#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:09:15 +0100 (vie 25 de mar de 2016) $
#$Revision: 179954 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/49/7024980.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_7024980
loop_
_publ_author_name
'Seacome, Richard J.'
'Coles, Martyn P.'
'Glover, Jean E.'
'Hitchcock, Peter B.'
'Rowlands, Gareth J.'
_publ_section_title
;
 Planar-chiral imidazole-based phosphine ligands derived from
 [2.2]paracyclophane
;
_journal_issue                   15
_journal_name_full               'Dalton Transactions'
_journal_page_first              3687
_journal_paper_doi               10.1039/b923716j
_journal_volume                  39
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H35 N2 O P, 0.5(C6 H12)'
_chemical_formula_sum            'C30 H41 N2 O P'
_chemical_formula_weight         476.62
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2008-01-14T10:55:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.127(1)
_cell_angle_beta                 105.574(2)
_cell_angle_gamma                102.542(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1186(3)
_cell_length_b                   11.6152(3)
_cell_length_c                   13.9871(4)
_cell_measurement_reflns_used    10388
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.022
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     1310.24(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.11235
_diffrn_orient_matrix_UB_12      0.20079E-2
_diffrn_orient_matrix_UB_13      -0.27018E-1
_diffrn_orient_matrix_UB_21      -0.04095
_diffrn_orient_matrix_UB_22      -0.922963E-1
_diffrn_orient_matrix_UB_23      -0.148763E-1
_diffrn_orient_matrix_UB_31      -0.53105E-2
_diffrn_orient_matrix_UB_32      0.164309E-1
_diffrn_orient_matrix_UB_33      0.72629E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18924
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0729P)²+1.2169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                4188
_reflns_number_total             5112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923716j.txt
_cod_data_source_block           (3)-jan808
_cod_database_code               7024980
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
P P 0.36043(6) 0.17290(5) 0.27134(4) 0.02125(17) Uani 1 1 d .
O O 0.40850(18) 0.27203(14) 0.37549(12) 0.0269(4) Uani 1 1 d .
N1 N 0.5248(2) 0.33610(17) 0.18402(14) 0.0241(4) Uani 1 1 d .
N2 N 0.3245(2) 0.16852(19) 0.06813(15) 0.0324(5) Uani 1 1 d .
C1 C 0.4584(3) 0.6600(2) 0.3252(2) 0.0360(6) Uani 1 1 d .
H1A H 0.3674 0.6511 0.2632 0.043 Uiso 1 1 calc R
H1B H 0.4492 0.7165 0.3884 0.043 Uiso 1 1 calc R
C2 C 0.4459(3) 0.5269(2) 0.3375(2) 0.0291(5) Uani 1 1 d .
H2A H 0.4071 0.5228 0.3965 0.035 Uiso 1 1 calc R
H2B H 0.3664 0.4613 0.2722 0.035 Uiso 1 1 calc R
C3 C 0.6041(2) 0.50006(19) 0.35798(17) 0.0221(4) Uani 1 1 d .
C4 C 0.6449(2) 0.42536(19) 0.28003(17) 0.0218(4) Uani 1 1 d .
C5 C 0.8044(3) 0.4460(2) 0.28600(19) 0.0258(5) Uani 1 1 d .
H5 H 0.8296 0.3961 0.2309 0.031 Uiso 1 1 calc R
C6 C 0.9263(3) 0.5390(2) 0.37190(19) 0.0265(5) Uani 1 1 d .
C7 C 0.8873(3) 0.5904(2) 0.45987(18) 0.0264(5) Uani 1 1 d .
H7 H 0.9702 0.6389 0.5254 0.032 Uiso 1 1 calc R
C8 C 0.7289(3) 0.5712(2) 0.45259(18) 0.0250(5) Uani 1 1 d .
H8 H 0.7048 0.6074 0.5134 0.03 Uiso 1 1 calc R
C9 C 1.0835(3) 0.5993(2) 0.3628(2) 0.0347(6) Uani 1 1 d .
