#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201496.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_2201496
loop_
_publ_author_name
'Deschamps, Jeffrey R.'
'Hartshorn, Christopher M.'
'Chang, Eddie L.'
_publ_section_title
;Bis[μ-bis(4-nitrophenyl)
 phosphato-κ²O:O]bis[(4,4'-dimethyl-2,2'-bipyridine)nitratocopper(II)]
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m606
_journal_page_last               m608
_journal_paper_doi               10.1107/S1600536802017671
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac
'[Cu2 (C12 H8 N2 O8 P)2 (C12 H12 N2)2 (N O3)2]'
_chemical_formula_moiety         'C48 H40 Cu2 N10 O22 P2'
_chemical_formula_sum            'C48 H40 Cu2 N10 O22 P2'
_chemical_formula_weight         1297.92
_chemical_name_systematic
;
Bis[μ-bis(4-nitrophenyl)
phosphate-κ²O:O]bis[(4,4'-dimethyl-2,2'-bipyridine)nitratocopper(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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                96.159(5)
_cell_angle_beta                 96.421(7)
_cell_angle_gamma                113.044(4)
_cell_formula_units_Z            1
_cell_length_a                   10.9572(5)
_cell_length_b                   11.5226(6)
_cell_length_c                   12.0697(11)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.72
_cell_volume                     1374.33(17)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4685
_diffrn_reflns_theta_full        58.09
_diffrn_reflns_theta_max         58.09
_diffrn_reflns_theta_min         3.74
_diffrn_standards_decay_%        'random variation of 2%'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_T_max  0.8560
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Bruker, 1997)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.255
_refine_ls_extinction_coef       0.00044(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0359
_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)+(0.0358P)²+1.4102P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3333
_reflns_number_total             3829
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6003.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.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1374.32(16)
_cod_database_code               2201496
_cod_database_fobs_code          2201496
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.01873(4) 0.21729(4) 0.06005(3) 0.03153(16) Uani d . 1 . . Cu
N1 0.0010(2) 0.2724(2) -0.0882(2) 0.0328(6) Uani d . 1 . . N
C2 -0.0677(3) 0.1937(3) -0.1851(3) 0.0431(8) Uani d . 1 . . C
H2A -0.1149 0.1051 -0.1839 0.052 Uiso calc R 1 . . H
C3 -0.0716(4) 0.2380(4) -0.2862(3) 0.0500(9) Uani d . 1 . . C
H3A -0.1208 0.1798 -0.3535 0.060 Uiso calc R 1 . . H
C4 -0.0047(4) 0.3662(3) -0.2905(3) 0.0460(9) Uani d . 1 . . C
C4A -0.0091(5) 0.4185(4) -0.3988(3) 0.0684(12) Uani d . 1 . . C
H4AA -0.0660 0.3489 -0.4604 0.103 Uiso calc R 1 . . H
H4AB 0.0822 0.4577 -0.4160 0.103 Uiso calc R 1 . . H
H4AC -0.0464 0.4830 -0.3908 0.103 Uiso calc R 1 . . H
C5 0.0690(3) 0.4459(3) -0.1906(3) 0.0420(8) Uani d . 1 . . C
H5A 0.1177 0.5347 -0.1903 0.050 Uiso calc R 1 . . H
C6 0.0723(3) 0.3969(3) -0.0907(2) 0.0318(7) Uani d . 1 . . C
