# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_sjx-2-20200612
_database_code_depnum_ccdc_archive 'CCDC 2019969'
loop_
_audit_author_name
_audit_author_address
'jiaxuan shen'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_chemical_name_common            ?
_chemical_name_systematic        
'diphenyl(2-(pyridin-4-yl)-2-(o-tolyl)ethyl)phosphine oxide'
_chemical_formula_moiety         'C26 H24 N O P'
_chemical_formula_sum            'C26 H24 N O P'
_chemical_formula_weight         397.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.5237(3)
_cell_length_b                   21.1917(6)
_cell_length_c                   11.5154(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4276.32(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5440
_cell_measurement_temperature    295.66(13)
_cell_measurement_theta_max      71.3110
_cell_measurement_theta_min      5.0460
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11578
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.577
_diffrn_reflns_theta_min         4.172
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.66(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -19.00   1.00    4.02    --  -35.62  85.00-169.00   26
  2  ω    -97.00 -39.00   1.00    4.02    --  -35.62 138.00-108.00   58
  3  ω    -36.00 -10.00   1.00    4.02    --  -35.62 138.00-108.00   26
  4  ω     41.00 123.00   1.00   16.07    --  107.12-132.00   5.00   82
  5  ω     50.00 126.00   1.00   16.07    --  107.12 -37.00-129.00   76
  6  ω     99.00 127.00   1.00   16.07    --  107.12  85.00-169.00   28
  7  ω      2.00  29.00   1.00    4.02    --  -35.62  85.00-169.00   27
  8  ω    -92.00 -19.00   1.00    4.02    --  -35.62 -57.00   0.00   73
  9  ω     67.00  98.00   1.00    4.02    --   35.62 178.00-150.00   31
 10  ω    106.00 159.00   1.00   16.07    --  107.12 111.00 150.00   53
 11  ω     49.00 122.00   1.00   16.07    --  107.12 -45.00  90.00   73
 12  ω     48.00  85.00   1.00   16.07    --  107.12 -95.00   0.00   37
 13  ω     60.00  98.00   1.00   16.07    --  107.12 -85.00  71.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0512463000
_diffrn_orient_matrix_UB_12      -0.0550186000
_diffrn_orient_matrix_UB_13      0.0392665000
_diffrn_orient_matrix_UB_21      -0.0582247000
_diffrn_orient_matrix_UB_22      -0.0474646000
_diffrn_orient_matrix_UB_23      -0.0493886000
_diffrn_orient_matrix_UB_31      0.0413983000
_diffrn_orient_matrix_UB_32      0.0014727000
_diffrn_orient_matrix_UB_33      -0.1179988000
_diffrn_oxdiff_digest_frames     
;
0138d572917c1c5b0d881efb0fd7f244a100028c8b1
;
_diffrn_oxdiff_digest_hkl        
;
01d3320ca4ab485222f8e93f4fa1b76053f41a
;
_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                3459
_reflns_number_total             4072
_reflns_odcompleteness_completeness 99.88
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.679
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0929
_refine_ls_restrained_S_all      1.173
_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)+(0.0787P)²+8.7284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2386
_refine_ls_wR_factor_ref         0.2453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C4 \\sim C3 \\sim C2 \\sim C1 \\sim C6 \\sim C5 \\sim C11: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
Uanis(C11) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C4, C3, C2, C1, C6, C5, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C29(H29), C28(H28), C23(H23), C25(H25), C22(H22), C20(H20),
 C14(H14), C27(H27), C21(H21), C26(H26), C13(H13), C3(H3), C16(H16), C17(H17),
 C2(H2), C1(H1), C6(H6)
4.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
P9 P 0.23195(5) 0.22759(5) 0.75288(8) 0.0415(3) Uani 1 1 d . . . . .
O10 O 0.22440(18) 0.22667(16) 0.8821(2) 0.0569(8) Uani 1 1 d . . . . .
C24 C 0.1767(2) 0.16577(19) 0.6854(4) 0.0437(9) Uani 1 1 d . . . . .
C18 C 0.3296(2) 0.21644(19) 0.7081(3) 0.0442(9) Uani 1 1 d . . . . .
C8 C 0.1962(2) 0.29867(19) 0.6853(4) 0.0464(9) Uani 1 1 d . . . . .
H8A H 0.210258 0.297728 0.603827 0.056 Uiso 1 1 calc R . . . .
H8B H 0.140894 0.297804 0.689102 0.056 Uiso 1 1 calc R . . . .
C15 C 0.3071(2) 0.3735(2) 0.7111(4) 0.0497(10) Uani 1 1 d . . . . .
C7 C 0.2237(2) 0.3618(2) 0.7369(4) 0.0516(10) Uani 1 1 d . . . . .
H7 H 0.218293 0.358856 0.821393 0.062 Uiso 1 1 calc R . . . .
C19 C 0.3839(3) 0.2028(2) 0.7927(4) 0.0572(11) Uani 1 1 d . . . . .
H19 H 0.369001 0.198565 0.869751 0.069 Uiso 1 1 calc R . . . .
C29 C 0.1491(2) 0.1694(2) 0.5722(4) 0.0539(11) Uani 1 1 d . . . . .
H29 H 0.161136 0.204381 0.527095 0.065 Uiso 1 1 calc R . . . .
C28 C 0.1050(3) 0.1228(3) 0.5261(5) 0.0655(13) Uani 1 1 d . . . . .
H28 H 0.086747 0.126481 0.450525 0.079 Uiso 1 1 calc R . . . .
C23 C 0.3534(2) 0.2202(2) 0.5931(4) 0.0585(12) Uani 1 1 d . . . . .
H23 H 0.318021 0.228060 0.534655 0.070 Uiso 1 1 calc R . . . .
C25 C 0.1592(3) 0.1131(2) 0.7494(5) 0.0694(14) Uani 1 1 d . . . . .
H25 H 0.177529 0.109436 0.824852 0.083 Uiso 1 1 calc R . . . .
C4 C 0.1768(3) 0.4177(2) 0.6970(6) 0.0708(13) Uani 1 1 d . U . . .
C22 C 0.4296(3) 0.2123(3) 0.5657(5) 0.0704(15) Uani 1 1 d . . . . .
H22 H 0.444961 0.214627 0.488480 0.084 Uiso 1 1 calc R . . . .
C20 C 0.4594(3) 0.1956(3) 0.7633(5) 0.0718(15) Uani 1 1 d . . . . .
H20 H 0.495133 0.186777 0.820815 0.086 Uiso 1 1 calc R . . . .
C14 C 0.3324(3) 0.3829(2) 0.5985(4) 0.0614(12) Uani 1 1 d . . . . .
H14 H 0.297984 0.381428 0.537116 0.074 Uiso 1 1 calc R . . . .
C27 C 0.0875(3) 0.0709(3) 0.5908(6) 0.0783(17) Uani 1 1 d . . . . .
H27 H 0.057285 0.039047 0.559376 0.094 Uiso 1 1 calc R . . . .
C21 C 0.4825(3) 0.2012(3) 0.6499(5) 0.0718(15) Uani 1 1 d . . . . .
H21 H 0.533870 0.197435 0.630762 0.086 Uiso 1 1 calc R . . . .
N12 N 0.4607(3) 0.3980(3) 0.6572(7) 0.1034(19) Uani 1 1 d . . . . .
C26 C 0.1147(4) 0.0655(2) 0.7031(7) 0.0887(19) Uani 1 1 d . . . . .
H26 H 0.103094 0.030059 0.747261 0.106 Uiso 1 1 calc R . . . .
C13 C 0.4079(3) 0.3941(3) 0.5777(6) 0.0823(18) Uani 1 1 d . . . . .
H13 H 0.422809 0.399525 0.500801 0.099 Uiso 1 1 calc R . . . .
C3 C 0.1352(3) 0.4147(3) 0.5937(6) 0.0874(17) Uani 1 1 d . U . . .
H3 H 0.134837 0.377691 0.550409 0.105 Uiso 1 1 calc R . . . .
C16 C 0.3621(4) 0.3767(3) 0.7963(5) 0.0899(19) Uani 1 1 d . . . . .
H16 H 0.349153 0.370496 0.873780 0.108 Uiso 1 1 calc R . . . .
C5 C 0.1784(4) 0.4733(3) 0.7630(8) 0.1006(19) Uani 1 1 d . U . . .
C17 C 0.4377(4) 0.3894(4) 0.7650(8) 0.111(3) Uani 1 1 d . . . . .
H17 H 0.473942 0.391967 0.823813 0.134 Uiso 1 1 calc R . . . .
C2 C 0.0939(4) 0.4677(4) 0.5549(9) 0.117(2) Uani 1 1 d . U . . .
H2 H 0.065790 0.466040 0.486501 0.141 Uiso 1 1 calc R . . . .
C11 C 0.2286(5) 0.4798(4) 0.8761(8) 0.131(3) Uani 1 1 d . U . . .
H11A H 0.220167 0.443994 0.925437 0.197 Uiso 1 1 calc GR . . . .
H11B H 0.214533 0.517671 0.916713 0.197 Uiso 1 1 calc GR . . . .
H11C H 0.281511 0.481878 0.855020 0.197 Uiso 1 1 calc GR . . . .
C1 C 0.0961(6) 0.5209(5) 0.6193(11) 0.141(3) Uani 1 1 d . U . . .
H1 H 0.069453 0.556155 0.593467 0.170 Uiso 1 1 calc R . . . .
C6 C 0.1352(6) 0.5248(4) 0.7192(10) 0.134(3) Uani 1 1 d . U . . .
H6 H 0.133998 0.562358 0.761076 0.160 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P9 O10 1.494(3) . ?
P9 C24 1.805(4) . ?
P9 C18 1.803(4) . ?
P9 C8 1.808(4) . ?
C24 C29 1.391(6) . ?
C24 C25 1.372(6) . ?
C18 C19 1.392(6) . ?
C18 C23 1.390(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.541(6) . ?
C15 C7 1.513(6) . ?
C15 C14 1.384(6) . ?
C15 C16 1.377(7) . ?
C7 H7 0.9800 . ?
C7 C4 1.513(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(7) . ?
C29 H29 0.9300 . ?
C29 C28 1.361(6) . ?
C28 H28 0.9300 . ?
C28 C27 1.365(8) . ?
C23 H23 0.9300 . ?
C23 C22 1.382(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(7) . ?
C4 C3 1.397(9) . ?
C4 C5 1.402(9) . ?
C22 H22 0.9300 . ?
