# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_MS2BZU
_database_code_depnum_ccdc_archive 'CCDC 1909617'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
6-(2-Hydroxy-5-methylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
;
_chemical_formula_moiety         'C16 H13 N3 O4'
_chemical_formula_sum            'C16 H13 N3 O4'
_chemical_formula_iupac          'C16 H13 N3 O4'
_chemical_formula_weight         311.29

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                   8.1712(11)
_cell_length_b                   13.873(2)
_cell_length_c                   12.3934(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.098(6)
_cell_angle_gamma                90
_cell_volume                     1403.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2477
_cell_measurement_theta_min      2.937
_cell_measurement_theta_max      27.927
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.980
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.76
_diffrn_reflns_number            9802
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         27.927
_diffrn_reflns_theta_full        27.927
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3315
_reflns_number_gt                2477
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1006P)²+0.2367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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 0.13821(18) -0.00519(11) -0.13662(10) 0.0464(4) Uani 1 1 d . . . . .
H1 H 0.139(3) -0.0607(19) -0.094(2) 0.070 Uiso 1 1 d . U . . .
O2 O 0.17784(18) -0.10940(9) 0.03789(10) 0.0465(4) Uani 1 1 d . . . . .
O3 O 0.50640(17) -0.29279(9) 0.34097(10) 0.0449(4) Uani 1 1 d . . . . .
O4 O 0.47084(18) -0.16160(10) 0.67340(10) 0.0494(4) Uani 1 1 d . . . . .
N1 N 0.23550(18) 0.00831(10) 0.38912(11) 0.0354(4) Uani 1 1 d . . . . .
N2 N 0.49612(19) -0.22076(10) 0.50489(11) 0.0362(4) Uani 1 1 d . . . . .
H2A H 0.5624 -0.2638 0.5308 0.043 Uiso 1 1 calc R U . . .
N3 N 0.34345(18) -0.08042(10) 0.53406(11) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.2293(2) 0.06028(12) -0.08031(13) 0.0343(4) Uani 1 1 d . . . . .
C2 C 0.2742(2) 0.14314(14) -0.13389(14) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.2382 0.1528 -0.2051 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3715(2) 0.21118(13) -0.08288(15) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.4005 0.2660 -0.1208 0.050 Uiso 1 1 calc R U . . .
C4 C 0.4282(2) 0.20072(12) 0.02401(15) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.3790(2) 0.11937(12) 0.07872(14) 0.0353(4) Uani 1 1 d . . . . .
H5 H 0.4137 0.1112 0.1504 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2785(2) 0.04879(12) 0.02961(12) 0.0311(4) Uani 1 1 d . . . . .
C7 C 0.5423(3) 0.27321(14) 0.0767(2) 0.0537(5) Uani 1 1 d . . . . .
H7A H 0.6448 0.2427 0.0957 0.081 Uiso 1 1 calc R U . . .
H7B H 0.4945 0.2980 0.1407 0.081 Uiso 1 1 calc R U . . .
H7C H 0.5604 0.3252 0.0274 0.081 Uiso 1 1 calc R U . . .
C8 C 0.2334(2) -0.03859(12) 0.08730(13) 0.0322(4) Uani 1 1 d . . . . .
C9 C 0.26097(19) -0.04845(11) 0.20640(13) 0.0307(4) Uani 1 1 d . . . . .
C10 C 0.33305(19) -0.13246(12) 0.24479(13) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.3592 -0.1814 0.1971 0.037 Uiso 1 1 calc R U . . .
C11 C 0.36613(19) -0.14355(11) 0.35414(12) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.31409(19) -0.07093(11) 0.42381(13) 0.0291(3) Uani 1 1 d . . . . .
C13 C 0.2146(2) 0.01972(12) 0.28260(14) 0.0350(4) Uani 1 1 d . . . . .
H13 H 0.1663 0.0765 0.2575 0.042 Uiso 1 1 calc R U . . .
C14 C 0.4594(2) -0.22600(11) 0.39614(13) 0.0324(4) Uani 1 1 d . . . . .
C15 C 0.4390(2) -0.15433(12) 0.57768(14) 0.0353(4) Uani 1 1 d . . . . .
C16 C 0.2704(3) -0.01291(15) 0.60928(15) 0.0492(5) Uani 1 1 d . . . . .
H16A H 0.1540 -0.0109 0.5960 0.074 Uiso 1 1 calc R U . . .
H16B H 0.3154 0.0502 0.5992 0.074 Uiso 1 1 calc R U . . .
H16C H 0.2939 -0.0338 0.6821 0.074 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 C1 1.352(2) . ?
O1 H1 0.93(3) . ?
O2 C8 1.235(2) . ?
O3 C14 1.222(2) . ?
O4 C15 1.209(2) . ?
N1 C13 1.334(2) . ?
N1 C12 1.336(2) . ?
N2 C14 1.372(2) . ?
N2 C15 1.383(2) . ?
N2 H2A 0.8600 . ?
N3 C12 1.385(2) . ?
N3 C15 1.386(2) . ?
N3 C16 1.464(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.415(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 C7 1.504(3) . ?
C5 C6 1.403(2) . ?
C5 H5 0.9300 . ?
C6 C8 1.461(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.491(2) . ?
C9 C10 1.382(2) . ?
C9 C13 1.399(2) . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(2) . ?
C11 C14 1.460(2) . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 O1 H1 105.9(15) . . ?
C13 N1 C12 117.29(14) . . ?
C14 N2 C15 127.54(14) . . ?
C14 N2 H2A 116.2 . . ?
C15 N2 H2A 116.2 . . ?
