# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cu_20240224_lx3_151_2_0m_pl
_audit_block_doi                 10.5517/ccdc.csd.cc2mpp01
_database_code_depnum_ccdc_archive 'CCDC 2433903'
loop_
_audit_author_name
_audit_author_address
'XIN LI'
;FUDAN university
China
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-10-17 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            'C19 H19 N O2'
_chemical_formula_weight         293.35

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'

_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                   21.821(9)
_cell_length_b                   8.608(3)
_cell_length_c                   8.127(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.229(17)
_cell_angle_gamma                90
_cell_volume                     1520.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6099
_cell_measurement_theta_min      4.0672
_cell_measurement_theta_max      64.7582

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  d8_venture
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28991
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.069
_diffrn_reflns_theta_max         65.397
_diffrn_reflns_theta_full        65.397
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2589
_reflns_number_gt                1914
_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       ?
_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)+(0.1442P)²+3.2515P] 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         2589
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.2937
_refine_ls_wR_factor_gt          0.2725
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.005

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 0.98187(15) -0.5393(5) 0.6978(6) 0.0947(14) Uani 1 1 d . . . . .
O1D O 0.54762(19) -0.6765(6) 0.9651(5) 0.1016(15) Uani 1 1 d . . . . .
N2 N 0.61995(16) -0.4949(5) 0.9126(5) 0.0599(10) Uani 1 1 d . . . . .
C1 C 0.5324(2) -0.5046(9) 0.7284(7) 0.0870(18) Uani 1 1 d . . . . .
H1 H 0.516143 -0.586597 0.655101 0.104 Uiso 1 1 calc R U . . .
H16 H 0.498621 -0.439131 0.755984 0.104 Uiso 1 1 calc R U . . .
C2 C 0.5793(2) -0.4111(8) 0.6488(7) 0.0848(17) Uani 1 1 d . . . . .
H14 H 0.561573 -0.314256 0.606147 0.102 Uiso 1 1 calc R U . . .
H15 H 0.594600 -0.468523 0.558308 0.102 Uiso 1 1 calc R U . . .
C3 C 0.6313(2) -0.3798(6) 0.7842(6) 0.0626(12) Uani 1 1 d . . . . .
H17 H 0.627558 -0.274387 0.827764 0.075 Uiso 1 1 calc R U . . .
C4 C 0.69517(19) -0.4043(6) 0.7325(6) 0.0630(12) Uani 1 1 d . . . . .
H12 H 0.702449 -0.331382 0.645388 0.076 Uiso 1 1 calc R U . . .
H13 H 0.698321 -0.508485 0.688672 0.076 Uiso 1 1 calc R U . . .
C5 C 0.7441(2) -0.3821(6) 0.8766(6) 0.0590(11) Uani 1 1 d . . . . .
H5 H 0.744198 -0.271436 0.905022 0.071 Uiso 1 1 calc R U . . .
C6 C 0.80815(19) -0.4208(5) 0.8300(5) 0.0566(11) Uani 1 1 d . . . . .
C7 C 0.8196(2) -0.5565(6) 0.7467(6) 0.0643(12) Uani 1 1 d . . . . .
H8 H 0.787347 -0.624937 0.718789 0.077 Uiso 1 1 calc R U . . .
C8 C 0.8778(2) -0.5927(6) 0.7040(7) 0.0720(14) Uani 1 1 d . . . . .
H7 H 0.884387 -0.684279 0.647587 0.086 Uiso 1 1 calc R U . . .
C9 C 0.9264(2) -0.4914(6) 0.7457(7) 0.0690(13) Uani 1 1 d . . . . .
C10 C 1.0332(2) -0.4393(8) 0.7321(9) 0.099(2) Uani 1 1 d . . . . .
H2 H 1.035913 -0.408775 0.846167 0.148 Uiso 1 1 calc R U . . .
H9 H 1.028302 -0.348697 0.663346 0.148 Uiso 1 1 calc R U . . .
H10 H 1.070191 -0.492910 0.710099 0.148 Uiso 1 1 calc R U . . .
C11 C 0.5656(2) -0.5715(7) 0.8814(6) 0.0707(13) Uani 1 1 d . . . . .
C12 C 0.66610(19) -0.5204(5) 1.0447(5) 0.0533(10) Uani 1 1 d . . . . .
C13 C 0.6515(2) -0.5951(6) 1.1896(6) 0.0659(12) Uani 1 1 d . . . . .
