# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_176
_database_code_depnum_ccdc_archive 'CCDC 2236696'
loop_
_audit_author_name
_audit_author_address
'Ekaterina E. Galenko'
;SPbSU
Russia
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 4-(4-fluorophenyl)-2-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate'
_chemical_formula_moiety         'C20 H17 F N2 O4'
_chemical_formula_sum            'C20 H17 F N2 O4'
_chemical_formula_weight         368.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H17 F N2 O4'
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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0037(5)
_cell_length_b                   8.0678(4)
_cell_length_c                   16.6349(10)
_cell_angle_alpha                96.374(5)
_cell_angle_beta                 91.813(6)
_cell_angle_gamma                107.232(6)
_cell_volume                     890.14(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3868
_cell_measurement_temperature    100.00(17)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      5.3240
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       'slove evaporation of metanol solution'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_min         2.679
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  33.00   1.00    1.00    --  -41.44  38.00 -90.00   87
  2  ω   -115.00 -13.00   1.00    1.00    --  -41.44 -57.00 120.00  102
  3  ω     32.00  63.00   1.00    1.00    --   41.44 -99.00  90.00   31
  4  ω    -21.00  73.00   1.00    1.00    --   41.44 -77.00   0.00   94
  5  ω     68.00 128.00   1.00    1.00    --   41.44-178.00  60.00   60
  6  ω     41.00 105.00   1.00    2.00    --  112.00 -95.00 -90.00   64
  7  ω    110.00 169.00   1.00    2.00    --  112.00  77.00-180.00   59
  8  ω     55.00  91.00   1.00    2.00    --  112.00 -45.00-120.00   36
  9  ω    110.00 139.00   1.00    2.00    --  112.00  77.00 150.00   29
 10  ω     82.00 112.00   1.00    2.00    --  112.00-126.00  60.00   30
 11  ω    142.00 176.00   1.00    2.00    --  112.00  77.00 150.00   34
 12  ω     39.00 113.00   1.00    2.00    --  112.00-126.00  30.00   74
 13  ω    138.00 168.00   1.00    2.00    --  112.00 126.00-180.00   30
 14  ω    115.00 173.00   1.00    2.00    --  112.00  77.00-150.00   58
 15  ω     40.00 112.00   1.00    2.00    --  112.00-126.00-180.00   72
 16  ω     55.00  80.00   1.00    2.00    --  112.00 -95.00 150.00   25
 17  ω     74.00 112.00   1.00    2.00    --  112.00-126.00 -90.00   38
 18  ω     85.00 178.00   1.00    2.00    --  112.00  30.00 -60.00   93
 19  ω     41.00 135.00   1.00    2.00    --  112.00 -45.00 120.00   94
 20  ω     79.00 113.00   1.00    2.00    --  112.00-126.00-120.00   34
 21  ω     45.00  70.00   1.00    2.00    --  112.00-126.00   0.00   25
 22  ω     40.00 125.00   1.00    2.00    --  112.00-142.00 158.45   85
 23  ω    -16.00  20.00   1.00    1.00    --    2.00  16.00  78.56   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0387811000
_diffrn_orient_matrix_UB_12      -0.1545585000
_diffrn_orient_matrix_UB_13      -0.0679513000
_diffrn_orient_matrix_UB_21      0.2275333000
_diffrn_orient_matrix_UB_22      0.0336214000
_diffrn_orient_matrix_UB_23      -0.0042528000
_diffrn_orient_matrix_UB_31      -0.0031605000
_diffrn_orient_matrix_UB_32      -0.1248901000
_diffrn_orient_matrix_UB_33      0.0639418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2891
_reflns_number_total             3509
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066
_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     250
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.053
_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/[σ²(Fo²)+(0.0872P)²+0.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C0) = Uanis(C7)
3. Others
 Fixed Sof: H6BC(0.5) H6BD(0.5) H6AA(0.5) H6AB(0.5) C0(0.5) H0A(0.5) H0B(0.5)
 H0C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6BC,H6BD), C6(H6AA,H6AB)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C11(H11), C18(H18), C12(H12), C9(H9), C15(H15), C19(H19),
 C8(H8)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C0(H0A,H0B,H0C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F001 F 1.08377(19) 0.82114(14) 0.99090(7) 0.0334(3) Uani 1 1 d . . . . .
O3 O 0.54101(18) 0.21130(14) 0.81568(7) 0.0204(3) Uani 1 1 d . . . . .
