#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:36:05 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516505.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_4516505
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, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C18 H17 N O5'
_chemical_formula_weight         327.32
_chemical_name_systematic
;
'(2Z)-2-(4-benzylpyridinium-1-yl-3-carboxy-1-hydroxyprop-2-en-1-olate
dioxane solvate'
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 96.588(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.882(2)
_cell_length_b                   7.4417(13)
_cell_length_c                   15.134(3)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.174
_cell_measurement_theta_min      2.7095
_cell_volume                     1553.1(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.912
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9203
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.430
_diffrn_reflns_theta_min         1.886
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2012'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.662
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0485
_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)+(0.0623P)²+1.0885P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2930
_reflns_number_total             3569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01238_si_002.cif
_cod_data_source_block           1_diox
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516505
_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   0.935
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2012-9
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.73561(8) 0.35012(15) 0.64268(8) 0.0180(3) Uani 1 1 d . .
O4 O 0.70772(8) 1.02512(15) 0.62212(8) 0.0198(3) Uani 1 1 d D .
O2 O 0.57367(8) 0.38364(15) 0.61427(8) 0.0171(3) Uani 1 1 d . .
N1 N 0.58284(9) 0.74637(17) 0.64190(9) 0.0127(3) Uani 1 1 d . .
O3 O 0.86198(9) 0.97141(17) 0.67417(9) 0.0242(3) Uani 1 1 d . .
C1 C 0.65657(11) 0.4408(2) 0.63303(10) 0.0140(3) Uani 1 1 d . .
C3 C 0.75761(11) 0.7231(2) 0.64876(10) 0.0147(3) Uani 1 1 d . .
H3 H 0.8122 0.6453 0.6524 0.018 Uiso 1 1 calc R U
C5 C 0.51978(11) 0.7453(2) 0.56679(10) 0.0141(3) Uani 1 1 d . .
H5 H 0.5296 0.6651 0.5198 0.017 Uiso 1 1 calc R U
C2 C 0.67158(11) 0.6426(2) 0.64340(10) 0.0133(3) Uani 1 1 d . .
C6 C 0.44192(11) 0.8594(2) 0.55816(11) 0.0156(3) Uani 1 1 d . .
H6 H 0.3973 0.8567 0.5056 0.019 Uiso 1 1 calc R U
C7 C 0.42780(11) 0.9793(2) 0.62604(11) 0.0156(3) Uani 1 1 d . .
C8 C 0.49154(12) 0.9716(2) 0.70414(11) 0.0178(3) Uani 1 1 d . .
H8 H 0.4819 1.0480 0.7526 0.021 Uiso 1 1 calc R U
C11 C 0.25735(13) 1.0662(2) 0.65480(13) 0.0216(4) Uani 1 1 d . .
C4 C 0.78001(11) 0.9215(2) 0.64989(10) 0.0141(3) Uani 1 1 d . .
C9 C 0.56850(12) 0.8535(2) 0.71120(11) 0.0163(3) Uani 1 1 d . .
H9 H 0.6114 0.8475 0.7647 0.020 Uiso 1 1 calc R U
C15 C 0.16758(16) 1.0616(3) 0.78188(15) 0.0323(5) Uani 1 1 d . .
H15 H 0.1643 1.0857 0.8431 0.039 Uiso 1 1 calc R U
C10 C 0.34721(12) 1.1168(2) 0.61197(12) 0.0202(4) Uani 1 1 d . .
H10A H 0.3289 1.1329 0.5473 0.024 Uiso 1 1 calc R U
H10B H 0.3718 1.2335 0.6365 0.024 Uiso 1 1 calc R U
C16 C 0.25161(15) 1.1017(2) 0.74402(14) 0.0281(4) Uani 1 1 d . .
H16 H 0.3054 1.1537 0.7794 0.034 Uiso 1 1 calc R U
C12 C 0.17801(14) 0.9864(3) 0.60412(14) 0.0282(4) Uani 1 1 d . .
H12 H 0.1815 0.9583 0.5433 0.034 Uiso 1 1 calc R U
C14 C 0.08880(15) 0.9865(3) 0.73076(16) 0.0349(5) Uani 1 1 d . .
H14 H 0.0310 0.9614 0.7565 0.042 Uiso 1 1 calc R U
C13 C 0.09434(14) 0.9484(3) 0.64268(16) 0.0360(5) Uani 1 1 d . .
H13 H 0.0404 0.8956 0.6078 0.043 Uiso 1 1 calc R U
O1A O 0.53119(13) 0.0418(2) 0.91648(9) 0.0398(4) Uani 1 1 d . .
C3A C 0.5797(2) 0.1090(4) 0.99777(15) 0.0497(7) Uani 1 1 d . .
H4A H 0.6074 0.2285 0.9872 0.060 Uiso 1 1 calc R U
H3A H 0.6339 0.0275 1.0189 0.060 Uiso 1 1 calc R U
C1A C 0.4868(2) -0.1246(3) 0.93238(15) 0.0493(7) Uani 1 1 d . .
H1A H 0.5376 -0.2146 0.9511 0.059 Uiso 1 1 calc R U
H2A H 0.4499 -0.1676 0.8765 0.059 Uiso 1 1 calc R U
H4 H 0.725(2) 1.166(2) 0.6308(19) 0.068(9) Uiso 1 1 d 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
_geom_angle_site_symmetry_3
C4 O4 H4 112.3(15) . .
C9 N1 C5 121.14(14) . .
C9 N1 C2 120.15(13) . .
C5 N1 C2 118.44(13) . .
O2 C1 O1 127.64(15) . .
O2 C1 C2 118.60(14) . .
O1 C1 C2 113.72(13) . .
C2 C3 C4 128.59(14) . .
C2 C3 H3 115.7 . .
