#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:46:26 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228933 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/96/7229685.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_7229685
loop_
_publ_author_name
'Lombard, Jean'
'Loots, Leigh'
'le Roex, Tanya'
'Haynes, Delia A.'
_publ_section_title
;
 Formation of multi-component crystals with a series of
 pyridinium-carboxyacrylate zwitterions
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              25
_journal_paper_doi               10.1039/C7CE01953J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C6 H7 N2 O, 0.5(C4 O4)'
_chemical_formula_sum            'C8 H7 N2 O3'
_chemical_formula_weight         179.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                95.723(8)
_cell_angle_beta                 93.218(8)
_cell_angle_gamma                97.153(8)
_cell_formula_units_Z            2
_cell_length_a                   3.671(3)
_cell_length_b                   7.594(5)
_cell_length_c                   13.772(10)
_cell_measurement_reflns_used    1886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.96
_cell_volume                     378.1(5)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_molecular_graphics
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4363
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.592
_diffrn_reflns_theta_min         1.490
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             186
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0424
_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)+(0.0649P)²+0.0470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1466
_reflns_number_total             1758
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01953j2.cif
_cod_data_source_block           Salt2a
_cod_depositor_comments
'Adding full bibliography for 7229684--7229689.cif.'
_cod_database_code               7229685
_shelx_shelxl_version_number     2016/6
_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   0.978
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.5150(3) 0.51222(15) 0.19648(8) 0.0142(3) Uani 1 1 d . .
C2 C 0.5395(4) 0.56960(18) 0.29219(10) 0.0148(3) Uani 1 1 d . .
H2 H 0.481475 0.685179 0.313237 0.018 Uiso 1 1 calc R U
C3 C 0.6488(4) 0.46151(17) 0.36039(10) 0.0142(3) Uani 1 1 d . .
H3 H 0.669042 0.502670 0.428157 0.017 Uiso 1 1 calc R U
C4 C 0.7289(3) 0.29141(17) 0.32860(9) 0.0125(3) Uani 1 1 d . .
C5 C 0.7037(4) 0.23616(17) 0.22902(10) 0.0136(3) Uani 1 1 d . .
H5 H 0.759977 0.121306 0.205782 0.016 Uiso 1 1 calc R U
C6 C 0.5953(4) 0.35066(17) 0.16397(10) 0.0149(3) Uani 1 1 d . .
H6 H 0.577873 0.314094 0.095673 0.018 Uiso 1 1 calc R U
C7 C 0.8368(3) 0.17370(17) 0.40536(10) 0.0134(3) Uani 1 1 d . .
O8 O 0.8115(3) 0.22324(13) 0.49263(7) 0.0185(3) Uani 1 1 d . .
N9 N 0.9564(3) 0.02136(15) 0.37304(8) 0.0162(3) Uani 1 1 d . .
H9A H 1.023285 -0.050968 0.414852 0.019 Uiso 1 1 calc R U
H9B H 0.968485 -0.006941 0.309866 0.019 Uiso 1 1 calc R U
O10 O 0.1058(3) 0.86774(13) 0.18716(7) 0.0194(3) Uani 1 1 d . .
O11 O 0.2944(3) 0.69612(12) 0.06379(7) 0.0179(3) Uani 1 1 d . .
C12 C 0.1542(4) 0.83030(17) 0.09970(10) 0.0131(3) Uani 1 1 d . .
C13 C 0.0440(4) 0.95012(17) 0.02844(10) 0.0149(3) Uani 1 1 d . .
H1 H 0.415(6) 0.592(3) 0.1449(17) 0.056(6) 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 0.0000 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
C6 N1 C2 121.60(11) .
C6 N1 H1 118.3(13) .
C2 N1 H1 120.0(13) .
N1 C2 C3 120.36(13) .
N1 C2 H2 119.8 .
C3 C2 H2 119.8 .
C2 C3 C4 119.24(13) .
C2 C3 H3 120.4 .
C4 C3 H3 120.4 .
C5 C4 C3 119.10(11) .
C5 C4 C7 122.87(12) .
C3 C4 C7 118.03(13) .
C6 C5 C4 119.14(13) .
C6 C5 H5 120.4 .
C4 C5 H5 120.4 .
N1 C6 C5 120.56(13) .
N1 C6 H6 119.7 .
C5 C6 H6 119.7 .
O8 C7 N9 124.06(11) .
O8 C7 C4 119.21(12) .
N9 C7 C4 116.73(13) .
C7 N9 H9A 120.0 .
C7 N9 H9B 120.0 .
H9A N9 H9B 120.0 .
O10 C12 O11 125.96(11) .
O10 C12 C13 118.82(12) .
O11 C12 C13 115.22(13) .
C13 C13 C12 179.0(2) 2_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.3371(19) .
N1 C2 1.341(2) .
N1 H1 1.06(2) .
C2 C3 1.3821(18) .
C2 H2 0.9500 .
C3 C4 1.394(2) .
C3 H3 0.9500 .
C4 C5 1.388(2) .
C4 C7 1.5175(18) .
C5 C6 1.3850(18) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 O8 1.2352(19) .
C7 N9 1.3322(18) .
N9 H9A 0.8800 .
N9 H9B 0.8800 .
O10 C12 1.2376(18) .
O11 C12 1.2673(17) .
C12 C13 1.4765(18) .
C13 C13 1.201(3) 2_575
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
N1 H1 O11 1.06(2) 1.51(2) 2.5631(18) 174(2) .
N9 H9A O8 0.88 2.04 2.9156(19) 177.7 2_756
N9 H9B O10 0.88 1.98 2.817(2) 159.1 1_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
C6 N1 C2 C3 -0.18(19)
N1 C2 C3 C4 -0.8(2)
C2 C3 C4 C5 1.22(19)
C2 C3 C4 C7 -178.16(11)
C3 C4 C5 C6 -0.77(19)
C7 C4 C5 C6 178.58(12)
C2 N1 C6 C5 0.65(19)
C4 C5 C6 N1 -0.2(2)
C5 C4 C7 O8 -171.48(12)
C3 C4 C7 O8 7.87(18)
C5 C4 C7 N9 8.84(19)
C3 C4 C7 N9 -171.80(11)
