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_1511778
_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         'C19 H18 N2 O4'
_chemical_formula_sum            'C19 H18 N2 O4'
_chemical_formula_weight         338.35
_chemical_melting_point          396(1)
_chemical_name_systematic
;
bis(5-cyanato-4-methoxy-
2-methylphenyl)methane
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 112.4460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5687(12)
_cell_length_b                   4.7770(3)
_cell_length_c                   22.8294(16)
_cell_measurement_reflns_used    899
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      26.5088
_cell_measurement_theta_min      1.9204
_cell_volume                     1770.8(2)
_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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9088
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.93
_diffrn_source_type              'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.109
_refine_ls_extinction_coef       0.0023(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0420P)^2^+0.8982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                953
_reflns_number_total             1563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bm3018438_si_002.cif
_cod_data_source_block           Compound_2
_cod_database_code               1511778