# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_20170420JND_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2030808'
loop_
_audit_author_name
_audit_author_address
'Jie Li'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2020-09-08 deposited with the CCDC.	2021-05-07 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         ?
_chemical_formula_sum            'C16 H16 Cl N3 O2'
_chemical_formula_weight         317.77

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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   22.394(6)
_cell_length_b                   6.7389(18)
_cell_length_c                   11.449(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.142(7)
_cell_angle_gamma                90
_cell_volume                     1537.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3651
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      28.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.952
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5100
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.191
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1472
_reflns_number_gt                1055
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1743P)²+2.9285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1472
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.2854
_refine_ls_wR_factor_gt          0.2594
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
C1 C 0.8051(3) 0.5000 0.7453(6) 0.0396(15) Uani 1 2 d S T P . .
C2 C 0.8134(3) 0.5000 0.6343(6) 0.0389(15) Uani 1 2 d S T P . .
H2 H 0.8562 0.5000 0.6403 0.047 Uiso 1 2 calc R U P . .
C3 C 0.7568(3) 0.5000 0.5114(6) 0.0335(14) Uani 1 2 d S T P . .
C4 C 0.6910(3) 0.5000 0.5032(6) 0.0341(14) Uani 1 2 d S T P . .
C5 C 0.6855(3) 0.5000 0.6208(6) 0.0403(15) Uani 1 2 d S T P . .
H5 H 0.6432 0.5000 0.6171 0.048 Uiso 1 2 calc R U P . .
C6 C 0.7406(3) 0.5000 0.7396(6) 0.0411(16) Uani 1 2 d S T P . .
H6 H 0.7361 0.5000 0.8163 0.049 Uiso 1 2 calc R U P . .
C7 C 0.6337(3) 0.5000 0.3734(6) 0.0369(14) Uani 1 2 d S T P . .
C8 C 0.5059(3) 0.5000 0.2471(6) 0.0485(19) Uani 1 2 d S T P . .
C9 C 0.4974(3) 0.3155(11) 0.1666(6) 0.077(2) Uani 1 1 d . . . . .
H9A H 0.5305 0.3144 0.1351 0.116 Uiso 1 1 calc R U . . .
H9B H 0.4534 0.3143 0.0934 0.116 Uiso 1 1 calc R U . . .
H9C H 0.5031 0.2004 0.2201 0.116 Uiso 1 1 calc R U . . .
C10 C 0.4536(3) 0.5000 0.2987(8) 0.073(3) Uani 1 2 d S T P . .
H10A H 0.4653 0.4015 0.3662 0.109 Uiso 0.5 1 calc R U P . .
H10B H 0.4102 0.4701 0.2281 0.109 Uiso 0.5 1 calc R U P . .
H10C H 0.4525 0.6283 0.3341 0.109 Uiso 0.5 1 calc R U P . .
C11 C 0.7010(3) 0.5000 0.2765(6) 0.0337(14) Uani 1 2 d S T P . .
C12 C 0.7591(3) 0.5000 0.3905(6) 0.0339(14) Uani 1 2 d S T P . .
C13 C 0.8162(3) 0.5000 0.3604(6) 0.0401(15) Uani 1 2 d S T P . .
C14 C 0.7186(3) 0.5000 0.1649(6) 0.0429(16) Uani 1 2 d S T P . .
C15 C 0.8271(4) 0.5000 0.1494(7) 0.058(2) Uani 1 2 d S T P . .
H15A H 0.8082 0.4059 0.0789 0.088 Uiso 0.5 1 calc R U P . .
H15B H 0.8727 0.4641 0.2069 0.088 Uiso 0.5 1 calc R U P . .
H15C H 0.8261 0.6300 0.1142 0.088 Uiso 0.5 1 calc R U P . .
Cl1 Cl 0.87479(8) 0.5000 0.89794(15) 0.0553(7) Uani 1 2 d S T P . .
N1 N 0.5713(2) 0.5000 0.3655(5) 0.0485(16) Uani 1 2 d S T P . .
H1A H 0.5697 0.5000 0.4410 0.058 Uiso 1 2 d R U P . .
N2 N 0.6382(2) 0.5000 0.2622(5) 0.0386(13) Uani 1 2 d S T P . .
N3 N 0.7883(3) 0.5000 0.2223(5) 0.0430(14) Uani 1 2 d S T P . .
O1 O 0.6834(2) 0.5000 0.0484(4) 0.0604(15) Uani 1 2 d S T P . .
O2 O 0.8752(2) 0.5000 0.4327(5) 0.0627(16) Uani 1 2 d S T 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
C1 C2 1.366(9) . ?
C1 C6 1.414(9) . ?
C1 Cl1 1.733(6) . ?
C2 C3 1.400(8) . ?
C2 H2 0.9300 . ?
C3 C12 1.409(8) . ?
C3 C4 1.432(8) . ?
C4 C5 1.407(9) . ?
C4 C7 1.454(8) . ?
C5 C6 1.357(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.322(8) . ?
C7 N1 1.359(7) . ?
C8 N1 1.473(7) . ?
C8 C9 1.507(7) . ?
C8 C9 1.507(7) 6_565 ?
C8 C10 1.534(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.339(8) . ?
C11 C12 1.359(8) . ?
C11 C14 1.500(9) . ?
C12 C13 1.469(8) . ?
C13 O2 1.197(8) . ?
C13 N3 1.410(8) . ?
C14 O1 1.201(7) . ?
C14 N3 1.390(8) . ?
C15 N3 1.455(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1A 0.8825 . ?

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 C1 C6 121.7(6) . . ?
C2 C1 Cl1 119.7(5) . . ?
C6 C1 Cl1 118.5(5) . . ?
C1 C2 C3 119.3(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C12 124.4(5) . . ?
C2 C3 C4 119.9(5) . . ?
C12 C3 C4 115.6(5) . . ?
C5 C4 C3 118.2(5) . . ?
C5 C4 C7 123.8(6) . . ?
C3 C4 C7 118.0(5) . . ?
C6 C5 C4 121.5(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.3(6) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N2 C7 N1 117.6(5) . . ?
N2 C7 C4 124.4(5) . . ?
N1 C7 C4 118.0(5) . . ?
N1 C8 C9 110.9(4) . . ?
N1 C8 C9 110.9(4) . 6_565 ?
C9 C8 C9 111.2(7) . 6_565 ?
N1 C8 C10 105.0(5) . . ?
C9 C8 C10 109.3(4) . . ?
C9 C8 C10 109.3(4) 6_565 . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 127.6(6) . . ?
N2 C11 C14 124.4(5) . . ?
C12 C11 C14 108.0(5) . . ?
C11 C12 C3 119.7(5) . . ?
C11 C12 C13 109.3(5) . . ?
C3 C12 C13 131.0(5) . . ?
O2 C13 N3 124.1(6) . . ?
O2 C13 C12 130.0(6) . . ?
N3 C13 C12 105.9(5) . . ?
O1 C14 N3 123.4(6) . . ?
O1 C14 C11 130.8(6) . . ?
N3 C14 C11 105.8(5) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 128.5(5) . . ?
C7 N1 H1A 115.8 . . ?
C8 N1 H1A 115.7 . . ?
C7 N2 C11 114.7(5) . . ?
C14 N3 C13 111.0(5) . . ?
C14 N3 C15 124.4(6) . . ?
C13 N3 C15 124.6(5) . . ?

_refine_diff_density_max         1.167
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.096



