# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201909229
_audit_block_doi                 10.5517/ccdc.csd.cc23mtn7
_database_code_depnum_ccdc_archive 'CCDC 1955469'
loop_
_audit_author_name
_audit_author_address
jianlv
;zzu
China
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2019-09-21
_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         'C22 H23 Cl N2 O3'
_chemical_formula_sum            'C22 H23 Cl N2 O3'
_chemical_formula_weight         398.87
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4Cl1
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   24.1998(14)
_cell_length_b                   12.3700(6)
_cell_length_c                   9.5879(6)
_cell_angle_alpha                90
_cell_angle_beta                 119.944(8)
_cell_angle_gamma                90
_cell_volume                     2487.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0840
_cell_measurement_theta_min      4.1430
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.781
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17070
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -37.00   1.00    1.50    --  -33.50 178.00 120.00   25
  2  ω    -47.00  -7.00   1.00    1.50    --  -33.50 -77.00   0.00   40
  3  ω    -85.00 -48.00   1.00    1.50    --  -33.50 -77.00 -30.00   37
  4  ω    -61.00 -36.00   1.00    1.50    --  -33.50 178.00-180.00   25
  5  ω   -105.00 -80.00   1.00    1.50    --  -33.50 178.00-180.00   25
  6  ω     14.00 107.00   1.00    1.50    --   36.47  37.00-150.00   93
  7  ω     74.00 100.00   1.00    1.50    --   36.47 178.00 -90.00   26
  8  ω     51.00 106.00   1.00    1.50    --   36.47  37.00 120.00   55
  9  ω     57.00 104.00   1.00    1.50    --   36.47 178.00   0.00   47
 10  ω     68.00 102.00   1.00    1.50    --   36.47 178.00 120.00   34
 11  ω     62.00 110.00   1.00    1.50    --   36.47 178.00  60.00   48
 12  ω     61.00  96.00   1.00    7.50    --  108.00-111.00 120.00   35
 13  ω     38.00 110.00   1.00    7.50    --  108.00 -94.00  30.00   72
 14  ω     42.00 137.00   1.00    7.50    --  108.00 -77.00-180.00   95
 15  ω     39.00 127.00   1.00    7.50    --  108.00 -30.00  60.00   88
 16  ω     88.00 177.00   1.00    6.00    --  108.00  30.00-120.00   89
 17  ω    152.00 177.00   1.00    6.00    --  108.00  45.00-120.00   25
 18  ω    109.00 135.00   1.00    6.00    --  108.00 111.00  60.00   26
 19  ω     39.00  90.00   1.00    6.00    --  108.00 -77.00 120.00   51
 20  ω     27.00  56.00   1.00    1.00    --   36.47  24.00 -78.00   29
 21  ω    -15.00  19.00   1.00    1.00    --    0.00 -57.00   0.00   34
 22  ω      7.00  32.00   1.00    1.00    --   36.47  19.00 120.00   25
 23  ω     54.00  80.00   1.00    1.00    --   36.47  57.00  30.00   26
 24  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 25  ω     57.00  82.00   1.00    1.00    --   36.47 178.00 150.00   25
 26  ω     69.00 105.00   1.00    1.00    --   36.47  57.00   0.00   36
 27  ω     76.00 105.00   1.00    1.00    --   36.47  77.00 120.00   29
 28  ω      0.00  31.00   1.00    1.00    --   36.47  91.00  -2.60   31
 29  ω     66.00  92.00   1.00    1.00    --   36.47  19.00 120.00   26
 30  ω     35.00  61.00   1.00    1.00    --   36.47  57.00 150.00   26
 31  ω     32.00  63.00   1.00    1.00    --   36.47  77.00  60.00   31
 32  ω     42.00 100.00   1.00    1.00    --   36.47  77.00  30.00   58
 33  ω     -9.00  16.00   1.00    1.00    --   36.47 108.00  58.07   25
 34  ω     35.00  61.00   1.00    1.00    --   36.47  57.00   0.00   26
 35  ω      9.00  34.00   1.00    1.00    --   36.47  77.00  30.00   25
 36  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 37  ω     84.00 110.00   1.00    1.00    --   36.47 178.00  90.00   26
 38  ω     14.00  40.00   1.00    1.00    --   36.47  77.00 120.00   26
 39  ω     45.00  71.00   1.00    1.00    --   36.47  57.00 -30.00   26
 40  ω     19.00  44.00   1.00    1.00    --   36.47  57.00-180.00   25
 41  ω     58.00  84.00   1.00    1.00    --   36.47 178.00-120.00   26
 42  ω    130.00 156.00   1.00    6.00    --  108.00  30.00 120.00   26
 43  ω     87.00 143.00   1.00    6.00    --  108.00  30.00  60.00   56
 44  ω     88.00 114.00   1.00    6.00    --  108.00  61.00   0.00   26
 45  ω     88.00 114.00   1.00    6.00    --  108.00  61.00 -30.00   26
 46  ω     79.00 104.00   1.00    6.00    --  108.00  77.00 -60.00   25
 47  ω     83.00 109.00   1.00    6.00    --  108.00  77.00  90.00   26
 48  ω     86.00 112.00   1.00    6.00    --  108.00  30.00 120.00   26
 49  ω     89.00 115.00   1.00    6.00    --  108.00  61.00  60.00   26
