#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:30:08 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179793 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/89/7008973.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_7008973
loop_
_publ_author_name
'Grove, Hilde'
'Sletten, Jorunn'
'Julve, Miguel'
'Lloret, Francesc'
_publ_section_title
;
 Syntheses, crystal structures and magnetic properties of dinuclear
 copper(II) complexes with
 pyrazino[2,3-f  ][4,7]phenanthroline (pap) as bridging
 ligand
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              515
_journal_paper_doi               10.1039/a907658a
_journal_year                    2000
_chemical_compound_source        'synthesized by H. Grove'
_chemical_formula_structural     'C14 H14 Cu2 N8 O15'
_chemical_formula_sum            'C14 H14 Cu2 N8 O15'
_chemical_formula_weight         661.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   'geom if bonded to C, difmap if bonded to O'
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.149(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7332(3)
_cell_length_b                   9.0065(3)
_cell_length_c                   27.6888(4)
_cell_measurement_temperature    173(2)
_cell_volume                     2155.89(11)
_computing_cell_refinement       'SAINT, version 4.0'
_computing_data_collection       'SMART, version 4.0'
_computing_data_reduction        'SAINT, version 4.0'
_computing_molecular_graphics    'XP, version 4.3, 1992'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       '2K SMART CCD'
_diffrn_measurement_method       ω
_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  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            35247
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_type   'empirical, SADABS'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    2.038
_exptl_crystal_description       plates
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.016
_refine_ls_goodness_of_fit_obs   1.054
_refine_ls_hydrogen_treatment
'riding model if bonded to C, isotropic ref if bonded to O'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_restrained_S_obs      1.054
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_obs          0.0347
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+1.8339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0805
_refine_ls_wR_factor_obs         0.0703
_reflns_number_observed          4815
_reflns_number_total             6554
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            a907658a.txt
_cod_data_source_block           cu2papno
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.8339P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.8339P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7008973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu1 Cu 0.85243(3) 1.30742(3) 0.121582(9) 0.02065(7) Uani 1 d . .
Cu2 Cu 0.33262(3) 0.81721(3) 0.191606(9) 0.02022(7) Uani 1 d . .
O1 O 1.0822(2) 1.2320(2) 0.16383(7) 0.0295(4) Uani 1 d . .
H11 H 1.0767(41) 1.1631(36) 0.1690(13) 0.045(12) Uiso 1 d . .
H10 H 1.1959(34) 1.2431(34) 0.1410(11) 0.042(8) Uiso 1 d . .
O2 O 0.8433(3) 1.4666(2) 0.17038(7) 0.0375(5) Uani 1 d . .
H20 H 0.7588(36) 1.4909(35) 0.1681(11) 0.036(9) Uiso 1 d . .
H21 H 0.8914(45) 1.5411(48) 0.1639(14) 0.076(13) Uiso 1 d . .
O3 O 0.3070(2) 0.8957(2) 0.25536(6) 0.0273(4) Uani 1 d . .
H30 H 0.2341(40) 0.9463(39) 0.2584(12) 0.054(11) Uiso 1 d . .
H31 H 0.3351(37) 0.8420(37) 0.2792(12) 0.046(9) Uiso 1 d . .
O4 O 0.9838(2) 1.4358(2) 0.08660(6) 0.0263(3) Uani 1 d . .
O5 O 0.7597(2) 1.5190(2) 0.05401(7) 0.0398(4) Uani 1 d . .
O6 O 0.9695(2) 1.6293(2) 0.03977(8) 0.0481(5) Uani 1 d . .
O7 O 0.1190(7) 0.7172(7) 0.1807(3) 0.0276(10) Uani 0.80 d P 1
O8 O 0.0713(4) 0.9276(4) 0.14376(13) 0.0337(7) Uani 0.80 d P 1
O9 O -0.1126(9) 0.7654(4) 0.1454(3) 0.0350(10) Uani 0.80 d P 1
O10 O 0.3984(2) 0.6121(2) 0.23083(6) 0.0256(3) Uani 1 d . .
O11 O 0.6212(2) 0.6384(2) 0.20546(7) 0.0371(4) Uani 1 d . .
O12 O 0.5875(2) 0.4624(2) 0.25660(6) 0.0321(4) Uani 1 d . .
O13 O 1.4077(3) 1.3705(2) 0.15343(7) 0.0502(5) Uani 1 d . .
O14 O 1.4973(2) 1.3198(2) 0.08527(7) 0.0461(5) Uani 1 d . .
