# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_zhuyy_0316
_audit_block_doi                 10.5517/ccdc.csd.cc27mnn6
_database_code_depnum_ccdc_archive 'CCDC 2074478'
loop_
_audit_author_name
_audit_author_address
ZHUYY
;lan zhou university
China
;
_audit_update_record             
;
2021-03-31 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-03-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N O3 P'
_chemical_formula_sum            'C21 H18 N O3 P'
_chemical_formula_weight         363.33
_chemical_melting_point          ?
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                   9.52643(9)
_cell_length_b                   14.88162(13)
_cell_length_c                   12.71774(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.7242(8)
_cell_angle_gamma                90
_cell_volume                     1802.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9326
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.0460
_cell_measurement_theta_min      3.4590
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11200
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.049
_diffrn_reflns_theta_min         5.514
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  32.00   0.50    0.05    --  -43.30  48.00 -16.00   80
  2  ω    -50.00 -25.00   0.50    0.05    -- -100.00  45.00  90.00   50
  3  ω    -53.00 -27.00   0.50    0.05    -- -100.00  45.00 150.00   52
  4  ω    -53.00 -24.00   0.50    0.05    -- -100.00  45.00 120.00   58
  5  ω    -68.00 -40.00   0.50    0.05    -- -100.00  61.00 120.00   56
  6  ω    -53.00 -26.00   0.50    0.05    --  -43.30  48.00 -16.00   54
  7  ω    -57.00 -25.00   0.50    0.05    -- -100.00  48.00 -16.00   64
  8  ω    -53.00 -24.00   0.50    0.05    -- -100.00  45.00 -90.00   58
  9  ω    -54.00 -26.00   0.50    0.05    -- -100.00  45.00-180.00   56
 10  ω    -58.00 -27.00   0.50    0.05    -- -100.00  61.00-180.00   62
 11  ω   -117.00 -21.00   0.50    0.05    --  -43.30 -48.00-164.00  192
 12  ω    -35.00  22.00   0.50    0.05    --   43.30 -19.00  60.00  114
 13  ω     45.00  70.00   0.50    0.05    --   43.30  48.00 -16.00   50
 14  ω    132.00 174.00   0.50    0.05    --  109.88  48.00 -16.00   84
 15  ω    142.00 175.00   0.50    0.05    --  109.88  30.00 -90.00   66
 16  ω    102.00 128.00   0.50    0.05    --  109.88  48.00 -16.00   52
 17  ω     86.00 127.00   0.50    0.05    --  109.88  30.00 -90.00   82
 18  ω     92.00 154.00   0.50    0.05    --  109.88  61.00  60.00  124
 19  ω     66.00  92.00   0.50    0.05    --  109.88 -77.00  30.00   52
 20  ω     53.00 105.00   0.50    0.05    --  109.88-125.00 -30.00  104
 21  ω     41.00  95.00   0.50    0.05    --  109.88 -77.00   0.00  108
 22  ω     37.00  67.00   0.50    0.05    --  109.88 -61.00-120.00   60
 23  ω     37.00  63.00   0.50    0.05    --  109.88 -61.00-180.00   52
 24  ω      8.00  33.00   0.50    0.05    --   43.30 -48.00-164.00   50
 25  ω     37.00  66.00   0.50    0.05    --  109.88 -61.00 -30.00   58
 26  ω     40.00  90.00   0.50    0.05    --  109.88 -77.00 150.00  100
 27  ω    -76.00 -48.00   0.50    0.05    --  -43.30-179.00 -30.00   56
 28  ω   -175.00 -89.00   0.50    0.05    -- -100.00 -48.00-164.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1522241000
_diffrn_orient_matrix_UB_12      -0.0009619000
_diffrn_orient_matrix_UB_13      -0.0424639000
_diffrn_orient_matrix_UB_21      0.0448325000
_diffrn_orient_matrix_UB_22      -0.0615694000
_diffrn_orient_matrix_UB_23      -0.0909490000
_diffrn_orient_matrix_UB_31      -0.0314488000
_diffrn_orient_matrix_UB_32      -0.0832020000
_diffrn_orient_matrix_UB_33      0.0677923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3317
_reflns_number_total             3586
_reflns_odcompleteness_completeness 99.55
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.025
_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)+(0.0694P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
P1 P 0.25727(3) 0.68431(2) 0.97730(2) 0.03919(13) Uani 1 1 d . . . . .
