# 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_swj
_database_code_depnum_ccdc_archive 'CCDC 1865306'
_audit_update_record             
;
2018-09-01 deposited with the CCDC.
2019-01-07 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         'C19 H16 Cl N5 O'
_chemical_formula_sum            'C19 H16 Cl N5 O'
_chemical_formula_weight         365.82

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/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                   9.2973(4)
_cell_length_b                   16.7097(7)
_cell_length_c                   11.0503(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.760(4)
_cell_angle_gamma                90
_cell_volume                     1710.80(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    4229
_cell_measurement_theta_min      2.5180
_cell_measurement_theta_max      28.6440

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             760
_exptl_absorpt_correction_T_min  0.88158
_exptl_absorpt_correction_T_max  1.00000
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.803
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_reflns_number            11996
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3489
_reflns_number_gt                2886
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0412P)²+0.6788P] 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         3489
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.65960(18) -0.09013(10) 0.83622(17) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.76126(18) -0.02764(10) 0.85964(16) 0.0160(4) Uani 1 1 d . . . . .
C3 C 0.74844(18) -0.00855(10) 0.97972(16) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.86019(17) 0.00471(10) 0.77324(16) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.97516(18) 0.13232(11) 0.71615(16) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.97170(18) 0.21641(10) 0.73256(16) 0.0166(4) Uani 1 1 d . . . . .
C7 C 1.05895(18) 0.26360(11) 0.66442(17) 0.0201(4) Uani 1 1 d . . . . .
H7 H 1.0576 0.3188 0.6744 0.024 Uiso 1 1 calc R U . . .
C8 C 1.1472(2) 0.23111(11) 0.58276(17) 0.0230(4) Uani 1 1 d . . . . .
H8 H 1.2044 0.2639 0.5387 0.028 Uiso 1 1 calc R U . . .
C9 C 1.14905(19) 0.14883(11) 0.56748(17) 0.0229(4) Uani 1 1 d . . . . .
H9 H 1.2079 0.1263 0.5125 0.028 Uiso 1 1 calc R U . . .
C10 C 1.06439(19) 0.09990(11) 0.63310(18) 0.0225(4) Uani 1 1 d . . . . .
H10 H 1.0669 0.0448 0.6218 0.027 Uiso 1 1 calc R U . . .
C11 C 0.87825(18) 0.25457(10) 0.81689(15) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.71797(18) 0.27471(10) 0.94458(16) 0.0163(4) Uani 1 1 d . . . . .
C13 C 0.61131(19) 0.26693(11) 1.02545(17) 0.0205(4) Uani 1 1 d . . . . .
H13 H 0.5716 0.2173 1.0414 0.025 Uiso 1 1 calc R U . . .
C14 C 0.56680(19) 0.33560(11) 1.08095(17) 0.0215(4) Uani 1 1 d . . . . .
H14 H 0.4962 0.3321 1.1356 0.026 Uiso 1 1 calc R U . . .
C15 C 0.62581(19) 0.41040(11) 1.05665(17) 0.0220(4) Uani 1 1 d . . . . .
H15 H 0.5926 0.4555 1.0950 0.026 Uiso 1 1 calc R U . . .
C16 C 0.73231(19) 0.41899(11) 0.97701(18) 0.0220(4) Uani 1 1 d . . . . .
H16 H 0.7715 0.4687 0.9611 0.026 Uiso 1 1 calc R U . . .
C17 C 0.77763(18) 0.34961(11) 0.92208(16) 0.0174(4) Uani 1 1 d . . . . .
C18 C 0.6058(2) -0.06416(13) 1.14582(18) 0.0286(5) Uani 1 1 d . . . . .
H18A H 0.6737 -0.0980 1.1916 0.043 Uiso 1 1 calc R U . . .
H18B H 0.5113 -0.0874 1.1440 0.043 Uiso 1 1 calc R U . . .
H18C H 0.6049 -0.0123 1.1833 0.043 Uiso 1 1 calc R U . . .
