# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_ffe008
_database_code_depnum_ccdc_archive 'CCDC 1898472'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 O P, H2 O2'
_chemical_formula_sum            'C21 H23 O3 P'
_chemical_formula_weight         354.36
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.937(3)
_cell_length_b                   17.920(4)
_cell_length_c                   10.968(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.255(2)
_cell_angle_gamma                90
_cell_volume                     1911.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6608
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.434
_cell_measurement_theta_min      2.273
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0455 after correction.
The Ratio of minimum to maximum transmission is 0.8175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.482
_exptl_crystal_size_min          0.212
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3491
_reflns_number_total             4416
_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    ?
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.032
_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)+(0.0658P)²+0.9658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1316
_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, All O(H) groups
2. Restrained distances
 O3A-O2A \\sim O3-O2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim O2A \\sim O3A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 O2, O3, O2A, O3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O2A)=Sof(H2AA)=Sof(O3A)=Sof(H3AA)=1-FVAR(1)
 Sof(O2)=Sof(H2A)=Sof(O3)=Sof(H3A)=FVAR(1)
6.a Riding coordinates:
 O2(H2A), O3(H3A), O2A(H2AA), O3A(H3AA)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.54846(4) 0.65058(3) 0.25446(4) 0.01720(13) Uani 1 1 d . . . . .
O1 O 0.52573(13) 0.59194(7) 0.14875(13) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.65552(18) 0.62049(10) 0.42639(17) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.79810(19) 0.62082(11) 0.47811(19) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.8382 0.6397 0.4237 0.029 Uiso 1 1 calc R . . . .
C3 C 0.88143(19) 0.59377(11) 0.6083(2) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.9785 0.5945 0.6426 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8252(2) 0.56548(11) 0.68987(19) 0.0274(4) Uani 1 1 d . . . . .
C5 C 0.6839(2) 0.56394(11) 0.63743(19) 0.0275(4) Uani 1 1 d . . . . .
H5 H 0.6441 0.5438 0.6912 0.033 Uiso 1 1 calc R . . . .
C6 C 0.59920(19) 0.59135(10) 0.50735(18) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.5022 0.5903 0.4733 0.027 Uiso 1 1 calc R . . . .
C7 C 0.9177(2) 0.53833(14) 0.8327(2) 0.0424(6) Uani 1 1 d . . . . .
H7A H 0.9537 0.4889 0.8282 0.064 Uiso 1 1 calc GR . . . .
H7B H 0.8653 0.5351 0.8849 0.064 Uiso 1 1 calc GR . . . .
H7C H 0.9943 0.5733 0.8782 0.064 Uiso 1 1 calc GR . . . .
C8 C 0.38812(17) 0.68026(10) 0.24711(17) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.3820(2) 0.74282(11) 0.3194(2) 0.0273(4) Uani 1 1 d . . . . .
H9 H 0.4641 0.7689 0.3767 0.033 Uiso 1 1 calc R . . . .
C10 C 0.2573(2) 0.76737(12) 0.3086(2) 0.0304(4) Uani 1 1 d . . . . .
H10 H 0.2546 0.8100 0.3588 0.036 Uiso 1 1 calc R . . . .
C11 C 0.13627(19) 0.73016(12) 0.2250(2) 0.0293(5) Uani 1 1 d . . . . .
C12 C 0.1435(2) 0.66731(13) 0.1559(2) 0.0321(5) Uani 1 1 d . . . . .
H12 H 0.0615 0.6407 0.1003 0.039 Uiso 1 1 calc R . . . .
C13 C 0.26788(19) 0.64192(11) 0.16560(19) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.2704 0.5987 0.1167 0.031 Uiso 1 1 calc R . . . .
C14 C 0.0005(2) 0.75947(15) 0.2084(2) 0.0431(6) Uani 1 1 d . . . . .
H14A H 0.0168 0.7984 0.2769 0.065 Uiso 1 1 calc GR . . . .
H14B H -0.0520 0.7186 0.2214 0.065 Uiso 1 1 calc GR . . . .
H14C H -0.0515 0.7804 0.1163 0.065 Uiso 1 1 calc GR . . . .
C15 C 0.62686(17) 0.73237(10) 0.22672(17) 0.0183(4) Uani 1 1 d . . . . .
C16 C 0.70339(18) 0.78295(10) 0.33076(18) 0.0205(4) Uani 1 1 d . . . . .
H16 H 0.7199 0.7732 0.4222 0.025 Uiso 1 1 calc R . . . .
C17 C 0.75547(18) 0.84735(10) 0.30175(19) 0.0225(4) Uani 1 1 d . . . . .
H17 H 0.8078 0.8812 0.3736 0.027 Uiso 1 1 calc R . . . .
C18 C 0.73179(18) 0.86292(10) 0.1684(2) 0.0228(4) Uani 1 1 d . . . . .
C19 C 0.65578(19) 0.81256(11) 0.06537(19) 0.0237(4) Uani 1 1 d . . . . .
H19 H 0.6389 0.8226 -0.0261 0.028 Uiso 1 1 calc R . . . .
C20 C 0.60406(18) 0.74786(10) 0.09347(18) 0.0212(4) Uani 1 1 d . . . . .
H20 H 0.5528 0.7139 0.0215 0.025 Uiso 1 1 calc R . . . .
C21 C 0.7885(2) 0.93246(12) 0.1365(2) 0.0361(5) Uani 1 1 d . . . . .
H21A H 0.8875 0.9264 0.1681 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.7726 0.9751 0.1834 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.7424 0.9412 0.0373 0.054 Uiso 1 1 calc GR . . . .
O2 O 0.7002(2) 0.5408(2) 0.0466(3) 0.0459(9) Uani 0.753(7) 1 d D U P A 1
H2A H 0.6563 0.5606 0.0853 0.069 Uiso 0.753(7) 1 d R . P A 1
O3 O 0.6002(3) 0.54634(19) -0.0978(3) 0.0431(9) Uani 0.753(7) 1 d D U P A 1
H3A H 0.5716 0.5017 -0.1051 0.065 Uiso 0.753(7) 1 d R . P A 1
O2A O 0.6298(12) 0.5844(5) -0.0436(11) 0.065(3) Uani 0.247(7) 1 d D U P A 2
H2AA H 0.5980 0.5866 0.0140 0.097 Uiso 0.247(7) 1 d R . P A 2
O3A O 0.6818(9) 0.5096(5) -0.0143(13) 0.054(3) Uani 0.247(7) 1 d D U P A 2
H3AA H 0.6175 0.4784 -0.0556 0.082 Uiso 0.247(7) 1 d R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4988(13) . ?
P1 C1 1.7876(18) . ?
P1 C8 1.7986(18) . ?
P1 C15 1.7931(19) . ?
C1 C2 1.394(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.380(3) . ?
C4 C7 1.504(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.392(3) . ?
C8 C13 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C11 C12 1.380(3) . ?
C11 C14 1.505(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.396(2) . ?
C15 C20 1.393(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 C19 1.386(3) . ?
C18 C21 1.503(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 H2A 0.8498 . ?
O2 O3 1.459(4) . ?
O3 H3A 0.8501 . ?
O2A H2AA 0.8501 . ?
O2A O3A 1.434(12) . ?
O3A H3AA 0.8500 . ?

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 C1 113.65(8) . . ?
O1 P1 C8 111.08(8) . . ?
O1 P1 C15 111.39(8) . . ?
C1 P1 C8 106.90(8) . . ?
C1 P1 C15 107.00(8) . . ?
C15 P1 C8 106.43(8) . . ?
C2 C1 P1 119.88(14) . . ?
C6 C1 P1 121.21(14) . . ?
C6 C1 C2 118.74(16) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.99(18) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 120.19(19) . . ?
C5 C4 C3 118.62(17) . . ?
C5 C4 C7 121.18(19) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.96(18) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.40(17) . . ?
C5 C6 H6 119.8 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 120.83(14) . . ?
C13 C8 P1 119.97(15) . . ?
C13 C8 C9 119.18(17) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.58(18) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C14 120.1(2) . . ?
C12 C11 C10 118.57(18) . . ?
C12 C11 C14 121.3(2) . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.64(19) . . ?
C13 C12 H12 119.2 . . ?
C8 C13 C12 119.50(19) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 123.11(13) . . ?
C20 C15 P1 118.10(13) . . ?
C20 C15 C16 118.70(17) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.54(16) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.64(17) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C21 120.84(18) . . ?
C19 C18 C17 118.66(17) . . ?
C19 C18 C21 120.50(18) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.13(17) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.33(16) . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 O2 H2A 101.5 . . ?
O2 O3 H3A 95.7 . . ?
O3A O2A H2AA 97.6 . . ?
O2A O3A H3AA 110.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.85 1.94 2.773(3) 168.0 .
O3 H3A O1 0.85 1.93 2.765(3) 169.0 3_665
O2A H2AA O1 0.85 1.97 2.822(10) 179.5 .
O3A H3AA O1 0.85 1.90 2.752(10) 179.4 3_665

