#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:20:00 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179719 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/21/7002148.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_7002148
loop_
_publ_author_name
'Sarma, Rupam'
'Kalita, Dipjyoti'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Solvent induced reactivity of 3,5-dimethylpyrazole towards zinc (II)
 carboxylates
;
_journal_issue                   36
_journal_name_full               'Dalton Transactions'
_journal_page_first              7428
_journal_page_last               7436
_journal_paper_doi               10.1039/b905534g
_journal_year                    2009
_chemical_formula_sum            'C24 H26 N4 O4 Zn'
_chemical_formula_weight         499.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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
_cell_angle_alpha                96.598(2)
_cell_angle_beta                 103.186(2)
_cell_angle_gamma                108.004(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7460(3)
_cell_length_b                   12.0489(4)
_cell_length_c                   13.0519(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1247.78(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6812
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    1.020
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.5034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                3507
_reflns_number_total             4202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b905534g.txt
_cod_data_source_block           znbendmp_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7002148
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.38474(3) 0.14622(2) 0.29602(2) 0.05714(12) Uani 1 1 d . . .
O1 O 0.4271(2) 0.01609(15) 0.21973(15) 0.0719(5) Uani 1 1 d . . .
O2 O 0.3319(3) -0.13152(16) 0.30282(17) 0.0829(6) Uani 1 1 d . . .
O3 O 0.5869(2) 0.27949(15) 0.31329(15) 0.0730(5) Uani 1 1 d . . .
O4 O 0.4926(2) 0.41990(17) 0.25640(18) 0.0835(6) Uani 1 1 d . . .
N1 N 0.3431(3) 0.12259(18) 0.43798(16) 0.0610(5) Uani 1 1 d . . .
N2 N 0.2897(2) 0.01211(18) 0.46083(17) 0.0615(5) Uani 1 1 d . . .
H2 H 0.2900 -0.0509 0.4227 0.074 Uiso 1 1 d R . .
N3 N 0.1782(3) 0.16114(18) 0.20188(16) 0.0614(5) Uani 1 1 d . . .
N4 N 0.1764(3) 0.2654(2) 0.17287(17) 0.0667(5) Uani 1 1 d . . .
H4A H 0.2617 0.3302 0.1921 0.080 Uiso 1 1 d R . .
C1 C 0.3946(3) -0.0912(2) 0.2329(2) 0.0596(6) Uani 1 1 d . . .
C2 C 0.4356(3) -0.1718(2) 0.15534(19) 0.0557(6) Uani 1 1 d . . .
C3 C 0.4958(3) -0.1311(2) 0.0731(2) 0.0692(7) Uani 1 1 d . . .
H3 H 0.5144 -0.0522 0.0667 0.083 Uiso 1 1 calc R . .
C4 C 0.5290(4) -0.2065(3) -0.0002(3) 0.0906(9) Uani 1 1 d . . .
H4 H 0.5683 -0.1785 -0.0561 0.109 Uiso 1 1 calc R . .
C5 C 0.5040(5) -0.3216(3) 0.0095(3) 0.0948(10) Uani 1 1 d . . .
H5 H 0.5260 -0.3723 -0.0399 0.114 Uiso 1 1 calc R . .
C6 C 0.4464(4) -0.3630(3) 0.0925(3) 0.0908(10) Uani 1 1 d . . .
H6 H 0.4311 -0.4413 0.0996 0.109 Uiso 1 1 calc R . .
C7 C 0.4113(4) -0.2893(2) 0.1645(2) 0.0761(8) Uani 1 1 d . . .
H7 H 0.3711 -0.3181 0.2199 0.091 Uiso 1 1 calc R . .
C8 C 0.6069(3) 0.3823(2) 0.2900(2) 0.0608(6) Uani 1 1 d . . .
C9 C 0.7846(3) 0.4612(2) 0.3072(2) 0.0607(6) Uani 1 1 d . . .
C10 C 0.8190(4) 0.5718(2) 0.2789(3) 0.0788(8) Uani 1 1 d . . .
