# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2N
_database_code_depnum_ccdc_archive 'CCDC 1538731'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Isonicotinamide + 3MeO benzoic acid From MeCN'
_chemical_formula_moiety         '2(C8 H8 O3), C6 H6 N2 O'
_chemical_formula_sum            'C22 H22 N2 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         426.41

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.443(8)
_cell_length_b                   12.603(11)
_cell_length_c                   17.396(16)
_cell_angle_alpha                110.90(2)
_cell_angle_beta                 98.50(2)
_cell_angle_gamma                90.185(19)
_cell_volume                     2112.(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3868
_cell_measurement_theta_min      2.5390
_cell_measurement_theta_max      22.8650
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            36421
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         26.92
_diffrn_reflns_theta_full        26.92
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             8786
_reflns_number_gt                4679
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.2070
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.013
_refine_ls_number_reflns         8786
_refine_ls_number_parameters     570
_refine_ls_number_restraints     8
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0972P)²+0.6113P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap


_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O8 0.32410(19) 0.48508(17) 0.30691(14) 0.0559(6) Uani d . . D 1 . .
H H8 0.3967 0.4902 0.334 0.084 Uiso calc U . DR 1 . .
O O59 0.9182(2) 1.01500(17) 0.69394(14) 0.0563(5) Uani d . . D 1 . .
H H59 0.9753 1.0098 0.6653 0.084 Uiso calc U . DR 1 . .
O O38 0.1473(2) 0.36899(17) 0.65930(14) 0.0560(6) Uani d . . D 1 . .
O O28 0.93244(19) 0.40163(16) 0.56692(13) 0.0561(6) Uani d . . . 1 . .
O O88 0.5656(2) 0.13104(17) 0.34116(14) 0.0566(6) Uani d . . D 1 . .
H H88 0.5137 0.1141 0.3665 0.085 Uiso calc U . DR 1 . .
O O58 0.9162(2) 0.82748(17) 0.64109(14) 0.0567(6) Uani d . . . 1 . .
O O78 0.3962(2) 1.09831(16) 0.43320(14) 0.0572(6) Uani d . . . 1 . .
O O9 0.34796(19) 0.67305(17) 0.36092(14) 0.0572(6) Uani d . . . 1 . .
O O39 0.1903(2) 0.55530(18) 0.70850(15) 0.0651(6) Uani d . . . 1 . .
O O89 0.5838(2) -0.05525(18) 0.29223(15) 0.0656(6) Uani d . . . 1 . .
O O90 0.8773(2) -0.12962(18) 0.08675(15) 0.0688(7) Uani d . . . 1 . .
O O40 0.5831(2) 0.63010(18) 0.91658(15) 0.0708(7) Uani d . . . 1 . .
N N73 0.0889(2) 1.0019(2) 0.59321(15) 0.0476(6) Uani d . . . 1 . .
O O10 -0.0631(2) 0.37947(19) 0.09375(16) 0.0771(7) Uani d . . . 1 . .
N N23 0.5442(2) 0.4982(2) 0.40763(15) 0.0476(6) Uani d . . . 1 . .
O O60 0.6415(3) 1.1219(2) 0.90916(16) 0.0809(8) Uani d . . . 1 . .
N N79 0.4038(2) 0.9087(2) 0.38890(16) 0.0564(7) Uani d . . D 1 . .
H H79A 0.4583 0.9072 0.356 0.068 Uiso calc U . DR 1 . .
H H79B 0.3763 0.8463 0.3922 0.068 Uiso calc U . DR 1 . .
N N29 0.9607(2) 0.5914(2) 0.61282(16) 0.0558(7) Uani d . . D 1 . .
H H29A 1.0313 0.5929 0.6457 0.067 Uiso calc U . DR 1 . .
H H29B 0.9313 0.6538 0.6101 0.067 Uiso calc U . DR 1 . .
C C36 0.3331(2) 0.4429(2) 0.76152(17) 0.0406(6) Uani d . . . 1 . .
C C56 0.7956(2) 0.9159(2) 0.75161(17) 0.0425(6) Uani d . . . 1 . .
C C76 0.2646(2) 1.0006(2) 0.49031(16) 0.0418(6) Uani d . . . 1 . .
C C6 0.1723(2) 0.5850(2) 0.25022(17) 0.0422(6) Uani d . . . 1 . .
C C26 0.7717(2) 0.4997(2) 0.51075(16) 0.0399(6) Uani d . . . 1 . .
C C86 0.7013(2) 0.0569(2) 0.23976(17) 0.0422(6) Uani d . . . 1 . .
C C57 0.8826(3) 0.9141(2) 0.69056(18) 0.0450(7) Uani d . . . 1 . .
C C81 0.7513(3) -0.0386(2) 0.18819(18) 0.0464(7) Uani d . . . 1 . .
H H81 0.7295 -0.1098 0.1889 0.056 Uiso calc U . R 1 . .
C C87 0.6114(3) 0.0386(2) 0.29335(18) 0.0462(7) Uani d . . . 1 . .
C C35 0.4082(3) 0.5389(2) 0.81380(18) 0.0463(7) Uani d . . . 1 . .
H H35 0.3863 0.6101 0.8131 0.056 Uiso calc U . R 1 . .
C C77 0.3630(3) 1.0050(2) 0.43344(18) 0.0448(7) Uani d . . . 1 . .
C C34 0.5164(3) 0.5294(2) 0.86747(18) 0.0478(7) Uani d . . . 1 . .
C C27 0.8982(3) 0.4947(2) 0.56722(18) 0.0446(7) Uani d . . . 1 . .
C C82 0.8337(3) -0.0292(2) 0.13535(18) 0.0468(7) Uani d . . . 1 . .
C C7 0.2898(3) 0.5859(2) 0.31126(18) 0.0446(7) Uani d . . . 1 . .
C C37 0.2170(3) 0.4617(2) 0.70757(18) 0.0448(7) Uani d . . . 1 . .
C C1 0.1050(3) 0.4840(2) 0.19842(18) 0.0482(7) Uani d . . . 1 . .
H H1 0.1323 0.4154 0.2017 0.058 Uiso calc U . R 1 . .
C C55 0.7552(3) 1.0171(2) 0.80383(18) 0.0488(7) Uani d . . . 1 . .
H H55 0.7816 1.0857 0.8006 0.059 Uiso calc U . R 1 . .
C C24 0.6054(3) 0.5959(2) 0.45469(19) 0.0485(7) Uani d . . . 1 . .
H H24 0.5715 0.6631 0.4527 0.058 Uiso calc U . R 1 . .
C C22 0.5889(3) 0.4018(2) 0.40885(19) 0.0497(7) Uani d . . . 1 . .
H H22 0.5431 0.3339 0.3748 0.06 Uiso calc U . R 1 . .
C C21 0.7062(3) 0.3987(2) 0.46126(18) 0.0487(7) Uani d . . . 1 . .
H H21 0.7373 0.3299 0.4618 0.058 Uiso calc U . R 1 . .
C C33 0.5506(3) 0.4244(3) 0.8676(2) 0.0538(8) Uani d . . . 1 . .
H H33 0.6235 0.4179 0.9032 0.065 Uiso calc U . R 1 . .
C C31 0.3668(3) 0.3368(2) 0.76131(19) 0.0515(7) Uani d . . . 1 . .
H H31 0.3167 0.2719 0.7258 0.062 Uiso calc U . R 1 . .
C C74 0.1328(3) 1.0981(2) 0.59196(19) 0.0513(7) Uani d . . . 1 . .
H H74 0.1037 1.1658 0.6259 0.062 Uiso calc U . R 1 . .
C C72 0.1256(3) 0.9043(2) 0.54617(19) 0.0488(7) Uani d . . . 1 . .
H H72 0.0916 0.8371 0.5479 0.059 Uiso calc U . R 1 . .
C C2 -0.0033(3) 0.4845(3) 0.14155(19) 0.0524(8) Uani d . . . 1 . .
C C25 0.7238(3) 0.6001(2) 0.50914(19) 0.0512(7) Uani d . . . 1 . .
H H25 0.7672 0.6694 0.5427 0.061 Uiso calc U . R 1 . .
C C83 0.8674(3) 0.0767(3) 0.1347(2) 0.0545(8) Uani d . . . 1 . .
H H83 0.9231 0.0836 0.0995 0.065 Uiso calc U . R 1 . .
C C85 0.7343(3) 0.1635(2) 0.2394(2) 0.0524(7) Uani d . . . 1 . .
H H85 0.7006 0.2281 0.2741 0.063 Uiso calc U . R 1 . .
C C5 0.1307(3) 0.6870(3) 0.2452(2) 0.0547(8) Uani d . . . 1 . .
H H5 0.175 0.7554 0.2799 0.066 Uiso calc U . R 1 . .
C C71 0.2179(3) 0.9001(2) 0.4918(2) 0.0515(7) Uani d . . . 1 . .
H H71 0.2451 0.831 0.4585 0.062 Uiso calc U . R 1 . .
C C75 0.2249(3) 1.1017(2) 0.53956(19) 0.0512(7) Uani d . . . 1 . .
H H75 0.2564 1.1705 0.5391 0.061 Uiso calc U . R 1 . .
C C54 0.6757(3) 1.0168(3) 0.8609(2) 0.0556(8) Uani d . . . 1 . .
C C51 0.7560(3) 0.8138(3) 0.7570(2) 0.0567(8) Uani d . . . 1 . .
H H51 0.783 0.7455 0.7225 0.068 Uiso calc U . R 1 . .
C C32 0.4757(3) 0.3278(3) 0.8144(2) 0.0597(8) Uani d . . . 1 . .
H H32 0.4987 0.2566 0.8144 0.072 Uiso calc U . R 1 . .
C C53 0.6374(3) 0.9146(3) 0.8664(2) 0.0622(9) Uani d . . . 1 . .
H H53 0.5856 0.9136 0.9053 0.075 Uiso calc U . R 1 . .
C C84 0.8171(3) 0.1728(3) 0.1875(2) 0.0589(8) Uani d . . . 1 . .
H H84 0.8399 0.2442 0.1875 0.071 Uiso calc U . R 1 . .
C C3 -0.0441(3) 0.5868(3) 0.1365(2) 0.0591(8) Uani d . . . 1 . .
H H3 -0.1162 0.5878 0.0984 0.071 Uiso calc U . R 1 . .
C C4 0.0231(3) 0.6863(3) 0.1884(2) 0.0642(9) Uani d . . . 1 . .
H H4 -0.0045 0.7549 0.1853 0.077 Uiso calc U . R 1 . .
C C52 0.6773(3) 0.8143(3) 0.8133(2) 0.0663(9) Uani d . . . 1 . .
H H52 0.6499 0.7456 0.8159 0.08 Uiso calc U . R 1 . .
C C91 0.9490(4) -0.1267(3) 0.0241(2) 0.0740(11) Uani d . . . 1 . .
H H91A 0.8972 -0.0973 -0.0133 0.111 Uiso calc U . R 1 . .
H H91B 0.9714 -0.2023 -0.0064 0.111 Uiso calc U . R 1 . .
H H91C 1.0266 -0.0786 0.0496 0.111 Uiso calc U . R 1 . .
C C41 0.6892(3) 0.6272(3) 0.9776(2) 0.0765(11) Uani d . . . 1 . .
H H41A 0.6589 0.5958 1.0149 0.115 Uiso calc U . R 1 . .
H H41B 0.7261 0.7031 1.0085 0.115 Uiso calc U . R 1 . .
H H41C 0.7539 0.5808 0.9504 0.115 Uiso calc U . R 1 . .
C C11 -0.1703(3) 0.3744(3) 0.0312(2) 0.0829(12) Uani d . . . 1 . .
H H11A -0.2373 0.4193 0.0567 0.124 Uiso calc U . R 1 . .
H H11B -0.2033 0.2969 0.0027 0.124 Uiso calc U . R 1 . .
H H11C -0.1425 0.4037 -0.008 0.124 Uiso calc U . R 1 . .
C C61 0.5629(4) 1.1269(4) 0.9706(2) 0.0888(13) Uani d . . . 1 . .
H H61A 0.4838 1.081 0.9442 0.133 Uiso calc U . R 1 . .
H H61B 0.5429 1.2043 0.9981 0.133 Uiso calc U . R 1 . .
H H61C 0.6088 1.0988 1.0107 0.133 Uiso calc U . R 1 . .
H H38 0.088(2) 0.388(3) 0.6316(19) 0.077(12) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O8 C7 . 1.300(3) ?
O8 H8 . 0.82 ?
O59 C57 . 1.303(3) ?
O59 H59 . 0.82 ?
O38 C37 . 1.310(3) ?
O38 H38 . 0.817(10) ?
O28 C27 . 1.226(3) ?
O88 C87 . 1.307(3) ?
O88 H88 . 0.82 ?
O58 C57 . 1.215(3) ?
O78 C77 . 1.227(3) ?
O9 C7 . 1.219(3) ?
O39 C37 . 1.208(3) ?
O89 C87 . 1.209(3) ?
O90 C82 . 1.371(3) ?
O90 C91 . 1.421(4) ?
O40 C34 . 1.367(3) ?
O40 C41 . 1.427(4) ?
N73 C74 . 1.302(4) ?
N73 C72 . 1.307(4) ?
O10 C2 . 1.375(4) ?
O10 C11 . 1.425(4) ?
N23 C22 . 1.309(4) ?
N23 C24 . 1.310(4) ?
O60 C54 . 1.372(4) ?
O60 C61 . 1.425(4) ?
N79 C77 . 1.298(4) ?
N79 H79A . 0.86 ?
N79 H79B . 0.86 ?
N29 C27 . 1.300(4) ?
N29 H29A . 0.86 ?
N29 H29B . 0.86 ?
C36 C35 . 1.380(4) ?
C36 C31 . 1.382(4) ?
C36 C37 . 1.494(4) ?
C56 C55 . 1.385(4) ?
C56 C51 . 1.389(4) ?
C56 C57 . 1.491(4) ?
C76 C75 . 1.364(4) ?
C76 C71 . 1.365(4) ?
C76 C77 . 1.542(4) ?
C6 C1 . 1.384(4) ?
C6 C5 . 1.387(4) ?
C6 C7 . 1.496(4) ?
C26 C21 . 1.367(4) ?
C26 C25 . 1.370(4) ?
C26 C27 . 1.541(4) ?
C86 C81 . 1.378(4) ?
C86 C85 . 1.388(4) ?
C86 C87 . 1.488(4) ?
C81 C82 . 1.382(4) ?
C81 H81 . 0.93 ?
C35 C34 . 1.390(4) ?
C35 H35 . 0.93 ?
C34 C33 . 1.374(4) ?
C82 C83 . 1.383(4) ?
C1 C2 . 1.390(4) ?
C1 H1 . 0.93 ?
C55 C54 . 1.386(4) ?
C55 H55 . 0.93 ?
C24 C25 . 1.430(4) ?
C24 H24 . 0.93 ?
C22 C21 . 1.424(4) ?
C22 H22 . 0.93 ?
C21 H21 . 0.93 ?
C33 C32 . 1.387(4) ?
C33 H33 . 0.93 ?
C31 C32 . 1.387(4) ?
C31 H31 . 0.93 ?
C74 C75 . 1.431(4) ?
C74 H74 . 0.93 ?
C72 C71 . 1.436(4) ?
C72 H72 . 0.93 ?
C2 C3 . 1.386(4) ?
C25 H25 . 0.93 ?
C83 C84 . 1.392(4) ?
C83 H83 . 0.93 ?
C85 C84 . 1.372(4) ?
C85 H85 . 0.93 ?
C5 C4 . 1.379(4) ?
C5 H5 . 0.93 ?
C71 H71 . 0.93 ?
C75 H75 . 0.93 ?
C54 C53 . 1.388(5) ?
C51 C52 . 1.367(4) ?
C51 H51 . 0.93 ?
C32 H32 . 0.93 ?
C53 C52 . 1.381(5) ?
C53 H53 . 0.93 ?
C84 H84 . 0.93 ?
C3 C4 . 1.371(5) ?
C3 H3 . 0.93 ?
C4 H4 . 0.93 ?
C52 H52 . 0.93 ?
C91 H91A . 0.96 ?
C91 H91B . 0.96 ?
C91 H91C . 0.96 ?
C41 H41A . 0.96 ?
C41 H41B . 0.96 ?
C41 H41C . 0.96 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C61 H61A . 0.96 ?
C61 H61B . 0.96 ?
C61 H61C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O8 H8 . . 109.5 ?
C57 O59 H59 . . 109.5 ?
C37 O38 H38 . . 107.(3) ?
C87 O88 H88 . . 109.5 ?
C82 O90 C91 . . 117.7(3) ?
C34 O40 C41 . . 117.8(3) ?
C74 N73 C72 . . 121.8(3) ?
C2 O10 C11 . . 117.7(3) ?
C22 N23 C24 . . 121.4(3) ?
C54 O60 C61 . . 117.8(3) ?
C77 N79 H79A . . 120.0 ?
C77 N79 H79B . . 120.0 ?
H79A N79 H79B . . 120.0 ?
C27 N29 H29A . . 120.0 ?
C27 N29 H29B . . 120.0 ?
H29A N29 H29B . . 120.0 ?
C35 C36 C31 . . 120.1(3) ?
C35 C36 C37 . . 116.3(2) ?
C31 C36 C37 . . 123.7(3) ?
C55 C56 C51 . . 119.5(3) ?
C55 C56 C57 . . 121.5(3) ?
C51 C56 C57 . . 119.0(3) ?
C75 C76 C71 . . 120.7(3) ?
C75 C76 C77 . . 117.3(2) ?
C71 C76 C77 . . 122.0(2) ?
C1 C6 C5 . . 119.5(3) ?
C1 C6 C7 . . 121.1(2) ?
C5 C6 C7 . . 119.4(3) ?
C21 C26 C25 . . 119.9(3) ?
C21 C26 C27 . . 117.4(2) ?
C25 C26 C27 . . 122.7(2) ?
C81 C86 C85 . . 120.1(3) ?
C81 C86 C87 . . 116.7(2) ?
C85 C86 C87 . . 123.2(3) ?
O58 C57 O59 . . 122.5(3) ?
O58 C57 C56 . . 124.0(3) ?
O59 C57 C56 . . 113.5(3) ?
C86 C81 C82 . . 120.4(3) ?
C86 C81 H81 . . 119.8 ?
C82 C81 H81 . . 119.8 ?
O89 C87 O88 . . 123.2(3) ?
O89 C87 C86 . . 121.9(3) ?
O88 C87 C86 . . 114.9(3) ?
C36 C35 C34 . . 120.1(3) ?
C36 C35 H35 . . 119.9 ?
C34 C35 H35 . . 119.9 ?
O78 C77 N79 . . 125.0(3) ?
O78 C77 C76 . . 118.0(2) ?
N79 C77 C76 . . 117.0(2) ?
O40 C34 C33 . . 124.8(3) ?
O40 C34 C35 . . 115.0(3) ?
C33 C34 C35 . . 120.2(3) ?
O28 C27 N29 . . 124.6(3) ?
O28 C27 C26 . . 118.6(2) ?
N29 C27 C26 . . 116.7(2) ?
O90 C82 C81 . . 115.4(3) ?
O90 C82 C83 . . 124.7(3) ?
C81 C82 C83 . . 120.0(3) ?
O9 C7 O8 . . 122.9(3) ?
O9 C7 C6 . . 123.2(3) ?
O8 C7 C6 . . 113.9(3) ?
O39 C37 O38 . . 122.9(3) ?
O39 C37 C36 . . 122.3(3) ?
O38 C37 C36 . . 114.7(2) ?
C6 C1 C2 . . 120.4(3) ?
C6 C1 H1 . . 119.8 ?
C2 C1 H1 . . 119.8 ?
C56 C55 C54 . . 120.4(3) ?
C56 C55 H55 . . 119.8 ?
C54 C55 H55 . . 119.8 ?
N23 C24 C25 . . 120.7(3) ?
N23 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
N23 C22 C21 . . 121.4(3) ?
N23 C22 H22 . . 119.3 ?
C21 C22 H22 . . 119.3 ?
C26 C21 C22 . . 118.1(3) ?
C26 C21 H21 . . 120.9 ?
C22 C21 H21 . . 120.9 ?
C34 C33 C32 . . 119.6(3) ?
C34 C33 H33 . . 120.2 ?
C32 C33 H33 . . 120.2 ?
C36 C31 C32 . . 119.5(3) ?
C36 C31 H31 . . 120.2 ?
C32 C31 H31 . . 120.2 ?
N73 C74 C75 . . 121.5(3) ?
N73 C74 H74 . . 119.3 ?
C75 C74 H74 . . 119.3 ?
N73 C72 C71 . . 120.5(3) ?
N73 C72 H72 . . 119.8 ?
C71 C72 H72 . . 119.8 ?
O10 C2 C3 . . 124.8(3) ?
O10 C2 C1 . . 115.4(3) ?
C3 C2 C1 . . 119.9(3) ?
C26 C25 C24 . . 118.5(3) ?
C26 C25 H25 . . 120.8 ?
C24 C25 H25 . . 120.8 ?
C82 C83 C84 . . 119.3(3) ?
C82 C83 H83 . . 120.4 ?
C84 C83 H83 . . 120.4 ?
C84 C85 C86 . . 119.5(3) ?
C84 C85 H85 . . 120.2 ?
C86 C85 H85 . . 120.2 ?
C4 C5 C6 . . 119.5(3) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C76 C71 C72 . . 118.1(3) ?
C76 C71 H71 . . 121.0 ?
C72 C71 H71 . . 121.0 ?
C76 C75 C74 . . 117.5(3) ?
C76 C75 H75 . . 121.2 ?
C74 C75 H75 . . 121.2 ?
O60 C54 C55 . . 115.4(3) ?
O60 C54 C53 . . 124.8(3) ?
C55 C54 C53 . . 119.8(3) ?
C52 C51 C56 . . 119.7(3) ?
C52 C51 H51 . . 120.1 ?
C56 C51 H51 . . 120.1 ?
C33 C32 C31 . . 120.5(3) ?
C33 C32 H32 . . 119.7 ?
C31 C32 H32 . . 119.7 ?
C52 C53 C54 . . 119.1(3) ?
C52 C53 H53 . . 120.5 ?
C54 C53 H53 . . 120.5 ?
C85 C84 C83 . . 120.8(3) ?
C85 C84 H84 . . 119.6 ?
C83 C84 H84 . . 119.6 ?
C4 C3 C2 . . 119.2(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.5(3) ?
C3 C4 H4 . . 119.2 ?
C5 C4 H4 . . 119.2 ?
C51 C52 C53 . . 121.5(3) ?
C51 C52 H52 . . 119.2 ?
C53 C52 H52 . . 119.2 ?
O90 C91 H91A . . 109.5 ?
O90 C91 H91B . . 109.5 ?
H91A C91 H91B . . 109.5 ?
O90 C91 H91C . . 109.5 ?
H91A C91 H91C . . 109.5 ?
H91B C91 H91C . . 109.5 ?
O40 C41 H41A . . 109.5 ?
O40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
O40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
O10 C11 H11A . . 109.5 ?
O10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O60 C61 H61A . . 109.5 ?
O60 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
O60 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C55 C56 C57 O58 . . . . -176.7(3) ?
C51 C56 C57 O58 . . . . 4.3(4) ?
C55 C56 C57 O59 . . . . 2.1(4) ?
C51 C56 C57 O59 . . . . -176.8(3) ?
C85 C86 C81 C82 . . . . -0.5(4) ?
C87 C86 C81 C82 . . . . 178.9(3) ?
C81 C86 C87 O89 . . . . 0.4(4) ?
C85 C86 C87 O89 . . . . 179.7(3) ?
C81 C86 C87 O88 . . . . -179.8(3) ?
C85 C86 C87 O88 . . . . -0.4(4) ?
C31 C36 C35 C34 . . . . -1.2(4) ?
C37 C36 C35 C34 . . . . 178.6(3) ?
C75 C76 C77 O78 . . . . -2.7(4) ?
C71 C76 C77 O78 . . . . 177.0(3) ?
C75 C76 C77 N79 . . . . 177.7(3) ?
C71 C76 C77 N79 . . . . -2.5(4) ?
C41 O40 C34 C33 . . . . -5.8(5) ?
C41 O40 C34 C35 . . . . 175.2(3) ?
C36 C35 C34 O40 . . . . -179.7(3) ?
C36 C35 C34 C33 . . . . 1.2(5) ?
C21 C26 C27 O28 . . . . -1.8(4) ?
C25 C26 C27 O28 . . . . 177.7(3) ?
C21 C26 C27 N29 . . . . 178.8(3) ?
C25 C26 C27 N29 . . . . -1.6(4) ?
C91 O90 C82 C81 . . . . 172.3(3) ?
C91 O90 C82 C83 . . . . -8.3(5) ?
C86 C81 C82 O90 . . . . -179.8(3) ?
C86 C81 C82 C83 . . . . 0.7(5) ?
C1 C6 C7 O9 . . . . -176.1(3) ?
C5 C6 C7 O9 . . . . 4.2(4) ?
C1 C6 C7 O8 . . . . 3.6(4) ?
C5 C6 C7 O8 . . . . -176.1(3) ?
C35 C36 C37 O39 . . . . 0.8(4) ?
C31 C36 C37 O39 . . . . -179.4(3) ?
C35 C36 C37 O38 . . . . -179.4(3) ?
C31 C36 C37 O38 . . . . 0.3(4) ?
C5 C6 C1 C2 . . . . 0.2(4) ?
C7 C6 C1 C2 . . . . -179.4(3) ?
C51 C56 C55 C54 . . . . -0.2(4) ?
C57 C56 C55 C54 . . . . -179.1(3) ?
C22 N23 C24 C25 . . . . 0.1(4) ?
C24 N23 C22 C21 . . . . -0.1(4) ?
C25 C26 C21 C22 . . . . 0.2(4) ?
C27 C26 C21 C22 . . . . 179.8(2) ?
N23 C22 C21 C26 . . . . 0.0(4) ?
O40 C34 C33 C32 . . . . -179.5(3) ?
C35 C34 C33 C32 . . . . -0.6(5) ?
C35 C36 C31 C32 . . . . 0.5(5) ?
C37 C36 C31 C32 . . . . -179.2(3) ?
C72 N73 C74 C75 . . . . -0.7(4) ?
C74 N73 C72 C71 . . . . 0.8(4) ?
C11 O10 C2 C3 . . . . 3.8(5) ?
C11 O10 C2 C1 . . . . -176.6(3) ?
C6 C1 C2 O10 . . . . -179.6(3) ?
C6 C1 C2 C3 . . . . 0.1(5) ?
C21 C26 C25 C24 . . . . -0.3(4) ?
C27 C26 C25 C24 . . . . -179.9(2) ?
N23 C24 C25 C26 . . . . 0.2(4) ?
O90 C82 C83 C84 . . . . -179.7(3) ?
C81 C82 C83 C84 . . . . -0.3(5) ?
C81 C86 C85 C84 . . . . -0.1(5) ?
C87 C86 C85 C84 . . . . -179.4(3) ?
C1 C6 C5 C4 . . . . -0.3(5) ?
C7 C6 C5 C4 . . . . 179.4(3) ?
C75 C76 C71 C72 . . . . 0.3(4) ?
C77 C76 C71 C72 . . . . -179.4(2) ?
N73 C72 C71 C76 . . . . -0.6(4) ?
C71 C76 C75 C74 . . . . -0.2(4) ?
C77 C76 C75 C74 . . . . 179.5(2) ?
N73 C74 C75 C76 . . . . 0.4(4) ?
C61 O60 C54 C55 . . . . -178.3(3) ?
C61 O60 C54 C53 . . . . 1.3(5) ?
C56 C55 C54 O60 . . . . -179.8(3) ?
C56 C55 C54 C53 . . . . 0.7(5) ?
C55 C56 C51 C52 . . . . 0.4(5) ?
C57 C56 C51 C52 . . . . 179.3(3) ?
C34 C33 C32 C31 . . . . -0.1(5) ?
C36 C31 C32 C33 . . . . 0.1(5) ?
O60 C54 C53 C52 . . . . 179.1(3) ?
C55 C54 C53 C52 . . . . -1.4(5) ?
C86 C85 C84 C83 . . . . 0.5(5) ?
C82 C83 C84 C85 . . . . -0.3(5) ?
O10 C2 C3 C4 . . . . 179.3(3) ?
C1 C2 C3 C4 . . . . -0.4(5) ?
C2 C3 C4 C5 . . . . 0.3(5) ?
C6 C5 C4 C3 . . . . 0.0(5) ?
C56 C51 C52 C53 . . . . -1.2(5) ?
C54 C53 C52 C51 . . . . 1.6(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C61 H61B O40 2_677 0.96 2.58 3.491(5) 157.5 ?
C11 H11B O60 1_444 0.96 2.60 3.522(5) 160.5 ?
C41 H41B O90 1_566 0.96 2.47 3.401(5) 164.1 ?
C91 H91B O10 2_655 0.96 2.50 3.444(5) 168.8 ?
C71 H71 O9 . 0.93 2.48 3.393(4) 167.6 ?
C25 H25 O58 . 0.93 2.47 3.380(4) 167.7 ?
C72 H72 O58 1_455 0.93 2.65 3.262(4) 124.1 ?
C74 H74 O38 1_565 0.93 2.44 3.185(5) 137.1 ?
C22 H22 O88 . 0.93 2.43 3.183(4) 138.0 ?
C24 H24 O9 . 0.93 2.66 3.269(4) 124.0 ?
N29 H29B O58 . 0.86 2.07 2.889(4) 158.5 ?
N29 H29A O39 1_655 0.86 2.00 2.845(4) 166.1 ?
N79 H79B O9 . 0.86 2.06 2.875(4) 157.5 ?
N79 H79A O89 1_565 0.86 1.99 2.836(4) 166.1 ?
O88 H88 O78 1_545 0.82 1.86 2.678(3) 171.6 ?
O59 H59 N73 1_655 0.82 1.83 2.644(3) 173.6 ?
O8 H8 N23 . 0.82 1.83 2.642(3) 170.4 ?

