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_7122415
_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         'C23 H20 Cl2 N2'
_chemical_formula_sum            'C23 H20 Cl2 N2'
_chemical_formula_weight         395.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-11
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8417(2)
_cell_length_b                   26.8280(9)
_cell_length_c                   28.4867(11)
_cell_measurement_reflns_used    5889
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.499
_cell_measurement_theta_min      3.103
_cell_volume                     4464.5(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      173.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        63.995
_diffrn_reflns_theta_max         63.995
_diffrn_reflns_theta_min         3.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1346 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.7156. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0470P)^2^+8.0463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2833
_reflns_number_total             3698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06945j2.cif
_cod_data_source_block           2017770-yyw-85_0m_sqd
_cod_depositor_comments
'Adding full bibliography for 7122414--7122415.cif.'
_cod_database_code               7122415
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.740
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C5(H5), C12(H12), C14(H14), C6(H6), C3(H3), C2(H2),
 C19(H19), C23(H23), C20(H20), C22(H22), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_olex2_submission_special_instructions 'No special instructions were received'