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

data_mo_d8v21698_0m
_database_code_depnum_ccdc_archive 'CCDC 2108706'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-09-09 deposited with the CCDC.	2022-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cl N'
_chemical_formula_weight         317.80

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7317(3)
_cell_length_b                   5.5110(2)
_cell_length_c                   27.4878(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.3610(10)
_cell_angle_gamma                90
_cell_volume                     1604.05(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    6433
_cell_measurement_theta_min      4.351
_cell_measurement_theta_max      54.744

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14209
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.004
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3128
_reflns_number_gt                2554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+0.4426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.60792(6) 0.29603(14) 0.20397(2) 0.0608(3) Uani 1 1 d . . . . .
N1 N 0.26337(16) 0.8536(3) 0.42182(6) 0.0380(4) Uani 1 1 d . . . . .
C1 C 0.17055(19) 0.6800(4) 0.41307(8) 0.0355(5) Uani 1 1 d . . . . .
C2 C 0.0671(2) 0.6446(4) 0.43730(9) 0.0433(5) Uani 1 1 d . . . . .
H2 H 0.0531 0.7455 0.4634 0.052 Uiso 1 1 calc R U . . .
C3 C -0.0135(2) 0.4560(4) 0.42134(9) 0.0468(6) Uani 1 1 d . . . . .
H3 H -0.0839 0.4272 0.4369 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0076(2) 0.3069(4) 0.38245(9) 0.0458(6) Uani 1 1 d . . . . .
H4 H -0.0491 0.1797 0.3723 0.055 Uiso 1 1 calc R U . . .
C5 C 0.11019(19) 0.3423(4) 0.35842(8) 0.0401(5) Uani 1 1 d . . . . .
H5 H 0.1229 0.2400 0.3323 0.048 Uiso 1 1 calc R U . . .
C6 C 0.19473(17) 0.5321(4) 0.37340(7) 0.0344(5) Uani 1 1 d . . . . .
C7 C 0.30787(17) 0.6285(4) 0.35822(7) 0.0342(5) Uani 1 1 d . . . . .
C8 C 0.34457(19) 0.8202(4) 0.38877(8) 0.0376(5) Uani 1 1 d . . . . .
H8 H 0.4162 0.9164 0.3873 0.045 Uiso 1 1 calc R U . . .
C9 C 0.37674(17) 0.5451(4) 0.31906(7) 0.0345(5) Uani 1 1 d . . . . .
C10 C 0.3493(2) 0.3321(4) 0.29283(8) 0.0439(6) Uani 1 1 d . . . . .
H10 H 0.2820 0.2353 0.2995 0.053 Uiso 1 1 calc R U . . .
C11 C 0.4182(2) 0.2573(4) 0.25703(9) 0.0460(6) Uani 1 1 d . . . . .
H11 H 0.3968 0.1128 0.2395 0.055 Uiso 1 1 calc R U . . .
C12 C 0.51792(19) 0.3958(4) 0.24732(8) 0.0415(5) Uani 1 1 d . . . . .
C13 C 0.5469(2) 0.6109(5) 0.27162(9) 0.0504(6) Uani 1 1 d . . . . .
H13 H 0.6138 0.7072 0.2644 0.060 Uiso 1 1 calc R U . . .
C14 C 0.4763(2) 0.6844(4) 0.30689(9) 0.0464(6) Uani 1 1 d . . . . .
H14 H 0.4959 0.8328 0.3232 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2733(2) 1.0431(4) 0.45897(8) 0.0428(5) Uani 1 1 d . . . . .
H15A H 0.1939 1.1342 0.4547 0.051 Uiso 1 1 calc R U . . .
H15B H 0.3404 1.1558 0.4536 0.051 Uiso 1 1 calc R U . . .
C16 C 0.30128(17) 0.9499(4) 0.51128(8) 0.0361(5) Uani 1 1 d . . . . .
C17 C 0.3713(2) 0.7422(4) 0.52393(9) 0.0463(6) Uani 1 1 d . . . . .
H17 H 0.4022 0.6524 0.4994 0.056 Uiso 1 1 calc R U . . .
C18 C 0.3964(3) 0.6652(5) 0.57255(10) 0.0565(7) Uani 1 1 d . . . . .
H18 H 0.4435 0.5230 0.5808 0.068 Uiso 1 1 calc R U . . .
C19 C 0.3524(3) 0.7971(5) 0.60891(10) 0.0574(7) Uani 1 1 d . . . . .
H19 H 0.3695 0.7451 0.6419 0.069 Uiso 1 1 calc R U . . .
C20 C 0.2838(2) 1.0038(5) 0.59671(9) 0.0556(7) Uani 1 1 d . . . . .
H20 H 0.2543 1.0944 0.6215 0.067 Uiso 1 1 calc R U . . .
C21 C 0.2576(2) 1.0804(4) 0.54824(8) 0.0451(6) Uani 1 1 d . . . . .
H21 H 0.2097 1.2220 0.5403 0.054 Uiso 1 1 calc R U . . .