O15 O 1.2881(3) 1.2114(3) 0.10293(8) 0.0553(6) Uani 1 d . .
N1 N 0.8128(2) 1.1485(2) 0.06994(7) 0.0201(4) Uani 1 d . .
N2 N 0.7191(2) 1.1712(2) 0.15702(6) 0.0190(3) Uani 1 d . .
N3 N 0.4994(2) 0.9751(2) 0.18521(6) 0.0200(4) Uani 1 d . .
N4 N 0.3796(2) 0.7586(2) 0.12589(6) 0.0206(4) Uani 1 d . .
N5 N 0.9012(2) 1.5320(2) 0.05896(7) 0.0256(4) Uani 1 d . .
N6 N 0.0232(2) 0.8056(2) 0.15703(7) 0.0242(4) Uani 1 d . .
N7 N 0.5390(2) 0.5689(2) 0.23096(7) 0.0240(4) Uani 1 d . .
N8 N 1.3997(3) 1.3036(3) 0.11400(8) 0.0377(5) Uani 1 d . .
C1 C 0.8609(3) 1.1428(3) 0.02616(8) 0.0241(5) Uani 1 d . .
H1 H 0.9287(3) 1.2151(3) 0.01792(8) 0.029 Uiso 1 d R .
C2 C 0.8118(3) 1.0303(3) -0.00761(8) 0.0253(5) Uani 1 d . .
H2 H 0.8470(3) 1.0290(3) -0.03777(8) 0.030 Uiso 1 d R .
C3 C 0.7111(2) 0.9219(3) 0.00380(8) 0.0233(4) Uani 1 d . .
H3 H 0.6790(2) 0.8469(3) -0.01843(8) 0.028 Uiso 1 d R .
C4 C 0.6574(2) 0.9257(2) 0.04939(8) 0.0195(4) Uani 1 d . .
C5 C 0.7136(2) 1.0412(2) 0.08094(7) 0.0186(4) Uani 1 d . .
C6 C 0.6633(2) 1.0558(2) 0.12816(7) 0.0182(4) Uani 1 d . .
C7 C 0.6655(2) 1.1859(2) 0.19925(7) 0.0206(4) Uani 1 d . .
H7 H 0.7020(2) 1.2632(2) 0.22002(7) 0.025 Uiso 1 d R .
C8 C 0.5542(3) 1.0870(2) 0.21351(8) 0.0213(4) Uani 1 d . .
H8 H 0.5187(3) 1.1008(2) 0.24331(8) 0.026 Uiso 1 d R .
C9 C 0.5550(2) 0.9591(2) 0.14199(7) 0.0182(4) Uani 1 d . .
C10 C 0.4923(2) 0.8421(2) 0.10979(8) 0.0189(4) Uani 1 d . .
C11 C 0.5428(2) 0.8222(2) 0.06428(8) 0.0192(4) Uani 1 d . .
C12 C 0.4730(3) 0.7052(2) 0.03509(8) 0.0225(4) Uani 1 d . .
H12 H 0.5031(3) 0.6854(2) 0.00484(8) 0.027 Uiso 1 d R .
C13 C 0.3602(3) 0.6209(2) 0.05184(8) 0.0244(5) Uani 1 d . .
H13 H 0.3140(3) 0.5437(2) 0.03278(8) 0.029 Uiso 1 d R .
C14 C 0.3144(3) 0.6503(2) 0.09716(8) 0.0233(4) Uani 1 d . .
H14 H 0.2368(3) 0.5930(2) 0.10764(8) 0.028 Uiso 1 d R .
O81 O 0.1201(15) 0.9128(16) 0.1605(5) 0.027(2) Uani 0.20 d P 2
O71 O 0.0830(27) 0.6861(28) 0.1814(12) 0.028(4) Uani 0.20 d P 2
O91 O -0.1120(34) 0.8159(18) 0.1429(11) 0.033(4) Uani 0.20 d P 2
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'
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
O4 Cu1 O2 89.60(8) . . ?
O4 Cu1 N1 96.95(7) . . ?
O2 Cu1 N1 167.93(9) . . ?
O4 Cu1 N2 178.77(7) . . ?
O2 Cu1 N2 91.51(8) . . ?
N1 Cu1 N2 82.05(7) . . ?
O4 Cu1 O1 84.03(7) . . ?
O2 Cu1 O1 89.05(9) . . ?
N1 Cu1 O1 101.67(7) . . ?
