#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/49/4024936.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_4024936
loop_
_publ_author_name
'Bret R. Van Ausdall'
'Jeremy L. Glass'
'Kelly M. Wiggins'
'Atta M. Aarif'
'Janis Louie'
_publ_section_title
;
A Systematic Investigation of Factors Influencing the Decarboxylation of
Imidazolium Carboxylates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7935
_journal_page_last               7942
_journal_paper_doi               10.1021/jo901791k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C10 H16 N2 O2,0.33(C2 H3 N)'
_chemical_formula_sum            'C10.67 H17 N2.33 O2'
_chemical_formula_weight         209.93
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   18.7559(3)
_cell_length_b                   18.7559(3)
_cell_length_c                   16.2998(3)
_cell_measurement_reflns_used    11786
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     4965.79(14)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'WinGX, Ortep3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       'Phi and Omega scan'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4522
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9714
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0386
_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)+(0.0418P)²+4.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                2164
_reflns_number_total             2519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901791k_si_003.cif
_cod_data_source_block           jl017
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               4024936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31388(6) 0.19178(6) 0.37005(6) 0.0347(2) Uani 1 1 d . . .
O2 O 0.19771(7) 0.19436(6) 0.34016(6) 0.0374(3) Uani 1 1 d . . .
N1 N 0.22043(6) 0.02424(6) 0.29554(5) 0.0183(2) Uani 1 1 d . . .
N2 N 0.0000 0.0000 0.1804(2) 0.0574(8) Uani 1 3 d S . .
N3 N 0.19496(5) 0.08902(5) 0.20088(5) 0.0175(2) Uani 1 1 d . . .
C2 C 0.21945(7) 0.09374(7) 0.27875(6) 0.0186(2) Uani 1 1 d . . .
C4 C 0.18102(6) 0.01510(6) 0.16659(7) 0.0179(2) Uani 1 1 d . . .
C5 C 0.19547(6) -0.02649(6) 0.22665(6) 0.0177(2) Uani 1 1 d . . .
C6 C 0.24628(8) 0.16782(7) 0.33603(7) 0.0239(3) Uani 1 1 d . . .
C7 C 0.24422(8) 0.00448(7) 0.37517(7) 0.0247(3) Uani 1 1 d . . .
H7A H 0.2933(9) 0.0545(9) 0.3926(8) 0.027(4) Uiso 1 1 d . . .
H7B H 0.2604(9) -0.0364(9) 0.3647(8) 0.031(4) Uiso 1 1 d . . .
C8 C 0.17578(10) -0.02423(9) 0.43740(8) 0.0341(3) Uani 1 1 d . . .
H8A H 0.1623(10) 0.0192(11) 0.4480(10) 0.047(5) Uiso 1 1 d . . .
H8B H 0.1932(10) -0.0393(10) 0.4887(11) 0.047(5) Uiso 1 1 d . . .
H8C H 0.1253(10) -0.0732(10) 0.4159(9) 0.039(4) Uiso 1 1 d . . .
C9 C 0.18542(7) 0.15328(7) 0.15835(7) 0.0210(2) Uani 1 1 d . . .
H9A H 0.1590(9) 0.1716(9) 0.1973(9) 0.028(4) Uiso 1 1 d . . .
H9B H 0.1486(9) 0.1258(9) 0.1124(9) 0.028(4) Uiso 1 1 d . . .
C10 C 0.26663(8) 0.22265(8) 0.12906(10) 0.0341(3) Uani 1 1 d . . .
H10A H 0.3014(10) 0.2451(10) 0.1746(11) 0.042(4) Uiso 1 1 d . . .
H10B H 0.2586(10) 0.2658(10) 0.1013(10) 0.042(4) Uiso 1 1 d . . .
H10C H 0.2906(11) 0.2014(11) 0.0892(11) 0.054(5) Uiso 1 1 d . . .
C11 C 0.15842(8) -0.00649(8) 0.07892(7) 0.0247(3) Uani 1 1 d . . .
H11A H 0.1060(9) -0.0073(9) 0.0657(8) 0.030(4) Uiso 1 1 d . . .
H11B H 0.2012(9) 0.0328(9) 0.0425(9) 0.034(4) Uiso 1 1 d . . .
H11C H 0.1521(9) -0.0601(9) 0.0673(8) 0.029(4) Uiso 1 1 d . . .
C12 C 0.18751(8) -0.10938(7) 0.22669(7) 0.0226(3) Uani 1 1 d . . .
H12A H 0.2389(10) -0.1071(9) 0.2433(9) 0.036(4) Uiso 1 1 d . . .
H12B H 0.1450(9) -0.1442(9) 0.2669(9) 0.033(4) Uiso 1 1 d . . .
H12C H 0.1722(9) -0.1329(9) 0.1727(9) 0.030(4) Uiso 1 1 d . . .
C13 C 0.0000 0.0000 0.2507(3) 0.0503(8) Uani 1 3 d S . .
C14 C 0.0000 0.0000 0.3382(3) 0.0710(11) Uani 1 3 d S . .
H14 H 0.0475(14) 0.0528(14) 0.3590(14) 0.091(8) Uiso 1 1 d . . .
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'
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
_geom_angle_publ_flag
C2 N1 C5 109.65(9) . . ?
C2 N1 C7 125.12(9) . . ?
C5 N1 C7 125.23(9) . . ?
C2 N3 C4 109.51(9) . . ?
C2 N3 C9 124.69(9) . . ?
C4 N3 C9 125.80(9) . . ?
N3 C2 N1 107.49(9) . . ?
N3 C2 C6 125.68(9) . . ?
