# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Srinivasulu Aitipamula'
_publ_contact_author_email       'SRINIVASULU AITIPAMULA@ICES.A-STAR.EDU.SG'

_publ_section_title              
;
Trimorphs of a pharmaceutical cocrystal involving
two active pharmaceutical ingredients: potential relevance to combination drugs
;
loop_
_publ_author_name
'Srinivasulu Aitipamula'
'Pui Shan Chow.'
'Reginald B. H. Tan'

# Attachment 'B904616J_CIF.txt'

data_Form-I
_database_code_depnum_ccdc_archive 'CCDC 719453'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'Form I of 1:1 cocrystal of ethenzamide and gentisic acid'
;
_chemical_name_common            
"'Form I of 1:1 cocrystal of ethenzamide and gentisic acid'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O2, C7 H6 O4'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.0485(16)
_cell_length_b                   9.1139(18)
_cell_length_c                   22.607(5)
_cell_angle_alpha                94.13(3)
_cell_angle_beta                 91.52(3)
_cell_angle_gamma                113.94(3)
_cell_volume                     1508.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4264
_cell_measurement_theta_min      1.8096
_cell_measurement_theta_max      30.9526

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23198
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.28
_reflns_number_total             7419
_reflns_number_gt                6051
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0952P)²+0.4534P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7419
_refine_ls_number_parameters     457
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1918
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4A O 0.9956(2) 0.80295(19) 0.74111(7) 0.0288(4) Uani 1 1 d . . .
O5A O 0.4391(2) 0.9464(2) 0.87567(7) 0.0320(4) Uani 1 1 d . . .
O3A O 0.2963(2) 0.6912(2) 0.80326(8) 0.0315(4) Uani 1 1 d . . .
O6A O 0.7415(2) 1.08292(19) 0.88458(8) 0.0334(4) Uani 1 1 d D . .
C10A C 0.6209(3) 0.8549(2) 0.81487(9) 0.0235(4) Uani 1 1 d . . .
C15A C 0.7956(3) 0.8816(3) 0.79772(9) 0.0243(4) Uani 1 1 d . . .
H15A H 0.8951 0.9723 0.8141 0.029 Uiso 1 1 calc R . .
C12A C 0.4979(3) 0.6112(3) 0.74834(10) 0.0272(5) Uani 1 1 d . . .
H12A H 0.3988 0.5205 0.7317 0.033 Uiso 1 1 calc R . .
C13A C 0.6712(3) 0.6374(3) 0.73248(10) 0.0257(4) Uani 1 1 d . . .
H13A H 0.6883 0.5635 0.7055 0.031 Uiso 1 1 calc R . .
C14A C 0.8216(3) 0.7742(3) 0.75652(10) 0.0242(4) Uani 1 1 d . . .
C16A C 0.5934(3) 0.9664(3) 0.86075(10) 0.0260(4) Uani 1 1 d . . .
C11A C 0.4707(3) 0.7201(3) 0.78928(10) 0.0247(4) Uani 1 1 d . . .
H10A H 0.995(4) 0.734(4) 0.7072(15) 0.055(9) Uiso 1 1 d . . .
H7A H 0.308(4) 0.775(4) 0.8340(15) 0.061(9) Uiso 1 1 d . . .
H11A H 0.724(6) 1.150(5) 0.9143(15) 0.103(15) Uiso 1 1 d D . .
O1B O 0.7294(2) 0.60952(19) 0.47990(7) 0.0309(4) Uani 1 1 d . . .
O2B O 0.9781(2) 0.6147(2) 0.64456(7) 0.0346(4) Uani 1 1 d . . .
C1B C 0.8257(3) 0.4785(3) 0.55270(10) 0.0263(5) Uani 1 1 d . . .
N1B N 0.8595(3) 0.7489(3) 0.58901(11) 0.0352(5) Uani 1 1 d . . .
C6B C 0.8423(3) 0.3403(3) 0.56887(10) 0.0298(5) Uani 1 1 d . . .
H6B H 0.8936 0.3418 0.6064 0.036 Uiso 1 1 calc R . .
C7B C 0.8944(3) 0.6211(3) 0.59838(10) 0.0280(5) Uani 1 1 d . . .
C2B C 0.7475(3) 0.4741(3) 0.49567(10) 0.0272(5) Uani 1 1 d . . .
C3B C 0.6922(3) 0.3346(3) 0.45719(11) 0.0314(5) Uani 1 1 d . . .
H3B H 0.6428 0.3323 0.4193 0.038 Uiso 1 1 calc R . .
C5B C 0.7846(3) 0.2003(3) 0.53067(11) 0.0324(5) Uani 1 1 d . . .
H5B H 0.7959 0.1090 0.5426 0.039 Uiso 1 1 calc R . .
