# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'William Jones'
_publ_contact_author_email       WJ10@CAM.AC.UK

_publ_section_title              
;
Control and interconversion of cocrystal stoichiometry
in grinding: stepwise mechanism for the formation of a hydrogen-bonded
cocrystal
;
loop_
_publ_author_name
'William Jones'
'Tomislav Friscic'
'Shyam Karki'

# Attachment 'deposit_revised.cif'

data_(na)2.(mal)
_database_code_depnum_ccdc_archive 'CCDC 695329'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:malonic acid 2/1
;
_chemical_name_common            'nicotinamide:malonic acid 2/1'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H6 N2 O), C3 H4 O4'
_chemical_formula_sum            'C15 H16 N4 O6'
_chemical_formula_weight         348.32
_chemical_absolute_configuration 
;
1473 Friedel pairs were averaged for the refinement.
;

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   32.9054(6)
_cell_length_b                   4.0078(1)
_cell_length_c                   12.3689(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1631.19(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    11834
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions were
refined satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            8534
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         27.86
_reflns_number_total             1983
_reflns_number_gt                1780
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0487P)²+0.2847P] 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         1983
_refine_ls_number_parameters     232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.07251(5) 0.1344(5) 0.41728(13) 0.0423(4) Uani 1 1 d . . .
O2 O 0.32014(5) -0.0976(4) -0.10065(13) 0.0406(4) Uani 1 1 d . . .
O3 O 0.31892(5) 0.2583(5) 0.42063(14) 0.0358(4) Uani 1 1 d . . .
H3A H 0.2996(9) 0.120(7) 0.477(2) 0.043 Uiso 1 1 d . . .
O4 O 0.35649(6) 0.3646(5) 0.56534(14) 0.0480(5) Uani 1 1 d . . .
O5 O 0.39507(6) 0.2974(5) 0.23603(14) 0.0465(4) Uani 1 1 d . . .
O6 O 0.43553(5) 0.2770(4) 0.37990(13) 0.0348(4) Uani 1 1 d . . .
H6A H 0.4519(9) 0.134(7) 0.332(2) 0.042 Uiso 1 1 d . . .
N1 N -0.01705(6) -0.4073(5) 0.26547(15) 0.0338(4) Uani 1 1 d . . .
N2 N 0.11471(6) 0.0964(6) 0.27426(17) 0.0437(5) Uani 1 1 d . . .
H2A H 0.1350 0.1893 0.3096 0.052 Uiso 1 1 calc R . .
H2B H 0.1180 0.0332 0.2067 0.052 Uiso 1 1 calc R . .
N3 N 0.22956(6) 0.4424(5) 0.04466(14) 0.0318(4) Uani 1 1 d . . .
N4 N 0.36360(6) -0.0186(6) 0.03800(16) 0.0455(5) Uani 1 1 d . . .
H4A H 0.3838 -0.1169 0.0040 0.055 Uiso 1 1 calc R . .
H4B H 0.3673 0.0618 0.1035 0.055 Uiso 1 1 calc R . .
C1 C 0.04583(7) -0.1052(5) 0.25842(17) 0.0289(4) Uani 1 1 d . . .
C2 C 0.04215(7) -0.0832(6) 0.14630(18) 0.0339(5) Uani 1 1 d . . .
H2 H 0.0629 0.0211 0.1048 0.041 Uiso 1 1 calc R . .
C3 C 0.00824(7) -0.2141(6) 0.0960(2) 0.0370(5) Uani 1 1 d . . .
H3 H 0.0049 -0.1939 0.0200 0.044 Uiso 1 1 calc R . .
C4 C -0.02076(7) -0.3746(6) 0.15781(19) 0.0348(5) Uani 1 1 d . . .
H4 H -0.0440 -0.4648 0.1231 0.042 Uiso 1 1 calc R . .
C5 C 0.01518(7) -0.2713(5) 0.31405(18) 0.0294(5) Uani 1 1 d . . .
H5 H 0.0173 -0.2890 0.3904 0.035 Uiso 1 1 calc R . .
C6 C 0.07921(7) 0.0517(6) 0.32279(18) 0.0321(5) Uani 1 1 d . . .
C7 C 0.29401(6) 0.1704(5) 0.05483(16) 0.0273(4) Uani 1 1 d . . .
C8 C 0.29212(7) 0.1802(6) 0.16672(18) 0.0351(5) Uani 1 1 d . . .
H8 H 0.3140 0.0967 0.2091 0.042 Uiso 1 1 calc R . .
C9 C 0.25781(7) 0.3139(6) 0.21610(19) 0.0363(5) Uani 1 1 d . . .
H9 H 0.2556 0.3159 0.2927 0.044 Uiso 1 1 calc R . .
C10 C 0.22724(7) 0.4430(6) 0.15315(19) 0.0342(5) Uani 1 1 d . . .
H10 H 0.2039 0.5348 0.1871 0.041 Uiso 1 1 calc R . .
C11 C 0.26194(7) 0.3070(6) -0.00276(18) 0.0299(5) Uani 1 1 d . . .
H11 H 0.2631 0.3038 -0.0795 0.036 Uiso 1 1 calc R . .
C12 C 0.32768(7) 0.0082(6) -0.00941(17) 0.0312(5) Uani 1 1 d . . .
C13 C 0.34946(6) 0.3984(5) 0.46960(18) 0.0285(4) Uani 1 1 d . . .
C14 C 0.37621(8) 0.6026(5) 0.3957(2) 0.0343(5) Uani 1 1 d . . .
H14A H 0.3934 0.7541 0.4394 0.041 Uiso 1 1 calc R . .
H14B H 0.3590 0.7409 0.3476 0.041 Uiso 1 1 calc R . .
C15 C 0.40311(6) 0.3783(5) 0.32776(17) 0.0292(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.235(3) . ?
O2 C12 1.231(3) . ?
O3 C13 1.301(3) . ?
O3 H3A 1.10(3) . ?
O4 C13 1.214(3) . ?
O5 C15 1.209(3) . ?
O6 C15 1.311(3) . ?
O6 H6A 0.99(3) . ?
N1 C5 1.335(3) . ?
N1 C4 1.344(3) . ?
N2 C6 1.326(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C11 1.332(3) . ?
N3 C10 1.344(3) . ?
N4 C12 1.324(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C5 1.391(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.495(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C11 1.386(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.510(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.510(3) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C13 O3 H3A 111.6(15) . . ?
C15 O6 H6A 109.1(17) . . ?
C5 N1 C4 118.6(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 N3 C10 119.1(2) . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 C1 C2 117.3(2) . . ?
C5 C1 C6 118.07(19) . . ?
C2 C1 C6 124.5(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
N1 C4 C3 122.1(2) . . ?
N1 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
N1 C5 C1 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C1 C5 H5 118.4 . . ?
O1 C6 N2 123.3(2) . . ?
O1 C6 C1 119.1(2) . . ?
N2 C6 C1 117.6(2) . . ?
C11 C7 C8 117.9(2) . . ?
C11 C7 C12 117.27(19) . . ?
C8 C7 C12 124.8(2) . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N3 C10 C9 121.6(2) . . ?
N3 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N3 C11 C7 122.9(2) . . ?
N3 C11 H11 118.5 . . ?
C7 C11 H11 118.5 . . ?
O2 C12 N4 123.9(2) . . ?
O2 C12 C7 118.9(2) . . ?
N4 C12 C7 117.19(19) . . ?
O4 C13 O3 123.6(2) . . ?
O4 C13 C14 122.7(2) . . ?
O3 C13 C14 113.7(2) . . ?
C13 C14 C15 110.78(16) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O5 C15 O6 123.8(2) . . ?
O5 C15 C14 123.4(2) . . ?
O6 C15 C14 112.74(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 2.2(3) . . . . ?
C6 C1 C2 C3 -174.6(2) . . . . ?
C1 C2 C3 C4 -2.2(4) . . . . ?
C5 N1 C4 C3 1.9(3) . . . . ?
C2 C3 C4 N1 0.1(4) . . . . ?
C4 N1 C5 C1 -1.9(3) . . . . ?
C2 C1 C5 N1 -0.2(3) . . . . ?
C6 C1 C5 N1 176.8(2) . . . . ?
C5 C1 C6 O1 -25.2(3) . . . . ?
C2 C1 C6 O1 151.6(2) . . . . ?
C5 C1 C6 N2 155.2(2) . . . . ?
C2 C1 C6 N2 -28.0(3) . . . . ?
C11 C7 C8 C9 2.4(4) . . . . ?
C12 C7 C8 C9 -174.9(2) . . . . ?
C7 C8 C9 C10 -2.1(4) . . . . ?
C11 N3 C10 C9 1.4(4) . . . . ?
C8 C9 C10 N3 0.2(4) . . . . ?
C10 N3 C11 C7 -1.2(3) . . . . ?
C8 C7 C11 N3 -0.7(3) . . . . ?
C12 C7 C11 N3 176.7(2) . . . . ?
C11 C7 C12 O2 -24.3(3) . . . . ?
C8 C7 C12 O2 153.0(2) . . . . ?
C11 C7 C12 N4 157.5(2) . . . . ?
C8 C7 C12 N4 -25.3(4) . . . . ?
O4 C13 C14 C15 102.6(3) . . . . ?
O3 C13 C14 C15 -76.1(3) . . . . ?
C13 C14 C15 O5 97.4(3) . . . . ?
C13 C14 C15 O6 -81.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037

data_(na).(fum)
_database_code_depnum_ccdc_archive 'CCDC 695330'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nictinamide:fumaric acid 1:1
;
_chemical_name_common            'nictinamide:fumaric acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C4 H4 O4'
_chemical_formula_sum            'C10 H10 N2 O5'
_chemical_formula_weight         238.20

