# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_ga214
_database_code_depnum_ccdc_archive 'CCDC 1449057'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-10-22 downloaded from the CCDC.
;
_audit_creation_date             2016-01-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H24 O2 P2, C8 H18 O6'
_chemical_formula_sum            'C34 H42 O8 P2'
_chemical_formula_weight         640.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.6352(2)
_cell_length_b                   9.0229(2)
_cell_length_c                   11.5477(3)
_cell_angle_alpha                85.762(2)
_cell_angle_beta                 81.565(2)
_cell_angle_gamma                67.8510(10)
_cell_volume                     824.16(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8640
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      70.155
_cell_measurement_theta_min      3.870
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.690
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1064 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.8584.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.045
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19043
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.148
_diffrn_reflns_theta_min         3.870
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_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                2453
_reflns_number_total             3099
_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       'APEX 3 (Bruker-AXS, Madison WI)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.080
_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)+(0.0234P)²+1.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C14, C14A}
3. Restrained distances
 C15A-C14A \\sim C15-C14
 with sigma of 0.01
 C16-C15 \\sim C16A-C15A
 with sigma of 0.01
 C15A-C14A \\sim C17A-C14A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C14A \\sim C14 \\sim C15 \\sim C17A \\sim C16 \\sim C15A \\sim C17 \\sim C16A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14A) = Uanis(C14)
5. Rigid body (RIGU) restrains
 C14A, C14, C15, C17A, C16, C15A, C17, C16A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(C14A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C14)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
7.a Riding coordinates:
 O4(H4)
7.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C15A(H15C,H15D)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13)
7.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C16A(H16D,H16E,H16F), C17A(H17D,
 H17E,H17F)
;
_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 0.79732(7) 0.23494(7) 0.53840(6) 0.01984(17) Uani 1 1 d . . . . .
O1 O 0.7265(2) 0.2818(2) 0.42453(15) 0.0251(4) Uani 1 1 d . . . . .
C1 C 1.0029(3) 0.0757(3) 0.5248(2) 0.0213(5) Uani 1 1 d . . . . .
H1A H 1.0839 0.1118 0.4723 0.026 Uiso 1 1 calc R . . . .
H1B H 1.0428 0.0501 0.6026 0.026 Uiso 1 1 calc R . . . .
C2 C 0.8167(3) 0.3988(3) 0.6075(2) 0.0214(5) Uani 1 1 d . . . . .
C3 C 0.9680(4) 0.4023(3) 0.6303(3) 0.0401(8) Uani 1 1 d . . . . .
H3 H 1.0698 0.3138 0.6101 0.048 Uiso 1 1 calc R . . . .
C4 C 0.9722(4) 0.5344(4) 0.6824(3) 0.0449(9) Uani 1 1 d . . . . .
H4A H 1.0765 0.5359 0.6982 0.054 Uiso 1 1 calc R . . . .
C5 C 0.8247(4) 0.6633(3) 0.7110(3) 0.0363(7) Uani 1 1 d . . . . .
H5 H 0.8271 0.7539 0.7466 0.044 Uiso 1 1 calc R . . . .
C6 C 0.6736(4) 0.6605(3) 0.6879(3) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.5721 0.7495 0.7076 0.041 Uiso 1 1 calc R . . . .
C7 C 0.6686(3) 0.5291(3) 0.6363(2) 0.0280(6) Uani 1 1 d . . . . .
H7 H 0.5642 0.5280 0.6205 0.034 Uiso 1 1 calc R . . . .
C8 C 0.6621(3) 0.1654(3) 0.6429(2) 0.0206(5) Uani 1 1 d . . . . .
C9 C 0.6952(3) 0.1270(3) 0.7582(2) 0.0266(6) Uani 1 1 d . . . . .
H9 H 0.7921 0.1350 0.7825 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5871(4) 0.0771(3) 0.8372(2) 0.0308(6) Uani 1 1 d . . . . .
