#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/77/4307730.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_4307730
loop_
_publ_author_name
'Guillermo A. Santillan'
'Carl J. Carrano'
_publ_section_title
;
Synthesis and Characterization of Copper(II) Complexes of Nonfacially
Coordinating Heteroscorpionate Ligands
(4-Carboxyphenyl)bis(3,5-dimethylpyrazolyl)methane and
(3-Carboxyphenyl)bis(3,5-dimethylpyrazolyl)methane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1751
_journal_page_last               1759
_journal_paper_doi               10.1021/ic062226u
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C18 H19 N4 O2'
_chemical_formula_weight         323.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.574(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7148(8)
_cell_length_b                   9.6352(7)
_cell_length_c                   13.8772(10)
_cell_measurement_reflns_used    4711
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.57
_cell_volume                     1700.0(2)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20576
_diffrn_reflns_theta_full        22.41
_diffrn_reflns_theta_max         22.41
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   SADABS-multiscan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1327P)²+0.5599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1827
_reflns_number_gt                1712
_reflns_number_total             2193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062226usi20061122_013921.cif
_cod_data_source_block           justin104a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_database_code               4307730
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.24957(18) -0.2774(2) 0.35136(17) 0.0380(7) Uani 1 1 d . . .
N2 N 0.28452(18) -0.1792(2) 0.41484(16) 0.0346(6) Uani 1 1 d . . .
N3 N 0.15046(17) 0.1052(2) 0.45833(15) 0.0337(6) Uani 1 1 d . . .
N4 N 0.18001(17) 0.0242(2) 0.38211(15) 0.0300(6) Uani 1 1 d . . .
O1 O 0.25357(16) 0.2878(2) 0.10395(14) 0.0501(7) Uani 1 1 d . . .
O2 O 0.39927(17) 0.2757(2) 0.01665(16) 0.0558(7) Uani 1 1 d . . .
C1 C 0.3426(3) -0.1484(4) 0.5868(2) 0.0648(11) Uani 1 1 d . . .
H1B H 0.3504 -0.0535 0.5670 0.097 Uiso 1 1 calc R . .
H1C H 0.4096 -0.1841 0.6076 0.097 Uiso 1 1 calc R . .
H1D H 0.2938 -0.1534 0.6390 0.097 Uiso 1 1 calc R . .
C2 C 0.3026(2) -0.2319(3) 0.5047(2) 0.0399(8) Uani 1 1 d . . .
C3 C 0.2781(2) -0.3697(3) 0.4972(2) 0.0468(9) Uani 1 1 d . . .
H3B H 0.2820 -0.4352 0.5463 0.056 Uiso 1 1 calc R . .
C4 C 0.2464(2) -0.3935(3) 0.4021(2) 0.0405(8) Uani 1 1 d . . .
C5 C 0.2108(3) -0.5267(3) 0.3568(3) 0.0598(10) Uani 1 1 d . . .
H5A H 0.1943 -0.5111 0.2900 0.090 Uiso 1 1 calc R . .
H5B H 0.1494 -0.5600 0.3892 0.090 Uiso 1 1 calc R . .
H5C H 0.2659 -0.5945 0.3621 0.090 Uiso 1 1 calc R . .
C6 C -0.0042(3) 0.2382(4) 0.5082(2) 0.0517(9) Uani 1 1 d . . .
H6A H 0.0410 0.2586 0.5622 0.078 Uiso 1 1 calc R . .
H6B H -0.0667 0.1929 0.5303 0.078 Uiso 1 1 calc R . .
H6C H -0.0230 0.3230 0.4761 0.078 Uiso 1 1 calc R . .
C7 C 0.0524(2) 0.1446(3) 0.4393(2) 0.0365(8) Uani 1 1 d . . .
C8 C 0.0185(2) 0.0879(3) 0.3523(2) 0.0393(8) Uani 1 1 d . . .
H8A H -0.0475 0.0993 0.3239 0.047 Uiso 1 1 calc R . .
C9 C 0.1000(2) 0.0121(3) 0.3161(2) 0.0343(8) Uani 1 1 d . . .
C10 C 0.1051(2) -0.0682(3) 0.2246(2) 0.0468(9) Uani 1 1 d . . .
H10A H 0.0394 -0.0602 0.1905 0.070 Uiso 1 1 calc R . .
H10B H 0.1188 -0.1640 0.2388 0.070 Uiso 1 1 calc R . .
