# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
# 
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data_takeda_kpnx38_autored
_database_code_depnum_ccdc_archive 'CCDC 2256541'
loop_
_audit_author_name
_audit_author_address
'Norihiko Takeda'
;Kobe Pharmaceutical University
Japan
;
_audit_update_record             
;
2023-04-15 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 Cl N O3'
_chemical_formula_sum            'C19 H18 Cl N O3'
_chemical_formula_weight         343.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H18ClNO3
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   11.0033(4)
_cell_length_b                   15.9828(5)
_cell_length_c                   19.3880(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3409.64(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    27242
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.8060
_cell_measurement_theta_min      2.1660
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            64718
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.101
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00  90.00  360
  3  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00 180.00  360
  4  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       .
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0386158000
_diffrn_orient_matrix_UB_12      -0.0347386000
_diffrn_orient_matrix_UB_13      0.0062321000
_diffrn_orient_matrix_UB_21      -0.0334785000
_diffrn_orient_matrix_UB_22      -0.0096707000
_diffrn_orient_matrix_UB_23      0.0302361000
_diffrn_orient_matrix_UB_31      -0.0392952000
_diffrn_orient_matrix_UB_32      -0.0258485000
_diffrn_orient_matrix_UB_33      -0.0196389000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3294
_reflns_number_total             4123
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+2.3013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19)
1.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.32768(5) 1.16469(3) 0.62201(2) 0.03317(13) Uani 1 1 d . . . . .
O1 O 0.40652(10) 0.57193(6) 0.39908(5) 0.0162(2) Uani 1 1 d . . . . .
O2 O 0.40156(10) 0.62903(7) 0.26309(6) 0.0196(3) Uani 1 1 d . . . . .
O3 O 0.20708(10) 0.58557(7) 0.25680(6) 0.0176(2) Uani 1 1 d . . . . .
N1 N 0.36589(12) 0.65365(8) 0.41737(7) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.35931(15) 0.44982(9) 0.33538(8) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.27385(15) 0.38631(10) 0.33362(8) 0.0182(3) Uani 1 1 d . . . . .
H2 H 0.191003 0.398584 0.343003 0.022 Uiso 1 1 calc R U . . .
C3 C 0.30821(16) 0.30468(10) 0.31824(8) 0.0219(4) Uani 1 1 d . . . . .
H3 H 0.249177 0.261308 0.317652 0.026 Uiso 1 1 calc R U . . .
C4 C 0.42823(16) 0.28684(10) 0.30383(8) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.451874 0.231176 0.293080 0.026 Uiso 1 1 calc R U . . .
C5 C 0.51415(16) 0.35002(10) 0.30503(8) 0.0211(4) Uani 1 1 d . . . . .
H5 H 0.596810 0.337623 0.295241 0.025 Uiso 1 1 calc R U . . .
C6 C 0.47984(15) 0.43169(10) 0.32053(8) 0.0189(3) Uani 1 1 d . . . . .
H6 H 0.538934 0.475026 0.320957 0.023 Uiso 1 1 calc R U . . .
C7 C 0.32002(14) 0.53844(9) 0.35185(8) 0.0144(3) Uani 1 1 d . . . . .
H7 H 0.237614 0.537831 0.373589 0.017 Uiso 1 1 calc R U . . .
C8 C 0.31701(14) 0.59064(9) 0.28595(8) 0.0132(3) Uani 1 1 d . . . . .
C9 C 0.19425(15) 0.62655(10) 0.19037(8) 0.0195(3) Uani 1 1 d . . . . .
H9A H 0.232869 0.592318 0.154623 0.029 Uiso 1 1 calc R U . . .
H9B H 0.233422 0.681583 0.192014 0.029 Uiso 1 1 calc R U . . .
H9C H 0.107788 0.633422 0.179640 0.029 Uiso 1 1 calc R U . . .
C10 C 0.43694(14) 0.68733(9) 0.46221(8) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.54809(16) 0.64699(11) 0.49180(9) 0.0248(4) Uani 1 1 d . . . . .
H11A H 0.551139 0.588186 0.477590 0.037 Uiso 1 1 calc R U . . .
H11B H 0.545269 0.650299 0.542245 0.037 Uiso 1 1 calc R U . . .
H11C H 0.620641 0.676082 0.474927 0.037 Uiso 1 1 calc R U . . .
C12 C 0.40014(14) 0.77154(9) 0.48297(8) 0.0165(3) Uani 1 1 d . . . . .
H12 H 0.330393 0.794764 0.461351 0.020 Uiso 1 1 calc R U . . .
C13 C 0.45714(14) 0.81830(10) 0.53004(8) 0.0165(3) Uani 1 1 d . . . . .
H13 H 0.526219 0.794355 0.551818 0.020 Uiso 1 1 calc R U . . .