H10 H 0.7312 0.5957 0.2471 0.095 Uiso 1 1 calc R . .
C11 C 0.9823(4) 0.6470(3) 0.2975(3) 0.0926(10) Uani 1 1 d . . .
H11 H 1.0035 0.7204 0.2770 0.111 Uiso 1 1 calc R . .
C12 C 1.1119(4) 0.6141(3) 0.3455(3) 0.0977(10) Uani 1 1 d . . .
H12 H 1.2216 0.6659 0.3601 0.117 Uiso 1 1 calc R . .
C13 C 1.0808(4) 0.5050(4) 0.3723(4) 0.1243(15) Uani 1 1 d . . .
H13 H 1.1694 0.4816 0.4037 0.149 Uiso 1 1 calc R . .
C14 C 0.9170(4) 0.4285(3) 0.3528(3) 0.0997(11) Uani 1 1 d . . .
H14 H 0.8971 0.3539 0.3709 0.120 Uiso 1 1 calc R . .
C15 C 0.3698(5) 0.3262(3) 0.5162(3) 0.0996(11) Uani 1 1 d . . .
H15A H 0.4327 0.3463 0.4654 0.149 Uiso 1 1 calc R . .
H15B H 0.4364 0.3703 0.5867 0.149 Uiso 1 1 calc R . .
H15C H 0.2699 0.3457 0.4969 0.149 Uiso 1 1 calc R . .
C16 C 0.3234(3) 0.1957(2) 0.5154(2) 0.0669(7) Uani 1 1 d . . .
C17 C 0.2566(4) 0.1296(3) 0.5853(2) 0.0746(7) Uani 1 1 d . . .
H17 H 0.2302 0.1588 0.6455 0.089 Uiso 1 1 calc R . .
C18 C 0.2369(3) 0.0130(2) 0.5490(2) 0.0628(6) Uani 1 1 d . . .
C19 C 0.1736(4) -0.0979(3) 0.5905(3) 0.0838(8) Uani 1 1 d . . .
H19A H 0.0590 -0.1166 0.5749 0.101 Uiso 1 1 d R . .
H19B H 0.2116 -0.1502 0.5568 0.101 Uiso 1 1 d R . .
H19C H 0.2274 -0.0738 0.6669 0.101 Uiso 1 1 d R . .
C20 C -0.0055(5) 0.3594(4) 0.0693(4) 0.1261(15) Uani 1 1 d . . .
H20A H -0.1190 0.3498 0.0690 0.151 Uiso 1 1 d R . .
H20B H 0.0713 0.4277 0.1142 0.151 Uiso 1 1 d R . .
H20C H 0.0029 0.3504 -0.0025 0.151 Uiso 1 1 d R . .
C21 C 0.0271(4) 0.2552(3) 0.1114(3) 0.0855(9) Uani 1 1 d . . .
C22 C -0.0725(4) 0.1390(3) 0.0992(3) 0.1058(12) Uani 1 1 d . . .
H22 H -0.1845 0.1043 0.0600 0.127 Uiso 1 1 calc R . .
C23 C 0.0246(4) 0.0830(3) 0.1562(2) 0.0764(8) Uani 1 1 d . . .
C24 C -0.0207(4) -0.0439(3) 0.1715(3) 0.1066(12) Uani 1 1 d . . .
H24A H -0.0080 -0.0925 0.1126 0.160 Uiso 1 1 calc R . .
H24B H -0.1348 -0.0727 0.1742 0.160 Uiso 1 1 calc R . .
H24C H 0.0517 -0.0475 0.2375 0.160 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 0.0000 0.0000 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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
O3 Zn1 O1 102.45(8) . . ?
O3 Zn1 N1 111.36(8) . . ?
O1 Zn1 N1 114.59(8) . . ?
O3 Zn1 N3 113.87(8) . . ?
O1 Zn1 N3 106.87(8) . . ?
N1 Zn1 N3 107.72(8) . . ?
C1 O1 Zn1 129.26(17) . . ?
