Regioselective Synthesis of N<sup>2</sup>-Alkylated-1,2,3 Triazoles and N<sup>1</sup>-Alkylated Benzotriazoles: Cu<sub>2</sub>S as a Recyclable Nanocatalyst for Oxidative Amination of N, N-Dimethylbenzylamines.
Gupta, Sonu; Chandna, Nisha; Singh, Ajai K.; Jain, Nidhi; The Journal of organic chemistry 83 (2018) 3226–3235; doi:10.1021/acs.joc.8b00107

data_4033532
_publ_section_title
;
 Regioselective Synthesis of N<sup>2</sup>-Alkylated-1,2,3 Triazoles and
 N<sup>1</sup>-Alkylated Benzotriazoles: Cu<sub>2</sub>S as a Recyclable
 Nanocatalyst for Oxidative Amination of N, N-Dimethylbenzylamines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3226
_journal_page_last               3235
_journal_paper_doi               10.1021/acs.joc.8b00107
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H17 Br N4'
_chemical_formula_sum            'C17 H17 Br N4'
_chemical_formula_weight         357.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.02(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.62(3)
_cell_length_b                   5.811(16)
_cell_length_c                   28.80(7)
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.26
_cell_volume                     1594(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1319
_diffrn_reflns_av_unetI/netI     0.1711
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            5721
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.581
_exptl_absorpt_correction_T_max  0.474
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2014)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5590
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1851
_refine_ls_R_factor_gt           0.0916
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+1.0454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1970
_refine_ls_wR_factor_ref         0.2383
_reflns_Friedel_coverage         0.507
_reflns_Friedel_fraction_full    0.622
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                2459
_reflns_number_total             5590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00107_si_001.cif
_cod_data_source_block           3n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Monoclinic' changed to
'monoclinic' according to
/home/data/users/saulius/crontab/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033531--4033532.cif.
;
_cod_database_code               4033532
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              6114
_shelx_hkl_checksum              95020