#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:44:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180153 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/49/7104967.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_7104967
loop_
_publ_author_name
'Liao, Wenyan'
'Chen, Yunfeng'
'Liu, Yuxiu'
'Duan, Haifeng'
'Petersen, Jeffrey L'
'Shi, Xiaodong'
_publ_section_title
;
 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and
 aldehyde reductive amination in organic solvents or in water.
;
_journal_issue                   42
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6436
_journal_page_last               6438
_journal_paper_doi               10.1039/b915361f
_journal_year                    2009
_chemical_formula_sum            'C7 H10 B N3'
_chemical_formula_weight         146.99
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.839(2)
_cell_angle_beta                 103.1050(10)
_cell_angle_gamma                94.8700(10)
_cell_formula_units_Z            4
_cell_length_a                   8.1841(7)
_cell_length_b                   8.4683(7)
_cell_length_c                   12.0614(10)
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.73
_cell_volume                     809.17(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0736
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5506
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1140P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.1984
_reflns_number_gt                2661
_reflns_number_total             3518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b915361f.txt
_cod_data_source_block           ms77alt
_cod_original_sg_symbol_H-M      P_-1
_cod_database_code               7104967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32245(16) 0.27772(15) 1.00618(10) 0.0442(3) Uani 1 1 d . . .
N2 N 0.46696(17) 0.21828(15) 1.01318(10) 0.0468(3) Uani 1 1 d . . .
N3 N 0.52978(16) 0.26961(15) 0.92789(10) 0.0444(3) Uani 1 1 d . . .
N4 N 1.06467(15) 0.77902(15) 0.42156(10) 0.0433(3) Uani 1 1 d . . .
N5 N 0.99724(16) 0.72277(15) 0.50217(10) 0.0461(3) Uani 1 1 d . . .
N6 N 0.84671(16) 0.77677(15) 0.48971(10) 0.0440(3) Uani 1 1 d . . .
C1 C 0.29027(18) 0.36956(16) 0.91436(12) 0.0416(4) Uani 1 1 d . . .
C2 C 0.42566(19) 0.36517(16) 0.86306(11) 0.0416(4) Uani 1 1 d . . .
C3 C 0.4343(2) 0.44607(19) 0.76576(13) 0.0553(4) Uani 1 1 d . . .
H3 H 0.5257 0.4438 0.7320 0.066 Uiso 1 1 calc R . .
C4 C 0.2997(3) 0.5289(2) 0.72339(15) 0.0647(5) Uani 1 1 d . . .
H4 H 0.2997 0.5845 0.6588 0.078 Uiso 1 1 calc R . .
C5 C 0.1612(3) 0.5324(2) 0.77452(16) 0.0643(5) Uani 1 1 d . . .
H5 H 0.0726 0.5900 0.7424 0.077 Uiso 1 1 calc R . .
C6 C 0.1529(2) 0.45386(19) 0.86981(14) 0.0551(4) Uani 1 1 d . . .
H6 H 0.0612 0.4563 0.9032 0.066 Uiso 1 1 calc R . .
C7 C 0.6896(2) 0.2196(2) 0.91184(15) 0.0623(5) Uani 1 1 d . . .
H7A H 0.7809 0.2787 0.9662 0.093 Uiso 1 1 calc R . .
H7B H 0.7004 0.2389 0.8359 0.093 Uiso 1 1 calc R . .
H7C H 0.6925 0.1083 0.9228 0.093 Uiso 1 1 calc R . .
C8 C 0.95679(19) 0.87128(17) 0.35515(11) 0.0408(4) Uani 1 1 d . . .
C9 C 0.81462(18) 0.87077(17) 0.39954(11) 0.0416(4) Uani 1 1 d . . .
C10 C 0.6768(2) 0.95364(19) 0.35254(14) 0.0539(4) Uani 1 1 d . . .
H10 H 0.5817 0.9533 0.3826 0.065 Uiso 1 1 calc R . .
C11 C 0.6919(3) 1.0352(2) 0.25930(16) 0.0638(5) Uani 1 1 d . . .
H11 H 0.6042 1.0926 0.2252 0.077 Uiso 1 1 calc R . .
C12 C 0.8354(3) 1.0351(2) 0.21344(14) 0.0630(5) Uani 1 1 d . . .
H12 H 0.8388 1.0917 0.1497 0.076 Uiso 1 1 calc R . .
C13 C 0.9701(2) 0.9548(2) 0.25904(13) 0.0553(4) Uani 1 1 d . . .
H13 H 1.0647 0.9553 0.2284 0.066 Uiso 1 1 calc R . .
