# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Andreas Lemmerer'
_publ_contact_author_email       ANDREAS.LEMMERER@GMAIL.COM

_publ_section_title              
;
Covalent Assistance to Supramolecular Synthesis:
The Use of Supramolecular Protecting Groups in Directing Hydrogen
;
_publ_requested_category         FO
loop_
_publ_author_name
'Andreas Lemmerer'
'Joel Bernstein'
'Volker Kahlenberg'

# Attachment 'Hydrazide_3-7.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 753783'
#TrackingRef 'Hydrazide_3-7.cif'

_audit_creation_date             2009-09-06T16:38:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(adipic acid).(nicotinic acid hydrazide)2
;
_chemical_formula_moiety         'C6 H10 O4, 2(C6 H7 N3 O)'
_chemical_formula_sum            'C18 H24 N6 O6'
_chemical_formula_weight         420.43

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1910(8)
_cell_length_b                   10.3449(5)
_cell_length_c                   7.4635(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.230(6)
_cell_angle_gamma                90
_cell_volume                     995.35(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3377
_cell_measurement_theta_min      3.1533
_cell_measurement_theta_max      28.2785

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.38
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_special_details           
;
Absorption corrections were made using the program Crysalis
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.97

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3822
_diffrn_measurement_device_type  
'Goniometer Xcalibur, detector: Ruby (Gemini ult'
_diffrn_measurement_method       '\w scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_number            6133
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             1840
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0312P)^2^+1.2612P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         1840
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_restrained_S_all      1.21
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6215(2) 0.3189(2) 0.6849(3) 0.0216(6) Uani 1 1 d . . .
C2 C 0.6566(2) 0.4408(3) 0.6470(4) 0.0265(6) Uani 1 1 d . . .
H2A H 0.6123 0.513 0.6486 0.032 Uiso 1 1 calc R . .
C3 C 0.8124(2) 0.3598(3) 0.6069(4) 0.0290(6) Uani 1 1 d . . .
H3 H 0.8788 0.3737 0.5801 0.035 Uiso 1 1 calc R . .
C4 C 0.7838(2) 0.2358(3) 0.6431(4) 0.0301(7) Uani 1 1 d . . .
H4 H 0.8303 0.1657 0.643 0.036 Uiso 1 1 calc R . .
C5 C 0.6868(2) 0.2149(3) 0.6794(4) 0.0260(6) Uani 1 1 d . . .
H5 H 0.665 0.1297 0.7004 0.031 Uiso 1 1 calc R . .
C6 C 0.51803(19) 0.2961(2) 0.7326(3) 0.0215(6) Uani 1 1 d . . .
N1 N 0.46838(17) 0.3993(2) 0.7775(3) 0.0269(6) Uani 1 1 d . . .
H1 H 0.495(2) 0.477(3) 0.778(4) 0.04 Uiso 1 1 d . . .
N2 N 0.74963(18) 0.4607(2) 0.6083(3) 0.0288(6) Uani 1 1 d . . .
N3 N 0.37064(19) 0.3909(2) 0.8272(4) 0.0305(6) Uani 1 1 d . . .
H3A H 0.379(3) 0.351(3) 0.928(5) 0.046 Uiso 1 1 d . . .
H3B H 0.331(3) 0.341(3) 0.744(5) 0.046 Uiso 1 1 d . . .
O1 O 0.48184(14) 0.18580(16) 0.7312(3) 0.0289(5) Uani 1 1 d . . .
C10 C 0.8747(2) 0.7426(2) 0.5347(4) 0.0224(6) Uani 1 1 d . . .
C11 C 0.8913(2) 0.8861(2) 0.5442(4) 0.0256(6) Uani 1 1 d . . .
H1A H 0.8953 0.9152 0.6719 0.031 Uiso 1 1 calc R . .
H11B H 0.8308 0.929 0.4658 0.031 Uiso 1 1 calc R . .
C12 C 0.9888(2) 0.9283(2) 0.4837(4) 0.0242(6) Uani 1 1 d . . .
H12A H 0.9813 0.9093 0.3516 0.029 Uiso 1 1 calc R . .
H12B H 1.0484 0.8777 0.5516 0.029 Uiso 1 1 calc R . .
O2 O 0.78285(15) 0.70924(19) 0.5666(3) 0.0364(6) Uani 1 1 d . . .
H2 H 0.781(3) 0.624(4) 0.568(5) 0.055 Uiso 1 1 d . . .
O3 O 0.93698(15) 0.66427(18) 0.5050(3) 0.0329(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0258(13) 0.0171(13) 0.0219(13) 0.0003(10) 0.0047(11) -0.0018(10)
C2 0.0279(14) 0.0184(13) 0.0338(15) -0.0007(11) 0.0076(12) -0.0013(11)
C3 0.0251(14) 0.0302(15) 0.0333(16) -0.0045(12) 0.0098(12) -0.0041(11)
C4 0.0294(15) 0.0248(15) 0.0385(17) -0.0040(12) 0.0123(13) 0.0046(12)
C5 0.0307(14) 0.0184(13) 0.0299(15) -0.0012(11) 0.0086(12) -0.0002(11)
C6 0.0242(13) 0.0160(12) 0.0237(14) 0.0026(10) 0.0034(11) -0.0015(11)
N1 0.0235(12) 0.0153(11) 0.0449(15) 0.0005(10) 0.0138(11) -0.0024(9)
N2 0.0302(12) 0.0212(12) 0.0376(14) -0.0023(10) 0.0129(11) -0.0067(10)
N3 0.0257(13) 0.0216(13) 0.0469(16) 0.0018(11) 0.0138(12) 0.0002(10)
O1 0.0283(10) 0.0141(10) 0.0464(12) 0.0014(8) 0.0123(9) -0.0016(8)
C10 0.0242(13) 0.0218(13) 0.0223(13) 0.0015(10) 0.0071(11) -0.0026(11)
C11 0.0274(14) 0.0180(13) 0.0328(15) 0.0015(11) 0.0098(12) -0.0033(11)
C12 0.0253(14) 0.0199(14) 0.0283(14) 0.0015(11) 0.0076(12) -0.0031(11)
O2 0.0303(11) 0.0175(10) 0.0670(16) 0.0003(10) 0.0226(11) -0.0044(9)
O3 0.0334(11) 0.0215(10) 0.0484(13) -0.0003(9) 0.0191(10) 0.0013(8)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C1 C5 1.385(4) . ?
C1 C2 1.393(3) . ?
C1 C6 1.500(3) . ?
C2 N2 1.335(3) . ?
C2 H2A 0.95 . ?
C3 N2 1.334(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.95 . ?
C4 C5 1.380(4) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.236(3) . ?
C6 N1 1.332(3) . ?
N1 N3 1.418(3) . ?
N1 H1 0.88(3) . ?
N3 H3A 0.85(4) . ?
N3 H3B 0.88(4) . ?
C10 O3 1.207(3) . ?
C10 O2 1.328(3) . ?
C10 C11 1.501(4) . ?
C11 C12 1.515(3) . ?
C11 H1A 0.99 . ?
C11 H11B 0.99 . ?
C12 C12 1.522(5) 3_776 ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
O2 H2 0.88(4) . ?

