# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_191129huanghy_0m
_audit_block_doi                 10.5517/ccdc.csd.cc25ls8v
_database_code_depnum_ccdc_archive 'CCDC 2014047'
loop_
_audit_author_name
_audit_author_address
'haiyang huang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 N O3 P, C H Cl2'
_chemical_formula_sum            'C33 H23 Cl2 N O3 P'
_chemical_formula_weight         583.39
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.8411(17)
_cell_length_b                   12.359(2)
_cell_length_c                   14.778(3)
_cell_angle_alpha                97.562(4)
_cell_angle_beta                 107.094(3)
_cell_angle_gamma                107.232(3)
_cell_volume                     1431.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2081
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.069
_cell_measurement_theta_min      2.481
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0428 before and 0.0304 after correction.
The Ratio of minimum to maximum transmission is 0.9270.
The λ/2 correction factor is 0.00150.
;
_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    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             602
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8694
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_min         2.481
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3991
_reflns_number_total             6224
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6224
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0970P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.2039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl1-C9BA \\sim C9BA-Cl2A
 with sigma of 0.01
 Cl1A-C9BA \\sim C9BA-Cl2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(C9BA) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl1(0.55) Cl2(0.45) H9BB(0.5) H9BA(0.5) Cl1A(0.45) Cl2A(0.55)
5.a Secondary CH2 refined with riding coordinates:
 C9BA(H9BB,H9BA)
5.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20), C16(H16), C19(H19), C18(H18), C11(H11), C8(H8), C10(H10),
 C9(H9), C21(H21), C28(H28), C31(H31), C29(H29), C24(H24), C30(H30), C22(H22),
 C23(H23), C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
;
_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 0.15446(9) 0.19792(6) 0.01339(5) 0.0381(2) Uani 1 1 d . . . . .
O2 O 0.1076(3) 0.33089(17) 0.19212(15) 0.0502(5) Uani 1 1 d . . . . .
C13 C 0.0939(3) 0.2169(2) 0.18554(19) 0.0369(6) Uani 1 1 d . . . . .
C12 C 0.1576(3) 0.3948(2) 0.1294(2) 0.0405(6) Uani 1 1 d . . . . .
C14 C 0.1172(3) 0.1522(2) 0.1147(2) 0.0396(6) Uani 1 1 d . . . . .
H14 H 0.1134 0.0772 0.1195 0.048 Uiso 1 1 calc R . . . .
C7 C 0.1902(3) 0.3498(2) 0.0489(2) 0.0403(6) Uani 1 1 d . . . . .
C20 C 0.0149(4) 0.0605(3) 0.2727(2) 0.0502(7) Uani 1 1 d . . . . .
H20 H 0.0254 0.0083 0.2256 0.060 Uiso 1 1 calc R . . . .
C16 C 0.0325(3) 0.2531(3) 0.33953(19) 0.0424(7) Uani 1 1 d . . . . .
H16 H 0.0541 0.3309 0.3374 0.051 Uiso 1 1 calc R . . . .
C17 C -0.0130(4) 0.2145(3) 0.4142(2) 0.0483(8) Uani 1 1 d . . . . .
C15 C 0.0464(3) 0.1762(2) 0.26714(19) 0.0389(6) Uani 1 1 d . . . . .
C19 C -0.0316(5) 0.0228(3) 0.3471(3) 0.0650(10) Uani 1 1 d . . . . .
H19 H -0.0538 -0.0550 0.3496 0.078 Uiso 1 1 calc R . . . .
C18 C -0.0458(5) 0.0998(3) 0.4186(2) 0.0598(9) Uani 1 1 d . . . . .
H18 H -0.0770 0.0741 0.4691 0.072 Uiso 1 1 calc R . . . .
C11 C 0.1707(4) 0.5110(3) 0.1519(2) 0.0539(8) Uani 1 1 d . . . . .
H11 H 0.1454 0.5395 0.2049 0.065 Uiso 1 1 calc R . . . .
C8 C 0.2431(4) 0.4263(3) -0.0067(2) 0.0557(8) Uani 1 1 d . . . . .
H8 H 0.2674 0.3988 -0.0604 0.067 Uiso 1 1 calc R . . . .
C10 C 0.2210(5) 0.5824(3) 0.0954(3) 0.0630(9) Uani 1 1 d . . . . .
H10 H 0.2297 0.6600 0.1098 0.076 Uiso 1 1 calc R . . . .
C9 C 0.2594(5) 0.5404(3) 0.0166(3) 0.0674(10) Uani 1 1 d . . . . .
H9 H 0.2965 0.5904 -0.0205 0.081 Uiso 1 1 calc R . . . .
O1 O 0.0165(3) 0.13706(18) -0.08176(14) 0.0506(5) Uani 1 1 d . . . . .
N1 N -0.0306(3) 0.2954(3) 0.48619(17) 0.0583(8) Uani 1 1 d . . . . .
C1 C 0.3501(4) 0.1827(2) 0.0124(2) 0.0430(7) Uani 1 1 d . . . . .
O3 O -0.0640(4) 0.4590(2) 0.6209(2) 0.0821(8) Uani 1 1 d . . . . .
C25 C -0.2014(5) 0.3908(3) 0.5387(3) 0.0576(8) Uani 1 1 d . . . . .
C21 C -0.3281(4) 0.2474(4) 0.3888(2) 0.0689(11) Uani 1 1 d . . . . .
H21 H -0.3216 0.1932 0.3415 0.083 Uiso 1 1 calc R . . . .
C26 C -0.1868(4) 0.3102(3) 0.4699(2) 0.0479(7) Uani 1 1 d . . . . .
C27 C 0.0984(4) 0.3484(3) 0.5765(2) 0.0498(8) Uani 1 1 d . . . . .
C32 C 0.0786(4) 0.4298(3) 0.6425(2) 0.0581(9) Uani 1 1 d . . . . .
C28 C 0.2446(4) 0.3227(4) 0.6044(3) 0.0735(11) Uani 1 1 d . . . . .
H28 H 0.2592 0.2671 0.5621 0.088 Uiso 1 1 calc R . . . .
C31 C 0.2041(5) 0.4854(4) 0.7319(3) 0.0828(13) Uani 1 1 d . . . . .
H31 H 0.1903 0.5407 0.7748 0.099 Uiso 1 1 calc R . . . .
C29 C 0.3698(5) 0.3789(5) 0.6946(3) 0.0960(16) Uani 1 1 d . . . . .
H29 H 0.4683 0.3614 0.7122 0.115 Uiso 1 1 calc R . . . .
C24 C -0.3508(6) 0.4069(4) 0.5286(4) 0.0852(13) Uani 1 1 d . . . . .
H24 H -0.3581 0.4601 0.5764 0.102 Uiso 1 1 calc R . . . .
C30 C 0.3496(5) 0.4596(5) 0.7580(3) 0.0981(16) Uani 1 1 d . . . . .
H30 H 0.4339 0.4971 0.8185 0.118 Uiso 1 1 calc R . . . .
C22 C -0.4803(5) 0.2647(5) 0.3773(3) 0.0874(14) Uani 1 1 d . . . . .
H22 H -0.5751 0.2224 0.3223 0.105 Uiso 1 1 calc R . . . .
C23 C -0.4906(6) 0.3442(5) 0.4473(4) 0.0988(16) Uani 1 1 d . . . . .
H23 H -0.5925 0.3556 0.4397 0.119 Uiso 1 1 calc R . . . .
