# Electronic Supplementary Material (ESI) for ChemComm.
# 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_MM-XIV-9(exp_390)
_database_code_depnum_ccdc_archive 'CCDC 1895671'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Republic of Ireland
;
_audit_update_record             
;
2019-02-05 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H23 O5'
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                   6.80413(3)
_cell_length_b                   12.83725(7)
_cell_length_c                   22.67679(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.736(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    30382
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5360
_cell_measurement_theta_min      5.1880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0454
0 -1 -2 0.0180
0 1 2 0.0309
-1 1 -2 0.0735
2 -1 -2 0.0492
-1 0 -14 0.0481
-3 -1 -9 0.0813
0 7 9 0.0293

_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.049
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.0000 1.0000 -0.0402 -0.0010 -0.0547
-0.0000 -1.0000 -2.0002 0.0802 0.1219 0.1076
0.0000 1.0000 2.0002 -0.0802 -0.1219 -0.1076
-1.0000 1.0000 -1.9999 -0.1017 -0.1164 0.2454
2.0000 -1.0000 -2.0001 0.4451 0.1186 -0.1604
-1.3928 0.2068 -13.9653 0.3076 -0.0089 0.9515
-3.3505 -0.7788 -9.4945 -0.2297 0.1083 0.9672
0.0001 6.9999 9.0014 -0.3599 -0.8488 -0.4796

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43150
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.576
_diffrn_reflns_theta_min         3.899
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  96.00   1.00    0.50    --   48.91-125.00 -30.00   64
  2  ω     33.00 115.00   1.00    0.50    --   48.91  38.00 120.00   82
  3  ω    -55.00 -30.00   1.00    0.50    --  -49.16 -57.00-150.00   25
  4  ω    -65.00 -22.00   1.00    0.50    --  -49.16 -77.00-150.00   43
  5  ω    -50.00 -23.00   1.00    0.50    --  -49.16 -77.00  30.00   27
  6  ω    -78.00 -22.00   1.00    0.50    --  -49.16 -77.00 150.00   56
  7  ω    -57.00 -22.00   1.00    0.50    --  -49.16 -77.00  90.00   35
  8  ω    -48.00 -22.00   1.00    0.50    --  -49.16 -77.00 -30.00   26
  9  ω    -55.00 -28.00   1.00    0.50    --  -49.16 -57.00   0.00   27
 10  ω    -70.00  19.00   1.00    0.50    --  -49.16  57.00 120.00   89
 11  ω   -104.00 -29.00   1.00    0.50    --  -49.16 -19.00   0.00   75
 12  ω   -117.00 -85.00   1.00    0.50    --  -49.16 -77.00 150.00   32
 13  ω    -48.00 -22.00   1.00    0.50    --  -49.16 -77.00 -90.00   26
 14  ω   -110.00 -35.00   1.00    0.50    --  -49.16 -38.00 -60.00   75
 15  ω   -147.00-121.00   1.00    1.06    --  -82.50 -74.00 160.00   26
 16  ω    -87.00 -58.00   1.00    1.06    --  -82.50 -68.00  20.96   29
 17  ω    -95.00 -55.00   1.00    1.06    --  -82.50 -77.00-180.00   40
 18  ω    -82.00 -56.00   1.00    1.06    --  -82.50 -76.00  52.90   26
 19  ω    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00 120.00   27
 20  ω    -82.00 -56.00   1.00    1.06    --  -82.50 -74.00 160.00   26
 21  ω    -81.00 -55.00   1.00    1.06    --  -82.50 -78.00 150.38   26
 22  ω    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00   0.00   27
 23  ω    -81.00 -55.00   1.00    1.06    --  -82.50 -77.00-150.00   26
 24  ω    -81.00 -55.00   1.00    1.06    --  -82.50 -77.00 -30.00   26
 25  ω    -79.00 -54.00   1.00    1.06    --  -82.50 -80.00  23.59   25
