#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:41:47 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571159.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571159
loop_
_publ_author_name
'Biswas, Soumen'
'Hughes, William B.'
'De Angelis, Luca'
'Haug, Graham C.'
'Trevino, Ramon'
'Fremin, Seth O.'
'Arman, Hadi D.'
'Larionov, Oleg V.'
'Doyle, Michael P.'
_publ_section_title
;
 The “cesium effect” magnified: exceptional chemoselectivity
 in cesium ion mediated nucleophilic reactions
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              5277
_journal_page_last               5283
_journal_paper_doi               10.1039/D4SC00316K
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C16 H15 N O5'
_chemical_formula_sum            'C16 H15 N O5'
_chemical_formula_weight         301.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-19
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-07-26 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.7584(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6843(2)
_cell_length_b                   6.33089(7)
_cell_length_c                   15.89366(18)
_cell_measurement_reflns_used    17076
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8480
_cell_measurement_theta_min      3.3080
_cell_volume                     1433.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     83.00 119.00   0.50    0.07    --   46.54  57.00   0.00   72
  2  ω     83.00 119.00   0.50    0.07    --   46.54  57.00  60.00   72
  3  ω     31.00 119.00   0.50    0.07    --   46.54  54.00 153.90  176
  4  ω     31.00 119.00   0.50    0.07    --   46.54  55.00  46.91  176
  5  ω     31.00 119.00   0.50    0.07    --   46.54  54.00 -51.19  176
  6  ω     31.00 119.00   0.50    0.07    --   46.54  54.00-116.64  176
  7  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00   0.00  142
  8  ω     39.00 100.00   0.50    0.07    --   46.54-134.00  63.00  122
  9  ω     39.00 118.00   0.50    0.30    --  106.40-134.00  63.00  158
 10  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00 120.00  142
 11  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00  90.00  142
 12  ω     39.00 100.00   0.50    0.07    --   46.54-134.00-116.00  122
 13  ω     39.00 118.00   0.50    0.30    --  106.40-134.00-116.00  158
 14  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00-120.00  142
 15  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00-150.00  142
 16  ω     34.00 101.00   0.50    0.30    --  106.40 -77.00-120.00  134
 17  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00 -90.00   74
 18  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00   0.00   74
 19  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00  30.00   74
 20  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00  60.00   74
 21  ω     89.00 178.00   0.50    0.30    --  106.40  15.00-150.00  178
 22  ω     89.00 178.00   0.50    0.30    --  106.40 134.00 130.00  178
 23  ω     91.00 178.00   0.50    0.30    --  106.40  61.00  30.00  174
 24  ω     89.00 178.00   0.50    0.30    --  106.40 134.00 -49.00  178
 25  ω    -92.00 -18.00   0.50    0.07    --  -46.54 134.00 -49.00  148
 26  ω    -85.00 -19.00   0.50    0.30    --  -91.75 125.00-180.00  132
 27  ω    -92.00 -19.00   0.50    0.30    --  -91.75 134.00 -49.00  146
 28  ω    -92.00 -18.00   0.50    0.07    --  -46.54 134.00 130.00  148
 29  ω    -92.00 -19.00   0.50    0.30    --  -91.75 134.00 130.00  146
 30  ω   -101.00 -19.00   0.50    0.30    --  -91.75  77.00 150.00  164
 31  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 150.00   64
 32  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00   0.00   64
 33  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -30.00   64
 34  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -60.00   64
