# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_17070501
_database_code_depnum_ccdc_archive 'CCDC 1587616'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ONdP(BC)
_chemical_formula_moiety         'C37 H28 N O P'
_chemical_formula_sum            'C37 H28 N O P'
_chemical_formula_weight         533.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOP
_chemical_oxdiff_usercomment     ONdP-M
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        P21/n
_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                   21.3348(9)
_cell_length_b                   5.9392(2)
_cell_length_c                   23.3779(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.485(4)
_cell_angle_gamma                90
_cell_volume                     2892.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4174
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9460
_cell_measurement_theta_min      3.8470
_shelx_estimated_absorpt_T_max   0.792
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10043
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.365
_diffrn_reflns_theta_min         3.873
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  14.00   1.00    1.00    --  -38.50   0.00-150.00  101
  2  ω     23.00  97.00   1.00    1.00    --   43.31-125.00 150.00   74
  3  ω     43.00 132.00   1.00    2.00    --  108.63 -77.00 -60.00   89
  4  ω    108.00 177.00   1.00    2.00    --  108.63  30.00 120.00   69
  5  ω    102.00 153.00   1.00    2.00    --  108.63 115.00 128.00   51
  6  ω     82.00 177.00   1.00    2.00    --  108.63  77.00  60.00   95
  7  ω     83.00 177.00   1.00    2.00    --  108.63  61.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0281530000
_diffrn_orient_matrix_UB_12      0.2397641000
_diffrn_orient_matrix_UB_13      -0.0069552000
_diffrn_orient_matrix_UB_21      -0.0235901000
_diffrn_orient_matrix_UB_22      -0.0396195000
_diffrn_orient_matrix_UB_23      -0.0663031000
_diffrn_orient_matrix_UB_31      -0.0642237000
_diffrn_orient_matrix_UB_32      -0.0903852000
_diffrn_orient_matrix_UB_33      0.0105757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5013
_reflns_number_total             5719
_reflns_odcompleteness_completeness 98.67
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5719
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.1587
_refine_ls_R_factor_gt           0.1496
_refine_ls_restrained_S_all      1.078
_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)+(0.0632P)²+26.3920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3314
_refine_ls_wR_factor_ref         0.3358
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C18A-C17A \\sim C19-C18A \\sim C17-C16 \\sim C16-C15 \\sim C19-C14A \\sim
C19-C14 \\sim C16A-C15A ~
 C17A-C16A \\sim C18-C17 \\sim C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 C31-C30 \\sim C31-C26 \\sim C27-C26 \\sim C28-C27 \\sim C29-C28 \\sim C30-C29
 with sigma of 0.02
3. Rigid bond restraints
 C30, C31, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C18A) = Uanis(C18) = Uanis(C17A) = Uanis(C17) = Uanis(C16A) = Uanis(C16)
= Uanis(C15) = Uanis(C15A) = Uanis(C14A) = Uanis(C14)
5. Others
 Sof(P2)=Sof(N2)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=
 Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=1-FVAR(1)
 Sof(P1)=Sof(C18)=Sof(H18)=Sof(N1)=Sof(C16)=Sof(H16)=Sof(C14)=Sof(H14)=
 Sof(C17)=Sof(H17)=Sof(C15)=Sof(H15)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C7(H7), C25(H25), C22(H22), C9(H9), C27(H27), C24(H24), C3(H3),
 C6(H6), C37(H37), C11(H11), C12(H12), C18(H18), C30(H30), C34(H34), C35(H35),
 C4(H4), C13(H13), C33(H33), C10(H10), C31(H31), C16(H16), C36(H36), C28(H28),
 C29(H29), C14(H14), C17(H17), C15(H15), C18A(H18A), C17A(H17A), C16A(H16A),
 C15A(H15A), C14A(H14A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
P1 P 0.08232(9) 0.6369(4) 0.63311(8) 0.0270(6) Uani 0.701(4) 1 d . . P A 1
O1 O 0.2508(2) -0.0978(7) 0.4996(3) 0.0612(16) Uani 1 1 d . . . . .
C20 C 0.2080(2) 0.2366(9) 0.5293(2) 0.0242(10) Uani 1 1 d . . . . .
C21 C 0.2249(2) 0.4445(9) 0.5556(2) 0.0285(11) Uani 1 1 d . . . . .
H21 H 0.2630 0.5129 0.5517 0.034 Uiso 1 1 calc R . . . .
C1 C 0.2506(2) 0.1103(9) 0.4981(2) 0.0291(12) Uani 1 1 d . . . . .
C7 C 0.2783(2) 0.4361(10) 0.4390(2) 0.0320(12) Uani 1 1 d . . . . .
H7 H 0.2416 0.5123 0.4437 0.038 Uiso 1 1 calc R . . . .
C2 C 0.2934(2) 0.2296(10) 0.4661(2) 0.0280(11) Uani 1 1 d . . . . .
C25 C 0.1508(2) 0.1349(9) 0.5358(2) 0.0294(11) Uani 1 1 d . . . . .
H25 H 0.1390 -0.0048 0.5189 0.035 Uiso 1 1 calc R . . . .
C22 C 0.1861(3) 0.5500(11) 0.5873(2) 0.0368(14) Uani 1 1 d . . . . .
H22 H 0.1985 0.6889 0.6044 0.044 Uiso 1 1 calc R . . . .
C26 C 0.1266(3) 0.5881(10) 0.7053(3) 0.0386(14) Uani 1 1 d D U . . .
C9 C 0.5003(3) 0.3087(12) 0.3288(3) 0.0405(15) Uani 1 1 d . . . . .
H9 H 0.4726 0.2810 0.2929 0.049 Uiso 1 1 calc R . . . .
C27 C 0.1710(3) 0.4211(11) 0.7255(2) 0.0365(13) Uani 1 1 d D . . . .