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   5.53140(10)
_cell_length_b                   13.7844(4)
_cell_length_c                   14.2056(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5900(10)
_cell_angle_gamma                90.00
_cell_volume                     1082.03(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    10762
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      34.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions were
refined satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            16034
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         35.03
_reflns_number_total             4712
_reflns_number_gt                2963
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0638P)²+0.1671P] 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         4712
_refine_ls_number_parameters     160
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.81471(15) 0.35939(6) 0.80960(7) 0.0312(2) Uani 1 1 d . . .
O2 O 1.32228(15) 0.39918(7) 0.95064(7) 0.0361(2) Uani 1 1 d . . .
O3 O 1.16741(15) 0.26024(7) 0.89169(7) 0.0347(2) Uani 1 1 d D . .
H3A H 1.043(3) 0.3008(12) 0.8606(11) 0.042 Uiso 1 1 d D . .
O4 O 2.06945(15) 0.27379(7) 1.12756(7) 0.0334(2) Uani 1 1 d . . .
O5 O 1.88068(15) 0.13897(7) 1.07628(7) 0.0325(2) Uani 1 1 d D . .
H5A H 2.020(2) 0.1021(12) 1.1075(11) 0.039 Uiso 1 1 d D . .
N1 N 0.21648(17) 0.46402(8) 0.65968(7) 0.0280(2) Uani 1 1 d . . .
N2 N 0.92361(18) 0.50653(8) 0.86583(8) 0.0318(2) Uani 1 1 d . . .
H2A H 1.0501 0.4826 0.8977 0.038 Uiso 1 1 calc R . .
H2B H 0.8930 0.5691 0.8679 0.038 Uiso 1 1 calc R . .
C1 C 0.40842(19) 0.43090(8) 0.71104(8) 0.0255(2) Uani 1 1 d . . .
H1 H 0.4362 0.3629 0.7140 0.031 Uiso 1 1 calc R . .
C2 C 0.56854(18) 0.49256(8) 0.76024(8) 0.0226(2) Uani 1 1 d . . .
C3 C 0.5255(2) 0.59159(9) 0.75584(9) 0.0286(2) Uani 1 1 d . . .
H3 H 0.6317 0.6356 0.7885 0.034 Uiso 1 1 calc R . .
C4 C 0.3254(2) 0.62591(9) 0.70323(10) 0.0312(3) Uani 1 1 d . . .
H4 H 0.2920 0.6934 0.6997 0.037 Uiso 1 1 calc R . .
C5 C 0.1762(2) 0.55977(9) 0.65625(9) 0.0291(2) Uani 1 1 d . . .
H5 H 0.0397 0.5831 0.6201 0.035 Uiso 1 1 calc R . .
C6 C 0.77935(18) 0.44829(8) 0.81478(8) 0.0234(2) Uani 1 1 d . . .
C7 C 1.32592(18) 0.31144(9) 0.94354(8) 0.0258(2) Uani 1 1 d . . .
C8 C 1.51196(18) 0.24939(9) 0.99268(9) 0.0265(2) Uani 1 1 d . . .
H8 H 1.4947 0.1808 0.9918 0.032 Uiso 1 1 calc R . .
C9 C 1.70150(19) 0.28954(9) 1.03758(9) 0.0277(2) Uani 1 1 d . . .
H9 H 1.7111 0.3583 1.0394 0.033 Uiso 1 1 calc R . .
C10 C 1.90041(18) 0.23274(9) 1.08530(8) 0.0254(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2436(14) . ?
O2 C7 1.2139(15) . ?
O3 C7 1.3233(14) . ?
O3 H3A 0.976(13) . ?
O4 C10 1.2264(13) . ?
O5 C10 1.3031(15) . ?
O5 H5A 1.009(13) . ?
N1 C5 1.3389(16) . ?
N1 C1 1.3409(13) . ?
N2 C6 1.3247(14) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.3926(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.3867(16) . ?
C2 C6 1.5002(14) . ?
C3 C4 1.3900(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3813(16) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.4875(15) . ?
C8 C9 1.3236(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4886(15) . ?
C9 H9 0.9500 . ?

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
C7 O3 H3A 112.5(11) . . ?
C10 O5 H5A 113.4(10) . . ?
C5 N1 C1 118.80(10) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.36(10) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.31(9) . . ?
C3 C2 C6 123.47(9) . . ?
C1 C2 C6 118.22(10) . . ?
C2 C3 C4 119.35(10) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.62(11) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.56(10) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
O1 C6 N2 122.48(9) . . ?
O1 C6 C2 119.40(9) . . ?
N2 C6 C2 118.11(10) . . ?
O2 C7 O3 124.37(10) . . ?
O2 C7 C8 123.21(10) . . ?
O3 C7 C8 112.43(10) . . ?
C9 C8 C7 120.12(11) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 123.55(11) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
O4 C10 O5 124.36(10) . . ?
O4 C10 C9 120.78(11) . . ?
O5 C10 C9 114.84(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.59(18) . . . . ?
N1 C1 C2 C3 0.33(18) . . . . ?
N1 C1 C2 C6 -179.33(11) . . . . ?
C1 C2 C3 C4 0.21(19) . . . . ?
C6 C2 C3 C4 179.85(12) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C1 N1 C5 C4 0.3(2) . . . . ?
C3 C4 C5 N1 0.2(2) . . . . ?
C3 C2 C6 O1 -174.84(12) . . . . ?
C1 C2 C6 O1 4.80(17) . . . . ?
C3 C2 C6 N2 4.12(18) . . . . ?
C1 C2 C6 N2 -176.23(11) . . . . ?
O2 C7 C8 C9 -8.6(2) . . . . ?
O3 C7 C8 C9 171.27(12) . . . . ?
C7 C8 C9 C10 -177.55(11) . . . . ?
C8 C9 C10 O4 -178.49(13) . . . . ?
C8 C9 C10 O5 2.93(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        35.03
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053

data_(na).(glu)
_database_code_depnum_ccdc_archive 'CCDC 695331'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:glutaric acid 1:1
;
_chemical_name_common            'nicotinamide:glutaric acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C5 H8 O4'
_chemical_formula_sum            'C11 H14 N2 O5'
_chemical_formula_weight         254.24

