# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_md_zxjw1
_database_code_depnum_ccdc_archive 'CCDC 2306712'
loop_
_audit_author_name
_audit_author_address
'ZHAO xiaojing'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            md_zxjw1
_chemical_formula_moiety         'C22 H17 F2 N O'
_chemical_formula_sum            'C22 H17 F2 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         349.36
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5585(4)
_cell_length_b                   7.8842(3)
_cell_length_c                   11.8135(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.2350(10)
_cell_angle_gamma                90
_cell_volume                     850.30(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.9178
_cell_measurement_theta_max      68.3620
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364

_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            17617
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         68.48
_diffrn_reflns_theta_full        68.48
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3037
_reflns_number_gt                2967
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0958
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_number_reflns         3037
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.1827P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.55075(15) 0.5551(2) 0.47191(12) 0.0329(4) Uani d . . . 1 . .
O O1 0.75920(18) 0.3462(3) 0.87892(15) 0.0328(4) Uani d . . . 1 . .
F F2 0.76970(17) 0.6539(2) 0.49739(12) 0.0354(4) Uani d . . . 1 . .
N N1 0.8488(2) 0.3473(3) 0.67170(17) 0.0282(5) Uani d . . . 1 . .
H H4 0.91787 0.324307 0.737904 0.034 Uiso calc U . R 1 . .
C C1 0.7737(3) 0.1561(4) 0.3310(2) 0.0396(7) Uani d . . . 1 . .
H H1 0.756923 0.117607 0.251916 0.048 Uiso calc U . R 1 . .
C C2 0.7134(3) 0.3081(4) 0.3527(2) 0.0330(6) Uani d . . . 1 . .
H H6 0.65538 0.375566 0.289496 0.04 Uiso calc U . R 1 . .
C C3 0.7404(3) 0.3586(4) 0.4697(2) 0.0285(5) Uani d . . . 1 . .
C C4 0.6961(3) 0.5142(3) 0.5202(2) 0.0268(5) Uani d . . . 1 . .
C C5 0.7362(2) 0.4809(3) 0.6570(2) 0.0260(5) Uani d . . . 1 . .
C C6 0.5999(3) 0.4079(3) 0.6857(2) 0.0259(5) Uani d . . . 1 . .
H H13 0.522779 0.496011 0.670173 0.031 Uiso calc U . R 1 . .
H H12 0.561245 0.310973 0.632371 0.031 Uiso calc U . R 1 . .
C C7 0.6339(3) 0.3490(3) 0.8136(2) 0.0265(5) Uani d . . . 1 . .
C C8 0.5104(3) 0.2935(3) 0.8575(2) 0.0285(5) Uani d . . . 1 . .
C C9 0.5378(3) 0.2666(4) 0.9793(2) 0.0372(6) Uani d . . . 1 . .
H H16 0.633771 0.283474 1.03121 0.045 Uiso calc U . R 1 . .
C C10 0.4281(4) 0.2164(4) 1.0246(3) 0.0442(7) Uani d . . . 1 . .
H H15 0.448272 0.199035 1.10747 0.053 Uiso calc U . R 1 . .
C C11 0.2868(4) 0.1907(4) 0.9492(3) 0.0449(7) Uani d . . . 1 . .
H H2 0.210364 0.156634 0.980464 0.054 Uiso calc U . R 1 . .
C C12 0.8589(3) 0.0599(4) 0.4251(3) 0.0401(6) Uani d . . . 1 . .
H H3 0.898907 -0.044191 0.40848 0.048 Uiso calc U . R 1 . .
C C13 0.8874(3) 0.1103(4) 0.5421(3) 0.0354(6) Uani d . . . 1 . .
H H5 0.945359 0.042591 0.605263 0.042 Uiso calc U . R 1 . .
C C14 0.8282(3) 0.2635(4) 0.5637(2) 0.0285(5) Uani d . . . 1 . .
C C15 0.7912(3) 0.6408(4) 0.7272(2) 0.0265(5) Uani d . . . 1 . .
C C16 0.9317(3) 0.6556(4) 0.8052(2) 0.0323(6) Uani d . . . 1 . .
H H11 0.997793 0.562914 0.815629 0.039 Uiso calc U . R 1 . .
C C17 0.9760(3) 0.8045(4) 0.8679(2) 0.0384(7) Uani d . . . 1 . .
H H7 1.072778 0.813605 0.920023 0.046 Uiso calc U . R 1 . .
C C18 0.8807(3) 0.9402(4) 0.8552(3) 0.0396(7) Uani d . . . 1 . .
H H10 0.910629 1.040738 0.900251 0.047 Uiso calc U . R 1 . .
C C19 0.7415(3) 0.9280(4) 0.7763(3) 0.0375(6) Uani d . . . 1 . .
H H8 0.67624 1.021605 0.765387 0.045 Uiso calc U . R 1 . .
C C20 0.6968(3) 0.7788(4) 0.7129(2) 0.0315(6) Uani d . . . 1 . .
H H9 0.600822 0.77118 0.659257 0.038 Uiso calc U . R 1 . .
