# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_niuy1_0706
_database_code_depnum_ccdc_archive 'CCDC 2043001'
loop_
_audit_author_name
_audit_author_address
niuuuu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 Cl N O P'
_chemical_formula_sum            'C23 H29 Cl N O P'
_chemical_formula_weight         401.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3409(3)
_cell_length_b                   15.6455(3)
_cell_length_c                   19.8457(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4452.76(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3759
_cell_measurement_temperature    230(17)
_cell_measurement_theta_max      69.7970
_cell_measurement_theta_min      8.6560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9938
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         4.456
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 122.00   1.00    1.50    --  108.00 -12.00  60.00   86
  2  ω     45.00  75.00   1.00    1.00    --   54.00 -57.00 120.00   30
  3  ω     16.00 127.00   1.00    1.00    --   54.00  19.00  90.00  111
  4  ω    101.00 165.00   1.00    1.50    --  108.00 111.00  60.00   64
  5  ω    123.00 149.00   1.00    1.50    --  108.00 111.00-120.00   26
  6  ω     82.00 170.00   1.00    1.50    --  108.00  38.00-120.00   88
  7  ω     63.00 115.00   1.00    1.50    --  108.00 -77.00-120.00   52
  8  ω     44.00  84.00   1.00    1.00    --   54.00-125.00-120.00   40
  9  ω      3.00  66.00   1.00    1.00    --    0.00  57.00-180.00   63
 10  ω    -17.00  25.00   1.00    1.00    --    0.00  57.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0074054000
_diffrn_orient_matrix_UB_12      -0.0958672000
_diffrn_orient_matrix_UB_13      0.0169483000
_diffrn_orient_matrix_UB_21      -0.0477229000
_diffrn_orient_matrix_UB_22      -0.0164279000
_diffrn_orient_matrix_UB_23      -0.0683086000
_diffrn_orient_matrix_UB_31      0.0959709000
_diffrn_orient_matrix_UB_32      -0.0155400000
_diffrn_orient_matrix_UB_33      -0.0326721000
_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                3271
_reflns_number_total             3936
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.044
_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)+(0.0835P)²+1.5918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C11(H11), C13(H13), C15(H15), C16(H16), C17(H17), C20(H20)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.07986(4) 0.24268(3) 0.31611(3) 0.03842(19) Uani 1 1 d . . . . .
Cl2 Cl 0.23010(11) -0.03173(6) 0.57268(5) 0.1156(5) Uani 1 1 d . . . . .
O3 O 0.11509(11) 0.16848(9) 0.35528(8) 0.0482(4) Uani 1 1 d . . . . .
C4 C 0.16207(15) 0.33109(13) 0.31504(11) 0.0397(5) Uani 1 1 d . . . . .
C5 C 0.23894(14) 0.33887(12) 0.35949(10) 0.0353(4) Uani 1 1 d . . . . .
C6 C 0.27701(17) 0.47960(14) 0.30784(12) 0.0474(5) Uani 1 1 d . . . . .
H6 H 0.314572 0.527998 0.305978 0.057 Uiso 1 1 calc R U . . .
C7 C 0.28019(15) 0.29098(13) 0.41444(11) 0.0384(5) Uani 1 1 d . . . . .
N8 N 0.36379(13) 0.41202(11) 0.40051(10) 0.0467(5) Uani 1 1 d . . . . .
C9 C 0.20904(19) 0.20813(16) 0.50854(13) 0.0554(6) Uani 1 1 d . . . . .
H9 H 0.181075 0.258301 0.523473 0.066 Uiso 1 1 calc R U . . .
C10 C 0.25973(15) 0.20862(13) 0.44904(11) 0.0397(5) Uani 1 1 d . . . . .
C11 C 0.20234(19) 0.47016(15) 0.26567(14) 0.0571(6) Uani 1 1 d . . . . .
H11 H 0.188679 0.512545 0.234339 0.069 Uiso 1 1 calc R U . . .
C12 C 0.29481(15) 0.41443(12) 0.35351(11) 0.0390(5) Uani 1 1 d . . . . .
C13 C 0.30040(19) 0.13315(15) 0.42833(12) 0.0489(6) Uani 1 1 d . . . . .
H13 H 0.334300 0.132023 0.388397 0.059 Uiso 1 1 calc R U . . .
C14 C 0.06251(18) 0.20583(15) 0.22701(13) 0.0513(6) Uani 1 1 d . . . . .
C15 C 0.35383(17) 0.33837(14) 0.43634(12) 0.0470(5) Uani 1 1 d . . . . .
H15 H 0.392759 0.322321 0.471619 0.056 Uiso 1 1 calc R U . . .
C16 C 0.14646(19) 0.39722(15) 0.26940(13) 0.0547(6) Uani 1 1 d . . . . .
H16 H 0.096293 0.392556 0.239925 0.066 Uiso 1 1 calc R U . . .
C17 C 0.2916(2) 0.05879(15) 0.46610(14) 0.0596(7) Uani 1 1 d . . . . .
H17 H 0.319622 0.008336 0.451822 0.071 Uiso 1 1 calc R U . . .
C18 C -0.02745(18) 0.28512(17) 0.35624(15) 0.0601(7) Uani 1 1 d . . . . .
C19 C 0.0047(3) 0.2615(2) 0.17920(16) 0.0806(10) Uani 1 1 d . . . . .
H19A H -0.057049 0.268394 0.197140 0.121 Uiso 1 1 calc R U . . .
H19B H 0.001125 0.234466 0.135843 0.121 Uiso 1 1 calc R U . . .
H19C H 0.033652 0.316496 0.174643 0.121 Uiso 1 1 calc R U . . .
C20 C 0.1994(2) 0.13390(18) 0.54609(14) 0.0680(8) Uani 1 1 d . . . . .
H20 H 0.164747 0.134116 0.585679 0.082 Uiso 1 1 calc R U . . .
C21 C 0.0158(2) 0.11722(18) 0.22968(18) 0.0768(9) Uani 1 1 d . . . . .
H21A H 0.049849 0.080896 0.259936 0.115 Uiso 1 1 calc R U . . .
H21B H 0.015704 0.092400 0.185445 0.115 Uiso 1 1 calc R U . . .
H21C H -0.047191 0.123149 0.245335 0.115 Uiso 1 1 calc R U . . .
C22 C 0.2411(2) 0.06085(17) 0.52458(13) 0.0639(8) Uani 1 1 d . . . . .
C23 C 0.1606(2) 0.1948(2) 0.19820(16) 0.0741(8) Uani 1 1 d . . . . .
H23A H 0.189195 0.249876 0.192938 0.111 Uiso 1 1 calc R U . . .
H23B H 0.156860 0.167020 0.155159 0.111 Uiso 1 1 calc R U . . .
H23C H 0.197225 0.160642 0.228397 0.111 Uiso 1 1 calc R U . . .
C24 C 0.4365(2) 0.47547(16) 0.41007(16) 0.0639(7) Uani 1 1 d . . . . .
H24A H 0.479763 0.472647 0.373236 0.096 Uiso 1 1 calc R U . . .
H24B H 0.468691 0.464323 0.451548 0.096 Uiso 1 1 calc R U . . .
H24C H 0.409025 0.531393 0.411734 0.096 Uiso 1 1 calc R U . . .
C25 C 0.0024(3) 0.3084(3) 0.42832(18) 0.0923(11) Uani 1 1 d . . . . .
H25A H 0.025312 0.258310 0.450768 0.138 Uiso 1 1 calc R U . . .
H25B H -0.050234 0.330696 0.452543 0.138 Uiso 1 1 calc R U . . .
H25C H 0.050688 0.350861 0.426684 0.138 Uiso 1 1 calc R U . . .
C1 C -0.0980(2) 0.2123(2) 0.3616(2) 0.0933(12) Uani 1 1 d . . . . .
H1A H -0.120904 0.198257 0.317551 0.140 Uiso 1 1 calc R U . . .
H1B H -0.149056 0.229782 0.389720 0.140 Uiso 1 1 calc R U . . .
H1C H -0.068374 0.163079 0.381032 0.140 Uiso 1 1 calc R U . . .
C2 C -0.0716(3) 0.3629(3) 0.3229(2) 0.1199(18) Uani 1 1 d . . . . .
H2A H -0.027129 0.408728 0.321330 0.180 Uiso 1 1 calc R U . . .
H2B H -0.125158 0.380609 0.348360 0.180 Uiso 1 1 calc R U . . .
H2C H -0.090474 0.348498 0.277855 0.180 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.4855(15) . ?
P1 C4 1.818(2) . ?
P1 C14 1.876(3) . ?
P1 C18 1.856(3) . ?
Cl2 C22 1.742(2) . ?
C4 C5 1.417(3) . ?
C4 C16 1.393(3) . ?
C5 C7 1.449(3) . ?
C5 C12 1.433(3) . ?
C6 H6 0.9300 . ?
C6 C11 1.367(4) . ?
C6 C12 1.388(3) . ?
C7 C10 1.489(3) . ?
C7 C15 1.362(3) . ?
N8 C12 1.360(3) . ?
N8 C15 1.361(3) . ?
N8 C24 1.452(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C20 1.387(4) . ?
C10 C13 1.379(3) . ?
C11 H11 0.9300 . ?
C11 C16 1.396(3) . ?
C13 H13 0.9300 . ?
C13 C17 1.390(3) . ?
C14 C19 1.532(4) . ?
C14 C21 1.540(3) . ?
C14 C23 1.528(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C17 C22 1.368(4) . ?
C18 C25 1.537(5) . ?
C18 C1 1.528(4) . ?
C18 C2 1.524(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C22 1.359(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
O3 P1 C4 112.34(9) . . ?
O3 P1 C14 107.34(10) . . ?
O3 P1 C18 109.71(11) . . ?
C4 P1 C14 107.99(10) . . ?
C4 P1 C18 105.70(11) . . ?
C18 P1 C14 113.85(13) . . ?
C5 C4 P1 124.24(15) . . ?
C16 C4 P1 117.94(17) . . ?
C16 C4 C5 117.77(19) . . ?
C4 C5 C7 137.85(18) . . ?
C4 C5 C12 117.01(18) . . ?
C12 C5 C7 105.11(18) . . ?
C11 C6 H6 121.2 . . ?
C11 C6 C12 117.7(2) . . ?
C12 C6 H6 121.2 . . ?
C5 C7 C10 135.54(19) . . ?
C15 C7 C5 105.97(18) . . ?
C15 C7 C10 118.5(2) . . ?
C12 N8 C15 107.78(18) . . ?
C12 N8 C24 126.4(2) . . ?
C15 N8 C24 125.9(2) . . ?
C10 C9 H9 119.5 . . ?
C20 C9 H9 119.5 . . ?
C20 C9 C10 121.0(2) . . ?
C9 C10 C7 120.0(2) . . ?
C13 C10 C7 121.3(2) . . ?
C13 C10 C9 118.1(2) . . ?
C6 C11 H11 119.8 . . ?
C6 C11 C16 120.4(2) . . ?
C16 C11 H11 119.8 . . ?
C6 C12 C5 123.9(2) . . ?
N8 C12 C5 109.08(18) . . ?
N8 C12 C6 127.0(2) . . ?
C10 C13 H13 119.4 . . ?
C10 C13 C17 121.2(2) . . ?
C17 C13 H13 119.4 . . ?
C19 C14 P1 118.7(2) . . ?
C19 C14 C21 107.3(2) . . ?
C21 C14 P1 107.56(19) . . ?
C23 C14 P1 105.39(18) . . ?
C23 C14 C19 109.3(3) . . ?
C23 C14 C21 108.1(2) . . ?
C7 C15 N8 112.1(2) . . ?
C7 C15 H15 124.0 . . ?
N8 C15 H15 124.0 . . ?
C4 C16 C11 123.3(2) . . ?
C4 C16 H16 118.3 . . ?
C11 C16 H16 118.3 . . ?
C13 C17 H17 120.5 . . ?
C22 C17 C13 119.1(2) . . ?
C22 C17 H17 120.5 . . ?
C25 C18 P1 104.7(2) . . ?
C1 C18 P1 108.2(2) . . ?
C1 C18 C25 107.2(3) . . ?
C2 C18 P1 116.4(2) . . ?
C2 C18 C25 109.3(3) . . ?
C2 C18 C1 110.5(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20 120.3 . . ?
C22 C20 C9 119.5(3) . . ?
C22 C20 H20 120.3 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 Cl2 119.6(2) . . ?
C20 C22 Cl2 119.2(2) . . ?
C20 C22 C17 121.3(2) . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N8 C24 H24A 109.5 . . ?
N8 C24 H24B 109.5 . . ?
N8 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C1 H1A 109.5 . . ?
C18 C1 H1B 109.5 . . ?
C18 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C18 C2 H2A 109.5 . . ?
C18 C2 H2B 109.5 . . ?
C18 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C4 C5 C7 0.4(4) . . . . ?
P1 C4 C5 C12 -177.61(15) . . . . ?
P1 C4 C16 C11 177.3(2) . . . . ?
O3 P1 C4 C5 -15.4(2) . . . . ?
O3 P1 C4 C16 167.25(19) . . . . ?
O3 P1 C14 C19 165.2(2) . . . . ?
O3 P1 C14 C21 43.2(2) . . . . ?
O3 P1 C14 C23 -72.0(2) . . . . ?
O3 P1 C18 C25 58.1(2) . . . . ?
O3 P1 C18 C1 -56.0(3) . . . . ?
O3 P1 C18 C2 178.8(3) . . . . ?
C4 P1 C14 C19 -73.5(2) . . . . ?
