#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017416.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_2017416
loop_
_publ_author_name
'Zheng, Ze-Bao'
'Zhao, Xue'
'Li, Ji-Kun'
'Han, Yin-Feng'
'Ji, Ning-Ning'
_publ_section_title
;
 1:1 Adducts of 2,2'-[isopropylidenebis(p-phenyleneoxy)]diacetic
 acid with dimethylammonium and 4,4'-bipyridine
;
_journal_coeditor_code           SU3040
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o569
_journal_page_last               o573
_journal_paper_doi               10.1107/S0108270109040761
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C2 H8 N + , C19 H19 O6 -'
_chemical_formula_moiety         'C2 H8 N + , C19 H19 O6 -'
_chemical_formula_sum            'C21 H27 N O6'
_chemical_formula_weight         389.44
_chemical_name_systematic
;dimethylammonium
 2-{4-[1-(4-carboxymethoxyphenyl)-1-methylethyl]phenoxy}acetate
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 120.21(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9028(14)
_cell_length_b                   27.756(6)
_cell_length_c                   12.624(4)
_cell_measurement_reflns_used    1412
_cell_measurement_temperature    295
_cell_measurement_theta_max      21.07
_cell_measurement_theta_min      2.94
_cell_volume                     2090.2(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10877
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.47
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0488
_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)+(0.0596P)²+0.0341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2126
_reflns_number_total             3693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3040.cif
_cod_data_source_block           I
_cod_original_cell_volume        2090.2(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017416
_cod_database_fobs_code          2017416
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2193(3) 0.95382(7) 0.42290(16) 0.0730(6) Uani d . 1 . .
O O2 0.4092(2) 0.96870(6) 0.32783(15) 0.0559(5) Uani d . 1 . .
O O3 0.7206(2) 0.90150(6) 0.45967(14) 0.0555(5) Uani d . 1 . .
O O4 0.7744(3) 0.53223(7) 0.43833(16) 0.0725(5) Uani d . 1 . .
O O5 0.8680(3) 0.53345(6) 0.29336(15) 0.0601(5) Uani d . 1 . .
H H5 0.7748 0.5118 0.2629 0.090 Uiso d R 1 . .
O O6 1.1384(3) 0.60835(6) 0.39396(16) 0.0669(5) Uani d . 1 . .
N N1 0.7816(3) 0.98577(8) 0.30070(18) 0.0651(6) Uani d . 1 . .
H H1A 0.6973 0.9735 0.3301 0.078 Uiso d R 1 . .
H H1B 0.9231 0.9754 0.3495 0.078 Uiso d R 1 . .
C C1 0.3801(4) 0.94797(9) 0.4074(2) 0.0470(6) Uani d . 1 . .
C C2 0.5586(4) 0.91318(9) 0.4934(2) 0.0538(7) Uani d . 1 . .
H H2A 0.6349 0.9270 0.5751 0.065 Uiso calc R 1 . .
H H2B 0.4865 0.8837 0.4970 0.065 Uiso calc R 1 . .
C C3 0.6648(4) 0.86726(8) 0.3704(2) 0.0460(6) Uani d . 1 . .
C C4 0.8409(4) 0.84983(9) 0.3592(2) 0.0570(7) Uani d . 1 . .
H H4 0.9855 0.8611 0.4108 0.068 Uiso calc R 1 . .
C C5 0.8028(4) 0.81587(9) 0.2722(2) 0.0564(7) Uani d . 1 . .
H H5A 0.9238 0.8042 0.2668 0.068 Uiso calc R 1 . .
C C6 0.5898(4) 0.79809(8) 0.1916(2) 0.0471(6) Uani d . 1 . .
C C7 0.4184(4) 0.81615(9) 0.2051(2) 0.0546(7) Uani d . 1 . .
H H7 0.2736 0.8050 0.1532 0.066 Uiso calc R 1 . .
C C8 0.4521(4) 0.85036(9) 0.2931(2) 0.0538(6) Uani d . 1 . .
H H8 0.3318 0.8617 0.2997 0.065 Uiso calc R 1 . .
C C9 0.5619(4) 0.75964(9) 0.0977(2) 0.0532(6) Uani d . 1 . .
C C10 0.3186(4) 0.74245(10) 0.0195(2) 0.0723(8) Uani d . 1 . .
H H10A 0.3105 0.7179 -0.0361 0.109 Uiso calc R 1 . .
H H10B 0.2252 0.7691 -0.0262 0.109 Uiso calc R 1 . .
H H10C 0.2678 0.7296 0.0719 0.109 Uiso calc R 1 . .
C C11 0.6308(5) 0.78168(10) 0.0099(2) 0.0790(9) Uani d . 1 . .
H H11A 0.7844 0.7919 0.0556 0.119 Uiso calc R 1 . .
