#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:59:52 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/18/1571892.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_1571892
loop_
_publ_author_name
'Nicolai, Stefano'
'Waser, Jérôme'
_publ_section_title
;
 Lewis acid catalyzed [4+2] annulation of bicyclobutanes with dienol
 ethers for the synthesis of bicyclo[4.1.1]octanes.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              10823
_journal_page_last               10829
_journal_paper_doi               10.1039/d4sc02767a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C21 H22 O2'
_chemical_formula_sum            'C21 H22 O2'
_chemical_formula_weight         306.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-21 deposited with the CCDC.	2024-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.9318(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7615(2)
_cell_length_b                   6.40467(8)
_cell_length_c                   13.86477(15)
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.3010
_cell_measurement_theta_min      5.0060
_cell_volume                     1568.76(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.123a 64-bit (release 20-05-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.123a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  31.00   1.00    2.00    --  -40.91  56.00-122.00   89
  2  ω   -112.00 -19.00   1.00    2.00    --  -40.91 -56.00  95.00   93
  3  ω     91.00 171.00   1.00    8.00    --  112.00  56.00-122.00   80
  4  ω     56.00 127.00   1.00    8.00    --  112.00 -56.00  95.00   71
  5  ω     13.00  75.00   1.00    2.00    --   40.91 -99.00 -60.00   62
  6  ω     55.00  94.00   1.00    2.00    --   40.91-125.00  60.00   39
  7  ω     85.00 110.00   1.00    8.00    --  112.00  30.00-150.00   25
  8  ω    105.00 131.00   1.00    8.00    --  112.00  77.00 120.00   26
  9  ω    145.00 175.00   1.00    8.00    --  112.00  77.00 120.00   30
 10  ω    105.00 168.00   1.00    8.00    --  112.00 111.00-120.00   63
 11  ω    105.00 177.00   1.00    8.00    --  112.00  61.00 150.00   72
 12  ω    153.00 178.00   1.00    8.00    --  112.00  30.00-150.00   25
 13  ω     45.00  92.00   1.00    8.00    --  112.00-111.00  60.00   47
 14  ω     39.00 105.00   1.00    8.00    --  112.00-111.00  90.00   66
 15  ω     97.00 149.00   1.00    8.00    --  112.00  45.00-150.00   52
 16  ω    133.00 166.00   1.00    8.00    --  112.00 111.00-150.00   33
 17  ω    108.00 143.00   1.00    8.00    --  112.00 111.00 150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0644620000
_diffrn_orient_matrix_UB_12      -0.1574801000
_diffrn_orient_matrix_UB_13      0.0089572000
_diffrn_orient_matrix_UB_21      -0.0293318000
_diffrn_orient_matrix_UB_22      0.0377697000
_diffrn_orient_matrix_UB_23      -0.1070749000
_diffrn_orient_matrix_UB_31      0.0508459000
_diffrn_orient_matrix_UB_32      -0.1779010000
_diffrn_orient_matrix_UB_33      -0.0305985000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7738
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.026
_diffrn_reflns_theta_min         5.007
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.123a (Rigaku Oxford Diffraction, 2024)
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 pale colourless'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0405
_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)+(0.0660P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2925
_reflns_number_total             3208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02767a2.cif
_cod_data_source_block           ste-24-1162
_cod_depositor_comments
'Adding full bibliography for 1571891--1571893.cif.'
_cod_database_code               1571892
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C21 H22 O2'
_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   0.941
_shelx_estimated_absorpt_t_min   0.673
_olex2_refinement_description
;
;
_olex2_date_sample_data_collection 2024-05-21
_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 6.825
_oxdiff_exptl_absorpt_empirical_full_min 0.492
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'
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 0.94179(5) 0.42003(15) 0.81419(6) 0.0342(2) Uani 1 1 d . . . . .
O2 O 0.75331(5) -0.03495(14) 0.50973(7) 0.0340(2) Uani 1 1 d . . . . .
C1 C 0.92357(6) 0.46732(17) 0.73011(8) 0.0246(2) Uani 1 1 d . . . . .
C2 C 0.97660(6) 0.43609(19) 0.65276(9) 0.0287(3) Uani 1 1 d . . . . .
H2A H 0.9919(9) 0.574(3) 0.6319(12) 0.037(4) Uiso 1 1 d . . . . .
H2B H 1.0222(10) 0.368(3) 0.6814(12) 0.038(4) Uiso 1 1 d . . . . .
