UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides.
Chen, Ming; Yang, Chao; Wang, Yanpei; Li, Dazhi; Xia, Wujiong; Organic letters 18 (2016) 2280–2283; doi:10.1021/acs.orglett.6b00878

data_1543162
_publ_section_title
;
 UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a
 Linear 3-Aryl-N-(arylsulfonyl) Propiolamides.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2280
_journal_page_last               2283
_journal_paper_doi               10.1021/acs.orglett.6b00878
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C17 H13 N O3 S'
_chemical_formula_sum            'C17 H13 N O3 S'
_chemical_formula_weight         311.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
_cell_angle_beta                 108.6465(18)
_cell_angle_gamma                90
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_cell_length_a                   21.2968(3)
_cell_length_b                   7.11439(11)
_cell_length_c                   21.9163(4)
_cell_measurement_reflns_used    3691
_cell_measurement_temperature    293(2)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
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_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -22.00    5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 27

  2 omega  -14.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 61

  3 omega   67.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 56

  4 omega   87.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 79

  5 omega  113.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 62

  6 omega  108.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   90.0000 61

  7 omega   52.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -134.0000   87.0000 26

  8 omega   41.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 70

  9 omega   47.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   60.0000 45

 10 omega   45.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 90

 11 omega   47.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -120.0000 45

 12 omega   86.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 27

 13 omega   27.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 74

 14 omega   36.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000    0.0000 55

 15 omega   42.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 74

 16 omega  -15.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 85

 17 omega  -55.00    1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  119.0000   73.0000 56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0126052000
_diffrn_orient_matrix_UB_12      -0.1118442000
_diffrn_orient_matrix_UB_13      0.0629759000
_diffrn_orient_matrix_UB_21      0.0069867000
_diffrn_orient_matrix_UB_22      0.1854146000
_diffrn_orient_matrix_UB_23      0.0379128000
_diffrn_orient_matrix_UB_31      -0.0749704000
_diffrn_orient_matrix_UB_32      -0.0015715000
_diffrn_orient_matrix_UB_33      -0.0100313000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_number            5604
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.258
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.930
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_exptl_absorpt_correction_type   multi-scan
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description
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;
_exptl_crystal_F_000             1296
_platon_squeeze_details
;
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.0207P] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00878_si_002.cif
_cod_data_source_block           20141126xia
_cod_depositor_comments
'Adding full bibliography for 1543162--1543163.cif.'
_cod_original_cell_volume        3146.31(9)
_cod_database_code               1543162
_reflns_odcompleteness_completeness 99.89
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C29(H29), C31(H31), C32(H32), C34(H34), C2(H2),
 C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C33(H33A,H33B,H33C), C10(H10A,H10B,H10C), C17(H17A,H17B,
 H17C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'