H27 H 0.1759 0.3082 0.6992 0.044 Uiso 1 1 calc R . . . .
C19 C 0.3812(3) 0.5954(11) 0.3007(3) 0.0413(15) Uani 1 1 d D . . . .
C24 C 0.1118(3) 0.2418(13) 0.5675(3) 0.0420(15) Uani 1 1 d . . . . .
H24 H 0.0737 0.1735 0.5713 0.050 Uiso 1 1 calc R . . . .
C3 C 0.3493(3) 0.1203(11) 0.4588(3) 0.0378(14) Uani 1 1 d . . . . .
H3 H 0.3601 -0.0178 0.4770 0.045 Uiso 1 1 calc R . . . .
C6 C 0.3171(3) 0.5296(12) 0.4052(3) 0.0439(16) Uani 1 1 d . . . . .
H6 H 0.3061 0.6680 0.3873 0.053 Uiso 1 1 calc R . . . .
C37 C 0.0065(3) 0.2757(13) 0.6678(3) 0.0456(16) Uani 1 1 d . . . . .
H37 H 0.0390 0.2430 0.7002 0.055 Uiso 1 1 calc R . . . .
C32 C 0.0152(3) 0.4439(12) 0.6297(2) 0.0409(15) Uani 1 1 d . . . . .
C23 C 0.1288(3) 0.4540(13) 0.5942(3) 0.0428(16) Uani 1 1 d . . . . .
C11 C 0.6030(3) 0.2592(14) 0.3929(3) 0.0486(18) Uani 1 1 d . . . . .
H11 H 0.6436 0.1943 0.4010 0.058 Uiso 1 1 calc R . . . .
C8 C 0.4805(3) 0.4377(13) 0.3696(2) 0.0445(17) Uani 1 1 d . . . . .
C12 C 0.5842(3) 0.3954(13) 0.4333(3) 0.0469(16) Uani 1 1 d . . . . .
H12 H 0.6127 0.4277 0.4685 0.056 Uiso 1 1 calc R . . . .
C18 C 0.3284(6) 0.491(2) 0.2690(5) 0.0532(12) Uani 0.701(4) 1 d D . P A 1
H18 H 0.3100 0.3634 0.2817 0.064 Uiso 0.701(4) 1 calc R . P A 1
N1 N 0.4121(3) 0.4856(13) 0.3589(3) 0.0315(15) Uani 0.701(4) 1 d . . P A 1
C30 C 0.1636(3) 0.7405(13) 0.8052(3) 0.0515(17) Uani 1 1 d D U . . .
H30 H 0.1620 0.8531 0.8325 0.062 Uiso 1 1 calc R . . . .
C34 C -0.0910(3) 0.3694(13) 0.5730(3) 0.0513(18) Uani 1 1 d . . . . .
H34 H -0.1233 0.3991 0.5402 0.062 Uiso 1 1 calc R . . . .
C5 C 0.3732(3) 0.4192(15) 0.3974(3) 0.055(2) Uani 1 1 d . . . . .
C35 C -0.0991(3) 0.2027(15) 0.6106(3) 0.054(2) Uani 1 1 d . . . . .
H35 H -0.1372 0.1212 0.6045 0.064 Uiso 1 1 calc R . . . .
C4 C 0.3887(3) 0.2108(15) 0.4255(3) 0.053(2) Uani 1 1 d . . . . .
H4 H 0.4256 0.1345 0.4216 0.063 Uiso 1 1 calc R . . . .
C13 C 0.5234(4) 0.4845(16) 0.4222(3) 0.064(2) Uani 1 1 d . . . . .
H13 H 0.5108 0.5765 0.4499 0.077 Uiso 1 1 calc R . . . .
C33 C -0.0361(4) 0.4929(15) 0.5828(3) 0.061(2) Uani 1 1 d . . . . .
H33 H -0.0325 0.6123 0.5580 0.073 Uiso 1 1 calc R . . . .
C10 C 0.5613(3) 0.2192(15) 0.3403(3) 0.062(2) Uani 1 1 d . . . . .
H10 H 0.5743 0.1307 0.3122 0.074 Uiso 1 1 calc R . . . .
C31 C 0.1237(4) 0.7560(13) 0.7493(3) 0.067(2) Uani 1 1 d D U . . .
H31 H 0.0951 0.8755 0.7404 0.080 Uiso 1 1 calc R . . . .
C16 C 0.3332(5) 0.784(2) 0.1949(5) 0.0532(12) Uani 0.701(4) 1 d D . P A 1
H16 H 0.3159 0.8522 0.1591 0.064 Uiso 0.701(4) 1 calc R . P A 1
C36 C -0.0499(4) 0.1563(16) 0.6583(3) 0.066(3) Uani 1 1 d . . . . .
H36 H -0.0551 0.0426 0.6842 0.080 Uiso 1 1 calc R . . . .
C28 C 0.2081(3) 0.4087(17) 0.7808(3) 0.063(2) Uani 1 1 d D . . . .
H28 H 0.2365 0.2891 0.7911 0.076 Uiso 1 1 calc R . . . .
C29 C 0.2040(4) 0.5675(14) 0.8204(4) 0.069(2) Uani 1 1 d D . . . .
H29 H 0.2290 0.5579 0.8582 0.083 Uiso 1 1 calc R . . . .