C12 N3 C15 121.99(14) . . ?
C12 N3 C16 120.49(14) . . ?
C15 N3 C16 117.50(14) . . ?
O1 C1 C2 117.46(15) . . ?
O1 C1 C6 123.57(15) . . ?
C2 C1 C6 118.97(16) . . ?
C3 C2 C1 120.63(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 122.15(16) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 117.24(16) . . ?
C5 C4 C7 121.28(17) . . ?
C3 C4 C7 121.45(17) . . ?
C4 C5 C6 122.20(16) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 118.71(15) . . ?
C5 C6 C8 121.40(14) . . ?
C1 C6 C8 119.76(14) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C6 120.79(15) . . ?
O2 C8 C9 117.21(15) . . ?
C6 C8 C9 121.91(14) . . ?
C10 C9 C13 117.40(14) . . ?
C10 C9 C8 117.72(14) . . ?
C13 C9 C8 124.85(15) . . ?
C11 C10 C9 119.83(15) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 118.11(14) . . ?
C10 C11 C14 121.21(14) . . ?
C12 C11 C14 120.62(14) . . ?
N1 C12 N3 117.37(14) . . ?
N1 C12 C11 123.07(15) . . ?
N3 C12 C11 119.57(14) . . ?
N1 C13 C9 124.05(15) . . ?
N1 C13 H13 118.0 . . ?
C9 C13 H13 118.0 . . ?
O3 C14 N2 121.87(15) . . ?
O3 C14 C11 124.43(15) . . ?
N2 C14 C11 113.66(14) . . ?
O4 C15 N2 121.25(16) . . ?
O4 C15 N3 122.82(16) . . ?
N2 C15 N3 115.93(14) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 C1 C2 C3 -177.69(15) . . . . ?
C6 C1 C2 C3 3.0(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 C7 176.55(18) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C7 C4 C5 C6 -177.17(17) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C8 177.41(16) . . . . ?
O1 C1 C6 C5 177.21(15) . . . . ?
C2 C1 C6 C5 -3.5(2) . . . . ?
O1 C1 C6 C8 1.3(2) . . . . ?
C2 C1 C6 C8 -179.48(16) . . . . ?
C5 C6 C8 O2 -163.31(16) . . . . ?
C1 C6 C8 O2 12.5(2) . . . . ?
C5 C6 C8 C9 13.1(2) . . . . ?
C1 C6 C8 C9 -171.11(15) . . . . ?
O2 C8 C9 C10 43.8(2) . . . . ?
C6 C8 C9 C10 -132.72(16) . . . . ?
O2 C8 C9 C13 -134.09(18) . . . . ?
C6 C8 C9 C13 49.4(2) . . . . ?
C13 C9 C10 C11 -4.2(2) . . . . ?
C8 C9 C10 C11 177.83(14) . . . . ?
C9 C10 C11 C12 4.5(2) . . . . ?
C9 C10 C11 C14 -172.64(14) . . . . ?
C13 N1 C12 N3 176.69(14) . . . . ?
C13 N1 C12 C11 -3.6(2) . . . . ?
C15 N3 C12 N1 -172.92(14) . . . . ?
C16 N3 C12 N1 8.4(2) . . . . ?
C15 N3 C12 C11 7.4(2) . . . . ?
C16 N3 C12 C11 -171.25(16) . . . . ?
C10 C11 C12 N1 -0.5(2) . . . . ?
C14 C11 C12 N1 176.62(14) . . . . ?
C10 C11 C12 N3 179.17(14) . . . . ?
C14 C11 C12 N3 -3.7(2) . . . . ?
C12 N1 C13 C9 4.0(3) . . . . ?
C10 C9 C13 N1 -0.1(3) . . . . ?
C8 C9 C13 N1 177.72(16) . . . . ?
C15 N2 C14 O3 -173.78(16) . . . . ?
C15 N2 C14 C11 8.4(2) . . . . ?
C10 C11 C14 O3 -4.3(3) . . . . ?
C12 C11 C14 O3 178.66(16) . . . . ?
C10 C11 C14 N2 173.44(15) . . . . ?
C12 C11 C14 N2 -3.6(2) . . . . ?
C14 N2 C15 O4 174.34(16) . . . . ?
C14 N2 C15 N3 -5.2(3) . . . . ?
C12 N3 C15 O4 177.18(16) . . . . ?
C16 N3 C15 O4 -4.1(3) . . . . ?
C12 N3 C15 N2 -3.2(2) . . . . ?
C16 N3 C15 N2 175.43(15) . . . . ?

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
O1 H1 O2 0.93(3) 1.79(3) 2.6118(19) 145(2) .
O1 H1 O3 0.93(3) 2.42(2) 3.0117(19) 121.0(19) 4
N2 H2A O2 0.86 2.00 2.8070(19) 156.6 4_656
C13 H13 O3 0.93 2.58 3.488(2) 166.7 2
C16 H16C O1 0.96 2.65 3.368(2) 131.7 1_556

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_MS6BZU
_database_code_depnum_ccdc_archive 'CCDC 1909619'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
6-(2-Hydroxy-5-ethylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
;
_chemical_formula_moiety         'C17 H15 N3 O4'
_chemical_formula_sum            'C17 H15 N3 O4'
_chemical_formula_iupac          'C17 H15 N3 O4'
_chemical_formula_weight         325.32

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                   11.7250(5)
_cell_length_b                   13.3565(6)
_cell_length_c                   10.1992(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.332(2)
_cell_angle_gamma                90
_cell_volume                     1455.37(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      2.706
_cell_measurement_theta_max      27.915
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.975
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.76
_diffrn_reflns_number            8838
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         27.915
_diffrn_reflns_theta_full        27.915
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3413
_reflns_number_gt                2687
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.3184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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 0.57404(13) 0.45757(9) 0.25619(15) 0.0582(4) Uani 1 1 d . . . . .
