#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:11:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178939 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/68/4116880.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_4116880
loop_
_publ_author_name
'Leo A. Paquette'
'David G. Bolin'
'Marshall Stepanian'
'Bruce M. Branan'
'Uppuluri V. Mallavadhani'
'Jinsung Tae'
'Shawn W. E. Eisenberg'
'Robin D. Rogers'
_publ_section_title
;
 Intramolecular Oxymercuration of Stereoisomeric Cyclohexyl-Belted
 Poly(spirotetrahydrofuranyl) Platforms
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11603
_journal_page_last               11615
_journal_paper_doi               10.1021/ja981756p
_journal_volume                  120
_journal_year                    1998
_chemical_formula_structural     'LAP224 (I-SE-207B)'
_chemical_formula_sum            'C18 H25 Cl Hg O5'
_chemical_formula_weight         557.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.5772(7)
_cell_length_b                   9.4092(3)
_cell_length_c                   16.9302(5)
_cell_measurement_reflns_used    4799
_cell_measurement_temperature    173(2)
_cell_volume                     3596.54(19)
_computing_cell_refinement       'Siemens SAINT'
_computing_data_collection       'Siemens SAINT'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens SMART CCD'
_diffrn_measurement_method       'area detector'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12886
_diffrn_reflns_theta_max         27.84
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    8.734
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.00073(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.002
_refine_ls_goodness_of_fit_obs   1.068
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.402
_refine_ls_restrained_S_obs      1.068
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_obs          0.0261
_refine_ls_shift/esd_max         -0.005
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      '0.0239, 0.0000'
_refine_ls_wR_factor_all         0.0795
_refine_ls_wR_factor_obs         0.0491
_reflns_number_observed          2665
_reflns_number_total             3947
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja981756p_09.cif
_cod_data_source_block           54
_cod_original_cell_volume        3596.5(2)
_cod_database_code               4116880
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
Hg Hg 0.851388(7) -0.49373(2) 0.234653(10) 0.02228(7) Uani 1 d .
Cl Cl 0.90899(5) -0.65180(12) 0.30616(8) 0.0352(3) Uani 1 d .
O1 O 0.74421(14) -0.1815(3) 0.2329(2) 0.0439(10) Uani 1 d .
O2 O 0.82182(12) 0.0295(3) 0.2401(2) 0.0220(7) Uani 1 d .
O3 O 0.85354(12) -0.0096(3) 0.0927(2) 0.0229(6) Uani 1 d .
O4 O 0.93536(12) -0.3132(3) 0.1697(2) 0.0206(7) Uani 1 d .
O5 O 0.86377(14) -0.4595(3) 0.0630(2) 0.0301(8) Uani 1 d .
C1 C 0.8062(2) -0.3448(4) 0.1646(3) 0.0219(10) Uani 1 d .
H1A H 0.7676(2) -0.3872(4) 0.1476(3) 0.026 Uiso 1 calc R
C2 C 0.7938(2) -0.2090(4) 0.2084(3) 0.0247(11) Uani 1 d .
C3 C 0.8453(2) -0.1080(4) 0.2243(3) 0.0200(10) Uani 1 d .
C4 C 0.8865(2) -0.0896(4) 0.1509(2) 0.0163(9) Uani 1 d .
C5 C 0.9013(2) -0.2351(4) 0.1108(2) 0.0178(9) Uani 1 d .
C6 C 0.8444(2) -0.3200(4) 0.0914(3) 0.0224(10) Uani 1 d .
C7 C 0.8771(2) -0.1550(4) 0.3020(3) 0.0243(10) Uani 1 d .
H7A H 0.8584(2) -0.2412(4) 0.3244(3) 0.029 Uiso 1 calc R
H7B H 0.9196(2) -0.1747(4) 0.2922(3) 0.029 Uiso 1 calc R
C8 C 0.8695(2) -0.0268(5) 0.3580(3) 0.0315(12) Uani 1 d .
H8A H 0.8615(2) -0.0583(5) 0.4127(3) 0.038 Uiso 1 calc R
H8B H 0.9051(2) 0.0346(5) 0.3577(3) 0.038 Uiso 1 calc R
C9 C 0.8168(2) 0.0493(5) 0.3234(3) 0.0298(12) Uani 1 d .
H9A H 0.7793(2) 0.0079(5) 0.3434(3) 0.036 Uiso 1 calc R
H9B H 0.8177(2) 0.1517(5) 0.3370(3) 0.036 Uiso 1 calc R
C10 C 0.9413(2) 0.0009(4) 0.1708(3) 0.0236(9) Uani 1 d .
H10A H 0.9397(2) 0.0343(4) 0.2262(3) 0.028 Uiso 1 calc R
H10B H 0.9780(2) -0.0547(4) 0.1631(3) 0.028 Uiso 1 calc R
C11 C 0.9392(2) 0.1260(5) 0.1140(3) 0.0309(12) Uani 1 d .
H11A H 0.9534(2) 0.2141(5) 0.1397(3) 0.037 Uiso 1 calc R
H11B H 0.9634(2) 0.1074(5) 0.0664(3) 0.037 Uiso 1 calc R
C12 C 0.8744(2) 0.1367(4) 0.0933(3) 0.0297(11) Uani 1 d .
