# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_SNAPFMe2
_database_code_depnum_ccdc_archive 'CCDC 1553533'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
?
;
_chemical_name_common            SNAPF-Me2
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 O3 P'
_chemical_formula_sum            'C31 H23 O3 P'
_chemical_formula_weight         474.46

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'
O O 0.0106 0.0060 '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'

_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                   9.7350(7)
_cell_length_b                   15.9966(9)
_cell_length_c                   15.9748(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.392(4)
_cell_angle_gamma                90
_cell_volume                     2398.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Single Crystal X-ray diffractometer equipped with 
FR-X generator, Varimax optics, and PILATUS 200K photon 
counting detector
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31735
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5501
_reflns_number_gt                4837
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0431P)²+1.3772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5501
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
P1 P 0.84773(3) 0.15500(2) 0.65660(2) 0.01472(8) Uani 1 1 d . . . . .
C1 C 0.66985(14) 0.28535(8) 0.65863(9) 0.0213(3) Uani 1 1 d . . . . .
H1 H 0.7314 0.3144 0.6314 0.026 Uiso 1 1 calc R U . . .
C2 C 0.55285(14) 0.33107(8) 0.68019(10) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.47214(14) 0.28459(8) 0.72984(10) 0.0243(3) Uani 1 1 d . . . . .
H2 H 0.4013 0.3128 0.7501 0.029 Uiso 1 1 calc R U . . .
C4 C 0.49548(14) 0.20271(8) 0.74772(9) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.4418 0.1752 0.7813 0.025 Uiso 1 1 calc R U . . .
C5 C 0.60025(13) 0.06862(8) 0.72081(8) 0.0167(2) Uani 1 1 d . . . . .
C6 C 0.64954(13) -0.06862(8) 0.66356(8) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.5752 -0.0911 0.6850 0.022 Uiso 1 1 calc R U . . .
C7 C 0.67173(14) -0.20449(8) 0.59340(9) 0.0222(3) Uani 1 1 d . . . . .
H5 H 0.5933 -0.2264 0.6112 0.027 Uiso 1 1 calc R U . . .
C8 C 0.73772(15) -0.25293(8) 0.54501(9) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.7022 -0.3073 0.5275 0.028 Uiso 1 1 calc R U . . .
C9 C 0.85876(14) -0.22268(8) 0.52077(8) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.90969(13) -0.14315(8) 0.54434(8) 0.0179(2) Uani 1 1 d . . . . .
H7 H 0.9925 -0.1237 0.5296 0.021 Uiso 1 1 calc R U . . .
C11 C 0.87585(13) -0.00507(7) 0.60682(8) 0.0161(2) Uani 1 1 d . . . . .
H8 H 0.9545 0.0169 0.5893 0.019 Uiso 1 1 calc R U . . .
C12 C 0.69234(13) 0.20281(8) 0.67665(8) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.59998(13) 0.15490(8) 0.71742(8) 0.0166(2) Uani 1 1 d . . . . .
C14 C 0.68544(13) 0.01507(8) 0.67887(8) 0.0158(2) Uani 1 1 d . . . . .
C15 C 0.80091(13) 0.04655(7) 0.64739(8) 0.0154(2) Uani 1 1 d . . . . .
C16 C 0.71959(13) -0.12151(8) 0.61730(8) 0.0176(2) Uani 1 1 d . . . . .
C17 C 0.83848(13) -0.09079(8) 0.59036(8) 0.0163(2) Uani 1 1 d . . . . .
C18 C 0.98746(13) 0.16860(8) 0.75509(8) 0.0179(2) Uani 1 1 d . . . . .
C19 C 1.00689(16) 0.11123(9) 0.82302(10) 0.0269(3) Uani 1 1 d . . . . .
H9 H 0.9503 0.0621 0.8163 0.032 Uiso 1 1 calc R U . . .
C20 C 1.10945(18) 0.12625(11) 0.90067(11) 0.0378(4) Uani 1 1 d . . . . .
H10 H 1.1217 0.0877 0.9473 0.045 Uiso 1 1 calc R U . . .
C21 C 1.19385(17) 0.19739(12) 0.91009(11) 0.0382(4) Uani 1 1 d . . . . .
H11 H 1.2640 0.2072 0.9631 0.046 Uiso 1 1 calc R U . . .
C22 C 1.17614(16) 0.25433(11) 0.84223(10) 0.0344(4) Uani 1 1 d . . . . .
H12 H 1.2346 0.3028 0.8490 0.041 Uiso 1 1 calc R U . . .
C23 C 1.07313(15) 0.24053(9) 0.76460(9) 0.0263(3) Uani 1 1 d . . . . .
H13 H 1.0607 0.2795 0.7183 0.032 Uiso 1 1 calc R U . . .
O1 O 0.88678(10) 0.19072(6) 0.57952(6) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.52688(12) 0.40489(6) 0.65831(9) 0.0378(3) Uani 1 1 d . . . . .
O3 O 0.91679(11) -0.27504(6) 0.47320(7) 0.0272(2) Uani 1 1 d . . . . .
H14 H 0.9766 -0.2489 0.4538 0.041 Uiso 1 1 calc R U . . .
C24 C 0.50108(13) 0.02453(7) 0.76387(8) 0.0164(2) Uani 1 1 d . . . . .
C25 C 0.55304(14) -0.00238(8) 0.85048(8) 0.0183(2) Uani 1 1 d . . . . .
C26 C 0.46100(15) -0.04483(8) 0.88932(9) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.4955 -0.0647 0.9472 0.028 Uiso 1 1 calc R U . . .
C27 C 0.31998(15) -0.05853(9) 0.84490(9) 0.0256(3) Uani 1 1 d . . . . .
H16 H 0.2583 -0.0869 0.8725 0.031 Uiso 1 1 calc R U . . .
C28 C 0.26905(15) -0.03069(9) 0.76002(9) 0.0250(3) Uani 1 1 d . . . . .
H17 H 0.1719 -0.0394 0.7302 0.030 Uiso 1 1 calc R U . . .
C29 C 0.35890(14) 0.00997(8) 0.71795(9) 0.0213(3) Uani 1 1 d . . . . .
C30 C 0.70478(15) 0.01480(9) 0.90096(9) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.7143 0.0068 0.9631 0.037 Uiso 1 1 calc R U . . .
H19 H 0.7298 0.0725 0.8906 0.037 Uiso 1 1 calc R U . . .
H20 H 0.7688 -0.0238 0.8820 0.037 Uiso 1 1 calc R U . . .
C31 C 0.30133(17) 0.03834(12) 0.62521(10) 0.0368(4) Uani 1 1 d . . . . .
H21 H 0.2165 0.0056 0.5974 0.055 Uiso 1 1 calc R U . . .
H22 H 0.3741 0.0302 0.5937 0.055 Uiso 1 1 calc R U . . .
H23 H 0.2761 0.0977 0.6242 0.055 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.
;

