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_1558462
_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'
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22
_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             2019-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.5290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.96540(10)
_cell_length_b                   9.08400(10)
_cell_length_c                   10.66780(10)
_cell_measurement_reflns_used    11770
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6870
_cell_measurement_theta_min      4.3240
_cell_volume                     920.867(17)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -102.00 -16.00   1.00    1.00    --  -36.95 146.00 101.00   86
  2  \w    -64.00  31.00   1.00    1.00    --  -36.95  77.00 120.00   95
  3  \w     20.00 104.00   1.00    1.00    --   36.95  57.00  60.00   84
  4  \w      4.00  30.00   1.00    1.00    --   36.95  88.00 -66.85   26
  5  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00-150.00   88
  6  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00  60.00   88
  7  \w      7.00  36.00   1.00    1.00    --   36.95  82.00  17.37   29
  8  \w     18.00 106.00   1.00    1.00    --   36.95  38.00   0.00   88
  9  \w     20.00 104.00   1.00    1.00    --   36.95  57.00 -30.00   84
 10  \w     20.00 104.00   1.00    1.00    --   36.95  57.00 150.00   84
 11  \w     42.00 106.00   1.00    2.00    --  111.00 -92.00-120.00   64
 12  \w     41.00 109.00   1.00    2.00    --  111.00-111.00-180.00   68
 13  \w     94.00 178.00   1.00    2.00    --  111.00  50.00 150.00   84
 14  \w     91.00 178.00   1.00    2.00    --  111.00  64.00 -60.00   87
 15  \w    103.00 178.00   1.00    2.00    --  111.00  77.00  90.00   75
 16  \w     41.00 109.00   1.00    2.00    --  111.00-111.00 120.00   68
 17  \w     41.00 134.00   1.00    2.00    --  111.00 -26.00 159.49   93
 18  \w     42.00 106.00   1.00    2.00    --  111.00 -92.00 -30.00   64
 19  \w    104.00 178.00   1.00    2.00    --  111.00 111.00 -90.00   74
 20  \w     91.00 178.00   1.00    2.00    --  111.00  64.00-120.00   87
 21  \w     42.00 106.00   1.00    2.00    --  111.00 -92.00-150.00   64
 22  \w     41.00 108.00   1.00    2.00    --  111.00-105.00 -62.00   67
 23  \w     42.00 130.00   1.00    2.00    --  111.00 -38.00-120.00   88
 24  \w     44.00 131.00   1.00    2.00    --  111.00 -64.00-150.00   87
 25  \w     86.00 178.00   1.00    2.00    --  111.00  25.00  60.00   92
 26  \w     91.00 178.00   1.00    2.00    --  111.00  64.00 -30.00   87
 27  \w    104.00 178.00   1.00    2.00    --  111.00 111.00-180.00   74
 28  \w     42.00 106.00   1.00    2.00    --  111.00 -92.00  30.00   64
 29  \w     42.00 106.00   1.00    2.00    --  111.00 -92.00-180.00   64
 30  \w     41.00 109.00   1.00    2.00    --  111.00-111.00 -90.00   68
 31  \w     92.00 178.00   1.00    2.00    --  111.00  38.00   0.00   86
 32  \w     41.00 109.00   1.00    2.00    --  111.00-111.00  30.00   68
 33  \w     91.00 178.00   1.00    2.00    --  111.00  64.00 -90.00   87
 34  \w     42.00 130.00   1.00    2.00    --  111.00 -38.00   0.00   88
 35  \w     41.00 109.00   1.00    2.00    --  111.00-111.00-150.00   68
 36  \w     41.00 109.00   1.00    2.00    --  111.00-111.00  90.00   68
 37  \w     43.00 139.00   1.00    2.00    --  111.00 -80.00 -92.56   96
 38  \w    104.00 178.00   1.00    2.00    --  111.00 111.00  60.00   74
 39  \w     61.00 146.00   1.00    2.00    --  111.00 178.00-120.00   85
 40  \w     86.00 178.00   1.00    2.00    --  111.00  25.00-120.00   92
 41  \w    -32.00  56.00   1.00    1.00    --   36.95 -38.00 -30.00   88
 42  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-150.00   84
 43  \w      5.00  31.00   1.00    1.00    --   36.95  87.00-125.06   26
 44  \w     37.00 103.00   1.00    1.00    --   36.95-146.00  50.00   66
 45  \w      4.00  30.00   1.00    1.00    --   36.95  88.00-172.16   26
 46  \w     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
 47  \w      5.00  31.00   1.00    1.00    --   36.95  86.00 104.29   26
 48  \w      5.00  31.00   1.00    1.00    --   36.95  87.00  73.01   26
 49  \w      3.00  29.00   1.00    1.00    --   36.95  90.00 147.94   26
 50  \w     18.00 106.00   1.00    1.00    --   36.95  38.00-150.00   88
 51  \w    -34.00  66.00   1.00    1.00    --   36.95 -19.00-150.00  100
 52  \w     94.00 178.00   1.00    2.00    --  111.00  50.00-180.00   84
 53  \w     86.00 178.00   1.00    2.00    --  111.00  25.00 120.00   92
 54  \w     91.00 178.00   1.00    2.00    --  111.00  64.00  60.00   87
;
_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      -0.0091384000
_diffrn_orient_matrix_UB_12      0.0408609000
_diffrn_orient_matrix_UB_13      -0.1424863000
_diffrn_orient_matrix_UB_21      -0.0096058000
_diffrn_orient_matrix_UB_22      0.1641299000
_diffrn_orient_matrix_UB_23      0.0325436000
_diffrn_orient_matrix_UB_31      0.1616072000
_diffrn_orient_matrix_UB_32      0.0121058000
_diffrn_orient_matrix_UB_33      0.0397222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.817
_diffrn_reflns_theta_min         4.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0403P)^2^+0.1007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3642
_reflns_number_total             3724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ma0c01305_si_004.cif
_cod_data_source_block           xl-4-148-1scaledanal
_cod_database_code               1558462
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C11H14O3
_reflns_odcompleteness_completeness 98.71
_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:
 C13(H13), C14(H14), C15(H15), C18(H18), C20(H20), C21(H21), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17)
;
_shelx_res_checksum              92828
_shelx_hkl_checksum              54798
_ins_header
;
TITL XL-4-148-1scaledanal in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   9.965369   9.083993  10.667822  90.0000 107.5291  90.0000
ZERR    4.00   0.000091   0.000074   0.000105   0.0000   0.0011   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H O
UNIT 44.00 56.00 12.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-09-20
_olex2_date_sample_submission    2019-09-19
_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 1.197
_oxdiff_exptl_absorpt_empirical_full_min 0.867