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
C5 C1 C2 117.5(2) . . ?
C5 C1 C6 119.2(2) . . ?
C2 C1 C6 123.3(2) . . ?
N2 C2 C1 123.0(2) . . ?
N2 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
N2 C3 C4 122.0(2) . . ?
N2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C1 119.5(2) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
O1 C6 N1 122.2(2) . . ?
O1 C6 C1 120.8(2) . . ?
N1 C6 C1 117.0(2) . . ?
C6 N1 N3 122.7(2) . . ?
C6 N1 H1 122(2) . . ?
N3 N1 H1 116(2) . . ?
C3 N2 C2 118.8(2) . . ?
N1 N3 H3A 108(2) . . ?
N1 N3 H3B 107(2) . . ?
H3A N3 H3B 106(3) . . ?
O3 C10 O2 122.7(2) . . ?
O3 C10 C11 125.0(2) . . ?
O2 C10 C11 112.2(2) . . ?
C10 C11 C12 113.3(2) . . ?
C10 C11 H1A 108.9 . . ?
C12 C11 H1A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H1A C11 H11B 107.7 . . ?
C11 C12 C12 112.4(3) . 3_776 ?
C11 C12 H12A 109.1 . . ?
C12 C12 H12A 109.1 3_776 . ?
C11 C12 H12B 109.1 . . ?
C12 C12 H12B 109.1 3_776 . ?
H12A C12 H12B 107.9 . . ?
C10 O2 H2 107(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 C1 C2 N2 -0.8(4) . . . . ?
C6 C1 C2 N2 178.6(2) . . . . ?
N2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C1 -2.2(4) . . . . ?
C2 C1 C5 C4 2.1(4) . . . . ?
C6 C1 C5 C4 -177.3(3) . . . . ?
C5 C1 C6 O1 -14.4(4) . . . . ?
C2 C1 C6 O1 166.2(3) . . . . ?
C5 C1 C6 N1 165.0(2) . . . . ?
C2 C1 C6 N1 -14.4(4) . . . . ?
O1 C6 N1 N3 0.1(4) . . . . ?
C1 C6 N1 N3 -179.3(3) . . . . ?
C4 C3 N2 C2 0.4(4) . . . . ?
C1 C2 N2 C3 -0.4(4) . . . . ?
O3 C10 C11 C12 9.0(4) . . . . ?
O2 C10 C11 C12 -172.3(2) . . . . ?
C10 C11 C12 C12 -173.0(3) . . . 3_776 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.88(4) 1.78(4) 2.638(3) 164(3) .
C3 H3 O3 0.95 3.18 3.705(3) 117 .
N1 H1 O1 0.88(3) 2.18(3) 3.040(3) 165(3) 2_656
N3 H3A O1 0.85(4) 2.41(4) 3.162(4) 148(3) 4_566
N3 H3B O2 0.88(4) 2.54(4) 3.360(4) 155(3) 3_666
_chemical_name_common            '(adipic acid).(nicotinic acid hydrazide)2'

### END

data_4
_database_code_depnum_ccdc_archive 'CCDC 753784'
#TrackingRef 'Hydrazide_3-7.cif'

_audit_creation_date             2009-09-14T11:34:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(adipic acid).((N'-(propan-2-ylidene)nicotinohydrazide)2
;
_chemical_formula_moiety         'C9 H11 N3 O, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C12 H16 N3 O3'
_chemical_formula_weight         250.28

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0880(2)
_cell_length_b                   38.9970(16)
_cell_length_c                   6.3470(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.128(4)
_cell_angle_gamma                90
_cell_volume                     1256.08(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3786
_cell_measurement_theta_min      3.1282
_cell_measurement_theta_max      27.752