H9A H 1.1031 0.5392 0.3066 0.042 Uiso 1 1 calc R
H9B H 1.1708 0.6184 0.43 0.042 Uiso 1 1 calc R
C10 C 1.0879(3) 0.7248(3) 0.3365(2) 0.0408(6) Uani 1 1 d .
H10A H 1.1715 0.7959 0.3957 0.049 Uiso 1 1 calc R
H10B H 1.1178 0.7183 0.2727 0.049 Uiso 1 1 calc R
C11 C 0.9297(3) 0.7520(2) 0.3179(2) 0.0312(5) Uani 1 1 d .
C12 C 0.8027(3) 0.6846(2) 0.2245(2) 0.0335(6) Uani 1 1 d .
H12 H 0.8233 0.6487 0.1621 0.04 Uiso 1 1 calc R
C13 C 0.6455(3) 0.6689(2) 0.22101(19) 0.0307(5) Uani 1 1 d .
H13 H 0.5597 0.6233 0.1562 0.037 Uiso 1 1 calc R
C14 C 0.6131(3) 0.7196(2) 0.31181(19) 0.0282(5) Uani 1 1 d .
C15 C 0.7394(3) 0.8087(2) 0.39716(19) 0.0295(5) Uani 1 1 d .
H15 H 0.7182 0.8591 0.4541 0.035 Uiso 1 1 calc R
C16 C 0.8968(3) 0.8254(2) 0.4007(2) 0.0311(5) Uani 1 1 d .
H16 H 0.982 0.887 0.4597 0.037 Uiso 1 1 calc R
C17 C 0.4034(3) 0.2316(2) 0.16967(17) 0.0241(5) Uani 1 1 d .
C18 C 0.3965(3) 0.2337(2) 0.01526(19) 0.0356(6) Uani 1 1 d .
H18 H 0.3645 0.2106 -0.0593 0.043 Uiso 1 1 calc R
C19 C 0.5195(3) 0.3357(2) 0.08445(18) 0.0318(5) Uani 1 1 d .
H19 H 0.5884 0.3951 0.0676 0.038 Uiso 1 1 calc R
C20 C 0.4801(3) 0.0633(2) 0.28142(19) 0.0303(5) Uani 1 1 d .
C21 C 0.4400(4) -0.0034(3) 0.3563(3) 0.0542(8) Uani 1 1 d .
H21A H 0.3311 -0.0621 0.3225 0.081 Uiso 1 1 calc R
H21B H 0.4473 0.0587 0.4215 0.081 Uiso 1 1 calc R
H21C H 0.516 -0.0495 0.3728 0.081 Uiso 1 1 calc R
C22 C 0.4621(5) -0.0315(3) 0.1773(3) 0.0637(10) Uani 1 1 d .
H22A H 0.5383 -0.0784 0.19 0.096 Uiso 1 1 calc R
H22B H 0.4835 0.0126 0.1292 0.096 Uiso 1 1 calc R
H22C H 0.3528 -0.0897 0.1457 0.096 Uiso 1 1 calc R
C23 C 0.6548(3) 0.1469(3) 0.3329(3) 0.0549(8) Uani 1 1 d .
H23A H 0.724 0.0959 0.35 0.082 Uiso 1 1 calc R
H23B H 0.667 0.2123 0.3976 0.082 Uiso 1 1 calc R
H23C H 0.6851 0.1859 0.2839 0.082 Uiso 1 1 calc R
C24 C 0.1400(3) 0.0970(2) 0.21886(19) 0.0295(5) Uani 1 1 d .
C25 C 0.0892(3) 0.0783(3) 0.3114(2) 0.0385(6) Uani 1 1 d .
H25A H -0.0277 0.044 0.2875 0.058 Uiso 1 1 calc R
H25B H 0.1249 0.1592 0.3684 0.058 Uiso 1 1 calc R
H25C H 0.1378 0.0199 0.3372 0.058 Uiso 1 1 calc R
C26 C 0.0794(3) -0.0287(3) 0.1284(2) 0.0441(7) Uani 1 1 d .
H26A H 0.1139 -0.092 0.1551 0.066 Uiso 1 1 calc R
H26B H 0.1233 -0.0193 0.0731 0.066 Uiso 1 1 calc R
H26C H -0.0378 -0.0551 0.0991 0.066 Uiso 1 1 calc R
C27 C 0.0632(3) 0.1911(3) 0.1823(2) 0.0425(7) Uani 1 1 d .
