# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mo_NITK405_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1432094'
_audit_update_record             
;
2015-10-19 deposited with the CCDC.
2016-01-22 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         ?
_chemical_formula_sum            'C13 H16 N4 O3'
_chemical_formula_weight         276.30

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

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

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

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

_cell_length_a                   7.683(2)
_cell_length_b                   8.2572(19)
_cell_length_c                   11.518(3)
_cell_angle_alpha                92.271(15)
_cell_angle_beta                 96.041(16)
_cell_angle_gamma                102.027(15)
_cell_volume                     709.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  apexIIduo
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5635
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.740
_diffrn_measured_fraction_theta_full 0.755
_diffrn_reflns_Laue_measured_fraction_max 0.740
_diffrn_reflns_Laue_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_point_group_measured_fraction_full 0.755
_reflns_number_total             2062
_reflns_number_gt                1440
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.9100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2062
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.2137
_refine_ls_wR_factor_gt          0.1779
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9110(4) 0.8843(3) 0.39032(19) 0.0616(9) Uani 1 1 d . . . . .
O3 O 0.4495(4) 0.7253(4) 0.1004(2) 0.0647(9) Uani 1 1 d . . . . .
N2 N 0.8341(5) 0.7169(4) 0.5416(2) 0.0612(10) Uani 1 1 d . . . . .
O2 O 0.3770(5) 0.6237(5) 0.2692(3) 0.0847(11) Uani 1 1 d . . . . .
N1 N 0.9838(5) 1.0468(5) 0.2472(3) 0.0615(11) Uani 1 1 d . . . . .
N3 N 0.7646(5) 0.5529(5) 0.5450(3) 0.0627(11) Uani 1 1 d . . . . .
C6 C 0.9179(5) 0.8923(5) 0.2719(3) 0.0507(10) Uani 1 1 d . . . . .
C4 C 0.7812(5) 0.5794(4) 0.2277(3) 0.0480(10) Uani 1 1 d . . . . .
C5 C 0.8561(5) 0.7545(4) 0.1962(3) 0.0463(10) Uani 1 1 d . . . . .
N4 N 0.8768(5) 0.8024(5) -0.0216(3) 0.0710(11) Uani 1 1 d . . . . .
C3 C 0.8443(5) 0.7334(5) 0.4279(3) 0.0514(10) Uani 1 1 d . . . . .
C00C C 0.7811(5) 0.5867(5) 0.3595(3) 0.0513(11) Uani 1 1 d . . . . .
C7 C 0.8684(5) 0.7826(5) 0.0758(3) 0.0511(10) Uani 1 1 d . . . . .
C9 C 0.4602(6) 0.6230(5) 0.1860(3) 0.0573(11) Uani 1 1 d . . . . .
C8 C 0.5857(6) 0.5119(5) 0.1661(3) 0.0567(11) Uani 1 1 d . . . . .
C2 C 0.7317(6) 0.4697(5) 0.4388(3) 0.0566(11) Uani 1 1 d . . . . .
C00H C 0.8952(7) 0.4615(6) 0.1882(4) 0.0655(13) Uani 1 1 d . . . . .
C1 C 0.6543(7) 0.2892(5) 0.4276(4) 0.0755(14) Uani 1 1 d . . . . .
H1A H 0.5368 0.2692 0.3849 0.113 Uiso 1 1 calc R U . . .
H1B H 0.6462 0.2480 0.5041 0.113 Uiso 1 1 calc R U . . .
H1C H 0.7296 0.2335 0.3866 0.113 Uiso 1 1 calc R U . . .
C10 C 0.3419(8) 0.8490(7) 0.1158(5) 0.0761(15) Uani 1 1 d . . . . .
C11 C 0.4481(8) 0.9950(7) 0.1874(6) 0.110(2) Uani 1 1 d . . . . .
