# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_32-emu-ep159_sq
_database_code_depnum_ccdc_archive 'CCDC 2115798'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C29 H42 O9'
_chemical_formula_weight         534.62
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.8186(4)
_cell_length_b                   6.1275(2)
_cell_length_c                   17.0159(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.869(3)
_cell_angle_gamma                90
_cell_volume                     1500.02(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8384
_cell_measurement_theta_min      4.529
_cell_measurement_theta_max      73.518

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.051
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_F_000             576

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.52077
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.964

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.04051
_diffrn_orient_matrix_ub_12      -0.1338588
_diffrn_orient_matrix_ub_13      -0.0601328
_diffrn_orient_matrix_ub_21      -0.040602
_diffrn_orient_matrix_ub_22      0.1651368
_diffrn_orient_matrix_ub_23      -0.0674588
_diffrn_orient_matrix_ub_31      0.0903789
_diffrn_orient_matrix_ub_32      0.1343121
_diffrn_orient_matrix_ub_33      0.0230485
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.069
_diffrn_reflns_number            23846
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.558
_diffrn_reflns_theta_max         73.518
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_coverage         0.813
_reflns_number_total             6013
_reflns_number_gt                5595
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.0985P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6013
_refine_ls_number_parameters     349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.041
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(12)
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.25176(19) 0.4776(4) 0.59513(16) 0.0333(6) Uani 1 1 d . . . . .
H1A H 0.203228 0.562486 0.55857 0.04 Uiso 1 1 calc R U . . .
H1B H 0.294351 0.417014 0.564725 0.04 Uiso 1 1 calc R U . . .
H1C H 0.286345 0.572479 0.638322 0.04 Uiso 1 1 calc R U . . .
C2 C 0.20663(17) 0.2898(4) 0.63258(14) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.15786(18) 0.1426(4) 0.56136(14) 0.0293(5) Uani 1 1 d . . . . .
H3A H 0.121539 0.236472 0.517724 0.035 Uiso 1 1 calc R U . . .
H3B H 0.206066 0.067991 0.539769 0.035 Uiso 1 1 calc R U . . .
C4 C 0.09306(18) -0.0297(4) 0.58228(15) 0.0322(6) Uani 1 1 d . . . . .
H4A H 0.062694 -0.111762 0.532915 0.039 Uiso 1 1 calc R U . . .
H4B H 0.129334 -0.134077 0.621956 0.039 Uiso 1 1 calc R U . . .
C5 C 0.02014(19) 0.0787(4) 0.61747(15) 0.0306(5) Uani 1 1 d . . . . .
H5 H -0.018173 0.179218 0.5764 0.037 Uiso 1 1 calc R U . . .
C6 C -0.1269(2) -0.0359(6) 0.63704(17) 0.0426(7) Uani 1 1 d . . . . .
C7 C -0.1805(3) -0.2264(7) 0.6580(2) 0.0602(10) Uani 1 1 d . . . . .
H7A H -0.179221 -0.222149 0.715785 0.072 Uiso 1 1 calc R U . . .
H7B H -0.152205 -0.36267 0.64551 0.072 Uiso 1 1 calc R U . . .
H7C H -0.245014 -0.218693 0.626225 0.072 Uiso 1 1 calc R U . . .
C8 C 0.06569(17) 0.2068(4) 0.69268(14) 0.0276(5) Uani 1 1 d . . . . .
H8A H 0.101215 0.106074 0.734247 0.033 Uiso 1 1 calc R U . . .
H8B H 0.017147 0.277534 0.714991 0.033 Uiso 1 1 calc R U . . .
C9 C 0.13140(17) 0.3819(4) 0.67327(15) 0.0261(5) Uani 1 1 d . . . . .
H9 H 0.092101 0.483326 0.633199 0.031 Uiso 1 1 calc R U . . .
C10 C 0.17447(17) 0.5192(4) 0.74831(15) 0.0280(5) Uani 1 1 d . . . . .
H10A H 0.199359 0.655647 0.730539 0.034 Uiso 1 1 calc R U . . .
H10B H 0.124853 0.559984 0.775498 0.034 Uiso 1 1 calc R U . . .
C11 C 0.25182(16) 0.4058(4) 0.80930(14) 0.0255(5) Uani 1 1 d . . . . .
H11 H 0.282175 0.513039 0.851763 0.031 Uiso 1 1 calc R U . . .
C12 C 0.17900(18) 0.2650(6) 0.91098(16) 0.0371(6) Uani 1 1 d . . . . .
C13 C 0.1463(2) 0.0614(7) 0.9425(2) 0.0526(9) Uani 1 1 d . . . . .
H13A H 0.141449 0.084827 0.998335 0.063 Uiso 1 1 calc R U . . .
H13B H 0.19071 -0.056481 0.941378 0.063 Uiso 1 1 calc R U . . .
H13C H 0.08527 0.021306 0.908724 0.063 Uiso 1 1 calc R U . . .
C14 C 0.32547(16) 0.3077(4) 0.77006(14) 0.0225(4) Uani 1 1 d . . . . .
H14 H 0.356743 0.431925 0.749156 0.027 Uiso 1 1 calc R U . . .
C15 C 0.28119(16) 0.1629(4) 0.69699(14) 0.0226(4) Uani 1 1 d . . . . .
H15 H 0.248629 0.040247 0.717481 0.027 Uiso 1 1 calc R U . . .
C16 C 0.35887(17) 0.0628(4) 0.66298(14) 0.0265(5) Uani 1 1 d . . . . .
H16A H 0.392346 0.181176 0.642267 0.032 Uiso 1 1 calc R U . . .
H16B H 0.330823 -0.033557 0.616899 0.032 Uiso 1 1 calc R U . . .
C17 C 0.42905(16) -0.0701(4) 0.72682(14) 0.0264(5) Uani 1 1 d . . . . .
H17 H 0.39214 -0.177864 0.750341 0.032 Uiso 1 1 calc R U . . .
C18 C 0.49156(19) -0.2015(5) 0.68516(17) 0.0350(6) Uani 1 1 d . . . . .
H18A H 0.533552 -0.102461 0.665938 0.042 Uiso 1 1 calc R U . . .
H18B H 0.453192 -0.280872 0.639093 0.042 Uiso 1 1 calc R U . . .
H18C H 0.528112 -0.30574 0.723672 0.042 Uiso 1 1 calc R U . . .
C19 C 0.47374(17) 0.0864(4) 0.79503(14) 0.0245(5) Uani 1 1 d . . . . .
C20 C 0.40116(16) 0.1856(4) 0.83347(13) 0.0227(4) Uani 1 1 d . . . . .
H20 H 0.370461 0.064625 0.856778 0.027 Uiso 1 1 calc R U . . .
C21 C 0.44318(17) 0.3452(4) 0.90196(14) 0.0270(5) Uani 1 1 d . . . . .
H21A H 0.44973 0.489269 0.877565 0.032 Uiso 1 1 calc R U . . .
H21B H 0.398556 0.362773 0.936478 0.032 Uiso 1 1 calc R U . . .
C22 C 0.53520(17) 0.2833(4) 0.95493(15) 0.0266(5) Uani 1 1 d . . . . .
C23 C 0.57186(17) 0.0908(4) 0.84116(14) 0.0252(5) Uani 1 1 d . . . . .
C24 C 0.65060(16) -0.0621(4) 0.83536(15) 0.0279(5) Uani 1 1 d . . . . .
H24 H 0.640846 -0.109931 0.777746 0.033 Uiso 1 1 calc R U . . .
C25 C 0.64718(18) -0.2640(5) 0.88723(18) 0.0350(6) Uani 1 1 d . . . . .
H25A H 0.653705 -0.219776 0.943664 0.042 Uiso 1 1 calc R U . . .
H25B H 0.698051 -0.362854 0.883749 0.042 Uiso 1 1 calc R U . . .
H25C H 0.587584 -0.338774 0.867542 0.042 Uiso 1 1 calc R U . . .
C26 C 0.74640(17) 0.0477(4) 0.86088(16) 0.0305(5) Uani 1 1 d . . . . .
H26A H 0.754469 0.107094 0.916236 0.037 Uiso 1 1 calc R U . . .
H26B H 0.795066 -0.064197 0.86271 0.037 Uiso 1 1 calc R U . . .
C27 C 0.76051(18) 0.2320(5) 0.80440(16) 0.0331(5) Uani 1 1 d . . . . .
H27A H 0.746578 0.178434 0.747881 0.04 Uiso 1 1 calc R U . . .
H27B H 0.717535 0.353709 0.807383 0.04 Uiso 1 1 calc R U . . .
C28 C 0.85957(19) 0.3117(5) 0.82882(18) 0.0351(6) Uani 1 1 d . . . . .
C29 C 0.9575(2) 0.6151(6) 0.8688(3) 0.0626(11) Uani 1 1 d . . . . .
H29A H 0.993069 0.537262 0.916528 0.075 Uiso 1 1 calc R U . . .
H29B H 0.954133 0.770363 0.881651 0.075 Uiso 1 1 calc R U . . .
H29C H 0.988207 0.598252 0.824157 0.075 Uiso 1 1 calc R U . . .
O1 O -0.03891(14) -0.0922(4) 0.63754(12) 0.0380(4) Uani 1 1 d . . . . .
O2 O -0.15833(16) 0.1441(5) 0.62169(15) 0.0518(6) Uani 1 1 d . . . . .
O3 O 0.21696(12) 0.2216(3) 0.84793(10) 0.0285(4) Uani 1 1 d . . . . .
O4 O 0.17302(15) 0.4479(5) 0.93619(13) 0.0468(5) Uani 1 1 d . . . . .
O5 O 0.54126(11) 0.2473(3) 0.77842(10) 0.0260(4) Uani 1 1 d . . . . .
O6 O 0.56002(13) 0.3332(3) 1.02533(11) 0.0324(4) Uani 1 1 d . . . . .
O7 O 0.59577(12) 0.1751(3) 0.92155(10) 0.0275(4) Uani 1 1 d . . . . .
O8 O 0.92651(15) 0.2001(4) 0.83262(16) 0.0494(6) Uani 1 1 d . . . . .
O9 O 0.86409(14) 0.5254(4) 0.84507(15) 0.0430(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.543(3) . ?
C2 C3 1.544(3) . ?
C2 C9 1.553(3) . ?
C2 C15 1.564(3) . ?
C3 C4 1.526(4) . ?
C4 C5 1.509(4) . ?
C5 O1 1.457(3) . ?
C5 C8 1.515(3) . ?
C6 O2 1.201(4) . ?
C6 O1 1.347(4) . ?
C6 C7 1.501(5) . ?
C8 C9 1.537(3) . ?
C9 C10 1.534(3) . ?
C10 C11 1.518(3) . ?
C11 O3 1.461(3) . ?
C11 C14 1.532(3) . ?
C12 O4 1.211(4) . ?
C12 O3 1.352(3) . ?
C12 C13 1.485(5) . ?
C14 C15 1.540(3) . ?
C14 C20 1.550(3) . ?
C15 C16 1.535(3) . ?
C16 C17 1.544(3) . ?
C17 C18 1.524(3) . ?
C17 C19 1.529(3) . ?
C19 C23 1.478(3) . ?
C19 O5 1.480(3) . ?
C19 C20 1.514(3) . ?
C20 C21 1.534(3) . ?
C21 C22 1.492(3) . ?
C22 O6 1.205(3) . ?
C22 O7 1.346(3) . ?
C23 O7 1.425(3) . ?
C23 O5 1.426(3) . ?
C23 C24 1.518(3) . ?
C24 C25 1.527(4) . ?
C24 C26 1.536(3) . ?
C26 C27 1.529(4) . ?
C27 C28 1.508(4) . ?
C28 O8 1.194(4) . ?
C28 O9 1.337(4) . ?
C29 O9 1.453(4) . ?

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 C2 C3 106.2(2) . . ?
C1 C2 C9 110.0(2) . . ?
C3 C2 C9 108.1(2) . . ?
C1 C2 C15 110.9(2) . . ?
C3 C2 C15 112.26(19) . . ?
C9 C2 C15 109.28(18) . . ?
C4 C3 C2 115.0(2) . . ?
C5 C4 C3 109.8(2) . . ?
O1 C5 C4 107.7(2) . . ?
O1 C5 C8 110.2(2) . . ?
C4 C5 C8 110.3(2) . . ?
O2 C6 O1 124.1(3) . . ?
O2 C6 C7 124.5(3) . . ?
O1 C6 C7 111.4(3) . . ?
C5 C8 C9 110.9(2) . . ?
C10 C9 C8 111.2(2) . . ?
C10 C9 C2 111.7(2) . . ?
C8 C9 C2 113.7(2) . . ?
C11 C10 C9 114.4(2) . . ?
O3 C11 C10 111.75(19) . . ?
O3 C11 C14 104.96(18) . . ?
C10 C11 C14 112.4(2) . . ?
O4 C12 O3 122.9(3) . . ?
O4 C12 C13 126.3(3) . . ?
O3 C12 C13 110.8(3) . . ?
C11 C14 C15 111.58(19) . . ?
C11 C14 C20 111.00(18) . . ?
C15 C14 C20 112.41(18) . . ?
C16 C15 C14 108.76(18) . . ?
C16 C15 C2 113.71(18) . . ?
C14 C15 C2 111.85(18) . . ?
C15 C16 C17 112.66(19) . . ?
C18 C17 C19 118.9(2) . . ?
C18 C17 C16 109.5(2) . . ?
C19 C17 C16 107.41(19) . . ?
C23 C19 O5 57.65(14) . . ?
C23 C19 C20 118.3(2) . . ?
O5 C19 C20 113.45(19) . . ?
C23 C19 C17 127.4(2) . . ?
O5 C19 C17 117.57(19) . . ?
C20 C19 C17 110.90(19) . . ?
C19 C20 C21 112.53(19) . . ?
C19 C20 C14 111.32(18) . . ?
C21 C20 C14 108.37(19) . . ?
C22 C21 C20 116.3(2) . . ?
O6 C22 O7 118.0(2) . . ?
O6 C22 C21 123.6(2) . . ?
O7 C22 C21 118.4(2) . . ?
O7 C23 O5 115.9(2) . . ?
O7 C23 C19 120.2(2) . . ?
O5 C23 C19 61.23(14) . . ?
O7 C23 C24 105.55(19) . . ?
O5 C23 C24 118.5(2) . . ?
C19 C23 C24 128.9(2) . . ?
C23 C24 C25 109.3(2) . . ?
C23 C24 C26 112.6(2) . . ?
C25 C24 C26 110.3(2) . . ?
C27 C26 C24 113.7(2) . . ?
C28 C27 C26 109.7(2) . . ?
O8 C28 O9 123.4(3) . . ?
O8 C28 C27 124.8(3) . . ?
O9 C28 C27 111.8(2) . . ?
C6 O1 C5 116.7(2) . . ?
C12 O3 C11 117.7(2) . . ?
C23 O5 C19 61.11(15) . . ?
C22 O7 C23 123.09(18) . . ?
C28 O9 C29 115.2(3) . . ?




