#------------------------------------------------------------------------------
#$Date: 2022-04-13 01:41:34 +0300 (Wed, 13 Apr 2022) $
#$Revision: 274501 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244772.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_7244772
loop_
_publ_author_name
'Matsuhashi, Chihiro'
'Oyama, Hironaga'
'Uekusa, Hidehiro'
'Sato-Tomita, Ayana'
'Ichiyanagi, Kouhei'
'Maki, Shojiro A.'
'Hirano, Takashi'
_publ_section_title
;
 Crystalline-state chemiluminescence reactions of two-fluorophore-linked
 adamantylideneadamantane 1,2-dioxetane isomers accompanied by
 solid-to-solid phase transitions
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00266C
_journal_year                    2022
_chemical_formula_moiety         'C34 H28 F3 N O6'
_chemical_formula_sum            'C34 H28 F3 N O6'
_chemical_formula_weight         603.57
_chemical_melting_point          468.5(5)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                108.781(7)
_cell_angle_beta                 101.858(6)
_cell_angle_gamma                105.672(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4930(4)
_cell_length_b                   13.8284(10)
_cell_length_c                   15.4815(13)
_cell_measurement_reflns_used    5323
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      29.9620
_cell_measurement_theta_min      2.6650
_cell_volume                     1385.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00 -63.00   0.50   80.77    --   -4.30  45.00  60.00   54
  2  ω    -92.00  84.00   0.50   80.77    --   -4.30  45.00 150.00  352
  3  ω     38.00  65.00   0.50   80.77    --   -4.30  45.00  60.00   54
  4  ω    -24.00  46.00   0.50   80.77    --   -4.30  45.00   0.00  140
  5  ω    -37.00 -10.00   0.50   80.77    --   -4.30  45.00  60.00   54
  6  ω    -41.00 -14.00   0.50   80.77    --    4.30  45.00  30.00   54
  7  ω    -84.00  90.00   0.50   80.77    --    4.30  45.00  90.00  348
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RINC): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1015902000
_diffrn_orient_matrix_UB_12      0.0302602000
_diffrn_orient_matrix_UB_13      0.0235582000
_diffrn_orient_matrix_UB_21      0.0167139000
_diffrn_orient_matrix_UB_22      -0.0494607000
_diffrn_orient_matrix_UB_23      -0.0057388000
_diffrn_orient_matrix_UB_31      0.0132465000
_diffrn_orient_matrix_UB_32      -0.0042980000
_diffrn_orient_matrix_UB_33      -0.0449736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.357
_diffrn_reflns_theta_min         2.627
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-Hexane / dichloromethane'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0645
_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)+(0.0981P)²+0.4513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5449
_reflns_number_total             6970
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00266c4.cif
_cod_data_source_block           cm-ii-108-2_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '468-469' was changed to
'468.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1384.96(19)
_cod_database_code               7244772
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C34H28F3NO6
_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   0.990
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Sof(F2B)=Sof(F3A)=Sof(F1B)=1-FVAR(1)
 Sof(F3B)=Sof(F2A)=Sof(F1A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C29(H29), C27(H27), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C26(H26A,H26B), C23(H23A,H23B), C31(H31A,H31B), C33(H33A,
 H33B), C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C3(H3), C6(H6), C12(H12), C14(H14), C7(H7), C21(H21),
 C20(H20), C15(H15)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 1.434
_oxdiff_exptl_absorpt_empirical_full_min 0.726
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O4 O 1.21228(19) 0.39879(10) 0.86317(9) 0.0290(3) Uani 1 1 d . . . . .
O3 O 1.36256(19) 0.17348(10) 0.95292(10) 0.0305(3) Uani 1 1 d . . . . .
O5 O 1.2599(2) 0.52376(11) 1.00962(9) 0.0309(3) Uani 1 1 d . . . . .
O6 O 1.1813(2) 0.82983(11) 0.82793(11) 0.0378(4) Uani 1 1 d . . . . .