H11A H 0.4737 0.9649 0.2661 0.165 Uiso 1 1 calc R U . . .
H11B H 0.3814 1.0812 0.1877 0.165 Uiso 1 1 calc R U . . .
H11C H 0.5584 1.0340 0.1552 0.165 Uiso 1 1 calc R U . . .
H2 H 1.007(6) 1.071(5) 0.179(4) 0.056(12) Uiso 1 1 d . . . . .
H1 H 1.041(7) 1.127(6) 0.310(5) 0.105(17) Uiso 1 1 d . . . . .
H3 H 0.732(6) 0.508(6) 0.610(4) 0.065(12) Uiso 1 1 d . . . . .
H5 H 0.606(5) 0.509(4) 0.085(4) 0.058(11) Uiso 1 1 d . . . . .
H4 H 0.544(6) 0.393(6) 0.197(4) 0.076(13) Uiso 1 1 d . . . . .
H7 H 1.016(6) 0.489(5) 0.227(4) 0.074(13) Uiso 1 1 d . . . . .
H8 H 0.904(5) 0.469(4) 0.101(4) 0.053(10) Uiso 1 1 d . . . . .
H6 H 0.843(6) 0.333(7) 0.207(4) 0.094(16) Uiso 1 1 d . . . . .
H9 H 0.328(7) 0.887(7) 0.034(5) 0.110(18) Uiso 1 1 d . . . . .
H10 H 0.241(9) 0.785(8) 0.162(6) 0.13(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.351(5) . ?
O1 C6 1.374(4) . ?
O3 C9 1.330(5) . ?
O3 C10 1.458(6) . ?
N2 C3 1.332(5) . ?
N2 N3 1.352(5) . ?
O2 C9 1.207(5) . ?
N1 C6 1.325(5) . ?
N1 H2 0.85(5) . ?
N1 H1 0.97(5) . ?
N3 C2 1.352(5) . ?
N3 H3 0.88(5) . ?
C6 C5 1.375(5) . ?
C4 C5 1.514(5) . ?
C4 C00C 1.517(5) . ?
C4 C00H 1.526(6) . ?
C4 C8 1.571(5) . ?
C5 C7 1.424(5) . ?
N4 C7 1.147(5) . ?
C3 C00C 1.386(5) . ?
C00C C2 1.379(5) . ?
C9 C8 1.491(6) . ?
C8 H5 0.97(4) . ?
C8 H4 1.06(5) . ?
C2 C1 1.480(6) . ?
C00H H7 0.97(4) . ?
C00H H8 1.01(4) . ?
C00H H6 1.10(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 C11 1.473(7) . ?
C10 H9 1.01(6) . ?
C10 H10 1.04(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C3 O1 C6 116.3(3) . . ?
C9 O3 C10 116.6(4) . . ?
C3 N2 N3 102.4(3) . . ?
C6 N1 H2 122(3) . . ?
C6 N1 H1 119(3) . . ?
H2 N1 H1 117(5) . . ?
N2 N3 C2 113.8(4) . . ?
N2 N3 H3 122(3) . . ?
C2 N3 H3 124(3) . . ?
N1 C6 O1 110.0(3) . . ?
N1 C6 C5 128.5(3) . . ?
O1 C6 C5 121.5(4) . . ?
C5 C4 C00C 106.4(3) . . ?
C5 C4 C00H 110.6(4) . . ?
C00C C4 C00H 111.3(3) . . ?
C5 C4 C8 111.6(3) . . ?
C00C C4 C8 110.1(3) . . ?
C00H C4 C8 106.9(3) . . ?
C6 C5 C7 115.1(4) . . ?
C6 C5 C4 127.0(3) . . ?
C7 C5 C4 117.9(3) . . ?
N2 C3 O1 119.4(3) . . ?
N2 C3 C00C 113.7(4) . . ?
O1 C3 C00C 126.9(3) . . ?
C2 C00C C3 104.3(3) . . ?
C2 C00C C4 133.9(3) . . ?
C3 C00C C4 121.8(4) . . ?
N4 C7 C5 178.8(4) . . ?
O2 C9 O3 122.6(4) . . ?
O2 C9 C8 125.4(4) . . ?
O3 C9 C8 112.0(4) . . ?
C9 C8 C4 113.8(3) . . ?
C9 C8 H5 110(2) . . ?
C4 C8 H5 101(2) . . ?
C9 C8 H4 113(2) . . ?
C4 C8 H4 106(2) . . ?
H5 C8 H4 113(3) . . ?
N3 C2 C00C 105.8(3) . . ?
N3 C2 C1 120.4(4) . . ?
C00C C2 C1 133.8(3) . . ?
C4 C00H H7 112(2) . . ?
C4 C00H H8 109(2) . . ?
H7 C00H H8 107(4) . . ?
C4 C00H H6 113(3) . . ?
H7 C00H H6 105(3) . . ?
H8 C00H H6 110(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C10 C11 110.5(4) . . ?
O3 C10 H9 101(3) . . ?
C11 C10 H9 105(3) . . ?
O3 C10 H10 102(3) . . ?
C11 C10 H10 110(3) . . ?
H9 C10 H10 127(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_mo_NITK409_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1432095'
_audit_update_record             
;
2015-10-19 deposited with the CCDC.
2016-01-22 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         ?
_chemical_formula_sum            'C17 H14 Cl N5 O2'
_chemical_formula_weight         355.78

