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

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

data_INH_ADIP_2
_database_code_depnum_ccdc_archive 'CCDC 1422395'
_audit_update_record             
;
2015-09-04 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
#=============================================================================

_audit_creation_method           EXPO2014

_chemical_name_systematic        'isoniazid-adipic acid cocrystal II'
_chemical_formula_moiety         'C6 H10 O4, 2(C6 H7 N3 O)'
_chemical_formula_sum            'C18 H24 N6 O6 '
_chemical_formula_weight         420.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_length_a                   16.200(10)
_cell_length_b                   7.378(7)
_cell_length_c                   8.793(6)
_cell_angle_alpha                90.000
_cell_angle_beta                 105.079(30)
_cell_angle_gamma                90.000
_cell_volume                     1014.8(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  'Gobel mirror'
_diffrn_measurement_device_type  'Bruker D8'

_pd_spec_mounting                capillary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  white

_pd_meas_number_of_points        6407
_pd_meas_2theta_range_min        4.50000
_pd_meas_2theta_range_max        70.00135
_pd_meas_2theta_range_inc        0.010225
_pd_meas_scan_method             step

_pd_proc_ls_profile_function     'Pearson VII'
_pd_proc_ls_background_function  'Chebyshev polynomial of degree 20'

_pd_proc_ls_prof_R_factor        0.04334
_pd_proc_ls_prof_wR_factor       0.05947
_pd_proc_ls_prof_wR_expected     0.00752

_refine_ls_goodness_of_fit_all   7.90
_refine_ls_restrained_S_all      ?
_refine_ls_shift/su_max          ?
_refine_ls_shift/su_mean         ?

_refine_ls_R_factor_all          none


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_hall  '-P 2ybc'

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

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_occupancy
_atom_site_adp_type
C C1 .11647(20) .1679(5) .6746(5) 0.0306 1 Uiso
C C2 .03904(10) .25507(20) .56182(20) 0.0306 1 Uiso
H H1 0.0359 0.2059 0.4458 0.03672 1 Uiso
H H2 -0.0184 0.2043 0.5878 0.03672 1 Uiso
C C3 .03865(10) .46321(30) .56284(20) 0.0306 1 Uiso
H H3 0.0358 0.513 0.6784 0.03672 1 Uiso
H H4 0.0974 0.5151 0.5395 0.03672 1 Uiso
O O1 .1024(8) .0049(20) .7120(30) 0.0306 1 Uiso
O O2 .1840(8) .2517(20) .7342(30) 0.0306 1 Uiso
H H5 0.151 -0.0483 0.7868 0.03672 1 Uiso
C C4 .3383(5) -.1229(3) .6255(9) 0.0306 1 Uiso
C C5 .2728(20) -.04503(20) .5084(3) 0.0306 1 Uiso
H H6 0.266301 0.100601 0.4953 0.03672 1 Uiso
C C6 .21670(10) -.15931(30) .40480(20) 0.0306 1 Uiso
H H7 0.166501 -0.103099 0.3129 0.03672 1 Uiso
C C7 .2851(9) -.41570(30) .53000(20) 0.0306 1 Uiso
H H8 0.286501 -0.560999 0.5375 0.03672 1 Uiso
C C8 .34450(20) -.31032(30) .63750(30) 0.03672 1 Uiso
H H9 0.395301 -0.373399 0.7268 0.03672 1 Uiso
C C9 .40111(30) -.0073(7) .7426(9) 0.0306 1 Uiso
N N1 .36915(10) .1415(5) .7958(5) 0.0306 1 Uiso
N N2 .2197(10) -.3392(4) .4227(20) 0.0306 1 Uiso
N N3 .42015(10) .25839(30) .90891(30) 0.0306 1 Uiso
O O3 .4770(6) -.0559(30) .7901(30) 0.0306 1 Uiso
H H10 0.305901 0.170201 0.7634 0.03672 1 Uiso
H H11 0.456001 0.332701 0.8551 0.03672 1 Uiso
H H12 0.459501 0.182501 0.992 0.03672 1 Uiso



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . . 1.525(4)
C1 O1 . . 1.282(16)
C1 O2 . . 1.248(18)
C2 H1 . . 1.078
C2 H2 . . 1.085
C2 C3 . . 1.535(3)
C3 H3 . . 1.097
C3 H4 . . 1.101
O1 H5 . . .968
C4 C5 . . 1.39(2)
C4 C8 . . 1.388(3)
C4 C9 . . 1.509(9)
C5 H6 . . 1.077
C5 C6 . . 1.393(16)
C6 H7 . . 1.079
C6 N2 . . 1.336(4)
C7 H8 . . 1.080
C7 C8 . . 1.397(8)
C7 N2 . . 1.345(18)
C8 H9 . . 1.078
C9 N1 . . 1.348(7)
C9 O3 . . 1.244(16)
N1 N3 . . 1.410(5)
N1 H10 . . 1.009
N3 H11 . . 1.002
N3 H12 . . 1.009

