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

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

data_101
_database_code_depnum_ccdc_archive 'CCDC 2133239'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry,Sardar Patel University, Vallabh Vidyanagar, Gujarat, India
India
;
_audit_update_record             
;
2022-01-08 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-(4-chlorophenyl)-2,4-dimethoxy-8,8-dimethyl-5,8,9,10-tetrahydropyrimido[4,5-b]quinolin-6(7H)-one
_chemical_name_common            ?
_chemical_melting_point          208-210
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cl N3 O3'
_chemical_formula_weight         399.86

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'
Cl Cl 0.1484 0.1585 '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                   6.1119(17)
_cell_length_b                   12.856(3)
_cell_length_c                   13.503(2)
_cell_angle_alpha                74.018(10)
_cell_angle_beta                 83.479(15)
_cell_angle_gamma                76.619(15)
_cell_volume                     990.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1693
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      26.43

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4723
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.571
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.684
_diffrn_measured_fraction_theta_full 0.684
_diffrn_reflns_Laue_measured_fraction_max 0.684
_diffrn_reflns_Laue_measured_fraction_full 0.684
_diffrn_reflns_point_group_measured_fraction_max 0.684
_diffrn_reflns_point_group_measured_fraction_full 0.684
_reflns_number_total             2395
_reflns_number_gt                1393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+1.2597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.2058
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0385(11) 0.8262(4) 0.5020(3) 0.0296(13) Uani 1 1 d . . . . .
C2 C 0.0368(11) 0.7544(4) 0.6108(3) 0.0356(14) Uani 1 1 d . . . . .
H2A H -0.1117 0.7378 0.6298 0.043 Uiso 1 1 calc R U . . .
H2B H 0.0652 0.7951 0.6571 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2126(12) 0.6453(4) 0.6253(3) 0.0406(15) Uani 1 1 d . . . . .
C4 C 0.4377(12) 0.6723(4) 0.5767(4) 0.0437(15) Uani 1 1 d . . . . .
H4A H 0.4914 0.7114 0.6178 0.052 Uiso 1 1 calc R U . . .
H4B H 0.5463 0.6034 0.5795 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4294(12) 0.7408(4) 0.4670(4) 0.0390(14) Uani 1 1 d . . . . .
C6 C 0.2112(11) 0.8166(4) 0.4348(3) 0.0328(14) Uani 1 1 d . . . . .
C7 C 0.2048(11) 0.8793(4) 0.3225(3) 0.0340(14) Uani 1 1 d . . . . .
H7 H 0.3341 0.9152 0.3042 0.041 Uiso 1 1 calc R U . . .
C8 C -0.0102(12) 0.9675(4) 0.3051(3) 0.0352(15) Uani 1 1 d . . . . .
C9 C -0.0527(13) 1.0426(4) 0.2102(3) 0.0373(15) Uani 1 1 d . . . . .
C10 C -0.3984(13) 1.1105(4) 0.2694(3) 0.0396(16) Uani 1 1 d . . . . .
C11 C -0.1838(11) 0.9731(4) 0.3809(3) 0.0311(14) Uani 1 1 d . . . . .
C12 C 0.2192(11) 0.7994(4) 0.2546(3) 0.0355(14) Uani 1 1 d . . . . .
C13 C 0.4022(12) 0.7789(4) 0.1878(3) 0.0466(16) Uani 1 1 d . . . . .
H13 H 0.5214 0.8141 0.1829 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4094(14) 0.7060(5) 0.1278(4) 0.057(2) Uani 1 1 d . . . . .
H14 H 0.5343 0.6914 0.0837 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2312(15) 0.6557(4) 0.1339(4) 0.0503(19) Uani 1 1 d . . . . .
C16 C 0.0534(14) 0.6732(4) 0.2005(4) 0.0504(19) Uani 1 1 d . . . . .
H16 H -0.0630 0.6360 0.2062 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0427(12) 0.7467(4) 0.2609(3) 0.0423(15) Uani 1 1 d . . . . .
H17 H -0.0825 0.7603 0.3052 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0585(15) 1.1158(5) 0.0351(3) 0.059(2) Uani 1 1 d . . . . .
H18A H -0.0662 1.1002 0.0087 0.088 Uiso 1 1 calc R U . . .
H18B H 0.1885 1.1069 -0.0113 0.088 Uiso 1 1 calc R U . . .
H18C H 0.0213 1.1905 0.0415 0.088 Uiso 1 1 calc R U . . .
C19 C -0.6395(15) 1.2532(5) 0.1547(4) 0.065(2) Uani 1 1 d . . . . .
H19A H -0.5483 1.3075 0.1428 0.098 Uiso 1 1 calc R U . . .
H19B H -0.7953 1.2896 0.1499 0.098 Uiso 1 1 calc R U . . .
H19C H -0.5983 1.2116 0.1038 0.098 Uiso 1 1 calc R U . . .
C20 C 0.2329(14) 0.5900(5) 0.7408(4) 0.0563(19) Uani 1 1 d . . . . .
H20A H 0.3421 0.5215 0.7503 0.084 Uiso 1 1 calc R U . . .
H20B H 0.0895 0.5755 0.7711 0.084 Uiso 1 1 calc R U . . .
H20C H 0.2799 0.6381 0.7735 0.084 Uiso 1 1 calc R U . . .
C21 C 0.1398(16) 0.5667(5) 0.5738(4) 0.060(2) Uani 1 1 d . . . . .
H21A H 0.1313 0.5997 0.5010 0.090 Uiso 1 1 calc R U . . .
H21B H -0.0052 0.5535 0.6028 0.090 Uiso 1 1 calc R U . . .
H21C H 0.2479 0.4978 0.5856 0.090 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2381(5) 0.56864(13) 0.05546(12) 0.0892(10) Uani 1 1 d . . . . .
N1 N -0.1602(10) 0.9037(3) 0.4772(3) 0.0344(12) Uani 1 1 d . . . . .
N2 N -0.2508(10) 1.1154(3) 0.1903(3) 0.0401(13) Uani 1 1 d . . . . .
N3 N -0.3836(10) 1.0461(3) 0.3643(3) 0.0365(12) Uani 1 1 d . . . . .
O1 O 0.5919(9) 0.7342(4) 0.4087(3) 0.0635(13) Uani 1 1 d . . . . .
O2 O 0.1065(9) 1.0406(3) 0.1350(2) 0.0478(12) Uani 1 1 d . . . . .
O3 O -0.6045(9) 1.1801(3) 0.2550(3) 0.0542(14) Uani 1 1 d . . . . .
H1N H -0.262(13) 0.910(4) 0.522(4) 0.037(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.318(8) . ?
C1 N1 1.388(7) . ?
C1 C2 1.505(6) . ?
C2 C3 1.536(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.528(9) . ?
C3 C20 1.531(6) . ?
C3 C21 1.539(7) . ?
C4 C5 1.501(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.198(8) . ?
C5 C6 1.488(8) . ?
C6 C7 1.508(6) . ?
C7 C8 1.517(9) . ?
C7 C12 1.537(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.385(6) . ?
C8 C11 1.392(8) . ?
C9 O2 1.326(7) . ?
C9 N2 1.351(8) . ?
C10 N2 1.315(8) . ?
C10 N3 1.320(6) . ?
C10 O3 1.365(8) . ?
C11 N3 1.356(8) . ?
C11 N1 1.360(6) . ?
C12 C13 1.378(8) . ?
C12 C17 1.384(8) . ?
C13 C14 1.388(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.347(10) . ?
C15 Cl1 1.731(5) . ?
C16 C17 1.396(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.442(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O3 1.427(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1N 0.82(7) . ?

