Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds and Hydrazines with Diaziridinone under Mild Conditions.
Zhu, Yingguang; Shi, Yian; Organic letters 15 (2013) 1942–1945; doi:10.1021/ol4005917

data_1511927
_publ_section_title
;
 Facile Cu(I)-Catalyzed Oxidative Coupling of Anilines to Azo Compounds
 and Hydrazines with Diaziridinone under Mild Conditions.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1942
_journal_page_last               1945
_journal_paper_doi               10.1021/ol4005917
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C24.50 H17 Br4 Cl N2'
_chemical_formula_sum            'C24.5 H17 Br4 Cl N2'
_chemical_formula_weight         694.49
_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                 102.053(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2092(10)
_cell_length_b                   44.486(4)
_cell_length_c                   10.0656(8)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.08
_cell_measurement_theta_min      2.26
_cell_volume                     4908.6(7)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.1040
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            63640
_diffrn_reflns_theta_full        24.80
_diffrn_reflns_theta_max         24.80
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    6.684
_exptl_absorpt_correction_T_max  0.6447
_exptl_absorpt_correction_T_min  0.3468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.319
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0179P)^2^+18.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                5509
_reflns_number_total             8142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4005917_si_001.cif
_cod_data_source_block           shi04_p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C24.50 H17 Br4 Cl N2'
_cod_database_code               1511927