The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
Tzvetkov, Nikolay T.; Peeva, Martina I.; Tsakovska, Ivanka; Milella, Luigi; Pajeva, Ilza; Stammler, Hans-Georg; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 319–321; doi:10.1515/ncrs-2022-0016

data_8105215
_publ_section_title
;
 The crystal structure of
 (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione,
 C15H16Cl2N4O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              319
_journal_page_last               321
_journal_paper_doi               10.1515/ncrs-2022-0016
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 Cl2 N4 O2'
_chemical_formula_sum            'C15 H16 Cl2 N4 O2'
_chemical_formula_weight         355.22
_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
_cell_angle_alpha                90
_cell_angle_beta                 109.217(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.2014(7)
_cell_length_b                   7.59320(10)
_cell_length_c                   17.9766(4)
_cell_measurement_reflns_used    19598
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      76.3120
_cell_measurement_theta_min      3.5320
_cell_volume                     3377.20(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL [3]'
_computing_structure_solution    'ShelXT [4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -59.00  26.00   1.00   10.00    --  -38.50  37.00 -90.00   85
  2  \w   -116.00 -15.00   1.00   10.00    --  -38.50 -19.00 -90.00  101
  3  \w    -59.00  33.00   1.00   10.00    --  -38.50  37.00  90.00   92
  4  \w    -84.00  -7.00   1.00   10.00    --  -38.50 125.00 -90.00   77
  5  \w     11.00  36.00   1.00   10.00    --   42.70  81.00-122.15   25
  6  \w     51.00 111.00   1.00   10.00    --   42.70  57.00 150.00   60
  7  \w     12.00  38.00   1.00   10.00    --   42.70  78.00 173.10   26
  8  \w     12.00  42.00   1.00   10.00    --   42.70  79.00   9.45   30
  9  \w     13.00  40.00   1.00   10.00    --   42.70  77.00  93.43   27
 10  \w     18.00  68.00   1.00   10.00    --   42.70  57.00  90.00   50
 11  \w     18.00  46.00   1.00   10.00    --   42.70  57.00 150.00   28
 12  \w     12.00  38.00   1.00   10.00    --   42.70  82.00 -43.45   26
 13  \w     16.00  70.00   1.00   10.00    --   42.70  67.00 -65.12   54
 14  \w     75.00 105.00   1.00   10.00    --   42.70  57.00  90.00   30
 15  \w     12.00  80.00   1.00   10.00    --   42.70 -99.00 150.00   68
 16  \w     18.00  68.00   1.00   10.00    --   42.70  57.00-120.00   50
 17  \w     85.00 114.00   1.00   10.00    --   42.70  37.00  60.00   29
 18  \w     23.00  76.00   1.00   10.00    --   42.70  37.00  60.00   53
 19  \w     85.00 120.00   1.00   40.00    --  111.00  61.00  90.00   35
 20  \w     32.00 107.00   1.00   40.00    --  111.00 -94.00  30.00   75
 21  \w     85.00 111.00   1.00   40.00    --  111.00  61.00 -65.34   26
 22  \w     89.00 124.00   1.00   40.00    --  111.00  45.00 -90.00   35
 23  \w     85.00 125.00   1.00   40.00    --  111.00  61.00 120.00   40
 24  \w     89.00 124.00   1.00   40.00    --  111.00  45.00 -60.00   35
 25  \w     85.00 111.00   1.00   40.00    --  111.00  61.00-159.21   26
 26  \w     44.00 133.00   1.00   40.00    --  111.00 -61.00  30.00   89
 27  \w     85.00 111.00   1.00   40.00    --  111.00  61.00   0.00   26
 28  \w     85.00 111.00   1.00   40.00    --  111.00  61.00  60.00   26
 29  \w    152.00 178.00   1.00   40.00    --  111.00  61.00  60.00   26
 30  \w     85.00 168.00   1.00   40.00    --  111.00  62.00 140.30   83
 31  \w     63.00 136.00   1.00   40.00    --  111.00 -61.00-150.00   73
 32  \w     89.00 144.00   1.00   40.00    --  111.00  45.00-180.00   55
 33  \w     89.00 115.00   1.00   40.00    --  111.00  45.00 120.00   26