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3822
_diffrn_measurement_device_type  
'Goniometer Xcalibur, detector: Ruby (Gemini ult'
_diffrn_measurement_method       '\w scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_number            6687
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2321
_reflns_number_gt                2014
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+2.6651P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2321
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.19
_refine_ls_restrained_S_all      1.19
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.7617(5) 0.36257(7) 0.5190(4) 0.0180(6) Uani 1 1 d . . .
C2 C 0.5501(5) 0.38395(7) 0.5562(4) 0.0189(6) Uani 1 1 d . . .
H2A H 0.47 0.3818 0.6862 0.023 Uiso 1 1 calc R . .
C3 C 0.5694(6) 0.41050(8) 0.2344(5) 0.0258(7) Uani 1 1 d . . .
H3 H 0.5003 0.4268 0.1337 0.031 Uiso 1 1 calc R . .
C4 C 0.7845(6) 0.39095(8) 0.1868(5) 0.0255(7) Uani 1 1 d . . .
H4 H 0.8632 0.394 0.0568 0.031 Uiso 1 1 calc R . .
C5 C 0.8821(6) 0.36701(7) 0.3317(5) 0.0231(6) Uani 1 1 d . . .
H5 H 1.0313 0.3536 0.3034 0.028 Uiso 1 1 calc R . .
C6 C 0.8711(5) 0.33643(7) 0.6723(4) 0.0185(6) Uani 1 1 d . . .
C7 C 0.4046(6) 0.30805(8) 1.1457(5) 0.0253(7) Uani 1 1 d . . .
H7A H 0.4221 0.3327 1.1202 0.038 Uiso 1 1 calc R . .
H7B H 0.3707 0.3042 1.2939 0.038 Uiso 1 1 calc R . .
H7C H 0.2576 0.2989 1.0543 0.038 Uiso 1 1 calc R . .
C8 C 0.6537(5) 0.29026(7) 1.0981(5) 0.0207(6) Uani 1 1 d . . .
C9 C 0.7556(6) 0.26252(8) 1.2437(5) 0.0306(7) Uani 1 1 d . . .
H9A H 0.9154 0.2527 1.191 0.046 Uiso 1 1 calc R . .
H9B H 0.6215 0.2446 1.2507 0.046 Uiso 1 1 calc R . .
H9C H 0.7969 0.2721 1.385 0.046 Uiso 1 1 calc R . .
N1 N 0.6979(5) 0.32252(6) 0.8015(4) 0.0197(5) Uani 1 1 d . . .
H1 H 0.525(7) 0.3266(8) 0.776(5) 0.03 Uiso 1 1 d . . .
N2 N 0.4552(5) 0.40737(6) 0.4171(4) 0.0227(5) Uani 1 1 d . . .
N3 N 0.7908(5) 0.29674(6) 0.9407(4) 0.0207(5) Uani 1 1 d . . .
O1 O 1.1054(4) 0.32825(5) 0.6793(3) 0.0284(5) Uani 1 1 d . . .
C10 C 0.0318(6) 0.44828(7) 0.7144(4) 0.0215(6) Uani 1 1 d . . .
C11 C -0.1812(6) 0.47213(8) 0.7800(5) 0.0259(7) Uani 1 1 d . . .
H11A H -0.3492 0.4593 0.7805 0.031 Uiso 1 1 calc R . .
H11B H -0.2058 0.4909 0.6752 0.031 Uiso 1 1 calc R . .
C12 C -0.1163(6) 0.48760(8) 0.9984(5) 0.0251(7) Uani 1 1 d . . .
H12A H -0.0746 0.4689 1.1009 0.03 Uiso 1 1 calc R . .
H12B H -0.273 0.4999 1.0433 0.03 Uiso 1 1 calc R . .
O2 O 0.0716(4) 0.45025(6) 0.5127(3) 0.0299(5) Uani 1 1 d . . .
H2 H 0.205(7) 0.4346(10) 0.482(6) 0.045 Uiso 1 1 d . . .
O3 O 0.1532(5) 0.42889(6) 0.8351(3) 0.0352(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0142(14) 0.0200(14) 0.0197(15) 0.0003(11) -0.0002(11) -0.0028(11)
C2 0.0174(14) 0.0242(15) 0.0148(14) 0.0016(11) -0.0012(11) -0.0019(11)
C3 0.0261(17) 0.0265(16) 0.0242(16) 0.0067(13) -0.0024(13) -0.0029(13)
C4 0.0271(17) 0.0297(16) 0.0200(15) 0.0013(13) 0.0045(13) -0.0050(13)
C5 0.0189(15) 0.0262(15) 0.0245(16) -0.0037(12) 0.0048(12) -0.0016(12)
C6 0.0158(15) 0.0219(14) 0.0176(14) -0.0015(11) -0.0006(11) -0.0006(11)
C7 0.0194(15) 0.0354(17) 0.0214(16) 0.0015(13) 0.0031(12) -0.0008(13)
C8 0.0159(14) 0.0246(15) 0.0209(15) 0.0015(12) -0.0032(12) -0.0044(11)
C9 0.0268(18) 0.0324(18) 0.0326(18) 0.0128(14) 0.0013(14) -0.0019(13)
N1 0.0117(12) 0.0242(13) 0.0231(13) 0.0061(10) 0.0011(10) 0.0023(10)
N2 0.0220(13) 0.0250(13) 0.0207(13) 0.0025(10) -0.0008(10) 0.0012(10)
N3 0.0175(12) 0.0215(12) 0.0229(13) 0.0053(10) -0.0002(10) 0.0020(10)
O1 0.0151(11) 0.0346(12) 0.0357(13) 0.0088(10) 0.0038(9) 0.0035(9)
C10 0.0207(15) 0.0224(15) 0.0209(15) 0.0006(12) -0.0015(12) -0.0026(12)
C11 0.0207(16) 0.0300(16) 0.0267(16) -0.0021(13) -0.0009(13) 0.0016(13)
C12 0.0194(16) 0.0299(16) 0.0262(16) -0.0024(13) 0.0046(12) -0.0011(13)
O2 0.0362(13) 0.0345(12) 0.0189(11) 0.0032(9) 0.0012(10) 0.0148(10)
O3 0.0378(14) 0.0434(14) 0.0248(12) 0.0091(10) 0.0046(10) 0.0152(11)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C1 C5 1.387(4) . ?
C1 C2 1.395(4) . ?
C1 C6 1.489(4) . ?
C2 N2 1.336(4) . ?
C2 H2A 0.95 . ?
C3 N2 1.340(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.95 . ?
C4 C5 1.378(4) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.232(3) . ?
C6 N1 1.359(4) . ?
C7 C8 1.495(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.284(4) . ?
C8 C9 1.491(4) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
N1 N3 1.398(3) . ?
N1 H1 0.90(3) . ?
C10 O3 1.213(3) . ?
C10 O2 1.313(3) . ?
C10 C11 1.510(4) . ?
C11 C12 1.526(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C12 1.528(6) 3_567 ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
O2 H2 0.94(4) . ?