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
C6 C1 N1 122.2(4) . . ?
C6 C1 C2 123.6(5) . . ?
N1 C1 C2 114.2(5) . . ?
C1 C2 C3 113.1(4) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C20 110.1(5) . . ?
C4 C3 C2 108.0(4) . . ?
C20 C3 C2 109.2(5) . . ?
C4 C3 C21 110.5(5) . . ?
C20 C3 C21 108.9(5) . . ?
C2 C3 C21 110.2(5) . . ?
C5 C4 C3 114.6(5) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
O1 C5 C6 122.1(5) . . ?
O1 C5 C4 121.0(6) . . ?
C6 C5 C4 116.9(5) . . ?
C1 C6 C5 120.7(5) . . ?
C1 C6 C7 123.8(5) . . ?
C5 C6 C7 115.5(5) . . ?
C6 C7 C8 109.6(4) . . ?
C6 C7 C12 110.2(4) . . ?
C8 C7 C12 110.5(5) . . ?
C6 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C12 C7 H7 108.9 . . ?
C9 C8 C11 115.7(5) . . ?
C9 C8 C7 121.9(5) . . ?
C11 C8 C7 122.2(4) . . ?
O2 C9 N2 118.7(4) . . ?
O2 C9 C8 118.3(6) . . ?
N2 C9 C8 123.0(5) . . ?
N2 C10 N3 130.4(6) . . ?
N2 C10 O3 117.8(5) . . ?
N3 C10 O3 111.8(6) . . ?
N3 C11 N1 116.2(5) . . ?
N3 C11 C8 123.0(4) . . ?
N1 C11 C8 120.8(5) . . ?
C13 C12 C17 119.2(5) . . ?
C13 C12 C7 122.0(6) . . ?
C17 C12 C7 118.8(5) . . ?
C12 C13 C14 120.3(7) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.7(7) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.6(5) . . ?
C16 C15 Cl1 120.2(6) . . ?
C14 C15 Cl1 119.2(6) . . ?
C15 C16 C17 120.5(7) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.7(6) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N1 C1 120.6(5) . . ?
C11 N1 H1N 120(4) . . ?
C1 N1 H1N 120(4) . . ?
C10 N2 C9 114.2(5) . . ?
C10 N3 C11 113.7(5) . . ?
C9 O2 C18 118.2(5) . . ?
C10 O3 C19 116.5(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 C3 -20.4(7) . . . . ?
N1 C1 C2 C3 158.7(4) . . . . ?
C1 C2 C3 C4 48.4(5) . . . . ?
C1 C2 C3 C20 168.1(5) . . . . ?
C1 C2 C3 C21 -72.4(6) . . . . ?
C20 C3 C4 C5 -171.9(4) . . . . ?
C2 C3 C4 C5 -52.8(6) . . . . ?
C21 C3 C4 C5 67.8(6) . . . . ?
C3 C4 C5 O1 -151.9(6) . . . . ?
C3 C4 C5 C6 28.2(7) . . . . ?
N1 C1 C6 C5 173.7(4) . . . . ?
C2 C1 C6 C5 -7.3(7) . . . . ?
N1 C1 C6 C7 -6.2(8) . . . . ?
C2 C1 C6 C7 172.8(4) . . . . ?
O1 C5 C6 C1 -176.5(6) . . . . ?
C4 C5 C6 C1 3.5(7) . . . . ?
O1 C5 C6 C7 3.4(8) . . . . ?
C4 C5 C6 C7 -176.6(4) . . . . ?
C1 C6 C7 C8 10.1(7) . . . . ?
C5 C6 C7 C8 -169.8(4) . . . . ?
C1 C6 C7 C12 -111.6(6) . . . . ?
C5 C6 C7 C12 68.5(6) . . . . ?
C6 C7 C8 C9 175.4(4) . . . . ?
C12 C7 C8 C9 -63.0(6) . . . . ?
C6 C7 C8 C11 -9.3(7) . . . . ?
C12 C7 C8 C11 112.2(5) . . . . ?
C11 C8 C9 O2 -179.7(5) . . . . ?
C7 C8 C9 O2 -4.2(7) . . . . ?
C11 C8 C9 N2 -1.6(7) . . . . ?
C7 C8 C9 N2 174.0(5) . . . . ?
C9 C8 C11 N3 0.5(7) . . . . ?
C7 C8 C11 N3 -175.0(4) . . . . ?
C9 C8 C11 N1 -179.7(4) . . . . ?
C7 C8 C11 N1 4.8(7) . . . . ?
C6 C7 C12 C13 -113.7(6) . . . . ?
C8 C7 C12 C13 125.1(6) . . . . ?
C6 C7 C12 C17 66.4(7) . . . . ?
C8 C7 C12 C17 -54.9(6) . . . . ?
C17 C12 C13 C14 -0.2(8) . . . . ?
C7 C12 C13 C14 179.9(5) . . . . ?
C12 C13 C14 C15 1.1(8) . . . . ?
C13 C14 C15 C16 -2.5(9) . . . . ?
C13 C14 C15 Cl1 177.8(4) . . . . ?
C14 C15 C16 C17 3.0(9) . . . . ?
Cl1 C15 C16 C17 -177.4(4) . . . . ?
C13 C12 C17 C16 0.6(8) . . . . ?
C7 C12 C17 C16 -179.5(5) . . . . ?
C15 C16 C17 C12 -2.0(9) . . . . ?
N3 C11 N1 C1 -179.7(4) . . . . ?
C8 C11 N1 C1 0.5(7) . . . . ?
C6 C1 N1 C11 0.2(7) . . . . ?
C2 C1 N1 C11 -179.0(4) . . . . ?
N3 C10 N2 C9 -0.1(8) . . . . ?
O3 C10 N2 C9 -178.8(4) . . . . ?
O2 C9 N2 C10 179.5(5) . . . . ?
C8 C9 N2 C10 1.4(7) . . . . ?
N2 C10 N3 C11 -0.8(8) . . . . ?
O3 C10 N3 C11 178.0(4) . . . . ?
N1 C11 N3 C10 -179.3(4) . . . . ?
C8 C11 N3 C10 0.5(7) . . . . ?
N2 C9 O2 C18 -0.7(7) . . . . ?
C8 C9 O2 C18 177.5(5) . . . . ?
N2 C10 O3 C19 -0.7(7) . . . . ?
N3 C10 O3 C19 -179.6(5) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049


