# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_str0216lt100kcu
_database_code_depnum_ccdc_archive 'CCDC 1919282'
loop_
_audit_author_name
_audit_author_address
'Vladimir N. Nesterov'
;Department of Chemistry, University of North Texas
United States of America
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H19NO5
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.94010(10)
_cell_length_b                   10.34330(10)
_cell_length_c                   9.39150(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.4510(10)
_cell_angle_gamma                90
_cell_volume                     844.611(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23615
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5150
_cell_measurement_theta_min      4.2890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24355
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.758
_diffrn_reflns_theta_min         4.842
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  35.00   0.50    1.00    --   47.20 -40.00 -35.00  122
  2  ω     31.00 121.00   0.50    1.00    --   47.20  57.00-120.00  180
  3  ω     90.00 178.00   0.50    0.50    --  107.75  61.00-180.00  176
  4  ω     93.00 178.00   0.50    0.50    --  107.75  15.00-150.00  170
  5  ω     90.00 178.00   0.50    0.50    --  107.75  61.00 -90.00  176
  6  ω     94.00 178.00   0.50    0.50    --  107.75  45.00-120.00  168
  7  ω     94.00 178.00   0.50    0.50    --  107.75  45.00 -90.00  168
  8  ω     85.00 178.00   0.50    0.50    --  107.75  77.00   0.00  186
  9  ω     94.00 178.00   0.50    0.50    --  107.75  40.00 118.00  168
 10  ω     93.00 178.00   0.50    0.50    --  107.75  15.00   0.00  170
 11  ω     90.00 178.00   0.50    0.50    --  107.75  61.00-120.00  176
 12  ω     85.00 178.00   0.50    0.50    --  107.75  77.00-120.00  186
 13  ω     85.00 178.00   0.50    0.50    --  107.75  77.00-150.00  186
 14  ω     90.00 178.00   0.50    0.50    --  107.75  61.00-150.00  176
 15  ω     85.00 178.00   0.50    0.50    --  107.75  77.00-180.00  186
 16  ω     31.00 121.00   0.50    1.00    --   47.20  57.00-180.00  180
 17  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00 -30.00   54
 18  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00  30.00  124
 19  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00 150.00  124
 20  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00  90.00  124
 21  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00   0.00  124
 22  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00 120.00   54
 23  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00  60.00   54
 24  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00  60.00  124
 25  ω     34.00 117.00   0.50    0.50    --  107.75-125.00   0.00  166
 26  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00-150.00  124
 27  ω     34.00 109.00   0.50    0.50    --  107.75 -94.00 -30.00  150
 28  ω     34.00  96.00   0.50    0.50    --  107.75 -77.00-120.00  124
 29  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00-180.00   54
 30  ω     30.00  96.00   0.50    1.00    --   47.20-125.00-180.00  132
 31  ω     30.00 120.00   0.50    1.00    --   47.20  60.00 -34.30  180
 32  ω     34.00 121.00   0.50    1.00    --   47.20  40.00 118.00  174
 33  ω     90.00 178.00   0.50    0.50    --  107.75  61.00 150.00  176
 34  ω     85.00 178.00   0.50    0.50    --  107.75  77.00 150.00  186
 35  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00 150.00   54
 36  ω     31.00 121.00   0.50    1.00    --   47.20  57.00  90.00  180
 37  ω     31.00 121.00   0.50    1.00    --   47.20  57.00 -60.00  180
 38  ω     27.00 121.00   0.50    1.00    --   47.20  69.00   3.56  188
 39  ω    -55.00 -13.00   0.50    0.50    --  -86.25  40.00 118.00   84
 40  ω    -55.00  26.00   0.50    1.00    --  -47.20  40.00 118.00  162
 41  ω    -92.00 -13.00   0.50    0.50    --  -86.25 125.00 150.00  158
 42  ω   -121.00 -33.00   0.50    1.00    --  -47.20 -40.00 -35.00  176
 43  ω   -121.00 -85.00   0.50    1.00    --  -47.20 -77.00-120.00   72
 44  ω   -160.00 -72.00   0.50    0.50    --  -86.25 -40.00 -35.00  176
 45  ω   -121.00 -31.00   0.50    1.00    --  -47.20 -57.00  60.00  180
 46  ω   -121.00 -78.00   0.50    1.00    --  -47.20-125.00 120.00   86
 47  ω   -121.00 -31.00   0.50    1.00    --  -47.20 -57.00 120.00  180
 48  ω   -160.00 -67.00   0.50    0.50    --  -86.25 -65.00-134.40  186
 49  ω   -160.00 -67.00   0.50    0.50    --  -86.25 -65.00-167.73  186
 50  ω   -160.00 -71.00   0.50    0.50    --  -86.25 -56.00-162.83  178
 51  ω   -160.00 -68.00   0.50    0.50    --  -86.25 -63.00 -97.97  184
 52  ω   -160.00 -70.00   0.50    0.50    --  -86.25 -59.00-127.64  180
 53  ω   -160.00 -71.00   0.50    0.50    --  -86.25 -54.00 162.48  178
 54  ω   -160.00 -69.00   0.50    0.50    --  -86.25 -61.00 150.00  182
;
_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      -0.0250149000
_diffrn_orient_matrix_UB_12      -0.0566710000
_diffrn_orient_matrix_UB_13      -0.1554979000
_diffrn_orient_matrix_UB_21      -0.1594413000
_diffrn_orient_matrix_UB_22      -0.0499868000
_diffrn_orient_matrix_UB_23      0.0103931000
_diffrn_orient_matrix_UB_31      -0.0730674000
_diffrn_orient_matrix_UB_32      0.1283451000
_diffrn_orient_matrix_UB_33      -0.0645514000
_diffrn_oxdiff_ac3_digest_frames 
;
01a498c46c2aae4cac3c71311375d44f600003231a7
;
_diffrn_oxdiff_ac3_digest_hkl    
;
012a8fe14af72073b8257c4491dc3bf67fe49d
;
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3523
_reflns_number_total             3535
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.068
_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)+(0.0405P)²+0.1436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0666
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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 0.83514(12) 0.64093(11) 0.54477(12) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.54850(14) 0.84324(12) 0.95239(13) 0.0240(3) Uani 1 1 d . . . . .
H2 H 0.466548 0.806565 0.949627 0.036 Uiso 1 1 calc GR . . . .
O3 O 0.80631(13) 0.44724(12) 0.27119(12) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.33629(15) 0.67131(13) 0.86772(16) 0.0317(3) Uani 1 1 d . . . . .
O5 O 0.35442(12) 0.53116(12) 0.69162(13) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.83080(16) 0.40829(14) 0.54556(15) 0.0209(3) Uani 1 1 d . . . . .
H1 H 0.871719 0.370659 0.482287 0.025 Uiso 1 1 calc R . . . .
C1 C 0.76601(17) 0.69989(15) 0.64503(16) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.83213(18) 0.80044(16) 0.73527(17) 0.0194(3) Uani 1 1 d . . . . .
H2A H 0.925362 0.836358 0.727776 0.023 Uiso 1 1 calc R . . . .
C3 C 0.75478(19) 0.84587(16) 0.83722(17) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.796630 0.913650 0.898758 0.024 Uiso 1 1 calc R . . . .
C4 C 0.61534(19) 0.79168(15) 0.84908(17) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.54874(18) 0.68901(15) 0.75660(17) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.62736(17) 0.64477(15) 0.65191(16) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.59032(16) 0.53941(16) 0.53797(16) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.560723 0.459857 0.581033 0.020 Uiso 1 1 calc R . . . .
C8 C 0.46168(18) 0.58250(18) 0.40679(18) 0.0232(3) Uani 1 1 d . . . . .
H8A H 0.424933 0.508128 0.345716 0.028 Uiso 1 1 calc R . . . .
H8B H 0.376205 0.616708 0.442503 0.028 Uiso 1 1 calc R . . . .
C9 C 0.5179(2) 0.68545(17) 0.31504(18) 0.0244(4) Uani 1 1 d . . . . .
H9A H 0.566967 0.755301 0.377751 0.029 Uiso 1 1 calc R . . . .
H9B H 0.431343 0.720902 0.243740 0.029 Uiso 1 1 calc R . . . .
C10 C 0.6327(2) 0.62494(18) 0.23640(18) 0.0231(3) Uani 1 1 d . . . . .
H10A H 0.576352 0.585709 0.145965 0.028 Uiso 1 1 calc R . . . .
H10B H 0.696864 0.692765 0.211090 0.028 Uiso 1 1 calc R . . . .
C11 C 0.73414(17) 0.52442(17) 0.32591(16) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.74679(16) 0.52059(16) 0.49388(16) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.85916(17) 0.34743(16) 0.68191(17) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.82874(18) 0.40268(16) 0.80822(17) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.791023 0.486651 0.805639 0.023 Uiso 1 1 calc R . . . .
C15 C 0.85496(18) 0.33190(17) 0.93780(17) 0.0196(3) Uani 1 1 d . . . . .
H15 H 0.831829 0.368457 1.020576 0.024 Uiso 1 1 calc R . . . .
C16 C 0.91494(18) 0.20788(17) 0.94542(17) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.930487 0.160717 1.031934 0.025 Uiso 1 1 calc R . . . .
C17 C 0.95150(18) 0.15513(16) 0.82173(18) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.995369 0.073256 0.826498 0.025 Uiso 1 1 calc R . . . .
