#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229973.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_2229973
loop_
_publ_author_name
'Muller, Fabian M. A.'
'Muller, Theunis J.'
'Steyl, Gideon'
_publ_section_title
;
 (2-Methyl-4-oxo-4H-pyran-3-olato-κ²O³,O⁴)bis(triphenylphosphane-κP)copper(I)--triphenylphosphane--methanol
 (1/1/1)
;
_journal_coeditor_code           FI2105
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m581
_journal_page_last               m582
_journal_paper_doi               10.1107/S1600536811011470
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac
'[Cu (C6 H5 O3) (C18 H15 P)2], C18 H15 P, C H4 O'
_chemical_formula_moiety         'C42 H35 Cu O3 P2, C18 H15 P, C H4 O'
_chemical_formula_sum            'C61 H54 Cu O4 P3'
_chemical_formula_weight         1007.49
_chemical_name_systematic
'(2-Methyl-4-oxo-4H-pyran-3-olato-κ²O³,O⁴)bis(triphenylphosphane-κP)copper(I)--triphenylphosphane--methanol (1/1/1)'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 119.2050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5253(7)
_cell_length_b                   13.5716(4)
_cell_length_c                   20.3129(7)
_cell_measurement_reflns_used    8938
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.27
_cell_volume                     4939.1(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2007)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker X8 APEXII 4K'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0577
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58551
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         27
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.507
_refine_diff_density_min         -0.855
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         10787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+7.9566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                8326
_reflns_number_total             10787
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fi2105.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229973
_cod_database_fobs_code          2229973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.214103(18) 0.00326(2) 0.261886(19) 0.01908(9) Uani d . 1 . .
P P1 0.10439(4) 0.06950(5) 0.22835(4) 0.01542(14) Uani d . 1 . .
P P2 0.23466(4) -0.16169(5) 0.26969(4) 0.01741(15) Uani d . 1 . .
P P3 0.38902(4) 0.48977(6) 0.31013(4) 0.02500(17) Uani d . 1 . .
O O1 0.29079(11) 0.06514(16) 0.23758(11) 0.0265(5) Uani d . 1 . .
O O2 0.29997(11) 0.04399(15) 0.37487(11) 0.0245(4) Uani d . 1 . .
C C1 0.08207(15) 0.08316(18) 0.30441(15) 0.0164(5) Uani d . 1 . .
C C2 0.14009(15) 0.08692(19) 0.37862(16) 0.0199(6) Uani d . 1 . .
H H2 0.1903 0.0819 0.3888 0.024 Uiso calc R 1 . .
C C6 0.00836(15) 0.09007(18) 0.29104(15) 0.0170(5) Uani d . 1 . .
H H6 -0.0319 0.0861 0.2409 0.02 Uiso calc R 1 . .
C C5 -0.00614(15) 0.10258(19) 0.35027(16) 0.0186(5) Uani d . 1 . .
H H5 -0.0562 0.1091 0.3405 0.022 Uiso calc R 1 . .
C C3 0.12498(16) 0.0979(2) 0.43784(16) 0.0217(6) Uani d . 1 . .
H H3 0.1649 0.1001 0.4883 0.026 Uiso calc R 1 . .
C C4 0.05204(16) 0.1056(2) 0.42358(16) 0.0210(6) Uani d . 1 . .
H H4 0.0419 0.113 0.4642 0.025 Uiso calc R 1 . .
C C7 0.20878(15) -0.2199(2) 0.33478(16) 0.0202(6) Uani d . 1 . .
C C8 0.18613(16) -0.3169(2) 0.33070(17) 0.0261(6) Uani d . 1 . .
H H8 0.1824 -0.358 0.2911 0.031 Uiso calc R 1 . .
C C10 0.17415(17) -0.2963(2) 0.44152(18) 0.0298(7) Uani d . 1 . .
H H10 0.1616 -0.3219 0.4774 0.036 Uiso calc R 1 . .
C C9 0.16883(16) -0.3550(2) 0.38402(17) 0.0291(7) Uani d . 1 . .
H H9 0.1533 -0.4216 0.3806 0.035 Uiso calc R 1 . .
C C12 0.21461(19) -0.1614(2) 0.39378(19) 0.0316(7) Uani d . 1 . .
H H12 0.2302 -0.0947 0.3976 0.038 Uiso calc R 1 . .
C C11 0.1978(2) -0.2001(3) 0.4469(2) 0.0361(8) Uani d . 1 . .
H H11 0.2026 -0.16 0.4874 0.043 Uiso calc R 1 . .
C C14 0.22245(15) -0.3304(2) 0.18224(16) 0.0206(6) Uani d . 1 . .
H H14 0.2683 -0.3519 0.2234 0.025 Uiso calc R 1 . .
C C13 0.19240(15) -0.2392(2) 0.18613(15) 0.0185(5) Uani d . 1 . .
C C18 0.12553(15) -0.2083(2) 0.12403(16) 0.0193(6) Uani d . 1 . .
