# Supplementary Information (SI) for RSC Advances.
# 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_ea-20000
_database_code_depnum_ccdc_archive 'CCDC 2361411'
loop_
_audit_author_name
_audit_author_address
'Gerardo Aguirre'
;Tecnologico Nacional de Mexico CGIQ ITT
Mexico
;
_audit_update_record             
;
2024-06-09 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2021-05-28
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
3-(4-chlorophenyl)-5-(p-tolyl)-6H-1,2-oxazin-6-one
_chemical_formula_moiety         'C17 H12 Cl N O2'
_chemical_formula_sum            'C17 H12 Cl N O2'
_chemical_formula_weight         297.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.54533(13)
_cell_length_b                   29.5464(5)
_cell_length_c                   7.4552(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.691(2)
_cell_angle_gamma                90
_cell_volume                     1411.85(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5942
_cell_measurement_temperature    294.1(4)
_cell_measurement_theta_max      70.5110
_cell_measurement_theta_min      3.0020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent intense colourless'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.770
_diffrn_reflns_theta_min         2.991
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.1(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1970
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  42.00   1.00    2.84    --    0.00  77.00  30.00   86
  2  ω      6.00  51.00   1.00    2.84    --    0.00 -99.00-120.00   45
  3  ω   -155.00 -82.00   1.00   11.36    --  -54.67 -77.00-180.00   73
  4  ω   -149.00 -82.00   1.00   11.36    --  -54.67 -99.00 -90.00   67
  5  ω    -86.00  -6.00   1.00   11.36    --  -54.67 125.00 120.00   80
  6  ω    103.00 155.00   1.00   11.36    --   54.67  77.00-120.00   52
  7  ω    103.00 155.00   1.00   11.36    --   54.67  77.00   0.00   52
  8  ω     97.00 146.00   1.00   11.36    --   54.67 125.00  30.00   49
  9  ω     18.00 109.00   1.00   11.36    --  109.35-111.00  60.00   91
 10  ω     61.00 146.00   1.00   11.36    --  109.35 178.00 -90.00   85
 11  ω    103.00 178.00   1.00   11.36    --  109.35  77.00 -90.00   75
 12  ω    104.00 178.00   1.00   11.36    --  109.35 111.00  30.00   74
 13  ω    103.00 178.00   1.00   11.36    --  109.35  77.00 -60.00   75
 14  ω    104.00 178.00   1.00   11.36    --  109.35 111.00 150.00   74
 15  ω     61.00 146.00   1.00   11.36    --  109.35 178.00   0.00   85
 16  ω    104.00 178.00   1.00   11.36    --  109.35 111.00   0.00   74
 17  ω     65.00 178.00   1.00   11.36    --  109.35  64.00  60.00  113
 18  ω    -21.00  44.00   1.00    2.84    --    0.00 -77.00-180.00   65
 19  ω    -21.00  44.00   1.00    2.84    --    0.00 -77.00  60.00   65
 20  ω   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00-150.00  134
 21  ω   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00 120.00  134
 22  ω   -147.00 -13.00   1.00   11.36    --  -54.67 -57.00  30.00  134
 23  ω     13.00 147.00   1.00   11.36    --   54.67  57.00  30.00  134
 24  ω     27.00 112.00   1.00   11.36    --   54.67-125.00  30.00   85
 25  ω      8.00 145.00   1.00   11.36    --   54.67  38.00 -30.00  137
 26  ω     68.00 178.00   1.00   11.36    --  109.35  50.00-180.00  110
 27  ω    104.00 178.00   1.00   11.36    --  109.35 111.00  90.00   74
 28  ω     65.00 178.00   1.00   11.36    --  109.35  64.00-120.00  113
 29  ω     68.00 178.00   1.00   11.36    --  109.35  50.00   0.00  110
 30  ω     65.00 178.00   1.00   11.36    --  109.35  64.00 120.00  113
 31  ω     65.00 178.00   1.00   11.36    --  109.35  64.00 -60.00  113
 32  ω     65.00  99.00   1.00   11.36    --  109.35  64.00  90.00   34
 33  ω     65.00 178.00   1.00   11.36    --  109.35  64.00-150.00  113
 34  ω     13.00 106.00   1.00   11.36    --  109.35 -92.00  90.00   93
 35  ω     65.00 178.00   1.00   11.36    --  109.35  64.00  30.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1284231000
_diffrn_orient_matrix_UB_12      0.0433272000
_diffrn_orient_matrix_UB_13      0.0089913000
_diffrn_orient_matrix_UB_21      0.2031406000
_diffrn_orient_matrix_UB_22      0.0274882000
_diffrn_orient_matrix_UB_23      0.0542996000
_diffrn_orient_matrix_UB_31      -0.0020233000
_diffrn_orient_matrix_UB_32      0.0092554000
_diffrn_orient_matrix_UB_33      -0.2037458000
_diffrn_oxdiff_digest_frames     
;
01ca637be32266ce0a4c8804dec1f64cda00031f571
;
_diffrn_oxdiff_digest_hkl        
;
01df3ceeae55fd2ff27d6132b31034a6947767
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2204
_reflns_number_total             2676
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.3478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C 0.8957(3) 0.24373(7) 1.1515(3) 0.0558(5) Uani 1 1 d . . . . .
