# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20210629pmf-1
_database_code_depnum_ccdc_archive 'CCDC 2094247'
loop_
_audit_author_name
_audit_author_address
'Ximei Zhao'
;Ludong University
China
;
_audit_update_record             
;
2021-07-04 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H19 Cl N2 O'
_chemical_formula_sum            'C21 H19 Cl N2 O'
_chemical_formula_weight         350.83
_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 0.0181 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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9491(3)
_cell_length_b                   8.2942(2)
_cell_length_c                   11.5280(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.243(4)
_cell_angle_gamma                90
_cell_volume                     886.65(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2860
_cell_measurement_theta_min      4.0710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4700
_diffrn_reflns_point_group_measured_fraction_full 0.764
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.991
_diffrn_reflns_theta_min         4.114
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    109.00 167.00   1.00    0.46    --  106.49  19.00  90.00   58
  2  ω    101.00 177.00   1.00    0.46    --  106.49  90.00 137.00   76
  3  ω     95.00 165.00   1.00    0.46    --  106.49 125.00-120.00   70
  4  ω    144.00 178.00   1.00    0.46    --  106.49  19.00-180.00   34
  5  ω     94.00 119.00   1.00    0.46    --  106.49  19.00-180.00   25
  6  ω    -39.00 -14.00   1.00    0.46    --  -86.25  38.00 -30.00   25
  7  ω    -69.00 -43.00   1.00    0.46    --  -86.25  90.00 137.00   26
  8  ω    -74.00 -28.00   1.00    0.10    --  -48.45  90.00 137.00   46
  9  ω   -123.00 -87.00   1.00    0.46    --  -86.25 -38.00  60.00   36
 10  ω   -159.00-126.00   1.00    0.46    --  -86.25 -38.00  60.00   33
 11  ω   -144.00-118.00   1.00    0.46    --  -86.25 -90.00  23.00   26
 12  ω   -117.00 -73.00   1.00    0.10    --  -48.45-125.00  60.00   44
 13  ω     11.00  66.00   1.00    0.10    --   48.45 -90.00  23.00   55
 14  ω    -18.00   8.00   1.00    0.10    --   48.45 -90.00  23.00   26
 15  ω     34.00 105.00   1.00    0.46    --  106.49 -77.00  30.00   71
 16  ω     62.00  87.00   1.00    0.46    --  106.49 -90.00  23.00   25
 17  ω    -23.00  40.00   1.00    0.10    --   48.45 -38.00 120.00   63
 18  ω     34.00  60.00   1.00    0.46    --  106.49 -57.00 -90.00   26
 19  ω     39.00  65.00   1.00    0.46    --  106.49 -57.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0993981000
_diffrn_orient_matrix_UB_12      -0.0274418000
_diffrn_orient_matrix_UB_13      0.0742716000
_diffrn_orient_matrix_UB_21      0.0686004000
_diffrn_orient_matrix_UB_22      -0.1671548000
_diffrn_orient_matrix_UB_23      0.0406809000
_diffrn_orient_matrix_UB_31      0.1140841000
_diffrn_orient_matrix_UB_32      0.0761312000
_diffrn_orient_matrix_UB_33      0.1156356000
_diffrn_oxdiff_digest_frames     
;
01ab8c1a49781bbfd656f82170ca4e485b00791e7ca
;
_diffrn_oxdiff_digest_hkl        
;
0191ab2e84bda9e05a63d1c066bdac154d4f48
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.458
_reflns_Friedel_fraction_full    0.519
_reflns_Friedel_fraction_max     0.525
_reflns_number_gt                2364
_reflns_number_total             2445
_reflns_odcompleteness_completeness 98.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.160
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.038(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.086
_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)+(0.0458P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00D), C00I(H00F,H00G), C00J(H00I,H00J), C00K(H00K,H00L), C00N(H00O,
 H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00C(H00C), C00E(H00E), C00H(H00H), C00L(H00M),
 C00M(H00N), C00O(H00Q), C00P(H00R)
;
_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
Cl01 Cl 0.73063(5) 0.90938(7) 0.90376(6) 0.04204(18) Uani 1 1 d . . . . .
O002 O -0.10392(18) 0.5058(2) 0.87977(16) 0.0412(4) Uani 1 1 d . . . . .
N003 N 0.18938(17) 0.5474(2) 0.78770(16) 0.0234(4) Uani 1 1 d . . . . .
N004 N 0.40858(17) 0.4223(2) 0.71443(15) 0.0257(4) Uani 1 1 d . . . . .
C005 C 0.3156(2) 0.6302(3) 0.81844(18) 0.0226(4) Uani 1 1 d . . . . .
C006 C 0.5543(2) 0.6558(3) 0.8104(2) 0.0275(5) Uani 1 1 d . . . . .
H006 H 0.6295 0.6174 0.7883 0.033 Uiso 1 1 calc R . . . .
C007 C 0.0888(2) 0.6029(3) 0.82656(19) 0.0250(4) Uani 1 1 d . . . . .
