#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/22/7052221.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_7052221
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Scott, Benjamin M. T.'
'Desper, John'
_publ_section_title
;
 How robust is the hydrogen-bonded amide ‘ladder’ motif?
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2044
_journal_paper_doi               10.1039/b715610c
_journal_volume                  31
_journal_year                    2007
_chemical_formula_moiety         'C13 H15 N3 O'
_chemical_formula_sum            'C13 H15 N3 O'
_chemical_formula_weight         229.28
_chemical_name_common
'BS-3-92-4 3-((3,5-dimethylpyrazol-1-yl)methyl)benzamide'
_chemical_name_systematic
;
BS-3-92-4 3-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.253(2)
_cell_angle_beta                 106.060(2)
_cell_angle_gamma                109.335(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0162(4)
_cell_length_b                   8.0603(4)
_cell_length_c                   10.4542(5)
_cell_measurement_reflns_used    9065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.45
_cell_measurement_theta_min      2.75
_cell_volume                     594.57(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21375
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0434
_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/[σ²(Fo²)+(0.0700P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                3010
_reflns_number_total             3757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715610c.txt
_cod_data_source_block           11
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7052221
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.50776(13) 0.29422(13) 0.41569(9) 0.01634(19) Uani 1 1 d . . .
C17 C 0.71498(14) 0.36120(14) 0.44063(10) 0.0191(2) Uani 1 1 d . . .
N17 N 0.82663(12) 0.35198(13) 0.55890(9) 0.02161(19) Uani 1 1 d . . .
H17A H 0.953(2) 0.4118(18) 0.5791(14) 0.026 Uiso 1 1 d . . .
H17B H 0.7841(19) 0.3334(18) 0.6313(14) 0.026 Uiso 1 1 d . . .
O17 O 0.77660(11) 0.41894(13) 0.35158(8) 0.0295(2) Uani 1 1 d . . .
C12 C 0.39548(13) 0.33393(13) 0.30537(10) 0.01725(19) Uani 1 1 d . . .
H12 H 0.4519 0.4025 0.2502 0.021 Uiso 1 1 calc R . .
C13 C 0.20265(13) 0.27440(13) 0.27557(10) 0.0182(2) Uani 1 1 d . . .
C14 C 0.12146(14) 0.17611(15) 0.35817(12) 0.0247(2) Uani 1 1 d . . .
H14 H -0.0102 0.1368 0.3396 0.030 Uiso 1 1 calc R . .
C15 C 0.23191(15) 0.13530(16) 0.46732(12) 0.0283(2) Uani 1 1 d . . .
H15 H 0.1753 0.0668 0.5225 0.034 Uiso 1 1 calc R . .
C16 C 0.42479(14) 0.19408(14) 0.49639(11) 0.0214(2) Uani 1 1 d . . .
H16 H 0.5000 0.1659 0.5713 0.026 Uiso 1 1 calc R . .
C18 C 0.07558(14) 0.31228(14) 0.15578(11) 0.0230(2) Uani 1 1 d . . .
H18A H 0.0060 0.1997 0.0819 0.028 Uiso 1 1 calc R . .
H18B H -0.0178 0.3467 0.1857 0.028 Uiso 1 1 calc R . .
N21 N 0.17553(12) 0.45476(11) 0.10082(9) 0.01901(18) Uani 1 1 d . . .
N22 N 0.24208(12) 0.62969(11) 0.17277(8) 0.01890(18) Uani 1 1 d . . .
C23 C 0.33358(14) 0.72696(14) 0.10142(10) 0.0188(2) Uani 1 1 d . . .
C24 C 0.32662(14) 0.61432(14) -0.01569(10) 0.0209(2) Uani 1 1 d . . .
H24 H 0.3811 0.6506 -0.0826 0.025 Uiso 1 1 calc R . .
C25 C 0.22440(14) 0.44036(14) -0.01330(10) 0.0202(2) Uani 1 1 d . . .
C26 C 0.16725(17) 0.26514(16) -0.11215(13) 0.0306(3) Uani 1 1 d . . .
H26A H 0.2161 0.1848 -0.0647 0.046 Uiso 1 1 calc R . .
H26B H 0.2182 0.2870 -0.1863 0.046 Uiso 1 1 calc R . .
H26C H 0.0298 0.2082 -0.1506 0.046 Uiso 1 1 calc R . .
C27 C 0.42308(17) 0.92828(15) 0.14995(12) 0.0280(2) Uani 1 1 d . . .
H27A H 0.3811 0.9678 0.2236 0.042 Uiso 1 1 calc R . .