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.4556(5)
_cell_length_b                   7.3692(6)
_cell_length_c                   15.1945(13)
_cell_angle_alpha                99.413(5)
_cell_angle_beta                 94.592(5)
_cell_angle_gamma                104.775(3)
_cell_volume                     577.95(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    10439
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions were
refined satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            4270
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         24.93
_reflns_number_total             1964
_reflns_number_gt                1467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0504P)²+0.2989P] 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         1964
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
O2 O 1.2613(3) -0.0662(2) 0.35623(11) 0.0367(5) Uani 1 1 d . . .
O3 O 0.8604(3) -0.2499(3) 0.32587(12) 0.0359(5) Uani 1 1 d . . .
H3A H 0.874(6) -0.261(4) 0.386(2) 0.043 Uiso 1 1 d . . .
O4 O 0.3437(3) -0.3282(3) 0.01925(12) 0.0381(5) Uani 1 1 d . . .
O5 O 0.5639(4) -0.1904(3) -0.08175(12) 0.0388(5) Uani 1 1 d . . .
H5A H 0.423(6) -0.234(4) -0.116(2) 0.047 Uiso 1 1 d . . .
C7 C 1.0683(5) -0.1435(3) 0.30295(15) 0.0268(6) Uani 1 1 d . . .
C8 C 1.0512(4) -0.1251(3) 0.20648(15) 0.0268(6) Uani 1 1 d . . .
H8A H 1.1703 -0.1895 0.1772 0.032 Uiso 1 1 calc R . .
H8B H 1.1111 0.0122 0.2037 0.032 Uiso 1 1 calc R . .
C9 C 0.7863(4) -0.2071(3) 0.15184(15) 0.0271(6) Uani 1 1 d . . .
H9A H 0.7284 -0.3466 0.1498 0.032 Uiso 1 1 calc R . .
H9B H 0.6626 -0.1478 0.1813 0.032 Uiso 1 1 calc R . .
C10 C 0.7938(5) -0.1689(4) 0.05715(15) 0.0294(6) Uani 1 1 d . . .
H10A H 0.8586 -0.0294 0.0604 0.035 Uiso 1 1 calc R . .
H10B H 0.9169 -0.2300 0.0285 0.035 Uiso 1 1 calc R . .
C11 C 0.5412(5) -0.2397(3) -0.00161(15) 0.0276(6) Uani 1 1 d . . .
O1 O 1.1481(3) -0.6780(3) 0.51342(11) 0.0383(5) Uani 1 1 d . . .
N1 N 0.8477(4) -0.6943(3) 0.20825(13) 0.0312(5) Uani 1 1 d . . .
C1 C 0.8140(5) -0.7393(3) 0.28926(16) 0.0305(6) Uani 1 1 d . . .
H1 H 0.6498 -0.8121 0.2976 0.037 Uiso 1 1 calc R . .
N2 N 0.7463(4) -0.8466(3) 0.46206(15) 0.0482(7) Uani 1 1 d . . .
H2A H 0.7211 -0.8792 0.5145 0.058 Uiso 1 1 calc R . .
H2B H 0.6223 -0.8870 0.4168 0.058 Uiso 1 1 calc R . .
C2 C 1.0066(5) -0.6850(3) 0.36154(15) 0.0266(6) Uani 1 1 d . . .
C3 C 1.2456(5) -0.5775(3) 0.34849(16) 0.0315(6) Uani 1 1 d . . .
H3 H 1.3818 -0.5358 0.3965 0.038 Uiso 1 1 calc R . .
C4 C 1.2834(5) -0.5318(4) 0.26546(17) 0.0331(6) Uani 1 1 d . . .
H4 H 1.4460 -0.4599 0.2551 0.040 Uiso 1 1 calc R . .
C5 C 1.0790(5) -0.5931(4) 0.19714(16) 0.0312(6) Uani 1 1 d . . .
H5 H 1.1055 -0.5613 0.1399 0.037 Uiso 1 1 calc R . .
C6 C 0.9688(5) -0.7377(3) 0.45133(16) 0.0297(6) Uani 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 1.223(3) . ?
O3 C7 1.312(3) . ?
O3 H3A 0.93(3) . ?
O4 C11 1.205(3) . ?
O5 C11 1.333(3) . ?
O5 H5A 0.85(3) . ?
C7 C8 1.492(3) . ?
C8 C9 1.530(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.512(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.501(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O1 C6 1.240(3) . ?
N1 C5 1.331(3) . ?
N1 C1 1.341(3) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
N2 C6 1.313(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C2 C3 1.390(3) . ?
C2 C6 1.494(3) . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?

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
C7 O3 H3A 113.8(18) . . ?
C11 O5 H5A 111(2) . . ?
O2 C7 O3 122.8(2) . . ?
O2 C7 C8 122.6(2) . . ?
O3 C7 C8 114.67(19) . . ?
C7 C8 C9 116.1(2) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 110.42(19) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 114.7(2) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O4 C11 O5 123.8(2) . . ?
O4 C11 C10 125.9(2) . . ?
O5 C11 C10 110.3(2) . . ?
C5 N1 C1 117.8(2) . . ?
N1 C1 C2 123.4(2) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 C6 123.2(2) . . ?
C3 C2 C6 119.1(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 121.9(2) . . ?
O1 C6 C2 119.2(2) . . ?
N2 C6 C2 118.9(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 -171.9(2) . . . . ?
O3 C7 C8 C9 8.5(3) . . . . ?
C7 C8 C9 C10 176.8(2) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C11 O4 -3.3(4) . . . . ?
C9 C10 C11 O5 176.6(2) . . . . ?
C5 N1 C1 C2 0.3(4) . . . . ?
N1 C1 C2 C3 0.4(4) . . . . ?
N1 C1 C2 C6 -179.2(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C6 C2 C3 C4 178.6(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
C1 C2 C6 O1 -177.5(2) . . . . ?
C3 C2 C6 O1 2.9(4) . . . . ?
C1 C2 C6 N2 2.7(4) . . . . ?
C3 C2 C6 N2 -176.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        24.93
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.059

data_(na).(adi)
_database_code_depnum_ccdc_archive 'CCDC 695332'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:adipic acid 1:1
;
_chemical_name_common            'nicotinamide:adipic acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 O4, C6 H6 N2 O'
_chemical_formula_sum            'C12 H16 N2 O5'
_chemical_formula_weight         268.27

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0110(1)
_cell_length_b                   5.3379(1)
_cell_length_c                   24.0348(6)
_cell_angle_alpha                93.036(1)
_cell_angle_beta                 92.753(1)
_cell_angle_gamma                92.189(1)
_cell_volume                     640.71(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    11039
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions
were refined satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            8840
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         29.10
_reflns_number_total             3376
_reflns_number_gt                2703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0523P)²+0.1834P] 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         3376
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O -0.12964(17) 0.57741(17) 0.30422(4) 0.0342(2) Uani 1 1 d . . .
O2 O 0.5906(2) 0.08361(17) 0.08203(4) 0.0347(2) Uani 1 1 d . . .
H2A H 0.711(3) 0.089(3) 0.1129(8) 0.042 Uiso 1 1 d . . .
O3 O 0.4588(2) 0.44511(18) 0.12069(4) 0.0386(3) Uani 1 1 d . . .
O4 O -0.2209(2) -0.0087(2) 0.36201(5) 0.0451(3) Uani 1 1 d . . .
H4A H -0.162(4) -0.145(4) 0.3442(8) 0.054 Uiso 1 1 d . . .
O5 O 0.1630(2) -0.03268(19) 0.41150(4) 0.0415(3) Uani 1 1 d . . .
N1 N -0.0475(2) 0.0816(2) 0.16829(5) 0.0302(2) Uani 1 1 d . . .
N2 N 0.3036(2) 0.5545(2) 0.33207(5) 0.0312(3) Uani 1 1 d . . .
H2N1 H 0.2906 0.6744 0.3582 0.037 Uiso 1 1 calc R . .
H2N2 H 0.4573 0.4833 0.3277 0.037 Uiso 1 1 calc R . .
C1 C 0.1229(2) 0.2779(2) 0.25538(5) 0.0249(2) Uani 1 1 d . . .
C2 C 0.3216(2) 0.1036(2) 0.25886(5) 0.0286(3) Uani 1 1 d . . .
H2 H 0.4480 0.1111 0.2897 0.034 Uiso 1 1 calc R . .
C3 C 0.3313(3) -0.0813(2) 0.21631(6) 0.0311(3) Uani 1 1 d . . .
H3 H 0.4651 -0.2026 0.2174 0.037 Uiso 1 1 calc R . .
C4 C 0.1432(3) -0.0864(2) 0.17222(6) 0.0302(3) Uani 1 1 d . . .
H4 H 0.1495 -0.2148 0.1434 0.036 Uiso 1 1 calc R . .
C5 C -0.0559(2) 0.2604(2) 0.20933(5) 0.0274(3) Uani 1 1 d . . .
H5 H -0.1903 0.3806 0.2068 0.033 Uiso 1 1 calc R . .
C6 C 0.0921(2) 0.4811(2) 0.29932(5) 0.0253(2) Uani 1 1 d . . .
C7 C 0.4381(2) 0.2814(2) 0.08359(5) 0.0271(3) Uani 1 1 d . . .
C8 C 0.2385(3) 0.2716(2) 0.03474(5) 0.0294(3) Uani 1 1 d . . .
H8A H 0.1074 0.1312 0.0389 0.035 Uiso 1 1 calc R . .
H8B H 0.3336 0.2331 0.0004 0.035 Uiso 1 1 calc R . .
C9 C 0.0863(2) 0.5091(2) 0.02711(5) 0.0284(3) Uani 1 1 d . . .
H9A H 0.2150 0.6544 0.0268 0.034 Uiso 1 1 calc R . .
H9B H -0.0289 0.5376 0.0590 0.034 Uiso 1 1 calc R . .
C10 C -0.0486(3) 0.0642(2) 0.40374(5) 0.0307(3) Uani 1 1 d . . .
C11 C -0.1486(3) 0.2748(3) 0.43996(6) 0.0377(3) Uani 1 1 d . . .
H11A H -0.2985 0.2086 0.4610 0.045 Uiso 1 1 calc R . .
H11B H -0.2199 0.4033 0.4157 0.045 Uiso 1 1 calc R . .
C12 C 0.0599(3) 0.4001(2) 0.48100(5) 0.0326(3) Uani 1 1 d . . .
H12A H 0.2040 0.4788 0.4603 0.039 Uiso 1 1 calc R . .
H12B H 0.1401 0.2715 0.5041 0.039 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
O1 C6 1.2498(14) . ?
O2 C7 1.3263(14) . ?
O2 H2A 0.933(19) . ?
O3 C7 1.2131(15) . ?
O4 C10 1.3238(17) . ?
O4 H4A 0.89(2) . ?
O5 C10 1.2085(16) . ?
N1 C5 1.3389(16) . ?
N1 C4 1.3390(16) . ?
N2 C6 1.3237(16) . ?
N2 H2N1 0.8800 . ?
N2 H2N2 0.8800 . ?
C1 C5 1.3872(17) . ?
C1 C2 1.3912(16) . ?
C1 C6 1.4910(16) . ?
C2 C3 1.3871(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3826(19) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.5029(17) . ?
C8 C9 1.5186(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 1.526(2) 2_565 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5013(17) . ?
C11 C12 1.5130(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C12 1.526(2) 2_566 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C7 O2 H2A 111.0(10) . . ?
C10 O4 H4A 109.1(12) . . ?
C5 N1 C4 118.02(11) . . ?
C6 N2 H2N1 120.0 . . ?
C6 N2 H2N2 120.0 . . ?
H2N1 N2 H2N2 120.0 . . ?
C5 C1 C2 118.59(11) . . ?
C5 C1 C6 118.58(10) . . ?
C2 C1 C6 122.82(11) . . ?
C3 C2 C1 118.59(12) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 118.96(11) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N1 C4 C3 122.89(11) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
N1 C5 C1 122.94(11) . . ?
N1 C5 H5 118.5 . . ?
C1 C5 H5 118.5 . . ?
O1 C6 N2 121.97(11) . . ?
O1 C6 C1 119.73(11) . . ?
N2 C6 C1 118.29(10) . . ?
O3 C7 O2 123.13(12) . . ?
O3 C7 C8 125.43(11) . . ?
O2 C7 C8 111.44(10) . . ?
C7 C8 C9 115.58(10) . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C9 111.42(12) . 2_565 ?
C8 C9 H9A 109.3 . . ?
C9 C9 H9A 109.3 2_565 . ?
C8 C9 H9B 109.3 . . ?
C9 C9 H9B 109.3 2_565 . ?
H9A C9 H9B 108.0 . . ?
O5 C10 O4 122.83(12) . . ?
O5 C10 C11 124.70(12) . . ?
O4 C10 C11 112.46(11) . . ?
C10 C11 C12 114.60(11) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C12 111.70(14) . 2_566 ?
C11 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 2_566 . ?
C11 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 2_566 . ?
H12A C12 H12B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -0.45(18) . . . . ?
C6 C1 C2 C3 178.89(12) . . . . ?
C1 C2 C3 C4 -0.24(19) . . . . ?
C5 N1 C4 C3 -0.57(19) . . . . ?
C2 C3 C4 N1 0.8(2) . . . . ?
C4 N1 C5 C1 -0.17(19) . . . . ?
C2 C1 C5 N1 0.68(19) . . . . ?
C6 C1 C5 N1 -178.69(11) . . . . ?
C5 C1 C6 O1 22.78(18) . . . . ?
C2 C1 C6 O1 -156.56(12) . . . . ?
C5 C1 C6 N2 -157.02(12) . . . . ?
C2 C1 C6 N2 23.64(18) . . . . ?
O3 C7 C8 C9 10.98(19) . . . . ?
O2 C7 C8 C9 -170.03(11) . . . . ?
C7 C8 C9 C9 173.36(13) . . . 2_565 ?
O5 C10 C11 C12 12.6(2) . . . . ?
O4 C10 C11 C12 -168.33(13) . . . . ?
C10 C11 C12 C12 -176.14(14) . . . 2_566 ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        29.10
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043

