#------------------------------------------------------------------------------
#$Date: 2021-06-05 20:54:47 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/06/1560602.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_1560602
loop_
_publ_author_name
'Zheng, Haifeng'
'Wang, Rui'
'Wang, Kan'
'Wherritt, Daniel'
'Arman, Hadi'
'Doyle, Michael P.'
_publ_section_title
;
 Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of
 donor--acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by
 Brønsted acid catalysis
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4819
_journal_page_last               4824
_journal_paper_doi               10.1039/D1SC00158B
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H23 F O5'
_chemical_formula_sum            'C29 H23 F O5'
_chemical_formula_weight         470.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-15
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-06-16 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.001(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9631(3)
_cell_length_b                   9.1494(2)
_cell_length_c                   13.3605(4)
_cell_measurement_reflns_used    6038
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3640
_cell_measurement_theta_min      4.5230
_cell_volume                     1191.28(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  -1.00   0.50    0.38    --  -46.62 109.00 122.00  160
  2  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  60.00   70
  3  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00  90.00   70
  4  ω    -82.00 -15.00   0.50    1.52    --  -88.50 109.00 122.00  134
  5  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -30.00   70
  6  ω    -51.00 -16.00   0.50    1.52    --  -88.50  45.00 -60.00   70
  7  ω   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00-150.00   72
  8  ω   -120.00 -48.00   0.50    0.38    --  -46.62 -37.00-120.00  144
  9  ω   -119.00 -87.00   0.50    0.38    --  -46.62-125.00-120.00   64
 10  ω   -119.00 -83.00   0.50    0.38    --  -46.62 -57.00   0.00   72
 11  ω   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00   0.00  176
 12  ω     22.00  87.00   0.50    0.38    --   46.62-109.00  26.00  130
 13  ω     34.00 108.00   0.50    1.52    --  106.69-109.00  26.00  148
 14  ω     34.00 111.00   0.50    1.52    --  106.69-125.00   0.00  154
 15  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00   0.00  134
 16  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00 120.00   74
 17  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00  60.00  134
 18  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00   0.00   74
 19  ω     83.00 120.00   0.50    0.38    --   46.62  57.00-150.00   74
 20  ω     83.00 120.00   0.50    0.38    --   46.62  57.00-180.00   74
 21  ω     83.00 120.00   0.50    0.38    --   46.62  57.00 -90.00   74
 22  ω     95.00 178.00   0.50    1.52    --  106.69 125.00-150.00  166
 23  ω    104.00 178.00   0.50    1.52    --  106.69 109.00 122.00  148
 24  ω     34.00 101.00   0.50    1.52    --  106.69 -77.00-180.00  134
 25  ω     34.00  71.00   0.50    1.52    --  106.69 -61.00-180.00   74
 26  ω   -119.00 -87.00   0.50    0.38    --  -46.62-125.00  60.00   64
 27  ω   -120.00 -32.00   0.50    0.38    --  -46.62 -37.00  90.00  176
 28  ω   -160.00 -82.00   0.50    1.52    --  -88.50-109.00  26.00  156
 29  ω   -160.00-100.00   0.50    1.52    --  -88.50 -94.00  60.00  120
 30  ω   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  90.00  118
 31  ω   -160.00-101.00   0.50    1.52    --  -88.50 -77.00  60.00  118
;
_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      0.1513375000
_diffrn_orient_matrix_UB_12      -0.0430721000
_diffrn_orient_matrix_UB_13      0.0388238000
_diffrn_orient_matrix_UB_21      -0.0343531000
_diffrn_orient_matrix_UB_22      -0.1585794000
_diffrn_orient_matrix_UB_23      -0.0352750000
_diffrn_orient_matrix_UB_31      0.0303977000
_diffrn_orient_matrix_UB_32      0.0366671000
_diffrn_orient_matrix_UB_33      -0.1055404000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14112
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.406
_diffrn_reflns_theta_min         3.382
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0475
_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)+(0.0500P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3887
_reflns_number_total             4208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00158b2.cif
_cod_data_source_block           hpd119b
_cod_depositor_comments
'Adding full bibliography for 1560602--1560604.cif.'