C4 P1 C14 C21 164.55(19) . . . . ?
C4 P1 C14 C23 49.3(2) . . . . ?
C4 P1 C18 C25 -63.3(2) . . . . ?
C4 P1 C18 C1 -177.4(2) . . . . ?
C4 P1 C18 C2 57.5(3) . . . . ?
C4 C5 C7 C10 1.1(4) . . . . ?
C4 C5 C7 C15 -178.2(2) . . . . ?
C4 C5 C12 C6 0.8(3) . . . . ?
C4 C5 C12 N8 178.84(18) . . . . ?
C5 C4 C16 C11 -0.2(4) . . . . ?
C5 C7 C10 C9 -96.9(3) . . . . ?
C5 C7 C10 C13 91.9(3) . . . . ?
C5 C7 C15 N8 -0.1(3) . . . . ?
C6 C11 C16 C4 0.2(4) . . . . ?
C7 C5 C12 C6 -177.8(2) . . . . ?
C7 C5 C12 N8 0.2(2) . . . . ?
C7 C10 C13 C17 170.9(2) . . . . ?
C9 C10 C13 C17 -0.5(4) . . . . ?
C9 C20 C22 Cl2 179.1(2) . . . . ?
C9 C20 C22 C17 -0.8(5) . . . . ?
C10 C7 C15 N8 -179.58(19) . . . . ?
C10 C9 C20 C22 0.7(5) . . . . ?
C10 C13 C17 C22 0.4(4) . . . . ?
C11 C6 C12 C5 -0.9(3) . . . . ?
C11 C6 C12 N8 -178.5(2) . . . . ?
C12 C5 C7 C10 179.2(2) . . . . ?
C12 C5 C7 C15 -0.1(2) . . . . ?
C12 C6 C11 C16 0.3(4) . . . . ?
C12 N8 C15 C7 0.3(3) . . . . ?
C13 C17 C22 Cl2 -179.6(2) . . . . ?
C13 C17 C22 C20 0.2(4) . . . . ?
C14 P1 C4 C5 -133.61(19) . . . . ?
C14 P1 C4 C16 49.1(2) . . . . ?
C14 P1 C18 C25 178.4(2) . . . . ?
C14 P1 C18 C1 64.3(2) . . . . ?
C14 P1 C18 C2 -60.9(3) . . . . ?
C15 C7 C10 C9 82.4(3) . . . . ?
C15 C7 C10 C13 -88.9(3) . . . . ?
C15 N8 C12 C5 -0.3(2) . . . . ?
C15 N8 C12 C6 177.6(2) . . . . ?
C16 C4 C5 C7 177.7(2) . . . . ?
C16 C4 C5 C12 -0.3(3) . . . . ?
C18 P1 C4 C5 104.2(2) . . . . ?
C18 P1 C4 C16 -73.1(2) . . . . ?
C18 P1 C14 C19 43.6(3) . . . . ?
C18 P1 C14 C21 -78.4(2) . . . . ?
C18 P1 C14 C23 166.38(18) . . . . ?
C20 C9 C10 C7 -171.6(2) . . . . ?
C20 C9 C10 C13 -0.1(4) . . . . ?
C24 N8 C12 C5 178.4(2) . . . . ?
C24 N8 C12 C6 -3.6(4) . . . . ?
C24 N8 C15 C7 -178.5(2) . . . . ?

_olex2_date_sample_data_collection 2020-07-06
_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 2.412
_oxdiff_exptl_absorpt_empirical_full_min 0.678
####################################################################### 
# 
# 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_niuy_0610
_audit_block_doi                 10.5517/ccdc.csd.cc26kx4v
_database_code_depnum_ccdc_archive 'CCDC 2042997'
loop_
_audit_author_name
_audit_author_address
niuy-niu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-06-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H32 N O P'
_chemical_formula_sum            'C24 H32 N O P'
_chemical_formula_weight         381.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.5242(3)
_cell_length_b                   15.7499(3)
_cell_length_c                   19.4992(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4460.55(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3699
_cell_measurement_temperature    293.37(10)
_cell_measurement_theta_max      69.6720
_cell_measurement_theta_min      3.8250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10855
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.535
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.37(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  62.00   1.00    1.00    --    0.00  57.00   0.00   27
  2  ω     43.00 122.00   1.00    1.00    --   54.00   0.00-150.00   79
  3  ω     92.00 134.00   1.00    1.10    --  108.00  63.00-180.00   42
  4  ω    138.00 174.00   1.00    1.10    --  108.00  63.00-180.00   36
  5  ω    102.00 160.00   1.00    1.10    --  108.00  50.00-150.00   58
  6  ω     90.00 117.00   1.00    1.10    --  108.00  50.00-180.00   27
  7  ω     38.00 128.00   1.00    1.10    --  108.00 -50.00  30.00   90
  8  ω     36.00 112.00   1.00    1.10    --  108.00-111.00-120.00   76
  9  ω     26.00  83.00   1.00    1.00    --   54.00-125.00 -90.00   57
 10  ω     26.00  79.00   1.00    1.00    --   54.00-125.00  60.00   53
 11  ω    -69.00  10.00   1.00    1.00    --    0.00 -57.00 -30.00   79
 12  ω    136.00 163.00   1.00    1.10    --  108.00 108.00  23.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0166276000
_diffrn_orient_matrix_UB_12      0.0861316000
_diffrn_orient_matrix_UB_13      -0.0353825000
_diffrn_orient_matrix_UB_21      0.0747960000
_diffrn_orient_matrix_UB_22      -0.0407973000
_diffrn_orient_matrix_UB_23      -0.0452741000
_diffrn_orient_matrix_UB_31      -0.0733300000
_diffrn_orient_matrix_UB_32      -0.0221505000
_diffrn_orient_matrix_UB_33      -0.0542000000
_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                3198
_reflns_number_total             3922
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.042
_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)+(0.0668P)²+1.0889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58277(3) 0.24328(3) 0.31522(2) 0.03767(16) Uani 1 1 d . . . . .
O1 O 0.61896(9) 0.16994(8) 0.35454(7) 0.0467(3) Uani 1 1 d . . . . .
C2 C 0.78215(12) 0.29234(11) 0.41344(9) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.73812(12) 0.34129(10) 0.36007(9) 0.0344(4) Uani 1 1 d . . . . .
N4 N 0.86179(11) 0.41444(9) 0.40019(9) 0.0479(4) Uani 1 1 d . . . . .
C5 C 0.66022(13) 0.33367(11) 0.31625(9) 0.0395(4) Uani 1 1 d . . . . .
C6 C 0.76602(13) 0.20834(11) 0.44700(9) 0.0394(4) Uani 1 1 d . . . . .
C7 C 0.77048(15) 0.48388(11) 0.31002(11) 0.0477(5) Uani 1 1 d . . . . .
H7 H 0.806497 0.532667 0.308465 0.057 Uiso 1 1 calc R U . . .
C8 C 0.79111(12) 0.41747(10) 0.35421(10) 0.0394(4) Uani 1 1 d . . . . .
C9 C 0.64110(15) 0.40131(12) 0.27240(12) 0.0545(5) Uani 1 1 d . . . . .
H9 H 0.589787 0.397370 0.244053 0.065 Uiso 1 1 calc R U . . .
C10 C 0.81239(16) 0.13700(12) 0.42570(11) 0.0510(5) Uani 1 1 d . . . . .
H10 H 0.847121 0.138987 0.385663 0.061 Uiso 1 1 calc R U . . .
C11 C 0.69474(16) 0.47448(12) 0.26879(12) 0.0557(5) Uani 1 1 d . . . . .
H11 H 0.679026 0.517331 0.238125 0.067 Uiso 1 1 calc R U . . .
C12 C 0.71453(17) 0.20226(13) 0.50642(11) 0.0567(5) Uani 1 1 d . . . . .
H12 H 0.681849 0.249226 0.522003 0.068 Uiso 1 1 calc R U . . .
C13 C 0.85539(14) 0.33940(12) 0.43499(10) 0.0479(5) Uani 1 1 d . . . . .
H13 H 0.896053 0.322483 0.469204 0.057 Uiso 1 1 calc R U . . .
C14 C 0.57031(15) 0.20825(13) 0.22389(11) 0.0503(5) Uani 1 1 d . . . . .
C15 C 0.52599(19) 0.11973(15) 0.22444(14) 0.0741(7) Uani 1 1 d . . . . .
H15A H 0.559046 0.083568 0.255501 0.111 Uiso 1 1 calc R U . . .
H15B H 0.528151 0.095992 0.179125 0.111 Uiso 1 1 calc R U . . .
H15C H 0.463060 0.124279 0.239050 0.111 Uiso 1 1 calc R U . . .
C16 C 0.7579(2) 0.05614(14) 0.52221(12) 0.0675(7) Uani 1 1 d . . . . .
C17 C 0.93185(17) 0.47895(14) 0.41014(15) 0.0675(7) Uani 1 1 d . . . . .
H17A H 0.973951 0.478051 0.372194 0.101 Uiso 1 1 calc R U . . .
H17B H 0.964751 0.467718 0.451862 0.101 Uiso 1 1 calc R U . . .
H17C H 0.903192 0.533769 0.412940 0.101 Uiso 1 1 calc R U . . .
C18 C 0.80820(19) 0.06204(13) 0.46299(13) 0.0637(6) Uani 1 1 d . . . . .
H18 H 0.840269 0.014716 0.447398 0.076 Uiso 1 1 calc R U . . .
C19 C 0.7111(2) 0.12674(16) 0.54307(13) 0.0742(8) Uani 1 1 d . . . . .
H19 H 0.675987 0.124183 0.582895 0.089 Uiso 1 1 calc R U . . .
C20 C 0.66894(18) 0.19951(18) 0.19742(14) 0.0735(7) Uani 1 1 d . . . . .
H20A H 0.696219 0.254797 0.193288 0.110 Uiso 1 1 calc R U . . .
H20B H 0.668301 0.172338 0.153349 0.110 Uiso 1 1 calc R U . . .
H20C H 0.704227 0.165917 0.228984 0.110 Uiso 1 1 calc R U . . .
C21 C 0.47402(15) 0.28061(15) 0.35509(13) 0.0596(6) Uani 1 1 d . . . . .
C22 C 0.40872(16) 0.2054(2) 0.36162(18) 0.0910(10) Uani 1 1 d . . . . .
H22A H 0.386437 0.189757 0.317021 0.136 Uiso 1 1 calc R U . . .
H22B H 0.357716 0.220712 0.390375 0.136 Uiso 1 1 calc R U . . .
H22C H 0.440866 0.158187 0.381594 0.136 Uiso 1 1 calc R U . . .
C23 C 0.7569(3) -0.02533(17) 0.56352(16) 0.1193(15) Uani 1 1 d . . . . .
H23A H 0.752472 -0.072986 0.533011 0.179 Uiso 1 1 calc R U . . .
H23B H 0.704976 -0.025101 0.593970 0.179 Uiso 1 1 calc R U . . .
H23C H 0.812657 -0.029511 0.589763 0.179 Uiso 1 1 calc R U . . .
C24 C 0.5018(2) 0.3063(2) 0.42834(16) 0.0983(11) Uani 1 1 d . . . . .
H24A H 0.531187 0.259207 0.450613 0.147 Uiso 1 1 calc R U . . .
H24B H 0.447834 0.322329 0.453685 0.147 Uiso 1 1 calc R U . . .
H24C H 0.543611 0.353440 0.426433 0.147 Uiso 1 1 calc R U . . .
C25 C 0.4252(2) 0.3547(2) 0.3201(2) 0.1228(15) Uani 1 1 d . . . . .
H25A H 0.465785 0.402758 0.318432 0.184 Uiso 1 1 calc R U . . .
H25B H 0.370926 0.369274 0.345630 0.184 Uiso 1 1 calc R U . . .
H25C H 0.408223 0.338629 0.274362 0.184 Uiso 1 1 calc R U . . .
C26 C 0.5147(2) 0.26384(18) 0.17434(14) 0.0835(9) Uani 1 1 d . . . . .
H26A H 0.454190 0.272985 0.192662 0.125 Uiso 1 1 calc R U . . .
H26B H 0.510034 0.235861 0.130741 0.125 Uiso 1 1 calc R U . . .
H26C H 0.545179 0.317471 0.168597 0.125 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4827(13) . ?
P1 C5 1.8144(18) . ?
P1 C14 1.873(2) . ?
P1 C21 1.856(2) . ?
C2 C3 1.444(2) . ?
C2 C6 1.494(2) . ?
C2 C13 1.363(3) . ?
C3 C5 1.423(2) . ?
C3 C8 1.430(2) . ?
N4 C8 1.364(2) . ?
N4 C13 1.366(2) . ?
N4 C17 1.451(2) . ?
C5 C9 1.394(3) . ?
C6 C10 1.374(3) . ?
C6 C12 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C7 C11 1.371(3) . ?
C9 H9 0.9300 . ?
C9 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C18 1.388(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C19 1.388(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.536(3) . ?
C14 C20 1.529(3) . ?
C14 C26 1.534(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.369(4) . ?
C16 C19 1.365(4) . ?
C16 C23 1.515(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.523(3) . ?
C21 C24 1.538(4) . ?
C21 C25 1.526(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C5 112.69(8) . . ?
O1 P1 C14 107.24(9) . . ?
O1 P1 C21 109.39(9) . . ?
C5 P1 C14 107.54(9) . . ?
C5 P1 C21 105.93(10) . . ?
C21 P1 C14 114.16(11) . . ?
C3 C2 C6 135.94(16) . . ?
C13 C2 C3 106.10(15) . . ?
