#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:19:21 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179685 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/07/7000728.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_7000728
loop_
_publ_author_name
'Lü, Jian'
'Gao, Shui-Ying'
'Lin, Jing-Xiang'
'Shi, Lin-Xi'
'Cao, Rong'
'Batten, Stuart R.'
_publ_section_title
;
 Systematic investigation on the coordination chemistry of a sulfonated
 monoazo dye: Ligand-dominated d- and f-block derivatives
;
_journal_issue                   11
_journal_name_full               'Dalton Transactions'
_journal_page_first              1944
_journal_page_last               1953
_journal_paper_doi               10.1039/b814774d
_journal_year                    2009
_chemical_formula_sum            'C24 H25 N6 Na O8 S2'
_chemical_formula_weight         612.61
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.300(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   33.554(15)
_cell_length_b                   11.965(4)
_cell_length_c                   14.577(5)
_cell_measurement_reflns_used    5966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.34
_cell_volume                     5291(3)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Mercury70 (2x2 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19967
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trunk
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         5966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                5126
_reflns_number_total             5966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B814774d.txt
_cod_data_source_block           compd2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      C2/c
_cod_database_code               7000728
loop_
_symmetry_equiv_pos_as_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_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
S1 S 0.188446(13) 0.72746(3) 0.00094(3) 0.02509(14) Uani 1 1 d . . .
S2 S 0.683380(13) 0.28657(3) 0.53387(3) 0.02608(14) Uani 1 1 d . . .
O6 O 0.69433(4) 0.28569(10) 0.44805(11) 0.0347(3) Uani 1 1 d . . .
O3 O 0.19005(4) 0.84901(10) 0.00182(10) 0.0335(3) Uani 1 1 d . . .
O2 O 0.21454(4) 0.67952(11) 0.10030(10) 0.0366(3) Uani 1 1 d . . .
O1 O 0.19883(4) 0.68028(10) -0.07857(10) 0.0340(3) Uani 1 1 d . . .
C13 C 0.62704(5) 0.32351(13) 0.48588(13) 0.0251(3) Uani 1 1 d . . .
N6 N 0.49297(5) 0.40346(12) 0.36943(13) 0.0362(4) Uani 1 1 d . . .
O5 O 0.70778(4) 0.37165(10) 0.60840(10) 0.0351(3) Uani 1 1 d . . .
C22 C 0.35016(5) 0.58485(14) 0.24471(13) 0.0281(4) Uani 1 1 d . . .
O4 O 0.68698(4) 0.17646(10) 0.57842(12) 0.0440(4) Uani 1 1 d . . .
C2 C 0.10786(6) 0.75651(14) 0.00318(17) 0.0351(4) Uani 1 1 d . . .
C8 C -0.08244(6) 0.54536(15) -0.13500(15) 0.0347(4) Uani 1 1 d . . .
C18 C 0.59562(6) 0.24117(14) 0.46646(16) 0.0325(4) Uani 1 1 d . . .
C7 C -0.05352(5) 0.48025(13) -0.15795(14) 0.0280(3) Uani 1 1 d . . .
N1 N -0.18753(5) 0.39708(14) -0.27431(15) 0.0384(4) Uani 1 1 d . . .
C16 C 0.53929(5) 0.38144(14) 0.40822(14) 0.0309(4) Uani 1 1 d . . .
C11 C -0.11313(6) 0.35533(14) -0.25341(15) 0.0311(4) Uani 1 1 d . . .
N5 N 0.48356(5) 0.50416(13) 0.36129(14) 0.0376(4) Uani 1 1 d . . .
N4 N 0.30345(5) 0.61580(14) 0.20326(13) 0.0313(3) Uani 1 1 d . . .
N2 N -0.00874(5) 0.50683(12) -0.13028(12) 0.0320(3) Uani 1 1 d . . .
