# 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_2022ncs0045z
_database_code_depnum_ccdc_archive 'CCDC 2303290'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2023-12-01 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_2022ncs0045z        
;
PROBLEM: D-H Bond Without Acceptor  O10      --H10A     .     Please Check 
RESPONSE: Not all residual solvent (water) could be modelled. Solvent which could not be modelled was treated with the olex implementation of SQUEEZE.
;
# end Validation Reply Form
_audit_creation_date             2023-11-30
_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         'C15 H5 N O6, 3(H2 O), C8 H12 N4, O, 4.5[H2O]'
_chemical_formula_sum            'C23 H32 N5 O14.50'
_chemical_formula_weight         610.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.08760(10)
_cell_length_b                   9.07010(10)
_cell_length_c                   22.17710(10)
_cell_angle_alpha                93.4340(10)
_cell_angle_beta                 95.1770(10)
_cell_angle_gamma                94.8900(10)
_cell_volume                     1411.39(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.7530
_cell_measurement_theta_min      1.9920
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_preparation       'see experimental'
_exptl_crystal_recrystallization_method 'see experimental'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47656
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.144
_diffrn_reflns_theta_min         2.005
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   0.00   0.50    1.00    --  -46.61 105.00  48.00  166
  2  ω      6.00  83.00   0.50    1.00    --   46.61-105.00 -51.00  154
  3  ω     29.00 107.00   0.50    4.00    --  101.75-105.00 -51.00  156
  4  ω   -107.00 -30.00   0.50    4.00    -- -103.00 105.00  48.00  154
  5  ω   -174.00 -86.00   0.50    4.00    -- -103.00-105.00 -51.00  176
  6  ω    -40.00  27.00   0.50    1.00    --  -46.61  37.00-150.00  134
  7  ω    -24.00  29.00   0.50    1.00    --  -46.61  19.00 -60.00  106
  8  ω    -24.00  29.00   0.50    1.00    --  -46.61  19.00 -30.00  106
  9  ω     24.00 118.00   0.50    1.00    --   46.61  77.00  60.00  188
 10  ω    -25.00  62.00   0.50    1.00    --   46.61 -57.00-180.00  174
 11  ω    -25.00  69.00   0.50    1.00    --   46.61 -77.00  90.00  188
 12  ω     29.00 106.00   0.50    4.00    --  101.75 -94.00-150.00  154
 13  ω     29.00 106.00   0.50    4.00    --  101.75 -94.00 120.00  154
 14  ω     29.00  73.00   0.50    4.00    --  101.75 -61.00 120.00   88
 15  ω     29.00  73.00   0.50    4.00    --  101.75 -61.00-150.00   88
 16  ω     29.00 112.00   0.50    4.00    --  101.75-125.00 120.00  166
 17  ω     79.00 175.00   0.50    4.00    --  101.75  77.00-180.00  192
 18  ω     29.00 108.00   0.50    4.00    --  101.75 -77.00 120.00  158
 19  ω     29.00 108.00   0.50    4.00    --  101.75 -77.00 -60.00  158
 20  ω     82.00 175.00   0.50    4.00    --  101.75 125.00   0.00  186
 21  ω     29.00 112.00   0.50    4.00    --  101.75-125.00 -60.00  166
 22  ω     92.00 175.00   0.50    4.00    --  101.75 105.00  48.00  166
 23  ω     29.00  73.00   0.50    4.00    --  101.75 -61.00-180.00   88
 24  ω     29.00 106.00   0.50    4.00    --  101.75 -94.00 -60.00  154
 25  ω     29.00  73.00   0.50    4.00    --  101.75 -61.00   0.00   88
 26  ω   -104.00 -30.00   0.50    4.00    -- -103.00  77.00-180.00  148
 27  ω   -174.00 -83.00   0.50    4.00    -- -103.00 -69.00  29.68  182
 28  ω   -174.00 -89.00   0.50    4.00    -- -103.00 -51.00 -18.37  170
 29  ω   -174.00 -89.00   0.50    4.00    -- -103.00 -54.00 -33.19  170
 30  ω   -112.00 -30.00   0.50    4.00    -- -103.00 125.00  60.00  164
 31  ω     24.00 118.00   0.50    1.00    --   46.61  77.00 -90.00  188
 32  ω     32.00 118.00   0.50    1.00    --   46.61  57.00   0.00  172
 33  ω     32.00 118.00   0.50    1.00    --   46.61  57.00-120.00  172
 34  ω     32.00 118.00   0.50    1.00    --   46.61  57.00 150.00  172
 35  ω     24.00 118.00   0.50    1.00    --   46.61  77.00 150.00  188
 36  ω     24.00  53.00   0.50    1.00    --   46.61  77.00-180.00   58
 37  ω    -55.00 -24.00   0.50    1.00    --  -46.61 -77.00   0.00   62
 38  ω    -60.00 -33.00   0.50    1.00    --  -46.61 -57.00 150.00   54
 39  ω    -55.00 -24.00   0.50    1.00    --  -46.61 -77.00  60.00   62
 40  ω    -81.00 -34.00   0.50    1.00    --  -46.61 -37.00 -90.00   94
 41  ω    -67.00 -34.00   0.50    1.00    --  -46.61 -37.00 120.00   66
 42  ω    -60.00 -33.00   0.50    1.00    --  -46.61 -57.00-150.00   54
 43  ω     91.00 119.00   0.50    1.00    --   46.61  37.00 -60.00   56
 44  ω     53.00  79.00   0.50    1.00    --   46.61  37.00 -60.00   52
 45  ω     26.00  54.00   0.50    1.00    --   46.61  77.00  90.00   56
 46  ω     28.00  54.00   0.50    1.00    --   46.61  77.00-150.00   52
 47  ω     25.00  51.00   0.50    1.00    --   46.61  77.00 -30.00   52
 48  ω     35.00  89.00   0.50    1.00    --   46.61  19.00  30.00  108
 49  ω     24.00  50.00   0.50    1.00    --   46.61  77.00-120.00   52
 50  ω     25.00  69.00   0.50    1.00    --   46.61  77.00   0.00   88
 51  ω   -109.00 -82.00   0.50    4.00    -- -103.00 -74.00 -24.17   54
 52  ω   -147.00 -86.00   0.50    4.00    -- -103.00 -66.00 131.08  122
 53  ω   -172.00-146.00   0.50    4.00    -- -103.00 -81.00-115.87   52
 54  ω   -117.00 -86.00   0.50    4.00    -- -103.00 -67.00  47.27   62
 55  ω   -170.00-128.00   0.50    4.00    -- -103.00 -67.00  47.27   84
 56  ω   -107.00 -80.00   0.50    4.00    -- -103.00 -77.00 120.00   54
 57  ω   -173.00-140.00   0.50    4.00    -- -103.00 -74.00 -88.49   66
 58  ω   -115.00 -86.00   0.50    4.00    -- -103.00 -61.00 -90.00   58
 59  ω   -109.00 -84.00   0.50    4.00    -- -103.00 -68.00 -52.64   50
 60  ω   -149.00 -83.00   0.50    4.00    -- -103.00 -70.00-112.86  132
 61  ω   -107.00 -81.00   0.50    4.00    -- -103.00 -77.00-180.00   52
 62  ω   -106.00 -80.00   0.50    4.00    -- -103.00 -76.00  -3.91   52
 63  ω   -160.00-134.00   0.50    4.00    -- -103.00 -61.00  60.00   52
 64  ω   -111.00 -86.00   0.50    4.00    -- -103.00 -61.00  60.00   50
 65  ω   -107.00 -81.00   0.50    4.00    -- -103.00 -77.00  30.00   52
 66  ω   -174.00 -81.00   0.50    4.00    -- -103.00 -78.00-148.85  186
 67  ω   -143.00-117.00   0.50    4.00    -- -103.00 -61.00 -90.00   52
 68  ω   -105.00 -78.00   0.50    4.00    -- -103.00 -82.00 137.22   54
 69  ω   -138.00 -84.00   0.50    4.00    -- -103.00 -68.00 140.78  108
 70  ω   -158.00 -87.00   0.50    4.00    -- -103.00 -61.00 150.00  142
 71  ω   -110.00 -84.00   0.50    4.00    -- -103.00 -68.00 -39.93   52
 72  ω   -114.00 -87.00   0.50    4.00    -- -103.00 -61.00 -30.00   54
 73  ω   -106.00 -80.00   0.50    4.00    -- -103.00 -79.00 161.01   52
 74  ω   -105.00 -80.00   0.50    4.00    -- -103.00 -77.00 -95.02   50
 75  ω   -110.00 -84.00   0.50    4.00    -- -103.00 -68.00 -58.99   52
 76  ω   -166.00-139.00   0.50    4.00    -- -103.00 -79.00 161.01   54
 77  ω   -108.00 -83.00   0.50    4.00    -- -103.00 -69.00  55.45   50
 78  ω   -129.00 -91.00   0.50    4.00    -- -103.00 -48.00  -8.47   76
 79  ω   -106.00 -80.00   0.50    4.00    -- -103.00 -77.00  45.42   52
 80  ω   -111.00 -86.00   0.50    4.00    -- -103.00 -61.00  90.00   50
 81  ω   -107.00 -80.00   0.50    4.00    -- -103.00 -78.00-113.42   54
 82  ω   -105.00 -79.00   0.50    4.00    -- -103.00 -80.00 100.99   52
 83  ω   -170.00-120.00   0.50    4.00    -- -103.00 -80.00-160.96  100
 84  ω   -108.00 -80.00   0.50    4.00    -- -103.00 -80.00-160.96   56
 85  ω   -164.00-137.00   0.50    4.00    -- -103.00 -61.00  90.00   54
 86  ω   -105.00 -79.00   0.50    4.00    -- -103.00 -81.00-115.87   52
 87  ω   -107.00 -81.00   0.50    4.00    -- -103.00 -75.00-141.01   52
 88  ω   -116.00 -86.00   0.50    4.00    -- -103.00 -64.00  77.65   60
 89  ω   -115.00 -85.00   0.50    4.00    -- -103.00 -66.00 172.34   60
 90  ω   -107.00 -81.00   0.50    4.00    -- -103.00 -74.00 -88.49   52
 91  ω   -109.00 -79.00   0.50    4.00    -- -103.00 -80.00-128.03   60
 92  ω   -109.00 -82.00   0.50    4.00    -- -103.00 -77.00 -60.00   54
 93  ω   -120.00 -34.00   0.50    1.00    --  -46.61 -37.00-180.00  172
 94  ω   -121.00 -34.00   0.50    1.00    --  -46.61 -19.00 -60.00  174
 95  ω   -118.00 -24.00   0.50    1.00    --  -46.61 -77.00  60.00  188
 96  ω   -118.00 -32.00   0.50    1.00    --  -46.61 -57.00 -90.00  172
 97  ω     24.00 118.00   0.50    1.00    --   46.61  77.00-150.00  188
 98  ω    -26.00  44.00   0.50    1.00    --   46.61 -37.00 -60.00  140
 99  ω     24.00 118.00   0.50    1.00    --   46.61  77.00   0.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5071
_reflns_number_total             5703
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (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         0.532
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.039
_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)+(0.0918P)²+0.8735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1670
_refine_special_details          
'Non-hydrogen atoms were refined anisotropically. Hydrogen atoms were placed in geometrically calculated positions, with the exception of hydrogen atoms on oxygen atoms O9 and O9A which belong to a disordered water molecule and are not included in the model. Modelling hydrogen atoms on O9 and O9A resulted in a model where the shift did not settle. Only a part of the water could be sensibly modelled. Given the data had to be collected at room temperature, it is unsuprising that the water molecules that could be modelled are directly hydrogen bonded to the framework. The rest of the residual water in the voids of this structure (grown from aqueous solution) was treated with a solvent mask using the olex implementation of SQUEEZE.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Sof(O9A)=1-FVAR(1)
 Sof(O9)=FVAR(1)
 Fixed Sof: O11(0.5) H11A(0.5) H11B(0.5) O7(0.5) H7A(0.5) H7B(0.5)
3.a Free rotating group:
 O8(H8A,H8B), O10(H10A,H10B), O11(H11A,H11B), O7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C16(H16), C19(H19), C22(H22), C3(H3), C4(H4), C6(H6),
 C7(H7)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B)
;
_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
O1 O 0.3304(2) 0.14489(13) 0.34720(6) 0.0375(3) Uani 1 1 d . . . . .