H10 H 0.6090 0.0524 0.9160 0.037 Uiso 1 1 calc R . . . .
C11 C 0.4466(3) 0.0631(3) 0.8016(2) 0.0300(6) Uani 1 1 d . . . . .
H11 H 0.3726 0.0286 0.8559 0.036 Uiso 1 1 calc R . . . .
C12 C 0.4145(3) 0.0995(3) 0.6873(2) 0.0291(6) Uani 1 1 d . . . . .
H12 H 0.3187 0.0891 0.6630 0.035 Uiso 1 1 calc R . . . .
C13 C 0.5211(3) 0.1513(3) 0.6076(2) 0.0263(6) Uani 1 1 d . . . . .
H13 H 0.4978 0.1771 0.5292 0.032 Uiso 1 1 calc R . . . .
O2 O 0.9118(2) 0.0580(2) 0.00183(17) 0.0311(5) Uani 1 1 d . . . . .
O3 O 0.9431(2) 0.1622(2) 0.17189(15) 0.0264(4) Uani 1 1 d . . . . .
O4 O 0.8162(2) 0.1062(2) 0.23679(17) 0.0341(5) Uani 1 1 d . . . . .
H4 H 0.7842 0.1719 0.2926 0.041 Uiso 1 1 d R . . . .
C14 C 0.9046(3) 0.1979(3) 0.0558(2) 0.0277(6) Uani 0.855(6) 1 d D U P A 1
C15 C 0.7265(5) 0.3166(7) 0.0432(5) 0.0337(14) Uani 0.855(6) 1 d D U P A 1
H15A H 0.7188 0.3468 -0.0406 0.040 Uiso 0.855(6) 1 calc R . P A 1
H15B H 0.6455 0.2635 0.0693 0.040 Uiso 0.855(6) 1 calc R . P A 1
C16 C 0.6764(4) 0.4666(4) 0.1126(3) 0.0372(10) Uani 0.855(6) 1 d D U P A 1
H16A H 0.7485 0.5260 0.0818 0.056 Uiso 0.855(6) 1 calc GR . P A 1
H16B H 0.6897 0.4376 0.1950 0.056 Uiso 0.855(6) 1 calc GR . P A 1
H16C H 0.5584 0.5337 0.1060 0.056 Uiso 0.855(6) 1 calc GR . P A 1
C17 C 1.0382(14) 0.2596(18) -0.0047(5) 0.0406(14) Uani 0.855(6) 1 d . U P A 1
H17A H 1.1495 0.1874 0.0136 0.061 Uiso 0.855(6) 1 calc GR . P A 1
H17B H 1.0145 0.3670 0.0229 0.061 Uiso 0.855(6) 1 calc GR . P A 1
H17C H 1.0364 0.2640 -0.0896 0.061 Uiso 0.855(6) 1 calc GR . P A 1
C14A C 0.9046(3) 0.1979(3) 0.0558(2) 0.0277(6) Uani 0.145(6) 1 d D U P A 2
C15A C 1.042(8) 0.265(10) 0.014(3) 0.030(4) Uani 0.145(6) 1 d D U P A 2
H15C H 1.0250 0.3623 0.0567 0.036 Uiso 0.145(6) 1 calc R . P A 2
H15D H 1.1563 0.1841 0.0220 0.036 Uiso 0.145(6) 1 calc R . P A 2
C16A C 1.013(2) 0.301(2) -0.1121(18) 0.034(5) Uani 0.145(6) 1 d D U P A 2
H16D H 1.0903 0.3512 -0.1512 0.051 Uiso 0.145(6) 1 calc GR . P A 2
H16E H 0.8965 0.3740 -0.1159 0.051 Uiso 0.145(6) 1 calc GR . P A 2
H16F H 1.0340 0.2013 -0.1513 0.051 Uiso 0.145(6) 1 calc GR . P A 2
C17A C 0.7140(16) 0.291(5) 0.070(4) 0.034(6) Uani 0.145(6) 1 d D U P A 2
H17D H 0.6743 0.3102 -0.0070 0.051 Uiso 0.145(6) 1 calc GR . P A 2
H17E H 0.6885 0.3944 0.1060 0.051 Uiso 0.145(6) 1 calc GR . P A 2
H17F H 0.6572 0.2298 0.1200 0.051 Uiso 0.145(6) 1 calc GR . 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 1.4967(18) . ?
