N-Heterocyclic Olefin Catalysis for the Ring Opening of Cyclic Amidine Compounds: A Pathway to the Synthesis of ε-Caprolactam- and γ-Lactam-Derived Amines.
Peixoto, Daniela; Malta, Gabriela; Cruz, Hugo; Barroso, Sónia; Carvalho, Ana Luísa; Ferreira, Luísa M; Branco, Paula S.; The Journal of organic chemistry 84 (2019) 3793–3800; doi:10.1021/acs.joc.8b02823

data_4034272
_publ_section_title
;
 N-Heterocyclic Olefin Catalysis for the Ring Opening of Cyclic Amidine
 Compounds: A Pathway to the Synthesis of \e-Caprolactam- and
 \g-Lactam-Derived Amines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3793
_journal_page_last               3800
_journal_paper_doi               10.1021/acs.joc.8b02823
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H17 N3 O3, H2 O'
_chemical_formula_sum            'C14 H19 N3 O4'
_chemical_formula_weight         293.32
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 122.388(6)
_cell_angle_gamma                90
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_cell_length_b                   4.9304(9)
_cell_length_c                   23.090(4)
_cell_measurement_reflns_used    3290
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.11
_cell_measurement_theta_min      3.20
_cell_volume                     2996.5(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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'Ortep3 for Windows v2.02 (L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565)'
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_diffrn_measured_fraction_theta_max 0.983
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_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  0.1607
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_Laue_measured_fraction_full 0.983
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_diffrn_reflns_point_group_measured_fraction_full 0.983
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_diffrn_reflns_theta_full        25.207
_diffrn_reflns_theta_max         25.207
_diffrn_reflns_theta_min         2.649
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_exptl_absorpt_correction_T_min  0.983
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_exptl_crystal_colour            orange
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_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
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_refine_diff_density_min         -0.169
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_refine_ls_extinction_coef       0.0025(5)
_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   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0624
_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^)+(0.0618P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1261
_reflns_number_total             2647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02823_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_Hall     '-C 2yn'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4034272
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              63740
_shelx_hkl_checksum              97911