#------------------------------------------------------------------------------
#$Date: 2020-04-03 00:28:22 +0300 (Fri, 03 Apr 2020) $
#$Revision: 249965 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517537.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_4517537
loop_
_publ_author_name
'Docherty, Jamie H.'
'Nicholson, Kieran'
'Dominey, Andrew P.'
'Thomas, Stephen P.'
_publ_section_title
;
 A Boron--Boron Double Transborylation Strategy for the Synthesis of
 gem-Diborylalkanes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              4686
_journal_paper_doi               10.1021/acscatal.0c00869
_journal_year                    2020
_chemical_formula_moiety         'C22 H34 B2 O2'
_chemical_formula_sum            'C22 H34 B2 O2'
_chemical_formula_weight         352.11
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0776(2)
_cell_length_b                   6.63350(10)
_cell_length_c                   21.5511(3)
_cell_measurement_reflns_used    12507
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9730
_cell_measurement_theta_min      4.5890
_cell_volume                     2103.57(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -82.00  15.00   1.00   10.00    --  -41.67 101.00 -84.00   97
  2  ω      7.00  83.00   1.00   10.00    --   41.67-101.00 171.00   76
  3  ω    104.00 178.00   1.00   30.00    --  111.00 101.00 -84.00   74
  4  ω     32.00 107.00   1.00   30.00    --  111.00-101.00 171.00   75
  5  ω   -114.00 -19.00   1.00   10.00    --  -41.67 -38.00 120.00   95
  6  ω   -114.00 -19.00   1.00   10.00    --  -41.67 -38.00-150.00   95
  7  ω   -114.00 -19.00   1.00   10.00    --  -41.67 -38.00 -60.00   95
  8  ω     15.00 112.00   1.00   10.00    --   41.67  57.00  60.00   97
  9  ω     37.00 142.00   1.00   30.00    --  111.00 -77.00-180.00  105
 10  ω     30.00 107.00   1.00   30.00    --  111.00 -94.00-120.00   77
 11  ω     36.00 135.00   1.00   30.00    --  111.00 -30.00 150.00   99
 12  ω     97.00 178.00   1.00   30.00    --  111.00 125.00-120.00   81
 13  ω     87.00 178.00   1.00   30.00    --  111.00  45.00 -30.00   91
 14  ω     97.00 178.00   1.00   30.00    --  111.00 125.00   0.00   81
 15  ω     30.00 107.00   1.00   30.00    --  111.00 -94.00   0.00   77
 16  ω     31.00 156.00   1.00   30.00    --  111.00 -15.00   0.00  125
 17  ω     30.00 107.00   1.00   30.00    --  111.00 -94.00 120.00   77
 18  ω     36.00 109.00   1.00   30.00    --  111.00-111.00 -58.63   73
 19  ω     87.00 178.00   1.00   30.00    --  111.00  30.00  30.00   91
 20  ω     66.00 178.00   1.00   30.00    --  111.00  15.00-120.00  112
 21  ω    103.00 178.00   1.00   30.00    --  111.00  77.00  60.00   75
 22  ω     30.00 107.00   1.00   30.00    --  111.00 -94.00-180.00   77
 23  ω     39.00 112.00   1.00   30.00    --  111.00-125.00-180.00   73
 24  ω     41.00 139.00   1.00   30.00    --  111.00 -61.00 -30.00   98
 25  ω     39.00 112.00   1.00   30.00    --  111.00-125.00-120.00   73
 26  ω     58.00 111.00   1.00   30.00    --  111.00-125.00   0.00   53
 27  ω     80.00 123.00   1.00   30.00    --  111.00-138.00 148.30   43
 28  ω     50.00 106.00   1.00   30.00    --  111.00 -94.00 -30.00   56
 29  ω     80.00 106.00   1.00   30.00    --  111.00-101.00 149.70   26
 30  ω     45.00  71.00   1.00   30.00    --  111.00 -94.00-150.00   26
 31  ω     41.00 129.00   1.00   30.00    --  111.00 -45.00 -60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0423284000
_diffrn_orient_matrix_UB_12      -0.1057117000
_diffrn_orient_matrix_UB_13      -0.0502392000
_diffrn_orient_matrix_UB_21      -0.0913571000
_diffrn_orient_matrix_UB_22      0.0158527000
_diffrn_orient_matrix_UB_23      -0.0485455000
_diffrn_orient_matrix_UB_31      0.0287543000
