Bu4NI Catalyzed C-N Bond Formation via Cross-Dehydrogenative Coupling of Aryl Ethers (Csp3-H) and Tetrazoles (N-H).
Rajamanickam, Suresh; Majji, Ganesh; Santra, Sourav Kumar; Patel, Bhisma K.; Organic letters 17 (2015) 5586–5589; doi:10.1021/acs.orglett.5b02749

data_1540621
_publ_section_title
;
 Bu4NI Catalyzed C-N Bond Formation via Cross-Dehydrogenative Coupling of
 Aryl Ethers (Csp3-H) and Tetrazoles (N-H).
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5586
_journal_page_last               5589
_journal_paper_doi               10.1021/acs.orglett.5b02749
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C14 H11 Br N4 O'
_chemical_formula_sum            'C14 H11 Br N4 O'
_chemical_formula_weight         331.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.152(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7522(8)
_cell_length_b                   13.9738(8)
_cell_length_c                   6.7673(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1373.20(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14734
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_T_max  0.513
_exptl_absorpt_correction_T_min  0.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'face indexing'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0274(19)
_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   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.3979P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1560
_reflns_number_total             2415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02749_si_002.cif
_cod_data_source_block           rsh-66
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1540621