#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:13:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179682 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/04/7000429.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_7000429
loop_
_publ_author_name
'Johnson, Andrew L.'
'Willcocks, Alexander M.'
'Raithby, Paul R.'
'Warren, Mark R.'
'Kingsley, Andrew J.'
'Odedra, Raj'
_publ_section_title
;
 Unprecedented double migratory insertion of phenyl isocyanide into
 cyclopentadienyl C--H bonds
;
_journal_issue                   6
_journal_name_full               'Dalton Transactions'
_journal_page_first              922
_journal_page_last               924
_journal_paper_doi               10.1039/b822337h
_journal_year                    2009
_chemical_formula_moiety         'C26 H20 Cu N3'
_chemical_formula_sum            'C26 H20 Cu N3'
_chemical_formula_weight         437.99
_chemical_name_common
;Copper(i),(n'n-diphenyl-6-aminofulvene-2-aldimine)(phenyl
isocyanide)
;
_chemical_name_systematic
;
Copper(I),(n'n-diphenyl-6-aminofulvene-2-aldimine)(phenyl isocyanide)
;
_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-97
_cell_angle_alpha                80.536(2)
_cell_angle_beta                 80.213(2)
_cell_angle_gamma                83.978(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1900(4)
_cell_length_b                   10.1970(5)
_cell_length_c                   10.3120(5)
_cell_measurement_reflns_used    10653
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.716
_cell_volume                     1038.26(8)
_computing_cell_refinement       'hkl scalepack (otwinowski & minor 1997)'
_computing_data_collection
'collect, nonius program suite version 1.9 (1997)'
_computing_data_reduction
'denzo and scalepack (otwinowski & minor, 1997)'
_computing_molecular_graphics
'ortep3 for windows - l. j. farrugia, j. appl. crystallogr. 1997, 30, 565'
_computing_publication_material  'shelxtl (sheldrick, 1997)'
_computing_structure_refinement  'shelxl-97 (sheldrick, 1997)'
_computing_structure_solution    'shelxs-97 (sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'nonius kappa ccd'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11479
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         7.86
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0455
_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)+(0.0255P)²+0.2768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3410
_reflns_number_total             4604
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b822337h.txt
_cod_data_source_block           k08alj08
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7000429
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_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
Cu1 Cu 0.45077(3) 0.21044(3) 0.57507(3) 0.02936(12) Uani 1 1 d . . .
N1 N 0.5503(2) 0.3604(2) 0.7628(2) 0.0316(5) Uani 1 1 d . . .
N3 N 0.2733(2) 0.1498(2) 0.5793(2) 0.0268(5) Uani 1 1 d . . .
N2 N 0.5691(2) 0.2035(2) 0.4027(2) 0.0271(5) Uani 1 1 d . . .
C1 C 0.5062(3) 0.2989(3) 0.6964(3) 0.0344(6) Uani 1 1 d . . .
C2 C 0.6130(2) 0.4305(3) 0.8376(2) 0.0280(5) Uani 1 1 d . . .
C3 C 0.6564(3) 0.5547(3) 0.7825(3) 0.0323(6) Uani 1 1 d . . .
H3 H 0.6442 0.5928 0.6945 0.039 Uiso 1 1 calc R . .
C4 C 0.7180(3) 0.6223(3) 0.8587(3) 0.0367(6) Uani 1 1 d . . .
H4 H 0.7465 0.7085 0.8236 0.044 Uiso 1 1 calc R . .
C5 C 0.7381(3) 0.5644(3) 0.9857(3) 0.0379(7) Uani 1 1 d . . .
H5 H 0.7834 0.6098 1.0361 0.045 Uiso 1 1 calc R . .
C6 C 0.6929(3) 0.4412(3) 1.0396(3) 0.0359(6) Uani 1 1 d . . .
H6 H 0.7057 0.4030 1.1275 0.043 Uiso 1 1 calc R . .
C7 C 0.6292(3) 0.3732(3) 0.9664(3) 0.0316(6) Uani 1 1 d . . .
H7 H 0.5969 0.2888 1.0034 0.038 Uiso 1 1 calc R . .
C8 C 0.5496(2) 0.1431(3) 0.3062(2) 0.0266(5) Uani 1 1 d . . .
H8 H 0.6228 0.1405 0.2358 0.032 Uiso 1 1 calc R . .
C9 C 0.4370(2) 0.0807(3) 0.2893(2) 0.0266(5) Uani 1 1 d . . .