N3 N 0.00258(5) 0.60324(12) -0.09496(13) 0.0335(3) Uani 1 1 d . . .
C1 C 0.13308(5) 0.69038(13) -0.02946(13) 0.0260(3) Uani 1 1 d . . .
C15 C 0.57081(6) 0.46316(14) 0.42536(17) 0.0376(4) Uani 1 1 d . . .
C6 C 0.11601(6) 0.59257(15) -0.08231(16) 0.0372(4) Uani 1 1 d . . .
C24 C 0.40548(6) 0.44420(15) 0.30216(16) 0.0379(4) Uani 1 1 d . . .
C19 C 0.43746(6) 0.52642(14) 0.32229(15) 0.0323(4) Uani 1 1 d . . .
C10 C -0.14219(5) 0.42103(14) -0.23221(14) 0.0293(4) Uani 1 1 d . . .
C5 C 0.07332(6) 0.56163(15) -0.10338(16) 0.0373(4) Uani 1 1 d . . .
C12 C -0.06884(6) 0.38377(13) -0.21525(15) 0.0310(4) Uani 1 1 d . . .
C14 C 0.61489(6) 0.43495(14) 0.46419(16) 0.0359(4) Uani 1 1 d . . .
C17 C 0.55144(6) 0.27040(15) 0.42748(17) 0.0361(4) Uani 1 1 d . . .
C23 C 0.36163(6) 0.47393(15) 0.26314(17) 0.0370(4) Uani 1 1 d . . .
C4 C 0.04749(5) 0.62859(13) -0.07268(14) 0.0288(4) Uani 1 1 d . . .
C3 C 0.06471(6) 0.72644(14) -0.01950(17) 0.0375(5) Uani 1 1 d . . .
C20 C 0.42548(6) 0.63755(15) 0.30460(18) 0.0416(5) Uani 1 1 d . . .
C9 C -0.12617(6) 0.51555(15) -0.17044(16) 0.0355(4) Uani 1 1 d . . .
C21 C 0.38124(6) 0.66716(15) 0.26452(17) 0.0392(4) Uani 1 1 d . . .
Na2 Na 0.25390(2) 0.96306(6) 0.09801(6) 0.03406(19) Uani 1 1 d . . .
O1W O 0.74623(5) 0.45867(11) 0.44401(11) 0.0364(3) Uani 1 1 d . . .
O2W O 0.24350(8) 0.87622(17) 0.23034(14) 0.0604(5) Uani 1 1 d . . .
H11A H -0.1242(7) 0.2884(16) -0.2960(17) 0.033(5) Uiso 1 1 d . . .
H18A H 0.6042(7) 0.1655(18) 0.4799(17) 0.041(6) Uiso 1 1 d . . .
H12A H -0.0497(7) 0.3394(17) -0.2344(17) 0.041(5) Uiso 1 1 d . . .
H1C H 0.2949(7) 0.6222(17) 0.2556(19) 0.043(6) Uiso 1 1 d . . .
H3A H 0.0490(9) 0.7685(19) 0.006(2) 0.057(7) Uiso 1 1 d . . .
H17A H 0.5288(9) 0.216(2) 0.413(2) 0.064(8) Uiso 1 1 d . . .
H6A H 0.1320(8) 0.5464(18) -0.1101(19) 0.053(6) Uiso 1 1 d . . .
H14A H 0.6370(9) 0.492(2) 0.483(2) 0.063(7) Uiso 1 1 d . . .
H20A H 0.4456(8) 0.6975(18) 0.3189(19) 0.049(6) Uiso 1 1 d . . .
H9A H -0.1457(8) 0.5617(19) -0.1538(19) 0.055(7) Uiso 1 1 d . . .
H24A H 0.4135(7) 0.3697(18) 0.3164(17) 0.043(6) Uiso 1 1 d . . .
H8A H -0.0726(6) 0.6103(16) -0.0965(16) 0.031(5) Uiso 1 1 d . . .