C3 C 0.94332(6) 0.30487(19) 0.56628(9) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.9825(9) 0.260(2) 0.5288(11) 0.028(4) Uiso 1 1 d . . . . .
C4 C 0.89116(6) 0.12746(18) 0.59591(9) 0.0259(2) Uani 1 1 d . . . . .
H4A H 0.8988(9) 0.078(3) 0.6645(12) 0.032(4) Uiso 1 1 d . . . . .
H4B H 0.8915(9) 0.006(3) 0.5526(12) 0.033(4) Uiso 1 1 d . . . . .
C5 C 0.82125(6) 0.26943(16) 0.56652(7) 0.0203(2) Uani 1 1 d . . . . .
C6 C 0.79105(5) 0.39161(16) 0.65130(7) 0.0199(2) Uani 1 1 d . . . . .
H6 H 0.7469(8) 0.473(2) 0.6222(10) 0.021(3) Uiso 1 1 d . . . . .
C7 C 0.84621(6) 0.56099(17) 0.69800(7) 0.0221(2) Uani 1 1 d . . . . .
H7 H 0.8528(8) 0.666(2) 0.6472(11) 0.026(3) Uiso 1 1 d . . . . .
C8 C 0.87369(6) 0.39964(18) 0.50461(8) 0.0250(2) Uani 1 1 d . . . . .
H8A H 0.8680(8) 0.550(3) 0.5022(11) 0.026(3) Uiso 1 1 d . . . . .
H8B H 0.8706(9) 0.350(3) 0.4393(11) 0.030(4) Uiso 1 1 d . . . . .
C9 C 0.76563(6) 0.23945(19) 0.72677(8) 0.0266(2) Uani 1 1 d . . . . .
H9A H 0.7376(10) 0.307(3) 0.7743(13) 0.040(4) Uiso 1 1 d . . . . .
H9B H 0.7316(10) 0.132(3) 0.6958(12) 0.040(4) Uiso 1 1 d . . . . .
H9C H 0.8075(9) 0.164(3) 0.7635(11) 0.030(4) Uiso 1 1 d . . . . .
C10 C 0.81313(7) 0.6732(2) 0.78120(9) 0.0304(3) Uani 1 1 d . . . . .
H10A H 0.8111(10) 0.584(3) 0.8390(14) 0.044(4) Uiso 1 1 d . . . . .
H10B H 0.8438(10) 0.801(3) 0.8003(12) 0.040(4) Uiso 1 1 d . . . . .
H10C H 0.7600(10) 0.718(3) 0.7611(13) 0.045(5) Uiso 1 1 d . . . . .
C11 C 0.75485(6) 0.15471(17) 0.51175(7) 0.0224(2) Uani 1 1 d . . . . .
C12 C 0.68880(6) 0.27718(17) 0.46426(7) 0.0211(2) Uani 1 1 d . . . . .
C13 C 0.69458(6) 0.48820(17) 0.43464(7) 0.0230(2) Uani 1 1 d . . . . .
H13 H 0.7414(9) 0.560(3) 0.4426(11) 0.030(4) Uiso 1 1 d . . . . .
C14 C 0.63242(6) 0.59102(18) 0.39155(8) 0.0251(2) Uani 1 1 d . . . . .
H14 H 0.6365(9) 0.730(3) 0.3708(11) 0.031(4) Uiso 1 1 d . . . . .
C15 C 0.56038(6) 0.49316(19) 0.37906(7) 0.0241(2) Uani 1 1 d . . . . .
C16 C 0.49426(7) 0.5991(2) 0.33845(8) 0.0303(3) Uani 1 1 d . . . . .
H16 H 0.4994(9) 0.738(3) 0.3157(11) 0.032(4) Uiso 1 1 d . . . . .
C17 C 0.42529(7) 0.5015(2) 0.33152(9) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.3818(11) 0.579(3) 0.3056(13) 0.046(5) Uiso 1 1 d . . . . .
C18 C 0.41863(7) 0.2939(2) 0.36258(9) 0.0347(3) Uani 1 1 d . . . . .
H18 H 0.3684(11) 0.225(3) 0.3583(13) 0.046(5) Uiso 1 1 d . . . . .
C19 C 0.48166(6) 0.1856(2) 0.39952(8) 0.0290(3) Uani 1 1 d . . . . .
H19 H 0.4783(9) 0.041(3) 0.4195(11) 0.033(4) Uiso 1 1 d . . . . .
C20 C 0.55395(6) 0.28309(18) 0.40952(7) 0.0234(2) Uani 1 1 d . . . . .
