# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2234739'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
#data_oko1

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1-hydroxy-2-methyl-1H-quinazolin-4-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N2 O2'
_chemical_formula_sum            'C9 H8 N2 O2'
_chemical_formula_weight         176.17

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'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1643(7)
_cell_length_b                   9.1814(7)
_cell_length_c                   10.4783(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.381(6)
_cell_angle_gamma                90
_cell_volume                     796.56(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3502
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.987
_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, 12 x 0.4 mm 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            4012
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.091
_diffrn_reflns_theta_max         27.845
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1883
_reflns_number_gt                1370
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0698P)²+1.0819P] 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         1883
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1769
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
N1 N 0.6355(2) 0.3556(2) 0.0840(2) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.7420(3) 0.4624(3) 0.1466(3) 0.0185(5) Uani 1 1 d . . . . .
N3 N 0.7364(2) 0.5456(2) 0.2471(2) 0.0189(5) Uani 1 1 d . . . . .
C4 C 0.6195(3) 0.5219(3) 0.2941(3) 0.0173(5) Uani 1 1 d . . . . .
C5 C 0.5038(3) 0.4046(3) 0.2319(3) 0.0168(5) Uani 1 1 d . . . . .
C6 C 0.3856(3) 0.3700(3) 0.2796(3) 0.0189(5) Uani 1 1 d . . . . .
H6 H 0.384(3) 0.425(3) 0.356(3) 0.007(6) Uiso 1 1 d . . . . .
C7 C 0.2763(3) 0.2600(3) 0.2150(3) 0.0210(6) Uani 1 1 d . . . . .
H7 H 0.196(4) 0.236(3) 0.249(3) 0.019(7) Uiso 1 1 d . . . . .
C8 C 0.2823(3) 0.1838(3) 0.1016(3) 0.0223(6) Uani 1 1 d . . . . .
H8 H 0.206(4) 0.106(4) 0.058(3) 0.029(8) Uiso 1 1 d . . . . .
C9 C 0.3997(3) 0.2111(3) 0.0554(3) 0.0200(5) Uani 1 1 d . . . . .
H9 H 0.402(4) 0.157(4) -0.022(3) 0.025(8) Uiso 1 1 d . . . . .
C10 C 0.5117(3) 0.3224(3) 0.1223(3) 0.0162(5) Uani 1 1 d . . . . .
O11 O 0.6158(2) 0.59989(19) 0.39133(19) 0.0204(4) Uani 1 1 d . . . . .
C12 C 0.8732(3) 0.4864(3) 0.0994(3) 0.0231(6) Uani 1 1 d . . . . .
H12A H 0.943(4) 0.404(4) 0.123(3) 0.025(4) Uiso 1 1 d . U . . .
H12B H 0.930(4) 0.575(4) 0.145(3) 0.025(4) Uiso 1 1 d . U . . .
H12C H 0.828(4) 0.494(3) -0.004(4) 0.025(4) Uiso 1 1 d . U . . .
O13 O 0.6483(2) 0.2729(2) -0.02127(19) 0.0203(4) Uani 1 1 d . . . . .
H13 H 0.737(6) 0.207(5) 0.033(5) 0.069(14) 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
N1 C2 1.340(3) . ?
N1 O13 1.384(3) . ?
N1 C10 1.390(3) . ?
C2 N3 1.320(3) . ?
C2 C12 1.500(3) . ?
N3 C4 1.374(3) . ?
C4 O11 1.258(3) . ?
C4 C5 1.455(3) . ?
C5 C10 1.402(3) . ?
C5 C6 1.410(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.95(3) . ?
C7 C8 1.401(4) . ?
C7 H7 0.97(3) . ?
C8 C9 1.379(4) . ?
C8 H8 0.97(3) . ?
C9 C10 1.405(4) . ?
C9 H9 0.96(3) . ?
C12 H12A 0.95(3) . ?
C12 H12B 0.97(3) . ?
C12 H12C 0.98(3) . ?
O13 H13 0.97(5) . ?

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
C2 N1 O13 119.9(2) . . ?
C2 N1 C10 122.1(2) . . ?
O13 N1 C10 117.9(2) . . ?
N3 C2 N1 123.0(2) . . ?
N3 C2 C12 119.3(2) . . ?
N1 C2 C12 117.7(2) . . ?
C2 N3 C4 119.8(2) . . ?
O11 C4 N3 119.7(2) . . ?
O11 C4 C5 121.1(2) . . ?
N3 C4 C5 119.2(2) . . ?
C10 C5 C6 119.1(2) . . ?
C10 C5 C4 118.8(2) . . ?
C6 C5 C4 122.1(2) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 121.9(16) . . ?
C5 C6 H6 118.1(16) . . ?
C6 C7 C8 119.9(2) . . ?
C6 C7 H7 119.5(18) . . ?
C8 C7 H7 120.6(18) . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 H8 119.2(19) . . ?
C7 C8 H8 118.9(19) . . ?
C8 C9 C10 118.1(2) . . ?
C8 C9 H9 120.4(19) . . ?
C10 C9 H9 121.5(19) . . ?
N1 C10 C5 117.0(2) . . ?
N1 C10 C9 121.9(2) . . ?
C5 C10 C9 121.1(2) . . ?
C2 C12 H12A 109.7(19) . . ?
C2 C12 H12B 106.9(18) . . ?
H12A C12 H12B 113(3) . . ?
C2 C12 H12C 110.7(19) . . ?
H12A C12 H12C 105(3) . . ?
H12B C12 H12C 112(3) . . ?
N1 O13 H13 102(3) . . ?

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
O13 N1 C2 N3 179.7(2) . . . . ?
C10 N1 C2 N3 -1.2(4) . . . . ?
O13 N1 C2 C12 -0.5(3) . . . . ?
C10 N1 C2 C12 178.5(2) . . . . ?
N1 C2 N3 C4 1.6(4) . . . . ?
C12 C2 N3 C4 -178.2(2) . . . . ?
C2 N3 C4 O11 178.9(2) . . . . ?
C2 N3 C4 C5 0.1(3) . . . . ?
O11 C4 C5 C10 179.1(2) . . . . ?
N3 C4 C5 C10 -2.2(3) . . . . ?
O11 C4 C5 C6 -1.8(4) . . . . ?
N3 C4 C5 C6 177.0(2) . . . . ?
C10 C5 C6 C7 -2.4(4) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 2.9(4) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C2 N1 C10 C5 -0.9(3) . . . . ?
O13 N1 C10 C5 178.2(2) . . . . ?
C2 N1 C10 C9 179.5(2) . . . . ?
O13 N1 C10 C9 -1.4(3) . . . . ?
C6 C5 C10 N1 -176.7(2) . . . . ?
C4 C5 C10 N1 2.5(3) . . . . ?
C6 C5 C10 C9 2.9(4) . . . . ?
C4 C5 C10 C9 -177.9(2) . . . . ?
C8 C9 C10 N1 179.0(2) . . . . ?
C8 C9 C10 C5 -0.6(4) . . . . ?

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
O13 H13 O11 0.97(5) 1.58(5) 2.555(3) 175(4) 2_645 yes

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.082

