#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/22/7052218.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_7052218
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            4-((3,5-dimethylpyrazol-1-yl)methyl)benzamide
_chemical_name_systematic
;
4-[(3,5-dimethylpyrazol-1-yl)methyl]benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.621(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4005(7)
_cell_length_b                   8.0671(7)
_cell_length_c                   18.0477(18)
_cell_measurement_reflns_used    2149
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.25
_cell_volume                     1193.50(19)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0919
_diffrn_reflns_av_sigmaI/netI    0.0890
_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       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8390
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0491
_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)+(0.0650P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1646
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715610c.txt
_cod_data_source_block           8
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               7052218
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.21703(18) 0.6793(2) 0.11285(9) 0.0310(4) Uani 1 1 d . . .
C12 C 0.3110(2) 0.7028(2) 0.18532(10) 0.0360(4) Uani 1 1 d . . .
H12 H 0.3089 0.8063 0.2101 0.043 Uiso 1 1 calc R . .
C13 C 0.4078(2) 0.5754(2) 0.22152(9) 0.0353(4) Uani 1 1 d . . .
H13 H 0.4700 0.5915 0.2717 0.042 Uiso 1 1 calc R . .
C14 C 0.41517(19) 0.4260(2) 0.18609(9) 0.0320(4) Uani 1 1 d . . .
C15 C 0.3196(2) 0.4029(2) 0.11392(10) 0.0401(5) Uani 1 1 d . . .
H15 H 0.3231 0.2999 0.0889 0.048 Uiso 1 1 calc R . .
C16 C 0.2199(2) 0.5269(2) 0.07806(10) 0.0382(5) Uani 1 1 d . . .
H16 H 0.1526 0.5080 0.0292 0.046 Uiso 1 1 calc R . .
C17 C 0.11795(19) 0.8153(2) 0.06987(10) 0.0356(4) Uani 1 1 d . . .
N17 N 0.1721(2) 0.9681(2) 0.08575(9) 0.0401(4) Uani 1 1 d . . .
H17A H 0.119(2) 1.046(3) 0.0601(11) 0.048 Uiso 1 1 d . . .
H17B H 0.273(2) 0.991(2) 0.1149(11) 0.048 Uiso 1 1 d . . .
O17 O -0.00548(14) 0.78419(17) 0.02102(7) 0.0462(4) Uani 1 1 d . . .
C18 C 0.5249(2) 0.2908(2) 0.22583(10) 0.0410(5) Uani 1 1 d . . .
H18A H 0.6115 0.3414 0.2655 0.049 Uiso 1 1 calc R . .
H18B H 0.4604 0.2161 0.2515 0.049 Uiso 1 1 calc R . .
N21 N 0.60028(17) 0.19388(19) 0.17564(8) 0.0354(4) Uani 1 1 d . . .
N22 N 0.53928(17) 0.04067(19) 0.15246(8) 0.0367(4) Uani 1 1 d . . .
C23 C 0.6341(2) -0.0150(2) 0.10780(9) 0.0350(4) Uani 1 1 d . . .
C24 C 0.7526(2) 0.1018(3) 0.10208(10) 0.0389(5) Uani 1 1 d . . .
H24 H 0.8346 0.0914 0.0735 0.047 Uiso 1 1 calc R . .
C25 C 0.7285(2) 0.2339(2) 0.14533(9) 0.0367(5) Uani 1 1 d . . .
C26 C 0.6058(2) -0.1797(3) 0.07050(11) 0.0458(5) Uani 1 1 d . . .
H26A H 0.5623 -0.2562 0.1033 0.069 Uiso 1 1 calc R . .
H26B H 0.7091 -0.2231 0.0617 0.069 Uiso 1 1 calc R . .
H26C H 0.5275 -0.1685 0.0218 0.069 Uiso 1 1 calc R . .
C27 C 0.8155(2) 0.3951(3) 0.16104(12) 0.0558(6) Uani 1 1 d . . .
H27A H 0.8579 0.4071 0.2158 0.084 Uiso 1 1 calc R . .
H27B H 0.7397 0.4860 0.1427 0.084 Uiso 1 1 calc R . .