O2 O 0.2975(3) 0.16788(16) 0.24821(7) 0.0585(5) Uani 1 1 d . . . . .
O3 O 0.1123(2) -0.35219(15) 0.42369(6) 0.0410(3) Uani 1 1 d . . . . .
O4 O -0.0102(2) -0.53130(14) 0.35533(6) 0.0405(3) Uani 1 1 d . . . . .
O5 O -0.2034(2) -0.24234(18) 0.13965(6) 0.0473(4) Uani 1 1 d . . . . .
O6 O 0.3676(2) -0.43397(17) 0.15971(6) 0.0422(3) Uani 1 1 d . . . . .
N5 N 0.0798(2) -0.34077(16) 0.14974(6) 0.0316(3) Uani 1 1 d . . . . .
C9 C 0.2851(3) 0.0934(2) 0.29427(8) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.0662(3) -0.40358(19) 0.36978(8) 0.0299(4) Uani 1 1 d . . . . .
C11 C 0.2106(3) -0.06811(18) 0.28252(8) 0.0296(4) Uani 1 1 d . . . . .
C12 C 0.1794(3) -0.12932(19) 0.22317(8) 0.0324(4) Uani 1 1 d . . . . .
H12 H 0.203748 -0.071349 0.191063 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1117(3) -0.27715(19) 0.21206(8) 0.0302(4) Uani 1 1 d . . . . .
C14 C 0.0739(2) -0.36505(18) 0.25903(8) 0.0278(4) Uani 1 1 d . . . . .
H14 H 0.026623 -0.463738 0.250797 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1067(2) -0.30543(18) 0.31881(7) 0.0267(3) Uani 1 1 d . . . . .
C16 C 0.1758(2) -0.15666(18) 0.33017(7) 0.0265(3) Uani 1 1 d . . . . .
H16 H 0.198745 -0.116298 0.369976 0.032 Uiso 1 1 calc R U . . .
C17 C -0.0892(3) -0.3155(2) 0.11664(8) 0.0365(4) Uani 1 1 d . . . . .
C18 C -0.1205(3) -0.3810(2) 0.05307(8) 0.0371(4) Uani 1 1 d . . . . .
C19 C -0.2827(3) -0.3584(3) 0.01735(9) 0.0482(5) Uani 1 1 d . . . . .
H19 H -0.371590 -0.300196 0.032647 0.058 Uiso 1 1 calc R U . . .
C20 C 0.2212(3) -0.4218(2) 0.12819(8) 0.0342(4) Uani 1 1 d . . . . .
C21 C 0.1844(3) -0.4905(2) 0.06547(8) 0.0357(4) Uani 1 1 d . . . . .
C22 C 0.3145(3) -0.5767(3) 0.04240(9) 0.0472(5) Uani 1 1 d . . . . .
H22 H 0.424532 -0.592413 0.066407 0.057 Uiso 1 1 calc R U . . .
C23 C 0.0164(3) -0.4676(2) 0.03014(8) 0.0332(4) Uani 1 1 d . . . . .
O8 O 1.3016(3) 1.1619(2) 0.46658(7) 0.0709(6) Uani 1 1 d G . . . .
H8A H 1.274029 1.249726 0.474909 0.106 Uiso 1 1 d G U . . .
H8B H 1.308447 1.156750 0.428477 0.106 Uiso 1 1 d G U . . .
O10 O 0.5819(4) 1.1460(3) 0.17825(10) 0.0911(7) Uani 1 1 d G . . . .
H10A H 0.517774 1.158266 0.144926 0.137 Uiso 1 1 d G U . . .
H10B H 0.662426 1.086530 0.168600 0.137 Uiso 1 1 d G U . . .
N1 N 0.8672(3) 1.19784(17) 0.39495(7) 0.0408(4) Uani 1 1 d . . . . .
H1A H 0.915425 1.288530 0.397333 0.049 Uiso 1 1 calc R U . . .
H1B H 0.860692 1.150710 0.427320 0.049 Uiso 1 1 calc R U . . .
N2 N 0.8149(3) 1.20476(18) 0.29330(8) 0.0426(4) Uani 1 1 d . . . . .
H2A H 0.863180 1.295431 0.295905 0.051 Uiso 1 1 calc R U . . .
H2B H 0.773436 1.161676 0.258447 0.051 Uiso 1 1 calc R U . . .
N3 N 0.5263(2) 0.44136(17) 0.37663(8) 0.0370(4) Uani 1 1 d . . . . .
H3A H 0.481779 0.349761 0.374345 0.044 Uiso 1 1 calc R U . . .
H3B H 0.574316 0.483914 0.410935 0.044 Uiso 1 1 calc R U . . .
N4 N 0.4484(2) 0.45366(17) 0.27526(8) 0.0388(4) Uani 1 1 d . . . . .
H4A H 0.403463 0.362139 0.272337 0.047 Uiso 1 1 calc R U . . .
H4B H 0.445746 0.504009 0.243598 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8044(3) 1.13212(19) 0.34251(8) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.7249(2) 0.97445(18) 0.33778(8) 0.0291(4) Uani 1 1 d . . . . .
C3 C 0.7163(3) 0.88895(19) 0.28319(8) 0.0311(4) Uani 1 1 d . . . . .
H3 H 0.754538 0.931895 0.248717 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6510(3) 0.74046(19) 0.28004(8) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.645355 0.683799 0.243451 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5938(3) 0.67544(18) 0.33153(8) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.5982(3) 0.7614(2) 0.38570(8) 0.0339(4) Uani 1 1 d . . . . .
H6 H 0.557599 0.718799 0.419957 0.041 Uiso 1 1 calc R U . . .
C7 C 0.6627(3) 0.9102(2) 0.38887(8) 0.0326(4) Uani 1 1 d . . . . .
H7 H 0.664530 0.967485 0.425159 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5208(3) 0.51616(19) 0.32778(9) 0.0328(4) Uani 1 1 d . . . . .
O9 O 0.6878(15) 0.5081(10) 0.4965(3) 0.050(3) Uani 0.263(11) 1 d . . P A 1
O11 O 0.9519(5) 1.0897(4) 0.51075(13) 0.0531(8) Uani 0.5 1 d G . P B 1
H11A H 0.876093 1.017384 0.518914 0.080 Uiso 0.5 1 d G U P B 1
H11B H 0.927196 1.161896 0.534020 0.080 Uiso 0.5 1 d G U P B 1
O7 O 0.6965(6) 1.1314(4) 0.50731(14) 0.0589(9) Uani 0.5 1 d G . P C 2
H7A H 0.764536 1.160903 0.479991 0.088 Uiso 0.5 1 d G U P C 2
H7B H 0.590555 1.166564 0.499148 0.088 Uiso 0.5 1 d G U P C 2
O9A O 0.7874(6) 0.5599(3) 0.48923(9) 0.0458(11) Uani 0.737(11) 1 d . . P A 2


_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 C9 1.241(2) . ?
O2 C9 1.263(2) . ?
O3 C10 1.261(2) . ?
O4 C10 1.247(2) . ?
O5 C17 1.217(2) . ?
O6 C20 1.214(2) . ?
N5 C13 1.456(2) . ?
N5 C17 1.391(3) . ?
N5 C20 1.394(3) . ?
C9 C11 1.514(2) . ?
C10 C15 1.513(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.392(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(2) . ?
C13 C14 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(2) . ?
C15 C16 1.396(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.487(2) . ?
C18 C19 1.373(3) . ?
C18 C23 1.410(3) . ?
C19 H19 0.9300 . ?
C19 C22 1.408(3) 2_545 ?
C20 C21 1.481(2) . ?
C21 C22 1.373(3) . ?
C21 C23 1.403(3) . ?
C22 H22 0.9300 . ?
C23 C23 1.419(3) 2_545 ?
O8 H8A 0.8502 . ?
O8 H8B 0.8496 . ?
O10 H10A 0.8503 . ?
O10 H10B 0.8503 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.298(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.313(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C8 1.312(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C8 1.305(2) . ?
C1 C2 1.486(2) . ?
C2 C3 1.392(2) . ?
C2 C7 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(3) . ?
C5 C6 1.389(3) . ?
C5 C8 1.487(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(2) . ?
C7 H7 0.9300 . ?
O11 H11A 0.8502 . ?
O11 H11B 0.8495 . ?
O7 H7A 0.8493 . ?
O7 H7B 0.8497 . ?

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
C17 N5 C13 117.29(15) . . ?
C17 N5 C20 125.43(15) . . ?
C20 N5 C13 117.28(15) . . ?
O1 C9 O2 124.00(16) . . ?
O1 C9 C11 119.48(16) . . ?
O2 C9 C11 116.52(16) . . ?
O3 C10 C15 118.46(15) . . ?
O4 C10 O3 124.31(16) . . ?
O4 C10 C15 117.23(15) . . ?
C12 C11 C9 119.30(16) . . ?
C12 C11 C16 119.56(15) . . ?
C16 C11 C9 121.14(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.64(16) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 N5 119.38(15) . . ?
C14 C13 N5 119.49(15) . . ?
C14 C13 C12 121.13(15) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.78(15) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 119.13(14) . . ?
C14 C15 C16 119.22(15) . . ?
C16 C15 C10 121.65(14) . . ?
C11 C16 C15 120.66(15) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O5 C17 N5 120.29(16) . . ?
O5 C17 C18 122.84(18) . . ?
N5 C17 C18 116.87(17) . . ?
C19 C18 C17 120.06(19) . . ?
C19 C18 C23 120.47(17) . . ?
C23 C18 C17 119.46(17) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C22 120.1(2) . 2_545 ?
C22 C19 H19 120.0 2_545 . ?
O6 C20 N5 120.95(16) . . ?
O6 C20 C21 122.17(18) . . ?
N5 C20 C21 116.87(16) . . ?
C22 C21 C20 119.77(18) . . ?
C22 C21 C23 120.43(17) . . ?
C23 C21 C20 119.80(18) . . ?
C19 C22 H22 119.7 2_545 . ?
C21 C22 C19 120.50(19) . 2_545 ?
C21 C22 H22 119.7 . . ?
C18 C23 C23 119.1(2) . 2_545 ?
C21 C23 C18 121.51(16) . . ?
C21 C23 C23 119.4(2) . 2_545 ?
H8A O8 H8B 104.5 . . ?
H10A O10 H10B 104.5 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
N1 C1 N2 119.66(16) . . ?
N1 C1 C2 120.40(16) . . ?
N2 C1 C2 119.92(16) . . ?
C3 C2 C1 120.68(16) . . ?
C3 C2 C7 119.53(15) . . ?
C7 C2 C1 119.77(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.22(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.17(16) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C8 120.05(16) . . ?
C6 C5 C4 119.68(16) . . ?
