#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/33/2233304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233304
loop_
_publ_author_name
'Lemmerer, Andreas'
'Bernstein, Joel'
'Kahlenberg, Volker'
_publ_section_title
;
 Form II of adipic acid--nicotinohydrazide (1/2)
;
_journal_coeditor_code           TK5035
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o190
_journal_paper_doi               10.1107/S1600536811054043
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C6 H7 N3 O, C6 H10 O4'
_chemical_formula_moiety         '2(C6 H7 N3 O), C6 H10 O4'
_chemical_formula_sum            'C18 H24 N6 O6'
_chemical_formula_weight         420.43
_chemical_name_systematic
;
adipic acid--nicotinohydrazide (1/2)
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.729(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.9747(4)
_cell_length_b                   7.3309(2)
_cell_length_c                   8.7451(2)
_cell_measurement_reflns_used    3572
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.453
_cell_measurement_theta_min      3.0659
_cell_volume                     994.87(5)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with a Ruby
(Gemini ultra Mo) detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6207
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.138
_refine_ls_extinction_coef       0.0095(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                1487
_reflns_number_total             1845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5035.cif
_cod_data_source_block           I
_cod_original_cell_volume        994.87(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233304
_cod_database_fobs_code          2233304
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.16016(7) 0.37907(15) 0.35826(13) 0.0237(3) Uani d . 1
C C2 0.22411(7) 0.44813(15) 0.47997(13) 0.0248(3) Uani d . 1
H H2A 0.2294 0.5767 0.4922 0.03 Uiso calc R 1
C C3 0.27134(8) 0.16066(15) 0.56223(15) 0.0296(3) Uani d . 1
H H3 0.3105 0.0841 0.6326 0.036 Uiso calc R 1
C C4 0.20920(8) 0.08110(15) 0.44526(15) 0.0317(3) Uani d . 1
H H4 0.2056 -0.0479 0.4355 0.038 Uiso calc R 1
C C5 0.15231(8) 0.19064(16) 0.34265(14) 0.0291(3) Uani d . 1
H H5 0.1082 0.1384 0.2622 0.035 Uiso calc R 1
C C6 0.09817(8) 0.49832(15) 0.24735(13) 0.0243(3) Uani d . 1
N N1 0.13026(7) 0.65323(12) 0.20370(11) 0.0259(2) Uani d . 1
H H1 0.1859(9) 0.6738(17) 0.2300(15) 0.030(3) Uiso d . 1
N N2 0.27881(6) 0.34156(13) 0.58100(11) 0.0276(3) Uani d . 1
N N3 0.07997(7) 0.77311(15) 0.09121(13) 0.0303(3) Uani d . 1
H H3A 0.0389(9) 0.8250(17) 0.1382(16) 0.036(4) Uiso d . 1
H H3B 0.0508(9) 0.7022(19) 0.0145(18) 0.042(4) Uiso d . 1
O O1 0.02225(5) 0.45309(11) 0.19861(10) 0.0327(2) Uani d . 1
C C7 0.38377(7) 0.67377(15) 0.82289(13) 0.0259(3) Uani d . 1
