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#$Date: 2025-01-24 08:20:56 +0200 (Fri, 24 Jan 2025) $
#$Revision: 297458 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/05/3000562.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_3000562
loop_
_publ_author_name
'Gogoi, Diptajyoti'
'Sasaki, Toshiyuki'
'Kalita, Nabadeep'
'Sethi, Tapaswini'
'Ichiyanagi, Kouhei'
'Nakane, Takanori'
'Kawamoto, Akihiro'
'Das, Dinabandhu'
'Kurisu, Genji'
'Thakuria, Ranjit'
_publ_section_title
;
 Tuning of a Hydrogen-Bonded Organic Framework by Liquid-Assisted
 Mechanosynthesis between Trans-Aconitic Acid and Isonicotinamide
;
_journal_name_full               'Chemistry A European Journal'
_journal_page_first              e202403427(1)
_journal_page_last               e202403427(10)
_journal_paper_doi               10.1002/chem.202403427
_journal_volume                  31
_journal_year                    2025
_chemical_formula_moiety         'C43 H44 N11 O20'
_chemical_formula_sum            'C43 H44 N11 O20'
_chemical_formula_weight         1034.89
_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   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                102.48(3)
_cell_angle_beta                 101.82(3)
_cell_angle_gamma                98.28(5)
_cell_formula_units_Z            1
_cell_length_a                   7.507(19)
_cell_length_b                   11.44(3)
_cell_length_c                   15.40(4)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      3.10
_cell_volume                     1239(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41141
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.482
_diffrn_reflns_theta_min         1.396
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             539
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.085
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1678P)²+0.9800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2709
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4200
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rt_ps59_taca_ina_1_2_thf_nitromethane_0m_a.cif
_cod_data_source_block           rt_ps59_taca_ina_1_2_thf_nitromethane_0m_a
_cod_depositor_comments
'Releasing structure 3000562 into public domain as published material.'
_cod_database_code               3000562
_shelx_shelxl_version_number     2016/6
_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   0.975
_shelx_estimated_absorpt_t_max   0.988
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.0073(4) 0.7646(2) 0.76802(18) 0.0395(6) Uani 1 1 d . . . . .
C2 C 0.9334(3) 0.6290(2) 0.75566(18) 0.0362(5) Uani 1 1 d . . . . .
C3 C 0.9046(4) 0.5919(2) 0.82979(18) 0.0396(6) Uani 1 1 d . . . . .
H3 H 0.932105 0.653395 0.883816 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8345(4) 0.4656(2) 0.83832(18) 0.0410(6) Uani 1 1 d . . . . .
C5 C 0.9054(4) 0.5504(2) 0.65819(18) 0.0411(6) Uani 1 1 d . . . . .
H5A H 1.023740 0.555920 0.641677 0.049 Uiso 1 1 calc R U . . .
H5B H 0.860725 0.465747 0.656254 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7672(4) 0.5905(2) 0.58851(17) 0.0382(6) Uani 1 1 d . . . . .
C7 C 0.2545(4) 0.3144(2) 0.85512(18) 0.0389(6) Uani 1 1 d . . . . .
C8 C 0.2311(4) 0.2847(2) 0.9360(2) 0.0469(7) Uani 1 1 d . . . . .
H8 H 0.256734 0.345011 0.990591 0.056 Uiso 1 1 calc R U . . .
C9 C 0.1683(4) 0.1619(3) 0.9333(2) 0.0491(7) Uani 1 1 d . . . . .
H9 H 0.151923 0.142599 0.987123 0.059 Uiso 1 1 calc R U . . .
C10 C 0.1546(5) 0.0999(3) 0.7782(2) 0.0551(8) Uani 1 1 d . . . . .
H10 H 0.130031 0.037726 0.724741 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2151(5) 0.2198(3) 0.7751(2) 0.0520(7) Uani 1 1 d . . . . .
H11 H 0.229121 0.236704 0.720175 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3200(4) 0.4451(2) 0.85030(19) 0.0422(6) Uani 1 1 d . . . . .
C13 C 0.5656(4) 0.9301(2) 0.81857(19) 0.0389(6) Uani 1 1 d . . . . .
C14 C 0.5841(5) 0.9472(3) 0.7332(2) 0.0568(8) Uani 1 1 d . . . . .
H14 H 0.554463 0.881076 0.681991 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6478(6) 1.0649(3) 0.7262(2) 0.0616(9) Uani 1 1 d . . . . .
H15 H 0.658683 1.075733 0.669195 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6781(5) 1.1475(3) 0.8806(2) 0.0512(7) Uani 1 1 d . . . . .
H16 H 0.710842 1.215311 0.930537 0.061 Uiso 1 1 calc R U . . .
C17 C 0.6146(4) 1.0333(2) 0.8943(2) 0.0471(7) Uani 1 1 d . . . . .
