Multicomponent Synthesis of 1,3-Diketone-Linked N-Substituted Pyrroles, Pyrrolo[1,2- a]pyrazines, Pyrrolo[1,4]diazepines, and Pyrrolo[1,4]diazocines.
Chithanna, Sivanna; Yang, Ding-Yah; The Journal of organic chemistry 84 (2019) 1339–1347; doi:10.1021/acs.joc.8b02819

data_4037556
_publ_section_title
;
 Multicomponent Synthesis of 1,3-Diketone-Linked N-Substituted Pyrroles,
 Pyrrolo[1,2- a]pyrazines, Pyrrolo[1,4]diazepines, and
 Pyrrolo[1,4]diazocines.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1339
_journal_page_last               1347
_journal_paper_doi               10.1021/acs.joc.8b02819
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                102.597(3)
_cell_angle_beta                 109.073(3)
_cell_angle_gamma                105.449(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2655(7)
_cell_length_b                   9.2448(8)
_cell_length_c                   10.7843(9)
_cell_measurement_reflns_used    9268
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.392
_cell_measurement_theta_min      2.960
_cell_volume                     707.31(11)
_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_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 0.995
_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  0.0373
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14035
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         3.442
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0565P)^2^+0.2829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2616
_reflns_number_total             2902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02819_si_002.cif
_cod_data_source_block           cs171
_cod_original_cell_volume        707.32(11)
_cod_database_code               4037556
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              15087
_shelx_hkl_checksum              51695