#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/41/4134181.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_4134181
loop_
_publ_author_name
'Patel, Harshal D.'
'Tran, Thanh-Huyen'
'Sumby, Christopher J.'
'Pašteka, Lukáš F'
'Fallon, Thomas'
_publ_section_title
;
 Boronate Ester Bullvalenes.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3680
_journal_page_last               3685
_journal_paper_doi               10.1021/jacs.9b12930
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C22 H18'
_chemical_formula_sum            'C22 H18'
_chemical_formula_weight         282.36
_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     direct
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.776(5)
_cell_angle_beta                 90.715(5)
_cell_angle_gamma                96.917(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9975(3)
_cell_length_b                   10.0967(5)
_cell_length_c                   13.1405(8)
_cell_measurement_reflns_used    5460
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0570
_cell_measurement_theta_min      3.8620
_cell_volume                     746.78(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -2.00  88.00   1.00    6.00    --   18.95  57.00-150.00   90
  2  ω     -2.00  88.00   1.00    6.00    --   18.95  57.00  60.00   90
  3  ω    -50.00  39.00   1.00    6.00    --   18.95 -57.00 -60.00   89
  4  ω    -50.00  39.00   1.00    6.00    --   18.95 -57.00  60.00   89
  5  ω    -25.00  22.00   1.00    6.00    --  -19.50 -99.00  90.00   47
  6  ω    -25.00  22.00   1.00    6.00    --  -19.50 -99.00-150.00   47
  7  ω     35.00  95.00   1.00    6.00    --   18.95 178.00 -60.00   60
  8  ω     -2.00  88.00   1.00    6.00    --   18.95  57.00 -30.00   90
  9  ω    -50.00  39.00   1.00    6.00    --   18.95 -57.00 -90.00   89
 10  ω    -74.00   6.00   1.00    6.00    --  -19.50 121.00  80.00   80
 11  ω    -94.00 -14.00   1.00    6.00    --  -19.50 152.00-119.00   80
 12  ω    -50.00  39.00   1.00    6.00    --   18.95 -57.00-180.00   89
 13  ω     35.00  89.00   1.00    6.00    --   18.95 178.00 120.00   54
 14  ω    -88.00   2.00   1.00    6.00    --  -19.50 -57.00  60.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713526000
_diffrn_orient_matrix_UB_12      -0.0088449000
_diffrn_orient_matrix_UB_13      -0.0436951000
_diffrn_orient_matrix_UB_21      -0.0954983000
_diffrn_orient_matrix_UB_22      -0.0151703000
_diffrn_orient_matrix_UB_23      -0.0362146000
_diffrn_orient_matrix_UB_31      0.0048961000
_diffrn_orient_matrix_UB_32      0.0727596000
_diffrn_orient_matrix_UB_33      0.0062725000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16532
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.275
_diffrn_reflns_theta_min         3.427
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0445
_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)+(0.0437P)²+0.2767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3073
_reflns_number_total             3635
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b12930_si_002.cif
_cod_data_source_block
C:\Users\chris\DOCUME~1\X-RAYC~1\Fallon\14AREP~1\HP322
_cod_depositor_comments
'Adding full bibliography for 4134168--4134181.cif.'
_cod_database_code               4134181
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         C22H18
_chemical_oxdiff_usercomment
'colourless plate (from rod) 0.47 x 0.38 x 0.12'
_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   0.992
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_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 1.057
_oxdiff_exptl_absorpt_empirical_full_min 0.958
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
C1 C 0.05994(19) 0.30610(11) 0.20635(9) 0.0167(2) Uani 1 1 d . . . . .
H1 H 0.0392 0.3116 0.2829 0.020 Uiso 1 1 calc R . . . .
C2 C 0.16153(18) 0.17120(11) 0.15101(9) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.20854(18) 0.13393(12) 0.04680(9) 0.0176(2) Uani 1 1 d . . . . .
H3 H 0.2719 0.0485 0.0187 0.021 Uiso 1 1 calc R . . . .
C4 C 0.1729(2) 0.21057(13) -0.02852(9) 0.0198(2) Uani 1 1 d . . . . .
H4 H 0.2217 0.1640 -0.1026 0.024 Uiso 1 1 calc R . . . .
C5 C 0.2002(2) 0.37235(13) 0.00517(10) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.2634 0.4109 -0.0512 0.025 Uiso 1 1 calc R . . . .
C6 C 0.27350(19) 0.46088(12) 0.11564(10) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.3685 0.5462 0.1232 0.022 Uiso 1 1 calc R . . . .
C7 C 0.22213(18) 0.43535(11) 0.20692(9) 0.0159(2) Uani 1 1 d . . . . .
