#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111753.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111753
loop_
_publ_author_name
'Iwata, Shin'
'Hamura, Toshiyuki'
'Suzuki, Keisuke'
_publ_section_title
;
 Siloxy(trialkoxy)ethene undergoes regioselective [2+2] cycloaddition to
 ynones and ynoates en route to functionalized cyclobutenediones
;
_journal_issue                   29
_journal_name_full               'Chemical Communications'
_journal_page_first              5316
_journal_page_last               5318
_journal_paper_doi               10.1039/c0cc00883d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C19 H16 O5'
_chemical_formula_sum            'C19 H16 O5'
_chemical_formula_weight         324.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.071(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8511(9)
_cell_length_b                   9.3112(9)
_cell_length_c                   18.1359(17)
_cell_measurement_reflns_used    11394
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.10
_cell_volume                     1637.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT & SADABS'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11394
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'rotating anode x-ray tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0405
_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)+(0.0463P)²+0.4326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                3318
_reflns_number_total             3762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00883Dsup1.cif
_cod_data_source_block           iwata
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7111753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
H17 H -0.3431(14) 1.0003(16) 0.0057(7) 0.035(3) Uiso 1 1 d
H7 H 0.3971(15) 0.7356(17) 0.2623(9) 0.045(4) Uiso 1 1 d
H10 H 0.5854(15) 0.6148(16) 0.0508(8) 0.043(4) Uiso 1 1 d
H11 H 0.3822(15) 0.7511(16) 0.0389(9) 0.043(4) Uiso 1 1 d
H13 H -0.0739(15) 0.6667(16) 0.0081(8) 0.041(4) Uiso 1 1 d
H8 H 0.6033(17) 0.5974(18) 0.2775(10) 0.056(4) Uiso 1 1 d
H14 H -0.2310(16) 0.5547(18) -0.0889(9) 0.050(4) Uiso 1 1 d
H15 H -0.4442(16) 0.6576(16) -0.1339(9) 0.045(4) Uiso 1 1 d
H9 H 0.6977(16) 0.5384(16) 0.1708(8) 0.042(4) Uiso 1 1 d
H16 H -0.4995(17) 0.8895(17) -0.0891(8) 0.048(4) Uiso 1 1 d
H19A H -0.307(2) 0.957(2) 0.2352(10) 0.071(5) Uiso 1 1 d
H19B H -0.2063(19) 0.859(2) 0.1965(11) 0.068(5) Uiso 1 1 d
H18C H -0.150(2) 1.387(2) 0.0634(12) 0.075(6) Uiso 1 1 d
H19C H -0.142(2) 0.979(3) 0.2530(13) 0.094(7) Uiso 1 1 d
H18B H -0.204(2) 1.322(2) 0.1349(12) 0.081(6) Uiso 1 1 d
