# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1114dxwczq01_0m
_database_code_depnum_ccdc_archive 'CCDC 2045491'
loop_
_audit_author_name
_audit_author_address
'Xiaowei Dou'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-11-13
_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         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32
_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                   8.9919(2)
_cell_length_b                   12.2777(2)
_cell_length_c                   14.0831(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1554.77(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9167
_cell_measurement_temperature    153
_cell_measurement_theta_max      74.501
_cell_measurement_theta_min      3.138
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1627 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.8396. 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    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13884
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_min         5.838
_diffrn_ambient_temperature      153.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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         0.722
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2928
_reflns_number_total             3127
_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         -0.178
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.087
_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)+(0.0418P)²+0.1745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C4(H4), C3(H3), C11(H11), C9(H9), C1(H1), C10(H10), C2(H2)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 N1(H1A)
;
_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 0.44330(15) 0.33006(10) 0.62936(10) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.04153(16) 0.37473(11) 0.48498(11) 0.0334(3) Uani 1 1 d . . . . .
O3 O 0.03980(15) 0.54895(11) 0.53354(11) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.27399(19) 0.25244(13) 0.53756(13) 0.0269(4) Uani 1 1 d . . . . .
H1A H 0.348056 0.210848 0.535031 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.3108(2) 0.34368(14) 0.58391(13) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.18709(19) 0.54565(16) 0.73811(13) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.2819(2) 0.53324(14) 0.64907(13) 0.0228(4) Uani 1 1 d . . . . .
H7 H 0.271129 0.601397 0.610805 0.027 Uiso 1 1 calc R . . . .
C15 C 0.2316(2) 0.43902(14) 0.58810(13) 0.0222(4) Uani 1 1 d . . . . .
C16 C 0.0992(2) 0.44788(14) 0.53173(14) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.1144(2) 0.64364(17) 0.75673(16) 0.0300(4) Uani 1 1 d . . . . .
H5 H 0.124355 0.702778 0.713691 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5164(2) 0.42202(15) 0.66358(13) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.4449(2) 0.52060(15) 0.67442(13) 0.0242(4) Uani 1 1 d . . . . .
C12 C 0.6652(2) 0.40717(18) 0.68554(15) 0.0308(4) Uani 1 1 d . . . . .
H12 H 0.710972 0.338160 0.676841 0.037 Uiso 1 1 calc R . . . .
C4 C 0.0279(2) 0.65556(18) 0.83736(16) 0.0356(5) Uani 1 1 d . . . . .
H4 H -0.020454 0.722905 0.849659 0.043 Uiso 1 1 calc R . . . .
C3 C 0.0117(2) 0.5704(2) 0.89954(15) 0.0380(5) Uani 1 1 d . . . . .
H3 H -0.048922 0.578475 0.954338 0.046 Uiso 1 1 calc R . . . .
C11 C 0.7463(2) 0.4945(2) 0.72039(17) 0.0370(5) Uani 1 1 d . . . . .
H11 H 0.848764 0.486006 0.735057 0.044 Uiso 1 1 calc R . . . .
C9 C 0.5281(2) 0.60686(17) 0.71072(16) 0.0324(4) Uani 1 1 d . . . . .
H9 H 0.481801 0.675617 0.719871 0.039 Uiso 1 1 calc R . . . .
C1 C 0.1715(2) 0.46048(18) 0.80161(15) 0.0332(5) Uani 1 1 d . . . . .
H1 H 0.220879 0.393395 0.789991 0.040 Uiso 1 1 calc R . . . .
C10 C 0.6771(2) 0.59432(19) 0.73374(17) 0.0375(5) Uani 1 1 d . . . . .
H10 H 0.731702 0.654072 0.758639 0.045 Uiso 1 1 calc R . . . .
C2 C 0.0838(2) 0.4724(2) 0.88243(16) 0.0393(5) Uani 1 1 d . . . . .
H2 H 0.073398 0.413582 0.925765 0.047 Uiso 1 1 calc R . . . .
C17 C -0.0931(3) 0.56363(19) 0.4774(2) 0.0464(6) Uani 1 1 d . . . . .
H17A H -0.173281 0.515204 0.500632 0.056 Uiso 1 1 calc R . . . .
H17B H -0.073047 0.545877 0.410010 0.056 Uiso 1 1 calc R . . . .
C18 C -0.1388(3) 0.6806(2) 0.4869(2) 0.0604(8) Uani 1 1 d . . . . .
H18A H -0.230005 0.693164 0.450370 0.091 Uiso 1 1 calc GR . . . .
H18B H -0.059412 0.727599 0.462526 0.091 Uiso 1 1 calc GR . . . .
H18C H -0.156868 0.697428 0.553900 0.091 Uiso 1 1 calc GR . . . .
H1B H 0.195(3) 0.253(2) 0.503(2) 0.044(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 C14 1.363(2) . ?
O1 C13 1.392(2) . ?
O2 C16 1.228(2) . ?
O3 C16 1.351(2) . ?
O3 C17 1.445(3) . ?
N1 H1A 0.8400 . ?
N1 C14 1.338(2) . ?
N1 H1B 0.86(3) . ?
C14 C15 1.372(2) . ?
C6 C7 1.524(3) . ?
C6 C5 1.394(3) . ?
C6 C1 1.383(3) . ?
C7 H7 1.0000 . ?
C7 C15 1.510(2) . ?
C7 C8 1.517(2) . ?
C15 C16 1.435(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(3) . ?
C13 C8 1.379(3) . ?
C13 C12 1.385(3) . ?
C8 C9 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.372(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(3) . ?
C10 H10 0.9500 . ?
C2 H2 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.500(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C14 O1 C13 118.41(14) . . ?
C16 O3 C17 115.54(15) . . ?
H1A N1 H1B 129.5 . . ?
C14 N1 H1A 109.5 . . ?
C14 N1 H1B 118.1(18) . . ?
O1 C14 C15 122.58(16) . . ?
N1 C14 O1 110.05(16) . . ?
N1 C14 C15 127.37(17) . . ?
C5 C6 C7 120.22(18) . . ?
C1 C6 C7 120.88(17) . . ?
C1 C6 C5 118.90(18) . . ?
C6 C7 H7 107.8 . . ?
C15 C7 C6 112.16(14) . . ?
C15 C7 H7 107.8 . . ?
C15 C7 C8 110.17(15) . . ?
C8 C7 C6 110.92(15) . . ?
C8 C7 H7 107.8 . . ?
C14 C15 C7 121.53(16) . . ?
C14 C15 C16 118.15(16) . . ?
C16 C15 C7 120.32(15) . . ?
O2 C16 O3 121.00(17) . . ?
O2 C16 C15 126.24(17) . . ?
O3 C16 C15 112.76(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C8 C13 O1 122.00(16) . . ?
C8 C13 C12 122.76(18) . . ?
C12 C13 O1 115.24(17) . . ?
C13 C8 C7 120.95(16) . . ?
C13 C8 C9 117.23(17) . . ?
C9 C8 C7 121.82(17) . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.67(19) . . ?
C10 C11 H11 120.2 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.3 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O3 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
O3 C17 C18 107.3(2) . . ?
H17A C17 H17B 108.5 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
