# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20191122b
_database_code_depnum_ccdc_archive 'CCDC 2174322'
loop_
_audit_author_name
_audit_author_address
'Guohua Hou'
;Beijing Normal University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_audit_creation_date             2019-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H28 B N O4'
_chemical_formula_sum            'C23 H28 B N O4'
_chemical_formula_weight         393.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1B1N1O1
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'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5661(2)
_cell_length_b                   12.0582(3)
_cell_length_c                   18.4149(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2124.16(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5970
_cell_measurement_theta_min      2.4150
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13039
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.777
_diffrn_reflns_theta_min         4.383
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  70.00   0.50    0.05    --   47.70 -99.00   9.00  132
  2  ω    -12.00  34.00   0.50    0.05    --   47.70 -27.00-175.00   92
  3  ω    -99.00 -34.00   0.50    0.05    -- -102.00 119.00-161.00  130
  4  ω     99.00 171.00   0.50    0.05    --  104.75  27.00 -13.00  144
  5  ω     53.00 106.00   0.50    0.05    --  104.75 -99.00   9.00  106
  6  ω    -23.00  25.00   0.50    0.05    --  -47.70  19.00  30.00   96
  7  ω    -27.00  27.00   0.50    0.05    --   47.70 -19.00  60.00  108
  8  ω    -64.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   70
  9  ω    -64.00 -32.00   0.50    0.05    -- -102.00  61.00 150.00   64
 10  ω   -169.00-144.00   0.50    0.05    -- -102.00-125.00 -30.00   50
 11  ω    -68.00 -29.00   0.50    0.05    -- -102.00  61.00-180.00   78
 12  ω    -99.00 -74.00   0.50    0.05    -- -102.00-125.00 -30.00   50
 13  ω     79.00 105.00   0.50    0.05    --  104.75 -77.00   0.00   52
 14  ω     32.00  57.00   0.50    0.05    --  104.75 -77.00   0.00   50
 15  ω    144.00 170.00   0.50    0.05    --  104.75 125.00-150.00   52
 16  ω     84.00 138.00   0.50    0.05    --  104.75 125.00-150.00  108
 17  ω     93.00 178.00   0.50    0.05    --  104.75  15.00  30.00  170
 18  ω     35.00  61.00   0.50    0.05    --  104.75 -61.00-180.00   52
 19  ω     45.00  71.00   0.50    0.05    --  104.75 -61.00 150.00   52
 20  ω     77.00 102.00   0.50    0.05    --  104.75 -94.00 -90.00   50
 21  ω    -20.00   5.00   0.50    0.05    --   47.70 -27.00-175.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0044562000
_diffrn_orient_matrix_UB_12      -0.1153621000
_diffrn_orient_matrix_UB_13      0.0357154000
_diffrn_orient_matrix_UB_21      -0.0553753000
_diffrn_orient_matrix_UB_22      0.0526959000
_diffrn_orient_matrix_UB_23      0.0706525000
_diffrn_orient_matrix_UB_31      -0.1511059000
_diffrn_orient_matrix_UB_32      -0.0159583000
_diffrn_orient_matrix_UB_33      -0.0269871000
_diffrn_oxdiff_digest_frames     
;
0100c7040edb84effe8b337515b0dcc998017564bb2
;
_diffrn_oxdiff_digest_hkl        
;
01facf6ab6464ba140ad58e04644665afb5551
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4161
_reflns_number_total             4240
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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)'
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4240
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.054
_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)+(0.0416P)²+1.2544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_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
2. Rigid bond restraints
 C18A, C19A, C20A, C21, C22, C23, N1, O1, O2, O3, O4, C19B, C18B, C20B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C18A \\sim C19A \\sim C20A \\sim C21 \\sim C22 \\sim C23 \\sim N1 \\sim O1
\\sim O2 \\sim O3 \\sim O4 \\sim C19B \\sim C18B \\sim C20B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C18B)=Sof(C20B)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C18A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C14(H14), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19A(H19A,H19B,H19C), C20A(H20A,H20B,H20C), C22(H22A,
 H22B,H22C), C23(H23A,H23B,H23C), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
B1 B 0.3288(3) 0.2560(2) 0.63036(16) 0.0239(5) Uani 1 1 d . . . . .