O4 O 0.81839(19) 0.79452(15) 0.29035(8) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.6713(2) 0.00037(16) 0.76738(8) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.5221(2) -0.02052(15) 0.59642(8) 0.0244(3) Uani 1 1 d . . . . .
N2 N 0.7973(2) 0.50341(17) 0.63049(9) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.6407(2) 0.23990(17) 0.54784(9) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.601897 0.187470 0.498216 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6333(2) 0.1351(2) 0.76074(11) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.7511(2) 0.5128(2) 0.48748(10) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.6774(2) 0.2340(2) 0.68953(10) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.7089(2) 0.5296(2) 0.34421(11) 0.0193(4) Uani 1 1 d . . . . .
H16 H 0.663949 0.473151 0.290830 0.023 Uiso 1 1 calc R U . . .
C1 C 0.6086(2) 0.1391(2) 0.61051(11) 0.0176(4) Uani 1 1 d . . . . .
C11 C 0.8167(2) 0.6773(2) 0.79411(11) 0.0178(4) Uani 1 1 d . . . . .
H11 H 0.737286 0.715469 0.757212 0.021 Uiso 1 1 calc R U . . .
C13 C 1.0092(3) 0.7215(2) 0.91902(11) 0.0222(4) Uani 1 1 d . . . . .
C17 C 0.8002(2) 0.7109(2) 0.35717(11) 0.0172(3) Uani 1 1 d . . . . .
C18 C 0.8668(3) 0.7919(2) 0.43526(12) 0.0229(4) Uani 1 1 d . . . . .
H18 H 0.929558 0.914685 0.444700 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8915(3) 0.7794(2) 0.86742(11) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.862484 0.886208 0.881787 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7724(2) 0.4123(2) 0.69548(10) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.8570(2) 0.5188(2) 0.77396(10) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.9770(3) 0.4651(2) 0.82777(11) 0.0203(4) Uani 1 1 d . . . . .
H9 H 1.004876 0.357398 0.814376 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6838(2) 0.4328(2) 0.40827(11) 0.0186(4) Uani 1 1 d . . . . .
H15 H 0.620102 0.310197 0.398729 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7293(2) 0.4167(2) 0.55837(10) 0.0147(3) Uani 1 1 d . . . . .
C19 C 0.8418(3) 0.6938(2) 0.49924(11) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.887244 0.750710 0.552504 0.027 Uiso 1 1 calc R U . . .
C8 C 1.0555(3) 0.5674(2) 0.90034(11) 0.0230(4) Uani 1 1 d . . . . .
H8 H 1.139531 0.532481 0.936594 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4958(3) 0.1271(2) 0.88801(12) 0.0269(4) Uani 1 1 d . . . . .
H6BC H 0.620778 0.132735 0.919238 0.032 Uiso 0.5 1 calc R U P A 2
H6BD H 0.416059 0.002868 0.873844 0.032 Uiso 0.5 1 calc R U P A 2
H6AA H 0.617260 0.107143 0.911820 0.032 Uiso 0.5 1 calc R U P B 1
H6AB H 0.391150 0.012814 0.874972 0.032 Uiso 0.5 1 calc R U P B 1
C20 C 0.8932(3) 0.9826(2) 0.30175(12) 0.0232(4) Uani 1 1 d . . . . .
H20A H 0.889000 1.026572 0.249335 0.035 Uiso 1 1 calc R U . . .
H20B H 1.031655 1.019726 0.325170 0.035 Uiso 1 1 calc R U . . .
H20C H 0.809739 1.029437 0.338506 0.035 Uiso 1 1 calc R U . . .
C0 C 0.382(4) 0.223(3) 0.9349(14) 0.040(2) Uani 0.5 1 d . . P C 2
H0A H 0.458906 0.347112 0.945008 0.061 Uiso 0.5 1 calc R U P C 2
H0B H 0.354303 0.176449 0.986736 0.061 Uiso 0.5 1 calc R U P C 2
H0C H 0.254667 0.209795 0.904548 0.061 Uiso 0.5 1 calc R U P C 2
C7 C 0.420(4) 0.252(3) 0.9493(14) 0.040(2) Uani 0.5 1 d . . P C 1
H7A H 0.520496 0.367798 0.958582 0.061 Uiso 0.5 1 calc R U P C 1
H7B H 0.397110 0.203696 1.000844 0.061 Uiso 0.5 1 calc R U P C 1
H7C H 0.293883 0.263963 0.926800 0.061 Uiso 0.5 1 calc R U P C 1


_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
F001 C13 1.359(2) . ?