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 C1 C2 C3 -176.41(15) . . . . ?
P1 C1 C6 C5 175.92(14) . . . . ?
P1 C8 C9 C10 177.13(15) . . . . ?
P1 C8 C13 C12 -177.18(14) . . . . ?
P1 C15 C16 C17 -176.53(14) . . . . ?
P1 C15 C20 C19 176.31(14) . . . . ?
O1 P1 C1 C2 81.04(16) . . . . ?
O1 P1 C1 C6 -94.19(16) . . . . ?
O1 P1 C8 C9 -169.02(14) . . . . ?
O1 P1 C8 C13 9.13(17) . . . . ?
O1 P1 C15 C16 -156.12(14) . . . . ?
O1 P1 C15 C20 27.26(16) . . . . ?
C1 P1 C8 C9 66.48(17) . . . . ?
C1 P1 C8 C13 -115.36(15) . . . . ?
C1 P1 C15 C16 -31.36(17) . . . . ?
C1 P1 C15 C20 152.02(14) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 C7 -178.3(2) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C7 C4 C5 C6 177.8(2) . . . . ?
C8 P1 C1 C2 -156.05(15) . . . . ?
C8 P1 C1 C6 28.72(17) . . . . ?
C8 P1 C15 C16 82.67(16) . . . . ?
C8 P1 C15 C20 -93.95(15) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C9 C10 C11 C14 -176.94(19) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C14 C11 C12 C13 176.88(19) . . . . ?
C15 P1 C1 C2 -42.34(17) . . . . ?
C15 P1 C1 C6 142.43(15) . . . . ?
C15 P1 C8 C9 -47.61(17) . . . . ?
C15 P1 C8 C13 130.54(15) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C15 C20 C19 -0.5(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C16 C17 C18 C21 -179.75(18) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 0.5(3) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C21 C18 C19 C20 179.35(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_ffe007
_database_code_depnum_ccdc_archive 'CCDC 1898473'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 O P, H2 O2'
_chemical_formula_sum            'C21 H23 O3 P'
_chemical_formula_weight         354.36
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.133(2)
_cell_length_b                   15.855(4)
_cell_length_c                   12.790(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.117(3)
_cell_angle_gamma                90
_cell_volume                     1817.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6287
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.449
_cell_measurement_theta_min      2.569
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9103.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.772
_exptl_crystal_size_mid          0.582
_exptl_crystal_size_min          0.396
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.655
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3393
_reflns_number_total             4199
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.026
_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)+(0.0487P)²+1.4073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1138
_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, All O(H) groups
2.a Riding coordinates:
 O2(H2), O3(H3A)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.67756(5) 0.49687(3) 0.74229(3) 0.01352(12) Uani 1 1 d . . . . .
O1 O 0.77133(13) 0.49806(7) 0.85243(9) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.67257(18) 0.39430(10) 0.68010(13) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.80468(19) 0.34792(11) 0.68200(13) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.7940(2) 0.27018(11) 0.63102(14) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.8820 0.2381 0.6318 0.026 Uiso 1 1 calc R . . . .
C4 C 0.6586(2) 0.23850(11) 0.57921(15) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.6545 0.1850 0.5452 0.030 Uiso 1 1 calc R . . . .
C5 C 0.5292(2) 0.28413(11) 0.57655(14) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.4360 0.2625 0.5405 0.027 Uiso 1 1 calc R . . . .
C6 C 0.53644(19) 0.36174(11) 0.62692(13) 0.0182(4) Uani 1 1 d . . . . .
H6 H 0.4476 0.3933 0.6253 0.022 Uiso 1 1 calc R . . . .
C7 C 0.95564(19) 0.37996(12) 0.73528(15) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.9648 0.4396 0.7177 0.033 Uiso 1 1 calc GR . . . .
H7B H 1.0334 0.3475 0.7102 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.9671 0.3736 0.8127 0.033 Uiso 1 1 calc GR . . . .
C8 C 0.74889(18) 0.56898(10) 0.65421(13) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.77127(19) 0.65507(11) 0.67967(13) 0.0182(4) Uani 1 1 d . . . . .
C10 C 0.8366(2) 0.70526(11) 0.61207(15) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.8511 0.7636 0.6276 0.027 Uiso 1 1 calc R . . . .
C11 C 0.8812(2) 0.67261(12) 0.52298(15) 0.0237(4) Uani 1 1 d . . . . .
H11 H 0.9286 0.7080 0.4796 0.028 Uiso 1 1 calc R . . . .
C12 C 0.8569(2) 0.58863(12) 0.49704(14) 0.0221(4) Uani 1 1 d . . . . .
H12 H 0.8855 0.5661 0.4351 0.027 Uiso 1 1 calc R . . . .
C13 C 0.79030(19) 0.53757(11) 0.56229(13) 0.0179(3) Uani 1 1 d . . . . .
H13 H 0.7725 0.4799 0.5440 0.021 Uiso 1 1 calc R . . . .
C14 C 0.7269(2) 0.69512(12) 0.77531(15) 0.0269(4) Uani 1 1 d . . . . .
H14A H 0.6307 0.6722 0.7848 0.040 Uiso 1 1 calc GR . . . .
H14B H 0.7181 0.7563 0.7647 0.040 Uiso 1 1 calc GR . . . .
H14C H 0.8029 0.6831 0.8388 0.040 Uiso 1 1 calc GR . . . .
C15 C 0.48548(18) 0.52536(10) 0.74019(13) 0.0155(3) Uani 1 1 d . . . . .
C16 C 0.40554(19) 0.48952(10) 0.81321(13) 0.0179(3) Uani 1 1 d . . . . .
C17 C 0.2598(2) 0.51623(11) 0.81009(15) 0.0219(4) Uani 1 1 d . . . . .
H17 H 0.2049 0.4930 0.8592 0.026 Uiso 1 1 calc R . . . .
C18 C 0.1926(2) 0.57575(12) 0.73730(15) 0.0232(4) Uani 1 1 d . . . . .
H18 H 0.0932 0.5934 0.7375 0.028 Uiso 1 1 calc R . . . .
C19 C 0.2696(2) 0.60949(11) 0.66447(14) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.2231 0.6496 0.6136 0.026 Uiso 1 1 calc R . . . .
C20 C 0.41544(19) 0.58442(11) 0.66613(13) 0.0177(3) Uani 1 1 d . . . . .
H20 H 0.4686 0.6078 0.6161 0.021 Uiso 1 1 calc R . . . .
C21 C 0.4716(2) 0.42269(12) 0.89238(15) 0.0252(4) Uani 1 1 d . . . . .
H21A H 0.5013 0.3739 0.8542 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.3971 0.4051 0.9339 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.5592 0.4456 0.9404 0.038 Uiso 1 1 calc GR . . . .
O2 O 0.92171(18) 0.60505(10) 1.00283(12) 0.0436(4) Uani 1 1 d . . . . .
H2 H 0.8817 0.5710 0.9461 0.065 Uiso 1 1 d R . . . .
O3 O 1.0731(2) 0.61057(10) 0.98996(13) 0.0440(4) Uani 1 1 d . . . . .
H3A H 1.1129 0.5697 1.0422 0.066 Uiso 1 1 d 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 O1 1.5011(12) . ?
P1 C1 1.8071(17) . ?
P1 C8 1.8121(17) . ?
P1 C15 1.8068(18) . ?
C1 C2 1.409(2) . ?
C1 C6 1.396(2) . ?
C2 C3 1.389(2) . ?
C2 C7 1.504(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.409(2) . ?
C8 C13 1.394(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.502(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.411(2) . ?
C15 C20 1.396(2) . ?
C16 C17 1.390(3) . ?
C16 C21 1.509(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 H2 0.9217 . ?
O2 O3 1.426(2) . ?
O3 H3A 0.9509 . ?

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 C1 112.70(7) . . ?
O1 P1 C8 111.53(7) . . ?
O1 P1 C15 112.80(7) . . ?
C1 P1 C8 106.01(8) . . ?
C15 P1 C1 106.05(8) . . ?
C15 P1 C8 107.30(8) . . ?
C2 C1 P1 120.87(13) . . ?
C6 C1 P1 119.46(13) . . ?
C6 C1 C2 119.65(15) . . ?
C1 C2 C7 122.60(15) . . ?
C3 C2 C1 118.20(16) . . ?
C3 C2 C7 119.19(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.58(17) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.32(17) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.34(17) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.90(16) . . ?
C5 C6 H6 119.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 121.40(13) . . ?
C13 C8 P1 119.16(13) . . ?
C13 C8 C9 119.34(16) . . ?
C8 C9 C14 123.23(16) . . ?
C10 C9 C8 118.09(16) . . ?
C10 C9 C14 118.68(16) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.85(17) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.02(17) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.23(17) . . ?
C13 C12 H12 120.4 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.43(17) . . ?
C12 C13 H13 119.3 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 120.95(13) . . ?
C20 C15 P1 119.62(13) . . ?
C20 C15 C16 119.42(16) . . ?
C15 C16 C21 122.42(16) . . ?
C17 C16 C15 118.24(16) . . ?
C17 C16 C21 119.34(16) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.69(17) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.09(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.49(17) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.05(16) . . ?
C19 C20 H20 119.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 O2 H2 101.0 . . ?
O2 O3 H3A 97.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.92 1.82 2.7286(19) 167.0 .
O3 H3A O1 0.95 1.88 2.819(2) 168.0 3_767

