#------------------------------------------------------------------------------
#$Date: 2021-11-03 22:29:04 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270238 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519099.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_4519099
loop_
_publ_author_name
'Simlandy, Amit Kumar'
'Lyu, Mao-Yun'
'Brown, M. Kevin'
_publ_section_title
;
 Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to
 Highly Substituted Spiro[3.n]alkanes
;
_journal_issue                   20
_journal_name_full               'ACS Catalysis'
_journal_page_first              12815
_journal_page_last               12820
_journal_paper_doi               10.1021/acscatal.1c03491
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C24 H36 B N O4'
_chemical_formula_sum            'C24 H36 B N O4'
_chemical_formula_weight         413.35
_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     intrinsic
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                112.8490(10)
_cell_angle_beta                 92.5750(10)
_cell_angle_gamma                92.4840(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9066(4)
_cell_length_b                   11.0766(4)
_cell_length_c                   11.6203(5)
_cell_measurement_reflns_used    9203
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.78
_cell_volume                     1171.31(8)
_computing_cell_refinement       'SAINT V8.38A (BrukerNano, 2017)'
_computing_data_collection       'BIS v6.2.9 (BrukerNano, 2018)'
_computing_data_reduction        'SAINT V8.38A (BrukerNano, 2017)'
_computing_molecular_graphics
;
C. B. HÃ¼bschle, G. M. Sheldrick and B. Dittrich
"ShelXle: a Qt graphical user interface for SHELXL"
J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_publication_material  'APEX3 v2018.1-0 (BrukerNano, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
'1 deg frames measured for 2 s at detector distance of 40 mm'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         1.906
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
L. Krause, R. Herbst-Irmer, G.M. Sheldrick, D. Stalke,
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination"
J. Appl. Cryst. (2015), 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0458
_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)+(0.0487P)²+0.3842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3432
_reflns_number_total             4810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03491_si_002.cif
_cod_data_source_block           21173
_cod_database_code               4519099
_shelx_shelxl_version_number     2018/3
_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_min   0.977
_shelx_estimated_absorpt_t_max   0.989
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
O1 O 0.63228(12) 0.53378(11) 0.33336(11) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.58908(13) 0.31577(11) 0.21296(13) 0.0427(3) Uani 1 1 d . . . . .
O3 O -0.01970(11) 0.86700(11) 0.09704(10) 0.0324(3) Uani 1 1 d . . . . .
O4 O -0.02924(11) 0.84621(11) 0.28466(10) 0.0317(3) Uani 1 1 d . . . . .
N1 N 0.45408(14) 0.46906(13) 0.19653(14) 0.0351(3) Uani 1 1 d . . . . .
B1 B 0.01931(18) 0.79970(19) 0.16835(18) 0.0292(4) Uani 1 1 d . . . . .
C1 C 0.29444(15) 0.59274(15) 0.14201(15) 0.0278(4) Uani 1 1 d . . . . .
C2 C 0.42179(16) 0.60506(15) 0.22641(16) 0.0304(4) Uani 1 1 d . . . . .
H2A H 0.496759 0.655035 0.207468 0.036 Uiso 1 1 calc R U . . .
H2AB H 0.403820 0.649318 0.315817 0.036 Uiso 1 1 calc R U . . .
C3 C 0.36480(18) 0.37466(17) 0.09485(18) 0.0403(5) Uani 1 1 d . . . . .
H3A H 0.292968 0.334049 0.127384 0.048 Uiso 1 1 calc R U . . .
H3AB H 0.416163 0.304799 0.035963 0.048 Uiso 1 1 calc R U . . .
C4 C 0.30624(17) 0.46099(16) 0.03324(17) 0.0355(4) Uani 1 1 d . . . . .
H4A H 0.216381 0.423856 -0.009784 0.043 Uiso 1 1 calc R U . . .
H4AB H 0.367248 0.470677 -0.028253 0.043 Uiso 1 1 calc R U . . .
C5 C 0.26202(16) 0.70452(15) 0.09767(15) 0.0283(4) Uani 1 1 d . . . . .
H5 H 0.277276 0.678226 0.006891 0.034 Uiso 1 1 calc R U . . .
C6 C 0.10836(16) 0.67942(16) 0.11720(16) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.064091 0.615340 0.036138 0.036 Uiso 1 1 calc R U . . .
C7 C 0.15400(16) 0.60282(17) 0.19718(17) 0.0339(4) Uani 1 1 d . . . . .
H7A H 0.103116 0.516968 0.174590 0.041 Uiso 1 1 calc R U . . .