# start Validation Reply Form
_vrf_PLAT029_101                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.684 Why?  
RESPONSE: Even though crystal data was attempted to collected up to 0.78 \%A 
resolution, the crystal (the largest available) still diffracted quite weakly 
at high angle.  
 
;
# start Validation Reply Form
_vrf_PLAT911_101                 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595       1109 Report
RESPONSE:These reflections were probably affected by unexpected deviations
in their intensities for symmetry equivalent measurements and omitted during
initial data reduction.

  
;
# end Validation Reply Form
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and Dichloromethane'
_chemical_compound_source        NIL
####################################################################### 
# 
# 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_105
_database_code_depnum_ccdc_archive 'CCDC 2157100'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar
India
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4-dimethoxy-5-(3-methoxyphenyl)-8,8-dimethyl-5,8,9,10-tetrahydropyrimido[4,5-b]quinolin-6(7H)-one
_chemical_name_common            ?
_chemical_melting_point          497-499
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N3 O4'
_chemical_formula_weight         395.46

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                   12.5837(13)
_cell_length_b                   13.0752(17)
_cell_length_c                   13.0356(16)
_cell_angle_alpha                90
_cell_angle_beta                 110.844(5)
_cell_angle_gamma                90
_cell_volume                     2004.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2783
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.54

