Synthesis, characterization, and cure chemistry of renewable bis(cyanate) esters derived from 2-methoxy-4-methylphenol.
Meylemans, Heather A.; Harvey, Benjamin G.; Reams, Josiah T.; Guenthner, Andrew J.; Cambrea, Lee R.; Groshens, Thomas J.; Baldwin, Lawrence C.; Garrison, Michael D.; Mabry, Joseph M.; Biomacromolecules 14 (2013) 771–780; doi:10.1021/bm3018438

data_1511777
_publ_section_title
;
 Synthesis, characterization, and cure chemistry of renewable bis(cyanate)
 esters derived from 2-methoxy-4-methylphenol.
;
_journal_issue                   3
_journal_name_full               Biomacromolecules
_journal_page_first              771
_journal_page_last               780
_journal_paper_doi               10.1021/bm3018438
_journal_volume                  14
_journal_year                    2013
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_chemical_melting_point          360.5(5)
_chemical_name_systematic
;
5,5?-(ethane-1,1-diyl)bis(1-cyanato-
2-methoxy-4-methylbenzene)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                106.625(4)
_cell_angle_beta                 95.476(4)
_cell_angle_gamma                105.337(4)
_cell_formula_units_Z            2
_cell_length_a                   7.062(2)
_cell_length_b                   11.734(4)
_cell_length_c                   12.337(4)
_cell_measurement_reflns_used    947
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      30.0792
_cell_measurement_theta_min      1.7560
_cell_volume                     928.4(5)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       'profile data from Omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10119
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.128
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.2459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2291
_reflns_number_total             3281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm3018438_si_002.cif
_cod_data_source_block           Compound_3
_cod_database_code               1511777