# Electronic Supplementary Material (ESI) for ChemComm.
# 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_s5292r
_database_code_depnum_ccdc_archive 'CCDC 1976239'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica-yrezabal '
;Univeristy of Manchester
United Kingdom
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_audit_creation_date             2018-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H18 N2 O4)'
_chemical_formula_sum            'C34 H36 N4 O8'
_chemical_formula_weight         628.67
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     grh
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.8960(5)
_cell_length_b                   15.0948(3)
_cell_length_c                   22.5368(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.389(3)
_cell_angle_gamma                90
_cell_volume                     6253.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8714
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4180
_cell_measurement_theta_min      1.7410
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2656
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.775
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.640
_diffrn_reflns_theta_min         1.746
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.775
_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  56.00   1.00   20.00    --   -7.80  63.00 102.00   76
  2  ω    -86.00  26.00   1.00   20.00    --   -7.80 -63.00 -33.00  112
  3  ω    -82.00   2.00   1.00   20.00    --    5.00 -57.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0098926000
_diffrn_orient_matrix_UB_12      -0.0285258000
_diffrn_orient_matrix_UB_13      -0.0255915000
_diffrn_orient_matrix_UB_21      -0.0270777000
_diffrn_orient_matrix_UB_22      -0.0196244000
_diffrn_orient_matrix_UB_23      0.0128993000
_diffrn_orient_matrix_UB_31      -0.0256385000
_diffrn_orient_matrix_UB_32      0.0317684000
_diffrn_orient_matrix_UB_33      -0.0150211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5860
_reflns_number_total             7484
_reflns_odcompleteness_completeness 99.79
_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 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14d (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         0.445
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.052
_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)+(0.0474P)²+9.0095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1370
_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, All N(H) groups
2.a Riding coordinates:
 N13(H13), N36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C46(H46), C22(H22), C23(H23), C3(H3), C5(H5), C21(H21),
 C20(H20), C6(H6), C25(H25), C42(H42), C29(H29), C45(H45), C28(H28), C26(H26),
 C44(H44), C43(H43)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C37(H37A,H37B,H37C), C11(H11A,H11B,H11C), C34(H34A,H34B,
 H34C)
;
_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
O9 O 0.37885(7) 0.93087(8) 0.47287(6) 0.0277(3) Uani 1 1 d . . . . .
O12 O 0.26796(7) 0.89375(9) 0.41810(7) 0.0335(3) Uani 1 1 d . . . . .
O32 O 0.46305(8) 0.22044(9) 0.37834(6) 0.0357(3) Uani 1 1 d . . . . .
O35 O 0.41674(8) 0.26152(9) 0.28139(6) 0.0355(3) Uani 1 1 d . . . . .
N13 N 0.39944(8) 0.75337(9) 0.50099(6) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.4365 0.7917 0.5128 0.033 Uiso 1 1 d R . . . .
N36 N 0.51418(8) 0.39938(10) 0.38771(7) 0.0253(3) Uani 1 1 d . . . . .
H36 H 0.5329 0.3626 0.4209 0.038 Uiso 1 1 d R . . . .
O17 O 0.17334(9) 0.43978(10) 0.33698(8) 0.0520(4) Uani 1 1 d . . . . .
O16 O 0.14195(9) 0.52484(10) 0.25864(7) 0.0499(4) Uani 1 1 d . . . . .
N15 N 0.17572(9) 0.51009(11) 0.31123(8) 0.0332(4) Uani 1 1 d . . . . .
N38 N 0.29290(11) 0.64213(13) 0.19581(9) 0.0429(4) Uani 1 1 d . . . . .
O40 O 0.31431(10) 0.71870(12) 0.20419(10) 0.0715(6) Uani 1 1 d . . . . .
C18 C 0.42526(9) 0.79096(11) 0.40184(8) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.31716(9) 0.62576(11) 0.42757(8) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.3514 0.6121 0.4632 0.027 Uiso 1 1 calc R . . . .
C8 C 0.33011(9) 0.87435(11) 0.44034(8) 0.0224(3) Uani 1 1 d . . . . .
C19 C 0.41800(10) 0.85158(11) 0.35417(8) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.3781 0.8894 0.3455 0.030 Uiso 1 1 calc R . . . .
C46 C 0.41961(10) 0.42480(12) 0.46520(8) 0.0267(4) Uani 1 1 d . . . . .
H46 H 0.4608 0.4600 0.4689 0.032 Uiso 1 1 calc R . . . .
C1 C 0.31185(9) 0.71243(11) 0.40557(8) 0.0201(3) Uani 1 1 d . . . . .
