#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:06:49 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/35/00/4350076.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_4350076
loop_
_publ_author_name
'Xiang, Shiqun'
'Zhang, Xiaofeng'
'Chen, Hui'
'Li, Yinghua'
'Fan, Weibin'
'Huang, Deguang'
_publ_section_title
;
 Copper(ii) facilitated decarboxylation for the construction of
 pyridyl--pyrazole skeletons
;
_journal_issue                   9
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              2359
_journal_paper_doi               10.1039/C9QI00599D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C10 H9 N3 O2'
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20
_chemical_name_common            3-Me-Py-Pz-COOH
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-10-12 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                92.199(6)
_cell_angle_beta                 98.583(9)
_cell_angle_gamma                99.681(8)
_cell_formula_units_Z            2
_cell_length_a                   5.7124(7)
_cell_length_b                   7.3887(5)
_cell_length_c                   11.5280(10)
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.3020
_cell_measurement_theta_min      6.1010
_cell_volume                     473.26(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3384
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.063
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.5088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1465
_reflns_number_total             1779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9qi00599d2.cif
_cod_data_source_block           full_CCDC5
_cod_database_code               4350076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.4236(4) 0.4037(3) 0.64316(19) 0.0228(5) Uani 1 1 d .
C2 C 0.3551(4) 0.3296(3) 0.75147(19) 0.0228(5) Uani 1 1 d .
C3 C 0.1196(4) 0.2547(3) 0.7680(2) 0.0249(5) Uani 1 1 d .
H3A H -0.0242 0.2432 0.7129 0.030 Uiso 1 1 calc R
C4 C 0.1440(4) 0.2024(3) 0.8808(2) 0.0247(5) Uani 1 1 d .
H4A H 0.0192 0.1451 0.9202 0.030 Uiso 1 1 calc R
C5 C 0.4918(4) 0.2254(3) 1.04287(19) 0.0214(5) Uani 1 1 d .
C6 C 0.7335(4) 0.2945(3) 1.0816(2) 0.0244(5) Uani 1 1 d .
H6A H 0.8321 0.3581 1.0314 0.029 Uiso 1 1 calc R
C7 C 0.8251(4) 0.2669(3) 1.1965(2) 0.0269(5) Uani 1 1 d .
H7A H 0.9897 0.3120 1.2263 0.032 Uiso 1 1 calc R
C8 C 0.6767(4) 0.1731(3) 1.2686(2) 0.0269(5) Uani 1 1 d .
C9 C 0.4388(4) 0.1122(3) 1.2186(2) 0.0280(5) Uani 1 1 d .
H9A H 0.3348 0.0492 1.2668 0.034 Uiso 1 1 calc R
C10 C 0.7675(5) 0.1383(4) 1.3936(2) 0.0359(6) Uani 1 1 d .
H10A H 0.6355 0.0707 1.4286 0.054 Uiso 1 1 calc R
H10B H 0.8301 0.2560 1.4387 0.054 Uiso 1 1 calc R
H10C H 0.8962 0.0654 1.3949 0.054 Uiso 1 1 calc R
O1 O 0.6528(3) 0.4631(2) 0.64410(15) 0.0298(4) Uani 1 1 d .
O2 O 0.2672(3) 0.4061(2) 0.55681(14) 0.0307(4) Uani 1 1 d .
N1 N 0.5168(3) 0.3272(2) 0.84807(16) 0.0228(4) Uani 1 1 d .
N2 N 0.3831(3) 0.2484(2) 0.92610(16) 0.0219(4) Uani 1 1 d .
N3 N 0.3437(3) 0.1351(3) 1.10782(17) 0.0268(4) Uani 1 1 d .
H1 H 0.675(6) 0.510(5) 0.564(3) 0.072(11) Uiso 1 1 d .
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 0.0207(11) 0.0224(10) 0.0246(11) 0.0031(8) 0.0008(8) 0.0045(8)
C2 0.0222(11) 0.0203(10) 0.0254(11) 0.0031(8) 0.0011(8) 0.0047(8)
C3 0.0206(11) 0.0254(11) 0.0270(12) 0.0029(9) -0.0015(8) 0.0032(8)
C4 0.0186(11) 0.0262(11) 0.0285(12) 0.0036(9) 0.0013(9) 0.0029(8)
C5 0.0217(11) 0.0205(10) 0.0224(11) 0.0015(8) 0.0017(8) 0.0061(8)
C6 0.0223(11) 0.0242(11) 0.0264(11) 0.0003(9) 0.0027(9) 0.0043(8)
C7 0.0229(11) 0.0269(11) 0.0295(12) -0.0010(9) -0.0017(9) 0.0061(9)
C8 0.0325(13) 0.0217(11) 0.0251(12) -0.0013(9) -0.0019(9) 0.0074(9)
C9 0.0304(13) 0.0272(11) 0.0249(12) 0.0036(9) 0.0025(9) 0.0021(9)
C10 0.0390(15) 0.0356(13) 0.0299(14) 0.0016(10) -0.0041(11) 0.0061(11)
O1 0.0213(8) 0.0393(9) 0.0276(9) 0.0083(7) 0.0015(6) 0.0031(7)
O2 0.0248(9) 0.0364(9) 0.0276(9) 0.0099(7) -0.0028(7) 0.0005(7)
N1 0.0213(9) 0.0244(9) 0.0234(9) 0.0045(7) 0.0039(7) 0.0049(7)
N2 0.0182(9) 0.0232(9) 0.0238(9) 0.0034(7) 0.0016(7) 0.0031(7)
N3 0.0251(10) 0.0289(10) 0.0254(10) 0.0047(8) 0.0020(8) 0.0032(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O2 C1 O1 123.7(2)
O2 C1 C2 119.7(2)
O1 C1 C2 116.54(19)
N1 C2 C3 112.3(2)
N1 C2 C1 122.06(19)
C3 C2 C1 125.6(2)
C4 C3 C2 104.70(19)
C3 C4 N2 106.6(2)
N3 C5 C6 124.7(2)
N3 C5 N2 114.43(19)
C6 C5 N2 120.9(2)
C7 C6 C5 117.3(2)
C6 C7 C8 120.3(2)
C9 C8 C7 116.3(2)
C9 C8 C10 121.3(2)
C7 C8 C10 122.4(2)
N3 C9 C8 125.2(2)
C2 N1 N2 103.51(17)
N1 N2 C4 112.86(18)
N1 N2 C5 120.59(17)
C4 N2 C5 126.52(19)
C5 N3 C9 116.22(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.237(3)
C1 O1 1.307(3)
C1 C2 1.462(3)
C2 N1 1.339(3)
C2 C3 1.409(3)
C3 C4 1.364(3)
C4 N2 1.368(3)
C5 N3 1.326(3)
C5 C6 1.389(3)
C5 N2 1.425(3)
C6 C7 1.385(3)
C7 C8 1.396(3)
C8 C9 1.387(3)
C8 C10 1.504(3)
C9 N3 1.340(3)
N1 N2 1.352(3)
