# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lwp-20191021
_database_code_depnum_ccdc_archive 'CCDC 2009735'
loop_
_audit_author_name
_audit_author_address
b
;a 
China
;
_audit_update_record             
;
2020-06-15 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;
_audit_creation_date             2020-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        lwp
_chemical_formula_moiety         'C18 H16 N2 O7'
_chemical_formula_sum            'C18 H16 N2 O7'
_chemical_formula_weight         372.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.48180(10)
_cell_length_b                   10.0714(2)
_cell_length_c                   23.3470(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1759.25(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15045
_cell_measurement_temperature    292.7(2)
_cell_measurement_theta_max      70.8470
_cell_measurement_theta_min      4.7620
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31254
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.663
_diffrn_reflns_theta_min         3.787
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.7(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  31.00   1.00    1.00    --  -35.62  67.00-123.00   88
  2  ω    -31.00  57.00   1.00    1.00    --   35.62 -67.00 102.00   88
  3  ω     41.00 128.00   1.00    3.11    --  107.12 -67.00 102.00   87
  4  ω     39.00 134.00   1.00    3.11    --  107.12 -78.00 -15.00   95
  5  ω     40.00 134.00   1.00    3.11    --  107.12 -77.00-129.00   94
  6  ω    -62.00  32.00   1.00    1.00    --  -35.62  77.00  -4.00   94
  7  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00-180.00   73
  8  ω     19.00 103.00   1.00    1.00    --   35.62  57.00 -60.00   84
  9  ω     55.00 108.00   1.00    1.00    --   35.62-178.00 150.00   53
 10  ω     90.00 176.00   1.00    3.11    --  107.12  45.00 150.00   86
 11  ω     90.00 176.00   1.00    3.11    --  107.12  45.00-180.00   86
 12  ω     89.00 174.00   1.00    3.11    --  107.12  61.00  90.00   85
 13  ω     37.00 113.00   1.00    3.11    --  107.12-111.00-120.00   76
 14  ω    100.00 177.00   1.00    3.11    --  107.12 111.00 -60.00   77
 15  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -30.00   94
 16  ω     19.00 103.00   1.00    1.00    --   35.62  57.00  90.00   84
 17  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 120.00   94
 18  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-120.00   84
 19  ω     19.00 103.00   1.00    1.00    --   35.62  57.00  30.00   84
 20  ω     86.00 177.00   1.00    3.11    --  107.12  30.00  30.00   91
 21  ω     37.00 113.00   1.00    3.11    --  107.12-111.00  60.00   76
 22  ω     86.00 177.00   1.00    3.11    --  107.12  30.00 -90.00   91
 23  ω     80.00 175.00   1.00    3.11    --  107.12  77.00 -90.00   95
 24  ω     89.00 174.00   1.00    3.11    --  107.12  61.00  60.00   85
 25  ω     80.00 175.00   1.00    3.11    --  107.12  77.00-150.00   95
 26  ω     80.00 175.00   1.00    3.11    --  107.12  77.00  30.00   95
 27  ω     80.00 175.00   1.00    3.11    --  107.12  77.00 -30.00   95
 28  ω     90.00 176.00   1.00    3.11    --  107.12  45.00 120.00   86
 29  ω     86.00 177.00   1.00    3.11    --  107.12  30.00 -30.00   91
 30  ω      6.00 107.00   1.00    1.00    --   35.62  19.00  30.00  101
 31  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
 32  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-180.00   94
 33  ω    -24.00  63.00   1.00    1.00    --   35.62 -78.00 -15.00   87
 34  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
 35  ω     80.00 175.00   1.00    3.11    --  107.12  77.00  60.00   95
 36  ω     89.00 174.00   1.00    3.11    --  107.12  61.00 120.00   85
 37  ω     80.00 175.00   1.00    3.11    --  107.12  77.00-180.00   95
 38  ω     89.00 174.00   1.00    3.11    --  107.12  61.00 150.00   85
 39  ω     80.00 175.00   1.00    3.11    --  107.12  77.00 -60.00   95
 40  ω     80.00 175.00   1.00    3.11    --  107.12  77.00-120.00   95
 41  ω     89.00 174.00   1.00    3.11    --  107.12  61.00 -30.00   85
 42  ω     86.00 161.00   1.00    3.11    --  107.12  30.00 -60.00   75
 43  ω     80.00 175.00   1.00    3.11    --  107.12  77.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684099000
_diffrn_orient_matrix_UB_12      0.0874939000
_diffrn_orient_matrix_UB_13      -0.0494708000
_diffrn_orient_matrix_UB_21      0.1585519000
_diffrn_orient_matrix_UB_22      0.0954644000
_diffrn_orient_matrix_UB_23      0.0089350000
_diffrn_orient_matrix_UB_31      0.1121038000
_diffrn_orient_matrix_UB_32      -0.0814388000
_diffrn_orient_matrix_UB_33      -0.0428104000
_diffrn_oxdiff_digest_frames     
;
01806c757ea229f8624f476f2fc4e0b91a0003727d6
;
_diffrn_oxdiff_digest_hkl        
;
01db0e53f227bad8a4054566ca4302ffd0715a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3259
_reflns_number_total             3434
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.037
_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)+(0.0695P)²+0.1171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C2(H2), C3(H3), C26(H26), C24(H24), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O15 O 0.4932(2) 0.3702(2) 0.43413(7) 0.0678(5) Uani 1 1 d . . . . .