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_refine_special_details          SQUEEZE
####################################################################### 
# 
# 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_24-emu-dp43
_database_code_depnum_ccdc_archive 'CCDC 2115801'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C24 H36 O5'
_chemical_formula_moiety         'C24 H36 O5'
_chemical_formula_weight         404.53
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9657(2)
_cell_length_b                   13.2198(2)
_cell_length_c                   18.8147(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.01(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7347
_cell_measurement_theta_min      5.768
_cell_measurement_theta_max      71.64

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.082
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 2 -5 0.0415
-4 -1 8 0.0235
-4 4 6 0.0289
-4 -2 8 0.0307
1 6 8 0.0448
1 -3 11 0.0369
-2 -1 11 0.0325
1 -8 -1 0.036
2 1 -11 0.0217
0 8 -5 0.0309
-1 7 6 0.0363
-5 -3 -3 0.0397
0 -8 3 0.038
5 0 4 0.0363
2 8 -1 0.0403
0 8 -3 0.0399


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
        (compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.972
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.964

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_orient_matrix_ub_11      -0.0200971
_diffrn_orient_matrix_ub_12      0.0238372
_diffrn_orient_matrix_ub_13      0.0796198
_diffrn_orient_matrix_ub_21      0.1706439
_diffrn_orient_matrix_ub_22      0.0041734
_diffrn_orient_matrix_ub_23      0.0091684
_diffrn_orient_matrix_ub_31      -0.0020809
_diffrn_orient_matrix_ub_32      0.1139323
_diffrn_orient_matrix_ub_33      -0.0169531
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_number            12295
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.701
_diffrn_reflns_theta_max         71.774
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.751
_reflns_number_total             4355
_reflns_number_gt                4174
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
        (compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
        (compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
        (compiled Feb  9 2015,16:26:32)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.4741P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.296
_refine_ls_restrained_S_all      1.296
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1731 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.1036(3) 0.40754(19) 0.87191(15) 0.0303(6) Uani 1 1 d . . . . .
H1A H 0.111156 0.373675 0.82572 0.036 Uiso 1 1 calc R U . . .
H1B H 0.000567 0.429701 0.879646 0.036 Uiso 1 1 calc R U . . .
H1C H 0.13268 0.360388 0.909639 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2080(3) 0.50005(18) 0.87307(13) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.3675(3) 0.46029(19) 0.86115(14) 0.0262(5) Uani 1 1 d . . . . .
H3A H 0.386916 0.40505 0.895455 0.031 Uiso 1 1 calc R U . . .
H3B H 0.373861 0.431149 0.812772 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4888(3) 0.53997(19) 0.86922(13) 0.0238(5) Uani 1 1 d . . . . .
H4A H 0.475143 0.593409 0.832934 0.029 Uiso 1 1 calc R U . . .
H4B H 0.587844 0.508586 0.861704 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4819(3) 0.58665(18) 0.94334(13) 0.0221(5) Uani 1 1 d . . . . .
H5 H 0.503335 0.531938 0.97859 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3266(3) 0.62779(18) 0.95898(12) 0.0206(5) Uani 1 1 d . . . . .
H6A H 0.308057 0.687082 0.92807 0.025 Uiso 1 1 calc R U . . .
H6B H 0.323321 0.651331 1.008908 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2015(3) 0.55053(18) 0.94747(12) 0.0213(5) Uani 1 1 d . . . . .
H7 H 0.216795 0.495543 0.983242 0.026 Uiso 1 1 calc R U . . .
C8 C 0.0476(3) 0.59621(18) 0.96204(13) 0.0213(5) Uani 1 1 d . . . . .
H8A H -0.025283 0.540421 0.967111 0.026 Uiso 1 1 calc R U . . .
H8B H 0.051303 0.632744 1.00794 0.026 Uiso 1 1 calc R U . . .
C9 C -0.0087(3) 0.66892(17) 0.90484(12) 0.0190(5) Uani 1 1 d . . . . .
H9 H -0.116198 0.683749 0.914366 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0042(3) 0.62152(17) 0.83056(11) 0.0179(4) Uani 1 1 d . . . . .
H10 H -0.065611 0.562524 0.829311 0.022 Uiso 1 1 calc R U . . .
C11 C 0.1620(3) 0.58006(17) 0.81627(12) 0.0185(4) Uani 1 1 d . . . . .
H11 H 0.232463 0.63826 0.821344 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1782(3) 0.5407(2) 0.73977(13) 0.0253(5) Uani 1 1 d . . . . .
H12A H 0.11785 0.478524 0.734386 0.03 Uiso 1 1 calc R U . . .
H12B H 0.283855 0.522603 0.731199 0.03 Uiso 1 1 calc R U . . .
C13 C 0.1287(3) 0.6183(2) 0.68345(13) 0.0246(5) Uani 1 1 d . . . . .
H13 H 0.189474 0.680639 0.691741 0.03 Uiso 1 1 calc R U . . .
C14 C 0.1674(3) 0.5812(3) 0.60875(14) 0.0377(7) Uani 1 1 d . . . . .
H14A H 0.1303 0.512086 0.602452 0.045 Uiso 1 1 calc R U . . .
H14B H 0.275899 0.582114 0.602422 0.045 Uiso 1 1 calc R U . . .
H14C H 0.120856 0.625726 0.573487 0.045 Uiso 1 1 calc R U . . .
C15 C -0.0295(3) 0.64568(17) 0.70029(12) 0.0198(5) Uani 1 1 d . . . . .
C16 C -0.0474(3) 0.69594(17) 0.77227(12) 0.0187(5) Uani 1 1 d . . . . .
H16 H 0.013128 0.759403 0.774321 0.022 Uiso 1 1 calc R U . . .
C17 C -0.2136(3) 0.72108(18) 0.77655(13) 0.0217(5) Uani 1 1 d . . . . .
H17A H -0.259361 0.689715 0.819071 0.026 Uiso 1 1 calc R U . . .
H17B H -0.229285 0.795146 0.77862 0.026 Uiso 1 1 calc R U . . .
C18 C -0.2794(3) 0.67732(17) 0.70915(13) 0.0212(5) Uani 1 1 d . . . . .
C19 C -0.1607(3) 0.62938(17) 0.66693(12) 0.0200(5) Uani 1 1 d . . . . .
C20 C -0.1954(3) 0.56976(19) 0.60029(13) 0.0234(5) Uani 1 1 d . . . . .
H20 H -0.101938 0.533962 0.585837 0.028 Uiso 1 1 calc R U . . .
C21 C -0.2416(4) 0.6382(2) 0.53841(14) 0.0353(6) Uani 1 1 d . . . . .
H21A H -0.330858 0.676606 0.551679 0.042 Uiso 1 1 calc R U . . .
H21B H -0.26332 0.596611 0.496545 0.042 Uiso 1 1 calc R U . . .
H21C H -0.160249 0.685148 0.527407 0.042 Uiso 1 1 calc R U . . .
C22 C -0.3150(3) 0.48854(18) 0.61410(13) 0.0229(5) Uani 1 1 d . . . . .
H22A H -0.413047 0.521996 0.619895 0.028 Uiso 1 1 calc R U . . .
H22B H -0.321378 0.443464 0.572191 0.028 Uiso 1 1 calc R U . . .
C23 C -0.2828(3) 0.42503(18) 0.67975(13) 0.0226(5) Uani 1 1 d . . . . .
H23A H -0.183788 0.392859 0.674283 0.027 Uiso 1 1 calc R U . . .
H23B H -0.278186 0.470142 0.721695 0.027 Uiso 1 1 calc R U . . .
C24 C -0.3971(3) 0.34404(17) 0.69329(13) 0.0228(5) Uani 1 1 d . . . . .
O1 O 0.5921(2) 0.66451(14) 0.95255(9) 0.0249(4) Uani 1 1 d . . . . .
H1X H 0.568(4) 0.713(3) 0.9237(18) 0.03 Uiso 1 1 d . U . . .
O2 O 0.07137(19) 0.76290(13) 0.90364(9) 0.0206(3) Uani 1 1 d . . . . .
H2X H 0.076(4) 0.781(2) 0.9467(18) 0.025 Uiso 1 1 d . U . . .
O3 O -0.4122(2) 0.68087(14) 0.69268(10) 0.0281(4) Uani 1 1 d . . . . .
O4 O -0.3834(2) 0.30494(14) 0.75794(10) 0.0281(4) Uani 1 1 d . . . . .
O5 O -0.4906(2) 0.31695(15) 0.65093(10) 0.0321(4) Uani 1 1 d . . . . .
H5X H -0.458(4) 0.255(3) 0.7694(19) 0.039 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.540(3) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 C3 1.540(3) . ?
C2 C7 1.552(3) . ?
C2 C11 1.559(3) . ?
C3 C4 1.522(4) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.526(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 O1 1.437(3) . ?
C5 C6 1.524(3) . ?
C5 H5 1 . ?
C6 C7 1.532(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.531(3) . ?
C7 H7 1 . ?
C8 C9 1.529(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 O2 1.435(3) . ?
C9 C10 1.536(3) . ?
C9 H9 1 . ?
C10 C11 1.541(3) . ?
C10 C16 1.544(3) . ?
C10 H10 1 . ?
C11 C12 1.537(3) . ?
C11 H11 1 . ?
C12 C13 1.540(4) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C15 1.498(3) . ?
C13 C14 1.528(3) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C19 1.351(3) . ?
C15 C16 1.517(3) . ?
C16 C17 1.529(3) . ?
C16 H16 1 . ?
C17 C18 1.514(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 O3 1.231(3) . ?
C18 C19 1.471(3) . ?
C19 C20 1.513(3) . ?
C20 C21 1.532(4) . ?
C20 C22 1.540(3) . ?
C20 H20 1 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 C23 1.521(3) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.503(3) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 O5 1.211(3) . ?
C24 O4 1.327(3) . ?
O1 H1X 0.86(4) . ?
O2 H2X 0.85(3) . ?
O4 H5X 0.96(4) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 106.9(2) . . ?
C1 C2 C7 109.4(2) . . ?
C3 C2 C7 108.2(2) . . ?
C1 C2 C11 111.6(2) . . ?
C3 C2 C11 112.2(2) . . ?
C7 C2 C11 108.47(19) . . ?
C4 C3 C2 114.4(2) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 110.0(2) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C5 C6 110.45(19) . . ?
O1 C5 C4 111.8(2) . . ?
C6 C5 C4 111.0(2) . . ?
O1 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C4 C5 H5 107.8 . . ?
C5 C6 C7 113.79(19) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 111.79(19) . . ?
C8 C7 C2 111.4(2) . . ?
C6 C7 C2 112.77(19) . . ?
C8 C7 H7 106.8 . . ?
C6 C7 H7 106.8 . . ?
C2 C7 H7 106.8 . . ?
C9 C8 C7 114.80(19) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
O2 C9 C8 112.98(19) . . ?
O2 C9 C10 107.55(18) . . ?
C8 C9 C10 111.06(19) . . ?
O2 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C9 C10 C11 111.87(19) . . ?
C9 C10 C16 111.34(18) . . ?
C11 C10 C16 112.18(19) . . ?
C9 C10 H10 107 . . ?
C11 C10 H10 107 . . ?
C16 C10 H10 107 . . ?
C12 C11 C10 111.74(19) . . ?
C12 C11 C2 112.79(19) . . ?
C10 C11 C2 111.37(19) . . ?
C12 C11 H11 106.8 . . ?
C10 C11 H11 106.8 . . ?
C2 C11 H11 106.8 . . ?
C11 C12 C13 113.1(2) . . ?
C11 C12 H12A 109 . . ?
C13 C12 H12A 109 . . ?
C11 C12 H12B 109 . . ?
C13 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?
C15 C13 C14 119.1(2) . . ?
C15 C13 C12 106.8(2) . . ?
C14 C13 C12 110.7(2) . . ?
C15 C13 H13 106.5 . . ?
C14 C13 H13 106.5 . . ?
C12 C13 H13 106.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C15 C13 133.5(2) . . ?
C19 C15 C16 113.1(2) . . ?
C13 C15 C16 113.2(2) . . ?
C15 C16 C17 104.20(19) . . ?
C15 C16 C10 108.87(18) . . ?
C17 C16 C10 113.13(19) . . ?
C15 C16 H16 110.2 . . ?
C17 C16 H16 110.2 . . ?
C10 C16 H16 110.2 . . ?
C18 C17 C16 104.62(19) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
O3 C18 C19 125.4(2) . . ?
O3 C18 C17 125.0(2) . . ?
C19 C18 C17 109.6(2) . . ?
C15 C19 C18 108.1(2) . . ?
C15 C19 C20 130.3(2) . . ?
C18 C19 C20 121.6(2) . . ?
C19 C20 C21 112.2(2) . . ?
C19 C20 C22 111.5(2) . . ?
C21 C20 C22 110.6(2) . . ?
C19 C20 H20 107.4 . . ?
C21 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 113.0(2) . . ?
C23 C22 H22A 109 . . ?
C20 C22 H22A 109 . . ?
C23 C22 H22B 109 . . ?
C20 C22 H22B 109 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 113.7(2) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
O5 C24 O4 123.5(2) . . ?
O5 C24 C23 124.8(2) . . ?
O4 C24 C23 111.7(2) . . ?
C5 O1 H1X 106(2) . . ?
C9 O2 H2X 105(2) . . ?
C24 O4 H5X 114(2) . . ?