H10C H 0.1606 -0.0321 0.1854 0.070 Uiso 1 1 calc R . .
C11 C 0.2864(2) -0.0338(3) 0.38656(19) 0.0305(7) Uani 1 1 d . . .
H11A H 0.3229 0.0155 0.4389 0.037 Uiso 1 1 calc R . .
C12 C 0.3495(2) -0.0064(3) 0.29667(19) 0.0288(7) Uani 1 1 d . . .
C13 C 0.4380(2) -0.0848(3) 0.2762(2) 0.0382(8) Uani 1 1 d . . .
H13A H 0.4557 -0.1593 0.3157 0.046 Uiso 1 1 calc R . .
C14 C 0.4998(2) -0.0541(3) 0.1987(2) 0.0436(8) Uani 1 1 d . . .
H14A H 0.5596 -0.1067 0.1869 0.052 Uiso 1 1 calc R . .
C15 C 0.4738(2) 0.0549(3) 0.1376(2) 0.0397(8) Uani 1 1 d . . .
H15A H 0.5153 0.0751 0.0847 0.048 Uiso 1 1 calc R . .
C16 C 0.3848(2) 0.1333(3) 0.15676(19) 0.0317(7) Uani 1 1 d . . .
C17 C 0.3245(2) 0.1031(3) 0.23655(19) 0.0305(7) Uani 1 1 d . . .
H17A H 0.2661 0.1576 0.2499 0.037 Uiso 1 1 calc R . .
C18 C 0.3487(2) 0.2400(3) 0.0858(2) 0.0374(8) Uani 1 1 d . . .
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'
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
C4 N1 N2 104.7(2) . . ?
N1 N2 C2 112.5(2) . . ?
N1 N2 C11 120.0(2) . . ?
C2 N2 C11 127.0(2) . . ?
C7 N3 N4 105.9(2) . . ?
C9 N4 N3 111.0(2) . . ?
C9 N4 C11 132.6(2) . . ?
N3 N4 C11 116.4(2) . . ?
N2 C2 C3 104.8(3) . . ?
N2 C2 C1 123.7(3) . . ?
C3 C2 C1 131.4(3) . . ?
C2 C3 C4 107.2(3) . . ?
N1 C4 C3 110.7(3) . . ?
N1 C4 C5 120.8(3) . . ?
C3 C4 C5 128.5(3) . . ?
N3 C7 C8 110.0(2) . . ?
N3 C7 C6 120.0(3) . . ?
C8 C7 C6 130.0(3) . . ?
C9 C8 C7 107.4(2) . . ?
C8 C9 N4 105.6(2) . . ?
C8 C9 C10 129.1(3) . . ?
N4 C9 C10 125.3(3) . . ?
N2 C11 N4 111.2(2) . . ?
N2 C11 C12 113.6(2) . . ?
N4 C11 C12 113.3(2) . . ?
C17 C12 C13 118.4(2) . . ?
C17 C12 C11 120.7(2) . . ?
C13 C12 C11 120.8(2) . . ?
C14 C13 C12 121.0(3) . . ?
C13 C14 C15 120.5(3) . . ?
C16 C15 C14 119.0(3) . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 C18 119.6(3) . . ?
C17 C16 C18 120.3(2) . . ?
C12 C17 C16 121.2(3) . . ?
O2 C18 O1 123.2(3) . . ?
O2 C18 C16 123.8(3) . . ?
O1 C18 C16 113.0(2) . . ?
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
N1 C4 1.322(4) . ?
N1 N2 1.364(3) . ?
N2 C2 1.363(4) . ?
N2 C11 1.455(4) . ?
N3 C7 1.328(3) . ?
N3 N4 1.370(3) . ?
N4 C9 1.367(4) . ?
N4 C11 1.465(3) . ?
O1 C18 1.321(4) . ?
O2 C18 1.210(3) . ?
C1 C2 1.481(5) . ?
C2 C3 1.367(4) . ?
C3 C4 1.396(5) . ?
C4 C5 1.497(5) . ?
C6 C7 1.503(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.368(4) . ?
C9 C10 1.489(4) . ?
C11 C12 1.513(4) . ?
C12 C17 1.380(4) . ?
C12 C13 1.386(4) . ?
C13 C14 1.371(4) . ?
C14 C15 1.387(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.384(4) . ?
C16 C18 1.493(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660845
