# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_1_32029301_0m
_database_code_depnum_ccdc_archive 'CCDC 1913605'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N5 O3.50'
_chemical_formula_weight         234.23

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.836(2)
_cell_length_b                   10.5330(8)
_cell_length_c                   7.2981(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.099(3)
_cell_angle_gamma                90
_cell_volume                     2159.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9402
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      28.29

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7228
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17786
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2672
_reflns_number_gt                2335
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0838P)²+2.2463P] 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         2672
_refine_ls_number_parameters     179
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.003
_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 0.32705(4) 0.83499(10) 0.18071(16) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.12015(4) 0.81148(12) 0.38745(17) 0.0166(3) Uani 1 1 d . . . . .
H1 H 0.3478(9) 0.764(3) 0.161(3) 0.046(7) Uiso 1 1 d . . . . .
O2 O 0.27633(4) 0.68012(10) 0.21008(16) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.07741(5) 0.79803(15) 0.4294(2) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.0675 0.7131 0.4422 0.021 Uiso 1 1 calc R U . . .
N3 N 0.04712(4) 0.88812(13) 0.45536(17) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.06414(5) 1.00559(14) 0.43676(19) 0.0137(3) Uani 1 1 d . . . . .
C5 C 0.10772(5) 1.03409(14) 0.39639(18) 0.0133(3) Uani 1 1 d . . . . .
N6 N 0.17926(4) 0.94679(12) 0.33013(17) 0.0141(3) Uani 1 1 d . . . . .
C6 C 0.13671(5) 0.93034(14) 0.37042(18) 0.0135(3) Uani 1 1 d . . . . .
H6 H 0.1895(7) 1.025(2) 0.323(3) 0.017(5) Uiso 1 1 d . . . . .
N7 N 0.11315(4) 1.16434(12) 0.38873(17) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.07343(5) 1.21117(15) 0.4239(2) 0.0165(3) Uani 1 1 d . . . . .
H8 H 0.0671 1.2995 0.4279 0.020 Uiso 1 1 calc R U . . .
N9 N 0.04276(4) 1.11965(12) 0.45359(17) 0.0152(3) Uani 1 1 d . . . . .
H9 H 0.0134(11) 1.131(3) 0.485(4) 0.056(8) Uiso 1 1 d . . . . .
C61 C 0.20865(5) 0.84201(14) 0.2923(2) 0.0144(3) Uani 1 1 d . . . . .
H61A H 0.1921 0.7960 0.1778 0.017 Uiso 1 1 calc R U . . .
H61B H 0.2145 0.7817 0.3991 0.017 Uiso 1 1 calc R U . . .
C62 C 0.25567(5) 0.89465(14) 0.2643(2) 0.0153(3) Uani 1 1 d . . . . .
H62A H 0.2493 0.9584 0.1620 0.018 Uiso 1 1 calc R U . . .
H62B H 0.2725 0.9379 0.3810 0.018 Uiso 1 1 calc R U . . .
C63 C 0.28707(5) 0.79191(14) 0.21588(19) 0.0141(3) Uani 1 1 d . . . . .
O1W O 0.12031(5) 0.56570(14) 0.2056(2) 0.0390(4) Uani 1 1 d . . . . .
H1W1 H 0.1317(10) 0.645(3) 0.292(4) 0.051 Uiso 1 1 d . U . . .
H1W2 H 0.1427(11) 0.502(3) 0.276(4) 0.051 Uiso 1 1 d . U . . .
O2W O 0.02936(11) 0.4630(4) 0.1526(8) 0.0754(14) Uani 0.5 1 d D . P . .
H2W1 H 0.021(2) 0.531(6) 0.054(9) 0.098 Uiso 0.5 1 d D U P . .
H2W2 H 0.0650(15) 0.476(7) 0.200(10) 0.098 Uiso 0.5 1 d D U P . .