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
C1 C2 C3 C4 -173.2(2) . . . . ?
C7 C2 C3 C4 -55.5(3) . . . . ?
C11 C2 C3 C4 64.1(3) . . . . ?
C2 C3 C4 C5 58.3(3) . . . . ?
C3 C4 C5 O1 -178.34(19) . . . . ?
C3 C4 C5 C6 -54.5(3) . . . . ?
O1 C5 C6 C7 177.67(19) . . . . ?
C4 C5 C6 C7 53.1(3) . . . . ?
C5 C6 C7 C8 -178.6(2) . . . . ?
C5 C6 C7 C2 -52.1(3) . . . . ?
C1 C2 C7 C8 -66.3(2) . . . . ?
C3 C2 C7 C8 177.54(19) . . . . ?
C11 C2 C7 C8 55.6(2) . . . . ?
C1 C2 C7 C6 167.0(2) . . . . ?
C3 C2 C7 C6 50.9(3) . . . . ?
C11 C2 C7 C6 -71.0(2) . . . . ?
C6 C7 C8 C9 73.9(2) . . . . ?
C2 C7 C8 C9 -53.3(3) . . . . ?
C7 C8 C9 O2 -70.7(2) . . . . ?
C7 C8 C9 C10 50.2(3) . . . . ?
O2 C9 C10 C11 72.5(2) . . . . ?
C8 C9 C10 C11 -51.6(2) . . . . ?
O2 C9 C10 C16 -53.9(3) . . . . ?
C8 C9 C10 C16 -178.03(19) . . . . ?
C9 C10 C11 C12 -175.2(2) . . . . ?
C16 C10 C11 C12 -49.3(2) . . . . ?
C9 C10 C11 C2 57.6(2) . . . . ?
C16 C10 C11 C2 -176.42(18) . . . . ?
C1 C2 C11 C12 -64.6(3) . . . . ?
C3 C2 C11 C12 55.3(3) . . . . ?
C7 C2 C11 C12 174.8(2) . . . . ?
C1 C2 C11 C10 61.9(2) . . . . ?
C3 C2 C11 C10 -178.09(18) . . . . ?
C7 C2 C11 C10 -58.6(2) . . . . ?
C10 C11 C12 C13 51.9(3) . . . . ?
C2 C11 C12 C13 178.3(2) . . . . ?
C11 C12 C13 C15 -56.8(3) . . . . ?
C11 C12 C13 C14 172.1(2) . . . . ?
C14 C13 C15 C19 13.7(4) . . . . ?
C12 C13 C15 C19 -112.5(3) . . . . ?
C14 C13 C15 C16 -171.3(2) . . . . ?
C12 C13 C15 C16 62.5(3) . . . . ?
C19 C15 C16 C17 -6.4(3) . . . . ?
C13 C15 C16 C17 177.5(2) . . . . ?
C19 C15 C16 C10 114.6(2) . . . . ?
C13 C15 C16 C10 -61.5(3) . . . . ?
C9 C10 C16 C15 178.97(19) . . . . ?
C11 C10 C16 C15 52.7(2) . . . . ?
C9 C10 C16 C17 -65.7(2) . . . . ?
C11 C10 C16 C17 168.07(18) . . . . ?
C15 C16 C17 C18 3.6(2) . . . . ?
C10 C16 C17 C18 -114.5(2) . . . . ?
C16 C17 C18 O3 179.3(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C13 C15 C19 C18 -178.6(2) . . . . ?
C16 C15 C19 C18 6.4(3) . . . . ?
C13 C15 C19 C20 4.3(5) . . . . ?
C16 C15 C19 C20 -170.7(2) . . . . ?
O3 C18 C19 C15 176.8(2) . . . . ?
C17 C18 C19 C15 -3.7(3) . . . . ?
O3 C18 C19 C20 -5.9(4) . . . . ?
C17 C18 C19 C20 173.6(2) . . . . ?
C15 C19 C20 C21 -110.8(3) . . . . ?
C18 C19 C20 C21 72.5(3) . . . . ?
C15 C19 C20 C22 124.6(3) . . . . ?
C18 C19 C20 C22 -52.2(3) . . . . ?
C19 C20 C22 C23 -48.6(3) . . . . ?
C21 C20 C22 C23 -174.1(2) . . . . ?
C20 C22 C23 C24 -178.9(2) . . . . ?
C22 C23 C24 O5 13.3(4) . . . . ?
C22 C23 C24 O4 -166.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1X O5 0.86(4) 2.09(4) 2.946(3) 173(3) 3_556 yes
O2 H2X O1 0.85(3) 2.03(3) 2.877(2) 176(3) 4_467 yes
O4 H5X O3 0.96(4) 1.68(4) 2.630(3) 167(3) 3_446 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_22-emu-oxid
_database_code_depnum_ccdc_archive 'CCDC 2115802'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C29 H44 O8'
_chemical_formula_moiety         'C29 H44 O8'
_chemical_formula_weight         520.64
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.97027(8)
_cell_length_b                   13.27902(10)
_cell_length_c                   20.9040(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2767.60(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18608
_cell_measurement_theta_min      4.205
_cell_measurement_theta_max      73.514

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.112
_exptl_crystal_density_diffrn    1.25
_exptl_crystal_F_000             1128

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.83622
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.922

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.035278
_diffrn_orient_matrix_ub_12      0.0179173
_diffrn_orient_matrix_ub_13      -0.0708568
_diffrn_orient_matrix_ub_21      0.034036
_diffrn_orient_matrix_ub_22      -0.1125142
_diffrn_orient_matrix_ub_23      -0.0076655
_diffrn_orient_matrix_ub_31      -0.1465427
_diffrn_orient_matrix_ub_32      -0.0217597
_diffrn_orient_matrix_ub_33      -0.0187985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_number            28399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.944
_diffrn_reflns_theta_max         73.649
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_coverage         0.767
_reflns_number_total             5569
_reflns_number_gt                5429
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.4200P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5569
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.069
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 1.23322(16) 0.85494(14) 0.15546(8) 0.0245(3) Uani 1 1 d . . . . .
H1A H 1.292285 0.841265 0.119007 0.029 Uiso 1 1 calc R U . . .
H1B H 1.223712 0.793791 0.181311 0.029 Uiso 1 1 calc R U . . .
H1C H 1.271986 0.908726 0.181702 0.029 Uiso 1 1 calc R U . . .
C2 C 1.09457(15) 0.88798(12) 0.13090(8) 0.0178(3) Uani 1 1 d . . . . .
C3 C 1.11847(16) 0.97770(12) 0.08531(8) 0.0216(3) Uani 1 1 d . . . . .
H3A H 1.180191 1.025716 0.106419 0.026 Uiso 1 1 calc R U . . .
H3B H 1.163768 0.952495 0.046323 0.026 Uiso 1 1 calc R U . . .
C4 C 0.99206(16) 1.03442(12) 0.06528(8) 0.0211(3) Uani 1 1 d . . . . .
H4A H 1.016814 1.09271 0.038211 0.025 Uiso 1 1 calc R U . . .
H4B H 0.933474 0.989455 0.039858 0.025 Uiso 1 1 calc R U . . .
C5 C 0.91733(16) 1.07075(12) 0.12399(8) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.973463 1.120901 0.147584 0.025 Uiso 1 1 calc R U . . .
C6 C 0.73264(18) 1.18314(12) 0.14134(9) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.6082(2) 1.22627(14) 0.11188(10) 0.0336(4) Uani 1 1 d . . . . .
H7A H 0.549278 1.252033 0.145666 0.04 Uiso 1 1 calc R U . . .
H7B H 0.561275 1.173624 0.08781 0.04 Uiso 1 1 calc R U . . .
H7C H 0.632551 1.281332 0.082921 0.04 Uiso 1 1 calc R U . . .
C8 C 0.88307(15) 0.98334(12) 0.16795(8) 0.0189(3) Uani 1 1 d . . . . .
H8A H 0.821388 0.936685 0.145603 0.023 Uiso 1 1 calc R U . . .
H8B H 0.836577 1.009153 0.206448 0.023 Uiso 1 1 calc R U . . .
C9 C 1.01015(15) 0.92602(12) 0.18828(8) 0.0185(3) Uani 1 1 d . . . . .
H9 H 1.067588 0.97534 0.211863 0.022 Uiso 1 1 calc R U . . .
C10 C 0.97900(16) 0.84070(12) 0.23533(8) 0.0205(3) Uani 1 1 d . . . . .
H10A H 1.063276 0.820389 0.256789 0.025 Uiso 1 1 calc R U . . .
H10B H 0.917388 0.866588 0.268626 0.025 Uiso 1 1 calc R U . . .
C11 C 0.91603(15) 0.74804(12) 0.20470(7) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.915675 0.69184 0.236544 0.021 Uiso 1 1 calc R U . . .
C12 C 0.67954(16) 0.74852(11) 0.22821(8) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.54536(16) 0.76971(13) 0.19926(9) 0.0249(4) Uani 1 1 d . . . . .
H13A H 0.521069 0.714901 0.170075 0.03 Uiso 1 1 calc R U . . .
H13B H 0.549084 0.833261 0.175492 0.03 Uiso 1 1 calc R U . . .
H13C H 0.477965 0.774847 0.233227 0.03 Uiso 1 1 calc R U . . .
C14 C 0.98787(15) 0.71278(11) 0.14408(7) 0.0160(3) Uani 1 1 d . . . . .
H14 H 1.075323 0.682415 0.157363 0.019 Uiso 1 1 calc R U . . .
C15 C 1.01906(14) 0.79964(11) 0.09720(7) 0.0149(3) Uani 1 1 d . . . . .
H15 H 0.931279 0.826731 0.081726 0.018 Uiso 1 1 calc R U . . .
C16 C 1.09620(16) 0.76122(11) 0.03824(7) 0.0186(3) Uani 1 1 d . . . . .
H16A H 1.084885 0.81128 0.003566 0.022 Uiso 1 1 calc R U . . .
H16B H 1.192757 0.759648 0.049255 0.022 Uiso 1 1 calc R U . . .
C17 C 1.05870(15) 0.65913(12) 0.01183(7) 0.0169(3) Uani 1 1 d . . . . .
C18 C 1.15813(17) 0.61960(13) -0.03622(8) 0.0218(3) Uani 1 1 d . . . . .
H18A H 1.122002 0.558821 -0.056474 0.026 Uiso 1 1 calc R U . . .
H18B H 1.242494 0.603271 -0.014512 0.026 Uiso 1 1 calc R U . . .
H18C H 1.174609 0.670976 -0.068944 0.026 Uiso 1 1 calc R U . . .
C19 C 0.96943(14) 0.59339(11) 0.04904(7) 0.0157(3) Uani 1 1 d . . . . .
C20 C 0.90622(15) 0.63039(11) 0.11079(7) 0.0168(3) Uani 1 1 d . . . . .
H20 H 0.817211 0.660217 0.099512 0.02 Uiso 1 1 calc R U . . .
C21 C 0.87895(17) 0.53514(12) 0.15030(8) 0.0222(3) Uani 1 1 d . . . . .
H21A H 0.955791 0.519186 0.178527 0.027 Uiso 1 1 calc R U . . .
H21B H 0.797225 0.542935 0.176734 0.027 Uiso 1 1 calc R U . . .
C22 C 0.85986(17) 0.45379(12) 0.09945(9) 0.0255(4) Uani 1 1 d . . . . .
H22A H 0.767745 0.456285 0.081844 0.031 Uiso 1 1 calc R U . . .
H22B H 0.875387 0.386147 0.117934 0.031 Uiso 1 1 calc R U . . .
C23 C 0.96384(15) 0.47641(12) 0.04664(8) 0.0190(3) Uani 1 1 d . . . . .
C24 C 1.10137(16) 0.42392(11) 0.05615(8) 0.0197(3) Uani 1 1 d . . . . .
H24 H 1.150748 0.431337 0.014783 0.024 Uiso 1 1 calc R U . . .
C25 C 1.0826(2) 0.31001(12) 0.06667(9) 0.0282(4) Uani 1 1 d . . . . .
H25A H 1.166298 0.27484 0.05648 0.034 Uiso 1 1 calc R U . . .
H25B H 1.010756 0.285265 0.038777 0.034 Uiso 1 1 calc R U . . .
H25C H 1.05867 0.297424 0.111434 0.034 Uiso 1 1 calc R U . . .
C26 C 1.19127(15) 0.47034(12) 0.10764(8) 0.0197(3) Uani 1 1 d . . . . .
H26A H 1.147016 0.463554 0.149817 0.024 Uiso 1 1 calc R U . . .
H26B H 1.202721 0.543066 0.098761 0.024 Uiso 1 1 calc R U . . .
C27 C 1.33009(17) 0.41978(13) 0.11032(9) 0.0246(3) Uani 1 1 d . . . . .
H27A H 1.320646 0.350236 0.126784 0.03 Uiso 1 1 calc R U . . .
H27B H 1.368272 0.416054 0.066669 0.03 Uiso 1 1 calc R U . . .
C28 C 1.42307(16) 0.47799(13) 0.15280(9) 0.0256(4) Uani 1 1 d . . . . .
C29 C 1.4695(2) 0.52453(15) 0.25957(10) 0.0364(4) Uani 1 1 d . . . . .
H29A H 1.565232 0.51249 0.252121 0.044 Uiso 1 1 calc R U . . .
H29B H 1.446357 0.504461 0.303309 0.044 Uiso 1 1 calc R U . . .
H29C H 1.449888 0.59626 0.253735 0.044 Uiso 1 1 calc R U . . .
O1 O 0.79462(12) 1.11921(9) 0.10109(6) 0.0234(2) Uani 1 1 d . . . . .
O2 O 0.77344(14) 1.20302(10) 0.19411(7) 0.0318(3) Uani 1 1 d . . . . .
O3 O 0.77762(11) 0.77064(8) 0.18628(5) 0.0175(2) Uani 1 1 d . . . . .
O4 O 0.69914(13) 0.71436(10) 0.28081(6) 0.0294(3) Uani 1 1 d . . . . .
O5 O 0.91933(11) 0.64588(8) -0.00745(5) 0.0196(2) Uani 1 1 d . . . . .
O6 O 0.91760(12) 0.44233(9) -0.01439(6) 0.0267(3) Uani 1 1 d . . . . .
H6X H 0.890333 0.491754 -0.035836 0.032 Uiso 1 1 calc R U . . .
O7 O 1.51353(16) 0.53101(13) 0.13493(8) 0.0486(4) Uani 1 1 d . . . . .
O8 O 1.39151(13) 0.46612(10) 0.21466(6) 0.0314(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.538(2) . ?
C2 C3 1.544(2) . ?
C2 C9 1.550(2) . ?
C2 C15 1.562(2) . ?
C3 C4 1.527(2) . ?
C4 C5 1.515(2) . ?
C5 O1 1.4629(19) . ?
C5 C8 1.519(2) . ?
C6 O2 1.205(2) . ?
C6 O1 1.346(2) . ?
C6 C7 1.499(2) . ?
C8 C9 1.538(2) . ?
C9 C10 1.532(2) . ?
C10 C11 1.522(2) . ?
C11 O3 1.4638(17) . ?
C11 C14 1.529(2) . ?
C12 O4 1.205(2) . ?
C12 O3 1.3456(19) . ?
C12 C13 1.495(2) . ?
C14 C20 1.531(2) . ?
C14 C15 1.545(2) . ?
C15 C16 1.540(2) . ?
C16 C17 1.511(2) . ?
C17 O5 1.4574(18) . ?
C17 C19 1.469(2) . ?
C17 C18 1.506(2) . ?
C19 O5 1.4593(18) . ?
C19 C20 1.518(2) . ?
C19 C23 1.555(2) . ?
C20 C21 1.535(2) . ?
C21 C22 1.527(2) . ?
C22 C23 1.544(2) . ?
C23 O6 1.430(2) . ?
C23 C24 1.551(2) . ?
C24 C26 1.530(2) . ?
C24 C25 1.540(2) . ?
C26 C27 1.539(2) . ?
C27 C28 1.498(3) . ?
C28 O7 1.204(2) . ?
C28 O8 1.340(2) . ?
C29 O8 1.445(2) . ?

