#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:48:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180356 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/25/7202558.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_7202558
loop_
_publ_author_name
'Christer B. Aakeröy'
'Izhar Hussain'
'Safiyyah Forbes'
'John Desper'
_publ_section_title
;
 Exploring the hydrogen-bond preference of N?H moieties in co-crystals
 assembled via O?H(acid)?N(py) intermolecular interactions
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              46
_journal_paper_doi               10.1039/b614984g
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety
;
(C8 H10 N2 O) (C8 H5 N O6) (H2 O)
;
_chemical_formula_sum            'C16 H17 N3 O8'
_chemical_formula_weight         379.33
_chemical_name_common
'N-(4-pyridylmethyl)acetamide, 5-nitroisophthalic acid hydrate'
_chemical_name_systematic
;
N-(4-pyridylmethyl)acetamide, 5-nitroisophthalic acid hydrate
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.406(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5868(12)
_cell_length_b                   6.8213(5)
_cell_length_c                   14.0335(10)
_cell_measurement_reflns_used    4290
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.65
_cell_measurement_theta_min      2.25
_cell_volume                     1730.8(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21273
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            amber
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2112
_reflns_number_gt                2360
_reflns_number_total             4088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b614984g.txt
_cod_data_source_block           6
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7202558
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
O1A O 0.42073(14) -0.0022(4) 0.4079(2) 0.0658(8) Uani 0.50 1 d PD A 1
H1A H 0.475(3) 0.025(13) 0.458(6) 0.079 Uiso 0.50 1 d PD B 1
H1B H 0.429(4) -0.134(8) 0.364(5) 0.079 Uiso 0.50 1 d PD C 1
O1B O 0.42073(14) -0.0022(4) 0.4079(2) 0.0658(8) Uani 0.50 1 d PD D 2
H1C H 0.406(4) 0.036(12) 0.330(3) 0.079 Uiso 0.50 1 d PD E 2
H1D H 0.480(2) -0.006(15) 0.438(5) 0.079 Uiso 0.50 1 d PD F 2
N11 N 0.24952(13) 0.0096(4) 0.56018(16) 0.0342(6) Uani 1 1 d . . .
H11 H 0.2167(16) 0.016(4) 0.485(2) 0.041 Uiso 1 1 d . . .
C12 C 0.31882(17) 0.0730(4) 0.5803(2) 0.0378(7) Uani 1 1 d . . .
H12 H 0.3403 0.1146 0.5285 0.045 Uiso 1 1 calc R . .
C13 C 0.36005(15) 0.0790(4) 0.67583(19) 0.0330(6) Uani 1 1 d . . .
H13 H 0.4095 0.1257 0.6902 0.040 Uiso 1 1 calc R . .
C14 C 0.32808(14) 0.0159(4) 0.75024(18) 0.0269(6) Uani 1 1 d . . .
C15 C 0.25602(14) -0.0516(4) 0.7263(2) 0.0306(6) Uani 1 1 d . . .
H15 H 0.2335 -0.0981 0.7762 0.037 Uiso 1 1 calc R . .
C16 C 0.21710(15) -0.0515(4) 0.6305(2) 0.0337(7) Uani 1 1 d . . .
H16 H 0.1672 -0.0947 0.6141 0.040 Uiso 1 1 calc R . .
C17 C 0.36851(14) 0.0217(4) 0.85650(19) 0.0323(6) Uani 1 1 d . . .
H17A H 0.3395 0.1021 0.8928 0.039 Uiso 1 1 calc R . .
H17B H 0.3708 -0.1132 0.8832 0.039 Uiso 1 1 calc R . .
N17 N 0.44251(13) 0.0992(4) 0.87467(16) 0.0341(6) Uani 1 1 d . . .
H17 H 0.4498(16) 0.225(5) 0.887(2) 0.041 Uiso 1 1 d . . .
C18 C 0.50041(15) -0.0088(4) 0.8665(2) 0.0339(7) Uani 1 1 d . . .
O18 O 0.49421(11) -0.1835(3) 0.84541(16) 0.0444(6) Uani 1 1 d . . .
C19 C 0.57259(16) 0.0948(5) 0.8818(2) 0.0458(8) Uani 1 1 d . . .
H19A H 0.5679 0.2262 0.9079 0.069 Uiso 1 1 calc R . .
