Octahydropyrimido[4,5-g]quinazoline-5,10-diones: Their multicomponent synthesis, self-assembly on graphite and electrochemistry
Van Hoof, Max; Bynens, Lize; Daelemans, Brent; Rodriguez Gonzalez, Miriam Candelaria; Van Meervelt, Luc; De Feyter, Steven; Dehaen, Wim; Chemical Communications  (2022) –; doi:10.1039/D2CC02070J

data_7130234
_publ_section_title
;
 Octahydropyrimido[4,5-g]quinazoline-5,10-diones: Their multicomponent
 synthesis, self-assembly on graphite and electrochemistry
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02070J
_journal_year                    2022
_chemical_formula_moiety         'C34 H44 N4 O2'
_chemical_formula_sum            'C34 H44 N4 O2'
_chemical_formula_weight         540.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-03-30 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                94.653(4)
_cell_angle_beta                 93.966(4)
_cell_angle_gamma                105.856(4)
_cell_formula_units_Z            1
_cell_length_a                   5.8021(2)
_cell_length_b                   9.3374(5)
_cell_length_c                   14.8870(7)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.4540
_cell_measurement_theta_min      3.3770
_cell_volume                     769.77(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_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    -42.00  55.00   1.00   30.00    --  -17.00  38.00  30.00   97
  2  \w    -20.00  25.00   1.00   30.00    --  -17.00 -99.00 150.00   45
  3  \w    -89.00   9.00   1.00   30.00    --  -17.00 -38.00-150.00   98
  4  \w    -20.00  25.00   1.00   30.00    --  -17.00 -99.00 -30.00   45
  5  \w    -38.00  52.00   1.00   30.00    --  -17.00  57.00 150.00   90
  6  \w    -87.00  13.00   1.00   30.00    --  -17.00 -77.00  90.00  100
  7  \w    -86.00   4.00   1.00   30.00    --  -17.00 -57.00   0.00   90
  8  \w    -89.00   9.00   1.00   30.00    --  -17.00 -38.00  90.00   98
  9  \w    -70.00   4.00   1.00   30.00    --  -17.00 118.00-154.00   74
 10  \w     -4.00  72.00   1.00   30.00    --   18.87-118.00 119.00   76
 11  \w     35.00  95.00   1.00   30.00    --   18.87 178.00   0.00   60
 12  \w     -3.00  88.00   1.00   30.00    --   18.87  57.00  30.00   91
 13  \w    -20.00  61.00   1.00   30.00    --   18.87 -99.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164714000
_diffrn_orient_matrix_UB_12      0.0160208000
_diffrn_orient_matrix_UB_13      -0.0453761000
_diffrn_orient_matrix_UB_21      0.0405250000
_diffrn_orient_matrix_UB_22      0.0777664000
_diffrn_orient_matrix_UB_23      0.0144279000
_diffrn_orient_matrix_UB_31      0.1199368000
_diffrn_orient_matrix_UB_32      -0.0003751000
_diffrn_orient_matrix_UB_33      -0.0062377000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15763
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.539
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0794P)^2^+0.1853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1925
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02070j2.cif
_cod_data_source_block           wdh1114
_cod_database_code               7130234
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C34 H44 N4 O2'
_chemical_oxdiff_usercomment     WDH-MVH-CBCH
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.978
_diffrn_oxdiff_ac4_digest_frames
;
01756e854d19d9ed70e8af146addf3dc1d000270ccc
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12A = C11-C12B
 1.5 with sigma of 0.01
3. Rigid bond restraints
 C11, C12A, C12B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C11 \\sim C12A \\sim C12B: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
5. Others
 Sof(H11C)=Sof(H11D)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C11(H11C,H11D)
6.b Me refined with riding coordinates:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              29295
_shelx_hkl_checksum              5555
_olex2_submission_original_sample_id WDH-MVH-CBCH
_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 1.451
_oxdiff_exptl_absorpt_empirical_full_min 0.673