# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2095617'
loop_
_audit_author_name
_audit_author_address
'Zhenfeng Zhang'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Benzyl (R)-2-(4-fluorophenyl)morpholine-4-carboxylate'
_chemical_name_common            2b
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 F N O3'
_chemical_formula_sum            'C18 H18 F N O3'
_chemical_formula_weight         315.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.798(3)
_cell_length_b                   8.047(2)
_cell_length_c                   11.933(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.18(2)
_cell_angle_gamma                90
_cell_volume                     802.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6597
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      68.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   0.6720
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.801
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.896
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10998
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.899
_diffrn_reflns_theta_max         68.421
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2929
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.995

_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       ?
_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)+(0.0509P)²+0.0546P] 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 1162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2929
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.3747(2) 0.3166(2) 0.55309(12) 0.0651(4) Uani 1 1 d . . . . .
C1 C 0.1250(3) -0.1648(3) 0.6826(2) 0.0678(6) Uani 1 1 d . . . . .
N1 N 0.4611(3) 0.5493(2) 0.73571(16) 0.0689(6) Uani 1 1 d . . . . .
F1 F 0.0379(2) -0.3041(2) 0.68897(17) 0.0978(6) Uani 1 1 d . . . . .
O2 O 0.5358(2) 0.5971(2) 0.93195(14) 0.0762(5) Uani 1 1 d . . . . .
C2 C 0.1033(3) -0.0926(3) 0.5762(2) 0.0685(6) Uani 1 1 d . . . . .
H2 H 0.030241 -0.135530 0.508246 0.082 Uiso 1 1 calc R U . . .
O3 O 0.6212(2) 0.7621(2) 0.81118(14) 0.0674(4) Uani 1 1 d . . . . .
C3 C 0.1934(3) 0.0475(3) 0.57147(18) 0.0577(5) Uani 1 1 d . . . . .
H3 H 0.181670 0.097875 0.499124 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2999(2) 0.1129(3) 0.67226(17) 0.0518(5) Uani 1 1 d . . . . .
C7 C 0.3999(3) 0.2638(3) 0.67167(17) 0.0528(5) Uani 1 1 d . . . . .
H7 H 0.512830 0.233781 0.706453 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2274(3) -0.1041(3) 0.7845(2) 0.0724(6) Uani 1 1 d . . . . .
H6 H 0.238015 -0.155897 0.856168 0.087 Uiso 1 1 calc R U . . .
C5 C 0.3152(3) 0.0359(3) 0.7793(2) 0.0645(5) Uani 1 1 d . . . . .
H5 H 0.385416 0.079233 0.848371 0.077 Uiso 1 1 calc R U . . .
C9 C 0.4516(3) 0.5992(3) 0.61600(19) 0.0700(6) Uani 1 1 d . . . . .
H9A H 0.531421 0.683505 0.618736 0.084 Uiso 1 1 calc R U . . .
H9AB H 0.346877 0.645767 0.576316 0.084 Uiso 1 1 calc R U . . .
C8 C 0.3631(3) 0.4063(3) 0.7418(2) 0.0655(6) Uani 1 1 d . . . . .
H8A H 0.250774 0.435481 0.710299 0.079 Uiso 1 1 calc R U . . .
H8AB H 0.384537 0.372886 0.823406 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4798(3) 0.4499(3) 0.5495(2) 0.0677(6) Uani 1 1 d . . . . .
H10A H 0.463972 0.480612 0.468018 0.081 Uiso 1 1 calc R U . . .
H10B H 0.589696 0.413313 0.583377 0.081 Uiso 1 1 calc R U . . .
C11 C 0.5386(3) 0.6325(3) 0.83377(19) 0.0602(5) Uani 1 1 d . . . . .
C12 C 0.7086(4) 0.8581(4) 0.9126(2) 0.0771(7) Uani 1 1 d . . . . .
H12A H 0.797016 0.793199 0.962255 0.093 Uiso 1 1 calc R U . . .
H12B H 0.639023 0.887662 0.958524 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7705(3) 1.0117(3) 0.8715(2) 0.0654(6) Uani 1 1 d . . . . .
C14 C 0.8201(3) 1.0168(4) 0.7730(3) 0.0774(7) Uani 1 1 d . . . . .
H14 H 0.813009 0.921802 0.727306 0.093 Uiso 1 1 calc R U . . .
C15 C 0.8800(4) 1.1614(4) 0.7414(3) 0.0917(9) Uani 1 1 d . . . . .
H15 H 0.912522 1.163061 0.674397 0.110 Uiso 1 1 calc R U . . .
C16 C 0.8923(3) 1.3028(4) 0.8078(3) 0.0890(9) Uani 1 1 d . . . . .
