#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:13:58 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193818 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/16/7041649.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_7041649
loop_
_publ_author_name
'Chernichenko, K.'
'Kótai, B'
'Nieger, M.'
'Heikkinen, S.'
'Pápai, I'
'Repo, T.'
_publ_section_title
;
 Replacing C6F5 groups with Cl and H atoms in frustrated Lewis pairs: H2
 additions and catalytic hydrogenations.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2263
_journal_page_last               2269
_journal_paper_doi               10.1039/c6dt04649e
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C15 H24 B Cl2 N'
_chemical_formula_sum            'C15 H24 B Cl2 N'
_chemical_formula_weight         300.06
_chemical_name_systematic
;
dichloro(2-(2,2,6,6-tetramethylpiperidin-1-ium-1-yl)phenyl)hydroborate
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-11-26 deposited with the CCDC.
2017-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1847(5)
_cell_length_b                   11.3284(5)
_cell_length_c                   12.5977(6)
_cell_measurement_reflns_used    97
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     1596.19(13)
_computing_cell_refinement       EVALCCD
_computing_data_collection       Collect
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg,'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16342
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0225
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0319P)²+0.6431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                1851
_reflns_number_total             1921
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt04649e2.cif
_cod_data_source_block           les095_c_compound_9c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7041648--7041652.cif.
;
_cod_database_code               7041649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
Cl1 Cl 0.36309(2) 0.17603(2) 0.38679(4) 0.02378(9) Uani 1 1 d .
B1 B 0.5000 0.24141(17) 0.32246(15) 0.0155(4) Uani 1 2 d S
H1 H 0.5000 0.3395(18) 0.3473(17) 0.019 Uiso 1 2 d S
C2 C 0.5000 0.21369(15) 0.19715(13) 0.0149(3) Uani 1 2 d S
C3 C 0.5000 0.09575(16) 0.16246(14) 0.0197(4) Uani 1 2 d S
H3 H 0.5000 0.0347 0.2141 0.024 Uiso 1 2 calc SR
C4 C 0.5000 0.06499(18) 0.05639(16) 0.0262(4) Uani 1 2 d S
H4 H 0.5000 -0.0158 0.0361 0.031 Uiso 1 2 calc SR
C5 C 0.5000 0.15262(19) -0.02009(16) 0.0314(5) Uani 1 2 d S
H5 H 0.5000 0.1318 -0.0931 0.038 Uiso 1 2 calc SR
C6 C 0.5000 0.27117(18) 0.00938(14) 0.0263(4) Uani 1 2 d S
H6 H 0.5000 0.3316 -0.0429 0.032 Uiso 1 2 calc SR
C7 C 0.5000 0.29958(17) 0.11722(15) 0.0167(4) Uani 1 2 d S
N8 N 0.5000 0.42498(12) 0.15211(11) 0.0138(3) Uani 1 2 d S
H8 H 0.5000 0.4166(19) 0.2199(19) 0.017 Uiso 1 2 d S
C9 C 0.37926(9) 0.49260(14) 0.13480(15) 0.0197(2) Uani 1 1 d .
C10 C 0.38902(14) 0.60645(12) 0.19914(12) 0.0285(3) Uani 1 1 d .
H10A H 0.3173 0.6553 0.1853 0.034 Uiso 1 1 calc R
H10B H 0.3892 0.5862 0.2756 0.034 Uiso 1 1 calc R
C11 C 0.5000 0.67936(17) 0.17462(19) 0.0311(6) Uani 1 2 d S
H11A H 0.5000 0.7025 0.0988 0.037 Uiso 1 2 calc SR
H11B H 0.5000 0.7521 0.2182 0.037 Uiso 1 2 calc SR
C12 C 0.35041(12) 0.51722(13) 0.01852(11) 0.0260(3) Uani 1 1 d .
H12A H 0.3450 0.4424 -0.0202 0.039 Uiso 1 1 calc R
H12B H 0.4138 0.5660 -0.0125 0.039 Uiso 1 1 calc R
H12C H 0.2739 0.5591 0.0136 0.039 Uiso 1 1 calc R
C13 C 0.28117(12) 0.41399(13) 0.18175(13) 0.0307(3) Uani 1 1 d .
H13A H 0.2755 0.3408 0.1405 0.046 Uiso 1 1 calc R
H13B H 0.2045 0.4557 0.1791 0.046 Uiso 1 1 calc R
H13C H 0.3008 0.3951 0.2556 0.046 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C2 B1 Cl1 110.19(8) . 4_655
C2 B1 Cl1 110.19(8) . .
