Hydrogen-bond-assisted organocatalytic acetalization of secondary alcohols: experimental and theoretical studies.
Rumyantsev, Misha; Sitnikov, Nikolay S.; Somov, Nikolay V.; The journal of physical chemistry. A 119 (2015) 4108–4117; doi:10.1021/acs.jpca.5b02102

data_1520293
_publ_section_title
;
 Hydrogen-bond-assisted organocatalytic acetalization of secondary
 alcohols: experimental and theoretical studies.
;
_journal_issue                   18
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              4108
_journal_page_last               4117
_journal_paper_doi               10.1021/acs.jpca.5b02102
_journal_volume                  119
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C5 H5 Br2 N'
_chemical_formula_weight         238.90
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-10T12:48:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2564(5)
_cell_length_b                   4.6063(2)
_cell_length_c                   10.7577(3)
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.298
_cell_measurement_theta_min      3.761
_cell_volume                     706.45(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0302
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0007135
_diffrn_orient_matrix_UB_12      -0.150665
_diffrn_orient_matrix_UB_13      0.0135979
_diffrn_orient_matrix_UB_21      0.0484348
_diffrn_orient_matrix_UB_22      -0.00934
_diffrn_orient_matrix_UB_23      -0.0144767
_diffrn_orient_matrix_UB_31      0.0113096
_diffrn_orient_matrix_UB_32      0.0305053
_diffrn_orient_matrix_UB_33      0.0628767
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10721
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    11.37
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0099(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                1598
_reflns_number_total             1749
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp5b02102_si_002.cif
_cod_data_source_block           hydcla_br_090913
_cod_database_code               1520293