C14 C 0.4151(4) 0.7734(18) 0.2855(4) 0.0532(12) Uani 0.701(4) 1 d D . P A 1
H14 H 0.4522 0.8281 0.3099 0.064 Uiso 0.701(4) 1 calc R . P A 1
C17 C 0.3044(5) 0.599(2) 0.2145(4) 0.0532(12) Uani 0.701(4) 1 d D . P A 1
H17 H 0.2673 0.5415 0.1905 0.064 Uiso 0.701(4) 1 calc R . P A 1
C15 C 0.3898(4) 0.865(2) 0.2316(4) 0.0532(12) Uani 0.701(4) 1 d D . P A 1
H15 H 0.4110 0.9850 0.2187 0.064 Uiso 0.701(4) 1 calc R . P A 1
P2 P 0.4180(2) 0.6662(8) 0.36544(19) 0.0282(13) Uani 0.299(4) 1 d . . P A 2
N2 N 0.0881(8) 0.465(3) 0.6396(7) 0.039(4) Uani 0.299(4) 1 d . . P A 2
C18A C 0.3333(13) 0.442(4) 0.2744(11) 0.0532(12) Uani 0.299(4) 1 d D . P A 2
H18A H 0.3264 0.3277 0.2995 0.064 Uiso 0.299(4) 1 calc R . P A 2
C17A C 0.2937(10) 0.427(4) 0.2182(8) 0.0532(12) Uani 0.299(4) 1 d D . P A 2
H17A H 0.2655 0.3072 0.2082 0.064 Uiso 0.299(4) 1 calc R . P A 2
C16A C 0.2974(10) 0.596(4) 0.1774(9) 0.0532(12) Uani 0.299(4) 1 d D . P A 2
H16A H 0.2705 0.5962 0.1403 0.064 Uiso 0.299(4) 1 calc R . P A 2
C15A C 0.3433(12) 0.764(5) 0.1951(10) 0.0532(12) Uani 0.299(4) 1 d D . P A 2
H15A H 0.3530 0.8708 0.1692 0.064 Uiso 0.299(4) 1 calc R . P A 2
C14A C 0.3737(11) 0.760(4) 0.2545(8) 0.0532(12) Uani 0.299(4) 1 d D . P A 2
H14A H 0.3937 0.8958 0.2671 0.064 Uiso 0.299(4) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C26 1.771(6) . ?
P1 C32 1.822(7) . ?
P1 C23 1.839(6) . ?
O1 C1 1.236(7) . ?
C20 C21 1.392(7) . ?
C20 C1 1.486(7) . ?
C20 C25 1.400(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(8) . ?
C1 C2 1.479(7) . ?
C7 H7 0.9300 . ?
C7 C2 1.386(8) . ?
C7 C6 1.379(8) . ?
C2 C3 1.402(7) . ?
C25 H25 0.9300 . ?
C25 C24 1.381(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(9) . ?
C26 C27 1.381(7) . ?
C26 C31 1.443(9) . ?
C26 N2 1.738(19) . ?
C9 H9 0.9300 . ?
C9 C8 1.360(9) . ?
C9 C10 1.377(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.366(7) . ?
C19 C18 1.357(14) . ?
C19 N1 1.525(9) . ?
C19 C14 1.369(10) . ?
C19 P2 1.604(8) . ?
C19 C18A 1.406(14) . ?
C19 C14A 1.439(14) . ?
C24 H24 0.9300 . ?
C24 C23 1.419(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.411(10) . ?
C37 H37 0.9300 . ?
C37 C32 1.378(9) . ?
C37 C36 1.373(9) . ?
C32 C33 1.402(9) . ?
C32 N2 1.527(17) . ?
C23 N2 1.511(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(10) . ?
C11 C10 1.374(9) . ?
C8 N1 1.455(8) . ?
C8 C13 1.393(9) . ?
C8 P2 1.890(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.420(10) . ?
N1 C5 1.406(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.401(9) . ?
C30 C29 1.339(9) . ?
C34 H34 0.9300 . ?
C34 C35 1.360(11) . ?
C34 C33 1.359(10) . ?
C5 C4 1.407(11) . ?
C5 P2 1.983(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.383(10) . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C33 H33 0.9300 . ?
C10 H10 0.9300 . ?
C31 H31 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.387(12) . ?
C16 C15 1.405(11) . ?
C36 H36 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.337(9) . ?
C29 H29 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.371(10) . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C18A H18A 0.9300 . ?
C18A C17A 1.404(14) . ?
C17A H17A 0.9300 . ?
C17A C16A 1.395(15) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.398(15) . ?
C15A H15A 0.9300 . ?
C15A C14A 1.401(14) . ?
C14A H14A 0.9300 . ?

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
C26 P1 C32 101.0(3) . . ?
C26 P1 C23 98.1(3) . . ?
C32 P1 C23 96.3(3) . . ?
C21 C20 C1 122.4(5) . . ?
C21 C20 C25 119.0(5) . . ?
C25 C20 C1 118.5(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(5) . . ?
C22 C21 H21 119.6 . . ?
O1 C1 C20 119.4(5) . . ?
O1 C1 C2 119.6(5) . . ?
C2 C1 C20 121.0(5) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C2 120.6(5) . . ?
C7 C2 C1 123.2(5) . . ?
C7 C2 C3 118.3(5) . . ?
C3 C2 C1 118.3(5) . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 120.0(5) . . ?
C24 C25 H25 120.0 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.5(6) . . ?
C23 C22 H22 119.2 . . ?
C27 C26 P1 128.8(5) . . ?
C27 C26 C31 112.7(6) . . ?
C27 C26 N2 99.0(8) . . ?
C31 C26 P1 118.0(5) . . ?
C31 C26 N2 146.6(8) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C26 C27 H27 117.4 . . ?
C28 C27 C26 125.2(7) . . ?
C28 C27 H27 117.4 . . ?
C18 C19 N1 116.0(7) . . ?
C18 C19 C14 129.4(8) . . ?
C14 C19 N1 114.2(6) . . ?
C18A C19 P2 137.9(12) . . ?
C18A C19 C14A 99.2(16) . . ?
C14A C19 P2 118.8(11) . . ?
C25 C24 H24 119.4 . . ?
C25 C24 C23 121.2(5) . . ?
C23 C24 H24 119.4 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(6) . . ?
C4 C3 H3 119.0 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C5 121.3(6) . . ?
C5 C6 H6 119.4 . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C36 C37 C32 120.4(6) . . ?
