# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_2459
_database_code_depnum_ccdc_archive 'CCDC 2142747'
loop_
_audit_author_name
_audit_author_address
'hongbo wei'
;North West Agriculture and Forestry University
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-10
_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         'C18 H28 N2 O6'
_chemical_formula_sum            'C18 H28 N2 O6'
_chemical_formula_weight         368.42
_chemical_absolute_configuration unk
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.53431(4)
_cell_length_b                   11.74547(7)
_cell_length_c                   21.92815(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1940.51(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35554
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.1500
_cell_measurement_theta_min      3.7590
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43698
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.270
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  60.00   1.00    1.00    --    0.00  57.00  30.00   26
  2  ω    -15.00  40.00   1.00    1.00    --    0.00  37.00 150.00   55
  3  ω    -87.00 -17.00   1.00    1.00    --    0.00 -37.00  60.00   70
  4  ω    -22.00   9.00   1.00    1.00    --    0.00  57.00  30.00   31
  5  ω     56.00  81.00   1.00    1.00    --    0.00  77.00 -90.00   25
  6  ω     25.00  73.00   1.00    1.00    --    0.00  57.00-150.00   48
  7  ω    -25.00  22.00   1.00    1.00    --    0.00 -57.00  30.00   47
  8  ω     -8.00  19.00   1.00    1.00    --    0.00 -37.00  60.00   27
  9  ω    -30.00  50.00   1.00    1.00    --    0.00  77.00 -90.00   80
 10  ω    -86.00 -36.00   1.00    1.00    --    0.00 -37.00 -60.00   50
 11  ω     46.00  89.00   1.00    1.00    --    0.00  37.00 150.00   43
 12  ω    -88.00 -42.00   1.00    1.00    --    0.00 -57.00  30.00   46
 13  ω    -23.00  16.00   1.00    1.00    --    0.00  57.00-150.00   39
 14  ω    -80.00 -19.00   1.00    1.00    --    0.00 -37.00-120.00   61
 15  ω    -12.00  13.00   1.00    1.00    --    0.00 -37.00 -60.00   25
 16  ω     69.00  95.00   1.00    1.00    --   95.80  69.00 157.74   26
 17  ω     72.00 184.00   1.00    1.00    --   95.80  57.00 -74.47  112
 18  ω    156.00 182.00   1.00    1.00    --   95.80  58.00 -12.18   26
 19  ω    160.00 185.00   1.00    1.00    --   95.80  67.00 125.90   25
 20  ω     69.00 115.00   1.00    1.00    --   95.80  67.00 125.90   46
 21  ω     71.00  96.00   1.00    1.00    --   95.80  58.00 -12.18   25
 22  ω     72.00  98.00   1.00    1.00    --   95.80  56.00 -33.13   26
 23  ω     13.00 120.00   1.00    1.00    --   95.80 -61.00 -30.00  107
 24  ω     28.00 128.00   1.00    1.00    --   95.80 -82.00-180.00  100
 25  ω     75.00 132.00   1.00    1.00    --   95.80  45.00-120.00   57
 26  ω     72.00 106.00   1.00    1.00    --   95.80  61.00 150.00   34
 27  ω     61.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   67
 28  ω     63.00  91.00   1.00    1.00    --   95.80  82.00  30.00   28
 29  ω     99.00 185.00   1.00    1.00    --   95.80  82.00  30.00   86
 30  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 31  ω     63.00  89.00   1.00    1.00    --   95.80  81.00 -89.34   26
 32  ω    139.00 165.00   1.00    1.00    --   95.80  74.00  24.14   26
 33  ω     71.00  98.00   1.00    1.00    --   95.80  61.00  79.04   27
 34  ω     66.00  92.00   1.00    1.00    --   95.80  74.00  24.14   26
 35  ω    113.00 173.00   1.00    1.00    --   95.80  82.00  81.85   60
 36  ω    123.00 184.00   1.00    1.00    --   95.80  75.00-123.68   61
 37  ω     73.00 184.00   1.00    1.00    --   95.80  60.00   5.44  111
 38  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 39  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 40  ω     71.00 140.00   1.00    1.00    --   95.80  61.00  30.00   69
 41  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 43  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 44  ω     71.00 123.00   1.00    1.00    --   95.80  61.00-120.00   52
 45  ω     66.00  92.00   1.00    1.00    --   95.80  77.00 120.00   26
 46  ω      6.00 125.00   1.00    1.00    --   95.80 -82.00  90.00  119
 47  ω     75.00 185.00   1.00    1.00    --   95.80  45.00 120.00  110
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  81.85   25