O1 O 0.33035(10) 0.59075(7) 1.00293(9) 0.0513(3) Uani 1 1 d . . . . .
O2 O -0.02339(11) 0.62754(7) 1.17977(9) 0.0590(3) Uani 1 1 d . . . . .
O3 O 0.19990(10) 0.69386(7) 0.87102(8) 0.0495(2) Uani 1 1 d . . . . .
N1 N 0.13714(12) 0.69105(7) 1.07248(9) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.25710(13) 0.51664(9) 1.04034(11) 0.0423(3) Uani 1 1 d . . . . .
C2 C 0.13690(13) 0.52834(9) 1.09925(10) 0.0405(3) Uani 1 1 d . . . . .
C3 C 0.07073(15) 0.45109(10) 1.13671(11) 0.0483(3) Uani 1 1 d . . . . .
H3 H -0.010219 0.456511 1.176330 0.058 Uiso 1 1 calc R U . . .
C4 C 0.12387(16) 0.36716(10) 1.11569(13) 0.0543(4) Uani 1 1 d . . . . .
H4 H 0.078373 0.316302 1.140655 0.065 Uiso 1 1 calc R U . . .
C5 C 0.24465(16) 0.35814(10) 1.05758(13) 0.0548(4) Uani 1 1 d . . . . .
H5 H 0.280670 0.301230 1.044349 0.066 Uiso 1 1 calc R U . . .
C6 C 0.31227(15) 0.43319(10) 1.01901(13) 0.0513(3) Uani 1 1 d . . . . .
H6 H 0.393266 0.427434 0.979504 0.062 Uiso 1 1 calc R U . . .
C7 C 0.07631(14) 0.61767(9) 1.12201(10) 0.0426(3) Uani 1 1 d . . . . .
C8 C 0.06791(15) 0.77955(9) 1.08517(11) 0.0446(3) Uani 1 1 d . . . . .
H8A H -0.033073 0.771244 1.082796 0.054 Uiso 1 1 calc R U . . .
H8B H 0.093038 0.817969 1.026737 0.054 Uiso 1 1 calc R U . . .
C9 C 0.10847(18) 0.82606(10) 1.18764(12) 0.0538(4) Uani 1 1 d . . . . .
H9A H 0.071669 0.792193 1.246347 0.065 Uiso 1 1 calc R U . . .
H9B H 0.209937 0.827569 1.194772 0.065 Uiso 1 1 calc R U . . .
C10 C 0.05184(15) 0.92057(9) 1.19062(11) 0.0454(3) Uani 1 1 d . . . . .
C11 C -0.07984(17) 0.93908(11) 1.22872(12) 0.0570(4) Uani 1 1 d . . . . .
H11 H -0.134466 0.892760 1.255318 0.068 Uiso 1 1 calc R U . . .
C12 C -0.13172(19) 1.02642(14) 1.22773(14) 0.0692(5) Uani 1 1 d . . . . .
H12 H -0.220549 1.038217 1.253923 0.083 Uiso 1 1 calc R U . . .
C13 C -0.0525(2) 1.09513(12) 1.18835(15) 0.0705(5) Uani 1 1 d . . . . .
H13 H -0.087395 1.153499 1.187385 0.085 Uiso 1 1 calc R U . . .
C14 C 0.0773(2) 1.07738(13) 1.15072(19) 0.0828(6) Uani 1 1 d . . . . .
H14 H 0.131221 1.123865 1.123726 0.099 Uiso 1 1 calc R U . . .
C15 C 0.12979(19) 0.99123(12) 1.15215(17) 0.0692(5) Uani 1 1 d . . . . .
H15 H 0.219348 0.980427 1.126760 0.083 Uiso 1 1 calc R U . . .
C16 C 0.39365(13) 0.76264(9) 1.00557(10) 0.0410(3) Uani 1 1 d . . . . .
C17 C 0.46705(15) 0.76099(11) 1.10090(11) 0.0520(3) Uani 1 1 d . . . . .
