#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/17/2221783.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_2221783
loop_
_publ_author_name
'Derikvand, Zohreh'
'Aghabozorg, Hossein'
'Attar Gharamaleki, Jafar'
_publ_section_title
;
 Acridinium 3,5-dicarboxybenzoate monohydrate
;
_journal_coeditor_code           PV2154
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1173
_journal_paper_doi               10.1107/S1600536809015529
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H10 N +, C9 H5 O6 -, H2 O'
_chemical_formula_moiety         'C13 H10 N +, C9 H5 O6 -, H2 O'
_chemical_formula_sum            'C22 H17 N O7'
_chemical_formula_weight         407.37
_chemical_name_systematic
;
Acridinium 3,5-dicarboxybenzoate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.6870(10)
_cell_angle_beta                 101.4240(10)
_cell_angle_gamma                103.3100(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8554(4)
_cell_length_b                   9.6930(6)
_cell_length_c                   14.8916(10)
_cell_measurement_reflns_used    5147
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.26
_cell_volume                     901.62(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000 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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9138
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0457
_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)+(0.08P)²+0.36P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                3659
_reflns_number_total             4275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2154.cif
_cod_data_source_block           I
_cod_database_code               2221783
_cod_database_fobs_code          2221783
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.53402(13) 0.57945(10) 0.27673(6) 0.0210(2) Uani d . 1 . .
O O2 0.84684(14) 0.54218(10) 0.30488(6) 0.0236(2) Uani d . 1 . .
O O3 0.76596(15) 0.03275(10) -0.06853(6) 0.0239(2) Uani d . 1 . .
H H3O 0.8501 -0.0268 -0.0766 0.029 Uiso d R 1 . .
O O4 0.96967(16) 0.12545(11) 0.08194(7) 0.0283(2) Uani d . 1 . .
O O5 0.07764(15) 0.36662(11) -0.05679(7) 0.0247(2) Uani d . 1 . .
H H5O -0.0207 0.3674 -0.1061 0.030 Uiso d R 1 . .
O O6 0.16639(16) 0.20983(12) -0.16763(7) 0.0287(2) Uani d . 1 . .
O O7 0.16191(15) 0.62966(12) 0.21813(7) 0.0295(2) Uani d . 1 . .
H H7B 0.2751 0.6054 0.2375 0.044 Uiso d R 1 . .
H H7C 0.0765 0.5958 0.2499 0.044 Uiso d R 1 . .
N N1 0.68310(16) 0.81261(11) 0.43083(7) 0.0179(2) Uani d . 1 . .
H H1N 0.6431 0.7352 0.3794 0.022 Uiso calc R 1 . .
C C1 0.8239(2) 0.88639(15) 0.69373(9) 0.0240(3) Uani d . 1 . .
H H1A 0.8669 0.9668 0.7510 0.029 Uiso calc R 1 . .
C C2 0.7957(2) 0.74436(16) 0.69839(9) 0.0253(3) Uani d . 1 . .
H H2A 0.8134 0.7262 0.7590 0.030 Uiso calc R 1 . .
C C3 0.7401(2) 0.62373(15) 0.61357(10) 0.0241(3) Uani d . 1 . .
H H3A 0.7253 0.5261 0.6184 0.029 Uiso calc R 1 . .
C C4 0.70732(19) 0.64520(14) 0.52498(9) 0.0211(3) Uani d . 1 . .
H H4A 0.6729 0.5637 0.4688 0.025 Uiso calc R 1 . .
C C4A 0.72531(18) 0.79041(13) 0.51809(9) 0.0181(2) Uani d . 1 . .
C C5 0.6491(2) 0.96360(15) 0.32571(9) 0.0225(3) Uani d . 1 . .
H H5A 0.6004 0.8784 0.2711 0.027 Uiso calc R 1 . .
C C6 0.6712(2) 1.10214(16) 0.31508(10) 0.0264(3) Uani d . 1 . .
