#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:11:07 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571947.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_1571947
loop_
_publ_author_name
'Arnold, Robert E.'
'Saska, Jan'
'Mesquita-Ribeiro, Raquel'
'Dajas-Bailador, Federico'
'Taylor, Laurence'
'Lewis, William'
'Argent, Stephen'
'Shao, Huiling'
'Houk, Kendall N.'
'Denton, Ross M.'
_publ_section_title
;
 Total synthesis, biological evaluation and biosynthetic re-evaluation of
 Illicium-derived neolignans.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              11783
_journal_page_last               11793
_journal_paper_doi               10.1039/d4sc03232b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H18 B2 O4'
_chemical_formula_sum            'C18 H18 B2 O4'
_chemical_formula_weight         319.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.804(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.4184(9)
_cell_length_b                   4.96092(16)
_cell_length_c                   21.7474(7)
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1530
_cell_measurement_theta_min      4.5360
_cell_volume                     3317.96(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  34.00   1.00   20.00    --  -38.50  38.00 120.00   84
  2  ω    -90.00   2.00   1.00   20.00    --  -38.50 120.00 -54.00   92
  3  ω    -36.00  80.00   1.00   20.00    --   42.83 -19.00 -90.00  116
  4  ω     33.00 122.00   1.00   80.00    --  104.50-125.00 -90.00   89
  5  ω     33.00  98.00   1.00   80.00    --  104.50 -45.00  90.00   65
  6  ω     31.00 136.00   1.00   80.00    --  104.50 -77.00 -60.00  105
  7  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00 -60.00   61
  8  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00  30.00   61
  9  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00-180.00   61
 10  ω     73.00 178.00   1.00   80.00    --  104.50  77.00  60.00  105
 11  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00 -30.00   61
 12  ω     16.00 113.00   1.00   20.00    --   42.83  57.00 120.00   97
 13  ω     16.00 113.00   1.00   20.00    --   42.83  57.00-120.00   97
 14  ω     11.00 117.00   1.00   20.00    --   42.83  77.00   0.00  106
 15  ω     81.00 178.00   1.00   80.00    --  104.50  30.00-120.00   97
 16  ω     81.00 178.00   1.00   80.00    --  104.50  30.00 150.00   97
 17  ω     77.00 175.00   1.00   80.00    --  104.50  61.00  30.00   98
 18  ω     80.00 176.00   1.00   80.00    --  104.50  45.00 -90.00   96
 19  ω     23.00 109.00   1.00   80.00    --  104.50 -94.00  90.00   86
 20  ω     59.00 178.00   1.00   80.00    --  104.50  15.00   0.00  119
 21  ω   -110.00 -55.00   1.00   20.00    --  -38.50-154.00  64.00   55
 22  ω    -94.00  -2.00   1.00   20.00    --  -38.50 125.00-180.00   92
 23  ω     11.00 117.00   1.00   20.00    --   42.83  77.00 -90.00  106
 24  ω     80.00 105.00   1.00   80.00    --  104.50  45.00-180.00   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054633000
_diffrn_orient_matrix_UB_12      0.2908389000
_diffrn_orient_matrix_UB_13      0.0219773000
_diffrn_orient_matrix_UB_21      -0.0494110000
_diffrn_orient_matrix_UB_22      -0.0190106000
_diffrn_orient_matrix_UB_23      -0.0254186000
_diffrn_orient_matrix_UB_31      -0.0061681000
_diffrn_orient_matrix_UB_32      -0.1068536000
_diffrn_orient_matrix_UB_33      0.0641253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.746
_diffrn_reflns_theta_min         4.154
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0835
_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)+(0.0859P)²+24.1703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2607
_refine_ls_wR_factor_ref         0.2630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           25
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_original_cell_volume        3317.97(19)
_cod_database_code               1571947
_nottingham_internal_coll_name   REARDH
_nottingham_internal_coll_number 17457
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 80.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/01/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 23/01/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 23/1/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 23/1/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 13/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/2/2018
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C18 H18 B2 O4'
_chemical_oxdiff_usercomment
'REARDH #17457 GVB-1442 IN FOMBLIN FILM ON MICROMOUNT FOR REA/RD'
_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   0.987
_shelx_estimated_absorpt_t_min   0.792
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 O(H) groups
2. Others
 Sof(H14C)=Sof(H14D)=Sof(H16C)=Sof(H16D)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15)=Sof(H16A)=Sof(H16B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C15(H15), C18(H18), C20(H20), C21(H21), C23(H23),
 C15A(H15A)
3.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C24(H24A,H24B)
;
_olex2_date_sample_data_collection 2018-01-19
_olex2_date_sample_submission    2018-01-18
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
_olex2_submission_original_sample_id RA-195-001
_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 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.523
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.63036(8) 0.6427(5) 0.57819(11) 0.0274(6) Uani 1 1 d . . . . .