H18A H -0.048(2) 1.325(2) 0.1338(13) 0.091(7) Uiso 1 1 d
C1 C 0.02954(10) 0.90324(12) 0.11337(6) 0.0301(2) Uani 1 1 d
C2 C -0.10129(10) 0.91962(11) 0.07401(6) 0.0266(2) Uani 1 1 d
C3 C -0.12779(10) 1.05965(11) 0.11422(6) 0.0294(2) Uani 1 1 d
C4 C 0.02296(11) 1.03598(12) 0.15764(7) 0.0352(3) Uani 1 1 d
C5 C 0.13656(10) 0.79173(12) 0.11583(6) 0.0309(2) Uani 1 1 d
C6 C 0.37593(10) 0.75515(11) 0.15032(6) 0.0288(2) Uani 1 1 d
C7 C 0.43743(12) 0.71083(13) 0.22053(7) 0.0345(2) Uani 1 1 d
C8 C 0.55803(12) 0.62991(14) 0.22775(7) 0.0376(3) Uani 1 1 d
C9 C 0.61305(11) 0.59553(13) 0.16523(7) 0.0339(2) Uani 1 1 d
C10 C 0.54773(12) 0.63858(13) 0.09483(7) 0.0353(2) Uani 1 1 d
C11 C 0.42766(12) 0.71972(13) 0.08687(7) 0.0343(2) Uani 1 1 d
C12 C -0.19359(10) 0.84536(11) 0.01582(6) 0.0253(2) Uani 1 1 d
C13 C -0.16109(11) 0.71198(12) -0.01251(6) 0.0311(2) Uani 1 1 d
C14 C -0.25370(12) 0.64522(13) -0.06802(7) 0.0353(2) Uani 1 1 d
C15 C -0.37899(12) 0.70952(13) -0.09608(6) 0.0346(2) Uani 1 1 d
C16 C -0.41259(11) 0.84159(13) -0.06898(6) 0.0331(2) Uani 1 1 d
C17 C -0.32082(11) 0.90915(12) -0.01321(6) 0.0287(2) Uani 1 1 d
C18 C -0.13866(19) 1.31267(15) 0.10189(11) 0.0533(4) Uani 1 1 d
C19 C -0.22251(19) 0.95346(17) 0.21388(10) 0.0522(4) Uani 1 1 d
O1 O 0.26075(7) 0.84746(9) 0.14481(5) 0.0356(2) Uani 1 1 d
O2 O 0.11792(8) 0.66902(9) 0.09749(6) 0.0480(3) Uani 1 1 d
O3 O -0.14756(8) 1.17521(8) 0.06541(5) 0.0360(2) Uani 1 1 d
O4 O -0.23511(8) 1.05861(9) 0.15561(5) 0.0361(2) Uani 1 1 d
O5 O 0.09759(10) 1.09941(11) 0.20622(6) 0.0564(3) 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 0.0033 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
C2 C1 C5 134.22(10)
C2 C1 C4 93.63(9)
C5 C1 C4 132.05(10)
C1 C2 C12 138.04(10)
C1 C2 C3 93.99(8)
C12 C2 C3 127.97(9)
O3 C3 O4 108.25(8)
O3 C3 C2 111.83(9)
O4 C3 C2 117.08(9)
O3 C3 C4 116.39(9)
O4 C3 C4 117.84(9)
C2 C3 C4 83.96(7)
O5 C4 C1 136.85(11)
O5 C4 C3 134.73(11)
C1 C4 C3 88.42(8)
O2 C5 O1 124.14(10)
O2 C5 C1 126.19(10)
O1 C5 C1 109.63(9)
C7 C6 C11 122.31(10)
C7 C6 O1 117.81(10)
C11 C6 O1 119.76(10)
C6 C7 C8 118.68(11)
C6 C7 H7 119.4(9)
C8 C7 H7 121.9(9)
C9 C8 C7 120.00(11)
C9 C8 H8 120.2(10)
C7 C8 H8 119.8(10)
C8 C9 C10 120.37(10)
C8 C9 H9 119.5(8)
C10 C9 H9 120.1(8)
C9 C10 C11 120.20(11)
C9 C10 H10 120.9(9)
C11 C10 H10 118.9(9)
C6 C11 C10 118.41(11)
C6 C11 H11 120.4(9)
C10 C11 H11 121.2(9)
C13 C12 C17 118.91(10)
C13 C12 C2 122.50(9)
C17 C12 C2 118.59(9)
C14 C13 C12 120.08(10)
C14 C13 H13 120.8(9)
C12 C13 H13 119.1(9)
C13 C14 C15 120.33(11)
C13 C14 H14 120.6(10)
C15 C14 H14 119.0(10)
C16 C15 C14 120.39(11)