H H6A 0.6369 1.1125 0.2525 0.032 Uiso calc R 1 . .
C C7 0.7447(2) 1.23140(15) 0.39604(11) 0.0266(3) Uani d . 1 . .
H H7A 0.7607 1.3267 0.3869 0.032 Uiso calc R 1 . .
C C8 0.7923(2) 1.21908(14) 0.48666(10) 0.0246(3) Uani d . 1 . .
H H8A 0.8408 1.3058 0.5402 0.029 Uiso calc R 1 . .
C C8A 0.76947(18) 1.07638(13) 0.50154(9) 0.0197(3) Uani d . 1 . .
C C9 0.81271(19) 1.05643(14) 0.59263(9) 0.0214(3) Uani d . 1 . .
H H9A 0.8587 1.1402 0.6481 0.026 Uiso calc R 1 . .
C C9A 0.78877(18) 0.91388(14) 0.60267(9) 0.0197(3) Uani d . 1 . .
C C10A 0.69968(19) 0.94890(14) 0.41914(9) 0.0188(2) Uani d . 1 . .
C C10 0.60515(18) 0.40594(13) 0.15426(8) 0.0175(2) Uani d . 1 . .
C C11 0.73036(19) 0.31547(13) 0.13153(9) 0.0186(2) Uani d . 1 . .
H H11A 0.8505 0.3220 0.1787 0.022 Uiso calc R 1 . .
C C12 0.68132(19) 0.21555(13) 0.04031(9) 0.0180(2) Uani d . 1 . .
C C13 0.50674(19) 0.20648(13) -0.02982(9) 0.0185(2) Uani d . 1 . .
H H13A 0.4746 0.1400 -0.0925 0.022 Uiso calc R 1 . .
C C14 0.37953(18) 0.29568(13) -0.00735(8) 0.0179(2) Uani d . 1 . .
C C15 0.42717(18) 0.39407(13) 0.08446(9) 0.0180(2) Uani d . 1 . .
H H15A 0.3385 0.4532 0.0996 0.022 Uiso calc R 1 . .
C C16 0.66843(19) 0.51724(13) 0.25273(8) 0.0182(2) Uani d . 1 . .
C C17 0.8191(2) 0.12108(14) 0.01994(9) 0.0197(2) Uani d . 1 . .
C C18 0.19722(19) 0.28509(14) -0.08559(9) 0.0197(2) 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'
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
C17 O3 H3O . . 111.8 ?
C18 O5 H5O . . 111.9 ?
H7B O7 H7C . . 105.4 ?
C4A N1 C10A . . 122.85(11) ?
C4A N1 H1N . . 118.6 ?
C10A N1 H1N . . 118.6 ?
C2 C1 C9A . . 119.94(12) ?
C2 C1 H1A . . 120.0 ?
C9A C1 H1A . . 120.0 ?
C1 C2 C3 . . 120.64(12) ?
C1 C2 H2A . . 119.7 ?
C3 C2 H2A . . 119.7 ?
C4 C3 C2 . . 121.31(12) ?
C4 C3 H3A . . 119.3 ?
C2 C3 H3A . . 119.3 ?
C3 C4 C4A . . 119.08(12) ?
C3 C4 H4A . . 120.5 ?
C4A C4 H4A . . 120.5 ?
N1 C4A C4 . . 119.84(11) ?
N1 C4A C9A . . 119.77(11) ?
C4 C4A C9A . . 120.39(11) ?
C6 C5 C10A . . 119.08(12) ?
C6 C5 H5A . . 120.5 ?
C10A C5 H5A . . 120.5 ?
C5 C6 C7 . . 121.30(13) ?
C5 C6 H6A . . 119.3 ?
C7 C6 H6A . . 119.3 ?
C8 C7 C6 . . 120.37(12) ?
C8 C7 H7A . . 119.8 ?
