# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

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

data_2a
_database_code_depnum_ccdc_archive 'CCDC 2059245'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
(2?-methylphenyl)-2,3,4-tri-O-methyl-α-L-rhamnopyranoside
_chemical_formula_moiety         'C16 H24 O5'
_chemical_formula_sum            'C16 H24 O5'
_chemical_formula_weight         296.35
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H24O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.89131(5)
_cell_length_b                   11.97867(7)
_cell_length_c                   16.99670(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1606.654(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12694
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.1800
_cell_measurement_theta_min      4.5010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 -1 0.0754
5 0 1 0.0754
1 -8 -1 0.1539
1 7 -1 0.2117
-3 6 -3 0.1704
0 1 -11 0.0944
1 0 11 0.0697
-2 -3 -9 0.1248

_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.151
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9971 -0.0008 -1.0003 0.6950 -0.1869 -0.6647
4.9971 0.0008 1.0003 -0.6950 0.1869 0.6647
0.9974 -7.9933 -1.0008 -0.8526 -0.0162 -0.6129
1.0007 6.9949 -0.9977 0.4634 -0.1183 0.7915
-2.9975 5.9952 -2.9973 0.9199 -0.3691 0.1693
-0.0021 1.0014 -10.9923 -0.0200 -0.9970 0.1227
1.0017 -0.0020 10.9927 -0.0332 1.0096 0.1044
-2.0013 -2.9963 -8.9949 -0.0694 -0.8285 -0.5240

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15620
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.235
_diffrn_reflns_theta_min         4.516
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00-120.00   84
  2  ω    -30.00  54.00   1.00    1.00    --   37.09 -57.00-180.00   84
  3  ω     23.00  90.00   1.00    1.00    --   37.09-125.00   0.00   67
  4  ω      1.00  76.00   1.00    1.00    --   37.09 -99.00 -60.00   75
  5  ω      1.00  76.00   1.00    1.00    --   37.09 -99.00-120.00   75
  6  ω      1.00  76.00   1.00    1.00    --   37.09 -99.00  30.00   75
  7  ω     41.00 132.00   1.00    1.00    --  111.00 -30.00 120.00   91
  8  ω     43.00 128.00   1.00    1.00    --  111.00 -45.00 120.00   85
  9  ω     42.00 109.00   1.00    1.00    --  111.00 -94.00 -30.00   67
 10  ω     90.00 178.00   1.00    1.00    --  111.00  30.00 -60.00   88
 11  ω    100.00 178.00   1.00    1.00    --  111.00 111.00 -90.00   78
 12  ω     43.00 128.00   1.00    1.00    --  111.00 -45.00 -60.00   85
 13  ω     40.00 149.00   1.00    1.00    --  111.00 -15.00-120.00  109
 14  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00 -30.00   84
 15  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00 120.00   84
 16  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00-180.00   84
 17  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00  60.00   84
 18  ω    -32.00  56.00   1.00    1.00    --   37.09 -38.00 -90.00   88
 19  ω    -30.00  54.00   1.00    1.00    --   37.09 -57.00  90.00   84
 20  ω     84.00 178.00   1.00    1.00    --  111.00  77.00  60.00   94
 21  ω     42.00 107.00   1.00    1.00    --  111.00 -94.00  90.00   65
 22  ω     73.00 178.00   1.00    1.00    --  111.00  15.00 150.00  105
 23  ω     42.00 109.00   1.00    1.00    --  111.00 -94.00-150.00   67
 24  ω     73.00 178.00   1.00    1.00    --  111.00  15.00  30.00  105
 25  ω     93.00 178.00   1.00    1.00    --  111.00  61.00-120.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1410752000
_diffrn_orient_matrix_UB_12      0.0878342000
_diffrn_orient_matrix_UB_13      0.0098488000
_diffrn_orient_matrix_UB_21      0.0193803000
_diffrn_orient_matrix_UB_22      -0.0068367000
_diffrn_orient_matrix_UB_23      0.0900742000
_diffrn_orient_matrix_UB_31      0.1335369000
_diffrn_orient_matrix_UB_32      0.0936772000
_diffrn_orient_matrix_UB_33      -0.0026584000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3163
_reflns_number_total             3209
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.2243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          'Refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66889(13) 0.55502(8) 0.34587(5) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.40328(13) 0.44773(9) 0.19347(6) 0.0213(2) Uani 1 1 d . . . . .
O3 O 0.27859(12) 0.67695(9) 0.20981(6) 0.0210(2) Uani 1 1 d . . . . .
O4 O 0.57444(13) 0.77436(8) 0.14309(6) 0.0182(2) Uani 1 1 d . . . . .
O5 O 0.74335(13) 0.50816(8) 0.21528(5) 0.0177(2) Uani 1 1 d . . . . .
C1 C 0.63212(18) 0.48849(12) 0.27828(8) 0.0177(3) Uani 1 1 d . . . . .
H1 H 0.637142 0.409386 0.292791 0.021 Uiso 1 1 calc R . . . .
C2 C 0.45005(18) 0.51893(11) 0.25697(8) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.375219 0.506271 0.302110 0.021 Uiso 1 1 calc R . . . .
C3 C 0.44415(17) 0.64219(11) 0.23226(8) 0.0166(3) Uani 1 1 d . . . . .
H3 H 0.482718 0.688411 0.276332 0.020 Uiso 1 1 calc R . . . .
C4 C 0.56350(17) 0.65875(11) 0.16318(8) 0.0162(3) Uani 1 1 d . . . . .
H4 H 0.523420 0.615798 0.117770 0.019 Uiso 1 1 calc R . . . .
C5 C 0.74306(17) 0.62104(11) 0.18576(8) 0.0166(3) Uani 1 1 d . . . . .
H5 H 0.786881 0.670900 0.226703 0.020 Uiso 1 1 calc R . . . .
C6 C 0.86337(19) 0.62261(13) 0.11647(9) 0.0218(3) Uani 1 1 d . . . . .
H6A H 0.974912 0.602158 0.133803 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.866291 0.696232 0.094204 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.825238 0.570416 0.077433 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.81215(18) 0.53187(12) 0.38942(8) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.8202(2) 0.58787(12) 0.46192(8) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.9621(2) 0.56985(13) 0.50872(9) 0.0253(3) Uani 1 1 d . . . . .
H9 H 0.969908 0.605775 0.557094 0.030 Uiso 1 1 calc R . . . .
C10 C 1.09228(19) 0.49960(13) 0.48506(9) 0.0249(3) Uani 1 1 d . . . . .
H10 H 1.186609 0.489425 0.517067 0.030 Uiso 1 1 calc R . . . .
C11 C 1.08104(19) 0.44479(13) 0.41365(9) 0.0229(3) Uani 1 1 d . . . . .
H11 H 1.167749 0.397283 0.397771 0.027 Uiso 1 1 calc R . . . .
C12 C 0.94037(18) 0.46047(12) 0.36539(8) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.932528 0.423356 0.317466 0.024 Uiso 1 1 calc R . . . .
C13 C 0.6777(2) 0.66290(15) 0.48759(9) 0.0322(4) Uani 1 1 d . . . . .
H13A H 0.664660 0.722512 0.450336 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.703047 0.693419 0.538478 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.574504 0.620654 0.490358 0.048 Uiso 1 1 calc GR . . . .
C14 C 0.23299(19) 0.40975(13) 0.19693(9) 0.0236(3) Uani 1 1 d . . . . .
H14A H 0.210892 0.361338 0.153108 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.157649 0.472609 0.194898 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.215310 0.369634 0.245134 0.035 Uiso 1 1 calc GR . . . .
C15 C 0.17838(19) 0.70902(13) 0.27576(9) 0.0246(3) Uani 1 1 d . . . . .
H15A H 0.068468 0.732426 0.258035 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.232690 0.769560 0.302854 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.166445 0.646699 0.310833 0.037 Uiso 1 1 calc GR . . . .
C16 C 0.4942(2) 0.80081(12) 0.07039(9) 0.0231(3) Uani 1 1 d . . . . .
H16A H 0.546545 0.759167 0.028704 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.505749 0.879246 0.060115 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.376158 0.781848 0.073352 0.035 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4280(16) . ?
O1 C7 1.3795(17) . ?
O2 C2 1.4241(17) . ?
O2 C14 1.4200(17) . ?
O3 C3 1.4233(16) . ?
O3 C15 1.4246(18) . ?
O4 C4 1.4289(16) . ?
O4 C16 1.4242(17) . ?
O5 C1 1.4044(16) . ?
O5 C5 1.4423(16) . ?
C1 H1 0.9800 . ?
C1 C2 1.5259(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.5358(19) . ?
C3 H3 0.9800 . ?
C3 C4 1.5182(18) . ?
C4 H4 0.9800 . ?
C4 C5 1.5360(18) . ?
C5 H5 0.9800 . ?
C5 C6 1.5129(19) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.4045(19) . ?
C7 C12 1.386(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.504(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C7 O1 C1 119.08(11) . . ?
C14 O2 C2 113.93(11) . . ?
C3 O3 C15 112.18(10) . . ?
C16 O4 C4 113.33(11) . . ?
C1 O5 C5 114.93(10) . . ?
O1 C1 H1 109.2 . . ?
O1 C1 C2 104.42(10) . . ?
O5 C1 O1 113.12(11) . . ?
O5 C1 H1 109.2 . . ?
O5 C1 C2 111.56(11) . . ?
C2 C1 H1 109.2 . . ?
O2 C2 C1 106.31(11) . . ?
O2 C2 H2 110.2 . . ?
O2 C2 C3 111.14(11) . . ?
C1 C2 H2 110.2 . . ?
C1 C2 C3 108.85(11) . . ?
C3 C2 H2 110.2 . . ?
O3 C3 C2 112.48(11) . . ?
O3 C3 H3 108.9 . . ?
O3 C3 C4 108.90(11) . . ?
C2 C3 H3 108.9 . . ?
C4 C3 C2 108.56(11) . . ?
C4 C3 H3 108.9 . . ?
O4 C4 C3 110.42(11) . . ?
O4 C4 H4 109.9 . . ?
O4 C4 C5 106.80(11) . . ?
C3 C4 H4 109.9 . . ?
C3 C4 C5 109.91(10) . . ?
C5 C4 H4 109.9 . . ?
O5 C5 C4 111.36(11) . . ?
O5 C5 H5 108.9 . . ?
O5 C5 C6 106.34(11) . . ?
C4 C5 H5 108.9 . . ?
C6 C5 C4 112.38(11) . . ?
C6 C5 H5 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 114.31(12) . . ?
O1 C7 C12 124.33(13) . . ?
C12 C7 C8 121.35(13) . . ?
C7 C8 C13 120.42(13) . . ?
C9 C8 C7 117.64(14) . . ?
C9 C8 C13 121.92(13) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.65(14) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.66(14) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.27(14) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 119.42(13) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_date_sample_data_collection 2019-10-24
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.904
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2059248'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
(2?,4?-dichlorophenyl)-2,3,4-tri-O-methyl-α-L-rhamnopyranoside
_chemical_formula_moiety         'C15 H20 Cl2 O5'
_chemical_formula_sum            'C15 H20 Cl2 O5'
_chemical_formula_weight         351.21
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H20Cl2O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2374(2)
_cell_length_b                   12.4665(2)
_cell_length_c                   13.7074(3)
_cell_angle_alpha                64.328(2)
_cell_angle_beta                 88.439(2)
_cell_angle_gamma                86.714(2)
_cell_volume                     1266.59(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    20368
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      71.6410
_cell_measurement_theta_min      3.5650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.638
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -7 -4 0.1039
-3 0 -7 0.0932
1 8 4 0.0961
-3 7 4 0.0862
-3 -1 6 0.1080
3 -7 -4 0.1222
3 1 -6 0.0930
0 0 8 0.0554
5 2 4 0.1498
0 0 -8 0.0384

_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.1
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.8154 -7.1081 -3.6410 0.5669 -0.5354 0.6261
-2.9988 0.0010 -7.0007 -0.6468 -0.6076 0.5363
1.2649 7.9509 4.1505 -0.6797 0.6430 -0.3530
-2.5611 6.8535 3.7285 -0.6743 0.6397 0.3689
-3.0010 -1.0015 5.9967 0.5327 0.5946 0.5832
2.6293 -6.7903 -3.6979 0.6703 -0.6360 -0.3825
3.0010 1.0015 -5.9967 -0.5327 -0.5946 -0.5832
0.2834 -0.3748 7.8209 0.6874 0.7257 -0.0280
4.9993 1.9999 4.0032 0.1964 0.3521 -0.9445
-0.0835 -0.1253 -7.5210 -0.5918 -0.7182 -0.0000

