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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9841-11478_htk145
_database_code_depnum_ccdc_archive 'CCDC 1994003'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl3 N3 O6'
_chemical_formula_sum            'C30 H24 Cl3 N3 O6'
_chemical_formula_weight         628.87
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9534(8)
_cell_length_b                   12.5947(13)
_cell_length_c                   13.2276(10)
_cell_angle_alpha                100.624(8)
_cell_angle_beta                 113.849(7)
_cell_angle_gamma                110.012(8)
_cell_volume                     1453.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5020
_cell_measurement_theta_min      4.4040
_shelx_estimated_absorpt_T_max   0.590
_shelx_estimated_absorpt_T_min   0.403
_exptl_absorpt_coefficient_mu    3.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.415
_diffrn_reflns_theta_min         3.942
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  36.00   1.00    1.00    --  -40.25  38.00  60.00   85
  2  ω     20.00 114.00   1.00    1.00    --   40.25  38.00 150.00   94
  3  ω    101.00 178.00   1.00    2.00    --  113.00 112.00  90.00   77
  4  ω    124.00 163.00   1.00    2.00    --  113.00 112.00  60.00   39
  5  ω    102.00 171.00   1.00    2.00    --  113.00 112.00 150.00   69
  6  ω    101.00 144.00   1.00    2.00    --  113.00  45.00  30.00   43
  7  ω     88.00 162.00   1.00    2.00    --  113.00  45.00 -90.00   74
  8  ω     89.00 160.00   1.00    2.00    --  113.00  77.00-150.00   71
  9  ω     82.00 169.00   1.00    2.00    --  113.00  77.00 -30.00   87
 10  ω     87.00 112.00   1.00    2.00    --  113.00 -77.00-180.00   25
 11  ω     78.00 115.00   1.00    2.00    --  113.00-112.00-180.00   37
 12  ω     53.00 114.00   1.00    2.00    --  113.00-112.00 -60.00   61
 13  ω     59.00 114.00   1.00    2.00    --  113.00-112.00  30.00   55
 14  ω    115.00 140.00   1.00    2.00    --  113.00 -77.00 120.00   25
 15  ω     57.00 113.00   1.00    2.00    --  113.00-112.00 120.00   56
 16  ω     46.00 137.00   1.00    2.00    --  113.00 -30.00  30.00   91
 17  ω     67.00  99.00   1.00    1.00    --   40.25-129.00 -99.00   32
 18  ω     35.00  86.00   1.00    2.00    --  113.00 -77.00-180.00   51
 19  ω     -5.00  70.00   1.00    1.00    --   40.25 -77.00-180.00   75
 20  ω     42.00  91.00   1.00    2.00    --  113.00-112.00  90.00   49
 21  ω     42.00  97.00   1.00    2.00    --  113.00 -77.00 120.00   55
 22  ω   -114.00 -15.00   1.00    1.00    --  -40.25 -57.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4696
_reflns_number_total             5941
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         1.252
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.059
_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)+(0.0829P)²+2.6003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1833
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C14(H14), C31(H31), C10(H10), C30(H30), C20(H20), C17(H17),
 C27(H27), C13(H13), C28(H28), C11(H11), C19(H19)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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 0.36525(9) 1.02087(7) 0.65977(8) 0.0307(2) Uani 1 1 d . . . . .
Cl3 Cl 1.18463(9) 0.85811(9) 1.23027(8) 0.0406(3) Uani 1 1 d . . . . .
Cl2 Cl -0.23696(14) -0.04405(10) 0.06795(9) 0.0573(4) Uani 1 1 d . . . . .
O6 O -0.0250(2) 0.4141(2) 0.7055(2) 0.0251(5) Uani 1 1 d . . . . .
O2 O 0.4242(2) 0.2292(2) 0.5570(2) 0.0242(5) Uani 1 1 d . . . . .
O1 O 0.4348(3) 0.3605(2) 0.4625(2) 0.0283(5) Uani 1 1 d . . . . .
O5 O 0.1653(3) 0.6049(2) 0.7941(2) 0.0316(6) Uani 1 1 d . . . . .
O4 O 0.6260(3) 0.3604(2) 0.8390(2) 0.0311(6) Uani 1 1 d . . . . .
O3 O 0.4170(3) 0.3220(3) 0.8501(2) 0.0356(6) Uani 1 1 d . . . . .
N2 N 0.3175(3) 0.4703(2) 0.5724(2) 0.0188(5) Uani 1 1 d . . . . .
H2 H 0.2990 0.4841 0.5062 0.023 Uiso 1 1 calc R . . . .
N3 N 0.4488(3) 0.5449(2) 0.7865(2) 0.0190(5) Uani 1 1 d . . . . .
N1 N 0.1290(3) 0.3329(2) 0.6342(2) 0.0197(5) Uani 1 1 d . . . . .
C5 C 0.4734(3) 0.4427(3) 0.7412(3) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.3521(3) 0.3761(3) 0.6054(3) 0.0188(6) Uani 1 1 d . . . . .
C15 C 0.0925(3) 0.1981(3) 0.4547(3) 0.0207(6) Uani 1 1 d . . . . .
C9 C 0.3329(3) 0.6594(3) 0.6778(3) 0.0208(6) Uani 1 1 d . . . . .
C4 C 0.2037(3) 0.2781(3) 0.5862(3) 0.0195(6) Uani 1 1 d . . . . .
H4 H 0.2290 0.2246 0.6294 0.023 Uiso 1 1 calc R . . . .
C21 C 0.4081(3) 0.3225(3) 0.5328(3) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.1821(3) 0.4478(3) 0.6753(3) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.1084(3) 0.4997(3) 0.7317(3) 0.0216(6) Uani 1 1 d . . . . .
C16 C 0.0215(3) 0.2439(3) 0.3742(3) 0.0220(6) Uani 1 1 d . . . . .
H16 H 0.0426 0.3268 0.4015 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2327(3) 0.6648(3) 0.5755(3) 0.0213(6) Uani 1 1 d . . . . .
H14 H 0.1572 0.5914 0.5087 0.026 Uiso 1 1 calc R . . . .
C2 C 0.3213(3) 0.5363(3) 0.6775(3) 0.0196(6) Uani 1 1 d . . . . .
C31 C 0.7469(3) 0.6386(3) 1.0001(3) 0.0220(6) Uani 1 1 d . . . . .
H31 H 0.6604 0.5918 1.0029 0.026 Uiso 1 1 calc R . . . .
C25 C 0.5866(3) 0.5716(3) 0.7772(3) 0.0195(6) Uani 1 1 d . . . . .
H25 H 0.5847 0.5970 0.7095 0.023 Uiso 1 1 calc R . . . .
C26 C 0.7330(3) 0.6400(3) 0.8910(3) 0.0216(6) Uani 1 1 d . . . . .