data_(na)2.(adi)
_database_code_depnum_ccdc_archive 'CCDC 695333'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:adipic acid 2:1
;
_chemical_name_common            'nicotinamide:adipic acid 2:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 O4, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.40

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0302(3)
_cell_length_b                   5.4600(3)
_cell_length_c                   16.9903(9)
_cell_angle_alpha                82.380(4)
_cell_angle_beta                 89.395(4)
_cell_angle_gamma                90.006(2)
_cell_volume                     462.49(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3300
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             206
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  1.008
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -OH hydrogen atom was located and its position was refined
satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            4351
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2176
_reflns_number_gt                1549
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0497P)²+0.1635P] 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         2176
_refine_ls_number_parameters     130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.8087(2) 0.8271(3) 0.43195(8) 0.0376(4) Uani 1 1 d . . .
O2 O 0.4281(3) 0.8420(3) 0.17017(8) 0.0449(4) Uani 1 1 d . . .
O3 O 0.5773(3) 0.5181(3) 0.11603(7) 0.0403(4) Uani 1 1 d D . .
H3A H 0.697(4) 0.499(4) 0.1612(11) 0.048 Uiso 1 1 d D . .
N1 N 0.9172(3) 0.4451(3) 0.23803(9) 0.0349(4) Uani 1 1 d . . .
N2 N 1.2428(3) 0.7905(3) 0.46255(8) 0.0328(4) Uani 1 1 d . . .
H2A H 1.2260 0.8871 0.4998 0.039 Uiso 1 1 calc R . .
H2B H 1.3986 0.7267 0.4531 0.039 Uiso 1 1 calc R . .
C1 C 1.1093(4) 0.2760(4) 0.24253(11) 0.0353(4) Uani 1 1 d . . .
H1 H 1.1209 0.1710 0.2023 0.042 Uiso 1 1 calc R . .
C2 C 1.2930(4) 0.2464(4) 0.30331(11) 0.0349(4) Uani 1 1 d . . .
H2 H 1.4283 0.1247 0.3045 0.042 Uiso 1 1 calc R . .
C3 C 1.2747(4) 0.3985(3) 0.36231(10) 0.0323(4) Uani 1 1 d . . .
H3 H 1.3989 0.3836 0.4044 0.039 Uiso 1 1 calc R . .
C4 C 1.0734(3) 0.5723(3) 0.35916(9) 0.0276(4) Uani 1 1 d . . .
C5 C 0.9006(4) 0.5901(3) 0.29531(10) 0.0318(4) Uani 1 1 d . . .
H5 H 0.7642 0.7113 0.2923 0.038 Uiso 1 1 calc R . .
C6 C 1.0328(3) 0.7410(3) 0.42059(10) 0.0287(4) Uani 1 1 d . . .
C7 C 0.4214(4) 0.7127(3) 0.11785(10) 0.0319(4) Uani 1 1 d . . .
C8 C 0.2361(4) 0.7458(4) 0.04855(10) 0.0349(4) Uani 1 1 d . . .
H8A H 0.1092 0.6058 0.0544 0.042 Uiso 1 1 calc R . .
H8B H 0.3413 0.7372 -0.0006 0.042 Uiso 1 1 calc R . .
C9 C 0.0791(4) 0.9842(3) 0.03843(10) 0.0331(4) Uani 1 1 d . . .
H9A H 0.2027 1.1254 0.0382 0.040 Uiso 1 1 calc R . .
H9B H -0.0446 0.9852 0.0841 0.040 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
O1 C6 1.244(2) . ?
O2 C7 1.207(2) . ?
O3 C7 1.324(2) . ?
O3 H3A 0.975(15) . ?
N1 C1 1.333(2) . ?
N1 C5 1.336(2) . ?
N2 C6 1.328(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C6 1.493(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.502(2) . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 1.527(3) 2_575 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C7 O3 H3A 110.7(13) . . ?
C1 N1 C5 118.13(15) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.92(16) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.50(17) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 119.23(16) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.07(15) . . ?
C3 C4 C6 123.43(15) . . ?
C5 C4 C6 118.50(15) . . ?
N1 C5 C4 123.14(16) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 122.21(15) . . ?
O1 C6 C4 120.41(15) . . ?
N2 C6 C4 117.37(15) . . ?
O2 C7 O3 123.09(16) . . ?
O2 C7 C8 125.33(17) . . ?
O3 C7 C8 111.57(14) . . ?
C7 C8 C9 115.50(15) . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C9 111.86(18) . 2_575 ?
C8 C9 H9A 109.2 . . ?
C9 C9 H9A 109.2 2_575 . ?
C8 C9 H9B 109.2 . . ?
C9 C9 H9B 109.2 2_575 . ?
H9A C9 H9B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.7(3) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C6 178.64(16) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C3 C4 C5 N1 1.2(3) . . . . ?
C6 C4 C5 N1 -178.84(16) . . . . ?
C3 C4 C6 O1 -154.23(18) . . . . ?
C5 C4 C6 O1 25.8(3) . . . . ?
C3 C4 C6 N2 24.7(3) . . . . ?
C5 C4 C6 N2 -155.19(17) . . . . ?
O2 C7 C8 C9 10.1(3) . . . . ?
O3 C7 C8 C9 -171.14(16) . . . . ?
C7 C8 C9 C9 173.42(19) . . . 2_575 ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047

data_(na).(pim)
_database_code_depnum_ccdc_archive 'CCDC 695334'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:pimelic acid 1:1
;
_chemical_name_common            'nicotinamide:pimelic acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H12 O4, C6 H6 N2 O'
_chemical_formula_sum            'C13 H18 N2 O5'
_chemical_formula_weight         282.29