H17 H 0.443799 0.719091 1.152069 0.062 Uiso 1 1 calc R U . . .
C18 C 0.57447(18) 0.82161(12) 1.11955(14) 0.0614(4) Uani 1 1 d . . . . .
H18 H 0.623610 0.820598 1.183195 0.074 Uiso 1 1 calc R U . . .
C19 C 0.60841(18) 0.88352(12) 1.04346(15) 0.0635(4) Uani 1 1 d . . . . .
H19 H 0.680298 0.924535 1.056178 0.076 Uiso 1 1 calc R U . . .
C20 C 0.53708(18) 0.88520(11) 0.94904(14) 0.0618(4) Uani 1 1 d . . . . .
H20 H 0.561371 0.927039 0.898089 0.074 Uiso 1 1 calc R U . . .
C21 C 0.42904(16) 0.82492(10) 0.92918(12) 0.0489(3) Uani 1 1 d . . . . .
H21 H 0.380702 0.826218 0.865205 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.5887(10) . ?
P1 O3 1.4584(10) . ?
P1 N1 1.6794(11) . ?
P1 C16 1.7788(13) . ?
O1 C1 1.3921(16) . ?
O2 C7 1.2170(16) . ?
N1 C7 1.3908(17) . ?
N1 C8 1.4826(16) . ?
C1 C2 1.3873(18) . ?
C1 C6 1.3768(19) . ?
C2 C3 1.3977(19) . ?
C2 C7 1.4794(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5212(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.507(2) . ?
C10 C11 1.378(2) . ?
C10 C15 1.380(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.3921(19) . ?
C16 C21 1.3875(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(2) . ?
C21 H21 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
O1 P1 N1 101.85(5) . . ?
O1 P1 C16 102.46(6) . . ?
O3 P1 O1 115.70(6) . . ?
O3 P1 N1 114.29(6) . . ?
O3 P1 C16 112.81(6) . . ?
N1 P1 C16 108.53(6) . . ?
C1 O1 P1 122.97(8) . . ?
C7 N1 P1 124.83(9) . . ?
C7 N1 C8 117.37(11) . . ?
C8 N1 P1 116.08(9) . . ?
C2 C1 O1 120.39(12) . . ?
C6 C1 O1 116.94(12) . . ?
C6 C1 C2 122.64(12) . . ?
C1 C2 C3 117.37(12) . . ?
C1 C2 C7 123.04(12) . . ?
C3 C2 C7 119.58(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.80(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.21(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.42(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.56(14) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O2 C7 N1 120.76(13) . . ?
O2 C7 C2 122.41(12) . . ?
N1 C7 C2 116.82(11) . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
N1 C8 C9 112.88(11) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.04(12) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C11 C10 C9 121.54(14) . . ?
C11 C10 C15 117.93(15) . . ?
C15 C10 C9 120.51(14) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.58(16) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.25(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.49(17) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.61(18) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.15(17) . . ?
C14 C15 H15 119.4 . . ?
C17 C16 P1 121.47(10) . . ?
C21 C16 P1 118.66(11) . . ?
C21 C16 C17 119.85(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.03(14) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.72(15) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.58(15) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.40(15) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 120.3 . . ?
C20 C21 C16 119.42(14) . . ?
C20 C21 H21 120.3 . . ?

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 O1 C1 C2 -28.33(18) . . . . ?
P1 O1 C1 C6 153.77(11) . . . . ?
P1 N1 C7 O2 -169.89(11) . . . . ?
P1 N1 C7 C2 8.98(17) . . . . ?
P1 N1 C8 C9 -111.68(12) . . . . ?
P1 C16 C17 C18 178.64(13) . . . . ?
P1 C16 C21 C20 -178.63(13) . . . . ?
O1 P1 N1 C7 -27.22(12) . . . . ?
O1 P1 N1 C8 168.15(9) . . . . ?
O1 P1 C16 C17 -51.30(13) . . . . ?
O1 P1 C16 C21 127.03(12) . . . . ?
O1 C1 C2 C3 -178.30(12) . . . . ?
O1 C1 C2 C7 2.6(2) . . . . ?
O1 C1 C6 C5 178.11(13) . . . . ?
O3 P1 O1 C1 -88.05(12) . . . . ?
