#------------------------------------------------------------------------------
#$Date: 2018-08-16 04:37:48 +0300 (Thu, 16 Aug 2018) $
#$Revision: 209775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/35/7113510.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_7113510
loop_
_publ_author_name
'Grigg, Ronald'
'Zhang, Lixin'
'Collard, Simon'
'Keep, Ann'
_publ_section_title
;
 Palladium catalysed [2 + 2 + 1] intramolecular cycloaddition for the
 preparation of bicyclo[3.3.0]octa-1.5-dien-3-ones from 1,6-diynes
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   15
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1902
_journal_page_last               1903
_journal_paper_doi               10.1039/b302841k
_journal_year                    2003
_chemical_formula_sum            'C12 H12 O5'
_chemical_formula_weight         236.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                77.7220(13)
_cell_angle_beta                 75.5740(13)
_cell_angle_gamma                82.5810(19)
_cell_formula_units_Z            2
_cell_length_a                   5.70010(10)
_cell_length_b                   9.0939(3)
_cell_length_c                   11.3003(4)
_cell_measurement_temperature    150(2)
_cell_volume                     552.52(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection
'DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)'
_computing_data_reduction
'DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)'
_computing_molecular_graphics    ORTEX
_computing_publication_material  'WinCIF (Thornton-Pett, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Nonius KappaCCD area-detector diffractometer'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_detector       'CCD plate'
_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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        'not measured'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
?
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.09
_refine_ls_extinction_coef       0.10(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     Shelxl
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.23
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0726P)²+0.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1760
_reflns_number_total             2146
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7103804
_cod_data_source_file            b302841k.txt
_cod_data_source_block           z122
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7113510
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
C1 C 0.1782(4) 0.7234(2) 0.20137(19) 0.0236(5) Uani 1 1 d
C2 C 0.3168(4) 0.8052(2) 0.07620(19) 0.0251(5) Uani 1 1 d
H2 H 0.468(5) 0.849(3) 0.070(2) 0.028(6) Uiso 1 1 d
C3 C 0.2121(4) 0.7948(2) -0.0152(2) 0.0248(5) Uani 1 1 d
C4 C -0.0058(4) 0.7131(2) 0.0342(2) 0.0252(5) Uani 1 1 d
C5 C -0.0562(4) 0.6802(3) 0.1735(2) 0.0255(5) Uani 1 1 d