H17 H 0.604791 1.025594 0.952092 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4941(4) 0.8049(2) 0.83227(18) 0.0388(6) Uani 1 1 d . . . . .
C19 C 0.1203(4) 0.9157(3) 0.5009(2) 0.0574(7) Uani 0.5 1 d . . P A 1
N5 N 0.1203(4) 0.9157(3) 0.5009(2) 0.0574(7) Uani 0.5 1 d . . P A 2
C20 C -0.0592(5) 0.8839(3) 0.5047(3) 0.0661(9) Uani 1 1 d . . . . .
H20 H -0.103772 0.805098 0.507747 0.079 Uiso 1 1 calc R U . A 1
C21 C 0.1788(5) 1.0318(3) 0.4959(3) 0.0634(9) Uani 1 1 d . . . . .
H21 H 0.300560 1.056066 0.492763 0.076 Uiso 1 1 calc R U . A 1
C22 C 0.2575(9) 0.8181(5) 0.4980(4) 0.0976(15) Uani 1 1 d . . . . .
N1 N 0.3178(4) 0.5377(2) 0.92025(17) 0.0452(6) Uani 1 1 d . . . . .
N3 N 0.4958(4) 0.7069(2) 0.76603(19) 0.0505(6) Uani 1 1 d D . . . .
N2 N 0.1304(4) 0.0705(2) 0.85632(18) 0.0486(6) Uani 1 1 d . . . . .
N4 N 0.6940(4) 1.1634(2) 0.79826(19) 0.0510(6) Uani 1 1 d . . . . .
N6 N 0.2452(9) 0.7368(5) 0.5492(4) 0.137(2) Uani 1 1 d . . . . .
O1 O 0.9926(3) 0.83784(17) 0.84507(15) 0.0515(5) Uani 1 1 d . . . . .
O2 O 1.0738(3) 0.80046(19) 0.70973(15) 0.0577(6) Uani 1 1 d . . . . .
O3 O 0.7975(5) 0.4532(2) 0.91016(17) 0.0797(9) Uani 1 1 d . . . . .
O4 O 0.8202(4) 0.37291(17) 0.76831(15) 0.0589(6) Uani 1 1 d . . . . .
O5 O 0.6644(3) 0.6609(2) 0.60805(14) 0.0537(6) Uani 1 1 d . . . . .
O6 O 0.7698(4) 0.5409(2) 0.50216(14) 0.0615(6) Uani 1 1 d . . . . .
O7 O 0.3714(4) 0.46221(19) 0.78103(17) 0.0710(8) Uani 1 1 d . . . . .
O8 O 0.4365(3) 0.79751(18) 0.90181(15) 0.0556(6) Uani 1 1 d . . . . .
O9 O 0.3713(6) 0.7990(6) 0.4623(4) 0.197(3) Uani 1 1 d . . . . .
O10 O 0.5622(4) 0.6334(3) 0.38872(18) 0.0804(9) Uani 1 1 d D . . . .
H1C H 1.051(6) 0.916(4) 0.847(3) 0.078(12) Uiso 1 1 d . . . . .
H6A H 0.692(7) 0.578(5) 0.462(3) 0.094(15) Uiso 1 1 d . . . . .
H10B H 0.549(6) 0.604(4) 0.3244(9) 0.090(14) Uiso 1 1 d D . . . .
H10A H 0.501(7) 0.700(3) 0.404(4) 0.108(17) Uiso 1 1 d D . . . .
H4A H 0.770(7) 0.286(5) 0.783(4) 0.104(16) Uiso 1 1 d . . . . .
H1B H 0.353(4) 0.617(3) 0.913(2) 0.047(8) Uiso 1 1 d . . . . .
H3B H 0.455(5) 0.6224(16) 0.773(3) 0.064(10) Uiso 1 1 d D . . . .
H1A H 0.267(5) 0.529(3) 0.969(3) 0.060(10) Uiso 1 1 d . . . . .
H3A H 0.565(5) 0.698(4) 0.716(2) 0.081(12) 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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 '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
O2 C1 O1 124.0(3) . .
O2 C1 C2 121.0(2) . .
O1 C1 C2 115.0(2) . .
C3 C2 C1 118.0(2) . .
C3 C2 C5 127.7(3) . .
C1 C2 C5 114.3(2) . .
C2 C3 C4 129.7(2) . .
C2 C3 H3 115.1 . .
C4 C3 H3 115.1 . .
O3 C4 O4 122.9(3) . .
O3 C4 C3 119.3(2) . .
O4 C4 C3 117.8(3) . .
C6 C5 C2 111.9(3) . .
C6 C5 H5A 109.2 . .
C2 C5 H5A 109.2 . .
C6 C5 H5B 109.2 . .
C2 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
O5 C6 O6 122.6(3) . .