 26  ω    -87.00 -56.00   1.00    1.06    --  -82.50 -75.00  68.71   31
 27  ω    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00 -90.00   27
 28  ω    -82.00 -55.00   1.00    1.06    --  -82.50 -77.00  90.00   27
 29  ω    -82.00 -55.00   1.00    1.06    --  -82.50 -79.00-103.47   27
 30  ω    -83.00 -57.00   1.00    1.06    --  -82.50 -76.00 134.06   26
 31  ω    -82.00 -57.00   1.00    1.06    --  -82.50 -70.00 -59.34   25
 32  ω   -112.00 -59.00   1.00    1.06    --  -82.50 -66.00-158.78   53
 33  ω    -83.00 -57.00   1.00    1.06    --  -82.50 -72.00 -75.95   26
 34  ω     74.00 155.00   1.00    1.06    --  100.40  77.00  90.00   81
 35  ω     74.00 160.00   1.00    1.06    --  100.40  77.00-150.00   86
 36  ω     76.00 159.00   1.00    1.06    --  100.40  77.00  30.00   83
 37  ω     73.00 121.00   1.00    1.06    --  100.40  77.00 -90.00   48
 38  ω     33.00  66.00   1.00    1.06    --  100.40 -61.00   0.00   33
 39  ω     37.00 108.00   1.00    1.06    --  100.40 -94.00  60.00   71
 40  ω     28.00  85.00   1.00    1.06    --  100.40 -94.00-120.00   57
 41  ω    107.00 154.00   1.00    1.06    --  100.40  77.00  60.00   47
 42  ω     75.00 102.00   1.00    1.06    --  100.40  77.00  60.00   27
 43  ω     74.00 149.00   1.00    1.06    --  100.40  77.00   0.00   75
 44  ω     75.00 153.00   1.00    1.06    --  100.40  77.00 -60.00   78
 45  ω     74.00 153.00   1.00    1.06    --  100.40  77.00-180.00   79
 46  ω     87.00 168.00   1.00    1.06    --  100.40  61.00 150.00   81
 47  ω     50.00 106.00   1.00    1.06    --  100.40 -94.00 150.00   56
 48  ω    121.00 167.00   1.00    1.06    --  100.40  62.00-106.25   46
 49  ω     36.00  66.00   1.00    1.06    --  100.40 -61.00-120.00   30
 50  ω     47.00 117.00   1.00    1.06    --  100.40-125.00 -30.00   70
 51  ω    129.00 168.00   1.00    1.06    --  100.40  77.00 120.00   39
 52  ω     38.00  64.00   1.00    1.06    --  100.40 -61.00  60.00   26
 53  ω     77.00 117.00   1.00    1.06    --  100.40  62.00-106.25   40
 54  ω     74.00 100.00   1.00    1.06    --  100.40  77.00 120.00   26
 55  ω     40.00  67.00   1.00    1.06    --  100.40 -61.00  90.00   27
 56  ω    126.00 160.00   1.00    1.06    --  100.40  77.00 -90.00   34
 57  ω     34.00 110.00   1.00    1.06    --  100.40 -94.00 -30.00   76
 58  ω     42.00  68.00   1.00    1.06    --  100.40 -61.00 150.00   26
 59  ω     76.00 151.00   1.00    1.06    --  100.40  77.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1824709000
_diffrn_orient_matrix_UB_12      0.0002966000
_diffrn_orient_matrix_UB_13      -0.0402215000
_diffrn_orient_matrix_UB_21      -0.0016613000
_diffrn_orient_matrix_UB_22      -0.1200057000
_diffrn_orient_matrix_UB_23      -0.0009728000
_diffrn_orient_matrix_UB_31      -0.1340005000
_diffrn_orient_matrix_UB_32      0.0018809000
_diffrn_orient_matrix_UB_33      -0.0547388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3953
_reflns_number_total             4041
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.044
_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)+(0.0381P)²+0.3410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0648
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.85492(16) 0.50301(9) 0.26077(5) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.45384(18) 0.41265(8) 0.21371(5) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.30341(16) 0.54152(8) 0.16462(5) 0.0242(2) Uani 1 1 d . . . . .
