# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mh1142amoins
_database_code_depnum_ccdc_archive 'CCDC 1989155'
loop_
_audit_author_name
_audit_author_address
'sylvain MARQUE'
;university Aix MArseille
France
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2020-02-18
_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         'C23 H35 N O6'
_chemical_formula_sum            'C23 H35 N O6'
_chemical_formula_weight         421.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c23 h35 o6 n'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.11280(10)
_cell_length_b                   16.4599(3)
_cell_length_c                   12.1815(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.377(2)
_cell_angle_gamma                90
_cell_volume                     1209.28(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11653
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.9850
_cell_measurement_theta_min      4.5410
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84475
_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    1.158
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16331
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.180
_diffrn_reflns_theta_min         3.678
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    2.00    --  -41.07 -38.00 120.00   98
  2  ω    -66.00  33.00   1.00    2.00    --  -41.07  38.00 -60.00   99
  3  ω     23.00  97.00   1.00    2.00    --   41.07-125.00 150.00   74
  4  ω     17.00 115.00   1.00    2.00    --   41.07  38.00 -30.00   98
  5  ω    -33.00  66.00   1.00    2.00    --   41.07 -38.00  90.00   99
  6  ω     28.00 127.00   1.00   20.00    --  101.41 -45.00  60.00   99
  7  ω     23.00 111.00   1.00   20.00    --  101.41-106.00 106.00   88
  8  ω     25.00 134.00   1.00   20.00    --  101.41 -77.00 150.00  109
  9  ω     28.00 127.00   1.00   20.00    --  101.41 -45.00 -60.00   99
 10  ω     28.00 117.00   1.00   20.00    --  101.41-125.00 -30.00   89
 11  ω     25.00 130.00   1.00   20.00    --  101.41 -30.00 150.00  105
 12  ω     94.00 175.00   1.00   20.00    --  101.41 125.00 150.00   81
 13  ω     72.00 174.00   1.00   20.00    --  101.41  61.00 150.00  102
 14  ω     13.00 178.00   1.00   20.00    --  101.41   0.00   0.00  165
 15  ω   -117.00  -8.00   1.00    2.00    --  -41.07 -77.00  60.00  109
 16  ω   -117.00  -8.00   1.00    2.00    --  -41.07 -77.00 -30.00  109
 17  ω   -113.00 -13.00   1.00    2.00    --  -41.07 -57.00-150.00  100
 18  ω      1.00  82.00   1.00    2.00    --   41.07 -99.00   0.00   81
 19  ω     72.00 174.00   1.00   20.00    --  101.41  61.00-150.00  102
 20  ω     72.00 174.00   1.00   20.00    --  101.41  61.00  30.00  102
 21  ω     72.00 174.00   1.00   20.00    --  101.41  61.00  90.00  102
 22  ω     69.00 178.00   1.00   20.00    --  101.41  77.00 -90.00  109
 23  ω     69.00 178.00   1.00   20.00    --  101.41  77.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0229235000
_diffrn_orient_matrix_UB_12      0.0792873000
_diffrn_orient_matrix_UB_13      -0.0642727000
_diffrn_orient_matrix_UB_21      -0.2366707000
_diffrn_orient_matrix_UB_22      0.0246938000
_diffrn_orient_matrix_UB_23      0.0146207000
_diffrn_orient_matrix_UB_31      0.0935388000
_diffrn_orient_matrix_UB_32      0.0431463000
_diffrn_orient_matrix_UB_33      0.1099150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4457
_reflns_number_total             4598
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 2020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_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     277
_refine_ls_number_reflns         4598
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.059
_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)+(0.0789P)²+0.0334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.01798(19) 0.55106(9) 0.56677(11) 0.0446(3) Uani 1 1 d . . . . .
O2 O 0.1636(3) 0.40004(10) 0.67647(17) 0.0612(4) Uani 1 1 d . . . . .
O3 O 0.5021(2) 0.45295(9) 0.67620(13) 0.0500(3) Uani 1 1 d . . . . .
O4 O 0.2951(3) 0.55678(13) 0.84783(13) 0.0651(4) Uani 1 1 d . . . . .
O5 O 0.0767(5) 0.5313(2) 0.97450(19) 0.1033(9) Uani 1 1 d . . . . .
O6 O 0.0244(3) 0.64389(10) 0.75836(14) 0.0582(4) Uani 1 1 d . . . . .