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24899
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.758
_diffrn_reflns_theta_min         3.578
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -7.00   1.00    1.00    --   20.00 126.00 134.42   27
  2  ω   -108.00  -7.00   1.00    1.00    --  -36.45 -19.00 -60.00  101
  3  ω   -109.00 -39.00   1.00    1.00    --  -36.45-178.00 -90.00   70
  4  ω   -109.00 -39.00   1.00    1.00    --  -36.45-178.00 120.00   70
  5  ω    -55.00  33.00   1.00    1.00    --  -36.45  38.00 120.00   88
  6  ω   -109.00 -39.00   1.00    1.00    --  -36.45-178.00-180.00   70
  7  ω     30.00  94.00   1.00    1.00    --   36.45-132.00-164.00   64
  8  ω     18.00 106.00   1.00    1.00    --   36.45  38.00  90.00   88
  9  ω     34.00  97.00   1.00    1.00    --   36.45-137.00  18.00   63
 10  ω      4.00  30.00   1.00    1.00    --   36.45  88.00 -23.83   26
 11  ω      4.00  30.00   1.00    1.00    --   36.45  88.00-130.28   26
 12  ω      2.00  29.00   1.00    1.00    --   36.45  90.00 155.17   27
 13  ω      2.00  29.00   1.00    1.00    --   36.45  90.00  85.72   27
 14  ω     15.00  42.00   1.00    1.00    --   44.00  81.00 -19.70   27
 15  ω     15.00  42.00   1.00    1.00    --   44.00  81.00  56.21   27
 16  ω     16.00  42.00   1.00    1.00    --   44.00  80.00 170.68   26
 17  ω     25.00 115.00   1.00    1.00    --   48.00  71.00  24.39   90
 18  ω     27.00 119.00   1.00    1.00    --   52.00  73.00 -88.07   92
 19  ω     27.00 119.00   1.00    1.00    --   52.00  74.00-135.97   92
 20  ω     28.00 119.00   1.00    1.00    --   52.00  72.00 134.12   91
 21  ω     27.00 119.00   1.00    1.00    --   52.00  74.00 166.70   92
 22  ω     31.00 123.00   1.00    1.00    --   56.00  74.00 -39.49   92
 23  ω     31.00 123.00   1.00    1.00    --   56.00  73.00  80.92   92
 24  ω     90.00 175.00   1.00    1.00    --  107.73  61.00-180.00   85
 25  ω     90.00 175.00   1.00    1.00    --  107.73  61.00 -60.00   85
 26  ω     90.00 175.00   1.00    1.00    --  107.73  61.00 120.00   85
 27  ω     90.00 175.00   1.00    1.00    --  107.73  61.00 -90.00   85
 28  ω     38.00 108.00   1.00    1.00    --  107.73-111.00 -90.00   70
 29  ω     90.00 175.00   1.00    1.00    --  107.73  61.00 -30.00   85
 30  ω     40.00 134.00   1.00    1.00    --  107.73 -77.00 -90.00   94
 31  ω     90.00 175.00   1.00    1.00    --  107.73  61.00 150.00   85
 32  ω     90.00 176.00   1.00    1.00    --  107.73  45.00 120.00   86
 33  ω     90.00 176.00   1.00    1.00    --  107.73  45.00  60.00   86
 34  ω     90.00 176.00   1.00    1.00    --  107.73  45.00 -30.00   86
 35  ω     90.00 176.00   1.00    1.00    --  107.73  45.00 -90.00   86
 36  ω     61.00 146.00   1.00    1.00    --  107.73 178.00 -60.00   85
 37  ω     38.00 107.00   1.00    1.00    --  107.73 -94.00 -30.00   69
 38  ω     90.00 176.00   1.00    1.00    --  107.73  45.00 150.00   86
 39  ω     90.00 176.00   1.00    1.00    --  107.73  45.00-180.00   86
 40  ω     90.00 176.00   1.00    1.00    --  107.73  45.00-150.00   86
 41  ω     90.00 176.00   1.00    1.00    --  107.73  45.00  30.00   86
 42  ω     90.00 176.00   1.00    1.00    --  107.73  45.00  90.00   86
 43  ω     41.00 126.00   1.00    1.00    --  107.73 -61.00  60.00   85
 44  ω     90.00 175.00   1.00    1.00    --  107.73  61.00-150.00   85
 45  ω     90.00 176.00   1.00    1.00    --  107.73  45.00 -60.00   86
 46  ω     90.00 175.00   1.00    1.00    --  107.73  61.00-120.00   85
 47  ω     90.00 176.00   1.00    1.00    --  107.73  45.00   0.00   86
 48  ω     90.00 175.00   1.00    1.00    --  107.73  61.00  90.00   85
 49  ω     90.00 175.00   1.00    1.00    --  107.73  61.00  30.00   85
 50  ω     90.00 176.00   1.00    1.00    --  107.73  45.00-120.00   86
 51  ω    133.00 171.00   1.00    1.00    --  107.73  61.00  60.00   38
 52  ω     48.00 108.00   1.00    1.00    --  107.73-111.00  90.00   60
 53  ω     91.00 119.00   1.00    1.00    --  107.73  61.00   0.00   28
 54  ω     90.00 118.00   1.00    1.00    --  107.73  61.00  60.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0275344000
_diffrn_orient_matrix_UB_12      -0.1319286000
_diffrn_orient_matrix_UB_13      0.0805770000
_diffrn_orient_matrix_UB_21      -0.0194837000
_diffrn_orient_matrix_UB_22      0.0343048000
_diffrn_orient_matrix_UB_23      0.0951401000
_diffrn_orient_matrix_UB_31      -0.1842669000
_diffrn_orient_matrix_UB_32      -0.0162896000
_diffrn_orient_matrix_UB_33      0.0023201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.780
_reflns_Friedel_fraction_max     0.756
_reflns_number_gt                8570
_reflns_number_total             8630
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     607
_refine_ls_number_reflns         8630
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+0.2859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0574
_refine_special_details          'Refined without restraint'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C1C(H1C), C2C(H2C), C3C(H3C),
 C4C(H4C), C5C(H5C), C1B(H1B), C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C9C(H9C), C11C(H11C), C12C(H12C), C9B(H9B),
 C11B(H11B), C12B(H12B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C6C(H6CA,H6CB,H6CC), C13C(H13D,H13E,H13F), C14C(H14D,H14E,H14F),
 C15C(H15D,H15E,H15F), C6B(H6BA,H6BB,H6BC), C13B(H13G,H13H,H13I), C14B(H14G,
 H14H,H14I), C15B(H15G,H15H,H15I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.02926(7) 0.79322(4) 1.01986(4) 0.02380(12) Uani 1 1 d . . . . .
Cl2 Cl 0.10431(8) 1.22646(5) 1.00469(4) 0.02768(13) Uani 1 1 d . . . . .
O1 O 0.2511(2) 0.86689(12) 0.84009(11) 0.0171(3) Uani 1 1 d . . . . .
O2 O 0.5386(2) 0.80168(14) 0.66995(13) 0.0225(3) Uani 1 1 d . . . . .
O3 O 0.3438(2) 0.60993(13) 0.71032(12) 0.0206(3) Uani 1 1 d . . . . .
O4 O 0.0492(2) 0.74249(16) 0.60519(14) 0.0267(4) Uani 1 1 d . . . . .
O5 O 0.2614(2) 0.96385(13) 0.65152(11) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.3494(3) 0.89354(19) 0.74559(16) 0.0172(4) Uani 1 1 d . . . . .
H1 H 0.442172 0.937424 0.749323 0.021 Uiso 1 1 calc R . . . .
C2 C 0.4129(3) 0.77405(18) 0.74942(16) 0.0170(4) Uani 1 1 d . . . . .
H2 H 0.457971 0.723046 0.821177 0.020 Uiso 1 1 calc R . . . .
C3 C 0.2785(3) 0.71103(18) 0.72360(17) 0.0175(4) Uani 1 1 d . . . . .
H3 H 0.200547 0.684396 0.783723 0.021 Uiso 1 1 calc R . . . .
C4 C 0.1893(3) 0.7942(2) 0.62049(17) 0.0188(4) Uani 1 1 d . . . . .
H4 H 0.262190 0.815221 0.557881 0.023 Uiso 1 1 calc R . . . .
C5 C 0.1276(3) 0.90672(19) 0.63204(17) 0.0200(5) Uani 1 1 d . . . . .
H5 H 0.051857 0.884182 0.693305 0.024 Uiso 1 1 calc R . . . .
C6 C 0.0441(4) 0.9995(2) 0.5320(2) 0.0309(6) Uani 1 1 d . . . . .
H6A H 0.003481 1.065462 0.545721 0.046 Uiso 1 1 calc GR . . . .
H6B H -0.044755 0.965245 0.513530 0.046 Uiso 1 1 calc GR . . . .
H6C H 0.120306 1.026969 0.473051 0.046 Uiso 1 1 calc GR . . . .
C7 C 0.2197(3) 0.95686(18) 0.87183(16) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.1174(3) 0.93020(18) 0.96128(16) 0.0170(4) Uani 1 1 d . . . . .
C9 C 0.0806(3) 1.0125(2) 1.00234(17) 0.0194(5) Uani 1 1 d . . . . .
H9 H 0.012497 0.993948 1.062073 0.023 Uiso 1 1 calc R . . . .
C10 C 0.1474(3) 1.12290(19) 0.95268(17) 0.0195(5) Uani 1 1 d . . . . .
C11 C 0.2460(3) 1.15267(19) 0.86239(18) 0.0213(5) Uani 1 1 d . . . . .
H11 H 0.288104 1.227839 0.829001 0.026 Uiso 1 1 calc R . . . .
C12 C 0.2817(3) 1.06893(19) 0.82190(17) 0.0198(5) Uani 1 1 d . . . . .
H12 H 0.347551 1.088458 0.760990 0.024 Uiso 1 1 calc R . . . .
C13 C 0.6854(4) 0.7324(3) 0.7100(2) 0.0408(7) Uani 1 1 d . . . . .
H13A H 0.767430 0.758520 0.654634 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.667183 0.649963 0.730570 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.720899 0.741715 0.771879 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.3568(4) 0.5046(2) 0.8090(2) 0.0334(6) Uani 1 1 d . . . . .
H14A H 0.410392 0.441648 0.795836 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.250037 0.481837 0.837726 0.050 Uiso 1 1 calc GR . . . .
H14C H 0.418619 0.519093 0.860023 0.050 Uiso 1 1 calc GR . . . .
C15 C 0.0747(3) 0.6714(2) 0.5476(2) 0.0299(6) Uani 1 1 d . . . . .
H15A H 0.135512 0.714271 0.482728 0.045 Uiso 1 1 calc GR . . . .
H15B H -0.028457 0.653271 0.528932 0.045 Uiso 1 1 calc GR . . . .
H15C H 0.134157 0.598600 0.592210 0.045 Uiso 1 1 calc GR . . . .
Cl1C Cl 0.65634(9) 0.12131(6) -0.01201(5) 0.03566(15) Uani 1 1 d . . . . .
Cl2C Cl 0.28513(8) -0.22618(6) 0.25791(5) 0.03594(15) Uani 1 1 d . . . . .
O1C O 0.5652(2) 0.24050(14) 0.12146(12) 0.0267(4) Uani 1 1 d . . . . .
O2C O 0.8345(3) 0.37041(15) 0.24041(15) 0.0332(5) Uani 1 1 d . . . . .
O3C O 0.8410(2) 0.54994(15) 0.03255(15) 0.0306(4) Uani 1 1 d . . . . .
O4C O 0.5156(2) 0.63654(14) 0.01494(13) 0.0289(4) Uani 1 1 d . . . . .
O5C O 0.4842(2) 0.33603(14) 0.23049(13) 0.0280(4) Uani 1 1 d . . . . .
C1C C 0.6124(3) 0.2757(2) 0.20264(17) 0.0247(5) Uani 1 1 d . . . . .
H1C H 0.644264 0.203639 0.267541 0.030 Uiso 1 1 calc R . . . .
C2C C 0.7620(3) 0.3484(2) 0.15866(18) 0.0255(5) Uani 1 1 d . . . . .
H2C H 0.840811 0.305481 0.131852 0.031 Uiso 1 1 calc R . . . .
C3C C 0.7133(3) 0.4700(2) 0.06674(18) 0.0242(5) Uani 1 1 d . . . . .
H3C H 0.677359 0.457983 0.004805 0.029 Uiso 1 1 calc R . . . .
C4C C 0.5736(3) 0.5292(2) 0.10326(18) 0.0240(5) Uani 1 1 d . . . . .
H4C H 0.611305 0.547840 0.161100 0.029 Uiso 1 1 calc R . . . .
C5C C 0.4307(3) 0.4489(2) 0.14434(19) 0.0279(5) Uani 1 1 d . . . . .
H5C H 0.386749 0.435674 0.084951 0.034 Uiso 1 1 calc R . . . .
C6C C 0.2969(4) 0.5003(2) 0.1919(2) 0.0402(7) Uani 1 1 d . . . . .
H6CA H 0.209102 0.447311 0.215857 0.060 Uiso 1 1 calc GR . . . .
H6CB H 0.258063 0.576460 0.137846 0.060 Uiso 1 1 calc GR . . . .
H6CC H 0.338786 0.509751 0.252285 0.060 Uiso 1 1 calc GR . . . .
C7C C 0.4930(3) 0.1339(2) 0.15665(18) 0.0232(5) Uani 1 1 d . . . . .
C8C C 0.5269(3) 0.0673(2) 0.09830(18) 0.0250(5) Uani 1 1 d . . . . .
C9C C 0.4619(3) -0.0423(2) 0.1289(2) 0.0277(5) Uani 1 1 d . . . . .
H9C H 0.484339 -0.085799 0.089142 0.033 Uiso 1 1 calc R . . . .
C10C C 0.3631(3) -0.0865(2) 0.2192(2) 0.0268(5) Uani 1 1 d . . . . .
C11C C 0.3246(3) -0.0218(2) 0.27687(19) 0.0274(5) Uani 1 1 d . . . . .
H11C H 0.255255 -0.051614 0.336295 0.033 Uiso 1 1 calc R . . . .
C12C C 0.3904(3) 0.0886(2) 0.24567(19) 0.0271(5) Uani 1 1 d . . . . .
H12C H 0.365288 0.132517 0.284799 0.032 Uiso 1 1 calc R . . . .
C13C C 0.9412(4) 0.2778(2) 0.3088(2) 0.0329(6) Uani 1 1 d . . . . .
H13D H 1.022788 0.259791 0.265960 0.049 Uiso 1 1 calc GR . . . .
H13E H 0.881400 0.208218 0.349554 0.049 Uiso 1 1 calc GR . . . .
H13F H 0.992415 0.302130 0.357509 0.049 Uiso 1 1 calc GR . . . .
C14C C 0.9701(4) 0.5173(3) -0.0194(2) 0.0383(7) Uani 1 1 d . . . . .
H14D H 0.928282 0.500665 -0.075838 0.057 Uiso 1 1 calc GR . . . .
H14E H 1.028014 0.447537 0.032105 0.057 Uiso 1 1 calc GR . . . .
H14F H 1.042569 0.581446 -0.050186 0.057 Uiso 1 1 calc GR . . . .
C15C C 0.5753(5) 0.7408(2) 0.0128(3) 0.0438(8) Uani 1 1 d . . . . .
H15D H 0.514420 0.808954 -0.038534 0.066 Uiso 1 1 calc GR . . . .
H15E H 0.687911 0.745647 -0.007975 0.066 Uiso 1 1 calc GR . . . .
H15F H 0.564550 0.738949 0.083383 0.066 Uiso 1 1 calc GR . . . .
Cl1B Cl 0.86053(7) 0.58240(4) 0.28207(4) 0.02498(13) Uani 1 1 d . . . . .
Cl2B Cl 0.87059(7) 1.01459(4) 0.27660(4) 0.02589(13) Uani 1 1 d . . . . .
O1B O 0.6197(2) 0.53546(13) 0.44591(12) 0.0206(3) Uani 1 1 d . . . . .
O2B O 0.3302(2) 0.33662(15) 0.61889(13) 0.0252(4) Uani 1 1 d . . . . .
O3B O 0.5305(2) 0.16492(13) 0.58920(12) 0.0210(3) Uani 1 1 d . . . . .
O4B O 0.8276(2) 0.18515(15) 0.68558(15) 0.0283(4) Uani 1 1 d . . . . .
O5B O 0.6058(2) 0.46545(13) 0.63396(12) 0.0201(3) Uani 1 1 d . . . . .
C1B C 0.5201(3) 0.48663(19) 0.54047(17) 0.0203(5) Uani 1 1 d . . . . .
H1B H 0.427593 0.542682 0.532937 0.024 Uiso 1 1 calc R . . . .
C2B C 0.4574(3) 0.37347(19) 0.54081(17) 0.0207(5) Uani 1 1 d . . . . .
H2B H 0.414180 0.391340 0.469214 0.025 Uiso 1 1 calc R . . . .
C3B C 0.5941(3) 0.27649(19) 0.56971(17) 0.0186(4) Uani 1 1 d . . . . .
H3B H 0.670812 0.298917 0.508996 0.022 Uiso 1 1 calc R . . . .
C4B C 0.6848(3) 0.26113(19) 0.67022(18) 0.0192(4) Uani 1 1 d . . . . .
H4B H 0.613885 0.227959 0.733845 0.023 Uiso 1 1 calc R . . . .
C5B C 0.7431(3) 0.38141(19) 0.65625(18) 0.0208(5) Uani 1 1 d . . . . .
H5B H 0.819241 0.411011 0.595218 0.025 Uiso 1 1 calc R . . . .
C6B C 0.8237(3) 0.3769(2) 0.7554(2) 0.0287(5) Uani 1 1 d . . . . .
H6BA H 0.865853 0.453081 0.739073 0.043 Uiso 1 1 calc GR . . . .
H6BB H 0.911182 0.317076 0.777196 0.043 Uiso 1 1 calc GR . . . .
H6BC H 0.745599 0.357727 0.812984 0.043 Uiso 1 1 calc GR . . . .
C7B C 0.6742(3) 0.64710(19) 0.41472(17) 0.0175(4) Uani 1 1 d . . . . .
C8B C 0.7887(3) 0.68221(18) 0.33156(16) 0.0174(4) Uani 1 1 d . . . . .
C9B C 0.8472(3) 0.7956(2) 0.28839(18) 0.0187(4) Uani 1 1 d . . . . .
H9B H 0.921449 0.819221 0.231504 0.022 Uiso 1 1 calc R . . . .
C10B C 0.7927(3) 0.87302(19) 0.33169(18) 0.0194(5) Uani 1 1 d . . . . .
C11B C 0.6835(3) 0.8394(2) 0.41624(18) 0.0220(5) Uani 1 1 d . . . . .
H11B H 0.649673 0.892240 0.445041 0.026 Uiso 1 1 calc R . . . .
C12B C 0.6242(3) 0.7257(2) 0.45826(18) 0.0202(5) Uani 1 1 d . . . . .
H12B H 0.550748 0.702203 0.515641 0.024 Uiso 1 1 calc R . . . .
C13B C 0.1878(3) 0.3084(3) 0.5799(2) 0.0378(7) Uani 1 1 d . . . . .
H13G H 0.146986 0.377383 0.518132 0.057 Uiso 1 1 calc GR . . . .
H13H H 0.106550 0.284015 0.635858 0.057 Uiso 1 1 calc GR . . . .
H13I H 0.213998 0.244818 0.559594 0.057 Uiso 1 1 calc GR . . . .
C14B C 0.5320(4) 0.1415(2) 0.49661(19) 0.0292(6) Uani 1 1 d . . . . .
H14G H 0.469245 0.203404 0.440007 0.044 Uiso 1 1 calc GR . . . .
H14H H 0.485673 0.066203 0.514927 0.044 Uiso 1 1 calc GR . . . .
H14I H 0.641926 0.139134 0.472301 0.044 Uiso 1 1 calc GR . . . .
C15B C 0.8074(4) 0.0619(2) 0.7502(2) 0.0331(6) Uani 1 1 d . . . . .
H15G H 0.747576 0.030202 0.710349 0.050 Uiso 1 1 calc GR . . . .
H15H H 0.748720 0.051445 0.814987 0.050 Uiso 1 1 calc GR . . . .
H15I H 0.912092 0.020637 0.769127 0.050 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.735(2) . ?
Cl2 C10 1.741(2) . ?
O1 C1 1.430(2) . ?
O1 C7 1.378(2) . ?
O2 C2 1.425(3) . ?
O2 C13 1.420(3) . ?
O3 C3 1.424(2) . ?
O3 C14 1.420(3) . ?
O4 C4 1.417(3) . ?
O4 C15 1.425(3) . ?
O5 C1 1.398(3) . ?
O5 C5 1.437(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.530(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.527(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.520(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.536(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.510(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.395(3) . ?
C7 C12 1.384(3) . ?
C8 C9 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(3) . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Cl1C C8C 1.729(2) . ?
Cl2C C10C 1.743(3) . ?
O1C C1C 1.431(3) . ?
O1C C7C 1.368(3) . ?
O2C C2C 1.417(3) . ?
O2C C13C 1.406(3) . ?
O3C C3C 1.417(3) . ?
O3C C14C 1.402(3) . ?
O4C C4C 1.428(3) . ?
O4C C15C 1.404(3) . ?
O5C C1C 1.401(3) . ?
O5C C5C 1.445(3) . ?
C1C H1C 0.9800 . ?
C1C C2C 1.523(4) . ?
C2C H2C 0.9800 . ?
C2C C3C 1.533(3) . ?
C3C H3C 0.9800 . ?
C3C C4C 1.520(3) . ?
C4C H4C 0.9800 . ?
C4C C5C 1.522(4) . ?
C5C H5C 0.9800 . ?
C5C C6C 1.514(4) . ?
C6C H6CA 0.9600 . ?
C6C H6CB 0.9600 . ?
C6C H6CC 0.9600 . ?
C7C C8C 1.394(3) . ?
C7C C12C 1.387(4) . ?
C8C C9C 1.379(4) . ?
C9C H9C 0.9300 . ?
C9C C10C 1.380(4) . ?
C10C C11C 1.372(4) . ?
C11C H11C 0.9300 . ?
C11C C12C 1.391(4) . ?
C12C H12C 0.9300 . ?
C13C H13D 0.9600 . ?
C13C H13E 0.9600 . ?
C13C H13F 0.9600 . ?
C14C H14D 0.9600 . ?
C14C H14E 0.9600 . ?
C14C H14F 0.9600 . ?
C15C H15D 0.9600 . ?
C15C H15E 0.9600 . ?
C15C H15F 0.9600 . ?
Cl1B C8B 1.727(2) . ?
Cl2B C10B 1.745(2) . ?
O1B C1B 1.428(3) . ?
O1B C7B 1.367(3) . ?
O2B C2B 1.423(3) . ?
O2B C13B 1.424(3) . ?
O3B C3B 1.426(3) . ?
O3B C14B 1.420(3) . ?
O4B C4B 1.428(3) . ?
O4B C15B 1.420(3) . ?
O5B C1B 1.395(3) . ?
O5B C5B 1.440(3) . ?
C1B H1B 0.9800 . ?
C1B C2B 1.528(3) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.529(3) . ?
C3B H3B 0.9800 . ?
C3B C4B 1.518(3) . ?
C4B H4B 0.9800 . ?
C4B C5B 1.531(3) . ?
C5B H5B 0.9800 . ?
C5B C6B 1.507(3) . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7B C8B 1.391(3) . ?
C7B C12B 1.391(3) . ?
C8B C9B 1.385(3) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.385(3) . ?
C10B C11B 1.376(3) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.392(3) . ?
C12B H12B 0.9300 . ?
C13B H13G 0.9600 . ?
C13B H13H 0.9600 . ?
C13B H13I 0.9600 . ?
C14B H14G 0.9600 . ?
C14B H14H 0.9600 . ?
C14B H14I 0.9600 . ?
C15B H15G 0.9600 . ?
C15B H15H 0.9600 . ?
C15B H15I 0.9600 . ?

