# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mbkp_205_0m
_database_code_depnum_ccdc_archive 'CCDC 1410349'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2013 template'

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 P'
_chemical_formula_sum            'C23 H21 P'
_chemical_formula_weight         328.37

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# Crystal Data

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3278(4)
_cell_length_b                   17.6372(8)
_cell_length_c                   12.0862(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.553(3)
_cell_angle_gamma                90
_cell_volume                     1771.80(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5343
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.21

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.158
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_T_max  0.7421
_exptl_absorpt_process_details   'SADABS v2012/1 (Apex2, Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15480
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         27.208
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3945
_reflns_number_gt                2994
_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 software package v2013.10-0 (Bruker AXS)
;
_computing_cell_refinement       
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)
;
_computing_data_reduction        
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS
;
_computing_structure_solution    
; 'SHELXT-2014 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
; XP (SHELXTL-NT v6.14, Bruker AXS)
;

# REFINEMENT DATA

_refine_special_details          
;The non-hydrogen atoms were refined anisotropically. Hydrogen atoms of the
 phenyl- and CH-, CH₂- and CH₃-groups were included at geometrically 
 idealized   positions (C-H bond distances 0.95/0.99/0.98 ) and were not
 refined. The isotropic thermal parameters of these hydrogen atoms were fixed
 at 1.2 (phenyl-, CH- and CH₂-groups) and 1.5 times (CH₃-groups) that of
 the preceding carbon.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0449P)²+0.5900P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.39832(5) 0.23945(3) 0.60343(4) 0.02802(13) Uani 1 1 d . . . . .
C1 C 0.44646(18) 0.16736(9) 0.50173(13) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.59631(19) 0.15101(10) 0.47293(15) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.6893 0.1786 0.4986 0.038 Uiso 1 1 calc R U . . .
C3 C 0.60020(19) 0.08502(10) 0.39648(15) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.6659 0.0432 0.4299 0.038 Uiso 1 1 calc R U . . .
H3B H 0.6433 0.0996 0.3250 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3592(2) 0.00490(9) 0.31751(14) 0.0321(4) Uani 1 1 d . . . . .
C5 C 0.1940(2) -0.00541(10) 0.32047(15) 0.0376(4) Uani 1 1 d . . . . .
H5 H 0.1430 -0.0448 0.2778 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1024(2) 0.04082(10) 0.38462(14) 0.0345(4) Uani 1 1 d . . . . .
H6 H -0.0099 0.0315 0.3852 0.041 Uiso 1 1 calc R U . . .
C7 C 0.16814(19) 0.10033(9) 0.44826(14) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.33469(18) 0.11146(9) 0.44612(13) 0.0248(3) Uani 1 1 d . . . . .
C9 C 0.42638(19) 0.06319(9) 0.38168(14) 0.0273(4) Uani 1 1 d . . . . .
C10 C 0.4615(3) -0.04298(11) 0.24695(16) 0.0451(5) Uani 1 1 d . . . . .
H10A H 0.5199 -0.0102 0.1977 0.068 Uiso 1 1 calc R U . . .
H10B H 0.3928 -0.0780 0.2025 0.068 Uiso 1 1 calc R U . . .
H10C H 0.5386 -0.0720 0.2947 0.068 Uiso 1 1 calc R U . . .
C11 C 0.06060(19) 0.14832(11) 0.51563(15) 0.0353(4) Uani 1 1 d . . . . .
H11A H 0.0480 0.1986 0.4817 0.053 Uiso 1 1 calc R U . . .
H11B H 0.1089 0.1535 0.5913 0.053 Uiso 1 1 calc R U . . .
H11C H -0.0450 0.1241 0.5177 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6020(2) 0.27461(10) 0.64084(14) 0.0311(4) Uani 1 1 d . . . . .
C13 C 0.6788(2) 0.24473(10) 0.73661(16) 0.0378(4) Uani 1 1 d . . . . .
H13 H 0.6209 0.2128 0.7833 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8389(2) 0.26113(12) 0.76457(18) 0.0462(5) Uani 1 1 d . . . . .
H14 H 0.8911 0.2393 0.8291 0.055 Uiso 1 1 calc R U . . .
C15 C 0.9223(2) 0.30892(12) 0.69910(19) 0.0492(5) Uani 1 1 d . . . . .
H15 H 1.0321 0.3200 0.7184 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8471(2) 0.34083(12) 0.60546(18) 0.0466(5) Uani 1 1 d . . . . .
H16 H 0.9046 0.3744 0.5609 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6875(2) 0.32387(11) 0.57642(16) 0.0392(4) Uani 1 1 d . . . . .
H17 H 0.6360 0.3461 0.5120 0.047 Uiso 1 1 calc R U . . .
C18 C 0.31338(18) 0.31710(9) 0.51819(14) 0.0269(4) Uani 1 1 d . . . . .
C19 C 0.2837(2) 0.38526(10) 0.57199(15) 0.0351(4) Uani 1 1 d . . . . .
H19 H 0.3123 0.3902 0.6490 0.042 Uiso 1 1 calc R U . . .
C20 C 0.2134(2) 0.44564(11) 0.51473(17) 0.0401(5) Uani 1 1 d . . . . .
H20 H 0.1968 0.4921 0.5521 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1671(2) 0.43891(11) 0.40330(16) 0.0392(4) Uani 1 1 d . . . . .
H21 H 0.1172 0.4802 0.3641 0.047 Uiso 1 1 calc R U . . .
C22 C 0.1942(2) 0.37163(11) 0.34986(15) 0.0381(4) Uani 1 1 d . . . . .
H22 H 0.1618 0.3666 0.2735 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2680(2) 0.31127(10) 0.40572(14) 0.0320(4) Uani 1 1 d . . . . .
H23 H 0.2877 0.2656 0.3671 0.038 Uiso 1 1 calc R U . . .


