Synthesis of diverse nitrogen-enriched heterocyclic scaffolds using a suite of tunable one-pot multicomponent reactions.
Martinez-Ariza, Guillermo; Ayaz, Muhammad; Medda, Federico; Hulme, Christopher; The Journal of organic chemistry 79 (2014) 5153–5162; doi:10.1021/jo500723d

data_4029456
_publ_section_title
;
 Synthesis of diverse nitrogen-enriched heterocyclic scaffolds using a
 suite of tunable one-pot multicomponent reactions.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5153
_journal_page_last               5162
_journal_paper_doi               10.1021/jo500723d
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H21 Cl N4 O'
_chemical_formula_sum            'C19 H21 Cl N4 O'
_chemical_formula_weight         356.85
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.49(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.583(3)
_cell_length_b                   8.075(3)
_cell_length_c                   28.833(14)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.62
_cell_volume                     1757.4(13)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      '100 '
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18849
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.42
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1350 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.7550.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.3138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                2780
_reflns_number_total             3669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500723d_si_002.cif
_cod_data_source_block           complete
_cod_depositor_comments
'Adding full bibliography for 4029456--4029458.cif.'
_cod_original_cell_volume        1757.3(13)
_cod_database_code               4029456
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, H10 of C10, H8 of C8, H16 of C16, {H18A,H18B} of C18, {H19A,H19B}
  of C19, H20 of C20, {H21A,H21B} of C21, H22 of C22, {H23A,H23B} of C23, H11
  of C11, H12 of C12, H13 of C13
 At 1.5 times of:
  {H24A,H24B,H24C} of C24
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C13(H13), C16(H16), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;