#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028727.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_4028727
loop_
_publ_author_name
'G. Hari Mangeswara Rao'
'Faiz Ahmed Khan'
_publ_section_title
;
 An Unusual Fragmentation of Oxetane-Embedded Tetracyclic Ketal Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11092
_journal_page_last               11095
_journal_paper_doi               10.1021/jo401870s
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H21 Cl O6'
_chemical_formula_sum            'C14 H21 Cl O6'
_chemical_formula_weight         320.76
_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                80.767(3)
_cell_angle_beta                 80.035(3)
_cell_angle_gamma                84.869(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5473(13)
_cell_length_b                   8.2391(14)
_cell_length_c                   12.532(2)
_cell_measurement_reflns_used    3570
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.51
_cell_volume                     756.1(2)
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker smart Apex'
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5016
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0575
_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)+(0.0526P)²+2.4718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                2979
_reflns_number_total             3570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401870s_si_003.cif
_cod_data_source_block           Compound_3g
_cod_database_code               4028727
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
C01 C 0.3287(4) 0.3535(4) 0.2168(3) 0.0169(6) Uani 1 1 d .
H01 H 0.2983 0.4237 0.1508 0.020 Uiso 1 1 calc R
C02 C 0.2261(4) 0.1950(4) 0.2385(3) 0.0204(7) Uani 1 1 d .
H02 H 0.1992 0.1651 0.1707 0.025 Uiso 1 1 calc R
C03 C 0.3500(5) 0.0617(4) 0.2949(3) 0.0200(7) Uani 1 1 d .
H03A H 0.3643 -0.0357 0.2590 0.024 Uiso 1 1 calc R
H03B H 0.2982 0.0308 0.3711 0.024 Uiso 1 1 calc R
C04 C 0.5352(4) 0.1349(4) 0.2864(3) 0.0185(6) Uani 1 1 d .
C05 C 0.5636(4) 0.1781(4) 0.3972(3) 0.0187(7) Uani 1 1 d .
C06 C 0.4367(5) 0.3045(4) 0.4529(3) 0.0213(7) Uani 1 1 d .
H06A H 0.3287 0.2507 0.4893 0.026 Uiso 1 1 calc R
H06B H 0.4940 0.3359 0.5095 0.026 Uiso 1 1 calc R
C07 C 0.2569(4) 0.4374(4) 0.3185(3) 0.0179(6) Uani 1 1 d .
C08 C 0.5290(4) 0.2904(4) 0.1975(3) 0.0181(6) Uani 1 1 d .
C09 C 0.6436(5) 0.5603(4) 0.1521(3) 0.0203(7) Uani 1 1 d .
H09A H 0.5623 0.6290 0.1975 0.024 Uiso 1 1 calc R
H09B H 0.5966 0.5612 0.0847 0.024 Uiso 1 1 calc R
C10 C 0.8282(5) 0.6243(4) 0.1274(3) 0.0251(8) Uani 1 1 d .
H10A H 0.8222 0.7351 0.0896 0.038 Uiso 1 1 calc R
H10B H 0.9073 0.5558 0.0822 0.038 Uiso 1 1 calc R
H10C H 0.8733 0.6229 0.1947 0.038 Uiso 1 1 calc R
C11 C 0.7318(5) 0.2407(4) 0.0286(3) 0.0218(7) Uani 1 1 d .
H11A H 0.8200 0.2087 0.0771 0.026 Uiso 1 1 calc R
H11B H 0.7583 0.3480 -0.0130 0.026 Uiso 1 1 calc R
C12 C 0.7380(6) 0.1150(5) -0.0481(3) 0.0277(8) Uani 1 1 d .
H12A H 0.8560 0.1077 -0.0910 0.041 Uiso 1 1 calc R
H12B H 0.6503 0.1481 -0.0957 0.041 Uiso 1 1 calc R
H12C H 0.7117 0.0094 -0.0060 0.041 Uiso 1 1 calc R
C13 C 0.0556(5) 0.2430(5) 0.3137(3) 0.0227(7) Uani 1 1 d .
H13A H -0.0319 0.3048 0.2721 0.027 Uiso 1 1 calc R
H13B H 0.0014 0.1464 0.3573 0.027 Uiso 1 1 calc R
C14 C 0.0979(5) 0.6851(5) 0.3654(3) 0.0260(8) Uani 1 1 d .
H14A H 0.0608 0.7938 0.3331 0.039 Uiso 1 1 calc R
H14B H 0.1737 0.6930 0.4182 0.039 Uiso 1 1 calc R
H14C H -0.0065 0.6275 0.4009 0.039 Uiso 1 1 calc R
O01 O 0.5515(3) 0.2465(3) 0.09113(19) 0.0193(5) Uani 1 1 d .
O02 O 0.6588(3) 0.3930(3) 0.20936(19) 0.0178(5) Uani 1 1 d .
O03 O 0.6778(3) 0.1038(3) 0.44632(19) 0.0207(5) Uani 1 1 d .
O04 O 0.3829(3) 0.4511(3) 0.38696(19) 0.0199(5) Uani 1 1 d .
O05 O 0.1176(3) 0.3434(3) 0.38183(19) 0.0212(5) Uani 1 1 d .
O06 O 0.1960(3) 0.5971(3) 0.28151(19) 0.0203(5) Uani 1 1 d .
Cl Cl 0.71377(11) -0.01469(10) 0.24719(7) 0.0228(2) Uani 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
C02 C01 C07 103.5(3)
C02 C01 C08 103.8(3)
C07 C01 C08 118.8(3)
C13 C02 C01 102.2(3)
C13 C02 C03 113.6(3)
C01 C02 C03 105.2(3)
C02 C03 C04 107.6(3)
C05 C04 C03 111.6(3)
C05 C04 C08 112.2(3)
C03 C04 C08 104.0(3)
C05 C04 Cl 106.9(2)
C03 C04 Cl 109.7(2)
C08 C04 Cl 112.4(2)
O03 C05 C06 118.0(3)
O03 C05 C04 121.1(3)
C06 C05 C04 120.6(3)
O04 C06 C05 118.0(3)
O06 C07 O04 106.3(3)
O06 C07 O05 112.5(3)
O04 C07 O05 107.5(3)
O06 C07 C01 107.3(3)
O04 C07 C01 116.2(3)
O05 C07 C01 107.2(3)
O02 C08 O01 112.9(3)
O02 C08 C01 118.6(3)
O01 C08 C01 102.7(3)
O02 C08 C04 108.0(3)
O01 C08 C04 111.3(3)
C01 C08 C04 102.9(2)
O02 C09 C10 107.6(3)
O01 C11 C12 107.1(3)
O05 C13 C02 103.7(3)
C08 O01 C11 118.2(2)
C08 O02 C09 115.5(2)
C07 O04 C06 117.0(3)
C07 O05 C13 108.9(3)
C07 O06 C14 114.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C01 C02 1.540(5)
C01 C07 1.541(5)
C01 C08 1.545(4)
C02 C13 1.520(5)
C02 C03 1.542(5)
C03 C04 1.551(5)
C04 C05 1.543(5)
C04 C08 1.560(5)
C04 Cl 1.801(3)
C05 O03 1.210(4)
C05 C06 1.521(5)
C06 O04 1.420(4)
C07 O06 1.388(4)
C07 O04 1.409(4)
C07 O05 1.412(4)
C08 O02 1.391(4)
C08 O01 1.415(4)
C09 O02 1.453(4)
C09 C10 1.498(5)
C11 O01 1.449(4)
C11 C12 1.514(5)
C13 O05 1.437(4)
C14 O06 1.434(4)