_cod_database_code               1560602
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     HF-0610
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(3)
 0.3(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C28(H28), C5(H5), C27(H27), C15(H15), C19(H19), C8(H8), C25(H25),
 C7(H7), C24(H24), C17(H17), C16(H16), C18(H18)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.654
_oxdiff_exptl_absorpt_empirical_full_min 0.732
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
F1 F 0.3438(2) 0.0513(2) 0.45385(16) 0.0364(5) Uani 1 1 d . . . . .
O1 O 0.4387(3) 0.3133(3) 0.94540(17) 0.0300(6) Uani 1 1 d . . . . .
H1 H 0.517339 0.281758 0.960852 0.045 Uiso 1 1 calc R U . . .
O5 O 0.6546(3) 0.2076(3) 0.92387(17) 0.0337(6) Uani 1 1 d . . . . .
O3 O 0.3045(3) 0.8279(3) 0.84249(19) 0.0344(6) Uani 1 1 d . . . . .
O4 O 0.4692(3) 0.8573(3) 0.7523(2) 0.0353(6) Uani 1 1 d . . . . .
O2 O 0.0765(3) 0.5978(4) 0.6645(2) 0.0436(7) Uani 1 1 d . . . . .
C22 C 0.6204(4) 0.2285(4) 0.8248(3) 0.0282(8) Uani 1 1 d . . . . .
C14 C 0.0068(4) 0.6239(4) 0.8211(3) 0.0266(7) Uani 1 1 d . . . . .
C20 C 0.3860(4) 0.7808(4) 0.7808(3) 0.0282(8) Uani 1 1 d . . . . .
C3 C 0.2569(4) 0.5486(4) 0.8074(3) 0.0255(7) Uani 1 1 d . . . . .
H3 H 0.276046 0.581299 0.878834 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4202(4) 0.1687(4) 0.6113(3) 0.0261(7) Uani 1 1 d . . . . .
H10 H 0.446629 0.078867 0.641558 0.031 Uiso 1 1 calc R U . . .
C1 C 0.4026(4) 0.3247(4) 0.8468(2) 0.0261(7) Uani 1 1 d . . . . .
C9 C 0.3640(4) 0.1784(4) 0.5084(3) 0.0287(7) Uani 1 1 d . . . . .
C12 C 0.4911(4) 0.2870(4) 0.7816(3) 0.0263(7) Uani 1 1 d . . . . .
C28 C 0.7508(4) 0.2667(4) 0.6849(3) 0.0293(8) Uani 1 1 d . . . . .
H28 H 0.695865 0.347187 0.662101 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4368(3) 0.2978(4) 0.6696(2) 0.0242(7) Uani 1 1 d . . . . .
C4 C 0.3563(4) 0.6239(4) 0.7524(3) 0.0261(7) Uani 1 1 d . . . . .
C13 C 0.1099(4) 0.5931(4) 0.7574(3) 0.0280(7) Uani 1 1 d . . . . .
C6 C 0.3958(3) 0.4322(4) 0.6213(3) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.4093(4) 0.5749(4) 0.6748(3) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.464257 0.642172 0.649926 0.032 Uiso 1 1 calc R U . . .
C23 C 0.7258(4) 0.1851(4) 0.7678(3) 0.0281(7) Uani 1 1 d . . . . .
C27 C 0.8551(4) 0.2298(5) 0.6369(3) 0.0345(8) Uani 1 1 d . . . . .
H27 H 0.872563 0.288696 0.584355 0.041 Uiso 1 1 calc R U . . .
C15 C -0.1306(4) 0.6146(4) 0.7749(3) 0.0335(8) Uani 1 1 d . . . . .
H15 H -0.155466 0.583784 0.707286 0.040 Uiso 1 1 calc R U . . .
C19 C 0.0439(4) 0.6674(5) 0.9235(3) 0.0367(9) Uani 1 1 d . . . . .
