#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:07:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208149.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_7208149
loop_
_publ_author_name
'Sánchez, Ignacio'
'Campo, José Antonio'
'Heras, José Vicente'
'Rosario Torres, M.'
'Cano, Mercedes'
_publ_section_title
;
 Pyrazolium salts as a new class of ionic liquid crystals
;
_journal_issue                   26
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              13239
_journal_paper_doi               10.1039/c2jm31939j
_journal_volume                  22
_journal_year                    2012
_chemical_formula_sum            'C10 H11 Cl N2 O'
_chemical_formula_weight         210.66
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9981(19)
_cell_length_b                   7.3161(12)
_cell_length_c                   23.079(3)
_cell_measurement_reflns_used    1087
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      2.45
_cell_volume                     2025.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0912
_diffrn_reflns_av_sigmaI/netI    0.1026
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11540
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0428
_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)+(0.0300P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                943
_reflns_number_total             2138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2jm31939j.txt
_cod_data_source_block           C10H11ClN2O
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7208149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
Cl Cl 0.41701(6) 1.20070(11) 0.55620(4) 0.0550(3) Uani 1 1 d .
N1 N 0.2998(2) 1.0117(3) 0.45715(11) 0.0452(7) Uani 1 1 d .
H1 H 0.3292 1.0689 0.4890 0.054 Uiso 1 1 d R
O1 O 0.45072(16) 0.7443(3) 0.14426(10) 0.0480(6) Uani 1 1 d .
N2 N 0.3605(2) 0.9714(3) 0.40968(11) 0.0396(7) Uani 1 1 d .
H2 H 0.4334 0.9381 0.4155 0.048 Uiso 1 1 d R
C3 C 0.2934(2) 0.9419(4) 0.36441(14) 0.0330(8) Uani 1 1 d .
C4 C 0.1850(2) 0.9693(4) 0.38440(14) 0.0407(9) Uani 1 1 d .
H4 H 0.1197 0.9590 0.3629 0.049 Uiso 1 1 calc R
C5 C 0.1931(3) 1.0142(4) 0.44164(15) 0.0471(9) Uani 1 1 d .
H5 H 0.1336 1.0420 0.4659 0.057 Uiso 1 1 calc R
C6 C 0.3343(2) 0.8897(4) 0.30749(13) 0.0312(7) Uani 1 1 d .
C7 C 0.4393(2) 0.8115(4) 0.29889(13) 0.0376(8) Uani 1 1 d .
H7 H 0.4859 0.7915 0.3305 0.045 Uiso 1 1 calc R
C8 C 0.4744(2) 0.7638(4) 0.24411(14) 0.0395(8) Uani 1 1 d .
H8 H 0.5439 0.7096 0.2391 0.047 Uiso 1 1 calc R
C9 C 0.4071(2) 0.7959(4) 0.19628(13) 0.0342(7) Uani 1 1 d .
C10 C 0.3030(2) 0.8758(4) 0.20381(13) 0.0370(8) Uani 1 1 d .
H10 H 0.2572 0.8981 0.1721 0.044 Uiso 1 1 calc R
C11 C 0.2683(2) 0.9217(4) 0.25909(14) 0.0380(8) Uani 1 1 d .
H11 H 0.1987 0.9756 0.2640 0.046 Uiso 1 1 calc R
C12 C 0.3886(3) 0.7873(4) 0.09307(13) 0.0582(10) Uani 1 1 d .