C12 C 0.3522(3) 0.8806(3) 0.6668(3) 0.0242(7) Uani 1 1 d . . . . .
C10 C 0.4437(4) 0.7669(3) 0.7752(3) 0.0267(7) Uani 1 1 d . . . . .
H10 H 0.5128 0.7639 0.8456 0.032 Uiso 1 1 calc R . . . .
C30 C 0.8853(4) 0.7044(3) 1.1044(3) 0.0258(7) Uani 1 1 d . . . . .
H30 H 0.8945 0.7023 1.1784 0.031 Uiso 1 1 calc R . . . .
C20 C 0.0618(3) 0.0767(3) 0.4138(3) 0.0255(7) Uani 1 1 d . . . . .
H20 H 0.1107 0.0449 0.4679 0.031 Uiso 1 1 calc R . . . .
C17 C -0.0797(3) 0.1702(3) 0.2546(3) 0.0257(7) Uani 1 1 d . . . . .
H17 H -0.1276 0.2018 0.1998 0.031 Uiso 1 1 calc R . . . .
C27 C 0.8600(3) 0.7122(3) 0.8886(3) 0.0259(7) Uani 1 1 d . . . . .
H27 H 0.8511 0.7159 0.8150 0.031 Uiso 1 1 calc R . . . .
C23 C 0.5012(4) 0.3680(3) 0.8158(3) 0.0270(7) Uani 1 1 d . . . . .
C13 C 0.2408(3) 0.7755(3) 0.5691(3) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.1714 0.7788 0.4992 0.025 Uiso 1 1 calc R . . . .
C28 C 0.9991(4) 0.7785(3) 0.9925(3) 0.0297(7) Uani 1 1 d . . . . .
H28 H 1.0857 0.8268 0.9903 0.036 Uiso 1 1 calc R . . . .
C11 C 0.4537(4) 0.8781(3) 0.7701(3) 0.0283(7) Uani 1 1 d . . . . .
H11 H 0.5292 0.9516 0.8366 0.034 Uiso 1 1 calc R . . . .
C29 C 1.0104(4) 0.7736(3) 1.0991(3) 0.0295(7) Uani 1 1 d . . . . .
C19 C -0.0399(4) 0.0016(3) 0.2944(3) 0.0331(8) Uani 1 1 d . . . . .
H19 H -0.0613 -0.0814 0.2666 0.040 Uiso 1 1 calc R . . . .
C18 C -0.1090(4) 0.0494(3) 0.2172(3) 0.0320(8) Uani 1 1 d . . . . .
C8 C -0.1008(4) 0.4569(4) 0.7586(4) 0.0348(8) Uani 1 1 d . . . . .
H8A H -0.1203 0.5193 0.7305 0.052 Uiso 1 1 calc GR . . . .
H8B H -0.0368 0.4918 0.8456 0.052 Uiso 1 1 calc GR . . . .
H8C H -0.1965 0.3883 0.7354 0.052 Uiso 1 1 calc GR . . . .
C22 C 0.4728(4) 0.1666(3) 0.4897(4) 0.0341(8) Uani 1 1 d . . . . .
H22A H 0.3984 0.1333 0.4044 0.051 Uiso 1 1 calc GR . . . .
H22B H 0.4823 0.1001 0.5150 0.051 Uiso 1 1 calc GR . . . .
H22C H 0.5705 0.2243 0.5042 0.051 Uiso 1 1 calc GR . . . .
C24 C 0.6627(6) 0.2982(5) 0.9213(4) 0.0516(12) Uani 1 1 d . . . . .
H24A H 0.5918 0.2109 0.8806 0.077 Uiso 1 1 calc GR . . . .
H24B H 0.6554 0.3322 0.9903 0.077 Uiso 1 1 calc GR . . . .
H24C H 0.7655 0.3097 0.9483 0.077 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 C12 1.746(3) . ?
Cl3 C29 1.743(4) . ?
Cl2 C18 1.739(3) . ?
O6 C7 1.338(4) . ?
O6 C8 1.453(3) . ?
O2 C21 1.323(4) . ?
O2 C22 1.452(4) . ?
O1 C21 1.211(4) . ?
O5 C7 1.201(4) . ?
O4 C23 1.316(4) . ?
O4 C24 1.462(5) . ?
O3 C23 1.209(5) . ?
N2 H2 0.8800 . ?
N2 C3 1.452(4) . ?
N2 C2 1.459(4) . ?
N3 C5 1.474(4) . ?
N3 C2 1.500(4) . ?
N3 C25 1.492(4) . ?
N1 C4 1.481(3) . ?
N1 C1 1.268(4) . ?
C5 C3 1.564(4) . ?
C5 C25 1.503(4) . ?
C5 C23 1.499(5) . ?
C3 C4 1.552(4) . ?
C3 C21 1.509(4) . ?
C15 C4 1.524(4) . ?
C15 C16 1.391(5) . ?
C15 C20 1.393(5) . ?
C9 C14 1.387(4) . ?
C9 C2 1.510(4) . ?
C9 C10 1.391(5) . ?
C4 H4 1.0000 . ?
C1 C7 1.518(4) . ?
C1 C2 1.535(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(5) . ?
C31 H31 0.9500 . ?
C31 C26 1.393(5) . ?
C31 C30 1.384(4) . ?
C25 H25 1.0000 . ?
C25 C26 1.484(4) . ?
C26 C27 1.394(5) . ?
C12 C13 1.379(5) . ?
C12 C11 1.385(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
C30 H30 0.9500 . ?
C30 C29 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C19 1.392(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(5) . ?
C13 H13 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.380(5) . ?
C11 H11 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.376(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C7 O6 C8 115.1(3) . . ?
C21 O2 C22 116.1(3) . . ?
C23 O4 C24 112.9(3) . . ?
C3 N2 H2 129.0 . . ?
C3 N2 C2 101.9(2) . . ?
C2 N2 H2 129.0 . . ?
C5 N3 C2 103.4(2) . . ?
C5 N3 C25 60.88(19) . . ?
C25 N3 C2 112.4(2) . . ?
C1 N1 C4 119.6(3) . . ?
N3 C5 C3 106.3(2) . . ?
N3 C5 C25 60.15(19) . . ?
N3 C5 C23 117.5(3) . . ?
C25 C5 C3 115.3(3) . . ?
C23 C5 C3 119.0(3) . . ?
C23 C5 C25 122.6(3) . . ?
N2 C3 C5 103.7(2) . . ?
N2 C3 C4 105.7(2) . . ?
N2 C3 C21 112.4(3) . . ?
C4 C3 C5 110.7(2) . . ?
C21 C3 C5 112.5(2) . . ?
C21 C3 C4 111.4(2) . . ?
C16 C15 C4 121.4(3) . . ?
C16 C15 C20 119.1(3) . . ?
C20 C15 C4 119.5(3) . . ?