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 O1 1.4953(9) . ?
P1 C15 1.7898(12) . ?
P1 C12 1.7980(12) . ?
P1 C18 1.7992(13) . ?
C1 C12 1.3567(17) . ?
C1 C2 1.4694(18) . ?
C2 O2 1.2385(17) . ?
C2 C3 1.4594(19) . ?
C3 C4 1.3470(19) . ?
C4 C13 1.4546(17) . ?
C5 C13 1.3812(17) . ?
C5 C14 1.4716(16) . ?
C5 C24 1.5017(16) . ?
C6 C14 1.3887(17) . ?
C6 C16 1.4123(17) . ?
C7 C8 1.3690(18) . ?
C7 C16 1.4249(17) . ?
C8 C9 1.4194(18) . ?
C9 O3 1.3513(15) . ?
C9 C10 1.3809(17) . ?
C10 C17 1.4118(17) . ?
C11 C15 1.3730(16) . ?
C11 C17 1.4250(17) . ?
C12 C13 1.4598(17) . ?
C14 C15 1.4388(16) . ?
C16 C17 1.4251(17) . ?
C18 C19 1.3952(19) . ?
C18 C23 1.4055(18) . ?
C19 C20 1.391(2) . ?
C20 C21 1.388(2) . ?
C21 C22 1.391(3) . ?
C22 C23 1.390(2) . ?
C24 C29 1.4033(18) . ?
C24 C25 1.4085(17) . ?
C25 C26 1.3944(18) . ?
C25 C30 1.5085(18) . ?
C26 C27 1.385(2) . ?
C27 C28 1.388(2) . ?
C28 C29 1.3971(18) . ?
C29 C31 1.5079(19) . ?

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
O1 P1 C15 114.68(6) . . ?
O1 P1 C12 113.20(6) . . ?
C15 P1 C12 102.65(6) . . ?
O1 P1 C18 112.05(6) . . ?
C15 P1 C18 107.83(6) . . ?
C12 P1 C18 105.62(6) . . ?
C12 C1 C2 121.75(12) . . ?
O2 C2 C3 122.69(12) . . ?
O2 C2 C1 121.42(13) . . ?
C3 C2 C1 115.88(11) . . ?
C4 C3 C2 121.72(12) . . ?
C3 C4 C13 122.30(12) . . ?
C13 C5 C14 124.00(11) . . ?
C13 C5 C24 119.50(11) . . ?
C14 C5 C24 116.34(10) . . ?
C14 C6 C16 122.39(11) . . ?
C8 C7 C16 120.63(12) . . ?
C7 C8 C9 120.60(12) . . ?
O3 C9 C10 123.43(12) . . ?
O3 C9 C8 116.31(11) . . ?
C10 C9 C8 120.25(12) . . ?
C9 C10 C17 119.88(12) . . ?
C15 C11 C17 121.61(11) . . ?
C1 C12 C13 121.45(11) . . ?
C1 C12 P1 118.18(10) . . ?
C13 C12 P1 120.21(9) . . ?
C5 C13 C4 120.44(11) . . ?
C5 C13 C12 123.17(11) . . ?
C4 C13 C12 116.13(11) . . ?
C6 C14 C15 117.34(11) . . ?
C6 C14 C5 119.70(11) . . ?
C15 C14 C5 122.85(11) . . ?
C11 C15 C14 121.12(11) . . ?
C11 C15 P1 117.78(9) . . ?
C14 C15 P1 121.07(9) . . ?
C6 C16 C7 121.96(11) . . ?
C6 C16 C17 119.67(11) . . ?
C7 C16 C17 118.32(11) . . ?
C10 C17 C11 122.03(11) . . ?
C10 C17 C16 120.20(11) . . ?
C11 C17 C16 117.66(11) . . ?
C19 C18 C23 120.02(12) . . ?
C19 C18 P1 121.03(10) . . ?
C23 C18 P1 118.87(10) . . ?
C20 C19 C18 119.80(14) . . ?
C21 C20 C19 120.14(15) . . ?
C20 C21 C22 120.33(14) . . ?
C23 C22 C21 120.14(14) . . ?
C22 C23 C18 119.56(14) . . ?
C29 C24 C25 120.67(11) . . ?
C29 C24 C5 120.22(11) . . ?
C25 C24 C5 119.11(11) . . ?
C26 C25 C24 118.70(12) . . ?
C26 C25 C30 120.30(12) . . ?
C24 C25 C30 120.99(11) . . ?
C27 C26 C25 121.03(12) . . ?
C26 C27 C28 119.89(12) . . ?
C27 C28 C29 120.83(13) . . ?
C28 C29 C24 118.83(12) . . ?
C28 C29 C31 119.73(13) . . ?
C24 C29 C31 121.43(12) . . ?