####################################################################### 
# 
# 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_7H
_database_code_depnum_ccdc_archive 'CCDC 1538734'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            '7H Benzamide + 3-Fluorobenzoic Acid'
_chemical_formula_moiety         'C7 H5 F O2, C7 H7 N O'
_chemical_formula_sum            'C14 H12 F N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.25

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.222(4)
_cell_length_b                   8.817(7)
_cell_length_c                   14.578(11)
_cell_angle_alpha                101.606(18)
_cell_angle_beta                 94.434(16)
_cell_angle_gamma                94.826(18)
_cell_volume                     652.1(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    805
_cell_measurement_theta_min      2.5005
_cell_measurement_theta_max      18.6063
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'


_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            8127
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2397
_reflns_number_gt                1013
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1820
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.2046
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.973
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5532(8) -0.0036(5) 0.7373(3) 0.0709(13) Uani d . . . 1 . .
H H1 0.4027 -0.0635 0.7434 0.085 Uiso calc U . R 1 . .
C C2 0.6615(9) 0.1135(6) 0.8104(3) 0.0792(14) Uani d . . . 1 . .
C C3 0.8794(9) 0.2066(5) 0.8039(3) 0.0742(13) Uani d . . . 1 . .
H H3 0.9475 0.2869 0.8536 0.089 Uiso calc U . R 1 . .
C C4 0.9932(8) 0.1777(5) 0.7222(3) 0.0764(14) Uani d . . . 1 . .
H H4 1.1439 0.2382 0.7168 0.092 Uiso calc U . R 1 . .
C C5 0.8912(8) 0.0613(5) 0.6470(3) 0.0675(13) Uani d . . . 1 . .
H H5 0.9705 0.045 0.5913 0.081 Uiso calc U . R 1 . .
C C6 0.6692(7) -0.0312(5) 0.6551(2) 0.0530(10) Uani d . . . 1 . .
C C7 0.5513(7) -0.1618(5) 0.5769(3) 0.0563(11) Uani d . . . 1 . .
O O8 0.6826(6) -0.1789(4) 0.5018(2) 0.0787(10) Uani d . . D 1 . .
H H8 0.617(11) -0.256(5) 0.462(3) 0.16(3) Uiso d . . D 1 . .
O O9 0.3538(5) -0.2431(4) 0.58116(18) 0.0773(10) Uani d . . . 1 . .
F F10 0.5438(6) 0.1390(4) 0.89108(19) 0.1419(14) Uani d . . . 1 . .
C C11 0.0308(8) 0.3036(5) 0.2269(3) 0.0719(13) Uani d . . . 1 . .
H H11 -0.0778 0.2914 0.2731 0.086 Uiso calc U . R 1 . .
C C12 -0.0200(8) 0.2116(6) 0.1380(3) 0.0840(15) Uani d . . . 1 . .
H H12 -0.1629 0.1376 0.1249 0.101 Uiso calc U . R 1 . .
C C13 0.1370(9) 0.2275(6) 0.0684(3) 0.0818(15) Uani d . . . 1 . .
H H13 0.1012 0.1647 0.0085 0.098 Uiso calc U . R 1 . .
C C14 0.3477(9) 0.3373(6) 0.0883(3) 0.0888(16) Uani d . . . 1 . .
H H14 0.4535 0.3505 0.0414 0.107 Uiso calc U . R 1 . .
C C15 0.4029(8) 0.4286(5) 0.1783(3) 0.0745(14) Uani d . . . 1 . .
H H15 0.5492 0.5001 0.1917 0.089 Uiso calc U . R 1 . .
C C16 0.2445(7) 0.4150(4) 0.2480(2) 0.0502(10) Uani d . . . 1 . .
C C17 0.3117(7) 0.5170(4) 0.3427(2) 0.0548(11) Uani d . . . 1 . .
O O18 0.5363(5) 0.5848(3) 0.36458(18) 0.0705(9) Uani d . . . 1 . .
N N19 0.1330(7) 0.5339(5) 0.4030(2) 0.0732(12) Uani d . . D 1 . .
H H19A 0.178(7) 0.590(4) 0.4613(12) 0.077(14) Uiso d . . D 1 . .
H H19B -0.033(3) 0.503(5) 0.382(3) 0.104(17) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.372(5) ?
C1 C2 . 1.374(6) ?
C1 H1 . 0.93 ?
C2 F10 . 1.357(5) ?
C2 C3 . 1.366(6) ?
C3 C4 . 1.360(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.387(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.500(5) ?
C7 O9 . 1.219(4) ?
C7 O8 . 1.325(5) ?
O8 H8 . 0.826(10) ?
C11 C12 . 1.376(5) ?
C11 C16 . 1.395(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.375(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.375(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.389(6) ?
C14 H14 . 0.93 ?
C15 C16 . 1.376(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.487(5) ?
C17 O18 . 1.258(4) ?
C17 N19 . 1.327(5) ?
N19 H19A . 0.898(10) ?
N19 H19B . 0.894(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.3(4) ?
C6 C1 H1 . . 120.3 ?
C2 C1 H1 . . 120.3 ?
F10 C2 C3 . . 119.2(4) ?
F10 C2 C1 . . 118.4(4) ?
C3 C2 C1 . . 122.4(4) ?
C4 C3 C2 . . 117.7(4) ?
C4 C3 H3 . . 121.1 ?
C2 C3 H3 . . 121.1 ?
C3 C4 C5 . . 121.8(4) ?
C3 C4 H4 . . 119.1 ?
C5 C4 H4 . . 119.1 ?
C4 C5 C6 . . 119.4(4) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C1 C6 C5 . . 119.3(4) ?
C1 C6 C7 . . 118.6(3) ?
C5 C6 C7 . . 122.1(4) ?
O9 C7 O8 . . 123.3(4) ?
O9 C7 C6 . . 123.7(4) ?
O8 C7 C6 . . 113.0(3) ?
C7 O8 H8 . . 110.(4) ?
C12 C11 C16 . . 120.4(4) ?
C12 C11 H11 . . 119.8 ?
C16 C11 H11 . . 119.8 ?
C13 C12 C11 . . 121.0(4) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C14 . . 119.1(4) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C15 . . 120.1(4) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C16 C15 C14 . . 121.0(4) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C11 . . 118.3(4) ?
C15 C16 C17 . . 118.7(3) ?
C11 C16 C17 . . 123.0(3) ?
O18 C17 N19 . . 121.2(3) ?
O18 C17 C16 . . 119.6(3) ?
N19 C17 C16 . . 119.1(3) ?
C17 N19 H19A . . 119.(2) ?
C17 N19 H19B . . 120.(3) ?
H19A N19 H19B . . 121.(4) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 F10 . . . . -180.0(4) ?
C6 C1 C2 C3 . . . . 1.4(8) ?
F10 C2 C3 C4 . . . . 179.8(4) ?
C1 C2 C3 C4 . . . . -1.6(8) ?
C2 C3 C4 C5 . . . . 1.5(7) ?
C3 C4 C5 C6 . . . . -1.2(7) ?
C2 C1 C6 C5 . . . . -1.1(7) ?
C2 C1 C6 C7 . . . . 178.7(4) ?
C4 C5 C6 C1 . . . . 1.0(7) ?
C4 C5 C6 C7 . . . . -178.7(4) ?
C1 C6 C7 O9 . . . . 1.8(6) ?
C5 C6 C7 O9 . . . . -178.5(4) ?
C1 C6 C7 O8 . . . . -178.9(4) ?
C5 C6 C7 O8 . . . . 0.8(6) ?
C16 C11 C12 C13 . . . . -0.2(8) ?
C11 C12 C13 C14 . . . . 0.0(8) ?
C12 C13 C14 C15 . . . . 1.2(8) ?
C13 C14 C15 C16 . . . . -2.2(8) ?
C14 C15 C16 C11 . . . . 2.0(7) ?
C14 C15 C16 C17 . . . . -179.4(4) ?
C12 C11 C16 C15 . . . . -0.8(7) ?
C12 C11 C16 C17 . . . . -179.4(4) ?
C15 C16 C17 O18 . . . . -17.1(6) ?
C11 C16 C17 O18 . . . . 161.5(4) ?
C15 C16 C17 N19 . . . . 163.3(4) ?
C11 C16 C17 N19 . . . . -18.0(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O8 H8 O18 1_545 0.826(10) 1.785(17) 2.598(4) 168.(6) ?
N19 H19A O9 1_565 0.898(10) 2.132(14) 3.007(5) 165.(3) ?
N19 H19B O18 1_455 0.894(10) 2.43(3) 3.208(5) 145.(4) ?

####################################################################### 
# 
# 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_3G
_database_code_depnum_ccdc_archive 'CCDC 1538737'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        "4,4'-Bipyridyl 2-Fluorobenzoic Acid"
_chemical_name_common            "44'Bipyridyl + 2-Fluorobenzoic acid cocrystal"
_chemical_formula_moiety         'C10 H8 N2, C7 H5 F O2'
_chemical_formula_sum            'C17 H13 F N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         296.29

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.012(2)
_cell_length_b                   4.0528(8)
_cell_length_c                   32.335(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.648(4)
_cell_angle_gamma                90
_cell_volume                     1438.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3944
_cell_measurement_theta_min      2.5279
_cell_measurement_theta_max      23.3592
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed x-ray Tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21090
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40

_refine_special_details          
;
;

