#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:13:15 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179744 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/40/7004085.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_7004085
loop_
_publ_author_name
'Bates, Gareth W.'
'Gale, Philip A.'
'Light, Mark E.'
'Ogden, Mark I.'
'Warriner, Colin N.'
_publ_section_title
;
 Structural diversity in the first metal complexes of
 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles
;
_journal_issue                   31
_journal_name_full               'Dalton Transactions'
_journal_page_first              4106
_journal_page_last               4112
_journal_paper_doi               10.1039/b802506a
_journal_year                    2008
_chemical_formula_sum            'C66 H58 K4 N14 Ni O27'
_chemical_formula_weight         1694.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.6020(10)
_cell_length_b                   15.6020(10)
_cell_length_c                   15.9970(6)
_cell_measurement_reflns_used    4267
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     3894.0(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.1133
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16842
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.8879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Dark Orange'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.270
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4460
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0797
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1126P)²+6.6118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2307
_reflns_number_gt                2732
_reflns_number_total             4460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802506a.txt
_cod_data_source_block           2005sot1251
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 
;
_cod_original_sg_symbol_H-M      P4(2)/n
_cod_database_code               7004085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.2500 0.2500 0.7500 0.01651(10) Uani 1 4 d S . .
K1 K 0.31066(3) 0.52143(3) 1.03425(3) 0.02782(12) Uani 1 1 d . . .
N1 N 0.41968(11) 0.42546(11) 0.50691(10) 0.0302(5) Uani 1 1 d . . .
N2 N 0.37539(11) 0.66213(11) 0.70316(10) 0.0307(5) Uani 1 1 d . . .
N3 N 0.33353(9) 0.36099(9) 0.78887(9) 0.0169(4) Uani 1 1 d . . .
N4 N 0.2500 0.2500 0.87104(12) 0.0178(5) Uani 1 2 d S . .
O1 O 0.44825(10) 0.35244(9) 0.50079(9) 0.0365(4) Uani 1 1 d . . .
O2 O 0.40944(12) 0.47441(11) 0.44729(9) 0.0443(5) Uani 1 1 d . . .
O3 O 0.38859(12) 0.71207(10) 0.64545(10) 0.0498(5) Uani 1 1 d . . .
O4 O 0.36132(13) 0.68531(10) 0.77436(10) 0.0502(5) Uani 1 1 d . . .
O5 O 0.37844(8) 0.43282(8) 0.90941(7) 0.0229(4) Uani 1 1 d . . .
C1 C 0.38256(12) 0.39794(12) 0.65253(11) 0.0227(5) Uani 1 1 d . . .
H1 H 0.3867 0.3398 0.6404 0.027 Uiso 1 1 calc R . .
C2 C 0.39858(13) 0.45694(13) 0.59149(12) 0.0254(5) Uani 1 1 d . . .
C3 C 0.39605(13) 0.54519(13) 0.60393(12) 0.0268(5) Uani 1 1 d . . .
H3 H 0.4056 0.5845 0.5612 0.032 Uiso 1 1 calc R . .
C4 C 0.37802(12) 0.56951(12) 0.68543(11) 0.0233(5) Uani 1 1 d . . .
C5 C 0.36024(12) 0.51264(12) 0.74946(12) 0.0213(5) Uani 1 1 d . . .
H5 H 0.3486 0.5331 0.8029 0.026 Uiso 1 1 calc R . .
C6 C 0.35970(11) 0.42442(12) 0.73410(10) 0.0184(5) Uani 1 1 d . . .
C7 C 0.34061(11) 0.37188(11) 0.87193(10) 0.0177(5) Uani 1 1 d . . .
C8 C 0.29608(11) 0.30317(11) 0.91916(10) 0.0166(4) Uani 1 1 d . . .
C9 C 0.28049(11) 0.28403(12) 1.00429(11) 0.0183(5) Uani 1 1 d . . .
C10 C 0.31876(13) 0.32747(12) 1.07786(10) 0.0207(5) Uani 1 1 d . . .
