#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:23:23 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229083 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/10/7231090.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7231090
loop_
_publ_author_name
'Ion, Adrian E.'
'Dogaru, Andreea'
'Shova, Sergiu'
'Madalan, Augustin M.'
'Akintola, Oluseun'
'Ionescu, Sorana'
'Voicescu, Mariana'
'Nica, Simona'
'Buchholz, Axel'
'Plass, Winfried'
'Andruh, Marius'
_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_sum            'C31 H25.5 N2.5 O7'
_chemical_formula_weight         545.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2a 2n'
_space_group_name_H-M_alt        'P n c a'
_symmetry_space_group_name_Hall  '-P 2a 2n'
_symmetry_space_group_name_H-M   'P n c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1102(5)
_cell_length_b                   14.3955(6)
_cell_length_c                   30.2012(14)
_cell_measurement_reflns_used    23175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      1.95
_cell_volume                     5699.8(4)
_computing_cell_refinement       X-Area
_computing_data_collection       X-Area
_computing_data_reduction        X-Area
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE-IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            56098
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.057
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.0087(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0680
_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/[σ²(Fo²)+(0.1414P)²+0.8289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1947
_refine_ls_wR_factor_ref         0.2262
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3618
_reflns_number_total             5587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00945g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7231086--7231091.cif.
;
_cod_original_formula_sum        'C31 H25.50 N2.50 O7'
_cod_database_code               7231090
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 1.0915(2) 0.2045(2) 0.13253(10) 0.0632(8) Uani 1 1 d . . .
H1 H 1.0643 0.2298 0.1068 0.076 Uiso 1 1 calc R U .
C2 C 1.1927(2) 0.1823(2) 0.13395(10) 0.0600(7) Uani 1 1 d . . .
H2 H 1.2340 0.1945 0.1096 0.072 Uiso 1 1 calc R U .
C3 C 1.23438(19) 0.14157(19) 0.17171(9) 0.0533(6) Uani 1 1 d . . .
C4 C 1.1690(2) 0.1287(2) 0.20777(10) 0.0572(7) Uani 1 1 d . . .
H4 H 1.1938 0.1026 0.2338 0.069 Uiso 1 1 calc R U .
C5 C 1.0691(2) 0.1540(2) 0.20501(10) 0.0603(7) Uani 1 1 d . . .
H5 H 1.0266 0.1461 0.2294 0.072 Uiso 1 1 calc R U .
C6 C 1.34155(19) 0.11433(19) 0.17442(10) 0.0545(6) Uani 1 1 d . . .
C7 C 1.40023(19) 0.12014(19) 0.21316(10) 0.0558(7) Uani 1 1 d . . .
H7 H 1.3758 0.1396 0.2405 0.067 Uiso 1 1 calc R U .
C8 C 1.50005(18) 0.09273(19) 0.20481(10) 0.0542(7) Uani 1 1 d . . .
C9 C 1.58263(18) 0.09750(19) 0.23771(11) 0.0560(7) Uani 1 1 d . . .
C10 C 1.5644(2) 0.0766(2) 0.28171(11) 0.0637(8) Uani 1 1 d . . .
H10 H 1.5004 0.0559 0.2906 0.076 Uiso 1 1 calc R U .
C11 C 1.6407(2) 0.0864(2) 0.31213(12) 0.0702(8) Uani 1 1 d . . .
H11 H 1.6262 0.0735 0.3416 0.084 Uiso 1 1 calc R U .
C12 C 1.7532(2) 0.1328(2) 0.25961(12) 0.0655(8) Uani 1 1 d . . .
H12 H 1.8185 0.1521 0.2519 0.079 Uiso 1 1 calc R U .
C13 C 1.6813(2) 0.1258(2) 0.22680(11) 0.0604(7) Uani 1 1 d . . .
H13 H 1.6980 0.1398 0.1976 0.072 Uiso 1 1 calc R U .
C14 C 1.50604(19) 0.06331(19) 0.16039(10) 0.0567(7) Uani 1 1 d . . .
C15 C 1.5900(2) 0.0217(2) 0.14034(12) 0.0681(8) Uani 1 1 d . . .
H15 H 1.6475 0.0160 0.1582 0.082 Uiso 1 1 calc R U .
C16 C 1.6004(3) -0.0124(3) 0.09784(15) 0.0825(10) Uani 1 1 d . . .
H16 H 1.6646 -0.0357 0.0908 0.099 Uiso 1 1 calc R U .
