#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:55:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178450 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/71/4027153.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_4027153
loop_
_publ_author_name
'Nicole M. Cain'
'Edward R. T. Tiekink'
'Dennis K. Taylor'
_publ_contact_author_address
;
    School of Materials Science and Engineering, 
    Nanyang Technological University,  
    Singapore 639798
;
_publ_contact_author_email
;
Edward.Tiekink@gmail.com
;
_publ_contact_author_fax         ' (65) 6790 9801 '
_publ_contact_author_name        ' Edward RT Tiekink '
_publ_contact_author_phone       ' (65) 6790 6402 '
_publ_section_title
;
 Ozonolysis of Bicyclic 1,2-Dioxines: Initial Scope and Mechanistic
 Insights
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3808
_journal_page_last               3819
_journal_paper_doi               10.1021/jo3001518
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C17 H16 O3'
_chemical_formula_sum            'C17 H16 O3'
_chemical_formula_weight         268.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                95.510(4)
_cell_angle_beta                 90.569(6)
_cell_angle_gamma                100.990(7)
_cell_formula_units_Z            2
_cell_length_a                   5.6262(15)
_cell_length_b                   10.040(3)
_cell_length_c                   12.165(3)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.5
_cell_volume                     671.2(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & Brandenburg (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_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  0.061
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4859
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0528
_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)+(0.0711P)²+0.3303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                2417
_reflns_number_total             2741
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo3001518_si_001.cif
_cod_data_source_block           r34
_cod_database_code               4027153
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
O8 O 0.3147(2) 0.46891(11) 0.33813(9) 0.0211(3) Uani 1 1 d D
H8O H 0.262(4) 0.5334(14) 0.3726(16) 0.032 Uiso 1 1 d D
O12 O 1.13848(19) 0.67613(12) 0.48392(10) 0.0233(3) Uani 1 1 d .
O14 O 0.2931(2) 0.68055(12) 0.21836(10) 0.0259(3) Uani 1 1 d .
C1 C 0.5427(3) 0.39761(15) 0.18535(13) 0.0185(3) Uani 1 1 d .
C2 C 0.3508(3) 0.28800(16) 0.16007(14) 0.0219(4) Uani 1 1 d .
H2 H 0.2058 0.2830 0.2002 0.026 Uiso 1 1 calc R
C3 C 0.3697(3) 0.18615(17) 0.07691(14) 0.0253(4) Uani 1 1 d .
H3 H 0.2381 0.1118 0.0609 0.030 Uiso 1 1 calc R
C4 C 0.5789(3) 0.19204(17) 0.01712(14) 0.0247(4) Uani 1 1 d .
H4 H 0.5910 0.1223 -0.0400 0.030 Uiso 1 1 calc R
C5 C 0.7714(3) 0.30115(18) 0.04141(14) 0.0249(4) Uani 1 1 d .
H5 H 0.9156 0.3058 0.0008 0.030 Uiso 1 1 calc R
C6 C 0.7535(3) 0.40278(17) 0.12446(14) 0.0231(4) Uani 1 1 d .
H6 H 0.8857 0.4769 0.1403 0.028 Uiso 1 1 calc R
C7 C 0.5152(3) 0.51334(16) 0.27269(13) 0.0188(3) Uani 1 1 d .
C9 C 0.7494(3) 0.56332(16) 0.34436(13) 0.0200(3) Uani 1 1 d .
H9A H 0.7865 0.4864 0.3822 0.024 Uiso 1 1 calc R
H9B H 0.8854 0.5927 0.2957 0.024 Uiso 1 1 calc R
C10 C 0.7307(3) 0.68067(16) 0.43025(13) 0.0191(3) Uani 1 1 d .
H10A H 0.6945 0.7579 0.3926 0.023 Uiso 1 1 calc R
H10B H 0.5947 0.6516 0.4791 0.023 Uiso 1 1 calc R
C11 C 0.9613(3) 0.72798(16) 0.49983(13) 0.0188(3) Uani 1 1 d .
C13 C 0.4696(3) 0.62983(16) 0.20860(13) 0.0201(3) Uani 1 1 d .
H13 H 0.5879 0.6643 0.1580 0.024 Uiso 1 1 calc R
C15 C 0.9681(3) 0.84190(15) 0.58960(13) 0.0191(3) Uani 1 1 d .
C16 C 1.1591(3) 0.86911(17) 0.66804(14) 0.0222(4) Uani 1 1 d .
H16 H 1.2803 0.8147 0.6645 0.027 Uiso 1 1 calc R
C17 C 1.1718(3) 0.97525(18) 0.75091(14) 0.0258(4) Uani 1 1 d .