C7 0.1534(3) 0.4723(3) 0.0191(2) 0.0323(7) Uani d . 1 . . C
C8 0.2300(3) 0.6025(3) 0.0381(3) 0.0398(8) Uani d . 1 . . C
H8A 0.2316 0.6498 -0.0220 0.048 Uiso calc R 1 . . H
C9 0.3043(3) 0.6651(3) 0.1436(3) 0.0397(8) Uani d . 1 . . C
C9A 0.3850(4) 0.8074(3) 0.1657(3) 0.0549(10) Uani d . 1 . . C
H9AA 0.4323 0.8341 0.2441 0.082 Uiso calc R 1 . . H
H9AB 0.3247 0.8506 0.1532 0.082 Uiso calc R 1 . . H
H9AC 0.4507 0.8303 0.1143 0.082 Uiso calc R 1 . . H
C10 0.3006(3) 0.5912(3) 0.2270(3) 0.0461(8) Uani d . 1 . . C
H10A 0.3516 0.6301 0.3003 0.055 Uiso calc R 1 . . H
C11 0.2236(3) 0.4620(3) 0.2046(3) 0.0432(8) Uani d . 1 . . C
H11A 0.2233 0.4130 0.2631 0.052 Uiso calc R 1 . . H
N12 0.1483(3) 0.4019(2) 0.1026(2) 0.0337(6) Uani d . 1 . . N
P1 0.22037(8) 0.05933(7) -0.03628(6) 0.0316(2) Uani d . 1 . . P
O1 0.2369(2) 0.05876(19) -0.16615(17) 0.0389(5) Uani d . 1 . . O
C13 0.2592(3) 0.1605(3) -0.2253(3) 0.0367(7) Uani d . 1 . . C
C14 0.2110(4) 0.1279(4) -0.3396(3) 0.0524(9) Uani d . 1 . . C
H14A 0.1611 0.0407 -0.3728 0.063 Uiso calc R 1 . . H
C15 0.2355(4) 0.2224(4) -0.4058(3) 0.0641(11) Uani d . 1 . . C
H15A 0.2036 0.2013 -0.4849 0.077 Uiso calc R 1 . . H
C16 0.3063(4) 0.3466(4) -0.3558(3) 0.0550(10) Uani d . 1 . . C
N16 0.3308(5) 0.4477(5) -0.4273(4) 0.0913(13) Uani d . 1 . . N
O7 0.3757(7) 0.5550(4) -0.3818(4) 0.170(3) Uani d . 1 . . O
O8 0.3009(5) 0.4164(4) -0.5281(3) 0.1309(17) Uani d . 1 . . O
C17 0.3520(4) 0.3802(4) -0.2422(4) 0.0604(11) Uani d . 1 . . C
H17A 0.3997 0.4677 -0.2096 0.073 Uiso calc R 1 . . H
C18 0.3290(4) 0.2867(3) -0.1749(3) 0.0513(9) Uani d . 1 . . C
H18A 0.3604 0.3088 -0.0957 0.062 Uiso calc R 1 . . H
O2 0.1566(2) 0.1440(2) 0.00081(19) 0.0475(6) Uani d . 1 . . O
O3 0.3772(2) 0.1192(2) 0.01844(17) 0.0394(5) Uani d . 1 . . O
C19 0.4243(3) 0.1295(3) 0.1326(3) 0.0353(7) Uani d . 1 . . C
C20 0.5500(3) 0.1308(3) 0.1590(3) 0.0457(8) Uani d . 1 . . C
H20A 0.6007 0.1262 0.1011 0.055 Uiso calc R 1 . . H
C21 0.6022(4) 0.1388(4) 0.2709(3) 0.0588(10) Uani d . 1 . . C
H21A 0.6886 0.1389 0.2912 0.071 Uiso calc R 1 . . H
C22 0.5259(4) 0.1467(4) 0.3515(3) 0.0588(11) Uani d . 1 . . C
N22 0.5809(5) 0.1548(4) 0.4712(4) 0.0962(15) Uani d . 1 . . N
O5 0.5160(5) 0.1678(5) 0.5427(3) 0.1358(18) Uani d . 1 . . O
O6 0.6864(5) 0.1492(6) 0.4928(4) 0.162(2) Uani d . 1 . . O
C23 0.4017(4) 0.1469(4) 0.3269(3) 0.0588(10) Uani d . 1 . . C
H23A 0.3518 0.1518 0.3854 0.071 Uiso calc R 1 . . H
C24 0.3493(4) 0.1397(4) 0.2154(3) 0.0497(9) Uani d . 1 . . C
H24A 0.2637 0.1416 0.1960 0.060 Uiso calc R 1 . . H
O4 0.1626(2) -0.0768(2) -0.02068(18) 0.0415(5) Uani d . 1 . . O
N25 -0.0143(4) 0.2094(3) 0.2799(2) 0.0580(9) Uani d . 1 . . N
O9 0.0513(2) 0.1724(2) 0.20940(18) 0.0436(6) Uani d . 1 . . O
O10 -0.0770(3) 0.2699(3) 0.2473(3) 0.0767(9) Uani d . 1 . . O
O11 -0.0074(4) 0.1804(3) 0.3743(2) 0.1007(13) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
O9 Cu1 O4 . 2 92.94(9) y
O9 Cu1 O2 . . 90.56(9) y
O9 Cu1 N1 . . 175.44(10) y
O9 Cu1 N12 . . 95.33(10) y
O4 Cu1 O2 2 . 106.98(9) y
O4 Cu1 N1 2 . 91.58(9) y
O4 Cu1 N12 2 . 153.94(10) y
N1 Cu1 O2 . . 87.52(9) y
N1 Cu1 N12 . . 80.83(10) y
N12 Cu1 O2 . . 97.62(10) y
C2 N1 C6 . . 119.0(3) ?