C14 C 0.42292(14) 0.90324(9) 0.55120(8) 0.0149(3) Uani 1 1 d . . . . .
C15 C 0.33911(15) 0.95187(10) 0.51504(8) 0.0174(3) Uani 1 1 d . . . . .
H15 H 0.302051 0.929756 0.474707 0.021 Uiso 1 1 calc R U . . .
C16 C 0.30887(16) 1.03169(10) 0.53675(8) 0.0205(3) Uani 1 1 d . . . . .
H16 H 0.251581 1.064153 0.511703 0.025 Uiso 1 1 calc R U . . .
C17 C 0.36340(16) 1.06353(10) 0.59558(8) 0.0206(4) Uani 1 1 d . . . . .
C18 C 0.44582(15) 1.01708(10) 0.63315(8) 0.0207(4) Uani 1 1 d . . . . .
H18 H 0.481662 1.039284 0.673798 0.025 Uiso 1 1 calc R U . . .
C19 C 0.47530(14) 0.93742(10) 0.61043(8) 0.0181(3) Uani 1 1 d . . . . .
H19 H 0.532549 0.905272 0.635784 0.022 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 C17 1.7410(16) . ?
O1 N1 1.4252(16) . ?
O1 C7 1.4251(18) . ?
O2 C8 1.1993(18) . ?
O3 C8 1.3375(18) . ?
O3 C9 1.4518(18) . ?
N1 C10 1.287(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.388(2) . ?
C1 C7 1.515(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.526(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.497(2) . ?
C10 C12 1.462(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.336(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.467(2) . ?
C14 C15 1.395(2) . ?
C14 C19 1.396(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 C18 1.380(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C19 H19 0.9500 . ?

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 O1 N1 107.13(11) . . ?
C8 O3 C9 115.81(12) . . ?
C10 N1 O1 111.15(12) . . ?
C2 C1 C6 119.41(14) . . ?
C2 C1 C7 119.80(14) . . ?
C6 C1 C7 120.78(14) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.57(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.84(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.99(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.19(16) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.99(15) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C1 107.22(12) . . ?
O1 C7 H7 109.8 . . ?
O1 C7 C8 110.31(12) . . ?
C1 C7 H7 109.8 . . ?
C1 C7 C8 109.93(12) . . ?
C8 C7 H7 109.8 . . ?
O2 C8 O3 125.20(14) . . ?
O2 C8 C7 124.90(14) . . ?
O3 C8 C7 109.89(12) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 125.10(14) . . ?
N1 C10 C12 113.75(14) . . ?
C12 C10 C11 121.15(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12 117.5 . . ?
C13 C12 C10 124.96(15) . . ?
C13 C12 H12 117.5 . . ?
C12 C13 H13 117.0 . . ?
C12 C13 C14 126.02(15) . . ?
C14 C13 H13 117.0 . . ?
C15 C14 C13 123.00(14) . . ?
C15 C14 C19 117.92(14) . . ?
C19 C14 C13 119.08(14) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.31(15) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.01(16) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 Cl1 119.06(14) . . ?
C18 C17 Cl1 119.51(13) . . ?
C18 C17 C16 121.43(15) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.71(15) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.63(15) . . ?
C18 C19 H19 119.2 . . ?

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
Cl1 C17 C18 C19 -178.50(12) . . . . ?
O1 N1 C10 C11 0.1(2) . . . . ?
O1 N1 C10 C12 179.85(12) . . . . ?
O1 C7 C8 O2 29.2(2) . . . . ?
O1 C7 C8 O3 -152.21(12) . . . . ?
N1 O1 C7 C1 -176.95(11) . . . . ?
N1 O1 C7 C8 63.37(14) . . . . ?
N1 C10 C12 C13 178.09(15) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C7 C8 O2 -88.82(18) . . . . ?
C1 C7 C8 O3 89.76(15) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C7 O1 136.16(14) . . . . ?
C2 C1 C7 C8 -103.91(16) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C6 C1 C7 O1 -45.22(18) . . . . ?
C6 C1 C7 C8 74.71(18) . . . . ?
C7 O1 N1 C10 177.54(12) . . . . ?
C7 C1 C2 C3 179.67(14) . . . . ?
C7 C1 C6 C5 -179.54(14) . . . . ?
C9 O3 C8 O2 3.6(2) . . . . ?
C9 O3 C8 C7 -174.92(12) . . . . ?
C10 C12 C13 C14 179.26(14) . . . . ?
C11 C10 C12 C13 -2.1(2) . . . . ?
C12 C13 C14 C15 -12.5(2) . . . . ?
C12 C13 C14 C19 166.99(15) . . . . ?
C13 C14 C15 C16 179.80(15) . . . . ?
C13 C14 C19 C18 -179.55(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C15 C16 C17 Cl1 178.76(12) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 C14 -0.6(2) . . . . ?
C19 C14 C15 C16 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.870