O5 C6 C5 124.8(3) . .
O6 C6 C5 112.6(3) . .
C8 C7 C11 118.2(3) . .
C8 C7 C12 123.0(2) . .
C11 C7 C12 118.8(3) . .
C7 C8 C9 118.7(3) . .
C7 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
N2 C9 C8 123.2(3) . .
N2 C9 H9 118.4 . .
C8 C9 H9 118.4 . .
N2 C10 C11 122.5(3) . .
N2 C10 H10 118.8 . .
C11 C10 H10 118.8 . .
C10 C11 C7 119.6(3) . .
C10 C11 H11 120.2 . .
C7 C11 H11 120.2 . .
O7 C12 N1 122.3(3) . .
O7 C12 C7 119.0(2) . .
N1 C12 C7 118.7(3) . .
C14 C13 C17 118.2(3) . .
C14 C13 C18 122.5(2) . .
C17 C13 C18 119.3(3) . .
C15 C14 C13 119.0(3) . .
C15 C14 H14 120.5 . .
C13 C14 H14 120.5 . .
N4 C15 C14 122.8(3) . .
N4 C15 H15 118.6 . .
C14 C15 H15 118.6 . .
N4 C16 C17 122.9(3) . .
N4 C16 H16 118.5 . .
C17 C16 H16 118.5 . .
C16 C17 C13 118.6(3) . .
C16 C17 H17 120.7 . .
C13 C17 H17 120.7 . .
O8 C18 N3 123.4(3) . .
O8 C18 C13 120.0(2) . .
N3 C18 C13 116.6(3) . .
C21 C19 C20 117.3(3) . .
C21 C19 C22 121.0(4) . .
C20 C19 C22 121.7(4) . .
C21 N5 C20 117.3(3) . .
C21 N5 C22 121.0(4) . .
C20 N5 C22 121.7(4) . .
N5 C20 C21 121.2(4) . 2_576
C19 C20 C21 121.2(4) . 2_576
C19 C20 H20 119.4 . .
C21 C20 H20 119.4 2_576 .
C19 C21 C20 121.5(4) . 2_576
C19 C21 H21 119.2 . .
C20 C21 H21 119.2 2_576 .
O9 C22 N6 106.0(7) . .
O9 C22 C19 135.4(6) . .
N6 C22 C19 118.5(5) . .
O9 C22 N5 135.4(6) . .
N6 C22 N5 118.5(5) . .
C12 N1 H1B 116(2) . .
C12 N1 H1A 124(2) . .
H1B N1 H1A 119(3) . .
C18 N3 H3B 119(2) . .
C18 N3 H3A 131(3) . .
H3B N3 H3A 107(3) . .
C9 N2 C10 117.8(3) . .
C16 N4 C15 118.5(3) . .
C1 O1 H1C 107(3) . .
C4 O4 H4A 111(3) . .
C6 O6 H6A 109(3) . .
H10B O10 H10A 113(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.228(4) .
C1 O1 1.332(4) .
C1 C2 1.527(5) .
C2 C3 1.347(5) .
C2 C5 1.529(5) .
C3 C4 1.507(5) .
C3 H3 0.9300 .
C4 O3 1.226(4) .
C4 O4 1.313(4) .
C5 C6 1.527(4) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O5 1.227(4) .
C6 O6 1.334(4) .
C7 C8 1.398(5) .
C7 C11 1.400(5) .
C7 C12 1.527(5) .
C8 C9 1.405(5) .
C8 H8 0.9300 .
C9 N2 1.348(5) .
C9 H9 0.9300 .
C10 N2 1.356(5) .
C10 C11 1.396(5) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 O7 1.250(4) .
C12 N1 1.343(4) .
C13 C14 1.401(5) .
C13 C17 1.412(5) .
C13 C18 1.530(5) .
C14 C15 1.398(5) .
C14 H14 0.9300 .
C15 N4 1.345(5) .
C15 H15 0.9300 .
C16 N4 1.345(5) .
C16 C17 1.399(5) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 O8 1.249(4) .
C18 N3 1.347(4) .
C19 C21 1.361(6) .
C19 C20 1.361(6) .
C19 C22 1.624(8) .
N5 C21 1.361(6) .
N5 C20 1.361(6) .
N5 C22 1.624(8) .
C20 C21 1.409(6) 2_576
C20 H20 0.9300 .
C21 H21 0.9300 .
C22 O9 1.129(7) .
C22 N6 1.348(7) .
N1 H1B 0.95(4) .
N1 H1A 0.92(4) .
N3 H3B 1.008(10) .
N3 H3A 1.004(10) .
O1 H1C 0.93(5) .
O4 H4A 1.09(5) .
O6 H6A 0.97(5) .
O10 H10B 0.954(10) .
O10 H10A 0.954(10) .
