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_7231088
_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         'C9 H6 O6, C20 H14 N2, 0.85(H2 O)'
_chemical_formula_sum            'C29 H21.7 N2 O6.85'
_chemical_formula_weight         507.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-14
_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                 117.943(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.627(2)
_cell_length_b                   7.3399(7)
_cell_length_c                   20.281(3)
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7550
_cell_measurement_theta_min      2.1220
_cell_volume                     2844.1(6)
_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      293(2)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
  1 omega   53.00   95.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  178.0000 -150.0000 42

  2 omega    3.00   89.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127   19.0000 -180.0000 86

  3 omega   40.00   69.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  178.0000  -60.0000 29

  4 omega  -81.00  -47.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000 -180.0000 34

  5 omega  -47.00   -3.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -57.0000 -120.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0266485000
_diffrn_orient_matrix_UB_12      -0.0629262000
_diffrn_orient_matrix_UB_13      0.0219094000
_diffrn_orient_matrix_UB_21      0.0097077000
_diffrn_orient_matrix_UB_22      0.0560169000
_diffrn_orient_matrix_UB_23      0.0318633000
_diffrn_orient_matrix_UB_31      -0.0239532000
_diffrn_orient_matrix_UB_32      -0.0473676000
_diffrn_orient_matrix_UB_33      0.0085094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4957
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.01
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74210
_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 light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1058
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4957
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1072P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2523
_reflns_number_gt                2450
_reflns_number_total             4957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00945g2.cif
_cod_data_source_block           shi_2460_sini
_cod_depositor_comments
'Adding full bibliography for 7231086--7231091.cif.'
_cod_original_cell_volume        2844.1(5)
_cod_original_formula_sum        'C29 H21.70 N2 O6.85'
_cod_database_code               7231088
_chemical_oxdiff_formula         'C25 H30 N2 O6'
_chemical_oxdiff_usercomment     S_32
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.570(3)
 0.430(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
C14 \\sim N1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: O1W(0.15) H1WA(0.15) H1WB(0.15) O4W(0.05) H4WA(0.05) H4WB(0.05)
 O8W(0.1) H8WA(0.1) H8WB(0.1) O2W(0.15) H2WA(0.15) H2WB(0.15) O6W(0.15)
 H6WA(0.15) H6WB(0.15) O5W(0.05) H5WA(0.05) H5WB(0.05) O7W(0.1) H7WA(0.1)
 H7WB(0.1) O3W(0.1) H3WA(0.1) H3WB(0.1)
5.a Riding coordinates:
 O1(H1), O5(H5), O1W(H1WA,H1WB), O4W(H4WA,H4WB), O8W(H8WA,H8WB), O2W(H2WA,
 H2WB), O6W(H6WA,H6WB), O5W(H5WA,H5WB), O7W(H7WA,H7WB), O3W(H3WA,H3WB)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C29(H29), C30(H30), C28(H28), C27(H27), C24(H24), C23(H23), C22(H22), C21(H21),
  C20(H20)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'