 
data_AG15-4-5
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C26 H17 P' 
_chemical_formula_weight          360.36

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'
 'P'  'P'   0.2955   0.4335
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    12.2188(7)
_cell_length_b                    8.1128(5)
_cell_length_c                    18.0118(10)
_cell_angle_alpha                 90
_cell_angle_beta                  91.876(2)
_cell_angle_gamma                 90
_cell_volume                      1784.53(18)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used      9866
_cell_measurement_theta_min        4.31
_cell_measurement_theta_max       78.61
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.341          
_exptl_crystal_F_000              752
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.050
_exptl_crystal_size_min           0.020
_exptl_absorpt_coefficient_mu     1.396
_shelx_estimated_absorpt_T_min    0.768
_shelx_estimated_absorpt_T_max    0.973
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.8311
_exptl_absorpt_correction_T_max   0.9115
_exptl_absorpt_process_details    'SADABS Sheldrick 1996'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'rotating-anode X-ray tube'
_diffrn_measurement_device_type   'BrukerD8 goniometer'
_diffrn_measurement_method        'omega and phi scans'
_diffrn_detector_area_resol_mean  '10.24'
_diffrn_reflns_number             23358
_diffrn_reflns_av_unetI/netI      0.0178
_diffrn_reflns_av_R_equivalents   0.0302
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          4.308
_diffrn_reflns_theta_max          78.986
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.982
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.982
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.982
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3789
_reflns_number_gt                 3436
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'APEX2 (Bruker AXS, 2006)'
_computing_data_refinement        'SAINT (Bruker AXS, 2004)'
_computing_data_reduction         'SAINT (Bruker AXS, 2004)'
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material   'SHELXLE (Hübschle et al., 2011)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²+0.8466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3789
_refine_ls_number_parameters      244
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0384
_refine_ls_R_factor_gt            0.0347
_refine_ls_wR_factor_ref          0.0948
_refine_ls_wR_factor_gt           0.0919
_refine_ls_goodness_of_fit_ref    1.049
_refine_ls_restrained_S_all       1.049
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.40045(10) 0.54402(16) 0.39944(7) 0.0175(2) Uani 1 1 d . . . . .
C2 C 0.48913(10) 0.64215(16) 0.42837(7) 0.0169(2) Uani 1 1 d . . . . .
C3 C 0.47161(10) 0.75340(16) 0.48446(7) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.5311 0.8166 0.5044 0.022 Uiso 1 1 calc R U . . .
C4 C 0.36570(10) 0.77452(16) 0.51267(7) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.34507(11) 0.88750(16) 0.57079(7) 0.0207(3) Uani 1 1 d . . . . .
H5 H 0.4038 0.9497 0.5924 0.025 Uiso 1 1 calc R U . . .
C6 C 0.24157(12) 0.90766(17) 0.59598(7) 0.0239(3) Uani 1 1 d . . . . .
H6 H 0.2291 0.9838 0.6349 0.029 Uiso 1 1 calc R U . . .
C7 C 0.15338(11) 0.81659(18) 0.56486(8) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.0815 0.8339 0.5819 0.030 Uiso 1 1 calc R U . . .
C8 C 0.17063(11) 0.70318(18) 0.51008(7) 0.0233(3) Uani 1 1 d . . . . .
H8 H 0.1109 0.6402 0.4904 0.028 Uiso 1 1 calc R U . . .
C9 C 0.27679(10) 0.67885(16) 0.48243(7) 0.0191(3) Uani 1 1 d . . . . .
C10 C 0.29725(10) 0.56177(16) 0.42602(7) 0.0190(3) Uani 1 1 d . . . . .
H10 H 0.2391 0.4953 0.4066 0.023 Uiso 1 1 calc R U . . .
C11 C 0.58180(10) 0.48479(16) 0.33538(7) 0.0175(2) Uani 1 1 d . . . . .
C12 C 0.59310(10) 0.60672(15) 0.39237(7) 0.0166(3) Uani 1 1 d . . . . .
C13 C 0.69397(10) 0.67495(16) 0.40908(7) 0.0184(3) Uani 1 1 d . . . . .
H13 H 0.7013 0.7547 0.4475 0.022 Uiso 1 1 calc R U . . .
C14 C 0.78709(10) 0.62718(16) 0.36939(7) 0.0185(3) Uani 1 1 d . . . . .
C15 C 0.89255(11) 0.69458(17) 0.38562(7) 0.0219(3) Uani 1 1 d . . . . .
H15 H 0.9017 0.7733 0.4244 0.026 Uiso 1 1 calc R U . . .
C16 C 0.98130(11) 0.64729(18) 0.34603(8) 0.0246(3) Uani 1 1 d . . . . .