C1 C 0.1975(3) 0.7328(2) 0.42409(14) 0.0281(6) Uani 1 1 d . . . . .
H1 H 0.1145 0.7074 0.4445 0.034 Uiso 1 1 calc R . . . .
C2 C 0.1959(3) 0.8078(2) 0.36715(14) 0.0315(6) Uani 1 1 d . . . . .
H2 H 0.1110 0.8336 0.3492 0.038 Uiso 1 1 calc R . . . .
C3 C 0.3201(3) 0.8446(2) 0.33668(14) 0.0325(6) Uani 1 1 d . . . . .
H3 H 0.3186 0.8957 0.2988 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4454(3) 0.8054(2) 0.36260(15) 0.0304(6) Uani 1 1 d . . . . .
H4 H 0.5284 0.8291 0.3415 0.037 Uiso 1 1 calc R . . . .
C5 C 0.4493(3) 0.7311(2) 0.41990(14) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.5341 0.7050 0.4377 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3248(3) 0.69659(19) 0.44989(13) 0.0240(5) Uani 1 1 d . . . . .
C7 C 0.3192(3) 0.66094(18) 0.57457(13) 0.0216(5) Uani 1 1 d . . . . .
C8 C 0.2954(2) 0.60230(19) 0.70053(13) 0.0205(5) Uani 1 1 d . . . . .
C9 C 0.3249(3) 0.70615(19) 0.73113(13) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.3692 0.7603 0.7035 0.028 Uiso 1 1 calc R . . . .
C10 C 0.2880(3) 0.7281(2) 0.80247(14) 0.0272(5) Uani 1 1 d . . . . .
H10 H 0.3061 0.7978 0.8220 0.033 Uiso 1 1 calc R . . . .
C11 C 0.2248(3) 0.6482(2) 0.84508(15) 0.0292(6) Uani 1 1 d . . . . .
H11 H 0.1978 0.6642 0.8924 0.035 Uiso 1 1 calc R . . . .
C12 C 0.2025(3) 0.5434(2) 0.81584(14) 0.0268(5) Uani 1 1 d . . . . .
H12 H 0.1638 0.4883 0.8448 0.032 Uiso 1 1 calc R . . . .
C13 C 0.2370(2) 0.51911(19) 0.74389(14) 0.0222(5) Uani 1 1 d . . . . .
C14 C 0.2154(3) 0.40348(19) 0.71470(14) 0.0243(5) Uani 1 1 d . . . . .
H14 H 0.2238 0.3515 0.7554 0.029 Uiso 1 1 calc R . . . .
C15 C 0.0695(3) 0.3904(2) 0.68227(18) 0.0354(7) Uani 1 1 d . . . . .
H15A H 0.0007 0.4016 0.7195 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.0597 0.3172 0.6625 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.0565 0.4442 0.6445 0.053 Uiso 1 1 calc GR . . . .
C16 C 0.3340(3) 0.37855(19) 0.66073(14) 0.0237(5) Uani 1 1 d . . . . .
H16 H 0.4226 0.3871 0.6869 0.028 Uiso 1 1 calc R . . . .
C17 C 0.3336(3) 0.46217(19) 0.59896(14) 0.0288(6) Uani 1 1 d . . . . .
H17A H 0.4187 0.4539 0.5709 0.035 Uiso 1 1 calc R . . . .
H17B H 0.2552 0.4467 0.5671 0.035 Uiso 1 1 calc R . . . .
C18A C 0.3520(8) 0.1122(5) 0.5520(3) 0.0290(12) Uani 0.660(11) 1 d . U P A 1
C19A C 0.2405(9) 0.1212(5) 0.4939(3) 0.057(2) Uani 0.660(11) 1 d . U P A 1
H19A H 0.2784 0.1580 0.4521 0.086 Uiso 0.660(11) 1 calc GR . P A 1
H19B H 0.1627 0.1629 0.5123 0.086 Uiso 0.660(11) 1 calc GR . P A 1
H19C H 0.2097 0.0483 0.4804 0.086 Uiso 0.660(11) 1 calc GR . P A 1
C20A C 0.4759(7) 0.0478(4) 0.5229(3) 0.0435(15) Uani 0.660(11) 1 d . U P A 1
H20A H 0.4486 -0.0276 0.5139 0.065 Uiso 0.660(11) 1 calc GR . P A 1
H20B H 0.5503 0.0492 0.5579 0.065 Uiso 0.660(11) 1 calc GR . P A 1
H20C H 0.5073 0.0810 0.4784 0.065 Uiso 0.660(11) 1 calc GR . P A 1
C21 C 0.2993(3) 0.06881(19) 0.62870(14) 0.0242(5) Uani 1 1 d . U . . .
