An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp<sup>3</sup>)-N bond coupling.
Kumari, Santosh; Shakoor, S. M. Abdul; Khullar, Sadhika; Mandal, Sanjay K.; Sakhuja, Rajeev; Organic & biomolecular chemistry 16 (2018) 3220–3228; doi:10.1039/c8ob00586a

data_1549221
_publ_section_title
;
 An unprecedented tandem synthesis of fluorescent coumarin-fused
 pyrimidines via copper-catalyzed cross-dehydrogenative
 C(sp<sup>3</sup>)-N bond coupling.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3220
_journal_page_last               3228
_journal_paper_doi               10.1039/c8ob00586a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.423(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.348(4)
_cell_length_b                   9.871(2)
_cell_length_c                   17.745(4)
_cell_measurement_reflns_used    3528
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.1237
_cell_measurement_theta_min      2.2735
_cell_volume                     3736.0(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26924
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.91
_diffrn_source                   fine-focus
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0423P)^2^+1.0487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                2274
_reflns_number_total             3294
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00586a2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1549221.cif.'
_cod_database_code               1549221
_shelx_res_checksum              25622
_shelx_hkl_checksum              63958