_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 C63 1.3174(16) . ?
N1 C2 1.3431(17) . ?
N1 C6 1.3557(19) . ?
O2 C63 1.2158(18) . ?
C2 N3 1.3319(19) . ?
N3 C4 1.3493(19) . ?
C4 N9 1.3687(18) . ?
C4 C5 1.3870(18) . ?
C5 N7 1.383(2) . ?
C5 C6 1.4146(19) . ?
N6 C6 1.3360(17) . ?
N6 C61 1.4556(18) . ?
N7 C8 1.3244(18) . ?
C8 N9 1.3585(19) . ?
C61 C62 1.5208(19) . ?
C62 C63 1.5036(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 118.61(13) . . ?
N3 C2 N1 128.50(14) . . ?
C2 N3 C4 111.95(12) . . ?
N3 C4 N9 127.90(13) . . ?
N3 C4 C5 125.99(13) . . ?
N9 C4 C5 106.11(12) . . ?
N7 C5 C4 109.85(12) . . ?
N7 C5 C6 133.23(13) . . ?
C4 C5 C6 116.92(13) . . ?
C6 N6 C61 123.14(13) . . ?
N6 C6 N1 120.01(13) . . ?
N6 C6 C5 121.96(13) . . ?
N1 C6 C5 118.03(12) . . ?
C8 N7 C5 104.52(12) . . ?
N7 C8 N9 112.93(13) . . ?
C8 N9 C4 106.59(12) . . ?
N6 C61 C62 108.92(12) . . ?
C63 C62 C61 111.83(12) . . ?
O2 C63 O1 123.64(13) . . ?
O2 C63 C62 122.89(13) . . ?
O1 C63 C62 113.47(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N7 0.99(3) 1.64(3) 2.6185(17) 170(2) 4_545
N6 H6 O2 0.88(2) 1.95(2) 2.8173(17) 167.6(19) 4
C8 H8 O1W 0.95 2.66 3.212(2) 117.6 6_576
N9 H9 N3 0.93(3) 1.90(3) 2.8189(17) 167(3) 5_576
O1W H1W1 N1 1.05(3) 1.94(3) 2.910(2) 151(2) .
O1W H1W2 O1 0.99(3) 1.96(3) 2.8855(18) 155(2) 4_545
O2W H2W2 O1W 1.02(4) 1.85(6) 2.782(4) 151(6) .

_refine_diff_density_max         0.788
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_32035001_0m
_database_code_depnum_ccdc_archive 'CCDC 1913606'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H15 N5 O4'
_chemical_formula_weight         257.26

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/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                   11.9730(14)
_cell_length_b                   12.7692(14)
_cell_length_c                   14.8340(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.582(4)
_cell_angle_gamma                90
_cell_volume                     2257.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.31

