#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/04/7110408.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7110408
loop_
_publ_author_name
'Taillefer, Marc'
'Inguimbert, Nicolas'
'Cristau, Henri-Jean'
'Jäger, Lothar'
'Merzweiler, Kurt'
_publ_section_title
;
 Synthesis of the sodium diphenylbis(cyanamido)phosphonium diylide by a
 new variation of the Staudinger reaction
;
_journal_issue                   6
_journal_name_full               'Chemical Communications'
_journal_page_first              565
_journal_paper_doi               10.1039/a808641i
_journal_year                    1999
_chemical_compound_source        turqoise
_chemical_formula_sum            'C38 H30 Cu N10 P2'
_chemical_formula_weight         752.20
_chemical_melting_point          465.15
_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
_audit_creation_method           SHELXL
_cell_angle_alpha                107.588(8)
_cell_angle_beta                 91.823(11)
_cell_angle_gamma                98.651(11)
_cell_formula_units_Z            2
_cell_length_a                   8.4325(14)
_cell_length_b                   13.5423(12)
_cell_length_c                   16.555(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1775.6(4)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10554
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.749
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             774
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_obs   1.106
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         6478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_restrained_S_obs      1.106
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_obs          0.0479
_refine_ls_shift/esd_max         -0.009
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0787P)²+0.0554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1330
_refine_ls_wR_factor_obs         0.1186
_reflns_number_observed          4688
_reflns_number_total             6478
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            808641isup1.cif
_cod_data_source_block           ipds3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '192 C' was changed to '465.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.0554P] 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^)+(0.0787P)^2^+0.0554P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1775.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7110408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.2882(5) 0.1288(3) 1.2589(2) 0.0602(10) Uani 1 d
C2 C 0.0980(4) 0.1321(3) 1.1263(2) 0.0501(8) Uani 1 d
C3 C 0.3528(4) 0.2915(3) 0.8430(2) 0.0463(8) Uani 1 d
