# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_201608113
_database_code_depnum_ccdc_archive 'CCDC 1527635'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2016-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N2 O2 P'
_chemical_formula_sum            'C28 H21 N2 O2 P'
_chemical_formula_weight         448.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C43H53O14N4P1
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.9056(3)
_cell_length_b                   8.9810(2)
_cell_length_c                   20.4045(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.848(3)
_cell_angle_gamma                90
_cell_volume                     2263.47(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3605
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7770
_cell_measurement_theta_min      4.5250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8616
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.578
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   66.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega   74.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega   -3.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   25.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega  -23.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega   47.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   50.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 16 omega  111.00  140.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   88.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00  107.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 19 omega   51.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 20 omega  103.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0069513000
_diffrn_orient_matrix_UB_12      -0.0677625000
_diffrn_orient_matrix_UB_13      0.0704859000
_diffrn_orient_matrix_UB_21      -0.0320046000
_diffrn_orient_matrix_UB_22      0.1512605000
_diffrn_orient_matrix_UB_23      0.0239902000
_diffrn_orient_matrix_UB_31      -0.1204075000
_diffrn_orient_matrix_UB_32      -0.0442257000
_diffrn_orient_matrix_UB_33      -0.0259808000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3395
_reflns_number_total             4050
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00060(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.4706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1138
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.79527(14) 1.0392(2) 0.36759(9) 0.0391(4) Uani 1 1 d . . . . .
C2 C 0.74864(16) 1.1718(2) 0.33947(11) 0.0481(5) Uani 1 1 d . . . . .
H2 H 0.7155 1.1782 0.2926 0.058 Uiso 1 1 calc R . . . .
C3 C 0.75094(19) 1.2947(3) 0.38042(13) 0.0607(6) Uani 1 1 d . . . . .
H3 H 0.7187 1.3832 0.3612 0.073 Uiso 1 1 calc R . . . .
C4 C 0.8006(2) 1.2865(3) 0.44923(13) 0.0647(6) Uani 1 1 d . . . . .
H4 H 0.8024 1.3695 0.4768 0.078 Uiso 1 1 calc R . . . .
C5 C 0.8479(2) 1.1554(3) 0.47769(12) 0.0688(7) Uani 1 1 d . . . . .
H5 H 0.8818 1.1506 0.5245 0.083 Uiso 1 1 calc R . . . .
C6 C 0.84570(18) 1.0301(3) 0.43743(11) 0.0561(5) Uani 1 1 d . . . . .
H6 H 0.8775 0.9416 0.4570 0.067 Uiso 1 1 calc R . . . .
C7 C 0.67288(14) 0.7701(2) 0.31851(9) 0.0387(4) Uani 1 1 d . . . . .
C8 C 0.63500(17) 0.7681(3) 0.37536(11) 0.0522(5) Uani 1 1 d . . . . .
H8 H 0.6705 0.8221 0.4143 0.063 Uiso 1 1 calc R . . . .
C9 C 0.54384(19) 0.6852(3) 0.37411(12) 0.0645(6) Uani 1 1 d . . . . .
H9 H 0.5178 0.6849 0.4121 0.077 Uiso 1 1 calc R . . . .
C10 C 0.49180(18) 0.6037(3) 0.31747(13) 0.0675(7) Uani 1 1 d . . . . .
H10 H 0.4303 0.5492 0.3169 0.081 Uiso 1 1 calc R . . . .
C11 C 0.53068(19) 0.6024(3) 0.26135(12) 0.0675(7) Uani 1 1 d . . . . .
H11 H 0.4967 0.5448 0.2233 0.081 Uiso 1 1 calc R . . . .
C12 C 0.61994(16) 0.6867(3) 0.26167(11) 0.0532(5) Uani 1 1 d . . . . .
H12 H 0.6449 0.6876 0.2233 0.064 Uiso 1 1 calc R . . . .
C13 C 0.90602(14) 0.7710(2) 0.34394(8) 0.0370(4) Uani 1 1 d . . . . .
C14 C 0.90535(15) 0.6426(2) 0.37971(9) 0.0412(4) Uani 1 1 d . . . . .
H14 H 0.8436 0.6193 0.3924 0.049 Uiso 1 1 calc R . . . .
C15 C 0.99365(15) 0.5443(2) 0.39824(10) 0.0431(4) Uani 1 1 d . . . . .
H15 H 0.9903 0.4589 0.4233 0.052 Uiso 1 1 calc R . . . .
C16 C 1.08528(14) 0.5754(2) 0.37899(9) 0.0388(4) Uani 1 1 d . . . . .
C17 C 1.09225(14) 0.7132(2) 0.34542(9) 0.0369(4) Uani 1 1 d . . . . .
C18 C 1.00340(14) 0.8120(2) 0.32786(8) 0.0367(4) Uani 1 1 d . . . . .
C19 C 1.01777(16) 0.9484(2) 0.29734(10) 0.0469(5) Uani 1 1 d . . . . .
H19 H 0.9618 1.0176 0.2855 0.056 Uiso 1 1 calc R . . . .
C20 C 1.11448(17) 0.9780(3) 0.28531(11) 0.0543(5) Uani 1 1 d . . . . .
H20 H 1.1255 1.0679 0.2656 0.065 Uiso 1 1 calc R . . . .
C21 C 1.19667(17) 0.8712(3) 0.30305(11) 0.0517(5) Uani 1 1 d . . . . .
H21 H 1.2613 0.8920 0.2934 0.062 Uiso 1 1 calc R . . . .
C22 C 1.19809(16) 0.3574(2) 0.42854(10) 0.0470(5) Uani 1 1 d . . . . .
C23 C 1.30263(16) 0.2849(2) 0.42865(9) 0.0468(5) Uani 1 1 d . . . . .
C24 C 1.3093(2) 0.1316(3) 0.42923(12) 0.0595(6) Uani 1 1 d . . . . .
H24 H 1.2497 0.0746 0.4305 0.071 Uiso 1 1 calc R . . . .
C25 C 1.4047(2) 0.0622(3) 0.42789(12) 0.0734(8) Uani 1 1 d . . . . .
H25 H 1.4082 -0.0412 0.4267 0.088 Uiso 1 1 calc R . . . .
C26 C 1.4939(2) 0.1458(4) 0.42830(14) 0.0774(8) Uani 1 1 d . . . . .
H26 H 1.5579 0.0991 0.4277 0.093 Uiso 1 1 calc R . . . .
C27 C 1.4887(2) 0.2976(4) 0.42966(14) 0.0752(8) Uani 1 1 d . . . . .
H27 H 1.5498 0.3540 0.4311 0.090 Uiso 1 1 calc R . . . .
C28 C 1.39304(18) 0.3678(3) 0.42885(12) 0.0594(6) Uani 1 1 d . . . . .