C13 C2 C6 117.96(17) . . ?
C5 C3 C2 137.70(16) . . ?
C5 C3 C8 116.79(15) . . ?
C8 C3 C2 105.50(15) . . ?
C8 N4 C13 107.79(15) . . ?
C8 N4 C17 126.25(17) . . ?
C13 N4 C17 125.96(18) . . ?
C3 C5 P1 124.46(13) . . ?
C9 C5 P1 117.99(14) . . ?
C9 C5 C3 117.53(16) . . ?
C10 C6 C2 120.97(17) . . ?
C10 C6 C12 117.50(18) . . ?
C12 C6 C2 120.87(17) . . ?
C8 C7 H7 121.4 . . ?
C11 C7 H7 121.4 . . ?
C11 C7 C8 117.13(17) . . ?
N4 C8 C3 108.86(16) . . ?
N4 C8 C7 126.65(17) . . ?
C7 C8 C3 124.46(17) . . ?
C5 C9 H9 118.2 . . ?
C11 C9 C5 123.51(19) . . ?
C11 C9 H9 118.2 . . ?
C6 C10 H10 119.5 . . ?
C6 C10 C18 121.0(2) . . ?
C18 C10 H10 119.5 . . ?
C7 C11 C9 120.57(18) . . ?
C7 C11 H11 119.7 . . ?
C9 C11 H11 119.7 . . ?
C6 C12 H12 119.7 . . ?
C6 C12 C19 120.7(2) . . ?
C19 C12 H12 119.7 . . ?
C2 C13 N4 111.75(18) . . ?
C2 C13 H13 124.1 . . ?
N4 C13 H13 124.1 . . ?
C15 C14 P1 107.53(16) . . ?
C20 C14 P1 104.89(15) . . ?
C20 C14 C15 108.3(2) . . ?
C20 C14 C26 109.4(2) . . ?
C26 C14 P1 118.80(17) . . ?
C26 C14 C15 107.58(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C23 120.7(3) . . ?
C19 C16 C18 117.5(2) . . ?
C19 C16 C23 121.8(3) . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18 119.2 . . ?
C16 C18 C10 121.5(2) . . ?
C16 C18 H18 119.2 . . ?
C12 C19 H19 119.1 . . ?
C16 C19 C12 121.8(2) . . ?
C16 C19 H19 119.1 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 P1 108.56(17) . . ?
C22 C21 C24 106.9(2) . . ?
C22 C21 C25 110.1(2) . . ?
C24 C21 P1 104.43(17) . . ?
C25 C21 P1 116.78(18) . . ?
C25 C21 C24 109.6(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C26 H26A 109.5 . . ?
C14 C26 H26B 109.5 . . ?
C14 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C9 C11 179.46(18) . . . . ?
O1 P1 C5 C3 -11.71(18) . . . . ?
O1 P1 C5 C9 169.94(15) . . . . ?
O1 P1 C14 C15 44.31(17) . . . . ?
O1 P1 C14 C20 -70.78(17) . . . . ?
O1 P1 C14 C26 166.67(18) . . . . ?
O1 P1 C21 C22 -53.3(2) . . . . ?
O1 P1 C21 C24 60.4(2) . . . . ?
O1 P1 C21 C25 -178.4(2) . . . . ?
C2 C3 C5 P1 -1.0(3) . . . . ?
C2 C3 C5 C9 177.4(2) . . . . ?
C2 C3 C8 N4 0.29(19) . . . . ?
C2 C3 C8 C7 -177.74(18) . . . . ?
C2 C6 C10 C18 170.2(2) . . . . ?
C2 C6 C12 C19 -170.2(2) . . . . ?
C3 C2 C6 C10 96.3(3) . . . . ?
C3 C2 C6 C12 -93.1(3) . . . . ?
C3 C2 C13 N4 0.3(2) . . . . ?
C3 C5 C9 C11 1.0(3) . . . . ?
C5 P1 C14 C15 165.77(15) . . . . ?
C5 P1 C14 C20 50.67(17) . . . . ?
C5 P1 C14 C26 -71.9(2) . . . . ?
C5 P1 C21 C22 -175.02(19) . . . . ?
C5 P1 C21 C24 -61.28(19) . . . . ?
C5 P1 C21 C25 59.9(3) . . . . ?
C5 C3 C8 N4 179.26(16) . . . . ?
C5 C3 C8 C7 1.2(3) . . . . ?
C5 C9 C11 C7 -0.8(4) . . . . ?
C6 C2 C3 C5 1.2(4) . . . . ?
C6 C2 C3 C8 179.8(2) . . . . ?
C6 C2 C13 N4 -179.87(16) . . . . ?
C6 C10 C18 C16 0.0(4) . . . . ?
C6 C12 C19 C16 0.0(4) . . . . ?
C8 C3 C5 P1 -179.52(13) . . . . ?
C8 C3 C5 C9 -1.2(2) . . . . ?
C8 N4 C13 C2 -0.1(2) . . . . ?
C8 C7 C11 C9 0.7(3) . . . . ?
C10 C6 C12 C19 0.6(3) . . . . ?
C11 C7 C8 C3 -1.0(3) . . . . ?
C11 C7 C8 N4 -178.7(2) . . . . ?
C12 C6 C10 C18 -0.6(3) . . . . ?
C13 C2 C3 C5 -179.0(2) . . . . ?
C13 C2 C3 C8 -0.33(19) . . . . ?
C13 C2 C6 C10 -83.5(2) . . . . ?
C13 C2 C6 C12 87.1(2) . . . . ?
C13 N4 C8 C3 -0.1(2) . . . . ?
C13 N4 C8 C7 177.84(19) . . . . ?
C14 P1 C5 C3 -129.68(16) . . . . ?
C14 P1 C5 C9 51.96(18) . . . . ?
C14 P1 C21 C22 66.8(2) . . . . ?
C14 P1 C21 C24 -179.42(18) . . . . ?
C14 P1 C21 C25 -58.2(3) . . . . ?
C17 N4 C8 C3 179.4(2) . . . . ?
C17 N4 C8 C7 -2.6(3) . . . . ?
C17 N4 C13 C2 -179.6(2) . . . . ?
C18 C16 C19 C12 -0.6(4) . . . . ?
C19 C16 C18 C10 0.6(4) . . . . ?
C21 P1 C5 C3 107.87(17) . . . . ?
C21 P1 C5 C9 -70.49(18) . . . . ?
C21 P1 C14 C15 -77.03(18) . . . . ?
C21 P1 C14 C20 167.88(16) . . . . ?
C21 P1 C14 C26 45.3(2) . . . . ?
C23 C16 C18 C10 -177.8(3) . . . . ?
C23 C16 C19 C12 177.8(3) . . . . ?

_olex2_date_sample_data_collection 2020-06-10
_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 2.273
_oxdiff_exptl_absorpt_empirical_full_min 0.492
####################################################################### 
# 
# 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_niuy_1029
_database_code_depnum_ccdc_archive 'CCDC 2043003'
loop_
_audit_author_name
_audit_author_address
niuuuuuuu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_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         'C24 H32 N O P'
_chemical_formula_sum            'C24 H32 N O P'
_chemical_formula_weight         381.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.4047(7)
_cell_length_b                   7.95437(17)
_cell_length_c                   17.7118(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.0211(19)
_cell_angle_gamma                90
_cell_volume                     4562.54(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    293.14(10)
_cell_measurement_theta_max      69.6400
_cell_measurement_theta_min      4.9850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8667
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.564
_diffrn_reflns_theta_max         66.564
_diffrn_reflns_theta_min         4.997
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.14(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  71.00   1.00    2.00    --   54.00 -57.00   0.00   80
  2  ω     60.00 116.00   1.00    2.00    --  108.00-111.00  30.00   56
  3  ω     44.00  71.00   1.00    2.00    --  108.00-111.00 -30.00   27
  4  ω     48.00 109.00   1.00    2.00    --  108.00-111.00-120.00   61
  5  ω     13.00  95.00   1.00    2.00    --   54.00 -99.00 -60.00   82
  6  ω     10.00 120.00   1.00    2.00    --   54.00  19.00 -90.00  110
  7  ω     87.00 152.00   1.00    2.00    --  108.00  38.00-120.00   65
  8  ω    104.00 169.00   1.00    2.00    --  108.00 111.00 -90.00   65
  9  ω    111.00 176.00   1.00    2.00    --  108.00 111.00  30.00   65
 10  ω    121.00 175.00   1.00    2.00    --  108.00  38.00 150.00   54
 11  ω     88.00 114.00   1.00    2.00    --  108.00  38.00 150.00   26
 12  ω     37.00  84.00   1.00    2.00    --  108.00 -38.00 120.00   47
 13  ω     31.00  56.00   1.00    2.00    --   54.00  38.00 150.00   25
 14  ω     15.00  69.00   1.00    1.00    --    0.00  57.00  30.00   54
 15  ω    -19.00  18.00   1.00    1.00    --    0.00  57.00 -30.00   37
 16  ω    -48.00  -8.00   1.00    1.00    --    0.00 132.00-144.00   40
 17  ω     60.00 138.00   1.00    2.00    --  108.00 178.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0006873000
_diffrn_orient_matrix_UB_12      0.1936080000
_diffrn_orient_matrix_UB_13      0.0017736000
_diffrn_orient_matrix_UB_21      0.0464178000
_diffrn_orient_matrix_UB_22      0.0017481000
_diffrn_orient_matrix_UB_23      0.0219940000
_diffrn_orient_matrix_UB_31      0.0103926000
_diffrn_orient_matrix_UB_32      0.0045702000
_diffrn_orient_matrix_UB_33      -0.0841922000
_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                3420
_reflns_number_total             4041
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.073
_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)+(0.0677P)²+1.5418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C15(H15), C17(H17), C18(H18), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C1(H1A,H1B,
 H1C), C2AA(H2AA,H2AB,H2AC), C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC),
 C3AA(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.34753(2) 0.01804(6) 0.60223(2) 0.04613(16) Uani 1 1 d . . . . .
O2 O 0.36447(4) 0.18515(16) 0.62423(8) 0.0602(4) Uani 1 1 d . . . . .
N3 N 0.49625(4) -0.15542(19) 0.63889(8) 0.0508(4) Uani 1 1 d . . . . .
C4 C 0.42821(5) -0.1021(2) 0.61975(8) 0.0411(4) Uani 1 1 d . . . . .
C5 C 0.45085(5) 0.0505(2) 0.61255(8) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.439674 0.155814 0.601719 0.049 Uiso 1 1 calc R U . . .
C6 C 0.49186(5) 0.0148(2) 0.62435(9) 0.0436(4) Uani 1 1 d . . . . .
C7 C 0.56766(6) 0.3508(2) 0.57476(11) 0.0568(5) Uani 1 1 d . . . . .
H7 H 0.572706 0.421414 0.534275 0.068 Uiso 1 1 calc R U . . .
C8 C 0.38578(5) -0.1458(2) 0.61508(9) 0.0463(4) Uani 1 1 d . . . . .
C9 C 0.33335(6) 0.0167(3) 0.50013(10) 0.0580(5) Uani 1 1 d . . . . .
C10 C 0.52701(5) 0.1310(2) 0.62818(8) 0.0449(4) Uani 1 1 d . . . . .
C11 C 0.37286(6) 0.0704(3) 0.46111(11) 0.0709(6) Uani 1 1 d . . . . .
H11A H 0.381824 0.177661 0.480404 0.106 Uiso 1 1 calc R U . . .
H11B H 0.367327 0.078795 0.407635 0.106 Uiso 1 1 calc R U . . .
H11C H 0.394112 -0.011586 0.470911 0.106 Uiso 1 1 calc R U . . .
C12 C 0.45788(6) -0.2290(2) 0.63479(9) 0.0484(4) Uani 1 1 d . . . . .
C13 C 0.53517(5) 0.2393(2) 0.56923(9) 0.0488(4) Uani 1 1 d . . . . .
H13 H 0.518495 0.236733 0.525421 0.059 Uiso 1 1 calc R U . . .
C14 C 0.59306(6) 0.3600(2) 0.63942(11) 0.0565(5) Uani 1 1 d . . . . .
C15 C 0.44744(7) -0.3982(2) 0.64167(11) 0.0629(5) Uani 1 1 d . . . . .
H15 H 0.467489 -0.479899 0.651214 0.075 Uiso 1 1 calc R U . . .
C16 C 0.32193(8) -0.0771(4) 0.74204(12) 0.0941(9) Uani 1 1 d . . . . .
H16A H 0.334789 -0.185497 0.738777 0.141 Uiso 1 1 calc R U . . .
H16B H 0.300434 -0.081587 0.777920 0.141 Uiso 1 1 calc R U . . .
H16C H 0.342171 0.004720 0.758073 0.141 Uiso 1 1 calc R U . . .
C17 C 0.55294(6) 0.1388(3) 0.69266(10) 0.0585(5) Uani 1 1 d . . . . .
H17 H 0.548415 0.066476 0.732790 0.070 Uiso 1 1 calc R U . . .
C18 C 0.58506(6) 0.2516(3) 0.69792(11) 0.0622(5) Uani 1 1 d . . . . .
H18 H 0.601717 0.254801 0.741738 0.075 Uiso 1 1 calc R U . . .
C19 C 0.53494(7) -0.2488(3) 0.64522(13) 0.0745(6) Uani 1 1 d . . . . .
H19A H 0.538338 -0.313692 0.600157 0.112 Uiso 1 1 calc R U . . .
H19B H 0.534406 -0.322736 0.688027 0.112 Uiso 1 1 calc R U . . .
