BiTEMPS methacrylate dynamic covalent cross-linker providing rapid reprocessability and extrudability of covalent adaptable networks: high-yield synthesis with strong selectivity for disulfide linkages
Debsharma, Tapas; Purwanto, Nathan S.; Fenimore, Logan M.; Mitchell, Sarah; Kennedy, Jayme; Torkelson, John M.; Polymer Chemistry 15 (2024) 2167–2176; doi:10.1039/D4PY00160E

data_1571549
_publ_section_title
;
 BiTEMPS methacrylate dynamic covalent cross-linker providing rapid
 reprocessability and extrudability of covalent adaptable networks:
 high-yield synthesis with strong selectivity for disulfide linkages
;
_journal_issue                   21
_journal_name_full               'Polymer Chemistry'
_journal_page_first              2167
_journal_page_last               2176
_journal_paper_doi               10.1039/D4PY00160E
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C13 H23 N O2'
_chemical_formula_sum            'C13 H23 N O2'
_chemical_formula_weight         225.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-07 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                89.579(2)
_cell_angle_beta                 78.811(2)
_cell_angle_gamma                86.145(2)
_cell_formula_units_Z            2
_cell_length_a                   6.28690(10)
_cell_length_b                   9.3906(2)
_cell_length_c                   11.5393(2)
_cell_measurement_reflns_used    28215
_cell_measurement_temperature    100.1(3)
_cell_measurement_theta_max      77.1780
_cell_measurement_theta_min      4.6380
_cell_volume                     666.78(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.65a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.65a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.65a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_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    -78.00  25.00   0.50    0.32    --  -47.67  93.00 -92.00  206
  2  \w    -24.00  78.00   0.50    0.32    --   47.67 -93.00 155.00  204
  3  \w   -105.00 -31.00   0.50    1.27    -- -104.00  93.00 -92.00  148
  4  \w   -175.00 -83.50   0.50    1.27    -- -104.00 -93.00 155.00  183
  5  \w     89.00 178.00   0.50    1.27    --  110.25  93.00 -92.00  178
  6  \w   -119.00 -33.00   0.50    0.32    --  -47.67 -57.00  60.00  172
  7  \w   -122.00 -35.00   0.50    0.32    --  -47.67 -19.00 -30.00  174
  8  \w   -119.00 -25.00   0.50    0.32    --  -47.67 -77.00  30.00  188
  9  \w   -119.00 -33.00   0.50    0.32    --  -47.67 -57.00 150.00  172
 10  \w   -119.00 -25.00   0.50    0.32    --  -47.67 -77.00 -60.00  188
 11  \w     33.00 119.00   0.50    0.32    --   47.67  57.00-180.00  172
 12  \w     25.00 119.00   0.50    0.32    --   47.67  77.00-120.00  188
 13  \w     35.00 121.00   0.50    0.32    --   47.67  37.00 150.00  172
 14  \w     31.00 125.00   0.50    0.32    --   52.00  73.00 123.06  188
 15  \w     30.00 125.00   0.50    0.32    --   52.00  75.00 174.16  190
 16  \w     35.00 129.00   0.50    0.32    --   56.00  73.00 137.11  188
 17  \w     35.00 129.00   0.50    0.32    --   56.00  73.00   4.53  188
 18  \w   -132.00 -37.00   0.50    0.32    --  -60.00 -76.00 -94.72  190
 19  \w     38.00 132.00   0.50    0.32    --   60.00  76.00  51.67  188
 20  \w     38.00 132.00   0.50    0.32    --   60.00  75.00 146.19  188
 21  \w     37.00 132.00   0.50    0.32    --   60.00  77.00-137.15  190
 22  \w     43.00 137.00   0.50    0.32    --   64.00  74.00  87.22  188
 23  \w     43.00 137.00   0.50    0.32    --   64.00  72.00  15.25  188
 24  \w     48.00 140.00   0.50    0.32    --   68.00  71.00-178.29  184
 25  \w   -145.00 -52.00   0.50    0.32    --  -72.00 -71.00-114.59  186
 26  \w   -145.00 -54.00   0.50    0.32    --  -72.00 -64.00 -65.59  182
 27  \w   -145.00 -49.00   0.50    0.32    --  -72.00 -76.00  11.61  192
 28  \w   -145.00 -54.00   0.50    0.32    --  -72.00 -65.00 105.96  182
