# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_jwi-358-2
_database_code_depnum_ccdc_archive 'CCDC 2349053'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2024-04-17 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
;
2H,4H- 2,2-Dimethyl-4-hydroxy-benzo[b]-1,4-oxazin-3-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N O3'
_chemical_formula_sum            'C10 H11 N O3'
_chemical_formula_weight         193.20

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/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9227(7)
_cell_length_b                   5.6720(5)
_cell_length_c                   16.1656(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.498(6)
_cell_angle_gamma                90
_cell_volume                     897.35(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10411
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube, 12x0.4mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            4613
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         28.045
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2133
_reflns_number_gt                1864
_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       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.4259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2133
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_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
O1 O 0.36297(9) 0.23810(16) 0.43491(5) 0.0201(2) Uani 1 1 d . . . . .
C2 C 0.23650(12) 0.1362(2) 0.45205(7) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.15327(12) 0.0371(2) 0.37121(7) 0.0172(2) Uani 1 1 d . . . . .
N4 N 0.15807(10) 0.16631(18) 0.30189(6) 0.0177(2) Uani 1 1 d . . . . .
C4A C 0.24685(12) 0.3604(2) 0.29962(8) 0.0170(2) Uani 1 1 d . . . . .
C5 C 0.23420(12) 0.5154(2) 0.23213(8) 0.0193(3) Uani 1 1 d . . . . .
H5 H 0.1630(16) 0.489(3) 0.1855(9) 0.019(4) Uiso 1 1 d . . . . .
C6 C 0.32538(13) 0.7024(2) 0.23430(8) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.3159(17) 0.811(3) 0.1880(10) 0.025(4) Uiso 1 1 d . . . . .
C7 C 0.42878(13) 0.7332(2) 0.30271(8) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.4921(17) 0.866(3) 0.3033(10) 0.026(4) Uiso 1 1 d . . . . .
C8 C 0.44097(13) 0.5779(2) 0.37027(8) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.5113(17) 0.597(3) 0.4203(10) 0.026(4) Uiso 1 1 d . . . . .
C8A C 0.34920(12) 0.3932(2) 0.36873(7) 0.0178(2) Uani 1 1 d . . . . .
C9 C 0.28036(14) -0.0597(2) 0.51437(8) 0.0219(3) Uani 1 1 d . . . . .
H9A H 0.1983(18) -0.132(3) 0.5331(10) 0.031(3) Uiso 1 1 d . U . . .
H9B H 0.3377(18) 0.008(3) 0.5635(11) 0.031(3) Uiso 1 1 d . U . . .
H9C H 0.3331(18) -0.181(3) 0.4899(10) 0.031(3) Uiso 1 1 d . U . . .
C10 C 0.15055(14) 0.3225(2) 0.48767(8) 0.0229(3) Uani 1 1 d . . . . .
H10A H 0.1292(18) 0.456(3) 0.4482(11) 0.033(3) Uiso 1 1 d . U . . .
H10B H 0.2027(18) 0.378(3) 0.5413(11) 0.033(3) Uiso 1 1 d . U . . .
H10C H 0.0635(19) 0.250(3) 0.4993(11) 0.033(3) Uiso 1 1 d . U . . .
O11 O 0.08203(9) -0.14072(15) 0.37222(5) 0.0216(2) Uani 1 1 d . . . . .
O12 O 0.08603(9) 0.08332(16) 0.22646(5) 0.0204(2) Uani 1 1 d . . . . .
H12 H 0.020(2) 0.197(4) 0.2091(12) 0.046(5) Uiso 1 1 d . . . . .


_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
O1 C8A 1.3744(15) . ?
O1 C2 1.4492(14) . ?
C2 C9 1.5150(17) . ?
C2 C10 1.5288(17) . ?
C2 C3 1.5330(17) . ?
C3 O11 1.2331(15) . ?
C3 N4 1.3465(15) . ?
N4 O12 1.3900(13) . ?
N4 C4A 1.4141(15) . ?
C4A C5 1.3908(17) . ?
C4A C8A 1.3928(17) . ?
C5 C6 1.3909(18) . ?
C5 H5 0.956(16) . ?
C6 C7 1.3899(19) . ?
C6 H6 0.961(17) . ?
C7 C8 1.3930(18) . ?
C7 H7 0.982(17) . ?
C8 C8A 1.3854(17) . ?
C8 H8 0.983(17) . ?
C9 H9A 1.001(18) . ?
C9 H9B 0.975(18) . ?
C9 H9C 0.986(18) . ?
C10 H10A 0.989(18) . ?
C10 H10B 0.985(18) . ?
C10 H10C 1.002(18) . ?
O12 H12 0.93(2) . ?