O4 O 0.71541(17) 0.61064(8) 0.13563(4) 0.0244(2) Uani 1 1 d . . . . .
O5 O 0.74532(16) 0.73625(8) 0.20453(4) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.7045(2) 0.54529(11) 0.27502(6) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.5542(2) 0.59149(11) 0.22992(6) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.4361(2) 0.50332(11) 0.20190(6) 0.0174(3) Uani 1 1 d . . . . .
C4 C 0.1709(3) 0.46641(13) 0.13806(8) 0.0279(3) Uani 1 1 d . . . . .
H4A H 0.080806 0.502406 0.111192 0.042 Uiso 1 1 calc GR . . . .
H4B H 0.095214 0.431433 0.169048 0.042 Uiso 1 1 calc GR . . . .
H4C H 0.247100 0.414658 0.116009 0.042 Uiso 1 1 calc GR . . . .
C5 C 0.6763(2) 0.64638(11) 0.18318(6) 0.0173(3) Uani 1 1 d . . . . .
C6 C 0.8849(3) 0.79101(14) 0.16776(8) 0.0323(4) Uani 1 1 d . . . . .
H6A H 0.988966 0.742963 0.155406 0.049 Uiso 1 1 calc GR . . . .
H6B H 0.942736 0.848728 0.190092 0.049 Uiso 1 1 calc GR . . . .
H6C H 0.817543 0.818455 0.132859 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.4161(2) 0.65795(11) 0.26891(6) 0.0154(3) Uani 1 1 d . . . . .
H7A H 0.467735 0.729526 0.273843 0.019 Uiso 1 1 calc R . . . .
H7B H 0.282320 0.661535 0.251869 0.019 Uiso 1 1 calc R . . . .
C8 C 0.41582(19) 0.59858(10) 0.32800(6) 0.0142(3) Uani 1 1 d . . . . .
H8 H 0.344096 0.531631 0.321281 0.017 Uiso 1 1 calc R . . . .
C9 C 0.3168(2) 0.65248(11) 0.37942(6) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.2925(2) 0.76046(11) 0.38186(6) 0.0184(3) Uani 1 1 d . . . . .
H10 H 0.341621 0.802771 0.350814 0.022 Uiso 1 1 calc R . . . .
C11 C 0.1965(2) 0.80666(12) 0.42958(6) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.180514 0.880148 0.430699 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1244(2) 0.74615(13) 0.47535(6) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.058206 0.777782 0.507602 0.027 Uiso 1 1 calc R . . . .
C13 C 0.1498(2) 0.63883(13) 0.47362(6) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.101795 0.596901 0.505000 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2453(2) 0.59248(11) 0.42607(6) 0.0185(3) Uani 1 1 d . . . . .
H14 H 0.261938 0.519015 0.425353 0.022 Uiso 1 1 calc R . . . .
C15 C 0.6371(2) 0.57044(10) 0.33786(6) 0.0146(3) Uani 1 1 d . . . . .
C16 C 0.7582(2) 0.66717(11) 0.35576(6) 0.0182(3) Uani 1 1 d . . . . .
H16A H 0.896826 0.647760 0.359759 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.709637 0.694110 0.393482 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.744871 0.721029 0.325392 0.027 Uiso 1 1 calc GR . . . .
C17 C 0.6663(2) 0.47868(10) 0.37915(6) 0.0154(3) Uani 1 1 d . . . . .
C18 C 0.6298(2) 0.37758(11) 0.35923(6) 0.0184(3) Uani 1 1 d . . . . .
H18 H 0.587574 0.366961 0.319755 0.022 Uiso 1 1 calc R . . . .
C19 C 0.6542(2) 0.29262(11) 0.39607(7) 0.0199(3) Uani 1 1 d . . . . .
H19 H 0.630430 0.224543 0.381283 0.024 Uiso 1 1 calc R . . . .
C20 C 0.7132(2) 0.30527(11) 0.45465(6) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.7397(2) 0.21143(12) 0.49397(8) 0.0289(4) Uani 1 1 d . . . . .
