Deciphering the Mechanistic Dichotomy in the Cyclization of 1-(2-Ethynylphenyl)-3,3-dialkyltriazenes: Competition between Pericyclic and Pseudocoarctate Pathways
David B. Kimball; Timothy J. R. Weakley; Rainer Herges; Michael M. Haley; Journal of the American Chemical Society 124 (2002) 13463–13473; doi:10.1021/ja027809r

data_4115282
_publ_contact_author_address
;Department of Chemistry,
University of Oregon,
Eugene, OR 97403-1253
USA
;
_publ_contact_author_email       tweakley@oregon.uoregon.edu
_publ_contact_author_fax         01(541)3464643
_publ_contact_author_name        'Dr Timothy J. R. Weakley'
_publ_contact_author_phone       01(541)3464620
_publ_section_title
;
 Deciphering the Mechanistic Dichotomy in the Cyclization of
 1-(2-Ethynylphenyl)-3,3-dialkyltriazenes: Competition between Pericyclic
 and Pseudocoarctate Pathways
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13463
_journal_page_last               13473
_journal_paper_doi               10.1021/ja027809r
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C25 H25 N3 '
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.49
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2001-02-13
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90
_cell_angle_beta                 100.59(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.503(2)
_cell_length_b                   14.849(2)
_cell_length_c                   16.740(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      11.3
_cell_volume                     2077.6(6)
_computing_cell_refinement       'CAD4/PC (Enraf-Nonius, 1993)'
_computing_data_collection       'CAD4/PC (Enraf-Nonius, 1993)'
_computing_data_reduction        'TEXSAN (Molecular Structure Corp., 1997)'
_computing_publication_material  'TEXSAN (Molecular Structure Corp., 1997)'
_computing_structure_refinement  'TEXSAN (Molecular Structure Corp., 1997)'
_computing_structure_solution    'TEXSAN (Molecular Structure Corp., 1997)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device_type  'Nonius CAD-4 serial diffractometer'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      0.03341
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_diffrn_orient_matrix_UB_13      -0.00569
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_diffrn_orient_matrix_UB_33      0.02516
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.120
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_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_reduction_process 'Lp corrections applied'
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_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 300
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_exptl_absorpt_coefficient_mu    0.070
_exptl_crystal_colour            yellow
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_exptl_crystal_description       prism
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_refine_diff_density_max         0.53
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details 'not applicable'
_refine_ls_extinction_coef       0.00000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.61
_refine_ls_goodness_of_fit_ref   2.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
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_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.116
_refine_ls_R_factor_gt           0.080
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4F~o~^2^/[\s^2^(I) + (0.020I)^2^]'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.068
_reflns_number_gt                1885
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_reflns_threshold_expression     I>1.00\s(I)
_cod_data_source_file            ja027809r-2_s2_2.cif
_cod_data_source_block           DKIM0801_C25H25N3
_cod_original_cell_volume        2077.5(7)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C25 H25 N3 '
_cod_database_code               4115282