C22 C 0.1713(4) -0.0024(3) 0.6333(3) 0.0826(17) Uani 1 1 d . U . . .
H22A H 0.0915 0.0391 0.6172 0.124 Uiso 1 1 calc GR . . . .
H22B H 0.1574 -0.0254 0.6827 0.124 Uiso 1 1 calc GR . . . .
H22C H 0.1831 -0.0665 0.6030 0.124 Uiso 1 1 calc GR . . . .
C23 C 0.4159(4) 0.0120(3) 0.6670(2) 0.0552(10) Uani 1 1 d . U . . .
H23A H 0.4359 -0.0571 0.6432 0.083 Uiso 1 1 calc GR . . . .
H23B H 0.3896 -0.0019 0.7165 0.083 Uiso 1 1 calc GR . . . .
H23C H 0.4976 0.0583 0.6660 0.083 Uiso 1 1 calc GR . . . .
N1 N 0.3232(2) 0.57869(15) 0.62553(11) 0.0215(4) Uani 1 1 d . U . . .
O1 O 0.3290(2) 0.61762(13) 0.50634(9) 0.0298(4) Uani 1 1 d . U . . .
O2 O 0.3088(2) 0.75947(13) 0.58515(9) 0.0290(4) Uani 1 1 d . U . . .
O3 O 0.3782(4) 0.22575(17) 0.56558(13) 0.0688(10) Uani 1 1 d . U . . .
O4 O 0.2736(3) 0.17173(15) 0.66825(11) 0.0412(5) Uani 1 1 d . U . . .
C19B C 0.1321(19) 0.1159(9) 0.5292(8) 0.068(5) Uani 0.340(11) 1 d . U P A 2
H19D H 0.1006 0.0439 0.5142 0.102 Uiso 0.340(11) 1 calc GR . P A 2
H19E H 0.1231 0.1671 0.4896 0.102 Uiso 0.340(11) 1 calc GR . P A 2
H19F H 0.0764 0.1410 0.5694 0.102 Uiso 0.340(11) 1 calc GR . P A 2
C18B C 0.2836(18) 0.1092(10) 0.5522(7) 0.037(3) Uani 0.340(11) 1 d . U P A 2
C20B C 0.366(3) 0.0517(9) 0.4959(7) 0.083(7) Uani 0.340(11) 1 d . U P A 2
H20D H 0.4642 0.0603 0.5061 0.125 Uiso 0.340(11) 1 calc GR . P A 2
H20E H 0.3459 0.0831 0.4492 0.125 Uiso 0.340(11) 1 calc GR . P A 2
H20F H 0.3430 -0.0257 0.4957 0.125 Uiso 0.340(11) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
B1 C16 1.581(3) . ?
B1 O3 1.334(4) . ?
B1 O4 1.341(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C1 C6 1.378(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C6 O1 1.410(3) . ?
C7 N1 1.366(3) . ?
C7 O1 1.364(3) . ?
C7 O2 1.208(3) . ?
C8 C9 1.402(3) . ?
C8 C13 1.399(3) . ?
C8 N1 1.435(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(4) . ?
C13 C14 1.509(3) . ?
C14 H14 0.9800 . ?
C14 C15 1.526(4) . ?
C14 C16 1.538(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9800 . ?
C16 C17 1.520(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 N1 1.491(3) . ?
C18A C19A 1.515(8) . ?
C18A C20A 1.515(8) . ?
C18A C21 1.588(7) . ?
C18A O3 1.414(6) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C21 C22 1.497(4) . ?
C21 C23 1.487(4) . ?
C21 O4 1.460(3) . ?