H21A H 0.618782 0.169982 0.494011 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.768919 0.234494 0.534226 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.848735 0.168896 0.479201 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.7453(2) 0.40587(12) 0.47495(6) 0.0214(3) Uani 1 1 d . . . . .
H22 H 0.782536 0.416533 0.514872 0.026 Uiso 1 1 calc R . . . .
C23 C 0.7238(2) 0.49156(11) 0.43766(6) 0.0184(3) Uani 1 1 d . . . . .
H23 H 0.748666 0.559590 0.452361 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2027(18) . ?
O2 C3 1.2005(18) . ?
O3 C3 1.3304(18) . ?
O3 C4 1.4510(18) . ?
O4 C5 1.2017(18) . ?
O5 C5 1.3364(17) . ?
O5 C6 1.4461(18) . ?
C1 C2 1.5632(19) . ?
C1 C15 1.5315(19) . ?
C2 C3 1.5267(19) . ?
C2 C5 1.5199(19) . ?
C2 C7 1.5467(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5417(18) . ?
C8 H8 1.0000 . ?
C8 C9 1.5140(18) . ?
C8 C15 1.5644(18) . ?
C9 C10 1.3972(19) . ?
C9 C14 1.396(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.5445(19) . ?
C15 C17 1.5178(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3964(19) . ?
C17 C23 1.393(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(2) . ?
C20 C21 1.510(2) . ?
C20 C22 1.388(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.395(2) . ?
C23 H23 0.9500 . ?

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 O3 C4 116.13(12) . . ?
C5 O5 C6 116.21(12) . . ?
O1 C1 C2 123.52(13) . . ?
O1 C1 C15 126.87(13) . . ?
C15 C1 C2 109.44(11) . . ?
C3 C2 C1 109.60(11) . . ?
C3 C2 C7 109.10(11) . . ?
C5 C2 C1 105.94(11) . . ?
C5 C2 C3 109.95(11) . . ?
C5 C2 C7 118.35(11) . . ?
C7 C2 C1 103.46(10) . . ?
O2 C3 O3 124.58(14) . . ?
O2 C3 C2 124.95(14) . . ?
O3 C3 C2 110.39(11) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 O5 125.22(14) . . ?
O4 C5 C2 124.74(13) . . ?
O5 C5 C2 109.86(11) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 111.2 . . ?
C2 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 C2 103.00(10) . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
C7 C8 H8 107.0 . . ?
C7 C8 C15 103.72(11) . . ?
C9 C8 C7 116.36(11) . . ?
C9 C8 H8 107.0 . . ?
C9 C8 C15 115.07(11) . . ?
C15 C8 H8 107.0 . . ?
C10 C9 C8 122.45(12) . . ?
C14 C9 C8 119.11(12) . . ?
C14 C9 C10 118.43(12) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.50(14) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.53(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.38(13) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.24(14) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 120.91(13) . . ?
C13 C14 H14 119.5 . . ?
C1 C15 C8 101.76(11) . . ?
C1 C15 C16 104.73(11) . . ?
C16 C15 C8 111.42(11) . . ?
C17 C15 C1 111.79(11) . . ?
C17 C15 C8 113.18(11) . . ?
C17 C15 C16 113.08(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 119.89(12) . . ?
C23 C17 C15 122.15(12) . . ?
C23 C17 C18 117.93(13) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.05(13) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.12(13) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 120.21(14) . . ?
C22 C20 C19 117.94(13) . . ?
C22 C20 C21 121.85(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22 119.5 . . ?
C20 C22 C23 121.06(13) . . ?
C23 C22 H22 119.5 . . ?
C17 C23 C22 120.87(13) . . ?