_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.
;

# MOLECULAR GEOMETRY

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
P1 C18 1.8294(17) . ?
P1 C1 1.8301(17) . ?
P1 C12 1.8358(17) . ?
C1 C2 1.347(2) . ?
C1 C8 1.487(2) . ?
C2 C3 1.488(2) . ?
C2 H2 0.9500 . ?
C3 C9 1.498(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.385(2) . ?
C4 C5 1.390(2) . ?
C4 C10 1.502(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(2) . ?
C7 C11 1.507(2) . ?
C8 C9 1.410(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.391(2) . ?
C12 C17 1.392(2) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.392(2) . ?
C18 C19 1.396(2) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C23 H23 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
C18 P1 C1 103.59(7) . . ?
C18 P1 C12 101.82(8) . . ?
C1 P1 C12 99.36(7) . . ?
C2 C1 C8 107.76(14) . . ?
C2 C1 P1 124.55(13) . . ?
C8 C1 P1 127.37(11) . . ?
C1 C2 C3 112.59(15) . . ?
C1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C2 C3 C9 102.55(13) . . ?
C2 C3 H3A 111.3 . . ?
C9 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C9 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C9 C4 C5 116.68(15) . . ?
C9 C4 C10 120.75(16) . . ?
C5 C4 C10 122.56(17) . . ?
C6 C5 C4 121.14(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 122.76(16) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C6 C7 C8 116.77(15) . . ?
C6 C7 C11 119.67(15) . . ?
C8 C7 C11 123.56(15) . . ?
C7 C8 C9 119.71(15) . . ?
C7 C8 C1 132.55(15) . . ?
C9 C8 C1 107.74(13) . . ?
C4 C9 C8 122.93(15) . . ?
C4 C9 C3 127.72(15) . . ?
C8 C9 C3 109.34(14) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.48(16) . . ?
C13 C12 P1 116.57(13) . . ?
C17 C12 P1 124.76(14) . . ?
C14 C13 C12 120.67(19) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.04(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.21(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.95(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.59(18) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C23 C18 C19 118.24(16) . . ?
C23 C18 P1 124.53(13) . . ?
C19 C18 P1 117.11(13) . . ?
C20 C19 C18 120.84(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.40(17) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.15(18) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 121.01(17) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 120.34(16) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?

