#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229077.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_2229077
loop_
_publ_author_name
'Derikvand, Zohreh'
'Olmstead, Marilyn M.'
'Attar Gharamaleki, Jafar'
_publ_section_title
;
 Acridinium 6-carboxypyridine-2-carboxylate monohydrate
;
_journal_coeditor_code           HG2777
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o416
_journal_paper_doi               10.1107/S1600536810053791
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H10 N +, C7 H4 N O4 -, H2 O'
_chemical_formula_moiety         'C13 H10 N +, C7 H4 N O4 -, H2 O'
_chemical_formula_sum            'C20 H16 N2 O5'
_chemical_formula_weight         364.35
_chemical_name_common            '[acridineH+][pydcH-] monohydrate'
_chemical_name_systematic
;
Acridinium 6-carboxypyridine-2-carboxylate 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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.266(3)
_cell_angle_beta                 93.851(2)
_cell_angle_gamma                97.766(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4842(3)
_cell_length_b                   8.6850(3)
_cell_length_c                   13.0305(4)
_cell_measurement_reflns_used    7626
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      32.9
_cell_measurement_theta_min      2.6
_cell_volume                     822.16(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       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  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0125
_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       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11632
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0346
_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)+(0.0621P)²+0.1884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                4034
_reflns_number_total             4403
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2777.cif
_cod_data_source_block           I
_cod_database_code               2229077
_cod_database_fobs_code          2229077
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 0.49045(9) 0.63220(8) 0.25575(5) 0.02109(15) Uani d . 1 . .
O O2 0.19185(9) 0.63670(8) 0.23357(5) 0.01783(14) Uani d . 1 . .
O O3 0.62172(10) 0.08319(8) -0.08226(5) 0.02271(16) Uani d . 1 . .
O O4 0.75469(9) 0.23901(8) 0.06409(6) 0.02201(15) Uani d . 1 . .
H H4A 0.735(2) 0.320(2) 0.1097(13) 0.043(4) Uiso d . 1 . .
O O5 0.81245(10) 0.49602(9) 0.22739(6) 0.02321(16) Uani d . 1 . .
H H5A 0.721(2) 0.544(2) 0.2252(13) 0.044(4) Uiso d . 1 . .
H H5B 0.907(2) 0.560(2) 0.2244(13) 0.043(4) Uiso d . 1 . .
N N1 0.22761(10) 0.86086(8) 0.39668(6) 0.01351(15) Uani d . 1 . .
H H1 0.215(2) 0.771(2) 0.3318(14) 0.049(5) Uiso d . 1 . .
N N2 0.46280(10) 0.38054(8) 0.09346(5) 0.01356(15) Uani d . 1 . .
C C1 0.29254(11) 0.83725(10) 0.49119(6) 0.01346(16) Uani d . 1 . .
C C2 0.33756(12) 0.68689(11) 0.50193(7) 0.01783(18) Uani d . 1 . .
H H2 0.3209(19) 0.6010(17) 0.4401(11) 0.029(3) Uiso d . 1 . .
C C3 0.40456(13) 0.66579(12) 0.59791(8) 0.02161(19) Uani d . 1 . .
H H3 0.432(2) 0.5632(18) 0.6068(11) 0.034(4) Uiso d . 1 . .
C C4 0.43460(13) 0.79225(13) 0.68579(8) 0.0226(2) Uani d . 1 . .
H H4 0.486(2) 0.7719(18) 0.7514(12) 0.034(4) Uiso d . 1 . .
C C5 0.39282(12) 0.93759(12) 0.67742(7) 0.01935(18) Uani d . 1 . .
H H5 0.418(2) 1.0241(17) 0.7378(11) 0.031(4) Uiso d . 1 . .
C C6 0.31603(11) 0.96397(10) 0.57969(6) 0.01448(16) Uani d . 1 . .
C C7 0.26325(11) 1.10795(10) 0.56689(7) 0.01559(17) Uani d . 1 . .
H H7 0.2804(19) 1.1941(17) 0.6252(11) 0.028(3) Uiso d . 1 . .
C C8 0.19056(11) 1.12820(10) 0.46937(7) 0.01433(17) Uani d . 1 . .
C C9 0.13152(12) 1.27198(11) 0.45221(8) 0.01948(18) Uani d . 1 . .
H H9 0.139(2) 1.3590(17) 0.5148(11) 0.031(3) Uiso d . 1 . .
C C10 0.06669(13) 1.28604(12) 0.35436(9) 0.0227(2) Uani d . 1 . .
H H10 0.026(2) 1.3839(18) 0.3435(12) 0.037(4) Uiso d . 1 . .
C C11 0.05946(13) 1.15875(12) 0.26824(8) 0.02219(19) Uani d . 1 . .
H H11 0.016(2) 1.1712(18) 0.1989(12) 0.037(4) Uiso d . 1 . .
C C12 0.11412(12) 1.01882(11) 0.28081(7) 0.01838(18) Uani d . 1 . .
H H12 0.1125(19) 0.9325(17) 0.2221(11) 0.028(3) Uiso d . 1 . .
C C13 0.17760(11) 1.00027(10) 0.38252(6) 0.01340(16) Uani d . 1 . .