C41 C 0.39694(9) 0.37180(11) 0.41401(8) 0.0232(4) Uani 1 1 d . . . . .
C24 C 0.40016(10) 0.44302(11) 0.31591(8) 0.0235(4) Uani 1 1 d . . . . .
C22 C 0.53661(10) 0.73926(12) 0.37894(8) 0.0278(4) Uani 1 1 d . . . . .
H22 H 0.5765 0.7014 0.3873 0.033 Uiso 1 1 calc R . . . .
C7 C 0.36642(9) 0.78245(11) 0.43835(8) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.22264(9) 0.58078(11) 0.34392(8) 0.0246(4) Uani 1 1 d . . . . .
C23 C 0.48481(10) 0.73429(12) 0.41374(8) 0.0251(4) Uani 1 1 d . . . . .
H23 H 0.4900 0.6929 0.4450 0.030 Uiso 1 1 calc R . . . .
C3 C 0.27221(9) 0.55966(11) 0.39707(8) 0.0242(4) Uani 1 1 d . . . . .
H3 H 0.2755 0.5021 0.4122 0.029 Uiso 1 1 calc R . . . .
C31 C 0.43615(10) 0.27991(12) 0.33456(8) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.35007(10) 0.75898(13) 0.54222(8) 0.0274(4) Uani 1 1 d . . . . .
H14A H 0.3123 0.7154 0.5308 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.3288 0.8170 0.5396 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.3767 0.7482 0.5833 0.041 Uiso 1 1 calc GR . . . .
C5 C 0.21630(10) 0.66559(12) 0.32014(9) 0.0272(4) Uani 1 1 d . . . . .
H5 H 0.1825 0.6784 0.2841 0.033 Uiso 1 1 calc R . . . .
C30 C 0.43786(9) 0.37360(11) 0.36272(8) 0.0226(3) Uani 1 1 d . . . . .
C21 C 0.52936(10) 0.80009(12) 0.33193(9) 0.0284(4) Uani 1 1 d . . . . .
H21 H 0.5642 0.8034 0.3089 0.034 Uiso 1 1 calc R . . . .
O39 O 0.23960(13) 0.62095(13) 0.15634(9) 0.0812(7) Uani 1 1 d . . . . .
C20 C 0.46970(10) 0.85594(12) 0.31968(8) 0.0282(4) Uani 1 1 d . . . . .
H20 H 0.4643 0.8967 0.2880 0.034 Uiso 1 1 calc R . . . .
C6 C 0.26132(10) 0.73101(12) 0.35122(8) 0.0254(4) Uani 1 1 d . . . . .
H6 H 0.2579 0.7883 0.3357 0.030 Uiso 1 1 calc R . . . .
C25 C 0.33728(10) 0.42349(12) 0.27143(9) 0.0293(4) Uani 1 1 d . . . . .
H25 H 0.3183 0.3664 0.2686 0.035 Uiso 1 1 calc R . . . .
C42 C 0.33416(11) 0.32113(12) 0.40877(9) 0.0308(4) Uani 1 1 d . . . . .
H42 H 0.3178 0.2860 0.3745 0.037 Uiso 1 1 calc R . . . .
C29 C 0.42569(10) 0.53005(12) 0.32103(9) 0.0289(4) Uani 1 1 d . . . . .
H29 H 0.4667 0.5442 0.3512 0.035 Uiso 1 1 calc R . . . .
C45 C 0.38150(11) 0.42586(13) 0.51104(9) 0.0329(4) Uani 1 1 d . . . . .
H45 H 0.3975 0.4612 0.5453 0.039 Uiso 1 1 calc R . . . .
C28 C 0.39109(11) 0.59585(13) 0.28210(9) 0.0321(4) Uani 1 1 d . . . . .
H28 H 0.4083 0.6538 0.2859 0.039 Uiso 1 1 calc R . . . .
C26 C 0.30292(11) 0.48820(13) 0.23150(9) 0.0320(4) Uani 1 1 d . . . . .
H26 H 0.2620 0.4746 0.2011 0.038 Uiso 1 1 calc R . . . .
C27 C 0.33037(11) 0.57311(13) 0.23748(9) 0.0312(4) Uani 1 1 d . . . . .
C44 C 0.31957(12) 0.37436(14) 0.50569(9) 0.0353(5) Uani 1 1 d . . . . .
H44 H 0.2941 0.3745 0.5364 0.042 Uiso 1 1 calc R . . . .
C37 C 0.56110(11) 0.39534(14) 0.34411(9) 0.0340(4) Uani 1 1 d . . . . .
H37A H 0.5454 0.4387 0.3127 0.051 Uiso 1 1 calc GR . . . .