C6 C 0.3682(5) 0.1459(3) -0.0745(3) 0.0656(10) Uani 1 1 d . . . . .
H6 H 0.2801 0.1313 -0.1329 0.079 Uiso 1 1 calc R . . . .
C2 C 0.4856(4) 0.2046(4) 0.0978(3) 0.0671(10) Uani 1 1 d . . . . .
H2 H 0.4774 0.2303 0.1576 0.081 Uiso 1 1 calc R . . . .
C5 C 0.5170(6) 0.1306(4) -0.0757(4) 0.0872(14) Uani 1 1 d . . . . .
H5 H 0.5273 0.1056 -0.1350 0.105 Uiso 1 1 calc R . . . .
C3 C 0.6328(5) 0.1887(4) 0.0949(4) 0.0846(13) Uani 1 1 d . . . . .
H3 H 0.7225 0.2038 0.1526 0.101 Uiso 1 1 calc R . . . .
C4 C 0.6473(6) 0.1514(4) 0.0084(5) 0.0860(14) Uani 1 1 d . . . . .
H4 H 0.7460 0.1401 0.0068 0.103 Uiso 1 1 calc R . . . .
Cl1 Cl -0.2417(10) 0.1440(8) 0.7193(4) 0.251(3) Uani 0.55 1 d D U P A 1
Cl2 Cl -0.5010(12) 0.1036(11) 0.6694(6) 0.214(4) Uani 0.45 1 d D U P A 1
C9BA C -0.3643(8) 0.0966(13) 0.5998(9) 0.285(6) Uani 1 1 d D U . . .
H9BB H -0.3768 0.0192 0.5675 0.342 Uiso 0.5 1 calc R . P A 1
H9BA H -0.3500 0.1529 0.5603 0.342 Uiso 0.5 1 calc R . P A 1
Cl1A Cl -0.1591(9) 0.1992(4) 0.6921(4) 0.155(2) Uani 0.45 1 d D . P A 2
Cl2A Cl -0.5631(10) 0.0881(9) 0.5987(9) 0.288(5) Uani 0.55 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C14 1.753(3) . ?
P1 C7 1.787(3) . ?
P1 O1 1.483(2) . ?
P1 C1 1.798(3) . ?
O2 C13 1.366(3) . ?
O2 C12 1.381(3) . ?
C13 C14 1.334(4) . ?
C13 C15 1.489(4) . ?
C12 C7 1.388(4) . ?
C12 C11 1.393(4) . ?
C7 C8 1.399(4) . ?
C20 C15 1.392(4) . ?
C20 C19 1.372(4) . ?
C16 C17 1.375(4) . ?
C16 C15 1.393(4) . ?
C17 C18 1.375(5) . ?
C17 N1 1.437(4) . ?
C19 C18 1.387(5) . ?
C11 C10 1.361(5) . ?
C8 C9 1.360(5) . ?
C10 C9 1.384(5) . ?
N1 C26 1.402(4) . ?
N1 C27 1.394(4) . ?
C1 C6 1.376(4) . ?
C1 C2 1.389(5) . ?
O3 C25 1.385(4) . ?
O3 C32 1.373(4) . ?
C25 C26 1.390(4) . ?
C25 C24 1.361(5) . ?
C21 C26 1.379(4) . ?
C21 C22 1.389(5) . ?
C27 C32 1.393(4) . ?
C27 C28 1.381(5) . ?
C32 C31 1.377(5) . ?
C28 C29 1.385(5) . ?
C31 C30 1.374(6) . ?
C29 C30 1.365(6) . ?
C24 C23 1.373(6) . ?
C22 C23 1.373(6) . ?
C6 C5 1.388(5) . ?
C2 C3 1.385(5) . ?
C5 C4 1.355(7) . ?
C3 C4 1.356(7) . ?
Cl1 C9BA 1.692(11) . ?
Cl2 C9BA 1.816(12) . ?
C9BA Cl1A 1.868(11) . ?
C9BA Cl2A 1.724(11) . ?

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
C14 P1 C7 100.32(13) . . ?
C14 P1 C1 107.36(14) . . ?
C7 P1 C1 108.26(13) . . ?
O1 P1 C14 115.32(13) . . ?
O1 P1 C7 113.79(13) . . ?
O1 P1 C1 111.04(13) . . ?
C13 O2 C12 123.7(2) . . ?
O2 C13 C15 110.0(2) . . ?
C14 C13 O2 124.2(3) . . ?
C14 C13 C15 125.7(3) . . ?
O2 C12 C7 124.5(3) . . ?
O2 C12 C11 114.3(3) . . ?
C7 C12 C11 121.2(3) . . ?
C13 C14 P1 124.9(2) . . ?
C12 C7 P1 121.3(2) . . ?
C12 C7 C8 117.7(3) . . ?
C8 C7 P1 120.9(2) . . ?
C19 C20 C15 120.5(3) . . ?
C17 C16 C15 120.3(3) . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 N1 118.9(3) . . ?
C18 C17 N1 120.3(3) . . ?
C20 C15 C13 120.7(2) . . ?
C20 C15 C16 118.6(3) . . ?
C16 C15 C13 120.7(3) . . ?
C20 C19 C18 120.4(3) . . ?
C17 C18 C19 119.3(3) . . ?
C10 C11 C12 119.2(3) . . ?
C9 C8 C7 121.0(3) . . ?
C11 C10 C9 120.6(3) . . ?
C8 C9 C10 120.2(3) . . ?
C26 N1 C17 119.3(2) . . ?
C27 N1 C17 120.9(2) . . ?
C27 N1 C26 119.4(2) . . ?
C6 C1 P1 120.2(3) . . ?
C6 C1 C2 117.7(3) . . ?
C2 C1 P1 122.1(2) . . ?
C32 O3 C25 117.8(3) . . ?
O3 C25 C26 121.4(3) . . ?
C24 C25 O3 116.8(3) . . ?
C24 C25 C26 121.8(4) . . ?
C26 C21 C22 120.4(4) . . ?
C25 C26 N1 118.9(3) . . ?
C21 C26 N1 123.0(3) . . ?
C21 C26 C25 118.1(3) . . ?
C32 C27 N1 118.8(3) . . ?
C28 C27 N1 122.9(3) . . ?
C28 C27 C32 118.2(3) . . ?
O3 C32 C27 121.8(3) . . ?
O3 C32 C31 117.5(3) . . ?
C31 C32 C27 120.6(4) . . ?
C27 C28 C29 120.6(4) . . ?
C30 C31 C32 120.3(4) . . ?
C30 C29 C28 120.5(4) . . ?
C25 C24 C23 119.6(4) . . ?
C29 C30 C31 119.7(4) . . ?
C23 C22 C21 119.9(4) . . ?
C22 C23 C24 120.2(4) . . ?
C1 C6 C5 120.5(4) . . ?
C3 C2 C1 120.8(4) . . ?
C4 C5 C6 120.9(4) . . ?
C4 C3 C2 120.5(4) . . ?
C5 C4 C3 119.6(4) . . ?
Cl1 C9BA Cl2 72.2(7) . . ?
Cl2A C9BA Cl1A 126.0(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_200104huanghy_0m
_audit_block_doi                 10.5517/ccdc.csd.cc25lsbx
_database_code_depnum_ccdc_archive 'CCDC 2014049'
loop_
_audit_author_name
_audit_author_address
'haiyang huang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 N O2 P S'
_chemical_formula_sum            'C32 H22 N O2 P S'
_chemical_formula_weight         515.53
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   21.166(4)
_cell_length_b                   16.659(3)
_cell_length_c                   14.675(3)
_cell_angle_alpha                90
_cell_angle_beta                 89.963(4)
_cell_angle_gamma                90
_cell_volume                     5174.7(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4282
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.579
_cell_measurement_theta_min      2.668
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1277 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.8169.