H1 H 0.6193 0.4433 0.3398 0.087 Uiso 1 1 calc R U . . .
O2 O 0.68094(11) 0.33776(9) 0.47462(12) 0.0464(3) Uani 1 1 d . . . . .
O3 O 0.90040(11) 0.09151(9) 0.88372(10) 0.0436(3) Uani 1 1 d . . . . .
O4 O 1.00674(13) -0.20758(9) 0.75839(13) 0.0550(3) Uani 1 1 d . . . . .
N1 N 0.80933(11) 0.01708(10) 0.39407(12) 0.0350(3) Uani 1 1 d . . . . .
N2 N 0.95235(12) -0.05743(10) 0.81642(12) 0.0375(3) Uani 1 1 d . . . . .
H2A H 0.9861 -0.0749 0.9055 0.045 Uiso 1 1 calc R U . . .
N3 N 0.90814(11) -0.09735(9) 0.57660(12) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.52320(14) 0.37322(12) 0.18263(17) 0.0394(3) Uani 1 1 d . . . . .
C2 C 0.43626(15) 0.38296(14) 0.04031(19) 0.0483(4) Uani 1 1 d . . . . .
H2 H 0.4147 0.4462 -0.0005 0.058 Uiso 1 1 calc R U . . .
C3 C 0.38252(14) 0.29967(14) -0.03957(17) 0.0460(4) Uani 1 1 d . . . . .
H3 H 0.3259 0.3077 -0.1348 0.055 Uiso 1 1 calc R U . . .
C4 C 0.40974(13) 0.20330(12) 0.01703(16) 0.0393(4) Uani 1 1 d . . . . .
C5 C 0.49630(13) 0.19432(12) 0.15838(15) 0.0355(3) Uani 1 1 d . . . . .
H5 H 0.5146 0.1308 0.1992 0.043 Uiso 1 1 calc R U . . .
C6 C 0.55717(13) 0.27687(11) 0.24206(15) 0.0332(3) Uani 1 1 d . . . . .
C7 C 0.34775(15) 0.11249(14) -0.07002(18) 0.0487(4) Uani 1 1 d . . . . .
H7A H 0.4032 0.0555 -0.0343 0.058 Uiso 1 1 calc R U . . .
H7B H 0.3343 0.1235 -0.1693 0.058 Uiso 1 1 calc R U . . .
C8 C 0.22415(17) 0.08854(15) -0.0645(2) 0.0575(5) Uani 1 1 d . . . . .
H8A H 0.2358 0.0822 0.0339 0.086 Uiso 1 1 calc R U . . .
H8B H 0.1923 0.0267 -0.1142 0.086 Uiso 1 1 calc R U . . .
H8C H 0.1656 0.1414 -0.1098 0.086 Uiso 1 1 calc R U . . .
C9 C 0.65458(13) 0.26693(11) 0.39048(15) 0.0335(3) Uani 1 1 d . . . . .
C10 C 0.72330(12) 0.17068(11) 0.43997(14) 0.0317(3) Uani 1 1 d . . . . .
C11 C 0.74796(13) 0.10325(11) 0.35056(14) 0.0352(3) Uani 1 1 d . . . . .
H11 H 0.7196 0.1196 0.2536 0.042 Uiso 1 1 calc R U . . .
C12 C 0.85105(12) -0.00522(11) 0.53390(13) 0.0292(3) Uani 1 1 d . . . . .
C13 C 0.83982(12) 0.06060(11) 0.63474(13) 0.0292(3) Uani 1 1 d . . . . .
C14 C 0.77579(12) 0.14946(11) 0.58644(14) 0.0306(3) Uani 1 1 d . . . . .
H14 H 0.7679 0.1947 0.6515 0.037 Uiso 1 1 calc R U . . .
C15 C 0.89833(13) 0.03566(11) 0.78806(14) 0.0324(3) Uani 1 1 d . . . . .
C16 C 0.95900(13) -0.12644(12) 0.71911(15) 0.0356(3) Uani 1 1 d . . . . .
C17 C 0.91441(15) -0.16888(12) 0.47050(16) 0.0427(4) Uani 1 1 d . . . . .
H17A H 0.8355 -0.2027 0.4247 0.064 Uiso 1 1 calc R U . . .
H17B H 0.9791 -0.2171 0.5180 0.064 Uiso 1 1 calc R U . . .
H17C H 0.9327 -0.1337 0.3994 0.064 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 C1 1.349(2) . ?
O1 H1 0.8200 . ?
O2 C9 1.2281(18) . ?
O3 C15 1.2205(17) . ?
O4 C16 1.2098(18) . ?
N1 C11 1.3327(19) . ?
N1 C12 1.3368(17) . ?
N2 C15 1.3710(19) . ?
N2 C16 1.3800(19) . ?
N2 H2A 0.8600 . ?
N3 C16 1.3803(18) . ?
N3 C12 1.3826(18) . ?
N3 C17 1.4680(18) . ?
C1 C2 1.394(2) . ?
C1 C6 1.408(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 C7 1.502(2) . ?
C5 C6 1.397(2) . ?
C5 H5 0.9300 . ?
C6 C9 1.4795(19) . ?
C7 C8 1.507(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.491(2) . ?
C10 C14 1.3903(18) . ?
C10 C11 1.394(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3999(19) . ?