H23A H 0.3397(8) 0.4221(19) 0.2501(19) 0.054(7) Uiso 1 1 d . . .
H15A H 0.5619(8) 0.5386(19) 0.409(2) 0.056(7) Uiso 1 1 d . . .
H1A H -0.1964(8) 0.399(2) -0.226(2) 0.055(7) Uiso 1 1 d . . .
H2A H 0.1204(7) 0.8233(18) 0.0437(18) 0.045(6) Uiso 1 1 d . . .
H21A H 0.3732(8) 0.7438(18) 0.247(2) 0.049(6) Uiso 1 1 d . . .
H1E H 0.7309(8) 0.399(2) 0.4371(17) 0.043(6) Uiso 1 1 d . . .
H5A H 0.0594(9) 0.496(2) -0.146(2) 0.063(7) Uiso 1 1 d . . .
H1G H -0.1940(8) 0.334(2) -0.311(2) 0.046(6) Uiso 1 1 d . . .
H1D H 0.7691(9) 0.433(2) 0.445(2) 0.055(7) Uiso 1 1 d . . .
H1I H 0.2673(9) 0.849(2) 0.261(2) 0.051(8) Uiso 1 1 d . . .
H1F H 0.2842(9) 0.563(2) 0.155(2) 0.073(8) Uiso 1 1 d . . .
H1X H 0.2998(8) 0.680(2) 0.172(2) 0.045(6) Uiso 1 1 d . . .
H1H H 0.2348(13) 0.807(3) 0.207(3) 0.098(12) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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
O2 S1 O3 112.43(8) . . ?
O2 S1 O1 113.11(8) . . ?
O3 S1 O1 111.91(7) . . ?
O2 S1 C1 105.74(8) . . ?
O3 S1 C1 106.46(7) . . ?
O1 S1 C1 106.57(8) . . ?
O6 S2 O4 112.15(8) . . ?
O6 S2 O5 112.34(8) . . ?
O4 S2 O5 112.81(9) . . ?
O6 S2 C13 106.46(8) . . ?
O4 S2 C13 105.93(8) . . ?
O5 S2 C13 106.57(7) . . ?
S1 O3 Na2 126.11(7) . . ?
S1 O1 Na2 138.94(8) . 7_565 ?
C18 C13 C14 120.90(15) . . ?
C18 C13 S2 119.74(13) . . ?
C14 C13 S2 119.30(12) . . ?
N5 N6 C16 113.93(14) . . ?
S2 O5 Na2 131.12(8) . 8_566 ?
C21 C22 C23 121.81(16) . . ?
C21 C22 N4 119.20(15) . . ?
C23 C22 N4 118.99(15) . . ?
C1 C2 C3 119.94(16) . . ?
C9 C8 C7 120.32(17) . . ?
C13 C18 C17 119.52(16) . . ?
C12 C7 C8 119.55(15) . . ?
C12 C7 N2 115.67(14) . . ?
C8 C7 N2 124.74(15) . . ?
C10 N1 Na2 121.22(11) . 8_465 ?
C15 C16 C17 120.42(16) . . ?
C15 C16 N6 123.94(15) . . ?
C17 C16 N6 115.64(15) . . ?
C12 C11 C10 120.40(16) . . ?
N6 N5 C19 114.10(15) . . ?
N3 N2 C7 114.96(14) . . ?
N2 N3 C4 113.13(14) . . ?
C2 C1 C6 120.47(15) . . ?
C2 C1 S1 120.06(13) . . ?
C6 C1 S1 119.42(12) . . ?
C14 C15 C16 120.26(16) . . ?
C5 C6 C1 119.59(16) . . ?
C23 C24 C19 119.71(17) . . ?
C20 C19 C24 120.30(16) . . ?
C20 C19 N5 115.70(15) . . ?
C24 C19 N5 124.00(15) . . ?
C11 C10 C9 119.18(15) . . ?