N1 C2 C6 126.74(10) . . ?
C5 C4 N3 106.85(9) . . ?
C5 C4 C11 130.25(10) . . ?
N3 C4 C11 122.84(10) . . ?
C4 C5 N1 106.47(9) . . ?
C4 C5 C12 130.97(10) . . ?
N1 C5 C12 122.56(9) . . ?
O2 C6 O1 130.69(11) . . ?
O2 C6 C2 115.00(10) . . ?
O1 C6 C2 114.31(10) . . ?
N1 C7 C8 111.73(11) . . ?
N1 C7 H7A 105.8(8) . . ?
C8 C7 H7A 112.0(8) . . ?
N1 C7 H7B 107.2(8) . . ?
C8 C7 H7B 112.5(9) . . ?
H7A C7 H7B 107.2(12) . . ?
C7 C8 H8A 110.4(10) . . ?
C7 C8 H8B 109.1(10) . . ?
H8A C8 H8B 110.3(14) . . ?
C7 C8 H8C 109.8(9) . . ?
H8A C8 H8C 107.8(14) . . ?
H8B C8 H8C 109.4(13) . . ?
N3 C9 C10 111.82(9) . . ?
N3 C9 H9A 105.9(8) . . ?
C10 C9 H9A 112.3(9) . . ?
N3 C9 H9B 105.9(8) . . ?
C10 C9 H9B 111.0(8) . . ?
H9A C9 H9B 109.8(12) . . ?
C9 C10 H10A 108.3(10) . . ?
C9 C10 H10B 110.2(9) . . ?
H10A C10 H10B 110.2(14) . . ?
C9 C10 H10C 109.3(11) . . ?
H10A C10 H10C 110.5(15) . . ?
H10B C10 H10C 108.2(14) . . ?
C4 C11 H11A 110.9(8) . . ?
C4 C11 H11B 111.4(9) . . ?
H11A C11 H11B 108.2(12) . . ?
C4 C11 H11C 109.9(8) . . ?
H11A C11 H11C 109.4(12) . . ?
H11B C11 H11C 107.0(12) . . ?
C5 C12 H12A 111.8(9) . . ?
C5 C12 H12B 108.6(9) . . ?
H12A C12 H12B 107.3(12) . . ?
C5 C12 H12C 109.3(9) . . ?
H12A C12 H12C 109.5(12) . . ?
H12B C12 H12C 110.3(12) . . ?
N2 C13 C14 180.000(1) . . ?
C13 C14 H14 109.7(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2439(15) . ?
O2 C6 1.2392(15) . ?
N1 C2 1.3409(14) . ?
N1 C5 1.3929(13) . ?
N1 C7 1.4787(14) . ?
N2 C13 1.146(5) . ?
N3 C2 1.3376(14) . ?
N3 C4 1.3930(14) . ?
N3 C9 1.4769(13) . ?
C2 C6 1.5350(15) . ?
C4 C5 1.3608(15) . ?
C4 C11 1.4880(15) . ?
C5 C12 1.4857(15) . ?
C7 C8 1.5084(18) . ?
C7 H7A 0.971(15) . ?
C7 H7B 0.969(15) . ?
C8 H8A 0.981(18) . ?
C8 H8B 0.989(18) . ?
C8 H8C 0.996(16) . ?
C9 C10 1.5029(17) . ?
C9 H9A 0.968(15) . ?
C9 H9B 0.973(14) . ?
C10 H10A 0.938(17) . ?
C10 H10B 1.003(17) . ?
C10 H10C 0.980(19) . ?
C11 H11A 0.999(15) . ?
C11 H11B 0.973(16) . ?
C11 H11C 0.970(15) . ?
C12 H12A 0.981(16) . ?
C12 H12B 0.985(15) . ?
C12 H12C 0.962(15) . ?
C13 C14 1.426(6) . ?
C14 H14 1.00(2) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C2 N1 -0.85(12) . . . . ?
C9 N3 C2 N1 179.82(9) . . . . ?
C4 N3 C2 C6 175.85(10) . . . . ?
C9 N3 C2 C6 -3.49(17) . . . . ?
C5 N1 C2 N3 -0.32(12) . . . . ?
C7 N1 C2 N3 179.81(10) . . . . ?
C5 N1 C2 C6 -176.97(10) . . . . ?
C7 N1 C2 C6 3.16(18) . . . . ?
C2 N3 C4 C5 1.70(12) . . . . ?
C9 N3 C4 C5 -178.98(10) . . . . ?
C2 N3 C4 C11 -175.88(10) . . . . ?
C9 N3 C4 C11 3.45(17) . . . . ?
N3 C4 C5 N1 -1.82(12) . . . . ?
C11 C4 C5 N1 175.51(11) . . . . ?
N3 C4 C5 C12 177.42(11) . . . . ?
C11 C4 C5 C12 -5.2(2) . . . . ?
C2 N1 C5 C4 1.36(12) . . . . ?
C7 N1 C5 C4 -178.76(10) . . . . ?
C2 N1 C5 C12 -177.96(10) . . . . ?
C7 N1 C5 C12 1.92(16) . . . . ?
N3 C2 C6 O2 50.79(16) . . . . ?
N1 C2 C6 O2 -133.15(12) . . . . ?
N3 C2 C6 O1 -128.52(12) . . . . ?
N1 C2 C6 O1 47.55(16) . . . . ?
C2 N1 C7 C8 78.51(14) . . . . ?
C5 N1 C7 C8 -101.35(13) . . . . ?
C2 N3 C9 C10 79.95(14) . . . . ?
C4 N3 C9 C10 -99.28(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659056
