# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_p20210630a
_database_code_depnum_ccdc_archive 'CCDC 2101275'
loop_
_audit_author_name
_audit_author_address
'Lv Jie'
;Chinese academy of medical science
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_audit_creation_date             2021-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C21 H20 N O6'
_chemical_formula_sum            'C21 H20 Cl N O6'
_chemical_formula_weight         417.83
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.64130(10)
_cell_length_b                   12.87260(10)
_cell_length_c                   25.5684(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3831.52(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8820
_cell_measurement_theta_min      5.0940
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19537
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         87.150
_diffrn_reflns_theta_min         3.457
_diffrn_ambient_temperature      294.15
_diffrn_detector                 pilatus
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  94.00   0.50    2.50    --    5.00  51.00 101.00  238
  2  ω    -84.00  35.00   0.50    2.50    --    5.00 -51.00 -44.00  238
  3  ω   -138.00 -18.00   0.50    2.50    --  -48.80 -51.00 -44.00  240
  4  ω    -79.00  41.00   0.50    2.50    --  -48.80  51.00 101.00  240
  5  ω   -199.00 -80.00   0.50    5.50    -- -110.00 -51.00 -44.00  238
  6  ω   -140.00 -21.00   0.50    5.50    -- -110.00  51.00 101.00  238
  7  ω    -79.00  41.00   0.50    2.50    --  -48.80  57.00-180.00  240
  8  ω   -138.00 -18.00   0.50    2.50    --  -48.80 -57.00   0.00  240
  9  ω   -168.00 -21.00   0.50    5.50    -- -110.00  19.00 -30.00  294
 10  ω   -144.00 -21.00   0.50    5.50    -- -110.00  72.00 -30.00  246
 11  ω   -140.00 -21.00   0.50    5.50    -- -110.00  57.00 -30.00  238
 12  ω   -199.00 -52.00   0.50    5.50    -- -110.00 -19.00 -30.00  294
 13  ω   -144.00 -21.00   0.50    5.50    -- -110.00  72.00  90.00  246
 14  ω   -199.00 -77.00   0.50    5.50    -- -110.00 -38.00  90.00  244
 15  ω   -199.00 -80.00   0.50    5.50    -- -110.00 -57.00-180.00  238
 16  ω    -98.00 -62.00   0.50    5.50    -- -110.00  38.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1104166000
_diffrn_orient_matrix_UB_12      0.0016357000
_diffrn_orient_matrix_UB_13      0.0332454000
_diffrn_orient_matrix_UB_21      -0.0243133000
_diffrn_orient_matrix_UB_22      -0.1119408000
_diffrn_orient_matrix_UB_23      0.0181827000
_diffrn_orient_matrix_UB_31      0.0687540000
_diffrn_orient_matrix_UB_32      -0.0423371000
_diffrn_orient_matrix_UB_33      -0.0468325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3753
_reflns_number_total             4122
_reflns_odcompleteness_completeness 99.82
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.183
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_coef       0.00056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.195
_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)+(0.0236P)²+5.5103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1225
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C5(H5), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B),
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C18(H18)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.86691(14) 0.500000 0.500000 0.0696(5) Uani 1 2 d S T P . .
Cl2 Cl 1.000000 0.97062(12) 0.250000 0.0650(5) Uani 1 2 d S T P . .
O1 O 0.2197(4) 0.6148(4) 0.46832(18) 0.0942(15) Uani 1 1 d . . . . .
O2 O 0.2284(3) 0.4739(4) 0.41288(17) 0.0859(13) Uani 1 1 d . . . . .
O3 O 0.9523(4) 0.7497(3) 0.34315(16) 0.0758(11) Uani 1 1 d . . . . .
O4 O 0.8674(3) 0.7716(3) 0.26582(15) 0.0650(10) Uani 1 1 d . . . . .
H4 H 0.903915 0.826074 0.265681 0.097 Uiso 1 1 calc GR . . . .
O5 O 1.0634(3) 0.4669(3) 0.31604(14) 0.0610(9) Uani 1 1 d . . . . .
O6 O 1.1025(3) 0.2928(3) 0.29997(16) 0.0701(10) Uani 1 1 d . . . . .
N1 N 0.7492(3) 0.5677(3) 0.39724(14) 0.0435(8) Uani 1 1 d . . . . .
H1 H 0.772859 0.536257 0.430431 0.052 Uiso 1 1 calc R . . . .
C1 C 0.1524(5) 0.5500(6) 0.4347(3) 0.093(2) Uani 1 1 d . . . . .