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
C5 C1 C2 117.7(3) . . ?
C5 C1 C6 118.6(3) . . ?
C2 C1 C6 123.7(2) . . ?
N2 C2 C1 122.9(3) . . ?
N2 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
N2 C3 C4 122.5(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C1 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C1 C5 H5 120.1 . . ?
O1 C6 N1 122.9(3) . . ?
O1 C6 C1 121.1(2) . . ?
N1 C6 C1 116.1(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 116.2(3) . . ?
N3 C8 C7 125.6(3) . . ?
C9 C8 C7 118.3(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 N1 N3 117.6(2) . . ?
C6 N1 H1 119(2) . . ?
N3 N1 H1 122(2) . . ?
C2 N2 C3 118.4(3) . . ?
C8 N3 N1 117.1(2) . . ?
O3 C10 O2 123.0(3) . . ?
O3 C10 C11 123.5(3) . . ?
O2 C10 C11 113.4(2) . . ?
C10 C11 C12 112.4(2) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C12 112.3(3) . 3_567 ?
C11 C12 H12A 109.1 . . ?
C12 C12 H12A 109.1 3_567 . ?
C11 C12 H12B 109.1 . . ?
C12 C12 H12B 109.1 3_567 . ?
H12A C12 H12B 107.9 . . ?
C10 O2 H2 109(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 C1 C2 N2 2.3(4) . . . . ?
C6 C1 C2 N2 179.7(3) . . . . ?
N2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C1 1.1(4) . . . . ?
C2 C1 C5 C4 -2.6(4) . . . . ?
C6 C1 C5 C4 179.8(3) . . . . ?
C5 C1 C6 O1 27.1(4) . . . . ?
C2 C1 C6 O1 -150.3(3) . . . . ?
C5 C1 C6 N1 -152.9(3) . . . . ?
C2 C1 C6 N1 29.6(4) . . . . ?
O1 C6 N1 N3 -3.0(4) . . . . ?
C1 C6 N1 N3 177.1(2) . . . . ?
C1 C2 N2 C3 -0.3(4) . . . . ?
C4 C3 N2 C2 -1.4(4) . . . . ?
C9 C8 N3 N1 179.6(2) . . . . ?
C7 C8 N3 N1 -0.3(4) . . . . ?
C6 N1 N3 C8 161.7(3) . . . . ?
O3 C10 C11 C12 38.2(4) . . . . ?
O2 C10 C11 C12 -142.5(3) . . . . ?
C10 C11 C12 C12 67.9(4) . . . 3_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.94(4) 1.73(4) 2.672(3) 177(4) .
C2 H2A O3 0.95 2.66 3.286(4) 124 .
N1 H1 O1 0.90(3) 2.18(3) 3.066(3) 170(3) 1_455
C3 H3 O3 0.95 2.5 3.264(4) 138 1_554
C4 H4 O3 0.95 2.51 3.361(4) 149 1_654
C7 H7C N3 0.98 2.43 3.325(4) 151 1_455
C9 H9B N3 0.98 2.68 3.595(4) 156 4_566
_chemical_name_common            
"(adipic acid).((N'-(propan-2-ylidene)nicotinohydrazide)2"

###END

data_5
_database_code_depnum_ccdc_archive 'CCDC 753785'
#TrackingRef 'Hydrazide_3-7.cif'

_audit_creation_date             2009-11-10T11:24:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(succinic acid).(nicotinic acid hydrazide)2
;
_chemical_formula_moiety         '2(C6 H7 N3 O), C4 H6 O4'
_chemical_formula_sum            'C16 H20 N6 O6'
_chemical_formula_weight         392.38

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0830(4)
_cell_length_b                   26.5860(10)
_cell_length_c                   8.0970(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.449(4)
_cell_angle_gamma                90
_cell_volume                     1684.97(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5830
_cell_measurement_theta_min      3.0158
_cell_measurement_theta_max      28.4311