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.4425(1)
_cell_length_b                   7.3981(2)
_cell_length_c                   17.9304(6)
_cell_angle_alpha                99.568(2)
_cell_angle_beta                 94.075(2)
_cell_angle_gamma                104.177(2)
_cell_volume                     685.49(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4820
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions were
refined satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            6741
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2390
_reflns_number_gt                2156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0494P)²+0.1547P] 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         2390
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
O1 O 0.84889(17) 0.67931(13) -0.01703(5) 0.0352(2) Uani 1 1 d . . .
O2 O 0.12418(17) 0.24623(13) 0.15366(5) 0.0347(2) Uani 1 1 d . . .
H21 H 0.116(3) 0.257(2) 0.1048(10) 0.042 Uiso 1 1 d . . .
O3 O -0.27450(17) 0.06694(13) 0.12325(5) 0.0356(2) Uani 1 1 d . . .
O4 O 0.76909(17) 0.31321(15) 0.56772(5) 0.0405(3) Uani 1 1 d . . .
O5 O 0.47908(19) 0.21731(15) 0.64443(5) 0.0398(3) Uani 1 1 d . . .
H51 H 0.616(3) 0.243(2) 0.6788(11) 0.048 Uiso 1 1 d . . .
N1 N 1.1312(2) 0.70168(15) 0.24309(6) 0.0289(3) Uani 1 1 d . . .
N2 N 1.2447(2) 0.85115(19) 0.02929(7) 0.0474(4) Uani 1 1 d . . .
H2A H 1.2737 0.8840 -0.0149 0.057 Uiso 1 1 calc R . .
H2B H 1.3643 0.8924 0.0683 0.057 Uiso 1 1 calc R . .
C1 C 0.8990(2) 0.60365(17) 0.25303(7) 0.0295(3) Uani 1 1 d . . .
H1 H 0.8700 0.5759 0.3020 0.035 Uiso 1 1 calc R . .
C2 C 0.6984(2) 0.54065(18) 0.19505(7) 0.0311(3) Uani 1 1 d . . .
H2 H 0.5361 0.4697 0.2040 0.037 Uiso 1 1 calc R . .
C3 C 0.7390(2) 0.58307(17) 0.12385(7) 0.0290(3) Uani 1 1 d . . .
H3 H 0.6051 0.5406 0.0830 0.035 Uiso 1 1 calc R . .
C4 C 0.9784(2) 0.68865(16) 0.11294(7) 0.0252(3) Uani 1 1 d . . .
C5 C 1.1685(2) 0.74357(17) 0.17427(7) 0.0274(3) Uani 1 1 d . . .
H5 H 1.3331 0.8143 0.1670 0.033 Uiso 1 1 calc R . .
C6 C 1.0223(2) 0.74026(17) 0.03694(7) 0.0275(3) Uani 1 1 d . . .
C7 C -0.0893(2) 0.14259(16) 0.17048(7) 0.0257(3) Uani 1 1 d . . .
C8 C -0.0899(2) 0.12502(17) 0.25275(7) 0.0278(3) Uani 1 1 d . . .
H8A H -0.1562 -0.0110 0.2548 0.033 Uiso 1 1 calc R . .
H8B H -0.2119 0.1923 0.2749 0.033 Uiso 1 1 calc R . .
C9 C 0.1639(2) 0.20010(17) 0.30329(7) 0.0281(3) Uani 1 1 d . . .
H9A H 0.2301 0.3376 0.3040 0.034 Uiso 1 1 calc R . .
H9B H 0.2893 0.1348 0.2821 0.034 Uiso 1 1 calc R . .
C10 C 0.1331(2) 0.16784(19) 0.38427(7) 0.0313(3) Uani 1 1 d . . .
H10A H 0.0109 0.2366 0.4052 0.038 Uiso 1 1 calc R . .
H10B H 0.0580 0.0308 0.3824 0.038 Uiso 1 1 calc R . .
C11 C 0.3788(2) 0.23131(18) 0.43826(7) 0.0285(3) Uani 1 1 d . . .
H11A H 0.4566 0.3683 0.4408 0.034 Uiso 1 1 calc R . .
H11B H 0.5013 0.1605 0.4191 0.034 Uiso 1 1 calc R . .
C12 C 0.3244(2) 0.19551(19) 0.51739(7) 0.0306(3) Uani 1 1 d . . .
H12A H 0.2000 0.2661 0.5350 0.037 Uiso 1 1 calc R . .
H12B H 0.2419 0.0586 0.5132 0.037 Uiso 1 1 calc R . .
C13 C 0.5502(2) 0.24979(17) 0.57715(7) 0.0267(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2438(15) . ?
O2 C7 1.3110(15) . ?
O2 H21 0.893(18) . ?
O3 C7 1.2213(15) . ?
O4 C13 1.2040(15) . ?
O5 C13 1.3341(15) . ?
O5 H51 0.891(19) . ?
N1 C1 1.3347(16) . ?
N1 C5 1.3385(16) . ?
N2 C6 1.3157(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.3849(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3844(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3910(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3888(17) . ?
C4 C6 1.4948(17) . ?
C5 H5 0.9500 . ?
C7 C8 1.5023(16) . ?
C8 C9 1.5222(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5244(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5176(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5222(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4989(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C7 O2 H21 112.6(10) . . ?
C13 O5 H51 110.2(11) . . ?
C1 N1 C5 118.08(11) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.86(11) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.73(12) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.13(11) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 117.97(11) . . ?
C5 C4 C6 122.43(11) . . ?
C3 C4 C6 119.60(11) . . ?
N1 C5 C4 123.21(11) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 121.72(11) . . ?
O1 C6 C4 119.66(11) . . ?
N2 C6 C4 118.62(11) . . ?
O3 C7 O2 122.83(11) . . ?
O3 C7 C8 122.32(11) . . ?
O2 C7 C8 114.85(10) . . ?
C7 C8 C9 117.13(10) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 110.84(10) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 114.67(10) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 110.04(10) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 116.28(11) . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
O4 C13 O5 122.82(12) . . ?
O4 C13 C12 126.14(11) . . ?
O5 C13 C12 111.03(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.42(18) . . . . ?
N1 C1 C2 C3 -0.87(19) . . . . ?
C1 C2 C3 C4 -0.54(18) . . . . ?
C2 C3 C4 C5 1.31(17) . . . . ?
C2 C3 C4 C6 -178.18(11) . . . . ?
C1 N1 C5 C4 -0.57(18) . . . . ?
C3 C4 C5 N1 -0.79(18) . . . . ?
C6 C4 C5 N1 178.69(11) . . . . ?
C5 C4 C6 O1 176.45(11) . . . . ?
C3 C4 C6 O1 -4.09(18) . . . . ?
C5 C4 C6 N2 -4.11(18) . . . . ?
C3 C4 C6 N2 175.36(12) . . . . ?
O3 C7 C8 C9 170.95(11) . . . . ?
O2 C7 C8 C9 -9.54(16) . . . . ?
C7 C8 C9 C10 -178.65(10) . . . . ?
C8 C9 C10 C11 177.71(10) . . . . ?
C9 C10 C11 C12 179.02(10) . . . . ?
C10 C11 C12 C13 179.52(10) . . . . ?
C11 C12 C13 O4 -2.34(19) . . . . ?
C11 C12 C13 O5 178.20(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.035

data_(na).(sub)
_database_code_depnum_ccdc_archive 'CCDC 695335'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:suberic acid 1:1
;
_chemical_name_common            'nicotinamide:suberic acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C8 H14 O4'
_chemical_formula_sum            'C14 H20 N2 O5'
_chemical_formula_weight         296.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   4.95370(10)
_cell_length_b                   35.2893(6)
_cell_length_c                   8.7180(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8320(10)
_cell_angle_gamma                90.00
_cell_volume                     1518.60(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    16782
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      17.68

