# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_16022_APM-501
_database_code_depnum_ccdc_archive 'CCDC 2085045'
loop_
_audit_author_name
_audit_author_address
'Mariya Kryukova'
;SPbSU
Russia
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 N O5'
_chemical_formula_sum            'C20 H25 N O5'
_chemical_formula_weight         359.43
_chemical_oxdiff_formula         'C20 H25 N O5 '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.5595(2)
_cell_length_b                   7.54710(10)
_cell_length_c                   18.0224(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.000(2)
_cell_angle_gamma                90
_cell_volume                     1772.87(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5210
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.0770
_cell_measurement_theta_min      3.3900
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3465
_exptl_crystal_description       needle
_exptl_crystal_F_000             770.6136
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10486
_diffrn_reflns_theta_full        70.3352
_diffrn_reflns_theta_max         70.34
_diffrn_reflns_theta_min         3.39
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -18.00   0.50    0.21    --  -38.82 137.00 166.00   64
  2  ω    -88.00 -62.00   0.50    0.21    --  -38.82 137.00 166.00   52
  3  ω     25.00  63.00   0.50    0.21    --   38.82-137.00 102.00   76
  4  ω     72.00 119.00   0.50    0.83    --  100.00-137.00 102.00   94
  5  ω     93.00 119.00   0.50    0.83    --  100.00 137.00 166.00   52
  6  ω     83.00 109.00   0.50    0.83    --  100.00-132.00 -79.00   52
  7  ω     36.00  62.00   0.50    0.83    --  100.00-137.00 102.00   52
  8  ω     90.00 140.00   0.50    0.83    --  100.00 132.00 -10.00  100
  9  ω    -71.00 -45.00   0.50    0.21    --  -38.82 132.00 -10.00   52
 10  ω    -42.00   6.00   0.50    0.21    --  -38.82 104.00 -30.00   96
 11  ω    -52.00  27.00   0.50    0.21    --  -38.82  43.00   0.00  158
 12  ω     27.00  75.00   0.50    0.21    --   38.82-104.00 -60.00   96
 13  ω     71.00 106.00   0.50    0.21    --   38.82  21.00 120.00   70
 14  ω     51.00 100.00   0.50    0.21    --   38.82  54.00-150.00   98
 15  ω     26.00  64.00   0.50    0.21    --   38.82  43.00  90.00   76
 16  ω     -4.00  23.00   0.50    0.21    --   38.82-104.00 -60.00   54
 17  ω     19.00 110.00   0.50    0.21    --   38.82  21.00-150.00  182
 18  ω     26.00 103.00   0.50    0.21    --   38.82  54.00  30.00  154
 19  ω     37.00  62.00   0.50    0.21    --   38.82-132.00 -79.00   50
 20  ω     51.00  88.00   0.50    0.21    --   38.82-138.00-180.00   74
 21  ω    121.00 147.00   0.50    0.83    --  100.00  77.00  30.00   52
 22  ω     55.00 105.00   0.50    0.83    --  100.00 -93.00  30.00  100
 23  ω     83.00 118.00   0.50    0.83    --  100.00  77.00  30.00   70
 24  ω    125.00 156.00   0.50    0.83    --  100.00  93.00  90.00   62
 25  ω     40.00  86.00   0.50    0.83    --  100.00-111.00  90.00   92
 26  ω     84.00 146.00   0.50    0.83    --  100.00 111.00  30.00  124
 27  ω     85.00 157.00   0.50    0.83    --  100.00 111.00  60.00  144
 28  ω    118.00 144.00   0.50    0.83    --  100.00  45.00 -60.00   52
 29  ω     84.00 110.00   0.50    0.83    --  100.00  45.00 -60.00   52
 30  ω     79.00 116.00   0.50    0.83    --  100.00-133.00  30.00   74
 31  ω     43.00  69.00   0.50    0.83    --  100.00-133.00  30.00   52
 32  ω     73.00 132.00   0.50    0.83    --  100.00 133.00  90.00  118
 33  ω     72.00 100.00   0.50    0.83    --  100.00  15.00  30.00   56
 34  ω    122.00 148.00   0.50    0.83    --  100.00  15.00  30.00   52
 35  ω     84.00 154.00   0.50    0.83    --  100.00 133.00 120.00  140
 36  ω     54.00  98.00   0.50    0.83    --  100.00 -86.00 150.00   88
 37  ω     83.00 108.00   0.50    0.83    --  100.00-111.00 -60.00   50
 38  ω     51.00  76.00   0.50    0.83    --  100.00-111.00  30.00   50
 39  ω     48.00 118.00   0.50    0.83    --  100.00-133.00 -90.00  140
 40  ω     35.00 122.00   0.50    0.83    --  100.00 -61.00-120.00  174
 41  ω     54.00  97.00   0.50    0.83    --  100.00 -93.00 -90.00   86
 42  ω     93.00 155.00   0.50    0.83    --  100.00 111.00-150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0663382000
_diffrn_orient_matrix_UB_12      -0.1432669000
_diffrn_orient_matrix_UB_13      -0.0237735000
_diffrn_orient_matrix_UB_21      0.0636913000
_diffrn_orient_matrix_UB_22      0.1454288000
_diffrn_orient_matrix_UB_23      -0.0251791000
_diffrn_orient_matrix_UB_31      0.0742656000
_diffrn_orient_matrix_UB_32      0.0031192000
_diffrn_orient_matrix_UB_33      0.0818858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2954
_reflns_number_total             3378
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2503
_refine_diff_density_min         -0.2486
_refine_diff_density_rms         0.0482
_refine_ls_d_res_high            0.8187
_refine_ls_d_res_low             13.0342
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.0359
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.6958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0911
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b), C7(H7a,H7b), C8(H8a,H8b), C5(H5a,H5b), C6(H6a,H6b)
2.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C14(H14), C13(H13)
2.e Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C18(H18a,H18b,H18c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O5 O 0.67810(7) 0.70415(13) 0.30843(5) 0.0192(2) Uani 1.000000 .
O2 O 0.92389(7) 0.26446(13) 0.51512(6) 0.0218(2) Uani 1.000000 .
O4 O 0.89592(7) 0.50864(14) 0.34114(6) 0.0246(2) Uani 1.000000 .
O1 O 0.76074(7) 0.22746(14) 0.51944(6) 0.0263(2) Uani 1.000000 .
O3 O 0.82126(8) 0.24282(14) 0.34284(6) 0.0263(2) Uani 1.000000 .
N1 N 0.84885(8) 0.61547(14) 0.47063(6) 0.0154(2) Uani 1.000000 .
H1 H 0.91467(8) 0.60759(14) 0.48371(6) 0.0185(3) Uiso 1.000000 R
C11 C 0.81197(10) 0.68684(17) 0.53176(7) 0.0153(3) Uani 1.000000 .
C2 C 0.68263(9) 0.48720(17) 0.40616(7) 0.0145(3) Uani 1.000000 .
H2 H 0.65687(9) 0.48978(17) 0.45189(7) 0.0174(3) Uiso 1.000000 R
C12 C 0.72158(10) 0.78798(17) 0.51263(7) 0.0148(3) Uani 1.000000 .
C10 C 0.67680(9) 0.67628(17) 0.37468(7) 0.0144(3) Uani 1.000000 .
C9 C 0.66731(9) 0.82627(17) 0.42813(7) 0.0151(3) Uani 1.000000 .
H9 H 0.70105(9) 0.92978(17) 0.41316(7) 0.0181(3) Uiso 1.000000 R
C3 C 0.61678(10) 0.35450(17) 0.34920(7) 0.0171(3) Uani 1.000000 .
H3a H 0.62445(10) 0.37683(17) 0.29808(7) 0.0205(3) Uiso 1.000000 R
H3b H 0.64128(10) 0.23545(17) 0.36415(7) 0.0205(3) Uiso 1.000000 R
C15 C 0.83479(11) 0.74367(19) 0.66722(8) 0.0206(3) Uani 1.000000 .
H15 H 0.87334(11) 0.73192(19) 0.71835(8) 0.0247(3) Uiso 1.000000 R
C16 C 0.86762(10) 0.66405(18) 0.60871(8) 0.0189(3) Uani 1.000000 .
H16 H 0.92687(10) 0.59539(18) 0.62088(8) 0.0227(3) Uiso 1.000000 R
C4 C 0.50252(10) 0.36623(18) 0.34622(7) 0.0174(3) Uani 1.000000 .
H4a H 0.46755(10) 0.26571(18) 0.31694(7) 0.0209(3) Uiso 1.000000 R
H4b H 0.49676(10) 0.35431(18) 0.39846(7) 0.0209(3) Uiso 1.000000 R
C14 C 0.74458(11) 0.84053(19) 0.64930(8) 0.0204(3) Uani 1.000000 .
H14 H 0.72146(11) 0.89167(19) 0.68837(8) 0.0245(3) Uiso 1.000000 R
C1 C 0.80001(9) 0.45147(17) 0.43428(7) 0.0151(3) Uani 1.000000 .
C7 C 0.48368(10) 0.72976(18) 0.43490(7) 0.0171(3) Uani 1.000000 .
H7a H 0.52761(10) 0.63647(18) 0.46301(7) 0.0206(3) Uiso 1.000000 R
H7b H 0.44869(10) 0.78285(18) 0.46963(7) 0.0206(3) Uiso 1.000000 R
C17 C 0.84534(10) 0.40864(18) 0.36727(7) 0.0177(3) Uani 1.000000 .
C8 C 0.55174(10) 0.87243(17) 0.41189(7) 0.0165(3) Uani 1.000000 .
H8a H 0.54586(10) 0.98099(17) 0.43916(7) 0.0198(3) Uiso 1.000000 R
H8b H 0.52458(10) 0.89609(17) 0.35713(7) 0.0198(3) Uiso 1.000000 R
C19 C 0.82241(10) 0.29876(17) 0.49309(7) 0.0166(3) Uani 1.000000 .
C13 C 0.68884(10) 0.86086(18) 0.57263(7) 0.0178(3) Uani 1.000000 .
H13 H 0.62794(10) 0.92499(18) 0.56110(7) 0.0213(3) Uiso 1.000000 R
C5 C 0.44507(10) 0.53658(18) 0.31087(7) 0.0179(3) Uani 1.000000 .