C C21 0.3692(3) 0.2671(4) 0.7823(2) 0.0342(6) Uani d . . . 1 . .
H H14 0.348844 0.284628 0.69946 0.041 Uiso calc U . R 1 . .
C C22 0.2589(3) 0.2154(4) 0.8282(3) 0.0438(7) Uani d . . . 1 . .
H H17 0.163071 0.196621 0.776398 0.053 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.375(3) ?
O1 C7 . 1.218(3) ?
F2 C4 . 1.376(3) ?
N1 C14 . 1.398(3) ?
N1 C5 . 1.479(3) ?
N1 H4 . 0.88 ?
C1 C2 . 1.387(5) ?
C1 C12 . 1.392(5) ?
C1 H1 . 0.95 ?
C2 C3 . 1.386(4) ?
C2 H6 . 0.95 ?
C3 C14 . 1.396(4) ?
C3 C4 . 1.480(4) ?
C4 C5 . 1.569(3) ?
C5 C15 . 1.515(4) ?
C5 C6 . 1.550(3) ?
C6 C7 . 1.521(3) ?
C6 H13 . 0.99 ?
C6 H12 . 0.99 ?
C7 C8 . 1.489(3) ?
C8 C21 . 1.394(3) ?
C8 C9 . 1.400(4) ?
C9 C10 . 1.369(4) ?
C9 H16 . 0.95 ?
C10 C11 . 1.394(5) ?
C10 H15 . 0.95 ?
C11 C22 . 1.389(5) ?
C11 H2 . 0.95 ?
C12 C13 . 1.386(4) ?
C12 H3 . 0.95 ?
C13 C14 . 1.389(4) ?
C13 H5 . 0.95 ?
C15 C16 . 1.390(3) ?
C15 C20 . 1.391(4) ?
C16 C17 . 1.386(4) ?
C16 H11 . 0.95 ?
C17 C18 . 1.384(5) ?
C17 H7 . 0.95 ?
C18 C19 . 1.384(4) ?
C18 H10 . 0.95 ?
C19 C20 . 1.392(4) ?
C19 H8 . 0.95 ?
C20 H9 . 0.95 ?
C21 C22 . 1.382(4) ?
C21 H14 . 0.95 ?
C22 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 N1 C5 . . 109.21(19) ?
C14 N1 H4 . . 125.4 ?
C5 N1 H4 . . 125.4 ?
C2 C1 C12 . . 120.0(2) ?
C2 C1 H1 . . 120.0 ?
C12 C1 H1 . . 120.0 ?
C3 C2 C1 . . 117.9(3) ?
C3 C2 H6 . . 121.1 ?
C1 C2 H6 . . 121.1 ?
C2 C3 C14 . . 122.0(3) ?
C2 C3 C4 . . 130.5(2) ?
C14 C3 C4 . . 107.5(2) ?
F1 C4 F2 . . 104.08(19) ?
F1 C4 C3 . . 113.7(2) ?
F2 C4 C3 . . 111.16(19) ?
F1 C4 C5 . . 112.01(18) ?
F2 C4 C5 . . 110.66(19) ?
C3 C4 C5 . . 105.4(2) ?
N1 C5 C15 . . 113.96(19) ?
N1 C5 C6 . . 109.9(2) ?
C15 C5 C6 . . 111.52(19) ?
N1 C5 C4 . . 100.76(18) ?
C15 C5 C4 . . 111.3(2) ?
C6 C5 C4 . . 108.85(18) ?
C7 C6 C5 . . 112.63(18) ?
C7 C6 H13 . . 109.1 ?
C5 C6 H13 . . 109.1 ?
C7 C6 H12 . . 109.1 ?
C5 C6 H12 . . 109.1 ?
H13 C6 H12 . . 107.8 ?
O1 C7 C8 . . 120.4(2) ?
O1 C7 C6 . . 121.0(2) ?
C8 C7 C6 . . 118.6(2) ?
C21 C8 C9 . . 118.9(2) ?
C21 C8 C7 . . 122.7(2) ?
C9 C8 C7 . . 118.5(2) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H16 . . 119.5 ?
C8 C9 H16 . . 119.5 ?
C9 C10 C11 . . 120.1(3) ?
C9 C10 H15 . . 120.0 ?
C11 C10 H15 . . 120.0 ?
C22 C11 C10 . . 119.5(3) ?
C22 C11 H2 . . 120.3 ?
C10 C11 H2 . . 120.3 ?
C13 C12 C1 . . 122.4(3) ?
C13 C12 H3 . . 118.8 ?
C1 C12 H3 . . 118.8 ?
C12 C13 C14 . . 117.5(3) ?
C12 C13 H5 . . 121.2 ?
C14 C13 H5 . . 121.2 ?
C13 C14 C3 . . 120.2(2) ?
C13 C14 N1 . . 128.6(2) ?
C3 C14 N1 . . 111.2(2) ?
C16 C15 C20 . . 118.6(2) ?
C16 C15 C5 . . 122.9(2) ?
C20 C15 C5 . . 118.5(2) ?
C17 C16 C15 . . 120.5(3) ?
