Photochemical electrocyclic ring closure and leaving group expulsion from N-(9-oxothioxanthenyl)benzothiophene carboxamides.
Sarker, Majher I.; Shahrin, Tasnuva; Steinmetz, Mark G.; Timerghazin, Qadir K.; Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 12 (2013) 309–322; doi:10.1039/c2pp25051a

data_1514874
_publ_section_title
;
 Photochemical electrocyclic ring closure and leaving group expulsion from
 N-(9-oxothioxanthenyl)benzothiophene carboxamides.
;
_journal_issue                   2
_journal_name_full
'Photochemical &amp; photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              309
_journal_page_last               322
_journal_paper_doi               10.1039/c2pp25051a
_journal_volume                  12
_journal_year                    2013
_chemical_formula_moiety         'C23 H13 N O2 S2'
_chemical_formula_sum            'C23 H13 N O2 S2'
_chemical_formula_weight         399.46
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-23
_audit_creation_method
;
Olex2 1.1-beta
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.870(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1311(2)
_cell_length_b                   15.2998(4)
_cell_length_c                   14.1896(4)
_cell_measurement_reflns_used    5901
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7331
_cell_measurement_theta_min      4.3258
_cell_volume                     1706.13(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
;
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
1 omega -46.00 32.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- -40.6694 37.0000 -30.0000 78

2 omega -37.00 24.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- -40.6694 37.0000 -150.0000 61

3 omega 28.00 63.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 40.6694 -125.0000 90.0000 35

4 omega 34.00 88.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 40.6694 -125.0000 -30.0000 54

5 omega 106.00 177.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 30.0000 -180.0000 71

6 omega 34.00 60.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -30.0000 120.0000 26

7 omega 42.00 89.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -45.0000 150.0000 47

8 omega 35.00 75.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -30.0000 -150.0000 40

9 omega 124.00 162.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 125.0000 150.0000 38

10 omega 45.00 90.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -30.0000 60.0000 45

11 omega 33.00 86.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -30.0000 -90.0000 53

12 omega 98.00 178.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 45.0000 -120.0000 80

13 omega 60.00 91.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -30.0000 -30.0000 31

14 omega -119.00 -7.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- -40.6694 -77.0000 -150.0000 112

15 omega 14.00 117.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 40.6694 37.0000 -30.0000 103

16 omega 11.00 115.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 40.6694 58.0000 51.0000 104

17 omega 79.00 178.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 45.0000 -30.0000 99

18 omega 32.00 121.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -125.0000 150.0000 89

19 omega 23.00 109.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 -94.0000 -90.0000 86

20 omega 77.00 178.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 61.0000 -150.0000 101

21 omega 77.00 178.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 61.0000 0.0000 101

22 omega 46.00 178.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 107.0171 15.0000 120.0000 132

23 omega 7.00 98.00 1.0000 8.0000
omega____ theta____ kappa____ phi______ frames
- 40.6694 77.0000 120.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1358512000
_diffrn_orient_matrix_UB_12      0.0659409000
_diffrn_orient_matrix_UB_13      0.0127828000
_diffrn_orient_matrix_UB_21      0.1094406000
_diffrn_orient_matrix_UB_22      0.0223818000
_diffrn_orient_matrix_UB_23      0.1029197000
_diffrn_orient_matrix_UB_31      0.0893969000
_diffrn_orient_matrix_UB_32      0.0727205000
_diffrn_orient_matrix_UB_33      -0.0432263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16706
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         73.90
_diffrn_reflns_theta_min         4.33
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0484P)^2^+0.7672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                2948
_reflns_number_total             3400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2pp25051a.txt
_cod_data_source_block           steinv
_cod_original_cell_volume        1706.14(8)
_cod_database_code               1514874
_chemical_oxdiff_formula         'C23 H13 O2 N S2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97