H5a H 0.49142(10) 0.61000(18) 0.29171(7) 0.0215(3) Uiso 1.000000 R
H5b H 0.38837(10) 0.50378(18) 0.26707(7) 0.0215(3) Uiso 1.000000 R
C6 C 0.40320(10) 0.64641(19) 0.36674(8) 0.0192(3) Uani 1.000000 .
H6a H 0.35892(10) 0.57115(19) 0.38720(8) 0.0231(3) Uiso 1.000000 R
H6b H 0.36102(10) 0.74065(19) 0.33778(8) 0.0231(3) Uiso 1.000000 R
C20 C 0.95707(12) 0.1343(2) 0.57615(9) 0.0286(3) Uani 1.000000 .
H20a H 0.9233(7) 0.0236(5) 0.5597(3) 0.0429(5) Uiso 1.000000 GR
H20b H 1.02997(18) 0.1184(12) 0.5876(5) 0.0429(5) Uiso 1.000000 GR
H20c H 0.9399(8) 0.1748(8) 0.6215(2) 0.0429(5) Uiso 1.000000 GR
C18 C 0.85567(12) 0.1868(3) 0.27744(10) 0.0362(4) Uani 1.000000 .
H18a H 0.8372(9) 0.2747(9) 0.2375(3) 0.0542(6) Uiso 1.000000 GR
H18b H 0.92885(17) 0.1724(18) 0.2931(2) 0.0542(6) Uiso 1.000000 GR
H18c H 0.8238(8) 0.0761(9) 0.2583(5) 0.0542(6) Uiso 1.000000 GR


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
O5 C10 1.2174(16) . ?
O2 C19 1.3479(16) . ?
O2 C20 1.4506(16) . ?
O4 C17 1.2000(17) . ?
O1 C19 1.1972(17) . ?
O3 C17 1.3370(17) . ?
O3 C18 1.4452(18) . ?
N1 H1 0.8600 . ?
N1 C11 1.4345(17) . ?
N1 C1 1.4699(16) . ?
C11 C12 1.4038(19) . ?
C11 C16 1.3947(18) . ?
C2 H2 0.9800 . ?
C2 C10 1.5296(17) . ?
C2 C3 1.5326(17) . ?
C2 C1 1.5550(17) . ?
C12 C9 1.5252(17) . ?
C12 C13 1.3906(18) . ?
C10 C9 1.5147(17) . ?
C9 H9 0.9800 . ?
C9 C8 1.5525(17) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.5379(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(2) . ?
C15 C14 1.385(2) . ?
C16 H16 0.9300 . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C4 C5 1.5467(18) . ?
C14 H14 0.9300 . ?
C14 C13 1.3886(19) . ?
C1 C17 1.5330(17) . ?
C1 C19 1.5383(18) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C8 1.5473(18) . ?
C7 C6 1.5351(18) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C13 H13 0.9300 . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C5 C6 1.5293(18) . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C20 H20a 0.9600 . ?
C20 H20b 0.9600 . ?
C20 H20c 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
C20 O2 C19 115.56(11) . . ?
C18 O3 C17 115.97(13) . . ?
C11 N1 H1 111.8 . . ?
C1 N1 H1 111.71(6) . . ?
C1 N1 C11 116.67(10) . . ?
C12 C11 N1 118.75(11) . . ?
C16 C11 N1 120.64(12) . . ?
C16 C11 C12 120.52(12) . . ?
C10 C2 H2 107.42(7) . . ?
C3 C2 H2 107.42(7) . . ?
C3 C2 C10 113.59(10) . . ?
C1 C2 H2 107.42(6) . . ?
C1 C2 C10 103.08(10) . . ?
C1 C2 C3 117.39(10) . . ?
C9 C12 C11 119.77(11) . . ?
C13 C12 C11 117.92(12) . . ?
C13 C12 C9 122.14(12) . . ?
C2 C10 O5 120.78(11) . . ?
C9 C10 O5 121.43(12) . . ?
C9 C10 C2 117.78(10) . . ?
C10 C9 C12 113.03(10) . . ?
H9 C9 C12 107.02(7) . . ?
H9 C9 C10 107.02(7) . . ?
C8 C9 C12 114.52(10) . . ?
C8 C9 C10 107.82(10) . . ?
C8 C9 H9 107.02(7) . . ?
H3a C3 C2 109.12(7) . . ?
H3b C3 C2 109.12(7) . . ?
H3b C3 H3a 107.9 . . ?
C4 C3 C2 112.40(10) . . ?
C4 C3 H3a 109.12(7) . . ?
C4 C3 H3b 109.12(7) . . ?
C16 C15 H15 120.05(8) . . ?
C14 C15 H15 120.05(8) . . ?
C14 C15 C16 119.91(12) . . ?
C15 C16 C11 120.17(13) . . ?
H16 C16 C11 119.91(8) . . ?
H16 C16 C15 119.91(8) . . ?
H4a C4 C3 108.10(7) . . ?
H4b C4 C3 108.10(7) . . ?
H4b C4 H4a 107.3 . . ?
C5 C4 C3 116.77(11) . . ?
C5 C4 H4a 108.10(7) . . ?
C5 C4 H4b 108.10(7) . . ?
H14 C14 C15 120.20(8) . . ?
C13 C14 C15 119.60(13) . . ?
C13 C14 H14 120.20(8) . . ?
C2 C1 N1 107.11(10) . . ?
C17 C1 N1 107.42(10) . . ?
C17 C1 C2 112.12(10) . . ?
C19 C1 N1 110.16(10) . . ?
C19 C1 C2 110.15(10) . . ?
C19 C1 C17 109.81(10) . . ?
H7b C7 H7a 107.6 . . ?
C8 C7 H7a 108.62(7) . . ?
C8 C7 H7b 108.62(7) . . ?
C6 C7 H7a 108.62(7) . . ?
C6 C7 H7b 108.62(7) . . ?
C6 C7 C8 114.56(11) . . ?
O3 C17 O4 125.00(13) . . ?
C1 C17 O4 124.98(12) . . ?
C1 C17 O3 110.02(11) . . ?
C7 C8 C9 116.04(10) . . ?
H8a C8 C9 108.28(7) . . ?
H8a C8 C7 108.28(7) . . ?
H8b C8 C9 108.28(7) . . ?
H8b C8 C7 108.28(7) . . ?
H8b C8 H8a 107.4 . . ?
O1 C19 O2 124.39(12) . . ?
C1 C19 O2 109.79(11) . . ?
C1 C19 O1 125.67(12) . . ?
C14 C13 C12 121.82(13) . . ?
H13 C13 C12 119.09(8) . . ?
H13 C13 C14 119.09(8) . . ?
H5a C5 C4 108.62(7) . . ?
H5b C5 C4 108.62(7) . . ?
H5b C5 H5a 107.6 . . ?
C6 C5 C4 114.55(11) . . ?
C6 C5 H5a 108.62(7) . . ?
C6 C5 H5b 108.62(7) . . ?
C5 C6 C7 115.97(11) . . ?
H6a C6 C7 108.29(7) . . ?
H6a C6 C5 108.29(7) . . ?
H6b C6 C7 108.29(7) . . ?
H6b C6 C5 108.29(7) . . ?
H6b C6 H6a 107.4 . . ?
H20a C20 O2 109.5 . . ?
H20b C20 O2 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 O2 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H18a C18 O3 109.5 . . ?
H18b C18 O3 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 O3 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.879
####################################################################### 
# 
# 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_17723_mme-6
_database_code_depnum_ccdc_archive 'CCDC 2085048'
loop_
_audit_author_name
_audit_author_address
'Mariya Kryukova'
;SPbSU
Russia
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_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 H25 Cl2 N O6'
_chemical_formula_sum            'C22 H25 Cl2 N O6'
_chemical_formula_weight         470.33
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0854(3)
_cell_length_b                   7.50448(14)
_cell_length_c                   22.3639(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.532(2)
_cell_angle_gamma                90
_cell_volume                     2193.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11447
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.4200
_cell_measurement_theta_min      3.9490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25659
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21013
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.841
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  10.00   0.50    0.63    --  -47.20  22.00 -81.00   64
  2  ω    -67.00 -41.00   0.50    2.53    -- -106.00  61.00   0.00   52
  3  ω    -98.00 -43.00   0.50    2.53    -- -106.00  77.00  30.00  110
  4  ω    -71.00 -40.00   0.50    2.53    -- -106.00  61.00  90.00   62
  5  ω    -71.00 -40.00   0.50    2.53    -- -106.00  61.00 120.00   62
  6  ω    -94.00 -60.00   0.50    2.53    -- -106.00  77.00  60.00   68
  7  ω    -99.00 -61.00   0.50    2.53    -- -106.00  77.00  90.00   76
  8  ω    -79.00 -54.00   0.50    0.63    --  -47.20 -22.00 113.00   50
  9  ω    -25.00  19.00   0.50    0.63    --   47.20 -22.00 113.00   88
 10  ω     -7.00  62.00   0.50    0.63    --   47.20 -57.00  90.00  138
 11  ω     36.00  69.00   0.50    2.53    --  107.75 -61.00   0.00   66
 12  ω     65.00  93.00   0.50    2.53    --  107.75 -94.00   0.00   56
 13  ω     83.00 112.00   0.50    2.53    --  107.75-125.00   0.00   58
 14  ω     44.00  70.00   0.50    2.53    --  107.75-125.00 -90.00   52
 15  ω     38.00  85.00   0.50    2.53    --  107.75 -77.00 -90.00   94
 16  ω     37.00  71.00   0.50    2.53    --  107.75 -61.00-150.00   68
 17  ω     37.00  69.00   0.50    2.53    --  107.75 -61.00 -90.00   64
 18  ω     39.00  78.00   0.50    2.53    --  107.75-125.00   0.00   78
 19  ω     38.00 118.00   0.50    0.63    --   47.20  22.00 -81.00  160
 20  ω     96.00 135.00   0.50    2.53    --  107.75  22.00 -81.00   78
 21  ω    124.00 175.00   0.50    2.53    --  107.75  45.00   0.00  102
 22  ω    147.00 178.00   0.50    2.53    --  107.75  77.00 -30.00   62
 23  ω    103.00 172.00   0.50    2.53    --  107.75  45.00 -30.00  138
 24  ω     86.00 135.00   0.50    2.53    --  107.75  77.00 -30.00   98
 25  ω    -26.00  25.00   0.50    0.63    --   47.20 -19.00 -30.00  102
 26  ω    -64.00 -34.00   0.50    2.53    -- -106.00  61.00 -90.00   60
 27  ω    -63.00 -37.00   0.50    2.53    -- -106.00  61.00-120.00   52
 28  ω    -71.00 -36.00   0.50    2.53    -- -106.00  61.00-180.00   70
 29  ω   -171.00 -95.00   0.50    2.53    -- -106.00 -22.00 113.00  152
 30  ω   -176.00 -99.00   0.50    2.53    -- -106.00 -45.00  30.00  154
 31  ω    -24.00   1.00   0.50    0.63    --   47.20 -22.00 113.00   50
 32  ω     26.00  53.00   0.50    0.63    --   47.20  77.00 -30.00   54
 33  ω     73.00 108.00   0.50    0.63    --   47.20  37.00 -30.00   70
 34  ω     74.00  99.00   0.50    0.63    --   47.20 125.00-180.00   50
 35  ω     29.00  57.00   0.50    0.63    --   47.20  77.00  90.00   56
 36  ω     40.00  67.00   0.50    0.63    --   47.20  77.00   0.00   54
 37  ω     38.00  65.00   0.50    0.63    --   47.20  37.00 -30.00   54
 38  ω     25.00  69.00   0.50    0.63    --   47.20  77.00  30.00   88
 39  ω     52.00  93.00   0.50    0.63    --   47.20  37.00  30.00   82
 40  ω   -123.00 -88.00   0.50    2.53    -- -106.00 -66.00 -26.42   70
 41  ω   -115.00-107.50   0.50    2.53    -- -106.00 -63.00 -13.18   15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319314000
_diffrn_orient_matrix_UB_12      -0.0567065000
_diffrn_orient_matrix_UB_13      0.0643404000
_diffrn_orient_matrix_UB_21      -0.1134349000
_diffrn_orient_matrix_UB_22      -0.0166777000
_diffrn_orient_matrix_UB_23      0.0149239000
_diffrn_orient_matrix_UB_31      0.0003743000
_diffrn_orient_matrix_UB_32      -0.1965924000
_diffrn_orient_matrix_UB_33      -0.0198010000
_diffrn_oxdiff_digest_frames     
;
0127f9cfa3ba027cbfd235253afde23dce000284cef
;
_diffrn_oxdiff_digest_hkl        
;
0191ba616bd7e0766f4a7f92dcff203710f93e
;
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3811
_reflns_number_total             4140
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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         0.346
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.044
_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)+(0.0439P)²+0.7992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0805
_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:
 C8(H8), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C3(H3), C20(H20), C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.17361(2) 0.94899(5) 0.35078(2) 0.02373(10) Uani 1 1 d . . . . .