O11 O 0.6809(3) 0.18726(17) 0.36969(8) 0.0661(5) Uani 1 1 d . . . . .
O20 O 0.5068(2) 0.64716(19) 0.33748(8) 0.0663(5) Uani 1 1 d . . . . .
N1 N 0.2694(3) 0.52792(18) 0.30393(7) 0.0492(4) Uani 1 1 d . . . . .
O17 O 0.2153(2) 0.3472(3) 0.40322(8) 0.0832(7) Uani 1 1 d . . . . .
N5 N 0.2310(3) 0.74054(19) 0.34036(8) 0.0565(5) Uani 1 1 d . . . . .
O13 O 0.7419(3) 0.3106(3) 0.29382(10) 0.0929(8) Uani 1 1 d . . . . .
O21 O -0.0391(4) 0.8406(3) 0.33995(13) 0.1028(8) Uani 1 1 d . . . . .
C7 C 0.3893(3) 0.4203(2) 0.28960(8) 0.0497(5) Uani 1 1 d . . . . .
H7 H 0.478246 0.441067 0.260099 0.060 Uiso 1 1 calc R . . . .
C10 C 0.6417(3) 0.2779(2) 0.33106(9) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.3481(3) 0.6393(2) 0.32786(9) 0.0503(5) Uani 1 1 d . . . . .
C14 C 0.3717(3) 0.3470(2) 0.39455(9) 0.0521(5) Uani 1 1 d . . . . .
C8 C 0.4536(3) 0.3268(2) 0.33674(9) 0.0481(5) Uani 1 1 d . . . . .
C22 C 0.3112(3) 0.8752(2) 0.42662(10) 0.0537(5) Uani 1 1 d . . . . .
O19 O 0.3663(5) 0.9452(2) 0.33178(10) 0.1183(12) Uani 1 1 d . . . . .
C9 C 0.3261(3) 0.2823(3) 0.28994(11) 0.0598(6) Uani 1 1 d . . . . .
H9A H 0.372326 0.223098 0.260725 0.072 Uiso 1 1 calc R . . . .
H9B H 0.202572 0.266555 0.300544 0.072 Uiso 1 1 calc R . . . .
C27 C 0.2335(3) 0.7812(3) 0.46205(10) 0.0600(6) Uani 1 1 d . . . . .
H27 H 0.179977 0.706335 0.446247 0.072 Uiso 1 1 calc R . . . .
C2 C 0.0884(3) 0.5206(3) 0.29392(9) 0.0544(5) Uani 1 1 d . . . . .
H2 H 0.041810 0.443159 0.278177 0.065 Uiso 1 1 calc R . . . .
C3 C -0.0220(4) 0.6196(3) 0.30584(10) 0.0626(6) Uani 1 1 d . . . . .
H3 H -0.143854 0.610082 0.299084 0.075 Uiso 1 1 calc R . . . .
C4 C 0.0451(4) 0.7408(3) 0.32899(11) 0.0677(7) Uani 1 1 d . . . . .
C26 C 0.2352(4) 0.7981(3) 0.52068(11) 0.0727(7) Uani 1 1 d . . . . .
H26 H 0.182702 0.734708 0.544247 0.087 Uiso 1 1 calc R . . . .
C18 C 0.3100(4) 0.8640(2) 0.36376(11) 0.0681(7) Uani 1 1 d . . . . .
C24 C 0.3951(4) 1.0012(3) 0.50970(14) 0.0779(8) Uani 1 1 d . . . . .