H27A H 0.0865 0.1999 0.1197 0.064 Uiso 1 1 calc R
H27B H 0.1072 0.2727 0.239 0.064 Uiso 1 1 calc R
H27C H -0.0529 0.1604 0.165 0.064 Uiso 1 1 calc R
C28 C -0.0821(5) 0.3813(3) -0.0096(3) 0.0610(9) Uani 1 1 d .
H28A H -0.1133 0.3343 -0.0857 0.073 Uiso 1 1 calc R
H28B H -0.1214 0.3221 0.0243 0.073 Uiso 1 1 calc R
C29 C 0.0943(4) 0.4325(3) 0.0373(3) 0.0587(9) Uani 1 1 d .
H29A H 0.1259 0.4711 0.1148 0.07 Uiso 1 1 calc R
H29B H 0.1412 0.3633 0.0231 0.07 Uiso 1 1 calc R
C30 C 0.1549(3) 0.5218(2) -0.0035(2) 0.0362(6) Uani 1 1 d .
H30A H 0.1346 0.4812 -0.0794 0.043 Uiso 1 1 calc R
H30B H 0.2721 0.5583 0.0331 0.043 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 0 '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'
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'
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
O P C17 113.85(9) . .
O P C20 109.85(10) . .
C17 P C20 103.49(10) . .
O P C24 110.16(10) . .
C17 P C24 104.67(10) . .
C20 P C24 114.69(11) . .
C19 N1 C17 106.23(18) . .
C19 N1 C4 124.07(18) . .
C17 N1 C4 129.53(18) . .
C17 N2 C18 105.7(2) . .
C14 C1 C2 113.35(18) . .
C14 C1 H1A 108.9 . .
C2 C1 H1A 108.9 . .
C14 C1 H1B 108.9 . .
C2 C1 H1B 108.9 . .
H1A C1 H1B 107.7 . .
C3 C2 C1 112.50(18) . .
C3 C2 H2A 109.1 . .
C1 C2 H2A 109.1 . .
C3 C2 H2B 109.1 . .
C1 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
C8 C3 C4 116.05(19) . .
C8 C3 C2 119.24(19) . .
C4 C3 C2 123.5(2) . .
C3 C4 C5 120.9(2) . .
C3 C4 N1 121.52(19) . .
C5 C4 N1 117.03(19) . .
C6 C5 C4 120.5(2) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C7 117.1(2) . .
C5 C6 C9 121.2(2) . .
C7 C6 C9 120.7(2) . .
C8 C7 C6 120.6(2) . .
C8 C7 H7 119.7 . .
C6 C7 H7 119.7 . .
C7 C8 C3 121.4(2) . .
C7 C8 H8 119.3 . .
C3 C8 H8 119.3 . .
C6 C9 C10 112.72(19) . .
C6 C9 H9A 109 . .
C10 C9 H9A 109 . .
C6 C9 H9B 109 . .
C10 C9 H9B 109 . .
H9A C9 H9B 107.8 . .
C11 C10 C9 113.05(19) . .
C11 C10 H10A 109 . .
C9 C10 H10A 109 . .
C11 C10 H10B 109 . .
C9 C10 H10B 109 . .
H10A C10 H10B 107.8 . .
C12 C11 C16 117.4(2) . .
C12 C11 C10 120.5(2) . .
C16 C11 C10 120.8(2) . .
C11 C12 C13 120.8(2) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C14 C13 C12 120.4(2) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C15 C14 C13 117.2(2) . .
C15 C14 C1 120.6(2) . .
C13 C14 C1 120.9(2) . .
C14 C15 C16 121.0(2) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C15 C16 C11 120.1(2) . .
C15 C16 H16 119.9 . .
C11 C16 H16 119.9 . .
N2 C17 N1 111.05(19) . .
N2 C17 P 121.50(16) . .
N1 C17 P 127.23(16) . .
C19 C18 N2 110.5(2) . .
C19 C18 H18 124.7 . .