O2 O -0.15379(19) -0.01606(11) 0.56699(10) 0.0351(3) Uani 1 1 d . . . . .
O1 O 0.33230(19) 0.32167(11) 0.67807(11) 0.0366(3) Uani 1 1 d . . . . .
F3B F -0.3952(10) 0.4049(7) 0.4118(7) 0.0482(18) Uani 0.51(3) 1 d . . P A 1
N1 N 0.0502(2) 0.16455(13) 0.61330(11) 0.0259(3) Uani 1 1 d . . . . .
F2A F -0.601(3) 0.2436(9) 0.3413(12) 0.109(5) Uani 0.51(3) 1 d . . P A 1
C5 C -0.0827(3) 0.20251(15) 0.56588(12) 0.0262(4) Uani 1 1 d . . . . .
C30 C 1.2355(3) 0.58304(14) 0.80779(13) 0.0243(4) Uani 1 1 d . . . . .
H30A H 1.246826 0.518116 0.761384 0.029 Uiso 1 1 calc R U . . .
H30B H 1.368723 0.633546 0.851075 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7777(3) 0.10812(14) 0.81254(12) 0.0238(4) Uani 1 1 d . . . . .
C24 C 1.2025(2) 0.49125(14) 0.92282(12) 0.0229(3) Uani 1 1 d . . . . .
C4 C -0.0164(3) 0.27664(16) 0.52681(13) 0.0284(4) Uani 1 1 d . . . . .
H4 H 0.117690 0.302244 0.531356 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5724(3) 0.09023(14) 0.76295(12) 0.0238(4) Uani 1 1 d . . . . .
C19 C 1.1686(3) 0.14606(14) 0.90673(12) 0.0252(4) Uani 1 1 d . . . . .
C17 C 0.9294(3) 0.20583(14) 0.83386(12) 0.0238(4) Uani 1 1 d . . . . .
H17 H 0.898670 0.260122 0.815422 0.029 Uiso 1 1 calc R U . . .
C18 C 1.1222(3) 0.22647(14) 0.88070(12) 0.0240(4) Uani 1 1 d . . . . .
C25 C 1.1101(2) 0.54733(13) 0.86710(12) 0.0215(3) Uani 1 1 d . . . . .
C10 C 0.1875(3) 0.05325(14) 0.66452(12) 0.0253(4) Uani 1 1 d . . . . .
C11 C 0.3343(3) 0.15395(15) 0.69512(13) 0.0259(4) Uani 1 1 d . . . . .
F1A F -0.589(2) 0.3489(12) 0.4792(11) 0.072(3) Uani 0.51(3) 1 d . . P A 1
C28 C 1.1159(3) 0.73752(14) 0.82342(13) 0.0258(4) Uani 1 1 d . . . . .
C29 C 1.1391(3) 0.64109(15) 0.75306(13) 0.0254(4) Uani 1 1 d . . . . .
H29 H 1.220715 0.665997 0.715199 0.030 Uiso 1 1 calc R U . . .
C26 C 1.0962(3) 0.64892(14) 0.93909(13) 0.0253(4) Uani 1 1 d . . . . .
H26A H 1.228913 0.699922 0.982650 0.030 Uiso 1 1 calc R U . . .
H26B H 1.018310 0.627044 0.978725 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2511(3) 0.22778(15) 0.66421(13) 0.0278(4) Uani 1 1 d . . . . .
C3 C -0.1461(3) 0.31372(16) 0.48087(13) 0.0292(4) Uani 1 1 d . . . . .
H3 H -0.100538 0.364930 0.454268 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0043(3) 0.05682(15) 0.61000(12) 0.0266(4) Uani 1 1 d . . . . .
C6 C -0.2795(3) 0.16423(16) 0.55854(14) 0.0305(4) Uani 1 1 d . . . . .
