# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Moni_Benzoxazine_hydroxyle
_database_code_depnum_ccdc_archive 'CCDC 2161734'
loop_
_audit_author_name
_audit_author_address
'Monique Tillard'
;ICGM CNRS Montpellier
France
;
_audit_update_record             
;
2022-03-24 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
#=================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
4-(3-(furan-2-ylmethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazin-2-yl)phenol
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C19 H17 N O3'
_exptl_crystal_recrystallization_method 'cyclohexane, ethyl acetate '
_chemical_melting_point          421

_exptl_crystal_description       platelet
_exptl_crystal_colour            pale-orange

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         307.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   8.9115(6)
_cell_length_b                   18.9555(13)
_cell_length_c                   9.6086(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.430(3)
_cell_angle_gamma                90
_cell_volume                     1571.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4804
_cell_measurement_theta_min      2.4382
_cell_measurement_theta_max      30.4478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'ImuS microfocus'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayer optic'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            25779
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3793
_reflns_number_gt                3264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.12'
_computing_cell_refinement       'APEX3 v2017.3-0 Bruker Nonius AXS,2017)'
_computing_data_reduction        'APEX3 v2017.3-0 Bruker Nonius AXS,2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'DIAMOND, K. Brandenburg 2010'
_computing_publication_material  ?

_refine_special_details          
;
The mismeasured reflections (-1 3 1), (0 4 1) and (-2 0 2) due to the beam stop 
have been omitted from the final refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0503P)²+0.4358P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0051(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 . ?

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


# D H A D-H H...A D...A D-H...A 
# - - - --- ----- ----- ------- 
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)

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-2