C14 C9 C2 118.5(3) . . ?
C14 C9 C10 119.4(3) . . ?
C10 C9 C2 122.1(3) . . ?
N1 C4 C3 112.1(2) . . ?
N1 C4 C15 108.6(2) . . ?
N1 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
C15 C4 C3 111.8(3) . . ?
C15 C4 H4 108.1 . . ?
O2 C21 C3 110.6(3) . . ?
O1 C21 O2 125.1(3) . . ?
O1 C21 C3 124.3(3) . . ?
N1 C1 C7 117.5(3) . . ?
N1 C1 C2 123.6(2) . . ?
C7 C1 C2 118.8(3) . . ?
O6 C7 C1 112.1(3) . . ?
O5 C7 O6 124.5(3) . . ?
O5 C7 C1 123.4(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
N2 C2 N3 108.5(2) . . ?
N2 C2 C9 110.5(3) . . ?
N2 C2 C1 104.7(2) . . ?
N3 C2 C9 112.9(2) . . ?
N3 C2 C1 102.6(2) . . ?
C9 C2 C1 117.0(2) . . ?
C26 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C26 120.8(3) . . ?
N3 C25 C5 58.97(18) . . ?
N3 C25 H25 115.0 . . ?
C5 C25 H25 115.0 . . ?
C26 C25 N3 116.4(3) . . ?
C26 C25 C5 124.4(3) . . ?
C26 C25 H25 115.0 . . ?
C31 C26 C25 122.6(3) . . ?
C31 C26 C27 118.9(3) . . ?
C27 C26 C25 118.4(3) . . ?
C13 C12 Cl1 118.9(3) . . ?
C13 C12 C11 121.9(3) . . ?
C11 C12 Cl1 119.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C31 C30 H30 120.5 . . ?
C31 C30 C29 119.0(3) . . ?
C29 C30 H30 120.5 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 H17 120.8 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
O4 C23 C5 112.3(3) . . ?
O3 C23 O4 125.3(3) . . ?
O3 C23 C5 122.4(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13 120.9 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.2(3) . . ?
C29 C28 H28 120.4 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.1(3) . . ?
C10 C11 H11 120.5 . . ?
C30 C29 Cl3 119.2(3) . . ?
C28 C29 Cl3 119.4(3) . . ?
C28 C29 C30 121.4(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.6 . . ?
C17 C18 Cl2 118.8(3) . . ?
C19 C18 Cl2 119.2(3) . . ?
C19 C18 C17 122.0(3) . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
;
####################################################################### 
# 
# 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_15893_htk03
_database_code_depnum_ccdc_archive 'CCDC 1994004'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O6'
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 N2 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0485(3)
_cell_length_b                   13.9573(3)
_cell_length_c                   10.3547(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.580(2)
_cell_angle_gamma                90
_cell_volume                     2002.03(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3270
_cell_measurement_theta_min      3.0520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96739
_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_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.701
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -17.00   1.00   84.45    --  -19.04 -57.00 150.00   71
  2  ω    -93.00  27.00   1.00   84.45    --  -19.04 -19.00-180.00  120
  3  ω     16.00  57.00   1.00   84.45    --   20.06 -99.00 -30.00   41
  4  ω    -56.00  42.00   1.00   84.45    --  -19.04  19.00 -30.00   98
  5  ω    -81.00 -49.00   1.00   84.45    --  -19.04 -38.00 -30.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319910000
_diffrn_orient_matrix_UB_12      -0.0030990000
_diffrn_orient_matrix_UB_13      -0.0460866000
_diffrn_orient_matrix_UB_21      0.0385909000
_diffrn_orient_matrix_UB_22      0.0155781000
_diffrn_orient_matrix_UB_23      0.0485410000
_diffrn_orient_matrix_UB_31      0.0104303000
_diffrn_orient_matrix_UB_32      -0.0482725000
_diffrn_orient_matrix_UB_33      0.0186321000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3626
_reflns_number_total             4451
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    ?
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.7207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C17(H17), C14(H14), C9(H9), C16(H16), C8(H8), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C11(H11A,H11B,
 H11C)
;
_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
O2 O 0.65997(7) 0.33180(7) 0.39204(10) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.47869(7) 0.34199(7) 0.56080(10) 0.0186(2) Uani 1 1 d . . . . .
O6 O 0.87286(7) 0.55520(7) 0.95719(10) 0.0216(2) Uani 1 1 d . . . . .
O4 O 0.88010(7) 0.56924(7) 0.50822(10) 0.0210(2) Uani 1 1 d . . . . .
O5 O 0.79122(8) 0.69248(8) 0.91236(12) 0.0298(3) Uani 1 1 d . . . . .
N2 N 0.62627(8) 0.46639(8) 0.59036(11) 0.0141(2) Uani 1 1 d . . . . .
N1 N 0.66365(8) 0.51897(8) 0.80780(11) 0.0160(2) Uani 1 1 d . . . . .
O3 O 0.91968(8) 0.63908(9) 0.70561(12) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.60371(9) 0.48068(9) 0.70905(13) 0.0139(3) Uani 1 1 d . . . . .
C4 C 0.74931(9) 0.55351(10) 0.77665(14) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.78033(9) 0.53953(10) 0.66127(14) 0.0154(3) Uani 1 1 d . . . . .
C21 C 0.80625(9) 0.61085(10) 0.88670(14) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.44311(9) 0.38948(10) 0.65867(13) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.50402(9) 0.45772(10) 0.73139(13) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.76997(9) 0.36803(10) 0.58007(13) 0.0146(3) Uani 1 1 d . . . . .
C19 C 0.86673(10) 0.58790(10) 0.63112(14) 0.0190(3) Uani 1 1 d . . . . .
C2 C 0.72701(9) 0.46860(10) 0.56651(13) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.7275 0.4919 0.4753 0.016 Uiso 1 1 calc R . . . .
C7 C 0.35201(10) 0.37082(10) 0.68907(14) 0.0193(3) Uani 1 1 d . . . . .
H7 H 0.3115 0.3242 0.6408 0.023 Uiso 1 1 calc R . . . .
C10 C 0.46965(10) 0.50551(10) 0.83260(14) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.5099 0.5514 0.8828 0.022 Uiso 1 1 calc R . . . .
C17 C 0.84240(10) 0.34133(10) 0.68181(14) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.8679 0.3873 0.7460 0.022 Uiso 1 1 calc R . . . .
C13 C 0.73274(9) 0.29918(10) 0.48664(14) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.76765(10) 0.20593(10) 0.49508(15) 0.0212(3) Uani 1 1 d . . . . .
H14 H 0.7422 0.1595 0.4315 0.025 Uiso 1 1 calc R . . . .
C9 C 0.37847(10) 0.48816(11) 0.86229(14) 0.0226(3) Uani 1 1 d . . . . .
