# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_332
_database_code_depnum_ccdc_archive 'CCDC 1495313'
_audit_update_record             
;
2016-07-22 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXTL
_chemical_name_systematic        
'Methyl 5-(2-methoxybenzoyl)-1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          440
_chemical_formula_moiety         'C16 H15 N O5'
_chemical_formula_sum            'C16 H15 N O5'
_chemical_formula_weight         301.29

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.3195(4)
_cell_length_b                   13.6469(6)
_cell_length_c                   12.8427(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1458.10(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.53

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46442
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.89
_reflns_number_total             2807
_reflns_number_gt                2211
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+1.4524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2807
_refine_ls_number_parameters     202
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.276
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9294(3) 1.00425(18) 0.87068(17) 0.0567(6) Uani 1 1 d . . .
C1 C 0.8280(3) 0.9437(2) 0.8493(2) 0.0404(7) Uani 1 1 d . . .
C2 C 0.8205(4) 0.9015(3) 0.7417(2) 0.0517(8) Uani 1 1 d . . .
C3 C 0.8944(4) 0.8121(3) 0.7210(3) 0.0655(11) Uani 1 1 d . . .
C4 C 0.8970(6) 0.7743(4) 0.6201(4) 0.0990(19) Uani 1 1 d . . .
H4 H 0.9486 0.7147 0.6051 0.119 Uiso 1 1 calc R . .
C5 C 0.8216(7) 0.8271(5) 0.5439(4) 0.1007(16) Uani 1 1 d U . .
H5 H 0.8238 0.8026 0.4755 0.121 Uiso 1 1 calc R . .
C6 C 0.7440(7) 0.9129(5) 0.5616(4) 0.0971(15) Uani 1 1 d U . .
H6 H 0.6906 0.9453 0.5070 0.116 Uiso 1 1 calc R . .
C7 C 0.7443(5) 0.9533(4) 0.6630(3) 0.0793(14) Uani 1 1 d . . .
H7 H 0.6941 1.0136 0.6767 0.095 Uiso 1 1 calc R . .
O2 O 0.9630(3) 0.7677(2) 0.8049(2) 0.0702(8) Uani 1 1 d . . .
C8 C 1.0296(5) 0.6718(3) 0.7907(5) 0.0939(18) Uani 1 1 d . . .
H8A H 0.9493 0.6291 0.7601 0.141 Uiso 1 1 calc R . .
H8B H 1.0627 0.6456 0.8576 0.141 Uiso 1 1 calc R . .
H8C H 1.1220 0.6757 0.7448 0.141 Uiso 1 1 calc R . .
C9 C 0.7091(3) 0.9110(2) 0.9267(2) 0.0369(6) Uani 1 1 d . . .
C10 C 0.5914(3) 0.8451(2) 0.9030(2) 0.0400(7) Uani 1 1 d . . .
H10 H 0.5859 0.8198 0.8350 0.048 Uiso 1 1 calc R . .
N1 N 0.4828(3) 0.81501(18) 0.97403(19) 0.0431(6) Uani 1 1 d . . .
C11 C 0.4848(4) 0.8456(2) 1.0791(2) 0.0450(7) Uani 1 1 d . . .
C12 C 0.6102(3) 0.9151(2) 1.1036(2) 0.0386(6) Uani 1 1 d . . .
C13 C 0.7153(3) 0.9466(2) 1.0295(2) 0.0377(6) Uani 1 1 d . . .
H13 H 0.7938 0.9932 1.0475 0.045 Uiso 1 1 calc R . .
C14 C 0.3539(5) 0.7483(3) 0.9426(3) 0.0646(10) Uani 1 1 d . . .
H14A H 0.3670 0.7313 0.8698 0.097 Uiso 1 1 calc R . .
H14B H 0.2508 0.7802 0.9525 0.097 Uiso 1 1 calc R . .
H14C H 0.3585 0.6894 0.9846 0.097 Uiso 1 1 calc R . .
O3 O 0.3827(3) 0.8144(2) 1.1388(2) 0.0696(8) Uani 1 1 d . . .
C15 C 0.6291(4) 0.9476(2) 1.2132(2) 0.0441(7) Uani 1 1 d . . .
O4 O 0.6062(4) 0.89810(19) 1.28922(18) 0.0662(7) Uani 1 1 d . . .
O5 O 0.6809(3) 1.03991(16) 1.21668(16) 0.0506(6) Uani 1 1 d . . .
C16 C 0.7185(5) 1.0782(3) 1.3184(3) 0.0644(10) Uani 1 1 d . . .
H16A H 0.6271 1.0691 1.3642 0.097 Uiso 1 1 calc R . .
H16B H 0.7431 1.1475 1.3129 0.097 Uiso 1 1 calc R . .
H16C H 0.8108 1.0437 1.3465 0.097 Uiso 1 1 calc R . .


