One-pot synthesis and crystal structure of diethyl 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate, C21H23N5O6
Konovalova, Irina S.; Geleverya, Anna O.; Kovalenko, Sergiy M.; Reiss, Guido J.; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 381–384; doi:10.1515/ncrs-2022-0573

data_8107447
_publ_section_title
;
 One-pot synthesis and crystal structure of diethyl
 2,6-dimethyl-4-(1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate,
 C21H23N5O6
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              381
_journal_page_last               384
_journal_paper_doi               10.1515/ncrs-2022-0573
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C21 H23 N5 O6'
_chemical_formula_sum            'C21 H23 N5 O6'
_chemical_formula_weight         441.44
_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                 97.605(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4861(4)
_cell_length_b                   16.3198(8)
_cell_length_c                   15.8521(8)
_cell_measurement_reflns_used    6865
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.9360
_cell_measurement_theta_min      3.5970
_cell_volume                     2176.07(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2678
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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    -45.00  50.00   1.00    4.00    --   26.66 -48.00 -34.00   95
  2  \w      3.00  98.00   1.00    4.00    --   26.66  48.00 113.00   95
  3  \w    -99.00  -4.00   1.00    4.00    --  -27.91 -48.00 -34.00   95
  4  \w    -51.00  43.00   1.00    4.00    --  -27.91  48.00 113.00   94
  5  \w    -25.00  70.00   1.00    4.00    --   26.66 -99.00  60.00   95
  6  \w     32.00 105.00   1.00    4.00    --   26.66-178.00-120.00   73
  7  \w    -25.00  70.00   1.00    4.00    --   26.66 -99.00 -60.00   95
  8  \w    -44.00  58.00   1.00    4.00    --   26.66 -77.00 150.00  102
  9  \w      5.00  96.00   1.00    4.00    --   26.66  57.00-120.00   91
 10  \w    -99.00 -49.00   1.00    4.00    --  -27.91 -77.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0736865000
_diffrn_orient_matrix_UB_12      0.0206355000
_diffrn_orient_matrix_UB_13      -0.0101207000
_diffrn_orient_matrix_UB_21      0.0264294000
_diffrn_orient_matrix_UB_22      0.0163267000
_diffrn_orient_matrix_UB_23      -0.0371185000
_diffrn_orient_matrix_UB_31      -0.0314470000
_diffrn_orient_matrix_UB_32      -0.0345910000
_diffrn_orient_matrix_UB_33      -0.0235842000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29778
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.479
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.633
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.316
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+1.2530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2949
_reflns_number_total             3818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0573_suppl.cif
_cod_data_source_block           irinak001rt
_cod_database_code               8107447
_chemical_oxdiff_formula         'C21H23 O6 Cl N5'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C1(H1), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.725