H37B H 0.5581 0.3374 0.3262 0.051 Uiso 1 1 calc GR . . . .
H37C H 0.6105 0.4073 0.3650 0.051 Uiso 1 1 calc GR . . . .
C10 C 0.35115(12) 1.01951(12) 0.48008(10) 0.0368(5) Uani 1 1 d . . . . .
H10A H 0.3094 1.0160 0.4982 0.044 Uiso 1 1 calc R . . . .
H10B H 0.3361 1.0482 0.4407 0.044 Uiso 1 1 calc R . . . .
C43 C 0.29603(11) 0.32282(14) 0.45426(10) 0.0372(5) Uani 1 1 d . . . . .
H43 H 0.2541 0.2889 0.4502 0.045 Uiso 1 1 calc R . . . .
C33 C 0.46196(12) 0.12765(13) 0.35920(11) 0.0396(5) Uani 1 1 d . . . . .
H33A H 0.4197 0.1173 0.3262 0.047 Uiso 1 1 calc R . . . .
H33B H 0.4581 0.0896 0.3930 0.047 Uiso 1 1 calc R . . . .
C11 C 0.41078(15) 1.07131(16) 0.52050(12) 0.0537(6) Uani 1 1 d . . . . .
H11A H 0.4534 1.0696 0.5042 0.081 Uiso 1 1 calc GR . . . .
H11B H 0.4217 1.0460 0.5607 0.081 Uiso 1 1 calc GR . . . .
H11C H 0.3955 1.1316 0.5226 0.081 Uiso 1 1 calc GR . . . .
C34 C 0.52854(14) 0.10504(15) 0.33870(12) 0.0508(6) Uani 1 1 d . . . . .
H34A H 0.5334 0.1442 0.3063 0.076 Uiso 1 1 calc GR . . . .
H34B H 0.5254 0.0450 0.3243 0.076 Uiso 1 1 calc GR . . . .
H34C H 0.5701 0.1112 0.3722 0.076 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
O9 C8 1.342(2) . ?
O9 C10 1.459(2) . ?
O12 C8 1.201(2) . ?
O32 C31 1.344(2) . ?
O32 C33 1.464(2) . ?
O35 C31 1.202(2) . ?
N13 H13 0.8994 . ?
N13 C7 1.472(2) . ?
N13 C14 1.464(2) . ?
N36 H36 0.9329 . ?
N36 C30 1.474(2) . ?
N36 C37 1.469(2) . ?
O17 N15 1.215(2) . ?
O16 N15 1.229(2) . ?
N15 C4 1.471(2) . ?
N38 O40 1.225(3) . ?
N38 O39 1.222(3) . ?
N38 C27 1.470(3) . ?
C18 C19 1.394(2) . ?
C18 C7 1.534(2) . ?
C18 C23 1.389(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.394(2) . ?
C2 C3 1.385(2) . ?
C8 C7 1.553(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(3) . ?
C46 H46 0.9300 . ?
C46 C41 1.388(2) . ?
C46 C45 1.389(3) . ?
C1 C7 1.541(2) . ?
C1 C6 1.396(2) . ?
C41 C30 1.532(2) . ?
C41 C42 1.393(3) . ?
C24 C30 1.540(2) . ?
C24 C25 1.397(3) . ?
C24 C29 1.395(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(2) . ?
C22 C21 1.385(3) . ?
C4 C3 1.376(3) . ?
C4 C5 1.382(2) . ?
C23 H23 0.9300 . ?
C3 H3 0.9300 . ?
C31 C30 1.547(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C6 H6 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.384(3) . ?
C42 H42 0.9300 . ?
C42 C43 1.383(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.385(3) . ?
C45 H45 0.9300 . ?
C45 C44 1.387(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.378(3) . ?
C44 H44 0.9300 . ?
C44 C43 1.381(3) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.495(3) . ?
C43 H43 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.477(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 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
C8 O9 C10 115.15(14) . . ?
C31 O32 C33 116.46(15) . . ?
C7 N13 H13 102.7 . . ?
C14 N13 H13 109.9 . . ?
C14 N13 C7 113.62(13) . . ?
C30 N36 H36 107.8 . . ?
C37 N36 H36 109.6 . . ?
C37 N36 C30 114.97(15) . . ?
O17 N15 O16 123.37(17) . . ?
O17 N15 C4 118.61(16) . . ?
O16 N15 C4 118.00(16) . . ?
O40 N38 C27 118.51(19) . . ?
O39 N38 O40 123.12(19) . . ?
O39 N38 C27 118.27(19) . . ?
C19 C18 C7 120.95(15) . . ?
