#------------------------------------------------------------------------------
#$Date: 2022-11-15 11:00:05 +0200 (Tue, 15 Nov 2022) $
#$Revision: 279286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106092.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_8106092
loop_
_publ_author_name
'Liu, Yalin'
'Li, Qiufang'
_publ_section_title
;
 Crystal structure of tetrapropylammonium 5-hydroxyisophthalate
 tetrahydrate, C20H41NO9
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              183
_journal_page_last               184
_journal_paper_doi               10.1515/ncrs-2017-0151
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C12 H28 N, C8 H5 O5, 4(H2 O)'
_chemical_formula_sum            'C20 H41 N O9'
_chemical_formula_weight         439.54
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.371(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.475(7)
_cell_length_b                   8.582(4)
_cell_length_c                   17.579(8)
_cell_measurement_reflns_used    3641
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.15
_cell_measurement_theta_min      2.38
_cell_volume                     2418.1(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15144
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.184
_diffrn_reflns_theta_max         25.184
_diffrn_reflns_theta_min         1.527
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method water/ethanol(v/v:1:2)
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0456
_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)+(0.0630P)²+0.3698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2839
_reflns_number_total             4315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0151_suppl.cif
_cod_data_source_block           exp_266_109
_cod_original_cell_volume        2418.1(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106092
_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   0.953
_shelx_estimated_absorpt_t_max   0.976
_exptl_absorpt_special_details   'Bruker, 2000'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31984(10) 0.6669(2) 0.03469(10) 0.0385(4) Uani 1 1 d . . . . .
O1 O 0.44719(9) 0.5426(2) 0.03540(8) 0.0791(6) Uani 1 1 d . . . . .
H1 H 0.5000 0.5000 0.0000 0.119 Uiso 1 2 d S U P . .
O1W O 0.07961(10) 0.0043(2) 0.20287(8) 0.0656(5) Uani 1 1 d D . . . .
H1WA H 0.0406(12) 0.015(4) 0.2279(12) 0.098 Uiso 1 1 d D U . . .
H1WB H 0.0593(14) 0.011(4) 0.1542(6) 0.098 Uiso 1 1 d D U . . .
N1 N -0.00349(9) 0.52472(19) 0.24763(9) 0.0456(4) Uani 1 1 d . . . . .
C2 C 0.25065(10) 0.7504(2) -0.00498(10) 0.0411(5) Uani 1 1 d . . . . .
H2A H 0.2434 0.7708 -0.0581 0.049 Uiso 1 1 calc R U . . .
O2 O 0.37563(9) 0.6280(2) -0.07709(8) 0.0789(6) Uani 1 1 d . . . . .
O2W O 0.52832(10) 0.5029(3) 0.19986(10) 0.0792(6) Uani 1 1 d D . . . .
H2WA H 0.5778(10) 0.531(4) 0.2247(14) 0.119 Uiso 1 1 d D U . . .
H2WB H 0.5235(17) 0.507(4) 0.1506(6) 0.119 Uiso 1 1 d D U . . .
C3 C 0.19223(10) 0.8035(2) 0.03492(10) 0.0371(4) Uani 1 1 d . . . . .
O3 O 0.10182(9) 0.9120(2) -0.07853(8) 0.0701(5) Uani 1 1 d . . . . .
O3W O 0.27031(11) 0.6887(2) 0.78375(9) 0.0752(5) Uani 1 1 d D . . . .
H3WA H 0.2988(16) 0.672(3) 0.8305(7) 0.113 Uiso 1 1 d D U . . .
H3WB H 0.2804(18) 0.617(3) 0.7532(13) 0.113 Uiso 1 1 d D U . . .
C4 C 0.20407(10) 0.7745(2) 0.11382(10) 0.0406(5) Uani 1 1 d . . . . .
H4A H 0.1660 0.8128 0.1409 0.049 Uiso 1 1 calc R U . . .
O4 O 0.06541(8) 0.93283(19) 0.03431(7) 0.0577(4) Uani 1 1 d . . . . .
H4 H 0.0000 1.0000 0.0000 0.087 Uiso 1 2 d S U P . .
O4W O 0.18113(10) 0.9444(2) 0.79934(9) 0.0697(5) Uani 1 1 d D . . . .
H4WA H 0.2074(16) 0.860(2) 0.7912(15) 0.105 Uiso 1 1 d D U . . .
H4WB H 0.1639(16) 0.933(3) 0.8418(10) 0.105 Uiso 1 1 d D U . . .
C5 C 0.27212(10) 0.6890(2) 0.15315(10) 0.0406(5) Uani 1 1 d . . . . .
O5 O 0.27910(9) 0.6619(2) 0.23067(8) 0.0646(5) Uani 1 1 d D . . . .
H5 H 0.3232(11) 0.608(3) 0.2503(14) 0.097 Uiso 1 1 d D U . . .