N1 N 0.0938(2) 0.57159(10) 0.46192(13) 0.0443(4) Uani 1 1 d . . . . .
C1 C 0.1971(3) 0.54448(12) 0.65552(15) 0.0437(4) Uani 1 1 d . . . . .
H1 H 0.316813 0.581843 0.645072 0.052 Uiso 1 1 calc R . . . .
C2 C 0.2828(3) 0.45744(12) 0.67011(17) 0.0461(4) Uani 1 1 d . . . . .
C3 C 0.5986(4) 0.37154(14) 0.6902(2) 0.0549(5) Uani 1 1 d . . . . .
H3A H 0.740555 0.371709 0.664436 0.066 Uiso 1 1 calc R . . . .
H3B H 0.502271 0.333750 0.644124 0.066 Uiso 1 1 calc R . . . .
C4 C 0.6314(4) 0.34249(13) 0.8083(2) 0.0549(5) Uani 1 1 d . . . . .
C5 C 0.8275(5) 0.3583(2) 0.8771(3) 0.0788(8) Uani 1 1 d . . . . .
H5 H 0.936733 0.388122 0.850276 0.095 Uiso 1 1 calc R . . . .
C6 C 0.8657(7) 0.3306(3) 0.9855(4) 0.1035(13) Uani 1 1 d . . . . .
H6 H 0.998268 0.342825 1.031704 0.124 Uiso 1 1 calc R . . . .
C7 C 0.7062(7) 0.2849(3) 1.0250(4) 0.1008(12) Uani 1 1 d . . . . .
H7 H 0.730876 0.265757 1.097811 0.121 Uiso 1 1 calc R . . . .
C8 C 0.5116(7) 0.2679(3) 0.9563(4) 0.1021(13) Uani 1 1 d . . . . .
H8 H 0.404205 0.236782 0.982693 0.123 Uiso 1 1 calc R . . . .
C9 C 0.4729(5) 0.2962(2) 0.8486(3) 0.0775(8) Uani 1 1 d . . . . .
H9 H 0.339845 0.284106 0.802691 0.093 Uiso 1 1 calc R . . . .
C10 C -0.0057(5) 0.50954(16) 0.3788(2) 0.0612(6) Uani 1 1 d . . . . .
C11 C 0.0507(6) 0.5356(2) 0.2655(2) 0.0789(8) Uani 1 1 d . . . . .
H11A H 0.209557 0.530725 0.267819 0.095 Uiso 1 1 calc R . . . .
H11B H -0.021003 0.498576 0.208917 0.095 Uiso 1 1 calc R . . . .
C12 C -0.0182(6) 0.6209(2) 0.2322(2) 0.0795(8) Uani 1 1 d . . . . .
H12A H -0.178394 0.625658 0.222496 0.095 Uiso 1 1 calc R . . . .
H12B H 0.029085 0.634427 0.162151 0.095 Uiso 1 1 calc R . . . .
C13 C 0.0868(4) 0.67821(18) 0.3217(2) 0.0663(6) Uani 1 1 d . . . . .
H13A H 0.036874 0.732979 0.301754 0.080 Uiso 1 1 calc R . . . .
H13B H 0.246305 0.676920 0.324687 0.080 Uiso 1 1 calc R . . . .
C14 C 0.0343(3) 0.65870(13) 0.43776(18) 0.0506(4) Uani 1 1 d . . . . .
C15 C 0.1153(7) 0.42918(19) 0.4116(3) 0.0873(10) Uani 1 1 d . . . . .
H15A H 0.272498 0.438367 0.424394 0.131 Uiso 1 1 calc GR . . . .
H15B H 0.078365 0.390379 0.352673 0.131 Uiso 1 1 calc GR . . . .
H15C H 0.070687 0.408580 0.478309 0.131 Uiso 1 1 calc GR . . . .
C16 C -0.2554(6) 0.4959(3) 0.3720(3) 0.0883(9) Uani 1 1 d . . . . .
H16A H -0.289667 0.489225 0.445604 0.132 Uiso 1 1 calc GR . . . .
H16B H -0.298690 0.447988 0.328948 0.132 Uiso 1 1 calc GR . . . .
H16C H -0.334440 0.541968 0.337103 0.132 Uiso 1 1 calc GR . . . .
C17 C 0.1868(5) 0.71125(14) 0.5212(2) 0.0628(6) Uani 1 1 d . . . . .