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12334
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3528
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.2309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0070(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3528
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.61383(16) 0.70269(17) 0.45526(15) 0.0450(5) Uani 1 1 d . . . . .
H1A H 0.6457 0.7470 0.4139 0.054 Uiso 1 1 calc R U . . .
H1B H 0.5515 0.6651 0.4030 0.054 Uiso 1 1 calc R U . . .
C2 C 0.70525(15) 0.62665(16) 0.52118(15) 0.0424(5) Uani 1 1 d . . . . .
C3 C 0.79101(15) 0.68594(18) 0.61514(16) 0.0491(6) Uani 1 1 d . . . . .
H3A H 0.8435 0.6374 0.6636 0.059 Uiso 1 1 calc R U . . .
H3B H 0.8346 0.7298 0.5848 0.059 Uiso 1 1 calc R U . . .
C4 C 0.74222(14) 0.75083(16) 0.68271(15) 0.0385(5) Uani 1 1 d . . . . .
C5 C 0.62693(13) 0.78757(15) 0.63256(14) 0.0346(5) Uani 1 1 d . . . . .
C6 C 0.57655(13) 0.85061(15) 0.70235(14) 0.0347(5) Uani 1 1 d . . . . .
H6 H 0.6344 0.8996 0.7448 0.042 Uiso 1 1 calc R U . . .
C7 C 0.47544(13) 0.91068(15) 0.62816(14) 0.0341(5) Uani 1 1 d . . . . .
C8 C 0.42323(14) 0.98908(16) 0.66499(15) 0.0367(5) Uani 1 1 d . . . . .
C9 C 0.28457(14) 1.00221(16) 0.50067(16) 0.0374(5) Uani 1 1 d . . . . .
C10 C 0.42116(13) 0.88604(15) 0.51904(14) 0.0354(5) Uani 1 1 d . . . . .
C11 C 0.56805(14) 0.76759(16) 0.52505(14) 0.0368(5) Uani 1 1 d . . . . .
C12 C 0.76420(19) 0.5796(2) 0.44842(18) 0.0650(7) Uani 1 1 d . . . . .
H12A H 0.8205 0.5314 0.4904 0.098 Uiso 1 1 calc R U . . .
H12B H 0.8002 0.6326 0.4215 0.098 Uiso 1 1 calc R U . . .
H12C H 0.7090 0.5452 0.3876 0.098 Uiso 1 1 calc R U . . .
C13 C 0.65230(19) 0.54090(19) 0.56589(19) 0.0649(7) Uani 1 1 d . . . . .
H13A H 0.6026 0.5013 0.5060 0.097 Uiso 1 1 calc R U . . .
H13B H 0.6096 0.5696 0.6070 0.097 Uiso 1 1 calc R U . . .
H13C H 0.7113 0.4977 0.6129 0.097 Uiso 1 1 calc R U . . .
C14 C 0.54366(13) 0.78474(15) 0.78332(14) 0.0350(5) Uani 1 1 d . . . . .
C15 C 0.61513(14) 0.77660(16) 0.89173(14) 0.0384(5) Uani 1 1 d . . . . .
H15 H 0.6842 0.8112 0.9152 0.046 Uiso 1 1 calc R U . . .
C16 C 0.58568(15) 0.71769(17) 0.96604(15) 0.0419(5) Uani 1 1 d . . . . .
C17 C 0.48304(16) 0.66694(18) 0.93348(18) 0.0519(6) Uani 1 1 d . . . . .
H17 H 0.4622 0.6283 0.9832 0.062 Uiso 1 1 calc R U . . .
C18 C 0.41171(16) 0.67496(19) 0.82501(19) 0.0582(6) Uani 1 1 d . . . . .
H18 H 0.3422 0.6410 0.8020 0.070 Uiso 1 1 calc R U . . .
C19 C 0.44098(15) 0.73187(18) 0.75024(17) 0.0495(6) Uani 1 1 d . . . . .
H19 H 0.3920 0.7350 0.6775 0.059 Uiso 1 1 calc R U . . .
C20 C 0.41675(17) 1.08945(19) 0.81503(17) 0.0547(6) Uani 1 1 d . . . . .
H20A H 0.4077 1.1520 0.7743 0.082 Uiso 1 1 calc R U . . .
H20B H 0.4612 1.1021 0.8908 0.082 Uiso 1 1 calc R U . . .
H20C H 0.3434 1.0637 0.8092 0.082 Uiso 1 1 calc R U . . .
C21 C 0.13307(16) 1.01571(19) 0.32938(16) 0.0519(6) Uani 1 1 d . . . . .
H21A H 0.1830 1.0292 0.2899 0.078 Uiso 1 1 calc R U . . .
H21B H 0.0631 1.0523 0.2958 0.078 Uiso 1 1 calc R U . . .
H21C H 0.1176 0.9437 0.3277 0.078 Uiso 1 1 calc R U . . .
N1 N 0.46398(12) 0.81063(13) 0.47106(12) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.4246 0.7902 0.4059 0.050 Uiso 1 1 calc R U . . .
N2 N 0.32538(11) 0.93179(13) 0.45220(12) 0.0388(4) Uani 1 1 d . . . . .
N3 N 0.32833(12) 1.03602(13) 0.60398(12) 0.0405(4) Uani 1 1 d . . . . .
O1 O 0.18625(10) 1.04865(12) 0.44167(10) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.47352(10) 1.01553(11) 0.77147(10) 0.0467(4) Uani 1 1 d . . . . .
O3 O 0.66504(12) 0.71479(13) 1.07065(10) 0.0594(5) Uani 1 1 d . . . . .
O4 O 0.80193(10) 0.77483(11) 0.77722(10) 0.0457(4) Uani 1 1 d . . . . .
C22 C 0.6455(2) 0.6475(2) 1.14745(18) 0.0684(7) Uani 1 1 d . . . . .
H22A H 0.5788 0.6689 1.1612 0.103 Uiso 1 1 calc R U . . .
H22B H 0.7099 0.6488 1.2148 0.103 Uiso 1 1 calc R U . . .
H22C H 0.6347 0.5793 1.1183 0.103 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
C1 C11 1.501(3) . ?
C1 C2 1.532(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C13 1.522(3) . ?
C2 C3 1.525(3) . ?
C2 C12 1.526(3) . ?
C3 C4 1.502(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.234(2) . ?
C4 C5 1.445(2) . ?
C5 C11 1.357(2) . ?
C5 C6 1.523(2) . ?
C6 C7 1.515(2) . ?
C6 C14 1.529(2) . ?
C6 H6 0.9800 . ?
C7 C10 1.379(2) . ?
C7 C8 1.392(3) . ?
C8 N3 1.326(2) . ?
C8 O2 1.350(2) . ?
C9 N2 1.320(2) . ?
C9 N3 1.336(2) . ?
C9 O1 1.347(2) . ?
C10 N2 1.350(2) . ?
C10 N1 1.376(2) . ?
C11 N1 1.368(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.383(2) . ?
C14 C19 1.392(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9300 . ?
C16 O3 1.374(2) . ?
