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_4029457
_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         'C18 H18 F N5 O3'
_chemical_formula_sum            'C18 H18 F N5 O3'
_chemical_formula_weight         371.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.482(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.4045(17)
_cell_length_b                   9.0833(8)
_cell_length_c                   17.5993(13)
_cell_measurement_reflns_used    6441
_cell_measurement_temperature    100.
_cell_measurement_theta_max      29.32
_cell_measurement_theta_min      2.32
_cell_volume                     3411.3(5)
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32986
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0574 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.9150.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0421P)^2^+3.5978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                3372
_reflns_number_total             4242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500723d_si_003.cif
_cod_data_source_block           mo_ch227_0m
_cod_depositor_comments
'Adding full bibliography for 4029456--4029458.cif.'
_cod_database_code               4029457
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C16(H16A,H16B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C2(H2), C12(H12), C10(H10), C6(H6), C3(H3), C5(H5)
;