 50  ω     79.00 104.00   1.00    6.00    --  108.00  77.00  60.00   25
 51  ω    153.00 178.00   1.00    6.00    --  108.00  30.00 -30.00   25
 52  ω     79.00 104.00   1.00    6.00    --  108.00  77.00   0.00   25
 53  ω     88.00 114.00   1.00    6.00    --  108.00  45.00  90.00   26
 54  ω     88.00 118.00   1.00    6.00    --  108.00  61.00  30.00   30
 55  ω     81.00 106.00   1.00    6.00    --  108.00  74.00  28.64   25
 56  ω     88.00 114.00   1.00    6.00    --  108.00  61.00  90.00   26
 57  ω    129.00 155.00   1.00    6.00    --  108.00  77.00 -30.00   26
 58  ω     82.00 133.00   1.00    6.00    --  108.00  30.00  30.00   51
 59  ω     79.00 104.00   1.00    6.00    --  108.00  77.00 -30.00   25
 60  ω     84.00 123.00   1.00    6.00    --  108.00  30.00   0.00   39
 61  ω     88.00 124.00   1.00    6.00    --  108.00  45.00   0.00   36
 62  ω     87.00 117.00   1.00    6.00    --  108.00  42.00  -9.89   30
 63  ω     88.00 114.00   1.00    6.00    --  108.00  61.00 -60.00   26
 64  ω     79.00 105.00   1.00    6.00    --  108.00  77.00  30.00   26
 65  ω     89.00 137.00   1.00    6.00    --  108.00  45.00 -30.00   48
 66  ω     89.00 132.00   1.00    6.00    --  108.00  45.00  30.00   43
 67  ω     79.00 105.00   1.00    6.00    --  108.00  77.00   5.88   26
 68  ω     83.00 129.00   1.00    6.00    --  108.00  30.00 -30.00   46
 69  ω     83.00 129.00   1.00    6.00    --  108.00  30.00  90.00   46
 70  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 71  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 72  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 73  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 74  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 75  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 76  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 77  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 78  ω     87.00 113.00   1.00    6.00    --  108.00  42.00 110.61   26
 79  ω     85.00 111.00   1.00    6.00    --  108.00  37.00 115.89   26
 80  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 81  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 82  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 83  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 84  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 85  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 86  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 87  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 88  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
 89  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 90  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
 91  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 92  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
 93  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
 94  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
 95  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
 96  ω     86.00 112.00   1.00    6.00    --  108.00  39.00  82.69   26
 97  ω     69.00  95.00   1.00    1.00    --   36.47  57.00  30.00   26
 98  ω     41.00  67.00   1.00    1.00    --   36.47  37.00 120.00   26
 99  ω     24.00  50.00   1.00    1.00    --   36.47  57.00-180.00   26
100  ω     51.00  77.00   1.00    1.00    --   36.47  57.00   0.00   26
101  ω     24.00  50.00   1.00    1.00    --   36.47  57.00 120.00   26
102  ω     91.00 117.00   1.00    6.00    --  108.00  61.00  60.00   26
103  ω     89.00 115.00   1.00    6.00    --  108.00  45.00 -30.00   26
104  ω     84.00 110.00   1.00    6.00    --  108.00  30.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0401215000
_diffrn_orient_matrix_UB_12      0.0387657000
_diffrn_orient_matrix_UB_13      -0.1755796000
_diffrn_orient_matrix_UB_21      -0.0589977000
_diffrn_orient_matrix_UB_22      0.0085798000
_diffrn_orient_matrix_UB_23      0.0207410000
_diffrn_orient_matrix_UB_31      0.0174342000
_diffrn_orient_matrix_UB_32      0.1180243000
_diffrn_orient_matrix_UB_33      0.0561157000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                3851
_reflns_number_total             4120
_reflns_odcompleteness_completeness 99.96
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4120
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1291
_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. Restrained distances
 N2-H2
 0.87 with sigma of 0.02
 N1-H1A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16), C17(H17), C18(H18)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.13048(15) 0.3235(3) 0.3768(4) 0.0570(7) Uani 1 1 d . . . . .
