#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:46:08 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193497 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125590.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_4125590
loop_
_publ_author_name
'Lange, Ralph Z.'
'Hofer, Gregor'
'Weber, Thomas'
'Schlüter, A Dieter'
_publ_section_title
;
 A Two-Dimensional Polymer Synthesized through Topochemical [2 +
 2]-Cycloaddition on the Multigram Scale.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2053
_journal_page_last               2059
_journal_paper_doi               10.1021/jacs.6b11857
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C23 H27 O, B F4, H2 O'
_chemical_formula_sum            'C23 H29 B F4 O2'
_chemical_formula_weight         424.27
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-07-22
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   27.2965(7)
_cell_length_b                   27.2965(7)
_cell_length_c                   16.2071(6)
_cell_measurement_reflns_used    27483
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.02
_cell_measurement_theta_min      3
_cell_volume                     10458.0(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device_type  'BM01a at ESRF'
_diffrn_measurement_method       Transmission
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6935
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27483
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        24.589
_diffrn_reflns_theta_max         32.018
_diffrn_reflns_theta_min         2.081
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       Rhombohedra
_exptl_crystal_F_000             4032
_exptl_crystal_size_max          500
_exptl_crystal_size_mid          450
_exptl_crystal_size_min          400
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         7469
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      2.159
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.1724
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5211
_refine_ls_wR_factor_ref         0.5422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5236
_reflns_number_total             7469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11857_si_001.cif
_cod_data_source_block           mono_syn
_cod_depositor_comments          'Adding full bibliography for 4125590.cif.'
_cod_original_cell_volume        10458.0(7)
_cod_database_code               4125590
_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.
;
_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,H) groups
2. Restrained distances
 C23A-C22A
 2.5 with sigma of 0.02
 C23A-C24A
 2.5 with sigma of 0.02
 C24A-C22A
 2.5 with sigma of 0.02
 F3A-F2A
 2.35 with sigma of 0.02
 F2A-F4A
 2.35 with sigma of 0.02
 F4A-F3A
 2.35 with sigma of 0.02
 C21A-C23A \\sim C21A-C24A \\sim C21A-C22A \\sim C0AA-C1AA \\sim C0AA-C2AA
\\sim C0AA-C3AA
 with sigma of 0.02
 O1-C14 \\sim O1-C15
 with sigma of 0.02
 C12A-C14 \\sim C12A-C11A \\sim C1BA-C0AB \\sim C13A-C11A
 with sigma of 0.02
 C4AA-C6AA \\sim C4AA-C7AA \\sim C21A-C23A \\sim C4AA-C5AA \\sim C21A-C22A
\\sim C21A-C24A
 with sigma of 0.02
 C0AA-C2AA \\sim C17A-C20A \\sim C0AA-C3AA \\sim C17A-C19A \\sim C17A-C18A
 with sigma of 0.02
 C17A-C15 \\sim C4AA-C14
 with sigma of 0.02
 F3A-B1 \\sim F4A-B1 \\sim F2A-B1 \\sim F1A-B1
 with sigma of 0.02
 C13A-C11A \\sim C13A-C15 \\sim C1BA-C0AB \\sim C12A-C11A \\sim C1BA-C14 \\sim
C12A-C14
 with sigma of 0.02
 F3B-B1B \\sim F3A-B1 \\sim F4B-B1B \\sim F1B-B1B \\sim F2A-B1 \\sim F1A-B1