C18 C 0.92309(17) 0.22359(16) 0.69120(17) 0.0189(3) Uani 1 1 d . . . . .
H18 H 0.946868 0.186631 0.608925 0.023 Uiso 1 1 calc R . . . .
C19 C 0.40410(18) 0.63169(17) 0.77806(18) 0.0205(3) Uani 1 1 d . . . . .
C20 C 0.2118(2) 0.47311(19) 0.7089(2) 0.0280(4) Uani 1 1 d . . . . .
H20A H 0.183571 0.403826 0.639839 0.042 Uiso 1 1 calc GR . . . .
H20B H 0.131996 0.537220 0.691666 0.042 Uiso 1 1 calc GR . . . .
H20C H 0.225658 0.439914 0.806530 0.042 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
O1 C1 1.3824(18) . ?
O1 C12 1.4920(19) . ?
O2 H2 0.8200 . ?
O2 C4 1.3611(19) . ?
O3 C11 1.213(2) . ?
O4 C19 1.217(2) . ?
O5 C19 1.330(2) . ?
O5 C20 1.4518(19) . ?
N1 H1 0.8600 . ?
N1 C12 1.407(2) . ?
N1 C13 1.396(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.379(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.411(2) . ?
C5 C19 1.478(2) . ?
C6 C7 1.509(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.543(2) . ?
C7 C12 1.561(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.502(2) . ?
C11 C12 1.556(2) . ?
C13 C14 1.399(2) . ?
C13 C18 1.397(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C1 O1 C12 107.39(11) . . ?
C4 O2 H2 109.5 . . ?
C19 O5 C20 115.61(13) . . ?
C12 N1 H1 114.5 . . ?
C13 N1 H1 114.5 . . ?
C13 N1 C12 131.08(13) . . ?
O1 C1 C2 123.61(14) . . ?
C6 C1 O1 113.49(13) . . ?
C6 C1 C2 122.83(14) . . ?
C1 C2 H2A 121.1 . . ?
C1 C2 C3 117.82(15) . . ?
C3 C2 H2A 121.1 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(15) . . ?
C4 C3 H3 119.4 . . ?
O2 C4 C3 116.63(14) . . ?
O2 C4 C5 122.73(15) . . ?
C3 C4 C5 120.64(14) . . ?
C4 C5 C19 118.33(13) . . ?
C6 C5 C4 117.71(14) . . ?
C6 C5 C19 123.93(14) . . ?
C1 C6 C5 119.82(14) . . ?
C1 C6 C7 108.45(13) . . ?
C5 C6 C7 131.71(14) . . ?
C6 C7 H7 110.5 . . ?
C6 C7 C8 110.95(13) . . ?
C6 C7 C12 102.46(12) . . ?
C8 C7 H7 110.5 . . ?
C8 C7 C12 111.83(12) . . ?
C12 C7 H7 110.5 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.71(13) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.45(14) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.47(13) . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
O3 C11 C10 122.00(14) . . ?
O3 C11 C12 119.50(14) . . ?
C10 C11 C12 118.51(14) . . ?
O1 C12 C7 104.56(11) . . ?
O1 C12 C11 102.23(12) . . ?
N1 C12 O1 112.21(12) . . ?
N1 C12 C7 116.81(13) . . ?
N1 C12 C11 106.14(13) . . ?
C11 C12 C7 114.06(12) . . ?
N1 C13 C14 124.32(15) . . ?
N1 C13 C18 117.07(14) . . ?
C18 C13 C14 118.61(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.99(15) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.08(15) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.93(15) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.54(15) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.76(14) . . ?
C17 C18 H18 119.6 . . ?
O4 C19 O5 122.41(15) . . ?
O4 C19 C5 123.46(15) . . ?
O5 C19 C5 114.12(13) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C1 C2 C3 -176.20(14) . . . . ?
O1 C1 C6 C5 175.60(13) . . . . ?
O1 C1 C6 C7 -3.30(18) . . . . ?
O2 C4 C5 C6 179.02(14) . . . . ?
O2 C4 C5 C19 -2.9(2) . . . . ?
O3 C11 C12 O1 109.67(16) . . . . ?
O3 C11 C12 N1 -8.1(2) . . . . ?
O3 C11 C12 C7 -138.10(15) . . . . ?
N1 C13 C14 C15 177.23(15) . . . . ?
N1 C13 C18 C17 -178.47(14) . . . . ?
C1 O1 C12 N1 -110.10(13) . . . . ?
C1 O1 C12 C7 17.44(14) . . . . ?
C1 O1 C12 C11 136.60(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C6 C7 C8 -105.79(14) . . . . ?
C1 C6 C7 C12 13.71(16) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 C6 C7 179.64(14) . . . . ?
C2 C3 C4 O2 -179.91(14) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C4 C5 C19 177.51(15) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C4 C5 C6 C7 -179.97(15) . . . . ?
C4 C5 C19 O4 2.8(2) . . . . ?
C4 C5 C19 O5 -176.49(14) . . . . ?
C5 C6 C7 C8 75.5(2) . . . . ?
C5 C6 C7 C12 -165.02(16) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C6 C5 C19 O4 -179.26(16) . . . . ?
C6 C5 C19 O5 1.5(2) . . . . ?
C6 C7 C8 C9 71.00(17) . . . . ?
C6 C7 C12 O1 -18.49(14) . . . . ?
C6 C7 C12 N1 106.18(15) . . . . ?
C6 C7 C12 C11 -129.31(14) . . . . ?
C7 C8 C9 C10 68.93(17) . . . . ?
C8 C7 C12 O1 100.39(14) . . . . ?
C8 C7 C12 N1 -134.95(15) . . . . ?
C8 C7 C12 C11 -10.44(19) . . . . ?
C8 C9 C10 C11 -36.40(19) . . . . ?
C9 C10 C11 O3 163.19(15) . . . . ?
C9 C10 C11 C12 -17.1(2) . . . . ?
C10 C11 C12 O1 -70.00(16) . . . . ?
C10 C11 C12 N1 172.27(14) . . . . ?
C10 C11 C12 C7 42.2(2) . . . . ?
C12 O1 C1 C2 167.62(14) . . . . ?
C12 O1 C1 C6 -9.40(17) . . . . ?
C12 N1 C13 C14 -12.1(3) . . . . ?
C12 N1 C13 C18 168.33(16) . . . . ?
C12 C7 C8 C9 -42.72(18) . . . . ?
C13 N1 C12 O1 78.8(2) . . . . ?
C13 N1 C12 C7 -41.9(2) . . . . ?
C13 N1 C12 C11 -170.34(15) . . . . ?
C13 C14 C15 C16 1.7(2) . . . . ?
C14 C13 C18 C17 2.0(2) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C18 -2.4(2) . . . . ?
C16 C17 C18 C13 0.9(2) . . . . ?
C18 C13 C14 C15 -3.2(2) . . . . ?
C19 C5 C6 C1 -176.56(14) . . . . ?
C19 C5 C6 C7 2.0(3) . . . . ?
C20 O5 C19 O4 1.3(2) . . . . ?
C20 O5 C19 C5 -179.49(14) . . . . ?