H19B H 0.5871 0.1057 0.8192 0.069 Uiso 1 1 calc R . .
H19C H 0.6103 0.0208 0.9283 0.069 Uiso 1 1 calc R . .
C21 C 0.16033(14) 0.1038(4) 0.21147(18) 0.0255(6) Uani 1 1 d . . .
C27 C 0.20538(14) 0.0652(4) 0.31339(19) 0.0287(6) Uani 1 1 d . . .
O21 O 0.27270(11) 0.0482(3) 0.32727(15) 0.0464(6) Uani 1 1 d . . .
O22 O 0.16942(10) 0.0540(3) 0.38026(13) 0.0354(5) Uani 1 1 d . . .
C22 C 0.09227(13) 0.1949(4) 0.19435(17) 0.0270(6) Uani 1 1 d . . .
H22 H 0.0732 0.2361 0.2483 0.032 Uiso 1 1 calc R . .
C23 C 0.05109(13) 0.2276(4) 0.09981(17) 0.0256(6) Uani 1 1 d . . .
C28 C -0.02113(14) 0.3279(4) 0.07984(18) 0.0286(6) Uani 1 1 d . . .
O23 O -0.03611(11) 0.4104(3) 0.15759(14) 0.0394(5) Uani 1 1 d . . .
H23 H -0.0791(19) 0.468(5) 0.150(3) 0.047 Uiso 1 1 d . . .
O24 O -0.06280(10) 0.3319(3) -0.00060(13) 0.0346(5) Uani 1 1 d . . .
C24 C 0.07765(13) 0.1617(4) 0.02047(17) 0.0275(6) Uani 1 1 d . . .
H24 H 0.0495 0.1787 -0.0447 0.033 Uiso 1 1 calc R . .
C25 C 0.14529(14) 0.0718(4) 0.03870(18) 0.0276(6) Uani 1 1 d . . .
N25 N 0.17360(13) -0.0013(4) -0.04348(16) 0.0353(6) Uani 1 1 d . . .
O25 O 0.13033(12) -0.0099(3) -0.12399(14) 0.0439(6) Uani 1 1 d . . .
O26 O 0.23785(12) -0.0526(4) -0.02829(16) 0.0558(7) Uani 1 1 d . . .
C26 C 0.18852(14) 0.0456(4) 0.13253(19) 0.0271(6) Uani 1 1 d . . .
H26 H 0.2364 -0.0110 0.1426 0.032 Uiso 1 1 calc R . .
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'
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
H1A O1A H1B 106(2) . . ?
H1A O1A H1C 125(8) . . ?
H1B O1A H1C 71(5) . . ?
H1A O1A H1D 20(6) . . ?
H1B O1A H1D 87(6) . . ?
H1C O1A H1D 113(3) . . ?
C12 N11 C16 121.8(2) . . ?
C12 N11 H11 119.4(16) . . ?
C16 N11 H11 118.7(16) . . ?
N11 C12 C13 120.6(3) . . ?
N11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 C17 118.8(2) . . ?
C13 C14 C17 122.4(2) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N11 C16 C15 119.9(3) . . ?
N11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N17 C17 C14 114.9(2) . . ?
N17 C17 H17A 108.5 . . ?
C14 C17 H17A 108.5 . . ?
N17 C17 H17B 108.5 . . ?
C14 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C18 N17 C17 122.7(3) . . ?
C18 N17 H17 118(2) . . ?
C17 N17 H17 119.4(19) . . ?
O18 C18 N17 121.7(3) . . ?
O18 C18 C19 121.8(3) . . ?
N17 C18 C19 116.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 119.4(2) . . ?
C22 C21 C27 122.0(2) . . ?
C26 C21 C27 118.6(2) . . ?
O21 C27 O22 124.6(2) . . ?
O21 C27 C21 119.4(2) . . ?
O22 C27 C21 116.1(2) . . ?
C21 C22 C23 121.3(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 119.6(2) . . ?
C22 C23 C28 122.2(2) . . ?
C24 C23 C28 118.3(2) . . ?
O24 C28 O23 123.4(2) . . ?
O24 C28 C23 123.0(2) . . ?
O23 C28 C23 113.6(2) . . ?
C28 O23 H23 117(2) . . ?
C25 C24 C23 118.4(2) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 122.7(2) . . ?