O3 C5 1.334(2) . ?
O3 C6 1.445(2) . ?
O4 C17 1.354(2) . ?
O4 C20 1.4390(19) . ?
O2 C5 1.209(2) . ?
O1 C1 1.242(2) . ?
N2 C3 1.361(2) . ?
N2 C4 1.318(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.376(2) . ?
N1 C4 1.365(2) . ?
C5 C2 1.491(2) . ?
C14 C15 1.402(2) . ?
C14 C4 1.469(2) . ?
C14 C19 1.398(2) . ?
C2 C1 1.437(2) . ?
C2 C3 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(2) . ?
C16 C15 1.375(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C11 C10 1.397(2) . ?
C13 C12 1.381(3) . ?
C13 C8 1.381(3) . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(3) . ?
C12 H12 0.9500 . ?
C3 C10 1.481(2) . ?
C10 C9 1.396(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.382(3) . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C6 C0 1.46(3) . ?
C6 C7 1.57(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C0 H0A 0.9800 . ?
C0 H0B 0.9800 . ?
C0 H0C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
C5 O3 C6 115.68(13) . . ?
C17 O4 C20 117.80(14) . . ?
C4 N2 C3 118.06(14) . . ?
C1 N1 H1 118.2 . . ?
C4 N1 H1 118.2 . . ?
C4 N1 C1 123.64(14) . . ?
O3 C5 C2 111.50(13) . . ?
O2 C5 O3 123.87(16) . . ?
O2 C5 C2 124.60(15) . . ?
C15 C14 C4 123.50(14) . . ?
C19 C14 C15 117.87(16) . . ?
C19 C14 C4 118.63(15) . . ?
C1 C2 C5 117.57(14) . . ?
C3 C2 C5 123.90(15) . . ?
C3 C2 C1 118.46(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.40(16) . . ?
O1 C1 N1 119.97(15) . . ?
O1 C1 C2 125.19(16) . . ?
N1 C1 C2 114.82(14) . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.61(16) . . ?
C10 C11 H11 119.7 . . ?
F001 C13 C12 118.57(15) . . ?
F001 C13 C8 118.69(16) . . ?
C12 C13 C8 122.73(17) . . ?
O4 C17 C16 116.02(15) . . ?
O4 C17 C18 124.62(15) . . ?
C18 C17 C16 119.35(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.92(16) . . ?
C19 C18 H18 120.0 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.20(15) . . ?
C13 C12 H12 120.9 . . ?
N2 C3 C2 123.27(15) . . ?
N2 C3 C10 114.63(13) . . ?
C2 C3 C10 122.10(15) . . ?
C11 C10 C3 119.05(15) . . ?
C9 C10 C11 119.41(16) . . ?
C9 C10 C3 121.54(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.48(15) . . ?
C8 C9 H9 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.89(15) . . ?
C16 C15 H15 119.6 . . ?
N2 C4 N1 121.67(15) . . ?
N2 C4 C14 119.05(14) . . ?
N1 C4 C14 119.28(15) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.55(17) . . ?
C18 C19 H19 119.2 . . ?
C13 C8 C9 118.55(16) . . ?
C13 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
O3 C6 H6BC 110.6 . . ?
O3 C6 H6BD 110.6 . . ?
O3 C6 H6AA 110.3 . . ?
O3 C6 H6AB 110.3 . . ?
O3 C6 C0 105.8(12) . . ?
O3 C6 C7 107.1(11) . . ?
H6BC C6 H6BD 108.7 . . ?
H6AA C6 H6AB 108.5 . . ?
C0 C6 H6BC 110.6 . . ?
C0 C6 H6BD 110.6 . . ?
C7 C6 H6AA 110.3 . . ?
C7 C6 H6AB 110.3 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C0 H0A 109.5 . . ?
C6 C0 H0B 109.5 . . ?
C6 C0 H0C 109.5 . . ?
H0A C0 H0B 109.5 . . ?
H0A C0 H0C 109.5 . . ?
H0B C0 H0C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C13 C12 C11 179.77(15) . . . . ?
F001 C13 C8 C9 179.01(15) . . . . ?
O3 C5 C2 C1 -126.50(15) . . . . ?
O3 C5 C2 C3 50.6(2) . . . . ?
O4 C17 C18 C19 -179.59(16) . . . . ?
O2 C5 C2 C1 51.8(2) . . . . ?