C19 C 0.6201(2) -0.13489(11) 0.72096(18) 0.0237(4) Uani 1 1 d . . . . .
H19A H 0.5417 -0.1707 0.7326 0.036 Uiso 1 1 calc R U . . .
H19B H 0.7019 -0.1650 0.6991 0.036 Uiso 1 1 calc R U . . .
H19C H 0.5914 -0.0977 0.6573 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.83884(5) 0.05921(3) 1.07324(4) 0.02521(15) Uani 1 1 d . . . . .
N1 N 0.64762(16) -0.05612(9) 1.02248(14) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.59137(16) -0.10669(9) 0.93419(14) 0.0218(4) Uani 1 1 d . . . . .
N3 N 0.88749(15) 0.08393(8) 0.78413(14) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.8456 0.1081 0.8402 0.021 Uiso 1 1 calc R U . . .
N4 N 0.87992(15) 0.33526(8) 0.84061(13) 0.0176(3) Uani 1 1 d . . . . .
H4 H 0.9344 0.3703 0.8104 0.021 Uiso 1 1 calc R U . . .
N5 N 0.78186(15) 0.21640(9) 0.87694(14) 0.0183(3) Uani 1 1 d . . . . .
O1 O 0.90988(13) -0.04032(7) 0.69781(11) 0.0184(3) 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
C1 N2 1.329(2) . ?
C1 C2 1.418(2) . ?
C1 C19 1.496(3) . ?
C2 C3 1.380(2) . ?
C2 C4 1.482(2) . ?
C3 N1 1.344(2) . ?
C3 Cl1 1.7065(18) . ?
C4 O1 1.240(2) . ?
C4 N3 1.351(2) . ?
C5 C10 1.396(2) . ?
C5 N3 1.409(2) . ?
C5 C6 1.418(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.471(2) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N5 1.322(2) . ?
C11 N4 1.373(2) . ?
C12 N5 1.391(2) . ?
C12 C13 1.395(2) . ?
C12 C17 1.400(2) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 N4 1.384(2) . ?
C18 N1 1.454(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 N2 1.362(2) . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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
N2 C1 C2 111.15(16) . . ?
N2 C1 C19 119.31(16) . . ?
C2 C1 C19 129.52(16) . . ?
C3 C2 C1 103.67(15) . . ?
C3 C2 C4 130.04(16) . . ?
C1 C2 C4 126.24(16) . . ?
N1 C3 C2 108.65(16) . . ?
N1 C3 Cl1 120.15(14) . . ?
C2 C3 Cl1 131.18(14) . . ?
O1 C4 N3 125.20(15) . . ?
O1 C4 C2 119.84(15) . . ?
N3 C4 C2 114.96(15) . . ?
C10 C5 N3 121.97(16) . . ?
C10 C5 C6 119.31(16) . . ?
N3 C5 C6 118.72(15) . . ?
C7 C6 C5 118.07(16) . . ?
C7 C6 C11 119.82(16) . . ?
C5 C6 C11 122.11(15) . . ?
C8 C7 C6 122.29(17) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 118.96(17) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 120.65(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.72(17) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
N5 C11 N4 112.02(15) . . ?
N5 C11 C6 124.70(15) . . ?
N4 C11 C6 123.26(15) . . ?
N5 C12 C13 129.57(16) . . ?
N5 C12 C17 109.74(15) . . ?
C13 C12 C17 120.69(16) . . ?
C14 C13 C12 117.54(16) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C15 121.34(16) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 121.75(17) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 116.71(16) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 H16 121.6 . . ?
N4 C17 C16 132.71(16) . . ?
N4 C17 C12 105.34(15) . . ?
C16 C17 C12 121.95(16) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 C19 H19A 109.5 . . ?
C1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 N1 N2 110.65(15) . . ?
C3 N1 C18 129.23(17) . . ?
N2 N1 C18 119.84(15) . . ?