H19C H 0.557550 -0.171562 0.651653 0.112 Uiso 1 1 calc R U . . .
C20 C 0.37642(7) -0.3165(2) 0.62138(11) 0.0611(5) Uani 1 1 d . . . . .
H20 H 0.348899 -0.349472 0.617101 0.073 Uiso 1 1 calc R U . . .
C21 C 0.30332(6) -0.0275(3) 0.66399(11) 0.0682(6) Uani 1 1 d . . . . .
C22 C 0.40641(8) -0.4394(2) 0.63378(12) 0.0688(6) Uani 1 1 d . . . . .
H22 H 0.398513 -0.551517 0.636768 0.083 Uiso 1 1 calc R U . . .
C1 C 0.29999(8) 0.1476(4) 0.48260(14) 0.0991(10) Uani 1 1 d . . . . .
H1A H 0.274094 0.108674 0.500662 0.149 Uiso 1 1 calc R U . . .
H1B H 0.297537 0.165086 0.428998 0.149 Uiso 1 1 calc R U . . .
H1C H 0.307341 0.251599 0.507110 0.149 Uiso 1 1 calc R U . . .
C2AA C 0.32085(8) -0.1555(4) 0.46887(12) 0.0870(8) Uani 1 1 d . . . . .
H2AA H 0.342113 -0.235768 0.481478 0.131 Uiso 1 1 calc R U . . .
H2AB H 0.317093 -0.148742 0.414950 0.131 Uiso 1 1 calc R U . . .
H2AC H 0.295480 -0.190217 0.490531 0.131 Uiso 1 1 calc R U . . .
C0AA C 0.28015(9) 0.1399(4) 0.67307(17) 0.1064(10) Uani 1 1 d . . . . .
H0AA H 0.299132 0.224747 0.691059 0.160 Uiso 1 1 calc R U . . .
H0AB H 0.258760 0.125764 0.708676 0.160 Uiso 1 1 calc R U . . .
H0AC H 0.268104 0.173555 0.625128 0.160 Uiso 1 1 calc R U . . .
C1AA C 0.27266(8) -0.1622(5) 0.63667(16) 0.1085(11) Uani 1 1 d . . . . .
H1AA H 0.259272 -0.126459 0.590180 0.163 Uiso 1 1 calc R U . . .
H1AB H 0.252335 -0.178984 0.674093 0.163 Uiso 1 1 calc R U . . .
H1AC H 0.287097 -0.265619 0.628581 0.163 Uiso 1 1 calc R U . . .
C3AA C 0.62814(8) 0.4842(3) 0.64627(17) 0.0853(7) Uani 1 1 d . . . . .
H3AA H 0.634921 0.522926 0.596901 0.128 Uiso 1 1 calc R U . . .
H3AB H 0.651815 0.430664 0.669845 0.128 Uiso 1 1 calc R U . . .
H3AC H 0.620011 0.577992 0.676432 0.128 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4851(13) . ?
P1 C8 1.8075(18) . ?
P1 C9 1.8501(18) . ?
P1 C21 1.868(2) . ?
N3 C6 1.385(2) . ?
N3 C12 1.374(2) . ?
N3 C19 1.458(2) . ?
C4 C5 1.426(2) . ?
C4 C8 1.418(2) . ?
C4 C12 1.413(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(2) . ?
C6 C10 1.466(2) . ?
C7 H7 0.9300 . ?
C7 C13 1.377(3) . ?
C7 C14 1.389(3) . ?
C8 C20 1.397(2) . ?
C9 C11 1.537(3) . ?
C9 C1 1.525(3) . ?
C9 C2AA 1.527(3) . ?
C10 C13 1.386(2) . ?
C10 C17 1.395(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C18 1.380(3) . ?
C14 C3AA 1.507(3) . ?
C15 H15 0.9300 . ?
C15 C22 1.372(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C21 1.540(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C22 1.390(3) . ?
C21 C0AA 1.540(4) . ?
C21 C1AA 1.528(3) . ?
C22 H22 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2AA H2AA 0.9600 . ?
C2AA H2AB 0.9600 . ?
C2AA H2AC 0.9600 . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C1AA H1AA 0.9600 . ?
C1AA H1AB 0.9600 . ?
C1AA H1AC 0.9600 . ?
C3AA H3AA 0.9600 . ?
C3AA H3AB 0.9600 . ?
C3AA H3AC 0.9600 . ?

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
O2 P1 C8 111.51(7) . . ?
O2 P1 C9 109.78(9) . . ?
O2 P1 C21 107.68(9) . . ?
C8 P1 C9 105.34(8) . . ?
C8 P1 C21 108.85(10) . . ?
C9 P1 C21 113.72(9) . . ?
C6 N3 C19 126.51(17) . . ?
C12 N3 C6 108.65(14) . . ?
C12 N3 C19 124.14(17) . . ?
C8 C4 C5 134.79(15) . . ?
C12 C4 C5 106.02(14) . . ?
C12 C4 C8 119.19(15) . . ?
C4 C5 H5 126.0 . . ?
C6 C5 C4 108.07(15) . . ?
C6 C5 H5 126.0 . . ?
N3 C6 C10 122.21(15) . . ?
C5 C6 N3 108.90(15) . . ?
C5 C6 C10 128.72(16) . . ?
C13 C7 H7 119.3 . . ?
C13 C7 C14 121.48(18) . . ?
C14 C7 H7 119.3 . . ?
C4 C8 P1 119.32(12) . . ?
C20 C8 P1 124.13(15) . . ?
C20 C8 C4 116.54(17) . . ?
C11 C9 P1 104.83(13) . . ?
C1 C9 P1 110.17(14) . . ?
C1 C9 C11 108.32(19) . . ?
C1 C9 C2AA 111.2(2) . . ?
C2AA C9 P1 114.40(15) . . ?
C2AA C9 C11 107.52(19) . . ?
C13 C10 C6 121.69(14) . . ?
C13 C10 C17 117.61(17) . . ?
C17 C10 C6 120.69(16) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C4 108.33(15) . . ?
N3 C12 C15 128.93(18) . . ?
C15 C12 C4 122.73(18) . . ?
C7 C13 C10 120.81(15) . . ?
C7 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C7 C14 C3AA 121.6(2) . . ?
C18 C14 C7 117.69(18) . . ?
C18 C14 C3AA 120.69(19) . . ?
C12 C15 H15 121.3 . . ?
C22 C15 C12 117.31(19) . . ?
C22 C15 H15 121.3 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 C16 H16A 109.5 . . ?
C21 C16 H16B 109.5 . . ?
C21 C16 H16C 109.5 . . ?
C10 C17 H17 119.4 . . ?
C18 C17 C10 121.14(18) . . ?
C18 C17 H17 119.4 . . ?
C14 C18 H18 119.4 . . ?
C17 C18 C14 121.27(17) . . ?
C17 C18 H18 119.4 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 H20 118.5 . . ?
C22 C20 C8 122.91(19) . . ?
C22 C20 H20 118.5 . . ?
C16 C21 P1 106.93(15) . . ?
C0AA C21 P1 106.29(17) . . ?
C0AA C21 C16 107.8(2) . . ?
C1AA C21 P1 116.99(15) . . ?
C1AA C21 C16 109.5(2) . . ?
C1AA C21 C0AA 109.0(2) . . ?
C15 C22 C20 121.21(18) . . ?
C15 C22 H22 119.4 . . ?
C20 C22 H22 119.4 . . ?
C9 C1 H1A 109.5 . . ?
C9 C1 H1B 109.5 . . ?
C9 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C2AA H2AA 109.5 . . ?
C9 C2AA H2AB 109.5 . . ?
C9 C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
C21 C0AA H0AA 109.5 . . ?
C21 C0AA H0AB 109.5 . . ?
C21 C0AA H0AC 109.5 . . ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C21 C1AA H1AA 109.5 . . ?
C21 C1AA H1AB 109.5 . . ?
C21 C1AA H1AC 109.5 . . ?
H1AA C1AA H1AB 109.5 . . ?
H1AA C1AA H1AC 109.5 . . ?
H1AB C1AA H1AC 109.5 . . ?
C14 C3AA H3AA 109.5 . . ?
C14 C3AA H3AB 109.5 . . ?
C14 C3AA H3AC 109.5 . . ?
H3AA C3AA H3AB 109.5 . . ?
H3AA C3AA H3AC 109.5 . . ?
H3AB C3AA H3AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C20 C22 -177.78(15) . . . . ?
O2 P1 C8 C4 -19.75(15) . . . . ?
O2 P1 C8 C20 159.83(15) . . . . ?
O2 P1 C9 C11 54.85(16) . . . . ?
O2 P1 C9 C1 -61.49(18) . . . . ?
O2 P1 C9 C2AA 172.37(15) . . . . ?
O2 P1 C21 C16 -75.78(19) . . . . ?
O2 P1 C21 C0AA 39.13(18) . . . . ?
O2 P1 C21 C1AA 161.1(2) . . . . ?
N3 C6 C10 C13 128.36(18) . . . . ?
N3 C6 C10 C17 -53.2(2) . . . . ?
N3 C12 C15 C22 -178.76(17) . . . . ?
C4 C5 C6 N3 -0.02(17) . . . . ?
C4 C5 C6 C10 -175.30(14) . . . . ?
C4 C8 C20 C22 1.8(3) . . . . ?
C4 C12 C15 C22 -0.5(3) . . . . ?
C5 C4 C8 P1 -4.2(2) . . . . ?
C5 C4 C8 C20 176.20(17) . . . . ?
C5 C4 C12 N3 1.87(17) . . . . ?
C5 C4 C12 C15 -176.71(16) . . . . ?
C5 C6 C10 C13 -56.9(2) . . . . ?
C5 C6 C10 C17 121.49(19) . . . . ?
C6 N3 C12 C4 -1.92(18) . . . . ?
C6 N3 C12 C15 176.55(18) . . . . ?
C6 C10 C13 C7 178.18(16) . . . . ?
C6 C10 C17 C18 -177.58(17) . . . . ?
C7 C14 C18 C17 -0.3(3) . . . . ?
C8 P1 C9 C11 -65.33(16) . . . . ?
C8 P1 C9 C1 178.33(16) . . . . ?
C8 P1 C9 C2AA 52.19(17) . . . . ?
C8 P1 C21 C16 45.26(19) . . . . ?
C8 P1 C21 C0AA 160.17(16) . . . . ?
C8 P1 C21 C1AA -77.9(2) . . . . ?
C8 C4 C5 C6 178.89(16) . . . . ?
C8 C4 C12 N3 -178.15(14) . . . . ?
C8 C4 C12 C15 3.3(2) . . . . ?
C8 C20 C22 C15 1.0(3) . . . . ?
C9 P1 C8 C4 99.28(14) . . . . ?
C9 P1 C8 C20 -81.14(17) . . . . ?
C9 P1 C21 C16 162.35(17) . . . . ?
C9 P1 C21 C0AA -82.74(18) . . . . ?
C9 P1 C21 C1AA 39.2(2) . . . . ?
C10 C17 C18 C14 -0.6(3) . . . . ?
C12 N3 C6 C5 1.21(18) . . . . ?
C12 N3 C6 C10 176.86(14) . . . . ?
C12 C4 C5 C6 -1.13(17) . . . . ?
C12 C4 C8 P1 175.84(12) . . . . ?
C12 C4 C8 C20 -3.8(2) . . . . ?
C12 C15 C22 C20 -1.6(3) . . . . ?
C13 C7 C14 C18 1.0(3) . . . . ?
C13 C7 C14 C3AA -178.77(19) . . . . ?
C13 C10 C17 C18 0.9(3) . . . . ?
C14 C7 C13 C10 -0.7(3) . . . . ?
C17 C10 C13 C7 -0.3(3) . . . . ?
C19 N3 C6 C5 171.84(16) . . . . ?
C19 N3 C6 C10 -12.5(3) . . . . ?
C19 N3 C12 C4 -172.83(16) . . . . ?
C19 N3 C12 C15 5.6(3) . . . . ?
C21 P1 C8 C4 -138.41(13) . . . . ?
C21 P1 C8 C20 41.17(18) . . . . ?
C21 P1 C9 C11 175.56(15) . . . . ?
C21 P1 C9 C1 59.2(2) . . . . ?
C21 P1 C9 C2AA -66.92(19) . . . . ?
C3AA C14 C18 C17 179.39(19) . . . . ?

