#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:44:13 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247154.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_7247154
loop_
_publ_author_name
'Ejarque, Daniel'
'Calvet, Teresa'
'Font-Bardia, Mercè'
'Pons, Josefina'
_publ_section_title
;
 Virtual assessment achieved two binary cocrystals based on a liquid and a
 solid pyridine derivative with modulated thermal stabilities
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4798
_journal_page_last               4811
_journal_paper_doi               10.1039/D3CE00608E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H13 N O5'
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-06-06 deposited with the CCDC.	2023-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                94.585(2)
_cell_angle_beta                 101.837(2)
_cell_angle_gamma                115.880(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4176(5)
_cell_length_b                   7.5344(5)
_cell_length_c                   13.4049(9)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      3.06
_cell_volume                     647.36(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34534
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_min         3.062
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0392
_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)+(0.0668P)²+0.1850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3380
_reflns_number_total             3980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00608e2.cif
_cod_data_source_block           mo_C20VB158_0m_a
_cod_depositor_comments
'Adding full bibliography for 7247154--7247155.cif.'
_cod_database_code               7247154
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25197(11) 0.49759(11) 0.61464(5) 0.01586(16) Uani 1 1 d . . . . .
H1O H 0.323273 0.567738 0.577931 0.019 Uiso 1 1 calc R U . . .
N1 N 0.45711(13) 0.69762(13) 0.48906(7) 0.01443(17) Uani 1 1 d . . . . .
O2 O 0.50837(11) 0.73560(10) 0.74431(6) 0.01595(16) Uani 1 1 d . . . . .
O3 O -0.05997(11) 0.17973(11) 0.99786(5) 0.01565(16) Uani 1 1 d . . . . .
O4 O 0.23834(11) 0.48252(11) 1.06283(5) 0.01637(16) Uani 1 1 d . . . . .
O5 O 0.90935(11) 1.16970(11) 0.29797(6) 0.01873(17) Uani 1 1 d . . . . .
C1 C 0.34402(14) 0.58035(14) 0.71345(7) 0.01162(18) Uani 1 1 d . . . . .
C2 C 0.22959(14) 0.46674(13) 0.78569(7) 0.01076(17) Uani 1 1 d . . . . .
C3 C 0.04919(14) 0.28466(14) 0.74751(7) 0.01248(18) Uani 1 1 d . . . . .
H3 H -0.001122 0.234611 0.674714 0.015 Uiso 1 1 calc R U . . .
C4 C -0.06034(14) 0.17307(14) 0.81354(7) 0.01334(18) Uani 1 1 d . . . . .
H4 H -0.183068 0.048525 0.787565 0.016 Uiso 1 1 calc R U . . .
C5 C 0.01984(14) 0.25400(14) 0.91785(7) 0.01183(18) Uani 1 1 d . . . . .
C6 C 0.10344(16) 0.30008(16) 1.09048(8) 0.0182(2) Uani 1 1 d . . . . .
H6A H 0.044348 0.330343 1.145449 0.022 Uiso 1 1 calc R U . . .
H6B H 0.181433 0.227514 1.116641 0.022 Uiso 1 1 calc R U . . .
C7 C 0.19984(14) 0.43649(14) 0.95651(7) 0.01164(18) Uani 1 1 d . . . . .
C8 C 0.30875(14) 0.54705(14) 0.89307(7) 0.01188(18) Uani 1 1 d . . . . .
H8 H 0.431299 0.671415 0.920068 0.014 Uiso 1 1 calc R U . . .
C9 C 0.73962(15) 1.02225(14) 0.26744(7) 0.01287(18) Uani 1 1 d . . . . .
C10 C 0.63825(14) 0.90711(14) 0.34430(7) 0.01159(17) Uani 1 1 d . . . . .
C11 C 0.44777(15) 0.73375(14) 0.31284(7) 0.01352(18) Uani 1 1 d . . . . .