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
C18 P1 C1 C2 105.46(15) . . . . ?
C12 P1 C1 C2 0.78(16) . . . . ?
C18 P1 C1 C8 -81.79(15) . . . . ?
C12 P1 C1 C8 173.53(14) . . . . ?
C8 C1 C2 C3 0.58(19) . . . . ?
P1 C1 C2 C3 174.53(12) . . . . ?
C1 C2 C3 C9 0.41(19) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C10 C4 C5 C6 -178.57(17) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C11 179.79(16) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C11 C7 C8 C9 179.23(15) . . . . ?
C6 C7 C8 C1 -179.80(16) . . . . ?
C11 C7 C8 C1 -0.4(3) . . . . ?
C2 C1 C8 C7 178.27(17) . . . . ?
P1 C1 C8 C7 4.5(3) . . . . ?
C2 C1 C8 C9 -1.41(18) . . . . ?
P1 C1 C8 C9 -175.14(12) . . . . ?
C5 C4 C9 C8 -1.1(2) . . . . ?
C10 C4 C9 C8 177.62(15) . . . . ?
C5 C4 C9 C3 177.93(16) . . . . ?
C10 C4 C9 C3 -3.4(3) . . . . ?
C7 C8 C9 C4 1.1(2) . . . . ?
C1 C8 C9 C4 -179.14(15) . . . . ?
C7 C8 C9 C3 -178.05(14) . . . . ?
C1 C8 C9 C3 1.68(18) . . . . ?
C2 C3 C9 C4 179.57(16) . . . . ?
C2 C3 C9 C8 -1.30(18) . . . . ?
C18 P1 C12 C13 156.43(13) . . . . ?
C1 P1 C12 C13 -97.44(14) . . . . ?
C18 P1 C12 C17 -28.66(17) . . . . ?
C1 P1 C12 C17 77.48(17) . . . . ?
C17 C12 C13 C14 -2.7(3) . . . . ?
P1 C12 C13 C14 172.53(14) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 1.9(3) . . . . ?
P1 C12 C17 C16 -172.90(15) . . . . ?
C1 P1 C18 C23 12.16(15) . . . . ?
C12 P1 C18 C23 114.96(14) . . . . ?
C1 P1 C18 C19 -171.84(12) . . . . ?
C12 P1 C18 C19 -69.04(14) . . . . ?
C23 C18 C19 C20 -0.9(2) . . . . ?
P1 C18 C19 C20 -177.21(14) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C18 1.3(3) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
P1 C18 C23 C22 175.40(13) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.046

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mb42
_database_code_depnum_ccdc_archive 'CCDC 1410416'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2013 template'

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 P'
_chemical_formula_sum            'C24 H23 P'
_chemical_formula_weight         342.39

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# Crystal Data

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.6549(2)
_cell_length_b                   11.23230(10)
_cell_length_c                   20.2304(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4639(4)
_cell_angle_gamma                90
_cell_volume                     3760.50(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   0.6989
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS v2008/1 (Apex2, Bruker AXS)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontal mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27446
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.191
_diffrn_reflns_theta_max         27.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4206
_reflns_number_gt                3857
_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 software package v2008 (Bruker AXS)
;
_computing_cell_refinement       
; Saint V7.68A and SADABS V2008/1 (Apex2, v2008; Bruker AXS)
;
_computing_data_reduction        
; Saint V7.68A and SADABS V2008/1 (Apex2, v2008; Bruker AXS
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2012)'
_computing_molecular_graphics    
; XP (SHELXTL-NT v6.14, Bruker AXS)
;

