# 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.
#
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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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0234P)^2^+1.0293P] where P=(Fo^2^+2Fc^2^)/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
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0132(3) 0.0186(3) 0.0270(4) -0.0102(3) -0.0006(2) -0.0039(2)
O1 0.0200(9) 0.0272(10) 0.0277(10) -0.0080(8) -0.0017(7) -0.0074(7)
C1 0.0138(12) 0.0186(13) 0.0312(14) -0.0114(11) 0.0004(10) -0.0050(9)
C2 0.0206(13) 0.0196(13) 0.0246(14) -0.0083(10) -0.0004(10) -0.0078(10)
C3 0.0228(15) 0.0320(16) 0.065(2) -0.0232(15) -0.0091(13) -0.0046(12)
C4 0.0310(17) 0.0435(18) 0.069(2) -0.0219(17) -0.0120(15) -0.0182(14)
C5 0.0476(19) 0.0261(15) 0.0416(18) -0.0122(13) -0.0068(14) -0.0183(13)
C6 0.0347(16) 0.0218(14) 0.0422(18) -0.0115(12) -0.0042(13) -0.0044(11)
C7 0.0204(13) 0.0250(14) 0.0384(16) -0.0086(12) -0.0059(11) -0.0058(10)
C8 0.0160(12) 0.0144(12) 0.0294(14) -0.0098(10) 0.0007(10) -0.0030(9)
C9 0.0250(14) 0.0229(14) 0.0322(16) -0.0090(11) -0.0062(11) -0.0068(10)
C10 0.0387(16) 0.0286(15) 0.0252(15) -0.0081(12) -0.0026(12) -0.0118(12)
C11 0.0292(15) 0.0190(13) 0.0372(17) -0.0060(12) 0.0088(12) -0.0076(11)
C12 0.0188(13) 0.0280(14) 0.0411(17) -0.0020(12) -0.0056(11) -0.0086(11)
C13 0.0210(13) 0.0268(14) 0.0317(15) -0.0019(11) -0.0076(11) -0.0078(10)
O2 0.0287(11) 0.0243(10) 0.0359(11) -0.0122(8) -0.0128(8) 0.0003(8)
O3 0.0265(10) 0.0285(10) 0.0272(10) -0.0077(8) -0.0024(7) -0.0126(8)
O4 0.0418(12) 0.0380(11) 0.0303(11) -0.0108(9) 0.0033(9) -0.0246(9)
C14 0.0348(15) 0.0202(13) 0.0270(14) -0.0045(11) -0.0068(11) -0.0072(10)
C15 0.036(2) 0.025(3) 0.036(3) -0.004(2) -0.0132(16) -0.0032(16)
C16 0.0327(19) 0.0246(18) 0.049(2) -0.0099(16) -0.0059(15) -0.0024(14)
C17 0.045(2) 0.034(3) 0.040(3) 0.000(4) 0.003(3) -0.0141(18)
C14A 0.0348(15) 0.0202(13) 0.0270(14) -0.0045(11) -0.0068(11) -0.0072(10)
C15A 0.039(6) 0.020(6) 0.029(6) -0.003(6) -0.007(5) -0.008(5)
C16A 0.031(9) 0.025(9) 0.039(9) 0.002(7) 0.004(7) -0.006(7)
C17A 0.040(8) 0.020(9) 0.035(10) 0.008(8) -0.011(7) -0.002(7)
_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) . . . . ?