Cl2 Cl -0.13096(3) 0.74583(5) 0.45951(2) 0.02633(10) Uani 1 1 d . . . . .
O4 O 0.27720(8) 0.77002(13) 0.48721(4) 0.0216(2) Uani 1 1 d . . . . .
O6 O 0.48347(7) 0.73741(13) 0.44932(4) 0.0221(2) Uani 1 1 d . . . . .
O1 O 0.32082(7) 0.74537(12) 0.28460(4) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.73538(7) 0.34709(13) 0.31235(4) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.46533(8) 0.98756(13) 0.39465(5) 0.0259(2) Uani 1 1 d . . . . .
O3 O 0.25580(9) 0.50854(13) 0.43946(4) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.34634(8) 0.63654(15) 0.33802(5) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.25507(10) 0.89636(17) 0.36279(6) 0.0156(3) Uani 1 1 d . . . . .
C19 C 0.64222(10) 0.42896(18) 0.31765(6) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.28454(10) 0.65990(18) 0.44060(6) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.52381(10) 0.67183(18) 0.30465(6) 0.0178(3) Uani 1 1 d . . . . .
H21 H 0.5091 0.7871 0.2917 0.021 Uiso 1 1 calc R . . . .
C14 C 0.43353(10) 0.84767(18) 0.41136(6) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.33166(10) 0.76228(17) 0.38922(6) 0.0151(3) Uani 1 1 d . . . . .
C16 C 0.44829(10) 0.56988(18) 0.33029(6) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.22448(10) 1.04414(17) 0.38903(6) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.2527 1.0720 0.4268 0.021 Uiso 1 1 calc R . . . .
C20 C 0.62124(10) 0.60177(18) 0.29840(6) 0.0181(3) Uani 1 1 d . . . . .
H20 H 0.6718 0.6699 0.2815 0.022 Uiso 1 1 calc R . . . .
C18 C 0.56677(11) 0.32654(18) 0.34305(6) 0.0193(3) Uani 1 1 d . . . . .
H18 H 0.5814 0.2112 0.3559 0.023 Uiso 1 1 calc R . . . .
C8 C 0.01883(10) 0.79070(18) 0.37448(6) 0.0178(3) Uani 1 1 d . . . . .
H8 H 0.0474 0.6872 0.3961 0.021 Uiso 1 1 calc R . . . .
C17 C 0.46970(10) 0.39674(18) 0.34911(6) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.4190 0.3281 0.3657 0.022 Uiso 1 1 calc R . . . .
C6 C 0.02014(10) 0.96217(18) 0.41166(6) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.0493 0.9465 0.4524 0.023 Uiso 1 1 calc R . . . .
C10 C 0.13690(10) 0.70730(18) 0.29162(6) 0.0183(3) Uani 1 1 d . . . . .
H10A H 0.1501 0.6025 0.3162 0.022 Uiso 1 1 calc R . . . .
H10B H 0.1320 0.6686 0.2502 0.022 Uiso 1 1 calc R . . . .
C11 C 0.22825(10) 0.83371(18) 0.29970(6) 0.0163(3) Uani 1 1 d . . . . .
H11 H 0.2173 0.9375 0.2736 0.020 Uiso 1 1 calc R . . . .
C9 C 0.03353(10) 0.78580(18) 0.30764(6) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.0280 0.9060 0.2919 0.022 Uiso 1 1 calc R . . . .
H9B H -0.0208 0.7154 0.2885 0.022 Uiso 1 1 calc R . . . .
C4 C 0.14661(11) 1.16893(18) 0.36100(6) 0.0196(3) Uani 1 1 d . . . . .
H4A H 0.1424 1.1491 0.3181 0.024 Uiso 1 1 calc R . . . .
H4B H 0.1691 1.2907 0.3679 0.024 Uiso 1 1 calc R . . . .
C5 C 0.03876(11) 1.14501(18) 0.38601(6) 0.0210(3) Uani 1 1 d . . . . .
H5A H 0.0296 1.2333 0.4170 0.025 Uiso 1 1 calc R . . . .
H5B H -0.0122 1.1677 0.3541 0.025 Uiso 1 1 calc R . . . .
C7 C -0.07760(11) 0.86153(19) 0.39976(6) 0.0202(3) Uani 1 1 d . . . . .
C22 C 0.81982(11) 0.46047(19) 0.30077(7) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.8104 0.5113 0.2615 0.033 Uiso 1 1 calc GR . . . .
H22B H 0.8819 0.3923 0.3030 0.033 Uiso 1 1 calc GR . . . .
H22C H 0.8239 0.5541 0.3300 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.23119(14) 0.6950(2) 0.53901(6) 0.0296(3) Uani 1 1 d . . . . .
H13A H 0.1617 0.6621 0.5288 0.044 Uiso 1 1 calc GR . . . .
H13B H 0.2323 0.7816 0.5706 0.044 Uiso 1 1 calc GR . . . .
H13C H 0.2689 0.5913 0.5521 0.044 Uiso 1 1 calc GR . . . .
C15 C 0.58725(12) 0.7894(2) 0.46679(8) 0.0322(4) Uani 1 1 d . . . . .
H15A H 0.6288 0.7853 0.4325 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.6144 0.7091 0.4969 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.5872 0.9084 0.4826 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 C7 1.7571(14) . ?
Cl2 C7 1.7635(14) . ?
O4 C12 1.3369(16) . ?
O4 C13 1.4434(17) . ?
O6 C14 1.3354(17) . ?
O6 C15 1.4500(18) . ?
O1 N1 1.4732(14) . ?
O1 C11 1.4342(16) . ?
O2 C19 1.3749(16) . ?
O2 C22 1.4272(17) . ?
O5 C14 1.1953(17) . ?
O3 C12 1.1964(17) . ?
N1 C1 1.5026(16) . ?
N1 C16 1.4424(17) . ?
C2 C1 1.5211(18) . ?
C2 C3 1.3249(19) . ?
C2 C11 1.5136(18) . ?
C19 C20 1.390(2) . ?
C19 C18 1.392(2) . ?
C12 C1 1.5342(18) . ?
C21 H21 0.9300 . ?
C21 C16 1.3932(19) . ?
C21 C20 1.3918(19) . ?
C14 C1 1.5410(18) . ?
C16 C17 1.3905(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.5006(19) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.387(2) . ?
C8 H8 0.9800 . ?
C8 C6 1.5317(19) . ?
C8 C9 1.5161(18) . ?
C8 C7 1.5024(19) . ?
C17 H17 0.9300 . ?
C6 H6 0.9800 . ?
C6 C5 1.511(2) . ?
C6 C7 1.4989(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5305(19) . ?
C10 C9 1.5323(19) . ?
C11 H11 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.551(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C12 O4 C13 115.56(11) . . ?
C14 O6 C15 115.50(12) . . ?
C11 O1 N1 103.23(9) . . ?
C19 O2 C22 116.47(11) . . ?
O1 N1 C1 103.75(9) . . ?
C16 N1 O1 105.83(9) . . ?
C16 N1 C1 117.34(10) . . ?
C3 C2 C1 126.04(12) . . ?
C3 C2 C11 127.64(12) . . ?
C11 C2 C1 106.16(11) . . ?
O2 C19 C20 123.64(12) . . ?
O2 C19 C18 115.85(12) . . ?
C20 C19 C18 120.50(12) . . ?
O4 C12 C1 108.63(11) . . ?
O3 C12 O4 124.76(12) . . ?
O3 C12 C1 126.57(12) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C16 120.23(12) . . ?
O6 C14 C1 109.80(11) . . ?
