# 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. 
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data_v487_fin
_database_code_depnum_ccdc_archive 'CCDC 1015263'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
N1-(2-carboxyphenyl)-N2-(4-bromophenyl)oxalamide
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H22 Br2 N4 O8'
_chemical_formula_sum            'C30 H22 Br2 N4 O8'
_chemical_melting_point          ?

_exptl_crystal_description       prisn
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         726.34

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'
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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.555(3)
_cell_length_b                   11.210(3)
_cell_length_c                   15.335(4)
_cell_angle_alpha                108.324(3)
_cell_angle_beta                 97.068(4)
_cell_angle_gamma                105.848(4)
_cell_volume                     1460.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7067
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.93
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4835
_exptl_absorpt_correction_T_max  0.6010
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              SmartApexII
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23079
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5742
_reflns_number_gt                4286
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)²+0.4563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5742
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_restrained_S_all      0.880
_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
Br1A Br 1.10421(4) 1.26286(3) 1.41834(2) 0.07093(16) Uani 1 1 d . . .
O19A O -0.0786(2) 0.4324(2) 0.87342(18) 0.0545(5) Uani 1 1 d . . .
O18A O 0.1297(2) 0.5883(2) 0.96772(15) 0.0621(6) Uani 1 1 d . . .
C27B C 0.4346(4) 0.6780(3) 0.2446(2) 0.0624(8) Uani 1 1 d . . .
H27B H 0.4436 0.7239 0.2034 0.075 Uiso 1 1 calc R . .
C26B C 0.4560(4) 0.7464(4) 0.3404(2) 0.0702(9) Uani 1 1 d . . .
H26B H 0.4802 0.8386 0.3639 0.084 Uiso 1 1 calc R . .
Br1B Br 0.46532(6) 0.77059(6) 0.53203(3) 0.1127(2) Uani 1 1 d . . .
O18B O -0.1469(2) 0.0834(2) -0.09627(13) 0.0552(5) Uani 1 1 d . . .
N11A N 0.3325(3) 0.7019(2) 0.89053(17) 0.0468(5) Uani 1 1 d . . .
O19B O -0.3185(3) -0.0143(3) -0.23113(17) 0.0865(9) Uani 1 1 d . . .
N11B N 0.1203(3) 0.2407(2) -0.09979(16) 0.0431(5) Uani 1 1 d . . .
C18A C 0.0500(3) 0.5241(3) 0.8883(2) 0.0448(6) Uani 1 1 d . . .
C13A C 0.0909(3) 0.5393(3) 0.8018(2) 0.0437(6) Uani 1 1 d . . .
C12A C 0.2313(3) 0.6243(3) 0.80313(19) 0.0429(6) Uani 1 1 d . . .
C1A C 0.4653(3) 0.7958(3) 0.9098(2) 0.0437(6) Uani 1 1 d . . .
C2A C 0.5323(3) 0.8583(3) 1.0161(2) 0.0455(6) Uani 1 1 d . . .
N21A N 0.6667(3) 0.9523(2) 1.03888(17) 0.0443(5) Uani 1 1 d . . .
C22A C 0.7626(3) 1.0245(2) 1.12939(18) 0.0411(6) Uani 1 1 d . . .
C27A C 0.9036(3) 1.1051(3) 1.1338(2) 0.0478(6) Uani 1 1 d . . .
H27A H 0.9307 1.1112 1.0788 0.057 Uiso 1 1 calc R . .
C26A C 1.0045(3) 1.1766(3) 1.2197(2) 0.0502(7) Uani 1 1 d . . .
H26A H 1.0993 1.2310 1.2226 0.060 Uiso 1 1 calc R . .
C25A C 0.9638(3) 1.1670(3) 1.30079(19) 0.0481(6) Uani 1 1 d . . .
C23A C 0.7225(3) 1.0185(3) 1.2127(2) 0.0520(7) Uani 1 1 d . . .
H23A H 0.6271 0.9661 1.2107 0.062 Uiso 1 1 calc R . .
C24A C 0.8236(4) 1.0900(3) 1.2980(2) 0.0546(7) Uani 1 1 d . . .
H24A H 0.7967 1.0859 1.3536 0.065 Uiso 1 1 calc R . .
