#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/47/2014755.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_2014755
loop_
_publ_author_name
'Zaleski, Jacek'
'Mieczysław Gabryszewski'
'Zarychta, Bartosz'
_publ_section_title
;Tetrakis(1-ethyl-1H-1,2,4-triazole-κN⁴)bis(nitrato-κO)copper(II)
 and
 bis(nitrato-κO)tetrakis(1-propyl-1H-1,2,4-triazole-κN⁴)copper(II)
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m151
_journal_page_last               m154
_journal_paper_doi               10.1107/S0108270105003446
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (N O3)2 (C4 H7 N3)4]'
_chemical_formula_moiety         'C16 H28 Cu N14 O6'
_chemical_formula_sum            'C16 H28 Cu N14 O6'
_chemical_formula_weight         576.06
_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                 99.970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.703(2)
_cell_length_b                   15.288(3)
_cell_length_c                   8.386(2)
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      3.25
_cell_volume                     1225.2(5)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean '1024 x 1024 with blocks 2 x 2'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'ω 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  0.0854
_diffrn_reflns_av_sigmaI/netI    0.1236
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7990
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.955
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             598
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.617
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0448
_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)+(0.023P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                1339
_reflns_number_total             2384
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014755
_cod_database_fobs_code          2014755
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_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 0.01769(19) Uani d S 1 . . Cu
N21 0.6212(4) 0.7040(2) 0.4341(4) 0.0215(8) Uani d . 1 . . N
O1 0.6394(3) 0.62915(16) 0.4990(3) 0.0246(7) Uani d . 1 . . O
O2 0.7199(3) 0.73969(17) 0.3834(4) 0.0382(8) Uani d . 1 . . O
O3 0.5052(3) 0.74097(17) 0.4226(3) 0.0313(7) Uani d . 1 . . O
N4 0.4129(3) 0.5061(2) 0.2633(3) 0.0151(6) Uani d . 1 . . N
C5 0.3603(4) 0.4406(2) 0.1653(4) 0.0177(9) Uani d . 1 . . C
H5A 0.3572 0.3823 0.1963 0.021 Uiso calc R 1 . . H
N1 0.3140(3) 0.47056(19) 0.0193(3) 0.0172(8) Uani d . 1 . . N
N2 0.3337(4) 0.5592(2) 0.0123(4) 0.0248(9) Uani d . 1 . . N
C3 0.3919(4) 0.5766(3) 0.1629(4) 0.0207(9) Uani d . 1 . . C
H3A 0.4168 0.6331 0.1980 0.025 Uiso calc R 1 . . H
C6 0.2467(4) 0.4229(2) -0.1258(4) 0.0238(10) Uani d . 1 . . C
H6A 0.2639 0.3608 -0.1094 0.029 Uiso calc R 1 . . H
H6B 0.2888 0.4410 -0.2174 0.029 Uiso calc R 1 . . H
C7 0.0929(4) 0.4384(3) -0.1641(5) 0.0320(11) Uani d . 1 . . C
H7A 0.0537 0.4055 -0.2585 0.048 Uiso calc R 1 . . H
H7B 0.0753 0.4996 -0.1842 0.048 Uiso calc R 1 . . H
H7C 0.0505 0.4202 -0.0742 0.048 Uiso calc R 1 . . H
N14 0.6643(3) 0.43521(18) 0.4476(3) 0.0158(7) Uani d . 1 . . N
C15 0.6704(4) 0.3636(2) 0.3554(4) 0.0146(8) Uani d . 1 . . C
H15A 0.5934 0.3341 0.2989 0.018 Uiso calc R 1 . . H
N11 0.8016(3) 0.34183(19) 0.3574(3) 0.0179(7) Uani d . 1 . . N
N12 0.8900(3) 0.3977(2) 0.4543(4) 0.0246(8) Uani d . 1 . . N
C13 0.8018(4) 0.4521(2) 0.5038(4) 0.0207(9) Uani d . 1 . . C
H13A 0.8311 0.4989 0.5723 0.025 Uiso calc R 1 . . H
C16 0.8562(4) 0.2685(2) 0.2729(5) 0.0253(10) Uani d . 1 . . C
H16A 0.7865 0.2513 0.1809 0.030 Uiso calc R 1 . . H
H16B 0.8732 0.2189 0.3457 0.030 Uiso calc R 1 . . H
C17 0.9891(5) 0.2922(3) 0.2154(5) 0.0382(12) Uani d . 1 . . C
H17A 1.0226 0.2426 0.1633 0.057 Uiso calc R 1 . . H
H17B 1.0582 0.3095 0.3062 0.057 Uiso calc R 1 . . H
H17C 0.9718 0.3398 0.1399 0.057 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
N14 Cu1 N14 3_666 . 180.00 ?
N14 Cu1 N4 3_666 . 88.79(11) ?
N14 Cu1 N4 . . 91.21(11) y
N14 Cu1 N4 3_666 3_666 91.21(11) ?
N14 Cu1 N4 . 3_666 88.79(11) ?
N4 Cu1 N4 . 3_666 180.00 ?
N14 Cu1 O1 3_666 . 93.74(11) ?
N14 Cu1 O1 . . 86.26(11) y
N4 Cu1 O1 . . 95.68(10) y
N4 Cu1 O1 3_666 . 84.32(10) ?
N14 Cu1 O1 3_666 3_666 86.26(11) ?
N14 Cu1 O1 . 3_666 93.74(11) ?
N4 Cu1 O1 . 3_666 84.32(10) ?
N4 Cu1 O1 3_666 3_666 95.68(10) ?
O1 Cu1 O1 . 3_666 180.00 ?
