#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/67/4326749.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_4326749
loop_
_publ_author_name
'Ting Zhu'
'Truman C. Wambach'
'Michael D. Fryzuk'
_publ_contact_author_email       fryzuk@chem.ubc.ca
_publ_contact_author_name        'Michael D. Fryzuk'
_publ_section_title
;
 New Cyclopentenyl-Linked [NPN] Ligands and Their Coordination Chemistry
 with Zirconium: Synthesis of a Dinuclear Side-On-Bound Dinitrogen Complex
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11212
_journal_page_last               11221
_journal_paper_doi               10.1021/ic201762r
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         ' C32 H35 Cl2 N2 P Zr, 2(C3 H3)'
_chemical_formula_sum            'C38 H41 Cl2 N2 P Zr'
_chemical_formula_weight         718.86
_chemical_name_common            Cy5[NPN]DMPZrCl2
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ac'
_symmetry_space_group_name_H-M   'P c m n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.976(4)
_cell_length_b                   14.267(5)
_cell_length_c                   19.098(7)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.890
_cell_measurement_theta_min      2.375
_cell_volume                     3536(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46631
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    .536
_exptl_absorpt_correction_T_max  0.8346
_exptl_absorpt_correction_T_min  0.8142
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0216
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0302P)²+1.5396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                3953
_reflns_number_total             4392
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic201762r_si_002_2.cif
_cod_data_source_block           mf770_0m
_cod_original_formula_sum        ' C38 H41 Cl2 N2 P Zr'
_cod_database_code               4326749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x, -y-1/2, 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
Zr1 Zr 0.136884(12) 0.2500 0.101139(8) 0.01827(5) Uani 1 2 d S
Cl1 Cl -0.04623(3) 0.2500 0.11397(3) 0.03356(11) Uani 1 2 d S
P1 P 0.14541(3) 0.2500 0.24600(2) 0.01795(9) Uani 1 2 d S
Cl2 Cl 0.15268(5) 0.2500 -0.02453(2) 0.03787(12) Uani 1 2 d S
N1 N 0.20408(7) 0.37660(7) 0.13086(5) 0.02051(19) Uani 1 1 d .
C2 C 0.21901(9) 0.35340(8) 0.25695(6) 0.0207(2) Uani 1 1 d .
C6 C 0.21020(9) 0.44872(8) 0.07758(6) 0.0219(2) Uani 1 1 d .
C11 C 0.29569(10) 0.45282(9) 0.03302(6) 0.0275(3) Uani 1 1 d .
C5 C 0.29939(11) 0.48992(9) 0.21331(7) 0.0299(3) Uani 1 1 d .
H9A H 0.2715 0.5443 0.1894 0.036 Uiso 1 1 calc R
H9B H 0.3709 0.4817 0.2000 0.036 Uiso 1 1 calc R
C14 C 0.04716(13) 0.2500 0.31342(8) 0.0215(3) Uani 1 2 d S
C1 C 0.23681(9) 0.40294(8) 0.19787(6) 0.0205(2) Uani 1 1 d .
C7 C 0.12981(10) 0.51372(9) 0.07202(7) 0.0287(3) Uani 1 1 d .
C10 C 0.29722(12) 0.52235(11) -0.01839(7) 0.0371(3) Uani 1 1 d .
H13 H 0.3529 0.5258 -0.0489 0.045 Uiso 1 1 calc R
C3 C 0.27033(11) 0.39826(9) 0.31961(6) 0.0283(3) Uani 1 1 d .
H14A H 0.3349 0.3676 0.3309 0.034 Uiso 1 1 calc R
H14B H 0.2257 0.3973 0.3604 0.034 Uiso 1 1 calc R
C15 C 0.00779(10) 0.16570(10) 0.33879(7) 0.0287(3) Uani 1 1 d .
H15 H 0.0323 0.1091 0.3213 0.034 Uiso 1 1 calc R
C16 C -0.06799(11) 0.16602(11) 0.39008(7) 0.0352(3) Uani 1 1 d .
H16 H -0.0938 0.1096 0.4071 0.042 Uiso 1 1 calc R
C17 C -0.10529(15) 0.2500 0.41602(10) 0.0365(5) Uani 1 2 d S
H17 H -0.1554 0.2500 0.4509 0.044 Uiso 1 2 calc SR
C8 C 0.13547(13) 0.58200(11) 0.02003(8) 0.0401(3) Uani 1 1 d .