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3822
_diffrn_measurement_device_type  
'Goniometer Xcalibur, detector: Ruby (Gemini ult'
_diffrn_measurement_method       '\w scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_number            11280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3131
_reflns_number_gt                2530
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/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_number_reflns         3131
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1A C 0.18520(16) 0.50945(5) -0.06719(18) 0.0181(3) Uani 1 1 d . . .
C2A C 0.31773(17) 0.48899(5) 0.04658(19) 0.0211(3) Uani 1 1 d . . .
H2A H 0.3855 0.51 0.132 0.025 Uiso 1 1 calc R . .
C3A C 0.26781(18) 0.41023(5) -0.0715(2) 0.0237(3) Uani 1 1 d . . .
H3A H 0.2976 0.3756 -0.0707 0.028 Uiso 1 1 calc R . .
C4A C 0.13442(18) 0.42734(5) -0.1910(2) 0.0239(3) Uani 1 1 d . . .
H4A H 0.0699 0.4054 -0.2755 0.029 Uiso 1 1 calc R . .
C5A C 0.09267(17) 0.47738(5) -0.18911(19) 0.0215(3) Uani 1 1 d . . .
H5A H -0.0018 0.4901 -0.2735 0.026 Uiso 1 1 calc R . .
C6A C 0.13620(16) 0.56362(5) -0.06482(18) 0.0186(3) Uani 1 1 d . . .
N1A N 0.21972(15) 0.59205(4) 0.06323(17) 0.0219(3) Uani 1 1 d . . .
N2A N 0.35870(14) 0.44045(4) 0.04523(16) 0.0237(3) Uani 1 1 d . . .
N3A N 0.18879(17) 0.64370(4) 0.08004(19) 0.0257(3) Uani 1 1 d . . .
O1A O 0.02330(12) 0.58053(3) -0.17606(14) 0.0247(3) Uani 1 1 d . . .
H1A H 0.298(2) 0.5814(6) 0.145(2) 0.037 Uiso 1 1 d . . .
H3AB H 0.197(2) 0.6606(6) -0.011(3) 0.037 Uiso 1 1 d . . .
H3AA H 0.095(2) 0.6467(6) 0.094(2) 0.037 Uiso 1 1 d . . .
C1B C 1.35946(16) 0.13756(5) 1.01625(19) 0.0185(3) Uani 1 1 d . . .
C2B C 1.24972(17) 0.15837(5) 0.8781(2) 0.0218(3) Uani 1 1 d . . .
H2B H 1.1822 0.1366 0.7951 0.026 Uiso 1 1 calc R . .
C3B C 1.32600(18) 0.23882(5) 0.9659(2) 0.0255(4) Uani 1 1 d . . .
H3B H 1.3125 0.2741 0.9488 0.031 Uiso 1 1 calc R . .
C4B C 1.44059(18) 0.22147(5) 1.1046(2) 0.0259(4) Uani 1 1 d . . .
H4B H 1.5092 0.2442 1.1832 0.031 Uiso 1 1 calc R . .
C5B C 1.45730(17) 0.17016(5) 1.1315(2) 0.0227(3) Uani 1 1 d . . .
H5B H 1.5365 0.1575 1.2298 0.027 Uiso 1 1 calc R . .
C6B C 1.37744(16) 0.08203(5) 1.04590(18) 0.0183(3) Uani 1 1 d . . .
N1B N 1.26519(15) 0.05253(4) 0.94979(16) 0.0206(3) Uani 1 1 d . . .
N2B N 1.23229(15) 0.20794(4) 0.85344(17) 0.0249(3) Uani 1 1 d . . .
N3B N 1.26317(16) -0.00022(4) 0.97003(19) 0.0244(3) Uani 1 1 d . . .
O1B O 1.49125(11) 0.06469(3) 1.15654(13) 0.0233(3) Uani 1 1 d . . .
H1B H 1.184(2) 0.0643(6) 0.876(2) 0.035 Uiso 1 1 d . . .
H3BA H 1.272(2) -0.0070(6) 1.077(2) 0.035 Uiso 1 1 d . . .
H3BB H 1.343(2) -0.0127(6) 0.932(2) 0.035 Uiso 1 1 d . . .
C10 C 0.64784(17) 0.36668(5) 0.2924(2) 0.0207(3) Uani 1 1 d . . .
C11 C 0.78612(18) 0.35376(5) 0.4405(2) 0.0234(3) Uani 1 1 d . . .
H11A H 0.7558 0.3655 0.5452 0.028 Uiso 1 1 calc R . .
H11B H 0.8913 0.3716 0.4324 0.028 Uiso 1 1 calc R . .
C12 C 0.82152(18) 0.29813(5) 0.4546(2) 0.0243(4) Uani 1 1 d . . .
H12A H 0.7183 0.2806 0.47 0.029 Uiso 1 1 calc R . .
H12B H 0.8435 0.2861 0.3463 0.029 Uiso 1 1 calc R . .
C13 C 0.96587(17) 0.28443(5) 0.59437(19) 0.0200(3) Uani 1 1 d . . .
O2 O 0.60710(13) 0.41468(3) 0.29027(14) 0.0260(3) Uani 1 1 d . . .
O3 O 0.58075(14) 0.33699(4) 0.18479(15) 0.0337(3) Uani 1 1 d . . .
O4 O 0.99083(13) 0.23559(3) 0.60417(14) 0.0288(3) Uani 1 1 d . . .
O5 O 1.05048(13) 0.31459(3) 0.68778(15) 0.0291(3) Uani 1 1 d . . .
H2 H 0.517(2) 0.4206(6) 0.196(3) 0.044 Uiso 1 1 d . . .
H4 H 1.084(2) 0.2287(6) 0.698(2) 0.044 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1A 0.0151(7) 0.0195(7) 0.0195(8) 0.0013(6) 0.0042(6) -0.0008(5)
C2A 0.0184(7) 0.0209(7) 0.0215(9) -0.0013(6) 0.0001(6) 0.0007(5)
C3A 0.0239(8) 0.0188(7) 0.0280(9) -0.0011(6) 0.0060(7) 0.0021(5)
C4A 0.0214(7) 0.0220(7) 0.0267(9) -0.0048(6) 0.0029(7) -0.0041(6)
C5A 0.0162(7) 0.0247(8) 0.0222(9) 0.0002(6) 0.0021(6) -0.0014(5)
C6A 0.0137(7) 0.0209(7) 0.0198(8) 0.0020(6) 0.0018(6) -0.0004(5)
N1A 0.0179(6) 0.0174(6) 0.0249(8) -0.0009(5) -0.0051(5) 0.0033(4)
N2A 0.0217(7) 0.0210(6) 0.0258(8) 0.0001(5) 0.0013(6) 0.0037(5)
N3A 0.0231(7) 0.0196(7) 0.0309(8) -0.0027(6) 0.0003(6) 0.0036(5)
O1A 0.0195(5) 0.0225(5) 0.0256(6) 0.0008(4) -0.0067(5) 0.0042(4)
C1B 0.0135(7) 0.0210(7) 0.0210(8) 0.0001(6) 0.0042(6) 0.0011(5)
C2B 0.0183(7) 0.0197(7) 0.0249(9) 0.0001(6) 0.0007(6) 0.0002(5)
C3B 0.0236(8) 0.0174(7) 0.0352(10) 0.0012(6) 0.0065(7) 0.0015(6)
C4B 0.0218(8) 0.0223(8) 0.0321(10) -0.0066(6) 0.0038(7) -0.0035(6)
C5B 0.0169(7) 0.0240(8) 0.0246(9) -0.0021(6) 0.0005(6) 0.0015(5)
C6B 0.0143(7) 0.0229(7) 0.0166(8) 0.0003(6) 0.0017(6) 0.0033(5)
N1B 0.0177(6) 0.0163(6) 0.0231(7) 0.0020(5) -0.0035(5) 0.0019(4)
N2B 0.0207(6) 0.0205(6) 0.0308(8) 0.0045(6) 0.0014(6) 0.0018(5)
N3B 0.0227(7) 0.0172(6) 0.0292(8) 0.0004(6) -0.0011(6) 0.0021(5)
O1B 0.0174(5) 0.0224(5) 0.0249(6) 0.0023(4) -0.0045(4) 0.0038(4)
C10 0.0172(7) 0.0206(7) 0.0236(8) 0.0007(6) 0.0037(6) 0.0002(5)
C11 0.0185(7) 0.0231(8) 0.0257(9) 0.0015(6) 0.0000(6) 0.0020(5)
C12 0.0202(7) 0.0229(8) 0.0268(9) 0.0012(6) 0.0001(6) 0.0029(6)
C13 0.0169(7) 0.0193(7) 0.0237(9) 0.0013(6) 0.0050(6) 0.0004(5)
O2 0.0227(6) 0.0190(5) 0.0300(7) -0.0001(4) -0.0051(5) 0.0060(4)
O3 0.0328(6) 0.0230(6) 0.0356(7) -0.0041(5) -0.0094(5) 0.0035(4)
O4 0.0243(6) 0.0167(5) 0.0376(7) 0.0034(5) -0.0070(5) 0.0030(4)
O5 0.0229(6) 0.0214(5) 0.0369(7) -0.0015(5) -0.0042(5) 0.0021(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C1A C2A 1.341(2) . ?
C1A C5A 1.3757(19) . ?
C1A C6A 1.4951(18) . ?
C2A N2A 1.3329(17) . ?
C2A H2A 0.95 . ?
C3A N2A 1.3160(18) . ?
C3A C4A 1.336(2) . ?
C3A H3A 0.95 . ?
C4A C5A 1.3734(19) . ?
C4A H4A 0.95 . ?
C5A H5A 0.95 . ?
C6A O1A 1.1983(16) . ?
C6A N1A 1.3240(18) . ?
N1A N3A 1.4084(16) . ?
N1A H1A 0.841(19) . ?
N3A H3AB 0.877(19) . ?
N3A H3AA 0.800(19) . ?
C1B C2B 1.360(2) . ?
C1B C5B 1.371(2) . ?
C1B C6B 1.4969(18) . ?
C2B N2B 1.3351(17) . ?
C2B H2B 0.95 . ?
C3B N2B 1.3161(19) . ?
C3B C4B 1.347(2) . ?
C3B H3B 0.95 . ?
C4B C5B 1.383(2) . ?
C4B H4B 0.95 . ?
C5B H5B 0.95 . ?
C6B O1B 1.2042(16) . ?
C6B N1B 1.3005(17) . ?
N1B N3B 1.4127(16) . ?
N1B H1B 0.834(18) . ?
N3B H3BA 0.870(19) . ?
N3B H3BB 0.848(19) . ?
C10 O3 1.2003(17) . ?
C10 O2 1.3170(16) . ?
C10 C11 1.461(2) . ?
C11 C12 1.5054(19) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.455(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 O5 1.1936(17) . ?
C13 O4 1.3132(16) . ?
O2 H2 0.93(2) . ?
O4 H4 0.94(2) . ?