H H18 0.1048 -0.1462 0.1254 0.023 Uiso calc R 1 . .
C C17 0.08922(15) -0.2673(2) 0.06064(16) 0.0215(6) Uani d . 1 . .
H H17 0.044 -0.2455 0.0187 0.026 Uiso calc R 1 . .
C C15 0.18590(16) -0.3892(2) 0.11902(16) 0.0217(6) Uani d . 1 . .
H H15 0.2067 -0.451 0.1171 0.026 Uiso calc R 1 . .
C C16 0.11908(16) -0.3586(2) 0.05846(16) 0.0216(6) Uani d . 1 . .
H H16 0.0937 -0.3998 0.0155 0.026 Uiso calc R 1 . .
C C23 -0.05007(16) -0.1488(2) 0.13305(17) 0.0223(6) Uani d . 1 . .
H H23 -0.0624 -0.2075 0.15 0.027 Uiso calc R 1 . .
C C19 0.02499(14) -0.00172(19) 0.15983(15) 0.0159(5) Uani d . 1 . .
C C24 0.00684(15) -0.08956(19) 0.18378(16) 0.0196(6) Uani d . 1 . .
H H24 0.034 -0.1083 0.2353 0.023 Uiso calc R 1 . .
C C20 -0.01466(16) 0.0231(2) 0.08419(16) 0.0219(6) Uani d . 1 . .
H H20 -0.0029 0.082 0.067 0.026 Uiso calc R 1 . .
C C22 -0.08934(17) -0.1231(2) 0.05755(18) 0.0265(6) Uani d . 1 . .
H H22 -0.1284 -0.1643 0.0226 0.032 Uiso calc R 1 . .
C C21 -0.07135(17) -0.0373(2) 0.03344(17) 0.0262(6) Uani d . 1 . .
H H21 -0.0981 -0.0195 -0.0183 0.031 Uiso calc R 1 . .
C C27 0.37303(16) -0.2392(2) 0.37962(17) 0.0264(6) Uani d . 1 . .
H H27 0.3475 -0.2627 0.4049 0.032 Uiso calc R 1 . .
C C25 0.33395(14) -0.19082(19) 0.31180(15) 0.0183(5) Uani d . 1 . .
C C26 0.37255(17) -0.1562(2) 0.27614(19) 0.0308(7) Uani d . 1 . .
H H26 0.3466 -0.1217 0.2297 0.037 Uiso calc R 1 . .
C C28 0.44955(17) -0.2538(3) 0.41136(18) 0.0333(7) Uani d . 1 . .
H H28 0.4759 -0.2875 0.4581 0.04 Uiso calc R 1 . .
C C29 0.48730(17) -0.2200(2) 0.3756(2) 0.0333(7) Uani d . 1 . .
H H29 0.5396 -0.23 0.3974 0.04 Uiso calc R 1 . .
C C30 0.44870(18) -0.1718(3) 0.3081(2) 0.0364(8) Uani d . 1 . .
H H30 0.4744 -0.1488 0.2829 0.044 Uiso calc R 1 . .
C C31 0.08839(15) 0.19196(18) 0.18591(15) 0.0165(5) Uani d . 1 . .
C C34 0.07028(16) 0.3770(2) 0.11999(15) 0.0208(6) Uani d . 1 . .
H H34 0.0645 0.4404 0.098 0.025 Uiso calc R 1 . .
C C35 0.02073(15) 0.34515(19) 0.14352(15) 0.0187(5) Uani d . 1 . .
H H35 -0.0192 0.3865 0.1374 0.022 Uiso calc R 1 . .
C C36 0.02951(15) 0.25301(19) 0.17593(15) 0.0181(5) Uani d . 1 . .
H H36 -0.0048 0.2311 0.1915 0.022 Uiso calc R 1 . .
C C32 0.13759(15) 0.2245(2) 0.16215(16) 0.0211(6) Uani d . 1 . .
H H32 0.178 0.1837 0.1689 0.025 Uiso calc R 1 . .
C C33 0.12819(16) 0.3166(2) 0.12855(17) 0.0233(6) Uani d . 1 . .
H H33 0.1615 0.3379 0.1115 0.028 Uiso calc R 1 . .
C C42 0.33225(16) 0.4130(2) 0.33699(16) 0.0214(6) Uani d . 1 . .
C C41 0.25678(17) 0.4336(2) 0.30419(18) 0.0285(7) Uani d . 1 . .
H H41 0.2355 0.4815 0.2652 0.034 Uiso calc R 1 . .
C C40 0.21165(17) 0.3860(2) 0.32715(19) 0.0314(7) Uani d . 1 . .
H H40 0.1598 0.4004 0.3033 0.038 Uiso calc R 1 . .
C C39 0.24148(18) 0.3180(2) 0.3842(2) 0.0328(7) Uani d . 1 . .
H H39 0.2107 0.2857 0.4004 0.039 Uiso calc R 1 . .