C8 C -0.16964(19) 0.30037(12) 0.15480(10) 0.0211(3) Uani 1 1 d . . . . .
H8 H -0.2958 0.3038 0.1982 0.025 Uiso 1 1 calc R . . . .
C9 C -0.2054(2) 0.29077(13) 0.05256(11) 0.0241(3) Uani 1 1 d . . . . .
H9 H -0.3570 0.2856 0.0282 0.029 Uiso 1 1 calc R . . . .
C10 C -0.0337(2) 0.28736(13) -0.02634(10) 0.0227(3) Uani 1 1 d . . . . .
H10 H -0.0948 0.2810 -0.0991 0.027 Uiso 1 1 calc R . . . .
C11 C 0.19451(19) 0.07787(11) 0.21550(9) 0.0161(2) Uani 1 1 d . . . . .
C12 C 0.3848(2) 0.00862(12) 0.20741(10) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.4971 0.0217 0.1599 0.025 Uiso 1 1 calc R . . . .
C13 C 0.4118(2) -0.07922(13) 0.26803(11) 0.0260(3) Uani 1 1 d . . . . .
H13 H 0.5425 -0.1254 0.2617 0.031 Uiso 1 1 calc R . . . .
C14 C 0.2500(2) -0.09997(14) 0.33751(11) 0.0282(3) Uani 1 1 d . . . . .
H14 H 0.2692 -0.1599 0.3789 0.034 Uiso 1 1 calc R . . . .
C15 C 0.0597(2) -0.03246(13) 0.34620(10) 0.0257(3) Uani 1 1 d . . . . .
H15 H -0.0527 -0.0467 0.3933 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0326(2) 0.05595(12) 0.28623(10) 0.0200(2) Uani 1 1 d . . . . .
H16 H -0.0979 0.1023 0.2933 0.024 Uiso 1 1 calc R . . . .
C21 C 0.32450(19) 0.53071(11) 0.31241(9) 0.0171(2) Uani 1 1 d . . . . .
C22 C 0.2013(2) 0.56095(12) 0.40472(10) 0.0226(3) Uani 1 1 d . . . . .
H22 H 0.0494 0.5189 0.4002 0.027 Uiso 1 1 calc R . . . .
C23 C 0.2972(3) 0.65148(13) 0.50295(11) 0.0292(3) Uani 1 1 d . . . . .
H23 H 0.2102 0.6712 0.5647 0.035 Uiso 1 1 calc R . . . .
C24 C 0.5183(2) 0.71321(13) 0.51155(11) 0.0300(3) Uani 1 1 d . . . . .
H24 H 0.5835 0.7750 0.5789 0.036 Uiso 1 1 calc R . . . .
C25 C 0.6436(2) 0.68412(13) 0.42104(11) 0.0265(3) Uani 1 1 d . . . . .
H25 H 0.7956 0.7262 0.4263 0.032 Uiso 1 1 calc R . . . .
C26 C 0.5485(2) 0.59380(12) 0.32254(10) 0.0212(3) Uani 1 1 d . . . . .
H26 H 0.6366 0.5745 0.2611 0.025 Uiso 1 1 calc R . . . .
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'
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
C2 C1 C7 110.29(9) . . ?
C8 C1 C2 110.45(9) . . ?
C8 C1 C7 112.99(9) . . ?
C3 C2 C1 121.79(10) . . ?
C3 C2 C11 120.89(10) . . ?
C11 C2 C1 117.23(10) . . ?
C2 C3 C4 127.18(11) . . ?
C3 C4 C5 123.12(10) . . ?
C3 C4 C10 122.10(10) . . ?
C10 C4 C5 59.77(8) . . ?
C6 C5 C4 121.40(10) . . ?
C6 C5 C10 123.55(10) . . ?
C10 C5 C4 60.07(8) . . ?
C7 C6 C5 127.55(11) . . ?
C6 C7 C1 121.43(10) . . ?
C6 C7 C21 120.90(10) . . ?
C21 C7 C1 117.66(10) . . ?
C9 C8 C1 123.93(11) . . ?
C8 C9 C10 126.35(11) . . ?
C5 C10 C4 60.16(8) . . ?
C9 C10 C4 121.97(10) . . ?
C9 C10 C5 121.99(11) . . ?
C12 C11 C2 121.66(10) . . ?
C12 C11 C16 117.97(11) . . ?
C16 C11 C2 120.36(10) . . ?
C13 C12 C11 120.77(11) . . ?
C14 C13 C12 120.55(12) . . ?
C13 C14 C15 119.41(12) . . ?
C14 C15 C16 120.21(12) . . ?
C15 C16 C11 121.07(11) . . ?
