Quick construction of a C–N bond from arylsulfonyl hydrazides and Csp2–X compounds promoted by DMAP at room temperature
Yang, Kai; Gao, Juan-Juan; Luo, Shi-He; Wu, Han-Qing; Pang, Chu-Ming; Wang, Bo-Wen; Chen, Xiao-Yun; Wang, Zhao-Yang; RSC Advances 9 (2019) 19917–; doi:10.1039/C9RA03403J

data_7232952
_publ_section_title
;
 Quick construction of a C--N bond from arylsulfonyl hydrazides and
 Csp2--X compounds promoted by DMAP at room temperature
;
_journal_issue                   35
_journal_name_full               'RSC Advances'
_journal_page_first              19917
_journal_paper_doi               10.1039/C9RA03403J
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C12 H14 Br N2 O3, Br'
_chemical_formula_sum            'C12 H14 Br2 N2 O3'
_chemical_formula_weight         394.07
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc21990p
_audit_creation_date             2018-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-18 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.975(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8741(11)
_cell_length_b                   7.9880(12)
_cell_length_c                   21.034(3)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3730
_cell_measurement_theta_min      4.3250
_cell_volume                     1480.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -21.00  23.00   1.00    7.50    --  -16.28 -99.00-120.00   44
  2  \w     -5.00  20.00   1.00    7.50    --   15.49-106.00  48.00   25
  3  \w    -19.00   6.00   1.00    7.50    --  -16.28-106.00  48.00   25
  4  \w    -25.00  23.00   1.00    7.50    --  -16.28 -99.00 150.00   48
  5  \w     23.00  77.00   1.00    7.50    --   15.49  57.00 150.00   54
  6  \w     36.00  87.00   1.00    7.50    --   15.49 178.00   0.00   51
  7  \w     45.00  86.00   1.00    7.50    --   15.49 178.00  60.00   41
  8  \w    -28.00  -3.00   1.00    7.50    --  -16.28 106.00 147.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713598000
_diffrn_orient_matrix_UB_12      0.0408703000
_diffrn_orient_matrix_UB_13      0.0046201000
_diffrn_orient_matrix_UB_21      -0.0090756000
_diffrn_orient_matrix_UB_22      0.0247798000
_diffrn_orient_matrix_UB_23      -0.0326403000
_diffrn_orient_matrix_UB_31      -0.0359662000
_diffrn_orient_matrix_UB_32      0.0749377000
_diffrn_orient_matrix_UB_33      0.0082345000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.1140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9145
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         3.501
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.249
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1367
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1663
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra03403j2.cif
_cod_data_source_block           exp_6083
_cod_original_cell_volume        1480.0(3)
_cod_database_code               7232952
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.584
_shelx_estimated_absorpt_t_min   0.273
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Br1-Br2
 4 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C6(H6), C9(H9)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              12621
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.984
_oxdiff_exptl_absorpt_empirical_full_min 0.522