Catalyst-Free Cyclization of Anthranils and Cyclic Amines: One-step Synthesis of Rutaecarpine
Li, Jian; wang, zheng-bing; xu, yue; lu, xue-chen; zhu, shang-rong; Liu, Li; Chemical Communications  (2019) –; doi:10.1039/C9CC06160F

data_7124155
_publ_section_title
;
 Catalyst-Free Cyclization of Anthranils and Cyclic Amines: One-step
 Synthesis of Rutaecarpine
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06160F
_journal_year                    2019
_chemical_formula_sum            'C24 H20 Br Cl N2 O2'
_chemical_formula_weight         483.78
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-26 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.480(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4651(6)
_cell_length_b                   10.5710(5)
_cell_length_c                   17.7266(9)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      54.01
_cell_measurement_theta_min      3.48
_cell_volume                     2070.48(18)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16566
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.028
_diffrn_reflns_theta_min         3.605
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0600P)^2^+2.6738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3644
_reflns_number_total             3782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06160f2.cif
_cod_data_source_block           201900723ZH_LIULI_SBS_0m_a
_cod_database_code               7124155
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.755
_shelx_res_checksum              8824