#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/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 _chemical_name_systematic ; ? ; _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/[\s^2^(Fo^2^)+(0.0632P)^2^+0.4046P] where P=(Fo^2^+2Fc^2^)/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