# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_msl2_26_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2131834'
loop_
_audit_author_name
_audit_author_address
'Ming Siliang'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-12-31 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Cl N2 O2'
_chemical_formula_sum            'C21 H17 Cl N2 O2'
_chemical_formula_weight         364.82
_chemical_absolute_configuration ad
_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      monoclinic
_space_group_IT_number           4
_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                   5.7040(5)
_cell_length_b                   17.4146(15)
_cell_length_c                   9.2460(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.371(3)
_cell_angle_gamma                90
_cell_volume                     906.17(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6142
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5180
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.6947.
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    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15322
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         3.234
_diffrn_ambient_temperature      149.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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         0.930
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3396
_reflns_number_total             4155
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.027
_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)+(0.0500P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C15(H15)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.1911(2) 0.82177(6) 0.13102(15) 0.0461(3) Uani 1 1 d . U . . .
O1 O 0.5710(5) 0.43079(18) 0.6564(3) 0.0364(7) Uani 1 1 d . U . . .
O2 O 0.6530(4) 0.43647(16) 0.3391(3) 0.0268(6) Uani 1 1 d . U . . .
N1 N 0.4958(6) 0.49008(19) 0.9387(3) 0.0252(6) Uani 1 1 d . U . . .
N2 N 0.1746(6) 0.54955(19) 0.8181(4) 0.0272(7) Uani 1 1 d . U . . .
C1 C 0.3988(8) 0.5309(2) 1.0395(4) 0.0303(8) Uani 1 1 d . U . . .
H1 H 0.454984 0.533632 1.141933 0.036 Uiso 1 1 calc R . . . .
C2 C 0.3551(7) 0.5030(2) 0.8060(4) 0.0223(7) Uani 1 1 d . U . . .
C3 C 0.3998(7) 0.4712(2) 0.6656(4) 0.0239(7) Uani 1 1 d . U . . .
C4 C 0.2283(7) 0.4951(2) 0.5351(4) 0.0226(7) Uani 1 1 d . U . . .
H4 H 0.060785 0.504151 0.549943 0.027 Uiso 1 1 calc R . . . .
C5 C 0.2641(7) 0.4683(2) 0.3844(4) 0.0212(7) Uani 1 1 d . U . . .
H5 H 0.113677 0.463026 0.312602 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4592(6) 0.4134(2) 0.3581(4) 0.0207(6) Uani 1 1 d . U . . .
C7 C 0.3905(6) 0.3308(2) 0.3384(4) 0.0220(7) Uani 1 1 d . U . . .
C8 C 0.1912(7) 0.3010(2) 0.3876(5) 0.0282(8) Uani 1 1 d . U . . .
H8 H 0.096951 0.333236 0.438001 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1295(8) 0.2243(2) 0.3634(5) 0.0337(9) Uani 1 1 d . U . . .
H9 H -0.005539 0.203982 0.398128 0.040 Uiso 1 1 calc R . . . .
C10 C 0.2651(8) 0.1778(2) 0.2886(5) 0.0351(9) Uani 1 1 d . U . . .
H10 H 0.221526 0.125545 0.270696 0.042 Uiso 1 1 calc R . . . .
C11 C -0.0449(7) 0.7433(2) 0.2218(5) 0.0266(8) Uani 1 1 d . U . . .
C12 C 0.1868(8) 0.7518(2) 0.2936(5) 0.0283(8) Uani 1 1 d . U . . .
H12 H 0.264883 0.800056 0.295815 0.034 Uiso 1 1 calc R . . . .
C13 C 0.3024(7) 0.6880(2) 0.3624(4) 0.0242(7) Uani 1 1 d . U . . .
H13 H 0.461105 0.693105 0.411925 0.029 Uiso 1 1 calc R . . . .
C14 C 0.1909(6) 0.6170(2) 0.3602(4) 0.0207(7) Uani 1 1 d . U . . .
C15 C 0.3279(6) 0.5496(2) 0.4281(4) 0.0210(7) Uani 1 1 d . U . . .
H15 H 0.502747 0.558987 0.453609 0.025 Uiso 1 1 calc R . . . .
C16 C 0.2037(8) 0.5672(2) 0.9638(5) 0.0314(8) Uani 1 1 d . U . . .