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
Poor (weakly diffracting) crystals: theta(max)=17.68deg.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            4592
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         17.68
_reflns_number_total             982
_reflns_number_gt                898
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0446P)²+0.3752P] 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         982
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0734
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O1 O 0.8745(4) 0.30154(4) 0.5036(2) 0.0333(5) Uani 1 1 d . . .
O2 O 1.1089(3) 0.33107(6) 0.8417(2) 0.0383(6) Uani 1 1 d . . .
O3 O 0.8785(4) 0.36826(5) 0.9903(2) 0.0427(6) Uani 1 1 d . . .
H3A H 0.796(5) 0.3439(8) 1.024(3) 0.051 Uiso 1 1 d . . .
O4 O 0.9483(4) 0.63639(7) 0.6097(2) 0.0468(6) Uani 1 1 d . . .
H4A H 1.019(5) 0.6576(8) 0.563(3) 0.056 Uiso 1 1 d . . .
O5 O 1.2895(4) 0.60294(5) 0.5314(2) 0.0541(7) Uani 1 1 d . . .
N1 N 0.6526(5) 0.19219(8) 0.5935(3) 0.0291(6) Uani 1 1 d . . .
N2 N 0.5293(4) 0.32696(7) 0.6187(2) 0.0344(6) Uani 1 1 d . . .
H2A H 0.5740 0.3500 0.5915 0.041 Uiso 1 1 calc R . .
H2B H 0.3884 0.3235 0.6722 0.041 Uiso 1 1 calc R . .
C1 C 0.4559(7) 0.18632(8) 0.6866(4) 0.0309(8) Uani 1 1 d . . .
H1 H 0.4096 0.1609 0.7095 0.037 Uiso 1 1 calc R . .
C2 C 0.3175(5) 0.21516(11) 0.7510(3) 0.0291(7) Uani 1 1 d . . .
H2 H 0.1782 0.2098 0.8162 0.035 Uiso 1 1 calc R . .
C3 C 0.3840(6) 0.25192(10) 0.7193(3) 0.0272(7) Uani 1 1 d . . .
H3 H 0.2906 0.2723 0.7623 0.033 Uiso 1 1 calc R . .
C4 C 0.5887(6) 0.25907(9) 0.6239(3) 0.0220(7) Uani 1 1 d . . .
C5 C 0.7155(5) 0.22805(12) 0.5635(3) 0.0274(7) Uani 1 1 d . . .
H5 H 0.8547 0.2326 0.4972 0.033 Uiso 1 1 calc R . .
C6 C 0.6733(6) 0.29770(9) 0.5794(3) 0.0255(7) Uani 1 1 d . . .
C7 C 1.0551(6) 0.36262(10) 0.8883(4) 0.0311(8) Uani 1 1 d . . .
C8 C 1.1882(5) 0.39811(8) 0.8376(3) 0.0415(8) Uani 1 1 d . . .
H8A H 1.2537 0.3934 0.7351 0.050 Uiso 1 1 calc R . .
H8B H 1.3491 0.4031 0.9100 0.050 Uiso 1 1 calc R . .
C9 C 1.0147(5) 0.43351(7) 0.8273(3) 0.0371(8) Uani 1 1 d . . .
H9A H 0.9519 0.4389 0.9299 0.044 Uiso 1 1 calc R . .
H9B H 0.8526 0.4288 0.7554 0.044 Uiso 1 1 calc R . .
C10 C 1.1632(5) 0.46801(8) 0.7729(3) 0.0428(8) Uani 1 1 d . . .
H10A H 1.3207 0.4733 0.8475 0.051 Uiso 1 1 calc R . .
H10B H 1.2335 0.4621 0.6727 0.051 Uiso 1 1 calc R . .
C11 C 0.9904(5) 0.50336(7) 0.7549(3) 0.0401(8) Uani 1 1 d . . .
H11A H 0.9286 0.5102 0.8564 0.048 Uiso 1 1 calc R . .
H11B H 0.8277 0.4977 0.6848 0.048 Uiso 1 1 calc R . .
C12 C 1.1358(5) 0.53713(7) 0.6923(3) 0.0407(8) Uani 1 1 d . . .
H12A H 1.3002 0.5426 0.7613 0.049 Uiso 1 1 calc R . .
H12B H 1.1945 0.5306 0.5898 0.049 Uiso 1 1 calc R . .
C13 C 0.9616(5) 0.57240(8) 0.6776(3) 0.0381(8) Uani 1 1 d . . .
H13A H 0.7877 0.5660 0.6191 0.046 Uiso 1 1 calc R . .
H13B H 0.9205 0.5805 0.7819 0.046 Uiso 1 1 calc R . .
C14 C 1.0868(8) 0.60482(9) 0.6002(3) 0.0331(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.249(3) . ?
O2 C7 1.222(3) . ?
O3 C7 1.314(3) . ?
O3 H3A 1.01(3) . ?
O4 C14 1.315(3) . ?
O4 H4A 0.93(3) . ?
O5 C14 1.214(3) . ?
N1 C5 1.334(3) . ?
N1 C1 1.336(3) . ?
N2 C6 1.317(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.373(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 C6 1.487(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.499(4) . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.513(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.490(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C7 O3 H3A 112.2(14) . . ?
C14 O4 H4A 115.7(17) . . ?
C5 N1 C1 117.4(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 123.2(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 117.5(2) . . ?
C3 C4 C6 124.0(3) . . ?
C5 C4 C6 118.5(3) . . ?
N1 C5 C4 123.6(2) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1 C6 N2 121.8(3) . . ?
O1 C6 C4 119.5(3) . . ?
N2 C6 C4 118.7(3) . . ?
O2 C7 O3 122.6(3) . . ?
O2 C7 C8 123.3(3) . . ?
O3 C7 C8 114.0(3) . . ?
C7 C8 C9 116.4(2) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 113.1(2) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.1(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 113.8(2) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.0(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O5 C14 O4 122.4(3) . . ?
O5 C14 C13 125.1(3) . . ?
O4 C14 C13 112.5(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.3(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C4 C6 178.7(2) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C6 C4 C5 N1 -178.8(2) . . . . ?
C3 C4 C6 O1 174.0(2) . . . . ?
C5 C4 C6 O1 -7.9(3) . . . . ?
C3 C4 C6 N2 -7.4(3) . . . . ?
C5 C4 C6 N2 170.7(2) . . . . ?
O2 C7 C8 C9 146.7(2) . . . . ?
O3 C7 C8 C9 -34.6(3) . . . . ?
C7 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C11 177.4(2) . . . . ?
C9 C10 C11 C12 -176.9(2) . . . . ?
C10 C11 C12 C13 -179.0(2) . . . . ?
C11 C12 C13 C14 -173.4(2) . . . . ?
C12 C13 C14 O5 11.3(4) . . . . ?
C12 C13 C14 O4 -170.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        17.68
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.026

data_(na)2.(sub)
_database_code_depnum_ccdc_archive 'CCDC 695336'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:suberic acid 2:1
;
_chemical_name_common            'nicotinamide:suberic acid 2:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 O4, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C20 H26 N4 O6'
_chemical_formula_weight         418.45