P1 C1 1.808(2) . ?
P1 C2 1.803(2) . ?
P1 C8 1.800(3) . ?
C1 C1 1.540(4) 2_756 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.382(4) . ?
C2 C7 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(4) . ?
C8 C13 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
O2 O2 1.484(3) 2_755 ?
O2 C14 1.425(3) . ?
O3 O4 1.462(2) . ?
O3 C14 1.413(3) . ?
O4 H4 0.8501 . ?
C14 C15 1.528(4) . ?
C14 C17 1.522(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.510(13) . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 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 113.18(11) . . ?
O1 P1 C2 113.23(11) . . ?
O1 P1 C8 110.95(11) . . ?
C2 P1 C1 106.97(11) . . ?
C8 P1 C1 106.58(12) . . ?
C8 P1 C2 105.41(11) . . ?
P1 C1 H1A 109.4 . . ?
P1 C1 H1B 109.4 . . ?
C1 C1 P1 111.2(2) 2_756 . ?
C1 C1 H1A 109.4 2_756 . ?
C1 C1 H1B 109.4 2_756 . ?
H1A C1 H1B 108.0 . . ?
C3 C2 P1 124.06(19) . . ?
C3 C2 C7 119.5(2) . . ?
C7 C2 P1 116.42(19) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C9 C8 P1 121.35(19) . . ?
C13 C8 P1 119.1(2) . . ?
C13 C8 C9 119.6(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 O2 O2 106.6(2) . 2_755 ?
C14 O3 O4 107.64(18) . . ?
O3 O4 H4 97.8 . . ?
O2 C14 C15 103.2(3) . . ?
O2 C14 C17 111.7(5) . . ?
O3 C14 O2 110.4(2) . . ?
O3 C14 C15 115.5(3) . . ?
O3 C14 C17 104.5(3) . . ?
C17 C14 C15 111.7(6) . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.4(4) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H15C C15A H15D 109.6 . . ?
C16A C15A H15C 111.9 . . ?
C16A C15A H15D 111.9 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 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 C2 C3 C4 179.0(3) . . . . ?
P1 C2 C7 C6 -179.0(2) . . . . ?
P1 C8 C9 C10 178.62(19) . . . . ?
P1 C8 C13 C12 -179.32(19) . . . . ?
O1 P1 C1 C1 -59.0(3) . . . 2_756 ?
O1 P1 C2 C3 -118.2(3) . . . . ?
O1 P1 C2 C7 60.4(2) . . . . ?
O1 P1 C8 C9 -174.93(18) . . . . ?
O1 P1 C8 C13 4.5(2) . . . . ?
C1 P1 C2 C3 7.2(3) . . . . ?
C1 P1 C2 C7 -174.3(2) . . . . ?
C1 P1 C8 C9 61.4(2) . . . . ?
C1 P1 C8 C13 -119.11(19) . . . . ?
C2 P1 C1 C1 175.6(2) . . . 2_756 ?
C2 P1 C8 C9 -52.0(2) . . . . ?
C2 P1 C8 C13 127.44(19) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
C8 P1 C1 C1 63.2(3) . . . 2_756 ?
C8 P1 C2 C3 120.4(3) . . . . ?
C8 P1 C2 C7 -61.1(2) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C13 C8 C9 C10 -0.8(4) . . . . ?
O2 O2 C14 O3 -62.3(3) 2_755 . . . ?
O2 O2 C14 C15 173.7(3) 2_755 . . . ?
O2 O2 C14 C17 53.5(5) 2_755 . . . ?