\\sim F4A-B1 \\sim F2B-B1B
 with sigma of 0.02
 O1-C15 \\sim O1-C14
 with sigma of 0.02
 C13A-C15 \\sim C12A-C14 \\sim C1BA-C0AB \\sim C12A-C11A \\sim C13A-C11A \\sim
C6-C4 \\sim C6-C8 \\sim C8-
 C7 \\sim C5-C7 \\sim C5-C3 \\sim C3-C4 \\sim C1-C2
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(C1BA) = Uiso(C0AB) = Uiso(C21A) = Uiso(C17A)
Uiso(C4AA) = Uiso(C12A) = Uiso(C11A) = Uiso(C13A) = Uiso(C0AA)
Uiso(C24A) = Uiso(C23A) = Uiso(C22A)
Uiso(C6AA) = Uiso(C5AA) = Uiso(C7AA)
Uiso(C1AA) = Uiso(C3AA) = Uiso(C2AA)
Uiso(C19A) = Uiso(C20A) = Uiso(C18A)
4. Rigid body (RIGU) restrains
 F1A, B1, F4A, F3A, F2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H13B)=Sof(C7A)=Sof(H7A)=Sof(C4AB)=Sof(H4AB)=Sof(C0AB)=Sof(C1BA)=Sof(H1BA)=
 Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C24A)=Sof(H24A)=
 Sof(H24B)=Sof(H24C)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C17A)=
 Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19A)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=1-FVAR(1)
 Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(C10A)=Sof(H10A)=Sof(C0AA)=
 Sof(C4AA)=Sof(C9A)=Sof(H9A)=Sof(C5AA)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C3AA)=
 Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C6AA)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=
 Sof(C7AA)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=Sof(C1AA)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(1)
 Sof(F4B)=Sof(F1B)=Sof(B1B)=Sof(F2B)=Sof(F3B)=1-FVAR(2)
 Sof(F1A)=Sof(B1)=Sof(F4A)=Sof(F3A)=Sof(F2A)=FVAR(2)
6.a Free rotating group:
 O2(H2A,H2B)
6.b Ternary CH refined with riding coordinates:
 C7A(H7A), C4AB(H4AB)
6.c Aromatic/amide H refined with riding coordinates:
 C13A(H13A), C13A(H13B), C1(H1), C5(H5), C12A(H12A), C7(H7), C4(H4),
 C10A(H10A), C6(H6), C9A(H9A), C1BA(H1BA)
6.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C3AA(H3AA,H3AB,H3AC), C6AA(H6AA,H6AB,H6AC), C7AA(H7AA,
 H7AB,H7AC), C2AA(H2AA,H2AB,H2AC), C1AA(H1AA,H1AB,H1AC), C22A(H22A,H22B,H22C),
 C24A(H24A,H24B,H24C), C23A(H23A,H23B,H23C), C18A(H18A,H18B,H18C), C19A(H19A,
 H19B,H19C), C20A(H20A,H20B,H20C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.30753(9) 0.46813(10) 0.39305(14) 0.0559(6) Uani 1 1 d D . . . .
F1A F 0.5407(5) 0.5684(4) 0.3231(8) 0.079(2) Uani 0.396(15) 1 d D U P A 1
O2 O 0.7040(2) 0.62200(18) 0.7324(3) 0.1051(13) Uani 1 1 d . . . . .
H2A H 0.7348 0.6533 0.7381 0.158 Uiso 1 1 d G . . . .
H2B H 0.6761 0.6276 0.7357 0.158 Uiso 1 1 d G . . . .
C3 C 0.59472(12) 0.38334(11) 0.4428(2) 0.0606(8) Uani 1 1 d D . . . .
C14 C 0.29337(14) 0.42339(14) 0.4404(2) 0.0601(8) Uani 1 1 d D . . . .
C13A C 0.40226(13) 0.48946(13) 0.38448(18) 0.0563(5) Uiso 1 1 d D . . . .
H13A H 0.4394 0.5135 0.3680 0.068 Uiso 0.747(6) 1 calc R . P B 1
H13B H 0.4370 0.5091 0.3579 0.068 Uiso 0.253(6) 1 calc R . P B 2
C1 C 0.69043(11) 0.39177(11) 0.4430(2) 0.0595(8) Uani 1 1 d D . . . .
H1 H 0.7064 0.4309 0.4424 0.071 Uiso 1 1 calc R . . . .
C5 C 0.61202(13) 0.43561(12) 0.4060(2) 0.0608(8) Uani 1 1 d D . . . .
H5 H 0.6477 0.4554 0.3820 0.073 Uiso 1 1 calc R . . . .
C12A C 0.33303(17) 0.4077(2) 0.4590(3) 0.0563(5) Uiso 0.747(6) 1 d D . P B 1
H12A H 0.3229 0.3752 0.4898 0.068 Uiso 0.747(6) 1 calc R . P B 1
C2 C 0.63176(10) 0.35774(12) 0.4434(2) 0.0587(8) Uani 1 1 d D . . . .
C7 C 0.57649(12) 0.45858(13) 0.4049(2) 0.0614(8) Uani 1 1 d D . . . .
H7 H 0.5890 0.4940 0.3815 0.074 Uiso 1 1 calc R . . . .
C8 C 0.52240(13) 0.42884(14) 0.4385(2) 0.0649(9) Uani 1 1 d D . . . .