C13 C14 1.3821(19) . ?
C13 C15 1.4638(18) . ?
C14 H14 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 O1 H1 109.5 . . ?
C11 N1 C12 117.24(12) . . ?
C15 N2 C16 127.74(12) . . ?
C15 N2 H2A 116.1 . . ?
C16 N2 H2A 116.1 . . ?
C16 N3 C12 121.68(12) . . ?
C16 N3 C17 117.51(12) . . ?
C12 N3 C17 120.79(11) . . ?
O1 C1 C2 117.86(14) . . ?
O1 C1 C6 122.83(14) . . ?
C2 C1 C6 119.29(15) . . ?
C3 C2 C1 120.23(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 122.24(14) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 117.13(14) . . ?
C5 C4 C7 120.94(14) . . ?
C3 C4 C7 121.93(14) . . ?
C4 C5 C6 122.59(14) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 118.40(13) . . ?
C5 C6 C9 122.62(13) . . ?
C1 C6 C9 118.98(13) . . ?
C4 C7 C8 112.82(15) . . ?
C4 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C4 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C6 120.78(13) . . ?
O2 C9 C10 118.84(12) . . ?
C6 C9 C10 120.37(12) . . ?
C14 C10 C11 116.86(13) . . ?
C14 C10 C9 118.55(13) . . ?
C11 C10 C9 124.37(12) . . ?
N1 C11 C10 124.69(12) . . ?
N1 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
N1 C12 N3 116.82(12) . . ?
N1 C12 C13 122.69(13) . . ?
N3 C12 C13 120.49(12) . . ?
C14 C13 C12 118.63(12) . . ?
C14 C13 C15 121.53(12) . . ?
C12 C13 C15 119.82(13) . . ?
C13 C14 C10 119.54(13) . . ?
C13 C14 H14 120.2 . . ?
C10 C14 H14 120.2 . . ?
O3 C15 N2 122.03(12) . . ?
O3 C15 C13 124.13(13) . . ?
N2 C15 C13 113.84(12) . . ?
O4 C16 N2 121.05(13) . . ?
O4 C16 N3 122.76(14) . . ?
N2 C16 N3 116.20(13) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O1 C1 C2 C3 179.51(16) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 C7 178.28(16) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C7 C4 C5 C6 179.08(14) . . . . ?
C4 C5 C6 C1 4.0(2) . . . . ?
C4 C5 C6 C9 -176.65(13) . . . . ?
O1 C1 C6 C5 178.14(15) . . . . ?
C2 C1 C6 C5 -3.9(2) . . . . ?
O1 C1 C6 C9 -1.3(2) . . . . ?
C2 C1 C6 C9 176.67(14) . . . . ?
C5 C4 C7 C8 93.41(19) . . . . ?
C3 C4 C7 C8 -86.1(2) . . . . ?
C5 C6 C9 O2 -159.35(14) . . . . ?
C1 C6 C9 O2 20.0(2) . . . . ?
C5 C6 C9 C10 21.2(2) . . . . ?
C1 C6 C9 C10 -159.41(13) . . . . ?
O2 C9 C10 C14 25.1(2) . . . . ?
C6 C9 C10 C14 -155.45(13) . . . . ?
O2 C9 C10 C11 -149.35(15) . . . . ?
C6 C9 C10 C11 30.1(2) . . . . ?
C12 N1 C11 C10 -0.7(2) . . . . ?
C14 C10 C11 N1 5.5(2) . . . . ?
C9 C10 C11 N1 180.00(13) . . . . ?
C11 N1 C12 N3 176.33(12) . . . . ?
C11 N1 C12 C13 -4.3(2) . . . . ?
C16 N3 C12 N1 177.42(12) . . . . ?
C17 N3 C12 N1 -3.85(19) . . . . ?
C16 N3 C12 C13 -2.0(2) . . . . ?
C17 N3 C12 C13 176.78(13) . . . . ?
N1 C12 C13 C14 4.3(2) . . . . ?
N3 C12 C13 C14 -176.32(12) . . . . ?
N1 C12 C13 C15 -174.02(13) . . . . ?
N3 C12 C13 C15 5.31(19) . . . . ?
C12 C13 C14 C10 0.7(2) . . . . ?
C15 C13 C14 C10 179.04(12) . . . . ?
C11 C10 C14 C13 -5.2(2) . . . . ?
C9 C10 C14 C13 179.94(12) . . . . ?
C16 N2 C15 O3 -178.41(14) . . . . ?
C16 N2 C15 C13 1.3(2) . . . . ?
C14 C13 C15 O3 -3.4(2) . . . . ?
C12 C13 C15 O3 174.88(14) . . . . ?
C14 C13 C15 N2 176.83(12) . . . . ?
C12 C13 C15 N2 -4.85(18) . . . . ?
C15 N2 C16 O4 -177.95(14) . . . . ?
C15 N2 C16 N3 1.9(2) . . . . ?
C12 N3 C16 O4 178.22(14) . . . . ?
C17 N3 C16 O4 -0.6(2) . . . . ?
C12 N3 C16 N2 -1.6(2) . . . . ?
C17 N3 C16 N2 179.64(13) . . . . ?

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
O1 H1 O2 0.82 1.89 2.6065(17) 144.9 .
