#------------------------------------------------------------------------------
#$Date: 2022-02-25 01:38:21 +0200 (Fri, 25 Feb 2022) $
#$Revision: 273148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244518.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_7244518
loop_
_publ_author_name
'Fedyanin, Ivan V.'
_publ_section_title
;
 Control of supramolecular chirality in co-crystals of achiral molecules
 via stacking interactions and hydrogen bonding
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00081D
_journal_year                    2022
_chemical_formula_moiety         'C18 H12, C5 H3 N3 O5'
_chemical_formula_sum            'C23 H15 N3 O5'
_chemical_formula_weight         413.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           'Modified SHELXL output'
_audit_update_record
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6442(3)
_cell_length_b                   8.6092(3)
_cell_length_c                   27.0462(9)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      2.77
_cell_volume                     1779.92(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'ο scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            44112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_min         2.483
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         7853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0416
_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)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6771
_reflns_number_total             7853
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00081d2.cif
_cod_data_source_block           35dnp2o-tph
_cod_database_code               7244518
_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru
_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.
;
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O2 O 0.55823(18) 0.63401(13) 0.25283(4) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.67961(17) 0.38712(12) 0.20099(4) 0.0204(2) Uani 1 1 d . . . . .
O4 O 0.87388(18) 0.44544(15) 0.14623(5) 0.0275(3) Uani 1 1 d . . . . .
O5 O 0.80795(17) 0.92247(14) 0.05590(4) 0.0230(2) Uani 1 1 d . . . . .
O6 O 0.67345(19) 1.11524(13) 0.09070(5) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.55651(18) 0.85813(14) 0.20946(5) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.505(3) 0.904(3) 0.2348(9) 0.027(6) Uiso 1 1 d . . . . .
N3 N 0.75260(18) 0.47982(14) 0.17354(5) 0.0162(2) Uani 1 1 d . . . . .
N5 N 0.72352(18) 0.98006(15) 0.08962(5) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.5987(2) 0.70116(16) 0.21488(6) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.69362(19) 0.64065(15) 0.17279(5) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.73493(19) 0.72766(15) 0.13240(5) 0.0137(2) Uani 1 1 d . . . . .
H4 H 0.798589 0.684051 0.105618 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6813(2) 0.88257(15) 0.13138(5) 0.0134(2) Uani 1 1 d . . . . .
C6 C 0.5936(2) 0.94587(16) 0.17013(5) 0.0150(2) Uani 1 1 d . . . . .
H6 H 0.558932 1.051800 0.169256 0.018 Uiso 1 1 calc R U . . .
C1T C 0.2769(2) 0.54502(17) 0.14715(6) 0.0197(3) Uani 1 1 d . . . . .
H1T H 0.220382 0.532506 0.178172 0.024 Uiso 1 1 calc R U . . .
C2T C 0.3657(2) 0.42152(17) 0.12686(7) 0.0226(3) Uani 1 1 d . . . . .
H2T H 0.368696 0.324619 0.143635 0.027 Uiso 1 1 calc R U . . .
C3T C 0.4507(2) 0.43847(17) 0.08196(7) 0.0225(3) Uani 1 1 d . . . . .
H3T H 0.514112 0.353890 0.068275 0.027 Uiso 1 1 calc R U . . .
C4T C 0.4431(2) 0.57778(17) 0.05720(6) 0.0192(3) Uani 1 1 d . . . . .
H4T H 0.501014 0.588010 0.026287 0.023 Uiso 1 1 calc R U . . .
C5T C 0.3513(2) 0.70564(16) 0.07674(6) 0.0153(3) Uani 1 1 d . . . . .
C6T C 0.3424(2) 0.85317(16) 0.05004(6) 0.0158(3) Uani 1 1 d . . . . .
C7T C 0.4313(2) 0.87491(19) 0.00512(6) 0.0206(3) Uani 1 1 d . . . . .
H7T H 0.499262 0.792383 -0.008088 0.025 Uiso 1 1 calc R U . . .