H19 H 0.135888 0.671582 0.956099 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2601(4) 0.3797(4) 0.8059(3) 0.0264(7) Uani 1 1 d . . . . .
H2A H 0.198635 0.341501 0.847074 0.032 Uiso 1 1 calc R U . . .
H2B H 0.228623 0.345204 0.736264 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3268(4) 0.3081(4) 0.4584(3) 0.0312(8) Uani 1 1 d . . . . .
H8 H 0.290979 0.310505 0.388346 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9109(4) 0.0238(4) 0.7483(3) 0.0368(9) Uani 1 1 d . . . . .
H25 H 0.964183 -0.058386 0.769573 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9356(4) 0.1054(4) 0.6654(3) 0.0348(9) Uani 1 1 d . . . . .
C7 C 0.3443(4) 0.4342(4) 0.5158(3) 0.0308(8) Uani 1 1 d . . . . .
H7 H 0.321207 0.523318 0.483306 0.037 Uiso 1 1 calc R U . . .
C24 C 0.8091(4) 0.0629(4) 0.7992(3) 0.0326(8) Uani 1 1 d . . . . .
H24 H 0.795523 0.007745 0.854777 0.039 Uiso 1 1 calc R U . . .
C17 C -0.1946(4) 0.6957(5) 0.9284(3) 0.0404(10) Uani 1 1 d . . . . .
H17 H -0.261956 0.720433 0.964241 0.049 Uiso 1 1 calc R U . . .
C16 C -0.2315(4) 0.6504(5) 0.8275(3) 0.0416(10) Uani 1 1 d . . . . .
H16 H -0.323559 0.644128 0.795359 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0572(4) 0.7040(6) 0.9757(3) 0.0432(10) Uani 1 1 d . . . . .
H18 H -0.032786 0.734655 1.043465 0.052 Uiso 1 1 calc R U . . .
C21 C 0.3212(5) 0.9794(4) 0.8732(3) 0.0399(9) Uani 1 1 d . . . . .
H21A H 0.293786 1.040858 0.814230 0.060 Uiso 1 1 calc R U . . .
H21B H 0.415709 0.997696 0.903740 0.060 Uiso 1 1 calc R U . . .
H21C H 0.265234 1.000136 0.921858 0.060 Uiso 1 1 calc R U . . .
C29 C 1.0431(4) 0.0596(6) 0.6081(4) 0.0481(11) Uani 1 1 d . . . . .
H29A H 1.000196 0.036338 0.538754 0.072 Uiso 1 1 calc R U . . .
H29B H 1.090524 -0.024889 0.640331 0.072 Uiso 1 1 calc R U . . .
H29C H 1.107249 0.137955 0.608530 0.072 Uiso 1 1 calc R 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'
F F 0.0727 0.0534 '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
2 -1 -8 0.0820
0 -6 -1 0.0527
-2 1 8 0.0344
0 6 0 0.0504
6 0 2 0.0131
-3 -1 8 0.0450
-6 0 -2 0.0075
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 H1 109.5 . . ?
C20 O3 C21 115.7(3) . . ?
O5 C22 C12 119.6(3) . . ?
O5 C22 C23 114.8(3) . . ?
C12 C22 C23 125.6(3) . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 C19 119.3(3) . . ?
C19 C14 C13 122.6(3) . . ?
O3 C20 C4 110.5(3) . . ?
O4 C20 O3 123.4(3) . . ?
O4 C20 C4 126.0(3) . . ?
C4 C3 H3 108.6 . . ?
C4 C3 C13 109.2(3) . . ?
C4 C3 C2 115.5(3) . . ?
C13 C3 H3 108.6 . . ?
C13 C3 C2 106.3(3) . . ?
C2 C3 H3 108.6 . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
O1 C1 C12 122.2(3) . . ?
O1 C1 C2 116.1(3) . . ?
C12 C1 C2 121.7(3) . . ?
F1 C9 C10 117.6(3) . . ?
F1 C9 C8 118.8(3) . . ?
C8 C9 C10 123.7(3) . . ?