C22 C21 1.363(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.366(7) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(9) . ?
C21 H21 0.9300 . ?
N12 C13 1.304(8) . ?
N12 C17 1.317(10) . ?
C26 H26 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.408(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(10) . ?
C5 C11 1.577(12) . ?
C5 C6 1.422(11) . ?
C17 H17 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.350(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C6 1.342(14) . ?
C6 H6 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
O10 P9 C24 111.83(19) . . ?
O10 P9 C18 111.56(18) . . ?
O10 P9 C8 114.14(19) . . ?
C24 P9 C8 103.47(19) . . ?
C18 P9 C24 106.93(18) . . ?
C18 P9 C8 108.37(19) . . ?
C29 C24 P9 123.3(3) . . ?
C25 C24 P9 118.6(3) . . ?
C25 C24 C29 118.1(4) . . ?
C19 C18 P9 118.4(3) . . ?
C23 C18 P9 123.3(3) . . ?
C23 C18 C19 118.2(4) . . ?
P9 C8 H8A 108.1 . . ?
P9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C7 C8 P9 116.7(3) . . ?
C7 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C14 C15 C7 121.1(4) . . ?
C16 C15 C7 123.0(5) . . ?
C16 C15 C14 115.9(5) . . ?
C8 C7 H7 107.3 . . ?
C15 C7 C8 111.7(3) . . ?
C15 C7 H7 107.3 . . ?
C15 C7 C4 109.6(4) . . ?
C4 C7 C8 113.2(4) . . ?
C4 C7 H7 107.3 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(4) . . ?
C20 C19 H19 119.7 . . ?
C24 C29 H29 119.2 . . ?
C28 C29 C24 121.5(5) . . ?
C28 C29 H29 119.2 . . ?
C29 C28 H28 120.0 . . ?
C29 C28 C27 120.0(5) . . ?
C27 C28 H28 120.0 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.8(5) . . ?
C26 C25 H25 119.6 . . ?
C3 C4 C7 120.4(5) . . ?
C3 C4 C5 120.7(6) . . ?
C5 C4 C7 118.9(6) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 C23 121.0(5) . . ?
C21 C22 H22 119.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C28 C27 H27 120.0 . . ?
C28 C27 C26 119.9(5) . . ?
C26 C27 H27 120.0 . . ?
C22 C21 C20 119.4(5) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C13 N12 C17 115.9(6) . . ?
C25 C26 C27 119.7(6) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C14 C13 H13 117.5 . . ?
N12 C13 C14 125.1(6) . . ?
N12 C13 H13 117.5 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.2(7) . . ?
C2 C3 H3 119.9 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C4 C5 C11 122.2(7) . . ?
C4 C5 C6 116.3(9) . . ?
C6 C5 C11 121.4(8) . . ?
N12 C17 C16 124.0(6) . . ?
N12 C17 H17 118.0 . . ?
C16 C17 H17 118.0 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.5(10) . . ?
C1 C2 H2 120.8 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C1 H1 118.7 . . ?
C6 C1 C2 122.5(9) . . ?
C6 C1 H1 118.7 . . ?
C5 C6 H6 119.1 . . ?
C1 C6 C5 121.9(9) . . ?
C1 C6 H6 119.1 . . ?

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
P9 C24 C29 C28 -177.3(3) . . . . ?
P9 C24 C25 C26 177.6(5) . . . . ?
P9 C18 C19 C20 -178.3(4) . . . . ?
P9 C18 C23 C22 178.7(4) . . . . ?
P9 C8 C7 C15 70.3(4) . . . . ?
P9 C8 C7 C4 -165.3(3) . . . . ?
O10 P9 C24 C29 154.2(3) . . . . ?
O10 P9 C24 C25 -24.2(4) . . . . ?
O10 P9 C18 C19 5.8(4) . . . . ?
O10 P9 C18 C23 -174.8(4) . . . . ?
O10 P9 C8 C7 49.6(3) . . . . ?
C24 P9 C18 C19 -116.8(4) . . . . ?
C24 P9 C18 C23 62.6(4) . . . . ?
C24 P9 C8 C7 171.4(3) . . . . ?
C24 C29 C28 C27 -0.7(7) . . . . ?
C24 C25 C26 C27 0.1(9) . . . . ?
C18 P9 C24 C29 -83.4(4) . . . . ?
C18 P9 C24 C25 98.2(4) . . . . ?
C18 P9 C8 C7 -75.4(3) . . . . ?
C18 C19 C20 C21 -0.5(9) . . . . ?
C18 C23 C22 C21 -0.4(9) . . . . ?
C8 P9 C24 C29 30.9(4) . . . . ?
C8 P9 C24 C25 -147.5(4) . . . . ?
C8 P9 C18 C19 132.3(4) . . . . ?
C8 P9 C18 C23 -48.3(4) . . . . ?
C8 C7 C4 C3 -23.0(6) . . . . ?
C8 C7 C4 C5 159.6(4) . . . . ?
C15 C7 C4 C3 102.4(5) . . . . ?
C15 C7 C4 C5 -74.9(5) . . . . ?
C15 C14 C13 N12 -1.0(10) . . . . ?
C15 C16 C17 N12 -0.9(13) . . . . ?
C7 C15 C14 C13 179.2(5) . . . . ?
C7 C15 C16 C17 -178.3(6) . . . . ?
C7 C4 C3 C2 -177.7(5) . . . . ?
C7 C4 C5 C11 1.0(8) . . . . ?
C7 C4 C5 C6 178.0(5) . . . . ?
C19 C18 C23 C22 -1.8(7) . . . . ?
C19 C20 C21 C22 -1.8(9) . . . . ?
C29 C24 C25 C26 -0.8(8) . . . . ?
C29 C28 C27 C26 -0.1(8) . . . . ?
C28 C27 C26 C25 0.3(9) . . . . ?
C23 C18 C19 C20 2.3(7) . . . . ?
C23 C22 C21 C20 2.3(9) . . . . ?
C25 C24 C29 C28 1.1(6) . . . . ?
C4 C3 C2 C1 0.5(11) . . . . ?
C4 C5 C6 C1 -1.1(12) . . . . ?
C14 C15 C7 C8 65.6(6) . . . . ?
C14 C15 C7 C4 -60.6(6) . . . . ?
C14 C15 C16 C17 0.6(9) . . . . ?
C13 N12 C17 C16 0.2(12) . . . . ?
C3 C4 C5 C11 -176.3(6) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C3 C2 C1 C6 -0.9(15) . . . . ?
C16 C15 C7 C8 -115.4(5) . . . . ?
C16 C15 C7 C4 118.3(6) . . . . ?
C16 C15 C14 C13 0.2(8) . . . . ?
C5 C4 C3 C2 -0.4(8) . . . . ?
C17 N12 C13 C14 0.7(11) . . . . ?
C2 C1 C6 C5 1.3(16) . . . . ?
C11 C5 C6 C1 175.9(8) . . . . ?

_shelx_SHELXL_version_number     2018/3
_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 2.164
_oxdiff_exptl_absorpt_empirical_full_min 0.534
####################################################################### 
# 
# 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_sjx-20200811
_database_code_depnum_ccdc_archive 'CCDC 2024091'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Shen'
;Henan Normal University
China
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H29 N O P'
_chemical_formula_sum            'C34 H29 N O P'
_chemical_formula_weight         498.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.7999(3)
_cell_length_b                   19.4353(13)
_cell_length_c                   24.2505(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.818(5)
_cell_angle_gamma                90
_cell_volume                     2733.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4515
_cell_measurement_temperature    295.50(11)
_cell_measurement_theta_max      26.0830
_cell_measurement_theta_min      3.7650
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18737
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.105
_diffrn_reflns_theta_min         3.361
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.50(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  44.00   1.00    4.99    --   16.29 -95.00  96.00   26
  2  ω    -50.00 -25.00   1.00    4.99    --  -16.91  95.00-153.00   25
  3  ω     37.00  88.00   1.00    4.99    --   16.29 178.00-120.00   51
  4  ω    -38.00  33.00   1.00    4.99    --   16.29 -57.00  30.00   71
  5  ω      3.00  58.00   1.00    4.99    --   16.29  57.00-180.00   55
  6  ω     41.00  87.00   1.00    4.99    --   16.29 178.00 -60.00   46
  7  ω     36.00  83.00   1.00    4.99    --   16.29 178.00  30.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0681903000
_diffrn_orient_matrix_UB_12      -0.0298916000
_diffrn_orient_matrix_UB_13      -0.0041951000
_diffrn_orient_matrix_UB_21      -0.0569830000
_diffrn_orient_matrix_UB_22      0.0161998000
_diffrn_orient_matrix_UB_23      -0.0225945000
_diffrn_orient_matrix_UB_31      0.0840810000
_diffrn_orient_matrix_UB_32      -0.0132707000
_diffrn_orient_matrix_UB_33      -0.0180849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4097
_reflns_number_total             6417
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         6417
_refine_ls_number_restraints     486
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1022
_refine_ls_restrained_S_all      1.097
_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)+(0.1408P)²+3.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2707
_refine_ls_wR_factor_ref         0.3051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C9-C8A
 1.49 with sigma of 0.01
 C8A-C7A
 1.4 with sigma of 0.01
 C9-C7A
 2.47 with sigma of 0.01
 C7A-C1A
 1.479 with sigma of 0.01
 C8A-C1A
 2.558 with sigma of 0.01
 C7A-C2A
 2.745 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim N5 \\sim C3 \\sim C2 \\sim C6 \\sim C4 \\sim C1A \\sim C6A \\sim C4A
\\sim N5A \\sim C3A \\sim C2A \\sim C7 \\sim C7A \\sim C8 \\sim C8A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C3) \\sim Ueq, Uanis(N5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C7A) \\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C1, N5, C3, C2, C6, C4, C1A, C6A, C4A, N5A, C3A, C2A, C7, C7A, C8, C8A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15, C14, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C32, C13, C20, C21, C12, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H9B)=Sof(C1A)=Sof(C6A)=Sof(H6A)=Sof(C4A)=Sof(H4A)=Sof(N5A)=Sof(C3A)=
 Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(C1)=Sof(H9A)=Sof(C8)=Sof(H8)=Sof(N5)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C4)=Sof(H4)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
6.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C18(H18), C17(H17), C16(H16), C9(H9A), C9(H9B), C8(H8),
 C3(H3), C2(H2), C6(H6), C4(H4), C6A(H6A), C4A(H4A), C3A(H3A), C2A(H2A),
 C8A(H8A), C13(H13), C5(H5), C21(H21), C24(H24), C22(H22), C26(H26), C12(H12),
 C20(H20), C27(H27), C34(H34), C33(H33), C28(H28), C29(H29), C30(H30)
6.d Fitted hexagon refined as free rotating group:
 C15(C14,C19,C18,C17,C16), C1A(C6A,C4A,N5A,C3A,C2A)
;
_atom_sites_solution_hydrogens   mixed
_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
P12 P 0.53364(14) 0.70601(5) 0.17527(4) 0.0435(3) Uani 1 1 d . . . . .