H17A H 0.146483 0.705279 0.593723 0.094 Uiso 1 1 calc GR . . . .
H17B H 0.171934 0.767150 0.498778 0.094 Uiso 1 1 calc GR . . . .
H17C H 0.337748 0.694269 0.523493 0.094 Uiso 1 1 calc GR . . . .
C18 C -0.2063(4) 0.68145(18) 0.4456(2) 0.0673(6) Uani 1 1 d . . . . .
H18A H -0.301767 0.664562 0.379002 0.101 Uiso 1 1 calc GR . . . .
H18B H -0.217429 0.739214 0.454038 0.101 Uiso 1 1 calc GR . . . .
H18C H -0.250151 0.654779 0.508657 0.101 Uiso 1 1 calc GR . . . .
C19 C 0.1048(4) 0.56533(14) 0.76164(17) 0.0513(4) Uani 1 1 d . . . . .
H19 H -0.011291 0.526654 0.773119 0.062 Uiso 1 1 calc R . . . .
C20 C 0.2596(6) 0.5373(2) 0.9512(2) 0.0762(7) Uani 1 1 d . . . . .
C21 C 0.4711(9) 0.5255(3) 1.0280(3) 0.1128(15) Uani 1 1 d . . . . .
H21A H 0.560176 0.486280 0.997042 0.169 Uiso 1 1 calc GR . . . .
H21B H 0.441012 0.506302 1.098426 0.169 Uiso 1 1 calc GR . . . .
H21C H 0.549322 0.576197 1.038240 0.169 Uiso 1 1 calc GR . . . .
C22 C -0.1883(7) 0.6535(3) 0.7887(5) 0.1141(16) Uani 1 1 d . . . . .
H22A H -0.178140 0.644937 0.868111 0.137 Uiso 1 1 calc R . . . .
H22B H -0.288086 0.612873 0.750692 0.137 Uiso 1 1 calc R . . . .
C23 C -0.2784(6) 0.7346(3) 0.7599(4) 0.0948(11) Uani 1 1 d . . . . .
H23A H -0.288409 0.743215 0.681282 0.142 Uiso 1 1 calc GR . . . .
H23B H -0.182564 0.774823 0.799442 0.142 Uiso 1 1 calc GR . . . .
H23C H -0.423359 0.738957 0.780087 0.142 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.467(2) . ?
O1 C1 1.412(2) . ?
O2 C2 1.203(3) . ?
O3 C2 1.332(2) . ?
O3 C3 1.463(3) . ?
O4 C19 1.441(3) . ?
O4 C20 1.351(3) . ?
O5 C20 1.202(4) . ?
O6 C19 1.382(3) . ?
O6 C22 1.417(3) . ?
N1 C10 1.496(3) . ?
N1 C14 1.497(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.526(3) . ?
C1 C19 1.531(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.498(3) . ?
C4 C5 1.371(4) . ?
C4 C9 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.537(4) . ?
C10 C15 1.536(4) . ?
C10 C16 1.532(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.504(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.534(3) . ?
C14 C17 1.530(3) . ?
C14 C18 1.536(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9800 . ?
C20 C21 1.480(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.465(6) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N1 111.63(12) . . ?
C2 O3 C3 116.12(15) . . ?
C20 O4 C19 118.0(2) . . ?
C19 O6 C22 115.7(2) . . ?
O1 N1 C10 106.31(16) . . ?
O1 N1 C14 106.90(14) . . ?
C10 N1 C14 117.51(17) . . ?
O1 C1 H1 110.8 . . ?
O1 C1 C2 111.71(15) . . ?
O1 C1 C19 106.43(15) . . ?
C2 C1 H1 110.8 . . ?
C2 C1 C19 106.19(15) . . ?
C19 C1 H1 110.8 . . ?
O2 C2 O3 124.54(19) . . ?
O2 C2 C1 123.00(17) . . ?
O3 C2 C1 112.45(16) . . ?
O3 C3 H3A 109.0 . . ?
O3 C3 H3B 109.0 . . ?
O3 C3 C4 113.13(19) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 C9 118.7(3) . . ?
C9 C4 C3 121.6(2) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
N1 C10 C11 106.9(2) . . ?
N1 C10 C15 106.6(2) . . ?
N1 C10 C16 115.4(2) . . ?
