Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework.
Zonker, Benjamin; Becker, Jonathan; Hrdina, Radim; Organic & biomolecular chemistry 19 (2021) 4027–4031; doi:10.1039/d1ob00471a

data_7158016
_publ_section_title
;
 Synthesis of noradamantane derivatives by ring-contraction of the
 adamantane framework.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4027
_journal_page_last               4031
_journal_paper_doi               10.1039/d1ob00471a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28
_chemical_name_common            14
_chemical_name_systematic        'Nordiamantane carboxylic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-15 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.934(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5170(4)
_cell_length_b                   10.4112(7)
_cell_length_c                   15.8832(10)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.06
_cell_measurement_theta_min      2.35
_cell_volume                     1067.36(12)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            77056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.019
_diffrn_reflns_theta_min         2.346
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.6060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00471a2.cif
_cod_data_source_block           D19288
_cod_depositor_comments          'Adding full bibliography for 7158016.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158016
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              73635