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
C7 O1 C1 117.24(16) . . ?
C13 O2 C2 113.23(18) . . ?
C14 O3 C3 113.39(16) . . ?
C4 O4 C15 115.56(18) . . ?
C1 O5 C5 114.52(16) . . ?
O1 C1 H1 108.7 . . ?
O1 C1 C2 106.68(16) . . ?
O5 C1 O1 111.14(18) . . ?
O5 C1 H1 108.7 . . ?
O5 C1 C2 112.89(17) . . ?
C2 C1 H1 108.7 . . ?
O2 C2 C1 105.70(17) . . ?
O2 C2 H2 109.8 . . ?
O2 C2 C3 110.42(17) . . ?
C1 C2 H2 109.8 . . ?
C3 C2 C1 111.27(18) . . ?
C3 C2 H2 109.8 . . ?
O3 C3 C2 110.75(18) . . ?
O3 C3 H3 108.8 . . ?
O3 C3 C4 108.50(17) . . ?
C2 C3 H3 108.8 . . ?
C4 C3 C2 111.17(18) . . ?
C4 C3 H3 108.8 . . ?
O4 C4 C3 111.33(18) . . ?
O4 C4 H4 110.3 . . ?
O4 C4 C5 105.95(18) . . ?
C3 C4 H4 110.3 . . ?
C3 C4 C5 108.58(17) . . ?
C5 C4 H4 110.3 . . ?
O5 C5 C4 110.16(18) . . ?
O5 C5 H5 109.0 . . ?
O5 C5 C6 105.81(19) . . ?
C4 C5 H5 109.0 . . ?
C6 C5 C4 113.63(18) . . ?
C6 C5 H5 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 116.06(18) . . ?
O1 C7 C12 124.89(19) . . ?
C12 C7 C8 119.06(19) . . ?
C7 C8 Cl1 119.57(16) . . ?
C9 C8 Cl1 119.17(17) . . ?
C9 C8 C7 121.2(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 Cl2 119.07(17) . . ?
C11 C10 Cl2 119.60(18) . . ?
C11 C10 C9 121.3(2) . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(2) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.4(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7C O1C C1C 116.84(17) . . ?
C13C O2C C2C 114.49(19) . . ?
C14C O3C C3C 114.54(19) . . ?
C15C O4C C4C 114.4(2) . . ?
C1C O5C C5C 114.73(17) . . ?
O1C C1C H1C 108.2 . . ?
O1C C1C C2C 106.28(18) . . ?
O5C C1C O1C 111.7(2) . . ?
O5C C1C H1C 108.2 . . ?
O5C C1C C2C 113.98(19) . . ?
C2C C1C H1C 108.2 . . ?
O2C C2C C1C 110.49(19) . . ?
O2C C2C H2C 109.7 . . ?
O2C C2C C3C 107.05(18) . . ?
C1C C2C H2C 109.7 . . ?
C1C C2C C3C 110.0(2) . . ?
C3C C2C H2C 109.7 . . ?
O3C C3C C2C 113.5(2) . . ?
O3C C3C H3C 108.7 . . ?
O3C C3C C4C 107.18(19) . . ?
C2C C3C H3C 108.7 . . ?
C4C C3C C2C 109.88(19) . . ?
C4C C3C H3C 108.7 . . ?
O4C C4C C3C 110.42(19) . . ?
O4C C4C H4C 109.3 . . ?
O4C C4C C5C 107.1(2) . . ?
C3C C4C H4C 109.3 . . ?
C3C C4C C5C 111.42(19) . . ?
C5C C4C H4C 109.3 . . ?
O5C C5C C4C 109.6(2) . . ?
O5C C5C H5C 109.5 . . ?
O5C C5C C6C 106.18(19) . . ?
C4C C5C H5C 109.5 . . ?
C6C C5C C4C 112.4(2) . . ?
C6C C5C H5C 109.5 . . ?
C5C C6C H6CA 109.5 . . ?
C5C C6C H6CB 109.5 . . ?
C5C C6C H6CC 109.5 . . ?
H6CA C6C H6CB 109.5 . . ?
H6CA C6C H6CC 109.5 . . ?
H6CB C6C H6CC 109.5 . . ?
O1C C7C C8C 116.9(2) . . ?
O1C C7C C12C 124.4(2) . . ?
C12C C7C C8C 118.7(2) . . ?
C7C C8C Cl1C 119.4(2) . . ?
C9C C8C Cl1C 119.62(18) . . ?
C9C C8C C7C 121.0(2) . . ?
C8C C9C H9C 120.4 . . ?
C8C C9C C10C 119.2(2) . . ?
C10C C9C H9C 120.4 . . ?
C9C C10C Cl2C 118.5(2) . . ?
C11C C10C Cl2C 120.4(2) . . ?
C11C C10C C9C 121.2(2) . . ?
C10C C11C H11C 120.3 . . ?
C10C C11C C12C 119.4(2) . . ?
C12C C11C H11C 120.3 . . ?
C7C C12C C11C 120.5(2) . . ?
C7C C12C H12C 119.7 . . ?
C11C C12C H12C 119.7 . . ?
O2C C13C H13D 109.5 . . ?
O2C C13C H13E 109.5 . . ?
O2C C13C H13F 109.5 . . ?
H13D C13C H13E 109.5 . . ?
H13D C13C H13F 109.5 . . ?
H13E C13C H13F 109.5 . . ?
O3C C14C H14D 109.5 . . ?
O3C C14C H14E 109.5 . . ?
O3C C14C H14F 109.5 . . ?
H14D C14C H14E 109.5 . . ?
H14D C14C H14F 109.5 . . ?
H14E C14C H14F 109.5 . . ?
O4C C15C H15D 109.5 . . ?
O4C C15C H15E 109.5 . . ?
O4C C15C H15F 109.5 . . ?
H15D C15C H15E 109.5 . . ?
H15D C15C H15F 109.5 . . ?
H15E C15C H15F 109.5 . . ?
C7B O1B C1B 118.52(17) . . ?
C2B O2B C13B 113.14(19) . . ?
C14B O3B C3B 113.81(17) . . ?
C15B O4B C4B 115.6(2) . . ?
C1B O5B C5B 114.58(16) . . ?
O1B C1B H1B 109.0 . . ?
O1B C1B C2B 104.90(17) . . ?
O5B C1B O1B 111.83(19) . . ?
O5B C1B H1B 109.0 . . ?
O5B C1B C2B 113.13(17) . . ?
C2B C1B H1B 109.0 . . ?
O2B C2B C1B 106.64(18) . . ?
O2B C2B H2B 109.6 . . ?
O2B C2B C3B 110.89(17) . . ?
C1B C2B H2B 109.6 . . ?
C1B C2B C3B 110.6(2) . . ?
C3B C2B H2B 109.6 . . ?
O3B C3B C2B 110.64(19) . . ?
O3B C3B H3B 108.8 . . ?
O3B C3B C4B 108.23(17) . . ?
C2B C3B H3B 108.8 . . ?
C4B C3B C2B 111.48(18) . . ?
C4B C3B H3B 108.8 . . ?
O4B C4B C3B 110.61(18) . . ?
O4B C4B H4B 110.0 . . ?
O4B C4B C5B 106.19(19) . . ?
C3B C4B H4B 110.0 . . ?
C3B C4B C5B 109.92(17) . . ?
C5B C4B H4B 110.0 . . ?
O5B C5B C4B 109.48(19) . . ?
O5B C5B H5B 109.1 . . ?
O5B C5B C6B 106.19(18) . . ?
C4B C5B H5B 109.1 . . ?
C6B C5B C4B 113.83(19) . . ?
C6B C5B H5B 109.1 . . ?
C5B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C5B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
O1B C7B C8B 115.34(19) . . ?
O1B C7B C12B 125.6(2) . . ?
C12B C7B C8B 119.1(2) . . ?
C7B C8B Cl1B 119.51(17) . . ?
C9B C8B Cl1B 119.38(17) . . ?
C9B C8B C7B 121.1(2) . . ?
C8B C9B H9B 120.7 . . ?
C8B C9B C10B 118.6(2) . . ?
C10B C9B H9B 120.7 . . ?
C9B C10B Cl2B 117.50(18) . . ?
C11B C10B Cl2B 120.96(17) . . ?
C11B C10B C9B 121.5(2) . . ?
C10B C11B H11B 120.3 . . ?
C10B C11B C12B 119.4(2) . . ?
C12B C11B H11B 120.3 . . ?
C7B C12B C11B 120.2(2) . . ?
C7B C12B H12B 119.9 . . ?
C11B C12B H12B 119.9 . . ?
O2B C13B H13G 109.5 . . ?
O2B C13B H13H 109.5 . . ?
O2B C13B H13I 109.5 . . ?
H13G C13B H13H 109.5 . . ?
H13G C13B H13I 109.5 . . ?
H13H C13B H13I 109.5 . . ?
O3B C14B H14G 109.5 . . ?
O3B C14B H14H 109.5 . . ?
O3B C14B H14I 109.5 . . ?
H14G C14B H14H 109.5 . . ?
H14G C14B H14I 109.5 . . ?
H14H C14B H14I 109.5 . . ?
O4B C15B H15G 109.5 . . ?
O4B C15B H15H 109.5 . . ?
O4B C15B H15I 109.5 . . ?
H15G C15B H15H 109.5 . . ?
H15G C15B H15I 109.5 . . ?
H15H C15B H15I 109.5 . . ?