H24 H 0.450729 1.074691 0.525970 0.093 Uiso 1 1 calc R . . . .
C23 C 0.3940(4) 0.9857(3) 0.45089(13) 0.0661(6) Uani 1 1 d . . . . .
H23 H 0.448315 1.048780 0.427582 0.079 Uiso 1 1 calc R . . . .
C16 C 0.4277(4) 0.3962(4) 0.49131(11) 0.0792(8) Uani 1 1 d . . . . .
H16A H 0.374105 0.482735 0.492535 0.119 Uiso 1 1 calc GR . . . .
H16B H 0.525296 0.392491 0.517945 0.119 Uiso 1 1 calc GR . . . .
H16C H 0.340147 0.330519 0.501405 0.119 Uiso 1 1 calc GR . . . .
C25 C 0.3141(4) 0.9081(4) 0.54433(12) 0.0773(8) Uani 1 1 d . . . . .
H25 H 0.312841 0.919943 0.583831 0.093 Uiso 1 1 calc R . . . .
C12 C 0.8514(5) 0.1228(4) 0.36380(13) 0.0876(10) Uani 1 1 d . . . . .
H12A H 0.864635 0.090690 0.325324 0.131 Uiso 1 1 calc GR . . . .
H12B H 0.858309 0.049654 0.390063 0.131 Uiso 1 1 calc GR . . . .
H12C H 0.945035 0.185084 0.372086 0.131 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O15 C14 1.317(3) . ?
O15 C16 1.446(3) . ?
O11 C10 1.316(3) . ?
O11 C12 1.438(3) . ?
O20 C6 1.211(3) . ?
N1 C7 1.446(3) . ?
N1 C6 1.385(3) . ?
N1 C2 1.376(3) . ?
O17 C14 1.188(3) . ?
N5 C6 1.375(3) . ?
N5 C4 1.415(4) . ?
N5 C18 1.481(3) . ?
O13 C10 1.194(3) . ?
O21 C4 1.214(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.526(3) . ?
C7 C9 1.468(3) . ?
C10 C8 1.497(3) . ?
C14 C8 1.496(3) . ?
C8 C9 1.518(3) . ?
C22 C27 1.385(3) . ?
C22 C18 1.472(3) . ?
C22 C23 1.394(4) . ?
O19 C18 1.185(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C27 H27 0.9300 . ?
C27 C26 1.379(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.324(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.426(4) . ?
C26 H26 0.9300 . ?
C26 C25 1.371(5) . ?
C24 H24 0.9300 . ?
C24 C23 1.382(4) . ?
C24 C25 1.379(5) . ?
C23 H23 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C25 H25 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O15 C16 116.5(2) . . ?
C10 O11 C12 116.4(2) . . ?
C6 N1 C7 115.88(18) . . ?
C2 N1 C7 122.09(19) . . ?
C2 N1 C6 122.0(2) . . ?
C6 N5 C4 126.0(2) . . ?
C6 N5 C18 116.5(2) . . ?
C4 N5 C18 117.4(2) . . ?
N1 C7 H7 115.1 . . ?
N1 C7 C8 119.41(16) . . ?
N1 C7 C9 120.53(19) . . ?
C8 C7 H7 115.1 . . ?
C9 C7 H7 115.1 . . ?
C9 C7 C8 60.89(16) . . ?
O11 C10 C8 112.17(19) . . ?
O13 C10 O11 123.4(2) . . ?
O13 C10 C8 124.3(2) . . ?
O20 C6 N1 123.0(2) . . ?
O20 C6 N5 122.5(2) . . ?
N5 C6 N1 114.5(2) . . ?
O15 C14 C8 111.97(19) . . ?
O17 C14 O15 124.1(2) . . ?
O17 C14 C8 123.9(2) . . ?
C10 C8 C7 115.83(17) . . ?
C10 C8 C9 115.45(18) . . ?
C14 C8 C7 115.95(18) . . ?
C14 C8 C10 120.65(19) . . ?
C14 C8 C9 115.57(19) . . ?
C9 C8 C7 57.66(15) . . ?
C27 C22 C18 122.7(2) . . ?
C27 C22 C23 119.3(2) . . ?
C23 C22 C18 118.0(2) . . ?
C7 C9 C8 61.45(15) . . ?
C7 C9 H9A 117.6 . . ?
C7 C9 H9B 117.6 . . ?
C8 C9 H9A 117.6 . . ?
C8 C9 H9B 117.6 . . ?
H9A C9 H9B 114.7 . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.3(3) . . ?
