#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151889.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_7151889
loop_
_publ_author_name
'Chevallier, Floris'
'Halauko, Yury S.'
'Pecceu, Christelle'
'Nassar, Ibrahim F.'
'Dam, To Uyen'
'Roisnel, Thierry'
'Matulis, Vadim E.'
'Ivashkevich, Oleg A.'
'Mongin, Florence'
_publ_section_title
;
 N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative
 metallation using a combination of lithium and zinc amides
;
_journal_issue                   12
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4671
_journal_paper_doi               10.1039/c1ob05267e
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H10 N4'
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2011-02-16T11:29:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.060(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.745(4)
_cell_length_b                   12.472(6)
_cell_length_c                   10.787(5)
_cell_measurement_reflns_used    710
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      2.5
_cell_measurement_wavelength     0.71073
_cell_volume                     1041.3(9)
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999),
CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_unetI/netI     0.1707
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2360
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.09
_refine_ls_extinction_coef       0.055(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0797P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                1062
_reflns_number_total             2360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05267e.txt
_cod_data_source_block           1j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151889
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.2220(4) 0.2900(3) 0.4313(3) 0.0286(8) Uani 1 1 d . . .
H1 H 0.2268 0.2464 0.3593 0.034 Uiso 1 1 calc R . .
C2 C 0.2405(4) 0.3988(3) 0.4362(3) 0.0330(9) Uani 1 1 d . . .
H2 H 0.2604 0.4463 0.3693 0.04 Uiso 1 1 calc R . .
C3 C 0.2238(4) 0.4249(2) 0.5619(3) 0.0289(8) Uani 1 1 d . . .
H3 H 0.2318 0.4958 0.5937 0.035 Uiso 1 1 calc R . .
N4 N 0.1956(3) 0.33880(19) 0.6313(2) 0.0255(7) Uani 1 1 d . . .
N5 N 0.1954(3) 0.25578(19) 0.5481(2) 0.0237(6) Uani 1 1 d . . .
C6 C 0.1659(4) 0.1483(2) 0.5887(3) 0.0231(7) Uani 1 1 d . . .
C7 C 0.3003(4) 0.0749(2) 0.5802(3) 0.0256(8) Uani 1 1 d . . .
H7 H 0.4081 0.0969 0.5492 0.031 Uiso 1 1 calc R . .
C8 C 0.2767(4) -0.0305(3) 0.6169(3) 0.0290(8) Uani 1 1 d . . .
H8 H 0.368 -0.0809 0.6111 0.035 Uiso 1 1 calc R . .
C9 C 0.1204(4) -0.0617(3) 0.6618(3) 0.0276(8) Uani 1 1 d . . .
H9 H 0.1049 -0.1336 0.6884 0.033 Uiso 1 1 calc R . .
C10 C -0.0148(4) 0.0109(3) 0.6687(3) 0.0264(8) Uani 1 1 d . . .
H10 H -0.1225 -0.0116 0.6992 0.032 Uiso 1 1 calc R . .
C11 C 0.0070(4) 0.1163(2) 0.6314(3) 0.0228(7) Uani 1 1 d . . .
N12 N -0.1360(3) 0.18716(19) 0.6393(2) 0.0244(7) Uani 1 1 d . . .
N13 N -0.2515(3) 0.1692(2) 0.7303(2) 0.0310(7) Uani 1 1 d . . .
C14 C -0.3785(4) 0.2377(3) 0.7038(3) 0.0343(9) Uani 1 1 d . . .
H14 H -0.4785 0.2448 0.7515 0.041 Uiso 1 1 calc R . .
C15 C -0.3486(4) 0.2986(3) 0.5974(3) 0.0323(9) Uani 1 1 d . . .
H15 H -0.4211 0.3521 0.5604 0.039 Uiso 1 1 calc R . .
C16 C -0.1937(4) 0.2642(2) 0.5591(3) 0.0284(8) Uani 1 1 d . . .
H16 H -0.1356 0.2895 0.4887 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
N5 C1 C2 107.3(3) . . ?
N5 C1 H1 126.4 . . ?
C2 C1 H1 126.4 . . ?
