#------------------------------------------------------------------------------
#$Date: 2020-06-20 07:52:49 +0300 (Sat, 20 Jun 2020) $
#$Revision: 253289 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243442.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_2243442
loop_
_publ_author_name
'Tiouabi, Mustapha'
'Tabacchi, Raphaël'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 The crystal structure, Hirshfeld surface analysis and energy frameworks
 of 2-[2-(methoxycarbonyl)-3,6-bis(methoxymethoxy)phenyl]acetic acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1101
_journal_page_last               1106
_journal_paper_doi               10.1107/S2056989020007987
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C14 H18 O8'
_chemical_formula_moiety         'C14 H18 O8'
_chemical_formula_sum            'C14 H18 O8'
_chemical_formula_weight         314.28
_chemical_name_systematic
;
2-[2-(Methoxycarbonyl)-3,6-bis(methoxymethoxy)phenyl]acetic acid
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                112.534(14)
_cell_angle_beta                 94.744(15)
_cell_angle_gamma                97.999(16)
_cell_formula_units_Z            2
_cell_length_a                   8.5628(12)
_cell_length_b                   9.6623(13)
_cell_length_c                   9.9767(12)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.15
_cell_volume                     746.6(2)
_computing_cell_refinement
;
CELL in IPDS-I (Stoe & Cie, 2004)
;
_computing_data_collection
;
EXPOSE in IPDS-I (Stoe & Cie, 2004)
;
_computing_data_reduction
;
INTEGRATE in IPDS-I (Stoe & Cie, 2004)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020) and
publcif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate'
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device       '1 circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 1'
_diffrn_measurement_method       'φ rotation'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6011
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         2.322
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS; Spek, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.228
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
(SHELXL2018/3; Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.832
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0446
_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)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                1557
_reflns_number_total             2752
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2033sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        746.60(19)
_cod_database_code               2243442
_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   0.966
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.25754(19) 0.8960(2) 0.1239(2) 0.0457(5) Uani d 1 . .
O O2 0.30589(19) 0.94409(18) 0.3608(2) 0.0427(5) Uani d 1 . .
O O3 -0.08148(17) 0.86702(16) 0.21564(19) 0.0354(4) Uani d 1 . .
O O4 -0.36196(18) 0.82093(18) 0.1605(2) 0.0411(5) Uani d 1 . .
O O5 0.12039(17) 0.34010(16) 0.18992(18) 0.0313(4) Uani d 1 . .
O O6 -0.07328(18) 0.23819(17) 0.29737(19) 0.0357(4) Uani d 1 . .
O O7 0.35707(18) 0.58696(18) 0.45712(19) 0.0373(4) Uani d 1 . .
O O8 0.52484(19) 0.4650(2) 0.3133(2) 0.0449(5) Uani d 1 . .
H H8 0.548084 0.441888 0.384533 0.067 Uiso calc 1 . .
C C1 0.1715(2) 0.5912(2) 0.2067(2) 0.0255(5) Uani d 1 . .
C C2 0.1204(2) 0.7231(2) 0.2130(2) 0.0255(5) Uani d 1 . .
C C3 -0.0431(2) 0.7295(2) 0.2044(3) 0.0266(5) Uani d 1 . .
C C4 -0.1531(2) 0.6025(2) 0.1876(3) 0.0290(5) Uani d 1 . .
H H4 -0.263625 0.606043 0.179939 0.035 Uiso calc 1 . .
C C5 -0.1034(2) 0.4714(2) 0.1817(3) 0.0292(5) Uani d 1 . .
H H5 -0.179938 0.384882 0.170246 0.035 Uiso calc 1 . .
C C6 0.0580(2) 0.4643(2) 0.1925(2) 0.0262(5) Uani d 1 . .
C C7 0.2333(2) 0.8614(2) 0.2243(3) 0.0284(5) Uani d 1 . .
C C8 0.4160(3) 1.0825(3) 0.3806(3) 0.0494(7) Uani d 1 . .