C37 C32 P1 129.9(5) . . ?
C37 C32 C33 117.7(6) . . ?
C37 C32 N2 103.7(8) . . ?
C33 C32 P1 112.2(5) . . ?
C33 C32 N2 134.4(8) . . ?
C22 C23 P1 113.4(5) . . ?
C22 C23 C24 117.5(5) . . ?
C22 C23 N2 135.9(9) . . ?
C24 C23 P1 128.9(5) . . ?
C24 C23 N2 102.5(9) . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
C9 C8 N1 116.2(6) . . ?
C9 C8 C13 119.2(6) . . ?
C9 C8 P2 133.7(5) . . ?
C13 C8 N1 123.8(6) . . ?
C13 C8 P2 102.9(5) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C19 C18 H18 123.9 . . ?
C19 C18 C17 112.3(11) . . ?
C17 C18 H18 123.9 . . ?
C8 N1 C19 117.5(5) . . ?
C5 N1 C19 119.4(5) . . ?
C5 N1 C8 122.9(6) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C29 C30 C31 121.6(7) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C33 C34 C35 120.5(6) . . ?
C6 C5 P2 101.4(5) . . ?
N1 C5 C6 126.0(7) . . ?
N1 C5 C4 115.8(7) . . ?
C4 C5 C6 117.9(5) . . ?
C4 C5 P2 138.0(5) . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.1(6) . . ?
C36 C35 H35 120.4 . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(7) . . ?
C12 C13 H13 119.9 . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.3(7) . . ?
C34 C33 H33 119.3 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.6 . . ?
C26 C31 H31 119.7 . . ?
C30 C31 C26 120.5(7) . . ?
C30 C31 H31 119.7 . . ?
C17 C16 H16 121.6 . . ?
C17 C16 C15 116.9(11) . . ?
C15 C16 H16 121.6 . . ?
C37 C36 C35 120.9(7) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(8) . . ?
C29 C28 H28 119.8 . . ?
C30 C29 H29 120.2 . . ?
C28 C29 C30 119.5(8) . . ?
C28 C29 H29 120.2 . . ?
C19 C14 H14 122.6 . . ?
C19 C14 C15 114.7(9) . . ?
C15 C14 H14 122.6 . . ?
C18 C17 H17 118.1 . . ?
C16 C17 C18 123.7(11) . . ?
C16 C17 H17 118.1 . . ?
C16 C15 H15 118.6 . . ?
C14 C15 C16 122.8(11) . . ?
C14 C15 H15 118.6 . . ?
C19 P2 C8 93.2(4) . . ?
C19 P2 C5 89.1(4) . . ?
C8 P2 C5 80.9(4) . . ?
C32 N2 C26 116.1(11) . . ?
C23 N2 C26 113.9(10) . . ?
C23 N2 C32 127.6(12) . . ?
C19 C18A H18A 113.5 . . ?
C17A C18A C19 133(2) . . ?
C17A C18A H18A 113.5 . . ?
C18A C17A H17A 120.6 . . ?
C16A C17A C18A 119(2) . . ?
C16A C17A H17A 120.6 . . ?
C17A C16A H16A 121.6 . . ?
C17A C16A C15A 117(2) . . ?
C15A C16A H16A 121.6 . . ?
C16A C15A H15A 122.4 . . ?
C16A C15A C14A 115(3) . . ?
C14A C15A H15A 122.4 . . ?
C19 C14A H14A 112.5 . . ?
C15A C14A C19 135(2) . . ?
C15A C14A H14A 112.5 . . ?

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
P1 C26 C27 C28 172.7(6) . . . . ?
P1 C26 C31 C30 -172.2(6) . . . . ?
P1 C32 C33 C34 -179.5(7) . . . . ?
O1 C1 C2 C7 149.3(6) . . . . ?
O1 C1 C2 C3 -25.3(9) . . . . ?
C20 C21 C22 C23 0.0(9) . . . . ?
C20 C1 C2 C7 -31.5(8) . . . . ?
C20 C1 C2 C3 153.9(5) . . . . ?
C20 C25 C24 C23 -0.6(9) . . . . ?
C21 C20 C1 O1 146.4(6) . . . . ?
C21 C20 C1 C2 -32.8(7) . . . . ?
C21 C20 C25 C24 0.8(8) . . . . ?
C21 C22 C23 P1 -175.3(4) . . . . ?
C21 C22 C23 C24 0.2(9) . . . . ?
C21 C22 C23 N2 152.6(12) . . . . ?
C1 C20 C21 C22 -175.8(5) . . . . ?
C1 C20 C25 C24 176.2(5) . . . . ?
C1 C2 C3 C4 174.4(6) . . . . ?
C7 C2 C3 C4 -0.5(9) . . . . ?
C7 C6 C5 N1 172.3(7) . . . . ?
C7 C6 C5 C4 -0.5(10) . . . . ?
C7 C6 C5 P2 -165.1(5) . . . . ?
C2 C7 C6 C5 -0.2(9) . . . . ?
C2 C3 C4 C5 -0.2(11) . . . . ?
C25 C20 C21 C22 -0.5(8) . . . . ?
C25 C20 C1 O1 -28.9(8) . . . . ?
C25 C20 C1 C2 151.9(5) . . . . ?
C25 C24 C23 P1 174.8(5) . . . . ?
C25 C24 C23 C22 0.1(9) . . . . ?
C25 C24 C23 N2 -160.6(8) . . . . ?
C22 C23 N2 C26 -13(2) . . . . ?
C22 C23 N2 C32 148.5(12) . . . . ?
C26 P1 C32 C37 -10.7(8) . . . . ?
C26 P1 C32 C33 163.6(6) . . . . ?
C26 P1 C23 C22 -78.7(5) . . . . ?
C26 P1 C23 C24 106.5(6) . . . . ?
C26 C27 C28 C29 -1.0(11) . . . . ?