_diffrn_orient_matrix_UB_32      0.2061460000
_diffrn_orient_matrix_UB_33      -0.0220239000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33239
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.058
_diffrn_reflns_theta_min         4.204
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  0.95644
_exptl_absorpt_correction_T_min  0.95644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of pentane and hexane  by slow cooling to 233 K'
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     79
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0664
_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)+(0.1149P)²+0.8068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3775
_reflns_number_total             4385
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00869_si_001.cif
_cod_data_source_block           se19005b
_cod_database_code               4517537
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H32 B2 O2'
_chemical_oxdiff_usercomment     '@ 120 K JD1 1.071'
_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 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C20 \\sim C15-C20A
 with sigma of 0.02
 C22-C21 \\sim C22-C21A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C15-C21 \\sim C15-C21A
 with sigma of 0.04
 C22-C20 \\sim C22-C20A
 with sigma of 0.04
 C18-C17 \\sim C18-C17A
 with sigma of 0.02
 C17-C16 \\sim C17A-C16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17A) = Uanis(C17)
Uanis(C13A) = Uanis(C13)
4. Rigid body (RIGU) restrains
 O1A, O2A, C9, C10A, C11A, C12, C13A, C14A, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H15A)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21C)=Sof(H21D)=
 Sof(H22C)=Sof(H22D)=1-FVAR(1)
 Sof(H15)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H22A)=
 Sof(H22B)=FVAR(1)
 Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(H18C)=Sof(H18D)=1-FVAR(2)
 Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H18A)=Sof(H18B)=FVAR(2)
 Sof(O1A)=Sof(O2A)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=Sof(C11A)=Sof(H11D)=
 Sof(H11E)=Sof(H11F)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C14A)=
 Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(3)
 Sof(O1)=Sof(O2)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(H14C)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15), C15(H15A), C19(H19)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C16(H16C,H16D), C17(H17A,H17B), C17A(H17C,H17D),
 C18(H18A,H18B), C18(H18C,H18D), C20(H20A,H20B), C20A(H20C,H20D), C21(H21A,
 H21B), C21A(H21C,H21D), C22(H22A,H22B), C22(H22C,H22D)
6.c Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F), C11(H11A,H11B,H11C), C11A(H11D,
 H11E,H11F), C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C14(H14A,H14B,H14C),
 C14A(H14D,H14E,H14F)
6.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_olex2_date_sample_data_collection 2019-10-17
_olex2_date_sample_submission    2019-10-17
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id JD11.071
_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 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.489
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 0.22279(17) 0.3891(5) 0.47423(12) 0.0309(5) Uani 0.890(4) 1 d . . P A 1
O1A O 0.1931(14) 0.367(3) 0.4759(11) 0.027(4) Uani 0.110(4) 1 d . U P A 2
O2 O 0.2022(2) 0.0775(6) 0.42784(14) 0.0320(7) Uani 0.890(4) 1 d . . P A 1
O2A O 0.2294(18) 0.071(4) 0.4382(12) 0.029(4) Uani 0.110(4) 1 d . U P A 2
C1 C 0.20273(10) 0.3803(2) 0.35270(7) 0.0224(3) Uani 1 1 d . . . . .
H1 H 0.170721 0.283492 0.319744 0.027 Uiso 1 1 calc R . . . .
C2 C 0.14557(10) 0.5761(2) 0.34603(7) 0.0245(3) Uani 1 1 d . . . . .
H2A H 0.089488 0.550843 0.361627 0.029 Uiso 1 1 calc R . . . .
H2B H 0.180648 0.682034 0.373145 0.029 Uiso 1 1 calc R . . . .