O5 C14 O6 125.15(12) . . ?
O5 C14 C1 124.95(12) . . ?
N1 C1 C2 102.92(10) . . ?
N1 C1 C12 108.99(10) . . ?
N1 C1 C14 111.60(10) . . ?
C2 C1 C12 110.04(11) . . ?
C2 C1 C14 113.30(11) . . ?
C12 C1 C14 109.76(10) . . ?
C21 C16 N1 122.38(12) . . ?
C17 C16 N1 117.57(12) . . ?
C17 C16 C21 120.05(12) . . ?
C2 C3 H3 118.3 . . ?
C2 C3 C4 123.38(12) . . ?
C4 C3 H3 118.3 . . ?
C19 C20 C21 119.38(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 119.95(12) . . ?
C17 C18 H18 120.0 . . ?
C6 C8 H8 113.8 . . ?
C9 C8 H8 113.8 . . ?
C9 C8 C6 123.83(12) . . ?
C7 C8 H8 113.8 . . ?
C7 C8 C6 59.20(9) . . ?
C7 C8 C9 121.66(11) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.89(12) . . ?
C18 C17 H17 120.1 . . ?
C8 C6 H6 113.5 . . ?
C5 C6 C8 123.70(11) . . ?
C5 C6 H6 113.5 . . ?
C7 C6 C8 59.43(9) . . ?
C7 C6 H6 113.5 . . ?
C7 C6 C5 122.73(12) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C11 C10 C9 115.28(11) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
O1 C11 C2 101.51(10) . . ?
O1 C11 C10 110.43(10) . . ?
O1 C11 H11 109.3 . . ?
C2 C11 C10 116.77(11) . . ?
C2 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C8 C9 C10 113.06(11) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.89(11) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C5 C4 113.98(11) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
Cl1 C7 Cl2 111.11(8) . . ?
C8 C7 Cl1 119.14(10) . . ?
C8 C7 Cl2 118.57(10) . . ?
C6 C7 Cl1 120.23(10) . . ?
C6 C7 Cl2 118.48(10) . . ?
C6 C7 C8 61.37(9) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C12 C1 N1 176.46(10) . . . . ?
O4 C12 C1 C2 -71.38(13) . . . . ?
O4 C12 C1 C14 53.96(14) . . . . ?
O6 C14 C1 N1 -83.11(13) . . . . ?
O6 C14 C1 C2 161.27(11) . . . . ?
O6 C14 C1 C12 37.83(14) . . . . ?
O1 N1 C1 C2 25.18(12) . . . . ?
O1 N1 C1 C12 141.97(10) . . . . ?
O1 N1 C1 C14 -96.64(11) . . . . ?
O1 N1 C16 C21 37.47(15) . . . . ?
O1 N1 C16 C17 -142.07(11) . . . . ?
O2 C19 C20 C21 178.74(12) . . . . ?
O2 C19 C18 C17 -178.72(12) . . . . ?
O5 C14 C1 N1 93.34(15) . . . . ?
O5 C14 C1 C2 -22.27(19) . . . . ?
O5 C14 C1 C12 -145.72(13) . . . . ?
O3 C12 C1 N1 -5.64(18) . . . . ?
O3 C12 C1 C2 106.51(15) . . . . ?
O3 C12 C1 C14 -128.15(14) . . . . ?
N1 O1 C11 C2 45.86(11) . . . . ?
N1 O1 C11 C10 -78.63(11) . . . . ?
N1 C16 C17 C18 -179.59(11) . . . . ?
C2 C3 C4 C5 100.96(15) . . . . ?
C19 C18 C17 C16 -0.6(2) . . . . ?
C21 C16 C17 C18 0.86(19) . . . . ?
C1 N1 C16 C21 -77.67(15) . . . . ?
C1 N1 C16 C17 102.79(13) . . . . ?
C1 C2 C3 C4 -178.52(12) . . . . ?
C1 C2 C11 O1 -29.56(12) . . . . ?
C1 C2 C11 C10 90.55(13) . . . . ?
C16 N1 C1 C2 141.46(11) . . . . ?
C16 N1 C1 C12 -101.75(12) . . . . ?
C16 N1 C1 C14 19.63(15) . . . . ?
C16 C21 C20 C19 0.4(2) . . . . ?
C3 C2 C1 N1 -173.45(12) . . . . ?
C3 C2 C1 C12 70.51(16) . . . . ?
C3 C2 C1 C14 -52.78(18) . . . . ?
C3 C2 C11 O1 146.12(13) . . . . ?
C3 C2 C11 C10 -93.77(16) . . . . ?
C3 C4 C5 C6 -24.58(16) . . . . ?
C20 C19 C18 C17 0.2(2) . . . . ?
C20 C21 C16 N1 179.71(11) . . . . ?
C20 C21 C16 C17 -0.8(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C8 C6 C5 C4 -63.81(17) . . . . ?
C8 C6 C7 Cl1 -108.90(12) . . . . ?
C8 C6 C7 Cl2 108.89(12) . . . . ?
C6 C8 C9 C10 108.54(14) . . . . ?
C6 C8 C7 Cl1 110.63(12) . . . . ?
C6 C8 C7 Cl2 -108.75(11) . . . . ?
C11 O1 N1 C1 -45.58(11) . . . . ?
C11 O1 N1 C16 -169.69(10) . . . . ?
C11 C2 C1 N1 2.32(13) . . . . ?
C11 C2 C1 C12 -113.72(11) . . . . ?
C11 C2 C1 C14 122.99(11) . . . . ?
C11 C2 C3 C4 6.6(2) . . . . ?
C11 C10 C9 C8 -78.47(15) . . . . ?
C9 C8 C6 C5 -1.5(2) . . . . ?
C9 C8 C6 C7 109.64(14) . . . . ?
C9 C8 C7 Cl1 -2.56(18) . . . . ?
C9 C8 C7 Cl2 138.06(11) . . . . ?
C9 C8 C7 C6 -113.20(14) . . . . ?
C9 C10 C11 O1 178.84(10) . . . . ?
C9 C10 C11 C2 63.60(15) . . . . ?
C5 C6 C7 Cl1 3.83(18) . . . . ?
C5 C6 C7 Cl2 -138.39(11) . . . . ?
C5 C6 C7 C8 112.73(14) . . . . ?
C7 C8 C6 C5 -111.16(15) . . . . ?
C7 C8 C9 C10 -179.57(12) . . . . ?
C7 C6 C5 C4 -136.47(13) . . . . ?
C22 O2 C19 C20 16.28(18) . . . . ?
C22 O2 C19 C18 -164.83(12) . . . . ?
C13 O4 C12 O3 0.3(2) . . . . ?
C13 O4 C12 C1 178.23(11) . . . . ?
C15 O6 C14 O5 -5.2(2) . . . . ?
C15 O6 C14 C1 171.27(11) . . . . ?

_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 2.239
_oxdiff_exptl_absorpt_empirical_full_min 0.659
####################################################################### 
# 
# 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_13129-maa-2
_database_code_depnum_ccdc_archive 'CCDC 2085047'
loop_
_audit_author_name
_audit_author_address
'Mariya Kryukova'
;SPbSU
Russia
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_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         'C20 H23 N O5'
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H12O5N1
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                   8.32060(10)
_cell_length_b                   10.38740(10)
_cell_length_c                   20.71850(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1790.69(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28991
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.2450
_cell_measurement_theta_min      2.1500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.50a (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_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.406
_diffrn_reflns_theta_min         4.762
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_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    -59.00  25.00   0.50    0.20    --  -38.82  86.00  41.00  168
  2  ω     12.00  44.00   0.50    0.20    --   38.82 -86.00 -76.00   64
  3  ω    120.00 146.00   0.50    0.20    --  100.00  86.00  41.00   52
  4  ω    102.00 128.00   0.50    0.20    --  100.00 -86.00 -76.00   52
  5  ω    -61.00 -18.00   0.50    0.20    --    0.00 142.00 150.06   86
  6  ω    -47.00 -22.00   0.50    0.20    --   24.00 158.00-106.07   50
  7  ω    -42.00 -17.00   0.50    0.20    --   24.00 149.00  64.13   50
  8  ω     -7.00  18.00   0.50    0.20    --   28.00  98.00-107.08   50
  9  ω      0.00  25.00   0.50    0.20    --   32.00  90.00 149.36   50
 10  ω      0.00  25.00   0.50    0.20    --   32.00  91.00  -0.47   50
 11  ω     -1.00  24.00   0.50    0.20    --   32.00  93.00-161.37   50
 12  ω     -1.00  24.00   0.50    0.20    --   32.00  94.00  31.45   50
 13  ω      6.00  31.00   0.50    0.20    --   36.00  87.00 139.17   50
 14  ω      5.00  30.00   0.50    0.20    --   36.00  89.00-157.69   50
 15  ω      6.00  31.00   0.50    0.20    --   36.00  86.00 173.24   50
 16  ω      4.00  29.00   0.50    0.20    --   36.00  90.00 -41.93   50
 17  ω      4.00  29.00   0.50    0.20    --   36.00  90.00  69.13   50
 18  ω      6.00  31.00   0.50    0.20    --   36.00  88.00-127.81   50
 19  ω    -88.00 -32.00   0.50    0.20    --  -38.82 138.00 -60.00  112
 20  ω    -62.00  24.00   0.50    0.20    --  -38.82  65.00 -90.00  172
 21  ω     17.00  85.00   0.50    0.20    --   38.82-138.00  30.00  136
 22  ω      9.00  34.00   0.50    0.20    --   38.82  85.00  88.79   50
 23  ω    -27.00  66.00   0.50    0.20    --   38.82 -77.00  90.00  186
 24  ω     38.00  93.00   0.50    0.20    --   38.82-138.00-120.00  110
 25  ω     26.00  75.00   0.50    0.20    --   38.82-104.00-180.00   98
 26  ω     11.00  36.00   0.50    0.20    --   40.00  84.00-179.77   50
 27  ω     11.00  36.00   0.50    0.20    --   40.00  84.00-161.47   50
 28  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 103.90   50
 29  ω     16.00  41.00   0.50    0.20    --   44.00  81.00   5.99   50
 30  ω     17.00  42.00   0.50    0.20    --   44.00  79.00 -85.50   50
 31  ω     16.00  41.00   0.50    0.20    --   44.00  82.00-149.94   50
 32  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 -72.60   50
 33  ω     16.00  41.00   0.50    0.20    --   44.00  81.00-174.73   50
 34  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 -19.20   50
 35  ω     16.00  41.00   0.50    0.20    --   44.00  82.00  41.48   50
 36  ω     20.00  45.00   0.50    0.20    --   44.00  80.00-130.48   50
 37  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 141.06   50
 38  ω     19.00  45.00   0.50    0.20    --   44.00  80.00  21.66   52
 39  ω     17.00  42.00   0.50    0.20    --   44.00  79.00  97.53   50
 40  ω     16.00  41.00   0.50    0.20    --   44.00  81.00  56.88   50
 41  ω     27.00  70.00   0.50    0.20    --   52.00  75.00 -47.79   86
 42  ω     31.00  57.00   0.50    0.20    --   56.00  76.00 151.27   52
 43  ω     29.00  64.00   0.50    0.20    --   56.00  77.00-152.42   70
 44  ω     90.00 124.00   0.50    0.20    --   60.00  76.00 -15.27   68
 45  ω     74.00 125.00   0.50    0.20    --   60.00  77.00 171.94  102