H28 H 1.3894 0.4712 0.4284 0.071 Uiso 1 1 calc R . . . .
N1 N 1.18864(13) 0.74334(19) 0.33243(8) 0.0448(4) Uani 1 1 d . . . . .
N2 N 1.17477(14) 0.4820(2) 0.39001(9) 0.0462(4) Uani 1 1 d . . . . .
H2A H 1.2118(19) 0.498(3) 0.3627(13) 0.064(7) Uiso 1 1 d . . . . .
O1 O 0.76791(11) 0.92796(17) 0.23860(6) 0.0476(3) Uani 1 1 d . . . . .
O2 O 1.14148(15) 0.3074(2) 0.46191(10) 0.0790(6) Uani 1 1 d . . . . .
P1 P 0.78517(3) 0.88214(5) 0.31095(2) 0.03592(15) 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 C2 1.382(3) . ?
C1 C6 1.387(3) . ?
C1 P1 1.8042(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(3) . ?
C7 C12 1.383(3) . ?
C7 P1 1.8070(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 C18 1.436(2) . ?
C13 P1 1.8092(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.404(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 C17 1.430(3) . ?
C16 N2 1.392(2) . ?
C17 C18 1.412(3) . ?
C17 N1 1.372(2) . ?
C18 C19 1.410(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(3) . ?
C21 H21 0.9300 . ?
C21 N1 1.313(3) . ?
C22 C23 1.498(3) . ?
C22 N2 1.351(3) . ?
C22 O2 1.220(3) . ?
C23 C24 1.379(3) . ?
C23 C28 1.383(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9300 . ?
N2 H2A 0.84(2) . ?
O1 P1 1.4858(13) . ?

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
C2 C1 C6 119.70(19) . . ?
C2 C1 P1 117.77(14) . . ?
C6 C1 P1 122.52(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 P1 124.48(15) . . ?
C12 C7 C8 119.14(18) . . ?
C12 C7 P1 116.32(15) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C18 118.71(16) . . ?
C14 C13 P1 121.75(14) . . ?
C18 C13 P1 119.38(14) . . ?
C13 C14 H14 118.5 . . ?
C13 C14 C15 122.98(17) . . ?
C15 C14 H14 118.5 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.50(18) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 119.34(17) . . ?
C15 C16 N2 124.90(18) . . ?
N2 C16 C17 115.76(16) . . ?
C18 C17 C16 120.44(16) . . ?
N1 C17 C16 116.73(16) . . ?
N1 C17 C18 122.83(17) . . ?
C17 C18 C13 118.74(16) . . ?
C19 C18 C13 124.03(17) . . ?
C19 C18 C17 117.19(17) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.50(19) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 118.9(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 117.8 . . ?
N1 C21 C20 124.34(18) . . ?
N1 C21 H21 117.8 . . ?
N2 C22 C23 114.20(17) . . ?
O2 C22 C23 121.62(19) . . ?
O2 C22 N2 124.16(19) . . ?
C24 C23 C22 119.2(2) . . ?
C24 C23 C28 119.1(2) . . ?
C28 C23 C22 121.7(2) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.3(2) . . ?
C27 C28 H28 119.8 . . ?
C21 N1 C17 117.18(17) . . ?
C16 N2 H2A 113.2(18) . . ?
C22 N2 C16 128.90(17) . . ?
C22 N2 H2A 116.7(18) . . ?
C1 P1 C7 106.94(8) . . ?
C1 P1 C13 107.37(8) . . ?
C7 P1 C13 106.70(9) . . ?
O1 P1 C1 112.46(9) . . ?
O1 P1 C7 110.24(8) . . ?
O1 P1 C13 112.79(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.84(2) 2.25(3) 2.966(2) 143(2) 2_745

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
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 P1 C7 -97.88(16) . . . . ?
C2 C1 P1 C13 147.92(15) . . . . ?
C2 C1 P1 O1 23.28(18) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C1 P1 C7 80.87(18) . . . . ?
C6 C1 P1 C13 -33.3(2) . . . . ?
C6 C1 P1 O1 -157.98(17) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C7 P1 C1 -25.1(2) . . . . ?
C8 C7 P1 C13 89.57(19) . . . . ?
C8 C7 P1 O1 -147.63(17) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -1.9(4) . . . . ?
C10 C11 C12 C7 1.6(4) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C12 C7 P1 C1 152.08(16) . . . . ?
C12 C7 P1 C13 -93.26(17) . . . . ?
C12 C7 P1 O1 29.54(19) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C13 C18 C19 C20 178.73(18) . . . . ?
C14 C13 C18 C17 4.3(2) . . . . ?
C14 C13 C18 C19 -173.45(18) . . . . ?
C14 C13 P1 C1 102.17(16) . . . . ?
C14 C13 P1 C7 -12.19(18) . . . . ?
C14 C13 P1 O1 -133.38(15) . . . . ?
C14 C15 C16 C17 5.1(3) . . . . ?
C14 C15 C16 N2 -175.28(18) . . . . ?
C15 C16 C17 C18 -4.4(3) . . . . ?
C15 C16 C17 N1 174.91(17) . . . . ?
C15 C16 N2 C22 -10.3(3) . . . . ?
C16 C17 C18 C13 -0.4(2) . . . . ?
C16 C17 C18 C19 177.53(16) . . . . ?
C16 C17 N1 C21 -178.46(17) . . . . ?
C17 C16 N2 C22 169.35(19) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C13 C14 C15 -3.7(3) . . . . ?
C18 C13 P1 C1 -82.66(15) . . . . ?
C18 C13 P1 C7 162.97(14) . . . . ?
C18 C13 P1 O1 41.79(17) . . . . ?
C18 C17 N1 C21 0.8(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C19 C20 C21 N1 -1.7(3) . . . . ?
C20 C21 N1 C17 0.9(3) . . . . ?
C22 C23 C24 C25 178.64(19) . . . . ?
C22 C23 C28 C27 179.3(2) . . . . ?
C23 C22 N2 C16 -179.86(19) . . . . ?
C23 C24 C25 C26 2.2(4) . . . . ?
C24 C23 C28 C27 0.0(3) . . . . ?
C24 C25 C26 C27 -0.4(4) . . . . ?
C25 C26 C27 C28 -1.7(4) . . . . ?
C26 C27 C28 C23 1.9(4) . . . . ?
C28 C23 C24 C25 -2.0(3) . . . . ?
N1 C17 C18 C13 -179.62(16) . . . . ?
N1 C17 C18 C19 -1.7(3) . . . . ?
N2 C16 C17 C18 176.01(16) . . . . ?
N2 C16 C17 N1 -4.7(2) . . . . ?
N2 C22 C23 C24 -142.9(2) . . . . ?