C3 C 0.11987(9) 0.6517(2) 0.27833(7) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.06656(10) 0.5335(2) 0.23061(8) 0.0278(3) Uani 1 1 d . . . . .
H4 H 0.047873 0.402984 0.240668 0.033 Uiso 1 1 calc R . . . .
C5 C 0.04063(12) 0.6049(3) 0.16866(8) 0.0353(4) Uani 1 1 d . . . . .
H5 H 0.003539 0.524166 0.136829 0.042 Uiso 1 1 calc R . . . .
C6 C 0.06887(13) 0.7940(3) 0.15323(8) 0.0378(4) Uani 1 1 d . . . . .
H6 H 0.051765 0.842283 0.110796 0.045 Uiso 1 1 calc R . . . .
C7 C 0.12202(12) 0.9120(3) 0.19989(10) 0.0374(4) Uani 1 1 d . . . . .
H7 H 0.141515 1.041409 0.189490 0.045 Uiso 1 1 calc R . . . .
C8 C 0.14695(11) 0.8413(2) 0.26201(9) 0.0297(4) Uani 1 1 d . . . . .
H8 H 0.183042 0.923781 0.293799 0.036 Uiso 1 1 calc R . . . .
C9 C 0.20807(12) 0.2511(2) 0.52444(8) 0.0301(4) Uani 1 1 d . U . . .
C10 C 0.10826(15) 0.2806(4) 0.52800(11) 0.0428(6) Uani 0.890(4) 1 d . . P A 1
H10A H 0.093899 0.192120 0.560885 0.064 Uiso 0.890(4) 1 calc R . P A 1
H10B H 0.098367 0.421312 0.538586 0.064 Uiso 0.890(4) 1 calc R . P A 1
H10C H 0.068822 0.247156 0.486815 0.064 Uiso 0.890(4) 1 calc R . P A 1
C10A C 0.1610(17) 0.265(3) 0.5764(9) 0.054(5) Uani 0.110(4) 1 d . U P A 2
H10D H 0.183835 0.160692 0.608046 0.081 Uiso 0.110(4) 1 calc R . P A 2
H10E H 0.171748 0.398314 0.596377 0.081 Uiso 0.110(4) 1 calc R . P A 2
H10F H 0.095638 0.245973 0.559961 0.081 Uiso 0.110(4) 1 calc R . P A 2
C11 C 0.2687(2) 0.3099(4) 0.58657(11) 0.0515(7) Uani 0.890(4) 1 d . . P A 1
H11A H 0.258844 0.217801 0.619978 0.077 Uiso 0.890(4) 1 calc R . P A 1
H11B H 0.332338 0.302181 0.583011 0.077 Uiso 0.890(4) 1 calc R . P A 1
H11C H 0.254660 0.448036 0.597342 0.077 Uiso 0.890(4) 1 calc R . P A 1
C11A C 0.3250(17) 0.293(4) 0.5597(12) 0.065(7) Uani 0.110(4) 1 d . U P A 2
H11D H 0.342947 0.209484 0.597757 0.097 Uiso 0.110(4) 1 calc R . P A 2
H11E H 0.362152 0.258143 0.529148 0.097 Uiso 0.110(4) 1 calc R . P A 2
H11F H 0.334297 0.435794 0.571398 0.097 Uiso 0.110(4) 1 calc R . P A 2
C12 C 0.22453(13) 0.0401(3) 0.49703(8) 0.0338(4) Uani 1 1 d . U . . .