H1 H 0.1258 0.3277 0.2747 0.068 Uiso 1 1 calc R . . . .
C2 C 0.08820(15) 0.3761(3) 0.4117(5) 0.0648(8) Uani 1 1 d . . . . .
C3 C 0.09403(18) 0.3752(4) 0.5608(5) 0.0769(10) Uani 1 1 d . . . . .
H3 H 0.0653 0.4125 0.5809 0.092 Uiso 1 1 calc R . . . .
C4 C 0.1432(2) 0.3180(5) 0.6795(5) 0.0871(13) Uani 1 1 d . . . . .
H4 H 0.1482 0.3161 0.7822 0.105 Uiso 1 1 calc R . . . .
C5 C 0.18577(17) 0.2625(4) 0.6484(4) 0.0672(8) Uani 1 1 d . . . . .
H5 H 0.2188 0.2233 0.7304 0.081 Uiso 1 1 calc R . . . .
C6 C 0.17976(12) 0.2647(2) 0.4978(3) 0.0472(6) Uani 1 1 d . . . . .
C7 C 0.22752(13) 0.2028(2) 0.4709(3) 0.0448(6) Uani 1 1 d . . . . .
H7 H 0.2402 0.1403 0.5434 0.054 Uiso 1 1 calc R . . . .
C8 C 0.29180(12) 0.2650(2) 0.5154(3) 0.0425(5) Uani 1 1 d . . . . .
C9 C 0.28357(13) 0.3877(3) 0.5046(3) 0.0473(6) Uani 1 1 d . . . . .
C10 C 0.34050(12) 0.2485(2) 0.6900(3) 0.0454(6) Uani 1 1 d . . . . .
C11 C 0.35587(13) 0.3484(3) 0.7660(3) 0.0525(7) Uani 1 1 d . . . . .
C12 C 0.39905(19) 0.3579(4) 0.9287(4) 0.0740(10) Uani 1 1 d . . . . .
H12 H 0.4090 0.4252 0.9789 0.089 Uiso 1 1 calc R . . . .
C13 C 0.42676(18) 0.2653(5) 1.0140(4) 0.0822(12) Uani 1 1 d . . . . .
H13 H 0.4566 0.2705 1.1230 0.099 Uiso 1 1 calc R . . . .
C14 C 0.41148(17) 0.1650(4) 0.9424(4) 0.0769(11) Uani 1 1 d . . . . .
H14 H 0.4306 0.1035 1.0034 0.092 Uiso 1 1 calc R . . . .
C15 C 0.36753(15) 0.1556(3) 0.7791(4) 0.0589(8) Uani 1 1 d . . . . .
H15 H 0.3565 0.0879 0.7304 0.071 Uiso 1 1 calc R . . . .
C16 C 0.30690(14) 0.2242(2) 0.3827(3) 0.0491(6) Uani 1 1 d . . . . .
H16 H 0.2937 0.2817 0.3021 0.059 Uiso 1 1 calc R . . . .
C17 C 0.26049(15) 0.1300(3) 0.3029(3) 0.0514(6) Uani 1 1 d . . . . .
H17 H 0.2790 0.0633 0.3637 0.062 Uiso 1 1 calc R . . . .
C18 C 0.37762(18) 0.2009(3) 0.4412(4) 0.0646(8) Uani 1 1 d . . . . .
H18 H 0.3931 0.1480 0.5288 0.078 Uiso 1 1 calc R . . . .
C19 C 0.41735(19) 0.3044(4) 0.5061(6) 0.0849(12) Uani 1 1 d . . . . .
H19A H 0.3991 0.3604 0.4266 0.127 Uiso 1 1 calc GR . . . .
H19B H 0.4603 0.2906 0.5301 0.127 Uiso 1 1 calc GR . . . .
H19C H 0.4176 0.3268 0.6023 0.127 Uiso 1 1 calc GR . . . .
C20 C 0.3861(2) 0.1534(4) 0.3051(6) 0.0866(12) Uani 1 1 d . . . . .
H20A H 0.3663 0.0835 0.2761 0.130 Uiso 1 1 calc GR . . . .
H20B H 0.4307 0.1466 0.3409 0.130 Uiso 1 1 calc GR . . . .
H20C H 0.3664 0.2004 0.2133 0.130 Uiso 1 1 calc GR . . . .