C C38 0.3168(2) 0.2969(3) 0.4180(2) 0.0418(9) Uani d . 1 . .
H H38 0.3381 0.2505 0.458 0.05 Uiso calc R 1 . .
C C37 0.36142(19) 0.3430(3) 0.3936(2) 0.0378(8) Uani d . 1 . .
H H37 0.4128 0.3263 0.4162 0.045 Uiso calc R 1 . .
C C44 0.50530(17) 0.3496(2) 0.34617(19) 0.0327(7) Uani d . 1 . .
H H44 0.472 0.3155 0.3014 0.039 Uiso calc R 1 . .
C C43 0.48189(16) 0.4346(2) 0.36526(17) 0.0263(6) Uani d . 1 . .
C C45 0.57669(18) 0.3128(3) 0.3913(2) 0.0374(8) Uani d . 1 . .
H H45 0.5924 0.2551 0.3765 0.045 Uiso calc R 1 . .
C C46 0.62451(18) 0.3596(3) 0.45730(19) 0.0388(8) Uani d . 1 . .
H H46 0.673 0.3337 0.4888 0.047 Uiso calc R 1 . .
C C47 0.60193(19) 0.4443(3) 0.4778(2) 0.0451(9) Uani d . 1 . .
H H47 0.6348 0.4766 0.5237 0.054 Uiso calc R 1 . .
C C48 0.53168(18) 0.4823(3) 0.43178(19) 0.0371(8) Uani d . 1 . .
H H48 0.5171 0.5417 0.4456 0.045 Uiso calc R 1 . .
C C49 0.36127(16) 0.4483(2) 0.21457(17) 0.0283(7) Uani d . 1 . .
C C54 0.33106(17) 0.3582(3) 0.18496(18) 0.0318(7) Uani d . 1 . .
H H54 0.3235 0.3112 0.2153 0.038 Uiso calc R 1 . .
C C51 0.35207(18) 0.4942(3) 0.0952(2) 0.0396(8) Uani d . 1 . .
H H51 0.3591 0.5409 0.0644 0.048 Uiso calc R 1 . .
C C50 0.37123(17) 0.5176(3) 0.16850(19) 0.0337(7) Uani d . 1 . .
H H50 0.3913 0.5807 0.1881 0.04 Uiso calc R 1 . .
C C52 0.32287(18) 0.4032(3) 0.06709(19) 0.0362(8) Uani d . 1 . .
H H52 0.3105 0.387 0.0168 0.043 Uiso calc R 1 . .
C C53 0.31113(18) 0.3348(3) 0.1100(2) 0.0373(8) Uani d . 1 . .
H H53 0.2898 0.2726 0.0893 0.045 Uiso calc R 1 . .
C C55 0.35473(16) 0.0786(2) 0.29884(17) 0.0236(6) Uani d . 1 . .
C C59 0.41971(16) 0.0984(2) 0.29795(18) 0.0282(7) Uani d . 1 . .
C C60 0.42869(18) 0.1052(3) 0.2299(2) 0.0363(8) Uani d . 1 . .
H H60A 0.4396 0.0398 0.2174 0.054 Uiso calc R 1 . .
H H60B 0.4699 0.1501 0.2399 0.054 Uiso calc R 1 . .
H H60C 0.3825 0.1303 0.1875 0.054 Uiso calc R 1 . .
C C57 0.42829(17) 0.0856(2) 0.43665(19) 0.0304(7) Uani d . 1 . .
H H57 0.4327 0.0833 0.4854 0.036 Uiso calc R 1 . .
C C58 0.48828(18) 0.1051(3) 0.42923(19) 0.0348(7) Uani d . 1 . .
H H58 0.5347 0.1156 0.4736 0.042 Uiso calc R 1 . .
C C56 0.35775(16) 0.0683(2) 0.37156(17) 0.0236(6) Uani d . 1 . .
O O3 0.48634(12) 0.11061(17) 0.36300(13) 0.0350(5) Uani d . 1 . .
O O4 0.24131(15) 0.1036(2) 0.09364(14) 0.0463(6) Uani d . 1 . .
H H4A 0.2582 0.0956 0.1402 0.069 Uiso calc R 1 . .
C C61 0.2624(3) 0.0252(4) 0.0650(3) 0.0755(16) Uani d . 1 . .
H H61A 0.3164 0.0274 0.0843 0.113 Uiso calc R 1 . .
H H61B 0.2365 0.0293 0.0098 0.113 Uiso calc R 1 . .
H H61C 0.2491 -0.0367 0.0804 0.113 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O2 . . 80.07(8) ?
O1 Cu1 P1 . . 123.30(6) ?
O2 Cu1 P1 . . 113.74(6) ?
O1 Cu1 P2 . . 106.44(6) ?
O2 Cu1 P2 . . 98.61(6) ?
P1 Cu1 P2 . . 123.49(3) ?
