# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_zj1227
_database_code_depnum_ccdc_archive 'CCDC 1973939'
loop_
_audit_author_name
_audit_author_address
'Huawen Huang'
;Xiangtan University
China
;
_audit_update_record             
;
2019-12-24 deposited with the CCDC.	2020-05-28 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            'C11 H8 Cl N O2'
_chemical_formula_weight         221.63

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'
Cl Cl 0.1484 0.1585 '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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'

_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'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   20.2414(19)
_cell_length_b                   20.2414(19)
_cell_length_c                   4.7009(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1926.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.371
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3266
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         24.966
_diffrn_reflns_theta_full        24.966
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             1547
_reflns_number_gt                1418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_max     0.799
_reflns_Friedel_fraction_full    0.799

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0463P)²+0.0217P] 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_abs_structure_details 
;
 Flack x determined using 466 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1547
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Cl1 Cl 0.47187(4) 0.91259(4) 0.9882(3) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.62256(11) 0.75283(11) 0.4830(7) 0.0232(6) Uani 1 1 d . . . . .
O2 O 0.60447(11) 0.64335(12) 0.4997(8) 0.0257(6) Uani 1 1 d . . . . .
N1 N 0.39059(15) 0.72076(15) 0.1132(7) 0.0182(7) Uani 1 1 d . . . . .
C10 C 0.58818(17) 0.70202(16) 0.4556(10) 0.0192(9) Uani 1 1 d . . . . .
C6 C 0.40995(18) 0.76617(18) 0.3196(9) 0.0179(8) Uani 1 1 d . . . . .
C1 C 0.47503(18) 0.76290(17) 0.4309(8) 0.0176(9) Uani 1 1 d . . . . .
C3 C 0.44949(18) 0.85546(19) 0.7308(8) 0.0186(9) Uani 1 1 d . . . . .
C4 C 0.38461(18) 0.85825(19) 0.6236(9) 0.0193(9) Uani 1 1 d . . . . .
H4 H 0.355175 0.889720 0.692193 0.023 Uiso 1 1 calc R U . . .
C11 C 0.32176(16) 0.72065(18) 0.0077(11) 0.0217(8) Uani 1 1 d . . . . .
H11A H 0.292557 0.707390 0.158127 0.032 Uiso 1 1 calc R U . . .
H11B H 0.317912 0.690250 -0.148215 0.032 Uiso 1 1 calc R U . . .
H11C H 0.310121 0.764230 -0.055396 0.032 Uiso 1 1 calc R U . . .
C9 C 0.51810(18) 0.71147(18) 0.3362(8) 0.0187(8) Uani 1 1 d . . . . .
C8 C 0.49549(19) 0.66826(19) 0.1300(9) 0.0218(9) Uani 1 1 d . . . . .
H8 H 0.523048 0.634803 0.064430 0.026 Uiso 1 1 calc R U . . .
C7 C 0.43177(17) 0.67430(17) 0.0193(10) 0.0201(8) Uani 1 1 d . . . . .
H7 H 0.417856 0.645410 -0.122396 0.024 Uiso 1 1 calc R U . . .
C5 C 0.36491(18) 0.81449(18) 0.4179(8) 0.0182(9) Uani 1 1 d . . . . .
H5 H 0.322368 0.816546 0.343693 0.022 Uiso 1 1 calc R U . . .
C2 C 0.49378(18) 0.80948(18) 0.6381(8) 0.0168(9) Uani 1 1 d . . . . .
H2 H 0.536406 0.808890 0.711876 0.020 Uiso 1 1 calc R 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
Cl1 C3 1.734(4) . ?
O1 C10 1.248(4) . ?
O2 C10 1.250(4) . ?
N1 C7 1.332(5) . ?
N1 C6 1.393(5) . ?
N1 C11 1.479(5) . ?
C10 C9 1.538(5) . ?
C6 C5 1.415(5) . ?
C6 C1 1.419(5) . ?
C1 C2 1.408(5) . ?
C1 C9 1.429(5) . ?
C3 C2 1.364(5) . ?
C3 C4 1.408(5) . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 C8 1.383(6) . ?
C8 C7 1.396(5) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?

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
C7 N1 C6 121.4(3) . . ?
C7 N1 C11 118.5(3) . . ?
C6 N1 C11 120.0(3) . . ?
O2 C10 O1 128.2(3) . . ?
O2 C10 C9 115.0(3) . . ?
O1 C10 C9 116.7(3) . . ?
N1 C6 C5 120.2(3) . . ?
N1 C6 C1 119.2(3) . . ?
C5 C6 C1 120.7(3) . . ?
C2 C1 C6 118.3(3) . . ?
C2 C1 C9 122.6(3) . . ?
C6 C1 C9 119.1(3) . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 Cl1 120.4(3) . . ?
C4 C3 Cl1 117.8(3) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 C1 118.5(3) . . ?
C8 C9 C10 118.9(3) . . ?
C1 C9 C10 122.7(3) . . ?
C9 C8 C7 120.8(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
N1 C7 C8 121.1(4) . . ?
N1 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.053