C26 C27 H27 119.9 . . ?
N1 C2 H2 118.7 . . ?
C3 C2 N1 122.5(2) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
N5 C4 C3 114.6(2) . . ?
O21 C4 N5 118.2(3) . . ?
O21 C4 C3 127.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C22 C18 N5 115.8(2) . . ?
O19 C18 N5 119.3(2) . . ?
O19 C18 C22 125.0(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C25 C24 C23 120.2(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
O15 C16 H16A 109.5 . . ?
O15 C16 H16B 109.5 . . ?
O15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O15 C14 C8 C7 -122.7(2) . . . . ?
O15 C14 C8 C10 25.7(3) . . . . ?
O15 C14 C8 C9 172.6(2) . . . . ?
O11 C10 C8 C7 -173.26(18) . . . . ?
O11 C10 C8 C14 38.3(3) . . . . ?
O11 C10 C8 C9 -108.6(2) . . . . ?
N1 C7 C8 C10 -144.30(19) . . . . ?
N1 C7 C8 C14 5.6(3) . . . . ?
N1 C7 C8 C9 110.7(2) . . . . ?
N1 C7 C9 C8 -108.9(2) . . . . ?
N1 C2 C3 C4 1.2(4) . . . . ?
O17 C14 C8 C7 54.5(4) . . . . ?
O17 C14 C8 C10 -157.1(3) . . . . ?
O17 C14 C8 C9 -10.2(4) . . . . ?
O13 C10 C8 C7 2.5(4) . . . . ?
O13 C10 C8 C14 -146.0(3) . . . . ?
O13 C10 C8 C9 67.1(4) . . . . ?
C7 N1 C6 O20 -1.3(3) . . . . ?
C7 N1 C6 N5 179.23(17) . . . . ?
C7 N1 C2 C3 -178.6(2) . . . . ?
C10 C8 C9 C7 -105.6(2) . . . . ?
C6 N1 C7 C8 79.8(2) . . . . ?
C6 N1 C7 C9 151.4(2) . . . . ?
C6 N1 C2 C3 0.7(3) . . . . ?
C6 N5 C4 O21 -176.3(2) . . . . ?
C6 N5 C4 C3 4.2(4) . . . . ?
C6 N5 C18 C22 -95.0(3) . . . . ?
C6 N5 C18 O19 85.1(4) . . . . ?
C14 C8 C9 C7 105.7(2) . . . . ?
C22 C27 C26 C25 -0.1(5) . . . . ?
C9 C7 C8 C10 105.0(2) . . . . ?
C9 C7 C8 C14 -105.1(2) . . . . ?
C27 C22 C18 N5 -4.1(4) . . . . ?
C27 C22 C18 O19 175.8(4) . . . . ?
C27 C22 C23 C24 -1.0(4) . . . . ?
C27 C26 C25 C24 -1.2(5) . . . . ?
C2 N1 C7 C8 -100.8(2) . . . . ?
C2 N1 C7 C9 -29.3(3) . . . . ?
C2 N1 C6 O20 179.3(2) . . . . ?
C2 N1 C6 N5 -0.2(3) . . . . ?
C2 C3 C4 N5 -3.4(4) . . . . ?
C2 C3 C4 O21 177.2(3) . . . . ?
C4 N5 C6 O20 178.1(2) . . . . ?
C4 N5 C6 N1 -2.5(3) . . . . ?
C4 N5 C18 C22 89.5(3) . . . . ?
C4 N5 C18 O19 -90.4(4) . . . . ?
C18 N5 C6 O20 3.0(3) . . . . ?
C18 N5 C6 N1 -177.51(17) . . . . ?
C18 N5 C4 O21 -1.3(4) . . . . ?
C18 N5 C4 C3 179.2(2) . . . . ?
C18 C22 C27 C26 -178.6(3) . . . . ?
C18 C22 C23 C24 178.8(3) . . . . ?
C23 C22 C27 C26 1.2(4) . . . . ?
C23 C22 C18 N5 176.1(2) . . . . ?
C23 C22 C18 O19 -4.0(5) . . . . ?
C23 C24 C25 C26 1.4(5) . . . . ?
C16 O15 C14 O17 0.5(4) . . . . ?
C16 O15 C14 C8 177.7(2) . . . . ?
C25 C24 C23 C22 -0.3(4) . . . . ?
C12 O11 C10 O13 -2.7(4) . . . . ?
C12 O11 C10 C8 173.1(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.783