C4B C 0.7102(3) 0.1986(3) 0.47485(11) 0.0328(5) Uani 1 1 d . . .
H4B H 0.6718 0.1058 0.4488 0.039 Uiso 1 1 calc R . .
C8B C 0.6695(3) 0.6133(3) 0.41987(11) 0.0353(5) Uani 1 1 d . . .
H8AA H 0.5470 0.5313 0.4109 0.042 Uiso 1 1 calc R . .
H8BA H 0.7498 0.5931 0.3923 0.042 Uiso 1 1 calc R . .
C9B C 0.6733(4) 0.7779(3) 0.41461(14) 0.0457(7) Uani 1 1 d . . .
H9AA H 0.5924 0.7959 0.4418 0.069 Uiso 1 1 calc R . .
H9CA H 0.6351 0.7851 0.3747 0.069 Uiso 1 1 calc R . .
H9BA H 0.7949 0.8579 0.4240 0.069 Uiso 1 1 calc R . .
H1B H 0.806(4) 0.754(3) 0.5555(13) 0.030(7) Uiso 1 1 d . . .
H2B H 0.898(4) 0.835(4) 0.6154(15) 0.056(9) Uiso 1 1 d . . .
O3B O 0.9077(2) 1.0598(2) 0.65842(7) 0.0312(4) Uani 1 1 d . . .
O5B O 1.0910(2) 1.3333(2) 0.71653(8) 0.0353(4) Uani 1 1 d . . .
O4B O 0.2918(2) 1.0948(2) 0.74951(8) 0.0366(4) Uani 1 1 d . . .
C10B C 0.7704(3) 1.2047(2) 0.72079(10) 0.0242(4) Uani 1 1 d . . .
O6B O 0.9535(2) 1.45188(19) 0.77582(7) 0.0318(4) Uani 1 1 d . . .
C11B C 0.7588(3) 1.0728(3) 0.68180(10) 0.0243(4) Uani 1 1 d . . .
C15B C 0.6112(3) 1.2076(3) 0.74341(10) 0.0264(5) Uani 1 1 d . . .
H15B H 0.6186 1.2940 0.7695 0.032 Uiso 1 1 calc R . .
C16B C 0.9512(3) 1.3344(3) 0.73719(10) 0.0267(5) Uani 1 1 d . . .
C13B C 0.4332(3) 0.9537(3) 0.68816(10) 0.0272(5) Uani 1 1 d . . .
H13B H 0.3207 0.8702 0.6769 0.033 Uiso 1 1 calc R . .
C12B C 0.5893(3) 0.9491(3) 0.66619(10) 0.0272(5) Uani 1 1 d . . .
H12B H 0.5810 0.8617 0.6405 0.033 Uiso 1 1 calc R . .
C14B C 0.4432(3) 1.0833(3) 0.72733(10) 0.0262(5) Uani 1 1 d . . .
H10B H 0.192(4) 0.996(4) 0.7449(14) 0.050(9) Uiso 1 1 d . . .
H7B H 1.008(5) 1.155(5) 0.6748(16) 0.072(11) Uiso 1 1 d . . .
H11B H 1.072(5) 1.528(5) 0.7825(18) 0.082(12) Uiso 1 1 d . . .
C7A C 0.5898(3) 1.2688(3) 0.99422(10) 0.0263(5) Uani 1 1 d . . .
C4A C 0.6828(3) 1.6530(3) 1.12952(11) 0.0337(5) Uani 1 1 d . . .
H4A H 0.7058 1.7385 1.1582 0.040 Uiso 1 1 calc R . .
C5A C 0.8263(3) 1.6376(3) 1.10131(11) 0.0336(5) Uani 1 1 d . . .
H5A H 0.9454 1.7111 1.1113 0.040 Uiso 1 1 calc R . .
C9A C -0.0227(3) 1.1721(3) 1.06107(12) 0.0379(6) Uani 1 1 d . . .
H9AB H -0.0147 1.0771 1.0741 0.057 Uiso 1 1 calc R . .
H9CB H -0.0315 1.1645 1.0184 0.057 Uiso 1 1 calc R . .
H9BB H -0.1287 1.1816 1.0761 0.057 Uiso 1 1 calc R . .
H1A H 0.335(4) 1.143(4) 1.0019(14) 0.048(8) Uiso 1 1 d . . .
H2A H 0.414(4) 1.076(3) 0.9510(13) 0.035(7) Uiso 1 1 d . . .
O1A O 0.2977(2) 1.29748(19) 1.05957(7) 0.0293(4) Uani 1 1 d . . .
O2A O 0.7255(2) 1.27856(19) 0.96591(7) 0.0319(4) Uani 1 1 d . . .
N1A N 0.4284(3) 1.1466(2) 0.98245(10) 0.0324(5) Uani 1 1 d . . .
