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

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

data_rr001
_database_code_depnum_ccdc_archive 'CCDC 1856945'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O2'
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C O H'
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                   5.52630(10)
_cell_length_b                   7.5880(2)
_cell_length_c                   31.5641(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1323.60(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7361
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7320
_cell_measurement_theta_min      5.5690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45f (Rigaku Oxford Diffraction, 2018)
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    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            8543
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         5.607
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  23.00   0.50    0.50    --    0.00 -82.00-144.00  192
  2  ω    -75.00   8.00   0.50    0.50    --    0.00 -43.00  -6.00  166
  3  ω      9.00  34.00   0.50    0.50    --    0.00  43.00 145.00   50
  4  ω    -92.00 -67.00   0.50    0.50    -- -100.00 110.00-133.00   50
  5  ω   -149.00-123.00   0.50    0.50    -- -100.00 -82.00-144.00   52
  6  ω    -76.00 -51.00   0.50    0.50    -- -100.00  43.00 145.00   50
  7  ω   -158.00-133.00   0.50    0.50    -- -100.00 -43.00  -6.00   50
  8  ω   -135.00-109.00   0.50    0.50    -- -100.00-110.00 132.00   52
  9  ω    105.00 130.00   0.50    0.50    --  106.00 110.00-133.00   50
 10  ω    106.00 131.00   0.50    0.50    --  106.00  82.00 -22.00   50
 11  ω     57.00  82.00   0.50    0.50    --  106.00 -82.00-144.00   50
 12  ω    152.00 178.00   0.50    0.50    --  106.00  43.00 145.00   52
 13  ω     16.00  42.00   0.50    0.50    --    0.00  77.00  60.00   52
 14  ω      2.00  31.00   0.50    0.50    --    0.00 -99.00   0.00   58
 15  ω    -57.00   7.00   0.50    0.50    --    0.00 -38.00 150.00  128
 16  ω    -72.00 -26.00   0.50    0.50    -- -100.00  30.00  60.00   92
 17  ω    -80.00 -26.00   0.50    0.50    -- -100.00  45.00-120.00  108
 18  ω    -71.00 -28.00   0.50    0.50    -- -100.00  30.00 -30.00   86
 19  ω    -70.00 -23.00   0.50    0.50    -- -100.00  30.00-150.00   94
 20  ω    -77.00 -26.00   0.50    0.50    -- -100.00  45.00 -90.00  102
 21  ω     30.00  57.00   0.50    0.50    --  106.00 -94.00  60.00   54
 22  ω     31.00  69.00   0.50    0.50    --  106.00 -45.00  30.00   76
 23  ω     31.00  61.00   0.50    0.50    --  106.00 -30.00  30.00   60
 24  ω     71.00 109.00   0.50    0.50    --  106.00 -94.00  60.00   76
 25  ω     70.00 108.00   0.50    0.50    --  106.00 -94.00-150.00   76
 26  ω     31.00  65.00   0.50    0.50    --  106.00 -94.00-150.00   68
 27  ω     36.00  72.00   0.50    0.50    --  106.00 -45.00 -90.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0278463000
_diffrn_orient_matrix_UB_12      0.0380591000
_diffrn_orient_matrix_UB_13      -0.0476948000
_diffrn_orient_matrix_UB_21      0.2418839000
_diffrn_orient_matrix_UB_22      0.1010171000
_diffrn_orient_matrix_UB_23      0.0003204000
_diffrn_orient_matrix_UB_31      0.1356902000
_diffrn_orient_matrix_UB_32      -0.1719560000
_diffrn_orient_matrix_UB_33      -0.0103772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                2552
_reflns_number_total             2588
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_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         0.205
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.069
_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)+(0.0482P)²+0.3399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C14(H14), C2(H2)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.1794(2) 0.65402(16) 0.79245(4) 0.0209(3) Uani 1 1 d . . . . .
O1 O 0.0448(3) 0.7688(2) 0.51398(4) 0.0276(3) Uani 1 1 d . . . . .
C13 C 0.2178(3) 0.6437(2) 0.74951(5) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.1301(3) 0.5520(2) 0.67821(5) 0.0180(3) Uani 1 1 d . . . . .
H11 H 0.031964 0.490317 0.659418 0.022 Uiso 1 1 calc R . . . .
C12 C 0.0717(3) 0.5526(2) 0.72144(5) 0.0182(3) Uani 1 1 d . . . . .
H12 H -0.063944 0.492297 0.731150 0.022 Uiso 1 1 calc R . . . .
C15 C 0.4756(3) 0.7314(2) 0.69198(5) 0.0190(3) Uani 1 1 d . . . . .
H15 H 0.611703 0.791355 0.682383 0.023 Uiso 1 1 calc R . . . .
C14 C 0.4213(3) 0.7336(2) 0.73471(5) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.519906 0.794768 0.753520 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3309(3) 0.6411(2) 0.66280(5) 0.0171(3) Uani 1 1 d . . . . .
C16 C -0.0354(3) 0.5741(2) 0.80828(5) 0.0229(4) Uani 1 1 d . . . . .
H16A H -0.173163 0.621376 0.793672 0.034 Uiso 1 1 calc GR . . . .
H16B H -0.049910 0.597824 0.838045 0.034 Uiso 1 1 calc GR . . . .
H16C H -0.027803 0.449041 0.803804 0.034 Uiso 1 1 calc GR . . . .
C3 C 0.2928(3) 0.5013(2) 0.58884(5) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.1121(3) 0.5253(2) 0.56082(5) 0.0211(4) Uani 1 1 d . . . . .
C9 C 0.3936(3) 0.6516(2) 0.61575(5) 0.0187(4) Uani 1 1 d . . . . .
H9 H 0.570324 0.644656 0.613726 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3202(3) 0.8323(2) 0.59771(5) 0.0214(4) Uani 1 1 d . . . . .
H8A H 0.361643 0.924285 0.617780 0.026 Uiso 1 1 calc R . . . .
H8B H 0.407654 0.854444 0.571609 0.026 Uiso 1 1 calc R . . . .
C7 C 0.0495(3) 0.8354(2) 0.58918(5) 0.0224(4) Uani 1 1 d . . . . .
H7A H -0.037573 0.809392 0.615122 0.027 Uiso 1 1 calc R . . . .
H7B H 0.001915 0.951946 0.579710 0.027 Uiso 1 1 calc R . . . .
C6 C -0.0160(3) 0.7003(2) 0.55553(5) 0.0216(4) Uani 1 1 d . . . . .
H6 H -0.190902 0.679736 0.556626 0.026 Uiso 1 1 calc R . . . .
C1 C 0.5779(4) 0.2875(3) 0.62229(6) 0.0280(4) Uani 1 1 d . . . . .
C5 C 0.0181(4) 0.3849(3) 0.53131(6) 0.0282(4) Uani 1 1 d . . . . .
H5A H 0.148957 0.339783 0.514511 0.042 Uiso 1 1 calc GR . . . .
H5B H -0.102960 0.434574 0.513056 0.042 Uiso 1 1 calc GR . . . .
H5C H -0.051715 0.290842 0.547586 0.042 Uiso 1 1 calc GR . . . .
C2 C 0.4100(3) 0.3290(2) 0.59386(6) 0.0248(4) Uani 1 1 d . . . . .
H2 H 0.362113 0.240275 0.575348 0.030 Uiso 1 1 calc R . . . .
H1 H -0.081(7) 0.779(5) 0.4995(11) 0.072(10) Uiso 1 1 d . . . . .
H1A H 0.639(5) 0.170(3) 0.6232(7) 0.032(6) Uiso 1 1 d . . . . .
H1B H 0.642(5) 0.370(3) 0.6438(8) 0.037(6) Uiso 1 1 d . . . . .


_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
O2 C13 1.3743(19) . ?
O2 C16 1.423(2) . ?
O1 C6 1.450(2) . ?
O1 H1 0.84(4) . ?
C13 C12 1.384(2) . ?
C13 C14 1.396(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(2) . ?
C11 C10 1.388(2) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.382(2) . ?
C15 C10 1.399(2) . ?
C14 H14 0.9300 . ?
C10 C9 1.527(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C3 C4 1.346(2) . ?
C3 C9 1.527(2) . ?
C3 C2 1.468(2) . ?
C4 C6 1.514(2) . ?
C4 C5 1.508(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.539(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.520(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.519(2) . ?
C6 H6 0.9800 . ?
C1 C2 1.329(3) . ?
C1 H1A 0.95(3) . ?
C1 H1B 0.99(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 H2 0.9300 . ?