_reflns_number_total             2944
_reflns_number_gt                2002
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2075
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1157P)²+0.4639P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2011.12.3.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8707(3) -0.0425(7) 0.55909(8) 0.0638(7) Uani d . . . 1 . .
H H1 0.9526 -0.0014 0.5668 0.077 Uiso calc U . R 1 . .
C C2 0.8347(3) -0.1710(8) 0.52002(8) 0.0768(9) Uani d . . . 1 . .
H H2 0.8941 -0.2141 0.5019 0.092 Uiso calc U . R 1 . .
N N3 0.7189(2) -0.2346(6) 0.50752(7) 0.0713(7) Uani d . . . 1 . .
C C4 0.6355(3) -0.1735(8) 0.53338(8) 0.0698(8) Uani d . . . 1 . .
H H4 0.5546 -0.2199 0.5248 0.084 Uiso calc U . R 1 . .
C C5 0.6614(2) -0.0450(7) 0.57232(8) 0.0600(7) Uani d . . . 1 . .
H H5 0.599 -0.0031 0.5894 0.072 Uiso calc U . R 1 . .
C C6 0.7830(2) 0.0228(5) 0.58629(7) 0.0469(5) Uani d . . . 1 . .
C C7 0.81473(19) 0.1441(5) 0.62906(6) 0.0438(5) Uani d . . . 1 . .
C C8 0.7416(2) 0.0708(6) 0.66082(7) 0.0521(6) Uani d . . . 1 . .
H H8 0.6702 -0.0498 0.6553 0.063 Uiso calc U . R 1 . .
C C9 0.7751(2) 0.1775(7) 0.70072(7) 0.0577(6) Uani d . . . 1 . .
H H9 0.7249 0.1222 0.7215 0.069 Uiso calc U . R 1 . .
N N10 0.8740(2) 0.3532(6) 0.71126(6) 0.0603(6) Uani d . . . 1 . .
C C11 0.9437(2) 0.4258(7) 0.68055(8) 0.0582(6) Uani d . . . 1 . .
H H11 1.0138 0.5495 0.6871 0.07 Uiso calc U . R 1 . .
C C12 0.9188(2) 0.3296(6) 0.63982(7) 0.0502(6) Uani d . . . 1 . .
H H12 0.9709 0.388 0.6198 0.06 Uiso calc U . R 1 . .
C C21 0.7821(3) 0.1388(6) 0.34872(8) 0.0604(7) Uani d . . . 1 . .
H H21 0.8582 0.0934 0.3622 0.072 Uiso calc U . R 1 . .
C C22 0.7559(3) 0.0303(7) 0.30887(9) 0.0707(8) Uani d . . . 1 . .
H H22 0.8138 -0.0876 0.2956 0.085 Uiso calc U . R 1 . .
C C23 0.6430(3) 0.0964(7) 0.28837(8) 0.0703(8) Uani d . . . 1 . .
H H23 0.6252 0.0224 0.2613 0.084 Uiso calc U . R 1 . .
C C24 0.5579(3) 0.2695(7) 0.30777(8) 0.0659(8) Uani d . . . 1 . .
H H24 0.4821 0.3153 0.2942 0.079 Uiso calc U . R 1 . .
C C25 0.5863(2) 0.3757(6) 0.34802(8) 0.0560(6) Uani d . . . 1 . .
C C26 0.6977(2) 0.3149(6) 0.36943(7) 0.0485(6) Uani d . . . 1 . .
C C27 0.7370(2) 0.4332(7) 0.41272(8) 0.0592(7) Uani d . . . 1 . .
O O28 0.8424(2) 0.4390(7) 0.42563(6) 0.0918(8) Uani d . . . 1 . .
O O29 0.6481(2) 0.5281(7) 0.43354(7) 0.0858(7) Uani d . . . 1 . .
H H29 0.680(4) 0.589(12) 0.4582(16) 0.142(17) Uiso d . . . 1 . .
F F30 0.50193(15) 0.5458(5) 0.36602(6) 0.0915(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.384(3) ?
C1 C2 . 1.394(4) ?
C1 H1 . 0.93 ?
C2 N3 . 1.331(4) ?
C2 H2 . 0.93 ?
N3 C4 . 1.315(4) ?
C4 C5 . 1.371(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.405(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.483(3) ?
C7 C8 . 1.388(3) ?
C7 C12 . 1.391(3) ?
C8 C9 . 1.382(3) ?
C8 H8 . 0.93 ?
C9 N10 . 1.323(3) ?
C9 H9 . 0.93 ?
N10 C11 . 1.336(3) ?
C11 C12 . 1.380(3) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C21 C22 . 1.370(4) ?
C21 C26 . 1.387(3) ?
C21 H21 . 0.93 ?
C22 C23 . 1.387(4) ?
C22 H22 . 0.93 ?
C23 C24 . 1.363(4) ?
C23 H23 . 0.93 ?
C24 C25 . 1.382(4) ?
C24 H24 . 0.93 ?
C25 F30 . 1.328(3) ?
C25 C26 . 1.381(3) ?
C26 C27 . 1.509(3) ?
C27 O28 . 1.201(3) ?
C27 O29 . 1.291(3) ?
O29 H29 . 0.88(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.0(3) ?
C6 C1 H1 . . 120.5 ?
C2 C1 H1 . . 120.5 ?
N3 C2 C1 . . 122.9(3) ?
N3 C2 H2 . . 118.6 ?
C1 C2 H2 . . 118.6 ?
C4 N3 C2 . . 118.2(2) ?
N3 C4 C5 . . 123.4(3) ?
N3 C4 H4 . . 118.3 ?
C5 C4 H4 . . 118.3 ?
C4 C5 C6 . . 119.4(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C1 C6 C5 . . 117.0(2) ?
C1 C6 C7 . . 122.2(2) ?
C5 C6 C7 . . 120.7(2) ?
C8 C7 C12 . . 116.5(2) ?
C8 C7 C6 . . 120.8(2) ?
C12 C7 C6 . . 122.7(2) ?
C9 C8 C7 . . 119.8(2) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
N10 C9 C8 . . 124.1(2) ?
N10 C9 H9 . . 117.9 ?
C8 C9 H9 . . 117.9 ?
C9 N10 C11 . . 116.0(2) ?
N10 C11 C12 . . 124.4(2) ?
N10 C11 H11 . . 117.8 ?
C12 C11 H11 . . 117.8 ?
C11 C12 C7 . . 119.2(2) ?
C11 C12 H12 . . 120.4 ?
C7 C12 H12 . . 120.4 ?
C22 C21 C26 . . 121.4(3) ?
C22 C21 H21 . . 119.3 ?
C26 C21 H21 . . 119.3 ?
C21 C22 C23 . . 120.0(3) ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C24 C23 C22 . . 120.1(2) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 118.8(3) ?
C23 C24 H24 . . 120.6 ?
C25 C24 H24 . . 120.6 ?
F30 C25 C26 . . 119.8(2) ?
F30 C25 C24 . . 117.5(2) ?
C26 C25 C24 . . 122.7(2) ?
C25 C26 C21 . . 116.9(2) ?
C25 C26 C27 . . 125.8(2) ?
C21 C26 C27 . . 117.3(2) ?
O28 C27 O29 . . 124.4(3) ?
O28 C27 C26 . . 121.6(2) ?
O29 C27 C26 . . 113.9(2) ?
C27 O29 H29 . . 107.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 N3 . . . . -0.1(5) ?
C1 C2 N3 C4 . . . . -0.1(5) ?
C2 N3 C4 C5 . . . . 0.6(5) ?
N3 C4 C5 C6 . . . . -0.9(5) ?
C2 C1 C6 C5 . . . . -0.2(4) ?
C2 C1 C6 C7 . . . . 177.0(3) ?
C4 C5 C6 C1 . . . . 0.7(4) ?
C4 C5 C6 C7 . . . . -176.6(2) ?
C1 C6 C7 C8 . . . . -150.6(2) ?
C5 C6 C7 C8 . . . . 26.4(3) ?
C1 C6 C7 C12 . . . . 28.1(3) ?
C5 C6 C7 C12 . . . . -154.8(2) ?
C12 C7 C8 C9 . . . . -0.9(3) ?
C6 C7 C8 C9 . . . . 177.9(2) ?
C7 C8 C9 N10 . . . . 0.9(4) ?
C8 C9 N10 C11 . . . . -0.3(4) ?
C9 N10 C11 C12 . . . . -0.1(4) ?
N10 C11 C12 C7 . . . . -0.1(4) ?
C8 C7 C12 C11 . . . . 0.6(3) ?
C6 C7 C12 C11 . . . . -178.3(2) ?
C26 C21 C22 C23 . . . . 0.1(4) ?
C21 C22 C23 C24 . . . . 0.1(4) ?
C22 C23 C24 C25 . . . . -0.3(4) ?
C23 C24 C25 F30 . . . . 179.5(2) ?
C23 C24 C25 C26 . . . . 0.3(4) ?
F30 C25 C26 C21 . . . . -179.3(2) ?
C24 C25 C26 C21 . . . . -0.1(4) ?
F30 C25 C26 C27 . . . . -1.6(4) ?
C24 C25 C26 C27 . . . . 177.6(2) ?
C22 C21 C26 C25 . . . . 0.0(4) ?
C22 C21 C26 C27 . . . . -178.0(2) ?
C25 C26 C27 O28 . . . . -162.3(3) ?
C21 C26 C27 O28 . . . . 15.5(4) ?
C25 C26 C27 O29 . . . . 17.0(4) ?
C21 C26 C27 O29 . . . . -165.3(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O29 H29 N3 1_565 0.88(5) 1.77(5) 2.637(3) 169.(4) ?

####################################################################### 
# 
# 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_6B
_database_code_depnum_ccdc_archive 'CCDC 1538732'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Urea and 2-Nitrobenzoic Acid'
_chemical_formula_moiety         'C7 H5 N O4, C H4 N2 O'
_chemical_formula_sum            'C8 H9 N3 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         227.18

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.084(4)
_cell_length_b                   12.756(6)
_cell_length_c                   9.490(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.543(12)
_cell_angle_gamma                90
_cell_volume                     976.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      2.6784
_cell_measurement_theta_max      23.5903
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Brick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.105
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7065
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         26.69
_diffrn_reflns_theta_full        26.69
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             1904
_reflns_number_gt                1139
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2452
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.996
_refine_ls_number_reflns         1904
_refine_ls_number_parameters     157
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1633P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1197(4) 0.2606(2) 0.3695(3) 0.0370(7) Uani d . . . 1 . .
H H2A 0.111(5) 0.315(3) 0.1848(18) 0.065(11) Uiso d . . D 1 . .
H H2B 0.102(5) 0.3964(13) 0.303(4) 0.058(10) Uiso d . . D 1 . .
N N2 0.0939(4) 0.3331(2) 0.2698(3) 0.0526(8) Uani d . . D 1 . .
N N3 0.1026(4) 0.16072(18) 0.3317(3) 0.0527(8) Uani d . . . 1 . .
H H3A 0.1176 0.112 0.3938 0.063 Uiso calc U . R 1 . .
H H3B 0.0764 0.1448 0.2451 0.063 Uiso calc U . R 1 . .
O O4 0.1578(3) 0.28421(15) 0.4955(2) 0.0466(7) Uani d . . . 1 . .
N N5 0.2689(4) 0.93060(18) 0.5294(3) 0.0496(8) Uani d . . . 1 . .
C C6 0.3280(4) 0.8288(2) 0.5838(3) 0.0404(8) Uani d . . . 1 . .
C C7 0.2609(4) 0.7391(2) 0.5189(3) 0.0400(8) Uani d . . . 1 . .
H H7 0.1831 0.7438 0.4428 0.048 Uiso calc U . R 1 . .
C C8 0.3140(4) 0.6427(2) 0.5714(3) 0.0391(7) Uani d . . . 1 . .
C C9 0.4309(4) 0.6380(2) 0.6841(4) 0.0475(8) Uani d . . . 1 . .
H H9 0.4662 0.5731 0.719 0.057 Uiso calc U . R 1 . .
C C10 0.4960(5) 0.7286(2) 0.7457(4) 0.0483(8) Uani d . . . 1 . .
H H10 0.5745 0.7242 0.8214 0.058 Uiso calc U . R 1 . .
C C11 0.4450(4) 0.8251(2) 0.6953(4) 0.0489(8) Uani d . . . 1 . .
H H11 0.4885 0.8864 0.7357 0.059 Uiso calc U . R 1 . .
C C12 0.2417(4) 0.5457(2) 0.5030(3) 0.0411(8) Uani d . . . 1 . .
O O13 0.1493(3) 0.54792(16) 0.3977(3) 0.0593(8) Uani d . . . 1 . .
H H14 0.237(5) 0.407(2) 0.530(4) 0.084(14) Uiso d . . D 1 . .
O O14 0.2887(3) 0.45956(16) 0.5706(3) 0.0553(7) Uani d . . D 1 . .
O O15 0.1625(4) 0.9333(2) 0.4353(3) 0.0799(10) Uani d . . . 1 . .
O O16 0.3285(4) 1.0098(2) 0.5831(3) 0.0856(10) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 . 1.253(4) ?
C1 N3 . 1.328(4) ?
C1 N2 . 1.331(4) ?
N2 H2A . 0.859(10) ?
N2 H2B . 0.867(10) ?
N3 H3A . 0.86 ?
N3 H3B . 0.86 ?
N5 O15 . 1.201(4) ?
N5 O16 . 1.217(4) ?
N5 C6 . 1.466(4) ?
C6 C11 . 1.376(5) ?
C6 C7 . 1.393(4) ?
C7 C8 . 1.385(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.384(5) ?
C8 C12 . 1.500(4) ?
C9 C10 . 1.384(5) ?
C9 H9 . 0.93 ?
C10 C11 . 1.375(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 O13 . 1.211(4) ?
C12 O14 . 1.316(4) ?
O14 H14 . 0.864(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 C1 N3 . . 120.2(3) ?
O4 C1 N2 . . 122.0(3) ?
N3 C1 N2 . . 117.7(3) ?
C1 N2 H2A . . 117.(3) ?
C1 N2 H2B . . 113.(3) ?
H2A N2 H2B . . 126.(4) ?
C1 N3 H3A . . 120.0 ?
C1 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
O15 N5 O16 . . 122.3(3) ?
O15 N5 C6 . . 119.3(3) ?
O16 N5 C6 . . 118.4(3) ?
C11 C6 C7 . . 122.8(3) ?
C11 C6 N5 . . 119.6(3) ?
C7 C6 N5 . . 117.6(3) ?
C8 C7 C6 . . 117.8(3) ?
C8 C7 H7 . . 121.1 ?
C6 C7 H7 . . 121.1 ?
C9 C8 C7 . . 119.9(3) ?
C9 C8 C12 . . 121.9(3) ?
C7 C8 C12 . . 118.2(3) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 120.2(4) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C6 . . 118.4(3) ?
C10 C11 H11 . . 120.8 ?
C6 C11 H11 . . 120.8 ?
O13 C12 O14 . . 124.5(3) ?
O13 C12 C8 . . 122.8(3) ?
O14 C12 C8 . . 112.7(3) ?
C12 O14 H14 . . 108.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O15 N5 C6 C11 . . . . -177.4(3) ?
O16 N5 C6 C11 . . . . 1.7(5) ?
O15 N5 C6 C7 . . . . 2.4(5) ?
O16 N5 C6 C7 . . . . -178.6(3) ?
C11 C6 C7 C8 . . . . 0.9(5) ?
N5 C6 C7 C8 . . . . -178.8(2) ?
C6 C7 C8 C9 . . . . -0.5(4) ?
C6 C7 C8 C12 . . . . 179.5(2) ?
C7 C8 C9 C10 . . . . 0.0(5) ?
C12 C8 C9 C10 . . . . -180.0(3) ?
C8 C9 C10 C11 . . . . 0.0(5) ?
C9 C10 C11 C6 . . . . 0.4(5) ?
C7 C6 C11 C10 . . . . -0.8(5) ?
N5 C6 C11 C10 . . . . 178.9(3) ?
C9 C8 C12 O13 . . . . -174.1(3) ?
C7 C8 C12 O13 . . . . 5.9(4) ?
C9 C8 C12 O14 . . . . 6.5(4) ?
C7 C8 C12 O14 . . . . -173.5(3) ?

####################################################################### 
# 
# 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_1Q
_database_code_depnum_ccdc_archive 'CCDC 1538736'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Nicotinamide +  mToluic Acid from EtOH'
_chemical_formula_moiety         '2(C8 H8 O2), C6 H6 N2 O'
_chemical_formula_sum            'C22 H22 N2 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         394.41

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.878(3)
_cell_length_b                   12.704(4)
_cell_length_c                   15.328(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.034(9)
_cell_angle_gamma                90
_cell_volume                     2025.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2504
_cell_measurement_theta_min      2.5967
_cell_measurement_theta_max      21.8515
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Plate/Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            37173
_diffrn_reflns_av_R_equivalents  0.1220
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3550
_reflns_number_gt                1651
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.2008
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.5139P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6845(3) 0.3627(3) 0.8125(2) 0.0498(9) Uani d . . . 1 . .
H H1 0.6843 0.2902 0.8038 0.06 Uiso calc U . R 1 . .
N N2 0.7117(3) 0.3979(2) 0.8976(2) 0.0570(9) Uani d . . . 1 . .
C C3 0.7122(4) 0.5028(3) 0.9090(3) 0.0611(11) Uani d . . . 1 . .
H H3 0.7301 0.5293 0.968 0.073 Uiso calc U . R 1 . .
C C4 0.6874(4) 0.5726(3) 0.8376(3) 0.0652(12) Uani d . . . 1 . .
H H4 0.6905 0.6447 0.8486 0.078 Uiso calc U . R 1 . .
C C5 0.6578(3) 0.5348(3) 0.7492(3) 0.0593(11) Uani d . . . 1 . .
H H5 0.6394 0.581 0.7 0.071 Uiso calc U . R 1 . .
C C6 0.6562(3) 0.4263(3) 0.7353(2) 0.0446(9) Uani d . . . 1 . .
C C7 0.6245(3) 0.3766(3) 0.6442(2) 0.0470(9) Uani d . . . 1 . .
N N8 0.6182(3) 0.4349(2) 0.5718(2) 0.0640(9) Uani d . . . 1 . .
H H8A 0.5995 0.4063 0.5186 0.077 Uiso calc U . R 1 . .
H H8B 0.6327 0.5014 0.5777 0.077 Uiso calc U . R 1 . .
O O9 0.6039(3) 0.27972(19) 0.63779(16) 0.0649(8) Uani d . . . 1 . .
C C21 0.7942(4) 0.0193(3) 0.1333(3) 0.0631(11) Uani d . . . 1 . .
H H21 0.7758 -0.0178 0.0787 0.076 Uiso calc U . R 1 . .
C C22 0.8146(4) -0.0340(3) 0.2145(3) 0.0733(13) Uani d . . . 1 . .
H H22 0.8103 -0.1072 0.2145 0.088 Uiso calc U . R 1 . .
C C23 0.8413(4) 0.0200(3) 0.2955(3) 0.0704(13) Uani d . . . 1 . .
H H23 0.8534 -0.0171 0.3496 0.084 Uiso calc U . R 1 . .
C C24 0.8506(4) 0.1288(3) 0.2981(3) 0.0595(11) Uani d . . . 1 . .
C C25 0.8284(4) 0.1815(3) 0.2152(3) 0.0569(10) Uani d . . . 1 . .
H H25 0.8319 0.2546 0.2151 0.068 Uiso calc U . R 1 . .
C C26 0.8011(3) 0.1280(3) 0.1330(2) 0.0517(10) Uani d . . . 1 . .
C C27 0.7784(4) 0.1844(3) 0.0450(3) 0.0597(11) Uani d . . . 1 . .
O O28 0.7620(3) 0.2874(2) 0.05091(17) 0.0744(9) Uani d . . . 1 . .
H H28 0.7558 0.315 0.0014 0.112 Uiso calc U . R 1 . .
O O29 0.7723(3) 0.1419(2) -0.02730(19) 0.0814(9) Uani d . . . 1 . .
C C30 0.8823(5) 0.1884(4) 0.3869(3) 0.0851(15) Uani d . . . 1 . .
H H30A 0.9424 0.2435 0.3863 0.128 Uiso calc U . R 1 . .
H H30B 0.9195 0.1412 0.4365 0.128 Uiso calc U . R 1 . .
H H30C 0.8052 0.2185 0.3946 0.128 Uiso calc U . R 1 . .
C C31 0.5090(4) 0.0224(3) 0.3500(3) 0.0540(10) Uani d . . . 1 . .
H H31 0.5196 -0.0054 0.4079 0.065 Uiso calc U . R 1 . .
C C32 0.4853(4) -0.0430(3) 0.2753(3) 0.0627(11) Uani d . . . 1 . .
H H32 0.4817 -0.1154 0.2832 0.075 Uiso calc U . R 1 . .
C C33 0.4669(4) -0.0026(3) 0.1889(3) 0.0643(11) Uani d . . . 1 . .
H H33 0.4491 -0.048 0.1392 0.077 Uiso calc U . R 1 . .
C C34 0.4746(4) 0.1048(3) 0.1753(2) 0.0553(10) Uani d . . . 1 . .
C C35 0.4998(3) 0.1698(3) 0.2506(2) 0.0532(10) Uani d . . . 1 . .
H H35 0.5055 0.242 0.2426 0.064 Uiso calc U . R 1 . .
C C36 0.5168(3) 0.1308(3) 0.3380(2) 0.0473(9) Uani d . . . 1 . .
C C37 0.5399(4) 0.2054(3) 0.4153(2) 0.0525(10) Uani d . . . 1 . .
O O38 0.5490(3) 0.3002(2) 0.40730(17) 0.0818(10) Uani d . . . 1 . .
O O39 0.5498(3) 0.16017(19) 0.49427(16) 0.0708(9) Uani d . . . 1 . .
H H39 0.5651 0.205 0.5346 0.106 Uiso calc U . R 1 . .
C C40 0.4551(4) 0.1491(3) 0.0806(3) 0.0777(13) Uani d . . . 1 . .
H H40A 0.3661 0.1668 0.0542 0.117 Uiso calc U . R 1 . .
H H40B 0.4799 0.0975 0.0433 0.117 Uiso calc U . R 1 . .
H H40C 0.5068 0.2111 0.0843 0.117 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.329(4) ?
C1 C6 . 1.390(4) ?
C1 H1 . 0.93 ?
N2 C3 . 1.343(4) ?
C3 C4 . 1.372(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.383(5) ?
C4 H4 . 0.93 ?
C5 C6 . 1.394(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.479(5) ?
C7 O9 . 1.250(4) ?
C7 N8 . 1.319(4) ?
N8 H8A . 0.86 ?
N8 H8B . 0.86 ?
C21 C22 . 1.377(5) ?
C21 C26 . 1.383(5) ?
C21 H21 . 0.93 ?
C22 C23 . 1.373(6) ?
C22 H22 . 0.93 ?
C23 C24 . 1.386(5) ?
C23 H23 . 0.93 ?
C24 C25 . 1.392(5) ?
C24 C30 . 1.507(5) ?
C25 C26 . 1.386(5) ?
C25 H25 . 0.93 ?
C26 C27 . 1.484(5) ?
C27 O29 . 1.216(4) ?
C27 O28 . 1.327(4) ?
O28 H28 . 0.82 ?
C30 H30A . 0.96 ?
C30 H30B . 0.96 ?
C30 H30C . 0.96 ?
C31 C32 . 1.377(5) ?
C31 C36 . 1.396(5) ?
C31 H31 . 0.93 ?
C32 C33 . 1.379(5) ?
C32 H32 . 0.93 ?
C33 C34 . 1.387(5) ?
C33 H33 . 0.93 ?
C34 C35 . 1.380(5) ?
C34 C40 . 1.512(5) ?
C35 C36 . 1.388(5) ?
C35 H35 . 0.93 ?
C36 C37 . 1.480(5) ?
C37 O38 . 1.217(4) ?
C37 O39 . 1.315(4) ?
O39 H39 . 0.82 ?
C40 H40A . 0.96 ?
C40 H40B . 0.96 ?
C40 H40C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C6 . . 124.7(3) ?
N2 C1 H1 . . 117.6 ?
C6 C1 H1 . . 117.6 ?
C1 N2 C3 . . 116.9(3) ?
N2 C3 C4 . . 123.0(4) ?
N2 C3 H3 . . 118.5 ?
C4 C3 H3 . . 118.5 ?
C3 C4 C5 . . 119.5(4) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
C4 C5 C6 . . 118.8(4) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C1 C6 C5 . . 117.1(3) ?
C1 C6 C7 . . 119.2(3) ?
C5 C6 C7 . . 123.8(3) ?
O9 C7 N8 . . 121.5(3) ?
O9 C7 C6 . . 118.8(3) ?
N8 C7 C6 . . 119.7(3) ?
C7 N8 H8A . . 120.0 ?
C7 N8 H8B . . 120.0 ?
H8A N8 H8B . . 120.0 ?
C22 C21 C26 . . 120.0(4) ?
C22 C21 H21 . . 120.0 ?
C26 C21 H21 . . 120.0 ?
C23 C22 C21 . . 120.4(4) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 121.3(4) ?
C22 C23 H23 . . 119.4 ?
C24 C23 H23 . . 119.4 ?
C23 C24 C25 . . 117.5(4) ?
C23 C24 C30 . . 121.5(4) ?
C25 C24 C30 . . 121.1(4) ?
C26 C25 C24 . . 121.9(4) ?
C26 C25 H25 . . 119.1 ?
C24 C25 H25 . . 119.1 ?
C21 C26 C25 . . 118.9(4) ?
C21 C26 C27 . . 119.4(4) ?
C25 C26 C27 . . 121.7(3) ?
O29 C27 O28 . . 121.8(4) ?
O29 C27 C26 . . 124.3(4) ?
O28 C27 C26 . . 113.8(3) ?
C27 O28 H28 . . 109.5 ?
C24 C30 H30A . . 109.5 ?
C24 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C24 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C32 C31 C36 . . 119.3(3) ?
C32 C31 H31 . . 120.3 ?
C36 C31 H31 . . 120.3 ?
C31 C32 C33 . . 120.9(4) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C32 C33 C34 . . 120.8(4) ?
C32 C33 H33 . . 119.6 ?
C34 C33 H33 . . 119.6 ?
C35 C34 C33 . . 118.0(4) ?
C35 C34 C40 . . 121.2(4) ?
C33 C34 C40 . . 120.8(4) ?
C34 C35 C36 . . 122.1(3) ?
C34 C35 H35 . . 119.0 ?
C36 C35 H35 . . 119.0 ?
C35 C36 C31 . . 118.9(3) ?
C35 C36 C37 . . 119.2(3) ?
C31 C36 C37 . . 121.9(3) ?
O38 C37 O39 . . 122.6(3) ?
O38 C37 C36 . . 123.5(3) ?
O39 C37 C36 . . 113.9(3) ?
C37 O39 H39 . . 109.5 ?
C34 C40 H40A . . 109.5 ?
C34 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C34 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 N2 C3 . . . . -0.3(6) ?
C1 N2 C3 C4 . . . . -0.7(6) ?
N2 C3 C4 C5 . . . . 1.4(6) ?
C3 C4 C5 C6 . . . . -1.1(6) ?
N2 C1 C6 C5 . . . . 0.5(6) ?
N2 C1 C6 C7 . . . . -178.5(3) ?
C4 C5 C6 C1 . . . . 0.2(5) ?
C4 C5 C6 C7 . . . . 179.2(3) ?
C1 C6 C7 O9 . . . . 11.2(5) ?
C5 C6 C7 O9 . . . . -167.7(3) ?
C1 C6 C7 N8 . . . . -169.0(3) ?
C5 C6 C7 N8 . . . . 12.0(5) ?
C26 C21 C22 C23 . . . . 0.3(6) ?
C21 C22 C23 C24 . . . . -1.1(7) ?
C22 C23 C24 C25 . . . . 1.7(6) ?
C22 C23 C24 C30 . . . . -178.8(4) ?
C23 C24 C25 C26 . . . . -1.6(6) ?
C30 C24 C25 C26 . . . . 179.0(4) ?
C22 C21 C26 C25 . . . . -0.1(6) ?
C22 C21 C26 C27 . . . . -179.8(4) ?
C24 C25 C26 C21 . . . . 0.8(6) ?
C24 C25 C26 C27 . . . . -179.5(4) ?
C21 C26 C27 O29 . . . . -11.3(6) ?
C25 C26 C27 O29 . . . . 169.1(4) ?
C21 C26 C27 O28 . . . . 167.2(4) ?
C25 C26 C27 O28 . . . . -12.4(5) ?
C36 C31 C32 C33 . . . . -1.2(6) ?
C31 C32 C33 C34 . . . . 1.5(6) ?
C32 C33 C34 C35 . . . . -0.7(6) ?
C32 C33 C34 C40 . . . . 179.7(4) ?
C33 C34 C35 C36 . . . . -0.2(6) ?
C40 C34 C35 C36 . . . . 179.4(3) ?
C34 C35 C36 C31 . . . . 0.4(5) ?
C34 C35 C36 C37 . . . . -178.3(3) ?
C32 C31 C36 C35 . . . . 0.3(6) ?
C32 C31 C36 C37 . . . . 179.0(3) ?
C35 C36 C37 O38 . . . . -2.4(6) ?
C31 C36 C37 O38 . . . . 178.9(4) ?
C35 C36 C37 O39 . . . . 177.6(3) ?
C31 C36 C37 O39 . . . . -1.1(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N8 H8A O38 . 0.86 2.12 2.956(4) 164.9 ?
N8 H8B O29 2_655 0.86 2.31 3.046(4) 144.3 ?
O28 H28 N2 1_554 0.82 1.85 2.653(4) 165.6 ?
O39 H39 O9 . 0.82 1.79 2.595(3) 168.2 ?