O2A O 0.4645(3) 0.8235(3) 1.07128(16) 0.0742(7) Uani 1 1 d . . .
O1A O 0.5293(2) 0.8323(2) 0.85383(15) 0.0602(6) Uani 1 1 d . . .
C14A C -0.0120(3) 0.4657(3) 0.7157(2) 0.0522(7) Uani 1 1 d . . .
H14A H -0.1055 0.4110 0.7145 0.063 Uiso 1 1 calc R . .
C15A C 0.0222(4) 0.4724(3) 0.6325(2) 0.0595(8) Uani 1 1 d . . .
H15A H -0.0480 0.4234 0.5756 0.071 Uiso 1 1 calc R . .
C16A C 0.1606(4) 0.5521(3) 0.6340(2) 0.0612(8) Uani 1 1 d . . .
H16A H 0.1846 0.5548 0.5776 0.073 Uiso 1 1 calc R . .
C17A C 0.2651(3) 0.6284(3) 0.7181(2) 0.0515(7) Uani 1 1 d . . .
H17A H 0.3580 0.6825 0.7178 0.062 Uiso 1 1 calc R . .
C18B C -0.1823(3) 0.0619(3) -0.1802(2) 0.0497(7) Uani 1 1 d . . .
C13B C -0.0836(3) 0.1117(3) -0.23726(18) 0.0435(6) Uani 1 1 d . . .
C12B C 0.0656(3) 0.1956(2) -0.19763(18) 0.0407(6) Uani 1 1 d . . .
C1B C 0.2496(3) 0.3335(3) -0.0473(2) 0.0467(6) Uani 1 1 d . . .
C2B C 0.2609(3) 0.3651(3) 0.0588(2) 0.0461(6) Uani 1 1 d . . .
N21B N 0.3749(3) 0.4742(3) 0.11202(19) 0.0569(7) Uani 1 1 d . . .
C22B C 0.3996(3) 0.5410(3) 0.2105(2) 0.0521(7) Uani 1 1 d . . .
C25B C 0.4413(4) 0.6772(4) 0.4004(2) 0.0691(10) Uani 1 1 d . . .
C23B C 0.3877(4) 0.4728(4) 0.2717(2) 0.0618(8) Uani 1 1 d . . .
H23B H 0.3658 0.3810 0.2488 0.074 Uiso 1 1 calc R . .
O1B O 0.3494(3) 0.3923(3) -0.07608(17) 0.0832(8) Uani 1 1 d . . .
C14B C -0.1385(4) 0.0708(3) -0.3352(2) 0.0543(7) Uani 1 1 d . . .
H14B H -0.2376 0.0171 -0.3622 0.065 Uiso 1 1 calc R . .
C15B C -0.0480(4) 0.1090(3) -0.3916(2) 0.0589(8) Uani 1 1 d . . .
H15B H -0.0859 0.0816 -0.4562 0.071 Uiso 1 1 calc R . .
C16B C 0.0973(4) 0.1873(3) -0.3525(2) 0.0590(8) Uani 1 1 d . . .
H16B H 0.1588 0.2111 -0.3911 0.071 Uiso 1 1 calc R . .
C17B C 0.1549(3) 0.2318(3) -0.2564(2) 0.0507(7) Uani 1 1 d . . .
H17B H 0.2539 0.2863 -0.2309 0.061 Uiso 1 1 calc R . .
O2B O 0.1694(3) 0.2966(2) 0.08732(16) 0.0664(6) Uani 1 1 d . . .
C24B C 0.4085(4) 0.5419(4) 0.3673(2) 0.0710(10) Uani 1 1 d . . .
H24B H 0.4002 0.4965 0.4088 0.085 Uiso 1 1 calc R . .
H11B H 0.060(4) 0.207(3) -0.070(2) 0.053(9) Uiso 1 1 d . . .
H21B H 0.426(4) 0.506(3) 0.091(2) 0.052(10) Uiso 1 1 d . . .
H11A H 0.302(4) 0.686(4) 0.940(3) 0.073(11) Uiso 1 1 d . . .
H21A H 0.697(3) 0.967(3) 0.995(2) 0.039(8) Uiso 1 1 d . . .