O2 C14 C15 C16 169.9(3) . . . . ?
O3 C14 C15 C16 49.4(5) . . . . ?
O4 O3 C14 O2 -61.3(2) . . . . ?
O4 O3 C14 C15 55.2(4) . . . . ?
O4 O3 C14 C17 178.4(6) . . . . ?
C17 C14 C15 C16 -69.9(6) . . . . ?

_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_ffe021a
_database_code_depnum_ccdc_archive 'CCDC 1945941'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-10-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-05
_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         'C26 H48 O2 P2, H2 O2'
_chemical_formula_sum            'C26 H50 O4 P2'
_chemical_formula_weight         488.60
_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                   24.4329(13)
_cell_length_b                   11.0268(6)
_cell_length_c                   10.9841(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.110(2)
_cell_angle_gamma                90
_cell_volume                     2701.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      2.619
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7431
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1490 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.9287.
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    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.619
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                2528
_reflns_number_total             3109
_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       'APEX 3 (Bruker-AXS, Madison WI)'
_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         0.427
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.049
_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)+(0.0381P)²+4.6328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O2(H2A)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
;
_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 0.40896(2) 0.58440(4) 0.41146(4) 0.01114(12) Uani 1 1 d . . . . .
O1 O 0.40273(5) 0.58417(11) 0.26974(11) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.48406(7) 0.54305(15) 0.52975(16) 0.0140(3) Uani 1 1 d . . . . .
H1A H 0.5083 0.6177 0.5610 0.017 Uiso 1 1 calc R . . . .
H1B H 0.4814 0.5038 0.6082 0.017 Uiso 1 1 calc R . . . .
C2 C 0.35729(7) 0.47966(14) 0.43775(16) 0.0124(3) Uani 1 1 d . . . . .
H2 H 0.3658 0.4806 0.5349 0.015 Uiso 1 1 calc R . . . .
C3 C 0.36686(8) 0.34951(15) 0.40030(18) 0.0168(4) Uani 1 1 d . . . . .
H3A H 0.3612 0.3474 0.3058 0.020 Uiso 1 1 calc R . . . .
H3B H 0.4085 0.3239 0.4560 0.020 Uiso 1 1 calc R . . . .
C4 C 0.32311(8) 0.26122(15) 0.42057(19) 0.0192(4) Uani 1 1 d . . . . .
H4A H 0.3291 0.1791 0.3916 0.023 Uiso 1 1 calc R . . . .
H4B H 0.3314 0.2573 0.5165 0.023 Uiso 1 1 calc R . . . .
C5 C 0.25849(8) 0.30064(16) 0.34150(18) 0.0196(4) Uani 1 1 d . . . . .
H5A H 0.2312 0.2439 0.3591 0.024 Uiso 1 1 calc R . . . .
H5B H 0.2491 0.2977 0.2449 0.024 Uiso 1 1 calc R . . . .
C6 C 0.24842(8) 0.42871(16) 0.37982(19) 0.0203(4) Uani 1 1 d . . . . .
H6A H 0.2542 0.4298 0.4744 0.024 Uiso 1 1 calc R . . . .
H6B H 0.2066 0.4537 0.3246 0.024 Uiso 1 1 calc R . . . .
C7 C 0.29168(7) 0.51852(15) 0.35980(18) 0.0178(4) Uani 1 1 d . . . . .
H7A H 0.2856 0.6000 0.3901 0.021 Uiso 1 1 calc R . . . .
H7B H 0.2830 0.5238 0.2637 0.021 Uiso 1 1 calc R . . . .
C8 C 0.39384(7) 0.73297(15) 0.46225(17) 0.0138(3) Uani 1 1 d . . . . .
H8 H 0.3519 0.7535 0.3995 0.017 Uiso 1 1 calc R . . . .
C9 C 0.43329(10) 0.83338(17) 0.4452(2) 0.0319(5) Uani 1 1 d . . . . .