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 C1 C2 O2 -175.00(14) . . . . ?
C12 C1 C2 C3 6.0(2) . . . . ?
O2 C2 C3 C4 175.24(15) . . . . ?
C1 C2 C3 C4 -5.8(2) . . . . ?
C2 C3 C4 C13 -1.3(2) . . . . ?
C16 C7 C8 C9 2.6(2) . . . . ?
C7 C8 C9 O3 179.85(13) . . . . ?
C7 C8 C9 C10 -1.3(2) . . . . ?
O3 C9 C10 C17 176.76(12) . . . . ?
C8 C9 C10 C17 -1.98(19) . . . . ?
C2 C1 C12 C13 0.8(2) . . . . ?
C2 C1 C12 P1 -174.49(10) . . . . ?
O1 P1 C12 C1 -34.13(12) . . . . ?
C15 P1 C12 C1 -158.31(11) . . . . ?
C18 P1 C12 C1 88.82(11) . . . . ?
O1 P1 C12 C13 150.48(9) . . . . ?
C15 P1 C12 C13 26.30(11) . . . . ?
C18 P1 C12 C13 -86.56(11) . . . . ?
C14 C5 C13 C4 169.50(11) . . . . ?
C24 C5 C13 C4 -5.85(18) . . . . ?
C14 C5 C13 C12 -4.44(19) . . . . ?
C24 C5 C13 C12 -179.79(11) . . . . ?
C3 C4 C13 C5 -166.20(13) . . . . ?
C3 C4 C13 C12 8.15(19) . . . . ?
C1 C12 C13 C5 166.33(13) . . . . ?
P1 C12 C13 C5 -18.44(17) . . . . ?
C1 C12 C13 C4 -7.85(18) . . . . ?
P1 C12 C13 C4 167.38(9) . . . . ?
C16 C6 C14 C15 -1.51(18) . . . . ?
C16 C6 C14 C5 174.69(11) . . . . ?
C13 C5 C14 C6 -161.15(12) . . . . ?
C24 C5 C14 C6 14.34(17) . . . . ?
C13 C5 C14 C15 14.84(19) . . . . ?
C24 C5 C14 C15 -169.67(11) . . . . ?
C17 C11 C15 C14 3.09(18) . . . . ?
C17 C11 C15 P1 -174.88(9) . . . . ?
C6 C14 C15 C11 -2.43(18) . . . . ?
C5 C14 C15 C11 -178.51(11) . . . . ?
C6 C14 C15 P1 175.47(9) . . . . ?
C5 C14 C15 P1 -0.61(16) . . . . ?
O1 P1 C15 C11 37.64(12) . . . . ?
C12 P1 C15 C11 160.83(10) . . . . ?
C18 P1 C15 C11 -87.94(11) . . . . ?
O1 P1 C15 C14 -140.33(10) . . . . ?
C12 P1 C15 C14 -17.14(11) . . . . ?
C18 P1 C15 C14 94.09(10) . . . . ?
C14 C6 C16 C7 -172.75(12) . . . . ?
C14 C6 C16 C17 4.77(19) . . . . ?
C8 C7 C16 C6 176.89(13) . . . . ?
C8 C7 C16 C17 -0.7(2) . . . . ?
C9 C10 C17 C11 -172.10(12) . . . . ?
C9 C10 C17 C16 3.93(19) . . . . ?
C15 C11 C17 C10 176.32(12) . . . . ?
C15 C11 C17 C16 0.19(18) . . . . ?
C6 C16 C17 C10 179.78(11) . . . . ?
C7 C16 C17 C10 -2.61(18) . . . . ?
C6 C16 C17 C11 -4.01(18) . . . . ?
C7 C16 C17 C11 173.60(11) . . . . ?
O1 P1 C18 C19 -149.85(11) . . . . ?
C15 P1 C18 C19 -22.73(13) . . . . ?
C12 P1 C18 C19 86.47(12) . . . . ?
O1 P1 C18 C23 33.30(12) . . . . ?
C15 P1 C18 C23 160.42(10) . . . . ?
C12 P1 C18 C23 -90.38(11) . . . . ?
C23 C18 C19 C20 1.2(2) . . . . ?
P1 C18 C19 C20 -175.63(12) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C18 -0.2(2) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
P1 C18 C23 C22 176.33(11) . . . . ?
C13 C5 C24 C29 82.83(16) . . . . ?
C14 C5 C24 C29 -92.88(14) . . . . ?
C13 C5 C24 C25 -97.62(14) . . . . ?
C14 C5 C24 C25 86.68(14) . . . . ?
C29 C24 C25 C26 0.89(18) . . . . ?
C5 C24 C25 C26 -178.66(11) . . . . ?
C29 C24 C25 C30 -178.56(12) . . . . ?
C5 C24 C25 C30 1.89(17) . . . . ?
C24 C25 C26 C27 -1.75(19) . . . . ?
C30 C25 C26 C27 177.70(12) . . . . ?
C25 C26 C27 C28 0.8(2) . . . . ?
C26 C27 C28 C29 1.1(2) . . . . ?
C27 C28 C29 C24 -1.9(2) . . . . ?
C27 C28 C29 C31 179.01(14) . . . . ?
C25 C24 C29 C28 0.89(19) . . . . ?
C5 C24 C29 C28 -179.56(12) . . . . ?
C25 C24 C29 C31 179.98(13) . . . . ?
C5 C24 C29 C31 -0.5(2) . . . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cis6abMe
_database_code_depnum_ccdc_archive 'CCDC 1553531'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
3,7-dimethoxy-5-phenyl-10-(o-tolyl)-10H-acridophosphine 5-oxide 
;
_chemical_name_common            cis6abMe
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 O3 P'
_chemical_formula_sum            'C28 H25 O3 P'
_chemical_formula_weight         440.45

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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'

_cell_length_a                   9.230(10)
_cell_length_b                   26.54(3)
_cell_length_c                   9.263(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.736(18)
_cell_angle_gamma                90.00
_cell_volume                     2195(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2664
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      29.1

