#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/06/67/4066713.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_4066713
loop_
_publ_author_name
'Objartel, Ina'
'Pott, Nils A.'
'John, Michael'
'Stalke, Dietmar'
_publ_contact_author             'Prof. Dr. D. Stalke'
_publ_section_title
;
 Coordination Site SelectiveJanus HeadLigands†
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              5670
_journal_paper_doi               10.1021/om1005885
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C18 H17 N2 P'
_chemical_formula_weight         292.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1084(12)
_cell_length_b                   5.5316(4)
_cell_length_c                   17.9425(14)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7685
_cell_measurement_theta_min      2.3175
_cell_volume                     1487.67(19)
_computing_cell_refinement       'SAINT V7.46A'
_computing_data_collection       'APEX2 v2.2-0'
_computing_data_reduction        'SAINT V7.46A'
_computing_molecular_graphics    'XSHELL vers. 4.01'
_computing_publication_material  'XSHELL vers. 4.01'
_computing_structure_refinement  'SHELXL in SHELXTL Ver. 6.10'
_computing_structure_solution    'SHELXS in SHELXTL Ver. 6.10'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker TXS-Mo rotating anode'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'INCOATEC Helios Mirror optics'
_diffrn_radiation_source         'Bruker TXS-Mo rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            36407
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS-2008/2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.8571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0743
_reflns_number_gt                2746
_reflns_number_total             3032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1005885_si_002.cif
_cod_data_source_block           p21c
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4066713
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_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
P1 P 0.16387(2) 0.41727(6) 0.115281(19) 0.01789(9) Uani 1 1 d .
N1 N 0.31657(7) 0.5327(2) 0.29409(7) 0.0232(2) Uani 1 1 d .
N2 N -0.05342(7) 0.3875(2) 0.09008(6) 0.0208(2) Uani 1 1 d .
C1 C 0.22082(8) 0.2290(2) 0.20622(7) 0.0206(3) Uani 1 1 d .
H1A H 0.1839 0.2262 0.2398 0.025 Uiso 1 1 calc R
H1B H 0.2261 0.0609 0.1895 0.025 Uiso 1 1 calc R
C2 C 0.31206(8) 0.3231(2) 0.25504(7) 0.0192(3) Uani 1 1 d .
C3 C 0.38815(9) 0.1967(3) 0.25869(8) 0.0228(3) Uani 1 1 d .
H3 H 0.3831 0.0511 0.2292 0.027 Uiso 1 1 calc R
C4 C 0.47139(9) 0.2850(3) 0.30563(8) 0.0269(3) Uani 1 1 d .
H4 H 0.5240 0.2004 0.3091 0.032 Uiso 1 1 calc R
C5 C 0.47668(9) 0.4981(3) 0.34729(8) 0.0273(3) Uani 1 1 d .
H5 H 0.5327 0.5626 0.3805 0.033 Uiso 1 1 calc R
C6 C 0.39789(9) 0.6147(3) 0.33912(8) 0.0258(3) Uani 1 1 d .
H6 H 0.4016 0.7623 0.3672 0.031 Uiso 1 1 calc R
C7 C 0.07050(8) 0.2094(2) 0.06283(7) 0.0191(3) Uani 1 1 d .
H7A H 0.0407 0.2636 0.0067 0.023 Uiso 1 1 calc R
H7B H 0.0945 0.0451 0.0619 0.023 Uiso 1 1 calc R
C8 C 0.00308(8) 0.1999(2) 0.10276(7) 0.0176(3) Uani 1 1 d .
C9 C 0.00051(8) 0.0037(2) 0.15037(7) 0.0196(3) Uani 1 1 d .
H9 H 0.0411 -0.1269 0.1579 0.023 Uiso 1 1 calc R
C10 C -0.06223(9) 0.0012(2) 0.18670(8) 0.0217(3) Uani 1 1 d .
H10 H -0.0648 -0.1302 0.2199 0.026 Uiso 1 1 calc R
C11 C -0.12093(8) 0.1928(3) 0.17377(7) 0.0210(3) Uani 1 1 d .
H11 H -0.1648 0.1962 0.1976 0.025 Uiso 1 1 calc R
C12 C -0.11395(8) 0.3793(3) 0.12515(8) 0.0217(3) Uani 1 1 d .
H12 H -0.1547 0.5102 0.1160 0.026 Uiso 1 1 calc R
C13 C 0.23911(8) 0.3630(2) 0.06067(7) 0.0180(3) Uani 1 1 d .
C14 C 0.23599(9) 0.1607(2) 0.01316(8) 0.0211(3) Uani 1 1 d .
H14 H 0.1945 0.0351 0.0096 0.025 Uiso 1 1 calc R
C15 C 0.29288(9) 0.1407(3) -0.02908(8) 0.0224(3) Uani 1 1 d .
H15 H 0.2896 0.0026 -0.0615 0.027 Uiso 1 1 calc R
C16 C 0.35445(9) 0.3213(3) -0.02413(8) 0.0229(3) Uani 1 1 d .
H16 H 0.3931 0.3076 -0.0531 0.027 Uiso 1 1 calc R
C17 C 0.35903(9) 0.5215(3) 0.02333(8) 0.0251(3) Uani 1 1 d .
