#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/31/1513143.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_1513143
loop_
_publ_author_name
'Ngatimin, Marsewi'
'Frey, Raphael'
'Levens, Alison'
'Nakano, Yuji'
'Kowalczyk, Marcin'
'Konstas, Kristina'
'Hutt, Oliver E.'
'Lupton, David W.'
_publ_section_title
;
 Iodobenzene-Catalyzed Oxabicyclo[3.2.1]octane and [4.2.1]Nonane Synthesis
 via Cascade C--O/C--C Formation
;
_journal_issue                   22
_journal_name_full               'Organic Letters'
_journal_page_first              5858
_journal_paper_doi               10.1021/ol4029308
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29
_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                 108.356(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6990(8)
_cell_length_b                   6.3160(3)
_cell_length_c                   15.3815(7)
_cell_measurement_reflns_used    2299
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.4153
_cell_measurement_theta_min      2.3986
_cell_volume                     1263.14(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_molecular_graphics    X-Seed/POVRay
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5565
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0386
_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)+(0.0347P)²+0.4717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                1847
_reflns_number_total             2223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4029308_si_002.cif
_cod_data_source_block           kkhutt1
_cod_original_cell_volume        1263.14(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1513143
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
O1 O 0.32688(8) 0.26762(17) 0.29401(7) 0.0209(3) Uani 1 1 d .
O2 O 0.34842(9) 0.58465(19) 0.57620(7) 0.0283(3) Uani 1 1 d .
O3 O -0.14006(9) 0.5906(2) 0.08873(8) 0.0346(3) Uani 1 1 d .
C1 C 0.34342(12) 0.3483(3) 0.20940(10) 0.0213(4) Uani 1 1 d .
H1 H 0.3785 0.2395 0.1824 0.026 Uiso 1 1 calc R
C2 C 0.24223(12) 0.4139(3) 0.14103(10) 0.0219(4) Uani 1 1 d .
H2A H 0.1988 0.2865 0.1210 0.026 Uiso 1 1 calc R
H2B H 0.2555 0.4747 0.0865 0.026 Uiso 1 1 calc R
C3 C 0.18182(12) 0.5793(3) 0.17961(10) 0.0194(4) Uani 1 1 d .
C4 C 0.25715(11) 0.7325(3) 0.24905(10) 0.0178(4) Uani 1 1 d .
H4A H 0.2736 0.8518 0.2143 0.021 Uiso 1 1 calc R
H4B H 0.2211 0.7919 0.2901 0.021 Uiso 1 1 calc R
C5 C 0.35928(11) 0.6321(3) 0.30884(10) 0.0161(3) Uani 1 1 d .
C6 C 0.42175(12) 0.7839(3) 0.38226(10) 0.0179(4) Uani 1 1 d .
H6A H 0.4236 0.9248 0.3546 0.022 Uiso 1 1 calc R
H6B H 0.4933 0.7316 0.4071 0.022 Uiso 1 1 calc R
C7 C 0.37528(12) 0.8048(3) 0.46023(10) 0.0202(4) Uani 1 1 d .
H7A H 0.4235 0.8858 0.5108 0.024 Uiso 1 1 calc R
H7B H 0.3107 0.8871 0.4380 0.024 Uiso 1 1 calc R
C8 C 0.35247(12) 0.5952(3) 0.49738(10) 0.0193(4) Uani 1 1 d .
C9 C 0.33487(12) 0.4125(3) 0.43839(10) 0.0192(4) Uani 1 1 d .
H9 H 0.3201 0.2791 0.4599 0.023 Uiso 1 1 calc R
C10 C 0.33941(11) 0.4318(2) 0.35294(10) 0.0163(3) Uani 1 1 d .
C11 C 0.41323(12) 0.5367(3) 0.24438(10) 0.0195(4) Uani 1 1 d .
H11A H 0.4133 0.6353 0.1944 0.023 Uiso 1 1 calc R
H11B H 0.4846 0.4927 0.2777 0.023 Uiso 1 1 calc R
C12 C 0.11758(13) 0.7097(3) 0.10052(10) 0.0228(4) Uani 1 1 d .
H12 H 0.1526 0.7939 0.0686 0.027 Uiso 1 1 calc R
C13 C 0.01514(13) 0.7161(3) 0.07190(11) 0.0249(4) Uani 1 1 d .
H13 H -0.0193 0.8042 0.0216 0.030 Uiso 1 1 calc R
C14 C -0.04537(13) 0.5908(3) 0.11608(11) 0.0240(4) Uani 1 1 d .
C15 C 0.01266(13) 0.4671(3) 0.19534(11) 0.0243(4) Uani 1 1 d .
H15 H -0.0239 0.3869 0.2272 0.029 Uiso 1 1 calc R
C16 C 0.11493(12) 0.4620(3) 0.22490(11) 0.0217(4) Uani 1 1 d .
H16 H 0.1478 0.3796 0.2777 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
C10 O1 C1 107.66(12)
O1 C1 C2 110.22(12)
O1 C1 C11 102.26(11)
C2 C1 C11 111.71(14)
C1 C2 C3 113.52(12)
C12 C3 C16 110.92(13)
C12 C3 C2 107.72(12)
C16 C3 C2 108.58(14)
C12 C3 C4 107.81(13)
C16 C3 C4 110.76(12)
C2 C3 C4 111.02(12)
C5 C4 C3 115.52(13)
C10 C5 C6 109.60(12)
C10 C5 C11 98.86(12)
C6 C5 C11 117.00(13)
C10 C5 C4 110.82(12)
C6 C5 C4 111.98(13)
C11 C5 C4 107.83(12)
C5 C6 C7 111.10(12)
C8 C7 C6 114.02(13)
O2 C8 C9 121.73(15)
O2 C8 C7 119.82(14)
C9 C8 C7 118.45(13)
C10 C9 C8 119.66(14)
C9 C10 O1 123.54(14)
C9 C10 C5 126.20(14)
O1 C10 C5 110.26(12)
C1 C11 C5 99.16(12)
C13 C12 C3 124.83(15)
C12 C13 C14 121.56(15)
O3 C14 C15 121.63(16)
O3 C14 C13 122.22(16)
C15 C14 C13 116.15(14)
C16 C15 C14 122.54(16)
C15 C16 C3 123.90(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.3519(18)
O1 C1 1.4800(18)
O2 C8 1.2329(17)
O3 C14 1.2313(19)
C1 C2 1.510(2)
C1 C11 1.515(2)
C2 C3 1.561(2)
C3 C12 1.503(2)
C3 C16 1.509(2)
C3 C4 1.564(2)
C4 C5 1.548(2)
C5 C10 1.500(2)
C5 C6 1.523(2)
C5 C11 1.534(2)
C6 C7 1.530(2)
C7 C8 1.513(2)
C8 C9 1.440(2)
C9 C10 1.341(2)
C12 C13 1.333(2)
C13 C14 1.459(2)
C14 C15 1.455(2)
C15 C16 1.330(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041691
