#------------------------------------------------------------------------------
#$Date: 2020-06-20 04:00:44 +0300 (Sat, 20 Jun 2020) $
#$Revision: 253282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558372.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_1558372
loop_
_publ_author_name
'Guo, Rui'
'Jiang, Jingxing'
'Hu, Chenyang'
'Liu, Liu Leo'
'Cui, Ping'
'Zhao, Meihua'
'Ke, Zhuofeng'
'Tung, Chen-Ho'
'Kong, Lingbing'
_publ_section_title
;
 BNN-1,3-dipoles: isolation and intramolecular cycloaddition with
 unactivated arenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02162H
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 B Br N'
_chemical_formula_sum            'C24 H26 B Br N'
_chemical_formula_weight         419.18
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-25 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.076(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4204(6)
_cell_length_b                   13.4075(4)
_cell_length_c                   13.5682(5)
_cell_measurement_reflns_used    5356
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      76.1910
_cell_measurement_theta_min      3.7450
_cell_volume                     2154.09(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -62.00   1.00    0.10    --  -48.45-155.00 175.00   26
  2  ω   -119.00 -74.00   1.00    0.10    --  -48.45-120.00 -28.00   45
  3  ω    -87.00 -35.00   1.00    0.10    --  -48.45 120.00  56.00   52
  4  ω     28.00  93.00   1.00    0.10    --   48.45-120.00 -28.00   65
  5  ω     57.00  82.00   1.00    0.10    --   48.45-155.00 175.00   25
  6  ω   -141.00-116.00   1.00    0.43    --  -86.25-120.00 -28.00   25
  7  ω     82.00 137.00   1.00    0.43    --  107.75-155.00 175.00   55
  8  ω     97.00 153.00   1.00    0.43    --  107.75 120.00  56.00   56
  9  ω     69.00 113.00   1.00    0.43    --  107.75-120.00 -28.00   44
 10  ω   -120.00 -26.00   1.00    0.10    --  -48.45 -77.00 -30.00   94
 11  ω     35.00 122.00   1.00    0.43    --  107.75 -57.00 -60.00   87
 12  ω     35.00 120.00   1.00    0.43    --  107.75 -37.00 -60.00   85
 13  ω     93.00 178.00   1.00    0.43    --  107.75  57.00-120.00   85
 14  ω     93.00 172.00   1.00    0.43    --  107.75  57.00 150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0299628000
_diffrn_orient_matrix_UB_12      -0.1107222000
_diffrn_orient_matrix_UB_13      -0.0016983000
_diffrn_orient_matrix_UB_21      -0.1258072000
_diffrn_orient_matrix_UB_22      -0.0278520000
_diffrn_orient_matrix_UB_23      -0.0497788000
_diffrn_orient_matrix_UB_31      -0.0140092000
_diffrn_orient_matrix_UB_32      0.0134804000
_diffrn_orient_matrix_UB_33      -0.1185935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11490
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         3.820
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0403
_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)+(0.0553P)²+1.7784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3104
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-2
_cod_database_code               1558372
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CBN
_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   0.621
_shelx_estimated_absorpt_t_min   0.505
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C20(H20), C9(H9), C18(H18), C4(H4)
3.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C22(H22a,H22b,H22c), C15(H15a,H15b,
 H15c), C24(H24a,H24b,H24c), C23(H23a,H23b,H23c)
;
_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 2.676
_oxdiff_exptl_absorpt_empirical_full_min 0.660
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.49763(3) 0.31920(2) 0.62183(3) 0.04048(15) Uani 1 1 d . . . . .
N1 N 0.5006(2) 0.51859(18) 0.54844(19) 0.0283(5) Uani 1 1 d D . . . .
C1 C 0.4985(2) 0.51670(19) 0.7365(2) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.7113(2) 0.5105(2) 0.8397(2) 0.0252(6) Uani 1 1 d . . . . .
C6 C 0.5998(2) 0.5411(2) 0.8317(2) 0.0256(5) Uani 1 1 d . . . . .