C23 C18 C19 118.93(16) . . ?
C23 C18 C7 120.01(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C3 C2 C1 120.93(16) . . ?
O9 C8 C7 109.37(14) . . ?
O12 C8 O9 123.63(16) . . ?
O12 C8 C7 126.97(16) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.54(16) . . ?
C20 C19 H19 119.7 . . ?
C41 C46 H46 119.6 . . ?
C41 C46 C45 120.76(18) . . ?
C45 C46 H46 119.6 . . ?
C2 C1 C7 119.22(15) . . ?
C2 C1 C6 118.60(16) . . ?
C6 C1 C7 121.92(15) . . ?
C46 C41 C30 120.29(15) . . ?
C46 C41 C42 118.66(17) . . ?
C42 C41 C30 120.95(16) . . ?
C25 C24 C30 121.98(16) . . ?
C29 C24 C30 119.21(15) . . ?
C29 C24 C25 118.58(16) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.62(17) . . ?
N13 C7 C18 109.91(13) . . ?
N13 C7 C8 109.31(13) . . ?
N13 C7 C1 110.07(13) . . ?
C18 C7 C8 108.70(13) . . ?
C18 C7 C1 106.74(13) . . ?
C1 C7 C8 112.06(13) . . ?
C3 C4 N15 118.53(16) . . ?
C3 C4 C5 122.16(16) . . ?
C5 C4 N15 119.30(16) . . ?
C18 C23 C22 120.15(16) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.72(16) . . ?
C4 C3 H3 120.6 . . ?
O32 C31 C30 109.94(15) . . ?
O35 C31 O32 123.66(17) . . ?
O35 C31 C30 126.34(17) . . ?
N13 C14 H14A 109.5 . . ?
N13 C14 H14B 109.5 . . ?
N13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.49(17) . . ?
C6 C5 H5 120.8 . . ?
N36 C30 C41 109.67(14) . . ?
N36 C30 C24 109.79(14) . . ?
N36 C30 C31 108.88(14) . . ?
C41 C30 C24 107.14(14) . . ?
C41 C30 C31 109.08(14) . . ?
C24 C30 C31 112.24(14) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 C22 119.25(16) . . ?
C20 C21 H21 120.4 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.50(17) . . ?
C21 C20 H20 119.8 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.08(16) . . ?
C5 C6 H6 119.5 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.71(18) . . ?
C26 C25 H25 119.6 . . ?
C41 C42 H42 119.8 . . ?
C43 C42 C41 120.44(18) . . ?
C43 C42 H42 119.8 . . ?
C24 C29 H29 119.3 . . ?
C28 C29 C24 121.30(17) . . ?
C28 C29 H29 119.3 . . ?
C46 C45 H45 120.0 . . ?
C44 C45 C46 120.07(19) . . ?
C44 C45 H45 120.0 . . ?
C29 C28 H28 120.9 . . ?
C27 C28 C29 118.24(18) . . ?
C27 C28 H28 120.9 . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 118.93(18) . . ?
C27 C26 H26 120.5 . . ?
C28 C27 N38 118.98(18) . . ?
C26 C27 N38 118.83(18) . . ?
C26 C27 C28 122.18(18) . . ?
C45 C44 H44 120.3 . . ?
C43 C44 C45 119.34(19) . . ?
C43 C44 H44 120.3 . . ?
N36 C37 H37A 109.5 . . ?
N36 C37 H37B 109.5 . . ?
N36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O9 C10 H10A 110.1 . . ?
O9 C10 H10B 110.1 . . ?
O9 C10 C11 107.94(17) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C42 C43 H43 119.6 . . ?
C44 C43 C42 120.71(19) . . ?
C44 C43 H43 119.6 . . ?
O32 C33 H33A 109.4 . . ?
O32 C33 H33B 109.4 . . ?
O32 C33 C34 110.99(18) . . ?
H33A C33 H33B 108.0 . . ?
C34 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
O9 C8 C7 N13 53.56(17) . . . . ?
O9 C8 C7 C18 -66.41(17) . . . . ?
O9 C8 C7 C1 175.86(13) . . . . ?
O12 C8 C7 N13 -124.78(19) . . . . ?
O12 C8 C7 C18 115.24(19) . . . . ?
O12 C8 C7 C1 -2.5(2) . . . . ?
O32 C31 C30 N36 64.36(19) . . . . ?
O32 C31 C30 C41 -55.29(19) . . . . ?
O32 C31 C30 C24 -173.87(15) . . . . ?
O35 C31 C30 N36 -112.8(2) . . . . ?
O35 C31 C30 C41 127.5(2) . . . . ?