N2 C22 C23 C28 37.7(3) . . . . ?
O2 C22 C23 C24 38.4(3) . . . . ?
O2 C22 C23 C28 -140.9(2) . . . . ?
O2 C22 N2 C16 -1.2(4) . . . . ?
P1 C1 C2 C3 178.13(16) . . . . ?
P1 C1 C6 C5 -178.58(18) . . . . ?
P1 C7 C8 C9 175.89(18) . . . . ?
P1 C7 C12 C11 -177.36(19) . . . . ?
P1 C13 C14 C15 171.52(15) . . . . ?
P1 C13 C18 C17 -170.98(13) . . . . ?
P1 C13 C18 C19 11.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201608114
_database_code_depnum_ccdc_archive 'CCDC 1527636'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2016-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N2 O2 P'
_chemical_formula_sum            'C28 H21 N2 O2 P'
_chemical_formula_weight         448.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C43H53O14N4P1
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.3374(5)
_cell_length_b                   9.7100(4)
_cell_length_c                   18.7718(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.341(4)
_cell_angle_gamma                90
_cell_volume                     2520.23(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3623
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2830
_cell_measurement_theta_min      4.4950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.471
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega   17.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -27.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   12.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  9 omega  -31.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   59.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega   98.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 17 omega  129.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   92.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 19 omega   51.00  114.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1048568000
_diffrn_orient_matrix_UB_12      -0.0404852000
_diffrn_orient_matrix_UB_13      -0.0395893000
_diffrn_orient_matrix_UB_21      -0.0253601000
_diffrn_orient_matrix_UB_22      -0.0027044000
_diffrn_orient_matrix_UB_23      0.0748083000
_diffrn_orient_matrix_UB_31      -0.0281554000
_diffrn_orient_matrix_UB_32      0.1532109000
_diffrn_orient_matrix_UB_33      -0.0092165000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3587
_reflns_number_total             4509
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00086(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+0.1236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1436
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C20(H20), C21(H21), C24(H24), C25(H25),
  C26(H26), C27(H27), C28(H28), N2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.30849(14) 0.5745(2) 0.48122(12) 0.0613(5) Uani 1 1 d . . . . .
C2 C 0.26370(19) 0.5770(3) 0.53787(14) 0.0806(7) Uani 1 1 d . . . . .
H2 H 0.2038 0.5350 0.5317 0.097 Uiso 1 1 calc R . . . .
C3 C 0.3075(2) 0.6416(3) 0.60371(16) 0.0981(9) Uani 1 1 d . . . . .
H3 H 0.2770 0.6429 0.6417 0.118 Uiso 1 1 calc R . . . .
C4 C 0.3959(2) 0.7040(3) 0.61353(17) 0.0946(8) Uani 1 1 d . . . . .
H4 H 0.4250 0.7482 0.6578 0.114 Uiso 1 1 calc R . . . .
C5 C 0.4408(2) 0.7007(3) 0.55802(18) 0.0946(8) Uani 1 1 d . . . . .
H5 H 0.5009 0.7422 0.5647 0.114 Uiso 1 1 calc R . . . .
C6 C 0.39757(16) 0.6360(3) 0.49180(14) 0.0766(6) Uani 1 1 d . . . . .
H6 H 0.4289 0.6341 0.4543 0.092 Uiso 1 1 calc R . . . .
C7 C 0.28361(13) 0.3077(2) 0.40833(10) 0.0606(5) Uani 1 1 d . . . . .
C8 C 0.32177(18) 0.2493(3) 0.47723(12) 0.0765(6) Uani 1 1 d . . . . .
H8 H 0.3306 0.3028 0.5196 0.092 Uiso 1 1 calc R . . . .
C9 C 0.3467(2) 0.1120(3) 0.48306(15) 0.0924(8) Uani 1 1 d . . . . .
H9 H 0.3728 0.0733 0.5294 0.111 Uiso 1 1 calc R . . . .
C10 C 0.3332(2) 0.0315(3) 0.42067(16) 0.0863(7) Uani 1 1 d . . . . .
H10 H 0.3501 -0.0612 0.4249 0.104 Uiso 1 1 calc R . . . .
C11 C 0.29484(17) 0.0883(3) 0.35258(14) 0.0790(7) Uani 1 1 d . . . . .
H11 H 0.2851 0.0338 0.3105 0.095 Uiso 1 1 calc R . . . .
C12 C 0.27078(14) 0.2245(3) 0.34616(11) 0.0705(6) Uani 1 1 d . . . . .
H12 H 0.2454 0.2623 0.2995 0.085 Uiso 1 1 calc R . . . .
C13 C 0.12228(14) 0.7468(3) 0.33399(14) 0.0736(6) Uani 1 1 d . . . . .
H13 H 0.1875 0.7436 0.3352 0.088 Uiso 1 1 calc R . . . .
C14 C 0.07014(16) 0.8625(3) 0.31043(16) 0.0839(7) Uani 1 1 d . . . . .
H14 H 0.1008 0.9381 0.2963 0.101 Uiso 1 1 calc R . . . .
C15 C -0.02899(15) 0.8714(2) 0.30675(14) 0.0748(6) Uani 1 1 d . . . . .
H15 H -0.0629 0.9521 0.2906 0.090 Uiso 1 1 calc R . . . .
C16 C -0.07518(13) 0.7606(2) 0.32704(11) 0.0593(5) Uani 1 1 d . . . . .
C17 C -0.02216(13) 0.6387(2) 0.35355(10) 0.0567(4) Uani 1 1 d . . . . .
C18 C 0.07762(13) 0.6315(2) 0.35670(10) 0.0574(4) Uani 1 1 d . . . . .
C19 C 0.12614(14) 0.5046(2) 0.38257(11) 0.0595(5) Uani 1 1 d . . . . .
C20 C 0.07460(16) 0.4014(3) 0.40193(15) 0.0765(6) Uani 1 1 d . . . . .
H20 H 0.1043 0.3177 0.4181 0.092 Uiso 1 1 calc R . . . .
C21 C -0.02426(16) 0.4207(3) 0.39766(17) 0.0817(7) Uani 1 1 d . . . . .
H21 H -0.0576 0.3481 0.4119 0.098 Uiso 1 1 calc R . . . .
C22 C -0.24120(14) 0.8561(2) 0.30147(11) 0.0613(5) Uani 1 1 d . . . . .
C23 C -0.34168(13) 0.8228(2) 0.30621(10) 0.0558(4) Uani 1 1 d . . . . .
C24 C -0.40388(17) 0.9332(2) 0.30301(13) 0.0708(6) Uani 1 1 d . . . . .
H24 H -0.3822 1.0220 0.2979 0.085 Uiso 1 1 calc R . . . .
C25 C -0.49713(17) 0.9136(3) 0.30731(15) 0.0817(7) Uani 1 1 d . . . . .