C2 C 0.3950(2) 0.5393(2) 0.7347(2) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.7675(2) 0.5710(2) 0.7977(2) 0.0284(6) Uani 1 1 d . . . . .
C12 C 0.7612(2) 0.4207(2) 0.8944(2) 0.0288(6) Uani 1 1 d . . . . .
C16 C 0.2868(2) 0.5036(2) 0.6391(2) 0.0269(6) Uani 1 1 d . . . . .
C21 C 0.2311(2) 0.5573(2) 0.5400(2) 0.0289(6) Uani 1 1 d . . . . .
C5 C 0.5971(2) 0.5906(2) 0.9206(2) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.6658 0.6077 0.9846 0.037 Uiso 1 1 calc R . . . .
C11 C 0.8652(2) 0.3930(2) 0.9038(2) 0.0304(6) Uani 1 1 d . . . . .
H11 H 0.8983 0.3318 0.9397 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3943(2) 0.5888(2) 0.8244(2) 0.0327(6) Uani 1 1 d . . . . .
H3 H 0.3246 0.6048 0.8228 0.039 Uiso 1 1 calc R . . . .
C20 C 0.1320(2) 0.5183(2) 0.4533(2) 0.0332(6) Uani 1 1 d . . . . .
H20 H 0.0949 0.5546 0.3853 0.040 Uiso 1 1 calc R . . . .
C17 C 0.2409(2) 0.4126(2) 0.6509(2) 0.0321(6) Uani 1 1 d . . . . .
C9 C 0.8722(2) 0.5401(2) 0.8097(2) 0.0319(6) Uani 1 1 d . . . . .
H9 H 0.9102 0.5810 0.7808 0.038 Uiso 1 1 calc R . . . .
C18 C 0.1421(3) 0.3773(2) 0.5631(3) 0.0362(7) Uani 1 1 d . . . . .
H18 H 0.1116 0.3159 0.5714 0.043 Uiso 1 1 calc R . . . .
C19 C 0.0863(2) 0.4292(2) 0.4629(2) 0.0345(7) Uani 1 1 d . . . . .
C10 C 0.9220(2) 0.4518(2) 0.8624(2) 0.0329(6) Uani 1 1 d . . . . .
C4 C 0.4954(3) 0.6149(2) 0.9162(2) 0.0351(7) Uani 1 1 d . . . . .
H4 H 0.4945 0.6498 0.9767 0.042 Uiso 1 1 calc R . . . .
C14 C 0.7041(3) 0.3545(2) 0.9431(3) 0.0384(7) Uani 1 1 d . . . . .
H14A H 0.6960 0.3910 1.0016 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.7501 0.2947 0.9754 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.6294 0.3350 0.8841 0.058 Uiso 1 1 calc GR . . . .
C13 C 0.7184(3) 0.6689(2) 0.7403(3) 0.0374(7) Uani 1 1 d . . . . .
H13A H 0.6487 0.6828 0.7443 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.7016 0.6648 0.6618 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.7730 0.7225 0.7774 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.2729(3) 0.6576(2) 0.5249(3) 0.0403(7) Uani 1 1 d . . . . .
H22A H 0.3325 0.6812 0.5970 0.060 Uiso 1 1 calc GR . . . .
H22B H 0.2102 0.7053 0.4959 0.060 Uiso 1 1 calc GR . . . .
H22C H 0.3031 0.6515 0.4720 0.060 Uiso 1 1 calc GR . . . .
C15 C 1.0345(3) 0.4186(3) 0.8749(3) 0.0433(8) Uani 1 1 d . . . . .
H15A H 1.0822 0.3952 0.9514 0.065 Uiso 1 1 calc GR . . . .
H15B H 1.0715 0.4747 0.8591 0.065 Uiso 1 1 calc GR . . . .
H15C H 1.0232 0.3642 0.8224 0.065 Uiso 1 1 calc GR . . . .
