#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/11/7201113.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_7201113
loop_
_publ_author_name
'Wallentin, Carl-Johan'
'Orentas, Edvinas'
'Johnson, Magnus T.'
'Butkus, Eugenijus'
'Wendt, Ola F.'
'Öhrström, Lars'
'Wärnmark, Kenneth'
_publ_section_title
;
 Network analysis of bicyclo[3.3.1]nonanes: the diol, the dione and the
 acetal
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1837
_journal_paper_doi               10.1039/b905122h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.287(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4565(6)
_cell_length_b                   7.9243(4)
_cell_length_c                   13.7482(8)
_cell_measurement_reflns_used    2405
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.1056
_cell_measurement_theta_min      2.5660
_cell_volume                     1198.04(12)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1829
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Xcalibur 3'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7626
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET)
(compiled Aug 28 2006,13:05:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0428
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                1261
_reflns_number_total             2187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905122h.txt
_cod_data_source_block           compound4
_cod_original_cell_volume        1198.04(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7201113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44474(13) 0.24402(17) 0.02657(10) 0.0529(4) Uani 1 1 d . . .
O2 O 0.42474(14) -0.20880(19) 0.33638(12) 0.0677(5) Uani 1 1 d . . .
O3 O 0.44270(14) 0.42468(17) 0.15201(11) 0.0568(4) Uani 1 1 d . . .
O4 O 0.62345(13) -0.13569(19) 0.39271(11) 0.0609(5) Uani 1 1 d . . .
C5 C 0.46153(18) 0.2520(2) 0.13370(14) 0.0429(5) Uani 1 1 d . . .
C6 C 0.51104(18) -0.0879(2) 0.32251(15) 0.0450(5) Uani 1 1 d . . .
C7 C 0.51824(18) -0.0957(2) 0.21333(15) 0.0452(5) Uani 1 1 d . . .
H7 H 0.5350 -0.2127 0.1985 0.054 Uiso 1 1 calc R . .
C8 C 0.59228(19) 0.2063(2) 0.18768(16) 0.0516(6) Uani 1 1 d . . .
H8A H 0.6122 0.2498 0.2563 0.062 Uiso 1 1 calc R . .
H8B H 0.6453 0.2614 0.1535 0.062 Uiso 1 1 calc R . .
C9 C 0.36880(17) 0.1378(2) 0.16198(14) 0.0448(5) Uani 1 1 d . . .
H9 H 0.2881 0.1662 0.1176 0.054 Uiso 1 1 calc R . .
C10 C 0.39530(19) -0.0459(2) 0.14220(15) 0.0495(6) Uani 1 1 d . . .
H10A H 0.3321 -0.1183 0.1537 0.059 Uiso 1 1 calc R . .
H10B H 0.3965 -0.0594 0.0724 0.059 Uiso 1 1 calc R . .
C11 C 0.4730(2) 0.0826(3) 0.35195(16) 0.0573(6) Uani 1 1 d . . .
H11A H 0.5410 0.1600 0.3626 0.069 Uiso 1 1 calc R . .
H11B H 0.4524 0.0721 0.4155 0.069 Uiso 1 1 calc R . .
C12 C 0.61787(19) 0.0174(3) 0.19196(16) 0.0520(6) Uani 1 1 d . . .
H12A H 0.6933 -0.0031 0.2442 0.062 Uiso 1 1 calc R . .
H12B H 0.6302 -0.0168 0.1278 0.062 Uiso 1 1 calc R . .
C13 C 0.3646(2) 0.1555(3) 0.27219(15) 0.0574(6) Uani 1 1 d . . .
H13A H 0.3581 0.2744 0.2866 0.069 Uiso 1 1 calc R . .
H13B H 0.2914 0.1006 0.2786 0.069 Uiso 1 1 calc R . .
C14 C 0.3555(2) 0.3660(3) -0.01899(16) 0.0609(6) Uani 1 1 d . . .
H14A H 0.2770 0.3128 -0.0470 0.073 Uiso 1 1 calc R . .
H14B H 0.3780 0.4251 -0.0728 0.073 Uiso 1 1 calc R . .