C1 N2 N1 105.88(14) . . ?
C4 N3 C5 128.87(15) . . ?
C4 N3 H3 115.6 . . ?
C5 N3 H3 115.6 . . ?
C11 N4 C17 107.27(14) . . ?
C11 N4 H4 126.4 . . ?
C17 N4 H4 126.4 . . ?
C11 N5 C12 105.62(14) . . ?

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
N2 C1 C2 C3 0.2(2) . . . . ?
C19 C1 C2 C3 178.44(18) . . . . ?
N2 C1 C2 C4 177.79(16) . . . . ?
C19 C1 C2 C4 -4.0(3) . . . . ?
C1 C2 C3 N1 0.03(19) . . . . ?
C4 C2 C3 N1 -177.39(16) . . . . ?
C1 C2 C3 Cl1 178.12(14) . . . . ?
C4 C2 C3 Cl1 0.7(3) . . . . ?
C3 C2 C4 O1 143.43(19) . . . . ?
C1 C2 C4 O1 -33.5(3) . . . . ?
C3 C2 C4 N3 -37.2(3) . . . . ?
C1 C2 C4 N3 145.93(17) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
N3 C5 C6 C7 -179.88(16) . . . . ?
C10 C5 C6 C11 178.88(16) . . . . ?
N3 C5 C6 C11 -0.8(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C11 C6 C7 C8 -179.08(17) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C5 0.0(3) . . . . ?
N3 C5 C10 C9 179.87(17) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C7 C6 C11 N5 173.32(17) . . . . ?
C5 C6 C11 N5 -5.7(3) . . . . ?
C7 C6 C11 N4 -5.5(3) . . . . ?
C5 C6 C11 N4 175.46(17) . . . . ?
N5 C12 C13 C14 -179.94(18) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 N4 -179.33(18) . . . . ?
C15 C16 C17 C12 0.7(3) . . . . ?
N5 C12 C17 N4 -0.66(19) . . . . ?
C13 C12 C17 N4 178.97(16) . . . . ?
N5 C12 C17 C16 179.31(17) . . . . ?
C13 C12 C17 C16 -1.1(3) . . . . ?
C2 C3 N1 N2 -0.3(2) . . . . ?
Cl1 C3 N1 N2 -178.62(12) . . . . ?
C2 C3 N1 C18 173.41(17) . . . . ?
Cl1 C3 N1 C18 -4.9(3) . . . . ?
C2 C1 N2 N1 -0.41(19) . . . . ?
C19 C1 N2 N1 -178.81(15) . . . . ?
C3 N1 N2 C1 0.43(19) . . . . ?
C18 N1 N2 C1 -173.94(16) . . . . ?
O1 C4 N3 C5 -0.3(3) . . . . ?
C2 C4 N3 C5 -179.60(16) . . . . ?
C10 C5 N3 C4 -8.5(3) . . . . ?
C6 C5 N3 C4 171.21(17) . . . . ?
N5 C11 N4 C17 0.3(2) . . . . ?
C6 C11 N4 C17 179.22(15) . . . . ?
C16 C17 N4 C11 -179.7(2) . . . . ?
C12 C17 N4 C11 0.25(19) . . . . ?
N4 C11 N5 C12 -0.7(2) . . . . ?
C6 C11 N5 C12 -179.60(16) . . . . ?
C13 C12 N5 C11 -178.78(18) . . . . ?
C17 C12 N5 C11 0.81(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
N4 H4 O1 0.86 2.09 2.9085(18) 159.7 2_756
N4 H4 Cl1 0.86 2.94 3.4347(16) 118.3 4_565
N3 H3 N5 0.86 1.96 2.661(2) 138.3 .
N3 H3 Cl1 0.86 2.71 3.2896(16) 126.3 .
C13 H13 N2 0.93 2.42 3.325(2) 164.6 3_657
C10 H10 O1 0.93 2.25 2.870(2) 123.5 .

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.057



