#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:05:17 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261634 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241759.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_7241759
loop_
_publ_author_name
'Tómasson, Daníel Arnar'
'Ghosh, Dipankar'
'Kurup, M. R. Prathapachandra'
'Mulvee, Matthew T.'
'Damodaran, Krishna K.'
_publ_section_title
;
 Evaluating the role of a urea-like motif in enhancing the thermal and
 mechanical strength of supramolecular gels
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              617
_journal_page_last               628
_journal_paper_doi               10.1039/D0CE01194K
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C18 H15 N5 O'
_chemical_formula_sum            'C18 H15 N5 O'
_chemical_formula_weight         317.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-29 deposited with the CCDC.	2020-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.8120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.84640(10)
_cell_length_b                   11.0679(3)
_cell_length_c                   35.2718(9)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.36
_cell_measurement_theta_min      2.51
_cell_volume                     1500.83(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.97
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            30671
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.080
_diffrn_reflns_theta_min         2.507
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1232 before and 0.0727 after correction. The Ratio of minimum to maximum transmission is 0.8186. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0460
_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)+(0.0574P)²+0.5908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2729
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01194k2.cif
_cod_data_source_block           Ligand_HL2
_cod_depositor_comments
'Adding full bibliography for 7241758--7241763.cif.'
_cod_database_code               7241759
_shelx_shelxl_version_number     2017/1
_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_max   0.978
_shelx_estimated_absorpt_t_min   0.807
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2667(4) 0.64639(11) 0.47278(4) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.1951(4) 0.63311(14) 0.50942(4) 0.0265(3) Uani 1 1 d . . . . .
H2 H 0.264676 0.560280 0.521729 0.032 Uiso 1 1 calc R . . . .
C3 C 0.0253(4) 0.71941(14) 0.53046(4) 0.0268(3) Uani 1 1 d . . . . .
H3 H -0.015310 0.706945 0.556603 0.032 Uiso 1 1 calc R . . . .
C4 C -0.0838(4) 0.82464(14) 0.51224(4) 0.0265(3) Uani 1 1 d . . . . .
H4 H -0.207745 0.884654 0.525537 0.032 Uiso 1 1 calc R . . . .
C5 C -0.0094(4) 0.84091(13) 0.47441(4) 0.0241(3) Uani 1 1 d . . . . .
H5 H -0.080073 0.912501 0.461456 0.029 Uiso 1 1 calc R . . . .
C6 C 0.1705(4) 0.75083(13) 0.45561(4) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.2633(4) 0.76620(13) 0.41525(4) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.2392(4) 0.88791(13) 0.39687(4) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.0880(4) 0.89944(14) 0.36061(4) 0.0265(3) Uani 1 1 d . . . . .
H9 H -0.013902 0.831518 0.348097 0.032 Uiso 1 1 calc R . . . .
C10 C 0.0885(4) 1.01127(15) 0.34315(4) 0.0303(4) Uani 1 1 d . . . . .
H10 H -0.014912 1.021662 0.318552 0.036 Uiso 1 1 calc R . . . .
C11 C 0.2426(4) 1.10792(15) 0.36215(5) 0.0303(4) Uani 1 1 d . . . . .
H11 H 0.250314 1.185562 0.350721 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3852(4) 1.08866(14) 0.39822(4) 0.0271(3) Uani 1 1 d . . . . .
H12 H 0.489590 1.155272 0.411188 0.033 Uiso 1 1 calc R . . . .
N13 N 0.3841(4) 0.98135(11) 0.41586(4) 0.0243(3) Uani 1 1 d . . . . .
N14 N 0.3717(4) 0.68446(11) 0.39232(3) 0.0250(3) Uani 1 1 d . . . . .
N15 N 0.4127(4) 0.56769(12) 0.40363(4) 0.0286(3) Uani 1 1 d . . . . .
H15 H 0.374(5) 0.5496(18) 0.4282(6) 0.033(5) Uiso 1 1 d . . . . .