H1A H 0.117675 0.591122 0.407143 0.111 Uiso 1 1 calc R . . . .
H1B H 0.091749 0.516352 0.454448 0.111 Uiso 1 1 calc R . . . .
C2 C 0.3374(4) 0.5165(5) 0.4189(2) 0.0624(13) Uani 1 1 d . . . . .
C3 C 0.4364(4) 0.4845(4) 0.39607(19) 0.0552(11) Uani 1 1 d . . . . .
H3 H 0.438186 0.428040 0.373395 0.066 Uiso 1 1 calc R . . . .
C4 C 0.5368(4) 0.5412(3) 0.40844(18) 0.0480(10) Uani 1 1 d . . . . .
C5 C 0.6444(3) 0.5089(3) 0.37897(17) 0.0446(9) Uani 1 1 d . . . . .
H5 H 0.632678 0.524627 0.341848 0.053 Uiso 1 1 calc R . . . .
C6 C 0.6714(4) 0.3939(3) 0.3838(2) 0.0560(12) Uani 1 1 d . . . . .
H6A H 0.673529 0.375370 0.420607 0.067 Uiso 1 1 calc R . . . .
H6B H 0.610092 0.354345 0.367601 0.067 Uiso 1 1 calc R . . . .
C7 C 0.7840(4) 0.3639(3) 0.35891(19) 0.0510(10) Uani 1 1 d . . . . .
C8 C 0.8059(5) 0.2606(4) 0.3456(2) 0.0589(12) Uani 1 1 d . . . . .
H8 H 0.748225 0.211511 0.350414 0.071 Uiso 1 1 calc R . . . .
C9 C 0.9117(5) 0.2284(4) 0.3252(2) 0.0641(14) Uani 1 1 d . . . . .
H9 H 0.925956 0.159454 0.316520 0.077 Uiso 1 1 calc R . . . .
C10 C 0.9924(4) 0.3036(3) 0.31880(18) 0.0543(11) Uani 1 1 d . . . . .
C11 C 1.1504(5) 0.3952(4) 0.2995(2) 0.0636(13) Uani 1 1 d . . . . .
H11A H 1.176202 0.412616 0.264483 0.076 Uiso 1 1 calc R . . . .
H11B H 1.215778 0.398617 0.322893 0.076 Uiso 1 1 calc R . . . .
C12 C 0.9710(4) 0.4063(3) 0.33007(18) 0.0509(11) Uani 1 1 d . . . . .
C13 C 0.8677(4) 0.4397(3) 0.35009(17) 0.0455(10) Uani 1 1 d . . . . .
C14 C 0.8488(4) 0.5542(3) 0.35951(17) 0.0434(9) Uani 1 1 d . . . . .
H14 H 0.917731 0.581069 0.376852 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7245(4) 0.6800(3) 0.40836(18) 0.0505(11) Uani 1 1 d . . . . .
H15A H 0.692821 0.712904 0.377448 0.061 Uiso 1 1 calc R . . . .
H15B H 0.795130 0.715591 0.417563 0.061 Uiso 1 1 calc R . . . .
C16 C 0.6399(5) 0.6874(4) 0.4530(2) 0.0604(12) Uani 1 1 d . . . . .
H16A H 0.619312 0.759640 0.458497 0.072 Uiso 1 1 calc R . . . .
H16B H 0.675608 0.661938 0.484778 0.072 Uiso 1 1 calc R . . . .
C17 C 0.5323(4) 0.6250(4) 0.44197(18) 0.0538(11) Uani 1 1 d . . . . .
C18 C 0.4277(5) 0.6543(5) 0.4652(2) 0.0677(14) Uani 1 1 d . . . . .
H18 H 0.423957 0.709633 0.488534 0.081 Uiso 1 1 calc R . . . .
C19 C 0.3324(5) 0.5991(5) 0.4525(2) 0.0684(15) Uani 1 1 d . . . . .
C20 C 0.8347(4) 0.6140(3) 0.30838(17) 0.0461(10) Uani 1 1 d . . . . .
H20A H 0.866929 0.573091 0.280108 0.055 Uiso 1 1 calc R . . . .
H20B H 0.753379 0.622878 0.301364 0.055 Uiso 1 1 calc R . . . .
C21 C 0.8913(4) 0.7190(3) 0.3087(2) 0.0496(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.431(8) . ?
O1 C19 1.388(7) . ?
O2 C1 1.433(8) . ?
O2 C2 1.391(6) . ?
O3 C21 1.199(6) . ?