C17 C16 H11 . . 119.8 ?
C15 C16 H11 . . 119.8 ?
C18 C17 C16 . . 120.7(2) ?
C18 C17 H7 . . 119.7 ?
C16 C17 H7 . . 119.7 ?
C19 C18 C17 . . 119.3(3) ?
C19 C18 H10 . . 120.3 ?
C17 C18 H10 . . 120.3 ?
C18 C19 C20 . . 120.1(3) ?
C18 C19 H8 . . 119.9 ?
C20 C19 H8 . . 119.9 ?
C15 C20 C19 . . 120.7(2) ?
C15 C20 H9 . . 119.6 ?
C19 C20 H9 . . 119.6 ?
C22 C21 C8 . . 120.1(3) ?
C22 C21 H14 . . 119.9 ?
C8 C21 H14 . . 119.9 ?
C21 C22 C11 . . 120.6(3) ?
C21 C22 H17 . . 119.7 ?
C11 C22 H17 . . 119.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C1 C2 C3 . . . . -0.3(4) ?
C1 C2 C3 C14 . . . . 1.6(4) ?
C1 C2 C3 C4 . . . . 177.7(3) ?
C2 C3 C4 F1 . . . . 47.2(4) ?
C14 C3 C4 F1 . . . . -136.2(2) ?
C2 C3 C4 F2 . . . . -69.8(3) ?
C14 C3 C4 F2 . . . . 106.7(2) ?
C2 C3 C4 C5 . . . . 170.2(2) ?
C14 C3 C4 C5 . . . . -13.2(3) ?
C14 N1 C5 C15 . . . . -143.3(2) ?
C14 N1 C5 C6 . . . . 90.8(2) ?
C14 N1 C5 C4 . . . . -24.0(2) ?
F1 C4 C5 N1 . . . . 146.2(2) ?
F2 C4 C5 N1 . . . . -98.2(2) ?
C3 C4 C5 N1 . . . . 22.1(2) ?
F1 C4 C5 C15 . . . . -92.6(2) ?
F2 C4 C5 C15 . . . . 23.0(3) ?
C3 C4 C5 C15 . . . . 143.3(2) ?
F1 C4 C5 C6 . . . . 30.7(3) ?
F2 C4 C5 C6 . . . . 146.3(2) ?
C3 C4 C5 C6 . . . . -93.4(2) ?
N1 C5 C6 C7 . . . . 62.7(3) ?
C15 C5 C6 C7 . . . . -64.6(3) ?
C4 C5 C6 C7 . . . . 172.2(2) ?
C5 C6 C7 O1 . . . . -7.0(3) ?
C5 C6 C7 C8 . . . . 173.4(2) ?
O1 C7 C8 C21 . . . . -168.9(3) ?
C6 C7 C8 C21 . . . . 10.6(4) ?
O1 C7 C8 C9 . . . . 10.9(4) ?
C6 C7 C8 C9 . . . . -169.5(2) ?
C21 C8 C9 C10 . . . . -0.5(4) ?
C7 C8 C9 C10 . . . . 179.6(3) ?
C8 C9 C10 C11 . . . . 0.2(5) ?
C9 C10 C11 C22 . . . . 0.4(5) ?
C2 C1 C12 C13 . . . . -0.3(4) ?
C1 C12 C13 C14 . . . . -0.4(4) ?
C12 C13 C14 C3 . . . . 1.6(4) ?
C12 C13 C14 N1 . . . . -175.1(3) ?
C2 C3 C14 C13 . . . . -2.3(4) ?
C4 C3 C14 C13 . . . . -179.2(2) ?
C2 C3 C14 N1 . . . . 175.0(2) ?
C4 C3 C14 N1 . . . . -1.9(3) ?
C5 N1 C14 C13 . . . . -165.5(2) ?
C5 N1 C14 C3 . . . . 17.6(3) ?
N1 C5 C15 C16 . . . . -4.6(3) ?
C6 C5 C15 C16 . . . . 120.5(2) ?
C4 C5 C15 C16 . . . . -117.7(2) ?
N1 C5 C15 C20 . . . . 175.4(2) ?
C6 C5 C15 C20 . . . . -59.5(3) ?
C4 C5 C15 C20 . . . . 62.2(3) ?
C20 C15 C16 C17 . . . . 0.5(4) ?
C5 C15 C16 C17 . . . . -179.5(2) ?
C15 C16 C17 C18 . . . . 0.9(4) ?
C16 C17 C18 C19 . . . . -2.0(4) ?
C17 C18 C19 C20 . . . . 1.8(4) ?
C16 C15 C20 C19 . . . . -0.7(4) ?
C5 C15 C20 C19 . . . . 179.3(2) ?
C18 C19 C20 C15 . . . . -0.4(4) ?
C9 C8 C21 C22 . . . . 0.1(4) ?
C7 C8 C21 C22 . . . . 180.0(3) ?
C8 C21 C22 C11 . . . . 0.6(5) ?
C10 C11 C22 C21 . . . . -0.8(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H12 F1 2_646 0.99 2.44 3.419(3) 170.1 ?



