#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151884.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_7151884
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         'C11 H12 I N3'
_chemical_formula_sum            'C11 H12 I N3'
_chemical_formula_weight         313.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_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             2010-02-24T10:53:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 111.017(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3777(3)
_cell_length_b                   19.1576(9)
_cell_length_c                   8.7098(4)
_cell_measurement_reflns_used    6782
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.13
_cell_measurement_wavelength     0.71073
_cell_volume                     1149.14(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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9641
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  0.437
_exptl_absorpt_correction_T_min  0.257
_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    1.81
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.8
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.21
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0221
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0154P)²+1.7898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0596
_reflns_number_gt                2432
_reflns_number_total             2611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05267e.txt
_cod_data_source_block           2b
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151884
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
I1 I 0.31639(3) 0.167336(10) 0.03136(2) 0.01987(7) Uani 1 1 d . . .
C1 C 0.0569(4) 0.18045(15) 0.0701(4) 0.0190(6) Uani 1 1 d . . .
C2 C 0.0231(5) 0.21787(16) 0.1926(4) 0.0240(6) Uani 1 1 d . . .
H2 H 0.1123 0.2457 0.276 0.029 Uiso 1 1 calc R . .
C3 C -0.1721(5) 0.20553(16) 0.1657(4) 0.0251(7) Uani 1 1 d . . .
H3 H -0.238 0.2251 0.2313 0.03 Uiso 1 1 calc R . .
N4 N -0.2569(4) 0.16323(13) 0.0377(3) 0.0234(5) Uani 1 1 d . . .
N5 N -0.1119(3) 0.14798(13) -0.0211(3) 0.0184(5) Uani 1 1 d . . .
C6 C -0.1512(4) 0.10413(14) -0.1628(3) 0.0164(5) Uani 1 1 d . . .
C7 C -0.2048(4) 0.03517(15) -0.1578(3) 0.0181(6) Uani 1 1 d . . .
H7 H -0.2144 0.0167 -0.0598 0.022 Uiso 1 1 calc R . .
C8 C -0.2444(4) -0.00696(15) -0.2951(3) 0.0186(6) Uani 1 1 d . . .
H8 H -0.2814 -0.0542 -0.2903 0.022 Uiso 1 1 calc R . .
C9 C -0.2308(4) 0.01907(15) -0.4418(3) 0.0171(6) Uani 1 1 d . . .
C10 C -0.1767(4) 0.08924(15) -0.4444(3) 0.0190(6) Uani 1 1 d . . .
H10 H -0.167 0.1082 -0.5419 0.023 Uiso 1 1 calc R . .
C11 C -0.1373(4) 0.13098(15) -0.3068(3) 0.0192(6) Uani 1 1 d . . .
H11 H -0.1005 0.1783 -0.3105 0.023 Uiso 1 1 calc R . .
N12 N -0.2652(4) -0.02345(13) -0.5764(3) 0.0215(5) Uani 1 1 d . . .
C13 C -0.3124(5) -0.09629(16) -0.5700(4) 0.0245(6) Uani 1 1 d . . .
H13A H -0.2123 -0.1186 -0.4766 0.037 Uiso 1 1 calc R . .
H13B H -0.3186 -0.1193 -0.6723 0.037 Uiso 1 1 calc R . .
H13C H -0.4385 -0.1003 -0.5569 0.037 Uiso 1 1 calc R . .
C14 C -0.2760(5) 0.00600(17) -0.7333(4) 0.0253(6) Uani 1 1 d . . .
H14A H -0.3673 0.0452 -0.7614 0.038 Uiso 1 1 calc R . .
H14B H -0.3208 -0.0298 -0.819 0.038 Uiso 1 1 calc R . .
H14C H -0.1471 0.0225 -0.7253 0.038 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'
I I -0.4742 1.8119 '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 107.8(3) . . ?
N5 C1 I1 123.6(2) . . ?
C2 C1 I1 128.5(2) . . ?
C1 C2 C3 104.2(3) . . ?
C1 C2 H2 127.9 . . ?
C3 C2 H2 127.9 . . ?
N4 C3 C2 112.9(3) . . ?
N4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3 N4 N5 104.2(2) . . ?
C1 N5 N4 110.9(2) . . ?
C1 N5 C6 129.0(2) . . ?
N4 N5 C6 120.1(2) . . ?
C7 C6 C11 119.6(3) . . ?
C7 C6 N5 120.3(2) . . ?
C11 C6 N5 120.1(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
N12 C9 C10 121.4(3) . . ?
N12 C9 C8 120.8(3) . . ?
C10 C9 C8 117.8(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C9 N12 C13 120.9(2) . . ?
C9 N12 C14 120.2(2) . . ?
C13 N12 C14 118.6(2) . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
I1 C1 2.075(3) . ?
C1 N5 1.364(4) . ?
C1 C2 1.380(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.95 . ?
C3 N4 1.338(4) . ?
C3 H3 0.95 . ?
N4 N5 1.373(3) . ?
N5 C6 1.434(3) . ?
C6 C7 1.384(4) . ?
C6 C11 1.393(4) . ?
C7 C8 1.384(4) . ?
C7 H7 0.95 . ?
C8 C9 1.409(4) . ?
C8 H8 0.95 . ?
C9 N12 1.374(4) . ?
C9 C10 1.405(4) . ?
C10 C11 1.382(4) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
N12 C13 1.444(4) . ?
N12 C14 1.454(4) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
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 -0.4(3) . . . . ?
I1 C1 C2 C3 -176.6(2) . . . . ?
C1 C2 C3 N4 0.5(4) . . . . ?
C2 C3 N4 N5 -0.4(4) . . . . ?
C2 C1 N5 N4 0.2(3) . . . . ?
I1 C1 N5 N4 176.61(19) . . . . ?
C2 C1 N5 C6 179.0(3) . . . . ?
I1 C1 N5 C6 -4.6(4) . . . . ?
C3 N4 N5 C1 0.1(3) . . . . ?
C3 N4 N5 C6 -178.8(3) . . . . ?
C1 N5 C6 C7 117.6(3) . . . . ?
N4 N5 C6 C7 -63.7(4) . . . . ?
C1 N5 C6 C11 -62.9(4) . . . . ?
N4 N5 C6 C11 115.7(3) . . . . ?
C11 C6 C7 C8 0.0(4) . . . . ?
N5 C6 C7 C8 179.4(3) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 N12 178.2(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
N12 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C6 -0.2(4) . . . . ?
C7 C6 C11 C10 0.0(4) . . . . ?
N5 C6 C11 C10 -179.4(3) . . . . ?
C10 C9 N12 C13 177.3(3) . . . . ?
C8 C9 N12 C13 -1.3(4) . . . . ?
C10 C9 N12 C14 -9.6(4) . . . . ?
C8 C9 N12 C14 171.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26997470
2 PubChem 53309903