H H11B 0.5370 0.8089 -0.0311 0.119 Uiso calc R 1 . .
H H11C 0.6139 0.7580 -0.0497 0.119 Uiso calc R 1 . .
C C12 0.7102(4) 0.71674(8) 0.1689(2) 0.0472(6) Uani d . 1 . .
C C13 0.8967(4) 0.70208(9) 0.1646(2) 0.0572(7) Uani d . 1 . .
H H13 0.9317 0.7172 0.1106 0.069 Uiso calc R 1 . .
C C14 1.0327(4) 0.66550(9) 0.2385(3) 0.0610(7) Uani d . 1 . .
H H14 1.1575 0.6563 0.2336 0.073 Uiso calc R 1 . .
C C15 0.9863(4) 0.64252(8) 0.3191(2) 0.0513(6) Uani d . 1 . .
C C16 0.7964(4) 0.65502(9) 0.3220(2) 0.0556(7) Uani d . 1 . .
H H16 0.7580 0.6387 0.3732 0.067 Uiso calc R 1 . .
C C17 0.6637(4) 0.69186(9) 0.2484(2) 0.0537(6) Uani d . 1 . .
H H17 0.5371 0.7004 0.2522 0.064 Uiso calc R 1 . .
C C18 0.8879(4) 0.54642(9) 0.3980(2) 0.0527(6) Uani d . 1 . .
C C19 1.0778(4) 0.58096(9) 0.4678(2) 0.0681(8) Uani d . 1 . .
H H19A 1.0367 0.6029 0.5129 0.082 Uiso calc R 1 . .
H H19B 1.2079 0.5629 0.5271 0.082 Uiso calc R 1 . .
C C20 0.6992(5) 0.96651(12) 0.1766(2) 0.0796(9) Uani d . 1 . .
H H20A 0.5526 0.9792 0.1220 0.119 Uiso calc R 1 . .
H H20B 0.6916 0.9320 0.1784 0.119 Uiso calc R 1 . .
H H20C 0.7997 0.9757 0.1484 0.119 Uiso calc R 1 . .
C C21 0.7791(5) 1.03860(11) 0.3086(3) 0.0759(8) Uani d . 1 . .
H H21A 0.8740 1.0522 0.2810 0.114 Uiso calc R 1 . .
H H21B 0.8330 1.0480 0.3921 0.114 Uiso calc R 1 . .
H H21C 0.6287 1.0501 0.2579 0.114 Uiso calc R 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O3 C2 . . 117.80(18) ?
C18 O5 H5 . . 109.5 ?
C15 O6 C19 . . 116.4(2) ?
C21 N1 C20 . . 115.0(2) ?
C21 N1 H1A . . 108.5 ?
C20 N1 H1A . . 108.5 ?
C21 N1 H1B . . 108.5 ?
C20 N1 H1B . . 108.5 ?
H1A N1 H1B . . 107.5 ?
O1 C1 O2 . . 125.8(2) ?
O1 C1 C2 . . 116.4(2) ?
O2 C1 C2 . . 117.8(2) ?
O3 C2 C1 . . 114.2(2) ?
O3 C2 H2A . . 108.7 ?
C1 C2 H2A . . 108.7 ?
O3 C2 H2B . . 108.7 ?
C1 C2 H2B . . 108.7 ?
H2A C2 H2B . . 107.6 ?
C8 C3 O3 . . 125.3(2) ?
C8 C3 C4 . . 119.3(2) ?
O3 C3 C4 . . 115.4(2) ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 122.5(2) ?
C4 C5 H5A . . 118.8 ?
C6 C5 H5A . . 118.8 ?
C7 C6 C5 . . 116.1(2) ?
C7 C6 C9 . . 124.7(2) ?
C5 C6 C9 . . 119.2(2) ?
C6 C7 C8 . . 122.8(2) ?
C6 C7 H7 . . 118.6 ?
C8 C7 H7 . . 118.6 ?
C3 C8 C7 . . 119.4(2) ?
C3 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C12 C9 C6 . . 107.44(17) ?
C12 C9 C10 . . 109.1(2) ?
C6 C9 C10 . . 112.6(2) ?
C12 C9 C11 . . 112.0(2) ?
C6 C9 C11 . . 108.5(2) ?
C10 C9 C11 . . 107.2(2) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C13 C12 C17 . . 116.4(2) ?
C13 C12 C9 . . 124.6(2) ?
C17 C12 C9 . . 119.0(2) ?
C12 C13 C14 . . 121.5(2) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C15 C14 C13 . . 120.8(2) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 119.0(2) ?
C14 C15 O6 . . 116.6(2) ?
C16 C15 O6 . . 124.3(2) ?
C15 C16 C17 . . 119.3(2) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C16 C17 C12 . . 122.9(2) ?
C16 C17 H17 . . 118.6 ?
C12 C17 H17 . . 118.6 ?