O2 C5 C2 C3 -131.17(19) . . . . ?
N2 C3 C10 C11 47.4(2) . . . . ?
N2 C3 C10 C9 -132.12(16) . . . . ?
C5 O3 C6 C0 -175.2(7) . . . . ?
C5 O3 C6 C7 171.4(8) . . . . ?
C5 C2 C1 O1 -3.0(2) . . . . ?
C5 C2 C1 N1 175.39(13) . . . . ?
C5 C2 C3 N2 -174.48(14) . . . . ?
C5 C2 C3 C10 6.0(2) . . . . ?
C2 C3 C10 C11 -133.13(17) . . . . ?
C2 C3 C10 C9 47.4(2) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C1 N1 C4 N2 2.3(2) . . . . ?
C1 N1 C4 C14 -178.23(13) . . . . ?
C1 C2 C3 N2 2.6(2) . . . . ?
C1 C2 C3 C10 -176.92(13) . . . . ?
C11 C10 C9 C8 0.0(3) . . . . ?
C17 C16 C15 C14 -0.8(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C12 C11 C10 C3 179.27(15) . . . . ?
C12 C11 C10 C9 -1.2(2) . . . . ?
C12 C13 C8 C9 -1.5(3) . . . . ?
C3 N2 C4 N1 -1.7(2) . . . . ?
C3 N2 C4 C14 178.89(13) . . . . ?
C3 C2 C1 O1 179.73(16) . . . . ?
C3 C2 C1 N1 -1.8(2) . . . . ?
C3 C10 C9 C8 179.47(16) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C10 C9 C8 C13 1.3(3) . . . . ?
C15 C14 C4 N2 -179.99(14) . . . . ?
C15 C14 C4 N1 0.5(2) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C15 C16 C17 O4 179.88(14) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C4 N2 C3 C2 -0.8(2) . . . . ?
C4 N2 C3 C10 178.73(13) . . . . ?
C4 N1 C1 O1 178.06(14) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
C4 C14 C15 C16 -179.84(14) . . . . ?
C4 C14 C19 C18 -179.97(15) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C19 C14 C4 N2 -0.7(2) . . . . ?
C19 C14 C4 N1 179.88(14) . . . . ?
C8 C13 C12 C11 0.2(3) . . . . ?
C6 O3 C5 O2 3.1(2) . . . . ?
C6 O3 C5 C2 -178.65(14) . . . . ?
C20 O4 C17 C16 174.00(14) . . . . ?
C20 O4 C17 C18 -6.7(2) . . . . ?

_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 3.149
_oxdiff_exptl_absorpt_empirical_full_min 0.394
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22-172
_database_code_depnum_ccdc_archive 'CCDC 2236697'
loop_
_audit_author_name
_audit_author_address
'Ekaterina E. Galenko'
;SPbSU
Russia
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'ethyl 2-phenyl-4-(phenyl(pyridin-2-yl)amino)-6-(p-tolyl)pyrimidine-5-carboxylate'
_chemical_formula_moiety         'C31 H26 N4 O2'
_chemical_formula_sum            'C31 H26 N4 O2'
_chemical_formula_weight         486.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C31H26 N4 O2'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.0365(3)
_cell_length_b                   7.74810(10)
_cell_length_c                   20.9647(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.459(2)
_cell_angle_gamma                90
_cell_volume                     2484.91(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2220
_cell_measurement_theta_min      2.8820
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_preparation       'slow evaporation of MeOH solution'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16192
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.485
_diffrn_reflns_theta_min         2.889
_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 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   0.00   0.50    4.00    --  -47.38  23.00-178.00   50
  2  ω   -121.00 -35.00   0.50    4.00    --  -47.38 -23.00  17.00  172
  3  ω     49.00 118.00   0.50    4.00    --   47.38  23.00-178.00  138
  4  ω     -3.00  23.00   0.50    4.00    --   47.38 -23.00  17.00   52
  5  ω   -158.00 -93.00   0.50   22.00    -- -105.93 -23.00  17.00  130
  6  ω     93.00 142.00   0.50   22.00    --  105.93  23.00-178.00   98
  7  ω    -19.00  26.00   0.50    4.00    --  -47.38  19.00 -30.00   90
  8  ω    -22.00  41.00   0.50    4.00    --   47.38 -37.00-120.00  126
  9  ω   -176.00-119.00   0.50   22.00    -- -105.93 -15.00  90.00  114
 10  ω    -71.00 -46.00   0.50   22.00    -- -105.93  61.00-180.00   50