C13 C 0.1645(3) -0.1265(4) 0.51264(14) 0.0557(8) Uani 0.890(4) 1 d . . P A 1
H13A H 0.179299 -0.151532 0.558561 0.083 Uiso 0.890(4) 1 calc R . P A 1
H13B H 0.100675 -0.086300 0.499347 0.083 Uiso 0.890(4) 1 calc R . P A 1
H13C H 0.174781 -0.249790 0.490122 0.083 Uiso 0.890(4) 1 calc R . P A 1
C13A C 0.130(2) -0.080(3) 0.4910(12) 0.0557(8) Uani 0.110(4) 1 d . U P A 2
H13D H 0.120145 -0.110303 0.533594 0.083 Uiso 0.110(4) 1 calc R . P A 2
H13E H 0.079497 0.003704 0.468123 0.083 Uiso 0.110(4) 1 calc R . P A 2
H13F H 0.131808 -0.206028 0.467678 0.083 Uiso 0.110(4) 1 calc R . P A 2
C14 C 0.3249(2) -0.0167(7) 0.51369(14) 0.0707(11) Uani 0.890(4) 1 d . . P A 1
H14A H 0.343576 -0.043425 0.559414 0.106 Uiso 0.890(4) 1 calc R . P A 1
H14B H 0.334657 -0.137847 0.489990 0.106 Uiso 0.890(4) 1 calc R . P A 1
H14C H 0.361140 0.094567 0.502376 0.106 Uiso 0.890(4) 1 calc R . P A 1
C14A C 0.296(2) -0.116(4) 0.5304(12) 0.065(7) Uani 0.110(4) 1 d . U P A 2
H14D H 0.289549 -0.135096 0.574357 0.098 Uiso 0.110(4) 1 calc R . P A 2
H14E H 0.285236 -0.245025 0.507664 0.098 Uiso 0.110(4) 1 calc R . P A 2
H14F H 0.356838 -0.067353 0.530141 0.098 Uiso 0.110(4) 1 calc R . P A 2
C15 C 0.35762(11) 0.6006(2) 0.34325(10) 0.0362(4) Uani 1 1 d D . . . .
H15 H 0.323458 0.718231 0.355307 0.043 Uiso 0.621(11) 1 calc R . P B 1
H15A H 0.319599 0.715468 0.352589 0.043 Uiso 0.379(11) 1 calc R . P B 2
C16 C 0.36756(17) 0.6186(4) 0.27316(15) 0.0638(8) Uani 1 1 d D . . . .
H16A H 0.307069 0.647318 0.245860 0.077 Uiso 0.803(5) 1 calc R . P C 1
H16B H 0.407480 0.734751 0.269767 0.077 Uiso 0.803(5) 1 calc R . P C 1
H16C H 0.325706 0.727197 0.253469 0.077 Uiso 0.197(5) 1 calc R . P C 2
H16D H 0.429930 0.668266 0.274714 0.077 Uiso 0.197(5) 1 calc R . P C 2
C17 C 0.40714(17) 0.4279(4) 0.24745(13) 0.0459(7) Uani 0.803(5) 1 d D . P C 1
H17A H 0.398661 0.440679 0.200754 0.055 Uiso 0.803(5) 1 calc R . P C 1
H17B H 0.473317 0.422849 0.265676 0.055 Uiso 0.803(5) 1 calc R . P C 1
C17A C 0.3546(8) 0.4704(16) 0.2341(5) 0.0459(7) Uani 0.197(5) 1 d D . P C 2
H17C H 0.396789 0.487431 0.205120 0.055 Uiso 0.197(5) 1 calc R . P C 2
H17D H 0.292189 0.483066 0.207842 0.055 Uiso 0.197(5) 1 calc R . P C 2
C18 C 0.36646(16) 0.2369(4) 0.26166(11) 0.0512(5) Uani 1 1 d D . . . .
H18A H 0.402830 0.124292 0.250125 0.061 Uiso 0.803(5) 1 calc R . P C 1
H18B H 0.304552 0.226586 0.234503 0.061 Uiso 0.803(5) 1 calc R . P C 1
H18C H 0.319080 0.151959 0.234930 0.061 Uiso 0.197(5) 1 calc R . P C 2
H18D H 0.426214 0.185272 0.256892 0.061 Uiso 0.197(5) 1 calc R . P C 2
C19 C 0.36011(11) 0.2115(2) 0.33146(9) 0.0326(4) Uani 1 1 d . . . . .
H19 H 0.326020 0.085125 0.336203 0.039 Uiso 1 1 calc R . . . .