C1A C 0.6137(3) 1.3972(3) 1.04310(10) 0.0246(4) Uani 1 1 d . . .
C2A C 0.4699(3) 1.4131(3) 1.07318(10) 0.0263(5) Uani 1 1 d . . .
C8A C 0.1456(3) 1.3189(3) 1.08415(11) 0.0312(5) Uani 1 1 d . . .
H8BB H 0.1389 1.4161 1.0717 0.037 Uiso 1 1 calc R . .
H8AB H 0.1572 1.3274 1.1272 0.037 Uiso 1 1 calc R . .
C3A C 0.5054(3) 1.5422(3) 1.11551(10) 0.0307(5) Uani 1 1 d . . .
H3A H 0.4098 1.5543 1.1344 0.037 Uiso 1 1 calc R . .
C6A C 0.7900(3) 1.5110(3) 1.05787(10) 0.0285(5) Uani 1 1 d . . .
H6A H 0.8860 1.5022 1.0382 0.034 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4A C14A 1.376(2) . ?
O4A H10A 0.95(3) . ?
O5A C16A 1.240(3) . ?
O3A C11A 1.369(3) . ?
O3A H7A 0.97(3) . ?
O6A C16A 1.302(3) . ?
O6A H11A 0.929(19) . ?
C10A C15A 1.396(3) . ?
C10A C11A 1.400(3) . ?
C10A C16A 1.483(3) . ?
C15A C14A 1.384(3) . ?
C15A H15A 0.9300 . ?
C12A C13A 1.378(3) . ?
C12A C11A 1.395(3) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.399(3) . ?
C13A H13A 0.9300 . ?
O1B C2B 1.371(3) . ?
O1B C8B 1.435(3) . ?
O2B C7B 1.245(3) . ?
C1B C6B 1.392(3) . ?
C1B C2B 1.410(3) . ?
C1B C7B 1.502(3) . ?
N1B C7B 1.333(3) . ?
N1B H1B 0.87(3) . ?
N1B H2B 0.89(3) . ?
C6B C5B 1.389(3) . ?
C6B H6B 0.9300 . ?
C2B C3B 1.390(3) . ?
C3B C4B 1.389(3) . ?
C3B H3B 0.9300 . ?
C5B C4B 1.379(3) . ?
C5B H5B 0.9300 . ?
C4B H4B 0.9300 . ?
C8B C9B 1.502(4) . ?
C8B H8AA 0.9700 . ?
C8B H8BA 0.9700 . ?
C9B H9AA 0.9600 . ?
C9B H9CA 0.9600 . ?
C9B H9BA 0.9600 . ?
O3B C11B 1.368(2) . ?
O3B H7B 0.95(4) . ?
O5B C16B 1.233(3) . ?
O4B C14B 1.369(3) . ?
O4B H10B 0.93(3) . ?
C10B C15B 1.402(3) . ?
C10B C11B 1.408(3) . ?
C10B C16B 1.471(3) . ?
O6B C16B 1.326(3) . ?
O6B H11B 0.92(4) . ?
C11B C12B 1.388(3) . ?
C15B C14B 1.384(3) . ?
C15B H15B 0.9300 . ?
C13B C12B 1.379(3) . ?
C13B C14B 1.398(3) . ?
C13B H13B 0.9300 . ?
C12B H12B 0.9300 . ?
C7A O2A 1.256(3) . ?
C7A N1A 1.327(3) . ?
C7A C1A 1.499(3) . ?
C4A C5A 1.385(3) . ?
C4A C3A 1.385(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.389(3) . ?
C5A H5A 0.9300 . ?
C9A C8A 1.513(3) . ?
C9A H9AB 0.9600 . ?
C9A H9CB 0.9600 . ?
C9A H9BB 0.9600 . ?
O1A C2A 1.368(3) . ?
O1A C8A 1.435(3) . ?
N1A H1A 0.87(3) . ?
N1A H2A 0.89(3) . ?
C1A C6A 1.390(3) . ?
C1A C2A 1.410(3) . ?
C2A C3A 1.390(3) . ?
C8A H8BB 0.9700 . ?
C8A H8AB 0.9700 . ?
C3A H3A 0.9300 . ?
C6A H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14A O4A H10A 111.5(19) . . ?
C11A O3A H7A 105(2) . . ?
C16A O6A H11A 115(3) . . ?
C15A C10A C11A 119.73(19) . . ?
C15A C10A C16A 120.59(19) . . ?
C11A C10A C16A 119.67(19) . . ?
C14A C15A C10A 120.5(2) . . ?
C14A C15A H15A 119.8 . . ?
C10A C15A H15A 119.8 . . ?
C13A C12A C11A 120.2(2) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C12A C13A C14A 120.7(2) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
O4A C14A C15A 119.05(19) . . ?