C2 N1 Cu1 . . 124.8(2) ?
C6 N1 Cu1 . . 115.95(19) ?
N1 C2 C3 . . 121.8(3) ?
N1 C2 H2A . . 119.1 ?
C3 C2 H2A . . 119.1 ?
C2 C3 C4 . . 120.4(3) ?
C2 C3 H3A . . 119.8 ?
C4 C3 H3A . . 119.8 ?
C3 C4 C5 . . 117.3(3) ?
C3 C4 C4A . . 122.0(3) ?
C5 C4 C4A . . 120.7(3) ?
C4 C4A H4AA . . 109.5 ?
C4 C4A H4AB . . 109.5 ?
H4AA C4A H4AB . . 109.5 ?
C4 C4A H4AC . . 109.5 ?
H4AA C4A H4AC . . 109.5 ?
H4AB C4A H4AC . . 109.5 ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
N1 C6 C5 . . 121.0(3) ?
N1 C6 C7 . . 114.4(2) ?
C5 C6 C7 . . 124.6(3) ?
N12 C7 C8 . . 121.3(3) ?
N12 C7 C6 . . 114.0(3) ?
C8 C7 C6 . . 124.8(3) ?
C7 C8 C9 . . 120.8(3) ?
C7 C8 H8A . . 119.6 ?
C9 C8 H8A . . 119.6 ?
C10 C9 C8 . . 117.1(3) ?
C10 C9 C9A . . 121.8(3) ?
C8 C9 C9A . . 121.1(3) ?
C9 C9A H9AA . . 109.5 ?
C9 C9A H9AB . . 109.5 ?
H9AA C9A H9AB . . 109.5 ?
C9 C9A H9AC . . 109.5 ?
H9AA C9A H9AC . . 109.5 ?
H9AB C9A H9AC . . 109.5 ?
C11 C10 C9 . . 120.3(3) ?
C11 C10 H10A . . 119.9 ?
C9 C10 H10A . . 119.9 ?
N12 C11 C10 . . 122.5(3) ?
N12 C11 H11A . . 118.8 ?
C10 C11 H11A . . 118.8 ?
C11 N12 C7 . . 118.0(3) ?
C11 N12 Cu1 . . 127.3(2) ?
C7 N12 Cu1 . . 114.6(2) ?
O2 P1 O4 . . 119.96(14) ?
O2 P1 O1 . . 111.88(12) ?
O4 P1 O1 . . 106.35(12) ?
O2 P1 O3 . . 110.80(13) ?
O4 P1 O3 . . 107.31(12) ?
O1 P1 O3 . . 98.25(11) ?
C13 O1 P1 . . 126.6(2) ?
C14 C13 C18 . . 121.2(3) ?
C14 C13 O1 . . 115.8(3) ?
C18 C13 O1 . . 123.0(3) ?
C13 C14 C15 . . 119.6(4) ?
C13 C14 H14A . . 120.2 ?
C15 C14 H14A . . 120.2 ?
C16 C15 C14 . . 118.9(4) ?
C16 C15 H15A . . 120.6 ?
C14 C15 H15A . . 120.6 ?
C15 C16 C17 . . 121.9(3) ?
C15 C16 N16 . . 118.6(4) ?
C17 C16 N16 . . 119.5(4) ?
O7 N16 O8 . . 123.3(4) ?
O7 N16 C16 . . 118.0(5) ?
O8 N16 C16 . . 118.6(5) ?