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
C13 O2 C16 116.79(13) . . ?
C6 O1 H1 110(2) . . ?
O2 C13 C12 124.74(15) . . ?
O2 C13 C14 115.26(14) . . ?
C12 C13 C14 120.00(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.58(16) . . ?
C13 C12 C11 119.36(16) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C10 121.65(16) . . ?
C10 C15 H15 119.2 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.70(16) . . ?
C15 C14 H14 120.1 . . ?
C11 C10 C15 117.70(15) . . ?
C11 C10 C9 123.23(15) . . ?
C15 C10 C9 119.01(14) . . ?
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 . . ?
C4 C3 C9 122.33(16) . . ?
C4 C3 C2 121.26(17) . . ?
C2 C3 C9 116.36(15) . . ?
C3 C4 C6 122.55(16) . . ?
C3 C4 C5 124.46(17) . . ?
C5 C4 C6 112.98(15) . . ?
C10 C9 C3 114.77(14) . . ?
C10 C9 H9 106.7 . . ?
C10 C9 C8 110.27(13) . . ?
C3 C9 H9 106.7 . . ?
C3 C9 C8 111.30(13) . . ?
C8 C9 H9 106.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 C9 109.81(15) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C6 C7 C8 110.35(15) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
O1 C6 C4 107.81(14) . . ?
O1 C6 C7 109.61(15) . . ?
O1 C6 H6 108.5 . . ?
C4 C6 C7 113.76(14) . . ?
C4 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C2 C1 H1A 119.3(15) . . ?
C2 C1 H1B 124.2(15) . . ?
H1A C1 H1B 117(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C2 H2 116.8 . . ?
C1 C2 C3 126.33(18) . . ?
C1 C2 H2 116.8 . . ?

_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 1.612
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_mc003
_database_code_depnum_ccdc_archive 'CCDC 1856946'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 O'
_chemical_formula_sum            'C11 H16 O'
_chemical_formula_weight         164.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H16 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   22.7253(4)
_cell_length_b                   22.7253(4)
_cell_length_c                   7.5782(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3913.68(17)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6360
_cell_measurement_theta_min      3.8740
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45f (Rigaku Oxford Diffraction, 2018)
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    1.115
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10823
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.073
_diffrn_reflns_theta_min         3.890
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  31.00   0.50    1.41    --    0.00 -99.00-120.00   92
  2  ω    -77.00   7.00   0.50    1.41    --    0.00 -38.00 -30.00  168
  3  ω    -79.00   6.00   0.50    1.41    --    0.00 -17.00 175.00  170
  4  ω    138.00 174.00   0.50    5.64    --  106.00  15.00   0.00   72
  5  ω    104.00 135.00   0.50    5.64    --  106.00  15.00   0.00   62
  6  ω     40.00  66.00   0.50    5.64    --  106.00 -30.00-150.00   52
  7  ω     33.00  68.00   0.50    5.64    --  106.00 -45.00   0.00   70
  8  ω     31.00  66.00   0.50    5.64    --  106.00 -30.00  30.00   70
  9  ω     31.00  74.00   0.50    5.64    --  106.00 -45.00  30.00   86
 10  ω     31.00  60.00   0.50    5.64    --  106.00 -30.00 120.00   58
 11  ω     33.00  72.00   0.50    5.64    --  106.00 -45.00 120.00   78
 12  ω     35.00 135.00   0.50    5.64    --  106.00-150.00 172.00  200
 13  ω    -78.00 -48.00   0.50    5.64    -- -100.00  45.00  60.00   60
 14  ω   -112.00 -24.00   0.50    5.64    -- -100.00 111.00 153.00  176
 15  ω   -108.00 -33.00   0.50    5.64    -- -100.00 111.00 150.00  150
 16  ω   -175.00 -80.00   0.50    5.64    -- -100.00-123.00 -25.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0025809000
_diffrn_orient_matrix_UB_12      0.0650540000
_diffrn_orient_matrix_UB_13      0.0561698000
_diffrn_orient_matrix_UB_21      -0.0149869000
_diffrn_orient_matrix_UB_22      0.0177579000
_diffrn_orient_matrix_UB_23      -0.1909423000
_diffrn_orient_matrix_UB_31      -0.0660984000
_diffrn_orient_matrix_UB_32      -0.0066393000
_diffrn_orient_matrix_UB_33      0.0413164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1828
_reflns_number_total             2055
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_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         0.223
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.081
_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)+(0.0628P)²+4.5410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1431
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.21391(5) 0.45733(5) 0.37871(16) 0.0337(3) Uani 1 1 d . . . . .
C9 C 0.16485(7) 0.33582(7) 0.5843(2) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.15631(7) 0.39386(7) 0.5556(2) 0.0291(4) Uani 1 1 d . . . . .
C3 C 0.16226(7) 0.42087(7) 0.3739(2) 0.0300(4) Uani 1 1 d . . . . .
C6 C 0.18350(7) 0.29412(7) 0.4375(2) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.15792(7) 0.31076(7) 0.7620(2) 0.0339(4) Uani 1 1 d . . . . .
C1 C 0.14245(8) 0.43796(8) 0.6981(2) 0.0342(4) Uani 1 1 d . . . . .
C4 C 0.16718(8) 0.37643(8) 0.2259(2) 0.0338(4) Uani 1 1 d . . . . .
C7 C 0.13526(8) 0.25350(8) 0.3743(2) 0.0382(4) Uani 1 1 d . . . . .
C5 C 0.20926(8) 0.32759(8) 0.2794(2) 0.0359(4) Uani 1 1 d . . . . .
C11 C 0.16590(9) 0.25502(8) 0.8087(3) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.07917(9) 0.25644(9) 0.4127(3) 0.0466(5) Uani 1 1 d . . . . .
H1 H 0.2115(10) 0.4837(11) 0.295(4) 0.055(7) Uiso 1 1 d . . . . .
H11A H 0.1590(10) 0.2414(10) 0.936(3) 0.053(6) Uiso 1 1 d . . . . .
H11B H 0.1777(10) 0.2240(11) 0.722(4) 0.057(7) Uiso 1 1 d . . . . .
H8A H 0.0622(10) 0.2883(11) 0.492(3) 0.058(7) Uiso 1 1 d . . . . .
H8B H 0.0488(12) 0.2276(11) 0.365(3) 0.062(7) Uiso 1 1 d . . . . .
H3 H 0.1266(9) 0.4473(9) 0.352(3) 0.036(5) Uiso 1 1 d . . . . .
H4A H 0.1267(9) 0.3597(8) 0.202(3) 0.034(5) Uiso 1 1 d . . . . .
H6 H 0.2164(8) 0.2695(8) 0.490(3) 0.035(5) Uiso 1 1 d . . . . .
H4B H 0.1801(9) 0.3966(9) 0.119(3) 0.039(5) Uiso 1 1 d . . . . .
H5A H 0.2496(10) 0.3446(9) 0.316(3) 0.046(6) Uiso 1 1 d . . . . .
H1A H 0.1766(12) 0.4470(12) 0.770(4) 0.072(8) Uiso 1 1 d . . . . .
H5B H 0.2168(8) 0.3000(9) 0.180(3) 0.033(5) Uiso 1 1 d . . . . .
H10 H 0.1467(9) 0.3374(9) 0.857(3) 0.037(5) Uiso 1 1 d . . . . .
H1B H 0.1081(11) 0.4270(11) 0.773(4) 0.062(7) Uiso 1 1 d . . . . .
H7 H 0.1502(10) 0.2212(10) 0.291(3) 0.049(6) Uiso 1 1 d . . . . .
H1C H 0.1334(13) 0.4757(13) 0.650(4) 0.081(9) Uiso 1 1 d . . . . .