H17 H 0.4014 0.6451 0.0275 0.030 Uiso 1 1 calc R
C18 C 0.30158(9) 0.5423(2) 0.06504(8) 0.0221(3) Uani 1 1 d .
H18 H 0.3050 0.6813 0.0971 0.026 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 P1 C7 101.46(6)
C13 P1 C1 99.53(6)
C7 P1 C1 98.35(6)
C6 N1 C2 117.43(12)
C12 N2 C8 117.28(11)
C2 C1 P1 112.26(9)
C2 C1 H1A 109.2
P1 C1 H1A 109.2
C2 C1 H1B 109.2
P1 C1 H1B 109.2
H1A C1 H1B 107.9
N1 C2 C3 122.06(12)
N1 C2 C1 117.26(11)
C3 C2 C1 120.69(12)
C4 C3 C2 119.43(13)
C4 C3 H3 120.3
C2 C3 H3 120.3
C5 C4 C3 118.94(13)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C5 C6 117.91(13)
C4 C5 H5 121.0
C6 C5 H5 121.0
N1 C6 C5 124.21(13)
N1 C6 H6 117.9
C5 C6 H6 117.9
C8 C7 P1 111.90(8)
C8 C7 H7A 109.2
P1 C7 H7A 109.2
C8 C7 H7B 109.2
P1 C7 H7B 109.2
H7A C7 H7B 107.9
N2 C8 C9 122.40(11)
N2 C8 C7 117.03(11)
C9 C8 C7 120.57(11)
C10 C9 C8 119.11(12)
C10 C9 H9 120.4
C8 C9 H9 120.4
C11 C10 C9 118.96(12)
C11 C10 H10 120.5
C9 C10 H10 120.5
C12 C11 C10 118.01(12)
C12 C11 H11 121.0
C10 C11 H11 121.0
N2 C12 C11 124.24(12)
N2 C12 H12 117.9
C11 C12 H12 117.9
C18 C13 C14 117.92(12)
C18 C13 P1 117.16(10)
C14 C13 P1 124.88(10)
C15 C14 C13 120.84(12)
C15 C14 H14 119.6
C13 C14 H14 119.6
C16 C15 C14 120.39(13)
C16 C15 H15 119.8
C14 C15 H15 119.8
C17 C16 C15 119.46(12)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C18 120.11(13)
C16 C17 H17 119.9
C18 C17 H17 119.9
C17 C18 C13 121.29(13)
C17 C18 H18 119.4
C13 C18 H18 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C13 1.8410(13)
P1 C7 1.8528(13)
P1 C1 1.8686(13)
N1 C6 1.3413(18)
N1 C2 1.3428(18)
N2 C12 1.3409(17)
N2 C8 1.3438(17)
C1 C2 1.5017(17)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.3917(18)
C3 C4 1.3851(19)
C3 H3 0.9500
C4 C5 1.382(2)
C4 H4 0.9500
C5 C6 1.383(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5052(16)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.3912(18)
C9 C10 1.3889(18)
C9 H9 0.9500
C10 C11 1.3823(19)
C10 H10 0.9500
C11 C12 1.3820(19)
C11 H11 0.9500
C12 H12 0.9500
C13 C18 1.3942(18)
C13 C14 1.3965(18)
C14 C15 1.3912(18)
C14 H14 0.9500
C15 C16 1.3877(19)
C15 H15 0.9500
C16 C17 1.382(2)
C16 H16 0.9500
C17 C18 1.3918(18)
C17 H17 0.9500
C18 H18 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
C13 P1 C1 C2 64.69(10)
C7 P1 C1 C2 167.88(9)
C6 N1 C2 C3 -1.72(18)
C6 N1 C2 C1 178.63(11)
P1 C1 C2 N1 69.83(13)
P1 C1 C2 C3 -109.82(12)
N1 C2 C3 C4 1.8(2)
C1 C2 C3 C4 -178.57(12)
C2 C3 C4 C5 -0.5(2)
C3 C4 C5 C6 -0.7(2)
C2 N1 C6 C5 0.4(2)
C4 C5 C6 N1 0.8(2)
C13 P1 C7 C8 173.79(9)
C1 P1 C7 C8 72.22(10)
C12 N2 C8 C9 -0.30(18)
C12 N2 C8 C7 179.64(11)
P1 C7 C8 N2 76.76(12)
P1 C7 C8 C9 -103.30(12)
N2 C8 C9 C10 -0.40(19)
C7 C8 C9 C10 179.66(11)
C8 C9 C10 C11 0.66(18)
C9 C10 C11 C12 -0.23(18)
C8 N2 C12 C11 0.78(19)
C10 C11 C12 N2 -0.5(2)
C7 P1 C13 C18 158.99(10)
C1 P1 C13 C18 -100.39(11)
C7 P1 C13 C14 -18.57(12)
C1 P1 C13 C14 82.05(12)
C18 C13 C14 C15 -0.71(19)
P1 C13 C14 C15 176.84(10)
C13 C14 C15 C16 0.6(2)
C14 C15 C16 C17 0.2(2)
C15 C16 C17 C18 -0.7(2)
C16 C17 C18 C13 0.5(2)
C14 C13 C18 C17 0.17(19)
P1 C13 C18 C17 -177.57(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10452595
