# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_oxaz-136
_database_code_depnum_ccdc_archive 'CCDC 2304109'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-10-27 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N O6, 0.5(C6 H6)'
_chemical_formula_sum            'C27 H24 N O6'
_chemical_formula_weight         458.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H21NO6
_chemical_oxdiff_usercomment     OXAZ-136
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.2259(2)
_cell_length_b                   19.8037(2)
_cell_length_c                   7.83380(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.1260(10)
_cell_angle_gamma                90
_cell_volume                     2665.47(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17124
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      75.3130
_cell_measurement_theta_min      3.4640
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.064
_diffrn_reflns_theta_min         2.572
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00  35.00   0.50    4.03    --  -43.17  -2.00-156.00  314
  2  ω    -36.00 121.00   0.50    4.03    --   43.17  -2.00-156.00  314
  3  ω   -168.00 -11.00   0.50   17.12    --  -90.25   2.00  21.00  314
  4  ω     34.00 178.00   0.50   17.12    --  111.75   2.00  21.00  288
  5  ω     33.00 151.00   0.50   17.12    --  111.75  -2.00-156.00  236
  6  ω    -83.00 -14.00   0.50    4.03    --  -43.17 125.00-180.00  138
  7  ω    -29.00  43.00   0.50    4.03    --   43.17 -38.00 -90.00  144
  8  ω     40.00  80.00   0.50    4.03    --   43.17 -99.00-180.00   80
  9  ω     19.00  44.00   0.50    4.03    --   43.17   2.00  21.00   50
 10  ω   -115.00 -90.00   0.50   17.12    --  -90.25  -2.00-156.00   50
 11  ω     38.00  69.00   0.50   17.12    --  111.75 -61.00-120.00   62
 12  ω     65.00  91.00   0.50   17.12    --  111.75 -95.00  30.00   52
 13  ω     64.00  89.00   0.50   17.12    --  111.75 -77.00  60.00   50
 14  ω     45.00  75.00   0.50   17.12    --  111.75 -95.00 -30.00   60
 15  ω    140.00 166.00   0.50   17.12    --  111.75  45.00-150.00   52
 16  ω     39.00  90.00   0.50   17.12    --  111.75 -77.00 120.00  102
 17  ω    107.00 178.00   0.50   17.12    --  111.75 101.00  41.65  142
 18  ω     43.00  70.00   0.50   17.12    --  111.75 -61.00  30.00   54
 19  ω     54.00 108.00   0.50   17.12    --  111.75-112.00-157.16  108
 20  ω     37.00  64.00   0.50   17.12    --  111.75 -95.00  30.00   54
 21  ω     62.00 160.00   0.50   17.12    --  111.75  15.00  60.00  196
 22  ω     82.00 107.00   0.50   17.12    --  111.75-110.00 108.23   50
 23  ω     98.00 136.00   0.50   17.12    --  111.75  45.00-150.00   76
 24  ω     41.00 107.00   0.50   17.12    --  111.75-125.00  90.00  132
 25  ω     47.00  83.00   0.50   17.12    --  111.75-148.00-155.12   72
 26  ω     99.00 128.00   0.50   17.12    --  111.75-148.00-155.12   58
 27  ω     52.00  77.00   0.50   17.12    --  111.75-110.00 108.23   50
 28  ω     40.00 103.00   0.50   17.12    --  111.75 -95.00 120.00  126
 29  ω     56.00  91.00   0.50   17.12    --  111.75 -77.00-120.00   70
 30  ω     91.00 149.00   0.50   17.12    --  111.75  45.00-120.00  116
 31  ω    114.00 161.00   0.50   17.12    --  111.75  30.00-180.00   94
