data_tz_247
_audit_creation_date               2022-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic         
 'methyl 6-benzyl-4-oxo-2-(p-tolyl)-1,4-dihydropyridine-3-carboxylate'
_chemical_formula_moiety           'C21 H19 N O3'
_chemical_formula_sum              'C21 H19 N O3'
_chemical_formula_weight           333.37
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C21 H19 N O3 '
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     10.3185(4)
_cell_length_b                     12.3484(4)
_cell_length_c                     13.2278(5)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1685.45(11)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6098
_cell_measurement_temperature      99.9(8)
_cell_measurement_theta_max        78.9430
_cell_measurement_theta_min        4.8090
_shelx_estimated_absorpt_T_max     0.920
_shelx_estimated_absorpt_T_min     0.826
_exptl_absorpt_coefficient_mu      0.708
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.09312
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     ?
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.314
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               704
_exptl_crystal_preparation         'slow crystallization'
_exptl_crystal_size_max            0.28
_exptl_crystal_size_mid            0.16
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.1165
_diffrn_reflns_av_unetI/netI       0.1015
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         9
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              7447
_diffrn_reflns_point_group_measured_fraction_full  0.965
_diffrn_reflns_point_group_measured_fraction_max  0.965
_diffrn_reflns_theta_full          62.484
_diffrn_reflns_theta_max           62.484
_diffrn_reflns_theta_min           4.899
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        99.9(8)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -6.00  20.00   0.50    0.81    --  -47.47  44.00  75.00   52
  2  ω   -124.00 -67.00   0.50    3.23    -- -106.00-147.00  57.00  114
  3  ω   -163.00-133.00   0.50    3.23    -- -106.00 -77.00 106.00   60
  4  ω   -130.00 -83.00   0.50    3.23    -- -106.00 -77.00 106.00   94
  5  ω   -159.00-129.00   0.50    3.23    -- -106.00-147.00  57.00   60
  6  ω   -117.00 -76.00   0.50    0.81    --  -47.47-147.00  57.00   82
  7  ω   -119.00 -74.00   0.50    0.81    --  -47.47-125.00-120.00   90
  8  ω   -115.00 -73.00   0.50    0.81    --  -47.47-125.00   0.00   84
  9  ω     -9.00  30.00   0.50    0.81    --   47.47 -37.00   0.00   78
 10  ω    -86.00 -34.00   0.50    3.23    -- -106.00  77.00 150.00  104
 11  ω    -67.00 -33.00   0.50    3.23    -- -106.00  61.00-120.00   68
 12  ω     56.00 100.00   0.50    3.23    --  113.25 -77.00-120.00   88
 13  ω     43.00  71.00   0.50    3.23    --  113.25 -61.00 -90.00   56
 14  ω     43.00  71.00   0.50    3.23    --  113.25 -61.00 -60.00   56
 15  ω     59.00 106.00   0.50    3.23    --  113.25 -77.00 -90.00   94
 16  ω     43.00  68.00   0.50    3.23    --  113.25 -61.00-120.00   50
 17  ω    146.00 174.00   0.50    3.23    --  113.25  44.00  75.00   56
 18  ω    -85.00 -59.00   0.50    0.81    --  -47.47-147.00  57.00   52
 19  ω    -23.00  24.00   0.50    0.81    --  -47.47  19.00-150.00   94
 20  ω   -115.00 -89.00   0.50    0.81    --  -47.47-125.00 -30.00   52
 21  ω   -168.00-139.00   0.50    3.23    -- -106.00 -77.00  60.00   58
 22  ω   -115.00 -83.00   0.50    3.23    -- -106.00 -77.00  60.00   64
 23  ω   -128.00-115.50   0.50    3.23    -- -106.00 -45.00  60.00   25
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type   
 'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.1228830000
_diffrn_orient_matrix_UB_12        0.0162774000
_diffrn_orient_matrix_UB_13        0.0642793000
_diffrn_orient_matrix_UB_21        0.0231801000
_diffrn_orient_matrix_UB_22        0.1232592000
_diffrn_orient_matrix_UB_23        -0.0000571000
_diffrn_orient_matrix_UB_31        -0.0814254000
_diffrn_orient_matrix_UB_32        0.0104736000
_diffrn_orient_matrix_UB_33        -0.0971596000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage           0.668
_reflns_Friedel_fraction_full      0.917
_reflns_Friedel_fraction_max       0.917
_reflns_number_gt                  2347
_reflns_number_total               2595
_reflns_odcompleteness_completeness  99.95
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       72.42
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection         'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction          'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.460
_refine_diff_density_min           -0.481
_refine_diff_density_rms           0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 830 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.2(5)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       228
_refine_ls_number_reflns           2595
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1046
_refine_ls_R_factor_gt             0.0850
_refine_ls_restrained_S_all        1.062
_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/[σ²(Fo²)+(0.1804P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.2142
_refine_ls_wR_factor_ref           0.2236
_refine_special_details            ?