_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.876
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_str0268lt100kcu
_database_code_depnum_ccdc_archive 'CCDC 1921254'
loop_
_audit_author_name
_audit_author_address
'Vladimir N. Nesterov'
;University of North Texas
United States of America
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 O6'
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H10O6
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'
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                   7.17307(3)
_cell_length_b                   9.46902(5)
_cell_length_c                   36.9162(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2507.42(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    37812
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4330
_cell_measurement_theta_min      3.6050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84005
_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_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            52023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.474
_diffrn_reflns_theta_min         4.792
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00 116.00   0.50    0.50    --   39.20  57.00  60.00  210
  2  ω    102.00 178.00   0.50    0.50    --  116.00 104.00 140.00  152
  3  ω     99.00 178.00   0.50    0.50    --  116.00 111.00 120.00  158
  4  ω     85.00 178.00   0.50    0.50    --  116.00  77.00  30.00  186
  5  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-120.00  158
  6  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-180.00  158
  7  ω     99.00 178.00   0.50    0.50    --  116.00 111.00-150.00  158
  8  ω     85.00 178.00   0.50    0.50    --  116.00  77.00-150.00  186
  9  ω     86.00 178.00   0.50    0.50    --  116.00  45.00 -90.00  184
 10  ω     86.00 178.00   0.50    0.50    --  116.00  61.00  90.00  184
 11  ω     78.00 178.00   0.50    0.50    --  116.00  30.00-120.00  200
 12  ω     86.00 178.00   0.50    0.50    --  116.00  45.00-180.00  184
 13  ω     85.00 178.00   0.50    0.50    --  116.00  77.00-180.00  186
 14  ω     59.00 150.00   0.50    0.50    --  116.00 178.00 -90.00  182
 15  ω     59.00 150.00   0.50    0.50    --  116.00 178.00  60.00  182
 16  ω     35.00 178.00   0.50    0.50    --  116.00  15.00  30.00  286
 17  ω     35.00 111.00   0.50    0.50    --  116.00-104.00  39.00  152
 18  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00  60.00  110
 19  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00 150.00  148
 20  ω     35.00 112.00   0.50    0.50    --  116.00-111.00  90.00  154
 21  ω     35.00 112.00   0.50    0.50    --  116.00-111.00   0.00  154
 22  ω     30.00 100.00   0.50    0.50    --   39.20-125.00 -90.00  140
 23  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00-150.00  110
 24  ω     41.00  96.00   0.50    0.50    --  116.00 -77.00-180.00  110
 25  ω     35.00 112.00   0.50    0.50    --  116.00-111.00-120.00  154
 26  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00-120.00  148
 27  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 -30.00  154
 28  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00-180.00  148
 29  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 -60.00  154
 30  ω     35.00 109.00   0.50    0.50    --  116.00 -94.00  60.00  148
 31  ω     35.00 112.00   0.50    0.50    --  116.00-111.00 150.00  154
 32  ω     13.00  88.00   0.50    0.50    --   39.20-104.00  39.00  150
 33  ω     11.00 116.00   0.50    0.50    --   39.20  57.00-180.00  210
 34  ω      4.00  41.00   0.50    0.50    --   39.20  77.00-120.00   74
 35  ω      4.00  41.00   0.50    0.50    --   39.20  77.00-180.00   74
 36  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -90.00   74
 37  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -30.00   74
 38  ω      4.00  41.00   0.50    0.50    --   39.20  77.00   0.00   74
 39  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  60.00   74
 40  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  30.00   74
 41  ω      4.00  41.00   0.50    0.50    --   39.20  77.00  90.00   74
 42  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 150.00   74
 43  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  60.00  124
 44  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  30.00  124
 45  ω    -46.00  16.00   0.50    0.50    --   39.20 -19.00  90.00  124
 46  ω    -67.00  37.00   0.50    0.50    --  -39.20  57.00  30.00  208
 47  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 -30.00   68
 48  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00   0.00   68
 49  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 -90.00   68
 50  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00-180.00   68
 51  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00-150.00   80
 52  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00-180.00   80
 53  ω   -176.00 -80.00   0.50    0.50    --  -94.50-104.00  39.00  192
 54  ω   -118.00 -78.00   0.50    0.50    --  -39.20-125.00  90.00   80
 55  ω   -171.00 -64.00   0.50    0.50    --  -94.50 -61.00 120.00  214
 56  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 150.00   68
 57  ω    -45.00 -11.00   0.50    0.50    --  -94.50  30.00 120.00   68
 58  ω    -86.00   8.00   0.50    0.50    --  -39.20 104.00 140.00  188
 59  ω      4.00  41.00   0.50    0.50    --   39.20  77.00 -60.00   74
 60  ω    -85.00 -13.00   0.50    0.50    --  -94.50 104.00 140.00  144
;
_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      -0.0168024000
_diffrn_orient_matrix_UB_12      -0.0008488000
_diffrn_orient_matrix_UB_13      0.0416136000
_diffrn_orient_matrix_UB_21      0.0584828000
_diffrn_orient_matrix_UB_22      -0.1565022000
_diffrn_orient_matrix_UB_23      0.0006755000
_diffrn_orient_matrix_UB_31      0.2059133000
_diffrn_orient_matrix_UB_32      0.0444454000
_diffrn_orient_matrix_UB_33      0.0032064000
_diffrn_oxdiff_ac3_digest_frames 
;
01fa6e92c5b04c14b45882ea8dceb65f8e000578c83
;
_diffrn_oxdiff_ac3_digest_hkl    
;
013fa937a9e11914ff5eedb4a72c19eba11306
;
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5059
_reflns_number_total             5118
_reflns_odcompleteness_completeness 99.96
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.848
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 2120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.00095(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.054
_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)+(0.0427P)²+0.8631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4A) = Uanis(C5A) = Uanis(C4B) = Uanis(C5B)
3. Rigid body (RIGU) restrains
 C6A, C5A, C4A, C3A, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6A, C5B, C4B, C3A, C2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(H3AC)=Sof(H3AD)=Sof(H6AB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=
 Sof(H5BB)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=
 Sof(H6AA)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6A(H6AA), C6A(H6AB), C6(H6B)
5.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C3A(H3AC,H3AD), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C3(H3A,H3B),
 C4(H4A,H4B), C5(H5A,H5B), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
5.c Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C11A(H11A), C10(H10), C11(H11)
5.d Idealised Me refined as rotating group:
 C14A(H14A,H14B,H14C), C14(H14D,H14E,H14F)
5.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O6A(H6A), O2(H2), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_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 0.6214(2) 0.35649(15) 0.28133(4) 0.0225(3) Uani 1 1 d . . . . .
O1A O 0.2518(2) 0.42898(15) 0.42716(4) 0.0262(3) Uani 1 1 d . . . . .
O2A O 0.5025(2) 0.54263(16) 0.45449(4) 0.0272(3) Uani 1 1 d . . . . .
H2A H 0.553709 0.465424 0.455957 0.041 Uiso 1 1 calc GR . . . .
O3A O 0.3582(3) 0.37861(17) 0.50730(4) 0.0346(4) Uani 1 1 d . . . . .
O4A O 0.0589(2) 0.98814(18) 0.36362(4) 0.0304(4) Uani 1 1 d . . . . .
O5A O 0.1809(2) 0.94686(16) 0.41854(4) 0.0276(3) Uani 1 1 d . . . . .
O6A O 0.0516(2) 0.78438(19) 0.31665(4) 0.0308(4) Uani 1 1 d . . . . .
H6A H 0.034118 0.864829 0.324139 0.046 Uiso 1 1 calc GR . . . .
C1A C 0.3120(3) 0.5248(2) 0.45556(5) 0.0253(4) Uani 1 1 d . . . . .
C2A C 0.2466(3) 0.4466(2) 0.48994(5) 0.0270(4) Uani 1 1 d . U . . .
C3A C 0.0429(3) 0.4553(3) 0.49900(6) 0.0305(5) Uani 1 1 d . U . . .
H3AA H 0.029268 0.480430 0.524337 0.037 Uiso 0.807(5) 1 calc R . P A 1
H3AB H -0.013430 0.363223 0.495513 0.037 Uiso 0.807(5) 1 calc R . P A 1
H3AC H -0.027441 0.403647 0.480899 0.037 Uiso 0.193(5) 1 calc R . P A 2
H3AD H 0.021758 0.410226 0.522228 0.037 Uiso 0.193(5) 1 calc R . P A 2
C4A C -0.0620(4) 0.5651(3) 0.47550(8) 0.0307(5) Uani 0.807(5) 1 d . U P A 1
H4AA H -0.090190 0.522740 0.452214 0.037 Uiso 0.807(5) 1 calc R . P A 1
H4AB H -0.179563 0.587427 0.487162 0.037 Uiso 0.807(5) 1 calc R . P A 1
C5A C 0.0391(5) 0.6948(5) 0.46947(12) 0.0307(5) Uani 0.807(5) 1 d . U P A 1
H5AA H 0.070434 0.736914 0.492635 0.037 Uiso 0.807(5) 1 calc R . P A 1
H5AB H -0.039885 0.760682 0.456448 0.037 Uiso 0.807(5) 1 calc R . P A 1
C6A C 0.2200(3) 0.6695(2) 0.44755(5) 0.0269(5) Uani 1 1 d . U . . .
H6AA H 0.309010 0.746196 0.451884 0.032 Uiso 0.807(5) 1 calc R . P A 1
H6AB H 0.319453 0.739947 0.449769 0.032 Uiso 0.193(5) 1 calc R . P A 2
C7A C 0.1831(3) 0.6536(2) 0.40716(5) 0.0218(4) Uani 1 1 d . . . . .
C8A C 0.1326(3) 0.7515(2) 0.38020(5) 0.0229(4) Uani 1 1 d . . . . .
C9A C 0.1021(3) 0.6991(3) 0.34482(5) 0.0254(4) Uani 1 1 d . . . . .
C10A C 0.1226(3) 0.5558(3) 0.33703(6) 0.0292(5) Uani 1 1 d . . . . .
H10A H 0.102563 0.523785 0.313530 0.035 Uiso 1 1 calc R . . . .
C11A C 0.1723(3) 0.4608(2) 0.36369(6) 0.0280(5) Uani 1 1 d . . . . .
H11A H 0.185160 0.365026 0.358655 0.034 Uiso 1 1 calc R . . . .
C12A C 0.2023(3) 0.5134(2) 0.39824(5) 0.0239(4) Uani 1 1 d . . . . .
C13A C 0.1191(3) 0.9054(2) 0.38636(6) 0.0240(4) Uani 1 1 d . . . . .
C14A C 0.1771(4) 1.0983(2) 0.42532(7) 0.0320(5) Uani 1 1 d . . . . .
H14A H 0.271744 1.143710 0.411094 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.199881 1.115799 0.450554 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.057103 1.135348 0.418796 0.048 Uiso 1 1 calc GR . . . .
O2 O 0.8003(2) 0.18090(17) 0.25387(4) 0.0263(3) Uani 1 1 d . . . . .
H2 H 0.813112 0.219352 0.234123 0.039 Uiso 1 1 calc GR . . . .
O3 O 0.5256(2) 0.21921(17) 0.20636(4) 0.0273(3) Uani 1 1 d . . . . .
O4 O 0.7009(2) 0.02647(15) 0.41762(4) 0.0238(3) Uani 1 1 d . . . . .
O5 O 0.6073(2) -0.05451(14) 0.36370(4) 0.0218(3) Uani 1 1 d . . . . .
O6 O 0.7140(2) 0.29922(14) 0.42820(3) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.716181 0.215908 0.434248 0.034 Uiso 1 1 calc GR . . . .
C1 C 0.6266(3) 0.2121(2) 0.26762(5) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.4765(3) 0.2163(2) 0.23769(5) 0.0224(4) Uani 1 1 d . . . . .