C21 C 0.61972(6) 0.17744(17) 0.45028(7) 0.0225(2) Uani 1 1 d . . . . .
H21 H 0.6157(8) 0.037(2) 0.4707(10) 0.024(3) Uiso 1 1 d . . . . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -2 0.3323
2 -2 1 0.3022
1 -2 2 0.2890
2 0 -1 0.0807
-2 -1 1 0.2571
1 2 -1 0.3215
-1 2 0 0.3093
1 0 0 0.0422
-1 0 0 0.0543
-2 -1 -1 0.3076
1 -2 -2 0.3495
9 2 2 0.1826
-11 1 1 0.0928
0 1 1 0.3027
-2 0 -1 0.0950
2 0 1 0.0487
0 0 -1 0.1318
0 0 1 0.1023
5 -2 7 0.1577
-2 -2 7 0.1878
-11 0 4 0.0672
-10 -1 4 0.1148
-11 -1 1 0.0622
-11 0 2 0.0433
1 0 -2 0.1167
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.58(10) . . ?
O1 C1 C7 121.41(10) . . ?
C2 C1 C7 117.00(9) . . ?
C1 C2 H2A 107.7(10) . . ?
C1 C2 H2B 108.9(10) . . ?
C1 C2 C3 114.17(9) . . ?
H2A C2 H2B 106.5(14) . . ?
C3 C2 H2A 111.1(10) . . ?
C3 C2 H2B 108.1(11) . . ?
C2 C3 H3 110.3(9) . . ?
C2 C3 C4 112.84(10) . . ?
C2 C3 C8 115.94(9) . . ?
C4 C3 H3 114.4(9) . . ?
C4 C3 C8 88.20(8) . . ?
C8 C3 H3 113.7(9) . . ?
C3 C4 H4A 117.3(9) . . ?
C3 C4 H4B 112.2(9) . . ?
C3 C4 C5 89.13(8) . . ?
H4A C4 H4B 108.7(13) . . ?
C5 C4 H4A 117.4(9) . . ?
C5 C4 H4B 110.9(10) . . ?
C4 C5 C8 87.20(8) . . ?
C6 C5 C4 115.09(8) . . ?
C6 C5 C8 114.64(8) . . ?
C11 C5 C4 113.80(9) . . ?
C11 C5 C6 108.06(8) . . ?
C11 C5 C8 117.13(9) . . ?
C5 C6 H6 106.1(8) . . ?
C5 C6 C7 114.46(8) . . ?
C7 C6 H6 103.9(8) . . ?
C9 C6 C5 110.23(9) . . ?
C9 C6 H6 109.6(8) . . ?
C9 C6 C7 112.11(8) . . ?
C1 C7 C6 110.91(8) . . ?
C1 C7 H7 107.8(8) . . ?
C1 C7 C10 111.74(9) . . ?
C6 C7 H7 107.1(9) . . ?
C10 C7 C6 111.56(9) . . ?
C10 C7 H7 107.4(9) . . ?
C3 C8 C5 88.57(8) . . ?
C3 C8 H8A 118.8(9) . . ?
C3 C8 H8B 110.9(9) . . ?
C5 C8 H8A 118.8(8) . . ?
C5 C8 H8B 111.2(10) . . ?
H8A C8 H8B 107.6(13) . . ?
C6 C9 H9A 112.8(11) . . ?
C6 C9 H9B 110.9(10) . . ?
C6 C9 H9C 113.9(9) . . ?
H9A C9 H9B 106.0(14) . . ?
H9A C9 H9C 106.4(13) . . ?
H9B C9 H9C 106.3(14) . . ?
C7 C10 H10A 112.9(11) . . ?
C7 C10 H10B 110.0(9) . . ?
C7 C10 H10C 110.6(10) . . ?
H10A C10 H10B 108.8(14) . . ?
H10A C10 H10C 106.3(15) . . ?
H10B C10 H10C 108.0(15) . . ?
O2 C11 C5 120.51(10) . . ?
O2 C11 C12 119.75(10) . . ?
C12 C11 C5 119.66(9) . . ?
C13 C12 C11 123.11(9) . . ?
C21 C12 C11 117.51(10) . . ?
C21 C12 C13 119.37(10) . . ?
C12 C13 H13 121.2(10) . . ?
C14 C13 C12 120.34(10) . . ?
C14 C13 H13 118.4(10) . . ?
C13 C14 H14 120.3(9) . . ?
