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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1946812'
loop_
_audit_author_name
_audit_author_address
'Anilkumar Gunnam'
;School of Chemistry, University of Hyderabad
India
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Nitrofurantoin ferulic acid cocrystal'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N4 O9'
_chemical_formula_weight         432.35

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0708(6)
_cell_length_b                   9.0071(7)
_cell_length_c                   15.9404(13)
_cell_angle_alpha                98.578(4)
_cell_angle_beta                 99.700(3)
_cell_angle_gamma                106.580(4)
_cell_volume                     937.95(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.16

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18066
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3312
_reflns_number_gt                2867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3312
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 1.24780(15) 0.43296(12) 0.59413(7) 0.0451(3) Uani 1 1 d . . . . .
O3 O 1.46029(15) 1.14207(11) 0.94859(6) 0.0371(3) Uani 1 1 d . . . . .
O4 O 1.77500(15) 0.78641(13) 0.79819(7) 0.0461(3) Uani 1 1 d . . . . .
O9 O 0.87081(17) 0.29813(13) 0.50895(7) 0.0463(3) Uani 1 1 d . . . . .
O6 O -0.29475(16) -0.25745(14) 0.24465(8) 0.0487(3) Uani 1 1 d . . . . .
O7 O 0.02732(15) -0.31463(13) 0.20269(7) 0.0466(3) Uani 1 1 d . . . . .
O8 O 0.78289(15) 0.44804(13) 0.60884(7) 0.0487(3) Uani 1 1 d . . . . .
O1 O 1.53086(19) 1.47660(13) 1.10336(7) 0.0568(3) Uani 1 1 d . . . . .
N4 N 1.53994(18) 0.58913(14) 0.68928(8) 0.0359(3) Uani 1 1 d . . . . .
N3 N 1.43223(17) 0.75958(14) 0.76641(8) 0.0368(3) Uani 1 1 d . . . . .
O2 O 1.74825(19) 1.37709(16) 1.05489(9) 0.0644(4) Uani 1 1 d . . . . .
N2 N 1.44503(18) 0.88517(13) 0.82866(7) 0.0352(3) Uani 1 1 d . . . . .
N1 N 1.5755(2) 1.37540(15) 1.05617(8) 0.0441(3) Uani 1 1 d . . . . .
C12 C 0.2542(2) -0.09133(16) 0.31681(9) 0.0343(3) Uani 1 1 d . . . . .
H12 H 0.369959 -0.108314 0.302965 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2733(2) 0.03258(16) 0.38517(9) 0.0332(3) Uani 1 1 d . . . . .
C8 C 1.3385(2) 0.54160(16) 0.65599(9) 0.0335(3) Uani 1 1 d . . . . .
C6 C 1.6044(2) 0.72127(16) 0.75696(9) 0.0338(3) Uani 1 1 d . . . . .
C5 C 1.2780(2) 0.90759(17) 0.83786(9) 0.0359(3) Uani 1 1 d . . . . .
H5 H 1.156190 0.838870 0.803053 0.043 Uiso 1 1 calc R U . . .
C16 C 0.4747(2) 0.13027(16) 0.43408(9) 0.0341(3) Uani 1 1 d . . . . .
H16 H 0.581909 0.103785 0.416492 0.041 Uiso 1 1 calc R U . . .
C9 C 1.2504(2) 0.64683(16) 0.70791(9) 0.0354(3) Uani 1 1 d . . . . .
H9A H 1.178343 0.698990 0.671177 0.042 Uiso 1 1 calc R U . . .
H9B H 1.159970 0.588296 0.739754 0.042 Uiso 1 1 calc R U . . .
C10 C -0.1074(2) -0.16328(17) 0.29013(10) 0.0365(3) Uani 1 1 d . . . . .
C1 C 1.2780(2) 1.03843(16) 0.90170(9) 0.0349(3) Uani 1 1 d . . . . .
C4 C 1.4110(2) 1.25107(16) 1.00060(9) 0.0365(3) Uani 1 1 d . . . . .
C11 C 0.0664(2) -0.18887(16) 0.26954(9) 0.0333(3) Uani 1 1 d . . . . .
C2 C 1.1233(2) 1.08325(17) 0.92503(10) 0.0394(3) Uani 1 1 d . . . . .
H2 H 0.985816 1.031868 0.902435 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7340(2) 0.34158(17) 0.54464(9) 0.0358(3) Uani 1 1 d . . . . .
C3 C 1.2109(2) 1.22219(17) 0.98988(10) 0.0418(4) Uani 1 1 d . . . . .
H3 H 1.144242 1.281317 1.019057 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0980(2) 0.05551(19) 0.40466(10) 0.0440(4) Uani 1 1 d . . . . .
H14 H 0.107474 0.137371 0.449886 0.053 Uiso 1 1 calc R U . . .
C17 C 0.5249(2) 0.25204(18) 0.50042(10) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.421748 0.282082 0.519849 0.048 Uiso 1 1 calc R U . . .
C15 C -0.0892(2) -0.0417(2) 0.35771(11) 0.0476(4) Uani 1 1 d . . . . .