O4 H4 0.8200 . ?
O4 C21 1.318(6) . ?
O5 C11 1.435(6) . ?
O5 C12 1.376(6) . ?
O6 C10 1.376(6) . ?
O6 C11 1.431(7) . ?
N1 H1 0.9800 . ?
N1 C5 1.509(5) . ?
N1 C14 1.518(5) . ?
N1 C15 1.500(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.356(7) . ?
C2 C19 1.368(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(6) . ?
C4 C5 1.519(6) . ?
C4 C17 1.379(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.519(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.508(7) . ?
C7 C8 1.396(6) . ?
C7 C13 1.396(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(7) . ?
C10 C12 1.375(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.376(6) . ?
C13 C14 1.510(5) . ?
C14 H14 0.9800 . ?
C14 C20 1.526(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.511(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(7) . ?
C17 C18 1.407(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.504(6) . ?

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 O1 C1 104.9(5) . . ?
C2 O2 C1 104.5(5) . . ?
C21 O4 H4 109.5 . . ?
C12 O5 C11 105.3(4) . . ?
C10 O6 C11 105.8(4) . . ?
C5 N1 H1 106.7 . . ?
C5 N1 C14 111.3(3) . . ?
C14 N1 H1 106.7 . . ?
C15 N1 H1 106.7 . . ?
C15 N1 C5 112.8(3) . . ?
C15 N1 C14 112.2(3) . . ?
O1 C1 O2 107.1(5) . . ?
O1 C1 H1A 110.3 . . ?
O1 C1 H1B 110.3 . . ?
O2 C1 H1A 110.3 . . ?
O2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
C3 C2 O2 127.4(5) . . ?
C3 C2 C19 122.9(5) . . ?
C19 C2 O2 109.7(5) . . ?
C2 C3 H3 121.6 . . ?
C2 C3 C4 116.7(4) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 C5 115.4(4) . . ?
C17 C4 C3 120.8(4) . . ?
C17 C4 C5 123.6(4) . . ?
N1 C5 C4 112.1(3) . . ?
N1 C5 H5 108.0 . . ?
N1 C5 C6 107.2(3) . . ?
C4 C5 H5 108.0 . . ?
C6 C5 C4 113.4(4) . . ?
C6 C5 H5 108.0 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.2(4) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C8 C7 C6 120.3(4) . . ?
C13 C7 C6 119.7(4) . . ?
C13 C7 C8 119.9(5) . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.2(5) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 121.9 . . ?
C10 C9 C8 116.3(4) . . ?
C10 C9 H9 121.9 . . ?
C9 C10 O6 127.9(4) . . ?
C9 C10 C12 122.3(5) . . ?
C12 C10 O6 109.8(4) . . ?
O5 C11 H11A 110.0 . . ?
O5 C11 H11B 110.0 . . ?
O6 C11 O5 108.4(4) . . ?
O6 C11 H11A 110.0 . . ?
O6 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C10 C12 O5 110.4(4) . . ?
C10 C12 C13 122.4(5) . . ?
C13 C12 O5 127.1(4) . . ?
C7 C13 C14 123.7(4) . . ?
C12 C13 C7 116.9(4) . . ?
C12 C13 C14 119.4(4) . . ?
N1 C14 H14 107.3 . . ?
N1 C14 C20 113.8(3) . . ?
C13 C14 N1 109.0(3) . . ?
C13 C14 H14 107.3 . . ?
C13 C14 C20 111.8(4) . . ?
C20 C14 H14 107.3 . . ?
N1 C15 H15A 109.8 . . ?
N1 C15 H15B 109.8 . . ?
N1 C15 C16 109.2(4) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C15 C16 C17 111.4(4) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C4 C17 C16 120.0(4) . . ?
C4 C17 C18 120.3(5) . . ?
C18 C17 C16 119.7(4) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 C17 117.8(5) . . ?
C19 C18 H18 121.1 . . ?
C2 C19 O1 109.7(5) . . ?
C18 C19 O1 128.8(5) . . ?
C18 C19 C2 121.5(5) . . ?
C14 C20 H20A 108.8 . . ?
C14 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C14 113.7(4) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
O3 C21 O4 124.6(4) . . ?
O3 C21 C20 124.0(4) . . ?
O4 C21 C20 111.4(4) . . ?

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
O2 C2 C3 C4 179.8(5) . . . . ?
O2 C2 C19 O1 -1.6(7) . . . . ?
O2 C2 C19 C18 179.8(6) . . . . ?
O5 C12 C13 C7 176.7(4) . . . . ?