C3 C 0.2755(3) 0.2217(3) 0.24937(6) 0.0301(5) Uani 1 1 d . . . . .
H3A H 0.205149 0.152846 0.235536 0.036 Uiso 1 1 calc R . . . .
H3B H 0.225490 0.314410 0.243842 0.036 Uiso 1 1 calc R . . . .
C4 C 0.2488(3) 0.1921(2) 0.28978(5) 0.0265(4) Uani 1 1 d . . . . .
H4A H 0.277605 0.276227 0.303675 0.032 Uiso 1 1 calc R . . . .
H4B H 0.120068 0.166593 0.294451 0.032 Uiso 1 1 calc R . . . .
C5 C 0.3769(3) 0.0717(2) 0.30129(5) 0.0248(4) Uani 1 1 d . . . . .
H5A H 0.358608 -0.008008 0.285183 0.030 Uiso 1 1 calc R . . . .
H5B H 0.344049 0.041885 0.325603 0.030 Uiso 1 1 calc R . . . .
C6 C 0.5841(3) 0.1158(2) 0.30053(5) 0.0194(4) Uani 1 1 d . . . . .
H6B H 0.665231 0.032502 0.300467 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6323(3) 0.2130(2) 0.33181(5) 0.0184(4) Uani 1 1 d . . . . .
C8 C 0.6569(3) 0.1897(2) 0.36929(5) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.6881(3) 0.3084(2) 0.39161(5) 0.0191(4) Uani 1 1 d . . . . .
C10 C 0.6936(3) 0.4439(2) 0.37689(5) 0.0214(4) Uani 1 1 d . . . . .
H10 H 0.711711 0.521001 0.392087 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6726(3) 0.4656(2) 0.34010(5) 0.0219(4) Uani 1 1 d . . . . .
H11 H 0.677536 0.555910 0.330232 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6440(3) 0.3481(2) 0.31846(5) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.6580(3) 0.0482(2) 0.38605(5) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.6115(3) -0.1956(2) 0.37872(6) 0.0228(4) Uani 1 1 d . . . . .
H14D H 0.547832 -0.259257 0.362696 0.034 Uiso 1 1 calc GR . . . .
H14E H 0.550871 -0.195749 0.401909 0.034 Uiso 1 1 calc GR . . . .
H14F H 0.738562 -0.225509 0.381536 0.034 Uiso 1 1 calc GR . . . .
C4B C -0.0218(18) 0.5910(13) 0.5005(3) 0.0307(5) Uani 0.193(5) 1 d . U P A 2
H4BA H -0.007998 0.624324 0.525191 0.037 Uiso 0.193(5) 1 calc R . P A 2
H4BB H -0.154222 0.589290 0.495161 0.037 Uiso 0.193(5) 1 calc R . P A 2
C5B C 0.079(2) 0.711(2) 0.4727(5) 0.0307(5) Uani 0.193(5) 1 d . U P A 2
H5BA H -0.019794 0.754691 0.458897 0.037 Uiso 0.193(5) 1 calc R . P A 2
H5BB H 0.132706 0.783397 0.487999 0.037 Uiso 0.193(5) 1 calc R . 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 C1 1.459(2) . ?
O1 C12 1.382(2) . ?
O1A C1A 1.453(3) . ?
O1A C12A 1.380(2) . ?
O2A H2A 0.8200 . ?
O2A C1A 1.377(3) . ?
O3A C2A 1.211(3) . ?
O4A C13A 1.227(3) . ?
O5A C13A 1.327(3) . ?
O5A C14A 1.456(3) . ?
O6A H6A 0.8200 . ?
O6A C9A 1.366(2) . ?
C1A C2A 1.542(3) . ?
C1A C6A 1.550(3) . ?
C2A C3A 1.501(3) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A H3AC 0.9700 . ?
C3A H3AD 0.9700 . ?
C3A C4A 1.549(4) . ?
C3A C4B 1.367(12) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.443(5) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.548(5) . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A C7A 1.522(3) . ?
C6A C5B 1.426(19) . ?
C7A C8A 1.408(3) . ?
C7A C12A 1.375(3) . ?
C8A C9A 1.414(3) . ?
C8A C13A 1.478(3) . ?
C9A C10A 1.395(3) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.380(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.386(3) . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
O2 H2 0.8200 . ?
O2 C1 1.378(2) . ?
O3 C2 1.209(2) . ?
O4 C13 1.223(2) . ?
O5 C13 1.326(2) . ?
O5 C14 1.447(2) . ?
O6 H6 0.8200 . ?
O6 C9 1.366(2) . ?
C1 C2 1.543(3) . ?
C1 C6 1.550(3) . ?
C2 C3 1.505(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.530(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.524(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.544(3) . ?
C6 H6B 0.9800 . ?
C6 C7 1.517(3) . ?
C7 C8 1.412(2) . ?
C7 C12 1.374(3) . ?
C8 C9 1.411(3) . ?
C8 C13 1.476(3) . ?
C9 C10 1.394(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.69(2) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?

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
C12 O1 C1 106.71(14) . . ?
C12A O1A C1A 105.86(15) . . ?
C1A O2A H2A 109.5 . . ?
C13A O5A C14A 116.05(17) . . ?
C9A O6A H6A 109.5 . . ?
O1A C1A C2A 101.76(16) . . ?
O1A C1A C6A 106.73(17) . . ?
O2A C1A O1A 110.54(17) . . ?
O2A C1A C2A 112.61(18) . . ?
O2A C1A C6A 107.99(18) . . ?
C2A C1A C6A 116.85(17) . . ?
O3A C2A C1A 119.3(2) . . ?
O3A C2A C3A 123.7(2) . . ?
C3A C2A C1A 116.96(18) . . ?
C2A C3A H3AA 109.1 . . ?
C2A C3A H3AB 109.1 . . ?
C2A C3A H3AC 109.0 . . ?
C2A C3A H3AD 109.0 . . ?
C2A C3A C4A 112.64(19) . . ?
H3AA C3A H3AB 107.8 . . ?
H3AC C3A H3AD 107.8 . . ?
C4A C3A H3AA 109.1 . . ?
C4A C3A H3AB 109.1 . . ?
C4B C3A C2A 113.0(6) . . ?
C4B C3A H3AC 109.0 . . ?
C4B C3A H3AD 109.0 . . ?
C3A C4A H4AA 108.7 . . ?
C3A C4A H4AB 108.7 . . ?
H4AA C4A H4AB 107.6 . . ?
C5A C4A C3A 114.4(3) . . ?
C5A C4A H4AA 108.7 . . ?
C5A C4A H4AB 108.7 . . ?
C4A C5A H5AA 109.3 . . ?
C4A C5A H5AB 109.3 . . ?
C4A C5A C6A 111.7(3) . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A H5AA 109.3 . . ?
C6A C5A H5AB 109.3 . . ?
C1A C6A H6AA 110.3 . . ?
C1A C6A H6AB 106.0 . . ?
C5A C6A C1A 113.2(2) . . ?
C5A C6A H6AA 110.3 . . ?
C7A C6A C1A 99.99(16) . . ?
C7A C6A C5A 112.4(2) . . ?
C7A C6A H6AA 110.3 . . ?
C7A C6A H6AB 106.0 . . ?
C5B C6A C1A 114.7(9) . . ?
C5B C6A H6AB 106.0 . . ?
C5B C6A C7A 122.9(8) . . ?
C8A C7A C6A 132.26(19) . . ?
C12A C7A C6A 108.23(18) . . ?
C12A C7A C8A 119.50(19) . . ?
C7A C8A C9A 117.5(2) . . ?
C7A C8A C13A 123.86(19) . . ?
C9A C8A C13A 118.57(19) . . ?
O6A C9A C8A 122.5(2) . . ?
O6A C9A C10A 116.50(19) . . ?
C10A C9A C8A 121.04(19) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A C9A 120.95(19) . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A H11A 121.2 . . ?
C10A C11A C12A 117.5(2) . . ?
C12A C11A H11A 121.2 . . ?
O1A C12A C11A 122.94(19) . . ?
C7A C12A O1A 113.57(18) . . ?
C7A C12A C11A 123.5(2) . . ?
O4A C13A O5A 122.7(2) . . ?
O4A C13A C8A 123.2(2) . . ?
O5A C13A C8A 114.06(17) . . ?
O5A C14A H14A 109.5 . . ?
O5A C14A H14B 109.5 . . ?
O5A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C13 O5 C14 115.65(15) . . ?
C9 O6 H6 109.5 . . ?
O1 C1 C2 101.90(15) . . ?
O1 C1 C6 105.94(14) . . ?
O2 C1 O1 110.59(16) . . ?
O2 C1 C2 111.90(15) . . ?
O2 C1 C6 109.92(16) . . ?
C2 C1 C6 116.07(17) . . ?
O3 C2 C1 118.82(19) . . ?
O3 C2 C3 123.51(19) . . ?
C3 C2 C1 117.63(16) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 113.14(17) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.49(17) . . ?
C5 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 111.92(17) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C1 C6 H6B 110.8 . . ?
C5 C6 C1 111.26(16) . . ?
C5 C6 H6B 110.8 . . ?
C7 C6 C1 101.25(15) . . ?
C7 C6 C5 111.69(16) . . ?
C7 C6 H6B 110.8 . . ?
C8 C7 C6 132.84(18) . . ?
C12 C7 C6 107.82(16) . . ?