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 C2 C3 106.70(13) . . ?
C1 C2 C9 108.83(13) . . ?
C3 C2 C9 108.06(13) . . ?
C1 C2 C15 111.68(13) . . ?
C3 C2 C15 112.05(13) . . ?
C9 C2 C15 109.40(12) . . ?
C4 C3 C2 115.00(13) . . ?
C5 C4 C3 109.93(14) . . ?
O1 C5 C4 106.64(13) . . ?
O1 C5 C8 110.24(13) . . ?
C4 C5 C8 110.94(13) . . ?
O2 C6 O1 123.75(16) . . ?
O2 C6 C7 124.88(17) . . ?
O1 C6 C7 111.37(15) . . ?
C5 C8 C9 111.10(13) . . ?
C10 C9 C8 112.11(13) . . ?
C10 C9 C2 111.46(13) . . ?
C8 C9 C2 113.26(13) . . ?
C11 C10 C9 114.29(13) . . ?
O3 C11 C10 109.49(12) . . ?
O3 C11 C14 106.64(12) . . ?
C10 C11 C14 113.75(13) . . ?
O4 C12 O3 123.95(15) . . ?
O4 C12 C13 125.81(15) . . ?
O3 C12 C13 110.22(14) . . ?
C11 C14 C20 110.26(12) . . ?
C11 C14 C15 113.04(12) . . ?
C20 C14 C15 110.62(12) . . ?
C16 C15 C14 111.15(12) . . ?
C16 C15 C2 111.66(12) . . ?
C14 C15 C2 111.81(12) . . ?
C17 C16 C15 117.78(13) . . ?
O5 C17 C19 59.81(9) . . ?
O5 C17 C18 113.65(13) . . ?
C19 C17 C18 123.01(14) . . ?
O5 C17 C16 116.45(12) . . ?
C19 C17 C16 119.31(13) . . ?
C18 C17 C16 113.18(13) . . ?
O5 C19 C17 59.68(9) . . ?
O5 C19 C20 113.04(11) . . ?
C17 C19 C20 120.61(13) . . ?
O5 C19 C23 116.02(13) . . ?
C17 C19 C23 126.73(14) . . ?
C20 C19 C23 109.62(13) . . ?
C19 C20 C14 113.39(12) . . ?
C19 C20 C21 105.32(12) . . ?
C14 C20 C21 116.02(13) . . ?
C22 C21 C20 103.33(13) . . ?
C21 C22 C23 106.04(13) . . ?
O6 C23 C22 111.09(13) . . ?
O6 C23 C24 104.90(13) . . ?
C22 C23 C24 114.49(14) . . ?
O6 C23 C19 110.88(13) . . ?
C22 C23 C19 101.27(13) . . ?
C24 C23 C19 114.40(13) . . ?
C26 C24 C25 111.51(14) . . ?
C26 C24 C23 115.27(13) . . ?
C25 C24 C23 110.62(14) . . ?
C24 C26 C27 112.12(13) . . ?
C28 C27 C26 110.66(14) . . ?
O7 C28 O8 122.97(18) . . ?
O7 C28 C27 125.55(18) . . ?
O8 C28 C27 111.45(15) . . ?
C6 O1 C5 117.20(13) . . ?
C12 O3 C11 117.98(12) . . ?
C17 O5 C19 60.50(9) . . ?
C28 O8 C29 115.93(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6X O5 0.84 2.15 2.7068(16) 123.6 . yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_55-emu-me123
_database_code_depnum_ccdc_archive 'CCDC 2115800'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C25 H46 O6'
_chemical_formula_moiety         'C25 H42 O4, 2(H2 O)'
_chemical_formula_weight         442.62
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4781(4)
_cell_length_b                   12.8100(8)
_cell_length_c                   25.4104(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2434.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10855
_cell_measurement_theta_min      3.847
_cell_measurement_theta_max      73.446

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.035
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             976

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.51985
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.977

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0367358
_diffrn_orient_matrix_ub_12      0.0027429
_diffrn_orient_matrix_ub_13      -0.0596686
_diffrn_orient_matrix_ub_21      -0.0232257
_diffrn_orient_matrix_ub_22      0.1193333
_diffrn_orient_matrix_ub_23      0.0001799
_diffrn_orient_matrix_ub_31      0.2011328
_diffrn_orient_matrix_ub_32      0.0132895
_diffrn_orient_matrix_ub_33      0.0109176
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_number            24184
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.479
_diffrn_reflns_theta_max         73.774
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.744
_reflns_number_total             4919
_reflns_number_gt                4698
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+0.8440P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4919
_refine_ls_number_parameters     296
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(12)
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 1.0885(4) -0.1441(2) 0.25282(11) 0.0251(6) Uani 1 1 d . . . . .
H1A H 0.994786 -0.130412 0.278881 0.03 Uiso 1 1 calc R U . . .
H1B H 1.152567 -0.079139 0.245084 0.03 Uiso 1 1 calc R U . . .
H1C H 1.172523 -0.19578 0.266862 0.03 Uiso 1 1 calc R U . . .
C2 C 1.0029(3) -0.18654(19) 0.20183(10) 0.0182(5) Uani 1 1 d . . . . .
C3 C 0.8787(4) -0.2771(2) 0.21841(11) 0.0227(5) Uani 1 1 d . . . . .
H3A H 0.945984 -0.324331 0.242075 0.027 Uiso 1 1 calc R U . . .
H3B H 0.777451 -0.247999 0.238758 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8036(4) -0.3415(2) 0.17269(11) 0.0237(5) Uani 1 1 d . . . . .
H4A H 0.727911 -0.398574 0.186574 0.028 Uiso 1 1 calc R U . . .
H4B H 0.728354 -0.296514 0.150022 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9553(4) -0.3868(2) 0.14069(11) 0.0241(5) Uani 1 1 d . . . . .
H5 H 1.026328 -0.434375 0.163837 0.029 Uiso 1 1 calc R U . . .
C6 C 1.0774(3) -0.3004(2) 0.12123(11) 0.0209(5) Uani 1 1 d . . . . .
H6A H 1.010061 -0.255357 0.096516 0.025 Uiso 1 1 calc R U . . .
H6B H 1.178284 -0.331835 0.101628 0.025 Uiso 1 1 calc R U . . .
C7 C 1.1518(3) -0.2328(2) 0.16592(11) 0.0200(5) Uani 1 1 d . . . . .
H7 H 1.225842 -0.279809 0.188564 0.024 Uiso 1 1 calc R U . . .
C8 C 1.2768(3) -0.1481(2) 0.14505(11) 0.0210(5) Uani 1 1 d . . . . .
H8A H 1.362406 -0.180506 0.120197 0.025 Uiso 1 1 calc R U . . .
H8B H 1.346636 -0.119578 0.174862 0.025 Uiso 1 1 calc R U . . .
C9 C 1.1823(3) -0.05803(19) 0.11716(10) 0.0177(5) Uani 1 1 d . . . . .
H9 H 1.271261 -0.000776 0.111641 0.021 Uiso 1 1 calc R U . . .
C10 C 1.0291(3) -0.01486(19) 0.15005(9) 0.0154(5) Uani 1 1 d . . . . .
H10 H 1.083916 0.020249 0.181277 0.018 Uiso 1 1 calc R U . . .
C11 C 0.9014(3) -0.09924(18) 0.17142(9) 0.0146(4) Uani 1 1 d . . . . .
H11 H 0.841791 -0.13268 0.14049 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7544(3) -0.0480(2) 0.20500(10) 0.0173(5) Uani 1 1 d . . . . .
H12A H 0.670217 -0.102995 0.216693 0.021 Uiso 1 1 calc R U . . .
H12B H 0.810396 -0.017874 0.236863 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6473(3) 0.03815(19) 0.17704(9) 0.0168(5) Uani 1 1 d . . . . .
H13 H 0.578573 0.006495 0.147286 0.02 Uiso 1 1 calc R U . . .
C14 C 0.5157(3) 0.0868(2) 0.21615(10) 0.0226(5) Uani 1 1 d . . . . .
H14A H 0.582293 0.119918 0.244857 0.027 Uiso 1 1 calc R U . . .
H14B H 0.437935 0.032191 0.230515 0.027 Uiso 1 1 calc R U . . .
H14C H 0.442784 0.139272 0.198107 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7789(3) 0.11759(18) 0.15505(9) 0.0147(5) Uani 1 1 d . . . . .
H15 H 0.8438 0.145993 0.18633 0.018 Uiso 1 1 calc R U . . .
C16 C 0.9230(3) 0.06837(18) 0.12044(10) 0.0156(5) Uani 1 1 d . . . . .
H16 H 0.864078 0.035067 0.089351 0.019 Uiso 1 1 calc R U . . .
C17 C 1.0263(3) 0.1645(2) 0.10172(11) 0.0212(5) Uani 1 1 d . . . . .
H17A H 1.096561 0.148527 0.069698 0.025 Uiso 1 1 calc R U . . .
H17B H 1.108239 0.190051 0.129467 0.025 Uiso 1 1 calc R U . . .
C18 C 0.8799(3) 0.2452(2) 0.08995(11) 0.0224(5) Uani 1 1 d . . . . .
H18A H 0.848739 0.244113 0.052091 0.027 Uiso 1 1 calc R U . . .
H18B H 0.92145 0.316159 0.099281 0.027 Uiso 1 1 calc R U . . .
C19 C 0.7145(3) 0.21446(19) 0.12394(10) 0.0170(5) Uani 1 1 d . . . . .
H19 H 0.695085 0.27186 0.149991 0.02 Uiso 1 1 calc R U . . .
C20 C 0.5409(3) 0.20388(19) 0.09146(10) 0.0175(5) Uani 1 1 d . . . . .
H20 H 0.442905 0.184584 0.116423 0.021 Uiso 1 1 calc R U . . .
C21 C 0.5450(3) 0.1209(2) 0.04823(10) 0.0226(5) Uani 1 1 d . . . . .
H21A H 0.427499 0.11696 0.031258 0.027 Uiso 1 1 calc R U . . .
H21B H 0.5745 0.052945 0.063714 0.027 Uiso 1 1 calc R U . . .
H21C H 0.635635 0.139467 0.021998 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4887(3) 0.3081(2) 0.06572(10) 0.0215(5) Uani 1 1 d . . . . .
H22A H 0.36955 0.29948 0.049274 0.026 Uiso 1 1 calc R U . . .
H22B H 0.574977 0.322726 0.037113 0.026 Uiso 1 1 calc R U . . .
C23 C 0.4817(3) 0.4040(2) 0.10210(11) 0.0252(6) Uani 1 1 d . . . . .
H23 H 0.601633 0.411845 0.119035 0.03 Uiso 1 1 calc R U . . .
C24 C 0.3420(4) 0.3939(3) 0.14581(13) 0.0349(7) Uani 1 1 d . . . . .
H24A H 0.344194 0.45678 0.167799 0.042 Uiso 1 1 calc R U . . .
H24B H 0.369286 0.332715 0.167488 0.042 Uiso 1 1 calc R U . . .
H24C H 0.223062 0.385904 0.13013 0.042 Uiso 1 1 calc R U . . .
C25 C 0.4447(4) 0.5012(2) 0.07110(12) 0.0280(6) Uani 1 1 d . . . . .
O1 O 0.8904(3) -0.44607(16) 0.09642(9) 0.0331(5) Uani 1 1 d . . . . .
H1X H 0.779029 -0.438856 0.093976 0.04 Uiso 1 1 calc R U . . .
O2 O 1.1137(2) -0.08894(15) 0.06630(7) 0.0233(4) Uani 1 1 d . . . . .
H2X H 1.199077 -0.106635 0.04674 0.028 Uiso 1 1 calc R U . . .
O3 O 0.5370(3) 0.57898(19) 0.07226(11) 0.0454(6) Uani 1 1 d . . . . .
O4 O 0.2979(3) 0.49793(18) 0.04311(9) 0.0359(5) Uani 1 1 d . . . . .
H4X H 0.292856 0.550732 0.023567 0.043 Uiso 1 1 calc R U . . .
O5 O 0.7861(3) -0.15418(18) 0.02524(9) 0.0321(5) Uani 1 1 d D . . . .
H5X H 0.791(5) -0.2183(12) 0.0192(15) 0.038 Uiso 1 1 d D U . . .
H5Y H 0.872(4) -0.129(3) 0.0424(14) 0.038 Uiso 1 1 d D U . . .
O6 O 0.4062(3) -0.14641(19) 0.00398(9) 0.0319(5) Uani 1 1 d D . . . .
H6X H 0.514(2) -0.152(3) 0.0144(15) 0.038 Uiso 1 1 d D U . . .
H6Y H 0.405(5) -0.110(3) -0.0229(10) 0.038 Uiso 1 1 d D U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.544(3) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 C3 1.545(3) . ?
C2 C11 1.557(3) . ?
C2 C7 1.557(3) . ?
C3 C4 1.531(4) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 O1 1.442(3) . ?
C5 C6 1.518(4) . ?
C5 H5 1 . ?
C6 C7 1.532(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.528(3) . ?
C7 H7 1 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 O2 1.446(3) . ?
C9 C10 1.522(3) . ?
C9 H9 1 . ?
C10 C16 1.527(3) . ?
C10 C11 1.541(3) . ?
C10 H10 1 . ?
C11 C12 1.539(3) . ?
C11 H11 1 . ?
C12 C13 1.538(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C15 1.522(3) . ?
C13 C14 1.531(3) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 C16 1.527(3) . ?
C15 C19 1.548(3) . ?
C15 H15 1 . ?
C16 C17 1.529(3) . ?
C16 H16 1 . ?
C17 C18 1.535(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.559(3) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.544(3) . ?
C19 H19 1 . ?
C20 C21 1.529(3) . ?
C20 C22 1.537(3) . ?
C20 H20 1 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 C23 1.539(4) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C25 1.499(4) . ?
C23 C24 1.530(4) . ?
C23 H23 1 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 O3 1.213(4) . ?
C25 O4 1.309(3) . ?
O1 H1X 0.84 . ?
O2 H2X 0.84 . ?
O4 H4X 0.84 . ?
O5 H5X 0.837(13) . ?
O5 H5Y 0.843(13) . ?
O6 H6X 0.852(13) . ?
O6 H6Y 0.826(13) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C3 106.6(2) . . ?
C1 C2 C11 111.4(2) . . ?
C3 C2 C11 112.5(2) . . ?
C1 C2 C7 109.2(2) . . ?
C3 C2 C7 107.7(2) . . ?
C11 C2 C7 109.34(19) . . ?
C4 C3 C2 114.7(2) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C3 109.9(2) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C5 C4 111.7(2) . . ?
O1 C5 C6 109.4(2) . . ?
C4 C5 C6 110.3(2) . . ?
O1 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C5 C6 C7 112.9(2) . . ?
C5 C6 H6A 109 . . ?
C7 C6 H6A 109 . . ?
C5 C6 H6B 109 . . ?
C7 C6 H6B 109 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 111.5(2) . . ?
C8 C7 C2 111.8(2) . . ?
C6 C7 C2 112.9(2) . . ?
C8 C7 H7 106.7 . . ?
C6 C7 H7 106.7 . . ?
C2 C7 H7 106.7 . . ?
C7 C8 C9 114.48(19) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
O2 C9 C10 108.86(18) . . ?
O2 C9 C8 111.8(2) . . ?
C10 C9 C8 111.6(2) . . ?
O2 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C9 C10 C16 111.97(19) . . ?
C9 C10 C11 113.9(2) . . ?
C16 C10 C11 109.98(18) . . ?
C9 C10 H10 106.9 . . ?
C16 C10 H10 106.9 . . ?
C11 C10 H10 106.9 . . ?
C12 C11 C10 109.82(19) . . ?
C12 C11 C2 112.28(19) . . ?
C10 C11 C2 112.15(18) . . ?
C12 C11 H11 107.4 . . ?
C10 C11 H11 107.4 . . ?
C2 C11 H11 107.4 . . ?
C13 C12 C11 114.96(19) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C15 C13 C14 112.5(2) . . ?
C15 C13 C12 108.23(18) . . ?
C14 C13 C12 109.08(19) . . ?
C15 C13 H13 109 . . ?
C14 C13 H13 109 . . ?
C12 C13 H13 109 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 113.06(19) . . ?
C13 C15 C19 121.49(19) . . ?
C16 C15 C19 104.85(19) . . ?
C13 C15 H15 105.4 . . ?
C16 C15 H15 105.4 . . ?
C19 C15 H15 105.4 . . ?
C15 C16 C10 111.78(19) . . ?
C15 C16 C17 101.72(19) . . ?
C10 C16 C17 116.93(19) . . ?
C15 C16 H16 108.7 . . ?
C10 C16 H16 108.7 . . ?
C17 C16 H16 108.7 . . ?
C16 C17 C18 104.03(19) . . ?
C16 C17 H17A 111 . . ?
C18 C17 H17A 111 . . ?
C16 C17 H17B 111 . . ?
C18 C17 H17B 111 . . ?
H17A C17 H17B 109 . . ?
C17 C18 C19 106.8(2) . . ?
C17 C18 H18A 110.4 . . ?
C19 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
C19 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
C20 C19 C15 117.6(2) . . ?
C20 C19 C18 113.2(2) . . ?
C15 C19 C18 103.78(18) . . ?
C20 C19 H19 107.2 . . ?
C15 C19 H19 107.2 . . ?
C18 C19 H19 107.2 . . ?
C21 C20 C22 107.7(2) . . ?
C21 C20 C19 115.3(2) . . ?
C22 C20 C19 111.4(2) . . ?
C21 C20 H20 107.4 . . ?
C22 C20 H20 107.4 . . ?
C19 C20 H20 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 116.5(2) . . ?
C20 C22 H22A 108.2 . . ?
C23 C22 H22A 108.2 . . ?
C20 C22 H22B 108.2 . . ?
C23 C22 H22B 108.2 . . ?
H22A C22 H22B 107.3 . . ?
C25 C23 C24 109.0(2) . . ?
C25 C23 C22 110.7(2) . . ?
C24 C23 C22 113.1(2) . . ?
C25 C23 H23 108 . . ?
C24 C23 H23 108 . . ?
C22 C23 H23 108 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 O4 121.1(3) . . ?
O3 C25 C23 124.4(3) . . ?
O4 C25 C23 114.5(3) . . ?
C5 O1 H1X 109.5 . . ?
C9 O2 H2X 109.5 . . ?
C25 O4 H4X 109.5 . . ?
H5X O5 H5Y 116(4) . . ?
H6X O6 H6Y 109(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1X O3 0.84 1.91 2.732(3) 167.4 1_545 yes
O2 H2X O6 0.84 1.96 2.799(3) 177.2 1_655 yes
O4 H4X O5 0.84 1.82 2.652(3) 173.1 4_455 yes
O5 H5X O6 0.837(13) 2.02(2) 2.808(3) 156(4) 4_545 yes
O5 H5Y O2 0.843(13) 1.972(18) 2.791(3) 164(4) . yes
O6 H6X O5 0.852(13) 2.053(16) 2.893(3) 169(4) . yes
O6 H6Y O1 0.826(13) 2.005(16) 2.815(3) 167(4) 4_445 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_27-emu-dp106-5_sq
_database_code_depnum_ccdc_archive 'CCDC 2115803'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C24 H36 O6'
_chemical_formula_weight         420.53
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_Int_Tables_number      18
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   20.4236(3)
_cell_length_b                   11.2645(2)
_cell_length_c                   10.8753(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2501.99(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9302
_cell_measurement_theta_min      4.068
_cell_measurement_theta_max      73.252