Cl1 B1 Cl1 108.72(9) 4_655 .
C2 B1 H1 117.0(10) . .
Cl1 B1 H1 105.2(6) 4_655 .
Cl1 B1 H1 105.2(6) . .
C7 C2 C3 115.90(16) . .
C7 C2 B1 124.73(15) . .
C3 C2 B1 119.36(15) . .
C4 C3 C2 122.73(17) . .
C4 C3 H3 118.6 . .
C2 C3 H3 118.6 . .
C3 C4 C5 119.53(18) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C4 C5 C6 120.40(18) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C5 C6 C7 118.78(18) . .
C5 C6 H6 120.6 . .
C7 C6 H6 120.6 . .
C6 C7 C2 122.66(18) . .
C6 C7 N8 120.52(16) . .
C2 C7 N8 116.82(15) . .
C7 N8 C9 115.19(8) . 4_655
C7 N8 C9 115.19(8) . .
C9 N8 C9 118.94(14) 4_655 .
C7 N8 H8 100.8(14) . .
C9 N8 H8 101.1(7) 4_655 .
C9 N8 H8 101.1(7) . .
C12 C9 C10 111.74(13) . .
C12 C9 C13 109.00(12) . .
C10 C9 C13 109.71(13) . .
C12 C9 N8 113.89(13) . .
C10 C9 N8 106.09(11) . .
C13 C9 N8 106.21(12) . .
C11 C10 C9 114.13(13) . .
C11 C10 H10A 108.7 . .
C9 C10 H10A 108.7 . .
C11 C10 H10B 108.7 . .
C9 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
C10 C11 C10 109.21(15) 4_655 .
C10 C11 H11A 109.8 4_655 .
C10 C11 H11A 109.8 . .
C10 C11 H11B 109.8 4_655 .
C10 C11 H11B 109.8 . .
H11A C11 H11B 108.3 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 B1 1.8842(11) .
B1 C2 1.610(2) .
B1 Cl1 1.8842(11) 4_655
B1 H1 1.15(2) .
C2 C7 1.400(2) .
C2 C3 1.406(2) .
C3 C4 1.381(3) .
C3 H3 0.9500 .
C4 C5 1.383(3) .
C4 H4 0.9500 .
C5 C6 1.393(3) .
C5 H5 0.9500 .
C6 C7 1.396(3) .
C6 H6 0.9500 .
C7 N8 1.487(2) .
N8 C9 1.5679(13) 4_655
N8 C9 1.5679(13) .
N8 H8 0.86(2) .
C9 C12 1.526(2) .
C9 C10 1.527(2) .
C9 C13 1.5318(19) .
C10 C11 1.5226(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C10 1.5226(19) 4_655
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N8 H8 H1 0.86(2) 1.83(3) 2.64(2) 158(2)
B1 H1 H8 1.15(2) 1.83(3) 2.37(2) 102.8(15)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
Cl1 B1 C2 C7 -120.02(8) 4_655 .
Cl1 B1 C2 C7 120.02(8) . .
Cl1 B1 C2 C3 59.98(8) 4_655 .
Cl1 B1 C2 C3 -59.98(8) . .
C7 C2 C3 C4 0.0 . .
B1 C2 C3 C4 180.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C7 0.0 . .
C5 C6 C7 C2 0.0 . .
C5 C6 C7 N8 180.0 . .
C3 C2 C7 C6 0.0 . .
B1 C2 C7 C6 180.0 . .
C3 C2 C7 N8 180.0 . .
B1 C2 C7 N8 0.0 . .
C6 C7 N8 C9 -72.15(11) . 4_655
C2 C7 N8 C9 107.85(11) . 4_655
C6 C7 N8 C9 72.15(11) . .
C2 C7 N8 C9 -107.85(11) . .
C7 N8 C9 C12 -70.10(16) . .
C9 N8 C9 C12 72.8(2) 4_655 .
C7 N8 C9 C10 166.57(13) . .
C9 N8 C9 C10 -50.5(2) 4_655 .
C7 N8 C9 C13 49.87(18) . .
C9 N8 C9 C13 -167.24(10) 4_655 .
C12 C9 C10 C11 -71.22(15) . .
C13 C9 C10 C11 167.78(13) . .
N8 C9 C10 C11 53.45(17) . .
C9 C10 C11 C10 -60.3(2) . 4_655
