#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:40:53 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/57/7235783.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_7235783
loop_
_publ_author_name
'Rekken, B. D.'
'Carre-Burritt, A. E.'
'Scott, B. L.'
'Davis, B. L.'
_publ_section_title
;
 N-substituted amine-borane ionic liquids as fluid phase, hydrogen storage
 materials
;
_journal_issue                   39
_journal_name_full               'J. Mater. Chem. A'
_journal_page_first              16507
_journal_paper_doi               10.1039/C4TA03853C
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C7 H15 Cl2 N3'
_chemical_formula_weight         212.12
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.7620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2973(11)
_cell_length_b                   13.2211(14)
_cell_length_c                   8.8908(9)
_cell_measurement_temperature    140(1)
_cell_volume                     1116.1(2)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12717
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.9480
_exptl_absorpt_correction_T_min  0.8815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0283
_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)+(0.0266P)²+0.4129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                2321
_reflns_number_total             2707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ta03853c2.cif
_cod_data_source_block           eimetnh3_2cl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235783
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.16806(3) 0.13082(2) 0.92560(4) 0.01769(9) Uani 1 1 d .
Cl2 Cl 0.25448(3) 0.64394(2) 0.06718(4) 0.01880(9) Uani 1 1 d .
N1 N 0.37359(12) 0.13409(8) 0.62383(14) 0.0154(2) Uani 1 1 d .
N2 N 0.18592(11) 0.09873(8) 0.41379(13) 0.0147(2) Uani 1 1 d .
N3 N -0.08122(12) 0.22754(9) 0.23791(14) 0.0185(2) Uani 1 1 d .
H3A H -0.1308 0.2113 0.2972 0.028 Uiso 1 1 calc R
H3B H -0.1339 0.2653 0.1534 0.028 Uiso 1 1 calc R
H3C H -0.0050 0.2622 0.2992 0.028 Uiso 1 1 calc R
C1 C 0.57293(17) 0.06979(14) 0.8616(2) 0.0360(4) Uani 1 1 d .
H1A H 0.5245 0.0061 0.8431 0.054 Uiso 1 1 calc R
H1B H 0.6233 0.0798 0.9766 0.054 Uiso 1 1 calc R
H1C H 0.6381 0.0700 0.8082 0.054 Uiso 1 1 calc R
C2 C 0.46722(15) 0.15417(11) 0.79359(17) 0.0216(3) Uani 1 1 d .
H2A H 0.4115 0.1612 0.8595 0.026 Uiso 1 1 calc R
H2B H 0.5168 0.2173 0.7992 0.026 Uiso 1 1 calc R
C3 C 0.23721(14) 0.11371(10) 0.57375(16) 0.0153(3) Uani 1 1 d .
H3 H 0.1860 0.1105 0.6398 0.018 Uiso 1 1 calc R
C4 C 0.41128(15) 0.13079(10) 0.49114(17) 0.0192(3) Uani 1 1 d .
H4 H 0.5009 0.1414 0.4921 0.023 Uiso 1 1 calc R
C5 C 0.29355(15) 0.10920(10) 0.35928(17) 0.0194(3) Uani 1 1 d .
H5 H 0.2865 0.1027 0.2523 0.023 Uiso 1 1 calc R
C6 C 0.04326(14) 0.06335(10) 0.31577(16) 0.0192(3) Uani 1 1 d .
H6A H -0.0082 0.0553 0.3862 0.023 Uiso 1 1 calc R
H6B H 0.0492 -0.0026 0.2709 0.023 Uiso 1 1 calc R
C7 C -0.03793(14) 0.13384(11) 0.17775(16) 0.0195(3) Uani 1 1 d .