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 C1 C2 C3 -178.76(13) . . . . ?
P1 C1 C2 C7 0.3(2) . . . . ?
P1 C1 C6 C5 178.65(13) . . . . ?
P1 C8 C9 C10 175.34(13) . . . . ?
P1 C8 C9 C14 -5.2(2) . . . . ?
P1 C8 C13 C12 -174.57(13) . . . . ?
P1 C15 C16 C17 177.73(13) . . . . ?
P1 C15 C16 C21 -3.4(2) . . . . ?
P1 C15 C20 C19 -178.09(13) . . . . ?
O1 P1 C1 C2 -47.08(16) . . . . ?
O1 P1 C1 C6 134.76(13) . . . . ?
O1 P1 C8 C9 -55.34(15) . . . . ?
O1 P1 C8 C13 121.01(13) . . . . ?
O1 P1 C15 C16 -46.83(16) . . . . ?
O1 P1 C15 C20 132.42(13) . . . . ?
C1 P1 C8 C9 -178.35(13) . . . . ?
C1 P1 C8 C13 -2.00(15) . . . . ?
C1 P1 C15 C16 76.98(15) . . . . ?
C1 P1 C15 C20 -103.77(14) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 C2 C7 178.42(16) . . . . ?
C7 C2 C3 C4 -178.80(17) . . . . ?
C8 P1 C1 C2 75.19(15) . . . . ?
C8 P1 C1 C6 -102.98(14) . . . . ?
C8 P1 C15 C16 -170.06(13) . . . . ?
C8 P1 C15 C20 9.19(16) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C9 C8 C13 C12 1.9(2) . . . . ?
C9 C10 C11 C12 2.1(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
C13 C8 C9 C14 178.44(16) . . . . ?
C14 C9 C10 C11 179.57(17) . . . . ?
C15 P1 C1 C2 -170.95(13) . . . . ?
C15 P1 C1 C6 10.89(16) . . . . ?
C15 P1 C8 C9 68.66(15) . . . . ?
C15 P1 C8 C13 -114.99(14) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C15 C20 C19 1.2(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C20 C15 C16 C17 -1.5(2) . . . . ?
C20 C15 C16 C21 177.36(16) . . . . ?
C21 C16 C17 C18 -178.35(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_fe011
_database_code_depnum_ccdc_archive 'CCDC 1898476'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C19 H17 O P), 0.5(H2 O2)'
_chemical_formula_sum            'C19 H18 O2 P'
_chemical_formula_weight         309.30
_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'
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                   8.606(3)
_cell_length_b                   10.259(3)
_cell_length_c                   18.844(6)
_cell_angle_alpha                94.697(5)
_cell_angle_beta                 90.536(5)
_cell_angle_gamma                102.113(5)
_cell_volume                     1620.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.613
_cell_measurement_theta_min      2.225
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8995.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.226
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34408
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         1.085
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6449
_reflns_number_total             7421
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7421
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.268
_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)+2.8388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1259
_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, All O(H) groups
2. Restrained distances
 O4-O3 \\sim O4A-O3A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
O3 \\sim H3A \\sim O4 \\sim H4A \\sim O4A \\sim O3A: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
 O3, H3A, O4, H4A, O4A, O3A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(H19)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(1)
 Sof(H2)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(1)
 Sof(O3A)=Sof(H3AA)=Sof(O4A)=Sof(H4AA)=1-FVAR(2)
 Sof(O3)=Sof(H3A)=Sof(O4)=Sof(H4A)=FVAR(2)
6.a Riding coordinates:
 C2(H2), C19(H19), O3(H3A), O4(H4A), O3A(H3AA), O4A(H4AA)
6.b Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24),
  C25(H25), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C36(H36), C37(H37), C38(H38)
6.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.78297(7) 0.73266(6) 0.40590(3) 0.01827(13) Uani 1 1 d . . . . .
O1 O 0.6740(2) 0.61838(18) 0.36433(9) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.9900(3) 0.7303(2) 0.39628(12) 0.0202(5) Uani 1 1 d . . . . .
C2 C 1.0409(3) 0.6101(3) 0.39758(16) 0.0330(6) Uani 1 1 d . . . . .
H2 H 0.9691 0.5307 0.4036 0.040 Uiso 0.760(4) 1 d R . P A .
C3 C 1.2025(4) 0.6120(3) 0.38954(19) 0.0451(8) Uani 1 1 d . . . . .
H3 H 1.2387 0.5307 0.3896 0.054 Uiso 1 1 calc R . . . .
C4 C 1.3099(3) 0.7288(4) 0.38152(16) 0.0389(7) Uani 1 1 d . . . . .
H4 H 1.4189 0.7271 0.3754 0.047 Uiso 1 1 calc R . . . .
C5 C 1.2618(3) 0.8474(3) 0.38216(15) 0.0348(7) Uani 1 1 d . . . . .
H5 H 1.3369 0.9285 0.3780 0.042 Uiso 1 1 calc R . . . .
C6 C 1.1006(3) 0.8478(3) 0.38899(15) 0.0280(6) Uani 1 1 d . . . . .
H6 H 1.0661 0.9298 0.3887 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9295(5) 0.4776(3) 0.4113(2) 0.0389(9) Uani 0.760(4) 1 d . . P A 1
H7A H 0.9899 0.4064 0.4099 0.058 Uiso 0.760(4) 1 calc R . P A 1
H7B H 0.8829 0.4863 0.4583 0.058 Uiso 0.760(4) 1 calc R . P A 1
H7C H 0.8446 0.4553 0.3746 0.058 Uiso 0.760(4) 1 calc R . P A 1
C8 C 0.7465(3) 0.7324(2) 0.50006(13) 0.0195(5) Uani 1 1 d . . . . .
C9 C 0.8610(3) 0.7957(3) 0.55200(13) 0.0242(5) Uani 1 1 d . . . . .
H9 H 0.9625 0.8409 0.5380 0.029 Uiso 1 1 calc R . . . .
C10 C 0.8266(3) 0.7928(3) 0.62416(14) 0.0279(6) Uani 1 1 d . . . . .
H10 H 0.9043 0.8369 0.6592 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6792(3) 0.7257(3) 0.64479(14) 0.0280(6) Uani 1 1 d . . . . .
H11 H 0.6558 0.7237 0.6939 0.034 Uiso 1 1 calc R . . . .
C12 C 0.5660(3) 0.6613(3) 0.59356(14) 0.0259(5) Uani 1 1 d . . . . .
H12 H 0.4657 0.6141 0.6079 0.031 Uiso 1 1 calc R . . . .
C13 C 0.5980(3) 0.6654(2) 0.52147(13) 0.0221(5) Uani 1 1 d . . . . .
H13 H 0.5189 0.6227 0.4868 0.026 Uiso 1 1 calc R . . . .
C14 C 0.7556(3) 0.8919(2) 0.37948(13) 0.0205(5) Uani 1 1 d . . . . .
C15 C 0.7161(3) 0.9888(3) 0.42797(14) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.7088 0.9743 0.4771 0.032 Uiso 1 1 calc R . . . .
C16 C 0.6872(3) 1.1067(3) 0.40465(17) 0.0346(6) Uani 1 1 d . . . . .
H16 H 0.6607 1.1729 0.4378 0.042 Uiso 1 1 calc R . . . .
C17 C 0.6972(3) 1.1272(3) 0.33321(17) 0.0348(7) Uani 1 1 d . . . . .
H17 H 0.6769 1.2077 0.3173 0.042 Uiso 1 1 calc R . . . .
C18 C 0.7367(3) 1.0315(3) 0.28457(16) 0.0347(7) Uani 1 1 d . . . . .
H18 H 0.7435 1.0469 0.2356 0.042 Uiso 1 1 calc R . . . .
C19 C 0.7663(3) 0.9131(3) 0.30696(15) 0.0292(6) Uani 1 1 d . . . . .
H19 H 0.7933 0.8491 0.2743 0.035 Uiso 0.240(4) 1 d R . P A 1
P2 P 0.20296(8) 0.21516(7) 0.13255(3) 0.02444(15) Uani 1 1 d . . . . .
O2 O 0.3157(2) 0.3067(2) 0.18488(10) 0.0311(4) Uani 1 1 d . . . . .
C20 C 0.2702(3) 0.2245(3) 0.04168(13) 0.0240(5) Uani 1 1 d . . . . .
C21 C 0.2851(3) 0.3454(3) 0.00898(14) 0.0278(6) Uani 1 1 d . . . . .
C22 C 0.3510(3) 0.3501(3) -0.05863(15) 0.0327(6) Uani 1 1 d . . . . .
H22 H 0.3615 0.4302 -0.0819 0.039 Uiso 1 1 calc R . . . .
C23 C 0.4017(3) 0.2419(3) -0.09299(15) 0.0346(6) Uani 1 1 d . . . . .
H23 H 0.4467 0.2488 -0.1387 0.041 Uiso 1 1 calc R . . . .
C24 C 0.3864(3) 0.1246(3) -0.06055(14) 0.0310(6) Uani 1 1 d . . . . .
H24 H 0.4207 0.0502 -0.0837 0.037 Uiso 1 1 calc R . . . .
C25 C 0.3202(3) 0.1161(3) 0.00649(14) 0.0265(5) Uani 1 1 d . . . . .
H25 H 0.3089 0.0349 0.0287 0.032 Uiso 1 1 calc R . . . .
C26 C 0.2339(4) 0.4672(3) 0.04339(16) 0.0377(7) Uani 1 1 d . . . . .
H26A H 0.1176 0.4499 0.0447 0.056 Uiso 1 1 calc GR . . . .
H26B H 0.2723 0.5439 0.0158 0.056 Uiso 1 1 calc GR . . . .
H26C H 0.2785 0.4870 0.0921 0.056 Uiso 1 1 calc GR . . . .
C27 C 0.1840(3) 0.0437(3) 0.15217(14) 0.0280(6) Uani 1 1 d . . . . .
C28 C 0.0521(4) -0.0567(3) 0.1317(2) 0.0488(9) Uani 1 1 d . . . . .
H28 H -0.0352 -0.0359 0.1071 0.059 Uiso 1 1 calc R . . . .
C29 C 0.0480(5) -0.1871(4) 0.1471(2) 0.0619(11) Uani 1 1 d . . . . .
H29 H -0.0425 -0.2553 0.1334 0.074 Uiso 1 1 calc R . . . .
C30 C 0.1753(4) -0.2184(3) 0.18251(19) 0.0479(8) Uani 1 1 d . . . . .
H30 H 0.1733 -0.3083 0.1919 0.058 Uiso 1 1 calc R . . . .
C31 C 0.3046(4) -0.1191(3) 0.20401(15) 0.0341(6) Uani 1 1 d . . . . .
H31 H 0.3911 -0.1404 0.2290 0.041 Uiso 1 1 calc R . . . .
C32 C 0.3093(3) 0.0119(3) 0.18937(14) 0.0290(6) Uani 1 1 d . . . . .
H32 H 0.3985 0.0803 0.2048 0.035 Uiso 1 1 calc R . . . .
C33 C 0.0074(3) 0.2526(3) 0.13483(15) 0.0283(6) Uani 1 1 d . . . . .
C34 C -0.0294(4) 0.3313(3) 0.19386(16) 0.0372(7) Uani 1 1 d . . . . .
H34 H 0.0464 0.3613 0.2318 0.045 Uiso 1 1 calc R . . . .
C35 C -0.1771(4) 0.3651(3) 0.19668(19) 0.0457(8) Uani 1 1 d . . . . .
H35 H -0.2019 0.4197 0.2363 0.055 Uiso 1 1 calc R . . . .
C36 C -0.2879(4) 0.3199(3) 0.1422(2) 0.0476(9) Uani 1 1 d . . . . .
H36 H -0.3896 0.3421 0.1451 0.057 Uiso 1 1 calc R . . . .
C37 C -0.2527(4) 0.2423(3) 0.0833(2) 0.0472(9) Uani 1 1 d . . . . .
H37 H -0.3297 0.2120 0.0459 0.057 Uiso 1 1 calc R . . . .
C38 C -0.1038(3) 0.2090(3) 0.07913(17) 0.0362(7) Uani 1 1 d . . . . .
H38 H -0.0784 0.1569 0.0386 0.043 Uiso 1 1 calc R . . . .
O3 O 0.5809(4) 0.5809(3) 0.22647(15) 0.0530(8) Uani 0.917(5) 1 d D U P B 1
H3A H 0.5968 0.5950 0.2713 0.079 Uiso 0.917(5) 1 d R U P B 1
O4 O 0.4127(4) 0.5719(3) 0.22648(17) 0.0548(8) Uani 0.917(5) 1 d D U P B 1
H4A H 0.3805 0.4894 0.2132 0.082 Uiso 0.917(5) 1 d R U P B 1
C7A C 0.8350(15) 0.8418(11) 0.2595(8) 0.0389(9) Uani 0.240(4) 1 d . . P A 2
H7AA H 0.8512 0.7606 0.2799 0.058 Uiso 0.240(4) 1 calc R . P A 2
H7AB H 0.7666 0.8170 0.2166 0.058 Uiso 0.240(4) 1 calc R . P A 2
H7AC H 0.9379 0.8952 0.2471 0.058 Uiso 0.240(4) 1 calc R . P A 2
O3A O 0.466(5) 0.615(3) 0.2582(17) 0.062(3) Uani 0.083(5) 1 d D U P B 2
H3AA H 0.5323 0.6162 0.2921 0.093 Uiso 0.083(5) 1 d R . P B 2
O4A O 0.514(5) 0.531(4) 0.2018(17) 0.065(3) Uani 0.083(5) 1 d D U P B 2
H4AA H 0.4481 0.4566 0.1961 0.097 Uiso 0.083(5) 1 d R . P B 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 O1 1.4976(18) . ?
P1 C1 1.797(2) . ?
P1 C8 1.805(3) . ?
P1 C14 1.807(2) . ?
C1 C2 1.394(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C2 C7 1.533(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.371(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C6 H6 0.9500 . ?
C7 H2 0.6082 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.400(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.396(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 C19 1.402(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C19 H19 0.9301 . ?
C19 C7A 1.330(13) . ?
P2 O2 1.4980(19) . ?
P2 C20 1.816(3) . ?
P2 C27 1.801(3) . ?
P2 C33 1.803(3) . ?
C20 C21 1.412(4) . ?
C20 C25 1.395(4) . ?
C21 C22 1.400(4) . ?
C21 C26 1.511(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(4) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.391(4) . ?
C27 C32 1.389(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.385(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.374(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.398(4) . ?
C33 C38 1.394(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.387(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.377(5) . ?
C36 H36 0.9500 . ?
C36 C37 1.386(5) . ?
C37 H37 0.9500 . ?
C37 C38 1.395(4) . ?
C38 H38 0.9500 . ?
O3 H3A 0.8500 . ?
O3 O4 1.431(4) . ?
O4 H4A 0.8499 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
O3A H3AA 0.8500 . ?
O3A O4A 1.431(6) . ?
O4A H4AA 0.8498 . ?

