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_7160241
_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         'C16 H22 N2 O4'
_chemical_formula_sum            'C16 H22 N2 O4'
_chemical_formula_weight         306.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-02-15
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.76900(10)
_cell_length_b                   12.7670(2)
_cell_length_c                   22.6802(3)
_cell_measurement_reflns_used    12356
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.5840
_cell_measurement_theta_min      3.8700
_cell_volume                     3118.25(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.996
_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    -54.00 -29.00   0.50    1.50    --  -44.25  95.00  -4.00   50
  2  \w     -7.00  30.00   0.50    1.50    --  -44.25  46.00 139.00   74
  3  \w     27.00  65.00   0.50    1.50    --   44.25 -88.00 140.00   76
  4  \w   -152.00-127.00   0.50    6.00    --  -96.00 -46.00 -10.00   50
  5  \w   -159.00-134.00   0.50    6.00    --  -96.00 -88.00 140.00   50
  6  \w   -160.00-135.00   0.50    6.00    --  -96.00 -95.00-115.00   50
  7  \w     46.00  91.00   0.50    6.00    --  117.50 -88.00 140.00   90
  8  \w     45.00  84.00   0.50    6.00    --  117.50 -95.00-115.00   78
  9  \w    109.00 176.00   0.50    6.00    --  117.50  46.00 139.00  134
 10  \w    137.00 170.00   0.50    6.00    --  117.50  95.00  -4.00   66
 11  \w    -11.00  32.00   0.50    1.50    --  -44.25  38.00-120.00   86
 12  \w   -110.00 -64.00   0.50    1.50    --  -44.25 -38.00  30.00   92
 13  \w      7.00  65.00   0.50    1.50    --   44.25 -77.00  30.00  116
 14  \w    109.00 134.00   0.50    6.00    --  117.50  15.00 120.00   50
 15  \w    109.00 134.00   0.50    6.00    --  117.50  15.00-120.00   50
 16  \w    110.00 136.00   0.50    6.00    --  117.50  15.00   0.00   52
 17  \w     45.00  70.00   0.50    6.00    --  117.50 -77.00-120.00   50
 18  \w     47.00  73.00   0.50    6.00    --  117.50-125.00-150.00   52
 19  \w     53.00  88.00   0.50    6.00    --  117.50 -95.00 -60.00   70
 20  \w     47.00  74.00   0.50    6.00    --  117.50 -77.00-180.00   54
 21  \w    146.00 174.00   0.50    6.00    --  117.50  77.00 -30.00   56
 22  \w     51.00  76.00   0.50    6.00    --  117.50 -95.00 -90.00   50
 23  \w    112.00 155.00   0.50    6.00    --  117.50  30.00 -90.00   86
 24  \w     46.00  74.00   0.50    6.00    --  117.50 -95.00  30.00   56
 25  \w    129.00 178.00   0.50    6.00    --  117.50  77.00-120.00   98
 26  \w    109.00 134.00   0.50    6.00    --  117.50  15.00 -90.00   50
 27  \w    112.00 160.00   0.50    6.00    --  117.50 125.00 120.00   96
 28  \w     47.00  72.00   0.50    6.00    --  117.50 -77.00 120.00   50
 29  \w     45.00  70.00   0.50    6.00    --  117.50 -77.00 150.00   50
 30  \w    119.00 178.00   0.50    6.00    --  117.50 125.00  90.00  118
 31  \w    117.00 142.00   0.50    6.00    --  117.50  61.00  30.00   50
 32  \w    111.00 147.00   0.50    6.00    --  117.50  45.00-120.00   72
 33  \w     47.00  72.00   0.50    6.00    --  117.50 -77.00 -90.00   50
 34  \w     66.00  91.00   0.50    6.00    --  117.50 -95.00-180.00   50
 35  \w    130.00 156.00   0.50    6.00    --  117.50 125.00 -30.00   52
 36  \w     50.00  75.00   0.50    6.00    --  117.50 -77.00 -60.00   50
;
_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      -0.0349693000
_diffrn_orient_matrix_UB_12      0.1025948000
_diffrn_orient_matrix_UB_13      -0.0316378000
_diffrn_orient_matrix_UB_21      -0.0741399000
_diffrn_orient_matrix_UB_22      0.0351818000
_diffrn_orient_matrix_UB_23      0.0546044000
_diffrn_orient_matrix_UB_31      0.1171901000
_diffrn_orient_matrix_UB_32      0.0529037000
_diffrn_orient_matrix_UB_33      0.0251680000
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20617
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.784
_diffrn_reflns_theta_min         3.898
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0432P)^2^+1.1456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3126
_reflns_number_total             3415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01570c2.cif
_cod_data_source_block           nb-168ph
_cod_depositor_comments
'Adding full bibliography for 7160239--7160242.cif.'
_cod_database_code               7160241
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C16H22O4N2
_chemical_oxdiff_usercomment     NB-164PH
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.927
_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:
 C10(H10), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,
 H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              51614
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.723