####################################################################### 
# 
# 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_1A
_database_code_depnum_ccdc_archive 'CCDC 1538735'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Nicotinamide + 2Nitrobenzoic Acid from MeCN'
_chemical_formula_moiety         'C7 H5 N O4, C7 H4 N O4, C6 H7 N2 O'
_chemical_formula_sum            'C20 H16 N4 O9'
_chemical_formula_iupac          ?
_chemical_formula_weight         456.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.715(3)
_cell_length_b                   7.0371(7)
_cell_length_c                   21.947(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.132(4)
_cell_angle_gamma                90
_cell_volume                     4132.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7286
_cell_measurement_theta_min      2.7430
_cell_measurement_theta_max      25.9875
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888

_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22442
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3633
_reflns_number_gt                2875
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1092
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.157
_refine_ls_number_reflns         3633
_refine_ls_number_parameters     314
_refine_ls_number_restraints     20
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+3.0686P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.38483(7) 0.1466(3) 0.26047(8) 0.0441(4) Uani d . . . 1 . .
C C2 0.40375(8) 0.1384(3) 0.20806(9) 0.0590(6) Uani d . . . 1 . .
H H2 0.3994 0.0305 0.1827 0.071 Uiso calc U . R 1 . .
C C3 0.42926(9) 0.2940(4) 0.19431(10) 0.0675(7) Uani d . . . 1 . .
H H3 0.4425 0.2912 0.1595 0.081 Uiso calc U . R 1 . .
C C4 0.43520(8) 0.4527(4) 0.23164(11) 0.0637(6) Uani d . . . 1 . .
H H4 0.4521 0.5575 0.2217 0.076 Uiso calc U . R 1 . .
C C5 0.41627(7) 0.4587(3) 0.28411(9) 0.0504(5) Uani d . . . 1 . .
H H5 0.4207 0.5671 0.3092 0.061 Uiso calc U . R 1 . .
C C6 0.39074(6) 0.3047(3) 0.29946(8) 0.0394(4) Uani d . . . 1 . .
C C7 0.36688(7) 0.3219(3) 0.35301(9) 0.0427(4) Uani d . . . 1 . .
O O8 0.32173(6) 0.3072(3) 0.34378(7) 0.0740(5) Uani d . . . 1 . .
O O9 0.39825(6) 0.3600(2) 0.40622(6) 0.0553(4) Uani d . . D 1 . .
H H9 0.3873(10) 0.360(4) 0.4386(9) 0.098(10) Uiso d . . D 1 . .
N N10 0.35944(7) -0.0206(2) 0.27589(9) 0.0596(5) Uani d . . . 1 . .
O O11 0.36650(8) -0.0658(3) 0.33066(9) 0.0852(5) Uani d . . . 1 . .
O O12 0.33156(9) -0.1087(3) 0.23294(10) 0.1032(7) Uani d U . . 1 . .
C C21 0.30731(6) 0.6973(2) 0.58311(8) 0.0391(4) Uani d . . . 1 . .
H H21 0.3227 0.7166 0.5507 0.047 Uiso calc U . R 1 . .
N N22 0.31678(6) 0.5391(2) 0.61740(7) 0.0436(4) Uani d . . D 1 . .
H H22 0.3378(7) 0.452(3) 0.6107(11) 0.076(7) Uiso d . . D 1 . .
C C23 0.29562(8) 0.5055(3) 0.66405(10) 0.0535(5) Uani d . . . 1 . .
H H23 0.3032 0.3944 0.6876 0.064 Uiso calc U . R 1 . .
C C24 0.26274(9) 0.6331(3) 0.67774(11) 0.0629(6) Uani d . . . 1 . .
H H24 0.2476 0.6088 0.7101 0.075 Uiso calc U . R 1 . .
C C25 0.25224(8) 0.7983(3) 0.64296(9) 0.0519(5) Uani d . . . 1 . .
H H25 0.2299 0.8861 0.6518 0.062 Uiso calc U . R 1 . .
C C26 0.27491(6) 0.8335(2) 0.59494(8) 0.0358(4) Uani d . . . 1 . .
C C27 0.26665(6) 1.0081(2) 0.55433(8) 0.0366(4) Uani d . . . 1 . .
N N28 0.24124(6) 1.1498(2) 0.57097(9) 0.0487(4) Uani d . . . 1 . .
H H28A 0.2253(8) 1.137(3) 0.6001(11) 0.060(6) Uiso d . . . 1 . .
H H28B 0.2323(8) 1.250(3) 0.5454(10) 0.061(6) Uiso d . . . 1 . .
O O29 0.28371(5) 1.01457(18) 0.50780(6) 0.0510(4) Uani d . . . 1 . .
C C31 0.41655(7) 0.0928(2) 0.53773(8) 0.0385(4) Uani d . . . 1 . .
C C32 0.39604(8) -0.0334(3) 0.48965(10) 0.0517(5) Uani d . . . 1 . .
H H32 0.365 -0.0081 0.4622 0.062 Uiso calc U . R 1 . .
C C33 0.42176(10) -0.1985(3) 0.48224(12) 0.0663(6) Uani d U . . 1 . .
H H33 0.4077 -0.2829 0.4499 0.08 Uiso calc U . R 1 . .
C C34 0.46765(11) -0.2372(3) 0.52245(13) 0.0704(7) Uani d U . . 1 . .
H H34 0.4843 -0.3484 0.5172 0.084 Uiso calc U . R 1 . .
C C35 0.48934(9) -0.1138(3) 0.57030(11) 0.0622(6) Uani d . . . 1 . .
H H35 0.5205 -0.1395 0.5975 0.075 Uiso calc U . R 1 . .
C C36 0.46348(7) 0.0499(3) 0.57684(9) 0.0440(4) Uani d . . . 1 . .
N N37 0.48845(6) 0.1874(3) 0.62515(8) 0.0556(4) Uani d . . . 1 . .
O O38 0.48339(6) 0.3558(2) 0.61251(8) 0.0694(4) Uani d . . . 1 . .
O O39 0.51337(8) 0.1257(3) 0.67551(9) 0.1012(7) Uani d . . . 1 . .
C C40 0.38608(6) 0.2611(2) 0.54882(8) 0.0370(4) Uani d . . . 1 . .
O O41 0.37786(5) 0.27224(18) 0.60212(6) 0.0488(3) Uani d . . . 1 . .
O O42 0.36913(5) 0.37579(18) 0.50460(6) 0.0472(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.384(3) ?
C1 C6 . 1.387(2) ?
C1 N10 . 1.456(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.496(2) ?
C7 O8 . 1.219(2) ?
C7 O9 . 1.289(2) ?
O9 H9 . 0.843(10) ?
N10 O11 . 1.209(2) ?
N10 O12 . 1.221(2) ?
C21 N22 . 1.331(2) ?
C21 C26 . 1.383(2) ?
C21 H21 . 0.93 ?
N22 C23 . 1.327(3) ?
N22 H22 . 0.885(10) ?
C23 C24 . 1.367(3) ?
C23 H23 . 0.93 ?
C24 C25 . 1.380(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.383(3) ?
C25 H25 . 0.93 ?
C26 C27 . 1.500(2) ?
C27 O29 . 1.233(2) ?
C27 N28 . 1.326(2) ?
N28 H28A . 0.87(2) ?
N28 H28B . 0.90(2) ?
C31 C32 . 1.383(3) ?
C31 C36 . 1.392(3) ?
C31 C40 . 1.510(2) ?
C32 C33 . 1.394(3) ?
C32 H32 . 0.93 ?
C33 C34 . 1.373(4) ?
C33 H33 . 0.93 ?
C34 C35 . 1.374(4) ?
C34 H34 . 0.93 ?
C35 C36 . 1.384(3) ?
C35 H35 . 0.93 ?
C36 N37 . 1.468(3) ?
N37 O38 . 1.217(2) ?
N37 O39 . 1.220(2) ?
C40 O41 . 1.251(2) ?
C40 O42 . 1.255(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 122.45(19) ?
C2 C1 N10 . . 118.08(18) ?
C6 C1 N10 . . 119.43(16) ?
C3 C2 C1 . . 118.4(2) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C4 C3 C2 . . 120.33(19) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C3 C4 C5 . . 120.7(2) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.49(19) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 117.63(16) ?
C5 C6 C7 . . 119.15(16) ?
C1 C6 C7 . . 122.97(17) ?
O8 C7 O9 . . 126.08(18) ?
O8 C7 C6 . . 120.51(17) ?
O9 C7 C6 . . 113.36(16) ?
C7 O9 H9 . . 117.(2) ?
O11 N10 O12 . . 122.7(2) ?
O11 N10 C1 . . 118.79(18) ?
O12 N10 C1 . . 118.55(19) ?
N22 C21 C26 . . 121.02(16) ?
N22 C21 H21 . . 119.5 ?
C26 C21 H21 . . 119.5 ?
C23 N22 C21 . . 121.56(16) ?
C23 N22 H22 . . 116.5(16) ?
C21 N22 H22 . . 121.9(16) ?
N22 C23 C24 . . 120.42(18) ?
N22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
C23 C24 C25 . . 119.24(19) ?
C23 C24 H24 . . 120.4 ?
C25 C24 H24 . . 120.4 ?
C24 C25 C26 . . 120.01(17) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 117.74(16) ?
C25 C26 C27 . . 124.76(15) ?
C21 C26 C27 . . 117.50(15) ?
O29 C27 N28 . . 123.13(17) ?
O29 C27 C26 . . 119.35(15) ?
N28 C27 C26 . . 117.51(16) ?
C27 N28 H28A . . 122.0(14) ?
C27 N28 H28B . . 120.1(14) ?
H28A N28 H28B . . 115.(2) ?
C32 C31 C36 . . 117.58(17) ?
C32 C31 C40 . . 119.38(17) ?
C36 C31 C40 . . 122.87(16) ?
C31 C32 C33 . . 120.2(2) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C34 C33 C32 . . 120.4(2) ?
C34 C33 H33 . . 119.8 ?
C32 C33 H33 . . 119.8 ?
C33 C34 C35 . . 120.9(2) ?
C33 C34 H34 . . 119.6 ?
C35 C34 H34 . . 119.6 ?
C34 C35 C36 . . 118.0(2) ?
C34 C35 H35 . . 121.0 ?
C36 C35 H35 . . 121.0 ?
C35 C36 C31 . . 122.9(2) ?
C35 C36 N37 . . 117.66(19) ?
C31 C36 N37 . . 119.39(16) ?
O38 N37 O39 . . 123.9(2) ?
O38 N37 C36 . . 118.19(17) ?
O39 N37 C36 . . 117.9(2) ?
O41 C40 O42 . . 124.02(15) ?
O41 C40 C31 . . 116.47(15) ?
O42 C40 C31 . . 119.46(15) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.2(3) ?
N10 C1 C2 C3 . . . . -177.93(19) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C1 . . . . -0.3(3) ?
C4 C5 C6 C7 . . . . -174.65(18) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
N10 C1 C6 C5 . . . . 178.27(17) ?
C2 C1 C6 C7 . . . . 174.71(18) ?
N10 C1 C6 C7 . . . . -7.6(3) ?
C5 C6 C7 O8 . . . . 117.5(2) ?
C1 C6 C7 O8 . . . . -56.6(3) ?
C5 C6 C7 O9 . . . . -59.9(2) ?
C1 C6 C7 O9 . . . . 126.03(19) ?
C2 C1 N10 O11 . . . . 139.8(2) ?
C6 C1 N10 O11 . . . . -38.0(3) ?
C2 C1 N10 O12 . . . . -40.7(3) ?
C6 C1 N10 O12 . . . . 141.4(2) ?
C26 C21 N22 C23 . . . . 0.1(3) ?
C21 N22 C23 C24 . . . . 0.8(3) ?
N22 C23 C24 C25 . . . . -0.7(4) ?
C23 C24 C25 C26 . . . . -0.1(4) ?
C24 C25 C26 C21 . . . . 0.8(3) ?
C24 C25 C26 C27 . . . . -179.63(19) ?
N22 C21 C26 C25 . . . . -0.9(3) ?
N22 C21 C26 C27 . . . . 179.58(16) ?
C25 C26 C27 O29 . . . . -170.85(19) ?
C21 C26 C27 O29 . . . . 8.7(2) ?
C25 C26 C27 N28 . . . . 9.5(3) ?
C21 C26 C27 N28 . . . . -170.92(17) ?
C36 C31 C32 C33 . . . . 1.1(3) ?
C40 C31 C32 C33 . . . . -174.23(17) ?
C31 C32 C33 C34 . . . . -0.1(3) ?
C32 C33 C34 C35 . . . . -0.6(3) ?
C33 C34 C35 C36 . . . . 0.2(3) ?
C34 C35 C36 C31 . . . . 0.8(3) ?
C34 C35 C36 N37 . . . . -175.73(18) ?
C32 C31 C36 C35 . . . . -1.5(3) ?
C40 C31 C36 C35 . . . . 173.67(17) ?
C32 C31 C36 N37 . . . . 174.99(16) ?
C40 C31 C36 N37 . . . . -9.8(2) ?
C35 C36 N37 O38 . . . . 140.21(19) ?
C31 C36 N37 O38 . . . . -36.5(2) ?
C35 C36 N37 O39 . . . . -39.3(3) ?
C31 C36 N37 O39 . . . . 144.0(2) ?
C32 C31 C40 O41 . . . . 120.54(19) ?
C36 C31 C40 O41 . . . . -54.6(2) ?
C32 C31 C40 O42 . . . . -56.9(2) ?
C36 C31 C40 O42 . . . . 128.00(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N22 H22 O41 . 0.885(10) 1.724(10) 2.6076(19) 176.(2) ?
O9 H9 O42 . 0.843(10) 1.656(10) 2.4970(18) 175.(3) ?
N28 H28B O29 7_576 0.90(2) 2.01(2) 2.902(2) 176.(2) ?
N28 H28A O8 7_566 0.87(2) 2.05(2) 2.889(2) 161.(2) ?
C23 H23 O12 6_556 0.93 2.29 3.207(3) 168.9 ?