H9A H 0.4310 0.8317 0.3532 0.038 Uiso 1 1 calc R . . . .
H9B H 0.4755 0.8197 0.5076 0.038 Uiso 1 1 calc R . . . .
C10 C 0.41239(10) 0.95722(17) 0.4730(2) 0.0298(5) Uani 1 1 d . . . . .
H10A H 0.4397 1.0208 0.4665 0.036 Uiso 1 1 calc R . . . .
H10B H 0.3717 0.9741 0.4042 0.036 Uiso 1 1 calc R . . . .
C11 C 0.41118(10) 0.96282(18) 0.6096(2) 0.0323(5) Uani 1 1 d . . . . .
H11A H 0.3947 1.0419 0.6209 0.039 Uiso 1 1 calc R . . . .
H11B H 0.4526 0.9560 0.6791 0.039 Uiso 1 1 calc R . . . .
C12 C 0.37288(14) 0.86063(19) 0.6266(3) 0.0461(7) Uani 1 1 d . . . . .
H12A H 0.3306 0.8729 0.5638 0.055 Uiso 1 1 calc R . . . .
H12B H 0.3748 0.8626 0.7184 0.055 Uiso 1 1 calc R . . . .
C13 C 0.39434(12) 0.73664(18) 0.6007(2) 0.0368(6) Uani 1 1 d . . . . .
H13A H 0.4355 0.7211 0.6681 0.044 Uiso 1 1 calc R . . . .
H13B H 0.3678 0.6723 0.6089 0.044 Uiso 1 1 calc R . . . .
O2 O 0.47251(6) 0.72294(12) 0.18779(12) 0.0236(3) Uani 1 1 d . . . . .
H2A H 0.4492 0.6757 0.2215 0.035 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 1.5009(12) . ?
P1 C1 1.8208(16) . ?
P1 C2 1.8191(16) . ?
P1 C8 1.8166(16) . ?
C1 C1 1.533(3) 5_666 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2 1.0000 . ?
C2 C3 1.537(2) . ?
C2 C7 1.538(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.528(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.522(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.522(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C9 1.529(2) . ?
C8 C13 1.516(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.532(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.514(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.532(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O2 O2 1.474(2) 2_655 ?
O2 H2A 0.9513 . ?

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 112.67(7) . . ?
O1 P1 C2 112.37(7) . . ?
O1 P1 C8 111.89(7) . . ?
C2 P1 C1 106.86(8) . . ?
C8 P1 C1 106.18(8) . . ?
C8 P1 C2 106.41(7) . . ?
P1 C1 H1A 109.0 . . ?
P1 C1 H1B 109.0 . . ?
C1 C1 P1 112.96(15) 5_666 . ?
C1 C1 H1A 109.0 5_666 . ?
C1 C1 H1B 109.0 5_666 . ?
H1A C1 H1B 107.8 . . ?
P1 C2 H2 107.9 . . ?
C3 C2 P1 111.04(11) . . ?
C3 C2 H2 107.9 . . ?
C3 C2 C7 110.44(13) . . ?
C7 C2 P1 111.58(11) . . ?
C7 C2 H2 107.9 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.34(13) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.06(14) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.76(14) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.22(14) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C2 C7 H7A 109.4 . . ?
C2 C7 H7B 109.4 . . ?
C6 C7 C2 111.36(14) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
P1 C8 H8 105.8 . . ?
C9 C8 P1 113.46(12) . . ?
C9 C8 H8 105.8 . . ?
C13 C8 P1 114.38(12) . . ?
C13 C8 H8 105.8 . . ?
C13 C8 C9 110.87(16) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C8 C9 C10 110.07(16) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 112.14(17) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 C12 110.66(17) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 111.28(19) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C8 C13 C12 110.31(17) . . ?
C8 C13 H13A 109.6 . . ?
C8 C13 H13B 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O2 O2 H2A 95.9 2_655 . ?

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 C2 C3 C4 -179.33(12) . . . . ?