C17 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.106
_oxdiff_exptl_absorpt_empirical_full_min 0.925
####################################################################### 
# 
# 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_MM-XIV-8-F2(exp_402)
_database_code_depnum_ccdc_archive 'CCDC 1895672'
loop_
_audit_author_name
_audit_author_address
'Vickie McKee'
;Dublin City Univ and Univ Southern Denmark
Republic of Ireland
;
_audit_update_record             
;
2019-02-05 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H23O5
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                   6.80314(4)
_cell_length_b                   12.83574(7)
_cell_length_c                   22.67729(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1980.257(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34239
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      74.4570
_cell_measurement_theta_min      3.8850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 1 0.0273
1 0 1 0.1525
0 0 1 0.0718
0 0 -1 0.1102
1 0 -2 0.0957
-1 0 0 0.0784
0 8 -3 0.0285
-1 0 -1 0.0877
-1 7 -7 0.0394

_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -2.0000 1.0000 -0.0620 -0.2416 -0.0028
1.0000 0.0000 1.0000 0.1566 -0.0612 0.1662
0.0000 0.0000 1.0000 -0.0353 -0.0107 0.0571
-0.0000 -0.0000 -1.0000 0.0353 0.0107 -0.0571
1.0000 0.0000 -2.0000 0.2624 -0.0292 -0.0050
-1.0000 -0.0000 -0.0000 -0.1919 0.0505 -0.1091
-0.0000 8.0000 -2.9999 0.2129 0.9555 0.0684
-1.0000 -0.0000 -1.0000 -0.1566 0.0612 -0.1662
-0.6663 7.1371 -7.2718 0.2242 0.9353 -0.2740

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.643
_diffrn_reflns_theta_min         3.899
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  31.00   1.00    0.50    --   38.00  90.00  26.87   25
  2  ω      9.00  34.00   1.00    0.50    --   42.00  92.00 115.26   25
  3  ω     13.00  38.00   1.00    0.50    --   46.00  92.00-127.95   25
  4  ω     34.00  65.00   1.00    0.50    --   48.91  38.00  30.00   31
  5  ω    -92.00  -9.00   1.00    0.50    --  -49.16 125.00-180.00   83
  6  ω    -60.00 -28.00   1.00    0.50    --  -49.16 -57.00 -90.00   32
  7  ω   -104.00 -29.00   1.00    0.50    --  -49.16 -19.00  90.00   75
  8  ω    -49.00 -23.00   1.00    0.50    --  -49.16 -77.00  30.00   26
  9  ω    -75.00 -31.00   1.00    0.50    --  -49.16 -48.00 -13.59   44
 10  ω   -115.00 -62.00   1.00    0.50    --  -49.16 -57.00 -90.00   53
 11  ω   -110.00 -30.00   1.00    0.50    --  -49.16 -51.00 176.93   80
 12  ω    -98.00 -55.00   1.00    0.50    --  -49.16 -77.00  30.00   43
 13  ω     19.00  44.00   1.00    0.50    --   50.00  89.00  20.20   25
 14  ω     19.00  44.00   1.00    0.50    --   50.00  90.00 129.59   25
 15  ω     18.00  43.00   1.00    0.50    --   50.00  91.00 -84.76   25
 16  ω     29.00  55.00   1.00    0.50    --   58.00  82.00 -40.71   26
 17  ω     35.00  61.00   1.00    0.50    --   62.00  78.00 -10.83   26
 18  ω     33.00  60.00   1.00    0.50    --   62.00  82.00-148.42   27
 19  ω     95.00 122.00   1.00    0.50    --   62.00  82.00-148.42   27
 20  ω     37.00  63.00   1.00    0.50    --   66.00  82.00  14.81   26
 21  ω     40.00  67.00   1.00    0.50    --   66.00  76.00-118.93   27