_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 C3 1.4373(18) . ?
O1 H1 0.88(3) . ?
C9 C2 1.351(2) . ?
C9 C6 1.522(2) . ?
C9 C10 1.470(2) . ?
C2 C3 1.513(2) . ?
C2 C1 1.506(2) . ?
C3 C4 1.513(2) . ?
C3 H3 1.02(2) . ?
C6 C7 1.511(2) . ?
C6 C5 1.535(2) . ?
C6 H6 1.01(2) . ?
C10 C11 1.328(2) . ?
C10 H10 0.97(2) . ?
C1 H1A 0.97(3) . ?
C1 H1B 1.00(3) . ?
C1 H1C 0.95(3) . ?
C4 C5 1.520(2) . ?
C4 H4A 1.01(2) . ?
C4 H4B 0.98(2) . ?
C7 C8 1.309(3) . ?
C7 H7 1.03(2) . ?
C5 H5A 1.03(2) . ?
C5 H5B 1.00(2) . ?
C11 H11A 1.02(3) . ?
C11 H11B 1.00(3) . ?
C8 H8A 1.02(3) . ?
C8 H8B 1.02(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.0(15) . . ?
C2 C9 C6 122.01(15) . . ?
C2 C9 C10 120.68(15) . . ?
C10 C9 C6 117.29(14) . . ?
C9 C2 C3 121.99(15) . . ?
C9 C2 C1 124.35(15) . . ?
C1 C2 C3 113.63(14) . . ?
O1 C3 C2 106.50(13) . . ?
O1 C3 C4 110.05(13) . . ?
O1 C3 H3 108.2(11) . . ?
C2 C3 C4 114.22(14) . . ?
C2 C3 H3 108.3(11) . . ?
C4 C3 H3 109.4(11) . . ?
C9 C6 C5 111.63(14) . . ?
C9 C6 H6 105.3(12) . . ?
C7 C6 C9 114.20(14) . . ?
C7 C6 C5 109.40(14) . . ?
C7 C6 H6 108.8(11) . . ?
C5 C6 H6 107.2(11) . . ?
C9 C10 H10 117.5(12) . . ?
C11 C10 C9 126.80(17) . . ?
C11 C10 H10 115.7(12) . . ?
C2 C1 H1A 112.2(16) . . ?
C2 C1 H1B 114.0(14) . . ?
C2 C1 H1C 111.8(18) . . ?
H1A C1 H1B 111(2) . . ?
H1A C1 H1C 101(2) . . ?
H1B C1 H1C 106(2) . . ?
C3 C4 C5 109.65(14) . . ?
C3 C4 H4A 108.5(11) . . ?
C3 C4 H4B 109.0(12) . . ?
C5 C4 H4A 110.3(11) . . ?
C5 C4 H4B 112.0(12) . . ?
H4A C4 H4B 107.4(16) . . ?
C6 C7 H7 113.1(12) . . ?
C8 C7 C6 127.22(17) . . ?
C8 C7 H7 119.7(13) . . ?
C6 C5 H5A 108.4(12) . . ?
C6 C5 H5B 110.1(11) . . ?
C4 C5 C6 109.26(14) . . ?
C4 C5 H5A 110.9(12) . . ?
C4 C5 H5B 111.5(11) . . ?
H5A C5 H5B 106.6(16) . . ?
C10 C11 H11A 121.2(13) . . ?
C10 C11 H11B 122.3(14) . . ?
H11A C11 H11B 116.5(19) . . ?
C7 C8 H8A 122.5(14) . . ?
C7 C8 H8B 123.2(14) . . ?
H8A C8 H8B 114(2) . . ?

_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.691
####################################################################### 
# 
# 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_MLC_LIT_DA2
_database_code_depnum_ccdc_archive 'CCDC 1856950'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H32 O8'
_chemical_formula_sum            'C24 H32 O8'
_chemical_formula_weight         448.49

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.47360(10)
_cell_length_b                   20.0163(2)
_cell_length_c                   8.26160(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.345(2)
_cell_angle_gamma                90
_cell_volume                     1134.71(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16547
_cell_measurement_theta_min      5.8380
_cell_measurement_theta_max      78.5250