C21 C18B 1.498(13) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O3 C18B 1.689(14) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C19B C18B 1.512(19) . ?
C18B C20B 1.478(18) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?

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
O3 B1 C16 124.1(2) . . ?
O3 B1 O4 113.4(2) . . ?
O4 B1 C16 122.5(2) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C6 C1 C2 118.6(2) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 O1 119.6(2) . . ?
C5 C6 C1 122.0(2) . . ?
C5 C6 O1 118.3(2) . . ?
O1 C7 N1 110.66(19) . . ?
O2 C7 N1 127.3(2) . . ?
O2 C7 O1 122.1(2) . . ?
C9 C8 N1 121.8(2) . . ?
C13 C8 C9 119.4(2) . . ?
C13 C8 N1 118.8(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C14 120.9(2) . . ?
C12 C13 C8 119.0(2) . . ?
C12 C13 C14 120.0(2) . . ?
C13 C14 H14 107.9 . . ?
C13 C14 C15 111.1(2) . . ?
C13 C14 C16 108.0(2) . . ?
C15 C14 H14 107.9 . . ?
C15 C14 C16 113.7(2) . . ?
C16 C14 H14 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
B1 C16 H16 107.5 . . ?
C14 C16 B1 112.8(2) . . ?
C14 C16 H16 107.5 . . ?
C17 C16 B1 110.8(2) . . ?
C17 C16 C14 110.6(2) . . ?
C17 C16 H16 107.5 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
N1 C17 C16 112.3(2) . . ?
N1 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
C19A C18A C21 115.4(5) . . ?
C20A C18A C19A 109.7(5) . . ?
C20A C18A C21 113.2(4) . . ?
O3 C18A C19A 100.4(5) . . ?
O3 C18A C20A 114.8(5) . . ?
O3 C18A C21 102.6(4) . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18A C20A H20A 109.5 . . ?
C18A C20A H20B 109.5 . . ?
C18A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22 C21 C18A 119.9(4) . . ?
C22 C21 C18B 99.1(7) . . ?
C23 C21 C18A 109.6(3) . . ?
C23 C21 C22 108.8(3) . . ?
C23 C21 C18B 132.1(7) . . ?
O4 C21 C18A 102.5(3) . . ?
O4 C21 C22 108.8(2) . . ?
O4 C21 C23 106.4(2) . . ?
O4 C21 C18B 100.1(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 N1 C8 120.80(18) . . ?
C7 N1 C17 117.43(19) . . ?
C8 N1 C17 121.00(19) . . ?
C7 O1 C6 114.73(17) . . ?
B1 O3 C18A 111.1(3) . . ?
B1 O3 C18B 99.7(5) . . ?
B1 O4 C21 108.6(2) . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
C21 C18B O3 94.6(7) . . ?
C21 C18B C19B 112.1(11) . . ?
C19B C18B O3 120.7(9) . . ?
C20B C18B C21 117.0(11) . . ?
C20B C18B O3 101.9(11) . . ?
C20B C18B C19B 110.0(13) . . ?
C18B C20B H20D 109.5 . . ?
C18B C20B H20E 109.5 . . ?
C18B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20191125a
_database_code_depnum_ccdc_archive 'CCDC 2174323'
loop_
_audit_author_name
_audit_author_address
'Guohua Hou'
;Beijing Normal University
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 B O3'
_chemical_formula_sum            'C18 H27 B O3'
_chemical_formula_weight         302.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1B1
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3311(2)
_cell_length_b                   13.3436(3)
_cell_length_c                   17.2766(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.05(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4103
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      72.0830
_cell_measurement_theta_min      4.1760
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.077
_diffrn_reflns_theta_min         4.186
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -18.00   1.00    1.00    --  -41.49 -37.00  90.00   94
  2  ω    -37.00 -11.00   1.00    1.00    --  -41.49 -19.00 -60.00   26
  3  ω   -118.00 -40.00   1.00    1.00    --  -41.49 -19.00 -60.00   78
  4  ω     32.00 115.00   1.00    1.00    --  104.69 -45.00 120.00   83
  5  ω     79.00 175.00   1.00    1.00    --  104.69  61.00 -90.00   96
  6  ω     99.00 170.00   1.00    1.00    --  104.69 125.00-180.00   71
  7  ω    144.00 171.00   1.00    1.00    --  104.69 125.00 -90.00   27
  8  ω     97.00 143.00   1.00    1.00    --  104.69 119.00 119.00   46
  9  ω     47.00 110.00   1.00    1.00    --  104.69-125.00   0.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453863000
_diffrn_orient_matrix_UB_12      0.0914866000
_diffrn_orient_matrix_UB_13      -0.0509091000
_diffrn_orient_matrix_UB_21      -0.2034117000
_diffrn_orient_matrix_UB_22      -0.0115262000
_diffrn_orient_matrix_UB_23      0.0203774000
_diffrn_orient_matrix_UB_31      0.0260950000
_diffrn_orient_matrix_UB_32      0.0695212000
_diffrn_orient_matrix_UB_33      0.0703437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3110
_reflns_number_total             3222
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.061
_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)+(0.0507P)²+0.5381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0999
_refine_special_details          ?
