#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/61/2216160.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2216160
loop_
_publ_author_name
'Ejsmont, Krzysztof'
'Zaleski Jacek'
_publ_section_title
;
 Tetrakis(tert-butylammonium) benzene-1,2,4,5-tetracarboxylate
 octahydrate
;
_journal_coeditor_code           WN2206
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4315
_journal_page_last               o4315
_journal_paper_doi               10.1107/S1600536807049690
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '4C4 H12 N +, C10 H2 O8 4-, 8H2 O'
_chemical_formula_moiety         '4(C4 H12 N +), C10 H2 O8 4-, 8(H2 O)'
_chemical_formula_sum            'C26 H66 N4 O16'
_chemical_formula_weight         690.83
_chemical_name_systematic
;
Tetrakis(tert-butylammonium) benzene-1,2,4,5-tetracarboxylate octahydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 100.612(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2536(13)
_cell_length_b                   10.6867(14)
_cell_length_c                   18.213(2)
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.31
_cell_volume                     1961.6(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11870
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.200
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0628P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2640
_reflns_number_total             3450
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2206.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C26 H66 N4 O16 '
_cod_database_code               2216160
_cod_database_fobs_code          2216160
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.67535(9) 0.52249(10) 0.05853(6) 0.0391(3) Uani d . 1
O O2 0.83267(10) 0.59772(10) 0.14832(6) 0.0389(3) Uani d . 1
O O3 1.15184(10) 0.38914(11) 0.18681(6) 0.0446(3) Uani d . 1
O O4 0.94210(10) 0.32573(11) 0.16479(6) 0.0441(3) Uani d . 1
O O5 0.42524(12) 0.61807(11) 0.06639(7) 0.0412(3) Uani d . 1
O O6 0.70600(12) 0.09759(12) 0.31228(7) 0.0421(3) Uani d . 1
O O7 0.68835(11) 0.71383(11) 0.23518(7) 0.0404(3) Uani d . 1
O O8 0.49939(17) 0.85094(13) 0.13795(10) 0.0695(5) Uani d . 1
N N9 0.49549(14) 0.09957(13) 0.18813(8) 0.0365(3) Uani d . 1
N N10 0.94341(14) 0.25188(13) 0.31131(8) 0.0337(3) Uani d . 1
C C11 0.89899(12) 0.51179(12) 0.04206(7) 0.0233(3) Uani d . 1
C C12 1.01639(12) 0.44950(12) 0.07267(7) 0.0241(3) Uani d . 1
C C13 1.11574(13) 0.44063(13) 0.03004(8) 0.0256(3) Uani d . 1
C C14 0.79351(13) 0.54353(13) 0.08678(8) 0.0262(3) Uani d . 1
C C15 1.03681(13) 0.38363(13) 0.14770(8) 0.0287(3) Uani d . 1
C C16 0.51441(16) 0.18556(16) 0.12506(9) 0.0436(4) Uani d . 1
C C17 0.3934(2) 0.1708(2) 0.06386(12) 0.0757(7) Uani d . 1
H H17A 0.3892 0.0865 0.0453 0.114 Uiso calc R 1
H H17B 0.3995 0.2277 0.0239 0.114 Uiso calc R 1
H H17C 0.3149 0.1888 0.0836 0.114 Uiso calc R 1
C C18 0.6396(2) 0.1463(2) 0.09859(13) 0.0690(6) Uani d . 1
H H18A 0.7143 0.1567 0.1384 0.103 Uiso calc R 1
H H18B 0.6513 0.1972 0.0569 0.103 Uiso calc R 1