O35 C31 C30 C24 8.9(3) . . . . ?
O17 N15 C4 C3 12.3(3) . . . . ?
O17 N15 C4 C5 -168.42(18) . . . . ?
O16 N15 C4 C3 -166.26(18) . . . . ?
O16 N15 C4 C5 13.0(3) . . . . ?
N15 C4 C3 C2 179.15(16) . . . . ?
N15 C4 C5 C6 -179.43(16) . . . . ?
O40 N38 C27 C28 -4.1(3) . . . . ?
O40 N38 C27 C26 174.7(2) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C2 C1 C7 N13 -20.5(2) . . . . ?
C2 C1 C7 C18 98.75(17) . . . . ?
C2 C1 C7 C8 -142.36(15) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C8 O9 C10 C11 176.38(18) . . . . ?
C19 C18 C7 N13 -150.85(15) . . . . ?
C19 C18 C7 C8 -31.2(2) . . . . ?
C19 C18 C7 C1 89.80(18) . . . . ?
C19 C18 C23 C22 0.9(3) . . . . ?
C46 C41 C30 N36 26.8(2) . . . . ?
C46 C41 C30 C24 -92.33(18) . . . . ?
C46 C41 C30 C31 145.95(16) . . . . ?
C46 C41 C42 C43 -1.0(3) . . . . ?
C46 C45 C44 C43 -0.5(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C41 C46 C45 C44 -0.7(3) . . . . ?
C41 C42 C43 C44 -0.2(3) . . . . ?
C24 C25 C26 C27 -2.0(3) . . . . ?
C24 C29 C28 C27 -0.3(3) . . . . ?
C22 C21 C20 C19 0.4(3) . . . . ?
C7 C18 C19 C20 -177.00(16) . . . . ?
C7 C18 C23 C22 177.19(16) . . . . ?
C7 C1 C6 C5 175.29(16) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C23 C18 C19 C20 -0.7(3) . . . . ?
C23 C18 C7 N13 32.9(2) . . . . ?
C23 C18 C7 C8 152.52(16) . . . . ?
C23 C18 C7 C1 -86.43(18) . . . . ?
C23 C22 C21 C20 -0.2(3) . . . . ?
C3 C2 C1 C7 -175.74(15) . . . . ?
C3 C2 C1 C6 -1.5(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C31 O32 C33 C34 87.9(2) . . . . ?
C14 N13 C7 C18 169.43(14) . . . . ?
C14 N13 C7 C8 50.20(18) . . . . ?
C14 N13 C7 C1 -73.28(17) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C30 C41 C42 C43 -177.37(17) . . . . ?
C30 C24 C25 C26 177.39(17) . . . . ?
C30 C24 C29 C28 -176.37(17) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
O39 N38 C27 C28 179.5(2) . . . . ?
O39 N38 C27 C26 -1.7(3) . . . . ?
C6 C1 C7 N13 165.47(15) . . . . ?
C6 C1 C7 C18 -75.29(19) . . . . ?
C6 C1 C7 C8 43.6(2) . . . . ?
C25 C24 C30 N36 158.95(16) . . . . ?
C25 C24 C30 C41 -82.01(19) . . . . ?
C25 C24 C30 C31 37.7(2) . . . . ?
C25 C24 C29 C28 -1.7(3) . . . . ?
C25 C26 C27 N38 -178.77(18) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C42 C41 C30 N36 -156.89(16) . . . . ?
C42 C41 C30 C24 84.00(19) . . . . ?
C42 C41 C30 C31 -37.7(2) . . . . ?
C29 C24 C30 N36 -26.6(2) . . . . ?
C29 C24 C30 C41 92.45(19) . . . . ?
C29 C24 C30 C31 -147.83(16) . . . . ?
C29 C24 C25 C26 2.9(3) . . . . ?
C29 C28 C27 N38 179.92(18) . . . . ?
C29 C28 C27 C26 1.2(3) . . . . ?
C45 C46 C41 C30 177.87(16) . . . . ?
C45 C46 C41 C42 1.5(3) . . . . ?
C45 C44 C43 C42 1.0(3) . . . . ?
C37 N36 C30 C41 174.41(15) . . . . ?
C37 N36 C30 C24 -68.12(19) . . . . ?
C37 N36 C30 C31 55.13(19) . . . . ?
C10 O9 C8 O12 0.3(3) . . . . ?
C10 O9 C8 C7 -178.14(15) . . . . ?
C33 O32 C31 O35 -5.4(3) . . . . ?
C33 O32 C31 C30 177.27(16) . . . . ?

_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 2.258
_oxdiff_exptl_absorpt_empirical_full_min 0.569