O3 P1 N1 C7 98.29(12) . . . . ?
O3 P1 N1 C8 -66.34(11) . . . . ?
O3 P1 C16 C17 -176.38(11) . . . . ?
O3 P1 C16 C21 1.95(14) . . . . ?
N1 P1 O1 C1 36.53(12) . . . . ?
N1 P1 C16 C17 55.91(13) . . . . ?
N1 P1 C16 C21 -125.76(11) . . . . ?
N1 C8 C9 C10 172.24(12) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C2 C7 O2 -174.77(13) . . . . ?
C1 C2 C7 N1 6.38(19) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C2 C7 O2 6.2(2) . . . . ?
C3 C2 C7 N1 -172.66(12) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 C1 C2 C7 -179.59(13) . . . . ?
C7 N1 C8 C9 82.50(15) . . . . ?
C7 C2 C3 C4 179.25(13) . . . . ?
C8 N1 C7 O2 -5.44(19) . . . . ?
C8 N1 C7 C2 173.43(11) . . . . ?
C8 C9 C10 C11 88.70(17) . . . . ?
C8 C9 C10 C15 -89.48(19) . . . . ?
C9 C10 C11 C12 -178.00(15) . . . . ?
C9 C10 C15 C14 177.53(18) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C15 C10 C11 C12 0.2(2) . . . . ?
C16 P1 O1 C1 148.79(11) . . . . ?
C16 P1 N1 C7 -134.85(11) . . . . ?
C16 P1 N1 C8 60.53(11) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C16 C21 C20 -0.3(2) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C21 C16 C17 C18 0.3(2) . . . . ?

_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 11.535
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_zhuyy-1_0414_pl
_database_code_depnum_ccdc_archive 'CCDC 2015301'
_audit_update_record             
;
2020-07-09 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-04-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 N O2 P'
_chemical_formula_sum            'C26 H22 N O2 P'
_chemical_formula_weight         411.41
_chemical_melting_point          ?
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                   15.6285(3)
_cell_length_b                   9.3057(2)
_cell_length_c                   14.6152(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.164(2)
_cell_angle_gamma                90
_cell_volume                     2116.92(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8670
_cell_measurement_theta_min      5.5310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7576
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         5.539
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  68.00   1.00    1.00    --    0.00  57.00  30.00   31
  2  ω     31.00 123.00   1.00    1.00    --   54.00  38.00 120.00   92
  3  ω    108.00 133.00   1.00    5.00    --  108.00 -38.00   0.00   25
  4  ω    109.00 168.00   1.00    5.00    --  108.00 -12.00 -60.00   59
  5  ω     80.00 125.00   1.00    5.00    --  108.00 -50.00-180.00   45
  6  ω     49.00 115.00   1.00    5.00    --  108.00 -91.00 -60.00   66
  7  ω     61.00  87.00   1.00    1.00    --   54.00-125.00   0.00   26
  8  ω     41.00 129.00   1.00    5.00    --  108.00 -63.00   0.00   88
  9  ω     59.00  84.00   1.00    5.00    --  108.00 -38.00   0.00   25
 10  ω     37.00  90.00   1.00    5.00    --  108.00 -12.00 -60.00   53
 11  ω     37.00  69.00   1.00    1.00    --   54.00  57.00-120.00   32
 12  ω     25.00  63.00   1.00    1.00    --    0.00  57.00 -90.00   38
 13  ω    -13.00  27.00   1.00    1.00    --    0.00  57.00  30.00   40
 14  ω    -18.00  79.00   1.00    1.00    --   54.00 -38.00 -60.00   97
 15  ω     41.00 114.00   1.00    5.00    --  108.00-111.00 -90.00   73
 16  ω     24.00  68.00   1.00    1.00    --   54.00-125.00-150.00   44
 17  ω     41.00 107.00   1.00    5.00    --  108.00 -63.00 120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0269746000
_diffrn_orient_matrix_UB_12      0.1360953000
_diffrn_orient_matrix_UB_13      -0.0501584000
_diffrn_orient_matrix_UB_21      0.0726981000
_diffrn_orient_matrix_UB_22      0.0261067000
_diffrn_orient_matrix_UB_23      0.0765847000
_diffrn_orient_matrix_UB_31      0.0614472000
_diffrn_orient_matrix_UB_32      -0.0905688000
_diffrn_orient_matrix_UB_33      -0.0531997000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3147
_reflns_number_total             3736
_reflns_odcompleteness_completeness 99.90
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.034
_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)+(0.0608P)²+0.2344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
 C30(H30), C31(H31), C38(H38), C40(H40), C42(H42), C46(H46), C50(H50), C51(H51),
  C52(H52), C53(H53), C56(H56), C57(H57), C60(H60)
;
_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
P1 P 0.27396(3) 0.35403(5) 0.16304(3) 0.04062(14) Uani 1 1 d . . . . .
