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_1558461
_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 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.94700(10)
_cell_length_b                   7.51010(10)
_cell_length_c                   17.0105(3)
_cell_measurement_reflns_used    2673
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9420
_cell_measurement_theta_min      5.1900
_cell_volume                     887.48(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.993
_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 -21.00   0.50    0.50    --  -36.66 -57.00 -60.00  162
  2  \w    -29.00  64.00   0.50    0.50    --   36.66 -19.00 120.00  186
  3  \w     33.00  88.00   0.50    0.50    --   36.66-125.00-150.00  110
  4  \w     98.00 127.00   0.50    2.11    --  111.00 -45.00  90.00   58
  5  \w     63.00 103.00   0.50    2.11    --  111.00 -95.00-180.00   80
  6  \w     62.00  91.00   0.50    2.11    --  111.00-111.00-120.00   58
  7  \w    138.00 166.00   0.50    2.11    --  111.00  30.00  60.00   56
  8  \w     90.00 125.00   0.50    2.11    --  111.00 -15.00-150.00   70
  9  \w    103.00 132.00   0.50    2.11    --  111.00 -30.00 120.00   58
 10  \w     68.00 100.00   0.50    2.11    --  111.00-111.00 -90.00   64
 11  \w     61.00 106.00   0.50    2.11    --  111.00 -95.00 120.00   90
 12  \w     96.00 145.00   0.50    2.11    --  111.00  45.00-180.00   98
 13  \w     40.00  88.00   0.50    2.11    --  111.00 -15.00-150.00   96
 14  \w     46.00  72.00   0.50    2.11    --  111.00 -30.00 120.00   52
 15  \w     93.00 131.00   0.50    2.11    --  111.00  30.00  60.00   76
 16  \w     44.00 125.00   0.50    2.11    --  111.00 -45.00-180.00  162
 17  \w     44.00  95.00   0.50    2.11    --  111.00 -45.00  90.00  102
;
_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      -0.0846523000
_diffrn_orient_matrix_UB_12      0.1893019000
_diffrn_orient_matrix_UB_13      0.0044795000
_diffrn_orient_matrix_UB_21      0.2046391000
_diffrn_orient_matrix_UB_22      0.0780400000
_diffrn_orient_matrix_UB_23      0.0046999000
_diffrn_orient_matrix_UB_31      0.0063298000
_diffrn_orient_matrix_UB_32      0.0133119000
_diffrn_orient_matrix_UB_33      -0.0903929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3577
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.088
_diffrn_reflns_theta_min         5.200
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97506
_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    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 705 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0412P)^2^+0.1241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1755
_reflns_number_total             1799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ma0c01305_si_002.cif
_cod_data_source_block           xl-4-95-2scaled
_cod_database_code               1558461
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H12 O3'
_reflns_odcompleteness_completeness 99.00
_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), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
;
_shelx_res_checksum              83409
_shelx_hkl_checksum              3628
_ins_header
;
TITL XL-4-95-2scaled in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   6.947023   7.510143  17.010516  90.0000  90.0000  90.0000
ZERR    4.00   0.000130   0.000128   0.000306   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H O
UNIT 44.00 48.00 12.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-02-04
_olex2_date_sample_submission    2020-02-03
_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 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.901