H H8A 0.495875 1.056174 0.314572 0.074 Uiso calc 1 . .
H H8B 0.469429 1.131775 0.482449 0.074 Uiso calc 1 . .
H H8C 0.356664 1.152557 0.357997 0.074 Uiso calc 1 . .
C C9 -0.2285(3) 0.8986(3) 0.2679(3) 0.0376(6) Uani d 1 . .
H H9A -0.238127 0.869474 0.352219 0.045 Uiso calc 1 . .
H H9B -0.226769 1.009573 0.303253 0.045 Uiso calc 1 . .
C C10 -0.3713(3) 0.8721(3) 0.0443(3) 0.0509(7) Uani d 1 . .
H H10A -0.362356 0.983164 0.085357 0.076 Uiso calc 1 . .
H H10B -0.473812 0.824240 -0.019781 0.076 Uiso calc 1 . .
H H10C -0.284222 0.844062 -0.012623 0.076 Uiso calc 1 . .
C C11 0.0113(3) 0.2090(2) 0.1794(3) 0.0314(5) Uani d 1 . .
H H11A -0.065027 0.172092 0.087538 0.038 Uiso calc 1 . .
H H11B 0.071162 0.126917 0.174037 0.038 Uiso calc 1 . .
C C12 0.0227(3) 0.2754(3) 0.4335(3) 0.0487(7) Uani d 1 . .
H H12A 0.078802 0.191711 0.426820 0.073 Uiso calc 1 . .
H H12B -0.044987 0.291178 0.510676 0.073 Uiso calc 1 . .
H H12C 0.100661 0.368863 0.457137 0.073 Uiso calc 1 . .
C C13 0.3446(2) 0.5742(3) 0.2107(3) 0.0313(6) Uani d 1 . .
H H13A 0.356492 0.490502 0.118404 0.038 Uiso calc 1 . .
H H13B 0.409856 0.669321 0.215295 0.038 Uiso calc 1 . .
C C14 0.4080(2) 0.5412(2) 0.3378(3) 0.0305(5) Uani 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'
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
C7 O2 C8 . . 115.27(19) ?
C3 O3 C9 . . 116.23(16) ?
C9 O4 C10 . . 113.21(19) ?
C6 O5 C11 . . 117.44(16) ?
C11 O6 C12 . . 113.99(18) ?
C14 O8 H8 . . 109.5 ?
C2 C1 C6 . . 119.14(18) ?
C2 C1 C13 . . 123.33(18) ?
C6 C1 C13 . . 117.51(18) ?
C1 C2 C3 . . 120.27(18) ?
C1 C2 C7 . . 122.31(18) ?
C3 C2 C7 . . 117.40(18) ?
O3 C3 C4 . . 124.46(18) ?
O3 C3 C2 . . 115.83(17) ?
C4 C3 C2 . . 119.71(18) ?
C5 C4 C3 . . 120.44(19) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.48(18) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
O5 C6 C5 . . 125.22(17) ?
O5 C6 C1 . . 114.84(17) ?
C5 C6 C1 . . 119.94(19) ?
O1 C7 O2 . . 122.7(2) ?
O1 C7 C2 . . 125.0(2) ?
O2 C7 C2 . . 112.25(19) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O4 C9 O3 . . 113.0(2) ?
O4 C9 H9A . . 109.0 ?
O3 C9 H9A . . 109.0 ?
O4 C9 H9B . . 109.0 ?
O3 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
O4 C10 H10A . . 109.5 ?
O4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
O4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O6 C11 O5 . . 112.89(17) ?
O6 C11 H11A . . 109.0 ?
O5 C11 H11A . . 109.0 ?
O6 C11 H11B . . 109.0 ?
O5 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
O6 C12 H12A . . 109.5 ?
O6 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O6 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C1 . . 113.74(19) ?
C14 C13 H13A . . 108.8 ?
C1 C13 H13A . . 108.8 ?
C14 C13 H13B . . 108.8 ?
