Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines.
Novikov, Mikhail S.; Rostovskii, Nikolai V.; Koronatov, Alexander N.; Zavyalov, Kirill V.; Zubakin, Grigory V.; Khlebnikov, Alexander F.; Starova, Galina L.; The Journal of organic chemistry 82 (2017) 13396–13404; doi:10.1021/acs.joc.7b02484

data_4033204
_publ_section_title
;
 Synthesis of 1,2-Dihydropyrimidine-2-carboxylates via Regioselective
 Addition of Rhodium(II) Carbenoids to 2H-Azirine-2-carbaldimines.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13396
_journal_page_last               13404
_journal_paper_doi               10.1021/acs.joc.7b02484
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C25 H21 Cl F6 N2 O4'
_chemical_formula_sum            'C25 H21 Cl F6 N2 O4'
_chemical_formula_weight         562.89
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-04
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                79.542(7)
_cell_angle_beta                 81.945(6)
_cell_angle_gamma                88.919(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5654(4)
_cell_length_b                   11.1449(9)
_cell_length_c                   14.5379(11)
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3400
_cell_measurement_theta_min      3.1350
_cell_volume                     1193.49(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
  1 omega    6.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000  -90.0000 45

  2 omega  -82.00    7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000   90.0000 89

  3 omega  -25.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   90.0000 49

  4 omega  -17.00   21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 38

  5 omega  -48.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000    0.0000 82

  6 omega  -54.00  -27.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -19.0000  -30.0000 27

  7 omega   17.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -19.0000  -30.0000 43

  8 omega   37.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000  -30.0000 55
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0382521000
_diffrn_orient_matrix_UB_12      0.0075128000
_diffrn_orient_matrix_UB_13      -0.0481224000
_diffrn_orient_matrix_UB_21      -0.0126545000
_diffrn_orient_matrix_UB_22      0.0639458000
_diffrn_orient_matrix_UB_23      -0.0048515000
_diffrn_orient_matrix_UB_31      0.0856927000
_diffrn_orient_matrix_UB_32      0.0065718000
_diffrn_orient_matrix_UB_33      0.0130675000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10307
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+0.3970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                3920
_reflns_number_total             5130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02484_si_002.cif
_cod_data_source_block           nms8_exo_exo_5b
_cod_depositor_comments
'Adding full bibliography for 4033202--4033205.cif.'
_cod_database_code               4033204
_chemical_oxdiff_formula         'C25 H21 Cl F6 N2 O4'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32