H19A H -0.085(5) 0.432(4) 0.924(3) 0.079(14) Uiso 1 1 d . . .
H19B H -0.367(6) -0.053(5) -0.199(4) 0.120(18) 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
Br1A C25A 1.898(3) . ?
O19A C18A 1.309(3) . ?
O19A H19A 0.79(4) . ?
O18A C18A 1.225(3) . ?
C27B C22B 1.384(5) . ?
C27B C26B 1.386(5) . ?
C27B H27B 0.9300 . ?
C26B C25B 1.375(5) . ?
C26B H26B 0.9300 . ?
Br1B C25B 1.910(3) . ?
O18B C18B 1.218(3) . ?
N11A C1A 1.337(4) . ?
N11A C12A 1.406(4) . ?
N11A H11A 0.89(4) . ?
O19B C18B 1.325(4) . ?
O19B H19B 0.85(6) . ?
N11B C1B 1.336(4) . ?
N11B C12B 1.402(3) . ?
N11B H11B 0.85(3) . ?
C18A C13A 1.474(4) . ?
C13A C14A 1.394(4) . ?
C13A C12A 1.411(4) . ?
C12A C17A 1.393(4) . ?
C1A O1A 1.222(3) . ?
C1A C2A 1.529(4) . ?
C2A O2A 1.221(3) . ?
C2A N21A 1.343(4) . ?
N21A C22A 1.413(3) . ?
N21A H21A 0.81(3) . ?
C22A C27A 1.382(4) . ?
C22A C23A 1.395(4) . ?
C27A C26A 1.381(4) . ?
C27A H27A 0.9300 . ?
C26A C25A 1.376(4) . ?
C26A H26A 0.9300 . ?
C25A C24A 1.369(4) . ?
C23A C24A 1.376(4) . ?
C23A H23A 0.9300 . ?
C24A H24A 0.9300 . ?
C14A C15A 1.375(5) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.371(5) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.384(4) . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
C18B C13B 1.479(4) . ?
C13B C12B 1.408(4) . ?
C13B C14B 1.408(4) . ?
C12B C17B 1.392(4) . ?
C1B O1B 1.217(3) . ?
C1B C2B 1.536(4) . ?
C2B O2B 1.219(3) . ?
C2B N21B 1.332(4) . ?
N21B C22B 1.415(4) . ?
N21B H21B 0.70(3) . ?
C22B C23B 1.381(5) . ?
C25B C24B 1.369(5) . ?
C23B C24B 1.385(5) . ?
C23B H23B 0.9300 . ?
C14B C15B 1.377(4) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.363(5) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.382(4) . ?
C16B H16B 0.9300 . ?
C17B H17B 0.9300 . ?
C24B H24B 0.9300 . ?

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
C18A O19A H19A 104(3) . . ?
C22B C27B C26B 119.7(3) . . ?
C22B C27B H27B 120.2 . . ?
C26B C27B H27B 120.2 . . ?
C25B C26B C27B 119.5(3) . . ?
C25B C26B H26B 120.2 . . ?
C27B C26B H26B 120.2 . . ?
C1A N11A C12A 129.3(2) . . ?
C1A N11A H11A 116(2) . . ?
C12A N11A H11A 115(2) . . ?
C18B O19B H19B 110(4) . . ?
C1B N11B C12B 128.3(2) . . ?
C1B N11B H11B 117(2) . . ?
C12B N11B H11B 115(2) . . ?
O18A C18A O19A 121.9(3) . . ?
O18A C18A C13A 123.9(2) . . ?
O19A C18A C13A 114.2(2) . . ?
C14A C13A C12A 118.9(3) . . ?
C14A C13A C18A 118.8(2) . . ?
C12A C13A C18A 122.2(2) . . ?
C17A C12A N11A 122.2(3) . . ?
C17A C12A C13A 119.1(3) . . ?
N11A C12A C13A 118.7(2) . . ?
O1A C1A N11A 127.4(3) . . ?
O1A C1A C2A 121.9(2) . . ?
N11A C1A C2A 110.7(2) . . ?
O2A C2A N21A 126.2(3) . . ?
