#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151888.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_7151888
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         'C8 H7 N3'
_chemical_formula_sum            'C8 H7 N3'
_chemical_formula_weight         145.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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             2011-02-16T11:16:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.229(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.299(3)
_cell_length_b                   4.2309(9)
_cell_length_c                   14.743(3)
_cell_measurement_reflns_used    2131
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.76
_cell_measurement_wavelength     0.71073
_cell_volume                     704.8(3)
_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 0.986
_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  0.036
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.616
_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    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.4046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                1174
_reflns_number_total             1606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05267e.txt
_cod_data_source_block           1o
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7151888
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06691(17) 0.1212(5) 0.34996(13) 0.0291(5) Uani 1 1 d . . .
H1 H -0.016 0.1488 0.3422 0.035 Uiso 1 1 calc R . .
C2 C 0.12128(18) -0.0563(6) 0.41548(14) 0.0325(5) Uani 1 1 d . . .
H2 H 0.0851 -0.1764 0.4622 0.039 Uiso 1 1 calc R . .
C3 C 0.24284(17) -0.0209(6) 0.39816(13) 0.0316(5) Uani 1 1 d . . .
H3 H 0.3033 -0.1188 0.4332 0.038 Uiso 1 1 calc R . .
N4 N 0.26350(13) 0.1643(5) 0.32753(11) 0.0290(4) Uani 1 1 d . . .
N5 N 0.15328(13) 0.2510(4) 0.29784(10) 0.0235(4) Uani 1 1 d . . .
C6 C 0.14162(15) 0.4494(5) 0.22105(12) 0.0210(4) Uani 1 1 d . . .
C7 C 0.02939(15) 0.5301(5) 0.18775(13) 0.0274(5) Uani 1 1 d . . .
H7 H -0.0383 0.4533 0.2188 0.033 Uiso 1 1 calc R . .
N8 N 0.01322(13) 0.7098(5) 0.11449(11) 0.0326(5) Uani 1 1 d . . .
C9 C 0.10957(16) 0.8168(5) 0.07168(13) 0.0286(5) Uani 1 1 d . . .
H9 H 0.0993 0.9419 0.0187 0.034 Uiso 1 1 calc R . .
C10 C 0.22377(15) 0.7527(5) 0.10138(13) 0.0258(5) Uani 1 1 d . . .
H10 H 0.2899 0.837 0.07 0.031 Uiso 1 1 calc R . .
C11 C 0.24003(14) 0.5663(5) 0.17650(12) 0.0242(5) Uani 1 1 d . . .
H11 H 0.3175 0.5182 0.1976 0.029 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0205(9) 0.0318(14) 0.0352(10) -0.0016(9) 0.0068(7) -0.0027(8)
C2 0.0331(11) 0.0311(14) 0.0335(10) 0.0002(9) 0.0067(8) -0.0008(9)
C3 0.0281(10) 0.0333(14) 0.0335(10) -0.0004(9) -0.0026(8) 0.0031(9)
N4 0.0164(7) 0.0361(12) 0.0346(9) 0.0005(8) -0.0024(6) 0.0034(7)
N5 0.0138(7) 0.0257(10) 0.0308(8) -0.0025(7) 0.0018(6) 0.0009(7)
C6 0.0140(8) 0.0219(11) 0.0273(9) -0.0041(8) 0.0016(6) 0.0019(7)
C7 0.0115(8) 0.0326(13) 0.0382(10) 0.0019(9) 0.0035(7) -0.0023(8)
N8 0.0122(7) 0.0456(13) 0.0400(10) 0.0067(8) 0.0012(6) 0.0010(7)
C9 0.0159(9) 0.0374(14) 0.0326(10) 0.0034(9) 0.0015(7) 0.0020(8)
C10 0.0126(8) 0.0314(13) 0.0335(10) -0.0012(8) 0.0051(7) 0.0002(8)
C11 0.0099(7) 0.0278(12) 0.0349(10) -0.0029(8) 0.0009(7) 0.0006(7)
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 107.42(17) . . ?
N5 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
C1 C2 C3 104.46(18) . . ?
C1 C2 H2 127.8 . . ?
C3 C2 H2 127.8 . . ?
N4 C3 C2 112.40(18) . . ?
N4 C3 H3 123.8 . . ?
C2 C3 H3 123.8 . . ?
C3 N4 N5 104.29(15) . . ?
C1 N5 N4 111.42(16) . . ?
C1 N5 C6 128.81(16) . . ?
N4 N5 C6 119.77(14) . . ?
C11 C6 C7 118.31(18) . . ?
C11 C6 N5 121.26(16) . . ?
C7 C6 N5 120.43(16) . . ?
N8 C7 C6 122.98(17) . . ?
N8 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C7 N8 C9 117.74(16) . . ?
N8 C9 C10 122.81(19) . . ?
N8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 119.25(17) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C6 118.89(16) . . ?
C10 C11 H11 120.6 . . ?
C6 C11 H11 120.6 . . ?
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 1.360(2) . ?
C1 C2 1.367(3) . ?
C1 H1 0.95 . ?
C2 C3 1.406(3) . ?
C2 H2 0.95 . ?
C3 N4 1.325(3) . ?
C3 H3 0.95 . ?
N4 N5 1.368(2) . ?
N5 C6 1.415(2) . ?
C6 C11 1.385(2) . ?
C6 C7 1.400(2) . ?
C7 N8 1.333(3) . ?
C7 H7 0.95 . ?
N8 C9 1.339(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.95 . ?
C10 C11 1.371(3) . ?
C10 H10 0.95 . ?
C11 H11 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 0.1(2) . . . . ?
C1 C2 C3 N4 0.1(3) . . . . ?
C2 C3 N4 N5 -0.2(2) . . . . ?
C2 C1 N5 N4 -0.2(2) . . . . ?
C2 C1 N5 C6 179.13(19) . . . . ?
C3 N4 N5 C1 0.2(2) . . . . ?
C3 N4 N5 C6 -179.14(17) . . . . ?
C1 N5 C6 C11 178.80(19) . . . . ?
N4 N5 C6 C11 -1.9(3) . . . . ?
C1 N5 C6 C7 -1.8(3) . . . . ?
N4 N5 C6 C7 177.52(17) . . . . ?
C11 C6 C7 N8 1.1(3) . . . . ?
N5 C6 C7 N8 -178.37(18) . . . . ?
C6 C7 N8 C9 -0.2(3) . . . . ?
C7 N8 C9 C10 -1.1(3) . . . . ?
N8 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
N5 C6 C11 C10 178.76(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9553481
2 PubChem 11378567