B2 B 0.66719(13) 0.4983(9) 0.57576(19) 0.0259(8) Uani 1 1 d . . . . .
O3 O 0.69031(8) 0.5427(5) 0.52931(11) 0.0261(6) Uani 1 1 d . . . . .
B4 B 0.67754(14) 0.7353(9) 0.48244(19) 0.0275(9) Uani 1 1 d . . . . .
C5 C 0.63644(11) 0.9018(7) 0.48614(17) 0.0260(8) Uani 1 1 d . . . . .
C6 C 0.61476(11) 0.8404(7) 0.53416(17) 0.0258(8) Uani 1 1 d . . . . .
C7 C 0.68250(11) 0.2766(7) 0.62623(16) 0.0256(8) Uani 1 1 d . . . . .
C8 C 0.71732(11) 0.1047(7) 0.62326(16) 0.0254(7) Uani 1 1 d . . . . .
C9 C 0.73037(12) -0.0943(8) 0.66808(18) 0.0299(8) Uani 1 1 d . . . . .
H9 H 0.753973 -0.209829 0.665086 0.036 Uiso 1 1 calc R . . . .
C10 C 0.70881(12) -0.1232(8) 0.71703(18) 0.0322(9) Uani 1 1 d . . . . .
H10 H 0.717760 -0.259176 0.747717 0.039 Uiso 1 1 calc R . . . .
C11 C 0.67391(13) 0.0455(9) 0.72201(18) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.66121(12) 0.2392(8) 0.67576(17) 0.0307(8) Uani 1 1 d . . . . .
H12 H 0.637005 0.350732 0.678042 0.037 Uiso 1 1 calc R . . . .
O13 O 0.74021(9) 0.1224(6) 0.57568(14) 0.0360(7) Uani 1 1 d . . . . .
H13 H 0.7271(17) 0.261(12) 0.548(2) 0.054 Uiso 1 1 d R . . . .
C14 C 0.64987(16) 0.0071(13) 0.7750(2) 0.0543(14) Uani 1 1 d . . . . .
H14A H 0.666130 -0.123656 0.805362 0.065 Uiso 0.870(14) 1 calc R . P A 1
H14B H 0.649437 0.181044 0.797186 0.065 Uiso 0.870(14) 1 calc R . P A 1
H14C H 0.645012 -0.189060 0.778241 0.065 Uiso 0.130(14) 1 calc R . P A 2
H14D H 0.670188 0.060866 0.814115 0.065 Uiso 0.130(14) 1 calc R . P A 2
C15 C 0.6059(2) -0.0868(13) 0.7552(3) 0.0516(19) Uani 0.870(14) 1 d . . P A 1
H15 H 0.602096 -0.257477 0.734944 0.062 Uiso 0.870(14) 1 calc R . P A 1
C16 C 0.57002(17) 0.0411(16) 0.7623(2) 0.0675(17) Uani 1 1 d . . . . .
H16A H 0.572065 0.212354 0.782181 0.081 Uiso 0.870(14) 1 calc R . P A 1
H16B H 0.542347 -0.038831 0.747413 0.081 Uiso 0.870(14) 1 calc R . P A 1
H16C H 0.563860 -0.139550 0.748831 0.081 Uiso 0.130(14) 1 calc R . P A 2
H16D H 0.546959 0.159802 0.765980 0.081 Uiso 0.130(14) 1 calc R . P A 2
O17 O 0.69953(10) 0.7679(6) 0.43614(13) 0.0382(7) Uani 1 1 d . . . . .
H17 H 0.7186(18) 0.648(12) 0.435(3) 0.057 Uiso 1 1 d R . . . .
C18 C 0.61811(12) 1.0994(8) 0.44245(17) 0.0279(8) Uani 1 1 d . . . . .
H18 H 0.632465 1.145079 0.409444 0.033 Uiso 1 1 calc R . . . .
C19 C 0.57968(12) 1.2298(8) 0.44607(17) 0.0292(8) Uani 1 1 d . . . . .
C20 C 0.55926(12) 1.1602(8) 0.49495(19) 0.0330(9) Uani 1 1 d . . . . .
H20 H 0.532908 1.248121 0.497998 0.040 Uiso 1 1 calc R . . . .