 49  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 50  ω     76.00 169.00   1.00    1.00    --   95.80  45.00-180.00   93
 51  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -27.79   25
 52  ω     77.00 102.00   1.00    1.00    --   95.80  45.00  90.00   25
 53  ω     66.00  91.00   1.00    1.00    --   95.80  75.00-123.68   25
 54  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 55  ω     65.00  91.00   1.00    1.00    --   95.80  82.00  90.00   26
 56  ω     71.00  96.00   1.00    1.00    --   95.80  61.00-180.00   25
 57  ω     72.00 169.00   1.00    1.00    --   95.80  57.00-164.59   97
 58  ω     54.00  79.00   1.00    1.00    --   95.80 -82.00 120.00   25
 59  ω     87.00 112.00   1.00    1.00    --   95.80 -82.00 120.00   25
 60  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  ω     63.00  89.00   1.00    1.00    --   95.80  82.00-180.00   26
 62  ω     71.00 184.00   1.00    1.00    --   95.80  60.00 -51.17  113
 63  ω     65.00  90.00   1.00    1.00    --   95.80  76.00-160.46   25
 64  ω    126.00 151.00   1.00    1.00    --   95.80  56.00 -33.13   25
 65  ω    122.00 147.00   1.00    1.00    --   95.80  39.00  86.77   25
 66  ω     10.00 112.00   1.00    1.00    --   95.80 -82.00 -30.00  102
 67  ω     77.00 102.00   1.00    1.00    --   95.80  39.00  86.77   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1641494000
_diffrn_orient_matrix_UB_12      0.0622181000
_diffrn_orient_matrix_UB_13      -0.0253444000
_diffrn_orient_matrix_UB_21      0.0724586000
_diffrn_orient_matrix_UB_22      -0.0139660000
_diffrn_orient_matrix_UB_23      -0.0652424000
_diffrn_orient_matrix_UB_31      -0.0981398000
_diffrn_orient_matrix_UB_32      -0.1146312000
_diffrn_orient_matrix_UB_33      -0.0058186000
_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         0.730
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3427
_reflns_number_total             3438
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.3506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.06411(15) 0.28081(10) 0.62943(5) 0.0263(3) Uani 1 1 d . . . . .
O2 O -0.01500(19) 0.46633(11) 0.63220(7) 0.0367(3) Uani 1 1 d . . . . .
O3 O 0.32588(17) 0.22704(10) 0.55153(6) 0.0279(3) Uani 1 1 d . . . . .
O4 O -0.19505(19) 0.64153(12) 0.46800(7) 0.0382(3) Uani 1 1 d . . . . .
O5 O 0.64768(16) 0.76948(10) 0.63797(5) 0.0263(3) Uani 1 1 d . . . . .
O6 O 0.47158(19) 0.60416(11) 0.75479(5) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.22852(18) 0.41036(11) 0.57831(6) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.6197(2) 0.73072(13) 0.69799(6) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.2760(2) 0.52860(13) 0.55976(7) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.4327(2) 0.50620(14) 0.51915(7) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.498625 0.563283 0.500407 0.026 Uiso 1 1 calc R . . . .
C3 C 0.4667(2) 0.39633(14) 0.51300(7) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.558136 0.365756 0.489692 0.026 Uiso 1 1 calc R . . . .
C4 C 0.3377(2) 0.32979(14) 0.54867(7) 0.0200(3) Uani 1 1 d . . . . .
C5 C 0.0807(2) 0.39028(14) 0.61544(7) 0.0232(3) Uani 1 1 d . . . . .
C6 C -0.0973(2) 0.24138(15) 0.66320(8) 0.0264(4) Uani 1 1 d . . . . .
C7 C -0.0630(3) 0.11468(18) 0.66974(12) 0.0480(6) Uani 1 1 d . . . . .
H7A H -0.051206 0.081079 0.630033 0.072 Uiso 1 1 calc GR . . . .
H7B H -0.160518 0.079852 0.690860 0.072 Uiso 1 1 calc GR . . . .
H7C H 0.044367 0.102930 0.692449 0.072 Uiso 1 1 calc GR . . . .
C8 C -0.2595(2) 0.26158(17) 0.62409(8) 0.0308(4) Uani 1 1 d . . . . .
H8A H -0.280526 0.341923 0.620548 0.046 Uiso 1 1 calc GR . . . .
H8B H -0.360671 0.225835 0.642601 0.046 Uiso 1 1 calc GR . . . .
H8C H -0.240431 0.229799 0.584294 0.046 Uiso 1 1 calc GR . . . .
C9 C -0.1104(3) 0.2981(2) 0.72494(9) 0.0447(5) Uani 1 1 d . . . . .
H9A H -0.000674 0.288334 0.746581 0.067 Uiso 1 1 calc GR . . . .
H9B H -0.205287 0.264210 0.747812 0.067 Uiso 1 1 calc GR . . . .
H9C H -0.133504 0.377898 0.719626 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.1254(2) 0.58710(14) 0.52391(7) 0.0231(3) Uani 1 1 d . . . . .
H10A H 0.026028 0.599324 0.551278 0.028 Uiso 1 1 calc R . . . .
H10B H 0.166625 0.661240 0.510537 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0599(2) 0.52150(14) 0.46865(8) 0.0246(4) Uani 1 1 d . . . . .
H11A H 0.152406 0.521075 0.437871 0.030 Uiso 1 1 calc R . . . .