_shelx_res_file
;
TITL ga214_a.res in P-1
REM Old TITL GA214 in P-1 #2
REM SHELXT solution in P-1
REM R1 0.145, Rweak 0.012, Alpha 0.041, Orientation as input
REM Formula found by SHELXT: C17 O4 P
rem EXYZ C14 C14A
CELL 1.54178 8.6352 9.0229 11.5477 85.762 81.565 67.851
ZERR 1 0.0002 0.0002 0.0003 0.002 0.002 0.001
LATT 1
SFAC C H O P
UNIT 34 42 8 2
SADI 0.01 C15A C14A C15 C14
SADI 0.01 C16 C15 C16A C15A
SADI 0.01 C15A C14A C17A C14A
SIMU 0.01 0.02 2 C14A C14 C15 C17A C16 C15A C17 C16A
RIGU 0.01 0.01 C14A C14 C15 C17A C16 C15A C17 C16A
EADP C14A C14
EXYZ C14 C14A
L.S. 10
PLAN 20
SIZE 0.045 0.1 0.249
TEMP -173.14
acta
more -1
wpdb -1
htab
conf
BOND $H
fmap 2
REM
REM
REM
WGHT 0.023400 1.029300
FVAR 0.89177 0.85479
P1 4 0.797321 0.234936 0.538398 11.00000 0.01315 0.01856 =
0.02702 -0.01022 -0.00058 -0.00395
O1 3 0.726530 0.281753 0.424529 11.00000 0.02001 0.02716 =
0.02769 -0.00805 -0.00169 -0.00736
C1 1 1.002887 0.075691 0.524773 11.00000 0.01383 0.01863 =
0.03115 -0.01144 0.00042 -0.00497
AFIX 23
H1A 2 1.083863 0.111783 0.472326 11.00000 -1.20000
H1B 2 1.042841 0.050137 0.602593 11.00000 -1.20000
AFIX 0
C2 1 0.816737 0.398790 0.607542 11.00000 0.02065 0.01959 =
0.02460 -0.00833 -0.00037 -0.00781
C3 1 0.968040 0.402316 0.630282 11.00000 0.02284 0.03204 =
0.06517 -0.02321 -0.00908 -0.00462
AFIX 43
H3 2 1.069829 0.313822 0.610145 11.00000 -1.20000
AFIX 0
C4 1 0.972193 0.534365 0.682364 11.00000 0.03099 0.04350 =
0.06934 -0.02195 -0.01199 -0.01817
AFIX 43
H4A 2 1.076451 0.535901 0.698236 11.00000 -1.20000
AFIX 0
C5 1 0.824682 0.663286 0.711010 11.00000 0.04757 0.02615 =
0.04160 -0.01223 -0.00684 -0.01826
AFIX 43
H5 2 0.827124 0.753876 0.746585 11.00000 -1.20000
AFIX 0
C6 1 0.673557 0.660487 0.687920 11.00000 0.03471 0.02177 =
0.04223 -0.01149 -0.00420 -0.00443
AFIX 43
H6 2 0.572078 0.749484 0.707650 11.00000 -1.20000
AFIX 0
C7 1 0.668640 0.529091 0.636261 11.00000 0.02035 0.02499 =
0.03843 -0.00861 -0.00590 -0.00584
AFIX 43
H7 2 0.564157 0.528016 0.620468 11.00000 -1.20000
AFIX 0
C8 1 0.662090 0.165422 0.642866 11.00000 0.01598 0.01442 =
0.02939 -0.00979 0.00070 -0.00301
C9 1 0.695155 0.126970 0.758165 11.00000 0.02499 0.02285 =
0.03223 -0.00898 -0.00620 -0.00684
AFIX 43
H9 2 0.792078 0.135027 0.782486 11.00000 -1.20000
AFIX 0
C10 1 0.587062 0.077108 0.837197 11.00000 0.03874 0.02859 =
0.02518 -0.00814 -0.00258 -0.01177
AFIX 43
H10 2 0.609027 0.052371 0.915996 11.00000 -1.20000
AFIX 0
C11 1 0.446552 0.063141 0.801598 11.00000 0.02924 0.01903 =
0.03721 -0.00596 0.00879 -0.00758
AFIX 43
H11 2 0.372582 0.028553 0.855903 11.00000 -1.20000
AFIX 0
C12 1 0.414479 0.099532 0.687324 11.00000 0.01884 0.02796 =
0.04111 -0.00196 -0.00560 -0.00863
AFIX 43
H12 2 0.318731 0.089079 0.662972 11.00000 -1.20000
AFIX 0