C19 P1 C1 . . 101.57(12) ?
C19 P1 C31 . . 103.56(12) ?
C1 P1 C31 . . 104.23(12) ?
C19 P1 Cu1 . . 114.75(8) ?
C1 P1 Cu1 . . 114.93(9) ?
C31 P1 Cu1 . . 116.03(9) ?
C13 P2 C7 . . 104.53(13) ?
C13 P2 C25 . . 103.13(12) ?
C7 P2 C25 . . 102.67(12) ?
C13 P2 Cu1 . . 121.19(9) ?
C7 P2 Cu1 . . 111.53(9) ?
C25 P2 Cu1 . . 111.90(9) ?
C49 P3 C42 . . 103.15(14) ?
C49 P3 C43 . . 102.45(14) ?
C42 P3 C43 . . 102.04(13) ?
C55 O1 Cu1 . . 111.17(18) ?
C56 O2 Cu1 . . 107.97(18) ?
C2 C1 C6 . . 118.6(2) ?
C2 C1 P1 . . 119.0(2) ?
C6 C1 P1 . . 122.4(2) ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C5 C6 C1 . . 120.6(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C4 C5 C6 . . 120.1(3) ?
C4 C5 H5 . . 120 ?
C6 C5 H5 . . 120 ?
C4 C3 C2 . . 120.2(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 120.1(3) ?
C5 C4 H4 . . 120 ?
C3 C4 H4 . . 120 ?
C8 C7 C12 . . 118.6(3) ?
C8 C7 P2 . . 125.1(2) ?
C12 C7 P2 . . 116.3(2) ?
C7 C8 C9 . . 120.7(3) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C9 C10 C11 . . 119.7(3) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C10 C9 C8 . . 120.1(3) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C11 C12 C7 . . 120.3(3) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
C10 C11 C12 . . 120.6(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C15 C14 C13 . . 120.5(3) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C18 C13 C14 . . 118.5(3) ?
C18 C13 P2 . . 118.7(2) ?
C14 C13 P2 . . 122.7(2) ?
C17 C18 C13 . . 120.7(3) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
C18 C17 C16 . . 119.9(3) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C14 C15 C16 . . 120.3(3) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C15 C16 C17 . . 119.9(3) ?
C15 C16 H16 . . 120 ?
C17 C16 H16 . . 120 ?
C24 C23 C22 . . 120.3(3) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C20 C19 C24 . . 118.6(3) ?
C20 C19 P1 . . 122.8(2) ?
C24 C19 P1 . . 118.4(2) ?
C23 C24 C19 . . 120.5(3) ?
C23 C24 H24 . . 119.8 ?
C19 C24 H24 . . 119.8 ?
C19 C20 C21 . . 120.5(3) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C21 C22 C23 . . 119.5(3) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C22 C21 C20 . . 120.5(3) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C25 C27 C28 . . 120.5(3) ?
C25 C27 H27 . . 119.8 ?
C28 C27 H27 . . 119.8 ?
C27 C25 C26 . . 118.7(3) ?
C27 C25 P2 . . 123.0(2) ?
C26 C25 P2 . . 118.2(2) ?
C30 C26 C25 . . 120.3(3) ?
C30 C26 H26 . . 119.9 ?
C25 C26 H26 . . 119.9 ?
C29 C28 C27 . . 120.5(3) ?
C29 C28 H28 . . 119.7 ?
C27 C28 H28 . . 119.7 ?
C30 C29 C28 . . 119.3(3) ?
C30 C29 H29 . . 120.4 ?
C28 C29 H29 . . 120.4 ?
C29 C30 C26 . . 120.7(3) ?
C29 C30 H30 . . 119.6 ?
C26 C30 H30 . . 119.6 ?
C32 C31 C36 . . 119.1(2) ?
C32 C31 P1 . . 117.4(2) ?
C36 C31 P1 . . 123.5(2) ?
C33 C34 C35 . . 120.1(2) ?
C33 C34 H34 . . 120 ?
C35 C34 H34 . . 120 ?
C36 C35 C34 . . 119.9(3) ?
C36 C35 H35 . . 120 ?
C34 C35 H35 . . 120 ?
C35 C36 C31 . . 120.5(2) ?
C35 C36 H36 . . 119.7 ?
C31 C36 H36 . . 119.7 ?
C31 C32 C33 . . 120.4(3) ?
C31 C32 H32 . . 119.8 ?
C33 C32 H32 . . 119.8 ?
C34 C33 C32 . . 120.0(3) ?
C34 C33 H33 . . 120 ?
C32 C33 H33 . . 120 ?
C37 C42 C41 . . 117.9(3) ?
C37 C42 P3 . . 123.9(2) ?
C41 C42 P3 . . 117.8(2) ?
C42 C41 C40 . . 121.3(3) ?
C42 C41 H41 . . 119.4 ?
C40 C41 H41 . . 119.4 ?
C39 C40 C41 . . 120.2(3) ?