C11A C 0.38827(19) 0.44116(17) 0.4310(3) 0.0563(5) Uiso 0.747(6) 1 d D . P B 1
C4 C 0.54189(13) 0.35555(16) 0.4805(3) 0.0700(9) Uani 1 1 d D . . . .
H4 H 0.5307 0.3217 0.5082 0.084 Uiso 1 1 calc R . . . .
C10A C 0.42724(16) 0.42155(16) 0.4521(2) 0.0485(8) Uiso 0.747(6) 1 d . . P B 1
H10A H 0.4142 0.3889 0.4836 0.058 Uiso 0.747(6) 1 calc R . P B 1
C6 C 0.50550(15) 0.37734(15) 0.4775(3) 0.0706(9) Uani 1 1 d D . . . .
H6 H 0.4699 0.3575 0.5017 0.085 Uiso 1 1 calc R . . . .
C0AA C 0.36591(19) 0.5482(2) 0.3071(3) 0.0563(5) Uiso 0.747(6) 1 d D . P B 1
C4AA C 0.23149(19) 0.39360(18) 0.4660(3) 0.0563(5) Uiso 0.747(6) 1 d D . P B 1
C9A C 0.48210(16) 0.44925(16) 0.4275(2) 0.0469(8) Uiso 0.747(6) 1 d . . P B 1
H9A H 0.4953 0.4840 0.4015 0.056 Uiso 0.747(6) 1 calc R . P B 1
C5AA C 0.2299(3) 0.4208(2) 0.5490(3) 0.0699(8) Uiso 0.747(6) 1 d D . P B 1
H5AA H 0.2563 0.4194 0.5867 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H5AB H 0.1925 0.4004 0.5718 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H5AC H 0.2400 0.4595 0.5399 0.105 Uiso 0.747(6) 1 calc GR . P B 1
C3AA C 0.4285(3) 0.5942(3) 0.2976(4) 0.0879(11) Uiso 0.747(6) 1 d D . P B 1
H3AA H 0.4438 0.6101 0.3507 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H3AB H 0.4314 0.6234 0.2615 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H3AC H 0.4494 0.5777 0.2747 0.132 Uiso 0.747(6) 1 calc GR . P B 1
C6AA C 0.2092(2) 0.3304(2) 0.4795(3) 0.0699(8) Uiso 0.747(6) 1 d D . P B 1
H6AA H 0.2192 0.3153 0.4332 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H6AB H 0.1688 0.3111 0.4851 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H6AC H 0.2256 0.3253 0.5288 0.105 Uiso 0.747(6) 1 calc GR . P B 1
B1 B 0.5954(6) 0.6093(5) 0.3087(8) 0.072(4) Uani 0.396(15) 1 d D U P A 1
C7AA C 0.1951(2) 0.4027(2) 0.4034(3) 0.0699(8) Uiso 0.747(6) 1 d D . P B 1
H7AA H 0.2074 0.4423 0.4000 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H7AB H 0.1563 0.3822 0.4205 0.105 Uiso 0.747(6) 1 calc GR . P B 1
H7AC H 0.1989 0.3893 0.3503 0.105 Uiso 0.747(6) 1 calc GR . P B 1
C2AA C 0.3328(3) 0.5746(3) 0.3420(4) 0.0879(11) Uiso 0.747(6) 1 d D . P B 1
H2AA H 0.2931 0.5473 0.3409 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H2AB H 0.3399 0.6069 0.3093 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H2AC H 0.3444 0.5864 0.3979 0.132 Uiso 0.747(6) 1 calc GR . P B 1
C1AA C 0.3433(3) 0.5201(3) 0.2235(4) 0.0879(11) Uiso 0.747(6) 1 d D . P B 1
H1AA H 0.3652 0.5037 0.2043 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H1AB H 0.3462 0.5480 0.1846 0.132 Uiso 0.747(6) 1 calc GR . P B 1
H1AC H 0.3045 0.4911 0.2291 0.132 Uiso 0.747(6) 1 calc GR . P B 1
C7A C 0.5125(8) 0.4844(8) 0.4464(11) 0.076(4) Uiso 0.253(6) 1 d . . P B 2
H7A H 0.5077 0.4961 0.3913 0.091 Uiso 0.253(6) 1 calc R . P B 2
C4AB C 0.4567(8) 0.4629(8) 0.4970(10) 0.077(4) Uiso 0.253(6) 1 d . . P B 2
H4AB H 0.4497 0.4294 0.5285 0.092 Uiso 0.253(6) 1 calc R . P B 2
C0AB C 0.3945(7) 0.4482(8) 0.4463(12) 0.077(3) Uiso 0.253(6) 1 d D . P B 2
C1BA C 0.3380(6) 0.4164(9) 0.4696(13) 0.077(3) Uiso 0.253(6) 1 d D . P B 2
H1BA H 0.3289 0.3878 0.5081 0.092 Uiso 0.253(6) 1 calc R . P B 2
C15 C 0.35983(13) 0.50107(15) 0.3631(2) 0.0600(8) Uani 1 1 d D . . . .
