#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/48/2014868.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014868
loop_
_publ_author_name
'Fredy R. Pérez'
'Julio Belmar'
'Claudio Jiménez'
'Yanko Moreno'
'Patricio Hermosilla'
'Ricardo Baggio'
_publ_section_title
;Bis{1-n-hexyl-3-methyl-4-[1-(phenylimino)propyl]-1H-pyrazol-5-olato}copper(II):
 a new copper(II) complex with a chelating alkylpyrazolone-based enamine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m318
_journal_page_last               m320
_journal_paper_doi               10.1107/S0108270105014538
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (C19 H26 N3 O)2]'
_chemical_formula_moiety         'C38 H52 Cu N6 O2'
_chemical_formula_sum            'C38 H52 Cu N6 O2'
_chemical_formula_weight         688.40
_chemical_melting_point          396(2)
_chemical_name_systematic
Bis{1-(n-hexyl)-3-methyl-4-[1-(phenylimino)propyl]-2-pyrazol-5-olato}copper(II)
_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           SHELXL97
_cell_angle_alpha                94.121(2)
_cell_angle_beta                 95.416(2)
_cell_angle_gamma                115.946(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0366(10)
_cell_length_b                   8.8767(11)
_cell_length_c                   14.3438(17)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.45
_cell_measurement_theta_min      3.62
_cell_volume                     908.67(19)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7009
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             367
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1386
_reflns_number_gt                2449
_reflns_number_total             3530
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob1229.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2014868
_cod_database_fobs_code          2014868
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.5000 0.5000 0.5000 0.0370(2) Uani d S 1 . . Cu
O1 0.5640(4) 0.4339(3) 0.38683(16) 0.0498(7) Uani d . 1 . . O
N1 0.7606(4) 0.3657(4) 0.3059(2) 0.0458(8) Uani d . 1 . . N
N2 0.8911(4) 0.3055(4) 0.3202(2) 0.0477(8) Uani d . 1 . . N
N3 0.6102(4) 0.3711(3) 0.57545(19) 0.0365(7) Uani d . 1 . . N
C1 0.6876(5) 0.3793(4) 0.3852(3) 0.0388(9) Uani d . 1 . . C
C2 0.7755(5) 0.3259(4) 0.4561(2) 0.0342(8) Uani d . 1 . . C
C3 0.9011(5) 0.2823(4) 0.4096(3) 0.0410(9) Uani d . 1 . . C
C4 1.0364(5) 0.2195(5) 0.4442(3) 0.0563(11) Uani d . 1 . . C
H4A 1.1069 0.2137 0.3948 0.084 Uiso calc R 1 . . H
H4B 0.9699 0.1091 0.4626 0.084 Uiso calc R 1 . . H
H4C 1.1198 0.2952 0.4976 0.084 Uiso calc R 1 . . H
C5 0.7292(5) 0.3166(4) 0.5493(3) 0.0372(9) Uani d . 1 . . C
C6 0.8135(5) 0.2364(5) 0.6155(3) 0.0498(10) Uani d . 1 . . C
H6A 0.8165 0.2791 0.6801 0.060 Uiso calc R 1 . . H
H6B 0.9412 0.2675 0.6048 0.060 Uiso calc R 1 . . H
C7 0.7035(6) 0.0449(5) 0.6019(3) 0.0643(13) Uani d . 1 . . C
H7A 0.7672 -0.0022 0.6412 0.096 Uiso calc R 1 . . H
H7B 0.6929 0.0028 0.5370 0.096 Uiso calc R 1 . . H
H7C 0.5810 0.0133 0.6189 0.096 Uiso calc R 1 . . H
C8 0.5561(5) 0.3405(5) 0.6682(3) 0.0428(9) Uani d . 1 . . C
C9 0.3911(6) 0.2032(5) 0.6772(3) 0.0590(12) Uani d . 1 . . C
H9A 0.3144 0.1333 0.6235 0.071 Uiso calc R 1 . . H
C10 0.3390(7) 0.1688(6) 0.7648(4) 0.0719(14) Uani d . 1 . . C
H10A 0.2287 0.0744 0.7699 0.086 Uiso calc R 1 . . H
C11 0.4473(8) 0.2715(7) 0.8440(4) 0.0762(15) Uani d . 1 . . C
H11A 0.4116 0.2474 0.9031 0.091 Uiso calc R 1 . . H
C12 0.6092(7) 0.4108(7) 0.8359(3) 0.0692(14) Uani d . 1 . . C
H12A 0.6830 0.4818 0.8899 0.083 Uiso calc R 1 . . H
C13 0.6642(6) 0.4470(5) 0.7484(3) 0.0556(11) Uani d . 1 . . C
H13A 0.7735 0.5426 0.7436 0.067 Uiso calc R 1 . . H
C14 0.7233(6) 0.4135(5) 0.2151(3) 0.0560(11) Uani d . 1 . . C
H14A 0.8412 0.4844 0.1943 0.067 Uiso calc R 1 . . H
H14B 0.6553 0.4800 0.2219 0.067 Uiso calc R 1 . . H
C15 0.6118(7) 0.2645(6) 0.1400(3) 0.0678(13) Uani d . 1 . . C
H15A 0.5973 0.3061 0.0806 0.081 Uiso calc R 1 . . H
H15B 0.6813 0.1997 0.1319 0.081 Uiso calc R 1 . . H
C16 0.4214(7) 0.1497(6) 0.1628(3) 0.0738(14) Uani d . 1 . . C
H16A 0.3544 0.2160 0.1740 0.089 Uiso calc R 1 . . H
H16B 0.4364 0.1042 0.2207 0.089 Uiso calc R 1 . . H
C17 0.3049(7) 0.0050(6) 0.0865(3) 0.0758(14) Uani d . 1 . . C
H17A 0.2868 0.0509 0.0292 0.091 Uiso calc R 1 . . H
H17B 0.3742 -0.0586 0.0737 0.091 Uiso calc R 1 . . H
C18 0.1176(8) -0.1137(7) 0.1092(4) 0.0977(18) Uani d . 1 . . C
H18A 0.0481 -0.0503 0.1218 0.117 Uiso calc R 1 . . H
H18B 0.1356 -0.1597 0.1665 0.117 Uiso calc R 1 . . H
C19 0.0025(8) -0.2575(7) 0.0330(4) 0.111(2) Uani d . 1 . . C
H19A -0.1172 -0.3245 0.0517 0.166 Uiso calc R 1 . . H
H19B 0.0656 -0.3264 0.0232 0.166 Uiso calc R 1 . . H
H19C -0.0144 -0.2137 -0.0245 0.166 Uiso calc R 1 . . H
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'
Cu Cu 0.3201 1.2651 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 . 2_666 180.00(7) no
O1 Cu1 N3 . . 92.24(11) y
O1 Cu1 N3 2_666 . 87.76(11) ?