O13 O 0.7839(4) 0.70669(15) 0.18844(12) 0.0597(7) Uani 1 1 d . . . . .
C32 C 0.4355(6) 0.62355(19) 0.15081(15) 0.0504(8) Uani 1 1 d . . . . .
C11 C 0.3546(6) 0.7254(2) 0.23373(14) 0.0490(8) Uani 1 1 d . . . . .
H11A H 0.196890 0.732078 0.220962 0.059 Uiso 1 1 calc R U . . .
H11B H 0.356509 0.686537 0.258794 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4341(6) 0.7894(2) 0.26470(14) 0.0508(9) Uani 1 1 d . . . . .
C1 C 0.8739(13) 0.7743(4) 0.4125(3) 0.0553(13) Uani 0.627(6) 1 d . U P A 1
C15 C 1.1319(6) 0.63075(18) 0.36939(13) 0.0961(15) Uani 1 1 d G . . . .
H15 H 1.208677 0.658872 0.344635 0.115 Uiso 1 1 calc R U . . .
C14 C 0.9227(7) 0.65174(14) 0.39104(14) 0.0813(12) Uani 1 1 d G . . . .
C19 C 0.8079(5) 0.60971(19) 0.42803(14) 0.0944(15) Uani 1 1 d G . . . .
H19 H 0.667996 0.623756 0.442522 0.113 Uiso 1 1 calc R U . . .
C18 C 0.9023(6) 0.54670(17) 0.44337(14) 0.1025(17) Uani 1 1 d G . . . .
H18 H 0.825558 0.518586 0.468126 0.123 Uiso 1 1 calc R U . . .
C17 C 1.1115(6) 0.52572(14) 0.42172(15) 0.0803(12) Uani 1 1 d G . . . .
H17 H 1.174679 0.483559 0.431985 0.096 Uiso 1 1 calc R U . . .
C16 C 1.2263(5) 0.5677(2) 0.38473(14) 0.0994(15) Uani 1 1 d G . . . .
H16 H 1.366242 0.553701 0.370240 0.119 Uiso 1 1 calc R U . . .
C9 C 0.5874(8) 0.7844(2) 0.30607(17) 0.0709(13) Uani 1 1 d D . . . .
H9A H 0.640974 0.825084 0.321847 0.085 Uiso 0.627(6) 1 calc R U P A 1
H9B H 0.581542 0.818870 0.332608 0.085 Uiso 0.373(6) 1 calc R U P A 2
C8 C 0.6804(14) 0.7175(4) 0.3292(4) 0.0681(18) Uani 0.627(6) 1 d . U P A 1
H8 H 0.687329 0.677992 0.307674 0.082 Uiso 0.627(6) 1 calc R U P A 1
N5 N 0.9615(15) 0.8692(5) 0.4946(4) 0.0979(18) Uani 0.627(6) 1 d . U P A 1
C3 C 1.1263(18) 0.8572(5) 0.4560(4) 0.0930(19) Uani 0.627(6) 1 d . U P A 1
H3 H 1.267321 0.879917 0.457857 0.112 Uiso 0.627(6) 1 calc R U P A 1
C2 C 1.0782(15) 0.8099(5) 0.4135(4) 0.0804(17) Uani 0.627(6) 1 d . U P A 1
H2 H 1.185425 0.802765 0.385913 0.097 Uiso 0.627(6) 1 calc R U P A 1
C6 C 0.7202(16) 0.7877(5) 0.4511(4) 0.0793(17) Uani 0.627(6) 1 d . U P A 1
H6 H 0.580560 0.764159 0.450234 0.095 Uiso 0.627(6) 1 calc R U P A 1
C7 C 0.7541(14) 0.7177(4) 0.3831(3) 0.0642(15) Uani 0.627(6) 1 d . U P A 1
H7 H 0.617115 0.707519 0.404844 0.077 Uiso 0.627(6) 1 calc R U P A 1
C4 C 0.7578(17) 0.8331(5) 0.4909(4) 0.0889(19) Uani 0.627(6) 1 d . U P A 1
H4 H 0.644077 0.840845 0.516802 0.107 Uiso 0.627(6) 1 calc R U P A 1
C1A C 0.9135(17) 0.7820(5) 0.4053(3) 0.0664(19) Uani 0.373(6) 1 d DG U P A 2
C6A C 0.8328(18) 0.7910(5) 0.4585(4) 0.085(2) Uani 0.373(6) 1 d G U P A 2
H6A H 0.715489 0.762989 0.471535 0.102 Uiso 0.373(6) 1 calc R U P A 2
C4A C 0.927(2) 0.8418(6) 0.4922(3) 0.098(2) Uani 0.373(6) 1 d G U P A 2
H4A H 0.873518 0.847732 0.527855 0.118 Uiso 0.373(6) 1 calc R U P A 2
N5A N 1.1028(19) 0.8836(5) 0.4728(4) 0.101(3) Uani 0.373(6) 1 d G U P A 2
C3A C 1.1835(15) 0.8746(5) 0.4195(4) 0.094(3) Uani 0.373(6) 1 d G U P A 2
H3A H 1.300791 0.902639 0.406513 0.112 Uiso 0.373(6) 1 calc R U P A 2
C2A C 1.0888(16) 0.8239(5) 0.3858(3) 0.083(2) Uani 0.373(6) 1 d DG U P A 2
H2A H 1.142763 0.817896 0.350191 0.099 Uiso 0.373(6) 1 calc R U P A 2
C7A C 0.8629(19) 0.7169(4) 0.3659(4) 0.0614(19) Uani 0.373(6) 1 d D U P A 2
H7A H 1.017915 0.720545 0.350539 0.074 Uiso 0.373(6) 1 calc R U P A 2
C8A C 0.7671(19) 0.7304(5) 0.3150(4) 0.055(2) Uani 0.373(6) 1 d D U P A 2
H8A H 0.815984 0.704942 0.284933 0.066 Uiso 0.373(6) 1 calc R U P A 2
C25 C 0.4582(6) 0.76654(19) 0.12160(14) 0.0457(8) Uani 1 1 d . . . . .
C23 C 0.3379(6) 0.8569(2) 0.24763(14) 0.0511(9) Uani 1 1 d . . . . .
C13 C 0.5847(9) 0.5874(3) 0.1175(2) 0.0816(14) Uani 1 1 d . . . . .
H13 H 0.728422 0.605846 0.109602 0.098 Uiso 1 1 calc R U . . .
C5 C 0.2266(7) 0.5936(2) 0.1632(2) 0.0734(13) Uani 1 1 d . . . . .
H5 H 0.124213 0.616675 0.185844 0.088 Uiso 1 1 calc R U . . .
C21 C 0.3163(11) 0.4957(3) 0.1086(3) 0.0991(18) Uani 1 1 d . . . . .
H21 H 0.276291 0.452854 0.094234 0.119 Uiso 1 1 calc R U . . .
C24 C 0.6097(8) 0.8189(3) 0.11038(19) 0.0726(13) Uani 1 1 d . . . . .
H24 H 0.749027 0.821995 0.129681 0.087 Uiso 1 1 calc R U . . .
C22 C 0.1257(8) 0.8634(2) 0.2212(2) 0.0729(13) Uani 1 1 d . . . . .
H22 H 0.037127 0.824377 0.214356 0.087 Uiso 1 1 calc R U . . .
C26 C 0.2543(7) 0.7626(3) 0.09220(19) 0.0720(13) Uani 1 1 d . . . . .
H26 H 0.150061 0.727619 0.099711 0.086 Uiso 1 1 calc R U . . .
C12 C 0.1680(9) 0.5297(3) 0.1423(3) 0.0943(17) Uani 1 1 d . . . . .
H12 H 0.027480 0.509838 0.151164 0.113 Uiso 1 1 calc R U . . .
C20 C 0.5223(13) 0.5245(3) 0.0961(3) 0.111(2) Uani 1 1 d . . . . .
H20 H 0.622267 0.501437 0.072842 0.133 Uiso 1 1 calc R U . . .
C27 C 0.4602(10) 0.9171(3) 0.2565(2) 0.0856(16) Uani 1 1 d . . . . .
H27 H 0.605522 0.914566 0.273073 0.103 Uiso 1 1 calc R U . . .
C34 C 0.2031(9) 0.8102(3) 0.0517(2) 0.0896(16) Uani 1 1 d . . . . .
H34 H 0.065561 0.806782 0.031703 0.108 Uiso 1 1 calc R U . . .
C33 C 0.3546(10) 0.8624(3) 0.0409(2) 0.0870(16) Uani 1 1 d . . . . .
H33 H 0.320458 0.894482 0.013504 0.104 Uiso 1 1 calc R U . . .
C28 C 0.3748(11) 0.9805(3) 0.2416(3) 0.106(2) Uani 1 1 d . . . . .
H28 H 0.460269 1.019963 0.249265 0.128 Uiso 1 1 calc R U . . .
C29 C 0.1675(12) 0.9859(3) 0.2159(3) 0.105(2) Uani 1 1 d . . . . .
H29 H 0.109539 1.028838 0.205882 0.126 Uiso 1 1 calc R U . . .
C31 C 0.5545(12) 0.8671(3) 0.0704(3) 0.0983(19) Uani 1 1 d . . . . .
C30 C 0.0435(10) 0.9273(3) 0.2048(3) 0.0999(19) Uani 1 1 d . . . . .
H30 H -0.097107 0.930437 0.186043 0.120 Uiso 1 1 calc R U . . .
H31 H 0.655(11) 0.898(4) 0.060(3) 0.13(2) 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
P12 O13 1.482(2) . ?
P12 C32 1.799(4) . ?
P12 C11 1.809(4) . ?
P12 C25 1.804(4) . ?
C32 C13 1.383(6) . ?
C32 C5 1.381(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.520(5) . ?
C10 C9 1.335(5) . ?
C10 C23 1.483(5) . ?
C1 C2 1.373(11) . ?