C6 C5 C8 120.23(16) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.21(17) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.15(17) . . ?
C6 C7 H7 119.9 . . ?
N3 C8 C5 120.36(16) . . ?
N4 C8 N3 120.97(16) . . ?
N4 C8 C5 118.66(16) . . ?
H11A O11 H11B 104.5 . . ?
H7A O7 H7B 104.6 . . ?

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 C9 C11 C12 -173.16(18) . . . . ?
O1 C9 C11 C16 5.9(3) . . . . ?
O2 C9 C11 C12 6.6(3) . . . . ?
O2 C9 C11 C16 -174.37(19) . . . . ?
O3 C10 C15 C14 173.78(17) . . . . ?
O3 C10 C15 C16 -6.3(3) . . . . ?
O4 C10 C15 C14 -5.8(3) . . . . ?
O4 C10 C15 C16 174.12(17) . . . . ?
O5 C17 C18 C19 0.8(3) . . . . ?
O5 C17 C18 C23 -178.41(19) . . . . ?
O6 C20 C21 C22 3.0(3) . . . . ?
O6 C20 C21 C23 -177.26(18) . . . . ?
N5 C13 C14 C15 179.09(16) . . . . ?
N5 C17 C18 C19 -178.88(19) . . . . ?
N5 C17 C18 C23 1.9(3) . . . . ?
N5 C20 C21 C22 -177.36(19) . . . . ?
N5 C20 C21 C23 2.4(3) . . . . ?
C9 C11 C12 C13 179.84(17) . . . . ?
C9 C11 C16 C15 179.85(16) . . . . ?
C10 C15 C16 C11 -179.50(16) . . . . ?
C11 C12 C13 N5 -179.82(17) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 N5 C17 O5 0.3(3) . . . . ?
C13 N5 C17 C18 -179.98(15) . . . . ?
C13 N5 C20 O6 -2.5(3) . . . . ?
C13 N5 C20 C21 177.91(15) . . . . ?
C13 C14 C15 C10 -179.45(16) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C17 N5 C13 C12 -81.3(2) . . . . ?
C17 N5 C13 C14 98.7(2) . . . . ?
C17 N5 C20 O6 177.43(18) . . . . ?
C17 N5 C20 C21 -2.2(3) . . . . ?
C17 C18 C19 C22 -178.5(2) . . . 2_545 ?
C17 C18 C23 C21 -1.7(3) . . . . ?
C17 C18 C23 C23 178.6(2) . . . 2_545 ?
C19 C18 C23 C21 179.1(2) . . . . ?
C19 C18 C23 C23 -0.6(3) . . . 2_545 ?
C20 N5 C13 C12 98.7(2) . . . . ?
C20 N5 C13 C14 -81.4(2) . . . . ?
C20 N5 C17 O5 -179.61(18) . . . . ?
C20 N5 C17 C18 0.1(3) . . . . ?
C20 C21 C22 C19 -179.3(2) . . . 2_545 ?
C20 C21 C23 C18 -0.5(3) . . . . ?
C20 C21 C23 C23 179.22(19) . . . 2_545 ?
C22 C21 C23 C18 179.23(19) . . . . ?
C22 C21 C23 C23 -1.1(3) . . . 2_545 ?
C23 C18 C19 C22 0.7(3) . . . 2_545 ?
C23 C21 C22 C19 1.0(3) . . . 2_545 ?
N1 C1 C2 C3 -158.46(18) . . . . ?
N1 C1 C2 C7 19.9(3) . . . . ?
N2 C1 C2 C3 20.2(3) . . . . ?
N2 C1 C2 C7 -161.48(19) . . . . ?
C1 C2 C3 C4 176.71(17) . . . . ?
C1 C2 C7 C6 -176.46(17) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C2 C7 C6 1.9(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C3 C4 C5 C8 179.03(16) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C4 C5 C8 N3 157.21(18) . . . . ?
C4 C5 C8 N4 -24.0(3) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C6 C5 C8 N3 -25.4(3) . . . . ?
C6 C5 C8 N4 153.44(19) . . . . ?
C7 C2 C3 C4 -1.7(3) . . . . ?
C8 C5 C6 C7 -178.76(17) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 89 electrons were 
found in a volume of 279Å³ in 1 void per unit cell. 
This is consistent with the presence of 
4.5[H2O] per Asymmetric Unit 
which account for 90 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.693 0.000 0.000 278.7 89.0 '9 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
;
####################################################################### 
# 
# 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_83685377_shelxt
_database_code_depnum_ccdc_archive 'CCDC 2303292'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2023-12-01 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_83685377_shelxt     
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        17% Check 
RESPONSE: Weakly diffracting, poor quality crystal. No alternative crystals availbale (see experimental). Solution provided for connectivity purposes
;
_vrf_PLAT029_83685377_shelxt     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.706 Why?  
RESPONSE: Weakly diffracting, poor quality crystal. No alternative crystals availbale (see experimental). Solution provided for connectivity purposes
;
_vrf_PLAT201_83685377_shelxt     
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         45 Report
RESPONSE: Weakly diffracting, poor quality crystal. Data quality does not support anisotropic refinement.
;
# end Validation Reply Form
_audit_creation_date             2023-11-29
_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        HOF_C
_chemical_formula_moiety         
'C30 H11 N2 O13, C4 H3 N O, 5(O), 2.5(C8 H12 N4), 17[H2O]'
_chemical_formula_sum            'C54 H78 N13 O36'
_chemical_formula_weight         1485.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0015 '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 0.0037 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0057 '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                   7.8430(4)
_cell_length_b                   19.3052(12)
_cell_length_c                   23.3588(7)
_cell_angle_alpha                88.568(5)
_cell_angle_beta                 81.294(4)
_cell_angle_gamma                86.534(5)
_cell_volume                     3489.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.208
_cell_measurement_theta_min      0.855
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1562
_exptl_crystal_preparation       'See experimental section'
_exptl_crystal_recrystallization_method 'See experimental section'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1969
_diffrn_reflns_av_unetI/netI     0.6103
_diffrn_reflns_Laue_measured_fraction_full 0.706
_diffrn_reflns_Laue_measured_fraction_max 0.706
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14538
_diffrn_reflns_point_group_measured_fraction_full 0.706
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        24.208
_diffrn_reflns_theta_max         24.208
_diffrn_reflns_theta_min         0.855
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.706
_diffrn_measured_fraction_theta_max 0.706
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_special_details          
'Structure provided for connectivity purposes only due to poor data quality.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1488
_reflns_number_total             8715
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.595
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         8715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3195
_refine_ls_R_factor_gt           0.1372
_refine_ls_restrained_S_all      0.802
_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)+(0.1312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3187
_refine_ls_wR_factor_ref         0.3727
_refine_special_details          
;
This data set is of poor data quality. The structure is only provided for connectivity purposes and to serve as a warning of the potential complexity of such systems, particularly when crystals are grown over long periods (such as those afforded by a pandemic) allowing multiple reaction processes to occur (see publication text for further details). Due to the long period of time over which this crystal was grown, repeat collections are not possible.
The crystal diffracted weakly with a low-resolution diffraction limit. Atoms were refined isotopically as the data quality does not support anisotropic refinement. Hydrogens were placed in geometrically calculated positions on the organic fragments. Some oxygen atoms of residual water molecules could be sensibly modelled, although adding hydrogens resulted in a model which did not settle. Remaining water was treated with the Olex implementation of SQUEEZE.
;
_olex2_refinement_description    
;
1.a Rotating group:
 N11(H11A), N9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C7(H7), C3(H3), C11(H11), C12(H12), C16(H16), C18(H18),
 C26(H26), C30(H30), C28(H28), C53(H53), C54(H54), C35(H35), C39(H39), C38(H38),
  C36(H36), C46(H46), C47(H47), C43(H43), C44(H44), C51(H51), C52(H52)
1.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C21(C10,C9,N1,C20,C19), C27(C26,C25,C30,C29,C28), C35(C34,
 C39,C38,C37,C36), C46(C47,C42,C43,C44,C45)
1.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B), N7(H7A,H7B), N8(H8A,H8B),
 N10(H10A,H10B), N12(H12A,H12B), N13(H13A,H13B)
;
_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
O1 O 0.638(2) -0.0142(9) 0.6547(8) 0.150(6) Uiso 1 1 d . . . . .
O2 O 0.449(3) -0.0029(10) 0.7390(9) 0.189(8) Uiso 1 1 d . . . . .
O3 O 0.7331(17) 0.2106(6) 0.5414(6) 0.095(4) Uiso 1 1 d . . . . .
O4 O 0.8573(17) 0.2882(6) 0.5863(5) 0.087(4) Uiso 1 1 d . . . . .
O5 O 0.3857(14) 0.3259(5) 0.7619(5) 0.069(3) Uiso 1 1 d . . . . .
O6 O 0.7181(14) 0.1611(5) 0.8390(5) 0.069(3) Uiso 1 1 d . . . . .
O7 O 0.4701(15) 0.3123(6) 1.1125(5) 0.071(3) Uiso 1 1 d . . . . .
O8 O 0.5836(13) 0.4061(5) 1.0678(4) 0.050(3) Uiso 1 1 d . . . . .
O9 O 0.1999(14) 0.4034(5) 1.0625(5) 0.057(3) Uiso 1 1 d . . . . .
O10 O -0.0418(15) 0.7346(6) 1.0465(5) 0.082(4) Uiso 1 1 d . . . . .
O11 O -0.0837(13) 0.7605(5) 1.1418(4) 0.051(3) Uiso 1 1 d . . . . .
O12 O 0.1898(13) 0.5960(5) 1.2727(4) 0.059(3) Uiso 1 1 d . . . . .
O13 O 0.2945(12) 0.4891(5) 1.2414(4) 0.046(3) Uiso 1 1 d . . . . .
N2 N 0.2849(15) 0.5075(6) 1.0244(5) 0.050(4) Uiso 1 1 d . . . . .
H2 H 0.332948 0.526839 0.993010 0.060 Uiso 1 1 calc R U . . .
C1 C 0.553(3) 0.0236(12) 0.6966(11) 0.108(8) Uiso 1 1 d . . . . .
C4 C 0.6977(13) 0.2000(6) 0.6419(4) 0.063(5) Uiso 1 1 d G . . . .
C5 C 0.6655(14) 0.2362(4) 0.6935(5) 0.061(5) Uiso 1 1 d G . . . .
H5 H 0.693178 0.282328 0.694074 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5921(14) 0.2035(6) 0.7441(4) 0.074(6) Uiso 1 1 d G . . . .
C7 C 0.5507(14) 0.1345(6) 0.7432(4) 0.092(6) Uiso 1 1 d G . . . .
H7 H 0.501565 0.112619 0.777074 0.110 Uiso 1 1 calc R U . . .
C2 C 0.5829(15) 0.0983(4) 0.6916(6) 0.085(6) Uiso 1 1 d G . . . .
C3 C 0.6563(15) 0.1311(6) 0.6409(4) 0.080(6) Uiso 1 1 d G . . . .
H3 H 0.677821 0.106889 0.606430 0.096 Uiso 1 1 calc R U . . .
C8 C 0.767(2) 0.2413(9) 0.5851(7) 0.063(5) Uiso 1 1 d . . . . .
C11 C 0.664(2) 0.2198(8) 0.9476(7) 0.064(5) Uiso 1 1 d . . . . .
H11 H 0.735546 0.179420 0.943807 0.076 Uiso 1 1 calc R U . . .
C12 C 0.626(2) 0.2510(8) 0.9994(7) 0.054(5) Uiso 1 1 d . . . . .