_olex2_date_sample_data_collection 2020-03-11
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.285
_oxdiff_exptl_absorpt_empirical_full_min 0.887
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2059250'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
(2?-methylphenyl)-6-O-triisopropylsilyl-2,3,4-tri-O-methyl-α-D-mannopyranoside
_chemical_formula_moiety         'C25 H44 O6 Si'
_chemical_formula_sum            'C25 H44 O6 Si'
_chemical_formula_weight         468.69
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H44O6Si
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7564(2)
_cell_length_b                   13.7188(4)
_cell_length_c                   25.4041(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.463(3)
_cell_angle_gamma                90
_cell_volume                     2680.33(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15510
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9350
_cell_measurement_theta_min      3.6130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -9 -1 0.0653
-3 -6 -7 0.0891
-5 0 -1 0.1097
0 -6 12 0.1116
1 1 -16 0.0879
-3 7 8 0.0728
2 -2 13 0.1055
5 3 1 0.0957

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.223
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1121 -8.8880 -0.9476 -0.0759 0.9512 0.2992
-2.7693 -6.0654 -6.7159 -0.1639 0.8835 -0.4389
-4.9060 -0.4644 -1.4797 0.2998 0.3897 -0.8708
-0.1503 -6.0349 12.0775 0.6262 0.5364 0.5658
0.8583 0.6294 -16.4324 -0.9320 0.0242 -0.3617
-2.6123 6.7218 7.6843 0.6342 -0.6019 -0.4852
2.3718 -2.4832 12.6698 0.4760 -0.0110 0.8794
4.6068 3.3152 0.5672 -0.3138 -0.6615 0.6812