C13 C14 C15 121.15(10) . . ?
C15 C14 H14 118.5(9) . . ?
C14 C15 C16 122.35(11) . . ?
C20 C15 C14 118.82(10) . . ?
C20 C15 C16 118.82(10) . . ?
C15 C16 H16 118.3(10) . . ?
C17 C16 C15 120.42(12) . . ?
C17 C16 H16 121.3(9) . . ?
C16 C17 H17 118.1(12) . . ?
C16 C17 C18 120.86(11) . . ?
C18 C17 H17 121.0(12) . . ?
C17 C18 H18 120.4(11) . . ?
C19 C18 C17 120.10(11) . . ?
C19 C18 H18 119.5(11) . . ?
C18 C19 H19 121.2(9) . . ?
C18 C19 C20 120.58(12) . . ?
C20 C19 H19 118.2(9) . . ?
C15 C20 C19 119.18(10) . . ?
C21 C20 C15 118.91(10) . . ?
C21 C20 C19 121.90(11) . . ?
C12 C21 C20 121.33(10) . . ?
C12 C21 H21 119.5(9) . . ?
C20 C21 H21 119.2(9) . . ?
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 1.2155(15) . ?
O2 C11 1.2153(15) . ?
C1 C2 1.5119(16) . ?
C1 C7 1.5231(14) . ?
C2 H2A 0.975(19) . ?
C2 H2B 0.969(18) . ?
C2 C3 1.5319(16) . ?
C3 H3 0.955(15) . ?
C3 C4 1.5480(16) . ?
C3 C8 1.5525(15) . ?
C4 H4A 0.999(16) . ?
C4 H4B 0.984(18) . ?
C4 C5 1.5589(14) . ?
C5 C6 1.5531(14) . ?
C5 C8 1.5701(14) . ?
C5 C11 1.5239(14) . ?
C6 H6 0.990(14) . ?
C6 C7 1.5571(14) . ?
C6 C9 1.5318(14) . ?
C7 H7 0.991(15) . ?
C7 C10 1.5275(15) . ?
C8 H8A 0.970(17) . ?
C8 H8B 0.956(16) . ?
C9 H9A 0.969(18) . ?
C9 H9B 0.985(19) . ?
C9 H9C 0.984(16) . ?
C10 H10A 0.987(19) . ?
C10 H10B 1.006(19) . ?
C10 H10C 0.999(19) . ?
C11 C12 1.5051(14) . ?
C12 C13 1.4194(16) . ?
C12 C21 1.3790(15) . ?
C13 H13 0.946(16) . ?
C13 C14 1.3687(16) . ?
C14 H14 0.940(17) . ?
C14 C15 1.4191(16) . ?
C15 C16 1.4212(16) . ?
C15 C20 1.4183(17) . ?
C16 H16 0.951(17) . ?
C16 C17 1.3699(19) . ?
C17 H17 0.96(2) . ?
C17 C18 1.406(2) . ?
C18 H18 0.990(19) . ?
C18 C19 1.3705(18) . ?
C19 H19 0.971(18) . ?
C19 C20 1.4216(15) . ?
C20 C21 1.4162(15) . ?
C21 H21 0.947(16) . ?
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 124.70(12) . . . . ?
O1 C1 C7 C6 -99.59(12) . . . . ?
O1 C1 C7 C10 25.57(14) . . . . ?
O2 C11 C12 C13 -158.41(11) . . . . ?
O2 C11 C12 C21 22.18(15) . . . . ?
C1 C2 C3 C4 -35.59(13) . . . . ?
C1 C2 C3 C8 64.02(13) . . . . ?
C2 C1 C7 C6 80.46(11) . . . . ?
C2 C1 C7 C10 -154.38(10) . . . . ?
C2 C3 C4 C5 97.67(10) . . . . ?
C2 C3 C8 C5 -94.93(10) . . . . ?
C3 C4 C5 C6 -96.36(10) . . . . ?
C3 C4 C5 C8 19.61(8) . . . . ?
C3 C4 C5 C11 138.13(9) . . . . ?
C4 C3 C8 C5 19.69(8) . . . . ?
C4 C5 C6 C7 66.56(11) . . . . ?
C4 C5 C6 C9 -60.91(11) . . . . ?
C4 C5 C8 C3 -19.56(8) . . . . ?
C4 C5 C11 O2 13.48(14) . . . . ?
C4 C5 C11 C12 -169.76(9) . . . . ?
C5 C6 C7 C1 -54.25(11) . . . . ?