C16 C17 1.378(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.434(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O1 1.442(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1 0.8600 . ?
O3 C22 1.418(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C11 C1 C2 113.61(15) . . ?
C11 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C11 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C13 C2 C3 110.36(17) . . ?
C13 C2 C12 108.48(19) . . ?
C3 C2 C12 110.03(16) . . ?
C13 C2 C1 110.44(16) . . ?
C3 C2 C1 107.23(17) . . ?
C12 C2 C1 110.30(16) . . ?
C4 C3 C2 115.97(15) . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
O4 C4 C5 121.60(18) . . ?
O4 C4 C3 119.89(16) . . ?
C5 C4 C3 118.45(16) . . ?
C11 C5 C4 119.64(17) . . ?
C11 C5 C6 122.05(15) . . ?
C4 C5 C6 118.29(15) . . ?
C7 C6 C5 109.44(14) . . ?
C7 C6 C14 111.14(13) . . ?
C5 C6 C14 112.33(16) . . ?
C7 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C14 C6 H6 107.9 . . ?
C10 C7 C8 113.98(16) . . ?
C10 C7 C6 122.17(17) . . ?
C8 C7 C6 123.63(16) . . ?
N3 C8 O2 119.38(17) . . ?
N3 C8 C7 124.66(17) . . ?
O2 C8 C7 115.93(16) . . ?
N2 C9 N3 128.50(16) . . ?
N2 C9 O1 118.43(17) . . ?
N3 C9 O1 113.07(17) . . ?
N2 C10 N1 115.36(16) . . ?
N2 C10 C7 124.26(18) . . ?
N1 C10 C7 120.38(16) . . ?
C5 C11 N1 121.53(17) . . ?
C5 C11 C1 123.26(16) . . ?
N1 C11 C1 115.12(15) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.21(18) . . ?
C15 C14 C6 120.76(16) . . ?
C19 C14 C6 121.03(16) . . ?
C14 C15 C16 121.21(17) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
O3 C16 C17 124.25(19) . . ?
O3 C16 C15 115.33(17) . . ?
C17 C16 C15 120.42(18) . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 121.67(19) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 120.13(19) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N1 C10 121.27(15) . . ?
C11 N1 H1 119.4 . . ?
C10 N1 H1 119.4 . . ?
C9 N2 C10 114.23(16) . . ?
C8 N3 C9 114.30(16) . . ?
C9 O1 C21 116.44(16) . . ?
C8 O2 C20 117.56(14) . . ?
C16 O3 C22 118.05(17) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C11 C1 C2 C13 71.7(2) . . . . ?
C11 C1 C2 C3 -48.6(2) . . . . ?
C11 C1 C2 C12 -168.44(18) . . . . ?
C13 C2 C3 C4 -70.1(2) . . . . ?
C12 C2 C3 C4 170.21(18) . . . . ?
C1 C2 C3 C4 50.2(2) . . . . ?
C2 C3 C4 O4 157.24(19) . . . . ?
C2 C3 C4 C5 -25.6(3) . . . . ?
O4 C4 C5 C11 173.56(19) . . . . ?
C3 C4 C5 C11 -3.5(3) . . . . ?
O4 C4 C5 C6 -4.7(3) . . . . ?
C3 C4 C5 C6 178.17(17) . . . . ?
C11 C5 C6 C7 -17.6(3) . . . . ?
C4 C5 C6 C7 160.63(16) . . . . ?
C11 C5 C6 C14 106.3(2) . . . . ?
C4 C5 C6 C14 -75.4(2) . . . . ?
C5 C6 C7 C10 17.6(2) . . . . ?
C14 C6 C7 C10 -107.08(19) . . . . ?
C5 C6 C7 C8 -168.08(17) . . . . ?
C14 C6 C7 C8 67.3(2) . . . . ?
C10 C7 C8 N3 1.6(3) . . . . ?
C6 C7 C8 N3 -173.20(17) . . . . ?
C10 C7 C8 O2 179.89(16) . . . . ?
C6 C7 C8 O2 5.1(3) . . . . ?
C8 C7 C10 N2 -0.6(3) . . . . ?
C6 C7 C10 N2 174.29(16) . . . . ?
C8 C7 C10 N1 179.28(16) . . . . ?
C6 C7 C10 N1 -5.9(3) . . . . ?
C4 C5 C11 N1 -172.35(17) . . . . ?
C6 C5 C11 N1 5.9(3) . . . . ?
C4 C5 C11 C1 4.0(3) . . . . ?
C6 C5 C11 C1 -177.78(18) . . . . ?
C2 C1 C11 C5 24.2(3) . . . . ?
C2 C1 C11 N1 -159.28(17) . . . . ?
C7 C6 C14 C15 -138.56(18) . . . . ?
C5 C6 C14 C15 98.5(2) . . . . ?
C7 C6 C14 C19 41.1(2) . . . . ?
C5 C6 C14 C19 -81.9(2) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C6 C14 C15 C16 179.48(17) . . . . ?
C14 C15 C16 O3 178.99(18) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
O3 C16 C17 C18 -178.9(2) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C14 -1.1(4) . . . . ?
C15 C14 C19 C18 1.2(3) . . . . ?
C6 C14 C19 C18 -178.43(19) . . . . ?
C5 C11 N1 C10 8.6(3) . . . . ?
C1 C11 N1 C10 -168.05(17) . . . . ?
N2 C10 N1 C11 171.32(16) . . . . ?
C7 C10 N1 C11 -8.6(3) . . . . ?
N3 C9 N2 C10 3.3(3) . . . . ?
O1 C9 N2 C10 -176.97(16) . . . . ?
N1 C10 N2 C9 178.57(16) . . . . ?
C7 C10 N2 C9 -1.6(3) . . . . ?
O2 C8 N3 C9 -178.54(16) . . . . ?
C7 C8 N3 C9 -0.3(3) . . . . ?
N2 C9 N3 C8 -2.4(3) . . . . ?
O1 C9 N3 C8 177.83(15) . . . . ?
N2 C9 O1 C21 0.7(3) . . . . ?
N3 C9 O1 C21 -179.50(16) . . . . ?
N3 C8 O2 C20 3.9(3) . . . . ?
C7 C8 O2 C20 -174.51(17) . . . . ?
C17 C16 O3 C22 6.5(3) . . . . ?
C15 C16 O3 C22 -173.46(18) . . . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_104
_database_code_depnum_ccdc_archive 'CCDC 2157099'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar
India
;
_audit_update_record             
;
2022-03-08 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-(3-chlorophenyl)-2,4-dimethoxy-8,8-dimethyl-5,8,9,10-tetrahydropyrimido[4,5-b]quinolin-6(7H)-one
_chemical_name_common            ?
_chemical_melting_point          513-515
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cl N3 O3'
_chemical_formula_weight         399.88