H18 H 0.0826 0.6256 0.0156 0.048 Uiso 1 1 calc R
C9 C 0.21804(14) 0.58579(11) -0.02478(7) 0.0430(4) Uani 1 1 d .
H19 H 0.2204 0.6314 -0.0595 0.052 Uiso 1 1 calc R
C4 C 0.28785(12) 0.49889(10) 0.29306(7) 0.0345(3) Uani 1 1 d .
H20A H 0.2296 0.5386 0.3048 0.041 Uiso 1 1 calc R
H20B H 0.3496 0.5255 0.3136 0.041 Uiso 1 1 calc R
C13 C 0.38407(12) 0.38601(12) 0.03976(9) 0.0431(4) Uani 1 1 d .
H21A H 0.3717 0.3321 0.0109 0.065 Uiso 1 1 calc R
H21B H 0.3907 0.3668 0.0877 0.065 Uiso 1 1 calc R
H21C H 0.4464 0.4163 0.0250 0.065 Uiso 1 1 calc R
C18 C 0.5055(2) 0.2500 0.23020(19) 0.0667(8) Uani 1 2 d S
H22 H 0.4351 0.2500 0.2212 0.080 Uiso 1 2 calc SR
C20 C 0.6442(2) 0.2500 0.31139(15) 0.0547(6) Uani 1 2 d S
H23 H 0.6676 0.2500 0.3574 0.066 Uiso 1 2 calc SR
C22 C 0.6797(2) 0.2500 0.18940(14) 0.0487(6) Uani 1 2 d S
H24 H 0.7269 0.2500 0.1528 0.058 Uiso 1 2 calc SR
C19 C 0.5406(2) 0.2500 0.29784(17) 0.0577(7) Uani 1 2 d S
H25 H 0.4938 0.2500 0.3347 0.069 Uiso 1 2 calc SR
C21 C 0.71355(19) 0.2500 0.25731(14) 0.0481(6) Uani 1 2 d S
H26 H 0.7839 0.2500 0.2667 0.058 Uiso 1 2 calc SR
C23 C 0.5749(2) 0.2500 0.17529(16) 0.0619(7) Uani 1 2 d S
H27 H 0.5515 0.2500 0.1293 0.074 Uiso 1 2 calc SR
C12 C 0.03962(11) 0.51169(11) 0.12131(9) 0.0407(3) Uani 1 1 d .
H28A H 0.0622 0.5283 0.1675 0.061 Uiso 1 1 calc R
H28B H 0.0105 0.4498 0.1221 0.061 Uiso 1 1 calc R
H28C H -0.0116 0.5556 0.1058 0.061 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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
N1 Zr1 N1 120.12(6) . 8_565
N1 Zr1 Cl1 112.84(3) . .
N1 Zr1 Cl1 112.84(3) 8_565 .
N1 Zr1 Cl2 103.63(3) . .
N1 Zr1 Cl2 103.63(3) 8_565 .
Cl1 Zr1 Cl2 100.771(19) . .
N1 Zr1 P1 73.22(3) . .
N1 Zr1 P1 73.22(3) 8_565 .
Cl1 Zr1 P1 86.401(16) . .
Cl2 Zr1 P1 172.828(18) . .
C2 P1 C2 112.94(8) . 8_565
C2 P1 C14 107.20(5) . .
C2 P1 C14 107.20(5) 8_565 .
C2 P1 Zr1 98.02(4) . .
C2 P1 Zr1 98.02(4) 8_565 .
C14 P1 Zr1 132.99(6) . .
C1 N1 C6 115.76(10) . .
C1 N1 Zr1 127.48(7) . .
C6 N1 Zr1 116.56(7) . .
C1 C2 C3 111.36(11) . .
C1 C2 P1 115.45(9) . .
C3 C2 P1 133.16(9) . .
C11 C6 C7 121.13(12) . .
C11 C6 N1 120.01(11) . .
C7 C6 N1 118.87(11) . .
C10 C11 C6 117.95(13) . .
C10 C11 C13 120.15(13) . .
C6 C11 C13 121.90(12) . .
C1 C5 C4 102.08(10) . .
C1 C5 H9A 111.4 . .
C4 C5 H9A 111.4 . .
C1 C5 H9B 111.4 . .
C4 C5 H9B 111.4 . .
H9A C5 H9B 109.2 . .
C15 C14 C15 119.30(16) 8_565 .
C15 C14 P1 120.33(8) 8_565 .
C15 C14 P1 120.33(8) . .
C2 C1 N1 124.83(11) . .
C2 C1 C5 111.00(10) . .
N1 C1 C5 124.16(10) . .
