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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/51/4035121.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_4035121
loop_
_publ_author_name
'Andresini, Michael'
'De Angelis, Sonia'
'Uricchio, Antonella'
'Visaggio, Angelica'
'Romanazzi, Giuseppe'
'Ciriaco, Fulvio'
'Corriero, Nicola'
'Degennaro, Leonardo'
'Luisi, Renzo'
_publ_section_title
;
 Azetidine-Borane Complexes: Synthesis, Reactivity, and Stereoselective
 Functionalization.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10221
_journal_page_last               10230
_journal_paper_doi               10.1021/acs.joc.8b01441
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C11 H18 B N'
_chemical_formula_weight         175.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.30(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.820(5)
_cell_length_b                   6.017(1)
_cell_length_c                   14.764(5)
_cell_measurement_reflns_used    130
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2
_cell_volume                     1103.6(6)
_computing_cell_refinement
'DIRAX (Duisenberg,1992; Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'EVAL (Nonius, 2002; Duisenberg et al., 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11147
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         3.674
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.4793
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1454P)²+0.0610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2311
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1619
_reflns_number_total             2521
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01441_si_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1103.6(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035121
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.19213(12) 0.2199(2) 0.90936(11) 0.0493(4) Uani 1 1 d . U
C1 C 0.28353(15) 0.0938(3) 1.08068(13) 0.0516(5) Uani 1 1 d . U
C2 C 0.22754(14) 0.2709(3) 1.01516(13) 0.0493(5) Uani 1 1 d . U
H2 H 0.2734 0.4034 1.0242 0.059 Uiso 1 1 calc R U
C3 C 0.39633(16) 0.0873(4) 1.11216(15) 0.0647(6) Uani 1 1 d . U
C4 C 0.22354(18) -0.0643(3) 1.11497(14) 0.0636(6) Uani 1 1 d . U
H4 H 0.1489 -0.0607 1.0941 0.076 Uiso 1 1 calc R U
C5 C 0.11170(16) 0.3435(4) 1.01164(16) 0.0625(6) Uani 1 1 d . U
H5A H 0.0686 0.2299 1.0316 0.075 Uiso 1 1 calc R U
H5B H 0.1066 0.4841 1.0424 0.075 Uiso 1 1 calc R U
C6 C 0.09398(17) 0.3610(3) 0.90612(16) 0.0627(6) Uani 1 1 d . U
H6A H 0.0274 0.2931 0.8716 0.075 Uiso 1 1 calc R U
H6B H 0.1003 0.5114 0.8845 0.075 Uiso 1 1 calc R U
C7 C 0.2647(2) 0.3085(4) 0.85355(18) 0.0776(7) Uani 1 1 d . U
H7A H 0.3299 0.2228 0.8663 0.116 Uiso 1 1 calc R U
H7B H 0.2815 0.4609 0.8701 0.116 Uiso 1 1 calc R U
H7C H 0.2296 0.2988 0.7882 0.116 Uiso 1 1 calc R U
C8 C 0.4412(2) -0.0817(5) 1.17636(18) 0.0832(8) Uani 1 1 d . U
H8 H 0.5156 -0.0904 1.1977 0.100 Uiso 1 1 calc R U
C9 C 0.2699(2) -0.2254(4) 1.17833(17) 0.0789(7) Uani 1 1 d . U
H9 H 0.2275 -0.3274 1.2003 0.095 Uiso 1 1 calc R U
B1 B 0.1605(2) -0.0327(4) 0.88115(18) 0.0608(6) Uani 1 1 d . U
H3B H 0.237(2) -0.130(4) 0.8987(18) 0.091 Uiso 1 1 d . U
H2B H 0.103(2) -0.091(4) 0.9195(19) 0.091 Uiso 1 1 d . U
H1B H 0.124(2) -0.029(4) 0.8055(19) 0.091 Uiso 1 1 d . U
C11 C 0.3790(3) -0.2329(5) 1.20827(18) 0.0882(8) Uani 1 1 d . U
H11 H 0.4116 -0.3415 1.2507 0.106 Uiso 1 1 calc R U
C12 C 0.46841(19) 0.2508(5) 1.0811(2) 0.0922(9) Uani 1 1 d . U
H12A H 0.4424 0.3988 1.0861 0.138 Uiso 1 1 calc R U
H12B H 0.4689 0.2214 1.0173 0.138 Uiso 1 1 calc R U
H12C H 0.5402 0.2370 1.1200 0.138 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 114.34(16)
C7 N1 C2 114.93(16)
C6 N1 C2 87.42(13)
C7 N1 B1 110.44(16)
C6 N1 B1 111.72(16)
C2 N1 B1 116.32(15)
C4 C1 C3 118.40(19)
C4 C1 C2 120.02(17)
C3 C1 C2 121.52(18)
C1 C2 C5 121.96(17)
C1 C2 N1 119.06(13)
C5 C2 N1 88.98(13)
C1 C3 C8 117.2(2)
C1 C3 C12 122.9(2)
C8 C3 C12 119.9(2)
C9 C4 C1 122.9(2)
C6 C5 C2 87.30(15)
N1 C6 C5 90.92(14)
C11 C8 C3 122.4(2)
C11 C9 C4 118.8(3)
C9 C11 C8 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.486(3)
N1 C6 1.509(2)
N1 C2 1.546(2)
N1 B1 1.601(3)
C1 C4 1.395(3)
C1 C3 1.406(3)
C1 C2 1.498(2)
C2 C5 1.537(3)
C3 C8 1.412(4)
C3 C12 1.497(4)
C4 C9 1.376(3)
C5 C6 1.522(3)
C8 C11 1.367(4)
C9 C11 1.359(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328928