H9 H 0.3562 0.5221 0.9310 0.027 Uiso 1 1 calc R . . . .
C16 C 0.87824(10) 0.24801(11) 0.69120(15) 0.0229(3) Uani 1 1 d . . . . .
H16 H 0.9280 0.2305 0.7609 0.027 Uiso 1 1 calc R . . . .
C8 C 0.32064(10) 0.42051(11) 0.78996(15) 0.0222(3) Uani 1 1 d . . . . .
H8 H 0.2582 0.4078 0.8098 0.027 Uiso 1 1 calc R . . . .
C18 C 0.62390(11) 0.26768(11) 0.28798(15) 0.0242(3) Uani 1 1 d . . . . .
H18A H 0.5711 0.2985 0.2288 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.6000 0.2093 0.3243 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.6758 0.2512 0.2394 0.036 Uiso 1 1 calc GR . . . .
C15 C 0.84063(11) 0.18140(11) 0.59816(16) 0.0239(3) Uani 1 1 d . . . . .
H15 H 0.8649 0.1177 0.6044 0.029 Uiso 1 1 calc R . . . .
C20 C 0.95949(11) 0.61832(11) 0.46414(16) 0.0265(3) Uani 1 1 d . . . . .
H20A H 0.9705 0.5906 0.3810 0.040 Uiso 1 1 calc GR . . . .
H20B H 1.0179 0.6112 0.5299 0.040 Uiso 1 1 calc GR . . . .
H20C H 0.9438 0.6865 0.4517 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.93615(11) 0.60231(12) 1.06311(15) 0.0260(3) Uani 1 1 d . . . . .
H22A H 0.9812 0.6440 1.0268 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.9725 0.5540 1.1197 0.039 Uiso 1 1 calc GR . . . .
H22C H 0.8975 0.6408 1.1144 0.039 Uiso 1 1 calc GR . . . .
C11 C 0.41842(11) 0.27127(11) 0.48775(16) 0.0259(3) Uani 1 1 d . . . . .
H11A H 0.4529 0.2419 0.4231 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.3592 0.3017 0.4427 0.039 Uiso 1 1 calc GR . . . .
H11C H 0.4018 0.2219 0.5475 0.039 Uiso 1 1 calc GR . . . .
H2 H 0.5836(12) 0.4347(12) 0.5306(17) 0.028(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.3707(17) . ?
O2 C18 1.4273(17) . ?
O1 C6 1.3729(16) . ?
O1 C11 1.4318(17) . ?
O6 C21 1.3358(17) . ?
O6 C22 1.4495(17) . ?
O4 C19 1.3424(17) . ?
O4 C20 1.4459(16) . ?
O5 C21 1.1967(17) . ?
N2 C1 1.3342(18) . ?
N2 C2 1.4769(16) . ?
N1 C1 1.3243(17) . ?
N1 C4 1.3833(17) . ?
O3 C19 1.2114(18) . ?
C1 C5 1.4918(18) . ?
C4 C3 1.3524(19) . ?
C4 C21 1.5085(19) . ?
C3 C19 1.4672(19) . ?
C3 C2 1.5031(18) . ?
C6 C5 1.4114(19) . ?
C6 C7 1.3925(19) . ?
C5 C10 1.395(2) . ?
C12 C2 1.5252(19) . ?
C12 C17 1.3883(19) . ?
C12 C13 1.4015(19) . ?
C7 C8 1.386(2) . ?
C10 C9 1.3875(19) . ?
C17 C16 1.394(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.394(2) . ?
C9 C8 1.382(2) . ?
C16 C15 1.379(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C18 117.39(11) . . ?
C6 O1 C11 117.82(11) . . ?
C21 O6 C22 115.81(11) . . ?
C19 O4 C20 116.37(11) . . ?
C1 N2 C2 122.15(11) . . ?
C1 N1 C4 115.26(12) . . ?
N2 C1 C5 118.94(12) . . ?
N1 C1 N2 123.61(12) . . ?
N1 C1 C5 117.37(12) . . ?
N1 C4 C21 112.42(12) . . ?
C3 C4 N1 125.20(12) . . ?
C3 C4 C21 122.38(12) . . ?
C4 C3 C19 121.42(12) . . ?
C4 C3 C2 118.22(12) . . ?
C19 C3 C2 120.28(12) . . ?
O6 C21 C4 109.85(11) . . ?
O5 C21 O6 124.45(13) . . ?
O5 C21 C4 125.58(13) . . ?
O1 C6 C5 117.18(11) . . ?
O1 C6 C7 122.54(12) . . ?
C7 C6 C5 120.27(13) . . ?
C6 C5 C1 124.31(12) . . ?
C10 C5 C1 117.72(12) . . ?
C10 C5 C6 117.95(12) . . ?
C17 C12 C2 123.07(12) . . ?
C17 C12 C13 118.81(13) . . ?
C13 C12 C2 118.10(12) . . ?
O4 C19 C3 111.32(12) . . ?
O3 C19 O4 123.37(13) . . ?
O3 C19 C3 125.30(14) . . ?
N2 C2 C3 106.97(11) . . ?
N2 C2 C12 109.93(11) . . ?
C3 C2 C12 113.55(11) . . ?
C8 C7 C6 119.76(13) . . ?
C9 C10 C5 122.06(14) . . ?
C12 C17 C16 120.95(14) . . ?
O2 C13 C12 114.44(12) . . ?
O2 C13 C14 124.75(13) . . ?
C14 C13 C12 120.79(13) . . ?
C13 C14 C15 119.04(14) . . ?
C8 C9 C10 118.71(14) . . ?
C15 C16 C17 119.29(14) . . ?
C9 C8 C7 121.24(13) . . ?
C16 C15 C14 121.12(14) . . ?