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

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

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

_cell_length_a                   8.4863(4)
_cell_length_b                   10.0369(5)
_cell_length_c                   10.8206(5)
_cell_angle_alpha                87.988(3)
_cell_angle_beta                 78.876(3)
_cell_angle_gamma                66.293(3)
_cell_volume                     827.10(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  apexIIduo
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10903
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.920
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.918
_reflns_number_total             2964
_reflns_number_gt                2102
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.9791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2722
_refine_ls_wR_factor_gt          0.2616
_refine_ls_goodness_of_fit_ref   1.458
_refine_ls_restrained_S_all      1.458
_refine_ls_shift/su_max          0.007
_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
Cl1 Cl 0.9791(3) 0.6589(2) 0.34269(18) 0.0807(8) Uani 1 1 d . . . . .
O2 O 0.2758(5) 0.8640(4) 0.9297(4) 0.0364(9) Uani 1 1 d . . . . .
O1 O 0.8287(5) 0.6159(4) 0.9733(4) 0.0407(10) Uani 1 1 d . . . . .
N2 N 0.7822(5) 0.4065(4) 0.9503(4) 0.0345(11) Uani 1 1 d . . . . .
N1 N 0.6796(6) 0.3740(5) 0.8852(4) 0.0340(11) Uani 1 1 d . . . . .
N5 N 0.3210(5) 0.8746(5) 0.7149(4) 0.0352(11) Uani 1 1 d . . . . .
N3 N 0.8651(7) 0.8176(6) 1.0003(5) 0.0473(14) Uani 1 1 d . . . . .
C10 C 0.5758(6) 0.7524(5) 0.7995(4) 0.0251(11) Uani 1 1 d . . . . .
C9 C 0.3725(6) 0.8370(5) 0.8272(5) 0.0273(11) Uani 1 1 d . . . . .
C14 C 0.7477(6) 0.5432(5) 0.9237(5) 0.0290(11) Uani 1 1 d . . . . .
C11 C 0.6660(6) 0.8251(5) 0.8665(5) 0.0273(11) Uani 1 1 d . . . . .
C15 C 0.6290(6) 0.6005(5) 0.8448(4) 0.0255(11) Uani 1 1 d . . . . .
C3 C 0.4650(7) 0.8284(5) 0.6130(5) 0.0315(12) Uani 1 1 d . . . . .
N4 N 0.6207(7) 1.0874(5) 0.8142(5) 0.0526(14) Uani 1 1 d . . . . .
C13 C 0.7817(6) 0.7578(5) 0.9435(5) 0.0303(12) Uani 1 1 d . . . . .
