# 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 2020

####################################################################### 
# 
# 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_141117a_0m
_database_code_depnum_ccdc_archive 'CCDC 1998453'
_audit_update_record             
;
2020-04-22 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 Cl N3 O2'
_chemical_formula_weight         323.73

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0960(7)
_cell_length_b                   7.6004(9)
_cell_length_c                   15.3686(18)
_cell_angle_alpha                85.0800(10)
_cell_angle_beta                 87.5620(10)
_cell_angle_gamma                78.9580(10)
_cell_volume                     696.05(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3596
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4982
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2436
_reflns_number_gt                2159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2436
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2255(3) 0.7317(2) 0.11550(11) 0.0444(4) Uani 1 1 d . . .
C2 C 0.0031(3) 0.6813(2) 0.08047(10) 0.0382(3) Uani 1 1 d . . .
C3 C 0.1692(3) 0.5883(2) 0.12991(10) 0.0414(4) Uani 1 1 d . . .
H3 H 0.3136 0.5613 0.1063 0.050 Uiso 1 1 calc R . .
C4 C 0.1244(3) 0.5305(2) 0.21929(10) 0.0393(4) Uani 1 1 d . . .
C5 C 0.2882(3) 0.4351(2) 0.27531(10) 0.0454(4) Uani 1 1 d . . .
H5 H 0.4360 0.4050 0.2557 0.054 Uiso 1 1 calc R . .
C6 C 0.2275(3) 0.3864(2) 0.36005(11) 0.0451(4) Uani 1 1 d . . .
C7 C 0.0074(3) 0.4254(2) 0.39020(11) 0.0472(4) Uani 1 1 d . . .
H7 H -0.0302 0.3880 0.4472 0.057 Uiso 1 1 calc R . .
C8 C -0.1545(3) 0.5189(2) 0.33594(11) 0.0481(4) Uani 1 1 d . . .
H8 H -0.3027 0.5459 0.3555 0.058 Uiso 1 1 calc R . .
C9 C -0.0941(3) 0.5725(2) 0.25149(10) 0.0402(4) Uani 1 1 d . . .
C10 C -0.0892(3) 0.8503(2) -0.06627(10) 0.0423(4) Uani 1 1 d . . .
H10 H -0.2313 0.9165 -0.0557 0.051 Uiso 1 1 calc R . .
C11 C 0.0324(3) 0.8489(2) -0.14252(10) 0.0386(3) Uani 1 1 d . . .
C12 C -0.0265(3) 0.9442(2) -0.22806(10) 0.0384(4) Uani 1 1 d . . .
C13 C 0.1361(3) 0.9576(2) -0.29290(11) 0.0478(4) Uani 1 1 d . . .
H13 H 0.2850 0.9084 -0.2819 0.057 Uiso 1 1 calc R . .
C14 C 0.0777(3) 1.0439(3) -0.37398(12) 0.0549(5) Uani 1 1 d . . .
H14 H 0.1878 1.0526 -0.4171 0.066 Uiso 1 1 calc R . .
C15 C -0.1414(3) 1.1167(2) -0.39117(11) 0.0531(4) Uani 1 1 d . . .
H15 H -0.1799 1.1736 -0.4459 0.064 Uiso 1 1 calc R . .
C16 C -0.3034(3) 1.1052(2) -0.32733(12) 0.0549(5) Uani 1 1 d . . .
H16 H -0.4518 1.1553 -0.3388 0.066 Uiso 1 1 calc R . .
C17 C -0.2477(3) 1.0197(2) -0.24618(11) 0.0496(4) Uani 1 1 d . . .
H17 H -0.3588 1.0127 -0.2034 0.060 Uiso 1 1 calc R . .
Cl1 Cl 0.42764(8) 0.27541(7) 0.43320(3) 0.0653(2) Uani 1 1 d . . .
N1 N 0.0407(2) 0.73499(17) -0.00907(8) 0.0386(3) Uani 1 1 d . . .
N2 N 0.2364(2) 0.6628(2) -0.04884(9) 0.0504(4) Uani 1 1 d . . .
N3 N 0.2306(2) 0.7322(2) -0.12945(9) 0.0499(4) Uani 1 1 d . . .
O1 O -0.26077(19) 0.67037(16) 0.20027(7) 0.0478(3) Uani 1 1 d . . .
O2 O -0.3820(2) 0.8205(2) 0.07803(8) 0.0647(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
C1 O2 1.196(2) . ?
C1 O1 1.368(2) . ?
C1 C2 1.465(2) . ?
C2 C3 1.342(2) . ?
C2 N1 1.423(2) . ?
C3 C4 1.437(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.389(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C6 Cl1 1.7388(17) . ?
C7 C8 1.369(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3723(19) . ?
C10 N1 1.353(2) . ?
C10 C11 1.359(2) . ?
C10 H10 0.9300 . ?
C11 N3 1.366(2) . ?
C11 C12 1.469(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 N2 1.3574(19) . ?
N2 N3 1.303(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 117.36(15) . . ?
O2 C1 C2 126.91(15) . . ?
O1 C1 C2 115.73(14) . . ?
C3 C2 N1 121.41(14) . . ?
C3 C2 C1 121.92(14) . . ?
N1 C2 C1 116.67(13) . . ?
C2 C3 C4 120.10(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C4 C5 118.45(14) . . ?
C9 C4 C3 117.92(14) . . ?
C5 C4 C3 123.63(15) . . ?
C6 C5 C4 119.02(16) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 121.60(16) . . ?
C5 C6 Cl1 120.57(14) . . ?
C7 C6 Cl1 117.83(13) . . ?
C8 C7 C6 119.88(15) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 118.88(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O1 C9 C8 116.85(14) . . ?
O1 C9 C4 121.03(14) . . ?
C8 C9 C4 122.12(15) . . ?
N1 C10 C11 105.27(14) . . ?
N1 C10 H10 127.4 . . ?
C11 C10 H10 127.4 . . ?
C10 C11 N3 108.09(14) . . ?
C10 C11 C12 129.68(15) . . ?
N3 C11 C12 122.19(14) . . ?
C13 C12 C17 118.62(15) . . ?
C13 C12 C11 120.87(14) . . ?
C17 C12 C11 120.50(14) . . ?
C14 C13 C12 120.31(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.45(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.73(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.49(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.40(16) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C10 N1 N2 110.18(13) . . ?
C10 N1 C2 131.13(13) . . ?
N2 N1 C2 118.69(12) . . ?
N3 N2 N1 107.05(13) . . ?
N2 N3 C11 109.41(13) . . ?
C1 O1 C9 123.22(13) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
