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_1571548
_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         'C26 H44 N2 O4 S4'
_chemical_formula_sum            'C26 H44 N2 O4 S4'
_chemical_formula_weight         576.87
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-08 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.725(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9546(4)
_cell_length_b                   20.1055(6)
_cell_length_c                   11.0995(3)
_cell_measurement_reflns_used    24029
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      75.2700
_cell_measurement_theta_min      3.2180
_cell_volume                     3049.14(15)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_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      99.99(13)
_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 0.977
_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    -44.00  23.00   0.50    1.01    --  -49.22  42.00 144.00  134
  2  \w   -120.00 -40.00   0.50    1.01    --  -49.22 -42.00  -7.00  160
  3  \w     41.00 121.00   0.50    1.01    --   49.22  42.00 144.00  160
  4  \w    -22.00  54.00   0.50    1.01    --   49.22 -42.00  -7.00  152
  5  \w     92.00 174.00   0.50    4.03    --  101.75  42.00 144.00  164
  6  \w   -158.00-133.00   0.50    4.03    -- -103.00 -42.00  -7.00   50
  7  \w    -29.00  19.00   0.50    1.01    --  -49.22  19.00-120.00   96
  8  \w   -117.00 -79.00   0.50    1.01    --  -49.22-125.00-180.00   76
  9  \w    -93.00 -13.00   0.50    1.01    --  -49.22 125.00  30.00  160
 10  \w     83.00 120.00   0.50    1.01    --   49.22  57.00 -60.00   74
 11  \w     29.00 120.00   0.50    1.01    --   49.22  77.00-120.00  182
 12  \w     39.00  79.00   0.50    1.01    --   49.22  57.00 -60.00   80
 13  \w     56.00  84.00   0.50    1.01    --   49.22  57.00-120.00   56
 14  \w    -22.00  24.00   0.50    1.01    --   49.22 -19.00-150.00   92
 15  \w     49.00 102.00   0.50    1.01    --   49.22  37.00-150.00  106
 16  \w     33.00  64.00   0.50    4.03    --  101.75 -61.00-150.00   62
 17  \w     30.00  75.00   0.50    4.03    --  101.75 -61.00  60.00   90
 18  \w     93.00 131.00   0.50    4.03    --  101.75  45.00-120.00   76
 19  \w     88.00 117.00   0.50    4.03    --  101.75  61.00-120.00   58
 20  \w     34.00  72.00   0.50    4.03    --  101.75 -61.00-120.00   76
 21  \w    120.00 171.00   0.50    4.03    --  101.75  61.00 -90.00  102
 22  \w     30.00  55.00   0.50    4.03    --  101.75 -45.00 150.00   50
 23  \w     89.00 121.00   0.50    4.03    --  101.75  61.00 -60.00   64
 24  \w     81.00 106.00   0.50    4.03    --  101.75  77.00 -90.00   50
 25  \w     81.00 107.00   0.50    4.03    --  101.75  77.00-120.00   52
 26  \w     88.00 113.00   0.50    4.03    --  101.75  61.00-150.00   50
 27  \w    138.00 164.00   0.50    4.03    --  101.75  77.00-120.00   52
 28  \w     93.00 174.00   0.50    4.03    --  101.75  45.00 -60.00  162
 29  \w     81.00 106.00   0.50    4.03    --  101.75  77.00-150.00   50
 30  \w     94.00 173.00   0.50    4.03    --  101.75  15.00 120.00  158
 31  \w     81.00 170.00   0.50    4.03    --  101.75 125.00   0.00  178
 32  \w     31.00  75.00   0.50    4.03    --  101.75 -61.00 150.00   88
 33  \w     44.00  75.00   0.50    4.03    --  101.75 -61.00 -90.00   62
 34  \w     81.00 109.00   0.50    4.03    --  101.75  77.00-180.00   56
 35  \w     32.00  57.00   0.50    4.03    --  101.75 -45.00-120.00   50
 36  \w     30.00  56.00   0.50    4.03    --  101.75 -45.00-150.00   52
 37  \w    109.00 135.00   0.50    4.03    --  101.75  45.00-180.00   52