C1 C6 1.328(11) . ?
C1 C7 1.479(10) . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C15 C16 1.3900 . ?
C14 C19 1.3900 . ?
C14 C7 1.622(8) . ?
C14 C7A 1.446(8) . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C9 C8 1.511(9) . ?
C9 C8A 1.493(8) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(10) . ?
N5 C3 1.367(12) . ?
N5 C4 1.375(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.407(13) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C6 C4 1.323(12) . ?
C7 H7 0.9800 . ?
C4 H4 0.9300 . ?
C1A C6A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A C7A 1.611(7) . ?
C6A H6A 0.9300 . ?
C6A C4A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A N5A 1.3900 . ?
N5A C3A 1.3900 . ?
C3A H3A 0.9300 . ?
C3A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C7A H7A 0.9800 . ?
C7A C8A 1.370(8) . ?
C8A H8A 0.9300 . ?
C25 C24 1.375(6) . ?
C25 C26 1.374(5) . ?
C23 C22 1.385(5) . ?
C23 C27 1.383(6) . ?
C13 H13 0.9300 . ?
C13 C20 1.376(7) . ?
C5 H5 0.9300 . ?
C5 C12 1.382(7) . ?
C21 H21 0.9300 . ?
C21 C12 1.365(8) . ?
C21 C20 1.358(8) . ?
C24 H24 0.9300 . ?
C24 C31 1.382(7) . ?
C22 H22 0.9300 . ?
C22 C30 1.386(7) . ?
C26 H26 0.9300 . ?
C26 C34 1.377(6) . ?
C12 H12 0.9300 . ?
C20 H20 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.375(7) . ?
C34 H34 0.9300 . ?
C34 C33 1.371(8) . ?
C33 H33 0.9300 . ?
C33 C31 1.357(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.350(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.373(8) . ?
C31 H31 0.88(7) . ?
C30 H30 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
O13 P12 C32 112.55(17) . . ?
O13 P12 C11 113.62(16) . . ?
O13 P12 C25 112.11(16) . . ?
C32 P12 C11 105.18(18) . . ?
C32 P12 C25 105.71(17) . . ?
C25 P12 C11 107.06(16) . . ?
C13 C32 P12 116.6(3) . . ?
C5 C32 P12 125.3(3) . . ?
C5 C32 C13 118.1(4) . . ?
P12 C11 H11A 109.1 . . ?
P12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 P12 112.6(3) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 C23 121.2(4) . . ?
C23 C10 C11 118.4(3) . . ?
C2 C1 C7 141.6(7) . . ?
C6 C1 C2 118.4(8) . . ?
C6 C1 C7 99.8(7) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C7 135.6(4) . . ?
C15 C14 C7A 107.6(6) . . ?
C19 C14 C15 120.0 . . ?
C19 C14 C7 104.3(4) . . ?
C19 C14 C7A 132.3(6) . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C10 C9 H9A 117.6 . . ?
C10 C9 H9B 115.9 . . ?
C10 C9 C8 124.8(5) . . ?
C10 C9 C8A 128.1(5) . . ?
C8 C9 H9A 117.6 . . ?
C8A C9 H9B 115.9 . . ?
C9 C8 H8 121.4 . . ?
C7 C8 C9 117.2(7) . . ?
C7 C8 H8 121.4 . . ?
C3 N5 C4 118.4(9) . . ?
N5 C3 H3 120.6 . . ?
N5 C3 C2 118.7(9) . . ?
C2 C3 H3 120.6 . . ?
C1 C2 C3 120.3(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C1 C6 H6 118.7 . . ?
C4 C6 C1 122.7(9) . . ?
C4 C6 H6 118.7 . . ?
C1 C7 C14 104.6(5) . . ?
C1 C7 H7 105.6 . . ?
C14 C7 H7 105.6 . . ?
C8 C7 C1 126.8(7) . . ?
C8 C7 C14 106.9(6) . . ?
C8 C7 H7 105.6 . . ?
N5 C4 H4 119.3 . . ?
C6 C4 N5 121.4(9) . . ?
C6 C4 H4 119.3 . . ?
C6A C1A C2A 120.0 . . ?
C6A C1A C7A 126.1(6) . . ?
C2A C1A C7A 112.7(6) . . ?
C1A C6A H6A 120.0 . . ?
C1A C6A C4A 120.0 . . ?
C4A C6A H6A 120.0 . . ?
C6A C4A H4A 120.0 . . ?
N5A C4A C6A 120.0 . . ?
N5A C4A H4A 120.0 . . ?
C4A N5A C3A 120.0 . . ?
N5A C3A H3A 120.0 . . ?
C2A C3A N5A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C14 C7A C1A 113.4(6) . . ?
C14 C7A H7A 90.5 . . ?
C1A C7A H7A 90.5 . . ?
C8A C7A C14 129.8(7) . . ?
C8A C7A C1A 116.8(7) . . ?
C8A C7A H7A 90.5 . . ?
C9 C8A H8A 118.7 . . ?
C7A C8A C9 122.7(7) . . ?
C7A C8A H8A 118.7 . . ?
C24 C25 P12 118.5(3) . . ?
C26 C25 P12 122.4(3) . . ?
C26 C25 C24 119.1(4) . . ?
C22 C23 C10 122.6(4) . . ?
C27 C23 C10 121.0(4) . . ?
C27 C23 C22 116.4(4) . . ?
C32 C13 H13 119.7 . . ?
C20 C13 C32 120.6(5) . . ?
C20 C13 H13 119.7 . . ?
C32 C5 H5 119.6 . . ?
C32 C5 C12 120.7(5) . . ?
C12 C5 H5 119.6 . . ?
C12 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C12 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C25 C24 C31 119.9(5) . . ?
C31 C24 H24 120.1 . . ?
C23 C22 H22 119.5 . . ?
C23 C22 C30 121.0(5) . . ?
C30 C22 H22 119.5 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C34 120.5(4) . . ?
C34 C26 H26 119.7 . . ?
C5 C12 H12 120.0 . . ?
C21 C12 C5 120.1(5) . . ?
C21 C12 H12 120.0 . . ?
C13 C20 H20 119.7 . . ?
C21 C20 C13 120.7(6) . . ?
C21 C20 H20 119.7 . . ?
C23 C27 H27 118.8 . . ?
C28 C27 C23 122.4(5) . . ?
C28 C27 H27 118.8 . . ?
C26 C34 H34 120.0 . . ?
C33 C34 C26 120.1(5) . . ?
C33 C34 H34 120.0 . . ?
C34 C33 H33 120.2 . . ?
C31 C33 C34 119.6(5) . . ?
C31 C33 H33 120.2 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(5) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.1(5) . . ?
C30 C29 H29 120.4 . . ?
C24 C31 H31 121(4) . . ?
C33 C31 C24 120.8(5) . . ?
C33 C31 H31 118(4) . . ?
C22 C30 H30 119.7 . . ?
C29 C30 C22 120.7(5) . . ?
C29 C30 H30 119.7 . . ?

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
P12 C32 C13 C20 -178.8(5) . . . . ?
P12 C32 C5 C12 -179.8(4) . . . . ?
P12 C11 C10 C9 -89.7(4) . . . . ?
P12 C11 C10 C23 90.1(4) . . . . ?
P12 C25 C24 C31 -178.5(5) . . . . ?
P12 C25 C26 C34 179.7(4) . . . . ?
O13 P12 C32 C13 -36.9(4) . . . . ?
O13 P12 C32 C5 142.1(4) . . . . ?
O13 P12 C11 C10 48.8(3) . . . . ?
O13 P12 C25 C24 -18.9(4) . . . . ?
O13 P12 C25 C26 162.0(4) . . . . ?
C32 P12 C11 C10 172.3(2) . . . . ?
C32 P12 C25 C24 -141.9(4) . . . . ?
C32 P12 C25 C26 39.0(4) . . . . ?
C32 C13 C20 C21 -2.1(10) . . . . ?
C32 C5 C12 C21 -0.6(9) . . . . ?
C11 P12 C32 C13 -161.1(3) . . . . ?
C11 P12 C32 C5 17.9(4) . . . . ?
C11 P12 C25 C24 106.3(4) . . . . ?
C11 P12 C25 C26 -72.8(4) . . . . ?
C11 C10 C9 C8 -5.3(8) . . . . ?
C11 C10 C9 C8A 26.2(10) . . . . ?
C11 C10 C23 C22 25.2(5) . . . . ?
C11 C10 C23 C27 -153.4(4) . . . . ?
C10 C9 C8 C7 -153.2(6) . . . . ?
C10 C9 C8A C7A -158.0(9) . . . . ?
C10 C23 C22 C30 -178.6(5) . . . . ?
C10 C23 C27 C28 -179.4(5) . . . . ?
C1 C6 C4 N5 -0.4(14) . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C15 C14 C7 C1 -74.0(6) . . . . ?
C15 C14 C7 C8 62.6(7) . . . . ?
C15 C14 C7A C1A -102.0(7) . . . . ?
C15 C14 C7A C8A 79.6(13) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C14 C7A C8A C9 139.9(11) . . . . ?
C19 C14 C7 C1 108.0(5) . . . . ?
C19 C14 C7 C8 -115.4(6) . . . . ?
C19 C14 C7A C1A 81.2(8) . . . . ?
C19 C14 C7A C8A -97.1(13) . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C16 C15 C14 C19 0.0 . . . . ?
C16 C15 C14 C7 -177.8(5) . . . . ?
C16 C15 C14 C7A -177.2(4) . . . . ?
C9 C10 C23 C22 -155.1(5) . . . . ?
C9 C10 C23 C27 26.4(6) . . . . ?
C9 C8 C7 C1 -36.5(12) . . . . ?
C9 C8 C7 C14 -160.4(6) . . . . ?
N5 C3 C2 C1 -3.0(14) . . . . ?
C3 N5 C4 C6 0.2(15) . . . . ?
C2 C1 C6 C4 -1.1(13) . . . . ?
C2 C1 C7 C14 57.9(13) . . . . ?
C2 C1 C7 C8 -67.0(15) . . . . ?
C6 C1 C2 C3 2.8(13) . . . . ?
C6 C1 C7 C14 -117.3(7) . . . . ?
C6 C1 C7 C8 117.8(9) . . . . ?
C7 C1 C2 C3 -171.9(10) . . . . ?
C7 C1 C6 C4 175.6(8) . . . . ?
C7 C14 C19 C18 178.4(3) . . . . ?
C4 N5 C3 C2 1.5(14) . . . . ?