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'
Cl Cl 0.1484 0.1585 '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                   12.2403(6)
_cell_length_b                   13.3075(7)
_cell_length_c                   12.8408(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.168(2)
_cell_angle_gamma                90
_cell_volume                     1975.65(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4626
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.43

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13789
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3472
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.7555P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51611(16) 0.26726(15) 0.56412(15) 0.0350(5) Uani 1 1 d . . . . .
C2 C 0.43670(17) 0.20687(17) 0.60667(17) 0.0448(5) Uani 1 1 d . . . . .
H2A H 0.3832 0.1704 0.5457 0.054 Uiso 1 1 calc R U . . .
H2B H 0.3918 0.2524 0.6355 0.054 Uiso 1 1 calc R U . . .
C3 C 0.49914(17) 0.13205(17) 0.69688(17) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.59842(19) 0.18754(18) 0.78097(17) 0.0483(6) Uani 1 1 d . . . . .
H4A H 0.5661 0.2325 0.8227 0.058 Uiso 1 1 calc R U . . .
H4B H 0.6457 0.1386 0.8322 0.058 Uiso 1 1 calc R U . . .
C5 C 0.67550(16) 0.24776(15) 0.73448(15) 0.0361(5) Uani 1 1 d . . . . .
C6 C 0.62891(16) 0.28445(15) 0.62258(15) 0.0334(4) Uani 1 1 d . . . . .
C7 C 0.70814(15) 0.34290(15) 0.57504(15) 0.0337(5) Uani 1 1 d . . . . .
H7 H 0.7557 0.3882 0.6323 0.040 Uiso 1 1 calc R U . . .
C8 C 0.63602(16) 0.40594(15) 0.47912(15) 0.0336(4) Uani 1 1 d . . . . .
C9 C 0.67933(16) 0.48521(15) 0.43369(16) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.50989(17) 0.50349(15) 0.29826(15) 0.0368(5) Uani 1 1 d . . . . .
C11 C 0.52132(16) 0.38441(15) 0.42438(15) 0.0339(4) Uani 1 1 d . . . . .
C12 C 0.5451(2) 0.0443(2) 0.6473(2) 0.0696(8) Uani 1 1 d . . . . .
H12A H 0.4816 0.0089 0.5962 0.104 Uiso 1 1 calc R U . . .
H12B H 0.5875 -0.0005 0.7050 0.104 Uiso 1 1 calc R U . . .
H12C H 0.5954 0.0692 0.6094 0.104 Uiso 1 1 calc R U . . .
C13 C 0.4159(2) 0.0919(2) 0.7533(2) 0.0700(8) Uani 1 1 d . . . . .
H13A H 0.3516 0.0596 0.6997 0.105 Uiso 1 1 calc R U . . .
H13B H 0.3882 0.1466 0.7865 0.105 Uiso 1 1 calc R U . . .
H13C H 0.4554 0.0444 0.8092 0.105 Uiso 1 1 calc R U . . .
C14 C 0.78880(16) 0.27233(15) 0.54061(15) 0.0348(5) Uani 1 1 d . . . . .
C15 C 0.90255(16) 0.25908(16) 0.60747(17) 0.0397(5) Uani 1 1 d . . . . .
H15 H 0.9307 0.2933 0.6741 0.048 Uiso 1 1 calc R U . . .
C16 C 0.97392(18) 0.19504(17) 0.57494(19) 0.0454(5) Uani 1 1 d . . . . .
C17 C 0.9356(2) 0.1445(2) 0.4769(2) 0.0605(7) Uani 1 1 d . . . . .
H17 H 0.9851 0.1024 0.4555 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8230(2) 0.1569(2) 0.4106(2) 0.0662(7) Uani 1 1 d . . . . .
H18 H 0.7959 0.1228 0.3438 0.079 Uiso 1 1 calc R U . . .
C19 C 0.7496(2) 0.21961(18) 0.44228(18) 0.0515(6) Uani 1 1 d . . . . .
H19 H 0.6731 0.2265 0.3971 0.062 Uiso 1 1 calc R U . . .
C20 C 0.83748(19) 0.59100(18) 0.43860(18) 0.0514(6) Uani 1 1 d . . . . .
H20A H 0.8232 0.5785 0.3616 0.077 Uiso 1 1 calc R U . . .
H20B H 0.9193 0.5957 0.4759 0.077 Uiso 1 1 calc R U . . .
H20C H 0.8011 0.6529 0.4473 0.077 Uiso 1 1 calc R U . . .
C21 C 0.33567(18) 0.52271(18) 0.14861(18) 0.0500(6) Uani 1 1 d . . . . .
H21A H 0.3338 0.4521 0.1327 0.075 Uiso 1 1 calc R U . . .
H21B H 0.3056 0.5597 0.0810 0.075 Uiso 1 1 calc R U . . .
H21C H 0.2894 0.5360 0.1946 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 1.11582(5) 0.17668(6) 0.66145(6) 0.0710(2) Uani 1 1 d . . . . .
N1 N 0.46622(13) 0.31031(13) 0.46254(13) 0.0401(4) Uani 1 1 d . . . . .
H1 H 0.3989 0.2904 0.4218 0.048 Uiso 1 1 calc R U . . .
N2 N 0.61888(14) 0.53561(13) 0.34387(13) 0.0397(4) Uani 1 1 d . . . . .
N3 N 0.45547(13) 0.43248(13) 0.33257(12) 0.0372(4) Uani 1 1 d . . . . .
O1 O 0.77485(11) 0.26856(11) 0.79309(11) 0.0440(4) Uani 1 1 d . . . . .
O2 O 0.79088(11) 0.50989(11) 0.48494(11) 0.0456(4) Uani 1 1 d . . . . .
O3 O 0.45267(12) 0.55309(11) 0.20470(11) 0.0462(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 C6 1.357(3) . ?
C1 N1 1.371(2) . ?
C1 C2 1.496(3) . ?
C2 C3 1.528(3) . ?
C3 C12 1.524(3) . ?
C3 C4 1.525(3) . ?
C3 C13 1.528(3) . ?
C4 C5 1.503(3) . ?
C5 O1 1.233(2) . ?
C5 C6 1.446(3) . ?
C6 C7 1.519(3) . ?
C7 C8 1.512(3) . ?
C7 C14 1.529(3) . ?
C8 C11 1.378(3) . ?
C8 C9 1.392(3) . ?
C9 N2 1.329(2) . ?
C9 O2 1.347(2) . ?
C10 N3 1.313(3) . ?
C10 N2 1.339(3) . ?
C10 O3 1.348(2) . ?
C11 N3 1.351(2) . ?
C11 N1 1.373(2) . ?
C14 C19 1.385(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.367(3) . ?
C16 Cl1 1.745(2) . ?
C17 C18 1.371(3) . ?
C18 C19 1.382(3) . ?
C20 O2 1.438(2) . ?
C21 O3 1.434(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
C6 C1 N1 120.69(17) . . ?
C6 C1 C2 123.61(17) . . ?
N1 C1 C2 115.60(16) . . ?
C1 C2 C3 113.80(16) . . ?
C12 C3 C4 110.43(19) . . ?
C12 C3 C13 109.0(2) . . ?
C4 C3 C13 109.52(19) . . ?
C12 C3 C2 110.12(19) . . ?
C4 C3 C2 107.76(18) . . ?
C13 C3 C2 109.97(18) . . ?
C5 C4 C3 115.79(17) . . ?
O1 C5 C6 121.26(18) . . ?
O1 C5 C4 119.94(17) . . ?
C6 C5 C4 118.73(17) . . ?
C1 C6 C5 119.37(17) . . ?
C1 C6 C7 122.14(16) . . ?
C5 C6 C7 118.48(16) . . ?
C8 C7 C6 109.42(15) . . ?
C8 C7 C14 111.40(15) . . ?
C6 C7 C14 111.08(16) . . ?
C11 C8 C9 114.09(17) . . ?
C11 C8 C7 121.65(17) . . ?
C9 C8 C7 124.13(16) . . ?
N2 C9 O2 119.14(17) . . ?
N2 C9 C8 124.47(18) . . ?
O2 C9 C8 116.38(17) . . ?
N3 C10 N2 128.72(17) . . ?
N3 C10 O3 118.62(17) . . ?
N2 C10 O3 112.66(17) . . ?
N3 C11 N1 115.42(16) . . ?
N3 C11 C8 124.25(18) . . ?
N1 C11 C8 120.33(17) . . ?
C19 C14 C15 118.48(19) . . ?
C19 C14 C7 120.75(17) . . ?
C15 C14 C7 120.77(17) . . ?
C16 C15 C14 119.9(2) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 Cl1 119.10(18) . . ?
C15 C16 Cl1 119.39(18) . . ?
C16 C17 C18 118.9(2) . . ?
C17 C18 C19 120.5(2) . . ?
C18 C19 C14 120.7(2) . . ?
C1 N1 C11 121.48(16) . . ?
C9 N2 C10 114.16(17) . . ?
C10 N3 C11 114.24(16) . . ?
C9 O2 C20 117.19(16) . . ?
C10 O3 C21 116.79(16) . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_102
_database_code_depnum_ccdc_archive 'CCDC 2149722'
loop_
_audit_author_name
_audit_author_address
'Hitendra M. Patel'
;Department of Chemistry,Sardar Patel University
India
;
_audit_update_record             
;
2022-02-02 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
2,4-dimethoxy-8,8-dimethyl-5-phenyl-5,8,9,10-tetrahydropyrimido[4,5-b]quinolin-6(7H)-one
_chemical_name_common            ?
_chemical_melting_point          517-519
_chemical_formula_moiety         'C21 H23 N3 O3'
_chemical_formula_sum            'C21 H23 N3 O3'
_chemical_formula_weight         365.42

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                   11.3367(6)
_cell_length_b                   13.5799(7)
_cell_length_c                   13.0546(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.872(2)
_cell_angle_gamma                90
_cell_volume                     1901.73(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5580
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.13