C21A C 0.2428(7) 0.3863(7) 0.4904(9) 0.077(3) Uiso 0.253(6) 1 d D . P B 2
C22A C 0.2236(13) 0.4270(10) 0.5196(16) 0.107(4) Uiso 0.253(6) 1 d D . P B 2
H22A H 0.2379 0.4401 0.5741 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H22B H 0.1830 0.4079 0.5204 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H22C H 0.2378 0.4587 0.4827 0.161 Uiso 0.253(6) 1 calc GR . P B 2
C24A C 0.2422(12) 0.3491(10) 0.5621(13) 0.107(4) Uiso 0.253(6) 1 d D . P B 2
H24A H 0.2700 0.3380 0.5521 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H24B H 0.2055 0.3161 0.5662 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H24C H 0.2510 0.3702 0.6127 0.161 Uiso 0.253(6) 1 calc GR . P B 2
C23A C 0.2068(11) 0.3486(10) 0.4203(12) 0.107(4) Uiso 0.253(6) 1 d D . P B 2
H23A H 0.1840 0.3632 0.3981 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H23B H 0.1828 0.3110 0.4407 0.161 Uiso 0.253(6) 1 calc GR . P B 2
H23C H 0.2310 0.3479 0.3779 0.161 Uiso 0.253(6) 1 calc GR . P B 2
C17A C 0.3526(7) 0.5334(7) 0.2915(9) 0.077(3) Uiso 0.253(6) 1 d D . P B 2
C18A C 0.3046(9) 0.5460(11) 0.3015(16) 0.098(4) Uiso 0.253(6) 1 d D . P B 2
H18A H 0.2694 0.5131 0.2869 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H18B H 0.3111 0.5769 0.2661 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H18C H 0.3030 0.5561 0.3578 0.147 Uiso 0.253(6) 1 calc GR . P B 2
C19A C 0.3773(11) 0.5283(11) 0.2101(12) 0.098(4) Uiso 0.253(6) 1 d D . P B 2
H19A H 0.4137 0.5320 0.2197 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H19B H 0.3812 0.5575 0.1732 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H19C H 0.3525 0.4920 0.1860 0.147 Uiso 0.253(6) 1 calc GR . P B 2
C20A C 0.3953(10) 0.5941(8) 0.3212(15) 0.098(4) Uiso 0.253(6) 1 d D . P B 2
H20A H 0.3844 0.6002 0.3748 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H20B H 0.3955 0.6211 0.2830 0.147 Uiso 0.253(6) 1 calc GR . P B 2
H20C H 0.4325 0.5986 0.3240 0.147 Uiso 0.253(6) 1 calc GR . P B 2
F4A F 0.6012(4) 0.6591(4) 0.3404(9) 0.106(4) Uani 0.396(15) 1 d D U P A 1
F3A F 0.6107(4) 0.6149(7) 0.2270(5) 0.112(5) Uani 0.396(15) 1 d D U P A 1
F2A F 0.6313(4) 0.5952(4) 0.3490(5) 0.096(3) Uani 0.396(15) 1 d D U P A 1
F4B F 0.5975(7) 0.6449(4) 0.2366(6) 0.168(5) Uani 0.604(15) 1 d D . P A 2
F1B F 0.5317(6) 0.5769(7) 0.3145(16) 0.190(8) Uani 0.604(15) 1 d D . P A 2
B1B B 0.5866(5) 0.6111(4) 0.3016(6) 0.079(3) Uani 0.604(15) 1 d D . P A 2
F2B F 0.6116(8) 0.6472(6) 0.3667(5) 0.225(10) Uani 0.604(15) 1 d D . P A 2
F3B F 0.6142(5) 0.5824(5) 0.2849(19) 0.239(12) Uani 0.604(15) 1 d 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 0.0030 0.0020 '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'
B B 0.0013 0.0007 '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'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C14 O1 C15 123.3(2) . .