H25 H -0.5381 0.9886 0.3052 0.098 Uiso 1 1 calc R . . . .
C26 C -0.52974(15) 0.7820(3) 0.31475(12) 0.0723(6) Uani 1 1 d . . . . .
H26 H -0.5929 0.7681 0.3174 0.087 Uiso 1 1 calc R . . . .
C27 C -0.46901(16) 0.6719(3) 0.31823(13) 0.0721(6) Uani 1 1 d . . . . .
H27 H -0.4908 0.5832 0.3235 0.087 Uiso 1 1 calc R . . . .
C28 C -0.37502(15) 0.6927(2) 0.31391(13) 0.0653(5) Uani 1 1 d . . . . .
H28 H -0.3341 0.6176 0.3163 0.078 Uiso 1 1 calc R . . . .
N1 N -0.07162(12) 0.53358(19) 0.37501(11) 0.0690(5) Uani 1 1 d . . . . .
N2 N -0.17432(11) 0.75629(18) 0.32361(10) 0.0641(4) Uani 1 1 d . . . . .
H2A H -0.1950 0.6803 0.3374 0.077 Uiso 1 1 calc R . . . .
O1 O 0.29017(11) 0.5445(2) 0.33211(9) 0.0787(5) Uani 1 1 d . . . . .
O2 O -0.22271(13) 0.96807(18) 0.27991(12) 0.0915(6) Uani 1 1 d . . . . .
P1 P 0.25624(3) 0.48864(6) 0.39426(3) 0.06035(19) 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 C2 1.380(3) . ?
C1 C6 1.376(3) . ?
C1 P1 1.810(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(3) . ?
C7 C12 1.391(3) . ?
C7 P1 1.804(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.357(3) . ?
C13 C18 1.411(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.407(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(3) . ?
C16 C17 1.424(3) . ?
C16 N2 1.406(2) . ?
C17 C18 1.418(3) . ?
C17 N1 1.363(3) . ?
C18 C19 1.435(3) . ?
C19 C20 1.351(3) . ?
C19 P1 1.8262(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.411(3) . ?
C21 H21 0.9300 . ?
C21 N1 1.300(3) . ?
C22 C23 1.502(3) . ?
C22 N2 1.350(2) . ?
C22 O2 1.213(3) . ?
C23 C24 1.385(3) . ?
C23 C28 1.372(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.369(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.386(3) . ?
C28 H28 0.9300 . ?
N2 H2A 0.8600 . ?
O1 P1 1.4806(16) . ?

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
C2 C1 P1 122.49(17) . . ?
C6 C1 C2 119.0(2) . . ?
C6 C1 P1 118.50(17) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.3(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C12 118.5(2) . . ?
C8 C7 P1 123.52(17) . . ?
C12 C7 P1 117.86(16) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C18 120.03(19) . . ?
C18 C13 H13 120.0 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 121.9(2) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 119.85(18) . . ?
C15 C16 N2 124.64(19) . . ?
N2 C16 C17 115.50(17) . . ?
C18 C17 C16 119.65(17) . . ?
N1 C17 C16 117.04(17) . . ?
N1 C17 C18 123.31(18) . . ?
C13 C18 C17 118.84(18) . . ?
C13 C18 C19 124.44(18) . . ?
C17 C18 C19 116.71(17) . . ?
C18 C19 P1 120.14(14) . . ?
C20 C19 C18 118.52(18) . . ?
C20 C19 P1 121.23(16) . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.9(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 118.0 . . ?
N1 C21 C20 124.1(2) . . ?
N1 C21 H21 118.0 . . ?
N2 C22 C23 116.20(18) . . ?
O2 C22 C23 120.69(18) . . ?
O2 C22 N2 123.10(19) . . ?
C24 C23 C22 116.57(19) . . ?
C28 C23 C22 124.82(18) . . ?
C28 C23 C24 118.61(19) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.7(2) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 119.9(2) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 C27 120.8(2) . . ?
C23 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C21 N1 C17 117.42(18) . . ?
C16 N2 H2A 115.9 . . ?
C22 N2 C16 128.29(18) . . ?
C22 N2 H2A 115.9 . . ?
C1 P1 C19 103.60(9) . . ?
C7 P1 C1 107.14(9) . . ?
C7 P1 C19 106.03(9) . . ?
O1 P1 C1 113.46(10) . . ?
O1 P1 C7 111.58(10) . . ?
O1 P1 C19 114.34(9) . . ?

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
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 P1 C7 -81.0(2) . . . . ?
C2 C1 P1 C19 30.9(2) . . . . ?
C2 C1 P1 O1 155.42(19) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C1 P1 C7 97.05(19) . . . . ?
C6 C1 P1 C19 -151.11(18) . . . . ?
C6 C1 P1 O1 -26.6(2) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C7 P1 C1 10.6(2) . . . . ?
C8 C7 P1 C19 -99.6(2) . . . . ?
C8 C7 P1 O1 135.35(19) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
C12 C7 C8 C9 0.4(4) . . . . ?
C12 C7 P1 C1 -165.55(16) . . . . ?
C12 C7 P1 C19 84.29(17) . . . . ?
C12 C7 P1 O1 -40.80(19) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C13 C18 C19 C20 -179.3(2) . . . . ?
C13 C18 C19 P1 4.5(3) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
C14 C13 C18 C19 -179.9(2) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C14 C15 C16 N2 -178.1(2) . . . . ?
C15 C16 C17 C18 -1.8(3) . . . . ?
C15 C16 C17 N1 178.0(2) . . . . ?
C15 C16 N2 C22 -0.8(4) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C16 C17 C18 C19 -178.79(18) . . . . ?
C16 C17 N1 C21 178.4(2) . . . . ?
C17 C16 N2 C22 179.5(2) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C17 C18 C19 P1 -176.12(15) . . . . ?
C18 C13 C14 C15 -0.9(4) . . . . ?
C18 C17 N1 C21 -1.7(3) . . . . ?
C18 C19 C20 C21 -1.1(4) . . . . ?
C18 C19 P1 C1 78.98(18) . . . . ?
C18 C19 P1 C7 -168.38(16) . . . . ?
C18 C19 P1 O1 -45.0(2) . . . . ?
C19 C20 C21 N1 0.8(5) . . . . ?
C20 C19 P1 C1 -97.1(2) . . . . ?
C20 C19 P1 C7 15.5(2) . . . . ?
C20 C19 P1 O1 138.9(2) . . . . ?
C20 C21 N1 C17 0.6(4) . . . . ?
C22 C23 C24 C25 -179.6(2) . . . . ?
C22 C23 C28 C27 179.6(2) . . . . ?
C23 C22 N2 C16 -178.06(19) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
C24 C23 C28 C27 0.2(3) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 0.1(3) . . . . ?