N2 C18 H18 124.7 . .
C18 C19 N1 106.5(2) . .
C18 C19 H19 126.8 . .
N1 C19 H19 126.8 . .
C22 C20 C21 110.6(2) . .
C22 C20 C23 108.3(2) . .
C21 C20 C23 108.2(2) . .
C22 C20 P 115.62(19) . .
C21 C20 P 108.50(17) . .
C23 C20 P 105.20(17) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C26 C24 C25 109.4(2) . .
C26 C24 C27 109.8(2) . .
C25 C24 C27 107.6(2) . .
C26 C24 P 115.39(18) . .
C25 C24 P 107.36(16) . .
C27 C24 P 107.05(16) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C30 C28 C29 111.4(3) 2_565 .
C30 C28 H28A 109.3 2_565 .
C29 C28 H28A 109.3 . .
C30 C28 H28B 109.3 2_565 .
C29 C28 H28B 109.3 . .
H28A C28 H28B 108 . .
C30 C29 C28 111.6(3) . .
C30 C29 H29A 109.3 . .
C28 C29 H29A 109.3 . .
C30 C29 H29B 109.3 . .
C28 C29 H29B 109.3 . .
H29A C29 H29B 108 . .
C29 C30 C28 110.8(2) . 2_565
C29 C30 H30A 109.5 . .
C28 C30 H30A 109.5 2_565 .
C29 C30 H30B 109.5 . .
C28 C30 H30B 109.5 2_565 .
H30A C30 H30B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P O 1.4841(15) .
P C17 1.825(2) .
P C20 1.857(2) .
P C24 1.859(2) .
N1 C19 1.379(3) .
N1 C17 1.381(3) .
N1 C4 1.438(3) .
N2 C17 1.323(3) .
N2 C18 1.374(3) .
C1 C14 1.513(3) .
C1 C2 1.583(3) .
C1 H1A 0.99 .
C1 H1B 0.99 .
C2 C3 1.510(3) .
C2 H2A 0.99 .
C2 H2B 0.99 .
C3 C8 1.393(3) .
C3 C4 1.394(3) .
C4 C5 1.398(3) .
C5 C6 1.390(3) .
C5 H5 0.95 .
C6 C7 1.393(3) .
C6 C9 1.506(3) .
C7 C8 1.384(3) .
C7 H7 0.95 .
C8 H8 0.95 .
C9 C10 1.589(3) .
C9 H9A 0.99 .
C9 H9B 0.99 .
C10 C11 1.512(3) .
C10 H10A 0.99 .
C10 H10B 0.99 .
C11 C12 1.386(4) .
C11 C16 1.393(3) .
C12 C13 1.392(3) .
C12 H12 0.95 .
C13 C14 1.390(3) .
C13 H13 0.95 .
C14 C15 1.386(3) .
C15 C16 1.391(3) .
C15 H15 0.95 .
C16 H16 0.95 .
C18 C19 1.356(4) .
C18 H18 0.95 .
C19 H19 0.95 .
C20 C22 1.521(4) .
C20 C21 1.528(4) .
C20 C23 1.532(4) .
C21 H21A 0.98 .
C21 H21B 0.98 .
C21 H21C 0.98 .
C22 H22A 0.98 .
C22 H22B 0.98 .
C22 H22C 0.98 .
C23 H23A 0.98 .
C23 H23B 0.98 .
C23 H23C 0.98 .
C24 C26 1.532(3) .
C24 C25 1.537(3) .
C24 C27 1.542(3) .
C25 H25A 0.98 .
C25 H25B 0.98 .
C25 H25C 0.98 .
C26 H26A 0.98 .
C26 H26B 0.98 .
C26 H26C 0.98 .
C27 H27A 0.98 .
C27 H27B 0.98 .
C27 H27C 0.98 .
C28 C30 1.422(4) 2_565
C28 C29 1.479(5) .
C28 H28A 0.99 .
C28 H28B 0.99 .
C29 C30 1.392(4) .
C29 H29A 0.99 .
C29 H29B 0.99 .
C30 C28 1.422(4) 2_565
C30 H30A 0.99 .
C30 H30B 0.99 .