H6 H -0.325349 0.113284 0.585340 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5246(3) 0.17446(15) 0.74450(13) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.622465 0.244876 0.765845 0.032 Uiso 1 1 calc R U . . .
C2 C -0.3418(3) 0.27591(16) 0.47390(13) 0.0300(4) Uani 1 1 d . . . . .
C23 C 1.2846(3) 0.33229(15) 0.90555(14) 0.0293(4) Uani 1 1 d . . . . .
H23A H 1.339378 0.372586 0.976403 0.035 Uiso 1 1 calc R U . . .
H23B H 1.390585 0.316757 0.881321 0.035 Uiso 1 1 calc R U . . .
C27 C 0.9989(3) 0.70679(15) 0.88487(13) 0.0289(4) Uani 1 1 d . . . . .
H27 H 0.990850 0.773656 0.931653 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4198(3) -0.01088(15) 0.73299(13) 0.0285(4) Uani 1 1 d . . . . .
H14 H 0.449195 -0.068270 0.746330 0.034 Uiso 1 1 calc R U . . .
C7 C -0.4080(3) 0.20086(17) 0.51193(14) 0.0326(4) Uani 1 1 d . . . . .
H7 H -0.542639 0.174142 0.506091 0.039 Uiso 1 1 calc R U . . .
C21 C 0.8302(3) 0.03015(15) 0.83909(14) 0.0322(4) Uani 1 1 d . . . . .
H21 H 0.730933 -0.037617 0.824800 0.039 Uiso 1 1 calc R U . . .
C31 C 0.9040(3) 0.46832(15) 0.79762(14) 0.0276(4) Uani 1 1 d . . . . .
H31A H 0.914024 0.403459 0.750483 0.033 Uiso 1 1 calc R U . . .
H31B H 0.822169 0.442830 0.834383 0.033 Uiso 1 1 calc R U . . .
C20 C 1.0222(3) 0.04789(15) 0.88564(14) 0.0309(4) Uani 1 1 d . . . . .
H20 H 1.053191 -0.006979 0.902992 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2271(3) -0.02995(15) 0.68449(13) 0.0301(4) Uani 1 1 d . . . . .
H15 H 0.125945 -0.098549 0.665786 0.036 Uiso 1 1 calc R U . . .
C32 C 0.8082(3) 0.52695(15) 0.74431(14) 0.0310(4) Uani 1 1 d . . . . .
H32 H 0.674222 0.475495 0.700237 0.037 Uiso 1 1 calc R U . . .
C33 C 0.9313(3) 0.56285(15) 0.68530(13) 0.0306(4) Uani 1 1 d . . . . .
H33A H 0.869910 0.600601 0.650662 0.037 Uiso 1 1 calc R U . . .
H33B H 0.938629 0.497882 0.637015 0.037 Uiso 1 1 calc R U . . .
C22 C 1.4181(3) 0.09277(17) 0.97858(15) 0.0367(5) Uani 1 1 d . . . . .
H22A H 1.369763 0.023911 0.921409 0.055 Uiso 1 1 calc R U . . .
H22B H 1.361628 0.080672 1.027655 0.055 Uiso 1 1 calc R U . . .
H22C H 1.561113 0.118417 1.004242 0.055 Uiso 1 1 calc R U . . .
C34 C 0.7926(3) 0.62702(17) 0.81705(16) 0.0345(4) Uani 1 1 d . . . . .
H34A H 0.711722 0.603657 0.855011 0.041 Uiso 1 1 calc R U . . .
H34B H 0.728715 0.664160 0.782701 0.041 Uiso 1 1 calc R U . . .
C1 C -0.4810(3) 0.31501(19) 0.42383(16) 0.0390(5) Uani 1 1 d . . . . .