C12 C7 C8 119.27(17) . . ?
C7 C8 C13 123.56(17) . . ?
C9 C8 C7 117.88(17) . . ?
C9 C8 C13 118.52(16) . . ?
O6 C9 C8 123.21(17) . . ?
O6 C9 C10 116.13(17) . . ?
C10 C9 C8 120.66(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.15(18) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 121.2 . . ?
C10 C11 C12 117.61(18) . . ?
C12 C11 H11 121.2 . . ?
O1 C12 C11 122.92(17) . . ?
C7 C12 O1 113.69(17) . . ?
C7 C12 C11 123.39(17) . . ?
O4 C13 O5 122.59(18) . . ?
O4 C13 C8 123.62(18) . . ?
O5 C13 C8 113.79(16) . . ?
O5 C14 H14D 109.5 . . ?
O5 C14 H14E 109.5 . . ?
O5 C14 H14F 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C3A C4B H4BA 108.0 . . ?
C3A C4B H4BB 108.0 . . ?
C3A C4B C5B 117.3(10) . . ?
H4BA C4B H4BB 107.2 . . ?
C5B C4B H4BA 108.0 . . ?
C5B C4B H4BB 108.0 . . ?
C6A C5B C4B 121.1(14) . . ?
C6A C5B H5BA 107.0 . . ?
C6A C5B H5BB 107.0 . . ?
C4B C5B H5BA 107.0 . . ?
C4B C5B H5BB 107.0 . . ?
H5BA C5B H5BB 106.8 . . ?

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 O3 104.8(2) . . . . ?
O1 C1 C2 C3 -73.2(2) . . . . ?
O1 C1 C6 C5 97.88(18) . . . . ?
O1 C1 C6 C7 -20.92(19) . . . . ?
O1A C1A C2A O3A 99.9(2) . . . . ?
O1A C1A C2A C3A -77.6(2) . . . . ?
O1A C1A C6A C5A 97.3(2) . . . . ?
O1A C1A C6A C7A -22.6(2) . . . . ?
O1A C1A C6A C5B 110.9(8) . . . . ?
O2A C1A C2A O3A -18.5(3) . . . . ?
O2A C1A C2A C3A 163.99(19) . . . . ?
O2A C1A C6A C5A -143.9(2) . . . . ?
O2A C1A C6A C7A 96.30(19) . . . . ?
O2A C1A C6A C5B -130.3(8) . . . . ?
O3A C2A C3A C4A 172.3(2) . . . . ?
O3A C2A C3A C4B 129.4(6) . . . . ?
O6A C9A C10A C11A -179.6(2) . . . . ?
C1A O1A C12A C7A -14.0(2) . . . . ?
C1A O1A C12A C11A 167.0(2) . . . . ?
C1A C2A C3A C4A -10.3(3) . . . . ?
C1A C2A C3A C4B -53.2(6) . . . . ?
C1A C6A C7A C8A -167.0(2) . . . . ?
C1A C6A C7A C12A 14.6(2) . . . . ?
C1A C6A C5B C4B -17.7(15) . . . . ?
C2A C1A C6A C5A -15.7(3) . . . . ?
C2A C1A C6A C7A -135.57(19) . . . . ?
C2A C1A C6A C5B -2.1(8) . . . . ?
C2A C3A C4A C5A -40.9(3) . . . . ?
C2A C3A C4B C5B 31.7(12) . . . . ?
C3A C4A C5A C6A 64.0(4) . . . . ?
C3A C4B C5B C6A 3.0(19) . . . . ?
C4A C5A C6A C1A -33.3(4) . . . . ?
C4A C5A C6A C7A 79.1(3) . . . . ?
C5A C6A C7A C8A 72.6(3) . . . . ?
C5A C6A C7A C12A -105.8(3) . . . . ?
C6A C1A C2A O3A -144.3(2) . . . . ?
C6A C1A C2A C3A 38.1(3) . . . . ?
C6A C7A C8A C9A -177.7(2) . . . . ?
C6A C7A C8A C13A 5.5(4) . . . . ?
C6A C7A C12A O1A -1.2(2) . . . . ?
C6A C7A C12A C11A 177.8(2) . . . . ?
C7A C6A C5B C4B 103.9(13) . . . . ?
C7A C8A C9A O6A 179.61(19) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C7A C8A C13A O4A -173.2(2) . . . . ?
C7A C8A C13A O5A 7.9(3) . . . . ?
C8A C7A C12A O1A -179.88(18) . . . . ?
C8A C7A C12A C11A -0.8(3) . . . . ?
C8A C9A C10A C11A 0.4(3) . . . . ?
C9A C8A C13A O4A 9.9(3) . . . . ?
C9A C8A C13A O5A -168.92(18) . . . . ?
C9A C10A C11A C12A -0.5(3) . . . . ?
C10A C11A C12A O1A 179.74(19) . . . . ?
C10A C11A C12A C7A 0.8(3) . . . . ?
C12A O1A C1A O2A -94.20(19) . . . . ?
C12A O1A C1A C2A 145.97(16) . . . . ?
C12A O1A C1A C6A 23.0(2) . . . . ?
C12A C7A C8A C9A 0.6(3) . . . . ?
C12A C7A C8A C13A -176.27(19) . . . . ?
C13A C8A C9A O6A -3.4(3) . . . . ?
C13A C8A C9A C10A 176.64(19) . . . . ?
C14A O5A C13A O4A -1.1(3) . . . . ?
C14A O5A C13A C8A 177.69(18) . . . . ?
O2 C1 C2 O3 -13.4(3) . . . . ?
O2 C1 C2 C3 168.67(19) . . . . ?
O2 C1 C6 C5 -142.61(16) . . . . ?
O2 C1 C6 C7 98.59(17) . . . . ?
O3 C2 C3 C4 170.5(2) . . . . ?
O6 C9 C10 C11 178.78(18) . . . . ?
C1 O1 C12 C7 -10.4(2) . . . . ?
C1 O1 C12 C11 170.60(18) . . . . ?
C1 C2 C3 C4 -11.7(3) . . . . ?
C1 C6 C7 C8 -167.8(2) . . . . ?
C1 C6 C7 C12 15.2(2) . . . . ?
C2 C1 C6 C5 -14.4(2) . . . . ?
C2 C1 C6 C7 -133.16(17) . . . . ?
C2 C3 C4 C5 -41.1(3) . . . . ?
C3 C4 C5 C6 69.1(2) . . . . ?
C4 C5 C6 C1 -38.6(2) . . . . ?
C4 C5 C6 C7 73.7(2) . . . . ?
C5 C6 C7 C8 73.7(3) . . . . ?
C5 C6 C7 C12 -103.31(19) . . . . ?
C6 C1 C2 O3 -140.66(19) . . . . ?
C6 C1 C2 C3 41.4(3) . . . . ?
C6 C7 C8 C9 -175.2(2) . . . . ?
C6 C7 C8 C13 7.0(3) . . . . ?
C6 C7 C12 O1 -3.8(2) . . . . ?
C6 C7 C12 C11 175.19(18) . . . . ?
C7 C8 C9 O6 -179.91(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C13 O4 171.04(19) . . . . ?
C7 C8 C13 O5 -9.2(3) . . . . ?
C8 C7 C12 O1 178.68(17) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C9 C8 C13 O4 -6.8(3) . . . . ?
C9 C8 C13 O5 172.98(18) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 O1 -179.89(19) . . . . ?
C10 C11 C12 C7 1.2(3) . . . . ?
C12 O1 C1 O2 -99.36(17) . . . . ?
C12 O1 C1 C2 141.53(16) . . . . ?
C12 O1 C1 C6 19.7(2) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C12 C7 C8 C13 -176.28(18) . . . . ?
C13 C8 C9 O6 -2.0(3) . . . . ?
C13 C8 C9 C10 178.15(18) . . . . ?
C14 O5 C13 O4 -1.9(3) . . . . ?
C14 O5 C13 C8 178.34(16) . . . . ?
C5B C6A C7A C8A 64.7(10) . . . . ?
C5B C6A C7A C12A -113.7(10) . . . . ?

_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.797
_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_str0214lt100kcu
_database_code_depnum_ccdc_archive 'CCDC 1919286'
loop_
_audit_author_name
_audit_author_address
'Vladimir N. Nesterov'
;Department of Chemistry, University of North Texas
United States of America
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2020-07-08 downloaded from the CCDC.
;
_audit_creation_date             2019-02-14
_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        ?
