# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_s6380a
_database_code_depnum_ccdc_archive 'CCDC 2342281'
loop_
_audit_author_name
_audit_author_address
'Avantika Hasija'
;the University of Manchester
United Kingdom
;
_audit_update_record             
;
2024-03-21 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_chemical_melting_point          ?
# start Validation Reply Form
_vrf_PLAT910_s6380a              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         15 Note  
RESPONSE: The alert is due to missing reflections at low resolution effected 
by the beam stop. As the completeness of data is as per criteria, there is no 
requirement for collecting additional data with detector at larger distance.
;
# end Validation Reply Form
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      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                   8.1324(3)
_cell_length_b                   11.0134(5)
_cell_length_c                   20.2400(8)
_cell_angle_alpha                77.534(4)
_cell_angle_beta                 79.396(4)
_cell_angle_gamma                80.934(4)
_cell_volume                     1726.67(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17862
_cell_measurement_temperature    99.7(7)
_cell_measurement_theta_max      31.2790
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 27 0.0766
2 -6 -26 0.0666
11 5 14 0.0588
-11 -1 1 0.0860
7 -11 -3 0.0685
-5 -7 18 0.0836
0 12 -13 0.0453
-4 13 -3 0.0603
1 -12 14 0.0462
1 -14 3 0.0661
6 -11 -8 0.0638
0 -6 23 0.0500
2 14 17 0.0597

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            60067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.588
_diffrn_reflns_theta_min         3.338
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.7(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00 101.00   1.00    7.50    --   26.88  19.00   0.00  124
  2  ω      5.00  96.00   1.00    7.50    --   26.88  57.00  30.00   91
  3  ω    -15.00  69.00   1.00    7.50    --   26.88 -99.00-120.00   84
  4  ω    -46.00  54.00   1.00    7.50    --   26.88 -37.00 150.00  100
  5  ω    -15.00  69.00   1.00    7.50    --   26.88 -99.00 120.00   84
  6  ω     -5.00  42.00   1.00    7.50    --   26.88  77.00   0.00   47
  7  ω     37.00 105.00   1.00    7.50    --   26.88-178.00 150.00   68
  8  ω     -5.00  42.00   1.00    7.50    --   26.88  77.00 120.00   47
  9  ω     39.00 105.00   1.00    7.50    --   26.88 178.00  60.00   66
 10  ω     -5.00  42.00   1.00    7.50    --   26.88  77.00 -90.00   47
 11  ω    -46.00  54.00   1.00    7.50    --   26.88 -37.00-120.00  100
 12  ω    -42.00  48.00   1.00    7.50    --   26.88 -57.00  30.00   90
 13  ω      5.00  96.00   1.00    7.50    --   26.88  57.00-180.00   91
 14  ω    -98.00   2.00   1.00    7.50    --  -25.16 -37.00-150.00  100
 15  ω    -42.00   6.00   1.00    7.50    --  -25.16 -77.00-180.00   48
 16  ω    -15.00  69.00   1.00    7.50    --   26.88 -99.00 -30.00   84
 17  ω     37.00 105.00   1.00    7.50    --   26.88-178.00  90.00   68
 18  ω      5.00  96.00   1.00    7.50    --   26.88  57.00 120.00   91
 19  ω     -5.00  42.00   1.00    7.50    --   26.88  77.00 150.00   47
 20  ω    -94.00 -67.00   1.00    7.50    --  -25.16 -57.00  30.00   27
 21  φ     30.00 300.00   1.00    0.50   0.00   0.00   0.00    --   270
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147264000
_diffrn_orient_matrix_UB_12      0.0628776000
_diffrn_orient_matrix_UB_13      -0.0177112000
_diffrn_orient_matrix_UB_21      0.0453000000
_diffrn_orient_matrix_UB_22      0.0198233000
_diffrn_orient_matrix_UB_23      0.0218202000
_diffrn_orient_matrix_UB_31      0.0758943000
_diffrn_orient_matrix_UB_32      -0.0092743000
_diffrn_orient_matrix_UB_33      -0.0231518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                8296
_reflns_number_total             10899
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         10899
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.031
_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)+(0.0370P)²+1.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1232
_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 C(H,H,H,H,H,H) groups
2. Restrained distances
 O3-C18 \\sim O3-C01F
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C18 \\sim C01F: within 2A with sigma of 0.006 and sigma for terminal
atoms of 0.012 within 2A
4. Rigid body (RIGU) restrains
 C01F, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C01F)=Sof(H01A)=Sof(H01B)=1-FVAR(1)
 Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C37(H37A,H37B), C9(H9A,H9B), C18(H18A,H18B), C01F(H01A,H01B)
6.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C6(H6), C24(H24), C5(H5), C13(H13), C3(H3), C2(H2A), C15(H15),
 C31(H31), C21(H21), C12(H12), C25(H25), C11(H11), C16(H16), C35(H35), C34(H34),
  C33(H33), C32(H32)
6.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C10(H10A,H10B,H10C), C29(H29A,H29B,H29C), C19(H19A,H19B,
 H19C), C19(H19D,H19E,H19F)
;
_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
O4 O 0.12313(12) 0.12309(9) 0.48835(5) 0.01688(19) Uani 1 1 d . . . . .