C17 C 1.5296(3) -0.0165(3) 0.06478(14) 0.0879(11) Uani 1 1 d . . .
H17 H 1.5524 -0.0427 0.0384 0.106 Uiso 1 1 calc R U .
C18 C 1.4282(3) 0.0127(3) 0.06472(12) 0.0837(11) Uani 1 1 d . . .
H18 H 1.3925 0.0033 0.0385 0.100 Uiso 1 1 calc R U .
C19 C 1.3745(2) 0.0537(2) 0.09854(11) 0.0686(8) Uani 1 1 d . . .
H19 H 1.3069 0.0672 0.0918 0.082 Uiso 1 1 calc R U .
C20 C 1.40403(19) 0.07802(19) 0.14049(10) 0.0550(7) Uani 1 1 d . . .
C21 C 0.81928(19) 0.2400(2) 0.11634(9) 0.0552(7) Uani 1 1 d . . .
C22 C 0.70934(18) 0.25423(18) 0.10357(9) 0.0489(6) Uani 1 1 d . . .
C23 C 0.6778(2) 0.23863(19) 0.06050(9) 0.0535(6) Uani 1 1 d . . .
H23 H 0.7251 0.2197 0.0394 0.064 Uiso 1 1 calc R U .
C24 C 0.5764(2) 0.2509(2) 0.04836(9) 0.0547(7) Uani 1 1 d . . .
C25 C 0.5449(2) 0.2339(3) 0.00204(10) 0.0674(8) Uani 1 1 d . . .
C26 C 0.50665(19) 0.28086(19) 0.07982(9) 0.0540(7) Uani 1 1 d . . .
H26 H 0.4387 0.2893 0.0719 0.065 Uiso 1 1 calc R U .
C27 C 0.53751(18) 0.29832(18) 0.12295(9) 0.0481(6) Uani 1 1 d . . .
C28 C 0.46347(19) 0.3321(2) 0.15653(10) 0.0537(6) Uani 1 1 d . . .
C29 C 0.63866(18) 0.28421(18) 0.13475(9) 0.0477(6) Uani 1 1 d . . .
H29 H 0.6593 0.2949 0.1638 0.057 Uiso 1 1 calc R U .
C31 C 0.7500 0.5000 0.1662(4) 0.313(14) Uani 1 2 d S T P
C32 C 0.8291(9) 0.4844(6) 0.0998(5) 0.350(10) Uani 1 1 d . . .
H32A H 0.8064 0.4889 0.0697 0.525 Uiso 1 1 calc R U .
H32B H 0.8813 0.5299 0.1051 0.525 Uiso 1 1 calc R U .
H32C H 0.8560 0.4234 0.1051 0.525 Uiso 1 1 calc R U .
C33 C 0.2410(15) 0.4114(10) 0.0434(6) 0.214(10) Uani 0.5 1 d . . P
N1 N 1.03095(17) 0.19049(18) 0.16738(8) 0.0596(6) Uani 1 1 d . . .
N2 N 1.73470(18) 0.11366(19) 0.30169(10) 0.0671(7) Uani 1 1 d . . .
N3 N 0.7500 0.5000 0.1272(2) 0.123(2) Uani 1 2 d S T P
O1 O 0.83842(14) 0.23109(18) 0.15690(7) 0.0745(7) Uani 1 1 d . . .
O2 O 0.88488(15) 0.23781(19) 0.08687(7) 0.0776(7) Uani 1 1 d . . .
O3 O 0.60247(19) 0.2089(2) -0.02661(9) 0.0982(9) Uani 1 1 d . . .
O4 O 0.44725(17) 0.2473(2) -0.00507(8) 0.0912(9) Uani 1 1 d . . .
H4A H 0.4341 0.2361 -0.0311 0.137 Uiso 1 1 calc R U .
O5 O 0.37288(14) 0.34877(19) 0.14031(7) 0.0754(7) Uani 1 1 d . . .
H5A H 0.3353 0.3675 0.1601 0.113 Uiso 1 1 calc R U .
O6 O 0.48605(16) 0.34397(18) 0.19484(7) 0.0753(7) Uani 1 1 d . . .
O7 O 0.7896(6) 0.4833(7) 0.1996(3) 0.137(3) Uani 0.5 1 d . . P
O9 O 0.2500 0.5000 0.0388(3) 0.478(16) Uani 1 2 d S T P
H1N H 0.950(3) 0.204(3) 0.1629(13) 0.094(11) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 121.2(3) . .
C1 C2 C3 120.3(3) . .
