#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/52/4515256.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_4515256
loop_
_publ_author_name
'Lou, Xiaobing'
'Geng, Fushan'
'Hu, Bei'
'Li, Chao'
'Shen, Ming'
'Hu, Bingwen'
_publ_section_title
;
 Reversible High-Voltage N-Redox Chemistry in Metal--Organic Frameworks
 for High-Rate Anion-Intercalation Batteries
;
_journal_issue                   1
_journal_name_full               'ACS Applied Energy Materials'
_journal_page_first              413
_journal_paper_doi               10.1021/acsaem.8b01428
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         '2(C10 H8 N O2)'
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35
_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     dual
_audit_creation_date             2018-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                92.633(2)
_cell_angle_beta                 106.665(3)
_cell_angle_gamma                97.402(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0016(3)
_cell_length_b                   10.0412(2)
_cell_length_c                   15.4610(6)
_cell_measurement_reflns_used    7702
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1950
_cell_measurement_theta_min      4.4550
_cell_volume                     1322.56(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -28.00  15.00   1.00    1.00    --    0.00 -38.00-180.00   43
  2  ω     61.00  89.00   1.00    1.00    --    0.00  38.00-120.00   28
  3  ω    -89.00 -37.00   1.00    1.00    --    0.00 -38.00-180.00   52
  4  ω    -17.00  21.00   1.00    1.00    --    0.00 -57.00 120.00   38
  5  ω    -85.00 -42.00   1.00    1.00    --    0.00 -19.00-150.00   43
  6  ω    -20.00  17.00   1.00    1.00    --    0.00 -19.00-150.00   37
  7  ω    -79.00 -27.00   1.00    1.00    --    0.00 -57.00 120.00   52
  8  ω      7.00 128.00   1.00    2.00    --   95.80 -82.00 -30.00  121
  9  ω     76.00 183.00   1.00    2.00    --   95.80  30.00-150.00  107
 10  ω      9.00  70.00   1.00    2.00    --   95.80 -77.00 -90.00   61
 11  ω    134.00 178.00   1.00    2.00    --   95.80  30.00-180.00   44
 12  ω      7.00  99.00   1.00    2.00    --   95.80 -61.00 -30.00   92
 13  ω     29.00  72.00   1.00    2.00    --   95.80 -82.00-150.00   43
 14  ω     75.00 116.00   1.00    2.00    --   95.80 -82.00-150.00   41
 15  ω     19.00 126.00   1.00    2.00    --   95.80 -82.00 120.00  107
 16  ω      6.00 116.00   1.00    2.00    --   95.80 -45.00  90.00  110
 17  ω     15.00  41.00   1.00    2.00    --   95.80 -77.00 150.00   26
 18  ω    131.00 176.00   1.00    2.00    --   95.80  30.00 -90.00   45
 19  ω     67.00  98.00   1.00    2.00    --   95.80 -77.00 150.00   31
 20  ω      6.00  69.00   1.00    2.00    --   95.80 -61.00 -90.00   63
 21  ω     90.00 124.00   1.00    2.00    --   95.80 -82.00   0.00   34
 22  ω     41.00  91.00   1.00    2.00    --   95.80 -30.00   0.00   50
 23  ω     85.00 111.00   1.00    2.00    --   95.80  30.00 -90.00   26
 24  ω     72.00  97.00   1.00    2.00    --   95.80 -77.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1772540000
_diffrn_orient_matrix_UB_12      0.0188912000
_diffrn_orient_matrix_UB_13      0.0110842000
_diffrn_orient_matrix_UB_21      0.0344015000
_diffrn_orient_matrix_UB_22      -0.0014378000
_diffrn_orient_matrix_UB_23      0.1034457000
_diffrn_orient_matrix_UB_31      -0.0056061000
_diffrn_orient_matrix_UB_32      -0.1541467000
_diffrn_orient_matrix_UB_33      -0.0087845000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12374
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.875
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4646
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0789
_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)+(0.1372P)²+0.4427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2322
_refine_ls_wR_factor_ref         0.2417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3849
_reflns_number_total             4646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ae8b01428_si_003.cif
_cod_data_source_block           exp_271
_cod_database_code               4515256
_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_max   0.818
_shelx_estimated_absorpt_t_min   0.796
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C3 \\sim C4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2A), C3(H3), C4(H4), C5(H5), C8(H8), N2(H2B), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C18(H18)
4.b Tetrahedral OH refined with riding coordinates:
 O2(H2), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.809
_oxdiff_exptl_absorpt_empirical_full_min 0.582
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
O1 O 0.2491(3) 0.6773(2) 0.46873(16) 0.0781(6) Uani 1 1 d . .