C1A C6A C4A N5A 0.0 . . . . ?
C1A C7A C8A C9 -38.4(15) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C6A C1A C7A C14 -54.1(12) . . . . ?
C6A C1A C7A C8A 124.4(10) . . . . ?
C6A C4A N5A C3A 0.0 . . . . ?
C4A N5A C3A C2A 0.0 . . . . ?
N5A C3A C2A C1A 0.0 . . . . ?
C2A C1A C6A C4A 0.0 . . . . ?
C2A C1A C7A C14 113.0(9) . . . . ?
C2A C1A C7A C8A -68.5(11) . . . . ?
C7A C14 C19 C18 176.4(5) . . . . ?
C7A C1A C6A C4A 166.2(10) . . . . ?
C7A C1A C2A C3A -168.0(8) . . . . ?
C25 P12 C32 C13 85.8(4) . . . . ?
C25 P12 C32 C5 -95.2(4) . . . . ?
C25 P12 C11 C10 -75.5(3) . . . . ?
C25 C24 C31 C33 -1.7(10) . . . . ?
C25 C26 C34 C33 -0.8(9) . . . . ?
C23 C10 C9 C8 175.0(5) . . . . ?
C23 C10 C9 C8A -153.5(8) . . . . ?
C23 C22 C30 C29 -2.0(9) . . . . ?
C23 C27 C28 C29 -2.0(10) . . . . ?
C13 C32 C5 C12 -0.8(7) . . . . ?
C5 C32 C13 C20 2.1(8) . . . . ?
C24 C25 C26 C34 0.6(7) . . . . ?
C22 C23 C27 C28 2.0(8) . . . . ?
C26 C25 C24 C31 0.6(8) . . . . ?
C26 C34 C33 C31 -0.2(10) . . . . ?
C12 C21 C20 C13 0.7(11) . . . . ?
C20 C21 C12 C5 0.6(10) . . . . ?
C27 C23 C22 C30 0.0(7) . . . . ?
C27 C28 C29 C30 -0.1(11) . . . . ?
C34 C33 C31 C24 1.4(10) . . . . ?
C28 C29 C30 C22 2.1(11) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_sjx-20200616
_database_code_depnum_ccdc_archive 'CCDC 2019972'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Shen'
;Henan Normal University
China
;
_audit_update_record             
;
2020-09-02 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-09-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N O P'
_chemical_formula_sum            'C26 H24 N O P'
_chemical_formula_weight         397.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   17.9406(5)
_cell_length_b                   5.87332(13)
_cell_length_c                   22.2579(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.737(3)
_cell_angle_gamma                90
_cell_volume                     2178.57(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4487
_cell_measurement_temperature    295.76(11)
_cell_measurement_theta_max      71.4010
_cell_measurement_theta_min      4.1090
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10315
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.453
_diffrn_reflns_theta_min         4.114
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.76(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  33.00   1.00    1.00    --  -35.62  45.00 -31.00   86
  2  ω   -104.00 -18.00   1.00    1.00    --  -35.62 -45.00 178.00   86
  3  ω     18.00 104.00   1.00    1.00    --   35.62  45.00 -31.00   86
  4  ω     39.00 125.00   1.00    3.46    --  107.12 -45.00 178.00   86
  5  ω     90.00 176.00   1.00    3.46    --  107.12  45.00 -31.00   86
  6  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-150.00   51
  7  ω     22.00 102.00   1.00    1.00    --   35.62  57.00  90.00   80
  8  ω     21.00  96.00   1.00    1.00    --   35.62  57.00-180.00   75
  9  ω      4.00  31.00   1.00    1.00    --   35.62 -45.00 178.00   27
 10  ω     37.00 129.00   1.00    3.46    --  107.12 -30.00 150.00   92
 11  ω     40.00 113.00   1.00    3.46    --  107.12-111.00-150.00   73
 12  ω     56.00 105.00   1.00    3.46    --  107.12 -45.00  30.00   49
 13  ω     92.00 121.00   1.00    3.46    --  107.12 -45.00 -60.00   29
 14  ω     40.00  66.00   1.00    3.46    --  107.12 -45.00 -60.00   26
 15  ω    111.00 177.00   1.00    3.46    --  107.12 111.00-150.00   66
 16  ω     37.00  98.00   1.00    3.46    --  107.12-111.00-180.00   61
 17  ω    100.00 141.00   1.00    3.46    --  107.12 111.00-120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0574827000
_diffrn_orient_matrix_UB_12      0.0425301000
_diffrn_orient_matrix_UB_13      -0.0701673000
_diffrn_orient_matrix_UB_21      -0.0546981000
_diffrn_orient_matrix_UB_22      0.1424967000
_diffrn_orient_matrix_UB_23      0.0249039000
_diffrn_orient_matrix_UB_31      0.0473718000
_diffrn_orient_matrix_UB_32      0.2161823000
_diffrn_orient_matrix_UB_33      -0.0026045000
_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                3615
_reflns_number_total             4165
_reflns_odcompleteness_completeness 99.86
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.224
_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)+(0.0836P)²+1.2040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1547
_refine_ls_wR_factor_ref         0.1633
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C1AA) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C10A) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C16) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C10) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C12A) \\sim Ueq, Uanis(C1AB) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C0AB) \\sim Ueq, Uanis(C0AA) \\sim Ueq,
Uanis(C1A) \\sim Ueq, Uanis(C1AA) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Rigid body (RIGU) restrains
 C12A, C0AB, C1A, C10A, C11A, C1AB
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C10A, C11A, C1AB, C12A, C0AB, C1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10, C11, C1AA, C4, C12, C0AA, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(C10A)=1-FVAR(1)
 Sof(C10)=FVAR(1)
 Sof(C1AB)=Sof(H1AB)=Sof(C11A)=Sof(H11A)=Sof(C1A)=Sof(H1A)=Sof(C0AB)=Sof(H0AB)=
 1-FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C0AA)=Sof(H0AA)=Sof(C1AA)=Sof(H1AA)=Sof(C11)=Sof(H11)=
 FVAR(2)
 Fixed Sof: C12(0.65862) H12(0.65862) C12A(0.34138) H12A(0.34138)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C0AA(H0AA), C12(H12), C1AA(H1AA), C11(H11), C18(H18),
 C24(H24), C28(H28), C5(H5), C27(H27), C22(H22), C26(H26), C25(H25), C21(H21),
 C2(H2), C19(H19), C20(H20), C12A(H12A), C1AB(H1AB), C11A(H11A), C1A(H1A),
 C0AB(H0AB)
5.d Fitted hexagon refined as free rotating group:
 C10(C1,C0AA,C12,C1AA,C11), C12A(C1AB,C11A,C10A,C1A,C0AB)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
P9 P 0.73881(3) 0.58635(9) 0.27373(3) 0.03650(18) Uani 1 1 d . . . . .
O15 O 0.75566(10) 0.8280(3) 0.26300(9) 0.0503(4) Uani 1 1 d . . . . .
C7 C 0.80458(13) 0.4328(4) 0.18481(10) 0.0362(5) Uani 1 1 d . . . . .
H7 H 0.816323 0.595201 0.183286 0.043 Uiso 1 1 calc R U . . .
C8 C 0.80048(12) 0.3857(4) 0.25132(10) 0.0370(5) Uani 1 1 d . . . . .
H8A H 0.854422 0.389582 0.283766 0.044 Uiso 1 1 calc R U . . .
H8B H 0.779401 0.233536 0.251259 0.044 Uiso 1 1 calc R U . . .
C23 C 0.63444(13) 0.5156(4) 0.22969(11) 0.0383(5) Uani 1 1 d . . . . .
C4 C 0.87218(12) 0.3010(4) 0.17491(10) 0.0395(5) Uani 1 1 d . . . . .
C3 C 0.89521(14) 0.0849(4) 0.20012(13) 0.0475(6) Uani 1 1 d . . . . .
H3 H 0.869223 0.012873 0.224083 0.057 Uiso 1 1 calc R U . . .
C10 C 0.7576(3) 0.5268(7) 0.35695(14) 0.044(3) Uani 0.51(5) 1 d G U P A 1
C1 C 0.7573(3) 0.7117(6) 0.39585(18) 0.0816(16) Uani 0.661(4) 1 d G U P A 1
H1 H 0.748192 0.857593 0.378387 0.098 Uiso 0.661(4) 1 calc R U P A 1
C0AA C 0.7707(3) 0.6786(8) 0.46086(18) 0.116(2) Uani 0.661(4) 1 d G U P A 1
H0AA H 0.770499 0.802279 0.486891 0.139 Uiso 0.661(4) 1 calc R U P A 1
C12 C 0.7843(3) 0.4605(9) 0.48697(15) 0.115(3) Uani 0.6586 1 d G U P A 1
H12 H 0.793236 0.438362 0.530462 0.138 Uiso 0.6586 1 calc R U P A 1
C1AA C 0.7846(3) 0.2756(7) 0.4481(2) 0.126(3) Uani 0.661(4) 1 d G U P A 1
H1AA H 0.793667 0.129758 0.465530 0.151 Uiso 0.661(4) 1 calc R U P A 1
C11 C 0.7712(3) 0.3088(6) 0.3831(2) 0.0938(19) Uani 0.661(4) 1 d G U P A 1
H11 H 0.771361 0.185068 0.357026 0.113 Uiso 0.661(4) 1 calc R U P A 1
C18 C 0.68674(14) 0.1805(5) 0.12287(12) 0.0489(6) Uani 1 1 d . . . . .
H18 H 0.707776 0.070021 0.154599 0.059 Uiso 1 1 calc R U . . .
C24 C 0.58586(15) 0.6781(5) 0.18867(12) 0.0490(6) Uani 1 1 d . . . . .
H24 H 0.607188 0.819084 0.184680 0.059 Uiso 1 1 calc R U . . .
N1 N 0.99827(15) 0.0719(6) 0.15543(15) 0.0804(9) Uani 1 1 d . U . . .
C28 C 0.60162(15) 0.3063(4) 0.23535(13) 0.0511(6) Uani 1 1 d . . . . .
H28 H 0.633661 0.195420 0.262658 0.061 Uiso 1 1 calc R U . . .
C5 C 0.91287(15) 0.3962(5) 0.13953(13) 0.0562(7) Uani 1 1 d . . . . .
H5 H 0.898143 0.539396 0.121117 0.067 Uiso 1 1 calc R U . . .
C27 C 0.52124(16) 0.2623(5) 0.20040(15) 0.0594(7) Uani 1 1 d . . . . .
