#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:24:03 +0100 (dom 24 de nov de 2019) $
#$Revision: 238809 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/55/1555503.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_1555503
loop_
_publ_author_name
'More, Atul A.'
'Ramana, Chepuri V.'
_publ_section_title
;
 Total Synthesis of Integrastatin B Enabled by a Benzofuran Oxidative
 Dearomatization Cascade.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1458
_journal_page_last               1461
_journal_paper_doi               10.1021/acs.orglett.6b00404
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                90.831(6)
_cell_angle_beta                 97.639(6)
_cell_angle_gamma                93.425(6)
_cell_formula_units_Z            2
_cell_length_a                   7.2646(7)
_cell_length_b                   8.0955(8)
_cell_length_c                   8.1840(9)
_cell_measurement_reflns_used    5309
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.78
_cell_measurement_theta_min      2.51
_cell_volume                     476.06(8)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8060
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0373
_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)+(0.0550P)²+0.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                1515
_reflns_number_total             1681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00404_si_003.cif
_cod_data_source_block           int_3_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' 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.

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' 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.

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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      'P-1   '
_cod_database_code               1555503
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
_atom_site_refinement_flags
O1 O -0.33320(13) 0.47785(12) 0.11351(13) 0.0499(3) Uani 1 1 d .
O2 O -0.18364(14) 0.18065(13) 0.02642(14) 0.0558(3) Uani 1 1 d .
H2 H -0.1192 0.1055 0.0049 0.084 Uiso 1 1 calc R
O3 O 0.18051(13) 0.13700(12) 0.14432(14) 0.0531(3) Uani 1 1 d .
C1 C -0.3504(2) 0.63296(18) 0.18028(19) 0.0522(4) Uani 1 1 d .
H1 H -0.4604 0.6875 0.1664 0.063 Uiso 1 1 calc R
C2 C -0.1920(2) 0.69660(17) 0.26717(17) 0.0449(3) Uani 1 1 d .
C3 C -0.1664(2) 0.86288(19) 0.3527(2) 0.0599(4) Uani 1 1 d .
H3A H -0.2810 0.9173 0.3352 0.090 Uiso 1 1 calc R
H3B H -0.0707 0.9286 0.3091 0.090 Uiso 1 1 calc R
H3C H -0.1312 0.8492 0.4688 0.090 Uiso 1 1 calc R
C4 C -0.05660(18) 0.57297(16) 0.25884(15) 0.0396(3) Uani 1 1 d .
C5 C -0.15226(18) 0.44364(17) 0.16236(16) 0.0400(3) Uani 1 1 d .
C6 C -0.07592(18) 0.29902(16) 0.12195(16) 0.0414(3) Uani 1 1 d .
C7 C 0.10903(19) 0.28454(16) 0.18466(17) 0.0420(3) Uani 1 1 d .
C8 C 0.3747(2) 0.1205(2) 0.1934(2) 0.0613(4) Uani 1 1 d .
H8A H 0.4448 0.2106 0.1510 0.092 Uiso 1 1 calc R
H8B H 0.4097 0.0176 0.1504 0.092 Uiso 1 1 calc R
H8C H 0.4001 0.1221 0.3116 0.092 Uiso 1 1 calc R
C9 C 0.20942(19) 0.41173(18) 0.28189(18) 0.0461(4) Uani 1 1 d .
H9 H 0.3335 0.3985 0.3217 0.055 Uiso 1 1 calc R
C10 C 0.13088(19) 0.55698(17) 0.32132(16) 0.0425(3) Uani 1 1 d .
C11 C 0.2452(2) 0.6892(2) 0.4286(2) 0.0577(4) Uani 1 1 d .