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.161
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             912
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 -2 0.0689
0 3 6 0.0589
10 -5 0 0.094
-13 2 0 0.1185
-10 4 -2 0.1167
-9 -2 5 0.0887
-3 5 -5 0.0873
2 5 5 0.0589
13 1 -1 0.0793
0 2 -7 0.0776
-3 -6 4 0.0776
-4 -2 -7 0.1055


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.90946
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.904

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 32.3424
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0196693
_diffrn_orient_matrix_ub_12      -0.0152654
_diffrn_orient_matrix_ub_13      -0.1358298
_diffrn_orient_matrix_ub_21      0.0401009
_diffrn_orient_matrix_ub_22      0.1156226
_diffrn_orient_matrix_ub_23      0.0065954
_diffrn_orient_matrix_ub_31      0.0607909
_diffrn_orient_matrix_ub_32      -0.0713949
_diffrn_orient_matrix_ub_33      0.0397014
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_number            24718
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.065
_diffrn_reflns_theta_max         73.599
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.963
_reflns_Friedel_coverage         0.745
_reflns_number_total             4933
_reflns_number_gt                4796
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.5136P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4933
_refine_ls_number_parameters     306
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1992 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.034

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The carboxylic acid is disordered over two positions and hydrogen bonds to a 
symmetry-generated equivalent of the other disorder component, thus the 
occupancy of both PARTs is set to 50:50. FLAT and SADI restraints were used to 
enforce a chemically sensible geometry for this carboxylic acid. 
The O2 hydroxide also participates in this frustrated hydrogen bond network and 
required use of two half occupancy hydrogen atoms facing opposite acceptors to 
make sense. See the article SI for diagram explaining this disorder.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.56286(10) 0.4744(2) 0.3773(2) 0.0675(6) Uani 1 1 d . . . . .
H1X H 0.578801 0.4571 0.308359 0.081 Uiso 0.5 1 calc R U P A 1
H1Y H 0.523294 0.494674 0.375528 0.081 Uiso 0.5 1 calc R U P B 2
O2 O 0.57402(12) 0.4883(3) 0.82895(19) 0.0810(8) Uani 1 1 d . . . . .
H2X H 0.548807 0.474007 0.888143 0.097 Uiso 1 1 calc R U . . .
O3 O 0.76768(12) 0.63546(18) 1.18081(18) 0.0633(5) Uani 1 1 d . . . . .
O4 O 0.79824(11) 0.36945(16) 1.02722(18) 0.0601(5) Uani 1 1 d . . . . .
C1 C 0.72772(12) 0.7683(2) 0.6715(3) 0.0457(5) Uani 1 1 d . . . . .
H1A H 0.775035 0.755663 0.664214 0.055 Uiso 1 1 calc R U . . .
H1B H 0.716676 0.786106 0.757209 0.055 Uiso 1 1 calc R U . . .
H1C H 0.714634 0.834992 0.619096 0.055 Uiso 1 1 calc R U . . .
C2 C 0.69127(10) 0.65533(17) 0.63048(18) 0.0334(4) Uani 1 1 d . . . . .
C3 C 0.71163(11) 0.6318(2) 0.4960(2) 0.0407(5) Uani 1 1 d . . . . .
H3A H 0.706755 0.706457 0.448845 0.049 Uiso 1 1 calc R U . . .
H3B H 0.758556 0.609858 0.494628 0.049 Uiso 1 1 calc R U . . .
C4 C 0.67284(12) 0.5350(2) 0.4317(2) 0.0466(5) Uani 1 1 d . . . . .
H4A H 0.688239 0.526477 0.345826 0.056 Uiso 1 1 calc R U . . .
H4B H 0.679533 0.458325 0.474326 0.056 Uiso 1 1 calc R U . . .
C5 C 0.60095(12) 0.5670(2) 0.4327(2) 0.0425(5) Uani 1 1 d . . . . .
H5 H 0.594327 0.642416 0.385815 0.051 Uiso 1 1 calc R U . . .
C6 C 0.57688(11) 0.58363(19) 0.56388(19) 0.0357(4) Uani 1 1 d . . . . .
H6A H 0.580246 0.507195 0.608372 0.043 Uiso 1 1 calc R U . . .
H6B H 0.530181 0.607128 0.562385 0.043 Uiso 1 1 calc R U . . .
C7 C 0.61629(10) 0.67805(17) 0.63272(19) 0.0344(4) Uani 1 1 d . . . . .
H7 H 0.608597 0.755129 0.589443 0.041 Uiso 1 1 calc R U . . .
C8 C 0.59088(12) 0.6933(2) 0.7653(2) 0.0484(6) Uani 1 1 d . . . . .
H8A H 0.607612 0.769413 0.798122 0.058 Uiso 1 1 calc R U . . .
H8B H 0.542517 0.698646 0.76283 0.058 Uiso 1 1 calc R U . . .
C9 C 0.60990(12) 0.5948(3) 0.8533(2) 0.0514(6) Uani 1 1 d . . . . .
H9 H 0.598888 0.621509 0.938492 0.062 Uiso 1 1 calc R U . . .
C10 C 0.68360(11) 0.5699(2) 0.84843(18) 0.0366(4) Uani 1 1 d . . . . .
H10 H 0.706357 0.642935 0.878475 0.044 Uiso 1 1 calc R U . . .
C11 C 0.70702(10) 0.54790(17) 0.71523(18) 0.0322(4) Uani 1 1 d . . . . .
H11 H 0.681705 0.478565 0.683035 0.039 Uiso 1 1 calc R U . . .
C12 C 0.77941(11) 0.5134(2) 0.71205(19) 0.0388(4) Uani 1 1 d . . . . .
H12A H 0.805914 0.583623 0.734734 0.047 Uiso 1 1 calc R U . . .
H12B H 0.791162 0.491263 0.626746 0.047 Uiso 1 1 calc R U . . .
C13 C 0.79773(13) 0.4106(2) 0.7975(2) 0.0469(5) Uani 1 1 d . . . . .
H13 H 0.771025 0.340939 0.770457 0.056 Uiso 1 1 calc R U . . .
C14 C 0.86891(16) 0.3742(3) 0.7839(3) 0.0651(8) Uani 1 1 d . . . . .
H14A H 0.89711 0.443338 0.797593 0.078 Uiso 1 1 calc R U . . .
H14B H 0.876281 0.34313 0.700894 0.078 Uiso 1 1 calc R U . . .
H14C H 0.879302 0.312609 0.844499 0.078 Uiso 1 1 calc R U . . .
C15 C 0.77489(13) 0.4411(2) 0.9253(2) 0.0452(5) Uani 1 1 d . . . . .
C16 C 0.70239(13) 0.4684(2) 0.9359(2) 0.0471(5) Uani 1 1 d . . . . .
H16 H 0.675953 0.395884 0.917099 0.056 Uiso 1 1 calc R U . . .
C17 C 0.69355(15) 0.5042(3) 1.0718(2) 0.0597(7) Uani 1 1 d . . . . .
H17A H 0.658361 0.563967 1.080761 0.072 Uiso 1 1 calc R U . . .
H17B H 0.682794 0.434203 1.123038 0.072 Uiso 1 1 calc R U . . .
C18 C 0.75903(16) 0.5555(2) 1.1074(2) 0.0536(6) Uani 1 1 d . . . . .
C19 C 0.81069(14) 0.4976(2) 1.0299(2) 0.0474(6) Uani 1 1 d . . . . .
C20 C 0.88097(14) 0.5383(2) 1.0364(2) 0.0488(6) Uani 1 1 d . . . . .
H20 H 0.90858 0.479886 0.990523 0.059 Uiso 1 1 calc R U . . .
C21 C 0.9053(2) 0.5432(3) 1.1700(3) 0.0727(10) Uani 1 1 d . . . . .
H21A H 0.883683 0.608837 1.213063 0.087 Uiso 1 1 calc R U . . .
H21B H 0.952783 0.555717 1.170788 0.087 Uiso 1 1 calc R U . . .
H21C H 0.894937 0.468251 1.21135 0.087 Uiso 1 1 calc R U . . .
C22 C 0.88712(12) 0.6595(2) 0.9723(2) 0.0435(5) Uani 1 1 d . . . . .
H22A H 0.865281 0.655281 0.891135 0.052 Uiso 1 1 calc R U . . .
H22B H 0.86397 0.719997 1.022 0.052 Uiso 1 1 calc R U . . .
C23 C 0.95758(12) 0.6987(2) 0.9540(3) 0.0476(6) Uani 1 1 d . . . . .
H23A H 0.981464 0.634234 0.911344 0.057 Uiso 1 1 calc R U . C 1
H23B H 0.97799 0.70899 1.035867 0.057 Uiso 1 1 calc R U . C 1
C24 C 0.9670(10) 0.8144(14) 0.8804(16) 0.035(3) Uani 0.514(5) 1 d D . P D 1
O5 O 0.92091(18) 0.8609(4) 0.8356(5) 0.0638(16) Uani 0.514(5) 1 d D . P D 1
O6 O 1.02692(19) 0.8540(4) 0.8773(4) 0.0646(13) Uani 0.514(5) 1 d D . P D 1
H6X H 1.026526 0.92812 0.869067 0.078 Uiso 0.514(5) 1 calc R U P D 1
C124 C 0.9532(11) 0.8091(17) 0.883(2) 0.042(4) Uani 0.486(5) 1 d D . P D 2
O105 O 0.96612(19) 0.9080(3) 0.9250(3) 0.0474(10) Uani 0.486(5) 1 d D . P D 2
O106 O 0.9331(2) 0.7991(3) 0.7671(4) 0.0505(11) Uani 0.486(5) 1 d D . P D 2
H106 H 0.938133 0.864324 0.730851 0.061 Uiso 0.486(5) 1 calc R U P D 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 1.434(3) . ?
O2 C9 1.431(3) . ?
O3 C18 1.216(3) . ?
O4 C15 1.452(3) . ?
O4 C19 1.466(3) . ?
C1 C2 1.540(3) . ?
C2 C3 1.543(3) . ?
C2 C7 1.553(3) . ?
C2 C11 1.555(3) . ?
C3 C4 1.519(3) . ?
C4 C5 1.512(3) . ?
C5 C6 1.520(3) . ?
C6 C7 1.530(3) . ?
C7 C8 1.542(3) . ?
C8 C9 1.515(4) . ?
C9 C10 1.532(3) . ?
C10 C16 1.536(3) . ?
C10 C11 1.545(3) . ?
C11 C12 1.529(3) . ?
C12 C13 1.531(3) . ?
C13 C15 1.505(3) . ?
C13 C14 1.518(4) . ?
C15 C19 1.494(3) . ?
C15 C16 1.517(4) . ?
C16 C17 1.542(3) . ?
C17 C18 1.508(4) . ?
C18 C19 1.500(4) . ?
C19 C20 1.509(4) . ?
C20 C21 1.537(4) . ?
C20 C22 1.538(3) . ?
C22 C23 1.518(3) . ?
C23 C124 1.47(2) . ?
C23 C24 1.542(14) . ?
C24 O5 1.18(2) . ?
C24 O6 1.30(2) . ?
C124 O105 1.23(2) . ?
C124 O106 1.33(3) . ?

