#------------------------------------------------------------------------------
#$Date: 2020-10-21 08:06:42 +0300 (Wed, 21 Oct 2020) $
#$Revision: 258510 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243630.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_2243630
loop_
_publ_author_name
'de Melo, Ana Paula Lopes'
'Bresolin, Leandro'
'Martins, Bianca Barreto'
'Gervini, Vanessa Carratu'
'de Oliveira, Adriano Bof'
_publ_section_title
;
 Crystal structure and Hirshfeld analysis of
 trans-bis(5-fluoroindoline-2,3-dione
 3-oximato-κ²O²,N³)-trans-bis(pyridine-κN)copper(II)
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              428
_journal_page_last               432
_journal_paper_doi               10.1107/S2056989018003365
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '[Cu (C8 H4 F1 N2 O2)2 (C5 H5 N1)2]'
_chemical_formula_moiety         'C26 H18 Cu F2 N6 O4'
_chemical_formula_sum            'C26 H18 Cu F2 N6 O4'
_chemical_formula_weight         580.00
_chemical_name_systematic
'trans-Bis(5-fluoroindoline-2,3-dione 3-oximato-κ²O²,N³)-trans-bis(pyridine-κN)copper(II)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.579(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9709(14)
_cell_length_b                   7.2155(5)
_cell_length_c                   17.1989(12)
_cell_measurement_reflns_used    9537
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.67
_cell_measurement_theta_min      2.40
_cell_volume                     2450.6(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
WinGX (Farrugia, 2012), DIAMOND (Brandenburg, 2006) and
CrystalExplorer (Wolff et al., 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and enCIFer (Allen et al.,
2004)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.672
_diffrn_reflns_theta_min         2.063
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.337
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0326
_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)+(0.0350P)²+2.8170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                3966
_reflns_number_total             4481
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rz5228sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243630
_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   0.702
_shelx_estimated_absorpt_t_max   0.832
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.66193(6) 0.43044(17) 0.51144(7) 0.0202(2) Uani d 1 . .
C C2 0.62981(6) 0.59529(16) 0.54136(7) 0.0179(2) Uani d 1 . .
C C3 0.57200(6) 0.53285(17) 0.57616(7) 0.0190(2) Uani d 1 . .
C C4 0.52421(7) 0.6220(2) 0.61397(8) 0.0252(2) Uani d 1 . .
H H1 0.524139 0.752687 0.620565 0.030 Uiso calc 1 . .
C C5 0.47665(7) 0.5092(2) 0.64150(10) 0.0308(3) Uani d 1 . .
C C6 0.47458(7) 0.3189(2) 0.63286(10) 0.0330(3) Uani d 1 . .
H H2 0.440637 0.248844 0.652851 0.040 Uiso calc 1 . .
C C7 0.52236(8) 0.2300(2) 0.59479(10) 0.0292(3) Uani d 1 . .
H H3 0.521610 0.099354 0.587721 0.035 Uiso calc 1 . .
C C8 0.57102(6) 0.33887(17) 0.56761(8) 0.0213(2) Uani d 1 . .
C C9 0.79324(7) 0.8070(2) 0.66905(8) 0.0271(3) Uani d 1 . .
H H5 0.778142 0.929489 0.656022 0.033 Uiso calc 1 . .
C C10 0.81834(9) 0.7655(3) 0.74669(9) 0.0361(3) Uani d 1 . .
H H6 0.820299 0.858192 0.786181 0.043 Uiso calc 1 . .
C C11 0.84039(8) 0.5880(3) 0.76578(9) 0.0374(4) Uani d 1 . .
H H7 0.857425 0.556392 0.818653 0.045 Uiso calc 1 . .
C C12 0.83737(9) 0.4571(3) 0.70703(10) 0.0359(3) Uani d 1 . .
H H8 0.852688 0.334216 0.718775 0.043 Uiso calc 1 . .
C C13 0.81167(8) 0.5072(2) 0.63051(9) 0.0285(3) Uani d 1 . .
H H9 0.809607 0.416673 0.590100 0.034 Uiso calc 1 . .
Cu Cu1 0.750000 0.750000 0.500000 0.01704(6) Uani d 1 . .
F F1 0.42924(6) 0.59199(17) 0.67886(8) 0.0505(3) Uani d 1 . .
N N1 0.62487(6) 0.28139(15) 0.52904(8) 0.0242(2) Uani d 1 . .
H H4 0.633443 0.165583 0.517849 0.029 Uiso calc 1 . .
N N2 0.65751(5) 0.75711(14) 0.53373(6) 0.01704(17) Uani d 1 . .
N N3 0.78961(5) 0.67952(17) 0.61181(6) 0.0208(2) Uani d 1 . .
O O1 0.71204(5) 0.42959(14) 0.47722(6) 0.02501(19) Uani d 1 . .
O O2 0.62959(5) 0.90531(12) 0.55624(6) 0.02333(18) Uani d 1 . .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 127.37(12) ?
O1 C1 C2 . . 126.46(12) ?
N1 C1 C2 . . 106.18(11) ?
N2 C2 C3 . . 133.98(11) ?
N2 C2 C1 . . 118.12(10) ?
C3 C2 C1 . . 107.89(10) ?
C4 C3 C8 . . 120.61(12) ?
C4 C3 C2 . . 133.96(12) ?
C8 C3 C2 . . 105.40(11) ?
C5 C4 C3 . . 116.20(13) ?
C5 C4 H1 . . 121.9 ?
C3 C4 H1 . . 121.9 ?
F1 C5 C6 . . 118.42(13) ?
F1 C5 C4 . . 117.69(14) ?
C6 C5 C4 . . 123.89(14) ?
C5 C6 C7 . . 119.82(13) ?
C5 C6 H2 . . 120.1 ?
