Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes.
Hossain, Mohammad Lokman; Ye, Fei; Liu, Zhenxing; Xia, Ying; Shi, Yi; Zhou, Lei; Zhang, Yan; Wang, Jianbo; The Journal of organic chemistry 79 (2014) 8689–8699; doi:10.1021/jo501489c

data_4029909
_publ_section_title
;
 Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of
 N-Tosylhydrazones with Terminal Alkynes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8689
_journal_page_last               8699
_journal_paper_doi               10.1021/jo501489c
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C22 H18 S'
_chemical_formula_sum            'C22 H18 S'
_chemical_formula_weight         314.42
_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
_audit_creation_date             2014-07-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                96.964(5)
_cell_angle_beta                 103.030(6)
_cell_angle_gamma                90.128(4)
_cell_formula_units_Z            4
_cell_length_a                   10.5531(5)
_cell_length_b                   12.5597(5)
_cell_length_c                   12.6208(11)
_cell_measurement_reflns_used    3879
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.6840
_cell_measurement_theta_min      3.4080
_cell_volume                     1616.96(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9945
_diffrn_measured_fraction_theta_max 0.8181
_diffrn_measurement_details
;
  1 omega  -33.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -89.0000   21.0000 82

  2 omega  -47.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -57.0000 -120.0000 87

  3 omega  -18.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   77.0000  150.0000 103
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0003933000
_diffrn_orient_matrix_UB_12      0.0098579000
_diffrn_orient_matrix_UB_13      0.0564633000
_diffrn_orient_matrix_UB_21      -0.0279699000
_diffrn_orient_matrix_UB_22      0.0504964000
_diffrn_orient_matrix_UB_23      -0.0082192000
_diffrn_orient_matrix_UB_31      -0.0630989000
_diffrn_orient_matrix_UB_32      -0.0243493000
_diffrn_orient_matrix_UB_33      -0.0111719000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10534
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description
;
;
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0199(15)
_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   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0638
_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
'w=1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.2405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4761
_reflns_number_total             6338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo501489c_si_001.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 4029909.cif.'
_cod_database_code               4029909
_chemical_oxdiff_formula         'C15 H15 S1'
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C38(H38A,H38B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30), C33(H33), C35(H35), C36(H36), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C37(H37A,H37B,H37C)
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.962
_shelxl_version_number           2013-3