H12 H 0.666431 0.229033 1.031034 0.065 Uiso 1 1 calc R U . . .
C13 C 0.530(2) 0.3145(7) 1.0086(6) 0.047(4) Uiso 1 1 d . . . . .
C15 C 0.3434(19) 0.4053(7) 0.9666(6) 0.046(4) Uiso 1 1 d . . . . .
C16 C 0.2795(19) 0.4324(7) 0.9171(6) 0.042(4) Uiso 1 1 d . . . . .
H16 H 0.211838 0.473762 0.919744 0.050 Uiso 1 1 calc R U . . .
C18 C 0.3155(19) 0.3982(7) 0.8632(7) 0.053(5) Uiso 1 1 d . . . . .
H18 H 0.272285 0.417059 0.830880 0.063 Uiso 1 1 calc R U . . .
C21 C 0.4887(13) 0.3093(5) 0.9058(3) 0.044(4) Uiso 1 1 d G . . . .
C10 C 0.5948(13) 0.2488(5) 0.8990(3) 0.045(4) Uiso 1 1 d G . . . .
C9 C 0.6270(12) 0.2164(4) 0.8457(4) 0.048(4) Uiso 1 1 d G . . . .
N1 N 0.5531(12) 0.2444(4) 0.7992(3) 0.053(4) Uiso 1 1 d G . . . .
C20 C 0.4470(13) 0.3048(5) 0.8060(4) 0.048(4) Uiso 1 1 d G . . . .
C19 C 0.4147(13) 0.3373(4) 0.8593(4) 0.060(5) Uiso 1 1 d G . . . .
C22 C 0.4485(19) 0.3445(7) 0.9615(6) 0.043(4) Uiso 1 1 d . . . . .
C23 C 0.531(2) 0.3510(9) 1.0667(7) 0.057(5) Uiso 1 1 d . . . . .
C24 C 0.274(2) 0.4399(8) 1.0275(7) 0.049(4) Uiso 1 1 d . . . . .
C27 C 0.1846(12) 0.5723(4) 1.1752(3) 0.036(4) Uiso 1 1 d G . . . .
C26 C 0.2451(12) 0.5292(4) 1.1288(4) 0.044(4) Uiso 1 1 d G . . . .
H26 H 0.304614 0.487148 1.134990 0.052 Uiso 1 1 calc R U . . .
C25 C 0.2167(12) 0.5488(4) 1.0732(3) 0.054(5) Uiso 1 1 d G . . . .
C30 C 0.1278(12) 0.6116(4) 1.0640(3) 0.040(4) Uiso 1 1 d G . . . .
H30 H 0.108818 0.624744 1.026799 0.048 Uiso 1 1 calc R U . . .
C29 C 0.0673(12) 0.6547(4) 1.1103(4) 0.041(4) Uiso 1 1 d G . . . .
C28 C 0.0957(12) 0.6351(4) 1.1659(3) 0.044(4) Uiso 1 1 d G . . . .
H28 H 0.055207 0.663912 1.196928 0.053 Uiso 1 1 calc R U . . .
C31 C 0.225(2) 0.5501(8) 1.2372(6) 0.047(4) Uiso 1 1 d . . . . .
C32 C -0.027(2) 0.7219(8) 1.1020(7) 0.061(5) Uiso 1 1 d . . . . .
O14 O 0.6459(15) 0.5378(6) 0.6389(5) 0.084(4) Uiso 1 1 d . . . . .
N11 N 0.653(2) 0.4231(8) 0.6280(7) 0.089(5) Uiso 1 1 d . . . . .
H11A H 0.561000 0.381704 0.633305 0.107 Uiso 1 1 d R U . . .
C14 C 0.6170(19) 0.4859(8) 0.6119(6) 0.044(4) Uiso 1 1 d . . . . .
C17 C 0.5629(18) 0.4909(7) 0.5522(6) 0.037(4) Uiso 1 1 d . . . . .
C53 C 0.556(2) 0.4370(10) 0.5213(8) 0.089(6) Uiso 1 1 d . . . . .
H53 H 0.589121 0.393805 0.535883 0.107 Uiso 1 1 calc R U . . .
C54 C 0.503(3) 0.5596(11) 0.5366(9) 0.103(7) Uiso 1 1 d . . . . .
H54 H 0.500990 0.597872 0.560117 0.124 Uiso 1 1 calc R U . . .
O15 O 0.3069(16) 0.0050(6) 0.8383(5) 0.093(4) Uiso 1 1 d . . . . .
O16 O 0.3915(14) 0.1778(5) 1.1071(5) 0.072(3) Uiso 1 1 d . . . . .
O17 O 0.0093(12) 0.7006(5) 0.9367(4) 0.050(3) Uiso 1 1 d . . . . .
O18 O -0.2317(13) 0.6388(5) 0.7998(4) 0.052(3) Uiso 1 1 d . . . . .
O19 O 0.0540(18) 0.3237(7) 0.6621(6) 0.108(5) Uiso 1 1 d . . . . .
N3 N 0.3883(17) 0.5603(6) 0.8181(5) 0.060(4) Uiso 1 1 d . . . . .
H3A H 0.407604 0.569708 0.852258 0.072 Uiso 1 1 calc R U . . .
H3B H 0.466202 0.537785 0.794699 0.072 Uiso 1 1 calc R U . . .
N4 N 0.1170(17) 0.6150(6) 0.8369(5) 0.062(4) Uiso 1 1 d . . . . .
H4A H 0.132120 0.625238 0.871277 0.074 Uiso 1 1 calc R U . . .
H4B H 0.021233 0.627230 0.824753 0.074 Uiso 1 1 calc R U . . .
N5 N 0.0662(17) 0.4555(7) 0.5645(6) 0.075(4) Uiso 1 1 d . . . . .
H5A H 0.023512 0.445695 0.534015 0.090 Uiso 1 1 calc R U . . .
H5B H 0.105015 0.422641 0.585404 0.090 Uiso 1 1 calc R U . . .
N6 N 0.0201(15) 0.5676(6) 0.5516(5) 0.050(4) Uiso 1 1 d . . . . .
H6A H -0.024014 0.561393 0.520703 0.060 Uiso 1 1 calc R U . . .
H6B H 0.027698 0.608985 0.563443 0.060 Uiso 1 1 calc R U . . .
C33 C 0.072(2) 0.5180(10) 0.5784(8) 0.074(5) Uiso 1 1 d . . . . .
C35 C 0.2054(13) 0.4835(4) 0.6683(4) 0.054(5) Uiso 1 1 d G . . . .
H35 H 0.238549 0.439910 0.652885 0.065 Uiso 1 1 calc R U . . .
C34 C 0.1142(14) 0.5319(5) 0.6378(3) 0.055(5) Uiso 1 1 d G . . . .
C39 C 0.0647(13) 0.5970(5) 0.6608(4) 0.063(5) Uiso 1 1 d G . . . .
H39 H 0.003642 0.629342 0.640433 0.075 Uiso 1 1 calc R U . . .
C38 C 0.1063(13) 0.6137(4) 0.7144(4) 0.051(4) Uiso 1 1 d G . . . .
H38 H 0.073186 0.657257 0.729803 0.062 Uiso 1 1 calc R U . . .
C37 C 0.1975(14) 0.5653(5) 0.7449(3) 0.058(5) Uiso 1 1 d G . . . .
C36 C 0.2471(13) 0.5002(5) 0.7218(4) 0.060(5) Uiso 1 1 d G . . . .
H36 H 0.308094 0.467826 0.742256 0.072 Uiso 1 1 calc R U . . .
C40 C 0.243(2) 0.5798(8) 0.8020(6) 0.050(4) Uiso 1 1 d . . . . .
N7 N 0.311(2) 0.0328(10) 0.4636(8) 0.141(7) Uiso 1 1 d . . . . .
H7A H 0.330785 0.023049 0.427349 0.169 Uiso 1 1 calc R U . . .
H7B H 0.293802 0.000143 0.489124 0.169 Uiso 1 1 calc R U . . .
N8 N 0.327(3) 0.1624(11) 0.4556(9) 0.165(9) Uiso 1 1 d . . . . .
H8A H 0.348766 0.165848 0.418501 0.198 Uiso 1 1 calc R U . . .
H8B H 0.319123 0.199052 0.476314 0.198 Uiso 1 1 calc R U . . .
N9 N 0.009(3) 0.0886(11) 0.7563(11) 0.169(9) Uiso 1 1 d . . . . .
H9A H -0.029825 0.092492 0.796734 0.203 Uiso 1 1 d R U . . .
H9B H -0.091898 0.076618 0.743662 0.203 Uiso 1 1 d R U . . .
N10 N 0.088(2) 0.2080(8) 0.7444(7) 0.098(5) Uiso 1 1 d . . . . .
H10A H 0.048582 0.225568 0.777597 0.118 Uiso 1 1 calc R U . . .
H10B H 0.140517 0.233351 0.717342 0.118 Uiso 1 1 calc R U . . .
C41 C 0.069(3) 0.1447(13) 0.7354(10) 0.114(8) Uiso 1 1 d . . . . .
C46 C 0.3062(15) 0.1619(7) 0.5753(6) 0.136(9) Uiso 1 1 d G . . . .
H46 H 0.390227 0.189151 0.555387 0.163 Uiso 1 1 calc R U . . .
C47 C 0.2515(17) 0.1716(5) 0.6341(6) 0.084(6) Uiso 1 1 d G . . . .
H47 H 0.298884 0.205361 0.653569 0.101 Uiso 1 1 calc R U . . .
C42 C 0.1259(17) 0.1308(7) 0.6639(4) 0.078(6) Uiso 1 1 d G . . . .
C43 C 0.0550(15) 0.0804(6) 0.6348(6) 0.123(8) Uiso 1 1 d G . . . .
H43 H -0.029070 0.053088 0.654741 0.148 Uiso 1 1 calc R U . . .
C44 C 0.1097(17) 0.0706(6) 0.5760(6) 0.090(6) Uiso 1 1 d G . . . .
H44 H 0.062273 0.036877 0.556558 0.108 Uiso 1 1 calc R U . . .
C45 C 0.2353(18) 0.1114(7) 0.5462(4) 0.089(6) Uiso 1 1 d G . . . .
C48 C 0.308(3) 0.1013(14) 0.4808(10) 0.122(8) Uiso 1 1 d . . . . .
N12 N 0.2827(16) 0.1246(6) 0.9080(5) 0.057(4) Uiso 1 1 d . . . . .
H12A H 0.219705 0.158675 0.896568 0.068 Uiso 1 1 calc R U . . .
H12B H 0.323340 0.092003 0.884531 0.068 Uiso 1 1 calc R U . . .
N13 N 0.2582(16) 0.1706(6) 0.9987(5) 0.064(4) Uiso 1 1 d . . . . .
H13A H 0.194764 0.205481 0.988857 0.077 Uiso 1 1 calc R U . . .
H13B H 0.283227 0.167405 1.033321 0.077 Uiso 1 1 calc R U . . .
C49 C 0.317(2) 0.1225(8) 0.9611(7) 0.060(5) Uiso 1 1 d . . . . .
C50 C 0.409(2) 0.0587(8) 0.9808(7) 0.053(5) Uiso 1 1 d . . . . .
C51 C 0.535(2) 0.0272(9) 0.9471(8) 0.067(5) Uiso 1 1 d . . . . .
H51 H 0.563376 0.044580 0.909604 0.080 Uiso 1 1 calc R U . . .
C52 C 0.371(2) 0.0312(9) 1.0360(8) 0.068(5) Uiso 1 1 d . . . . .