H7AB H 0.156702 0.654856 0.288505 0.041 Uiso 1 1 calc R U . . .
C8 C 0.56112(17) 0.42967(16) 0.24528(16) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.75717(18) 0.51355(18) 0.39517(18) 0.0385(4) Uani 1 1 d . . . . .
C10 C 0.7251(2) 0.4308(3) 0.4688(2) 0.0671(7) Uani 1 1 d . . . . .
H10A H 0.652604 0.468771 0.523906 0.101 Uiso 1 1 calc R U . . .
H10B H 0.806181 0.428793 0.519349 0.101 Uiso 1 1 calc R U . . .
H10C H 0.695623 0.341282 0.410978 0.101 Uiso 1 1 calc R U . . .
C11 C 0.8583(2) 0.4530(3) 0.2994(2) 0.0621(6) Uani 1 1 d . . . . .
H11A H 0.946047 0.453545 0.342141 0.093 Uiso 1 1 calc R U . . .
H11B H 0.868158 0.503729 0.247112 0.093 Uiso 1 1 calc R U . . .
H11C H 0.826512 0.362336 0.246701 0.093 Uiso 1 1 calc R U . . .
C12 C 0.8071(3) 0.6515(2) 0.4796(3) 0.0773(8) Uani 1 1 d . . . . .
H12A H 0.891072 0.649399 0.526460 0.116 Uiso 1 1 calc R U . . .
H12B H 0.738342 0.692004 0.538239 0.116 Uiso 1 1 calc R U . . .
H12C H 0.824344 0.702938 0.428951 0.116 Uiso 1 1 calc R U . . .
C13 C 0.32478(15) 0.84056(16) 0.17412(15) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.38132(16) 0.91442(17) 0.11325(17) 0.0333(4) Uani 1 1 d . . . . .
H14 H 0.382808 0.876842 0.024657 0.040 Uiso 1 1 calc R U . . .
C15 C 0.43535(18) 1.04111(18) 0.17849(19) 0.0398(4) Uani 1 1 d . . . . .
H15 H 0.471161 1.090499 0.134535 0.048 Uiso 1 1 calc R U . . .
C16 C 0.43751(18) 1.09611(18) 0.30700(19) 0.0412(5) Uani 1 1 d . . . . .
H16 H 0.475669 1.183007 0.351964 0.049 Uiso 1 1 calc R U . . .
C17 C 0.38390(18) 1.02436(17) 0.37044(18) 0.0387(4) Uani 1 1 d . . . . .
H17 H 0.385829 1.061734 0.459250 0.046 Uiso 1 1 calc R U . . .
C18 C 0.32730(17) 0.89791(16) 0.30461(16) 0.0336(4) Uani 1 1 d . . . . .
H18 H 0.289724 0.849634 0.348862 0.040 Uiso 1 1 calc R U . . .
C19 C -0.08137(17) 0.98446(16) 0.18030(16) 0.0311(4) Uani 1 1 d . . . . .
C20 C -0.12835(17) 0.94130(16) 0.28494(16) 0.0311(4) Uani 1 1 d . . . . .
C21 C 0.0302(2) 1.09463(18) 0.2249(2) 0.0446(5) Uani 1 1 d . . . . .
H21A H 0.103124 1.071995 0.271277 0.067 Uiso 1 1 calc R U . . .
H21B H -0.006849 1.176269 0.279748 0.067 Uiso 1 1 calc R U . . .
H21C H 0.066063 1.106514 0.152541 0.067 Uiso 1 1 calc R U . . .
C22 C -0.19410(19) 1.01753(19) 0.10732(17) 0.0406(4) Uani 1 1 d . . . . .
H22A H -0.243547 1.088637 0.164763 0.061 Uiso 1 1 calc R U . . .
H22B H -0.256292 0.939789 0.065130 0.061 Uiso 1 1 calc R U . . .
H22C H -0.155438 1.045564 0.044821 0.061 Uiso 1 1 calc R U . . .
C23 C -0.1234(2) 1.05044(19) 0.41375(17) 0.0448(5) Uani 1 1 d . . . . .
H23A H -0.150364 1.014309 0.474659 0.067 Uiso 1 1 calc R U . . .
H23B H -0.185496 1.116674 0.413068 0.067 Uiso 1 1 calc R U . . .
H23C H -0.030997 1.091059 0.436989 0.067 Uiso 1 1 calc R U . . .
C24 C -0.26572(17) 0.86622(18) 0.25390(18) 0.0395(4) Uani 1 1 d . . . . .
H24A H -0.280062 0.824374 0.313173 0.059 Uiso 1 1 calc R U . . .
