# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_20181013-cxf_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc21z9x8
_database_code_depnum_ccdc_archive 'CCDC 1905970'
loop_
_audit_author_name
_audit_author_address
'Liang Guo'
;Shihezi University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C23 H22 N3, C2 H6 O'
_chemical_formula_sum            'C25 H28 Cl N3 O'
_chemical_formula_weight         421.95
_chemical_absolute_configuration .
_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 0.0033 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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.347(4)
_cell_length_b                   16.232(3)
_cell_length_c                   7.4296(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2212.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    220
_cell_measurement_theta_max      19.97
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0777 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.8916. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14105
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.463
_diffrn_reflns_theta_min         1.675
_diffrn_ambient_temperature      220
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                3200
_reflns_number_total             4382
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.296
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1050 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.013
_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)+(0.0697P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1398
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C9(H9), C19(H19), C23(H23), C12(H12), C13(H13), C20(H20),
 C7(H7), C22(H22), C6(H6), C8(H8), C21(H21)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.76583(6) 0.80417(6) 0.32096(19) 0.0449(3) Uani 1 1 d . . . . .
N3 N 0.72935(17) 0.54978(19) 0.5374(5) 0.0310(8) Uani 1 1 d . . . . .
N1 N 0.52023(18) 0.39432(19) 0.5401(6) 0.0347(8) Uani 1 1 d . . . . .
N2 N 0.61924(18) 0.59461(19) 0.5043(5) 0.0333(8) Uani 1 1 d . . . . .
O1 O 0.6113(2) 0.8344(3) 0.4720(6) 0.0638(11) Uani 1 1 d . . . . .
H1 H 0.6509 0.8423 0.4209 0.096 Uiso 1 1 calc GR . . . .
C14 C 0.5429(2) 0.4746(2) 0.5253(6) 0.0299(9) Uani 1 1 d . . . . .
C18 C 0.8073(2) 0.5482(2) 0.5529(6) 0.0311(9) Uani 1 1 d . . . . .
C16 C 0.6845(2) 0.4820(2) 0.5520(6) 0.0322(9) Uani 1 1 d . . . . .
H16 H 0.6993 0.4274 0.5735 0.039 Uiso 1 1 calc R . . . .
C11 C 0.4825(2) 0.5261(2) 0.5046(6) 0.0317(9) Uani 1 1 d . . . . .
C15 C 0.6144(2) 0.5087(2) 0.5295(6) 0.0304(9) Uani 1 1 d . . . . .
C5 C 0.4444(2) 0.3937(2) 0.5297(6) 0.0357(10) Uani 1 1 d . . . . .
C10 C 0.4195(2) 0.4749(3) 0.5076(6) 0.0362(10) Uani 1 1 d . . . . .
C1 C 0.5629(2) 0.3202(2) 0.5746(6) 0.0341(10) Uani 1 1 d . . . . .
H1A H 0.5367 0.2861 0.6622 0.041 Uiso 1 1 calc R . . . .
H1B H 0.6093 0.3364 0.6297 0.041 Uiso 1 1 calc R . . . .
C17 C 0.6889(2) 0.6169(2) 0.5099(6) 0.0352(10) Uani 1 1 d . . . . .
H17 H 0.7066 0.6709 0.4967 0.042 Uiso 1 1 calc R . . . .
C9 C 0.3444(2) 0.4910(3) 0.4973(7) 0.0416(11) Uani 1 1 d . . . . .
H9 H 0.3268 0.5450 0.4823 0.050 Uiso 1 1 calc R . . . .
C19 C 0.8395(2) 0.4885(3) 0.6596(7) 0.0399(11) Uani 1 1 d . . . . .
H19 H 0.8107 0.4512 0.7254 0.048 Uiso 1 1 calc R . . . .
C23 C 0.8489(3) 0.6054(3) 0.4609(7) 0.0416(11) Uani 1 1 d . . . . .
H23 H 0.8264 0.6464 0.3910 0.050 Uiso 1 1 calc R . . . .
C12 C 0.4921(2) 0.6126(3) 0.4846(6) 0.0386(11) Uani 1 1 d . . . . .
H12 H 0.4509 0.6466 0.4717 0.046 Uiso 1 1 calc R . . . .