C6 C7 H7A . . 119.8 ?
C7 C8 C8A . . 120.42(12) ?
C7 C8 H8A . . 119.8 ?
C8A C8 H8A . . 119.8 ?
C9 C8A C10A . . 118.83(11) ?
C9 C8A C8 . . 123.08(12) ?
C10A C8A C8 . . 118.09(12) ?
C8A C9 C9A . . 120.49(11) ?
C8A C9 H9A . . 119.8 ?
C9A C9 H9A . . 119.8 ?
C9 C9A C4A . . 118.55(11) ?
C9 C9A C1 . . 122.95(12) ?
C4A C9A C1 . . 118.50(12) ?
N1 C10A C5 . . 119.81(11) ?
N1 C10A C8A . . 119.46(11) ?
C5 C10A C8A . . 120.73(12) ?
C11 C10 C15 . . 119.08(11) ?
C11 C10 C16 . . 119.12(10) ?
C15 C10 C16 . . 121.77(11) ?
C10 C11 C12 . . 120.76(11) ?
C10 C11 H11A . . 119.6 ?
C12 C11 H11A . . 119.6 ?
C13 C12 C11 . . 120.05(11) ?
C13 C12 C17 . . 121.31(11) ?
C11 C12 C17 . . 118.63(11) ?
C12 C13 C14 . . 119.52(11) ?
C12 C13 H13A . . 120.2 ?
C14 C13 H13A . . 120.2 ?
C13 C14 C15 . . 120.32(11) ?
C13 C14 C18 . . 117.62(11) ?
C15 C14 C18 . . 122.02(11) ?
C14 C15 C10 . . 120.23(11) ?
C14 C15 H15A . . 119.9 ?
C10 C15 H15A . . 119.9 ?
O2 C16 O1 . . 124.40(11) ?
O2 C16 C10 . . 118.44(11) ?
O1 C16 C10 . . 117.17(10) ?
O4 C17 O3 . . 123.27(11) ?
O4 C17 C12 . . 121.71(11) ?
O3 C17 C12 . . 115.01(10) ?
O6 C18 O5 . . 124.18(11) ?
O6 C18 C14 . . 122.11(11) ?
O5 C18 C14 . . 113.70(11) ?
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 C16 . 1.2747(15) ?
O2 C16 . 1.2474(15) ?
O3 C17 . 1.3167(15) ?
O3 H3O . 0.9102 ?
O4 C17 . 1.2261(16) ?
O5 C18 . 1.3258(15) ?
O5 H5O . 0.8953 ?
O6 C18 . 1.2143(16) ?
O7 H7B . 0.8764 ?
O7 H7C . 0.8773 ?
N1 C4A . 1.3529(16) ?
N1 C10A . 1.3550(16) ?
N1 H1N . 0.8800 ?
C1 C2 . 1.366(2) ?
C1 C9A . 1.4280(18) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.4188(19) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.3668(18) ?
C3 H3A . 0.9500 ?
C4 C4A . 1.4144(17) ?
C4 H4A . 0.9500 ?
C4A C9A . 1.4275(17) ?
C5 C6 . 1.3667(19) ?
C5 C10A . 1.4148(17) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.425(2) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.364(2) ?
C7 H7A . 0.9500 ?
C8 C8A . 1.4303(18) ?
C8 H8A . 0.9500 ?
C8A C9 . 1.3988(18) ?
C8A C10A . 1.4280(17) ?
C9 C9A . 1.4006(18) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.3934(16) ?
C10 C15 . 1.3995(17) ?
C10 C16 . 1.5120(16) ?
C11 C12 . 1.3938(16) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.3942(17) ?
C12 C17 . 1.4844(16) ?
C13 C14 . 1.3950(16) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.3957(17) ?
C14 C18 . 1.4958(17) ?
C15 H15A . 0.9500 ?