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27614
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         28.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5616
_reflns_number_gt                3739
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0640P)²+2.2584P] 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         5616
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.017
_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
O1A O 0.84429(12) 0.09576(11) 0.03934(11) 0.0169(3) Uani 1 1 d . . . . .
H1A H 0.760(2) 0.1307(19) 0.0006(16) 0.020 Uiso 1 1 d . U . . .
N1A N 1.33287(16) -0.10065(13) 0.28739(13) 0.0167(4) Uani 1 1 d . . . . .
O2A O 0.88750(14) 0.26188(11) 0.07014(12) 0.0224(4) Uani 1 1 d . . . . .
C2A C 1.42029(19) -0.14151(17) 0.33515(16) 0.0198(5) Uani 1 1 d . . . . .
H2A H 1.475861 -0.094022 0.360431 0.024 Uiso 1 1 calc R U . . .
N3A N 1.43891(16) -0.24349(14) 0.35176(14) 0.0172(4) Uani 1 1 d . . . . .
H3A H 1.490(2) -0.256(2) 0.3813(19) 0.021 Uiso 1 1 d . U . . .
C4A C 1.35892(18) -0.30912(17) 0.31298(15) 0.0159(5) Uani 1 1 d . . . . .
C5A C 1.26391(18) -0.27392(16) 0.26159(15) 0.0161(5) Uani 1 1 d . . . . .
N6A N 1.15889(15) -0.12330(13) 0.20182(13) 0.0174(4) Uani 1 1 d . . . . .
H6A H 1.105317 -0.165164 0.178411 0.021 Uiso 1 1 calc R U . . .
C6A C 1.24846(18) -0.16466(17) 0.24903(16) 0.0176(5) Uani 1 1 d . . . . .
N7A N 1.20239(16) -0.35973(14) 0.23232(13) 0.0175(4) Uani 1 1 d . . . . .
H7A H 1.129(2) -0.3616(19) 0.1910(17) 0.021 Uiso 1 1 d . U . . .
C8A C 1.26138(19) -0.44169(17) 0.26642(15) 0.0188(5) Uani 1 1 d . . . . .
H8A H 1.237779 -0.512086 0.256182 0.023 Uiso 1 1 calc R U . . .
N9A N 1.35634(15) -0.41623(14) 0.31615(13) 0.0173(4) Uani 1 1 d . . . . .
C61A C 1.14702(18) -0.01089(16) 0.18783(16) 0.0175(5) Uani 1 1 d . . . . .
H61A H 1.206338 0.014427 0.151145 0.021 Uiso 1 1 calc R U . . .
H61B H 1.156173 0.025473 0.247027 0.021 Uiso 1 1 calc R U . . .
C62A C 1.03219(18) 0.01443(15) 0.13949(15) 0.0141(4) Uani 1 1 d . . . . .
H62A H 1.022019 -0.023695 0.081162 0.017 Uiso 1 1 calc R U . . .
H62B H 0.972864 -0.008728 0.177090 0.017 Uiso 1 1 calc R U . . .
C63A C 1.02164(18) 0.13155(15) 0.12230(16) 0.0162(5) Uani 1 1 d . . . . .
H63C H 1.033864 0.168234 0.181226 0.019 Uiso 1 1 calc R U . . .
H63D H 1.082432 0.153288 0.085605 0.019 Uiso 1 1 calc R U . . .
C64A C 0.91107(17) 0.16793(15) 0.07471(15) 0.0134(4) Uani 1 1 d . . . . .
O1B O 0.96368(14) -0.23574(11) 0.12192(13) 0.0274(4) Uani 1 1 d . . . . .
N1B N 0.53023(16) -0.59880(13) -0.11205(13) 0.0170(4) Uani 1 1 d . . . . .
O2B O 1.01994(13) -0.40097(11) 0.13240(11) 0.0202(4) Uani 1 1 d . . . . .
C2B C 0.43975(19) -0.64149(16) -0.15644(16) 0.0187(5) Uani 1 1 d . . . . .
H2B H 0.387852 -0.593668 -0.186370 0.022 Uiso 1 1 calc R U . . .
N3B N 0.41192(15) -0.74252(13) -0.16465(13) 0.0166(4) Uani 1 1 d . . . . .
C4B C 0.49242(18) -0.80473(16) -0.12238(15) 0.0150(4) Uani 1 1 d . . . . .