O4A C14A C13A 121.58(19) . . ?
C15A C14A C13A 119.36(19) . . ?
O5A C16A O6A 123.0(2) . . ?
O5A C16A C10A 121.5(2) . . ?
O6A C16A C10A 115.45(19) . . ?
O3A C11A C12A 118.52(19) . . ?
O3A C11A C10A 121.95(19) . . ?
C12A C11A C10A 119.53(19) . . ?
C2B O1B C8B 118.91(18) . . ?
C6B C1B C2B 118.2(2) . . ?
C6B C1B C7B 116.2(2) . . ?
C2B C1B C7B 125.5(2) . . ?
C7B N1B H1B 121.0(18) . . ?
C7B N1B H2B 121(2) . . ?
H1B N1B H2B 118(3) . . ?
C5B C6B C1B 122.0(2) . . ?
C5B C6B H6B 119.0 . . ?
C1B C6B H6B 119.0 . . ?
O2B C7B N1B 122.0(2) . . ?
O2B C7B C1B 119.0(2) . . ?
N1B C7B C1B 119.0(2) . . ?
O1B C2B C3B 122.0(2) . . ?
O1B C2B C1B 118.32(19) . . ?
C3B C2B C1B 119.7(2) . . ?
C4B C3B C2B 120.6(2) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C4B C5B C6B 119.0(2) . . ?
C4B C5B H5B 120.5 . . ?
C6B C5B H5B 120.5 . . ?
C5B C4B C3B 120.5(2) . . ?
C5B C4B H4B 119.7 . . ?
C3B C4B H4B 119.7 . . ?
O1B C8B C9B 107.2(2) . . ?
O1B C8B H8AA 110.3 . . ?
C9B C8B H8AA 110.3 . . ?
O1B C8B H8BA 110.3 . . ?
C9B C8B H8BA 110.3 . . ?
H8AA C8B H8BA 108.5 . . ?
C8B C9B H9AA 109.5 . . ?
C8B C9B H9CA 109.5 . . ?
H9AA C9B H9CA 109.5 . . ?
C8B C9B H9BA 109.5 . . ?
H9AA C9B H9BA 109.5 . . ?
H9CA C9B H9BA 109.5 . . ?
C11B O3B H7B 104(2) . . ?
C14B O4B H10B 111.0(19) . . ?
C15B C10B C11B 119.45(19) . . ?
C15B C10B C16B 122.10(19) . . ?
C11B C10B C16B 118.44(19) . . ?
C16B O6B H11B 109(2) . . ?
O3B C11B C12B 117.81(19) . . ?
O3B C11B C10B 123.05(19) . . ?
C12B C11B C10B 119.14(19) . . ?
C14B C15B C10B 120.69(19) . . ?
C14B C15B H15B 119.7 . . ?
C10B C15B H15B 119.7 . . ?
O5B C16B O6B 122.4(2) . . ?
O5B C16B C10B 122.18(19) . . ?
O6B C16B C10B 115.45(19) . . ?
C12B C13B C14B 120.3(2) . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B H13B 119.8 . . ?
C13B C12B C11B 121.1(2) . . ?
C13B C12B H12B 119.5 . . ?
C11B C12B H12B 119.5 . . ?
O4B C14B C15B 118.15(19) . . ?
O4B C14B C13B 122.5(2) . . ?
C15B C14B C13B 119.3(2) . . ?
O2A C7A N1A 121.5(2) . . ?
O2A C7A C1A 118.6(2) . . ?
N1A C7A C1A 119.9(2) . . ?
C5A C4A C3A 120.6(2) . . ?
C5A C4A H4A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C4A C5A C6A 119.2(2) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9CB 109.5 . . ?
H9AB C9A H9CB 109.5 . . ?
C8A C9A H9BB 109.5 . . ?
H9AB C9A H9BB 109.5 . . ?
H9CB C9A H9BB 109.5 . . ?
C2A O1A C8A 119.39(17) . . ?
C7A N1A H1A 120(2) . . ?
C7A N1A H2A 118.8(18) . . ?
H1A N1A H2A 120(3) . . ?
C6A C1A C2A 118.3(2) . . ?
C6A C1A C7A 117.06(19) . . ?
C2A C1A C7A 124.6(2) . . ?
O1A C2A C3A 122.1(2) . . ?
O1A C2A C1A 117.78(19) . . ?
C3A C2A C1A 120.2(2) . . ?
O1A C8A C9A 106.44(19) . . ?
O1A C8A H8BB 110.4 . . ?
C9A C8A H8BB 110.4 . . ?
O1A C8A H8AB 110.4 . . ?
C9A C8A H8AB 110.4 . . ?
H8BB C8A H8AB 108.6 . . ?