O5 C12 C13 C14 -1.2(7) . . . . ?
O6 C10 C12 O5 3.7(6) . . . . ?
O6 C10 C12 C13 -179.3(4) . . . . ?
N1 C5 C6 C7 -50.3(5) . . . . ?
N1 C14 C20 C21 94.5(4) . . . . ?
N1 C15 C16 C17 -54.7(5) . . . . ?
C1 O1 C19 C2 -11.0(8) . . . . ?
C1 O1 C19 C18 167.6(7) . . . . ?
C1 O2 C2 C3 -166.6(6) . . . . ?
C1 O2 C2 C19 13.4(7) . . . . ?
C2 O2 C1 O1 -20.0(7) . . . . ?
C2 C3 C4 C5 -175.4(4) . . . . ?
C2 C3 C4 C17 -0.3(7) . . . . ?
C3 C2 C19 O1 178.4(5) . . . . ?
C3 C2 C19 C18 -0.3(10) . . . . ?
C3 C4 C5 N1 -175.8(4) . . . . ?
C3 C4 C5 C6 -54.3(5) . . . . ?
C3 C4 C17 C16 -177.5(5) . . . . ?
C3 C4 C17 C18 1.2(8) . . . . ?
C4 C5 C6 C7 -174.5(4) . . . . ?
C4 C17 C18 C19 -1.6(8) . . . . ?
C5 N1 C14 C13 -52.3(4) . . . . ?
C5 N1 C14 C20 73.2(4) . . . . ?
C5 N1 C15 C16 63.5(5) . . . . ?
C5 C4 C17 C16 -2.9(7) . . . . ?
C5 C4 C17 C18 175.8(5) . . . . ?
C5 C6 C7 C8 -160.4(4) . . . . ?
C5 C6 C7 C13 20.9(6) . . . . ?
C6 C7 C8 C9 -176.2(5) . . . . ?
C6 C7 C13 C12 176.3(4) . . . . ?
C6 C7 C13 C14 -5.9(7) . . . . ?
C7 C8 C9 C10 -0.3(8) . . . . ?
C7 C13 C14 N1 21.0(6) . . . . ?
C7 C13 C14 C20 -105.7(5) . . . . ?
C8 C7 C13 C12 -2.4(7) . . . . ?
C8 C7 C13 C14 175.4(4) . . . . ?
C8 C9 C10 O6 179.6(5) . . . . ?
C8 C9 C10 C12 -2.0(8) . . . . ?
C9 C10 C12 O5 -175.0(5) . . . . ?
C9 C10 C12 C13 2.0(8) . . . . ?
C10 O6 C11 O5 -2.9(5) . . . . ?
C10 C12 C13 C7 0.3(7) . . . . ?
C10 C12 C13 C14 -177.6(4) . . . . ?
C11 O5 C12 C10 -5.3(5) . . . . ?
C11 O5 C12 C13 177.9(5) . . . . ?
C11 O6 C10 C9 178.2(5) . . . . ?
C11 O6 C10 C12 -0.4(5) . . . . ?
C12 O5 C11 O6 5.0(5) . . . . ?
C12 C13 C14 N1 -161.3(4) . . . . ?
C12 C13 C14 C20 72.0(5) . . . . ?
C13 C7 C8 C9 2.5(8) . . . . ?
C13 C14 C20 C21 -141.5(4) . . . . ?
C14 N1 C5 C4 -166.4(3) . . . . ?
C14 N1 C5 C6 68.6(4) . . . . ?
C14 N1 C15 C16 -170.0(4) . . . . ?
C14 C20 C21 O3 7.6(7) . . . . ?
C14 C20 C21 O4 -173.8(4) . . . . ?
C15 N1 C5 C4 -39.4(5) . . . . ?
C15 N1 C5 C6 -164.4(4) . . . . ?
C15 N1 C14 C13 -179.7(4) . . . . ?
C15 N1 C14 C20 -54.1(4) . . . . ?
C15 C16 C17 C4 25.8(7) . . . . ?
C15 C16 C17 C18 -152.9(5) . . . . ?
C16 C17 C18 C19 177.2(5) . . . . ?
C17 C4 C5 N1 9.3(6) . . . . ?
C17 C4 C5 C6 130.9(5) . . . . ?
C17 C18 C19 O1 -177.3(6) . . . . ?
C17 C18 C19 C2 1.1(9) . . . . ?
C19 O1 C1 O2 19.1(8) . . . . ?
C19 C2 C3 C4 -0.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.573