 11  ω   -110.00 -62.00   0.50   22.00    -- -105.93 125.00-120.00   96
 12  ω   -173.00-119.00   0.50   22.00    -- -105.93 -30.00 -30.00  108
 13  ω     40.00  70.00   0.50   22.00    --  105.93 -61.00-120.00   60
 14  ω     34.00  70.00   0.50   22.00    --  105.93 -61.00 -60.00   72
 15  ω     35.00  66.00   0.50   22.00    --  105.93 -61.00  60.00   62
 16  ω     40.00  81.00   0.50   22.00    --  105.93 -77.00-150.00   82
 17  ω     41.00  66.00   0.50   22.00    --  105.93 -61.00  90.00   50
 18  ω     57.00 104.00   0.50   22.00    --  105.93-125.00   0.00   94
 19  ω     33.00  63.00   0.50   22.00    --  105.93 -61.00 -30.00   60
 20  ω     36.00 101.00   0.50   22.00    --  105.93 -77.00  30.00  130
 21  ω     35.00  60.00   0.50   22.00    --  105.93 -61.00-180.00   50
 22  ω     33.00  69.00   0.50   22.00    --  105.93 -61.00 -90.00   72
 23  ω     41.00  71.00   0.50   22.00    --  105.93 -61.00-150.00   60
;
_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      0.0981269000
_diffrn_orient_matrix_UB_12      -0.0101084000
_diffrn_orient_matrix_UB_13      0.0386828000
_diffrn_orient_matrix_UB_21      -0.0196111000
_diffrn_orient_matrix_UB_22      0.0608512000
_diffrn_orient_matrix_UB_23      0.0640074000
_diffrn_orient_matrix_UB_31      -0.0113979000
_diffrn_orient_matrix_UB_32      -0.1889281000
_diffrn_orient_matrix_UB_33      0.0185752000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4290
_reflns_number_total             4865
_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 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.041
_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/[σ²(Fo²)+(0.0476P)²+1.8270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C25)
Uanis(C24) = Uanis(C22)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C15(H15), C25(H25), C19(H19), C16(H16), C11(H11), C22(H22),
 C17(H17), C27(H27), C23(H23), C18(H18), C24(H24), C10(H10), C6(H6), C28(H28),
 C7(H7), C29(H29), C30(H30)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O2 O 0.57859(7) 0.33443(15) 0.11546(5) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.65208(8) 0.50924(16) 0.06502(6) 0.0239(3) Uani 1 1 d . . . . .
N3 N 0.82780(9) 0.43207(17) 0.17528(7) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.68024(9) 0.64621(17) 0.28646(7) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.81693(9) 0.56564(17) 0.27177(7) 0.0179(3) Uani 1 1 d . . . . .
C21 C 0.90075(11) 0.6975(2) 0.17281(8) 0.0191(2) Uani 1 1 d . . . . .
H21 H 0.847878 0.755213 0.171135 0.023 Uiso 1 1 calc R U . . .
C20 C 0.90482(10) 0.5222(2) 0.17479(7) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.76720(10) 0.6317(2) 0.30724(8) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.68399(10) 0.5154(2) 0.18405(8) 0.0171(3) Uani 1 1 d . . . . .
N4 N 0.75941(11) 0.1610(2) 0.16979(9) 0.0324(4) Uani 1 1 d . . . . .
C26 C 0.80351(10) 0.2724(2) 0.14185(8) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.63823(11) 0.5913(2) 0.22445(8) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.81313(11) 0.6930(2) 0.37588(8) 0.0183(3) Uani 1 1 d . . . . .
C31 C 0.63766(10) 0.4546(2) 0.11463(8) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.77490(10) 0.50570(19) 0.21095(8) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.54257(10) 0.6209(2) 0.20199(8) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.76737(11) 0.7883(2) 0.41123(8) 0.0206(3) Uani 1 1 d . . . . .
H15 H 0.706586 0.808980 0.391991 0.025 Uiso 1 1 calc R U . . .
C25 C 0.98153(10) 0.4349(2) 0.17650(8) 0.0191(2) Uani 1 1 d . . . . .
H25 H 0.983674 0.312363 0.177732 0.023 Uiso 1 1 calc R U . . .
C19 C 0.90184(11) 0.6597(2) 0.40571(8) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.933140 0.592197 0.382740 0.027 Uiso 1 1 calc R U . . .