 32  ω     90.00 140.00   0.50   17.12    --  111.75  30.00 150.00  100
 33  ω     62.00  88.00   0.50   17.12    --  111.75 -77.00-180.00   52
 34  ω     87.00 112.00   0.50   17.12    --  111.75-125.00-150.00   50
 35  ω    111.00 144.00   0.50   17.12    --  111.75 -87.00  89.68   66
 36  ω     38.00  83.00   0.50   17.12    --  111.75 -95.00-180.00   90
 37  ω     39.00  71.00   0.50   17.12    --  111.75 -61.00   0.00   64
 38  ω     71.00 105.00   0.50   17.12    --  111.75 -95.00-120.00   68
 39  ω    116.00 142.00   0.50   17.12    --  111.75  80.00  53.47   52
 40  ω     91.00 177.00   0.50   17.12    --  111.75  61.00 -60.00  172
 41  ω     75.00 127.00   0.50   17.12    --  111.75   5.00 159.62  104
 42  ω     39.00  64.00   0.50   17.12    --  111.75 -77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0855761000
_diffrn_orient_matrix_UB_12      -0.0008867000
_diffrn_orient_matrix_UB_13      -0.0722617000
_diffrn_orient_matrix_UB_21      -0.0268639000
_diffrn_orient_matrix_UB_22      0.0018931000
_diffrn_orient_matrix_UB_23      0.1833932000
_diffrn_orient_matrix_UB_31      -0.0002415000
_diffrn_orient_matrix_UB_32      0.0777264000
_diffrn_orient_matrix_UB_33      -0.0053084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4965
_reflns_number_total             5572
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00104(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.041
_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)+(0.0700P)²+0.8706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_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. Restrained distances
 C25-C26 \\sim C26-C27 \\sim C25-C27_$2
 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6), C8(H8), C9(H9), C14(H14), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.54210(6) 0.54917(5) 0.68761(13) 0.0415(3) Uani 1 1 d . . . . .
O2 O 0.41958(7) 0.56115(5) 0.77707(15) 0.0468(3) Uani 1 1 d . . . . .
O3 O 0.54499(6) 0.32579(5) 0.72132(13) 0.0381(2) Uani 1 1 d . . . . .
O4 O 0.51398(7) 0.21901(5) 0.66174(15) 0.0461(3) Uani 1 1 d . . . . .
O5 O 0.64833(7) 0.17298(5) 0.84374(15) 0.0459(3) Uani 1 1 d . . . . .
H5 H 0.6102(14) 0.1464(13) 0.794(3) 0.076(7) Uiso 1 1 d . . . . .
O6 O 0.89055(7) 0.55053(7) 0.46405(16) 0.0560(3) Uani 1 1 d . . . . .
N1 N 0.48823(8) 0.46062(6) 0.80039(16) 0.0400(3) Uani 1 1 d . . . . .
C1 C 0.59610(9) 0.49632(7) 0.69152(18) 0.0395(3) Uani 1 1 d . . . . .
C2 C 0.56372(9) 0.44178(7) 0.76150(18) 0.0387(3) Uani 1 1 d . . . . .
C3 C 0.47659(9) 0.52633(7) 0.75721(19) 0.0409(3) Uani 1 1 d . . . . .
C4 C 0.67195(10) 0.51143(7) 0.63161(17) 0.0400(3) Uani 1 1 d . . . . .
C5 C 0.71523(10) 0.46178(7) 0.55316(19) 0.0443(4) Uani 1 1 d . . . . .
H5A H 0.694476 0.417609 0.537001 0.053 Uiso 1 1 calc R U . . .
C6 C 0.78723(11) 0.47662(8) 0.4997(2) 0.0476(4) Uani 1 1 d . . . . .
H6 H 0.816249 0.442638 0.447053 0.057 Uiso 1 1 calc R U . . .
C7 C 0.81830(10) 0.54158(8) 0.52223(19) 0.0463(4) Uani 1 1 d . . . . .
C8 C 0.77633(10) 0.59103(8) 0.59900(19) 0.0454(4) Uani 1 1 d . . . . .
H8 H 0.797313 0.635149 0.614491 0.054 Uiso 1 1 calc R U . . .
C9 C 0.70359(10) 0.57611(7) 0.65332(18) 0.0423(3) Uani 1 1 d . . . . .
H9 H 0.674819 0.610250 0.706001 0.051 Uiso 1 1 calc R U . . .