H2A O2 H2B 109.6 . .
C5 C3 C2 121.4(3) . .
C4 C3 C5 118.3(3) . .
C4 C3 C2 120.2(3) . .
O1 C14 C12A 120.0(3) . .
O1 C14 C4AA 112.6(3) . .
O1 C14 C1BA 116.5(9) . .
O1 C14 C21A 133.6(7) . .
C12A C14 C4AA 127.4(4) . .
C1BA C14 C21A 107.4(11) . .
C11A C13A H13A 120.5 . .
C0AB C13A H13B 118.7 . .
C15 C13A H13A 120.5 . .
C15 C13A H13B 118.7 . .
C15 C13A C11A 119.0(3) . .
C15 C13A C0AB 122.5(8) . .
C2 C1 H1 119.3 3_665 .
C2 C1 H1 119.3 . .
C2 C1 C2 121.4(3) . 3_665
C3 C5 H5 119.6 . .
C3 C5 C7 120.7(3) . .
C7 C5 H5 119.6 . .
C14 C12A H12A 120.5 . .
C14 C12A C11A 119.0(4) . .
C11A C12A H12A 120.5 . .
C1 C2 C3 120.7(2) 2_655 .
C1 C2 C3 120.7(2) . .
C1 C2 C1 118.6(3) . 2_655
C5 C7 H7 119.8 . .
C8 C7 C5 120.4(3) . .
C8 C7 H7 119.8 . .
C7 C8 C6 119.1(3) . .
C7 C8 C9A 120.5(3) . .
C7 C8 C7A 96.1(6) . .
C6 C8 C9A 120.3(3) . .
C6 C8 C7A 139.2(7) . .
C13A C11A C10A 124.8(4) . .
C12A C11A C13A 119.4(4) . .
C12A C11A C10A 115.8(3) . .
C3 C4 H4 119.4 . .
C6 C4 C3 121.3(3) . .
C6 C4 H4 119.4 . .
C11A C10A H10A 118.9 . .
C9A C10A C11A 122.2(3) . .
C9A C10A H10A 118.9 . .
C8 C6 H6 120.0 . .
C4 C6 C8 120.0(3) . .
C4 C6 H6 120.0 . .
C2AA C0AA C3AA 109.4(5) . .
C2AA C0AA C1AA 112.5(5) . .
C1AA C0AA C3AA 109.0(5) . .
C15 C0AA C3AA 110.9(4) . .
C15 C0AA C2AA 109.9(4) . .
C15 C0AA C1AA 105.1(4) . .
C14 C4AA C5AA 105.7(4) . .
C14 C4AA C6AA 110.6(4) . .
C14 C4AA C7AA 111.7(4) . .
C6AA C4AA C5AA 109.0(4) . .
C7AA C4AA C5AA 108.9(4) . .
C7AA C4AA C6AA 110.7(4) . .
C8 C9A H9A 117.3 . .
C10A C9A C8 125.4(3) . .
C10A C9A H9A 117.3 . .
C4AA C5AA H5AA 109.5 . .
C4AA C5AA H5AB 109.5 . .
C4AA C5AA H5AC 109.5 . .
H5AA C5AA H5AB 109.5 . .
H5AA C5AA H5AC 109.5 . .
H5AB C5AA H5AC 109.5 . .
C0AA C3AA H3AA 109.5 . .
C0AA C3AA H3AB 109.5 . .
C0AA C3AA H3AC 109.5 . .
H3AA C3AA H3AB 109.5 . .
H3AA C3AA H3AC 109.5 . .
H3AB C3AA H3AC 109.5 . .
C4AA C6AA H6AA 109.5 . .
C4AA C6AA H6AB 109.5 . .
C4AA C6AA H6AC 109.5 . .
H6AA C6AA H6AB 109.5 . .
H6AA C6AA H6AC 109.5 . .
H6AB C6AA H6AC 109.5 . .
F1A B1 F4A 106.3(11) . .
F1A B1 F3A 113.8(12) . .
F1A B1 F2A 109.2(11) . .
F3A B1 F4A 111.6(12) . .
F3A B1 F2A 105.5(10) . .