H H18C 0.6326 0.0600 0.0837 0.103 Uiso calc R 1
C C19 0.5257(2) 0.31708(18) 0.15633(14) 0.0803(7) Uani d . 1
H H19A 0.6031 0.3232 0.1948 0.120 Uiso calc R 1
H H19B 0.4482 0.3362 0.1769 0.120 Uiso calc R 1
H H19C 0.5328 0.3753 0.1171 0.120 Uiso calc R 1
C C20 0.94694(15) 0.36444(15) 0.36155(9) 0.0399(4) Uani d . 1
C C21 0.8410(2) 0.4540(2) 0.32339(12) 0.0776(7) Uani d . 1
H H21A 0.8619 0.4802 0.2765 0.116 Uiso calc R 1
H H21B 0.8376 0.5258 0.3547 0.116 Uiso calc R 1
H H21C 0.7564 0.4126 0.3148 0.116 Uiso calc R 1
C C22 1.0831(2) 0.4206(2) 0.36966(15) 0.0862(8) Uani d . 1
H H22A 1.1477 0.3619 0.3941 0.129 Uiso calc R 1
H H22B 1.0872 0.4957 0.3989 0.129 Uiso calc R 1
H H22C 1.1015 0.4402 0.3211 0.129 Uiso calc R 1
C C23 0.9167(2) 0.3219(2) 0.43570(10) 0.0664(6) Uani d . 1
H H23A 0.9850 0.2659 0.4592 0.100 Uiso calc R 1
H H23B 0.8327 0.2796 0.4278 0.100 Uiso calc R 1
H H23C 0.9132 0.3933 0.4673 0.100 Uiso calc R 1
H H5A 0.3778(19) 0.5768(18) 0.0226(12) 0.059(6) Uiso d . 1
H H5B 0.507(2) 0.5916(19) 0.0704(12) 0.074(7) Uiso d . 1
H H6A 0.751(2) 0.026(2) 0.3165(11) 0.071(7) Uiso d . 1
H H6B 0.660(2) 0.104(2) 0.3518(14) 0.087(8) Uiso d . 1
H H7A 0.737(2) 0.666(2) 0.2081(15) 0.105(8) Uiso d . 1
H H7B 0.751(2) 0.7683(19) 0.2594(11) 0.062(6) Uiso d . 1
H H8A 0.558(2) 0.807(3) 0.1686(14) 0.091(8) Uiso d . 1
H H8B 0.458(2) 0.791(3) 0.1067(14) 0.095(8) Uiso d . 1
H H9A 0.4809(18) 0.015(2) 0.1731(11) 0.072(6) Uiso d . 1
H H9B 0.4187(19) 0.1320(17) 0.2084(11) 0.059(5) Uiso d . 1
H H9C 0.5688(18) 0.1004(15) 0.2283(11) 0.048(5) Uiso d . 1
H H10A 1.0180(17) 0.2004(17) 0.3286(9) 0.049(5) Uiso d . 1
H H10B 0.9470(16) 0.2775(16) 0.2620(12) 0.051(5) Uiso d . 1
H H10C 0.8628(19) 0.2081(18) 0.3101(10) 0.060(6) Uiso d . 1
H H13 1.1952(16) 0.3948(14) 0.0502(9) 0.039(4) Uiso d . 1
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_site_symmetry_1
_geom_angle
H5A O5 H5B . 104.5(18)
H6A O6 H6B . 108.7(18)
H7A O7 H7B . 102.0(19)
H8A O8 H8B . 102(2)
C16 N9 H9A . 113.4(12)
C16 N9 H9B . 107.0(11)
H9A N9 H9B . 110.3(15)
C16 N9 H9C . 112.7(10)
H9A N9 H9C . 106.9(15)
H9B N9 H9C . 106.3(16)
C20 N10 H10A . 109.5(10)
C20 N10 H10B . 110.1(11)
H10A N10 H10B . 108.3(14)
C20 N10 H10C . 109.4(11)
H10A N10 H10C . 111.6(16)
H10B N10 H10C . 107.9(15)
C13 C11 C12 3_765 119.11(12)
C13 C11 C14 3_765 117.65(12)
C12 C11 C14 . 122.84(12)
C13 C12 C11 . 118.32(12)
C13 C12 C15 . 118.47(12)
C11 C12 C15 . 123.08(11)
C11 C13 C12 3_765 122.56(13)
C11 C13 H13 3_765 118.9(10)
C12 C13 H13 . 118.4(9)
O1 C14 O2 . 125.20(12)
O1 C14 C11 . 118.42(12)
O2 C14 C11 . 116.18(12)
O4 C15 O3 . 125.17(13)
O4 C15 C12 . 118.27(12)
O3 C15 C12 . 116.51(12)
C18 C16 N9 . 108.00(14)
C18 C16 C19 . 111.58(16)
N9 C16 C19 . 106.88(15)
C18 C16 C17 . 111.39(17)
N9 C16 C17 . 107.07(14)
C19 C16 C17 . 111.64(17)
C16 C17 H17A . 109.5
C16 C17 H17B . 109.5
H17A C17 H17B . 109.5
C16 C17 H17C . 109.5
H17A C17 H17C . 109.5
H17B C17 H17C . 109.5
C16 C18 H18A . 109.5
C16 C18 H18B . 109.5
H18A C18 H18B . 109.5