C39 C40 H40 . . 119.9 ?
C41 C40 H40 . . 119.9 ?
C40 C39 C38 . . 119.3(3) ?
C40 C39 H39 . . 120.3 ?
C38 C39 H39 . . 120.3 ?
C39 C38 C37 . . 120.3(3) ?
C39 C38 H38 . . 119.9 ?
C37 C38 H38 . . 119.9 ?
C42 C37 C38 . . 121.0(3) ?
C42 C37 H37 . . 119.5 ?
C38 C37 H37 . . 119.5 ?
C43 C44 C45 . . 121.1(3) ?
C43 C44 H44 . . 119.4 ?
C45 C44 H44 . . 119.4 ?
C44 C43 C48 . . 118.1(3) ?
C44 C43 P3 . . 124.9(2) ?
C48 C43 P3 . . 117.1(2) ?
C46 C45 C44 . . 120.0(3) ?
C46 C45 H45 . . 120 ?
C44 C45 H45 . . 120 ?
C45 C46 C47 . . 119.8(3) ?
C45 C46 H46 . . 120.1 ?
C47 C46 H46 . . 120.1 ?
C46 C47 C48 . . 120.0(3) ?
C46 C47 H47 . . 120 ?
C48 C47 H47 . . 120 ?
C47 C48 C43 . . 120.9(3) ?
C47 C48 H48 . . 119.5 ?
C43 C48 H48 . . 119.5 ?
C54 C49 C50 . . 119.0(3) ?
C54 C49 P3 . . 125.6(3) ?
C50 C49 P3 . . 115.4(3) ?
C49 C54 C53 . . 120.4(3) ?
C49 C54 H54 . . 119.8 ?
C53 C54 H54 . . 119.8 ?
C52 C51 C50 . . 119.5(3) ?
C52 C51 H51 . . 120.2 ?
C50 C51 H51 . . 120.2 ?
C51 C50 C49 . . 120.4(3) ?
C51 C50 H50 . . 119.8 ?
C49 C50 H50 . . 119.8 ?
C51 C52 C53 . . 121.4(3) ?
C51 C52 H52 . . 119.3 ?
C53 C52 H52 . . 119.3 ?
C52 C53 C54 . . 119.1(3) ?
C52 C53 H53 . . 120.4 ?
C54 C53 H53 . . 120.4 ?
O1 C55 C59 . . 123.1(3) ?
O1 C55 C56 . . 118.6(2) ?
C59 C55 C56 . . 118.2(3) ?
C55 C59 O3 . . 122.1(3) ?
C55 C59 C60 . . 126.1(3) ?
O3 C59 C60 . . 111.8(3) ?
C59 C60 H60A . . 109.5 ?
C59 C60 H60B . . 109.5 ?
H60A C60 H60B . . 109.5 ?
C59 C60 H60C . . 109.5 ?
H60A C60 H60C . . 109.5 ?
H60B C60 H60C . . 109.5 ?
C58 C57 C56 . . 120.2(3) ?
C58 C57 H57 . . 119.9 ?
C56 C57 H57 . . 119.9 ?
O3 C58 C57 . . 123.4(3) ?
O3 C58 H58 . . 118.3 ?
C57 C58 H58 . . 118.3 ?
O2 C56 C57 . . 123.3(3) ?
O2 C56 C55 . . 120.2(3) ?
C57 C56 C55 . . 116.5(3) ?
C58 O3 C59 . . 119.5(3) ?
C61 O4 H4A . . 109.5 ?
O4 C61 H61A . . 109.5 ?
O4 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
O4 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 109.5 ?
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 O1 . 2.046(2) y
Cu1 O2 . 2.175(2) y
Cu1 P1 . 2.2014(7) y
Cu1 P2 . 2.2692(8) y
P1 C19 . 1.820(3) ?
P1 C1 . 1.823(3) ?
P1 C31 . 1.827(3) ?
P2 C13 . 1.817(3) ?
P2 C7 . 1.827(3) ?
P2 C25 . 1.828(3) ?
P3 C49 . 1.825(3) ?
P3 C42 . 1.833(3) ?
P3 C43 . 1.834(3) ?
O1 C55 . 1.308(4) y
O2 C56 . 1.264(3) y
C1 C2 . 1.393(4) ?
C1 C6 . 1.404(4) ?
C2 C3 . 1.389(4) ?
C2 H2 . 0.95 ?
C6 C5 . 1.384(4) ?
C6 H6 . 0.95 ?
C5 C4 . 1.382(4) ?
C5 H5 . 0.95 ?
C3 C4 . 1.383(4) ?
C3 H3 . 0.95 ?
C4 H4 . 0.95 ?
C7 C8 . 1.386(4) ?
C7 C12 . 1.393(4) ?
C8 C9 . 1.393(4) ?
C8 H8 . 0.95 ?
C10 C9 . 1.373(5) ?
C10 C11 . 1.379(5) ?
C10 H10 . 0.95 ?