C20 C 0.4561(3) 0.5953(8) 0.3836(3) 0.0383(12) Uani 0.621(11) 1 d D . P B 1
H20A H 0.499400 0.612827 0.355534 0.046 Uiso 0.621(11) 1 calc R . P B 1
H20B H 0.464997 0.708161 0.414426 0.046 Uiso 0.621(11) 1 calc R . P B 1
C20A C 0.4394(7) 0.5672(18) 0.4033(5) 0.050(2) Uani 0.379(11) 1 d D . P B 2
H20C H 0.475689 0.692400 0.412081 0.060 Uiso 0.379(11) 1 calc R . P B 2
H20D H 0.414752 0.535602 0.441170 0.060 Uiso 0.379(11) 1 calc R . P B 2
C21 C 0.4755(3) 0.3952(5) 0.4197(3) 0.0430(12) Uani 0.621(11) 1 d D . P B 1
H21A H 0.439246 0.390005 0.452769 0.052 Uiso 0.621(11) 1 calc R . P B 1
H21B H 0.540510 0.391856 0.441473 0.052 Uiso 0.621(11) 1 calc R . P B 1
C21A C 0.5015(5) 0.3905(9) 0.3903(5) 0.048(2) Uani 0.379(11) 1 d D . P B 2
H21C H 0.528115 0.426287 0.353683 0.058 Uiso 0.379(11) 1 calc R . P B 2
H21D H 0.552041 0.373096 0.427870 0.058 Uiso 0.379(11) 1 calc R . P B 2
C22 C 0.45415(14) 0.2059(3) 0.37740(10) 0.0431(5) Uani 1 1 d D . . . .
H22A H 0.501442 0.190773 0.352279 0.052 Uiso 0.621(11) 1 calc R . P B 1
H22B H 0.457244 0.085846 0.405098 0.052 Uiso 0.621(11) 1 calc R . P B 1
H22C H 0.446241 0.148931 0.418315 0.052 Uiso 0.379(11) 1 calc R . P B 2
H22D H 0.493110 0.111245 0.359802 0.052 Uiso 0.379(11) 1 calc R . P B 2
B1 B 0.20941(11) 0.2789(3) 0.41941(8) 0.0227(3) Uani 1 1 d . U . . .
B2 B 0.30303(12) 0.4002(3) 0.34424(8) 0.0246(4) Uani 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'
B B 0.0090 0.0039 '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 0 2 0.0183
1 0 -2 0.0257
-1 0 -1 0.0197
1 0 1 0.0213
2 1 0 0.1400
-1 -1 1 0.1911
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
B1 O1 C9 106.6(2) . . ?
C9 O1A B1 114.7(16) . . ?
B1 O2 C12 107.1(3) . . ?
C12 O2A B1 112(2) . . ?
C2 C1 H1 107.5 . . ?
C2 C1 B1 111.56(12) . . ?
C2 C1 B2 116.74(12) . . ?
B1 C1 H1 107.5 . . ?
B2 C1 H1 107.5 . . ?
B2 C1 B1 105.77(12) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.85(12) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C4 C3 C2 120.60(14) . . ?
C8 C3 C2 121.11(14) . . ?
C8 C3 C4 118.29(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.75(16) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.07(17) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.76(16) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.07(16) . . ?
C8 C7 H7 120.0 . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 121.06(16) . . ?
C7 C8 H8 119.5 . . ?
O1 C9 C10 105.33(17) . . ?
O1 C9 C11 109.57(18) . . ?
O1 C9 C12 102.59(17) . . ?
O1A C9 C10A 124.2(13) . . ?
O1A C9 C11A 103.6(12) . . ?
O1A C9 C12 104.2(10) . . ?
C10 C9 C12 111.81(16) . . ?
C10A C9 C11A 105.4(14) . . ?
C10A C9 C12 119.6(9) . . ?
C11 C9 C10 109.62(18) . . ?
C11 C9 C12 117.06(18) . . ?
C12 C9 C11A 94.5(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10A H10D 109.5 . . ?