####################################################################### 
# 
# 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_1J
_database_code_depnum_ccdc_archive 'CCDC 1538740'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Nicotinamide + 2Aminobenzoic Acid from EtOH'
_chemical_formula_moiety         'C7 H7 N O2, C6 H6 N2 O'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.26
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.479(2)
_cell_length_b                   4.9873(9)
_cell_length_c                   12.644(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.361(5)
_cell_angle_gamma                90
_cell_volume                     623.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3190
_cell_measurement_theta_min      3.0814
_cell_measurement_theta_max      25.6775
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Plate/Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9087
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
    'Refined as a 2-component inversion twin. 
The Flack parameter is meaningless due to 
Mo radiation for a light atom structure'
;


_reflns_number_total             2364
_reflns_number_gt                2141
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0744
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2364
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+0.0525P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.142
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 856 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0787(2) 0.8813(5) 0.68144(18) 0.0471(5) Uani d . . . 1 . .
C C2 -0.0134(2) 0.7129(5) 0.7082(2) 0.0606(7) Uani d . . . 1 . .
H H2 -0.0613 0.5864 0.6561 0.073 Uiso calc U . R 1 . .
C C3 -0.0342(3) 0.7301(5) 0.8083(3) 0.0661(8) Uani d . . . 1 . .
H H3 -0.0964 0.6162 0.8232 0.079 Uiso calc U . R 1 . .
C C4 0.0356(2) 0.9142(6) 0.8888(2) 0.0600(7) Uani d . . . 1 . .
H H4 0.021 0.9244 0.9574 0.072 Uiso calc U . R 1 . .
C C5 0.1265(2) 1.0808(5) 0.86529(19) 0.0473(5) Uani d . . . 1 . .
H H5 0.1735 1.2055 0.9187 0.057 Uiso calc U . R 1 . .
C C6 0.1505(2) 1.0682(5) 0.76314(18) 0.0395(5) Uani d . . . 1 . .
C C7 0.2494(2) 1.2516(4) 0.74230(16) 0.0415(5) Uani d . . . 1 . .
O O8 0.31317(16) 1.4066(4) 0.82782(13) 0.0529(4) Uani d . . . 1 . .
H H8A 0.371(3) 1.524(8) 0.808(3) 0.096(11) Uiso d . . . 1 . .
O O9 0.27321(19) 1.2637(4) 0.65458(14) 0.0652(5) Uani d . . . 1 . .
N N10 0.0924(3) 0.8617(6) 0.57744(18) 0.0672(7) Uani d . . . 1 . .
H H10A 0.060(3) 0.712(8) 0.541(3) 0.085(10) Uiso d . . . 1 . .
H H10B 0.170(3) 0.949(7) 0.573(2) 0.075(10) Uiso d . . . 1 . .
C C21 0.5287(2) 0.8068(5) 0.71258(17) 0.0434(5) Uani d . . . 1 . .
H H21 0.4879 0.7082 0.6477 0.052 Uiso calc U . R 1 . .
N N22 0.49379(18) 0.7545(4) 0.80244(15) 0.0482(5) Uani d . . . 1 . .
C C23 0.5543(2) 0.8917(6) 0.89530(18) 0.0506(6) Uani d . . . 1 . .
H H23 0.5318 0.8535 0.9589 0.061 Uiso calc U . R 1 . .
C C24 0.6486(3) 1.0874(6) 0.9020(2) 0.0558(6) Uani d . . . 1 . .
H H24 0.6894 1.1796 0.9687 0.067 Uiso calc U . R 1 . .
C C25 0.6814(2) 1.1439(5) 0.8079(2) 0.0488(6) Uani d . . . 1 . .
H H25 0.7434 1.2788 0.8097 0.059 Uiso calc U . R 1 . .
C C26 0.6224(2) 1.0002(4) 0.71067(17) 0.0362(5) Uani d . . . 1 . .
C C27 0.6607(2) 1.0578(5) 0.60906(18) 0.0409(5) Uani d . . . 1 . .
O O28 0.69416(19) 1.2858(3) 0.59138(15) 0.0609(5) Uani d . . . 1 . .
N N29 0.6551(2) 0.8528(4) 0.54095(16) 0.0485(5) Uani d . . . 1 . .
H H29A 0.680(2) 0.885(6) 0.4823(19) 0.049(6) Uiso d . . . 1 . .
H H29B 0.647(3) 0.686(7) 0.562(2) 0.061(8) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N10 . 1.373(3) ?
C1 C2 . 1.402(3) ?
C1 C6 . 1.410(3) ?
C2 C3 . 1.356(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.386(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.397(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.470(3) ?
C7 O9 . 1.216(2) ?
C7 O8 . 1.317(3) ?
O8 H8A . 0.94(4) ?
N10 H10A . 0.88(4) ?
N10 H10B . 0.94(3) ?
C21 N22 . 1.330(2) ?
C21 C26 . 1.383(3) ?
C21 H21 . 0.93 ?
N22 C23 . 1.325(3) ?
C23 C24 . 1.372(4) ?
C23 H23 . 0.93 ?
C24 C25 . 1.373(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.380(3) ?
C25 H25 . 0.93 ?
C26 C27 . 1.495(3) ?
C27 O28 . 1.232(3) ?
C27 N29 . 1.325(3) ?
N29 H29A . 0.88(2) ?
N29 H29B . 0.89(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N10 C1 C2 . . 119.1(2) ?
N10 C1 C6 . . 123.3(2) ?
C2 C1 C6 . . 117.5(2) ?
C3 C2 C1 . . 121.6(2) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C2 C3 C4 . . 121.2(2) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 118.5(2) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C4 C5 C6 . . 121.7(2) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 119.4(2) ?
C5 C6 C7 . . 119.5(2) ?
C1 C6 C7 . . 121.12(19) ?
O9 C7 O8 . . 121.2(2) ?
O9 C7 C6 . . 124.4(2) ?
O8 C7 C6 . . 114.45(17) ?
C7 O8 H8A . . 110.(2) ?
C1 N10 H10A . . 115.(2) ?
C1 N10 H10B . . 113.2(18) ?
H10A N10 H10B . . 123.(3) ?
N22 C21 C26 . . 123.36(19) ?
N22 C21 H21 . . 118.3 ?
C26 C21 H21 . . 118.3 ?
C23 N22 C21 . . 118.02(19) ?
N22 C23 C24 . . 123.1(2) ?
N22 C23 H23 . . 118.5 ?
C24 C23 H23 . . 118.5 ?
C23 C24 C25 . . 118.3(2) ?
C23 C24 H24 . . 120.8 ?
C25 C24 H24 . . 120.8 ?
C24 C25 C26 . . 119.9(2) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 117.26(19) ?
C25 C26 C27 . . 119.81(19) ?
C21 C26 C27 . . 122.93(19) ?
O28 C27 N29 . . 123.2(2) ?
O28 C27 C26 . . 120.4(2) ?
N29 C27 C26 . . 116.3(2) ?
C27 N29 H29A . . 116.6(18) ?
C27 N29 H29B . . 121.0(18) ?
H29A N29 H29B . . 121.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N10 C1 C2 C3 . . . . -177.8(2) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
C1 C2 C3 C4 . . . . -0.5(4) ?
C2 C3 C4 C5 . . . . 0.2(4) ?
C3 C4 C5 C6 . . . . -0.3(4) ?
C4 C5 C6 C1 . . . . 0.6(4) ?
C4 C5 C6 C7 . . . . -179.9(2) ?
N10 C1 C6 C5 . . . . 177.6(2) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
N10 C1 C6 C7 . . . . -1.9(3) ?
C2 C1 C6 C7 . . . . 179.7(2) ?
C5 C6 C7 O9 . . . . -176.8(2) ?
C1 C6 C7 O9 . . . . 2.7(3) ?
C5 C6 C7 O8 . . . . 3.4(3) ?
C1 C6 C7 O8 . . . . -177.08(19) ?
C26 C21 N22 C23 . . . . -1.4(3) ?
C21 N22 C23 C24 . . . . 1.3(4) ?
N22 C23 C24 C25 . . . . 0.2(4) ?
C23 C24 C25 C26 . . . . -1.6(4) ?
C24 C25 C26 C21 . . . . 1.6(3) ?
C24 C25 C26 C27 . . . . -178.6(2) ?
N22 C21 C26 C25 . . . . 0.0(3) ?
N22 C21 C26 C27 . . . . -179.9(2) ?
C25 C26 C27 O28 . . . . -31.2(3) ?
C21 C26 C27 O28 . . . . 148.7(2) ?
C25 C26 C27 N29 . . . . 149.4(2) ?
C21 C26 C27 N29 . . . . -30.8(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O8 H8A N22 1_565 0.94(4) 1.74(4) 2.664(2) 167.(3) ?
N10 H10A N10 2_546 0.88(4) 2.50(4) 3.359(3) 164.(3) ?
N10 H10B O9 . 0.94(3) 1.99(3) 2.709(4) 132.(2) ?
N29 H29A O9 2_646 0.88(2) 2.04(2) 2.847(2) 152.(3) ?
N29 H29B O28 1_545 0.89(3) 2.06(3) 2.898(3) 157.(2) ?

####################################################################### 
# 
# 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_6A
_database_code_depnum_ccdc_archive 'CCDC 1538739'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Urea + 2Nitrobenzoic Acid from MecN'
_chemical_formula_moiety         '2(C7 H5 N O4), C H4 N2 O'
_chemical_formula_sum            'C15 H14 N4 O9'
_chemical_formula_iupac          ?
_chemical_formula_weight         394.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8242(18)
_cell_length_b                   10.0350(15)
_cell_length_c                   15.060(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.953(2)
_cell_angle_gamma                90
_cell_volume                     1726.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7970
_cell_measurement_theta_min      2.4655
_cell_measurement_theta_max      24.9711
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'


_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22669
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3077
_reflns_number_gt                2530
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1012
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     277
_refine_ls_number_restraints     6
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.3329P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.69431(14) 0.61853(16) 0.68141(11) 0.0484(4) Uani d . . . 1 . .
H H1 0.7365 0.5401 0.6976 0.058 Uiso calc U . R 1 . .
C C2 0.68124(15) 0.70385(17) 0.74946(11) 0.0545(4) Uani d . . . 1 . .
H H2 0.7162 0.6837 0.8107 0.065 Uiso calc U . R 1 . .
C C3 0.61704(15) 0.81830(17) 0.72756(11) 0.0537(4) Uani d . . . 1 . .
H H3 0.6061 0.8741 0.774 0.064 Uiso calc U . R 1 . .
C C4 0.56882(14) 0.85062(16) 0.63724(11) 0.0508(4) Uani d . . . 1 . .
H H4 0.5259 0.9287 0.6218 0.061 Uiso calc U . R 1 . .
C C5 0.58482(12) 0.76574(14) 0.56972(10) 0.0402(3) Uani d . . . 1 . .
C C6 0.64605(12) 0.64666(14) 0.58906(10) 0.0396(3) Uani d . . . 1 . .
C C7 0.65220(12) 0.54931(14) 0.51610(10) 0.0409(3) Uani d . . . 1 . .
O O8 0.73094(11) 0.45639(12) 0.54510(8) 0.0631(4) Uani d . . D 1 . .
H H8 0.7259(19) 0.3995(18) 0.5034(11) 0.088(7) Uiso d . . D 1 . .
O O9 0.58941(9) 0.55410(10) 0.43895(7) 0.0508(3) Uani d . . . 1 . .
N N10 0.53872(12) 0.81129(13) 0.47483(9) 0.0495(3) Uani d . . . 1 . .
O O11 0.60807(12) 0.84580(13) 0.43288(8) 0.0690(4) Uani d . . . 1 . .
O O12 0.43428(12) 0.81768(19) 0.44412(10) 0.0941(5) Uani d . . . 1 . .
C C13 0.69983(13) 0.26442(16) 0.33986(11) 0.0462(4) Uani d . . . 1 . .
O O14 0.73122(10) 0.26453(11) 0.42612(7) 0.0543(3) Uani d . . . 1 . .
N N15 0.65153(15) 0.37302(16) 0.29458(11) 0.0608(4) Uani d . . D 1 . .
H H15A 0.6298(16) 0.4379(16) 0.3266(12) 0.074(6) Uiso d . . D 1 . .
H H15B 0.6263(16) 0.371(2) 0.2350(7) 0.070(6) Uiso d . . D 1 . .
N N16 0.71443(15) 0.15682(16) 0.29326(10) 0.0620(4) Uani d . . D 1 . .
H H16A 0.6983(16) 0.157(2) 0.2328(7) 0.073(6) Uiso d . . D 1 . .
H H16B 0.7579(14) 0.0905(15) 0.3219(12) 0.070(6) Uiso d . . D 1 . .
C C21 0.92104(14) 0.89027(16) 0.66328(10) 0.0478(4) Uani d . . . 1 . .
H H21 0.8944 0.9707 0.6809 0.057 Uiso calc U . R 1 . .
C C22 0.97570(15) 0.80121(18) 0.72981(11) 0.0554(4) Uani d . . . 1 . .
H H22 0.9849 0.8214 0.7915 0.067 Uiso calc U . R 1 . .
C C23 1.01668(16) 0.68280(18) 0.70549(12) 0.0606(5) Uani d . . . 1 . .
H H23 1.0541 0.623 0.7507 0.073 Uiso calc U . R 1 . .
C C24 1.00265(16) 0.65223(17) 0.61456(12) 0.0571(4) Uani d . . . 1 . .
H H24 1.0307 0.5721 0.5976 0.069 Uiso calc U . R 1 . .
C C25 0.94637(13) 0.74183(14) 0.54872(10) 0.0416(3) Uani d . . . 1 . .
C C26 0.90459(12) 0.86322(14) 0.57053(10) 0.0386(3) Uani d . . . 1 . .
C C27 0.85202(12) 0.96386(14) 0.49909(10) 0.0415(3) Uani d . . . 1 . .
H H28 0.7776(18) 1.1189(17) 0.4913(11) 0.084(7) Uiso d . . D 1 . .
O O28 0.80127(12) 1.06039(12) 0.53164(8) 0.0637(4) Uani d . . D 1 . .
O O29 0.85824(10) 0.95630(11) 0.42042(7) 0.0535(3) Uani d . . . 1 . .
N N30 0.92872(13) 0.70063(13) 0.45314(9) 0.0517(4) Uani d . . . 1 . .
O O31 1.01019(14) 0.70031(19) 0.41985(11) 0.0992(6) Uani d . . . 1 . .
O O32 0.83264(13) 0.66269(16) 0.41283(9) 0.0820(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.374(2) ?
C1 C6 . 1.389(2) ?
C1 H1 . 0.93 ?
C2 C3 . 1.369(2) ?
C2 H2 . 0.93 ?
C3 C4 . 1.371(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.376(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.389(2) ?
C5 N10 . 1.4650(19) ?
C6 C7 . 1.486(2) ?
C7 O9 . 1.2075(17) ?
C7 O8 . 1.3105(18) ?
O8 H8 . 0.839(10) ?
N10 O12 . 1.2035(18) ?
N10 O11 . 1.2078(18) ?
C13 O14 . 1.2555(19) ?
C13 N16 . 1.323(2) ?
C13 N15 . 1.333(2) ?
N15 H15A . 0.887(9) ?
N15 H15B . 0.870(9) ?
N16 H16A . 0.880(9) ?
N16 H16B . 0.882(9) ?
C21 C22 . 1.373(2) ?
C21 C26 . 1.387(2) ?
C21 H21 . 0.93 ?
C22 C23 . 1.368(3) ?
C22 H22 . 0.93 ?
C23 C24 . 1.371(2) ?
C23 H23 . 0.93 ?
C24 C25 . 1.376(2) ?
C24 H24 . 0.93 ?
C25 C26 . 1.386(2) ?
C25 N30 . 1.460(2) ?
C26 C27 . 1.489(2) ?
C27 O29 . 1.2081(17) ?
C27 O28 . 1.3003(18) ?
O28 H28 . 0.839(10) ?
N30 O31 . 1.1952(19) ?
N30 O32 . 1.2035(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.58(15) ?
C2 C1 H1 . . 119.2 ?
C6 C1 H1 . . 119.2 ?
C3 C2 C1 . . 120.32(15) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 120.01(16) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.03(16) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C6 . . 122.76(14) ?
C4 C5 N10 . . 116.11(13) ?
C6 C5 N10 . . 121.05(13) ?
C5 C6 C1 . . 116.24(14) ?
C5 C6 C7 . . 122.20(13) ?
C1 C6 C7 . . 121.39(13) ?
O9 C7 O8 . . 123.82(14) ?
O9 C7 C6 . . 123.37(13) ?
O8 C7 C6 . . 112.79(12) ?
C7 O8 H8 . . 109.1(15) ?
O12 N10 O11 . . 123.48(15) ?
O12 N10 C5 . . 118.56(14) ?
O11 N10 C5 . . 117.89(13) ?
O14 C13 N16 . . 120.35(14) ?
O14 C13 N15 . . 120.11(15) ?
N16 C13 N15 . . 119.53(15) ?
C13 N15 H15A . . 117.9(13) ?
C13 N15 H15B . . 119.8(13) ?
H15A N15 H15B . . 120.5(19) ?
C13 N16 H16A . . 121.6(13) ?
C13 N16 H16B . . 119.7(13) ?
H16A N16 H16B . . 116.8(18) ?
C22 C21 C26 . . 121.66(15) ?
C22 C21 H21 . . 119.2 ?
C26 C21 H21 . . 119.2 ?
C23 C22 C21 . . 120.15(15) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C24 . . 120.12(16) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C23 C24 C25 . . 119.01(16) ?
C23 C24 H24 . . 120.5 ?
C25 C24 H24 . . 120.5 ?
C24 C25 C26 . . 122.63(14) ?
C24 C25 N30 . . 116.42(14) ?
C26 C25 N30 . . 120.91(13) ?
C25 C26 C21 . . 116.43(13) ?
C25 C26 C27 . . 122.19(13) ?
C21 C26 C27 . . 121.26(13) ?
O29 C27 O28 . . 124.56(14) ?
O29 C27 C26 . . 123.10(13) ?
O28 C27 C26 . . 112.33(13) ?
C27 O28 H28 . . 110.4(15) ?
O31 N30 O32 . . 123.08(15) ?
O31 N30 C25 . . 119.25(14) ?
O32 N30 C25 . . 117.58(14) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.7(2) ?
C1 C2 C3 C4 . . . . -2.3(3) ?
C2 C3 C4 C5 . . . . 0.8(2) ?
C3 C4 C5 C6 . . . . 1.3(2) ?
C3 C4 C5 N10 . . . . -175.47(14) ?
C4 C5 C6 C1 . . . . -1.9(2) ?
N10 C5 C6 C1 . . . . 174.75(13) ?
C4 C5 C6 C7 . . . . 173.48(14) ?
N10 C5 C6 C7 . . . . -9.9(2) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
C2 C1 C6 C7 . . . . -175.04(14) ?
C5 C6 C7 O9 . . . . -13.5(2) ?
C1 C6 C7 O9 . . . . 161.62(15) ?
C5 C6 C7 O8 . . . . 167.97(14) ?
C1 C6 C7 O8 . . . . -16.9(2) ?
C4 C5 N10 O12 . . . . -69.0(2) ?
C6 C5 N10 O12 . . . . 114.14(18) ?
C4 C5 N10 O11 . . . . 107.93(17) ?
C6 C5 N10 O11 . . . . -68.92(19) ?
C26 C21 C22 C23 . . . . 0.7(3) ?
C21 C22 C23 C24 . . . . -0.4(3) ?
C22 C23 C24 C25 . . . . -0.4(3) ?
C23 C24 C25 C26 . . . . 1.0(3) ?
C23 C24 C25 N30 . . . . -176.90(16) ?
C24 C25 C26 C21 . . . . -0.8(2) ?
N30 C25 C26 C21 . . . . 177.07(14) ?
C24 C25 C26 C27 . . . . 175.20(15) ?
N30 C25 C26 C27 . . . . -7.0(2) ?
C22 C21 C26 C25 . . . . -0.1(2) ?
C22 C21 C26 C27 . . . . -176.09(15) ?
C25 C26 C27 O29 . . . . -11.7(2) ?
C21 C26 C27 O29 . . . . 164.06(15) ?
C25 C26 C27 O28 . . . . 169.41(14) ?
C21 C26 C27 O28 . . . . -14.8(2) ?
C24 C25 N30 O31 . . . . -74.5(2) ?
C26 C25 N30 O31 . . . . 107.57(19) ?
C24 C25 N30 O32 . . . . 102.28(19) ?
C26 C25 N30 O32 . . . . -75.7(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O8 H8 O14 . 0.839(10) 1.798(10) 2.6307(16) 172.(2) ?
N15 H15A O9 . 0.887(9) 2.206(11) 3.065(2) 162.9(18) ?
N15 H15B O29 2_645 0.870(9) 2.542(13) 3.3170(19) 148.8(17) ?
N16 H16A O32 2_645 0.880(9) 2.130(10) 3.009(2) 177.1(19) ?
N16 H16B O29 1_545 0.882(9) 2.125(11) 2.9879(19) 165.8(18) ?
O28 H28 O14 1_565 0.839(10) 1.767(11) 2.5940(16) 168.(2) ?