C5B C 0.59227(18) -0.77155(16) -0.07619(15) 0.0156(5) Uani 1 1 d . . . . .
N6B N 0.70272(16) -0.62030(13) -0.02504(13) 0.0169(4) Uani 1 1 d . . . . .
H6B H 0.754811 -0.662043 0.000902 0.020 Uiso 1 1 calc R U . . .
C6B C 0.61100(18) -0.66206(16) -0.06988(15) 0.0156(4) Uani 1 1 d . . . . .
N7B N 0.65439(15) -0.85671(14) -0.04383(13) 0.0174(4) Uani 1 1 d . . . . .
N9B N 0.49439(16) -0.91183(14) -0.11692(14) 0.0177(4) Uani 1 1 d . . . . .
H9B H 0.446(2) -0.953(2) -0.1412(18) 0.021 Uiso 1 1 d . U . . .
C61B C 0.71835(18) -0.50726(16) -0.01815(16) 0.0169(5) Uani 1 1 d . . . . .
H61C H 0.654753 -0.475458 0.009942 0.020 Uiso 1 1 calc R U . . .
H61D H 0.720112 -0.476945 -0.079423 0.020 Uiso 1 1 calc R U . . .
C62B C 0.82753(17) -0.48285(15) 0.03887(15) 0.0136(4) Uani 1 1 d . . . . .
H62C H 0.891244 -0.512636 0.009557 0.016 Uiso 1 1 calc R U . . .
H62D H 0.826798 -0.515563 0.099313 0.016 Uiso 1 1 calc R U . . .
C63B C 0.84288(18) -0.36524(15) 0.04949(15) 0.0150(4) Uani 1 1 d . . . . .
H63A H 0.841968 -0.333768 -0.011569 0.018 Uiso 1 1 calc R U . . .
H63B H 0.777823 -0.336689 0.077841 0.018 Uiso 1 1 calc R U . . .
C64B C 0.94930(18) -0.33085(15) 0.10528(15) 0.0144(4) Uani 1 1 d . . . . .
C8B C 0.59218(18) -0.93879(17) -0.07031(16) 0.0186(5) Uani 1 1 d . . . . .
H8B H 0.614188 -1.009182 -0.057751 0.022 Uiso 1 1 calc R U . . .
O1W O 0.64272(18) -1.19150(16) -0.07018(16) 0.0381(5) Uani 1 1 d . . . . .
H1W1 H 0.682(3) -1.212(3) -0.104(2) 0.046 Uiso 1 1 d . U . . .
H1W2 H 0.679(3) -1.171(3) -0.023(2) 0.046 Uiso 1 1 d . U . . .
O2W O 0.77723(15) -1.11353(13) 0.07578(13) 0.0245(4) Uani 1 1 d . . . . .
H2W1 H 0.833(2) -1.146(2) 0.091(2) 0.029 Uiso 1 1 d . U . . .
H2W2 H 0.804(2) -1.058(2) 0.066(2) 0.029 Uiso 1 1 d . U . . .
O3W O 0.2550(2) -0.7970(2) -0.30689(19) 0.0536(7) Uani 1 1 d . . . . .
H3W1 H 0.191(4) -0.817(3) -0.300(3) 0.064 Uiso 1 1 d . U . . .
H3W2 H 0.272(4) -0.772(3) -0.255(3) 0.079(15) Uiso 1 1 d . . . . .
O4W O 0.05044(14) -0.88823(13) -0.33641(13) 0.0240(4) Uani 1 1 d . . . . .
H4W1 H 0.036(2) -0.947(2) -0.3555(19) 0.029 Uiso 1 1 d . U . . .
H4W2 H -0.001(2) -0.851(2) -0.3660(19) 0.029 Uiso 1 1 d . 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
O1A C64A 1.297(2) . ?
N1A C2A 1.314(3) . ?
N1A C6A 1.379(3) . ?
O2A C64A 1.233(2) . ?
C2A N3A 1.340(3) . ?
N3A C4A 1.358(3) . ?
C4A N9A 1.369(3) . ?
C4A C5A 1.381(3) . ?
C5A N7A 1.367(3) . ?
C5A C6A 1.417(3) . ?
N6A C6A 1.332(3) . ?
N6A C61A 1.455(3) . ?
N7A C8A 1.334(3) . ?
C8A N9A 1.334(3) . ?
C61A C62A 1.522(3) . ?
C62A C63A 1.520(3) . ?
C63A C64A 1.512(3) . ?
O1B C64B 1.248(2) . ?
N1B C2B 1.329(3) . ?
N1B C6B 1.364(3) . ?
O2B C64B 1.270(2) . ?
C2B N3B 1.335(3) . ?
N3B C4B 1.355(3) . ?
C4B N9B 1.370(3) . ?
C4B C5B 1.385(3) . ?
C5B N7B 1.377(3) . ?
C5B C6B 1.418(3) . ?
N6B C6B 1.338(3) . ?
N6B C61B 1.458(3) . ?
N7B C8B 1.323(3) . ?
N9B C8B 1.345(3) . ?
C61B C62B 1.519(3) . ?
C62B C63B 1.519(3) . ?
C63B C64B 1.515(3) . ?