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku PILATUS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24050
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0970
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4981
_reflns_number_gt                2744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1732P)²+2.9643P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4981
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1675
_refine_ls_R_factor_gt           0.1174
_refine_ls_wR_factor_ref         0.3458
_refine_ls_wR_factor_gt          0.3070
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.01514(15) 0.11753(5) 0.71232(19) 0.0432(5) Uani 1 1 d . . .
O1 O 0.1580(4) 0.11769(14) 0.8311(5) 0.0624(13) Uani 1 1 d . . .
O2 O 0.2354(5) 0.23264(14) 0.3645(7) 0.0763(17) Uani 1 1 d . . .
O3 O -0.3019(4) -0.02048(12) 0.3845(4) 0.0365(8) Uani 1 1 d . . .
C1 C -0.0777(5) 0.05772(17) 0.6810(6) 0.0325(10) Uani 1 1 d . . .
C2 C -0.0811(5) 0.02935(18) 0.8062(6) 0.0383(11) Uani 1 1 d . . .
H2 H -0.0264 0.0403 0.9022 0.046 Uiso 1 1 calc R . .
C3 C -0.1637(6) -0.01494(18) 0.7921(6) 0.0392(12) Uani 1 1 d . . .
H3 H -0.1664 -0.0337 0.8787 0.047 Uiso 1 1 calc R . .
C4 C -0.2425(5) -0.03208(17) 0.6520(6) 0.0371(12) Uani 1 1 d . . .
H4 H -0.3012 -0.0619 0.6432 0.045 Uiso 1 1 calc R . .
C5 C -0.2347(5) -0.00523(15) 0.5248(5) 0.0292(10) Uani 1 1 d . . .
C6 C -0.1528(5) 0.04082(16) 0.5375(6) 0.0314(11) Uani 1 1 d . . .
C7 C 0.0343(5) 0.13590(17) 0.5310(7) 0.0443(14) Uani 1 1 d . . .
C8 C 0.1320(6) 0.17678(18) 0.5242(8) 0.0537(17) Uani 1 1 d . . .
H8 H 0.1869 0.1928 0.6130 0.064 Uiso 1 1 calc R . .
C9 C 0.1459(6) 0.19296(19) 0.3845(9) 0.059(2) Uani 1 1 d . . .
C10 C 0.0697(7) 0.16876(19) 0.2542(8) 0.0569(18) Uani 1 1 d . . .
H10 H 0.0813 0.1797 0.1602 0.068 Uiso 1 1 calc R . .
C11 C -0.0230(6) 0.12876(18) 0.2625(7) 0.0433(14) Uani 1 1 d . . .
H11 H -0.0748 0.1124 0.1731 0.052 Uiso 1 1 calc R . .
C12 C -0.0433(5) 0.11138(17) 0.4005(7) 0.0386(12) Uani 1 1 d . . .
C13 C -0.1529(5) 0.06767(15) 0.3912(6) 0.0325(11) Uani 1 1 d . . .
H13 H -0.1240 0.0418 0.3253 0.039 Uiso 1 1 calc R . .
C14 C -0.3104(5) 0.08646(16) 0.3078(6) 0.0317(11) Uani 1 1 d . . .
C15 C -0.3788(5) 0.12210(16) 0.3815(6) 0.0363(12) Uani 1 1 d . . .
H15 H -0.3290 0.1328 0.4795 0.044 Uiso 1 1 calc R . .
C16 C -0.5197(5) 0.14190(17) 0.3114(6) 0.0367(12) Uani 1 1 d . . .
H16 H -0.5654 0.1659 0.3617 0.044 Uiso 1 1 calc R . .
C17 C -0.5927(6) 0.12630(18) 0.1680(7) 0.0405(12) Uani 1 1 d . . .
H17 H -0.6881 0.1398 0.1201 0.049 Uiso 1 1 calc R . .
C18 C -0.5262(5) 0.09096(19) 0.0948(6) 0.0398(12) Uani 1 1 d . . .
H18 H -0.5777 0.0801 -0.0024 0.048 Uiso 1 1 calc R . .
C19 C -0.3841(6) 0.07089(17) 0.1619(6) 0.0370(11) Uani 1 1 d . . .
C20 C -0.3164(6) 0.0336(2) 0.0755(6) 0.0443(13) Uani 1 1 d . . .
H20A H -0.3898 0.0251 -0.0179 0.066 Uiso 1 1 calc R . .
H20B H -0.2880 0.0030 0.1352 0.066 Uiso 1 1 calc R . .
H20C H -0.2274 0.0483 0.0530 0.066 Uiso 1 1 calc R . .
C21 C -0.1232(6) 0.1596(2) 0.7599(7) 0.0459(13) Uani 1 1 d . . .
C24 C -0.3254(10) 0.2253(2) 0.8421(11) 0.092(3) Uani 1 1 d . . .
H24 H -0.3854 0.2479 0.8815 0.110 Uiso 1 1 calc R . .
C27 C 0.3130(11) 0.2592(3) 0.4923(12) 0.118(4) Uani 1 1 d . . .
H27A H 0.3616 0.2888 0.4621 0.177 Uiso 1 1 calc R . .
H27B H 0.3891 0.2372 0.5547 0.177 Uiso 1 1 calc R . .
H27C H 0.2423 0.2700 0.5491 0.177 Uiso 1 1 calc R . .
C28 C -0.4059(6) -0.06198(18) 0.3648(6) 0.0418(13) Uani 1 1 d . . .
H28A H -0.4384 -0.0708 0.2587 0.063 Uiso 1 1 calc R . .
H28B H -0.4932 -0.0522 0.4005 0.063 Uiso 1 1 calc R . .
H28C H -0.3569 -0.0911 0.4218 0.063 Uiso 1 1 calc R . .
C22A C -0.2467(9) 0.1412(2) 0.8090(10) 0.082(3) Uani 1 1 d . . .
H22A H -0.2605 0.1059 0.8153 0.098 Uiso 1 1 calc R . .
C23A C -0.3476(10) 0.1740(2) 0.8482(11) 0.091(3) Uani 1 1 d . . .
H23A H -0.4312 0.1612 0.8789 0.109 Uiso 1 1 calc R . .
C25A C -0.2188(10) 0.2432(2) 0.7805(13) 0.116(4) Uani 1 1 d . . .
H25A H -0.2110 0.2784 0.7664 0.140 Uiso 1 1 calc R . .
C26A C -0.1198(9) 0.2104(2) 0.7372(13) 0.112(4) Uani 1 1 d . . .
H26A H -0.0478 0.2238 0.6905 0.135 Uiso 1 1 calc R . .