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
C15 O4 C19 61.62(14) . . ?
C1 C2 C3 106.61(18) . . ?
C1 C2 C7 109.63(17) . . ?
C3 C2 C7 108.00(17) . . ?
C1 C2 C11 111.80(17) . . ?
C3 C2 C11 111.87(17) . . ?
C7 C2 C11 108.85(16) . . ?
C4 C3 C2 114.79(17) . . ?
C5 C4 C3 109.39(19) . . ?
O1 C5 C4 110.5(2) . . ?
O1 C5 C6 107.97(18) . . ?
C4 C5 C6 110.50(19) . . ?
C5 C6 C7 112.01(17) . . ?
C6 C7 C8 110.97(18) . . ?
C6 C7 C2 113.36(16) . . ?
C8 C7 C2 111.41(18) . . ?
C9 C8 C7 115.02(19) . . ?
O2 C9 C8 111.4(2) . . ?
O2 C9 C10 110.1(2) . . ?
C8 C9 C10 111.38(19) . . ?
C9 C10 C16 111.15(19) . . ?
C9 C10 C11 111.44(17) . . ?
C16 C10 C11 112.58(18) . . ?
C12 C11 C10 111.17(17) . . ?
C12 C11 C2 112.62(16) . . ?
C10 C11 C2 111.53(16) . . ?
C11 C12 C13 114.51(19) . . ?
C15 C13 C14 116.6(2) . . ?
C15 C13 C12 108.19(19) . . ?
C14 C13 C12 112.3(2) . . ?
O4 C15 C19 59.64(15) . . ?
O4 C15 C13 118.4(2) . . ?
C19 C15 C13 130.4(2) . . ?
O4 C15 C16 112.0(2) . . ?
C19 C15 C16 109.5(2) . . ?
C13 C15 C16 114.8(2) . . ?
C15 C16 C10 110.33(18) . . ?
C15 C16 C17 103.9(2) . . ?
C10 C16 C17 111.7(2) . . ?
C18 C17 C16 104.1(2) . . ?
O3 C18 C19 126.1(3) . . ?
O3 C18 C17 125.6(3) . . ?
C19 C18 C17 108.2(2) . . ?
O4 C19 C15 58.74(14) . . ?
O4 C19 C18 108.5(2) . . ?
C15 C19 C18 105.6(2) . . ?
O4 C19 C20 117.8(2) . . ?
C15 C19 C20 129.1(2) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C21 111.3(2) . . ?
C19 C20 C22 109.09(19) . . ?
C21 C20 C22 111.7(2) . . ?
C23 C22 C20 113.2(2) . . ?
C124 C23 C22 104.9(9) . . ?
C22 C23 C24 115.6(8) . . ?
O5 C24 O6 125.9(12) . . ?
O5 C24 C23 119.3(16) . . ?
O6 C24 C23 114.8(12) . . ?
O105 C124 O106 119.6(16) . . ?
O105 C124 C23 123.9(19) . . ?
O106 C124 C23 116.5(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1X^a O5^a 0.84 1.9 2.665(4) 150.1 3_646 yes
O1 H1Y^b O1 0.84 1.79 2.632(4) 175 2_665 yes
O106^b H106^b O1 0.84 1.71 2.524(4) 162.9 3_656 yes




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_36-37-emu-dp63b
_database_code_depnum_ccdc_archive 'CCDC 2115799'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C24.19 H42.38 O7'
_chemical_formula_moiety         'C24 H38 O5, 0.191(C H4 O), 1.809(H2 O)'
_chemical_formula_weight         445.27
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.31799(11)
_cell_length_b                   10.12992(17)
_cell_length_c                   28.0673(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2364.97(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18277
_cell_measurement_theta_min      4.602
_cell_measurement_theta_max      73.585

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             974

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.83527
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.93

