#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:55:09 +0200 (Mon, 07 Nov 2022) $
#$Revision: 279028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567671.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567671
loop_
_publ_author_name
'Tavernier, Romain'
'Granado, Lérys'
'Tillard, Monique'
'Van Renterghem, Louis'
'Métro, Thomas-Xavier'
'Lamaty, Frédéric'
'Bonnaud, Leïla'
'Raquez, Jean-Marie'
'David, Ghislain'
'Caillol, Sylvain'
_publ_section_title
;
 Solvent-free synthesis of a formaldehyde-free benzoxazine monomer: study
 of its curing acceleration effect for commercial benzoxazine
;
_journal_issue                   40
_journal_name_full               'Polymer Chemistry'
_journal_page_first              5745
_journal_page_last               5756
_journal_paper_doi               10.1039/D2PY00462C
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_chemical_melting_point          421
_chemical_name_systematic
4-(3-(furan-2-ylmethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-yl)phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-03-24 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.430(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9115(6)
_cell_length_b                   18.9555(13)
_cell_length_c                   9.6086(8)
_cell_measurement_reflns_used    4804
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.4478
_cell_measurement_theta_min      2.4382
_cell_volume                     1571.9(2)
_computing_cell_refinement       'APEX3 v2017.3-0 Bruker Nonius AXS,2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.12'
_computing_data_reduction        'APEX3 v2017.3-0 Bruker Nonius AXS,2017)'
_computing_molecular_graphics    'DIAMOND, K. Brandenburg 2010'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayer optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25779
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.438
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'ImuS microfocus'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            pale-orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       platelet
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method 'cyclohexane, ethyl acetate '
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0051(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0503P)²+0.4358P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             3793
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00462c2.cif
_cod_data_source_block           Moni_Benzoxazine_hydroxyle
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567671.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1567671
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.35186(10) 0.58039(5) 0.21406(9) 0.0249(2) Uani 1 1 d . . . . .
C4 C 0.22411(15) 0.35170(7) -0.05344(18) 0.0454(3) Uani 1 1 d . . . . .
H4 H 0.1816 0.3166 -0.1226 0.054 Uiso 1 1 calc R U . . .
C5 C 0.29939(15) 0.33182(7) 0.08524(18) 0.0463(3) Uani 1 1 d . . . . .
H5 H 0.3071 0.2833 0.1112 0.056 Uiso 1 1 calc R U . . .
C7 C 0.35336(12) 0.45413(6) 0.14945(13) 0.0295(2) Uani 1 1 d . . . . .
C8 C 0.42588(12) 0.51095(6) 0.25446(12) 0.0287(2) Uani 1 1 d . . . . .
H8A H 0.4161 0.4980 0.3516 0.034 Uiso 1 1 calc R U . . .
H8B H 0.5376 0.5144 0.2580 0.034 Uiso 1 1 calc R U . . .
C9 C 0.19584(12) 0.58277(6) 0.24269(12) 0.0291(2) Uani 1 1 d . . . . .
H9A H 0.1383 0.6239 0.1924 0.035 Uiso 1 1 calc R U . . .
H9B H 0.1379 0.5396 0.2035 0.035 Uiso 1 1 calc R U . . .
C10 C 0.20376(12) 0.58804(6) 0.39816(12) 0.0272(2) Uani 1 1 d . . . . .
C11 C 0.23890(16) 0.64540(7) 0.60162(14) 0.0422(3) Uani 1 1 d . . . . .
H11 H 0.2611 0.6822 0.6708 0.051 Uiso 1 1 calc R U . . .
C12 C 0.20000(17) 0.58042(8) 0.62834(14) 0.0433(3) Uani 1 1 d . . . . .
H12 H 0.1892 0.5625 0.7176 0.052 Uiso 1 1 calc R U . . .
C13 C 0.17744(17) 0.54262(7) 0.49621(14) 0.0398(3) Uani 1 1 d . . . . .
H13 H 0.1491 0.4944 0.4808 0.048 Uiso 1 1 calc R U . . .
C14 C 0.28296(12) 0.66567(6) 0.01273(11) 0.0265(2) Uani 1 1 d . . . . .
C15 C 0.12835(12) 0.67718(6) -0.05865(12) 0.0286(2) Uani 1 1 d . . . . .
H15 H 0.0596 0.6382 -0.0819 0.034 Uiso 1 1 calc R U . . .
C16 C 0.07374(13) 0.74482(6) -0.09602(12) 0.0309(2) Uani 1 1 d . . . . .
H16 H -0.0321 0.7520 -0.1437 0.037 Uiso 1 1 calc R U . . .
C17 C 0.17327(14) 0.80207(6) -0.06396(13) 0.0334(3) Uani 1 1 d . . . . .
C18 C 0.32854(14) 0.79129(7) 0.00563(15) 0.0391(3) Uani 1 1 d . . . . .
H18 H 0.3976 0.8302 0.0273 0.047 Uiso 1 1 calc R U . . .
C19 C 0.38147(13) 0.72355(6) 0.04301(13) 0.0335(3) Uani 1 1 d . . . . .
