#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:22:33 +0100 (dom 24 de nov de 2019) $
#$Revision: 238325 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/51/1555105.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_1555105
loop_
_publ_author_name
'Rashid, Showkat'
'Bhat, Bilal A.'
'Mehta, Goverdhan'
_publ_section_title
;
 Regenerative γ-Lactone Annulations: A Modular, Iterative Approach to
 Oligo-tetrahydrofuran Molecular Stairs and Related Frameworks.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3604
_journal_page_last               3607
_journal_paper_doi               10.1021/acs.orglett.5b01707
_journal_volume                  17
_journal_year                    2015
_chemical_compound_source        'see text'
_chemical_formula_iupac          'C8 H10 O4'
_chemical_formula_moiety         'C8 H10 O4'
_chemical_formula_structural     'C8 H10 O4'
_chemical_formula_sum            'C8 H10 O4'
_chemical_formula_weight         170.16
_chemical_name_systematic
(3aR,3bR,6aS,7aR)-hexahydrodifuro[2,3-b:3',2'-d]furan-2(3H)-one
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.571(6)
_cell_length_b                   5.838(3)
_cell_length_c                   12.338(7)
_cell_measurement_reflns_used    2586
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      3.30
_cell_volume                     761.4(7)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'PLATON (Spek, 2003) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4994
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'see text'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         733
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0580
_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)+(0.0950P)²+0.1423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1440
_reflns_number_gt                661
_reflns_number_total             733
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol5b01707_si_002.cif
_cod_data_source_block           compound_16
_cod_database_code               1555105
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-x,y,1/2+z
4 1/2+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
O4 O 0.0810(3) 0.3247(6) 0.9817(3) 0.0536(9) Uani 1 1 d .
O2 O -0.1544(3) 0.4642(6) 0.7044(3) 0.0560(9) Uani 1 1 d .
O1 O -0.2687(3) 0.2284(7) 0.6014(4) 0.0780(12) Uani 1 1 d .
O3 O -0.0151(3) 0.5291(6) 0.8449(3) 0.0531(9) Uani 1 1 d .
C5 C -0.0055(4) 0.3125(8) 0.8989(4) 0.0427(10) Uani 1 1 d .
H5 H -0.0882 0.2642 0.9264 0.051 Uiso 1 1 calc R
C2 C -0.0393(4) 0.1787(9) 0.6163(4) 0.0498(11) Uani 1 1 d .
H2A H -0.0435 0.0131 0.6211 0.060 Uiso 1 1 calc R
H2B H -0.0076 0.2215 0.5454 0.060 Uiso 1 1 calc R
C7 C 0.1754(4) 0.0811(10) 0.8566(4) 0.0599(13) Uani 1 1 d .
H7A H 0.1749 -0.0672 0.8920 0.072 Uiso 1 1 calc R
H7B H 0.2374 0.0795 0.7987 0.072 Uiso 1 1 calc R
C1 C -0.1665(4) 0.2852(9) 0.6377(4) 0.0527(12) Uani 1 1 d .
C3 C 0.0419(4) 0.2766(7) 0.7048(4) 0.0425(10) Uani 1 1 d .
H3 H 0.1282 0.3038 0.6788 0.051 Uiso 1 1 calc R
C4 C -0.0221(4) 0.5000(9) 0.7348(4) 0.0483(11) Uani 1 1 d .
H4 H 0.0150 0.6299 0.6958 0.058 Uiso 1 1 calc R
C6 C 0.0433(4) 0.1425(7) 0.8132(4) 0.0408(10) Uani 1 1 d .
H6 H -0.0110 0.0066 0.8092 0.049 Uiso 1 1 calc R
C8 C 0.2024(5) 0.2702(10) 0.9364(4) 0.0626(14) Uani 1 1 d .