O3 O 0.11773(8) 0.04652(15) 0.10085(11) 0.0581(4) Uani 1 1 d . . . . .
O4 O 0.32073(9) 0.43512(16) 0.09631(10) 0.0583(4) Uani 1 1 d . . . . .
N5 N 0.18730(9) 0.25981(16) 0.11836(10) 0.0407(3) Uani 1 1 d . . . . .
C7 C 0.07739(10) 0.34637(18) -0.00387(12) 0.0412(4) Uani 1 1 d . . . . .
C10 C 0.26304(11) 0.04109(19) 0.06977(11) 0.0418(4) Uani 1 1 d . . . . .
C11 C 0.16834(11) 0.43273(19) 0.30266(12) 0.0442(4) Uani 1 1 d . . . . .
H11 H 0.144727 0.340995 0.298164 0.053 Uiso 1 1 calc R U . . .
C12 C 0.23068(10) 0.47280(17) 0.24514(11) 0.0399(3) Uani 1 1 d . . . . .
C16 C 0.18448(10) 0.11252(19) 0.09928(11) 0.0407(4) Uani 1 1 d . . . . .
C18 C 0.31603(13) 0.1598(2) 0.30718(14) 0.0542(5) Uani 1 1 d . . . . .
H18 H 0.259674 0.169825 0.321921 0.065 Uiso 1 1 calc R U . . .
C21 C 0.34194(11) 0.22858(19) 0.23043(13) 0.0443(4) Uani 1 1 d . . . . .
C22 C 0.14144(12) 0.5286(2) 0.36634(13) 0.0506(4) Uani 1 1 d . . . . .
H22 H 0.099739 0.501198 0.404423 0.061 Uiso 1 1 calc R U . . .
C23 C 0.11942(12) 0.4401(2) -0.05829(14) 0.0512(4) Uani 1 1 d . . . . .
H23 H 0.165997 0.492915 -0.032427 0.061 Uiso 1 1 calc R U . . .
C25 C 0.17612(14) 0.6643(2) 0.37358(14) 0.0575(5) Uani 1 1 d . . . . .
H25 H 0.157835 0.728521 0.416513 0.069 Uiso 1 1 calc R U . . .
C26 C 0.31295(12) 0.1087(2) 0.00905(12) 0.0494(4) Uani 1 1 d . . . . .
H26 H 0.302725 0.204181 -0.007153 0.059 Uiso 1 1 calc R U . . .
C29 C 0.37816(14) 0.0330(3) -0.02739(15) 0.0624(5) Uani 1 1 d . . . . .
H29 H 0.411431 0.077477 -0.068835 0.075 Uiso 1 1 calc R U . . .
C30 C 0.26527(12) 0.6101(2) 0.25326(14) 0.0501(4) Uani 1 1 d . . . . .
H30 H 0.307016 0.638429 0.215466 0.060 Uiso 1 1 calc R U . . .
C31 C 0.27779(13) -0.1022(2) 0.09298(13) 0.0544(5) Uani 1 1 d . . . . .
H31 H 0.243111 -0.148375 0.132293 0.065 Uiso 1 1 calc R U . . .
C38 C 0.00894(11) 0.2679(2) -0.04439(14) 0.0522(4) Uani 1 1 d . . . . .
H38 H -0.019667 0.203313 -0.009317 0.063 Uiso 1 1 calc R U . . .
C40 C 0.34411(16) -0.1757(3) 0.05748(17) 0.0699(6) Uani 1 1 d . . . . .