_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 1.097
_oxdiff_exptl_absorpt_empirical_full_min 0.912
####################################################################### 
# 
# 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_15289_htk-02
_database_code_depnum_ccdc_archive 'CCDC 1994005'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;
_audit_creation_date             2020-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Cl4 N2 O4'
_chemical_formula_sum            'C20 H14 Cl4 N2 O4'
_chemical_formula_weight         488.13
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H14 Cl4 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.82480(10)
_cell_length_b                   16.44070(10)
_cell_length_c                   12.04070(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.7710(10)
_cell_angle_gamma                90
_cell_volume                     2016.53(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19869
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2600
_cell_measurement_theta_min      3.8950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25202
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.448
_diffrn_reflns_theta_min         3.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   6.00   0.50    0.40    --   38.95 -54.00-138.00   52
  2  ω     29.00  64.00   0.50    0.40    --   38.95  54.00   6.00   70
  3  ω     67.00 102.00   0.50    0.40    --   38.95  54.00   6.00   70
  4  ω     80.00 141.00   0.50    0.90    --  100.00  54.00   6.00  122
  5  ω     70.00 118.00   0.50    0.90    --  100.00 -54.00-138.00   96
  6  ω     42.00  68.00   0.50    0.90    --  100.00 -54.00-138.00   52
  7  ω     -7.00  21.00   0.50    0.40    --  -38.95  32.00 120.00   56
  8  ω    -46.00 -20.00   0.50    0.40    --  -38.95  32.00 120.00   52
  9  ω    -72.00 -46.00   0.50    0.40    --  -38.95 -21.00-120.00   52
 10  ω    -46.00 -21.00   0.50    0.40    --  -38.95 -54.00-138.00   50
 11  ω    -80.00 -54.00   0.50    0.40    --  -38.95 -54.00-138.00   52
 12  ω    -56.00  25.00   0.50    0.40    --  -38.95  43.00-180.00  162
 13  ω   -107.00 -79.00   0.50    0.40    --  -38.95 -21.00-120.00   56
 14  ω    -34.00  -8.00   0.50    0.40    --  -38.95  54.00   6.00   52
 15  ω     23.00  49.00   0.50    0.40    --   38.95  21.00  90.00   52
 16  ω     76.00 106.00   0.50    0.40    --   38.95  21.00 -30.00   60
 17  ω     32.00 100.00   0.50    0.40    --   38.95  65.00  30.00  136
 18  ω     24.00  72.00   0.50    0.40    --   38.95  21.00 -30.00   96
 19  ω     22.00  49.00   0.50    0.40    --   38.95 -54.00-138.00   54
 20  ω     76.00 102.00   0.50    0.40    --   38.95  21.00  90.00   52
 21  ω    -17.00  53.00   0.50    0.40    --   38.95 -43.00  90.00  140
 22  ω     35.00  61.00   0.50    0.40    --   38.95  32.00   0.00   52
 23  ω     31.00  80.00   0.50    0.90    --  100.00-111.00 -90.00   98
 24  ω    130.00 156.00   0.50    0.90    --  100.00   7.00 -30.00   52
 25  ω     78.00 124.00   0.50    0.90    --  100.00 -69.00   0.00   92
 26  ω     84.00 155.00   0.50    0.90    --  100.00 133.00-120.00  142
 27  ω     94.00 119.00   0.50    0.90    --  100.00 -22.00  90.00   50
 28  ω     61.00  93.00   0.50    0.90    --  100.00   7.00 -30.00   64
 29  ω     63.00  89.00   0.50    0.90    --  100.00 -22.00  90.00   52
 30  ω     83.00 114.00   0.50    0.90    --  100.00 -30.00-180.00   62
 31  ω     46.00 116.00   0.50    0.90    --  100.00 -45.00  90.00  140
 32  ω     32.00  63.00   0.50    0.90    --  100.00 -30.00-180.00   62
 33  ω     83.00 110.00   0.50    0.90    --  100.00 -45.00   0.00   54
 34  ω    108.00 156.00   0.50    0.90    --  100.00  93.00  60.00   96
 35  ω     78.00 125.00   0.50    0.90    --  100.00  61.00 150.00   94
 36  ω     31.00  75.00   0.50    0.90    --  100.00 -30.00  30.00   88
 37  ω     84.00 125.00   0.50    0.90    --  100.00 111.00  60.00   82
 38  ω     61.00 104.00   0.50    0.90    --  100.00 -61.00   0.00   86
 39  ω    107.00 133.00   0.50    0.90    --  100.00  30.00  90.00   52
 40  ω    101.00 157.00   0.50    0.90    --  100.00  93.00-150.00  112
 41  ω     86.00 134.00   0.50    0.90    --  100.00 111.00 -90.00   96
 42  ω     86.00 152.00   0.50    0.90    --  100.00  53.00 -30.00  132
 43  ω     93.00 147.00   0.50    0.90    --  100.00  93.00 -30.00  108
 44  ω     40.00  66.00   0.50    0.90    --  100.00 -54.00-138.00   52
 45  ω    -77.00 -25.00   0.50    0.40    --  -38.95 -32.00  90.00  104
 46  ω     18.00  56.00   0.50    0.40    --   38.95  65.00 120.00   76
 47  ω     82.00 108.00   0.50    0.40    --   38.95  32.00-150.00   52
 48  ω     61.00 101.00   0.50    0.40    --   38.95  65.00 120.00   80
 49  ω     21.00  90.00   0.50    0.40    --   38.95  65.00 150.00  138
 50  ω     15.00  59.00   0.50    0.40    --   38.95 -11.00-150.00   88
 51  ω    -27.00   6.00   0.50    0.40    --   38.95 -11.00-150.00   66
 52  ω     -3.00  48.00   0.50    0.40    --   38.95 -32.00 120.00  102
 53  ω     31.00  57.00   0.50    0.40    --   38.95  65.00  90.00   52
 54  ω     63.00  97.00   0.50    0.40    --   38.95  65.00  90.00   68
 55  ω     86.00 114.00   0.50    0.90    --  100.00  53.00 -60.00   56
 56  ω     76.00 101.00   0.50    0.90    --  100.00  69.00 120.00   50
 57  ω     78.00 110.00   0.50    0.90    --  100.00  61.00 120.00   64
 58  ω    106.00 153.00   0.50    0.90    --  100.00  93.00   0.00   94
 59  ω    114.00 157.00   0.50    0.90    --  100.00  67.00  99.99   86
 60  ω    121.00 154.00   0.50    0.90    --  100.00  69.00  30.00   66
 61  ω    132.00 157.00   0.50    0.90    --  100.00  69.00  60.00   50
 62  ω     93.00 119.00   0.50    0.90    --  100.00  69.00  30.00   52
 63  ω     84.00 110.00   0.50    0.90    --  100.00  45.00 150.00   52
 64  ω    110.00 136.00   0.50    0.90    --  100.00 133.00 120.00   52
 65  ω    118.00 157.00   0.50    0.90    --  100.00 133.00 150.00   78