C15 C10 C11 107.8(3) . . ?
C16 C10 C11 111.1(2) . . ?
C16 C10 C15 108.7(3) . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.2(2) . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C11 C12 C13 108.8(2) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C12 C13 C14 114.1(2) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
N1 C14 C13 107.52(19) . . ?
N1 C14 C17 107.97(16) . . ?
N1 C14 C18 115.21(19) . . ?
C13 C14 C18 110.65(19) . . ?
C17 C14 C13 107.3(2) . . ?
C17 C14 C18 107.9(2) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C1 103.20(16) . . ?
O4 C19 H19 110.5 . . ?
O6 C19 O4 110.70(18) . . ?
O6 C19 C1 111.31(17) . . ?
O6 C19 H19 110.5 . . ?
C1 C19 H19 110.5 . . ?
O4 C20 C21 111.4(3) . . ?
O5 C20 O4 122.4(3) . . ?
O5 C20 C21 126.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 H22A 109.4 . . ?
O6 C22 H22B 109.4 . . ?
O6 C22 C23 111.4(3) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C10 C11 173.85(19) . . . . ?
O1 N1 C10 C15 -71.1(3) . . . . ?
O1 N1 C10 C16 49.8(3) . . . . ?
O1 N1 C14 C13 -173.28(16) . . . . ?
O1 N1 C14 C17 71.2(2) . . . . ?
O1 N1 C14 C18 -49.4(2) . . . . ?
O1 C1 C2 O2 -50.6(3) . . . . ?
O1 C1 C2 O3 130.11(17) . . . . ?
O1 C1 C19 O4 179.59(16) . . . . ?
O1 C1 C19 O6 -61.6(2) . . . . ?
O3 C3 C4 C5 -90.0(3) . . . . ?
O3 C3 C4 C9 93.5(3) . . . . ?
N1 O1 C1 C2 -92.00(17) . . . . ?
N1 O1 C1 C19 152.52(15) . . . . ?
N1 C10 C11 C12 -54.3(3) . . . . ?
C1 O1 N1 C10 127.38(17) . . . . ?
C1 O1 N1 C14 -106.33(16) . . . . ?
C2 O3 C3 C4 -81.3(2) . . . . ?
C2 C1 C19 O4 60.44(19) . . . . ?
C2 C1 C19 O6 179.21(16) . . . . ?
C3 O3 C2 O2 0.8(3) . . . . ?
C3 O3 C2 C1 -179.98(17) . . . . ?
C3 C4 C5 C6 -178.3(4) . . . . ?
C3 C4 C9 C8 177.6(3) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
C5 C4 C9 C8 1.0(5) . . . . ?
C5 C6 C7 C8 -0.4(8) . . . . ?
C6 C7 C8 C9 -0.3(8) . . . . ?
C7 C8 C9 C4 0.0(7) . . . . ?
C9 C4 C5 C6 -1.7(6) . . . . ?
C10 N1 C14 C13 -54.0(2) . . . . ?
C10 N1 C14 C17 -169.5(2) . . . . ?
C10 N1 C14 C18 69.9(3) . . . . ?
C10 C11 C12 C13 56.6(4) . . . . ?
C11 C12 C13 C14 -55.9(3) . . . . ?
C12 C13 C14 N1 53.4(3) . . . . ?
C12 C13 C14 C17 169.3(2) . . . . ?
C12 C13 C14 C18 -73.2(3) . . . . ?
C14 N1 C10 C11 54.3(3) . . . . ?
C14 N1 C10 C15 169.3(2) . . . . ?
C14 N1 C10 C16 -69.8(3) . . . . ?
C15 C10 C11 C12 -168.6(3) . . . . ?
C16 C10 C11 C12 72.3(4) . . . . ?
C19 O4 C20 O5 -4.0(5) . . . . ?
C19 O4 C20 C21 176.2(3) . . . . ?
C19 O6 C22 C23 -167.8(3) . . . . ?
C19 C1 C2 O2 65.0(2) . . . . ?
C19 C1 C2 O3 -114.26(18) . . . . ?
C20 O4 C19 O6 88.1(3) . . . . ?
C20 O4 C19 C1 -152.7(2) . . . . ?
C22 O6 C19 O4 -113.3(3) . . . . ?
C22 O6 C19 C1 132.5(3) . . . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.880
_oxdiff_exptl_absorpt_empirical_full_min 0.772
