#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/96/7019697.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_7019697
loop_
_publ_author_name
'Palomas, David'
'Holle, Sigrid'
'Inés, Blanca'
'Bruns, Hans'
'Goddard, Richard'
'Alcarazo, Manuel'
_publ_section_title
;
 Synthesis and reactivity of electron poor allenes: formation of
 completely organic frustrated Lewis pairs.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9073
_journal_page_last               9082
_journal_paper_doi               10.1039/c2dt30195d
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        dichloromethane
_chemical_formula_moiety         'C26 H40 N2 O8'
_chemical_formula_sum            'C26 H40 N2 O8'
_chemical_formula_weight         508.60
_chemical_name_systematic
;
2-(1,3-di(tert-butyl)imidazol-3-ium-2-yl)-
1,1,3,3-tetra-ethyloxycarbonyl-propan-2-ide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                HOS-HG-002-01
_audit_creation_date             2012-01-18
_cell_angle_alpha                90.00
_cell_angle_beta                 95.356(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3691(5)
_cell_length_b                   16.1875(9)
_cell_length_c                   15.839(1)
_cell_measurement_reflns_used    51445
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9997
_cell_measurement_theta_min      2.7537
_cell_volume                     2647.0(3)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48455
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         36.10
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.98596
_exptl_absorpt_correction_T_min  0.96822
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         6305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0360
_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)+(0.0490P)²+1.0780P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                5257
_reflns_number_total             6305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           6966_18
_cod_original_sg_symbol_Hall     '-c 2yc'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7019697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
O1 O 0.31897(5) 0.20950(3) 0.31591(3) 0.01852(10) Uani 1 1 d .
O2 O 0.38141(5) 0.18645(3) 0.18543(3) 0.01616(9) Uani 1 1 d .
O3 O 0.30859(5) -0.04402(3) 0.35011(3) 0.01657(9) Uani 1 1 d .
O4 O 0.18247(4) 0.06837(3) 0.32447(3) 0.01737(9) Uani 1 1 d .
N1 N 0.43396(5) -0.10581(3) 0.19166(3) 0.01152(8) Uani 1 1 d .
C1 C 0.5000 -0.05702(5) 0.2500 0.01054(12) Uani 1 2 d S
C2 C 0.45868(6) -0.18726(4) 0.21443(4) 0.01495(10) Uani 1 1 d .
H2 H 0.4245 -0.2337 0.1858 0.018 Uiso 1 1 calc R
C3 C 0.5000 0.03547(5) 0.2500 0.01022(12) Uani 1 2 d S
C4 C 0.39000(5) 0.07346(3) 0.27855(4) 0.01127(9) Uani 1 1 d .
C5 C 0.36050(6) 0.16262(4) 0.26499(4) 0.01317(10) Uani 1 1 d .
C6 C 0.35190(8) 0.27214(4) 0.16392(5) 0.02325(14) Uani 1 1 d .
H6B H 0.3976 0.3088 0.2049 0.028 Uiso 1 1 calc R
H6A H 0.2597 0.2823 0.1637 0.028 Uiso 1 1 calc R
C7 C 0.39519(8) 0.28670(4) 0.07688(5) 0.02230(13) Uani 1 1 d .
H7A H 0.3534 0.2477 0.0377 0.033 Uiso 1 1 calc R
H7C H 0.4874 0.2799 0.0788 0.033 Uiso 1 1 calc R
H7B H 0.3723 0.3418 0.0587 0.033 Uiso 1 1 calc R
C8 C 0.29534(5) 0.02584(4) 0.32115(4) 0.01189(9) Uani 1 1 d .
C9 C 0.08508(6) 0.03010(4) 0.37066(4) 0.01756(11) Uani 1 1 d .
H9B H 0.1235 0.0088 0.4245 0.021 Uiso 1 1 calc R
H9A H 0.0442 -0.0152 0.3383 0.021 Uiso 1 1 calc R
C10 C -0.01334(7) 0.09652(5) 0.38492(5) 0.02211(13) Uani 1 1 d .