C11 C10 N1 121.35(17) . . ?
C9 C10 N1 119.43(16) . . ?
C6 C5 C4 120.34(17) . . ?
C11 C12 C7 120.17(16) . . ?
C15 C14 C13 119.09(16) . . ?
C16 C17 C18 119.76(16) . . ?
C22 C23 C24 119.32(17) . . ?
C5 C4 C3 119.96(15) . . ?
C5 C4 N3 123.13(15) . . ?
C3 C4 N3 116.90(14) . . ?
C2 C3 C4 119.68(16) . . ?
C19 C20 C21 119.84(17) . . ?
C8 C9 C10 120.28(16) . . ?
C22 C21 C20 119.01(17) . . ?
O1W Na2 O2W 166.27(8) 8_465 . ?
O1W Na2 O3 87.86(6) 8_465 . ?
O2W Na2 O3 79.67(7) . . ?
O1W Na2 O1 88.87(5) 8_465 7_565 ?
O2W Na2 O1 96.72(7) . 7_565 ?
O3 Na2 O1 89.70(5) . 7_565 ?
O1W Na2 O5 85.76(5) 8_465 8_465 ?
O2W Na2 O5 89.28(7) . 8_465 ?
O3 Na2 O5 93.57(5) . 8_465 ?
O1 Na2 O5 173.60(5) 7_565 8_465 ?
O1W Na2 N1 99.53(7) 8_465 8_566 ?
O2W Na2 N1 91.63(8) . 8_566 ?
O3 Na2 N1 166.47(6) . 8_566 ?
O1 Na2 N1 101.68(6) 7_565 8_566 ?
O5 Na2 N1 75.84(5) 8_465 8_566 ?
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
S1 O2 1.4525(14) . ?
S1 O3 1.4552(13) . ?
S1 O1 1.4590(13) . ?
S1 C1 1.7722(18) . ?
S2 O6 1.4468(15) . ?
S2 O4 1.4508(13) . ?
S2 O5 1.4583(13) . ?
S2 C13 1.7687(17) . ?
O3 Na2 2.4186(15) . ?
O1 Na2 2.4334(14) 7_565 ?
C13 C18 1.381(2) . ?
C13 C14 1.391(2) . ?
N6 N5 1.238(2) . ?
N6 C16 1.433(2) . ?
O5 Na2 2.5552(15) 8_566 ?
C22 C21 1.372(3) . ?
C22 C23 1.376(2) . ?
C22 N4 1.466(2) . ?
C2 C1 1.383(2) . ?
C2 C3 1.388(2) . ?
C8 C9 1.378(2) . ?
C8 C7 1.392(2) . ?
C18 C17 1.387(2) . ?
C7 C12 1.388(2) . ?
C7 N2 1.415(2) . ?
N1 C10 1.405(2) . ?
N1 Na2 2.6460(19) 8_465 ?
C16 C15 1.383(2) . ?
C16 C17 1.383(2) . ?
C11 C12 1.388(2) . ?
C11 C10 1.386(2) . ?
N5 C19 1.427(2) . ?
N2 N3 1.254(2) . ?
N3 C4 1.432(2) . ?
C1 C6 1.383(2) . ?
C15 C14 1.381(2) . ?
C6 C5 1.381(3) . ?
C24 C23 1.378(3) . ?
C24 C19 1.391(2) . ?
C19 C20 1.381(2) . ?
C10 C9 1.402(3) . ?
C5 C4 1.388(2) . ?
C4 C3 1.387(2) . ?
C20 C21 1.389(3) . ?
Na2 O1W 2.3428(17) 8_465 ?
Na2 O2W 2.345(2) . ?
Na2 O1 2.4334(14) 7_565 ?
Na2 O5 2.5552(15) 8_465 ?
Na2 N1 2.6460(19) 8_566 ?
O1W Na2 2.3428(17) 8_566 ?