H19 H 0.4874 0.7165 0.0904 0.040 Uiso 1 1 calc R U . . .
C6 C 0.36329(14) 0.38270(6) 0.18569(16) 0.0383(3) Uani 1 1 d . . . . .
H6 H 0.4146 0.3688 0.2806 0.046 Uiso 1 1 calc R U . . .
O1 O 0.25103(9) 0.54238(4) -0.03141(8) 0.03187(19) Uani 1 1 d . . . . .
C1 C 0.34585(12) 0.59361(6) 0.06288(11) 0.0265(2) Uani 1 1 d . . . . .
H1 H 0.4537 0.5903 0.0503 0.032 Uiso 1 1 calc R U . . .
O2 O 0.24289(11) 0.65245(4) 0.46093(10) 0.0403(2) Uani 1 1 d . . . . .
C2 C 0.27417(12) 0.47307(6) 0.01046(13) 0.0294(2) Uani 1 1 d . . . . .
O3 O 0.12658(11) 0.86977(5) -0.09732(12) 0.0465(3) Uani 1 1 d . . . . .
H1O H 0.031(2) 0.8698(10) -0.151(2) 0.070 Uiso 1 1 d . U . . .
C3 C 0.21033(14) 0.42215(7) -0.09194(15) 0.0371(3) Uani 1 1 d . . . . .
H3 H 0.1581 0.4357 -0.1869 0.045 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C8 108.46(8) . . ?
C1 N C9 112.02(8) . . ?
C8 N C9 110.82(8) . . ?
C3 C4 C5 120.60(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.85(12) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C2 C7 C6 118.34(11) . . ?
C2 C7 C8 119.21(10) . . ?
C6 C7 C8 122.45(11) . . ?
N C8 C7 111.79(9) . . ?
N C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 N 112.19(9) . . ?
C10 C9 H9A 109.2 . . ?
N C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
N C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C13 C10 O2 109.49(10) . . ?
C13 C10 C9 133.90(11) . . ?
O2 C10 C9 116.59(9) . . ?
C12 C11 O2 110.83(11) . . ?
C12 C11 H11 124.6 . . ?
O2 C11 H11 124.6 . . ?
C11 C12 C13 106.29(11) . . ?
C11 C12 H12 126.9 . . ?
C13 C12 H12 126.9 . . ?
C10 C13 C12 106.99(12) . . ?
C10 C13 H13 126.5 . . ?
C12 C13 H13 126.5 . . ?
C19 C14 C15 118.33(10) . . ?
C19 C14 C1 118.86(9) . . ?
C15 C14 C1 122.77(10) . . ?
C16 C15 C14 120.79(10) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.15(10) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
O3 C17 C16 122.95(10) . . ?
O3 C17 C18 117.36(11) . . ?
C16 C17 C18 119.69(11) . . ?
C19 C18 C17 119.60(11) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C14 121.42(10) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C5 C6 C7 120.88(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 O1 C1 115.88(8) . . ?
O1 C1 N 112.20(9) . . ?
O1 C1 C14 107.15(8) . . ?
N C1 C14 113.03(8) . . ?
O1 C1 H1 108.1 . . ?
N C1 H1 108.1 . . ?
C14 C1 H1 108.1 . . ?
C11 O2 C10 106.39(9) . . ?
O1 C2 C7 122.02(10) . . ?
O1 C2 C3 116.75(11) . . ?
C7 C2 C3 121.21(11) . . ?
C17 O3 H1O 109.5(13) . . ?
C4 C3 C2 119.10(13) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
loop_
_geom_bond_atom_site_label_D
_geom_bond_atom_site_label_H
_geom_contact_atom_site_label_a
_geom_bond_distance_DH
_geom_contact_distance_HA
_geom_contact_distance_DA
_geom_angle_DHA
c12 H12 O1 0.950 2.364(1) 3.265(2) 158.08(8)
O3 H1O N 0.878 2.02(2) 2.822(1) 150.9(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N C1 1.4619(13) . ?
N C8 1.4800(13) . ?
N C9 1.4837(14) . ?
C4 C3 1.3830(19) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3828(19) . ?
C5 H5 0.9500 . ?
C7 C2 1.3932(16) . ?
C7 C6 1.3954(16) . ?
C7 C8 1.5069(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.4812(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.3394(16) . ?
C10 O2 1.3679(13) . ?
C11 C12 1.322(2) . ?
C11 O2 1.3677(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.4279(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3898(16) . ?
C14 C15 1.3947(15) . ?
C14 C1 1.5091(14) . ?
C15 C16 1.3866(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3868(16) . ?
C16 H16 0.9500 . ?
C17 O3 1.3625(14) . ?
C17 C18 1.3936(17) . ?
C18 C19 1.3842(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C6 H6 0.9500 . ?
O1 C2 1.3744(14) . ?
O1 C1 1.4479(13) . ?
C1 H1 1.0000 . ?
C2 C3 1.3945(16) . ?
O3 H1O 0.88(2) . ?
C3 H3 0.9500 . ?