_chemical_formula_moiety         'C20 H17 N O4'
_chemical_formula_sum            'C20 H17 N O4'
_chemical_formula_weight         335.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H17NO5
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                   12.27300(10)
_cell_length_b                   13.85930(10)
_cell_length_c                   19.0331(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.9840(10)
_cell_angle_gamma                90
_cell_volume                     3141.49(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21175
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.1770
_cell_measurement_theta_min      3.7150
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29255
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.708
_diffrn_reflns_theta_min         3.712
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -46.00   0.50    0.50    --  -47.07 -32.00  10.00  150
  2  ω    -41.00  16.00   0.50    0.50    --  -47.07  32.00 169.00  114
  3  ω     53.00  78.00   0.50    0.50    --   47.07  32.00 169.00   50
  4  ω    -25.00   0.00   0.50    0.50    --   47.07 -32.00  10.00   50
  5  ω   -141.00-116.00   0.50    0.50    --  -86.25 -32.00  10.00   50
  6  ω    -47.00 -22.00   0.50    0.50    --  -86.25  32.00 169.00   50
  7  ω     95.00 173.00   0.50    0.50    --  107.75  32.00 169.00  156
  8  ω   -119.00 -79.00   0.50    0.50    --  -47.07-125.00-180.00   80
  9  ω    -27.00  14.00   0.50    0.50    --   47.07 -19.00-150.00   82
 10  ω     85.00 119.00   0.50    0.50    --   47.07  77.00 -30.00   68
 11  ω    -26.00  15.00   0.50    0.50    --   47.07 -19.00 -90.00   82
 12  ω     88.00 118.00   0.50    0.50    --   47.07  77.00-120.00   60
 13  ω    -59.00 -24.00   0.50    0.50    --  -86.25  45.00   0.00   70
 14  ω    -45.00 -20.00   0.50    0.50    --  -86.25  30.00 -30.00   50
 15  ω     34.00  59.00   0.50    0.50    --  107.75 -61.00  90.00   50
 16  ω     54.00  95.00   0.50    0.50    --  107.75 -77.00-150.00   82
 17  ω     34.00  59.00   0.50    0.50    --  107.75 -61.00  60.00   50
 18  ω     34.00  60.00   0.50    0.50    --  107.75 -61.00   0.00   52
 19  ω     60.00  95.00   0.50    0.50    --  107.75 -77.00-120.00   70
 20  ω     34.00  61.00   0.50    0.50    --  107.75 -61.00 -30.00   54
 21  ω     39.00  91.00   0.50    0.50    --  107.75 -77.00  60.00  104
 22  ω     44.00  69.00   0.50    0.50    --  107.75 -77.00  90.00   50
 23  ω     98.00 155.00   0.50    0.50    --  107.75 125.00  60.00  114
 24  ω     37.00  94.00   0.50    0.50    --  107.75 -77.00   0.00  114
 25  ω    105.00 172.00   0.50    0.50    --  107.75 125.00  90.00  134
 26  ω    142.00 177.00   0.50    0.50    --  107.75  45.00 -90.00   70
 27  ω     94.00 135.00   0.50    0.50    --  107.75  45.00 -90.00   82
 28  ω    120.00 173.00   0.50    0.50    --  107.75  15.00  30.00  106
 29  ω     42.00  73.00   0.50    0.50    --  107.75-125.00 -30.00   62
 30  ω     84.00 110.00   0.50    0.50    --  107.75-125.00 -30.00   52
 31  ω     64.00  90.00   0.50    0.50    --  107.75 -77.00  30.00   52
 32  ω     48.00  96.00   0.50    0.50    --  107.75 -77.00 150.00   96
 33  ω     34.00  59.00   0.50    0.50    --  107.75 -61.00  30.00   50
 34  ω     34.00  59.00   0.50    0.50    --  107.75 -61.00 -90.00   50
 35  ω     95.00 145.00   0.50    0.50    --  107.75  45.00-150.00  100
 36  ω     36.00  61.00   0.50    0.50    --  107.75 -61.00-150.00   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      -0.0213243000
_diffrn_orient_matrix_UB_12      -0.0002368000
_diffrn_orient_matrix_UB_13      0.0765087000
_diffrn_orient_matrix_UB_21      0.1161531000
_diffrn_orient_matrix_UB_22      -0.0459255000
_diffrn_orient_matrix_UB_23      0.0301985000
_diffrn_orient_matrix_UB_31      0.0527282000
_diffrn_orient_matrix_UB_32      0.1012546000
_diffrn_orient_matrix_UB_33      0.0138607000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6030
_reflns_number_total             6612
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.045
_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)+(0.0561P)²+1.2199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C10A(H10C,H10D), C11A(H11C,
 H11D), C12A(H12C,H12D)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C4A(H4A),
 C5A(H5A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_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 0.55080(8) 0.10105(7) 0.60373(5) 0.0295(2) Uani 1 1 d . . . . .
O2 O 0.94862(8) 0.43509(7) 0.40933(5) 0.0299(2) Uani 1 1 d . . . . .
H2 H 0.923802 0.489303 0.412980 0.045 Uiso 1 1 calc GR . . . .
O3 O 0.83499(8) 0.56503(7) 0.45891(5) 0.0315(2) Uani 1 1 d . . . . .
O4 O 0.77786(8) 0.51981(6) 0.55788(5) 0.0277(2) Uani 1 1 d . . . . .
N1 N 0.73471(8) 0.16535(7) 0.53845(5) 0.0186(2) Uani 1 1 d . . . . .
C1 C 0.57042(10) 0.18632(9) 0.59678(6) 0.0206(2) Uani 1 1 d . . . . .
C2 C 0.65814(9) 0.22212(8) 0.56299(6) 0.0182(2) Uani 1 1 d . . . . .
C3 C 0.79953(9) 0.22683(8) 0.50837(6) 0.0179(2) Uani 1 1 d . . . . .
C4 C 0.88164(10) 0.20153(9) 0.47154(6) 0.0205(2) Uani 1 1 d . . . . .
H4 H 0.903717 0.137675 0.469078 0.025 Uiso 1 1 calc R . . . .
C5 C 0.92814(10) 0.27374(10) 0.43939(7) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.981578 0.258352 0.413890 0.028 Uiso 1 1 calc R . . . .
C6 C 0.89692(10) 0.37089(9) 0.44403(6) 0.0220(2) Uani 1 1 d . . . . .
C7 C 0.82042(10) 0.39808(9) 0.48431(6) 0.0197(2) Uani 1 1 d . . . . .
C8 C 0.76597(9) 0.32296(8) 0.51505(6) 0.0175(2) Uani 1 1 d . . . . .
C9 C 0.67447(9) 0.31849(8) 0.54961(6) 0.0180(2) Uani 1 1 d . . . . .
C10 C 0.59804(10) 0.39581(9) 0.56609(7) 0.0224(2) Uani 1 1 d . . . . .
H10A H 0.585291 0.444273 0.528218 0.027 Uiso 1 1 calc R . . . .
H10B H 0.633494 0.426981 0.611492 0.027 Uiso 1 1 calc R . . . .
C11 C 0.48566(10) 0.35240(9) 0.57132(7) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.442171 0.400781 0.589362 0.029 Uiso 1 1 calc R . . . .
H11B H 0.443502 0.332962 0.523508 0.029 Uiso 1 1 calc R . . . .
C12 C 0.50356(10) 0.26509(10) 0.62178(7) 0.0245(3) Uani 1 1 d . . . . .
H12A H 0.542609 0.285505 0.670046 0.029 Uiso 1 1 calc R . . . .
H12B H 0.431080 0.239546 0.624433 0.029 Uiso 1 1 calc R . . . .
C13 C 0.75985(10) 0.06506(8) 0.55069(6) 0.0186(2) Uani 1 1 d . . . . .
C14 C 0.86708(10) 0.03958(9) 0.58953(6) 0.0207(2) Uani 1 1 d . . . . .
H14 H 0.919780 0.087112 0.607854 0.025 Uiso 1 1 calc R . . . .
C15 C 0.89506(11) -0.05715(9) 0.60083(7) 0.0244(3) Uani 1 1 d . . . . .
H15 H 0.967050 -0.074640 0.626051 0.029 Uiso 1 1 calc R . . . .
C16 C 0.81561(11) -0.12771(9) 0.57448(7) 0.0266(3) Uani 1 1 d . . . . .
H16 H 0.833838 -0.192475 0.583077 0.032 Uiso 1 1 calc R . . . .
C17 C 0.70878(11) -0.10186(9) 0.53523(7) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.655975 -0.149474 0.517327 0.029 Uiso 1 1 calc R . . . .
C18 C 0.68058(10) -0.00560(9) 0.52267(6) 0.0205(2) Uani 1 1 d . . . . .
H18 H 0.609467 0.011684 0.495804 0.025 Uiso 1 1 calc R . . . .
C19 C 0.81006(10) 0.50160(9) 0.49723(7) 0.0233(3) Uani 1 1 d . . . . .
C20 C 0.77843(12) 0.61943(9) 0.57991(9) 0.0320(3) Uani 1 1 d . . . . .
H20A H 0.775715 0.660430 0.538868 0.048 Uiso 1 1 calc GR . . . .
H20B H 0.845750 0.632432 0.616475 0.048 Uiso 1 1 calc GR . . . .
H20C H 0.714209 0.631717 0.599039 0.048 Uiso 1 1 calc GR . . . .
O1A O 0.93659(8) 0.52198(7) 0.73208(5) 0.0292(2) Uani 1 1 d . . . . .
O2A O 0.49760(8) 0.18414(8) 0.88824(5) 0.0293(2) Uani 1 1 d . . . . .
H2A H 0.520858 0.129510 0.884000 0.044 Uiso 1 1 calc GR . . . .
O3A O 0.60398(8) 0.05436(7) 0.83736(5) 0.0314(2) Uani 1 1 d . . . . .
O4A O 0.70014(8) 0.09951(6) 0.75714(5) 0.0267(2) Uani 1 1 d . . . . .
N1A N 0.75513(8) 0.45376(7) 0.79377(6) 0.0209(2) Uani 1 1 d . . . . .
C1A C 0.91320(10) 0.43646(9) 0.73129(6) 0.0210(2) Uani 1 1 d . . . . .
C2A C 0.82582(10) 0.39742(9) 0.76417(6) 0.0191(2) Uani 1 1 d . . . . .