The λ/2 correction factor is 0.00150.
;
_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    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30673
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         0.962
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5819
_reflns_number_total             11725
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         11725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      0.998
_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)+(0.0630P)²+1.1890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C7(H7), C16(H16), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C3(H3), C17(H17), C012(H012), C5(H5), C014(H014), C18(H18), C19(H19),
 C018(H018), C2(H2), C14(H14), C4(H4), C01D(H01D), C01E(H01E), C01F(H01F),
 C01G(H01G), C01H(H01H), C10(H10), C23(H23), C32(H32), C01L(H01L), C13(H13),
 C29(H29), C01O(H01O), C31(H31), C12(H12), C01R(H01R), C01S(H01S), C30(H30),
 C01U(H01U), C26(H26), C01W(H01W), C01X(H01X), C01Y(H01Y), C24(H24), C11(H11),
 C021(H021), C25(H25)
;
_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
P001 P 0.48480(4) 0.35687(5) 0.73596(6) 0.0396(2) Uani 1 1 d . . . . .
P1 P 0.98483(4) 0.35686(5) 0.76408(5) 0.0395(2) Uani 1 1 d . . . . .
S1 S 0.79653(6) 0.23950(6) 0.53365(7) 0.0805(4) Uani 1 1 d . . . . .
S004 S 0.29652(6) 0.23948(6) 0.96633(7) 0.0809(4) Uani 1 1 d . . . . .
O005 O 0.45734(10) 0.18015(12) 0.80162(14) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.95727(10) 0.18011(12) 0.69783(14) 0.0486(6) Uani 1 1 d . . . . .
O007 O 0.53765(10) 0.39104(13) 0.68252(14) 0.0522(6) Uani 1 1 d . . . . .
O1 O 1.03767(10) 0.39102(13) 0.81755(15) 0.0534(6) Uani 1 1 d . . . . .
N1 N 0.82332(11) 0.14066(15) 0.70307(16) 0.0394(6) Uani 1 1 d . . . . .
N00A N 0.32327(11) 0.14073(15) 0.79699(16) 0.0404(6) Uani 1 1 d . . . . .
C00B C 0.43434(13) 0.20589(17) 0.7192(2) 0.0360(7) Uani 1 1 d . . . . .
C8 C 0.93439(13) 0.20557(17) 0.78056(19) 0.0365(7) Uani 1 1 d . . . . .
C15 C 0.90032(13) 0.13936(17) 0.82649(19) 0.0352(7) Uani 1 1 d . . . . .
C00E C 0.40022(13) 0.13926(17) 0.67365(19) 0.0347(7) Uani 1 1 d . . . . .
C6 C 1.00856(13) 0.30805(18) 0.66123(19) 0.0372(7) Uani 1 1 d . . . . .
C22 C 0.77567(14) 0.20049(18) 0.7129(2) 0.0412(7) Uani 1 1 d . . . . .
C00H C 0.34688(13) 0.10565(17) 0.71383(19) 0.0369(7) Uani 1 1 d . . . . .
C21 C 0.84691(13) 0.10566(17) 0.78602(19) 0.0371(7) Uani 1 1 d . . . . .
C00J C 0.50860(13) 0.30815(18) 0.8387(2) 0.0388(7) Uani 1 1 d . . . . .
C00K C 0.44192(14) 0.27827(17) 0.6845(2) 0.0403(7) Uani 1 1 d . . . . .
H00K H 0.4232 0.2887 0.6285 0.048 Uiso 1 1 calc R . . . .
C33 C 0.83375(14) 0.10019(18) 0.6196(2) 0.0401(7) Uani 1 1 d . . . . .
C00M C 0.33353(14) 0.10045(18) 0.8804(2) 0.0389(7) Uani 1 1 d . . . . .
C00N C 0.27568(14) 0.20043(18) 0.7872(2) 0.0419(7) Uani 1 1 d . . . . .
C00O C 0.49305(13) 0.22890(19) 0.8582(2) 0.0405(7) Uani 1 1 d . . . . .
C00P C 0.42920(14) 0.43395(18) 0.7681(2) 0.0414(7) Uani 1 1 d . . . . .
C1 C 0.99319(14) 0.22866(19) 0.6417(2) 0.0408(7) Uani 1 1 d . . . . .
C7 C 0.94182(14) 0.27826(18) 0.8154(2) 0.0413(7) Uani 1 1 d . . . . .
H7 H 0.9229 0.2887 0.8714 0.050 Uiso 1 1 calc R . . . .
C9 C 0.92930(14) 0.43371(18) 0.7322(2) 0.0413(7) Uani 1 1 d . . . . .
C16 C 0.92036(15) 0.11046(19) 0.9100(2) 0.0468(8) Uani 1 1 d . . . . .
H16 H 0.9558 0.1328 0.9376 0.056 Uiso 1 1 calc R . . . .
C00U C 0.42010(15) 0.11033(19) 0.5898(2) 0.0464(8) Uani 1 1 d . . . . .
H00U H 0.4554 0.1329 0.5620 0.056 Uiso 1 1 calc R . . . .
C00V C 0.38847(16) 0.04883(19) 0.5471(2) 0.0503(8) Uani 1 1 d . . . . .
H00V H 0.4025 0.0299 0.4910 0.060 Uiso 1 1 calc R . . . .
C00W C 0.55111(15) 0.2333(2) 0.9979(2) 0.0538(9) Uani 1 1 d . . . . .
H00W H 0.5651 0.2085 1.0509 0.065 Uiso 1 1 calc R . . . .
C00X C 0.31762(15) 0.1365(2) 0.9638(2) 0.0490(8) Uani 1 1 d . . . . .
C00Y C 0.33618(16) 0.0154(2) 0.5871(2) 0.0531(9) Uani 1 1 d . . . . .
H00Y H 0.3148 -0.0261 0.5581 0.064 Uiso 1 1 calc R . . . .
C28 C 0.81767(15) 0.1364(2) 0.5365(2) 0.0491(8) Uani 1 1 d . . . . .
C3 C 1.05109(15) 0.2330(2) 0.5020(2) 0.0537(9) Uani 1 1 d . . . . .
H3 H 1.0651 0.2083 0.4489 0.064 Uiso 1 1 calc R . . . .
C17 C 0.88828(16) 0.04875(19) 0.9529(2) 0.0508(8) Uani 1 1 d . . . . .
H17 H 0.9022 0.0298 1.0090 0.061 Uiso 1 1 calc R . . . .
C012 C 0.31528(15) 0.04326(19) 0.6705(2) 0.0488(8) Uani 1 1 d . . . . .
H012 H 0.2800 0.0202 0.6977 0.059 Uiso 1 1 calc R . . . .
C5 C 1.04687(15) 0.3481(2) 0.5985(2) 0.0503(8) Uani 1 1 d . . . . .
H5 H 1.0583 0.4010 0.6101 0.060 Uiso 1 1 calc R . . . .
C014 C 0.54695(15) 0.3480(2) 0.9016(2) 0.0501(8) Uani 1 1 d . . . . .
H014 H 0.5584 0.4009 0.8901 0.060 Uiso 1 1 calc R . . . .