C21 C 0.57616(12) 0.9667(8) 0.53936(18) 0.0313(8) Uani 1 1 d . . . . .
H21 H 0.561763 0.921869 0.572370 0.038 Uiso 1 1 calc R . . . .
C22 C 0.56024(13) 1.4410(8) 0.3979(2) 0.0356(9) Uani 1 1 d . . . . .
H22A H 0.562605 1.619905 0.418426 0.043 Uiso 1 1 calc R . . . .
H22B H 0.577373 1.446604 0.364408 0.043 Uiso 1 1 calc R . . . .
C23 C 0.51414(15) 1.3894(10) 0.3689(2) 0.0445(11) Uani 1 1 d . . . . .
H23 H 0.507225 1.220975 0.348497 0.053 Uiso 1 1 calc R . . . .
C24 C 0.48227(16) 1.5572(13) 0.3691(3) 0.0606(15) Uani 1 1 d . . . . .
H24A H 0.487866 1.727716 0.389047 0.073 Uiso 1 1 calc R . . . .
H24B H 0.453437 1.509086 0.349429 0.073 Uiso 1 1 calc R . . . .
C15A C 0.6115(11) 0.129(8) 0.7760(15) 0.041(11) Uani 0.130(14) 1 d . . P A 2
H15A H 0.614267 0.311931 0.788990 0.049 Uiso 0.130(14) 1 calc R . 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 0.0181 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 -1 0.0148
-1 0 1 0.0308
-1 -2 5 0.1554
-2 3 -1 0.1651
-1 0 0 0.0010
1 0 0 0.0177
1 -3 -1 0.1738
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
B2 O1 C6 121.6(3) . . ?
O1 B2 O3 121.4(3) . . ?
O1 B2 C7 118.9(3) . . ?
O3 B2 C7 119.8(3) . . ?
B2 O3 B4 122.0(3) . . ?
O3 B4 C5 116.5(3) . . ?
O17 B4 O3 121.0(3) . . ?
O17 B4 C5 122.5(3) . . ?
C6 C5 B4 117.6(3) . . ?
C6 C5 C18 117.7(3) . . ?
C18 C5 B4 124.6(3) . . ?
O1 C6 C5 120.9(3) . . ?
O1 C6 C21 116.9(3) . . ?
C21 C6 C5 122.1(3) . . ?
C8 C7 B2 121.9(3) . . ?
C12 C7 B2 120.7(3) . . ?
C12 C7 C8 117.3(3) . . ?
C9 C8 C7 121.5(3) . . ?
O13 C8 C7 121.9(3) . . ?
O13 C8 C9 116.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.3(4) . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 C14 121.6(4) . . ?
C7 C12 H12 118.6 . . ?
C11 C12 C7 122.7(4) . . ?
C11 C12 H12 118.6 . . ?
C8 O13 H13 107(3) . . ?
C11 C14 H14A 108.7 . . ?
C11 C14 H14B 108.7 . . ?
C11 C14 H14C 106.6 . . ?
C11 C14 H14D 106.6 . . ?
H14A C14 H14B 107.6 . . ?
H14C C14 H14D 106.6 . . ?
C15 C14 C11 114.2(4) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C15A C14 C11 122.8(14) . . ?
C15A C14 H14C 106.6 . . ?
C15A C14 H14D 106.6 . . ?
C14 C15 H15 116.7 . . ?
C16 C15 C14 126.5(6) . . ?
C16 C15 H15 116.7 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
H16C C16 H16D 120.0 . . ?
C15A C16 H16C 120.0 . . ?
C15A C16 H16D 120.0 . . ?
B4 O17 H17 114(4) . . ?
C5 C18 H18 119.0 . . ?
C19 C18 C5 121.9(3) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 C22 121.0(3) . . ?
C20 C19 C22 121.0(3) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 C19 122.1(4) . . ?
C21 C20 H20 118.9 . . ?
C6 C21 H21 120.9 . . ?
C20 C21 C6 118.1(3) . . ?
C20 C21 H21 120.9 . . ?
C19 C22 H22A 108.9 . . ?
C19 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 C19 113.3(4) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23 117.5 . . ?
C24 C23 C22 125.0(5) . . ?
C24 C23 H23 117.5 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C14 C15A H15A 113.7 . . ?
C16 C15A C14 133(3) . . ?
C16 C15A H15A 113.7 . . ?
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 B2 1.371(5) . ?
O1 C6 1.388(4) . ?
B2 O3 1.377(5) . ?
B2 C7 1.559(5) . ?
O3 B4 1.395(5) . ?