 35  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00-180.00   64
 36  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -90.00   64
 37  ω   -101.00 -19.00   0.50    0.30    --  -91.75  77.00 -30.00  164
 38  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00  90.00   64
 39  ω    -30.00  29.00   0.50    0.07    --  -46.54  19.00  90.00  118
 40  ω   -119.00 -32.00   0.50    0.07    --  -46.54 -42.00 -24.02  174
 41  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 150.00   70
 42  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 -30.00   70
 43  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 -60.00   70
 44  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00-180.00   70
 45  ω   -166.00 -76.00   0.50    0.30    --  -91.75 -30.00-120.00  180
 46  ω   -118.00 -68.00   0.50    0.07    --  -46.54-134.00-116.00  100
 47  ω   -161.00 -68.00   0.50    0.30    --  -91.75-134.00-116.00  186
 48  ω   -164.00-101.00   0.50    0.30    --  -91.75 -77.00 -30.00  126
 49  ω   -118.00 -68.00   0.50    0.07    --  -46.54-134.00  63.00  100
 50  ω   -118.00 -88.00   0.50    0.07    --  -46.54-125.00   0.00   60
 51  ω   -161.00 -68.00   0.50    0.30    --  -91.75-134.00  63.00  186
 52  ω   -164.00 -91.00   0.50    0.30    --  -91.75 -61.00 150.00  146
;
_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      -0.1052980000
_diffrn_orient_matrix_UB_12      0.0285234000
_diffrn_orient_matrix_UB_13      -0.0245260000
_diffrn_orient_matrix_UB_21      -0.0123279000
_diffrn_orient_matrix_UB_22      -0.2417718000
_diffrn_orient_matrix_UB_23      -0.0027209000
_diffrn_orient_matrix_UB_31      0.0213884000
_diffrn_orient_matrix_UB_32      0.0004321000
_diffrn_orient_matrix_UB_33      0.1038278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.475
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+0.5133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2657
_reflns_number_total             2921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc00316k3.cif
_cod_data_source_block           hpd614c_auto
_cod_depositor_comments
'Adding full bibliography for 1571157--1571159.cif.'
_cod_database_code               1571159
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB-1-65B
_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.
;
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C13(H13), C11(H11), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.826
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O3 O 0.41999(6) -0.01476(12) 0.19312(5) 0.02415(19) Uani 1 1 d . . . . .
O5 O 0.18008(6) -0.99421(13) 0.03397(5) 0.0269(2) Uani 1 1 d . . . . .
O2 O 0.42686(6) -0.18264(13) 0.32064(5) 0.0264(2) Uani 1 1 d . . . . .
N1 N 0.25341(7) -0.65632(15) 0.13385(6) 0.0201(2) Uani 1 1 d . . . . .
O4 O 0.17870(7) -0.84505(15) -0.09437(6) 0.0346(2) Uani 1 1 d . . . . .
O1 O 0.28056(6) -0.49435(12) 0.26946(5) 0.02312(19) Uani 1 1 d . . . . .
C2 C 0.34838(8) -0.34657(17) 0.17199(7) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.26236(8) -0.67871(17) 0.05245(7) 0.0201(2) Uani 1 1 d . . . . .
C14 C 0.20373(8) -0.84899(18) -0.01174(7) 0.0209(2) Uani 1 1 d . . . . .
C3 C 0.35827(8) -0.37214(18) 0.09105(7) 0.0215(2) Uani 1 1 d . . . . .
H3 H 0.394615 -0.271912 0.075765 0.026 Uiso 1 1 calc R U . . .
C4 C 0.31668(8) -0.54164(18) 0.02896(7) 0.0210(2) Uani 1 1 d . . . . .
C6 C 0.40055(8) -0.17583(17) 0.23776(7) 0.0206(2) Uani 1 1 d . . . . .
C8 C 0.33787(8) -0.56843(19) -0.05335(7) 0.0228(2) Uani 1 1 d . . . . .
C15 C 0.11441(9) -1.1554(2) -0.02144(8) 0.0307(3) Uani 1 1 d . . . . .
H15A H 0.147739 -1.266732 -0.039627 0.037 Uiso 1 1 calc R U . . .
H15B H 0.065751 -1.092425 -0.078280 0.037 Uiso 1 1 calc R U . . .
C9 C 0.38049(8) -0.7533(2) -0.06432(8) 0.0268(3) Uani 1 1 d . . . . .
H9 H 0.395125 -0.862859 -0.019585 0.032 Uiso 1 1 calc R U . . .