O2A C2A C1A 120.9(2) . . ?
N21A C2A C1A 112.8(2) . . ?
C2A N21A C22A 127.7(2) . . ?
C2A N21A H21A 116(2) . . ?
C22A N21A H21A 117(2) . . ?
C27A C22A C23A 119.2(3) . . ?
C27A C22A N21A 117.0(2) . . ?
C23A C22A N21A 123.7(3) . . ?
C26A C27A C22A 120.3(3) . . ?
C26A C27A H27A 119.9 . . ?
C22A C27A H27A 119.9 . . ?
C25A C26A C27A 119.5(3) . . ?
C25A C26A H26A 120.2 . . ?
C27A C26A H26A 120.2 . . ?
C24A C25A C26A 121.0(3) . . ?
C24A C25A Br1A 119.7(2) . . ?
C26A C25A Br1A 119.3(2) . . ?
C24A C23A C22A 120.1(3) . . ?
C24A C23A H23A 119.9 . . ?
C22A C23A H23A 119.9 . . ?
C25A C24A C23A 119.8(3) . . ?
C25A C24A H24A 120.1 . . ?
C23A C24A H24A 120.1 . . ?
C15A C14A C13A 121.3(3) . . ?
C15A C14A H14A 119.4 . . ?
C13A C14A H14A 119.4 . . ?
C16A C15A C14A 119.4(3) . . ?
C16A C15A H15A 120.3 . . ?
C14A C15A H15A 120.3 . . ?
C15A C16A C17A 121.1(3) . . ?
C15A C16A H16A 119.4 . . ?
C17A C16A H16A 119.4 . . ?
C16A C17A C12A 120.1(3) . . ?
C16A C17A H17A 120.0 . . ?
C12A C17A H17A 120.0 . . ?
O18B C18B O19B 121.5(3) . . ?
O18B C18B C13B 126.0(3) . . ?
O19B C18B C13B 112.5(3) . . ?
C12B C13B C14B 118.5(2) . . ?
C12B C13B C18B 122.3(2) . . ?
C14B C13B C18B 119.2(3) . . ?
C17B C12B N11B 121.7(3) . . ?
C17B C12B C13B 119.2(2) . . ?
N11B C12B C13B 119.1(2) . . ?
O1B C1B N11B 126.5(3) . . ?
O1B C1B C2B 121.1(3) . . ?
N11B C1B C2B 112.4(2) . . ?
O2B C2B N21B 126.2(3) . . ?
O2B C2B C1B 121.0(2) . . ?
N21B C2B C1B 112.8(2) . . ?
C2B N21B C22B 125.8(3) . . ?
C2B N21B H21B 120(3) . . ?
C22B N21B H21B 114(3) . . ?
C23B C22B C27B 120.2(3) . . ?
C23B C22B N21B 121.7(3) . . ?
C27B C22B N21B 118.1(3) . . ?
C24B C25B C26B 121.1(3) . . ?
C24B C25B Br1B 119.3(3) . . ?
C26B C25B Br1B 119.7(3) . . ?
C22B C23B C24B 119.7(3) . . ?
C22B C23B H23B 120.1 . . ?
C24B C23B H23B 120.1 . . ?
C15B C14B C13B 121.1(3) . . ?
C15B C14B H14B 119.5 . . ?
C13B C14B H14B 119.5 . . ?
C16B C15B C14B 119.7(3) . . ?
C16B C15B H15B 120.1 . . ?
C14B C15B H15B 120.1 . . ?
C15B C16B C17B 121.0(3) . . ?
C15B C16B H16B 119.5 . . ?
C17B C16B H16B 119.5 . . ?
C16B C17B C12B 120.4(3) . . ?
C16B C17B H17B 119.8 . . ?
C12B C17B H17B 119.8 . . ?
C25B C24B C23B 119.7(3) . . ?
C25B C24B H24B 120.1 . . ?
C23B C24B H24B 120.1 . . ?

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
C22B C27B C26B C25B -0.4(5) . . . . ?
O18A C18A C13A C14A -176.7(3) . . . . ?
O19A C18A C13A C14A 5.0(4) . . . . ?
O18A C18A C13A C12A 4.2(4) . . . . ?