 46  ω     88.00 125.00   0.50    0.20    --   60.00  73.00  70.21   74
 47  ω     90.00 117.00   0.50    0.20    --   60.00  75.00-139.32   54
 48  ω     35.00  68.00   0.50    0.20    --   60.00  75.00-139.32   66
 49  ω     35.00  61.00   0.50    0.20    --   60.00  73.00  70.21   52
 50  ω     34.00  66.00   0.50    0.20    --   60.00  76.00 -15.27   64
 51  ω     33.00  64.00   0.50    0.20    --   60.00  77.00 171.94   62
 52  ω     38.00 119.00   0.50    0.20    --   64.00  76.00  24.46  162
 53  ω     37.00  73.00   0.50    0.20    --   64.00  77.00  88.74   72
 54  ω     98.00 124.00   0.50    0.20    --   64.00  77.00  88.74   52
 55  ω     91.00 119.00   0.50    0.20    --   64.00  70.00 130.22   56
 56  ω     39.00  76.00   0.50    0.20    --   64.00  70.00 130.22   74
 57  ω     40.00  76.00   0.50    0.20    --   64.00  73.00 -98.51   72
 58  ω     86.00 124.00   0.50    0.20    --   64.00  73.00 -98.51   76
 59  ω     42.00  70.00   0.50    0.20    --   68.00  77.00-129.57   56
 60  ω     98.00 124.00   0.50    0.20    --   68.00  77.00-129.57   52
 61  ω     47.00  97.00   0.50    0.20    --   68.00  66.00-140.03  100
 62  ω     46.00 113.00   0.50    0.20    --   68.00  63.00 -61.78  134
 63  ω     45.00 132.00   0.50    0.20    --   68.00  65.00 -24.06  174
 64  ω     45.00  78.00   0.50    0.20    --   68.00  64.00  67.33   66
 65  ω     47.00  77.00   0.50    0.20    --   72.00  75.00  90.39   60
 66  ω     55.00  81.00   0.50    0.20    --   72.00  56.00  27.39   52
 67  ω    111.00 138.00   0.50    0.20    --   72.00  75.00  90.39   54
 68  ω     51.00 141.00   0.50    0.20    --   76.00  72.00 -59.18  180
 69  ω     52.00  98.00   0.50    0.20    --   76.00  73.00-131.45   92
 70  ω     56.00 112.00   0.50    0.20    --   76.00  55.00-166.71  112
 71  ω    104.00 130.00   0.50    0.20    --   76.00  66.00 -82.83   52
 72  ω     59.00 100.00   0.50    0.20    --   76.00  66.00 -82.83   82
 73  ω     59.00  85.00   0.50    0.20    --   80.00  62.00 106.37   52
 74  ω     58.00  92.00   0.50    0.20    --   80.00  59.00   0.68   68
 75  ω     60.00  98.00   0.50    0.20    --   84.00  68.00-104.24   76
 76  ω     59.00  97.00   0.50    0.20    --   84.00  70.00 115.43   76
 77  ω    103.00 150.00   0.50    0.20    --   84.00  70.00 115.43   94
 78  ω     67.00  92.00   0.50    0.20    --   88.00  62.00 157.14   50
 79  ω    132.00 157.00   0.50    0.20    --   96.00  74.00 -62.97   50
 80  ω     70.00 100.00   0.50    0.20    --   96.00  74.00 -62.97   60
 81  ω     73.00 112.00   0.50    0.20    --  100.00  77.00 120.00   78
 82  ω     65.00 112.00   0.50    0.20    --  100.00 -53.00 -60.00   94
 83  ω     36.00 109.00   0.50    0.20    --  100.00-133.00   0.00  146
 84  ω    121.00 150.00   0.50    0.20    --  100.00  77.00 -41.69   58
 85  ω     73.00 113.00   0.50    0.20    --  100.00  77.00 -41.69   80
 86  ω     78.00 151.00   0.50    0.20    --  100.00  61.00-120.00  146
 87  ω     73.00 152.00   0.50    0.20    --  100.00  77.00  30.00  158
 88  ω     93.00 118.00   0.50    0.20    --  100.00 -45.00 -90.00   50
 89  ω     76.00 102.00   0.50    0.20    --  100.00  69.00  60.00   52
 90  ω     76.00 102.00   0.50    0.20    --  100.00  69.00-120.00   52
 91  ω    111.00 157.00   0.50    0.20    --  100.00  77.00-180.00   92
 92  ω     73.00 106.00   0.50    0.20    --  100.00  77.00-180.00   66
 93  ω     36.00  85.00   0.50    0.20    --  100.00 -45.00 -90.00   98
 94  ω     73.00 114.00   0.50    0.20    --  100.00  77.00 150.00   82
 95  ω     82.00 108.00   0.50    0.20    --  100.00 -93.00 150.00   52
 96  ω     27.00  52.00   0.50    0.20    --  100.00 -93.00 150.00   50
 97  ω     89.00 145.00   0.50    0.20    --  100.00  37.00 -30.00  112
 98  ω     68.00 114.00   0.50    0.20    --  100.00 -30.00 -90.00   92
 99  ω     69.00 123.00   0.50    0.20    --  100.00-133.00 -60.00  108
100  ω     73.00 117.00   0.50    0.20    --  100.00  77.00   0.00   88
101  ω     53.00 108.00   0.50    0.20    --  100.00 -93.00 -30.00  110
102  ω     32.00 108.00   0.50    0.20    --  100.00-111.00  90.00  152
103  ω     73.00 157.00   0.50    0.20    --  100.00  77.00  60.00  168
104  ω     76.00 131.00   0.50    0.20    --  100.00  69.00-180.00  110
105  ω     87.00 126.00   0.50    0.20    --  100.00 -86.00-150.00   78
106  ω     81.00 106.00   0.50    0.20    --  100.00 -45.00  60.00   50
107  ω     38.00 101.00   0.50    0.20    --  100.00 -61.00  90.00  126
108  ω     50.00  79.00   0.50    0.20    --  100.00 -86.00-150.00   58
109  ω     62.00 130.00   0.50    0.20    --  100.00 -15.00   0.00  136
110  ω     79.00 125.00   0.50    0.20    --  100.00  61.00  30.00   92
111  ω     88.00 155.00   0.50    0.20    --  100.00  37.00 -60.00  134
112  ω     76.00 101.00   0.50    0.20    --  100.00  69.00 -90.00   50
113  ω    124.00 150.00   0.50    0.20    --  100.00  77.00-120.00   52
114  ω     78.00 104.00   0.50    0.20    --  100.00  77.00-120.00   52
115  ω     36.00  62.00   0.50    0.20    --  100.00 -45.00  60.00   52
116  ω    113.00 150.00   0.50    0.20    --  100.00  45.00-180.00   74
117  ω    132.00 157.00   0.50    0.20    --  100.00  77.00 -90.00   50
118  ω     78.00 121.00   0.50    0.20    --  100.00  61.00  60.00   86
119  ω     73.00 106.00   0.50    0.20    --  100.00  77.00 -90.00   66
120  ω     78.00 152.00   0.50    0.20    --  100.00  61.00   0.00  148
121  ω     44.00  70.00   0.50    0.20    --  100.00-133.00-150.00   52
122  ω     98.00 123.00   0.50    0.20    --  100.00-133.00-150.00   50
123  ω    100.00 157.00   0.50    0.20    --  100.00  53.00 120.00  114
124  ω    123.00 156.00   0.50    0.20    --  100.00  77.00-150.00   66
125  ω     75.00 101.00   0.50    0.20    --  100.00  77.00-150.00   52
126  ω    106.00 156.00   0.50    0.20    --  100.00  77.00 -30.00  100
127  ω     43.00 114.00   0.50    0.20    --  100.00 -30.00 120.00  142
128  ω     74.00 134.00   0.50    0.20    --  100.00  76.00-158.92  120
129  ω     74.00 109.00   0.50    0.20    --  100.00  77.00  90.00   70
130  ω     77.00 123.00   0.50    0.20    --  100.00 178.00   0.00   92
131  ω     64.00 112.00   0.50    0.20    --  100.00 -37.00 150.00   96
132  ω     74.00 100.00   0.50    0.20    --  100.00  77.00 -60.00   52
133  ω     73.00  99.00   0.50    0.20    --  100.00  77.00 -30.00   52
134  ω     86.00 111.00   0.50    0.20    --  100.00-111.00   0.00   50
135  ω     34.00  60.00   0.50    0.20    --  100.00-111.00   0.00   52
136  ω     79.00 140.00   0.50    0.20    --  100.00  61.00 150.00  122
137  ω    115.00 149.00   0.50    0.20    --  100.00  61.00  90.00   68
138  ω     36.00 114.00   0.50    0.20    --  100.00 -53.00 120.00  156
139  ω     80.00 107.00   0.50    0.20    --  100.00  61.00  90.00   54
140  ω     91.00 143.00   0.50    0.20    --  100.00  93.00   0.00  104
141  ω    119.00 155.00   0.50    0.20    --  100.00  30.00 150.00   72
142  ω     25.00  82.00   0.50    0.20    --  100.00 -15.00 -60.00  114
143  ω    129.00 154.00   0.50    0.20    --  100.00  77.00 120.00   50
144  ω     38.00  64.00   0.50    0.20    --  100.00 -69.00 -90.00   52
145  ω     84.00 115.00   0.50    0.20    --  100.00 -69.00 -90.00   62
146  ω    108.00 154.00   0.50    0.20    --  100.00  93.00  60.00   92
147  ω     31.00 126.00   0.50    0.20    --  100.00 -86.00  90.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0710210000
_diffrn_orient_matrix_UB_12      -0.0527190000
_diffrn_orient_matrix_UB_13      0.0633638000
_diffrn_orient_matrix_UB_21      -0.0471987000
_diffrn_orient_matrix_UB_22      -0.1376130000
_diffrn_orient_matrix_UB_23      -0.0202495000
_diffrn_orient_matrix_UB_31      0.1643344000
_diffrn_orient_matrix_UB_32      -0.0166801000
_diffrn_orient_matrix_UB_33      -0.0332376000
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3366
_reflns_number_total             3424
_reflns_odcompleteness_completeness 96.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.50a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.50a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.028
_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)+(0.0657P)²+0.2958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(2)
 0.4(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C4(H4A,H4B), C9(H9A,H9B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C6(H6), C16(H16), C10(H10), C17(H17), C18(H18), C7(H7)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_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 0.64806(17) 0.29802(13) 0.46646(6) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.27718(17) 0.49666(13) 0.49912(6) 0.0183(3) Uani 1 1 d . . . . .