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C18(H18), C14(H14), C19(H19), C15(H15), C1(H1A), C9(H9), C4(H4),
 C5(H5), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O -0.7275(4) -0.4782(3) -0.3097(2) 0.0251(10) Uani 1 1 d . . . . .
 O3 O -0.7058(3) -0.2026(3) -0.4284(3) 0.0209(9) Uani 1 1 d . . . . .
 O2 O -0.5421(4) -0.3017(3) -0.3670(3) 0.0264(10) Uani 1 1 d . . . . .
 N1 N -0.7930(4) -0.4732(4) -0.6115(3) 0.0167(10) Uani 1 1 d . . . . .
 H1 H -0.806856 -0.472611 -0.677132 0.020 Uiso 1 1 calc R . . . .
 C10 C -0.7473(5) -0.4781(4) -0.4033(4) 0.0177(12) Uani 1 1 d . . . . .
 C12 C -0.7265(5) -0.3896(4) -0.5697(4) 0.0171(11) Uani 1 1 d . . . . .
 C16 C -0.5837(5) -0.1443(5) -0.7703(4) 0.0211(13) Uani 1 1 d . . . . .
 C18 C -0.5051(5) -0.1884(5) -0.6954(4) 0.0220(12) Uani 1 1 d . . . . .
 H18 H -0.418593 -0.163134 -0.688645 0.026 Uiso 1 1 calc R . . . .
 C20 C -0.6411(5) -0.2943(5) -0.4156(3) 0.0198(12) Uani 1 1 d . . . . .
 C13 C -0.6779(5) -0.3056(4) -0.6390(4) 0.0176(11) Uani 1 1 d . . . . .
 C14 C -0.7554(5) -0.2638(4) -0.7154(4) 0.0179(12) Uani 1 1 d . . . . .
 H14 H -0.841521 -0.289740 -0.723115 0.021 Uiso 1 1 calc R . . . .
 C8 C -0.8392(5) -0.5578(4) -0.5564(4) 0.0187(12) Uani 1 1 d . . . . .
 C19 C -0.5494(5) -0.2680(5) -0.6306(4) 0.0183(12) Uani 1 1 d . . . . .
 H19 H -0.493408 -0.297340 -0.580630 0.022 Uiso 1 1 calc R . . . .
 C15 C -0.7095(5) -0.1848(4) -0.7807(4) 0.0200(12) Uani 1 1 d . . . . .
 H15 H -0.763936 -0.157995 -0.832950 0.024 Uiso 1 1 calc R . . . .
 C7 C -0.9162(5) -0.6419(5) -0.6133(4) 0.0207(12) Uani 1 1 d . . . . .
 H7A H -0.919521 -0.620345 -0.685371 0.025 Uiso 1 1 calc R . . . .
 H7B H -1.006206 -0.640994 -0.587382 0.025 Uiso 1 1 calc R . . . .
 C6 C -0.8663(5) -0.7572(5) -0.6076(4) 0.0181(12) Uani 1 1 d . . . . .
 C1 C -0.7314(6) -0.7778(5) -0.6092(4) 0.0282(14) Uani 1 1 d . . . . .
 H1A H -0.671335 -0.719553 -0.610147 0.034 Uiso 1 1 calc R . . . .
 C9 C -0.8169(5) -0.5617(5) -0.4552(4) 0.0208(12) Uani 1 1 d . . . . .
 H9 H -0.848408 -0.621792 -0.417646 0.025 Uiso 1 1 calc R . . . .
 C11 C -0.7063(5) -0.3882(4) -0.4662(4) 0.0179(12) Uani 1 1 d . . . . .
 C4 C -0.9058(6) -0.9491(5) -0.6081(4) 0.0277(14) Uani 1 1 d . . . . .
 H4 H -0.965584 -1.007550 -0.609218 0.033 Uiso 1 1 calc R . . . .
 C5 C -0.9494(5) -0.8429(5) -0.6065(4) 0.0233(13) Uani 1 1 d . . . . .
 H5 H -1.040060 -0.829560 -0.604456 0.028 Uiso 1 1 calc R . . . .