N2 H2A O3 0.86 2.02 2.8618(15) 165.5 3_757

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_MS4BZU
_database_code_depnum_ccdc_archive 'CCDC 1909620'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
6-(5-Fluoro-2-hydroxybenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
;
_chemical_formula_moiety         'C15 H10 F N3 O4'
_chemical_formula_sum            'C15 H10 F N3 O4'
_chemical_formula_iupac          'C15 H10 F N3 O4'
_chemical_formula_weight         315.26

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   23.336(3)
_cell_length_b                   6.9240(6)
_cell_length_c                   17.2853(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.798(3)
_cell_angle_gamma                90
_cell_volume                     2643.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2521
_cell_measurement_theta_min      3.083
_cell_measurement_theta_max      27.895
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.970
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.76
_diffrn_reflns_number            8315
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.083
_diffrn_reflns_theta_max         27.895
_diffrn_reflns_theta_full        27.895
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3120
_reflns_number_gt                2521
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+1.2647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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
F1 F 0.58458(5) 0.45657(14) 0.24286(6) 0.0571(3) Uani 1 1 d . . . . .
O1 O 0.48299(6) 1.11823(15) 0.08765(8) 0.0521(3) Uani 1 1 d . . . . .
H1 H 0.4563 1.0952 0.0444 0.078 Uiso 1 1 calc R U . . .
O2 O 0.40725(5) 0.90963(14) -0.01904(7) 0.0443(3) Uani 1 1 d . . . . .
O3 O 0.34538(6) 0.13333(16) 0.13653(6) 0.0490(3) Uani 1 1 d . . . . .
O4 O 0.23802(6) -0.16573(16) -0.09747(7) 0.0520(3) Uani 1 1 d . . . . .
N1 N 0.32772(6) 0.40910(18) -0.12315(7) 0.0402(3) Uani 1 1 d . . . . .
N2 N 0.28156(6) 0.12033(16) -0.11019(7) 0.0373(3) Uani 1 1 d . . . . .
N3 N 0.29043(6) -0.00814(17) 0.01819(7) 0.0362(3) Uani 1 1 d . . . . .
H3A H 0.2800 -0.0967 0.0459 0.043 Uiso 1 1 calc R U . . .
C1 C 0.50572(7) 0.9505(2) 0.12490(9) 0.0380(3) Uani 1 1 d . . . . .
C2 C 0.55577(8) 0.9607(2) 0.19547(10) 0.0468(4) Uani 1 1 d . . . . .
H2 H 0.5716 1.0805 0.2158 0.056 Uiso 1 1 calc R U . . .
C3 C 0.58172(8) 0.7962(2) 0.23498(9) 0.0455(4) Uani 1 1 d . . . . .
H3 H 0.6151 0.8029 0.2822 0.055 Uiso 1 1 calc R U . . .
C4 C 0.55757(7) 0.6193(2) 0.20353(9) 0.0392(3) Uani 1 1 d . . . . .
C5 C 0.50826(7) 0.6013(2) 0.13550(8) 0.0355(3) Uani 1 1 d . . . . .
H5 H 0.4934 0.4798 0.1162 0.043 Uiso 1 1 calc R U . . .
C6 C 0.48005(7) 0.76942(19) 0.09476(8) 0.0328(3) Uani 1 1 d . . . . .
C7 C 0.42568(7) 0.76276(19) 0.02285(8) 0.0333(3) Uani 1 1 d . . . . .
C8 C 0.38972(7) 0.58205(19) -0.00420(8) 0.0326(3) Uani 1 1 d . . . . .
C9 C 0.37803(6) 0.44309(19) 0.04657(8) 0.0318(3) Uani 1 1 d . . . . .
H9 H 0.3945 0.4542 0.1030 0.038 Uiso 1 1 calc R U . . .
C10 C 0.34139(6) 0.28729(19) 0.01187(8) 0.0305(3) Uani 1 1 d . . . . .
C11 C 0.31767(6) 0.27505(19) -0.07343(8) 0.0318(3) Uani 1 1 d . . . . .
C12 C 0.36220(7) 0.5575(2) -0.08834(8) 0.0387(3) Uani 1 1 d . . . . .
H12 H 0.3686 0.6529 -0.1225 0.046 Uiso 1 1 calc R U . . .
C13 C 0.25617(10) 0.1086(3) -0.19951(9) 0.0586(5) Uani 1 1 d . . . . .
H13A H 0.2309 -0.0037 -0.2145 0.088 Uiso 1 1 calc R U . . .
H13B H 0.2885 0.0997 -0.2224 0.088 Uiso 1 1 calc R U . . .
H13C H 0.2325 0.2221 -0.2201 0.088 Uiso 1 1 calc R U . . .
C14 C 0.26839(7) -0.0259(2) -0.06548(9) 0.0367(3) Uani 1 1 d . . . . .
C15 C 0.32732(6) 0.13598(19) 0.06247(8) 0.0336(3) 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
F1 C4 1.3613(17) . ?
O1 C1 1.3508(18) . ?
O1 H1 0.8200 . ?
O2 C7 1.2420(16) . ?
O3 C15 1.2120(17) . ?
O4 C14 1.2217(17) . ?
N1 C12 1.3241(19) . ?
N1 C11 1.3361(18) . ?
N2 C14 1.3677(19) . ?
N2 C11 1.3844(17) . ?
N2 C13 1.4670(18) . ?
N3 C14 1.3754(18) . ?
N3 C15 1.3776(18) . ?
N3 H3A 0.8600 . ?
C1 C2 1.393(2) . ?
C1 C6 1.4145(19) . ?
C2 C3 1.365(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(2) . ?
C5 C6 1.4091(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.463(2) . ?
C7 C8 1.4951(19) . ?
C8 C9 1.3873(19) . ?
C8 C12 1.3981(19) . ?
C9 C10 1.3871(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.4005(17) . ?
C10 C15 1.4682(19) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 O1 H1 109.5 . . ?