C3A C 0.68261(10) 0.39251(9) 0.81671(6) 0.0203(2) Uani 1 1 d . . . . .
C4A C 0.59762(10) 0.41905(10) 0.85059(7) 0.0238(3) Uani 1 1 d . . . . .
H4A H 0.582038 0.483578 0.857371 0.029 Uiso 1 1 calc R . . . .
C5A C 0.53835(10) 0.34679(10) 0.87335(7) 0.0259(3) Uani 1 1 d . . . . .
H5A H 0.482369 0.362473 0.896720 0.031 Uiso 1 1 calc R . . . .
C6A C 0.56061(10) 0.24911(10) 0.86201(6) 0.0236(3) Uani 1 1 d . . . . .
C7A C 0.64061(10) 0.22157(9) 0.82420(6) 0.0206(2) Uani 1 1 d . . . . .
C8A C 0.70650(10) 0.29595(9) 0.80163(6) 0.0189(2) Uani 1 1 d . . . . .
C9A C 0.79997(10) 0.30058(8) 0.76839(6) 0.0183(2) Uani 1 1 d . . . . .
C10A C 0.87007(10) 0.22427(9) 0.74362(6) 0.0202(2) Uani 1 1 d . . . . .
H10C H 0.830066 0.199788 0.696730 0.024 Uiso 1 1 calc R . . . .
H10D H 0.882189 0.170947 0.777635 0.024 Uiso 1 1 calc R . . . .
C11A C 0.98366(10) 0.26515(9) 0.73806(7) 0.0223(2) Uani 1 1 d . . . . .
H11C H 1.030488 0.275188 0.786410 0.027 Uiso 1 1 calc R . . . .
H11D H 1.020935 0.218528 0.713855 0.027 Uiso 1 1 calc R . . . .
C12A C 0.97158(11) 0.36051(9) 0.69650(7) 0.0238(3) Uani 1 1 d . . . . .
H12C H 1.045446 0.383715 0.694757 0.029 Uiso 1 1 calc R . . . .
H12D H 0.928959 0.349705 0.647149 0.029 Uiso 1 1 calc R . . . .
C13A C 0.76141(10) 0.55561(9) 0.80807(7) 0.0203(2) Uani 1 1 d . . . . .
C14A C 0.82345(11) 0.58919(9) 0.87453(7) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.861858 0.546051 0.909206 0.029 Uiso 1 1 calc R . . . .
C15A C 0.82774(11) 0.68748(10) 0.88884(7) 0.0260(3) Uani 1 1 d . . . . .
H15A H 0.869458 0.710243 0.933171 0.031 Uiso 1 1 calc R . . . .
C16A C 0.77021(10) 0.75182(9) 0.83742(7) 0.0245(3) Uani 1 1 d . . . . .
H16A H 0.773344 0.817654 0.847146 0.029 Uiso 1 1 calc R . . . .
C17A C 0.70789(11) 0.71775(10) 0.77137(8) 0.0277(3) Uani 1 1 d . . . . .
H17A H 0.669457 0.760877 0.736690 0.033 Uiso 1 1 calc R . . . .
C18A C 0.70272(11) 0.61951(10) 0.75688(7) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.659904 0.596689 0.712874 0.032 Uiso 1 1 calc R . . . .
C19A C 0.64687(10) 0.11826(9) 0.80821(7) 0.0224(2) Uani 1 1 d . . . . .
C20A C 0.71211(13) -0.00093(9) 0.74016(9) 0.0325(3) Uani 1 1 d . . . . .
H20D H 0.749508 -0.005838 0.701447 0.049 Uiso 1 1 calc GR . . . .
H20E H 0.639209 -0.030170 0.725576 0.049 Uiso 1 1 calc GR . . . .
H20F H 0.755554 -0.033544 0.782156 0.049 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
O1 C1 1.2196(16) . ?
O2 H2 0.8200 . ?
O2 C6 1.3540(15) . ?
O3 C19 1.2272(16) . ?
O4 C19 1.3316(17) . ?
O4 C20 1.4423(15) . ?
N1 C2 1.3902(15) . ?
N1 C3 1.3808(15) . ?
N1 C13 1.4306(15) . ?
C1 C2 1.4675(16) . ?
C1 C12 1.5101(17) . ?
C2 C9 1.3834(16) . ?
C3 C4 1.4041(17) . ?
C3 C8 1.4093(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3676(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.4085(18) . ?
C6 C7 1.3995(17) . ?
C7 C8 1.4359(16) . ?
C7 C19 1.4663(17) . ?
C8 C9 1.4335(16) . ?
C9 C10 1.5062(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5299(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5273(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.3903(17) . ?
C13 C18 1.3925(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3877(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3864(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.3899(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3845(17) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1A C1A 1.2188(16) . ?
O2A H2A 0.8200 . ?
O2A C6A 1.3582(15) . ?
O3A C19A 1.2290(16) . ?
O4A C19A 1.3216(16) . ?
O4A C20A 1.4446(15) . ?
N1A C2A 1.3842(15) . ?
N1A C3A 1.3752(16) . ?
N1A C13A 1.4362(15) . ?
C1A C2A 1.4693(17) . ?
C1A C12A 1.5129(17) . ?
C2A C9A 1.3858(17) . ?
C3A C4A 1.4015(17) . ?
C3A C8A 1.4142(17) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3681(19) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.408(2) . ?
C6A C7A 1.4032(17) . ?
C7A C8A 1.4384(17) . ?
C7A C19A 1.4696(18) . ?
C8A C9A 1.4392(16) . ?
C9A C10A 1.5090(16) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.5320(17) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.5290(18) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A C14A 1.3896(17) . ?
C13A C18A 1.3831(18) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.3877(19) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.3848(19) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.3869(19) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3877(19) . ?
C18A H18A 0.9300 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 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
C6 O2 H2 109.5 . . ?
C19 O4 C20 116.86(10) . . ?
C2 N1 C13 129.18(10) . . ?
C3 N1 C2 107.10(9) . . ?
C3 N1 C13 122.95(10) . . ?
O1 C1 C2 124.07(11) . . ?
O1 C1 C12 121.99(11) . . ?
C2 C1 C12 113.93(10) . . ?
N1 C2 C1 125.66(11) . . ?
C9 C2 N1 110.17(10) . . ?
C9 C2 C1 124.16(11) . . ?
N1 C3 C4 127.43(11) . . ?
N1 C3 C8 109.61(10) . . ?
C4 C3 C8 122.81(11) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.91(11) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.48(11) . . ?
C6 C5 H5 119.3 . . ?
O2 C6 C5 115.52(11) . . ?
O2 C6 C7 123.08(12) . . ?
C7 C6 C5 121.36(11) . . ?
C6 C7 C8 117.89(11) . . ?
C6 C7 C19 116.88(11) . . ?
C8 C7 C19 124.98(11) . . ?
C3 C8 C7 118.28(11) . . ?
C3 C8 C9 106.20(10) . . ?
C9 C8 C7 135.37(11) . . ?
C2 C9 C8 106.89(10) . . ?
C2 C9 C10 121.55(10) . . ?
C8 C9 C10 131.40(11) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 C11 110.51(10) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C10 110.94(10) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C1 C12 C11 112.41(10) . . ?
C1 C12 H12A 109.1 . . ?
C1 C12 H12B 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 N1 118.20(10) . . ?
C14 C13 C18 120.59(11) . . ?
C18 C13 N1 121.18(11) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.65(11) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.95(12) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.15(12) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.34(12) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.28(11) . . ?
C17 C18 H18 120.4 . . ?
O3 C19 O4 123.24(12) . . ?
O3 C19 C7 123.85(12) . . ?
O4 C19 C7 112.76(10) . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6A O2A H2A 109.5 . . ?
C19A O4A C20A 116.69(10) . . ?
C2A N1A C13A 128.42(10) . . ?
C3A N1A C2A 107.36(10) . . ?
C3A N1A C13A 123.76(10) . . ?
O1A C1A C2A 123.16(11) . . ?
O1A C1A C12A 123.15(11) . . ?
C2A C1A C12A 113.69(10) . . ?
N1A C2A C1A 124.01(11) . . ?
N1A C2A C9A 110.36(10) . . ?
C9A C2A C1A 125.60(11) . . ?
N1A C3A C4A 126.50(12) . . ?
N1A C3A C8A 109.74(10) . . ?
C4A C3A C8A 123.76(12) . . ?
C3A C4A H4A 121.1 . . ?
C5A C4A C3A 117.73(12) . . ?
C5A C4A H4A 121.1 . . ?
C4A C5A H5A 119.4 . . ?
C4A C5A C6A 121.17(12) . . ?
C6A C5A H5A 119.4 . . ?
O2A C6A C5A 115.61(11) . . ?
O2A C6A C7A 122.64(12) . . ?
C7A C6A C5A 121.73(12) . . ?
C6A C7A C8A 118.14(11) . . ?
C6A C7A C19A 116.70(11) . . ?
C8A C7A C19A 125.11(11) . . ?
C3A C8A C7A 117.29(11) . . ?
C3A C8A C9A 105.87(10) . . ?
C7A C8A C9A 136.77(11) . . ?
C2A C9A C8A 106.66(10) . . ?
C2A C9A C10A 120.32(10) . . ?
C8A C9A C10A 132.94(11) . . ?
C9A C10A H10C 109.4 . . ?
C9A C10A H10D 109.4 . . ?
C9A C10A C11A 111.06(10) . . ?