C008 C 0.4292(2) 0.5657(3) 0.78156(18) 0.0234(4) Uani 1 1 d . . . . .
C009 C -0.0365(2) 0.4923(3) 0.8101(2) 0.0284(5) Uani 1 1 d . . . . .
C00A C 0.5694(2) 0.8041(3) 0.8725(2) 0.0293(5) Uani 1 1 d . . . . .
C00B C 0.4664(2) 0.8670(3) 0.9102(2) 0.0294(5) Uani 1 1 d . . . . .
H00B H 0.4805 0.9651 0.9520 0.035 Uiso 1 1 calc R . . . .
C00C C 0.2233(2) 0.8364(3) 0.9202(2) 0.0308(5) Uani 1 1 d . . . . .
H00C H 0.2330 0.9339 0.9623 0.037 Uiso 1 1 calc R . . . .
C00D C -0.0722(2) 0.3630(3) 0.7144(2) 0.0286(5) Uani 1 1 d . . . . .
C00E C 0.1004(2) 0.7485(3) 0.8931(2) 0.0310(5) Uani 1 1 d . . . . .
H00E H 0.0260 0.7832 0.9177 0.037 Uiso 1 1 calc R . . . .
C00F C 0.3709(2) 0.2756(3) 0.7687(2) 0.0279(4) Uani 1 1 d . . . . .
H00A H 0.3043 0.3030 0.8096 0.034 Uiso 1 1 calc R . . . .
H00D H 0.4571 0.2305 0.8305 0.034 Uiso 1 1 calc R . . . .
C00G C 0.3365(2) 0.7794(3) 0.88419(19) 0.0262(4) Uani 1 1 d . . . . .
C00H C -0.0723(2) 0.3911(3) 0.5948(2) 0.0327(5) Uani 1 1 d . . . . .
H00H H -0.0431 0.4906 0.5751 0.039 Uiso 1 1 calc R . . . .
C00I C 0.5119(2) 0.3858(3) 0.6545(2) 0.0339(5) Uani 1 1 d . . . . .
H00F H 0.6004 0.3452 0.7161 0.041 Uiso 1 1 calc R . . . .
H00G H 0.5345 0.4838 0.6194 0.041 Uiso 1 1 calc R . . . .
C00J C 0.3021(2) 0.1519(3) 0.6672(2) 0.0322(5) Uani 1 1 d . . . . .
H00I H 0.2132 0.1953 0.6078 0.039 Uiso 1 1 calc R . . . .
H00J H 0.2785 0.0556 0.7037 0.039 Uiso 1 1 calc R . . . .
C00K C 0.4038(3) 0.1085(3) 0.6004(2) 0.0358(5) Uani 1 1 d . . . . .
H00K H 0.3555 0.0367 0.5314 0.043 Uiso 1 1 calc R . . . .
H00L H 0.4877 0.0531 0.6573 0.043 Uiso 1 1 calc R . . . .
C00L C -0.1136(3) 0.2120(3) 0.7424(3) 0.0397(6) Uani 1 1 d . . . . .
H00M H -0.1146 0.1921 0.8214 0.048 Uiso 1 1 calc R . . . .
C00M C -0.1562(3) 0.1211(4) 0.5346(2) 0.0409(6) Uani 1 1 d . . . . .
H00N H -0.1853 0.0406 0.4745 0.049 Uiso 1 1 calc R . . . .
C00N C 0.4511(3) 0.2612(3) 0.5520(2) 0.0369(5) Uani 1 1 d . . . . .
H00O H 0.5240 0.2339 0.5177 0.044 Uiso 1 1 calc R . . . .
H00P H 0.3692 0.3069 0.4857 0.044 Uiso 1 1 calc R . . . .
C00O C -0.1159(3) 0.2705(4) 0.5055(2) 0.0375(5) Uani 1 1 d . . . . .
H00Q H -0.1181 0.2904 0.4255 0.045 Uiso 1 1 calc R . . . .
C00P C -0.1530(3) 0.0917(4) 0.6540(3) 0.0459(6) Uani 1 1 d . . . . .
H00R H -0.1776 -0.0097 0.6745 0.055 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
Cl01 C00A 1.745(2) . ?
O002 C009 1.224(3) . ?
N003 C005 1.361(3) . ?
N003 C007 1.319(3) . ?
N004 C008 1.393(3) . ?
N004 C00F 1.477(3) . ?
N004 C00I 1.463(3) . ?
C005 C008 1.446(3) . ?
C005 C00G 1.427(3) . ?
C006 H006 0.9300 . ?
C006 C008 1.385(3) . ?
C006 C00A 1.403(3) . ?
C007 C009 1.503(3) . ?
C007 C00E 1.412(3) . ?
C009 C00D 1.486(3) . ?
C00A C00B 1.355(3) . ?
C00B H00B 0.9300 . ?
C00B C00G 1.417(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.359(3) . ?
C00C C00G 1.415(3) . ?
C00D C00H 1.398(3) . ?
C00D C00L 1.393(4) . ?
C00E H00E 0.9300 . ?