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 C1 113.54(11) . . ?
O1 P1 C8 111.40(11) . . ?
O1 P1 C14 111.46(11) . . ?
C1 P1 C8 106.26(11) . . ?
C1 P1 C14 107.00(11) . . ?
C8 P1 C14 106.78(11) . . ?
C2 C1 P1 120.0(2) . . ?
C6 C1 P1 120.55(19) . . ?
C6 C1 C2 119.5(2) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 C7 123.1(3) . . ?
C3 C2 H2 120.8 . . ?
C3 C2 C7 118.4(3) . . ?
C7 C2 H2 3.6 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 H2 5.6 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H2 C7 H7A 112.8 . . ?
H2 C7 H7B 111.5 . . ?
H2 C7 H7C 104.0 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 122.58(19) . . ?
C13 C8 P1 118.29(19) . . ?
C13 C8 C9 119.1(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C15 C14 P1 122.02(19) . . ?
C15 C14 C19 120.1(2) . . ?
C19 C14 P1 117.82(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 119.0(3) . . ?
C18 C19 H19 120.4 . . ?
C7A C19 C14 124.1(6) . . ?
C7A C19 C18 115.3(6) . . ?
O2 P2 C20 112.39(12) . . ?
O2 P2 C27 110.47(12) . . ?
O2 P2 C33 111.62(13) . . ?
C27 P2 C20 106.57(13) . . ?
C27 P2 C33 107.81(12) . . ?
C33 P2 C20 107.73(12) . . ?
C21 C20 P2 119.9(2) . . ?
C25 C20 P2 119.9(2) . . ?
C25 C20 C21 119.9(2) . . ?
C20 C21 C26 123.3(2) . . ?
C22 C21 C20 117.3(3) . . ?
C22 C21 C26 119.5(3) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 C21 122.3(3) . . ?
C23 C22 H22 118.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(3) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.3(3) . . ?
C24 C25 H25 119.4 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 P2 123.4(2) . . ?
C32 C27 P2 117.4(2) . . ?
C32 C27 C28 119.2(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(3) . . ?
C32 C31 H31 119.9 . . ?
C27 C32 H32 119.9 . . ?
C31 C32 C27 120.3(3) . . ?
C31 C32 H32 119.9 . . ?
C34 C33 P2 117.9(2) . . ?
C38 C33 P2 122.0(2) . . ?
C38 C33 C34 120.1(3) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 C33 119.6(3) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 H35 119.9 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C35 C36 H36 119.7 . . ?
C35 C36 C37 120.7(3) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.8(3) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 119.6(3) . . ?
C33 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
O4 O3 H3A 97.0 . . ?
O3 O4 H4A 100.0 . . ?
C19 C7A H7AA 109.5 . . ?
C19 C7A H7AB 109.5 . . ?
C19 C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O4A O3A H3AA 104.3 . . ?
O3A O4A H4AA 110.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1 0.85 1.85 2.684(3) 167.7 .
O4 H4A O2 0.85 1.87 2.720(4) 178.2 .
O3A H3AA O1 0.85 1.81 2.67(4) 179.9 .
O4A H4AA O2 0.85 1.71 2.56(4) 179.9 .

