#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:47:42 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/94/7039429.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_7039429
loop_
_publ_author_name
'Antiñolo, Antonio'
'Carrillo-Hermosilla, Fernando'
'Fernández-Galán, Rafael'
'Martínez-Ferrer, Jaime'
'Alonso-Moreno, Carlos'
'Bravo, Iván'
'Moreno-Blázquez, Sonia'
'Salgado, Manuel'
'Villaseñor, Elena'
'Albaladejo, José'
_publ_section_title
;
 Tris(pentafluorophenyl)borane as an efficient catalyst in the guanylation
 reaction of amines.
;
_journal_issue                   26
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10717
_journal_page_last               10729
_journal_paper_doi               10.1039/c6dt01237j
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C13 H21 N3'
_chemical_formula_weight         219.33
_chemical_name_common            3a
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-02-02 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.869(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1014(5)
_cell_length_b                   11.3796(5)
_cell_length_c                   8.7040(4)
_cell_measurement_reflns_used    6062
_cell_measurement_temperature    210.(2)
_cell_measurement_theta_max      26.3651
_cell_measurement_theta_min      2.3465
_cell_volume                     1329.34(10)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      210.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  BrukerKappaApex2
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13122
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0350
_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)+(0.0654P)²+0.4029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2085
_reflns_number_total             2435
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt01237j2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7039427--7039429.cif.'
_cod_database_code               7039429
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.24302(9) 0.96979(11) 0.32893(14) 0.0287(3) Uani d . 1
C C2 0.17848(10) 0.99338(13) 0.41829(16) 0.0354(3) Uani d . 1
H H2 0.1496 0.9308 0.4585 0.042 Uiso calc R 1
C C3 0.15634(12) 1.10802(14) 0.44871(18) 0.0444(4) Uani d . 1
H H3 0.1125 1.1224 0.509 0.053 Uiso calc R 1
C C4 0.19801(13) 1.20093(14) 0.39125(19) 0.0473(4) Uani d . 1
H H4 0.1828 1.2786 0.4119 0.057 Uiso calc R 1
C C5 0.26233(12) 1.17884(13) 0.30296(19) 0.0439(4) Uani d . 1
H H5 0.2908 1.242 0.263 0.053 Uiso calc R 1
C C6 0.28541(11) 1.06470(13) 0.27259(17) 0.0367(3) Uani d . 1
H H6 0.3301 1.0511 0.2135 0.044 Uiso calc R 1
C C7 0.27301(9) 0.80939(11) 0.17518(15) 0.0285(3) Uani d . 1
C C8 0.40747(10) 0.66606(12) 0.30776(17) 0.0343(3) Uani d . 1
H H8 0.3857 0.6628 0.4055 0.041 Uiso calc R 1
C C9 0.43070(14) 0.54219(15) 0.2654(2) 0.0589(5) Uani d . 1
H H9A 0.3731 0.4923 0.2533 0.088 Uiso calc R 1
H H9B 0.4869 0.5116 0.3509 0.088 Uiso calc R 1
H H9C 0.447 0.5435 0.165 0.088 Uiso calc R 1
C C10 0.49748(12) 0.74512(16) 0.3412(2) 0.0561(5) Uani d . 1
H H10A 0.52 0.7483 0.2466 0.084 Uiso calc R 1
H H10B 0.5504 0.7144 0.4319 0.084 Uiso calc R 1
H H10C 0.4799 0.8236 0.3666 0.084 Uiso calc R 1
C C11 0.12822(10) 0.91080(12) -0.02321(16) 0.0352(3) Uani d . 1
H H11 0.1305 0.9768 0.052 0.042 Uiso calc R 1
C C12 0.11070(13) 0.96032(14) -0.19080(19) 0.0479(4) Uani d . 1
H H12A 0.1644 1.0137 -0.1903 0.072 Uiso calc R 1
H H12B 0.0479 1.0024 -0.2238 0.072 Uiso calc R 1
H H12C 0.1086 0.8966 -0.2658 0.072 Uiso calc R 1
C C13 0.04596(12) 0.82785(16) -0.0164(2) 0.0538(5) Uani d . 1
H H13A 0.044 0.7616 -0.0874 0.081 Uiso calc R 1
H H13B -0.0174 0.8688 -0.0508 0.081 Uiso calc R 1
H H13C 0.0585 0.7999 0.0933 0.081 Uiso calc R 1
N N1 0.27058(8) 0.85241(9) 0.31295(13) 0.0312(3) Uani d . 1
N N2 0.32501(9) 0.70931(10) 0.17345(15) 0.0350(3) Uani d . 1
N N3 0.22596(8) 0.85306(11) 0.02397(14) 0.0341(3) Uani d . 1
H H3N 0.2336(12) 0.8080(15) -0.051(2) 0.040(4) Uiso d . 1
H H2N 0.3224(11) 0.6823(14) 0.081(2) 0.038(4) Uiso d . 1
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'
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
C6 C1 C2 118.11(12)
C6 C1 N1 122.57(12)
C2 C1 N1 119.00(12)
C3 C2 C1 120.82(14)
C3 C2 H2 119.6
C1 C2 H2 119.6
C4 C3 C2 120.50(14)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.30(14)
C3 C4 H4 120.4
C5 C4 H4 120.4
C4 C5 C6 120.71(15)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 120.56(14)
C5 C6 H6 119.7
C1 C6 H6 119.7
N1 C7 N2 119.43(12)
N1 C7 N3 127.16(12)
N2 C7 N3 113.39(11)
N2 C8 C10 111.70(12)
N2 C8 C9 107.29(12)
C10 C8 C9 111.65(13)
N2 C8 H8 108.7
C10 C8 H8 108.7
C9 C8 H8 108.7
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C11 C12 107.35(12)
N3 C11 C13 112.08(12)
C12 C11 C13 111.76(13)
N3 C11 H11 108.5
C12 C11 H11 108.5
C13 C11 H11 108.5
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C7 N1 C1 122.11(11)
C7 N2 C8 125.10(12)
C7 N2 H2N 116.5(11)
C8 N2 H2N 115.4(11)
C7 N3 C11 124.52(11)
C7 N3 H3N 112.0(11)
C11 N3 H3N 112.2(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3944(19)
C1 C2 1.3928(19)
C1 N1 1.4099(16)
C2 C3 1.386(2)
C2 H2 0.94
C3 C4 1.376(2)
C3 H3 0.94
C4 C5 1.380(2)
C4 H4 0.94
C5 C6 1.384(2)
C5 H5 0.94
C6 H6 0.94
C7 N1 1.3054(17)
C7 N2 1.3571(17)
C7 N3 1.3724(17)
C8 N2 1.4583(18)
C8 C10 1.510(2)
C8 C9 1.518(2)
C8 H8 0.99
C9 H9A 0.97
C9 H9B 0.97
C9 H9C 0.97
C10 H10A 0.97
C10 H10B 0.97
C10 H10C 0.97
C11 N3 1.4673(17)
C11 C12 1.512(2)
C11 C13 1.511(2)
C11 H11 0.99
C12 H12A 0.97
C12 H12B 0.97
C12 H12C 0.97
C13 H13A 0.97
C13 H13B 0.97
C13 H13C 0.97
N2 H2N 0.853(17)
N3 H3N 0.862(18)
