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_7231091
_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
'2(C20 H14 N2), 2(C14 H10 O5), 2(C2 H3 N), 0.75(H2 O)'
_chemical_formula_sum            'C72 H55.5 N6 O10.75'
_chemical_formula_weight         1176.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-16
_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                 104.831(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   52.2362(18)
_cell_length_b                   7.4175(3)
_cell_length_c                   32.1601(12)
_cell_measurement_reflns_used    8136
_cell_measurement_temperature    200.05(10)
_cell_measurement_theta_max      28.8196
_cell_measurement_theta_min      2.3349
_cell_volume                     12045.7(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.05(10)
_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  -15.00   16.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -99.0000  -60.0000 42

  2 omega  -82.00  -35.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563 -178.0000  -90.0000 62

  3 omega  -84.00   -4.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -57.0000  150.0000 106

  4 omega   25.00   95.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4563   19.0000  -60.0000 94

  5 omega  -90.00    3.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -57.0000   60.0000 124

  6 omega  -99.00  -36.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563 -178.0000    0.0000 84

  7 omega -102.00  -51.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  178.0000 -150.0000 67

  8 omega  -48.00   45.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4563  -57.0000 -180.0000 124
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0132568000
_diffrn_orient_matrix_UB_12      0.0183832000
_diffrn_orient_matrix_UB_13      0.0004277000
_diffrn_orient_matrix_UB_21      0.0037509000
_diffrn_orient_matrix_UB_22      0.0883335000
_diffrn_orient_matrix_UB_23      0.0075949000
_diffrn_orient_matrix_UB_31      -0.0027561000
_diffrn_orient_matrix_UB_32      0.0315967000
_diffrn_orient_matrix_UB_33      -0.0215100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            48203
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4924
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     926
_refine_ls_number_reflns         10638
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0862P)^2^+14.8588P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                7633
_reflns_number_total             10638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00945g2.cif
_cod_data_source_block           shi_1586_nica
_cod_depositor_comments
'Adding full bibliography for 7231086--7231091.cif.'
_cod_original_cell_volume        12045.6(7)
_cod_original_formula_sum        'C72 H55.50 N6 O10.75'
_cod_database_code               7231091
_chemical_oxdiff_formula         'C20 H20 O4 N2'
_chemical_oxdiff_usercomment     'S_17, rosu-brun?, 0.4x0.2x0.1'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 N3-C5 \\sim N2-C3 \\sim N1-C1
 with sigma of 0.001
 C3-C4 \\sim C2-C1 \\sim C6-C5
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uiso(N3) = Uiso(N2)
Uiso(C4) = Uiso(C6) = Uiso(C5) = Uiso(C3)
4. Others
 Fixed Sof: N2(0.75) C3(0.75) C4(0.75) H4C(0.75) H4D(0.75) H4E(0.75) N3(0.25)
 C5(0.25) C6(0.25) H6C(0.25) H6D(0.25) H6E(0.25) O2W(0.5) H2WA(0.5) H2WB(0.5)
 O1W(0.25) H1WA(0.25) H1WB(0.25)
5.a Riding coordinates:
 O1B(H1B), O4B(H4B), O4A(H4A), O1A(H1A), C4(H4C,H4D,H4E), C2(H2A,H2B,H2C),
 C6(H6C,H6D,H6E), O2W(H2WA,H2WB), O1W(H1WA,H1WB)
;
_olex2_submission_special_instructions 'No special instructions were received'