C9 H9 . 0.95 ?
C12 C11 . 1.387(4) ?
C12 H12 . 0.95 ?
C11 H11 . 0.95 ?
C14 C15 . 1.382(4) ?
C14 C13 . 1.402(4) ?
C14 H14 . 0.95 ?
C13 C18 . 1.400(4) ?
C18 C17 . 1.385(4) ?
C18 H18 . 0.95 ?
C17 C16 . 1.392(4) ?
C17 H17 . 0.95 ?
C15 C16 . 1.386(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C23 C24 . 1.378(4) ?
C23 C22 . 1.384(4) ?
C23 H23 . 0.95 ?
C19 C20 . 1.384(4) ?
C19 C24 . 1.405(4) ?
C24 H24 . 0.95 ?
C20 C21 . 1.384(4) ?
C20 H20 . 0.95 ?
C22 C21 . 1.383(4) ?
C22 H22 . 0.95 ?
C21 H21 . 0.95 ?
C27 C25 . 1.376(4) ?
C27 C28 . 1.391(4) ?
C27 H27 . 0.95 ?
C25 C26 . 1.390(4) ?
C26 C30 . 1.386(4) ?
C26 H26 . 0.95 ?
C28 C29 . 1.374(5) ?
C28 H28 . 0.95 ?
C29 C30 . 1.370(5) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 C32 . 1.387(4) ?
C31 C36 . 1.396(4) ?
C34 C33 . 1.384(4) ?
C34 C35 . 1.387(4) ?
C34 H34 . 0.95 ?
C35 C36 . 1.383(4) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C32 C33 . 1.391(4) ?
C32 H32 . 0.95 ?
C33 H33 . 0.95 ?
C42 C37 . 1.383(4) ?
C42 C41 . 1.384(4) ?
C41 C40 . 1.384(4) ?
C41 H41 . 0.95 ?
C40 C39 . 1.370(5) ?
C40 H40 . 0.95 ?
C39 C38 . 1.382(5) ?
C39 H39 . 0.95 ?
C38 C37 . 1.384(5) ?
C38 H38 . 0.95 ?
C37 H37 . 0.95 ?
C44 C43 . 1.377(5) ?
C44 C45 . 1.388(4) ?
C44 H44 . 0.95 ?
C43 C48 . 1.393(5) ?
C45 C46 . 1.372(5) ?
C45 H45 . 0.95 ?
C46 C47 . 1.378(5) ?
C46 H46 . 0.95 ?
C47 C48 . 1.379(5) ?
C47 H47 . 0.95 ?
C48 H48 . 0.95 ?
C49 C54 . 1.370(5) ?
C49 C50 . 1.410(5) ?
C54 C53 . 1.407(5) ?
C54 H54 . 0.95 ?
C51 C52 . 1.371(5) ?
C51 C50 . 1.379(5) ?
C51 H51 . 0.95 ?
C50 H50 . 0.95 ?
C52 C53 . 1.372(5) ?
C52 H52 . 0.95 ?
C53 H53 . 0.95 ?
C55 C59 . 1.369(4) ?
C55 C56 . 1.455(4) ?
C59 O3 . 1.371(4) ?
C59 C60 . 1.483(5) ?
C60 H60A . 0.98 ?
C60 H60B . 0.98 ?
C60 H60C . 0.98 ?
C57 C58 . 1.338(5) ?
C57 C56 . 1.425(4) ?
C57 H57 . 0.95 ?
C58 O3 . 1.328(4) ?
C58 H58 . 0.95 ?
O4 C61 . 1.379(5) ?
O4 H4A . 0.84 ?
C61 H61A . 0.98 ?
C61 H61B . 0.98 ?
C61 H61C . 0.98 ?
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
O4 H4A O1 . 0.84 1.8 2.637(3) 174
C2 H2 O2 . 0.95 2.46 3.370(3) 162
C12 H12 O2 . 0.95 2.54 3.412(4) 153
C22 H22 O4 3 0.95 2.51 3.144(4) 125
C32 H32 O1 . 0.95 2.6 3.495(3) 158
C53 H53 O4 . 0.95 2.52 3.398(5) 154
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 Cu1 P1 C19 . . . . 114.17(12) ?
O2 Cu1 P1 C19 . . . . -152.19(11) ?
P2 Cu1 P1 C19 . . . . -33.04(10) ?
O1 Cu1 P1 C1 . . . . -128.58(12) ?
O2 Cu1 P1 C1 . . . . -34.94(11) ?
P2 Cu1 P1 C1 . . . . 84.21(10) ?
O1 Cu1 P1 C31 . . . . -6.66(13) ?
O2 Cu1 P1 C31 . . . . 86.98(11) ?
P2 Cu1 P1 C31 . . . . -153.88(10) ?
O1 Cu1 P2 C13 . . . . -85.70(12) ?
O2 Cu1 P2 C13 . . . . -167.81(11) ?