####################################################################### 
# 
# 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_1I
_database_code_depnum_ccdc_archive 'CCDC 1538730'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        'Nicotinamide 4-Fluorobenzoic Acid'
_chemical_name_common            'Nicotinamide 4-Fluorobenzoic Acid Cocrystal'
_chemical_formula_moiety         'C7 H5 F O2, C6 H6 N2 O'
_chemical_formula_sum            'C13 H11 F N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         262.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.629(16)
_cell_length_b                   7.151(8)
_cell_length_c                   13.651(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.649(17)
_cell_angle_gamma                90
_cell_volume                     1199.(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1779
_cell_measurement_theta_min      2.9942
_cell_measurement_theta_max      25.3802
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6819
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_full        26.52
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2463
_reflns_number_gt                1764
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1135
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.2386P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.55296(10) 0.3637(2) 0.75247(10) 0.0501(4) Uani d . . D 1 . .
H H1 0.6134(9) 0.363(4) 0.752(2) 0.076(8) Uiso d . . D 1 . .
C C2 0.56274(13) 0.2995(3) 0.84657(13) 0.0365(4) Uani d . . . 1 . .
O O3 0.64665(9) 0.2316(2) 0.91394(10) 0.0515(4) Uani d . . . 1 . .
C C4 0.46336(12) 0.3193(2) 0.86499(13) 0.0325(4) Uani d . . . 1 . .
C C5 0.36999(13) 0.4036(3) 0.78918(14) 0.0376(4) Uani d . . . 1 . .
H H5 0.3677 0.4446 0.7236 0.045 Uiso calc U . R 1 . .
C C6 0.27986(14) 0.4277(3) 0.80989(15) 0.0425(5) Uani d . . . 1 . .
H H6 0.217 0.4842 0.759 0.051 Uiso calc U . R 1 . .
C C7 0.28591(13) 0.3661(3) 0.90750(15) 0.0417(5) Uani d . . . 1 . .
C C8 0.37621(14) 0.2812(3) 0.98470(15) 0.0459(5) Uani d . . . 1 . .
H H8 0.3775 0.2402 1.0499 0.055 Uiso calc U . R 1 . .
C C9 0.46543(13) 0.2580(3) 0.96289(14) 0.0395(4) Uani d . . . 1 . .
H H9 0.5278 0.2008 1.0142 0.047 Uiso calc U . R 1 . .
F F10 0.19724(9) 0.3898(2) 0.92806(10) 0.0639(4) Uani d . . . 1 . .
O O11 1.01981(9) 0.5685(2) 0.63124(10) 0.0485(4) Uani d . . . 1 . .
C C12 0.92905(12) 0.5001(3) 0.60724(14) 0.0345(4) Uani d . . . 1 . .
N N13 0.86965(11) 0.4276(2) 0.50992(12) 0.0460(4) Uani d . . D 1 . .
H H13A 0.8021 0.3865 0.4899 0.042(5) Uiso d . . DR 1 . .
H H13B 0.9003 0.4289 0.4643 0.043(5) Uiso d . . DR 1 . .
C C14 0.88476(12) 0.4967(2) 0.69096(13) 0.0314(4) Uani d . . . 1 . .
C C15 0.78575(13) 0.4172(3) 0.67487(14) 0.0363(4) Uani d . . . 1 . .
H H15 0.7441 0.3601 0.6085 0.044 Uiso calc U . R 1 . .
N N16 0.74733(11) 0.4188(2) 0.75020(12) 0.0412(4) Uani d . . . 1 . .
C C17 0.80806(15) 0.5019(3) 0.84493(15) 0.0452(5) Uani d . . . 1 . .
H H17 0.7821 0.5047 0.8977 0.054 Uiso calc U . R 1 . .
C C18 0.90677(15) 0.5834(3) 0.86838(15) 0.0457(5) Uani d . . . 1 . .
H H18 0.9465 0.64 0.9354 0.055 Uiso calc U . R 1 . .
C C19 0.94607(14) 0.5799(3) 0.79061(14) 0.0395(4) Uani d . . . 1 . .
H H19 1.0132 0.633 0.805 0.047 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.316(2) ?
O1 H1 . 0.826(5) ?
C2 O3 . 1.216(2) ?
C2 C4 . 1.488(3) ?
C4 C5 . 1.383(3) ?
C4 C9 . 1.395(3) ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.372(3) ?
C6 H6 . 0.93 ?
C7 F10 . 1.365(2) ?
C7 C8 . 1.368(3) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
O11 C12 . 1.235(2) ?
C12 N13 . 1.326(2) ?
C12 C14 . 1.506(2) ?
N13 H13A . 0.8891 ?
N13 H13B . 0.8883 ?
C14 C19 . 1.385(3) ?
C14 C15 . 1.391(3) ?
C15 N16 . 1.341(2) ?
C15 H15 . 0.93 ?
N16 C17 . 1.336(3) ?
C17 C18 . 1.371(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.381(3) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 108.9(17) ?
O3 C2 O1 . . 122.85(16) ?
O3 C2 C4 . . 122.50(17) ?
O1 C2 C4 . . 114.65(15) ?
C5 C4 C9 . . 118.96(16) ?
C5 C4 C2 . . 121.68(17) ?
C9 C4 C2 . . 119.32(15) ?
C4 C5 C6 . . 120.75(18) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 118.19(17) ?
C7 C6 H6 . . 120.9 ?
C5 C6 H6 . . 120.9 ?
F10 C7 C8 . . 118.58(18) ?
F10 C7 C6 . . 118.26(17) ?
C8 C7 C6 . . 123.15(17) ?
C7 C8 C9 . . 118.00(18) ?
C7 C8 H8 . . 121.0 ?
C9 C8 H8 . . 121.0 ?
C8 C9 C4 . . 120.94(16) ?
C8 C9 H9 . . 119.5 ?
C4 C9 H9 . . 119.5 ?
O11 C12 N13 . . 121.85(15) ?
O11 C12 C14 . . 119.31(16) ?
N13 C12 C14 . . 118.84(16) ?
C12 N13 H13A . . 122.6 ?
C12 N13 H13B . . 115.5 ?
H13A N13 H13B . . 121.8 ?
C19 C14 C15 . . 117.53(15) ?
C19 C14 C12 . . 117.95(16) ?
C15 C14 C12 . . 124.52(15) ?
N16 C15 C14 . . 123.34(17) ?
N16 C15 H15 . . 118.3 ?
C14 C15 H15 . . 118.3 ?
C17 N16 C15 . . 117.52(17) ?
N16 C17 C18 . . 123.34(16) ?
N16 C17 H17 . . 118.3 ?
C18 C17 H17 . . 118.3 ?
C17 C18 C19 . . 118.73(18) ?
C17 C18 H18 . . 120.6 ?
C19 C18 H18 . . 120.6 ?
C18 C19 C14 . . 119.54(18) ?
C18 C19 H19 . . 120.2 ?
C14 C19 H19 . . 120.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C2 C4 C5 . . . . 177.43(18) ?
O1 C2 C4 C5 . . . . -1.6(3) ?
O3 C2 C4 C9 . . . . -0.1(3) ?
O1 C2 C4 C9 . . . . -179.12(16) ?
C9 C4 C5 C6 . . . . 0.2(3) ?
C2 C4 C5 C6 . . . . -177.27(17) ?
C4 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 F10 . . . . 179.95(17) ?
C5 C6 C7 C8 . . . . -0.4(3) ?
F10 C7 C8 C9 . . . . -179.97(17) ?
C6 C7 C8 C9 . . . . 0.4(3) ?
C7 C8 C9 C4 . . . . -0.1(3) ?
C5 C4 C9 C8 . . . . -0.2(3) ?
C2 C4 C9 C8 . . . . 177.31(17) ?
O11 C12 C14 C19 . . . . 3.3(3) ?
N13 C12 C14 C19 . . . . -177.45(17) ?
O11 C12 C14 C15 . . . . -177.39(17) ?
N13 C12 C14 C15 . . . . 1.9(3) ?
C19 C14 C15 N16 . . . . 0.5(3) ?
C12 C14 C15 N16 . . . . -178.87(17) ?
C14 C15 N16 C17 . . . . 0.2(3) ?
C15 N16 C17 C18 . . . . -0.4(3) ?
N16 C17 C18 C19 . . . . 0.0(3) ?
C17 C18 C19 C14 . . . . 0.8(3) ?
C15 C14 C19 C18 . . . . -1.0(3) ?
C12 C14 C19 C18 . . . . 178.44(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N16 . 0.826(5) 1.880(8) 2.692(3) 167.(3) ?
C6 H6 O11 1_455 0.93 2.56 3.470(4) 165.1 ?
N13 H13A O3 4_565 0.89 2.09 2.967(3) 167.8 ?
N13 H13B O11 3_766 0.89 2.03 2.915(3) 176.2 ?
C15 H15 O3 4_565 0.93 2.49 3.401(4) 167.0 ?
C17 H17 F10 3_667 0.93 2.39 3.225(4) 148.8 ?

####################################################################### 
# 
# 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_7A
_database_code_depnum_ccdc_archive 'CCDC 1538738'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        'Benzamide 2-nitrobenzoic acid'
_chemical_name_common            '7A Benzamide + 2-Nitrobenzoic Acid'
_chemical_formula_moiety         '2(C7 H5 N O4), C7 H7 N O'
_chemical_formula_sum            'C21 H17 N3 O9'
_chemical_formula_iupac          ?
_chemical_formula_weight         455.38

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.988(3)
_cell_length_b                   11.004(5)
_cell_length_c                   12.725(6)
_cell_angle_alpha                73.939(10)
_cell_angle_beta                 75.605(10)
_cell_angle_gamma                89.042(11)
_cell_volume                     1039.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1946
_cell_measurement_theta_min      2.1916
_cell_measurement_theta_max      21.5491
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            17332
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.59
_diffrn_reflns_theta_full        26.59
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4182
_reflns_number_gt                1843
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.2499
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.934
_refine_ls_number_reflns         4182
_refine_ls_number_parameters     314
_refine_ls_number_restraints     10
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1431P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.7798(5) 0.8392(4) 0.5730(3) 0.0683(11) Uani d . . . 1 . .
C C2 0.5910(6) 0.8277(4) 0.5961(4) 0.0512(11) Uani d . . . 1 . .
C C3 0.5217(7) 0.8179(4) 0.5088(4) 0.0691(13) Uani d . . . 1 . .
H H3 0.5933 0.8116 0.4409 0.083 Uiso calc U . R 1 . .
C C4 0.3454(7) 0.8176(4) 0.5250(5) 0.0739(15) Uani d . . . 1 . .
H H4 0.2968 0.8119 0.4672 0.089 Uiso calc U . R 1 . .
C C5 0.2404(7) 0.8257(4) 0.6256(5) 0.0699(14) Uani d . . . 1 . .
H H5 0.1211 0.8265 0.6355 0.084 Uiso calc U . R 1 . .
C C6 0.3115(6) 0.8328(3) 0.7124(4) 0.0579(12) Uani d . . . 1 . .
H H6 0.2387 0.8364 0.7808 0.07 Uiso calc U . R 1 . .
C C7 0.4883(5) 0.8346(3) 0.6998(4) 0.0462(10) Uani d . . . 1 . .
C C8 0.5568(5) 0.8367(4) 0.7986(3) 0.0475(10) Uani d . . . 1 . .
O O9 0.6802(4) 0.7606(3) 0.8144(3) 0.0650(9) Uani d . . D 1 . .
H H9 0.729(7) 0.774(5) 0.869(4) 0.099(18) Uiso d . . D 1 . .
O O10 0.4958(4) 0.9021(3) 0.8601(3) 0.0700(9) Uani d . . . 1 . .
O O11 0.8422(5) 0.9227(4) 0.6005(4) 0.0906(12) Uani d . . . 1 . .
O O12 0.8643(5) 0.7694(4) 0.5243(3) 0.1065(14) Uani d . . . 1 . .
C C21 1.0864(6) 0.7856(4) 0.0805(4) 0.0542(11) Uani d . . . 1 . .
H H21 1.1156 0.7439 0.0247 0.065 Uiso calc U . R 1 . .
C C22 1.2009(6) 0.7917(4) 0.1450(4) 0.0663(13) Uani d . . . 1 . .
H H22 1.306 0.7536 0.1324 0.08 Uiso calc U . R 1 . .
C C23 1.1605(7) 0.8536(4) 0.2272(4) 0.0685(13) Uani d . . . 1 . .
H H23 1.2376 0.8575 0.2704 0.082 Uiso calc U . R 1 . .
C C24 1.0055(7) 0.9097(4) 0.2453(4) 0.0681(13) Uani d . . . 1 . .
H H24 0.9782 0.9529 0.3001 0.082 Uiso calc U . R 1 . .
C C25 0.8897(6) 0.9025(4) 0.1828(4) 0.0582(12) Uani d . . . 1 . .
H H25 0.7838 0.9392 0.1972 0.07 Uiso calc U . R 1 . .
C C26 0.9289(5) 0.8411(3) 0.0986(3) 0.0444(9) Uani d . . . 1 . .
C C27 0.8105(5) 0.8351(3) 0.0267(3) 0.0482(10) Uani d . . . 1 . .
N N28 0.6681(5) 0.8978(4) 0.0372(4) 0.0651(11) Uani d . . D 1 . .
H H28A 0.632(10) 0.935(6) 0.092(5) 0.19(3) Uiso d . . D 1 . .
H H28B 0.615(7) 0.905(5) -0.021(4) 0.10(2) Uiso d . . D 1 . .
O O29 0.8449(4) 0.7701(3) -0.0418(2) 0.0618(9) Uani d . . . 1 . .
N N31 0.5079(6) 0.5785(4) 0.3156(3) 0.0695(12) Uani d . . . 1 . .
C C32 0.6870(5) 0.5420(4) 0.2825(4) 0.0509(10) Uani d . . . 1 . .
C C33 0.7916(6) 0.5495(4) 0.3523(4) 0.0647(13) Uani d . . . 1 . .
H H33 0.7505 0.5808 0.4142 0.078 Uiso calc U . R 1 . .
C C34 0.9578(6) 0.5098(4) 0.3288(4) 0.0692(13) Uani d . . . 1 . .
H H34 1.0302 0.5145 0.3748 0.083 Uiso calc U . R 1 . .
C C35 1.0164(6) 0.4633(4) 0.2374(4) 0.0642(12) Uani d . . . 1 . .
H H35 1.1278 0.4349 0.2229 0.077 Uiso calc U . R 1 . .
C C36 0.9130(5) 0.4581(4) 0.1669(4) 0.0558(11) Uani d . . . 1 . .
H H36 0.9559 0.4274 0.1048 0.067 Uiso calc U . R 1 . .
C C37 0.7438(5) 0.4983(3) 0.1875(3) 0.0456(10) Uani d . . . 1 . .
C C38 0.6359(5) 0.4995(3) 0.1078(3) 0.0458(10) Uani d . . . 1 . .
O O39 0.6882(4) 0.4302(3) 0.0396(3) 0.0669(9) Uani d . . D 1 . .
H H39 0.624(6) 0.426(4) -0.005(4) 0.082(17) Uiso d . . D 1 . .
O O40 0.5078(4) 0.5633(3) 0.1051(3) 0.0644(9) Uani d . . . 1 . .
O O41 0.3923(5) 0.4969(5) 0.3463(4) 0.1157(16) Uani d . . . 1 . .
O O42 0.4887(5) 0.6897(4) 0.3114(4) 0.1114(14) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 O12 . 1.212(5) ?
N1 O11 . 1.222(5) ?
N1 C2 . 1.464(6) ?
C2 C3 . 1.388(6) ?
C2 C7 . 1.391(6) ?
C3 C4 . 1.372(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.370(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.382(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.381(6) ?
C6 H6 . 0.93 ?
C7 C8 . 1.496(5) ?
C8 O10 . 1.216(4) ?
C8 O9 . 1.300(4) ?
O9 H9 . 0.93(4) ?
C21 C22 . 1.386(6) ?
C21 C26 . 1.385(5) ?
C21 H21 . 0.93 ?
C22 C23 . 1.372(6) ?
C22 H22 . 0.93 ?
C23 C24 . 1.371(7) ?
C23 H23 . 0.93 ?
C24 C25 . 1.378(6) ?
C24 H24 . 0.93 ?
C25 C26 . 1.388(5) ?
C25 H25 . 0.93 ?
C26 C27 . 1.484(6) ?
C27 O29 . 1.251(4) ?
C27 N28 . 1.318(5) ?
N28 H28A . 0.89(4) ?
N28 H28B . 0.92(4) ?
N31 O41 . 1.211(5) ?
N31 O42 . 1.218(5) ?
N31 C32 . 1.470(6) ?
C32 C33 . 1.380(6) ?
C32 C37 . 1.394(5) ?
C33 C34 . 1.378(6) ?
C33 H33 . 0.93 ?
C34 C35 . 1.373(6) ?
C34 H34 . 0.93 ?
C35 C36 . 1.374(6) ?
C35 H35 . 0.93 ?
C36 C37 . 1.399(5) ?
C36 H36 . 0.93 ?
C37 C38 . 1.482(6) ?
C38 O40 . 1.234(4) ?
C38 O39 . 1.297(4) ?
O39 H39 . 0.86(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O12 N1 O11 . . 124.2(5) ?
O12 N1 C2 . . 118.4(4) ?
O11 N1 C2 . . 117.3(4) ?
C3 C2 C7 . . 122.5(4) ?
C3 C2 N1 . . 117.3(4) ?
C7 C2 N1 . . 120.1(4) ?
C4 C3 C2 . . 118.5(5) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 120.6(5) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.1(5) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 121.5(5) ?
C7 C6 H6 . . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C2 . . 116.8(4) ?
C6 C7 C8 . . 118.9(4) ?
C2 C7 C8 . . 124.2(4) ?
O10 C8 O9 . . 123.9(4) ?
O10 C8 C7 . . 121.4(3) ?
O9 C8 C7 . . 114.6(3) ?
C8 O9 H9 . . 111.(3) ?
C22 C21 C26 . . 120.5(4) ?
C22 C21 H21 . . 119.7 ?
C26 C21 H21 . . 119.7 ?
C23 C22 C21 . . 120.5(4) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 119.5(4) ?
C22 C23 H23 . . 120.3 ?
C24 C23 H23 . . 120.3 ?
C23 C24 C25 . . 120.5(4) ?
C23 C24 H24 . . 119.8 ?
C25 C24 H24 . . 119.8 ?
C24 C25 C26 . . 120.9(4) ?
C24 C25 H25 . . 119.5 ?
C26 C25 H25 . . 119.5 ?
C21 C26 C25 . . 118.1(4) ?
C21 C26 C27 . . 119.2(4) ?
C25 C26 C27 . . 122.6(4) ?
O29 C27 N28 . . 120.7(4) ?
O29 C27 C26 . . 120.3(3) ?
N28 C27 C26 . . 119.0(4) ?
C27 N28 H28A . . 123.(5) ?
C27 N28 H28B . . 114.(3) ?
H28A N28 H28B . . 123.(6) ?
O41 N31 O42 . . 125.3(5) ?
O41 N31 C32 . . 118.2(4) ?
O42 N31 C32 . . 116.4(5) ?
C33 C32 C37 . . 122.7(4) ?
C33 C32 N31 . . 116.5(4) ?
C37 C32 N31 . . 120.8(4) ?
C34 C33 C32 . . 118.9(4) ?
C34 C33 H33 . . 120.5 ?
C32 C33 H33 . . 120.5 ?
C35 C34 C33 . . 119.9(5) ?
C35 C34 H34 . . 120.1 ?
C33 C34 H34 . . 120.1 ?
C36 C35 C34 . . 121.0(4) ?
C36 C35 H35 . . 119.5 ?
C34 C35 H35 . . 119.5 ?
C35 C36 C37 . . 120.9(4) ?
C35 C36 H36 . . 119.6 ?
C37 C36 H36 . . 119.6 ?
C32 C37 C36 . . 116.6(4) ?
C32 C37 C38 . . 122.5(3) ?
C36 C37 C38 . . 120.8(4) ?
O40 C38 O39 . . 122.5(4) ?
O40 C38 C37 . . 122.6(3) ?
O39 C38 C37 . . 114.9(3) ?
C38 O39 H39 . . 116.(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O12 N1 C2 C3 . . . . -45.3(6) ?
O11 N1 C2 C3 . . . . 131.9(5) ?
O12 N1 C2 C7 . . . . 138.6(4) ?
O11 N1 C2 C7 . . . . -44.3(6) ?
C7 C2 C3 C4 . . . . 1.4(7) ?
N1 C2 C3 C4 . . . . -174.7(4) ?
C2 C3 C4 C5 . . . . -0.6(7) ?
C3 C4 C5 C6 . . . . -0.8(7) ?
C4 C5 C6 C7 . . . . 1.4(7) ?
C5 C6 C7 C2 . . . . -0.6(6) ?
C5 C6 C7 C8 . . . . -177.4(4) ?
C3 C2 C7 C6 . . . . -0.8(6) ?
N1 C2 C7 C6 . . . . 175.2(4) ?
C3 C2 C7 C8 . . . . 175.8(4) ?
N1 C2 C7 C8 . . . . -8.3(6) ?
C6 C7 C8 O10 . . . . -41.5(6) ?
C2 C7 C8 O10 . . . . 142.0(4) ?
C6 C7 C8 O9 . . . . 136.2(4) ?
C2 C7 C8 O9 . . . . -40.3(6) ?
C26 C21 C22 C23 . . . . -0.4(7) ?
C21 C22 C23 C24 . . . . 0.0(8) ?
C22 C23 C24 C25 . . . . 1.0(8) ?
C23 C24 C25 C26 . . . . -1.5(7) ?
C22 C21 C26 C25 . . . . -0.1(6) ?
C22 C21 C26 C27 . . . . 178.8(4) ?
C24 C25 C26 C21 . . . . 1.0(6) ?
C24 C25 C26 C27 . . . . -177.8(4) ?
C21 C26 C27 O29 . . . . 7.0(6) ?
C25 C26 C27 O29 . . . . -174.2(4) ?
C21 C26 C27 N28 . . . . -173.9(4) ?
C25 C26 C27 N28 . . . . 5.0(6) ?
O41 N31 C32 C33 . . . . -112.0(5) ?
O42 N31 C32 C33 . . . . 66.8(6) ?
O41 N31 C32 C37 . . . . 65.9(6) ?
O42 N31 C32 C37 . . . . -115.3(5) ?
C37 C32 C33 C34 . . . . -1.4(7) ?
N31 C32 C33 C34 . . . . 176.5(4) ?
C32 C33 C34 C35 . . . . -0.3(7) ?
C33 C34 C35 C36 . . . . 1.4(8) ?
C34 C35 C36 C37 . . . . -1.0(7) ?
C33 C32 C37 C36 . . . . 1.8(6) ?
N31 C32 C37 C36 . . . . -176.0(4) ?
C33 C32 C37 C38 . . . . -175.2(4) ?
N31 C32 C37 C38 . . . . 7.0(6) ?
C35 C36 C37 C32 . . . . -0.6(6) ?
C35 C36 C37 C38 . . . . 176.5(4) ?
C32 C37 C38 O40 . . . . 16.5(6) ?
C36 C37 C38 O40 . . . . -160.3(4) ?
C32 C37 C38 O39 . . . . -164.7(4) ?
C36 C37 C38 O39 . . . . 18.4(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O9 H9 O29 1_556 0.93(4) 1.62(4) 2.529(4) 166.(5) ?
N28 H28A O10 2_676 0.89(4) 2.20(6) 2.987(5) 147.(7) ?
N28 H28B O10 1_554 0.92(4) 1.99(4) 2.908(5) 174.(5) ?
O39 H39 O40 2_665 0.86(4) 1.83(4) 2.684(4) 174.(5) ?