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
C2A C1A C5A 116.07(12) . . ?
C2A C1A C6A 123.40(12) . . ?
C5A C1A C6A 120.53(12) . . ?
N2A C2A C1A 122.98(13) . . ?
N2A C2A H2A 118.5 . . ?
C1A C2A H2A 118.5 . . ?
N2A C3A C4A 121.14(13) . . ?
N2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A C5A 118.54(13) . . ?
C3A C4A H4A 120.7 . . ?
C5A C4A H4A 120.7 . . ?
C4A C5A C1A 121.15(13) . . ?
C4A C5A H5A 119.4 . . ?
C1A C5A H5A 119.4 . . ?
O1A C6A N1A 121.22(12) . . ?
O1A C6A C1A 120.42(12) . . ?
N1A C6A C1A 118.37(12) . . ?
C6A N1A N3A 124.35(12) . . ?
C6A N1A H1A 124.1(11) . . ?
N3A N1A H1A 111.6(11) . . ?
C3A N2A C2A 120.11(12) . . ?
N1A N3A H3AB 111.6(11) . . ?
N1A N3A H3AA 108.0(12) . . ?
H3AB N3A H3AA 109.8(18) . . ?
C2B C1B C5B 116.74(12) . . ?
C2B C1B C6B 123.40(12) . . ?
C5B C1B C6B 119.86(13) . . ?
N2B C2B C1B 123.18(13) . . ?
N2B C2B H2B 118.4 . . ?
C1B C2B H2B 118.4 . . ?
N2B C3B C4B 121.38(13) . . ?
N2B C3B H3B 119.3 . . ?
C4B C3B H3B 119.3 . . ?
C3B C4B C5B 119.29(13) . . ?
C3B C4B H4B 120.4 . . ?
C5B C4B H4B 120.4 . . ?
C1B C5B C4B 119.96(14) . . ?
C1B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
O1B C6B N1B 120.25(12) . . ?
O1B C6B C1B 121.49(12) . . ?
N1B C6B C1B 118.25(12) . . ?
C6B N1B N3B 123.76(12) . . ?
C6B N1B H1B 120.9(11) . . ?
N3B N1B H1B 115.2(11) . . ?
C3B N2B C2B 119.43(13) . . ?
N1B N3B H3BA 108.8(11) . . ?
N1B N3B H3BB 108.4(11) . . ?
H3BA N3B H3BB 113.5(17) . . ?
O3 C10 O2 124.15(13) . . ?
O3 C10 C11 123.75(12) . . ?
O2 C10 C11 112.09(12) . . ?
C10 C11 C12 112.66(12) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 113.93(12) . . ?
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 . . ?
O5 C13 O4 124.81(13) . . ?
O5 C13 C12 123.11(12) . . ?
O4 C13 C12 112.08(12) . . ?
C10 O2 H2 108.7(10) . . ?
C13 O4 H4 108.7(10) . . ?

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
C5A C1A C2A N2A -0.7(2) . . . . ?
C6A C1A C2A N2A 178.82(13) . . . . ?
N2A C3A C4A C5A -0.5(2) . . . . ?
C3A C4A C5A C1A -0.1(2) . . . . ?
C2A C1A C5A C4A 0.7(2) . . . . ?
C6A C1A C5A C4A -178.85(13) . . . . ?
C2A C1A C6A O1A 175.23(14) . . . . ?
C5A C1A C6A O1A -5.3(2) . . . . ?
C2A C1A C6A N1A -5.2(2) . . . . ?
C5A C1A C6A N1A 174.30(13) . . . . ?
O1A C6A N1A N3A -1.5(2) . . . . ?
C1A C6A N1A N3A 178.94(13) . . . . ?
C4A C3A N2A C2A 0.5(2) . . . . ?
C1A C2A N2A C3A 0.1(2) . . . . ?
C5B C1B C2B N2B -1.3(2) . . . . ?
C6B C1B C2B N2B 178.98(13) . . . . ?
N2B C3B C4B C5B -1.5(2) . . . . ?
C2B C1B C5B C4B 0.4(2) . . . . ?
C6B C1B C5B C4B -179.84(13) . . . . ?
C3B C4B C5B C1B 0.9(2) . . . . ?
C2B C1B C6B O1B 169.79(14) . . . . ?
C5B C1B C6B O1B -9.9(2) . . . . ?
C2B C1B C6B N1B -11.0(2) . . . . ?
C5B C1B C6B N1B 169.33(13) . . . . ?
O1B C6B N1B N3B 2.4(2) . . . . ?
C1B C6B N1B N3B -176.88(13) . . . . ?
C4B C3B N2B C2B 0.7(2) . . . . ?
C1B C2B N2B C3B 0.8(2) . . . . ?
O3 C10 C11 C12 -6.7(2) . . . . ?
O2 C10 C11 C12 173.95(13) . . . . ?
C10 C11 C12 C13 176.19(13) . . . . ?
C11 C12 C13 O5 -1.2(2) . . . . ?
C11 C12 C13 O4 178.95(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2A 0.93(2) 1.62(2) 2.540(2) 170(2) .
C3A H3A O3 0.95 2.87 3.446(2) 121 .
O4 H4 N2B 0.94(2) 1.60(2) 2.541(2) 171(2) .
C3B H3B O5 0.95 2.81 3.404(2) 122 .
N1A H1A O1B 0.84(2) 2.08(2) 2.914(2) 172(2) 2_756
N3A H3AB O4 0.88(2) 2.50(2) 3.036(2) 120(1) 2_655
N3A H3AB O3 0.88(2) 2.55(2) 3.213(2) 133(1) 3_665
N3A H3AA O5 0.80(2) 2.57(2) 3.212(2) 139(2) 3_666
N1B H1B O1A 0.83(2) 2.06(2) 2.885(2) 170(2) 2_645
N3B H3BA O2 0.87(2) 2.43(2) 2.995(2) 123(1) 2_746
N3B H3BB O1B 0.85(2) 2.17(2) 2.991(2) 163(2) 3_857
C2A H2A O1B 0.95 2.28 3.219(2) 171 2_756
C2B H2B O1A 0.95 2.26 3.167(2) 159 2_645
_chemical_name_common            '(succinic acid).(nicotinic acid hydrazide)2'