C2 C 0.6865(3) 0.25409(6) 1.0457(2) 0.0471(4) Uani 1 1 d . . . . .
C3 C 0.5665(3) 0.21818(6) 0.9807(3) 0.0489(4) Uani 1 1 d . . . . .
H3 H 0.431893 0.223186 0.914747 0.059 Uiso 1 1 calc R . . . .
C4 C 0.6403(3) 0.17261(6) 1.0103(3) 0.0490(4) Uani 1 1 d . . . . .
C5 C 0.5045(3) 0.13308(6) 0.9471(2) 0.0491(4) Uani 1 1 d . . . . .
C6 C 0.2905(3) 0.13729(7) 0.9065(3) 0.0610(5) Uani 1 1 d . . . . .
H6 H 0.229952 0.165339 0.917939 0.073 Uiso 1 1 calc R . . . .
C7 C 0.1647(3) 0.10044(7) 0.8490(3) 0.0679(6) Uani 1 1 d . . . . .
H7 H 0.020325 0.103634 0.822001 0.081 Uiso 1 1 calc R . . . .
C8 C 0.2536(4) 0.05919(7) 0.8319(3) 0.0643(6) Uani 1 1 d . . . . .
C9 C 0.4660(4) 0.05384(7) 0.8729(3) 0.0678(6) Uani 1 1 d . . . . .
H9 H 0.525123 0.025626 0.861721 0.081 Uiso 1 1 calc R . . . .
C10 C 0.5906(3) 0.09059(7) 0.9305(3) 0.0626(5) Uani 1 1 d . . . . .
H10 H 0.734715 0.087023 0.958943 0.075 Uiso 1 1 calc R . . . .
C11 C 0.6179(3) 0.30145(6) 1.0131(3) 0.0485(4) Uani 1 1 d . . . . .
C12 C 0.4062(3) 0.31180(7) 0.9649(3) 0.0601(5) Uani 1 1 d . . . . .
H12 H 0.308564 0.288793 0.961687 0.072 Uiso 1 1 calc R . . . .
C13 C 0.3385(3) 0.35524(7) 0.9219(3) 0.0641(5) Uani 1 1 d . . . . .
H13 H 0.195966 0.360975 0.890621 0.077 Uiso 1 1 calc R . . . .
C14 C 0.4774(3) 0.39061(7) 0.9242(3) 0.0588(5) Uani 1 1 d . . . . .
C15 C 0.6864(4) 0.38051(7) 0.9737(3) 0.0687(6) Uani 1 1 d . . . . .
H15 H 0.783295 0.403699 0.977561 0.082 Uiso 1 1 calc R . . . .
C16 C 0.7572(3) 0.33717(7) 1.0179(3) 0.0625(5) Uani 1 1 d . . . . .
H16 H 0.899809 0.331765 1.051277 0.075 Uiso 1 1 calc R . . . .
C17 C 0.3995(4) 0.43822(7) 0.8730(3) 0.0758(7) Uani 1 1 d . . . . .
H17A H 0.336710 0.439241 0.744955 0.114 Uiso 1 1 calc GR . . . .