C28 C23 C24 C25 -0.1(3) . . . . ?
N1 C17 C18 C13 -179.2(2) . . . . ?
N1 C17 C18 C19 1.4(3) . . . . ?
N2 C16 C17 C18 177.93(18) . . . . ?
N2 C16 C17 N1 -2.2(3) . . . . ?
N2 C22 C23 C24 163.25(19) . . . . ?
N2 C22 C23 C28 -16.2(3) . . . . ?
O2 C22 C23 C24 -15.6(3) . . . . ?
O2 C22 C23 C28 164.9(2) . . . . ?
O2 C22 N2 C16 0.8(4) . . . . ?
P1 C1 C2 C3 178.7(2) . . . . ?
P1 C1 C6 C5 -178.8(2) . . . . ?
P1 C7 C8 C9 -175.7(2) . . . . ?
P1 C7 C12 C11 176.55(17) . . . . ?
P1 C19 C20 C21 175.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 149 50 ' '
2 0.500 0.500 0.000 149 50 ' '

####################################################################### 
# 
# 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_20170698
_database_code_depnum_ccdc_archive 'CCDC 1554232'
_audit_update_record             
;
2017-06-05 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H23 N2 O3 P'
_chemical_formula_sum            'C29 H23 N2 O3 P'
_chemical_formula_weight         478.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H70N2O2P1
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5853(9)
_cell_length_b                   9.8739(8)
_cell_length_c                   14.7007(14)
_cell_angle_alpha                103.110(8)
_cell_angle_beta                 94.035(8)
_cell_angle_gamma                114.371(8)
_cell_volume                     1213.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3074
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9490
_cell_measurement_theta_min      5.1250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8680
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.003
_diffrn_reflns_theta_max         67.003
_diffrn_reflns_theta_min         5.125
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -108.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega -104.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -37.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   -4.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega   61.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   -3.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega   57.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega   54.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega   28.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -124.0000   58.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 18 omega   37.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 19 omega   45.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 20 omega   37.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 21 omega   99.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 22 omega   53.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   73.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 30

#__ type_ start__ end____ width___ exp.time_
 24 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  128.00  153.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   39.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 27 omega   94.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
 28 omega   64.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
 29 omega   40.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -148.0000 -105.0000 94

#__ type_ start__ end____ width___ exp.time_
 30 omega  102.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1136452000
_diffrn_orient_matrix_UB_12      0.1717131000
_diffrn_orient_matrix_UB_13      0.0157059000
_diffrn_orient_matrix_UB_21      -0.0307724000
_diffrn_orient_matrix_UB_22      -0.0217059000
_diffrn_orient_matrix_UB_23      -0.1078005000
_diffrn_orient_matrix_UB_31      -0.1356213000
_diffrn_orient_matrix_UB_32      0.0444640000
_diffrn_orient_matrix_UB_33      0.0108153000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3472
_reflns_number_total             4325
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.1579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2116(2) 0.6984(3) 0.89656(15) 0.0601(5) Uani 1 1 d . . . . .
C2 C 0.1021(3) 0.7084(3) 0.95211(17) 0.0698(6) Uani 1 1 d . . . . .
H2 H 0.0313 0.6201 0.9652 0.084 Uiso 1 1 calc R . . . .
C3 C 0.0981(3) 0.8476(4) 0.98756(19) 0.0840(8) Uani 1 1 d . . . . .
H3 H 0.0249 0.8532 1.0247 0.101 Uiso 1 1 calc R . . . .
C4 C 0.2019(3) 0.9788(4) 0.9683(2) 0.0946(10) Uani 1 1 d . . . . .
H4 H 0.1988 1.0729 0.9923 0.114 Uiso 1 1 calc R . . . .
C5 C 0.3102(4) 0.9707(3) 0.9138(3) 0.1011(10) Uani 1 1 d . . . . .
H5 H 0.3803 1.0595 0.9007 0.121 Uiso 1 1 calc R . . . .
C6 C 0.3155(3) 0.8309(3) 0.8781(2) 0.0845(8) Uani 1 1 d . . . . .
H6 H 0.3895 0.8263 0.8414 0.101 Uiso 1 1 calc R . . . .
C7 C 0.4035(2) 0.5531(2) 0.82471(15) 0.0550(5) Uani 1 1 d . . . . .
C8 C 0.4285(3) 0.5516(3) 0.73333(17) 0.0671(6) Uani 1 1 d . . . . .
H8 H 0.3462 0.5285 0.6858 0.081 Uiso 1 1 calc R . . . .
C9 C 0.5749(3) 0.5843(3) 0.7120(2) 0.0838(8) Uani 1 1 d . . . . .
H9 H 0.5906 0.5818 0.6500 0.101 Uiso 1 1 calc R . . . .
C10 C 0.6978(3) 0.6206(3) 0.7825(3) 0.0864(8) Uani 1 1 d . . . . .
H10 H 0.7967 0.6442 0.7683 0.104 Uiso 1 1 calc R . . . .
C11 C 0.6746(3) 0.6219(3) 0.8730(2) 0.0787(7) Uani 1 1 d . . . . .
H11 H 0.7574 0.6449 0.9202 0.094 Uiso 1 1 calc R . . . .
C12 C 0.5286(3) 0.5892(3) 0.89468(17) 0.0671(6) Uani 1 1 d . . . . .
H12 H 0.5137 0.5914 0.9567 0.081 Uiso 1 1 calc R . . . .
C13 C 0.0740(2) 0.4038(2) 0.75003(15) 0.0570(5) Uani 1 1 d . . . . .
C14 C 0.0082(3) 0.4730(3) 0.70187(17) 0.0661(6) Uani 1 1 d . . . . .
H14 H 0.0380 0.5785 0.7263 0.079 Uiso 1 1 calc R . . . .
C15 C -0.1021(3) 0.3919(3) 0.61746(18) 0.0695(6) Uani 1 1 d . . . . .
H15 H -0.1440 0.4431 0.5868 0.083 Uiso 1 1 calc R . . . .
C16 C -0.1479(2) 0.2361(2) 0.58038(16) 0.0583(5) Uani 1 1 d . . . . .
C17 C -0.0811(2) 0.1590(2) 0.62626(15) 0.0532(5) Uani 1 1 d . . . . .
C18 C 0.0295(2) 0.2418(2) 0.71136(15) 0.0552(5) Uani 1 1 d . . . . .
C19 C 0.0886(3) 0.1548(3) 0.75280(18) 0.0684(6) Uani 1 1 d . . . . .
H19 H 0.1624 0.2035 0.8087 0.082 Uiso 1 1 calc R . . . .
C20 C 0.0380(3) 0.0009(3) 0.71129(19) 0.0754(7) Uani 1 1 d . . . . .
