Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates.
Yang, Yuwen; Yang, Weibo; Chemical communications (Cambridge, England) 54 (2018) 12182–12185; doi:10.1039/c8cc06945j

data_7122414
_publ_section_title
;
 Divergent synthesis of N-heterocycles by Pd-catalyzed controllable
 cyclization of vinylethylene carbonates.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12182
_journal_page_last               12185
_journal_paper_doi               10.1039/c8cc06945j
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.31
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-02 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.110(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.587(6)
_cell_length_b                   6.230(3)
_cell_length_c                   15.598(7)
_cell_measurement_reflns_used    419
_cell_measurement_temperature    173
_cell_measurement_theta_max      17.805
_cell_measurement_theta_min      2.61
_cell_volume                     1319.4(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9583
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.343
_diffrn_reflns_theta_min         1.952
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0844 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.8672. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     202
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0350P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1277
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06945j2.cif
_cod_data_source_block           mo_2017968_0m
_cod_depositor_comments
'Adding full bibliography for 7122414--7122415.cif.'
_cod_database_code               7122414
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O0AA-C11 \\sim O1-C11 \\sim O1-C10 \\sim O0AA-C10
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: O1(0.85) H11A(0.85) H11B(0.85) H11C(0.15) H11D(0.15) H10A(0.85)
 H10B(0.85) H10C(0.15) H10D(0.15) O0AA(0.15)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C11(H11C,H11D), C10(H10A,H10B), C10(H10C,H10D)
6.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C13(H13), C5(H5), C17(H17), C16(H16), C2(H2), C3(H3),
 C15(H15), C4(H4), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'