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
C2A N1A C6A 120.04(18) . . ?
N1A C2A N3A 126.5(2) . . ?
C2A N3A C4A 115.09(19) . . ?
N3A C4A N9A 128.3(2) . . ?
N3A C4A C5A 122.82(19) . . ?
N9A C4A C5A 108.90(19) . . ?
N7A C5A C4A 107.68(19) . . ?
N7A C5A C6A 133.4(2) . . ?
C4A C5A C6A 118.9(2) . . ?
C6A N6A C61A 121.91(19) . . ?
N6A C6A N1A 120.16(19) . . ?
N6A C6A C5A 123.2(2) . . ?
N1A C6A C5A 116.63(19) . . ?
C8A N7A C5A 105.03(18) . . ?
N9A C8A N7A 114.2(2) . . ?
C8A N9A C4A 104.21(18) . . ?
N6A C61A C62A 110.36(17) . . ?
C63A C62A C61A 110.15(17) . . ?
C64A C63A C62A 115.81(17) . . ?
O2A C64A O1A 122.72(19) . . ?
O2A C64A C63A 120.67(19) . . ?
O1A C64A C63A 116.62(17) . . ?
C2B N1B C6B 119.45(18) . . ?
N1B C2B N3B 128.8(2) . . ?
C2B N3B C4B 111.37(18) . . ?
N3B C4B N9B 128.3(2) . . ?
N3B C4B C5B 126.19(19) . . ?
N9B C4B C5B 105.49(19) . . ?
N7B C5B C4B 109.98(18) . . ?
N7B C5B C6B 132.8(2) . . ?
C4B C5B C6B 117.24(19) . . ?
C6B N6B C61B 121.53(18) . . ?
N6B C6B N1B 120.18(18) . . ?
N6B C6B C5B 122.9(2) . . ?
N1B C6B C5B 116.94(19) . . ?
C8B N7B C5B 104.63(18) . . ?
C8B N9B C4B 107.15(19) . . ?
N6B C61B C62B 109.87(17) . . ?
C61B C62B C63B 110.46(17) . . ?
C64B C63B C62B 115.46(17) . . ?
O1B C64B O2B 123.28(19) . . ?
O1B C64B C63B 118.85(18) . . ?
O2B C64B C63B 117.87(17) . . ?
N7B C8B N9B 112.74(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8B H8B O1W 0.95 2.36 3.283(3) 163.0 . yes
C2A H2A N1B 0.95 2.57 3.400(3) 146.2 4_656 yes
N3A H3A O1W 0.73(3) 2.01(3) 2.727(3) 164(3) 4_646 yes
N6A H6A O1B 0.88 2.03 2.897(2) 168.8 . yes
N7A H7A O1B 1.02(3) 2.68(3) 3.528(3) 141.0(18) . yes
N7A H7A O2B 1.02(3) 1.58(3) 2.572(2) 163(2) . yes
C8A H8A O3W 0.95 2.63 3.508(3) 154.5 4_646 yes
C2B H2B N1A 0.95 2.59 3.418(3) 146.3 4_455 yes
O3W H3W2 N3B 0.84(5) 2.08(5) 2.774(3) 140(4) . yes
N6B H6B O2A 0.88 2.05 2.923(2) 170.9 1_545 yes
N9B H9B N9A 0.84(3) 2.05(3) 2.867(3) 165(2) 4_445 yes
O1W H1W1 O3W 0.77(4) 1.92(4) 2.660(3) 162(4) 2_644 yes
O1W H1W2 O2W 0.83(4) 1.94(4) 2.756(3) 172(3) . yes
O3W H3W1 O4W 0.82(4) 1.94(4) 2.709(3) 155(4) . yes
O4W H4W1 O2B 0.81(3) 1.96(3) 2.750(2) 164(3) 4_445 yes
O4W H4W2 O2A 0.86(3) 1.93(3) 2.794(2) 178(3) 4_455 yes
O2W H2W1 O1B 0.80(3) 1.96(3) 2.755(2) 175(3) 1_545 yes
O2W H2W2 O1A 0.79(3) 2.07(3) 2.857(2) 170(3) 1_545 yes
O1A H1A N7B 1.19(2) 1.38(2) 2.552(2) 165(2) 1_565 yes