C13 1 0.521091 0.151316 0.607648 11.00000 0.02100 0.02678 =
0.03170 -0.00189 -0.00761 -0.00775
AFIX 43
H13 2 0.497817 0.177088 0.529183 11.00000 -1.20000
AFIX 0
O2 3 0.911821 0.058013 0.001829 11.00000 0.02873 0.02435 =
0.03588 -0.01218 -0.01278 0.00033
O3 3 0.943090 0.162227 0.171890 11.00000 0.02647 0.02855 =
0.02721 -0.00772 -0.00238 -0.01265
O4 3 0.816191 0.106220 0.236790 11.00000 0.04176 0.03801 =
0.03032 -0.01084 0.00328 -0.02463
AFIX 3 0.8500
H4 2 0.784241 0.171860 0.292560 11.00000 -1.20000
AFIX 0
PART 1
C14 1 0.904629 0.197902 0.055810 21.00000 0.03483 0.02015 =
0.02695 -0.00447 -0.00678 -0.00724
C15 1 0.726469 0.316642 0.043193 21.00000 0.03622 0.02470 =
0.03610 -0.00366 -0.01317 -0.00321
AFIX 23
H15A 2 0.718790 0.346764 -0.040563 21.00000 -1.20000
H15B 2 0.645469 0.263462 0.069277 21.00000 -1.20000
AFIX 0
C16 1 0.676381 0.466644 0.112593 21.00000 0.03271 0.02456 =
0.04867 -0.00987 -0.00592 -0.00243
AFIX 137
H16A 2 0.748537 0.526025 0.081783 21.00000 -1.50000
H16B 2 0.689667 0.437640 0.195027 21.00000 -1.50000
H16C 2 0.558420 0.533657 0.106026 21.00000 -1.50000
AFIX 0
C17 1 1.038165 0.259581 -0.004708 21.00000 0.04505 0.03398 =
0.03952 -0.00037 0.00328 -0.01413
AFIX 137
H17A 2 1.149531 0.187447 0.013588 21.00000 -1.50000
H17B 2 1.014482 0.367022 0.022908 21.00000 -1.50000
H17C 2 1.036439 0.263976 -0.089579 21.00000 -1.50000
AFIX 0
PART 0
PART 2
C14A 1 0.904629 0.197902 0.055810 -21.00000 0.03483 0.02015 =
0.02695 -0.00447 -0.00678 -0.00724
C15A 1 1.042422 0.264594 0.014401 -21.00000 0.03870 0.02040 =
0.02937 -0.00345 -0.00652 -0.00773
AFIX 23
H15C 2 1.024954 0.362278 0.056710 -21.00000 -1.20000
H15D 2 1.156344 0.184126 0.022038 -21.00000 -1.20000
AFIX 0
C16A 1 1.013224 0.300963 -0.112101 -21.00000 0.03078 0.02532 =
0.03918 0.00169 0.00350 -0.00595
AFIX 137
H16D 2 1.090261 0.351191 -0.151153 -21.00000 -1.50000
H16E 2 0.896475 0.373988 -0.115939 -21.00000 -1.50000
H16F 2 1.033987 0.201314 -0.151312 -21.00000 -1.50000
AFIX 0
C17A 1 0.714016 0.291480 0.069987 -21.00000 0.03992 0.01956 =
0.03523 0.00849 -0.01062 -0.00212
AFIX 137
H17D 2 0.674347 0.310156 -0.007029 -21.00000 -1.50000
H17E 2 0.688499 0.394421 0.106028 -21.00000 -1.50000
H17F 2 0.657151 0.229782 0.120039 -21.00000 -1.50000
AFIX 0
HKLF 4
REM ga214_a.res in P-1
REM R1 = 0.0534 for 2453 Fo > 4sig(Fo) and 0.0718 for all 3099 data
REM 231 parameters refined using 124 restraints
END
WGHT 0.0234 1.0293
REM Instructions for potential hydrogen bonds
EQIV $1 -x+2, -y, -z+1
HTAB C1 O4_$1
EQIV $2 -x+1, -y+1, -z+1
HTAB C7 O1_$2
HTAB O4 O1
REM Highest difference peak 0.391, deepest hole -0.287, 1-sigma level 0.060
Q1 1 0.7213 0.1997 0.5929 11.00000 0.05 0.39
Q2 1 0.8293 0.3087 0.5858 11.00000 0.05 0.37
Q3 1 0.9169 0.1538 0.5208 11.00000 0.05 0.30