H16 H 0.102123 0.600357 1.006873 0.038 Uiso 1 1 calc R . . . .
C17 C 0.7086(7) 0.4411(3) 0.9715(5) 0.0325(9) Uani 1 1 d . U . . .
H17A H 0.775673 0.445520 1.075708 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.826900 0.457588 0.912126 0.049 Uiso 1 1 calc GR . . . .
H17C H 0.664620 0.387514 0.948567 0.049 Uiso 1 1 calc GR . . . .
C18 C 0.4649(8) 0.2068(2) 0.2394(5) 0.0360(9) Uani 1 1 d . U . . .
H18 H 0.558099 0.174420 0.188643 0.043 Uiso 1 1 calc R . . . .
C19 C 0.5281(7) 0.2831(2) 0.2646(5) 0.0285(8) Uani 1 1 d . U . . .
H19 H 0.665128 0.302991 0.231470 0.034 Uiso 1 1 calc R . . . .
C20 C -0.0448(7) 0.6111(2) 0.2904(4) 0.0230(7) Uani 1 1 d . U . . .
H20 H -0.125756 0.563428 0.291304 0.028 Uiso 1 1 calc R . . . .
C21 C -0.1625(7) 0.6737(2) 0.2197(4) 0.0258(8) Uani 1 1 d . U . . .
H21 H -0.321575 0.668947 0.170639 0.031 Uiso 1 1 calc R . . . .


_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 C11 1.743(4) . ?
O1 C3 1.218(5) . ?
O2 C6 1.215(4) . ?
N1 C1 1.360(5) . ?
N1 C2 1.370(5) . ?
N1 C17 1.474(5) . ?
N2 C2 1.329(5) . ?
N2 C16 1.365(5) . ?
C1 H1 0.9500 . ?
C1 C16 1.369(6) . ?
C2 C3 1.472(5) . ?
C3 C4 1.484(6) . ?
C4 H4 1.0000 . ?
C4 C5 1.514(5) . ?
C4 C15 1.545(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.516(5) . ?
C5 C15 1.502(5) . ?
C6 C7 1.495(5) . ?
C7 C8 1.391(5) . ?
C7 C19 1.394(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(6) . ?
C10 H10 0.9500 . ?
C10 C18 1.389(6) . ?
C11 C12 1.387(6) . ?
C11 C21 1.383(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(5) . ?
C14 C15 1.490(5) . ?
C14 C20 1.397(5) . ?
C15 H15 1.0000 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.387(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 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 C2 106.5(3) . . ?
C1 N1 C17 125.1(3) . . ?
C2 N1 C17 128.5(3) . . ?
C2 N2 C16 104.4(3) . . ?
N1 C1 H1 126.9 . . ?
N1 C1 C16 106.2(4) . . ?
C16 C1 H1 126.9 . . ?
N1 C2 C3 124.6(3) . . ?
N2 C2 N1 112.0(3) . . ?
N2 C2 C3 123.4(3) . . ?
O1 C3 C2 122.3(4) . . ?
O1 C3 C4 122.3(3) . . ?
C2 C3 C4 115.2(3) . . ?
C3 C4 H4 116.8 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 C15 115.5(3) . . ?
C5 C4 H4 116.8 . . ?
C5 C4 C15 58.8(2) . . ?
C15 C4 H4 116.8 . . ?
C4 C5 H5 114.1 . . ?
C4 C5 C6 123.7(3) . . ?
C6 C5 H5 114.1 . . ?
C15 C5 C4 61.6(2) . . ?
C15 C5 H5 114.1 . . ?
C15 C5 C6 119.1(3) . . ?
O2 C6 C5 121.5(3) . . ?
O2 C6 C7 121.8(3) . . ?
C7 C6 C5 116.2(3) . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 C19 119.6(4) . . ?
C19 C7 C6 118.3(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C18 120.4(4) . . ?
C18 C10 H10 119.8 . . ?
C12 C11 Cl1 119.4(3) . . ?
C21 C11 Cl1 119.1(3) . . ?
C21 C11 C12 121.5(4) . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(4) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 C20 118.4(3) . . ?
C20 C14 C15 122.4(3) . . ?
