Synthesis of Functionalized Cyclic Carbonates through Commodity Polymer Upcycling
Jehanno, Coralie; Demarteau, Jeremy; Mantione, Daniele; Arno, Maria C.; Ruipérez, Fernando; Hedrick, James L.; Dove, Andrew P.; Sardon, Haritz; ACS Macro Letters  (2020) 443–447; doi:10.1021/acsmacrolett.0c00164

data_4517498
_publ_section_title
;
 Synthesis of Functionalized Cyclic Carbonates through Commodity Polymer
 Upcycling
;
_journal_name_full               'ACS Macro Letters'
_journal_page_first              443
_journal_page_last               447
_journal_paper_doi               10.1021/acsmacrolett.0c00164
_journal_year                    2020
_chemical_formula_moiety         'C H3 O3 S, C7 H14 N3'
_chemical_formula_sum            'C8 H17 N3 O3 S'
_chemical_formula_weight         235.30
_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             2018-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5738(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.83127(10)
_cell_length_b                   16.36158(17)
_cell_length_c                   8.81821(11)
_cell_measurement_reflns_used    10961
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9560
_cell_measurement_theta_min      5.1840
_cell_volume                     1093.54(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_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   -118.00  -9.00   1.00    2.50    --  -42.09 -77.00  90.00  109
  2  \w    -83.00  38.00   1.00    2.50    --  -42.09  19.00 150.00  121
  3  \w    -34.00  75.00   1.00    2.50    --   42.09 -77.00-120.00  109
  4  \w     18.00  98.00   1.00    2.50    --   42.09-125.00 120.00   80
  5  \w     18.00 116.00   1.00    2.50    --   42.09  38.00 -90.00   98
  6  \w     32.00 109.00   1.00   10.00    --  114.00 -95.00 -60.00   77
  7  \w     38.00 116.00   1.00   10.00    --  114.00-111.00  60.00   78
  8  \w     42.00 143.00   1.00   10.00    --  114.00 -61.00 -30.00  101
  9  \w     86.00 178.00   1.00   10.00    --  114.00  30.00  60.00   92
 10  \w     88.00 178.00   1.00   10.00    --  114.00  45.00 150.00   90
 11  \w     38.00 147.00   1.00   10.00    --  114.00 -77.00-150.00  109
 12  \w     32.00 109.00   1.00   10.00    --  114.00 -95.00 150.00   77
 13  \w     38.00 142.00   1.00   10.00    --  114.00 -30.00  60.00  104
 14  \w    100.00 178.00   1.00   10.00    --  114.00 111.00-180.00   78
 15  \w     38.00 116.00   1.00   10.00    --  114.00-111.00 120.00   78
 16  \w     41.00 140.00   1.00   10.00    --  114.00 -45.00 120.00   99
 17  \w     86.00 178.00   1.00   10.00    --  114.00  30.00 -60.00   92
 18  \w   -114.00 -14.00   1.00    2.50    --  -42.09 -57.00 150.00  100
 19  \w   -114.00 -14.00   1.00    2.50    --  -42.09 -57.00 -30.00  100
 20  \w   -118.00  -9.00   1.00    2.50    --  -42.09 -77.00 -90.00  109
 21  \w     -4.00  83.00   1.00    2.50    --   42.09 -99.00-180.00   87
 22  \w    -30.00  70.00   1.00    2.50    --   42.09 -57.00 -60.00  100
 23  \w     81.00 178.00   1.00   10.00    --  114.00  77.00  90.00   97
 24  \w     85.00 135.00   1.00   10.00    --  114.00  61.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0788348000
_diffrn_orient_matrix_UB_12      0.0805121000
_diffrn_orient_matrix_UB_13      -0.0426338000
_diffrn_orient_matrix_UB_21      -0.1660942000
_diffrn_orient_matrix_UB_22      0.0462945000
_diffrn_orient_matrix_UB_23      0.0151757000
_diffrn_orient_matrix_UB_31      0.0865809000
_diffrn_orient_matrix_UB_32      0.0155636000
_diffrn_orient_matrix_UB_33      0.1747863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14156
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.476
_diffrn_reflns_theta_min         5.407
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0593P)^2^+0.4768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2252
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mz0c00164_si_002.cif
_cod_data_source_block           dm3
_cod_depositor_comments          'Adding full bibliography for 4517498.cif.'
_cod_database_code               4517498
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
The NHs were located in a difference map but placed at calculated positions for the refinement.

1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              58460
_shelx_hkl_checksum              53581
_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 2.578
_oxdiff_exptl_absorpt_empirical_full_min 0.764