O19A C18A C13A C12A -174.0(2) . . . . ?
C1A N11A C12A C17A 5.9(5) . . . . ?
C1A N11A C12A C13A -174.2(3) . . . . ?
C14A C13A C12A C17A -2.3(4) . . . . ?
C18A C13A C12A C17A 176.7(3) . . . . ?
C14A C13A C12A N11A 177.8(2) . . . . ?
C18A C13A C12A N11A -3.2(4) . . . . ?
C12A N11A C1A O1A -2.0(5) . . . . ?
C12A N11A C1A C2A 177.2(3) . . . . ?
O1A C1A C2A O2A 177.6(3) . . . . ?
N11A C1A C2A O2A -1.6(4) . . . . ?
O1A C1A C2A N21A -1.5(4) . . . . ?
N11A C1A C2A N21A 179.3(2) . . . . ?
O2A C2A N21A C22A 4.5(5) . . . . ?
C1A C2A N21A C22A -176.4(2) . . . . ?
C2A N21A C22A C27A 172.4(3) . . . . ?
C2A N21A C22A C23A -7.7(5) . . . . ?
C23A C22A C27A C26A 1.4(4) . . . . ?
N21A C22A C27A C26A -178.7(3) . . . . ?
C22A C27A C26A C25A 0.1(5) . . . . ?
C27A C26A C25A C24A -1.6(5) . . . . ?
C27A C26A C25A Br1A 178.8(2) . . . . ?
C27A C22A C23A C24A -1.4(4) . . . . ?
N21A C22A C23A C24A 178.7(3) . . . . ?
C26A C25A C24A C23A 1.5(5) . . . . ?
Br1A C25A C24A C23A -178.9(2) . . . . ?
C22A C23A C24A C25A 0.0(5) . . . . ?
C12A C13A C14A C15A 1.4(4) . . . . ?
C18A C13A C14A C15A -177.7(3) . . . . ?
C13A C14A C15A C16A 0.6(5) . . . . ?
C14A C15A C16A C17A -1.7(5) . . . . ?
C15A C16A C17A C12A 0.7(5) . . . . ?
N11A C12A C17A C16A -178.7(3) . . . . ?
C13A C12A C17A C16A 1.4(4) . . . . ?
O18B C18B C13B C12B -2.2(5) . . . . ?
O19B C18B C13B C12B 179.3(3) . . . . ?
O18B C18B C13B C14B 175.8(3) . . . . ?
O19B C18B C13B C14B -2.7(4) . . . . ?
C1B N11B C12B C17B 9.7(4) . . . . ?
C1B N11B C12B C13B -170.2(3) . . . . ?
C14B C13B C12B C17B -2.0(4) . . . . ?
C18B C13B C12B C17B 176.0(3) . . . . ?
C14B C13B C12B N11B 177.9(2) . . . . ?
C18B C13B C12B N11B -4.1(4) . . . . ?
C12B N11B C1B O1B -4.3(5) . . . . ?
C12B N11B C1B C2B 173.8(2) . . . . ?
O1B C1B C2B O2B -171.7(3) . . . . ?
N11B C1B C2B O2B 10.1(4) . . . . ?
O1B C1B C2B N21B 10.4(4) . . . . ?
N11B C1B C2B N21B -167.8(3) . . . . ?
O2B C2B N21B C22B -9.0(5) . . . . ?
C1B C2B N21B C22B 168.7(3) . . . . ?
C26B C27B C22B C23B -0.7(5) . . . . ?
C26B C27B C22B N21B 178.5(3) . . . . ?
C2B N21B C22B C23B 46.5(5) . . . . ?
C2B N21B C22B C27B -132.7(3) . . . . ?
C27B C26B C25B C24B 1.2(6) . . . . ?
C27B C26B C25B Br1B -178.2(3) . . . . ?
C27B C22B C23B C24B 1.1(5) . . . . ?
N21B C22B C23B C24B -178.1(3) . . . . ?
C12B C13B C14B C15B 1.6(4) . . . . ?
C18B C13B C14B C15B -176.5(3) . . . . ?
C13B C14B C15B C16B 0.2(5) . . . . ?
C14B C15B C16B C17B -1.6(5) . . . . ?