O8 O 0.10272(12) 0.61721(9) 0.00652(5) 0.01634(19) Uani 1 1 d . . . . .
O7 O 0.25709(12) 0.76584(9) 0.01504(5) 0.01666(19) Uani 1 1 d . . . . .
O3 O 0.28593(12) 0.27619(10) 0.48047(5) 0.0205(2) Uani 1 1 d D . . . .
O6 O 0.95142(12) 0.74624(10) 0.15749(6) 0.0238(2) Uani 1 1 d . . . . .
O5 O 0.76851(13) 0.78078(11) 0.24599(6) 0.0264(2) Uani 1 1 d . . . . .
O1 O 1.09612(13) 0.34628(11) 0.33041(6) 0.0282(2) Uani 1 1 d . . . . .
O2 O 0.94462(14) 0.49028(10) 0.26870(6) 0.0265(2) Uani 1 1 d . . . . .
N4 N 0.15507(14) 0.39287(11) 0.09202(6) 0.0150(2) Uani 1 1 d . . . . .
N2 N 0.25119(15) -0.05470(11) 0.41560(6) 0.0161(2) Uani 1 1 d . . . . .
N3 N 0.80807(14) 0.74730(11) 0.19025(6) 0.0176(2) Uani 1 1 d . . . . .
N1 N 0.96114(15) 0.39233(11) 0.31073(6) 0.0188(2) Uani 1 1 d . . . . .
C36 C 0.21138(16) 0.64857(12) 0.03256(6) 0.0133(2) Uani 1 1 d . . . . .
C23 C 0.43130(16) 0.62445(12) 0.10962(6) 0.0129(2) Uani 1 1 d . . . . .
C4 C 0.53894(16) 0.19337(12) 0.39018(6) 0.0133(2) Uani 1 1 d . . . . .
C27 C 0.26830(15) 0.44933(12) 0.11309(6) 0.0132(2) Uani 1 1 d . . . . .
C20 C 0.67646(16) 0.70772(12) 0.16152(7) 0.0148(2) Uani 1 1 d . . . . .
C17 C 0.25447(16) 0.16987(12) 0.46408(7) 0.0141(2) Uani 1 1 d . . . . .
C1 C 0.81334(16) 0.32507(13) 0.33898(7) 0.0152(2) Uani 1 1 d . . . . .
C7 C 0.39190(16) 0.12081(12) 0.41684(6) 0.0134(2) Uani 1 1 d . . . . .
C30 C 0.11378(17) 0.26941(13) 0.12272(7) 0.0155(2) Uani 1 1 d . . . . .
C22 C 0.39048(17) 0.67299(13) 0.16988(7) 0.0172(3) Uani 1 1 d . . . . .
H22 H 0.277394 0.678007 0.192842 0.021 Uiso 1 1 calc R U . . .
C26 C 0.30252(15) 0.57015(12) 0.08448(6) 0.0130(2) Uani 1 1 d . . . . .
C14 C 0.23984(16) -0.16809(12) 0.39415(7) 0.0145(2) Uani 1 1 d . . . . .
