#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/43/4134395.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_4134395
loop_
_publ_author_name
'Hari, Durga Prasad'
'Abell, Joseph C.'
'Fasano, Valerio'
'Aggarwal, Varinder K.'
_publ_section_title
;
 Ring-Expansion Induced 1,2-Metalate Rearrangements: Highly
 Diastereoselective Synthesis of Cyclobutyl Boronic Esters.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5515
_journal_page_last               5520
_journal_paper_doi               10.1021/jacs.0c00813
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C17 H34 B N O2, H2 O'
_chemical_formula_sum            'C17 H36 B N O3'
_chemical_formula_weight         313.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.686(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2394(13)
_cell_length_b                   16.054(2)
_cell_length_c                   13.4313(18)
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.70
_cell_measurement_theta_min      2.28
_cell_volume                     1927.2(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1213
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22565
_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         25.349
_diffrn_reflns_theta_min         2.016
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0735 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.8283. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0548
_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)+(0.0609P)²+0.2140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2108
_reflns_number_total             3522
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c00813_si_003.cif
_cod_data_source_block           testm1
_cod_depositor_comments
'Adding full bibliography for 4134395--4134396.cif.'
_cod_original_cell_volume        1927.1(5)
_cod_database_code               4134395
_shelx_shelxl_version_number     2017/1
_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   0.993
_shelx_estimated_absorpt_t_min   0.974
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36417(19) 0.83107(10) 0.31876(10) 0.0193(4) Uani 1 1 d . . . . .
O2 O 0.35015(18) 0.73940(10) 0.45256(10) 0.0194(4) Uani 1 1 d . . . . .
N1 N 0.4779(2) 0.59800(12) 0.32683(13) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.4542(3) 0.68942(15) 0.29586(16) 0.0205(6) Uani 1 1 d . . . . .
H1A H 0.359232 0.693107 0.241588 0.025 Uiso 1 1 calc R . . . .
H1B H 0.535320 0.705501 0.263663 0.025 Uiso 1 1 calc R . . . .
C2 C 0.5904(3) 0.58716(16) 0.42981(15) 0.0214(6) Uani 1 1 d . . . . .
H2A H 0.612003 0.527021 0.441271 0.026 Uiso 1 1 calc R . . . .
H2B H 0.544457 0.606741 0.484653 0.026 Uiso 1 1 calc R . . . .
C3 C 0.7372(3) 0.63304(16) 0.44029(17) 0.0226(6) Uani 1 1 d . . . . .
H3 H 0.755171 0.638382 0.370212 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7401(3) 0.71983(15) 0.48604(16) 0.0209(6) Uani 1 1 d . . . . .
H4 H 0.840015 0.744670 0.487910 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6193(3) 0.78904(15) 0.44558(16) 0.0173(6) Uani 1 1 d . . . . .
C6 C 0.6391(3) 0.81409(16) 0.56111(16) 0.0239(6) Uani 1 1 d . . . . .
H6A H 0.706029 0.862472 0.582948 0.029 Uiso 1 1 calc R . . . .
H6B H 0.543293 0.821815 0.580257 0.029 Uiso 1 1 calc R . . . .
C7 C 0.7144(3) 0.72972(16) 0.59485(16) 0.0248(6) Uani 1 1 d . . . . .
H7A H 0.646299 0.687451 0.611703 0.030 Uiso 1 1 calc R . . . .
H7B H 0.807955 0.733981 0.650321 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3354(3) 0.56046(17) 0.33745(18) 0.0277(7) Uani 1 1 d . . . . .
H8A H 0.299947 0.590836 0.389984 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.352338 0.501958 0.357937 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.260128 0.563854 0.271440 0.042 Uiso 1 1 calc GR . . . .
C9 C 0.5284(3) 0.54958(16) 0.24646(17) 0.0296(7) Uani 1 1 d . . . . .
H9A H 0.452627 0.553576 0.180725 0.044 Uiso 1 1 calc GR . . . .
H9B H 0.542372 0.491040 0.267393 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.623281 0.572425 0.238661 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.8632(3) 0.58009(17) 0.5066(2) 0.0309(7) Uani 1 1 d . . . . .
H10A H 0.959081 0.608598 0.513802 0.046 Uiso 1 1 calc GR . . . .
H10B H 0.865913 0.525867 0.473577 0.046 Uiso 1 1 calc GR . . . .
H10C H 0.845153 0.571918 0.574724 0.046 Uiso 1 1 calc GR . . . .
C11 C 0.6771(3) 0.85542(17) 0.38305(17) 0.0254(6) Uani 1 1 d . . . . .
H11A H 0.780440 0.869943 0.418209 0.038 Uiso 1 1 calc GR . . . .
H11B H 0.614035 0.905210 0.376600 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.673743 0.833505 0.314402 0.038 Uiso 1 1 calc GR . . . .
C12 C 0.2494(3) 0.86108(16) 0.36330(16) 0.0205(6) Uani 1 1 d . . . . .
C13 C 0.2103(3) 0.78294(16) 0.42083(16) 0.0203(6) Uani 1 1 d . . . . .
C14 C 0.3107(3) 0.93345(17) 0.43588(17) 0.0273(7) Uani 1 1 d . . . . .
H14A H 0.392503 0.913428 0.492448 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.230773 0.956207 0.463800 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.348218 0.977052 0.397862 0.041 Uiso 1 1 calc GR . . . .