F2B F -0.5498(12) 0.2510(9) 0.3264(6) 0.0481(18) Uani 0.49(3) 1 d . . P A 2
F3A F -0.4002(14) 0.4140(7) 0.4282(10) 0.085(3) Uani 0.49(3) 1 d . . P A 2
F1B F -0.639(2) 0.305(2) 0.4459(14) 0.095(4) Uani 0.49(3) 1 d . . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
9 0 -15 0.1462
1 -5 21 0.0515
-1 5 -21 0.0724
4 -10 -15 0.1351
-1 -17 14 0.0310
-4 7 16 0.0829
1 18 -14 0.0519
-8 -2 17 0.1371
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
C24 O4 C23 117.78(14) . . ?
C19 O3 C22 117.09(15) . . ?
C8 N1 C5 124.14(16) . . ?
C9 N1 C5 125.01(15) . . ?
C9 N1 C8 110.68(15) . . ?
C4 C5 N1 120.08(16) . . ?
C4 C5 C6 120.06(17) . . ?
C6 C5 N1 119.86(17) . . ?
H30A C30 H30B 108.3 . . ?
C25 C30 H30A 109.8 . . ?
C25 C30 H30B 109.8 . . ?
C25 C30 C29 109.34(14) . . ?
C29 C30 H30A 109.8 . . ?
C29 C30 H30B 109.8 . . ?
C17 C16 C13 120.54(16) . . ?
C21 C16 C13 122.77(17) . . ?
C21 C16 C17 116.69(16) . . ?
O4 C24 C25 111.35(14) . . ?
O5 C24 O4 123.42(16) . . ?
O5 C24 C25 125.22(16) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.97(17) . . ?
C3 C4 H4 120.0 . . ?
C12 C13 C16 120.65(16) . . ?
C12 C13 C14 117.74(16) . . ?
C14 C13 C16 121.61(16) . . ?
O3 C19 C18 114.99(16) . . ?
O3 C19 C20 125.04(16) . . ?
C20 C19 C18 119.97(17) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.54(16) . . ?
C18 C17 H17 118.7 . . ?
C19 C18 C23 118.45(16) . . ?
C17 C18 C19 118.94(17) . . ?
C17 C18 C23 122.61(16) . . ?
C30 C25 C31 108.54(14) . . ?
C24 C25 C30 110.62(14) . . ?
C24 C25 C26 108.49(14) . . ?
C24 C25 C31 110.17(14) . . ?
C26 C25 C30 109.00(14) . . ?
C26 C25 C31 110.01(15) . . ?
C11 C10 C9 108.37(17) . . ?
C15 C10 C11 120.50(17) . . ?
C15 C10 C9 131.11(17) . . ?
C10 C11 C8 109.08(16) . . ?
C12 C11 C10 122.01(18) . . ?
C12 C11 C8 128.90(17) . . ?
O6 C28 C29 123.02(18) . . ?
O6 C28 C27 123.80(17) . . ?
C27 C28 C29 113.16(15) . . ?
C30 C29 H29 110.1 . . ?
C28 C29 C30 109.75(14) . . ?
C28 C29 H29 110.1 . . ?
C28 C29 C33 106.63(15) . . ?
C33 C29 C30 110.15(15) . . ?
C33 C29 H29 110.1 . . ?
C25 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C25 C26 C27 109.96(14) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
O1 C8 N1 125.70(18) . . ?
O1 C8 C11 128.66(17) . . ?
N1 C8 C11 105.64(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.95(19) . . ?
C2 C3 H3 120.0 . . ?
O2 C9 N1 124.78(18) . . ?
O2 C9 C10 128.97(18) . . ?
N1 C9 C10 106.19(14) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.59(19) . . ?
C7 C6 H6 120.2 . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.21(16) . . ?
C11 C12 H12 120.4 . . ?
C3 C2 C1 119.88(19) . . ?
C7 C2 C3 119.94(18) . . ?
C7 C2 C1 120.16(18) . . ?
O4 C23 C18 110.20(14) . . ?
O4 C23 H23A 109.6 . . ?
