Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions.
Panday, Anoop Kumar; Mishra, Richa; Jana, Asim; Parvin, Tasneem; Choudhury, Lokman H.; The Journal of organic chemistry 83 (2018) 3624–3632; doi:10.1021/acs.joc.7b03272

data_4035502
_publ_section_title
;
 Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed
 Domino Reactions.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3624
_journal_page_last               3632
_journal_paper_doi               10.1021/acs.joc.7b03272
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C13 H11 N3 O2'
_chemical_formula_sum            'C13 H11 N3 O2'
_chemical_formula_weight         241.25
_chemical_melting_point          203.5(5)
_chemical_name_common
1,3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)-dione
_chemical_name_systematic
1,3-dimethylpyrimido[4,5-b]quinoline-2,4(1H,3H)-dione
_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_method           SHELXL-2014/7
_audit_update_record
;
2017-10-05 deposited with the CCDC.
2017-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                81.726(6)
_cell_angle_beta                 82.755(6)
_cell_angle_gamma                79.692(6)
_cell_formula_units_Z            4
_cell_length_a                   8.4637(18)
_cell_length_b                   10.759(2)
_cell_length_c                   12.736(2)
_cell_measurement_reflns_used    7133
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      2.80
_cell_volume                     1123.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker apex3 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.459
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         24457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0546P)^2^+0.9878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13591
_reflns_number_total             24457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03272_si_002.cif
_cod_data_source_block           anoop_pras_3_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '203-204' was changed to
'203.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035502
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              46403
_shelx_hkl_checksum              55723