#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/86/2208602.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_2208602
loop_
_publ_author_name
'Ali, Hapipah M.'
'Abdul Halim, Siti Nadiah'
'Ng, Seik Weng'
_publ_section_title
;Bis(5-bromo-1H-indole-3-carbaldehyde
 2-nitrobenzoylhydrazonato-κ²N,O)bis(N,N-dimethylformamide-κO)copper(II)
;
_journal_coeditor_code           HB2016
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m724
_journal_page_last               m725
_journal_paper_doi               10.1107/S1600536806007616
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C16 H10 Br N4 O3)2 (C3 H7 N O)2]'
_chemical_formula_moiety         'C38 H34 Br2 Cu N10 O8'
_chemical_formula_sum            'C38 H34 Br2 Cu N10 O8'
_chemical_formula_weight         982.11
_chemical_name_systematic
;
Bis(5-bromo-1H-indole-3-carbaldehyde 2-nitrobenzoylhydrazonato-
κ²N,O)bis(N,N-dimethylformamide-\kO)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   mixed
_atom_sites_solution_primary     'Cu atom placed at 1/2, 1/2, 1/2'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.84(2)
_cell_angle_beta                 99.270(10)
_cell_angle_gamma                106.430(10)
_cell_formula_units_Z            1
_cell_length_a                   8.643(5)
_cell_length_b                   9.102(5)
_cell_length_c                   14.302(9)
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.4
_cell_volume                     1036.9(11)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'CrystalStructure (Rigaku/MSC, 2005)'
_diffrn_ambient_temperature      295(3)
_diffrn_detector_area_resol_mean 13.65
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.037
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17658
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.517
_exptl_absorpt_correction_T_max  0.686
_exptl_absorpt_correction_T_min  0.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             495
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.055
_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)+(0.1064P)²+0.1574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.160
_refine_ls_wR_factor_ref         0.180
_reflns_number_gt                2915
_reflns_number_total             3797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2016.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        1037.0(10)
_cod_database_code               2208602
_cod_database_fobs_code          2208602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
Br Br1 0.29765(9) 1.06647(7) 0.95543(3) 0.0955(3) Uani d . 1
Cu Cu1 0.5000 0.5000 0.5000 0.0468(2) Uani d S 1
O O1 0.4860(3) 0.5059(3) 0.3647(2) 0.0540(10) Uani d . 1