O4 O 0.59160(18) 0.68447(13) 0.39364(6) 0.0202(3) Uani 1 1 d . . . . .
O3 O 0.39686(18) 0.68964(13) 0.51067(7) 0.0201(3) Uani 1 1 d . . . . .
O5 O 0.79054(18) 0.54237(13) 0.41193(7) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.5184(2) 0.38080(14) 0.44570(7) 0.0140(3) Uani 1 1 d . . . . .
C13 C 0.3998(2) 0.57771(18) 0.49472(9) 0.0147(4) Uani 1 1 d . . . . .
C15 C 0.4857(2) 0.36504(18) 0.37934(9) 0.0156(4) Uani 1 1 d . . . . .
C2 C 0.6542(2) 0.47986(18) 0.53107(8) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.6459(2) 0.59321(18) 0.42184(9) 0.0153(4) Uani 1 1 d . . . . .
C19 C 0.3373(3) 0.4324(2) 0.28493(9) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.2680 0.4904 0.2650 0.026 Uiso 1 1 calc R . . . .
C20 C 0.3805(3) 0.45083(18) 0.34922(9) 0.0177(4) Uani 1 1 d . . . . .
H20 H 0.3393 0.5204 0.3721 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4722(3) 0.4158(2) 0.66872(9) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.3607 0.4099 0.6672 0.027 Uiso 1 1 calc R . . . .
C3 C 0.6702(3) 0.33440(18) 0.53341(9) 0.0162(4) Uani 1 1 d . . . . .
H3 H 0.7793 0.3116 0.5471 0.019 Uiso 1 1 calc R . . . .
C1 C 0.5533(2) 0.51074(17) 0.47130(8) 0.0139(4) Uani 1 1 d . . . . .
C16 C 0.5462(3) 0.26055(19) 0.34468(10) 0.0201(4) Uani 1 1 d . . . . .
H16 H 0.6167 0.2029 0.3641 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7144(2) 0.56854(18) 0.56997(9) 0.0168(4) Uani 1 1 d . . . . .
H10 H 0.6989 0.6542 0.5586 0.020 Uiso 1 1 calc R . . . .
C17 C 0.4995(3) 0.2435(2) 0.28028(10) 0.0253(5) Uani 1 1 d . . . . .
H17 H 0.5390 0.1734 0.2573 0.030 Uiso 1 1 calc R . . . .
C8 C 0.7042(3) 0.5707(2) 0.69162(10) 0.0240(5) Uani 1 1 d . . . . .
H8A H 0.7543 0.5285 0.7282 0.029 Uiso 1 1 calc R . . . .
H8B H 0.7069 0.6627 0.6997 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3966(3) 0.3282(2) 0.25031(10) 0.0245(5) Uani 1 1 d . . . . .
H18 H 0.3671 0.3159 0.2075 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5484(3) 0.26417(18) 0.57614(9) 0.0190(4) Uani 1 1 d . . . . .
H4A H 0.5629 0.1722 0.5707 0.023 Uiso 1 1 calc R . . . .
H4B H 0.4410 0.2855 0.5615 0.023 Uiso 1 1 calc R . . . .
C7 C 0.5299(3) 0.5283(2) 0.68822(9) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.4542 0.5886 0.7014 0.026 Uiso 1 1 calc R . . . .
C14 C 0.1335(3) 0.5481(2) 0.52906(11) 0.0254(5) Uani 1 1 d . . . . .
H14A H 0.0925 0.6177 0.5034 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.1590 0.5791 0.5715 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.0538 0.4816 0.5321 0.038 Uiso 1 1 calc GR . . . .
C9 C 0.8054(2) 0.5421(2) 0.63078(9) 0.0200(4) Uani 1 1 d . . . . .
H9A H 0.9017 0.5948 0.6315 0.024 Uiso 1 1 calc R . . . .
H9B H 0.8383 0.4526 0.6313 0.024 Uiso 1 1 calc R . . . .
C5 C 0.5613(3) 0.2965(2) 0.64868(9) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.5205 0.2242 0.6733 0.026 Uiso 1 1 calc R . . . .
H5B H 0.6739 0.3070 0.6596 0.026 Uiso 1 1 calc R . . . .
C12 C 0.8873(3) 0.6061(2) 0.36365(10) 0.0264(5) Uani 1 1 d . . . . .
H12A H 0.8276 0.6124 0.3241 0.040 Uiso 1 1 calc GR . . . .
H12B H 0.9837 0.5574 0.3563 0.040 Uiso 1 1 calc GR . . . .
H12C H 0.9149 0.6909 0.3784 0.040 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 N1 1.445(2) . ?
O1 C3 1.449(2) . ?
O2 C13 1.326(2) . ?
O2 C14 1.449(2) . ?
O4 C11 1.202(2) . ?
O3 C13 1.209(2) . ?
O5 C11 1.330(3) . ?
O5 C12 1.445(2) . ?
N1 C15 1.411(2) . ?
N1 C1 1.479(2) . ?
C13 C1 1.533(3) . ?
C15 C20 1.396(3) . ?
C15 C16 1.395(3) . ?
C2 C3 1.518(2) . ?
C2 C1 1.530(2) . ?
C2 C10 1.323(3) . ?
C11 C1 1.542(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(3) . ?
C19 C18 1.389(3) . ?
C20 H20 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.327(3) . ?
C6 C5 1.503(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.531(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.401(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.495(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.517(3) . ?
C8 C9 1.545(3) . ?
C18 H18 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.544(3) . ?
C7 H7 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
N1 O1 C3 102.98(13) . . ?
C13 O2 C14 115.47(14) . . ?
C11 O5 C12 115.41(16) . . ?
O1 N1 C1 106.86(13) . . ?
C15 N1 O1 111.42(14) . . ?
C15 N1 C1 119.54(14) . . ?
O2 C13 C1 112.00(15) . . ?
O3 C13 O2 125.20(18) . . ?
O3 C13 C1 122.66(17) . . ?
C20 C15 N1 118.85(17) . . ?
C16 C15 N1 121.45(18) . . ?
C16 C15 C20 119.52(17) . . ?
C3 C2 C1 106.43(15) . . ?
C10 C2 C3 129.84(18) . . ?
C10 C2 C1 123.72(17) . . ?
O4 C11 O5 125.32(18) . . ?
O4 C11 C1 125.00(18) . . ?
O5 C11 C1 109.52(16) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.09(19) . . ?
C19 C20 H20 120.0 . . ?
C7 C6 H6 115.4 . . ?
C7 C6 C5 129.2(2) . . ?
C5 C6 H6 115.4 . . ?
O1 C3 C2 102.58(14) . . ?
O1 C3 H3 109.3 . . ?
O1 C3 C4 110.19(16) . . ?
C2 C3 H3 109.3 . . ?
C2 C3 C4 115.77(17) . . ?
C4 C3 H3 109.3 . . ?
N1 C1 C13 111.36(15) . . ?
N1 C1 C2 101.91(14) . . ?
N1 C1 C11 111.52(14) . . ?
C13 C1 C11 112.00(15) . . ?
C2 C1 C13 107.21(14) . . ?
C2 C1 C11 112.35(16) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.25(19) . . ?
C17 C16 H16 120.4 . . ?
C2 C10 H10 117.4 . . ?
C2 C10 C9 125.28(18) . . ?
C9 C10 H10 117.4 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.40(19) . . ?
C18 C17 H17 119.3 . . ?
H8A C8 H8B 107.5 . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C7 C8 C9 115.31(17) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.12(19) . . ?
C17 C18 H18 120.4 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.41(17) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C6 C7 C8 128.0(2) . . ?
C6 C7 H7 116.0 . . ?
