#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:36:05 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516503.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_4516503
loop_
_publ_author_name
'Loots, Leigh'
'O’Connor, James P.'
'le Roex, Tanya'
'Haynes, Delia A.'
_publ_section_title
;
 Solid-State Supramolecular Chemistry of a Benzylpyridine-Functionalized
 Zwitterion: Polymorphism, Interconversion, and Porosity
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5849
_journal_paper_doi               10.1021/acs.cgd.5b01238
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27
_chemical_name_systematic
(2Z)-2-(4-benzylpyridinium-1-yl-3-carboxy-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'
_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                 92.374(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.197(3)
_cell_length_b                   6.208(2)
_cell_length_c                   26.752(9)
_cell_measurement_reflns_used    1899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7155
_cell_measurement_theta_min      2.487
_cell_volume                     1360.2(8)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.902
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8231
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         1.524
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2012'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       shard
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.049
_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     194
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0420P)²+0.1134P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             3102
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01238_si_002.cif
_cod_data_source_block           III
_cod_original_cell_volume        1360.1(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516503
_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   0.982
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2012-9
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
O3 O 0.38247(12) 0.31029(18) 0.39510(4) 0.0219(3) Uani 1 1 d . .
O1 O 0.29234(13) -0.19787(17) 0.49914(4) 0.0237(3) Uani 1 1 d . .
N1 N 0.19810(14) 0.30873(19) 0.55805(4) 0.0145(3) Uani 1 1 d . .
O4 O 0.40199(14) -0.01974(18) 0.42655(4) 0.0243(3) Uani 1 1 d . .
O2 O 0.10782(14) -0.10965(18) 0.55475(4) 0.0299(3) Uani 1 1 d . .
C2 C 0.24855(17) 0.1733(2) 0.51682(5) 0.0145(3) Uani 1 1 d . .
C11 C 0.16410(18) 0.7459(3) 0.71978(5) 0.0183(3) Uani 1 1 d . .
C9 C 0.31218(17) 0.4110(2) 0.58704(5) 0.0164(3) Uani 1 1 d . .
H9 H 0.4245 0.3944 0.5804 0.020 Uiso 1 1 calc R U
C4 C 0.36844(17) 0.1857(2) 0.42979(6) 0.0181(3) Uani 1 1 d . .
C12 C 0.18431(19) 0.5785(3) 0.75403(6) 0.0211(4) Uani 1 1 d . .
H12 H 0.1286 0.4462 0.7481 0.025 Uiso 1 1 calc R U
C5 C 0.03745(18) 0.3286(2) 0.56715(6) 0.0188(3) Uani 1 1 d . .
H5 H -0.0418 0.2557 0.5465 0.023 Uiso 1 1 calc R U
C8 C 0.26753(18) 0.5380(2) 0.62580(5) 0.0177(3) Uani 1 1 d . .
H8 H 0.3489 0.6090 0.6460 0.021 Uiso 1 1 calc R U
C3 C 0.31105(17) 0.2744(2) 0.47832(5) 0.0156(3) Uani 1 1 d . .
H3 H 0.3211 0.4261 0.4820 0.019 Uiso 1 1 calc R U
C6 C -0.01114(18) 0.4530(3) 0.60594(6) 0.0193(3) Uani 1 1 d . .
H6 H -0.1238 0.4635 0.6125 0.023 Uiso 1 1 calc R U
C1 C 0.21171(19) -0.0642(2) 0.52495(6) 0.0198(3) Uani 1 1 d . .
C15 C 0.3511(2) 0.9601(3) 0.77122(7) 0.0302(4) Uani 1 1 d . .
H15 H 0.4093 1.0907 0.7769 0.036 Uiso 1 1 calc R U
C10 C 0.04844(19) 0.7196(3) 0.67492(5) 0.0225(4) Uani 1 1 d . .
H10A H -0.0584 0.6706 0.6866 0.027 Uiso 1 1 calc R U
H10B H 0.0315 0.8624 0.6591 0.027 Uiso 1 1 calc R U
C13 C 0.28442(19) 0.6019(3) 0.79668(6) 0.0248(4) Uani 1 1 d . .
H13 H 0.2968 0.4865 0.8199 0.030 Uiso 1 1 calc R U
C16 C 0.2505(2) 0.9362(3) 0.72856(6) 0.0261(4) Uani 1 1 d . .
H16 H 0.2405 1.0508 0.7051 0.031 Uiso 1 1 calc R U
C7 C 0.10327(18) 0.5643(2) 0.63583(5) 0.0177(3) Uani 1 1 d . .
C14 C 0.3664(2) 0.7940(3) 0.80540(6) 0.0276(4) Uani 1 1 d . .