H17 H 1.3002 0.9924 0.8048 0.031 Uiso 1 1 calc R
C18 C 0.9978(3) 1.05670(17) 0.75558(15) 0.0266(4) Uani 1 1 d .
H18 H 1.0087 1.1304 0.8117 0.032 Uiso 1 1 calc R
C19 C 0.8079(3) 1.03011(17) 0.67785(15) 0.0251(4) Uani 1 1 d .
H19 H 0.6887 1.0858 0.6809 0.030 Uiso 1 1 calc R
C20 C 0.7918(3) 0.92265(16) 0.59592(14) 0.0219(4) Uani 1 1 d .
H20 H 0.6599 0.9039 0.5438 0.026 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 O8 H8O 113.2(15)
C2 C1 C6 118.48(15)
C2 C1 C7 120.23(14)
C6 C1 C7 121.18(13)
C3 C2 C1 120.59(15)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 120.55(15)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.37(16)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 120.28(16)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 120.72(15)
C5 C6 H6 119.6
C1 C6 H6 119.6
O8 C7 C13 110.45(13)
O8 C7 C1 109.14(12)
C13 C7 C1 105.69(12)
O8 C7 C9 111.40(13)
C13 C7 C9 108.48(12)
C1 C7 C9 111.53(13)
C10 C9 C7 112.98(13)
C10 C9 H9A 109.0
C7 C9 H9A 109.0
C10 C9 H9B 109.0
C7 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C9 112.24(13)
C11 C10 H10A 109.2
C9 C10 H10A 109.2
C11 C10 H10B 109.2
C9 C10 H10B 109.2
H10A C10 H10B 107.9
O12 C11 C15 120.15(14)
O12 C11 C10 121.59(14)
C15 C11 C10 118.26(13)
O14 C13 C7 123.86(15)
O14 C13 H13 118.1
C7 C13 H13 118.1
C20 C15 C16 119.27(15)
C20 C15 C11 121.81(14)
C16 C15 C11 118.92(14)
C17 C16 C15 120.09(16)
C17 C16 H16 120.0
C15 C16 H16 120.0
C16 C17 C18 120.33(16)
C16 C17 H17 119.8
C18 C17 H17 119.8
C17 C18 C19 119.78(16)
C17 C18 H18 120.1
C19 C18 H18 120.1
C20 C19 C18 120.18(16)
C20 C19 H19 119.9
C18 C19 H19 119.9
C19 C20 C15 120.34(15)
C19 C20 H20 119.8
C15 C20 H20 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C7 1.4138(19)
O8 H8O 0.8401(10)
O12 C11 1.219(2)
O14 C13 1.202(2)
C1 C2 1.395(2)
C1 C6 1.400(2)
C1 C7 1.529(2)
C2 C3 1.388(2)
C2 H2 0.9500
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.393(2)
C4 H4 0.9500
C5 C6 1.384(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C13 1.525(2)
C7 C9 1.546(2)
C9 C10 1.518(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.514(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C15 1.498(2)
C13 H13 0.9500
C15 C20 1.394(2)
C15 C16 1.399(2)
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.388(3)
C17 H17 0.9500
C18 C19 1.389(3)
C18 H18 0.9500
C19 C20 1.386(2)
C19 H19 0.9500
C20 H20 0.9500
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
C6 C1 C2 C3 0.4(2)
C7 C1 C2 C3 176.61(14)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C1 0.1(2)
C2 C1 C6 C5 -0.3(2)
C7 C1 C6 C5 -176.42(14)
C2 C1 C7 O8 17.35(19)
C6 C1 C7 O8 -166.57(14)
C2 C1 C7 C13 -101.44(16)
C6 C1 C7 C13 74.64(17)
C2 C1 C7 C9 140.86(15)
C6 C1 C7 C9 -43.05(19)
O8 C7 C9 C10 -59.18(17)
C13 C7 C9 C10 62.59(17)
C1 C7 C9 C10 178.60(12)
C7 C9 C10 C11 179.84(12)
C9 C10 C11 O12 1.3(2)
C9 C10 C11 C15 -178.96(12)
O8 C7 C13 O14 3.9(2)
C1 C7 C13 O14 121.86(16)
C9 C7 C13 O14 -118.42(16)
O12 C11 C15 C20 166.25(15)
C10 C11 C15 C20 -13.5(2)
O12 C11 C15 C16 -12.7(2)
C10 C11 C15 C16 167.62(14)
C20 C15 C16 C17 0.0(2)
C11 C15 C16 C17 178.99(14)
C15 C16 C17 C18 -1.1(2)
C16 C17 C18 C19 1.1(3)
C17 C18 C19 C20 0.0(3)
C18 C19 C20 C15 -1.1(2)
C16 C15 C20 C19 1.1(2)
C11 C15 C20 C19 -177.83(14)