 C3 C -0.7721(6) -0.9687(5) -0.6081(4) 0.0294(14) Uani 1 1 d . . . . .
 H3 H -0.740210 -1.040831 -0.607174 0.035 Uiso 1 1 calc R . . . .
 C2 C -0.6881(6) -0.8837(6) -0.6094(4) 0.0338(15) Uani 1 1 d . . . . .
 H2 H -0.597532 -0.897510 -0.610375 0.041 Uiso 1 1 calc R . . . .
 C21 C -0.6446(6) -0.1084(5) -0.3859(4) 0.0315(14) Uani 1 1 d . . . . .
 H21A H -0.556682 -0.101498 -0.413224 0.047 Uiso 1 1 calc GR . . . .
 H21B H -0.640382 -0.115766 -0.312247 0.047 Uiso 1 1 calc GR . . . .
 H21C H -0.695007 -0.043834 -0.403416 0.047 Uiso 1 1 calc GR . . . .
 C17 C -0.5353(6) -0.0530(6) -0.8348(4) 0.0323(14) Uani 1 1 d . . . . .
 H17A H -0.577853 0.014462 -0.814309 0.048 Uiso 1 1 calc GR . . . .
 H17B H -0.555038 -0.068119 -0.905835 0.048 Uiso 1 1 calc GR . . . .
 H17C H -0.441352 -0.045723 -0.826241 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 C10 1.255(6) . ?
 O3 C20 1.325(7) . ?
 O3 C21 1.437(7) . ?
 O2 C20 1.211(6) . ?
 N1 C12 1.357(7) . ?
 N1 C8 1.360(7) . ?
 C10 C9 1.433(8) . ?
 C10 C11 1.450(7) . ?
 C12 C13 1.473(7) . ?
 C12 C11 1.386(7) . ?
 C16 C18 1.391(8) . ?
 C16 C15 1.398(8) . ?
 C16 C17 1.499(8) . ?
 C18 C19 1.382(8) . ?
 C20 C11 1.498(8) . ?
 C13 C14 1.388(7) . ?
 C13 C19 1.410(7) . ?
 C14 C15 1.386(7) . ?
 C8 C7 1.509(8) . ?
 C8 C9 1.360(7) . ?
 C7 C6 1.515(9) . ?
 C6 C1 1.415(8) . ?
 C6 C5 1.363(8) . ?
 C1 C2 1.382(10) . ?
 C4 C5 1.386(9) . ?
 C4 C3 1.401(9) . ?
 C3 C2 1.361(9) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C20 O3 C21 114.9(4) . . ?
 C12 N1 C8 122.9(4) . . ?
 O1 C10 C9 123.6(5) . . ?
 O1 C10 C11 121.3(5) . . ?
 C9 C10 C11 115.1(4) . . ?
 N1 C12 C13 117.0(4) . . ?
 N1 C12 C11 119.2(5) . . ?
 C11 C12 C13 123.7(5) . . ?
 C18 C16 C15 118.1(5) . . ?
 C18 C16 C17 120.4(5) . . ?
 C15 C16 C17 121.5(5) . . ?
 C19 C18 C16 121.8(5) . . ?
 O3 C20 C11 112.3(4) . . ?
 O2 C20 O3 123.8(5) . . ?
 O2 C20 C11 123.9(5) . . ?
 C14 C13 C12 121.3(5) . . ?
 C14 C13 C19 118.5(5) . . ?
 C19 C13 C12 120.2(5) . . ?
 C15 C14 C13 121.2(5) . . ?
 N1 C8 C7 116.5(4) . . ?
 C9 C8 N1 119.7(5) . . ?
 C9 C8 C7 123.8(5) . . ?
 C18 C19 C13 119.8(5) . . ?
 C14 C15 C16 120.5(5) . . ?
 C8 C7 C6 116.3(4) . . ?
 C1 C6 C7 120.2(5) . . ?
 C5 C6 C7 121.1(4) . . ?
 C5 C6 C1 118.6(5) . . ?
 C2 C1 C6 119.3(6) . . ?
 C8 C9 C10 122.0(5) . . ?
 C10 C11 C20 117.9(4) . . ?
 C12 C11 C10 120.9(5) . . ?
 C12 C11 C20 121.3(5) . . ?
 C5 C4 C3 118.9(6) . . ?
 C6 C5 C4 122.0(5) . . ?
 C2 C3 C4 119.6(6) . . ?
 C3 C2 C1 121.6(5) . . ?

_olex2_submission_original_sample_id  TZ_247
_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  5.145
_oxdiff_exptl_absorpt_empirical_full_min  0.126