C9 C8 N1 C19 -55.6(10) . . . . ?
C9 C8 N1 C5 119.2(8) . . . . ?
C9 C8 C13 C12 -2.1(13) . . . . ?
C9 C8 P2 C19 18.1(9) . . . . ?
C9 C8 P2 C5 106.7(8) . . . . ?
C27 C26 C31 C30 0.5(10) . . . . ?
C27 C26 N2 C32 126.2(11) . . . . ?
C27 C26 N2 C23 -69.8(12) . . . . ?
C27 C28 C29 C30 -0.7(12) . . . . ?
C19 C18 C17 C16 2.3(19) . . . . ?
C19 N1 C5 C6 -33.8(12) . . . . ?
C19 N1 C5 C4 139.1(7) . . . . ?
C19 C14 C15 C16 0.8(15) . . . . ?
C19 C18A C17A C16A -3(5) . . . . ?
C24 C23 N2 C26 141.9(10) . . . . ?
C24 C23 N2 C32 -56.4(18) . . . . ?
C6 C7 C2 C1 -173.9(5) . . . . ?
C6 C7 C2 C3 0.7(8) . . . . ?
C6 C5 C4 C3 0.7(11) . . . . ?
C37 C32 C33 C34 -4.3(12) . . . . ?
C37 C32 N2 C26 -72.2(13) . . . . ?
C37 C32 N2 C23 126.5(15) . . . . ?
C32 P1 C26 C27 83.8(6) . . . . ?
C32 P1 C26 C31 -104.9(6) . . . . ?
C32 P1 C23 C22 179.2(5) . . . . ?
C32 P1 C23 C24 4.4(7) . . . . ?
C32 C37 C36 C35 -0.4(13) . . . . ?
C23 P1 C26 C27 -14.2(7) . . . . ?
C23 P1 C26 C31 157.1(6) . . . . ?
C23 P1 C32 C37 88.8(7) . . . . ?
C23 P1 C32 C33 -96.8(6) . . . . ?
C11 C12 C13 C8 -0.3(13) . . . . ?
C8 C9 C10 C11 -0.3(13) . . . . ?
C8 N1 C5 C6 151.5(7) . . . . ?
C8 N1 C5 C4 -35.6(11) . . . . ?
C12 C11 C10 C9 -2.1(13) . . . . ?
C18 C19 N1 C8 127.6(10) . . . . ?
C18 C19 N1 C5 -47.4(12) . . . . ?
C18 C19 C14 C15 3.3(15) . . . . ?
N1 C19 C18 C17 -177.5(8) . . . . ?
N1 C19 C14 C15 176.2(8) . . . . ?
N1 C8 C13 C12 167.1(8) . . . . ?
N1 C5 C4 C3 -172.8(7) . . . . ?
C34 C35 C36 C37 0.0(13) . . . . ?
C35 C34 C33 C32 4.0(13) . . . . ?
C13 C8 N1 C19 134.9(8) . . . . ?
C13 C8 N1 C5 -50.3(12) . . . . ?
C13 C8 P2 C19 173.8(6) . . . . ?
C13 C8 P2 C5 -97.7(6) . . . . ?
C33 C32 N2 C26 132.7(10) . . . . ?
C33 C32 N2 C23 -29(3) . . . . ?
C33 C34 C35 C36 -1.8(12) . . . . ?
C10 C9 C8 N1 -167.6(7) . . . . ?
C10 C9 C8 C13 2.3(12) . . . . ?
C10 C9 C8 P2 154.9(7) . . . . ?
C10 C11 C12 C13 2.3(12) . . . . ?
C31 C26 C27 C28 1.0(10) . . . . ?
C31 C26 N2 C32 -36(2) . . . . ?
C31 C26 N2 C23 128.2(12) . . . . ?
C31 C30 C29 C28 2.2(13) . . . . ?
C36 C37 C32 P1 176.6(6) . . . . ?
C36 C37 C32 C33 2.5(12) . . . . ?
C36 C37 C32 N2 -157.7(10) . . . . ?
C29 C30 C31 C26 -2.1(12) . . . . ?
C14 C19 C18 C17 -4.7(17) . . . . ?
C14 C19 N1 C8 -46.3(9) . . . . ?
C14 C19 N1 C5 138.8(8) . . . . ?
C17 C16 C15 C14 -2.6(17) . . . . ?
C15 C16 C17 C18 1.0(19) . . . . ?
P2 C19 C18A C17A 163(2) . . . . ?
P2 C19 C14A C15A -177(2) . . . . ?
P2 C8 C13 C12 -162.1(7) . . . . ?
P2 C5 C4 C3 157.8(7) . . . . ?
N2 C26 C27 C28 -168.3(8) . . . . ?
N2 C26 C31 C30 161.1(13) . . . . ?
N2 C32 C33 C34 148.2(13) . . . . ?
C18A C19 P2 C8 86(2) . . . . ?
C18A C19 P2 C5 5(2) . . . . ?
C18A C19 C14A C15A -16(3) . . . . ?
C18A C17A C16A C15A 3(4) . . . . ?
C17A C16A C15A C14A -9(4) . . . . ?
C16A C15A C14A C19 18(4) . . . . ?
C14A C19 P2 C8 -121.9(11) . . . . ?
C14A C19 P2 C5 157.3(11) . . . . ?
C14A C19 C18A C17A 7(4) . . . . ?