H27 H 0.499307 0.122593 0.204720 0.071 Uiso 1 1 calc R U . . .
C22 C 0.69516(18) 0.5447(5) 0.07959(13) 0.0584(7) Uani 1 1 d . . . . .
H22 H 0.721194 0.683136 0.081733 0.070 Uiso 1 1 calc R U . . .
C26 C 0.47396(16) 0.4241(6) 0.15948(15) 0.0650(8) Uani 1 1 d . . . . .
H26 H 0.420238 0.393081 0.135632 0.078 Uiso 1 1 calc R U . . .
C25 C 0.50590(17) 0.6326(6) 0.15360(14) 0.0624(7) Uani 1 1 d . . . . .
H25 H 0.473653 0.742492 0.126048 0.075 Uiso 1 1 calc R U . . .
C21 C 0.6240(2) 0.4966(7) 0.02715(14) 0.0745(8) Uani 1 1 d . . . . .
H21 H 0.603025 0.603851 -0.005539 0.089 Uiso 1 1 calc R U . . .
C2 C 0.95768(16) -0.0214(6) 0.18886(15) 0.0649(8) Uani 1 1 d . U . . .
H2 H 0.972318 -0.166822 0.205613 0.078 Uiso 1 1 calc R U . . .
C19 C 0.61594(16) 0.1366(6) 0.07106(14) 0.0649(8) Uani 1 1 d . . . . .
H19 H 0.589393 -0.001075 0.068728 0.078 Uiso 1 1 calc R U . . .
C20 C 0.58527(19) 0.2955(7) 0.02352(15) 0.0750(8) Uani 1 1 d . U . . .
H20 H 0.537923 0.265974 -0.011312 0.090 Uiso 1 1 calc R U . . .
C6 C 0.97590(18) 0.2802(8) 0.13103(17) 0.0774(9) Uani 1 1 d . U . . .
C16 C 1.0233(3) 0.3893(10) 0.0955(3) 0.1232(16) Uani 1 1 d . U . . .
H16A H 1.077586 0.412395 0.124784 0.185 Uiso 1 1 calc R U . . .
H16B H 0.999653 0.533323 0.078333 0.185 Uiso 1 1 calc R U . . .
H16C H 1.022908 0.291938 0.060772 0.185 Uiso 1 1 calc R U . . .
C12A C 0.7946(4) 0.4433(17) 0.4900(2) 0.097(4) Uani 0.3414 1 d G U P A 2
H12A H 0.806322 0.418516 0.533823 0.116 Uiso 0.3414 1 calc R U P A 2
C1AB C 0.8563(3) 0.4579(18) 0.4666(3) 0.098(3) Uani 0.339(4) 1 d G U P A 2
H1AB H 0.909343 0.442934 0.494767 0.118 Uiso 0.339(4) 1 calc R U P A 2
C11A C 0.8387(3) 0.4950(16) 0.4011(3) 0.082(3) Uani 0.339(4) 1 d G U P A 2
H11A H 0.880010 0.504810 0.385436 0.099 Uiso 0.339(4) 1 calc R U P A 2
C10A C 0.7594(3) 0.5175(13) 0.3590(2) 0.058(3) Uani 0.49(5) 1 d G U P A 2
C1A C 0.6977(3) 0.5028(14) 0.3824(3) 0.070(2) Uani 0.339(4) 1 d G U P A 2
H1A H 0.644634 0.517852 0.354214 0.084 Uiso 0.339(4) 1 calc R U P A 2
C0AB C 0.7153(4) 0.4658(15) 0.4479(3) 0.084(3) Uani 0.339(4) 1 d G U P A 2
H0AB H 0.673966 0.455976 0.463546 0.101 Uiso 0.339(4) 1 calc R U P A 2
C9 C 0.72640(13) 0.3843(4) 0.12820(10) 0.0390(5) 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
P9 O15 1.4886(16) . ?
P9 C8 1.809(2) . ?
P9 C23 1.811(2) . ?
P9 C10 1.790(3) . ?
P9 C10A 1.839(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(3) . ?
C7 C4 1.522(3) . ?
C7 C9 1.526(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C23 C24 1.384(3) . ?
C23 C28 1.389(3) . ?
C4 C3 1.388(3) . ?
C4 C5 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.384(4) . ?
C10 C1 1.3900 . ?
C10 C11 1.3900 . ?
C1 H1 0.9300 . ?
C1 C0AA 1.3900 . ?
C0AA H0AA 0.9300 . ?
C0AA C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C1AA 1.3900 . ?
C1AA H1AA 0.9300 . ?
C1AA C11 1.3900 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.388(4) . ?
C18 C9 1.375(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(4) . ?
N1 C2 1.336(5) . ?
N1 C6 1.338(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C27 H27 0.9300 . ?
C27 C26 1.371(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.404(4) . ?
C22 C9 1.387(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.379(4) . ?
C25 H25 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.357(5) . ?
C2 H2 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.364(5) . ?
C20 H20 0.9300 . ?
C6 C16 1.502(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12A H12A 0.9300 . ?
C12A C1AB 1.3900 . ?
C12A C0AB 1.3900 . ?
C1AB H1AB 0.9300 . ?
C1AB C11A 1.3900 . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3900 . ?
C10A C1A 1.3900 . ?
C1A H1A 0.9300 . ?
C1A C0AB 1.3900 . ?
C0AB H0AB 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
O15 P9 C8 113.32(10) . . ?
O15 P9 C23 111.25(10) . . ?
O15 P9 C10 112.38(15) . . ?
O15 P9 C10A 113.6(2) . . ?
C8 P9 C23 108.46(10) . . ?
C8 P9 C10A 103.4(2) . . ?
C23 P9 C10A 106.29(19) . . ?
C10 P9 C8 104.97(14) . . ?
C10 P9 C23 106.00(16) . . ?
C8 C7 H7 107.3 . . ?
C4 C7 H7 107.3 . . ?
C4 C7 C8 111.92(18) . . ?
C4 C7 C9 108.87(17) . . ?
C9 C7 H7 107.3 . . ?
C9 C7 C8 113.91(17) . . ?
P9 C8 H8A 108.8 . . ?
P9 C8 H8B 108.8 . . ?
C7 C8 P9 113.66(15) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C24 C23 P9 118.11(18) . . ?
C24 C23 C28 119.1(2) . . ?
C28 C23 P9 122.82(18) . . ?
C3 C4 C7 122.7(2) . . ?
C5 C4 C7 119.8(2) . . ?
C5 C4 C3 117.5(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3 120.7 . . ?
C1 C10 P9 116.7(2) . . ?
C1 C10 C11 120.0 . . ?
C11 C10 P9 123.3(2) . . ?
C10 C1 H1 120.0 . . ?
C10 C1 C0AA 120.0 . . ?
C0AA C1 H1 120.0 . . ?
C1 C0AA H0AA 120.0 . . ?
C12 C0AA C1 120.0 . . ?
C12 C0AA H0AA 120.0 . . ?
C0AA C12 H12 120.0 . . ?
C1AA C12 C0AA 120.0 . . ?
C1AA C12 H12 120.0 . . ?
C12 C1AA H1AA 120.0 . . ?
C12 C1AA C11 120.0 . . ?
C11 C1AA H1AA 120.0 . . ?
C10 C11 H11 120.0 . . ?
C1AA C11 C10 120.0 . . ?
C1AA C11 H11 120.0 . . ?
C19 C18 H18 119.4 . . ?
C9 C18 H18 119.4 . . ?
C9 C18 C19 121.3(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C2 N1 C6 117.2(3) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.1(3) . . ?
C27 C28 H28 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C28 C27 H27 119.9 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C21 C22 H22 120.3 . . ?
C9 C22 H22 120.3 . . ?
C9 C22 C21 119.5(3) . . ?
C27 C26 H26 119.9 . . ?
C27 C26 C25 120.1(3) . . ?
C25 C26 H26 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C3 C2 H2 118.0 . . ?
N1 C2 C3 124.1(3) . . ?
N1 C2 H2 118.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 C16 117.4(3) . . ?
C5 C6 C16 120.6(4) . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1AB C12A H12A 120.0 . . ?
C1AB C12A C0AB 120.0 . . ?
C0AB C12A H12A 120.0 . . ?
C12A C1AB H1AB 120.0 . . ?
C11A C1AB C12A 120.0 . . ?
C11A C1AB H1AB 120.0 . . ?
C1AB C11A H11A 120.0 . . ?
C1AB C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A P9 118.7(3) . . ?
C1A C10A P9 121.1(3) . . ?
C1A C10A C11A 120.0 . . ?
C10A C1A H1A 120.0 . . ?
C10A C1A C0AB 120.0 . . ?
C0AB C1A H1A 120.0 . . ?
C12A C0AB H0AB 120.0 . . ?
C1A C0AB C12A 120.0 . . ?
C1A C0AB H0AB 120.0 . . ?
C18 C9 C7 121.5(2) . . ?
C18 C9 C22 118.5(2) . . ?
C22 C9 C7 120.0(2) . . ?

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
P9 C23 C24 C25 179.6(2) . . . . ?
P9 C23 C28 C27 179.9(2) . . . . ?
P9 C10 C1 C0AA 179.4(3) . . . . ?
P9 C10 C11 C1AA -179.4(4) . . . . ?
P9 C10A C1A C0AB -175.7(6) . . . . ?
O15 P9 C8 C7 -47.26(18) . . . . ?
O15 P9 C23 C24 5.3(2) . . . . ?
O15 P9 C23 C28 -174.87(19) . . . . ?
O15 P9 C10 C1 21.6(3) . . . . ?
O15 P9 C10 C11 -159.0(2) . . . . ?
O15 P9 C10A C11A -74.7(4) . . . . ?
O15 P9 C10A C1A 101.0(4) . . . . ?
C7 C4 C3 C2 -179.7(2) . . . . ?
C7 C4 C5 C6 178.7(3) . . . . ?
C8 P9 C23 C24 -120.02(19) . . . . ?
C8 P9 C23 C28 59.9(2) . . . . ?
C8 P9 C10 C1 145.2(2) . . . . ?
C8 P9 C10 C11 -35.4(3) . . . . ?
C8 P9 C10A C11A 48.5(4) . . . . ?
C8 P9 C10A C1A -135.8(4) . . . . ?
C8 C7 C4 C3 34.4(3) . . . . ?
C8 C7 C4 C5 -145.8(2) . . . . ?
C8 C7 C9 C18 -50.7(3) . . . . ?