H17B H 0.514594 0.458985 0.897870 0.114 Uiso 1 1 calc GR . . . .
H17C H 0.298023 0.446534 0.943684 0.114 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.09423(12) 0.01271(2) 0.75943(11) 0.1009(3) Uani 1 1 d . . . . .
N1 N 0.8290(3) 0.16260(6) 1.0906(3) 0.0633(5) Uani 1 1 d . . . . .
O1 O 1.0219(2) 0.26951(5) 1.2355(2) 0.0793(5) Uani 1 1 d . . . . .
O2 O 0.9585(2) 0.19950(5) 1.1571(2) 0.0671(4) Uani 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
C1 C2 1.468(2) . ?
C1 O1 1.202(2) . ?
C1 O2 1.368(2) . ?
C2 C3 1.350(2) . ?
C2 C11 1.475(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.432(2) . ?
C4 C5 1.485(2) . ?
C4 N1 1.293(2) . ?
C5 C6 1.378(3) . ?
C5 C10 1.392(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(3) . ?
C8 C9 1.371(3) . ?
C8 Cl1 1.743(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(3) . ?
C11 C16 1.390(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 C15 1.376(3) . ?
C14 C17 1.518(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 O2 1.408(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
O1 C1 C2 127.99(19) . . ?
O1 C1 O2 114.78(17) . . ?
O2 C1 C2 117.22(16) . . ?
C1 C2 C11 120.43(16) . . ?
C3 C2 C1 116.12(16) . . ?
C3 C2 C11 123.44(16) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.02(16) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 121.95(15) . . ?
N1 C4 C3 123.15(17) . . ?
N1 C4 C5 114.90(16) . . ?
C6 C5 C4 121.02(17) . . ?
C6 C5 C10 118.28(18) . . ?
C10 C5 C4 120.69(17) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.89(19) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 120.89(19) . . ?
C7 C8 Cl1 119.46(18) . . ?
C9 C8 Cl1 119.64(17) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.33(19) . . ?
C10 C9 H9 120.3 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C2 120.31(16) . . ?
C16 C11 C2 122.67(17) . . ?
C16 C11 C12 116.92(17) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.48(19) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C17 120.7(2) . . ?
C15 C14 C13 117.05(19) . . ?
C15 C14 C17 122.2(2) . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.22(19) . . ?
C16 C15 H15 118.9 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.81(19) . . ?
C15 C16 H16 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 N1 O2 115.86(16) . . ?
C1 O2 N1 124.99(14) . . ?

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
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C11 C12 -160.08(19) . . . . ?
C1 C2 C11 C16 23.8(3) . . . . ?
C2 C1 O2 N1 -9.0(3) . . . . ?
C2 C3 C4 C5 176.77(18) . . . . ?
C2 C3 C4 N1 -4.3(3) . . . . ?
C2 C11 C12 C13 -175.6(2) . . . . ?
C2 C11 C16 C15 175.3(2) . . . . ?
C3 C2 C11 C12 20.7(3) . . . . ?
C3 C2 C11 C16 -155.5(2) . . . . ?
C3 C4 C5 C6 -19.1(3) . . . . ?
C3 C4 C5 C10 162.02(19) . . . . ?
C3 C4 N1 O2 3.1(3) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C4 C5 C10 C9 179.8(2) . . . . ?
C4 N1 O2 C1 3.8(3) . . . . ?
C5 C4 N1 O2 -177.94(16) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C6 C7 C8 Cl1 179.94(18) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C5 -0.3(4) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C11 C2 C3 C4 178.13(18) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C12 C13 C14 C17 178.9(2) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
C17 C14 C15 C16 -179.1(2) . . . . ?
Cl1 C8 C9 C10 -179.76(18) . . . . ?
N1 C4 C5 C6 161.9(2) . . . . ?
N1 C4 C5 C10 -17.0(3) . . . . ?
O1 C1 C2 C3 -172.9(2) . . . . ?
O1 C1 C2 C11 7.8(3) . . . . ?
O1 C1 O2 N1 171.1(2) . . . . ?
O2 C1 C2 C3 7.2(3) . . . . ?
O2 C1 C2 C11 -172.08(18) . . . . ?