C2 C3 C4 116.9(2) . .
C2 C3 C6 122.4(3) . .
C4 C3 C6 120.7(3) . .
C5 C4 C3 120.4(3) . .
N1 C5 C4 120.8(3) . .
C7 C6 C20 108.0(2) . .
C7 C6 C3 123.9(3) . .
C20 C6 C3 128.1(3) . .
C8 C7 C6 110.4(3) . .
C7 C8 C14 108.1(2) . .
C7 C8 C9 123.9(3) . .
C14 C8 C9 128.0(2) . .
C10 C9 C13 116.7(3) . .
C10 C9 C8 120.8(3) . .
C13 C9 C8 122.4(3) . .
C11 C10 C9 119.9(3) . .
N2 C11 C10 123.3(3) . .
N2 C12 C13 123.6(3) . .
C12 C13 C9 119.2(3) . .
C15 C14 C8 126.0(3) . .
C15 C14 C20 126.8(3) . .
C8 C14 C20 107.0(2) . .
C16 C15 C14 129.5(3) . .
C17 C16 C15 128.9(3) . .
C16 C17 C18 129.5(3) . .
C19 C18 C17 128.1(3) . .
C20 C19 C18 130.7(3) . .
C19 C20 C6 127.0(3) . .
C19 C20 C14 126.4(3) . .
C6 C20 C14 106.4(2) . .
O2 C21 O1 124.0(2) . .
O2 C21 C22 118.9(2) . .
O1 C21 C22 117.0(2) . .
C23 C22 C29 119.2(2) . .
C23 C22 C21 120.3(2) . .
C29 C22 C21 120.4(2) . .
C22 C23 C24 120.9(2) . .
C26 C24 C23 119.3(3) . .
C26 C24 C25 121.0(2) . .
C23 C24 C25 119.7(3) . .
O3 C25 O4 122.6(3) . .
O3 C25 C24 123.7(3) . .
O4 C25 C24 113.7(3) . .
C27 C26 C24 120.5(2) . .
C26 C27 C29 119.6(2) . .
C26 C27 C28 120.7(2) . .
C29 C27 C28 119.8(2) . .
O6 C28 O5 123.8(3) . .
O6 C28 C27 122.7(2) . .
O5 C28 C27 113.5(2) . .
C27 C29 C22 120.5(2) . .
O7 C31 O7 59.2(9) . 2_665
O7 C31 N3 150.4(5) . .
O7 C31 N3 150.4(5) 2_665 .
C1 N1 C5 120.2(2) . .
C12 N2 C11 117.3(3) . .
C31 N3 C32 128.0(7) . 2_665
C31 N3 C32 128.0(7) . .
C32 N3 C32 104.1(15) 2_665 .
O7 O7 C31 60.4(5) 2_665 .
C33 O9 C33 167.6(18) 2_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.334(4) .
C1 C2 1.365(4) .
C2 C3 1.394(4) .
C3 C4 1.399(4) .
C3 C6 1.461(3) .
C4 C5 1.362(4) .
C5 N1 1.348(4) .
C6 C7 1.403(4) .
C6 C20 1.412(4) .
C7 C8 1.390(4) .
C8 C14 1.409(4) .
C8 C9 1.471(4) .
C9 C10 1.383(5) .
C9 C13 1.395(4) .
C10 C11 1.365(4) .
C11 N2 1.331(4) .
C12 N2 1.323(4) .
C12 C13 1.371(4) .
C14 C15 1.392(4) .
C14 C20 1.481(4) .
C15 C16 1.381(5) .
C16 C17 1.365(6) .
C17 C18 1.395(5) .
C18 C19 1.374(5) .
C19 C20 1.370(4) .
C21 O2 1.238(3) .
C21 O1 1.257(3) .
C21 C22 1.506(3) .
C22 C23 1.383(4) .
C22 C29 1.390(4) .
C23 C24 1.390(4) .
C24 C26 1.388(4) .
C24 C25 1.479(4) .
C25 O3 1.203(4) .
C25 O4 1.313(4) .
C26 C27 1.387(4) .
C27 C29 1.388(3) .
C27 C28 1.486(4) .
C28 O6 1.206(3) .
C28 O5 1.307(3) .
C31 O7 1.159(11) .
C31 O7 1.159(11) 2_665
C31 N3 1.177(13) .
C32 N3 1.345(8) .
C33 O9 1.289(14) .
N3 C32 1.345(8) 2_665
O7 O7 1.145(15) 2_665
O9 C33 1.289(14) 2_565