C15B C16B C17B C12B 1.1(5) . . . . ?
N11B C12B C17B C16B -179.1(3) . . . . ?
C13B C12B C17B C16B 0.8(4) . . . . ?
C26B C25B C24B C23B -0.8(6) . . . . ?
Br1B C25B C24B C23B 178.6(3) . . . . ?
C22B C23B C24B C25B -0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_v501_fin
_database_code_depnum_ccdc_archive 'CCDC 1417946'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        N1-(2-carboxyphenyl)-N2-phenyloxalamide
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H12 N2 O4, C2 H4 O2'
_chemical_formula_sum            'C17 H16 N2 O6'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         344.32

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   15.397(15)
_cell_length_b                   4.991(5)
_cell_length_c                   20.26(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.672(13)
_cell_angle_gamma                90.00
_cell_volume                     1543(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1843
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.05
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   Sadabs


_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Smart Apex II'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13178
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.99
_reflns_number_total             3735
_reflns_number_gt                2444
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0711P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3735
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.008
_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 0.09741(8) 0.1320(3) 0.47723(6) 0.0291(3) Uani 1 1 d . . .
O2 O 0.25019(8) -0.1254(3) 0.60455(7) 0.0323(4) Uani 1 1 d . . .
O18 O 0.39352(8) 0.3734(3) 0.58479(7) 0.0354(4) Uani 1 1 d . . .
N11 N 0.24111(10) 0.2502(3) 0.51385(8) 0.0236(4) Uani 1 1 d . . .
N21 N 0.10680(11) -0.2455(3) 0.57479(8) 0.0249(4) Uani 1 1 d . . .
O30 O 0.57156(9) 0.6581(3) 0.66490(7) 0.0378(4) Uani 1 1 d . . .
O19 O 0.46390(9) 0.7337(3) 0.55612(7) 0.0384(4) Uani 1 1 d . . .
C13 C 0.33752(11) 0.6045(4) 0.48517(9) 0.0237(4) Uani 1 1 d . . .
C27 C 0.02292(11) -0.6085(4) 0.61081(9) 0.0260(4) Uani 1 1 d . . .
H27 H -0.0182 -0.5833 0.5720 0.031 Uiso 1 1 calc R . .
C16 C 0.22603(13) 0.7021(4) 0.36847(10) 0.0287(5) Uani 1 1 d . . .
H16 H 0.1882 0.7345 0.3283 0.034 Uiso 1 1 calc R . .
C25 C 0.06813(12) -0.8450(4) 0.71249(10) 0.0292(4) Uani 1 1 d . . .
H25 H 0.0585 -0.9811 0.7435 0.035 Uiso 1 1 calc R . .
C17 C 0.20579(12) 0.5012(4) 0.41074(9) 0.0273(4) Uani 1 1 d . . .
H17 H 0.1544 0.3968 0.3994 0.033 Uiso 1 1 calc R . .
C12 C 0.26026(11) 0.4509(4) 0.46977(9) 0.0235(4) Uani 1 1 d . . .
C22 C 0.09649(11) -0.4470(4) 0.62195(9) 0.0225(4) Uani 1 1 d . . .
C2 C 0.17931(12) -0.1007(4) 0.57029(9) 0.0237(4) Uani 1 1 d . . .
C24 C 0.14125(13) -0.6837(4) 0.72341(10) 0.0312(5) Uani 1 1 d . . .
H24 H 0.1820 -0.7093 0.7624 0.037 Uiso 1 1 calc R . .
C15 C 0.30019(12) 0.8562(4) 0.38367(10) 0.0289(4) Uani 1 1 d . . .
H15 H 0.3131 0.9956 0.3546 0.035 Uiso 1 1 calc R . .
C23 C 0.15647(12) -0.4859(4) 0.67891(9) 0.0306(5) Uani 1 1 d . . .
H23 H 0.2074 -0.3772 0.6870 0.037 Uiso 1 1 calc R . .
C1 C 0.16669(11) 0.1079(4) 0.51422(9) 0.0230(4) Uani 1 1 d . . .
O31 O 0.50617(10) 0.2871(3) 0.69237(8) 0.0419(4) Uani 1 1 d . . .
