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_7160239
_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 Br N2 O2'
_chemical_formula_sum            'C14 H17 Br N2 O2'
_chemical_formula_weight         325.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 100.3895(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.54497(6)
_cell_length_b                   7.19449(4)
_cell_length_c                   18.56940(11)
_cell_measurement_reflns_used    17234
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.5240
_cell_measurement_theta_min      4.4980
_cell_volume                     1385.683(14)
_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      99.98(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 0.998
_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    -27.00  33.00   0.50    0.05    --  -44.88  19.00-180.00  120
  2  \w    -51.00 -20.00   0.50    0.12    --  -93.75  45.00-180.00   62
  3  \w    -85.00 -23.00   0.50    0.12    --  -93.75 125.00 120.00  124
  4  \w    -37.00  31.00   0.50    0.05    --  -44.88  32.00  27.00  136
  5  \w    -37.00  31.00   0.50    0.05    --  -44.88  32.00  27.00  136
  6  \w    -32.00  27.00   0.50    0.05    --   44.88 -19.00 120.00  118
  7  \w     43.00 105.00   0.50    0.12    --  115.25 -95.00-120.00  124
  8  \w     45.00 111.00   0.50    0.12    --  115.25-125.00-180.00  132
  9  \w     45.00 111.00   0.50    0.12    --  115.25-125.00-150.00  132
 10  \w    -31.00  37.00   0.50    0.05    --   44.88 -32.00-131.00  136
 11  \w     44.00  70.00   0.50    0.12    --  115.25 -95.00 -90.00   52
 12  \w     43.00 105.00   0.50    0.12    --  115.25 -95.00   0.00  124
 13  \w     44.00  98.00   0.50    0.12    --  115.25 -84.00  92.43  108
 14  \w     43.00 105.00   0.50    0.12    --  115.25 -95.00 120.00  124
 15  \w    104.00 141.00   0.50    0.12    --  115.25 -84.00  92.43   74
 16  \w     43.00 144.00   0.50    0.12    --  115.25 -83.00 -44.06  202
 17  \w     95.00 178.00   0.50    0.12    --  115.25 125.00 150.00  166
 18  \w     43.00  68.00   0.50    0.12    --  115.25 -61.00  30.00   50
 19  \w     43.00 105.00   0.50    0.12    --  115.25 -77.00 -90.00  124
 20  \w     43.00 110.00   0.50    0.12    --  115.25 -78.00-113.89  134
 21  \w     43.00  71.00   0.50    0.12    --  115.25 -61.00 -90.00   56
 22  \w     46.00  82.00   0.50    0.12    --  115.25 -77.00 -60.00   72
 23  \w     43.00 105.00   0.50    0.12    --  115.25 -77.00   0.00  124
 24  \w     43.00 105.00   0.50    0.12    --  115.25 -77.00  60.00  124
 25  \w     43.00 105.00   0.50    0.12    --  115.25 -77.00 150.00  124
 26  \w     43.00  71.00   0.50    0.12    --  115.25 -61.00-120.00   56
 27  \w     44.00  70.00   0.50    0.12    --  115.25 -61.00-180.00   52
 28  \w    142.00 170.00   0.50    0.12    --  115.25   0.00-150.00   56
 29  \w     89.00 178.00   0.50    0.12    --  115.25  77.00  90.00  178
 30  \w     89.00 178.00   0.50    0.12    --  115.25  77.00 120.00  178
 31  \w     90.00 115.00   0.50    0.12    --  115.25  77.00 120.00   50
 32  \w     96.00 162.00   0.50    0.12    --  115.25  61.00 120.00  132
 33  \w     96.00 162.00   0.50    0.12    --  115.25  61.00 120.00  132
 34  \w     97.00 178.00   0.50    0.12    --  115.25  45.00 150.00  162
 35  \w     97.00 178.00   0.50    0.12    --  115.25  45.00  90.00  162
 36  \w     27.00 121.00   0.50    0.05    --   44.88  32.00  27.00  188
 37  \w     97.00 178.00   0.50    0.12    --  115.25  32.00  27.00  162
 38  \w     97.00 178.00   0.50    0.12    --  115.25  45.00 -30.00  162
 39  \w     97.00 178.00   0.50    0.12    --  115.25  30.00 -60.00  162
 40  \w     96.00 178.00   0.50    0.12    --  115.25  61.00-150.00  164
 41  \w     97.00 178.00   0.50    0.12    --  115.25  45.00-120.00  162
 42  \w     46.00  72.00   0.50    0.12    --  115.25   0.00-150.00   52
 43  \w   -121.00 -27.00   0.50    0.05    --  -44.88 -32.00-131.00  188
 44  \w   -170.00 -76.00   0.50    0.12    --  -93.75 -32.00-131.00  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      -0.1238331000
_diffrn_orient_matrix_UB_12      0.0544993000
_diffrn_orient_matrix_UB_13      -0.0533302000
_diffrn_orient_matrix_UB_21      0.0596844000
_diffrn_orient_matrix_UB_22      -0.0704763000
_diffrn_orient_matrix_UB_23      -0.0648008000
_diffrn_orient_matrix_UB_31      -0.0562572000
_diffrn_orient_matrix_UB_32      -0.1946726000
_diffrn_orient_matrix_UB_33      0.0085290000
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.048
_diffrn_reflns_theta_min         4.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.048
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.426
_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    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00080(12)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0307P)^2^+1.6140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3017
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01570c2.cif
_cod_data_source_block           13r-450-prld
_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_original_cell_volume        1385.683(13)
_cod_database_code               7160239
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C14H1702BrN2
_chemical_oxdiff_usercomment     13R-450-PRLD
_shelx_estimated_absorpt_t_max   0.642
_shelx_estimated_absorpt_t_min   0.142
_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:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b 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              62989
_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 1.762
_oxdiff_exptl_absorpt_empirical_full_min 0.820