N2 Cu1 O1 95.46(7) . . ?
O4 Cu1 O5 52.28(6) . . ?
O2 Cu1 O5 85.69(8) . . ?
N1 Cu1 O5 90.30(7) . . ?
N2 Cu1 O5 128.34(6) . . ?
O1 Cu1 O5 135.95(7) . . ?
O3 Cu2 N4 172.27(8) . . ?
O3 Cu2 O7 94.3(2) . . ?
N4 Cu2 O7 92.8(2) . . ?
O3 Cu2 N3 90.05(7) . . ?
N4 Cu2 N3 82.23(7) . . ?
O7 Cu2 N3 158.1(2) . . ?
O3 Cu2 O81 90.8(4) . . ?
N4 Cu2 O81 91.1(4) . . ?
N3 Cu2 O81 105.9(4) . . ?
O3 Cu2 O10 84.94(7) . . ?
N4 Cu2 O10 99.03(7) . . ?
O7 Cu2 O10 82.6(2) . . ?
N3 Cu2 O10 119.22(6) . . ?
O81 Cu2 O10 134.6(4) . . ?
O3 Cu2 O71 93.7(7) . . ?
N4 Cu2 O71 93.5(7) . . ?
N3 Cu2 O71 161.2(7) . . ?
O81 Cu2 O71 55.7(8) . . ?
O10 Cu2 O71 79.5(7) . . ?
O3 Cu2 O8 96.62(10) . . ?
N4 Cu2 O8 85.26(10) . . ?
O7 Cu2 O8 52.7(2) . . ?
N3 Cu2 O8 105.41(9) . . ?
O10 Cu2 O8 135.35(9) . . ?
O3 Cu2 O11 106.53(7) . . ?
N4 Cu2 O11 72.16(6) . . ?
O7 Cu2 O11 121.2(2) . . ?
N3 Cu2 O11 77.76(6) . . ?
O81 Cu2 O11 162.4(4) . . ?
O10 Cu2 O11 46.89(5) . . ?
O71 Cu2 O11 118.5(7) . . ?
O8 Cu2 O11 156.69(9) . . ?
Cu1 O1 H11 108.3(33) . . ?
Cu1 O1 H10 114.9(13) . . ?
H11 O1 H10 106.2(36) . . ?
Cu1 O2 H20 106.4(24) . . ?
Cu1 O2 H21 111.7(28) . . ?
H20 O2 H21 105.4(35) . . ?
Cu2 O3 H30 120.0(24) . . ?
Cu2 O3 H31 116.9(22) . . ?
H30 O3 H31 113.7(32) . . ?
N5 O4 Cu1 111.42(13) . . ?
N5 O5 Cu1 78.05(13) . . ?
N6 O7 Cu2 108.6(3) . . ?
N6 O8 Cu2 79.9(2) . . ?
N7 O10 Cu2 116.22(13) . . ?
N7 O11 Cu2 78.43(12) . . ?
N8 O15 H10 100.4(12) . . ?
C1 N1 C5 117.9(2) . . ?
C1 N1 Cu1 128.6(2) . . ?
C5 N1 Cu1 113.30(14) . . ?
C7 N2 C6 117.0(2) . . ?
C7 N2 Cu1 131.43(15) . . ?
C6 N2 Cu1 111.05(13) . . ?
C8 N3 C9 117.2(2) . . ?
C8 N3 Cu2 132.44(15) . . ?
C9 N3 Cu2 110.28(14) . . ?
C14 N4 C10 118.4(2) . . ?
C14 N4 Cu2 127.78(15) . . ?
C10 N4 Cu2 113.86(14) . . ?
O6 N5 O5 124.3(2) . . ?
O6 N5 O4 117.9(2) . . ?
O5 N5 O4 117.8(2) . . ?
O9 N6 O8 122.0(3) . . ?
O9 N6 O7 119.2(3) . . ?
O8 N6 O7 118.7(3) . . ?
O91 N6 O81 125.4(9) . . ?
O91 N6 O71 121.7(12) . . ?
O81 N6 O71 111.2(11) . . ?
O12 N7 O11 122.7(2) . . ?
O12 N7 O10 119.1(2) . . ?
O11 N7 O10 118.2(2) . . ?
O13 N8 O14 122.9(3) . . ?
O13 N8 O15 118.1(2) . . ?
O14 N8 O15 119.0(2) . . ?
N1 C1 C2 121.7(2) . . ?
