#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/94/4509499.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509499
loop_
_publ_author_name
'Mohamed, Sharmarke'
'Tocher, Derek A.'
'Vickers, Martin'
'Karamertzanis, Panagiotis G.'
'Price, Sarah L.'
_publ_section_title
;
 Salt or Cocrystal? A New Series of Crystal Structures Formed from Simple
 Pyridines and Carboxylic Acids
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2881
_journal_paper_doi               10.1021/cg9001994
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         '2(C5 H5 N1), C4 H4 O4'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_name_common            'Pyridine fumaric acid'
_chemical_name_systematic
; 
 Pyridine fumaric acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.436(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8195(6)
_cell_length_b                   10.2834(15)
_cell_length_c                   17.067(3)
_cell_measurement_reflns_used    1712
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.419
_cell_measurement_theta_min      3.963
_cell_volume                     670.14(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;    
SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5581
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0574P)²+0.1190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1309
_reflns_number_total             1594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9001994sup1.cif
_cod_data_source_block           str0603
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        670.15(17)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4509499
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'
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
C1 C 1.8699(3) -0.17639(12) 0.77952(7) 0.0297(3) Uani 1 1 d
C2 C 1.7286(3) -0.21279(13) 0.84975(8) 0.0328(3) Uani 1 1 d
C3 C 1.7154(4) -0.12235(14) 0.90919(8) 0.0347(3) Uani 1 1 d
C4 C 1.8417(4) 0.00147(13) 0.89667(8) 0.0328(3) Uani 1 1 d
C5 C 1.9822(3) 0.02968(12) 0.82483(7) 0.0279(3) Uani 1 1 d
H1 H 1.894(4) -0.2354(15) 0.7354(9) 0.036(4) Uiso 1 1 d
H2 H 1.649(4) -0.2983(16) 0.8566(9) 0.039(4) Uiso 1 1 d
H3 H 1.618(4) -0.1468(14) 0.9594(10) 0.042(4) Uiso 1 1 d
H4 H 1.831(4) 0.0678(15) 0.9359(9) 0.042(4) Uiso 1 1 d
H5 H 2.078(4) 0.1124(14) 0.8151(8) 0.028(3) Uiso 1 1 d
N1 N 1.9957(3) -0.05709(10) 0.76695(5) 0.0265(3) Uani 1 1 d
C6 C 2.3073(3) -0.09484(11) 0.58681(7) 0.0258(3) Uani 1 1 d
H6 H 2.528(4) -0.1317(14) 0.4788(9) 0.034(4) Uiso 1 1 d
C7 C 2.4708(3) -0.06018(11) 0.51141(7) 0.0260(3) Uani 1 1 d
O1 O 2.2078(3) -0.20504(8) 0.59957(5) 0.0384(3) Uani 1 1 d
O2 O 2.2793(3) 0.00265(8) 0.63560(5) 0.0322(3) Uani 1 1 d
H7 H 2.165(6) -0.031(2) 0.6884(13) 0.083(7) 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
C1 0.0304(7) 0.0275(6) 0.0312(7) -0.0018(5) -0.0004(5) -0.0001(5)
C2 0.0299(7) 0.0294(7) 0.0391(7) 0.0090(5) 0.0008(5) -0.0039(5)
C3 0.0299(7) 0.0456(8) 0.0291(7) 0.0100(5) 0.0070(5) 0.0049(6)
C4 0.0353(7) 0.0374(7) 0.0257(6) -0.0034(5) 0.0021(5) 0.0073(5)
C5 0.0305(6) 0.0242(6) 0.0289(6) 0.0019(5) -0.0010(5) 0.0013(5)
N1 0.0279(5) 0.0286(5) 0.0230(5) 0.0016(4) 0.0013(4) 0.0009(4)
C6 0.0301(6) 0.0239(6) 0.0234(6) 0.0030(4) -0.0007(4) 0.0019(5)
C7 0.0319(7) 0.0240(6) 0.0222(6) -0.0013(4) 0.0009(5) 0.0011(5)
O1 0.0582(7) 0.0243(5) 0.0333(5) 0.0035(4) 0.0109(4) -0.0041(4)
O2 0.0466(6) 0.0266(5) 0.0238(5) -0.0003(3) 0.0072(4) -0.0037(4)
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
N1 C1 C2 122.61(12)
N1 C1 H1 114.0(9)
C2 C1 H1 123.4(9)
C3 C2 C1 118.63(12)
C3 C2 H2 121.5(9)
C1 C2 H2 119.9(9)
C2 C3 C4 119.29(12)
C2 C3 H3 119.6(9)
C4 C3 H3 121.1(9)
C3 C4 C5 118.44(12)
C3 C4 H4 121.8(10)
C5 C4 H4 119.7(10)
N1 C5 C4 122.70(12)
N1 C5 H5 116.8(9)
C4 C5 H5 120.5(9)
C5 N1 C1 118.33(10)
O1 C6 O2 124.63(11)
O1 C6 C7 121.19(11)
O2 C6 C7 114.17(10)
C6 C7 H6 115.4(9)
C6 O2 H7 109.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3369(16)
C1 C2 1.3785(18)
C1 H1 0.973(16)
C2 C3 1.378(2)
C2 H2 0.940(16)
C3 C4 1.380(2)
C3 H3 0.975(17)
C4 C5 1.3815(19)
C4 H4 0.957(16)
C5 N1 1.3331(16)
C5 H5 0.943(14)
C6 O1 1.2167(14)
C6 O2 1.3093(14)
C6 C7 1.4878(17)
C7 H6 0.952(15)
O2 H7 1.07(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
O2 H7 N1 1.07(2) 1.53(2) 2.5880(13) 171.3(19)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C1 C2 C3 0.3(2)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 -0.9(2)
C3 C4 C5 N1 1.0(2)
C4 C5 N1 C1 -0.48(18)
C2 C1 N1 C5 -0.19(18)