C6 C 0.66038(17) 0.37322(13) 0.31649(7) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.649532 0.449739 0.284335 0.021 Uiso 1 1 calc R U . . .
C24 C 0.59675(17) 0.62318(13) 0.07472(7) 0.0171(3) Uani 1 1 d . . . . .
H24 H 0.624719 0.593461 0.032847 0.021 Uiso 1 1 calc R U . . .
C5 C 0.52358(16) 0.30606(13) 0.34244(7) 0.0161(2) Uani 1 1 d . . . . .
H5 H 0.418018 0.337065 0.327568 0.019 Uiso 1 1 calc R U . . .
C13 C 0.13283(17) -0.16674(14) 0.34753(7) 0.0181(3) Uani 1 1 d . . . . .
H13 H 0.066248 -0.091240 0.330874 0.022 Uiso 1 1 calc R U . . .
C8 C 0.38431(16) 0.01196(12) 0.39440(6) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.69475(17) 0.15007(13) 0.41201(7) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.706113 0.074515 0.444857 0.022 Uiso 1 1 calc R U . . .
C2 C 0.83336(17) 0.21510(14) 0.38673(7) 0.0193(3) Uani 1 1 d . . . . .
H2A H 0.938915 0.184979 0.401775 0.023 Uiso 1 1 calc R U . . .
C28 C 0.36243(16) 0.37245(13) 0.16885(7) 0.0160(2) Uani 1 1 d . . . . .
H28A H 0.293892 0.307299 0.196787 0.019 Uiso 1 1 calc R U . . .
H28B H 0.379427 0.427305 0.199225 0.019 Uiso 1 1 calc R U . . .
C15 C 0.33459(18) -0.27912(13) 0.41982(7) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.404430 -0.280608 0.452872 0.022 Uiso 1 1 calc R U . . .
C31 C -0.02422(18) 0.25447(14) 0.17476(7) 0.0194(3) Uani 1 1 d . . . . .
H31 H -0.091002 0.325809 0.189098 0.023 Uiso 1 1 calc R U . . .
C21 C 0.51301(17) 0.71400(13) 0.19668(7) 0.0176(3) Uani 1 1 d . . . . .
H21 H 0.485334 0.745496 0.238021 0.021 Uiso 1 1 calc R U . . .
C12 C 0.12382(18) -0.27634(14) 0.32545(7) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.050539 -0.275838 0.293829 0.024 Uiso 1 1 calc R U . . .
C37 C 0.16304(18) 0.85507(13) -0.03235(7) 0.0189(3) Uani 1 1 d . . . . .
H37A H 0.046813 0.877230 -0.009642 0.023 Uiso 1 1 calc R U . . .
H37B H 0.156910 0.818666 -0.072355 0.023 Uiso 1 1 calc R U . . .
C25 C 0.72117(17) 0.66470(13) 0.10025(7) 0.0181(3) Uani 1 1 d . . . . .
H25 H 0.833380 0.663606 0.076429 0.022 Uiso 1 1 calc R U . . .
C9 C 0.51916(17) -0.03081(13) 0.33903(7) 0.0174(3) Uani 1 1 d . . . . .
H9A H 0.534899 -0.123454 0.346324 0.021 Uiso 1 1 calc R U . . .
H9B H 0.627480 -0.002813 0.341331 0.021 Uiso 1 1 calc R U . . .
C11 C 0.22174(18) -0.38637(14) 0.34955(7) 0.0202(3) Uani 1 1 d . . . . .
H11 H 0.217138 -0.460734 0.333709 0.024 Uiso 1 1 calc R U . . .
C16 C 0.32649(19) -0.38799(14) 0.39681(7) 0.0208(3) Uani 1 1 d . . . . .
H16 H 0.392798 -0.463628 0.413469 0.025 Uiso 1 1 calc R U . . .
C38 C 0.2537(2) 0.97003(14) -0.05506(8) 0.0236(3) Uani 1 1 d . . . . .
H38A H 0.190157 1.033891 -0.085646 0.035 Uiso 1 1 calc R U . . .
H38B H 0.366621 0.947766 -0.079411 0.035 Uiso 1 1 calc R U . . .
