#------------------------------------------------------------------------------
#$Date: 2018-01-16 07:23:00 +0200 (Tue, 16 Jan 2018) $
#$Revision: 205243 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229988.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_7229988
loop_
_publ_author_name
'Li, Jie'
'Liu, Huiyu'
'Guo, Zhaoqi'
'Yang, Mingyan'
'Song, Jirong'
'Ma, Haixia'
_publ_section_title
;
 Two Cu(ii)-triadimenol complexes as potential fungicides: synergistic
 actions and DFT calculations
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              2933
_journal_paper_doi               10.1039/C7RA10572J
_journal_volume                  8
_journal_year                    2018
_chemical_formula_sum            'C32 H42 Cl2 Cu N6 O8'
_chemical_formula_weight         773.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2014/7
_audit_update_record
;
2015-11-07 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                111.668(4)
_cell_angle_beta                 108.999(4)
_cell_angle_gamma                96.088(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5849(16)
_cell_length_b                   10.5243(19)
_cell_length_c                   12.043(3)
_cell_measurement_reflns_used    2530
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.21
_cell_volume                     923.9(3)
_computing_cell_refinement       ' SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.155
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             403
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0741P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3022
_reflns_number_total             3399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ra10572j2.cif
_cod_data_source_block           2
_cod_database_code               7229988
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.831
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 1.5000 0.5000 1.0000 0.03320(16) Uani 1 2 d S . P
Cl1 Cl 1.31475(11) -0.50958(8) 0.54805(8) 0.0661(2) Uani 1 1 d . . .
N1 N 1.3174(2) 0.32747(19) 0.86272(17) 0.0366(4) Uani 1 1 d . . .
N2 N 1.1018(2) 0.14437(19) 0.76456(17) 0.0348(4) Uani 1 1 d . . .
N3 N 1.1208(3) 0.1735(2) 0.66851(19) 0.0492(5) Uani 1 1 d . . .
O1 O 1.2511(3) 0.6057(2) 1.05280(19) 0.0583(5) Uani 1 1 d . . .
O2 O 1.4157(2) 0.48410(17) 1.12681(15) 0.0432(4) Uani 1 1 d . . .
O3 O 0.9063(2) 0.17898(18) 0.91559(17) 0.0481(4) Uani 1 1 d . . .
H3 H 0.8683 0.2490 0.9292 0.072 Uiso 1 1 calc R U .
O4 O 1.0281(2) -0.05660(16) 0.79474(15) 0.0378(4) Uani 1 1 d . . .
C1 C 1.2519(3) 0.2842(3) 0.7326(2) 0.0483(6) Uani 1 1 d . . .
H1 H 1.2962 0.3293 0.6920 0.058 Uiso 1 1 calc R U .
C2 C 1.2190(3) 0.2365(2) 0.8789(2) 0.0362(5) Uani 1 1 d . . .
H2 H 1.2302 0.2370 0.9585 0.043 Uiso 1 1 calc R U .
C3 C 0.9610(3) 0.0285(2) 0.7350(2) 0.0355(5) Uani 1 1 d . . .
H3A H 0.9072 -0.0286 0.6407 0.043 Uiso 1 1 calc R U .
C4 C 0.8273(3) 0.0856(2) 0.7827(2) 0.0417(6) Uani 1 1 d . . .
H4 H 0.7838 0.1424 0.7367 0.050 Uiso 1 1 calc R U .
C5 C 0.6714(3) -0.0301(3) 0.7510(3) 0.0568(7) Uani 1 1 d . . .
C6 C 0.6044(4) -0.1354(4) 0.6062(4) 0.0821(11) Uani 1 1 d . . .
H6A H 0.6907 -0.1817 0.5905 0.123 Uiso 1 1 calc R U .
H6B H 0.5043 -0.2048 0.5849 0.123 Uiso 1 1 calc R U .
H6C H 0.5764 -0.0852 0.5531 0.123 Uiso 1 1 calc R U .
C7 C 0.7134(5) -0.1082(4) 0.8382(4) 0.0829(11) Uani 1 1 d . . .