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0288(3)
_cell_length_b                   5.4403(3)
_cell_length_c                   18.7537(11)
_cell_angle_alpha                93.062(3)
_cell_angle_beta                 94.810(3)
_cell_angle_gamma                90.740(2)
_cell_volume                     510.45(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7216
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      30.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             222
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atom was located and its position was refined
satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            6237
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         29.90
_reflns_number_total             2848
_reflns_number_gt                1495
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0390P)²+0.4980P] 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         2848
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.3238(4) 0.8094(4) 0.06122(10) 0.0346(5) Uani 1 1 d . . .
N1 N 0.4762(5) 0.3822(4) 0.23700(12) 0.0338(6) Uani 1 1 d . . .
C1 C 0.6664(6) 0.2140(5) 0.23297(15) 0.0339(7) Uani 1 1 d . . .
H1 H 0.6875 0.0996 0.2695 0.041 Uiso 1 1 calc R . .
O2 O 0.1720(4) 0.4321(4) 0.34786(11) 0.0402(6) Uani 1 1 d . . .
H2C H 0.268(7) 0.414(6) 0.3054(18) 0.048 Uiso 1 1 d . . .
N2 N 0.7489(4) 0.7813(4) 0.03355(12) 0.0319(6) Uani 1 1 d . . .
H2A H 0.7240 0.8878 0.0000 0.038 Uiso 1 1 calc R . .
H2B H 0.9065 0.7152 0.0420 0.038 Uiso 1 1 calc R . .
C2 C 0.8330(6) 0.1991(5) 0.17841(15) 0.0320(7) Uani 1 1 d . . .
H2 H 0.9673 0.0780 0.1776 0.038 Uiso 1 1 calc R . .
O3 O 0.0027(4) 0.7642(4) 0.29671(11) 0.0427(6) Uani 1 1 d . . .
C3 C 0.8015(5) 0.3630(5) 0.12484(14) 0.0288(6) Uani 1 1 d . . .
H3 H 0.9141 0.3560 0.0866 0.035 Uiso 1 1 calc R . .
C4 C 0.6037(5) 0.5382(5) 0.12731(14) 0.0252(6) Uani 1 1 d . . .
C5 C 0.4468(5) 0.5417(5) 0.18487(14) 0.0303(6) Uani 1 1 d . . .
H5 H 0.3127 0.6625 0.1875 0.036 Uiso 1 1 calc R . .
C6 C 0.5484(5) 0.7202(5) 0.07154(14) 0.0277(6) Uani 1 1 d . . .
C7 C 0.0131(6) 0.6239(5) 0.34517(15) 0.0323(7) Uani 1 1 d . . .
C8 C -0.1492(6) 0.6428(6) 0.40875(16) 0.0381(7) Uani 1 1 d . . .
H8A H -0.0287 0.6184 0.4522 0.046 Uiso 1 1 calc R . .
H8B H -0.2815 0.5053 0.4039 0.046 Uiso 1 1 calc R . .
C9 C -0.2966(6) 0.8793(5) 0.42075(15) 0.0345(7) Uani 1 1 d . . .
H9A H -0.4348 0.8969 0.3806 0.041 Uiso 1 1 calc R . .
H9B H -0.1702 1.0207 0.4218 0.041 Uiso 1 1 calc R . .
C10 C -0.4284(6) 0.8815(5) 0.49129(16) 0.0361(7) Uani 1 1 d . . .
H10A H -0.5583 0.7424 0.4891 0.043 Uiso 1 1 calc R . .
H10B H -0.2899 0.8548 0.5307 0.043 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
O1 C6 1.239(3) . ?
N1 C1 1.336(4) . ?
N1 C5 1.342(3) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
O2 C7 1.323(3) . ?
O2 H2C 0.97(3) . ?
N2 C6 1.331(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
O3 C7 1.216(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 C6 1.490(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.500(4) . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.528(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C10 1.518(6) 2_476 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.0(2) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C7 O2 H2C 111.3(19) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 C6 123.9(2) . . ?
C5 C4 C6 118.3(2) . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 121.8(2) . . ?
O1 C6 C4 120.8(2) . . ?
N2 C6 C4 117.3(2) . . ?
O3 C7 O2 123.4(3) . . ?
O3 C7 C8 125.3(3) . . ?
O2 C7 C8 111.3(2) . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 110.8(2) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C10 C9 114.0(3) 2_476 . ?
C10 C10 H10A 108.8 2_476 . ?
C9 C10 H10A 108.8 . . ?
C10 C10 H10B 108.8 2_476 . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.5(4) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 C6 -178.6(3) . . . . ?
C1 N1 C5 C4 0.3(4) . . . . ?
C3 C4 C5 N1 -0.9(4) . . . . ?
C6 C4 C5 N1 178.4(2) . . . . ?
C3 C4 C6 O1 154.0(3) . . . . ?
C5 C4 C6 O1 -25.3(4) . . . . ?
C3 C4 C6 N2 -25.8(4) . . . . ?
C5 C4 C6 N2 154.9(3) . . . . ?
O3 C7 C8 C9 -12.3(5) . . . . ?
O2 C7 C8 C9 167.9(3) . . . . ?
C7 C8 C9 C10 -174.1(3) . . . . ?
C8 C9 C10 C10 177.6(3) . . . 2_476 ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        29.90
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067

data_(na).(aze)
_database_code_depnum_ccdc_archive 'CCDC 695337'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:azelaic acid 2:1
;
_chemical_name_common            'nicotinamide:azelaic acid 2:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 N2 O, C9 H16 O4'
_chemical_formula_sum            'C15 H22 N2 O5'
_chemical_formula_weight         310.35
_chemical_absolute_configuration 
;
1133 Friedel pairs were averaged for the refinement.
;

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   8.64550(10)
_cell_length_b                   36.5695(6)
_cell_length_c                   5.20210(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1644.70(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    23872
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -COOH hydrogen atoms were located and their positions were
refinede satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            10952
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2082
_reflns_number_gt                1620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0489P)²+0.3144P] 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         2082
_refine_ls_number_parameters     205
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
O1 O 0.5529(2) 0.29892(4) 1.7504(4) 0.0482(5) Uani 1 1 d . . .
O2 O 0.8911(2) 0.32755(5) 0.9865(4) 0.0569(5) Uani 1 1 d . . .
O3 O 1.0730(2) 0.36331(5) 0.8246(4) 0.0591(6) Uani 1 1 d . . .
H3A H 1.099(3) 0.3397(8) 0.699(8) 0.071 Uiso 1 1 d . . .
O4 O 0.5358(2) 0.63839(5) 1.4411(4) 0.0567(6) Uani 1 1 d . . .
H4A H 0.501(3) 0.6583(8) 1.365(7) 0.068 Uiso 1 1 d . . .
O5 O 0.4916(3) 0.61078(5) 1.0708(5) 0.0814(8) Uani 1 1 d . . .
N1 N 0.6523(2) 0.19274(5) 1.5445(4) 0.0427(5) Uani 1 1 d . . .
N2 N 0.6582(3) 0.32234(6) 1.3924(5) 0.0508(6) Uani 1 1 d . . .
H2A H 0.6297 0.3446 1.4347 0.061 Uiso 1 1 calc R . .
H2B H 0.7091 0.3185 1.2484 0.061 Uiso 1 1 calc R . .
C1 C 0.6173(3) 0.22752(6) 1.6029(5) 0.0402(6) Uani 1 1 d . . .
H1 H 0.5520 0.2320 1.7463 0.048 Uiso 1 1 calc R . .
C2 C 0.6717(2) 0.25702(6) 1.4645(5) 0.0354(5) Uani 1 1 d . . .
C3 C 0.7644(3) 0.25031(7) 1.2537(6) 0.0427(6) Uani 1 1 d . . .
H3 H 0.8025 0.2700 1.1524 0.051 Uiso 1 1 calc R . .
C4 C 0.8013(3) 0.21440(7) 1.1918(6) 0.0471(7) Uani 1 1 d . . .
H4 H 0.8653 0.2091 1.0482 0.057 Uiso 1 1 calc R . .
C5 C 0.7436(3) 0.18687(7) 1.3421(5) 0.0446(6) Uani 1 1 d . . .
H5 H 0.7699 0.1624 1.3001 0.053 Uiso 1 1 calc R . .
C6 C 0.6248(3) 0.29467(6) 1.5448(5) 0.0397(6) Uani 1 1 d . . .
C7 C 0.9621(3) 0.35611(7) 0.9877(6) 0.0484(7) Uani 1 1 d . . .
C8 C 0.9335(4) 0.38615(7) 1.1786(7) 0.0622(9) Uani 1 1 d . . .
H8A H 1.0316 0.3919 1.2681 0.075 Uiso 1 1 calc R . .
H8B H 0.8588 0.3774 1.3091 0.075 Uiso 1 1 calc R . .
C9 C 0.8717(3) 0.42045(7) 1.0568(7) 0.0595(8) Uani 1 1 d . . .
H9A H 0.7771 0.4145 0.9584 0.071 Uiso 1 1 calc R . .
H9B H 0.9493 0.4301 0.9345 0.071 Uiso 1 1 calc R . .
C10 C 0.8338(3) 0.44995(7) 1.2552(7) 0.0571(8) Uani 1 1 d . . .
H10A H 0.7563 0.4402 1.3773 0.068 Uiso 1 1 calc R . .
H10B H 0.9285 0.4557 1.3540 0.068 Uiso 1 1 calc R . .
C11 C 0.7717(4) 0.48484(7) 1.1384(7) 0.0646(9) Uani 1 1 d . . .
H11A H 0.6792 0.4789 1.0345 0.078 Uiso 1 1 calc R . .
H11B H 0.8507 0.4950 1.0206 0.078 Uiso 1 1 calc R . .
C12 C 0.7284(3) 0.51397(6) 1.3327(7) 0.0528(7) Uani 1 1 d . . .
H12A H 0.6533 0.5035 1.4561 0.063 Uiso 1 1 calc R . .
H12B H 0.8221 0.5210 1.4305 0.063 Uiso 1 1 calc R . .
C13 C 0.6590(4) 0.54794(7) 1.2139(7) 0.0567(8) Uani 1 1 d . . .
H13A H 0.7332 0.5580 1.0871 0.068 Uiso 1 1 calc R . .
H13B H 0.5641 0.5410 1.1196 0.068 Uiso 1 1 calc R . .
C14 C 0.6189(3) 0.57764(6) 1.4039(6) 0.0474(7) Uani 1 1 d . . .
H14A H 0.5490 0.5673 1.5361 0.057 Uiso 1 1 calc R . .
H14B H 0.7147 0.5856 1.4916 0.057 Uiso 1 1 calc R . .
C15 C 0.5428(3) 0.61031(6) 1.2854(6) 0.0449(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.246(3) . ?
O2 C7 1.211(3) . ?
O3 C7 1.307(3) . ?
O3 H3A 1.11(3) . ?
O4 C15 1.309(3) . ?
O4 H4A 0.88(3) . ?
O5 C15 1.201(4) . ?
N1 C5 1.334(3) . ?
N1 C1 1.342(3) . ?
N2 C6 1.317(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.380(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(4) . ?
C2 C6 1.495(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.501(4) . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.512(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.512(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.509(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.496(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
C7 O3 H3A 112.0(16) . . ?
C15 O4 H4A 113(2) . . ?
C5 N1 C1 117.7(2) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 C6 118.8(2) . . ?
C3 C2 C6 122.9(2) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
O1 C6 N2 122.0(2) . . ?
O1 C6 C2 119.3(2) . . ?
N2 C6 C2 118.7(2) . . ?
O2 C7 O3 122.8(3) . . ?
O2 C7 C8 123.4(3) . . ?
O3 C7 C8 113.7(2) . . ?
C7 C8 C9 113.0(3) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 112.4(3) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 113.6(3) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 114.4(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 113.8(3) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 114.5(3) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 113.9(3) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
O5 C15 O4 123.1(2) . . ?
O5 C15 C14 123.8(2) . . ?
O4 C15 C14 113.1(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.3(4) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
N1 C1 C2 C6 179.6(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C6 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C1 C2 C6 O1 8.2(4) . . . . ?
C3 C2 C6 O1 -173.4(2) . . . . ?
C1 C2 C6 N2 -170.5(2) . . . . ?
C3 C2 C6 N2 8.0(4) . . . . ?
O2 C7 C8 C9 -114.7(3) . . . . ?
O3 C7 C8 C9 66.3(4) . . . . ?
C7 C8 C9 C10 176.4(2) . . . . ?
C8 C9 C10 C11 179.8(3) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C10 C11 C12 C13 -177.1(3) . . . . ?
C11 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 -177.0(2) . . . . ?
C13 C14 C15 O5 13.2(4) . . . . ?
C13 C14 C15 O4 -167.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034