F2A B1 F4A 110.5(10) . .
C4AA C7AA H7AA 109.5 . .
C4AA C7AA H7AB 109.5 . .
C4AA C7AA H7AC 109.5 . .
H7AA C7AA H7AB 109.5 . .
H7AA C7AA H7AC 109.5 . .
H7AB C7AA H7AC 109.5 . .
C0AA C2AA H2AA 109.5 . .
C0AA C2AA H2AB 109.5 . .
C0AA C2AA H2AC 109.5 . .
H2AA C2AA H2AB 109.5 . .
H2AA C2AA H2AC 109.5 . .
H2AB C2AA H2AC 109.5 . .
C0AA C1AA H1AA 109.5 . .
C0AA C1AA H1AB 109.5 . .
C0AA C1AA H1AC 109.5 . .
H1AA C1AA H1AB 109.5 . .
H1AA C1AA H1AC 109.5 . .
H1AB C1AA H1AC 109.5 . .
C8 C7A H7A 109.6 . .
C4AB C7A C8 105.6(13) . .
C4AB C7A C8 128.8(14) 10_666 .
C4AB C7A H7A 109.6 10_666 .
C4AB C7A H7A 109.6 . .
C4AB C7A C4AB 90.7(13) 10_666 .
C7A C4AB C7A 89.3(13) 10_666 .
C7A C4AB H4AB 108.6 . .
C7A C4AB H4AB 108.6 10_666 .
C7A C4AB C0AB 120.5(15) 10_666 .
C7A C4AB C0AB 119.6(13) . .
C0AB C4AB H4AB 108.6 . .
C13A C0AB C4AB 113.7(12) . .
C1BA C0AB C13A 111.2(17) . .
C1BA C0AB C4AB 131.5(15) . .
C14 C1BA H1BA 117.0 . .
C0AB C1BA C14 126.0(18) . .
C0AB C1BA H1BA 117.0 . .
O1 C15 C13A 119.1(3) . .
O1 C15 C0AA 114.5(3) . .
O1 C15 C17A 105.1(6) . .
C13A C15 C0AA 126.4(3) . .
C13A C15 C17A 133.2(7) . .
C14 C21A C22A 102.4(15) . .
C14 C21A C24A 124.2(16) . .
C14 C21A C23A 96.9(14) . .
C22A C21A C24A 110.7(13) . .
C23A C21A C22A 112.8(13) . .
C23A C21A C24A 109.2(12) . .
C21A C22A H22A 109.5 . .
C21A C22A H22B 109.5 . .
C21A C22A H22C 109.5 . .
H22A C22A H22B 109.5 . .
H22A C22A H22C 109.5 . .
H22B C22A H22C 109.5 . .
C21A C24A H24A 109.5 . .
C21A C24A H24B 109.5 . .
C21A C24A H24C 109.5 . .
H24A C24A H24B 109.5 . .
H24A C24A H24C 109.5 . .
H24B C24A H24C 109.5 . .
C21A C23A H23A 109.5 . .
C21A C23A H23B 109.5 . .
C21A C23A H23C 109.5 . .
H23A C23A H23B 109.5 . .
H23A C23A H23C 109.5 . .
H23B C23A H23C 109.5 . .
C15 C17A C20A 97.8(13) . .
C18A C17A C15 115.1(13) . .
C18A C17A C19A 125.9(17) . .
C18A C17A C20A 89.9(17) . .
C19A C17A C15 114.4(14) . .
C19A C17A C20A 103.7(17) . .
C17A C18A H18A 109.5 . .
C17A C18A H18B 109.5 . .
C17A C18A H18C 109.5 . .
H18A C18A H18B 109.5 . .
H18A C18A H18C 109.5 . .
H18B C18A H18C 109.5 . .
C17A C19A H19A 109.5 . .
C17A C19A H19B 109.5 . .
C17A C19A H19C 109.5 . .
H19A C19A H19B 109.5 . .
H19A C19A H19C 109.5 . .
H19B C19A H19C 109.5 . .
C17A C20A H20A 109.5 . .
C17A C20A H20B 109.5 . .
C17A C20A H20C 109.5 . .
H20A C20A H20B 109.5 . .
H20A C20A H20C 109.5 . .
H20B C20A H20C 109.5 . .
F4B B1B F2B 104.6(10) . .
F4B B1B F3B 104.3(14) . .
F1B B1B F4B 113.1(15) . .