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.813
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22974
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.418
_diffrn_reflns_theta_max         74.486
_diffrn_reflns_theta_full        74.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4646
_reflns_number_gt                4490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²+0.0767P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4646
_refine_ls_number_parameters     312
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1350(5) 0.27722(18) 1.0359(5) 0.0505(8) Uani 1 1 d . . . . .
H1A H 1.0926 0.2343 0.9758 0.076 Uiso 1 1 calc R U . . .
H1B H 1.2287 0.2694 1.1570 0.076 Uiso 1 1 calc R U . . .
H1C H 1.1968 0.3038 0.9727 0.076 Uiso 1 1 calc R U . . .
C2 C 0.8252(4) 0.32412(12) 0.8809(4) 0.0343(5) Uani 1 1 d . . . . .
C3 C 0.6577(3) 0.36177(12) 0.8978(3) 0.0306(5) Uani 1 1 d . . . . .
H3 H 0.6187 0.3357 0.9818 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4803(4) 0.36182(12) 0.7207(3) 0.0302(5) Uani 1 1 d . . . . .
H4 H 0.5261 0.3490 0.6265 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1816(4) 0.30550(13) 0.5816(4) 0.0388(6) Uani 1 1 d . . . . .
H5A H 0.0987 0.2690 0.5942 0.047 Uiso 1 1 calc R U . . .
H5B H 0.2124 0.2956 0.4781 0.047 Uiso 1 1 calc R U . . .
C6 C 0.0745(4) 0.37072(13) 0.5543(4) 0.0417(6) Uani 1 1 d . . . . .
H6A H -0.0479 0.3679 0.4473 0.050 Uiso 1 1 calc R U . . .
H6B H 0.0400 0.3797 0.6563 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3756(3) 0.42794(12) 0.6698(3) 0.0282(4) Uani 1 1 d . . . . .
C8 C 0.4544(3) 0.48733(11) 0.7300(3) 0.0268(4) Uani 1 1 d . . . . .
C9 C 0.6680(3) 0.49088(12) 0.8551(3) 0.0286(5) Uani 1 1 d . . . . .
C10 C 0.7974(4) 0.49491(13) 0.7506(4) 0.0350(5) Uani 1 1 d . . . . .
H10A H 0.7776 0.4550 0.6769 0.052 Uiso 1 1 calc R U . . .
H10B H 0.9344 0.4976 0.8325 0.052 Uiso 1 1 calc R U . . .
H10C H 0.7629 0.5347 0.6755 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7231(3) 0.43093(12) 0.9820(3) 0.0310(5) Uani 1 1 d . . . . .
H11 H 0.8686 0.4300 1.0406 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6487(4) 0.45089(13) 1.1226(3) 0.0346(5) Uani 1 1 d . . . . .
H12 H 0.7366 0.4319 1.2391 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3910(6) 0.43856(17) 1.2158(5) 0.0518(8) Uani 1 1 d . . . . .
H13A H 0.4862 0.4206 1.3269 0.078 Uiso 1 1 calc R U . . .
H13B H 0.2657 0.4158 1.1858 0.078 Uiso 1 1 calc R U . . .
H13C H 0.3744 0.4866 1.2290 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7079(3) 0.54786(12) 0.9892(3) 0.0317(5) Uani 1 1 d . . . . .
H14 H 0.8505 0.5581 1.0384 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5967(4) 0.61204(12) 0.9216(3) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.6441 0.6335 0.8380 0.037 Uiso 1 1 calc R U . . .
H15B H 0.6218 0.6430 1.0216 0.037 Uiso 1 1 calc R U . . .
C16 C 0.3780(3) 0.59967(11) 0.8292(3) 0.0284(5) Uani 1 1 d . . . . .
H16 H 0.3378 0.5766 0.9169 0.034 Uiso 1 1 calc R U . . .
C17 C 0.2557(4) 0.66266(12) 0.7742(3) 0.0306(5) Uani 1 1 d . . . . .
C18 C 0.3275(4) 0.72214(14) 0.7649(4) 0.0402(6) Uani 1 1 d . . . . .
H18A H 0.2438 0.7599 0.7305 0.048 Uiso 1 1 calc R U . . .
H18B H 0.4628 0.7272 0.7926 0.048 Uiso 1 1 calc R U . . .
C19 C 0.0425(4) 0.65353(13) 0.7312(4) 0.0378(6) Uani 1 1 d . . . . .
H19A H -0.0221 0.6972 0.7088 0.057 Uiso 1 1 calc R U . . .
H19B H 0.0255 0.6320 0.8306 0.057 Uiso 1 1 calc R U . . .
H19C H -0.0153 0.6255 0.6259 0.057 Uiso 1 1 calc R U . . .
C20 C 0.3313(3) 0.55054(11) 0.6715(3) 0.0275(5) Uani 1 1 d . . . . .
H20 H 0.1933 0.5361 0.6389 0.033 Uiso 1 1 calc R U . . .
C21 C 0.3356(3) 0.58447(11) 0.5098(3) 0.0293(5) Uani 1 1 d . . . . .
C22 C 0.1802(4) 0.58714(13) 0.3584(3) 0.0354(5) Uani 1 1 d . . . . .
H22 H 0.0654 0.5649 0.3523 0.042 Uiso 1 1 calc R U . . .
C23A C 0.3342(18) 0.6660(5) 0.2461(15) 0.044(2) Uani 0.488(11) 1 d . . P A 1
H23A H 0.3119 0.7063 0.3051 0.053 Uiso 0.488(11) 1 calc R U P A 1
H23B H 0.3424 0.6801 0.1344 0.053 Uiso 0.488(11) 1 calc R U P A 1
C24A C 0.5232(9) 0.6329(3) 0.3638(7) 0.0366(18) Uani 0.488(11) 1 d . . P A 1
H24A H 0.5454 0.5922 0.3062 0.044 Uiso 0.488(11) 1 calc R U P A 1
H24B H 0.6338 0.6638 0.3856 0.044 Uiso 0.488(11) 1 calc R U P A 1
C23B C 0.3603(15) 0.6427(5) 0.2345(13) 0.0355(17) Uani 0.512(11) 1 d . . P A 2
H23C H 0.3474 0.6778 0.1460 0.043 Uiso 0.512(11) 1 calc R U P A 2
H23D H 0.4341 0.6052 0.2126 0.043 Uiso 0.512(11) 1 calc R U P A 2
C24B C 0.4733(8) 0.6699(3) 0.4109(7) 0.0331(16) Uani 0.512(11) 1 d . . P A 2
H24C H 0.5979 0.6888 0.4164 0.040 Uiso 0.512(11) 1 calc R U P A 2
H24D H 0.3990 0.7056 0.4395 0.040 Uiso 0.512(11) 1 calc R U P A 2
O1 O 0.9679(3) 0.31288(11) 1.0390(3) 0.0414(5) Uani 1 1 d . . . . .
O2 O 0.8349(3) 0.30658(12) 0.7447(3) 0.0478(5) Uani 1 1 d . . . . .
O3 O 0.3561(3) 0.30941(9) 0.7353(2) 0.0346(4) Uani 1 1 d . . . . .
O4 O 0.1924(3) 0.42439(9) 0.5354(2) 0.0343(4) Uani 1 1 d . . . . .
O5 O 0.4584(3) 0.42800(10) 1.0793(2) 0.0383(4) Uani 1 1 d . . . . .
O6 O 0.6584(3) 0.52178(9) 1.1299(2) 0.0360(4) Uani 1 1 d . . . . .
O7 O 0.1739(3) 0.62001(11) 0.2090(2) 0.0426(5) Uani 1 1 d . . . . .
O8 O 0.5095(3) 0.61507(9) 0.5334(2) 0.0349(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.447(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.208(3) . ?
C2 O1 1.338(3) . ?
C2 C3 1.514(3) . ?
C3 C4 1.536(3) . ?
C3 C11 1.540(4) . ?
C3 H3 1.0000 . ?
C4 O3 1.437(3) . ?
C4 C7 1.510(3) . ?
C4 H4 1.0000 . ?
C5 O3 1.417(3) . ?
C5 C6 1.501(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.437(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.332(3) . ?
C7 O4 1.381(3) . ?
C8 C9 1.521(3) . ?
C8 C20 1.526(3) . ?
C9 C10 1.533(3) . ?
C9 C14 1.534(3) . ?
C9 C11 1.538(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.526(3) . ?
C11 H11 1.0000 . ?
C12 O5 1.399(3) . ?
C12 O6 1.421(3) . ?
C12 H12 1.0000 . ?
C13 O5 1.422(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O6 1.450(3) . ?
C14 C15 1.512(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.526(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.517(3) . ?
C16 C20 1.558(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.321(4) . ?
C17 C19 1.500(4) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.510(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.328(3) . ?
C21 O8 1.379(3) . ?
C22 O7 1.383(3) . ?
C22 H22 0.9500 . ?
C23A O7 1.444(13) . ?
C23A C24A 1.514(13) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A O8 1.488(5) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C23B O7 1.400(10) . ?
C23B C24B 1.469(12) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B O8 1.444(5) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.8(2) . . ?
O2 C2 C3 126.0(2) . . ?
O1 C2 C3 111.2(2) . . ?
C2 C3 C4 110.2(2) . . ?
C2 C3 C11 111.3(2) . . ?
C4 C3 C11 115.44(19) . . ?
C2 C3 H3 106.4 . . ?
C4 C3 H3 106.4 . . ?
C11 C3 H3 106.4 . . ?
O3 C4 C7 112.5(2) . . ?
O3 C4 C3 105.17(19) . . ?
C7 C4 C3 114.96(19) . . ?
O3 C4 H4 108.0 . . ?
C7 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
O3 C5 C6 109.5(2) . . ?
O3 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
O3 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O4 C6 C5 110.7(2) . . ?
O4 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 O4 119.8(2) . . ?
C8 C7 C4 125.1(2) . . ?
O4 C7 C4 114.7(2) . . ?
C7 C8 C9 119.0(2) . . ?
C7 C8 C20 120.0(2) . . ?
C9 C8 C20 121.0(2) . . ?
C8 C9 C10 110.23(19) . . ?
C8 C9 C14 112.14(19) . . ?
C10 C9 C14 112.4(2) . . ?
C8 C9 C11 110.6(2) . . ?
C10 C9 C11 111.5(2) . . ?
C14 C9 C11 99.50(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 103.56(19) . . ?
C12 C11 C3 115.7(2) . . ?
C9 C11 C3 116.23(19) . . ?
C12 C11 H11 106.9 . . ?
C9 C11 H11 106.9 . . ?
C3 C11 H11 106.9 . . ?
O5 C12 O6 111.5(2) . . ?
O5 C12 C11 111.1(2) . . ?
O6 C12 C11 105.4(2) . . ?
O5 C12 H12 109.6 . . ?
O6 C12 H12 109.6 . . ?
C11 C12 H12 109.6 . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 C15 108.9(2) . . ?
O6 C14 C9 105.83(19) . . ?
C15 C14 C9 116.36(19) . . ?
O6 C14 H14 108.5 . . ?
C15 C14 H14 108.5 . . ?
C9 C14 H14 108.5 . . ?
C14 C15 C16 111.7(2) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 114.5(2) . . ?
C17 C16 C20 111.44(18) . . ?
C15 C16 C20 111.18(19) . . ?
C17 C16 H16 106.4 . . ?
C15 C16 H16 106.4 . . ?
C20 C16 H16 106.4 . . ?
C18 C17 C19 120.9(2) . . ?
C18 C17 C16 123.8(2) . . ?
C19 C17 C16 115.3(2) . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C8 115.6(2) . . ?