H20 H 0.0760 -0.0566 0.7382 0.091 Uiso 1 1 calc R . . . .
C21 C -0.0735(3) -0.0696(3) 0.62632(17) 0.0628(5) Uani 1 1 d . . . . .
C22 C -0.2362(3) -0.2993(3) 0.50413(18) 0.0767(7) Uani 1 1 d . . . . .
H22A H -0.1956 -0.2552 0.4544 0.115 Uiso 1 1 calc GR . . . .
H22B H -0.3276 -0.2854 0.5151 0.115 Uiso 1 1 calc GR . . . .
H22C H -0.2628 -0.4080 0.4857 0.115 Uiso 1 1 calc GR . . . .
C23 C -0.3509(3) 0.1722(3) 0.44111(17) 0.0640(6) Uani 1 1 d . . . . .
C24 C -0.4538(2) 0.0400(3) 0.35647(16) 0.0600(5) Uani 1 1 d . . . . .
C25 C -0.4418(3) -0.0980(3) 0.3282(2) 0.0876(8) Uani 1 1 d . . . . .
H25 H -0.3677 -0.1133 0.3633 0.105 Uiso 1 1 calc R . . . .
C26 C -0.5393(4) -0.2129(3) 0.2483(2) 0.1020(10) Uani 1 1 d . . . . .
H26 H -0.5299 -0.3048 0.2296 0.122 Uiso 1 1 calc R . . . .
C27 C -0.6496(3) -0.1925(4) 0.1967(2) 0.0906(9) Uani 1 1 d . . . . .
H27 H -0.7159 -0.2707 0.1433 0.109 Uiso 1 1 calc R . . . .
C28 C -0.6619(3) -0.0567(4) 0.2237(2) 0.0821(8) Uani 1 1 d . . . . .
H28 H -0.7363 -0.0422 0.1882 0.099 Uiso 1 1 calc R . . . .
C29 C -0.5648(3) 0.0593(3) 0.30323(18) 0.0689(6) Uani 1 1 d . . . . .
H29 H -0.5743 0.1513 0.3210 0.083 Uiso 1 1 calc R . . . .
N1 N -0.1309(2) 0.0035(2) 0.58461(13) 0.0570(4) Uani 1 1 d . . . . .
N2 N -0.2569(2) 0.1410(2) 0.49735(14) 0.0653(5) Uani 1 1 d . . . . .
O1 O 0.1900(2) 0.4326(2) 0.93411(12) 0.0783(5) Uani 1 1 d . . . . .
O2 O -0.1205(2) -0.22363(18) 0.58969(13) 0.0769(5) Uani 1 1 d . . . . .
O3 O -0.3527(3) 0.2979(2) 0.45708(15) 0.1004(7) Uani 1 1 d . . . . .
P1 P 0.21614(6) 0.51343(7) 0.85862(4) 0.05862(19) Uani 1 1 d . . . . .
H2A H -0.262(3) 0.051(3) 0.4865(17) 0.066(7) Uiso 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 C2 1.396(3) . ?
C1 C6 1.379(3) . ?
C1 P1 1.804(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 C12 1.389(3) . ?
C7 P1 1.806(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.361(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 C18 1.433(3) . ?
C13 P1 1.808(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.402(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C16 C17 1.421(3) . ?
C16 N2 1.398(3) . ?
C17 C18 1.411(3) . ?
C17 N1 1.374(3) . ?
C18 C19 1.422(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.411(3) . ?
C21 N1 1.296(3) . ?
C21 O2 1.355(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 O2 1.437(3) . ?
C23 C24 1.501(3) . ?
C23 N2 1.353(3) . ?
C23 O3 1.217(3) . ?
C24 C25 1.386(3) . ?
C24 C29 1.378(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.381(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.366(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.380(4) . ?
C29 H29 0.9300 . ?
N2 H2A 0.84(2) . ?
O1 P1 1.4855(17) . ?

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
C2 C1 P1 117.62(18) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 P1 123.59(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C12 118.7(2) . . ?
C8 C7 P1 123.18(17) . . ?
C12 C7 P1 118.13(17) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 118.4(2) . . ?
C14 C13 P1 121.29(17) . . ?
C18 C13 P1 120.34(16) . . ?
C13 C14 H14 118.6 . . ?
C13 C14 C15 122.9(2) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 N2 125.5(2) . . ?
N2 C16 C17 114.42(19) . . ?
C18 C17 C16 119.97(19) . . ?
N1 C17 C16 116.97(19) . . ?
N1 C17 C18 123.06(19) . . ?
C17 C18 C13 119.26(19) . . ?
C17 C18 C19 116.0(2) . . ?
C19 C18 C13 124.7(2) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.8 . . ?
C19 C20 C21 118.5(2) . . ?
C21 C20 H20 120.8 . . ?
N1 C21 C20 124.1(2) . . ?
N1 C21 O2 120.6(2) . . ?
O2 C21 C20 115.3(2) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
N2 C23 C24 115.08(19) . . ?
O3 C23 C24 121.9(2) . . ?
O3 C23 N2 123.0(2) . . ?
C25 C24 C23 124.0(2) . . ?
C29 C24 C23 117.4(2) . . ?
C29 C24 C25 118.6(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.3(3) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.2 . . ?
C26 C27 C28 119.7(3) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 120.5(2) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C21 N1 C17 117.93(19) . . ?
C16 N2 H2A 109.0(16) . . ?
C23 N2 C16 130.0(2) . . ?
C23 N2 H2A 120.9(16) . . ?
C21 O2 C22 116.59(18) . . ?
C1 P1 C7 106.06(10) . . ?
C1 P1 C13 107.00(10) . . ?
C7 P1 C13 105.63(10) . . ?
O1 P1 C1 111.87(10) . . ?
O1 P1 C7 112.40(10) . . ?
O1 P1 C13 113.36(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A N1 0.84(2) 2.11(2) 2.622(3) 119(2) .


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20170442
_database_code_depnum_ccdc_archive 'CCDC 1543497'
_audit_update_record             
;
2017-04-11 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N2 O2 P'
_chemical_formula_sum            'C28 H21 N2 O2 P'
_chemical_formula_weight         448.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H70N2OS1F2
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.9961(5)
_cell_length_b                   8.6310(3)
_cell_length_c                   21.6563(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.014(4)
_cell_angle_gamma                90
_cell_volume                     2233.68(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5200
_cell_measurement_theta_min      4.1000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8345
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.087
_diffrn_reflns_theta_max         67.087
_diffrn_reflns_theta_min         3.699
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega   66.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   63.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   61.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega  -30.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  8 omega   58.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   14.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 10 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   42.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   66.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   81.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 60

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  114.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   89.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega  118.00  146.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   51.00  125.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 19 omega   50.00  163.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1172872000
_diffrn_orient_matrix_UB_12      -0.0218074000
_diffrn_orient_matrix_UB_13      0.0339732000
_diffrn_orient_matrix_UB_21      -0.0536532000
_diffrn_orient_matrix_UB_22      -0.0609586000
_diffrn_orient_matrix_UB_23      0.0574224000
_diffrn_orient_matrix_UB_31      0.0042792000
_diffrn_orient_matrix_UB_32      -0.1662412000
_diffrn_orient_matrix_UB_33      -0.0254576000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3377
_reflns_number_total             3994
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.5200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25),
  C26(H26), C27(H27), C28(H28), N1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.69349(15) -0.0621(2) 0.41360(9) 0.0363(4) Uani 1 1 d . . . . .