C27 C 0.75622(15) 0.24586(18) 0.6376(2) 0.0476(8) Uani 1 1 d . . . . .
C18 C 0.83602(16) 0.0154(2) 0.9129(2) 0.0524(9) Uani 1 1 d . . . . .
H18 H 0.8145 -0.0261 0.9418 0.063 Uiso 1 1 calc R . . . .
C19 C 0.81526(15) 0.04345(19) 0.8295(2) 0.0482(8) Uani 1 1 d . . . . .
H19 H 0.7799 0.0206 0.8023 0.058 Uiso 1 1 calc R . . . .
C018 C 0.36915(16) 0.4153(2) 0.8000(2) 0.0515(9) Uani 1 1 d . . . . .
H018 H 0.3564 0.3620 0.8046 0.062 Uiso 1 1 calc R . . . .
C2 C 1.01348(16) 0.1915(2) 0.5618(2) 0.0529(9) Uani 1 1 d . . . . .
H2 H 1.0016 0.1389 0.5492 0.063 Uiso 1 1 calc R . . . .
C14 C 0.86928(15) 0.4150(2) 0.6999(2) 0.0510(8) Uani 1 1 d . . . . .
H14 H 0.8566 0.3617 0.6954 0.061 Uiso 1 1 calc R . . . .
C4 C 1.06830(15) 0.3116(2) 0.5202(2) 0.0555(9) Uani 1 1 d . . . . .
H4 H 1.0941 0.3396 0.4798 0.067 Uiso 1 1 calc R . . . .
C01C C 0.25630(16) 0.24600(18) 0.8624(2) 0.0488(8) Uani 1 1 d . . . . .
C01D C 0.24712(16) 0.2153(2) 0.7034(2) 0.0573(9) Uani 1 1 d . . . . .
H01D H 0.2598 0.1866 0.6523 0.069 Uiso 1 1 calc R . . . .
C01E C 0.51353(16) 0.1917(2) 0.9378(2) 0.0518(9) Uani 1 1 d . . . . .
H01E H 0.5018 0.1390 0.9503 0.062 Uiso 1 1 calc R . . . .
C01F C 0.56822(15) 0.3117(2) 0.9797(2) 0.0554(9) Uani 1 1 d . . . . .
H01F H 0.5939 0.3397 1.0201 0.066 Uiso 1 1 calc R . . . .
C01G C 0.44696(17) 0.51382(19) 0.7612(2) 0.0555(9) Uani 1 1 d . . . . .
H01G H 0.4867 0.5269 0.7387 0.067 Uiso 1 1 calc R . . . .
C01H C 0.36116(15) 0.02502(19) 0.8835(2) 0.0513(9) Uani 1 1 d . . . . .
H01H H 0.3733 0.0000 0.8296 0.062 Uiso 1 1 calc R . . . .
C10 C 0.94717(16) 0.51371(19) 0.7387(2) 0.0552(9) Uani 1 1 d . . . . .
H10 H 0.9871 0.5269 0.7604 0.066 Uiso 1 1 calc R . . . .
C23 C 0.74685(16) 0.2152(2) 0.7964(3) 0.0583(9) Uani 1 1 d . . . . .
H23 H 0.7592 0.1860 0.8474 0.070 Uiso 1 1 calc R . . . .
C32 C 0.86118(15) 0.0250(2) 0.6164(2) 0.0515(8) Uani 1 1 d . . . . .
H32 H 0.8731 -0.0003 0.6702 0.062 Uiso 1 1 calc R . . . .
C01L C 0.32509(18) 0.0965(2) 1.0448(2) 0.0631(10) Uani 1 1 d . . . . .
H01L H 0.3121 0.1204 1.0989 0.076 Uiso 1 1 calc R . . . .
C13 C 0.82834(18) 0.4763(3) 0.6744(2) 0.0633(10) Uani 1 1 d . . . . .
H13 H 0.7881 0.4639 0.6531 0.076 Uiso 1 1 calc R . . . .
C29 C 0.82517(18) 0.0966(2) 0.4553(2) 0.0643(10) Uani 1 1 d . . . . .
H29 H 0.8124 0.1207 0.4012 0.077 Uiso 1 1 calc R . . . .
C01O C 0.3469(2) 0.5547(3) 0.8194(3) 0.0717(12) Uani 1 1 d . . . . .
H01O H 0.3194 0.5953 0.8373 0.086 Uiso 1 1 calc R . . . .
C31 C 0.87100(18) -0.0131(2) 0.5340(3) 0.0645(10) Uani 1 1 d . . . . .
H31 H 0.8911 -0.0628 0.5332 0.077 Uiso 1 1 calc R . . . .
C12 C 0.8469(2) 0.5546(3) 0.6805(3) 0.0726(12) Uani 1 1 d . . . . .
H12 H 0.8194 0.5952 0.6627 0.087 Uiso 1 1 calc R . . . .
C01R C 0.32841(17) 0.4763(3) 0.8249(2) 0.0631(10) Uani 1 1 d . . . . .
H01R H 0.2881 0.4639 0.8457 0.076 Uiso 1 1 calc R . . . .
C01S C 0.37082(18) -0.0134(2) 0.9660(3) 0.0633(10) Uani 1 1 d . . . . .
H01S H 0.3905 -0.0633 0.9668 0.076 Uiso 1 1 calc R . . . .
C30 C 0.85176(19) 0.0205(2) 0.4537(3) 0.0698(11) Uani 1 1 d . . . . .
H30 H 0.8564 -0.0071 0.3990 0.084 Uiso 1 1 calc R . . . .
C01U C 0.20799(18) 0.3011(2) 0.8533(3) 0.0688(11) Uani 1 1 d . . . . .
H01U H 0.1942 0.3295 0.9041 0.083 Uiso 1 1 calc R . . . .
C26 C 0.70779(18) 0.3011(2) 0.6471(3) 0.0674(11) Uani 1 1 d . . . . .
H26 H 0.6939 0.3294 0.5964 0.081 Uiso 1 1 calc R . . . .
C01W C 0.35188(19) 0.0207(2) 1.0463(3) 0.0686(11) Uani 1 1 d . . . . .
H01W H 0.3569 -0.0066 1.1010 0.082 Uiso 1 1 calc R . . . .
C01X C 0.4061(2) 0.5738(2) 0.7873(3) 0.0701(11) Uani 1 1 d . . . . .
H01X H 0.4185 0.6273 0.7833 0.084 Uiso 1 1 calc R . . . .
C01Y C 0.20032(19) 0.2724(3) 0.6958(3) 0.0757(12) Uani 1 1 d . . . . .
H01Y H 0.1823 0.2824 0.6391 0.091 Uiso 1 1 calc R . . . .
C24 C 0.70020(18) 0.2723(2) 0.8046(3) 0.0741(12) Uani 1 1 d . . . . .
H24 H 0.6822 0.2823 0.8613 0.089 Uiso 1 1 calc R . . . .
C11 C 0.9059(2) 0.5738(2) 0.7128(3) 0.0720(11) Uani 1 1 d . . . . .
H11 H 0.9181 0.6273 0.7173 0.086 Uiso 1 1 calc R . . . .
C021 C 0.17986(19) 0.3146(2) 0.7699(3) 0.0797(13) Uani 1 1 d . . . . .
H021 H 0.1474 0.3519 0.7643 0.096 Uiso 1 1 calc R . . . .
C25 C 0.68000(19) 0.3146(2) 0.7302(3) 0.0787(13) Uani 1 1 d . . . . .