H24B H -0.269265 0.798785 0.168656 0.059 Uiso 1 1 calc R U . . .
H24C H -0.336635 0.926967 0.259816 0.059 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
B B 0.0013 0.0007 '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_
_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
C8 O1 C9 119.61(13) . . ?
B1 O3 C19 106.79(13) . . ?
B1 O4 C20 106.48(13) . . ?
C8 N1 C2 125.95(14) . . ?
C8 N1 C3 120.89(14) . . ?
C2 N1 C3 112.85(13) . . ?
O4 B1 O3 113.57(15) . . ?
O4 B1 C6 124.57(16) . . ?
O3 B1 C6 121.85(15) . . ?
C4 C1 C2 102.91(13) . . ?
C4 C1 C7 112.06(13) . . ?
C2 C1 C7 119.33(14) . . ?
C4 C1 C5 112.77(14) . . ?
C2 C1 C5 120.52(13) . . ?
C7 C1 C5 89.48(12) . . ?
N1 C2 C1 103.85(13) . . ?
N1 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
N1 C2 H2AB 111.0 . . ?
C1 C2 H2AB 111.0 . . ?
H2A C2 H2AB 109.0 . . ?
N1 C3 C4 101.91(13) . . ?
N1 C3 H3A 111.4 . . ?
C4 C3 H3A 111.4 . . ?
N1 C3 H3AB 111.4 . . ?
C4 C3 H3AB 111.4 . . ?
H3A C3 H3AB 109.3 . . ?
C3 C4 C1 104.10(14) . . ?
C3 C4 H4A 110.9 . . ?
C1 C4 H4A 110.9 . . ?
C3 C4 H4AB 110.9 . . ?
C1 C4 H4AB 110.9 . . ?
H4A C4 H4AB 109.0 . . ?
C13 C5 C1 117.90(13) . . ?
C13 C5 C6 115.89(13) . . ?
C1 C5 C6 87.87(12) . . ?
C13 C5 H5 111.1 . . ?
C1 C5 H5 111.1 . . ?
C6 C5 H5 111.1 . . ?
C7 C6 B1 122.40(15) . . ?
C7 C6 C5 88.64(12) . . ?
B1 C6 C5 118.63(13) . . ?
C7 C6 H6 108.5 . . ?
B1 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C6 C7 C1 89.17(12) . . ?
C6 C7 H7A 113.8 . . ?
C1 C7 H7A 113.8 . . ?
C6 C7 H7AB 113.8 . . ?
C1 C7 H7AB 113.8 . . ?
H7A C7 H7AB 111.0 . . ?
O2 C8 N1 124.12(16) . . ?
O2 C8 O1 125.35(16) . . ?
N1 C8 O1 110.53(14) . . ?
O1 C9 C12 102.65(14) . . ?
O1 C9 C11 109.93(16) . . ?
C12 C9 C11 110.01(19) . . ?
O1 C9 C10 110.14(15) . . ?
C12 C9 C10 111.7(2) . . ?
C11 C9 C10 112.02(19) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.64(15) . . ?
C14 C13 C5 119.23(15) . . ?
C18 C13 C5 123.12(15) . . ?
C15 C14 C13 121.51(17) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C16 C15 C14 120.17(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.69(17) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.08(18) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.89(16) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
O3 C19 C22 109.13(13) . . ?
O3 C19 C21 106.40(13) . . ?
C22 C19 C21 110.02(15) . . ?
O3 C19 C20 101.97(12) . . ?
C22 C19 C20 114.91(14) . . ?
C21 C19 C20 113.68(15) . . ?
O4 C20 C23 109.20(14) . . ?
O4 C20 C24 106.11(13) . . ?
C23 C20 C24 110.27(15) . . ?
O4 C20 C19 102.28(12) . . ?
C23 C20 C19 114.69(15) . . ?
C24 C20 C19 113.56(14) . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.350(2) . ?
O1 C9 1.472(2) . ?
O2 C8 1.217(2) . ?
O3 B1 1.367(2) . ?
O3 C19 1.4651(19) . ?
O4 B1 1.365(2) . ?
O4 C20 1.4699(19) . ?
N1 C8 1.347(2) . ?
N1 C2 1.462(2) . ?
N1 C3 1.462(2) . ?
B1 C6 1.562(2) . ?
C1 C4 1.529(2) . ?
C1 C2 1.530(2) . ?
C1 C7 1.548(2) . ?
C1 C5 1.555(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C13 1.509(2) . ?
C5 C6 1.578(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.548(2) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C9 C12 1.506(3) . ?
C9 C11 1.507(3) . ?
