# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_211030d
_database_code_depnum_ccdc_archive 'CCDC 2121317'
loop_
_audit_author_name
_audit_author_address
'Qingxia Yao'
;Liaocheng University
China
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2021-12-13 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            'C17 H17 Cl N2 O2'
_chemical_formula_weight         316.77

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'
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                   10.2910(9)
_cell_length_b                   19.2325(17)
_cell_length_c                   8.6155(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.623(4)
_cell_angle_gamma                90
_cell_volume                     1562.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7672
_cell_measurement_theta_min      2.118
_cell_measurement_theta_max      25.013

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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  'fine-focus sealed tube'
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            7672
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_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             2744
_reflns_number_gt                1830
_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 1.171.39.29a (Rigaku Oxford Diffraction, 2015)'
_computing_cell_refinement       
'CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    SHELXL-2018/3
_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)+(0.0632P)²+0.5140P] 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         2744
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C12 C -0.0697(3) 0.52332(15) 0.1732(4) 0.0557(8) Uani 1 1 d . . . . .
H12A H 0.012205 0.516374 0.144092 0.084 Uiso 1 1 calc R U . . .
H12B H -0.044843 0.556520 0.267032 0.084 Uiso 1 1 calc R U . . .
H12C H -0.149405 0.541564 0.074526 0.084 Uiso 1 1 calc R U . . .
O2 O -0.10866(19) 0.45899(10) 0.2225(3) 0.0537(6) Uani 1 1 d . . . . .
C7 C -0.0516(3) 0.36076(14) 0.3905(3) 0.0414(7) Uani 1 1 d . . . . .
H7 H -0.147189 0.346304 0.331527 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0089(3) 0.42310(14) 0.3500(3) 0.0380(6) Uani 1 1 d . . . . .
Cl1 Cl 0.74947(9) 0.37216(5) 0.64858(15) 0.0808(4) Uani 1 1 d . . . . .
O1 O 0.4581(2) 0.27162(10) 0.9775(3) 0.0623(6) Uani 1 1 d . . . . .
N1 N 0.3758(2) 0.32182(11) 0.8604(3) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.1825(3) 0.33954(13) 0.6034(3) 0.0339(6) Uani 1 1 d . . . . .
C10 C 0.2258(2) 0.40320(12) 0.5597(3) 0.0336(6) Uani 1 1 d . . . . .
C2 C 0.2756(3) 0.29319(13) 0.7370(3) 0.0374(6) Uani 1 1 d . . . . .
C13 C 0.3758(2) 0.42761(12) 0.6372(3) 0.0351(6) Uani 1 1 d . . . . .
N2 N 0.6567(2) 0.47436(13) 0.7702(3) 0.0566(7) Uani 1 1 d . . . . .
C6 C 0.0411(3) 0.31855(13) 0.5148(3) 0.0392(6) Uani 1 1 d . . . . .
C14 C 0.4804(3) 0.39150(14) 0.6109(4) 0.0413(7) Uani 1 1 d . . . . .
H14 H 0.459535 0.349842 0.546258 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1303(3) 0.44419(13) 0.4353(3) 0.0390(6) Uani 1 1 d . . . . .
H9 H 0.160213 0.487429 0.407566 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6161(3) 0.41748(15) 0.6811(4) 0.0458(7) Uani 1 1 d . . . . .
C5 C -0.0039(3) 0.24897(15) 0.5530(4) 0.0526(8) Uani 1 1 d . . . . .
H5A H -0.092929 0.234435 0.458815 0.063 Uiso 1 1 calc R U . . .
H5B H -0.021828 0.251786 0.657520 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5533(3) 0.50937(16) 0.7913(4) 0.0618(9) Uani 1 1 d . . . . .
H16 H 0.577334 0.551496 0.853984 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1114(3) 0.19625(14) 0.5763(4) 0.0538(8) Uani 1 1 d . . . . .
H4A H 0.130064 0.193920 0.472277 0.065 Uiso 1 1 calc R U . . .
H4B H 0.080170 0.149688 0.596469 0.065 Uiso 1 1 calc R U . . .
C3 C 0.2458(3) 0.21687(14) 0.7256(4) 0.0495(7) Uani 1 1 d . . . . .
H3A H 0.238259 0.201542 0.831342 0.059 Uiso 1 1 calc R U . . .
H3B H 0.326979 0.192036 0.717158 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4137(3) 0.48840(14) 0.7280(4) 0.0524(8) Uani 1 1 d . . . . .
H17 H 0.344376 0.515653 0.746854 0.063 Uiso 1 1 calc R U . . .
C1 C 0.5781(4) 0.30457(18) 1.0997(5) 0.0825(12) Uani 1 1 d . . . . .
H1A H 0.547301 0.339608 1.160384 0.124 Uiso 1 1 calc R U . . .
H1B H 0.632817 0.327087 1.043319 0.124 Uiso 1 1 calc R U . . .
H1C H 0.637428 0.269870 1.180299 0.124 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
C12 O2 1.417(3) . ?
O2 C8 1.354(3) . ?
C7 C8 1.369(4) . ?
C7 C6 1.377(4) . ?
C8 C9 1.383(3) . ?
Cl1 C15 1.740(3) . ?
O1 N1 1.408(3) . ?
O1 C1 1.412(4) . ?
N1 C2 1.272(3) . ?
C11 C10 1.405(3) . ?
C11 C6 1.405(3) . ?
C11 C2 1.467(4) . ?
C10 C9 1.376(3) . ?
C10 C13 1.491(3) . ?
C2 C3 1.495(4) . ?
C13 C17 1.373(4) . ?
C13 C14 1.374(3) . ?
N2 C15 1.305(4) . ?
N2 C16 1.332(4) . ?
C6 C5 1.495(4) . ?
C14 C15 1.375(4) . ?
C5 C4 1.512(4) . ?
C16 C17 1.377(4) . ?
C4 C3 1.516(4) . ?