C10 C 0.92340(13) 0.61653(11) 0.4796(3) 0.0682(5) Uani 1 1 d . . . . .
H10A H 0.889725 0.648631 0.414236 0.102 Uiso 1 1 calc R U . . .
H10B H 0.975105 0.616458 0.434996 0.102 Uiso 1 1 calc R U . . .
H10C H 0.927956 0.629862 0.600426 0.102 Uiso 1 1 calc R U . . .
C11 C 0.59462(9) 0.37414(7) 0.79692(18) 0.0374(3) Uani 1 1 d . . . . .
C12 C 0.55986(9) 0.25803(7) 0.73288(18) 0.0368(3) Uani 1 1 d . . . . .
C13 C 0.63168(9) 0.23910(7) 0.82979(18) 0.0365(3) Uani 1 1 d . . . . .
C14 C 0.67906(9) 0.28649(7) 0.90351(18) 0.0382(3) Uani 1 1 d . . . . .
H14 H 0.725619 0.272946 0.966621 0.046 Uiso 1 1 calc R U . . .
C15 C 0.66067(9) 0.35727(7) 0.88872(18) 0.0374(3) Uani 1 1 d . . . . .
C16 C 0.71590(10) 0.40766(7) 0.9748(2) 0.0441(4) Uani 1 1 d . . . . .
H16A H 0.729587 0.393377 1.092962 0.066 Uiso 1 1 calc R U . . .
H16B H 0.690937 0.452122 0.975075 0.066 Uiso 1 1 calc R U . . .
H16C H 0.763160 0.410299 0.912585 0.066 Uiso 1 1 calc R U . . .
C17 C 0.43212(9) 0.42213(7) 0.89373(18) 0.0396(3) Uani 1 1 d . . . . .
H17A H 0.408862 0.452199 0.977182 0.048 Uiso 1 1 calc R U . . .
H17B H 0.459684 0.385278 0.958400 0.048 Uiso 1 1 calc R U . . .
C18 C 0.36747(10) 0.39205(8) 0.77387(19) 0.0446(4) Uani 1 1 d . . . . .
H18A H 0.342762 0.428344 0.702012 0.053 Uiso 1 1 calc R U . . .
H18B H 0.390099 0.358835 0.697101 0.053 Uiso 1 1 calc R U . . .
C19 C 0.30668(10) 0.35787(8) 0.87250(19) 0.0446(4) Uani 1 1 d . . . . .
C20 C 0.23373(11) 0.38617(9) 0.8816(2) 0.0506(4) Uani 1 1 d . . . . .
H20 H 0.222522 0.428332 0.827394 0.061 Uiso 1 1 calc R U . . .
C21 C 0.17643(13) 0.35424(12) 0.9683(2) 0.0680(6) Uani 1 1 d . . . . .
H21 H 0.126401 0.374106 0.972256 0.082 Uiso 1 1 calc R U . . .
C22 C 0.19308(18) 0.29308(13) 1.0488(2) 0.0794(8) Uani 1 1 d . . . . .
H22 H 0.154248 0.270373 1.107153 0.095 Uiso 1 1 calc R U . . .
C23 C 0.26539(18) 0.26572(11) 1.0439(2) 0.0773(8) Uani 1 1 d . . . . .
H23 H 0.276733 0.224237 1.101240 0.093 Uiso 1 1 calc R U . . .
C24 C 0.32262(13) 0.29684(9) 0.9575(2) 0.0598(5) Uani 1 1 d . . . . .
H24 H 0.372685 0.276837 0.955842 0.072 Uiso 1 1 calc R U . . .
C25 C 0.93154(14) 0.48919(16) 0.9063(3) 0.0857(8) Uani 1 1 d D . . . .
H25 H 0.883610 0.481599 0.841361 0.103 Uiso 1 1 calc R U . . .
C26 C 0.93468(13) 0.48481(16) 1.0817(3) 0.0884(8) Uani 1 1 d D . . . .
H26 H 0.889049 0.474233 1.137525 0.106 Uiso 1 1 calc R U . . .
