#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/96/7019699.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_7019699
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        liquid
_chemical_formula_moiety         'C15 H20 O8'
_chemical_formula_sum            'C15 H20 O8'
_chemical_formula_weight         328.31
_chemical_melting_point          276(2)
_chemical_name_systematic
;
1,1,3,3-tetra(ethoxylcarbonyl)allene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                HOS-HF-344-03
_audit_creation_date             2012-01-18
_cell_angle_alpha                100.459(2)
_cell_angle_beta                 95.176(2)
_cell_angle_gamma                102.972(2)
_cell_formula_units_Z            2
_cell_length_a                   4.7229(2)
_cell_length_b                   9.6401(5)
_cell_length_c                   19.1004(9)
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      64.0634
_cell_measurement_theta_min      4.7514
_cell_volume                     825.53(7)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18085
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.3001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0612
_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)+(0.0809P)²+0.6295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                2124
_reflns_number_total             2790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           6973_4
_cod_original_sg_symbol_Hall     '-p 1'
_cod_original_sg_symbol_H-M      'p -1'
_cod_database_code               7019699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.7647(6) 0.7608(3) 0.74932(13) 0.0325(6) Uani 1 1 d .
C2 C 0.8475(6) 0.8898(3) 0.79226(13) 0.0315(6) Uani 1 1 d .
C3 C 0.6664(6) 0.6340(3) 0.70579(13) 0.0326(6) Uani 1 1 d .
C4 C 1.0736(6) 0.9193(3) 0.85644(14) 0.0353(6) Uani 1 1 d .
C5 C 0.7044(6) 1.0076(3) 0.77765(14) 0.0361(6) Uani 1 1 d .
C6 C 0.4210(6) 0.5242(3) 0.72401(14) 0.0366(6) Uani 1 1 d .
C7 C 0.7820(6) 0.6008(3) 0.63538(14) 0.0356(6) Uani 1 1 d .
C8 C 1.3857(7) 0.8136(3) 0.92274(14) 0.0428(7) Uani 1 1 d .
H8A H 1.5046 0.9148 0.9400 0.051 Uiso 1 1 calc R
H8B H 1.5209 0.7504 0.9112 0.051 Uiso 1 1 calc R
C9 C 1.2166(8) 0.7664(4) 0.98066(16) 0.0546(8) Uani 1 1 d .
H9A H 1.0854 0.8302 0.9927 0.082 Uiso 1 1 calc R
H9B H 1.3533 0.7722 1.0235 0.082 Uiso 1 1 calc R
H9C H 1.1005 0.6658 0.9637 0.082 Uiso 1 1 calc R
C10 C 0.3833(8) 1.0695(4) 0.69216(19) 0.0599(9) Uani 1 1 d .
H10A H 0.3753 1.1455 0.7339 0.072 Uiso 1 1 calc R
H10B H 0.1796 1.0187 0.6704 0.072 Uiso 1 1 calc R
C11 C 0.5417(10) 1.1376(4) 0.6387(2) 0.0787(12) Uani 1 1 d .
H11A H 0.7369 1.1954 0.6617 0.118 Uiso 1 1 calc R
H11B H 0.4316 1.2010 0.6200 0.118 Uiso 1 1 calc R
H11C H 0.5615 1.0616 0.5991 0.118 Uiso 1 1 calc R
C12 C 0.2184(7) 0.4328(3) 0.82097(16) 0.0504(8) Uani 1 1 d .
H12A H 0.1303 0.3431 0.7842 0.060 Uiso 1 1 calc R
H12B H 0.0627 0.4836 0.8325 0.060 Uiso 1 1 calc R
C13 C 0.3512(9) 0.3961(4) 0.88688(17) 0.0587(9) Uani 1 1 d .
H13A H 0.5034 0.3451 0.8747 0.088 Uiso 1 1 calc R
H13B H 0.1989 0.3334 0.9066 0.088 Uiso 1 1 calc R
H13C H 0.4386 0.4858 0.9227 0.088 Uiso 1 1 calc R
C14 C 1.1396(7) 0.6969(3) 0.56515(15) 0.0458(7) Uani 1 1 d .
H14A H 1.1429 0.5939 0.5484 0.055 Uiso 1 1 calc R
H14B H 1.3447 0.7562 0.5753 0.055 Uiso 1 1 calc R
C15 C 0.9746(8) 0.7456(4) 0.50769(17) 0.0590(9) Uani 1 1 d .
H15A H 0.7737 0.6844 0.4964 0.088 Uiso 1 1 calc R
H15B H 1.0720 0.7372 0.4645 0.088 Uiso 1 1 calc R
H15C H 0.9697 0.8472 0.5245 0.088 Uiso 1 1 calc R
O1 O 1.1346(5) 1.0281(2) 0.90201(13) 0.0664(7) Uani 1 1 d .
O2 O 1.1868(4) 0.8053(2) 0.85826(9) 0.0419(5) Uani 1 1 d .
O3 O 0.7416(7) 1.1218(3) 0.81637(15) 0.0898(10) Uani 1 1 d .
O4 O 0.5323(6) 0.9664(2) 0.71578(12) 0.0623(7) Uani 1 1 d .
O5 O 0.2227(5) 0.4468(3) 0.68138(11) 0.0605(7) Uani 1 1 d .
O6 O 0.4530(4) 0.5273(2) 0.79401(10) 0.0451(5) Uani 1 1 d .
O7 O 0.6848(5) 0.4923(2) 0.59046(10) 0.0487(6) Uani 1 1 d .
O8 O 1.0027(4) 0.7117(2) 0.63087(9) 0.0420(5) Uani 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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_publ_flag
C3 C1 C2 176.5(3) y
C1 C2 C4 121.1(2) y
C1 C2 C5 119.2(2) y
C4 C2 C5 119.7(2) y
C1 C3 C6 119.4(2) y
C1 C3 C7 121.0(2) y
C6 C3 C7 119.5(2) y
O1 C4 O2 124.4(3) y
O1 C4 C2 124.5(3) y
O2 C4 C2 111.0(2) y
O3 C5 O4 124.5(3) y
O3 C5 C2 124.5(3) y
O4 C5 C2 111.0(2) y
O5 C6 O6 125.2(3) y
O5 C6 C3 124.4(2) y
O6 C6 C3 110.4(2) y
O7 C7 O8 126.1(2) y
O7 C7 C3 124.4(2) y
O8 C7 C3 109.5(2) y
O2 C8 C9 110.5(2) y
O4 C10 C11 109.8(3) y
O6 C12 C13 107.4(3) y
O8 C14 C15 110.6(3) y
C4 O2 C8 116.4(2) y
C5 O4 C10 118.2(2) y
C6 O6 C12 116.8(2) y
C7 O8 C14 116.5(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 1.307(3) y
C1 C2 1.314(3) y
C2 C4 1.492(4) y
C2 C5 1.500(4) y
C3 C6 1.498(4) y
C3 C7 1.505(4) y
C4 O1 1.195(3) y
C4 O2 1.330(3) y
C5 O3 1.176(3) y
C5 O4 1.314(3) y
C6 O5 1.194(3) y
C6 O6 1.326(3) y
C7 O7 1.195(3) y
C7 O8 1.337(3) y
C8 O2 1.459(3) y
C8 C9 1.499(4) y
C10 O4 1.451(4) y
C10 C11 1.481(5) y
C12 O6 1.464(3) y
C12 C13 1.491(5) y
C14 O8 1.462(3) y
C14 C15 1.493(5) y
