#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:28:54 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556163.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_1556163
loop_
_publ_author_name
'Albertshofer, Klaus'
'Tan, Bin'
'Barbas, 3rd, Carlos F'
_publ_section_title
;
 Asymmetric construction of spirocyclopentenebenzofuranone core structures
 via highly selective phosphine-catalyzed [3 + 2] cycloaddition reactions.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2958
_journal_page_last               2961
_journal_paper_doi               10.1021/ol401087a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C13 H12 O5'
_chemical_formula_weight         248.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.224(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0607(5)
_cell_length_b                   12.2714(7)
_cell_length_c                   11.6095(6)
_cell_measurement_reflns_used    4021
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.92
_cell_measurement_theta_min      5.25
_cell_volume                     1148.10(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7240
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         68.12
_diffrn_reflns_theta_min         5.25
_exptl_absorpt_coefficient_mu    0.939
_exptl_absorpt_correction_T_max  0.9119
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.3435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                1757
_reflns_number_total             2035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401087a_si_002.cif
_cod_data_source_block           barabs31
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1556163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.21333(14) -0.11932(9) -0.08046(9) 0.0356(3) Uani 1 1 d .
O2 O 0.33665(15) 0.54128(10) 0.12350(10) 0.0409(3) Uani 1 1 d .
O3 O 0.13490(17) 0.05612(10) -0.08420(11) 0.0497(4) Uani 1 1 d .
O4 O 0.48153(14) 0.19077(9) 0.26510(9) 0.0343(3) Uani 1 1 d .
O5 O 0.52232(15) 0.01028(9) 0.27445(10) 0.0409(3) Uani 1 1 d .
C1 C 0.1038(2) -0.25474(14) -0.21062(15) 0.0413(4) Uani 1 1 d .
H1A H 0.2167 -0.2818 -0.2219 0.062 Uiso 1 1 calc R
H1B H 0.0369 -0.2668 -0.2809 0.062 Uiso 1 1 calc R
H1C H 0.0540 -0.2938 -0.1463 0.062 Uiso 1 1 calc R
C2 C 0.1097(2) -0.13560(14) -0.18413(14) 0.0367(4) Uani 1 1 d .
H2A H 0.1568 -0.0953 -0.2496 0.044 Uiso 1 1 calc R
H2B H -0.0038 -0.1079 -0.1713 0.044 Uiso 1 1 calc R
C3 C 0.21302(19) -0.01726(13) -0.04021(14) 0.0339(4) Uani 1 1 d .
C4 C 0.31742(19) -0.00610(13) 0.06535(14) 0.0336(4) Uani 1 1 d .
H4 H 0.3603 -0.0708 0.0996 0.040 Uiso 1 1 calc R
C5 C 0.35572(18) 0.08905(13) 0.11603(12) 0.0300(4) Uani 1 1 d .
C6 C 0.32531(18) 0.20405(13) 0.09541(12) 0.0300(4) Uani 1 1 d .
C7 C 0.24589(19) 0.26679(14) 0.00987(13) 0.0335(4) Uani 1 1 d .
H7 H 0.1906 0.2321 -0.0533 0.040 Uiso 1 1 calc R
C8 C 0.2480(2) 0.37909(14) 0.01741(13) 0.0341(4) Uani 1 1 d .
H8 H 0.1950 0.4212 -0.0413 0.041 Uiso 1 1 calc R
C9 C 0.32722(19) 0.43157(13) 0.11021(13) 0.0324(4) Uani 1 1 d .
C10 C 0.2696(2) 0.60762(16) 0.03208(16) 0.0446(4) Uani 1 1 d .
H10A H 0.3226 0.5884 -0.0403 0.067 Uiso 1 1 calc R
H10B H 0.2905 0.6846 0.0496 0.067 Uiso 1 1 calc R
H10C H 0.1497 0.5952 0.0245 0.067 Uiso 1 1 calc R
C11 C 0.46104(18) 0.08603(13) 0.22491(13) 0.0317(4) Uani 1 1 d .
C12 C 0.40252(18) 0.26044(13) 0.18633(12) 0.0306(4) Uani 1 1 d .
C13 C 0.40624(19) 0.37107(13) 0.19822(13) 0.0333(4) Uani 1 1 d .
H13 H 0.4594 0.4053 0.2625 0.040 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 0.0181 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
C3 O1 C2 114.20(12)
C9 O2 C10 117.37(13)
C11 O4 C12 107.47(11)
O1 C2 C1 108.52(13)
O3 C3 O1 123.80(15)
O3 C3 C4 124.39(15)
O1 C3 C4 111.80(13)
C5 C4 C3 124.50(15)
C4 C5 C6 137.57(14)
C4 C5 C11 117.83(14)
C6 C5 C11 104.61(13)
C12 C6 C7 116.93(15)
C12 C6 C5 106.62(13)
C7 C6 C5 136.42(14)
C8 C7 C6 119.91(14)
C7 C8 C9 120.91(14)
O2 C9 C8 124.63(14)
O2 C9 C13 114.72(14)
C8 C9 C13 120.64(15)
O5 C11 O4 121.21(14)
O5 C11 C5 129.97(15)
O4 C11 C5 108.82(12)
C13 C12 O4 122.30(13)
C13 C12 C6 125.27(14)
O4 C12 C6 112.41(14)
C12 C13 C9 116.33(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.337(2)
O1 C2 1.4640(18)
O2 C9 1.357(2)
O2 C10 1.434(2)
O3 C3 1.206(2)
O4 C11 1.3762(19)
O4 C12 1.3956(18)
O5 C11 1.1944(19)
C1 C2 1.494(2)
C3 C4 1.478(2)
C4 C5 1.341(2)
C5 C6 1.451(2)
C5 C11 1.508(2)
C6 C12 1.397(2)
C6 C7 1.401(2)
C7 C8 1.381(2)
C8 C9 1.398(2)
C9 C13 1.405(2)
C12 C13 1.365(2)
