#------------------------------------------------------------------------------
#$Date: 2022-11-08 10:07:21 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105997.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_8105997
loop_
_publ_author_name
'Chang, Xin-Hong'
_publ_section_title
;
 Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate ---
 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1253
_journal_page_last               1254
_journal_paper_doi               10.1515/ncrs-2019-0377
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C13 H10 N, C4 H2 O3, C4 H3 O3'
_chemical_formula_sum            'C21 H15 N O6'
_chemical_formula_weight         377.34
_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
_cell_angle_alpha                102.581(4)
_cell_angle_beta                 92.929(4)
_cell_angle_gamma                102.573(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3591(4)
_cell_length_b                   9.4371(5)
_cell_length_c                   10.1106(5)
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    288.7(3)
_cell_measurement_theta_max      27.0170
_cell_measurement_theta_min      4.1410
_cell_volume                     846.09(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      288.7(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -5.00  76.00   1.00    7.00    --   12.26  38.00 -60.00   81
  2  ω     38.00  79.00   1.00    7.00    --   12.26  57.00  30.00   41
  3  ω      6.00  34.00   1.00    7.00    --   12.26  57.00 120.00   28
  4  ω     -6.00  79.00   1.00    7.00    --   12.26  77.00 150.00   85
  5  ω     -1.00  67.00   1.00    7.00    --   12.26  57.00   0.00   68
  6  ω    -38.00  55.00   1.00    7.00    --  -11.32  77.00-120.00   93
  7  ω    -16.00  51.00   1.00    7.00    --   12.26 -99.00 120.00   67
  8  ω     21.00  51.00   1.00    7.00    --   12.26 -99.00  30.00   30
  9  ω    -15.00  51.00   1.00    7.00    --   12.26 -99.00-180.00   66
 10  ω    -55.00  10.00   1.00    7.00    --   12.26 -57.00   0.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0261274000
_diffrn_orient_matrix_UB_12      0.0499931000
_diffrn_orient_matrix_UB_13      0.0507327000
_diffrn_orient_matrix_UB_21      0.0297747000
_diffrn_orient_matrix_UB_22      0.0597047000
_diffrn_orient_matrix_UB_23      -0.0301409000
_diffrn_orient_matrix_UB_31      -0.0672709000
_diffrn_orient_matrix_UB_32      -0.0145730000
_diffrn_orient_matrix_UB_33      -0.0417174000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10752
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.483
_diffrn_reflns_theta_min         3.209
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0452
_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)+(0.0420P)²+0.3930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2499
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0377_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105997
_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   0.983
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.06
_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.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C14(H14), C19(H19)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O4(H4A), O5(H5)
;
_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 1.482
_oxdiff_exptl_absorpt_empirical_full_min 0.651
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
N1 N 0.41853(16) 0.38719(18) 0.79478(15) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.4915 0.3939 0.7463 0.035 Uiso 1 1 calc R . . . .
C1 C 0.4759(2) 0.6554(2) 0.8570(2) 0.0345(5) Uani 1 1 d . . . . .
H1A H 0.5537 0.6609 0.8032 0.041 Uiso 1 1 calc R . . . .
C2 C 0.4447(2) 0.7815(2) 0.9303(2) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.5022 0.8739 0.9262 0.050 Uiso 1 1 calc R . . . .
C3 C 0.3272(3) 0.7760(2) 1.0126(2) 0.0433(6) Uani 1 1 d . . . . .
H3 H 0.3092 0.8643 1.0627 0.052 Uiso 1 1 calc R . . . .
C4 C 0.2404(2) 0.6430(2) 1.0191(2) 0.0385(5) Uani 1 1 d . . . . .
H4 H 0.1628 0.6408 1.0731 0.046 Uiso 1 1 calc R . . . .
C5 C 0.2671(2) 0.5063(2) 0.94356(18) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.1825(2) 0.3661(2) 0.94405(19) 0.0326(5) Uani 1 1 d . . . . .
H6 H 0.1010 0.3589 0.9933 0.039 Uiso 1 1 calc R . . . .
C7 C 0.2163(2) 0.2362(2) 0.87274(19) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.1334(2) 0.0897(2) 0.8707(2) 0.0430(5) Uani 1 1 d . . . . .