H25 H 0.6478 0.3522 0.7360 0.094 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 O007 1.480(2) . ?
P001 C00J 1.785(3) . ?
P001 C00K 1.763(3) . ?
P001 C00P 1.804(3) . ?
P1 O1 1.480(2) . ?
P1 C6 1.786(3) . ?
P1 C7 1.764(3) . ?
P1 C9 1.800(3) . ?
S1 C28 1.775(3) . ?
S1 C27 1.751(4) . ?
S004 C00X 1.773(3) . ?
S004 C01C 1.750(4) . ?
O005 C00B 1.373(3) . ?
O005 C00O 1.386(3) . ?
O2 C8 1.374(3) . ?
O2 C1 1.382(4) . ?
N1 C22 1.425(4) . ?
N1 C21 1.439(3) . ?
N1 C33 1.415(4) . ?
N00A C00H 1.442(4) . ?
N00A C00M 1.412(4) . ?
N00A C00N 1.423(4) . ?
C00B C00E 1.484(4) . ?
C00B C00K 1.319(4) . ?
C8 C15 1.480(4) . ?
C8 C7 1.324(4) . ?
C15 C21 1.395(4) . ?
C15 C16 1.384(4) . ?
C00E C00H 1.391(4) . ?
C00E C00U 1.387(4) . ?
C6 C1 1.392(4) . ?
C6 C5 1.395(4) . ?
C22 C27 1.401(4) . ?
C22 C23 1.390(4) . ?
C00H C012 1.390(4) . ?
C21 C19 1.389(4) . ?
C00J C00O 1.391(4) . ?
C00J C014 1.398(4) . ?
C00K H00K 0.9300 . ?
C33 C28 1.403(4) . ?
C33 C32 1.382(4) . ?
C00M C00X 1.404(4) . ?
C00M C01H 1.387(4) . ?
C00N C01C 1.400(4) . ?
C00N C01D 1.393(4) . ?
C00O C01E 1.392(4) . ?
C00P C018 1.389(4) . ?
C00P C01G 1.386(4) . ?
C1 C2 1.393(4) . ?
C7 H7 0.9300 . ?
C9 C14 1.392(4) . ?
C9 C10 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(4) . ?
C00U H00U 0.9300 . ?
C00U C00V 1.375(4) . ?
C00V H00V 0.9300 . ?
C00V C00Y 1.371(5) . ?
C00W H00W 0.9300 . ?
C00W C01E 1.374(4) . ?
C00W C01F 1.382(5) . ?
C00X C01L 1.372(4) . ?
C00Y H00Y 0.9300 . ?
C00Y C012 1.381(4) . ?
C28 C29 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.372(5) . ?
C3 C4 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.370(4) . ?
C012 H012 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.377(5) . ?
C014 H014 0.9300 . ?
C014 C01F 1.373(4) . ?
C27 C26 1.384(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9300 . ?
C018 H018 0.9300 . ?
C018 C01R 1.382(5) . ?
C2 H2 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.391(5) . ?
C4 H4 0.9300 . ?
C01C C01U 1.380(5) . ?
C01D H01D 0.9300 . ?
C01D C01Y 1.378(5) . ?
C01E H01E 0.9300 . ?
C01F H01F 0.9300 . ?
C01G H01G 0.9300 . ?
C01G C01X 1.377(5) . ?
C01H H01H 0.9300 . ?
C01H C01S 1.385(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(5) . ?
C32 H32 0.9300 . ?
C32 C31 1.381(5) . ?
C01L H01L 0.9300 . ?
C01L C01W 1.384(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.365(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.386(5) . ?
C01O H01O 0.9300 . ?
C01O C01R 1.366(5) . ?
C01O C01X 1.375(6) . ?
C31 H31 0.9300 . ?
C31 C30 1.368(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.375(6) . ?
C01R H01R 0.9300 . ?
C01S H01S 0.9300 . ?
C01S C01W 1.368(5) . ?
C30 H30 0.9300 . ?
C01U H01U 0.9300 . ?
C01U C021 1.379(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.372(5) . ?
C01W H01W 0.9300 . ?
C01X H01X 0.9300 . ?
C01Y H01Y 0.9300 . ?
C01Y C021 1.365(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.367(5) . ?
C11 H11 0.9300 . ?
C021 H021 0.9300 . ?
C25 H25 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
O007 P001 C00J 114.13(13) . . ?
O007 P001 C00K 116.61(14) . . ?
O007 P001 C00P 110.94(14) . . ?
C00J P001 C00P 106.71(14) . . ?
C00K P001 C00J 99.76(14) . . ?
C00K P001 C00P 107.73(14) . . ?
O1 P1 C6 114.25(14) . . ?
O1 P1 C7 116.67(14) . . ?
O1 P1 C9 110.97(14) . . ?
C6 P1 C9 106.71(14) . . ?
C7 P1 C6 99.67(15) . . ?
C7 P1 C9 107.59(14) . . ?
C27 S1 C28 99.23(15) . . ?
C01C S004 C00X 99.46(15) . . ?
C00B O005 C00O 122.6(2) . . ?
C8 O2 C1 122.6(2) . . ?
C22 N1 C21 116.3(2) . . ?
C33 N1 C22 122.1(2) . . ?
C33 N1 C21 119.0(2) . . ?
C00M N00A C00H 119.2(2) . . ?
C00M N00A C00N 121.9(2) . . ?
C00N N00A C00H 116.3(2) . . ?
O005 C00B C00E 109.7(2) . . ?
C00K C00B O005 125.6(3) . . ?
C00K C00B C00E 124.7(3) . . ?
O2 C8 C15 110.1(2) . . ?
C7 C8 O2 125.6(3) . . ?
C7 C8 C15 124.3(3) . . ?
C21 C15 C8 120.0(2) . . ?
C16 C15 C8 120.9(3) . . ?
C16 C15 C21 119.1(3) . . ?
C00H C00E C00B 120.4(3) . . ?
C00U C00E C00B 120.8(3) . . ?
C00U C00E C00H 118.8(3) . . ?
C1 C6 P1 122.7(2) . . ?
C1 C6 C5 117.0(3) . . ?
C5 C6 P1 120.2(2) . . ?
C27 C22 N1 120.4(3) . . ?
C23 C22 N1 121.5(3) . . ?
C23 C22 C27 118.1(3) . . ?
C00E C00H N00A 118.5(2) . . ?
C012 C00H N00A 121.6(3) . . ?
C012 C00H C00E 119.8(3) . . ?
C15 C21 N1 118.6(2) . . ?
C19 C21 N1 121.5(3) . . ?
C19 C21 C15 119.7(3) . . ?
C00O C00J P001 122.6(2) . . ?
C00O C00J C014 116.9(3) . . ?
C014 C00J P001 120.4(2) . . ?
P001 C00K H00K 117.4 . . ?
C00B C00K P001 125.2(2) . . ?
C00B C00K H00K 117.4 . . ?
C28 C33 N1 120.6(3) . . ?
C32 C33 N1 121.8(3) . . ?
C32 C33 C28 117.6(3) . . ?
C00X C00M N00A 121.0(3) . . ?
C01H C00M N00A 121.6(3) . . ?
C01H C00M C00X 117.4(3) . . ?
C01C C00N N00A 120.4(3) . . ?
C01D C00N N00A 121.4(3) . . ?
C01D C00N C01C 118.2(3) . . ?
