#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:32:17 +0100 (mar 22 de mar de 2016) $
#$Revision: 178903 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/32/4113240.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_4113240
loop_
_publ_author_name
'Dongbin Zhao'
'Zhaofu Fei'
'Tilmann J. Geldbach'
'Rosario Scopelliti'
'Paul J. Dyson'
_publ_section_title
;
 Nitrile-Functionalized Pyridinium Ionic Liquids: Synthesis,
 Characterization, and Their Application in Carbon-Carbon Coupling
 Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15876
_journal_page_last               15882
_journal_paper_doi               10.1021/ja0463482
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C9 H11 Cl N2'
_chemical_formula_weight         182.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.074(3)
_cell_length_b                   12.108(4)
_cell_length_c                   10.5053(16)
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      24.40515
_cell_measurement_theta_min      2.61775
_cell_volume                     949.1(5)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'marresearch, mar345'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'MAR345 IPDS'
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5684
_diffrn_reflns_theta_full        0.50
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       primatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.213(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0528
_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)+(0.0987P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1315
_reflns_number_total             1626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0463482si20040628_090334.cif
_cod_data_source_block           Compound1
_cod_database_code               4113240
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 0.81579(7) 1.04953(4) 0.59283(5) 0.0300(3) Uani 1 1 d .
N1 N 0.7636(2) 0.75269(14) 0.75298(17) 0.0252(5) Uani 1 1 d .
N2 N 1.3203(3) 1.08979(19) 1.0163(2) 0.0414(6) Uani 1 1 d .
C1 C 0.6159(3) 0.80789(18) 0.6738(2) 0.0284(5) Uani 1 1 d .
H1 H 0.6266 0.8708 0.6234 0.034 Uiso 1 1 calc R
C2 C 0.4483(3) 0.77397(19) 0.6649(2) 0.0313(5) Uani 1 1 d .
H2 H 0.3437 0.8126 0.6083 0.038 Uiso 1 1 calc R
C3 C 0.4357(3) 0.68259(19) 0.7401(2) 0.0316(6) Uani 1 1 d .
H3 H 0.3217 0.6574 0.7346 0.038 Uiso 1 1 calc R
C4 C 0.5900(3) 0.62826(18) 0.8232(2) 0.0291(5) Uani 1 1 d .
H4 H 0.5827 0.5664 0.8764 0.035 Uiso 1 1 calc R
C5 C 0.7538(3) 0.66423(18) 0.8283(2) 0.0276(5) Uani 1 1 d .
H5 H 0.8601 0.6270 0.8847 0.033 Uiso 1 1 calc R
C6 C 0.9417(3) 0.78957(18) 0.7568(2) 0.0293(5) Uani 1 1 d .
H6A H 0.9271 0.8224 0.6669 0.035 Uiso 1 1 calc R
H6B H 1.0222 0.7249 0.7727 0.035 Uiso 1 1 calc R
C7 C 1.0259(3) 0.87409(19) 0.8703(2) 0.0293(5) Uani 1 1 d .
H7A H 1.0524 0.8397 0.9614 0.035 Uiso 1 1 calc R
H7B H 0.9419 0.9362 0.8596 0.035 Uiso 1 1 calc R
C8 C 1.2000(3) 0.9168(2) 0.8604(2) 0.0328(6) Uani 1 1 d .
H8A H 1.2910 0.8572 0.8881 0.039 Uiso 1 1 calc R
H8B H 1.1767 0.9368 0.7637 0.039 Uiso 1 1 calc R
C9 C 1.2703(3) 1.0135(2) 0.9491(2) 0.0315(6) Uani 1 1 d .
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 0.0283(4) 0.0240(4) 0.0338(4) 0.00063(19) 0.0074(3) -0.00090(19)
N1 0.0273(10) 0.0222(9) 0.0259(9) -0.0002(7) 0.0099(7) 0.0011(7)
N2 0.0408(13) 0.0450(14) 0.0418(12) -0.0067(10) 0.0195(10) -0.0080(10)
C1 0.0359(13) 0.0234(11) 0.0255(11) 0.0031(8) 0.0113(9) 0.0029(9)
C2 0.0288(12) 0.0301(12) 0.0310(11) 0.0018(9) 0.0069(9) 0.0044(10)
C3 0.0294(12) 0.0337(13) 0.0306(12) -0.0038(9) 0.0100(9) -0.0034(10)
C4 0.0335(13) 0.0248(11) 0.0279(11) 0.0016(8) 0.0104(9) -0.0006(9)
C5 0.0334(13) 0.0224(11) 0.0255(10) 0.0015(8) 0.0098(9) 0.0004(9)
C6 0.0273(12) 0.0256(12) 0.0373(12) 0.0017(9) 0.0149(9) 0.0003(9)
C7 0.0266(12) 0.0309(12) 0.0289(11) 0.0007(9) 0.0089(9) -0.0014(9)
C8 0.0304(13) 0.0320(13) 0.0366(12) 0.0010(9) 0.0136(9) -0.0004(10)
C9 0.0256(12) 0.0391(14) 0.0305(11) 0.0019(10) 0.0114(9) -0.0022(10)
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
C1 N1 C5 121.4(2)
C1 N1 C6 119.12(18)
C5 N1 C6 119.52(19)
N1 C1 C2 120.6(2)
N1 C1 H1 119.7
C2 C1 H1 119.7
C1 C2 C3 118.8(2)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 119.6(2)
C4 C3 H3 120.2
C2 C3 H3 120.2
C5 C4 C3 119.7(2)
C5 C4 H4 120.2
C3 C4 H4 120.2
N1 C5 C4 119.9(2)
N1 C5 H5 120.0
C4 C5 H5 120.0
N1 C6 C7 111.15(18)
N1 C6 H6A 109.4
C7 C6 H6A 109.4
N1 C6 H6B 109.4
C7 C6 H6B 109.4
H6A C6 H6B 108.0
C6 C7 C8 108.68(18)
C6 C7 H7A 110.0
C8 C7 H7A 110.0
C6 C7 H7B 110.0
C8 C7 H7B 110.0
H7A C7 H7B 108.3
C9 C8 C7 111.6(2)
C9 C8 H8A 109.3
C7 C8 H8A 109.3
C9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108.0
N2 C9 C8 178.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.343(3)
N1 C5 1.352(3)
N1 C6 1.491(3)
N2 C9 1.139(3)
C1 C2 1.383(3)
C1 H1 0.9500
C2 C3 1.386(3)
C2 H2 0.9500
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.374(3)
C4 H4 0.9500
C5 H5 0.9500
C6 C7 1.520(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.537(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.469(3)
C8 H8A 0.9900
C8 H8B 0.9900
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
C5 N1 C1 C2 -1.4(3)
C6 N1 C1 C2 178.19(19)
N1 C1 C2 C3 0.5(3)
C1 C2 C3 C4 0.7(3)
C2 C3 C4 C5 -1.2(3)
C1 N1 C5 C4 0.9(3)
C6 N1 C5 C4 -178.65(19)
C3 C4 C5 N1 0.4(3)
C1 N1 C6 C7 90.0(2)
C5 N1 C6 C7 -90.4(2)
N1 C6 C7 C8 -174.81(18)
C6 C7 C8 C9 169.04(19)
