A bifunctional recyclable Gemini surfactant catalyst for oxidative nitroso Diels–Alder reactions in water
Jia, Longxia; Liu, Hongling; Shi, Weiwei; Xu, Yingru; Sun, Ruihan; Zuo, Jia; Wang, Bin; Huang, Jianjian; Zhong, Fangrui; Wang, Dangui; Green Chemistry 27 (2025) 13885–13892; doi:10.1039/D5GC03912F

data_7251018
_publ_section_title
;
 A bifunctional recyclable Gemini surfactant catalyst for oxidative
 nitroso Diels--Alder reactions in water
;
_journal_issue                   43
_journal_name_full               'Green Chemistry'
_journal_page_first              13885
_journal_page_last               13892
_journal_paper_doi               10.1039/D5GC03912F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C13 H13 Br2 N O2'
_chemical_formula_sum            'C13 H13 Br2 N O2'
_chemical_formula_weight         375.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-09-27 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.9450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.59350(10)
_cell_length_b                   14.81640(10)
_cell_length_c                   9.14230(10)
_cell_measurement_reflns_used    22314
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9260
_cell_measurement_theta_min      4.6010
_cell_volume                     1301.09(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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    -83.00 -38.00   0.50    0.50    --    0.00 -57.00 -30.00   90
  2  \w    -28.00  21.00   0.50    0.50    --    0.00 -57.00 -30.00   98
  3  \w     -2.00  44.00   0.50    0.50    --   24.00  70.00 -42.19   92
  4  \w     86.00 112.00   0.50    0.50    --   24.00  70.00 -42.19   52
  5  \w    -49.00   0.00   0.50    0.50    --   40.00 -43.00-139.48   98
  6  \w      6.00  58.00   0.50    0.50    --   40.00 -43.00-139.48  104
  7  \w     25.00  64.00   0.50    0.50    --   52.00  72.00 159.26   78
  8  \w     25.00  51.00   0.50    0.50    --   52.00  71.00  65.42   52
  9  \w    113.00 141.00   0.50    0.50    --   52.00  71.00  65.42   56
 10  \w     87.00 135.00   0.50    0.50    --   56.00  72.00 -90.31   96
 11  \w     29.00  58.00   0.50    0.50    --   56.00  72.00 -90.31   58
 12  \w     32.00  72.00   0.50    0.50    --   56.00  75.00 -47.01   80
 13  \w     32.00  58.00   0.50    0.50    --   60.00  75.00 -87.00   52
 14  \w     32.00  61.00   0.50    0.50    --   60.00  75.00-154.50   58
 15  \w     87.00 113.00   0.50    0.50    --   64.00  73.00 154.51   52
 16  \w     36.00  64.00   0.50    0.50    --   64.00  74.00 -78.13   56
 17  \w     37.00  66.00   0.50    0.50    --   64.00  75.00  79.57   58
 18  \w     37.00  74.00   0.50    0.50    --   64.00  73.00 154.51   74
 19  \w    122.00 148.00   0.50    0.50    --   64.00  74.00 -78.13   52
 20  \w     40.00  69.00   0.50    0.50    --   68.00  75.00  50.34   58
 21  \w     40.00  65.00   0.50    0.50    --   68.00  75.00 -18.09   50
 22  \w     46.00  72.00   0.50    0.50    --   72.00  75.00   0.40   52
 23  \w     44.00  70.00   0.50    0.50    --   72.00  75.00 164.87   52
 24  \w     88.00 165.00   0.50    0.50    --   76.00  75.00-153.46  154
 25  \w     48.00  85.00   0.50    0.50    --   76.00  75.00-153.46   74
 26  \w     53.00  93.00   0.50    0.50    --   76.00  61.00  54.14   80
 27  \w     49.00  77.00   0.50    0.50    --   76.00  75.00  88.47   56
 28  \w    122.00 148.00   0.50    0.50    --   80.00  69.00-177.97   52
 29  \w     90.00 116.00   0.50    0.50    --   80.00  69.00-177.97   52
 30  \w     54.00  83.00   0.50    0.50    --   80.00  69.00-177.97   58