C13 C 0.31816(8) -0.4079(2) -0.11887(8) 0.0272(3) Uani 1 1 d . . . . .
H13 H 0.290247 -0.280189 -0.111448 0.033 Uiso 1 1 calc R U . . .
C7 C 0.47950(9) 0.14791(19) 0.25271(9) 0.0301(3) Uani 1 1 d . . . . .
H7A H 0.489392 0.258987 0.214781 0.045 Uiso 1 1 calc R U . . .
H7B H 0.540132 0.086521 0.293644 0.045 Uiso 1 1 calc R U . . .
H7C H 0.449333 0.208521 0.290126 0.045 Uiso 1 1 calc R U . . .
C11 C 0.38080(9) -0.6183(2) -0.20574(8) 0.0324(3) Uani 1 1 d . . . . .
H11 H 0.395120 -0.635784 -0.257786 0.039 Uiso 1 1 calc R U . . .
C10 C 0.40164(9) -0.7781(2) -0.14029(9) 0.0319(3) Uani 1 1 d . . . . .
H10 H 0.430437 -0.904667 -0.147498 0.038 Uiso 1 1 calc R U . . .
C1 C 0.29379(8) -0.49683(17) 0.19843(7) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.33916(9) -0.4337(2) -0.19510(8) 0.0313(3) Uani 1 1 d . . . . .
H12 H 0.324888 -0.324309 -0.239878 0.038 Uiso 1 1 calc R U . . .
C16 C 0.07041(11) -1.2467(2) 0.03857(9) 0.0419(4) Uani 1 1 d . . . . .
H16A H 0.018638 -1.340525 0.001313 0.063 Uiso 1 1 calc R U . . .
H16B H 0.046320 -1.131883 0.063901 0.063 Uiso 1 1 calc R U . . .
H16C H 0.117665 -1.326926 0.089507 0.063 Uiso 1 1 calc R U . . .
H1 H 0.2190(13) -0.757(3) 0.1506(12) 0.050 Uiso 1 1 d . U . . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 10 0.0609
-3 -4 0 0.0617
3 1 -10 0.0477
2 3 4 0.0652
-4 0 10 0.0613
-9 1 0 0.0473
5 -1 -10 0.0438
8 -1 2 0.0386
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 O3 C7 114.86(9) . . ?
C14 O5 C15 116.55(9) . . ?
C5 N1 C1 125.41(9) . . ?
C5 N1 H1 119.8(11) . . ?
C1 N1 H1 114.7(11) . . ?
C3 C2 C6 120.06(10) . . ?
C3 C2 C1 120.43(10) . . ?
C1 C2 C6 119.28(9) . . ?
N1 C5 C14 116.14(9) . . ?
N1 C5 C4 120.90(10) . . ?
C4 C5 C14 122.77(9) . . ?
O5 C14 C5 111.07(9) . . ?
O4 C14 O5 125.29(11) . . ?
O4 C14 C5 123.56(10) . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 122.91(10) . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 116.49(10) . . ?
C5 C4 C8 124.02(10) . . ?
C3 C4 C8 119.40(10) . . ?
O3 C6 C2 111.02(9) . . ?
O2 C6 O3 123.57(10) . . ?
O2 C6 C2 125.30(10) . . ?
C9 C8 C4 120.05(10) . . ?
C13 C8 C4 120.82(11) . . ?
C13 C8 C9 119.10(10) . . ?
O5 C15 H15A 110.5 . . ?
O5 C15 H15B 110.5 . . ?
O5 C15 C16 106.35(10) . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.34(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.37(12) . . ?
C12 C13 H13 119.8 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 119.94(11) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.15(12) . . ?
C11 C10 H10 119.9 . . ?
N1 C1 C2 113.78(9) . . ?
O1 C1 N1 119.16(10) . . ?
O1 C1 C2 127.06(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.09(12) . . ?
C11 C12 H12 120.0 . . ?
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 . . ?
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
O3 C6 1.3482(13) . ?
O3 C7 1.4451(14) . ?
O5 C14 1.3177(13) . ?