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
N1 H1N O1 . 0.88 1.76 2.6403(14) 174 y
O3 H3O O4 2_755 0.91 1.73 2.6370(15) 174 y
O5 H5O O7 2_565 0.90 1.77 2.6412(14) 165 y
O7 H7B O1 . 0.88 1.85 2.7197(14) 172 y
O7 H7C O2 1_455 0.88 1.94 2.7989(15) 167 y
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
C9A C1 C2 C3 . . . . 2.7(2) ?
C1 C2 C3 C4 . . . . -1.9(2) ?
C2 C3 C4 C4A . . . . -1.30(19) ?
C10A N1 C4A C4 . . . . -179.17(11) ?
C10A N1 C4A C9A . . . . 0.52(18) ?
C3 C4 C4A N1 . . . . -176.65(11) ?
C3 C4 C4A C9A . . . . 3.66(18) ?
C10A C5 C6 C7 . . . . 0.2(2) ?
C5 C6 C7 C8 . . . . -0.9(2) ?
C6 C7 C8 C8A . . . . 0.2(2) ?
C7 C8 C8A C9 . . . . -179.04(12) ?
C7 C8 C8A C10A . . . . 1.11(18) ?
C10A C8A C9 C9A . . . . 0.28(18) ?
C8 C8A C9 C9A . . . . -179.57(11) ?
C8A C9 C9A C4A . . . . 1.79(18) ?
C8A C9 C9A C1 . . . . -177.87(11) ?
N1 C4A C9A C9 . . . . -2.23(17) ?
C4 C4A C9A C9 . . . . 177.46(11) ?
N1 C4A C9A C1 . . . . 177.44(11) ?
C4 C4A C9A C1 . . . . -2.87(18) ?
C2 C1 C9A C9 . . . . 179.34(12) ?
C2 C1 C9A C4A . . . . -0.32(19) ?
C4A N1 C10A C5 . . . . -178.76(11) ?
C4A N1 C10A C8A . . . . 1.62(18) ?
C6 C5 C10A N1 . . . . -178.51(11) ?
C6 C5 C10A C8A . . . . 1.10(19) ?
C9 C8A C10A N1 . . . . -2.01(17) ?
C8 C8A C10A N1 . . . . 177.85(10) ?
C9 C8A C10A C5 . . . . 178.37(11) ?
C8 C8A C10A C5 . . . . -1.77(18) ?
C15 C10 C11 C12 . . . . 0.76(18) ?
C16 C10 C11 C12 . . . . -177.54(11) ?
C10 C11 C12 C13 . . . . 0.80(19) ?
C10 C11 C12 C17 . . . . -179.65(11) ?
C11 C12 C13 C14 . . . . -1.38(18) ?
C17 C12 C13 C14 . . . . 179.08(11) ?
C12 C13 C14 C15 . . . . 0.41(18) ?
C12 C13 C14 C18 . . . . 178.41(11) ?
C13 C14 C15 C10 . . . . 1.15(18) ?
C18 C14 C15 C10 . . . . -176.75(11) ?
C11 C10 C15 C14 . . . . -1.73(18) ?
C16 C10 C15 C14 . . . . 176.53(11) ?
C11 C10 C16 O2 . . . . 11.75(17) ?
C15 C10 C16 O2 . . . . -166.50(11) ?
C11 C10 C16 O1 . . . . -168.22(11) ?
C15 C10 C16 O1 . . . . 13.52(17) ?
C13 C12 C17 O4 . . . . -177.96(12) ?
C11 C12 C17 O4 . . . . 2.49(19) ?
C13 C12 C17 O3 . . . . 1.45(17) ?
C11 C12 C17 O3 . . . . -178.10(11) ?
C13 C14 C18 O6 . . . . -4.89(18) ?
C15 C14 C18 O6 . . . . 173.07(12) ?
C13 C14 C18 O5 . . . . 176.13(11) ?
C15 C14 C18 O5 . . . . -5.91(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655771