data_(na)2.(seb)
_database_code_depnum_ccdc_archive 'CCDC 695338'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
nicotinamide:sebacic acid 2:1
;
_chemical_name_common            'nicotinamide:sebacic acid 2:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 O4, 2(C6 H6 O2 N)'
_chemical_formula_sum            'C22 H30 N4 O6'
_chemical_formula_weight         446.50

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0365(2)
_cell_length_b                   5.4470(2)
_cell_length_c                   20.5004(9)
_cell_angle_alpha                89.354(2)
_cell_angle_beta                 84.241(2)
_cell_angle_gamma                89.872(2)
_cell_volume                     559.53(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7012
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             238
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
The -OH hydrogen atom was located and its position was refined
satisfactorily.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            5593
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2529
_reflns_number_gt                1906
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0427P)²+0.2549P] 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         2529
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O1 O 0.7843(2) 0.7969(2) 0.05643(6) 0.0391(3) Uani 1 1 d . . .
O2 O 0.4426(3) 0.3510(3) 0.31871(6) 0.0462(4) Uani 1 1 d . . .
H2C H 0.577(5) 0.351(4) 0.2820(11) 0.055 Uiso 1 1 d . . .
O3 O 0.3062(3) 0.6954(3) 0.27232(6) 0.0488(4) Uani 1 1 d . . .
N1 N 0.8225(3) 0.3287(3) 0.21691(7) 0.0382(4) Uani 1 1 d . . .
N2 N 1.2293(3) 0.7742(3) 0.03105(7) 0.0345(3) Uani 1 1 d . . .
H2A H 1.2262 0.8880 0.0003 0.041 Uiso 1 1 calc R . .
H2B H 1.3816 0.7058 0.0388 0.041 Uiso 1 1 calc R . .
C1 C 1.0181(4) 0.1607(3) 0.21321(9) 0.0375(4) Uani 1 1 d . . .
H1 H 1.0160 0.0379 0.2465 0.045 Uiso 1 1 calc R . .
C2 C 1.2221(4) 0.1587(3) 0.16308(9) 0.0371(4) Uani 1 1 d . . .
H2 H 1.3585 0.0377 0.1622 0.044 Uiso 1 1 calc R . .
C3 C 1.2252(3) 0.3359(3) 0.11405(8) 0.0338(4) Uani 1 1 d . . .
H3 H 1.3640 0.3386 0.0791 0.041 Uiso 1 1 calc R . .
C4 C 1.0220(3) 0.5099(3) 0.11678(8) 0.0290(4) Uani 1 1 d . . .
C5 C 0.8266(3) 0.4988(3) 0.16937(8) 0.0341(4) Uani 1 1 d . . .
H5 H 0.6884 0.6183 0.1717 0.041 Uiso 1 1 calc R . .
C6 C 1.0031(3) 0.7052(3) 0.06582(8) 0.0296(4) Uani 1 1 d . . .
C7 C 0.2848(4) 0.5456(3) 0.31641(8) 0.0350(4) Uani 1 1 d . . .
C8 C 0.0770(4) 0.5505(3) 0.37427(9) 0.0416(5) Uani 1 1 d . . .
H8A H 0.1656 0.5125 0.4142 0.050 Uiso 1 1 calc R . .
H8B H -0.0523 0.4172 0.3691 0.050 Uiso 1 1 calc R . .
C9 C -0.0776(4) 0.7878(3) 0.38554(9) 0.0376(4) Uani 1 1 d . . .
H9A H -0.1879 0.8172 0.3489 0.045 Uiso 1 1 calc R . .
H9B H 0.0489 0.9263 0.3865 0.045 Uiso 1 1 calc R . .
C10 C -0.2569(4) 0.7774(3) 0.44985(9) 0.0409(4) Uani 1 1 d . . .
H10A H -0.3855 0.6413 0.4476 0.049 Uiso 1 1 calc R . .
H10B H -0.1451 0.7373 0.4856 0.049 Uiso 1 1 calc R . .
C11 C -0.4120(4) 1.0098(3) 0.46770(8) 0.0396(4) Uani 1 1 d . . .
H11A H -0.5253 1.0505 0.4323 0.047 Uiso 1 1 calc R . .
H11B H -0.2845 1.1466 0.4704 0.047 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
O1 C6 1.2406(19) . ?
O2 C7 1.327(2) . ?
O2 H2C 0.96(2) . ?
O3 C7 1.208(2) . ?
N1 C5 1.336(2) . ?
N1 C1 1.340(2) . ?
N2 C6 1.334(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.379(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 C6 1.492(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.502(2) . ?
C8 C9 1.515(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.515(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C11 1.520(3) 2_476 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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
C7 O2 H2C 110.9(13) . . ?
C5 N1 C1 117.95(15) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.75(15) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.96(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.00(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 117.95(15) . . ?
C5 C4 C6 118.69(14) . . ?
C3 C4 C6 123.35(14) . . ?
N1 C5 C4 123.38(15) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
O1 C6 N2 122.06(15) . . ?
O1 C6 C4 120.65(14) . . ?
N2 C6 C4 117.29(14) . . ?
O3 C7 O2 123.37(16) . . ?
O3 C7 C8 125.24(16) . . ?
O2 C7 C8 111.37(14) . . ?
C7 C8 C9 116.66(15) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 111.00(14) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 115.57(15) . . ?
C11 C10 H10A 108.4 . . ?
C9 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C11 113.56(18) . 2_476 ?
C10 C11 H11A 108.9 . . ?
C11 C11 H11A 108.9 2_476 . ?
C10 C11 H11B 108.9 . . ?
C11 C11 H11B 108.9 2_476 . ?
H11A C11 H11B 107.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.7(3) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 C6 -178.66(16) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C3 C4 C5 N1 -0.7(3) . . . . ?
C6 C4 C5 N1 178.77(17) . . . . ?
C5 C4 C6 O1 -25.3(2) . . . . ?
C3 C4 C6 O1 154.08(18) . . . . ?
C5 C4 C6 N2 155.14(16) . . . . ?
C3 C4 C6 N2 -25.5(2) . . . . ?
O3 C7 C8 C9 -13.9(3) . . . . ?
O2 C7 C8 C9 167.34(17) . . . . ?
C7 C8 C9 C10 -173.31(17) . . . . ?
C8 C9 C10 C11 177.35(18) . . . . ?
C9 C10 C11 C11 180.0(2) . . . 2_476 ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044