_olex2_date_sample_data_collection 2017-07-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_17070701
_database_code_depnum_ccdc_archive 'CCDC 1587617'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ONdP(GC)
_chemical_formula_moiety         'C37 H28 N O P'
_chemical_formula_sum            'C37 H28 N O P'
_chemical_formula_weight         533.57
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOP
_chemical_oxdiff_usercomment     ONdP-nH
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           9
_space_group_name_H-M_alt        Cc
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   23.584(4)
_cell_length_b                   6.0025(7)
_cell_length_c                   21.526(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.573(14)
_cell_angle_gamma                90
_cell_volume                     2974.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3564
_cell_measurement_temperature    272(4)
_cell_measurement_theta_max      73.7840
_cell_measurement_theta_min      3.7830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4795
_diffrn_reflns_point_group_measured_fraction_full 0.633
_diffrn_reflns_point_group_measured_fraction_max 0.599
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.913
_diffrn_reflns_theta_min         3.841
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      272(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  28.00   1.00    1.78    --  -40.50  57.00  30.00   95
  2  ω    -93.00  -2.00   1.00    1.78    --  -40.50 125.00 120.00   91
  3  ω     27.00  53.00   1.00    1.78    --   42.99-125.00 -60.00   26
  4  ω     36.00 130.00   1.00    7.14    --  107.32 -45.00-180.00   94
  5  ω    109.00 178.00   1.00    7.14    --  107.32  45.00-120.00   69
  6  ω     92.00 178.00   1.00    7.14    --  107.32  61.00 -30.00   86
  7  ω     26.00  91.00   1.00    7.14    --  107.32 -94.00  90.00   65
  8  ω     30.00  62.00   1.00    7.14    --  107.32 -94.00  30.00   32
  9  ω     21.00  47.00   1.00    1.78    --   42.99  37.00 -30.00   26
 10  ω     91.00 116.00   1.00    1.78    --   42.99  37.00 -30.00   25
 11  ω    131.00 142.00   1.00    7.14    --  107.32 125.00  90.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0500142000
_diffrn_orient_matrix_UB_12      0.1043502000
_diffrn_orient_matrix_UB_13      -0.0257590000
_diffrn_orient_matrix_UB_21      -0.0431452000
_diffrn_orient_matrix_UB_22      0.1625604000
_diffrn_orient_matrix_UB_23      -0.0410888000
_diffrn_orient_matrix_UB_31      0.0105934000
_diffrn_orient_matrix_UB_32      0.1690647000
_diffrn_orient_matrix_UB_33      0.0550551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.266
_reflns_Friedel_fraction_full    0.280
_reflns_Friedel_fraction_max     0.252
_reflns_number_gt                3278
_reflns_number_total             3619
_reflns_odcompleteness_completeness 98.74
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.612
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.372
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0872
_refine_ls_restrained_S_all      1.371
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2447
_refine_ls_wR_factor_ref         0.2916
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-C1 \\sim O1A-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C7(H7), C24(H24), C4(H4), C13(H13), C6(H6), C34(H34), C27(H27),
 C21(H21), C3(H3), C22(H22), C35(H35), C36(H36), C33(H33), C19(H19), C18(H18),
 C12(H12), C31(H31), C29(H29), C17(H17), C30(H30), C16(H16), C9(H9), C11(H11),
 C15(H15), C10(H10), C28(H28), C37(H37)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
P1 P 0.62588(8) 0.6531(3) 0.33593(8) 0.0564(5) Uani 1 1 d . . . . .
C20 C 0.4593(3) 0.2284(10) 0.5437(3) 0.0436(12) Uani 1 1 d . . . . .
O1 O 0.4848(12) -0.0887(19) 0.4916(11) 0.074(5) Uani 0.56(3) 1 d D . P A 1
C25 C 0.4317(3) 0.4314(11) 0.5303(3) 0.0451(13) Uani 1 1 d . . . . .
H25 H 0.4370 0.5135 0.4953 0.054 Uiso 1 1 calc R . . . .
C2 C 0.5220(3) 0.2494(10) 0.4602(3) 0.0460(13) Uani 1 1 d . . . . .
C7 C 0.5470(3) 0.4611(11) 0.4775(3) 0.0461(13) Uani 1 1 d . . . . .
H7 H 0.5426 0.5257 0.5155 0.055 Uiso 1 1 calc R . . . .
C24 C 0.3962(3) 0.5137(11) 0.5687(3) 0.0492(14) Uani 1 1 d . . . . .
H24 H 0.3770 0.6483 0.5584 0.059 Uiso 1 1 calc R . . . .
C4 C 0.5610(3) 0.2699(12) 0.3646(3) 0.0553(15) Uani 1 1 d . . . . .
H4 H 0.5658 0.2054 0.3267 0.066 Uiso 1 1 calc R . . . .
C23 C 0.3890(3) 0.3971(14) 0.6228(3) 0.0526(15) Uani 1 1 d . . . . .
C8 C 0.6206(3) 0.4780(13) 0.2667(3) 0.0515(15) Uani 1 1 d . . . . .
C1 C 0.4925(4) 0.1172(11) 0.5013(4) 0.0556(16) Uani 1 1 d D . . . .
C13 C 0.6571(3) 0.2999(17) 0.2594(4) 0.065(2) Uani 1 1 d . . . . .
H13 H 0.6883 0.2653 0.2925 0.078 Uiso 1 1 calc R . . . .
C26 C 0.2958(3) 0.5586(13) 0.6316(4) 0.0546(15) Uani 1 1 d . . . . .
C5 C 0.5858(3) 0.4813(12) 0.3825(3) 0.0495(14) Uani 1 1 d . . . . .
C6 C 0.5776(3) 0.5737(11) 0.4397(3) 0.0468(13) Uani 1 1 d . . . . .
H6 H 0.5930 0.7132 0.4523 0.056 Uiso 1 1 calc R . . . .
N1 N 0.3519(3) 0.4755(14) 0.6608(3) 0.0623(17) Uani 1 1 d . . . . .
C34 C 0.4249(4) 0.3782(18) 0.8300(4) 0.075(2) Uani 1 1 d . . . . .
H34 H 0.4603 0.4100 0.8573 0.091 Uiso 1 1 calc R . . . .
C27 C 0.2618(3) 0.4468(17) 0.5809(4) 0.068(2) Uani 1 1 d . . . . .