O O2 0.5973(5) 0.3978(5) 0.1791(3) 0.0960(10) Uani d . 1
O O3 0.3561(5) 0.2577(4) 0.1874(3) 0.0870(10) Uani d . 1
O O4 0.1452(4) 0.2901(4) 0.4329(3) 0.0830(10) Uani d . 1
N N1 0.4541(5) 0.3808(5) 0.1808(2) 0.0650(10) Uani d . 1
N N2 0.3812(4) 0.7082(3) 0.4090(2) 0.0460(10) Uani d . 1
N N3 0.4216(4) 0.6795(3) 0.5011(2) 0.0440(10) Uani d . 1
N N4 0.2160(4) 1.0726(4) 0.5329(2) 0.0530(10) Uani d D 1
N N5 0.0272(4) 0.3587(5) 0.3019(3) 0.0740(10) Uani d . 1
C C1 0.3896(5) 0.5105(5) 0.1646(3) 0.0530(10) Uani d . 1
C C2 0.3428(6) 0.5127(7) 0.0685(3) 0.0720(10) Uani d . 1
C C3 0.2820(7) 0.6296(7) 0.0465(3) 0.084(2) Uani d . 1
C C4 0.2684(7) 0.7407(6) 0.1209(3) 0.0780(10) Uani d . 1
C C5 0.3137(6) 0.7362(5) 0.2170(3) 0.0620(10) Uani d . 1
C C6 0.3764(5) 0.6184(4) 0.2419(3) 0.0460(10) Uani d . 1
C C7 0.4193(4) 0.6104(4) 0.3454(3) 0.0450(10) Uani d . 1
C C8 0.3941(4) 0.7669(4) 0.5735(2) 0.0430(10) Uani d . 1
C C9 0.2773(4) 0.9596(4) 0.5002(3) 0.0480(10) Uani d . 1
C C10 0.3261(4) 0.8926(4) 0.5750(3) 0.0440(10) Uani d . 1
C C11 0.2921(4) 0.9755(4) 0.6603(3) 0.0440(10) Uani d . 1
C C12 0.3158(5) 0.9696(4) 0.7588(3) 0.0530(10) Uani d . 1
C C13 0.2653(6) 1.0696(5) 0.8204(3) 0.0630(10) Uani d . 1
C C14 0.1935(7) 1.1778(6) 0.7900(4) 0.0790(10) Uani d . 1
C C15 0.1717(6) 1.1878(5) 0.6955(4) 0.0700(10) Uani d . 1
C C16 0.2227(5) 1.0870(4) 0.6306(3) 0.0510(10) Uani d . 1
C C17 0.1028(6) 0.2731(6) 0.3438(4) 0.0730(10) Uani d . 1
C C18 -0.0207(8) 0.4752(8) 0.3585(6) 0.117(2) Uani d . 1
C C19 -0.0172(7) 0.3340(10) 0.1964(5) 0.118(3) Uani d . 1
H H4n 0.178(6) 1.123(6) 0.495(3) 0.10(2) Uiso d D 1
H H2 0.3521 0.4366 0.0194 0.086 Uiso calc R 1
H H3 0.2502 0.6340 -0.0180 0.101 Uiso calc R 1
H H4 0.2279 0.8202 0.1058 0.094 Uiso calc R 1
H H5 0.3025 0.8119 0.2657 0.075 Uiso calc R 1
H H8 0.4230 0.7445 0.6337 0.052 Uiso calc R 1
H H9 0.2860 0.9300 0.4363 0.058 Uiso calc R 1
H H12 0.3645 0.8998 0.7815 0.064 Uiso calc R 1
H H14 0.1605 1.2430 0.8345 0.094 Uiso calc R 1
H H15 0.1244 1.2596 0.6744 0.084 Uiso calc R 1
H H17 0.1262 0.1940 0.3038 0.087 Uiso calc R 1
H H18a -0.0239 0.4543 0.4218 0.175 Uiso calc R 1
H H18b -0.1283 0.4732 0.3270 0.175 Uiso calc R 1
H H18c 0.0578 0.5770 0.3649 0.175 Uiso calc R 1
H H19a 0.0277 0.2574 0.1668 0.177 Uiso calc R 1
H H19b 0.0269 0.4315 0.1780 0.177 Uiso calc R 1
H H19c -0.1355 0.2970 0.1748 0.177 Uiso calc R 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'
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'
Br Br -0.2901 2.4595 '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 no
O1 Cu1 O4 . . 85.00(10) yes
O1 Cu1 N3 . . 81.80(10) yes
O1 Cu1 N3 . 2_666 98.20(10) yes
O1 Cu1 N3 2_666 . 98.20(10) no
O1 Cu1 N3 2_666 2_666 81.80(10) no
O1 Cu1 O4 2_666 . 95.00(10) no