Q4 1 0.6518 0.0711 0.7870 11.00000 0.05 0.26
Q5 1 0.8249 0.2240 0.4396 11.00000 0.05 0.23
Q6 1 0.6480 0.1833 0.7036 11.00000 0.05 0.22
Q7 1 0.4474 0.2449 0.5019 11.00000 0.05 0.21
Q8 1 0.8982 0.4341 0.5692 11.00000 0.05 0.21
Q9 1 0.7306 0.4351 0.6497 11.00000 0.05 0.21
Q10 1 0.8824 0.1831 0.6442 11.00000 0.05 0.21
Q11 1 0.5715 0.2210 0.6228 11.00000 0.05 0.21
Q12 1 0.8494 0.1327 0.7276 11.00000 0.05 0.21
Q13 1 0.7089 0.5481 0.5622 11.00000 0.05 0.20
Q14 1 0.8054 0.2444 0.0594 11.00000 0.05 0.20
Q15 1 0.7066 0.1203 0.6833 11.00000 0.05 0.20
Q16 1 0.6475 -0.0209 0.9577 11.00000 0.05 0.20
Q17 1 0.4899 0.0796 0.6346 11.00000 0.05 0.19
Q18 1 0.8144 0.3979 0.5254 11.00000 0.05 0.19
Q19 1 0.7953 0.3320 0.3866 11.00000 0.05 0.19
Q20 1 1.0419 0.2929 0.6789 11.00000 0.05 0.19
;
_shelx_res_checksum 87250
_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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0381P)^2^+4.6328P] where P=(Fo^2^+2Fc^2^)/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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0115(2) 0.0102(2) 0.0120(2) 0.00017(16) 0.00517(16) 0.00120(16)
O1 0.0194(6) 0.0181(6) 0.0127(6) -0.0006(5) 0.0077(5) -0.0015(5)
C1 0.0124(7) 0.0138(8) 0.0156(8) -0.0010(7) 0.0057(7) 0.0019(6)
C2 0.0125(8) 0.0122(8) 0.0128(8) 0.0008(6) 0.0053(6) 0.0009(6)
C3 0.0173(8) 0.0125(8) 0.0230(9) -0.0007(7) 0.0106(7) 0.0008(6)
C4 0.0214(9) 0.0110(8) 0.0279(10) -0.0001(7) 0.0128(8) -0.0005(7)
C5 0.0184(9) 0.0178(9) 0.0233(9) -0.0028(7) 0.0091(7) -0.0058(7)
C6 0.0135(8) 0.0188(9) 0.0281(10) 0.0005(8) 0.0080(7) -0.0002(7)
C7 0.0134(8) 0.0142(8) 0.0235(9) 0.0025(7) 0.0052(7) 0.0020(6)
C8 0.0130(8) 0.0124(8) 0.0156(8) 0.0007(6) 0.0056(7) 0.0021(6)
C9 0.0414(12) 0.0147(9) 0.0539(14) -0.0024(9) 0.0339(11) -0.0036(8)
C10 0.0393(12) 0.0117(9) 0.0446(13) 0.0005(8) 0.0234(10) -0.0007(8)
C11 0.0420(12) 0.0162(9) 0.0306(11) -0.0063(8) 0.0064(10) 0.0051(9)
C12 0.095(2) 0.0178(10) 0.0481(15) -0.0038(10) 0.0527(15) 0.0045(11)
C13 0.0788(18) 0.0152(10) 0.0297(12) -0.0015(8) 0.0357(12) 0.0028(10)
O2 0.0211(7) 0.0309(7) 0.0202(7) 0.0056(6) 0.0097(6) 0.0008(6)
_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_res_file
;
ffe021a.res created by SHELXL-2014/7
TITL ffe021a_a.res in C2/c
REM Old TITL FFE021a in C2/c #15
REM SHELXT solution in C2/c
REM R1 0.120, Rweak 0.005, Alpha 0.026, Orientation as input
REM Formula found by SHELXT: C13 O2 P
CELL 0.71073 24.4329 11.0268 10.9841 90 114.11 90
ZERR 4 0.0013 0.0006 0.0006 0 0.002 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H O P
UNIT 104 200 16 8
L.S. 10
PLAN 20
SIZE 0.106 0.122 0.519
TEMP -163.15
BOND $H
MORE -1
CONF
fmap 2
acta
wpdb -1
htab
REM
REM
REM
WGHT 0.038100 4.632800
FVAR 0.37182
P1 4 0.408961 0.584403 0.411457 11.00000 0.01150 0.01024 =