_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 1.212(4) . ?
C1 C9 1.471(4) . ?
C1 C2 1.499(4) . ?
C2 C7 1.387(5) . ?
C2 C3 1.392(6) . ?
C3 O2 1.362(5) . ?
C3 C4 1.394(5) . ?
C4 C5 1.368(8) . ?
C4 H4 0.9400 . ?
C5 C6 1.357(8) . ?
C5 H5 0.9400 . ?
C6 C7 1.413(7) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
O2 C8 1.432(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 C10 1.365(4) . ?
C9 C13 1.408(4) . ?
C10 N1 1.348(4) . ?
C10 H10 0.9400 . ?
N1 C11 1.413(4) . ?
N1 C14 1.463(4) . ?
C11 O3 1.221(4) . ?
C11 C12 1.444(4) . ?
C12 C13 1.362(4) . ?
C12 C15 1.485(4) . ?
C13 H13 0.9400 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 O4 1.202(4) . ?
C15 O5 1.332(4) . ?
O5 C16 1.441(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C9 121.4(3) . . ?
O1 C1 C2 120.0(3) . . ?
C9 C1 C2 118.6(3) . . ?
C7 C2 C3 120.6(4) . . ?
C7 C2 C1 119.7(4) . . ?
C3 C2 C1 119.7(3) . . ?
O2 C3 C2 115.1(3) . . ?
O2 C3 C4 124.4(5) . . ?
C2 C3 C4 120.6(5) . . ?
C5 C4 C3 117.6(6) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C6 C5 C4 123.6(5) . . ?
C6 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 118.3(5) . . ?
C2 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C3 O2 C8 117.9(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C13 117.6(3) . . ?
C10 C9 C1 122.1(3) . . ?
C13 C9 C1 120.3(3) . . ?
N1 C10 C9 122.0(3) . . ?
N1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 N1 C11 123.3(3) . . ?
C10 N1 C14 119.6(3) . . ?
C11 N1 C14 117.2(3) . . ?
O3 C11 N1 119.3(3) . . ?
O3 C11 C12 126.5(3) . . ?
N1 C11 C12 114.2(2) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 C15 120.0(3) . . ?
C11 C12 C15 118.6(3) . . ?
C12 C13 C9 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
C9 C13 H13 119.3 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O5 123.7(3) . . ?
O4 C15 C12 125.8(3) . . ?
O5 C15 C12 110.4(2) . . ?
C15 O5 C16 116.3(3) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 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 C7 -81.4(4) . . . . ?
C9 C1 C2 C7 97.8(4) . . . . ?
O1 C1 C2 C3 96.5(4) . . . . ?
C9 C1 C2 C3 -84.3(4) . . . . ?
C7 C2 C3 O2 -179.1(3) . . . . ?
C1 C2 C3 O2 3.0(4) . . . . ?
C7 C2 C3 C4 1.7(5) . . . . ?
C1 C2 C3 C4 -176.2(3) . . . . ?
O2 C3 C4 C5 179.5(4) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C7 2.4(7) . . . . ?
C3 C2 C7 C6 -0.1(5) . . . . ?
C1 C2 C7 C6 177.9(3) . . . . ?
C5 C6 C7 C2 -1.9(6) . . . . ?
C2 C3 O2 C8 175.0(3) . . . . ?
C4 C3 O2 C8 -5.9(5) . . . . ?
O1 C1 C9 C10 178.1(3) . . . . ?
C2 C1 C9 C10 -1.1(4) . . . . ?
O1 C1 C9 C13 -2.8(4) . . . . ?
C2 C1 C9 C13 178.0(3) . . . . ?
C13 C9 C10 N1 0.7(4) . . . . ?
C1 C9 C10 N1 179.8(3) . . . . ?
C9 C10 N1 C11 -2.6(4) . . . . ?
C9 C10 N1 C14 176.6(3) . . . . ?
C10 N1 C11 O3 -179.5(3) . . . . ?
C14 N1 C11 O3 1.3(5) . . . . ?
C10 N1 C11 C12 2.2(4) . . . . ?
C14 N1 C11 C12 -177.0(3) . . . . ?
O3 C11 C12 C13 -178.3(3) . . . . ?
N1 C11 C12 C13 -0.1(4) . . . . ?
O3 C11 C12 C15 5.3(5) . . . . ?
N1 C11 C12 C15 -176.5(3) . . . . ?
C11 C12 C13 C9 -1.7(4) . . . . ?
C15 C12 C13 C9 174.7(3) . . . . ?
C10 C9 C13 C12 1.4(4) . . . . ?
C1 C9 C13 C12 -177.8(3) . . . . ?
C13 C12 C15 O4 -142.0(3) . . . . ?
C11 C12 C15 O4 34.4(5) . . . . ?
C13 C12 C15 O5 35.9(4) . . . . ?
C11 C12 C15 O5 -147.6(3) . . . . ?
O4 C15 O5 C16 3.5(5) . . . . ?
C12 C15 O5 C16 -174.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.89
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/Hexane'