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25888
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.545
_diffrn_reflns_theta_min         3.509
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -43.00   1.00    1.00    --  -38.88 -57.00-150.00   60
  2  ω   -102.00 -51.00   1.00    1.00    --  -38.88 -57.00  30.00   51
  3  ω    -42.00 -15.00   1.00    1.00    --  -38.88  38.00-150.00   27
  4  ω    -88.00 -63.00   1.00    1.00    --  -38.88 -57.00 -90.00   25
  5  ω    -26.00   2.00   1.00    1.00    --   38.88 -57.00  30.00   28
  6  ω     -7.00  20.00   1.00    1.00    --   38.88 -57.00   0.00   27
  7  ω     24.00  51.00   1.00    1.00    --   38.88-125.00 -60.00   27
  8  ω     64.00  90.00   1.00    1.00    --   38.88  77.00 -60.00   26
  9  ω     51.00  78.00   1.00    1.00    --   38.88  38.00  30.00   27
 10  ω    -10.00  17.00   1.00    1.00    --   38.88 -38.00-180.00   27
 11  ω    -28.00  18.00   1.00    1.00    --   38.88 -77.00 120.00   46
 12  ω      6.00  31.00   1.00    1.00    --   38.88  88.00 -41.51   25
 13  ω     -5.00  22.00   1.00    1.00    --   38.88 -57.00 -90.00   27
 14  ω     25.00  50.00   1.00    1.00    --   38.88-125.00  90.00   25
 15  ω     14.00  71.00   1.00    1.00    --   38.88 -99.00 120.00   57
 16  ω     84.00 109.00   1.00    1.00    --   38.88  19.00 -30.00   25
 17  ω     33.00  59.00   1.00    1.00    --   38.88 -19.00 120.00   26
 18  ω     11.00  49.00   1.00    1.00    --   38.88  19.00  30.00   38
 19  ω    -14.00  27.00   1.00    1.00    --   38.88 -38.00 -60.00   41
 20  ω     13.00  40.00   1.00    1.00    --   38.88 -77.00 150.00   27
 21  ω     22.00  53.00   1.00    1.00    --   38.88 -57.00  90.00   31
 22  ω    -10.00  17.00   1.00    1.00    --   38.88 -38.00 -90.00   27
 23  ω     62.00 102.00   1.00    1.00    --   38.88  19.00 120.00   40
 24  ω     51.00  77.00   1.00    1.00    --   38.88 -99.00   0.00   26
 25  ω     41.00  87.00   1.00    1.00    --   38.88-125.00 -30.00   46
 26  ω     30.00  78.00   1.00    1.00    --   38.88 -99.00 -90.00   48
 27  ω     50.00  77.00   1.00    1.00    --   38.88  38.00-180.00   27
 28  ω     10.00  52.00   1.00    1.00    --   38.88  19.00 120.00   42
 29  ω     33.00  62.00   1.00    1.00    --   38.88 -99.00 -30.00   29
 30  ω    -29.00  67.00   1.00    1.00    --   38.88 -19.00-150.00   96
 31  ω     45.00  72.00   1.00    1.00    --   38.88  19.00 -60.00   27
 32  ω     24.00  49.00   1.00    1.00    --   38.88  38.00 -90.00   25
 33  ω      1.00  28.00   1.00    1.00    --   38.88 -77.00-120.00   27
 34  ω     60.00  98.00   1.00    1.00    --   38.88  77.00-180.00   38
 35  ω    -21.00   6.00   1.00    1.00    --   38.88 -38.00-120.00   27
 36  ω     24.00  69.00   1.00    1.00    --   38.88  77.00  60.00   45
 37  ω     -6.00  25.00   1.00    1.00    --   38.88  12.00-121.40   31
 38  ω     33.00  62.00   1.00    1.00    --   38.88  57.00-120.00   29
 39  ω     24.00  51.00   1.00    1.00    --   38.88  57.00 -90.00   27
 40  ω     79.00 106.00   1.00    1.00    --   38.88  57.00 -90.00   27
 41  ω    -27.00   4.00   1.00    1.00    --   38.88 -57.00  90.00   31
 42  ω     71.00 101.00   1.00    1.00    --   38.88  19.00-150.00   30
 43  ω     54.00  81.00   1.00    1.00    --   38.88  38.00  60.00   27
 44  ω     82.00 108.00   1.00    1.00    --   38.88  38.00  60.00   26
 45  ω     43.00 106.00   1.00    1.00    --   38.88  57.00 -30.00   63
 46  ω     13.00  51.00   1.00    1.00    --   38.88  77.00-180.00   38
 47  ω      9.00  38.00   1.00    1.00    --   38.88 -77.00-150.00   29
 48  ω     40.00  92.00   1.00    1.00    --   38.88-125.00  60.00   52
 49  ω     59.00  84.00   1.00    1.00    --   38.88-125.00-120.00   25
 50  ω     99.00 150.00   1.00    3.00    --  111.00  45.00  90.00   51
 51  ω    103.00 174.00   1.00    3.00    --  111.00  45.00 -60.00   71
 52  ω     60.00 126.00   1.00    3.00    --  111.00 -30.00-150.00   66
 53  ω    134.00 161.00   1.00    3.00    --  111.00  77.00 -90.00   27
 54  ω    104.00 149.00   1.00    3.00    --  111.00 111.00   0.00   45
 55  ω     85.00 111.00   1.00    3.00    --  111.00  77.00 -90.00   26
 56  ω     94.00 121.00   1.00    3.00    --  111.00  30.00  90.00   27
 57  ω    102.00 131.00   1.00    3.00    --  111.00 -77.00 150.00   29
 58  ω     49.00  76.00   1.00    3.00    --  111.00 -77.00 150.00   27
 59  ω     49.00  79.00   1.00    3.00    --  111.00 -94.00 -60.00   30
 60  ω     71.00 116.00   1.00    3.00    --  111.00-111.00 -30.00   45
 61  ω     45.00 129.00   1.00    3.00    --  111.00 -77.00 -30.00   84
 62  ω     55.00  82.00   1.00    3.00    --  111.00 -61.00 -60.00   27
 63  ω     59.00 132.00   1.00    3.00    --  111.00 178.00 -60.00   73
 64  ω     85.00 130.00   1.00    3.00    --  111.00 -34.00 -23.78   45
 65  ω     93.00 127.00   1.00    3.00    --  111.00  61.00-150.00   34
 66  ω    106.00 141.00   1.00    3.00    --  111.00  45.00 120.00   35
 67  ω     95.00 155.00   1.00    3.00    --  111.00  45.00-180.00   60
 68  ω     56.00 112.00   1.00    3.00    --  111.00-111.00 120.00   56
 69  ω     99.00 138.00   1.00    3.00    --  111.00  61.00   0.00   39
 70  ω     65.00 118.00   1.00    3.00    --  111.00 -45.00 -90.00   53
 71  ω     84.00 176.00   1.00    3.00    --  111.00  77.00  30.00   92
 72  ω    105.00 132.00   1.00    3.00    --  111.00 -30.00 150.00   27
 73  ω     65.00  92.00   1.00    3.00    --  111.00 -45.00  30.00   27
 74  ω     51.00 111.00   1.00    3.00    --  111.00-111.00-120.00   60
 75  ω    119.00 176.00   1.00    3.00    --  111.00 111.00 -90.00   57
 76  ω     54.00 127.00   1.00    3.00    --  111.00 -55.00-143.85   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0774120000
_diffrn_orient_matrix_UB_12      0.0038814000
_diffrn_orient_matrix_UB_13      0.0528209000
_diffrn_orient_matrix_UB_21      -0.0667606000
_diffrn_orient_matrix_UB_22      -0.1052187000
_diffrn_orient_matrix_UB_23      -0.0089907000
_diffrn_orient_matrix_UB_31      0.1722764000
_diffrn_orient_matrix_UB_32      -0.0389785000
_diffrn_orient_matrix_UB_33      0.0295179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                9346
_reflns_number_total             9802
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 4028 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9802
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+5.9903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          'Refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C20(H20), C23(H23),
 C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C17A(H17A), C20A(H20A),
 C23A(H23A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6A(H6AA,H6AB)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C9A(H9A), C10A(H10A), C11A(H11A),
 C12A(H12A)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C13A(H13D,H13E,H13F),
 C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F), C18A(H18D,
 H18E,H18F), C19A(H19D,H19E,H19F), C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F),
 C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.74511(17) 0.77485(11) 0.80875(5) 0.0146(3) Uani 1 1 d . . . . .
O1 O 0.6074(5) 0.7742(3) 1.05853(13) 0.0169(7) Uani 1 1 d . . . . .
O2 O 0.2633(5) 0.8224(3) 0.95254(14) 0.0192(7) Uani 1 1 d . . . . .
O3 O 0.2143(5) 0.6226(3) 0.96789(15) 0.0187(8) Uani 1 1 d . . . . .
O4 O 0.5325(5) 0.5543(3) 0.93831(15) 0.0196(8) Uani 1 1 d . . . . .
O5 O 0.6381(5) 0.8097(3) 0.96980(13) 0.0146(7) Uani 1 1 d . . . . .
O6 O 0.6754(5) 0.7328(3) 0.86376(14) 0.0171(8) Uani 1 1 d . . . . .
C1 C 0.5350(6) 0.8229(4) 1.01091(18) 0.0159(10) Uani 1 1 d . . . . .
H1 H 0.522789 0.892601 1.017915 0.019 Uiso 1 1 calc R . . . .
C2 C 0.3562(6) 0.7768(4) 0.99773(19) 0.0153(10) Uani 1 1 d . . . . .
H2 H 0.291116 0.784137 1.028083 0.018 Uiso 1 1 calc R . . . .
C3 C 0.3745(6) 0.6682(4) 0.9854(2) 0.0139(10) Uani 1 1 d . . . . .
H3 H 0.427994 0.635194 1.017655 0.017 Uiso 1 1 calc R . . . .
C4 C 0.4923(6) 0.6556(4) 0.9424(2) 0.0139(10) Uani 1 1 d . . . . .
H4 H 0.433415 0.679391 0.908358 0.017 Uiso 1 1 calc R . . . .
C5 C 0.6644(7) 0.7098(4) 0.9568(2) 0.0146(10) Uani 1 1 d . . . . .
H5 H 0.728301 0.678065 0.988020 0.017 Uiso 1 1 calc R . . . .
C6 C 0.7773(7) 0.7072(4) 0.91235(19) 0.0164(11) Uani 1 1 d . . . . .
H6A H 0.873119 0.752687 0.919914 0.020 Uiso 1 1 calc R . . . .
H6B H 0.825266 0.642382 0.909591 0.020 Uiso 1 1 calc R . . . .
C7 C 0.7735(7) 0.7981(3) 1.0819(2) 0.0146(10) Uani 1 1 d . . . . .
C8 C 0.8545(7) 0.7260(4) 1.1152(2) 0.0199(11) Uani 1 1 d . . . . .
C9 C 1.0175(7) 0.7462(5) 1.1426(2) 0.0274(14) Uani 1 1 d . . . . .
H9 H 1.073478 0.699225 1.165106 0.033 Uiso 1 1 calc R . . . .
C10 C 1.0980(8) 0.8352(6) 1.1371(2) 0.0328(15) Uani 1 1 d . . . . .
H10 H 1.206417 0.847956 1.156095 0.039 Uiso 1 1 calc R . . . .
C11 C 1.0160(8) 0.9053(5) 1.1030(2) 0.0292(14) Uani 1 1 d . . . . .
H11 H 1.069970 0.964882 1.098837 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8531(8) 0.8861(4) 1.0750(2) 0.0231(12) Uani 1 1 d . . . . .
H12 H 0.798352 0.932390 1.051858 0.028 Uiso 1 1 calc R . . . .
C13 C 0.7640(9) 0.6304(5) 1.1216(2) 0.0300(14) Uani 1 1 d . . . . .
H13A H 0.657983 0.641915 1.136335 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.838341 0.588731 1.144886 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.737832 0.599568 1.087533 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.1679(8) 0.9052(4) 0.9654(2) 0.0250(13) Uani 1 1 d . . . . .
H14A H 0.115524 0.936047 0.933327 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.244690 0.950367 0.985558 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.078688 0.885352 0.986035 0.038 Uiso 1 1 calc GR . . . .
C15 C 0.1120(7) 0.6077(5) 1.0096(2) 0.0291(14) Uani 1 1 d . . . . .
H15A H 0.009115 0.571871 0.996406 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.079793 0.669623 1.022949 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.178006 0.571511 1.037655 0.044 Uiso 1 1 calc GR . . . .
C16 C 0.4901(8) 0.5155(4) 0.8865(2) 0.0231(12) Uani 1 1 d . . . . .
H16A H 0.549796 0.551679 0.862085 0.035 Uiso 1 1 calc GR . . . .
H16B H 0.366869 0.520273 0.876129 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.524747 0.448362 0.886343 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.8608(7) 0.8937(4) 0.8230(2) 0.0207(11) Uani 1 1 d . . . . .
H17 H 0.973855 0.877627 0.843021 0.025 Uiso 1 1 calc R . . . .
C18 C 0.7715(8) 0.9634(5) 0.8581(2) 0.0286(13) Uani 1 1 d . . . . .
H18A H 0.660835 0.982828 0.839753 0.043 Uiso 1 1 calc GR . . . .
H18B H 0.843057 1.019944 0.866035 0.043 Uiso 1 1 calc GR . . . .
H18C H 0.754699 0.931010 0.890566 0.043 Uiso 1 1 calc GR . . . .
C19 C 0.9004(9) 0.9470(5) 0.7720(3) 0.0322(15) Uani 1 1 d . . . . .
H19A H 0.956860 0.902804 0.750442 0.048 Uiso 1 1 calc GR . . . .
H19B H 0.975250 1.001595 0.781682 0.048 Uiso 1 1 calc GR . . . .
H19C H 0.793694 0.969481 0.752429 0.048 Uiso 1 1 calc GR . . . .
C20 C 0.5357(7) 0.7825(4) 0.7624(2) 0.0201(11) Uani 1 1 d . . . . .
H20 H 0.476861 0.720088 0.765843 0.024 Uiso 1 1 calc R . . . .
C21 C 0.4106(8) 0.8606(5) 0.7780(2) 0.0294(14) Uani 1 1 d . . . . .
H21A H 0.404529 0.856848 0.815474 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.297088 0.849970 0.758904 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.451817 0.923906 0.769477 0.044 Uiso 1 1 calc GR . . . .
C22 C 0.5583(8) 0.7915(5) 0.7036(2) 0.0259(13) Uani 1 1 d . . . . .
H22A H 0.611555 0.852951 0.697492 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.446643 0.787686 0.682386 0.039 Uiso 1 1 calc GR . . . .
H22C H 0.630912 0.739474 0.693966 0.039 Uiso 1 1 calc GR . . . .
C23 C 0.8961(7) 0.6842(4) 0.7823(2) 0.0196(11) Uani 1 1 d . . . . .
H23 H 0.920726 0.708803 0.747798 0.023 Uiso 1 1 calc R . . . .
C24 C 1.0722(7) 0.6731(5) 0.8175(2) 0.0290(14) Uani 1 1 d . . . . .
H24A H 1.127509 0.735654 0.822348 0.043 Uiso 1 1 calc GR . . . .
H24B H 1.145219 0.629532 0.800800 0.043 Uiso 1 1 calc GR . . . .
H24C H 1.053587 0.647219 0.851455 0.043 Uiso 1 1 calc GR . . . .
C25 C 0.8097(8) 0.5842(4) 0.7724(2) 0.0263(13) Uani 1 1 d . . . . .
H25A H 0.787728 0.556563 0.805560 0.039 Uiso 1 1 calc GR . . . .
H25B H 0.885301 0.541940 0.755828 0.039 Uiso 1 1 calc GR . . . .
H25C H 0.701766 0.591628 0.749499 0.039 Uiso 1 1 calc GR . . . .
Si1A Si 0.28425(17) 0.32389(11) 0.68250(5) 0.0125(3) Uani 1 1 d . . . . .
O1A O 0.3703(4) 0.2742(3) 0.43647(13) 0.0147(7) Uani 1 1 d . . . . .
O2A O 0.7400(4) 0.3190(3) 0.53501(13) 0.0169(7) Uani 1 1 d . . . . .
O3A O 0.7693(5) 0.1196(3) 0.52778(14) 0.0168(8) Uani 1 1 d . . . . .
O4A O 0.4551(5) 0.0617(3) 0.56306(14) 0.0175(8) Uani 1 1 d . . . . .
O5A O 0.3651(4) 0.3175(3) 0.52527(13) 0.0154(7) Uani 1 1 d . . . . .
O6A O 0.3293(5) 0.2492(2) 0.63516(13) 0.0154(7) Uani 1 1 d . . . . .
C1A C 0.4603(6) 0.3231(4) 0.48176(18) 0.0144(9) Uani 1 1 d . . . . .
H1A H 0.478971 0.391544 0.473011 0.017 Uiso 1 1 calc R . . . .
C2A C 0.6346(6) 0.2711(4) 0.49279(18) 0.0142(9) Uani 1 1 d . . . . .
H2A H 0.692962 0.272021 0.460818 0.017 Uiso 1 1 calc R . . . .
C3A C 0.6096(6) 0.1658(4) 0.50979(19) 0.0134(10) Uani 1 1 d . . . . .
H3A H 0.550303 0.129238 0.479592 0.016 Uiso 1 1 calc R . . . .
C4A C 0.4998(7) 0.1624(4) 0.5553(2) 0.0137(10) Uani 1 1 d . . . . .
H4A H 0.565738 0.188600 0.587777 0.016 Uiso 1 1 calc R . . . .
C5A C 0.3308(6) 0.2202(4) 0.54109(19) 0.0135(10) Uani 1 1 d . . . . .
H5A H 0.261357 0.187492 0.511228 0.016 Uiso 1 1 calc R . . . .
C6A C 0.2217(7) 0.2272(4) 0.58663(19) 0.0170(11) Uani 1 1 d . . . . .
H6AA H 0.134622 0.277760 0.579007 0.020 Uiso 1 1 calc R . . . .
H6AB H 0.162077 0.165871 0.590204 0.020 Uiso 1 1 calc R . . . .
C7A C 0.2136(6) 0.3135(4) 0.41336(18) 0.0132(10) Uani 1 1 d . . . . .
C8A C 0.1011(6) 0.2468(4) 0.3841(2) 0.0143(10) Uani 1 1 d . . . . .
C9A C -0.0520(7) 0.2838(5) 0.3567(2) 0.0217(12) Uani 1 1 d . . . . .
H9A H -0.128256 0.241637 0.336749 0.026 Uiso 1 1 calc R . . . .
C10A C -0.0939(7) 0.3815(4) 0.3585(2) 0.0223(12) Uani 1 1 d . . . . .
H10A H -0.195902 0.404678 0.339227 0.027 Uiso 1 1 calc R . . . .
C11A C 0.0172(7) 0.4451(4) 0.3891(2) 0.0194(11) Uani 1 1 d . . . . .
H11A H -0.011549 0.510703 0.390999 0.023 Uiso 1 1 calc R . . . .
C12A C 0.1707(7) 0.4105(4) 0.4169(2) 0.0171(11) Uani 1 1 d . . . . .
H12A H 0.244490 0.452706 0.437768 0.020 Uiso 1 1 calc R . . . .
C13A C 0.1480(7) 0.1407(4) 0.3818(2) 0.0210(11) Uani 1 1 d . . . . .
H13D H 0.242087 0.132929 0.361096 0.031 Uiso 1 1 calc GR . . . .
H13E H 0.048938 0.104476 0.365800 0.031 Uiso 1 1 calc GR . . . .
H13F H 0.182815 0.116944 0.417153 0.031 Uiso 1 1 calc GR . . . .
C14A C 0.8324(8) 0.4000(4) 0.5183(2) 0.0251(13) Uani 1 1 d . . . . .
H14D H 0.910703 0.378407 0.494426 0.038 Uiso 1 1 calc GR . . . .
H14E H 0.897263 0.430415 0.548690 0.038 Uiso 1 1 calc GR . . . .
H14F H 0.751676 0.446078 0.500562 0.038 Uiso 1 1 calc GR . . . .
C15A C 0.8703(7) 0.0990(5) 0.4866(2) 0.0278(13) Uani 1 1 d . . . . .
H15D H 0.804278 0.059000 0.460288 0.042 Uiso 1 1 calc GR . . . .
H15E H 0.974054 0.065011 0.501018 0.042 Uiso 1 1 calc GR . . . .
H15F H 0.901153 0.158814 0.470651 0.042 Uiso 1 1 calc GR . . . .
C16A C 0.4792(8) 0.0325(4) 0.6169(2) 0.0216(12) Uani 1 1 d . . . . .
H16D H 0.458252 -0.036291 0.619189 0.032 Uiso 1 1 calc GR . . . .
H16E H 0.399506 0.067250 0.635972 0.032 Uiso 1 1 calc GR . . . .
H16F H 0.596329 0.046594 0.632236 0.032 Uiso 1 1 calc GR . . . .
C17A C 0.2947(7) 0.4532(4) 0.6583(2) 0.0188(11) Uani 1 1 d . . . . .
H17A H 0.197752 0.462417 0.629954 0.023 Uiso 1 1 calc R . . . .
C18A C 0.4634(7) 0.4744(4) 0.6348(2) 0.0246(12) Uani 1 1 d . . . . .
H18D H 0.561062 0.466470 0.661761 0.037 Uiso 1 1 calc GR . . . .
H18E H 0.460832 0.540011 0.621590 0.037 Uiso 1 1 calc GR . . . .
H18F H 0.473640 0.429842 0.606175 0.037 Uiso 1 1 calc GR . . . .
C19A C 0.2720(8) 0.5273(4) 0.7023(3) 0.0293(14) Uani 1 1 d . . . . .
H19D H 0.162982 0.516012 0.715333 0.044 Uiso 1 1 calc GR . . . .
H19E H 0.273745 0.592144 0.688208 0.044 Uiso 1 1 calc GR . . . .
H19F H 0.365197 0.519933 0.730833 0.044 Uiso 1 1 calc GR . . . .
C20A C 0.4610(6) 0.3005(4) 0.7395(2) 0.0170(11) Uani 1 1 d . . . . .
H20A H 0.557438 0.344515 0.734869 0.020 Uiso 1 1 calc R . . . .
C21A C 0.5344(8) 0.1953(5) 0.7411(2) 0.0265(13) Uani 1 1 d . . . . .
H21D H 0.442993 0.149874 0.745216 0.040 Uiso 1 1 calc GR . . . .
H21E H 0.625062 0.189026 0.770407 0.040 Uiso 1 1 calc GR . . . .
H21F H 0.580597 0.181839 0.708545 0.040 Uiso 1 1 calc GR . . . .
C22A C 0.4007(8) 0.3253(5) 0.7932(2) 0.0265(12) Uani 1 1 d . . . . .
H22D H 0.366198 0.392522 0.793320 0.040 Uiso 1 1 calc GR . . . .
H22E H 0.494468 0.314317 0.821135 0.040 Uiso 1 1 calc GR . . . .
H22F H 0.303886 0.284681 0.798640 0.040 Uiso 1 1 calc GR . . . .
C23A C 0.0636(6) 0.2971(4) 0.7029(2) 0.0157(11) Uani 1 1 d . . . . .
H23A H 0.058521 0.330541 0.736749 0.019 Uiso 1 1 calc R . . . .
C24A C -0.0907(7) 0.3344(5) 0.6640(2) 0.0254(12) Uani 1 1 d . . . . .
H24D H -0.078047 0.403098 0.658600 0.038 Uiso 1 1 calc GR . . . .
H24E H -0.197123 0.322283 0.678453 0.038 Uiso 1 1 calc GR . . . .
H24F H -0.093378 0.300960 0.630711 0.038 Uiso 1 1 calc GR . . . .
C25A C 0.0411(8) 0.1875(4) 0.7132(2) 0.0245(12) Uani 1 1 d . . . . .
H25D H 0.045821 0.151908 0.680841 0.037 Uiso 1 1 calc GR . . . .
H25E H -0.069226 0.176504 0.725458 0.037 Uiso 1 1 calc GR . . . .
H25F H 0.132664 0.165613 0.739622 0.037 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O6 1.666(4) . ?
Si1 C17 1.873(6) . ?
Si1 C20 1.881(5) . ?
Si1 C23 1.891(6) . ?
O1 C1 1.431(6) . ?
O1 C7 1.385(6) . ?
O2 C2 1.419(6) . ?
O2 C14 1.418(7) . ?
O3 C3 1.411(6) . ?
O3 C15 1.418(6) . ?
O4 C4 1.431(6) . ?
O4 C16 1.417(7) . ?
O5 C1 1.407(6) . ?
O5 C5 1.430(6) . ?
O6 C6 1.421(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.522(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.532(7) . ?
C3 H3 0.9800 . ?
C3 C4 1.522(7) . ?
C4 H4 0.9800 . ?
C4 C5 1.531(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.517(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.397(7) . ?
C7 C12 1.378(8) . ?
C8 C9 1.390(8) . ?
C8 C13 1.507(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(8) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9800 . ?
C17 C18 1.534(8) . ?
C17 C19 1.552(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9800 . ?
C20 C21 1.532(8) . ?
C20 C22 1.533(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9800 . ?
C23 C24 1.541(8) . ?
C23 C25 1.533(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
Si1A O6A 1.651(4) . ?
Si1A C17A 1.883(5) . ?
Si1A C20A 1.887(5) . ?
Si1A C23A 1.888(5) . ?
O1A C1A 1.433(6) . ?
O1A C7A 1.388(6) . ?
O2A C2A 1.423(6) . ?
O2A C14A 1.416(7) . ?
O3A C3A 1.413(6) . ?
O3A C15A 1.414(6) . ?
O4A C4A 1.444(6) . ?
O4A C16A 1.415(7) . ?
O5A C1A 1.409(6) . ?
O5A C5A 1.430(6) . ?
O6A C6A 1.428(6) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.522(7) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.527(7) . ?
C3A H3A 0.9800 . ?
C3A C4A 1.524(6) . ?
C4A H4A 0.9800 . ?
C4A C5A 1.535(7) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.523(7) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A C8A 1.408(7) . ?
C7A C12A 1.378(8) . ?
C8A C9A 1.392(7) . ?
C8A C13A 1.502(7) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.381(8) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.391(8) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.386(8) . ?
C12A H12A 0.9300 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17A 0.9800 . ?
C17A C18A 1.535(8) . ?
C17A C19A 1.537(8) . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?
C19A H19D 0.9600 . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C20A H20A 0.9800 . ?
C20A C21A 1.550(8) . ?
C20A C22A 1.537(7) . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A H23A 0.9800 . ?
C23A C24A 1.538(7) . ?
C23A C25A 1.540(7) . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 0.9600 . ?
C25A H25D 0.9600 . ?
C25A H25E 0.9600 . ?
C25A H25F 0.9600 . ?