_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
P1 O1 1.487(4) . ?
P1 C1 1.792(5) . ?
P1 C7 1.800(6) . ?
P1 C21 1.833(5) . ?
O2 C9 1.380(6) . ?
O2 C27 1.407(10) . ?
O3 C5 1.352(6) . ?
O3 C28 1.442(5) . ?
C1 C2 1.390(7) . ?
C1 C6 1.407(7) . ?
C2 C3 1.389(7) . ?
C3 C4 1.392(7) . ?
C4 C5 1.395(7) . ?
C5 C6 1.426(6) . ?
C6 C13 1.531(7) . ?
C7 C12 1.400(8) . ?
C7 C8 1.423(7) . ?
C8 C9 1.399(9) . ?
C9 C10 1.390(10) . ?
C10 C11 1.378(7) . ?
C11 C12 1.415(7) . ?
C12 C13 1.528(6) . ?
C13 C14 1.545(6) . ?
C14 C15 1.407(6) . ?
C14 C19 1.411(7) . ?
C15 C16 1.400(7) . ?
C16 C17 1.391(8) . ?
C17 C18 1.389(7) . ?
C18 C19 1.405(7) . ?
C19 C20 1.506(7) . ?
C21 C26A 1.366(8) . ?
C21 C22A 1.418(9) . ?
C24 C25A 1.343(9) . ?
C24 C23A 1.381(9) . ?
C22A C23A 1.389(9) . ?
C25A C26A 1.391(9) . ?

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
O1 P1 C1 114.8(2) . . ?
O1 P1 C7 114.2(3) . . ?
C1 P1 C7 104.2(2) . . ?
O1 P1 C21 111.2(3) . . ?
C1 P1 C21 104.2(2) . . ?
C7 P1 C21 107.4(2) . . ?
C9 O2 C27 117.6(6) . . ?
C5 O3 C28 118.6(4) . . ?
C2 C1 C6 120.3(4) . . ?
C2 C1 P1 117.1(4) . . ?
C6 C1 P1 122.4(4) . . ?
C3 C2 C1 120.6(5) . . ?
C2 C3 C4 120.5(5) . . ?
C3 C4 C5 119.5(4) . . ?
O3 C5 C4 123.3(4) . . ?
O3 C5 C6 116.1(4) . . ?
C4 C5 C6 120.6(4) . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 C13 125.2(4) . . ?
C5 C6 C13 116.4(4) . . ?
C12 C7 C8 120.5(6) . . ?
C12 C7 P1 122.0(4) . . ?
C8 C7 P1 117.5(5) . . ?
C9 C8 C7 118.9(6) . . ?
O2 C9 C10 115.1(6) . . ?
O2 C9 C8 123.9(7) . . ?
C10 C9 C8 121.0(5) . . ?
C11 C10 C9 119.5(6) . . ?
C10 C11 C12 121.9(6) . . ?
C7 C12 C11 118.2(4) . . ?
C7 C12 C13 126.0(5) . . ?
C11 C12 C13 115.8(5) . . ?
C12 C13 C6 116.9(4) . . ?
C12 C13 C14 108.0(3) . . ?
C6 C13 C14 112.4(3) . . ?
C15 C14 C19 119.7(5) . . ?
C15 C14 C13 117.1(5) . . ?
C19 C14 C13 123.2(4) . . ?
C16 C15 C14 120.4(5) . . ?
C17 C16 C15 119.9(5) . . ?
C18 C17 C16 120.0(5) . . ?
C17 C18 C19 121.3(5) . . ?
C18 C19 C14 118.7(5) . . ?
C18 C19 C20 118.8(5) . . ?
C14 C19 C20 122.5(5) . . ?
C26A C21 C22A 116.2(5) . . ?
C26A C21 P1 121.4(5) . . ?
C22A C21 P1 122.2(4) . . ?
C25A C24 C23A 119.9(6) . . ?
C23A C22A C21 121.0(6) . . ?
C24 C23A C22A 119.4(7) . . ?
C24 C25A C26A 120.5(6) . . ?
C21 C26A C25A 122.0(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
O1 P1 C1 C2 41.7(4) . . . . ?
C7 P1 C1 C2 167.3(4) . . . . ?
C21 P1 C1 C2 -80.2(4) . . . . ?
O1 P1 C1 C6 -142.3(4) . . . . ?
C7 P1 C1 C6 -16.6(4) . . . . ?
C21 P1 C1 C6 95.9(4) . . . . ?
C6 C1 C2 C3 -2.7(7) . . . . ?
P1 C1 C2 C3 173.4(4) . . . . ?
C1 C2 C3 C4 1.1(7) . . . . ?
C2 C3 C4 C5 1.9(7) . . . . ?
C28 O3 C5 C4 10.1(6) . . . . ?
C28 O3 C5 C6 -169.9(4) . . . . ?
C3 C4 C5 O3 176.8(4) . . . . ?
C3 C4 C5 C6 -3.1(7) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
P1 C1 C6 C5 -174.5(3) . . . . ?
C2 C1 C6 C13 -177.8(4) . . . . ?
P1 C1 C6 C13 6.3(6) . . . . ?
O3 C5 C6 C1 -178.5(4) . . . . ?
C4 C5 C6 C1 1.4(6) . . . . ?
O3 C5 C6 C13 0.8(5) . . . . ?
C4 C5 C6 C13 -179.2(4) . . . . ?
O1 P1 C7 C12 139.2(4) . . . . ?
C1 P1 C7 C12 13.2(4) . . . . ?
C21 P1 C7 C12 -97.0(4) . . . . ?
O1 P1 C7 C8 -40.9(4) . . . . ?
C1 P1 C7 C8 -166.9(4) . . . . ?
C21 P1 C7 C8 82.9(4) . . . . ?
C12 C7 C8 C9 1.8(7) . . . . ?
P1 C7 C8 C9 -178.1(4) . . . . ?
C27 O2 C9 C10 178.8(6) . . . . ?
C27 O2 C9 C8 -2.1(8) . . . . ?
C7 C8 C9 O2 179.0(4) . . . . ?
C7 C8 C9 C10 -2.0(8) . . . . ?
O2 C9 C10 C11 -179.8(4) . . . . ?
C8 C9 C10 C11 1.1(8) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C8 C7 C12 C11 -0.7(7) . . . . ?
P1 C7 C12 C11 179.2(3) . . . . ?
C8 C7 C12 C13 -179.1(4) . . . . ?
P1 C7 C12 C13 0.8(6) . . . . ?
C10 C11 C12 C7 -0.2(7) . . . . ?
C10 C11 C12 C13 178.3(4) . . . . ?
C7 C12 C13 C6 -14.2(6) . . . . ?
C11 C12 C13 C6 167.5(4) . . . . ?
C7 C12 C13 C14 113.8(5) . . . . ?
C11 C12 C13 C14 -64.6(5) . . . . ?
C1 C6 C13 C12 10.3(6) . . . . ?
C5 C6 C13 C12 -169.0(4) . . . . ?
C1 C6 C13 C14 -115.4(5) . . . . ?
C5 C6 C13 C14 65.3(5) . . . . ?
C12 C13 C14 C15 -68.8(5) . . . . ?
C6 C13 C14 C15 61.6(5) . . . . ?
C12 C13 C14 C19 108.9(5) . . . . ?
C6 C13 C14 C19 -120.6(5) . . . . ?
C19 C14 C15 C16 0.4(6) . . . . ?
C13 C14 C15 C16 178.3(4) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 -1.0(7) . . . . ?
C17 C18 C19 C14 1.4(7) . . . . ?
C17 C18 C19 C20 -178.6(4) . . . . ?
C15 C14 C19 C18 -1.1(6) . . . . ?
C13 C14 C19 C18 -178.8(4) . . . . ?
C15 C14 C19 C20 179.0(4) . . . . ?
C13 C14 C19 C20 1.3(7) . . . . ?
O1 P1 C21 C26A 80.7(7) . . . . ?
C1 P1 C21 C26A -155.0(7) . . . . ?
C7 P1 C21 C26A -44.9(7) . . . . ?
O1 P1 C21 C22A -105.0(6) . . . . ?
C1 P1 C21 C22A 19.2(7) . . . . ?
C7 P1 C21 C22A 129.3(6) . . . . ?
C26A C21 C22A C23A -7.3(12) . . . . ?
P1 C21 C22A C23A 178.2(7) . . . . ?
C25A C24 C23A C22A 8.7(16) . . . . ?
C21 C22A C23A C24 -1.4(14) . . . . ?
C23A C24 C25A C26A -7.0(17) . . . . ?
C22A C21 C26A C25A 9.2(14) . . . . ?
P1 C21 C26A C25A -176.3(8) . . . . ?
C24 C25A C26A C21 -2.3(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.858
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.225
####################################################################### 
# 
# 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_trans6aaMe
_database_code_depnum_ccdc_archive 'CCDC 1553532'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3,7-dimethoxy-5-phenyl-10-(o-tolyl)-10H-acridophosphine 5-oxide
;
_chemical_name_common            trans6aaMe
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 O3 P'
_chemical_formula_sum            'C28 H25 O3 P'
_chemical_formula_weight         440.45

