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_7206959
_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 H6 Br2 O2'
_chemical_formula_sum            'C9 H6 Br2 O2'
_chemical_formula_weight         305.96
_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                 107.353(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3618(7)
_cell_length_b                   6.6849(5)
_cell_length_c                   14.6052(11)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.0452
_cell_measurement_theta_min      2.1344
_cell_volume                     965.62(13)
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5869
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    8.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46789
_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    2.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.0710
_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^)+(0.1616P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2302
_refine_ls_wR_factor_ref         0.2735
_reflns_number_gt                592
_reflns_number_total             1678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05673e.txt
_cod_data_source_block           compound3
_cod_original_cell_volume        965.62(12)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7206959