C8 C7 C6 118.56(13) . .
C8 C7 C12 120.08(13) . .
C6 C7 C12 121.35(12) . .
C9 C10 C11 121.32(13) . .
C9 C10 H13 119.3 . .
C11 C10 H13 119.3 . .
C2 C3 C4 101.48(10) . .
C2 C3 H14A 111.5 . .
C4 C3 H14A 111.5 . .
C2 C3 H14B 111.5 . .
C4 C3 H14B 111.5 . .
H14A C3 H14B 109.3 . .
C16 C15 C14 120.15(13) . .
C16 C15 H15 119.9 . .
C14 C15 H15 119.9 . .
C17 C16 C15 120.21(14) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C16 119.94(17) 8_565 .
C16 C17 H17 120.0 8_565 .
C16 C17 H17 120.0 . .
C9 C8 C7 120.88(14) . .
C9 C8 H18 119.6 . .
C7 C8 H18 119.6 . .
C8 C9 C10 120.14(13) . .
C8 C9 H19 119.9 . .
C10 C9 H19 119.9 . .
C5 C4 C3 105.27(10) . .
C5 C4 H20A 110.7 . .
C3 C4 H20A 110.7 . .
C5 C4 H20B 110.7 . .
C3 C4 H20B 110.7 . .
H20A C4 H20B 108.8 . .
C11 C13 H21A 109.5 . .
C11 C13 H21B 109.5 . .
H21A C13 H21B 109.5 . .
C11 C13 H21C 109.5 . .
H21A C13 H21C 109.5 . .
H21B C13 H21C 109.5 . .
C19 C18 C23 119.9(3) . .
C19 C18 H22 120.0 . .
C23 C18 H22 120.0 . .
C19 C20 C21 120.2(3) . .
C19 C20 H23 119.9 . .
C21 C20 H23 119.9 . .
C21 C22 C23 119.9(2) . .
C21 C22 H24 120.0 . .
C23 C22 H24 120.0 . .
C20 C19 C18 120.3(3) . .
C20 C19 H25 119.8 . .
C18 C19 H25 119.8 . .
C22 C21 C20 120.2(2) . .
C22 C21 H26 119.9 . .
C20 C21 H26 119.9 . .
C18 C23 C22 119.5(3) . .
C18 C23 H27 120.3 . .
C22 C23 H27 120.3 . .
C7 C12 H28A 109.5 . .
C7 C12 H28B 109.5 . .
H28A C12 H28B 109.5 . .
C7 C12 H28C 109.5 . .
H28A C12 H28C 109.5 . .
H28B C12 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zr1 N1 2.0845(11) .
Zr1 N1 2.0845(11) 8_565
Zr1 Cl1 2.3887(9) .
Zr1 Cl2 2.4088(10) .
Zr1 P1 2.7688(11) .
P1 C2 1.7698(13) .
P1 C2 1.7698(12) 8_565
P1 C14 1.8119(17) .
N1 C1 1.3999(15) .
N1 C6 1.4492(15) .
C2 C1 1.3512(16) .
C2 C3 1.5117(16) .
C6 C11 1.3995(17) .
C6 C7 1.3998(18) .
C11 C10 1.3958(19) .
C11 C13 1.497(2) .
C5 C1 1.5121(17) .
C5 C4 1.5358(19) .
C5 H9A 0.9700 .
C5 H9B 0.9700 .
C14 C15 1.3937(16) 8_565
C14 C15 1.3937(16) .
C7 C8 1.393(2) .
C7 C12 1.502(2) .
C10 C9 1.375(2) .
C10 H13 0.9300 .
C3 C4 1.5395(19) .
C3 H14A 0.9700 .
C3 H14B 0.9700 .
C15 C16 1.3878(18) .
C15 H15 0.9300 .
C16 C17 1.3840(19) .
C16 H16 0.9300 .
C17 C16 1.3840(19) 8_565
C17 H17 0.9300 .
C8 C9 1.372(2) .
C8 H18 0.9300 .
C9 H19 0.9300 .
C4 H20A 0.9700 .
C4 H20B 0.9700 .
C13 H21A 0.9600 .
C13 H21B 0.9600 .
C13 H21C 0.9600 .
C18 C19 1.370(4) .
C18 C23 1.383(4) .
C18 H22 0.9300 .
C20 C19 1.369(4) .
C20 C21 1.370(4) .
C20 H23 0.9300 .
C22 C21 1.369(4) .
C22 C23 1.385(4) .
C22 H24 0.9300 .