B4 C5 1.549(5) . ?
B4 O17 1.342(5) . ?
C5 C6 1.392(5) . ?
C5 C18 1.404(5) . ?
C6 C21 1.390(5) . ?
C7 C8 1.399(5) . ?
C7 C12 1.392(5) . ?
C8 C9 1.389(5) . ?
C8 O13 1.378(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(6) . ?
C11 C12 1.389(6) . ?
C11 C14 1.513(6) . ?
C12 H12 0.9500 . ?
O13 H13 0.95(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C15 1.438(8) . ?
C14 C15A 1.35(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.330(8) . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C16 H16C 0.9500 . ?
C16 H16D 0.9500 . ?
C16 C15A 1.35(3) . ?
O17 H17 0.85(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(5) . ?
C19 C20 1.393(5) . ?
C19 C22 1.519(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.479(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.303(7) . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C15A H15A 0.9500 . ?
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
O13 H13 O3 0.95(6) 1.81(6) 2.679(4) 152(5) . yes
O17 H17 O13 0.85(6) 1.91(6) 2.756(4) 174(5) 7_656 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
O1 B2 O3 B4 -0.2(6) . . . . ?
O1 B2 C7 C8 173.9(3) . . . . ?
O1 B2 C7 C12 -4.9(5) . . . . ?
O1 C6 C21 C20 -178.4(3) . . . . ?
B2 O1 C6 C5 -0.8(5) . . . . ?
B2 O1 C6 C21 177.3(3) . . . . ?
B2 O3 B4 C5 1.3(5) . . . . ?
B2 O3 B4 O17 -177.3(4) . . . . ?
B2 C7 C8 C9 -179.2(3) . . . . ?
B2 C7 C8 O13 0.3(5) . . . . ?
B2 C7 C12 C11 -179.6(4) . . . . ?
O3 B2 C7 C8 -5.1(5) . . . . ?
O3 B2 C7 C12 176.1(3) . . . . ?
O3 B4 C5 C6 -2.2(5) . . . . ?
O3 B4 C5 C18 -178.4(3) . . . . ?
B4 C5 C6 O1 2.0(5) . . . . ?
B4 C5 C6 C21 -176.1(4) . . . . ?
B4 C5 C18 C19 175.8(4) . . . . ?
C5 C6 C21 C20 -0.2(6) . . . . ?
C5 C18 C19 C20 0.2(6) . . . . ?
C5 C18 C19 C22 -179.4(4) . . . . ?
C6 O1 B2 O3 -0.2(5) . . . . ?
C6 O1 B2 C7 -179.2(3) . . . . ?
C6 C5 C18 C19 -0.4(6) . . . . ?
C7 B2 O3 B4 178.9(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C7 C12 C11 1.6(6) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C9 C10 C11 C14 178.5(4) . . . . ?
C10 C11 C12 C7 -1.9(6) . . . . ?
C10 C11 C14 C15 -112.0(5) . . . . ?
C10 C11 C14 C15A -168(2) . . . . ?
C11 C14 C15 C16 -118.6(6) . . . . ?
C11 C14 C15A C16 101(3) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
C12 C7 C8 O13 179.1(3) . . . . ?
C12 C11 C14 C15 65.3(7) . . . . ?
C12 C11 C14 C15A 10(2) . . . . ?
O13 C8 C9 C10 -180.0(3) . . . . ?
C14 C11 C12 C7 -179.3(4) . . . . ?
O17 B4 C5 C6 176.4(4) . . . . ?
O17 B4 C5 C18 0.2(6) . . . . ?
C18 C5 C6 O1 178.4(3) . . . . ?
C18 C5 C6 C21 0.4(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C18 C19 C22 C23 127.6(4) . . . . ?
C19 C20 C21 C6 0.0(6) . . . . ?
C19 C22 C23 C24 123.2(5) . . . . ?
C20 C19 C22 C23 -52.0(5) . . . . ?
C22 C19 C20 C21 179.5(4) . . . . ?
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
0.9988 -0.0003 -0.9973 -0.0275 -0.0240 -0.0701
-0.9988 0.0003 0.9973 0.0275 0.0240 0.0701
-0.9951 -1.9985 5.0124 -0.4656 -0.0402 0.5411
-2.0069 2.9993 -1.0218 0.8608 0.0681 -0.3736
-0.9975 0.0002 -0.0048 0.0054 0.0494 0.0058
0.9975 -0.0002 0.0048 -0.0054 -0.0494 -0.0058
1.0119 -2.9993 -0.9872 -0.8995 0.0321 0.2509