H13C H 0.3161 0.7321 0.0954 0.087 Uiso 1 1 calc R
H12B H 0.4272 0.7412 0.0597 0.087 Uiso 1 1 calc R
H12A H 0.3807 0.9175 0.0898 0.087 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
Cl 0.0492(5) 0.0590(5) 0.0568(7) -0.0130(5) -0.0151(5) 0.0128(4)
N1 0.0484(17) 0.0520(17) 0.035(2) -0.0097(13) -0.0005(15) -0.0007(14)
O1 0.0473(14) 0.0641(15) 0.0325(15) -0.0030(12) 0.0028(12) 0.0047(10)
N2 0.0316(14) 0.0468(15) 0.0404(19) -0.0065(14) -0.0030(14) 0.0032(12)
C3 0.0308(17) 0.0329(17) 0.035(2) -0.0009(15) -0.0066(16) -0.0017(13)
C4 0.0336(17) 0.050(2) 0.038(2) -0.0009(17) -0.0004(17) -0.0005(15)
C5 0.040(2) 0.052(2) 0.049(3) -0.0016(19) 0.009(2) -0.0017(16)
C6 0.0297(16) 0.0330(16) 0.031(2) -0.0013(14) -0.0007(16) -0.0020(13)
C7 0.0328(17) 0.0377(17) 0.042(2) -0.0014(16) -0.0086(16) 0.0002(14)
C8 0.0311(17) 0.0400(19) 0.048(2) -0.0028(17) 0.0007(17) 0.0011(14)
C9 0.0350(17) 0.0337(16) 0.034(2) 0.0003(16) 0.0010(17) -0.0014(14)
C10 0.0377(18) 0.0411(18) 0.032(2) 0.0073(16) -0.0060(16) 0.0024(15)
C11 0.0299(17) 0.0418(19) 0.042(2) 0.0022(17) -0.0019(17) 0.0014(14)
C12 0.076(3) 0.062(2) 0.037(2) -0.0004(19) 0.001(2) 0.010(2)
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'
O O 0.0106 0.0060 '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
C5 N1 N2 107.7(3)
C5 N1 H1 125.5
N2 N1 H1 122.9
C9 O1 C12 117.7(2)
C3 N2 N1 110.2(2)
C3 N2 H2 130.2
N1 N2 H2 117.0
N2 C3 C4 106.2(3)
N2 C3 C6 123.1(3)
C4 C3 C6 130.7(3)
C5 C4 C3 106.7(3)
C5 C4 H4 126.6
C3 C4 H4 126.6
N1 C5 C4 109.1(3)
N1 C5 H5 125.5
C4 C5 H5 125.5
C11 C6 C7 117.9(3)
C11 C6 C3 119.4(3)
C7 C6 C3 122.7(3)
C8 C7 C6 120.6(3)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.6(3)
C7 C8 H8 119.7
C9 C8 H8 119.7
O1 C9 C8 115.5(3)
O1 C9 C10 124.9(3)
C8 C9 C10 119.7(3)
C11 C10 C9 119.2(3)
C11 C10 H10 120.4
C9 C10 H10 120.4
C10 C11 C6 122.0(3)
C10 C11 H11 119.0
C6 C11 H11 119.0
O1 C12 H13C 109.5
O1 C12 H12B 109.5
H13C C12 H12B 109.5
O1 C12 H12A 109.5
H13C C12 H12A 109.5
H12B C12 H12A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.329(3)
N1 N2 1.348(3)
N1 H1 0.9175
O1 C9 1.363(3)
O1 C12 1.432(3)
N2 C3 1.336(3)
N2 H2 0.9185
C3 C4 1.395(4)
C3 C6 1.453(4)
C4 C5 1.365(4)
C4 H4 0.9300
C5 H5 0.9300
C6 C11 1.389(3)
C6 C7 1.399(4)
C7 C8 1.377(3)
C7 H7 0.9300
C8 C9 1.388(4)
C8 H8 0.9300
C9 C10 1.389(4)
C10 C11 1.383(3)
C10 H10 0.9300
C11 H11 0.9300
C12 H13C 0.9600
C12 H12B 0.9600
C12 H12A 0.9600
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
_geom_hbond_site_symmetry_A
N1 H1 Cl 0.92 2.11 3.019(3) 172.4 .
N2 H2 Cl 0.92 2.16 3.055(2) 163.6 5_676
C4 H4 O1 0.93 2.57 3.324(4) 138.4 6_556
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 N2 C3 -2.1(3)
N1 N2 C3 C4 1.4(3)
N1 N2 C3 C6 -178.0(2)
N2 C3 C4 C5 -0.2(3)
C6 C3 C4 C5 179.1(3)
N2 N1 C5 C4 2.0(3)
C3 C4 C5 N1 -1.1(3)
N2 C3 C6 C11 -158.0(3)
C4 C3 C6 C11 22.8(4)
N2 C3 C6 C7 20.5(4)
C4 C3 C6 C7 -158.6(3)
C11 C6 C7 C8 -1.6(4)
C3 C6 C7 C8 179.8(2)
C6 C7 C8 C9 1.3(4)
C12 O1 C9 C8 -175.2(2)
C12 O1 C9 C10 4.8(4)
C7 C8 C9 O1 179.6(2)
C7 C8 C9 C10 -0.4(4)
O1 C9 C10 C11 179.9(2)
C8 C9 C10 C11 -0.1(4)
C9 C10 C11 C6 -0.2(4)
C7 C6 C11 C10 1.1(4)
C3 C6 C11 C10 179.7(2)