 38  \w    123.00 168.00   0.50    4.03    --  101.75  30.00  90.00   90
 39  \w     30.00  61.00   0.50    4.03    --  101.75 -77.00  90.00   62
 40  \w     65.00  91.00   0.50    4.03    --  101.75 -77.00  90.00   52
 41  \w     88.00 114.00   0.50    4.03    --  101.75  61.00 -90.00   52
 42  \w   -123.00 -88.00   0.50    4.03    -- -103.00 -62.00-115.61   70
 43  \w   -115.00 -89.00   0.50    4.03    -- -103.00 -59.00-145.65   52
 44  \w   -105.00 -79.00   0.50    4.03    -- -103.00 -84.00 -66.15   52
 45  \w   -107.00 -80.00   0.50    4.03    -- -103.00 -82.00 -97.91   54
 46  \w   -114.00 -87.00   0.50    4.03    -- -103.00 -64.00-145.29   54
 47  \w   -117.00 -91.00   0.50    4.03    -- -103.00 -60.00 -74.70   52
 48  \w   -116.00 -89.00   0.50    4.03    -- -103.00 -61.00 -60.00   54
 49  \w   -117.00 -90.00   0.50    4.03    -- -103.00 -57.00 -60.68   54
 50  \w    -92.00 -31.00   0.50    4.03    -- -103.00  77.00  30.00  122
 51  \w   -108.00 -82.00   0.50    4.03    -- -103.00 -77.00 -60.00   52
 52  \w   -109.00 -82.00   0.50    4.03    -- -103.00 -77.00 -90.00   54
 53  \w   -110.00 -84.00   0.50    4.03    -- -103.00 -73.00-106.40   52
 54  \w   -169.00 -87.00   0.50    4.03    -- -103.00 -64.00 -93.21  164
 55  \w   -171.00 -87.00   0.50    4.03    -- -103.00 -64.00-100.93  168
 56  \w   -130.00 -96.00   0.50    4.03    -- -103.00 -61.00-150.00   68
 57  \w   -174.00-138.00   0.50    4.03    -- -103.00 -61.00-150.00   72
 58  \w    -57.00 -32.00   0.50    4.03    -- -103.00  61.00 -60.00   50
 59  \w   -109.00 -84.00   0.50    4.03    -- -103.00 -73.00 -55.28   50
 60  \w   -116.00 -89.00   0.50    4.03    -- -103.00 -62.00 -81.93   54
 61  \w   -169.00-128.00   0.50    4.03    -- -103.00 -73.00 -55.28   82
 62  \w   -107.00 -82.00   0.50    4.03    -- -103.00 -77.00-120.00   50
 63  \w   -173.00-119.00   0.50    4.03    -- -103.00 -77.00-120.00  108
;
_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      0.1051710000
_diffrn_orient_matrix_UB_12      -0.0148125000
_diffrn_orient_matrix_UB_13      -0.0155469000
_diffrn_orient_matrix_UB_21      -0.0405314000
_diffrn_orient_matrix_UB_22      -0.0373407000
_diffrn_orient_matrix_UB_23      -0.1207424000
_diffrn_orient_matrix_UB_31      0.0004867000
_diffrn_orient_matrix_UB_32      0.0652662000
_diffrn_orient_matrix_UB_33      -0.0725806000
_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  0.0701
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            58595
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.663
_diffrn_reflns_theta_min         3.234
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.089
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0735P)^2^+2.0342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5266
_reflns_number_total             6266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4py00160e2.cif
_cod_data_source_block           cx3245b
_cod_depositor_comments
'Adding full bibliography for 1571547--1571550.cif.'
_cod_database_code               1571548
_shelx_shelxl_version_number     2019/1
_chemical_oxdiff_formula         C26H44N2O4S3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C15(H15A,H15B), C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,
 H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              43221
_shelx_hkl_checksum              30630
_olex2_date_sample_data_collection 2023-10-24
_olex2_date_sample_submission    2023-10-24
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in paratone oil'
_olex2_submission_original_sample_id cx3245b
_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 2.366
_oxdiff_exptl_absorpt_empirical_full_min 0.534