C21 C 0.24098(19) 0.1130(3) 0.1266(4) 0.0675(9) Uani 1 1 d . . . . .
C22 C 0.2308(5) -0.0137(7) -0.0670(7) 0.165(4) Uani 1 1 d . . . . .
H22A H 0.1880 0.0095 -0.1396 0.248 Uiso 1 1 calc GR . . . .
H22B H 0.2342 -0.0901 -0.0788 0.248 Uiso 1 1 calc GR . . . .
H22C H 0.2597 0.0239 -0.0912 0.248 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.02496(5) 0.44943(12) 0.25850(18) 0.1034(5) Uani 1 1 d . . . . .
N1 N 0.32214(13) 0.4295(2) 0.6539(3) 0.0547(6) Uani 1 1 d D . . . .
H1A H 0.3230(16) 0.495(2) 0.675(4) 0.050(9) Uiso 1 1 d D . . . .
N2 N 0.20300(12) 0.1585(2) 0.3094(3) 0.0498(5) Uani 1 1 d D . . . .
H2 H 0.1824(15) 0.207(2) 0.241(4) 0.049(8) Uiso 1 1 d D . . . .
O1 O 0.24940(11) 0.43953(19) 0.3835(3) 0.0594(5) Uani 1 1 d . . . . .
O2 O 0.2205(2) 0.1819(3) 0.0280(3) 0.1012(11) Uani 1 1 d . . . . .
O3 O 0.2468(2) 0.0099(3) 0.0975(4) 0.0989(11) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.386(5) . ?
C1 C6 1.384(4) . ?
C2 C3 1.365(6) . ?
C2 Cl1 1.754(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C6 C7 1.512(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.592(4) . ?
C7 N2 1.461(4) . ?
C8 C9 1.527(4) . ?
C8 C10 1.504(4) . ?
C8 C16 1.572(3) . ?
C9 N1 1.362(4) . ?
C9 O1 1.219(4) . ?
C10 C11 1.388(4) . ?
C10 C15 1.386(4) . ?
C11 C12 1.383(4) . ?
C11 N1 1.397(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.532(4) . ?
C16 C18 1.539(4) . ?
C17 H17 0.9800 . ?
C17 C21 1.526(4) . ?
C17 N2 1.466(4) . ?
C18 H18 0.9800 . ?
C18 C19 1.533(6) . ?
C18 C20 1.535(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O2 1.182(5) . ?
C21 O3 1.328(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 O3 1.453(6) . ?
N1 H1A 0.84(2) . ?
N2 H2 0.84(2) . ?

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
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.4(3) . . ?
C1 C2 Cl1 118.8(3) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 Cl1 118.2(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.4(2) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 118.6(3) . . ?
C6 C7 H7 105.9 . . ?
C6 C7 C8 115.9(2) . . ?
C8 C7 H7 105.9 . . ?
N2 C7 C6 115.5(2) . . ?
N2 C7 H7 105.9 . . ?
N2 C7 C8 106.9(2) . . ?
C9 C8 C7 112.7(2) . . ?
C9 C8 C16 109.8(2) . . ?
C10 C8 C7 110.5(2) . . ?
C10 C8 C9 102.3(2) . . ?
C10 C8 C16 119.2(2) . . ?
C16 C8 C7 102.6(2) . . ?
N1 C9 C8 108.0(2) . . ?
O1 C9 C8 126.2(3) . . ?
O1 C9 N1 125.8(3) . . ?
C11 C10 C8 108.6(2) . . ?
C15 C10 C8 131.7(3) . . ?
C15 C10 C11 119.6(3) . . ?
C10 C11 N1 109.6(2) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 N1 128.9(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.7(3) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 119.0(4) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C8 C16 H16 106.8 . . ?
C17 C16 C8 103.9(2) . . ?
C17 C16 H16 106.8 . . ?
C17 C16 C18 116.4(3) . . ?
C18 C16 C8 115.5(2) . . ?
C18 C16 H16 106.8 . . ?
C16 C17 H17 109.8 . . ?
C21 C17 C16 113.7(3) . . ?
C21 C17 H17 109.8 . . ?
N2 C17 C16 105.7(2) . . ?
N2 C17 H17 109.8 . . ?
N2 C17 C21 107.7(3) . . ?
C16 C18 H18 108.4 . . ?
C19 C18 C16 110.5(3) . . ?
C19 C18 H18 108.4 . . ?
C19 C18 C20 110.0(3) . . ?
C20 C18 C16 110.9(3) . . ?
C20 C18 H18 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C17 124.1(4) . . ?
O2 C21 O3 124.8(3) . . ?