C2 C 0.74927(17) -0.1984(2) 0.40237(10) 0.0460(5) Uani 1 1 d . . . . .
H2 H 0.7869 -0.2079 0.3668 0.055 Uiso 1 1 calc R . . . .
C3 C 0.7493(2) -0.3204(3) 0.44382(12) 0.0565(6) Uani 1 1 d . . . . .
H3 H 0.7884 -0.4107 0.4366 0.068 Uiso 1 1 calc R . . . .
C4 C 0.6919(2) -0.3085(3) 0.49520(13) 0.0620(7) Uani 1 1 d . . . . .
H4 H 0.6901 -0.3920 0.5223 0.074 Uiso 1 1 calc R . . . .
C5 C 0.6366(2) -0.1737(3) 0.50727(12) 0.0671(7) Uani 1 1 d . . . . .
H5 H 0.5985 -0.1659 0.5427 0.080 Uiso 1 1 calc R . . . .
C6 C 0.63756(19) -0.0494(3) 0.46686(11) 0.0545(6) Uani 1 1 d . . . . .
H6 H 0.6009 0.0421 0.4754 0.065 Uiso 1 1 calc R . . . .
C7 C 0.82258(15) 0.2106(2) 0.39351(9) 0.0367(4) Uani 1 1 d . . . . .
C8 C 0.8664(2) 0.2013(3) 0.45420(11) 0.0603(6) Uani 1 1 d . . . . .
H8 H 0.8316 0.1400 0.4822 0.072 Uiso 1 1 calc R . . . .
C9 C 0.9623(2) 0.2833(4) 0.47368(13) 0.0750(8) Uani 1 1 d . . . . .
H9 H 0.9918 0.2760 0.5147 0.090 Uiso 1 1 calc R . . . .
C10 C 1.0141(2) 0.3744(3) 0.43345(14) 0.0648(7) Uani 1 1 d . . . . .
H10 H 1.0785 0.4289 0.4470 0.078 Uiso 1 1 calc R . . . .
C11 C 0.97070(19) 0.3852(3) 0.37297(13) 0.0587(6) Uani 1 1 d . . . . .
H11 H 1.0054 0.4477 0.3454 0.070 Uiso 1 1 calc R . . . .
C12 C 0.87539(17) 0.3032(2) 0.35299(11) 0.0473(5) Uani 1 1 d . . . . .
H12 H 0.8465 0.3104 0.3118 0.057 Uiso 1 1 calc R . . . .
C13 C 0.58167(15) 0.2162(2) 0.36134(8) 0.0338(4) Uani 1 1 d . . . . .
C14 C 0.58682(16) 0.3558(2) 0.39131(9) 0.0417(5) Uani 1 1 d . . . . .
H14 H 0.6514 0.3807 0.4163 0.050 Uiso 1 1 calc R . . . .
C15 C 0.49838(17) 0.4630(2) 0.38589(10) 0.0438(5) Uani 1 1 d . . . . .
H15 H 0.5047 0.5565 0.4073 0.053 Uiso 1 1 calc R . . . .
C16 C 0.40311(15) 0.4295(2) 0.34904(9) 0.0354(4) Uani 1 1 d . . . . .
C17 C 0.38944(15) 0.2811(2) 0.31971(8) 0.0334(4) Uani 1 1 d . . . . .
C18 C 0.47977(14) 0.1736(2) 0.32600(8) 0.0326(4) Uani 1 1 d . . . . .
C19 C 0.46411(16) 0.0252(2) 0.29794(9) 0.0410(4) Uani 1 1 d . . . . .
H19 H 0.5223 -0.0463 0.3016 0.049 Uiso 1 1 calc R . . . .
C20 C 0.36553(18) -0.0138(2) 0.26585(10) 0.0471(5) Uani 1 1 d . . . . .
H20 H 0.3565 -0.1117 0.2482 0.057 Uiso 1 1 calc R . . . .
C21 C 0.27738(18) 0.0940(3) 0.25941(10) 0.0488(5) Uani 1 1 d . . . . .
H21 H 0.2107 0.0673 0.2368 0.059 Uiso 1 1 calc R . . . .
C22 C 0.28850(16) 0.2366(2) 0.28588(9) 0.0421(5) Uani 1 1 d . . . . .
H22 H 0.2289 0.3058 0.2817 0.050 Uiso 1 1 calc R . . . .
C23 C 0.28724(17) 0.6498(2) 0.37849(9) 0.0427(5) Uani 1 1 d . . . . .
C24 C 0.18728(16) 0.7463(2) 0.35552(9) 0.0382(4) Uani 1 1 d . . . . .
C25 C 0.1712(2) 0.8882(3) 0.38274(11) 0.0530(6) Uani 1 1 d . . . . .
H25 H 0.2225 0.9260 0.4138 0.064 Uiso 1 1 calc R . . . .
C26 C 0.0768(2) 0.9730(3) 0.36278(12) 0.0631(7) Uani 1 1 d . . . . .
H26 H 0.0636 1.0689 0.3803 0.076 Uiso 1 1 calc R . . . .
C27 C 0.00288(19) 0.9137(3) 0.31683(12) 0.0563(6) Uani 1 1 d . . . . .
H27 H -0.0614 0.9678 0.3028 0.068 Uiso 1 1 calc R . . . .
C28 C 0.02663(17) 0.7727(3) 0.29234(12) 0.0540(6) Uani 1 1 d . . . . .
H28 H -0.0233 0.7330 0.2610 0.065 Uiso 1 1 calc R . . . .
N1 N 0.31509(13) 0.53826(19) 0.33879(8) 0.0408(4) Uani 1 1 d . . . . .
H1 H 0.2754 0.5328 0.3038 0.049 Uiso 1 1 calc R . . . .
N2 N 0.11703(13) 0.6880(2) 0.31046(9) 0.0461(4) Uani 1 1 d . . . . .
O1 O 0.72650(11) 0.04376(17) 0.29721(6) 0.0423(3) Uani 1 1 d . . . . .