####################################################################### 
# 
# 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_1C
_database_code_depnum_ccdc_archive 'CCDC 1538729'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        'Nicotinamide 2-Nitrobenzoic Acid'
_chemical_name_common            'Nicotinamide + 2Nitrobenzoic Acid'
_chemical_formula_moiety         'C7 H5 N O4, C6 H6 N2 O'
_chemical_formula_sum            'C13 H11 N3 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.25

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1167(5)
_cell_length_b                   7.5590(5)
_cell_length_c                   12.8081(9)
_cell_angle_alpha                85.164(2)
_cell_angle_beta                 75.933(2)
_cell_angle_gamma                85.895(2)
_cell_volume                     665.04(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4430
_cell_measurement_theta_min      2.7080
_cell_measurement_theta_max      25.6006
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Sealed tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'ω and θ scans'


_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            19325
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2718
_reflns_number_gt                2064
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1159
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     202
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.1530P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O8 0.7016(2) 0.12253(17) 0.62520(10) 0.0591(4) Uani d . . D 1 . .
O O28 0.17735(19) 0.60390(18) 0.88830(9) 0.0565(4) Uani d . . . 1 . .
O O9 0.7475(2) 0.3148(2) 0.73616(9) 0.0690(4) Uani d . . . 1 . .
N N29 0.1528(2) 0.6228(2) 1.06520(11) 0.0482(4) Uani d . . D 1 . .
N N10 0.7803(2) 0.8299(2) 0.31076(12) 0.0526(4) Uani d . . . 1 . .
N N22 0.6546(2) 0.90616(19) 0.79889(11) 0.0494(4) Uani d . . . 1 . .
O O12 0.8075(3) 0.9795(2) 0.33054(13) 0.0812(5) Uani d . . . 1 . .
O O11 0.7656(3) 0.7939(2) 0.22265(11) 0.0784(5) Uani d . . . 1 . .
C C6 0.7429(2) 0.4218(2) 0.55774(11) 0.0378(3) Uani d . . . 1 . .
C C26 0.4292(2) 0.74284(19) 0.93579(11) 0.0363(3) Uani d . . . 1 . .
C C3 0.7669(2) 0.6863(2) 0.39705(12) 0.0407(4) Uani d . . . 1 . .
C C27 0.2421(2) 0.6511(2) 0.96195(12) 0.0398(4) Uani d . . . 1 . .
C C25 0.5482(2) 0.7499(2) 1.00624(12) 0.0407(4) Uani d . . . 1 . .
H H25 0.5113 0.7 1.0766 0.049 Uiso calc U . R 1 . .
C C7 0.7306(2) 0.2808(2) 0.64825(12) 0.0428(4) Uani d . . . 1 . .
C C1 0.7425(2) 0.3810(2) 0.45412(12) 0.0411(4) Uani d . . . 1 . .
H H1 0.7336 0.2638 0.4397 0.049 Uiso calc U . R 1 . .
C C21 0.4890(3) 0.8235(2) 0.83253(13) 0.0439(4) Uani d . . . 1 . .
H H21 0.41 0.8196 0.7847 0.053 Uiso calc U . R 1 . .
C C2 0.7553(2) 0.5148(2) 0.37202(12) 0.0433(4) Uani d . . . 1 . .
H H2 0.7561 0.4892 0.3022 0.052 Uiso calc U . R 1 . .
C C5 0.7563(2) 0.5964(2) 0.57941(12) 0.0446(4) Uani d . . . 1 . .
H H5 0.7575 0.623 0.6488 0.053 Uiso calc U . R 1 . .
C C24 0.7220(2) 0.8317(2) 0.97091(13) 0.0465(4) Uani d . . . 1 . .
H H24 0.8052 0.8352 1.0165 0.056 Uiso calc U . R 1 . .
C C4 0.7679(3) 0.7313(2) 0.49866(13) 0.0464(4) Uani d . . . 1 . .
H H4 0.7761 0.8489 0.5126 0.056 Uiso calc U . R 1 . .
C C23 0.7699(3) 0.9079(2) 0.86688(14) 0.0495(4) Uani d . . . 1 . .
H H23 0.8872 0.9627 0.8431 0.059 Uiso calc U . R 1 . .
H H8 0.694(4) 0.052(3) 0.6802(15) 0.109(10) Uiso d . . D 1 . .
H H29A 0.048(2) 0.558(2) 1.0815(15) 0.058(5) Uiso d . . D 1 . .
H H29B 0.200(3) 0.658(2) 1.1173(12) 0.056(5) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O8 C7 . 1.298(2) ?
O8 H8 . 0.838(10) ?
O28 C27 . 1.2334(18) ?
O9 C7 . 1.2114(19) ?
N29 C27 . 1.327(2) ?
N29 H29A . 0.895(9) ?
N29 H29B . 0.883(9) ?
N10 O11 . 1.2133(19) ?
N10 O12 . 1.218(2) ?
N10 C3 . 1.474(2) ?
N22 C21 . 1.334(2) ?
N22 C23 . 1.335(2) ?
C6 C5 . 1.386(2) ?
C6 C1 . 1.388(2) ?
C6 C7 . 1.498(2) ?
C26 C25 . 1.386(2) ?
C26 C21 . 1.389(2) ?
C26 C27 . 1.497(2) ?
C3 C4 . 1.375(2) ?
C3 C2 . 1.374(2) ?
C25 C24 . 1.381(2) ?
C25 H25 . 0.93 ?
C1 C2 . 1.387(2) ?
C1 H1 . 0.93 ?
C21 H21 . 0.93 ?
C2 H2 . 0.93 ?
C5 C4 . 1.382(2) ?
C5 H5 . 0.93 ?
C24 C23 . 1.379(2) ?
C24 H24 . 0.93 ?
C4 H4 . 0.93 ?
C23 H23 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O8 H8 . . 109.4(19) ?
C27 N29 H29A . . 118.0(13) ?
C27 N29 H29B . . 121.8(13) ?
H29A N29 H29B . . 119.9(18) ?
O11 N10 O12 . . 122.75(16) ?
O11 N10 C3 . . 118.58(15) ?
O12 N10 C3 . . 118.66(15) ?
C21 N22 C23 . . 118.41(14) ?
C5 C6 C1 . . 120.06(14) ?
C5 C6 C7 . . 118.29(13) ?
C1 C6 C7 . . 121.64(14) ?
C25 C26 C21 . . 117.89(15) ?
C25 C26 C27 . . 124.77(13) ?
C21 C26 C27 . . 117.32(14) ?
C4 C3 C2 . . 123.41(15) ?
C4 C3 N10 . . 117.94(15) ?
C2 C3 N10 . . 118.64(14) ?
O28 C27 N29 . . 122.52(15) ?
O28 C27 C26 . . 119.69(13) ?
N29 C27 C26 . . 117.79(13) ?
C24 C25 C26 . . 119.34(14) ?
C24 C25 H25 . . 120.3 ?
C26 C25 H25 . . 120.3 ?
O9 C7 O8 . . 123.32(15) ?
O9 C7 C6 . . 121.35(15) ?
O8 C7 C6 . . 115.33(13) ?
C6 C1 C2 . . 120.14(15) ?
C6 C1 H1 . . 119.9 ?
C2 C1 H1 . . 119.9 ?
N22 C21 C26 . . 122.94(15) ?
N22 C21 H21 . . 118.5 ?
C26 C21 H21 . . 118.5 ?
C3 C2 C1 . . 117.97(14) ?
C3 C2 H2 . . 121.0 ?
C1 C2 H2 . . 121.0 ?
C4 C5 C6 . . 120.51(14) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C23 C24 C25 . . 118.80(15) ?
C23 C24 H24 . . 120.6 ?
C25 C24 H24 . . 120.6 ?
C3 C4 C5 . . 117.90(15) ?
C3 C4 H4 . . 121.1 ?
C5 C4 H4 . . 121.1 ?
N22 C23 C24 . . 122.58(16) ?
N22 C23 H23 . . 118.7 ?
C24 C23 H23 . . 118.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 N10 C3 C4 . . . . -174.80(17) ?
O12 N10 C3 C4 . . . . 5.9(2) ?
O11 N10 C3 C2 . . . . 5.6(2) ?
O12 N10 C3 C2 . . . . -173.68(17) ?
C25 C26 C27 O28 . . . . -157.64(16) ?
C21 C26 C27 O28 . . . . 21.0(2) ?
C25 C26 C27 N29 . . . . 22.0(2) ?
C21 C26 C27 N29 . . . . -159.41(16) ?
C21 C26 C25 C24 . . . . -1.6(2) ?
C27 C26 C25 C24 . . . . 176.97(15) ?
C5 C6 C7 O9 . . . . -5.9(2) ?
C1 C6 C7 O9 . . . . 173.66(17) ?
C5 C6 C7 O8 . . . . 174.32(15) ?
C1 C6 C7 O8 . . . . -6.1(2) ?
C5 C6 C1 C2 . . . . 0.0(2) ?
C7 C6 C1 C2 . . . . -179.60(15) ?
C23 N22 C21 C26 . . . . 1.5(3) ?
C25 C26 C21 N22 . . . . 0.1(2) ?
C27 C26 C21 N22 . . . . -178.61(15) ?
C4 C3 C2 C1 . . . . 0.5(3) ?
N10 C3 C2 C1 . . . . -179.92(14) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
C1 C6 C5 C4 . . . . 0.5(2) ?
C7 C6 C5 C4 . . . . -179.95(15) ?
C26 C25 C24 C23 . . . . 1.5(2) ?
C2 C3 C4 C5 . . . . -0.1(3) ?
N10 C3 C4 C5 . . . . -179.67(15) ?
C6 C5 C4 C3 . . . . -0.4(3) ?
C21 N22 C23 C24 . . . . -1.7(3) ?
C25 C24 C23 N22 . . . . 0.2(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O28 2_666 0.93 2.52 3.4377(19) 169.1 ?
C24 H24 O11 1_556 0.93 2.58 3.300(2) 134.5 ?
C4 H4 O8 1_565 0.93 2.57 3.439(2) 155.5 ?
O8 H8 N22 1_545 0.838(10) 1.780(10) 2.6152(17) 175.(3) ?
N29 H29A O28 2_567 0.895(9) 2.028(10) 2.9217(19) 175.6(19) ?
N29 H29B O9 2_667 0.883(9) 2.030(11) 2.8855(18) 162.6(18) ?

####################################################################### 
# 
# 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_2A
_database_code_depnum_ccdc_archive 'CCDC 1538741'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            '2Nitrobenzoic Acid + Isonicotinamide'
_chemical_formula_moiety         
'C7 H4 N O4, C7 H5 N O4, C6 H7 N2 O, C6 H6 N2 O'
_chemical_formula_sum            'C26 H22 N6 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         578.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.873(2)
_cell_length_b                   34.245(8)
_cell_length_c                   9.175(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.942(8)
_cell_angle_gamma                90
_cell_volume                     2680.7(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9096
_cell_measurement_theta_min      2.3755
_cell_measurement_theta_max      25.0211
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Brick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.570
_exptl_crystal_size_min          0.330
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200