_olex2_date_sample_data_collection 2020-10-29
_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.599
####################################################################### 
# 
# 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_niuy2_0706
_database_code_depnum_ccdc_archive 'CCDC 2043002'
loop_
_audit_author_name
_audit_author_address
niuuuuu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 Cl N O P'
_chemical_formula_sum            'C23 H29 Cl N O P'
_chemical_formula_weight         401.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.5630(8)
_cell_length_b                   7.9513(2)
_cell_length_c                   17.9128(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.877(2)
_cell_angle_gamma                90
_cell_volume                     4463.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3443
_cell_measurement_temperature    291.76(10)
_cell_measurement_theta_max      69.7310
_cell_measurement_theta_min      8.8740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7520
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        66.577
_diffrn_reflns_theta_max         66.577
_diffrn_reflns_theta_min         4.974
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.76(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     86.00 173.00   1.00    1.00    --  108.00  50.00  90.00   87
  2  ω    152.00 178.00   1.00    1.00    --  108.00  38.00 120.00   26
  3  ω     92.00 145.00   1.00    1.00    --  108.00  38.00 120.00   53
  4  ω     60.00 123.00   1.00    1.00    --  108.00 -38.00 120.00   63
  5  ω     38.00 133.00   1.00    1.00    --  108.00 -77.00 -30.00   95
  6  ω     87.00 153.00   1.00    1.00    --  108.00  63.00-180.00   66
  7  ω    100.00 139.00   1.00    1.00    --  108.00 111.00-180.00   39
  8  ω     57.00 145.00   1.00    1.00    --  108.00 178.00 -90.00   88
  9  ω     30.00  63.00   1.00    1.00    --    0.00  57.00 -60.00   33
 10  ω     -4.00  23.00   1.00    1.00    --    0.00  57.00 -60.00   27
 11  ω     24.00 105.00   1.00    1.00    --   54.00-125.00-120.00   81
 12  ω     24.00  49.00   1.00    1.00    --   54.00-125.00  60.00   25
 13  ω     24.00  62.00   1.00    1.00    --   54.00-125.00 120.00   38
 14  ω    -19.00  17.00   1.00    1.00    --    0.00 -57.00   0.00   36
 15  ω    -57.00 -29.00   1.00    1.00    --    0.00 -57.00   0.00   28
 16  ω    -18.00  57.00   1.00    1.00    --   54.00   0.00-150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0086546000
_diffrn_orient_matrix_UB_12      0.1053499000
_diffrn_orient_matrix_UB_13      -0.0724226000
_diffrn_orient_matrix_UB_21      0.0417400000
_diffrn_orient_matrix_UB_22      0.0979470000
_diffrn_orient_matrix_UB_23      0.0219213000
_diffrn_orient_matrix_UB_31      0.0244544000
_diffrn_orient_matrix_UB_32      -0.1298422000
_diffrn_orient_matrix_UB_33      -0.0422257000
_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                3393
_reflns_number_total             3852
_reflns_odcompleteness_completeness 97.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.065
_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)+(0.0724P)²+1.8174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.14941(2) -0.00312(6) 0.88315(3) 0.03735(16) Uani 1 1 d . . . . .
Cl2 Cl -0.13996(2) -0.52336(7) 0.88213(5) 0.0719(2) Uani 1 1 d . . . . .
O1 O 0.13270(4) -0.17198(17) 0.85907(8) 0.0504(4) Uani 1 1 d . . . . .
N2 N -0.00693(4) 0.14429(19) 0.85441(9) 0.0385(3) Uani 1 1 d . . . . .
C3 C 0.04388(5) -0.0537(2) 0.87676(10) 0.0357(4) Uani 1 1 d . . . . .
H3 H 0.057268 -0.156902 0.886523 0.043 Uiso 1 1 calc R U . . .
C4 C 0.03163(5) 0.2250(2) 0.85484(10) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.06459(5) 0.1037(2) 0.86746(9) 0.0328(4) Uani 1 1 d . . . . .
C6 C -0.03396(5) -0.1472(2) 0.87256(10) 0.0367(4) Uani 1 1 d . . . . .
C7 C -0.09888(6) -0.3786(2) 0.87870(12) 0.0449(4) Uani 1 1 d . . . . .
C8 C 0.10748(5) 0.1553(2) 0.86944(10) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.11497(6) 0.3271(2) 0.86199(11) 0.0471(5) Uani 1 1 d . . . . .
H9 H 0.143010 0.364530 0.864258 0.056 Uiso 1 1 calc R U . . .
C10 C 0.00085(6) -0.0249(2) 0.86871(10) 0.0364(4) Uani 1 1 d . . . . .
C11 C -0.06878(7) -0.3585(3) 0.94006(12) 0.0498(5) Uani 1 1 d . . . . .
H11 H -0.070124 -0.422031 0.983294 0.060 Uiso 1 1 calc R U . . .
C12 C -0.03631(6) -0.2419(2) 0.93667(11) 0.0437(4) Uani 1 1 d . . . . .
H12 H -0.015872 -0.227376 0.978062 0.052 Uiso 1 1 calc R U . . .
C13 C 0.03987(7) 0.3957(2) 0.84697(11) 0.0463(5) Uani 1 1 d . . . . .
H13 H 0.017822 0.473705 0.839142 0.056 Uiso 1 1 calc R U . . .
C14 C -0.09729(6) -0.2879(3) 0.81393(12) 0.0495(5) Uani 1 1 d . . . . .
H14 H -0.117657 -0.304344 0.772589 0.059 Uiso 1 1 calc R U . . .
C15 C -0.06497(6) -0.1718(3) 0.81108(11) 0.0480(5) Uani 1 1 d . . . . .
H15 H -0.063839 -0.109068 0.767550 0.058 Uiso 1 1 calc R U . . .
C16 C 0.08205(7) 0.4447(2) 0.85126(13) 0.0517(5) Uani 1 1 d . . . . .
H16 H 0.088614 0.558008 0.846922 0.062 Uiso 1 1 calc R U . . .
C17 C 0.19286(7) 0.0526(3) 0.82499(13) 0.0568(6) Uani 1 1 d . . . . .
C18 C -0.04808(6) 0.2285(3) 0.85011(14) 0.0541(5) Uani 1 1 d . . . . .
H18A H -0.045571 0.326879 0.881397 0.081 Uiso 1 1 calc R U . . .
H18B H -0.068748 0.153449 0.867088 0.081 Uiso 1 1 calc R U . . .
H18C H -0.057070 0.260719 0.799021 0.081 Uiso 1 1 calc R U . . .
C19 C 0.12824(7) -0.0629(3) 1.02237(13) 0.0601(6) Uani 1 1 d . . . . .
H19A H 0.105120 0.015053 1.011167 0.090 Uiso 1 1 calc R U . . .
H19B H 0.135724 -0.069343 1.075844 0.090 Uiso 1 1 calc R U . . .
H19C H 0.119658 -0.171958 1.003211 0.090 Uiso 1 1 calc R U . . .
C20 C 0.17143(8) 0.0986(4) 0.74665(13) 0.0741(8) Uani 1 1 d . . . . .
H20A H 0.149870 0.016796 0.730580 0.111 Uiso 1 1 calc R U . . .
H20B H 0.192387 0.100117 0.711995 0.111 Uiso 1 1 calc R U . . .
H20C H 0.158547 0.207704 0.748146 0.111 Uiso 1 1 calc R U . . .
C21 C 0.16686(6) -0.0028(3) 0.98556(12) 0.0496(5) Uani 1 1 d . . . . .
C22 C 0.20330(9) -0.1279(5) 1.00470(15) 0.0888(10) Uani 1 1 d . . . . .
H22A H 0.195972 -0.233398 0.980515 0.133 Uiso 1 1 calc R U . . .
H22B H 0.208009 -0.144014 1.058165 0.133 Uiso 1 1 calc R U . . .
H22C H 0.228825 -0.084710 0.987455 0.133 Uiso 1 1 calc R U . . .
C23 C 0.17939(8) 0.1712(4) 1.01742(14) 0.0734(7) Uani 1 1 d . . . . .
H23A H 0.205258 0.207171 0.998999 0.110 Uiso 1 1 calc R U . . .
H23B H 0.183776 0.165704 1.071331 0.110 Uiso 1 1 calc R U . . .
H23C H 0.157002 0.249985 1.001919 0.110 Uiso 1 1 calc R U . . .
C24 C 0.21840(9) -0.1114(5) 0.81756(18) 0.0925(10) Uani 1 1 d . . . . .
H24A H 0.233736 -0.139712 0.865446 0.139 Uiso 1 1 calc R U . . .
H24B H 0.238205 -0.095219 0.781489 0.139 Uiso 1 1 calc R U . . .
H24C H 0.199098 -0.200902 0.801133 0.139 Uiso 1 1 calc R U . . .
C25 C 0.22349(8) 0.1910(5) 0.85507(17) 0.0903(10) Uani 1 1 d . . . . .
H25A H 0.207852 0.293082 0.860147 0.136 Uiso 1 1 calc R U . . .
H25B H 0.244225 0.208820 0.820794 0.136 Uiso 1 1 calc R U . . .
H25C H 0.237738 0.158482 0.903277 0.136 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4873(14) . ?
P1 C8 1.8223(18) . ?
P1 C17 1.872(2) . ?
P1 C21 1.851(2) . ?
Cl2 C7 1.7406(19) . ?
N2 C4 1.375(2) . ?
N2 C10 1.386(2) . ?
N2 C18 1.455(2) . ?
C3 H3 0.9300 . ?
C3 C5 1.431(2) . ?
C3 C10 1.368(2) . ?
C4 C5 1.417(2) . ?
C4 C13 1.392(3) . ?
C5 C8 1.411(2) . ?
C6 C10 1.475(2) . ?
C6 C12 1.383(3) . ?
C6 C15 1.397(3) . ?
C7 C11 1.373(3) . ?
C7 C14 1.372(3) . ?
C8 C9 1.395(3) . ?
C9 H9 0.9300 . ?
C9 C16 1.394(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C16 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.527(3) . ?
C17 C24 1.546(4) . ?
C17 C25 1.521(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 C21 1.530(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.528(3) . ?
C21 C23 1.531(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C8 111.02(8) . . ?
O1 P1 C17 108.05(10) . . ?
O1 P1 C21 109.99(10) . . ?
C8 P1 C17 109.27(10) . . ?
C8 P1 C21 104.93(9) . . ?
C21 P1 C17 113.59(10) . . ?
C4 N2 C10 108.37(14) . . ?
C4 N2 C18 124.70(16) . . ?
C10 N2 C18 126.42(16) . . ?
C5 C3 H3 126.2 . . ?
C10 C3 H3 126.2 . . ?
C10 C3 C5 107.65(15) . . ?
N2 C4 C5 108.38(15) . . ?
N2 C4 C13 129.08(17) . . ?
C13 C4 C5 122.51(17) . . ?
C4 C5 C3 106.10(15) . . ?
C8 C5 C3 134.58(16) . . ?
C8 C5 C4 119.31(16) . . ?
C12 C6 C10 120.81(16) . . ?
C12 C6 C15 118.45(17) . . ?
C15 C6 C10 120.74(17) . . ?
C11 C7 Cl2 119.71(16) . . ?
C14 C7 Cl2 118.71(16) . . ?
C14 C7 C11 121.58(18) . . ?
C5 C8 P1 118.76(13) . . ?
C9 C8 P1 124.13(14) . . ?
C9 C8 C5 117.10(16) . . ?
C8 C9 H9 118.7 . . ?
C16 C9 C8 122.53(18) . . ?
C16 C9 H9 118.7 . . ?
N2 C10 C6 122.14(15) . . ?
C3 C10 N2 109.47(16) . . ?
C3 C10 C6 128.38(17) . . ?
C7 C11 H11 120.5 . . ?
C7 C11 C12 119.09(18) . . ?
C12 C11 H11 120.5 . . ?
C6 C12 C11 120.88(18) . . ?
C6 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C4 C13 H13 121.3 . . ?
C16 C13 C4 117.38(18) . . ?
C16 C13 H13 121.3 . . ?
C7 C14 H14 120.5 . . ?
C7 C14 C15 118.98(19) . . ?
C15 C14 H14 120.5 . . ?
C6 C15 H15 119.5 . . ?
C14 C15 C6 121.02(18) . . ?
C14 C15 H15 119.5 . . ?
C9 C16 H16 119.4 . . ?
C13 C16 C9 121.10(18) . . ?
C13 C16 H16 119.4 . . ?
C20 C17 P1 107.12(14) . . ?
C20 C17 C24 107.5(2) . . ?
C24 C17 P1 105.82(18) . . ?
C25 C17 P1 116.81(17) . . ?
C25 C17 C20 110.2(2) . . ?
C25 C17 C24 109.0(2) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C19 H19A 109.5 . . ?
C21 C19 H19B 109.5 . . ?
C21 C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 P1 105.59(15) . . ?
C19 C21 C23 107.77(19) . . ?
C22 C21 P1 110.37(16) . . ?
C22 C21 C19 108.5(2) . . ?
C22 C21 C23 110.5(2) . . ?
C23 C21 P1 113.82(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 C25 H25A 109.5 . . ?
C17 C25 H25B 109.5 . . ?
C17 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C9 C16 179.74(16) . . . . ?
Cl2 C7 C11 C12 -179.67(15) . . . . ?
Cl2 C7 C14 C15 179.46(16) . . . . ?
O1 P1 C8 C5 23.89(16) . . . . ?
O1 P1 C8 C9 -157.32(16) . . . . ?
O1 P1 C17 C20 74.4(2) . . . . ?
O1 P1 C17 C24 -40.07(19) . . . . ?
O1 P1 C17 C25 -161.5(2) . . . . ?
O1 P1 C21 C19 -54.81(17) . . . . ?
O1 P1 C21 C22 62.2(2) . . . . ?
O1 P1 C21 C23 -172.81(15) . . . . ?
N2 C4 C5 C3 -1.62(19) . . . . ?
N2 C4 C5 C8 179.21(15) . . . . ?
N2 C4 C13 C16 178.52(18) . . . . ?
C3 C5 C8 P1 2.8(3) . . . . ?
C3 C5 C8 C9 -176.09(19) . . . . ?
C4 N2 C10 C3 -1.2(2) . . . . ?
C4 N2 C10 C6 179.63(15) . . . . ?
C4 C5 C8 P1 -178.33(13) . . . . ?
C4 C5 C8 C9 2.8(2) . . . . ?
C4 C13 C16 C9 0.9(3) . . . . ?
C5 C3 C10 N2 0.2(2) . . . . ?
C5 C3 C10 C6 179.27(17) . . . . ?
C5 C4 C13 C16 0.6(3) . . . . ?
C5 C8 C9 C16 -1.4(3) . . . . ?
C7 C11 C12 C6 -0.2(3) . . . . ?