C4A C3A C2A 120.1(2) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C5A C6A C1A 121.6(2) . . ?
C5A C6A H6A 119.2 . . ?
C1A C6A H6A 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1A 0.87(3) 1.97(3) 2.639(3) 133(3) .
N1B H1B O1B 0.87(3) 2.00(3) 2.670(3) 133(2) .
N1A H2A O5A 0.89(3) 2.06(3) 2.945(3) 167(2) .
N1B H2B O3B 0.89(3) 2.18(3) 3.013(3) 156(3) .
O3A H7A O5A 0.97(3) 1.69(3) 2.568(2) 150(3) .
O3B H7B O5B 0.95(4) 1.69(4) 2.561(3) 151(3) .
O4A H10A O2B 0.95(3) 1.69(3) 2.641(2) 175(3) .
O4B H10B O4A 0.93(3) 1.82(3) 2.748(3) 176(3) 1_455
O6A H11A O2A 0.929(19) 1.59(2) 2.511(2) 171(4) .
O6B H11B O3A 0.92(4) 1.84(4) 2.754(3) 172(4) 1_665

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.067

#===END

data_Form-II
_database_code_depnum_ccdc_archive 'CCDC 719454'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'Form II of 1:1 cocrystal of ethenzamide and gentisic acid'
;
_chemical_name_common            
"'Form II of 1:1 cocrystal of ethenzamide and gentisic acid'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O2, C7 H6 O4'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   7.7217(15)
_cell_length_b                   12.668(3)
_cell_length_c                   15.749(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.44(3)
_cell_angle_gamma                90.00
_cell_volume                     1504.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4270
_cell_measurement_theta_min      2.0827
_cell_measurement_theta_max      31.0024

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area deterctor'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11489
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3708
_reflns_number_gt                3184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Despite repeated crystallization experiments, we always ended up with very
thin plate like crystals for Form II. Of the several data sets collected on
Form II crystals, the structure reported in the manuscript was the best
structure we could ever solve. However, we did try to solve the structure
using TWINSOLVE, but it was not able to find any twin relationships. Therefore
the higher than usual R-factor can be attributed to poor crystal quality
leading to low signal over noise ratio. The fact that the PXRD of the
Form II powder matches with that of the PXRD pattern simulated from the X-ray
structure further confirms the existence of Form II.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1446P)²+7.7900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3708
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.1233
_refine_ls_wR_factor_ref         0.3615
_refine_ls_wR_factor_gt          0.3545
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.7505(5) 0.5198(3) 0.4044(2) 0.0326(8) Uani 1 1 d . . .
O3 O 0.7666(5) 0.5621(3) 0.2464(2) 0.0312(8) Uani 1 1 d . . .
O6 O 0.8752(5) 0.6297(3) 0.5119(2) 0.0348(8) Uani 1 1 d . . .
O4 O 1.1271(5) 0.9259(3) 0.3753(2) 0.0341(8) Uani 1 1 d . . .
C10 C 0.8972(6) 0.6731(3) 0.3697(3) 0.0235(9) Uani 1 1 d . . .
C13 C 0.9917(6) 0.8159(4) 0.2531(3) 0.0276(9) Uani 1 1 d . . .
H13 H 1.0222 0.8640 0.2141 0.033 Uiso 1 1 calc R . .
C14 C 1.0383(6) 0.8360(4) 0.3422(3) 0.0265(9) Uani 1 1 d . . .
C15 C 0.9913(6) 0.7657(4) 0.3994(3) 0.0268(9) Uani 1 1 d . . .
H15 H 1.0222 0.7794 0.4588 0.032 Uiso 1 1 calc R . .
C11 C 0.8542(6) 0.6525(4) 0.2803(3) 0.0259(9) Uani 1 1 d . . .
C16 C 0.8364(6) 0.6005(4) 0.4295(3) 0.0265(9) Uani 1 1 d . . .
C12 C 0.9005(6) 0.7249(4) 0.2222(3) 0.0288(10) Uani 1 1 d . . .
H12 H 0.8700 0.7120 0.1627 0.035 Uiso 1 1 calc R . .
H11 H 0.832(9) 0.567(6) 0.546(5) 0.050(19) Uiso 1 1 d . . .
H10 H 1.173(12) 0.964(8) 0.348(7) 0.09(3) Uiso 1 1 d . . .
H7 H 0.749(9) 0.523(6) 0.294(5) 0.06(2) Uiso 1 1 d . . .
O1 O 0.5016(5) 0.2328(3) 0.6112(2) 0.0317(8) Uani 1 1 d . . .
O2 O 0.7635(6) 0.5184(3) 0.6224(2) 0.0415(10) Uani 1 1 d . . .
N1 N 0.6182(6) 0.3938(3) 0.5342(3) 0.0287(9) Uani 1 1 d . . .