H11B H 0.037642 0.443195 0.480438 0.030 Uiso 1 1 calc R . . . .
C12 C -0.1071(2) 0.57071(15) 0.44132(8) 0.0258(4) Uani 1 1 d . . . . .
C13 C -0.1625(3) 0.52434(17) 0.38081(9) 0.0360(5) Uani 1 1 d . . . . .
H13A H -0.208107 0.448630 0.385952 0.054 Uiso 1 1 calc GR . . . .
H13B H -0.061981 0.522470 0.353922 0.054 Uiso 1 1 calc GR . . . .
H13C H -0.253024 0.572128 0.363658 0.054 Uiso 1 1 calc GR . . . .
C14 C 0.3299(2) 0.60288(14) 0.61465(7) 0.0234(3) Uani 1 1 d . . . . .
H14A H 0.350166 0.680053 0.600527 0.028 Uiso 1 1 calc R . . . .
H14B H 0.232085 0.604983 0.643376 0.028 Uiso 1 1 calc R . . . .
C15 C 0.4967(2) 0.56134(14) 0.64803(8) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.482329 0.482069 0.659410 0.029 Uiso 1 1 calc R . . . .
H15B H 0.598627 0.567131 0.621181 0.029 Uiso 1 1 calc R . . . .
C16 C 0.5276(2) 0.63247(14) 0.70453(8) 0.0236(4) Uani 1 1 d . . . . .
C17 C 0.8337(3) 0.76450(19) 0.62408(9) 0.0367(4) Uani 1 1 d . . . . .
H17A H 0.850853 0.776759 0.581202 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.879391 0.691042 0.635117 0.055 Uiso 1 1 calc GR . . . .
H17C H 0.895215 0.822377 0.646636 0.055 Uiso 1 1 calc GR . . . .
C18 C 0.6182(3) 0.81987(16) 0.74397(8) 0.0300(4) Uani 1 1 d . . . . .
H18A H 0.713615 0.872128 0.736287 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.632943 0.786523 0.783618 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.507184 0.859838 0.742364 0.045 Uiso 1 1 calc GR . . . .


_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
O1 C5 1.328(2) . ?
O1 C6 1.4971(19) . ?
O2 C5 1.205(2) . ?
O3 C4 1.212(2) . ?
O4 C12 1.214(2) . ?
O5 N2 1.4086(18) . ?
O5 C17 1.435(2) . ?
O6 C16 1.226(2) . ?
N1 C1 1.491(2) . ?
N1 C4 1.412(2) . ?
N1 C5 1.399(2) . ?
N2 C16 1.354(2) . ?
N2 C18 1.454(2) . ?
C1 C2 1.502(2) . ?
C1 C10 1.542(2) . ?
C1 C14 1.541(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.322(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.472(2) . ?
C6 C7 1.517(3) . ?
C6 C8 1.512(2) . ?
C6 C9 1.512(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.518(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(2) . ?
C12 C13 1.494(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.534(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.512(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C5 O1 C6 119.37(13) . . ?
N2 O5 C17 109.36(13) . . ?
C4 N1 C1 111.04(13) . . ?
C5 N1 C1 120.44(13) . . ?
C5 N1 C4 128.18(14) . . ?
O5 N2 C18 114.60(14) . . ?
C16 N2 O5 116.82(13) . . ?
C16 N2 C18 122.46(15) . . ?
N1 C1 C2 100.79(13) . . ?
N1 C1 C10 112.19(13) . . ?
N1 C1 C14 112.18(13) . . ?
C2 C1 C10 110.75(13) . . ?
C2 C1 C14 110.77(14) . . ?
C14 C1 C10 109.88(13) . . ?
C1 C2 H2 123.7 . . ?
C3 C2 C1 112.54(14) . . ?
C3 C2 H2 123.7 . . ?
C2 C3 H3 125.2 . . ?
C2 C3 C4 109.64(15) . . ?
C4 C3 H3 125.2 . . ?
O3 C4 N1 126.94(16) . . ?
O3 C4 C3 127.20(16) . . ?
N1 C4 C3 105.86(13) . . ?
O1 C5 N1 111.88(14) . . ?
O2 C5 O1 126.21(16) . . ?
O2 C5 N1 121.91(15) . . ?
O1 C6 C7 102.24(14) . . ?
O1 C6 C8 109.12(13) . . ?
O1 C6 C9 111.07(15) . . ?
C8 C6 C7 110.18(17) . . ?
C8 C6 C9 112.69(16) . . ?
C9 C6 C7 111.04(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 108.6 . . ?
C1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C1 114.82(14) . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 113.16(14) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
O4 C12 C11 121.77(16) . . ?
O4 C12 C13 121.69(17) . . ?
C13 C12 C11 116.50(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 108.7 . . ?
C1 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C1 114.13(14) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 109.95(14) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
O6 C16 N2 120.17(16) . . ?
O6 C16 C15 122.25(16) . . ?