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_2
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 O1 . . . 113.0(9)
C2 C1 O2 . . . 123.1(9)
C1 C2 H1 . . . 107.7
C1 C2 H2 . . . 108.6
C1 C2 C3 . . . 114.97(19)
O1 C1 O2 . . . 123.7(13)
C1 O1 H5 . . . 113.0
H1 C2 H2 . . . 104.4
H1 C2 C3 . . . 110.4
H2 C2 C3 . . . 110.1
C2 C3 H3 . . . 109.8
C2 C3 H4 . . . 109.8
H3 C3 H4 . . . 107.3
C5 C4 C8 . . . 119.5(6)
C5 C4 C9 . . . 121.2(4)
C4 C5 H6 . . . 121.5
C4 C5 C6 . . . 118.4(3)
C8 C4 C9 . . . 119.2(6)
C4 C8 C7 . . . 118.7(4)
C4 C8 H9 . . . 120.7
C4 C9 N1 . . . 116.5(5)
C4 C9 O3 . . . 119.8(12)
H6 C5 C6 . . . 120.1
C5 C6 H7 . . . 119.9
C5 C6 N2 . . . 121.7(8)
H7 C6 N2 . . . 117.6
C6 N2 C7 . . . 119.9(11)
H8 C7 C8 . . . 120.9
H8 C7 N2 . . . 118.0
C8 C7 N2 . . . 121.2(4)
C7 C8 H9 . . . 120.5
N1 C9 O3 . . . 123.6(12)
C9 N1 N3 . . . 122.4(3)
C9 N1 H10 . . . 121.7
N3 N1 H10 . . . 115.7
N1 N3 H11 . . . 107.8
N1 N3 H12 . . . 108.4
H11 N3 H12 . . . 108.1

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 H1 . . . . -80.00
O1 C1 C2 H2 . . . . 33.8
O1 C1 C2 C3 . . . . 157.3(11)
O2 C1 C2 H1 . . . . 105.8
O2 C1 C2 H2 . . . . -141.7
O2 C1 C2 C3 . . . . -17.2(13)
C2 C1 O1 H5 . . . . -178.0
O2 C1 O1 H5 . . . . -2.5
C1 C2 C3 H3 . . . . -62.7
C1 C2 C3 H4 . . . . 55.0
H1 C2 C3 H3 . . . . 175.2
H1 C2 C3 H4 . . . . -67.1
H2 C2 C3 H3 . . . . 60.4
H2 C2 C3 H4 . . . . 178.1
C8 C4 C5 H6 . . . . -180.0
C8 C4 C5 C6 . . . . -1(2)
C9 C4 C5 H6 . . . . 1.5
C9 C4 C5 C6 . . . . -179.5(12)
C5 C4 C8 C7 . . . . 0.6(16)
C5 C4 C8 H9 . . . . 179.0
C9 C4 C8 C7 . . . . 178.9(7)
C9 C4 C8 H9 . . . . -2.8
C5 C4 C9 N1 . . . . 38.8(15)
C5 C4 C9 O3 . . . . -144.3(18)
C8 C4 C9 N1 . . . . -139.5(6)
C8 C4 C9 O3 . . . . 37.4(15)
C4 C5 C6 H7 . . . . -179.0
C4 C5 C6 N2 . . . . 6(3)
H6 C5 C6 H7 . . . . -1.0
H6 C5 C6 N2 . . . . -176.1
C5 C6 N2 C7 . . . . -9(2)
H7 C6 N2 C7 . . . . 175.7
H8 C7 C8 C4 . . . . -178.0
H8 C7 C8 H9 . . . . 3.0
N2 C7 C8 C4 . . . . -4.3(15)
N2 C7 C8 H9 . . . . 177.5
H8 C7 N2 C6 . . . . -177.0
C8 C7 N2 C6 . . . . 9(2)
C4 C9 N1 N3 . . . . 178.1(4)
C4 C9 N1 H10 . . . . 3.6
O3 C9 N1 N3 . . . . 1.4(15)
O3 C9 N1 H10 . . . . -173.9
C9 N1 N3 H11 . . . . 75.8
C9 N1 N3 H12 . . . . -41.0
H10 N1 N3 H11 . . . . -109.9
H10 N1 N3 H12 . . . . 133.4
_chemical_melting_point          137
_exptl_crystal_recrystallization_method 'From the Melt'