###END

data_6
_database_code_depnum_ccdc_archive 'CCDC 753786'
#TrackingRef 'Hydrazide_3-7.cif'

_audit_creation_date             2009-09-06T15:55:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(sebacic acid).(N'-(propan-2-ylidene)nicotinohydrazide)2
;
_chemical_formula_moiety         'C10 H18 O4, 2(C9 H11 N3 O)'
_chemical_formula_sum            'C28 H40 N6 O6'
_chemical_formula_weight         556.66

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.07070(10)
_cell_length_b                   44.5556(8)
_cell_length_c                   6.39920(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.587(2)
_cell_angle_gamma                90
_cell_volume                     1441.13(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6665
_cell_measurement_theta_min      3.9672
_cell_measurement_theta_max      67.8144

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_special_details           
;
Absorption corrections were made using the program Crysalis
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3822
_diffrn_measurement_device_type  
'Goniometer Xcalibur, detector: Ruby (Gemini ult'
_diffrn_measurement_method       '\w scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_number            10132
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             2595
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET)
(compiled Jan 27 2009,14:17:37)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0837P)^2^+3.0236P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2595
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1912
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 1.2427(5) 0.34831(6) 0.2499(4) 0.0249(6) Uani 1 1 d . . .
C2 C 1.0314(5) 0.36697(6) 0.2852(4) 0.0264(6) Uani 1 1 d . . .
H2A H 0.9516 0.3652 0.414 0.032 Uiso 1 1 calc R . .
C3 C 1.0485(6) 0.38961(7) -0.0356(4) 0.0349(7) Uani 1 1 d . . .
H3 H 0.977 0.4035 -0.1376 0.042 Uiso 1 1 calc R . .
C4 C 1.2648(6) 0.37267(7) -0.0808(4) 0.0348(7) Uani 1 1 d . . .
H4 H 1.3441 0.3753 -0.2091 0.042 Uiso 1 1 calc R . .
C5 C 1.3630(5) 0.35189(6) 0.0644(4) 0.0309(6) Uani 1 1 d . . .
H5 H 1.5125 0.3401 0.0377 0.037 Uiso 1 1 calc R . .
C6 C 1.3526(5) 0.32529(6) 0.4042(4) 0.0255(6) Uani 1 1 d . . .
C7 C 0.8871(5) 0.30061(7) 0.8734(4) 0.0326(6) Uani 1 1 d . . .
H7A H 0.9035 0.3222 0.8484 0.049 Uiso 1 1 calc R . .
H7B H 0.856 0.2972 1.0206 0.049 Uiso 1 1 calc R . .
H7C H 0.7383 0.2926 0.7831 0.049 Uiso 1 1 calc R . .
C8 C 1.1365(5) 0.28518(6) 0.8244(4) 0.0277(6) Uani 1 1 d . . .
C9 C 1.2395(6) 0.26084(7) 0.9698(5) 0.0390(7) Uani 1 1 d . . .
H9A H 1.3948 0.2515 0.9146 0.058 Uiso 1 1 calc R . .
H9B H 1.1019 0.2456 0.9815 0.058 Uiso 1 1 calc R . .
H9C H 1.2895 0.2694 1.1084 0.058 Uiso 1 1 calc R . .
N1 N 1.1792(4) 0.31342(5) 0.5311(4) 0.0262(5) Uani 1 1 d . . .
H1 H 1.014(8) 0.3168(7) 0.505(5) 0.039 Uiso 1 1 d . . .
N2 N 0.9355(5) 0.38731(5) 0.1451(4) 0.0313(6) Uani 1 1 d . . .
N3 N 1.2729(4) 0.29091(5) 0.6696(4) 0.0283(5) Uani 1 1 d . . .
O1 O 1.5872(4) 0.31826(5) 0.4111(3) 0.0345(5) Uani 1 1 d . . .
C10 C 0.5088(7) 0.42425(9) 0.4335(5) 0.0506(9) Uani 1 1 d . . .
C11 C 0.2899(13) 0.44440(17) 0.4933(7) 0.131(3) Uani 1 1 d . . .
H11A H 0.2681 0.4606 0.3875 0.157 Uiso 1 1 calc R . .
H11B H 0.1241 0.4326 0.4831 0.157 Uiso 1 1 calc R . .
C12 C 0.3181(7) 0.45829(7) 0.6994(6) 0.0482(9) Uani 1 1 d . . .
H12A H 0.477 0.4713 0.7059 0.058 Uiso 1 1 calc R . .
H12B H 0.3527 0.4422 0.8045 0.058 Uiso 1 1 calc R . .
C13 C 0.0934(11) 0.47660(14) 0.7640(8) 0.0948(19) Uani 1 1 d . . .
H13A H 0.0565 0.4922 0.6555 0.114 Uiso 1 1 calc R . .
H13B H -0.0637 0.4633 0.7591 0.114 Uiso 1 1 calc R . .
C14 C 0.1113(9) 0.49143(10) 0.9638(8) 0.0711(13) Uani 1 1 d . . .
H14A H 0.2638 0.5053 0.9653 0.085 Uiso 1 1 calc R . .
H14B H 0.1578 0.4759 1.0711 0.085 Uiso 1 1 calc R . .
O2 O 0.5613(5) 0.42669(6) 0.2371(4) 0.0516(7) Uani 1 1 d . . .
H2 H 0.686(10) 0.4138(11) 0.206(7) 0.077 Uiso 1 1 d . . .
O3 O 0.6187(5) 0.40693(6) 0.5548(4) 0.0536(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0177(12) 0.0305(13) 0.0267(13) -0.0017(10) 0.0026(10) -0.0016(10)
C2 0.0211(13) 0.0346(14) 0.0240(13) 0.0015(10) 0.0057(10) 0.0001(10)
C3 0.0376(16) 0.0378(15) 0.0290(14) 0.0074(12) 0.0008(12) -0.0023(12)
C4 0.0360(16) 0.0442(16) 0.0254(14) 0.0004(12) 0.0090(12) -0.0060(12)
C5 0.0234(13) 0.0386(15) 0.0315(14) -0.0055(11) 0.0070(11) -0.0016(11)
C6 0.0199(13) 0.0291(13) 0.0275(13) -0.0034(10) 0.0025(10) 0.0013(10)
C7 0.0219(13) 0.0433(16) 0.0328(15) 0.0019(12) 0.0042(11) -0.0018(11)
C8 0.0206(13) 0.0288(13) 0.0332(14) 0.0006(11) -0.0001(11) -0.0051(10)
C9 0.0322(16) 0.0370(16) 0.0479(18) 0.0131(13) 0.0037(14) -0.0012(12)
N1 0.0166(11) 0.0315(12) 0.0305(12) 0.0044(9) 0.0026(9) 0.0030(8)
N2 0.0280(12) 0.0342(12) 0.0319(12) 0.0045(10) 0.0030(10) 0.0026(9)
N3 0.0215(11) 0.0258(11) 0.0374(13) 0.0049(9) 0.0009(10) 0.0013(8)
O1 0.0170(9) 0.0432(12) 0.0438(12) 0.0077(9) 0.0059(8) 0.0044(8)
C10 0.045(2) 0.070(2) 0.0352(17) -0.0093(16) -0.0029(15) 0.0277(17)
C11 0.127(5) 0.209(7) 0.053(3) -0.037(3) -0.017(3) 0.138(5)
C12 0.051(2) 0.0353(16) 0.063(2) 0.0014(15) 0.0298(17) 0.0067(14)
C13 0.089(4) 0.119(4) 0.077(3) -0.026(3) 0.013(3) 0.066(3)
C14 0.067(3) 0.064(3) 0.086(3) -0.015(2) 0.034(2) 0.019(2)
O2 0.0623(16) 0.0541(15) 0.0382(13) 0.0026(10) 0.0026(11) 0.0317(12)
O3 0.0536(15) 0.0712(16) 0.0376(12) 0.0070(11) 0.0128(11) 0.0275(13)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
C1 C5 1.386(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.500(4) . ?
C2 N2 1.338(3) . ?
C2 H2A 0.95 . ?
C3 N2 1.335(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.95 . ?
C4 C5 1.376(4) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.228(3) . ?
C6 N1 1.351(3) . ?
C7 C8 1.494(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.279(4) . ?
C8 C9 1.496(4) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
N1 N3 1.397(3) . ?
N1 H1 0.86(4) . ?
C10 O3 1.200(4) . ?
C10 O2 1.310(4) . ?
C10 C11 1.501(5) . ?
C11 C12 1.454(6) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.486(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.435(7) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C14 1.469(7) 3_567 ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
O2 H2 0.89(5) . ?