C6 C 0.32970(10) 0.6352(2) 0.11337(10) 0.0395(5) Uani 1 1 d . . . . .
H6A H 0.3753 0.5773 0.1397 0.047 Uiso 1 1 calc R U . . .
C7 C 0.38399(11) 0.6096(3) -0.00748(11) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.11544(11) 0.8905(3) -0.00807(11) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.03313(13) 0.4133(3) 0.19817(13) 0.0546(5) Uani 1 1 d . . . . .
H9A H 0.0745 0.3494 0.2326 0.066 Uiso 1 1 calc R U . . .
H9B H -0.0109 0.3444 0.1712 0.066 Uiso 1 1 calc R U . . .
C10 C 0.07318(17) 0.4873(3) 0.13858(15) 0.0777(8) Uani 1 1 d . . . . .
H10A H 0.1235 0.5413 0.1651 0.093 Uiso 1 1 calc R U . . .
H10B H 0.0353 0.5634 0.1087 0.093 Uiso 1 1 calc R U . . .
C11 C 0.09466(18) 0.3672(4) 0.08404(17) 0.0991(10) Uani 1 1 d . . . . .
H11A H 0.1201 0.4175 0.0466 0.149 Uiso 1 1 calc R U . . .
H11B H 0.1328 0.2927 0.1135 0.149 Uiso 1 1 calc R U . . .
H11C H 0.0448 0.3148 0.0572 0.149 Uiso 1 1 calc R U . . .
C12 C -0.06974(13) 0.6278(3) 0.19743(12) 0.0567(6) Uani 1 1 d . . . . .
H12A H -0.0968 0.6864 0.2318 0.068 Uiso 1 1 calc R U . . .
H12B H -0.0421 0.7024 0.1705 0.068 Uiso 1 1 calc R U . . .
C13 C -0.13582(15) 0.5469(3) 0.13781(14) 0.0720(7) Uani 1 1 d . . . . .
H13A H -0.1650 0.4725 0.1634 0.086 Uiso 1 1 calc R U . . .
H13B H -0.1105 0.4906 0.1014 0.086 Uiso 1 1 calc R U . . .
C14 C -0.19673(16) 0.6658(4) 0.09417(15) 0.0909(9) Uani 1 1 d . . . . .
H14A H -0.2392 0.6140 0.0559 0.136 Uiso 1 1 calc R U . . .
H14B H -0.2221 0.7205 0.1304 0.136 Uiso 1 1 calc R U . . .
H14C H -0.1677 0.7385 0.0685 0.136 Uiso 1 1 calc R U . . .
C15 C -0.04024(13) 0.4250(3) 0.30233(12) 0.0566(6) Uani 1 1 d . . . . .
H15A H -0.0845 0.3621 0.2710 0.068 Uiso 1 1 calc R U . . .
H15B H 0.0027 0.3542 0.3294 0.068 Uiso 1 1 calc R U . . .
C16 C -0.07493(17) 0.5098(4) 0.36239(15) 0.0849(9) Uani 1 1 d . . . . .
H16A H -0.1224 0.5721 0.3364 0.102 Uiso 1 1 calc R U . . .
H16B H -0.0328 0.5796 0.3918 0.102 Uiso 1 1 calc R U . . .
C17 C -0.10165(19) 0.3976(5) 0.41743(17) 0.1129(12) Uani 1 1 d . . . . .
H17A H -0.1236 0.4545 0.4552 0.169 Uiso 1 1 calc R U . . .
H17B H -0.1439 0.3296 0.3885 0.169 Uiso 1 1 calc R U . . .
H17C H -0.0545 0.3370 0.4438 0.169 Uiso 1 1 calc R U . . .
C18 C 0.06234(13) 0.6345(3) 0.29312(12) 0.0548(5) Uani 1 1 d . . . . .
H18A H 0.0843 0.6952 0.2559 0.066 Uiso 1 1 calc R U . . .
H18B H 0.0352 0.7066 0.3218 0.066 Uiso 1 1 calc R U . . .
C19 C 0.13419(14) 0.5619(3) 0.34966(14) 0.0662(6) Uani 1 1 d . . . . .
H19A H 0.1662 0.4981 0.3216 0.079 Uiso 1 1 calc R U . . .
H19B H 0.1136 0.4953 0.3856 0.079 Uiso 1 1 calc R U . . .
C20 C 0.18949(15) 0.6874(3) 0.39478(15) 0.0799(8) Uani 1 1 d . . . . .
H20A H 0.2355 0.6399 0.4310 0.120 Uiso 1 1 calc R U . . .
H20B H 0.2103 0.7523 0.3591 0.120 Uiso 1 1 calc R U . . .
H20C H 0.1578 0.7495 0.4230 0.120 Uiso 1 1 calc R U . . .
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
C6 C1 C2 119.79(15) . .
C6 C1 C7 119.64(16) . .
