# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_wch262_0m
_database_code_depnum_ccdc_archive 'CCDC 2260854'
loop_
_audit_author_name
_audit_author_address
'Xiaowei Dou'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2023-05-05 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;
_audit_creation_date             2022-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N O'
_chemical_formula_sum            'C19 H17 N O'
_chemical_formula_weight         275.33
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.1061(2)
_cell_length_b                   12.0634(2)
_cell_length_c                   14.0083(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1538.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.572
_cell_measurement_theta_min      4.838
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1149 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.9139. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14446
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.546
_diffrn_reflns_theta_min         4.838
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2975
_reflns_number_total             3105
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+0.2192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C19(H19), C2(H2), C3(H3), C15(H15), C18(H18),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.05526(16) 0.72177(11) 0.19672(11) 0.0493(4) Uani 1 1 d . . . . .
N1 N 0.19921(17) 0.35952(12) 0.31302(12) 0.0347(3) Uani 1 1 d . . . . .
H1 H 0.136771 0.304262 0.307176 0.042 Uiso 1 1 calc R . . . .
C1 C 0.33736(19) 0.35405(14) 0.35332(13) 0.0313(4) Uani 1 1 d . . . . .
C11 C 0.17686(19) 0.46704(14) 0.28364(12) 0.0311(4) Uani 1 1 d . . . . .
C14 C -0.0593(2) 0.57737(15) 0.40319(13) 0.0346(4) Uani 1 1 d . . . . .
C6 C 0.40342(19) 0.46070(14) 0.34710(12) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.29671(19) 0.53022(14) 0.30233(12) 0.0303(4) Uani 1 1 d . . . . .
C13 C -0.08776(19) 0.53081(16) 0.30499(13) 0.0369(4) Uani 1 1 d . . . . .
H13A H -0.163574 0.576697 0.273301 0.044 Uiso 1 1 calc R . . . .
H13B H -0.127850 0.454934 0.311741 0.044 Uiso 1 1 calc R . . . .
C9 C 0.1181(2) 0.64354(15) 0.23180(13) 0.0355(4) Uani 1 1 d . . . . .
C4 C 0.6171(2) 0.38554(17) 0.42323(14) 0.0399(4) Uani 1 1 d . . . . .
H4 H 0.713939 0.394752 0.447189 0.048 Uiso 1 1 calc R . . . .
C10 C 0.0496(2) 0.52613(15) 0.24004(13) 0.0337(4) Uani 1 1 d . . . . .
C5 C 0.5462(2) 0.47459(16) 0.38247(13) 0.0358(4) Uani 1 1 d . . . . .
H5 H 0.593454 0.544624 0.378388 0.043 Uiso 1 1 calc R . . . .
C19 C -0.0904(3) 0.68678(17) 0.42470(15) 0.0495(6) Uani 1 1 d . . . . .
H19 H -0.134680 0.732689 0.377725 0.059 Uiso 1 1 calc R . . . .
C2 C 0.4092(2) 0.26438(15) 0.39528(14) 0.0383(4) Uani 1 1 d . . . . .
H2 H 0.363454 0.193804 0.399832 0.046 Uiso 1 1 calc R . . . .
C8 C 0.2718(2) 0.64850(15) 0.27391(16) 0.0374(4) Uani 1 1 d . . . . .
C3 C 0.5492(2) 0.28181(17) 0.43000(13) 0.0406(4) Uani 1 1 d . . . . .
H3 H 0.600549 0.222127 0.459077 0.049 Uiso 1 1 calc R . . . .
C12 C 0.0056(3) 0.4838(2) 0.14108(15) 0.0491(5) Uani 1 1 d . . . . .
H12A H 0.093067 0.478133 0.100648 0.074 Uiso 1 1 calc GR . . . .
H12B H -0.064425 0.535486 0.112078 0.074 Uiso 1 1 calc GR . . . .
H12C H -0.040176 0.410573 0.147168 0.074 Uiso 1 1 calc GR . . . .
C15 C 0.0023(3) 0.51163(18) 0.47396(15) 0.0480(5) Uani 1 1 d . . . . .