H52 H 0.282418 0.051782 1.062034 0.081 Uiso 1 1 calc R U . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.31(2) . ?
O2 C1 1.30(3) . ?
O3 C8 1.263(17) . ?
O4 C8 1.187(18) . ?
O5 C20 1.250(11) . ?
O6 C9 1.247(11) . ?
O7 C23 1.332(18) . ?
O8 C23 1.168(16) . ?
O9 C24 1.176(17) . ?
O10 C32 1.334(18) . ?
O11 C32 1.220(16) . ?
O12 C31 1.220(14) . ?
O13 C31 1.276(15) . ?
N2 H2 0.8600 . ?
N2 C24 1.311(16) . ?
N2 C25 1.425(12) . ?
C1 C2 1.48(2) . ?
C4 C5 1.3900 . ?
C4 C3 1.3900 . ?
C4 C8 1.571(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C6 N1 1.508(9) . ?
C7 H7 0.9300 . ?
C7 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.348(18) . ?
C11 C10 1.421(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.404(18) . ?
C13 C22 1.445(18) . ?
C13 C23 1.546(19) . ?
C15 C16 1.405(18) . ?
C15 C22 1.390(17) . ?
C15 C24 1.593(19) . ?
C16 H16 0.9300 . ?
C16 C18 1.418(17) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(15) . ?
C21 C10 1.3900 . ?
C21 C19 1.3900 . ?
C21 C22 1.465(14) . ?
C10 C9 1.3900 . ?
C9 N1 1.3900 . ?
N1 C20 1.3900 . ?
C20 C19 1.3900 . ?
C27 C26 1.3900 . ?
C27 C28 1.3900 . ?
C27 C31 1.573(16) . ?
C26 H26 0.9300 . ?
C26 C25 1.3900 . ?
C25 C30 1.3900 . ?
C30 H30 0.9300 . ?
C30 C29 1.3900 . ?
C29 C28 1.3900 . ?
C29 C32 1.479(17) . ?
C28 H28 0.9300 . ?
O14 C14 1.246(15) . ?
N11 H11A 1.1038 . ?
N11 C14 1.288(18) . ?
C14 C17 1.517(18) . ?
C17 C53 1.289(18) . ?
C17 C54 1.44(2) . ?
C53 H53 0.9300 . ?
C53 C54 1.49(2) 2_666 ?
C54 H54 0.9300 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C40 1.287(16) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C40 1.341(16) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C33 1.264(18) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C33 1.214(19) . ?
C33 C34 1.508(18) . ?
C35 H35 0.9300 . ?
C35 C34 1.3900 . ?
C35 C36 1.3900 . ?
C34 C39 1.3900 . ?
C39 H39 0.9300 . ?
C39 C38 1.3900 . ?
C38 H38 0.9300 . ?
C38 C37 1.3900 . ?
C37 C36 1.3900 . ?
C37 C40 1.470(15) . ?
C36 H36 0.9300 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C48 1.39(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N8 C48 1.31(3) . ?
N9 H9A 0.9502 . ?
N9 H9B 0.9314 . ?
N9 C41 1.26(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C41 1.27(2) . ?
C41 C42 1.69(2) . ?
C46 H46 0.9300 . ?
C46 C47 1.3900 . ?
C46 C45 1.3900 . ?
C47 H47 0.9300 . ?
C47 C42 1.3900 . ?
C42 C43 1.3900 . ?
C43 H43 0.9300 . ?
C43 C44 1.3900 . ?
C44 H44 0.9300 . ?
C44 C45 1.3900 . ?
C45 C48 1.56(2) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N12 C49 1.305(17) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N13 C49 1.310(16) . ?
C49 C50 1.49(2) . ?
C50 C51 1.293(19) . ?
C50 C52 1.38(2) . ?
C51 H51 0.9300 . ?
C51 C52 1.39(2) 2_657 ?
C52 H52 0.9300 . ?

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
C24 N2 H2 120.0 . . ?
C24 N2 C25 119.9(13) . . ?
C25 N2 H2 120.0 . . ?
O1 C1 C2 115(2) . . ?
O2 C1 O1 122(2) . . ?
O2 C1 C2 123(2) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C8 117.7(10) . . ?
C3 C4 C8 122.1(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 N1 119.1(9) . . ?
C7 C6 N1 120.9(9) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 C6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C7 C2 C1 115.6(14) . . ?
C7 C2 C3 120.0 . . ?
C3 C2 C1 124.0(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
O3 C8 C4 109.8(15) . . ?
O4 C8 O3 128.2(19) . . ?
O4 C8 C4 121.2(15) . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(15) . . ?
C10 C11 H11 120.1 . . ?
C11 C12 H12 117.9 . . ?
C11 C12 C13 124.3(16) . . ?
C13 C12 H12 117.9 . . ?
C12 C13 C22 118.1(13) . . ?
C12 C13 C23 117.7(14) . . ?
C22 C13 C23 124.0(13) . . ?
C16 C15 C24 118.7(13) . . ?
C22 C15 C16 118.5(13) . . ?
C22 C15 C24 122.4(13) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C18 121.7(14) . . ?
C18 C16 H16 119.2 . . ?
C16 C18 H18 120.4 . . ?
C19 C18 C16 119.2(14) . . ?
C19 C18 H18 120.4 . . ?
C10 C21 C19 120.0 . . ?
C10 C21 C22 121.8(9) . . ?
C19 C21 C22 118.2(9) . . ?
C21 C10 C11 119.0(9) . . ?
C9 C10 C11 120.9(9) . . ?
C9 C10 C21 120.0 . . ?
O6 C9 C10 121.1(9) . . ?
O6 C9 N1 118.9(9) . . ?
C10 C9 N1 120.0 . . ?
C9 N1 C6 115.4(8) . . ?
C9 N1 C20 120.0 . . ?
C20 N1 C6 124.6(8) . . ?
O5 C20 N1 115.5(9) . . ?
O5 C20 C19 124.5(9) . . ?
C19 C20 N1 120.0 . . ?
C18 C19 C21 122.1(9) . . ?
C18 C19 C20 117.8(9) . . ?
C20 C19 C21 120.0 . . ?
C13 C22 C21 116.6(12) . . ?
C15 C22 C13 123.1(13) . . ?
C15 C22 C21 120.3(13) . . ?
O7 C23 C13 112.8(14) . . ?
O8 C23 O7 126.2(15) . . ?
O8 C23 C13 121.0(16) . . ?
O9 C24 N2 132.0(15) . . ?
O9 C24 C15 115.4(13) . . ?
N2 C24 C15 111.2(14) . . ?
C26 C27 C28 120.0 . . ?
C26 C27 C31 118.9(8) . . ?
C28 C27 C31 121.1(8) . . ?
C27 C26 H26 120.0 . . ?
C27 C26 C25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C25 N2 121.3(8) . . ?
C26 C25 C30 120.0 . . ?
C30 C25 N2 118.6(8) . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C29 C32 121.4(9) . . ?
C28 C29 C30 120.0 . . ?
C28 C29 C32 118.6(9) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
O12 C31 O13 131.0(14) . . ?
O12 C31 C27 113.4(12) . . ?
O13 C31 C27 115.5(12) . . ?
O10 C32 C29 112.1(13) . . ?
O11 C32 O10 125.0(16) . . ?
O11 C32 C29 123.0(15) . . ?
C14 N11 H11A 124.3 . . ?
O14 C14 N11 123.2(15) . . ?
O14 C14 C17 122.8(14) . . ?
N11 C14 C17 113.2(14) . . ?
C53 C17 C14 122.4(15) . . ?
C53 C17 C54 123.7(15) . . ?
C54 C17 C14 113.6(14) . . ?
C17 C53 H53 118.4 . . ?
C17 C53 C54 123.3(18) . 2_666 ?
C54 C53 H53 118.4 2_666 . ?
C17 C54 C53 112.9(16) . 2_666 ?
C17 C54 H54 123.6 . . ?
C53 C54 H54 123.6 2_666 . ?
H3A N3 H3B 120.0 . . ?
C40 N3 H3A 120.0 . . ?
C40 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C40 N4 H4A 120.0 . . ?
C40 N4 H4B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C33 N5 H5A 120.0 . . ?
C33 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C33 N6 H6A 120.0 . . ?
C33 N6 H6B 120.0 . . ?
N5 C33 C34 117.7(17) . . ?
N6 C33 N5 124.6(17) . . ?
N6 C33 C34 116.7(15) . . ?
C34 C35 H35 120.0 . . ?
C34 C35 C36 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C34 C33 122.6(10) . . ?
C35 C34 C39 120.0 . . ?
C39 C34 C33 117.4(10) . . ?
C34 C39 H39 120.0 . . ?
C38 C39 C34 120.0 . . ?
C38 C39 H39 120.0 . . ?
C39 C38 H38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 C40 122.3(9) . . ?
C36 C37 C40 117.7(9) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
N3 C40 N4 122.4(14) . . ?
N3 C40 C37 123.8(14) . . ?
N4 C40 C37 113.8(13) . . ?
H7A N7 H7B 120.0 . . ?
C48 N7 H7A 120.0 . . ?
C48 N7 H7B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C48 N8 H8A 120.0 . . ?
C48 N8 H8B 120.0 . . ?
H9A N9 H9B 100.3 . . ?
C41 N9 H9A 110.9 . . ?
C41 N9 H9B 115.2 . . ?
H10A N10 H10B 120.0 . . ?
C41 N10 H10A 120.0 . . ?
C41 N10 H10B 120.0 . . ?
N9 C41 N10 146(3) . . ?
N9 C41 C42 105(2) . . ?
N10 C41 C42 108(2) . . ?
C47 C46 H46 120.0 . . ?
C47 C46 C45 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 H47 120.0 . . ?
C42 C47 C46 120.0 . . ?
C42 C47 H47 120.0 . . ?
C47 C42 C41 117.3(13) . . ?
C47 C42 C43 120.0 . . ?
C43 C42 C41 122.7(13) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 C42 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C43 C44 C45 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C48 117.3(14) . . ?
C44 C45 C46 120.0 . . ?
C44 C45 C48 122.6(14) . . ?
N7 C48 C45 113(2) . . ?
N8 C48 N7 137(2) . . ?
N8 C48 C45 109(2) . . ?
H12A N12 H12B 120.0 . . ?
C49 N12 H12A 120.0 . . ?
C49 N12 H12B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C49 N13 H13A 120.0 . . ?
C49 N13 H13B 120.0 . . ?
N12 C49 N13 122.7(15) . . ?
N12 C49 C50 117.9(14) . . ?
N13 C49 C50 119.1(15) . . ?
C51 C50 C49 121.2(17) . . ?
C51 C50 C52 116.2(16) . . ?
C52 C50 C49 122.5(16) . . ?
C50 C51 H51 118.3 . . ?
C50 C51 C52 123.4(17) . 2_657 ?
C52 C51 H51 118.3 2_657 . ?
C50 C52 C51 120.4(17) . 2_657 ?
C50 C52 H52 119.8 . . ?
C51 C52 H52 119.8 2_657 . ?

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 C1 C2 C7 -156.8(15) . . . . ?
O1 C1 C2 C3 16(3) . . . . ?
O2 C1 C2 C7 24(3) . . . . ?
O2 C1 C2 C3 -162.9(18) . . . . ?
O5 C20 C19 C18 -3.1(13) . . . . ?
O5 C20 C19 C21 179.7(12) . . . . ?
O6 C9 N1 C6 0.2(11) . . . . ?
O6 C9 N1 C20 178.2(11) . . . . ?