H8 H 0.0504 0.0780 0.9177 0.052 Uiso 1 1 calc R . . . .
C9 C 0.1739(3) -0.0322(3) 0.8013(2) 0.0479(6) Uani 1 1 d . . . . .
H9 H 0.1182 -0.1270 0.8002 0.057 Uiso 1 1 calc R . . . .
C10 C 0.3009(3) -0.0164(2) 0.7303(2) 0.0451(6) Uani 1 1 d . . . . .
H10 H 0.3284 -0.1015 0.6846 0.054 Uiso 1 1 calc R . . . .
C11 C 0.3831(2) 0.1201(2) 0.7276(2) 0.0371(5) Uani 1 1 d . . . . .
H11 H 0.4662 0.1287 0.6804 0.045 Uiso 1 1 calc R . . . .
C12 C 0.3410(2) 0.2495(2) 0.79748(18) 0.0287(4) Uani 1 1 d . . . . .
C13 C 0.3882(2) 0.5152(2) 0.86381(18) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.60291(14) 0.34549(17) 0.44697(14) 0.0433(4) Uani 1 1 d . . . . .
O2 O 0.66247(14) 0.43920(16) 0.67028(14) 0.0384(4) Uani 1 1 d . . . . .
O3 O 0.92840(15) 0.57414(19) 0.76347(13) 0.0462(4) Uani 1 1 d . . . . .
H3A H 0.8400 0.5432 0.7666 0.069 Uiso 1 1 calc GR . . . .
C14 C 0.89348(19) 0.4251(2) 0.39358(18) 0.0268(4) Uani 1 1 d . . . . .
H14 H 0.8218 0.3749 0.3217 0.032 Uiso 1 1 calc R . . . .
C15 C 0.85271(19) 0.45881(19) 0.52453(17) 0.0236(4) Uani 1 1 d . . . . .
C16 C 0.6944(2) 0.4114(2) 0.54846(19) 0.0282(4) Uani 1 1 d . . . . .
C17 C 0.9612(2) 0.5355(2) 0.63228(17) 0.0264(4) Uani 1 1 d . . . . .
O4 O -0.13293(16) 0.18322(16) 0.67900(16) 0.0454(4) Uani 1 1 d . . . . .
H4A H -0.2104 0.1351 0.6972 0.068 Uiso 1 1 calc GR . . . .
O5 O 0.33512(14) 0.26655(15) 0.47314(15) 0.0378(4) Uani 1 1 d . . . . .
H5 H 0.4230 0.2864 0.4628 0.057 Uiso 1 1 calc GR . . . .
O6 O 0.33634(17) 0.05419(18) 0.32518(18) 0.0578(5) Uani 1 1 d . . . . .
C18 C 0.13156(19) 0.0637(2) 0.45407(18) 0.0267(4) Uani 1 1 d . . . . .
C19 C 0.0605(2) 0.1523(2) 0.54319(19) 0.0284(4) Uani 1 1 d . . . . .
H19 H 0.1009 0.2545 0.5717 0.034 Uiso 1 1 calc R . . . .
C20 C -0.0696(2) 0.0910(2) 0.59015(19) 0.0290(4) Uani 1 1 d . . . . .
C21 C 0.2764(2) 0.1284(2) 0.4111(2) 0.0320(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 0.0033 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
C12 N1 H1 118.1 . .
C12 N1 C13 123.87(16) . .
C13 N1 H1 118.1 . .
C2 C1 H1A 120.5 . .
C2 C1 C13 118.90(19) . .
C13 C1 H1A 120.5 . .
C1 C2 H2 119.2 . .
C1 C2 C3 121.6(2) . .
C3 C2 H2 119.2 . .
C2 C3 H3 119.8 . .
C4 C3 C2 120.5(2) . .
C4 C3 H3 119.8 . .
C3 C4 H4 119.7 . .
C3 C4 C5 120.5(2) . .
C5 C4 H4 119.7 . .
C6 C5 C4 123.88(18) . .
C6 C5 C13 118.37(17) . .
C13 C5 C4 117.75(19) . .
C5 C6 H6 119.2 . .