C4 C 0.6292(4) 0.5325(3) 0.8270(2) 0.0470(8) Uani 1 d
C5 C 0.0821(4) 0.2119(3) 1.3364(2) 0.0493(8) Uani 1 d
C6 C 0.0051(6) 0.2514(3) 1.4092(3) 0.0645(10) Uani 1 d
H1 H -0.0924(52) 0.2093(33) 1.4165(25) 0.067(12) Uiso 1 d
C7 C 0.0739(7) 0.3438(4) 1.4711(3) 0.0788(13) Uani 1 d
H2 H 0.0205(65) 0.3613(42) 1.5183(35) 0.106(18) Uiso 1 d
C8 C 0.2180(7) 0.3975(4) 1.4613(3) 0.0816(14) Uani 1 d
H3 H 0.2751(54) 0.4556(37) 1.5070(28) 0.079(13) Uiso 1 d
C9 C 0.2959(6) 0.3598(4) 1.3892(3) 0.0786(13) Uani 1 d
H4 H 0.4004(62) 0.3999(40) 1.3887(30) 0.094(16) Uiso 1 d
C10 C 0.2300(5) 0.2675(3) 1.3273(3) 0.0624(10) Uani 1 d
H5 H 0.2906(56) 0.2372(36) 1.2789(29) 0.087(14) Uiso 1 d
C11 C 0.0682(5) -0.0091(3) 1.3023(2) 0.0501(8) Uani 1 d
C12 C -0.0138(5) -0.0416(3) 1.3631(3) 0.0605(10) Uani 1 d
H6 H -0.1218(47) -0.0073(30) 1.3862(24) 0.064(11) Uiso 1 d
C13 C 0.0495(6) -0.1068(4) 1.4014(3) 0.0688(12) Uani 1 d
H7 H -0.0003(55) -0.1259(37) 1.4357(29) 0.079(15) Uiso 1 d
C14 C 0.1889(6) -0.1422(3) 1.3771(3) 0.0698(12) Uani 1 d
H8 H 0.2241(58) -0.1885(39) 1.4050(29) 0.093(15) Uiso 1 d
C15 C 0.2704(6) -0.1112(4) 1.3162(3) 0.0744(12) Uani 1 d
H9 H 0.3751(56) -0.1395(37) 1.3001(28) 0.087(14) Uiso 1 d
C16 C 0.2107(6) -0.0444(3) 1.2793(3) 0.0661(11) Uani 1 d
H10 H 0.2644(46) -0.0231(30) 1.2359(25) 0.063(11) Uiso 1 d
C17 C -0.0310(5) 0.3870(3) 1.0587(3) 0.0582(9) Uani 1 d
H11 H 0.0141(55) 0.4008(35) 1.1046(28) 0.074(14) Uiso 1 d
C18 C -0.1661(5) 0.4295(4) 1.0520(3) 0.0693(11) Uani 1 d
H12 H -0.1997(63) 0.4803(42) 1.1037(34) 0.111(18) Uiso 1 d
C19 C -0.2566(5) 0.3968(4) 0.9757(3) 0.0695(11) Uani 1 d
H13 H -0.3395(54) 0.4323(35) 0.9657(27) 0.078(13) Uiso 1 d
C20 C -0.2063(5) 0.3231(4) 0.9087(3) 0.0692(11) Uani 1 d
H14 H -0.2617(54) 0.3060(35) 0.8581(28) 0.079(13) Uiso 1 d
C21 C -0.0682(5) 0.2854(3) 0.9203(2) 0.0574(9) Uani 1 d
H15 H -0.0303(43) 0.2399(29) 0.8714(24) 0.056(10) Uiso 1 d
C22 C 0.4329(5) 0.1051(3) 0.9301(2) 0.0555(9) Uani 1 d
H16 H 0.3464(46) 0.0941(29) 0.8828(24) 0.059(11) Uiso 1 d
C23 C 0.5647(5) 0.0563(3) 0.9185(3) 0.0649(11) Uani 1 d
H17 H 0.5708(49) 0.0033(34) 0.8665(27) 0.073(12) Uiso 1 d
C24 C 0.6888(5) 0.0883(3) 0.9816(3) 0.0669(12) Uani 1 d
H18 H 0.7881(58) 0.0560(37) 0.9727(29) 0.097(16) Uiso 1 d
C25 C 0.6745(5) 0.1656(4) 1.0542(3) 0.0634(10) Uani 1 d
H19 H 0.7446(54) 0.1868(35) 1.0969(28) 0.072(14) Uiso 1 d
C26 C 0.5370(5) 0.2097(3) 1.0631(2) 0.0533(8) Uani 1 d
H20 H 0.5256(42) 0.2638(29) 1.1125(23) 0.052(10) Uiso 1 d
C27 C 0.2755(4) 0.4296(2) 0.7219(2) 0.0385(7) Uani 1 d
C28 C 0.1223(4) 0.3736(3) 0.7225(2) 0.0468(8) Uani 1 d
H21 H 0.1125(38) 0.3065(27) 0.7270(20) 0.040(9) Uiso 1 d
C29 C -0.0133(4) 0.4173(3) 0.7174(2) 0.0585(9) Uani 1 d