C21 C20 C16 112.32(18) . . ?
C8 C20 C16 110.57(18) . . ?
C21 C20 H20 105.9 . . ?
C8 C20 H20 105.9 . . ?
C16 C20 H20 105.9 . . ?
C22 C21 O8 122.6(2) . . ?
C22 C21 C20 122.3(2) . . ?
O8 C21 C20 115.07(19) . . ?
C21 C22 O7 124.6(2) . . ?
C21 C22 H22 117.7 . . ?
O7 C22 H22 117.7 . . ?
O7 C23A C24A 110.0(7) . . ?
O7 C23A H23A 109.7 . . ?
C24A C23A H23A 109.7 . . ?
O7 C23A H23B 109.7 . . ?
C24A C23A H23B 109.7 . . ?
H23A C23A H23B 108.2 . . ?
O8 C24A C23A 108.3(6) . . ?
O8 C24A H24A 110.0 . . ?
C23A C24A H24A 110.0 . . ?
O8 C24A H24B 110.0 . . ?
C23A C24A H24B 110.0 . . ?
H24A C24A H24B 108.4 . . ?
O7 C23B C24B 114.6(7) . . ?
O7 C23B H23C 108.6 . . ?
C24B C23B H23C 108.6 . . ?
O7 C23B H23D 108.6 . . ?
C24B C23B H23D 108.6 . . ?
H23C C23B H23D 107.6 . . ?
O8 C24B C23B 106.8(5) . . ?
O8 C24B H24C 110.4 . . ?
C23B C24B H24C 110.4 . . ?
O8 C24B H24D 110.4 . . ?
C23B C24B H24D 110.4 . . ?
H24C C24B H24D 108.6 . . ?
C2 O1 C1 115.2(2) . . ?
C5 O3 C4 111.15(19) . . ?
C7 O4 C6 113.97(19) . . ?
C12 O5 C13 113.1(2) . . ?
C12 O6 C14 110.48(19) . . ?
C22 O7 C23B 109.9(4) . . ?
C22 O7 C23A 112.4(5) . . ?
C21 O8 C24B 109.5(3) . . ?
C21 O8 C24A 112.7(3) . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_mc002
_database_code_depnum_ccdc_archive 'CCDC 1856948'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_audit_creation_date             2018-03-29
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 F2 O'
_chemical_formula_sum            'C19 H18 F2 O'
_chemical_formula_weight         300.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H18 F2 O1'
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'
F F 0.0727 0.0534 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   26.8452(2)
_cell_length_b                   26.8452(2)
_cell_length_c                   11.23090(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7009.36(12)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    27203
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.8010
_cell_measurement_theta_min      4.3310
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45f (Rigaku Oxford Diffraction, 2018)
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    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2844
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41015
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.094
_diffrn_reflns_theta_min         3.293
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  31.00   0.50    0.50    --    0.00 -99.00 120.00   92
  2  ω    -20.00  45.00   0.50    0.50    --    0.00  77.00-180.00  130
  3  ω    -45.00  20.00   0.50    0.50    --    0.00 -77.00-120.00  130
  4  ω    -20.00  45.00   0.50    0.50    --    0.00  77.00   0.00  130
  5  ω    -15.00  31.00   0.50    0.50    --    0.00 -99.00 -30.00   92
  6  ω    -20.00  45.00   0.50    0.50    --    0.00  77.00  60.00  130
  7  ω    -15.00  31.00   0.50    0.50    --    0.00 -99.00 -60.00   92
  8  ω    -20.00  45.00   0.50    0.50    --    0.00  77.00 -90.00  130
  9  ω   -170.00 -86.00   0.50    0.50    -- -100.00 -61.00-106.04  168
 10  ω   -172.00 -81.00   0.50    0.50    -- -100.00 -74.00  29.15  182
 11  ω   -112.00 -24.00   0.50    0.50    -- -100.00 111.00  30.00  176
 12  ω   -169.00 -84.00   0.50    0.50    -- -100.00 -66.00-118.39  170
 13  ω   -120.00 -28.00   0.50    0.50    -- -100.00  77.00 -90.00  184
 14  ω   -133.00 -31.00   0.50    0.50    -- -100.00 146.00  33.35  204
 15  ω   -120.00 -28.00   0.50    0.50    -- -100.00  77.00 150.00  184
 16  ω   -175.00 -91.00   0.50    0.50    -- -100.00 -45.00 -30.00  168
 17  ω   -133.00 -31.00   0.50    0.50    -- -100.00 146.00-132.72  204
 18  ω   -114.00 -30.00   0.50    0.50    -- -100.00  61.00  60.00  168
 19  ω   -158.00 -43.00   0.50    0.50    -- -100.00 179.00 -60.00  230
 20  ω   -131.00 -30.00   0.50    0.50    -- -100.00 143.00  95.78  202
 21  ω   -114.00 -30.00   0.50    0.50    -- -100.00  61.00 150.00  168
 22  ω   -170.00 -85.00   0.50    0.50    -- -100.00 -63.00 115.56  170
 23  ω   -112.00 -24.00   0.50    0.50    -- -100.00 111.00-180.00  176
 24  ω    -72.00 -23.00   0.50    0.50    -- -100.00  30.00  30.00   98
 25  ω   -158.00 -43.00   0.50    0.50    -- -100.00 179.00-150.00  230
 26  ω     29.00  66.00   0.50    0.50    --  106.00 -30.00 120.00   74
 27  ω     30.00 109.00   0.50    0.50    --  106.00 -94.00 -30.00  158
 28  ω     29.00  66.00   0.50    0.50    --  106.00 -30.00  90.00   74
 29  ω     31.00  74.00   0.50    0.50    --  106.00 -45.00  60.00   86
 30  ω     30.00 112.00   0.50    0.50    --  106.00-111.00  30.00  164
 31  ω     30.00 112.00   0.50    0.50    --  106.00-111.00-120.00  164
 32  ω     30.00  74.00   0.50    0.50    --  106.00-111.00  90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0165362000
_diffrn_orient_matrix_UB_12      -0.0183259000
_diffrn_orient_matrix_UB_13      -0.1166402000
_diffrn_orient_matrix_UB_21      0.0489271000
_diffrn_orient_matrix_UB_22      0.0622838000
_diffrn_orient_matrix_UB_23      -0.0195535000
_diffrn_orient_matrix_UB_31      0.0414932000
_diffrn_orient_matrix_UB_32      -0.0132611000
_diffrn_orient_matrix_UB_33      0.0695166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3128
_reflns_number_total             3304
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_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         1.070
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.059
_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)+(0.0560P)²+11.4901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C16(H16), C18(H18), C9(H9), C10(H10), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.47062(4) 0.53117(4) -0.04168(7) 0.0342(2) Uani 1 1 d . . . . .
O1 O 0.39040(4) 0.61125(5) 0.65259(9) 0.0287(2) Uani 1 1 d . . . . .
F1 F 0.34570(5) 0.27492(4) 0.54824(11) 0.0498(3) Uani 1 1 d . . . . .
C14 C 0.38265(6) 0.51086(5) 0.27228(12) 0.0217(3) Uani 1 1 d . . . . .
C8 C 0.36817(6) 0.43763(6) 0.50885(12) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.37682(6) 0.49694(6) 0.49589(12) 0.0229(3) Uani 1 1 d . . . . .
C15 C 0.43981(6) 0.52373(6) 0.27295(12) 0.0245(3) Uani 1 1 d . . . . .
H15 H 0.458710 0.528193 0.346994 0.029 Uiso 1 1 calc R . . . .
C19 C 0.35591(6) 0.50439(6) 0.16210(12) 0.0260(3) Uani 1 1 d . . . . .
H19 H 0.316872 0.495272 0.159558 0.031 Uiso 1 1 calc R . . . .
C2 C 0.40739(6) 0.53881(6) 0.57525(12) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.34978(6) 0.50679(6) 0.38603(12) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.310159 0.472898 0.377696 0.027 Uiso 1 1 calc R . . . .
C17 C 0.44158(6) 0.52389(6) 0.06201(12) 0.0265(3) Uani 1 1 d . . . . .
C16 C 0.46981(6) 0.53020(6) 0.16777(13) 0.0269(3) Uani 1 1 d . . . . .
H16 H 0.508677 0.538740 0.169059 0.032 Uiso 1 1 calc R . . . .
C18 C 0.38533(6) 0.51105(6) 0.05624(13) 0.0285(3) Uani 1 1 d . . . . .
H18 H 0.366960 0.506814 -0.018387 0.034 Uiso 1 1 calc R . . . .
C9 C 0.31319(6) 0.38916(6) 0.50625(13) 0.0281(3) Uani 1 1 d . . . . .
H9 H 0.280713 0.393864 0.494840 0.034 Uiso 1 1 calc R . . . .
C5 C 0.34379(6) 0.56049(6) 0.40019(12) 0.0278(3) Uani 1 1 d . . . . .
H5A H 0.331352 0.569261 0.323870 0.033 Uiso 1 1 calc R . . . .
H5B H 0.314366 0.553420 0.461233 0.033 Uiso 1 1 calc R . . . .
C3 C 0.41947(6) 0.59977(6) 0.55810(12) 0.0267(3) Uani 1 1 d . . . . .
H3 H 0.461769 0.626416 0.567447 0.032 Uiso 1 1 calc R . . . .
C4 C 0.40137(7) 0.61098(6) 0.43733(13) 0.0301(3) Uani 1 1 d . . . . .
H4A H 0.398432 0.646267 0.441411 0.036 Uiso 1 1 calc R . . . .
H4B H 0.430874 0.617185 0.377147 0.036 Uiso 1 1 calc R . . . .
C10 C 0.30519(7) 0.33432(6) 0.52001(15) 0.0340(3) Uani 1 1 d . . . . .
H10 H 0.267649 0.301583 0.519590 0.041 Uiso 1 1 calc R . . . .
C11 C 0.35282(7) 0.32837(6) 0.53430(15) 0.0350(3) Uani 1 1 d . . . . .
C13 C 0.41477(7) 0.42899(7) 0.52247(15) 0.0346(3) Uani 1 1 d . . . . .
H13 H 0.452512 0.461427 0.523185 0.041 Uiso 1 1 calc R . . . .
C1 C 0.43176(7) 0.53030(7) 0.68931(14) 0.0360(4) Uani 1 1 d . . . . .
H1A H 0.412925 0.489160 0.707894 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.425016 0.550596 0.754248 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.473206 0.545603 0.679958 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.40792(7) 0.37461(7) 0.53501(17) 0.0398(4) Uani 1 1 d . . . . .
H12 H 0.440208 0.369385 0.543822 0.048 Uiso 1 1 calc R . . . .
H1 H 0.4071(9) 0.6511(10) 0.6653(19) 0.054(6) Uiso 1 1 d . . . . .