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
B1 B 0.7853(4) 0.56240(17) 0.55125(13) 0.0178(5) Uani 1 1 d . . . . .
C1 C 0.7237(3) 0.78763(15) 0.73158(12) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.7347(3) 0.85798(15) 0.79208(12) 0.0183(4) Uani 1 1 d . . . . .
C3 C 0.5864(3) 0.86709(16) 0.84062(12) 0.0205(5) Uani 1 1 d . . . . .
H3 H 0.5892 0.9139 0.8805 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4325(3) 0.80743(16) 0.83090(12) 0.0208(5) Uani 1 1 d . . . . .
H4 H 0.3338 0.8152 0.8642 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4241(3) 0.73589(16) 0.77182(12) 0.0191(5) Uani 1 1 d . . . . .
C6 C 0.5725(3) 0.72534(15) 0.72074(11) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.9035(3) 0.92056(17) 0.80179(13) 0.0237(5) Uani 1 1 d . . . . .
H7A H 1.0054 0.8778 0.8131 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.8861 0.9670 0.8436 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.9269 0.9569 0.7549 0.036 Uiso 1 1 calc GR . . . .
C8 C 0.2548(3) 0.67219(18) 0.76562(14) 0.0240(5) Uani 1 1 d . . . . .
H8A H 0.1989 0.6663 0.8157 0.036 Uiso 1 1 calc GR . . . .
H8B H 0.2870 0.6068 0.7470 0.036 Uiso 1 1 calc GR . . . .
H8C H 0.1706 0.7029 0.7303 0.036 Uiso 1 1 calc GR . . . .
C9 C 0.5699(3) 0.64862(15) 0.65502(12) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.5242 0.5852 0.6761 0.021 Uiso 1 1 calc R . . . .
C10 C 0.4409(3) 0.68120(17) 0.58988(13) 0.0234(5) Uani 1 1 d . . . . .
H10A H 0.3234 0.6968 0.6112 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.4288 0.6278 0.5530 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.4897 0.7394 0.5646 0.035 Uiso 1 1 calc GR . . . .
C11 C 0.7656(3) 0.63059(16) 0.62553(12) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.8314 0.5966 0.6673 0.021 Uiso 1 1 calc R . . . .
C12 C 0.8589(3) 0.73098(17) 0.61370(12) 0.0202(5) Uani 1 1 d . . . . .
H12A H 0.9793 0.7200 0.5921 0.024 Uiso 1 1 calc R . . . .
H12B H 0.7893 0.7703 0.5769 0.024 Uiso 1 1 calc R . . . .
C13 C 0.7219(4) 0.45410(16) 0.45338(13) 0.0224(5) Uani 1 1 d . . . . .
C14 C 0.5995(4) 0.5119(2) 0.39744(16) 0.0407(7) Uani 1 1 d . . . . .
H14A H 0.6244 0.4908 0.3454 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.6230 0.5823 0.4023 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.4739 0.4987 0.4095 0.061 Uiso 1 1 calc GR . . . .
C15 C 0.6907(4) 0.34234(19) 0.44610(17) 0.0383(7) Uani 1 1 d . . . . .