C4 C15 H15 113.9 . . ?
C5 C15 C4 59.6(2) . . ?
C5 C15 H15 113.9 . . ?
C14 C15 C4 122.1(3) . . ?
C14 C15 C5 122.8(3) . . ?
C14 C15 H15 113.9 . . ?
N2 C16 C1 111.0(4) . . ?
N2 C16 H16 124.5 . . ?
C1 C16 H16 124.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18 120.0 . . ?
C19 C18 C10 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C7 C19 H19 120.0 . . ?
C18 C19 C7 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C14 C20 H20 119.5 . . ?
C21 C20 C14 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C11 C21 C20 119.1(4) . . ?
C11 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?

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 C11 C12 C13 -178.5(3) . . . . ?
Cl1 C11 C21 C20 179.2(3) . . . . ?
O1 C3 C4 C5 0.4(6) . . . . ?
O1 C3 C4 C15 -66.6(5) . . . . ?
O2 C6 C7 C8 166.8(4) . . . . ?
O2 C6 C7 C19 -15.1(5) . . . . ?
N1 C1 C16 N2 0.7(5) . . . . ?
N1 C2 C3 O1 -0.9(6) . . . . ?
N1 C2 C3 C4 -178.0(3) . . . . ?
N2 C2 C3 O1 177.4(4) . . . . ?
N2 C2 C3 C4 0.4(5) . . . . ?
C1 N1 C2 N2 -0.2(4) . . . . ?
C1 N1 C2 C3 178.3(3) . . . . ?
C2 N1 C1 C16 -0.3(4) . . . . ?
C2 N2 C16 C1 -0.7(4) . . . . ?
C2 C3 C4 C5 177.5(3) . . . . ?
C2 C3 C4 C15 110.4(4) . . . . ?
C3 C4 C5 C6 4.0(5) . . . . ?
C3 C4 C5 C15 -103.6(4) . . . . ?
C3 C4 C15 C5 110.4(4) . . . . ?
C3 C4 C15 C14 -137.7(4) . . . . ?
C4 C5 C6 O2 -90.2(5) . . . . ?
C4 C5 C6 C7 97.1(4) . . . . ?
C4 C5 C15 C14 -110.8(4) . . . . ?
C5 C4 C15 C14 111.9(4) . . . . ?
C5 C6 C7 C8 -20.5(5) . . . . ?
C5 C6 C7 C19 157.6(3) . . . . ?
C6 C5 C15 C4 -114.9(4) . . . . ?
C6 C5 C15 C14 134.3(4) . . . . ?
C6 C7 C8 C9 178.1(4) . . . . ?
C6 C7 C19 C18 -177.6(4) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C8 C7 C19 C18 0.6(6) . . . . ?
C8 C9 C10 C18 1.0(7) . . . . ?
C9 C10 C18 C19 -0.4(7) . . . . ?
C10 C18 C19 C7 -0.3(6) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C11 C21 C20 -0.4(6) . . . . ?
C12 C13 C14 C15 176.5(4) . . . . ?
C12 C13 C14 C20 -1.8(6) . . . . ?
C13 C14 C15 C4 131.9(4) . . . . ?
C13 C14 C15 C5 -155.9(3) . . . . ?
C13 C14 C20 C21 2.5(6) . . . . ?
C14 C20 C21 C11 -1.4(6) . . . . ?
C15 C4 C5 C6 107.7(4) . . . . ?
C15 C5 C6 O2 -16.7(5) . . . . ?
C15 C5 C6 C7 170.6(3) . . . . ?
C15 C14 C20 C21 -175.7(3) . . . . ?
C16 N2 C2 N1 0.5(4) . . . . ?
C16 N2 C2 C3 -178.0(3) . . . . ?
C17 N1 C1 C16 -179.2(4) . . . . ?
C17 N1 C2 N2 178.7(4) . . . . ?
C17 N1 C2 C3 -2.8(6) . . . . ?
C19 C7 C8 C9 0.0(6) . . . . ?
C20 C14 C15 C4 -49.9(5) . . . . ?
C20 C14 C15 C5 22.3(5) . . . . ?
C21 C11 C12 C13 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA:acetonitrile = 1:2'