H22 H -0.1154(54) 0.3726(35) 0.7167(27) 0.078(13) Uiso 1 d
C30 C 0.0008(5) 0.5164(4) 0.7121(2) 0.0636(11) Uani 1 d
H23 H -0.0874(49) 0.5517(32) 0.7105(24) 0.069(12) Uiso 1 d
C31 C 0.1509(6) 0.5744(4) 0.7116(3) 0.0672(11) Uani 1 d
H24 H 0.1684(54) 0.6398(38) 0.7066(28) 0.082(14) Uiso 1 d
C32 C 0.2878(5) 0.5306(3) 0.7169(2) 0.0526(8) Uani 1 d
H25 H 0.3856(44) 0.5704(28) 0.7180(21) 0.049(10) Uiso 1 d
C33 C 0.4798(4) 0.2952(3) 0.6185(2) 0.0391(7) Uani 1 d
C34 C 0.3949(5) 0.1956(3) 0.5846(2) 0.0596(10) Uani 1 d
H26 H 0.3355(54) 0.1636(35) 0.6176(27) 0.080(14) Uiso 1 d
C35 C 0.4098(6) 0.1373(4) 0.5012(3) 0.0785(14) Uani 1 d
H27 H 0.3456(67) 0.0705(46) 0.4768(34) 0.114(18) Uiso 1 d
C36 C 0.5082(6) 0.1803(4) 0.4524(3) 0.0760(13) Uani 1 d
H28 H 0.5156(55) 0.1393(38) 0.3960(30) 0.088(14) Uiso 1 d
C37 C 0.5926(5) 0.2796(4) 0.4855(2) 0.0648(11) Uani 1 d
H29 H 0.6740(54) 0.3148(35) 0.4485(28) 0.086(14) Uiso 1 d
C38 C 0.5799(4) 0.3383(3) 0.5687(2) 0.0500(8) Uani 1 d
H30 H 0.6368(50) 0.4089(35) 0.5910(25) 0.073(13) Uiso 1 d
N1 N -0.1939(4) 0.0630(3) 1.2609(2) 0.0712(9) Uani 1 d
N2 N -0.3839(5) 0.1826(4) 1.2574(2) 0.0862(12) Uani 1 d
N3 N 0.0776(5) 0.0710(3) 1.1728(2) 0.0733(10) Uani 1 d
N4 N 0.1222(4) 0.1783(3) 1.0797(2) 0.0620(8) Uani 1 d
N5 N 0.4203(4) 0.2845(2) 0.7737(2) 0.0551(8) Uani 1 d
N6 N 0.2932(4) 0.2900(3) 0.9041(2) 0.0622(8) Uani 1 d
N7 N 0.6069(3) 0.4585(2) 0.7549(2) 0.0538(7) Uani 1 d
N8 N 0.6590(4) 0.6005(3) 0.8893(2) 0.0621(8) Uani 1 d
N9 N 0.4181(3) 0.1830(2) 1.0020(2) 0.0459(6) Uani 1 d
N10 N 0.0208(3) 0.3167(2) 0.9947(2) 0.0433(6) Uani 1 d
P1 P -0.00163(12) 0.08652(8) 1.26143(6) 0.0501(2) Uani 1 d
P2 P 0.45055(9) 0.37006(7) 0.72480(5) 0.0374(2) Uani 1 d
Cu Cu 0.22761(5) 0.26020(3) 1.00891(2) 0.04088(14) Uani 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'
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
_geom_angle_site_symmetry_3
N2 C1 N1 174.6(5) .
N4 C2 N3 173.2(4) .
N6 C3 N5 174.9(4) .
N8 C4 N7 175.3(4) .
C6 C5 C10 118.2(4) .
C6 C5 P1 119.6(3) .
C10 C5 P1 121.9(3) .
C5 C6 C7 120.7(5) .
C8 C7 C6 120.4(5) .
C7 C8 C9 119.7(5) .
C8 C9 C10 120.6(5) .
C9 C10 C5 120.3(4) .
C12 C11 C16 119.1(3) .
C12 C11 P1 119.7(3) .
C16 C11 P1 121.0(3) .
C11 C12 C13 119.7(4) .
C14 C13 C12 120.4(4) .
C13 C14 C15 120.2(4) .
C14 C15 C16 119.8(4) .
C15 C16 C11 120.7(4) .
N10 C17 C18 123.9(4) .
C17 C18 C19 118.8(4) .
C18 C19 C20 118.3(4) .
C21 C20 C19 119.3(4) .
N10 C21 C20 122.8(4) .
N9 C22 C23 122.6(4) .
C22 C23 C24 118.9(4) .
C25 C24 C23 118.9(4) .
C24 C25 C26 119.4(4) .
N9 C26 C25 122.9(4) .
C32 C27 C28 118.4(3) .
C32 C27 P2 121.1(3) .
C28 C27 P2 120.5(2) .
C29 C28 C27 120.9(3) .
C30 C29 C28 119.9(4) .
C29 C30 C31 120.8(4) .