C12 N1 C11 116.98(12) . . ?
C14 N2 C11 121.87(11) . . ?
C14 N2 C13 117.75(12) . . ?
C11 N2 C13 120.38(12) . . ?
C14 N3 C15 127.17(12) . . ?
C14 N3 H3A 116.4 . . ?
C15 N3 H3A 116.4 . . ?
O1 C1 C2 117.60(13) . . ?
O1 C1 C6 122.13(14) . . ?
C2 C1 C6 120.26(14) . . ?
C3 C2 C1 120.48(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 118.88(14) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 F1 118.84(13) . . ?
C5 C4 C3 123.00(14) . . ?
F1 C4 C3 118.16(13) . . ?
C4 C5 C6 119.02(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.28(13) . . ?
C5 C6 C7 122.42(12) . . ?
C1 C6 C7 119.29(12) . . ?
O2 C7 C6 120.79(12) . . ?
O2 C7 C8 116.68(13) . . ?
C6 C7 C8 122.53(12) . . ?
C9 C8 C12 117.11(13) . . ?
C9 C8 C7 125.98(12) . . ?
C12 C8 C7 116.77(12) . . ?
C10 C9 C8 119.04(12) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 118.80(12) . . ?
C9 C10 C15 121.49(12) . . ?
C11 C10 C15 119.71(12) . . ?
N1 C11 N2 116.70(11) . . ?
N1 C11 C10 122.92(12) . . ?
N2 C11 C10 120.38(12) . . ?
N1 C12 C8 125.11(13) . . ?
N1 C12 H12 117.4 . . ?
C8 C12 H12 117.4 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 N2 122.28(13) . . ?
O4 C14 N3 120.85(13) . . ?
N2 C14 N3 116.86(12) . . ?
O3 C15 N3 121.22(12) . . ?
O3 C15 C10 124.86(13) . . ?
N3 C15 C10 113.92(11) . . ?

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
O1 C1 C2 C3 -178.54(15) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 F1 178.91(15) . . . . ?
F1 C4 C5 C6 179.79(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C1 2.3(2) . . . . ?
C4 C5 C6 C7 -177.91(13) . . . . ?
O1 C1 C6 C5 177.33(14) . . . . ?
C2 C1 C6 C5 -3.2(2) . . . . ?
O1 C1 C6 C7 -2.5(2) . . . . ?
C2 C1 C6 C7 176.98(14) . . . . ?
C5 C6 C7 O2 -168.86(13) . . . . ?
C1 C6 C7 O2 11.0(2) . . . . ?
C5 C6 C7 C8 11.0(2) . . . . ?
C1 C6 C7 C8 -169.17(13) . . . . ?
O2 C7 C8 C9 -142.18(15) . . . . ?
C6 C7 C8 C9 38.0(2) . . . . ?
O2 C7 C8 C12 33.42(19) . . . . ?
C6 C7 C8 C12 -146.45(14) . . . . ?
C12 C8 C9 C10 1.4(2) . . . . ?
C7 C8 C9 C10 177.01(13) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C15 -179.87(13) . . . . ?
C12 N1 C11 N2 179.95(13) . . . . ?
C12 N1 C11 C10 0.5(2) . . . . ?
C14 N2 C11 N1 179.71(14) . . . . ?
C13 N2 C11 N1 -0.1(2) . . . . ?
C14 N2 C11 C10 -0.8(2) . . . . ?
C13 N2 C11 C10 179.33(15) . . . . ?
C9 C10 C11 N1 -1.4(2) . . . . ?
C15 C10 C11 N1 178.80(13) . . . . ?
C9 C10 C11 N2 179.17(12) . . . . ?
C15 C10 C11 N2 -0.6(2) . . . . ?
C11 N1 C12 C8 1.5(2) . . . . ?
C9 C8 C12 N1 -2.5(2) . . . . ?
C7 C8 C12 N1 -178.47(14) . . . . ?
C11 N2 C14 O4 -177.83(14) . . . . ?
C13 N2 C14 O4 2.0(2) . . . . ?
C11 N2 C14 N3 2.9(2) . . . . ?
C13 N2 C14 N3 -177.26(15) . . . . ?
C15 N3 C14 O4 176.81(15) . . . . ?
C15 N3 C14 N2 -3.9(2) . . . . ?
C14 N3 C15 O3 -177.82(15) . . . . ?
C14 N3 C15 C10 2.5(2) . . . . ?
C9 C10 C15 O3 0.4(2) . . . . ?
C11 C10 C15 O3 -179.80(15) . . . . ?
C9 C10 C15 N3 -179.89(13) . . . . ?
C11 C10 C15 N3 -0.11(19) . . . . ?

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
O1 H1 O2 0.82 1.83 2.5515(16) 145.8 .
N3 H3A O4 0.86 1.98 2.8292(16) 169.3 7_545
C5 H5 O1 0.93 2.55 3.4504(18) 163.6 1_545

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_MS7BZUTRANSFORMED
_database_code_depnum_ccdc_archive 'CCDC 1909618'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-04-11 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
6-(2-Hydroxy-5-isopropylbenzoyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)
-dione
;
_chemical_formula_moiety         'C18 H17 N3 O4'
_chemical_formula_sum            'C18 H17 N3 O4'
_chemical_formula_iupac          'C18 H17 N3 O4'
_chemical_formula_weight         339.34

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.4030(4)
_cell_length_b                   9.6898(4)
_cell_length_c                   10.9110(7)
_cell_angle_alpha                105.870(2)
_cell_angle_beta                 98.586(2)
_cell_angle_gamma                102.351(4)
_cell_volume                     814.10(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      2.706
_cell_measurement_theta_max      27.915
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.985
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.78
_diffrn_reflns_number            8321
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             3154
_reflns_number_gt                2336
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+0.1335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

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 0.09735(15) -0.12476(16) 0.29694(14) 0.0569(4) Uani 1 1 d . . . . .