N2 C25 C30 C29 -176.8(10) . . . . ?
C1 C2 C3 C4 -172.7(15) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 N1 -178.1(10) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C8 O3 -157.2(11) . . . . ?
C5 C4 C8 O4 32(2) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C5 C6 N1 C9 -124.5(7) . . . . ?
C5 C6 N1 C20 57.7(10) . . . . ?
C6 C7 C2 C1 173.2(14) . . . . ?
C6 C7 C2 C3 0.0 . . . . ?
C6 N1 C20 O5 -1.9(12) . . . . ?
C6 N1 C20 C19 177.8(10) . . . . ?
C7 C6 N1 C9 57.5(9) . . . . ?
C7 C6 N1 C20 -120.4(8) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C8 O3 18.0(17) . . . . ?
C3 C4 C8 O4 -152.7(13) . . . . ?
C8 C4 C5 C6 175.2(11) . . . . ?
C8 C4 C3 C2 -175.0(12) . . . . ?
C11 C12 C13 C22 8(2) . . . . ?
C11 C12 C13 C23 -167.1(16) . . . . ?
C11 C10 C9 O6 -0.3(13) . . . . ?
C11 C10 C9 N1 177.8(12) . . . . ?
C12 C11 C10 C21 0(2) . . . . ?
C12 C11 C10 C9 -177.7(12) . . . . ?
C12 C13 C22 C15 176.8(15) . . . . ?
C12 C13 C22 C21 -6(2) . . . . ?
C12 C13 C23 O7 -60(2) . . . . ?
C12 C13 C23 O8 118.9(18) . . . . ?
C15 C16 C18 C19 0(2) . . . . ?
C16 C15 C22 C13 176.1(15) . . . . ?
C16 C15 C22 C21 -1(2) . . . . ?
C16 C15 C24 O9 117.6(17) . . . . ?
C16 C15 C24 N2 -50.5(19) . . . . ?
C16 C18 C19 C21 -3.2(18) . . . . ?
C16 C18 C19 C20 179.6(11) . . . . ?
C21 C10 C9 O6 -178.1(12) . . . . ?
C21 C10 C9 N1 0.0 . . . . ?
C10 C11 C12 C13 -5(3) . . . . ?
C10 C21 C19 C18 -177.1(12) . . . . ?
C10 C21 C19 C20 0.0 . . . . ?
C10 C21 C22 C13 2.1(17) . . . . ?
C10 C21 C22 C15 179.3(11) . . . . ?
C10 C9 N1 C6 -178.0(9) . . . . ?
C10 C9 N1 C20 0.0 . . . . ?
C9 N1 C20 O5 -179.7(11) . . . . ?
C9 N1 C20 C19 0.0 . . . . ?
N1 C6 C7 C2 178.0(10) . . . . ?
N1 C20 C19 C18 177.2(12) . . . . ?
N1 C20 C19 C21 0.0 . . . . ?
C19 C21 C10 C11 -177.8(12) . . . . ?
C19 C21 C10 C9 0.0 . . . . ?
C19 C21 C22 C13 -179.1(11) . . . . ?
C19 C21 C22 C15 -1.9(17) . . . . ?
C22 C13 C23 O7 126.1(16) . . . . ?
C22 C13 C23 O8 -56(2) . . . . ?
C22 C15 C16 C18 2(2) . . . . ?
C22 C15 C24 O9 -55(2) . . . . ?
C22 C15 C24 N2 137.3(15) . . . . ?
C22 C21 C10 C11 0.9(14) . . . . ?
C22 C21 C10 C9 178.8(11) . . . . ?
C22 C21 C19 C18 4.1(13) . . . . ?
C22 C21 C19 C20 -178.8(11) . . . . ?
C23 C13 C22 C15 -9(2) . . . . ?
C23 C13 C22 C21 168.3(14) . . . . ?
C24 N2 C25 C26 44.1(15) . . . . ?
C24 N2 C25 C30 -139.2(11) . . . . ?
C24 C15 C16 C18 -170.7(14) . . . . ?
C24 C15 C22 C13 -12(2) . . . . ?
C24 C15 C22 C21 171.4(13) . . . . ?
C27 C26 C25 N2 176.7(10) . . . . ?
C27 C26 C25 C30 0.0 . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C26 C27 C31 O12 169.3(10) . . . . ?
C26 C27 C31 O13 -7.9(16) . . . . ?
C26 C25 C30 C29 0.0 . . . . ?
C25 N2 C24 O9 10(3) . . . . ?
C25 N2 C24 C15 175.0(10) . . . . ?
C25 C30 C29 C28 0.0 . . . . ?
C25 C30 C29 C32 179.8(11) . . . . ?
C30 C29 C28 C27 0.0 . . . . ?
C30 C29 C32 O10 -1.1(18) . . . . ?
C30 C29 C32 O11 179.1(12) . . . . ?
C28 C27 C26 C25 0.0 . . . . ?
C28 C27 C31 O12 -8.4(17) . . . . ?
C28 C27 C31 O13 174.5(10) . . . . ?
C28 C29 C32 O10 178.7(10) . . . . ?
C28 C29 C32 O11 -1(2) . . . . ?
C31 C27 C26 C25 -177.7(10) . . . . ?
C31 C27 C28 C29 177.6(10) . . . . ?
C32 C29 C28 C27 -179.8(11) . . . . ?
O14 C14 C17 C53 170.4(17) . . . . ?
O14 C14 C17 C54 -16(2) . . . . ?
N11 C14 C17 C53 0(2) . . . . ?
N11 C14 C17 C54 173.2(16) . . . . ?
C14 C17 C53 C54 177.8(16) . . . 2_666 ?
C14 C17 C54 C53 -177.9(14) . . . 2_666 ?
C53 C17 C54 C53 -4(3) . . . 2_666 ?
C54 C17 C53 C54 5(3) . . . 2_666 ?
N5 C33 C34 C35 24(2) . . . . ?
N5 C33 C34 C39 -158.7(13) . . . . ?
N6 C33 C34 C35 -167.0(13) . . . . ?
N6 C33 C34 C39 10(2) . . . . ?
C33 C34 C39 C38 -177.4(12) . . . . ?
C35 C34 C39 C38 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C34 C39 C38 C37 0.0 . . . . ?
C39 C38 C37 C36 0.0 . . . . ?
C39 C38 C37 C40 -179.1(12) . . . . ?
C38 C37 C36 C35 0.0 . . . . ?
C38 C37 C40 N3 -140.6(13) . . . . ?
C38 C37 C40 N4 40.1(17) . . . . ?
C36 C35 C34 C33 177.3(13) . . . . ?
C36 C35 C34 C39 0.0 . . . . ?
C36 C37 C40 N3 40.3(19) . . . . ?
C36 C37 C40 N4 -139.0(11) . . . . ?
C40 C37 C36 C35 179.1(12) . . . . ?
N9 C41 C42 C47 -156.0(17) . . . . ?
N9 C41 C42 C43 23(2) . . . . ?
N10 C41 C42 C47 30(2) . . . . ?
N10 C41 C42 C43 -151.1(14) . . . . ?
C41 C42 C43 C44 -178.9(13) . . . . ?
C46 C47 C42 C41 178.9(13) . . . . ?
C46 C47 C42 C43 0.0 . . . . ?
C46 C45 C48 N7 145.7(15) . . . . ?
C46 C45 C48 N8 -42(2) . . . . ?
C47 C46 C45 C44 0.0 . . . . ?
C47 C46 C45 C48 -177.7(14) . . . . ?
C47 C42 C43 C44 0.0 . . . . ?
C42 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C43 C44 C45 C48 177.6(15) . . . . ?
C44 C45 C48 N7 -32(2) . . . . ?
C44 C45 C48 N8 139.9(17) . . . . ?
C45 C46 C47 C42 0.0 . . . . ?
N12 C49 C50 C51 40(2) . . . . ?
N12 C49 C50 C52 -142.1(16) . . . . ?
N13 C49 C50 C51 -146.4(16) . . . . ?
N13 C49 C50 C52 31(2) . . . . ?
C49 C50 C51 C52 178.0(15) . . . 2_657 ?
C49 C50 C52 C51 -177.9(15) . . . 2_657 ?
C51 C50 C52 C51 0(3) . . . 2_657 ?
C52 C50 C51 C52 0(3) . . . 2_657 ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 335 electrons were 
found in a volume of 992Å³ in 1 void per unit cell. 
This is consistent with the presence of 
17[H2O] per Unit Cell 
which account for 340 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.898 0.000 0.000 992.4 335.3 '34 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ov_hofs2_auto
_database_code_depnum_ccdc_archive 'CCDC 2303291'
loop_
_audit_author_name
_audit_author_address
'Neil Champness'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
_chemical_name_common            ?