C8 C7 H7 116.0 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C8 112.10(17) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C6 C5 C4 114.46(17) . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 203.197
_oxdiff_exptl_absorpt_empirical_full_min 0.413
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(2)
2 0.4(2)

####################################################################### 
# 
# 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_16022_apm-502
_database_code_depnum_ccdc_archive 'CCDC 2085046'
loop_
_audit_author_name
_audit_author_address
'Mariya Kryukova'
;SPbSU
Russia
;
_audit_update_record             
;
2021-05-21 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-05-19
_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 H25 Cl2 N O6'
_chemical_formula_sum            'C22 H25 Cl2 N O6'
_chemical_formula_weight         470.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H25 Cl2 N O6 '
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9201(3)
_cell_length_b                   27.3837(9)
_cell_length_c                   9.5899(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.369(4)
_cell_angle_gamma                90
_cell_volume                     2209.90(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11999
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.9400
_cell_measurement_theta_min      5.1350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18890
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.385
_diffrn_reflns_theta_min         3.228
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  27.00   0.50    0.66    --  -47.20  19.00-120.00  106
  2  ω     67.00  92.00   0.50    0.66    --   47.20 142.00 -87.00   50
  3  ω     74.00 120.00   0.50    0.66    --   47.20 125.00 -90.00   92
  4  ω     93.00 118.00   0.50    2.63    --  107.75 142.00 -87.00   50
  5  ω    141.00 174.00   0.50    2.63    --  107.75  45.00-150.00   66
  6  ω    108.00 141.00   0.50    2.63    --  107.75  30.00 -90.00   66
  7  ω     99.00 143.00   0.50    2.63    --  107.75  30.00-150.00   88
  8  ω     53.00  98.00   0.50    2.63    --  107.75 -94.00  30.00   90
  9  ω     76.00 103.00   0.50    2.63    --  107.75 -94.00  60.00   54
 10  ω     87.00 112.00   0.50    2.63    --  107.75-125.00  90.00   50
 11  ω     50.00  75.00   0.50    2.63    --  107.75-128.00  26.00   50
 12  ω     35.00  61.00   0.50    2.63    --  107.75 -94.00  60.00   52
 13  ω     49.00  75.00   0.50    2.63    --  107.75 -77.00  90.00   52
 14  ω     35.00  71.00   0.50    2.63    --  107.75 -61.00 150.00   72
 15  ω     43.00  69.00   0.50    2.63    --  107.75-125.00  90.00   52
 16  ω     38.00  71.00   0.50    2.63    --  107.75 -61.00 -90.00   66
 17  ω     70.00 105.00   0.50    2.63    --  107.75 -94.00 -90.00   70
 18  ω     67.00 121.00   0.50    2.63    --  107.75-142.00-144.00  108
 19  ω     39.00  64.00   0.50    2.63    --  107.75-142.00-144.00   50
 20  ω     32.00 111.00   0.50    0.66    --   47.20  57.00-150.00  158
 21  ω    129.00 178.00   0.50    2.63    --  107.75  61.00  90.00   98
 22  ω    144.00 178.00   0.50    2.63    --  107.75  45.00 150.00   68
 23  ω     82.00 152.00   0.50    2.63    --  107.75 128.00 101.00  140
 24  ω    -68.00 -41.00   0.50    0.66    --  -47.20 128.00 101.00   54
 25  ω    -65.00 -40.00   0.50    2.63    -- -106.00  61.00  60.00   50
 26  ω    -70.00 -35.00   0.50    2.63    -- -106.00  61.00  90.00   70
 27  ω    -66.00 -41.00   0.50    2.63    -- -106.00 128.00  39.43   50
 28  ω    -97.00 -72.00   0.50    2.63    -- -106.00 128.00 101.00   50
 29  ω   -113.00 -72.00   0.50    2.63    -- -106.00 128.00  39.43   82
 30  ω   -107.00 -44.00   0.50    2.63    -- -106.00 108.00  74.45  126
 31  ω    -95.00 -62.00   0.50    0.66    --  -47.20 142.00 -87.00   66
 32  ω   -124.00 -89.00   0.50    2.63    -- -106.00 142.00 -87.00   70
 33  ω   -176.00 -89.00   0.50    2.63    -- -106.00 -61.00 -60.00  174
 34  ω   -120.00 -64.00   0.50    0.66    --  -47.20-142.00-144.00  112
 35  ω   -109.00 -84.00   0.50    0.66    --  -47.20-128.00  26.00   50
 36  ω   -112.00 -86.00   0.50    0.66    --  -47.20-125.00  90.00   52
 37  ω     78.00  91.50   0.50    2.63    --  107.75 142.00 -87.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1165386000
_diffrn_orient_matrix_UB_12      0.0245895000
_diffrn_orient_matrix_UB_13      -0.1380428000
_diffrn_orient_matrix_UB_21      0.0637612000
_diffrn_orient_matrix_UB_22      0.0505177000
_diffrn_orient_matrix_UB_23      0.0628566000
_diffrn_orient_matrix_UB_31      0.1259790000
_diffrn_orient_matrix_UB_32      -0.0027954000
_diffrn_orient_matrix_UB_33      -0.0774090000
_diffrn_oxdiff_digest_frames     
;
01c30885d407c795486d59e9060a2bc80a000301baf
;
_diffrn_oxdiff_digest_hkl        
;
01774a2b7b5419d7f27d00fb9b6948f3ff815d
;
_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_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4131
_reflns_number_total             4524
_reflns_odcompleteness_completeness 98.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (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         0.313
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.064
_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)+(0.0479P)²+0.5778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C20(H20), C10(H10), C18(H18), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B), C16(H16A,H16B), C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.39826(3) 0.18709(2) 0.83000(3) 0.02058(9) Uani 1 1 d . . . . .
Cl1 Cl 0.18320(4) 0.15395(2) 0.54645(4) 0.02325(10) Uani 1 1 d . . . . .
O1 O 0.33405(11) 0.32828(3) 0.37957(10) 0.01978(19) Uani 1 1 d . . . . .
O6 O 1.10528(10) 0.34527(3) 0.92920(10) 0.0198(2) Uani 1 1 d . . . . .
O3 O 0.40986(12) 0.49738(3) 0.68376(10) 0.0215(2) Uani 1 1 d . . . . .
O4 O 0.13419(11) 0.43646(4) 0.49876(11) 0.0223(2) Uani 1 1 d . . . . .
O5 O 0.26535(12) 0.44529(4) 0.33622(10) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.44616(12) 0.43547(4) 0.84624(10) 0.0237(2) Uani 1 1 d . . . . .
N1 N 0.54923(12) 0.42580(4) 0.54207(12) 0.0175(2) Uani 1 1 d . . . . .
H1 H 0.5578 0.4556 0.5175 0.021 Uiso 1 1 d R . . . .
C1 C 0.69536(14) 0.40728(5) 0.64275(14) 0.0173(2) Uani 1 1 d . . . . .
C20 C 0.39809(14) 0.23095(5) 0.56505(13) 0.0171(2) Uani 1 1 d . . . . .
H20 H 0.3726 0.2219 0.4609 0.021 Uiso 1 1 calc R . . . .
C6 C 0.86803(14) 0.33882(5) 0.73185(14) 0.0169(2) Uani 1 1 d . . . . .
H6 H 0.8914 0.3059 0.7277 0.020 Uiso 1 1 calc R . . . .
C10 C 0.40216(14) 0.36325(5) 0.62134(13) 0.0155(2) Uani 1 1 d . . . . .
H10 H 0.4911 0.3565 0.7119 0.019 Uiso 1 1 calc R . . . .
C12 C 0.42072(14) 0.45009(5) 0.72274(14) 0.0172(2) Uani 1 1 d . . . . .
C9 C 0.43917(15) 0.33825(5) 0.49345(13) 0.0157(2) Uani 1 1 d . . . . .
C22 C 0.63648(15) 0.27112(5) 0.52657(14) 0.0175(2) Uani 1 1 d . . . . .
H22A H 0.7494 0.2644 0.5551 0.021 Uiso 1 1 calc R . . . .
H22B H 0.5864 0.2567 0.4298 0.021 Uiso 1 1 calc R . . . .
C7 C 0.72863(14) 0.35730(5) 0.63375(13) 0.0163(2) Uani 1 1 d . . . . .
C14 C 0.26287(15) 0.43483(5) 0.45683(14) 0.0176(2) Uani 1 1 d . . . . .
C17 C 0.27038(15) 0.29328(5) 0.71200(14) 0.0181(3) Uani 1 1 d . . . . .
H17A H 0.3735 0.2909 0.7886 0.022 Uiso 1 1 calc R . . . .
H17B H 0.1898 0.2881 0.7580 0.022 Uiso 1 1 calc R . . . .
C11 C 0.40821(14) 0.41831(5) 0.58662(13) 0.0162(2) Uani 1 1 d . . . . .
C18 C 0.25679(14) 0.25356(5) 0.59910(14) 0.0171(2) Uani 1 1 d . . . . .
H18 H 0.1605 0.2560 0.5123 0.021 Uiso 1 1 calc R . . . .
C4 C 0.97497(14) 0.36877(5) 0.83745(14) 0.0179(3) Uani 1 1 d . . . . .
C16 C 0.25088(15) 0.34476(5) 0.64542(14) 0.0176(2) Uani 1 1 d . . . . .
H16A H 0.1649 0.3446 0.5515 0.021 Uiso 1 1 calc R . . . .
H16B H 0.2219 0.3671 0.7109 0.021 Uiso 1 1 calc R . . . .
C21 C 0.57085(15) 0.24518(5) 0.63771(14) 0.0177(2) Uani 1 1 d . . . . .
H21A H 0.6334 0.2162 0.6757 0.021 Uiso 1 1 calc R . . . .
H21B H 0.5804 0.2668 0.7204 0.021 Uiso 1 1 calc R . . . .
C2 C 0.80214(15) 0.43696(5) 0.74594(15) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.7790 0.4699 0.7505 0.025 Uiso 1 1 calc R . . . .
C3 C 0.94408(15) 0.41813(5) 0.84332(15) 0.0211(3) Uani 1 1 d . . . . .
H3 H 1.0163 0.4384 0.9107 0.025 Uiso 1 1 calc R . . . .
C8 C 0.61258(14) 0.32672(5) 0.51284(13) 0.0162(2) Uani 1 1 d . . . . .
H8 H 0.6284 0.3361 0.4201 0.019 Uiso 1 1 calc R . . . .
C19 C 0.30688(15) 0.20209(5) 0.64234(14) 0.0178(2) Uani 1 1 d . . . . .
C13 C 0.43917(19) 0.53239(5) 0.80355(16) 0.0274(3) Uani 1 1 d . . . . .
H13A H 0.4378 0.5649 0.7654 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.5411 0.5260 0.8762 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.3580 0.5294 0.8483 0.041 Uiso 1 1 calc GR . . . .
C5 C 1.22000(17) 0.37400(6) 1.03806(15) 0.0261(3) Uani 1 1 d . . . . .
H5A H 1.2611 0.3988 0.9899 0.039 Uiso 1 1 calc GR . . . .
H5B H 1.3054 0.3534 1.0952 0.039 Uiso 1 1 calc GR . . . .
H5C H 1.1705 0.3891 1.1021 0.039 Uiso 1 1 calc GR . . . .
C15 C -0.01342(17) 0.44858(6) 0.38358(18) 0.0292(3) Uani 1 1 d . . . . .
H15A H -0.0318 0.4259 0.3033 0.044 Uiso 1 1 calc GR . . . .