O3 C21 C17 111.0(3) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
C9 N1 C11 111.5(3) . . ?
C9 N1 H1A 123(2) . . ?
C11 N1 H1A 125(2) . . ?
C7 N2 C17 104.1(2) . . ?
C7 N2 H2 109(2) . . ?
C17 N2 H2 110(2) . . ?
C21 O3 C22 115.0(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.84(2) 2.14(3) 2.955(4) 164(3) 4_556

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
C1 C2 C3 C4 -1.3(6) . . . . ?
C1 C6 C7 C8 94.0(3) . . . . ?
C1 C6 C7 N2 -32.1(4) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 C1 0.2(6) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C5 C6 C7 C8 -85.8(3) . . . . ?
C5 C6 C7 N2 148.1(3) . . . . ?
C6 C1 C2 C3 2.0(6) . . . . ?
C6 C1 C2 Cl1 -179.2(2) . . . . ?
C6 C7 C8 C9 -26.0(3) . . . . ?
C6 C7 C8 C10 87.8(3) . . . . ?
C6 C7 C8 C16 -144.1(2) . . . . ?
C6 C7 N2 C17 165.2(2) . . . . ?
C7 C8 C9 N1 118.0(2) . . . . ?
C7 C8 C9 O1 -63.1(3) . . . . ?
C7 C8 C10 C11 -119.0(2) . . . . ?
C7 C8 C10 C15 57.9(4) . . . . ?
C7 C8 C16 C17 -11.2(2) . . . . ?
C7 C8 C16 C18 -139.9(3) . . . . ?
C8 C7 N2 C17 34.5(3) . . . . ?
C8 C9 N1 C11 -0.1(3) . . . . ?
C8 C10 C11 C12 179.0(3) . . . . ?
C8 C10 C11 N1 -1.4(3) . . . . ?
C8 C10 C15 C14 -178.9(3) . . . . ?
C8 C16 C17 C21 150.8(3) . . . . ?
C8 C16 C17 N2 32.8(3) . . . . ?
C8 C16 C18 C19 -62.1(4) . . . . ?
C8 C16 C18 C20 175.6(3) . . . . ?
C9 C8 C10 C11 1.3(3) . . . . ?
C9 C8 C10 C15 178.1(3) . . . . ?
C9 C8 C16 C17 -131.2(2) . . . . ?
C9 C8 C16 C18 100.0(3) . . . . ?
C10 C8 C9 N1 -0.7(3) . . . . ?
C10 C8 C9 O1 178.1(3) . . . . ?
C10 C8 C16 C17 111.3(3) . . . . ?
C10 C8 C16 C18 -17.5(4) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C10 C11 N1 C9 1.0(3) . . . . ?
C11 C10 C15 C14 -2.3(4) . . . . ?
C11 C12 C13 C14 -1.5(6) . . . . ?
C12 C11 N1 C9 -179.5(3) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C10 1.1(5) . . . . ?
C15 C10 C11 C12 1.7(4) . . . . ?
C15 C10 C11 N1 -178.7(3) . . . . ?
C16 C8 C9 N1 -128.2(2) . . . . ?
C16 C8 C9 O1 50.6(3) . . . . ?
C16 C8 C10 C11 122.6(3) . . . . ?
C16 C8 C10 C15 -60.5(4) . . . . ?
C16 C17 C21 O2 -52.2(5) . . . . ?
C16 C17 C21 O3 131.2(3) . . . . ?
C16 C17 N2 C7 -42.4(3) . . . . ?
C17 C16 C18 C19 175.6(3) . . . . ?
C17 C16 C18 C20 53.3(4) . . . . ?
C17 C21 O3 C22 -178.5(6) . . . . ?
C18 C16 C17 C21 -81.0(3) . . . . ?
C18 C16 C17 N2 161.0(2) . . . . ?
C21 C17 N2 C7 -164.4(3) . . . . ?
Cl1 C2 C3 C4 179.9(4) . . . . ?
N1 C11 C12 C13 -179.3(3) . . . . ?
N2 C7 C8 C9 104.3(2) . . . . ?
N2 C7 C8 C10 -141.9(2) . . . . ?
N2 C7 C8 C16 -13.8(3) . . . . ?
N2 C17 C21 O2 64.6(5) . . . . ?
N2 C17 C21 O3 -112.0(4) . . . . ?
O1 C9 N1 C11 -179.0(3) . . . . ?
O2 C21 O3 C22 4.9(8) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.154 -0.402 316.3 62.3 ?
2 0.500 0.654 0.694 316.3 62.3 ?


_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 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.882