H16 H 1.0511 0.6943 0.3572 0.030 Uiso 1 1 calc R U . . .
C17 C 0.96935(11) 0.52898(18) 0.28884(8) 0.0252(3) Uani 1 1 d . . . . .
H17 H 1.0312 0.4972 0.2616 0.030 Uiso 1 1 calc R U . . .
C18 C 0.86914(11) 0.45967(18) 0.27235(7) 0.0229(3) Uani 1 1 d . . . . .
H18 H 0.8623 0.3790 0.2342 0.027 Uiso 1 1 calc R U . . .
C19 C 0.77524(10) 0.50736(16) 0.31176(7) 0.0190(3) Uani 1 1 d . . . . .
C20 C 0.67103(10) 0.43551(16) 0.29658(7) 0.0192(3) Uani 1 1 d . . . . .
H20 H 0.6629 0.3529 0.2594 0.023 Uiso 1 1 calc R U . . .
C21 C 0.38121(10) 0.47401(16) 0.24492(7) 0.0173(2) Uani 1 1 d . . . . .
C22 C 0.42495(11) 0.59921(16) 0.20206(7) 0.0209(3) Uani 1 1 d . . . . .
H22 H 0.4927 0.6487 0.2168 0.025 Uiso 1 1 calc R U . . .
C23 C 0.36935(11) 0.65185(19) 0.13766(8) 0.0257(3) Uani 1 1 d . . . . .
H23 H 0.3996 0.7369 0.1084 0.031 Uiso 1 1 calc R U . . .
C24 C 0.27025(12) 0.5813(2) 0.11588(7) 0.0265(3) Uani 1 1 d . . . . .
H24 H 0.2327 0.6182 0.0720 0.032 Uiso 1 1 calc R U . . .
C25 C 0.22599(11) 0.45691(19) 0.15809(7) 0.0249(3) Uani 1 1 d . . . . .
H25 H 0.1576 0.4092 0.1435 0.030 Uiso 1 1 calc R U . . .
C26 C 0.28174(11) 0.40196(17) 0.22190(7) 0.0212(3) Uani 1 1 d . . . . .
H26 H 0.2520 0.3148 0.2501 0.025 Uiso 1 1 calc R U . . .
P1 P 0.44552(3) 0.39329(4) 0.33111(2) 0.01729(10) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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
C1 C10 1.3709(18) . ?
C1 C2 1.4292(17) . ?
C1 P1 1.8325(13) . ?
C2 C3 1.3766(18) . ?
C2 C12 1.4735(17) . ?
C3 C4 1.4161(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4201(18) . ?
C4 C9 1.4285(18) . ?
C5 C6 1.3673(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.4184(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4191(18) . ?
C10 H10 0.9500 . ?
C11 C20 1.3736(17) . ?
C11 C12 1.4290(17) . ?
C11 P1 1.8224(13) . ?
C12 C13 1.3754(18) . ?
C13 C14 1.4176(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.4214(18) . ?
C14 C19 1.4260(18) . ?
C15 C16 1.3719(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.412(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.371(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.4224(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.4189(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3929(18) . ?
C21 C26 1.3992(18) . ?
C21 P1 1.8375(13) . ?
C22 C23 1.3920(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3901(19) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
 
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
C10 C1 C2 120.61(12) . . ?
C10 C1 P1 127.21(10) . . ?
C2 C1 P1 112.07(9) . . ?
C3 C2 C1 119.90(11) . . ?
C3 C2 C12 127.44(11) . . ?
C1 C2 C12 112.65(11) . . ?
C2 C3 C4 120.57(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.94(12) . . ?
C3 C4 C9 119.34(11) . . ?
C5 C4 C9 118.73(12) . . ?
C6 C5 C4 120.69(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.61(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.35(13) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.68(13) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 121.94(12) . . ?
C8 C9 C4 118.90(12) . . ?
C10 C9 C4 119.15(11) . . ?
C1 C10 C9 120.39(12) . . ?
C1 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C20 C11 C12 120.48(12) . . ?
C20 C11 P1 126.82(10) . . ?
C12 C11 P1 112.27(9) . . ?
C13 C12 C11 120.05(12) . . ?
C13 C12 C2 127.19(12) . . ?
C11 C12 C2 112.75(11) . . ?
C12 C13 C14 120.52(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 121.90(12) . . ?
C13 C14 C19 119.31(12) . . ?
C15 C14 C19 118.80(12) . . ?
C16 C15 C14 120.81(13) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.31(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.47(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.64(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 121.70(12) . . ?
C20 C19 C14 119.30(11) . . ?