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
C5 C1 C2 117.9(2) . . ?
C5 C1 C6 118.5(2) . . ?
C2 C1 C6 123.6(2) . . ?
N2 C2 C1 122.7(2) . . ?
N2 C2 H2A 118.7 . . ?
C1 C2 H2A 118.7 . . ?
N2 C3 C4 122.8(3) . . ?
N2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C1 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
O1 C6 N1 123.6(2) . . ?
O1 C6 C1 120.4(2) . . ?
N1 C6 C1 116.0(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C7 126.1(2) . . ?
N3 C8 C9 116.3(2) . . ?
C7 C8 C9 117.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 N1 N3 117.2(2) . . ?
C6 N1 H1 119(2) . . ?
N3 N1 H1 122(2) . . ?
C3 N2 C2 118.3(2) . . ?
C8 N3 N1 117.2(2) . . ?
O3 C10 O2 123.7(3) . . ?
O3 C10 C11 122.3(4) . . ?
O2 C10 C11 113.9(3) . . ?
C12 C11 C10 117.7(4) . . ?
C12 C11 H11A 107.9 . . ?
C10 C11 H11A 107.9 . . ?
C12 C11 H11B 107.9 . . ?
C10 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C11 C12 C13 117.7(4) . . ?
C11 C12 H12A 107.9 . . ?
C13 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13A 107.2 . . ?
C12 C13 H13A 107.2 . . ?
C14 C13 H13B 107.2 . . ?
C12 C13 H13B 107.2 . . ?
H13A C13 H13B 106.9 . . ?
C13 C14 C14 121.7(6) . 3_567 ?
C13 C14 H14A 106.9 . . ?
C14 C14 H14A 106.9 3_567 . ?
C13 C14 H14B 106.9 . . ?
C14 C14 H14B 106.9 3_567 . ?
H14A C14 H14B 106.7 . . ?
C10 O2 H2 111(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 C1 C2 N2 2.3(4) . . . . ?
C6 C1 C2 N2 -179.7(2) . . . . ?
N2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C1 0.5(4) . . . . ?
C2 C1 C5 C4 -2.5(4) . . . . ?
C6 C1 C5 C4 179.4(2) . . . . ?
C5 C1 C6 O1 27.5(4) . . . . ?
C2 C1 C6 O1 -150.5(3) . . . . ?
C5 C1 C6 N1 -152.8(2) . . . . ?
C2 C1 C6 N1 29.3(4) . . . . ?
O1 C6 N1 N3 -3.2(4) . . . . ?
C1 C6 N1 N3 177.1(2) . . . . ?
C4 C3 N2 C2 -2.3(4) . . . . ?
C1 C2 N2 C3 0.1(4) . . . . ?
C7 C8 N3 N1 -0.9(4) . . . . ?
C9 C8 N3 N1 179.6(2) . . . . ?
C6 N1 N3 C8 162.2(2) . . . . ?
O3 C10 C11 C12 40.5(9) . . . . ?
O2 C10 C11 C12 -141.6(5) . . . . ?
C10 C11 C12 C13 -176.0(5) . . . . ?
C11 C12 C13 C14 -178.6(6) . . . . ?
C12 C13 C14 C14 -177.2(6) . . . 3_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.89(5) 1.80(5) 2.684(3) 179(5) .
C2 H2A O3 0.95 2.71 3.332(3) 123.5 .
N1 H1 O1 0.86(4) 2.20(4) 3.046(3) 171(3) 1_455
C3 H3 O3 0.95 2.57 3.362(4) 140.5 1_554
C4 H4 O3 0.95 2.56 3.414(4) 150 1_654
C7 H7C N3 0.98 2.41 3.307(3) 151.2 1_455
C9 H9B N3 0.98 2.68 3.610(4) 157.8 4_566
_chemical_name_common            
"(sebacic acid).(N'-(propan-2-ylidene)nicotinohydrazide)2"