The mechanochemical synthesis of environmentally benign fully biobased 4th generation benzoxazines and their polymers: mechanistic insights into the catalytic activity of latent catalysts
Duhan, Vaishaly; Yadav, Shivani; Len, Christophe; Lochab, Bimlesh; Green Chemistry 26 (2024) 483–497; doi:10.1039/D3GC03522K

data_7247850
_publ_section_title
;
 The mechanochemical synthesis of environmentally benign fully biobased
 4th generation benzoxazines and their polymers: mechanistic insights into
 the catalytic activity of latent catalysts
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              483
_journal_page_last               497
_journal_paper_doi               10.1039/D3GC03522K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C21 H21 N O5'
_chemical_formula_sum            'C21 H21 N O5'
_chemical_formula_weight         367.405
_chemical_name_systematic        1,3-benozoxazine
_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_Int_Tables_number      2
_audit_creation_date             2023-09-28
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-28 deposited with the CCDC.	2023-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                71.148(3)
_cell_angle_beta                 82.961(3)
_cell_angle_gamma                81.232(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9414(6)
_cell_length_b                   9.2292(7)
_cell_length_c                   13.4539(11)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    289(2)
_cell_measurement_theta_max      31.47
_cell_measurement_theta_min      2.40
_cell_volume                     919.44(13)
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      289.27
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.9864
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.9880
_diffrn_reflns_Laue_measured_fraction_max 0.9864
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16262
_diffrn_reflns_point_group_measured_fraction_full 0.9880
_diffrn_reflns_point_group_measured_fraction_max 0.9864
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.40
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            'pale white'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             388.273
_refine_diff_density_max         0.1830
_refine_diff_density_min         -0.1980
_refine_diff_density_rms         0.0367
_refine_ls_d_res_high            0.7994
_refine_ls_d_res_low             8.4919
_refine_ls_extinction_coef       0.093(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0890
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0890
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.1954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2908
_reflns_number_total             3710
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3gc03522k2.cif
_cod_data_source_block           mo_VD119BNZX_0m_a
_cod_depositor_comments
'Adding full bibliography for 7247850--7247852.cif.'
_cod_database_code               7247850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C18(H18), C11(H11), C4(H4a), C12(H12), C13(H13), C2(H2),
 C3(H3)
2.d Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C00R(H00a,H00b,H00c)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'