O2 N21 O3 . . 120.9(3) y
O2 N21 O1 . . 119.1(3) y
O3 N21 O1 . . 120.0(3) y
N21 O1 Cu1 . . 135.2(2) y
C5 N4 C3 . . 102.3(3) ?
C5 N4 Cu1 . . 128.2(3) ?
C3 N4 Cu1 . . 129.5(2) ?
N1 C5 N4 . . 110.2(3) ?
N1 C5 H5A . . 124.9 ?
N4 C5 H5A . . 124.9 ?
C5 N1 N2 . . 110.9(3) ?
C5 N1 C6 . . 129.1(3) ?
N2 N1 C6 . . 120.0(3) ?
C3 N2 N1 . . 101.5(3) ?
N2 C3 N4 . . 115.2(3) ?
N2 C3 H3A . . 122.4 ?
N4 C3 H3A . . 122.4 ?
N1 C6 C7 . . 112.6(3) ?
N1 C6 H6A . . 109.1 ?
C7 C6 H6A . . 109.1 ?
N1 C6 H6B . . 109.1 ?
C7 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.8 ?
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 ?
C15 N14 C13 . . 102.4(3) ?
C15 N14 Cu1 . . 130.4(3) ?
C13 N14 Cu1 . . 127.2(2) ?
N11 C15 N14 . . 109.7(3) ?
N11 C15 H15A . . 125.1 ?
N14 C15 H15A . . 125.1 ?
C15 N11 N12 . . 110.8(3) ?
C15 N11 C16 . . 128.0(3) ?
N12 N11 C16 . . 121.2(3) ?
C13 N12 N11 . . 102.0(3) ?
N12 C13 N14 . . 115.1(3) ?
N12 C13 H13A . . 122.5 ?
N14 C13 H13A . . 122.5 ?
N11 C16 C17 . . 111.9(3) ?
N11 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
N11 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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 N14 3_666 1.990(3) ?
Cu1 N14 . 1.990(3) y
Cu1 N4 . 2.020(3) y
Cu1 N4 3_666 2.020(3) ?
Cu1 O1 . 2.394(3) y
Cu1 O1 3_666 2.394(3) ?
N21 O2 . 1.239(4) y
N21 O3 . 1.248(4) y
N21 O1 . 1.266(4) y
N4 C5 . 1.339(4) ?
N4 C3 . 1.362(4) ?
C5 N1 . 1.312(4) ?
C5 H5A . 0.9300 ?
N1 N2 . 1.371(4) ?
N1 C6 . 1.470(4) ?
N2 C3 . 1.318(4) ?
C3 H3A . 0.9300 ?
C6 C7 . 1.491(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
N14 C15 . 1.347(4) ?
N14 C13 . 1.361(4) ?
C15 N11 . 1.312(4) ?
C15 H15A . 0.9300 ?
N11 N12 . 1.373(4) ?
N11 C16 . 1.473(4) ?
N12 C13 . 1.311(4) ?
C13 H13A . 0.9300 ?
C16 C17 . 1.498(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3A O3 . 0.93 2.54 3.382(5) 151
C5 H5A O2 2_645 0.93 2.36 3.178(5) 146
C5 H5A O1 3_666 0.93 2.56 3.010(4) 111
C15 H15A O3 2_645 0.93 2.40 3.237(4) 149
C17 H17A O2 2_745 0.96 2.60 3.180(5) 120
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_site_symmetry_1
_geom_torsion
O2 N21 O1 Cu1 . -142.7(3)
O3 N21 O1 Cu1 . 37.6(5)
N14 Cu1 O1 N21 3_666 -49.2(3)
N14 Cu1 O1 N21 . 130.8(3)
N4 Cu1 O1 N21 . 39.9(3)
N4 Cu1 O1 N21 3_666 -140.1(3)
N14 Cu1 N4 C5 3_666 -111.4(3)
N14 Cu1 N4 C5 . 68.6(3)
O1 Cu1 N4 C5 . 155.0(3)
O1 Cu1 N4 C5 3_666 -25.0(3)
N14 Cu1 N4 C3 3_666 68.4(3)
O1 Cu1 N4 C3 . -25.2(3)
O1 Cu1 N4 C3 3_666 154.8(3)
C3 N4 C5 N1 . 0.7(4)
Cu1 N4 C5 N1 . -179.5(2)
N4 C5 N1 N2 . 0.1(4)
N4 C5 N1 C6 . -179.2(3)
C5 N1 N2 C3 . -0.8(4)
C6 N1 N2 C3 . 178.5(3)
N1 N2 C3 N4 . 1.2(5)
C5 N4 C3 N2 . -1.2(4)
Cu1 N4 C3 N2 . 179.0(3)
C5 N1 C6 C7 . 104.8(4)
N2 N1 C6 C7 . -74.3(4)
N4 Cu1 N14 C15 . -50.2(3)
N4 Cu1 N14 C15 3_666 129.8(3)
O1 Cu1 N14 C15 . -145.8(3)
O1 Cu1 N14 C15 3_666 34.2(3)
N4 Cu1 N14 C13 . 132.4(3)
N4 Cu1 N14 C13 3_666 -47.6(3)
O1 Cu1 N14 C13 . 36.8(3)
O1 Cu1 N14 C13 3_666 -143.2(3)
C13 N14 C15 N11 . -0.6(4)
Cu1 N14 C15 N11 . -178.5(2)
N14 C15 N11 N12 . 1.0(4)
N14 C15 N11 C16 . -179.6(3)
C15 N11 N12 C13 . -0.9(4)
C16 N11 N12 C13 . 179.6(3)
N11 N12 C13 N14 . 0.5(4)
C15 N14 C13 N12 . 0.0(4)
Cu1 N14 C13 N12 . 178.0(2)
C15 N11 C16 C17 . 144.1(4)
N12 N11 C16 C17 . -36.6(5)