# REFINEMENT DATA

_refine_special_details          
;Refinement of F² against ALL reflections. The weighted R-
  factor   wR and goodness of fit S are based on F², 
  conventional   R-factors R are based on F, with 
  F set to zero   for negative F². The threshold expression
  of F² > σ(F²) is used only for calculating R-
  factors(gt) etc. and is not relevant to the choice of reflections
  for refinement.   R-factors based on F² are statistically
  about twice as large as those based on F, and R- factors 
  based on ALL data will be even larger.
  The non-hydrogen atoms were refined anisotropically. Hydrogen atoms of the
  phenyl- and CH₃-groups were included at geometrically idealized positions
  (C-H bond distances 0.95/0.99 ) and were not refined. 
  The isotropicthermal parameters of these hydrogen atoms were fixed
  at 1.2 (phenyl groups) and 1.5 times (CH₃-groups) that of
  the preceding carbon atom, respectively.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0544P)²+2.2679P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4206
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.18659(2) 0.03965(3) 0.01954(2) 0.02617(10) Uani 1 1 d . . . . .
C1 C 0.13579(7) 0.16546(10) 0.04118(6) 0.0275(2) Uani 1 1 d . . . . .
C2 C 0.07190(7) 0.21550(10) -0.00410(6) 0.0294(2) Uani 1 1 d . . . . .
H2 H 0.0577 0.1899 -0.0486 0.035 Uiso 1 1 calc R U . . .
C3 C 0.03460(7) 0.30553(11) 0.02637(6) 0.0303(2) Uani 1 1 d . . . . .
H3 H -0.0090 0.3526 0.0066 0.036 Uiso 1 1 calc R U . . .
C4 C 0.05487(7) 0.39395(11) 0.14431(6) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.10105(8) 0.38370(12) 0.20516(6) 0.0384(3) Uani 1 1 d . . . . .
H5 H 0.0908 0.4353 0.2405 0.046 Uiso 1 1 calc R U . . .
C6 C 0.16264(8) 0.29874(12) 0.21574(6) 0.0364(3) Uani 1 1 d . . . . .
H6 H 0.1929 0.2944 0.2584 0.044 Uiso 1 1 calc R U . . .
C7 C 0.18146(7) 0.22076(11) 0.16680(6) 0.0307(2) Uani 1 1 d . . . . .
C8 C 0.13567(7) 0.22918(10) 0.10338(5) 0.0271(2) Uani 1 1 d . . . . .
C9 C 0.07243(7) 0.31665(10) 0.09293(6) 0.0287(2) Uani 1 1 d . . . . .
C10 C -0.01481(9) 0.47988(13) 0.13271(7) 0.0442(3) Uani 1 1 d . . . . .
H10A H -0.0091 0.5276 0.0930 0.066 Uiso 1 1 calc R U . . .
H10B H -0.0150 0.5326 0.1713 0.066 Uiso 1 1 calc R U . . .
H10C H -0.0657 0.4354 0.1263 0.066 Uiso 1 1 calc R U . . .
C11 C 0.24992(8) 0.13397(12) 0.18260(6) 0.0382(3) Uani 1 1 d . . . . .
H11A H 0.2330 0.0548 0.1662 0.057 Uiso 1 1 calc R U . . .
H11B H 0.2645 0.1306 0.2309 0.057 Uiso 1 1 calc R U . . .
H11C H 0.2967 0.1601 0.1611 0.057 Uiso 1 1 calc R U . . .
C12 C 0.29478(7) 0.05256(12) 0.02218(7) 0.0370(3) Uani 1 1 d . . . . .
H12A H 0.3166 -0.0199 0.0039 0.056 Uiso 1 1 calc R U . . .
H12B H 0.3186 0.0631 0.0684 0.056 Uiso 1 1 calc R U . . .
H12C H 0.3080 0.1214 -0.0043 0.056 Uiso 1 1 calc R U . . .
C13 C 0.15210(7) 0.00355(10) -0.06581(5) 0.0273(2) Uani 1 1 d . . . . .
C14 C 0.18165(7) 0.06976(11) -0.11634(6) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.2197 0.1317 -0.1054 0.040 Uiso 1 1 calc R U . . .
C15 C 0.15547(8) 0.04495(11) -0.18238(6) 0.0363(3) Uani 1 1 d . . . . .
H15 H 0.1749 0.0909 -0.2166 0.044 Uiso 1 1 calc R U . . .
C16 C 0.10104(8) -0.04655(11) -0.19862(6) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.0837 -0.0638 -0.2440 0.042 Uiso 1 1 calc R U . . .
C17 C 0.07184(7) -0.11298(12) -0.14878(6) 0.0354(3) Uani 1 1 d . . . . .
H17 H 0.0345 -0.1756 -0.1600 0.042 Uiso 1 1 calc R U . . .
C18 C 0.09710(7) -0.08815(11) -0.08228(6) 0.0311(2) Uani 1 1 d . . . . .
H18 H 0.0769 -0.1336 -0.0482 0.037 Uiso 1 1 calc R U . . .
C19 C 0.16694(7) -0.08720(10) 0.07049(5) 0.0278(2) Uani 1 1 d . . . . .
C20 C 0.21818(8) -0.18567(12) 0.07700(6) 0.0373(3) Uani 1 1 d . . . . .
H20 H 0.2653 -0.1874 0.0545 0.045 Uiso 1 1 calc R U . . .
C21 C 0.20038(10) -0.28107(12) 0.11628(7) 0.0444(3) Uani 1 1 d . . . . .
H21 H 0.2352 -0.3483 0.1206 0.053 Uiso 1 1 calc R U . . .
C22 C 0.13199(9) -0.27870(12) 0.14927(7) 0.0428(3) Uani 1 1 d . . . . .
H22 H 0.1196 -0.3447 0.1757 0.051 Uiso 1 1 calc R U . . .
C23 C 0.08166(8) -0.18068(13) 0.14391(7) 0.0403(3) Uani 1 1 d . . . . .
H23 H 0.0352 -0.1788 0.1672 0.048 Uiso 1 1 calc R U . . .
C24 C 0.09894(7) -0.08467(11) 0.10441(6) 0.0332(3) Uani 1 1 d . . . . .
H24 H 0.0642 -0.0173 0.1006 0.040 Uiso 1 1 calc R U . . .