H27B H 0.3868 0.9829 0.0736 0.042 Uiso 1 1 calc R . .
H27C H 0.5601 0.9664 0.1845 0.042 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 0.0033 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
C16 C11 C12 119.50(9) . . ?
C16 C11 C17 122.77(8) . . ?
C12 C11 C17 117.73(8) . . ?
O17 C17 N17 122.39(9) . . ?
O17 C17 C11 119.81(9) . . ?
N17 C17 C11 117.78(9) . . ?
C17 N17 H17A 116.3(8) . . ?
C17 N17 H17B 121.1(9) . . ?
H17A N17 H17B 117.4(12) . . ?
C13 C12 C11 120.74(9) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.23(9) . . ?
C12 C13 C18 122.40(9) . . ?
C14 C13 C18 118.37(9) . . ?
C15 C14 C13 120.33(9) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.31(10) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.89(9) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
N21 C18 C13 113.60(8) . . ?
N21 C18 H18A 108.8 . . ?
C13 C18 H18A 108.8 . . ?
N21 C18 H18B 108.8 . . ?
C13 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C25 N21 N22 112.15(8) . . ?
C25 N21 C18 129.00(9) . . ?
N22 N21 C18 118.75(8) . . ?
C23 N22 N21 105.03(8) . . ?
N22 C23 C24 110.89(9) . . ?
N22 C23 C27 119.76(9) . . ?
C24 C23 C27 129.35(10) . . ?
C25 C24 C23 105.73(9) . . ?
C25 C24 H24 127.1 . . ?
C23 C24 H24 127.1 . . ?
N21 C25 C24 106.19(9) . . ?
N21 C25 C26 123.53(10) . . ?
C24 C25 C26 130.26(10) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C11 C16 1.3902(13) . ?
C11 C12 1.3973(13) . ?
C11 C17 1.4999(13) . ?
C17 O17 1.2406(12) . ?
C17 N17 1.3380(13) . ?
N17 H17A 0.914(15) . ?
N17 H17B 0.921(14) . ?
C12 C13 1.3861(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3926(14) . ?
C13 C18 1.5152(13) . ?
C14 C15 1.3867(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3878(15) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 N21 1.4501(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N21 C25 1.3580(13) . ?
N21 N22 1.3604(12) . ?
N22 C23 1.3336(12) . ?
C23 C24 1.4051(14) . ?
C23 C27 1.4917(15) . ?
C24 C25 1.3775(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.4878(15) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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
N17 H17A O17 0.914(15) 2.002(15) 2.9033(12) 168.4(12) 2_766
N17 H17B N22 0.921(14) 2.110(14) 2.9997(12) 161.9(12) 2_666
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
C16 C11 C17 O17 166.24(10) . . . . ?
C12 C11 C17 O17 -13.09(15) . . . . ?
C16 C11 C17 N17 -12.26(15) . . . . ?
C12 C11 C17 N17 168.41(9) . . . . ?
C16 C11 C12 C13 -0.08(15) . . . . ?
C17 C11 C12 C13 179.27(9) . . . . ?
C11 C12 C13 C14 0.87(15) . . . . ?
C11 C12 C13 C18 -179.14(9) . . . . ?
C12 C13 C14 C15 -1.25(16) . . . . ?
C18 C13 C14 C15 178.76(10) . . . . ?
C13 C14 C15 C16 0.85(18) . . . . ?
C14 C15 C16 C11 -0.05(18) . . . . ?
C12 C11 C16 C15 -0.33(15) . . . . ?
C17 C11 C16 C15 -179.65(10) . . . . ?
C12 C13 C18 N21 -16.25(14) . . . . ?
C14 C13 C18 N21 163.75(9) . . . . ?
C13 C18 N21 C25 101.40(12) . . . . ?
C13 C18 N21 N22 -74.61(11) . . . . ?
C25 N21 N22 C23 0.42(10) . . . . ?
C18 N21 N22 C23 177.07(8) . . . . ?
N21 N22 C23 C24 -0.36(10) . . . . ?
N21 N22 C23 C27 178.87(9) . . . . ?
N22 C23 C24 C25 0.18(11) . . . . ?
C27 C23 C24 C25 -178.95(10) . . . . ?
N22 N21 C25 C24 -0.31(11) . . . . ?
C18 N21 C25 C24 -176.54(9) . . . . ?
N22 N21 C25 C26 -178.80(9) . . . . ?
C18 N21 C25 C26 4.98(15) . . . . ?
C23 C24 C25 N21 0.08(10) . . . . ?
C23 C24 C25 C26 178.43(10) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119834
2 PubChem 62045999