H40 H 0.355048 -0.270925 0.074031 0.084 Uiso 1 1 calc R U . . .
C42 C 0.37266(17) 0.0766(3) 0.36207(16) 0.0709(6) Uani 1 1 d . . . . .
H42 H 0.354703 0.032211 0.414055 0.085 Uiso 1 1 calc R U . . .
C43 C 0.10369(11) 0.3360(2) 0.09749(12) 0.0474(4) Uani 1 1 d . . . . .
H43A H 0.108267 0.432115 0.123161 0.057 Uiso 1 1 calc R U . . .
H43B H 0.059350 0.285490 0.126989 0.057 Uiso 1 1 calc R U . . .
C46 C 0.09298(14) 0.4561(2) -0.15059(15) 0.0598(5) Uani 1 1 d . . . . .
H46 H 0.121774 0.519504 -0.186263 0.072 Uiso 1 1 calc R U . . .
C50 C 0.23781(14) 0.7052(2) 0.31743(16) 0.0604(5) Uani 1 1 d . . . . .
H50 H 0.261200 0.797024 0.322557 0.073 Uiso 1 1 calc R U . . .
C51 C 0.02452(14) 0.3788(3) -0.18971(14) 0.0613(5) Uani 1 1 d . . . . .
H51 H 0.006625 0.390254 -0.251706 0.074 Uiso 1 1 calc R U . . .
C52 C 0.42540(13) 0.2104(3) 0.20757(19) 0.0708(6) Uani 1 1 d . . . . .
H52 H 0.443748 0.255536 0.156019 0.085 Uiso 1 1 calc R U . . .
C53 C -0.01740(12) 0.2849(3) -0.13736(15) 0.0628(6) Uani 1 1 d . . . . .
H53 H -0.063699 0.232132 -0.163926 0.075 Uiso 1 1 calc R U . . .
C56 C 0.39393(15) -0.1079(3) -0.00240(17) 0.0722(6) Uani 1 1 d . . . . .
H56 H 0.438563 -0.157621 -0.026193 0.087 Uiso 1 1 calc R U . . .
C57 C 0.45558(18) 0.0591(3) 0.3400(2) 0.0911(9) Uani 1 1 d . . . . .
H57 H 0.494066 0.003735 0.377288 0.109 Uiso 1 1 calc R U . . .
C60 C 0.48141(16) 0.1240(4) 0.2626(3) 0.0986(10) Uani 1 1 d . . . . .
H60 H 0.537115 0.109802 0.246794 0.118 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O4 1.4776(13) . ?
P1 N5 1.6942(14) . ?
P1 C12 1.8069(16) . ?
P1 C21 1.8092(18) . ?
O3 C16 1.213(2) . ?
N5 C16 1.399(2) . ?
N5 C43 1.494(2) . ?
C7 C23 1.385(3) . ?
C7 C38 1.384(3) . ?
C7 C43 1.504(2) . ?
C10 C16 1.494(2) . ?
C10 C26 1.384(2) . ?
C10 C31 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(2) . ?
C11 C22 1.382(2) . ?
C12 C30 1.389(2) . ?
C18 H18 0.9300 . ?
C18 C21 1.384(3) . ?
C18 C42 1.378(3) . ?
C21 C52 1.386(3) . ?
C22 H22 0.9300 . ?
C22 C25 1.375(3) . ?
C23 H23 0.9300 . ?
C23 C46 1.383(3) . ?
C25 H25 0.9300 . ?
C25 C50 1.375(3) . ?
C26 H26 0.9300 . ?
C26 C29 1.384(3) . ?
C29 H29 0.9300 . ?
C29 C56 1.378(4) . ?
C30 H30 0.9300 . ?
C30 C50 1.385(3) . ?
C31 H31 0.9300 . ?
C31 C40 1.382(3) . ?
C38 H38 0.9300 . ?
C38 C53 1.393(3) . ?
C40 H40 0.9300 . ?
C40 C56 1.376(4) . ?
C42 H42 0.9300 . ?
C42 C57 1.373(4) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C46 H46 0.9300 . ?
C46 C51 1.371(3) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C51 C53 1.367(3) . ?
C52 H52 0.9300 . ?
C52 C60 1.391(4) . ?