C C8 0.45756(8) 0.75709(16) 0.94010(16) 0.0352(3) Uani d . 1
H H8A 0.5119 0.7085 0.9206 0.042 Uiso calc R 1
H H8B 0.4543 0.7172 1.0467 0.042 Uiso calc R 1
C C9 0.46178(7) 0.96301(15) 0.93861(14) 0.0281(3) Uani d . 1
H H9A 0.4079 1.0133 0.9588 0.034 Uiso calc R 1
H H9B 0.466 1.0045 0.833 0.034 Uiso calc R 1
O O2 0.39428(6) 0.49783(11) 0.80455(11) 0.0341(2) Uani d . 1
O O3 0.32068(5) 0.75783(10) 0.75195(11) 0.0353(2) Uani d . 1
H H2 0.3478(12) 0.449(2) 0.727(2) 0.069(5) Uiso d . 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C5 . . 118.13(10)
C2 C1 C6 . . 122.68(10)
C5 C1 C6 . . 119.16(10)
N2 C2 C1 . . 122.79(10)
N2 C2 H2A . . 118.6
C1 C2 H2A . . 118.6
N2 C3 C4 . . 122.64(11)
N2 C3 H3 . . 118.7
C4 C3 H3 . . 118.7
C5 C4 C3 . . 119.13(11)
C5 C4 H4 . . 120.4
C3 C4 H4 . . 120.4
C4 C5 C1 . . 119.08(11)
C4 C5 H5 . . 120.5
C1 C5 H5 . . 120.5
O1 C6 N1 . . 122.82(11)
O1 C6 C1 . . 120.92(10)
N1 C6 C1 . . 116.25(10)
C6 N1 N3 . . 122.12(10)
C6 N1 H1 . . 120.3(8)
N3 N1 H1 . . 116.6(8)
C2 N2 C3 . . 118.21(10)
N1 N3 H3A . . 106.8(8)
N1 N3 H3B . . 105.7(9)
H3A N3 H3B . . 105.8(12)
O3 C7 O2 . . 123.24(11)
O3 C7 C8 . . 124.36(10)
O2 C7 C8 . . 112.40(10)
C7 C8 C9 . . 115.55(10)
C7 C8 H8A . . 108.4
C9 C8 H8A . . 108.4
C7 C8 H8B . . 108.4
C9 C8 H8B . . 108.4
H8A C8 H8B . . 107.5
C8 C9 C9 . 3_677 112.33(12)
C8 C9 H9A . . 109.1
C9 C9 H9A 3_677 . 109.1
C8 C9 H9B . . 109.1
C9 C9 H9B 3_677 . 109.1
H9A C9 H9B . . 107.9
C7 O2 H2 . . 110.9(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.3845(16)
C1 C5 . 1.3908(15)
C1 C6 . 1.4932(16)
C2 N2 . 1.3371(15)
C2 H2A . 0.95
C3 N2 . 1.3382(15)
C3 C4 . 1.3747(18)
C3 H3 . 0.95
C4 C5 . 1.3744(17)
C4 H4 . 0.95
C5 H5 . 0.95
C6 O1 . 1.2317(14)
C6 N1 . 1.3383(15)
N1 N3 . 1.4178(14)
N1 H1 . 0.877(14)
N3 H3A . 0.934(14)
N3 H3B . 0.888(15)
C7 O3 . 1.2180(13)
C7 O2 . 1.3154(13)
C7 C8 . 1.4965(17)
C8 C9 . 1.5113(16)
C8 H8A . 0.99
C8 H8B . 0.99
C9 C9 3_677 1.522(2)
C9 H9A . 0.99
C9 H9B . 0.99
O2 H2 . 0.950(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O3 4_575 0.877(14) 2.174(15) 3.0409(14) 169.7(11)
N3 H3A O1 2 0.934(14) 2.129(14) 3.0349(14) 163.0(12)
N3 H3B O1 3_565 0.888(15) 2.258(16) 3.1426(14) 173.7(13)
O2 H2 N2 . 0.950(19) 1.671(19) 2.6126(13) 170.3(16)
C2 H2A O3 . 0.95 2.73 3.3838(14) 126.2
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_site_symmetry_4
_geom_torsion
C5 C1 C2 N2 . 0.84(16)
C6 C1 C2 N2 . 178.88(10)
N2 C3 C4 C5 . 0.17(17)
C3 C4 C5 C1 . 1.15(17)
C2 C1 C5 C4 . -1.61(15)
C6 C1 C5 C4 . -179.73(10)
C2 C1 C6 O1 . -142.57(11)
C5 C1 C6 O1 . 35.46(15)
C2 C1 C6 N1 . 38.30(15)
C5 C1 C6 N1 . -143.68(10)
O1 C6 N1 N3 . -3.28(17)
C1 C6 N1 N3 . 175.83(10)
C1 C2 N2 C3 . 0.45(15)
C4 C3 N2 C2 . -0.97(15)
O3 C7 C8 C9 . -14.84(18)
O2 C7 C8 C9 . 165.28(10)
C7 C8 C9 C9 3_677 179.74(12)