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15821
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.073
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3353
_reflns_number_gt                2604
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0088(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.556
_refine_ls_restrained_S_all      1.556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99751(13) 0.77477(11) 0.94178(10) 0.0360(4) Uani 1 1 d . . . . .
C2 C 1.08955(14) 0.71576(12) 0.90708(12) 0.0458(4) Uani 1 1 d . . . . .
H2A H 1.1441 0.6812 0.9695 0.055 Uiso 1 1 calc R U . . .
H2B H 1.1406 0.7605 0.8815 0.055 Uiso 1 1 calc R U . . .
C3 C 1.03029(14) 0.64110(12) 0.81856(11) 0.0437(4) Uani 1 1 d . . . . .
C4 C 0.92778(15) 0.69459(14) 0.73058(11) 0.0523(5) Uani 1 1 d . . . . .
H4A H 0.9670 0.7376 0.6918 0.063 Uiso 1 1 calc R U . . .
H4B H 0.8801 0.6460 0.6794 0.063 Uiso 1 1 calc R U . . .
C5 C 0.83877(14) 0.75480(11) 0.76825(11) 0.0378(4) Uani 1 1 d . . . . .
C6 C 0.87924(13) 0.79213(11) 0.87795(10) 0.0337(4) Uani 1 1 d . . . . .
C7 C 0.78735(12) 0.84995(11) 0.91722(10) 0.0349(4) Uani 1 1 d . . . . .
H7 H 0.7430 0.8960 0.8600 0.042 Uiso 1 1 calc R U . . .
C8 C 0.85770(13) 0.90919(11) 1.01636(10) 0.0342(3) Uani 1 1 d . . . . .
C9 C 0.80560(13) 0.98536(11) 1.05925(11) 0.0372(4) Uani 1 1 d . . . . .
C10 C 0.98013(14) 1.00099(11) 1.20101(10) 0.0376(4) Uani 1 1 d . . . . .
C11 C 0.97904(13) 0.88784(11) 1.07610(10) 0.0347(4) Uani 1 1 d . . . . .
C12 C 1.12863(17) 0.60188(16) 0.77188(14) 0.0726(6) Uani 1 1 d . . . . .
H12A H 1.1646 0.6558 0.7447 0.109 Uiso 1 1 calc R U . . .
H12B H 1.0903 0.5568 0.7140 0.109 Uiso 1 1 calc R U . . .
H12C H 1.1927 0.5684 0.8276 0.109 Uiso 1 1 calc R U . . .
C13 C 0.97582(19) 0.55580(15) 0.86384(17) 0.0763(6) Uani 1 1 d . . . . .
H13A H 1.0418 0.5208 0.9162 0.114 Uiso 1 1 calc R U . . .
H13B H 0.9329 0.5120 0.8061 0.114 Uiso 1 1 calc R U . . .
H13C H 0.9184 0.5807 0.8978 0.114 Uiso 1 1 calc R U . . .
C14 C 0.69098(14) 0.78171(12) 0.93977(12) 0.0415(4) Uani 1 1 d . . . . .
C15 C 0.57508(15) 0.76868(13) 0.86354(15) 0.0567(5) Uani 1 1 d . . . . .
H15 H 0.5546 0.8025 0.7982 0.068 Uiso 1 1 calc R U . . .
C16 C 0.48859(18) 0.70549(17) 0.8835(2) 0.0791(7) Uani 1 1 d . . . . .
H16 H 0.4108 0.6971 0.8314 0.095 Uiso 1 1 calc R U . . .
C17 C 0.5173(2) 0.65548(17) 0.9794(2) 0.0886(8) Uani 1 1 d . . . . .
H17 H 0.4591 0.6134 0.9927 0.106 Uiso 1 1 calc R U . . .
C18 C 0.6316(2) 0.66770(16) 1.05553(18) 0.0805(7) Uani 1 1 d . . . . .
H18 H 0.6512 0.6343 1.1211 0.097 Uiso 1 1 calc R U . . .
C19 C 0.71859(18) 0.72971(13) 1.03552(14) 0.0599(5) Uani 1 1 d . . . . .
H19 H 0.7968 0.7364 1.0874 0.072 Uiso 1 1 calc R U . . .
C20 C 0.63169(15) 1.08931(12) 1.04481(13) 0.0501(4) Uani 1 1 d . . . . .
H20A H 0.6411 1.0768 1.1194 0.075 Uiso 1 1 calc R U . . .
H20B H 0.5447 1.0937 1.0038 0.075 Uiso 1 1 calc R U . . .
H20C H 0.6722 1.1501 1.0390 0.075 Uiso 1 1 calc R U . . .
C21 C 1.16068(14) 1.01863(13) 1.35371(12) 0.0513(4) Uani 1 1 d . . . . .
H21A H 1.1627 0.9493 1.3688 0.077 Uiso 1 1 calc R U . . .
H21B H 1.1897 1.0546 1.4205 0.077 Uiso 1 1 calc R U . . .
H21C H 1.2135 1.0325 1.3110 0.077 Uiso 1 1 calc R U . . .
N1 N 1.04396(12) 0.81660(10) 1.04207(9) 0.0425(3) Uani 1 1 d . . . . .
N2 N 0.86372(12) 1.03221(9) 1.15084(9) 0.0412(3) Uani 1 1 d . . . . .
N3 N 1.04368(11) 0.93331(9) 1.16950(8) 0.0388(3) Uani 1 1 d . . . . .
O1 O 0.73524(9) 0.77504(8) 0.70436(7) 0.0470(3) Uani 1 1 d . . . . .
O2 O 0.68724(9) 1.01034(8) 1.00323(8) 0.0475(3) Uani 1 1 d . . . . .
O3 O 1.03546(10) 1.04774(8) 1.29520(7) 0.0485(3) Uani 1 1 d . . . . .
H1N H 1.1174(15) 0.7984(12) 1.0893(12) 0.053(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3509(19) . ?
C1 N1 1.3668(17) . ?
C1 C2 1.497(2) . ?
C2 C3 1.521(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C13 1.519(2) . ?
C3 C4 1.528(2) . ?
C3 C12 1.529(2) . ?
C4 C5 1.500(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.2310(16) . ?
C5 C6 1.4468(19) . ?
C6 C7 1.5199(19) . ?
C7 C8 1.5135(18) . ?
C7 C14 1.532(2) . ?
C7 H7 0.9800 . ?
C8 C11 1.3749(18) . ?
C8 C9 1.395(2) . ?
C9 N2 1.3262(18) . ?
C9 O2 1.3474(16) . ?
C10 N3 1.3133(18) . ?
C10 N2 1.3384(18) . ?
C10 O3 1.3452(16) . ?
C11 N3 1.3517(17) . ?
C11 N1 1.3735(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.379(2) . ?
C14 C19 1.381(2) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.4361(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.4330(17) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1N 0.896(16) . ?

