# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ev2029
_database_code_depnum_ccdc_archive 'CCDC 1959807'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3, C H2 Cl2'
_chemical_formula_sum            'C21 H23 Cl2 N O3'
_chemical_formula_weight         408.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 N1 O3'
_chemical_oxdiff_usercomment     SLL-2
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'
Cl Cl 0.1484 0.1585 '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      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                   8.9486(5)
_cell_length_b                   9.5948(4)
_cell_length_c                   12.8823(6)
_cell_angle_alpha                82.687(4)
_cell_angle_beta                 71.563(4)
_cell_angle_gamma                87.665(4)
_cell_volume                     1040.77(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.1090
_cell_measurement_theta_min      2.5020
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21373
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.399
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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    -20.00  25.00   1.00   20.00    --  -17.15 -99.00-150.00   45
  2  ω    -93.00 -35.00   1.00   20.00    --  -17.15-178.00   0.00   58
  3  ω    -20.00  25.00   1.00   20.00    --  -17.15 -99.00  60.00   45
  4  ω     -7.00  91.00   1.00   20.00    --   18.79  38.00  60.00   98
  5  ω     35.00  95.00   1.00   20.00    --   18.79 178.00 -90.00   60
  6  ω    -50.00  39.00   1.00   20.00    --   18.79 -57.00 -60.00   89
  7  ω    -54.00  44.00   1.00   20.00    --   18.79 -38.00-120.00   98
  8  ω    -20.00  25.00   1.00   20.00    --  -17.15 -99.00 -90.00   45
  9  ω    -20.00  25.00   1.00   20.00    --  -17.15 -99.00 120.00   45
 10  ω    -20.00  61.00   1.00   20.00    --   18.79 -99.00  90.00   81
 11  ω     -3.00  88.00   1.00   20.00    --   18.79  57.00 -30.00   91
 12  ω    -20.00  61.00   1.00   20.00    --   18.79 -99.00-120.00   81
 13  ω    -25.00  92.00   1.00   20.00    --   18.79  19.00 -60.00  117
 14  ω     -3.00  84.00   1.00   20.00    --   18.79  57.00 150.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0547241000
_diffrn_orient_matrix_UB_12      -0.0285693000
_diffrn_orient_matrix_UB_13      0.0505762000
_diffrn_orient_matrix_UB_21      0.0630556000
_diffrn_orient_matrix_UB_22      -0.0280369000
_diffrn_orient_matrix_UB_23      0.0184173000
_diffrn_orient_matrix_UB_31      0.0032010000
_diffrn_orient_matrix_UB_32      0.0628709000
_diffrn_orient_matrix_UB_33      0.0228294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3015
_reflns_number_total             4239
_reflns_odcompleteness_completeness 99.88
_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 1.171.39.46 (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         0.342
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.049
_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)+(0.0766P)²+0.5873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.1897
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O18(H18)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.3630(3) 0.2761(2) 0.41879(18) 0.0556(5) Uani 1 1 d . . . . .
H1 H 0.418(3) 0.199(3) 0.394(2) 0.067 Uiso 1 1 d R . . . .
C2 C 0.2615(3) 0.2622(2) 0.5228(2) 0.0543(6) Uani 1 1 d . . . . .
C3 C 0.1867(3) 0.3905(2) 0.56168(19) 0.0493(5) Uani 1 1 d . . . . .
C4 C 0.0814(3) 0.3862(3) 0.6689(2) 0.0572(6) Uani 1 1 d . . . . .
H4 H 0.060884 0.300898 0.713971 0.069 Uiso 1 1 calc R . . . .
C5 C 0.0087(3) 0.5049(3) 0.7081(2) 0.0597(6) Uani 1 1 d . . . . .
H5 H -0.061096 0.500598 0.779426 0.072 Uiso 1 1 calc R . . . .
C6 C 0.0397(3) 0.6335(3) 0.6404(2) 0.0546(6) Uani 1 1 d . . . . .
C7 C 0.1420(3) 0.6409(2) 0.53454(19) 0.0507(5) Uani 1 1 d . . . . .
H7 H 0.161289 0.726971 0.490433 0.061 Uiso 1 1 calc R . . . .
C8 C 0.2175(3) 0.5190(2) 0.49257(19) 0.0469(5) Uani 1 1 d . . . . .
C9 C 0.3226(3) 0.5222(2) 0.38061(19) 0.0479(5) Uani 1 1 d . . . . .
C10 C 0.3921(3) 0.4003(2) 0.34737(19) 0.0491(5) Uani 1 1 d . . . . .