H16 H 0.935655 1.399170 0.787307 0.107 Uiso 1 1 calc R U . . .
C17 C 0.8406(4) 1.3006(4) 0.9034(3) 0.0971(10) Uani 1 1 d . . . . .
H17 H 0.845860 1.396705 0.947716 0.117 Uiso 1 1 calc R U . . .
C18 C 0.7804(4) 1.1566(4) 0.9350(3) 0.0931(9) Uani 1 1 d . . . . .
H18 H 0.745528 1.157021 1.000967 0.112 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
O1 C10 1.426(3) . ?
O1 C7 1.427(2) . ?
C1 C2 1.355(4) . ?
C1 C6 1.358(4) . ?
C1 F1 1.374(3) . ?
N1 C11 1.336(3) . ?
N1 C8 1.454(3) . ?
N1 C9 1.461(3) . ?
O2 C11 1.214(3) . ?
C2 C3 1.389(3) . ?
O3 C11 1.345(3) . ?
O3 C12 1.440(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.388(3) . ?
C4 C7 1.501(3) . ?
C7 C8 1.513(3) . ?
C6 C5 1.378(4) . ?
C9 C10 1.503(4) . ?
C12 C13 1.494(4) . ?
C13 C14 1.376(4) . ?
C13 C18 1.378(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.371(5) . ?
C16 C17 1.353(5) . ?
C17 C18 1.375(5) . ?

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
C10 O1 C7 110.63(17) . . ?
C2 C1 C6 123.0(2) . . ?
C2 C1 F1 119.0(2) . . ?
C6 C1 F1 118.0(2) . . ?
C11 N1 C8 120.11(18) . . ?
C11 N1 C9 125.2(2) . . ?
C8 N1 C9 114.37(19) . . ?
C1 C2 C3 118.1(2) . . ?
C11 O3 C12 115.31(18) . . ?
C4 C3 C2 121.1(2) . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C7 123.03(18) . . ?
C5 C4 C7 118.50(19) . . ?
O1 C7 C4 109.60(17) . . ?
O1 C7 C8 109.24(18) . . ?
C4 C7 C8 112.55(17) . . ?
C1 C6 C5 118.6(2) . . ?
C6 C5 C4 120.8(2) . . ?
N1 C9 C10 109.2(2) . . ?
N1 C8 C7 109.84(18) . . ?
O1 C10 C9 111.71(19) . . ?
O2 C11 N1 124.7(2) . . ?
O2 C11 O3 123.4(2) . . ?
N1 C11 O3 111.90(18) . . ?
O3 C12 C13 108.8(2) . . ?
C14 C13 C18 117.5(3) . . ?
C14 C13 C12 123.4(2) . . ?
C18 C13 C12 119.1(2) . . ?
C13 C14 C15 120.6(3) . . ?
C16 C15 C14 120.7(3) . . ?
C17 C16 C15 119.3(3) . . ?
C16 C17 C18 120.1(3) . . ?
C17 C18 C13 121.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.7(4) . . . . ?
F1 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C7 180.0(2) . . . . ?
C10 O1 C7 C4 -174.40(18) . . . . ?
C10 O1 C7 C8 61.9(2) . . . . ?
C3 C4 C7 O1 -4.2(3) . . . . ?
C5 C4 C7 O1 176.0(2) . . . . ?
C3 C4 C7 C8 117.6(2) . . . . ?
C5 C4 C7 C8 -62.2(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
F1 C1 C6 C5 -179.8(2) . . . . ?
C1 C6 C5 C4 -0.3(4) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C7 C4 C5 C6 -179.3(2) . . . . ?
C11 N1 C9 C10 135.5(3) . . . . ?
C8 N1 C9 C10 -50.8(3) . . . . ?
C11 N1 C8 C7 -133.0(2) . . . . ?
C9 N1 C8 C7 52.9(3) . . . . ?
O1 C7 C8 N1 -56.8(3) . . . . ?
C4 C7 C8 N1 -178.79(18) . . . . ?
C7 O1 C10 C9 -61.4(3) . . . . ?
N1 C9 C10 O1 53.8(3) . . . . ?
C8 N1 C11 O2 0.8(4) . . . . ?
C9 N1 C11 O2 174.1(3) . . . . ?
C8 N1 C11 O3 -179.1(2) . . . . ?
C9 N1 C11 O3 -5.8(3) . . . . ?
C12 O3 C11 O2 0.2(4) . . . . ?
C12 O3 C11 N1 -179.8(2) . . . . ?
C11 O3 C12 C13 -170.6(2) . . . . ?
O3 C12 C13 C14 -34.6(4) . . . . ?
O3 C12 C13 C18 145.9(3) . . . . ?
C18 C13 C14 C15 1.2(4) . . . . ?
