Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides
Xiaoqing Xin; Dexuan Xiang; Jiming Yang; Qian Zhang; Fenguo Zhou; Dewen Dong; Journal of Organic Chemistry 78 (2013) 11956–11961; doi:10.1021/jo401997v

data_4028818
_publ_section_title
;
 Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of
 Methylenemalononitriles to 2-Cyanoacrylamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11956
_journal_page_last               11961
_journal_paper_doi               10.1021/jo401997v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C11 H10 N2 O'
_chemical_formula_sum            'C11 H10 N2 O'
_chemical_formula_weight         186.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4278(11)
_cell_length_b                   10.9087(9)
_cell_length_c                   13.4767(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1946.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12108
_diffrn_reflns_theta_full        26.11
_diffrn_reflns_theta_max         26.11
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             858
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.4092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                3206
_reflns_number_total             3867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401997v_si_003.cif
_cod_data_source_block           x
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028818