H19 H 0.611585 -0.629478 1.199348 0.079 Uiso 1 1 calc R U . . .
C14 C 0.6966(3) -0.6172(6) 1.3171(6) 0.0691(13) Uani 1 1 d . . . . .
H3 H 0.686838 -0.665766 1.413534 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7559(3) -0.5682(6) 1.3036(6) 0.0731(14) Uani 1 1 d . . . . .
H4 H 0.786094 -0.583223 1.390488 0.088 Uiso 1 1 calc R U . . .
C16 C 0.7702(2) -0.4967(6) 1.1605(6) 0.0661(12) Uani 1 1 d . . . . .
H18 H 0.810438 -0.464537 1.151622 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7263(2) -0.4714(5) 1.0299(5) 0.0550(11) Uani 1 1 d . . . . .
C18 C 0.8572(2) -0.3227(6) 0.8713(6) 0.0644(12) Uani 1 1 d . . . . .
H6 H 0.850658 -0.231285 0.928162 0.077 Uiso 1 1 calc R U . . .
C19 C 0.9166(2) -0.3571(6) 0.8297(7) 0.0731(14) Uani 1 1 d . . . . .
H11 H 0.949063 -0.289554 0.858888 0.088 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 C9 1.369(6) . ?
O1 C10 1.421(7) . ?
O1D C11 1.217(6) . ?
N2 C11 1.361(6) . ?
N2 C12 1.421(6) . ?
N2 C3 1.476(6) . ?
C1 C2 1.495(8) . ?
C1 C11 1.497(8) . ?
C1 H1 0.9700 . ?
C1 H16 0.9700 . ?
C2 C3 1.532(7) . ?
C2 H14 0.9700 . ?
C2 H15 0.9700 . ?
C3 C4 1.506(6) . ?
C3 H17 0.9800 . ?
C4 C5 1.523(6) . ?
C4 H12 0.9700 . ?
C4 H13 0.9700 . ?
C5 C6 1.518(6) . ?
C5 C17 1.543(6) . ?
C5 H5 0.9800 . ?
C6 C7 1.384(7) . ?
C6 C18 1.381(6) . ?
C7 C8 1.382(6) . ?
C7 H8 0.9300 . ?
C8 C9 1.391(7) . ?
C8 H7 0.9300 . ?
C9 C19 1.369(7) . ?
C10 H2 0.9600 . ?
C10 H9 0.9600 . ?
C10 H10 0.9600 . ?
C12 C17 1.395(6) . ?
C12 C13 1.404(6) . ?
C13 C14 1.375(7) . ?
C13 H19 0.9300 . ?
C14 C15 1.375(7) . ?
C14 H3 0.9300 . ?
C15 C16 1.376(7) . ?
C15 H4 0.9300 . ?
C16 C17 1.381(6) . ?
C16 H18 0.9300 . ?
C18 C19 1.401(7) . ?
C18 H6 0.9300 . ?
C19 H11 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
C9 O1 C10 117.6(5) . . ?
C11 N2 C12 127.7(4) . . ?
C11 N2 C3 113.2(4) . . ?
C12 N2 C3 119.0(4) . . ?
C2 C1 C11 105.6(4) . . ?
C2 C1 H1 110.6 . . ?
C11 C1 H1 110.6 . . ?
C2 C1 H16 110.6 . . ?
C11 C1 H16 110.6 . . ?
H1 C1 H16 108.8 . . ?
C1 C2 C3 106.0(4) . . ?
C1 C2 H14 110.5 . . ?
C3 C2 H14 110.5 . . ?
C1 C2 H15 110.5 . . ?
C3 C2 H15 110.5 . . ?
H14 C2 H15 108.7 . . ?
N2 C3 C4 108.8(4) . . ?
N2 C3 C2 103.2(4) . . ?
C4 C3 C2 114.8(4) . . ?
N2 C3 H17 109.9 . . ?
C4 C3 H17 109.9 . . ?
C2 C3 H17 109.9 . . ?
C3 C4 C5 111.7(4) . . ?
C3 C4 H12 109.3 . . ?
C5 C4 H12 109.3 . . ?
C3 C4 H13 109.3 . . ?
C5 C4 H13 109.3 . . ?
H12 C4 H13 107.9 . . ?
C6 C5 C4 112.2(4) . . ?
C6 C5 C17 113.4(4) . . ?
C4 C5 C17 110.3(4) . . ?