_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
F2 C17 1.3601(15) . ?
O1 C3 1.4389(16) . ?
F1 C11 1.3586(17) . ?
C14 C15 1.3941(18) . ?
C14 C19 1.3972(19) . ?
C14 C6 1.5253(18) . ?
C8 C7 1.4968(18) . ?
C8 C9 1.3972(19) . ?
C8 C13 1.390(2) . ?
C7 C2 1.3449(19) . ?
C7 C6 1.5203(18) . ?
C15 C16 1.3908(19) . ?
C19 C18 1.389(2) . ?
C2 C3 1.5132(19) . ?
C2 C1 1.507(2) . ?
C6 C5 1.5366(18) . ?
C17 C16 1.373(2) . ?
C17 C18 1.372(2) . ?
C9 C10 1.386(2) . ?
C5 C4 1.518(2) . ?
C3 C4 1.521(2) . ?
C10 C11 1.375(2) . ?
C11 C12 1.376(2) . ?
C13 C12 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 C14 C19 117.97(12) . . ?
C15 C14 C6 122.61(12) . . ?
C19 C14 C6 119.33(12) . . ?
C9 C8 C7 121.23(12) . . ?
C13 C8 C7 120.95(12) . . ?
C13 C8 C9 117.82(13) . . ?
C8 C7 C6 115.49(11) . . ?
C2 C7 C8 121.99(12) . . ?
C2 C7 C6 122.50(12) . . ?
C16 C15 C14 121.54(13) . . ?
C18 C19 C14 121.23(13) . . ?
C7 C2 C3 122.05(12) . . ?
C7 C2 C1 124.50(13) . . ?
C1 C2 C3 113.43(12) . . ?
C14 C6 C5 110.35(11) . . ?
C7 C6 C14 112.49(11) . . ?
C7 C6 C5 111.24(11) . . ?
F2 C17 C16 118.79(13) . . ?
F2 C17 C18 118.38(13) . . ?
C18 C17 C16 122.82(13) . . ?
C17 C16 C15 118.04(13) . . ?
C17 C18 C19 118.39(13) . . ?
C10 C9 C8 121.15(14) . . ?
C4 C5 C6 109.19(11) . . ?
O1 C3 C2 106.97(11) . . ?
O1 C3 C4 110.74(12) . . ?
C2 C3 C4 114.25(11) . . ?
C5 C4 C3 110.59(11) . . ?
C11 C10 C9 118.51(14) . . ?
F1 C11 C10 119.23(14) . . ?
F1 C11 C12 118.18(14) . . ?
C10 C11 C12 122.59(14) . . ?
C12 C13 C8 122.07(14) . . ?
C11 C12 C13 117.84(14) . . ?