P1 C2 C7 C6 178.75(12) . . . . ?
P1 C8 C9 C10 172.78(14) . . . . ?
P1 C8 C13 C12 -172.33(17) . . . . ?
O1 P1 C1 C1 -29.49(19) . . . 5_666 ?
O1 P1 C2 C3 58.28(13) . . . . ?
O1 P1 C2 C7 -65.39(13) . . . . ?
O1 P1 C8 C9 -56.30(16) . . . . ?
O1 P1 C8 C13 175.16(14) . . . . ?
C1 P1 C2 C3 -65.80(13) . . . . ?
C1 P1 C2 C7 170.53(11) . . . . ?
C1 P1 C8 C9 67.01(16) . . . . ?
C1 P1 C8 C13 -61.53(16) . . . . ?
C2 P1 C1 C1 94.40(17) . . . 5_666 ?
C2 P1 C8 C9 -179.39(14) . . . . ?
C2 P1 C8 C13 52.07(16) . . . . ?
C2 C3 C4 C5 56.43(19) . . . . ?
C3 C2 C7 C6 54.73(19) . . . . ?
C3 C4 C5 C6 -56.9(2) . . . . ?
C4 C5 C6 C7 56.7(2) . . . . ?
C5 C6 C7 C2 -56.0(2) . . . . ?
C7 C2 C3 C4 -55.00(19) . . . . ?
C8 P1 C1 C1 -152.31(16) . . . 5_666 ?
C8 P1 C2 C3 -178.93(11) . . . . ?
C8 P1 C2 C7 57.39(13) . . . . ?
C8 C9 C10 C11 55.8(2) . . . . ?
C9 C8 C13 C12 57.8(2) . . . . ?
C9 C10 C11 C12 -55.1(2) . . . . ?
C10 C11 C12 C13 55.4(3) . . . . ?
C11 C12 C13 C8 -57.0(3) . . . . ?
C13 C8 C9 C10 -56.9(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_ga229b
_database_code_depnum_ccdc_archive 'CCDC 1452863'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-10-22 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H10 O6'
_chemical_formula_sum            'C5 H10 O6'
_chemical_formula_weight         166.13
_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'

_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                   5.5661(6)
_cell_length_b                   15.4167(15)
_cell_length_c                   8.8545(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.306(3)
_cell_angle_gamma                90
_cell_volume                     759.20(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2704
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      27.487
_cell_measurement_theta_min      2.643
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1043 before and 0.0593 after correction.
 The Ratio of minimum to maximum transmission is 0.75.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0929 before and 0.0600 after correction.
 The Ratio of minimum to maximum transmission is 0.75.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 16324 reflections, Rint = 0.0627
 (9311 with I > 3sig(I), Rint = 0.0544)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.104
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2327
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.642
_diffrn_reflns_v_R_equivalents   ?
_diffrn_reflns_av_r_equivalents  0.0545
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_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                1859
_reflns_number_total             2327
_reflns_special_details          
;
 _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       'APEX 3 (Bruker-AXS, Madison WI)'
_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         0.183
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.036
_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)+(0.0467P)²+0.4994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.605(2) 0.395(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O4(H4), O6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_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
O1 O 0.9273(4) 0.70260(12) 0.47168(18) 0.0237(5) Uani 1 1 d . . . . .
O2 O 0.9219(4) 0.78901(12) 0.54533(18) 0.0232(5) Uani 1 1 d . . . . .
O3 O 0.6865(4) 0.64029(12) 0.65150(18) 0.0276(5) Uani 1 1 d . . . . .
O4 O 0.8418(4) 0.56453(12) 0.6749(2) 0.0324(5) Uani 1 1 d . . . . .
H4 H 0.9868 0.5858 0.7044 0.049 Uiso 1 1 d R . . . .
O5 O 0.6998(4) 0.85276(12) 0.34496(18) 0.0260(5) Uani 1 1 d . . . . .