 66  ω     76.00 102.00   0.50    0.90    --  100.00  67.00  99.99   52
 67  ω    113.00 149.00   0.50    0.90    --  100.00  77.00 120.00   72
 68  ω     80.00 121.00   0.50    0.90    --  100.00  53.00 150.00   82
 69  ω    127.00 153.00   0.50    0.90    --  100.00  53.00 150.00   52
 70  ω     75.00 108.00   0.50    0.90    --  100.00-111.00-120.00   66
 71  ω    132.00 157.00   0.50    0.90    --  100.00  69.00  90.00   50
 72  ω    120.00 146.00   0.50    0.90    --  100.00  61.00 120.00   52
 73  ω     76.00 112.00   0.50    0.90    --  100.00  69.00  60.00   72
 74  ω     36.00  61.00   0.50    0.90    --  100.00-133.00  30.00   50
 75  ω     80.00 120.00   0.50    0.90    --  100.00  53.00-180.00   80
 76  ω     86.00 115.00   0.50    0.90    --  100.00  61.00-150.00   58
 77  ω     80.00 106.00   0.50    0.90    --  100.00  53.00  90.00   52
 78  ω     76.00 105.00   0.50    0.90    --  100.00  69.00  90.00   58
 79  ω     83.00 109.00   0.50    0.90    --  100.00  45.00  90.00   52
 80  ω    132.00 157.00   0.50    0.90    --  100.00  61.00-150.00   50
 81  ω     78.00 107.00   0.50    0.90    --  100.00  61.00  90.00   58
 82  ω     43.00  94.00   0.50    0.90    --  100.00 -93.00  60.00  102
 83  ω     79.00 104.00   0.50    0.90    --  100.00  61.00  60.00   50
 84  ω     82.00 130.00   0.50    0.90    --  100.00 -86.00-180.00   96
 85  ω     76.00 101.00   0.50    0.90    --  100.00  69.00 150.00   50
 86  ω     26.00  51.00   0.50    0.90    --  100.00 -93.00 -30.00   50
 87  ω    108.00 140.00   0.50    0.90    --  100.00 111.00  30.00   64
 88  ω     83.00 109.00   0.50    0.90    --  100.00  77.00  60.00   52
 89  ω     83.00 108.00   0.50    0.90    --  100.00  77.00  90.00   50
 90  ω     83.00 109.00   0.50    0.90    --  100.00  77.00 120.00   52
 91  ω    130.00 156.00   0.50    0.90    --  100.00  53.00 -60.00   52
 92  ω    106.00 131.00   0.50    0.90    --  100.00  22.00 -60.00   50
 93  ω     82.00 108.00   0.50    0.90    --  100.00-111.00-180.00   52
 94  ω     37.00  65.00   0.50    0.90    --  100.00-111.00   0.00   56
 95  ω     86.00 120.00   0.50    0.90    --  100.00  37.00  60.00   68
 96  ω     80.00 110.00   0.50    0.90    --  100.00  53.00 120.00   60
;
_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      0.1369845000
_diffrn_orient_matrix_UB_12      -0.0247362000
_diffrn_orient_matrix_UB_13      0.0841085000
_diffrn_orient_matrix_UB_21      0.0640861000
_diffrn_orient_matrix_UB_22      0.0555530000
_diffrn_orient_matrix_UB_23      -0.0680923000
_diffrn_orient_matrix_UB_31      -0.0024101000
_diffrn_orient_matrix_UB_32      0.0712990000
_diffrn_orient_matrix_UB_33      0.0822795000
_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'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                7401
_reflns_number_total             7584
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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    ?
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 3387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7584
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.031
_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)+(0.0340P)²+0.0377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0585
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C2A(H2AB)
2.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C16(H16), C15(H15), C15A(H15A), C10A(H10A), C13(H13), C7(H7),
 C10(H10), C9(H9), C13A(H13A), C9A(H9A), C16A(H16A)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F), C20A(H20D,
 H20E,H20F)
;
_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
Cl3 Cl 0.77991(6) 0.46437(4) 0.32231(5) 0.01716(13) Uani 1 1 d . . . . .
Cl2A Cl 0.00367(6) 0.31701(4) 0.31563(6) 0.02028(14) Uani 1 1 d . . . . .
Cl1 Cl 1.19783(6) 0.67109(4) 1.02248(6) 0.02126(14) Uani 1 1 d . . . . .
Cl2 Cl 0.97906(6) 0.57293(4) 0.57482(6) 0.02133(14) Uani 1 1 d . . . . .
Cl3A Cl 0.44331(6) 0.56415(4) 0.96937(6) 0.02088(14) Uani 1 1 d . . . . .
Cl1A Cl 0.24837(6) 0.42868(4) 0.75234(5) 0.02075(14) Uani 1 1 d . . . . .
Cl4 Cl 0.70510(7) 0.73016(4) 0.05012(6) 0.02208(14) Uani 1 1 d . . . . .
Cl4A Cl 0.46509(7) 0.29822(5) 1.23328(6) 0.02363(15) Uani 1 1 d . . . . .
O3A O 0.87425(19) 0.39077(12) 0.64542(16) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.31914(19) 0.71459(12) 0.53452(17) 0.0170(4) Uani 1 1 d . . . . .
O3 O 0.34142(19) 0.61153(12) 0.66256(17) 0.0178(4) Uani 1 1 d . . . . .
O4A O 0.88550(19) 0.28613(12) 0.76952(17) 0.0195(4) Uani 1 1 d . . . . .
O2 O 0.23209(18) 0.56183(13) 0.39381(17) 0.0187(4) Uani 1 1 d . . . . .
O1A O 0.8938(2) 0.50421(13) 1.02732(17) 0.0215(4) Uani 1 1 d . . . . .
O1 O 0.32953(19) 0.50158(13) 0.27740(17) 0.0212(4) Uani 1 1 d . . . . .
O2A O 0.98366(19) 0.42991(14) 0.91708(17) 0.0218(4) Uani 1 1 d . . . . .
N1A N 0.6117(2) 0.36403(14) 0.6889(2) 0.0159(5) Uani 1 1 d . . . . .
N2 N 0.6931(2) 0.53805(14) 0.5428(2) 0.0143(4) Uani 1 1 d . . . . .
N2A N 0.5259(2) 0.47524(14) 0.7592(2) 0.0152(4) Uani 1 1 d . . . . .
N1 N 0.6009(2) 0.64305(14) 0.61938(19) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.8305(3) 0.61725(16) 0.7118(2) 0.0151(5) Uani 1 1 d . . . . .
C17A C 0.8824(3) 0.46376(17) 0.9402(2) 0.0164(5) Uani 1 1 d . . . . .
C19A C 0.8406(3) 0.35694(16) 0.7202(2) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.7028(3) 0.59941(16) 0.6187(2) 0.0139(5) Uani 1 1 d . . . . .
C19 C 0.3711(3) 0.64540(16) 0.5861(2) 0.0140(5) Uani 1 1 d . . . . .
C4 C 0.4804(3) 0.61564(16) 0.5447(2) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.5848(2) 0.53703(16) 0.4289(2) 0.0145(5) Uani 1 1 d . . . . .
H2A H 0.5710 0.4796 0.4000 0.017 Uiso 1 1 calc R . . . .
C5A C 0.3821(3) 0.38916(16) 0.6014(2) 0.0151(5) Uani 1 1 d . . . . .
C7A C 0.1435(3) 0.37489(17) 0.5323(2) 0.0172(5) Uani 1 1 d . . . . .
H7A H 0.0620 0.3816 0.5447 0.021 Uiso 1 1 calc R . . . .
C16 C 0.5650(3) 0.66518(17) 0.3034(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.5072 0.6872 0.3399 0.019 Uiso 1 1 calc R . . . .