_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 1.578
_oxdiff_exptl_absorpt_empirical_full_min 0.583
####################################################################### 
# 
# 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_MLC_LIT_ene2
_database_code_depnum_ccdc_archive 'CCDC 1856949'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 O9'
_chemical_formula_weight         464.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1125(4)
_cell_length_b                   8.0779(3)
_cell_length_c                   13.1558(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.011(2)
_cell_angle_gamma                90
_cell_volume                     1169.41(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9702
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.22

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            82913
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.563
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        28.331
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5843
_reflns_number_gt                5615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.109'
_computing_publication_material  WinGX
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.2021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5843
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0821
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.17777(18) 0.0674(3) 0.19908(19) 0.0322(5) Uani 1 1 d . . . . .
H1A H 1.2027 -0.0048 0.1459 0.048 Uiso 1 1 calc R U . . .
H1B H 1.1697 0.0018 0.2604 0.048 Uiso 1 1 calc R U . . .
H1C H 1.2392 0.1537 0.2165 0.048 Uiso 1 1 calc R U . . .
C2 C 1.01741(15) 0.2443(2) 0.22754(14) 0.0203(4) Uani 1 1 d . . . . .
C3 C 0.89655(15) 0.3201(2) 0.18291(13) 0.0157(3) Uani 1 1 d . . . . .
H3 H 0.8794 0.2880 0.1089 0.019 Uiso 1 1 calc R U . . .
C4 C 0.90778(15) 0.5095(2) 0.18884(13) 0.0160(3) Uani 1 1 d . . . . .
H4 H 0.9643 0.5383 0.2523 0.019 Uiso 1 1 calc R U . . .
C5 C 0.96351(17) 0.7292(2) 0.08799(15) 0.0233(4) Uani 1 1 d . . . . .
H5A H 1.0086 0.7591 0.0308 0.028 Uiso 1 1 calc R U . . .
H5B H 1.0030 0.7844 0.1511 0.028 Uiso 1 1 calc R U . . .
C6 C 0.83383(17) 0.7840(3) 0.06426(14) 0.0227(4) Uani 1 1 d . . . . .
H6A H 0.8309 0.9044 0.0500 0.027 Uiso 1 1 calc R U . . .
H6B H 0.7943 0.7259 0.0022 0.027 Uiso 1 1 calc R U . . .
C7 C 0.78742(14) 0.5950(2) 0.19411(12) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.70730(14) 0.5365(2) 0.25244(12) 0.0121(3) Uani 1 1 d . . . . .
C9 C 0.73534(14) 0.3712(2) 0.30692(12) 0.0134(3) Uani 1 1 d . . . . .
C10 C 0.81330(16) 0.3908(2) 0.41282(13) 0.0169(3) Uani 1 1 d . . . . .
H10A H 0.8880 0.4511 0.4050 0.025 Uiso 1 1 calc R U . . .
H10B H 0.8341 0.2812 0.4420 0.025 Uiso 1 1 calc R U . . .
H10C H 0.7673 0.4526 0.4587 0.025 Uiso 1 1 calc R U . . .
C11 C 0.79443(14) 0.2493(2) 0.23813(12) 0.0147(3) Uani 1 1 d . . . . .
H11 H 0.8298 0.1561 0.2827 0.018 Uiso 1 1 calc R U . . .
C12 C 0.68661(15) 0.1798(2) 0.16500(13) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.7015 0.0611 0.1492 0.021 Uiso 1 1 calc R U . . .
C13 C 0.57241(19) 0.2086(3) 0.00066(15) 0.0332(5) Uani 1 1 d . . . . .
H13A H 0.5728 0.2662 -0.0649 0.050 Uiso 1 1 calc R U . . .
H13B H 0.4940 0.2261 0.0251 0.050 Uiso 1 1 calc R U . . .
H13C H 0.5851 0.0899 -0.0089 0.050 Uiso 1 1 calc R U . . .
C14 C 0.61937(15) 0.2739(2) 0.31792(12) 0.0147(3) Uani 1 1 d . . . . .
H14 H 0.6387 0.1874 0.3721 0.018 Uiso 1 1 calc R U . . .
C15 C 0.51161(15) 0.3733(2) 0.34127(13) 0.0153(3) Uani 1 1 d . . . . .
H15A H 0.5301 0.4228 0.4105 0.018 Uiso 1 1 calc R U . . .
H15B H 0.4405 0.2994 0.3409 0.018 Uiso 1 1 calc R U . . .
C16 C 0.48101(14) 0.5111(2) 0.26159(13) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.4655 0.4572 0.1926 0.016 Uiso 1 1 calc R U . . .
C17 C 0.59037(14) 0.6302(2) 0.26059(12) 0.0121(3) Uani 1 1 d . . . . .
H17 H 0.5725 0.6953 0.1956 0.015 Uiso 1 1 calc R U . . .
C18 C 0.59935(14) 0.7583(2) 0.34811(12) 0.0128(3) Uani 1 1 d . . . . .
C19 C 0.72871(16) 0.7827(2) 0.50134(13) 0.0201(4) Uani 1 1 d . . . . .
H19A H 0.7852 0.7138 0.5485 0.024 Uiso 1 1 calc R U . . .
H19B H 0.6956 0.8720 0.5409 0.024 Uiso 1 1 calc R U . . .
C20 C 0.79063(15) 0.8523(2) 0.41537(14) 0.0188(3) Uani 1 1 d . . . . .
H20A H 0.8335 0.9571 0.4361 0.023 Uiso 1 1 calc R U . . .
H20B H 0.8492 0.7723 0.3932 0.023 Uiso 1 1 calc R U . . .
C21 C 0.47774(15) 0.8501(2) 0.34869(12) 0.0148(3) Uani 1 1 d . . . . .
H21 H 0.4861 0.9326 0.4059 0.018 Uiso 1 1 calc R U . . .
C22 C 0.37891(15) 0.7253(2) 0.36409(13) 0.0175(3) Uani 1 1 d . . . . .
H22A H 0.4004 0.6681 0.4307 0.021 Uiso 1 1 calc R U . . .
H22B H 0.3008 0.7836 0.3653 0.021 Uiso 1 1 calc R U . . .
C23 C 0.36561(15) 0.6002(2) 0.27844(13) 0.0164(3) Uani 1 1 d . . . . .
C24 C 0.25967(16) 0.5675(3) 0.22199(16) 0.0242(4) Uani 1 1 d . . . . .
O1 O 1.06183(12) 0.14374(18) 0.16122(11) 0.0248(3) Uani 1 1 d . . . . .
O2 O 1.06691(14) 0.2698(3) 0.31298(12) 0.0404(4) Uani 1 1 d . . . . .
O3 O 0.96478(11) 0.55439(17) 0.10196(10) 0.0207(3) Uani 1 1 d . . . . .
O4 O 0.76923(11) 0.74875(16) 0.14918(10) 0.0188(3) Uani 1 1 d . . . . .
O5 O 0.66739(11) 0.27223(18) 0.07429(9) 0.0217(3) Uani 1 1 d . . . . .
O6 O 0.58471(11) 0.19331(16) 0.21955(9) 0.0163(2) Uani 1 1 d . . . . .
O7 O 0.63321(11) 0.68447(16) 0.44651(9) 0.0157(2) Uani 1 1 d . . . . .
O8 O 0.69032(10) 0.87977(15) 0.33617(9) 0.0158(2) Uani 1 1 d . . . . .
O9 O 0.43984(11) 0.93183(16) 0.25439(10) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.490(3) 1.003(4) 0.244(2) 0.034(7) Uiso 1 1 d . . . . .
H24A H 0.183(2) 0.630(4) 0.2337(19) 0.031(7) Uiso 1 1 d . . . . .
H24B H 0.251(2) 0.489(4) 0.164(2) 0.033(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.452(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.198(2) . ?
C2 O1 1.336(2) . ?
C2 C3 1.517(2) . ?
C3 C4 1.536(3) . ?
C3 C11 1.540(2) . ?
C3 H3 1.0000 . ?
C4 O3 1.429(2) . ?
C4 C7 1.515(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.424(2) . ?
C5 C6 1.498(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.438(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.340(2) . ?
C7 O4 1.378(2) . ?
C8 C17 1.520(2) . ?
C8 C9 1.527(2) . ?
C9 C14 1.533(2) . ?
C9 C10 1.543(2) . ?
C9 C11 1.544(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.535(2) . ?
C11 H11 1.0000 . ?
C12 O5 1.399(2) . ?
C12 O6 1.427(2) . ?
C12 H12 1.0000 . ?
C13 O5 1.425(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O6 1.452(2) . ?
C14 C15 1.508(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.534(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C23 1.514(2) . ?
C16 C17 1.552(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.541(2) . ?
C17 H17 1.0000 . ?
C18 O7 1.4275(19) . ?
C18 O8 1.4328(19) . ?
C18 C21 1.542(2) . ?
C19 O7 1.436(2) . ?
C19 C20 1.512(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O8 1.433(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O9 1.416(2) . ?
C21 C22 1.525(2) . ?
C21 H21 1.0000 . ?
C22 C23 1.505(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.328(3) . ?
C24 H24A 1.02(3) . ?
C24 H24B 0.98(3) . ?
O9 H9 0.83(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 123.62(17) . . ?
O2 C2 C3 124.03(18) . . ?
O1 C2 C3 112.34(15) . . ?
C2 C3 C4 108.70(15) . . ?
C2 C3 C11 109.79(14) . . ?
C4 C3 C11 113.93(14) . . ?
C2 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C11 C3 H3 108.1 . . ?
O3 C4 C7 114.42(14) . . ?
O3 C4 C3 104.72(14) . . ?
C7 C4 C3 112.97(14) . . ?
O3 C4 H4 108.2 . . ?
C7 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
O3 C5 C6 108.18(16) . . ?
O3 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
O3 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
O4 C6 C5 110.45(14) . . ?
O4 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O4 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 O4 119.59(14) . . ?
C8 C7 C4 121.79(15) . . ?
O4 C7 C4 117.95(14) . . ?
C7 C8 C17 120.50(15) . . ?
C7 C8 C9 117.94(14) . . ?
C17 C8 C9 121.52(13) . . ?
C8 C9 C14 111.91(13) . . ?
C8 C9 C10 112.72(14) . . ?
C14 C9 C10 109.93(13) . . ?
C8 C9 C11 110.99(13) . . ?
C14 C9 C11 99.22(13) . . ?
C10 C9 C11 111.32(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 113.72(13) . . ?
C12 C11 C9 104.01(13) . . ?
C3 C11 C9 116.18(14) . . ?
C12 C11 H11 107.5 . . ?
C3 C11 H11 107.5 . . ?
C9 C11 H11 107.5 . . ?
O5 C12 O6 110.55(14) . . ?
O5 C12 C11 110.66(14) . . ?
O6 C12 C11 105.17(13) . . ?
O5 C12 H12 110.1 . . ?
O6 C12 H12 110.1 . . ?
C11 C12 H12 110.1 . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 C15 107.50(13) . . ?
O6 C14 C9 105.53(12) . . ?
C15 C14 C9 116.62(14) . . ?
O6 C14 H14 109.0 . . ?
C15 C14 H14 109.0 . . ?
C9 C14 H14 109.0 . . ?
C14 C15 C16 110.71(13) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C23 C16 C15 110.89(13) . . ?
C23 C16 C17 112.75(14) . . ?
C15 C16 C17 110.89(13) . . ?
C23 C16 H16 107.3 . . ?
C15 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C8 C17 C18 114.84(13) . . ?
C8 C17 C16 111.70(13) . . ?
C18 C17 C16 112.30(12) . . ?
C8 C17 H17 105.7 . . ?
C18 C17 H17 105.7 . . ?
C16 C17 H17 105.7 . . ?
O7 C18 O8 106.55(12) . . ?
O7 C18 C17 112.23(13) . . ?
O8 C18 C17 110.55(12) . . ?
O7 C18 C21 108.47(12) . . ?
O8 C18 C21 107.67(13) . . ?
C17 C18 C21 111.16(12) . . ?
O7 C19 C20 102.20(13) . . ?
O7 C19 H19A 111.3 . . ?
C20 C19 H19A 111.3 . . ?
O7 C19 H19B 111.3 . . ?
C20 C19 H19B 111.3 . . ?
H19A C19 H19B 109.2 . . ?
O8 C20 C19 102.26(13) . . ?
O8 C20 H20A 111.3 . . ?
C19 C20 H20A 111.3 . . ?
O8 C20 H20B 111.3 . . ?
C19 C20 H20B 111.3 . . ?
H20A C20 H20B 109.2 . . ?
O9 C21 C22 107.02(13) . . ?
O9 C21 C18 111.93(13) . . ?
C22 C21 C18 109.29(14) . . ?
O9 C21 H21 109.5 . . ?
C22 C21 H21 109.5 . . ?
C18 C21 H21 109.5 . . ?
C23 C22 C21 109.98(13) . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C22 122.63(16) . . ?
C24 C23 C16 121.77(17) . . ?
C22 C23 C16 115.59(14) . . ?
C23 C24 H24A 120.6(15) . . ?
C23 C24 H24B 122.9(15) . . ?
H24A C24 H24B 116(2) . . ?
C2 O1 C1 115.16(16) . . ?
C5 O3 C4 110.95(14) . . ?
C7 O4 C6 116.89(14) . . ?
C12 O5 C13 113.46(15) . . ?
C12 O6 C14 110.62(12) . . ?
C18 O7 C19 107.91(13) . . ?
C18 O8 C20 107.68(13) . . ?
C21 O9 H9 110.5(19) . . ?