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
C8 O2 C12 118.3(2) . . ?
C8 C7 C6 121.4(2) . . ?
O2 C8 C7 115.9(2) . . ?
O2 C8 C9 124.6(2) . . ?
C7 C8 C9 119.4(2) . . ?
N1 O1 C1 108.8(2) . . ?
C2 N1 O1 110.8(2) . . ?
C10 C11 C6 118.4(2) . . ?
C10 C11 C2 124.2(2) . . ?
C6 C11 C2 117.4(2) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 C13 117.2(2) . . ?
C11 C10 C13 122.5(2) . . ?
N1 C2 C11 116.6(2) . . ?
N1 C2 C3 123.8(2) . . ?
C11 C2 C3 119.5(2) . . ?
C17 C13 C14 117.5(2) . . ?
C17 C13 C10 122.0(2) . . ?
C14 C13 C10 120.4(2) . . ?
C15 N2 C16 114.8(2) . . ?
C7 C6 C11 119.8(2) . . ?
C7 C6 C5 121.3(2) . . ?
C11 C6 C5 118.8(2) . . ?
C13 C14 C15 118.0(3) . . ?
C10 C9 C8 120.7(2) . . ?
N2 C15 C14 126.3(3) . . ?
N2 C15 Cl1 115.3(2) . . ?
C14 C15 Cl1 118.4(2) . . ?
C6 C5 C4 109.5(2) . . ?
N2 C16 C17 124.2(3) . . ?
C5 C4 C3 109.7(2) . . ?
C2 C3 C4 114.0(2) . . ?
C13 C17 C16 119.2(3) . . ?

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
_geom_hbond_publ_flag
C9 H9 Cl1 0.95 2.96 3.905(3) 174.3 3_666 yes
C9 H9 Cl1 0.95 2.96 3.905(3) 174.3 3_666 yes
C14 H14 O1 0.95 2.41 3.317(3) 160.0 4_565 yes
C9 H9 Cl1 0.95 2.96 3.905(3) 174.3 3_666 yes
C17 H17 O2 0.95 2.59 3.483(4) 156.8 3_566 yes
C14 H14 O1 0.95 2.41 3.317(3) 160.0 4_565 yes
C9 H9 Cl1 0.95 2.96 3.905(3) 174.3 3_666 yes
C17 H17 O2 0.95 2.59 3.483(4) 156.8 3_566 yes

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.051