C24 C25 N25 119.2(2) . . ?
C26 C25 N25 118.0(2) . . ?
O26 N25 O25 123.7(2) . . ?
O26 N25 C25 118.6(2) . . ?
O25 N25 C25 117.6(2) . . ?
C25 C26 C21 118.6(2) . . ?
C25 C26 H26 120.7 . . ?
C21 C26 H26 120.7 . . ?
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
O1A H1A 1.11(3) . ?
O1A H1B 1.12(4) . ?
O1A H1C 1.09(4) . ?
O1A H1D 1.08(4) . ?
N11 C12 1.326(4) . ?
N11 C16 1.336(4) . ?
N11 H11 1.09(3) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 C17 1.507(3) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N17 1.440(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N17 C18 1.331(4) . ?
N17 H17 0.88(3) . ?
C18 O18 1.227(3) . ?
C18 C19 1.487(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.380(4) . ?
C21 C26 1.389(4) . ?
C21 C27 1.504(3) . ?
C27 O21 1.226(3) . ?
C27 O22 1.274(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(3) . ?
C23 C28 1.474(4) . ?
C28 O24 1.212(3) . ?
C28 O23 1.314(3) . ?
O23 H23 0.87(3) . ?
C24 C25 1.368(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(4) . ?
C25 N25 1.462(3) . ?
N25 O26 1.215(3) . ?
N25 O25 1.227(3) . ?
C26 H26 0.9500 . ?
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
O1A H1A O1A 1.11(3) 2.37(4) 3.440(6) 162(8) 3_656
O1A H1B O18 1.12(4) 1.80(5) 2.790(3) 145(5) 4
O1B H1C O21 1.09(4) 2.48(7) 2.743(3) 92(4) .
O1B H1D O18 1.08(4) 2.53(9) 2.790(3) 92(5) 4
N11 H11 O22 1.09(3) 1.55(3) 2.635(3) 173(3) .
N17 H17 O1A 0.88(3) 2.01(3) 2.833(4) 156(3) 4_566
O23 H23 O22 0.87(3) 1.74(3) 2.602(3) 171(3) 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
C16 N11 C12 C13 -0.4(4) . . . . ?
N11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 C17 -178.6(3) . . . . ?
C13 C14 C15 C16 -1.3(4) . . . . ?
C17 C14 C15 C16 177.6(2) . . . . ?
C12 N11 C16 C15 -0.8(4) . . . . ?
C14 C15 C16 N11 1.6(4) . . . . ?
C15 C14 C17 N17 -178.3(2) . . . . ?
C13 C14 C17 N17 0.5(4) . . . . ?
C14 C17 N17 C18 -82.5(3) . . . . ?
C17 N17 C18 O18 -2.1(4) . . . . ?
C17 N17 C18 C19 176.5(2) . . . . ?
C22 C21 C27 O21 -155.2(3) . . . . ?
C26 C21 C27 O21 24.8(4) . . . . ?
C22 C21 C27 O22 24.2(4) . . . . ?
C26 C21 C27 O22 -155.8(2) . . . . ?
C26 C21 C22 C23 0.7(4) . . . . ?
C27 C21 C22 C23 -179.3(2) . . . . ?
C21 C22 C23 C24 2.1(4) . . . . ?
C21 C22 C23 C28 -178.9(2) . . . . ?
C22 C23 C28 O24 -168.6(2) . . . . ?
C24 C23 C28 O24 10.5(4) . . . . ?
C22 C23 C28 O23 10.8(4) . . . . ?
C24 C23 C28 O23 -170.2(2) . . . . ?
C22 C23 C24 C25 -2.1(4) . . . . ?
C28 C23 C24 C25 178.8(2) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C23 C24 C25 N25 179.0(2) . . . . ?
C24 C25 N25 O26 168.6(3) . . . . ?
C26 C25 N25 O26 -11.8(4) . . . . ?
C24 C25 N25 O25 -12.4(4) . . . . ?
C26 C25 N25 O25 167.2(2) . . . . ?
C24 C25 C26 C21 3.4(4) . . . . ?
N25 C25 C26 C21 -176.2(2) . . . . ?
C22 C21 C26 C25 -3.4(4) . . . . ?
C27 C21 C26 C25 176.6(2) . . . . ?