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038



####################################################################### 
# 
# 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_MLC_LIT_dioxenecoupling
_database_code_depnum_ccdc_archive 'CCDC 1856947'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;

_audit_creation_date             2018-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 O5'
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.39
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   8.0320(3)
_cell_length_b                   6.3518(2)
_cell_length_c                   16.1371(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.7797(15)
_cell_angle_gamma                90
_cell_volume                     821.49(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16547
_cell_measurement_theta_min      5.8380
_cell_measurement_theta_max      78.5250
_exptl_absorpt_coefficient_mu    0.768
_exptl_crystal_description       block
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2951
_exptl_crystal_F_000             345.1788
_exptl_crystal_size_min          ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20223
_diffrn_reflns_theta_full        68.2754
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         2.74
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_reflns_Friedel_coverage         0.977
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2920
_reflns_number_total             2984
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1328
_refine_diff_density_min         -0.1242
_refine_diff_density_rms         0.0283
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_d_res_high            0.8298
_refine_ls_d_res_low             16.1020
_refine_ls_goodness_of_fit_ref   1.0956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.0956
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0620
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O -0.23489(11) -0.02179(14) 0.32337(6) 0.0267(2) Uani 1.000000 .
O2 O -0.74511(11) -0.08609(14) 0.10441(6) 0.0281(2) Uani 1.000000 .
H2 H -0.7569(11) 0.0452(3) 0.1064(10) 0.0422(3) Uiso 1.000000 GR
O3 O -0.24809(11) 0.48040(14) 0.15815(6) 0.0251(2) Uani 1.000000 .
O4 O -0.09417(11) 0.33373(15) 0.41352(6) 0.0309(2) Uani 1.000000 .
O5 O 0.04566(12) 0.29656(14) 0.09742(6) 0.0301(2) Uani 1.000000 .
C6 C -0.37942(14) 0.14293(18) 0.16412(7) 0.0195(2) Uani 1.000000 .
C7 C -0.62843(16) 0.1141(2) 0.36295(8) 0.0274(3) Uani 1.000000 .
C8 C -0.43741(15) 0.20356(19) 0.24928(8) 0.0203(2) Uani 1.000000 .
C9 C -0.29425(15) 0.1816(2) 0.31335(7) 0.0214(3) Uani 1.000000 .
C10 C -0.23314(16) 0.26697(18) 0.14186(7) 0.0201(3) Uani 1.000000 .
C11 C -0.09390(15) 0.1845(2) 0.11576(8) 0.0240(3) Uani 1.000000 .
H11 H -0.09036(15) 0.0360(2) 0.10922(8) 0.0288(3) Uiso 1.000000 R
C12 C -0.40300(16) -0.0641(2) 0.03017(8) 0.0246(3) Uani 1.000000 .
C13 C -0.44876(14) -0.0107(2) 0.11652(7) 0.0206(2) Uani 1.000000 .
C14 C -0.22587(15) 0.3459(2) 0.35393(8) 0.0249(3) Uani 1.000000 .
C15 C -0.61653(18) -0.0429(2) 0.41712(9) 0.0328(3) Uani 1.000000 .
C16 C -0.58785(15) -0.1445(2) 0.14702(8) 0.0229(3) Uani 1.000000 .
C17 C -0.07123(17) -0.0239(2) 0.36504(9) 0.0324(3) Uani 1.000000 .
C18 C -0.06505(19) 0.1210(3) 0.43925(9) 0.0343(3) Uani 1.000000 .
C19 C -0.59925(15) 0.0875(2) 0.27125(8) 0.0228(3) Uani 1.000000 .
C20 C -0.59669(16) -0.1388(2) 0.24088(8) 0.0236(3) Uani 1.000000 .
C21 C -0.08756(19) 0.5781(2) 0.16806(9) 0.0313(3) Uani 1.000000 .
C22 C 0.0137(2) 0.5199(2) 0.09606(10) 0.0345(3) Uani 1.000000 .
C23 C -0.67151(19) 0.3323(2) 0.38847(10) 0.0338(3) Uani 1.000000 .
H17a H -0.050(2) -0.171(3) 0.3813(11) 0.038(4) Uiso 1.000000 .
H8 H -0.4623(18) 0.349(3) 0.2476(9) 0.023(3) Uiso 1.000000 .
H12a H -0.503(2) -0.086(3) -0.0056(10) 0.026(3) Uiso 1.000000 .
H21a H -0.1037(19) 0.729(3) 0.1691(10) 0.027(4) Uiso 1.000000 .
H14 H -0.2630(18) 0.497(3) 0.3433(9) 0.022(3) Uiso 1.000000 .
H19 H -0.6900(17) 0.162(2) 0.2405(8) 0.016(3) Uiso 1.000000 .
H12b H -0.338(2) -0.197(3) 0.0322(11) 0.037(4) Uiso 1.000000 .
H15a H -0.589(2) -0.194(3) 0.4017(12) 0.044(5) Uiso 1.000000 .
H22a H 0.124(2) 0.590(3) 0.1007(10) 0.033(4) Uiso 1.000000 .
H15b H -0.633(2) -0.014(3) 0.4738(11) 0.033(4) Uiso 1.000000 .
H23a H -0.775(2) 0.374(3) 0.3583(10) 0.032(4) Uiso 1.000000 .
H18a H -0.152(2) 0.083(3) 0.4754(11) 0.036(4) Uiso 1.000000 .
H16 H -0.5673(16) -0.291(2) 0.1324(8) 0.015(3) Uiso 1.000000 .
H20a H -0.7024(19) -0.216(2) 0.2552(9) 0.022(4) Uiso 1.000000 .
H23b H -0.592(2) 0.438(3) 0.3738(11) 0.043(5) Uiso 1.000000 .
H23c H -0.681(2) 0.348(3) 0.4474(12) 0.045(5) Uiso 1.000000 .
H18b H 0.043(2) 0.116(3) 0.4703(10) 0.033(4) Uiso 1.000000 .
H20b H -0.5042(19) -0.214(2) 0.2648(9) 0.020(4) Uiso 1.000000 .
H17b H 0.011(2) 0.025(2) 0.3216(10) 0.030(4) Uiso 1.000000 .
H22b H -0.044(2) 0.555(3) 0.0432(11) 0.039(5) Uiso 1.000000 .
H21b H -0.026(2) 0.528(2) 0.2220(10) 0.030(4) Uiso 1.000000 .
H12c H -0.339(2) 0.054(3) 0.0077(10) 0.029(4) Uiso 1.000000 .


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 C9 1.3830(15) . ?
O1 C17 1.4366(16) . ?
O2 C16 1.4460(15) . ?
O3 C10 1.3876(15) . ?
O3 C21 1.4304(17) . ?
O4 C14 1.3840(15) . ?
O4 C18 1.4286(19) . ?
O5 C11 1.3763(15) . ?
O5 C22 1.4415(18) . ?
C6 C8 1.5291(16) . ?
C6 C10 1.4785(17) . ?
C6 C13 1.3403(17) . ?
C7 C15 1.325(2) . ?
C7 C19 1.5227(17) . ?
C7 C23 1.493(2) . ?
C8 C9 1.5013(16) . ?
C8 C19 1.5555(16) . ?
C9 C14 1.3312(19) . ?
C10 C11 1.3283(18) . ?
C12 C13 1.5031(16) . ?
C13 C16 1.5114(16) . ?
C16 C20 1.5214(17) . ?
C17 C18 1.508(2) . ?
C19 C20 1.5193(18) . ?
C21 C22 1.508(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O1 C9 111.16(10) . . ?
C21 O3 C10 110.88(11) . . ?
C18 O4 C14 110.97(10) . . ?
C22 O5 C11 111.44(10) . . ?
C10 C6 C8 112.22(10) . . ?
C13 C6 C8 123.97(10) . . ?
C13 C6 C10 123.76(11) . . ?
C19 C7 C15 123.26(13) . . ?
C23 C7 C15 121.64(13) . . ?
C23 C7 C19 115.10(12) . . ?
C9 C8 C6 109.31(9) . . ?
C19 C8 C6 113.21(10) . . ?
C19 C8 C9 114.37(10) . . ?
C8 C9 O1 114.18(10) . . ?
C14 C9 O1 123.16(11) . . ?
C14 C9 C8 122.58(12) . . ?
C6 C10 O3 113.23(10) . . ?
C11 C10 O3 122.03(11) . . ?
C11 C10 C6 124.48(11) . . ?
C10 C11 O5 125.39(11) . . ?
C12 C13 C6 125.29(11) . . ?
C16 C13 C6 120.72(11) . . ?
C16 C13 C12 113.97(10) . . ?
C9 C14 O4 124.72(13) . . ?
C13 C16 O2 110.02(10) . . ?
C20 C16 O2 111.75(10) . . ?
C20 C16 C13 113.26(10) . . ?
C18 C17 O1 110.32(12) . . ?
C17 C18 O4 110.49(11) . . ?
C8 C19 C7 110.70(10) . . ?
C20 C19 C7 115.12(11) . . ?
C20 C19 C8 110.21(10) . . ?
C19 C20 C16 110.25(10) . . ?
C22 C21 O3 109.61(12) . . ?
C21 C22 O5 109.51(12) . . ?


_olex2_date_sample_completion    2015-05-27
_olex2_date_sample_data_collection 2015-05-26
_olex2_date_sample_submission    2015-05-26
_olex2_submission_original_sample_id MLC-II-225
_olex2_submission_special_instructions 'No special instructions were received'