C11 C 0.26815(13) 0.35583(13) 1.14468(11) 0.0255(5) Uani 1 1 d . . .
H11 H 0.2096 0.3448 1.1443 0.031 Uiso 1 1 calc R . .
C12 C 0.30390(15) 0.40014(13) 1.21155(12) 0.0313(6) Uani 1 1 d . . .
H12 H 0.2694 0.4181 1.2556 0.038 Uiso 1 1 calc R . .
C13 C 0.39059(16) 0.41746(14) 1.21263(12) 0.0354(6) Uani 1 1 d . . .
H13 H 0.4144 0.4480 1.2568 0.042 Uiso 1 1 calc R . .
C14 C 0.44262(15) 0.38897(14) 1.14701(12) 0.0338(6) Uani 1 1 d . . .
H14 H 0.5012 0.4000 1.1478 0.041 Uiso 1 1 calc R . .
C15 C 0.40650(13) 0.34391(12) 1.08033(12) 0.0245(5) Uani 1 1 d . . .
H15 H 0.4414 0.3247 1.0371 0.029 Uiso 1 1 calc R . .
O6A O 0.1986(6) 0.6343(6) 0.9494(3) 0.0426(8) Uani 0.15 1 d PDU A 1
H6A H 0.2430 0.6624 0.9486 0.064 Uiso 0.15 1 calc PR A 1
C16A C 0.1755(8) 0.6107(8) 0.8652(3) 0.0426(8) Uani 0.15 1 d PDU A 1
H16A H 0.1910 0.6560 0.8276 0.064 Uiso 0.15 1 calc PR A 1
H16B H 0.1148 0.6010 0.8622 0.064 Uiso 0.15 1 calc PR A 1
H16C H 0.2053 0.5592 0.8498 0.064 Uiso 0.15 1 calc PR A 1
O6B O 0.2331(2) 0.6437(3) 0.9406(2) 0.0426(8) Uani 0.35 1 d PDU B 2
H6B H 0.2506 0.5978 0.9589 0.064 Uiso 0.35 1 calc PRD B 2
C16B C 0.1731(3) 0.6283(4) 0.8752(3) 0.0426(8) Uani 0.35 1 d PDU B 2
H16D H 0.1281 0.6701 0.8779 0.064 Uiso 0.35 1 calc PR B 2
H16E H 0.1492 0.5720 0.8813 0.064 Uiso 0.35 1 calc PR B 2
H16F H 0.2016 0.6325 0.8221 0.064 Uiso 0.35 1 calc PR B 2
O7 O 0.45025(11) 0.60469(11) 1.08310(12) 0.0550(5) Uani 1 1 d U . .
H7 H 0.4991 0.5857 1.0797 0.083 Uiso 1 1 calc R . .
C17 C 0.44276(16) 0.65377(18) 1.15481(18) 0.0550(5) Uani 1 1 d U . .
H17A H 0.4575 0.6196 1.2026 0.083 Uiso 1 1 calc R . .
H17B H 0.3848 0.6737 1.1602 0.083 Uiso 1 1 calc R . .
H17C H 0.4808 0.7020 1.1513 0.083 Uiso 1 1 calc R . .
O8 O 0.366435(3) 0.713333(3) 0.968361(5) 0.0553(18) Uani 0.25 1 d PDU . .
H99 H 0.319860(3) 0.704008(4) 0.943640(5) 0.050 Uiso 0.25 1 d PD . .
H98 H 0.368789(6) 0.762369(3) 0.989921(5) 0.050 Uiso 0.25 1 d PD . .
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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
_geom_angle_publ_flag
N4 Ni1 N4 180.0 7_567 . ?
N4 Ni1 N3 106.01(4) 7_567 . ?
N4 Ni1 N3 73.99(4) . . ?
N4 Ni1 N3 73.99(4) 7_567 7_567 ?
N4 Ni1 N3 106.01(4) . 7_567 ?