O005 C00O C00J 124.2(3) . . ?
O005 C00O C01E 114.4(3) . . ?
C00J C00O C01E 121.5(3) . . ?
C018 C00P P001 121.7(2) . . ?
C01G C00P P001 119.1(3) . . ?
C01G C00P C018 119.1(3) . . ?
O2 C1 C6 124.2(3) . . ?
O2 C1 C2 114.2(3) . . ?
C6 C1 C2 121.6(3) . . ?
P1 C7 H7 117.4 . . ?
C8 C7 P1 125.1(2) . . ?
C8 C7 H7 117.4 . . ?
C14 C9 P1 121.7(2) . . ?
C10 C9 P1 119.2(2) . . ?
C10 C9 C14 119.1(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C00E C00U H00U 119.5 . . ?
C00V C00U C00E 121.1(3) . . ?
C00V C00U H00U 119.5 . . ?
C00U C00V H00V 120.0 . . ?
C00Y C00V C00U 120.0(3) . . ?
C00Y C00V H00V 120.0 . . ?
C01E C00W H00W 119.9 . . ?
C01E C00W C01F 120.3(3) . . ?
C01F C00W H00W 119.9 . . ?
C00M C00X S004 119.5(3) . . ?
C01L C00X S004 118.7(3) . . ?
C01L C00X C00M 121.4(3) . . ?
C00V C00Y H00Y 120.0 . . ?
C00V C00Y C012 120.1(3) . . ?
C012 C00Y H00Y 120.0 . . ?
C33 C28 S1 119.9(3) . . ?
C29 C28 S1 118.4(3) . . ?
C29 C28 C33 121.2(3) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C00H C012 H012 119.9 . . ?
C00Y C012 C00H 120.2(3) . . ?
C00Y C012 H012 119.9 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C00J C014 H014 118.9 . . ?
C01F C014 C00J 122.2(3) . . ?
C01F C014 H014 118.9 . . ?
C22 C27 S1 120.8(3) . . ?
C26 C27 S1 119.2(3) . . ?
C26 C27 C22 119.8(3) . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C21 C19 H19 119.8 . . ?
C18 C19 C21 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C00P C018 H018 120.2 . . ?
C01R C018 C00P 119.7(3) . . ?
C01R C018 H018 120.2 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C00N C01C S004 120.7(3) . . ?
C01U C01C S004 119.1(3) . . ?
C01U C01C C00N 120.0(3) . . ?
C00N C01D H01D 119.7 . . ?
C01Y C01D C00N 120.5(4) . . ?
C01Y C01D H01D 119.7 . . ?
C00O C01E H01E 120.2 . . ?
C00W C01E C00O 119.7(3) . . ?
C00W C01E H01E 120.2 . . ?
C00W C01F H01F 120.3 . . ?
C014 C01F C00W 119.4(3) . . ?
C014 C01F H01F 120.3 . . ?
C00P C01G H01G 119.8 . . ?
C01X C01G C00P 120.4(4) . . ?
C01X C01G H01G 119.8 . . ?
C00M C01H H01H 119.7 . . ?
C01S C01H C00M 120.6(3) . . ?
C01S C01H H01H 119.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C33 C32 H32 119.7 . . ?
C31 C32 C33 120.7(3) . . ?
C31 C32 H32 119.7 . . ?
C00X C01L H01L 119.9 . . ?
C00X C01L C01W 120.2(3) . . ?
C01W C01L H01L 119.9 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C01R C01O H01O 119.9 . . ?
C01R C01O C01X 120.2(4) . . ?
C01X C01O H01O 119.9 . . ?
C32 C31 H31 119.3 . . ?
C30 C31 C32 121.4(4) . . ?
C30 C31 H31 119.3 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.5(4) . . ?
C11 C12 H12 119.8 . . ?
C018 C01R H01R 119.7 . . ?
C01O C01R C018 120.6(4) . . ?
C01O C01R H01R 119.7 . . ?
C01H C01S H01S 119.4 . . ?
C01W C01S C01H 121.2(3) . . ?
C01W C01S H01S 119.4 . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.8(4) . . ?
C31 C30 H30 120.6 . . ?
C01C C01U H01U 119.5 . . ?
C021 C01U C01C 121.0(4) . . ?
C021 C01U H01U 119.5 . . ?
C27 C26 H26 119.5 . . ?
C25 C26 C27 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C01L C01W H01W 120.5 . . ?
C01S C01W C01L 119.0(3) . . ?
C01S C01W H01W 120.5 . . ?
C01G C01X H01X 120.0 . . ?
C01O C01X C01G 120.0(4) . . ?
C01O C01X H01X 120.0 . . ?
C01D C01Y H01Y 119.4 . . ?
C021 C01Y C01D 121.2(4) . . ?
C021 C01Y H01Y 119.4 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(4) . . ?
C25 C24 H24 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C01U C021 H021 120.5 . . ?
C01Y C021 C01U 119.1(4) . . ?
C01Y C021 H021 120.5 . . ?
C26 C25 H25 120.3 . . ?
C24 C25 C26 119.3(4) . . ?
C24 C25 H25 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_191223huanghy_0m
_audit_block_doi                 10.5517/ccdc.csd.cc25ls9w
_database_code_depnum_ccdc_archive 'CCDC 2014048'
loop_
_audit_author_name
_audit_author_address
'haiyang huang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2021-02-05 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H29 N2 O4 P'
_chemical_formula_sum            'C44 H29 N2 O4 P'
_chemical_formula_weight         680.66
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   27.765(7)
_cell_length_b                   11.840(3)
_cell_length_c                   25.681(7)
_cell_angle_alpha                90
_cell_angle_beta                 126.333(4)
_cell_angle_gamma                90
_cell_volume                     6801(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.871
_cell_measurement_theta_min      2.354
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0633 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9077.
The λ/2 correction factor is 0.00150.
;
_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    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20206
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.647
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3982
_reflns_number_total             7554
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         7554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      0.991
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C16(H16), C20(H20), C18(H18), C14(H14), C2(H2), C5(H5), C10(H10),
 C3(H3), C40(H40), C4(H4), C43(H43), C12(H12), C34(H34), C13(H13), C37(H37),
 C11(H11), C35(H35), C26(H26), C36(H36), C32(H32), C23(H23), C41(H41), C42(H42),
  C24(H24), C29(H29), C31(H31), C25(H25), C30(H30)
;
_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 0.53741(3) 0.32328(5) 0.55526(3) 0.03667(18) Uani 1 1 d . . . . .
O2 O 0.57753(7) 0.39432(13) 0.54877(8) 0.0446(4) Uani 1 1 d . . . . .
O1 O 0.49468(8) 0.30373(15) 0.64383(8) 0.0535(5) Uani 1 1 d . . . . .
O3 O 0.27509(9) 0.40729(16) 0.71992(9) 0.0624(5) Uani 1 1 d . . . . .
N1 N 0.33660(9) 0.42700(18) 0.66465(10) 0.0493(6) Uani 1 1 d . . . . .
N2 N 0.33423(10) 0.70827(18) 0.52448(11) 0.0511(6) Uani 1 1 d . . . . .
C6 C 0.54798(11) 0.2519(2) 0.66497(12) 0.0409(6) Uani 1 1 d . . . . .
C7 C 0.46635(10) 0.37889(19) 0.59316(11) 0.0379(6) Uani 1 1 d . . . . .
O4 O 0.31714(12) 0.9086(2) 0.45779(15) 0.0967(8) Uani 1 1 d . . . . .