C1 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
O7 C14 O8 . . 123.2(2) ?
O7 C14 C13 . . 122.6(2) ?
O8 C14 C13 . . 114.1(2) ?
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 C7 . 1.196(3) ?
O2 C7 . 1.329(3) ?
O2 C8 . 1.461(3) ?
O3 C3 . 1.379(2) ?
O3 C9 . 1.429(3) ?
O4 C9 . 1.400(3) ?
O4 C10 . 1.425(3) ?
O5 C6 . 1.372(2) ?
O5 C11 . 1.429(2) ?
O6 C11 . 1.390(3) ?
O6 C12 . 1.417(3) ?
O7 C14 . 1.240(3) ?
O8 C14 . 1.308(3) ?
O8 H8 . 0.8400 ?
C1 C2 . 1.386(3) ?
C1 C6 . 1.408(3) ?
C1 C13 . 1.513(3) ?
C2 C3 . 1.406(3) ?
C2 C7 . 1.496(3) ?
C3 C4 . 1.383(3) ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.391(3) ?
C5 H5 . 0.9500 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.499(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
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
_geom_hbond_publ_flag
C4 H4 O4 . 0.95 2.41 3.022(3) 122 no
O8 H8 O7 2_666 0.84 1.85 2.676(2) 168 yes
C9 H9B O6 1_565 0.99 2.43 3.256(3) 140 yes
C11 H11A O1 2_565 0.99 2.38 3.366(3) 175 yes
C13 H13B O4 1_655 0.99 2.50 3.421(3) 155 yes
C12 H12B Cg 2_566 0.98 2.66 3.451(3) 138 yes
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
C6 C1 C2 C3 . . . . -0.3(3) ?
C13 C1 C2 C3 . . . . 178.2(2) ?
C6 C1 C2 C7 . . . . -178.5(2) ?
C13 C1 C2 C7 . . . . 0.0(3) ?
C9 O3 C3 C4 . . . . 24.5(3) ?
C9 O3 C3 C2 . . . . -154.8(2) ?
C1 C2 C3 O3 . . . . 178.31(19) ?
C7 C2 C3 O3 . . . . -3.4(3) ?
C1 C2 C3 C4 . . . . -1.0(3) ?
C7 C2 C3 C4 . . . . 177.3(2) ?
O3 C3 C4 C5 . . . . -178.0(2) ?
C2 C3 C4 C5 . . . . 1.2(3) ?
C3 C4 C5 C6 . . . . -0.1(3) ?
C11 O5 C6 C5 . . . . -1.9(3) ?
C11 O5 C6 C1 . . . . 178.44(19) ?
C4 C5 C6 O5 . . . . 179.1(2) ?
C4 C5 C6 C1 . . . . -1.2(3) ?
C2 C1 C6 O5 . . . . -178.9(2) ?
C13 C1 C6 O5 . . . . 2.6(3) ?
C2 C1 C6 C5 . . . . 1.4(3) ?
C13 C1 C6 C5 . . . . -177.2(2) ?
C8 O2 C7 O1 . . . . 1.1(3) ?
C8 O2 C7 C2 . . . . -178.97(19) ?
C1 C2 C7 O1 . . . . 99.6(3) ?
C3 C2 C7 O1 . . . . -78.6(3) ?
C1 C2 C7 O2 . . . . -80.3(3) ?
C3 C2 C7 O2 . . . . 101.5(2) ?
C10 O4 C9 O3 . . . . -67.6(2) ?
C3 O3 C9 O4 . . . . -77.8(2) ?
C12 O6 C11 O5 . . . . -65.5(2) ?
C6 O5 C11 O6 . . . . -61.3(2) ?
C2 C1 C13 C14 . . . . 119.8(2) ?
C6 C1 C13 C14 . . . . -61.7(3) ?
C1 C13 C14 O7 . . . . -29.8(3) ?
C1 C13 C14 O8 . . . . 152.52(19) ?

_cod_database_fobs_code 2243442
