A Unique Combined Source of "CN" from 1,2-Dichloroethane and TMSN3 in the Copper-Catalyzed Cyanation of a C(sp(3))-H Bond Adjacent to a Nitrogen Atom.
Zhang, Gen; Ma, Yunxia; Cheng, Guangbin; Liu, Dabin; Wang, Rui; Organic letters 16 (2014) 656–659; doi:10.1021/ol500045p

data_1513507
_publ_section_title
;
 A Unique Combined Source of &quot;CN&quot; from 1,2-Dichloroethane and
 TMSN3 in the Copper-Catalyzed Cyanation of a C(sp(3))-H Bond Adjacent to
 a Nitrogen Atom.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              656
_journal_page_last               659
_journal_paper_doi               10.1021/ol500045p
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.245(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0174(7)
_cell_length_b                   9.9046(9)
_cell_length_c                   14.5441(12)
_cell_measurement_reflns_used    1181
_cell_measurement_temperature    295.96(10)
_cell_measurement_theta_max      21.5380
_cell_measurement_theta_min      3.9700
_cell_volume                     1288.62(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295.96(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9846
_diffrn_measured_fraction_theta_max 0.5507
_diffrn_measurement_details
;
  1 omega  -48.00    0.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   38.0000  150.0000 32

  2 omega    1.00   26.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000  120.0000 17

  3 omega  -22.00   83.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -90.0000 70

  4 omega   50.00   87.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0251317000
_diffrn_orient_matrix_UB_12      -0.0148926000
_diffrn_orient_matrix_UB_13      0.0471166000
_diffrn_orient_matrix_UB_21      0.0012014000
_diffrn_orient_matrix_UB_22      -0.0698779000
_diffrn_orient_matrix_UB_23      -0.0106990000
_diffrn_orient_matrix_UB_31      0.0752173000
_diffrn_orient_matrix_UB_32      0.0060731000
_diffrn_orient_matrix_UB_33      -0.0090432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4420
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(5)
_refine_ls_extinction_coef       0.0068(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0413P)^2^+0.3856P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                2040
_reflns_number_total             3070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500045p_si_001.cif
_cod_data_source_block           zhangg0506
_cod_database_code               1513507
_reflns_odcompleteness_completeness 98.46
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C27(H27),
  C28(H28)
;