C16 C18 H18C . 109.5
H18A C18 H18C . 109.5
H18B C18 H18C . 109.5
C16 C19 H19A . 109.5
C16 C19 H19B . 109.5
H19A C19 H19B . 109.5
C16 C19 H19C . 109.5
H19A C19 H19C . 109.5
H19B C19 H19C . 109.5
C22 C20 N10 . 107.26(14)
C22 C20 C23 . 111.87(17)
N10 C20 C23 . 108.46(14)
C22 C20 C21 . 111.55(18)
N10 C20 C21 . 106.86(14)
C23 C20 C21 . 110.61(15)
C20 C21 H21A . 109.5
C20 C21 H21B . 109.5
H21A C21 H21B . 109.5
C20 C21 H21C . 109.5
H21A C21 H21C . 109.5
H21B C21 H21C . 109.5
C20 C22 H22A . 109.5
C20 C22 H22B . 109.5
H22A C22 H22B . 109.5
C20 C22 H22C . 109.5
H22A C22 H22C . 109.5
H22B C22 H22C . 109.5
C20 C23 H23A . 109.5
C20 C23 H23B . 109.5
H23A C23 H23B . 109.5
C20 C23 H23C . 109.5
H23A C23 H23C . 109.5
H23B C23 H23C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C14 . 1.2464(16)
O2 C14 . 1.2598(17)
O3 C15 . 1.2619(17)
O4 C15 . 1.2386(17)
O5 H5A . 0.96(2)
O5 H5B . 0.88(2)
O6 H6A . 0.89(2)
O6 H6B . 0.93(3)
O7 H7A . 0.92(3)
O7 H7B . 0.92(2)
O8 H8A . 0.87(3)
O8 H8B . 0.91(3)
N9 C16 . 1.511(2)
N9 H9A . 0.95(2)
N9 H9B . 0.99(2)
N9 H9C . 0.947(19)
N10 C20 . 1.508(2)
N10 H10A . 0.947(18)
N10 H10B . 0.95(2)
N10 H10C . 0.95(2)
C11 C13 3_765 1.3902(19)
C11 C12 . 1.3985(18)
C11 C14 . 1.5075(18)
C12 C13 . 1.3932(19)
C12 C15 . 1.5171(18)
C13 C11 3_765 1.3902(19)
C13 H13 . 0.964(16)
C16 C18 . 1.511(2)
C16 C19 . 1.513(3)
C16 C17 . 1.516(3)
C17 H17A . 0.9600
C17 H17B . 0.9600
C17 H17C . 0.9600
C18 H18A . 0.9600
C18 H18B . 0.9600
C18 H18C . 0.9600
C19 H19A . 0.9600
C19 H19B . 0.9600
C19 H19C . 0.9600
C20 C22 . 1.502(3)
C20 C23 . 1.510(2)
C20 C21 . 1.517(2)
C21 H21A . 0.9600
C21 H21B . 0.9600
C21 H21C . 0.9600
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
C23 H23A . 0.9600
C23 H23B . 0.9600
C23 H23C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5A O1 3_665 0.96(2) 1.82(2) 2.7626(16) 166.2(17)
O5 H5B O1 . 0.88(2) 1.93(2) 2.7885(15) 168(2)
O6 H6A O3 2_745 0.89(2) 1.78(2) 2.6606(17) 171.9(19)
O6 H6B O5 2_645 0.93(3) 1.87(3) 2.7994(17) 178(2)
O7 H7A O2 . 0.92(3) 1.75(3) 2.6635(15) 170(2)
O7 H7B O3 2_755 0.92(2) 1.80(2) 2.7122(16) 168.9(18)
O8 H8A O7 . 0.87(3) 1.92(3) 2.788(2) 179(2)
O8 H8B O5 . 0.91(3) 2.00(3) 2.8469(19) 156(2)
N9 H9A O8 1_545 0.95(2) 1.89(2) 2.813(2) 164.3(16)
N9 H9B O7 2_645 0.99(2) 1.86(2) 2.8223(18) 164.2(16)
N9 H9C O6 . 0.947(19) 1.88(2) 2.8240(19) 175.9(16)
N10 H10A O2 2_745 0.947(18) 1.868(18) 2.8115(17) 173.6(15)
N10 H10B O4 . 0.95(2) 1.84(2) 2.7805(17) 176.2(15)
N10 H10C O6 . 0.95(2) 2.00(2) 2.9429(18) 173.0(17)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C11 C12 C13 3_765 . 1.7(2) ?
C14 C11 C12 C13 . . -170.81(12) ?
C13 C11 C12 C15 3_765 . -173.97(12) ?
C14 C11 C12 C15 . . 13.5(2) ?
C11 C12 C13 C11 . 3_765 -1.8(2) ?
C15 C12 C13 C11 . 3_765 174.11(12) ?
C13 C11 C14 O1 3_765 . 52.61(18) ?
C12 C11 C14 O1 . . -134.78(14) y
C13 C11 C14 O2 3_765 . -122.65(14) ?
C12 C11 C14 O2 . . 49.96(18) y
C13 C12 C15 O4 . . -137.18(14) ?
C11 C12 C15 O4 . . 38.47(19) y
C13 C12 C15 O3 . . 40.48(18) y
C11 C12 C15 O3 . . -143.86(13) ?