C15 C 0.3513(2) 0.4856(3) 0.06502(17) 0.0633(7) Uani 1 1 d . . .
H15A H 0.3694 0.6000 0.0486 0.076 Uiso 1 1 calc R . .
H15B H 0.2718 0.4840 0.0770 0.076 Uiso 1 1 calc R . .
C16 C 0.6169(2) -0.3091(3) 0.4122(2) 0.0744(8) Uani 1 1 d . . .
H16A H 0.6551 -0.3333 0.4832 0.089 Uiso 1 1 calc R . .
H16B H 0.6572 -0.3745 0.3714 0.089 Uiso 1 1 calc R . .
C17 C 0.4863(2) -0.3492(3) 0.38503(19) 0.0738(8) Uani 1 1 d . . .
H17A H 0.4689 -0.4466 0.3405 0.089 Uiso 1 1 calc R . .
H17B H 0.4616 -0.3744 0.4454 0.089 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C5 107.22(14) . . ?
C17 O2 C6 109.02(17) . . ?
C5 O3 C15 106.77(15) . . ?
C16 O4 C6 107.58(16) . . ?
O3 C5 O1 104.01(14) . . ?
O3 C5 C8 108.79(15) . . ?
O1 C5 C8 108.78(16) . . ?
O3 C5 C9 112.03(16) . . ?
O1 C5 C9 109.47(16) . . ?
C8 C5 C9 113.32(16) . . ?
O2 C6 O4 105.00(15) . . ?
O2 C6 C11 107.57(17) . . ?
O4 C6 C11 109.28(17) . . ?
O2 C6 C7 109.52(17) . . ?
O4 C6 C7 111.51(16) . . ?
C11 C6 C7 113.54(16) . . ?
C10 C7 C6 108.97(16) . . ?
C10 C7 C12 109.10(16) . . ?
C6 C7 C12 114.21(17) . . ?
C10 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C12 C7 H7 108.1 . . ?
C5 C8 C12 113.99(17) . . ?
C5 C8 H8A 108.8 . . ?
C12 C8 H8A 108.8 . . ?
C5 C8 H8B 108.8 . . ?
C12 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C5 C9 C10 109.42(16) . . ?
C5 C9 C13 114.45(17) . . ?
C10 C9 C13 108.99(16) . . ?
C5 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C13 C9 H9 107.9 . . ?
C7 C10 C9 109.06(15) . . ?
C7 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C7 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C6 C11 C13 112.68(18) . . ?
C6 C11 H11A 109.1 . . ?
C13 C11 H11A 109.1 . . ?
C6 C11 H11B 109.1 . . ?
C13 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C8 C12 C7 115.70(17) . . ?
C8 C12 H12A 108.4 . . ?
C7 C12 H12A 108.4 . . ?
C8 C12 H12B 108.4 . . ?
C7 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C11 C13 C9 115.55(17) . . ?
C11 C13 H13A 108.4 . . ?
C9 C13 H13A 108.4 . . ?
C11 C13 H13B 108.4 . . ?
C9 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
O1 C14 C15 105.34(17) . . ?
O1 C14 H14A 110.7 . . ?
C15 C14 H14A 110.7 . . ?
O1 C14 H14B 110.7 . . ?
C15 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
O3 C15 C14 104.75(17) . . ?
O3 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
O3 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
O4 C16 C17 105.55(19) . . ?
O4 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
O4 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
O2 C17 C16 107.01(19) . . ?
O2 C17 H17A 110.3 . . ?
C16 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
C16 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.418(2) . ?
O1 C5 1.432(2) . ?
O2 C17 1.385(3) . ?
O2 C6 1.428(2) . ?
O3 C5 1.418(2) . ?
O3 C15 1.434(2) . ?
O4 C16 1.406(3) . ?
O4 C6 1.427(2) . ?
C5 C8 1.517(3) . ?
C5 C9 1.527(3) . ?
C6 C11 1.509(3) . ?
C6 C7 1.527(3) . ?
C7 C10 1.524(3) . ?
C7 C12 1.543(3) . ?
C7 H7 0.9800 . ?
C8 C12 1.523(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(3) . ?
C9 C13 1.536(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.522(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.471(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 493121