C C14 0.31558(11) 0.44843(9) 0.11517(6) 0.01310(16) Uani d . 1 . .
C C15 0.14892(12) 0.39585(11) 0.05742(7) 0.01748(17) Uani d . 1 . .
H H15 0.0454(18) 0.4460(16) 0.0776(10) 0.025(3) Uiso d . 1 . .
C C16 0.13303(13) 0.26913(12) -0.02620(7) 0.0224(2) Uani d . 1 . .
H H16 0.015(2) 0.2304(19) -0.0658(12) 0.039(4) Uiso d . 1 . .
C C17 0.28452(13) 0.19891(11) -0.04975(7) 0.02011(19) Uani d . 1 . .
H H17 0.280(2) 0.1079(17) -0.1077(11) 0.032(4) Uiso d . 1 . .
C C18 0.44547(11) 0.25928(10) 0.01274(6) 0.01459(16) Uani d . 1 . .
C C19 0.33787(12) 0.58364(10) 0.20896(6) 0.01463(16) Uani d . 1 . .
C C20 0.61355(12) 0.18562(10) -0.00691(7) 0.01689(17) 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
C20 O4 H4A . . 112.1(11) ?
H5A O5 H5B . . 109.3(16) ?
C1 N1 C13 . . 122.44(7) ?
C1 N1 H1 . . 120.2(10) ?
C13 N1 H1 . . 117.3(10) ?
C18 N2 C14 . . 117.75(7) ?
N1 C1 C2 . . 119.91(8) ?
N1 C1 C6 . . 119.81(8) ?
C2 C1 C6 . . 120.28(8) ?
C3 C2 C1 . . 119.03(9) ?
C3 C2 H2 . . 121.8(8) ?
C1 C2 H2 . . 119.2(8) ?
C2 C3 C4 . . 121.31(9) ?
C2 C3 H3 . . 119.9(9) ?
C4 C3 H3 . . 118.8(9) ?
C5 C4 C3 . . 120.73(8) ?
C5 C4 H4 . . 121.3(9) ?
C3 C4 H4 . . 118.0(9) ?
C4 C5 C6 . . 120.05(9) ?
C4 C5 H5 . . 119.8(9) ?
C6 C5 H5 . . 120.1(9) ?
C7 C6 C1 . . 118.53(8) ?
C7 C6 C5 . . 122.96(8) ?
C1 C6 C5 . . 118.52(8) ?
C6 C7 C8 . . 120.73(8) ?
C6 C7 H7 . . 119.2(9) ?
C8 C7 H7 . . 120.0(9) ?
C7 C8 C13 . . 118.48(8) ?
C7 C8 C9 . . 123.10(8) ?
C13 C8 C9 . . 118.42(8) ?
C10 C9 C8 . . 120.32(9) ?
C10 C9 H9 . . 122.8(8) ?
C8 C9 H9 . . 116.9(8) ?
C9 C10 C11 . . 120.43(9) ?
C9 C10 H10 . . 119.8(9) ?
C11 C10 H10 . . 119.7(9) ?
C12 C11 C10 . . 121.37(9) ?
C12 C11 H11 . . 119.0(9) ?
C10 C11 H11 . . 119.6(9) ?
C11 C12 C13 . . 119.08(9) ?
C11 C12 H12 . . 121.8(8) ?
C13 C12 H12 . . 119.1(8) ?
N1 C13 C12 . . 119.76(8) ?
N1 C13 C8 . . 119.91(7) ?
C12 C13 C8 . . 120.32(8) ?
N2 C14 C15 . . 122.24(8) ?
N2 C14 C19 . . 116.69(7) ?
C15 C14 C19 . . 121.05(7) ?
C14 C15 C16 . . 119.29(8) ?
C14 C15 H15 . . 119.3(8) ?
C16 C15 H15 . . 121.4(8) ?
C17 C16 C15 . . 118.93(8) ?
C17 C16 H16 . . 121.7(9) ?
C15 C16 H16 . . 119.3(9) ?
C16 C17 C18 . . 117.69(8) ?
C16 C17 H17 . . 122.0(9) ?
C18 C17 H17 . . 120.3(9) ?
N2 C18 C17 . . 124.10(8) ?
N2 C18 C20 . . 115.58(7) ?
C17 C18 C20 . . 120.31(8) ?
O1 C19 O2 . . 125.44(8) ?
O1 C19 C14 . . 119.23(8) ?
O2 C19 C14 . . 115.33(7) ?
O3 C20 O4 . . 121.35(8) ?
O3 C20 C18 . . 122.73(8) ?
O4 C20 C18 . . 115.92(7) ?
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 C19 . 1.2403(11) ?
O2 C19 . 1.2806(10) ?
O3 C20 . 1.2126(11) ?
O4 C20 . 1.3305(11) ?
O4 H4A . 0.869(17) ?
O5 H5A . 0.849(18) ?
O5 H5B . 0.845(18) ?
N1 C1 . 1.3533(11) ?
N1 C13 . 1.3538(11) ?
N1 H1 . 1.031(17) ?
N2 C18 . 1.3350(11) ?