C2 C1 C7 120.57(16) . .
C7 O1 H1 114.21(14) . .
H1WA O1W H1WB 109.9(19) . .
C9 N1 C15 106.23(17) . .
C9 N1 C18 111.41(16) . .
C15 N1 C18 111.00(16) . .
C9 N1 C12 111.33(16) . .
C15 N1 C12 111.04(16) . .
C18 N1 C12 105.93(16) . .
C1 C2 C3 119.89(16) . .
C1 C2 H2A 120.1 . .
C3 C2 H2A 120.1 . .
H2WA O2W H2WB 111(2) . .
C4 C3 C2 119.65(16) . .
C4 C3 C8 119.97(15) . .
C2 C3 C8 120.38(16) . .
H3WA O3W H3WB 109(2) . .
C3 C4 C5 120.56(16) . .
C3 C4 H4A 119.7 . .
C5 C4 H4A 119.7 . .
C8 O4 H4 116.65(13) . .
H4WA O4W H4WB 109(2) . .
O5 C5 C6 122.74(16) . .
O5 C5 C4 117.51(15) . .
C6 C5 C4 119.75(17) . .
C5 O5 H5 111.1(17) . .
C5 C6 C1 120.34(17) . .
C5 C6 H6A 119.8 . .
C1 C6 H6A 119.8 . .
O2 C7 O1 122.97(17) . .
O2 C7 C1 121.76(17) . .
O1 C7 C1 115.26(16) . .
O3 C8 O4 123.64(17) . .
O3 C8 C3 121.17(16) . .
O4 C8 C3 115.12(16) . .
C10 C9 N1 115.6(2) . .
C10 C9 H9A 108.4 . .
N1 C9 H9A 108.4 . .
C10 C9 H9B 108.4 . .
N1 C9 H9B 108.4 . .
H9A C9 H9B 107.4 . .
C9 C10 C11 111.2(2) . .
C9 C10 H10A 109.4 . .
C11 C10 H10A 109.4 . .
C9 C10 H10B 109.4 . .
C11 C10 H10B 109.4 . .
H10A C10 H10B 108.0 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 N1 116.4(2) . .
C13 C12 H12A 108.2 . .
N1 C12 H12A 108.2 . .
C13 C12 H12B 108.2 . .
N1 C12 H12B 108.2 . .
H12A C12 H12B 107.3 . .
C12 C13 C14 109.4(2) . .
C12 C13 H13A 109.8 . .
C14 C13 H13A 109.8 . .
C12 C13 H13B 109.8 . .
C14 C13 H13B 109.8 . .
H13A C13 H13B 108.2 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 N1 116.5(2) . .
C16 C15 H15A 108.2 . .
N1 C15 H15A 108.2 . .
C16 C15 H15B 108.2 . .
N1 C15 H15B 108.2 . .
H15A C15 H15B 107.3 . .
C15 C16 C17 111.0(3) . .
C15 C16 H16A 109.4 . .
C17 C16 H16A 109.4 . .
C15 C16 H16B 109.4 . .
C17 C16 H16B 109.4 . .
H16A C16 H16B 108.0 . .
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 . .
C19 C18 N1 116.82(19) . .
C19 C18 H18A 108.1 . .
N1 C18 H18A 108.1 . .
C19 C18 H18B 108.1 . .
N1 C18 H18B 108.1 . .
H18A C18 H18B 107.3 . .
C18 C19 C20 109.9(2) . .
C18 C19 H19A 109.7 . .
C20 C19 H19A 109.7 . .
C18 C19 H19B 109.7 . .
C20 C19 H19B 109.7 . .
H19A C19 H19B 108.2 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.382(2) .
C1 C2 1.390(2) .
C1 C7 1.507(2) .
O1 C7 1.273(2) .
O1 H1 1.2363(13) .
O1W H1WA 0.864(9) .
O1W H1WB 0.846(9) .
N1 C9 1.509(3) .
N1 C15 1.514(3) .
N1 C18 1.517(3) .
N1 C12 1.519(3) .
C2 C3 1.392(2) .
C2 H2A 0.9300 .
O2 C7 1.210(2) .
O2W H2WA 0.864(10) .
O2W H2WB 0.851(10) .
C3 C4 1.378(2) .
C3 C8 1.512(2) .
O3 C8 1.221(2) .
O3W H3WA 0.859(10) .
O3W H3WB 0.859(10) .
C4 C5 1.384(3) .
C4 H4A 0.9300 .
O4 C8 1.285(2) .
O4 H4 1.2476(13) .
O4W H4WA 0.868(10) .
O4W H4WB 0.863(10) .
C5 O5 1.361(2) .
C5 C6 1.382(2) .
O5 H5 0.865(10) .
C6 H6A 0.9300 .
C9 C10 1.502(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.504(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.496(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.510(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 C16 1.500(3) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.501(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C19 1.494(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.512(3) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