H7A H 0.8000 -0.1552 0.8246 0.124 Uiso 1 1 calc R U .
H7B H 0.7537 -0.0414 0.9277 0.124 Uiso 1 1 calc R U .
H7C H 0.6126 -0.1769 0.8168 0.124 Uiso 1 1 calc R U .
C8 C 0.5345(4) 0.0426(4) 0.7750(4) 0.0893(13) Uani 1 1 d . . .
H8A H 0.5062 0.0922 0.7214 0.134 Uiso 1 1 calc R U .
H8B H 0.4348 -0.0269 0.7540 0.134 Uiso 1 1 calc R U .
H8C H 0.5759 0.1086 0.8649 0.134 Uiso 1 1 calc R U .
C9 C 1.0924(3) -0.1616(2) 0.7294(2) 0.0331(5) Uani 1 1 d . . .
C10 C 1.0887(3) -0.1937(3) 0.6072(2) 0.0414(5) Uani 1 1 d . . .
H10 H 1.0430 -0.1419 0.5625 0.050 Uiso 1 1 calc R U .
C11 C 1.1538(3) -0.3043(3) 0.5508(2) 0.0445(6) Uani 1 1 d . . .
H11 H 1.1485 -0.3289 0.4669 0.053 Uiso 1 1 calc R U .
C12 C 1.2257(3) -0.3771(2) 0.6189(2) 0.0430(6) Uani 1 1 d . . .
C13 C 1.2310(4) -0.3440(3) 0.7419(3) 0.0544(7) Uani 1 1 d . . .
H13 H 1.2804 -0.3938 0.7876 0.065 Uiso 1 1 calc R U .
C14 C 1.1630(4) -0.2371(3) 0.7969(2) 0.0478(6) Uani 1 1 d . . .
H14 H 1.1644 -0.2154 0.8794 0.057 Uiso 1 1 calc R U .
C15 C 1.2934(3) 0.5447(3) 1.1235(2) 0.0463(6) Uani 1 1 d . . .
C16 C 1.2035(5) 0.5361(4) 1.2088(4) 0.0820(11) Uani 1 1 d . . .
H16A H 1.2544 0.4848 1.2561 0.123 Uiso 1 1 calc R U .
H16B H 1.2130 0.6299 1.2688 0.123 Uiso 1 1 calc R U .
H16C H 1.0854 0.4881 1.1562 0.123 Uiso 1 1 calc R U .
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'
Cl Cl 0.1484 0.1585 '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'
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
O2 Cu1 O2 180.00(4) . 2_867
O2 Cu1 N1 90.87(7) . 2_867
O2 Cu1 N1 89.13(7) 2_867 2_867
O2 Cu1 N1 89.13(7) . .
O2 Cu1 N1 90.87(7) 2_867 .
N1 Cu1 N1 180.00(12) 2_867 .
C2 N1 C1 103.24(19) . .
C2 N1 Cu1 127.70(16) . .
C1 N1 Cu1 128.70(16) . .
C2 N2 N3 110.13(19) . .
C2 N2 C3 129.13(19) . .
N3 N2 C3 120.68(17) . .
C1 N3 N2 102.51(18) . .
C15 O2 Cu1 108.12(16) . .
C4 O3 H3 109.5 . .
C9 O4 C3 118.06(17) . .
N3 C1 N1 114.4(2) . .
N3 C1 H1 122.8 . .
N1 C1 H1 122.8 . .
N1 C2 N2 109.7(2) . .
N1 C2 H2 125.1 . .
N2 C2 H2 125.1 . .
O4 C3 N2 108.56(17) . .
O4 C3 C4 110.21(19) . .
N2 C3 C4 111.15(18) . .
O4 C3 H3A 109.0 . .
N2 C3 H3A 109.0 . .
C4 C3 H3A 109.0 . .
O3 C4 C3 109.48(18) . .
O3 C4 C5 112.9(2) . .
C3 C4 C5 114.3(2) . .
O3 C4 H4 106.5 . .
C3 C4 H4 106.5 . .
C5 C4 H4 106.5 . .