C12 C13 C14 C15 -178.2(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C15 C16 C17 C18 1.7(5) . . . . ?
C16 C17 C18 C13 -0.1(6) . . . . ?
C14 C13 C18 C17 -1.4(5) . . . . ?
C12 C13 C18 C17 178.1(3) . . . . ?

_refine_diff_density_max         0.094
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.021



####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 2095806'
loop_
_audit_author_name
_audit_author_address
'Zhenfeng Zhang'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-(6-(4-chlorophenyl)-2,3-dihydro-4H-1,4-oxazin-4-yl)-2-phenylethan-1-one
_chemical_name_common            1c
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N O3'
_chemical_formula_sum            'C18 H15 Cl N O3'
_chemical_formula_weight         328.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.5094(2)
_cell_length_b                   14.3271(4)
_cell_length_c                   19.9017(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1570.92(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      68.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   0.6407
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.280
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23942
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.801
_diffrn_reflns_theta_max         68.165
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2883
_reflns_number_gt                2642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       ?
_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)+(0.0607P)²+0.1779P] 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 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(8)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cl1 Cl 1.35435(17) 0.42215(8) 0.39217(4) 0.0730(3) Uani 1 1 d . . . . .
C1 C 1.1738(5) 0.4241(2) 0.46421(15) 0.0486(6) Uani 1 1 d . . . . .
N1 N 0.4356(5) 0.35459(16) 0.71238(12) 0.0467(6) Uani 1 1 d . . . . .
O1 O 0.7559(4) 0.50138(13) 0.67936(10) 0.0502(5) Uani 1 1 d . . . . .
O3 O 0.1244(4) 0.30019(13) 0.77283(10) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.8223(6) 0.3715(2) 0.52245(15) 0.0502(7) Uani 1 1 d . . . . .
H3 H 0.681212 0.335933 0.523406 0.060 Uiso 1 1 calc R U . . .
O2 O 0.2933(5) 0.20805(15) 0.69310(11) 0.0596(6) Uani 1 1 d . . . . .
C2 C 0.9639(6) 0.3714(2) 0.46505(15) 0.0511(7) Uani 1 1 d . . . . .
H2 H 0.918522 0.336484 0.427713 0.061 Uiso 1 1 calc R U . . .
C6 C 1.2391(6) 0.4784(2) 0.51805(16) 0.0535(7) Uani 1 1 d . . . . .
H6 H 1.379062 0.514577 0.516304 0.064 Uiso 1 1 calc R U . . .
C5 C 1.0947(5) 0.4787(2) 0.57504(15) 0.0484(7) Uani 1 1 d . . . . .
H5 H 1.137744 0.516176 0.611285 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8861(5) 0.42392(19) 0.57911(13) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.7363(5) 0.42239(18) 0.64026(13) 0.0418(6) Uani 1 1 d . . . . .
C9 C 0.4312(6) 0.4413(2) 0.75076(15) 0.0488(7) Uani 1 1 d . . . . .
H9A H 0.387944 0.428506 0.797102 0.059 Uiso 1 1 calc R U . . .
H9AB H 0.311390 0.483514 0.732059 0.059 Uiso 1 1 calc R U . . .
C8 C 0.5923(6) 0.3513(2) 0.65672(14) 0.0457(6) Uani 1 1 d . . . . .
C10 C 0.6794(6) 0.4850(2) 0.74755(14) 0.0501(7) Uani 1 1 d . . . . .
H10A H 0.677190 0.543823 0.771707 0.060 Uiso 1 1 calc R U . . .
H10B H 0.795525 0.444286 0.769513 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2852(6) 0.28122(18) 0.72347(14) 0.0445(6) Uani 1 1 d . . . . .
C12 C -0.0372(6) 0.2244(2) 0.78885(16) 0.0487(7) Uani 1 1 d . . . . .
H12A H 0.055859 0.169999 0.802193 0.058 Uiso 1 1 calc R U . . .
H12B H -0.132833 0.208078 0.749646 0.058 Uiso 1 1 calc R U . . .
C13 C -0.2020(5) 0.25372(19) 0.84519(14) 0.0421(6) Uani 1 1 d . . . . .
C14 C -0.4018(5) 0.1982(2) 0.85908(15) 0.0482(6) Uani 1 1 d . . . . .
H14 H -0.429449 0.144865 0.833538 0.058 Uiso 1 1 calc R U . . .
C15 C -0.5609(6) 0.2209(2) 0.91047(17) 0.0547(8) Uani 1 1 d . . . . .
H15 H -0.692759 0.182490 0.919755 0.066 Uiso 1 1 calc R U . . .
C16 C -0.5228(6) 0.3007(2) 0.94778(17) 0.0554(8) Uani 1 1 d . . . . .
H16 H -0.629859 0.316673 0.982023 0.066 Uiso 1 1 calc R U . . .