O2 O 0.33411(16) 0.6725(2) 0.42975(7) 0.0711(6) Uani 1 1 d . . . . .
P1 P 0.70509(4) 0.09650(5) 0.36057(2) 0.03258(15) 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 C2 1.385(3) . ?
C1 C6 1.389(3) . ?
C1 P1 1.8002(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(3) . ?
C7 C12 1.381(3) . ?
C7 P1 1.8139(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(3) . ?
C13 C18 1.432(2) . ?
C13 P1 1.8068(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.405(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(3) . ?
C16 C17 1.433(2) . ?
C16 N1 1.416(2) . ?
C17 C18 1.424(2) . ?
C17 C22 1.413(3) . ?
C18 C19 1.423(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.361(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.406(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.360(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.508(3) . ?
C23 N1 1.352(3) . ?
C23 O2 1.216(2) . ?
C24 C25 1.380(3) . ?
C24 N2 1.331(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.372(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.368(3) . ?
C28 H28 0.9300 . ?
C28 N2 1.338(3) . ?
N1 H1 0.8600 . ?
O1 P1 1.4890(14) . ?

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
C2 C1 C6 119.26(19) . . ?
C2 C1 P1 117.92(15) . . ?
C6 C1 P1 122.67(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C12 118.91(19) . . ?
C8 C7 P1 124.27(17) . . ?
C12 C7 P1 116.63(15) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 120.7(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 118.75(16) . . ?
C14 C13 P1 120.34(14) . . ?
C18 C13 P1 120.66(13) . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.57(17) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.75(18) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.38(17) . . ?
C15 C16 N1 121.70(17) . . ?
N1 C16 C17 117.92(16) . . ?
C18 C17 C16 118.92(16) . . ?
C22 C17 C16 122.21(17) . . ?
C22 C17 C18 118.86(17) . . ?
C17 C18 C13 119.35(16) . . ?
C19 C18 C13 122.29(16) . . ?
C19 C18 C17 118.34(16) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.16(18) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.97(19) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.79(19) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.87(18) . . ?
C21 C22 H22 119.6 . . ?
N1 C23 C24 114.63(17) . . ?
O2 C23 C24 120.25(18) . . ?
O2 C23 N1 125.09(19) . . ?
C25 C24 C23 119.07(19) . . ?
N2 C24 C23 117.89(17) . . ?
N2 C24 C25 123.02(19) . . ?
C24 C25 H25 120.8 . . ?
C24 C25 C26 118.5(2) . . ?
C26 C25 H25 120.8 . . ?
C25 C26 H26 120.4 . . ?
C27 C26 C25 119.2(2) . . ?
C27 C26 H26 120.4 . . ?
C26 C27 H27 121.0 . . ?
C28 C27 C26 118.0(2) . . ?
C28 C27 H27 121.0 . . ?
C27 C28 H28 117.9 . . ?
N2 C28 C27 124.3(2) . . ?
N2 C28 H28 117.9 . . ?
C16 N1 H1 116.8 . . ?
C23 N1 C16 126.49(17) . . ?
C23 N1 H1 116.8 . . ?
C24 N2 C28 117.00(19) . . ?
C1 P1 C7 105.25(9) . . ?
C1 P1 C13 108.66(9) . . ?
C13 P1 C7 107.16(8) . . ?
O1 P1 C1 112.61(9) . . ?
O1 P1 C7 109.74(8) . . ?
O1 P1 C13 113.00(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 2.19 2.944(2) 146.6 2_655

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
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C1 P1 C7 -92.44(16) . . . . ?
C2 C1 P1 C13 153.06(15) . . . . ?
C2 C1 P1 O1 27.09(18) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 P1 C7 83.19(19) . . . . ?
C6 C1 P1 C13 -31.3(2) . . . . ?
C6 C1 P1 O1 -157.29(17) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C7 P1 C1 -18.0(2) . . . . ?
C8 C7 P1 C13 97.5(2) . . . . ?
C8 C7 P1 O1 -139.42(19) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?
C12 C7 P1 C1 156.83(15) . . . . ?
C12 C7 P1 C13 -87.62(16) . . . . ?
C12 C7 P1 O1 35.42(18) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C13 C18 C19 C20 178.40(19) . . . . ?
C14 C13 C18 C17 4.0(3) . . . . ?
C14 C13 C18 C19 -174.40(18) . . . . ?
C14 C13 P1 C1 104.77(17) . . . . ?
C14 C13 P1 C7 -8.47(19) . . . . ?
C14 C13 P1 O1 -129.48(16) . . . . ?
C14 C15 C16 C17 4.8(3) . . . . ?
C14 C15 C16 N1 -175.56(19) . . . . ?
C15 C16 C17 C18 -4.4(3) . . . . ?
C15 C16 C17 C22 174.17(19) . . . . ?
C15 C16 N1 C23 -29.7(3) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C16 C17 C18 C19 178.46(17) . . . . ?
C16 C17 C22 C21 -178.9(2) . . . . ?
C17 C16 N1 C23 150.0(2) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C13 C14 C15 -3.8(3) . . . . ?
C18 C13 P1 C1 -80.98(16) . . . . ?
C18 C13 P1 C7 165.77(15) . . . . ?
C18 C13 P1 O1 44.76(17) . . . . ?
C18 C17 C22 C21 -0.3(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C17 1.0(3) . . . . ?
C22 C17 C18 C13 -178.65(17) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C23 C24 C25 C26 -177.6(2) . . . . ?
C23 C24 N2 C28 177.52(18) . . . . ?
C24 C23 N1 C16 -178.46(17) . . . . ?
C24 C25 C26 C27 -0.1(4) . . . . ?
C25 C24 N2 C28 -1.0(3) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C26 C27 C28 N2 0.4(4) . . . . ?
C27 C28 N2 C24 0.3(3) . . . . ?
N1 C16 C17 C18 175.91(16) . . . . ?
N1 C16 C17 C22 -5.5(3) . . . . ?
N1 C23 C24 C25 -161.3(2) . . . . ?
N1 C23 C24 N2 20.1(3) . . . . ?
N2 C24 C25 C26 0.9(3) . . . . ?
O2 C23 C24 C25 20.7(3) . . . . ?
O2 C23 C24 N2 -157.9(2) . . . . ?
O2 C23 N1 C16 -0.5(4) . . . . ?
P1 C1 C2 C3 175.77(16) . . . . ?
P1 C1 C6 C5 -176.75(19) . . . . ?
P1 C7 C8 C9 174.3(2) . . . . ?
P1 C7 C12 C11 -175.11(17) . . . . ?
P1 C13 C14 C15 170.52(17) . . . . ?
P1 C13 C18 C17 -170.30(13) . . . . ?
P1 C13 C18 C19 11.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