O6 O 0.8545(4) 0.92970(12) 0.3421(2) 0.0328(5) Uani 1 1 d . . . . .
H6 H 0.9741 0.9045 0.2761 0.049 Uiso 1 1 d R . . . .
C1 C 0.6975(5) 0.66820(18) 0.4971(3) 0.0216(6) Uani 1 1 d . . . . .
C2 C 0.5265(5) 0.7449(2) 0.4873(3) 0.0283(6) Uani 1 1 d . . . . .
H2A H 0.4152 0.7445 0.5718 0.034 Uiso 1 1 calc R . . . .
H2B H 0.4315 0.7449 0.3903 0.034 Uiso 1 1 calc R . . . .
C3 C 0.6949(5) 0.82280(18) 0.4981(3) 0.0226(7) Uani 1 1 d . . . . .
C4 C 0.6541(6) 0.59503(19) 0.3858(3) 0.0295(7) Uani 1 1 d . . . . .
H4A H 0.6502 0.6182 0.2827 0.044 Uiso 1 1 calc GR . . . .
H4B H 0.5001 0.5671 0.4049 0.044 Uiso 1 1 calc GR . . . .
H4C H 0.7840 0.5524 0.3977 0.044 Uiso 1 1 calc GR . . . .
C5 C 0.6350(6) 0.8941(2) 0.6069(3) 0.0314(7) Uani 1 1 d . . . . .
H5A H 0.6272 0.8700 0.7090 0.047 Uiso 1 1 calc GR . . . .
H5B H 0.4792 0.9196 0.5765 0.047 Uiso 1 1 calc GR . . . .
H5C H 0.7597 0.9389 0.6058 0.047 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
O1 O2 1.484(2) . ?
O1 C1 1.411(3) . ?
O2 C3 1.414(3) . ?
O3 O4 1.463(3) . ?
O3 C1 1.437(3) . ?
O4 H4 0.8999 . ?
O5 O6 1.467(3) . ?
O5 C3 1.433(3) . ?
O6 H6 0.9837 . ?
C1 C2 1.519(4) . ?
C1 C4 1.511(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.524(4) . ?
C3 C5 1.508(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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
C1 O1 O2 103.45(19) . . ?
C3 O2 O1 103.55(18) . . ?
C1 O3 O4 109.04(18) . . ?
O3 O4 H4 105.5 . . ?
C3 O5 O6 108.08(17) . . ?
O5 O6 H6 95.9 . . ?
O1 C1 O3 109.8(2) . . ?
O1 C1 C2 105.6(2) . . ?
O1 C1 C4 107.4(2) . . ?
O3 C1 C2 103.7(2) . . ?
O3 C1 C4 112.7(2) . . ?
C4 C1 C2 117.4(2) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C1 C2 C3 103.1(2) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
O2 C3 O5 110.4(2) . . ?
O2 C3 C2 105.6(2) . . ?
O2 C3 C5 107.3(2) . . ?
O5 C3 C2 103.3(2) . . ?
O5 C3 C5 112.5(2) . . ?
C5 C3 C2 117.6(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O1 O2 C3 O5 -76.7(2) . . . . ?
O1 O2 C3 C2 34.2(2) . . . . ?
O1 O2 C3 C5 160.4(2) . . . . ?
O1 C1 C2 C3 -14.9(2) . . . . ?
O2 O1 C1 O3 -75.4(2) . . . . ?
O2 O1 C1 C2 35.8(2) . . . . ?
O2 O1 C1 C4 161.80(19) . . . . ?
O3 C1 C2 C3 100.5(2) . . . . ?
O4 O3 C1 O1 -68.8(2) . . . . ?
O4 O3 C1 C2 178.8(2) . . . . ?
O4 O3 C1 C4 50.8(3) . . . . ?
O6 O5 C3 O2 -68.7(2) . . . . ?
O6 O5 C3 C2 178.81(19) . . . . ?
O6 O5 C3 C5 51.1(3) . . . . ?