C5 C6 C7 C10 -179.52(9) . . . . ?
C5 C11 C12 C13 24.80(14) . . . . ?
C5 C11 C12 C21 -154.60(10) . . . . ?
C6 C5 C8 C3 96.84(9) . . . . ?
C6 C5 C11 O2 -115.68(11) . . . . ?
C6 C5 C11 C12 61.09(11) . . . . ?
C7 C1 C2 C3 -55.35(13) . . . . ?
C8 C3 C4 C5 -19.83(8) . . . . ?
C8 C5 C6 C7 -32.38(12) . . . . ?
C8 C5 C6 C9 -159.85(9) . . . . ?
C8 C5 C11 O2 113.03(12) . . . . ?
C8 C5 C11 C12 -70.20(12) . . . . ?
C9 C6 C7 C1 72.25(11) . . . . ?
C9 C6 C7 C10 -53.02(12) . . . . ?
C11 C5 C6 C7 -165.01(8) . . . . ?
C11 C5 C6 C9 67.51(10) . . . . ?
C11 C5 C8 C3 -134.96(9) . . . . ?
C11 C12 C13 C14 179.82(9) . . . . ?
C11 C12 C21 C20 177.59(9) . . . . ?
C12 C13 C14 C15 2.63(16) . . . . ?
C13 C12 C21 C20 -1.84(15) . . . . ?
C13 C14 C15 C16 177.19(10) . . . . ?
C13 C14 C15 C20 -1.85(16) . . . . ?
C14 C15 C16 C17 -177.19(11) . . . . ?
C14 C15 C20 C19 178.42(10) . . . . ?
C14 C15 C20 C21 -0.73(15) . . . . ?
C15 C16 C17 C18 -1.24(18) . . . . ?
C15 C20 C21 C12 2.57(15) . . . . ?
C16 C15 C20 C19 -0.65(15) . . . . ?
C16 C15 C20 C21 -179.80(9) . . . . ?
C16 C17 C18 C19 -0.63(19) . . . . ?
C17 C18 C19 C20 1.83(18) . . . . ?
C18 C19 C20 C15 -1.18(16) . . . . ?
C18 C19 C20 C21 177.95(10) . . . . ?
C19 C20 C21 C12 -176.55(10) . . . . ?
C20 C15 C16 C17 1.85(16) . . . . ?
C21 C12 C13 C14 -0.78(15) . . . . ?
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
-1.0000 2.0000 -2.0000 -0.2684 0.3190 -0.3455
2.0000 -2.0000 1.0000 0.1950 -0.2413 0.4269
1.0000 -2.0000 2.0000 0.2684 -0.3190 0.3455
2.0000 -0.0000 -1.0000 -0.1379 0.0484 0.1323
-2.0000 -1.0000 1.0000 0.2954 -0.0862 0.0456
1.0000 2.0000 -1.0000 -0.3884 0.1533 -0.2744
-1.0000 2.0000 -0.0000 -0.2505 0.1049 -0.4066
1.0000 -0.0000 0.0000 -0.0645 -0.0293 0.0508
-1.0000 0.0000 -0.0000 0.0645 0.0293 -0.0508
-2.0000 -1.0000 -1.0000 0.2774 0.1280 0.1068
1.0000 -2.0000 -2.0000 0.2326 0.1093 0.4678
8.6904 2.4170 2.0457 -0.9225 -0.3827 -0.0507
-11.3654 0.7036 0.9129 0.6300 0.2622 -0.7310
-0.0000 1.0000 1.0000 -0.1485 -0.0693 -0.2085
-2.0000 -0.0000 -1.0000 0.1200 0.1657 -0.0711
2.0000 0.0000 1.0000 -0.1200 -0.1657 0.0711
0.0000 -0.0000 -1.0000 -0.0090 0.1071 0.0306
-0.0000 0.0000 1.0000 0.0090 -0.1071 -0.0306
4.5006 -1.9275 6.7544 0.0739 -0.9280 0.3651
-1.7599 -2.4400 7.2565 0.5627 -0.8175 0.1226
-10.5283 0.0667 4.4991 0.7085 -0.1704 -0.6849
-10.0519 -1.2393 4.2925 0.8816 -0.2116 -0.4220
-11.4058 -0.5546 1.4829 0.8359 0.1548 -0.5266
-11.4765 -0.0952 1.7784 0.7707 0.1426 -0.6210
1.0000 -0.0000 -2.0000 -0.0824 0.1848 0.1120