C13 C 0.5583(2) 0.6462(2) 0.4839(7) 0.0388(11) Uani 1 1 d . . . . .
H13 H 0.5642 0.7034 0.4700 0.047 Uiso 1 1 calc R . . . .
C2 C 0.5791(2) 0.2678(3) 0.4092(6) 0.0390(11) Uani 1 1 d . . . . .
H2 H 0.5344 0.2643 0.3353 0.047 Uiso 1 1 calc R . . . .
C20 C 0.9148(3) 0.4847(3) 0.6677(8) 0.0474(12) Uani 1 1 d . . . . .
H20 H 0.9375 0.4437 0.7374 0.057 Uiso 1 1 calc R . . . .
C7 C 0.3232(3) 0.3443(3) 0.5338(8) 0.0512(13) Uani 1 1 d . . . . .
H7 H 0.2896 0.3008 0.5425 0.061 Uiso 1 1 calc R . . . .
C22 C 0.9236(3) 0.6012(3) 0.4735(8) 0.0504(13) Uani 1 1 d . . . . .
H22 H 0.9524 0.6402 0.4125 0.060 Uiso 1 1 calc R . . . .
C6 C 0.3966(2) 0.3273(3) 0.5446(8) 0.0467(12) Uani 1 1 d . . . . .
H6 H 0.4137 0.2732 0.5613 0.056 Uiso 1 1 calc R . . . .
C8 C 0.2971(3) 0.4250(3) 0.5101(8) 0.0502(13) Uani 1 1 d . . . . .
H8 H 0.2466 0.4342 0.5028 0.060 Uiso 1 1 calc R . . . .
C3 C 0.6395(3) 0.3063(3) 0.2952(7) 0.0506(13) Uani 1 1 d . . . . .
H3A H 0.6264 0.3626 0.2653 0.076 Uiso 1 1 calc GR . . . .
H3B H 0.6456 0.2747 0.1854 0.076 Uiso 1 1 calc GR . . . .
H3C H 0.6848 0.3061 0.3626 0.076 Uiso 1 1 calc GR . . . .
C4 C 0.6003(3) 0.1816(3) 0.4677(8) 0.0582(15) Uani 1 1 d . . . . .
H4A H 0.6399 0.1847 0.5540 0.087 Uiso 1 1 calc GR . . . .
H4B H 0.6159 0.1501 0.3637 0.087 Uiso 1 1 calc GR . . . .
H4C H 0.5587 0.1548 0.5230 0.087 Uiso 1 1 calc GR . . . .
C21 C 0.9567(3) 0.5410(3) 0.5736(8) 0.0531(14) Uani 1 1 d . . . . .
H21 H 1.0078 0.5379 0.5784 0.064 Uiso 1 1 calc R . . . .
C25 C 0.6220(4) 0.8340(5) 0.6633(13) 0.095(2) Uani 1 1 d . . . . .
H25A H 0.5748 0.8370 0.7245 0.114 Uiso 1 1 calc R . . . .
H25B H 0.6461 0.7827 0.6996 0.114 Uiso 1 1 calc R . . . .
C24 C 0.6642(5) 0.9001(6) 0.7117(14) 0.131(4) Uani 1 1 d . . . . .
H24A H 0.7128 0.8933 0.6629 0.196 Uiso 1 1 calc GR . . . .
H24B H 0.6668 0.9034 0.8419 0.196 Uiso 1 1 calc GR . . . .
H24C H 0.6427 0.9502 0.6645 0.196 Uiso 1 1 calc GR . . . .


_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
N3 C18 1.434(5) . ?
N3 C16 1.379(5) . ?
N3 C17 1.335(5) . ?
N1 C14 1.372(5) . ?
N1 C5 1.394(5) . ?
N1 C1 1.459(5) . ?
N2 C15 1.410(5) . ?
N2 C17 1.328(5) . ?
N2 C13 1.405(5) . ?
O1 H1 0.8300 . ?
O1 C25 1.435(10) . ?
C14 C11 1.396(5) . ?
C14 C15 1.425(6) . ?
C18 C19 1.384(6) . ?
C18 C23 1.382(6) . ?