 34  \w     85.00 111.00   1.00   40.00    --  111.00  61.00 -90.00   26
 35  \w     85.00 177.00   1.00   40.00    --  111.00  61.00-180.00   92
 36  \w    144.00 174.00   1.00   40.00    --  111.00  51.00  56.39   30
 37  \w     90.00 171.00   1.00   40.00    --  111.00  45.00   0.00   81
 38  \w    133.00 178.00   1.00   40.00    --  111.00  61.00-120.00   45
 39  \w     85.00 110.00   1.00   40.00    --  111.00  61.00-120.00   25
 40  \w    134.00 176.00   1.00   40.00    --  111.00  61.00 -90.00   42
 41  \w     85.00 113.00   1.00   40.00    --  111.00  61.00 150.00   28
 42  \w     89.00 123.00   1.00   40.00    --  111.00  45.00  90.00   34
 43  \w     86.00 115.00   1.00   40.00    --  111.00  58.00  16.31   29
 44  \w    132.00 178.00   1.00   40.00    --  111.00  61.00-150.00   46
 45  \w     41.00 112.00   1.00   40.00    --  111.00-125.00-150.00   71
 46  \w     41.00 113.00   1.00   40.00    --  111.00-125.00  30.00   72
 47  \w     85.00 111.00   1.00   40.00    --  111.00  61.00-150.00   26
 48  \w     85.00 111.00   1.00   40.00    --  111.00  61.00 -30.00   26
 49  \w     32.00 107.00   1.00   40.00    --  111.00 -94.00-120.00   75
 50  \w     89.00 122.00   1.00   40.00    --  111.00  45.00-120.00   33
 51  \w     89.00 155.00   1.00   40.00    --  111.00  45.00 -30.00   66
 52  \w     85.00 178.00   1.00   40.00    --  111.00  61.00  30.00   93
 53  \w    127.00 175.00   1.00   40.00    --  111.00  61.00  90.00   48
 54  \w    131.00 156.00   1.00   40.00    --  111.00  61.00 -65.34   25
 55  \w     41.00 112.00   1.00   40.00    --  111.00-125.00-120.00   71
 56  \w     87.00 113.00   1.00   40.00    --  111.00  51.00  56.39   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type       'CrysAlisPro convention [1]'
_diffrn_orient_matrix_UB_11      0.0053441000
_diffrn_orient_matrix_UB_12      0.1917497000
_diffrn_orient_matrix_UB_13      -0.0245162000
_diffrn_orient_matrix_UB_21      0.0126618000
_diffrn_orient_matrix_UB_22      0.0595368000
_diffrn_orient_matrix_UB_23      0.0861107000
_diffrn_orient_matrix_UB_31      0.0607142000
_diffrn_orient_matrix_UB_32      -0.0292668000
_diffrn_orient_matrix_UB_33      0.0147942000
_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  0.0443
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51349
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.586
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.023
_exptl_crystal_size_rad          0.104
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         8782
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      149.487
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0935P)^2^+0.2462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7282
_reflns_number_total             8782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0016_suppl.cif
_cod_data_source_block           ntz
_cod_database_code               8105215
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.577
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6481(13)
 0.3519(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C2 \\sim C5: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 1*[Sof(Cl1)+Sof(Cl3)+Sof(H13)+Sof(H15)+Sof(Cl21)+Sof(cl23)+Sof(H33)+Sof(H35)]=
 2 with esd of 0
 Sof(Cl3)=Sof(H13)=Sof(cl23)=Sof(H33)=1-FVAR(1)
 Sof(Cl1)=Sof(H15)=Sof(Cl21)=Sof(H35)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C22(H22A)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C30(H30A,H30B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C13(H13), C15(H15), C16(H16), N22(H22), C32(H32), C33(H33),
 C35(H35), C36(H36)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C25(H25A,H25B,H25C),
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;