H12A H 0.8528(2) 0.1933(4) 0.1333(3) 0.036 Uiso 1 calc R
H12B H 0.8689(2) 0.1814(4) 0.0409(3) 0.036 Uiso 1 calc R
C13 C 0.9434(2) -0.2229(5) 0.0388(3) 0.0247(10) Uani 1 d .
H13A H 0.9265(2) -0.2729(5) -0.0074(3) 0.030 Uiso 1 calc R
H13B H 0.9497(2) -0.1219(5) 0.0247(3) 0.030 Uiso 1 calc R
C14 C 1.0019(2) -0.2916(5) 0.0636(3) 0.0322(12) Uani 1 d .
H14A H 1.0189(2) -0.3486(5) 0.0199(3) 0.039 Uiso 1 calc R
H14B H 1.0311(2) -0.2189(5) 0.0800(3) 0.039 Uiso 1 calc R
C15 C 0.9846(2) -0.3847(5) 0.1318(3) 0.0269(11) Uani 1 d .
H15A H 0.9726(2) -0.4801(5) 0.1130(3) 0.032 Uiso 1 calc R
H15B H 1.0181(2) -0.3956(5) 0.1691(3) 0.032 Uiso 1 calc R
C16 C 0.8074(2) -0.2595(5) 0.0230(3) 0.0309(12) Uani 1 d .
H16A H 0.7747(2) -0.1994(5) 0.0430(3) 0.037 Uiso 1 calc R
H16B H 0.8323(2) -0.2024(5) -0.0132(3) 0.037 Uiso 1 calc R
C17 C 0.7835(2) -0.3913(5) -0.0184(3) 0.0399(14) Uani 1 d .
H17A H 0.7468(2) -0.4259(5) 0.0071(3) 0.048 Uiso 1 calc R
H17B H 0.7755(2) -0.3724(5) -0.0750(3) 0.048 Uiso 1 calc R
C18 C 0.8335(3) -0.4954(6) -0.0082(3) 0.0418(13) Uani 1 d .
H18A H 0.8178(3) -0.5935(6) -0.0050(3) 0.050 Uiso 1 calc R
H18B H 0.8609(3) -0.4897(6) -0.0538(3) 0.050 Uiso 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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
C1 Hg Cl 174.83(12)
C3 O2 C9 109.5(3)
C4 O3 C12 108.8(3)
C15 O4 C5 109.7(3)
C18 O5 C6 110.2(3)
C2 C1 C6 112.1(3)
C2 C1 Hg 112.2(3)
C6 C1 Hg 106.6(3)
O1 C2 C1 121.3(4)
O1 C2 C3 120.5(4)
C1 C2 C3 118.2(4)
O2 C3 C2 108.3(3)
O2 C3 C7 105.7(3)
C2 C3 C7 108.8(3)
O2 C3 C4 105.7(3)
C2 C3 C4 112.5(4)
C7 C3 C4 115.3(3)
O3 C4 C10 105.9(3)
O3 C4 C3 107.1(3)
C10 C4 C3 111.5(3)
O3 C4 C5 105.6(3)
C10 C4 C5 114.0(3)
C3 C4 C5 112.1(3)
O4 C5 C13 104.5(3)
O4 C5 C6 108.8(3)
C13 C5 C6 112.4(4)
O4 C5 C4 104.8(3)
C13 C5 C4 114.1(3)
C6 C5 C4 111.5(3)
O5 C6 C1 107.3(3)
O5 C6 C16 104.3(4)
C1 C6 C16 111.2(4)
O5 C6 C5 106.5(3)
C1 C6 C5 112.0(4)
C16 C6 C5 114.8(3)
C8 C7 C3 104.2(3)
C9 C8 C7 102.8(4)
O2 C9 C8 105.0(3)
C11 C10 C4 105.4(3)
C12 C11 C10 103.2(3)
O3 C12 C11 104.6(3)
C14 C13 C5 106.5(4)
C15 C14 C13 103.5(4)
O4 C15 C14 105.6(3)
C17 C16 C6 103.7(4)
C18 C17 C16 102.2(4)
O5 C18 C17 107.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Hg C1 2.100(4)
Hg Cl 2.3172(11)
O1 C2 1.221(5)
O2 C3 1.425(4)
O2 C9 1.427(6)
O3 C4 1.446(4)
O3 C12 1.455(4)
O4 C15 1.449(5)
O4 C5 1.459(4)
O5 C18 1.428(6)
O5 C6 1.465(5)
C1 C2 1.504(6)
C1 C6 1.527(6)
C2 C3 1.527(6)
C3 C7 1.562(6)
C3 C4 1.560(6)
C4 C10 1.539(5)
C4 C5 1.564(5)
C5 C13 1.549(6)
C5 C6 1.548(5)
C6 C16 1.537(6)
C7 C8 1.544(6)
C8 C9 1.508(7)
C10 C11 1.521(6)
C11 C12 1.508(6)
C13 C14 1.530(6)
C14 C15 1.502(6)
C16 C17 1.523(6)
C17 C18 1.505(7)