C7 C 0.6823(6) 0.4323(4) 0.6130(3) 0.0259(9) Uani 1 1 d . . .
C2 C 0.5766(6) 0.2751(4) 0.6908(3) 0.0275(10) Uani 1 1 d . . .
C6 C 0.7363(7) 0.4185(4) 0.7716(3) 0.0292(10) Uani 1 1 d . . .
H6 H 0.7908 0.4841 0.7729 0.035 Uiso 1 1 calc R . .
C1 C 0.6601(6) 0.3734(4) 0.6913(3) 0.0258(9) Uani 1 1 d . . .
C8 C 0.4238(7) 0.1293(4) 0.6063(4) 0.0332(11) Uani 1 1 d . . .
H8A H 0.3294 0.1267 0.6381 0.040 Uiso 1 1 calc R . .
H8B H 0.5124 0.0767 0.6302 0.040 Uiso 1 1 calc R . .
C5 C 0.7331(7) 0.3685(4) 0.8495(3) 0.0357(11) Uani 1 1 d . . .
H5 H 0.7855 0.3994 0.9023 0.043 Uiso 1 1 calc R . .
C4 C 0.6498(8) 0.2709(4) 0.8467(3) 0.0379(12) Uani 1 1 d . . .
H4 H 0.6468 0.2367 0.8986 0.045 Uiso 1 1 calc R . .
C3 C 0.5713(7) 0.2233(4) 0.7691(3) 0.0342(11) Uani 1 1 d . . .
H3 H 0.5159 0.1581 0.7687 0.041 Uiso 1 1 calc R . .
C9 C 0.3511(8) 0.1101(4) 0.5097(4) 0.0397(12) Uani 1 1 d . . .
H9A H 0.2658 0.1637 0.4871 0.060 Uiso 1 1 calc R . .
H9B H 0.2952 0.0421 0.5017 0.060 Uiso 1 1 calc R . .
H9C H 0.4465 0.1124 0.4795 0.060 Uiso 1 1 calc R . .
H2 H 0.647(8) 0.421(5) 0.495(4) 0.034(16) Uiso 1 1 d . . .
H1 H 0.556(8) 0.321(5) 0.530(4) 0.040(17) 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 C16 1.236(6) . ?
O3 C11 1.377(6) . ?
O3 H7 0.93(8) . ?
O6 C16 1.321(6) . ?
O6 H11 1.05(8) . ?
O4 C14 1.373(6) . ?
O4 H10 0.79(11) . ?
C10 C11 1.401(6) . ?
C10 C15 1.405(6) . ?
C10 C16 1.463(6) . ?
C13 C12 1.384(7) . ?
C13 C14 1.395(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(6) . ?
C15 H15 0.9300 . ?
C11 C12 1.395(6) . ?
C12 H12 0.9300 . ?
O1 C2 1.371(6) . ?
O1 C8 1.438(6) . ?
O2 C7 1.251(6) . ?
N1 C7 1.326(6) . ?
N1 H2 0.78(7) . ?
N1 H1 1.03(7) . ?
C7 C1 1.482(6) . ?
C2 C1 1.403(7) . ?
C2 C3 1.405(7) . ?
C6 C5 1.385(7) . ?
C6 C1 1.398(7) . ?
C6 H6 0.9300 . ?
C8 C9 1.524(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C5 C4 1.389(8) . ?
C5 H5 0.9300 . ?
C4 C3 1.380(8) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C11 O3 H7 106(5) . . ?
C16 O6 H11 105(4) . . ?
C14 O4 H10 124(8) . . ?
C11 C10 C15 118.9(4) . . ?
C11 C10 C16 119.3(4) . . ?
C15 C10 C16 121.7(4) . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 O4 118.1(4) . . ?
C15 C14 C13 119.7(4) . . ?
O4 C14 C13 122.2(4) . . ?
C14 C15 C10 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O3 C11 C12 117.8(4) . . ?
O3 C11 C10 122.3(4) . . ?
C12 C11 C10 119.8(4) . . ?
O5 C16 O6 122.6(4) . . ?
O5 C16 C10 122.6(4) . . ?
O6 C16 C10 114.8(4) . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C2 O1 C8 119.6(4) . . ?
C7 N1 H2 118(5) . . ?
C7 N1 H1 117(4) . . ?
H2 N1 H1 123(6) . . ?
O2 C7 N1 120.5(4) . . ?
O2 C7 C1 119.1(4) . . ?
N1 C7 C1 120.4(4) . . ?
O1 C2 C1 117.0(4) . . ?
O1 C2 C3 122.3(5) . . ?
C1 C2 C3 120.7(5) . . ?
C5 C6 C1 122.0(5) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C6 C1 C2 118.1(4) . . ?