_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            29445
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.85
_diffrn_reflns_theta_full        25.85
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.912
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             4734
_reflns_number_gt                3588
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1394
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         4734
_refine_ls_number_parameters     400
_refine_ls_number_restraints     6
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+1.0512P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5342(3) 0.56549(6) 0.9550(2) 0.0450(5) Uani d . . . 1 . .
H H1 0.5251 0.5387 0.939 0.054 Uiso calc U . R 1 . .
C C2 0.5817(3) 0.58912(6) 0.8522(3) 0.0491(5) Uani d . . . 1 . .
H H2 0.6043 0.578 0.7681 0.059 Uiso calc U . R 1 . .
N N3 0.5949(2) 0.62756(5) 0.8742(2) 0.0497(5) Uani d . . D 1 . .
H H3 0.6157 0.6416 0.7996 0.107(12) Uiso d . . DR 1 . .
C C4 0.5624(3) 0.64398(7) 0.9963(3) 0.0583(6) Uani d . . . 1 . .
H H4 0.5722 0.6709 1.009 0.07 Uiso calc U . R 1 . .
C C5 0.5150(3) 0.62210(6) 1.1034(3) 0.0539(6) Uani d . . . 1 . .
H H5 0.494 0.634 1.1867 0.065 Uiso calc U . R 1 . .
C C6 0.4998(2) 0.58191(6) 1.0829(2) 0.0396(5) Uani d . . . 1 . .
C C7 0.4409(2) 0.55631(6) 1.1914(2) 0.0421(5) Uani d . . . 1 . .
N N8 0.4661(2) 0.56823(6) 1.3375(2) 0.0520(5) Uani d . . D 1 . .
H H8A 0.527(2) 0.5882(5) 1.379(2) 0.059(7) Uiso d . . D 1 . .
H H8B 0.435(3) 0.5548(6) 1.4069(19) 0.055(7) Uiso d . . D 1 . .
O O9 0.3714(2) 0.52604(4) 1.14047(18) 0.0565(4) Uani d . . . 1 . .
C C21 0.1897(3) 0.49378(6) 0.7616(3) 0.0487(5) Uani d . . . 1 . .
H H21 0.2472 0.5165 0.7925 0.058 Uiso calc U . R 1 . .
C C22 0.1153(3) 0.47595(7) 0.8584(3) 0.0537(6) Uani d . . . 1 . .
H H22 0.1254 0.4864 0.9541 0.064 Uiso calc U . R 1 . .
N N23 0.0302(2) 0.44422(5) 0.8158(2) 0.0529(5) Uani d . . . 1 . .
C C24 0.0201(3) 0.42923(7) 0.6758(3) 0.0633(7) Uani d . . . 1 . .
H H24 -0.04 0.4068 0.6471 0.076 Uiso calc U . R 1 . .
C C25 0.0924(3) 0.44480(6) 0.5733(3) 0.0568(6) Uani d . . . 1 . .
H H25 0.0824 0.4332 0.4794 0.068 Uiso calc U . R 1 . .
C C26 0.1795(2) 0.47802(6) 0.6161(2) 0.0393(5) Uani d . . . 1 . .
C C27 0.2602(2) 0.49809(6) 0.5111(2) 0.0416(5) Uani d . . . 1 . .
N N28 0.2416(2) 0.48348(6) 0.3694(2) 0.0531(5) Uani d . . D 1 . .
H H28A 0.282(3) 0.4960(7) 0.304(2) 0.063(7) Uiso d . . D 1 . .
H H28B 0.179(3) 0.4632(5) 0.335(3) 0.074(8) Uiso d . . D 1 . .
O O29 0.3386(2) 0.52721(5) 0.55901(19) 0.0612(5) Uani d . . . 1 . .
C C31 0.8726(3) 0.67349(8) 0.4151(3) 0.0594(6) Uani d . . . 1 . .
H H31 0.9314 0.6519 0.4594 0.071 Uiso calc U . R 1 . .
C C32 0.9297(3) 0.69800(10) 0.3220(3) 0.0767(8) Uani d . . . 1 . .
H H32 1.026 0.6924 0.3052 0.092 Uiso calc U . R 1 . .
C C33 0.8490(4) 0.73008(9) 0.2544(3) 0.0789(9) Uani d . . . 1 . .
H H33 0.8887 0.7458 0.191 0.095 Uiso calc U . R 1 . .
C C34 0.7124(4) 0.73843(7) 0.2808(3) 0.0682(7) Uani d . . . 1 . .
H H34 0.6563 0.7606 0.2395 0.082 Uiso calc U . R 1 . .
C C35 0.6558(3) 0.71316(6) 0.3718(3) 0.0490(5) Uani d . . . 1 . .
C C36 0.7338(2) 0.68044(6) 0.4423(2) 0.0407(5) Uani d . . . 1 . .
C C37 0.6812(2) 0.65449(6) 0.5540(2) 0.0411(5) Uani d . . . 1 . .
O O38 0.6810(2) 0.61891(4) 0.5377(2) 0.0639(5) Uani d . . . 1 . .
O O39 0.6456(2) 0.67215(4) 0.66397(18) 0.0628(5) Uani d . . . 1 . .
N N40 0.5031(3) 0.72035(8) 0.3871(3) 0.0708(6) Uani d . . . 1 . .
O O41 0.4146(3) 0.69286(8) 0.3637(3) 0.0937(7) Uani d . . . 1 . .
O O42 0.4718(3) 0.75305(8) 0.4209(3) 0.1271(10) Uani d . . . 1 . .
C C51 0.8109(3) 0.30334(7) 0.2378(3) 0.0603(6) Uani d . . . 1 . .
H H51 0.814 0.277 0.2138 0.072 Uiso calc U . R 1 . .
C C52 0.7428(3) 0.31517(8) 0.3494(3) 0.0658(7) Uani d . . . 1 . .
H H52 0.7004 0.2966 0.4008 0.079 Uiso calc U . R 1 . .
C C53 0.7374(3) 0.35408(8) 0.3847(3) 0.0624(7) Uani d . . . 1 . .
H H53 0.6907 0.3618 0.4593 0.075 Uiso calc U . R 1 . .
C C54 0.8019(3) 0.38183(8) 0.3087(3) 0.0548(6) Uani d . . . 1 . .
H H54 0.7984 0.4081 0.3336 0.066 Uiso calc U . R 1 . .
C C55 0.8722(2) 0.37089(6) 0.1953(2) 0.0458(5) Uani d . . . 1 . .
C C56 0.8745(2) 0.33119(7) 0.1624(3) 0.0491(5) Uani d . . . 1 . .
N N57 0.9514(3) 0.31693(6) 0.0486(3) 0.0634(6) Uani d . . . 1 . .
O O58 1.0682(2) 0.33261(7) 0.0439(3) 0.0942(7) Uani d . . . 1 . .
O O59 0.8949(3) 0.28969(7) -0.0342(3) 0.1083(9) Uani d . . . 1 . .
C C60 0.9355(3) 0.40201(7) 0.1127(3) 0.0481(5) Uani d . . . 1 . .
O O61 0.8854(2) 0.40033(6) -0.0374(2) 0.0697(5) Uani d . . D 1 . .
H H61 0.928(4) 0.4170(8) -0.080(4) 0.104(12) Uiso d . . D 1 . .
O O62 1.0195(2) 0.42716(5) 0.1837(2) 0.0755(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.393(3) ?
C1 C6 . 1.408(3) ?
C1 H1 . 0.93 ?
C2 N3 . 1.332(3) ?
C2 H2 . 0.93 ?
N3 C4 . 1.353(3) ?
N3 H3 . 0.8959 ?
C4 C5 . 1.389(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.390(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.523(3) ?
C7 O9 . 1.231(2) ?
C7 N8 . 1.360(3) ?
N8 H8A . 0.889(5) ?
N8 H8B . 0.890(5) ?
C21 C22 . 1.385(3) ?
C21 C26 . 1.420(3) ?
C21 H21 . 0.93 ?
C22 N23 . 1.319(3) ?
C22 H22 . 0.93 ?
N23 C24 . 1.363(3) ?
C24 C25 . 1.383(3) ?
C24 H24 . 0.93 ?
C25 C26 . 1.371(3) ?
C25 H25 . 0.93 ?
C26 C27 . 1.514(3) ?
C27 O29 . 1.226(2) ?
C27 N28 . 1.360(3) ?
N28 H28A . 0.891(5) ?
N28 H28B . 0.889(5) ?
C31 C36 . 1.344(3) ?
C31 C32 . 1.389(4) ?
C31 H31 . 0.93 ?
C32 C33 . 1.364(4) ?
C32 H32 . 0.93 ?
C33 C34 . 1.331(4) ?
C33 H33 . 0.93 ?
C34 C35 . 1.388(3) ?
C34 H34 . 0.93 ?
C35 C36 . 1.380(3) ?
C35 N40 . 1.421(3) ?
C36 C37 . 1.524(3) ?
C37 O38 . 1.228(2) ?
C37 O39 . 1.288(3) ?
N40 O41 . 1.207(3) ?
N40 O42 . 1.214(3) ?
C51 C52 . 1.384(4) ?
C51 C56 . 1.386(3) ?
C51 H51 . 0.93 ?
C52 C53 . 1.375(4) ?
C52 H52 . 0.93 ?
C53 C54 . 1.391(3) ?
C53 H53 . 0.93 ?
C54 C55 . 1.403(3) ?
C54 H54 . 0.93 ?
C55 C56 . 1.394(3) ?
C55 C60 . 1.503(3) ?
C56 N57 . 1.479(3) ?
N57 O58 . 1.178(3) ?
N57 O59 . 1.220(3) ?
C60 O62 . 1.206(3) ?
C60 O61 . 1.327(3) ?
O61 H61 . 0.837(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.47(19) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
N3 C2 C1 . . 120.1(2) ?
N3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 N3 C4 . . 120.40(19) ?
C2 N3 H3 . . 116.2 ?
C4 N3 H3 . . 123.0 ?
N3 C4 C5 . . 122.4(2) ?
N3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
C4 C5 C6 . . 118.4(2) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 118.21(19) ?
C5 C6 C7 . . 121.30(19) ?
C1 C6 C7 . . 120.44(17) ?
O9 C7 N8 . . 123.84(19) ?
O9 C7 C6 . . 117.56(19) ?
N8 C7 C6 . . 118.59(17) ?
C7 N8 H8A . . 124.6(16) ?
C7 N8 H8B . . 123.4(15) ?
H8A N8 H8B . . 112.(2) ?
C22 C21 C26 . . 121.1(2) ?
C22 C21 H21 . . 119.4 ?
C26 C21 H21 . . 119.4 ?
N23 C22 C21 . . 120.6(2) ?
N23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C22 N23 C24 . . 118.23(19) ?
N23 C24 C25 . . 124.9(2) ?
N23 C24 H24 . . 117.5 ?
C25 C24 H24 . . 117.5 ?
C26 C25 C24 . . 117.1(2) ?
C26 C25 H25 . . 121.4 ?
C24 C25 H25 . . 121.4 ?
C25 C26 C21 . . 118.00(19) ?
C25 C26 C27 . . 121.55(19) ?
C21 C26 C27 . . 120.44(18) ?
O29 C27 N28 . . 123.36(19) ?
O29 C27 C26 . . 117.54(19) ?
N28 C27 C26 . . 119.09(18) ?
C27 N28 H28A . . 120.2(16) ?
C27 N28 H28B . . 121.7(18) ?
H28A N28 H28B . . 118.(2) ?
C36 C31 C32 . . 121.0(2) ?
C36 C31 H31 . . 119.5 ?
C32 C31 H31 . . 119.5 ?
C33 C32 C31 . . 122.2(3) ?
C33 C32 H32 . . 118.9 ?
C31 C32 H32 . . 118.9 ?
C34 C33 C32 . . 118.7(2) ?
C34 C33 H33 . . 120.6 ?
C32 C33 H33 . . 120.6 ?
C33 C34 C35 . . 118.3(2) ?
C33 C34 H34 . . 120.9 ?
C35 C34 H34 . . 120.9 ?
C36 C35 C34 . . 124.7(2) ?
C36 C35 N40 . . 117.6(2) ?
C34 C35 N40 . . 117.6(2) ?
C31 C36 C35 . . 115.1(2) ?
C31 C36 C37 . . 119.16(19) ?
C35 C36 C37 . . 125.55(19) ?
O38 C37 O39 . . 124.68(19) ?
O38 C37 C36 . . 119.16(19) ?
O39 C37 C36 . . 116.10(17) ?
O41 N40 O42 . . 125.5(3) ?
O41 N40 C35 . . 116.1(2) ?
O42 N40 C35 . . 118.4(3) ?
C52 C51 C56 . . 119.2(2) ?
C52 C51 H51 . . 120.4 ?
C56 C51 H51 . . 120.4 ?
C53 C52 C51 . . 120.6(2) ?
C53 C52 H52 . . 119.7 ?
C51 C52 H52 . . 119.7 ?
C52 C53 C54 . . 119.8(2) ?
C52 C53 H53 . . 120.1 ?
C54 C53 H53 . . 120.1 ?
C53 C54 C55 . . 121.1(2) ?
C53 C54 H54 . . 119.4 ?
C55 C54 H54 . . 119.4 ?
C56 C55 C54 . . 117.2(2) ?
C56 C55 C60 . . 123.6(2) ?
C54 C55 C60 . . 119.2(2) ?
C51 C56 C55 . . 122.1(2) ?
C51 C56 N57 . . 117.1(2) ?
C55 C56 N57 . . 120.8(2) ?
O58 N57 O59 . . 122.8(2) ?
O58 N57 C56 . . 117.1(2) ?
O59 N57 C56 . . 120.1(2) ?
O62 C60 O61 . . 124.9(2) ?
O62 C60 C55 . . 119.7(2) ?
O61 C60 C55 . . 115.31(19) ?
C60 O61 H61 . . 113.(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 N3 . . . . -0.1(3) ?
C1 C2 N3 C4 . . . . 0.1(3) ?
C2 N3 C4 C5 . . . . 0.2(4) ?
N3 C4 C5 C6 . . . . -0.4(4) ?
C4 C5 C6 C1 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . -177.0(2) ?
C2 C1 C6 C5 . . . . -0.1(3) ?
C2 C1 C6 C7 . . . . 177.27(19) ?
C5 C6 C7 O9 . . . . 151.3(2) ?
C1 C6 C7 O9 . . . . -26.1(3) ?
C5 C6 C7 N8 . . . . -28.0(3) ?
C1 C6 C7 N8 . . . . 154.7(2) ?
C26 C21 C22 N23 . . . . -1.5(4) ?
C21 C22 N23 C24 . . . . 1.2(4) ?
C22 N23 C24 C25 . . . . -0.1(4) ?
N23 C24 C25 C26 . . . . -0.6(4) ?
C24 C25 C26 C21 . . . . 0.3(3) ?
C24 C25 C26 C27 . . . . -178.4(2) ?
C22 C21 C26 C25 . . . . 0.7(3) ?
C22 C21 C26 C27 . . . . 179.4(2) ?
C25 C26 C27 O29 . . . . -178.5(2) ?
C21 C26 C27 O29 . . . . 2.8(3) ?
C25 C26 C27 N28 . . . . 2.1(3) ?
C21 C26 C27 N28 . . . . -176.6(2) ?
C36 C31 C32 C33 . . . . 0.2(5) ?
C31 C32 C33 C34 . . . . 1.1(5) ?
C32 C33 C34 C35 . . . . -2.4(4) ?
C33 C34 C35 C36 . . . . 2.5(4) ?
C33 C34 C35 N40 . . . . -174.0(3) ?
C32 C31 C36 C35 . . . . -0.2(4) ?
C32 C31 C36 C37 . . . . -175.6(2) ?
C34 C35 C36 C31 . . . . -1.2(3) ?
N40 C35 C36 C31 . . . . 175.4(2) ?
C34 C35 C36 C37 . . . . 174.0(2) ?
N40 C35 C36 C37 . . . . -9.5(3) ?
C31 C36 C37 O38 . . . . -52.4(3) ?
C35 C36 C37 O38 . . . . 132.7(2) ?
C31 C36 C37 O39 . . . . 124.9(2) ?
C35 C36 C37 O39 . . . . -50.0(3) ?
C36 C35 N40 O41 . . . . -47.8(3) ?
C34 C35 N40 O41 . . . . 129.0(3) ?
C36 C35 N40 O42 . . . . 132.7(3) ?
C34 C35 N40 O42 . . . . -50.5(4) ?
C56 C51 C52 C53 . . . . 0.3(4) ?
C51 C52 C53 C54 . . . . -0.5(4) ?
C52 C53 C54 C55 . . . . 0.4(4) ?
C53 C54 C55 C56 . . . . 0.0(3) ?
C53 C54 C55 C60 . . . . 178.0(2) ?
C52 C51 C56 C55 . . . . 0.0(4) ?
C52 C51 C56 N57 . . . . 177.6(2) ?
C54 C55 C56 C51 . . . . -0.1(3) ?
C60 C55 C56 C51 . . . . -178.1(2) ?
C54 C55 C56 N57 . . . . -177.7(2) ?
C60 C55 C56 N57 . . . . 4.4(3) ?
C51 C56 N57 O58 . . . . -140.0(3) ?
C55 C56 N57 O58 . . . . 37.7(3) ?
C51 C56 N57 O59 . . . . 39.1(3) ?
C55 C56 N57 O59 . . . . -143.2(3) ?
C56 C55 C60 O62 . . . . -133.2(2) ?
C54 C55 C60 O62 . . . . 48.9(3) ?
C56 C55 C60 O61 . . . . 50.2(3) ?
C54 C55 C60 O61 . . . . -127.7(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O61 H61 N23 1_654 0.837(10) 1.757(12) 2.583(2) 169.(4) ?
N28 H28B O62 1_455 0.889(5) 2.094(11) 2.943(3) 159.(2) ?
N28 H28A O9 1_554 0.891(5) 2.141(6) 3.032(2) 178.(2) ?
N8 H8B O29 1_556 0.890(5) 2.054(6) 2.941(2) 174.(2) ?
N8 H8A O38 1_556 0.889(5) 2.002(10) 2.846(3) 158.(2) ?
N3 H3 O39 . 0.9 1.7 2.594(2) 174.1 ?

####################################################################### 
# 
# 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_2J
_database_code_depnum_ccdc_archive 'CCDC 1538733'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'Isonicotinamide + 2-Aminobenzoic Acid'
_chemical_formula_moiety         'C6 H6 N2 O, C7 H7 N O2'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.516(5)
_cell_length_b                   10.899(4)
_cell_length_c                   9.306(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.296(12)
_cell_angle_gamma                90
_cell_volume                     1264.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    48
_cell_measurement_theta_min      2.9507
_cell_measurement_theta_max      16.8139
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              XOS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            19310
_diffrn_reflns_av_R_equivalents  0.1923
_diffrn_reflns_av_unetI/netI     0.1362
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2225
_reflns_number_gt                1007
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1847
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2536
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2225
_refine_ls_number_parameters     190
_refine_ls_number_restraints     28
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1780(4) 0.7002(3) 0.6405(4) 0.0796(17) Uani d . . . 1 . .
H H1A 0.205 0.7187 0.5616 0.096 Uiso calc U . R 1 . .
H H1B 0.1736 0.755 0.7062 0.096 Uiso calc U . R 1 . .
C C2 0.1419(4) 0.5837(4) 0.6614(4) 0.0480(13) Uani d . . . 1 . .
C C3 0.0996(4) 0.5536(4) 0.7934(4) 0.0556(14) Uani d . . . 1 . .
H H3 0.0957 0.6138 0.8636 0.067 Uiso calc U . R 1 . .
C C4 0.0648(4) 0.4378(5) 0.8187(4) 0.0611(15) Uani d . . . 1 . .
H H4 0.0376 0.42 0.906 0.073 Uiso calc U . R 1 . .
C C5 0.0692(4) 0.3463(4) 0.7162(5) 0.0627(16) Uani d . . . 1 . .
H H5 0.0445 0.2677 0.7337 0.075 Uiso calc U . R 1 . .
C C6 0.1108(4) 0.3734(4) 0.5881(4) 0.0534(14) Uani d . . . 1 . .
H H6 0.1148 0.3117 0.5198 0.064 Uiso calc U . R 1 . .
C C7 0.1469(4) 0.4903(4) 0.5577(4) 0.0436(12) Uani d . . . 1 . .
C C8 0.1958(4) 0.5146(4) 0.4210(4) 0.0468(13) Uani d . . . 1 . .
O O9 0.2177(3) 0.6166(3) 0.3790(3) 0.0637(11) Uani d . . . 1 . .
O O10 0.2132(3) 0.4140(3) 0.3479(3) 0.0712(13) Uani d . . . 1 . .
H H10 0.2337 0.4318 0.2711 0.107 Uiso d U . R 1 . .
C C11 0.6392(4) 0.6378(4) 0.1146(4) 0.0587(15) Uani d . . . 1 . .
H H11 0.6294 0.707 0.1704 0.07 Uiso calc U . R 1 . .
C C12 0.6819(4) 0.6487(4) -0.0166(4) 0.0603(15) Uani d . . . 1 . .
H H12 0.7037 0.7257 -0.0458 0.072 Uiso calc U . R 1 . .
N N13 0.6930(4) 0.5523(4) -0.1030(3) 0.0569(12) Uani d . . . 1 . .
C C14 0.6637(4) 0.4430(4) -0.0585(4) 0.0554(14) Uani d . . . 1 . .
H H14 0.6715 0.3757 -0.118 0.066 Uiso calc U . R 1 . .
C C15 0.6220(4) 0.4244(4) 0.0722(4) 0.0576(15) Uani d . . . 1 . .
H H15 0.6015 0.3465 0.0997 0.069 Uiso calc U . R 1 . .
C C16 0.6116(4) 0.5249(4) 0.1615(4) 0.0507(13) Uani d . . . 1 . .
C C17 0.5615(4) 0.5175(4) 0.3045(4) 0.0620(16) Uani d . . D 1 . .
O O18A 0.5130(6) 0.6078(6) 0.3469(7) 0.076(2) Uani d U P D 0.7 A 1
N N19A 0.5715(10) 0.4118(7) 0.3732(11) 0.082(3) Uani d U P D 0.7 A 1
H H19A 0.5433 0.402 0.4533 0.098 Uiso calc U P R 0.7 A 1
H H19B 0.6062 0.3525 0.338 0.098 Uiso calc U P R 0.7 A 1
O O18B 0.5600(15) 0.6040(13) 0.3866(17) 0.074(6) Uani d U P D 0.3 A 2
N N19B 0.534(2) 0.4058(13) 0.343(3) 0.082(9) Uani d U P D 0.3 A 2
H H19C 0.5143 0.3929 0.4274 0.098 Uiso calc U P R 0.3 A 2
H H19D 0.5357 0.346 0.2825 0.098 Uiso calc U P R 0.3 A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.368(5) ?
N1 H1A . 0.86 ?
N1 H1B . 0.86 ?
C2 C7 . 1.408(5) ?
C2 C3 . 1.420(5) ?
C3 C4 . 1.363(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.385(6) ?
C4 H4 . 0.93 ?
C5 C6 . 1.376(6) ?
C5 H5 . 0.93 ?
C6 C7 . 1.390(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.485(5) ?
C8 O9 . 1.218(5) ?
C8 O10 . 1.319(5) ?
O10 H10 . 0.8047 ?
C11 C16 . 1.360(6) ?
C11 C12 . 1.383(6) ?
C11 H11 . 0.93 ?
C12 N13 . 1.338(5) ?
C12 H12 . 0.93 ?
N13 C14 . 1.324(5) ?
C14 C15 . 1.382(6) ?
C14 H14 . 0.93 ?
C15 C16 . 1.388(6) ?
C15 H15 . 0.93 ?
C16 C17 . 1.524(5) ?
C17 O18B . 1.215(5) ?
C17 O18A . 1.240(4) ?
C17 N19A . 1.318(5) ?
C17 N19B . 1.322(5) ?
N19A H19A . 0.86 ?
N19A H19B . 0.86 ?
N19B H19C . 0.86 ?
N19B H19D . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 H1A . . 120.0 ?
C2 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
N1 C2 C7 . . 122.5(4) ?
N1 C2 C3 . . 119.5(4) ?
C7 C2 C3 . . 118.1(4) ?
C4 C3 C2 . . 120.9(4) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C3 C4 C5 . . 121.0(4) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 119.0(4) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C7 . . 122.0(4) ?
C5 C6 H6 . . 119.0 ?
C7 C6 H6 . . 119.0 ?
C6 C7 C2 . . 119.1(4) ?
C6 C7 C8 . . 120.3(4) ?
C2 C7 C8 . . 120.4(4) ?
O9 C8 O10 . . 122.7(4) ?
O9 C8 C7 . . 124.1(4) ?
O10 C8 C7 . . 113.2(3) ?
C8 O10 H10 . . 109.8 ?
C16 C11 C12 . . 119.5(4) ?
C16 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
N13 C12 C11 . . 122.2(4) ?
N13 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
C14 N13 C12 . . 118.2(4) ?
N13 C14 C15 . . 123.0(4) ?
N13 C14 H14 . . 118.5 ?
C15 C14 H14 . . 118.5 ?
C14 C15 C16 . . 118.4(4) ?
C14 C15 H15 . . 120.8 ?
C16 C15 H15 . . 120.8 ?
C11 C16 C15 . . 118.7(4) ?
C11 C16 C17 . . 117.7(4) ?
C15 C16 C17 . . 123.3(4) ?
O18A C17 N19A . . 124.5(7) ?
O18B C17 N19B . . 121.8(18) ?
O18B C17 C16 . . 122.6(10) ?
O18A C17 C16 . . 119.3(5) ?
N19A C17 C16 . . 116.2(6) ?
N19B C17 C16 . . 114.9(15) ?
C17 N19A H19A . . 120.0 ?
C17 N19A H19B . . 120.0 ?
H19A N19A H19B . . 120.0 ?
C17 N19B H19C . . 120.0 ?
C17 N19B H19D . . 120.0 ?
H19C N19B H19D . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C2 C3 C4 . . . . -178.8(5) ?
C7 C2 C3 C4 . . . . -0.2(7) ?
C2 C3 C4 C5 . . . . -0.2(8) ?
C3 C4 C5 C6 . . . . 0.8(8) ?
C4 C5 C6 C7 . . . . -1.0(8) ?
C5 C6 C7 C2 . . . . 0.6(8) ?
C5 C6 C7 C8 . . . . 177.2(5) ?
N1 C2 C7 C6 . . . . 178.6(5) ?
C3 C2 C7 C6 . . . . 0.0(7) ?
N1 C2 C7 C8 . . . . 2.0(8) ?
C3 C2 C7 C8 . . . . -176.6(4) ?
C6 C7 C8 O9 . . . . 171.0(5) ?
C2 C7 C8 O9 . . . . -12.5(8) ?
C6 C7 C8 O10 . . . . -8.7(7) ?
C2 C7 C8 O10 . . . . 167.9(4) ?
C16 C11 C12 N13 . . . . 2.9(8) ?
C11 C12 N13 C14 . . . . -1.4(8) ?
C12 N13 C14 C15 . . . . 0.2(8) ?
N13 C14 C15 C16 . . . . -0.7(8) ?
C12 C11 C16 C15 . . . . -3.3(8) ?
C12 C11 C16 C17 . . . . -178.1(5) ?
C14 C15 C16 C11 . . . . 2.2(8) ?
C14 C15 C16 C17 . . . . 176.7(5) ?
C11 C16 C17 O18B . . . . -11.0(13) ?
C15 C16 C17 O18B . . . . 174.4(12) ?
C11 C16 C17 O18A . . . . 25.6(9) ?
C15 C16 C17 O18A . . . . -148.9(7) ?
C11 C16 C17 N19A . . . . -155.9(7) ?
C15 C16 C17 N19A . . . . 29.6(10) ?
C11 C16 C17 N19B . . . . 178.4(13) ?
C15 C16 C17 N19B . . . . 3.9(15) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1B O9 4_576 0.86 2.16 2.993(4) 161.6 ?
N1 H1A O9 . 0.86 2.05 2.688(4) 130.3 ?
O10 H10 N13 3_665 0.80 1.89 2.683(4) 166.9 ?
N19A H19A O18A 3_666 0.86 2.05 2.907(13) 174.1 ?
N19B H19C O18B 3_666 0.86 2.04 2.88(4) 165.5 ?