O4 C23 H23B 109.6 . . ?
C18 C23 H23A 109.6 . . ?
C18 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C28 C27 C26 109.23(15) . . ?
C28 C27 H27 110.2 . . ?
C28 C27 C34 107.44(15) . . ?
C26 C27 H27 110.2 . . ?
C26 C27 C34 109.46(15) . . ?
C34 C27 H27 110.2 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.42(17) . . ?
C15 C14 H14 118.8 . . ?
C6 C7 H7 119.8 . . ?
C2 C7 C6 120.48(18) . . ?
C2 C7 H7 119.8 . . ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.27(18) . . ?
C20 C21 H21 118.9 . . ?
C25 C31 H31A 109.7 . . ?
C25 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
C32 C31 C25 109.90(14) . . ?
C32 C31 H31A 109.7 . . ?
C32 C31 H31B 109.7 . . ?
C19 C20 C21 119.58(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C10 C15 C14 118.05(17) . . ?
C10 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C31 C32 H32 109.3 . . ?
C33 C32 C31 109.51(16) . . ?
C33 C32 H32 109.3 . . ?
C33 C32 C34 109.75(16) . . ?
C34 C32 C31 109.69(16) . . ?
C34 C32 H32 109.3 . . ?
C29 C33 H33A 109.8 . . ?
C29 C33 H33B 109.8 . . ?
C32 C33 C29 109.36(15) . . ?
C32 C33 H33A 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C27 C34 H34A 109.8 . . ?
C27 C34 H34B 109.8 . . ?
C32 C34 C27 109.48(15) . . ?
C32 C34 H34A 109.8 . . ?
C32 C34 H34B 109.8 . . ?
H34A C34 H34B 108.2 . . ?
F3B C1 F1A 101.8(6) . . ?
F3B C1 C2 114.0(4) . . ?
F2A C1 F3B 107.4(9) . . ?
F2A C1 F1A 107.4(9) . . ?
F2A C1 C2 114.9(6) . . ?
F1A C1 C2 110.4(6) . . ?
F2B C1 C2 109.6(4) . . ?
F3A C1 C2 114.0(4) . . ?
F3A C1 F2B 103.1(7) . . ?
F1B C1 C2 115.3(6) . . ?
F1B C1 F2B 102.6(10) . . ?
F1B C1 F3A 110.8(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
O4 C24 1.346(2) . ?
O4 C23 1.443(2) . ?
O3 C19 1.367(2) . ?
O3 C22 1.430(2) . ?
O5 C24 1.209(2) . ?
O6 C28 1.210(2) . ?
O2 C9 1.209(2) . ?
O1 C8 1.201(2) . ?
F3B C1 1.326(7) . ?
N1 C5 1.427(2) . ?
N1 C8 1.418(2) . ?
N1 C9 1.417(3) . ?
F2A C1 1.285(9) . ?
C5 C4 1.382(3) . ?
C5 C6 1.392(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C25 1.538(2) . ?
C30 C29 1.544(2) . ?
C16 C13 1.484(2) . ?
C16 C17 1.399(3) . ?
C16 C21 1.391(3) . ?
C24 C25 1.517(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.390(3) . ?
C13 C12 1.401(3) . ?
C13 C14 1.407(2) . ?
C19 C18 1.400(2) . ?
C19 C20 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(2) . ?
C18 C23 1.501(3) . ?
C25 C26 1.531(2) . ?
C25 C31 1.544(2) . ?
C10 C11 1.381(2) . ?
C10 C9 1.479(3) . ?
C10 C15 1.372(3) . ?
C11 C8 1.482(3) . ?
C11 C12 1.376(2) . ?
F1A C1 1.355(12) . ?
C28 C29 1.504(3) . ?
C28 C27 1.502(3) . ?
C29 H29 1.0000 . ?
C29 C33 1.544(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.541(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C12 H12 0.9500 . ?
C2 C7 1.380(3) . ?
