N-Acyl-Glutarimides: Effect of Glutarimide Ring on the Structures of Fully Perpendicular Twisted Amides and N-C Bond Cross-Coupling.
Rahman, Md Mahbubur; Liu, Chengwei; Bisz, Elwira; Dziuk, Błażej; Lalancette, Roger A.; Wang, Qi; Chen, Hao; Szostak, Roman; Szostak, Michal; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00227

data_4038196
_publ_section_title
;
 N-Acyl-Glutarimides: Effect of Glutarimide Ring on the Structures of
 Fully Perpendicular Twisted Amides and N-C Bond Cross-Coupling.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00227
_journal_year                    2020
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.249(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.674(2)
_cell_length_b                   8.4545(5)
_cell_length_c                   10.8501(7)
_cell_measurement_reflns_used    8836
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.000
_cell_measurement_theta_min      3.084
_cell_volume                     2693.9(3)
_computing_cell_refinement       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_data_reduction        'CrysAlisCCD (Oxford Diffraction Ltd., 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       \w--scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8836
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94260
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1552
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1238P)^2^+0.4798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2038
_refine_ls_wR_factor_ref         0.2456
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1215
_reflns_number_total             2642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00227_si_002.cif
_cod_data_source_block           BD363_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038196
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.57 (release 26-01-2010 CrysAlis171 .NET)
(compiled Jan 26 2010,14:36:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_shelx_res_checksum              73790
_shelx_hkl_checksum              96954