C16 C17 C18 . . 119.9(4) ?
C16 C17 H17A . . 120.0 ?
C18 C17 H17A . . 120.0 ?
C17 C18 C13 . . 118.4(3) ?
C17 C18 H18A . . 120.8 ?
C13 C18 H18A . . 120.8 ?
P1 O2 Cu1 . . 163.66(16) ?
C19 O3 P1 . . 123.85(19) ?
C20 C19 C24 . . 121.7(3) ?
C20 C19 O3 . . 116.4(3) ?
C24 C19 O3 . . 121.9(3) ?
C19 C20 C21 . . 119.4(3) ?
C19 C20 H20A . . 120.3 ?
C21 C20 H20A . . 120.3 ?
C22 C21 C20 . . 118.1(3) ?
C22 C21 H21A . . 120.9 ?
C20 C21 H21A . . 120.9 ?
C23 C22 C21 . . 123.2(3) ?
C23 C22 N22 . . 118.4(4) ?
C21 C22 N22 . . 118.4(4) ?
O6 N22 O5 . . 123.0(5) ?
O6 N22 C22 . . 118.8(5) ?
O5 N22 C22 . . 118.2(5) ?
C22 C23 C24 . . 119.0(4) ?
C22 C23 H23A . . 120.5 ?
C24 C23 H23A . . 120.5 ?
C23 C24 C19 . . 118.5(3) ?
C23 C24 H24A . . 120.7 ?
C19 C24 H24A . . 120.7 ?
P1 O4 Cu1 . 2 134.24(13) ?
O10 N25 O11 . . 124.8(4) ?
O10 N25 O9 . . 118.2(3) ?
O11 N25 O9 . . 117.1(4) ?
N25 O9 Cu1 . . 111.2(2) ?
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
Cu1 O9 . 1.961(2) y
Cu1 O4 2 1.975(2) y
Cu1 N1 . 1.976(2) y
Cu1 N12 . 2.011(3) y
Cu1 O2 . 2.149(2) y
N1 C2 . 1.341(4) ?
N1 C6 . 1.344(4) ?
C2 C3 . 1.374(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.378(5) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.384(5) ?
C4 C4A . 1.501(4) ?
C4A H4AA . 0.9800 ?
C4A H4AB . 0.9800 ?
C4A H4AC . 0.9800 ?
C5 C6 . 1.387(4) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.479(4) ?
C7 N12 . 1.353(4) ?
C7 C8 . 1.380(4) ?
C8 C9 . 1.385(5) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.380(5) ?
C9 C9A . 1.503(4) ?
C9A H9AA . 0.9800 ?
C9A H9AB . 0.9800 ?
C9A H9AC . 0.9800 ?
C10 C11 . 1.371(5) ?
C10 H10A . 0.9500 ?
C11 N12 . 1.348(4) ?
C11 H11A . 0.9500 ?
P1 O2 . 1.466(2) y
P1 O4 . 1.486(2) y
P1 O1 . 1.598(2) y
P1 O3 . 1.608(2) y
O1 C13 . 1.392(4) ?
C13 C14 . 1.376(5) ?
C13 C18 . 1.381(5) ?
C14 C15 . 1.379(5) ?
C14 H14A . 0.9500 ?
C15 C16 . 1.362(6) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.364(5) ?
C16 N16 . 1.482(5) ?
N16 O7 . 1.178(6) ?
N16 O8 . 1.201(5) ?
C17 C18 . 1.380(5) ?
C17 H17A . 0.9500 ?
C18 H18A . 0.9500 ?
O3 C19 . 1.391(4) ?
C19 C20 . 1.372(4) ?
C19 C24 . 1.387(5) ?
C20 C21 . 1.386(5) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.370(6) ?
C21 H21A . 0.9500 ?
C22 C23 . 1.360(6) ?
C22 N22 . 1.480(5) ?
N22 O6 . 1.185(6) ?
N22 O5 . 1.211(6) ?
C23 C24 . 1.384(5) ?
C23 H23A . 0.9500 ?
C24 H24A . 0.9500 ?
O4 Cu1 2 1.975(2) ?
N25 O10 . 1.220(4) ?
N25 O11 . 1.224(4) ?
N25 O9 . 1.311(4) ?