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.1712
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0135134
_diffrn_orient_matrix_ub_12      0.1093585
_diffrn_orient_matrix_ub_13      0.0379545
_diffrn_orient_matrix_ub_21      0.0255743
_diffrn_orient_matrix_ub_22      0.1033019
_diffrn_orient_matrix_ub_23      -0.0395843
_diffrn_orient_matrix_ub_31      -0.1828424
_diffrn_orient_matrix_ub_32      0.0224761
_diffrn_orient_matrix_ub_33      -0.0027363
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_number            34923
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         4.641
_diffrn_reflns_theta_max         73.642
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.741
_reflns_number_total             4791
_reflns_number_gt                4677
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.6584P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4791
_refine_ls_number_parameters     376
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Both isomers were apparent and modelled as such. The atoms of the minor 
component with positions distinct from the major component were refined 
isotropically, since anisotropic refinement was unstable. The occupancy of the 
major and minor parts (including associated methanol and water molecules) were 
allowed to freely refine until stable using free variable (FVAR) to give a 
0.81:0.19 ratio of major:minor PARTs. At that point, heteroatom-bound hydrogen 
atoms associated with the disordered part of the structure were placed in 
calculated hydrogen-bonding positions and their positions fixed (AFIX 1). 
A SAME restraint was used to enforce satisfactory geometry at the carboxylic 
acid in the minor part. A SIMU restraint was used to ensure the Uiso for the 
alkyl tail atoms of the minor part were reasonably consistent.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 1.11351(16) -0.10333(15) -0.01408(5) 0.0277(3) Uani 1 1 d . . . . .
H1X H 1.045362 -0.1634 -0.009849 0.033 Uiso 1 1 calc R U . . .
O2 O 0.60164(16) -0.08594(13) 0.08667(5) 0.0226(3) Uani 1 1 d . . . . .
H2X H 0.551401 -0.099949 0.061203 0.027 Uiso 1 1 calc R U . . .
C1 C 0.8858(3) 0.3204(2) 0.10353(9) 0.0372(5) Uani 1 1 d . . . . .
H1A H 0.961009 0.348478 0.128438 0.045 Uiso 1 1 calc R U . . .
H1B H 0.775505 0.32637 0.115592 0.045 Uiso 1 1 calc R U . . .
H1C H 0.897655 0.377895 0.075658 0.045 Uiso 1 1 calc R U . . .
C2 C 0.9225(2) 0.1768(2) 0.08924(7) 0.0254(4) Uani 1 1 d . . . . .
C3 C 1.1020(3) 0.1735(2) 0.07532(8) 0.0304(5) Uani 1 1 d . . . . .
H3A H 1.12326 0.246664 0.05281 0.036 Uiso 1 1 calc R U . . .
H3B H 1.167118 0.189685 0.104255 0.036 Uiso 1 1 calc R U . . .
C4 C 1.1577(2) 0.0451(2) 0.05263(7) 0.0279(4) Uani 1 1 d . . . . .
H4A H 1.272665 0.052166 0.043894 0.033 Uiso 1 1 calc R U . . .
H4B H 1.145873 -0.028128 0.075716 0.033 Uiso 1 1 calc R U . . .
C5 C 1.0587(2) 0.0164(2) 0.00854(7) 0.0240(4) Uani 1 1 d . . . . .
H5 H 1.075184 0.090726 -0.014385 0.029 Uiso 1 1 calc R U . . .
C6 C 0.8810(2) 0.0111(2) 0.02083(7) 0.0232(4) Uani 1 1 d . . . . .
H6A H 0.861234 -0.063859 0.042684 0.028 Uiso 1 1 calc R U . . .
H6B H 0.818215 -0.00436 -0.008603 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8234(2) 0.1393(2) 0.04446(7) 0.0246(4) Uani 1 1 d . . . . .
H7 H 0.840707 0.211491 0.020689 0.03 Uiso 1 1 calc R U . . .
C8 C 0.6424(2) 0.1375(2) 0.05557(7) 0.0256(4) Uani 1 1 d . . . . .
H8A H 0.606605 0.229143 0.061759 0.031 Uiso 1 1 calc R U . . .
H8B H 0.584173 0.105553 0.02705 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5949(2) 0.05193(19) 0.09797(7) 0.0218(4) Uani 1 1 d . . . . .
H9 H 0.481301 0.073861 0.106583 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7004(2) 0.0784(2) 0.14184(7) 0.0227(4) Uani 1 1 d D . . . .
H10 H 0.673586 0.169518 0.153017 0.027 Uiso 1 1 calc R U . A 1
C11 C 0.8818(2) 0.0783(2) 0.13005(7) 0.0226(4) Uani 1 1 d . . . . .
H11 H 0.911001 -0.012325 0.118883 0.027 Uiso 1 1 calc R U . B 1
O3 O 0.4029(3) -0.1435(2) 0.26922(7) 0.0417(6) Uani 0.809(3) 1 d D . P C 1
C12 C 0.9783(5) 0.1066(7) 0.17553(14) 0.0250(10) Uani 0.809(3) 1 d D . P C 1
H12A H 1.094398 0.101465 0.167986 0.03 Uiso 0.809(3) 1 calc R U P C 1
H12B H 0.95509 0.197857 0.186131 0.03 Uiso 0.809(3) 1 calc R U P C 1
C13 C 0.9414(3) 0.0114(5) 0.21659(10) 0.0258(8) Uani 0.809(3) 1 d D . P C 1
H13 H 0.96624 -0.080468 0.205766 0.031 Uiso 0.809(3) 1 calc R U P C 1
C14 C 1.0495(4) 0.0438(6) 0.25912(10) 0.0352(8) Uani 0.809(3) 1 d D . P C 1
H14A H 1.161419 0.049737 0.248466 0.042 Uiso 0.809(3) 1 calc R U P C 1
H14B H 1.039673 -0.025977 0.283143 0.042 Uiso 0.809(3) 1 calc R U P C 1
H14C H 1.016481 0.128312 0.272997 0.042 Uiso 0.809(3) 1 calc R U P C 1
C15 C 0.7609(3) 0.0201(3) 0.22739(8) 0.0208(5) Uani 0.809(3) 1 d D . P C 1
H15 H 0.736953 0.114049 0.235697 0.025 Uiso 0.809(3) 1 calc R U P C 1
C16 C 0.6619(5) -0.0138(6) 0.18263(12) 0.0221(11) Uani 0.809(3) 1 d D . P C 1
H16 H 0.68925 -0.105872 0.172625 0.027 Uiso 0.809(3) 1 calc R U P C 1
C17 C 0.4891(4) -0.0129(6) 0.20111(13) 0.0233(9) Uani 0.809(3) 1 d D . P C 1
H17A H 0.448356 0.078313 0.205027 0.028 Uiso 0.809(3) 1 calc R U P C 1
H17B H 0.416322 -0.062377 0.179685 0.028 Uiso 0.809(3) 1 calc R U P C 1
C18 C 0.5079(3) -0.0819(3) 0.24898(9) 0.0241(5) Uani 0.809(3) 1 d D . P C 1
C19 C 0.6826(3) -0.0670(2) 0.26608(8) 0.0216(5) Uani 0.809(3) 1 d D . P C 1
H19 H 0.733591 -0.156129 0.26375 0.026 Uiso 0.809(3) 1 calc R U P C 1
C20 C 0.6970(3) -0.0228(3) 0.31856(8) 0.0210(5) Uani 0.809(3) 1 d D . P C 1
H20 H 0.814372 -0.021244 0.326309 0.025 Uiso 0.809(3) 1 calc R U P C 1
C21 C 0.6189(3) -0.1216(3) 0.35275(9) 0.0300(6) Uani 0.809(3) 1 d D . P C 1
H21A H 0.502036 -0.109616 0.352383 0.036 Uiso 0.809(3) 1 calc R U P C 1
H21B H 0.659628 -0.106766 0.385074 0.036 Uiso 0.809(3) 1 calc R U P C 1
H21C H 0.645157 -0.211707 0.34267 0.036 Uiso 0.809(3) 1 calc R U P C 1
C22 C 0.6339(4) 0.1170(3) 0.32673(10) 0.0319(6) Uani 0.809(3) 1 d D . P C 1
H22A H 0.517618 0.119155 0.319247 0.038 Uiso 0.809(3) 1 calc R U P C 1
H22B H 0.688971 0.17795 0.304502 0.038 Uiso 0.809(3) 1 calc R U P C 1
C23 C 0.6595(4) 0.1672(4) 0.37892(13) 0.0379(9) Uani 0.809(3) 1 d D . P C 1
H23A H 0.625845 0.260846 0.380827 0.045 Uiso 0.809(3) 1 calc R U P C 1
H23B H 0.589431 0.115833 0.400575 0.045 Uiso 0.809(3) 1 calc R U P C 1
C24 C 0.8305(5) 0.1559(4) 0.39576(13) 0.0365(14) Uani 0.809(3) 1 d D . P C 1
O4 O 0.8699(5) 0.0911(5) 0.43016(13) 0.0421(11) Uani 0.809(3) 1 d D . P C 1
O5 O 0.9440(3) 0.2161(3) 0.37030(9) 0.0458(6) Uani 0.809(3) 1 d D . P C 1
H5X H 1.04001 0.204593 0.378244 0.055 Uiso 0.809 1 d . U P C 1
O103 O 0.4169(10) 0.1424(11) 0.2509(4) 0.049(3) Uani 0.191(3) 1 d D . P C 2
C112 C 0.987(3) 0.077(2) 0.1763(7) 0.026(7) Uiso 0.191(3) 1 d D . P C 2
H12C H 1.100284 0.066715 0.166386 0.032 Uiso 0.191(3) 1 calc R U P C 2
H12D H 0.977119 0.165195 0.191277 0.032 Uiso 0.191(3) 1 calc R U P C 2
C113 C 0.9533(13) -0.0252(14) 0.2145(5) 0.021(4) Uiso 0.191(3) 1 d D . P C 2
H113 H 0.984702 -0.112367 0.20058 0.025 Uiso 0.191(3) 1 calc R U P C 2
C114 C 1.0556(19) -0.0072(16) 0.2588(6) 0.036(5) Uiso 0.191(3) 1 d D . P C 2
H14D H 1.035957 0.08047 0.272342 0.043 Uiso 0.191(3) 1 calc R U P C 2
H14E H 1.169447 -0.015642 0.250372 0.043 Uiso 0.191(3) 1 calc R U P C 2
H14F H 1.027325 -0.074923 0.282298 0.043 Uiso 0.191(3) 1 calc R U P C 2
C115 C 0.7766(12) -0.0340(13) 0.2250(4) 0.033(4) Uiso 0.191(3) 1 d D . P C 2
H115 H 0.757913 -0.12166 0.24043 0.04 Uiso 0.191(3) 1 calc R U P C 2
C116 C 0.6759(18) -0.0322(16) 0.1788(4) 0.040(10) Uiso 0.191(3) 1 d D . P C 2
H116 H 0.695794 -0.117894 0.162053 0.047 Uiso 0.191(3) 1 calc R U P C 2
C117 C 0.5073(16) -0.040(2) 0.2004(6) 0.024(6) Uiso 0.191(3) 1 d D . P C 2
H11D H 0.422908 -0.020349 0.176522 0.029 Uiso 0.191(3) 1 calc R U P C 2
H11E H 0.486332 -0.126871 0.215118 0.029 Uiso 0.191(3) 1 calc R U P C 2
C118 C 0.5207(10) 0.0689(10) 0.2375(4) 0.030(3) Uani 0.191(3) 1 d D . P C 2
C119 C 0.6941(10) 0.0702(10) 0.2566(3) 0.023(2) Uani 0.191(3) 1 d D . P C 2
H119 H 0.742813 0.158335 0.249665 0.028 Uiso 0.191(3) 1 calc R U P C 2
C120 C 0.6998(14) 0.0465(12) 0.3109(3) 0.031(3) Uiso 0.191(3) 1 d D U P C 2
H120 H 0.814215 0.02844 0.319626 0.038 Uiso 0.191(3) 1 calc R U P C 2
C121 C 0.6002(18) -0.0716(12) 0.3271(5) 0.044(3) Uiso 0.191(3) 1 d D U P C 2
H21D H 0.486583 -0.055804 0.319899 0.053 Uiso 0.191(3) 1 calc R U P C 2
H21E H 0.613411 -0.083846 0.361562 0.053 Uiso 0.191(3) 1 calc R U P C 2
H21F H 0.636684 -0.151085 0.31043 0.053 Uiso 0.191(3) 1 calc R U P C 2
C122 C 0.6505(19) 0.1746(13) 0.3356(4) 0.042(4) Uiso 0.191(3) 1 d D U P C 2
H12F H 0.542463 0.202164 0.324703 0.05 Uiso 0.191(3) 1 calc R U P C 2
H12G H 0.727826 0.245647 0.327792 0.05 Uiso 0.191(3) 1 calc R U P C 2
C123 C 0.649(2) 0.149(3) 0.3911(5) 0.081(10) Uiso 0.191(3) 1 d D U P C 2
H12H H 0.579789 0.213335 0.408147 0.098 Uiso 0.191(3) 1 calc R U P C 2
H12I H 0.615405 0.058166 0.399043 0.098 Uiso 0.191(3) 1 calc R U P C 2
C124 C 0.829(2) 0.173(3) 0.4007(8) 0.070(12) Uiso 0.191(3) 1 d D U P C 2
O104 O 0.890(3) 0.112(2) 0.4322(8) 0.056(8) Uiso 0.191(3) 1 d D U P C 2
O105 O 0.8687(11) 0.2625(8) 0.3677(3) 0.0233(17) Uiso 0.191(3) 1 d D U P C 2
H105 H 0.96665 0.272244 0.369317 0.028 Uiso 0.191 1 d . U P C 2
O31 O 1.2444(3) 0.1818(2) 0.39477(8) 0.0398(6) Uani 0.809(3) 1 d . . P C 1
H31X H 1.296034 0.139915 0.414966 0.048 Uiso 0.809 1 d . U P C 1
H31Y H 1.263608 0.259238 0.400164 0.048 Uiso 0.809 1 d . U P C 1
O41 O 1.1626(10) 0.2414(8) 0.3924(3) 0.0236(17) Uiso 0.191(3) 1 d . . P C 2
H41 H 1.244624 0.275172 0.404719 0.028 Uiso 0.191 1 d . U P C 2
C41 C 1.2284(13) 0.1242(11) 0.3712(4) 0.025(2) Uiso 0.191(3) 1 d . . P C 2
H41A H 1.277862 0.14639 0.340584 0.029 Uiso 0.191(3) 1 calc R U P C 2
H41B H 1.142303 0.059587 0.366188 0.029 Uiso 0.191(3) 1 calc R U P C 2
H41C H 1.309828 0.086509 0.392489 0.029 Uiso 0.191(3) 1 calc R U P C 2
O51 O 1.06146(18) 0.16551(16) 0.50505(5) 0.0317(3) Uani 1 1 d . . . . .
H51X H 1.022656 0.144536 0.479336 0.038 Uiso 1 1 d . U . . .
H51Y H 1.157492 0.149667 0.502496 0.038 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 1.443(3) . ?
O2 C9 1.433(2) . ?
C1 C2 1.540(3) . ?
C2 C3 1.543(3) . ?
C2 C7 1.550(3) . ?
C2 C11 1.556(3) . ?
C3 C4 1.520(3) . ?
C4 C5 1.515(3) . ?
C5 C6 1.518(3) . ?
C6 C7 1.535(3) . ?
C7 C8 1.538(3) . ?
C8 C9 1.524(3) . ?
C9 C10 1.536(3) . ?
C10 C16 1.512(3) . ?
C10 C116 1.540(12) . ?
C10 C11 1.545(2) . ?
C11 C12 1.535(5) . ?
C11 C112 1.56(2) . ?
O3 C18 1.215(3) . ?
C12 C13 1.534(5) . ?
C13 C14 1.530(3) . ?
C13 C15 1.535(3) . ?
C15 C16 1.541(3) . ?
C15 C19 1.543(3) . ?
C16 C17 1.528(5) . ?
C17 C18 1.523(5) . ?
C18 C19 1.538(3) . ?
C19 C20 1.544(3) . ?
C20 C22 1.528(4) . ?
C20 C21 1.531(4) . ?
C22 C23 1.565(4) . ?
C23 C24 1.504(5) . ?
C24 O4 1.213(4) . ?
C24 O5 1.332(4) . ?
O103 C118 1.201(9) . ?
C112 C113 1.517(10) . ?
C113 C115 1.502(9) . ?
C113 C114 1.518(9) . ?
C115 C119 1.540(9) . ?
C115 C116 1.545(9) . ?
C116 C117 1.530(10) . ?
C117 C118 1.521(10) . ?
C118 C119 1.539(8) . ?
C119 C120 1.543(9) . ?
C120 C121 1.525(10) . ?
C120 C122 1.527(10) . ?
C122 C123 1.577(11) . ?
C123 C124 1.539(11) . ?
C124 O104 1.189(9) . ?
C124 O105 1.339(10) . ?
O41 C41 1.436(13) . ?

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 C2 C3 106.13(17) . . ?
C1 C2 C7 109.70(19) . . ?
C3 C2 C7 107.70(16) . . ?
C1 C2 C11 111.77(17) . . ?
C3 C2 C11 112.51(17) . . ?
C7 C2 C11 108.91(15) . . ?
C4 C3 C2 114.79(17) . . ?
C5 C4 C3 109.93(18) . . ?
O1 C5 C4 110.44(16) . . ?
O1 C5 C6 112.21(16) . . ?
C4 C5 C6 110.50(16) . . ?
C5 C6 C7 111.86(16) . . ?
C6 C7 C8 112.54(16) . . ?
C6 C7 C2 113.02(16) . . ?
C8 C7 C2 111.05(16) . . ?
C9 C8 C7 114.77(16) . . ?
O2 C9 C8 111.79(15) . . ?
O2 C9 C10 108.97(15) . . ?
C8 C9 C10 112.23(16) . . ?
C16 C10 C9 112.22(18) . . ?
C9 C10 C116 109.7(5) . . ?
C16 C10 C11 111.6(2) . . ?
C9 C10 C11 112.73(16) . . ?
C116 C10 C11 105.8(6) . . ?
C12 C11 C10 109.4(2) . . ?
C12 C11 C2 112.2(2) . . ?
C10 C11 C2 111.70(16) . . ?
C10 C11 C112 111.6(8) . . ?
C2 C11 C112 119.6(6) . . ?
C13 C12 C11 113.7(3) . . ?
C14 C13 C12 109.5(3) . . ?
C14 C13 C15 114.1(3) . . ?
C12 C13 C15 107.9(3) . . ?
C13 C15 C16 110.4(3) . . ?
C13 C15 C19 121.3(3) . . ?
C16 C15 C19 102.76(19) . . ?
C10 C16 C17 116.9(4) . . ?
C10 C16 C15 111.5(3) . . ?
C17 C16 C15 103.0(3) . . ?
C18 C17 C16 101.6(3) . . ?
O3 C18 C17 125.1(2) . . ?
O3 C18 C19 125.8(2) . . ?
C17 C18 C19 109.1(2) . . ?
C18 C19 C15 103.62(18) . . ?
C18 C19 C20 113.56(19) . . ?
C15 C19 C20 118.2(2) . . ?
C22 C20 C21 111.5(2) . . ?
C22 C20 C19 112.6(2) . . ?
C21 C20 C19 112.1(2) . . ?
C20 C22 C23 113.3(2) . . ?
C24 C23 C22 113.4(3) . . ?
O4 C24 O5 118.9(4) . . ?
O4 C24 C23 123.2(3) . . ?
O5 C24 C23 117.8(3) . . ?
C113 C112 C11 119.3(15) . . ?
C115 C113 C112 111.0(11) . . ?
C115 C113 C114 113.2(10) . . ?
C112 C113 C114 113.3(12) . . ?
C113 C115 C119 120.6(9) . . ?
C113 C115 C116 111.4(9) . . ?
C119 C115 C116 103.6(8) . . ?
C117 C116 C10 115.1(14) . . ?
C117 C116 C115 99.4(8) . . ?
C10 C116 C115 120.1(11) . . ?
C118 C117 C116 99.7(10) . . ?
O103 C118 C117 127.7(9) . . ?
O103 C118 C119 124.1(9) . . ?
C117 C118 C119 108.3(7) . . ?
C118 C119 C115 102.2(6) . . ?
C118 C119 C120 111.8(7) . . ?
C115 C119 C120 116.7(8) . . ?
C121 C120 C122 112.6(9) . . ?
C121 C120 C119 113.6(9) . . ?
C122 C120 C119 108.0(9) . . ?
C120 C122 C123 108.3(11) . . ?
C124 C123 C122 98.0(10) . . ?
O104 C124 O105 139.2(15) . . ?
O104 C124 C123 117.8(13) . . ?
O105 C124 C123 103.0(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1X O51 0.84 1.95 2.769(2) 163.7 3_745 yes
O2 H2X O51 0.84 1.95 2.782(2) 169.8 2_654 yes
O5^a H5X^a O31^a 0.84 1.78 2.615(4) 179.4 . yes
O105^b H105^b O41^b 0.82 1.78 2.550(12) 154.9 . yes
O31^a H31X^a O1 0.83 2.16 2.928(3) 154.1 2_755 yes
O31^a H31Y^a O2 0.81 1.96 2.729(3) 156.4 3_755 yes
O41^b H41^b O2 0.84 1.92 2.693(8) 153.5 3_755 yes
O51 H51X O4^a 0.82 1.95 2.743(5) 162.1 . yes
O51 H51X O104^b 0.82 1.75 2.55(2) 164 . yes
O51 H51Y O1 0.82 2.02 2.827(2) 171.3 2_755 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_46-emu-066-sq
_database_code_depnum_ccdc_archive 'CCDC 2115804'
loop_
_audit_author_name
_audit_author_address
'Scott Cameron'
;Victoria University of Wellington
New Zealand
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C25 H42 O4'
_chemical_formula_weight         406.58
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   'P 65'
_symmetry_space_group_name_Hall  'P 65'
_symmetry_Int_Tables_number      170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   32.26794(16)
_cell_length_b                   32.26794(16)
_cell_length_c                   6.19392(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5585.20(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    38490
_cell_measurement_theta_min      4.176
_cell_measurement_theta_max      73.455