C6 C5 H5 106.8 . . ?
C4 C5 H5 106.8 . . ?
C17 C5 H5 106.8 . . ?
C7 C6 C18 117.7(4) . . ?
C7 C6 C5 121.2(4) . . ?
C18 C6 C5 121.1(4) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H8 119.2 . . ?
C8 C7 H8 119.2 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H7 120.2 . . ?
C9 C8 H7 120.2 . . ?
C19 C9 O1 125.3(5) . . ?
C19 C9 C8 120.1(5) . . ?
O1 C9 C8 114.6(5) . . ?
O1 C10 H2 109.5 . . ?
O1 C10 H9 109.5 . . ?
H2 C10 H9 109.5 . . ?
O1 C10 H10 109.5 . . ?
H2 C10 H10 109.5 . . ?
H9 C10 H10 109.5 . . ?
O1D C11 N2 125.2(5) . . ?
O1D C11 C1 126.4(5) . . ?
N2 C11 C1 108.4(5) . . ?
C17 C12 C13 119.9(4) . . ?
C17 C12 N2 119.7(4) . . ?
C13 C12 N2 120.4(4) . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H19 120.2 . . ?
C12 C13 H19 120.2 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H3 119.6 . . ?
C13 C14 H3 119.6 . . ?
C16 C15 C14 119.5(5) . . ?
C16 C15 H4 120.3 . . ?
C14 C15 H4 120.3 . . ?
C15 C16 C17 121.7(5) . . ?
C15 C16 H18 119.2 . . ?
C17 C16 H18 119.2 . . ?
C16 C17 C12 118.6(4) . . ?
C16 C17 C5 119.4(4) . . ?
C12 C17 C5 121.9(4) . . ?
C6 C18 C19 121.7(5) . . ?
C6 C18 H6 119.1 . . ?
C19 C18 H6 119.1 . . ?
C9 C19 C18 119.2(4) . . ?
C9 C19 H11 120.4 . . ?
C18 C19 H11 120.4 . . ?

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
C11 C1 C2 C3 -19.2(7) . . . . ?
C11 N2 C3 C4 -130.5(5) . . . . ?
C12 N2 C3 C4 45.8(5) . . . . ?
C11 N2 C3 C2 -8.2(5) . . . . ?
C12 N2 C3 C2 168.1(4) . . . . ?
C1 C2 C3 N2 16.8(6) . . . . ?
C1 C2 C3 C4 135.0(5) . . . . ?
N2 C3 C4 C5 -61.0(5) . . . . ?
C2 C3 C4 C5 -176.0(4) . . . . ?
C3 C4 C5 C6 174.8(4) . . . . ?
C3 C4 C5 C17 47.3(5) . . . . ?
C4 C5 C6 C7 -47.7(6) . . . . ?
C17 C5 C6 C7 78.1(6) . . . . ?
C4 C5 C6 C18 133.1(5) . . . . ?
C17 C5 C6 C18 -101.0(5) . . . . ?
C18 C6 C7 C8 -0.8(7) . . . . ?
C5 C6 C7 C8 -179.9(5) . . . . ?
C6 C7 C8 C9 0.3(8) . . . . ?
C10 O1 C9 C19 -2.5(9) . . . . ?
C10 O1 C9 C8 178.2(5) . . . . ?
C7 C8 C9 C19 0.5(8) . . . . ?
C7 C8 C9 O1 179.8(5) . . . . ?
C12 N2 C11 O1D 0.3(9) . . . . ?
C3 N2 C11 O1D 176.3(5) . . . . ?
C12 N2 C11 C1 -179.8(4) . . . . ?
C3 N2 C11 C1 -3.8(6) . . . . ?
C2 C1 C11 O1D -165.5(6) . . . . ?
C2 C1 C11 N2 14.6(7) . . . . ?
C11 N2 C12 C17 158.3(5) . . . . ?
C3 N2 C12 C17 -17.4(6) . . . . ?
C11 N2 C12 C13 -21.3(7) . . . . ?
C3 N2 C12 C13 162.9(4) . . . . ?
C17 C12 C13 C14 1.1(7) . . . . ?
N2 C12 C13 C14 -179.2(4) . . . . ?
C12 C13 C14 C15 -0.6(8) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
C15 C16 C17 C12 -0.1(7) . . . . ?
C15 C16 C17 C5 176.4(5) . . . . ?
C13 C12 C17 C16 -0.7(7) . . . . ?