C22 C12 C1 118.7(3) . . ?
C22 C12 C11 123.4(3) . . ?
C1 C12 C11 117.7(3) . . ?
C23 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C23 121.0(3) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C6 119.3(3) . . ?
C6 C11 C12 122.0(3) . . ?
C20 C4 C3 115.2(3) . . ?
C5 C4 C20 115.5(3) . . ?
C5 C4 C3 128.9(3) . . ?
O2 C13 C14 120.0(3) . . ?
O2 C13 C3 119.2(3) . . ?
C14 C13 C3 120.7(3) . . ?
C11 C6 C5 124.0(3) . . ?
C7 C6 C11 119.0(3) . . ?
C7 C6 C5 116.9(3) . . ?
C4 C5 C6 131.3(3) . . ?
C4 C5 H5 114.3 . . ?
C6 C5 H5 114.3 . . ?
C28 C23 C22 121.8(3) . . ?
C28 C23 C24 118.1(3) . . ?
C24 C23 C22 120.0(3) . . ?
C28 C27 H27 119.3 . . ?
C28 C27 C26 121.4(4) . . ?
C26 C27 H27 119.3 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.4(4) . . ?
C18 C19 H19 120.3 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 C3 110.6(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.6(3) . . ?
C7 C8 H8 121.2 . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.3(4) . . ?
C27 C26 C29 121.2(4) . . ?
C25 C26 C27 117.7(3) . . ?
C25 C26 C29 121.1(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.0 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(4) . . ?
C25 C24 H24 119.7 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
F1 C9 1.365(4) . ?
O1 H1 0.8200 . ?
O1 C1 1.296(4) . ?
O5 C22 1.311(4) . ?
O3 C20 1.342(4) . ?
O3 C21 1.445(5) . ?
O4 C20 1.205(4) . ?
O2 C13 1.218(4) . ?
C22 C12 1.404(5) . ?
C22 C23 1.474(5) . ?
C14 C13 1.490(5) . ?
C14 C15 1.382(5) . ?
C14 C19 1.399(5) . ?
C20 C4 1.499(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.517(5) . ?
C3 C13 1.533(5) . ?
C3 C2 1.546(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.375(5) . ?
C10 C11 1.406(5) . ?
C1 C12 1.406(5) . ?
C1 C2 1.497(5) . ?
C9 C8 1.374(5) . ?
C12 C11 1.484(5) . ?
C28 H28 0.9300 . ?
C28 C23 1.400(5) . ?
C28 C27 1.372(5) . ?
C11 C6 1.409(5) . ?
C4 C5 1.334(5) . ?
C6 C5 1.482(5) . ?
C6 C7 1.397(5) . ?
C5 H5 0.9300 . ?
C23 C24 1.404(5) . ?
C27 H27 0.9300 . ?
C27 C26 1.399(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.381(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8 0.9300 . ?
C8 C7 1.376(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.399(6) . ?
C25 C24 1.381(6) . ?
C26 C29 1.500(5) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.385(6) . ?
C17 C18 1.386(6) . ?
C16 H16 0.9300 . ?
C18 H18 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
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
F1 C9 C8 C7 178.1(3) . . . . ?
O1 C1 C12 C22 3.1(5) . . . . ?
O1 C1 C12 C11 177.2(3) . . . . ?
O1 C1 C2 C3 84.2(4) . . . . ?
O5 C22 C12 C1 1.4(5) . . . . ?
O5 C22 C12 C11 -172.4(3) . . . . ?
O5 C22 C23 C28 -141.5(4) . . . . ?
O5 C22 C23 C24 35.4(5) . . . . ?
O3 C20 C4 C3 -7.0(4) . . . . ?
O3 C20 C4 C5 166.2(3) . . . . ?
O4 C20 C4 C3 174.0(3) . . . . ?
O4 C20 C4 C5 -12.8(5) . . . . ?
C22 C12 C11 C10 60.2(5) . . . . ?
C22 C12 C11 C6 -122.8(4) . . . . ?
C22 C23 C24 C25 -178.0(4) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C14 C19 C18 C17 1.1(7) . . . . ?
