#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:36:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180400 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/69/7206957.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_7206957
loop_
_publ_author_name
'Wallentin, Carl-Johan'
'Orentas, Edvinas'
'Johnson, Magnus T.'
'Báthori, Nikoletta B.'
'Butkus, Eugenijus'
'Wendt, Ola F.'
'Wärnmark, Kenneth'
'Öhrström, Lars'
_publ_section_title
;
 Synthetic and crystallographic studies of bicyclo[3.3.1]nonane
 derivatives: from strong to weak hydrogen bonds and the stereochemistry
 of network formation
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              178
_journal_paper_doi               10.1039/c1ce05673e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C9 H8 O2'
_chemical_formula_sum            'C9 H8 O2'
_chemical_formula_weight         148.16
_chemical_name_systematic
;
?
;
_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                 100.854(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8088(3)
_cell_length_b                   7.4891(4)
_cell_length_c                   14.8396(8)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.0171
_cell_measurement_theta_min      2.7088
_cell_volume                     743.16(7)
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7381
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         33.09
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86049
_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    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0412
_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)+(0.0665P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                1366
_reflns_number_total             2627
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05673e.txt
_cod_data_source_block           compound2
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7206957
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 0.59248(12) 0.26746(12) 0.04561(6) 0.0725(3) Uani 1 1 d .
O2 O 0.02841(15) 0.16930(16) 0.29355(6) 0.0910(3) Uani 1 1 d .
C3 C 0.49715(15) 0.09000(14) 0.22993(7) 0.0516(3) Uani 1 1 d .
H3 H 0.6323 0.0891 0.2563 0.062 Uiso 1 1 calc R
C4 C 0.43737(14) 0.05408(14) 0.12905(7) 0.0489(3) Uani 1 1 d .
H4 H 0.5301 -0.0324 0.1104 0.059 Uiso 1 1 calc R
C5 C 0.44456(15) 0.22636(14) 0.07626(7) 0.0502(3) Uani 1 1 d .
C6 C 0.10486(16) 0.29107(17) 0.09762(8) 0.0600(3) Uani 1 1 d .
H6 H -0.0026 0.3696 0.0917 0.072 Uiso 1 1 calc R
C7 C 0.15056(17) 0.13619(16) 0.24554(8) 0.0590(3) Uani 1 1 d .
C8 C 0.08867(15) 0.11330(18) 0.14235(8) 0.0577(3) Uani 1 1 d .
H8 H -0.0500 0.0713 0.1276 0.069 Uiso 1 1 calc R
C9 C 0.26675(17) 0.34041(16) 0.06626(7) 0.0575(3) Uani 1 1 d .
H9 H 0.2674 0.4503 0.0371 0.069 Uiso 1 1 calc R
C10 C 0.36556(17) 0.12289(15) 0.28281(7) 0.0558(3) Uani 1 1 d .
H10 H 0.4105 0.1381 0.3455 0.067 Uiso 1 1 calc R
C11 C 0.22486(16) -0.02207(16) 0.10848(8) 0.0559(3) Uani 1 1 d .
H11A H 0.1826 -0.0415 0.0431 0.067 Uiso 1 1 calc R
H11B H 0.2200 -0.1352 0.1398 0.067 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0603(5) 0.0832(6) 0.0828(6) 0.0088(4) 0.0362(5) -0.0019(4)
O2 0.0816(7) 0.1227(9) 0.0810(6) -0.0003(6) 0.0465(5) 0.0191(6)
C3 0.0445(5) 0.0511(6) 0.0566(7) 0.0053(5) 0.0027(5) 0.0021(4)
C4 0.0417(5) 0.0511(6) 0.0559(6) -0.0039(4) 0.0144(4) 0.0050(4)
C5 0.0452(6) 0.0614(7) 0.0458(6) -0.0028(5) 0.0129(4) -0.0025(5)
C6 0.0437(6) 0.0768(8) 0.0569(7) 0.0046(6) 0.0025(5) 0.0153(5)
C7 0.0580(7) 0.0638(7) 0.0606(7) 0.0030(5) 0.0249(5) 0.0044(5)
C8 0.0342(5) 0.0780(8) 0.0618(7) -0.0018(5) 0.0114(5) -0.0043(5)
C9 0.0584(7) 0.0622(7) 0.0510(6) 0.0094(5) 0.0080(5) 0.0087(5)
C10 0.0640(7) 0.0571(6) 0.0453(6) 0.0027(5) 0.0076(5) 0.0015(5)
C11 0.0516(6) 0.0592(7) 0.0578(6) -0.0097(5) 0.0125(5) -0.0093(5)
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 C3 C4 122.66(9)
C10 C3 H3 118.7
C4 C3 H3 118.7
C3 C4 C5 109.53(8)
C3 C4 C11 109.53(8)
C5 C4 C11 109.59(8)
C3 C4 H4 109.4
C5 C4 H4 109.4
C11 C4 H4 109.4
O1 C5 C9 122.63(11)
O1 C5 C4 121.13(10)
C9 C5 C4 116.23(9)
C9 C6 C8 122.49(10)
C9 C6 H6 118.8
C8 C6 H6 118.8
O2 C7 C10 122.40(11)
O2 C7 C8 121.47(10)
C10 C7 C8 116.10(9)
C6 C8 C11 110.17(9)
C6 C8 C7 108.43(10)
C11 C8 C7 109.72(9)
C6 C8 H8 109.5
C11 C8 H8 109.5
C7 C8 H8 109.5
C6 C9 C5 121.79(11)
C6 C9 H9 119.1
C5 C9 H9 119.1
C3 C10 C7 121.93(10)
C3 C10 H10 119.0
C7 C10 H10 119.0
C8 C11 C4 107.32(9)
C8 C11 H11A 110.3
C4 C11 H11A 110.3
C8 C11 H11B 110.3
C4 C11 H11B 110.3
H11A C11 H11B 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2200(12)
O2 C7 1.2181(12)
C3 C10 1.3207(14)
C3 C4 1.4998(14)
C3 H3 0.9300
C4 C5 1.5150(15)
C4 C11 1.5316(14)
C4 H4 0.9800
C5 C9 1.4662(15)
C6 C9 1.3272(16)
C6 C8 1.5009(17)
C6 H6 0.9300
C7 C10 1.4676(17)
C7 C8 1.5194(15)
C8 C11 1.5218(16)
C8 H8 0.9800
C9 H9 0.9300
C10 H10 0.9300
C11 H11A 0.9700
C11 H11B 0.9700