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'
O O 0.0106 0.0060 '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'

_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                   7.4318(16)
_cell_length_b                   19.171(4)
_cell_length_c                   15.802(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.986(3)
_cell_angle_gamma                90
_cell_volume                     2242.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5361
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Single Crystal X-ray diffractometer equipped with 
FR-X generator, Varimax optics, and PILATUS 200K photon 
counting detector
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29556
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.123
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5130
_reflns_number_gt                4550
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0388P)²+1.4590P] 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         5130
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_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
P1 P 0.50907(5) 0.21602(2) 0.09153(2) 0.01579(9) Uani 1 1 d . . . . .
O1 O 0.31332(14) 0.19915(6) 0.07469(6) 0.0224(2) Uani 1 1 d . . . . .
O2 O 0.65065(16) 0.36228(6) -0.16801(6) 0.0255(2) Uani 1 1 d . . . . .
O3 O 0.63584(17) 0.10858(6) 0.38205(7) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.58128(18) 0.22645(7) 0.20187(8) 0.0162(3) Uani 1 1 d . . . . .
C8 C 0.58167(18) 0.36114(7) 0.18920(8) 0.0153(3) Uani 1 1 d . . . . .
H25 H 0.6787 0.3931 0.2141 0.018 Uiso 1 1 calc R U . . .
C9 C 0.60211(18) 0.29288(7) 0.23860(8) 0.0160(3) Uani 1 1 d . . . . .
C1 C 0.6502(2) 0.15195(7) 0.04712(9) 0.0190(3) Uani 1 1 d . . . . .
C10 C 0.57555(18) 0.29654(7) 0.04601(8) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.3907(2) 0.46428(7) 0.23491(9) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.40040(18) 0.39622(7) 0.20288(8) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.59136(19) 0.29624(7) -0.04229(9) 0.0180(3) Uani 1 1 d . . . . .
H1 H 0.5745 0.2541 -0.0736 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6361(2) 0.29597(8) 0.32696(9) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.6518 0.3403 0.3533 0.024 Uiso 1 1 calc R U . . .
C15 C 0.60183(18) 0.35724(7) 0.09400(8) 0.0155(3) Uani 1 1 d . . . . .
C16 C 0.6477(2) 0.23653(8) 0.37777(9) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.6690 0.2406 0.4377 0.025 Uiso 1 1 calc R U . . .
C17 C 0.64192(19) 0.41864(7) 0.05061(9) 0.0187(3) Uani 1 1 d . . . . .
H4 H 0.6599 0.4609 0.0816 0.022 Uiso 1 1 calc R U . . .
C18 C 0.63139(19) 0.35734(8) -0.08327(9) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.8380(2) 0.15836(8) 0.05602(9) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.8935 0.1933 0.0920 0.027 Uiso 1 1 calc R U . . .
C27 C 0.6324(2) 0.29940(8) -0.21690(9) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.7187 0.2646 -0.1926 0.039 Uiso 1 1 calc R U . . .
H13 H 0.6569 0.3092 -0.2757 0.039 Uiso 1 1 calc R U . . .
H14 H 0.5093 0.2813 -0.2159 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6559(2) 0.41900(8) -0.03616(9) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.6822 0.4613 -0.0639 0.025 Uiso 1 1 calc R U . . .
C20 C 0.6275(2) 0.17083(8) 0.33969(9) 0.0204(3) Uani 1 1 d . . . . .
C21 C 0.59604(19) 0.16624(7) 0.25189(9) 0.0194(3) Uani 1 1 d . . . . .
H7 H 0.5844 0.1217 0.2256 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2194(2) 0.49360(8) 0.24009(10) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.2106 0.5398 0.2610 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0629(2) 0.45723(9) 0.21572(10) 0.0271(3) Uani 1 1 d . . . . .