C00F H00A 0.9700 . ?
C00F H00D 0.9700 . ?
C00F C00J 1.520(3) . ?
C00H H00H 0.9300 . ?
C00H C00O 1.387(4) . ?
C00I H00F 0.9700 . ?
C00I H00G 0.9700 . ?
C00I C00N 1.520(3) . ?
C00J H00I 0.9700 . ?
C00J H00J 0.9700 . ?
C00J C00K 1.521(3) . ?
C00K H00K 0.9700 . ?
C00K H00L 0.9700 . ?
C00K C00N 1.525(4) . ?
C00L H00M 0.9300 . ?
C00L C00P 1.377(4) . ?
C00M H00N 0.9300 . ?
C00M C00O 1.380(4) . ?
C00M C00P 1.387(4) . ?
C00N H00O 0.9700 . ?
C00N H00P 0.9700 . ?
C00O H00Q 0.9300 . ?
C00P H00R 0.9300 . ?

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
C007 N003 C005 118.55(18) . . ?
C008 N004 C00F 118.47(16) . . ?
C008 N004 C00I 116.86(17) . . ?
C00I N004 C00F 111.07(18) . . ?
N003 C005 C008 118.85(19) . . ?
N003 C005 C00G 121.24(18) . . ?
C00G C005 C008 119.90(18) . . ?
C008 C006 H006 119.4 . . ?
C008 C006 C00A 121.1(2) . . ?
C00A C006 H006 119.4 . . ?
N003 C007 C009 116.1(2) . . ?
N003 C007 C00E 124.06(19) . . ?
C00E C007 C009 119.42(18) . . ?
N004 C008 C005 120.38(18) . . ?
C006 C008 N004 122.22(18) . . ?
C006 C008 C005 117.3(2) . . ?
O002 C009 C007 119.2(2) . . ?
O002 C009 C00D 120.8(2) . . ?
C00D C009 C007 119.90(18) . . ?
C006 C00A Cl01 117.71(17) . . ?
C00B C00A Cl01 119.09(18) . . ?
C00B C00A C006 123.2(2) . . ?
C00A C00B H00B 120.9 . . ?
C00A C00B C00G 118.2(2) . . ?
C00G C00B H00B 120.9 . . ?
C00E C00C H00C 120.0 . . ?
C00E C00C C00G 119.9(2) . . ?
C00G C00C H00C 120.0 . . ?
C00H C00D C009 121.8(2) . . ?
C00L C00D C009 119.3(2) . . ?
C00L C00D C00H 118.9(2) . . ?
C007 C00E H00E 120.9 . . ?
C00C C00E C007 118.2(2) . . ?
C00C C00E H00E 120.9 . . ?
N004 C00F H00A 109.7 . . ?
N004 C00F H00D 109.7 . . ?
N004 C00F C00J 110.04(18) . . ?
H00A C00F H00D 108.2 . . ?
C00J C00F H00A 109.7 . . ?
C00J C00F H00D 109.7 . . ?
C00B C00G C005 120.2(2) . . ?
C00C C00G C005 117.87(19) . . ?
C00C C00G C00B 121.9(2) . . ?
C00D C00H H00H 120.0 . . ?
C00O C00H C00D 120.0(2) . . ?
C00O C00H H00H 120.0 . . ?
N004 C00I H00F 109.4 . . ?
N004 C00I H00G 109.4 . . ?
N004 C00I C00N 110.99(18) . . ?
H00F C00I H00G 108.0 . . ?
C00N C00I H00F 109.4 . . ?
C00N C00I H00G 109.4 . . ?
C00F C00J H00I 109.5 . . ?
C00F C00J H00J 109.5 . . ?
C00F C00J C00K 110.65(18) . . ?
H00I C00J H00J 108.1 . . ?
C00K C00J H00I 109.5 . . ?
C00K C00J H00J 109.5 . . ?
C00J C00K H00K 109.7 . . ?
C00J C00K H00L 109.7 . . ?
C00J C00K C00N 109.79(19) . . ?
H00K C00K H00L 108.2 . . ?
C00N C00K H00K 109.7 . . ?
C00N C00K H00L 109.7 . . ?
C00D C00L H00M 119.7 . . ?
C00P C00L C00D 120.6(2) . . ?
C00P C00L H00M 119.7 . . ?
C00O C00M H00N 120.2 . . ?
C00O C00M C00P 119.6(2) . . ?
C00P C00M H00N 120.2 . . ?
C00I C00N C00K 111.7(2) . . ?
C00I C00N H00O 109.3 . . ?
C00I C00N H00P 109.3 . . ?
C00K C00N H00O 109.3 . . ?
C00K C00N H00P 109.3 . . ?
H00O C00N H00P 107.9 . . ?
C00H C00O H00Q 119.8 . . ?
C00M C00O C00H 120.5(2) . . ?
C00M C00O H00Q 119.8 . . ?
C00L C00P C00M 120.3(3) . . ?
C00L C00P H00R 119.8 . . ?
C00M C00P H00R 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.505