N2 C16 C15 117.58(15) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_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 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.816
####################################################################### 
# 
# 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_exp_2460
_database_code_depnum_ccdc_archive 'CCDC 2142748'
loop_
_audit_author_name
_audit_author_address
'hongbo wei'
;North West Agriculture and Forestry University
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-10
_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         'C20 H24 Cl N O4'
_chemical_formula_sum            'C20 H24 Cl N O4'
_chemical_formula_weight         377.85
_chemical_absolute_configuration unk
_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_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                   12.41290(10)
_cell_length_b                   6.44320(10)
_cell_length_c                   24.3361(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.1400(10)
_cell_angle_gamma                90
_cell_volume                     1909.70(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22661
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.0840
_cell_measurement_theta_min      3.6780
_shelx_estimated_absorpt_T_max   0.670
_shelx_estimated_absorpt_T_min   0.536
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            42350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.060
_diffrn_reflns_theta_max         67.060
_diffrn_reflns_theta_min         3.629
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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    -29.00  23.00   1.00    1.00    --    0.00 -57.00   4.00   52
  2  ω     -8.00  30.00   1.00    1.00    --    0.00  57.00 146.00   38
  3  ω     72.00 101.00   1.00    1.00    --   95.80  57.00 146.00   29
  4  ω     22.00 104.00   1.00    1.00    --   95.80 -57.00   4.00   82
  5  ω     46.00  87.00   1.00    1.00    --    0.00  57.00-120.00   41
  6  ω    -18.00  24.00   1.00    1.00    --    0.00 -19.00  60.00   42
  7  ω     38.00  72.00   1.00    1.00    --    0.00  37.00  30.00   34
  8  ω     17.00  89.00   1.00    1.00    --    0.00  37.00-180.00   72
  9  ω    -23.00  40.00   1.00    1.00    --    0.00  57.00-120.00   63
 10  ω    -22.00  17.00   1.00    1.00    --    0.00  19.00 150.00   39
 11  ω    -83.00  12.00   1.00    1.00    --    0.00 -37.00-180.00   95
 12  ω    -10.00  25.00   1.00    1.00    --    0.00  37.00  30.00   35
 13  ω     59.00  85.00   1.00    1.00    --    0.00  19.00 150.00   26
 14  ω    -30.00  54.00   1.00    1.00    --    0.00  77.00 -30.00   84
 15  ω    -88.00 -29.00   1.00    1.00    --    0.00 -19.00  60.00   59
 16  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 17  ω     75.00 104.00   1.00    1.00    --   95.80  45.00 120.00   29
 18  ω     65.00  93.00   1.00    1.00    --   95.80  77.00-120.00   28
 19  ω     60.00 128.00   1.00    1.00    --   95.80 -82.00   0.00   68
 20  ω    104.00 130.00   1.00    1.00    --   95.80  45.00-120.00   26
 21  ω     68.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   60
 22  ω     63.00 122.00   1.00    1.00    --   95.80  82.00  60.00   59
 23  ω    150.00 182.00   1.00    1.00    --   95.80  82.00 150.00   32
 24  ω     75.00 100.00   1.00    1.00    --   95.80  45.00-120.00   25
 25  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 26  ω     63.00  98.00   1.00    1.00    --   95.80  82.00-150.00   35
 27  ω    105.00 184.00   1.00    1.00    --   95.80  82.00-150.00   79
 28  ω     71.00 183.00   1.00    1.00    --   95.80  61.00  30.00  112
 29  ω     73.00  99.00   1.00    1.00    --   95.80  61.00 -60.00   26
 30  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 31  ω     75.00 185.00   1.00    1.00    --   95.80  45.00 -60.00  110
 32  ω     70.00  95.00   1.00    1.00    --   95.80  62.00-137.57   25
 33  ω    140.00 181.00   1.00    1.00    --   95.80  62.00-137.57   41
 34  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 35  ω      6.00 127.00   1.00    1.00    --   95.80 -82.00 150.00  121
 36  ω    126.00 152.00   1.00    1.00    --   95.80  77.00 -60.00   26
 37  ω     34.00  59.00   1.00    1.00    --   95.80 -82.00-150.00   25
 38  ω     75.00 165.00   1.00    1.00    --   95.80  45.00 -90.00   90
 39  ω    132.00 177.00   1.00    1.00    --   95.80  79.00  45.99   45
 40  ω     75.00 156.00   1.00    1.00    --   95.80  45.00-180.00   81
 41  ω     63.00  96.00   1.00    1.00    --   95.80  82.00-180.00   33
 42  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 43  ω     77.00 103.00   1.00    1.00    --   95.80  45.00 150.00   26
 44  ω    134.00 178.00   1.00    1.00    --   95.80  45.00 150.00   44
 45  ω     69.00  95.00   1.00    1.00    --   95.80  79.00  45.99   26