O4 C18 O5 . . 125.5(2) ?
O4 C18 C19 . . 121.8(3) ?
O5 C18 C19 . . 112.7(3) ?
O6 C19 C18 . . 114.6(2) ?
O6 C19 H19A . . 108.6 ?
C18 C19 H19A . . 108.6 ?
O6 C19 H19B . . 108.6 ?
C18 C19 H19B . . 108.6 ?
H19A C19 H19B . . 107.6 ?
N1 C20 H20A . . 109.5 ?
N1 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
N1 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N1 C21 H21A . . 109.5 ?
N1 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N1 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.231(3) y
O2 C1 . 1.258(3) y
O3 C3 . 1.373(3) ?
O3 C2 . 1.420(3) ?
O4 C18 . 1.196(3) y
O5 C18 . 1.308(3) y
O5 H5 . 0.8206 ?
O6 C15 . 1.377(3) ?
O6 C19 . 1.419(3) ?
N1 C21 . 1.470(3) ?
N1 C20 . 1.472(3) ?
N1 H1A . 0.8997 ?
N1 H1B . 0.9003 ?
C1 C2 . 1.511(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C8 . 1.373(3) ?
C3 C4 . 1.380(3) ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.391(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.372(3) ?
C6 C9 . 1.534(3) ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C12 . 1.533(3) ?
C9 C10 . 1.534(3) ?
C9 C11 . 1.536(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.377(3) ?
C12 C17 . 1.382(3) ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.368(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.374(3) ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 C19 . 1.501(3) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 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 H5 O2 2_645 0.82 1.70 2.507(2) 167
N1 H1B O1 1_655 0.90 1.87 2.758(3) 169
N1 H1A O3 . 0.90 2.54 3.245(3) 136
N1 H1A O2 . 0.90 1.98 2.800(3) 151
C20 H20A O4 2_655 0.96 2.47 3.368(4) 155
C20 H20C O4 4_575 0.96 2.58 3.300(4) 132
C20 H20C O5 2_755 0.96 2.58 3.374(3) 140
C21 H21A O5 2_755 0.96 2.45 3.282(3) 145
C21 H21B O1 3_676 0.96 2.54 3.390(4) 148
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O3 C2 C1 . . . . -80.7(2) y
O1 C1 C2 O3 . . . . 170.0(2) y
O2 C1 C2 O3 . . . . -10.8(3) ?
C2 O3 C3 C8 . . . . 14.1(3) ?
C2 O3 C3 C4 . . . . -166.7(2) y
C8 C3 C4 C5 . . . . -0.3(4) ?
O3 C3 C4 C5 . . . . -179.5(2) ?
C3 C4 C5 C6 . . . . 0.8(4) ?
C4 C5 C6 C7 . . . . -0.8(4) ?
C4 C5 C6 C9 . . . . -179.3(2) ?
C5 C6 C7 C8 . . . . 0.3(4) ?
C9 C6 C7 C8 . . . . 178.8(2) ?
O3 C3 C8 C7 . . . . 178.9(2) ?
C4 C3 C8 C7 . . . . -0.2(4) ?
C6 C7 C8 C3 . . . . 0.2(4) ?
C7 C6 C9 C12 . . . . -120.9(2) ?
C5 C6 C9 C12 . . . . 57.5(3) ?
C7 C6 C9 C10 . . . . -0.8(3) ?
C5 C6 C9 C10 . . . . 177.7(2) ?
C7 C6 C9 C11 . . . . 117.7(3) ?
C5 C6 C9 C11 . . . . -63.8(3) ?
C6 C9 C12 C13 . . . . -113.2(3) ?
C10 C9 C12 C13 . . . . 124.4(2) ?
C11 C9 C12 C13 . . . . 5.8(3) ?
C6 C9 C12 C17 . . . . 63.4(3) ?
C10 C9 C12 C17 . . . . -59.0(3) ?
C11 C9 C12 C17 . . . . -177.5(2) ?
C17 C12 C13 C14 . . . . -1.9(3) ?
C9 C12 C13 C14 . . . . 174.8(2) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . 2.7(4) ?
C13 C14 C15 O6 . . . . -176.4(2) ?
C19 O6 C15 C14 . . . . -173.4(2) y
C19 O6 C15 C16 . . . . 7.6(3) ?
C14 C15 C16 C17 . . . . -3.2(3) ?
O6 C15 C16 C17 . . . . 175.8(2) ?
C15 C16 C17 C12 . . . . 1.2(4) ?
C13 C12 C17 C16 . . . . 1.4(3) ?
C9 C12 C17 C16 . . . . -175.6(2) ?
C15 O6 C19 C18 . . . . 69.4(3) y
O4 C18 C19 O6 . . . . -156.7(2) ?
O5 C18 C19 O6 . . . . 25.0(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654197