C8 C 0.36160(11) 0.6830(2) 0.16426(9) 0.0246(4) Uani 1 1 d . . . . .
C16 C 0.81059(12) 0.8528(2) 0.47442(8) 0.0246(4) Uani 1 1 d . . . . .
H16 H 0.779284 0.917525 0.498204 0.029 Uiso 1 1 calc R U . . .
C11 C 0.49866(11) 0.6800(2) 0.13802(9) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.530029 0.699303 0.106769 0.029 Uiso 1 1 calc R U . . .
C22 C 0.97367(11) 0.7898(2) 0.17326(9) 0.0258(3) Uani 1 1 d . . . . .
H22 H 0.970907 0.912262 0.172328 0.031 Uiso 1 1 calc R U . . .
C17 C 0.89912(12) 0.8228(2) 0.50274(8) 0.0256(4) Uani 1 1 d . . . . .
H17 H 0.928819 0.869380 0.545444 0.031 Uiso 1 1 calc R U . . .
C27 C 0.82184(12) 0.2346(2) 0.08242(8) 0.0239(4) Uani 1 1 d . . . . .
H27 H 0.852576 0.314650 0.063509 0.029 Uiso 1 1 calc R U . . .
C23 C 1.05137(11) 0.7091(2) 0.17506(9) 0.0266(4) Uani 1 1 d . . . . .
H23 H 1.101431 0.775070 0.175365 0.032 Uiso 1 1 calc R U . . .
C18 C 0.94454(12) 0.7246(2) 0.46867(9) 0.0259(4) Uani 1 1 d . . . . .
H18 H 1.004999 0.701887 0.488587 0.031 Uiso 1 1 calc R U . . .
C24 C 1.05474(12) 0.5306(2) 0.17639(9) 0.0258(3) Uani 1 1 d . . . . .
H24 H 1.107417 0.473272 0.177224 0.031 Uiso 1 1 calc R U . . .
C10 C 0.40933(11) 0.7109(2) 0.11959(9) 0.0256(4) Uani 1 1 d . . . . .
H10 H 0.380294 0.751705 0.075821 0.031 Uiso 1 1 calc R U . . .
C6 C 0.49521(12) 0.5936(3) 0.24699(9) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.524145 0.553464 0.290886 0.033 Uiso 1 1 calc R U . . .
C28 C 0.79430(13) 0.0777(2) 0.05150(9) 0.0304(4) Uani 1 1 d . . . . .
H28 H 0.807317 0.048407 0.011523 0.036 Uiso 1 1 calc R U . . .
C12 C 0.52510(12) 0.2732(2) 0.05052(9) 0.0282(4) Uani 1 1 d . . . . .
H12A H 0.562554 0.227584 0.024496 0.034 Uiso 1 1 calc R U . . .
H12B H 0.489208 0.368639 0.024940 0.034 Uiso 1 1 calc R U . . .
C7 C 0.40613(12) 0.6248(3) 0.22792(10) 0.0311(4) Uani 1 1 d . . . . .
H7 H 0.374756 0.605781 0.259195 0.037 Uiso 1 1 calc R U . . .
C29 C 0.74795(13) -0.0362(3) 0.07868(11) 0.0353(5) Uani 1 1 d . . . . .
H29 H 0.727900 -0.143158 0.057451 0.042 Uiso 1 1 calc R U . . .
C9 C 0.26508(12) 0.7187(3) 0.14446(11) 0.0349(4) Uani 1 1 d . . . . .
H9A H 0.252046 0.822457 0.116459 0.052 Uiso 1 1 calc R U . . .
H9B H 0.247091 0.736843 0.184695 0.052 Uiso 1 1 calc R U . . .
H9C H 0.233168 0.620237 0.119318 0.052 Uiso 1 1 calc R U . . .
C13 C 0.46776(14) 0.1338(3) 0.06320(10) 0.0369(5) Uani 1 1 d . . . . .
H13A H 0.429782 0.090235 0.020461 0.055 Uiso 1 1 calc R U . . .
H13B H 0.431775 0.180263 0.089604 0.055 Uiso 1 1 calc R U . . .
H13C H 0.504075 0.039461 0.087870 0.055 Uiso 1 1 calc R U . . .
C30 C 0.73152(14) 0.0093(3) 0.13741(12) 0.0380(5) Uani 1 1 d . . . . .
H30 H 0.699382 -0.068378 0.156084 0.046 Uiso 1 1 calc R U . . .


_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
O2 C31 1.332(2) . ?