N1 C1 H1 119.18(13) . . ?
C2 C1 H1 119.15(13) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.92(13) . . ?
C1 C2 H2 119.92(13) . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.28(13) . . ?
C4 C3 H3 120.24(13) . . ?
C5 C4 C3 116.4(2) . . ?
C5 C4 C11 119.2(2) . . ?
C3 C4 C11 124.3(2) . . ?
N1 C5 C4 124.4(2) . . ?
N1 C5 C6 115.1(2) . . ?
C4 C5 C6 120.5(2) . . ?
N2 C6 C9 121.5(2) . . ?
N2 C6 C5 118.2(2) . . ?
C9 C6 C5 120.2(2) . . ?
N2 C7 C8 121.7(2) . . ?
N2 C7 H7 119.15(12) . . ?
C8 C7 H7 119.18(12) . . ?
N3 C8 C7 121.3(2) . . ?
N3 C8 H8 119.27(12) . . ?
C7 C8 H8 119.48(12) . . ?
N3 C9 C6 121.4(2) . . ?
N3 C9 C10 118.1(2) . . ?
C6 C9 C10 120.4(2) . . ?
N4 C10 C11 123.8(2) . . ?
N4 C10 C9 115.5(2) . . ?
C11 C10 C9 120.7(2) . . ?
C10 C11 C12 116.4(2) . . ?
C10 C11 C4 118.9(2) . . ?
C12 C11 C4 124.7(2) . . ?
C13 C12 C11 119.4(2) . . ?
C13 C12 H12 120.33(13) . . ?
C11 C12 H12 120.30(13) . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.73(13) . . ?
C14 C13 H13 119.69(13) . . ?
N4 C14 C13 121.5(2) . . ?
N4 C14 H14 119.17(12) . . ?
C13 C14 H14 119.33(13) . . ?
N6 O81 Cu2 104.9(7) . . ?
N6 O71 Cu2 87.0(8) . . ?
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
Cu1 O4 1.977(2) . ?
Cu1 O2 1.980(2) . ?
Cu1 N1 2.018(2) . ?
Cu1 N2 2.037(2) . ?
Cu1 O1 2.278(2) . ?
Cu1 O5 2.713(2) . ?
Cu2 O3 1.944(2) . ?
Cu2 N4 1.992(2) . ?
Cu2 O7 2.055(5) . ?
Cu2 N3 2.062(2) . ?
Cu2 O81 2.115(11) . ?
Cu2 O10 2.179(2) . ?
Cu2 O71 2.46(2) . ?
Cu2 O8 2.664(3) . ?
Cu2 O11 2.969(2) . ?
O1 H11 0.64(3) . ?
O1 H10 1.25(3) . ?
O2 H20 0.76(3) . ?
O2 H21 0.82(4) . ?
O3 H30 0.80(4) . ?
O3 H31 0.83(3) . ?
O4 N5 1.304(2) . ?
O5 N5 1.230(3) . ?
O6 N5 1.223(3) . ?
O7 N6 1.268(8) . ?
O8 N6 1.250(4) . ?
O9 N6 1.238(7) . ?
O10 N7 1.288(2) . ?
O11 N7 1.245(2) . ?
O12 N7 1.232(2) . ?
O13 N8 1.240(3) . ?
O14 N8 1.254(3) . ?
O15 N8 1.284(3) . ?
N1 C1 1.339(3) . ?
N1 C5 1.361(3) . ?
N2 C7 1.326(3) . ?
N2 C6 1.358(3) . ?
N3 C8 1.324(3) . ?
N3 C9 1.361(3) . ?
N4 C14 1.334(3) . ?
N4 C10 1.363(3) . ?
N6 O91 1.19(3) . ?
N6 O81 1.278(14) . ?
N6 O71 1.34(3) . ?
C1 C2 1.404(3) . ?
C1 H1 0.93 . ?
C2 C3 1.380(3) . ?
C2 H2 0.93 . ?
C3 C4 1.408(3) . ?
C3 H3 0.93 . ?
C4 C5 1.402(3) . ?
C4 C11 1.469(3) . ?
C5 C6 1.443(3) . ?
C6 C9 1.380(3) . ?
C7 C8 1.415(3) . ?
C7 H7 0.93 . ?
C8 H8 0.93 . ?
C9 C10 1.438(3) . ?
C10 C11 1.404(3) . ?
C11 C12 1.412(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.93 . ?
C13 C14 1.395(3) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