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 C1 C2 C3 179.6(2) . . . . ?
P1 C1 C2 C7 -3.7(4) . . . . ?
P1 C1 C6 C5 179.4(2) . . . . ?
P1 C8 C9 C10 179.86(19) . . . . ?
P1 C8 C13 C12 179.11(19) . . . . ?
P1 C14 C15 C16 -176.3(2) . . . . ?
P1 C14 C19 C18 176.3(2) . . . . ?
P1 C14 C19 C7A -18.6(8) . . . . ?
O1 P1 C1 C2 -42.5(2) . . . . ?
O1 P1 C1 C6 138.9(2) . . . . ?
O1 P1 C8 C9 157.5(2) . . . . ?
O1 P1 C8 C13 -22.2(2) . . . . ?
O1 P1 C14 C15 122.7(2) . . . . ?
O1 P1 C14 C19 -53.6(2) . . . . ?
C1 P1 C8 C9 33.3(2) . . . . ?
C1 P1 C8 C13 -146.32(19) . . . . ?
C1 P1 C14 C15 -112.6(2) . . . . ?
C1 P1 C14 C19 71.0(2) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -1.9(5) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C6 C1 C2 C7 175.0(3) . . . . ?
C7 C2 C3 C4 -175.9(3) . . . . ?
C8 P1 C1 C2 80.3(2) . . . . ?
C8 P1 C1 C6 -98.3(2) . . . . ?
C8 P1 C14 C15 0.8(2) . . . . ?
C8 P1 C14 C19 -175.5(2) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 C8 1.3(4) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?
C14 P1 C1 C2 -165.9(2) . . . . ?
C14 P1 C1 C6 15.5(2) . . . . ?
C14 P1 C8 C9 -80.6(2) . . . . ?
C14 P1 C8 C13 99.7(2) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C14 C19 C18 -0.1(4) . . . . ?
C15 C14 C19 C7A 165.0(7) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C17 C18 C19 C7A -166.4(7) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
P2 C20 C21 C22 174.4(2) . . . . ?
P2 C20 C21 C26 -5.6(4) . . . . ?
P2 C20 C25 C24 -173.9(2) . . . . ?
P2 C27 C28 C29 178.3(3) . . . . ?
P2 C27 C32 C31 -177.8(2) . . . . ?
P2 C33 C34 C35 178.3(2) . . . . ?
P2 C33 C38 C37 -179.2(2) . . . . ?
O2 P2 C20 C21 -63.5(2) . . . . ?
O2 P2 C20 C25 111.0(2) . . . . ?
O2 P2 C27 C28 155.9(3) . . . . ?
O2 P2 C27 C32 -24.4(3) . . . . ?
O2 P2 C33 C34 -16.6(3) . . . . ?
O2 P2 C33 C38 161.5(2) . . . . ?
C20 P2 C27 C28 -81.7(3) . . . . ?
C20 P2 C27 C32 97.9(2) . . . . ?
C20 P2 C33 C34 -140.4(2) . . . . ?
C20 P2 C33 C38 37.7(3) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C20 C25 C24 0.6(4) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C23 C24 C25 C20 -0.5(4) . . . . ?
C25 C20 C21 C22 -0.1(4) . . . . ?
C25 C20 C21 C26 180.0(3) . . . . ?
C26 C21 C22 C23 179.5(3) . . . . ?
C27 P2 C20 C21 175.4(2) . . . . ?
C27 P2 C20 C25 -10.2(2) . . . . ?
C27 P2 C33 C34 104.9(2) . . . . ?
C27 P2 C33 C38 -77.0(2) . . . . ?
C27 C28 C29 C30 -0.5(6) . . . . ?
C28 C27 C32 C31 1.9(4) . . . . ?
C28 C29 C30 C31 1.7(6) . . . . ?
C29 C30 C31 C32 -1.1(5) . . . . ?
C30 C31 C32 C27 -0.7(4) . . . . ?
C32 C27 C28 C29 -1.3(5) . . . . ?
C33 P2 C20 C21 59.9(2) . . . . ?
C33 P2 C20 C25 -125.7(2) . . . . ?
C33 P2 C27 C28 33.7(3) . . . . ?
C33 P2 C27 C32 -146.7(2) . . . . ?
C33 C34 C35 C36 1.0(4) . . . . ?
C34 C33 C38 C37 -1.1(4) . . . . ?
C34 C35 C36 C37 -1.3(5) . . . . ?
C35 C36 C37 C38 0.4(5) . . . . ?
C36 C37 C38 C33 0.9(5) . . . . ?
C38 C33 C34 C35 0.2(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_ffe010
_database_code_depnum_ccdc_archive 'CCDC 1898474'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2016-06-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 O P, H2 O2'
_chemical_formula_sum            'C20 H21 O3 P'
_chemical_formula_weight         340.34
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9873(5)
_cell_length_b                   15.7070(7)
_cell_length_c                   12.4419(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.431(2)
_cell_angle_gamma                90
_cell_volume                     1727.32(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9729
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.577
_cell_measurement_theta_min      2.594
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7411
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1232 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.9386.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.133
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            68772
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.628
_diffrn_reflns_theta_min         2.110
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3096
_reflns_number_total             4000
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.096
_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)+(0.0461P)²+1.8142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1325
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O2 \\sim O3 \\sim O2A \\sim O3A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 O2, O3, O2A, O3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O2A)=Sof(H2A)=Sof(O3A)=Sof(H3AA)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(O3)=Sof(H3A)=FVAR(1)
5.a Riding coordinates:
 O2(H2), O3(H3A), O2A(H2A), O3A(H3AA)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.67811(6) 0.50012(3) 0.25155(4) 0.01983(15) Uani 1 1 d . . . . .
O1 O 0.77299(17) 0.50161(9) 0.36434(12) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.4803(2) 0.52188(13) 0.24852(17) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.3996(3) 0.47961(14) 0.31961(18) 0.0279(5) Uani 1 1 d . . . . .
C3 C 0.2476(3) 0.50022(16) 0.3133(2) 0.0353(6) Uani 1 1 d . . . . .
H3 H 0.1913 0.4731 0.3613 0.042 Uiso 1 1 calc R . . . .
C4 C 0.1763(3) 0.55978(17) 0.2382(2) 0.0383(6) Uani 1 1 d . . . . .
H4 H 0.0726 0.5730 0.2357 0.046 Uiso 1 1 calc R . . . .
C5 C 0.2553(3) 0.59958(16) 0.1676(2) 0.0345(6) Uani 1 1 d . . . . .
H5 H 0.2063 0.6397 0.1159 0.041 Uiso 1 1 calc R . . . .
C6 C 0.4065(2) 0.58070(14) 0.17264(17) 0.0271(5) Uani 1 1 d . . . . .
H6 H 0.4612 0.6080 0.1239 0.033 Uiso 1 1 calc R . . . .
C7 C 0.4712(3) 0.41322(15) 0.4008(2) 0.0350(5) Uani 1 1 d . . . . .
H7A H 0.5031 0.3644 0.3614 0.053 Uiso 1 1 calc GR . . . .
H7B H 0.3975 0.3944 0.4450 0.053 Uiso 1 1 calc GR . . . .
H7C H 0.5594 0.4378 0.4485 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.6847(2) 0.39713(12) 0.18821(17) 0.0212(4) Uani 1 1 d . . . . .
C9 C 0.5603(2) 0.36450(13) 0.11765(17) 0.0245(4) Uani 1 1 d . . . . .
H9 H 0.4683 0.3957 0.1035 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5707(3) 0.28587(14) 0.06768(18) 0.0296(5) Uani 1 1 d . . . . .
H10 H 0.4856 0.2633 0.0196 0.035 Uiso 1 1 calc R . . . .
C11 C 0.7051(3) 0.24063(14) 0.08806(19) 0.0309(5) Uani 1 1 d . . . . .
H11 H 0.7122 0.1873 0.0534 0.037 Uiso 1 1 calc R . . . .
C12 C 0.8288(3) 0.27276(14) 0.1586(2) 0.0316(5) Uani 1 1 d . . . . .
H12 H 0.9204 0.2412 0.1729 0.038 Uiso 1 1 calc R . . . .
C13 C 0.8198(3) 0.35082(14) 0.2087(2) 0.0293(5) Uani 1 1 d . . . . .
H13 H 0.9053 0.3729 0.2569 0.035 Uiso 1 1 calc R . . . .
C14 C 0.7467(2) 0.57621(13) 0.16205(16) 0.0219(4) Uani 1 1 d . . . . .
C15 C 0.7632(2) 0.66358(13) 0.19056(17) 0.0257(5) Uani 1 1 d . . . . .
C16 C 0.8321(3) 0.71695(14) 0.12453(19) 0.0296(5) Uani 1 1 d . . . . .
H16 H 0.8441 0.7756 0.1428 0.035 Uiso 1 1 calc R . . . .
C17 C 0.8836(3) 0.68715(14) 0.03323(19) 0.0305(5) Uani 1 1 d . . . . .
H17 H 0.9325 0.7248 -0.0091 0.037 Uiso 1 1 calc R . . . .
C18 C 0.8638(2) 0.60226(15) 0.00366(18) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.8964 0.5817 -0.0601 0.034 Uiso 1 1 calc R . . . .
C19 C 0.7957(2) 0.54723(13) 0.06807(17) 0.0238(4) Uani 1 1 d . . . . .
H19 H 0.7823 0.4890 0.0478 0.029 Uiso 1 1 calc R . . . .
C20 C 0.7072(3) 0.70110(15) 0.2871(2) 0.0372(6) Uani 1 1 d . . . . .
H20A H 0.5963 0.6996 0.2738 0.056 Uiso 1 1 calc GR . . . .
H20B H 0.7418 0.7602 0.2976 0.056 Uiso 1 1 calc GR . . . .
H20C H 0.7468 0.6679 0.3527 0.056 Uiso 1 1 calc GR . . . .
O2 O 1.0779(7) 0.3958(2) 0.4790(3) 0.0356(12) Uani 0.541(10) 1 d . U P A 1
H2 H 1.1249 0.4281 0.5285 0.053 Uiso 0.541(10) 1 d R . P A 1
O3 O 0.9303(6) 0.3835(3) 0.5056(5) 0.0391(14) Uani 0.541(10) 1 d . U P A 1
H3A H 0.8822 0.4197 0.4619 0.059 Uiso 0.541(10) 1 d R . P A 1
O2A O 0.9930(8) 0.3911(3) 0.5660(7) 0.0508(18) Uani 0.459(10) 1 d . U P A 2
H2A H 1.0664 0.4248 0.5873 0.076 Uiso 0.459(10) 1 d R . P A 2
O3A O 0.9908(10) 0.3855(3) 0.4599(6) 0.0487(18) Uani 0.459(10) 1 d . U P A 2
H3AA H 0.9244 0.4209 0.4300 0.06(2) Uiso 0.459(10) 1 d R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.5045(15) . ?
P1 C1 1.804(2) . ?
P1 C8 1.805(2) . ?
P1 C14 1.816(2) . ?
C1 C2 1.408(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.393(3) . ?
C2 C7 1.512(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.388(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.419(3) . ?
C14 C19 1.398(3) . ?
C15 C16 1.395(3) . ?
C15 C20 1.504(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O2 H2 0.8499 . ?
O2 O3 1.437(9) . ?
O3 H3A 0.8499 . ?
O2A H2A 0.8502 . ?
O2A O3A 1.320(12) . ?
O3A H3AA 0.8501 . ?