C18 C19 C14 118.97(12) . . ?
C11 C20 C19 120.31(12) . . ?
C11 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C26 119.07(12) . . ?
C22 C21 P1 124.52(10) . . ?
C26 C21 P1 116.41(10) . . ?
C23 C22 C21 119.98(12) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.51(13) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.98(13) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.89(13) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 120.55(12) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C11 P1 C1 89.66(6) . . ?
C11 P1 C21 104.80(6) . . ?
C1 P1 C21 101.53(6) . . ?
 
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
C10 C1 C2 C3 1.27(18) . . . . ?
P1 C1 C2 C3 -175.14(9) . . . . ?
C10 C1 C2 C12 -179.37(11) . . . . ?
P1 C1 C2 C12 4.22(13) . . . . ?
C1 C2 C3 C4 -1.51(18) . . . . ?
C12 C2 C3 C4 179.23(12) . . . . ?
C2 C3 C4 C5 179.61(12) . . . . ?
C2 C3 C4 C9 0.10(18) . . . . ?
C3 C4 C5 C6 178.74(12) . . . . ?
C9 C4 C5 C6 -1.74(18) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C6 C7 C8 C9 -1.7(2) . . . . ?
C7 C8 C9 C10 179.68(12) . . . . ?
C7 C8 C9 C4 0.05(19) . . . . ?
C3 C4 C9 C8 -178.80(11) . . . . ?
C5 C4 C9 C8 1.67(18) . . . . ?
C3 C4 C9 C10 1.56(18) . . . . ?
C5 C4 C9 C10 -177.97(11) . . . . ?
C2 C1 C10 C9 0.42(19) . . . . ?
P1 C1 C10 C9 176.24(9) . . . . ?
C8 C9 C10 C1 178.56(12) . . . . ?
C4 C9 C10 C1 -1.81(18) . . . . ?
C20 C11 C12 C13 -0.42(18) . . . . ?
P1 C11 C12 C13 172.59(9) . . . . ?
C20 C11 C12 C2 -179.28(11) . . . . ?
P1 C11 C12 C2 -6.27(13) . . . . ?
C3 C2 C12 C13 1.8(2) . . . . ?
C1 C2 C12 C13 -177.46(12) . . . . ?
C3 C2 C12 C11 -179.39(12) . . . . ?
C1 C2 C12 C11 1.30(15) . . . . ?
C11 C12 C13 C14 0.98(18) . . . . ?
C2 C12 C13 C14 179.65(11) . . . . ?
C12 C13 C14 C15 -179.60(12) . . . . ?
C12 C13 C14 C19 0.00(18) . . . . ?
C13 C14 C15 C16 -179.51(12) . . . . ?
C19 C14 C15 C16 0.89(19) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C20 -178.94(12) . . . . ?
C17 C18 C19 C14 -0.72(19) . . . . ?
C13 C14 C19 C20 -1.53(18) . . . . ?
C15 C14 C19 C20 178.09(12) . . . . ?
C13 C14 C19 C18 -179.79(11) . . . . ?
C15 C14 C19 C18 -0.17(18) . . . . ?
C12 C11 C20 C19 -1.13(19) . . . . ?
P1 C11 C20 C19 -173.04(10) . . . . ?
C18 C19 C20 C11 -179.70(12) . . . . ?
C14 C19 C20 C11 2.09(18) . . . . ?
C26 C21 C22 C23 0.51(19) . . . . ?
P1 C21 C22 C23 -179.79(10) . . . . ?
C21 C22 C23 C24 0.3(2) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 C26 -0.7(2) . . . . ?
C24 C25 C26 C21 1.5(2) . . . . ?
C22 C21 C26 C25 -1.44(19) . . . . ?
P1 C21 C26 C25 178.83(10) . . . . ?
C20 C11 P1 C1 179.67(12) . . . . ?
C12 C11 P1 C1 7.20(9) . . . . ?
C20 C11 P1 C21 -78.48(12) . . . . ?
C12 C11 P1 C21 109.05(9) . . . . ?
C10 C1 P1 C11 177.42(12) . . . . ?
C2 C1 P1 C11 -6.45(9) . . . . ?
C10 C1 P1 C21 72.39(12) . . . . ?
C2 C1 P1 C21 -111.49(9) . . . . ?
C22 C21 P1 C11 -9.75(12) . . . . ?
C26 C21 P1 C11 169.96(10) . . . . ?
C22 C21 P1 C1 82.99(12) . . . . ?
C26 C21 P1 C1 -97.31(10) . . . . ?
 
_refine_diff_density_max    0.439
_refine_diff_density_min   -0.250
_refine_diff_density_rms    0.051