H5A H -0.193(5) 0.741(3) 0.209(3) 0.040(7) Uiso 1 1 d
H5B H -0.088(4) 0.576(3) 0.209(2) 0.029(6) Uiso 1 1 d
C6 C 0.2582(4) 0.8293(3) -0.1537(2) 0.0293(5) Uani 1 1 d
H5 H 0.244(5) 0.939(3) -0.193(3) 0.041(7) Uiso 1 1 d
H6 H 0.417(5) 0.790(3) -0.195(2) 0.037(7) Uiso 1 1 d
C7 C 0.0557(4) 0.7512(2) -0.1778(2) 0.0293(5) Uani 1 1 d
C8 C -0.0987(4) 0.6865(3) -0.0569(2) 0.0281(5) Uani 1 1 d
H8 H -0.235(6) 0.634(4) -0.048(3) 0.051(8) Uiso 1 1 d
C9 C 0.3230(4) 0.5770(2) 0.24660(19) 0.0237(5) Uani 1 1 d
C10 C 0.3547(5) 0.3888(3) 0.4235(2) 0.0367(6) Uani 1 1 d
H10B H 0.303(5) 0.378(3) 0.509(3) 0.047(8) Uiso 1 1 d
H10A H 0.289(6) 0.300(4) 0.402(3) 0.056(9) Uiso 1 1 d
H10C H 0.530(6) 0.377(4) 0.403(3) 0.058(9) Uiso 1 1 d
C11 C 0.1259(4) 0.8227(2) 0.29959(19) 0.0236(5) Uani 1 1 d
C12 C 0.3137(4) 0.9428(3) 0.4137(2) 0.0298(5) Uani 1 1 d
H12C H 0.228(5) 0.889(3) 0.495(3) 0.036(7) Uiso 1 1 d
H12B H 0.479(5) 0.960(3) 0.414(2) 0.035(7) Uiso 1 1 d
H12A H 0.217(5) 1.038(3) 0.394(3) 0.037(7) Uiso 1 1 d
O1 O 0.0319(3) 0.7432(2) -0.28094(15) 0.0400(5) Uani 1 1 d
O2 O 0.2479(3) 0.53316(17) 0.36940(14) 0.0314(4) Uani 1 1 d
O3 O 0.4746(3) 0.50812(17) 0.17970(15) 0.0319(4) Uani 1 1 d
O4 O 0.3354(3) 0.85639(17) 0.31650(14) 0.0280(4) Uani 1 1 d
O5 O -0.0726(3) 0.86641(17) 0.35330(14) 0.0295(4) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 C11 111.22(17)
C2 C1 C9 110.70(16)
C11 C1 C9 108.95(16)
C2 C1 C5 104.43(16)
C11 C1 C5 113.39(17)
C9 C1 C5 108.05(16)
C3 C2 C1 110.76(18)
C3 C2 H2 128.7(14)
C1 C2 H2 120.4(14)
C2 C3 C4 110.86(19)
C2 C3 C6 140.0(2)
C4 C3 C6 108.91(18)
C8 C4 C3 111.87(19)
C8 C4 C5 138.8(2)
C3 C4 C5 109.35(17)
C4 C5 C1 103.37(17)
C4 C5 H5A 111.7(17)
C1 C5 H5A 109.7(16)
C4 C5 H5B 113.2(15)
C1 C5 H5B 112.0(14)
H5A C5 H5B 107(2)
C3 C6 C7 102.09(18)
C3 C6 H5 116.1(16)
C7 C6 H5 108.5(16)
C3 C6 H6 114.0(15)
C7 C6 H6 110.8(16)
H5 C6 H6 105(2)
O1 C7 C8 126.5(2)
O1 C7 C6 124.8(2)
C8 C7 C6 108.64(18)
C4 C8 C7 108.37(19)
C4 C8 H8 127.6(19)
C7 C8 H8 124.0(19)
O3 C9 O2 125.01(19)
O3 C9 C1 124.54(19)
O2 C9 C1 110.37(17)
O2 C10 H10B 107.7(19)
O2 C10 H10A 111.7(17)
H10B C10 H10A 105(3)
O2 C10 H10C 115(2)
H10B C10 H10C 108(3)
H10A C10 H10C 109(3)
O5 C11 O4 124.59(19)
O5 C11 C1 125.79(18)
O4 C11 C1 109.62(17)
O4 C12 H12C 111.0(16)
O4 C12 H12B 106.6(15)
H12C C12 H12B 112(2)
O4 C12 H12A 108.9(15)
H12C C12 H12A 107(2)
H12B C12 H12A 112(2)
C9 O2 C10 116.29(18)
C11 O4 C12 115.71(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.525(3)
C1 C11 1.526(3)
C1 C9 1.533(3)
C1 C5 1.561(3)
C2 C3 1.340(3)
C2 H2 0.98(3)
C3 C4 1.457(3)
C3 C6 1.491(3)
C4 C8 1.346(3)
C4 C5 1.498(3)
C5 H5A 0.95(3)
C5 H5B 0.97(3)
C6 C7 1.536(3)
C6 H5 1.00(3)
C6 H6 0.97(3)
C7 O1 1.225(3)
C7 C8 1.476(3)
C8 H8 0.94(3)
C9 O3 1.203(3)
C9 O2 1.334(3)
C10 O2 1.451(3)
C10 H10B 0.93(3)
C10 H10A 1.03(3)
C10 H10C 0.96(3)
C11 O5 1.204(3)
C11 O4 1.337(2)
C12 O4 1.454(3)
C12 H12C 0.98(3)
C12 H12B 0.98(3)
C12 H12A 0.98(3)