C8 C5 C7 108.0(3) . .
C8 C5 C6 109.2(3) . .
C7 C5 C6 110.6(3) . .
C8 C5 C4 107.5(2) . .
C7 C5 C4 112.4(2) . .
C6 C5 C4 109.1(3) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 O4 124.9(2) . .
C10 C9 C14 120.4(2) . .
O4 C9 C14 114.7(2) . .
C9 C10 C11 119.3(2) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
C12 C11 C10 120.0(2) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 120.7(2) . .
C11 C12 Cl1 118.65(19) . .
C13 C12 Cl1 120.6(2) . .
C12 C13 C14 119.6(2) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
C13 C14 C9 120.0(2) . .
C13 C14 H14 120.0 . .
C9 C14 H14 120.0 . .
O1 C15 O2 121.8(2) . .
O1 C15 C16 121.7(3) . .
O2 C15 C16 116.4(3) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.9410(16) .
Cu1 O2 1.9410(16) 2_867
Cu1 N1 1.9950(18) 2_867
Cu1 N1 1.9950(18) .
Cl1 C12 1.741(2) .
N1 C2 1.320(3) .
N1 C1 1.350(3) .
N2 C2 1.324(3) .
N2 N3 1.354(3) .
N2 C3 1.470(3) .
N3 C1 1.308(3) .
O1 C15 1.234(3) .
O2 C15 1.282(3) .
O3 C4 1.406(3) .
O3 H3 0.8200 .
O4 C9 1.384(3) .
O4 C3 1.403(3) .
C1 H1 0.9300 .
C2 H2 0.9300 .
C3 C4 1.526(3) .
C3 H3A 0.9800 .
C4 C5 1.549(4) .
C4 H4 0.9800 .
C5 C8 1.516(4) .
C5 C7 1.538(5) .
C5 C6 1.544(4) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.372(3) .
C9 C14 1.385(3) .
C10 C11 1.389(3) .
C10 H10 0.9300 .
C11 C12 1.369(4) .
C11 H11 0.9300 .
C12 C13 1.375(4) .
C13 C14 1.374(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.492(4) .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
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
C2 N2 N3 C1 0.1(3)
C3 N2 N3 C1 177.3(2)
N2 N3 C1 N1 0.0(3)
C2 N1 C1 N3 0.0(3)
Cu1 N1 C1 N3 -173.44(18)
C1 N1 C2 N2 0.1(3)
Cu1 N1 C2 N2 173.56(14)
N3 N2 C2 N1 -0.1(3)
C3 N2 C2 N1 -177.1(2)
C9 O4 C3 N2 -84.6(2)
C9 O4 C3 C4 153.44(18)
C2 N2 C3 O4 -53.4(3)
N3 N2 C3 O4 129.9(2)
C2 N2 C3 C4 68.0(3)
N3 N2 C3 C4 -108.7(2)
O4 C3 C4 O3 66.3(2)
N2 C3 C4 O3 -54.1(3)
O4 C3 C4 C5 -61.6(3)
N2 C3 C4 C5 178.0(2)
O3 C4 C5 C8 67.2(3)
C3 C4 C5 C8 -166.8(3)
O3 C4 C5 C7 -51.5(3)
C3 C4 C5 C7 74.5(3)
O3 C4 C5 C6 -174.6(2)
C3 C4 C5 C6 -48.5(3)
C3 O4 C9 C10 -3.2(3)
C3 O4 C9 C14 177.3(2)
O4 C9 C10 C11 -178.3(2)
C14 C9 C10 C11 1.1(4)
C9 C10 C11 C12 -2.1(4)
C10 C11 C12 C13 1.5(4)
C10 C11 C12 Cl1 -177.05(19)
C11 C12 C13 C14 0.2(4)
Cl1 C12 C13 C14 178.7(2)
C12 C13 C14 C9 -1.2(4)
C10 C9 C14 C13 0.5(4)
O4 C9 C14 C13 -180.0(2)
Cu1 O2 C15 O1 -3.0(3)
Cu1 O2 C15 C16 176.3(2)