H15B H -0.0068 0.4811 0.3485 0.044 Uiso 1 1 calc GR . . . .
H15C H -0.0995 0.4468 0.4226 0.044 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
Cl2 C19 1.7602(13) . ?
Cl1 C19 1.7684(13) . ?
O1 C9 1.2113(16) . ?
O6 C4 1.3641(15) . ?
O6 C5 1.4308(16) . ?
O3 C12 1.3426(16) . ?
O3 C13 1.4518(16) . ?
O4 C14 1.3369(16) . ?
O4 C15 1.4489(17) . ?
O5 C14 1.1989(17) . ?
O2 C12 1.1984(16) . ?
N1 H1 0.8593 . ?
N1 C1 1.4330(16) . ?
N1 C11 1.4709(15) . ?
C1 C7 1.4092(18) . ?
C1 C2 1.3863(19) . ?
C20 H20 0.9800 . ?
C20 C18 1.5335(17) . ?
C20 C21 1.5166(17) . ?
C20 C19 1.4953(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3826(18) . ?
C6 C4 1.4026(18) . ?
C10 H10 0.9800 . ?
C10 C9 1.5333(16) . ?
C10 C11 1.5487(17) . ?
C10 C16 1.5288(16) . ?
C12 C11 1.5418(17) . ?
C9 C8 1.5284(17) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.5483(17) . ?
C22 C8 1.5371(18) . ?
C7 C8 1.5234(17) . ?
C14 C11 1.5376(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.5110(18) . ?
C17 C16 1.5334(18) . ?
C18 H18 0.9800 . ?
C18 C19 1.4952(18) . ?
C4 C3 1.384(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.3988(19) . ?
C3 H3 0.9300 . ?
C8 H8 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C4 O6 C5 117.48(11) . . ?
C12 O3 C13 116.05(10) . . ?
C14 O4 C15 115.61(11) . . ?
C1 N1 H1 112.1 . . ?
C1 N1 C11 115.43(10) . . ?
C11 N1 H1 112.0 . . ?
C7 C1 N1 117.73(11) . . ?
C2 C1 N1 121.98(12) . . ?
C2 C1 C7 120.28(12) . . ?
C18 C20 H20 113.0 . . ?
C21 C20 H20 113.0 . . ?
C21 C20 C18 125.45(11) . . ?
C19 C20 H20 113.0 . . ?
C19 C20 C18 59.15(8) . . ?
C19 C20 C21 123.03(11) . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C4 121.34(12) . . ?
C4 C6 H6 119.3 . . ?
C9 C10 H10 107.4 . . ?
C9 C10 C11 103.34(9) . . ?
C11 C10 H10 107.4 . . ?
C16 C10 H10 107.4 . . ?
C16 C10 C9 114.07(10) . . ?
C16 C10 C11 116.76(10) . . ?
O3 C12 C11 109.30(10) . . ?
O2 C12 O3 124.74(12) . . ?
O2 C12 C11 125.81(12) . . ?
O1 C9 C10 120.94(11) . . ?
O1 C9 C8 120.85(11) . . ?
C8 C9 C10 118.20(10) . . ?
H22A C22 H22B 107.4 . . ?
C21 C22 H22A 108.3 . . ?
C21 C22 H22B 108.3 . . ?
C8 C22 H22A 108.3 . . ?
C8 C22 H22B 108.3 . . ?
C8 C22 C21 116.10(10) . . ?
C1 C7 C8 118.47(11) . . ?
C6 C7 C1 118.29(12) . . ?
C6 C7 C8 123.20(12) . . ?
O4 C14 C11 110.11(10) . . ?
O5 C14 O4 125.07(12) . . ?
O5 C14 C11 124.81(11) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C18 C17 C16 113.10(10) . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
N1 C11 C10 107.00(10) . . ?
N1 C11 C12 109.78(10) . . ?
N1 C11 C14 107.25(10) . . ?
C12 C11 C10 111.43(10) . . ?
C14 C11 C10 112.35(10) . . ?
C14 C11 C12 108.92(10) . . ?
C20 C18 H18 113.4 . . ?
C17 C18 C20 124.54(11) . . ?
C17 C18 H18 113.4 . . ?
C19 C18 C20 59.15(8) . . ?
C19 C18 C17 122.30(11) . . ?
C19 C18 H18 113.4 . . ?
O6 C4 C6 114.82(12) . . ?
O6 C4 C3 124.95(12) . . ?
C3 C4 C6 120.23(12) . . ?
C10 C16 C17 112.55(10) . . ?
C10 C16 H16A 109.1 . . ?
C10 C16 H16B 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C20 C21 C22 111.11(10) . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.06(13) . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.75(12) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C9 C8 C22 108.72(10) . . ?
C9 C8 H8 106.3 . . ?
C22 C8 H8 106.3 . . ?
C7 C8 C9 112.58(10) . . ?
C7 C8 C22 116.06(10) . . ?
C7 C8 H8 106.3 . . ?
Cl2 C19 Cl1 110.81(7) . . ?
C20 C19 Cl2 119.11(9) . . ?
C20 C19 Cl1 118.97(9) . . ?
C18 C19 Cl2 119.86(9) . . ?
C18 C19 Cl1 118.75(9) . . ?
C18 C19 C20 61.70(8) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C5 H5A 109.5 . . ?
O6 C5 H5B 109.5 . . ?
O6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C8 C22 -70.86(14) . . . . ?
O1 C9 C8 C7 159.11(11) . . . . ?
O6 C4 C3 C2 -177.40(11) . . . . ?
O3 C12 C11 N1 67.67(13) . . . . ?
O3 C12 C11 C10 -173.99(10) . . . . ?
O3 C12 C11 C14 -49.49(13) . . . . ?
O4 C14 C11 N1 -169.95(10) . . . . ?
O4 C14 C11 C10 72.75(13) . . . . ?
O4 C14 C11 C12 -51.20(13) . . . . ?
O5 C14 C11 N1 9.19(17) . . . . ?
O5 C14 C11 C10 -108.11(14) . . . . ?
O5 C14 C11 C12 127.95(13) . . . . ?
O2 C12 C11 N1 -107.99(14) . . . . ?
O2 C12 C11 C10 10.35(17) . . . . ?
O2 C12 C11 C14 134.85(13) . . . . ?
N1 C1 C7 C6 -178.98(10) . . . . ?
N1 C1 C7 C8 3.32(16) . . . . ?
N1 C1 C2 C3 179.93(11) . . . . ?
C1 N1 C11 C10 -52.48(14) . . . . ?
C1 N1 C11 C12 68.58(14) . . . . ?
C1 N1 C11 C14 -173.23(10) . . . . ?
C1 C7 C8 C9 -42.20(15) . . . . ?
C1 C7 C8 C22 -168.38(10) . . . . ?
C1 C2 C3 C4 -1.50(19) . . . . ?
C20 C18 C19 Cl2 109.14(11) . . . . ?
C20 C18 C19 Cl1 -109.39(11) . . . . ?
C6 C7 C8 C9 140.21(12) . . . . ?
C6 C7 C8 C22 14.03(16) . . . . ?
C6 C4 C3 C2 2.31(18) . . . . ?
C10 C9 C8 C22 109.80(12) . . . . ?
C10 C9 C8 C7 -20.23(15) . . . . ?
C9 C10 C11 N1 -44.01(12) . . . . ?
C9 C10 C11 C12 -164.02(10) . . . . ?
C9 C10 C11 C14 73.44(12) . . . . ?
C9 C10 C16 C17 72.14(13) . . . . ?
C7 C1 C2 C3 -0.28(19) . . . . ?
C7 C6 C4 O6 178.36(10) . . . . ?
C7 C6 C4 C3 -1.39(18) . . . . ?
C17 C18 C19 Cl2 -4.67(16) . . . . ?
C17 C18 C19 Cl1 136.80(10) . . . . ?
C17 C18 C19 C20 -113.81(13) . . . . ?
C11 N1 C1 C7 82.84(14) . . . . ?
C11 N1 C1 C2 -97.37(14) . . . . ?
C11 C10 C9 O1 -88.53(13) . . . . ?
C11 C10 C9 C8 90.81(12) . . . . ?
C11 C10 C16 C17 -167.31(10) . . . . ?
C18 C20 C21 C22 -111.42(13) . . . . ?
C18 C20 C19 Cl2 -110.33(11) . . . . ?
C18 C20 C19 Cl1 109.04(11) . . . . ?
C18 C17 C16 C10 -79.48(13) . . . . ?
C4 C6 C7 C1 -0.41(17) . . . . ?
C4 C6 C7 C8 177.18(11) . . . . ?
C16 C10 C9 O1 39.26(16) . . . . ?
C16 C10 C9 C8 -141.40(11) . . . . ?
C16 C10 C11 N1 -170.10(10) . . . . ?
C16 C10 C11 C12 69.90(13) . . . . ?
C16 C10 C11 C14 -52.65(14) . . . . ?
C16 C17 C18 C20 93.62(14) . . . . ?
C16 C17 C18 C19 166.08(11) . . . . ?
C21 C20 C18 C17 -0.59(19) . . . . ?
C21 C20 C18 C19 -110.74(14) . . . . ?
C21 C20 C19 Cl2 4.35(17) . . . . ?
C21 C20 C19 Cl1 -136.28(11) . . . . ?
C21 C20 C19 C18 114.68(13) . . . . ?
C21 C22 C8 C9 -48.71(14) . . . . ?
C21 C22 C8 C7 79.39(13) . . . . ?
C2 C1 C7 C6 1.23(17) . . . . ?
C2 C1 C7 C8 -176.48(11) . . . . ?
C8 C22 C21 C20 87.66(13) . . . . ?
C19 C20 C18 C17 110.15(14) . . . . ?
C19 C20 C21 C22 175.31(11) . . . . ?
C13 O3 C12 O2 3.06(19) . . . . ?
C13 O3 C12 C11 -172.65(10) . . . . ?
C5 O6 C4 C6 179.14(10) . . . . ?
C5 O6 C4 C3 -1.13(18) . . . . ?
C15 O4 C14 O5 4.61(19) . . . . ?
C15 O4 C14 C11 -176.25(11) . . . . ?

_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 1.651
_oxdiff_exptl_absorpt_empirical_full_min 0.631