H10A H -0.0513 0.1165 0.3312 0.033 Uiso 1 1 calc R
H10C H 0.0287 0.1413 0.4163 0.033 Uiso 1 1 calc R
H10B H -0.0799 0.0739 0.4163 0.033 Uiso 1 1 calc R
C11 C 0.34850(6) -0.08432(4) 0.11172(4) 0.01328(10) Uani 1 1 d .
C12 C 0.20791(6) -0.09039(4) 0.13304(5) 0.02006(12) Uani 1 1 d .
H12B H 0.1923 -0.0495 0.1748 0.030 Uiso 1 1 calc R
H12C H 0.1924 -0.1444 0.1550 0.030 Uiso 1 1 calc R
H12A H 0.1508 -0.0811 0.0827 0.030 Uiso 1 1 calc R
C13 C 0.37535(9) -0.14794(5) 0.04378(5) 0.02942(17) Uani 1 1 d .
H13B H 0.3473 -0.2015 0.0605 0.044 Uiso 1 1 calc R
H13C H 0.4665 -0.1494 0.0375 0.044 Uiso 1 1 calc R
H13A H 0.3290 -0.1328 -0.0093 0.044 Uiso 1 1 calc R
C14 C 0.37712(6) 0.00168(4) 0.07833(4) 0.01742(11) Uani 1 1 d .
H14A H 0.3319 0.0090 0.0231 0.026 Uiso 1 1 calc R
H14C H 0.4686 0.0074 0.0746 0.026 Uiso 1 1 calc R
H14B H 0.3488 0.0427 0.1163 0.026 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.1300
0.00 0.00 -1.00 0.1300
0.00 -1.00 0.00 0.0800
0.00 1.00 0.00 0.0900
-1.00 -1.00 0.00 0.2200
1.00 1.00 0.00 0.1800
1.00 -1.00 0.00 0.2100
-1.00 1.00 0.00 0.2000
1.00 -1.00 0.00 0.2000
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
O1 C5 O2 122.48(5) . . y
O1 C5 C4 126.25(6) . . y
O2 C5 C4 111.24(5) . . y
O2 C6 C7 106.81(6) . . y
O3 C8 O4 121.28(5) . . y
O3 C8 C4 127.15(5) . . y
O4 C8 C4 111.56(5) . . y
O4 C9 C10 106.54(5) . . y
N1 C1 N1 108.53(7) . 2_655 y
N1 C1 C3 125.73(3) 2_655 . y
N1 C1 C3 125.73(3) . . y
N1 C11 C12 107.19(5) . . y
N1 C11 C13 107.56(5) . . y
N1 C11 C14 112.37(5) . . y
C1 N1 C2 107.97(5) . . y
C1 N1 C11 130.98(5) . . y
C2 N1 C11 121.02(5) . . y
C2 C2 N1 107.75(3) 2_655 . y
C3 C4 C5 122.67(5) . . y
C3 C4 C8 121.15(5) . . y
C4 C3 C1 115.91(4) . . y
C4 C3 C1 115.91(4) 2_655 . y
C4 C3 C4 128.17(7) 2_655 . y
C5 O2 C6 116.18(5) . . y
C8 O4 C9 116.58(5) . . y
C8 C4 C5 116.14(5) . . y
C12 C11 C13 110.54(6) . . y
C14 C11 C12 110.77(5) . . y
C14 C11 C13 108.37(6) . . y
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 C5 1.2152(7) . y
O2 C5 1.3546(8) . y
O2 C6 1.4540(8) . y
O3 C8 1.2233(7) . y
O4 C8 1.3631(7) . y
O4 C9 1.4411(7) . y
N1 C1 1.3521(7) . y
N1 C2 1.3845(8) . y
N1 C11 1.5165(8) . y
C1 N1 1.3521(7) 2_655 y
C1 C3 1.4972(11) . y
C2 C2 1.3505(13) 2_655 y
C3 C4 1.4070(6) 2_655 y
C3 C4 1.4070(6) . y
C4 C5 1.4868(8) . y
C4 C8 1.4617(8) . y
C6 C7 1.5077(10) . y
C9 C10 1.5137(9) . y
C11 C12 1.5300(9) . y
C11 C13 1.5336(9) . y
C11 C14 1.5282(9) . y