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.072


# start Validation Reply Form
_vrf_PLAT780_2_32035001_0m       
;
PROBLEM: Coordinates do not Form a Properly Connected Set     Please Do !  
RESPONSE: This alert is likely due to the short interactions O1-H-N, because no
symmetry operations are needed to get atoms in the bonding positions in the 
molecules.
;
####################################################################### 
# 
# 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_32040801_0m
_database_code_depnum_ccdc_archive 'CCDC 1913608'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 Cl N5 O2'
_chemical_formula_weight         257.69

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                   5.7390(3)
_cell_length_b                   9.8258(5)
_cell_length_c                   10.4109(5)
_cell_angle_alpha                72.819(2)
_cell_angle_beta                 85.079(2)
_cell_angle_gamma                85.218(2)
_cell_volume                     557.77(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      28.26

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    0.341
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7178
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24580
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2780
_reflns_number_gt                2499
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_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)+(0.0288P)²+0.3528P] 
 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         2780
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.21999(5) 0.37804(3) 0.16054(3) 0.01322(9) Uani 1 1 d . . . . .
O2 O -0.51177(17) -0.07357(11) 0.18340(10) 0.0201(2) Uani 1 1 d . . . . .
N3 N 0.38707(19) 0.45033(12) -0.32136(11) 0.0135(2) Uani 1 1 d . . . . .
N6 N -0.17089(19) 0.22168(12) -0.09857(11) 0.0124(2) Uani 1 1 d . . . . .
N1 N 0.16122(18) 0.35266(11) -0.11785(11) 0.0110(2) Uani 1 1 d . . . . .
O1 O -0.6329(2) -0.05326(13) 0.38621(10) 0.0272(3) Uani 1 1 d . . . . .
N7 N -0.04743(19) 0.24740(12) -0.39628(10) 0.0142(2) Uani 1 1 d . . . . .
N9 N 0.2479(2) 0.37919(12) -0.50611(11) 0.0142(2) Uani 1 1 d . . . . .
C8 C 0.0720(2) 0.29722(14) -0.51299(13) 0.0158(3) Uani 1 1 d . . . . .
H8 H 0.0385 0.2778 -0.5934 0.019 Uiso 1 1 calc R U . . .
C64 C -0.4910(2) -0.02501(14) 0.27644(13) 0.0144(3) Uani 1 1 d . . . . .
C5 C 0.0598(2) 0.30011(13) -0.30847(12) 0.0116(2) Uani 1 1 d . . . . .
C6 C 0.0078(2) 0.28800(13) -0.17041(12) 0.0106(2) Uani 1 1 d . . . . .