O2 O 0.4388(3) 0.6445(2) 0.40738(17) 0.0815(7) Uani 1 1 d . .
H2 H 0.390431 0.567658 0.396558 0.122 Uiso 1 1 calc R .
N1 N 0.3889(3) 1.13674(19) 0.62693(15) 0.0562(6) Uani 1 1 d . .
H1 H 0.391734 1.222360 0.624301 0.067 Uiso 1 1 calc R .
C1 C 0.3696(3) 0.9641(3) 0.72968(17) 0.0626(7) Uani 1 1 d . .
H1A H 0.440179 0.918668 0.710897 0.075 Uiso 1 1 calc R .
C2 C 0.3052(4) 0.9139(3) 0.79604(18) 0.0728(8) Uani 1 1 d . .
H2A H 0.331514 0.834528 0.820968 0.087 Uiso 1 1 calc R .
C3 C 0.2019(4) 0.9835(4) 0.8243(2) 0.0876(10) Uani 1 1 d . U
H3 H 0.157567 0.949964 0.867724 0.105 Uiso 1 1 calc R .
C4 C 0.1653(4) 1.0989(4) 0.7894(2) 0.0845(9) Uani 1 1 d . U
H4 H 0.099080 1.146637 0.810731 0.101 Uiso 1 1 calc R .
C5 C 0.2243(3) 1.1472(3) 0.72301(18) 0.0591(6) Uani 1 1 d . .
H5 H 0.194357 1.225629 0.697993 0.071 Uiso 1 1 calc R .
C6 C 0.3286(3) 1.0809(2) 0.69205(15) 0.0495(6) Uani 1 1 d . .
C7 C 0.4456(3) 1.0698(2) 0.56521(14) 0.0447(5) Uani 1 1 d . .
C8 C 0.3885(3) 0.9344(2) 0.53364(14) 0.0480(5) Uani 1 1 d . .
H8 H 0.312235 0.889326 0.555930 0.058 Uiso 1 1 calc R .
C9 C 0.4395(3) 0.8641(2) 0.47101(15) 0.0477(5) Uani 1 1 d . .
C10 C 0.3661(3) 0.7204(3) 0.44651(16) 0.0558(6) Uani 1 1 d . .
O3 O 1.0711(2) 0.1855(2) 0.09212(16) 0.0736(6) Uani 1 1 d . .
H3A H 1.115038 0.119197 0.104300 0.110 Uiso 1 1 calc R .
O4 O 1.2543(2) 0.23109(18) 0.02449(13) 0.0623(5) Uani 1 1 d . .
N2 N 0.7668(2) 0.5576(2) 0.07757(14) 0.0536(5) Uani 1 1 d . .
H2B H 0.702847 0.608267 0.048518 0.064 Uiso 1 1 calc R .
C11 C 0.8603(4) 0.5041(3) 0.23655(19) 0.0724(8) Uani 1 1 d . .
H11 H 0.964127 0.523376 0.236518 0.087 Uiso 1 1 calc R .
C12 C 0.8286(5) 0.4694(5) 0.3134(2) 0.0963(12) Uani 1 1 d . .
H12 H 0.909750 0.467462 0.366295 0.116 Uiso 1 1 calc R .
C13 C 0.6725(6) 0.4364(4) 0.3126(3) 0.1012(14) Uani 1 1 d . .
H13 H 0.649175 0.411696 0.365049 0.121 Uiso 1 1 calc R .
C14 C 0.5591(5) 0.4402(4) 0.2379(3) 0.0932(12) Uani 1 1 d . .
H14 H 0.455653 0.418099 0.238189 0.112 Uiso 1 1 calc R .
C15 C 0.5893(4) 0.4764(3) 0.1585(2) 0.0670(7) Uani 1 1 d . .
H15 H 0.506660 0.476756 0.106131 0.080 Uiso 1 1 calc R .
C16 C 0.7403(3) 0.5116(2) 0.15705(16) 0.0503(6) Uani 1 1 d . .
C17 C 0.8834(2) 0.5310(2) 0.04085(13) 0.0392(5) Uani 1 1 d . .
C18 C 0.9574(2) 0.4175(2) 0.05980(15) 0.0426(5) Uani 1 1 d . .
H18 H 0.928610 0.360509 0.099903 0.051 Uiso 1 1 calc R .
C19 C 1.0720(2) 0.3852(2) 0.02173(14) 0.0407(5) Uani 1 1 d . .
