0.6172(4) 0.0624(7) 0.4653(4) 0.0617(11) Uani 1 1 d . . . . .
H5 H 0.5127 0.0839 0.4528 0.074 Uiso 1 1 calc R U . . .
N6 N 0.6893(3) 0.3792(6) 0.3416(3) 0.0539(8) Uani 1 1 d . . . . .
C7 C 0.7998(4) 0.5064(6) 0.3082(3) 0.0505(9) Uani 1 1 d . . . . .
H7 H 0.8987 0.4737 0.3361 0.061 Uiso 1 1 calc R U . . .
C8 C 0.7741(4) 0.6987(7) 0.2285(4) 0.0522(9) Uani 1 1 d . . . . .
C9 C 0.6281(5) 0.7525(8) 0.1820(4) 0.0605(11) Uani 1 1 d . . . . .
C10 C 0.6020(5) 0.9442(9) 0.1080(4) 0.0710(13) Uani 1 1 d . . . . .
H10 H 0.5043 0.9740 0.0763 0.085 Uiso 1 1 calc R U . . .
C11 C 0.7189(5) 1.0857(8) 0.0827(4) 0.0664(11) Uani 1 1 d . . . . .
H11 H 0.6998 1.2119 0.0336 0.080 Uiso 1 1 calc R U . . .
C12 C 0.8695(5) 1.0464(7) 0.1289(4) 0.0581(10) Uani 1 1 d . . . . .
C13 C 0.8994(4) 0.8463(6) 0.1984(4) 0.0520(9) Uani 1 1 d . . . . .
O14 O 0.5025(3) 0.6266(6) 0.2066(3) 0.0780(10) Uani 1 1 d . . . . .
H14 H 0.5260 0.5269 0.2558 0.117 Uiso 1 1 calc R U . . .
C15 C 1.0538(5) 0.8068(8) 0.2389(4) 0.0618(11) Uani 1 1 d . . . . .
H15 H 1.0778 0.6751 0.2821 0.074 Uiso 1 1 calc R U . . .
C16 C 1.1670(5) 0.9598(8) 0.2153(4) 0.0704(13) Uani 1 1 d . . . . .
H16 H 1.2665 0.9303 0.2426 0.084 Uiso 1 1 calc R U . . .
C17 C 1.1349(6) 1.1603(9) 0.1503(5) 0.0752(13) Uani 1 1 d . . . . .
H17 H 1.2119 1.2655 0.1373 0.090 Uiso 1 1 calc R U . . .
C18 C 0.9899(6) 1.1998(8) 0.1064(4) 0.0674(12) Uani 1 1 d . . . . .
H18 H 0.9697 1.3300 0.0608 0.081 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.308(6) . ?
N1 N2 1.407(4) . ?
N2 C3 1.293(5) . ?
C3 N4 1.361(5) . ?
C3 H3 0.9300 . ?
N4 C5 1.349(5) . ?
N4 N6 1.394(4) . ?
C5 H5 0.9300 . ?
N6 C7 1.287(5) . ?
C7 C8 1.446(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(5) . ?
C8 C13 1.447(5) . ?
C9 O14 1.361(5) . ?
C9 C10 1.406(6) . ?
C10 C11 1.356(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(6) . ?
C11 H11 0.9300 . ?
C12 C18 1.416(6) . ?
C12 C13 1.424(5) . ?
C13 C15 1.430(6) . ?
O14 H14 0.8200 . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.403(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
C5 N1 N2 105.9(3) . . ?
C3 N2 N1 106.9(3) . . ?
N2 C3 N4 111.3(3) . . ?
N2 C3 H3 124.4 . . ?
N4 C3 H3 124.4 . . ?
C5 N4 C3 104.4(3) . . ?
C5 N4 N6 122.5(3) . . ?
C3 N4 N6 133.1(3) . . ?
N1 C5 N4 111.5(3) . . ?
N1 C5 H5 124.2 . . ?
N4 C5 H5 124.2 . . ?
C7 N6 N4 117.6(3) . . ?
N6 C7 C8 121.6(3) . . ?
N6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 C13 118.2(4) . . ?
C7 C8 C13 120.3(3) . . ?
O14 C9 C8 122.7(4) . . ?
O14 C9 C10 115.7(4) . . ?
C8 C9 C10 121.6(4) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.7(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C18 C12 C11 121.5(4) . . ?
C18 C12 C13 119.7(4) . . ?
C11 C12 C13 118.8(4) . . ?
C12 C13 C15 117.3(4) . . ?
C12 C13 C8 119.5(3) . . ?
C15 C13 C8 123.2(4) . . ?
C9 O14 H14 109.5 . . ?
C16 C15 C13 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C13 C15 H15 119.4 . . ?
C15 C16 C17 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.5(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C12 121.3(5) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?

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 N2 C3 0.6(4) . . . . ?
N1 N2 C3 N4 0.1(4) . . . . ?
N2 C3 N4 C5 -0.7(5) . . . . ?
N2 C3 N4 N6 -177.8(3) . . . . ?
N2 N1 C5 N4 -1.0(5) . . . . ?
C3 N4 C5 N1 1.1(5) . . . . ?
N6 N4 C5 N1 178.6(3) . . . . ?
C5 N4 N6 C7 174.9(4) . . . . ?
C3 N4 N6 C7 -8.5(6) . . . . ?
N4 N6 C7 C8 179.3(3) . . . . ?
N6 C7 C8 C9 -1.3(6) . . . . ?
N6 C7 C8 C13 176.3(3) . . . . ?
C7 C8 C9 O14 -1.2(6) . . . . ?
C13 C8 C9 O14 -178.9(4) . . . . ?
C7 C8 C9 C10 177.7(4) . . . . ?
C13 C8 C9 C10 0.0(6) . . . . ?
O14 C9 C10 C11 177.2(4) . . . . ?
C8 C9 C10 C11 -1.8(7) . . . . ?
C9 C10 C11 C12 0.1(7) . . . . ?
C10 C11 C12 C18 -177.3(4) . . . . ?
C10 C11 C12 C13 3.4(7) . . . . ?
C18 C12 C13 C15 -2.1(5) . . . . ?
C11 C12 C13 C15 177.2(4) . . . . ?
C18 C12 C13 C8 175.6(4) . . . . ?
C11 C12 C13 C8 -5.1(6) . . . . ?
C9 C8 C13 C12 3.5(5) . . . . ?
C7 C8 C13 C12 -174.2(3) . . . . ?
C9 C8 C13 C15 -179.0(4) . . . . ?
C7 C8 C13 C15 3.3(5) . . . . ?
C12 C13 C15 C16 2.2(6) . . . . ?
C8 C13 C15 C16 -175.4(4) . . . . ?
C13 C15 C16 C17 0.0(7) . . . . ?
C15 C16 C17 C18 -2.3(7) . . . . ?
C16 C17 C18 C12 2.4(7) . . . . ?
C11 C12 C18 C17 -179.5(5) . . . . ?
C13 C12 C18 C17 -0.2(7) . . . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.041