B1 B 0.4993(2) 0.4642(2) 0.6341(2) 0.0269(6) Uani 1 1 d . . . . .
C24 C -0.0210(3) 0.3879(3) 0.3690(3) 0.0452(8) Uani 1 1 d . . . . .
H24A H -0.0692 0.4430 0.3248 0.068 Uiso 1 1 calc GR . . . .
H24B H -0.0610 0.3484 0.4001 0.068 Uiso 1 1 calc GR . . . .
H24C H -0.0024 0.3455 0.3211 0.068 Uiso 1 1 calc GR . . . .
C23 C 0.2977(3) 0.3527(3) 0.7578(3) 0.0461(8) Uani 1 1 d . . . . .
H23A H 0.3749 0.3363 0.7736 0.069 Uiso 1 1 calc GR . . . .
H23B H 0.2552 0.2910 0.7494 0.069 Uiso 1 1 calc GR . . . .
H23C H 0.2996 0.3920 0.8196 0.069 Uiso 1 1 calc GR . . . .
H1 H 0.501(3) 0.5852(14) 0.554(3) 0.055 Uiso 1 1 d DR . . . .
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'
Br Br -0.6763 1.2805 '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'
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
N1 N1 H1 115(3) 3_666 . ?
B1 N1 N1 127.2(3) . 3_666 ?
B1 N1 H1 118(2) . . ?
C6 C1 C2 119.1(2) . . ?
C6 C1 B1 120.9(2) . . ?
C2 C1 B1 120.0(2) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 C12 119.8(3) . . ?
C12 C7 C6 118.8(2) . . ?
C1 C6 C7 120.2(2) . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 119.8(2) . . ?
C1 C2 C16 119.5(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 C16 120.5(2) . . ?
C7 C8 C9 119.0(3) . . ?
C7 C8 C13 121.8(3) . . ?
C9 C8 C13 119.2(3) . . ?
C7 C12 C14 121.3(3) . . ?
C11 C12 C7 119.0(3) . . ?
C11 C12 C14 119.7(3) . . ?
C21 C16 C2 122.1(3) . . ?
C21 C16 C17 119.5(3) . . ?
C17 C16 C2 118.4(2) . . ?
C16 C21 C20 119.0(3) . . ?
C16 C21 C22 121.9(3) . . ?
C20 C21 C22 119.1(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C21 C20 H20 118.8 . . ?
C19 C20 C21 122.3(3) . . ?
C19 C20 H20 118.8 . . ?
C16 C17 C23 121.2(3) . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 C23 119.4(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.9(3) . . ?
C10 C9 H9 119.1 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.9(3) . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 117.9(3) . . ?
C20 C19 C24 121.9(3) . . ?
C18 C19 C24 120.2(3) . . ?
C11 C10 C15 120.0(3) . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 C15 121.7(3) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
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 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 B1 Br1 117.3(2) . . ?
N1 B1 C1 121.3(3) . . ?
C1 B1 Br1 121.4(2) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Br1 B1 1.951(3) . ?
N1 N1 1.399(4) 3_666 ?
N1 B1 1.379(4) . ?
N1 H1 0.895(19) . ?
C1 C6 1.404(4) . ?
C1 C2 1.410(4) . ?
C1 B1 1.562(4) . ?
C7 C6 1.505(4) . ?
C7 C8 1.399(4) . ?
C7 C12 1.407(4) . ?
C6 C5 1.392(4) . ?
C2 C16 1.499(4) . ?
C2 C3 1.390(4) . ?
C8 C9 1.400(4) . ?
C8 C13 1.509(4) . ?
C12 C11 1.391(4) . ?
C12 C14 1.512(4) . ?
C16 C21 1.393(4) . ?
C16 C17 1.409(4) . ?
C21 C20 1.398(4) . ?
C21 C22 1.508(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.378(5) . ?
C17 C18 1.384(4) . ?
C17 C23 1.512(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(4) . ?
C19 C24 1.508(4) . ?
C10 C15 1.506(4) . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