O11 O 0.2369(2) 0.14466(18) 0.57844(16) 0.0705(5) Uani 1 1 d . . . . .
O12 O -0.0384(2) 0.7461(2) 0.68741(16) 0.0700(5) Uani 1 1 d . . . . .
C13 C -0.0126(4) 0.8803(3) 0.6218(3) 0.0837(9) Uani 1 1 d . . . . .
H13A H -0.037574 0.875030 0.555205 0.125 Uiso 1 1 calc GR . . . .
H13B H 0.095778 0.906712 0.603755 0.125 Uiso 1 1 calc GR . . . .
H13C H -0.078795 0.949174 0.662457 0.125 Uiso 1 1 calc GR . . . .
C14 C 0.3506(3) 0.6572(2) 0.30278(19) 0.0505(5) Uani 1 1 d . . . . .
H14A H 0.251011 0.706426 0.313331 0.061 Uiso 1 1 calc R . . . .
H14B H 0.386265 0.633872 0.227718 0.061 Uiso 1 1 calc R . . . .
C15 C 0.4698(3) 0.7562(2) 0.3164(2) 0.0518(6) Uani 1 1 d . . . . .
H15A H 0.439662 0.773954 0.392740 0.062 Uiso 1 1 calc R . . . .
H15B H 0.572380 0.711152 0.298714 0.062 Uiso 1 1 calc R . . . .
C16 C 0.4820(3) 0.8954(3) 0.2431(2) 0.0609(6) Uani 1 1 d . . . . .
H16A H 0.506545 0.876365 0.167338 0.073 Uiso 1 1 calc R . . . .
H16B H 0.380058 0.941306 0.263203 0.073 Uiso 1 1 calc R . . . .
C17 C 0.6033(4) 0.9949(3) 0.2492(2) 0.0699(8) Uani 1 1 d . . . . .
H17A H 0.704783 0.948128 0.233097 0.084 Uiso 1 1 calc R . . . .
H17B H 0.612023 1.075147 0.193651 0.084 Uiso 1 1 calc R . . . .
O18 O 0.5652(3) 1.0427(2) 0.35445(19) 0.0824(7) Uani 1 1 d . . . . .
H18 H 0.610(5) 0.994(4) 0.392(2) 0.124 Uiso 1 1 calc GR . . . .
C19 C 0.4983(3) 0.3846(2) 0.2347(2) 0.0534(6) Uani 1 1 d . . . . .
C20 C 0.4410(4) 0.3367(4) 0.1583(2) 0.0765(8) Uani 1 1 d . . . . .
H20 H 0.334538 0.315295 0.177402 0.092 Uiso 1 1 calc R . . . .
C21 C 0.5387(5) 0.3202(4) 0.0544(3) 0.0916(10) Uani 1 1 d . . . . .
H21 H 0.497894 0.288251 0.003667 0.110 Uiso 1 1 calc R . . . .
C22 C 0.6939(5) 0.3499(4) 0.0253(3) 0.0941(12) Uani 1 1 d . . . . .
H22 H 0.760025 0.338420 -0.045094 0.113 Uiso 1 1 calc R . . . .
C23 C 0.7528(4) 0.3971(4) 0.1003(4) 0.1092(14) Uani 1 1 d . . . . .
H23 H 0.859448 0.417955 0.080558 0.131 Uiso 1 1 calc R . . . .
C24 C 0.6552(4) 0.4141(4) 0.2052(3) 0.0879(10) Uani 1 1 d . . . . .
H24 H 0.696555 0.445674 0.255783 0.105 Uiso 1 1 calc R . . . .
C25 C 0.9371(7) 0.8622(5) -0.0768(4) 0.1348(18) Uani 1 1 d . . . . .
H25A H 0.956379 0.813062 -0.141157 0.162 Uiso 1 1 calc R . . . .
H25B H 1.037921 0.893025 -0.074855 0.162 Uiso 1 1 calc R . . . .
Cl26 Cl 0.8546(2) 0.75067(19) 0.03674(16) 0.1872(9) Uani 1 1 d . . . . .
Cl27 Cl 0.8210(3) 1.00754(19) -0.08943(17) 0.1935(9) 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
N1 H1 0.91(3) . ?
N1 C2 1.354(3) . ?
N1 C10 1.389(3) . ?
C2 C3 1.447(4) . ?
C2 O11 1.244(3) . ?
C3 C4 1.401(3) . ?
C3 C8 1.408(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(3) . ?
C6 C7 1.376(3) . ?
C6 O12 1.364(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.408(3) . ?