 29  \w     50.00 145.00   0.50    0.32    --   72.00  75.00   7.70  190
 30  \w   -149.00 -53.00   0.50    1.27    --  -76.00 -76.00-151.88  192
 31  \w   -149.00 -54.00   0.50    1.27    --  -76.00 -75.00  93.56  190
 32  \w   -149.00 -55.00   0.50    1.27    --  -76.00 -73.00-176.81  188
 33  \w   -149.00 -59.00   0.50    1.27    --  -76.00 -62.00-101.11  180
 34  \w   -153.00 -59.00   0.50    1.27    --  -80.00 -73.00  67.14  188
 35  \w   -157.00 -63.00   0.50    1.27    --  -84.00 -73.00 -28.14  188
 36  \w   -157.00 -62.00   0.50    1.27    --  -84.00 -74.00  12.38  190
 37  \w   -157.00 -66.00   0.50    1.27    --  -84.00 -66.00  29.02  182
 38  \w   -157.00 -62.00   0.50    1.27    --  -84.00 -75.00-121.50  190
 39  \w   -157.00 -65.00   0.50    1.27    --  -84.00 -68.00 129.16  184
 40  \w   -157.00 -62.00   0.50    1.27    --  -84.00 -74.00 163.18  190
 41  \w   -161.00 -67.00   0.50    1.27    --  -88.00 -72.00  51.45  188
 42  \w   -161.00 -70.00   0.50    1.27    --  -88.00 -66.00 167.98  182
 43  \w   -161.00 -69.00   0.50    1.27    --  -88.00 -68.00 -94.89  184
 44  \w   -161.00 -66.00   0.50    1.27    --  -88.00 -75.00  32.24  190
 45  \w   -165.00 -73.00   0.50    1.27    --  -92.00 -68.00  -7.20  184
 46  \w   -165.00 -74.00   0.50    1.27    --  -92.00 -64.00 113.47  182
 47  \w   -165.00 -75.00   0.50    1.27    --  -92.00 -62.00 -59.83  180
 48  \w   -164.00 -78.00   0.50    1.27    --  -92.00 -52.00  38.52  172
 49  \w   -169.00 -76.00   0.50    1.27    --  -96.00 -69.00 112.91  186
 50  \w   -168.00 -82.00   0.50    1.27    --  -96.00 -53.00-161.94  172
 51  \w   -169.00 -73.00   0.50    1.27    --  -96.00 -76.00  87.96  192
 52  \w   -168.00 -82.00   0.50    1.27    --  -96.00 -50.00-120.09  172
 53  \w    -69.00 -31.00   0.50    1.27    -- -104.00  61.00  60.00   76
 54  \w   -175.00 -80.00   0.50    1.27    -- -104.00 -80.00 177.79  190
 55  \w   -175.00 -81.00   0.50    1.27    -- -104.00 -77.00  32.76  188
 56  \w   -175.00 -88.00   0.50    1.27    -- -104.00 -59.00  47.11  174
 57  \w   -112.00 -34.00   0.50    1.27    -- -104.00 125.00 -30.00  156
 58  \w   -175.00 -79.50   0.50    1.27    -- -104.00 -83.00   7.69  191
 59  \w   -175.00 -79.50   0.50    1.27    -- -104.00 -83.00 -15.38  191
 60  \w   -175.00 -80.00   0.50    1.27    -- -104.00 -79.00 -94.07  190
 61  \w   -175.00 -81.00   0.50    1.27    -- -104.00 -77.00 -60.00  188
 62  \w    -69.00 -31.00   0.50    1.27    -- -104.00  61.00 120.00   76
 63  \w   -175.00 -85.00   0.50    1.27    -- -104.00 -68.00-120.41  180
 64  \w   -175.00 -86.00   0.50    1.27    -- -104.00 -64.00   7.89  178
 65  \w   -175.00 -87.00   0.50    1.27    -- -104.00 -61.00  90.00  176
 66  \w   -175.00 -80.00   0.50    1.27    -- -104.00 -79.00 155.08  190
 67  \w   -175.00 -83.00   0.50    1.27    -- -104.00 -72.00  41.57  184
 68  \w   -175.00 -87.00   0.50    1.27    -- -104.00 -61.00 120.00  176
 69  \w   -175.00 -81.00   0.50    1.27    -- -104.00 -77.00-150.00  188
 70  \w   -175.00 -85.00   0.50    1.27    -- -104.00 -67.00-118.06  180
 71  \w   -175.00 -79.50   0.50    1.27    -- -104.00 -82.00-134.86  191
 72  \w   -175.00 -85.00   0.50    1.27    -- -104.00 -68.00 -59.15  180
 73  \w     41.00 111.00   0.50    1.27    --  110.25-125.00 120.00  140
 74  \w     38.00 108.00   0.50    1.27    --  110.25 -77.00-120.00  140
 75  \w     41.00 111.00   0.50    1.27    --  110.25-125.00  90.00  140
 76  \w     38.00 108.00   0.50    1.27    --  110.25 -77.00 150.00  140
 77  \w     38.00 106.00   0.50    1.27    --  110.25 -94.00  90.00  136
 78  \w     41.00 111.00   0.50    1.27    --  110.25-125.00-180.00  140
 79  \w     41.00 111.00   0.50    1.27    --  110.25-125.00  30.00  140
 80  \w     38.00 106.00   0.50    1.27    --  110.25 -94.00-120.00  136
 81  \w     38.00  73.00   0.50    1.27    --  110.25 -61.00 -30.00   70