C32 C31 C30 119.4(4) .
C27 C32 C31 120.5(4) .
C34 C33 C38 119.6(3) .
C34 C33 P2 119.2(2) .
C38 C33 P2 121.2(3) .
C33 C34 C35 120.5(4) .
C36 C35 C34 119.6(4) .
C37 C36 C35 120.2(4) .
C36 C37 C38 120.8(4) .
C37 C38 C33 119.3(4) .
C1 N1 P1 124.9(3) .
C2 N3 P1 130.4(3) .
C2 N4 Cu 164.1(3) .
C3 N5 P2 128.4(3) .
C3 N6 Cu 165.0(3) .
C4 N7 P2 124.7(2) .
C4 N8 Cu 164.7(3) 2_667
C26 N9 C22 117.1(3) .
C26 N9 Cu 123.1(2) .
C22 N9 Cu 119.7(3) .
C17 N10 C21 116.9(3) .
C17 N10 Cu 121.5(2) .
C21 N10 Cu 121.6(2) .
N3 P1 N1 118.9(2) .
N3 P1 C11 104.0(2) .
N1 P1 C11 104.9(2) .
N3 P1 C5 110.7(2) .
N1 P1 C5 111.6(2) .
C11 P1 C5 105.4(2) .
N7 P2 N5 117.9(2) .
N7 P2 C27 110.0(2) .
N5 P2 C27 110.40(14) .
N7 P2 C33 105.18(15) .
N5 P2 C33 104.1(2) .
C27 P2 C33 108.54(14) .
N6 Cu N4 157.4(2) .
N6 Cu N9 86.99(12) .
N4 Cu N9 90.06(12) .
N6 Cu N10 88.11(11) .
N4 Cu N10 90.80(11) .
N9 Cu N10 169.26(11) .
N6 Cu N8 104.02(14) 2_667
N4 Cu N8 98.60(14) 2_667
N9 Cu N8 95.42(12) 2_667
N10 Cu N8 95.04(11) 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.170(5) .
C1 N1 1.287(5) .
C2 N4 1.136(4) .
C2 N3 1.288(4) .
C3 N6 1.148(4) .
C3 N5 1.282(4) .
C4 N8 1.148(4) .
C4 N7 1.293(4) .
C5 C6 1.387(5) .
C5 C10 1.393(5) .
C5 P1 1.798(4) .
C6 C7 1.387(7) .
C7 C8 1.360(8) .
C8 C9 1.379(7) .
C9 C10 1.378(7) .
C11 C12 1.381(5) .
C11 C16 1.381(5) .
C11 P1 1.793(3) .
C12 C13 1.388(6) .
C13 C14 1.362(7) .
C14 C15 1.370(7) .
C15 C16 1.377(6) .
C17 N10 1.328(5) .
C17 C18 1.367(6) .
C18 C19 1.369(6) .
C19 C20 1.376(6) .
C20 C21 1.370(6) .
C21 N10 1.337(4) .
C22 N9 1.355(4) .
C22 C23 1.367(6) .
C23 C24 1.376(6) .
C24 C25 1.358(6) .
C25 C26 1.374(5) .
C26 N9 1.328(5) .
C27 C32 1.385(5) .
C27 C28 1.397(5) .
C27 P2 1.791(3) .
C28 C29 1.376(5) .
C29 C30 1.358(6) .
C30 C31 1.388(6) .
C31 C32 1.387(5) .
C33 C34 1.369(5) .
C33 C38 1.385(4) .
C33 P2 1.792(3) .
C34 C35 1.388(5) .
C35 C36 1.365(7) .
C36 C37 1.362(7) .
C37 C38 1.384(5) .
N1 P1 1.604(4) .
N3 P1 1.601(3) .
N4 Cu 1.987(3) .
N5 P2 1.597(3) .
N6 Cu 1.974(3) .
N7 P2 1.595(3) .
N8 Cu 2.178(3) 2_667
N9 Cu 2.032(3) .
N10 Cu 2.042(3) .
Cu N8 2.178(3) 2_667
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183708
