# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 1984299'
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl N O2'
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73

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'

_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                   7.0426(6)
_cell_length_b                   10.7671(10)
_cell_length_c                   18.0428(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.613(3)
_cell_angle_gamma                90
_cell_volume                     1352.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      28.38

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   
;
 Sheldrick, G.M. SADABS (Program for Scaling and Correction of Area Detector
 Data), version 2008/1; University of Göttingen: Göttingen, Germany, 2008.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19441
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.966
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3402
_reflns_number_gt                2841
_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 D8 Quest'
_computing_cell_refinement       'Bruker D8 Quest'
_computing_data_reduction        'Bruker D8 Quest'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0766P)²+1.5009P] 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         3402
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_restrained_S_all      0.816
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.22505(18) 0.13457(11) 0.52653(8) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.2060(2) 0.13047(14) 0.60274(9) 0.0226(3) Uani 1 1 d . . . . .
C6 C 0.0054(2) 0.31030(14) 0.50130(9) 0.0240(3) Uani 1 1 d . . . . .
H6A H -0.013036 0.392591 0.476797 0.029 Uiso 1 1 calc R U . . .
H6B H -0.103119 0.256425 0.479974 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0858(2) 0.22521(15) 0.70856(9) 0.0252(3) Uani 1 1 d . . . . .
H7A H 0.017122 0.289629 0.728857 0.030 Uiso 1 1 calc R U . . .
C8 C 0.1045(2) 0.22568(14) 0.63246(9) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.1674(2) 0.13109(16) 0.75361(9) 0.0280(3) Uani 1 1 d . . . . .
C10 C 0.1831(2) 0.21055(15) 0.40508(9) 0.0248(3) Uani 1 1 d . . . . .
C11 C 0.1931(2) 0.25361(14) 0.48509(9) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.2863(2) 0.03486(15) 0.64976(10) 0.0291(3) Uani 1 1 d . . . . .
H12A H 0.353976 -0.030803 0.630181 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2239(2) 0.08520(15) 0.40380(9) 0.0257(3) Uani 1 1 d . . . . .
C14 C 0.0053(2) 0.32477(14) 0.58424(9) 0.0257(3) Uani 1 1 d . . . . .
C15 C 0.2666(2) 0.03629(17) 0.72490(10) 0.0324(4) Uani 1 1 d . . . . .
H15A H 0.321687 -0.028368 0.756954 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2508(2) 0.03491(14) 0.48068(9) 0.0256(3) Uani 1 1 d . . . . .
C17 C 0.3634(2) 0.34090(16) 0.50747(10) 0.0306(4) Uani 1 1 d . . . . .
H17A H 0.340947 0.419160 0.479816 0.046 Uiso 1 1 calc R U . . .
H17B H 0.377540 0.357524 0.561421 0.046 Uiso 1 1 calc R U . . .
H17C H 0.480912 0.301946 0.495522 0.046 Uiso 1 1 calc R U . . .
C18 C 0.1391(3) 0.21427(19) 0.27216(10) 0.0351(4) Uani 1 1 d . . . . .
H18A H 0.106238 0.257543 0.226140 0.042 Uiso 1 1 calc R U . . .
C19 C 0.1400(2) 0.27782(17) 0.33959(9) 0.0300(3) Uani 1 1 d . . . . .
H19A H 0.112098 0.364088 0.340405 0.036 Uiso 1 1 calc R U . . .
C20 C 0.2278(2) 0.02258(16) 0.33679(10) 0.0317(4) Uani 1 1 d . . . . .
H20A H 0.258694 -0.063267 0.336251 0.038 Uiso 1 1 calc R U . . .
C21 C 0.1853(3) 0.08897(18) 0.27102(10) 0.0356(4) Uani 1 1 d . . . . .
H21A H 0.187631 0.048500 0.224377 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14056(7) 0.12928(5) 0.84766(2) 0.04195(16) Uani 1 1 d . . . . .
O2 O 0.28315(18) -0.07223(11) 0.50061(7) 0.0345(3) Uani 1 1 d . . . . .
O1 O -0.0762(2) 0.41026(12) 0.61023(7) 0.0395(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
N1 C16 1.383(2) . ?
N1 C5 1.402(2) . ?
N1 C11 1.4840(19) . ?
C5 C12 1.398(2) . ?
C5 C8 1.402(2) . ?
C6 C14 1.505(2) . ?
C6 C11 1.524(2) . ?
C7 C9 1.370(2) . ?
C7 C8 1.399(2) . ?
C8 C14 1.484(2) . ?
C9 C15 1.381(2) . ?
C9 Cl1 1.7355(17) . ?
C10 C13 1.381(2) . ?
C10 C19 1.380(2) . ?
C10 C11 1.508(2) . ?
C11 C17 1.530(2) . ?
C12 C15 1.383(2) . ?
C13 C20 1.388(2) . ?
C13 C16 1.475(2) . ?
C14 O1 1.215(2) . ?
C16 O2 1.220(2) . ?
C18 C21 1.389(3) . ?
C18 C19 1.395(2) . ?
C20 C21 1.379(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
C16 N1 C5 127.04(13) . . ?
C16 N1 C11 113.09(13) . . ?
C5 N1 C11 119.47(12) . . ?
C12 C5 C8 119.30(15) . . ?
C12 C5 N1 121.93(14) . . ?
C8 C5 N1 118.76(13) . . ?
C14 C6 C11 111.22(13) . . ?
C9 C7 C8 119.49(15) . . ?
C7 C8 C5 120.07(14) . . ?
C7 C8 C14 118.24(13) . . ?
C5 C8 C14 121.61(14) . . ?
C7 C9 C15 120.99(15) . . ?
C7 C9 Cl1 119.39(13) . . ?
C15 C9 Cl1 119.60(13) . . ?
C13 C10 C19 121.21(15) . . ?
C13 C10 C11 109.67(14) . . ?
C19 C10 C11 129.12(15) . . ?
N1 C11 C10 101.46(12) . . ?
N1 C11 C6 108.63(12) . . ?
C10 C11 C6 112.92(13) . . ?
N1 C11 C17 110.12(13) . . ?
C10 C11 C17 111.35(12) . . ?
C6 C11 C17 111.83(13) . . ?
C15 C12 C5 119.72(15) . . ?
C10 C13 C20 121.37(16) . . ?
C10 C13 C16 109.93(14) . . ?
C20 C13 C16 128.64(15) . . ?
O1 C14 C8 121.76(15) . . ?
O1 C14 C6 122.19(14) . . ?
C8 C14 C6 116.01(13) . . ?
C9 C15 C12 120.42(15) . . ?
O2 C16 N1 126.36(16) . . ?
O2 C16 C13 128.07(15) . . ?
N1 C16 C13 105.54(13) . . ?
C21 C18 C19 121.26(17) . . ?
C10 C19 C18 117.44(17) . . ?
C21 C20 C13 117.88(16) . . ?
C20 C21 C18 120.79(16) . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055