H11 H 0.376813 0.684203 0.241195 0.016 Uiso 1 1 calc R U . . .
C12 C 0.36274(15) 0.63413(14) 0.38742(8) 0.01457(19) Uani 1 1 d . . . . .
H12 H 0.232374 0.516211 0.365389 0.017 Uiso 1 1 calc R U . . .
C14 C 0.64183(16) 0.86330(15) 0.51950(8) 0.0169(2) Uani 1 1 d . . . . .
H14 H 0.710398 0.907507 0.591595 0.020 Uiso 1 1 calc R U . . .
C15 C 0.73707(15) 0.97284(15) 0.45038(8) 0.01540(19) Uani 1 1 d . . . . .
H15 H 0.867263 1.090552 0.474767 0.018 Uiso 1 1 calc R U . . .
C16 C 0.62636(16) 0.94678(15) 0.15402(8) 0.01568(19) Uani 1 1 d . . . . .
H16A H 0.705521 1.038780 0.113280 0.024 Uiso 1 1 calc R U . . .
H16B H 0.488415 0.939781 0.142547 0.024 Uiso 1 1 calc R U . . .
H16C H 0.611316 0.812589 0.132333 0.024 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C1 O1 H1O 109.5 . . ?
C12 N1 C14 118.36(8) . . ?
C5 O3 C6 104.62(7) . . ?
C7 O4 C6 104.80(7) . . ?
O2 C1 O1 123.78(8) . . ?
O2 C1 C2 122.43(8) . . ?
O1 C1 C2 113.79(8) . . ?
C3 C2 C8 120.91(8) . . ?
C3 C2 C1 120.49(8) . . ?
C8 C2 C1 118.60(8) . . ?
C2 C3 C4 121.83(9) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.25(8) . . ?
C5 C4 H4 121.9 . . ?
C3 C4 H4 121.9 . . ?
O3 C5 C4 127.95(8) . . ?
O3 C5 C7 109.83(8) . . ?
C4 C5 C7 122.19(8) . . ?
O4 C6 O3 106.97(7) . . ?
O4 C6 H6A 110.3 . . ?
O3 C6 H6A 110.3 . . ?
O4 C6 H6B 110.3 . . ?
O3 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
C8 C7 O4 128.51(8) . . ?
C8 C7 C5 122.26(9) . . ?
O4 C7 C5 109.19(8) . . ?
C7 C8 C2 116.56(8) . . ?
C7 C8 H8 121.7 . . ?
C2 C8 H8 121.7 . . ?
O5 C9 C16 122.18(9) . . ?
O5 C9 C10 119.87(9) . . ?
C16 C9 C10 117.94(8) . . ?
C11 C10 C15 118.21(8) . . ?
C11 C10 C9 121.94(8) . . ?
C15 C10 C9 119.85(8) . . ?
C12 C11 C10 119.18(9) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N1 C12 C11 122.57(9) . . ?
N1 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N1 C14 C15 122.86(9) . . ?
N1 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C14 C15 C10 118.80(9) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3170(11) . ?
O1 H1O 0.8400 . ?
N1 C12 1.3370(12) . ?
N1 C14 1.3410(13) . ?
O2 C1 1.2233(11) . ?
O3 C5 1.3716(11) . ?
O3 C6 1.4408(12) . ?
O4 C7 1.3786(11) . ?
O4 C6 1.4356(12) . ?
O5 C9 1.2172(12) . ?
C1 C2 1.4921(13) . ?
C2 C3 1.3924(13) . ?
C2 C8 1.4095(13) . ?
C3 C4 1.4029(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3736(13) . ?
C4 H4 0.9500 . ?
C5 C7 1.3933(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.3702(13) . ?
C8 H8 0.9500 . ?
C9 C16 1.5038(14) . ?
C9 C10 1.5069(13) . ?
C10 C11 1.3917(13) . ?
C10 C15 1.3955(13) . ?
C11 C12 1.3878(13) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.3859(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