C5 C6 C7 121.64(18) . .
C7 C6 H6 119.2 . .
C6 C7 C8 123.76(19) . .
C6 C7 C12 118.36(18) . .
C12 C7 C8 117.88(19) . .
C7 C8 H8 119.6 . .
C9 C8 C7 120.8(2) . .
C9 C8 H8 119.6 . .
C8 C9 H9 119.8 . .
C8 C9 C10 120.4(2) . .
C10 C9 H9 119.8 . .
C9 C10 H10 119.3 . .
C11 C10 C9 121.4(2) . .
C11 C10 H10 119.3 . .
C10 C11 H11 120.4 . .
C10 C11 C12 119.2(2) . .
C12 C11 H11 120.4 . .
N1 C12 C7 118.83(17) . .
N1 C12 C11 120.83(18) . .
C11 C12 C7 120.34(18) . .
N1 C13 C1 120.43(17) . .
N1 C13 C5 118.86(17) . .
C1 C13 C5 120.71(18) . .
C17 O3 H3A 109.5 . .
C15 C14 H14 119.4 . .
C17 C14 H14 119.4 2_766 .
C17 C14 C15 121.30(16) 2_766 .
C14 C15 C16 119.58(16) . .
C14 C15 C17 119.05(16) . .
C17 C15 C16 121.37(16) . .
O1 C16 O2 124.45(17) . .
O1 C16 C15 117.90(16) . .
O2 C16 C15 117.64(16) . .
O3 C17 C14 118.24(16) . 2_766
O3 C17 C15 122.11(16) . .
C14 C17 C15 119.65(16) 2_766 .
C20 O4 H4A 109.5 . .
C21 O5 H5 109.5 . .
C19 C18 C20 119.49(17) . 2_556
C19 C18 C21 120.81(17) . .
C20 C18 C21 119.60(17) 2_556 .
C18 C19 H19 119.5 . .
C20 C19 C18 121.01(17) . .
C20 C19 H19 119.5 . .
O4 C20 C18 122.20(17) . 2_556
O4 C20 C19 118.31(17) . .
C19 C20 C18 119.49(17) . 2_556
O5 C21 C18 115.05(17) . .
O6 C21 O5 123.17(18) . .
O6 C21 C18 121.76(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1 0.8600 .
N1 C12 1.350(2) .
N1 C13 1.353(2) .
C1 H1A 0.9300 .
C1 C2 1.356(3) .
C1 C13 1.415(3) .
C2 H2 0.9300 .
C2 C3 1.411(3) .
C3 H3 0.9300 .
C3 C4 1.355(3) .
C4 H4 0.9300 .
C4 C5 1.429(3) .
C5 C6 1.388(3) .
C5 C13 1.422(3) .
C6 H6 0.9300 .
C6 C7 1.390(3) .
C7 C8 1.425(3) .
C7 C12 1.423(3) .
C8 H8 0.9300 .
C8 C9 1.351(3) .
C9 H9 0.9300 .
C9 C10 1.416(3) .
C10 H10 0.9300 .
C10 C11 1.356(3) .
C11 H11 0.9300 .
C11 C12 1.417(3) .
O1 C16 1.254(2) .
O2 C16 1.267(2) .
O3 H3A 0.8200 .
O3 C17 1.366(2) .
C14 H14 0.9300 .
C14 C15 1.386(2) .
C14 C17 1.384(2) 2_766
C15 C16 1.500(2) .
C15 C17 1.402(2) .
C17 C14 1.384(2) 2_766
O4 H4A 0.8200 .
O4 C20 1.362(2) .
O5 H5 0.8200 .
O5 C21 1.301(2) .
O6 C21 1.231(2) .
C18 C19 1.389(3) .
C18 C20 1.410(3) 2_556
C18 C21 1.488(3) .
C19 H19 0.9300 .
C19 C20 1.384(3) .
C20 C18 1.410(3) 2_556
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 1.82 2.6670(19) 168.9 .
O3 H3A O2 0.82 1.84 2.5616(19) 146.3 .
O4 H4A O6 0.82 1.87 2.596(2) 146.2 2_556
O5 H5 O1 0.82 1.68 2.4994(18) 174.2 .