 46  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 47  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00   0.00   25
 49  ω     65.00  92.00   1.00    1.00    --   95.80  77.00  90.00   27
 50  ω    111.00 183.00   1.00    1.00    --   95.80  77.00  90.00   72
 51  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 52  ω     83.00 115.00   1.00    1.00    --   95.80 -82.00 -60.00   32
 53  ω     43.00  79.00   1.00    1.00    --   95.80 -82.00 -60.00   36
 54  ω     74.00 184.00   1.00    1.00    --   95.80  51.00  58.33  110
 55  ω     71.00 175.00   1.00    1.00    --   95.80  61.00   0.00  104
 56  ω     70.00  96.00   1.00    1.00    --   95.80  64.00-174.64   26
 57  ω    126.00 151.00   1.00    1.00    --   95.80  77.00-180.00   25
 58  ω     70.00  96.00   1.00    1.00    --   95.80  62.00 121.44   26
 59  ω    159.00 184.00   1.00    1.00    --   95.80  62.00 121.44   25
 60  ω    148.00 184.00   1.00    1.00    --   95.80  52.00 -25.40   36
 61  ω     73.00  99.00   1.00    1.00    --   95.80  52.00 -25.40   26
 62  ω     74.00 100.00   1.00    1.00    --   95.80  61.00  60.00   26
 63  ω     68.00  94.00   1.00    1.00    --   95.80  70.00 -26.29   26
 64  ω     88.00 113.00   1.00    1.00    --   95.80 -82.00  60.00   25
 65  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 66  ω    125.00 164.00   1.00    1.00    --   95.80  45.00 120.00   39
 67  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 68  ω    148.00 173.00   1.00    1.00    --   95.80  75.00  -4.79   25
 69  ω     67.00  92.00   1.00    1.00    --   95.80  75.00  -4.79   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0836107000
_diffrn_orient_matrix_UB_12      0.1638191000
_diffrn_orient_matrix_UB_13      0.0111638000
_diffrn_orient_matrix_UB_21      0.0906574000
_diffrn_orient_matrix_UB_22      0.1088486000
_diffrn_orient_matrix_UB_23      0.0423496000
_diffrn_orient_matrix_UB_31      0.0281004000
_diffrn_orient_matrix_UB_32      0.1359916000
_diffrn_orient_matrix_UB_33      -0.0473700000
_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         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6431
_reflns_number_total             6817
_reflns_odcompleteness_completeness 99.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.184
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 2812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6817
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.1130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C25(H25), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C22(H22A,H22B), C23(H23A,H23B),
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C35(H35), C36(H36), C38(H38), C39(H39)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C20(H20A,H20B,
 H20C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,
 H40B,H40C)
;
_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
Cl1 Cl 1.00569(6) 0.40903(13) 0.55228(4) 0.0716(3) Uani 1 1 d . . . . .
O1 O 0.36329(12) 0.9110(3) 0.77333(6) 0.0376(4) Uani 1 1 d . . . . .
O2 O 0.25273(12) 0.8866(3) 0.68833(6) 0.0385(4) Uani 1 1 d . . . . .
O3 O 0.57832(12) 0.8593(3) 0.77045(6) 0.0365(4) Uani 1 1 d . . . . .
O4 O 0.49104(13) 0.4272(3) 0.51174(6) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.43400(13) 0.8598(2) 0.69364(6) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.41745(15) 0.8528(3) 0.63107(7) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.33841(16) 0.6775(3) 0.60684(8) 0.0282(4) Uani 1 1 d . . . . .
H2A H 0.350067 0.558740 0.631788 0.034 Uiso 1 1 calc R . . . .
H2B H 0.263269 0.723954 0.604248 0.034 Uiso 1 1 calc R . . . .
C3 C 0.35615(16) 0.6129(3) 0.54888(8) 0.0315(5) Uani 1 1 d . . . . .
H3A H 0.302992 0.506706 0.534108 0.038 Uiso 1 1 calc R . . . .
H3B H 0.343085 0.731649 0.523984 0.038 Uiso 1 1 calc R . . . .
C4 C 0.46927(16) 0.5313(3) 0.54938(8) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.55528(15) 0.5885(3) 0.60118(7) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.544672 0.494365 0.631301 0.029 Uiso 1 1 calc R . . . .
C6 C 0.53639(16) 0.8115(3) 0.62082(8) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.551494 0.909256 0.592402 0.029 Uiso 1 1 calc R . . . .
C7 C 0.61285(15) 0.8612(3) 0.67625(8) 0.0285(4) Uani 1 1 d . . . . .
H7A H 0.670751 0.758277 0.684456 0.034 Uiso 1 1 calc R . . . .
H7B H 0.646186 0.996629 0.674509 0.034 Uiso 1 1 calc R . . . .
C8 C 0.54385(16) 0.8589(3) 0.72061(7) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.34979(16) 0.8886(3) 0.72369(8) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.15042(18) 0.9283(4) 0.70846(10) 0.0413(5) Uani 1 1 d . . . . .
C11 C 0.1337(2) 0.7703(6) 0.75118(12) 0.0660(8) Uani 1 1 d . . . . .
H11A H 0.141899 0.633555 0.736874 0.099 Uiso 1 1 calc GR . . . .
H11B H 0.061258 0.785071 0.759122 0.099 Uiso 1 1 calc GR . . . .