O5 C15 1.4553(14) . ?
O2 C6 1.2050(13) . ?
N1 C5 1.3659(13) . ?
N1 C1 1.3892(14) . ?
N1 H1 0.941(19) . ?
O4 C14 1.2033(14) . ?
O1 C1 1.2305(13) . ?
C2 C3 1.3683(15) . ?
C2 C6 1.4881(15) . ?
C2 C1 1.4547(15) . ?
C5 C14 1.5042(15) . ?
C5 C4 1.3728(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.4183(16) . ?
C4 C8 1.4882(14) . ?
C8 C9 1.3946(17) . ?
C8 C13 1.3941(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5070(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3887(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.3918(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C10 1.388(2) . ?
C11 C12 1.384(2) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
N1 C5 C14 O5 -22.76(13) . . . . ?
N1 C5 C14 O4 153.96(11) . . . . ?
N1 C5 C4 C3 -3.06(16) . . . . ?
N1 C5 C4 C8 173.40(10) . . . . ?
C2 C3 C4 C5 2.01(17) . . . . ?
C2 C3 C4 C8 -174.62(10) . . . . ?
C5 N1 C1 O1 -179.83(10) . . . . ?
C5 N1 C1 C2 0.51(15) . . . . ?
C5 C4 C8 C9 -56.87(16) . . . . ?
C5 C4 C8 C13 125.04(13) . . . . ?
C14 O5 C15 C16 -158.73(11) . . . . ?
C14 C5 C4 C3 171.90(10) . . . . ?
C14 C5 C4 C8 -11.64(17) . . . . ?
C3 C2 C6 O3 26.23(14) . . . . ?
C3 C2 C6 O2 -150.08(11) . . . . ?
C3 C2 C1 N1 -1.57(15) . . . . ?
C3 C2 C1 O1 178.81(11) . . . . ?
C3 C4 C8 C9 119.49(12) . . . . ?
C3 C4 C8 C13 -58.59(15) . . . . ?
C4 C5 C14 O5 162.06(10) . . . . ?
C4 C5 C14 O4 -21.22(17) . . . . ?
C4 C8 C9 C10 -179.10(11) . . . . ?
C4 C8 C13 C12 179.32(11) . . . . ?
C6 C2 C3 C4 174.77(10) . . . . ?
C6 C2 C1 N1 -176.05(9) . . . . ?
C6 C2 C1 O1 4.32(17) . . . . ?
C8 C9 C10 C11 0.26(18) . . . . ?
C8 C13 C12 C11 -0.73(18) . . . . ?
C15 O5 C14 O4 -3.42(17) . . . . ?
C15 O5 C14 C5 173.24(10) . . . . ?
C9 C8 C13 C12 1.21(17) . . . . ?
C13 C8 C9 C10 -0.98(17) . . . . ?
C7 O3 C6 O2 2.90(15) . . . . ?
C7 O3 C6 C2 -173.49(9) . . . . ?
C10 C11 C12 C13 0.01(19) . . . . ?
C1 N1 C5 C14 -173.39(10) . . . . ?
C1 N1 C5 C4 1.90(17) . . . . ?
C1 C2 C3 C4 0.33(17) . . . . ?
C1 C2 C6 O3 -159.27(9) . . . . ?
C1 C2 C6 O2 24.42(16) . . . . ?
C12 C11 C10 C9 0.23(19) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.9947 -0.7351 10.0699 0.0474 0.1873 0.9812
-3.3374 -3.8519 0.3250 0.2336 0.9715 -0.0393
3.0295 0.7807 -10.0542 -0.0501 -0.1987 -0.9788
1.9278 3.4136 4.0830 -0.2058 -0.8602 0.4666
-4.3569 0.3302 10.2858 0.2159 -0.0541 0.9749
-8.7711 1.3973 0.1927 0.9587 -0.2302 -0.1670
5.4539 -0.5110 -10.1424 -0.3401 0.0839 -0.9366
7.6015 -1.2975 2.2578 -0.8928 0.2138 0.3964
