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_1543163
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H10 F N O3 S'
_chemical_formula_sum            'C16 H10 F N O3 S'
_chemical_formula_weight         315.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.893(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8436(5)
_cell_length_b                   10.3886(6)
_cell_length_c                   9.9058(6)
_cell_measurement_reflns_used    1199
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5390
_cell_measurement_theta_min      3.9140
_cell_volume                     680.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

--------------------------------------------------------------------------
  1  \w     -3.00  88.00   1.00    9.00    --   18.81  57.00 150.00   91
  2  \w     -9.00  56.00   1.00    9.00    --   18.81  37.00 120.00   65
  3  \w    -20.00   8.00   1.00    9.00    --   18.81 -99.00 -60.00   28
  4  \w    -51.00   3.00   1.00    9.00    --   18.81 -77.00-150.00   54
  5  \w    -13.00  12.00   1.00    9.00    --  -19.74 -77.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0821775000
_diffrn_orient_matrix_UB_12      0.0067860000
_diffrn_orient_matrix_UB_13      0.0309154000
_diffrn_orient_matrix_UB_21      0.0682422000
_diffrn_orient_matrix_UB_22      0.0180064000
_diffrn_orient_matrix_UB_23      0.0639794000
_diffrn_orient_matrix_UB_31      -0.0102845000
_diffrn_orient_matrix_UB_32      0.0654998000
_diffrn_orient_matrix_UB_33      -0.0208449000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3021
_diffrn_reflns_point_group_measured_fraction_full 0.754
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.335
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         3.080
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.84(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1875
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.2158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.428
_reflns_Friedel_fraction_full    0.481
_reflns_Friedel_fraction_max     0.481
_reflns_number_gt                1468
_reflns_number_total             1875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00878_si_003.cif
_cod_data_source_block           20151202-2
_cod_depositor_comments
'Adding full bibliography for 1543162--1543163.cif.'
_cod_database_code               1543163
_chemical_oxdiff_formula         'C H N O F S'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.757