_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 C12 1.740(2) . ?
N1 C8 1.370(3) . ?
N1 C1 1.374(3) . ?
N1 C15 1.452(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.419(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.447(3) . ?
C7 C8 1.367(3) . ?
C7 C9 1.475(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.384(3) . ?
C9 C14 1.400(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.371(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 C16 1.510(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.383(3) . ?
C16 C21 1.387(3) . ?
C17 C18 1.386(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.368(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?

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
C8 N1 C1 108.14(17) . . ?
C8 N1 C15 125.54(18) . . ?
C1 N1 C15 126.31(18) . . ?
N1 C1 C2 128.5(2) . . ?
N1 C1 C6 108.46(18) . . ?
C2 C1 C6 122.99(19) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 117.64(18) . . ?
C5 C6 C7 136.23(19) . . ?
C1 C6 C7 106.13(17) . . ?
C8 C7 C6 106.13(18) . . ?
C8 C7 C9 124.10(18) . . ?
C6 C7 C9 129.76(18) . . ?
C7 C8 N1 111.14(18) . . ?
C7 C8 H8 124.4 . . ?
N1 C8 H8 124.4 . . ?
C10 C9 C14 116.5(2) . . ?
C10 C9 C7 123.71(18) . . ?
C14 C9 C7 119.74(19) . . ?
C9 C10 C11 122.0(2) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 Cl1 119.97(17) . . ?
C11 C12 Cl1 119.58(18) . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 122.2(2) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
N1 C15 C16 113.92(17) . . ?
N1 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N1 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C21 118.7(2) . . ?
C17 C16 C15 122.46(19) . . ?
C21 C16 C15 118.84(19) . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.7(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

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
C8 N1 C1 C2 -179.4(2) . . . . ?
C15 N1 C1 C2 -0.4(3) . . . . ?
C8 N1 C1 C6 0.3(2) . . . . ?
C15 N1 C1 C6 179.31(18) . . . . ?
N1 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
N1 C1 C6 C5 -179.91(17) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C7 -0.5(2) . . . . ?
C2 C1 C6 C7 179.22(19) . . . . ?
C5 C6 C7 C8 179.8(2) . . . . ?
C1 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 C9 -1.4(4) . . . . ?
C1 C6 C7 C9 179.39(19) . . . . ?
C6 C7 C8 N1 -0.4(2) . . . . ?
C9 C7 C8 N1 -179.30(17) . . . . ?
C1 N1 C8 C7 0.0(2) . . . . ?
C15 N1 C8 C7 -178.97(18) . . . . ?
C8 C7 C9 C10 170.80(19) . . . . ?
C6 C7 C9 C10 -7.9(3) . . . . ?
C8 C7 C9 C14 -9.0(3) . . . . ?
C6 C7 C9 C14 172.3(2) . . . . ?
C14 C9 C10 C11 1.3(3) . . . . ?
C7 C9 C10 C11 -178.5(2) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 -2.2(4) . . . . ?
C10 C11 C12 Cl1 177.64(18) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
Cl1 C12 C13 C14 -178.36(18) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
C10 C9 C14 C13 -2.0(3) . . . . ?
C7 C9 C14 C13 177.8(2) . . . . ?
C8 N1 C15 C16 -113.8(2) . . . . ?
C1 N1 C15 C16 67.3(3) . . . . ?
N1 C15 C16 C17 31.0(3) . . . . ?
N1 C15 C16 C21 -150.55(19) . . . . ?
C21 C16 C17 C18 0.5(3) . . . . ?
C15 C16 C17 C18 179.0(2) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C15 C16 C21 C20 -178.5(2) . . . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4