C9 C10 1.510(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.389(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C22 1.514(2) . ?
C19 C21 1.523(2) . ?
C19 C20 1.551(2) . ?
C20 C23 1.512(2) . ?
C20 C24 1.516(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10C O2 0.98 2.40 2.971(3) 116.9 . yes
C11 H11C O2 0.98 2.37 2.942(3) 116.7 . yes
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
C20 O4 B1 O3 9.61(18) . . . . ?
C20 O4 B1 C6 -169.04(15) . . . . ?
C19 O3 B1 O4 10.51(18) . . . . ?
C19 O3 B1 C6 -170.80(14) . . . . ?
C8 N1 C2 C1 178.07(16) . . . . ?
C3 N1 C2 C1 4.43(19) . . . . ?
C4 C1 C2 N1 -25.69(17) . . . . ?
C7 C1 C2 N1 99.12(16) . . . . ?
C5 C1 C2 N1 -152.28(14) . . . . ?
C8 N1 C3 C4 -155.21(16) . . . . ?
C2 N1 C3 C4 18.79(19) . . . . ?
N1 C3 C4 C1 -34.36(17) . . . . ?
C2 C1 C4 C3 37.67(17) . . . . ?
C7 C1 C4 C3 -91.77(16) . . . . ?
C5 C1 C4 C3 169.07(13) . . . . ?
C4 C1 C5 C13 -144.31(14) . . . . ?
C2 C1 C5 C13 -22.4(2) . . . . ?
C7 C1 C5 C13 101.90(15) . . . . ?
C4 C1 C5 C6 97.34(14) . . . . ?
C2 C1 C5 C6 -140.73(15) . . . . ?
C7 C1 C5 C6 -16.45(12) . . . . ?
O4 B1 C6 C7 -1.8(3) . . . . ?
O3 B1 C6 C7 179.62(15) . . . . ?
O4 B1 C6 C5 -110.16(19) . . . . ?
O3 B1 C6 C5 71.3(2) . . . . ?
C13 C5 C6 C7 -103.71(15) . . . . ?
C1 C5 C6 C7 16.46(12) . . . . ?
C13 C5 C6 B1 23.0(2) . . . . ?
C1 C5 C6 B1 143.15(15) . . . . ?
B1 C6 C7 C1 -140.06(15) . . . . ?
C5 C6 C7 C1 -16.52(12) . . . . ?
C4 C1 C7 C6 -97.68(15) . . . . ?
C2 C1 C7 C6 142.03(14) . . . . ?
C5 C1 C7 C6 16.77(12) . . . . ?
C2 N1 C8 O2 -175.65(16) . . . . ?
C3 N1 C8 O2 -2.5(3) . . . . ?
C2 N1 C8 O1 3.9(2) . . . . ?
C3 N1 C8 O1 177.09(15) . . . . ?
C9 O1 C8 O2 2.2(3) . . . . ?
C9 O1 C8 N1 -177.39(15) . . . . ?
C8 O1 C9 C12 177.30(18) . . . . ?
C8 O1 C9 C11 60.3(2) . . . . ?
C8 O1 C9 C10 -63.6(2) . . . . ?
C1 C5 C13 C14 135.73(15) . . . . ?
C6 C5 C13 C14 -122.14(16) . . . . ?
C1 C5 C13 C18 -45.3(2) . . . . ?
C6 C5 C13 C18 56.8(2) . . . . ?
C18 C13 C14 C15 -1.5(2) . . . . ?
C5 C13 C14 C15 177.51(15) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C14 C13 C18 C17 0.3(2) . . . . ?
C5 C13 C18 C17 -178.71(16) . . . . ?
B1 O3 C19 C22 -146.51(15) . . . . ?
B1 O3 C19 C21 94.81(16) . . . . ?
B1 O3 C19 C20 -24.55(16) . . . . ?
B1 O4 C20 C23 -145.97(15) . . . . ?
B1 O4 C20 C24 95.19(16) . . . . ?
B1 O4 C20 C19 -24.06(16) . . . . ?
O3 C19 C20 O4 29.20(15) . . . . ?
C22 C19 C20 O4 147.10(14) . . . . ?
C21 C19 C20 O4 -84.88(16) . . . . ?
O3 C19 C20 C23 147.27(14) . . . . ?
C22 C19 C20 C23 -94.83(18) . . . . ?
C21 C19 C20 C23 33.2(2) . . . . ?
O3 C19 C20 C24 -84.67(16) . . . . ?
C22 C19 C20 C24 33.2(2) . . . . ?
C21 C19 C20 C24 161.24(15) . . . . ?
