#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204331.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_7204331
loop_
_publ_author_name
'Wallfisch, Bianca C.'
'Belaj, Ferdinand'
'Wentrup, Curt'
'Kappe, C. Oliver'
'Kollenz, Gert'
_publ_section_title
;
 Synthesis and chemical reactivity of
 methoxycarbonyl-1,3-dioxinyl(pivaloyl)ketene---a persistent
 α-oxoketene
;
_journal_issue                   5
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              599
_journal_paper_doi               10.1039/b111143d
_journal_year                    2002
_chemical_formula_sum            'C21 H30 O7'
_chemical_formula_weight         394.45
_chemical_melting_point          378
_chemical_name_systematic
; 
2-(3,3-dimethyl-2-oxo-1-(oxomethylene)butyl)-2,6-di-tert-butyl-
-5-methoxycarbonyl-1,3-dioxin-4(2H)-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual edited SHELXL-97 .cif file'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.975(2)
_cell_length_b                   11.266(2)
_cell_length_c                   19.208(4)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      18.32
_cell_measurement_theta_min      15.05
_cell_volume                     2158.6(7)
_computing_cell_refinement       'local program'
_computing_data_collection       'local program'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      95(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe 4-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3197
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        1.1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0359
_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)+(0.0300P)²+0.1907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                2477
_reflns_number_total             2741
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b111143d.txt
_cod_data_source_block           6(BCW405)
_cod_database_code               7204331
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37942(15) -0.00337(12) 0.05187(7) 0.0172(3) Uani 1 1 d . . .
C2 C 0.4491(2) -0.05024(18) 0.11063(10) 0.0153(4) Uani 1 1 d . . .
O3 O 0.52736(14) 0.04118(12) 0.14257(7) 0.0166(3) Uani 1 1 d . . .
C4 C 0.4631(2) 0.14625(18) 0.15669(10) 0.0171(4) Uani 1 1 d . . .
O4 O 0.50984(15) 0.20914(14) 0.20091(7) 0.0242(4) Uani 1 1 d . . .
C5 C 0.3466(2) 0.17289(18) 0.11373(10) 0.0169(4) Uani 1 1 d . . .
C6 C 0.3141(2) 0.10061(18) 0.05997(11) 0.0173(4) Uani 1 1 d . . .
C11 C 0.3468(2) -0.09210(18) 0.16552(10) 0.0150(4) Uani 1 1 d . . .
C10 C 0.3799(2) -0.06248(19) 0.23019(10) 0.0180(5) Uani 1 1 d . . .
O10 O 0.41146(16) -0.03286(15) 0.28494(7) 0.0262(4) Uani 1 1 d . . .
C12 C 0.2174(2) -0.15090(19) 0.14921(11) 0.0186(5) Uani 1 1 d . . .
O12 O 0.19481(16) -0.18161(15) 0.08970(8) 0.0271(4) Uani 1 1 d . . .
C13 C 0.1112(2) -0.1676(2) 0.20648(11) 0.0218(5) Uani 1 1 d . . .
C14 C 0.0714(2) -0.0459(2) 0.23613(13) 0.0308(6) Uani 1 1 d . . .
H141 H 0.1501 -0.0081 0.2572 0.045(5) Uiso 1 1 calc R . .
H142 H 0.0017 -0.0563 0.2715 0.045(5) Uiso 1 1 calc R . .
H143 H 0.0371 0.0045 0.1985 0.045(5) Uiso 1 1 calc R . .
C15 C 0.1635(2) -0.2480(2) 0.26487(12) 0.0246(5) Uani 1 1 d . . .
H151 H 0.2414 -0.2107 0.2870 0.029(4) Uiso 1 1 calc R . .
H152 H 0.1898 -0.3249 0.2453 0.029(4) Uiso 1 1 calc R . .
H153 H 0.0928 -0.2599 0.2996 0.029(4) Uiso 1 1 calc R . .
C16 C -0.0111(2) -0.2264(3) 0.17376(14) 0.0386(7) Uani 1 1 d . . .
H161 H 0.0144 -0.3040 0.1548 0.053(5) Uiso 1 1 calc R . .
H162 H -0.0455 -0.1761 0.1362 0.053(5) Uiso 1 1 calc R . .
H163 H -0.0807 -0.2370 0.2092 0.053(5) Uiso 1 1 calc R . .
C20 C 0.5490(2) -0.14350(19) 0.08300(11) 0.0195(5) Uani 1 1 d . . .
C21 C 0.6243(2) -0.1981(2) 0.14438(12) 0.0300(6) Uani 1 1 d . . .
H211 H 0.6715 -0.1355 0.1699 0.037(4) Uiso 1 1 calc R . .