C2 C1 1.491(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C27 H27 1.0000 . ?
C27 C34 1.541(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C7 H7 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.385(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.535(3) . ?
C20 H20 0.9500 . ?
C15 H15 0.9500 . ?
C32 H32 1.0000 . ?
C32 C33 1.524(3) . ?
C32 C34 1.528(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C1 F2B 1.378(9) . ?
C1 F3A 1.312(10) . ?
C1 F1B 1.280(12) . ?
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
O4 C24 C25 C30 -62.73(18) . . . . ?
O4 C24 C25 C26 177.76(14) . . . . ?
O4 C24 C25 C31 57.29(19) . . . . ?
O3 C19 C18 C17 -179.86(15) . . . . ?
O3 C19 C18 C23 -0.2(2) . . . . ?
O3 C19 C20 C21 179.46(18) . . . . ?
O5 C24 C25 C30 117.66(19) . . . . ?
O5 C24 C25 C26 -1.8(2) . . . . ?
O5 C24 C25 C31 -122.32(19) . . . . ?
O6 C28 C29 C30 124.53(18) . . . . ?
O6 C28 C29 C33 -116.18(19) . . . . ?
O6 C28 C27 C26 -124.63(18) . . . . ?
O6 C28 C27 C34 116.72(19) . . . . ?
N1 C5 C4 C3 -179.83(16) . . . . ?
N1 C5 C6 C7 -179.61(16) . . . . ?
C5 N1 C8 O1 3.9(3) . . . . ?
C5 N1 C8 C11 -176.06(16) . . . . ?
C5 N1 C9 O2 -0.5(3) . . . . ?
C5 N1 C9 C10 176.97(15) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C30 C25 C26 C27 60.65(18) . . . . ?
C30 C25 C31 C32 -60.89(19) . . . . ?
C30 C29 C33 C32 59.2(2) . . . . ?
C16 C13 C12 C11 177.51(16) . . . . ?
C16 C13 C14 C15 -178.54(17) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C16 C17 C18 C23 -178.64(17) . . . . ?
C16 C21 C20 C19 -0.2(3) . . . . ?
C24 O4 C23 C18 111.03(17) . . . . ?
C24 C25 C26 C27 -178.82(14) . . . . ?
C24 C25 C31 C32 177.84(15) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C4 C3 C2 C7 -0.5(3) . . . . ?
C4 C3 C2 C1 -179.46(17) . . . . ?
C13 C16 C17 C18 179.36(16) . . . . ?
C13 C16 C21 C20 -179.77(18) . . . . ?
C13 C14 C15 C10 1.0(3) . . . . ?
C19 C18 C23 O4 173.21(16) . . . . ?
C17 C16 C13 C12 -5.8(3) . . . . ?
C17 C16 C13 C14 174.20(17) . . . . ?
C17 C16 C21 C20 0.9(3) . . . . ?
C17 C18 C23 O4 -7.2(2) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C25 C30 C29 C28 57.59(19) . . . . ?
C25 C30 C29 C33 -59.51(19) . . . . ?
C25 C26 C27 C28 -58.16(19) . . . . ?
C25 C26 C27 C34 59.2(2) . . . . ?
C25 C31 C32 C33 61.1(2) . . . . ?
C25 C31 C32 C34 -59.4(2) . . . . ?
C10 C11 C8 O1 179.3(2) . . . . ?
C10 C11 C8 N1 -0.7(2) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C10 C9 O2 175.40(19) . . . . ?
C11 C10 C9 N1 -1.91(19) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C28 C29 C33 C32 -59.86(19) . . . . ?
C28 C27 C34 C32 58.3(2) . . . . ?
C29 C30 C25 C24 -179.27(13) . . . . ?
C29 C30 C25 C26 -60.06(18) . . . . ?
C29 C30 C25 C31 59.75(18) . . . . ?
C29 C28 C27 C26 57.10(19) . . . . ?