C9 C10A H10E 109.5 . . ?
C9 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11A H11D 109.5 . . ?
C9 C11A H11E 109.5 . . ?
C9 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
O2 C12 C9 102.20(19) . . ?
O2 C12 C13 109.4(2) . . ?
O2 C12 C14 106.0(2) . . ?
O2A C12 C9 105.8(13) . . ?
O2A C12 C13A 103.7(14) . . ?
O2A C12 C14A 112.2(17) . . ?
C9 C12 C13A 105.1(9) . . ?
C13 C12 C9 114.81(17) . . ?
C13 C12 C14 112.2(2) . . ?
C14 C12 C9 111.4(2) . . ?
C14A C12 C9 125.1(8) . . ?
C14A C12 C13A 102.6(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13A H13D 109.5 . . ?
C12 C13A H13E 109.5 . . ?
C12 C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C14A H14D 109.5 . . ?
C12 C14A H14E 109.5 . . ?
C12 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C16 C15 H15 110.9 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 C20A 125.3(5) . . ?
C16 C15 B2 103.94(17) . . ?
C20 C15 H15 110.9 . . ?
C20 C15 C16 105.3(3) . . ?
C20 C15 B2 114.5(2) . . ?
C20A C15 H15A 108.5 . . ?
B2 C15 H15 110.9 . . ?
B2 C15 H15A 108.5 . . ?
B2 C15 C20A 100.7(5) . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 H16C 106.6 . . ?
C15 C16 H16D 106.6 . . ?
H16A C16 H16B 107.6 . . ?
H16C C16 H16D 106.5 . . ?
C17 C16 C15 114.22(17) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C17A C16 C15 123.1(5) . . ?
C17A C16 H16C 106.6 . . ?
C17A C16 H16D 106.6 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C16 114.72(19) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17A H17C 107.4 . . ?
C16 C17A H17D 107.4 . . ?
C16 C17A C18 119.5(7) . . ?
H17C C17A H17D 107.0 . . ?
C18 C17A H17C 107.4 . . ?
C18 C17A H17D 107.4 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C17 C18 C19 114.63(19) . . ?
C17A C18 H18C 108.4 . . ?
C17A C18 H18D 108.4 . . ?
H18A C18 H18B 107.6 . . ?
H18C C18 H18D 107.5 . . ?
C19 C18 C17A 115.4(4) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C19 C18 H18C 108.4 . . ?
C19 C18 H18D 108.4 . . ?
C18 C19 H19 109.6 . . ?
C18 C19 C22 112.71(16) . . ?
C18 C19 B2 103.69(15) . . ?
C22 C19 H19 109.6 . . ?
C22 C19 B2 111.54(14) . . ?
B2 C19 H19 109.6 . . ?
C15 C20 H20A 109.4 . . ?
C15 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 C15 111.0(3) . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
C15 C20A H20C 109.6 . . ?
C15 C20A H20D 109.6 . . ?
H20C C20A H20D 108.1 . . ?
C21A C20A C15 110.2(7) . . ?
C21A C20A H20C 109.6 . . ?
C21A C20A H20D 109.6 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C20 C21 C22 114.4(4) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C20A C21A H21C 109.0 . . ?
C20A C21A H21D 109.0 . . ?
H21C C21A H21D 107.8 . . ?
C22 C21A C20A 112.9(9) . . ?
C22 C21A H21C 109.0 . . ?
C22 C21A H21D 109.0 . . ?
C19 C22 C21 113.81(19) . . ?
C19 C22 H22A 108.8 . . ?
C19 C22 H22B 108.8 . . ?
C19 C22 H22C 108.0 . . ?
C19 C22 H22D 108.0 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21A C22 C19 117.3(3) . . ?
C21A C22 H22C 108.0 . . ?
C21A C22 H22D 108.0 . . ?
H22A C22 H22B 107.7 . . ?
H22C C22 H22D 107.2 . . ?
O1 B1 C1 122.04(17) . . ?
O1A B1 O2A 102.6(15) . . ?