F1B B1B F2B 111.4(14) . .
F1B B1B F3B 112.5(12) . .
F3B B1B F2B 110.5(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.326(4) .
O1 C15 1.341(4) .
F1A B1 1.365(11) .
O2 H2A 0.8533 .
O2 H2B 0.8496 .
C3 C5 1.393(3) .
C3 C2 1.489(4) .
C3 C4 1.391(3) .
C14 C12A 1.382(3) .
C14 C4AA 1.521(5) .
C14 C1BA 1.406(13) .
C14 C21A 1.480(17) .
C13A H13A 0.9300 .
C13A H13B 0.9300 .
C13A C11A 1.396(3) .
C13A C0AB 1.44(2) .
C13A C15 1.389(3) .
C1 H1 0.9300 .
C1 C2 1.393(3) .
C1 C2 1.406(4) 3_665
C5 H5 0.9300 .
C5 C7 1.394(3) .
C12A H12A 0.9300 .
C12A C11A 1.392(3) .
C2 C1 1.406(4) 2_655
C7 H7 0.9300 .
C7 C8 1.392(3) .
C8 C6 1.393(3) .
C8 C9A 1.471(5) .
C8 C7A 1.673(19) .
C11A C10A 1.451(6) .
C4 H4 0.9300 .
C4 C6 1.391(3) .
C10A H10A 0.9300 .
C10A C9A 1.357(5) .
C6 H6 0.9300 .
C0AA C3AA 1.541(8) .
C0AA C2AA 1.521(8) .
C0AA C1AA 1.526(7) .
C0AA C15 1.515(5) .
C4AA C5AA 1.547(6) .
C4AA C6AA 1.530(7) .
C4AA C7AA 1.524(6) .
C9A H9A 0.9300 .
C5AA H5AA 0.9600 .
C5AA H5AB 0.9600 .
C5AA H5AC 0.9600 .
C3AA H3AA 0.9600 .
C3AA H3AB 0.9600 .
C3AA H3AC 0.9600 .
C6AA H6AA 0.9600 .
C6AA H6AB 0.9600 .
C6AA H6AC 0.9600 .
B1 F4A 1.386(11) .
B1 F3A 1.373(12) .
B1 F2A 1.384(12) .
C7AA H7AA 0.9600 .
C7AA H7AB 0.9600 .
C7AA H7AC 0.9600 .
C2AA H2AA 0.9600 .
C2AA H2AB 0.9600 .
C2AA H2AC 0.9600 .
C1AA H1AA 0.9600 .
C1AA H1AB 0.9600 .
C1AA H1AC 0.9600 .
C7A H7A 0.9800 .
C7A C4AB 1.56(3) .
C7A C4AB 1.55(3) 10_666
C4AB C7A 1.55(3) 10_666
C4AB H4AB 0.9800 .
C4AB C0AB 1.74(3) .
C0AB C1BA 1.392(4) .
C1BA H1BA 0.9300 .
C15 C17A 1.530(14) .
C21A C22A 1.520(13) .
C21A C24A 1.539(13) .
C21A C23A 1.516(13) .
C22A H22A 0.9600 .
C22A H22B 0.9600 .
C22A H22C 0.9600 .
C24A H24A 0.9600 .
C24A H24B 0.9600 .
C24A H24C 0.9600 .
C23A H23A 0.9600 .
C23A H23B 0.9600 .
C23A H23C 0.9600 .
C17A C18A 1.520(14) .
C17A C19A 1.521(14) .
C17A C20A 1.551(14) .
C18A H18A 0.9600 .
C18A H18B 0.9600 .
C18A H18C 0.9600 .
C19A H19A 0.9600 .
C19A H19B 0.9600 .
C19A H19C 0.9600 .
C20A H20A 0.9600 .
C20A H20B 0.9600 .
C20A H20C 0.9600 .
F4B B1B 1.333(10) .
F1B B1B 1.329(11) .
B1B F2B 1.370(11) .
B1B F3B 1.356(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_4
O1 C14 C12A C11A 3.3(6) . .
O1 C14 C4AA C5AA -91.4(4) . .
O1 C14 C4AA C6AA 150.8(3) . .
O1 C14 C4AA C7AA 26.9(5) . .
O1 C14 C1BA C0AB -8(2) . .
O1 C14 C21A C22A -33.1(15) . .
O1 C14 C21A C24A -159.1(12) . .