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
C8A O1 C2 115.22(9) . . ?
O1 C2 C9 104.88(10) . . ?
O1 C2 C10 110.55(10) . . ?
C9 C2 C10 111.92(10) . . ?
O1 C2 C3 110.19(9) . . ?
C9 C2 C3 110.66(10) . . ?
C10 C2 C3 108.61(10) . . ?
O11 C3 N4 123.73(11) . . ?
O11 C3 C2 121.21(11) . . ?
N4 C3 C2 114.93(10) . . ?
C3 N4 O12 117.52(10) . . ?
C3 N4 C4A 123.59(10) . . ?
O12 N4 C4A 118.24(9) . . ?
C5 C4A C8A 120.28(11) . . ?
C5 C4A N4 122.45(11) . . ?
C8A C4A N4 117.27(10) . . ?
C4A C5 C6 119.23(12) . . ?
C4A C5 H5 118.6(9) . . ?
C6 C5 H5 122.2(9) . . ?
C7 C6 C5 120.50(12) . . ?
C7 C6 H6 120.2(10) . . ?
C5 C6 H6 119.3(10) . . ?
C6 C7 C8 120.10(12) . . ?
C6 C7 H7 119.5(9) . . ?
C8 C7 H7 120.4(10) . . ?
C8A C8 C7 119.50(12) . . ?
C8A C8 H8 118.3(10) . . ?
C7 C8 H8 122.2(10) . . ?
O1 C8A C8 119.30(11) . . ?
O1 C8A C4A 120.29(11) . . ?
C8 C8A C4A 120.37(11) . . ?
C2 C9 H9A 109.9(10) . . ?
C2 C9 H9B 108.6(11) . . ?
H9A C9 H9B 108.0(14) . . ?
C2 C9 H9C 111.0(10) . . ?
H9A C9 H9C 110.4(14) . . ?
H9B C9 H9C 108.9(14) . . ?
C2 C10 H10A 111.0(10) . . ?
C2 C10 H10B 107.9(10) . . ?
H10A C10 H10B 110.5(15) . . ?
C2 C10 H10C 109.9(10) . . ?
H10A C10 H10C 109.6(15) . . ?
H10B C10 H10C 108.0(14) . . ?
N4 O12 H12 105.4(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A O1 C2 C9 169.12(10) . . . . ?
C8A O1 C2 C10 -70.07(13) . . . . ?
C8A O1 C2 C3 49.99(13) . . . . ?
O1 C2 C3 O11 146.08(11) . . . . ?
C9 C2 C3 O11 30.54(15) . . . . ?
C10 C2 C3 O11 -92.69(13) . . . . ?
O1 C2 C3 N4 -37.82(14) . . . . ?
C9 C2 C3 N4 -153.36(10) . . . . ?
C10 C2 C3 N4 83.40(12) . . . . ?
O11 C3 N4 O12 -4.88(17) . . . . ?
C2 C3 N4 O12 179.14(9) . . . . ?
O11 C3 N4 C4A -175.44(11) . . . . ?
C2 C3 N4 C4A 8.58(16) . . . . ?
C3 N4 C4A C5 -168.68(11) . . . . ?
O12 N4 C4A C5 20.82(16) . . . . ?
C3 N4 C4A C8A 10.96(17) . . . . ?
O12 N4 C4A C8A -159.53(10) . . . . ?
C8A C4A C5 C6 0.39(18) . . . . ?
N4 C4A C5 C6 -179.98(11) . . . . ?
C4A C5 C6 C7 0.57(18) . . . . ?
C5 C6 C7 C8 -0.70(19) . . . . ?
C6 C7 C8 C8A -0.13(19) . . . . ?
C2 O1 C8A C8 149.08(11) . . . . ?
C2 O1 C8A C4A -33.06(15) . . . . ?
C7 C8 C8A O1 178.94(11) . . . . ?
C7 C8 C8A C4A 1.09(18) . . . . ?
C5 C4A C8A O1 -179.06(11) . . . . ?
N4 C4A C8A O1 1.29(16) . . . . ?
C5 C4A C8A C8 -1.23(18) . . . . ?
N4 C4A C8A C8 179.12(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 O11 0.956(16) 2.564(16) 3.4248(16) 149.9(12) 2 yes
O12 H12 O11 0.93(2) 1.78(2) 2.6263(13) 150.4(17) 2 yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.043