P1 Cu1 P2 C13 . . . . 66.15(11) ?
O1 Cu1 P2 C7 . . . . 150.65(11) ?
O2 Cu1 P2 C7 . . . . 68.54(11) ?
P1 Cu1 P2 C7 . . . . -57.51(10) ?
O1 Cu1 P2 C25 . . . . 36.28(12) ?
O2 Cu1 P2 C25 . . . . -45.84(11) ?
P1 Cu1 P2 C25 . . . . -171.88(10) ?
O2 Cu1 O1 C55 . . . . 12.32(19) ?
P1 Cu1 O1 C55 . . . . 124.29(17) ?
P2 Cu1 O1 C55 . . . . -83.80(19) ?
O1 Cu1 O2 C56 . . . . -11.20(18) ?
P1 Cu1 O2 C56 . . . . -133.33(17) ?
P2 Cu1 O2 C56 . . . . 94.12(18) ?
C19 P1 C1 C2 . . . . 147.6(2) ?
C31 P1 C1 C2 . . . . -105.0(2) ?
Cu1 P1 C1 C2 . . . . 23.1(2) ?
C19 P1 C1 C6 . . . . -32.4(2) ?
C31 P1 C1 C6 . . . . 75.0(2) ?
Cu1 P1 C1 C6 . . . . -156.94(18) ?
C6 C1 C2 C3 . . . . -0.4(4) ?
P1 C1 C2 C3 . . . . 179.6(2) ?
C2 C1 C6 C5 . . . . 1.4(4) ?
P1 C1 C6 C5 . . . . -178.6(2) ?
C1 C6 C5 C4 . . . . -1.8(4) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C6 C5 C4 C3 . . . . 1.1(4) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C13 P2 C7 C8 . . . . 20.2(3) ?
C25 P2 C7 C8 . . . . -87.2(3) ?
Cu1 P2 C7 C8 . . . . 152.8(2) ?
C13 P2 C7 C12 . . . . -161.6(2) ?
C25 P2 C7 C12 . . . . 91.0(2) ?
Cu1 P2 C7 C12 . . . . -29.0(2) ?
C12 C7 C8 C9 . . . . 0.6(4) ?
P2 C7 C8 C9 . . . . 178.8(2) ?
C11 C10 C9 C8 . . . . -1.0(5) ?
C7 C8 C9 C10 . . . . -0.1(4) ?
C8 C7 C12 C11 . . . . -0.2(5) ?
P2 C7 C12 C11 . . . . -178.5(3) ?
C9 C10 C11 C12 . . . . 1.5(5) ?
C7 C12 C11 C10 . . . . -0.9(5) ?
C15 C14 C13 C18 . . . . -1.3(4) ?
C15 C14 C13 P2 . . . . 176.2(2) ?
C7 P2 C13 C18 . . . . 100.7(2) ?
C25 P2 C13 C18 . . . . -152.3(2) ?
Cu1 P2 C13 C18 . . . . -26.2(2) ?
C7 P2 C13 C14 . . . . -76.8(2) ?
C25 P2 C13 C14 . . . . 30.2(3) ?
Cu1 P2 C13 C14 . . . . 156.28(19) ?
C14 C13 C18 C17 . . . . 1.0(4) ?
P2 C13 C18 C17 . . . . -176.6(2) ?
C13 C18 C17 C16 . . . . 0.3(4) ?
C13 C14 C15 C16 . . . . 0.2(4) ?
C14 C15 C16 C17 . . . . 1.2(4) ?
C18 C17 C16 C15 . . . . -1.4(4) ?
C1 P1 C19 C20 . . . . 132.2(2) ?
C31 P1 C19 C20 . . . . 24.3(3) ?
Cu1 P1 C19 C20 . . . . -103.2(2) ?
C1 P1 C19 C24 . . . . -52.8(2) ?
C31 P1 C19 C24 . . . . -160.7(2) ?
Cu1 P1 C19 C24 . . . . 71.9(2) ?
C22 C23 C24 C19 . . . . 1.0(4) ?
C20 C19 C24 C23 . . . . -1.0(4) ?
P1 C19 C24 C23 . . . . -176.3(2) ?
C24 C19 C20 C21 . . . . 0.5(4) ?
P1 C19 C20 C21 . . . . 175.5(2) ?
C24 C23 C22 C21 . . . . -0.4(4) ?
C23 C22 C21 C20 . . . . -0.2(4) ?
C19 C20 C21 C22 . . . . 0.1(4) ?
C28 C27 C25 C26 . . . . -0.6(4) ?
C28 C27 C25 P2 . . . . -175.9(2) ?
C13 P2 C25 C27 . . . . -112.7(3) ?
C7 P2 C25 C27 . . . . -4.2(3) ?
Cu1 P2 C25 C27 . . . . 115.5(2) ?
C13 P2 C25 C26 . . . . 72.0(3) ?
C7 P2 C25 C26 . . . . -179.5(2) ?