0.01204 0.00017 0.00517 0.00120
O1 3 0.402728 0.584173 0.269737 11.00000 0.01942 0.01812 =
0.01273 -0.00058 0.00769 -0.00148
C1 1 0.484059 0.543052 0.529753 11.00000 0.01242 0.01383 =
0.01563 -0.00096 0.00566 0.00193
AFIX 23
H1A 2 0.508331 0.617671 0.560951 11.00000 -1.20000
H1B 2 0.481400 0.503769 0.608202 11.00000 -1.20000
AFIX 0
C2 1 0.357291 0.479656 0.437752 11.00000 0.01249 0.01221 =
0.01276 0.00084 0.00529 0.00092
AFIX 13
H2 2 0.365833 0.480590 0.534882 11.00000 -1.20000
AFIX 0
C3 1 0.366863 0.349509 0.400301 11.00000 0.01733 0.01249 =
0.02296 -0.00075 0.01059 0.00075
AFIX 23
H3A 2 0.361217 0.347381 0.305798 11.00000 -1.20000
H3B 2 0.408490 0.323878 0.455972 11.00000 -1.20000
AFIX 0
C4 1 0.323106 0.261217 0.420566 11.00000 0.02143 0.01104 =
0.02792 -0.00009 0.01285 -0.00051
AFIX 23
H4A 2 0.329072 0.179092 0.391638 11.00000 -1.20000
H4B 2 0.331353 0.257323 0.516534 11.00000 -1.20000
AFIX 0
C5 1 0.258493 0.300636 0.341499 11.00000 0.01836 0.01776 =
0.02330 -0.00277 0.00908 -0.00579
AFIX 23
H5A 2 0.231151 0.243940 0.359108 11.00000 -1.20000
H5B 2 0.249148 0.297730 0.244946 11.00000 -1.20000
AFIX 0
C6 1 0.248422 0.428710 0.379819 11.00000 0.01353 0.01883 =
0.02812 0.00049 0.00799 -0.00024
AFIX 23
H6A 2 0.254226 0.429838 0.474442 11.00000 -1.20000
H6B 2 0.206643 0.453734 0.324621 11.00000 -1.20000
AFIX 0
C7 1 0.291684 0.518521 0.359804 11.00000 0.01340 0.01418 =
0.02347 0.00250 0.00516 0.00198
AFIX 23
H7A 2 0.285584 0.599967 0.390108 11.00000 -1.20000
H7B 2 0.282965 0.523811 0.263667 11.00000 -1.20000
AFIX 0
C8 1 0.393843 0.732975 0.462254 11.00000 0.01304 0.01240 =
0.01562 0.00066 0.00557 0.00209
AFIX 13
H8 2 0.351888 0.753472 0.399459 11.00000 -1.20000
AFIX 0
C9 1 0.433286 0.833382 0.445216 11.00000 0.04140 0.01468 =
0.05394 -0.00245 0.03394 -0.00363
AFIX 23
H9A 2 0.431010 0.831690 0.353152 11.00000 -1.20000
H9B 2 0.475540 0.819699 0.507592 11.00000 -1.20000
AFIX 0
C10 1 0.412389 0.957217 0.473012 11.00000 0.03933 0.01169 =
0.04456 0.00051 0.02342 -0.00068
AFIX 23
H10A 2 0.439663 1.020844 0.466534 11.00000 -1.20000
H10B 2 0.371704 0.974138 0.404241 11.00000 -1.20000
AFIX 0
C11 1 0.411181 0.962817 0.609637 11.00000 0.04201 0.01617 =
0.03059 -0.00630 0.00645 0.00514
AFIX 23
H11A 2 0.394671 1.041932 0.620935 11.00000 -1.20000
H11B 2 0.452560 0.955991 0.679150 11.00000 -1.20000
AFIX 0
C12 1 0.372876 0.860634 0.626630 11.00000 0.09533 0.01783 =
0.04814 -0.00381 0.05272 0.00452
AFIX 23
H12A 2 0.330577 0.872932 0.563794 11.00000 -1.20000
H12B 2 0.374817 0.862650 0.718415 11.00000 -1.20000
AFIX 0
C13 1 0.394342 0.736638 0.600692 11.00000 0.07880 0.01522 =
0.02970 -0.00153 0.03575 0.00283
AFIX 23
H13A 2 0.435486 0.721112 0.668114 11.00000 -1.20000
H13B 2 0.367779 0.672326 0.608907 11.00000 -1.20000
