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_4028817
_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 H9 Cl N2 O'
_chemical_formula_sum            'C11 H9 Cl N2 O'
_chemical_formula_weight         220.65
_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                 98.57
_cell_angle_gamma                90.00
_cell_formula_units_Z            20
_cell_length_a                   18.014
_cell_length_b                   11.966
_cell_length_c                   25.055
_cell_measurement_reflns_used    1067
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.17
_cell_measurement_theta_min      3.41
_cell_volume                     5340.442
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1262
_diffrn_reflns_av_sigmaI/netI    0.1408
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30830
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         9425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.2317
_refine_ls_R_factor_gt           0.1139
_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^)+(0.0998P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2881
_reflns_number_gt                3942
_reflns_number_total             9425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401997v_si_002.cif
_cod_data_source_block           xxq
_cod_original_cell_volume        5340.6
_cod_database_code               4028817