H11A H 0.3673 0.6524 0.4623 0.086 Uiso 1 1 calc R
H11B H 0.1860 0.7105 0.5242 0.086 Uiso 1 1 calc R
H11C H 0.2549 0.7890 0.3674 0.086 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0390(5) 0.0476(6) 0.0598(6) -0.0111(5) -0.0045(4) 0.0028(4)
O2 0.0446(6) 0.0454(6) 0.0726(7) -0.0208(5) -0.0060(5) -0.0012(4)
O3 0.0405(6) 0.0428(6) 0.0738(7) -0.0114(5) 0.0009(5) 0.0017(4)
C1 0.0490(8) 0.0466(8) 0.0600(9) -0.0066(7) 0.0024(7) 0.0085(6)
C2 0.0500(8) 0.0406(7) 0.0433(7) -0.0018(6) 0.0050(6) 0.0008(6)
C3 0.0695(11) 0.0449(8) 0.0637(10) -0.0098(7) 0.0040(8) 0.0044(7)
C4 0.0439(7) 0.0385(7) 0.0355(7) 0.0001(5) 0.0049(5) -0.0039(5)
C5 0.0362(7) 0.0421(7) 0.0399(7) -0.0012(5) 0.0012(5) -0.0017(5)
C6 0.0403(7) 0.0396(7) 0.0422(7) -0.0044(6) 0.0019(6) -0.0055(5)
C7 0.0400(7) 0.0388(7) 0.0462(7) -0.0011(6) 0.0042(6) -0.0010(6)
C8 0.0412(8) 0.0531(9) 0.0871(12) -0.0120(8) 0.0003(8) 0.0050(7)
C9 0.0370(7) 0.0477(8) 0.0507(8) -0.0014(6) -0.0020(6) -0.0029(6)
C10 0.0436(7) 0.0422(7) 0.0392(7) -0.0016(5) 0.0010(6) -0.0065(6)
C11 0.0532(9) 0.0537(9) 0.0608(9) -0.0121(7) -0.0050(7) -0.0088(7)
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
C5 O1 C1 104.99(11)
C6 O2 H2 109.5
C7 O3 C8 117.25(11)
C2 C1 O1 112.87(13)
C2 C1 H1 123.6
O1 C1 H1 123.6
C1 C2 C4 105.96(12)
C1 C2 C3 125.38(14)
C4 C2 C3 128.67(13)
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C4 C10 118.63(12)
C5 C4 C2 104.96(12)
C10 C4 C2 136.41(13)
O1 C5 C6 124.02(12)
O1 C5 C4 111.22(12)
C6 C5 C4 124.75(12)
O2 C6 C5 119.52(12)
O2 C6 C7 124.41(13)
C5 C6 C7 116.07(12)
O3 C7 C6 114.66(12)
O3 C7 C9 124.57(12)
C6 C7 C9 120.77(13)
O3 C8 H8A 109.5
O3 C8 H8B 109.5
H8A C8 H8B 109.5
O3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C7 122.56(13)
C10 C9 H9 118.7
C7 C9 H9 118.7
C9 C10 C4 117.22(12)
C9 C10 C11 120.28(13)
C4 C10 C11 122.50(13)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.3680(16)
O1 C1 1.3814(18)
O2 C6 1.3667(16)
O2 H2 0.8200
O3 C7 1.3833(17)
O3 C8 1.4293(17)
C1 C2 1.341(2)
C1 H1 0.9300
C2 C4 1.4515(19)
C2 C3 1.498(2)
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C4 C5 1.3949(18)
C4 C10 1.4039(19)
C5 C6 1.379(2)
C6 C7 1.386(2)
C7 C9 1.399(2)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.389(2)
C9 H9 0.9300
C10 C11 1.5097(19)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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 O1 C1 C2 -0.02(17)
O1 C1 C2 C4 -0.35(17)
O1 C1 C2 C3 179.39(13)
C1 C2 C4 C5 0.57(15)
C3 C2 C4 C5 -179.15(14)
C1 C2 C4 C10 -179.14(15)
C3 C2 C4 C10 1.1(3)
C1 O1 C5 C6 179.92(13)
C1 O1 C5 C4 0.41(15)
C10 C4 C5 O1 179.16(11)
C2 C4 C5 O1 -0.62(15)
C10 C4 C5 C6 -0.3(2)
C2 C4 C5 C6 179.88(12)
O1 C5 C6 O2 0.5(2)
C4 C5 C6 O2 179.93(12)
O1 C5 C6 C7 -178.95(12)
C4 C5 C6 C7 0.5(2)
C8 O3 C7 C6 174.75(13)
C8 O3 C7 C9 -5.9(2)
O2 C6 C7 O3 -0.5(2)
C5 C6 C7 O3 178.93(11)
O2 C6 C7 C9 -179.88(13)
C5 C6 C7 C9 -0.5(2)
O3 C7 C9 C10 -179.00(13)
C6 C7 C9 C10 0.3(2)
C7 C9 C10 C4 -0.2(2)
C7 C9 C10 C11 179.22(13)
C5 C4 C10 C9 0.17(19)
C2 C4 C10 C9 179.85(14)
C5 C4 C10 C11 -179.22(13)
C2 C4 C10 C11 0.5(2)