O1A B1 C1 128.2(9) . . ?
O2 B1 O1 114.3(2) . . ?
O2 B1 C1 123.62(19) . . ?
O2A B1 C1 129.1(12) . . ?
C1 B2 C19 122.02(13) . . ?
C15 B2 C1 126.61(14) . . ?
C15 B2 C19 111.28(14) . . ?
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 C9 1.470(3) . ?
O1 B1 1.366(3) . ?
O1A C9 1.28(2) . ?
O1A B1 1.42(2) . ?
O2 C12 1.476(3) . ?
O2 B1 1.356(4) . ?
O2A C12 1.30(3) . ?
O2A B1 1.45(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.5483(19) . ?
C1 B1 1.570(2) . ?
C1 B2 1.568(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(2) . ?
C3 C4 1.399(2) . ?
C3 C8 1.391(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.536(3) . ?
C9 C10A 1.455(19) . ?
C9 C11 1.499(3) . ?
C9 C11A 1.78(2) . ?
C9 C12 1.560(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12 C13 1.512(3) . ?
C12 C13A 1.62(3) . ?
C12 C14 1.525(3) . ?
C12 C14A 1.55(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15 H15 1.0000 . ?
C15 H15A 1.0000 . ?
C15 C16 1.555(3) . ?
C15 C20 1.549(5) . ?
C15 C20A 1.596(9) . ?
C15 B2 1.566(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C17 1.552(4) . ?
C16 C17A 1.282(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.469(4) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C18 1.655(11) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C18 C19 1.537(3) . ?
C19 H19 1.0000 . ?
C19 C22 1.543(3) . ?
C19 B2 1.577(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.533(6) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C20A C21A 1.563(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.543(5) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C21A C22 1.414(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
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 C9 C12 O2 -26.2(2) . . . . ?
O1 C9 C12 C13 -144.5(2) . . . . ?
O1 C9 C12 C14 86.6(2) . . . . ?
O1A C9 C12 O2A 8.8(16) . . . . ?
O1A C9 C12 C13A -100.6(14) . . . . ?
O1A C9 C12 C14A 142(2) . . . . ?
C1 C2 C3 C4 61.33(18) . . . . ?
C1 C2 C3 C8 -119.91(15) . . . . ?
C2 C1 B1 O1 -41.6(2) . . . . ?
C2 C1 B1 O1A -18.7(11) . . . . ?
C2 C1 B1 O2 138.1(2) . . . . ?
C2 C1 B1 O2A 158.1(14) . . . . ?
C2 C1 B2 C15 13.1(2) . . . . ?
C2 C1 B2 C19 -163.29(15) . . . . ?
C2 C3 C4 C5 178.15(14) . . . . ?
C2 C3 C8 C7 -178.95(15) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C4 C3 C8 C7 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
C9 O1 B1 O2 -10.3(3) . . . . ?
C9 O1 B1 C1 169.48(16) . . . . ?
C9 O1A B1 O2A 5.8(18) . . . . ?
C9 O1A B1 C1 -176.7(7) . . . . ?
C10 C9 C12 O2 86.3(2) . . . . ?
C10 C9 C12 C13 -32.1(2) . . . . ?
C10 C9 C12 C14 -160.99(19) . . . . ?
C10A C9 C12 O2A 153.0(17) . . . . ?
C10A C9 C12 C13A 43.6(15) . . . . ?
C10A C9 C12 C14A -74(2) . . . . ?
C11 C9 C12 O2 -146.1(2) . . . . ?
C11 C9 C12 C13 95.6(3) . . . . ?
C11 C9 C12 C14 -33.4(3) . . . . ?
C11A C9 C12 O2A -96.4(15) . . . . ?
C11A C9 C12 C13A 154.2(13) . . . . ?
C11A C9 C12 C14A 36(2) . . . . ?
C12 O2 B1 O1 -7.8(3) . . . . ?
C12 O2 B1 C1 172.40(16) . . . . ?
C12 O2A B1 O1A 1(2) . . . . ?
C12 O2A B1 C1 -176.7(8) . . . . ?