_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.
;

# MOLECULAR GEOMETRY

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
P1 C1 1.7285(12) . ?
P1 C12 1.8024(12) . ?
P1 C13 1.8034(11) . ?
P1 C19 1.8099(11) . ?
C1 C2 1.4380(15) . ?
C1 C8 1.4477(16) . ?
C2 C3 1.3692(17) . ?
C2 H2 0.9500 . ?
C3 C9 1.4265(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3809(18) . ?
C4 C9 1.4100(17) . ?
C4 C10 1.5074(18) . ?
C5 C6 1.3998(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3840(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4200(16) . ?
C7 C11 1.5068(17) . ?
C8 C9 1.4385(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.3937(16) . ?
C13 C14 1.3978(16) . ?
C14 C15 1.3861(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3852(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3859(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3918(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3891(16) . ?
C19 C20 1.3942(17) . ?
C20 C21 1.3858(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3914(17) . ?
C23 H23 0.9500 . ?
C24 H24 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
C1 P1 C12 116.29(6) . . ?
C1 P1 C13 108.30(5) . . ?
C12 P1 C13 104.84(6) . . ?
C1 P1 C19 111.98(5) . . ?
C12 P1 C19 106.90(6) . . ?
C13 P1 C19 108.04(5) . . ?
C2 C1 C8 106.68(10) . . ?
C2 C1 P1 120.43(9) . . ?
C8 C1 P1 132.29(9) . . ?
C3 C2 C1 110.04(10) . . ?
C3 C2 H2 125.0 . . ?
C1 C2 H2 125.0 . . ?
C2 C3 C9 108.36(10) . . ?
C2 C3 H3 125.8 . . ?
C9 C3 H3 125.8 . . ?
C5 C4 C9 117.70(11) . . ?
C5 C4 C10 122.27(12) . . ?
C9 C4 C10 119.97(12) . . ?
C4 C5 C6 121.20(12) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 122.90(11) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 117.54(11) . . ?
C6 C7 C11 118.98(11) . . ?
C8 C7 C11 123.46(11) . . ?
C7 C8 C9 119.21(11) . . ?
C7 C8 C1 134.37(11) . . ?
C9 C8 C1 106.42(10) . . ?
C4 C9 C3 130.06(11) . . ?
C4 C9 C8 121.43(11) . . ?
C3 C9 C8 108.49(10) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
P1 C12 H12A 109.5 . . ?
P1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
P1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.63(11) . . ?
C18 C13 P1 121.67(9) . . ?
C14 C13 P1 118.70(9) . . ?
C15 C14 C13 119.97(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.28(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.05(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.19(11) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 119.88(11) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C24 C19 C20 119.61(11) . . ?
C24 C19 P1 118.36(9) . . ?
C20 C19 P1 122.03(9) . . ?
C21 C20 C19 119.96(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.17(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.19(12) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.02(13) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.04(12) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?

