Copper-catalyzed synthesis of quinoxalines with o-phenylenediamine and terminal alkyne in the presence of bases.
Wang, Wen; Shen, Yongwen; Meng, Xu; Zhao, Mingming; Chen, Yongxin; Chen, Baohua; Organic letters 13 (2011) 4514–4517; doi:10.1021/ol201664x

data_1502366
_publ_section_title
;
 Copper-catalyzed synthesis of quinoxalines with o-phenylenediamine and
 terminal alkyne in the presence of bases.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4514
_journal_page_last               4517
_journal_paper_doi               10.1021/ol201664x
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C24 H18 N2'
_chemical_formula_weight         334.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.098(12)
_cell_angle_beta                 63.868(13)
_cell_angle_gamma                77.085(13)
_cell_formula_units_Z            2
_cell_length_a                   10.102(10)
_cell_length_b                   10.247(10)
_cell_length_c                   10.715(10)
_cell_measurement_reflns_used    729
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.24
_cell_volume                     915.5(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1127
_diffrn_reflns_av_sigmaI/netI    0.2056
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6133
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.147
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2653
_refine_ls_R_factor_gt           0.1396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                1138
_reflns_number_total             3123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201664x_si_001.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        915.4(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502366