C7 C14 C15 C6 0.6(3) . . . . ?
C8 P1 C17 C20 -46.5(2) . . . . ?
C8 P1 C17 C24 -160.98(17) . . . . ?
C8 P1 C17 C25 77.6(2) . . . . ?
C8 P1 C21 C19 64.66(17) . . . . ?
C8 P1 C21 C22 -178.28(19) . . . . ?
C8 P1 C21 C23 -53.34(17) . . . . ?
C8 C9 C16 C13 -0.4(3) . . . . ?
C10 N2 C4 C5 1.75(19) . . . . ?
C10 N2 C4 C13 -176.44(19) . . . . ?
C10 C3 C5 C4 0.9(2) . . . . ?
C10 C3 C5 C8 179.87(18) . . . . ?
C10 C6 C12 C11 -179.24(18) . . . . ?
C10 C6 C15 C14 179.03(18) . . . . ?
C11 C7 C14 C15 -1.1(3) . . . . ?
C12 C6 C10 N2 -121.9(2) . . . . ?
C12 C6 C10 C3 59.1(3) . . . . ?
C12 C6 C15 C14 0.0(3) . . . . ?
C13 C4 C5 C3 176.72(18) . . . . ?
C13 C4 C5 C8 -2.5(3) . . . . ?
C14 C7 C11 C12 0.8(3) . . . . ?
C15 C6 C10 N2 59.1(2) . . . . ?
C15 C6 C10 C3 -119.9(2) . . . . ?
C15 C6 C12 C11 -0.2(3) . . . . ?
C17 P1 C8 C5 142.97(14) . . . . ?
C17 P1 C8 C9 -38.23(19) . . . . ?
C17 P1 C21 C19 -176.06(15) . . . . ?
C17 P1 C21 C22 -59.0(2) . . . . ?
C17 P1 C21 C23 65.94(19) . . . . ?
C18 N2 C4 C5 173.94(17) . . . . ?
C18 N2 C4 C13 -4.2(3) . . . . ?
C18 N2 C10 C3 -173.22(18) . . . . ?
C18 N2 C10 C6 7.6(3) . . . . ?
C21 P1 C8 C5 -94.89(15) . . . . ?
C21 P1 C8 C9 83.91(18) . . . . ?
C21 P1 C17 C20 -163.26(18) . . . . ?
C21 P1 C17 C24 82.25(19) . . . . ?
C21 P1 C17 C25 -39.2(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 1.480
_oxdiff_exptl_absorpt_empirical_full_min 0.675
####################################################################### 
# 
# 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_niuy_0902
_audit_block_doi                 10.5517/ccdc.csd.cc26kx7y
_database_code_depnum_ccdc_archive 'CCDC 2043000'
loop_
_audit_author_name
_audit_author_address
niuuu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-04
_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         'C21 H18 N O P'
_chemical_formula_sum            'C21 H18 N O P'
_chemical_formula_weight         331.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.7400(3)
_cell_length_b                   11.2344(5)
_cell_length_c                   17.1171(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.056(3)
_cell_angle_gamma                90
_cell_volume                     1676.50(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2781
_cell_measurement_temperature    292.19(10)
_cell_measurement_theta_max      69.8150
_cell_measurement_theta_min      7.7690
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6054
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         4.712
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.19(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  62.00   1.00    1.00    --   54.00  77.00  60.00   34
  2  ω     86.00 178.00   1.00    1.00    --  108.00  50.00  90.00   92
  3  ω     81.00 177.00   1.00    1.00    --  108.00  77.00 120.00   96
  4  ω     75.00 114.00   1.00    1.00    --   54.00  57.00 -60.00   39
  5  ω     81.00 125.00   1.00    1.00    --  108.00 -50.00-180.00   44
  6  ω     40.00 124.00   1.00    1.00    --  108.00 -63.00   0.00   84
  7  ω     91.00 116.00   1.00    1.00    --  108.00-111.00   0.00   25
  8  ω     47.00  79.00   1.00    1.00    --  108.00-111.00   0.00   32
  9  ω     23.00  70.00   1.00    1.00    --   54.00 -57.00 -60.00   47
 10  ω     19.00  66.00   1.00    1.00    --    0.00  57.00-180.00   47
 11  ω    -15.00  14.00   1.00    1.00    --    0.00  57.00-180.00   29
 12  ω    -14.00  57.00   1.00    1.00    --   54.00 -57.00-120.00   71
 13  ω    -18.00  71.00   1.00    1.00    --   54.00 -38.00  30.00   89
 14  ω     38.00 102.00   1.00    1.00    --  108.00  12.00 120.00   64
 15  ω     47.00 117.00   1.00    1.00    --  108.00 -63.00 150.00   70
 16  ω    -29.00   2.00   1.00    1.00    --    0.00  88.00   4.00   31
 17  ω    -38.00 -13.00   1.00    1.00    --    0.00 -57.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1259644000
_diffrn_orient_matrix_UB_12      -0.0693218000
_diffrn_orient_matrix_UB_13      -0.0483116000
_diffrn_orient_matrix_UB_21      -0.0027216000
_diffrn_orient_matrix_UB_22      -0.0935073000
_diffrn_orient_matrix_UB_23      0.0657223000
_diffrn_orient_matrix_UB_31      -0.1239074000
_diffrn_orient_matrix_UB_32      0.0724883000
_diffrn_orient_matrix_UB_33      0.0385659000
_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                2635
_reflns_number_total             2957
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.052
_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)+(0.0511P)²+0.4482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C3(H3), C12(H12), C13(H13), C18(H18), C8(H8), C11(H11), C19(H19),
 C7(H7), C21(H21), C4(H4), C14(H14), C15(H15), C2(H2), C20(H20)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.25681(4) 0.11383(4) 0.17203(2) 0.03077(15) Uani 1 1 d . . . . .
O1 O 0.34604(14) 0.11978(11) 0.24930(6) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.10213(19) 0.40086(13) -0.05152(9) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.2077(2) 0.38934(14) 0.01126(10) 0.0369(4) Uani 1 1 d . . . . .
C17 C -0.0256(2) 0.19413(18) 0.20946(11) 0.0468(4) Uani 1 1 d . . . . .
H17 H 0.023477 0.267344 0.215592 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4106(2) 0.43626(18) 0.10545(11) 0.0491(5) Uani 1 1 d . . . . .
H3 H 0.486430 0.488056 0.125651 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3535(2) -0.11854(17) -0.00322(11) 0.0490(5) Uani 1 1 d . . . . .
H12 H 0.336018 -0.125859 -0.057231 0.059 Uiso 1 1 calc R U . . .
C10 C 0.31938(17) -0.01047(14) 0.11560(9) 0.0313(3) Uani 1 1 d . . . . .
C13 C 0.4381(2) -0.20424(17) 0.03834(12) 0.0480(5) Uani 1 1 d . . . . .
H13 H 0.478332 -0.268436 0.012278 0.058 Uiso 1 1 calc R U . . .
C16 C 0.05364(18) 0.09668(15) 0.18277(9) 0.0329(4) Uani 1 1 d . . . . .
C18 C -0.1764(2) 0.1828(2) 0.22688(12) 0.0569(5) Uani 1 1 d . . . . .
H18 H -0.228716 0.248464 0.244675 0.068 Uiso 1 1 calc R U . . .
C6 C 0.17940(18) 0.27947(14) 0.04888(9) 0.0325(3) Uani 1 1 d . . . . .
C9 C 0.0976(3) 0.49724(19) -0.10878(11) 0.0608(6) Uani 1 1 d . . . . .
H9A H 0.178336 0.486399 -0.143329 0.091 Uiso 1 1 calc R U . . .
H9B H 0.111097 0.572060 -0.082085 0.091 Uiso 1 1 calc R U . . .
H9C H 0.000348 0.496682 -0.138607 0.091 Uiso 1 1 calc R U . . .
C8 C 0.0086(2) 0.30359(17) -0.05371(10) 0.0473(4) Uani 1 1 d . . . . .
H8 H -0.072565 0.290883 -0.090903 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2947(2) -0.02206(17) 0.03461(10) 0.0421(4) Uani 1 1 d . . . . .
H11 H 0.238426 0.035400 0.005971 0.051 Uiso 1 1 calc R U . . .
C5 C 0.27469(17) 0.24822(14) 0.11602(9) 0.0313(3) Uani 1 1 d . . . . .
C19 C -0.2503(2) 0.0745(2) 0.21801(12) 0.0586(6) Uani 1 1 d . . . . .
H19 H -0.351612 0.066821 0.230546 0.070 Uiso 1 1 calc R U . . .
C7 C 0.0502(2) 0.22777(16) 0.00592(10) 0.0414(4) Uani 1 1 d . . . . .
H7 H 0.003366 0.155854 0.016685 0.050 Uiso 1 1 calc R U . . .
C21 C -0.02180(19) -0.01160(17) 0.17289(10) 0.0429(4) Uani 1 1 d . . . . .
H21 H 0.029364 -0.077270 0.154362 0.051 Uiso 1 1 calc R U . . .
C4 C 0.38863(19) 0.32737(16) 0.14280(10) 0.0404(4) Uani 1 1 d . . . . .
H4 H 0.452098 0.307493 0.186767 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4628(2) -0.19462(17) 0.11823(12) 0.0504(5) Uani 1 1 d . . . . .
H14 H 0.518615 -0.252744 0.146511 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4042(2) -0.09779(16) 0.15650(10) 0.0425(4) Uani 1 1 d . . . . .
H15 H 0.422033 -0.091185 0.210535 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3215(2) 0.46749(16) 0.03929(11) 0.0467(5) Uani 1 1 d . . . . .
H2 H 0.337116 0.539232 0.013939 0.056 Uiso 1 1 calc R U . . .
C20 C -0.1737(2) -0.0216(2) 0.19070(12) 0.0559(5) Uani 1 1 d . . . . .
H20 H -0.224035 -0.094280 0.184043 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4886(11) . ?
P1 C10 1.8047(16) . ?
P1 C16 1.8084(16) . ?
P1 C5 1.8012(16) . ?
N1 C1 1.372(2) . ?
N1 C9 1.459(2) . ?
N1 C8 1.364(3) . ?
C1 C6 1.422(2) . ?
C1 C2 1.387(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.390(2) . ?
C17 C18 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.400(3) . ?
C3 C2 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C12 C11 1.380(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.389(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C16 C21 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C6 C5 1.415(2) . ?
C6 C7 1.427(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C7 1.359(2) . ?
C11 H11 0.9300 . ?
C5 C4 1.389(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(3) . ?
C7 H7 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.388(3) . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C10 110.53(7) . . ?
O1 P1 C16 111.77(7) . . ?
O1 P1 C5 112.06(7) . . ?
C10 P1 C16 107.99(7) . . ?
C5 P1 C10 108.83(7) . . ?
C5 P1 C16 105.44(7) . . ?
C1 N1 C9 125.52(17) . . ?
C8 N1 C1 108.34(14) . . ?
C8 N1 C9 126.04(17) . . ?
N1 C1 C6 107.92(15) . . ?
N1 C1 C2 129.60(16) . . ?
C2 C1 C6 122.43(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.34(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.77(17) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.63(17) . . ?
C11 C12 H12 119.7 . . ?
C11 C10 P1 124.97(13) . . ?
C15 C10 P1 116.61(12) . . ?
C15 C10 C11 118.35(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.94(18) . . ?
C14 C13 H13 120.0 . . ?
C17 C16 P1 117.71(13) . . ?
C21 C16 P1 122.84(13) . . ?
C21 C16 C17 119.14(15) . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.28(19) . . ?
C19 C18 H18 119.9 . . ?
C1 C6 C7 106.06(14) . . ?
C5 C6 C1 118.16(14) . . ?
C5 C6 C7 135.76(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 H8 124.6 . . ?
C7 C8 N1 110.70(16) . . ?
C7 C8 H8 124.6 . . ?
C12 C11 C10 120.22(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C6 C5 P1 124.89(12) . . ?
C4 C5 P1 116.63(13) . . ?
C4 C5 C6 118.45(15) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.78(17) . . ?
C20 C19 H19 120.1 . . ?
C6 C7 H7 126.5 . . ?
C8 C7 C6 106.97(16) . . ?
C8 C7 H7 126.5 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.87(18) . . ?
C20 C21 H21 120.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.82(16) . . ?
C5 C4 H4 119.1 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.65(17) . . ?
C15 C14 H14 120.2 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.20(16) . . ?
C14 C15 H15 119.4 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.33(17) . . ?
C3 C2 H2 120.8 . . ?
C19 C20 C21 120.57(19) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 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
P1 C10 C11 C12 177.11(14) . . . . ?
P1 C10 C15 C14 -177.47(14) . . . . ?
P1 C16 C21 C20 172.61(14) . . . . ?
P1 C5 C4 C3 -178.14(13) . . . . ?
O1 P1 C10 C11 -160.03(14) . . . . ?
O1 P1 C10 C15 16.98(15) . . . . ?
O1 P1 C16 C17 71.71(15) . . . . ?
O1 P1 C16 C21 -101.90(15) . . . . ?
O1 P1 C5 C6 -165.78(13) . . . . ?
O1 P1 C5 C4 12.49(15) . . . . ?
N1 C1 C6 C5 -179.79(13) . . . . ?
N1 C1 C6 C7 -0.97(17) . . . . ?
N1 C1 C2 C3 178.06(17) . . . . ?
N1 C8 C7 C6 -0.3(2) . . . . ?
C1 N1 C8 C7 -0.3(2) . . . . ?
C1 C6 C5 P1 179.64(11) . . . . ?