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 C1 113.99(9) . . ?
O1 P1 C8 111.30(9) . . ?
O1 P1 C14 111.33(9) . . ?
C1 P1 C8 105.71(9) . . ?
C1 P1 C14 107.78(10) . . ?
C8 P1 C14 106.28(9) . . ?
C2 C1 P1 121.03(16) . . ?
C6 C1 P1 118.96(17) . . ?
C6 C1 C2 120.0(2) . . ?
C1 C2 C7 122.7(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C7 119.5(2) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 121.37(16) . . ?
C9 C8 C13 119.75(19) . . ?
C13 C8 P1 118.85(16) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C15 C14 P1 121.00(16) . . ?
C19 C14 P1 119.47(16) . . ?
C19 C14 C15 119.3(2) . . ?
C14 C15 C20 123.0(2) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 C20 118.9(2) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.0(2) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(2) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.1(2) . . ?
C18 C19 H19 119.4 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 O2 H2 105.8 . . ?
O2 O3 H3A 98.4 . . ?
O3A O2A H2A 102.9 . . ?
O2A O3A H3AA 106.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.85 1.84 2.692(5) 179.8 3_766
O3 H3A O1 0.85 1.91 2.763(5) 179.6 .
O2A H2A O1 0.85 1.86 2.712(7) 179.3 3_766
O3A H3AA O1 0.85 1.93 2.781(6) 179.1 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 179.42(16) . . . . ?
P1 C1 C2 C7 -1.0(3) . . . . ?
P1 C1 C6 C5 -179.77(17) . . . . ?
P1 C8 C9 C10 178.13(16) . . . . ?
P1 C8 C13 C12 -178.21(18) . . . . ?
P1 C14 C15 C16 172.98(16) . . . . ?
P1 C14 C15 C20 -8.2(3) . . . . ?
P1 C14 C19 C18 -173.16(16) . . . . ?
O1 P1 C1 C2 -48.5(2) . . . . ?
O1 P1 C1 C6 132.65(16) . . . . ?
O1 P1 C8 C9 146.32(17) . . . . ?
O1 P1 C8 C13 -35.6(2) . . . . ?
O1 P1 C14 C15 -55.58(19) . . . . ?
O1 P1 C14 C19 119.17(16) . . . . ?
C1 P1 C8 C9 22.1(2) . . . . ?
C1 P1 C8 C13 -159.82(18) . . . . ?
C1 P1 C14 C15 70.12(18) . . . . ?
C1 P1 C14 C19 -115.14(17) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C1 C2 C7 177.9(2) . . . . ?
C7 C2 C3 C4 -178.7(2) . . . . ?
C8 P1 C1 C2 74.06(18) . . . . ?
C8 P1 C1 C6 -104.79(17) . . . . ?
C8 P1 C14 C15 -176.93(16) . . . . ?
C8 P1 C14 C19 -2.19(19) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C8 C13 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 0.4(4) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C14 P1 C1 C2 -172.61(16) . . . . ?
C14 P1 C1 C6 8.55(19) . . . . ?
C14 P1 C8 C9 -92.32(19) . . . . ?
C14 P1 C8 C13 85.81(19) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C19 C18 1.7(3) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C19 -1.7(3) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C19 C14 C15 C16 -1.8(3) . . . . ?
C19 C14 C15 C20 177.0(2) . . . . ?
C20 C15 C16 C17 -178.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_fe363
_database_code_depnum_ccdc_archive 'CCDC 1930449'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-06-17 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 O P, 0.75(H2 O)'
_chemical_formula_sum            'C20 H20.50 O1.75 P'
_chemical_formula_weight         319.83
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7455(6)
_cell_length_b                   15.6756(10)
_cell_length_c                   12.2448(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.131(2)
_cell_angle_gamma                90
_cell_volume                     1661.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      2.988
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1382 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.8218. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.198
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13684
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.688
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2354
_reflns_number_total             2925
_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 V8.38A (Bruker AXS, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.167
_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)+(0.0169P)²+2.1904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1151
_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, All O(H,H) groups
2. Others
 Fixed Sof: O1W(0.75) H1WA(0.75) H1WB(0.75)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.68300(7) 0.50082(4) 0.75673(5) 0.02233(17) Uani 1 1 d . . . . .
O1 O 0.78027(19) 0.49724(11) 0.86672(13) 0.0291(4) Uani 1 1 d . . . . .
C1 C 0.7454(3) 0.42286(15) 0.66335(19) 0.0252(5) Uani 1 1 d . . . . .
C2 C 0.7551(3) 0.33580(16) 0.6926(2) 0.0288(6) Uani 1 1 d . . . . .
C3 C 0.8222(3) 0.28026(16) 0.6245(2) 0.0340(6) Uani 1 1 d . . . . .
H3 H 0.830204 0.221476 0.643318 0.041 Uiso 1 1 calc R . . . .
C4 C 0.8777(3) 0.30796(18) 0.5304(2) 0.0363(6) Uani 1 1 d . . . . .
H4 H 0.924923 0.268645 0.486522 0.044 Uiso 1 1 calc R . . . .
C5 C 0.8644(3) 0.39253(18) 0.5003(2) 0.0339(6) Uani 1 1 d . . . . .
H5 H 0.899949 0.411698 0.434752 0.041 Uiso 1 1 calc R . . . .
C6 C 0.7985(3) 0.44959(16) 0.5670(2) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.789408 0.507994 0.546438 0.034 Uiso 1 1 calc R . . . .
C7 C 0.6971(3) 0.30091(18) 0.7925(2) 0.0399(7) Uani 1 1 d . . . . .
H7A H 0.741750 0.333472 0.857638 0.060 Uiso 1 1 calc GR . . . .
H7B H 0.727233 0.240863 0.802134 0.060 Uiso 1 1 calc GR . . . .
H7C H 0.584251 0.305481 0.783449 0.060 Uiso 1 1 calc GR . . . .
C8 C 0.4792(3) 0.48465(15) 0.75884(19) 0.0238(5) Uani 1 1 d . . . . .
C9 C 0.4005(3) 0.52918(16) 0.8333(2) 0.0293(6) Uani 1 1 d . . . . .
C10 C 0.2436(3) 0.51322(18) 0.8310(2) 0.0356(6) Uani 1 1 d . . . . .
H10 H 0.189080 0.542056 0.881776 0.043 Uiso 1 1 calc R . . . .
C11 C 0.1654(3) 0.45687(18) 0.7572(2) 0.0379(7) Uani 1 1 d . . . . .
H11 H 0.058238 0.447206 0.757804 0.045 Uiso 1 1 calc R . . . .
C12 C 0.2417(3) 0.41427(18) 0.6824(2) 0.0341(6) Uani 1 1 d . . . . .
H12 H 0.187345 0.375888 0.630791 0.041 Uiso 1 1 calc R . . . .
C13 C 0.3985(3) 0.42808(16) 0.6833(2) 0.0277(5) Uani 1 1 d . . . . .
H13 H 0.451711 0.398783 0.632150 0.033 Uiso 1 1 calc R . . . .
C14 C 0.4803(3) 0.59308(17) 0.9129(2) 0.0379(7) Uani 1 1 d . . . . .
H14A H 0.570854 0.566569 0.956026 0.057 Uiso 1 1 calc GR . . . .
H14B H 0.409034 0.612535 0.962660 0.057 Uiso 1 1 calc GR . . . .
H14C H 0.513227 0.641918 0.871997 0.057 Uiso 1 1 calc GR . . . .
C15 C 0.6962(3) 0.60287(15) 0.69164(19) 0.0231(5) Uani 1 1 d . . . . .
C16 C 0.8282(3) 0.65249(16) 0.7197(2) 0.0288(6) Uani 1 1 d . . . . .
H16 H 0.908528 0.633240 0.774566 0.035 Uiso 1 1 calc R . . . .
C17 C 0.8419(3) 0.72996(16) 0.6675(2) 0.0327(6) Uani 1 1 d . . . . .
H17 H 0.931847 0.763738 0.686918 0.039 Uiso 1 1 calc R . . . .
C18 C 0.7266(3) 0.75841(16) 0.5876(2) 0.0330(6) Uani 1 1 d . . . . .
H18 H 0.737764 0.811115 0.551298 0.040 Uiso 1 1 calc R . . . .
C19 C 0.5941(3) 0.71012(16) 0.5603(2) 0.0313(6) Uani 1 1 d . . . . .
H19 H 0.513652 0.730232 0.506126 0.038 Uiso 1 1 calc R . . . .
C20 C 0.5784(3) 0.63246(16) 0.6119(2) 0.0278(5) Uani 1 1 d . . . . .
H20 H 0.487482 0.599430 0.592947 0.033 Uiso 1 1 calc R . . . .
O1W O 1.0021(3) 0.39192(14) 0.9978(2) 0.0298(5) Uani 0.75 1 d . . P . .
H1WA H 0.945222 0.427837 0.955967 0.045 Uiso 0.75 1 d G . P . .
H1WB H 1.073334 0.423183 1.035135 0.045 Uiso 0.75 1 d G . P . .