C14 C 0.7379(2) 0.7323(2) 0.56594(15) 0.0631(5) Uani 1 1 d . . .
H14A H 0.7545 0.8126 0.6276 0.095 Uiso 0.58(2) 1 calc PR A 1
H14B H 0.7653 0.6326 0.5961 0.095 Uiso 0.58(2) 1 calc PR A 1
H14C H 0.6222 0.7226 0.5244 0.095 Uiso 0.58(2) 1 calc PR A 1
H14D H 0.6696 0.8168 0.5745 0.095 Uiso 0.42(2) 1 d PR A 2
H14E H 0.8060 0.7135 0.6391 0.095 Uiso 0.42(2) 1 d PR A 2
H14F H 0.6665 0.6375 0.5343 0.095 Uiso 0.42(2) 1 d PR A 2
B1 B 0.2086(3) 0.2419(3) 1.09348(18) 0.0626(5) Uani 1 1 d . . .
H1A H 0.2689 0.1854 1.1543 0.094 Uiso 1 1 calc R . .
H1B H 0.1069 0.1785 1.0549 0.094 Uiso 1 1 calc R . .
H1C H 0.1809 0.3402 1.1243 0.094 Uiso 1 1 calc R . .
B2 B 1.2438(3) 0.7397(3) 0.40635(17) 0.0603(5) Uani 1 1 d . . .
H2A H 1.2308 0.6723 0.3379 0.091 Uiso 0.72(3) 1 calc PR B 1
H2B H 1.2988 0.6864 0.4708 0.091 Uiso 0.72(3) 1 calc PR B 1
H2C H 1.3107 0.8366 0.4010 0.091 Uiso 0.72(3) 1 calc PR B 1
H2D H 1.2389 0.6295 0.3817 0.091 Uiso 0.28(3) 1 d PR B 2
H2E H 1.3248 0.7616 0.4778 0.091 Uiso 0.28(3) 1 d PR B 2
H2F H 1.2765 0.8042 0.3503 0.091 Uiso 0.28(3) 1 d PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 109.94(12) . . ?
N2 N1 B1 122.28(14) . . ?
C1 N1 B1 127.78(14) . . ?
N1 N2 N3 107.38(12) . . ?
N2 N3 C2 111.51(13) . . ?
N2 N3 C7 120.03(13) . . ?
C2 N3 C7 128.45(14) . . ?
N5 N4 C8 110.27(13) . . ?
N5 N4 B2 122.72(14) . . ?
C8 N4 B2 127.00(14) . . ?
N4 N5 N6 107.16(12) . . ?
N5 N6 C9 111.32(12) . . ?
N5 N6 C14 120.51(14) . . ?
C9 N6 C14 128.16(14) . . ?
N1 C1 C2 106.87(13) . . ?
N1 C1 C6 131.75(15) . . ?
C2 C1 C6 121.37(15) . . ?
N3 C2 C1 104.30(13) . . ?
N3 C2 C3 133.41(16) . . ?
C1 C2 C3 122.29(15) . . ?
C4 C3 C2 115.79(18) . . ?
C3 C4 C5 122.11(18) . . ?
C6 C5 C4 122.14(16) . . ?
C5 C6 C1 116.30(17) . . ?
N4 C8 C9 106.67(13) . . ?
N4 C8 C13 131.86(15) . . ?
C9 C8 C13 121.46(15) . . ?
N6 C9 C8 104.57(13) . . ?
N6 C9 C10 133.00(15) . . ?
C8 C9 C10 122.43(15) . . ?
C11 C10 C9 115.49(17) . . ?
C10 C11 C12 122.27(17) . . ?
C13 C12 C11 122.46(17) . . ?
C12 C13 C8 115.89(17) . . ?
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
N1 N2 1.3112(18) . ?
N1 C1 1.3743(18) . ?
N1 B1 1.580(2) . ?
N2 N3 1.3258(18) . ?
N3 C2 1.3675(19) . ?
N3 C7 1.459(2) . ?
N4 N5 1.3120(18) . ?
N4 C8 1.3747(19) . ?
N4 B2 1.578(2) . ?
N5 N6 1.3297(18) . ?
N6 C9 1.3700(19) . ?
N6 C14 1.459(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.400(2) . ?
C3 C4 1.371(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.368(3) . ?
C8 C9 1.387(2) . ?
C8 C13 1.408(2) . ?
C9 C10 1.404(2) . ?
C10 C11 1.372(3) . ?
C11 C12 1.408(3) . ?
C12 C13 1.367(3) . ?