C15 C16 C17 C18 46.2(3) . . . . ?
C15 C16 C17A C18 -24.2(11) . . . . ?
C15 C20 C21 C22 52.9(7) . . . . ?
C15 C20A C21A C22 -59.3(14) . . . . ?
C16 C15 C20 C21 -117.5(5) . . . . ?
C16 C15 C20A C21A -48.8(13) . . . . ?
C16 C15 B2 C1 -110.72(18) . . . . ?
C16 C15 B2 C19 65.99(18) . . . . ?
C16 C17 C18 C19 -48.7(3) . . . . ?
C16 C17A C18 C19 20.2(10) . . . . ?
C17 C18 C19 C22 -63.6(2) . . . . ?
C17 C18 C19 B2 57.2(2) . . . . ?
C17A C18 C19 C22 -96.9(5) . . . . ?
C17A C18 C19 B2 23.9(5) . . . . ?
C18 C19 C22 C21 109.6(3) . . . . ?
C18 C19 C22 C21A 74.7(6) . . . . ?
C18 C19 B2 C1 108.77(18) . . . . ?
C18 C19 B2 C15 -68.11(19) . . . . ?
C20 C15 C16 C17 68.5(3) . . . . ?
C20 C15 B2 C1 134.9(3) . . . . ?
C20 C15 B2 C19 -48.4(3) . . . . ?
C20 C21 C22 C19 -47.7(6) . . . . ?
C20A C15 C16 C17A 97.6(8) . . . . ?
C20A C15 B2 C1 118.5(4) . . . . ?
C20A C15 B2 C19 -64.7(4) . . . . ?
C20A C21A C22 C19 44.5(12) . . . . ?
C22 C19 B2 C1 -129.67(17) . . . . ?
C22 C19 B2 C15 53.4(2) . . . . ?
B1 O1 C9 C10 -94.6(2) . . . . ?
B1 O1 C9 C11 147.6(2) . . . . ?
B1 O1 C9 C12 22.5(2) . . . . ?
B1 O1A C9 C10A -150.9(15) . . . . ?
B1 O1A C9 C11A 89.4(17) . . . . ?
B1 O1A C9 C12 -8.8(15) . . . . ?
B1 O2 C12 C9 21.1(3) . . . . ?
B1 O2 C12 C13 143.2(2) . . . . ?
B1 O2 C12 C14 -95.6(3) . . . . ?
B1 O2A C12 C9 -5.5(19) . . . . ?
B1 O2A C12 C13A 104.9(19) . . . . ?
B1 O2A C12 C14A -145.2(18) . . . . ?
B1 C1 C2 C3 -166.98(12) . . . . ?
B1 C1 B2 C15 -111.65(18) . . . . ?
B1 C1 B2 C19 71.97(18) . . . . ?
B2 C1 C2 C3 71.27(17) . . . . ?
B2 C1 B1 O1 86.3(2) . . . . ?
B2 C1 B1 O1A 109.2(11) . . . . ?
B2 C1 B1 O2 -94.0(2) . . . . ?
B2 C1 B1 O2A -74.0(14) . . . . ?
B2 C15 C16 C17 -52.3(2) . . . . ?
B2 C15 C16 C17A -16.6(7) . . . . ?
B2 C15 C20 C21 -3.9(7) . . . . ?
B2 C15 C20A C21A 66.9(11) . . . . ?
B2 C19 C22 C21 -6.6(3) . . . . ?
B2 C19 C22 C21A -41.4(6) . . . . ?
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
-0.9971 -0.0003 1.9981 -0.1426 -0.0059 -0.0727
0.9971 0.0003 -1.9981 0.1426 0.0059 0.0727
-1.0005 0.0008 -0.9983 0.0077 0.1399 -0.0066
1.0005 -0.0008 0.9983 -0.0077 -0.1399 0.0066
1.9994 0.9984 0.0003 -0.0209 -0.1668 0.2633
-0.9988 -0.9992 0.9980 0.0132 0.0270 -0.2567
