#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/61/1506177.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_1506177
loop_
_publ_author_name
'Leyhane, Andrew J.'
'Snapper, Marc L.'
_publ_section_title
;
 Functionalized oxepines via fragmentation of highly strained epoxides.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5183
_journal_page_last               5186
_journal_paper_doi               10.1021/ol061682j
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C10 H12 O4'
_chemical_formula_weight         196.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.640(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0680(6)
_cell_length_b                   10.6903(10)
_cell_length_c                   14.2193(14)
_cell_measurement_reflns_used    2426
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.87
_cell_volume                     921.41(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6682
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0472
_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)+(0.0839P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                1793
_reflns_number_total             2283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061682jsi20060708_025720.cif
_cod_data_source_block           ajl01t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506177
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O2 O 0.23298(17) 0.47440(9) 0.40738(7) 0.0345(3) Uani 1 1 d .
O1 O 0.58205(18) 0.80755(9) 0.30347(8) 0.0387(3) Uani 1 1 d .
O4 O -0.15148(16) 0.61423(11) 0.10817(7) 0.0350(3) Uani 1 1 d .
C7 C 0.3525(2) 0.58889(13) 0.42288(9) 0.0290(3) Uani 1 1 d .
H7A H 0.5130 0.5730 0.4309 0.035 Uiso 1 1 calc R
H7B H 0.3024 0.6330 0.4793 0.035 Uiso 1 1 calc R
C3 C 0.3964(2) 0.63272(12) 0.23614(9) 0.0238(3) Uani 1 1 d .
H3A H 0.5272 0.5760 0.2344 0.029 Uiso 1 1 calc R
C6 C 0.2993(2) 0.66333(12) 0.33512(9) 0.0234(3) Uani 1 1 d .
C9 C 0.0689(2) 0.61754(13) 0.29767(9) 0.0268(3) Uani 1 1 d .
H9A H -0.0479 0.6835 0.2929 0.032 Uiso 1 1 calc R
C2 C 0.1693(2) 0.58099(11) 0.20330(9) 0.0234(3) Uani 1 1 d .
H2A H 0.1788 0.4877 0.1997 0.028 Uiso 1 1 calc R
O3 O 0.16571(18) 0.67294(12) 0.04946(8) 0.0515(4) Uani 1 1 d .
C1 C 0.0654(2) 0.62938(12) 0.11235(9) 0.0258(3) Uani 1 1 d .
C5 C 0.3499(2) 0.79944(12) 0.31959(10) 0.0317(3) Uani 1 1 d .
H5A H 0.2527 0.8712 0.3355 0.038 Uiso 1 1 calc R
C4 C 0.4327(2) 0.77281(13) 0.22582(10) 0.0301(3) Uani 1 1 d .
H4A H 0.4010 0.8231 0.1675 0.036 Uiso 1 1 calc R
C8 C 0.0236(3) 0.51018(16) 0.36468(11) 0.0384(4) Uani 1 1 d .
H8A H -0.0776 0.5376 0.4133 0.046 Uiso 1 1 calc R
H8B H -0.0447 0.4389 0.3297 0.046 Uiso 1 1 calc R
C10 C -0.2670(3) 0.65649(15) 0.02249(11) 0.0391(4) Uani 1 1 d .
H10A H -0.4254 0.6413 0.0268 0.059 Uiso 1 1 calc R
H10B H -0.2124 0.6106 -0.0314 0.059 Uiso 1 1 calc R
H10C H -0.2411 0.7462 0.0141 0.059 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 0.0033 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
C7 O2 C8 105.61(10)
C5 O1 C4 61.47(9)
C1 O4 C10 116.13(11)
O2 C7 C6 103.69(10)
C4 C3 C2 117.17(10)
C4 C3 C6 86.78(10)
C2 C3 C6 88.82(9)
C7 C6 C5 126.60(11)
C7 C6 C9 105.87(10)
C5 C6 C9 116.18(11)
C7 C6 C3 123.63(11)
C5 C6 C3 89.00(10)
C9 C6 C3 89.76(9)
C8 C9 C2 116.16(12)
C8 C9 C6 102.04(10)
C2 C9 C6 89.60(10)
C1 C2 C3 118.15(11)
C1 C2 C9 119.48(11)
C3 C2 C9 91.66(9)
O3 C1 O4 123.46(12)
O3 C1 C2 124.61(12)
O4 C1 C2 111.88(11)
O1 C5 C4 59.41(9)
O1 C5 C6 106.82(11)
C4 C5 C6 91.52(11)
O1 C4 C5 59.13(9)
O1 C4 C3 105.54(10)
C5 C4 C3 92.63(10)
O2 C8 C9 106.46(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C7 1.4344(17)
O2 C8 1.4347(18)
O1 C5 1.4400(19)
O1 C4 1.4442(16)
O4 C1 1.3248(16)
O4 C10 1.4494(15)
C7 C6 1.5024(17)
C3 C4 1.5219(18)
C3 C2 1.5372(17)
C3 C6 1.5849(18)
C6 C5 1.5055(18)
C6 C9 1.5519(17)
C9 C8 1.525(2)
C9 C2 1.5490(18)
C2 C1 1.5041(17)
O3 C1 1.1987(17)
C5 C4 1.474(2)
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 O2 C7 C6 -40.78(14)
O2 C7 C6 C5 169.19(13)
O2 C7 C6 C9 27.69(14)
O2 C7 C6 C3 -72.91(15)
C4 C3 C6 C7 -136.79(12)
C2 C3 C6 C7 105.92(12)
C4 C3 C6 C5 -1.99(10)
C2 C3 C6 C5 -119.28(10)
C4 C3 C6 C9 114.20(9)
C2 C3 C6 C9 -3.09(9)
C7 C6 C9 C8 -5.30(14)
C5 C6 C9 C8 -151.46(13)
C3 C6 C9 C8 119.77(11)
C7 C6 C9 C2 -122.01(11)
C5 C6 C9 C2 91.83(13)
C3 C6 C9 C2 3.07(9)
C4 C3 C2 C1 42.35(16)
C6 C3 C2 C1 128.12(11)
C4 C3 C2 C9 -82.67(12)
C6 C3 C2 C9 3.10(9)
C8 C9 C2 C1 129.65(12)
C6 C9 C2 C1 -127.11(11)
C8 C9 C2 C3 -106.40(11)
C6 C9 C2 C3 -3.16(9)
C10 O4 C1 O3 -1.4(2)
C10 O4 C1 C2 -179.20(11)
C3 C2 C1 O3 24.6(2)
C9 C2 C1 O3 134.49(15)
C3 C2 C1 O4 -157.62(11)
C9 C2 C1 O4 -47.74(16)
C4 O1 C5 C6 81.57(11)
C7 C6 C5 O1 76.25(17)
C9 C6 C5 O1 -145.60(11)
C3 C6 C5 O1 -56.36(11)
C7 C6 C5 C4 134.66(13)
C9 C6 C5 C4 -87.19(13)
C3 C6 C5 C4 2.05(10)
C5 O1 C4 C3 -83.64(11)
C6 C5 C4 O1 -108.70(10)
O1 C5 C4 C3 106.56(10)
C6 C5 C4 C3 -2.14(10)
C2 C3 C4 O1 147.68(11)
C6 C3 C4 O1 60.67(11)
C2 C3 C4 C5 89.04(13)
C6 C3 C4 C5 2.03(10)
C7 O2 C8 C9 38.09(15)
C2 C9 C8 O2 76.46(14)
C6 C9 C8 O2 -19.09(15)
