#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/58/4505890.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_4505890
loop_
_publ_author_name
'Laus, Gerhard'
'Bentivoglio, Gino'
'Kahlenberg, Volker'
'Wurst, Klaus'
'Nauer, Gerhard'
'Schottenberger, Herwig'
'Tanaka, Masato'
'Siehl, Hans-Ullrich'
_publ_section_title
;
 Conformational Flexibility and Cation--Anion Interactions in
 1-Butyl-2,3-dimethylimidazolium Salts
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1838
_journal_paper_doi               10.1021/cg201424m
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C9 H17 N2, N3'
_chemical_formula_sum            'C9 H17 N5'
_chemical_formula_weight         195.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000
_cell_angle_beta                 106.56(2)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   8.723(2)
_cell_length_b                   11.689(2)
_cell_length_c                   11.205(2)
_cell_measurement_reflns_used    6483
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.6
_cell_volume                     1095.1(4)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8089
_diffrn_reflns_theta_full        26.95
_diffrn_reflns_theta_max         26.95
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.016(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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0410
_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)+(0.0442P)²+0.2019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1801
_reflns_number_total             2323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201424m_si_003.cif
_cod_data_source_block           bmmi_azide
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4505890
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.60090(13) 0.47027(9) 0.67281(10) 0.0372(3) Uani 1 1 d .
N3 N 0.70001(12) 0.38998(10) 0.53822(10) 0.0362(3) Uani 1 1 d .
C7 C 0.69083(17) 0.52721(12) 0.89515(13) 0.0422(3) Uani 1 1 d .
H7A H 0.6756 0.5870 0.9533 0.051 Uiso 1 1 calc R
H7B H 0.8015 0.5341 0.8891 0.051 Uiso 1 1 calc R
C2 C 0.71293(15) 0.48062(11) 0.61283(12) 0.0355(3) Uani 1 1 d .
N5 N 1.08006(14) 0.35556(10) 0.75235(10) 0.0409(3) Uani 1 1 d .
N6 N 0.98045(16) 0.33624(12) 0.80280(13) 0.0540(4) Uani 1 1 d .
C5 C 0.51745(16) 0.36990(12) 0.63631(13) 0.0403(3) Uani 1 1 d .
H5 H 0.4323 0.3416 0.6651 0.048 Uiso 1 1 calc R
C4 C 0.57926(16) 0.31962(12) 0.55228(13) 0.0394(3) Uani 1 1 d .
H4 H 0.5461 0.2492 0.5106 0.047 Uiso 1 1 calc R
C8 C 0.67136(18) 0.41070(12) 0.94884(13) 0.0448(4) Uani 1 1 d .
H8A H 0.5589 0.4012 0.9496 0.054 Uiso 1 1 calc R
H8B H 0.6950 0.3505 0.8944 0.054 Uiso 1 1 calc R
C10 C 0.82855(17) 0.57535(13) 0.62517(14) 0.0443(3) Uani 1 1 d .
H10A H 0.9346 0.5498 0.6747 0.066 Uiso 1 1 calc R
H10B H 0.7944 0.6403 0.6667 0.066 Uiso 1 1 calc R
H10C H 0.8333 0.5988 0.5423 0.066 Uiso 1 1 calc R
C6 C 0.57523(18) 0.54915(12) 0.76778(14) 0.0454(4) Uani 1 1 d .
H6A H 0.4643 0.5405 0.7727 0.054 Uiso 1 1 calc R
H6B H 0.5884 0.6289 0.7425 0.054 Uiso 1 1 calc R
N4 N 1.17643(17) 0.37594(13) 0.70187(13) 0.0585(4) Uani 1 1 d .
C9 C 0.7801(2) 0.39484(14) 1.07978(14) 0.0542(4) Uani 1 1 d .
H9A H 0.8919 0.3986 1.0787 0.081 Uiso 1 1 calc R
H9B H 0.7593 0.3202 1.1118 0.081 Uiso 1 1 calc R
H9C H 0.7594 0.4555 1.1336 0.081 Uiso 1 1 calc R
C11 C 0.80391(17) 0.36468(14) 0.45913(13) 0.0456(4) Uani 1 1 d .
H11A H 0.8153 0.4334 0.4123 0.068 Uiso 1 1 calc R
H11B H 0.7564 0.3031 0.4009 0.068 Uiso 1 1 calc R
H11C H 0.9093 0.3406 0.5114 0.068 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'
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
C2 N1 C5 109.07(11)
C2 N1 C6 126.07(12)
C5 N1 C6 124.79(11)
C2 N3 C4 109.42(11)
C2 N3 C11 125.60(11)
C4 N3 C11 124.88(12)
C6 C7 C8 113.91(12)
C6 C7 H7A 108.8
C8 C7 H7A 108.8
C6 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.7
N3 C2 N1 107.40(11)
N3 C2 C10 125.96(12)
N1 C2 C10 126.63(12)
N4 N5 N6 178.94(15)
C4 C5 N1 107.21(12)
C4 C5 H5 126.4
N1 C5 H5 126.4
C5 C4 N3 106.89(12)
C5 C4 H4 126.6
N3 C4 H4 126.6
C9 C8 C7 112.58(13)
C9 C8 H8A 109.1
C7 C8 H8A 109.1
C9 C8 H8B 109.1
C7 C8 H8B 109.1
H8A C8 H8B 107.8
C2 C10 H10A 109.5
C2 C10 H10B 109.5
H10A C10 H10B 109.5
C2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N1 C6 C7 112.14(11)
N1 C6 H6A 109.2
C7 C6 H6A 109.2
N1 C6 H6B 109.2
C7 C6 H6B 109.2
H6A C6 H6B 107.9
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
N3 C11 H11A 109.5
N3 C11 H11B 109.5
H11A C11 H11B 109.5
N3 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3400(16)
N1 C5 1.3798(18)
N1 C6 1.4727(17)
N3 C2 1.3343(17)
N3 C4 1.3803(17)
N3 C11 1.4669(16)
C7 C6 1.516(2)
C7 C8 1.518(2)
C7 H7A 0.9900
C7 H7B 0.9900
C2 C10 1.4775(19)
N5 N4 1.1638(17)
N5 N6 1.1855(17)
C4 C5 1.346(2)
C5 H5 0.9500
C4 H4 0.9500
C8 C9 1.514(2)
C8 H8A 0.9900
C8 H8B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C6 H6A 0.9900
C6 H6B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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
C4 N3 C2 N1 -0.95(14)
C11 N3 C2 N1 -177.42(11)
C4 N3 C2 C10 179.78(13)
C11 N3 C2 C10 3.3(2)
C5 N1 C2 N3 0.93(14)
C6 N1 C2 N3 177.78(12)
C5 N1 C2 C10 -179.81(13)
C6 N1 C2 C10 -3.0(2)
C2 N1 C5 C4 -0.55(15)
C6 N1 C5 C4 -177.45(12)
N1 C5 C4 N3 -0.04(15)
C2 N3 C4 C5 0.62(15)
C11 N3 C4 C5 177.12(12)
C6 C7 C8 C9 -175.81(12)
C2 N1 C6 C7 -80.85(16)
C5 N1 C6 C7 95.53(15)
C8 C7 C6 N1 -64.02(15)