C19 H25 0.9300 .
C21 H26 0.9300 .
C23 H27 0.9300 .
C12 H28A 0.9600 .
C12 H28B 0.9600 .
C12 H28C 0.9600 .
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_4
N1 Zr1 P1 C2 -7.50(5) . .
N1 Zr1 P1 C2 122.17(5) 8_565 .
Cl1 Zr1 P1 C2 -122.67(4) . .
Cl2 Zr1 P1 C2 57.33(4) . .
N1 Zr1 P1 C2 -122.17(5) . 8_565
N1 Zr1 P1 C2 7.50(5) 8_565 8_565
Cl1 Zr1 P1 C2 122.67(4) . 8_565
Cl2 Zr1 P1 C2 -57.33(4) . 8_565
N1 Zr1 P1 C14 115.16(3) . .
N1 Zr1 P1 C14 -115.16(3) 8_565 .
Cl1 Zr1 P1 C14 0.0 . .
Cl2 Zr1 P1 C14 180.0 . .
N1 Zr1 N1 C1 -49.20(12) 8_565 .
Cl1 Zr1 N1 C1 87.79(10) . .
Cl2 Zr1 N1 C1 -164.10(9) . .
P1 Zr1 N1 C1 9.22(9) . .
N1 Zr1 N1 C6 136.28(7) 8_565 .
Cl1 Zr1 N1 C6 -86.73(8) . .
Cl2 Zr1 N1 C6 21.37(8) . .
P1 Zr1 N1 C6 -165.30(8) . .
C2 P1 C2 C1 109.30(9) 8_565 .
C14 P1 C2 C1 -132.84(10) . .
Zr1 P1 C2 C1 7.03(10) . .
C2 P1 C2 C3 -68.62(15) 8_565 .
C14 P1 C2 C3 49.24(14) . .
Zr1 P1 C2 C3 -170.90(12) . .
C1 N1 C6 C11 96.40(13) . .
Zr1 N1 C6 C11 -88.42(12) . .
C1 N1 C6 C7 -83.29(14) . .
Zr1 N1 C6 C7 91.89(12) . .
C7 C6 C11 C10 -1.58(18) . .
N1 C6 C11 C10 178.74(11) . .
C7 C6 C11 C13 177.86(13) . .
N1 C6 C11 C13 -1.82(18) . .
C2 P1 C14 C15 30.28(15) . 8_565
C2 P1 C14 C15 151.82(12) 8_565 8_565
Zr1 P1 C14 C15 -88.95(13) . 8_565
C2 P1 C14 C15 -151.82(12) . .
C2 P1 C14 C15 -30.28(15) 8_565 .
Zr1 P1 C14 C15 88.95(13) . .
C3 C2 C1 N1 176.50(11) . .
P1 C2 C1 N1 -1.88(16) . .
C3 C2 C1 C5 -2.08(15) . .
P1 C2 C1 C5 179.55(9) . .
C6 N1 C1 C2 166.46(11) . .
Zr1 N1 C1 C2 -8.10(17) . .
C6 N1 C1 C5 -15.15(16) . .
Zr1 N1 C1 C5 170.29(9) . .
C4 C5 C1 C2 -16.31(14) . .
C4 C5 C1 N1 165.11(11) . .
C11 C6 C7 C8 1.25(19) . .
N1 C6 C7 C8 -179.06(12) . .
C11 C6 C7 C12 -177.86(12) . .
N1 C6 C7 C12 1.82(18) . .
C6 C11 C10 C9 0.79(19) . .
C13 C11 C10 C9 -178.65(14) . .
C1 C2 C3 C4 19.45(14) . .
P1 C2 C3 C4 -162.57(11) . .
C15 C14 C15 C16 -1.6(3) 8_565 .
P1 C14 C15 C16 -179.54(11) . .
C14 C15 C16 C17 0.4(2) . .
C15 C16 C17 C16 0.9(3) . 8_565
C6 C7 C8 C9 -0.1(2) . .
C12 C7 C8 C9 179.01(14) . .
C7 C8 C9 C10 -0.7(2) . .
C11 C10 C9 C8 0.3(2) . .
C1 C5 C4 C3 27.65(14) . .
C2 C3 C4 C5 -28.62(14) . .
C21 C20 C19 C18 0.0 . .
C23 C18 C19 C20 0.0 . .
C23 C22 C21 C20 0.0 . .
C19 C20 C21 C22 0.0 . .
C19 C18 C23 C22 0.0 . .
C21 C22 C23 C18 0.0 . .