C17 C -0.3245(6) 0.3569(2) 0.93403(15) 0.0518(7) Uani 1 1 d . . . . .
H17 H -0.299184 0.410974 0.958859 0.062 Uiso 1 1 calc R U . . .
C18 C -0.1640(5) 0.3329(2) 0.88358(14) 0.0462(6) Uani 1 1 d . . . . .
H18 H -0.029259 0.370243 0.875347 0.055 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 C1 1.745(3) . ?
C1 C6 1.372(5) . ?
C1 C2 1.381(4) . ?
N1 C11 1.357(4) . ?
N1 C8 1.405(4) . ?
N1 C9 1.458(4) . ?
O1 C7 1.378(3) . ?
O1 C10 1.440(3) . ?
O3 C11 1.350(3) . ?
O3 C12 1.440(3) . ?
C3 C2 1.383(4) . ?
C3 C4 1.399(4) . ?
O2 C11 1.211(3) . ?
C6 C5 1.386(4) . ?
C5 C4 1.394(4) . ?
C4 C7 1.471(4) . ?
C7 C8 1.331(4) . ?
C9 C10 1.506(5) . ?
C12 C13 1.503(4) . ?
C13 C18 1.383(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.379(5) . ?
C16 C17 1.384(5) . ?
C17 C18 1.381(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
C6 C1 C2 121.3(3) . . ?
C6 C1 Cl1 120.1(2) . . ?
C2 C1 Cl1 118.6(2) . . ?
C11 N1 C8 118.6(2) . . ?
C11 N1 C9 124.4(2) . . ?
C8 N1 C9 116.8(2) . . ?
C7 O1 C10 112.1(2) . . ?
C11 O3 C12 114.5(2) . . ?
C2 C3 C4 121.6(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C6 C5 119.4(3) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C7 121.2(2) . . ?
C8 C7 O1 122.4(2) . . ?
C8 C7 C4 123.3(2) . . ?
O1 C7 C4 114.3(2) . . ?
N1 C9 C10 108.5(2) . . ?
C7 C8 N1 122.3(3) . . ?
O1 C10 C9 111.9(2) . . ?
O2 C11 O3 124.2(3) . . ?
O2 C11 N1 124.5(3) . . ?
O3 C11 N1 111.3(2) . . ?
O3 C12 C13 109.1(2) . . ?
C18 C13 C14 118.7(3) . . ?
C18 C13 C12 123.4(3) . . ?
C14 C13 C12 117.9(3) . . ?
C15 C14 C13 121.0(3) . . ?
C16 C15 C14 119.7(3) . . ?
C15 C16 C17 119.7(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 C13 120.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.2(5) . . . . ?
Cl1 C1 C2 C3 179.0(2) . . . . ?
C4 C3 C2 C1 0.4(5) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Cl1 C1 C6 C5 -179.6(2) . . . . ?
C1 C6 C5 C4 0.9(5) . . . . ?
C6 C5 C4 C3 -2.6(4) . . . . ?
C6 C5 C4 C7 178.4(3) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C4 C7 -179.0(3) . . . . ?
C10 O1 C7 C8 20.7(4) . . . . ?
C10 O1 C7 C4 -159.6(2) . . . . ?
C5 C4 C7 C8 -155.7(3) . . . . ?
C3 C4 C7 C8 25.4(4) . . . . ?
C5 C4 C7 O1 24.7(4) . . . . ?
C3 C4 C7 O1 -154.3(3) . . . . ?
C11 N1 C9 C10 154.3(3) . . . . ?
C8 N1 C9 C10 -31.6(4) . . . . ?
O1 C7 C8 N1 5.0(5) . . . . ?
C4 C7 C8 N1 -174.6(3) . . . . ?
C11 N1 C8 C7 176.4(3) . . . . ?
C9 N1 C8 C7 1.9(4) . . . . ?
C7 O1 C10 C9 -52.0(3) . . . . ?
N1 C9 C10 O1 57.0(3) . . . . ?
C12 O3 C11 O2 1.8(4) . . . . ?
C12 O3 C11 N1 -178.3(3) . . . . ?
C8 N1 C11 O2 8.4(5) . . . . ?
C9 N1 C11 O2 -177.6(3) . . . . ?
C8 N1 C11 O3 -171.6(2) . . . . ?
C9 N1 C11 O3 2.5(4) . . . . ?
C11 O3 C12 C13 178.8(2) . . . . ?
O3 C12 C13 C18 -12.6(4) . . . . ?
O3 C12 C13 C14 167.4(2) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 C13 1.4(4) . . . . ?
C14 C13 C18 C17 -1.1(4) . . . . ?
C12 C13 C18 C17 178.9(3) . . . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.040