N2 C12 C17 C16 179.6(4) . . . . ?
C13 C12 C17 C5 -177.1(4) . . . . ?
N2 C12 C17 C5 3.2(6) . . . . ?
C6 C5 C17 C16 38.3(6) . . . . ?
C4 C5 C17 C16 165.1(4) . . . . ?
C6 C5 C17 C12 -145.4(4) . . . . ?
C4 C5 C17 C12 -18.5(6) . . . . ?
C7 C6 C18 C19 0.6(7) . . . . ?
C5 C6 C18 C19 179.7(4) . . . . ?
O1 C9 C19 C18 -179.9(5) . . . . ?
C8 C9 C19 C18 -0.6(8) . . . . ?
C6 C18 C19 C9 0.1(8) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_cu_20240418_lx4_64_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2433902'
loop_
_audit_author_name
_audit_author_address
'XIN LI'
;FUDAN university
China
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-10-17 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            'C18 H16 Cl N O'
_chemical_formula_weight         297.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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                   7.1512(4)
_cell_length_b                   11.1221(6)
_cell_length_c                   9.7789(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.442(3)
_cell_angle_gamma                90
_cell_volume                     749.70(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    5506
_cell_measurement_theta_min      4.6913
_cell_measurement_theta_max      65.0570

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.226
_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      301(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9245
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.691
_diffrn_reflns_theta_max         65.052
_diffrn_reflns_theta_full        65.052
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.875
_reflns_number_total             2246
_reflns_number_gt                2023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.737
_reflns_Friedel_fraction_full    0.738

_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)+(0.0586P)²+0.1090P] 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 704 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.317(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2246
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 -0.06423(17) 0.08821(10) 0.10074(13) 0.0832(4) Uani 1 1 d . . . . .
O1 O 0.4444(6) 0.9129(4) 0.1513(5) 0.1032(14) Uani 1 1 d . . . . .
N1 N 0.4394(4) 0.7137(3) 0.2141(3) 0.0450(6) Uani 1 1 d . . . . .
C1 C 0.6206(8) 0.7618(5) 0.0575(6) 0.0843(15) Uani 1 1 d . . . . .
H8 H 0.731441 0.814182 0.065507 0.101 Uiso 1 1 calc R U . . .
H1 H 0.549173 0.755940 -0.041592 0.101 Uiso 1 1 calc R U . . .
C2G C 0.3159(4) 0.7162(4) 0.3065(3) 0.0453(7) Uani 1 1 d . . . . .
C2 C 0.6849(6) 0.6393(4) 0.1176(5) 0.0648(11) Uani 1 1 d . . . . .
H7 H 0.810035 0.643684 0.187098 0.078 Uiso 1 1 calc R U . . .
H6 H 0.694187 0.583882 0.043034 0.078 Uiso 1 1 calc R U . . .
C3 C 0.5265(4) 0.5996(3) 0.1871(3) 0.0459(7) Uani 1 1 d . . . . .
H13 H 0.429112 0.552081 0.118967 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5952(5) 0.5301(4) 0.3227(4) 0.0533(8) Uani 1 1 d . . . . .
H5 H 0.694437 0.575762 0.389433 0.064 Uiso 1 1 calc R U . . .
H14 H 0.652224 0.454761 0.304032 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4275(5) 0.5045(3) 0.3874(3) 0.0508(8) Uani 1 1 d . . . . .
H15 H 0.483991 0.478979 0.485690 0.061 Uiso 1 1 calc R U . . .
C6 C 0.3004(5) 0.4011(3) 0.3111(3) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.1168(5) 0.4186(3) 0.2202(4) 0.0479(8) Uani 1 1 d . . . . .
H16 H 0.067497 0.496176 0.203600 0.057 Uiso 1 1 calc R U . . .
C8 C 0.0067(5) 0.3231(4) 0.1542(4) 0.0506(8) Uani 1 1 d . . . . .
H2 H -0.115734 0.336316 0.093357 0.061 Uiso 1 1 calc R U . . .
C9 C 0.0778(5) 0.2087(3) 0.1783(3) 0.0479(8) Uani 1 1 d . . . . .
C10 C 0.3694(5) 0.2845(3) 0.3309(4) 0.0515(8) Uani 1 1 d . . . . .
H3 H 0.492790 0.271020 0.390147 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2612(5) 0.1874(3) 0.2657(4) 0.0536(9) Uani 1 1 d . . . . .