C16 H16 0.9400 . ?
C16 C15 1.366(6) . ?
C11 C10 1.424(6) . ?
C11 C12 1.422(6) . ?
C5 C10 1.404(6) . ?
C5 C6 1.394(6) . ?
C10 C9 1.405(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 C2 1.523(6) . ?
C17 H17 0.9400 . ?
C9 H9 0.9400 . ?
C9 C8 1.382(6) . ?
C19 H19 0.9400 . ?
C19 C20 1.384(6) . ?
C23 H23 0.9400 . ?
C23 C22 1.376(7) . ?
C12 H12 0.9400 . ?
C12 C13 1.332(6) . ?
C13 H13 0.9400 . ?
C2 H2 0.9900 . ?
C2 C3 1.528(7) . ?
C2 C4 1.516(6) . ?
C20 H20 0.9400 . ?
C20 C21 1.384(7) . ?
C7 H7 0.9400 . ?
C7 C6 1.377(6) . ?
C7 C8 1.405(7) . ?
C22 H22 0.9400 . ?
C22 C21 1.371(7) . ?
C6 H6 0.9400 . ?
C8 H8 0.9400 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C21 H21 0.9400 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 C24 1.370(10) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?

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
C16 N3 C18 125.1(3) . . ?
C17 N3 C18 125.6(3) . . ?
C17 N3 C16 109.4(3) . . ?
C14 N1 C5 107.7(3) . . ?
C14 N1 C1 129.4(3) . . ?
C5 N1 C1 122.7(3) . . ?
C17 N2 C15 109.0(3) . . ?
C17 N2 C13 127.3(3) . . ?
C13 N2 C15 123.6(3) . . ?
C25 O1 H1 109.5 . . ?
N1 C14 C11 109.7(3) . . ?
N1 C14 C15 130.2(3) . . ?
C11 C14 C15 120.0(3) . . ?
C19 C18 N3 119.0(4) . . ?
C23 C18 N3 119.9(4) . . ?
C23 C18 C19 121.1(4) . . ?
N3 C16 H16 126.3 . . ?
C15 C16 N3 107.4(3) . . ?
C15 C16 H16 126.3 . . ?
C14 C11 C10 107.0(3) . . ?
C14 C11 C12 120.3(4) . . ?
C12 C11 C10 132.7(4) . . ?
N2 C15 C14 116.0(3) . . ?
C16 C15 N2 105.7(3) . . ?
C16 C15 C14 138.2(4) . . ?
N1 C5 C10 108.9(3) . . ?
N1 C5 C6 129.0(4) . . ?
C6 C5 C10 122.1(4) . . ?
C5 C10 C11 106.6(4) . . ?
C5 C10 C9 120.0(4) . . ?
C9 C10 C11 133.4(4) . . ?
N1 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
N1 C1 C2 115.0(4) . . ?
H1A C1 H1B 107.5 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
N3 C17 H17 125.8 . . ?
N2 C17 N3 108.5(3) . . ?
N2 C17 H17 125.8 . . ?
C10 C9 H9 121.1 . . ?
C8 C9 C10 117.9(4) . . ?
C8 C9 H9 121.1 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19 120.6 . . ?
C18 C23 H23 120.5 . . ?
C22 C23 C18 118.9(4) . . ?
C22 C23 H23 120.5 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
N2 C13 H13 120.6 . . ?
C12 C13 N2 118.8(4) . . ?
C12 C13 H13 120.6 . . ?
C1 C2 H2 108.5 . . ?
C1 C2 C3 111.1(4) . . ?
C3 C2 H2 108.5 . . ?
C4 C2 C1 109.5(4) . . ?
C4 C2 H2 108.5 . . ?
C4 C2 C3 110.5(4) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 121.9(4) . . ?
C8 C7 H7 119.0 . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C5 C6 H6 121.5 . . ?
C7 C6 C5 117.0(4) . . ?
C7 C6 H6 121.5 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.9(5) . . ?
C22 C21 H21 120.0 . . ?
O1 C25 H25A 109.8 . . ?
O1 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
C24 C25 O1 109.5(8) . . ?
C24 C25 H25A 109.8 . . ?
C24 C25 H25B 109.8 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
