Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate
Andria M. Panagopoulos; Doug Steinman; Alexandra Goncharenko; Kyle Geary; Carlene Schleisman; Elizabeth Spaargaren; Matthias Zeller; Daniel P. Becker; Journal of Organic Chemistry 78 (2013) 3532–3540; doi:10.1021/jo302795w

data_4028136
_publ_section_title
;
 Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3532
_journal_page_last               3540
_journal_paper_doi               10.1021/jo302795w
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H20 N3, C7 H7 O3 S'
_chemical_formula_sum            'C27 H27 N3 O3 S'
_chemical_formula_weight         473.59
_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                 92.7970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9118(8)
_cell_length_b                   10.1696(7)
_cell_length_c                   17.7957(12)
_cell_measurement_reflns_used    3836
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.29
_cell_volume                     2333.9(3)
_computing_cell_refinement       'SAINT+ 6.45 (Bruker, 2003)'
_computing_data_collection       'SMART 5.630 (Bruker, 1997-2002)'
_computing_data_reduction        'SAINT+ 6.45'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_structure_solution
; 
SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w 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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13089
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0506P)^2^+0.8255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                4645
_reflns_number_total             5758
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo302795w_si_002_1.cif
_cod_data_source_block           5a-tosylate-salt
_cod_database_code               4028136