C1 C 0.57302(10) 0.25462(19) 0.63148(11) 0.0364(6) Uani 1 1 d . . . . .
C15 C 0.41964(10) 0.44145(19) 0.59205(11) 0.0374(6) Uani 1 1 d . . . . .
C8 C 0.47977(10) 0.39310(19) 0.55148(11) 0.0386(6) Uani 1 1 d . . . . .
H8 H 0.4567 0.4440 0.5178 0.046 Uiso 1 1 calc R . . . .
C9 C 0.50287(11) 0.21598(19) 0.49397(11) 0.0389(6) Uani 1 1 d . . . . .
C44 C 0.28843(11) 0.3520(2) 0.63815(12) 0.0432(6) Uani 1 1 d . . . . .
C16 C 0.39692(10) 0.5415(2) 0.55748(11) 0.0393(6) Uani 1 1 d . . . . .
H16 H 0.4098 0.5673 0.5334 0.047 Uiso 1 1 calc R . . . .
C39 C 0.25878(12) 0.3430(2) 0.66697(12) 0.0465(7) Uani 1 1 d . . . . .
C17 C 0.35535(11) 0.6030(2) 0.55868(12) 0.0415(6) Uani 1 1 d . . . . .
C19 C 0.35679(11) 0.4648(2) 0.62724(12) 0.0433(6) Uani 1 1 d . . . . .
C20 C 0.39936(11) 0.4037(2) 0.62781(12) 0.0419(6) Uani 1 1 d . . . . .
H20 H 0.4146 0.3375 0.6519 0.050 Uiso 1 1 calc R . . . .
C18 C 0.33446(11) 0.5641(2) 0.59269(12) 0.0460(7) Uani 1 1 d . . . . .
H18 H 0.3055 0.6047 0.5923 0.055 Uiso 1 1 calc R . . . .
C14 C 0.52492(13) 0.1962(2) 0.45826(13) 0.0542(7) Uani 1 1 d . . . . .
H14 H 0.5577 0.2369 0.4673 0.065 Uiso 1 1 calc R . . . .
C38 C 0.32696(12) 0.4697(2) 0.75008(12) 0.0462(6) Uani 1 1 d . . . . .
C33 C 0.35792(11) 0.4827(2) 0.72289(12) 0.0437(6) Uani 1 1 d . . . . .
C2 C 0.62831(11) 0.2024(2) 0.66037(13) 0.0520(7) Uani 1 1 d . . . . .
H2 H 0.6465 0.2043 0.6395 0.062 Uiso 1 1 calc R . . . .
C27 C 0.35393(13) 0.8116(2) 0.55787(16) 0.0577(8) Uani 1 1 d . . . . .
C21 C 0.29889(12) 0.7087(3) 0.45673(14) 0.0543(7) Uani 1 1 d . . . . .
C5 C 0.57581(12) 0.1966(2) 0.72358(12) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.5580 0.1945 0.7448 0.065 Uiso 1 1 calc R . . . .
C10 C 0.45463(12) 0.1535(2) 0.48047(14) 0.0572(7) Uani 1 1 d . . . . .
H10 H 0.4398 0.1649 0.5044 0.069 Uiso 1 1 calc R . . . .
C3 C 0.65659(12) 0.1482(2) 0.71877(14) 0.0584(8) Uani 1 1 d . . . . .
H3 H 0.6935 0.1138 0.7371 0.070 Uiso 1 1 calc R . . . .
C40 C 0.21225(13) 0.2691(3) 0.64337(15) 0.0637(8) Uani 1 1 d . . . . .
H40 H 0.1934 0.2637 0.6635 0.076 Uiso 1 1 calc R . . . .
C4 C 0.62981(13) 0.1452(2) 0.75011(13) 0.0577(8) Uani 1 1 d . . . . .
H4 H 0.6486 0.1079 0.7895 0.069 Uiso 1 1 calc R . . . .
C43 C 0.26900(13) 0.2849(2) 0.58545(13) 0.0598(8) Uani 1 1 d . . . . .
H43 H 0.2880 0.2893 0.5654 0.072 Uiso 1 1 calc R . . . .
C22 C 0.29115(14) 0.8094(3) 0.42465(17) 0.0681(9) Uani 1 1 d . . . . .
C12 C 0.45051(15) 0.0574(3) 0.39631(15) 0.0736(9) Uani 1 1 d . . . . .
H12 H 0.4324 0.0047 0.3630 0.088 Uiso 1 1 calc R . . . .
C34 C 0.40811(12) 0.5493(2) 0.75485(13) 0.0571(7) Uani 1 1 d . . . . .
H34 H 0.4297 0.5580 0.7380 0.069 Uiso 1 1 calc R . . . .
C13 C 0.49875(15) 0.1172(3) 0.40986(15) 0.0715(9) Uani 1 1 d . . . . .
H13 H 0.5138 0.1043 0.3863 0.086 Uiso 1 1 calc R . . . .
C37 C 0.34674(14) 0.5214(3) 0.80735(13) 0.0615(8) Uani 1 1 d . . . . .
H37 H 0.3263 0.5105 0.8254 0.074 Uiso 1 1 calc R . . . .
C11 C 0.42840(13) 0.0742(3) 0.43145(16) 0.0708(9) Uani 1 1 d . . . . .
H11 H 0.3959 0.0323 0.4223 0.085 Uiso 1 1 calc R . . . .
C35 C 0.42725(13) 0.6037(3) 0.81184(14) 0.0679(9) Uani 1 1 d . . . . .
H35 H 0.4608 0.6501 0.8323 0.082 Uiso 1 1 calc R . . . .
C28 C 0.34325(16) 0.9102(3) 0.5233(2) 0.0773(10) Uani 1 1 d . . . . .
C26 C 0.27082(14) 0.6139(3) 0.42026(16) 0.0754(9) Uani 1 1 d . . . . .
H26 H 0.2748 0.5457 0.4405 0.090 Uiso 1 1 calc R . . . .
C36 C 0.39661(15) 0.5892(3) 0.83822(15) 0.0702(9) Uani 1 1 d . . . . .
H36 H 0.4096 0.6251 0.8767 0.084 Uiso 1 1 calc R . . . .
C32 C 0.38363(15) 0.8214(3) 0.62353(18) 0.0788(10) Uani 1 1 d . . . . .
H32 H 0.3913 0.7568 0.6479 0.095 Uiso 1 1 calc R . . . .
C23 C 0.25707(18) 0.8142(4) 0.3591(2) 0.0955(14) Uani 1 1 d . . . . .
H23 H 0.2525 0.8827 0.3389 0.115 Uiso 1 1 calc R . . . .
C41 C 0.19303(14) 0.2029(3) 0.59047(15) 0.0743(10) Uani 1 1 d . . . . .
H41 H 0.1611 0.1534 0.5744 0.089 Uiso 1 1 calc R . . . .
C42 C 0.22177(14) 0.2111(3) 0.56169(14) 0.0724(9) Uani 1 1 d . . . . .
H42 H 0.2093 0.1665 0.5259 0.087 Uiso 1 1 calc R . . . .
C24 C 0.22944(18) 0.7203(6) 0.32263(19) 0.1133(18) Uani 1 1 d . . . . .
H24 H 0.2062 0.7242 0.2778 0.136 Uiso 1 1 calc R . . . .
C29 C 0.3615(2) 1.0151(3) 0.5536(3) 0.1123(16) Uani 1 1 d . . . . .