H16 H -0.0515 0.4787 0.2190 0.033 Uiso 1 1 calc R U . . .
C24 C 0.24161(19) 0.35933(8) 0.18008(9) 0.0198(3) Uani 1 1 d . . . . .
H17 H 0.2491 0.3129 0.1598 0.024 Uiso 1 1 calc R U . . .
C28 C 0.6401(2) 0.11153(9) 0.47282(9) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.7540 0.1326 0.4960 0.041 Uiso 1 1 calc R U . . .
H19 H 0.6306 0.0642 0.4955 0.041 Uiso 1 1 calc R U . . .
H20 H 0.5387 0.1398 0.4891 0.041 Uiso 1 1 calc R U . . .
C25 C 0.5559(2) 0.50734(8) 0.26339(10) 0.0243(3) Uani 1 1 d . . . . .
H21 H 0.6164 0.5219 0.2136 0.036 Uiso 1 1 calc R U . . .
H22 H 0.6391 0.4793 0.3010 0.036 Uiso 1 1 calc R U . . .
H23 H 0.5190 0.5487 0.2940 0.036 Uiso 1 1 calc R U . . .
C3 C 0.8611(2) 0.06291(9) -0.04080(10) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.9331 0.0328 -0.0716 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5683(2) 0.10054(8) -0.00509(10) 0.0262(3) Uani 1 1 d . . . . .
H9 H 0.4405 0.0959 -0.0107 0.031 Uiso 1 1 calc R U . . .
C26 C 0.0732(2) 0.38902(8) 0.18640(10) 0.0248(3) Uani 1 1 d . . . . .
H24 H -0.0336 0.3632 0.1709 0.030 Uiso 1 1 calc R U . . .
C5 C 0.9438(2) 0.11358(8) 0.01222(10) 0.0274(3) Uani 1 1 d . . . . .
H10 H 1.0717 0.1175 0.0184 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6751(3) 0.05586(9) -0.04915(11) 0.0334(4) Uani 1 1 d . . . . .
H11 H 0.6202 0.0206 -0.0849 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.
;

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 O1 1.4915(11) . ?
P1 C7 1.7904(14) . ?
P1 C10 1.7906(14) . ?
P1 C1 1.7972(15) . ?
O2 C18 1.3624(17) . ?
O2 C27 1.4318(18) . ?
O3 C20 1.3669(17) . ?
O3 C28 1.4332(18) . ?
C7 C21 1.3979(19) . ?
C7 C9 1.4024(19) . ?
C8 C9 1.5245(19) . ?
C8 C15 1.5265(18) . ?
C8 C12 1.5377(18) . ?
C9 C14 1.3984(19) . ?
C1 C4 1.391(2) . ?
C1 C2 1.396(2) . ?
C10 C15 1.3934(19) . ?
C10 C13 1.4104(19) . ?
C11 C22 1.401(2) . ?
C11 C12 1.4036(19) . ?
C11 C25 1.515(2) . ?
C12 C24 1.396(2) . ?
C13 C18 1.3832(19) . ?
C14 C16 1.392(2) . ?
C15 C17 1.4072(19) . ?
C16 C20 1.398(2) . ?
C17 C19 1.384(2) . ?
C18 C19 1.400(2) . ?
C2 C5 1.389(2) . ?
C20 C21 1.390(2) . ?
C22 C23 1.382(2) . ?
C23 C26 1.392(2) . ?
C24 C26 1.386(2) . ?
C3 C6 1.383(3) . ?
C3 C5 1.391(2) . ?
C4 C6 1.395(2) . ?

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
O1 P1 C7 113.77(6) . . ?
O1 P1 C10 114.46(6) . . ?
C7 P1 C10 103.01(7) . . ?
O1 P1 C1 112.07(7) . . ?
C7 P1 C1 108.72(7) . . ?
C10 P1 C1 103.98(6) . . ?
C18 O2 C27 117.30(11) . . ?
C20 O3 C28 116.85(12) . . ?
C21 C7 C9 121.02(12) . . ?
C21 C7 P1 117.42(10) . . ?
C9 C7 P1 121.16(10) . . ?
C9 C8 C15 116.65(11) . . ?
C9 C8 C12 110.68(11) . . ?
C15 C8 C12 108.79(11) . . ?
C14 C9 C7 117.10(12) . . ?
C14 C9 C8 118.43(12) . . ?
C7 C9 C8 124.41(12) . . ?
C4 C1 C2 120.30(14) . . ?
C4 C1 P1 118.38(12) . . ?
C2 C1 P1 120.86(11) . . ?
C15 C10 C13 121.48(12) . . ?
C15 C10 P1 122.13(10) . . ?
C13 C10 P1 116.32(10) . . ?
C22 C11 C12 118.00(14) . . ?
C22 C11 C25 118.75(13) . . ?
C12 C11 C25 123.25(13) . . ?
C24 C12 C11 119.70(13) . . ?
C24 C12 C8 118.25(12) . . ?
C11 C12 C8 122.02(12) . . ?
C18 C13 C10 119.96(13) . . ?
C16 C14 C9 122.53(13) . . ?
C10 C15 C17 117.32(12) . . ?
C10 C15 C8 123.78(12) . . ?
C17 C15 C8 118.84(12) . . ?
C14 C16 C20 119.36(13) . . ?
C19 C17 C15 121.61(13) . . ?
O2 C18 C13 124.35(13) . . ?
O2 C18 C19 116.35(12) . . ?
C13 C18 C19 119.29(13) . . ?
C5 C2 C1 119.98(14) . . ?
C17 C19 C18 120.33(13) . . ?
O3 C20 C21 115.47(13) . . ?
O3 C20 C16 125.25(13) . . ?
C21 C20 C16 119.28(13) . . ?
C20 C21 C7 120.69(13) . . ?
C23 C22 C11 121.92(14) . . ?
C22 C23 C26 119.80(14) . . ?
C26 C24 C12 121.43(14) . . ?
C6 C3 C5 120.75(15) . . ?
C1 C4 C6 119.48(16) . . ?
C24 C26 C23 119.10(14) . . ?
C2 C5 C3 119.50(16) . . ?
C3 C6 C4 119.99(15) . . ?