C1 O1 O2 C3 -44.58(19) . . . . ?
C1 C2 C3 O2 -12.7(2) . . . . ?
C1 C2 C3 O5 103.3(2) . . . . ?
C1 C2 C3 C5 -132.2(2) . . . . ?
C4 C1 C2 C3 -134.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.605(2)
2 0.395(2)

####################################################################### 
# 
# 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_temp
_database_code_depnum_ccdc_archive 'CCDC 1449061'
loop_
_audit_author_name
_audit_author_address
'Nattamai Bhuvanesh'
;Texas AM University
United States of America
;
_audit_update_record             
;
2019-10-14 deposited with the CCDC.	2019-10-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_temp                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data was collected using Bruker GADDS instrument. The
maximum two-theta angle could be collected is 121 degree due to
geometric constraints.
;
# end Validation Reply Form

_audit_creation_date             2015-12-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H10 O4'
_chemical_formula_sum            'C5 H10 O4'
_chemical_formula_weight         134.13
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.9845(4)
_cell_length_b                   8.9845(4)
_cell_length_c                   8.5007(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     686.19(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8034
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      60.511
_cell_measurement_theta_min      6.968
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  0.7388
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.8812.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.838
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.833
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         60.489
_diffrn_reflns_theta_min         6.970
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.838
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker GADDS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                491
_reflns_number_total             518
_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       'APEX 3 (Bruker-AXS, Madison WI)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(10)
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.195
_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)+(0.0189P)²+0.1611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0557
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.69906(16) 0.30842(15) 0.16390(17) 0.0366(5) Uani 1 1 d . . . . .
O2 O 0.63774(14) 0.05907(13) 0.13113(15) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.5746 0.0768 0.0607 0.034 Uiso 1 1 calc GR . . . .
C1 C 0.86845(19) 0.13155(19) 0.2500 0.0194(6) Uani 1 2 d S T P . .
H1A H 0.9710 0.1435 0.2093 0.023 Uiso 0.5 1 calc R . . . .
H1B H 0.8565 0.0290 0.2907 0.023 Uiso 0.5 1 calc R . . . .
C2 C 0.7539(2) 0.1647(2) 0.1222(2) 0.0219(5) Uani 1 1 d . . . . .
C3 C 0.8125(3) 0.1796(3) -0.0434(2) 0.0487(8) Uani 1 1 d . . . . .
H3A H 0.8519 0.0835 -0.0786 0.073 Uiso 1 1 calc GR . . . .
H3B H 0.8919 0.2543 -0.0457 0.073 Uiso 1 1 calc GR . . . .
H3C H 0.7316 0.2107 -0.1134 0.073 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
O1 O1 1.467(3) 8_665 ?
O1 C2 1.427(2) . ?
O2 H2 0.8400 . ?
O2 C2 1.413(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.525(2) . ?
C1 C2 1.525(2) 8_665 ?
C2 C3 1.509(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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
C2 O1 O1 102.84(11) . 8_665 ?
C2 O2 H2 109.5 . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 110.9 8_665 . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 8_665 . ?
C2 C1 H1B 110.9 . . ?
C2 C1 C2 104.1(2) . 8_665 ?
O1 C2 C1 103.48(15) . . ?
O1 C2 C3 105.78(17) . . ?
O2 C2 O1 109.84(15) . . ?
O2 C2 C1 109.20(13) . . ?
O2 C2 C3 111.53(18) . . ?
C3 C2 C1 116.52(15) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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
O1 O1 C2 O2 77.83(18) 8_665 . . . ?
O1 O1 C2 C1 -38.66(17) 8_665 . . . ?
O1 O1 C2 C3 -161.69(16) 8_665 . . . ?
C2 C1 C2 O1 14.93(8) 8_665 . . . ?
C2 C1 C2 O2 -102.01(15) 8_665 . . . ?
C2 C1 C2 C3 130.54(19) 8_665 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