C15 C 0.5933(3) 0.71066(17) 0.2181(2) 0.0176(5) Uani 1 1 d . . . . .
H15 H 0.5558 0.7630 0.1964 0.021 Uiso 1 1 calc R . . . .
C15A C 0.6058(3) 0.31423(18) 1.0878(2) 0.0180(5) Uani 1 1 d . . . . .
H15A H 0.6379 0.2610 1.1120 0.022 Uiso 1 1 calc R . . . .
C20 C 0.2210(3) 0.74943(17) 0.5780(2) 0.0189(6) Uani 1 1 d . . . . .
H20A H 0.1906 0.8014 0.5383 0.028 Uiso 1 1 calc GR . . . .
H20B H 0.2596 0.7585 0.6633 0.028 Uiso 1 1 calc GR . . . .
H20C H 0.1466 0.7120 0.5618 0.028 Uiso 1 1 calc GR . . . .
C1A C 0.5121(3) 0.41006(16) 0.6889(2) 0.0148(5) Uani 1 1 d . . . . .
C10A C 0.3815(3) 0.35493(16) 0.4948(2) 0.0172(5) Uani 1 1 d . . . . .
H10A H 0.4626 0.3475 0.4818 0.021 Uiso 1 1 calc R . . . .
C13 C 0.7359(3) 0.60234(17) 0.1969(2) 0.0160(5) Uani 1 1 d . . . . .
H13 H 0.7944 0.5809 0.1607 0.019 Uiso 1 1 calc R . . . .
C7 C 1.0696(3) 0.62117(17) 0.7988(3) 0.0180(5) Uani 1 1 d . . . . .
H7 H 1.1535 0.6107 0.7931 0.022 Uiso 1 1 calc R . . . .
C10 C 0.8249(3) 0.65176(16) 0.8168(2) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.7416 0.6631 0.8233 0.020 Uiso 1 1 calc R . . . .
C3A C 0.7543(3) 0.44370(16) 0.8512(2) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.7059(2) 0.55906(16) 0.2837(2) 0.0143(5) Uani 1 1 d . . . . .
C3 C 0.4628(3) 0.56485(17) 0.4521(2) 0.0147(5) Uani 1 1 d . . . . .
C11A C 0.5982(3) 0.43432(17) 0.9675(2) 0.0147(5) Uani 1 1 d . . . . .
C9 C 0.9370(3) 0.66972(18) 0.9109(2) 0.0182(5) Uani 1 1 d . . . . .
H9 H 0.9310 0.6933 0.9810 0.022 Uiso 1 1 calc R . . . .
C11 C 0.6185(3) 0.58834(16) 0.3373(2) 0.0146(5) Uani 1 1 d . . . . .
C13A C 0.4693(3) 0.42860(19) 1.0990(2) 0.0179(5) Uani 1 1 d . . . . .
H13A H 0.4104 0.4535 1.1318 0.021 Uiso 1 1 calc R . . . .
C6 C 0.9561(3) 0.60504(17) 0.7045(2) 0.0160(5) Uani 1 1 d . . . . .
C9A C 0.2665(3) 0.33148(17) 0.4077(2) 0.0181(6) Uani 1 1 d . . . . .
H9A H 0.2682 0.3081 0.3361 0.022 Uiso 1 1 calc R . . . .
C12A C 0.5092(3) 0.46826(17) 1.0154(2) 0.0163(5) Uani 1 1 d . . . . .
C4A C 0.7337(3) 0.39063(16) 0.7612(2) 0.0151(5) Uani 1 1 d . . . . .
C2A C 0.6351(3) 0.47848(16) 0.8723(2) 0.0147(5) Uani 1 1 d . . . . .
H2AB H 0.6530 0.5368 0.8960 0.018 Uiso 1 1 calc R . . . .
C8 C 1.0581(3) 0.65269(16) 0.9011(2) 0.0172(5) Uani 1 1 d . . . . .
C14 C 0.6777(3) 0.67779(17) 0.1649(2) 0.0164(5) Uani 1 1 d . . . . .
C17 C 0.3375(3) 0.53895(16) 0.3659(2) 0.0152(5) Uani 1 1 d . . . . .
C16A C 0.6456(3) 0.35692(17) 1.0056(2) 0.0170(5) Uani 1 1 d . . . . .
H16A H 0.7067 0.3325 0.9748 0.020 Uiso 1 1 calc R . . . .
C6A C 0.2604(3) 0.39675(16) 0.6185(2) 0.0157(5) Uani 1 1 d . . . . .
C8A C 0.1488(3) 0.34280(16) 0.4272(2) 0.0168(5) Uani 1 1 d . . . . .
C18 C 0.1072(3) 0.54193(18) 0.3060(3) 0.0206(6) Uani 1 1 d . . . . .
H18A H 0.0980 0.5711 0.2327 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.0361 0.5580 0.3347 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.1026 0.4832 0.2912 0.031 Uiso 1 1 calc GR . . . .
C14A C 0.5186(3) 0.35109(18) 1.1332(2) 0.0181(5) Uani 1 1 d . . . . .
C18A C 1.1104(3) 0.4375(2) 1.0078(3) 0.0252(6) Uani 1 1 d . . . . .
H18D H 1.1766 0.4100 0.9824 0.038 Uiso 1 1 calc GR . . . .
H18E H 1.1076 0.4125 1.0808 0.038 Uiso 1 1 calc GR . . . .
H18F H 1.1331 0.4952 1.0218 0.038 Uiso 1 1 calc GR . . . .
C20A C 0.9879(3) 0.25019(19) 0.7332(3) 0.0243(6) Uani 1 1 d . . . . .
H20D H 0.9506 0.2321 0.6510 0.036 Uiso 1 1 calc GR . . . .
H20E H 1.0257 0.2035 0.7838 0.036 Uiso 1 1 calc GR . . . .
H20F H 1.0566 0.2907 0.7401 0.036 Uiso 1 1 calc GR . . . .
H2 H 0.755(4) 0.507(3) 0.554(3) 0.027(10) Uiso 1 1 d . . . . .
H2AA H 0.465(4) 0.507(2) 0.749(3) 0.025(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C12 1.741(3) . ?
Cl2A C8A 1.739(3) . ?
Cl1 C8 1.738(3) . ?
Cl2 C6 1.744(3) . ?
Cl3A C12A 1.742(3) . ?
Cl1A C6A 1.741(3) . ?
Cl4 C14 1.738(3) . ?
Cl4A C14A 1.736(3) . ?
O3A C19A 1.215(3) . ?
O4 C19 1.326(3) . ?
O4 C20 1.451(3) . ?
O3 C19 1.209(3) . ?
O4A C19A 1.323(3) . ?
O4A C20A 1.448(3) . ?
O2 C17 1.347(3) . ?
O2 C18 1.444(3) . ?