C8 C 0.6185(6) 0.7575(5) 0.6574(5) 0.0281(11) Uani 1 1 d . . . . .
C16 C 0.5858(7) 0.4852(5) 0.8209(5) 0.0311(12) Uani 1 1 d . . . . .
C12 C 0.6391(7) 0.9705(6) 0.8383(5) 0.0318(12) Uani 1 1 d . . . . .
C4 C 0.4658(8) 0.8477(7) 0.4862(5) 0.0415(14) Uani 1 1 d . . . . .
C7 C 0.7781(8) 0.7041(6) 0.5761(5) 0.0366(13) Uani 1 1 d . . . . .
C6 C 0.7791(8) 0.7239(6) 0.4491(5) 0.0438(14) Uani 1 1 d . . . . .
C5 C 0.6260(9) 0.7955(6) 0.4042(6) 0.0469(16) Uani 1 1 d . . . . .
C17 C 0.4646(8) 0.4743(7) 0.7439(6) 0.0519(16) Uani 1 1 d . . . . .
H4 H 0.4758 0.3754 0.7400 0.078 Uiso 1 1 calc R U . . .
H6 H 0.4934 0.5039 0.6602 0.078 Uiso 1 1 calc R U . . .
H5 H 0.3462 0.5366 0.7815 0.078 Uiso 1 1 calc R U . . .
C2 C 0.1384(8) 0.9469(7) 0.7006(8) 0.0493(16) Uani 1 1 d . . . . .
C1 C 0.0719(9) 0.8437(9) 0.6542(8) 0.074(2) Uani 1 1 d . . . . .
H3 H 0.1433 0.7989 0.5744 0.111 Uiso 1 1 calc R U . . .
H2 H -0.0474 0.8965 0.6445 0.111 Uiso 1 1 calc R U . . .
H1 H 0.0772 0.7699 0.7141 0.111 Uiso 1 1 calc R U . . .
H7 H 0.666(9) 0.291(8) 0.903(7) 0.07(2) Uiso 1 1 d . . . . .
H8 H 0.958(8) 0.759(7) 1.029(5) 0.047(16) Uiso 1 1 d . . . . .
H9 H 0.839(8) 0.914(8) 0.993(6) 0.051(17) Uiso 1 1 d . . . . .
H11 H 0.072(9) 0.988(7) 0.782(7) 0.06(2) Uiso 1 1 d . . . . .
H10 H 0.126(8) 1.024(7) 0.645(6) 0.058(19) Uiso 1 1 d . . . . .
H13 H 0.631(7) 0.808(6) 0.320(6) 0.037(15) Uiso 1 1 d . . . . .
H12 H 0.358(7) 0.897(6) 0.454(5) 0.042(15) Uiso 1 1 d . . . . .
H14 H 0.880(7) 0.655(6) 0.603(5) 0.039(15) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.743(6) . ?
O2 C9 1.212(6) . ?
O1 C13 1.361(6) . ?
O1 C14 1.366(6) . ?
N2 C14 1.316(6) . ?
N2 N1 1.357(6) . ?
N1 C16 1.344(6) . ?
N1 H7 0.90(7) . ?
N5 C9 1.360(6) . ?
N5 C3 1.409(7) . ?
N5 C2 1.460(7) . ?
N3 C13 1.332(6) . ?
N3 H8 0.88(6) . ?
N3 H9 0.91(7) . ?
C10 C15 1.499(6) . ?
C10 C8 1.514(7) . ?
C10 C11 1.531(6) . ?
C10 C9 1.558(7) . ?
C14 C15 1.381(6) . ?
C11 C13 1.363(6) . ?
C11 C12 1.416(7) . ?
C15 C16 1.393(6) . ?
C3 C4 1.378(8) . ?
C3 C8 1.381(7) . ?
N4 C12 1.146(6) . ?
C8 C7 1.373(7) . ?
C16 C17 1.480(7) . ?
C4 C5 1.380(9) . ?
C4 H12 0.98(6) . ?