C53 H53 0.9300 . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C57 C60 1.375(5) . ?
C60 H60 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
O4 P1 N5 115.83(8) . . ?
O4 P1 C12 111.28(8) . . ?
O4 P1 C21 112.81(9) . . ?
N5 P1 C12 103.79(7) . . ?
N5 P1 C21 106.60(8) . . ?
C12 P1 C21 105.65(8) . . ?
C16 N5 P1 126.43(12) . . ?
C16 N5 C43 114.40(14) . . ?
C43 N5 P1 119.16(12) . . ?
C23 C7 C43 120.27(16) . . ?
C38 C7 C23 118.35(17) . . ?
C38 C7 C43 121.32(17) . . ?
C26 C10 C16 120.55(16) . . ?
C26 C10 C31 120.10(17) . . ?
C31 C10 C16 118.63(16) . . ?
C12 C11 H11 119.8 . . ?
C22 C11 H11 119.8 . . ?
C22 C11 C12 120.34(17) . . ?
C11 C12 P1 124.11(13) . . ?
C30 C12 P1 116.98(13) . . ?
C30 C12 C11 118.85(16) . . ?
O3 C16 N5 120.29(15) . . ?
O3 C16 C10 120.73(16) . . ?
N5 C16 C10 118.80(15) . . ?
C21 C18 H18 119.6 . . ?
C42 C18 H18 119.6 . . ?
C42 C18 C21 120.8(2) . . ?
C18 C21 P1 122.65(14) . . ?
C18 C21 C52 119.3(2) . . ?
C52 C21 P1 117.83(17) . . ?
C11 C22 H22 119.9 . . ?
C25 C22 C11 120.22(18) . . ?
C25 C22 H22 119.9 . . ?
C7 C23 H23 119.6 . . ?
C46 C23 C7 120.82(19) . . ?
C46 C23 H23 119.6 . . ?
C22 C25 H25 120.0 . . ?
C22 C25 C50 120.07(18) . . ?
C50 C25 H25 120.0 . . ?
C10 C26 H26 120.2 . . ?
C29 C26 C10 119.52(19) . . ?
C29 C26 H26 120.2 . . ?
C26 C29 H29 119.9 . . ?
C56 C29 C26 120.2(2) . . ?
C56 C29 H29 119.9 . . ?
C12 C30 H30 119.9 . . ?
C50 C30 C12 120.24(18) . . ?
C50 C30 H30 119.9 . . ?
C10 C31 H31 120.1 . . ?
C40 C31 C10 119.82(19) . . ?
C40 C31 H31 120.1 . . ?
C7 C38 H38 119.8 . . ?
C7 C38 C53 120.45(19) . . ?
C53 C38 H38 119.8 . . ?
C31 C40 H40 120.1 . . ?
C56 C40 C31 119.9(2) . . ?
C56 C40 H40 120.1 . . ?
C18 C42 H42 120.0 . . ?
C57 C42 C18 120.0(2) . . ?
C57 C42 H42 120.0 . . ?
N5 C43 C7 112.83(13) . . ?
N5 C43 H43A 109.0 . . ?
N5 C43 H43B 109.0 . . ?
C7 C43 H43A 109.0 . . ?
C7 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
C23 C46 H46 119.9 . . ?
C51 C46 C23 120.3(2) . . ?
C51 C46 H46 119.9 . . ?
C25 C50 C30 120.28(18) . . ?
C25 C50 H50 119.9 . . ?
C30 C50 H50 119.9 . . ?
C46 C51 H51 120.1 . . ?
C53 C51 C46 119.82(19) . . ?
C53 C51 H51 120.1 . . ?
C21 C52 H52 120.4 . . ?
C21 C52 C60 119.2(3) . . ?
C60 C52 H52 120.4 . . ?
C38 C53 H53 119.9 . . ?
C51 C53 C38 120.28(19) . . ?
C51 C53 H53 119.9 . . ?
C29 C56 H56 119.8 . . ?
C40 C56 C29 120.5(2) . . ?
C40 C56 H56 119.8 . . ?
C42 C57 H57 120.2 . . ?
C42 C57 C60 119.6(2) . . ?
C60 C57 H57 120.2 . . ?
