Relay Catalysis by a Multifunctional Cu Catalyst in a Tandem Dehydro-/Dehalogenation Sequence along with N-Arylation.
Liang, Lei; Wang, Wei; Xu, Fengrong; Niu, Yan; Sun, Qi; Xu, Ping; Organic letters 15 (2013) 2770–2773; doi:10.1021/ol401105x

data_1512096
_publ_section_title
;
 Relay Catalysis by a Multifunctional Cu Catalyst in a Tandem
 Dehydro-/Dehalogenation Sequence along with N-Arylation.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2770
_journal_page_last               2773
_journal_paper_doi               10.1021/ol401105x
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C16 H10 Cl N3 O3'
_chemical_formula_sum            'C16 H10 Cl N3 O3'
_chemical_formula_weight         327.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Nov  5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                95.483(4)
_cell_angle_beta                 98.449(5)
_cell_angle_gamma                99.913(5)
_cell_formula_units_Z            4
_cell_length_a                   7.2229(4)
_cell_length_b                   13.4298(7)
_cell_length_c                   15.5038(8)
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      30.2398
_cell_measurement_theta_min      3.0974
_cell_volume                     1454.06(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9867
_diffrn_measured_fraction_theta_max 0.9820
_diffrn_measurement_details
;
  1 omega  -21.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7753  -98.0000 -177.0000 76

  2 omega  -87.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566  -57.0000  -90.0000 95

  3 omega  -44.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5566   57.0000   60.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0657143000
_diffrn_orient_matrix_UB_12      -0.0246945000
_diffrn_orient_matrix_UB_13      0.0245466000
_diffrn_orient_matrix_UB_21      0.0377062000
_diffrn_orient_matrix_UB_22      0.0375707000
_diffrn_orient_matrix_UB_23      0.0365867000
_diffrn_orient_matrix_UB_31      -0.0669464000
_diffrn_orient_matrix_UB_32      0.0299700000
_diffrn_orient_matrix_UB_33      -0.0152167000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8847
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.0658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                4492
_reflns_number_total             5679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401105x_si_001.cif
_cod_data_source_block           zm
_cod_original_cell_volume        1454.05(14)
_cod_database_code               1512096
_chemical_oxdiff_formula         'C21 H15 N3 O3 Cl'
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H19 of C19, H25 of C25, H24 of C24, H23 of C23, H22 of C22, H21 of C21, H13
  of C13, H9 of C9, H16 of C16, H15 of C15, H14 of C14, H30 of C30, H5 of C5,
  H8 of C8, H3 of C3, H6 of C6, H28 of C28, H7 of C7, H29 of C29, H31 of C31
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28),
  C29(H29), C30(H30), C31(H31)
;