N3 Ni1 N3 94.361(19) . 7_567 ?
N4 Ni1 N3 106.01(4) 7_567 2 ?
N4 Ni1 N3 73.99(4) . 2 ?
N3 Ni1 N3 147.99(7) . 2 ?
N3 Ni1 N3 94.361(19) 7_567 2 ?
N4 Ni1 N3 73.99(4) 7_567 8_657 ?
N4 Ni1 N3 106.01(4) . 8_657 ?
N3 Ni1 N3 94.361(19) . 8_657 ?
N3 Ni1 N3 147.99(7) 7_567 8_657 ?
N3 Ni1 N3 94.361(19) 2 8_657 ?
O5 K1 O3 168.91(5) . 4_465 ?
O5 K1 O1 89.95(4) . 8_657 ?
O3 K1 O1 80.29(5) 4_465 8_657 ?
O5 K1 C10 69.20(4) . . ?
O3 K1 C10 112.09(5) 4_465 . ?
O1 K1 C10 71.93(5) 8_657 . ?
O5 K1 C11 94.45(5) . . ?
O3 K1 C11 86.50(5) 4_465 . ?
O1 K1 C11 66.38(5) 8_657 . ?
C10 K1 C11 25.61(5) . . ?
O5 K1 C15 62.62(4) . . ?
O3 K1 C15 123.42(5) 4_465 . ?
O1 K1 C15 96.59(5) 8_657 . ?
C10 K1 C15 25.29(5) . . ?
C11 K1 C15 43.79(5) . . ?
O5 K1 C12 110.46(5) . . ?
O3 K1 C12 74.15(5) 4_465 . ?
O1 K1 C12 85.04(5) 8_657 . ?
C10 K1 C12 43.49(5) . . ?
C11 K1 C12 24.01(5) . . ?
C15 K1 C12 49.41(5) . . ?
O5 K1 C14 80.93(5) . . ?
O3 K1 C14 107.72(5) 4_465 . ?
O1 K1 C14 113.50(5) 8_657 . ?
C10 K1 C14 43.19(5) . . ?
C11 K1 C14 49.27(5) . . ?
C15 K1 C14 23.96(5) . . ?
C12 K1 C14 41.15(5) . . ?
O5 K1 C13 103.28(5) . . ?
O3 K1 C13 84.75(5) 4_465 . ?
O1 K1 C13 107.00(5) 8_657 . ?
C10 K1 C13 49.71(5) . . ?
C11 K1 C13 41.57(5) . . ?
C15 K1 C13 41.80(5) . . ?
C12 K1 C13 22.93(5) . . ?
C14 K1 C13 23.23(5) . . ?
O5 K1 C7 17.36(4) . . ?
O3 K1 C7 153.24(5) 4_465 . ?
O1 K1 C7 73.00(4) 8_657 . ?
C10 K1 C7 61.00(4) . . ?
C11 K1 C7 84.24(5) . . ?
C15 K1 C7 62.56(4) . . ?
C12 K1 C7 104.45(5) . . ?
C14 K1 C7 84.77(5) . . ?
C13 K1 C7 104.24(5) . . ?
O1 N1 O2 124.10(17) . . ?
O1 N1 C2 117.57(16) . . ?
O2 N1 C2 118.31(17) . . ?
O4 N2 O3 123.19(17) . . ?
O4 N2 C4 118.52(16) . . ?
O3 N2 C4 118.29(16) . . ?
C7 N3 C6 120.75(15) . . ?
C7 N3 Ni1 114.66(11) . . ?
C6 N3 Ni1 123.05(11) . . ?
C8 N4 C8 109.9(2) . 2 ?
C8 N4 Ni1 125.04(10) . . ?
C8 N4 Ni1 125.04(10) 2 . ?
N1 O1 K1 172.67(12) . 7_567 ?
N2 O3 K1 158.83(15) . 3_654 ?
C7 O5 K1 124.14(11) . . ?
C2 C1 C6 120.61(18) . . ?