H7A H 0.0201 0.1516 0.1180 0.023 Uiso 1 1 calc R
H7B H -0.1211 0.0993 0.1032 0.023 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01912(17) 0.01953(17) 0.01529(16) -0.00002(12) 0.00762(13) 0.00106(12)
Cl2 0.01732(17) 0.01863(17) 0.02217(17) 0.00129(12) 0.00954(13) 0.00129(12)
N1 0.0141(5) 0.0143(5) 0.0174(6) -0.0011(4) 0.0058(4) 0.0004(4)
N2 0.0149(5) 0.0136(5) 0.0153(5) 0.0006(4) 0.0054(4) 0.0003(4)
N3 0.0164(6) 0.0204(6) 0.0193(6) 0.0025(5) 0.0076(5) -0.0012(5)
C1 0.0260(8) 0.0454(10) 0.0263(8) -0.0012(7) -0.0013(7) 0.0103(8)
C2 0.0160(7) 0.0260(8) 0.0200(7) -0.0073(6) 0.0040(5) -0.0013(6)
C3 0.0164(6) 0.0136(6) 0.0175(6) 0.0006(5) 0.0083(5) 0.0005(5)
C4 0.0179(7) 0.0194(7) 0.0244(7) 0.0045(5) 0.0127(6) 0.0024(5)
C5 0.0219(7) 0.0213(7) 0.0186(7) 0.0031(5) 0.0118(6) 0.0033(6)
C6 0.0165(7) 0.0172(7) 0.0205(7) -0.0012(5) 0.0035(5) -0.0029(5)
C7 0.0174(7) 0.0240(7) 0.0157(6) -0.0015(5) 0.0046(5) 0.0000(5)
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'
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
C3 N1 C4 108.58(11)
C3 N1 C2 124.83(11)
C4 N1 C2 126.57(11)
C3 N2 C5 108.75(11)
C3 N2 C6 125.25(11)
C5 N2 C6 125.51(11)
C7 N3 H3A 109.5
C7 N3 H3B 109.5
H3A N3 H3B 109.5
C7 N3 H3C 109.5
H3A N3 H3C 109.5
H3B N3 H3C 109.5
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C1 111.27(12)
N1 C2 H2A 109.4
C1 C2 H2A 109.4
N1 C2 H2B 109.4
C1 C2 H2B 109.4
H2A C2 H2B 108.0
N1 C3 N2 108.72(11)
N1 C3 H3 125.6
N2 C3 H3 125.6
C5 C4 N1 107.10(12)
C5 C4 H4 126.4
N1 C4 H4 126.4
C4 C5 N2 106.85(12)
C4 C5 H5 126.6
N2 C5 H5 126.6
N2 C6 C7 113.51(11)
N2 C6 H6A 108.9
C7 C6 H6A 108.9
N2 C6 H6B 108.9
C7 C6 H6B 108.9
H6A C6 H6B 107.7
N3 C7 C6 111.79(11)
N3 C7 H7A 109.3
C6 C7 H7A 109.3
N3 C7 H7B 109.3
C6 C7 H7B 109.3
H7A C7 H7B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.3264(17)
N1 C4 1.3779(17)
N1 C2 1.4670(17)
N2 C3 1.3264(16)
N2 C5 1.3777(17)
N2 C6 1.4648(16)
N3 C7 1.4845(17)
N3 H3A 0.8900
N3 H3B 0.8900
N3 H3C 0.8900
C1 C2 1.512(2)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9700
C2 H2B 0.9700
C3 H3 0.9300
C4 C5 1.3512(19)
C4 H4 0.9300
C5 H5 0.9300
C6 C7 1.5098(18)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9700
C7 H7B 0.9700
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
C3 N1 C2 C1 111.65(15)
C4 N1 C2 C1 -66.79(18)
C4 N1 C3 N2 -0.75(15)
C2 N1 C3 N2 -179.43(12)
C5 N2 C3 N1 0.41(15)
C6 N2 C3 N1 172.76(11)
C3 N1 C4 C5 0.80(15)
C2 N1 C4 C5 179.45(12)
N1 C4 C5 N2 -0.54(15)
C3 N2 C5 C4 0.09(15)
C6 N2 C5 C4 -172.23(12)
C3 N2 C6 C7 123.62(14)
C5 N2 C6 C7 -65.30(17)
N2 C6 C7 N3 -72.42(15)