C6 C1 C7 116.5(4) . . ?
C2 C1 C7 125.4(4) . . ?
O1 C8 C9 105.0(4) . . ?
O1 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
O1 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C6 C5 C4 118.4(5) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C3 C4 C5 121.9(5) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 1.03(7) 1.81(7) 2.629(5) 133(5) .
N1 H2 O5 0.78(7) 2.17(7) 2.944(5) 168(6) .
O3 H7 O5 0.93(8) 1.74(8) 2.575(5) 148(7) .
O6 H11 O2 1.05(8) 1.54(7) 2.531(5) 154(6) .
O4 H10 O3 0.79(11) 2.06(11) 2.828(5) 165(10) 2_755

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.125

#===END

data_Form-III
_database_code_depnum_ccdc_archive 'CCDC 719455'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
'Form III of 1:1 cocrystal of ethenzamide and gentisic acid'
;
_chemical_name_common            
"'Form III of 1:1 cocrystal of ethenzamide and gentisic acid'"
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 N O2, C7 H6 O4'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   7.1283(14)
_cell_length_b                   16.242(3)
_cell_length_c                   12.904(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.25(3)
_cell_angle_gamma                90.00
_cell_volume                     1485.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3510
_cell_measurement_theta_min      2.0229
_cell_measurement_theta_max      31.0775

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area deterctor'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11896
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3667
_reflns_number_gt                3207
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.3976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.04145(18) 0.70347(7) 0.66365(9) 0.0288(3) Uani 1 1 d . . .
O1 O 0.15736(17) 0.95221(7) 0.72081(9) 0.0269(3) Uani 1 1 d . . .
O5 O 0.05343(18) 0.73071(7) 0.40589(9) 0.0293(3) Uani 1 1 d . . .
O6 O 0.08825(18) 0.61483(7) 0.49966(9) 0.0272(3) Uani 1 1 d . . .
C1 C 0.0819(2) 0.81826(10) 0.78020(12) 0.0229(3) Uani 1 1 d . . .
O3 O 0.0902(2) 0.72895(7) 0.20872(10) 0.0353(3) Uani 1 1 d . . .
O4 O 0.20493(19) 0.39285(7) 0.23786(10) 0.0317(3) Uani 1 1 d . . .
C10 C 0.1077(2) 0.60630(9) 0.31757(12) 0.0224(3) Uani 1 1 d . . .
C15 C 0.1352(2) 0.52060(10) 0.32429(13) 0.0236(3) Uani 1 1 d . . .
H15 H 0.1318 0.4939 0.3878 0.028 Uiso 1 1 calc R . .
C13 C 0.1728(2) 0.51656(10) 0.14166(13) 0.0278(4) Uani 1 1 d . . .
H13 H 0.1945 0.4865 0.0828 0.033 Uiso 1 1 calc R . .
C2 C 0.1223(2) 0.90210(10) 0.80186(12) 0.0227(3) Uani 1 1 d . . .
C16 C 0.0796(2) 0.65559(10) 0.41071(12) 0.0234(3) Uani 1 1 d . . .
N1 N 0.1141(3) 0.82468(9) 0.59439(12) 0.0334(4) Uani 1 1 d . . .
C7 C 0.0775(2) 0.77909(10) 0.67496(13) 0.0243(3) Uani 1 1 d . . .
C11 C 0.1128(2) 0.64659(10) 0.22133(13) 0.0264(4) Uani 1 1 d . . .
C12 C 0.1463(3) 0.60054(11) 0.13386(13) 0.0294(4) Uani 1 1 d . . .
H12 H 0.1509 0.6266 0.0700 0.035 Uiso 1 1 calc R . .
C5 C 0.0411(3) 0.79769(11) 0.96320(13) 0.0288(4) Uani 1 1 d . . .
H5 H 0.0113 0.7633 1.0166 0.035 Uiso 1 1 calc R . .
C8 C 0.1635(2) 1.03997(10) 0.73644(14) 0.0272(4) Uani 1 1 d . . .
H8A H 0.2734 1.0550 0.7836 0.033 Uiso 1 1 calc R . .
H8B H 0.0513 1.0585 0.7660 0.033 Uiso 1 1 calc R . .
C6 C 0.0404(2) 0.76788(10) 0.86241(13) 0.0261(4) Uani 1 1 d . . .
H6 H 0.0114 0.7128 0.8492 0.031 Uiso 1 1 calc R . .
C3 C 0.1275(2) 0.93162(10) 0.90363(13) 0.0267(4) Uani 1 1 d . . .
H3 H 0.1583 0.9864 0.9182 0.032 Uiso 1 1 calc R . .
C14 C 0.1673(2) 0.47592(10) 0.23663(13) 0.0244(3) Uani 1 1 d . . .