C20 C 1.1430(3) 0.2621(2) 0.04683(15) 0.0467(5) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 O2 H2 109.5 . .
C6 N1 H1 116.4 . .
C6 N1 C7 127.19(19) . .
C7 N1 H1 116.4 . .
C2 C1 H1A 119.9 . .
C6 C1 H1A 119.9 . .
C6 C1 C2 120.1(3) . .
C1 C2 H2A 120.3 . .
C3 C2 C1 119.4(3) . .
C3 C2 H2A 120.3 . .
C2 C3 H3 119.7 . .
C4 C3 C2 120.5(3) . .
C4 C3 H3 119.7 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.7(3) . .
C5 C4 H4 119.7 . .
C4 C5 H5 119.4 . .
C4 C5 C6 121.1(3) . .
C6 C5 H5 119.4 . .
N1 C6 C5 118.7(2) . .
C1 C6 N1 123.1(2) . .
C1 C6 C5 118.2(2) . .
N1 C7 C8 121.5(2) . .
N1 C7 C9 121.79(19) . 2_676
C8 C7 C9 116.7(2) . 2_676
C7 C8 H8 118.2 . .
C9 C8 C7 123.6(2) . .
C9 C8 H8 118.2 . .
C7 C9 C10 124.5(2) 2_676 .
C8 C9 C7 119.7(2) . 2_676
C8 C9 C10 115.7(2) . .
O1 C10 O2 123.4(2) . .
O1 C10 C9 120.2(2) . .
O2 C10 C9 116.3(2) . .
C20 O3 H3A 109.5 . .
C16 N2 H2B 116.3 . .
C17 N2 H2B 116.3 . .
C17 N2 C16 127.45(18) . .
C12 C11 H11 119.3 . .
C12 C11 C16 121.4(3) . .
C16 C11 H11 119.3 . .
C11 C12 H12 120.4 . .
C11 C12 C13 119.3(3) . .
C13 C12 H12 120.4 . .
C12 C13 H13 120.1 . .
C14 C13 C12 119.9(3) . .
C14 C13 H13 120.1 . .
C13 C14 H14 119.2 . .
C13 C14 C15 121.7(4) . .
C15 C14 H14 119.2 . .
C14 C15 H15 119.9 . .
C16 C15 C14 120.1(3) . .
C16 C15 H15 119.9 . .
C11 C16 N2 123.5(2) . .
C15 C16 N2 118.8(2) . .
C15 C16 C11 117.6(2) . .
N2 C17 C18 121.69(18) . .
N2 C17 C19 121.21(18) . 2_765
C18 C17 C19 117.03(18) . 2_765
C17 C18 H18 118.4 . .
C19 C18 C17 123.25(19) . .
C19 C18 H18 118.4 . .
C17 C19 C20 121.58(18) 2_765 .
C18 C19 C17 119.71(18) . 2_765
C18 C19 C20 118.70(19) . .
O3 C20 C19 113.47(18) . .
O4 C20 O3 122.30(19) . .
O4 C20 C19 124.16(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.232(3) .
O2 H2 0.8200 .
O2 C10 1.300(3) .
N1 H1 0.8600 .
N1 C6 1.382(3) .
N1 C7 1.390(3) .
C1 H1A 0.9300 .
C1 C2 1.399(4) .
C1 C6 1.379(4) .
C2 H2A 0.9300 .
C2 C3 1.384(5) .
C3 H3 0.9300 .
C3 C4 1.340(6) .
C4 H4 0.9300 .
C4 C5 1.365(4) .
C5 H5 0.9300 .
C5 C6 1.394(3) .
C7 C8 1.402(3) .
C7 C9 1.419(3) 2_676
C8 H8 0.9300 .
C8 C9 1.386(3) .
C9 C10 1.491(3) .
O3 H3A 0.8200 .
O3 C20 1.297(3) .
O4 C20 1.219(3) .
N2 H2B 0.8600 .
N2 C16 1.404(3) .
N2 C17 1.377(3) .
C11 H11 0.9300 .
C11 C12 1.349(5) .
C11 C16 1.397(4) .
C12 H12 0.9300 .
C12 C13 1.399(6) .
C13 H13 0.9300 .
C13 C14 1.310(6) .
C14 H14 0.9300 .
C14 C15 1.386(4) .
C15 H15 0.9300 .
C15 C16 1.366(4) .
C17 C18 1.394(3) .
C17 C19 1.420(3) 2_765
C18 H18 0.9300 .
C18 C19 1.391(3) .
C19 C20 1.481(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345665
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
1 0.224 -0.562 0.276 576.4 10.2