O1A C17A 1.213(4) . ?
O1 C17 1.208(4) . ?
O2A C17A 1.340(3) . ?
O2A C18A 1.441(3) . ?
N1A C1A 1.317(4) . ?
N1A C4A 1.384(4) . ?
N2 C1 1.341(4) . ?
N2 C2 1.473(3) . ?
N2A C1A 1.342(4) . ?
N2A C2A 1.471(3) . ?
N1 C1 1.318(4) . ?
N1 C4 1.385(4) . ?
C5 C1 1.485(4) . ?
C5 C10 1.405(4) . ?
C5 C6 1.407(4) . ?
C17A C3A 1.475(4) . ?
C19A C4A 1.508(4) . ?
C19 C4 1.512(4) . ?
C4 C3 1.354(4) . ?
C2 C3 1.510(4) . ?
C2 C11 1.528(4) . ?
C5A C1A 1.485(4) . ?
C5A C10A 1.399(4) . ?
C5A C6A 1.406(4) . ?
C7A C6A 1.386(4) . ?
C7A C8A 1.390(4) . ?
C16 C15 1.386(4) . ?
C16 C11 1.392(4) . ?
C15 C14 1.390(4) . ?
C15A C16A 1.395(4) . ?
C15A C14A 1.381(4) . ?
C10A C9A 1.384(4) . ?
C13 C12 1.390(4) . ?
C13 C14 1.386(4) . ?
C7 C6 1.387(4) . ?
C7 C8 1.380(4) . ?
C10 C9 1.383(4) . ?
C3A C4A 1.350(4) . ?
C3A C2A 1.509(3) . ?
C12 C11 1.398(4) . ?
C3 C17 1.465(4) . ?
C11A C12A 1.396(4) . ?
C11A C2A 1.520(4) . ?
C11A C16A 1.390(4) . ?
C9 C8 1.384(4) . ?
C13A C12A 1.385(4) . ?
C13A C14A 1.389(4) . ?
C9A C8A 1.384(4) . ?

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
C19 O4 C20 114.6(2) . . ?
C19A O4A C20A 115.2(2) . . ?
C17 O2 C18 114.6(2) . . ?
C17A O2A C18A 116.3(2) . . ?
C1A N1A C4A 115.2(2) . . ?
C1 N2 C2 119.8(2) . . ?
C1A N2A C2A 119.7(2) . . ?
C1 N1 C4 115.1(2) . . ?
C10 C5 C1 116.5(2) . . ?
C10 C5 C6 116.8(3) . . ?
C6 C5 C1 126.7(2) . . ?
O1A C17A O2A 123.9(2) . . ?
O1A C17A C3A 123.1(3) . . ?
O2A C17A C3A 113.0(2) . . ?
O3A C19A O4A 125.4(3) . . ?
O3A C19A C4A 122.0(2) . . ?
O4A C19A C4A 112.5(2) . . ?
N2 C1 C5 120.1(2) . . ?
N1 C1 N2 122.8(2) . . ?
N1 C1 C5 117.0(2) . . ?
O4 C19 C4 112.2(2) . . ?
O3 C19 O4 124.9(2) . . ?
O3 C19 C4 122.8(2) . . ?
N1 C4 C19 110.5(2) . . ?
C3 C4 N1 125.0(2) . . ?
C3 C4 C19 124.3(2) . . ?
N2 C2 C3 107.2(2) . . ?
N2 C2 C11 110.9(2) . . ?
C3 C2 C11 113.8(2) . . ?
C10A C5A C1A 117.0(2) . . ?
C10A C5A C6A 117.1(2) . . ?
C6A C5A C1A 125.8(2) . . ?
C6A C7A C8A 118.2(2) . . ?
C15 C16 C11 122.2(2) . . ?
C16 C15 C14 118.4(3) . . ?
C14A C15A C16A 118.5(3) . . ?
N1A C1A N2A 122.8(2) . . ?
N1A C1A C5A 116.5(2) . . ?
N2A C1A C5A 120.6(2) . . ?
C9A C10A C5A 122.1(3) . . ?
C14 C13 C12 117.8(2) . . ?
C8 C7 C6 118.7(3) . . ?
C9 C10 C5 122.1(3) . . ?
C17A C3A C2A 116.1(2) . . ?
C4A C3A C17A 126.0(2) . . ?
C4A C3A C2A 117.5(2) . . ?
C13 C12 Cl3 117.1(2) . . ?
C13 C12 C11 122.5(3) . . ?
C11 C12 Cl3 120.4(2) . . ?
C4 C3 C2 116.8(2) . . ?
C4 C3 C17 126.9(2) . . ?
C17 C3 C2 116.1(2) . . ?
C12A C11A C2A 121.0(2) . . ?
C16A C11A C12A 117.3(2) . . ?
C16A C11A C2A 121.6(2) . . ?
C10 C9 C8 118.7(3) . . ?
C16 C11 C2 122.4(2) . . ?
C16 C11 C12 117.1(2) . . ?
C12 C11 C2 120.5(2) . . ?
C12A C13A C14A 117.7(2) . . ?
C5 C6 Cl2 122.2(2) . . ?
C7 C6 Cl2 115.9(2) . . ?
C7 C6 C5 121.9(3) . . ?
C10A C9A C8A 118.6(3) . . ?
C11A C12A Cl3A 119.8(2) . . ?
C13A C12A Cl3A 117.5(2) . . ?
C13A C12A C11A 122.7(3) . . ?
N1A C4A C19A 110.7(2) . . ?
C3A C4A N1A 124.9(2) . . ?
C3A C4A C19A 124.3(2) . . ?
N2A C2A C3A 107.2(2) . . ?
N2A C2A C11A 110.3(2) . . ?
C3A C2A C11A 113.8(2) . . ?
C7 C8 Cl1 120.0(2) . . ?
C7 C8 C9 121.7(3) . . ?
C9 C8 Cl1 118.2(2) . . ?
C15 C14 Cl4 119.3(2) . . ?
C13 C14 Cl4 118.7(2) . . ?
C13 C14 C15 121.9(3) . . ?
O2 C17 C3 113.7(2) . . ?
O1 C17 O2 123.3(3) . . ?
O1 C17 C3 123.0(2) . . ?
C11A C16A C15A 121.8(3) . . ?
C5A C6A Cl1A 122.0(2) . . ?
C7A C6A Cl1A 115.9(2) . . ?
C7A C6A C5A 122.0(2) . . ?
C7A C8A Cl2A 119.4(2) . . ?
C9A C8A Cl2A 118.6(2) . . ?
C9A C8A C7A 122.0(3) . . ?
C15A C14A Cl4A 119.2(2) . . ?
C15A C14A C13A 122.0(3) . . ?
C13A C14A Cl4A 118.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.314
_oxdiff_exptl_absorpt_empirical_full_min 0.853