C29 C28 C27 C34 -61.55(19) . . . . ?
C26 C25 C31 C32 58.3(2) . . . . ?
C26 C27 C34 C32 -60.2(2) . . . . ?
C8 N1 C5 C4 31.2(3) . . . . ?
C8 N1 C5 C6 -149.22(18) . . . . ?
C8 N1 C9 O2 -176.00(18) . . . . ?
C8 N1 C9 C10 1.46(19) . . . . ?
C8 C11 C12 C13 -177.40(18) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C3 C2 C1 F3B -16.8(5) . . . . ?
C3 C2 C1 F2A 107.8(15) . . . . ?
C3 C2 C1 F1A -130.6(7) . . . . ?
C3 C2 C1 F2B 85.8(4) . . . . ?
C3 C2 C1 F3A -29.1(8) . . . . ?
C3 C2 C1 F1B -159.0(13) . . . . ?
C9 N1 C5 C4 -143.77(18) . . . . ?
C9 N1 C5 C6 35.9(3) . . . . ?
C9 N1 C8 O1 179.51(19) . . . . ?
C9 N1 C8 C11 -0.5(2) . . . . ?
C9 C10 C11 C8 1.6(2) . . . . ?
C9 C10 C11 C12 -177.21(17) . . . . ?
C9 C10 C15 C14 175.81(18) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C12 C11 C8 O1 -2.0(3) . . . . ?
C12 C11 C8 N1 178.00(18) . . . . ?
C23 O4 C24 O5 3.8(2) . . . . ?
C23 O4 C24 C25 -175.84(14) . . . . ?
C27 C28 C29 C30 -57.19(19) . . . . ?
C27 C28 C29 C33 62.10(19) . . . . ?
C14 C13 C12 C11 -2.5(3) . . . . ?
C7 C2 C1 F3B 164.3(5) . . . . ?
C7 C2 C1 F2A -71.2(15) . . . . ?
C7 C2 C1 F1A 50.5(7) . . . . ?
C7 C2 C1 F2B -93.1(4) . . . . ?
C7 C2 C1 F3A 151.9(7) . . . . ?
C7 C2 C1 F1B 22.1(14) . . . . ?
C21 C16 C13 C12 174.88(17) . . . . ?
C21 C16 C13 C14 -5.1(3) . . . . ?
C21 C16 C17 C18 -1.3(3) . . . . ?
C31 C25 C26 C27 -58.25(19) . . . . ?
C31 C32 C33 C29 -59.6(2) . . . . ?
C31 C32 C34 C27 60.4(2) . . . . ?
C20 C19 C18 C17 -0.1(3) . . . . ?
C20 C19 C18 C23 179.46(17) . . . . ?
C15 C10 C11 C8 -179.80(17) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C15 C10 C9 O2 -3.0(3) . . . . ?
C15 C10 C9 N1 179.74(19) . . . . ?
C33 C32 C34 C27 -59.9(2) . . . . ?
C22 O3 C19 C18 -178.28(16) . . . . ?
C22 O3 C19 C20 2.0(3) . . . . ?
C34 C32 C33 C29 60.91(19) . . . . ?
C1 C2 C7 C6 -179.98(18) . . . . ?
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
9.0332 0.1154 -14.8723 0.5708 0.2306 0.7880
0.5905 -5.3968 20.8784 0.3885 0.1570 -0.9080
-0.9171 5.4768 -20.6813 -0.4146 -0.1675 0.8944
3.7594 -9.5243 -14.5686 -0.2495 0.6175 0.7459
-1.1507 -17.2950 14.2379 -0.3048 0.7545 -0.5812
-3.9296 7.3441 16.4916 0.2115 -0.5236 -0.8253
1.0241 17.5341 -13.7079 0.3117 -0.7715 0.5547
-8.1022 -1.9377 17.0683 -0.4796 -0.1375 -0.8666
