Rhodium-catalyzed regioselective C-h chlorination of 7-azaindoles using 1,2-dichloroethane.
Qian, Guangyin; Hong, Xiaohu; Liu, Bingxin; Mao, Hong; Xu, Bin; Organic letters 16 (2014) 5294–5297; doi:10.1021/ol502447w

data_1517827
_publ_section_title
;
 Rhodium-catalyzed regioselective C-h chlorination of 7-azaindoles using
 1,2-dichloroethane.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5294
_journal_page_last               5297
_journal_paper_doi               10.1021/ol502447w
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C19 H12 Cl2 N2'
_chemical_formula_weight         339.21
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2b 2a'
_symmetry_space_group_name_H-M   'P 21 a b'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.737(3)
_cell_length_b                   10.541(4)
_cell_length_c                   19.242(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1569.3(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9326
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.413
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_coef       0.0058(13)
_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   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0652P)^2^+0.2748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                3086
_reflns_number_total             3554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502447w_si_002.cif
_cod_data_source_block           qgy152b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517827.cif.
;
_cod_original_sg_symbol_H-M      'P 21 ab'
_cod_database_code               1517827