 82  \w     88.00 178.00   0.50    1.27    --  110.25  77.00  90.00  180
 83  \w     41.00 111.00   0.50    1.27    --  110.25-125.00 -90.00  140
 84  \w     38.00  73.00   0.50    1.27    --  110.25 -61.00-180.00   70
 85  \w     38.00 106.00   0.50    1.27    --  110.25 -93.00 155.00  136
 86  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00 -30.00  286
 87  \w   -120.00 -35.00   0.50    0.32    --  -47.67 -43.00-121.77  170
 88  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00 -90.00  286
 89  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00 -60.00  286
 90  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00-120.00  286
 91  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00-180.00  286
 92  \w   -119.00  24.00   0.50    0.32    --  -47.67   0.00-150.00  286
 93  \w     25.00 119.00   0.50    0.32    --   47.67  77.00  60.00  188
 94  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00-150.00  288
 95  \w     35.00 121.00   0.50    0.32    --   47.67  37.00 -60.00  172
 96  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00-180.00  288
 97  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00-120.00  288
 98  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00 -90.00  288
 99  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00 -60.00  288
100  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00 120.00  288
101  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00  90.00  288
102  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00  60.00  288
103  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00  30.00  288
104  \w     35.00 121.00   0.50    0.32    --   47.67  37.00  30.00  172
105  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00   0.00  288
106  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00 150.00  288
107  \w    -24.00 120.00   0.50    0.32    --   47.67   0.00 -30.00  288
108  \w     35.00 129.00   0.50    0.32    --   56.00  74.00  97.70  188
109  \w   -132.00 -37.00   0.50    0.32    --  -60.00 -76.00   1.36  190
110  \w     38.00 132.00   0.50    0.32    --   60.00  75.00 -95.17  188
111  \w   -140.00 -48.00   0.50    0.32    --  -68.00 -71.00 -81.84  184
112  \w   -145.00 -52.00   0.50    0.32    --  -72.00 -69.00  94.74  186
113  \w     50.00 145.00   0.50    0.32    --   72.00  76.00 -33.35  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0200099000
_diffrn_orient_matrix_UB_12      0.0916575000
_diffrn_orient_matrix_UB_13      0.1070582000
_diffrn_orient_matrix_UB_21      -0.2203767000
_diffrn_orient_matrix_UB_22      -0.0472066000
_diffrn_orient_matrix_UB_23      0.0667987000
_diffrn_orient_matrix_UB_31      0.1170968000
_diffrn_orient_matrix_UB_32      -0.1280897000
_diffrn_orient_matrix_UB_33      0.0509731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            50438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.723
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.65a (Rigaku Oxford Diffraction, 2022)
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    1.122
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0517P)^2^+0.2453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2580
_reflns_number_total             2769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4py00160e2.cif
_cod_data_source_block           cx2826a
_cod_depositor_comments
'Adding full bibliography for 1571547--1571550.cif.'
_cod_database_code               1571549
_shelx_shelxl_version_number     2019/1
_chemical_oxdiff_formula         C26H44N2O4S2
_olex2_refinement_description
;
1. Restrained distances
 C12-H12B = C12-H12A
 0.98 with sigma of 0.02
;
_shelx_res_checksum              49031
_shelx_hkl_checksum              80338
_olex2_date_sample_data_collection 2022-09-01
_olex2_date_sample_submission    2022-08-31
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_original_sample_id cx2826a
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.464