H212 H 0.6892 -0.2563 0.1271 0.037(4) Uiso 1 1 calc R . .
H213 H 0.5604 -0.2375 0.1755 0.037(4) Uiso 1 1 calc R . .
C22 C 0.6478(3) -0.0824(2) 0.03350(13) 0.0306(6) Uani 1 1 d . . .
H221 H 0.6952 -0.0192 0.0584 0.042(5) Uiso 1 1 calc R . .
H222 H 0.5986 -0.0482 -0.0059 0.042(5) Uiso 1 1 calc R . .
H223 H 0.7127 -0.1407 0.0163 0.042(5) Uiso 1 1 calc R . .
C23 C 0.4753(2) -0.2416(2) 0.04306(12) 0.0277(5) Uani 1 1 d . . .
H231 H 0.4113 -0.2809 0.0741 0.045(5) Uiso 1 1 calc R . .
H232 H 0.5404 -0.2999 0.0260 0.045(5) Uiso 1 1 calc R . .
H233 H 0.4272 -0.2068 0.0036 0.045(5) Uiso 1 1 calc R . .
C50 C 0.2734(2) 0.28354(19) 0.13273(11) 0.0205(5) Uani 1 1 d . . .
O50 O 0.15980(16) 0.28551(15) 0.15460(9) 0.0336(4) Uani 1 1 d . . .
O51 O 0.34962(16) 0.37945(13) 0.12422(8) 0.0247(4) Uani 1 1 d . . .
C51 C 0.2928(3) 0.4883(2) 0.15057(14) 0.0319(6) Uani 1 1 d . . .
H511 H 0.2098 0.5062 0.1253 0.044(5) Uiso 1 1 calc R . .
H512 H 0.3569 0.5532 0.1440 0.044(5) Uiso 1 1 calc R . .
H513 H 0.2731 0.4793 0.2003 0.044(5) Uiso 1 1 calc R . .
C60 C 0.2113(3) 0.1203(2) 0.00275(11) 0.0263(5) Uani 1 1 d . . .
C61 C 0.0732(2) 0.0822(3) 0.03027(14) 0.0371(6) Uani 1 1 d . . .
H611 H 0.0057 0.0937 -0.0062 0.039(4) Uiso 1 1 calc R . .
H612 H 0.0498 0.1304 0.0710 0.039(4) Uiso 1 1 calc R . .
H613 H 0.0760 -0.0017 0.0436 0.039(4) Uiso 1 1 calc R . .
C62 C 0.2470(3) 0.0445(3) -0.06046(12) 0.0465(8) Uani 1 1 d . . .
H621 H 0.1812 0.0581 -0.0975 0.051(5) Uiso 1 1 calc R . .
H622 H 0.2461 -0.0396 -0.0473 0.051(5) Uiso 1 1 calc R . .
H623 H 0.3365 0.0661 -0.0772 0.051(5) Uiso 1 1 calc R . .
C63 C 0.2069(3) 0.2506(2) -0.01979(14) 0.0414(7) Uani 1 1 d . . .
H631 H 0.1414 0.2602 -0.0574 0.057(5) Uiso 1 1 calc R . .
H632 H 0.2957 0.2748 -0.0363 0.057(5) Uiso 1 1 calc R . .
H633 H 0.1809 0.3001 0.0199 0.057(5) 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'
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
C6 O1 C2 117.73(16) . . yes
O1 C2 O3 109.79(16) . . yes
O1 C2 C11 109.39(16) . . ?
O3 C2 C11 106.75(15) . . ?
O1 C2 C20 107.14(15) . . ?
O3 C2 C20 106.58(16) . . ?
C11 C2 C20 117.04(17) . . yes
C4 O3 C2 116.77(15) . . yes
O4 C4 O3 117.85(19) . . yes
O4 C4 C5 126.11(19) . . yes
O3 C4 C5 115.99(17) . . yes
C6 C5 C4 119.95(19) . . yes
C6 C5 C50 124.91(19) . . yes
C4 C5 C50 115.12(18) . . yes
O1 C6 C5 119.61(19) . . yes
O1 C6 C60 111.68(18) . . yes
C5 C6 C60 128.7(2) . . yes
C10 C11 C12 121.70(19) . . yes
C10 C11 C2 113.50(18) . . yes
C12 C11 C2 124.61(17) . . yes
O10 C10 C11 177.1(2) . . yes
O12 C12 C11 119.13(19) . . yes
O12 C12 C13 120.66(19) . . yes
C11 C12 C13 120.15(17) . . yes
C16 C13 C15 108.47(19) . . ?
