#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/53/7205308.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7205308
loop_
_publ_author_name
'Lemmerer, Andreas'
'Bernstein, Joel'
'Kahlenberg, Volker'
_publ_section_title
;
 Covalent assistance to supramolecular synthesis: directing the
 supramolecular assembly of co-crystals by in situ modification of
 hydrogen bonding functionality
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              55
_journal_paper_doi               10.1039/c0ce00347f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         '2(C6 H7 N3 O), C4 H6 O4'
_chemical_formula_sum            'C16 H20 N6 O6'
_chemical_formula_weight         392.38
_chemical_name_common            '(succinic acid).(nicotinic acid hydrazide)2'
_chemical_name_systematic
;
(succinic acid).(nicotinic acid hydrazide)2
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-11-10T11:24:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.449(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0830(4)
_cell_length_b                   26.5860(10)
_cell_length_c                   8.0970(4)
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.4311
_cell_measurement_theta_min      3.0158
_cell_volume                     1684.97(14)
_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_collection
;
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_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.3822
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Goniometer Xcalibur, detector: Ruby (Gemini ult'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.031
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11280
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                2530
_reflns_number_total             3131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00347F.TXT
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1684.97(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205308
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'
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_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_
_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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653727
