Synthetic and crystallographic studies of bicyclo[3.3.1]nonane derivatives: from strong to weak hydrogen bonds and the stereochemistry of network formation
Wallentin, Carl-Johan; Orentas, Edvinas; Johnson, Magnus T.; Báthori, Nikoletta B.; Butkus, Eugenijus; Wendt, Ola F.; Wärnmark, Kenneth; Öhrström, Lars; CrystEngComm 14 (2012) 178–; doi:10.1039/c1ce05673e

data_7206957
_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
_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       \w-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/[\s^2^(Fo^2^)+(0.0665P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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