_olex2_date_sample_data_collection 2021-05-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.350
_oxdiff_exptl_absorpt_empirical_full_min 0.421
####################################################################### 
# 
# 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_oxa-7_auto
_database_code_depnum_ccdc_archive 'CCDC 2361412'
loop_
_audit_author_name
_audit_author_address
'Gerardo Aguirre'
;Tecnologico Nacional de Mexico CGIQ ITT
Mexico
;
_audit_update_record             
;
2024-06-09 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_audit_creation_date             2024-04-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-(4-methoxyphenyl)-5-(p-tolyl)-6H-1,2-oxazin-6-one
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H15NO2
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.0224(7)
_cell_length_b                   13.540(2)
_cell_length_c                   21.561(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1466.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0560
_cell_measurement_theta_min      4.1780
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent pale orange'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.112
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9792
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.489
_diffrn_reflns_theta_min         3.554
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1970
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  70.00   1.00   29.55    --  -10.19  19.00  30.00  121
  2  ω    -13.00  85.00   1.00   29.55    --   11.05  38.00-120.00   98
  3  ω    -15.00  10.00   1.00   29.55    --   11.05 -99.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338302000
_diffrn_orient_matrix_UB_12      0.0285239000
_diffrn_orient_matrix_UB_13      0.0264006000
_diffrn_orient_matrix_UB_21      -0.0379443000
_diffrn_orient_matrix_UB_22      -0.0435717000
_diffrn_orient_matrix_UB_23      0.0158569000
_diffrn_orient_matrix_UB_31      0.1318565000
_diffrn_orient_matrix_UB_32      -0.0052004000
_diffrn_orient_matrix_UB_33      0.0115976000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             3460
_reflns_odcompleteness_completeness 96.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-ac4 (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.3908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1471
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.5716(4) 1.19853(13) 0.25060(8) 0.0808(6) Uani 1 1 d . . . . .
O2 O 0.8736(3) 1.16126(11) 0.18269(8) 0.0745(5) Uani 1 1 d . . . . .
O3 O 1.8215(3) 0.76619(12) 0.05354(7) 0.0639(5) Uani 1 1 d . . . . .
N1 N 1.0609(4) 1.09914(14) 0.15379(10) 0.0662(6) Uani 1 1 d . . . . .
C1 C 1.0896(4) 1.01216(16) 0.17736(9) 0.0453(5) Uani 1 1 d . . . . .
C2 C 0.9351(4) 0.97804(16) 0.22908(9) 0.0449(5) Uani 1 1 d . . . . .
H2 H 0.963669 0.914562 0.244148 0.054 Uiso 1 1 calc R U . . .
C3 C 0.7509(4) 1.03500(15) 0.25627(9) 0.0427(5) Uani 1 1 d . . . . .
C4 C 0.7201(5) 1.13523(17) 0.23248(10) 0.0556(6) Uani 1 1 d . . . . .
C5 C 0.5734(4) 0.99938(15) 0.30611(9) 0.0429(5) Uani 1 1 d . . . . .
C6 C 0.4657(4) 1.06153(17) 0.35115(10) 0.0590(6) Uani 1 1 d . . . . .
H6 H 0.512203 1.128006 0.351914 0.071 Uiso 1 1 calc R U . . .
C7 C 0.2906(5) 1.02457(19) 0.39455(10) 0.0654(7) Uani 1 1 d . . . . .
H7 H 0.222722 1.066834 0.424653 0.078 Uiso 1 1 calc R U . . .
C8 C 0.2125(4) 0.92665(18) 0.39473(10) 0.0550(6) Uani 1 1 d . . . . .
C9 C 0.3253(4) 0.86541(17) 0.35129(10) 0.0529(6) Uani 1 1 d . . . . .
H9 H 0.281273 0.798693 0.351252 0.063 Uiso 1 1 calc R U . . .
C10 C 0.5024(4) 0.90071(16) 0.30773(9) 0.0484(5) Uani 1 1 d . . . . .
H10 H 0.575477 0.857373 0.278916 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0107(5) 0.8881(2) 0.44023(12) 0.0794(8) Uani 1 1 d . . . . .
H11A H -0.046888 0.823580 0.427563 0.119 Uiso 1 1 calc R U . . .
