Organic co-crystals of 1,3-bis(4-pyridyl)azulene with a series of hydrogen-bond donors
Ion, Adrian E.; Dogaru, Andreea; Shova, Sergiu; Madalan, Augustin M.; Akintola, Oluseun; Ionescu, Sorana; Voicescu, Mariana; Nica, Simona; Buchholz, Axel; Plass, Winfried; Andruh, Marius; CrystEngComm 20 (2018) 4463–; doi:10.1039/C8CE00945G

data_7231087
_publ_section_title
;
 Organic co-crystals of 1,3-bis(4-pyridyl)azulene with a series of
 hydrogen-bond donors
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              4463
_journal_paper_doi               10.1039/C8CE00945G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C20 H15 N2, C20 H14 N2, C8 H6 O4'
_chemical_formula_sum            'C48 H35 N4 O4'
_chemical_formula_weight         731.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4512(9)
_cell_length_b                   19.7388(14)
_cell_length_c                   14.6081(15)
_cell_measurement_reflns_used    1556
_cell_measurement_temperature    172.8(3)
_cell_measurement_theta_max      24.8360
_cell_measurement_theta_min      2.1310
_cell_volume                     3590.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      172.8(3)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   -4.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000  150.0000 28

  2 omega  -41.00   52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690   77.0000  -60.0000 93

  3 omega   37.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -180.0000 42
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0047042000
_diffrn_orient_matrix_UB_12      -0.0352357000
_diffrn_orient_matrix_UB_13      -0.0084698000
_diffrn_orient_matrix_UB_21      -0.0563517000
_diffrn_orient_matrix_UB_22      -0.0021291000
_diffrn_orient_matrix_UB_23      -0.0066466000
_diffrn_orient_matrix_UB_31      0.0071102000
_diffrn_orient_matrix_UB_32      0.0066195000
_diffrn_orient_matrix_UB_33      -0.0473498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9600
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0559
_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/[\s^2^(Fo^2^)+(0.0615P)^2^+0.8033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2306
_reflns_number_total             3269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00945g2.cif
_cod_data_source_block           shi_2617_sini
_cod_depositor_comments
'Adding full bibliography for 7231086--7231091.cif.'
_cod_original_cell_volume        3590.2(5)
_cod_database_code               7231087
_chemical_oxdiff_formula         'C25 H25 N2 O4'
_chemical_oxdiff_usercomment     S_44
_reflns_odcompleteness_completeness 99.93
_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 C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27), C3(H3),
 C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'