H10C C10A H10D 108.0 . . ?
C11A C10A H10C 109.4 . . ?
C11A C10A H10D 109.4 . . ?
C10A C11A H11C 109.1 . . ?
C10A C11A H11D 109.1 . . ?
H11C C11A H11D 107.9 . . ?
C12A C11A C10A 112.29(10) . . ?
C12A C11A H11C 109.1 . . ?
C12A C11A H11D 109.1 . . ?
C1A C12A C11A 111.83(10) . . ?
C1A C12A H12C 109.2 . . ?
C1A C12A H12D 109.2 . . ?
C11A C12A H12C 109.2 . . ?
C11A C12A H12D 109.2 . . ?
H12C C12A H12D 107.9 . . ?
C14A C13A N1A 119.61(11) . . ?
C18A C13A N1A 120.06(11) . . ?
C18A C13A C14A 120.29(12) . . ?
C13A C14A H14A 120.2 . . ?
C15A C14A C13A 119.60(12) . . ?
C15A C14A H14A 120.2 . . ?
C14A C15A H15A 119.8 . . ?
C16A C15A C14A 120.31(12) . . ?
C16A C15A H15A 119.8 . . ?
C15A C16A H16A 120.1 . . ?
C15A C16A C17A 119.78(12) . . ?
C17A C16A H16A 120.1 . . ?
C16A C17A H17A 119.9 . . ?
C16A C17A C18A 120.19(12) . . ?
C18A C17A H17A 119.9 . . ?
C13A C18A C17A 119.82(12) . . ?
C13A C18A H18A 120.1 . . ?
C17A C18A H18A 120.1 . . ?
O3A C19A O4A 122.16(12) . . ?
O3A C19A C7A 123.99(12) . . ?
O4A C19A C7A 113.81(10) . . ?
O4A C20A H20D 109.5 . . ?
O4A C20A H20E 109.5 . . ?
O4A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 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
O1 C1 C2 N1 -4.11(19) . . . . ?
O1 C1 C2 C9 174.38(12) . . . . ?
O1 C1 C12 C11 -143.68(12) . . . . ?
O2 C6 C7 C8 176.34(11) . . . . ?
O2 C6 C7 C19 -9.08(17) . . . . ?
N1 C2 C9 C8 -0.12(13) . . . . ?
N1 C2 C9 C10 175.83(10) . . . . ?
N1 C3 C4 C5 173.37(11) . . . . ?
N1 C3 C8 C7 -177.52(10) . . . . ?
N1 C3 C8 C9 -1.29(13) . . . . ?
N1 C13 C14 C15 -178.42(11) . . . . ?
N1 C13 C18 C17 179.39(11) . . . . ?
C1 C2 C9 C8 -178.82(10) . . . . ?
C1 C2 C9 C10 -2.87(18) . . . . ?
C2 N1 C3 C4 -174.46(11) . . . . ?
C2 N1 C3 C8 1.22(13) . . . . ?
C2 N1 C13 C14 -115.71(13) . . . . ?
C2 N1 C13 C18 66.27(17) . . . . ?
C2 C1 C12 C11 35.40(14) . . . . ?
C2 C9 C10 C11 -20.41(16) . . . . ?
C3 N1 C2 C1 178.00(11) . . . . ?
C3 N1 C2 C9 -0.67(13) . . . . ?
C3 N1 C13 C14 52.92(16) . . . . ?
C3 N1 C13 C18 -125.09(12) . . . . ?
C3 C4 C5 C6 1.29(18) . . . . ?
C3 C8 C9 C2 0.85(13) . . . . ?
C3 C8 C9 C10 -174.55(12) . . . . ?
C4 C3 C8 C7 -1.60(17) . . . . ?
C4 C3 C8 C9 174.63(10) . . . . ?
C4 C5 C6 O2 -179.49(11) . . . . ?
C4 C5 C6 C7 2.72(18) . . . . ?
C5 C6 C7 C8 -6.04(17) . . . . ?
C5 C6 C7 C19 168.54(11) . . . . ?
C6 C7 C8 C3 5.40(16) . . . . ?
C6 C7 C8 C9 -169.44(12) . . . . ?
C6 C7 C19 O3 23.17(18) . . . . ?
C6 C7 C19 O4 -152.55(11) . . . . ?
C7 C8 C9 C2 176.13(12) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C3 C4 C5 -1.79(17) . . . . ?
C8 C7 C19 O3 -162.67(12) . . . . ?
C8 C7 C19 O4 21.61(17) . . . . ?
C8 C9 C10 C11 154.42(12) . . . . ?
C9 C10 C11 C12 50.18(14) . . . . ?
C10 C11 C12 C1 -59.39(14) . . . . ?
C12 C1 C2 N1 176.84(11) . . . . ?
C12 C1 C2 C9 -4.67(17) . . . . ?
C13 N1 C2 C1 -11.96(19) . . . . ?
C13 N1 C2 C9 169.36(11) . . . . ?
C13 N1 C3 C4 14.74(18) . . . . ?
C13 N1 C3 C8 -169.58(10) . . . . ?
C13 C14 C15 C16 -1.11(19) . . . . ?
C14 C13 C18 C17 1.42(18) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C13 -0.96(19) . . . . ?
C18 C13 C14 C15 -0.39(18) . . . . ?
C19 C7 C8 C3 -168.70(11) . . . . ?
C19 C7 C8 C9 16.5(2) . . . . ?
C20 O4 C19 O3 -3.06(18) . . . . ?
C20 O4 C19 C7 172.69(11) . . . . ?
O1A C1A C2A N1A 5.65(19) . . . . ?
O1A C1A C2A C9A -176.24(12) . . . . ?
O1A C1A C12A C11A 145.16(12) . . . . ?
O2A C6A C7A C8A -177.18(10) . . . . ?
O2A C6A C7A C19A 5.27(17) . . . . ?
N1A C2A C9A C8A 0.87(13) . . . . ?
N1A C2A C9A C10A -176.33(10) . . . . ?
N1A C3A C4A C5A -176.17(12) . . . . ?
N1A C3A C8A C7A 178.09(10) . . . . ?
N1A C3A C8A C9A 0.67(13) . . . . ?
N1A C13A C14A C15A -178.78(11) . . . . ?
N1A C13A C18A C17A 179.14(12) . . . . ?
C1A C2A C9A C8A -177.46(11) . . . . ?
C1A C2A C9A C10A 5.33(18) . . . . ?
C2A N1A C3A C4A 179.37(12) . . . . ?
C2A N1A C3A C8A -0.15(13) . . . . ?
C2A N1A C13A C14A -89.41(15) . . . . ?
C2A N1A C13A C18A 92.89(16) . . . . ?
C2A C1A C12A C11A -34.74(14) . . . . ?
C2A C9A C10A C11A 17.44(15) . . . . ?
C3A N1A C2A C1A 177.90(11) . . . . ?
C3A N1A C2A C9A -0.46(13) . . . . ?
C3A N1A C13A C14A 81.84(15) . . . . ?
C3A N1A C13A C18A -95.87(15) . . . . ?
C3A C4A C5A C6A -1.09(18) . . . . ?
C3A C8A C9A C2A -0.92(13) . . . . ?
C3A C8A C9A C10A 175.78(12) . . . . ?
C4A C3A C8A C7A -1.44(18) . . . . ?
C4A C3A C8A C9A -178.86(11) . . . . ?
C4A C5A C6A O2A 178.83(11) . . . . ?
C4A C5A C6A C7A -2.91(19) . . . . ?
C5A C6A C7A C8A 4.68(18) . . . . ?
C5A C6A C7A C19A -172.87(11) . . . . ?
C6A C7A C8A C3A -2.51(16) . . . . ?
C6A C7A C8A C9A 173.87(12) . . . . ?
C6A C7A C19A O3A -14.92(18) . . . . ?
C6A C7A C19A O4A 162.85(11) . . . . ?
C7A C8A C9A C2A -177.58(13) . . . . ?
C7A C8A C9A C10A -0.9(2) . . . . ?
C8A C3A C4A C5A 3.27(18) . . . . ?
C8A C7A C19A O3A 167.72(12) . . . . ?
C8A C7A C19A O4A -14.51(17) . . . . ?
C8A C9A C10A C11A -158.90(12) . . . . ?
C9A C10A C11A C12A -48.52(13) . . . . ?
C10A C11A C12A C1A 58.48(14) . . . . ?
C12A C1A C2A N1A -174.46(11) . . . . ?
C12A C1A C2A C9A 3.66(17) . . . . ?
C13A N1A C2A C1A -9.72(19) . . . . ?
C13A N1A C2A C9A 171.92(11) . . . . ?
C13A N1A C3A C4A 6.54(19) . . . . ?
C13A N1A C3A C8A -172.97(10) . . . . ?
C13A C14A C15A C16A 0.30(19) . . . . ?
C14A C13A C18A C17A 1.4(2) . . . . ?
C14A C15A C16A C17A 0.10(19) . . . . ?
C15A C16A C17A C18A 0.3(2) . . . . ?
C16A C17A C18A C13A -1.1(2) . . . . ?
C18A C13A C14A C15A -1.07(19) . . . . ?
C19A C7A C8A C3A 174.81(11) . . . . ?
C19A C7A C8A C9A -8.8(2) . . . . ?
C20A O4A C19A O3A -3.87(18) . . . . ?
C20A O4A C19A C7A 178.31(11) . . . . ?

_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 'Vapour deposition'