H15 H 0.023202 0.435954 0.461021 0.058 Uiso 1 1 calc R . . . .
C18 C -0.0579(4) 0.7305(2) 0.51365(17) 0.0661(8) Uani 1 1 d . . . . .
H18 H -0.078901 0.806029 0.526991 0.079 Uiso 1 1 calc R . . . .
C16 C 0.0338(3) 0.5550(2) 0.56323(16) 0.0591(6) Uani 1 1 d . . . . .
H16 H 0.075470 0.508924 0.611102 0.071 Uiso 1 1 calc R . . . .
C17 C 0.0048(3) 0.6647(2) 0.58269(16) 0.0617(7) Uani 1 1 d . . . . .
H17 H 0.027973 0.694809 0.643517 0.074 Uiso 1 1 calc R . . . .
H8A H 0.272(3) 0.7017(18) 0.3303(18) 0.049(6) Uiso 1 1 d . . . . .
H8B H 0.342(3) 0.6775(19) 0.2242(19) 0.056(7) Uiso 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
O1 C9 1.208(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.380(2) . ?
N1 C11 1.376(2) . ?
C1 C6 1.423(2) . ?
C1 C2 1.394(2) . ?
C11 C7 1.357(2) . ?
C11 C10 1.491(2) . ?
C14 C13 1.508(3) . ?
C14 C19 1.383(3) . ?
C14 C15 1.388(3) . ?
C6 C7 1.429(2) . ?
C6 C5 1.401(3) . ?
C7 C8 1.499(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C10 1.548(3) . ?
C9 C10 1.552(3) . ?
C9 C8 1.520(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(3) . ?
C4 C3 1.399(3) . ?
C10 C12 1.531(3) . ?
C5 H5 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C8 H8A 1.02(2) . ?
C8 H8B 1.01(3) . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.375(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(4) . ?
C17 H17 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
C1 N1 H1 126.2 . . ?
C11 N1 H1 126.2 . . ?
C11 N1 C1 107.59(14) . . ?
N1 C1 C6 108.48(15) . . ?
N1 C1 C2 129.58(17) . . ?
C2 C1 C6 121.94(17) . . ?
N1 C11 C10 133.48(16) . . ?
C7 C11 N1 110.66(15) . . ?
C7 C11 C10 115.82(15) . . ?
C19 C14 C13 121.26(17) . . ?
C19 C14 C15 118.18(19) . . ?
C15 C14 C13 120.54(17) . . ?
C1 C6 C7 105.67(15) . . ?
C5 C6 C1 118.60(16) . . ?
C5 C6 C7 135.73(17) . . ?
C11 C7 C6 107.58(15) . . ?
C11 C7 C8 111.22(16) . . ?
C6 C7 C8 141.12(17) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C14 C13 C10 114.26(14) . . ?
H13A C13 H13B 107.6 . . ?
C10 C13 H13A 108.7 . . ?
C10 C13 H13B 108.7 . . ?
O1 C9 C10 123.57(18) . . ?
O1 C9 C8 124.28(18) . . ?
C8 C9 C10 112.15(15) . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.23(18) . . ?
C3 C4 H4 119.4 . . ?
C11 C10 C13 113.87(14) . . ?
C11 C10 C9 98.89(14) . . ?
C11 C10 C12 114.52(16) . . ?
C13 C10 C9 109.58(15) . . ?
C12 C10 C13 109.42(16) . . ?
C12 C10 C9 110.04(16) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.24(18) . . ?
C4 C5 H5 120.4 . . ?
C14 C19 H19 119.5 . . ?
C14 C19 C18 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.63(18) . . ?
C3 C2 H2 121.2 . . ?
C7 C8 C9 101.83(15) . . ?
C7 C8 H8A 113.2(13) . . ?
C7 C8 H8B 114.6(14) . . ?
C9 C8 H8A 109.1(14) . . ?
C9 C8 H8B 109.4(14) . . ?
H8A C8 H8B 108.4(19) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.35(18) . . ?
C2 C3 H3 119.3 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