H11C H 0.187129 0.791022 0.784911 0.099 Uiso 1 1 calc GR . . . .
C12 C 0.1533(2) 1.1465(5) 0.72989(19) 0.0961(14) Uani 1 1 d . . . . .
H12A H 0.203736 1.155218 0.765098 0.144 Uiso 1 1 calc GR . . . .
H12B H 0.081312 1.186135 0.734896 0.144 Uiso 1 1 calc GR . . . .
H12C H 0.176857 1.238088 0.703396 0.144 Uiso 1 1 calc GR . . . .
C13 C 0.0647(2) 0.8996(8) 0.65607(14) 0.0884(14) Uani 1 1 d . . . . .
H13A H 0.077350 0.997171 0.628178 0.133 Uiso 1 1 calc GR . . . .
H13B H -0.006840 0.922465 0.664415 0.133 Uiso 1 1 calc GR . . . .
H13C H 0.069013 0.760958 0.642223 0.133 Uiso 1 1 calc GR . . . .
C14 C 0.67006(16) 0.5496(3) 0.59035(7) 0.0266(4) Uani 1 1 d . . . . .
C15 C 0.71502(19) 0.3519(3) 0.59828(9) 0.0356(5) Uani 1 1 d . . . . .
H15 H 0.675405 0.247353 0.611714 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8178(2) 0.3066(4) 0.58663(10) 0.0434(6) Uani 1 1 d . . . . .
H16 H 0.846934 0.173579 0.592399 0.052 Uiso 1 1 calc R . . . .
C17 C 0.87566(19) 0.4612(4) 0.56647(10) 0.0418(6) Uani 1 1 d . . . . .
C18 C 0.83342(19) 0.6604(4) 0.55784(11) 0.0448(6) Uani 1 1 d . . . . .
H18 H 0.873494 0.764366 0.544447 0.054 Uiso 1 1 calc R . . . .
C19 C 0.73053(17) 0.7023(4) 0.56950(9) 0.0364(5) Uani 1 1 d . . . . .
H19 H 0.701387 0.835152 0.563250 0.044 Uiso 1 1 calc R . . . .
C20 C 0.37897(18) 1.0655(3) 0.60671(8) 0.0332(5) Uani 1 1 d . . . . .
H20A H 0.306338 1.092775 0.613067 0.050 Uiso 1 1 calc GR . . . .
H20B H 0.378240 1.066179 0.567188 0.050 Uiso 1 1 calc GR . . . .
H20C H 0.428239 1.170889 0.624603 0.050 Uiso 1 1 calc GR . . . .
Cl2 Cl -0.00353(5) -0.04573(13) 0.94762(3) 0.0633(2) Uani 1 1 d . . . . .
O5 O 0.42285(12) 0.3847(2) 0.73063(5) 0.0329(3) Uani 1 1 d . . . . .
O6 O 0.50739(13) -0.0478(3) 0.98485(6) 0.0413(4) Uani 1 1 d . . . . .
O7 O 0.75015(11) 0.4035(2) 0.80878(6) 0.0315(3) Uani 1 1 d . . . . .
O8 O 0.63873(11) 0.3327(3) 0.72553(5) 0.0316(3) Uani 1 1 d . . . . .
N2 N 0.56978(12) 0.3728(2) 0.80607(6) 0.0223(3) Uani 1 1 d . . . . .
C21 C 0.58879(15) 0.3853(3) 0.86882(7) 0.0237(4) Uani 1 1 d . . . . .
C22 C 0.66661(16) 0.2121(3) 0.89539(8) 0.0286(4) Uani 1 1 d . . . . .
H22A H 0.657256 0.091735 0.870974 0.034 Uiso 1 1 calc R . . . .
H22B H 0.741981 0.258936 0.899383 0.034 Uiso 1 1 calc R . . . .
C23 C 0.64412(16) 0.1509(3) 0.95268(8) 0.0315(5) Uani 1 1 d . . . . .
H23A H 0.697309 0.047347 0.969234 0.038 Uiso 1 1 calc R . . . .
H23B H 0.653585 0.271679 0.976941 0.038 Uiso 1 1 calc R . . . .
C24 C 0.53062(16) 0.0658(3) 0.94948(7) 0.0272(4) Uani 1 1 d . . . . .
C25 C 0.44626(15) 0.1315(3) 0.89780(7) 0.0248(4) Uani 1 1 d . . . . .
H25 H 0.456151 0.039906 0.867015 0.030 Uiso 1 1 calc R . . . .
C26 C 0.47002(15) 0.3552(3) 0.88046(7) 0.0246(4) Uani 1 1 d . . . . .
H26 H 0.459135 0.450992 0.910194 0.030 Uiso 1 1 calc R . . . .
C27 C 0.39474(16) 0.4192(3) 0.82583(8) 0.0309(5) Uani 1 1 d . . . . .
H27A H 0.329103 0.333942 0.818980 0.037 Uiso 1 1 calc R . . . .