N2 C14 . 1.3415(11) ?
C1 C2 . 1.4199(12) ?
C1 C6 . 1.4283(11) ?
C2 C3 . 1.3680(13) ?
C2 H2 . 0.984(14) ?
C3 C4 . 1.4208(15) ?
C3 H3 . 0.966(15) ?
C4 C5 . 1.3617(14) ?
C4 H4 . 0.969(15) ?
C5 C6 . 1.4303(12) ?
C5 H5 . 0.975(14) ?
C6 C7 . 1.3952(12) ?
C7 C8 . 1.3980(12) ?
C7 H7 . 0.955(14) ?
C8 C13 . 1.4256(11) ?
C8 C9 . 1.4282(12) ?
C9 C10 . 1.3655(14) ?
C9 H9 . 1.002(14) ?
C10 C11 . 1.4204(15) ?
C10 H10 . 0.972(16) ?
C11 C12 . 1.3665(13) ?
C11 H11 . 0.970(16) ?
C12 C13 . 1.4215(12) ?
C12 H12 . 0.969(14) ?
C14 C15 . 1.3885(12) ?
C14 C19 . 1.5194(11) ?
C15 C16 . 1.3901(12) ?
C15 H15 . 0.968(14) ?
C16 C17 . 1.3850(13) ?
C16 H16 . 0.977(16) ?
C17 C18 . 1.3908(12) ?
C17 H17 . 0.987(15) ?
C18 C20 . 1.5032(12) ?
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
O4 H4A O5 . 0.869(17) 1.958(17) 2.7604(10) 152.9(16)
O4 H4A N2 . 0.869(17) 2.182(17) 2.6646(10) 114.6(14)
O5 H5A O1 . 0.849(18) 2.016(18) 2.8421(10) 164.0(16)
O5 H5B O2 1_655 0.845(18) 2.134(18) 2.9255(10) 155.8(16)
N1 H1 O2 . 1.031(17) 1.555(18) 2.5859(9) 178.6(16)
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
C13 N1 C1 C2 . . . . 178.05(7) ?
C13 N1 C1 C6 . . . . -2.15(12) ?
N1 C1 C2 C3 . . . . 179.41(8) ?
C6 C1 C2 C3 . . . . -0.39(13) ?
C1 C2 C3 C4 . . . . -1.84(13) ?
C2 C3 C4 C5 . . . . 1.74(14) ?
C3 C4 C5 C6 . . . . 0.66(14) ?
N1 C1 C6 C7 . . . . 2.80(12) ?
C2 C1 C6 C7 . . . . -177.40(8) ?
N1 C1 C6 C5 . . . . -177.12(7) ?
C2 C1 C6 C5 . . . . 2.68(12) ?
C4 C5 C6 C7 . . . . 177.28(8) ?
C4 C5 C6 C1 . . . . -2.80(13) ?
C1 C6 C7 C8 . . . . -0.59(12) ?
C5 C6 C7 C8 . . . . 179.32(8) ?
C6 C7 C8 C13 . . . . -2.20(12) ?
C6 C7 C8 C9 . . . . 178.91(8) ?
C7 C8 C9 C10 . . . . 178.03(8) ?
C13 C8 C9 C10 . . . . -0.87(13) ?
C8 C9 C10 C11 . . . . -0.86(14) ?
C9 C10 C11 C12 . . . . 0.97(14) ?
C10 C11 C12 C13 . . . . 0.68(14) ?
C1 N1 C13 C12 . . . . 178.61(7) ?
C1 N1 C13 C8 . . . . -0.74(12) ?
C11 C12 C13 N1 . . . . 178.23(8) ?
C11 C12 C13 C8 . . . . -2.42(13) ?
C7 C8 C13 N1 . . . . 2.91(12) ?
C9 C8 C13 N1 . . . . -178.14(7) ?
C7 C8 C13 C12 . . . . -176.43(8) ?
C9 C8 C13 C12 . . . . 2.51(12) ?
C18 N2 C14 C15 . . . . 0.51(12) ?
C18 N2 C14 C19 . . . . 178.61(7) ?
N2 C14 C15 C16 . . . . -0.32(14) ?
C19 C14 C15 C16 . . . . -178.35(8) ?
C14 C15 C16 C17 . . . . -0.15(15) ?
C15 C16 C17 C18 . . . . 0.39(15) ?
C14 N2 C18 C17 . . . . -0.24(13) ?
C14 N2 C18 C20 . . . . -178.89(7) ?
C16 C17 C18 N2 . . . . -0.21(15) ?
C16 C17 C18 C20 . . . . 178.38(9) ?
N2 C14 C19 O1 . . . . 5.15(12) ?
C15 C14 C19 O1 . . . . -176.72(8) ?
N2 C14 C19 O2 . . . . -173.96(7) ?
C15 C14 C19 O2 . . . . 4.17(12) ?
N2 C18 C20 O3 . . . . -173.96(8) ?
C17 C18 C20 O3 . . . . 7.33(14) ?
N2 C18 C20 O4 . . . . 6.37(11) ?
C17 C18 C20 O4 . . . . -172.34(8) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656466
