Electrochemical synthesis of alpha-enaminones from aryl ketones
Yanan Li; Huihui Gao; Zhenlei Zhang; Peng Qian; Meixiang Bi; Zhenggen Zha; Zhiyong Wang; Chem.Commun. 52 (2016) 8600–; doi:

data_7119833
_publ_section_title
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 Electrochemical synthesis of alpha-enaminones from aryl ketones
;
_journal_name_full               Chem.Commun.
_journal_page_first              8600
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_chemical_melting_point          417.5(5)
_chemical_name_systematic
'(E)-ethyl 4-(naphthalen-2-yl)-2-nitro-4-oxo-3-(piperidin-1-yl)but-2-enoate'
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-04-14 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.003(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2787(9)
_cell_length_b                   9.4954(4)
_cell_length_c                   14.5637(8)
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      22.7070
_cell_measurement_theta_min      3.5580
_cell_volume                     1955.34(18)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11149
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.548
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ' yellow '
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0945P)^2^+0.8826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.2113
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2582
_reflns_number_total             3993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03709g2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '417-418' was changed to '417.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_database_code               7119833
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2013-4
_shelx_res_checksum              22497
_shelx_hkl_checksum              33529
_solvent_exptl_crystal_recrystallization_method ' acetone/petroleum ether'