Crystal structure of 1H-indole-5-carboxylic acid – 4,4′-bipyridine (2/1), C14H11N2O2
Linxin, Deng; Xinya, Kuang; Huarong, Yang; Song, Li; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 191–192; doi:10.1515/ncrs-2017-0084

data_8105585
_publ_section_title
;
 Crystal structure of 1H-indole-5-carboxylic acid --
 4,4&#x2032;-bipyridine (2/1), C14H11N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              191
_journal_page_last               192
_journal_paper_doi               10.1515/ncrs-2017-0084
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         '2(C9 H7 N O2), C10 H8 N2'
_chemical_formula_sum            'C28 H22 N4 O4'
_chemical_formula_weight         478.50
_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                78.200(6)
_cell_angle_beta                 83.007(6)
_cell_angle_gamma                85.035(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8749(6)
_cell_length_b                   9.6746(6)
_cell_length_c                   16.0818(12)
_cell_measurement_reflns_used    1750
_cell_measurement_temperature    295.42(10)
_cell_measurement_theta_max      25.5870
_cell_measurement_theta_min      3.0240
_cell_volume                     1188.00(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      295.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -32.00  32.00   1.00    5.00    --   15.49 -57.00 -60.00   64
  2  \w    -19.00  23.00   1.00    5.00    --  -16.12 -99.00-150.00   42
  3  \w    -45.00  31.00   1.00    5.00    --   15.49 -57.00-180.00   76
  4  \w    -51.00 -16.00   1.00    5.00    --   15.49 -77.00 -60.00   35
  5  \w    -16.00  23.00   1.00    5.00    --  -16.12 -99.00  90.00   39
  6  \w    -11.00  81.00   1.00    5.00    --   15.49  77.00  60.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0283270000
_diffrn_orient_matrix_UB_12      -0.0688424000
_diffrn_orient_matrix_UB_13      0.0203133000
_diffrn_orient_matrix_UB_21      0.0240930000
_diffrn_orient_matrix_UB_22      -0.0183291000
_diffrn_orient_matrix_UB_23      -0.0405063000
_diffrn_orient_matrix_UB_31      0.0829769000
_diffrn_orient_matrix_UB_32      0.0236059000
_diffrn_orient_matrix_UB_33      -0.0004723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         2.603
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0638
_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/[\s^2^(Fo^2^)+(0.0723P)^2^+0.0175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1712
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2811
_reflns_number_total             5086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2017-0084_suppl.cif
_cod_data_source_block           exp_4680
_cod_depositor_comments
;

2025-04-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C14 H11 N2 O2'
_cod_original_formula_weight         239.25
_cod_original_formula_moiety         'C9 H7 N O2, 0.5(C10 H8 N2)'
_cod_original_formula_units_Z            4
_cod_database_code               8105585
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C4(HD), C7(HE), C2(HF), C8(HH), C1(HI), N1(HB), C18(HG), C12(HJ), C13(HK),
 C15(HL), C16(HM), N4(HC), C20(H20), C19(H19), C22(H22), C23(H23), C28(H28),
 C25(H25), C27(H27), C26(H26)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(HA), O4(H)
;