FeCl3 promoted ring size dictating diversity-oriented synthesis (DOS) of N-heterocycles using in situ generated cyclic imines and enamines
Dhandabani, Ganesh Kumar; Mutra, Mohana Reddy; Wang, Jeh-Jeng; Chemical Communications  (2019) –; doi:10.1039/C9CC03375K

data_7123595
_publ_section_title
;
 FeCl3 promoted ring size dictating diversity-oriented synthesis (DOS) of
 N-heterocycles using in situ generated cyclic imines and enamines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03375K
_journal_year                    2019
_chemical_formula_moiety         'C24 H19 N, 0.45(H2 O)'
_chemical_formula_sum            'C24 H19.9 N O0.45'
_chemical_formula_weight         329.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-24 deposited with the CCDC.    2019-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                104.8513(17)
_cell_angle_beta                 109.5128(15)
_cell_angle_gamma                108.1988(15)
_cell_formula_units_Z            2
_cell_length_a                   9.2367(4)
_cell_length_b                   10.2565(5)
_cell_length_c                   11.0747(6)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.337
_cell_measurement_theta_min      3.203
_cell_volume                     859.89(8)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28959
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         3.203
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             349
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.3169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2774
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03375k2.cif
_cod_data_source_block           th4036
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        859.89(7)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C24 H19.90 N O0.45'
_cod_database_code               7123595
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              97275