C1 C2 C3 104.7(3) . . ?
C1 C2 H2 127.7 . . ?
C3 C2 H2 127.7 . . ?
N4 C3 C2 112.3(3) . . ?
N4 C3 H3 123.9 . . ?
C2 C3 H3 123.9 . . ?
C3 N4 N5 103.8(3) . . ?
C1 N5 N4 112.0(2) . . ?
C1 N5 C6 127.7(3) . . ?
N4 N5 C6 120.3(2) . . ?
C11 C6 C7 120.5(3) . . ?
C11 C6 N5 121.6(3) . . ?
C7 C6 N5 117.9(3) . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C6 119.2(3) . . ?
C10 C11 N12 117.9(3) . . ?
C6 C11 N12 122.9(3) . . ?
C16 N12 N13 111.3(2) . . ?
C16 N12 C11 129.8(3) . . ?
N13 N12 C11 118.1(2) . . ?
C14 N13 N12 103.8(3) . . ?
N13 C14 C15 112.5(3) . . ?
N13 C14 H14 123.7 . . ?
C15 C14 H14 123.7 . . ?
C16 C15 C14 104.6(3) . . ?
C16 C15 H15 127.7 . . ?
C14 C15 H15 127.7 . . ?
C15 C16 N12 107.8(3) . . ?
C15 C16 H16 126.1 . . ?
N12 C16 H16 126.1 . . ?
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
C1 N5 1.353(4) . ?
C1 C2 1.366(4) . ?
C1 H1 0.95 . ?
C2 C3 1.405(4) . ?
C2 H2 0.95 . ?
C3 N4 1.331(4) . ?
C3 H3 0.95 . ?
N4 N5 1.370(3) . ?
N5 C6 1.431(4) . ?
C6 C11 1.388(4) . ?
C6 C7 1.392(4) . ?
C7 C8 1.387(4) . ?
C7 H7 0.95 . ?
C8 C9 1.376(4) . ?
C8 H8 0.95 . ?
C9 C10 1.389(4) . ?
C9 H9 0.95 . ?
C10 C11 1.387(4) . ?
C10 H10 0.95 . ?
C11 N12 1.422(4) . ?
N12 C16 1.358(4) . ?
N12 N13 1.370(3) . ?
N13 C14 1.326(4) . ?
C14 C15 1.402(4) . ?
C14 H14 0.95 . ?
C15 C16 1.353(4) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
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
N5 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 N4 -0.4(4) . . . . ?
C2 C3 N4 N5 0.4(4) . . . . ?
C2 C1 N5 N4 0.0(3) . . . . ?
C2 C1 N5 C6 178.8(3) . . . . ?
C3 N4 N5 C1 -0.3(4) . . . . ?
C3 N4 N5 C6 -179.1(3) . . . . ?
C1 N5 C6 C11 -111.4(4) . . . . ?
N4 N5 C6 C11 67.3(4) . . . . ?
C1 N5 C6 C7 66.5(4) . . . . ?
N4 N5 C6 C7 -114.9(3) . . . . ?
C11 C6 C7 C8 -1.3(4) . . . . ?
N5 C6 C7 C8 -179.2(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C6 -0.8(4) . . . . ?
C9 C10 C11 N12 179.4(3) . . . . ?
C7 C6 C11 C10 1.8(4) . . . . ?
N5 C6 C11 C10 179.6(3) . . . . ?
C7 C6 C11 N12 -178.5(3) . . . . ?
N5 C6 C11 N12 -0.7(4) . . . . ?
C10 C11 N12 C16 -139.4(3) . . . . ?
C6 C11 N12 C16 40.9(5) . . . . ?
C10 C11 N12 N13 30.2(4) . . . . ?
C6 C11 N12 N13 -149.5(3) . . . . ?
C16 N12 N13 C14 -0.6(3) . . . . ?
C11 N12 N13 C14 -172.1(3) . . . . ?
N12 N13 C14 C15 0.6(3) . . . . ?
N13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 N12 -0.1(4) . . . . ?
N13 N12 C16 C15 0.4(3) . . . . ?
C11 N12 C16 C15 170.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26997466
2 PubChem 69007263