H8A H 0.2604 0.2185 0.9923 0.075 Uiso 1 1 calc R
H8B H 0.2387 0.4022 0.9002 0.075 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
O4 0.0476(17) 0.071(2) 0.0420(16) -0.0051(17) -0.0007(15) 0.0012(15)
O2 0.0468(17) 0.070(2) 0.0512(18) -0.0046(19) -0.0017(15) 0.0223(15)
O1 0.045(2) 0.119(3) 0.070(3) -0.006(3) -0.0164(18) 0.004(2)
O3 0.059(2) 0.0504(18) 0.0499(18) -0.0060(16) -0.0011(16) 0.0071(14)
C5 0.030(2) 0.052(3) 0.046(2) -0.004(2) 0.0054(18) -0.0029(17)
C2 0.043(2) 0.061(3) 0.045(3) -0.002(2) -0.001(2) 0.011(2)
C7 0.044(3) 0.084(3) 0.052(3) 0.008(3) -0.004(2) 0.020(2)
C1 0.042(3) 0.072(3) 0.044(3) 0.003(2) -0.004(2) 0.006(2)
C3 0.031(2) 0.050(2) 0.046(2) -0.005(2) 0.0033(19) 0.0007(17)
C4 0.044(3) 0.049(2) 0.052(3) -0.001(2) 0.002(2) 0.0016(19)
C6 0.0323(19) 0.047(2) 0.043(2) -0.0010(18) -0.0005(17) -0.0009(16)
C8 0.033(2) 0.098(4) 0.057(3) -0.003(3) -0.006(2) -0.005(2)
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 O4 C8 107.1(4)
C1 O2 C4 111.2(3)
C4 O3 C5 110.8(4)
O4 C5 O3 110.3(4)
O4 C5 C6 108.8(3)
O3 C5 C6 105.9(4)
O4 C5 H5 110.6
O3 C5 H5 110.6
C6 C5 H5 110.6
C3 C2 C1 103.1(4)
C3 C2 H2A 111.1
C1 C2 H2A 111.1
C3 C2 H2B 111.1
C1 C2 H2B 111.1
H2A C2 H2B 109.1
C8 C7 C6 103.3(4)
C8 C7 H7A 111.1
C6 C7 H7A 111.1
C8 C7 H7B 111.1
C6 C7 H7B 111.1
H7A C7 H7B 109.1
O1 C1 O2 121.7(4)
O1 C1 C2 128.1(5)
O2 C1 C2 110.2(4)
C2 C3 C4 104.4(4)
C2 C3 C6 116.1(4)
C4 C3 C6 103.2(4)
C2 C3 H3 110.9
C4 C3 H3 110.9
C6 C3 H3 110.9
O3 C4 O2 108.9(4)
O3 C4 C3 108.9(4)
O2 C4 C3 104.0(4)
O3 C4 H4 111.6
O2 C4 H4 111.6
C3 C4 H4 111.6
C7 C6 C5 102.4(4)
C7 C6 C3 115.2(4)
C5 C6 C3 105.3(3)
C7 C6 H6 111.1
C5 C6 H6 111.1
C3 C6 H6 111.1
O4 C8 C7 104.3(4)
O4 C8 H8A 110.9
C7 C8 H8A 110.9
O4 C8 H8B 110.9
C7 C8 H8B 110.9
H8A C8 H8B 108.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C5 1.374(6)
O4 C8 1.436(6)
O2 C1 1.336(6)
O2 C4 1.463(6)
O1 C1 1.216(6)
O3 C4 1.372(6)
O3 C5 1.433(6)
C5 C6 1.539(6)
C5 H5 0.9800
C2 C3 1.502(6)
C2 C1 1.504(7)
C2 H2A 0.9700
C2 H2B 0.9700
C7 C8 1.507(8)
C7 C6 1.537(6)
C7 H7A 0.9700
C7 H7B 0.9700
C3 C4 1.515(6)
C3 C6 1.549(6)
C3 H3 0.9800
C4 H4 0.9800
C6 H6 0.9800
C8 H8A 0.9700
C8 H8B 0.9700
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
C8 O4 C5 O3 -88.5(4)
C8 O4 C5 C6 27.3(5)
C4 O3 C5 O4 138.5(4)
C4 O3 C5 C6 21.0(5)
C4 O2 C1 O1 -178.8(5)
C4 O2 C1 C2 0.3(5)
C3 C2 C1 O1 -164.9(5)
C3 C2 C1 O2 16.1(5)
C1 C2 C3 C4 -25.1(5)
C1 C2 C3 C6 87.8(5)
C5 O3 C4 O2 86.5(5)
C5 O3 C4 C3 -26.3(5)
C1 O2 C4 O3 -132.5(4)
C1 O2 C4 C3 -16.5(5)
C2 C3 C4 O3 141.6(4)
C6 C3 C4 O3 19.7(5)
C2 C3 C4 O2 25.6(5)
C6 C3 C4 O2 -96.2(4)
C8 C7 C6 C5 -17.3(5)
C8 C7 C6 C3 96.4(4)
O4 C5 C6 C7 -5.2(5)
O3 C5 C6 C7 113.4(4)
O4 C5 C6 C3 -126.1(4)
O3 C5 C6 C3 -7.5(4)
C2 C3 C6 C7 127.6(4)
C4 C3 C6 C7 -118.8(4)
C2 C3 C6 C5 -120.3(4)
C4 C3 C6 C5 -6.7(4)
C5 O4 C8 C7 -38.6(5)
C6 C7 C8 O4 33.7(5)
