The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine 1,4-dioxides.
Bakuleva, Nadezhda A.; Lichitskii, Boris V.; Komogortsev, Andrey N.; Tretyakov, Evgeny V.; Organic & biomolecular chemistry 23 (2025) 369–376; doi:10.1039/d4ob01570c

data_7160240
_publ_section_title
;
 The study of the photochemical behavior of 5-aryl-2,3-dihydropyrazine
 1,4-dioxides.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              369
_journal_page_last               376
_journal_paper_doi               10.1039/d4ob01570c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C14 H17 Cl N2 O2'
_chemical_formula_sum            'C14 H17 Cl N2 O2'
_chemical_formula_weight         280.74
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-02-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.1830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.58470(10)
_cell_length_b                   11.18550(10)
_cell_length_c                   13.06700(10)
_cell_measurement_reflns_used    18468
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.6560
_cell_measurement_theta_min      3.8730
_cell_volume                     1369.36(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -51.00 -20.00   0.50    0.32    --  -93.75  45.00 -90.00   62
  2  \w    -71.00 -20.00   0.50    0.32    --  -93.75  61.00 -60.00  102
  3  \w    -51.00 -20.00   0.50    0.32    --  -93.75  45.00 120.00   62
  4  \w    -47.00 -19.00   0.50    0.32    --  -93.75  42.00 131.00   56
  5  \w    -47.00  30.00   0.50    0.08    --  -44.88  42.00 131.00  154
  6  \w    -47.00  30.00   0.50    0.08    --  -44.88  42.00 131.00  154
  7  \w    -32.00  27.00   0.50    0.08    --   44.88 -19.00-150.00  118
  8  \w     95.00 178.00   0.50    0.32    --  115.25 125.00 120.00  166
  9  \w     16.00  43.00   0.50    0.08    --   44.88  85.00-137.78   54
 10  \w    -29.00  47.00   0.50    0.08    --   44.88 -42.00 -20.00  152
 11  \w     92.00 118.00   0.50    0.32    --  115.25  77.00 120.00   52
 12  \w    139.00 178.00   0.50    0.32    --  115.25  77.00 150.00   78
 13  \w    144.00 170.00   0.50    0.32    --  115.25  77.00  30.00   52
 14  \w     96.00 178.00   0.50    0.32    --  115.25  61.00 -30.00  164
 15  \w     96.00 178.00   0.50    0.32    --  115.25  61.00 -30.00  164
 16  \w     97.00 178.00   0.50    0.32    --  115.25  42.00 131.00  162
 17  \w     89.00 130.00   0.50    0.32    --  115.25  77.00 -60.00   82
 18  \w     96.00 172.00   0.50    0.32    --  115.25  61.00 -90.00  152
 19  \w     96.00 178.00   0.50    0.32    --  115.25  61.00-150.00  164
 20  \w     97.00 178.00   0.50    0.32    --  115.25  45.00-180.00  162
 21  \w     97.00 178.00   0.50    0.32    --  115.25  30.00-150.00  162
 22  \w     97.00 178.00   0.50    0.32    --  115.25  30.00 -90.00  162
 23  \w    147.00 173.00   0.50    0.32    --  115.25  15.00-150.00   52
 24  \w    137.00 176.00   0.50    0.32    --  115.25  15.00 -60.00   78
 25  \w     90.00 178.00   0.50    0.32    --  115.25  15.00 -30.00  176
 26  \w     27.00 119.00   0.50    0.08    --   44.88  42.00 131.00  184
 27  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00-120.00  124
 28  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00-150.00  124
 29  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00 -90.00  124
 30  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00  30.00  124
 31  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00  30.00  124
 32  \w     43.00  71.00   0.50    0.32    --  115.25 -61.00-150.00   56
 33  \w     43.00  71.00   0.50    0.32    --  115.25 -61.00  30.00   56
 34  \w     48.00  73.00   0.50    0.32    --  115.25 -77.00  60.00   50
 35  \w     43.00  71.00   0.50    0.32    --  115.25 -61.00  60.00   56
 36  \w     43.00 105.00   0.50    0.32    --  115.25 -77.00  90.00  124
 37  \w    110.00 144.00   0.50    0.32    --  115.25 -84.00 127.65   68
 38  \w     45.00 111.00   0.50    0.32    --  115.25-125.00 150.00  132
 39  \w     45.00 111.00   0.50    0.32    --  115.25-125.00  60.00  132
 40  \w     71.00 103.00   0.50    0.32    --  115.25 -95.00  30.00   64
 41  \w     65.00  91.00   0.50    0.32    --  115.25-125.00 -60.00   52
 42  \w     34.00  94.00   0.50    0.08    --   44.88-125.00-180.00  120
 43  \w     54.00  80.00   0.50    0.32    --  115.25 -95.00-120.00   52
 44  \w    109.00 141.00   0.50    0.32    --  115.25 -88.00-167.37   64
 45  \w     46.00  71.00   0.50    0.32    --  115.25 -88.00-167.37   50
 46  \w     86.00 111.00   0.50    0.32    --  115.25-125.00 -90.00   50
 47  \w     49.00  75.00   0.50    0.32    --  115.25 -95.00 120.00   52
 48  \w     43.00 105.00   0.50    0.32    --  115.25 -95.00 150.00  124
 49  \w   -119.00 -26.00   0.50    0.08    --  -44.88 -42.00 -20.00  186
 50  \w   -168.00 -74.00   0.50    0.32    --  -93.75 -42.00 -20.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1172756000
_diffrn_orient_matrix_UB_12      -0.0406795000
_diffrn_orient_matrix_UB_13      0.0930818000
_diffrn_orient_matrix_UB_21      0.0806882000
_diffrn_orient_matrix_UB_22      -0.0601939000
_diffrn_orient_matrix_UB_23      -0.0764282000
_diffrn_orient_matrix_UB_31      0.0822126000
_diffrn_orient_matrix_UB_32      0.1170010000
_diffrn_orient_matrix_UB_33      -0.0069775000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.911
_diffrn_reflns_theta_min         4.720
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.6551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01570c2.cif
_cod_data_source_block           cl450
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160239--7160242.cif.
;
_cod_database_code               7160240
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H1707ClN2
_chemical_oxdiff_usercomment     CL450
_shelx_estimated_absorpt_t_max   0.612
_shelx_estimated_absorpt_t_min   0.236
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              27907
_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 1.840
_oxdiff_exptl_absorpt_empirical_full_min 0.745