H15 H -0.205032 -0.025132 0.371734 0.057 Uiso 1 1 calc R U . . .
C19 C 0.1940(3) -0.3402(2) 0.17098(13) 0.0648(6) Uani 1 1 d . . . . .
H19A H 0.146241 -0.431820 0.124293 0.097 Uiso 1 1 calc R U . . .
H19B H 0.261483 -0.249260 0.150087 0.097 Uiso 1 1 calc R U . . .
H19C H 0.286940 -0.356882 0.217120 0.097 Uiso 1 1 calc R U . . .
H8A H 0.995(4) 0.350(3) 0.5403(15) 0.078(7) Uiso 1 1 d . . . . .
H6A H -0.278(4) -0.325(3) 0.2023(17) 0.097(9) Uiso 1 1 d . . . . .
H4A H 1.626(3) 0.542(2) 0.6649(11) 0.051(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C8 1.2175(17) . ?
O3 C4 1.3501(17) . ?
O3 C1 1.3684(17) . ?
O4 C6 1.2023(17) . ?
O9 C18 1.3218(17) . ?
O9 H8A 0.89(2) . ?
O6 C10 1.3605(17) . ?
O6 H6A 0.88(3) . ?
O7 C11 1.3628(17) . ?
O7 C19 1.4210(19) . ?
O8 C18 1.2187(17) . ?
O1 N1 1.2392(18) . ?
N4 C8 1.3501(18) . ?
N4 C6 1.3893(18) . ?
N4 H4A 0.938(19) . ?
N3 N2 1.3597(16) . ?
N3 C6 1.3818(18) . ?
N3 C9 1.4570(17) . ?
O2 N1 1.2212(19) . ?
N2 C5 1.2818(19) . ?
N1 C4 1.4160(19) . ?
C12 C11 1.3792(19) . ?
C12 C13 1.3974(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(2) . ?
C13 C16 1.4548(19) . ?
C8 C9 1.500(2) . ?
C5 C1 1.438(2) . ?
C5 H5 0.9300 . ?
C16 C17 1.324(2) . ?
C16 H16 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.377(2) . ?
C10 C11 1.395(2) . ?
C1 C2 1.357(2) . ?
C4 C3 1.339(2) . ?
C2 C3 1.405(2) . ?
C2 H2 0.9300 . ?
C18 C17 1.460(2) . ?
C3 H3 0.9300 . ?
C14 C15 1.374(2) . ?
C14 H14 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O3 C1 104.32(11) . . ?
C18 O9 H8A 111.1(14) . . ?
C10 O6 H6A 107.4(17) . . ?
C11 O7 C19 117.80(12) . . ?
C8 N4 C6 112.87(12) . . ?
C8 N4 H4A 122.4(11) . . ?
C6 N4 H4A 124.5(11) . . ?
N2 N3 C6 119.96(11) . . ?
N2 N3 C9 127.73(11) . . ?
C6 N3 C9 112.20(11) . . ?
C5 N2 N3 116.72(12) . . ?
O2 N1 O1 124.54(13) . . ?
O2 N1 C4 119.35(14) . . ?
O1 N1 C4 116.11(14) . . ?
C11 C12 C13 121.09(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.38(13) . . ?
C14 C13 C16 122.64(13) . . ?
C12 C13 C16 118.97(12) . . ?
O5 C8 N4 125.11(14) . . ?
O5 C8 C9 126.98(13) . . ?
N4 C8 C9 107.91(11) . . ?
O4 C6 N3 128.09(13) . . ?
O4 C6 N4 126.36(13) . . ?
N3 C6 N4 105.55(11) . . ?
N2 C5 C1 120.34(13) . . ?
N2 C5 H5 119.8 . . ?
C1 C5 H5 119.8 . . ?
C17 C16 C13 128.29(14) . . ?
C17 C16 H16 115.9 . . ?
C13 C16 H16 115.9 . . ?
N3 C9 C8 101.27(11) . . ?
N3 C9 H9A 111.5 . . ?
C8 C9 H9A 111.5 . . ?
N3 C9 H9B 111.5 . . ?
C8 C9 H9B 111.5 . . ?
H9A C9 H9B 109.3 . . ?
O6 C10 C15 119.58(13) . . ?
O6 C10 C11 120.86(13) . . ?
C15 C10 C11 119.56(13) . . ?
C2 C1 O3 110.56(12) . . ?
C2 C1 C5 131.13(13) . . ?
O3 C1 C5 118.30(13) . . ?
C3 C4 O3 113.18(12) . . ?
C3 C4 N1 130.92(14) . . ?
O3 C4 N1 115.90(13) . . ?
O7 C11 C12 126.80(13) . . ?
O7 C11 C10 113.69(12) . . ?
C12 C11 C10 119.51(13) . . ?
C1 C2 C3 106.84(14) . . ?
C1 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
O8 C18 O9 121.51(13) . . ?
O8 C18 C17 124.25(13) . . ?
O9 C18 C17 114.24(12) . . ?
C4 C3 C2 105.10(14) . . ?
C4 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
C15 C14 C13 120.60(14) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C17 C18 123.33(14) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C10 C15 C14 120.87(14) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048