H27 H 0.2748 0.3174 0.5647 0.082 Uiso 1 1 calc R . . . .
C21 C 0.4523(3) 0.1126(11) 0.5984(3) 0.0529(15) Uani 1 1 d . . . . .
H21 H 0.4709 -0.0235 0.6081 0.064 Uiso 1 1 calc R . . . .
C14 C 0.6997(3) 0.6077(13) 0.3804(4) 0.0553(15) Uani 1 1 d . . . . .
C3 C 0.5296(4) 0.1565(11) 0.4025(4) 0.0581(17) Uani 1 1 d . . . . .
H3 H 0.5135 0.0181 0.3895 0.070 Uiso 1 1 calc R . . . .
C32 C 0.3620(3) 0.4076(13) 0.7273(3) 0.0542(15) Uani 1 1 d . . . . .
C22 C 0.4189(3) 0.1936(13) 0.6375(3) 0.0563(16) Uani 1 1 d . . . . .
H22 H 0.4158 0.1150 0.6738 0.068 Uiso 1 1 calc R . . . .
C35 C 0.3839(4) 0.260(2) 0.8516(4) 0.085(3) Uani 1 1 d . . . . .
H35 H 0.3916 0.2061 0.8931 0.102 Uiso 1 1 calc R . . . .
C36 C 0.3307(4) 0.222(2) 0.8114(4) 0.082(3) Uani 1 1 d . . . . .
H36 H 0.3019 0.1465 0.8264 0.098 Uiso 1 1 calc R . . . .
C33 C 0.4144(4) 0.4508(19) 0.7678(4) 0.075(2) Uani 1 1 d . . . . .
H33 H 0.4429 0.5293 0.7532 0.090 Uiso 1 1 calc R . . . .
C19 C 0.7168(3) 0.4361(18) 0.4241(4) 0.068(2) Uani 1 1 d . . . . .
H19 H 0.6896 0.3299 0.4295 0.081 Uiso 1 1 calc R . . . .
C18 C 0.7727(4) 0.419(2) 0.4595(4) 0.082(3) Uani 1 1 d . . . . .
H18 H 0.7828 0.2994 0.4873 0.098 Uiso 1 1 calc R . . . .
C12 C 0.6478(4) 0.1741(19) 0.2040(5) 0.079(3) Uani 1 1 d . . . . .
H12 H 0.6728 0.0574 0.2001 0.095 Uiso 1 1 calc R . . . .
C31 C 0.2744(5) 0.7435(18) 0.6584(7) 0.089(3) Uani 1 1 d . . . . .
H31 H 0.2963 0.8092 0.6949 0.106 Uiso 1 1 calc R . . . .
C29 C 0.1867(6) 0.729(3) 0.5808(8) 0.120(6) Uani 1 1 d . . . . .
H29 H 0.1501 0.7883 0.5640 0.144 Uiso 1 1 calc R . . . .
C17 C 0.8129(4) 0.5726(19) 0.4543(5) 0.081(3) Uani 1 1 d . . . . .
H17 H 0.8507 0.5588 0.4780 0.098 Uiso 1 1 calc R . . . .
C30 C 0.2227(6) 0.825(2) 0.6315(9) 0.108(4) Uani 1 1 d . . . . .
H30 H 0.2104 0.9546 0.6483 0.129 Uiso 1 1 calc R . . . .
C16 C 0.7982(5) 0.746(2) 0.4146(6) 0.092(3) Uani 1 1 d . . . . .
H16 H 0.8256 0.8544 0.4115 0.111 Uiso 1 1 calc R . . . .
C9 C 0.5745(4) 0.5270(19) 0.2155(4) 0.077(3) Uani 1 1 d . . . . .
H9 H 0.5503 0.6477 0.2179 0.093 Uiso 1 1 calc R . . . .
C11 C 0.6013(5) 0.223(2) 0.1548(4) 0.085(3) Uani 1 1 d . . . . .
H11 H 0.5948 0.1402 0.1174 0.102 Uiso 1 1 calc R . . . .
C15 C 0.7426(5) 0.7640(17) 0.3788(6) 0.083(3) Uani 1 1 d . . . . .
H15 H 0.7333 0.8867 0.3521 0.100 Uiso 1 1 calc R . . . .
C10 C 0.5648(4) 0.395(2) 0.1612(5) 0.091(3) Uani 1 1 d . . . . .
H10 H 0.5328 0.4243 0.1284 0.109 Uiso 1 1 calc R . . . .
C28 C 0.2063(5) 0.537(4) 0.5543(6) 0.121(6) Uani 1 1 d . . . . .
H28 H 0.1826 0.4686 0.5192 0.145 Uiso 1 1 calc R . . . .
C37 C 0.3200(3) 0.2937(17) 0.7491(4) 0.067(2) Uani 1 1 d . . . . .
H37 H 0.2844 0.2649 0.7220 0.081 Uiso 1 1 calc R . . . .
O1A O 0.5097(16) -0.080(3) 0.5113(15) 0.074(5) Uani 0.44(3) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C8 1.806(7) . ?
P1 C5 1.837(7) . ?
P1 C14 1.816(8) . ?
C20 C25 1.382(9) . ?
C20 C1 1.484(9) . ?
C20 C21 1.408(9) . ?
O1 C1 1.260(14) . ?
C25 H25 0.9300 . ?
C25 C24 1.390(10) . ?
C2 C7 1.416(9) . ?
C2 C1 1.472(10) . ?
C2 C3 1.408(9) . ?
C7 H7 0.9300 . ?
C7 C6 1.376(10) . ?
C24 H24 0.9300 . ?
C24 C23 1.399(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.415(10) . ?
C4 C3 1.393(10) . ?
C23 N1 1.404(9) . ?
C23 C22 1.412(10) . ?
C8 C13 1.404(12) . ?