C1 C6 C5 C4 1.4(2) . . . . ?
C1 C6 C7 C8 0.80(19) . . . . ?
C17 C16 C21 C20 -0.9(3) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C10 P1 C16 C17 -166.50(13) . . . . ?
C10 P1 C16 C21 19.89(16) . . . . ?
C10 P1 C5 C6 71.67(14) . . . . ?
C10 P1 C5 C4 -110.06(13) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C16 P1 C10 C11 77.42(16) . . . . ?
C16 P1 C10 C15 -105.57(13) . . . . ?
C16 P1 C5 C6 -43.97(15) . . . . ?
C16 P1 C5 C4 134.30(13) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C16 C21 C20 C19 0.0(3) . . . . ?
C18 C17 C16 P1 -172.97(15) . . . . ?
C18 C17 C16 C21 0.9(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C9 N1 C1 C6 -175.66(16) . . . . ?
C9 N1 C1 C2 6.7(3) . . . . ?
C9 N1 C8 C7 176.15(17) . . . . ?
C8 N1 C1 C6 0.78(18) . . . . ?
C8 N1 C1 C2 -176.91(18) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C5 P1 C10 C11 -36.57(16) . . . . ?
C5 P1 C10 C15 140.45(13) . . . . ?
C5 P1 C16 C17 -50.29(14) . . . . ?
C5 P1 C16 C21 136.10(14) . . . . ?
C5 C6 C7 C8 179.31(18) . . . . ?
C7 C6 C5 P1 1.3(3) . . . . ?
C7 C6 C5 C4 -176.97(18) . . . . ?
C4 C3 C2 C1 1.1(3) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
C2 C1 C6 C7 176.92(16) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?

_olex2_date_sample_data_collection 2020-09-02
_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 2.327
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_niuy_0901
_audit_block_doi                 10.5517/ccdc.csd.cc26kx6x
_database_code_depnum_ccdc_archive 'CCDC 2042999'
loop_
_audit_author_name
_audit_author_address
niuyniu
;lan zhou university
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;
_audit_creation_date             2020-09-04
_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         '2(C17 H26 N O P)'
_chemical_formula_sum            'C34 H52 N2 O2 P2'
_chemical_formula_weight         582.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9412(2)
_cell_length_b                   13.9538(6)
_cell_length_c                   16.5476(8)
_cell_angle_alpha                112.708(4)
_cell_angle_beta                 90.345(3)
_cell_angle_gamma                96.480(3)
_cell_volume                     1678.23(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5595
_cell_measurement_temperature    292.65(10)
_cell_measurement_theta_max      69.9410
_cell_measurement_theta_min      5.4720
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10903
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.546
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    148.00 173.00   1.00    1.00    --  108.00  38.00   0.00   25
  2  ω    108.00 164.00   1.00    1.00    --  108.00 111.00 -90.00   56
  3  ω    101.00 143.00   1.00    1.00    --  108.00 111.00 -60.00   42
  4  ω     96.00 150.00   1.00    1.00    --  108.00  63.00 -90.00   54
  5  ω     92.00 140.00   1.00    1.00    --  108.00 -25.00-120.00   48
  6  ω     85.00 121.00   1.00    1.00    --  108.00  38.00   0.00   36
  7  ω     75.00 147.00   1.00    1.00    --  108.00  25.00  90.00   72
  8  ω     75.00 111.00   1.00    1.00    --   54.00  57.00  60.00   36
  9  ω     79.00 130.00   1.00    1.00    --  108.00 -25.00 120.00   51
 10  ω     87.00 113.00   1.00    1.00    --  108.00-111.00  30.00   26
 11  ω     74.00 113.00   1.00    1.00    --  108.00-111.00 -90.00   39
 12  ω     48.00 111.00   1.00    1.00    --  108.00 -50.00   0.00   63
 13  ω     52.00  78.00   1.00    1.00    --  108.00-111.00  30.00   26
 14  ω     36.00 113.00   1.00    1.00    --  108.00-111.00 150.00   77
 15  ω     43.00  71.00   1.00    1.00    --  108.00 -25.00 120.00   28
 16  ω     45.00 130.00   1.00    1.00    --  108.00 -63.00 150.00   85
 17  ω     35.00 120.00   1.00    1.00    --   54.00  38.00  30.00   85
 18  ω     39.00 107.00   1.00    1.00    --   54.00  57.00 -90.00   68
 19  ω     35.00  77.00   1.00    1.00    --  108.00 -25.00-120.00   42
 20  ω     45.00 136.00   1.00    1.00    --  108.00 -77.00 -90.00   91
 21  ω     32.00  63.00   1.00    1.00    --    0.00  57.00  30.00   31
 22  ω    -13.00  22.00   1.00    1.00    --    0.00  57.00  30.00   35
 23  ω    -18.00  78.00   1.00    1.00    --   54.00 -38.00  90.00   96
 24  ω     13.00  71.00   1.00    1.00    --   54.00-105.00  81.00   58
 25  ω     14.00  71.00   1.00    1.00    --   54.00 -57.00 -90.00   57
 26  ω     23.00 108.00   1.00    1.00    --   54.00-125.00-120.00   85
 27  ω     -9.00  18.00   1.00    1.00    --    0.00 -57.00-120.00   27
 28  ω     87.00 136.00   1.00    1.00    --  108.00 178.00-180.00   49
 29  ω    -18.00   7.00   1.00    1.00    --    0.00  57.00-180.00   25
 30  ω    -58.00 -25.00   1.00    1.00    --    0.00 -57.00-120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0168600000
_diffrn_orient_matrix_UB_12      0.0533105000
_diffrn_orient_matrix_UB_13      -0.0651473000
_diffrn_orient_matrix_UB_21      0.0604924000
_diffrn_orient_matrix_UB_22      0.1072599000
_diffrn_orient_matrix_UB_23      0.0734050000
_diffrn_orient_matrix_UB_31      0.1851714000
_diffrn_orient_matrix_UB_32      -0.0142813000
_diffrn_orient_matrix_UB_33      -0.0241385000
_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                5335
_reflns_number_total             5924
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.042
_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)+(0.0762P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C3(H3), C2(H2), C8(H8), C21(H21), C19(H19), C25(H25),
 C20(H20), C24(H24)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C9(H9A,H9B,
 H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C26(H26A,
 H26B,H26C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C33(H33A,H33B,H33C),
 C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.76207(5) 0.05480(3) 0.20981(3) 0.03675(14) Uani 1 1 d . . . . .
O1 O 0.7813(2) -0.05378(11) 0.15085(9) 0.0611(4) Uani 1 1 d . . . . .
N1 N 1.13667(19) -0.03374(13) 0.41156(10) 0.0455(4) Uani 1 1 d . . . . .
C13 C 0.5129(3) -0.0259(2) 0.2820(2) 0.0838(8) Uani 1 1 d . . . . .
H13A H 0.537336 -0.090494 0.237474 0.126 Uiso 1 1 calc R U . . .
H13B H 0.396676 -0.033192 0.296714 0.126 Uiso 1 1 calc R U . . .
H13C H 0.586000 -0.009036 0.333299 0.126 Uiso 1 1 calc R U . . .
C11 C 0.4180(3) 0.0330(3) 0.1688(2) 0.0927(10) Uani 1 1 d . . . . .
H11A H 0.420008 0.091206 0.151313 0.139 Uiso 1 1 calc R U . . .
H11B H 0.305523 0.016071 0.184340 0.139 Uiso 1 1 calc R U . . .
H11C H 0.450136 -0.026430 0.120993 0.139 Uiso 1 1 calc R U . . .
C1 C 1.0836(2) 0.05384(14) 0.40573(11) 0.0388(4) Uani 1 1 d . . . . .
C4 C 0.9368(3) 0.20008(14) 0.36714(13) 0.0484(4) Uani 1 1 d . . . . .
H4 H 0.888317 0.251398 0.355562 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5119(4) 0.1645(2) 0.3194(2) 0.0969(10) Uani 1 1 d . . . . .
H12A H 0.583733 0.177802 0.370381 0.145 Uiso 1 1 calc R U . . .
H12B H 0.395211 0.160803 0.334067 0.145 Uiso 1 1 calc R U . . .
H12C H 0.537179 0.220160 0.299144 0.145 Uiso 1 1 calc R U . . .
C6 C 0.97493(19) 0.02041(13) 0.32897(10) 0.0336(3) Uani 1 1 d . . . . .
C5 C 0.8992(2) 0.09655(13) 0.30901(11) 0.0357(4) Uani 1 1 d . . . . .
C7 C 0.9665(2) -0.09084(14) 0.28948(12) 0.0411(4) Uani 1 1 d . . . . .
H7 H 0.904781 -0.135119 0.238140 0.049 Uiso 1 1 calc R U . . .
C9 C 1.2553(3) -0.0336(2) 0.47846(15) 0.0617(6) Uani 1 1 d . . . . .
H9A H 1.368049 -0.010672 0.467242 0.093 Uiso 1 1 calc R U . . .
H9B H 1.250729 -0.103041 0.477489 0.093 Uiso 1 1 calc R U . . .
H9C H 1.225693 0.013153 0.534989 0.093 Uiso 1 1 calc R U . . .
C3 C 1.0440(3) 0.23046(15) 0.44211(13) 0.0544(5) Uani 1 1 d . . . . .
H3 H 1.065074 0.300894 0.478999 0.065 Uiso 1 1 calc R U . . .
C2 C 1.1192(2) 0.15783(16) 0.46233(12) 0.0491(5) Uani 1 1 d . . . . .
H2 H 1.191241 0.177798 0.512124 0.059 Uiso 1 1 calc R U . . .
C8 C 1.0659(2) -0.11986(15) 0.34124(13) 0.0482(4) Uani 1 1 d . . . . .
H8 H 1.083227 -0.188460 0.330372 0.058 Uiso 1 1 calc R U . . .
C16 C 0.7659(4) 0.2524(2) 0.1897(2) 0.0781(8) Uani 1 1 d . . . . .
H16A H 0.644200 0.245332 0.184772 0.117 Uiso 1 1 calc R U . . .
H16B H 0.812108 0.292746 0.157514 0.117 Uiso 1 1 calc R U . . .
H16C H 0.804159 0.287292 0.250302 0.117 Uiso 1 1 calc R U . . .
C17 C 1.0218(3) 0.1559(3) 0.1529(2) 0.0942(10) Uani 1 1 d . . . . .
H17A H 1.067346 0.195763 0.211825 0.141 Uiso 1 1 calc R U . . .
H17B H 1.059464 0.191711 0.115858 0.141 Uiso 1 1 calc R U . . .
H17C H 1.060252 0.088084 0.131821 0.141 Uiso 1 1 calc R U . . .
C15 C 0.7558(4) 0.0875(3) 0.05705(16) 0.0887(9) Uani 1 1 d . . . . .
H15A H 0.788727 0.018314 0.032985 0.133 Uiso 1 1 calc R U . . .
H15B H 0.800449 0.126236 0.023277 0.133 Uiso 1 1 calc R U . . .
H15C H 0.634210 0.083115 0.055170 0.133 Uiso 1 1 calc R U . . .
C10 C 0.5426(2) 0.06185(16) 0.24783(14) 0.0504(5) Uani 1 1 d . . . . .
C14 C 0.8256(3) 0.14310(19) 0.15187(14) 0.0563(5) Uani 1 1 d . . . . .
P2 P 0.31288(6) 0.57305(3) 0.27205(3) 0.04049(14) Uani 1 1 d . . . . .
O2 O 0.18743(17) 0.64747(10) 0.27989(9) 0.0524(4) Uani 1 1 d . . . . .
N2 N -0.0486(2) 0.34622(14) -0.00171(11) 0.0565(4) Uani 1 1 d . . . . .
C21 C 0.4030(3) 0.39230(16) 0.13701(15) 0.0598(5) Uani 1 1 d . . . . .
H21 H 0.503947 0.404613 0.170239 0.072 Uiso 1 1 calc R U . . .
C22 C 0.2817(2) 0.46054(14) 0.16820(12) 0.0448(4) Uani 1 1 d . . . . .
C31 C 0.2790(3) 0.51996(15) 0.35844(14) 0.0522(5) Uani 1 1 d . . . . .
C26 C -0.1200(4) 0.2696(2) -0.08651(15) 0.0804(8) Uani 1 1 d . . . . .
H26A H -0.095521 0.296620 -0.131005 0.121 Uiso 1 1 calc R U . . .
H26B H -0.240672 0.256004 -0.084029 0.121 Uiso 1 1 calc R U . . .
H26C H -0.070736 0.205748 -0.100291 0.121 Uiso 1 1 calc R U . . .
C29 C 0.5286(3) 0.75519(17) 0.34537(17) 0.0679(6) Uani 1 1 d . . . . .
H29A H 0.434550 0.784137 0.330665 0.102 Uiso 1 1 calc R U . . .
H29B H 0.632604 0.796930 0.344283 0.102 Uiso 1 1 calc R U . . .
H29C H 0.517170 0.754899 0.402998 0.102 Uiso 1 1 calc R U . . .
C23 C 0.1300(2) 0.43992(13) 0.11628(11) 0.0409(4) Uani 1 1 d . . . . .
C19 C 0.2311(3) 0.28335(15) 0.00552(13) 0.0589(6) Uani 1 1 d . . . . .
H19 H 0.214499 0.225565 -0.047453 0.071 Uiso 1 1 calc R U . . .
C28 C 0.5609(4) 0.6465(2) 0.18805(18) 0.0765(7) Uani 1 1 d . . . . .
H28A H 0.576748 0.578107 0.146426 0.115 Uiso 1 1 calc R U . . .