O2 C12 1.4538(19) . ?
O1 C31 1.208(2) . ?
N3 C20 1.422(2) . ?
N3 C26 1.417(2) . ?
N3 C2 1.409(2) . ?
N1 C1 1.335(2) . ?
N1 C4 1.341(2) . ?
N2 C1 1.344(2) . ?
N2 C2 1.334(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.359(2) . ?
C21 C22 1.368(2) . ?
C20 C25 1.395(2) . ?
C1 C14 1.484(2) . ?
C3 C4 1.405(2) . ?
C3 C31 1.498(2) . ?
C3 C2 1.399(2) . ?
N4 C26 1.356(2) . ?
N4 C30 1.364(3) . ?
C26 C27 1.395(2) . ?
C4 C5 1.481(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.396(2) . ?
C5 C11 1.392(2) . ?
C5 C6 1.393(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.386(2) . ?
C8 C10 1.393(3) . ?
C8 C7 1.387(3) . ?
C8 C9 1.503(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.388(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(3) . ?
C18 H18 0.9500 . ?
C24 H24 0.9500 . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.382(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.493(3) . ?
C7 H7 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.380(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C30 H30 0.9500 . ?

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
C31 O2 C12 115.96(13) . . ?
C26 N3 C20 122.38(13) . . ?
C2 N3 C20 117.88(13) . . ?
C2 N3 C26 119.73(13) . . ?
C1 N1 C4 117.45(13) . . ?
C2 N2 C1 116.60(14) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.26(16) . . ?
C22 C21 H21 120.4 . . ?
C21 C20 N3 117.20(14) . . ?
C21 C20 C25 121.28(15) . . ?
C25 C20 N3 121.52(14) . . ?
N1 C1 N2 125.92(14) . . ?
N1 C1 C14 117.07(14) . . ?
N2 C1 C14 117.00(14) . . ?
C4 C3 C31 121.40(14) . . ?
C2 C3 C4 116.70(14) . . ?
C2 C3 C31 121.86(14) . . ?
C26 N4 C30 118.00(17) . . ?
N4 C26 N3 116.35(14) . . ?
N4 C26 C27 121.95(16) . . ?
C27 C26 N3 121.68(15) . . ?
N1 C4 C3 121.05(15) . . ?
N1 C4 C5 115.46(14) . . ?
C3 C4 C5 123.47(14) . . ?
C15 C14 C1 119.72(15) . . ?
C19 C14 C1 121.19(14) . . ?
C19 C14 C15 119.09(15) . . ?
O2 C31 C3 110.77(13) . . ?
O1 C31 O2 125.24(15) . . ?
O1 C31 C3 123.98(15) . . ?
N2 C2 N3 115.87(14) . . ?
N2 C2 C3 122.22(14) . . ?
C3 C2 N3 121.92(14) . . ?
C11 C5 C4 122.25(14) . . ?
C11 C5 C6 118.78(15) . . ?
C6 C5 C4 118.95(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.21(16) . . ?
C16 C15 H15 119.9 . . ?
C20 C25 H25 120.7 . . ?
C24 C25 C20 118.68(16) . . ?
C24 C25 H25 120.7 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.37(16) . . ?
C18 C19 H19 119.8 . . ?
C10 C8 C9 120.93(17) . . ?
C7 C8 C10 117.99(16) . . ?
C7 C8 C9 121.07(17) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.15(16) . . ?
C17 C16 H16 119.9 . . ?
C5 C11 H11 119.8 . . ?
C10 C11 C5 120.43(16) . . ?
C10 C11 H11 119.8 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.65(17) . . ?
C23 C22 H22 119.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.96(16) . . ?
C18 C17 H17 120.0 . . ?
C26 C27 H27 120.7 . . ?
C28 C27 C26 118.65(17) . . ?
C28 C27 H27 120.7 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.76(17) . . ?
C24 C23 H23 120.6 . . ?
C19 C18 C17 120.17(17) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.37(16) . . ?
C23 C24 H24 119.8 . . ?
C8 C10 H10 119.5 . . ?
C11 C10 C8 121.04(16) . . ?
C11 C10 H10 119.5 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.19(17) . . ?
C7 C6 H6 119.9 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.17(17) . . ?
C29 C28 H28 119.9 . . ?
O2 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
O2 C12 C13 106.92(15) . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.57(17) . . ?
C6 C7 H7 119.2 . . ?
C28 C29 H29 120.8 . . ?
C30 C29 C28 118.36(18) . . ?