C8 C9 1.400(9) . ?
C1 O1A 1.257(16) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(12) . ?
C26 N1 1.424(9) . ?
C26 C27 1.380(11) . ?
C26 C31 1.396(13) . ?
C5 C6 1.403(9) . ?
C6 H6 0.9300 . ?
N1 C32 1.457(9) . ?
C34 H34 0.9300 . ?
C34 C35 1.361(16) . ?
C34 C33 1.379(13) . ?
C27 H27 0.9300 . ?
C27 C28 1.417(15) . ?
C21 H21 0.9300 . ?
C21 C22 1.360(10) . ?
C14 C19 1.394(12) . ?
C14 C15 1.385(13) . ?
C3 H3 0.9300 . ?
C32 C33 1.372(11) . ?
C32 C37 1.368(12) . ?
C22 H22 0.9300 . ?
C35 H35 0.9300 . ?
C35 C36 1.380(13) . ?
C36 H36 0.9300 . ?
C36 C37 1.379(12) . ?
C33 H33 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.375(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.346(15) . ?
C12 H12 0.9300 . ?
C12 C11 1.382(14) . ?
C31 H31 0.9300 . ?
C31 C30 1.324(18) . ?
C29 H29 0.9300 . ?
C29 C30 1.36(3) . ?
C29 C28 1.41(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.344(17) . ?
C30 H30 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.374(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(16) . ?
C11 H11 0.9300 . ?
C11 C10 1.369(19) . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C28 H28 0.9300 . ?
C37 H37 0.9300 . ?

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
C8 P1 C5 99.9(3) . . ?
C8 P1 C14 103.6(3) . . ?
C14 P1 C5 100.2(3) . . ?
C25 C20 C1 123.8(6) . . ?
C25 C20 C21 118.3(6) . . ?
C21 C20 C1 117.8(6) . . ?
C20 C25 H25 119.8 . . ?
C20 C25 C24 120.4(6) . . ?
C24 C25 H25 119.8 . . ?
C7 C2 C1 123.3(6) . . ?
C3 C2 C7 117.6(6) . . ?
C3 C2 C1 119.0(6) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.8(6) . . ?
C6 C7 H7 119.1 . . ?
C25 C24 H24 119.5 . . ?
C25 C24 C23 121.0(6) . . ?
C23 C24 H24 119.5 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(6) . . ?
C24 C23 N1 121.4(7) . . ?
C24 C23 C22 118.3(6) . . ?
N1 C23 C22 120.3(7) . . ?
C13 C8 P1 127.0(5) . . ?
C9 C8 P1 115.4(6) . . ?
C9 C8 C13 117.5(8) . . ?
O1 C1 C20 117.7(13) . . ?
O1 C1 C2 120.0(13) . . ?
C2 C1 C20 120.6(6) . . ?
O1A C1 C20 120.9(17) . . ?
O1A C1 C2 115.8(17) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.7(7) . . ?
C12 C13 H13 119.2 . . ?
C27 C26 N1 120.2(7) . . ?
C27 C26 C31 120.8(9) . . ?
C31 C26 N1 118.7(8) . . ?
C4 C5 P1 125.9(5) . . ?
C6 C5 P1 116.3(5) . . ?
C6 C5 C4 117.8(6) . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C23 N1 C26 119.7(6) . . ?
C23 N1 C32 119.3(6) . . ?
C26 N1 C32 118.1(6) . . ?
C35 C34 H34 119.8 . . ?
C35 C34 C33 120.4(7) . . ?
C33 C34 H34 119.8 . . ?
C26 C27 H27 121.2 . . ?
C26 C27 C28 117.5(11) . . ?
C28 C27 H27 121.2 . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 122.0(6) . . ?
C22 C21 H21 119.0 . . ?
C19 C14 P1 124.8(6) . . ?
C15 C14 P1 120.4(7) . . ?
C15 C14 C19 114.3(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C33 C32 N1 120.2(8) . . ?
C37 C32 N1 120.0(6) . . ?
C37 C32 C33 119.7(7) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 119.9(6) . . ?
C21 C22 H22 120.0 . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.3(8) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 H36 119.8 . . ?
C37 C36 C35 120.4(9) . . ?
C37 C36 H36 119.8 . . ?
C34 C33 H33 119.9 . . ?
C32 C33 C34 120.3(9) . . ?
C32 C33 H33 119.9 . . ?
C14 C19 H19 118.9 . . ?
C18 C19 C14 122.1(9) . . ?
C18 C19 H19 118.9 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.6(11) . . ?
C17 C18 H18 119.7 . . ?
C13 C12 H12 120.2 . . ?
C11 C12 C13 119.5(10) . . ?
C11 C12 H12 120.2 . . ?
C26 C31 H31 120.1 . . ?
C30 C31 C26 119.7(13) . . ?
C30 C31 H31 120.1 . . ?
C30 C29 H29 121.0 . . ?
C30 C29 C28 118.1(10) . . ?
C28 C29 H29 121.0 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(9) . . ?
C16 C17 H17 120.1 . . ?
C31 C30 C29 123.3(13) . . ?
C31 C30 H30 118.3 . . ?
C29 C30 H30 118.3 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(9) . . ?
C15 C16 H16 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(9) . . ?
C10 C9 H9 120.0 . . ?
C12 C11 H11 120.1 . . ?
C10 C11 C12 119.7(9) . . ?
C10 C11 H11 120.1 . . ?
C14 C15 H15 118.4 . . ?
C16 C15 C14 123.1(10) . . ?
C16 C15 H15 118.4 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.5(8) . . ?
C11 C10 H10 119.3 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(13) . . ?
C29 C28 H28 119.9 . . ?
C32 C37 C36 119.9(7) . . ?
C32 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.897
_oxdiff_exptl_absorpt_empirical_full_min 0.471
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/n-hexane'
_exptl_crystal_preparation       Luminescent
