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_7232951
_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 H13 Br N2 O5 S'
_chemical_formula_sum            'C12 H13 Br N2 O5 S'
_chemical_formula_weight         377.21
_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.cc2198zm
_audit_creation_date             2018-10-09
_audit_creation_method
;
Olex2 1.2-beta
(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                 105.550(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4406(6)
_cell_length_b                   12.7982(11)
_cell_length_c                   14.3406(11)
_cell_measurement_reflns_used    1758
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.8830
_cell_measurement_theta_min      3.6650
_cell_volume                     1492.4(2)
_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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.839
_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    -14.00  12.00   1.00    7.50    --   15.49 -38.00 120.00   26
  2  \w    -20.00  23.00   1.00    7.50    --  -16.12 -99.00 120.00   43
  3  \w     -3.00  82.00   1.00    7.50    --   15.49  38.00 150.00   85
  4  \w    -37.00  38.00   1.00    7.50    --  -16.12  77.00   0.00   75
;
_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      0.0680936000
_diffrn_orient_matrix_UB_12      -0.0127796000
_diffrn_orient_matrix_UB_13      0.0394872000
_diffrn_orient_matrix_UB_21      -0.0142564000
_diffrn_orient_matrix_UB_22      -0.0538224000
_diffrn_orient_matrix_UB_23      -0.0105552000
_diffrn_orient_matrix_UB_31      0.0527605000
_diffrn_orient_matrix_UB_32      0.0019854000
_diffrn_orient_matrix_UB_33      -0.0310756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7339
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.285
_diffrn_reflns_theta_min         3.351
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60038
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0369P)^2^+1.3078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2197
_reflns_number_total             3418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra03403j2.cif
_cod_data_source_block           exp_5932
_cod_database_code               7232951
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.759
_shelx_estimated_absorpt_t_min   0.686
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C3(H3)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              57002
_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.714