C14 C 0.35551(12) 0.8057(4) 0.44157(10) 0.0282(4) Uani 1 1 d . . .
H14 H 0.4070 0.9106 0.4519 0.034 Uiso 1 1 calc R . .
C18 C 0.40019(12) 0.5613(4) 0.54626(10) 0.0274(4) Uani 1 1 d . . .
C26 C 0.00904(12) -0.8056(4) 0.65575(10) 0.0289(5) Uani 1 1 d . . .
H26 H -0.0416 -0.9155 0.6477 0.035 Uiso 1 1 calc R . .
C30 C 0.56739(13) 0.4674(5) 0.70233(10) 0.0343(5) Uani 1 1 d . . .
C31 C 0.63231(14) 0.4178(6) 0.76197(11) 0.0486(6) Uani 1 1 d . . .
H312 H 0.6687 0.2633 0.7539 0.073 Uiso 1 1 calc R . .
H313 H 0.6016 0.3811 0.8003 0.073 Uiso 1 1 calc R . .
H311 H 0.6696 0.5763 0.7711 0.073 Uiso 1 1 calc R . .
H11 H 0.2840(14) 0.211(4) 0.5492(11) 0.043(6) Uiso 1 1 d . . .
H21 H 0.0629(15) -0.208(5) 0.5463(11) 0.041(7) Uiso 1 1 d . . .
H19 H 0.5046(18) 0.685(5) 0.5988(14) 0.076(9) Uiso 1 1 d . . .
H31 H 0.465(2) 0.332(6) 0.6489(15) 0.088(10) 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
O1 C1 1.225(2) . ?
O2 C2 1.219(2) . ?
O18 C18 1.233(2) . ?
N11 C1 1.349(2) . ?
N11 C12 1.400(3) . ?
N21 C2 1.343(3) . ?
N21 C22 1.411(3) . ?
O30 C30 1.224(3) . ?
O19 C18 1.300(2) . ?
C13 C14 1.389(3) . ?
C13 C12 1.415(3) . ?
C13 C18 1.480(3) . ?
C27 C26 1.376(3) . ?
C27 C22 1.384(3) . ?
C16 C15 1.377(3) . ?
C16 C17 1.381(3) . ?
C25 C24 1.378(3) . ?
C25 C26 1.382(3) . ?
C17 C12 1.389(3) . ?
C22 C23 1.392(3) . ?
C2 C1 1.534(3) . ?
C24 C23 1.378(3) . ?
C15 C14 1.378(3) . ?
O31 C30 1.299(3) . ?
C30 C31 1.483(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N11 C12 129.18(16) . . ?
C2 N21 C22 126.82(17) . . ?
C14 C13 C12 118.97(17) . . ?
C14 C13 C18 118.30(17) . . ?
C12 C13 C18 122.73(17) . . ?
C26 C27 C22 120.28(18) . . ?
C15 C16 C17 121.04(18) . . ?
C24 C25 C26 118.93(18) . . ?
C16 C17 C12 120.33(19) . . ?
C17 C12 N11 121.63(17) . . ?
C17 C12 C13 119.04(17) . . ?
N11 C12 C13 119.32(17) . . ?
C27 C22 C23 119.46(18) . . ?
C27 C22 N21 117.92(17) . . ?
C23 C22 N21 122.61(17) . . ?
O2 C2 N21 126.57(19) . . ?
O2 C2 C1 120.38(17) . . ?
N21 C2 C1 113.03(16) . . ?
C25 C24 C23 121.33(19) . . ?
C16 C15 C14 119.23(18) . . ?
C24 C23 C22 119.39(19) . . ?
O1 C1 N11 128.03(18) . . ?
O1 C1 C2 122.24(17) . . ?
N11 C1 C2 109.73(16) . . ?
C15 C14 C13 121.37(18) . . ?
O18 C18 O19 122.07(18) . . ?
O18 C18 C13 122.69(18) . . ?
O19 C18 C13 115.24(18) . . ?
C27 C26 C25 120.61(18) . . ?
O30 C30 O31 122.63(19) . . ?
O30 C30 C31 123.3(2) . . ?
O31 C30 C31 114.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.054