Cu1 P2 C25 C26 . . . . -59.8(2) ?
C27 C25 C26 C30 . . . . 1.0(5) ?
P2 C25 C26 C30 . . . . 176.5(3) ?
C25 C27 C28 C29 . . . . 0.2(5) ?
C27 C28 C29 C30 . . . . -0.2(5) ?
C28 C29 C30 C26 . . . . 0.6(5) ?
C25 C26 C30 C29 . . . . -1.0(5) ?
C19 P1 C31 C32 . . . . -112.3(2) ?
C1 P1 C31 C32 . . . . 141.8(2) ?
Cu1 P1 C31 C32 . . . . 14.4(2) ?
C19 P1 C31 C36 . . . . 67.2(2) ?
C1 P1 C31 C36 . . . . -38.7(3) ?
Cu1 P1 C31 C36 . . . . -166.1(2) ?
C33 C34 C35 C36 . . . . 0.3(4) ?
C34 C35 C36 C31 . . . . 0.6(4) ?
C32 C31 C36 C35 . . . . -0.7(4) ?
P1 C31 C36 C35 . . . . 179.8(2) ?
C36 C31 C32 C33 . . . . -0.3(4) ?
P1 C31 C32 C33 . . . . 179.2(2) ?
C35 C34 C33 C32 . . . . -1.3(4) ?
C31 C32 C33 C34 . . . . 1.3(4) ?
C49 P3 C42 C37 . . . . 114.1(3) ?
C43 P3 C42 C37 . . . . 8.1(3) ?
C49 P3 C42 C41 . . . . -73.1(3) ?
C43 P3 C42 C41 . . . . -179.1(2) ?
C37 C42 C41 C40 . . . . 0.0(5) ?
P3 C42 C41 C40 . . . . -173.2(3) ?
C42 C41 C40 C39 . . . . 1.1(5) ?
C41 C40 C39 C38 . . . . -0.6(5) ?
C40 C39 C38 C37 . . . . -0.9(6) ?
C41 C42 C37 C38 . . . . -1.5(5) ?
P3 C42 C37 C38 . . . . 171.3(3) ?
C39 C38 C37 C42 . . . . 2.0(6) ?
C45 C44 C43 C48 . . . . -0.8(5) ?
C45 C44 C43 P3 . . . . -179.9(2) ?
C49 P3 C43 C44 . . . . -27.5(3) ?
C42 P3 C43 C44 . . . . 79.1(3) ?
C49 P3 C43 C48 . . . . 153.4(3) ?
C42 P3 C43 C48 . . . . -100.1(3) ?
C43 C44 C45 C46 . . . . 2.0(5) ?
C44 C45 C46 C47 . . . . -1.3(5) ?
C45 C46 C47 C48 . . . . -0.5(5) ?
C46 C47 C48 C43 . . . . 1.8(6) ?
C44 C43 C48 C47 . . . . -1.1(5) ?
P3 C43 C48 C47 . . . . 178.1(3) ?
C42 P3 C49 C54 . . . . -23.6(3) ?
C43 P3 C49 C54 . . . . 82.1(3) ?
C42 P3 C49 C50 . . . . 155.1(2) ?
C43 P3 C49 C50 . . . . -99.2(2) ?
C50 C49 C54 C53 . . . . 0.8(4) ?
P3 C49 C54 C53 . . . . 179.4(2) ?
C52 C51 C50 C49 . . . . 0.3(5) ?
C54 C49 C50 C51 . . . . -1.2(5) ?
P3 C49 C50 C51 . . . . -179.9(2) ?
C50 C51 C52 C53 . . . . 1.0(5) ?
C51 C52 C53 C54 . . . . -1.4(5) ?
C49 C54 C53 C52 . . . . 0.5(5) ?
Cu1 O1 C55 C59 . . . . 165.3(2) ?
Cu1 O1 C55 C56 . . . . -12.1(3) ?
O1 C55 C59 O3 . . . . -178.9(3) ?
C56 C55 C59 O3 . . . . -1.4(4) ?
O1 C55 C59 C60 . . . . -1.5(5) ?
C56 C55 C59 C60 . . . . 175.9(3) ?
C56 C57 C58 O3 . . . . 0.7(5) ?
Cu1 O2 C56 C57 . . . . -170.7(2) ?
Cu1 O2 C56 C55 . . . . 8.5(3) ?
C58 C57 C56 O2 . . . . 175.8(3) ?
C58 C57 C56 C55 . . . . -3.4(4) ?
O1 C55 C56 O2 . . . . 2.0(4) ?
C59 C55 C56 O2 . . . . -175.6(3) ?
O1 C55 C56 C57 . . . . -178.8(3) ?
C59 C55 C56 C57 . . . . 3.7(4) ?
C57 C58 O3 C59 . . . . 1.8(5) ?
C55 C59 O3 C58 . . . . -1.3(4) ?
C60 C59 O3 C58 . . . . -179.0(3) ?