C10 C 0.4398(3) 0.0295(3) 0.1696(3) 0.0317(6) Uani 1 1 d . . .
H10 H 0.5143 0.0284 0.1005 0.038 Uiso 1 1 calc R . .
C11 C 0.3176(3) -0.0191(3) 0.1676(3) 0.0329(6) Uani 1 1 d . . .
H11 H 0.2946 -0.0588 0.0982 0.040 Uiso 1 1 calc R . .
C12 C 0.2354(3) 0.0011(3) 0.2857(3) 0.0303(6) Uani 1 1 d . . .
H12 H 0.1460 -0.0229 0.3101 0.036 Uiso 1 1 calc R . .
C13 C 0.3042(3) 0.0629(3) 0.3647(2) 0.0274(5) Uani 1 1 d . . .
C14 C 0.2340(3) 0.0959(3) 0.4867(2) 0.0277(5) Uani 1 1 d . . .
H14 H 0.1432 0.0756 0.5049 0.033 Uiso 1 1 calc R . .
C15 C 0.1720(2) 0.1731(3) 0.6891(2) 0.0273(5) Uani 1 1 d . . .
C16 C 0.0441(3) 0.2291(3) 0.6721(3) 0.0330(6) Uani 1 1 d . . .
H16 H 0.0221 0.2530 0.5850 0.040 Uiso 1 1 calc R . .
C17 C -0.0510(3) 0.2500(3) 0.7808(3) 0.0374(6) Uani 1 1 d . . .
H17 H -0.1372 0.2894 0.7674 0.045 Uiso 1 1 calc R . .
C18 C -0.0223(3) 0.2143(3) 0.9087(3) 0.0396(7) Uani 1 1 d . . .
H18 H -0.0885 0.2273 0.9832 0.047 Uiso 1 1 calc R . .
C19 C 0.1052(3) 0.1590(3) 0.9265(3) 0.0381(6) Uani 1 1 d . . .
H19 H 0.1260 0.1338 1.0140 0.046 Uiso 1 1 calc R . .
C20 C 0.2019(3) 0.1402(3) 0.8185(3) 0.0323(6) Uani 1 1 d . . .
H20 H 0.2893 0.1047 0.8321 0.039 Uiso 1 1 calc R . .
C21 C 0.6936(2) 0.2644(3) 0.3814(2) 0.0270(5) Uani 1 1 d . . .
C22 C 0.8141(3) 0.2031(3) 0.3263(2) 0.0301(6) Uani 1 1 d . . .
H22 H 0.8170 0.1155 0.3051 0.036 Uiso 1 1 calc R . .
C23 C 0.9298(3) 0.2695(3) 0.3022(3) 0.0366(6) Uani 1 1 d . . .
H23 H 1.0112 0.2276 0.2631 0.044 Uiso 1 1 calc R . .
C24 C 0.9279(3) 0.3962(3) 0.3344(3) 0.0414(7) Uani 1 1 d . . .
H24 H 1.0075 0.4413 0.3179 0.050 Uiso 1 1 calc R . .
C25 C 0.8089(3) 0.4564(3) 0.3908(3) 0.0394(7) Uani 1 1 d . . .
H25 H 0.8066 0.5434 0.4133 0.047 Uiso 1 1 calc R . .
C26 C 0.6923(3) 0.3907(3) 0.4149(3) 0.0332(6) Uani 1 1 d . . .
H26 H 0.6112 0.4327 0.4546 0.040 Uiso 1 1 calc R . .
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'
Cu Cu 0.3201 1.2651 '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'
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
C1 Cu1 N3 128.01(10) . . ?
C1 Cu1 N2 117.50(11) . . ?
N3 Cu1 N2 113.41(8) . . ?
C1 N1 C2 175.6(3) . . ?
C14 N3 C15 115.2(2) . . ?
C14 N3 Cu1 126.61(17) . . ?
C15 N3 Cu1 118.04(16) . . ?
C8 N2 C21 115.1(2) . . ?
C8 N2 Cu1 126.72(18) . . ?
C21 N2 Cu1 118.08(16) . . ?
N1 C1 Cu1 173.3(2) . . ?
C3 C2 C7 121.7(2) . . ?
C3 C2 N1 119.6(2) . . ?
C7 C2 N1 118.7(2) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
N2 C8 C9 130.5(2) . . ?
N2 C8 H8 114.7 . . ?