O1 Cu1 N3 . 2_666 87.76(11) ?
O1 Cu1 N3 2_666 2_666 92.24(11) ?
N3 Cu1 N3 . 2_666 180.00(13) no
C1 O1 Cu1 . . 122.5(2) ?
C1 N1 N2 . . 112.1(3) ?
C1 N1 C14 . . 127.7(3) ?
N2 N1 C14 . . 120.1(3) ?
C3 N2 N1 . . 105.9(3) ?
C5 N3 C8 . . 116.8(3) ?
C5 N3 Cu1 . . 126.6(2) ?
C8 N3 Cu1 . . 116.6(2) ?
O1 C1 N1 . . 121.9(3) ?
O1 C1 C2 . . 131.7(3) ?
N1 C1 C2 . . 106.4(3) ?
C1 C2 C5 . . 122.8(3) ?
C1 C2 C3 . . 104.4(3) ?
C5 C2 C3 . . 132.8(3) ?
N2 C3 C2 . . 111.2(3) ?
N2 C3 C4 . . 116.8(3) ?
C2 C3 C4 . . 132.0(4) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N3 C5 C2 . . 120.6(3) ?
N3 C5 C6 . . 121.3(3) ?
C2 C5 C6 . . 118.1(3) ?
C5 C6 C7 . . 111.9(3) ?
C5 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
C5 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C13 . . 118.8(4) ?
C9 C8 N3 . . 119.5(3) ?
C13 C8 N3 . . 121.7(3) ?
C10 C9 C8 . . 120.6(4) ?
C10 C9 H9A . . 119.7 ?
C8 C9 H9A . . 119.7 ?
C11 C10 C9 . . 120.6(5) ?
C11 C10 H10A . . 119.7 ?
C9 C10 H10A . . 119.7 ?
C10 C11 C12 . . 119.4(4) ?
C10 C11 H11A . . 120.3 ?
C12 C11 H11A . . 120.3 ?
C11 C12 C13 . . 120.7(4) ?
C11 C12 H12A . . 119.6 ?
C13 C12 H12A . . 119.6 ?
C8 C13 C12 . . 119.7(4) ?
C8 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
N1 C14 C15 . . 113.5(3) ?
N1 C14 H14A . . 108.9 ?
C15 C14 H14A . . 108.9 ?
N1 C14 H14B . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C16 C15 C14 . . 113.5(4) ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15B . . 108.9 ?
C14 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
C15 C16 C17 . . 114.1(4) ?
C15 C16 H16A . . 108.7 ?
C17 C16 H16A . . 108.7 ?
C15 C16 H16B . . 108.7 ?
C17 C16 H16B . . 108.7 ?
H16A C16 H16B . . 107.6 ?
C18 C17 C16 . . 114.9(4) ?
C18 C17 H17A . . 108.6 ?
C16 C17 H17A . . 108.6 ?
C18 C17 H17B . . 108.6 ?
C16 C17 H17B . . 108.6 ?
H17A C17 H17B . . 107.5 ?
C17 C18 C19 . . 114.6(5) ?
C17 C18 H18A . . 108.6 ?
C19 C18 H18A . . 108.6 ?
C17 C18 H18B . . 108.6 ?
C19 C18 H18B . . 108.6 ?
H18A C18 H18B . . 107.6 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.879(2) y
Cu1 O1 2_666 1.879(2) ?
Cu1 N3 . 2.036(3) y
Cu1 N3 2_666 2.036(3) ?
O1 C1 . 1.282(4) y
N1 C1 . 1.349(4) y
N1 N2 . 1.375(4) y
N1 C14 . 1.445(5) y
N2 C3 . 1.314(4) y
N3 C5 . 1.317(4) y
N3 C8 . 1.446(4) y
C1 C2 . 1.409(5) y
C2 C5 . 1.420(5) y
C2 C3 . 1.430(5) y
C3 C4 . 1.486(5) y
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.506(5) ?
C6 C7 . 1.521(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.378(5) ?
C8 C13 . 1.381(5) ?
C9 C10 . 1.374(5) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.360(6) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.370(6) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.383(5) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 C15 . 1.513(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.505(6) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.509(6) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.495(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.502(6) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
