#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:46:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180095 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/41/7054157.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_7054157
loop_
_publ_author_name
'Loots, Leigh'
'Haynes, Delia A.'
'Roex, Tanya le'
_publ_section_title
;
 Synthesis and solid-state supramolecular chemistry of a series of
 pyridinium-derived zwitterions
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2778
_journal_paper_doi               10.1039/c4nj00281d
_journal_volume                  38
_journal_year                    2014
_chemical_formula_moiety         'C10 H6 N2 O4'
_chemical_formula_sum            'C10 H6 N2 O4'
_chemical_formula_weight         218.17
_chemical_melting_point          460.15
_chemical_name_common            \4
_chemical_name_systematic
(2Z)-3-carboxy-2-(4-cyanopyridinium-1-yl)-1-hydroxyprop-2-en-1-olate
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 112.227(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.097(3)
_cell_length_b                   19.995(8)
_cell_length_c                   7.478(3)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      3.101
_cell_volume                     982.3(7)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics
'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX CCD area -detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6115
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.953
_diffrn_reflns_theta_min         2.037
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, 2012'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       shard
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0540P)²+0.2489P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1788
_reflns_number_total             2232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4nj00281d2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7054154--7054163.cif.'
_cod_database_code               7054157
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.33747(15) 0.43334(5) 0.24036(14) 0.0218(3) Uani 1 1 d . .
N1 N 0.59630(17) 0.37600(6) 0.73111(16) 0.0176(3) Uani 1 1 d . .
C1 C 0.4694(2) 0.40313(7) 0.3813(2) 0.0189(3) Uani 1 1 d . .
O2 O 0.61819(18) 0.37130(6) 0.38316(16) 0.0313(3) Uani 1 1 d . .
N2 N 1.1799(2) 0.26250(8) 1.3238(2) 0.0384(4) Uani 1 1 d . .
C2 C 0.4363(2) 0.40863(7) 0.57045(19) 0.0185(3) Uani 1 1 d . .
O3 O 0.10356(17) 0.47988(6) 0.78076(16) 0.0300(3) Uani 1 1 d . .
C3 C 0.2833(2) 0.44009(8) 0.5940(2) 0.0223(3) Uani 1 1 d . .
H3 H 0.186(3) 0.4622(8) 0.485(3) 0.023(4) Uiso 1 1 d . .
H4 H 0.361(4) 0.4250(12) 1.048(4) 0.062(7) Uiso 1 1 d . .
O4 O 0.37890(19) 0.41701(7) 0.92568(16) 0.0382(3) Uani 1 1 d . .
C4 C 0.2465(2) 0.44775(8) 0.7782(2) 0.0226(3) Uani 1 1 d . .
C5 C 0.5881(2) 0.30944(7) 0.7538(2) 0.0217(3) Uani 1 1 d . .
H5 H 0.4793 0.2842 0.6652 0.026 Uiso 1 1 calc R U
C6 C 0.7366(2) 0.27796(8) 0.9048(2) 0.0237(3) Uani 1 1 d . .
H6 H 0.7327 0.2310 0.9219 0.028 Uiso 1 1 calc R U
C7 C 0.8932(2) 0.31654(8) 1.0324(2) 0.0211(3) Uani 1 1 d . .
C8 C 0.8990(2) 0.38470(8) 1.0064(2) 0.0228(3) Uani 1 1 d . .
H8 H 1.0058 0.4110 1.0935 0.027 Uiso 1 1 calc R U
C9 C 0.7470(2) 0.41377(8) 0.8517(2) 0.0211(3) Uani 1 1 d . .
H9 H 0.7489 0.4606 0.8305 0.025 Uiso 1 1 calc R U
C10 C 1.0534(2) 0.28567(8) 1.1943(2) 0.0272(4) Uani 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 0.0000 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
C9 N1 C5 122.26(12)
C9 N1 C2 118.47(12)
C5 N1 C2 119.27(11)
O2 C1 O1 128.15(13)
O2 C1 C2 117.46(12)
O1 C1 C2 114.39(12)
C3 C2 N1 121.73(13)
C3 C2 C1 125.50(13)
N1 C2 C1 112.76(12)
C2 C3 C4 127.30(14)
C2 C3 H3 118.4(10)
C4 C3 H3 114.3(10)
C4 O4 H4 114.0(14)
O3 C4 O4 125.46(14)
O3 C4 C3 120.46(13)
O4 C4 C3 114.09(13)
N1 C5 C6 120.07(13)
N1 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C7 118.39(14)
C5 C6 H6 120.8
C7 C6 H6 120.8
C8 C7 C6 120.64(13)
C8 C7 C10 118.88(13)
C6 C7 C10 120.48(14)
C9 C8 C7 118.68(14)
C9 C8 H8 120.7
C7 C8 H8 120.7
N1 C9 C8 119.96(14)
N1 C9 H9 120.0
C8 C9 H9 120.0
N2 C10 C7 178.65(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2672(17)
N1 C9 1.3410(19)
N1 C5 1.346(2)
N1 C2 1.4583(17)
C1 O2 1.2285(18)
C1 C2 1.523(2)
N2 C10 1.141(2)
C2 C3 1.323(2)
O3 C4 1.2068(18)
C3 C4 1.504(2)
C3 H3 0.954(18)
O4 C4 1.3010(18)
O4 H4 0.98(3)
C5 C6 1.372(2)
C5 H5 0.9500
C6 C7 1.392(2)
C6 H6 0.9500
C7 C8 1.379(2)
C7 C10 1.448(2)
C8 C9 1.377(2)
C8 H8 0.9500
C9 H9 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
C3 H3 O3 0.954(18) 2.534(18) 3.483(2) 172.8(14) 3_566
O4 H4 O1 0.98(3) 1.52(3) 2.5008(17) 177(2) 1_556
C6 H6 O2 0.95 2.18 3.088(2) 159.8 4_566
C8 H8 O1 0.95 2.23 3.094(2) 150.1 1_656
C9 H9 O1 0.95 2.22 3.141(2) 164.3 3_666
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
C9 N1 C2 C3 -80.61(18)
C5 N1 C2 C3 99.26(17)
C9 N1 C2 C1 98.28(15)
C5 N1 C2 C1 -81.85(16)
O2 C1 C2 C3 -179.07(15)
O1 C1 C2 C3 1.6(2)
O2 C1 C2 N1 2.10(18)
O1 C1 C2 N1 -177.24(11)
N1 C2 C3 C4 -0.2(2)
C1 C2 C3 C4 -178.89(14)
C2 C3 C4 O3 177.45(16)
C2 C3 C4 O4 -2.9(2)
C9 N1 C5 C6 0.3(2)
C2 N1 C5 C6 -179.59(13)
N1 C5 C6 C7 0.3(2)
C5 C6 C7 C8 -0.4(2)
C5 C6 C7 C10 179.89(14)
C6 C7 C8 C9 -0.1(2)
C10 C7 C8 C9 179.65(14)
C5 N1 C9 C8 -0.8(2)
C2 N1 C9 C8 179.11(13)
C7 C8 C9 N1 0.6(2)