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
C12 P1 C1 C2 123.68(9) . . . . ?
C13 P1 C1 C2 6.01(10) . . . . ?
C19 P1 C1 C2 -113.02(9) . . . . ?
C12 P1 C1 C8 -66.50(12) . . . . ?
C13 P1 C1 C8 175.83(10) . . . . ?
C19 P1 C1 C8 56.80(12) . . . . ?
C8 C1 C2 C3 0.89(12) . . . . ?
P1 C1 C2 C3 173.04(8) . . . . ?
C1 C2 C3 C9 -0.54(13) . . . . ?
C9 C4 C5 C6 -0.64(18) . . . . ?
C10 C4 C5 C6 176.48(12) . . . . ?
C4 C5 C6 C7 0.25(19) . . . . ?
C5 C6 C7 C8 0.23(18) . . . . ?
C5 C6 C7 C11 178.83(12) . . . . ?
C6 C7 C8 C9 -0.28(15) . . . . ?
C11 C7 C8 C9 -178.82(10) . . . . ?
C6 C7 C8 C1 -179.28(12) . . . . ?
C11 C7 C8 C1 2.2(2) . . . . ?
C2 C1 C8 C7 178.21(12) . . . . ?
P1 C1 C8 C7 7.4(2) . . . . ?
C2 C1 C8 C9 -0.87(11) . . . . ?
P1 C1 C8 C9 -171.72(9) . . . . ?
C5 C4 C9 C3 178.79(11) . . . . ?
C10 C4 C9 C3 1.61(18) . . . . ?
C5 C4 C9 C8 0.57(16) . . . . ?
C10 C4 C9 C8 -176.61(11) . . . . ?
C2 C3 C9 C4 -178.43(11) . . . . ?
C2 C3 C9 C8 -0.03(12) . . . . ?
C7 C8 C9 C4 -0.12(16) . . . . ?
C1 C8 C9 C4 179.14(10) . . . . ?
C7 C8 C9 C3 -178.68(10) . . . . ?
C1 C8 C9 C3 0.57(12) . . . . ?
C1 P1 C13 C18 -102.33(10) . . . . ?
C12 P1 C13 C18 132.90(10) . . . . ?
C19 P1 C13 C18 19.16(11) . . . . ?
C1 P1 C13 C14 77.67(11) . . . . ?
C12 P1 C13 C14 -47.10(11) . . . . ?
C19 P1 C13 C14 -160.84(10) . . . . ?
C18 C13 C14 C15 0.77(19) . . . . ?
P1 C13 C14 C15 -179.23(10) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C18 -0.06(19) . . . . ?
C16 C17 C18 C13 -0.19(19) . . . . ?
C14 C13 C18 C17 -0.16(18) . . . . ?
P1 C13 C18 C17 179.84(9) . . . . ?
C1 P1 C19 C24 19.48(11) . . . . ?
C12 P1 C19 C24 147.94(10) . . . . ?
C13 P1 C19 C24 -99.70(10) . . . . ?
C1 P1 C19 C20 -159.84(10) . . . . ?
C12 P1 C19 C20 -31.39(12) . . . . ?
C13 P1 C19 C20 80.97(11) . . . . ?
C24 C19 C20 C21 1.06(19) . . . . ?
P1 C19 C20 C21 -179.62(10) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C20 C21 C22 C23 -0.8(2) . . . . ?
C21 C22 C23 C24 1.0(2) . . . . ?
C20 C19 C24 C23 -0.86(18) . . . . ?
P1 C19 C24 C23 179.80(9) . . . . ?
C22 C23 C24 C19 -0.17(19) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.046

_shelxl_version_number           2012-9