C1 C2 C3 124.03(18) . . ?
C1 C2 N1 118.17(17) . . ?
C3 C2 N1 117.80(17) . . ?
C4 C3 C2 114.26(17) . . ?
C5 C4 C3 124.15(18) . . ?
C5 C4 N2 118.75(16) . . ?
C3 C4 N2 117.07(16) . . ?
C4 C5 C6 120.17(17) . . ?
N3 C6 C5 126.50(16) . . ?
N3 C6 C1 116.73(16) . . ?
C5 C6 C1 116.62(16) . . ?
O5 C7 N3 126.85(16) . . ?
O5 C7 C8 121.21(15) . . ?
N3 C7 C8 111.93(15) . . ?
N3 C7 K1 143.29(12) . . ?
C8 C7 K1 92.35(10) . . ?
N4 C8 C9 109.25(16) . . ?
N4 C8 C7 113.93(15) . . ?
C9 C8 C7 136.28(16) . . ?
C8 C9 C9 105.77(10) . 2 ?
C8 C9 C10 126.71(16) . . ?
C9 C9 C10 127.50(10) 2 . ?
C15 C10 C11 118.30(17) . . ?
C15 C10 C9 120.13(16) . . ?
C11 C10 C9 121.53(17) . . ?
C15 C10 K1 82.36(11) . . ?
C11 C10 K1 80.84(11) . . ?
C9 C10 K1 104.50(11) . . ?
C12 C11 C10 121.21(19) . . ?
C12 C11 K1 86.57(12) . . ?
C10 C11 K1 73.56(11) . . ?
C13 C12 C11 120.02(19) . . ?
C13 C12 K1 82.61(12) . . ?
C11 C12 K1 69.42(11) . . ?
C12 C13 C14 119.82(19) . . ?
C12 C13 K1 74.46(12) . . ?
C14 C13 K1 75.12(12) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 K1 70.08(12) . . ?
C13 C14 K1 81.65(13) . . ?
C10 C15 C14 120.73(18) . . ?
C10 C15 K1 72.35(11) . . ?
C14 C15 K1 85.96(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N4 1.9363(19) 7_567 ?
Ni1 N4 1.9363(19) . ?
Ni1 N3 2.2547(15) . ?
Ni1 N3 2.2547(15) 7_567 ?
Ni1 N3 2.2547(15) 2 ?
Ni1 N3 2.2547(14) 8_657 ?
K1 O5 2.6492(13) . ?
K1 O3 2.7389(17) 4_465 ?
K1 O1 2.8448(15) 8_657 ?
K1 C10 3.1081(19) . ?
K1 C11 3.199(2) . ?
K1 C15 3.233(2) . ?
K1 C12 3.411(2) . ?
K1 C14 3.430(2) . ?
K1 C13 3.511(2) . ?
K1 C7 3.5220(18) . ?
N1 O1 1.227(2) . ?
N1 O2 1.232(2) . ?
N1 C2 1.476(2) . ?
N2 O4 1.215(2) . ?
N2 O3 1.226(2) . ?
N2 C4 1.473(3) . ?
N3 C7 1.344(2) . ?
N3 C6 1.383(2) . ?
N4 C8 1.341(2) . ?
N4 C8 1.341(2) 2 ?
O1 K1 2.8448(15) 7_567 ?
O3 K1 2.7389(17) 3_654 ?
O5 C7 1.269(2) . ?
C1 C2 1.365(3) . ?
C1 C6 1.414(2) . ?
C2 C3 1.392(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.398(3) . ?
C7 C8 1.484(2) . ?
C8 C9 1.415(2) . ?
C9 C9 1.426(4) 2 ?
C9 C10 1.484(2) . ?
C10 C15 1.393(3) . ?
C10 C11 1.401(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.400(3) . ?
C14 C15 1.396(3) . ?
O6A C16A 1.442(7) . ?
O6B C16B 1.425(5) . ?
O7 C17 1.384(3) . ?