H11B H -0.139496 0.931907 0.441466 0.119 Uiso 1 1 calc R U . . .
H11C H 0.089727 0.884229 0.480698 0.119 Uiso 1 1 calc R U . . .
C12 C 1.2867(4) 0.94861(16) 0.14541(8) 0.0432(5) Uani 1 1 d . . . . .
C13 C 1.4605(4) 0.98866(17) 0.10194(9) 0.0503(5) Uani 1 1 d . . . . .
H13 H 1.454700 1.056118 0.093948 0.060 Uiso 1 1 calc R U . . .
C14 C 1.6412(4) 0.93062(18) 0.07039(9) 0.0530(6) Uani 1 1 d . . . . .
H14 H 1.754208 0.958897 0.041200 0.064 Uiso 1 1 calc R U . . .
C15 C 1.6540(4) 0.83082(17) 0.08219(9) 0.0482(5) Uani 1 1 d . . . . .
C16 C 1.4847(4) 0.78979(18) 0.12580(10) 0.0534(6) Uani 1 1 d . . . . .
H16 H 1.493338 0.722504 0.134231 0.064 Uiso 1 1 calc R U . . .
C17 C 1.3035(4) 0.84803(17) 0.15677(9) 0.0501(5) Uani 1 1 d . . . . .
H17 H 1.190432 0.819397 0.185817 0.060 Uiso 1 1 calc R U . . .
C18 C 1.9849(5) 0.8027(2) 0.00475(11) 0.0742(8) Uani 1 1 d . . . . .
H18A H 1.874613 0.829870 -0.027355 0.111 Uiso 1 1 calc R U . . .
H18B H 2.089807 0.749693 -0.011905 0.111 Uiso 1 1 calc R U . . .
H18C H 2.100641 0.853175 0.020607 0.111 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
O1 C4 1.202(3) . ?
O2 N1 1.407(2) . ?
O2 C4 1.368(2) . ?
O3 C15 1.362(2) . ?
O3 C18 1.423(3) . ?
N1 C1 1.291(3) . ?
C1 C2 1.435(3) . ?
C1 C12 1.482(3) . ?
C2 C3 1.340(3) . ?
C3 C4 1.459(3) . ?
C3 C5 1.477(2) . ?
C5 C6 1.394(3) . ?
C5 C10 1.383(3) . ?
C6 C7 1.378(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.373(3) . ?
C8 C11 1.504(3) . ?
C9 C10 1.379(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.377(3) . ?

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
C4 O2 N1 124.76(17) . . ?
C15 O3 C18 117.92(19) . . ?
C1 N1 O2 116.47(17) . . ?
N1 C1 C2 122.64(19) . . ?
N1 C1 C12 114.93(17) . . ?
C2 C1 C12 122.39(19) . . ?
C3 C2 C1 121.9(2) . . ?
C2 C3 C4 117.05(18) . . ?
C2 C3 C5 123.18(19) . . ?
C4 C3 C5 119.70(17) . . ?
O1 C4 O2 114.9(2) . . ?
O1 C4 C3 127.9(2) . . ?
O2 C4 C3 117.13(18) . . ?
C6 C5 C3 122.93(19) . . ?
C10 C5 C3 119.30(17) . . ?
C10 C5 C6 117.75(18) . . ?
C7 C6 C5 120.1(2) . . ?
C6 C7 C8 122.1(2) . . ?
C7 C8 C11 121.7(2) . . ?
C9 C8 C7 117.40(19) . . ?
C9 C8 C11 120.9(2) . . ?
C8 C9 C10 121.4(2) . . ?
C9 C10 C5 121.21(19) . . ?
C13 C12 C1 120.4(2) . . ?
C17 C12 C1 121.93(17) . . ?
C17 C12 C13 117.65(19) . . ?
C14 C13 C12 121.5(2) . . ?
C15 C14 C13 119.92(19) . . ?
O3 C15 C14 125.16(18) . . ?
O3 C15 C16 115.4(2) . . ?
C14 C15 C16 119.39(19) . . ?
C17 C16 C15 120.4(2) . . ?
C16 C17 C12 121.14(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.597
_oxdiff_exptl_absorpt_empirical_full_min 0.386