C8 O3 Zn1 130.49(18) . . ?
C16 N1 N2 105.6(2) . . ?
C16 N1 Zn1 131.26(17) . . ?
N2 N1 Zn1 121.57(16) . . ?
C18 N2 N1 112.2(2) . . ?
C18 N2 H2 124.1 . . ?
N1 N2 H2 123.8 . . ?
C23 N3 N4 105.8(2) . . ?
C23 N3 Zn1 132.17(19) . . ?
N4 N3 Zn1 122.02(16) . . ?
C21 N4 N3 111.9(2) . . ?
C21 N4 H4A 124.2 . . ?
N3 N4 H4A 123.9 . . ?
O2 C1 O1 124.9(2) . . ?
O2 C1 C2 119.5(2) . . ?
O1 C1 C2 115.6(2) . . ?
C3 C2 C7 118.8(2) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 120.6(2) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
O4 C8 O3 125.0(2) . . ?
O4 C8 C9 119.2(2) . . ?
O3 C8 C9 115.8(2) . . ?
C14 C9 C10 117.9(3) . . ?
C14 C9 C8 121.9(2) . . ?
C10 C9 C8 120.2(2) . . ?
C9 C10 C11 120.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 121.0(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 109.0(2) . . ?
N1 C16 C15 120.7(3) . . ?
C17 C16 C15 130.3(3) . . ?
C18 C17 C16 107.3(3) . . ?
C18 C17 H17 126.3 . . ?
C16 C17 H17 126.3 . . ?
N2 C18 C17 105.8(2) . . ?
N2 C18 C19 121.9(3) . . ?
C17 C18 C19 132.3(3) . . ?
C18 C19 H19A 105.7 . . ?
C18 C19 H19B 103.7 . . ?
H19A C19 H19B 117.1 . . ?
C18 C19 H19C 103.6 . . ?
H19A C19 H19C 112.1 . . ?
H19B C19 H19C 113.0 . . ?
C21 C20 H20A 105.4 . . ?
C21 C20 H20B 107.8 . . ?
H20A C20 H20B 113.1 . . ?
C21 C20 H20C 106.1 . . ?
H20A C20 H20C 109.9 . . ?
H20B C20 H20C 114.0 . . ?
N4 C21 C22 106.0(3) . . ?
N4 C21 C20 121.6(3) . . ?
C22 C21 C20 132.5(3) . . ?
C21 C22 C23 107.1(3) . . ?
C21 C22 H22 126.4 . . ?
C23 C22 H22 126.4 . . ?
N3 C23 C22 109.2(3) . . ?
N3 C23 C24 120.8(3) . . ?
C22 C23 C24 129.9(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
Zn1 O3 1.9325(17) . ?
Zn1 O1 1.9380(17) . ?
Zn1 N1 2.003(2) . ?
Zn1 N3 2.011(2) . ?
O1 C1 1.276(3) . ?
O2 C1 1.239(3) . ?
O3 C8 1.279(3) . ?
O4 C8 1.234(3) . ?
N1 C16 1.340(3) . ?
N1 N2 1.360(3) . ?
N2 C18 1.335(3) . ?
N2 H2 0.8600 . ?
N3 C23 1.330(3) . ?
N3 N4 1.357(3) . ?
N4 C21 1.328(3) . ?
N4 H4A 0.8594 . ?
C1 C2 1.500(3) . ?
C2 C3 1.374(4) . ?
C2 C7 1.389(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.499(4) . ?
C9 C14 1.368(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.496(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.390(4) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.494(4) . ?
C19 H19A 0.9239 . ?
C19 H19B 0.9136 . ?
C19 H19C 0.9661 . ?
C20 C21 1.505(5) . ?
C20 H20A 0.9624 . ?
C20 H20B 0.9167 . ?
C20 H20C 0.9527 . ?
C21 C22 1.370(5) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.506(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O4 0.86 1.90 2.698(3) 153.3 .
N2 H2 O2 0.86 1.91 2.703(3) 152.1 .