C61 C -0.2528(2) 0.22148(13) 0.03863(12) 0.0125(2) Uani 1 1 d . . . . .
H61A H -0.4246 0.2136 0.0491 0.015 Uiso 1 1 calc R U . . .
H61B H -0.2206 0.3139 0.0513 0.015 Uiso 1 1 calc R U . . .
C62 C -0.1398(2) 0.10108(13) 0.14886(12) 0.0134(2) Uani 1 1 d . . . . .
H62A H 0.0138 0.1289 0.1660 0.016 Uiso 1 1 calc R U . . .
H62B H -0.1131 0.0140 0.1189 0.016 Uiso 1 1 calc R U . . .
C63 C -0.2985(2) 0.06987(14) 0.27846(12) 0.0144(2) Uani 1 1 d . . . . .
H63A H -0.2030 0.0230 0.3561 0.017 Uiso 1 1 calc R U . . .
H63B H -0.3693 0.1610 0.2906 0.017 Uiso 1 1 calc R U . . .
C2 C 0.3370(2) 0.43062(13) -0.19251(13) 0.0128(2) Uani 1 1 d . . . . .
H2 H 0.4312 0.4744 -0.1472 0.015 Uiso 1 1 calc R U . . .
C4 C 0.2432(2) 0.38158(13) -0.37546(12) 0.0119(2) Uani 1 1 d . . . . .
H1 H -0.734(4) -0.116(3) 0.379(2) 0.055(7) Uiso 1 1 d . . . . .
H5 H -0.251(3) 0.1814(18) -0.1363(18) 0.019(4) Uiso 1 1 d . . . . .
H3 H 0.343(3) 0.422(2) -0.5693(19) 0.027(5) Uiso 1 1 d . . . . .
H4 H 0.147(3) 0.353(2) -0.033(2) 0.032(5) 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
O2 C64 1.2175(16) . ?
N3 C2 1.3074(16) . ?
N3 C4 1.3614(16) . ?
N6 C6 1.3144(16) . ?
N6 C61 1.4643(15) . ?
N1 C2 1.3605(15) . ?
N1 C6 1.3636(15) . ?
O1 C64 1.3181(16) . ?
N7 C8 1.3218(16) . ?
N7 C5 1.3830(16) . ?
N9 C8 1.3624(16) . ?
N9 C4 1.3652(16) . ?
C64 C63 1.5089(17) . ?
C5 C4 1.3851(16) . ?
C5 C6 1.4144(16) . ?
C61 C62 1.5279(18) . ?
C62 C63 1.5283(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 C4 112.26(10) . . ?
C6 N6 C61 126.54(11) . . ?
C2 N1 C6 123.56(11) . . ?
C8 N7 C5 104.09(10) . . ?
C8 N9 C4 106.58(10) . . ?
N7 C8 N9 113.10(11) . . ?
O2 C64 O1 122.73(12) . . ?
O2 C64 C63 123.42(11) . . ?
O1 C64 C63 113.83(11) . . ?
N7 C5 C4 110.36(11) . . ?
N7 C5 C6 131.25(11) . . ?
C4 C5 C6 118.35(11) . . ?
N6 C6 N1 122.63(11) . . ?
N6 C6 C5 123.89(11) . . ?
N1 C6 C5 113.48(10) . . ?
N6 C61 C62 114.18(10) . . ?
C61 C62 C63 110.14(10) . . ?
C64 C63 C62 112.08(10) . . ?
N3 C2 N1 125.49(11) . . ?
N3 C4 N9 127.43(11) . . ?
N3 C4 C5 126.69(11) . . ?
N9 C4 C5 105.88(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Cl1 0.95 2.62 3.3056(13) 129.9 1_554
C61 H61A Cl1 0.99 2.88 3.5849(13) 129.3 1_455
C62 H62A Cl1 0.99 2.79 3.5860(13) 137.8 .
C2 H2 Cl1 0.95 2.54 3.3797(12) 147.6 2_665
O1 H1 N7 0.90(2) 1.83(2) 2.7290(15) 170(2) 2_455
N6 H5 O2 0.821(18) 1.970(18) 2.7734(14) 165.7(17) 2_455
N9 H3 N3 0.847(19) 2.112(19) 2.9295(15) 162.2(18) 2_664
N1 H4 Cl1 0.88(2) 2.18(2) 3.0306(11) 162.3(17) .