C27 C 1.00330(11) 0.49565(11) 1.1756(3) 0.0649(5) Uani 1 1 d D . . . .
H27 H 1.005763 0.492681 1.296930 0.078 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 1.3992(17) . ?
O1 C3 1.365(2) . ?
O2 C3 1.2190(19) . ?
O3 C11 1.3877(16) . ?
O3 C12 1.3679(16) . ?
O4 C12 1.2119(17) . ?
O5 H5 0.91(3) . ?
O5 C13 1.3432(16) . ?
O6 C7 1.367(2) . ?
O6 C10 1.426(2) . ?
N1 C2 1.407(2) . ?
N1 C3 1.3558(18) . ?
N1 C17 1.467(2) . ?
C1 C2 1.350(2) . ?
C1 C4 1.451(2) . ?
C2 C11 1.4605(18) . ?
C4 C5 1.402(2) . ?
C4 C9 1.398(2) . ?
C5 H5A 0.9500 . ?
C5 C6 1.369(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.400(2) . ?
C7 C8 1.381(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.344(2) . ?
C12 C13 1.453(2) . ?
C13 C14 1.346(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.4399(19) . ?
C15 C16 1.5046(19) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.525(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.506(2) . ?
C19 C20 1.382(3) . ?
C19 C24 1.398(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.361(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.374(2) . ?
C25 C27 1.366(2) 3_767 ?
C26 H26 0.9500 . ?
C26 C27 1.364(2) . ?
C27 H27 0.9500 . ?

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
C3 O1 C1 108.10(11) . . ?
C12 O3 C11 122.82(11) . . ?
C13 O5 H5 112.8(15) . . ?
C7 O6 C10 117.10(15) . . ?
C2 N1 C17 128.50(12) . . ?
C3 N1 C2 108.84(12) . . ?
C3 N1 C17 122.15(13) . . ?
O1 C1 C4 116.83(12) . . ?
C2 C1 O1 108.30(14) . . ?
C2 C1 C4 134.78(14) . . ?
N1 C2 C11 122.14(13) . . ?
C1 C2 N1 106.92(13) . . ?
C1 C2 C11 130.95(15) . . ?
O2 C3 O1 124.06(13) . . ?
O2 C3 N1 128.11(15) . . ?
N1 C3 O1 107.82(13) . . ?
C5 C4 C1 121.11(13) . . ?
C9 C4 C1 120.13(14) . . ?
C9 C4 C5 118.75(15) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 C4 120.36(14) . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.35(16) . . ?
C7 C6 H6 119.8 . . ?
O6 C7 C6 115.23(15) . . ?
O6 C7 C8 124.82(15) . . ?
C8 C7 C6 119.96(16) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.78(14) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 119.6 . . ?
C8 C9 C4 120.80(15) . . ?
C8 C9 H9 119.6 . . ?
O6 C10 H10A 109.5 . . ?
O6 C10 H10B 109.5 . . ?
O6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C2 110.29(12) . . ?
C15 C11 O3 121.92(12) . . ?
C15 C11 C2 127.79(13) . . ?
O3 C12 C13 115.85(12) . . ?
O4 C12 O3 118.82(13) . . ?
O4 C12 C13 125.32(13) . . ?
O5 C13 C12 117.56(12) . . ?
O5 C13 C14 121.69(13) . . ?
C14 C13 C12 120.74(13) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.40(13) . . ?
C15 C14 H14 119.3 . . ?
C11 C15 C14 117.26(13) . . ?
C11 C15 C16 123.97(13) . . ?
C14 C15 C16 118.77(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
N1 C17 C18 111.97(12) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 C17 111.32(12) . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C20 C19 C18 120.81(14) . . ?
C20 C19 C24 118.32(17) . . ?
C24 C19 C18 120.87(17) . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.37(18) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.2 . . ?
C22 C23 C24 121.6(2) . . ?
C24 C23 H23 119.2 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
C26 C25 H25 119.7 . . ?
C27 C25 H25 119.7 3_767 . ?