O1 C14 C21A C23A 82.1(12) . .
O1 C15 C17A C18A 31.4(16) . .
O1 C15 C17A C19A -126.0(14) . .
O1 C15 C17A C20A 125.0(12) . .
C3 C5 C7 C8 -1.8(5) . .
C3 C4 C6 C8 -2.0(6) . .
C14 O1 C15 C13A -2.3(5) . .
C14 O1 C15 C0AA 177.2(3) . .
C14 O1 C15 C17A 161.6(6) . .
C14 C12A C11A C13A -0.4(6) . .
C14 C12A C11A C10A -179.2(4) . .
C13A C11A C10A C9A -0.2(6) . .
C13A C0AB C1BA C14 -2(3) . .
C13A C15 C17A C18A -168.0(12) . .
C13A C15 C17A C19A 34.6(19) . .
C13A C15 C17A C20A -74.4(14) . .
C5 C3 C2 C1 29.3(5) . .
C5 C3 C2 C1 -149.6(4) . 2_655
C5 C3 C4 C6 3.9(6) . .
C5 C7 C8 C6 3.7(5) . .
C5 C7 C8 C9A -171.7(3) . .
C5 C7 C8 C7A 162.3(7) . .
C12A C14 C4AA C5AA 90.6(5) . .
C12A C14 C4AA C6AA -27.2(6) . .
C12A C14 C4AA C7AA -151.0(4) . .
C12A C11A C10A C9A 178.6(4) . .
C2 C3 C5 C7 179.0(3) . .
C2 C3 C4 C6 -177.1(4) . .
C2 C1 C2 C3 -179.9(2) 3_665 .
C2 C1 C2 C1 -1.0(8) 3_665 2_655
C7 C8 C6 C4 -1.8(6) . .
C7 C8 C9A C10A 174.8(3) . .
C7 C8 C7A C4AB -171.1(10) . .
C7 C8 C7A C4AB -67.1(16) . 10_666
C8 C7A C4AB C7A 130.9(15) . 10_666
C8 C7A C4AB C0AB -104.0(16) . .
C11A C13A C15 O1 5.1(5) . .
C11A C13A C15 C0AA -174.3(4) . .
C11A C10A C9A C8 -172.9(4) . .
C4 C3 C5 C7 -2.0(5) . .
C4 C3 C2 C1 31.4(5) . 2_655
C4 C3 C2 C1 -149.8(4) . .
C6 C8 C9A C10A -0.5(5) . .
C6 C8 C7A C4AB -20.3(17) . .
C6 C8 C7A C4AB 83.7(18) . 10_666
C4AA C14 C12A C11A -178.8(4) . .
C9A C8 C6 C4 173.6(4) . .
C3AA C0AA C15 O1 162.2(4) . .
C3AA C0AA C15 C13A -18.4(6) . .
C2AA C0AA C15 O1 41.1(5) . .
C2AA C0AA C15 C13A -139.4(4) . .
C1AA C0AA C15 O1 -80.1(5) . .
C1AA C0AA C15 C13A 99.3(5) . .
C7A C8 C6 C4 -148.1(10) . .
C7A C4AB C0AB C13A 66(2) 10_666 .
C7A C4AB C0AB C13A -42(2) . .
C7A C4AB C0AB C1BA -90(3) 10_666 .
C7A C4AB C0AB C1BA 161(2) . .
C4AB C7A C4AB C7A -0.004(3) 10_666 10_666
C4AB C7A C4AB C0AB 125.2(19) 10_666 .
C4AB C0AB C1BA C14 154.8(18) . .
C0AB C13A C15 O1 -8.6(10) . .
C0AB C13A C15 C17A -167.1(12) . .
C1BA C14 C21A C22A 127.5(14) . .
C1BA C14 C21A C24A 1.6(17) . .
C1BA C14 C21A C23A -117.3(14) . .
C15 O1 C14 C12A -2.0(5) . .
C15 O1 C14 C4AA 179.9(3) . .
C15 O1 C14 C1BA 9.9(10) . .
C15 O1 C14 C21A 169.1(9) . .
C15 C13A C11A C12A -3.8(6) . .
C15 C13A C11A C10A 174.9(4) . .
C15 C13A C0AB C4AB -151.1(10) . .
C15 C13A C0AB C1BA 10.1(19) . .
C21A C14 C1BA C0AB -172.0(18) . .