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.055

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_32035002_0m
_database_code_depnum_ccdc_archive 'CCDC 1913607'
loop_
_audit_author_name
_audit_author_address
'Ezequiel Vazquez-Lopez'
;University of Vigo
Spain
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 Cl N5 O2'
_chemical_formula_weight         243.66

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           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                   4.4865(3)
_cell_length_b                   18.9802(13)
_cell_length_c                   11.8656(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.716(2)
_cell_angle_gamma                90
_cell_volume                     998.74(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.31

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.193
_exptl_absorpt_coefficient_mu    0.376
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14205
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.761
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2458
_reflns_number_gt                2311
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0320P)²+0.6499P] 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         2458
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
Cl1 Cl 0.05495(7) 0.19758(2) 0.17584(2) 0.01281(9) Uani 1 1 d . . . . .
O1 O 0.6488(2) 0.20630(5) 0.41620(8) 0.0160(2) Uani 1 1 d . . . . .
O2 O 0.5403(2) 0.10882(5) 0.31184(8) 0.0145(2) Uani 1 1 d . . . . .
N9 N 0.4755(2) 0.08818(6) 0.96961(9) 0.0111(2) Uani 1 1 d . . . . .
N3 N 0.7714(2) 0.00211(6) 0.88081(9) 0.0101(2) Uani 1 1 d . . . . .
N7 N 0.5563(2) 0.17879(6) 0.85711(9) 0.0111(2) Uani 1 1 d . . . . .
C63 C 0.6958(3) 0.14503(7) 0.39718(10) 0.0110(2) Uani 1 1 d . . . . .
N6 N 0.9326(2) 0.15710(6) 0.65677(9) 0.0107(2) Uani 1 1 d . . . . .
N1 N 1.0037(2) 0.04337(6) 0.72770(9) 0.0107(2) Uani 1 1 d . . . . .
C6 C 0.8820(3) 0.10932(6) 0.73344(10) 0.0097(2) Uani 1 1 d . . . . .
C62 C 0.9340(3) 0.10092(7) 0.46766(11) 0.0128(2) Uani 1 1 d . . . . .
H62A H 1.0754 0.0830 0.4180 0.015 Uiso 1 1 calc R U . . .
H62B H 0.8364 0.0598 0.4982 0.015 Uiso 1 1 calc R U . . .
C5 C 0.7087(3) 0.12205(6) 0.82131(10) 0.0095(2) Uani 1 1 d . . . . .
C8 C 0.4237(3) 0.15634(7) 0.94512(10) 0.0122(2) Uani 1 1 d . . . . .
H8 H 0.3056 0.1858 0.9856 0.015 Uiso 1 1 calc R U . . .
C2 C 0.9454(3) -0.00608(7) 0.79888(10) 0.0114(2) Uani 1 1 d . . . . .
H2 H 1.0331 -0.0511 0.7919 0.014 Uiso 1 1 calc R U . . .
C61 C 1.1112(3) 0.14145(7) 0.56646(10) 0.0124(2) Uani 1 1 d . . . . .
H61A H 1.2900 0.1135 0.5989 0.015 Uiso 1 1 calc R U . . .
H61B H 1.1837 0.1862 0.5374 0.015 Uiso 1 1 calc R U . . .
C4 C 0.6536(3) 0.06735(6) 0.89255(10) 0.0096(2) Uani 1 1 d . . . . .
H6 H 0.852(4) 0.1969(9) 0.6613(14) 0.011 Uiso 1 1 d . U . . .
H10 H 0.415(4) 0.1374(9) 0.2739(14) 0.011 Uiso 1 1 d . U . . .
H3 H 0.723(4) -0.0333(9) 0.9215(14) 0.011 Uiso 1 1 d . U . . .
H7 H 0.547(4) 0.2164(9) 0.8272(14) 0.011 Uiso 1 1 d . 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
O1 C63 1.2092(16) . ?
O2 C63 1.3305(15) . ?
N9 C8 1.3384(16) . ?
N9 C4 1.3610(16) . ?
N3 C2 1.3447(16) . ?
N3 C4 1.3618(16) . ?
N7 C8 1.3470(16) . ?
N7 C5 1.3767(15) . ?
C63 C62 1.5071(18) . ?
N6 C6 1.3282(16) . ?
N6 C61 1.4626(15) . ?
N1 C2 1.3153(16) . ?
N1 C6 1.3716(16) . ?
C6 C5 1.4126(16) . ?
C62 C61 1.5219(18) . ?
C5 C4 1.3845(16) . ?

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
C8 N9 C4 103.60(10) . . ?
C2 N3 C4 117.12(11) . . ?
C8 N7 C5 106.86(10) . . ?
O1 C63 O2 123.56(12) . . ?
O1 C63 C62 124.04(12) . . ?
O2 C63 C62 112.40(11) . . ?
C6 N6 C61 122.18(11) . . ?
C2 N1 C6 119.99(11) . . ?
N6 C6 N1 118.58(11) . . ?
N6 C6 C5 123.99(11) . . ?
N1 C6 C5 117.43(11) . . ?
C63 C62 C61 112.98(10) . . ?
N7 C5 C4 104.79(10) . . ?
N7 C5 C6 135.72(11) . . ?
C4 C5 C6 119.44(11) . . ?
N9 C8 N7 113.05(11) . . ?
N1 C2 N3 125.14(12) . . ?
N6 C61 C62 112.75(10) . . ?
N9 C4 N3 127.55(11) . . ?
N9 C4 C5 111.69(11) . . ?
N3 C4 C5 120.76(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C62 H62A O2 0.99 2.64 3.5166(16) 147.6 1_655
C8 H8 Cl1 0.95 2.68 3.4953(13) 144.4 1_556
C8 H8 O1 0.95 2.28 2.8824(16) 120.8 4_566
C2 H2 Cl1 0.95 2.84 3.6471(13) 143.2 3_656
N6 H6 Cl1 0.843(17) 2.426(18) 3.2626(12) 171.9(15) 4_666
O2 H10 Cl1 0.858(18) 2.168(18) 3.0199(11) 172.1(15) .
N3 H3 N9 0.874(17) 1.973(17) 2.8125(15) 160.4(15) 3_657
N7 H7 Cl1 0.795(18) 2.432(18) 3.1826(11) 157.9(15) 4_666

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