AFIX 0
O2 3 0.472513 0.722938 0.187794 11.00000 0.02109 0.03093 =
0.02016 0.00563 0.00972 0.00081
AFIX 3
H2A 2 0.449233 0.675658 0.221534 11.00000 -1.50000
AFIX 0
HKLF 4
REM ffe021a_a.res in C2/c
REM R1 = 0.0435 for 2528 Fo > 4sig(Fo) and 0.0597 for all 3109 data
REM 145 parameters refined using 0 restraints
END
WGHT 0.0381 4.6327
REM Instructions for potential hydrogen bonds
EQIV $1 x, -y+1, z+1/2
HTAB C2 O1_$1
HTAB C3 O2_$1
HTAB O2 O1
REM Highest difference peak 0.427, deepest hole -0.362, 1-sigma level 0.061
Q1 1 0.4111 0.8763 0.6677 11.00000 0.05 0.40
Q2 1 0.4470 0.5530 0.4788 11.00000 0.05 0.27
Q3 1 0.3914 0.7321 0.5274 11.00000 0.05 0.27
Q4 1 0.3266 0.5031 0.4043 11.00000 0.05 0.26
Q5 1 0.3820 0.7856 0.6019 11.00000 0.05 0.26
Q6 1 0.4036 0.6601 0.4744 11.00000 0.05 0.23
Q7 1 0.3796 0.5217 0.4174 11.00000 0.05 0.23
Q8 1 0.2913 0.2805 0.3836 11.00000 0.05 0.22
Q9 1 0.4083 0.7884 0.4592 11.00000 0.05 0.22
Q10 1 0.4571 0.8386 0.4079 11.00000 0.05 0.22
Q11 1 0.3643 0.4179 0.4132 11.00000 0.05 0.22
Q12 1 0.4661 0.7408 0.6576 11.00000 0.05 0.22
Q13 1 0.3899 0.6759 0.4061 11.00000 0.05 0.22
Q14 1 0.4240 0.8969 0.4598 11.00000 0.05 0.21
Q15 1 0.4069 0.6087 0.3409 11.00000 0.05 0.21
Q16 1 0.2502 0.3648 0.3569 11.00000 0.05 0.21
Q17 1 0.4054 0.6782 0.6671 11.00000 0.05 0.21
Q18 1 0.3491 0.3019 0.4201 11.00000 0.05 0.20
Q19 1 0.3976 0.8314 0.3021 11.00000 0.05 0.19
Q20 1 0.3763 0.5918 0.2396 11.00000 0.05 0.19
;
_shelx_res_checksum 2498
_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 \l/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 \l/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 '\f and \w 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 > 2\s(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/[\s^2^(Fo^2^)+(0.0467P)^2^+0.4994P] where P=(Fo^2^+2Fc^2^)/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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0221(12) 0.0153(10) 0.0339(9) -0.0048(8) 0.0029(8) -0.0012(8)
O2 0.0204(11) 0.0153(10) 0.0335(9) -0.0050(7) -0.0025(7) 0.0018(8)
O3 0.0306(13) 0.0235(11) 0.0290(9) 0.0050(8) 0.0048(8) 0.0040(9)
O4 0.0329(13) 0.0191(11) 0.0442(11) 0.0059(9) -0.0104(9) 0.0020(10)
O5 0.0295(13) 0.0197(11) 0.0287(9) 0.0026(8) 0.0000(8) -0.0048(9)
O6 0.0378(14) 0.0176(11) 0.0438(11) 0.0036(9) 0.0103(9) -0.0041(10)
C1 0.0162(16) 0.0214(16) 0.0273(12) 0.0028(11) 0.0018(10) -0.0020(12)
C2 0.0201(15) 0.0243(15) 0.0403(14) 0.0076(11) 0.0002(12) -0.0010(14)
C3 0.0210(17) 0.0240(17) 0.0228(12) 0.0043(11) -0.0001(10) 0.0027(13)
C4 0.0324(19) 0.0248(17) 0.0312(14) -0.0005(12) -0.0018(12) -0.0099(14)
C5 0.034(2) 0.0310(18) 0.0291(14) 0.0001(12) 0.0027(12) 0.0096(15)
_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) . . . . ?