C9 C 0.1734(3) 1.07839(11) 0.63127(15) 0.0345(4) Uani 1 1 d . . .
H9A H 0.2860 1.0602 0.6035 0.052 Uiso 1 1 calc R . .
H9B H 0.1757 1.1372 0.6380 0.052 Uiso 1 1 calc R . .
H9C H 0.0650 1.0622 0.5851 0.052 Uiso 1 1 calc R . .
C4 C 0.0868(2) 0.87936(11) 0.98307(13) 0.0278(4) Uani 1 1 d . . .
H4 H 0.0903 0.8995 1.0507 0.033 Uiso 1 1 calc R . .
H2 H 0.100(3) 0.8014(14) 0.532(2) 0.047(7) Uiso 1 1 d . . .
H1 H 0.144(3) 0.8807(13) 0.6033(16) 0.035(6) Uiso 1 1 d . . .
H11 H 0.072(4) 0.6545(17) 0.556(2) 0.068(8) Uiso 1 1 d . . .
H10 H 0.134(4) 0.3671(18) 0.278(2) 0.070(9) Uiso 1 1 d . . .
H7 H 0.079(5) 0.751(2) 0.277(3) 0.090(11) 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
O2 C7 1.260(2) . ?
O1 C2 1.3696(19) . ?
O1 C8 1.4395(19) . ?
O5 C16 1.2347(19) . ?
O6 C16 1.3207(19) . ?
O6 H11 0.98(3) . ?
C1 C6 1.397(2) . ?
C1 C2 1.413(2) . ?
C1 C7 1.497(2) . ?
O3 C11 1.355(2) . ?
O3 H7 0.96(3) . ?
O4 C14 1.3754(19) . ?
O4 H10 0.87(3) . ?
C10 C15 1.407(2) . ?
C10 C11 1.408(2) . ?
C10 C16 1.476(2) . ?
C15 C14 1.384(2) . ?
C15 H15 0.9300 . ?
C13 C12 1.379(2) . ?
C13 C14 1.396(2) . ?
C13 H13 0.9300 . ?
C2 C3 1.395(2) . ?
N1 C7 1.325(2) . ?
N1 H2 0.88(3) . ?
N1 H1 0.94(2) . ?
C11 C12 1.396(2) . ?
C12 H12 0.9300 . ?
C5 C4 1.383(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C8 C9 1.502(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6 0.9300 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C8 119.12(13) . . ?
C16 O6 H11 108.1(16) . . ?
C6 C1 C2 118.02(14) . . ?
C6 C1 C7 117.04(14) . . ?
C2 C1 C7 124.93(15) . . ?
C11 O3 H7 105.7(19) . . ?
C14 O4 H10 110.7(19) . . ?
C15 C10 C11 119.82(14) . . ?
C15 C10 C16 121.12(14) . . ?
C11 C10 C16 119.02(14) . . ?
C14 C15 C10 120.18(14) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C12 C13 C14 120.99(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
O1 C2 C3 121.76(14) . . ?
O1 C2 C1 118.15(14) . . ?
C3 C2 C1 120.09(15) . . ?
O5 C16 O6 122.12(15) . . ?
O5 C16 C10 121.88(14) . . ?
O6 C16 C10 115.99(14) . . ?
C7 N1 H2 117.4(16) . . ?
C7 N1 H1 120.5(13) . . ?
H2 N1 H1 122(2) . . ?
O2 C7 N1 120.59(15) . . ?
O2 C7 C1 120.22(14) . . ?
N1 C7 C1 119.19(15) . . ?
O3 C11 C12 117.41(15) . . ?
O3 C11 C10 123.42(14) . . ?
C12 C11 C10 119.17(15) . . ?
C13 C12 C11 120.32(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C4 C5 C6 119.03(16) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
O1 C8 C9 106.76(14) . . ?
O1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C5 C6 C1 121.87(16) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C4 C3 C2 119.98(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O4 C14 C15 123.67(15) . . ?
O4 C14 C13 116.73(14) . . ?
C15 C14 C13 119.51(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C4 C3 120.96(16) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.94(2) 1.90(2) 2.6338(19) 132.8(17) .
N1 H2 O5 0.88(3) 2.00(3) 2.864(2) 169(2) .
O3 H7 O5 0.96(3) 1.73(3) 2.5863(19) 148(3) .
O4 H10 O2 0.87(3) 1.91(3) 2.7628(19) 166(3) 3_566
O6 H11 O2 0.98(3) 1.64(3) 2.6109(17) 168(3) .
C5 H5 O3 0.93 2.54 3.342(2) 144.1 1_556
C6 H6 O4 0.93 2.49 3.325(2) 149.3 3_566
C8 H8B O4 0.97 2.58 3.448(2) 148.9 4_576

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.060

#===END