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            colourless
_exptl_crystal_description       rod
_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.124
_exptl_crystal_density_diffrn    0.725
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 4 0 0.0899
20 -4 0 0.078
2 -2 4 0.2988
3 1 -4 0.2667
1 -19 0 0.0622
-1 19 0 0.0622


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.955

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      120(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0856
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0015109
_diffrn_orient_matrix_ub_12      -0.0484365
_diffrn_orient_matrix_ub_13      -0.0099368
_diffrn_orient_matrix_ub_21      -0.0533667
_diffrn_orient_matrix_ub_22      -0.0249247
_diffrn_orient_matrix_ub_23      -0.0618232
_diffrn_orient_matrix_ub_31      0.0137481
_diffrn_orient_matrix_ub_32      0.0083782
_diffrn_orient_matrix_ub_33      -0.2407367
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_number            70968
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.186
_diffrn_reflns_theta_max         73.295
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.924
_reflns_Friedel_fraction_full    0.833
_reflns_Friedel_fraction_max     0.834
_reflns_Friedel_coverage         0.687
_reflns_number_total             6921
_reflns_number_gt                6784
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.3359P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6921
_refine_ls_number_parameters     269
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 
;
 Flack x determined using 2701 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.018

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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 0.58505(3) 1.06379(4) 0.56928(19) 0.0521(3) Uani 1 1 d . . . . .
H1X H 0.607575 1.081931 0.486944 0.063 Uiso 1 1 calc R U . . .
O2 O 0.46817(3) 0.90561(3) 0.87287(14) 0.03097(18) Uani 1 1 d . . . . .
H2X H 0.455617 0.919513 0.937198 0.037 Uiso 1 1 calc R U . . .
O3 O 0.45612(3) 0.59962(3) 0.91677(18) 0.0420(2) Uani 1 1 d . . . . .
H3X H 0.450649 0.580978 1.021258 0.05 Uiso 1 1 calc R U . . .
O4 O 0.52030(4) 0.64793(3) 1.1117(2) 0.0637(4) Uani 1 1 d . . . . .
C1 C 0.62478(4) 0.94010(4) 1.0728(2) 0.0340(3) Uani 1 1 d . . . . .
H1A H 0.644642 0.928721 1.004412 0.041 Uiso 1 1 calc R U . . .
H1B H 0.60028 0.914554 1.162379 0.041 Uiso 1 1 calc R U . . .
H1C H 0.644907 0.967947 1.163398 0.041 Uiso 1 1 calc R U . . .
C2 C 0.60050(4) 0.95432(3) 0.89771(18) 0.0262(2) Uani 1 1 d . . . . .
C3 C 0.64141(4) 0.99255(4) 0.7573(2) 0.0295(2) Uani 1 1 d . . . . .
H3A H 0.665981 1.016936 0.853693 0.035 Uiso 1 1 calc R U . . .
H3B H 0.656573 0.977071 0.677084 0.035 Uiso 1 1 calc R U . . .
C4 C 0.62562(4) 1.01757(4) 0.5966(2) 0.0310(2) Uani 1 1 d . . . . .
H4A H 0.65378 1.04228 0.516919 0.037 Uiso 1 1 calc R U . . .
H4B H 0.603178 0.994067 0.490739 0.037 Uiso 1 1 calc R U . . .
C5 C 0.60125(4) 1.04075(4) 0.7153(2) 0.0344(3) Uani 1 1 d . . . . .
H5 H 0.624663 1.065152 0.817939 0.041 Uiso 1 1 calc R U . . .
C6 C 0.55868(4) 1.00372(4) 0.8419(2) 0.0311(2) Uani 1 1 d . . . . .
H6A H 0.534699 0.980115 0.741015 0.037 Uiso 1 1 calc R U . . .
H6B H 0.543614 1.019557 0.92007 0.037 Uiso 1 1 calc R U . . .
C7 C 0.57373(4) 0.97769(4) 1.00459(18) 0.0278(2) Uani 1 1 d . . . . .
H7 H 0.596965 1.002684 1.10568 0.033 Uiso 1 1 calc R U . . .
C8 C 0.53168(4) 0.94170(4) 1.14288(18) 0.0302(2) Uani 1 1 d . . . . .
H8A H 0.544491 0.932889 1.269067 0.036 Uiso 1 1 calc R U . . .
H8B H 0.514156 0.957416 1.19795 0.036 Uiso 1 1 calc R U . . .
C9 C 0.49635(4) 0.89592(4) 1.02362(19) 0.0269(2) Uani 1 1 d . . . . .
H9 H 0.474269 0.872213 1.132192 0.032 Uiso 1 1 calc R U . . .
C10 C 0.52152(3) 0.87367(3) 0.90208(18) 0.0227(2) Uani 1 1 d . . . . .
H10 H 0.534715 0.860769 1.01254 0.027 Uiso 1 1 calc R U . . .
C11 C 0.56416(3) 0.91020(3) 0.76291(18) 0.0225(2) Uani 1 1 d . . . . .
H11 H 0.550704 0.922346 0.650172 0.027 Uiso 1 1 calc R U . . .
C12 C 0.58693(4) 0.88468(4) 0.64376(19) 0.0272(2) Uani 1 1 d . . . . .
H12A H 0.612865 0.908127 0.549546 0.033 Uiso 1 1 calc R U . . .
H12B H 0.601603 0.873258 0.751515 0.033 Uiso 1 1 calc R U . . .
C13 C 0.55156(4) 0.84197(4) 0.50529(18) 0.0256(2) Uani 1 1 d . . . . .
H13 H 0.537308 0.8541 0.396339 0.031 Uiso 1 1 calc R U . . .
C14 C 0.57787(5) 0.82093(4) 0.3830(2) 0.0376(3) Uani 1 1 d . . . . .
H14A H 0.591368 0.807856 0.486305 0.045 Uiso 1 1 calc R U . . .
H14B H 0.603721 0.846077 0.297142 0.045 Uiso 1 1 calc R U . . .
H14C H 0.555415 0.795354 0.287227 0.045 Uiso 1 1 calc R U . . .
C15 C 0.51128(4) 0.80672(3) 0.65183(17) 0.0224(2) Uani 1 1 d . . . . .
H15 H 0.525813 0.796374 0.767367 0.027 Uiso 1 1 calc R U . . .
C16 C 0.48724(3) 0.83185(3) 0.76082(18) 0.0225(2) Uani 1 1 d . . . . .
H16 H 0.475606 0.844926 0.644096 0.027 Uiso 1 1 calc R U . . .
C17 C 0.44338(4) 0.79028(4) 0.8661(2) 0.0289(2) Uani 1 1 d . . . . .
H17A H 0.419392 0.799526 0.905933 0.035 Uiso 1 1 calc R U . . .
H17B H 0.452304 0.778741 0.996417 0.035 Uiso 1 1 calc R U . . .
C18 C 0.42451(4) 0.75229(4) 0.6868(2) 0.0303(2) Uani 1 1 d . . . . .
H18A H 0.401212 0.755542 0.594819 0.036 Uiso 1 1 calc R U . . .
H18B H 0.408571 0.719726 0.749821 0.036 Uiso 1 1 calc R U . . .
C19 C 0.46908(4) 0.76132(3) 0.55215(19) 0.0263(2) Uani 1 1 d . . . . .
H19 H 0.464385 0.769408 0.401612 0.032 Uiso 1 1 calc R U . . .
C20 C 0.47636(4) 0.71764(4) 0.5391(2) 0.0297(2) Uani 1 1 d . . . . .
H20 H 0.508349 0.72867 0.471532 0.036 Uiso 1 1 calc R U . . .
C21 C 0.43889(5) 0.67888(4) 0.3937(3) 0.0480(3) Uani 1 1 d . . . . .
H21A H 0.44422 0.651543 0.388526 0.058 Uiso 1 1 calc R U . . .
H21B H 0.441483 0.691693 0.247745 0.058 Uiso 1 1 calc R U . . .
H21C H 0.406875 0.668486 0.451292 0.058 Uiso 1 1 calc R U . . .
C22 C 0.47661(4) 0.69642(4) 0.7608(2) 0.0302(2) Uani 1 1 d . . . . .
H22A H 0.443617 0.671223 0.797352 0.036 Uiso 1 1 calc R U . . .
H22B H 0.487221 0.721835 0.871651 0.036 Uiso 1 1 calc R U . . .
C23 C 0.50976(4) 0.67479(4) 0.7668(3) 0.0402(3) Uani 1 1 d . . . . .
H23 H 0.50574 0.657214 0.628432 0.048 Uiso 1 1 calc R U . . .
C24 C 0.56253(5) 0.71416(5) 0.7867(4) 0.0626(5) Uani 1 1 d . . . . .
H24A H 0.566679 0.733461 0.915682 0.075 Uiso 1 1 calc R U . . .
H24B H 0.571899 0.734674 0.658488 0.075 Uiso 1 1 calc R U . . .
H24C H 0.582626 0.699427 0.798685 0.075 Uiso 1 1 calc R U . . .
C25 C 0.49643(4) 0.63972(4) 0.9503(2) 0.0365(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 1.4257(13) . ?
O2 C9 1.4428(14) . ?
O3 C25 1.3140(14) . ?
O4 C25 1.2078(18) . ?
C1 C2 1.5365(14) . ?
C2 C3 1.5466(15) . ?
C2 C7 1.5507(15) . ?
C2 C11 1.5586(14) . ?
C3 C4 1.5216(15) . ?
C4 C5 1.5186(17) . ?
C5 C6 1.5129(16) . ?
C6 C7 1.5376(14) . ?
C7 C8 1.5322(16) . ?
C8 C9 1.5307(14) . ?
C9 C10 1.5245(14) . ?
C10 C16 1.5223(13) . ?
C10 C11 1.5505(13) . ?
C11 C12 1.5387(14) . ?
C12 C13 1.5377(15) . ?
C13 C15 1.5261(14) . ?
C13 C14 1.5270(14) . ?
C15 C16 1.5311(13) . ?
C15 C19 1.5449(13) . ?
C16 C17 1.5260(14) . ?
C17 C18 1.5363(16) . ?
C18 C19 1.5589(15) . ?
C19 C20 1.5425(13) . ?
C20 C21 1.5252(16) . ?
C20 C22 1.5362(17) . ?
C22 C23 1.5425(14) . ?
C23 C25 1.5069(18) . ?
C23 C24 1.5378(18) . ?

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 C2 C3 105.99(8) . . ?
C1 C2 C7 109.58(9) . . ?
C3 C2 C7 108.25(8) . . ?
C1 C2 C11 111.62(8) . . ?
C3 C2 C11 112.31(9) . . ?
C7 C2 C11 108.99(8) . . ?
C4 C3 C2 114.35(9) . . ?
C5 C4 C3 109.74(10) . . ?
O1 C5 C6 108.40(9) . . ?
O1 C5 C4 111.39(11) . . ?
C6 C5 C4 110.57(9) . . ?
C5 C6 C7 111.17(9) . . ?
C8 C7 C6 112.25(9) . . ?
C8 C7 C2 111.56(8) . . ?
C6 C7 C2 113.00(9) . . ?
C9 C8 C7 114.31(9) . . ?
O2 C9 C10 108.93(9) . . ?
O2 C9 C8 110.43(8) . . ?
C10 C9 C8 112.20(9) . . ?
C16 C10 C9 112.28(8) . . ?
C16 C10 C11 109.25(9) . . ?
C9 C10 C11 113.31(8) . . ?
C12 C11 C10 109.85(8) . . ?
C12 C11 C2 113.79(8) . . ?
C10 C11 C2 111.90(9) . . ?
C13 C12 C11 114.09(8) . . ?
C15 C13 C14 114.78(8) . . ?
C15 C13 C12 108.07(9) . . ?
C14 C13 C12 110.28(9) . . ?
C13 C15 C16 109.62(8) . . ?
C13 C15 C19 119.18(9) . . ?
C16 C15 C19 103.81(8) . . ?
C10 C16 C17 118.49(9) . . ?
C10 C16 C15 112.76(8) . . ?
C17 C16 C15 102.45(8) . . ?
C16 C17 C18 102.47(9) . . ?
C17 C18 C19 106.08(8) . . ?
C20 C19 C15 114.99(8) . . ?
C20 C19 C18 113.88(9) . . ?
C15 C19 C18 104.88(8) . . ?
C21 C20 C22 109.95(10) . . ?
C21 C20 C19 111.08(10) . . ?
C22 C20 C19 113.44(9) . . ?
C20 C22 C23 112.49(10) . . ?
C25 C23 C24 110.02(12) . . ?
C25 C23 C22 110.84(10) . . ?
C24 C23 C22 111.11(10) . . ?
O4 C25 O3 123.76(12) . . ?
O4 C25 C23 123.24(11) . . ?
O3 C25 C23 112.99(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1X O4 0.84 1.9 2.7253(15) 166.2 5_564 yes
O2 H2X O1 0.84 1.84 2.6644(12) 166.3 4_675 yes
O3 H3X O2 0.84 1.83 2.6539(12) 168.4 3_565 yes




# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_refine_special_details          SQUEEZE