_shelx_res_file
;
TITL ga229b_a.res in P2(1)/n
REM Old TITL GA229b in P21/n #14
REM SHELXT solution in P2(1)/n
REM R1 0.162, Rweak 0.021, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C5 O6
CELL 0.71073 5.5661 15.4167 8.8545 90 92.306 90
ZERR 4 0.0006 0.0015 0.0009 0 0.003 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H O
UNIT 20 40 24
L.S. 10
PLAN 20
SIZE 0.104 0.214 0.225
TEMP -173.12
BOND $H
fmap 2
acta
more -1
wpdb -1
htab
conf
MERG 0
OMIT -4 50
REM
REM
REM
WGHT 0.046700 0.499400
BASF 0.39505
FVAR 0.97254
O1 3 0.927295 0.702601 0.471684 11.00000 0.02209 0.01532 =
0.03395 -0.00482 0.00286 -0.00119
O2 3 0.921881 0.789008 0.545326 11.00000 0.02043 0.01528 =
0.03354 -0.00496 -0.00251 0.00179
O3 3 0.686454 0.640294 0.651498 11.00000 0.03063 0.02351 =
0.02901 0.00499 0.00482 0.00397
O4 3 0.841849 0.564528 0.674932 11.00000 0.03288 0.01914 =
0.04420 0.00594 -0.01040 0.00205
AFIX 3
H4 2 0.986799 0.585828 0.704372 11.00000 -1.50000
AFIX 0
O5 3 0.699789 0.852761 0.344962 11.00000 0.02948 0.01974 =
0.02868 0.00257 0.00003 -0.00476
O6 3 0.854492 0.929704 0.342109 11.00000 0.03778 0.01758 =
0.04384 0.00355 0.01030 -0.00409
AFIX 3
H6 2 0.974102 0.904454 0.276099 11.00000 -1.50000
AFIX 0
C1 1 0.697497 0.668199 0.497127 11.00000 0.01624 0.02142 =
0.02728 0.00275 0.00182 -0.00200
C2 1 0.526471 0.744941 0.487296 11.00000 0.02013 0.02435 =
0.04035 0.00761 0.00019 -0.00099
AFIX 23
H2A 2 0.415233 0.744469 0.571767 11.00000 -1.20000
H2B 2 0.431513 0.744888 0.390324 11.00000 -1.20000
AFIX 0
C3 1 0.694948 0.822802 0.498052 11.00000 0.02104 0.02398 =
0.02277 0.00433 -0.00010 0.00265
C4 1 0.654138 0.595035 0.385812 11.00000 0.03237 0.02484 =
0.03117 -0.00051 -0.00176 -0.00987
AFIX 137
H4A 2 0.650188 0.618169 0.282654 11.00000 -1.50000
H4B 2 0.500099 0.567124 0.404872 11.00000 -1.50000
H4C 2 0.784002 0.552355 0.397710 11.00000 -1.50000
AFIX 0
C5 1 0.635000 0.894083 0.606862 11.00000 0.03408 0.03102 =
0.02909 0.00012 0.00274 0.00963
AFIX 137
H5A 2 0.627165 0.870045 0.709005 11.00000 -1.50000
H5B 2 0.479194 0.919598 0.576485 11.00000 -1.50000
H5C 2 0.759675 0.938940 0.605823 11.00000 -1.50000
AFIX 0
HKLF 5
REM ga229b_a.res in P2(1)/n
REM R1 = 0.0507 for 1859 Fo > 4sig(Fo) and 0.0676 for all 2327 data
REM 103 parameters refined using 0 restraints
END
WGHT 0.0467 0.4994
REM Instructions for potential hydrogen bonds
EQIV $1 x+1/2, -y+3/2, z+1/2
HTAB O4 O5_$1
HTAB O4 O6_$1
EQIV $2 x+1/2, -y+3/2, z-1/2
HTAB O6 O3_$2
HTAB O6 O4_$2
REM Highest difference peak 0.183, deepest hole -0.266, 1-sigma level 0.049
Q1 1 0.5863 0.7836 0.4881 11.00000 0.05 0.18
Q2 1 0.5824 0.6965 0.4823 11.00000 0.05 0.18
Q3 1 0.6626 0.5761 0.6845 11.00000 0.05 0.17
Q4 1 0.4809 0.5868 0.4038 11.00000 0.05 0.16
Q5 1 1.0027 0.8348 0.4791 11.00000 0.05 0.16
Q6 1 0.6952 0.7638 0.2253 11.00000 0.05 0.16
Q7 1 0.5104 0.6236 0.6593 11.00000 0.05 0.15
Q8 1 0.3416 0.8593 0.3657 11.00000 0.05 0.15
Q9 1 0.9181 0.5967 0.7678 11.00000 0.05 0.15
Q10 1 0.8520 0.4620 0.4473 11.00000 0.05 0.15
Q11 1 0.6369 0.9271 0.3430 11.00000 0.05 0.15
Q12 1 0.6522 0.8578 0.5593 11.00000 0.05 0.14
Q13 1 0.5774 0.8414 0.2994 11.00000 0.05 0.14
Q14 1 0.4414 0.7449 0.4674 11.00000 0.05 0.14
Q15 1 1.1286 0.7058 0.4679 11.00000 0.05 0.14
Q16 1 0.9291 0.7396 0.5082 11.00000 0.05 0.14
Q17 1 0.6183 0.5472 0.3814 11.00000 0.05 0.13
Q18 1 0.3258 0.6307 0.4269 11.00000 0.05 0.13
Q19 1 0.7494 0.4943 0.6840 11.00000 0.05 0.13
Q20 1 1.0940 0.7955 0.4961 11.00000 0.05 0.13
;
_shelx_res_checksum 72253
_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 \l/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 '\f and \w 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 > 2\s(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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0189P)^2^+0.1611P] where P=(Fo^2^+2Fc^2^)/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 . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0357(9) 0.0213(8) 0.0529(8) 0.0019(7) -0.0201(7) 0.0015(6)
O2 0.0231(7) 0.0237(7) 0.0207(7) 0.0024(6) -0.0048(6) -0.0039(6)
C1 0.0195(8) 0.0195(8) 0.0192(13) 0.0008(9) 0.0008(9) 0.0007(11)
C2 0.0200(9) 0.0225(10) 0.0232(10) 0.0030(8) -0.0003(8) -0.0031(8)
C3 0.0282(12) 0.095(2) 0.0235(12) 0.0176(12) -0.0033(9) -0.0147(12)
_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 . . . ?