C16 C13 C14 109.5(2) . . ?
C15 C13 C14 110.14(18) . . ?
C16 C13 C12 108.01(18) . . ?
C15 C13 C12 111.15(18) . . ?
C14 C13 C12 109.51(17) . . ?
C13 C14 H141 109.5 . . ?
C13 C14 H142 109.5 . . ?
H141 C14 H142 109.5 . . ?
C13 C14 H143 109.5 . . ?
H141 C14 H143 109.5 . . ?
H142 C14 H143 109.5 . . ?
C13 C15 H151 109.5 . . ?
C13 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
C13 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
H152 C15 H153 109.5 . . ?
C13 C16 H161 109.5 . . ?
C13 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
C13 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
C21 C20 C22 110.09(19) . . ?
C21 C20 C23 109.38(19) . . ?
C22 C20 C23 108.76(18) . . ?
C21 C20 C2 109.05(17) . . ?
C22 C20 C2 108.84(18) . . ?
C23 C20 C2 110.70(18) . . ?
C20 C21 H211 109.5 . . ?
C20 C21 H212 109.5 . . ?
H211 C21 H212 109.5 . . ?
C20 C21 H213 109.5 . . ?
H211 C21 H213 109.5 . . ?
H212 C21 H213 109.5 . . ?
C20 C22 H221 109.5 . . ?
C20 C22 H222 109.5 . . ?
H221 C22 H222 109.5 . . ?
C20 C22 H223 109.5 . . ?
H221 C22 H223 109.5 . . ?
H222 C22 H223 109.5 . . ?
C20 C23 H231 109.5 . . ?
C20 C23 H232 109.5 . . ?
H231 C23 H232 109.5 . . ?
C20 C23 H233 109.5 . . ?
H231 C23 H233 109.5 . . ?
H232 C23 H233 109.5 . . ?
O50 C50 O51 124.3(2) . . yes
O50 C50 C5 124.1(2) . . yes
O51 C50 C5 111.67(17) . . yes
C50 O51 C51 114.99(17) . . yes
O51 C51 H511 109.5 . . ?
O51 C51 H512 109.5 . . ?
H511 C51 H512 109.5 . . ?
O51 C51 H513 109.5 . . ?
H511 C51 H513 109.5 . . ?
H512 C51 H513 109.5 . . ?
C6 C60 C62 109.6(2) . . ?
C6 C60 C63 111.4(2) . . ?
C62 C60 C63 108.6(2) . . ?
C6 C60 C61 108.39(18) . . ?
C62 C60 C61 109.0(2) . . ?
C63 C60 C61 109.9(2) . . ?
C60 C61 H611 109.5 . . ?
C60 C61 H612 109.5 . . ?
H611 C61 H612 109.5 . . ?
C60 C61 H613 109.5 . . ?
H611 C61 H613 109.5 . . ?
H612 C61 H613 109.5 . . ?
C60 C62 H621 109.5 . . ?
C60 C62 H622 109.5 . . ?
H621 C62 H622 109.5 . . ?
C60 C62 H623 109.5 . . ?
H621 C62 H623 109.5 . . ?
H622 C62 H623 109.5 . . ?
C60 C63 H631 109.5 . . ?
C60 C63 H632 109.5 . . ?
H631 C63 H632 109.5 . . ?
C60 C63 H633 109.5 . . ?
H631 C63 H633 109.5 . . ?
H632 C63 H633 109.5 . . ?
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 C2 1.427(2) . yes
O1 C6 1.349(2) . yes
C2 O3 1.431(2) . yes
C2 C11 1.541(3) . yes
C2 C20 1.542(3) . yes
O3 C4 1.373(2) . yes
C4 O4 1.200(2) . yes
C4 C5 1.456(3) . yes
C5 C6 1.354(3) . yes
C5 C50 1.490(3) . yes
C6 C60 1.520(3) . ?
C11 C10 1.328(3) . yes
C11 C12 1.484(3) . yes
C10 O10 1.147(3) . yes
C12 O12 1.215(3) . yes
C12 C13 1.539(3) . yes
C13 C16 1.524(3) . ?
C13 C15 1.534(3) . ?
C13 C14 1.537(3) . ?
C14 H141 0.9800 . ?
C14 H142 0.9800 . ?
C14 H143 0.9800 . ?
C15 H151 0.9800 . ?
C15 H152 0.9800 . ?
C15 H153 0.9800 . ?
C16 H161 0.9800 . ?
C16 H162 0.9800 . ?
C16 H163 0.9800 . ?
C20 C21 1.527(3) . ?
C20 C22 1.532(3) . ?
C20 C23 1.533(3) . ?
C21 H211 0.9800 . ?