C8T C 0.4218(3) 1.0135(2) -0.02017(7) 0.0255(3) Uani 1 1 d . . . . .
H8T H 0.484757 1.026684 -0.050152 0.031 Uiso 1 1 calc R U . . .
C9T C 0.3200(3) 1.13383(19) -0.00175(7) 0.0258(3) Uani 1 1 d . . . . .
H9T H 0.310792 1.228667 -0.019516 0.031 Uiso 1 1 calc R U . . .
C10T C 0.2327(2) 1.11550(18) 0.04212(6) 0.0220(3) Uani 1 1 d . . . . .
H10T H 0.162619 1.198301 0.054220 0.026 Uiso 1 1 calc R U . . .
C11T C 0.2442(2) 0.97725(16) 0.06977(6) 0.0160(3) Uani 1 1 d . . . . .
C12T C 0.1638(2) 0.96266(16) 0.11837(6) 0.0158(2) Uani 1 1 d . . . . .
C13T C 0.0748(2) 1.08795(18) 0.14070(7) 0.0208(3) Uani 1 1 d . . . . .
H13T H 0.063156 1.182811 0.123063 0.025 Uiso 1 1 calc R U . . .
C14T C 0.0048(2) 1.0762(2) 0.18723(7) 0.0246(3) Uani 1 1 d . . . . .
H14T H -0.056123 1.161721 0.201226 0.030 Uiso 1 1 calc R U . . .
C15T C 0.0229(2) 0.9389(2) 0.21395(7) 0.0245(3) Uani 1 1 d . . . . .
H15T H -0.022820 0.931231 0.246517 0.029 Uiso 1 1 calc R U . . .
C16T C 0.1074(2) 0.8147(2) 0.19282(6) 0.0210(3) Uani 1 1 d . . . . .
H16T H 0.118304 0.721054 0.211134 0.025 Uiso 1 1 calc R U . . .
C17T C 0.1781(2) 0.82203(16) 0.14502(6) 0.0158(2) Uani 1 1 d . . . . .
C18T C 0.26811(19) 0.68971(16) 0.12291(6) 0.0152(2) Uani 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
_geom_angle_publ_flag
C6 N1 C2 125.59(13) . . ?
C6 N1 H1 117.5(15) . . ?
C2 N1 H1 116.9(15) . . ?
O4 N3 O3 123.67(13) . . ?
O4 N3 C3 117.19(13) . . ?
O3 N3 C3 119.14(13) . . ?
O5 N5 O6 124.60(13) . . ?
O5 N5 C5 117.77(12) . . ?
O6 N5 C5 117.64(13) . . ?
O2 C2 N1 119.28(14) . . ?
O2 C2 C3 128.27(13) . . ?
N1 C2 C3 112.42(12) . . ?
C4 C3 C2 123.32(12) . . ?
C4 C3 N3 117.54(12) . . ?
C2 C3 N3 119.12(12) . . ?
C3 C4 C5 118.26(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.87(13) . . ?
C6 C5 N5 118.73(12) . . ?
C4 C5 N5 120.37(13) . . ?
N1 C6 C5 119.51(13) . . ?
N1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C2T C1T C18T 121.42(16) . . ?
C2T C1T H1T 119.3 . . ?
C18T C1T H1T 119.3 . . ?
C1T C2T C3T 119.99(15) . . ?
C1T C2T H2T 120.0 . . ?
C3T C2T H2T 120.0 . . ?
C4T C3T C2T 119.96(15) . . ?
C4T C3T H3T 120.0 . . ?
C2T C3T H3T 120.0 . . ?
C3T C4T C5T 121.32(16) . . ?
C3T C4T H4T 119.3 . . ?
C5T C4T H4T 119.3 . . ?
C18T C5T C4T 118.80(13) . . ?
C18T C5T C6T 120.11(13) . . ?
C4T C5T C6T 121.09(14) . . ?
C7T C6T C11T 118.94(13) . . ?
C7T C6T C5T 121.37(14) . . ?
C11T C6T C5T 119.69(14) . . ?
C8T C7T C6T 121.31(16) . . ?
