Base-mediated synthesis of highly functionalized 2-aminonicotinonitriles from α-keto vinyl azides and α,α-dicyanoalkenes
Shu, Ke; Shao, Jiaan; Li, Hong; Chen, Binhui; Tang, Pai; Liu, Xingyu; Chen, Wenteng; Yu, Yongping; RSC Advances 6 (2016) 49123–; doi:10.1039/C6RA04669J

data_7236203
_publ_section_title
;
 Base-mediated synthesis of highly functionalized 2-aminonicotinonitriles
 from \a-keto vinyl azides and \a,\a-dicyanoalkenes
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              49123
_journal_paper_doi               10.1039/C6RA04669J
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C26 H18 Cl N3 O'
_chemical_formula_sum            'C26 H18 Cl N3 O'
_chemical_formula_weight         423.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-10-19 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.306(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1894(9)
_cell_length_b                   9.6526(7)
_cell_length_c                   20.0169(17)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4476
_cell_measurement_theta_min      3.0113
_cell_volume                     2222.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0135533000
_diffrn_orient_matrix_UB_12      0.0465427000
_diffrn_orient_matrix_UB_13      0.0290480000
_diffrn_orient_matrix_UB_21      -0.0107700000
_diffrn_orient_matrix_UB_22      0.0569120000
_diffrn_orient_matrix_UB_23      -0.0237697000
_diffrn_orient_matrix_UB_31      -0.0581339000
_diffrn_orient_matrix_UB_32      0.0003275000
_diffrn_orient_matrix_UB_33      0.0000974000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9063
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0502P)^2^+0.4135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2597
_reflns_number_total             4066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra04669j2.cif
_cod_data_source_block           150422_sk_150421
_cod_database_code               7236203
_chemical_oxdiff_formula         'c10 h10 n2 o8 Cl1'
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 H2B-N2
 0.85 with sigma of 0.02
3.a Rotating group:
 N2(H2A)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;