C16 C15 H15 121.2(9)
C14 C15 H15 118.4(9)
C17 C16 C15 119.76(10)
C17 C16 H16 118.9(9)
C15 C16 H16 121.3(9)
C16 C17 C12 120.53(10)
C16 C17 H17 120.3(8)
C12 C17 H17 119.2(8)
O3 C18 H18C 108.2(12)
O3 C18 H18B 111.9(13)
H18C C18 H18B 112.3(17)
O3 C18 H18A 110.7(13)
H18C C18 H18A 108.3(17)
H18B C18 H18A 105.4(18)
O4 C19 H19A 107.5(11)
O4 C19 H19B 112.5(12)
H19A C19 H19B 111.5(16)
O4 C19 H19C 108.6(13)
H19A C19 H19C 109.5(17)
H19B C19 H19C 107.2(18)
C5 O1 C6 117.14(8)
C3 O3 C18 114.04(11)
C3 O4 C19 115.15(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3683(14)
C1 C5 1.4748(14)
C1 C4 1.4814(15)
C2 C12 1.4432(14)
C2 C3 1.5383(14)
C3 O3 1.3853(14)
C3 O4 1.3995(13)
C3 C4 1.5700(15)
C4 O5 1.1996(14)
C5 O2 1.1952(14)
C5 O1 1.3481(13)
C6 C7 1.3744(16)
C6 C11 1.3776(16)
C6 O1 1.4130(12)
C7 C8 1.3935(16)
C7 H7 0.943(15)
C8 C9 1.3773(17)
C8 H8 0.981(17)
C9 C10 1.3846(17)
C9 H9 0.979(15)
C10 C11 1.3896(16)
C10 H10 0.963(15)
C11 H11 0.952(15)
C12 C13 1.4022(14)
C12 C17 1.4036(14)
C13 C14 1.3824(16)
C13 H13 0.971(15)
C14 C15 1.3861(17)
C14 H14 0.966(16)
C15 C16 1.3856(17)
C15 H15 0.982(16)
C16 C17 1.3844(16)
C16 H16 0.978(16)
C17 H17 0.955(14)
C18 O3 1.4364(15)
C18 H18C 0.98(2)
C18 H18B 0.96(2)
C18 H18A 0.98(2)
C19 O4 1.4300(18)
C19 H19A 0.97(2)
C19 H19B 0.95(2)
C19 H19C 0.99(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
C5 C1 C2 C12 -3.8(2)
C4 C1 C2 C12 179.73(13)
C5 C1 C2 C3 176.33(13)
C4 C1 C2 C3 -0.14(9)
C1 C2 C3 O3 116.17(10)
C12 C2 C3 O3 -63.71(14)
C1 C2 C3 O4 -118.12(10)
C12 C2 C3 O4 61.99(15)
C1 C2 C3 C4 0.13(9)
C12 C2 C3 C4 -179.76(11)
C2 C1 C4 O5 179.40(17)
C5 C1 C4 O5 2.8(3)
C2 C1 C4 C3 0.13(9)
C5 C1 C4 C3 -176.46(13)
O3 C3 C4 O5 69.18(19)
O4 C3 C4 O5 -61.9(2)
C2 C3 C4 O5 -179.41(17)
O3 C3 C4 C1 -111.53(10)
O4 C3 C4 C1 117.38(10)
C2 C3 C4 C1 -0.12(8)
C2 C1 C5 O2 -22.3(2)
C4 C1 C5 O2 152.96(14)
C2 C1 C5 O1 159.92(13)
C4 C1 C5 O1 -24.83(17)
C11 C6 C7 C8 1.46(18)
O1 C6 C7 C8 -174.58(10)
C6 C7 C8 C9 -0.19(19)
C7 C8 C9 C10 -1.25(19)
C8 C9 C10 C11 1.46(19)
C7 C6 C11 C10 -1.25(18)
O1 C6 C11 C10 174.71(10)
C9 C10 C11 C6 -0.23(18)
C1 C2 C12 C13 5.2(2)
C3 C2 C12 C13 -174.95(10)
C1 C2 C12 C17 -175.00(13)
C3 C2 C12 C17 4.83(16)
C17 C12 C13 C14 -0.11(16)
C2 C12 C13 C14 179.67(11)
C12 C13 C14 C15 0.06(18)
C13 C14 C15 C16 0.22(18)
C14 C15 C16 C17 -0.44(18)
C15 C16 C17 C12 0.39(17)
C13 C12 C17 C16 -0.11(16)
C2 C12 C17 C16 -179.90(10)
O2 C5 O1 C6 2.98(18)
C1 C5 O1 C6 -179.17(9)
C7 C6 O1 C5 -108.96(12)
C11 C6 O1 C5 74.90(13)
O4 C3 O3 C18 64.20(13)
C2 C3 O3 C18 -165.38(11)
C4 C3 O3 C18 -71.24(13)
O3 C3 O4 C19 -174.22(11)
C2 C3 O4 C19 58.31(14)
C4 C3 O4 C19 -39.52(14)