_chemical_name_systematic        HOF_2
_chemical_formula_moiety         'C15 H5 N O6, C8 H12 N4, C4 H4 N O, 4(H2 O)'
_chemical_formula_sum            'C27 H29 N6 O11'
_chemical_formula_weight         613.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   7.13610(10)
_cell_length_b                   9.06550(10)
_cell_length_c                   20.9919(3)
_cell_angle_alpha                88.4100(10)
_cell_angle_beta                 87.4730(10)
_cell_angle_gamma                83.4320(10)
_cell_volume                     1347.44(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    39448
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      78.8720
_cell_measurement_theta_min      4.1590
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_preparation       'see experimental'
_exptl_crystal_recrystallization_method 'see experimental'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            56339
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.085
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  23.00   0.50    2.00    --  -49.01  88.00-160.00  198
  2  ω    -21.00  76.00   0.50    2.00    --   49.01 -88.00  82.00  194
  3  ω   -117.00 -18.00   0.50   10.00    --  -90.00  88.00-160.00  198
  4  ω   -161.00 -79.00   0.50   10.00    --  -90.00 -88.00  82.00  164
  5  ω    101.00 178.00   0.50   10.00    --  111.50  88.00-160.00  154
  6  ω     40.00 138.00   0.50   10.00    --  111.50 -88.00  82.00  196
  7  ω   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00   0.00   52
  8  ω   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00 150.00   52
  9  ω   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  60.00   52
 10  ω    -34.00  25.00   0.50    2.00    --  -49.01  19.00 120.00  118
 11  ω   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  30.00   52
 12  ω    -24.00  26.00   0.50    2.00    --   49.01 -19.00   0.00  100
 13  ω    -24.00  26.00   0.50    2.00    --   49.01 -19.00 150.00  100
 14  ω     94.00 121.00   0.50    2.00    --   49.01  57.00-150.00   54
 15  ω    -55.00 -18.00   0.50   10.00    --  -90.00  45.00-150.00   74
 16  ω    -75.00 -18.00   0.50   10.00    --  -90.00  61.00 150.00  114
 17  ω   -161.00-105.00   0.50   10.00    --  -90.00 -77.00 150.00  112
 18  ω   -161.00-105.00   0.50   10.00    --  -90.00 -77.00-180.00  112
 19  ω    -75.00 -18.00   0.50   10.00    --  -90.00  61.00 -30.00  114
 20  ω    101.00 178.00   0.50   10.00    --  111.50  30.00 -60.00  154
 21  ω     40.00 105.00   0.50   10.00    --  111.50 -95.00  60.00  130
 22  ω     40.00 108.00   0.50   10.00    --  111.50-110.00 -48.66  136
 23  ω     40.00 105.00   0.50   10.00    --  111.50 -95.00  30.00  130
 24  ω    101.00 178.00   0.50   10.00    --  111.50  15.00  30.00  154
 25  ω     95.00 178.00   0.50   10.00    --  111.50 125.00 -30.00  166
 26  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00   0.00   54
 27  ω     40.00 111.00   0.50   10.00    --  111.50-125.00 -30.00  142
 28  ω     40.00 111.00   0.50   10.00    --  111.50-125.00  30.00  142
 29  ω     40.00 105.00   0.50   10.00    --  111.50 -95.00-150.00  130
 30  ω     40.00  97.00   0.50   10.00    --  111.50 -77.00 120.00  114
 31  ω    101.00 178.00   0.50   10.00    --  111.50  45.00  90.00  154
 32  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00-180.00   54
 33  ω     98.00 178.00   0.50   10.00    --  111.50  61.00-120.00  160
 34  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00 -60.00   54
 35  ω     40.00 105.00   0.50   10.00    --  111.50 -95.00-120.00  130
 36  ω     40.00 109.00   0.50   10.00    --  111.50-117.00  35.61  138
 37  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00 120.00   54
 38  ω    101.00 178.00   0.50   10.00    --  111.50  45.00 150.00  154
 39  ω     40.00 108.00   0.50   10.00    --  111.50-109.00-168.57  136
 40  ω    101.00 178.00   0.50   10.00    --  111.50  30.00-150.00  154
 41  ω     40.00  97.00   0.50   10.00    --  111.50 -77.00  60.00  114
 42  ω    101.00 178.00   0.50   10.00    --  111.50  15.00-120.00  154
 43  ω     40.00 111.00   0.50   10.00    --  111.50-125.00 -60.00  142
 44  ω     40.00 111.00   0.50   10.00    --  111.50-125.00   0.00  142
 45  ω     40.00 105.00   0.50   10.00    --  111.50 -95.00  90.00  130
 46  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00  90.00   54
 47  ω     40.00  67.00   0.50   10.00    --  111.50 -61.00-120.00   54
 48  ω   -120.00 -37.00   0.50    2.00    --  -49.01 -51.00 -40.03  166
 49  ω   -120.00 -38.00   0.50    2.00    --  -49.01 -45.00  59.20  164
 50  ω   -120.00 -37.00   0.50    2.00    --  -49.01 -50.00 114.71  166
 51  ω   -121.00 -39.00   0.50    2.00    --  -49.01 -38.00   0.00  164
 52  ω   -120.00 -94.00   0.50    2.00    --  -49.01 -57.00  90.00   52
 53  ω   -120.00 -37.00   0.50    2.00    --  -49.01 -49.00 167.14  166
 54  ω   -121.00 -39.00   0.50    2.00    --  -49.01 -38.00-150.00  164
 55  ω     37.00 121.00   0.50    2.00    --   49.01  52.00 -54.38  168
 56  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00 -48.31  166
 57  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00-158.42  166
 58  ω   -161.00 -80.00   0.50   10.00    --  -90.00 -52.00  -4.89  162
 59  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00  13.54  166
 60  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 -28.63  166
 61  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00-148.89  166
 62  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -49.00  58.47  166
 63  ω   -161.00 -85.00   0.50   10.00    --  -90.00 -53.00-171.35  152
 64  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00  86.42  166
 65  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00 -89.69  166
 66  ω   -161.00 -79.00   0.50   10.00    --  -90.00 -45.00 150.00  164
 67  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00  45.32  166
 68  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 106.62  166
 69  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00 127.79  166
 70  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -50.00-121.67  166
 71  ω   -161.00 -78.00   0.50   10.00    --  -90.00 -51.00 -62.02  166
 72  ω     98.00 178.00   0.50   10.00    --  111.50  61.00  60.00  160
 73  ω    101.00 178.00   0.50   10.00    --  111.50  45.00-150.00  154
 74  ω     98.00 178.00   0.50   10.00    --  111.50  61.00 -30.00  160
 75  ω     98.00 178.00   0.50   10.00    --  111.50  61.00 150.00  160
 76  ω    101.00 178.00   0.50   10.00    --  111.50  45.00 120.00  154
 77  ω    105.00 178.00   0.50   10.00    --  111.50  77.00 -90.00  146
 78  ω     98.00 178.00   0.50   10.00    --  111.50  61.00   0.00  160
 79  ω     97.00 178.00   0.50   10.00    --  111.50  60.00  40.10  162
 80  ω    101.00 178.00   0.50   10.00    --  111.50  30.00 -30.00  154
 81  ω     98.00 151.00   0.50   10.00    --  111.50  61.00-150.00  106
 82  ω    101.00 178.00   0.50   10.00    --  111.50  45.00  30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5421
_reflns_number_total             5728
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+1.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          
'Non-hydrogen atoms were refined anisotropically. All hydrogen atoms were geometrically placed and refined using a riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O9-H9A = O9-H9B
 0.87 with sigma of 0.02
 O10-H10A = O10-H10B
 0.87 with sigma of 0.02
 O8-H8A
 0.87 with sigma of 0.02
 O11-H11A = O11-H11B
 0.87 with sigma of 0.02
 H9A-H9B
 1.38 with sigma of 0.04
 H10A-H10B
 1.38 with sigma of 0.04
 H11A-H11B
 1.38 with sigma of 0.04
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C12(H12), C13(H13), C18(H18), C19(H19), C21(H21),
 C22(H22), C26(H26), C27(H27)
3.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B)
;
_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
C1 C 0.7113(2) 0.35893(15) 0.14075(7) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.91410(19) -0.15276(15) 0.23122(6) 0.0150(3) Uani 1 1 d . . . . .
C3 C 0.72937(19) 0.25003(15) 0.19679(6) 0.0152(3) Uani 1 1 d . . . . .
C4 C 0.80054(19) 0.10128(15) 0.18871(6) 0.0146(3) Uani 1 1 d . . . . .
H4 H 0.837605 0.066884 0.147201 0.018 Uiso 1 1 calc R U . . .
C5 C 0.81777(19) 0.00286(15) 0.24084(6) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.75889(19) 0.05222(15) 0.30198(6) 0.0151(3) Uani 1 1 d . . . . .
H6 H 0.766237 -0.014691 0.337660 0.018 Uiso 1 1 calc R U . . .
C7 C 0.68971(19) 0.20036(15) 0.30957(6) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.67702(19) 0.29887(15) 0.25781(7) 0.0161(3) Uani 1 1 d . . . . .
H8 H 0.632233 0.400384 0.264142 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7638(2) 0.27231(15) 0.41697(6) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.4412(2) 0.32880(15) 0.37669(6) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.38970(19) 0.43140(15) 0.42963(6) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.2129(2) 0.51089(15) 0.43336(6) 0.0163(3) Uani 1 1 d . . . . .
H12 H 0.123225 0.497621 0.402470 0.020 Uiso 1 1 calc R U . . .
C13 C 0.16537(19) 0.61124(15) 0.48271(7) 0.0162(3) Uani 1 1 d . . . . .
H13 H 0.044121 0.666815 0.484702 0.019 Uiso 1 1 calc R U . . .
C14 C 0.29338(19) 0.62991(15) 0.52840(6) 0.0147(3) Uani 1 1 d . . . . .
C15 C 0.47536(19) 0.54997(14) 0.52490(6) 0.0139(3) Uani 1 1 d . . . . .
N1 N 0.62845(16) 0.26146(13) 0.37146(5) 0.0150(2) Uani 1 1 d . . . . .
O1 O 0.62433(17) 0.48463(11) 0.15127(5) 0.0248(2) Uani 1 1 d . . . . .
O2 O 0.78294(15) 0.31742(11) 0.08765(5) 0.0206(2) Uani 1 1 d . . . . .
O3 O 0.93628(15) -0.20055(11) 0.17574(5) 0.0206(2) Uani 1 1 d . . . . .
O4 O 0.97329(14) -0.22517(10) 0.28050(5) 0.0173(2) Uani 1 1 d . . . . .
O5 O 0.92125(14) 0.20531(12) 0.41093(5) 0.0210(2) Uani 1 1 d . . . . .
O6 O 0.32892(15) 0.30447(12) 0.33763(5) 0.0209(2) Uani 1 1 d . . . . .
C16 C 0.44349(19) 0.81635(15) 0.15804(7) 0.0164(3) Uani 1 1 d . . . . .
C17 C 0.36859(19) 0.97533(15) 0.16242(7) 0.0153(3) Uani 1 1 d . . . . .
C18 C 0.3929(2) 1.07376(15) 0.11116(7) 0.0166(3) Uani 1 1 d . . . . .
H18 H 0.454470 1.038223 0.072601 0.020 Uiso 1 1 calc R U . . .
C19 C 0.3276(2) 1.22321(15) 0.11632(7) 0.0175(3) Uani 1 1 d . . . . .
H19 H 0.346819 1.290222 0.081675 0.021 Uiso 1 1 calc R U . . .
C20 C 0.23360(19) 1.27510(15) 0.17246(7) 0.0161(3) Uani 1 1 d . . . . .
C21 C 0.20604(19) 1.17581(15) 0.22309(7) 0.0160(3) Uani 1 1 d . . . . .
H21 H 0.138836 1.210093 0.260898 0.019 Uiso 1 1 calc R U . . .
C22 C 0.27619(19) 1.02777(15) 0.21843(7) 0.0161(3) Uani 1 1 d . . . . .
H22 H 0.261203 0.961503 0.253664 0.019 Uiso 1 1 calc R U . . .
C23 C 0.1623(2) 1.43481(15) 0.17967(7) 0.0175(3) Uani 1 1 d . . . . .
N2 N 0.46719(18) 0.75486(13) 0.10217(6) 0.0192(3) Uani 1 1 d . . . . .
H2A H 0.512541 0.660739 0.099289 0.023 Uiso 1 1 calc R U . . .
H2B H 0.437775 0.807624 0.067479 0.023 Uiso 1 1 calc R U . . .
N3 N 0.48687(18) 0.73884(13) 0.21051(6) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.532318 0.644642 0.208193 0.023 Uiso 1 1 calc R U . . .
H3B H 0.470345 0.781340 0.247836 0.023 Uiso 1 1 calc R U . . .
N4 N 0.12242(18) 1.51965(13) 0.12950(6) 0.0211(3) Uani 1 1 d . . . . .
H4A H 0.078136 1.613536 0.134202 0.025 Uiso 1 1 calc R U . . .
H4B H 0.139897 1.482806 0.091077 0.025 Uiso 1 1 calc R U . . .
N5 N 0.13727(18) 1.48753(13) 0.23752(6) 0.0210(3) Uani 1 1 d . . . . .
H5A H 0.093087 1.581197 0.242958 0.025 Uiso 1 1 calc R U . . .
H5B H 0.164705 1.429152 0.270801 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3379(2) -0.12057(16) 0.39015(7) 0.0179(3) Uani 1 1 d . . . . .
C25 C 0.4188(2) -0.05473(15) 0.44675(7) 0.0170(3) Uani 1 1 d . . . . .
C26 C 0.6028(2) -0.10753(16) 0.46297(7) 0.0190(3) Uani 1 1 d . . . . .
H26 H 0.673778 -0.181264 0.437736 0.023 Uiso 1 1 calc R U . . .
C27 C 0.6833(2) -0.05378(16) 0.51540(7) 0.0195(3) Uani 1 1 d . . . . .
H27 H 0.808532 -0.090940 0.525638 0.023 Uiso 1 1 calc R U . . .
N6 N 0.15699(18) -0.07933(14) 0.37827(6) 0.0199(3) Uani 1 1 d . . . . .
H6A H 0.105255 -0.117833 0.346245 0.024 Uiso 1 1 calc R U . . .