_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 1.4888(17) . ?
P1 C1 1.810(2) . ?
P1 C8 1.804(2) . ?
P1 C15 1.798(2) . ?
C1 C2 1.410(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.392(4) . ?
C2 C7 1.493(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.403(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.391(4) . ?
C9 C14 1.499(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.394(3) . ?
C15 C20 1.395(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
O1W H1WA 0.8690 . ?
O1W H1WB 0.8695 . ?

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 C1 111.18(10) . . ?
O1 P1 C8 114.90(10) . . ?
O1 P1 C15 111.72(10) . . ?
C8 P1 C1 107.53(11) . . ?
C15 P1 C1 106.05(11) . . ?
C15 P1 C8 104.89(11) . . ?
C2 C1 P1 120.36(19) . . ?
C6 C1 P1 119.91(19) . . ?
C6 C1 C2 119.4(2) . . ?
C1 C2 C7 123.2(2) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 C7 118.9(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 121.03(18) . . ?
C13 C8 P1 119.11(19) . . ?
C13 C8 C9 119.8(2) . . ?
C8 C9 C14 121.9(2) . . ?
C10 C9 C8 118.0(2) . . ?
C10 C9 C14 120.1(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 119.35(18) . . ?
C16 C15 C20 119.4(2) . . ?
C20 C15 P1 121.24(18) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
H1WA O1W H1WB 104.6 . . ?

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 C1 C2 C3 -171.93(18) . . . . ?
P1 C1 C2 C7 8.0(3) . . . . ?
P1 C1 C6 C5 172.17(19) . . . . ?
P1 C8 C9 C10 -179.57(19) . . . . ?
P1 C8 C9 C14 1.1(3) . . . . ?
P1 C8 C13 C12 -179.82(19) . . . . ?
P1 C15 C16 C17 177.86(19) . . . . ?
P1 C15 C20 C19 -177.78(19) . . . . ?
O1 P1 C1 C2 55.6(2) . . . . ?
O1 P1 C1 C6 -118.17(19) . . . . ?
O1 P1 C8 C9 48.4(2) . . . . ?
O1 P1 C8 C13 -132.93(19) . . . . ?
O1 P1 C15 C16 25.5(2) . . . . ?
O1 P1 C15 C20 -155.85(19) . . . . ?
C1 P1 C8 C9 172.72(19) . . . . ?
C1 P1 C8 C13 -8.6(2) . . . . ?
C1 P1 C15 C16 -95.7(2) . . . . ?
C1 P1 C15 C20 82.9(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 C1 C2 C3 1.9(3) . . . . ?
C6 C1 C2 C7 -178.2(2) . . . . ?
C7 C2 C3 C4 179.7(2) . . . . ?
C8 P1 C1 C2 -71.0(2) . . . . ?
C8 P1 C1 C6 115.3(2) . . . . ?
C8 P1 C15 C16 150.6(2) . . . . ?
C8 P1 C15 C20 -30.8(2) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C13 C8 C9 C10 1.7(4) . . . . ?
C13 C8 C9 C14 -177.6(2) . . . . ?
C14 C9 C10 C11 178.2(2) . . . . ?
C15 P1 C1 C2 177.21(19) . . . . ?
C15 P1 C1 C6 3.5(2) . . . . ?
C15 P1 C8 C9 -74.7(2) . . . . ?
C15 P1 C8 C13 104.0(2) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C15 C20 C19 0.8(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C20 C15 C16 C17 -0.8(4) . . . . ?

_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_fe361
_database_code_depnum_ccdc_archive 'CCDC 1937469'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 O1 P1'
_chemical_formula_sum            'C21 H21 O P'
_chemical_formula_weight         320.35
_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'
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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   12.4223(6)
_cell_length_b                   12.4223(6)
_cell_length_c                   19.7979(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2645.8(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.503
_cell_measurement_theta_min      2.796
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.3923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1268 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.9113. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.259
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10958
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.796
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1215
_reflns_number_total             1354
_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 V8.38A (Bruker AXS, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         1354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.085
_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)+(0.0255P)²+5.0067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0890
_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:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.333333 0.666667 0.49796(3) 0.02108(16) Uani 1 3 d S T P . .
O1 O 0.333333 0.666667 0.42277(8) 0.0303(4) Uani 1 3 d S T P . .
C1 C 0.28602(12) 0.51581(12) 0.53377(6) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.21082(13) 0.47043(13) 0.59087(7) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.181520 0.519488 0.612114 0.027 Uiso 1 1 calc R . . . .
C3 C 0.17812(13) 0.35413(13) 0.61714(7) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.126384 0.324613 0.655963 0.029 Uiso 1 1 calc R . . . .
C4 C 0.22017(12) 0.28047(13) 0.58733(7) 0.0248(3) Uani 1 1 d . . . . .
C5 C 0.29482(14) 0.32599(14) 0.52995(8) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.323971 0.276784 0.508741 0.034 Uiso 1 1 calc R . . . .
C6 C 0.32744(13) 0.44163(14) 0.50319(7) 0.0268(3) Uani 1 1 d . . . . .
H6 H 0.378088 0.470479 0.463941 0.032 Uiso 1 1 calc R . . . .
C7 C 0.18679(15) 0.15454(15) 0.61483(9) 0.0373(4) Uani 1 1 d . . . . .
H7A H 0.262946 0.152745 0.625400 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.138606 0.090699 0.581027 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.137081 0.138202 0.655968 0.056 Uiso 1 1 calc GR . . . .


_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 1.4885(17) . ?
P1 C1 1.8051(14) 2_665 ?
P1 C1 1.8051(14) . ?
P1 C1 1.8051(14) 3_565 ?
C1 C2 1.3935(18) . ?
C1 C6 1.3980(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3916(19) . ?
C4 C5 1.395(2) . ?
C4 C7 1.506(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 C1 113.13(4) . 3_565 ?
O1 P1 C1 113.13(4) . 2_665 ?
O1 P1 C1 113.13(4) . . ?
C1 P1 C1 105.58(5) 3_565 2_665 ?
C1 P1 C1 105.58(5) 2_665 . ?
C1 P1 C1 105.58(5) 3_565 . ?
C2 C1 P1 122.89(10) . . ?
C2 C1 C6 118.55(13) . . ?
C6 C1 P1 118.56(10) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.79(13) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.90(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 118.09(13) . . ?
C3 C4 C7 122.07(13) . . ?
C5 C4 C7 119.84(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.42(13) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.24(13) . . ?
C5 C6 H6 119.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 C1 C2 C3 -179.15(10) . . . . ?
P1 C1 C6 C5 178.86(11) . . . . ?
O1 P1 C1 C2 -140.75(10) . . . . ?
O1 P1 C1 C6 39.77(12) . . . . ?
C1 P1 C1 C2 -16.52(13) 3_565 . . . ?
C1 P1 C1 C2 95.03(9) 2_665 . . . ?
C1 P1 C1 C6 164.00(11) 3_565 . . . ?
C1 P1 C1 C6 -84.45(15) 2_665 . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C4 C7 179.71(13) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C7 C4 C5 C6 179.98(14) . . . . ?