H1 H 0.1191 -0.0590 0.3676 0.085 Uiso 1 1 calc R U . . .
O2 O 0.28215(16) 0.11086(15) 0.48255(13) 0.0529(4) Uani 1 1 d . . . . .
O3 O 0.7874(2) 0.45467(16) 0.22115(13) 0.0670(5) Uani 1 1 d . . . . .
O4 O 1.06934(16) 0.84341(15) 0.57692(15) 0.0605(4) Uani 1 1 d . . . . .
N1 N 0.6889(2) 0.46952(17) 0.64183(14) 0.0447(4) Uani 1 1 d . . . . .
N2 N 0.92498(19) 0.64754(16) 0.40124(15) 0.0454(4) Uani 1 1 d . . . . .
H2 H 0.9775 0.6888 0.3530 0.055 Uiso 1 1 calc R U . . .
N3 N 0.88165(19) 0.65811(16) 0.60953(14) 0.0441(4) Uani 1 1 d . . . . .
C1 C 0.3899(2) -0.01488(18) 0.31132(17) 0.0377(4) Uani 1 1 d . . . . .
C2 C 0.2383(2) -0.1265(2) 0.25146(18) 0.0427(4) Uani 1 1 d . . . . .
C3 C 0.2324(3) -0.2418(2) 0.14235(19) 0.0534(5) Uani 1 1 d . . . . .
H3 H 0.1318 -0.3134 0.1004 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3736(3) -0.2522(2) 0.09487(19) 0.0530(5) Uani 1 1 d . . . . .
H4 H 0.3660 -0.3299 0.0200 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5280(2) -0.1491(2) 0.15609(17) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.5318(2) -0.03257(18) 0.26289(17) 0.0392(4) Uani 1 1 d . . . . .
H6 H 0.6332 0.0377 0.3049 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6873(3) -0.1584(2) 0.1086(2) 0.0536(5) Uani 1 1 d . . . . .
H7 H 0.7790 -0.1192 0.1863 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7208(3) -0.0588(3) 0.0258(2) 0.0729(7) Uani 1 1 d . . . . .
H8A H 0.6353 -0.0954 -0.0530 0.109 Uiso 1 1 calc R U . . .
H8B H 0.8276 -0.0579 0.0043 0.109 Uiso 1 1 calc R U . . .
H8C H 0.7208 0.0405 0.0733 0.109 Uiso 1 1 calc R U . . .
C9 C 0.6927(4) -0.3136(3) 0.0390(3) 0.0864(8) Uani 1 1 d . . . . .
H9A H 0.6091 -0.3538 -0.0410 0.130 Uiso 1 1 calc R U . . .
H9B H 0.6715 -0.3751 0.0936 0.130 Uiso 1 1 calc R U . . .
H9C H 0.8010 -0.3112 0.0199 0.130 Uiso 1 1 calc R U . . .
C10 C 0.3939(2) 0.11279(19) 0.42115(17) 0.0387(4) Uani 1 1 d . . . . .
C11 C 0.5311(2) 0.25316(18) 0.46130(17) 0.0365(4) Uani 1 1 d . . . . .
C12 C 0.6092(2) 0.31036(18) 0.37680(16) 0.0376(4) Uani 1 1 d . . . . .
H12 H 0.5831 0.2573 0.2881 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7264(2) 0.44684(18) 0.42431(16) 0.0351(4) Uani 1 1 d . . . . .
C14 C 0.7632(2) 0.52189(18) 0.55791(16) 0.0361(4) Uani 1 1 d . . . . .
C15 C 0.5755(2) 0.33937(19) 0.59253(17) 0.0419(4) Uani 1 1 d . . . . .
H15 H 0.5212 0.3026 0.6499 0.050 Uiso 1 1 calc R U . . .
C16 C 0.8114(2) 0.5127(2) 0.33800(18) 0.0435(4) Uani 1 1 d . . . . .
C17 C 0.9653(2) 0.7252(2) 0.53272(19) 0.0446(4) Uani 1 1 d . . . . .
C18 C 0.9163(3) 0.7398(2) 0.7490(2) 0.0653(6) Uani 1 1 d . . . . .
H18A H 0.8136 0.7302 0.7785 0.098 Uiso 1 1 calc R U . . .
H18B H 0.9679 0.8431 0.7636 0.098 Uiso 1 1 calc R U . . .
H18C H 0.9902 0.6998 0.7966 0.098 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 C2 1.353(2) . ?
O1 H1 0.8200 . ?
O2 C10 1.232(2) . ?
O3 C16 1.210(2) . ?
O4 C17 1.205(2) . ?
N1 C15 1.323(2) . ?
N1 C14 1.332(2) . ?
N2 C16 1.368(2) . ?
N2 C17 1.376(2) . ?
N2 H2 0.8600 . ?
N3 C17 1.377(2) . ?
N3 C14 1.384(2) . ?
N3 C18 1.462(2) . ?
C1 C6 1.399(2) . ?
C1 C2 1.412(2) . ?
C1 C10 1.458(2) . ?
C2 C3 1.378(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(2) . ?
C5 C7 1.517(3) . ?
C6 H6 0.9300 . ?
C7 C9 1.502(3) . ?
C7 C8 1.505(3) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.491(2) . ?