C22 C21 C7 121.29(10) . . ?
C22 C21 C26 117.74(11) . . ?
C26 C21 C7 120.97(10) . . ?
C23 C22 C21 121.04(12) . . ?
C24 C23 C22 120.51(12) . . ?
C23 C24 C25 119.34(12) . . ?
C24 C25 C26 120.41(12) . . ?
C25 C26 C21 120.96(12) . . ?
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
C1 C2 1.5259(15) . ?
C1 C7 1.5288(15) . ?
C1 C8 1.5134(16) . ?
C2 C3 1.3416(16) . ?
C2 C11 1.4832(15) . ?
C3 C4 1.4668(16) . ?
C4 C5 1.5360(17) . ?
C4 C10 1.5347(16) . ?
C5 C6 1.4676(17) . ?
C5 C10 1.5301(16) . ?
C6 C7 1.3376(16) . ?
C7 C21 1.4842(16) . ?
C8 C9 1.3282(19) . ?
C9 C10 1.4659(18) . ?
C11 C12 1.3965(16) . ?
C11 C16 1.3996(16) . ?
C12 C13 1.3906(17) . ?
C13 C14 1.3841(19) . ?
C14 C15 1.3862(19) . ?
C15 C16 1.3888(17) . ?
C21 C22 1.3960(17) . ?
C21 C26 1.4013(16) . ?
C22 C23 1.3884(18) . ?
C23 C24 1.383(2) . ?
C24 C25 1.384(2) . ?
C25 C26 1.3889(18) . ?
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
C1 C2 C3 C4 -0.16(18) . . . . ?
C1 C2 C11 C12 -140.96(11) . . . . ?
C1 C2 C11 C16 39.56(14) . . . . ?
C1 C7 C21 C22 -38.14(15) . . . . ?
C1 C7 C21 C26 142.03(11) . . . . ?
C1 C8 C9 C10 -1.48(19) . . . . ?
C2 C1 C7 C6 66.33(14) . . . . ?
C2 C1 C7 C21 -112.58(11) . . . . ?
C2 C1 C8 C9 -61.90(15) . . . . ?
C2 C3 C4 C5 34.85(18) . . . . ?
C2 C3 C4 C10 -37.67(18) . . . . ?
C2 C11 C12 C13 -179.55(11) . . . . ?
C2 C11 C16 C15 179.21(11) . . . . ?
C3 C2 C11 C12 42.46(16) . . . . ?
C3 C2 C11 C16 -137.03(12) . . . . ?
C3 C4 C5 C6 2.56(17) . . . . ?
C3 C4 C5 C10 -110.75(13) . . . . ?
C3 C4 C10 C5 112.40(12) . . . . ?
C3 C4 C10 C9 1.18(17) . . . . ?
C4 C5 C6 C7 -36.22(18) . . . . ?
C4 C5 C10 C9 111.18(13) . . . . ?
C5 C4 C10 C9 -111.22(13) . . . . ?
C5 C6 C7 C1 -3.60(19) . . . . ?
C5 C6 C7 C21 175.28(11) . . . . ?
C6 C5 C10 C4 -109.86(12) . . . . ?
C6 C5 C10 C9 1.32(18) . . . . ?
C6 C7 C21 C22 142.94(12) . . . . ?
C6 C7 C21 C26 -36.89(16) . . . . ?
C7 C1 C2 C3 -63.09(14) . . . . ?
C7 C1 C2 C11 120.36(10) . . . . ?
C7 C1 C8 C9 62.18(15) . . . . ?
C7 C21 C22 C23 -179.27(11) . . . . ?
C7 C21 C26 C25 179.36(10) . . . . ?
C8 C1 C2 C3 62.53(14) . . . . ?
C8 C1 C2 C11 -114.02(11) . . . . ?
C8 C1 C7 C6 -57.84(14) . . . . ?
C8 C1 C7 C21 123.25(11) . . . . ?
C8 C9 C10 C4 36.99(19) . . . . ?
C8 C9 C10 C5 -35.45(19) . . . . ?
C10 C4 C5 C6 113.30(13) . . . . ?
C10 C5 C6 C7 36.52(18) . . . . ?
C11 C2 C3 C4 176.27(11) . . . . ?
C11 C12 C13 C14 0.15(19) . . . . ?
C12 C11 C16 C15 -0.29(17) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C11 0.55(19) . . . . ?
C16 C11 C12 C13 -0.05(17) . . . . ?
C21 C22 C23 C24 -0.40(19) . . . . ?
C22 C21 C26 C25 -0.47(17) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 -0.05(19) . . . . ?
C24 C25 C26 C21 0.22(18) . . . . ?
C26 C21 C22 C23 0.56(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336156