_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_ffe313
_database_code_depnum_ccdc_archive 'CCDC 1898475'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2018-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H21 O P), H2 O2'
_chemical_formula_sum            'C42 H44 O4 P2'
_chemical_formula_weight         674.71
_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 0.0033 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'
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                   15.5361(11)
_cell_length_b                   12.2423(9)
_cell_length_c                   19.5371(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.688(2)
_cell_angle_gamma                90
_cell_volume                     3594.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.406
_cell_measurement_theta_min      2.241
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1799 before and 0.1072 after correction. The Ratio of minimum to maximum transmission is 0.6465. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.372
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.146
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2615
_reflns_number_total             3170
_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 V8.38A (Bruker AXS, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.084
_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)+(0.0544P)²+12.7266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.40328(5) 0.25641(6) 0.40678(4) 0.0159(2) Uani 1 1 d . . . . .
O1 O 0.46984(13) 0.26255(16) 0.36347(10) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.34300(18) 0.3824(2) 0.40679(13) 0.0160(6) Uani 1 1 d . . . . .
C2 C 0.39073(19) 0.4790(2) 0.42346(15) 0.0204(6) Uani 1 1 d . . . . .
H2 H 0.453842 0.477355 0.433596 0.024 Uiso 1 1 calc R . . . .
C3 C 0.3479(2) 0.5771(2) 0.42551(15) 0.0222(7) Uani 1 1 d . . . . .
H3 H 0.381807 0.642010 0.437711 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2551(2) 0.5821(2) 0.40983(15) 0.0212(6) Uani 1 1 d . . . . .
C5 C 0.20730(19) 0.4856(2) 0.39222(15) 0.0221(7) Uani 1 1 d . . . . .
H5 H 0.144139 0.487714 0.380889 0.027 Uiso 1 1 calc R . . . .
C6 C 0.24995(19) 0.3867(2) 0.39087(15) 0.0190(6) Uani 1 1 d . . . . .
H6 H 0.216072 0.321689 0.379133 0.023 Uiso 1 1 calc R . . . .
C7 C 0.2082(2) 0.6897(3) 0.4106(2) 0.0378(9) Uani 1 1 d . . . . .
H7A H 0.185406 0.693981 0.452865 0.057 Uiso 1 1 calc GR . . . .
H7B H 0.158645 0.695510 0.368191 0.057 Uiso 1 1 calc GR . . . .
H7C H 0.250213 0.749656 0.411092 0.057 Uiso 1 1 calc GR . . . .
C8 C 0.45521(18) 0.2270(2) 0.49813(15) 0.0169(6) Uani 1 1 d . . . . .
C9 C 0.43589(18) 0.2839(2) 0.55394(15) 0.0193(6) Uani 1 1 d . . . . .
H9 H 0.391085 0.338626 0.544489 0.023 Uiso 1 1 calc R . . . .
C10 C 0.4813(2) 0.2617(2) 0.62318(15) 0.0221(7) Uani 1 1 d . . . . .
H10 H 0.467537 0.302217 0.660509 0.027 Uiso 1 1 calc R . . . .
C11 C 0.54634(19) 0.1815(2) 0.63916(15) 0.0209(6) Uani 1 1 d . . . . .
C12 C 0.56397(19) 0.1235(2) 0.58319(16) 0.0229(7) Uani 1 1 d . . . . .
H12 H 0.607361 0.067068 0.592913 0.027 Uiso 1 1 calc R . . . .
C13 C 0.52016(19) 0.1454(2) 0.51381(16) 0.0220(7) Uani 1 1 d . . . . .
H13 H 0.534231 0.104994 0.476586 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5976(2) 0.1578(3) 0.71406(16) 0.0324(8) Uani 1 1 d . . . . .
H14A H 0.587010 0.216219 0.745269 0.049 Uiso 1 1 calc GR . . . .
H14B H 0.661250 0.153867 0.716398 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.577770 0.087966 0.729245 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.32062(17) 0.1524(2) 0.37587(14) 0.0161(6) Uani 1 1 d . . . . .
C16 C 0.27784(18) 0.0985(2) 0.42065(15) 0.0171(6) Uani 1 1 d . . . . .
H16 H 0.293563 0.114178 0.469879 0.021 Uiso 1 1 calc R . . . .
C17 C 0.21232(18) 0.0220(2) 0.39353(15) 0.0199(6) Uani 1 1 d . . . . .
H17 H 0.183832 -0.014677 0.424628 0.024 Uiso 1 1 calc R . . . .
C18 C 0.18750(19) -0.0022(2) 0.32164(16) 0.0226(7) Uani 1 1 d . . . . .
C19 C 0.2317(2) 0.0517(3) 0.27737(16) 0.0245(7) Uani 1 1 d . . . . .
H19 H 0.216176 0.035820 0.228165 0.029 Uiso 1 1 calc R . . . .
C20 C 0.29724(19) 0.1273(2) 0.30387(15) 0.0206(6) Uani 1 1 d . . . . .
H20 H 0.326706 0.162707 0.272939 0.025 Uiso 1 1 calc R . . . .
C21 C 0.1176(3) -0.0853(3) 0.2913(2) 0.0456(10) Uani 1 1 d . . . . .
H21A H 0.146158 -0.153135 0.281954 0.068 Uiso 1 1 calc GR . . . .
H21B H 0.079158 -0.057494 0.246954 0.068 Uiso 1 1 calc GR . . . .
H21C H 0.081859 -0.099617 0.325014 0.068 Uiso 1 1 calc GR . . . .
O2 O 0.53102(16) 0.1151(2) 0.28261(13) 0.0431(6) Uani 1 1 d . . . A 1
H2A H 0.505515 0.142508 0.313019 0.052 Uiso 1 1 d R . . A 1


_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 1.495(2) . ?
P1 C1 1.805(3) . ?
P1 C8 1.799(3) . ?
P1 C15 1.801(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.400(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(4) . ?
C4 C5 1.390(4) . ?
C4 C7 1.507(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.390(4) . ?
C8 C13 1.397(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 C12 1.389(4) . ?
C11 C14 1.506(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.392(4) . ?
C15 C20 1.395(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(4) . ?
C18 C19 1.398(4) . ?
C18 C21 1.496(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 O2 1.389(5) 2_655 ?
O2 H2A 0.8611 . ?

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 C1 112.99(12) . . ?
O1 P1 C8 111.78(12) . . ?
O1 P1 C15 112.49(12) . . ?
C8 P1 C1 105.87(12) . . ?
C8 P1 C15 107.05(13) . . ?
C15 P1 C1 106.18(12) . . ?
C2 C1 P1 118.7(2) . . ?
C2 C1 C6 118.7(3) . . ?
C6 C1 P1 122.6(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C7 120.6(3) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C7 121.1(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 P1 123.1(2) . . ?
C9 C8 C13 118.3(3) . . ?
C13 C8 P1 118.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 117.6(3) . . ?
C10 C11 C14 122.1(3) . . ?
C12 C11 C14 120.4(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 P1 122.6(2) . . ?
C16 C15 C20 119.1(2) . . ?
C20 C15 P1 118.3(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 118.1(3) . . ?
C17 C18 C21 122.2(3) . . ?
C19 C18 C21 119.7(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 O2 H2A 107.4 2_655 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A O1 0.86 1.93 2.724(3) 153.1 . yes

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 C1 C2 C3 -178.8(2) . . . . ?
P1 C1 C6 C5 179.5(2) . . . . ?
P1 C8 C9 C10 -176.5(2) . . . . ?
P1 C8 C13 C12 177.5(2) . . . . ?
P1 C15 C16 C17 177.6(2) . . . . ?
P1 C15 C20 C19 -177.2(2) . . . . ?
O1 P1 C1 C2 -51.5(2) . . . . ?
O1 P1 C1 C6 128.7(2) . . . . ?
O1 P1 C8 C9 133.4(2) . . . . ?
O1 P1 C8 C13 -44.4(3) . . . . ?
O1 P1 C15 C16 151.3(2) . . . . ?
O1 P1 C15 C20 -30.5(3) . . . . ?
C1 P1 C8 C9 10.0(3) . . . . ?
C1 P1 C8 C13 -167.9(2) . . . . ?
C1 P1 C15 C16 -84.7(2) . . . . ?
C1 P1 C15 C20 93.6(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C7 -178.7(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C7 C4 C5 C6 179.4(3) . . . . ?
C8 P1 C1 C2 71.2(2) . . . . ?
C8 P1 C1 C6 -108.6(2) . . . . ?
C8 P1 C15 C16 28.1(3) . . . . ?
C8 P1 C15 C20 -153.6(2) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C9 C10 C11 C14 178.8(3) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C8 -0.9(5) . . . . ?
C13 C8 C9 C10 1.3(4) . . . . ?
C14 C11 C12 C13 -178.0(3) . . . . ?
C15 P1 C1 C2 -175.2(2) . . . . ?
C15 P1 C1 C6 5.0(3) . . . . ?
C15 P1 C8 C9 -103.0(2) . . . . ?
C15 P1 C8 C13 79.2(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C15 C20 C19 1.1(4) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
C16 C17 C18 C21 179.4(3) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C18 C19 C20 C15 -0.4(5) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
C21 C18 C19 C20 -179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