H28B H 0.660297 0.694618 0.192401 0.115 Uiso 1 1 calc R U . . .
H28C H 0.464413 0.669582 0.168971 0.115 Uiso 1 1 calc R U . . .
C25 C -0.1238(3) 0.43010(18) 0.05153(14) 0.0573(5) Uani 1 1 d . . . . .
H25 H -0.230324 0.444944 0.039843 0.069 Uiso 1 1 calc R U . . .
C20 C 0.3776(3) 0.30559(17) 0.05704(16) 0.0662(6) Uani 1 1 d . . . . .
H20 H 0.462194 0.262063 0.038432 0.079 Uiso 1 1 calc R U . . .
C33 C 0.3737(4) 0.4263(2) 0.34838(19) 0.0802(8) Uani 1 1 d . . . . .
H33A H 0.339899 0.370186 0.292941 0.120 Uiso 1 1 calc R U . . .
H33B H 0.346727 0.403211 0.394956 0.120 Uiso 1 1 calc R U . . .
H33C H 0.493793 0.446873 0.350947 0.120 Uiso 1 1 calc R U . . .
C27 C 0.5308(3) 0.64199(16) 0.27808(14) 0.0535(5) Uani 1 1 d . . . . .
C32 C 0.3231(3) 0.6074(2) 0.44968(15) 0.0695(6) Uani 1 1 d . . . . .
H32A H 0.443984 0.625278 0.458332 0.104 Uiso 1 1 calc R U . . .
H32B H 0.281282 0.583601 0.493892 0.104 Uiso 1 1 calc R U . . .
H32C H 0.271374 0.667979 0.453755 0.104 Uiso 1 1 calc R U . . .
C30 C 0.6778(3) 0.5958(2) 0.30551(19) 0.0724(7) Uani 1 1 d . . . . .
H30A H 0.660595 0.595622 0.362837 0.109 Uiso 1 1 calc R U . . .
H30B H 0.783165 0.637554 0.306623 0.109 Uiso 1 1 calc R U . . .
H30C H 0.681246 0.525356 0.264168 0.109 Uiso 1 1 calc R U . . .
C34 C 0.0872(3) 0.4842(2) 0.35146(18) 0.0743(7) Uani 1 1 d . . . . .
H34A H 0.026260 0.542880 0.360691 0.111 Uiso 1 1 calc R U . . .
H34B H 0.059760 0.456296 0.395132 0.111 Uiso 1 1 calc R U . . .
H34C H 0.055901 0.431163 0.294211 0.111 Uiso 1 1 calc R U . . .
C18 C 0.1085(3) 0.35064(14) 0.03566(12) 0.0471(4) Uani 1 1 d . . . . .
C24 C -0.0214(2) 0.48871(15) 0.12379(13) 0.0473(4) Uani 1 1 d . . . . .
H24 H -0.045222 0.549160 0.169533 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4776(14) . ?
P1 C5 1.8211(17) . ?
P1 C10 1.857(2) . ?
P1 C14 1.863(2) . ?
N1 C1 1.374(2) . ?
N1 C9 1.448(2) . ?
N1 C8 1.369(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C10 1.532(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C10 1.530(3) . ?
C1 C6 1.419(2) . ?
C1 C2 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C4 C3 1.394(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C10 1.512(3) . ?
C6 C5 1.419(2) . ?
C6 C7 1.426(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.361(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.375(3) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C14 1.541(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C14 1.547(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C14 1.524(3) . ?
P2 O2 1.4896(13) . ?
P2 C22 1.8175(18) . ?
P2 C31 1.855(2) . ?
P2 C27 1.865(2) . ?
N2 C26 1.459(3) . ?
N2 C25 1.368(3) . ?
N2 C18 1.374(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(3) . ?
C21 C20 1.400(3) . ?
C22 C23 1.411(3) . ?
C31 C33 1.535(3) . ?
C31 C32 1.538(3) . ?
C31 C34 1.538(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C29 C27 1.544(3) . ?
C23 C18 1.424(2) . ?
C23 C24 1.430(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.371(3) . ?
C19 C18 1.389(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28 C27 1.534(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.357(3) . ?
C20 H20 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C27 C30 1.541(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C5 110.85(8) . . ?
O1 P1 C10 109.91(10) . . ?
O1 P1 C14 108.69(10) . . ?
C5 P1 C10 105.37(8) . . ?
C5 P1 C14 108.12(9) . . ?
C10 P1 C14 113.87(10) . . ?
C1 N1 C9 125.29(18) . . ?
C8 N1 C1 108.53(15) . . ?
C8 N1 C9 126.10(18) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
N1 C1 C6 107.65(15) . . ?
N1 C1 C2 129.43(17) . . ?
C2 C1 C6 122.90(17) . . ?
C5 C4 H4 118.6 . . ?
C5 C4 C3 122.87(18) . . ?
C3 C4 H4 118.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
C1 C6 C7 106.50(15) . . ?
C5 C6 C1 118.80(15) . . ?
C5 C6 C7 134.68(15) . . ?
C4 C5 P1 123.83(14) . . ?
C4 C5 C6 116.98(15) . . ?
C6 C5 P1 119.19(12) . . ?
C6 C7 H7 126.5 . . ?
C8 C7 C6 106.94(16) . . ?
C8 C7 H7 126.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.98(17) . . ?
C2 C3 H3 119.5 . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.48(17) . . ?
C3 C2 H2 121.3 . . ?
N1 C8 H8 124.8 . . ?
C7 C8 N1 110.38(16) . . ?
C7 C8 H8 124.8 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
C13 C10 P1 104.07(15) . . ?
C11 C10 P1 109.14(17) . . ?
C11 C10 C13 107.1(2) . . ?
C12 C10 P1 115.66(15) . . ?
C12 C10 C13 109.5(2) . . ?
C12 C10 C11 110.8(2) . . ?
C16 C14 P1 116.53(16) . . ?
C16 C14 C17 108.9(2) . . ?
C17 C14 P1 106.71(16) . . ?
C15 C14 P1 107.45(17) . . ?
C15 C14 C16 108.3(2) . . ?
C15 C14 C17 108.7(2) . . ?
O2 P2 C22 111.59(8) . . ?
O2 P2 C31 108.90(9) . . ?
O2 P2 C27 108.81(9) . . ?
C22 P2 C31 105.85(9) . . ?
C22 P2 C27 108.23(9) . . ?
C31 P2 C27 113.48(10) . . ?
C25 N2 C26 125.2(2) . . ?
C25 N2 C18 108.40(16) . . ?
C18 N2 C26 126.3(2) . . ?
C22 C21 H21 119.0 . . ?
C22 C21 C20 121.9(2) . . ?
C20 C21 H21 119.0 . . ?
C21 C22 P2 122.32(16) . . ?
C21 C22 C23 117.73(17) . . ?
C23 C22 P2 119.95(13) . . ?
C33 C31 P2 115.32(16) . . ?
C33 C31 C32 109.9(2) . . ?
C33 C31 C34 108.5(2) . . ?
C32 C31 P2 110.17(15) . . ?
C34 C31 P2 104.75(16) . . ?
C34 C31 C32 107.90(19) . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
C22 C23 C18 118.66(17) . . ?
C22 C23 C24 135.26(16) . . ?
C18 C23 C24 106.08(17) . . ?
C20 C19 H19 121.4 . . ?
C20 C19 C18 117.28(18) . . ?
C18 C19 H19 121.4 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
N2 C25 H25 124.7 . . ?
C24 C25 N2 110.66(19) . . ?
C24 C25 H25 124.7 . . ?
C21 C20 H20 119.2 . . ?
C19 C20 C21 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29 C27 P2 106.27(14) . . ?
C28 C27 P2 107.34(15) . . ?
C28 C27 C29 107.9(2) . . ?
C28 C27 C30 109.8(2) . . ?
C30 C27 P2 116.79(16) . . ?
C30 C27 C29 108.40(19) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C18 C23 107.81(17) . . ?
N2 C18 C19 129.37(18) . . ?
C19 C18 C23 122.82(19) . . ?
C23 C24 H24 126.5 . . ?
C25 C24 C23 107.03(17) . . ?
C25 C24 H24 126.5 . . ?

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
O1 P1 C5 C4 165.44(16) . . . . ?
O1 P1 C5 C6 -13.86(17) . . . . ?
O1 P1 C10 C13 50.86(18) . . . . ?
O1 P1 C10 C11 -63.24(19) . . . . ?
O1 P1 C10 C12 171.0(2) . . . . ?
O1 P1 C14 C16 162.33(17) . . . . ?
O1 P1 C14 C17 -75.7(2) . . . . ?
O1 P1 C14 C15 40.6(2) . . . . ?
N1 C1 C6 C5 178.48(14) . . . . ?
N1 C1 C6 C7 -0.17(18) . . . . ?
N1 C1 C2 C3 -177.84(19) . . . . ?
C1 N1 C8 C7 -0.3(2) . . . . ?
C1 C6 C5 P1 179.09(12) . . . . ?
C1 C6 C5 C4 -0.3(2) . . . . ?
C1 C6 C7 C8 -0.04(19) . . . . ?
C4 C3 C2 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C7 C8 N1 0.2(2) . . . . ?
C5 P1 C10 C13 -68.62(18) . . . . ?
C5 P1 C10 C11 177.29(17) . . . . ?
C5 P1 C10 C12 51.5(2) . . . . ?
C5 P1 C14 C16 -77.27(18) . . . . ?
C5 P1 C14 C17 44.7(2) . . . . ?
C5 P1 C14 C15 161.05(17) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C5 C6 C7 C8 -178.37(19) . . . . ?
C7 C6 C5 P1 -2.7(3) . . . . ?
C7 C6 C5 C4 177.92(19) . . . . ?
C9 N1 C1 C6 177.11(17) . . . . ?
C9 N1 C1 C2 -4.6(3) . . . . ?
C9 N1 C8 C7 -177.12(18) . . . . ?
C3 C4 C5 P1 -179.08(16) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -178.63(16) . . . . ?
C8 N1 C1 C6 0.31(19) . . . . ?
C8 N1 C1 C2 178.64(18) . . . . ?
C10 P1 C5 C4 -75.72(18) . . . . ?
C10 P1 C5 C6 104.99(14) . . . . ?
C10 P1 C14 C16 39.5(2) . . . . ?
C10 P1 C14 C17 161.38(19) . . . . ?
C10 P1 C14 C15 -82.2(2) . . . . ?
C14 P1 C5 C4 46.39(19) . . . . ?
C14 P1 C5 C6 -132.90(14) . . . . ?
C14 P1 C10 C13 173.07(17) . . . . ?
C14 P1 C10 C11 59.0(2) . . . . ?
C14 P1 C10 C12 -66.8(2) . . . . ?
P2 C22 C23 C18 -179.40(14) . . . . ?
P2 C22 C23 C24 0.2(3) . . . . ?
O2 P2 C22 C21 165.62(18) . . . . ?
O2 P2 C22 C23 -14.48(19) . . . . ?
O2 P2 C31 C33 168.40(18) . . . . ?
O2 P2 C31 C32 -66.56(17) . . . . ?
O2 P2 C31 C34 49.25(16) . . . . ?
O2 P2 C27 C29 36.89(18) . . . . ?
O2 P2 C27 C28 -78.32(17) . . . . ?
O2 P2 C27 C30 157.94(16) . . . . ?
N2 C25 C24 C23 0.5(2) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C21 C22 C23 C24 -179.9(2) . . . . ?
C22 P2 C31 C33 48.3(2) . . . . ?
C22 P2 C31 C32 173.34(15) . . . . ?
C22 P2 C31 C34 -70.85(16) . . . . ?
C22 P2 C27 C29 158.33(15) . . . . ?
C22 P2 C27 C28 43.12(18) . . . . ?
C22 P2 C27 C30 -80.63(19) . . . . ?
C22 C21 C20 C19 -0.3(4) . . . . ?
C22 C23 C18 N2 178.88(17) . . . . ?
C22 C23 C18 C19 -0.6(3) . . . . ?
C22 C23 C24 C25 -179.4(2) . . . . ?
C31 P2 C22 C21 -76.0(2) . . . . ?
C31 P2 C22 C23 103.84(17) . . . . ?
C31 P2 C27 C29 -84.51(17) . . . . ?
C31 P2 C27 C28 160.28(16) . . . . ?
C31 P2 C27 C30 36.5(2) . . . . ?
C26 N2 C25 C24 -177.3(2) . . . . ?
C26 N2 C18 C23 177.4(2) . . . . ?
C26 N2 C18 C19 -3.2(4) . . . . ?
C25 N2 C18 C23 1.2(2) . . . . ?
C25 N2 C18 C19 -179.5(2) . . . . ?
C20 C21 C22 P2 179.79(19) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C20 C19 C18 N2 -179.1(2) . . . . ?
C20 C19 C18 C23 0.2(3) . . . . ?
C27 P2 C22 C21 45.9(2) . . . . ?
C27 P2 C22 C23 -134.19(16) . . . . ?
C27 P2 C31 C33 -70.2(2) . . . . ?
C27 P2 C31 C32 54.80(18) . . . . ?
C27 P2 C31 C34 170.61(14) . . . . ?
C18 N2 C25 C24 -1.0(2) . . . . ?
C18 C23 C24 C25 0.2(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C24 C23 C18 N2 -0.9(2) . . . . ?
C24 C23 C18 C19 179.71(19) . . . . ?

_olex2_date_sample_data_collection 2020-09-01
_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 1.977
_oxdiff_exptl_absorpt_empirical_full_min 0.484