C8T C7T H7T 119.3 . . ?
C6T C7T H7T 119.3 . . ?
C7T C8T C9T 119.87(17) . . ?
C7T C8T H8T 120.1 . . ?
C9T C8T H8T 120.1 . . ?
C10T C9T C8T 119.84(15) . . ?
C10T C9T H9T 120.1 . . ?
C8T C9T H9T 120.1 . . ?
C9T C10T C11T 121.80(16) . . ?
C9T C10T H10T 119.1 . . ?
C11T C10T H10T 119.1 . . ?
C10T C11T C6T 118.18(15) . . ?
C10T C11T C12T 121.72(14) . . ?
C6T C11T C12T 120.05(13) . . ?
C13T C12T C17T 118.28(14) . . ?
C13T C12T C11T 121.59(13) . . ?
C17T C12T C11T 120.11(13) . . ?
C14T C13T C12T 121.64(15) . . ?
C14T C13T H13T 119.2 . . ?
C12T C13T H13T 119.2 . . ?
C13T C14T C15T 120.02(16) . . ?
C13T C14T H14T 120.0 . . ?
C15T C14T H14T 120.0 . . ?
C16T C15T C14T 119.44(16) . . ?
C16T C15T H15T 120.3 . . ?
C14T C15T H15T 120.3 . . ?
C15T C16T C17T 121.97(16) . . ?
C15T C16T H16T 119.0 . . ?
C17T C16T H16T 119.0 . . ?
C16T C17T C12T 118.62(14) . . ?
C16T C17T C18T 121.62(14) . . ?
C12T C17T C18T 119.75(14) . . ?
C5T C18T C1T 118.49(13) . . ?
C5T C18T C17T 120.03(13) . . ?
C1T C18T C17T 121.47(14) . . ?
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
O2 C2 1.2179(18) . ?
O3 N3 1.2245(16) . ?
O4 N3 1.2217(18) . ?
O5 N5 1.2223(17) . ?
O6 N5 1.2254(17) . ?
N1 C6 1.3351(19) . ?
N1 C2 1.3970(18) . ?
N1 H1 0.89(2) . ?
N3 C3 1.4563(18) . ?
N5 C5 1.4435(18) . ?
C2 C3 1.447(2) . ?
C3 C4 1.362(2) . ?
C4 C5 1.3955(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.358(2) . ?
C6 H6 0.9500 . ?
C1T C2T 1.375(2) . ?
C1T C18T 1.409(2) . ?
C1T H1T 0.9500 . ?
C2T C3T 1.385(3) . ?
C2T H2T 0.9500 . ?
C3T C4T 1.375(2) . ?
C3T H3T 0.9500 . ?
C4T C5T 1.409(2) . ?
C4T H4T 0.9500 . ?
C5T C18T 1.408(2) . ?
C5T C6T 1.463(2) . ?
C6T C7T 1.404(2) . ?
C6T C11T 1.411(2) . ?
C7T C8T 1.377(2) . ?
C7T H7T 0.9500 . ?
C8T C9T 1.388(3) . ?
C8T H8T 0.9500 . ?
C9T C10T 1.370(3) . ?
C9T H9T 0.9500 . ?
C10T C11T 1.408(2) . ?
C10T H10T 0.9500 . ?
C11T C12T 1.456(2) . ?
C12T C13T 1.411(2) . ?
C12T C17T 1.413(2) . ?
C13T C14T 1.371(3) . ?
C13T H13T 0.9500 . ?
C14T C15T 1.392(3) . ?
C14T H14T 0.9500 . ?
C15T C16T 1.374(2) . ?
C15T H15T 0.9500 . ?
C16T C17T 1.402(2) . ?
C16T H16T 0.9500 . ?
C17T C18T 1.459(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.89(2) 2.07(2) 2.7297(17) 131(2) 3_655 yes
N1 H1 O3 0.89(2) 2.24(2) 3.0310(18) 149(2) 3_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O2 179.61(16) . . . . ?
C6 N1 C2 C3 1.4(2) . . . . ?