H29 H 0.3540 1.0803 0.5297 0.135 Uiso 1 1 calc R . . . .
C31 C 0.4024(2) 0.9258(4) 0.6544(2) 0.1140(14) Uani 1 1 d . . . . .
H31 H 0.4230 0.9306 0.6990 0.137 Uiso 1 1 calc R . . . .
C25 C 0.23652(16) 0.6191(4) 0.35326(19) 0.1038(13) Uani 1 1 d . . . . .
H25 H 0.2182 0.5541 0.3289 0.125 Uiso 1 1 calc R . . . .
C30 C 0.3905(3) 1.0208(4) 0.6188(3) 0.1361(19) Uani 1 1 d . . . . .
H30 H 0.4022 1.0908 0.6392 0.163 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4818(16) . ?
P1 C1 1.782(2) . ?
P1 C8 1.752(2) . ?
P1 C9 1.795(2) . ?
O1 C6 1.382(3) . ?
O1 C7 1.375(3) . ?
O3 C39 1.380(3) . ?
O3 C38 1.378(3) . ?
N1 C44 1.401(3) . ?
N1 C19 1.441(3) . ?
N1 C33 1.405(3) . ?
N2 C17 1.435(3) . ?
N2 C27 1.405(3) . ?
N2 C21 1.402(3) . ?
C6 C1 1.390(3) . ?
C6 C5 1.383(3) . ?
C7 C15 1.479(3) . ?
C7 C8 1.336(3) . ?
O4 C22 1.377(4) . ?
O4 C28 1.382(4) . ?
C1 C2 1.393(3) . ?
C15 C16 1.388(3) . ?
C15 C20 1.405(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.391(3) . ?
C9 C10 1.382(3) . ?
C44 C39 1.399(3) . ?
C44 C43 1.374(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C39 C40 1.369(4) . ?
C17 C18 1.383(3) . ?
C19 C20 1.378(3) . ?
C19 C18 1.379(3) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.370(4) . ?
C38 C33 1.400(3) . ?
C38 C37 1.372(4) . ?
C33 C34 1.372(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(4) . ?
C27 C28 1.389(4) . ?
C27 C32 1.375(4) . ?
C21 C22 1.392(4) . ?
C21 C26 1.371(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.369(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.373(4) . ?
C4 H4 0.9300 . ?
C43 H43 0.9300 . ?
C43 C42 1.381(4) . ?
C22 C23 1.358(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(4) . ?
C12 C11 1.374(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.385(4) . ?
C13 H13 0.9300 . ?
C37 H37 0.9300 . ?
C37 C36 1.375(4) . ?
C11 H11 0.9300 . ?
C35 H35 0.9300 . ?
C35 C36 1.377(4) . ?
C28 C29 1.391(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.389(4) . ?
C36 H36 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.393(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.360(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.375(4) . ?
C42 H42 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.383(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.363(6) . ?
C31 H31 0.9300 . ?
C31 C30 1.361(6) . ?
C25 H25 0.9300 . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 C1 114.68(10) . . ?
O2 P1 C8 116.66(10) . . ?
O2 P1 C9 110.47(10) . . ?
C1 P1 C9 107.50(11) . . ?
C8 P1 C1 99.80(11) . . ?
C8 P1 C9 106.83(11) . . ?
C7 O1 C6 122.57(17) . . ?
C38 O3 C39 118.22(18) . . ?
C44 N1 C19 120.7(2) . . ?
C44 N1 C33 119.58(19) . . ?
C33 N1 C19 118.6(2) . . ?
C27 N2 C17 120.8(2) . . ?
C21 N2 C17 119.6(2) . . ?
C21 N2 C27 119.2(2) . . ?
O1 C6 C1 123.9(2) . . ?
O1 C6 C5 114.5(2) . . ?
C5 C6 C1 121.5(2) . . ?
O1 C7 C15 110.23(18) . . ?
C8 C7 O1 124.4(2) . . ?
C8 C7 C15 125.4(2) . . ?
C22 O4 C28 118.0(3) . . ?
C6 C1 P1 122.32(18) . . ?
C6 C1 C2 117.2(2) . . ?
C2 C1 P1 120.43(18) . . ?
C16 C15 C7 120.05(19) . . ?
C16 C15 C20 118.9(2) . . ?
C20 C15 C7 121.0(2) . . ?
P1 C8 H8 117.4 . . ?
C7 C8 P1 125.12(19) . . ?
C7 C8 H8 117.4 . . ?
C14 C9 P1 118.8(2) . . ?
C10 C9 P1 122.24(19) . . ?
C10 C9 C14 118.9(2) . . ?
C39 C44 N1 118.9(2) . . ?
C43 C44 N1 123.3(2) . . ?
C43 C44 C39 117.8(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
O3 C39 C44 121.8(2) . . ?
C40 C39 O3 117.5(2) . . ?
C40 C39 C44 120.7(3) . . ?
C16 C17 N2 119.2(2) . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 N2 120.2(2) . . ?
C20 C19 N1 120.0(2) . . ?
C20 C19 C18 120.7(2) . . ?
C18 C19 N1 119.3(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.2 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
O3 C38 C33 121.7(2) . . ?
C37 C38 O3 117.6(2) . . ?
C37 C38 C33 120.8(3) . . ?
C38 C33 N1 118.9(2) . . ?
C34 C33 N1 123.0(2) . . ?
C34 C33 C38 118.1(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C28 C27 N2 118.9(3) . . ?
C32 C27 N2 123.8(3) . . ?
C32 C27 C28 117.3(3) . . ?
C22 C21 N2 119.1(3) . . ?
C26 C21 N2 122.8(3) . . ?
C26 C21 C22 118.1(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C39 C40 H40 119.5 . . ?
C39 C40 C41 121.0(3) . . ?
C41 C40 H40 119.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C44 C43 H43 119.4 . . ?
C44 C43 C42 121.1(3) . . ?
C42 C43 H43 119.4 . . ?
O4 C22 C21 121.6(3) . . ?
C23 C22 O4 117.1(4) . . ?
C23 C22 C21 121.3(4) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.2(3) . . ?
C35 C34 H34 119.4 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C38 C37 H37 119.8 . . ?
C38 C37 C36 120.3(3) . . ?
C36 C37 H37 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(3) . . ?
C36 C35 H35 120.0 . . ?
O4 C28 C27 121.7(3) . . ?
O4 C28 C29 116.6(4) . . ?
C27 C28 C29 121.6(4) . . ?
C21 C26 H26 119.8 . . ?
C21 C26 C25 120.3(4) . . ?
C25 C26 H26 119.8 . . ?
C37 C36 C35 119.6(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C27 C32 H32 119.2 . . ?
C27 C32 C31 121.6(4) . . ?
C31 C32 H32 119.2 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 120.9(4) . . ?
C24 C23 H23 119.5 . . ?
C40 C41 H41 120.6 . . ?
C40 C41 C42 118.8(3) . . ?
C42 C41 H41 120.6 . . ?
C43 C42 H42 119.7 . . ?
C41 C42 C43 120.6(3) . . ?
C41 C42 H42 119.7 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 119.0(4) . . ?
C25 C24 H24 120.5 . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 119.1(4) . . ?
C30 C29 H29 120.5 . . ?
C32 C31 H31 120.3 . . ?
C30 C31 C32 119.4(5) . . ?
C30 C31 H31 120.3 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.3(4) . . ?
C24 C25 H25 119.8 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.1(5) . . ?
C31 C30 H30 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