H27B H 0.373142 0.563373 0.827522 0.037 Uiso 1 1 calc R . . . .
C28 C 0.45947(15) 0.3884(3) 0.78029(7) 0.0244(4) Uani 1 1 d . . . . .
C29 C 0.65299(15) 0.3664(3) 0.77495(8) 0.0240(4) Uani 1 1 d . . . . .
C30 C 0.85382(16) 0.3603(4) 0.78997(10) 0.0363(5) Uani 1 1 d . . . . .
C31 C 0.9387(2) 0.4233(6) 0.84078(11) 0.0556(7) Uani 1 1 d . . . . .
H31A H 0.929988 0.567716 0.848571 0.083 Uiso 1 1 calc GR . . . .
H31B H 1.010989 0.400026 0.833418 0.083 Uiso 1 1 calc GR . . . .
H31C H 0.928879 0.341987 0.872495 0.083 Uiso 1 1 calc GR . . . .
C32 C 0.8592(2) 0.1305(4) 0.77800(13) 0.0565(7) Uani 1 1 d . . . . .
H32A H 0.843058 0.053040 0.809117 0.085 Uiso 1 1 calc GR . . . .
H32B H 0.931558 0.095706 0.772447 0.085 Uiso 1 1 calc GR . . . .
H32C H 0.806507 0.097032 0.744857 0.085 Uiso 1 1 calc GR . . . .
C33 C 0.86479(18) 0.4946(4) 0.74052(9) 0.0456(6) Uani 1 1 d . . . . .
H33A H 0.814008 0.448165 0.707961 0.068 Uiso 1 1 calc GR . . . .
H33B H 0.938325 0.484841 0.733801 0.068 Uiso 1 1 calc GR . . . .
H33C H 0.848999 0.636219 0.748342 0.068 Uiso 1 1 calc GR . . . .
C34 C 0.33101(16) 0.0956(3) 0.90795(7) 0.0264(4) Uani 1 1 d . . . . .
C35 C 0.27224(17) 0.2474(4) 0.93021(9) 0.0355(5) Uani 1 1 d . . . . .
H35 H 0.302248 0.379359 0.937065 0.043 Uiso 1 1 calc R . . . .
C36 C 0.16955(19) 0.2057(4) 0.94240(10) 0.0429(6) Uani 1 1 d . . . . .
H36 H 0.130715 0.308922 0.956915 0.051 Uiso 1 1 calc R . . . .
C37 C 0.12587(18) 0.0085(4) 0.93264(9) 0.0394(5) Uani 1 1 d . . . . .
C38 C 0.1818(2) -0.1440(4) 0.91081(11) 0.0454(6) Uani 1 1 d . . . . .
H38 H 0.151570 -0.275725 0.904051 0.055 Uiso 1 1 calc R . . . .
C39 C 0.28415(19) -0.0995(3) 0.89888(10) 0.0393(5) Uani 1 1 d . . . . .
H39 H 0.322401 -0.203655 0.884388 0.047 Uiso 1 1 calc R . . . .
C40 C 0.62988(18) 0.6005(3) 0.88946(8) 0.0323(5) Uani 1 1 d . . . . .
H40A H 0.700673 0.624715 0.880312 0.048 Uiso 1 1 calc GR . . . .
H40B H 0.635620 0.608159 0.929314 0.048 Uiso 1 1 calc GR . . . .
H40C H 0.579148 0.703900 0.871706 0.048 Uiso 1 1 calc GR . . . .


_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 C17 1.747(2) . ?
O1 C9 1.196(2) . ?
O2 C9 1.338(2) . ?
O2 C10 1.472(2) . ?
O3 C8 1.206(2) . ?
O4 C4 1.208(2) . ?
N1 C1 1.497(2) . ?
N1 C8 1.394(2) . ?
N1 C9 1.399(2) . ?
C1 C2 1.537(3) . ?
C1 C6 1.567(3) . ?
C1 C20 1.533(3) . ?
C2 C3 1.527(3) . ?
C3 C4 1.497(3) . ?
C4 C5 1.531(2) . ?
C5 C6 1.546(3) . ?
C5 C14 1.519(3) . ?
C6 C7 1.526(2) . ?
C7 C8 1.502(3) . ?
C10 C11 1.498(4) . ?
C10 C12 1.498(4) . ?
C10 C13 1.506(4) . ?
C14 C15 1.389(3) . ?
C14 C19 1.392(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.373(4) . ?
C17 C18 1.387(4) . ?
C18 C19 1.387(3) . ?
Cl2 C37 1.750(2) . ?
O5 C28 1.206(2) . ?
O6 C24 1.207(2) . ?
O7 C29 1.344(2) . ?
O7 C30 1.473(2) . ?
O8 C29 1.201(2) . ?
N2 C21 1.502(2) . ?
N2 C28 1.395(2) . ?
N2 C29 1.394(2) . ?
C21 C22 1.535(3) . ?
C21 C26 1.566(3) . ?
C21 C40 1.529(3) . ?
C22 C23 1.526(3) . ?