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
O6 Si1 C17 109.8(2) . . ?
O6 Si1 C20 101.3(2) . . ?
O6 Si1 C23 110.8(2) . . ?
C17 Si1 C20 115.2(3) . . ?
C17 Si1 C23 109.7(3) . . ?
C20 Si1 C23 109.8(3) . . ?
C7 O1 C1 119.5(4) . . ?
C14 O2 C2 113.1(4) . . ?
C3 O3 C15 112.5(4) . . ?
C16 O4 C4 113.9(4) . . ?
C1 O5 C5 114.0(4) . . ?
C6 O6 Si1 127.6(3) . . ?
O1 C1 H1 109.8 . . ?
O1 C1 C2 103.8(4) . . ?
O5 C1 O1 111.7(4) . . ?
O5 C1 H1 109.8 . . ?
O5 C1 C2 111.9(4) . . ?
C2 C1 H1 109.8 . . ?
O2 C2 C1 110.3(4) . . ?
O2 C2 H2 109.4 . . ?
O2 C2 C3 108.3(4) . . ?
C1 C2 H2 109.4 . . ?
C1 C2 C3 110.1(4) . . ?
C3 C2 H2 109.4 . . ?
O3 C3 C2 113.3(4) . . ?
O3 C3 H3 108.6 . . ?
O3 C3 C4 108.0(4) . . ?
C2 C3 H3 108.6 . . ?
C4 C3 C2 109.7(4) . . ?
C4 C3 H3 108.6 . . ?
O4 C4 C3 108.6(4) . . ?
O4 C4 H4 109.9 . . ?
O4 C4 C5 107.3(4) . . ?
C3 C4 H4 109.9 . . ?
C3 C4 C5 111.0(4) . . ?
C5 C4 H4 109.9 . . ?
O5 C5 C4 112.0(4) . . ?
O5 C5 H5 108.2 . . ?
O5 C5 C6 107.9(4) . . ?
C4 C5 H5 108.2 . . ?
C6 C5 C4 112.3(4) . . ?
C6 C5 H5 108.2 . . ?
O6 C6 C5 109.3(4) . . ?
O6 C6 H6A 109.8 . . ?
O6 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
O1 C7 C8 114.3(5) . . ?
C12 C7 O1 124.1(5) . . ?
C12 C7 C8 121.5(5) . . ?
C7 C8 C13 120.1(5) . . ?
C9 C8 C7 118.1(5) . . ?
C9 C8 C13 121.7(5) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(6) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(6) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(6) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 119.6(6) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17 106.2 . . ?
C18 C17 Si1 114.4(4) . . ?
C18 C17 H17 106.2 . . ?
C18 C17 C19 110.2(5) . . ?
C19 C17 Si1 113.0(4) . . ?
C19 C17 H17 106.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20 105.7 . . ?
C21 C20 Si1 113.7(4) . . ?
C21 C20 H20 105.7 . . ?
C21 C20 C22 110.7(5) . . ?
C22 C20 Si1 114.6(4) . . ?
C22 C20 H20 105.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C23 H23 107.0 . . ?
C24 C23 Si1 113.7(4) . . ?
C24 C23 H23 107.0 . . ?
C25 C23 Si1 111.6(4) . . ?
C25 C23 H23 107.0 . . ?
C25 C23 C24 110.1(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6A Si1A C17A 109.0(2) . . ?
O6A Si1A C20A 104.6(2) . . ?
O6A Si1A C23A 111.4(2) . . ?
C17A Si1A C20A 110.6(2) . . ?
C17A Si1A C23A 110.6(2) . . ?
C20A Si1A C23A 110.5(2) . . ?
C7A O1A C1A 117.8(4) . . ?
C14A O2A C2A 113.6(4) . . ?
C3A O3A C15A 113.4(4) . . ?
C16A O4A C4A 113.5(4) . . ?
C1A O5A C5A 114.0(4) . . ?
C6A O6A Si1A 127.2(3) . . ?
O1A C1A H1A 109.7 . . ?
O1A C1A C2A 104.9(4) . . ?
O5A C1A O1A 110.7(4) . . ?
O5A C1A H1A 109.7 . . ?
O5A C1A C2A 112.0(4) . . ?
C2A C1A H1A 109.7 . . ?
O2A C2A C1A 109.4(4) . . ?
O2A C2A H2A 109.6 . . ?
O2A C2A C3A 107.8(4) . . ?
C1A C2A H2A 109.6 . . ?
C1A C2A C3A 110.7(4) . . ?
C3A C2A H2A 109.6 . . ?
O3A C3A C2A 112.2(4) . . ?
O3A C3A H3A 109.1 . . ?
O3A C3A C4A 107.1(4) . . ?
C2A C3A H3A 109.1 . . ?
C4A C3A C2A 110.4(4) . . ?
C4A C3A H3A 109.1 . . ?
O4A C4A C3A 107.5(4) . . ?
O4A C4A H4A 110.2 . . ?
O4A C4A C5A 108.3(4) . . ?
C3A C4A H4A 110.2 . . ?
C3A C4A C5A 110.5(4) . . ?
C5A C4A H4A 110.2 . . ?
O5A C5A C4A 111.4(4) . . ?
O5A C5A H5A 108.3 . . ?
O5A C5A C6A 107.2(4) . . ?
C4A C5A H5A 108.3 . . ?
C6A C5A C4A 113.3(4) . . ?
C6A C5A H5A 108.3 . . ?
O6A C6A C5A 110.4(4) . . ?
O6A C6A H6AA 109.6 . . ?
O6A C6A H6AB 109.6 . . ?
C5A C6A H6AA 109.6 . . ?
C5A C6A H6AB 109.6 . . ?
H6AA C6A H6AB 108.1 . . ?
O1A C7A C8A 114.8(5) . . ?
C12A C7A O1A 123.6(5) . . ?
C12A C7A C8A 121.6(5) . . ?
C7A C8A C13A 120.9(5) . . ?
C9A C8A C7A 117.1(5) . . ?
C9A C8A C13A 122.0(5) . . ?
C8A C9A H9A 119.1 . . ?
C10A C9A C8A 121.9(5) . . ?
C10A C9A H9A 119.1 . . ?
C9A C10A H10A 120.2 . . ?
C9A C10A C11A 119.7(5) . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A C10A 119.9(5) . . ?
C12A C11A H11A 120.0 . . ?
C7A C12A C11A 119.7(5) . . ?
C7A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C8A C13A H13D 109.5 . . ?
C8A C13A H13E 109.5 . . ?
C8A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
O2A C14A H14D 109.5 . . ?
O2A C14A H14E 109.5 . . ?
O2A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
O3A C15A H15D 109.5 . . ?
O3A C15A H15E 109.5 . . ?
O3A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
O4A C16A H16D 109.5 . . ?
O4A C16A H16E 109.5 . . ?
O4A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
Si1A C17A H17A 107.5 . . ?
C18A C17A Si1A 112.4(4) . . ?
C18A C17A H17A 107.5 . . ?
C18A C17A C19A 110.0(5) . . ?
C19A C17A Si1A 111.8(4) . . ?
C19A C17A H17A 107.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
Si1A C20A H20A 107.1 . . ?
C21A C20A Si1A 114.0(4) . . ?
C21A C20A H20A 107.1 . . ?
C22A C20A Si1A 111.6(4) . . ?
C22A C20A H20A 107.1 . . ?
C22A C20A C21A 109.6(5) . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20A C22A H22D 109.5 . . ?
C20A C22A H22E 109.5 . . ?
C20A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
Si1A C23A H23A 106.9 . . ?
C24A C23A Si1A 114.6(4) . . ?
C24A C23A H23A 106.9 . . ?
C24A C23A C25A 109.7(5) . . ?
C25A C23A Si1A 111.3(4) . . ?
C25A C23A H23A 106.9 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C23A C25A H25D 109.5 . . ?
C23A C25A H25E 109.5 . . ?
C23A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?

_olex2_date_sample_data_collection 2019-11-15
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.827
####################################################################### 
# 
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 2059249'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        (2?-t-butylphenyl)-α-L-rhamnopyranoside
_chemical_formula_moiety         'C19 H28 O6'
_chemical_formula_sum            'C19 H28 O6'
_chemical_formula_weight         352.41
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H28O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   10.18301(10)
_cell_length_b                   13.55501(11)
_cell_length_c                   13.69931(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1890.93(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8612
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6280
_cell_measurement_theta_min      4.5570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 1 -3 0.0711
-4 1 7 0.0373
6 -3 3 0.0771
0 8 3 0.0311
1 -9 -1 0.0601
0 -7 5 0.0608
4 0 -7 0.0755
-1 2 -9 0.0665
2 -7 -5 0.0659
-6 -2 4 0.0742

_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.112
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.0399 0.9904 -3.4750 0.2904 -0.3375 0.8954
-3.5449 0.5967 7.4804 0.9518 -0.2281 -0.2053
5.6872 -3.2447 3.1317 -0.3778 0.0891 -0.9216
-0.0784 8.1611 3.3183 0.6069 0.7919 0.0677
1.2682 -8.5172 -1.4288 -0.5717 -0.7454 -0.3429
0.2059 -7.0796 5.2736 0.1299 -0.7037 -0.6985
3.9956 -0.0059 -6.9953 -0.9282 0.3184 0.1467
-0.9980 1.9932 -8.9926 -0.5689 0.1534 0.8653
1.9942 -6.9975 -4.9942 -0.8675 -0.5292 -0.0812
-5.9945 -1.9932 3.9991 0.7795 -0.6545 0.2016

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12760
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.822
_diffrn_reflns_theta_min         4.589
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  31.00   1.00    1.00    --  -36.45  77.00-120.00   94
  2  ω   -109.00 -39.00   1.00    1.00    --  -36.45-178.00 -30.00   70
  3  ω   -109.00 -39.00   1.00    1.00    --  -36.45-178.00 -90.00   70
  4  ω     61.00 109.00   1.00    1.00    --   36.45 178.00  90.00   48
  5  ω     38.00 108.00   1.00    2.00    --  107.73-111.00  90.00   70
  6  ω     38.00 107.00   1.00    2.00    --  107.73 -94.00 150.00   69
  7  ω     41.00 126.00   1.00    2.00    --  107.73 -61.00   0.00   85
  8  ω     38.00 107.00   1.00    2.00    --  107.73 -94.00   0.00   69
  9  ω     40.00 134.00   1.00    2.00    --  107.73 -77.00-180.00   94
 10  ω     39.00 125.00   1.00    2.00    --  107.73 -45.00 -60.00   86
 11  ω   -104.00 -20.00   1.00    1.00    --  -36.45 -57.00  30.00   84
 12  ω   -104.00 -20.00   1.00    1.00    --  -36.45 -57.00 150.00   84
 13  ω   -103.00 -17.00   1.00    1.00    --  -36.45 -63.00 -71.00   86
 14  ω     69.00 178.00   1.00    2.00    --  107.73  15.00 -90.00  109
 15  ω     90.00 176.00   1.00    2.00    --  107.73  45.00 120.00   86
 16  ω     38.00 177.00   1.00    2.00    --  107.73   0.00  60.00  139
 17  ω     28.00  54.00   1.00    1.00    --   36.70-125.00-180.00   26
 18  ω    104.00 129.00   1.00    2.00    --  107.73 -30.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0886735000
_diffrn_orient_matrix_UB_12      0.0401653000
_diffrn_orient_matrix_UB_13      0.0820095000
_diffrn_orient_matrix_UB_21      0.0740290000
_diffrn_orient_matrix_UB_22      0.0990913000
_diffrn_orient_matrix_UB_23      -0.0033108000
_diffrn_orient_matrix_UB_31      -0.0977221000
_diffrn_orient_matrix_UB_32      0.0385928000
_diffrn_orient_matrix_UB_33      -0.0768260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3536
_reflns_number_total             3659
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1466 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.2935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          'Refined without restraint'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67346(11) 0.56391(8) 0.69410(8) 0.0136(2) Uani 1 1 d . . . . .
O2 O 0.32861(11) 0.50565(8) 0.71526(9) 0.0149(2) Uani 1 1 d . . . . .
O3 O 0.33697(11) 0.66340(8) 0.83891(9) 0.0138(2) Uani 1 1 d . . . . .
O4 O 0.38798(12) 0.81079(8) 0.69135(9) 0.0159(3) Uani 1 1 d . . . . .
O5 O 0.50900(11) 0.58418(8) 0.57501(8) 0.0150(2) Uani 1 1 d . . . . .
O6 O 0.46151(13) 0.77288(9) 0.92291(9) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.54938(16) 0.53164(12) 0.65795(12) 0.0127(3) Uani 1 1 d . . . . .
H1 H 0.555442 0.461480 0.641292 0.015 Uiso 1 1 calc R . . . .
C2 C 0.45279(15) 0.54393(11) 0.74264(12) 0.0119(3) Uani 1 1 d . . . . .
H2 H 0.485566 0.509619 0.800706 0.014 Uiso 1 1 calc R . . . .
C3 C 0.43585(16) 0.65364(12) 0.76407(12) 0.0121(3) Uani 1 1 d . . . . .
H3 H 0.519089 0.681418 0.787166 0.015 Uiso 1 1 calc R . . . .
C4 C 0.39162(16) 0.70738(11) 0.67239(12) 0.0127(3) Uani 1 1 d . . . . .
H4 H 0.304323 0.684224 0.652847 0.015 Uiso 1 1 calc R . . . .
C5 C 0.49036(17) 0.68867(12) 0.59001(13) 0.0153(3) Uani 1 1 d . . . . .
H5 H 0.574687 0.718909 0.607144 0.018 Uiso 1 1 calc R . . . .
C6 C 0.4440(2) 0.72971(14) 0.49321(14) 0.0249(4) Uani 1 1 d . . . . .
H6A H 0.508803 0.716597 0.443978 0.037 Uiso 1 1 calc GR . . . .
H6B H 0.431284 0.799645 0.498957 0.037 Uiso 1 1 calc GR . . . .
H6C H 0.362615 0.698931 0.475308 0.037 Uiso 1 1 calc GR . . . .
C7 C 0.78561(17) 0.53728(12) 0.64281(12) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.90569(16) 0.55539(12) 0.68960(12) 0.0139(3) Uani 1 1 d . . . . .
C9 C 1.01980(17) 0.53105(12) 0.63955(13) 0.0179(4) Uani 1 1 d . . . . .
H9 H 1.100597 0.543637 0.668645 0.021 Uiso 1 1 calc R . . . .
C10 C 1.01684(17) 0.48833(13) 0.54708(14) 0.0198(4) Uani 1 1 d . . . . .
H10 H 1.094626 0.472800 0.514985 0.024 Uiso 1 1 calc R . . . .
C11 C 0.89705(19) 0.46928(13) 0.50355(13) 0.0196(4) Uani 1 1 d . . . . .
H11 H 0.894260 0.439550 0.442407 0.023 Uiso 1 1 calc R . . . .
C12 C 0.78074(17) 0.49424(12) 0.55052(13) 0.0164(3) Uani 1 1 d . . . . .
H12 H 0.700315 0.482319 0.520596 0.020 Uiso 1 1 calc R . . . .
C13 C 0.91255(17) 0.60248(13) 0.79014(13) 0.0166(3) Uani 1 1 d . . . . .
H13 H 0.823846 0.603161 0.817877 0.020 Uiso 1 1 calc R . . . .
C14 C 0.9601(2) 0.70905(13) 0.78162(15) 0.0255(4) Uani 1 1 d . . . . .
H14A H 0.958063 0.739707 0.844773 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.903853 0.744625 0.737778 0.038 Uiso 1 1 calc GR . . . .
H14C H 1.048366 0.709781 0.756950 0.038 Uiso 1 1 calc GR . . . .
C15 C 1.00200(18) 0.54516(14) 0.85953(13) 0.0232(4) Uani 1 1 d . . . . .
H15A H 0.972900 0.477917 0.863439 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.998758 0.574605 0.923215 0.035 Uiso 1 1 calc GR . . . .
H15C H 1.090531 0.546976 0.835498 0.035 Uiso 1 1 calc GR . . . .
C16 C 0.31305(18) 0.40389(13) 0.73780(16) 0.0221(4) Uani 1 1 d . . . . .
H16A H 0.379697 0.366365 0.704964 0.033 Uiso 1 1 calc GR . . . .
H16B H 0.227987 0.382099 0.716624 0.033 Uiso 1 1 calc GR . . . .
H16C H 0.320952 0.394516 0.807006 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.36110(16) 0.72639(12) 0.91378(12) 0.0141(3) Uani 1 1 d . . . . .
C18 C 0.24685(18) 0.72853(14) 0.98227(14) 0.0205(4) Uani 1 1 d . . . . .
H18A H 0.174113 0.761077 0.951448 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.270784 0.763631 1.040472 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.222291 0.662239 0.998866 0.031 Uiso 1 1 calc GR . . . .
C19 C 0.26452(17) 0.85544(12) 0.67367(15) 0.0215(4) Uani 1 1 d . . . . .
H19A H 0.236213 0.840170 0.608561 0.032 Uiso 1 1 calc GR . . . .
H19B H 0.272267 0.925654 0.680829 0.032 Uiso 1 1 calc GR . . . .
H19C H 0.201403 0.830772 0.719643 0.032 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4259(19) . ?
O1 C7 1.3885(19) . ?
O2 C2 1.4174(19) . ?
O2 C16 1.4223(19) . ?
O3 C3 1.4430(19) . ?
O3 C17 1.357(2) . ?
O4 C4 1.4261(18) . ?
O4 C19 1.416(2) . ?
O5 C1 1.4025(19) . ?
O5 C5 1.4437(19) . ?
O6 C17 1.208(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.530(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.526(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.520(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.533(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.513(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.402(2) . ?
C7 C12 1.393(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.520(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C14 1.528(2) . ?
C13 C15 1.529(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.495(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C7 O1 C1 118.25(12) . . ?
C2 O2 C16 113.39(13) . . ?
C17 O3 C3 117.93(12) . . ?
C19 O4 C4 114.33(13) . . ?
C1 O5 C5 114.92(12) . . ?
O1 C1 H1 108.8 . . ?
O1 C1 C2 105.84(12) . . ?
O5 C1 O1 112.67(13) . . ?
O5 C1 H1 108.8 . . ?
O5 C1 C2 111.75(13) . . ?
C2 C1 H1 108.8 . . ?
O2 C2 C1 109.45(13) . . ?
O2 C2 H2 110.2 . . ?
O2 C2 C3 107.87(12) . . ?
C1 C2 H2 110.2 . . ?
C3 C2 C1 108.95(13) . . ?
C3 C2 H2 110.2 . . ?
O3 C3 C2 107.76(12) . . ?
O3 C3 H3 109.8 . . ?
O3 C3 C4 109.65(13) . . ?
C2 C3 H3 109.8 . . ?
C4 C3 C2 109.98(13) . . ?
C4 C3 H3 109.8 . . ?
O4 C4 C3 109.16(13) . . ?
O4 C4 H4 109.9 . . ?
O4 C4 C5 108.29(13) . . ?
C3 C4 H4 109.9 . . ?
C3 C4 C5 109.56(13) . . ?
C5 C4 H4 109.9 . . ?
O5 C5 C4 110.69(13) . . ?
O5 C5 H5 109.2 . . ?
O5 C5 C6 106.08(14) . . ?
C4 C5 H5 109.2 . . ?
C6 C5 C4 112.32(14) . . ?
C6 C5 H5 109.2 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 116.13(14) . . ?
O1 C7 C12 122.60(15) . . ?
C12 C7 C8 121.27(15) . . ?
C7 C8 C13 121.86(15) . . ?
C9 C8 C7 117.54(15) . . ?
C9 C8 C13 120.57(15) . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.97(16) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.27(16) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.47(16) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.46(16) . . ?
C11 C12 H12 120.3 . . ?
C8 C13 H13 108.2 . . ?
C8 C13 C14 110.02(14) . . ?
C8 C13 C15 112.18(15) . . ?
C14 C13 H13 108.2 . . ?
C14 C13 C15 109.82(15) . . ?
C15 C13 H13 108.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 110.22(14) . . ?
O6 C17 O3 124.05(15) . . ?
O6 C17 C18 125.73(15) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_date_sample_data_collection 2020-02-25
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.719
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2059247'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
(2?-t-butylphenyl)-2,3,4-tri-O-methyl-α-L-rhamnopyranoside
_chemical_formula_moiety         'C19 H30 O5'
_chemical_formula_sum            'C19 H30 O5'
_chemical_formula_weight         338.43
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H30O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.71828(6)
_cell_length_b                   13.89043(10)
_cell_length_c                   17.59797(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1886.68(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11413
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2480
_cell_measurement_theta_min      4.0280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 11 0.0417
0 1 -11 0.0417
-5 3 -1 0.0564
2 8 0 0.0445
-2 -8 -1 0.0442
0 -8 6 0.0311
2 -8 3 0.0589
5 -2 -3 0.0804