C20 C4 C5 C6 -175.8(3) . . . . ?
C3 C4 C5 C6 -3.7(6) . . . . ?
C10 C9 C8 C7 -1.5(6) . . . . ?
C10 C11 C6 C5 -179.5(3) . . . . ?
C10 C11 C6 C7 -2.4(5) . . . . ?
C1 C12 C11 C10 -113.6(4) . . . . ?
C1 C12 C11 C6 63.4(4) . . . . ?
C9 C10 C11 C12 177.1(3) . . . . ?
C9 C10 C11 C6 0.0(5) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?
C12 C22 C23 C28 39.0(6) . . . . ?
C12 C22 C23 C24 -144.1(4) . . . . ?
C12 C1 C2 C3 -96.3(4) . . . . ?
C12 C11 C6 C5 3.5(5) . . . . ?
C12 C11 C6 C7 -179.4(3) . . . . ?
C28 C23 C24 C25 -1.0(5) . . . . ?
C28 C27 C26 C25 -3.3(6) . . . . ?
C28 C27 C26 C29 175.7(4) . . . . ?
C11 C10 C9 F1 -177.5(3) . . . . ?
C11 C10 C9 C8 2.1(5) . . . . ?
C11 C6 C5 C4 -60.3(5) . . . . ?
C11 C6 C7 C8 3.0(5) . . . . ?
C4 C3 C13 O2 43.0(4) . . . . ?
C4 C3 C13 C14 -139.8(3) . . . . ?
C4 C3 C2 C1 54.9(4) . . . . ?
C13 C14 C15 C16 -176.0(4) . . . . ?
C13 C14 C19 C18 175.4(4) . . . . ?
C13 C3 C4 C20 78.9(4) . . . . ?
C13 C3 C4 C5 -93.1(4) . . . . ?
C13 C3 C2 C1 176.1(3) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C23 C22 C12 C1 -179.2(3) . . . . ?
C23 C22 C12 C11 7.1(6) . . . . ?
C23 C28 C27 C26 3.3(6) . . . . ?
C27 C28 C23 C22 175.9(3) . . . . ?
C27 C28 C23 C24 -1.1(5) . . . . ?
C15 C14 C13 O2 18.7(5) . . . . ?
C15 C14 C13 C3 -158.5(3) . . . . ?
C15 C14 C19 C18 -1.7(6) . . . . ?
C19 C14 C13 O2 -158.5(4) . . . . ?
C19 C14 C13 C3 24.3(5) . . . . ?
C19 C14 C15 C16 1.3(6) . . . . ?
C2 C3 C4 C20 -161.4(3) . . . . ?
C2 C3 C4 C5 26.5(5) . . . . ?
C2 C3 C13 O2 -82.2(4) . . . . ?
C2 C3 C13 C14 95.0(4) . . . . ?
C2 C1 C12 C22 -176.4(3) . . . . ?
C2 C1 C12 C11 -2.3(5) . . . . ?
C26 C25 C24 C23 1.0(6) . . . . ?
C7 C6 C5 C4 122.5(4) . . . . ?
C24 C25 C26 C27 1.1(6) . . . . ?
C24 C25 C26 C29 -177.8(4) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C18 C17 C16 C15 -0.3(7) . . . . ?
C21 O3 C20 O4 0.5(5) . . . . ?
C21 O3 C20 C4 -178.5(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(3)
2 0.3(3)
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
2.4417 -1.2390 -8.3326 0.0994 0.4065 0.9082
0.0917 -5.9034 -0.9309 0.2320 0.9658 -0.1154
-2.4631 1.0512 8.3845 -0.0925 -0.3778 -0.9212
0.3045 5.9291 -0.3974 -0.2247 -0.9367 0.2686
5.9270 -0.1935 1.7243 0.9723 -0.2337 -0.0089
-3.0366 -1.2930 8.1111 -0.0890 0.0232 -0.9958
-5.9270 0.1935 -1.7243 -0.9723 0.2337 0.0089