N3 Cu1 N3 . 2_666 180 no
N3 Cu1 O4 . . 88.40(10) yes
N3 Cu1 O4 2_666 . 91.70(10) yes
O1 Cu1 O4 . 2_666 95.00(10) no
O1 Cu1 O4 2_666 2_666 85.00(10) no
N3 Cu1 O4 . 2_666 91.70(10) no
N3 Cu1 O4 2_666 2_666 88.40(10) no
O4 Cu1 O4 . 2_666 180 no
C7 O1 Cu1 . . 109.4(2) no
C17 O4 Cu1 . . 108.5(3) no
O2 N1 O3 . . 123.7(4) no
O2 N1 C1 . . 117.9(4) no
O3 N1 C1 . . 118.1(4) no
C7 N2 N3 . . 109.1(3) no
C8 N3 N2 . . 117.7(3) no
C8 N3 Cu1 . . 128.6(2) no
N2 N3 Cu1 . . 113.5(2) no
C9 N4 C16 . . 109.8(3) no
C17 N5 C18 . . 120.6(5) no
C17 N5 C19 . . 121.7(5) no
C18 N5 C19 . . 117.6(5) no
C2 C1 C6 . . 124.0(4) no
C2 C1 N1 . . 114.6(4) no
C6 C1 N1 . . 121.4(3) no
C3 C2 C1 . . 118.7(5) no
C2 C3 C4 . . 119.5(4) no
C5 C4 C3 . . 121.3(4) no
C4 C5 C6 . . 120.6(4) no
C1 C6 C5 . . 115.9(3) no
C1 C6 C7 . . 123.7(3) no
C5 C6 C7 . . 120.4(4) no
O1 C7 N2 . . 125.7(3) no
O1 C7 C6 . . 117.8(3) no
N2 C7 C6 . . 116.6(3) no
N3 C8 C10 . . 129.6(3) no
N4 C9 C10 . . 110.4(3) no
C9 C10 C8 . . 130.0(3) no
C9 C10 C11 . . 105.6(3) no
C8 C10 C11 . . 124.4(3) no
C12 C11 C16 . . 118.5(3) no
C12 C11 C10 . . 134.9(3) no
C16 C11 C10 . . 106.6(3) no
C13 C12 C11 . . 118.1(4) no
C12 C13 C14 . . 123.0(4) no
C12 C13 Br1 . . 119.3(3) no
C14 C13 Br1 . . 117.7(3) no
C15 C14 C13 . . 120.1(4) no
C14 C15 C16 . . 118.2(4) no
N4 C16 C15 . . 130.3(4) no
N4 C16 C11 . . 107.6(3) no
C15 C16 C11 . . 122.1(4) no
O4 C17 N5 . . 124.5(5) no
C9 N4 H4n . . 122(4) no
C16 N4 H4n . . 129(4) no
C3 C2 H2 . . 120.7 no
C1 C2 H2 . . 120.7 no
C2 C3 H3 . . 120.2 no
C4 C3 H3 . . 120.2 no
C5 C4 H4 . . 119.3 no
C3 C4 H4 . . 119.3 no
C4 C5 H5 . . 119.7 no
C6 C5 H5 . . 119.7 no
N3 C8 H8 . . 115.2 no
C10 C8 H8 . . 115.2 no
N4 C9 H9 . . 124.8 no
C10 C9 H9 . . 124.8 no
C13 C12 H12 . . 121.0 no
C11 C12 H12 . . 121.0 no
C15 C14 H14 . . 120.0 no
C13 C14 H14 . . 120.0 no
C14 C15 H15 . . 120.9 no
C16 C15 H15 . . 120.9 no
O4 C17 H17 . . 117.8 no
N5 C17 H17 . . 117.8 no
N5 C18 H18a . . 109.5 no
N5 C18 H18b . . 109.5 no
H18a C18 H18b . . 109.5 no
N5 C18 H18c . . 109.5 no
H18a C18 H18c . . 109.5 no
H18b C18 H18c . . 109.5 no
N5 C19 H19a . . 109.5 no
N5 C19 H19b . . 109.5 no
H19a C19 H19b . . 109.5 no
N5 C19 H19c . . 109.5 no
H19a C19 H19c . . 109.5 no
H19b C19 H19c . . 109.5 no
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
C13 Br1 . 1.912(5) no
Cu1 O1 . 1.930(3) yes
Cu1 O1 2_666 1.930(3) no
Cu1 O4 . 3.014(4) yes
Cu1 O4 2_666 3.014(4) no
Cu1 N3 . 1.937(3) yes
Cu1 N3 2_666 1.937(3) no
O1 C7 . 1.289(4) no
O2 N1 . 1.208(5) no
O3 N1 . 1.227(5) no
O4 C17 . 1.239(6) no
N1 C1 . 1.478(5) no
N2 C7 . 1.308(5) no
N2 N3 . 1.395(4) no
N3 C8 . 1.291(5) no
N4 C9 . 1.334(5) no
N4 C16 . 1.371(5) no
N5 C17 . 1.309(5) no
N5 C18 . 1.419(8) no