C21 H212 0.9800 . ?
C21 H213 0.9800 . ?
C22 H221 0.9800 . ?
C22 H222 0.9800 . ?
C22 H223 0.9800 . ?
C23 H231 0.9800 . ?
C23 H232 0.9800 . ?
C23 H233 0.9800 . ?
C50 O50 1.209(3) . yes
C50 O51 1.331(3) . yes
O51 C51 1.442(3) . yes
C51 H511 0.9800 . ?
C51 H512 0.9800 . ?
C51 H513 0.9800 . ?
C60 C62 1.527(3) . ?
C60 C63 1.530(3) . ?
C60 C61 1.537(4) . ?
C61 H611 0.9800 . ?
C61 H612 0.9800 . ?
C61 H613 0.9800 . ?
C62 H621 0.9800 . ?
C62 H622 0.9800 . ?
C62 H623 0.9800 . ?
C63 H631 0.9800 . ?
C63 H632 0.9800 . ?
C63 H633 0.9800 . ?
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
C6 O1 C2 O3 -47.0(2) . . . . yes
O1 C2 O3 C4 49.8(2) . . . . yes
C2 O3 C4 C5 -25.0(2) . . . . yes
O3 C4 C5 C6 -5.2(3) . . . . yes
C4 C5 C6 O1 8.3(3) . . . . yes
C5 C6 O1 C2 19.1(3) . . . . yes
C6 O1 C2 C11 69.9(2) . . . . ?
C6 O1 C2 C20 -162.32(17) . . . . ?
C11 C2 O3 C4 -68.7(2) . . . . ?
C20 C2 O3 C4 165.47(16) . . . . ?
C2 O3 C4 O4 157.62(18) . . . . ?
O4 C4 C5 C6 172.0(2) . . . . ?
O4 C4 C5 C50 -6.5(3) . . . . ?
O3 C4 C5 C50 176.40(17) . . . . ?
C2 O1 C6 C60 -162.19(17) . . . . ?
C50 C5 C6 O1 -173.44(18) . . . . ?
C4 C5 C6 C60 -170.2(2) . . . . ?
C50 C5 C6 C60 8.1(4) . . . . ?
O1 C2 C11 C10 -137.29(19) . . . . ?
O3 C2 C11 C10 -18.6(2) . . . . yes
C20 C2 C11 C10 100.7(2) . . . . ?
O1 C2 C11 C12 37.8(3) . . . . ?
O3 C2 C11 C12 156.49(18) . . . . yes
C20 C2 C11 C12 -84.3(2) . . . . ?
C12 C11 C10 O10 -149(5) . . . . ?
C2 C11 C10 O10 26(5) . . . . ?
C10 C11 C12 O12 -176.3(2) . . . . ?
C2 C11 C12 O12 9.0(3) . . . . ?
C10 C11 C12 C13 6.3(3) . . . . ?
C2 C11 C12 C13 -168.32(19) . . . . ?
O12 C12 C13 C16 0.9(3) . . . . ?
C11 C12 C13 C16 178.2(2) . . . . yes
O12 C12 C13 C15 119.8(2) . . . . ?
C11 C12 C13 C15 -62.9(3) . . . . ?
O12 C12 C13 C14 -118.3(2) . . . . ?
C11 C12 C13 C14 59.0(3) . . . . ?
O1 C2 C20 C21 -178.92(17) . . . . yes
O3 C2 C20 C21 63.6(2) . . . . ?
C11 C2 C20 C21 -55.7(2) . . . . ?
O1 C2 C20 C22 61.0(2) . . . . ?
O3 C2 C20 C22 -56.5(2) . . . . ?
C11 C2 C20 C22 -175.84(18) . . . . ?
O1 C2 C20 C23 -58.5(2) . . . . ?
O3 C2 C20 C23 -176.02(16) . . . . ?
C11 C2 C20 C23 64.7(2) . . . . ?
C6 C5 C50 O50 66.7(3) . . . . ?
C4 C5 C50 O50 -115.0(2) . . . . ?
C6 C5 C50 O51 -114.8(2) . . . . ?
C4 C5 C50 O51 63.5(2) . . . . yes
O50 C50 O51 C51 6.8(3) . . . . yes
C5 C50 O51 C51 -171.74(19) . . . . ?
O1 C6 C60 C62 -21.5(3) . . . . ?
C5 C6 C60 C62 157.0(2) . . . . ?
O1 C6 C60 C63 -141.7(2) . . . . ?
C5 C6 C60 C63 36.9(3) . . . . ?
O1 C6 C60 C61 97.4(2) . . . . ?
C5 C6 C60 C61 -84.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189913