H6B H 0.089449 -0.013628 0.402456 0.024 Uiso 1 1 calc R U . . .
O7 O 0.43663(15) -0.21277(12) 0.35696(5) 0.0230(2) Uani 1 1 d . . . . .
O8 O 0.77230(19) 0.55724(13) 0.00003(6) 0.0295(3) Uani 1 1 d D . . . .
H8A H 0.780(3) 0.481(2) 0.0288(10) 0.044 Uiso 1 1 d D U . . .
H8B H 0.826(5) 0.638(4) 0.0208(15) 0.078(9) Uiso 1 1 d . . . . .
O9 O 0.75208(16) 0.11516(12) 0.00067(5) 0.0228(2) Uani 1 1 d D . . . .
H9A H 0.756(3) 0.173(2) 0.0332(9) 0.034 Uiso 1 1 d D U . . .
H9B H 0.783(3) 0.0247(18) 0.0160(10) 0.034 Uiso 1 1 d D U . . .
O10 O 0.88636(17) -0.16833(12) 0.04735(5) 0.0246(2) Uani 1 1 d D . . . .
H10A H 0.887(3) -0.169(2) 0.0901(7) 0.037 Uiso 1 1 d D U . . .
H10B H 1.005(2) -0.162(2) 0.0359(10) 0.037 Uiso 1 1 d D U . . .
O11 O 0.77174(18) -0.41365(13) 0.35899(6) 0.0314(3) Uani 1 1 d D . . . .
H11A H 0.836(3) -0.361(2) 0.3319(10) 0.047 Uiso 1 1 d D U . . .
H11B H 0.660(2) -0.359(2) 0.3619(11) 0.047 Uiso 1 1 d D U . . .


_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
C1 C3 1.5149(18) . ?
C1 O1 1.2541(17) . ?
C1 O2 1.2547(17) . ?
C2 C5 1.5117(18) . ?
C2 O3 1.2511(17) . ?
C2 O4 1.2716(17) . ?
C3 C4 1.3976(18) . ?
C3 C8 1.3886(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3933(19) . ?
C5 C6 1.4019(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3878(19) . ?
C7 C8 1.3865(19) . ?
C7 N1 1.4561(17) . ?
C8 H8 0.9500 . ?
C9 C14 1.4830(18) 2_666 ?
C9 N1 1.4010(18) . ?
C9 O5 1.2181(17) . ?
C10 C11 1.4761(18) . ?
C10 N1 1.4049(18) . ?
C10 O6 1.2130(17) . ?
C11 C12 1.3800(19) . ?
C11 C15 1.4120(19) 2_666 ?
C12 H12 0.9500 . ?
C12 C13 1.4023(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3802(19) . ?
C14 C15 1.4129(19) . ?
C15 C15 1.409(3) 2_666 ?
C16 C17 1.4826(18) . ?
C16 N2 1.3084(19) . ?
C16 N3 1.3192(18) . ?
C17 C18 1.3964(19) . ?
C17 C22 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3871(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.396(2) . ?
C20 C21 1.395(2) . ?
C20 C23 1.4883(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.3823(19) . ?
C22 H22 0.9500 . ?
C23 N4 1.3087(19) . ?
C23 N5 1.3148(19) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
C24 C25 1.5098(19) . ?
C24 N6 1.3350(19) . ?
C24 O7 1.2386(18) . ?
C25 C26 1.398(2) . ?
C25 C27 1.399(2) 2_656 ?
C26 H26 0.9500 . ?
C26 C27 1.389(2) . ?
C27 H27 0.9500 . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
O8 H8A 0.902(16) . ?
O8 H8B 0.98(3) . ?
O9 H9A 0.878(15) . ?
O9 H9B 0.880(15) . ?
O10 H10A 0.898(15) . ?
O10 H10B 0.880(15) . ?
O11 H11A 0.879(16) . ?
O11 H11B 0.890(16) . ?

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
O1 C1 C3 116.85(12) . . ?
O1 C1 O2 124.93(13) . . ?
O2 C1 C3 118.21(12) . . ?
O3 C2 C5 118.65(12) . . ?
O3 C2 O4 124.11(12) . . ?
O4 C2 C5 117.19(12) . . ?
C4 C3 C1 121.50(12) . . ?
C8 C3 C1 119.56(12) . . ?
C8 C3 C4 118.94(12) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.77(12) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C2 119.17(12) . . ?
C4 C5 C6 119.82(12) . . ?
C6 C5 C2 120.84(12) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.95(12) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 N1 122.56(12) . . ?
C8 C7 C6 121.07(12) . . ?
C8 C7 N1 116.36(12) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.40(12) . . ?
C7 C8 H8 119.8 . . ?
N1 C9 C14 116.92(12) . 2_666 ?
O5 C9 C14 122.22(13) . 2_666 ?
O5 C9 N1 120.86(12) . . ?
N1 C10 C11 117.82(12) . . ?
O6 C10 C11 122.10(13) . . ?
O6 C10 N1 120.06(12) . . ?
C12 C11 C10 119.98(12) . . ?
C12 C11 C15 120.68(12) . 2_666 ?
C15 C11 C10 119.31(12) 2_666 . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.04(13) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.53(13) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.90(12) . 2_666 ?
C13 C14 C15 119.99(12) . . ?
C15 C14 C9 120.03(12) . 2_666 ?
C11 C15 C14 121.26(12) 2_666 . ?
C15 C15 C11 118.98(15) 2_666 2_666 ?
C15 C15 C14 119.77(15) 2_666 . ?
C9 N1 C7 118.87(11) . . ?
C9 N1 C10 124.25(11) . . ?
C10 N1 C7 115.93(11) . . ?
N2 C16 C17 119.65(12) . . ?
N2 C16 N3 120.77(13) . . ?
N3 C16 C17 119.57(13) . . ?
C18 C17 C16 120.59(13) . . ?
C22 C17 C16 119.83(12) . . ?
C22 C17 C18 119.56(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.25(13) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.96(13) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C23 121.34(13) . . ?
C21 C20 C19 119.60(12) . . ?
C21 C20 C23 119.06(13) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.24(13) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.34(13) . . ?
C21 C22 H22 119.8 . . ?
N4 C23 C20 120.54(13) . . ?
N4 C23 N5 121.02(13) . . ?
N5 C23 C20 118.42(13) . . ?
C16 N2 H2A 120.0 . . ?
C16 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C16 N3 H3A 120.0 . . ?
C16 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C23 N4 H4A 120.0 . . ?
C23 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C23 N5 H5A 120.0 . . ?
C23 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N6 C24 C25 118.04(12) . . ?
O7 C24 C25 120.43(13) . . ?
O7 C24 N6 121.51(13) . . ?
C26 C25 C24 118.33(13) . . ?
C26 C25 C27 118.55(13) . 2_656 ?
C27 C25 C24 123.11(13) 2_656 . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 120.99(13) . . ?
C27 C26 H26 119.5 . . ?
C25 C27 H27 119.8 2_656 . ?
C26 C27 C25 120.46(13) . 2_656 ?
C26 C27 H27 119.8 . . ?
C24 N6 H6A 120.0 . . ?
C24 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
H8A O8 H8B 105(2) . . ?
H9A O9 H9B 105.0(18) . . ?
H10A O10 H10B 102.7(18) . . ?
H11A O11 H11B 102(2) . . ?

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
C1 C3 C4 C5 179.43(12) . . . . ?
C1 C3 C8 C7 178.98(12) . . . . ?
C2 C5 C6 C7 173.12(12) . . . . ?
C3 C4 C5 C2 -173.64(12) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C4 C3 C8 C7 -2.0(2) . . . . ?
C4 C5 C6 C7 -2.0(2) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C5 C6 C7 N1 -178.98(12) . . . . ?
C6 C7 C8 C3 1.6(2) . . . . ?
C6 C7 N1 C9 68.20(17) . . . . ?
C6 C7 N1 C10 -122.47(14) . . . . ?
C8 C3 C4 C5 0.4(2) . . . . ?
C8 C7 N1 C9 -111.26(14) . . . . ?
C8 C7 N1 C10 58.06(16) . . . . ?
C9 C14 C15 C11 -4.4(2) 2_666 . . 2_666 ?
C9 C14 C15 C15 175.95(15) 2_666 . . 2_666 ?
C10 C11 C12 C13 -178.37(12) . . . . ?
C11 C10 N1 C7 -161.33(12) . . . . ?
C11 C10 N1 C9 7.35(19) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C9 -175.32(12) . . . 2_666 ?
C12 C13 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C11 178.95(13) . . . 2_666 ?
C13 C14 C15 C15 -0.7(2) . . . 2_666 ?
C14 C9 N1 C7 164.01(12) 2_666 . . . ?
C14 C9 N1 C10 -4.36(19) 2_666 . . . ?
C15 C11 C12 C13 -0.1(2) 2_666 . . . ?
N1 C7 C8 C3 -178.95(12) . . . . ?
N1 C10 C11 C12 173.92(12) . . . . ?
N1 C10 C11 C15 -4.35(19) . . . 2_666 ?
O1 C1 C3 C4 171.23(13) . . . . ?
O1 C1 C3 C8 -9.8(2) . . . . ?
O2 C1 C3 C4 -8.5(2) . . . . ?
O2 C1 C3 C8 170.46(13) . . . . ?
O3 C2 C5 C4 -16.44(19) . . . . ?
O3 C2 C5 C6 168.39(13) . . . . ?
O4 C2 C5 C4 161.27(12) . . . . ?
O4 C2 C5 C6 -13.90(19) . . . . ?
O5 C9 N1 C7 -15.13(19) . . . . ?
O5 C9 N1 C10 176.49(13) . . . . ?
O6 C10 C11 C12 -4.4(2) . . . . ?
O6 C10 C11 C15 177.28(13) . . . 2_666 ?
O6 C10 N1 C7 17.07(19) . . . . ?
O6 C10 N1 C9 -174.25(13) . . . . ?
C16 C17 C18 C19 -178.00(13) . . . . ?
C16 C17 C22 C21 179.90(12) . . . . ?
C17 C18 C19 C20 -1.4(2) . . . . ?
C18 C17 C22 C21 1.1(2) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C18 C19 C20 C23 179.79(13) . . . . ?
C19 C20 C21 C22 1.9(2) . . . . ?
C19 C20 C23 N4 25.0(2) . . . . ?
C19 C20 C23 N5 -156.19(14) . . . . ?
C20 C21 C22 C17 -2.4(2) . . . . ?
C21 C20 C23 N4 -155.18(14) . . . . ?
C21 C20 C23 N5 23.61(19) . . . . ?
C22 C17 C18 C19 0.8(2) . . . . ?
C23 C20 C21 C22 -177.91(12) . . . . ?
N2 C16 C17 C18 -25.8(2) . . . . ?
N2 C16 C17 C22 155.38(14) . . . . ?
N3 C16 C17 C18 153.68(14) . . . . ?
N3 C16 C17 C22 -25.1(2) . . . . ?
C24 C25 C26 C27 -178.49(13) . . . . ?
C25 C26 C27 C25 0.1(2) . . . 2_656 ?
C27 C25 C26 C27 -0.1(2) 2_656 . . . ?
N6 C24 C25 C26 174.22(13) . . . . ?
N6 C24 C25 C27 -4.1(2) . . . 2_656 ?
O7 C24 C25 C26 -4.1(2) . . . . ?
O7 C24 C25 C27 177.57(14) . . . 2_656 ?

_olex2_exptl_crystal_mounting_method 'fomblin on micromount'
_olex2_submission_original_sample_id HOF_2
_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
;