H4 H 0.310573 0.109731 0.280285 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4926(6) 0.8088(4) 0.1450(5) 0.0631(10) Uani 1 1 d . . . . .
C13 C 0.2001(6) 0.8164(4) 0.3102(5) 0.0621(10) Uani 1 1 d . . . . .
H12 H 0.201298 0.881499 0.250815 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0839(7) 0.8184(5) 0.4022(6) 0.0828(16) Uani 1 1 d . . . . .
H9 H 0.006205 0.885100 0.404231 0.099 Uiso 1 1 calc R U . . .
C15 C 0.0815(7) 0.7239(6) 0.4901(6) 0.0860(17) Uani 1 1 d . . . . .
H10 H 0.004605 0.726875 0.553178 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1935(6) 0.6235(5) 0.4855(4) 0.0710(13) Uani 1 1 d . . . . .
H11 H 0.190047 0.559127 0.545489 0.085 Uiso 1 1 calc R U . . .
C17 C 0.3127(5) 0.6165(3) 0.3923(3) 0.0491(8) 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
Cl1 C9 1.730(4) . ?
O1 C12 1.214(6) . ?
N1 C12 1.363(5) . ?
N1 C2G 1.422(4) . ?
N1 C3 1.469(5) . ?
C1 C12 1.503(6) . ?
C1 C2 1.507(7) . ?
C1 H8 0.9700 . ?
C1 H1 0.9700 . ?
C2G C13 1.394(6) . ?
C2G C17 1.394(5) . ?
C2 C3 1.533(5) . ?
C2 H7 0.9700 . ?
C2 H6 0.9700 . ?
C3 C4 1.500(5) . ?
C3 H13 0.9800 . ?
C4 C5 1.525(5) . ?
C4 H5 0.9700 . ?
C4 H14 0.9700 . ?
C5 C17 1.499(5) . ?
C5 C6 1.532(5) . ?
C5 H15 0.9800 . ?
C6 C10 1.382(5) . ?
C6 C7 1.389(4) . ?
C7 C8 1.376(5) . ?
C7 H16 0.9300 . ?
C8 C9 1.367(6) . ?
C8 H2 0.9300 . ?
C9 C11 1.382(5) . ?
C10 C11 1.382(5) . ?
C10 H3 0.9300 . ?
C11 H4 0.9300 . ?
C13 C14 1.378(6) . ?
C13 H12 0.9300 . ?
C14 C15 1.361(9) . ?
C14 H9 0.9300 . ?
C15 C16 1.382(8) . ?
C15 H10 0.9300 . ?
C16 C17 1.406(5) . ?
C16 H11 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
C12 N1 C2G 127.1(3) . . ?
C12 N1 C3 113.2(3) . . ?
C2G N1 C3 119.8(3) . . ?
C12 C1 C2 105.2(4) . . ?
C12 C1 H8 110.7 . . ?
C2 C1 H8 110.7 . . ?
C12 C1 H1 110.7 . . ?
C2 C1 H1 110.7 . . ?
H8 C1 H1 108.8 . . ?
C13 C2G C17 121.0(3) . . ?
C13 C2G N1 120.4(3) . . ?
C17 C2G N1 118.6(3) . . ?
C1 C2 C3 104.4(3) . . ?
C1 C2 H7 110.9 . . ?
C3 C2 H7 110.9 . . ?
C1 C2 H6 110.9 . . ?
C3 C2 H6 110.9 . . ?
H7 C2 H6 108.9 . . ?
N1 C3 C4 109.9(3) . . ?
N1 C3 C2 103.3(3) . . ?
C4 C3 C2 115.7(3) . . ?
N1 C3 H13 109.2 . . ?
C4 C3 H13 109.2 . . ?
C2 C3 H13 109.2 . . ?
C3 C4 C5 110.8(3) . . ?
C3 C4 H5 109.5 . . ?
C5 C4 H5 109.5 . . ?
C3 C4 H14 109.5 . . ?
C5 C4 H14 109.5 . . ?
H5 C4 H14 108.1 . . ?
C17 C5 C4 110.9(3) . . ?
C17 C5 C6 112.4(3) . . ?
C4 C5 C6 111.6(3) . . ?
C17 C5 H15 107.2 . . ?
C4 C5 H15 107.2 . . ?
C6 C5 H15 107.2 . . ?
C10 C6 C7 117.5(3) . . ?
C10 C6 C5 119.5(3) . . ?
C7 C6 C5 122.9(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H16 119.4 . . ?