C30 C29 H29 120.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C30 C29 122.85(19) . . ?
N4 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C20 C25 C24 -179.55(14) . . . . ?
N3 C26 C27 C28 -178.41(15) . . . . ?
N1 C1 C14 C15 -10.8(2) . . . . ?
N1 C1 C14 C19 170.20(15) . . . . ?
N1 C4 C5 C11 137.36(16) . . . . ?
N1 C4 C5 C6 -40.7(2) . . . . ?
N2 C1 C14 C15 169.56(14) . . . . ?
N2 C1 C14 C19 -9.4(2) . . . . ?
C21 C20 C25 C24 0.2(2) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C20 N3 C26 N4 148.53(15) . . . . ?
C20 N3 C26 C27 -33.3(2) . . . . ?
C20 N3 C2 N2 -45.35(19) . . . . ?
C20 N3 C2 C3 134.53(15) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C20 C25 C24 C23 0.4(3) . . . . ?
C1 N1 C4 C3 2.4(2) . . . . ?
C1 N1 C4 C5 -176.01(14) . . . . ?
C1 N2 C2 N3 -178.10(13) . . . . ?
C1 N2 C2 C3 2.0(2) . . . . ?
C1 C14 C15 C16 -177.21(15) . . . . ?
C1 C14 C19 C18 177.10(15) . . . . ?
C3 C4 C5 C11 -41.0(2) . . . . ?
C3 C4 C5 C6 140.97(17) . . . . ?
N4 C26 C27 C28 -0.3(3) . . . . ?
C26 N3 C20 C21 144.07(15) . . . . ?
C26 N3 C20 C25 -36.2(2) . . . . ?
C26 N3 C2 N2 134.23(15) . . . . ?
C26 N3 C2 C3 -45.9(2) . . . . ?
C26 N4 C30 C29 1.4(3) . . . . ?
C26 C27 C28 C29 1.4(3) . . . . ?
C4 N1 C1 N2 -0.5(2) . . . . ?
C4 N1 C1 C14 179.93(14) . . . . ?
C4 C3 C31 O2 -59.71(19) . . . . ?
C4 C3 C31 O1 119.70(18) . . . . ?
C4 C3 C2 N3 179.84(14) . . . . ?
C4 C3 C2 N2 -0.3(2) . . . . ?
C4 C5 C11 C10 -178.11(16) . . . . ?
C4 C5 C6 C7 178.25(17) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C14 C19 C18 C17 0.3(3) . . . . ?
C31 O2 C12 C13 176.84(15) . . . . ?
C31 C3 C4 N1 -179.68(14) . . . . ?
C31 C3 C4 C5 -1.5(2) . . . . ?
C31 C3 C2 N3 -2.5(2) . . . . ?
C31 C3 C2 N2 177.39(14) . . . . ?
C2 N3 C20 C21 -36.4(2) . . . . ?
C2 N3 C20 C25 143.41(15) . . . . ?
C2 N3 C26 N4 -31.0(2) . . . . ?
C2 N3 C26 C27 147.16(16) . . . . ?
C2 N2 C1 N1 -1.7(2) . . . . ?
C2 N2 C1 C14 177.89(13) . . . . ?
C2 C3 C4 N1 -2.0(2) . . . . ?
C2 C3 C4 C5 176.23(14) . . . . ?
C2 C3 C31 O2 122.73(16) . . . . ?
C2 C3 C31 O1 -57.9(2) . . . . ?
C5 C11 C10 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C15 C14 C19 C18 -1.9(2) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C19 C14 C15 C16 1.8(2) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C11 C5 C6 C7 0.1(3) . . . . ?
C22 C21 C20 N3 179.04(14) . . . . ?
C22 C21 C20 C25 -0.7(2) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C27 C28 C29 C30 -1.1(3) . . . . ?
C10 C8 C7 C6 -0.4(3) . . . . ?
C6 C5 C11 C10 0.0(3) . . . . ?
C28 C29 C30 N4 -0.4(3) . . . . ?
C12 O2 C31 O1 -3.4(2) . . . . ?
C12 O2 C31 C3 176.05(14) . . . . ?
C7 C8 C10 C11 0.5(3) . . . . ?
C9 C8 C10 C11 179.21(17) . . . . ?
C9 C8 C7 C6 -179.14(18) . . . . ?
C30 N4 C26 N3 177.10(17) . . . . ?
C30 N4 C26 C27 -1.1(3) . . . . ?

_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 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.361