C15 C 0.1198(3) 0.89331(18) 0.27762(18) 0.0304(7) Uani 1 1 d . . . . .
H15A H 0.151836 0.943017 0.246595 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.035395 0.907532 0.306250 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.088975 0.850104 0.224964 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.1568(3) 0.80400(17) 0.51644(17) 0.0273(6) Uani 1 1 d . . . . .
H16A H 0.131594 0.752500 0.547442 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.068085 0.839703 0.497036 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.236445 0.833306 0.566235 0.041 Uiso 1 1 calc GR . . . .
C17 C 0.0946(3) 0.72633(18) 0.35074(18) 0.0296(7) Uani 1 1 d . . . . .
H17A H 0.124176 0.715929 0.286766 0.044 Uiso 1 1 calc GR . . . .
H17B H -0.003605 0.753513 0.334828 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.089030 0.673328 0.385788 0.044 Uiso 1 1 calc GR . . . .
B1 B 0.4478(3) 0.76068(18) 0.38330(18) 0.0180(6) Uani 1 1 d . . . . .
O3 O 0.3710(2) 0.62332(11) 0.61463(12) 0.0298(5) Uani 1 1 d . . . . .
H3A H 0.363386 0.645464 0.672211 0.045 Uiso 1 1 d G . . . .
H3B H 0.367673 0.665477 0.573380 0.045 Uiso 1 1 d G . . . .
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
C12 O1 B1 109.76(17) . . ?
C13 O2 B1 110.16(17) . . ?
C2 N1 C1 112.16(17) . . ?
C8 N1 C1 110.3(2) . . ?
C8 N1 C2 106.56(18) . . ?
C8 N1 C9 107.70(19) . . ?
C9 N1 C1 110.62(17) . . ?
C9 N1 C2 109.36(19) . . ?
N1 C1 H1A 107.3 . . ?
N1 C1 H1B 107.3 . . ?
N1 C1 B1 120.07(17) . . ?
H1A C1 H1B 106.9 . . ?
B1 C1 H1A 107.3 . . ?
B1 C1 H1B 107.3 . . ?
N1 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
N1 C2 C3 114.77(19) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C2 C3 H3 108.2 . . ?
C2 C3 C4 113.9(2) . . ?
C2 C3 C10 108.3(2) . . ?
C4 C3 H3 108.2 . . ?
C4 C3 C10 109.9(2) . . ?
C10 C3 H3 108.2 . . ?
C3 C4 H4 107.3 . . ?
C3 C4 C5 124.8(2) . . ?
C3 C4 C7 119.0(2) . . ?
C5 C4 H4 107.3 . . ?
C7 C4 H4 107.3 . . ?
C7 C4 C5 89.35(18) . . ?
C4 C5 B1 119.0(2) . . ?
C6 C5 C4 86.83(17) . . ?
C6 C5 B1 115.2(2) . . ?
C11 C5 C4 111.4(2) . . ?
C11 C5 C6 113.2(2) . . ?
C11 C5 B1 109.60(18) . . ?
C5 C6 H6A 113.7 . . ?
C5 C6 H6B 113.7 . . ?
H6A C6 H6B 110.9 . . ?
C7 C6 C5 89.78(17) . . ?
C7 C6 H6A 113.7 . . ?
C7 C6 H6B 113.7 . . ?
C4 C7 H7A 113.9 . . ?
C4 C7 H7B 113.9 . . ?
C6 C7 C4 88.76(17) . . ?
C6 C7 H7A 113.9 . . ?
C6 C7 H7B 113.9 . . ?
H7A C7 H7B 111.1 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C13 103.03(19) . . ?
O1 C12 C14 109.2(2) . . ?
O1 C12 C15 108.83(17) . . ?
C14 C12 C13 112.90(18) . . ?
C15 C12 C13 114.2(2) . . ?
C15 C12 C14 108.4(2) . . ?
O2 C13 C12 103.57(19) . . ?
O2 C13 C16 108.49(18) . . ?
O2 C13 C17 109.2(2) . . ?
C16 C13 C12 113.8(2) . . ?
C16 C13 C17 108.9(2) . . ?
C17 C13 C12 112.65(19) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 B1 C1 102.43(16) . . ?
O1 B1 C5 111.6(2) . . ?
O2 B1 O1 103.1(2) . . ?
O2 B1 C1 114.9(2) . . ?
O2 B1 C5 113.61(17) . . ?
C1 B1 C5 110.3(2) . . ?
H3A O3 H3B 104.5 . . ?
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 C12 1.427(3) . ?
O1 B1 1.512(3) . ?
O2 C13 1.435(3) . ?
O2 B1 1.491(3) . ?
N1 C1 1.526(3) . ?
N1 C2 1.515(3) . ?
N1 C8 1.487(3) . ?
N1 C9 1.498(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 B1 1.651(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.520(3) . ?
C3 C10 1.531(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.571(3) . ?
C4 C7 1.547(3) . ?
C5 C6 1.568(3) . ?
C5 C11 1.534(3) . ?
C5 B1 1.657(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.538(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
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 C13 1.563(3) . ?
C12 C14 1.530(3) . ?
C12 C15 1.525(3) . ?
C13 C16 1.526(3) . ?
C13 C17 1.532(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O3 H3A 0.8701 . ?
O3 H3B 0.8703 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336278