C7 C6 H2 . . 120.1 ?
C8 C7 C6 . . 117.53(13) ?
C8 C7 H3 . . 121.2 ?
C6 C7 H3 . . 121.2 ?
C7 C8 C3 . . 121.93(13) ?
C7 C8 N1 . . 128.03(12) ?
C3 C8 N1 . . 110.04(11) ?
N3 C9 C10 . . 122.06(15) ?
N3 C9 H5 . . 119.0 ?
C10 C9 H5 . . 119.0 ?
C11 C10 C9 . . 119.13(15) ?
C11 C10 H6 . . 120.4 ?
C9 C10 H6 . . 120.4 ?
C10 C11 C12 . . 119.00(14) ?
C10 C11 H7 . . 120.5 ?
C12 C11 H7 . . 120.5 ?
C11 C12 C13 . . 119.13(15) ?
C11 C12 H8 . . 120.4 ?
C13 C12 H8 . . 120.4 ?
N3 C13 C12 . . 122.02(15) ?
N3 C13 H9 . . 119.0 ?
C12 C13 H9 . . 119.0 ?
N2 Cu1 N3 . . 88.75(4) ?
O1 Cu1 N3 . . 89.01(4) ?
C1 N1 C8 . . 110.49(10) ?
C1 N1 H4 . . 124.8 ?
C8 N1 H4 . . 124.8 ?
O2 N2 C2 . . 120.09(10) ?
O2 N2 Cu1 . . 124.18(8) ?
C2 N2 Cu1 . . 115.18(8) ?
C9 N3 C13 . . 118.66(12) ?
C9 N3 Cu1 . . 119.59(10) ?
C13 N3 Cu1 . . 121.74(10) ?
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
C1 O1 . 1.2342(15) ?
C1 N1 . 1.3649(16) ?
C1 C2 . 1.4798(17) ?
C2 N2 . 1.3070(15) ?
C2 C3 . 1.4493(16) ?
C3 C4 . 1.3901(18) ?
C3 C8 . 1.4072(17) ?
C4 C5 . 1.386(2) ?
C4 H1 . 0.9500 ?
C5 F1 . 1.3591(17) ?
C5 C6 . 1.382(2) ?
C6 C7 . 1.392(2) ?
C6 H2 . 0.9500 ?
C7 C8 . 1.3841(18) ?
C7 H3 . 0.9500 ?
C8 N1 . 1.4077(17) ?
C9 N3 . 1.3412(19) ?
C9 C10 . 1.387(2) ?
C9 H5 . 0.9500 ?
C10 C11 . 1.378(3) ?
C10 H6 . 0.9500 ?
C11 C12 . 1.378(3) ?
C11 H7 . 0.9500 ?
C12 C13 . 1.387(2) ?
C12 H8 . 0.9500 ?
C13 N3 . 1.3423(19) ?
C13 H9 . 0.9500 ?
Cu1 N2 . 2.0176(10) ?
Cu1 N3 . 2.0319(11) ?
N1 H4 . 0.8800 ?
N2 O2 . 1.2917(13) ?
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
C9 H5 O1 7_666 0.95 2.54 3.1424(18) 121.4
C12 H8 F1 3_545 0.95 2.49 3.287(2) 142.2
C13 H9 O1 1 0.95 2.54 3.1077(19) 118.6
N1 H4 O2 1_545 0.88 2.00 2.7529(14) 143.4
C6 H2 Cg1 3_445 0.95 2.79 3.7076(17) 161.6
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 N2 . . . . -2.32(19) ?
N1 C1 C2 N2 . . . . 177.94(12) ?
O1 C1 C2 C3 . . . . 179.09(13) ?
N1 C1 C2 C3 . . . . -0.65(14) ?
N2 C2 C3 C4 . . . . 0.5(3) ?
C1 C2 C3 C4 . . . . 178.76(14) ?
N2 C2 C3 C8 . . . . -177.63(14) ?
C1 C2 C3 C8 . . . . 0.63(13) ?
C8 C3 C4 C5 . . . . -0.3(2) ?
C2 C3 C4 C5 . . . . -178.20(14) ?
C3 C4 C5 F1 . . . . 179.91(13) ?
C3 C4 C5 C6 . . . . -0.4(2) ?
F1 C5 C6 C7 . . . . 179.92(15) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
C5 C6 C7 C8 . . . . 0.6(2) ?
C6 C7 C8 C3 . . . . -1.3(2) ?
C6 C7 C8 N1 . . . . 178.68(14) ?
C4 C3 C8 C7 . . . . 1.2(2) ?
C2 C3 C8 C7 . . . . 179.62(13) ?
C4 C3 C8 N1 . . . . -178.83(12) ?
C2 C3 C8 N1 . . . . -0.40(14) ?
N3 C9 C10 C11 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . 0.5(3) ?
C10 C11 C12 C13 . . . . -0.6(3) ?
C11 C12 C13 N3 . . . . 0.0(2) ?
O1 C1 N1 C8 . . . . -179.33(13) ?
C2 C1 N1 C8 . . . . 0.41(14) ?
C7 C8 N1 C1 . . . . 179.97(14) ?
C3 C8 N1 C1 . . . . -0.01(16) ?
C3 C2 N2 O2 . . . . -4.6(2) ?
C1 C2 N2 O2 . . . . 177.27(11) ?
C3 C2 N2 Cu1 . . . . 167.30(11) ?
C1 C2 N2 Cu1 . . . . -10.83(14) ?
C10 C9 N3 C13 . . . . -0.7(2) ?
C10 C9 N3 Cu1 . . . . 178.48(12) ?
C12 C13 N3 C9 . . . . 0.6(2) ?
C12 C13 N3 Cu1 . . . . -178.54(12) ?

_cod_database_fobs_code 2243630