H38C H 0.263358 1.003109 -0.014885 0.035 Uiso 1 1 calc R U . . .
C35 C 0.20953(19) 0.16517(14) 0.10075(8) 0.0214(3) Uani 1 1 d . . . . .
H35 H 0.302574 0.175430 0.064846 0.026 Uiso 1 1 calc R U . . .
C34 C 0.1685(2) 0.04557(14) 0.13160(9) 0.0279(3) Uani 1 1 d . . . . .
H34 H 0.233673 -0.025804 0.116666 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4676(2) 0.02394(15) 0.26840(7) 0.0259(3) Uani 1 1 d . . . . .
H10A H 0.558574 0.000483 0.232690 0.039 Uiso 1 1 calc R U . . .
H10B H 0.446145 0.115458 0.262349 0.039 Uiso 1 1 calc R U . . .
H10C H 0.365001 -0.009123 0.265025 0.039 Uiso 1 1 calc R U . . .
C29 C 0.53390(18) 0.30960(14) 0.13948(8) 0.0240(3) Uani 1 1 d . . . . .
H29A H 0.517269 0.252588 0.110868 0.036 Uiso 1 1 calc R U . . .
H29B H 0.592190 0.262168 0.177095 0.036 Uiso 1 1 calc R U . . .
H29C H 0.601973 0.373828 0.111673 0.036 Uiso 1 1 calc R U . . .
C33 C 0.0322(2) 0.03045(15) 0.18426(8) 0.0299(4) Uani 1 1 d . . . . .
H33 H 0.005075 -0.051171 0.205529 0.036 Uiso 1 1 calc R U . . .
C32 C -0.0638(2) 0.13476(16) 0.20563(8) 0.0267(3) Uani 1 1 d . . . . .
H32 H -0.157023 0.124437 0.241460 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2185(2) 0.40638(16) 0.56507(8) 0.0255(3) Uani 1 1 d . U . . .
H19A H 0.261452 0.339949 0.600641 0.038 Uiso 0.845(8) 1 calc R U P A 1
H19B H 0.129691 0.463247 0.586443 0.038 Uiso 0.845(8) 1 calc R U P A 1
H19C H 0.310568 0.453293 0.539403 0.038 Uiso 0.845(8) 1 calc R U P A 1
H19D H 0.238276 0.474969 0.525792 0.038 Uiso 0.155(8) 1 calc R U P A 2
H19E H 0.323118 0.376485 0.584206 0.038 Uiso 0.155(8) 1 calc R U P A 2
H19F H 0.131086 0.436511 0.600119 0.038 Uiso 0.155(8) 1 calc R U P A 2
C18 C 0.1467(2) 0.3484(2) 0.51653(15) 0.0201(5) Uani 0.845(8) 1 d D U P A 1
H18A H 0.062053 0.293374 0.542579 0.024 Uiso 0.845(8) 1 calc R U P A 1
H18B H 0.091415 0.414884 0.483521 0.024 Uiso 0.845(8) 1 calc R U P A 1
C01F C 0.1644(14) 0.3058(15) 0.5433(8) 0.0223(18) Uani 0.155(8) 1 d D U P A 2
H01A H 0.048935 0.330342 0.531939 0.027 Uiso 0.155(8) 1 calc R U P A 2
H01B H 0.163044 0.230886 0.580492 0.027 Uiso 0.155(8) 1 calc R U P A 2
H2 H 0.164(2) -0.0232(17) 0.4426(9) 0.022(4) Uiso 1 1 d . . . . .
H4 H 0.097(2) 0.4401(18) 0.0603(10) 0.026(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
O4 C17 1.2323(16) . ?
O8 C36 1.2345(15) . ?
O7 C36 1.3553(16) . ?
O7 C37 1.4481(16) . ?
O3 C17 1.3565(16) . ?
O3 C18 1.4525(19) . ?
O3 C01F 1.521(10) . ?
O6 N3 1.2302(15) . ?
O5 N3 1.2332(16) . ?
O1 N1 1.2326(16) . ?
O2 N1 1.2270(16) . ?
N4 C27 1.3624(16) . ?
N4 C30 1.4318(17) . ?