C6 C7 H16 119.4 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H2 120.1 . . ?
C7 C8 H2 120.1 . . ?
C8 C9 C11 120.9(3) . . ?
C8 C9 Cl1 119.8(3) . . ?
C11 C9 Cl1 119.3(3) . . ?
C11 C10 C6 122.2(3) . . ?
C11 C10 H3 118.9 . . ?
C6 C10 H3 118.9 . . ?
C10 C11 C9 118.3(3) . . ?
C10 C11 H4 120.8 . . ?
C9 C11 H4 120.8 . . ?
O1 C12 N1 126.4(4) . . ?
O1 C12 C1 125.8(4) . . ?
N1 C12 C1 107.8(4) . . ?
C14 C13 C2G 119.7(5) . . ?
C14 C13 H12 120.1 . . ?
C2G C13 H12 120.1 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H9 119.6 . . ?
C13 C14 H9 119.6 . . ?
C14 C15 C16 119.9(4) . . ?
C14 C15 H10 120.0 . . ?
C16 C15 H10 120.0 . . ?
C15 C16 C17 121.5(4) . . ?
C15 C16 H11 119.3 . . ?
C17 C16 H11 119.3 . . ?
C2G C17 C16 117.1(4) . . ?
C2G C17 C5 123.0(3) . . ?
C16 C17 C5 119.9(4) . . ?

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
C12 N1 C2G C13 14.8(5) . . . . ?
C3 N1 C2G C13 -166.3(3) . . . . ?
C12 N1 C2G C17 -165.6(4) . . . . ?
C3 N1 C2G C17 13.4(4) . . . . ?
C12 C1 C2 C3 24.5(5) . . . . ?
C12 N1 C3 C4 137.3(3) . . . . ?
C2G N1 C3 C4 -41.8(4) . . . . ?
C12 N1 C3 C2 13.3(4) . . . . ?
C2G N1 C3 C2 -165.8(3) . . . . ?
C1 C2 C3 N1 -22.8(4) . . . . ?
C1 C2 C3 C4 -143.0(4) . . . . ?
N1 C3 C4 C5 59.0(4) . . . . ?
C2 C3 C4 C5 175.5(3) . . . . ?
C3 C4 C5 C17 -48.5(4) . . . . ?
C3 C4 C5 C6 77.6(4) . . . . ?
C17 C5 C6 C10 -161.9(3) . . . . ?
C4 C5 C6 C10 72.8(4) . . . . ?
C17 C5 C6 C7 18.7(4) . . . . ?
C4 C5 C6 C7 -106.5(4) . . . . ?
C10 C6 C7 C8 1.0(5) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C11 -1.5(5) . . . . ?
C7 C8 C9 Cl1 177.5(3) . . . . ?
C7 C6 C10 C11 -1.0(5) . . . . ?
C5 C6 C10 C11 179.6(3) . . . . ?
C6 C10 C11 C9 -0.2(5) . . . . ?
C8 C9 C11 C10 1.5(5) . . . . ?
Cl1 C9 C11 C10 -177.5(3) . . . . ?
C2G N1 C12 O1 0.5(8) . . . . ?
C3 N1 C12 O1 -178.5(5) . . . . ?
C2G N1 C12 C1 -178.8(4) . . . . ?
C3 N1 C12 C1 2.2(5) . . . . ?
C2 C1 C12 O1 163.6(5) . . . . ?
C2 C1 C12 N1 -17.1(5) . . . . ?
C17 C2G C13 C14 1.5(6) . . . . ?
N1 C2G C13 C14 -178.8(4) . . . . ?
C2G C13 C14 C15 0.3(7) . . . . ?
C13 C14 C15 C16 -1.3(7) . . . . ?
C14 C15 C16 C17 0.5(7) . . . . ?
C13 C2G C17 C16 -2.3(5) . . . . ?
N1 C2G C17 C16 178.1(3) . . . . ?
C13 C2G C17 C5 177.1(3) . . . . ?
N1 C2G C17 C5 -2.5(4) . . . . ?
C15 C16 C17 C2G 1.2(5) . . . . ?
C15 C16 C17 C5 -178.2(4) . . . . ?
C4 C5 C17 C2G 20.7(4) . . . . ?
C6 C5 C17 C2G -104.9(3) . . . . ?
C4 C5 C17 C16 -159.9(3) . . . . ?
C6 C5 C17 C16 74.5(4) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043

