Synthesis of 6-methyl-3,4-dihydropyrazinones using an Ugi 4-CR/allenamide cycloisomerization protocol.
Icelo-Ávila, Estefanía; Amador-Sánchez, Yoarhy A; Polindara-García, Luis A; Miranda, Luis D.; Organic & biomolecular chemistry 15 (2017) 360–372; doi:10.1039/c6ob02266a

data_7155427
_publ_section_title
;
 Synthesis of 6-methyl-3,4-dihydropyrazinones using an Ugi 4-CR/allenamide
 cycloisomerization protocol.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              360
_journal_page_last               372
_journal_paper_doi               10.1039/c6ob02266a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39
_chemical_melting_point          150.5(15)
_chemical_name_systematic
N-(2,6-dimethylphenyl)-2-(N-(prop-2-yn-1-yl)acetamido)pentanamide
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.344(3)
_cell_length_b                   22.993(7)
_cell_length_c                   16.649(5)
_cell_measurement_reflns_used    3648
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.54
_cell_measurement_theta_min      2.45
_cell_volume                     3577.0(19)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'XP V 5.1 (Bruker, 1998)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/1 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1461
_diffrn_reflns_av_unetI/netI     0.1164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22418
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         2.153
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone-Hexanes'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0077(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1588
_refine_ls_R_factor_gt           0.0763
_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^)+(0.0957P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.2355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1886
_reflns_number_total             4111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02266a2.cif
_cod_data_source_block           376MGL14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '149-152' was changed to '150.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        3576.9(19)
_cod_database_code               7155427
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014-3
_shelx_res_checksum              1107