N4 H4 0.891(19) . ?
N2 C14 1.4289(17) . ?
N2 C8 1.3560(17) . ?
N2 H2 0.885(18) . ?
N3 C20 1.4694(16) . ?
N1 C1 1.4715(17) . ?
C36 C26 1.4466(18) . ?
C23 C22 1.4000(18) . ?
C23 C26 1.4962(17) . ?
C23 C24 1.3993(18) . ?
C4 C7 1.4958(17) . ?
C4 C5 1.4026(19) . ?
C4 C3 1.3975(18) . ?
C27 C26 1.3813(18) . ?
C27 C28 1.5092(18) . ?
C20 C21 1.3864(18) . ?
C20 C25 1.3886(19) . ?
C17 C7 1.4473(18) . ?
C1 C6 1.3900(19) . ?
C1 C2 1.385(2) . ?
C7 C8 1.3841(18) . ?
C30 C31 1.3943(19) . ?
C30 C35 1.390(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.3920(18) . ?
C14 C13 1.3928(19) . ?
C14 C15 1.3911(19) . ?
C6 H6 0.9500 . ?
C6 C5 1.3919(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.3929(18) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.391(2) . ?
C8 C9 1.5144(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.3890(19) . ?
C2 H2A 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.532(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3915(19) . ?
C31 H31 0.9500 . ?
C31 C32 1.392(2) . ?
C21 H21 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.387(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.509(2) . ?
C25 H25 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.534(2) . ?
C11 H11 0.9500 . ?
C11 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C35 H35 0.9500 . ?
C35 C34 1.394(2) . ?
C34 H34 0.9500 . ?
C34 C33 1.392(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C33 H33 0.9500 . ?
C33 C32 1.387(3) . ?
C32 H32 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
C19 C18 1.520(3) . ?
C19 C01F 1.432(11) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C01F H01A 0.9900 . ?
C01F H01B 0.9900 . ?

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
C36 O7 C37 116.27(10) . . ?
C17 O3 C18 117.64(12) . . ?
C17 O3 C01F 110.6(5) . . ?
C27 N4 C30 123.72(11) . . ?
C27 N4 H4 116.3(12) . . ?
C30 N4 H4 119.7(12) . . ?
C14 N2 H2 118.5(12) . . ?
C8 N2 C14 124.11(11) . . ?
C8 N2 H2 117.3(12) . . ?
O6 N3 O5 123.32(12) . . ?
O6 N3 C20 118.60(11) . . ?
O5 N3 C20 118.07(11) . . ?
O1 N1 C1 117.84(12) . . ?
O2 N1 O1 123.38(12) . . ?
O2 N1 C1 118.78(12) . . ?
O8 C36 O7 121.99(12) . . ?
O8 C36 C26 126.14(12) . . ?
O7 C36 C26 111.86(11) . . ?
C22 C23 C26 120.71(11) . . ?
C24 C23 C22 118.74(12) . . ?
C24 C23 C26 120.51(11) . . ?
C5 C4 C7 120.68(12) . . ?
C3 C4 C7 120.74(12) . . ?
C3 C4 C5 118.58(12) . . ?
N4 C27 C26 123.02(12) . . ?
N4 C27 C28 117.10(11) . . ?
C26 C27 C28 119.85(11) . . ?
C21 C20 N3 118.91(12) . . ?
C21 C20 C25 122.54(12) . . ?
C25 C20 N3 118.55(12) . . ?
O4 C17 O3 122.02(12) . . ?
O4 C17 C7 125.94(12) . . ?
O3 C17 C7 112.04(11) . . ?
C6 C1 N1 119.11(12) . . ?
C2 C1 N1 118.23(12) . . ?
C2 C1 C6 122.66(12) . . ?
C17 C7 C4 118.60(11) . . ?
C8 C7 C4 120.57(11) . . ?
C8 C7 C17 120.77(11) . . ?
C31 C30 N4 119.38(12) . . ?
C35 C30 N4 120.49(12) . . ?
C35 C30 C31 120.13(13) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 C23 121.02(12) . . ?
C21 C22 H22 119.5 . . ?
C36 C26 C23 118.55(11) . . ?