C27 C25 C26 120.61(19) 3_767 . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C27 H27 120.3 3_767 . ?
C26 C27 C25 119.40(18) . 3_767 ?
C26 C27 H27 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O2 0.91(3) 1.84(3) 2.6477(15) 147(2) 2_646 yes

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 N1 0.53(15) . . . . ?
O1 C1 C2 C11 -179.34(13) . . . . ?
O1 C1 C4 C5 -149.06(13) . . . . ?
O1 C1 C4 C9 31.68(18) . . . . ?
O3 C11 C15 C14 1.1(2) . . . . ?
O3 C11 C15 C16 -179.27(13) . . . . ?
O3 C12 C13 O5 -179.90(12) . . . . ?
O3 C12 C13 C14 0.6(2) . . . . ?
O4 C12 C13 O5 -0.9(2) . . . . ?
O4 C12 C13 C14 179.65(15) . . . . ?
O5 C13 C14 C15 -179.70(13) . . . . ?
O6 C7 C8 C9 -179.88(13) . . . . ?
N1 C2 C11 O3 54.64(17) . . . . ?
N1 C2 C11 C15 -125.04(17) . . . . ?
N1 C17 C18 C19 -175.07(12) . . . . ?
C1 O1 C3 O2 177.62(13) . . . . ?
C1 O1 C3 N1 -1.25(15) . . . . ?
C1 C2 C11 O3 -125.50(16) . . . . ?
C1 C2 C11 C15 54.8(2) . . . . ?
C1 C4 C5 C6 -179.00(13) . . . . ?
C1 C4 C9 C8 179.10(13) . . . . ?
C2 N1 C3 O1 1.59(15) . . . . ?
C2 N1 C3 O2 -177.23(14) . . . . ?
C2 N1 C17 C18 -103.99(16) . . . . ?
C2 C1 C4 C5 34.8(2) . . . . ?
C2 C1 C4 C9 -144.41(17) . . . . ?
C2 C11 C15 C14 -179.26(14) . . . . ?
C2 C11 C15 C16 0.4(3) . . . . ?
C3 O1 C1 C2 0.43(15) . . . . ?
C3 O1 C1 C4 -176.65(12) . . . . ?
C3 N1 C2 C1 -1.32(16) . . . . ?
C3 N1 C2 C11 178.57(13) . . . . ?
C3 N1 C17 C18 85.16(17) . . . . ?
C4 C1 C2 N1 176.86(15) . . . . ?
C4 C1 C2 C11 -3.0(3) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
C5 C6 C7 O6 179.98(13) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C4 0.1(2) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C10 O6 C7 C6 178.12(15) . . . . ?
C10 O6 C7 C8 -2.0(2) . . . . ?
C11 O3 C12 O4 -179.26(13) . . . . ?
C11 O3 C12 C13 -0.15(19) . . . . ?
C12 O3 C11 C2 179.57(12) . . . . ?
C12 O3 C11 C15 -0.7(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C11 -0.6(2) . . . . ?
C13 C14 C15 C16 179.72(14) . . . . ?
C17 N1 C2 C1 -173.14(13) . . . . ?
C17 N1 C2 C11 6.7(2) . . . . ?
C17 N1 C3 O1 174.03(11) . . . . ?
C17 N1 C3 O2 -4.8(2) . . . . ?
C17 C18 C19 C20 108.20(16) . . . . ?
C17 C18 C19 C24 -71.64(19) . . . . ?
C18 C19 C20 C21 178.24(15) . . . . ?
C18 C19 C24 C23 -178.56(15) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C19 C24 C23 1.6(2) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C23 C24 C19 0.0(3) . . . . ?
C24 C19 C20 C21 -1.9(2) . . . . ?
C25 C26 C27 C25 0.0(5) . . . 3_767 ?
C27 C25 C26 C27 0.0(5) 3_767 . . . ?

_smtbx_masks_special_details     ?
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 -0.087 0.250 -0.728 257.7 60.4 ?
2 0.087 0.750 -0.549 257.7 60.5 ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.461