C23 C24 1.500(3) . ?
C24 C25 1.533(2) . ?
C25 C26 1.546(3) . ?
C25 C34 1.516(3) . ?
C26 C27 1.526(3) . ?
C27 C28 1.502(3) . ?
C30 C31 1.517(3) . ?
C30 C32 1.513(3) . ?
C30 C33 1.510(3) . ?
C34 C35 1.391(3) . ?
C34 C39 1.385(3) . ?
C35 C36 1.390(3) . ?
C36 C37 1.384(4) . ?
C37 C38 1.368(4) . ?
C38 C39 1.387(3) . ?

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
C9 O2 C10 120.78(16) . . ?
C8 N1 C1 114.08(15) . . ?
C8 N1 C9 121.07(15) . . ?
C9 N1 C1 124.47(15) . . ?
N1 C1 C2 111.37(15) . . ?
N1 C1 C6 102.63(14) . . ?
N1 C1 C20 109.73(15) . . ?
C2 C1 C6 111.43(15) . . ?
C20 C1 C2 112.38(16) . . ?
C20 C1 C6 108.85(15) . . ?
C3 C2 C1 111.06(16) . . ?
C4 C3 C2 112.99(15) . . ?
O4 C4 C3 122.40(17) . . ?
O4 C4 C5 122.38(18) . . ?
C3 C4 C5 115.22(16) . . ?
C4 C5 C6 110.79(16) . . ?
C14 C5 C4 110.23(15) . . ?
C14 C5 C6 114.23(16) . . ?
C5 C6 C1 114.26(15) . . ?
C7 C6 C1 105.54(15) . . ?
C7 C6 C5 111.28(16) . . ?
C8 C7 C6 106.83(15) . . ?
O3 C8 N1 126.74(18) . . ?
O3 C8 C7 125.60(18) . . ?
N1 C8 C7 107.65(15) . . ?
O1 C9 O2 125.71(19) . . ?
O1 C9 N1 124.82(18) . . ?
O2 C9 N1 109.47(16) . . ?
O2 C10 C11 110.6(2) . . ?
O2 C10 C12 108.8(2) . . ?
O2 C10 C13 102.1(2) . . ?
C11 C10 C13 109.5(3) . . ?
C12 C10 C11 113.2(3) . . ?
C12 C10 C13 112.1(3) . . ?
C15 C14 C5 119.50(18) . . ?
C15 C14 C19 117.94(19) . . ?
C19 C14 C5 122.45(18) . . ?
C14 C15 C16 121.6(2) . . ?
C17 C16 C15 118.9(2) . . ?
C16 C17 Cl1 119.8(2) . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 Cl1 119.0(2) . . ?
C17 C18 C19 119.0(2) . . ?
C18 C19 C14 121.3(2) . . ?
C29 O7 C30 120.69(15) . . ?
C28 N2 C21 113.65(15) . . ?
C29 N2 C21 124.52(15) . . ?
C29 N2 C28 121.56(15) . . ?
N2 C21 C22 110.60(15) . . ?
N2 C21 C26 102.06(14) . . ?
N2 C21 C40 111.08(15) . . ?
C22 C21 C26 111.82(15) . . ?
C40 C21 C22 112.24(16) . . ?
C40 C21 C26 108.59(16) . . ?
C23 C22 C21 111.19(16) . . ?
C24 C23 C22 112.51(16) . . ?
O6 C24 C23 122.43(17) . . ?
O6 C24 C25 122.25(18) . . ?
C23 C24 C25 115.32(16) . . ?
C24 C25 C26 110.21(16) . . ?
C34 C25 C24 109.92(15) . . ?
C34 C25 C26 115.00(16) . . ?
C25 C26 C21 113.61(15) . . ?
C27 C26 C21 104.38(14) . . ?
C27 C26 C25 111.86(16) . . ?
C28 C27 C26 106.39(15) . . ?
O5 C28 N2 126.59(18) . . ?
O5 C28 C27 126.15(18) . . ?
N2 C28 C27 107.22(15) . . ?
O7 C29 N2 109.46(15) . . ?
O8 C29 O7 125.93(18) . . ?
O8 C29 N2 124.61(17) . . ?
O7 C30 C31 101.95(18) . . ?
O7 C30 C32 108.58(18) . . ?
O7 C30 C33 110.98(18) . . ?
C32 C30 C31 111.7(2) . . ?
C33 C30 C31 109.9(2) . . ?
C33 C30 C32 113.2(2) . . ?
C35 C34 C25 122.57(18) . . ?
C39 C34 C25 119.56(19) . . ?
C39 C34 C35 117.69(19) . . ?
C36 C35 C34 121.2(2) . . ?
C37 C36 C35 119.1(2) . . ?
C36 C37 Cl2 119.50(19) . . ?
C38 C37 Cl2 119.53(19) . . ?
C38 C37 C36 121.0(2) . . ?
C37 C38 C39 119.2(2) . . ?
C34 C39 C38 121.9(2) . . ?

_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.566
