#------------------------------------------------------------------------------
#$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $
#$Revision: 91932 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/21/1502107.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_1502107
loop_
_publ_author_name
'Egan, Ben A.'
'Paradowski, Michael'
'Thomas, Lynne H.'
'Marquez, Rodolfo'
_publ_contact_author             'Rodolfo Marquez '
_publ_section_title
;
 Regiocontrolled rearrangement of isobenzofurans.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2086
_journal_page_last               2089
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-01-10T13:49:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.500(3)
_cell_length_b                   15.178(3)
_cell_length_c                   11.351(2)
_cell_measurement_reflns_used    17520
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1
_cell_volume                     2325.9(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28327
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.9036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                2086
_reflns_number_total             2670
_reflns_threshold_expression     >2\s(I)
_[local]_cod_data_source_file    ol200498k_si_003.cif
_[local]_cod_data_source_block   beo32a_2
_[local]_cod_cif_authors_sg_H-M  Pbcn
_cod_original_cell_volume        2325.7(8)
_cod_database_code               1502107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
H8 0.0622(11) 0.3206(9) 0.3662(12) 0.020(4) Uiso d 1 H
H7 0.1109(11) 0.3569(9) 0.1822(12) 0.017(3) Uiso d 1 H
H9 0.2418(11) 0.4189(9) 0.3963(12) 0.017(3) Uiso d 1 H
H1 0.0651(11) 0.1010(9) -0.0395(14) 0.025(4) Uiso d 1 H
H4 -0.0077(13) 0.2258(9) -0.1212(13) 0.028(4) Uiso d 1 H
H5 0.1090(13) 0.2157(11) -0.1605(14) 0.034(4) Uiso d 1 H
H11 0.0455(12) 0.4844(10) 0.3494(13) 0.032(4) Uiso d 1 H
H14 0.0723(12) 0.4145(10) 0.5526(13) 0.029(4) Uiso d 1 H
H6 0.0557(12) 0.3135(11) -0.1598(14) 0.031(4) Uiso d 1 H
H15 0.1796(12) 0.3692(11) 0.5828(14) 0.032(4) Uiso d 1 H
H3 0.1388(11) 0.0190(10) 0.2911(13) 0.026(4) Uiso d 1 H
H2 0.0934(11) -0.0144(11) 0.0975(13) 0.030(4) Uiso d 1 H
H16 0.2643(14) 0.3463(12) 0.1219(18) 0.048(5) Uiso d 1 H
H12 0.1382(11) 0.5480(11) 0.3839(14) 0.030(4) Uiso d 1 H
H13 0.1696(12) 0.4747(11) 0.5715(14) 0.033(4) Uiso d 1 H
H10 0.1391(11) 0.4967(10) 0.2603(15) 0.030(4) Uiso d 1 H
O2 0.25704(7) 0.33778(6) 0.19992(8) 0.0226(2) Uani d 1 O
O4 0.19894(7) 0.11756(6) 0.46162(8) 0.0252(2) Uani d 1 O
O3 0.18368(7) 0.25855(6) 0.42339(7) 0.0213(2) Uani d 1 O
O1 0.08986(7) 0.27271(6) -0.00126(8) 0.0237(2) Uani d 1 O
C3 0.14447(9) 0.15441(9) 0.26797(11) 0.0200(3) Uani d 1 C
C4 0.13234(9) 0.22284(9) 0.18743(11) 0.0191(3) Uani d 1 C