C11 C12 1.376(2) . ?
C11 C15 1.393(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(2) . ?
C13 C16 1.463(2) . ?
C15 H15 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O1 H1 109.5 . . ?
C15 N1 C14 116.70(15) . . ?
C16 N2 C17 127.81(16) . . ?
C16 N2 H2 116.1 . . ?
C17 N2 H2 116.1 . . ?
C17 N3 C14 122.24(15) . . ?
C17 N3 C18 117.44(16) . . ?
C14 N3 C18 120.25(16) . . ?
C6 C1 C2 118.09(16) . . ?
C6 C1 C10 122.46(15) . . ?
C2 C1 C10 119.45(16) . . ?
O1 C2 C3 118.26(16) . . ?
O1 C2 C1 122.48(16) . . ?
C3 C2 C1 119.25(17) . . ?
C4 C3 C2 120.71(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.71(18) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 117.07(18) . . ?
C6 C5 C7 119.55(17) . . ?
C4 C5 C7 123.37(17) . . ?
C5 C6 C1 122.98(16) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
C9 C7 C8 110.85(19) . . ?
C9 C7 C5 114.50(19) . . ?
C8 C7 C5 110.62(17) . . ?
C9 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C5 C7 H7 106.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C1 121.55(16) . . ?
O2 C10 C11 117.13(16) . . ?
C1 C10 C11 121.29(15) . . ?
C12 C11 C15 116.99(15) . . ?
C12 C11 C10 124.81(15) . . ?
C15 C11 C10 118.00(15) . . ?
C11 C12 C13 119.63(16) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 118.37(16) . . ?
C12 C13 C16 121.57(15) . . ?
C14 C13 C16 120.06(15) . . ?
N1 C14 N3 116.66(15) . . ?
N1 C14 C13 123.26(16) . . ?
N3 C14 C13 120.08(16) . . ?
N1 C15 C11 125.03(16) . . ?
N1 C15 H15 117.5 . . ?
C11 C15 H15 117.5 . . ?
O3 C16 N2 121.78(17) . . ?
O3 C16 C13 124.24(17) . . ?
N2 C16 C13 113.97(15) . . ?
O4 C17 N2 121.46(18) . . ?
O4 C17 N3 122.69(18) . . ?
N2 C17 N3 115.83(15) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C6 C1 C2 O1 175.25(16) . . . . ?
C10 C1 C2 O1 -4.1(3) . . . . ?
C6 C1 C2 C3 -4.9(3) . . . . ?
C10 C1 C2 C3 175.74(16) . . . . ?
O1 C2 C3 C4 -177.51(17) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C3 C4 C5 C7 178.63(18) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C7 C5 C6 C1 178.97(16) . . . . ?
C2 C1 C6 C5 3.5(3) . . . . ?
C10 C1 C6 C5 -177.18(16) . . . . ?
C6 C5 C7 C9 152.6(2) . . . . ?
C4 C5 C7 C9 -28.8(3) . . . . ?
C6 C5 C7 C8 -81.2(2) . . . . ?
C4 C5 C7 C8 97.3(2) . . . . ?
C6 C1 C10 O2 -162.36(16) . . . . ?
C2 C1 C10 O2 17.0(3) . . . . ?
C6 C1 C10 C11 19.6(2) . . . . ?
C2 C1 C10 C11 -161.06(15) . . . . ?
O2 C10 C11 C12 -143.06(17) . . . . ?
C1 C10 C11 C12 35.1(2) . . . . ?
O2 C10 C11 C15 31.7(2) . . . . ?
C1 C10 C11 C15 -150.19(16) . . . . ?
C15 C11 C12 C13 0.5(2) . . . . ?
C10 C11 C12 C13 175.31(15) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C12 C13 C16 -179.40(15) . . . . ?
C15 N1 C14 N3 179.94(15) . . . . ?
C15 N1 C14 C13 0.1(3) . . . . ?
C17 N3 C14 N1 -178.99(15) . . . . ?
C18 N3 C14 N1 -2.0(3) . . . . ?
C17 N3 C14 C13 0.8(3) . . . . ?
C18 N3 C14 C13 177.80(17) . . . . ?
C12 C13 C14 N1 -1.1(3) . . . . ?
C16 C13 C14 N1 179.01(15) . . . . ?
C12 C13 C14 N3 179.13(14) . . . . ?
C16 C13 C14 N3 -0.8(2) . . . . ?
C14 N1 C15 C11 1.3(3) . . . . ?
C12 C11 C15 N1 -1.6(3) . . . . ?
C10 C11 C15 N1 -176.73(15) . . . . ?
C17 N2 C16 O3 -179.50(18) . . . . ?
C17 N2 C16 C13 -0.4(3) . . . . ?
C12 C13 C16 O3 -0.3(3) . . . . ?
C14 C13 C16 O3 179.62(18) . . . . ?
C12 C13 C16 N2 -179.34(15) . . . . ?
C14 C13 C16 N2 0.6(2) . . . . ?
C16 N2 C17 O4 179.44(17) . . . . ?
C16 N2 C17 N3 0.4(3) . . . . ?
C14 N3 C17 O4 -179.59(17) . . . . ?
C18 N3 C17 O4 3.3(3) . . . . ?
C14 N3 C17 N2 -0.6(3) . . . . ?
C18 N3 C17 N2 -177.67(17) . . . . ?

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
O1 H1 O2 0.82 1.89 2.5963(18) 144.4 .
N2 H2 O1 0.86 2.16 2.960(2) 154.6 1_665
C18 H18C O3 0.96 2.63 3.458(3) 144.6 2_766

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.057