C52 C60 H60 119.5 . . ?
C57 C60 C52 120.9(2) . . ?
C57 C60 H60 119.5 . . ?

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 N5 C16 O3 152.21(15) . . . . ?
P1 N5 C16 C10 -32.6(2) . . . . ?
P1 N5 C43 C7 111.53(15) . . . . ?
P1 C12 C30 C50 -177.34(16) . . . . ?
P1 C21 C52 C60 174.7(2) . . . . ?
O4 P1 N5 C16 99.43(15) . . . . ?
O4 P1 N5 C43 -81.66(14) . . . . ?
O4 P1 C12 C11 165.07(15) . . . . ?
O4 P1 C12 C30 -17.91(17) . . . . ?
O4 P1 C21 C18 168.55(15) . . . . ?
O4 P1 C21 C52 -6.3(2) . . . . ?
N5 P1 C12 C11 39.82(16) . . . . ?
N5 P1 C12 C30 -143.16(14) . . . . ?
N5 P1 C21 C18 -63.23(17) . . . . ?
N5 P1 C21 C52 121.89(17) . . . . ?
C7 C23 C46 C51 -0.1(3) . . . . ?
C7 C38 C53 C51 0.4(3) . . . . ?
C10 C26 C29 C56 -0.8(3) . . . . ?
C10 C31 C40 C56 -1.6(4) . . . . ?
C11 C12 C30 C50 -0.1(3) . . . . ?
C11 C22 C25 C50 0.0(3) . . . . ?
C12 P1 N5 C16 -138.29(14) . . . . ?
C12 P1 N5 C43 40.62(14) . . . . ?
C12 P1 C21 C18 46.76(17) . . . . ?
C12 P1 C21 C52 -128.11(17) . . . . ?
C12 C11 C22 C25 -0.1(3) . . . . ?
C12 C30 C50 C25 0.0(3) . . . . ?
C16 N5 C43 C7 -69.44(19) . . . . ?
C16 C10 C26 C29 -170.92(17) . . . . ?
C16 C10 C31 C40 172.31(19) . . . . ?
C18 C21 C52 C60 -0.3(4) . . . . ?
C18 C42 C57 C60 -0.6(4) . . . . ?
C21 P1 N5 C16 -27.00(16) . . . . ?
C21 P1 N5 C43 151.91(13) . . . . ?
C21 P1 C12 C11 -72.17(16) . . . . ?
C21 P1 C12 C30 104.86(15) . . . . ?
C21 C18 C42 C57 -1.1(4) . . . . ?
C21 C52 C60 C57 -1.4(5) . . . . ?
C22 C11 C12 P1 177.18(14) . . . . ?
C22 C11 C12 C30 0.2(3) . . . . ?
C22 C25 C50 C30 0.1(3) . . . . ?
C23 C7 C38 C53 -0.9(3) . . . . ?
C23 C7 C43 N5 -73.1(2) . . . . ?
C23 C46 C51 C53 -0.4(3) . . . . ?
C26 C10 C16 O3 134.39(19) . . . . ?
C26 C10 C16 N5 -40.8(2) . . . . ?
C26 C10 C31 C40 2.0(3) . . . . ?
C26 C29 C56 C40 1.3(4) . . . . ?
C31 C10 C16 O3 -35.9(2) . . . . ?
C31 C10 C16 N5 148.96(17) . . . . ?
C31 C10 C26 C29 -0.8(3) . . . . ?
C31 C40 C56 C29 0.0(4) . . . . ?
C38 C7 C23 C46 0.8(3) . . . . ?
C38 C7 C43 N5 109.55(18) . . . . ?
C42 C18 C21 P1 -173.26(17) . . . . ?
C42 C18 C21 C52 1.5(3) . . . . ?
C42 C57 C60 C52 1.8(5) . . . . ?
C43 N5 C16 O3 -26.7(2) . . . . ?
C43 N5 C16 C10 148.44(15) . . . . ?
C43 C7 C23 C46 -176.62(17) . . . . ?
C43 C7 C38 C53 176.44(17) . . . . ?
C46 C51 C53 C38 0.3(3) . . . . ?

_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 1.862
_oxdiff_exptl_absorpt_empirical_full_min 0.517
