Annulated carbamates are precursors for the ring contraction of the adamantane framework
Hrdina, Radim; Holovko-Kamoshenkova, Oksana M.; Císařová, Ivana; Koucký, Filip; Machalický, Oldřich; RSC Advances 12 (2022) 31056–31060; doi:10.1039/D2RA06402B

data_7245746
_publ_section_title
;
 Annulated carbamates are precursors for the ring contraction of the
 adamantane framework
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              31056
_journal_page_last               31060
_journal_paper_doi               10.1039/D2RA06402B
_journal_volume                  12
_journal_year                    2022
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C11 H20 N, Cl, H2 O'
_chemical_formula_sum            'C11 H22 Cl N O'
_chemical_formula_weight         219.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-04 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.171(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6281(13)
_cell_length_b                   6.4734(4)
_cell_length_c                   11.5542(9)
_cell_measurement_reflns_used    5351
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.1421
_cell_measurement_theta_min      2.5160
_cell_volume                     1210.98(15)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10958
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.516
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.442
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.6892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2180
_reflns_number_total             2773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra06402b2.cif
_cod_data_source_block           mo_rhe_73b_200k_org_hrdina
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245746
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              36968