C7 C6 1.381(8) . ?
C7 H14 0.91(6) . ?
C6 C5 1.381(9) . ?
C5 H13 0.91(6) . ?
C17 H4 0.9600 . ?
C17 H6 0.9600 . ?
C17 H5 0.9600 . ?
C2 C1 1.503(9) . ?
C2 H11 0.96(7) . ?
C2 H10 0.95(7) . ?
C1 H3 0.9600 . ?
C1 H2 0.9600 . ?
C1 H1 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
C13 O1 C14 115.6(4) . . ?
C14 N2 N1 102.1(4) . . ?
C16 N1 N2 113.9(4) . . ?
C16 N1 H7 128(5) . . ?
N2 N1 H7 117(4) . . ?
C9 N5 C3 111.7(4) . . ?
C9 N5 C2 124.4(5) . . ?
C3 N5 C2 123.8(5) . . ?
C13 N3 H8 118(4) . . ?
C13 N3 H9 119(4) . . ?
H8 N3 H9 122(5) . . ?
C15 C10 C8 113.2(4) . . ?
C15 C10 C11 106.2(4) . . ?
C8 C10 C11 112.7(4) . . ?
C15 C10 C9 111.4(4) . . ?
C8 C10 C9 101.4(4) . . ?
C11 C10 C9 112.1(4) . . ?
O2 C9 N5 125.5(5) . . ?
O2 C9 C10 126.7(4) . . ?
N5 C9 C10 107.8(4) . . ?
N2 C14 O1 119.6(4) . . ?
N2 C14 C15 114.9(4) . . ?
O1 C14 C15 125.5(4) . . ?
C13 C11 C12 116.9(4) . . ?
C13 C11 C10 125.3(4) . . ?
C12 C11 C10 117.6(4) . . ?
C14 C15 C16 103.4(4) . . ?
C14 C15 C10 123.5(4) . . ?
C16 C15 C10 133.0(4) . . ?
C4 C3 C8 121.5(5) . . ?
C4 C3 N5 128.8(5) . . ?
C8 C3 N5 109.7(4) . . ?
N3 C13 C11 126.4(5) . . ?
N3 C13 O1 109.9(4) . . ?
C11 C13 O1 123.7(4) . . ?
C7 C8 C3 120.9(5) . . ?
C7 C8 C10 129.7(4) . . ?
C3 C8 C10 109.4(4) . . ?
N1 C16 C15 105.7(4) . . ?
N1 C16 C17 123.1(4) . . ?
C15 C16 C17 131.2(5) . . ?
N4 C12 C11 178.7(6) . . ?
C3 C4 C5 117.8(5) . . ?
C3 C4 H12 122(3) . . ?
C5 C4 H12 120(3) . . ?
C8 C7 C6 117.6(5) . . ?
C8 C7 H14 122(3) . . ?
C6 C7 H14 120(3) . . ?
C7 C6 C5 121.7(6) . . ?
C7 C6 Cl1 119.1(5) . . ?
C5 C6 Cl1 119.1(5) . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H13 120(3) . . ?
C6 C5 H13 120(3) . . ?
C16 C17 H4 109.5 . . ?
C16 C17 H6 109.5 . . ?
H4 C17 H6 109.5 . . ?
C16 C17 H5 109.5 . . ?
H4 C17 H5 109.5 . . ?
H6 C17 H5 109.5 . . ?
N5 C2 C1 112.5(6) . . ?
N5 C2 H11 106(4) . . ?
C1 C2 H11 110(4) . . ?
N5 C2 H10 110(4) . . ?
C1 C2 H10 110(4) . . ?
H11 C2 H10 108(6) . . ?
C2 C1 H3 109.5 . . ?
C2 C1 H2 109.5 . . ?
H3 C1 H2 109.5 . . ?
C2 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H2 C1 H1 109.5 . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.059