H14 H 0.4334 0.8116 0.8350 0.033 Uiso 1 1 calc R U
H4 H 0.363(3) -0.097(4) 0.4596(9) 0.070(7) 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
C1 O1 H4 111.2(9)
C9 N1 C5 120.65(13)
C9 N1 C2 119.61(12)
C5 N1 C2 119.74(12)
C4 O4 H4 108.2(12)
C3 C2 N1 116.38(13)
C3 C2 C1 130.87(13)
N1 C2 C1 112.68(12)
C12 C11 C16 118.48(15)
C12 C11 C10 119.85(14)
C16 C11 C10 121.66(15)
N1 C9 C8 120.50(14)
N1 C9 H9 119.8
C8 C9 H9 119.8
O3 C4 O4 122.84(14)
O3 C4 C3 117.92(14)
O4 C4 C3 119.24(14)
C13 C12 C11 120.99(15)
C13 C12 H12 119.5
C11 C12 H12 119.5
N1 C5 C6 120.28(14)
N1 C5 H5 119.9
C6 C5 H5 119.9
C9 C8 C7 120.38(14)
C9 C8 H8 119.8
C7 C8 H8 119.8
C2 C3 C4 129.90(14)
C2 C3 H3 115.0
C4 C3 H3 115.0
C5 C6 C7 120.46(14)
C5 C6 H6 119.8
C7 C6 H6 119.8
O2 C1 O1 126.18(15)
O2 C1 C2 117.66(14)
O1 C1 C2 116.15(13)
C14 C15 C16 119.96(16)
C14 C15 H15 120.0
C16 C15 H15 120.0
C7 C10 C11 115.24(13)
C7 C10 H10A 108.5
C11 C10 H10A 108.5
C7 C10 H10B 108.5
C11 C10 H10B 108.5
H10A C10 H10B 107.5
C14 C13 C12 119.74(16)
C14 C13 H13 120.1
C12 C13 H13 120.1
C15 C16 C11 120.68(16)
C15 C16 H16 119.7
C11 C16 H16 119.7
C6 C7 C8 117.70(14)
C6 C7 C10 120.29(13)
C8 C7 C10 121.86(14)
C15 C14 C13 120.11(16)
C15 C14 H14 119.9
C13 C14 H14 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C4 1.2175(18)
O1 C1 1.2807(19)
O1 H4 1.38(2)
N1 C9 1.3486(18)
N1 C5 1.3546(18)
N1 C2 1.4603(18)
O4 C4 1.3081(19)
O4 H4 1.07(2)
O2 C1 1.2234(19)
C2 C3 1.327(2)
C2 C1 1.522(2)
C11 C12 1.391(2)
C11 C16 1.392(2)
C11 C10 1.507(2)
C9 C8 1.365(2)
C9 H9 0.9500
C4 C3 1.504(2)
C12 C13 1.385(2)
C12 H12 0.9500
C5 C6 1.366(2)
C5 H5 0.9500
C8 C7 1.393(2)
C8 H8 0.9500
C3 H3 0.9500
C6 C7 1.391(2)
C6 H6 0.9500
C15 C14 1.381(2)
C15 C16 1.388(2)
C15 H15 0.9500
C10 C7 1.505(2)
C10 H10A 0.9900
C10 H10B 0.9900
C13 C14 1.384(2)
C13 H13 0.9500
C16 H16 0.9500
C14 H14 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
O4 H4 O1 1.07(2) 1.38(2) 2.4384(17) 172(2) .
C3 H3 O1 0.95 2.39 3.328(2) 168.0 1_565
C5 H5 O1 0.95 2.37 3.273(2) 158.1 3_556
C6 H6 O3 0.95 2.54 3.379(2) 146.8 3_566
C8 H8 O3 0.95 2.55 3.092(2) 116.3 3_666
C9 H9 O3 0.95 2.49 3.0639(19) 118.8 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 -69.19(18)
C5 N1 C2 C3 111.53(15)
C9 N1 C2 C1 113.51(15)
C5 N1 C2 C1 -65.76(16)
C5 N1 C9 C8 -0.6(2)
C2 N1 C9 C8 -179.91(13)
C16 C11 C12 C13 1.8(2)
C10 C11 C12 C13 -177.18(14)
C9 N1 C5 C6 0.0(2)
C2 N1 C5 C6 179.30(13)
N1 C9 C8 C7 -0.2(2)
N1 C2 C3 C4 -177.52(13)
C1 C2 C3 C4 -0.8(3)
O3 C4 C3 C2 161.72(15)
O4 C4 C3 C2 -18.7(2)
N1 C5 C6 C7 1.4(2)
C3 C2 C1 O2 -156.18(16)
N1 C2 C1 O2 20.62(19)
C3 C2 C1 O1 23.0(2)
N1 C2 C1 O1 -160.15(12)
C12 C11 C10 C7 -70.34(18)
C16 C11 C10 C7 110.74(17)
C11 C12 C13 C14 -0.3(2)
C14 C15 C16 C11 0.1(2)
C12 C11 C16 C15 -1.7(2)
C10 C11 C16 C15 177.24(14)
C5 C6 C7 C8 -2.2(2)
C5 C6 C7 C10 173.39(14)
C9 C8 C7 C6 1.6(2)
C9 C8 C7 C10 -173.92(14)
C11 C10 C7 C6 151.04(14)
C11 C10 C7 C8 -33.6(2)
C16 C15 C14 C13 1.4(2)
C12 C13 C14 C15 -1.3(2)