C8 C7 C9 C22 131.3(2) . . . . ?
C23 P9 C8 C7 76.80(17) . . . . ?
C23 P9 C10 C1 -100.1(2) . . . . ?
C23 P9 C10 C11 79.2(3) . . . . ?
C23 P9 C10A C11A 162.6(4) . . . . ?
C23 P9 C10A C1A -21.7(5) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C23 C28 C27 C26 0.8(4) . . . . ?
C4 C7 C8 P9 165.65(14) . . . . ?
C4 C7 C9 C18 75.0(3) . . . . ?
C4 C7 C9 C22 -103.0(2) . . . . ?
C4 C3 C2 N1 0.6(4) . . . . ?
C4 C5 C6 N1 1.4(5) . . . . ?
C4 C5 C6 C16 -176.6(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C10 P9 C8 C7 -170.24(19) . . . . ?
C10 P9 C23 C24 127.7(2) . . . . ?
C10 P9 C23 C28 -52.4(2) . . . . ?
C10 C1 C0AA C12 0.0 . . . . ?
C1 C10 C11 C1AA 0.0 . . . . ?
C1 C0AA C12 C1AA 0.0 . . . . ?
C0AA C12 C1AA C11 0.0 . . . . ?
C12 C1AA C11 C10 0.0 . . . . ?
C11 C10 C1 C0AA 0.0 . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C24 C23 C28 C27 -0.2(4) . . . . ?
C28 C23 C24 C25 -0.3(4) . . . . ?
C28 C27 C26 C25 -0.9(4) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C27 C26 C25 C24 0.5(5) . . . . ?
C22 C21 C20 C19 -0.5(5) . . . . ?
C21 C22 C9 C7 178.9(2) . . . . ?
C21 C22 C9 C18 0.8(4) . . . . ?
C2 N1 C6 C5 -0.3(5) . . . . ?
C2 N1 C6 C16 177.8(4) . . . . ?
C19 C18 C9 C7 -179.6(2) . . . . ?
C19 C18 C9 C22 -1.6(4) . . . . ?
C6 N1 C2 C3 -0.7(5) . . . . ?
C12A C1AB C11A C10A 0.0 . . . . ?
C1AB C12A C0AB C1A 0.0 . . . . ?
C1AB C11A C10A P9 175.8(6) . . . . ?
C1AB C11A C10A C1A 0.0 . . . . ?
C11A C10A C1A C0AB 0.0 . . . . ?
C10A P9 C8 C7 -170.7(2) . . . . ?
C10A P9 C23 C24 129.4(3) . . . . ?
C10A P9 C23 C28 -50.7(3) . . . . ?
C10A C1A C0AB C12A 0.0 . . . . ?
C0AB C12A C1AB C11A 0.0 . . . . ?
C9 C7 C8 P9 -70.3(2) . . . . ?
C9 C7 C4 C3 -92.4(2) . . . . ?
C9 C7 C4 C5 87.4(3) . . . . ?
C9 C18 C19 C20 1.3(4) . . . . ?
C9 C22 C21 C20 0.2(5) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2020-06-16
_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 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.420
####################################################################### 
# 
# 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_sjx-20200612
_database_code_depnum_ccdc_archive 'CCDC 2019970'
loop_
_audit_author_name
_audit_author_address
'jiaxuan shen'
;Henan Normal University
China
;
_audit_update_record             
;
2020-07-29 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_audit_creation_date             2020-06-13
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'diphenyl(1-(pyridin-4-yl)-2,3-dihydro-1H-inden-2-yl)phosphine oxide'
_chemical_formula_moiety         'C26 H22 N O P'
_chemical_formula_sum            'C26 H22 N O P'
_chemical_formula_weight         395.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   9.48540(10)
_cell_length_b                   20.0552(3)
_cell_length_c                   11.4108(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.2540(10)
_cell_angle_gamma                90
_cell_volume                     2121.24(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5988
_cell_measurement_temperature    295.38(10)
_cell_measurement_theta_max      71.0800
_cell_measurement_theta_min      4.5250
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10671
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.420
_diffrn_reflns_theta_min         4.409
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.38(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  21.00   1.00    1.00    --  -35.62  98.00-101.00   95
  2  ω      0.00  74.00   1.00    1.00    --   35.62 -98.00 151.00   74
  3  ω     37.00 111.00   1.00    2.36    --  107.12 -98.00 151.00   74
  4  ω    100.00 177.00   1.00    2.36    --  107.12  98.00-101.00   77
  5  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -60.00   84
  6  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00  60.00   84
  7  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 -60.00   51
  8  ω     58.00  90.00   1.00    1.00    --   35.62 178.00-120.00   32
  9  ω     64.00 108.00   1.00    1.00    --   35.62 178.00 150.00   44
 10  ω    115.00 176.00   1.00    2.36    --  107.12  45.00  60.00   61
 11  ω     44.00 109.00   1.00    2.36    --  107.12 -95.00-180.00   65
 12  ω     44.00  73.00   1.00    2.36    --  107.12 -45.00 150.00   29
 13  ω     37.00 126.00   1.00    2.36    --  107.12 -30.00 -30.00   89
 14  ω    133.00 177.00   1.00    2.36    --  107.12 111.00-150.00   44
 15  ω     67.00 111.00   1.00    2.36    --  107.12-111.00 -60.00   44
 16  ω     41.00  86.00   1.00    2.36    --  107.12 -77.00 -90.00   45
 17  ω    101.00 134.00   1.00    2.36    --  107.12 -77.00 -90.00   33
 18  ω     76.00 103.00   1.00    2.36    --  107.12 -45.00 150.00   27
 19  ω     97.00 125.00   1.00    2.36    --  107.12 -61.00 -60.00   28
 20  ω     41.00  81.00   1.00    2.36    --  107.12 -61.00 -60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0825134000
_diffrn_orient_matrix_UB_12      0.0655160000
_diffrn_orient_matrix_UB_13      0.0078795000
_diffrn_orient_matrix_UB_21      0.1368827000
_diffrn_orient_matrix_UB_22      0.0308608000
_diffrn_orient_matrix_UB_23      0.0781996000
_diffrn_orient_matrix_UB_31      0.0454778000
_diffrn_orient_matrix_UB_32      0.0257109000
_diffrn_orient_matrix_UB_33      -0.1136036000
_diffrn_oxdiff_digest_frames     
;
01d11aecd6d41e325bb0533b98b0b903770116863fa
;
_diffrn_oxdiff_digest_hkl        
;
0180304dc16609756acac1cc6ff406780a8d58
;
_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                3461
_reflns_number_total             4041
_reflns_odcompleteness_completeness 99.85
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.072
_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)+(0.0681P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1154
_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 Ternary CH refined with riding coordinates:
 C9(H9), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C29(H29), C19(H19), C23(H23), C7(H7), C28(H28), C4(H4), C26(H26),
 C6(H6), C14(H14), C5(H5), C27(H27), C22(H22), C16(H16), C21(H21), C20(H20),
 C13(H13), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
P10 P 0.50612(4) 0.76843(2) 0.78695(3) 0.03484(13) Uani 1 1 d . . . . .
O11 O 0.51675(13) 0.76110(6) 0.91863(10) 0.0479(3) Uani 1 1 d . . . . .
C8 C 0.60448(16) 0.58052(8) 0.78980(13) 0.0373(3) Uani 1 1 d . . . . .
C9 C 0.48454(15) 0.63132(8) 0.75476(13) 0.0367(3) Uani 1 1 d . . . . .
H9 H 0.445928 0.642033 0.825653 0.044 Uiso 1 1 calc R . . . .
C24 C 0.61725(16) 0.83603(8) 0.75450(13) 0.0366(3) Uani 1 1 d . . . . .
C18 C 0.32287(17) 0.78448(8) 0.70802(13) 0.0371(3) Uani 1 1 d . . . . .
C15 C 0.36206(17) 0.60798(8) 0.65602(15) 0.0431(4) Uani 1 1 d . . . . .
C1 C 0.56540(16) 0.69415(8) 0.72004(13) 0.0367(3) Uani 1 1 d . . . . .
H1 H 0.545203 0.698973 0.632602 0.044 Uiso 1 1 calc R . . . .
C3 C 0.73969(17) 0.60829(9) 0.79618(14) 0.0409(4) Uani 1 1 d . . . . .
C25 C 0.63142(18) 0.85198(9) 0.63917(14) 0.0447(4) Uani 1 1 d . . . . .
H25 H 0.582751 0.827174 0.574202 0.054 Uiso 1 1 calc R . . . .
N12 N 0.1336(2) 0.56558(11) 0.47141(19) 0.0772(6) Uani 1 1 d . . . . .
C29 C 0.69207(18) 0.87329(9) 0.85079(15) 0.0472(4) Uani 1 1 d . . . . .
H29 H 0.683191 0.863031 0.928375 0.057 Uiso 1 1 calc R . . . .
C19 C 0.27838(19) 0.77988(10) 0.58389(14) 0.0468(4) Uani 1 1 d . . . . .
H19 H 0.344349 0.768777 0.537308 0.056 Uiso 1 1 calc R . . . .
C23 C 0.22262(19) 0.80209(9) 0.77589(15) 0.0479(4) Uani 1 1 d . . . . .
H23 H 0.251390 0.805748 0.858777 0.058 Uiso 1 1 calc R . . . .
C7 C 0.59025(19) 0.51408(9) 0.81885(16) 0.0487(4) Uani 1 1 d . . . . .
H7 H 0.499357 0.495532 0.814159 0.058 Uiso 1 1 calc R . . . .
C2 C 0.72891(17) 0.68149(9) 0.76740(18) 0.0496(4) Uani 1 1 d . . . . .
H2A H 0.783004 0.692463 0.706779 0.060 Uiso 1 1 calc R . . . .
H2B H 0.765468 0.707936 0.838544 0.060 Uiso 1 1 calc R . . . .
C28 C 0.77938(19) 0.92541(10) 0.83146(18) 0.0550(5) Uani 1 1 d . . . . .
H28 H 0.830416 0.949825 0.895991 0.066 Uiso 1 1 calc R . . . .
C4 C 0.86229(19) 0.56945(10) 0.83181(16) 0.0517(4) Uani 1 1 d . . . . .
H4 H 0.953296 0.587775 0.836021 0.062 Uiso 1 1 calc R . . . .
C26 C 0.7180(2) 0.90477(10) 0.62109(17) 0.0532(4) Uani 1 1 d . . . . .