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
O1 P1 C7 C21 73.08(12) . . . . ?
C10 P1 C7 C21 -162.43(11) . . . . ?
C1 P1 C7 C21 -52.55(13) . . . . ?
O1 P1 C7 C9 -99.78(12) . . . . ?
C10 P1 C7 C9 24.71(13) . . . . ?
C1 P1 C7 C9 134.59(11) . . . . ?
C21 C7 C9 C14 -0.7(2) . . . . ?
P1 C7 C9 C14 171.92(10) . . . . ?
C21 C7 C9 C8 -177.76(13) . . . . ?
P1 C7 C9 C8 -5.15(19) . . . . ?
C15 C8 C9 C14 162.08(12) . . . . ?
C12 C8 C9 C14 -72.84(16) . . . . ?
C15 C8 C9 C7 -20.88(19) . . . . ?
C12 C8 C9 C7 104.19(15) . . . . ?
O1 P1 C1 C4 7.76(14) . . . . ?
C7 P1 C1 C4 134.38(12) . . . . ?
C10 P1 C1 C4 -116.39(12) . . . . ?
O1 P1 C1 C2 179.99(11) . . . . ?
C7 P1 C1 C2 -53.38(13) . . . . ?
C10 P1 C1 C2 55.84(13) . . . . ?
O1 P1 C10 C15 100.94(12) . . . . ?
C7 P1 C10 C15 -23.09(13) . . . . ?
C1 P1 C10 C15 -136.47(12) . . . . ?
O1 P1 C10 C13 -76.01(12) . . . . ?
C7 P1 C10 C13 159.96(11) . . . . ?
C1 P1 C10 C13 46.57(12) . . . . ?
C22 C11 C12 C24 -2.1(2) . . . . ?
C25 C11 C12 C24 178.31(13) . . . . ?
C22 C11 C12 C8 175.96(12) . . . . ?
C25 C11 C12 C8 -3.6(2) . . . . ?
C9 C8 C12 C24 -58.92(16) . . . . ?
C15 C8 C12 C24 70.49(15) . . . . ?
C9 C8 C12 C11 123.00(13) . . . . ?
C15 C8 C12 C11 -107.58(14) . . . . ?
C15 C10 C13 C18 -0.9(2) . . . . ?
P1 C10 C13 C18 176.09(11) . . . . ?
C7 C9 C14 C16 -0.6(2) . . . . ?
C8 C9 C14 C16 176.67(13) . . . . ?
C13 C10 C15 C17 1.0(2) . . . . ?
P1 C10 C15 C17 -175.77(10) . . . . ?
C13 C10 C15 C8 178.33(13) . . . . ?
P1 C10 C15 C8 1.53(19) . . . . ?
C9 C8 C15 C10 22.83(19) . . . . ?
C12 C8 C15 C10 -103.19(15) . . . . ?
C9 C8 C15 C17 -159.91(12) . . . . ?
C12 C8 C15 C17 74.07(15) . . . . ?
C9 C14 C16 C20 1.0(2) . . . . ?
C10 C15 C17 C19 -0.4(2) . . . . ?
C8 C15 C17 C19 -177.79(13) . . . . ?
C27 O2 C18 C13 -1.6(2) . . . . ?
C27 O2 C18 C19 177.88(13) . . . . ?
C10 C13 C18 O2 179.53(13) . . . . ?
C10 C13 C18 C19 0.0(2) . . . . ?
C4 C1 C2 C5 0.4(2) . . . . ?
P1 C1 C2 C5 -171.68(11) . . . . ?
C15 C17 C19 C18 -0.5(2) . . . . ?
O2 C18 C19 C17 -178.90(13) . . . . ?
C13 C18 C19 C17 0.6(2) . . . . ?
C28 O3 C20 C21 -170.64(13) . . . . ?
C28 O3 C20 C16 9.2(2) . . . . ?
C14 C16 C20 O3 -179.99(14) . . . . ?
C14 C16 C20 C21 -0.1(2) . . . . ?
O3 C20 C21 C7 178.75(13) . . . . ?
C16 C20 C21 C7 -1.1(2) . . . . ?
C9 C7 C21 C20 1.6(2) . . . . ?
P1 C7 C21 C20 -171.32(11) . . . . ?
C12 C11 C22 C23 0.8(2) . . . . ?
C25 C11 C22 C23 -179.61(14) . . . . ?
C11 C22 C23 C26 1.1(2) . . . . ?
C11 C12 C24 C26 1.6(2) . . . . ?
C8 C12 C24 C26 -176.55(13) . . . . ?
C2 C1 C4 C6 -0.6(2) . . . . ?
P1 C1 C4 C6 171.66(13) . . . . ?
C12 C24 C26 C23 0.3(2) . . . . ?
C22 C23 C26 C24 -1.7(2) . . . . ?
C1 C2 C5 C3 0.5(2) . . . . ?
C6 C3 C5 C2 -1.2(2) . . . . ?
C5 C3 C6 C4 1.0(3) . . . . ?
C1 C4 C6 C3 -0.1(3) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