_shelx_res_file
;
TITL temp in P4(3)2(1)2
REM Best SHELXD solution FINAL CC 88.00
REM Fragments: 5
CELL 1.54178 8.9845 8.9845 8.5007 90 90 90
ZERR 4 0.00035 0.00035 0.0005 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5-Y,0.5+X,0.75+Z
SYMM 0.5+Y,0.5-X,0.25+Z
SYMM 0.5-X,0.5+Y,0.75-Z
SYMM 0.5+X,0.5-Y,0.25-Z
SYMM +Y,+X,-Z
SYMM -Y,-X,0.5-Z
SFAC C H O
UNIT 20 40 16
L.S. 10
PLAN 7
SIZE 0.18 0.13 0.1
TEMP -163
bond $H
more -1
wpdb -1
htab
conf
fmap 2 53
acta
OMIT 0 1 1
OMIT 2 2 2
OMIT 0 2 0
OMIT 0 1 2
REM
REM
REM
WGHT 0.018900 0.161100
EXTI 0.037029
FVAR 0.53159
O1 3 0.699060 0.308420 0.163904 11.00000 0.03570 0.02126 =
0.05285 0.00189 -0.02010 0.00146
O2 3 0.637741 0.059072 0.131129 11.00000 0.02313 0.02368 =
0.02067 0.00237 -0.00477 -0.00393
AFIX 147
H2 2 0.574585 0.076828 0.060725 11.00000 -1.50000
AFIX 0
C1 1 0.868448 0.131552 0.250000 10.50000 0.01952 0.01952 =
0.01920 0.00079 0.00079 0.00071
AFIX 23
H1A 2 0.970982 0.143547 0.209277 10.50000 -1.20000
H1B 2 0.856455 0.029017 0.290723 10.50000 -1.20000
AFIX 0
C2 1 0.753930 0.164731 0.122235 11.00000 0.01997 0.02248 =
0.02321 0.00296 -0.00029 -0.00308
C3 1 0.812456 0.179609 -0.043370 11.00000 0.02817 0.09451 =
0.02353 0.01759 -0.00334 -0.01470
AFIX 137
H3A 2 0.851891 0.083537 -0.078627 11.00000 -1.50000
H3B 2 0.891941 0.254275 -0.045681 11.00000 -1.50000
H3C 2 0.731552 0.210678 -0.113374 11.00000 -1.50000
AFIX 0
HKLF 4
REM temp in P4(3)2(1)2
REM R1 = 0.0246 for 491 Fo > 4sig(Fo) and 0.0261 for all 518 data
REM 45 parameters refined using 0 restraints
END
WGHT 0.0189 0.1611
REM Instructions for potential hydrogen bonds
EQIV $1 -y+1/2, x-1/2, z-1/4
HTAB O2 O2_$1
EQIV $2 x+1/2, -y+1/2, -z+1/4
HTAB C1 O1_$2
EQIV $3 y+1/2, -x+1/2, z+1/4
HTAB C1 O1_$3
REM Highest difference peak 0.116, deepest hole -0.092, 1-sigma level 0.026
Q1 1 0.8080 0.1530 0.1892 11.00000 0.05 0.12
Q2 1 0.9038 0.1857 -0.0706 11.00000 0.05 0.10
Q3 1 0.7423 0.1870 -0.1187 11.00000 0.05 0.09
Q4 1 0.8804 0.3236 -0.0193 11.00000 0.05 0.09
Q5 1 0.6164 0.3271 0.1147 11.00000 0.05 0.09
Q6 1 0.5260 -0.0716 0.1119 11.00000 0.05 0.08
Q7 1 0.7898 0.0137 0.3580 11.00000 0.05 0.08
;
_shelx_res_checksum 84934
_olex2_submission_special_instructions 'No special instructions were received'