Base-promoted cross-dehydrogenative coupling of quinoline N-oxides with 1,3-azoles.
Chen, Xiaopei; Cui, Xiuling; Yang, Fangfang; Wu, Yangjie; Organic letters 17 (2015) 1445–1448; doi:10.1021/acs.orglett.5b00330

data_1554822
_publ_section_title
;
 Base-promoted cross-dehydrogenative coupling of quinoline N-oxides with
 1,3-azoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1445
_journal_page_last               1448
_journal_paper_doi               10.1021/acs.orglett.5b00330
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H10 N2 O'
_chemical_formula_sum            'C16 H10 N2 O'
_chemical_formula_weight         246.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.274(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4176(3)
_cell_length_b                   20.0965(10)
_cell_length_c                   9.3350(5)
_cell_measurement_reflns_used    1298
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.3770
_cell_measurement_theta_min      3.7890
_cell_volume                     1191.42(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
  1 omega  -40.00   -5.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000 -150.0000 35

  2 omega   -1.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   37.0000  120.0000 86

  3 omega  -50.00   46.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000  -60.0000 96

  4 omega   -6.00   19.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   37.0000    0.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0513716000
_diffrn_orient_matrix_UB_12      -0.0311119000
_diffrn_orient_matrix_UB_13      0.0032610000
_diffrn_orient_matrix_UB_21      0.0358750000
_diffrn_orient_matrix_UB_22      -0.0017902000
_diffrn_orient_matrix_UB_23      0.0753649000
_diffrn_orient_matrix_UB_31      -0.0924874000
_diffrn_orient_matrix_UB_32      0.0165651000
_diffrn_orient_matrix_UB_33      0.0141799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5751
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.0760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1863
_reflns_number_total             2736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00330_si_002.cif
_cod_data_source_block           201410199
_cod_original_cell_volume        1191.41(10)
_cod_database_code               1554822
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'