C4 C3 H3 115.7 . .
N1 C5 C6 120.28(15) . .
N1 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C3 C2 N1 121.06(14) . .
C3 C2 C1 124.18(14) . .
N1 C2 C1 114.66(13) . .
C5 C6 C7 120.26(15) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C6 C7 C8 118.04(15) . .
C6 C7 C10 119.62(15) . .
C8 C7 C10 122.30(15) . .
C9 C8 C7 120.20(15) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C16 C11 C12 118.99(18) . .
C16 C11 C10 120.68(17) . .
C12 C11 C10 120.31(17) . .
O3 C4 O4 125.44(15) . .
O3 C4 C3 119.22(14) . .
O4 C4 C3 115.32(13) . .
N1 C9 C8 119.89(15) . .
N1 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
C14 C15 C16 120.2(2) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C7 C10 C11 113.76(14) . .
C7 C10 H10A 108.8 . .
C11 C10 H10A 108.8 . .
C7 C10 H10B 108.8 . .
C11 C10 H10B 108.8 . .
H10A C10 H10B 107.7 . .
C11 C16 C15 120.3(2) . .
C11 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C13 C12 C11 120.0(2) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C13 C14 C15 119.84(19) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C14 C13 C12 120.6(2) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C1A O1A C3A 109.41(17) . .
O1A C3A C1A 111.8(2) . 3_657
O1A C3A H4A 109.3 . .
C1A C3A H4A 109.3 3_657 .
O1A C3A H3A 109.3 . .
C1A C3A H3A 109.3 3_657 .
H4A C3A H3A 107.9 . .
O1A C1A C3A 111.7(2) . 3_657
O1A C1A H1A 109.3 . .
C3A C1A H1A 109.3 3_657 .
O1A C1A H2A 109.3 . .
C3A C1A H2A 109.3 3_657 .
H1A C1A H2A 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2820(19) .
O4 C4 1.2968(19) .
O4 H4 1.079(18) .
O2 C1 1.2290(19) .
N1 C9 1.350(2) .
N1 C5 1.353(2) .
N1 C2 1.452(2) .
O3 C4 1.213(2) .
C1 C2 1.522(2) .
C3 C2 1.330(2) .
C3 C4 1.509(2) .
C3 H3 0.9500 .
C5 C6 1.369(2) .
C5 H5 0.9500 .
C6 C7 1.391(2) .
C6 H6 0.9500 .
C7 C8 1.394(2) .
C7 C10 1.513(2) .
C8 C9 1.378(2) .
C8 H8 0.9500 .
C11 C16 1.387(3) .
C11 C12 1.400(3) .
C11 C10 1.518(2) .
C9 H9 0.9500 .
C15 C14 1.383(3) .
C15 C16 1.390(3) .
C15 H15 0.9500 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C16 H16 0.9500 .
C12 C13 1.387(3) .
C12 H12 0.9500 .
C14 C13 1.374(3) .
C14 H14 0.9500 .
C13 H13 0.9500 .
O1A C1A 1.416(3) .
O1A C3A 1.424(3) .
C3A C1A 1.486(3) 3_657
C3A H4A 0.9900 .
C3A H3A 0.9900 .
C1A C3A 1.485(3) 3_657
C1A H1A 0.9900 .
C1A H2A 0.9900 .
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 1.079(18) 1.390(18) 2.4634(16) 173(3) 1_565
C5 H5 O2 0.95 2.37 3.049(2) 127.7 3_666
C6 H6 O4 0.95 2.45 3.346(2) 157.7 3_676
C6 H6 O2 0.95 2.61 3.162(2) 117.3 3_666
C8 H8 O1A 0.95 2.50 3.240(2) 135.2 1_565
C9 H9 O1 0.95 2.41 3.302(2) 157.1 2_656
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_4
C9 N1 C5 C6 2.8(2) .
C2 N1 C5 C6 -171.25(14) .
C4 C3 C2 N1 -3.0(3) .
C4 C3 C2 C1 173.29(15) .
C9 N1 C2 C3 -60.8(2) .
C5 N1 C2 C3 113.30(17) .
C9 N1 C2 C1 122.53(15) .
C5 N1 C2 C1 -63.33(18) .
O2 C1 C2 C3 -168.29(15) .
O1 C1 C2 C3 9.5(2) .
O2 C1 C2 N1 8.2(2) .
O1 C1 C2 N1 -173.94(13) .
N1 C5 C6 C7 1.0(2) .
C5 C6 C7 C8 -3.8(2) .
C5 C6 C7 C10 174.04(15) .
C6 C7 C8 C9 2.9(2) .
C10 C7 C8 C9 -174.84(15) .
C2 C3 C4 O3 164.14(17) .
C2 C3 C4 O4 -17.3(2) .
C5 N1 C9 C8 -3.7(2) .
C2 N1 C9 C8 170.29(15) .
C7 C8 C9 N1 0.7(2) .
C6 C7 C10 C11 100.82(18) .
C8 C7 C10 C11 -81.5(2) .
C16 C11 C10 C7 83.5(2) .
C12 C11 C10 C7 -98.0(2) .
C12 C11 C16 C15 -1.2(3) .
C10 C11 C16 C15 177.41(17) .
C14 C15 C16 C11 -0.3(3) .
C16 C11 C12 C13 1.7(3) .
C10 C11 C12 C13 -176.90(17) .
C16 C15 C14 C13 1.2(3) .
C15 C14 C13 C12 -0.7(3) .
C11 C12 C13 C14 -0.8(3) .
C1A O1A C3A C1A -55.7(3) 3_657
C3A O1A C1A C3A 55.6(3) 3_657
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 1.000 145 44 ' '
2 1.000 0.500 0.500 145 44 ' '