C27 C26 C36 121.68(11) . . ?
C27 C26 C23 119.71(11) . . ?
C13 C14 N2 119.53(12) . . ?
C15 C14 N2 120.23(12) . . ?
C15 C14 C13 120.24(12) . . ?
C1 C6 H6 121.0 . . ?
C1 C6 C5 118.07(13) . . ?
C5 C6 H6 121.0 . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.20(12) . . ?
C25 C24 H24 119.4 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.11(12) . . ?
C6 C5 H5 119.4 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.76(13) . . ?
C12 C13 H13 120.1 . . ?
N2 C8 C7 122.57(12) . . ?
N2 C8 C9 116.77(11) . . ?
C7 C8 C9 120.40(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.44(13) . . ?
C2 C3 H3 119.3 . . ?
C1 C2 C3 118.13(13) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C27 C28 C29 111.82(11) . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.62(13) . . ?
C16 C15 H15 120.2 . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.81(14) . . ?
C32 C31 H31 120.1 . . ?
C20 C21 C22 118.33(12) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.06(13) . . ?
C11 C12 H12 120.0 . . ?
O7 C37 H37A 110.2 . . ?
O7 C37 H37B 110.2 . . ?
O7 C37 C38 107.52(11) . . ?
H37A C37 H37B 108.5 . . ?
C38 C37 H37A 110.2 . . ?
C38 C37 H37B 110.2 . . ?
C20 C25 C24 118.09(12) . . ?
C20 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.91(12) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C16 120.11(13) . . ?
C16 C11 H11 119.9 . . ?
C15 C16 H16 119.9 . . ?
C11 C16 C15 120.18(14) . . ?
C11 C16 H16 119.9 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C30 C35 H35 120.1 . . ?
C30 C35 C34 119.75(14) . . ?
C34 C35 H35 120.1 . . ?
C35 C34 H34 119.9 . . ?
C33 C34 C35 120.16(15) . . ?
C33 C34 H34 119.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C34 C33 H33 120.1 . . ?
C32 C33 C34 119.89(14) . . ?
C32 C33 H33 120.1 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.25(15) . . ?
C33 C32 H32 119.9 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19D C19 H19E 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
C01F C19 H19D 109.5 . . ?
C01F C19 H19E 109.5 . . ?
C01F C19 H19F 109.5 . . ?
O3 C18 C19 107.57(15) . . ?
O3 C18 H18A 110.2 . . ?
O3 C18 H18B 110.2 . . ?
C19 C18 H18A 110.2 . . ?
C19 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
O3 C01F H01A 110.0 . . ?
O3 C01F H01B 110.0 . . ?
C19 C01F O3 108.6(7) . . ?
C19 C01F H01A 110.0 . . ?
C19 C01F H01B 110.0 . . ?
H01A C01F H01B 108.3 . . ?

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
O4 C17 C7 C4 177.32(13) . . . . ?
O4 C17 C7 C8 0.1(2) . . . . ?
O8 C36 C26 C23 179.53(12) . . . . ?
O8 C36 C26 C27 -3.3(2) . . . . ?
O7 C36 C26 C23 -1.35(16) . . . . ?
O7 C36 C26 C27 175.83(11) . . . . ?
O3 C17 C7 C4 -3.39(17) . . . . ?
O3 C17 C7 C8 179.43(12) . . . . ?
O6 N3 C20 C21 -177.15(13) . . . . ?
O6 N3 C20 C25 3.23(19) . . . . ?
O5 N3 C20 C21 2.37(19) . . . . ?
O5 N3 C20 C25 -177.25(13) . . . . ?
O1 N1 C1 C6 -178.47(13) . . . . ?
O1 N1 C1 C2 0.94(18) . . . . ?
O2 N1 C1 C6 1.03(19) . . . . ?
O2 N1 C1 C2 -179.56(13) . . . . ?
N4 C27 C26 C36 4.07(19) . . . . ?
N4 C27 C26 C23 -178.78(12) . . . . ?
N4 C27 C28 C29 94.93(14) . . . . ?
N4 C30 C31 C32 -179.04(12) . . . . ?
N4 C30 C35 C34 179.44(13) . . . . ?