C16 C 0.5519(4) 0.48490(14) 0.37877(4) 0.0265(3) Uani 1 1 d . . . . .
O17 O 0.5956(4) 0.38011(10) 0.38832(3) 0.0345(3) Uani 1 1 d . . . . .
N18 N 0.6288(4) 0.53479(12) 0.34479(4) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.589(6) 0.612(2) 0.3428(6) 0.034(5) Uiso 1 1 d . . . . .
C19 C 0.7676(4) 0.47929(14) 0.31288(4) 0.0250(3) Uani 1 1 d . . . . .
C20 C 0.8519(5) 0.55453(15) 0.28282(5) 0.0300(3) Uani 1 1 d . . . . .
H20 H 0.818744 0.639302 0.284874 0.036 Uiso 1 1 calc R . . . .
C21 C 0.9837(5) 0.50651(16) 0.24999(5) 0.0324(4) Uani 1 1 d . . . . .
H21 H 1.037892 0.558415 0.229554 0.039 Uiso 1 1 calc R . . . .
C22 C 1.0369(5) 0.38312(16) 0.24677(5) 0.0333(4) Uani 1 1 d . . . . .
H22 H 1.127468 0.349988 0.224283 0.040 Uiso 1 1 calc R . . . .
C23 C 0.9559(5) 0.30883(15) 0.27687(5) 0.0329(4) Uani 1 1 d . . . . .
H23 H 0.992968 0.224247 0.274844 0.039 Uiso 1 1 calc R . . . .
C24 C 0.8218(4) 0.35541(14) 0.30992(4) 0.0282(3) Uani 1 1 d . . . . .
H24 H 0.767700 0.303235 0.330295 0.034 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C6 117.71(13) . . ?
N1 C2 H2 118.1 . . ?
N1 C2 C3 123.81(14) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.08(14) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.09(14) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.09(14) . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 122.14(13) . . ?
N1 C6 C7 117.12(13) . . ?
C5 C6 C7 120.74(13) . . ?
C6 C7 C8 120.26(12) . . ?
N14 C7 C6 127.66(13) . . ?
N14 C7 C8 112.08(12) . . ?
C9 C8 C7 119.88(13) . . ?
N13 C8 C7 117.24(13) . . ?
N13 C8 C9 122.78(13) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 118.96(15) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.85(15) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.42(14) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 118.1 . . ?
N13 C12 C11 123.73(15) . . ?
N13 C12 H12 118.1 . . ?
C12 N13 C8 117.24(13) . . ?
C7 N14 N15 121.23(13) . . ?
N14 N15 H15 118.0(13) . . ?
N14 N15 C16 119.04(13) . . ?
C16 N15 H15 122.5(13) . . ?
O17 C16 N15 120.45(14) . . ?
O17 C16 N18 126.72(14) . . ?
N18 C16 N15 112.82(13) . . ?
C16 N18 H18 115.2(14) . . ?
C16 N18 C19 128.91(13) . . ?
C19 N18 H18 115.9(14) . . ?
C20 C19 N18 116.89(14) . . ?
C24 C19 N18 123.61(14) . . ?
C24 C19 C20 119.50(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.45(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.37(15) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.98(15) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.41(16) . . ?
C24 C23 H23 119.3 . . ?
C19 C24 H24 120.4 . . ?
C23 C24 C19 119.29(15) . . ?
C23 C24 H24 120.4 . . ?
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
N1 C2 1.338(2) . ?
N1 C6 1.3512(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.488(2) . ?
C7 C8 1.4966(19) . ?
C7 N14 1.2916(19) . ?
C8 C9 1.394(2) . ?
C8 N13 1.344(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C12 N13 1.3408(19) . ?
N14 N15 1.3603(18) . ?
N15 H15 0.91(2) . ?
N15 C16 1.387(2) . ?
C16 O17 1.2180(19) . ?
C16 N18 1.361(2) . ?
N18 H18 0.87(2) . ?
N18 C19 1.402(2) . ?
C19 C20 1.395(2) . ?
C19 C24 1.391(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9500 . ?