_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.083
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0026 -1.0021 10.9941 0.0223 0.2747 -0.9286
-0.0026 1.0021 -10.9941 -0.0223 -0.2747 0.9286
-4.9956 3.0064 -0.9900 0.5104 0.8368 0.3897
2.0056 7.9947 -0.0047 -0.8945 0.3361 0.1841
-2.0059 -7.9945 -0.9947 0.8994 -0.3678 -0.1027
-0.0047 -7.9988 5.9975 0.5731 -0.4040 -0.7556
1.9935 -8.0010 2.9953 0.2950 -0.7574 -0.5947
4.9952 -2.0058 -3.0079 -0.5664 -0.8894 -0.0307

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.444
_diffrn_reflns_theta_min         4.055
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00-120.00   84
  2  ω   -108.00  -8.00   1.00    1.00    --  -37.09 -19.00 150.00  100
  3  ω    -66.00  34.00   1.00    1.00    --  -37.09  19.00  60.00  100
  4  ω    -90.00  -2.00   1.00    1.00    --  -37.09 125.00  60.00   88
  5  ω     23.00  90.00   1.00    1.00    --   37.09-125.00 -60.00   67
  6  ω      1.00  76.00   1.00    1.00    --   37.09 -99.00  30.00   75
  7  ω     10.00 105.00   1.00    1.00    --   37.09  77.00 -60.00   95
  8  ω     42.00 109.00   1.00    2.48    --  111.00 -94.00 -60.00   67
  9  ω     43.00 128.00   1.00    2.48    --  111.00 -45.00  60.00   85
 10  ω     43.00 128.00   1.00    2.48    --  111.00 -45.00-120.00   85
 11  ω     84.00 178.00   1.00    2.48    --  111.00  77.00  60.00   94
 12  ω     57.00 150.00   1.00    2.48    --  111.00 178.00 150.00   93
 13  ω    100.00 178.00   1.00    2.48    --  111.00 111.00-120.00   78
 14  ω     44.00 129.00   1.00    2.48    --  111.00 -61.00 -90.00   85
 15  ω   -105.00 -10.00   1.00    1.00    --  -37.09 -77.00-150.00   95
 16  ω   -105.00 -10.00   1.00    1.00    --  -37.09 -77.00  30.00   95
 17  ω   -105.00 -10.00   1.00    1.00    --  -37.09 -77.00 120.00   95
 18  ω    -54.00  30.00   1.00    1.00    --  -37.09  57.00 -60.00   84
 19  ω     18.00 106.00   1.00    1.00    --   37.09  38.00  90.00   88
 20  ω    -32.00  56.00   1.00    1.00    --   37.09 -38.00 150.00   88
 21  ω     84.00 178.00   1.00    2.48    --  111.00  77.00   0.00   94
 22  ω     42.00 109.00   1.00    2.48    --  111.00 -94.00-180.00   67
 23  ω     73.00 178.00   1.00    2.48    --  111.00  15.00 -60.00  105
 24  ω     73.00 118.00   1.00    2.48    --  111.00  15.00  30.00   45
 25  ω     73.00 178.00   1.00    2.48    --  111.00  15.00-180.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1464574000
_diffrn_orient_matrix_UB_12      -0.0751539000
_diffrn_orient_matrix_UB_13      -0.0047871000
_diffrn_orient_matrix_UB_21      -0.1290164000
_diffrn_orient_matrix_UB_22      0.0744257000
_diffrn_orient_matrix_UB_23      0.0318047000
_diffrn_orient_matrix_UB_31      -0.0417386000
_diffrn_orient_matrix_UB_32      0.0334490000
_diffrn_orient_matrix_UB_33      -0.0814018000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3647
_reflns_number_total             3759
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.2886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0708
_refine_special_details          'refined without restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67013(14) 0.45357(8) 0.67713(6) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.39327(15) 0.52066(9) 0.83105(7) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.26405(15) 0.33045(9) 0.79530(7) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.56655(16) 0.23127(8) 0.84639(7) 0.0241(3) Uani 1 1 d . . . . .
O5 O 0.74216(15) 0.47081(8) 0.80621(6) 0.0197(2) Uani 1 1 d . . . . .
C1 C 0.6299(2) 0.49903(12) 0.74754(9) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.636236 0.569038 0.741202 0.023 Uiso 1 1 calc R . . . .
C2 C 0.4434(2) 0.47020(12) 0.76395(9) 0.0193(3) Uani 1 1 d . . . . .
H2 H 0.368545 0.488662 0.721404 0.023 Uiso 1 1 calc R . . . .
C3 C 0.4343(2) 0.36151(12) 0.77672(9) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.471422 0.328796 0.730141 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5559(2) 0.33367(11) 0.84067(9) 0.0185(3) Uani 1 1 d . . . . .
H4 H 0.514720 0.360881 0.888767 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7398(2) 0.36926(11) 0.82401(9) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.786195 0.333347 0.780599 0.022 Uiso 1 1 calc R . . . .
C6 C 0.8602(2) 0.35644(13) 0.89095(10) 0.0239(4) Uani 1 1 d . . . . .
H6A H 0.974620 0.377216 0.877180 0.036 Uiso 1 1 calc GR . . . .
H6B H 0.863319 0.289761 0.905245 0.036 Uiso 1 1 calc GR . . . .
H6C H 0.819225 0.394184 0.932959 0.036 Uiso 1 1 calc GR . . . .
C7 C 0.8078(2) 0.48645(11) 0.63403(9) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.8166(2) 0.45108(11) 0.55884(9) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.9545(2) 0.48464(12) 0.51464(10) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.963778 0.463804 0.464586 0.026 Uiso 1 1 calc R . . . .
C10 C 1.0779(2) 0.54783(13) 0.54272(11) 0.0253(4) Uani 1 1 d . . . . .
H10 H 1.167922 0.568544 0.511643 0.030 Uiso 1 1 calc R . . . .
C11 C 1.0671(2) 0.58019(13) 0.61711(10) 0.0254(4) Uani 1 1 d . . . . .
H11 H 1.150107 0.622237 0.636270 0.031 Uiso 1 1 calc R . . . .
C12 C 0.9311(2) 0.54919(12) 0.66279(10) 0.0223(3) Uani 1 1 d . . . . .
H12 H 0.922902 0.570591 0.712732 0.027 Uiso 1 1 calc R . . . .
C13 C 0.6854(2) 0.37737(11) 0.52845(9) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.4990(2) 0.41615(12) 0.53163(9) 0.0199(3) Uani 1 1 d . . . . .
H14A H 0.469277 0.431018 0.583288 0.030 Uiso 1 1 calc GR . . . .
H14B H 0.420742 0.368297 0.512354 0.030 Uiso 1 1 calc GR . . . .
H14C H 0.490522 0.473347 0.501235 0.030 Uiso 1 1 calc GR . . . .
C15 C 0.7214(2) 0.35083(13) 0.44497(9) 0.0246(4) Uani 1 1 d . . . . .
H15A H 0.636325 0.305284 0.427892 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.834761 0.322911 0.440837 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.715452 0.407759 0.414149 0.037 Uiso 1 1 calc GR . . . .
C16 C 0.7018(2) 0.28402(12) 0.57531(9) 0.0221(3) Uani 1 1 d . . . . .
H16A H 0.629099 0.235175 0.553591 0.033 Uiso 1 1 calc GR . . . .
H16B H 0.666549 0.296138 0.626738 0.033 Uiso 1 1 calc GR . . . .
H16C H 0.820103 0.262613 0.574778 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.2267(2) 0.56274(13) 0.82653(10) 0.0264(4) Uani 1 1 d . . . . .
H17A H 0.143286 0.514259 0.813412 0.040 Uiso 1 1 calc GR . . . .
H17B H 0.226885 0.612087 0.788337 0.040 Uiso 1 1 calc GR . . . .
H17C H 0.196983 0.590437 0.874776 0.040 Uiso 1 1 calc GR . . . .
C18 C 0.1664(2) 0.30300(14) 0.73068(11) 0.0293(4) Uani 1 1 d . . . . .
H18A H 0.057431 0.276537 0.746708 0.044 Uiso 1 1 calc GR . . . .
H18B H 0.229355 0.255499 0.702277 0.044 Uiso 1 1 calc GR . . . .
H18C H 0.146102 0.358372 0.699265 0.044 Uiso 1 1 calc GR . . . .
C19 C 0.4771(3) 0.19298(14) 0.91024(11) 0.0325(4) Uani 1 1 d . . . . .
H19A H 0.356340 0.208901 0.906663 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.524252 0.219917 0.956025 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.490317 0.124266 0.911148 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4249(19) . ?
O1 C7 1.3832(19) . ?
O2 C2 1.4266(18) . ?
O2 C17 1.414(2) . ?
O3 C3 1.421(2) . ?
O3 C18 1.417(2) . ?
O4 C4 1.4284(18) . ?
O4 C19 1.422(2) . ?
O5 C1 1.4038(19) . ?
O5 C5 1.4450(18) . ?
C1 H1 0.9800 . ?
C1 C2 1.522(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.528(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.516(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.531(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.511(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.413(2) . ?
C7 C12 1.386(2) . ?
C8 C9 1.398(2) . ?
C8 C13 1.536(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.538(2) . ?
C13 C15 1.540(2) . ?
C13 C16 1.542(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C7 O1 C1 119.86(12) . . ?
C17 O2 C2 113.78(13) . . ?
C18 O3 C3 112.90(13) . . ?
C19 O4 C4 113.59(13) . . ?
C1 O5 C5 115.12(12) . . ?
O1 C1 H1 109.3 . . ?
O1 C1 C2 104.75(12) . . ?
O5 C1 O1 112.41(13) . . ?
O5 C1 H1 109.3 . . ?
O5 C1 C2 111.76(13) . . ?
C2 C1 H1 109.3 . . ?
O2 C2 C1 106.53(13) . . ?
O2 C2 H2 110.1 . . ?
O2 C2 C3 110.57(13) . . ?
C1 C2 H2 110.1 . . ?
C1 C2 C3 109.36(13) . . ?
C3 C2 H2 110.1 . . ?
O3 C3 C2 112.10(13) . . ?
O3 C3 H3 108.8 . . ?
O3 C3 C4 108.93(13) . . ?
C2 C3 H3 108.8 . . ?
C4 C3 C2 109.44(13) . . ?
C4 C3 H3 108.8 . . ?
O4 C4 C3 109.99(13) . . ?
O4 C4 H4 110.0 . . ?
O4 C4 C5 106.37(12) . . ?
C3 C4 H4 110.0 . . ?
C3 C4 C5 110.46(13) . . ?
C5 C4 H4 110.0 . . ?
O5 C5 C4 111.60(12) . . ?
O5 C5 H5 108.9 . . ?
O5 C5 C6 106.05(13) . . ?
C4 C5 H5 108.9 . . ?
C6 C5 C4 112.50(13) . . ?
C6 C5 H5 108.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 115.84(14) . . ?
O1 C7 C12 122.34(14) . . ?
C12 C7 C8 121.82(15) . . ?
C7 C8 C13 121.73(14) . . ?
C9 C8 C7 116.22(15) . . ?
C9 C8 C13 122.03(14) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.39(16) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.05(16) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.38(16) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 120.13(16) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C8 C13 C14 111.77(13) . . ?
C8 C13 C15 111.89(14) . . ?
C8 C13 C16 108.68(13) . . ?
C14 C13 C15 106.69(13) . . ?
C14 C13 C16 110.61(13) . . ?
C15 C13 C16 107.10(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_date_sample_data_collection 2019-10-24
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.878
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2059246'
loop_
_audit_author_name
_audit_author_address
'Nathan Schley' 'Vanderbilt University'
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
'S-5 (2?-isopropylphenyl)-2,3,4-tri-O-methyl-α-L-rhamnopyranoside'
_chemical_formula_moiety         'C18 H28 O5'
_chemical_formula_sum            'C18 H28 O5'
_chemical_formula_weight         324.40
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H28O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.72846(11)
_cell_length_b                   13.3986(2)
_cell_length_c                   17.3987(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1801.64(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9748
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.2130
_cell_measurement_theta_min      4.1400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 11 0.0701
2 5 -9 0.0255
0 -8 4 0.0665
5 -1 1 0.0515
1 4 -10 0.0301
-4 -4 -3 0.1065
-4 3 -4 0.1246
2 7 -4 0.0717
-1 9 0 0.1251