 31  \w    129.00 173.00   0.50    0.50    --   84.00  63.00-127.72   88
 32  \w     60.00  86.00   0.50    0.50    --   84.00  63.00-127.72   52
 33  \w     72.00 177.00   0.50    0.50    --   95.80  59.00 110.37  210
 34  \w     77.00 157.00   0.50    0.50    --   95.80  61.00 -60.00  160
 35  \w     74.00 121.00   0.50    0.50    --   95.80  61.00-180.00   94
 36  \w     80.00 112.00   0.50    0.50    --   95.80 -82.00 150.00   64
 37  \w     71.00 184.00   0.50    0.50    --   95.80  64.00  41.04  226
 38  \w     18.00  60.00   0.50    0.50    --   95.80 -82.00 150.00   84
 39  \w      7.00  75.00   0.50    0.50    --   95.80 -82.00-180.00  136
 40  \w     76.00 180.00   0.50    0.50    --   95.80  61.00  60.00  208
 41  \w     35.00 100.00   0.50    0.50    --   95.80 -77.00 -30.00  130
 42  \w    147.00 182.00   0.50    0.50    --   95.80  61.00-120.00   70
 43  \w      8.00  33.00   0.50    0.50    --   95.80 -77.00 -30.00   50
 44  \w     77.00 111.00   0.50    0.50    --   95.80  61.00-120.00   68
 45  \w     73.00  98.00   0.50    0.50    --   95.80  61.00  90.00   50
 46  \w     75.00 155.00   0.50    0.50    --   95.80  61.00 120.00  160
 47  \w     50.00 122.00   0.50    0.50    --   95.80 -82.00 -90.00  144
 48  \w     81.00 171.00   0.50    0.50    --   95.80  45.00  30.00  180
 49  \w     68.00 125.00   0.50    0.50    --   95.80 -82.00  30.00  114
 50  \w      7.00  64.00   0.50    0.50    --   95.80 -82.00  30.00  114
 51  \w     68.00 114.00   0.50    0.50    --   95.80  72.00 -83.76   92
 52  \w    123.00 164.00   0.50    0.50    --   95.80  15.00-120.00   82
 53  \w     72.00 117.00   0.50    0.50    --   95.80  15.00-120.00   90
 54  \w     72.00 110.00   0.50    0.50    --   95.80  61.00  -6.06   76
 55  \w      7.00 117.00   0.50    0.50    --   95.80 -61.00-180.00  220
 56  \w      6.00 108.00   0.50    0.50    --   95.80 -61.00  30.00  204
 57  \w     73.00 101.00   0.50    0.50    --   95.80  61.00 -90.00   56
 58  \w    154.00 179.00   0.50    0.50    --   95.80  61.00 -90.00   50
 59  \w     72.00 144.00   0.50    0.50    --   95.80  61.00 -30.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0188225000
_diffrn_orient_matrix_UB_12      -0.0988725000
_diffrn_orient_matrix_UB_13      -0.0387567000
_diffrn_orient_matrix_UB_21      0.0247686000
_diffrn_orient_matrix_UB_22      0.0313668000
_diffrn_orient_matrix_UB_23      -0.1464670000
_diffrn_orient_matrix_UB_31      0.1573897000
_diffrn_orient_matrix_UB_32      0.0068756000
_diffrn_orient_matrix_UB_33      0.1076595000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28471
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.387
_diffrn_reflns_theta_min         4.604
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (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    1.915
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0222
_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^)+(0.0314P)^2^+1.3855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2583
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc03912f2.cif
_cod_data_source_block           20250926_dg-zbr
_cod_depositor_comments          'Adding full bibliography for 7251018.cif.'
_cod_database_code               7251018
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.572
_shelx_estimated_absorpt_t_min   0.452
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C4(H4), C3(H3), C2(H2)
;
_shelx_res_checksum              9709
_shelx_hkl_checksum              9484
_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 6.410
_oxdiff_exptl_absorpt_empirical_full_min 0.450