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
C6 C1 N1 121.09(13) . . ?
C6 C1 C2 123.82(12) . . ?
N1 C1 C2 114.96(12) . . ?
C1 C2 C3 114.02(12) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C13 C3 C2 110.36(13) . . ?
C13 C3 C4 110.42(14) . . ?
C2 C3 C4 107.21(13) . . ?
C13 C3 C12 109.27(16) . . ?
C2 C3 C12 109.60(14) . . ?
C4 C3 C12 109.96(13) . . ?
C5 C4 C3 116.20(12) . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
O1 C5 C6 121.33(14) . . ?
O1 C5 C4 119.65(12) . . ?
C6 C5 C4 118.95(13) . . ?
C1 C6 C5 118.89(13) . . ?
C1 C6 C7 122.27(11) . . ?
C5 C6 C7 118.84(12) . . ?
C8 C7 C6 109.51(11) . . ?
C8 C7 C14 111.62(11) . . ?
C6 C7 C14 111.19(12) . . ?
C8 C7 H7 108.1 . . ?
C6 C7 H7 108.1 . . ?
C14 C7 H7 108.1 . . ?
C11 C8 C9 113.86(12) . . ?
C11 C8 C7 121.79(13) . . ?
C9 C8 C7 124.25(13) . . ?
N2 C9 O2 119.06(13) . . ?
N2 C9 C8 124.48(13) . . ?
O2 C9 C8 116.45(12) . . ?
N3 C10 N2 128.49(13) . . ?
N3 C10 O3 118.41(13) . . ?
N2 C10 O3 113.10(13) . . ?
N3 C11 N1 115.00(12) . . ?
N3 C11 C8 124.50(13) . . ?
N1 C11 C8 120.50(12) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.15(16) . . ?
C15 C14 C7 120.74(14) . . ?
C19 C14 C7 121.09(14) . . ?
C14 C15 C16 120.61(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 121.01(19) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C11 121.45(12) . . ?
C1 N1 H1N 122.0(10) . . ?
C11 N1 H1N 116.6(10) . . ?
C9 N2 C10 114.39(13) . . ?
C10 N3 C11 114.20(13) . . ?
C9 O2 C20 117.66(12) . . ?
C10 O3 C21 116.46(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -25.5(2) . . . . ?
N1 C1 C2 C3 158.77(13) . . . . ?
C1 C2 C3 C13 -72.19(18) . . . . ?
C1 C2 C3 C4 48.11(18) . . . . ?
C1 C2 C3 C12 167.43(14) . . . . ?
C13 C3 C4 C5 71.47(19) . . . . ?
C2 C3 C4 C5 -48.79(19) . . . . ?
C12 C3 C4 C5 -167.87(15) . . . . ?
C3 C4 C5 O1 -158.16(14) . . . . ?
C3 C4 C5 C6 25.0(2) . . . . ?
N1 C1 C6 C5 173.43(13) . . . . ?
C2 C1 C6 C5 -2.1(2) . . . . ?
N1 C1 C6 C7 -6.3(2) . . . . ?
C2 C1 C6 C7 178.19(14) . . . . ?
O1 C5 C6 C1 -174.33(14) . . . . ?
C4 C5 C6 C1 2.5(2) . . . . ?
O1 C5 C6 C7 5.4(2) . . . . ?
C4 C5 C6 C7 -177.79(13) . . . . ?
C1 C6 C7 C8 18.37(19) . . . . ?
C5 C6 C7 C8 -161.34(12) . . . . ?
C1 C6 C7 C14 -105.46(15) . . . . ?
C5 C6 C7 C14 74.83(16) . . . . ?
C6 C7 C8 C11 -17.85(18) . . . . ?
C14 C7 C8 C11 105.73(15) . . . . ?
C6 C7 C8 C9 165.95(13) . . . . ?
C14 C7 C8 C9 -70.47(18) . . . . ?
C11 C8 C9 N2 -2.1(2) . . . . ?
C7 C8 C9 N2 174.34(13) . . . . ?
C11 C8 C9 O2 179.16(12) . . . . ?
C7 C8 C9 O2 -4.4(2) . . . . ?
C9 C8 C11 N3 1.6(2) . . . . ?
C7 C8 C11 N3 -175.01(13) . . . . ?
C9 C8 C11 N1 -177.95(13) . . . . ?
C7 C8 C11 N1 5.5(2) . . . . ?
C8 C7 C14 C15 140.04(14) . . . . ?
C6 C7 C14 C15 -97.34(16) . . . . ?
C8 C7 C14 C19 -41.62(19) . . . . ?
C6 C7 C14 C19 81.00(17) . . . . ?
C19 C14 C15 C16 0.5(2) . . . . ?
C7 C14 C15 C16 178.94(15) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C14 1.3(3) . . . . ?
C15 C14 C19 C18 -1.3(2) . . . . ?
C7 C14 C19 C18 -179.67(15) . . . . ?
C6 C1 N1 C11 -9.0(2) . . . . ?
C2 C1 N1 C11 166.94(14) . . . . ?
N3 C11 N1 C1 -170.23(12) . . . . ?
C8 C11 N1 C1 9.3(2) . . . . ?
O2 C9 N2 C10 179.08(12) . . . . ?
C8 C9 N2 C10 0.4(2) . . . . ?
N3 C10 N2 C9 2.4(2) . . . . ?
O3 C10 N2 C9 -178.14(12) . . . . ?
N2 C10 N3 C11 -2.9(2) . . . . ?
O3 C10 N3 C11 177.67(12) . . . . ?
N1 C11 N3 C10 -179.81(12) . . . . ?
C8 C11 N3 C10 0.7(2) . . . . ?
N2 C9 O2 C20 1.9(2) . . . . ?
C8 C9 O2 C20 -179.29(13) . . . . ?
N3 C10 O3 C21 -0.2(2) . . . . ?
N2 C10 O3 C21 -179.79(12) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034


# start Validation Reply Form
_vrf_PLAT230_102                 
;
PROBLEM: Hirshfeld Test Diff for    C3       --C4       .        8.3 s.u.  
RESPONSE:This alarm is due to the elongated ADPs of carbon 
atoms which suggest that these are probably disordered.  
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane:methanol (10:1)'