H26 H 0.726849 0.915638 0.543756 0.064 Uiso 1 1 calc R . . . .
C6 C 0.7133(2) 0.47566(10) 0.85497(17) 0.0558(5) Uani 1 1 d . . . . .
H6 H 0.705071 0.431126 0.875219 0.067 Uiso 1 1 calc R . . . .
C14 C 0.3860(2) 0.57831(11) 0.55255(15) 0.0546(5) Uani 1 1 d . . . . .
H14 H 0.479723 0.571784 0.542351 0.066 Uiso 1 1 calc R . . . .
C5 C 0.8480(2) 0.50318(10) 0.86103(17) 0.0562(5) Uani 1 1 d . . . . .
H5 H 0.929919 0.476957 0.884962 0.067 Uiso 1 1 calc R . . . .
C27 C 0.79069(19) 0.94116(10) 0.7165(2) 0.0563(5) Uani 1 1 d . . . . .
H27 H 0.848191 0.976794 0.703445 0.068 Uiso 1 1 calc R . . . .
C22 C 0.0812(2) 0.81411(12) 0.72083(19) 0.0628(5) Uani 1 1 d . . . . .
H22 H 0.014990 0.825991 0.766724 0.075 Uiso 1 1 calc R . . . .
C16 C 0.2194(2) 0.61539(11) 0.6643(2) 0.0623(5) Uani 1 1 d . . . . .
H16 H 0.196191 0.634360 0.732195 0.075 Uiso 1 1 calc R . . . .
C21 C 0.0374(2) 0.80869(12) 0.5988(2) 0.0665(6) Uani 1 1 d . . . . .
H21 H -0.058568 0.816309 0.562190 0.080 Uiso 1 1 calc R . . . .
C20 C 0.1361(2) 0.79185(12) 0.53028(17) 0.0603(5) Uani 1 1 d . . . . .
H20 H 0.106304 0.788571 0.447411 0.072 Uiso 1 1 calc R . . . .
C13 C 0.2701(3) 0.55840(12) 0.46439(18) 0.0683(6) Uani 1 1 d . . . . .
H13 H 0.289424 0.538691 0.395705 0.082 Uiso 1 1 calc R . . . .
C17 C 0.1115(2) 0.59404(13) 0.5697(3) 0.0786(7) Uani 1 1 d . . . . .
H17 H 0.016438 0.600344 0.576399 0.094 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P10 O11 1.4917(11) . ?
P10 C24 1.8032(16) . ?
P10 C18 1.8087(16) . ?
P10 C1 1.8167(16) . ?
C8 C9 1.516(2) . ?
C8 C3 1.386(2) . ?
C8 C7 1.387(2) . ?
C9 H9 0.9800 . ?
C9 C15 1.511(2) . ?
C9 C1 1.569(2) . ?
C24 C25 1.388(2) . ?
C24 C29 1.392(2) . ?
C18 C19 1.392(2) . ?
C18 C23 1.393(2) . ?
C15 C14 1.383(3) . ?
C15 C16 1.385(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.551(2) . ?
C3 C2 1.503(2) . ?
C3 C4 1.387(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(2) . ?
N12 C13 1.322(3) . ?
N12 C17 1.314(3) . ?
C29 H29 0.9300 . ?
C29 C28 1.380(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C28 H28 0.9300 . ?
C28 C27 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.369(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C5 H5 0.9300 . ?
C27 H27 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.370(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.384(3) . ?
C20 H20 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17 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
O11 P10 C24 111.31(7) . . ?
O11 P10 C18 111.81(7) . . ?
O11 P10 C1 112.44(7) . . ?
C24 P10 C18 107.81(7) . . ?
C24 P10 C1 106.48(7) . . ?
C18 P10 C1 106.69(7) . . ?
C3 C8 C9 112.22(14) . . ?
C3 C8 C7 120.64(15) . . ?
C7 C8 C9 127.09(15) . . ?
C8 C9 H9 108.7 . . ?
C8 C9 C1 103.09(12) . . ?
C15 C9 C8 113.81(13) . . ?
C15 C9 H9 108.7 . . ?
C15 C9 C1 113.59(12) . . ?
C1 C9 H9 108.7 . . ?
C25 C24 P10 123.11(12) . . ?
C25 C24 C29 119.25(16) . . ?
C29 C24 P10 117.64(12) . . ?
C19 C18 P10 123.13(12) . . ?
C19 C18 C23 119.13(15) . . ?
C23 C18 P10 117.74(12) . . ?
C14 C15 C9 122.02(15) . . ?
C14 C15 C16 116.40(17) . . ?
C16 C15 C9 121.58(17) . . ?
P10 C1 H1 109.6 . . ?
C9 C1 P10 109.93(10) . . ?
C9 C1 H1 109.6 . . ?
C2 C1 P10 111.32(11) . . ?
C2 C1 C9 106.67(12) . . ?
C2 C1 H1 109.6 . . ?
C8 C3 C2 111.21(14) . . ?
C8 C3 C4 119.91(17) . . ?
C4 C3 C2 128.79(16) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.88(16) . . ?
C26 C25 H25 120.1 . . ?
C17 N12 C13 115.74(19) . . ?
C24 C29 H29 119.9 . . ?
C28 C29 C24 120.21(16) . . ?
C28 C29 H29 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.76(16) . . ?
C20 C19 H19 120.1 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.31(17) . . ?
C22 C23 H23 119.8 . . ?
C8 C7 H7 120.4 . . ?
C6 C7 C8 119.11(17) . . ?
C6 C7 H7 120.4 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 C1 104.63(13) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C29 C28 H28 120.1 . . ?
C27 C28 C29 119.81(17) . . ?
C27 C28 H28 120.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.41(17) . . ?
C5 C4 H4 120.3 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.31(17) . . ?
C27 C26 H26 119.8 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.32(18) . . ?
C5 C6 H6 119.8 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.75(19) . . ?
C13 C14 H14 120.1 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(17) . . ?
C6 C5 H5 119.7 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.52(17) . . ?
C26 C27 H27 119.7 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.40(17) . . ?
C21 C22 H22 119.8 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(2) . . ?
C17 C16 H16 120.6 . . ?
C22 C21 H21 120.1 . . ?
C22 C21 C20 119.88(18) . . ?
C20 C21 H21 120.1 . . ?
C19 C20 C21 120.50(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
N12 C13 C14 124.2(2) . . ?
N12 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
N12 C17 C16 125.0(2) . . ?
N12 C17 H17 117.5 . . ?
C16 C17 H17 117.5 . . ?

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
P10 C24 C25 C26 179.62(14) . . . . ?
P10 C24 C29 C28 179.67(14) . . . . ?
P10 C18 C19 C20 178.97(16) . . . . ?
P10 C18 C23 C22 -179.22(16) . . . . ?
P10 C1 C2 C3 134.35(12) . . . . ?
O11 P10 C24 C25 177.47(13) . . . . ?
O11 P10 C24 C29 -2.27(15) . . . . ?
O11 P10 C18 C19 -166.52(14) . . . . ?
O11 P10 C18 C23 13.33(16) . . . . ?
O11 P10 C1 C9 52.30(12) . . . . ?
O11 P10 C1 C2 -65.67(13) . . . . ?
C8 C9 C15 C14 -47.1(2) . . . . ?
C8 C9 C15 C16 133.07(18) . . . . ?
C8 C9 C1 P10 -134.76(10) . . . . ?
C8 C9 C1 C2 -13.95(16) . . . . ?
C8 C3 C2 C1 -9.54(19) . . . . ?
C8 C3 C4 C5 -0.2(3) . . . . ?
C8 C7 C6 C5 -0.5(3) . . . . ?
C9 C8 C3 C2 0.51(19) . . . . ?
C9 C8 C3 C4 177.40(15) . . . . ?
C9 C8 C7 C6 -176.65(16) . . . . ?
C9 C15 C14 C13 -179.39(18) . . . . ?
C9 C15 C16 C17 178.86(19) . . . . ?
C9 C1 C2 C3 14.42(17) . . . . ?
C24 P10 C18 C19 70.82(16) . . . . ?
C24 P10 C18 C23 -109.32(14) . . . . ?
C24 P10 C1 C9 174.44(10) . . . . ?
C24 P10 C1 C2 56.48(12) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
C24 C29 C28 C27 1.0(3) . . . . ?
C18 P10 C24 C25 -59.57(15) . . . . ?
C18 P10 C24 C29 120.70(13) . . . . ?
C18 P10 C1 C9 -70.62(11) . . . . ?
C18 P10 C1 C2 171.41(11) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C18 C23 C22 C21 0.2(3) . . . . ?
C15 C9 C1 P10 101.61(13) . . . . ?
C15 C9 C1 C2 -137.58(14) . . . . ?
C15 C14 C13 N12 -0.1(3) . . . . ?
C15 C16 C17 N12 1.3(4) . . . . ?
C1 P10 C24 C25 54.61(15) . . . . ?
C1 P10 C24 C29 -125.13(13) . . . . ?
C1 P10 C18 C19 -43.21(16) . . . . ?
C1 P10 C18 C23 136.64(14) . . . . ?
C1 C9 C15 C14 70.5(2) . . . . ?
C1 C9 C15 C16 -109.36(18) . . . . ?
C3 C8 C9 C15 132.07(14) . . . . ?
C3 C8 C9 C1 8.59(17) . . . . ?
C3 C8 C7 C6 0.3(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C25 C24 C29 C28 -0.1(3) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C29 C24 C25 C26 -0.6(3) . . . . ?
C29 C28 C27 C26 -1.2(3) . . . . ?
C19 C18 C23 C22 0.6(3) . . . . ?
C23 C18 C19 C20 -0.9(3) . . . . ?
C23 C22 C21 C20 -0.8(4) . . . . ?
C7 C8 C9 C15 -50.8(2) . . . . ?
C7 C8 C9 C1 -174.27(15) . . . . ?
C7 C8 C3 C2 -176.84(15) . . . . ?
C7 C8 C3 C4 0.1(2) . . . . ?
C7 C6 C5 C4 0.3(3) . . . . ?
C2 C3 C4 C5 176.09(17) . . . . ?
C4 C3 C2 C1 173.92(16) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C22 C21 C20 C19 0.6(4) . . . . ?
C16 C15 C14 C13 0.4(3) . . . . ?
C13 N12 C17 C16 -1.0(4) . . . . ?
C17 N12 C13 C14 0.4(4) . . . . ?

_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 1.184
_oxdiff_exptl_absorpt_empirical_full_min 0.842