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.116
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 -1.0000 11.0000 0.8193 0.6656 0.0837
2.0000 5.0000 -9.0000 -0.7230 -0.6649 0.3996
-0.0000 -8.0000 4.0000 0.1518 0.5877 -0.7764
5.0000 -1.0002 1.0000 -0.8302 0.5635 0.0871
1.0000 4.0000 -10.0000 -0.5944 -0.7925 0.2324
-4.0000 -3.9998 -3.0000 0.5572 -0.4370 -0.6449
-4.0000 3.0001 -4.0000 0.5321 -0.7671 0.0939
2.0000 6.9999 -4.0000 -0.5026 -0.3698 0.7364
-1.0000 9.0000 -0.0000 0.1971 -0.4204 0.9460

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.340
_diffrn_reflns_theta_min         4.165
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00 120.00   84
  2  ω   -106.00 -18.00   1.00    1.00    --  -37.09 -38.00-150.00   88
  3  ω   -104.00 -20.00   1.00    1.00    --  -37.09 -57.00 -60.00   84
  4  ω    -54.00  30.00   1.00    1.00    --  -37.09  57.00 -90.00   84
  5  ω     23.00  90.00   1.00    1.00    --   37.09-125.00-120.00   67
  6  ω     20.00 104.00   1.00    1.00    --   37.09  57.00 120.00   84
  7  ω     43.00 128.00   1.00    2.05    --  111.00 -45.00   0.00   85
  8  ω    100.00 178.00   1.00    2.05    --  111.00 111.00 -60.00   78
  9  ω     94.00 178.00   1.00    2.05    --  111.00  45.00  30.00   84
 10  ω     44.00 129.00   1.00    2.05    --  111.00 -61.00-180.00   85
 11  ω     93.00 178.00   1.00    2.05    --  111.00  61.00 -30.00   85
 12  ω     41.00 116.00   1.00    2.05    --  111.00-111.00 -30.00   75
 13  ω     57.00 150.00   1.00    2.05    --  111.00 178.00 120.00   93
 14  ω     43.00 138.00   1.00    2.05    --  111.00 -77.00   0.00   95
 15  ω    -54.00  30.00   1.00    1.00    --  -37.09  57.00  30.00   84
 16  ω    -90.00  -2.00   1.00    1.00    --  -37.09 125.00  60.00   88
 17  ω   -105.00 -10.00   1.00    1.00    --  -37.09 -77.00-150.00   95
 18  ω   -106.00 -18.00   1.00    1.00    --  -37.09 -38.00   0.00   88
 19  ω     73.00 135.00   1.00    2.05    --  111.00  15.00 -90.00   62
 20  ω     73.00 178.00   1.00    2.05    --  111.00  15.00 150.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1741465000
_diffrn_orient_matrix_UB_12      0.0025539000
_diffrn_orient_matrix_UB_13      0.0430487000
_diffrn_orient_matrix_UB_21      0.0906314000
_diffrn_orient_matrix_UB_22      -0.0366371000
_diffrn_orient_matrix_UB_23      0.0736591000
_diffrn_orient_matrix_UB_31      0.0344614000
_diffrn_orient_matrix_UB_32      0.1089350000
_diffrn_orient_matrix_UB_33      0.0237774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3437
_reflns_number_total             3583
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3583
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.5386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          
'Disorder in the isopropyl group was modeled with a similarity restraint placed on the thermal parameters of the partially occupied atoms.,Two-site disorder in the isopropyl group (54:46) was modeled with a similarity restraint placed on the thermal parameters of the partially occupied atoms.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C15 \\sim C15A: within 3A with sigma of 0.01 and sigma for terminal atoms of
0.02
3. Others
 Sof(H13A)=Sof(C15A)=Sof(H15F)=Sof(H15D)=Sof(H15E)=1-FVAR(1)
 Sof(H13)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C13(H13A)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C15A(H15F,H15D,H15E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3412(2) 0.54487(14) 0.67223(9) 0.0396(4) Uani 1 1 d . . . . .
O2 O 0.6194(2) 0.47199(17) 0.82709(10) 0.0522(5) Uani 1 1 d . . . . .
O3 O 0.7411(2) 0.67065(17) 0.79620(9) 0.0467(5) Uani 1 1 d . . . . .
O4 O 0.4379(2) 0.76714(13) 0.85064(9) 0.0386(4) Uani 1 1 d . . . . .
O5 O 0.2678(2) 0.51934(13) 0.80203(9) 0.0351(4) Uani 1 1 d . . . . .
C1 C 0.3810(3) 0.4941(2) 0.74217(13) 0.0375(5) Uani 1 1 d . . . . .
H1 H 0.376887 0.421893 0.733498 0.045 Uiso 1 1 calc R . . . .
C2 C 0.5669(3) 0.5253(2) 0.76033(13) 0.0390(6) Uani 1 1 d . . . . .
H2 H 0.642833 0.508691 0.717079 0.047 Uiso 1 1 calc R . . . .
C3 C 0.5727(3) 0.6365(2) 0.77595(12) 0.0359(5) Uani 1 1 d . . . . .
H3 H 0.534987 0.671913 0.729610 0.043 Uiso 1 1 calc R . . . .
C4 C 0.4496(3) 0.66150(18) 0.84096(12) 0.0323(5) Uani 1 1 d . . . . .
H4 H 0.490314 0.630652 0.888731 0.039 Uiso 1 1 calc R . . . .
C5 C 0.2674(3) 0.62404(18) 0.82213(12) 0.0321(5) Uani 1 1 d . . . . .
H5 H 0.222236 0.662348 0.778555 0.039 Uiso 1 1 calc R . . . .
C6 C 0.1442(3) 0.6347(2) 0.88907(14) 0.0385(5) Uani 1 1 d . . . . .
H6A H 0.031798 0.610849 0.874356 0.058 Uiso 1 1 calc GR . . . .
H6B H 0.136307 0.703674 0.903573 0.058 Uiso 1 1 calc GR . . . .
H6C H 0.186054 0.596325 0.931788 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.1980(3) 0.51580(18) 0.63004(13) 0.0342(5) Uani 1 1 d . . . . .
C8 C 0.1871(3) 0.55918(18) 0.55705(13) 0.0363(5) Uani 1 1 d . . . . .
C9 C 0.0468(4) 0.5315(2) 0.51123(15) 0.0481(7) Uani 1 1 d . . . . .
H9 H 0.036600 0.558453 0.462180 0.058 Uiso 1 1 calc R . . . .
C10 C -0.0761(4) 0.4658(2) 0.53651(17) 0.0526(8) Uani 1 1 d . . . . .
H10 H -0.168067 0.448747 0.504637 0.063 Uiso 1 1 calc R . . . .
C11 C -0.0644(4) 0.4244(2) 0.60926(17) 0.0503(7) Uani 1 1 d . . . . .
H11 H -0.148686 0.380195 0.626480 0.060 Uiso 1 1 calc R . . . .
C12 C 0.0748(3) 0.4497(2) 0.65654(15) 0.0446(6) Uani 1 1 d . . . . .
H12 H 0.084349 0.422173 0.705439 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3236(4) 0.63317(19) 0.53120(13) 0.0421(6) Uani 1 1 d . . . . .
H13 H 0.333765 0.686682 0.569333 0.051 Uiso 0.678(7) 1 calc R . P A 1
H13A H 0.441793 0.607604 0.536743 0.051 Uiso 0.322(7) 1 calc R . P A 2
C14 C 0.2895(6) 0.6778(3) 0.45328(18) 0.0798(12) Uani 1 1 d . . . . .
H14A H 0.276309 0.625324 0.416170 0.120 Uiso 1 1 calc GR . . . .
H14B H 0.384878 0.719676 0.438828 0.120 Uiso 1 1 calc GR . . . .
H14C H 0.185441 0.716880 0.455133 0.120 Uiso 1 1 calc GR . . . .
C15 C 0.5075(5) 0.5811(3) 0.5198(2) 0.0425(11) Uani 0.678(7) 1 d . U P A 1
H15A H 0.544748 0.552527 0.567563 0.064 Uiso 0.678(7) 1 calc GR . P A 1
H15B H 0.590318 0.630002 0.503149 0.064 Uiso 0.678(7) 1 calc GR . P A 1
H15C H 0.498137 0.529580 0.481670 0.064 Uiso 0.678(7) 1 calc GR . P A 1
C16 C 0.7572(6) 0.4100(4) 0.81905(19) 0.0945(17) Uani 1 1 d . . . . .
H16A H 0.735111 0.363506 0.778210 0.142 Uiso 1 1 calc GR . . . .
H16B H 0.775473 0.374118 0.866132 0.142 Uiso 1 1 calc GR . . . .
H16C H 0.858534 0.448430 0.807121 0.142 Uiso 1 1 calc GR . . . .
C17 C 0.8413(3) 0.6967(2) 0.73214(14) 0.0409(6) Uani 1 1 d . . . . .
H17A H 0.862368 0.638470 0.701432 0.061 Uiso 1 1 calc GR . . . .
H17B H 0.949607 0.724112 0.749047 0.061 Uiso 1 1 calc GR . . . .
H17C H 0.780565 0.745533 0.702055 0.061 Uiso 1 1 calc GR . . . .
C18 C 0.5199(4) 0.8023(2) 0.91835(16) 0.0478(6) Uani 1 1 d . . . . .
H18A H 0.641808 0.789012 0.915478 0.072 Uiso 1 1 calc GR . . . .
H18B H 0.471995 0.768859 0.962253 0.072 Uiso 1 1 calc GR . . . .
H18C H 0.501461 0.872897 0.923160 0.072 Uiso 1 1 calc GR . . . .
C15A C 0.2851(12) 0.7233(5) 0.5848(5) 0.043(2) Uani 0.322(7) 1 d . U P A 2
H15F H 0.296219 0.702823 0.637469 0.064 Uiso 0.322(7) 1 calc GR . P A 2
H15D H 0.169462 0.746686 0.575765 0.064 Uiso 0.322(7) 1 calc GR . P A 2
H15E H 0.365791 0.776045 0.574350 0.064 Uiso 0.322(7) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.428(3) . ?
O1 C7 1.384(3) . ?
O2 C2 1.422(3) . ?
O2 C16 1.358(4) . ?
O3 C3 1.424(3) . ?
O3 C17 1.401(3) . ?
O4 C4 1.428(3) . ?
O4 C18 1.418(3) . ?
O5 C1 1.402(3) . ?
O5 C5 1.446(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.529(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.516(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.516(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.530(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.512(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.399(3) . ?
C7 C12 1.380(4) . ?
C8 C9 1.396(3) . ?
C8 C13 1.516(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 H13A 0.9800 . ?
C13 C14 1.505(4) . ?
C13 C15 1.595(5) . ?
C13 C15A 1.555(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15A H15F 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?

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
C7 O1 C1 119.38(19) . . ?
C16 O2 C2 116.5(2) . . ?
C17 O3 C3 112.85(18) . . ?
C18 O4 C4 113.51(19) . . ?
C1 O5 C5 114.51(18) . . ?
O1 C1 H1 109.4 . . ?
O1 C1 C2 104.41(19) . . ?
O5 C1 O1 112.58(19) . . ?
O5 C1 H1 109.4 . . ?
O5 C1 C2 111.54(19) . . ?
C2 C1 H1 109.4 . . ?
O2 C2 C1 107.5(2) . . ?
O2 C2 H2 110.0 . . ?
O2 C2 C3 109.8(2) . . ?
C1 C2 H2 110.0 . . ?
C3 C2 C1 109.5(2) . . ?
C3 C2 H2 110.0 . . ?
O3 C3 C2 112.8(2) . . ?
O3 C3 H3 108.7 . . ?
O3 C3 C4 108.53(18) . . ?
C2 C3 H3 108.7 . . ?
C4 C3 C2 109.42(19) . . ?
C4 C3 H3 108.7 . . ?
O4 C4 C3 110.30(19) . . ?
O4 C4 H4 109.8 . . ?
O4 C4 C5 106.98(18) . . ?
C3 C4 H4 109.8 . . ?
C3 C4 C5 110.19(18) . . ?
C5 C4 H4 109.8 . . ?
O5 C5 C4 111.61(18) . . ?
O5 C5 H5 108.8 . . ?
O5 C5 C6 106.22(18) . . ?
C4 C5 H5 108.8 . . ?
C6 C5 C4 112.59(19) . . ?
C6 C5 H5 108.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 114.4(2) . . ?
C12 C7 O1 123.7(2) . . ?
C12 C7 C8 121.9(2) . . ?
C7 C8 C13 119.9(2) . . ?
C9 C8 C7 117.1(3) . . ?
C9 C8 C13 123.0(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 119.4(3) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C8 C13 H13 109.5 . . ?
C8 C13 H13A 113.0 . . ?
C8 C13 C15 111.8(2) . . ?
C8 C13 C15A 101.3(4) . . ?
C14 C13 C8 113.9(3) . . ?
C14 C13 H13 109.5 . . ?
C14 C13 H13A 113.0 . . ?
C14 C13 C15 102.6(3) . . ?
C14 C13 C15A 101.4(4) . . ?
C15 C13 H13 109.5 . . ?
C15A C13 H13A 113.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C15A H15F 109.5 . . ?
C13 C15A H15D 109.5 . . ?
C13 C15A H15E 109.5 . . ?
H15F C15A H15D 109.5 . . ?
H15F C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?

_olex2_date_sample_data_collection 2019-11-15
_olex2_exptl_crystal_mounting_method 'Mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.763
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