C8 0.15593(10) 0.31641(8) 0.22333(11) 0.0186(3) Uani d 1 C
C6 0.08613(10) 0.11483(9) 0.04009(12) 0.0232(3) Uani d 1 C
C5 0.10184(10) 0.20224(9) 0.07226(11) 0.0205(3) Uani d 1 C
C13 0.17667(9) 0.17418(9) 0.39033(11) 0.0201(3) Uani d 1 C
C12 0.14653(12) 0.41782(10) 0.53932(12) 0.0252(3) Uani d 1 C
C1 0.10148(10) 0.04764(10) 0.12138(13) 0.0247(3) Uani d 1 C
C10 0.16922(10) 0.41444(9) 0.40761(11) 0.0198(3) Uani d 1 C
C2 0.12985(10) 0.06659(9) 0.23561(13) 0.0231(3) Uani d 1 C
C9 0.13539(9) 0.32770(8) 0.35397(11) 0.0186(3) Uani d 1 C
C11 0.11926(11) 0.49153(10) 0.34543(13) 0.0259(3) Uani d 1 C
C7 0.05992(12) 0.25447(11) -0.12018(12) 0.0283(3) Uani d 1 C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0213(5) 0.0299(5) 0.0166(5) -0.0036(4) 0.0017(4) -0.0002(4)
O4 0.0315(5) 0.0240(5) 0.0202(5) -0.0001(4) -0.0017(4) 0.0038(4)
O3 0.0260(5) 0.0206(5) 0.0172(4) 0.0017(4) -0.0020(4) 0.0003(4)
O1 0.0281(5) 0.0282(5) 0.0147(4) 0.0027(4) -0.0044(4) -0.0024(4)
C3 0.0162(6) 0.0249(7) 0.0188(6) 0.0003(5) 0.0022(5) -0.0015(5)
C4 0.0152(6) 0.0240(7) 0.0183(6) 0.0018(5) 0.0013(5) -0.0025(5)
C8 0.0171(6) 0.0224(7) 0.0165(6) 0.0012(5) -0.0012(5) -0.0008(5)
C6 0.0183(6) 0.0309(7) 0.0204(7) -0.0010(6) 0.0008(5) -0.0081(6)
C5 0.0164(6) 0.0270(7) 0.0180(6) 0.0016(5) 0.0008(5) -0.0020(5)
C13 0.0175(6) 0.0232(7) 0.0195(6) -0.0005(5) 0.0030(5) -0.0003(5)
C12 0.0295(8) 0.0283(7) 0.0178(6) -0.0001(6) 0.0002(6) -0.0045(6)
C1 0.0212(7) 0.0236(7) 0.0293(7) -0.0027(6) 0.0028(6) -0.0068(6)
C10 0.0199(6) 0.0224(7) 0.0171(6) 0.0003(5) -0.0009(5) -0.0025(5)
C2 0.0206(7) 0.0240(7) 0.0247(7) -0.0011(6) 0.0025(6) -0.0006(6)
C9 0.0174(6) 0.0215(6) 0.0169(6) 0.0022(5) -0.0010(5) 0.0004(5)
C11 0.0303(8) 0.0225(7) 0.0250(7) 0.0017(6) -0.0047(6) -0.0009(6)
C7 0.0316(8) 0.0366(9) 0.0166(7) 0.0024(7) -0.0065(6) -0.0050(6)
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
C13 O3 C9 120.22(10)
C5 O1 C7 117.16(11)
C4 C3 C2 121.48(12)
C4 C3 C13 119.81(12)
C2 C3 C13 118.68(12)
C3 C4 C5 118.60(12)
C3 C4 C8 119.92(11)
C5 C4 C8 121.43(12)
O2 C8 C4 111.39(10)
O2 C8 C9 109.31(10)
C4 C8 C9 109.32(11)
C1 C6 C5 120.14(13)
O1 C5 C6 124.60(12)
O1 C5 C4 115.37(12)
C6 C5 C4 120.03(13)
O4 C13 O3 118.14(12)
O4 C13 C3 123.41(12)
O3 C13 C3 118.44(11)
C2 C1 C6 120.73(13)
C9 C10 C11 110.27(11)
C9 C10 C12 111.15(11)
C11 C10 C12 109.81(11)
C1 C2 C3 118.98(13)
O3 C9 C8 111.29(10)
O3 C9 C10 105.74(10)
C8 C9 C10 115.72(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C8 1.4279(16)
O4 C13 1.2181(16)
O3 C13 1.3377(16)
O3 C9 1.4653(15)
O1 C5 1.3663(16)
O1 C7 1.4360(16)
C3 C4 1.3933(18)
C3 C2 1.3967(18)
C3 C13 1.4859(18)
C4 C5 1.4058(18)
C4 C8 1.5114(18)
C8 C9 1.5182(18)
C6 C1 1.391(2)
C6 C5 1.3922(19)
C12 C10 1.5269(18)
C1 C2 1.382(2)
C10 C9 1.5207(18)
C10 C11 1.5239(19)
_journal_paper_doi 10.1021/ol200498k