Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale
Banwell, Martin G.; Liu, Xin; Connal, Luke A.; Gardiner, Michael G.; Macromolecules  (2020) –; doi:10.1021/acs.macromol.0c01305

data_1558460
_publ_section_title
;
 Synthesis of Functionally and Stereochemically Diverse Polymers via
 Ring-Opening Metathesis Polymerization of Derivatives of the
 Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial
 Scale
;
_journal_name_full               Macromolecules
_journal_paper_doi               10.1021/acs.macromol.0c01305
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H14 O3, 0.25(H2 O)'
_chemical_formula_sum            'C11 H14.5 O3.25'
_chemical_formula_weight         198.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6764(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.90591(5)
_cell_length_b                   16.31586(14)
_cell_length_c                   19.97540(17)
_cell_measurement_reflns_used    22975
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.7740
_cell_measurement_theta_min      4.4190
_cell_volume                     1924.01(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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    -54.00  30.00   1.00    4.00    --  -36.95  57.00  30.00   84
  2  \w    -66.00  34.00   1.00    4.00    --  -36.95  19.00  90.00  100
  3  \w    -54.00  30.00   1.00    4.00    --  -36.95  57.00-150.00   84
  4  \w      4.00  30.00   1.00    4.00    --   36.95  88.00 -17.44   26
  5  \w      3.00  29.00   1.00    4.00    --   36.95  90.00 102.41   26
  6  \w     27.00  90.00   1.00    4.00    --   36.95-125.00 -60.00   63
  7  \w      9.00  42.00   1.00    4.00    --   36.95  79.00  62.25   33
  8  \w    -30.00  54.00   1.00    4.00    --   36.95 -57.00 150.00   84
  9  \w    -32.00  56.00   1.00    4.00    --   36.95 -38.00 -90.00   88
 10  \w    -32.00  56.00   1.00    4.00    --   36.95 -38.00  60.00   88
 11  \w    -34.00  66.00   1.00    4.00    --   36.95 -19.00-180.00  100
 12  \w     18.00 106.00   1.00    4.00    --   36.95  38.00 -30.00   88
 13  \w      7.00  36.00   1.00    4.00    --   36.95  82.00-175.02   29
 14  \w      3.00  29.00   1.00    4.00    --   36.95  90.00-102.00   26
 15  \w      6.00  76.00   1.00    4.00    --   36.95 -99.00   0.00   70
 16  \w     42.00 130.00   1.00   19.00    --  111.00 -38.00-120.00   88
 17  \w    103.00 178.00   1.00   19.00    --  111.00  77.00 150.00   75
 18  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00 150.00   64
 19  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00 -60.00   64
 20  \w     43.00 128.00   1.00   19.00    --  111.00 -50.00 -30.00   85
 21  \w     42.00 178.00   1.00   19.00    --  111.00   0.00-120.00  136
 22  \w     41.00 136.00   1.00   19.00    --  111.00 -25.00 -30.00   95
 23  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00  60.00   64
 24  \w     41.00 109.00   1.00   19.00    --  111.00-111.00 -30.00   68
 25  \w     41.00 157.00   1.00   19.00    --  111.00 -12.00 -30.00  116
 26  \w     43.00 128.00   1.00   19.00    --  111.00 -54.00  51.48   85
 27  \w     61.00 146.00   1.00   19.00    --  111.00 178.00-150.00   85
 28  \w     91.00 178.00   1.00   19.00    --  111.00  64.00-180.00   87
 29  \w     43.00 138.00   1.00   19.00    --  111.00 -77.00  90.00   95
 30  \w     41.00 109.00   1.00   19.00    --  111.00-111.00 -90.00   68
 31  \w    104.00 178.00   1.00   19.00    --  111.00 111.00  30.00   74
 32  \w     86.00 178.00   1.00   19.00    --  111.00  25.00-150.00   92
 33  \w     41.00 136.00   1.00   19.00    --  111.00 -25.00  60.00   95
 34  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00-180.00   64
 35  \w     41.00 109.00   1.00   19.00    --  111.00-111.00 -60.00   68
 36  \w     43.00 138.00   1.00   19.00    --  111.00 -77.00 -30.00   95
 37  \w    103.00 178.00   1.00   19.00    --  111.00  77.00-150.00   75
 38  \w     91.00 178.00   1.00   19.00    --  111.00  64.00 -60.00   87
 39  \w     94.00 178.00   1.00   19.00    --  111.00  50.00 -90.00   84
 40  \w    103.00 178.00   1.00   19.00    --  111.00  77.00  90.00   75
 41  \w     43.00 128.00   1.00   19.00    --  111.00 -50.00 120.00   85
 42  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00   0.00   64
 43  \w     42.00 106.00   1.00   19.00    --  111.00 -92.00  90.00   64
 44  \w     41.00 109.00   1.00   19.00    --  111.00-111.00  90.00   68
 45  \w     41.00 109.00   1.00   19.00    --  111.00-111.00   0.00   68
 46  \w    104.00 178.00   1.00   19.00    --  111.00 111.00  90.00   74
 47  \w    103.00 178.00   1.00   19.00    --  111.00  77.00   0.00   75
 48  \w     41.00 109.00   1.00   19.00    --  111.00-111.00 150.00   68
 49  \w     41.00 157.00   1.00   19.00    --  111.00 -12.00  60.00  116
 50  \w     43.00  91.00   1.00   19.00    --  111.00 -50.00-180.00   48
 51  \w     85.00 127.00   1.00   19.00    --  111.00 -50.00 150.00   42
 52  \w     78.00 104.00   1.00   19.00    --  111.00 -38.00   0.00   26
 53  \w    112.00 176.00   1.00   19.00    --  111.00  25.00  30.00   64
 54  \w     93.00 119.00   1.00   19.00    --  111.00 -77.00 120.00   26
 55  \w     85.00 129.00   1.00   19.00    --  111.00 -67.00 -75.09   44
 56  \w     47.00  73.00   1.00   19.00    --  111.00 -67.00 -75.09   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1306994000
_diffrn_orient_matrix_UB_12      0.0775729000
_diffrn_orient_matrix_UB_13      -0.0221761000
_diffrn_orient_matrix_UB_21      -0.2055678000
_diffrn_orient_matrix_UB_22      -0.0531600000
_diffrn_orient_matrix_UB_23      -0.0210053000
_diffrn_orient_matrix_UB_31      -0.0932094000
_diffrn_orient_matrix_UB_32      0.0084602000
_diffrn_orient_matrix_UB_33      0.0709008000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.949
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (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    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         7774
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0368P)^2^+0.1877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7576
_reflns_number_total             7774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ma0c01305_si_003.cif
_cod_data_source_block           xl-4-148-2scaled
_cod_original_formula_sum        'C11 H14.50 O3.25'
_cod_database_code               1558460
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C11H14.5O3.25
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C2(H2), C3(H3A), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
;
_shelx_res_checksum              92599
_shelx_hkl_checksum              54694
_ins_header
;
TITL XL-4-148-2scaled in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   5.905912  16.315864  19.975403  90.0000  91.6764  90.0000
ZERR    8.00   0.000047   0.000144   0.000169   0.0000   0.0007   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H O
UNIT 88.00 116.00 26.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-09-17
_olex2_date_sample_submission    2019-09-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder with oil'
_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 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.863