N2 C14 C13 C12 178.73(12) . . . . ?
N2 C14 C15 C16 -177.91(12) . . . . ?
N2 C8 C9 C10 83.53(15) . . . . ?
N3 C20 C21 C22 -178.26(12) . . . . ?
N3 C20 C25 C24 177.73(12) . . . . ?
N1 C1 C6 C5 178.15(12) . . . . ?
N1 C1 C2 C3 -178.37(12) . . . . ?
C36 O7 C37 C38 -169.52(11) . . . . ?
C23 C22 C21 C20 1.1(2) . . . . ?
C23 C24 C25 C20 -0.1(2) . . . . ?
C4 C7 C8 N2 -177.96(12) . . . . ?
C4 C7 C8 C9 -4.04(19) . . . . ?
C4 C3 C2 C1 0.1(2) . . . . ?
C27 N4 C30 C31 93.60(16) . . . . ?
C27 N4 C30 C35 -86.74(17) . . . . ?
C17 O3 C18 C19 145.93(15) . . . . ?
C17 O3 C01F C19 171.0(8) . . . . ?
C17 C7 C8 N2 -0.8(2) . . . . ?
C17 C7 C8 C9 173.08(12) . . . . ?
C1 C6 C5 C4 0.3(2) . . . . ?
C7 C4 C5 C6 -178.95(12) . . . . ?
C7 C4 C3 C2 178.73(12) . . . . ?
C7 C8 C9 C10 -90.73(15) . . . . ?
C30 N4 C27 C26 -177.71(12) . . . . ?
C30 N4 C27 C28 4.21(18) . . . . ?
C30 C31 C32 C33 -0.8(2) . . . . ?
C30 C35 C34 C33 0.0(2) . . . . ?
C22 C23 C26 C36 96.88(15) . . . . ?
C22 C23 C26 C27 -80.36(16) . . . . ?
C22 C23 C24 C25 2.4(2) . . . . ?
C26 C23 C22 C21 174.56(13) . . . . ?
C26 C23 C24 C25 -175.11(13) . . . . ?
C26 C27 C28 C29 -83.21(15) . . . . ?
C14 N2 C8 C7 -179.27(12) . . . . ?
C14 N2 C8 C9 6.60(19) . . . . ?
C14 C13 C12 C11 -0.3(2) . . . . ?
C14 C15 C16 C11 -1.3(2) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C24 C23 C22 C21 -3.0(2) . . . . ?
C24 C23 C26 C36 -85.64(16) . . . . ?
C24 C23 C26 C27 97.12(15) . . . . ?
C5 C4 C7 C17 -72.02(16) . . . . ?
C5 C4 C7 C8 105.17(15) . . . . ?
C5 C4 C3 C2 -1.0(2) . . . . ?
C13 C14 C15 C16 2.3(2) . . . . ?
C13 C12 C11 C16 1.3(2) . . . . ?
C8 N2 C14 C13 -105.89(15) . . . . ?
C8 N2 C14 C15 74.31(18) . . . . ?
C3 C4 C7 C17 108.30(15) . . . . ?
C3 C4 C7 C8 -74.51(17) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C28 C27 C26 C36 -177.90(11) . . . . ?
C28 C27 C26 C23 -0.75(18) . . . . ?
C15 C14 C13 C12 -1.5(2) . . . . ?
C31 C30 C35 C34 -0.9(2) . . . . ?
C21 C20 C25 C24 -1.9(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C37 O7 C36 O8 4.25(18) . . . . ?
C37 O7 C36 C26 -174.91(11) . . . . ?
C25 C20 C21 C22 1.3(2) . . . . ?
C35 C30 C31 C32 1.3(2) . . . . ?
C35 C34 C33 C32 0.6(2) . . . . ?
C34 C33 C32 C31 -0.2(2) . . . . ?
C18 O3 C17 O4 -12.4(2) . . . . ?
C18 O3 C17 C7 168.31(17) . . . . ?
C01F O3 C17 O4 14.4(8) . . . . ?
C01F O3 C17 C7 -164.9(7) . . . . ?

_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 1.228
_oxdiff_exptl_absorpt_empirical_full_min 0.714
