Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of Quinoline-Based Dihydropyrimido[1,2-<i>a</i>]quinolin-3-ones on Water.
Belyaeva, Kseniya V.; Nikitina, Lina P.; Mal'kina, Anastasiya G.; Afonin, Andrei V.; Vashchenko, Alexander V.; Trofimov, Boris A.; The Journal of organic chemistry 84 (2019) 9726–9733; doi:10.1021/acs.joc.9b01482

data_4034383
_publ_section_title
;
 Cyanoacetylenes as Triggers and Partners in KOH-Assisted Assemblies of
 Quinoline-Based Dihydropyrimido[1,2-<i>a</i>]quinolin-3-ones on Water.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9726
_journal_page_last               9733
_journal_paper_doi               10.1021/acs.joc.9b01482
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H14 N2 O'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_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
_audit_creation_date             2016-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2019-03-11 # Formatted by publCIF

;
_cell_angle_alpha                108.674(5)
_cell_angle_beta                 101.616(5)
_cell_angle_gamma                98.853(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9945(13)
_cell_length_b                   8.1909(14)
_cell_length_c                   11.3613(19)
_cell_measurement_reflns_used    765
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.6
_cell_measurement_theta_min      2.5
_cell_volume                     671.0(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 0.79
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  No
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22052
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.163
_diffrn_reflns_theta_min         2.676
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1753 before and 0.1073 after correction.
The Ratio of minimum to maximum transmission is 0.6732.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       'yellow, needle, clear'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.607
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.029(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0660
_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^)+(0.1076P)^2^+0.0136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             3902
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01482_si_002.cif
_cod_data_source_block           a
_cod_database_code               4034383
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C15(H15), C17(H17), C18(H18)
;
_shelx_res_checksum              27283
_shelx_hkl_checksum              23730
_olex2_submission_special_instructions 'No special instructions were received'