C8 C9 1.449(3) . ?
C9 C10 1.355(3) . ?
C9 C14 1.511(3) . ?
C10 C19 1.485(3) . ?
O12 C13 1.432(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.521(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.501(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 O18 1.420(3) . ?
O18 H18 0.82(4) . ?
C19 C20 1.377(4) . ?
C19 C24 1.365(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.351(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(5) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 Cl26 1.677(6) . ?
C25 Cl27 1.727(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 118.1(18) . . ?
C2 N1 C10 125.1(2) . . ?
C10 N1 H1 116.9(18) . . ?
N1 C2 C3 115.6(2) . . ?
O11 C2 N1 120.3(2) . . ?
O11 C2 C3 124.1(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 C8 119.8(2) . . ?
C8 C3 C2 120.7(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.7(2) . . ?
O12 C6 C5 115.0(2) . . ?
O12 C6 C7 124.3(2) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 118.4(2) . . ?
C3 C8 C9 119.6(2) . . ?
C7 C8 C9 122.0(2) . . ?
C8 C9 C14 120.7(2) . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 C14 121.2(2) . . ?
N1 C10 C19 114.3(2) . . ?
C9 C10 N1 120.8(2) . . ?
C9 C10 C19 124.9(2) . . ?
C6 O12 C13 117.6(2) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 108.5 . . ?
C9 C14 H14B 108.5 . . ?
C9 C14 C15 114.99(19) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.5(2) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 114.9(2) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
O18 C17 C16 112.3(2) . . ?
O18 C17 H17A 109.1 . . ?
O18 C17 H17B 109.1 . . ?
C17 O18 H18 109.5 . . ?
C20 C19 C10 120.5(2) . . ?
C24 C19 C10 120.9(3) . . ?
C24 C19 C20 118.5(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.1(3) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
H25A C25 H25B 107.8 . . ?
Cl26 C25 H25A 109.0 . . ?
Cl26 C25 H25B 109.0 . . ?
Cl26 C25 Cl27 112.8(3) . . ?
Cl27 C25 H25A 109.0 . . ?
Cl27 C25 H25B 109.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O18_$1 0.91(3) 1.96(3) 2.859(3) 169(3) 1_545
O18 H18 O11_$2 0.82 1.96 2.725(3) 156.3 2_666

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
N1 C2 C3 C4 -179.2(2) . . . . ?
N1 C2 C3 C8 1.4(3) . . . . ?
N1 C10 C19 C20 81.1(3) . . . . ?
N1 C10 C19 C24 -97.4(3) . . . . ?
C2 N1 C10 C9 3.0(4) . . . . ?
C2 N1 C10 C19 -175.0(2) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
C2 C3 C8 C7 -179.9(2) . . . . ?
C2 C3 C8 C9 1.3(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C8 C9 C10 -2.1(3) . . . . ?
C3 C8 C9 C14 176.59(19) . . . . ?
C4 C3 C8 C7 0.8(3) . . . . ?
C4 C3 C8 C9 -178.0(2) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C6 O12 -179.8(2) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C5 C6 O12 C13 -179.4(2) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C6 C7 C8 C9 178.3(2) . . . . ?
C7 C6 O12 C13 0.4(4) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
C7 C8 C9 C14 -2.2(3) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C8 C9 C10 N1 0.1(3) . . . . ?
C8 C9 C10 C19 177.9(2) . . . . ?
C8 C9 C14 C15 81.1(3) . . . . ?
C9 C10 C19 C20 -96.9(3) . . . . ?
C9 C10 C19 C24 84.6(3) . . . . ?
C9 C14 C15 C16 -174.9(2) . . . . ?
C10 N1 C2 C3 -3.7(3) . . . . ?
C10 N1 C2 O11 176.0(2) . . . . ?
C10 C9 C14 C15 -100.3(3) . . . . ?
C10 C19 C20 C21 -179.2(3) . . . . ?
C10 C19 C24 C23 179.2(3) . . . . ?
O11 C2 C3 C4 1.1(4) . . . . ?
O11 C2 C3 C8 -178.3(2) . . . . ?
O12 C6 C7 C8 -179.9(2) . . . . ?
C14 C9 C10 N1 -178.6(2) . . . . ?
C14 C9 C10 C19 -0.8(3) . . . . ?
C14 C15 C16 C17 -177.4(2) . . . . ?
C15 C16 C17 O18 -65.9(3) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C20 C19 C24 C23 0.6(5) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C22 C23 C24 C19 -0.4(6) . . . . ?
C24 C19 C20 C21 -0.6(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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.570