N5 C19 . 1.458(7) no
C1 C2 . 1.373(6) no
C1 C6 . 1.390(6) no
C2 C3 . 1.373(7) no
C3 C4 . 1.381(7) no
C4 C5 . 1.378(6) no
C5 C6 . 1.403(5) no
C6 C7 . 1.486(5) no
C8 C10 . 1.426(5) no
C9 C10 . 1.384(5) no
C10 C11 . 1.438(5) no
C11 C12 . 1.403(5) no
C11 C16 . 1.407(5) no
C12 C13 . 1.368(6) no
C13 C14 . 1.396(6) no
C14 C15 . 1.356(7) no
C15 C16 . 1.403(6) no
N4 H4n . 0.850(10) no
C2 H2 . 0.93 no
C3 H3 . 0.93 no
C4 H4 . 0.93 no
C5 H5 . 0.93 no
C8 H8 . 0.93 no
C9 H9 . 0.93 no
C12 H12 . 0.93 no
C14 H14 . 0.93 no
C15 H15 . 0.93 no
C17 H17 . 0.93 no
C18 H18a . 0.96 no
C18 H18b . 0.96 no
C18 H18c . 0.96 no
C19 H19a . 0.96 no
C19 H19b . 0.96 no
C19 H19c . 0.96 no
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
_geom_hbond_publ_flag
N4 H4n O4 1_565 0.850(10) 1.95(2) 2.777(4) 163(5) yes
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
_geom_torsion_publ_flag
N3 Cu1 O1 C7 . -6.2(2) no
N3 Cu1 O1 C7 2_666 173.8(2) no
O4 Cu1 O1 C7 . 82.8(2) no
O1 Cu1 O4 C17 2_666 -179.7(3) no
O1 Cu1 O4 C17 . 0.3(3) no
N3 Cu1 O4 C17 . 82.1(3) no
N3 Cu1 O4 C17 2_666 -97.9(3) no
C7 N2 N3 C8 . 179.2(3) no
C7 N2 N3 Cu1 . -4.6(3) no
O1 Cu1 N3 C8 2_666 1.8(3) no
O1 Cu1 N3 C8 . -178.2(3) no
O4 Cu1 N3 C8 . 96.6(3) no
O1 Cu1 N3 N2 2_666 -173.9(2) no
O1 Cu1 N3 N2 . 6.1(2) no
O4 Cu1 N3 N2 . -79.0(2) no
O2 N1 C1 C2 . 82.3(5) no
O3 N1 C1 C2 . -92.0(5) no
O2 N1 C1 C6 . -98.7(5) no
O3 N1 C1 C6 . 87.0(5) no
C6 C1 C2 C3 . 1.3(8) no
N1 C1 C2 C3 . -179.7(5) no
C1 C2 C3 C4 . -0.4(8) no
C2 C3 C4 C5 . -0.4(9) no
C3 C4 C5 C6 . 0.5(8) no
C2 C1 C6 C5 . -1.2(6) no
N1 C1 C6 C5 . 179.9(4) no
C2 C1 C6 C7 . 176.8(4) no
N1 C1 C6 C7 . -2.1(6) no
C4 C5 C6 C1 . 0.3(6) no
C4 C5 C6 C7 . -177.8(4) no
Cu1 O1 C7 N2 . 6.0(5) no
Cu1 O1 C7 C6 . -171.9(3) no
N3 N2 C7 O1 . -1.0(5) no
N3 N2 C7 C6 . 176.9(3) no
C1 C6 C7 O1 . 6.3(6) no
C5 C6 C7 O1 . -175.8(4) no
C1 C6 C7 N2 . -171.8(4) no
C5 C6 C7 N2 . 6.1(5) no
N2 N3 C8 C10 . 0.2(6) no
Cu1 N3 C8 C10 . -175.3(3) no
C16 N4 C9 C10 . 0.6(4) no
N4 C9 C10 C8 . 178.4(4) no
N4 C9 C10 C11 . -0.7(4) no
N3 C8 C10 C9 . -3.0(7) no
N3 C8 C10 C11 . 176.0(4) no
C9 C10 C11 C12 . -177.8(4) no
C8 C10 C11 C12 . 3.0(7) no
C9 C10 C11 C16 . 0.6(4) no
C8 C10 C11 C16 . -178.6(3) no
C16 C11 C12 C13 . 2.0(6) no
C10 C11 C12 C13 . -179.7(4) no
C11 C12 C13 C14 . -0.8(7) no
C11 C12 C13 Br1 . -179.4(3) no
C12 C13 C14 C15 . -0.4(8) no
Br1 C13 C14 C15 . 178.2(4) no
C13 C14 C15 C16 . 0.2(8) no
C9 N4 C16 C15 . -179.4(5) no
C9 N4 C16 C11 . -0.2(4) no
C14 C15 C16 N4 . -179.8(5) no
C14 C15 C16 C11 . 1.1(7) no
C12 C11 C16 N4 . 178.5(3) no
C10 C11 C16 N4 . -0.2(4) no
C12 C11 C16 C15 . -2.3(6) no
C10 C11 C16 C15 . 179.0(4) no
Cu1 O4 C17 N5 . -94.4(5) no
C18 N5 C17 O4 . -3.7(8) no
C19 N5 C17 O4 . 179.1(5) no