O2 C2 C3 C4 -178.66(16) . . . . ?
N1 C2 C3 C4 -0.6(2) . . . . ?
O2 C2 C3 N3 -0.2(2) . . . . ?
N1 C2 C3 N3 177.86(13) . . . . ?
O4 N3 C3 C4 20.5(2) . . . . ?
O3 N3 C3 C4 -159.51(14) . . . . ?
O4 N3 C3 C2 -158.10(15) . . . . ?
O3 N3 C3 C2 21.9(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
N3 C3 C4 C5 -179.20(13) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C5 N5 179.33(13) . . . . ?
O5 N5 C5 C6 177.42(14) . . . . ?
O6 N5 C5 C6 -1.9(2) . . . . ?
O5 N5 C5 C4 -0.5(2) . . . . ?
O6 N5 C5 C4 -179.88(14) . . . . ?
C2 N1 C6 C5 -0.7(2) . . . . ?
C4 C5 C6 N1 -0.8(2) . . . . ?
N5 C5 C6 N1 -178.71(13) . . . . ?
C18T C1T C2T C3T 0.8(3) . . . . ?
C1T C2T C3T C4T -1.4(3) . . . . ?
C2T C3T C4T C5T 0.5(3) . . . . ?
C3T C4T C5T C18T 0.9(2) . . . . ?
C3T C4T C5T C6T -179.48(15) . . . . ?
C18T C5T C6T C7T 176.80(14) . . . . ?
C4T C5T C6T C7T -2.8(2) . . . . ?
C18T C5T C6T C11T -2.6(2) . . . . ?
C4T C5T C6T C11T 177.74(14) . . . . ?
C11T C6T C7T C8T -1.1(2) . . . . ?
C5T C6T C7T C8T 179.50(15) . . . . ?
C6T C7T C8T C9T -1.3(3) . . . . ?
C7T C8T C9T C10T 1.6(3) . . . . ?
C8T C9T C10T C11T 0.6(3) . . . . ?
C9T C10T C11T C6T -2.9(2) . . . . ?
C9T C10T C11T C12T 174.62(16) . . . . ?
C7T C6T C11T C10T 3.1(2) . . . . ?
C5T C6T C11T C10T -177.47(14) . . . . ?
C7T C6T C11T C12T -174.48(14) . . . . ?
C5T C6T C11T C12T 5.0(2) . . . . ?
C10T C11T C12T C13T -1.9(2) . . . . ?
C6T C11T C12T C13T 175.61(14) . . . . ?
C10T C11T C12T C17T 179.98(15) . . . . ?
C6T C11T C12T C17T -2.6(2) . . . . ?
C17T C12T C13T C14T 0.7(2) . . . . ?
C11T C12T C13T C14T -177.51(15) . . . . ?
C12T C13T C14T C15T 1.0(3) . . . . ?
C13T C14T C15T C16T -1.6(3) . . . . ?
C14T C15T C16T C17T 0.6(3) . . . . ?
C15T C16T C17T C12T 1.1(2) . . . . ?
C15T C16T C17T C18T 179.80(15) . . . . ?
C13T C12T C17T C16T -1.7(2) . . . . ?
C11T C12T C17T C16T 176.55(14) . . . . ?
C13T C12T C17T C18T 179.56(14) . . . . ?
C11T C12T C17T C18T -2.2(2) . . . . ?
C4T C5T C18T C1T -1.4(2) . . . . ?
C6T C5T C18T C1T 178.94(14) . . . . ?
C4T C5T C18T C17T 177.50(14) . . . . ?
C6T C5T C18T C17T -2.1(2) . . . . ?
C2T C1T C18T C5T 0.6(2) . . . . ?
C2T C1T C18T C17T -178.31(15) . . . . ?
C16T C17T C18T C5T -174.19(14) . . . . ?
C12T C17T C18T C5T 4.5(2) . . . . ?
C16T C17T C18T C1T 4.7(2) . . . . ?
C12T C17T C18T C1T -176.54(14) . . . . ?