C9 C8 H8 114.7 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 C13 106.2(2) . . ?
C8 C9 C13 135.0(2) . . ?
C11 C10 C9 110.2(2) . . ?
C11 C10 H10 124.9 . . ?
C9 C10 H10 124.9 . . ?
C12 C11 C10 107.4(2) . . ?
C12 C11 H11 126.3 . . ?
C10 C11 H11 126.3 . . ?
C11 C12 C13 110.2(2) . . ?
C11 C12 H12 124.9 . . ?
C13 C12 H12 124.9 . . ?
C14 C13 C12 118.0(2) . . ?
C14 C13 C9 135.8(2) . . ?
C12 C13 C9 106.1(2) . . ?
N3 C14 C13 130.8(2) . . ?
N3 C14 H14 114.6 . . ?
C13 C14 H14 114.6 . . ?
C16 C15 C20 118.4(2) . . ?
C16 C15 N3 122.3(2) . . ?
C20 C15 N3 119.2(2) . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C15 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C26 C21 C22 119.0(2) . . ?
C26 C21 N2 118.1(2) . . ?
C22 C21 N2 122.9(2) . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.1(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 120.5(3) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.5(3) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
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 C1 1.849(3) . ?
Cu1 N3 1.964(2) . ?
Cu1 N2 1.978(2) . ?
N1 C1 1.170(3) . ?
N1 C2 1.399(3) . ?
N3 C14 1.312(3) . ?
N3 C15 1.430(3) . ?
N2 C8 1.306(3) . ?
N2 C21 1.439(3) . ?
C2 C3 1.385(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.417(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(4) . ?
C9 C13 1.455(4) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 C20 1.397(4) . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.385(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Cu1 N3 C14 174.6(2) . . . . ?
N2 Cu1 N3 C14 6.9(2) . . . . ?
C1 Cu1 N3 C15 -1.1(2) . . . . ?
N2 Cu1 N3 C15 -168.80(16) . . . . ?
C1 Cu1 N2 C8 177.95(19) . . . . ?
N3 Cu1 N2 C8 -12.9(2) . . . . ?
C1 Cu1 N2 C21 1.6(2) . . . . ?
N3 Cu1 N2 C21 170.69(16) . . . . ?
C7 C2 C3 C4 0.3(4) . . . . ?
N1 C2 C3 C4 179.9(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C3 C2 C7 C6 -1.5(4) . . . . ?
N1 C2 C7 C6 178.9(2) . . . . ?
C21 N2 C8 C9 -175.5(2) . . . . ?
Cu1 N2 C8 C9 8.0(4) . . . . ?
N2 C8 C9 C10 176.0(2) . . . . ?
N2 C8 C9 C13 2.3(5) . . . . ?
C8 C9 C10 C11 -175.8(2) . . . . ?
C13 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 177.6(2) . . . . ?
C11 C12 C13 C9 -0.2(3) . . . . ?
C10 C9 C13 C14 -176.9(3) . . . . ?
C8 C9 C13 C14 -2.6(5) . . . . ?
C10 C9 C13 C12 0.4(3) . . . . ?
C8 C9 C13 C12 174.7(3) . . . . ?
C15 N3 C14 C13 177.9(2) . . . . ?
Cu1 N3 C14 C13 2.1(4) . . . . ?
C12 C13 C14 N3 178.2(2) . . . . ?
C9 C13 C14 N3 -4.8(5) . . . . ?
C14 N3 C15 C16 -44.7(3) . . . . ?
Cu1 N3 C15 C16 131.5(2) . . . . ?
C14 N3 C15 C20 135.9(3) . . . . ?
Cu1 N3 C15 C20 -47.9(3) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
N3 C15 C16 C17 179.9(3) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C19 C20 C15 -1.8(4) . . . . ?
C16 C15 C20 C19 2.0(4) . . . . ?
N3 C15 C20 C19 -178.6(2) . . . . ?
C8 N2 C21 C26 136.9(2) . . . . ?
Cu1 N2 C21 C26 -46.3(3) . . . . ?
C8 N2 C21 C22 -41.8(3) . . . . ?
Cu1 N2 C21 C22 135.0(2) . . . . ?
C26 C21 C22 C23 -1.8(4) . . . . ?
N2 C21 C22 C23 176.9(2) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
N2 C21 C26 C25 -177.1(2) . . . . ?
C24 C25 C26 C21 -0.6(4) . . . . ?