H27C H 0.9062 0.3985 0.1349 0.084 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 119.16(16) . . ?
C16 C11 C17 118.79(15) . . ?
C12 C11 C17 122.00(16) . . ?
C13 C12 C11 119.98(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.96(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.69(16) . . ?
C13 C14 C18 119.97(14) . . ?
C15 C14 C18 121.34(16) . . ?
C16 C15 C14 120.95(17) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 120.20(16) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O17 C17 N17 122.71(17) . . ?
O17 C17 C11 120.72(17) . . ?
N17 C17 C11 116.55(15) . . ?
C17 N17 H17A 117.4(14) . . ?
C17 N17 H17B 123.2(12) . . ?
H17A N17 H17B 118.1(19) . . ?
N21 C18 C14 113.61(14) . . ?
N21 C18 H18A 108.8 . . ?
C14 C18 H18A 108.8 . . ?
N21 C18 H18B 108.8 . . ?
C14 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C25 N21 N22 111.77(15) . . ?
C25 N21 C18 128.54(17) . . ?
N22 N21 C18 119.68(15) . . ?
C23 N22 N21 104.86(14) . . ?
N22 C23 C24 110.49(17) . . ?
N22 C23 C26 121.28(17) . . ?
C24 C23 C26 128.22(18) . . ?
C25 C24 C23 106.81(16) . . ?
C25 C24 H24 126.6 . . ?
C23 C24 H24 126.6 . . ?
N21 C25 C24 106.07(16) . . ?
N21 C25 C27 122.28(18) . . ?
C24 C25 C27 131.65(18) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 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 1.383(2) . ?
C11 C12 1.385(2) . ?
C11 C17 1.488(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 C18 1.504(2) . ?
C15 C16 1.373(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2311(19) . ?
C17 N17 1.324(2) . ?
N17 H17A 0.85(2) . ?
N17 H17B 0.91(2) . ?
C18 N21 1.443(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N21 C25 1.349(2) . ?
N21 N22 1.368(2) . ?
N22 C23 1.329(2) . ?
C23 C24 1.390(3) . ?
C23 C26 1.485(3) . ?
C24 C25 1.362(3) . ?
C24 H24 0.9500 . ?
C25 C27 1.489(3) . ?
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 0.85(2) 2.08(2) 2.913(2) 168.3(19) 3_575
N17 H17B N22 0.91(2) 2.23(2) 3.112(2) 162.7(17) 1_565
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 C12 C13 0.9(3) . . . . ?
C17 C11 C12 C13 -176.60(16) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 -2.0(3) . . . . ?
C12 C13 C14 C18 178.31(16) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C18 C14 C15 C16 -179.96(18) . . . . ?
C14 C15 C16 C11 1.9(3) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C17 C11 C16 C15 175.05(17) . . . . ?
C16 C11 C17 O17 29.4(3) . . . . ?
C12 C11 C17 O17 -153.13(18) . . . . ?
C16 C11 C17 N17 -148.97(17) . . . . ?
C12 C11 C17 N17 28.5(2) . . . . ?
C13 C14 C18 N21 -143.63(17) . . . . ?
C15 C14 C18 N21 36.7(2) . . . . ?
C14 C18 N21 C25 77.4(2) . . . . ?
C14 C18 N21 N22 -101.65(18) . . . . ?
C25 N21 N22 C23 0.88(17) . . . . ?
C18 N21 N22 C23 -179.88(14) . . . . ?
N21 N22 C23 C24 -0.58(18) . . . . ?
N21 N22 C23 C26 -179.55(14) . . . . ?
N22 C23 C24 C25 0.09(19) . . . . ?
C26 C23 C24 C25 178.97(16) . . . . ?
N22 N21 C25 C24 -0.84(18) . . . . ?
C18 N21 C25 C24 -179.98(15) . . . . ?
N22 N21 C25 C27 179.29(15) . . . . ?
C18 N21 C25 C27 0.1(3) . . . . ?
C23 C24 C25 N21 0.44(18) . . . . ?
C23 C24 C25 C27 -179.70(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119837
2 PubChem 21976451