H15A H 0.5633 0.3280 0.4526 0.057 Uiso 1 1 calc GR . . . .
H15B H 0.7594 0.3079 0.4852 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.7295 0.3202 0.3959 0.057 Uiso 1 1 calc GR . . . .
C16 C 0.9239(3) 0.48783(17) 0.44782(13) 0.0233(5) Uani 1 1 d . . . . .
C17 C 1.0574(4) 0.4101(2) 0.47932(15) 0.0357(6) Uani 1 1 d . . . . .
H17A H 1.0126 0.3844 0.5276 0.054 Uiso 1 1 calc GR . . . .
H17B H 1.1743 0.4408 0.4873 0.054 Uiso 1 1 calc GR . . . .
H17C H 1.0693 0.3562 0.4429 0.054 Uiso 1 1 calc GR . . . .
C18 C 0.9866(4) 0.5229(2) 0.36892(15) 0.0338(6) Uani 1 1 d . . . . .
H18A H 0.9772 0.4686 0.3327 0.051 Uiso 1 1 calc GR . . . .
H18B H 1.1112 0.5447 0.3720 0.051 Uiso 1 1 calc GR . . . .
H18C H 0.9112 0.5775 0.3521 0.051 Uiso 1 1 calc GR . . . .
O1 O 0.8755(2) 0.78590(11) 0.68460(9) 0.0203(4) Uani 1 1 d . . . . .
O2 O 0.6721(2) 0.48562(12) 0.53187(9) 0.0248(4) Uani 1 1 d . . . . .
O3 O 0.9284(2) 0.57318(12) 0.50139(9) 0.0262(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
B1 C11 1.580(3) . ?
B1 O2 1.360(3) . ?
B1 O3 1.365(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.398(3) . ?
C1 O1 1.378(3) . ?
C2 C3 1.379(3) . ?
C2 C7 1.502(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 C6 1.408(3) . ?
C5 C8 1.508(3) . ?
C6 C9 1.529(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9 0.9800 . ?
C9 C10 1.533(3) . ?
C9 C11 1.542(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C12 1.518(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 O1 1.433(2) . ?
C13 C14 1.528(4) . ?
C13 C15 1.514(3) . ?
C13 C16 1.551(3) . ?
C13 O2 1.466(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.526(4) . ?
C16 C18 1.513(3) . ?
C16 O3 1.468(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
O2 B1 C11 125.3(2) . . ?
O2 B1 O3 113.11(18) . . ?
O3 B1 C11 121.5(2) . . ?
C6 C1 C2 122.8(2) . . ?
O1 C1 C2 113.72(19) . . ?
O1 C1 C6 123.47(18) . . ?
C1 C2 C7 120.1(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 C7 122.19(19) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 C8 118.2(2) . . ?
C6 C5 C8 122.35(19) . . ?
C1 C6 C5 117.98(19) . . ?
C1 C6 C9 120.50(19) . . ?
C5 C6 C9 121.5(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9 107.8 . . ?
C6 C9 C10 111.30(17) . . ?
C6 C9 C11 109.77(18) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C11 112.07(18) . . ?
C11 C9 H9 107.8 . . ?
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 . . ?
B1 C11 H11 106.7 . . ?
C9 C11 B1 116.32(18) . . ?
C9 C11 H11 106.7 . . ?
C12 C11 B1 110.96(17) . . ?
C12 C11 C9 109.03(17) . . ?
C12 C11 H11 106.7 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O1 C12 C11 112.00(17) . . ?
O1 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C14 C13 C16 112.1(2) . . ?
C15 C13 C14 110.8(2) . . ?
C15 C13 C16 115.2(2) . . ?
O2 C13 C14 107.11(19) . . ?
O2 C13 C15 108.78(19) . . ?
O2 C13 C16 102.22(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 113.1(2) . . ?
C18 C16 C13 115.8(2) . . ?
C18 C16 C17 109.7(2) . . ?
O3 C16 C13 101.95(18) . . ?
O3 C16 C17 106.76(19) . . ?
O3 C16 C18 108.77(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 O1 C12 116.33(17) . . ?
B1 O2 C13 106.99(17) . . ?
B1 O3 C16 107.42(17) . . ?

_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.803