 22  ω    -63.00 -37.00   1.00    0.77    --  -66.00 -82.00-104.36   26
 23  ω    110.00 135.00   1.00    0.50    --   66.00  76.00-118.93   25
 24  ω     38.00  95.00   1.00    0.50    --   66.00  79.00  76.48   57
 25  ω     39.00  64.00   1.00    0.50    --   66.00  79.00 151.78   25
 26  ω     40.00  67.00   1.00    0.50    --   66.00  76.00  48.07   27
 27  ω    110.00 140.00   1.00    0.50    --   70.00  83.00 161.96   30
 28  ω     42.00  67.00   1.00    0.50    --   70.00  83.00 161.96   25
 29  ω     46.00  72.00   1.00    0.50    --   74.00  81.00-105.98   26
 30  ω    -72.00 -46.00   1.00    0.77    --  -74.00 -81.00 -99.09   26
 31  ω    -76.00 -50.00   1.00    0.77    --  -78.00 -81.00-167.38   26
 32  ω    -91.00 -22.00   1.00    0.77    --  -82.50 125.00  60.00   69
 33  ω    -81.00 -55.00   1.00    0.77    --  -82.50 -77.00   0.00   26
 34  ω    -82.00 -56.00   1.00    0.77    --  -82.50 -75.00-146.03   26
 35  ω   -105.00 -56.00   1.00    0.77    --  -82.50 -76.00  81.77   49
 36  ω    -82.00 -56.00   1.00    0.77    --  -82.50 -75.00  23.13   26
 37  ω    -81.00 -55.00   1.00    0.77    --  -82.50 -78.00-107.87   26
 38  ω    -83.00 -56.00   1.00    0.77    --  -82.50 -79.00  -9.71   27
 39  ω    -79.00 -54.00   1.00    0.77    --  -82.50 -80.00  54.40   25
 40  ω    -84.00 -57.00   1.00    0.77    --  -82.50 -72.00 127.57   27
 41  ω    -83.00 -57.00   1.00    0.77    --  -82.50 -72.00  92.79   26
 42  ω    -87.00 -55.00   1.00    0.77    --  -82.50 -78.00 116.22   32
 43  ω    -81.00 -55.00   1.00    0.77    --  -82.50 -77.00 -30.00   26
 44  ω    -82.00 -56.00   1.00    0.77    --  -82.50 -76.00 -70.97   26
 45  ω    -85.00 -58.00   1.00    0.77    --  -82.50 -69.00 -57.18   27
 46  ω    -82.00 -56.00   1.00    0.77    --  -82.50 -76.00 157.48   26
 47  ω     37.00 118.00   1.00    0.77    --  100.40-125.00  60.00   81
 48  ω     81.00 125.00   1.00    0.77    --  100.40  77.00 120.00   44
 49  ω     74.00 147.00   1.00    0.77    --  100.40  77.00 -90.00   73
 50  ω     73.00 159.00   1.00    0.77    --  100.40  77.00-180.00   86
 51  ω     98.00 164.00   1.00    0.77    --  100.40 125.00 -90.00   66
 52  ω     30.00  97.00   1.00    0.77    --  100.40 -94.00 -60.00   67
 53  ω     37.00  62.00   1.00    0.77    --  100.40 -61.00 150.00   25
 54  ω     74.00 149.00   1.00    0.77    --  100.40  77.00  60.00   75
 55  ω     75.00 156.00   1.00    0.77    --  100.40  77.00   0.00   81
 56  ω     33.00  59.00   1.00    0.77    --  100.40 -61.00 -30.00   26
 57  ω     73.00 142.00   1.00    0.77    --  100.40  77.00-150.00   69
 58  ω     38.00  91.00   1.00    0.77    --  100.40 -94.00-120.00   53
 59  ω     79.00 156.00   1.00    0.77    --  100.40  61.00 -30.00   77
 60  ω     28.00 108.00   1.00    0.77    --  100.40 -94.00  90.00   80
 61  ω    131.00 159.00   1.00    0.77    --  100.40  77.00 120.00   28
 62  ω     75.00 142.00   1.00    0.77    --  100.40  77.00 150.00   67
 63  ω     36.00  61.00   1.00    0.77    --  100.40 -61.00  90.00   25
 64  ω     73.00 166.00   1.00    0.77    --  100.40  77.00  90.00   93
 65  ω     35.00  61.00   1.00    0.77    --  100.40 -61.00  30.00   26
 66  ω     77.00 151.00   1.00    0.77    --  100.40  77.00-120.00   74
 67  ω     75.00 167.00   1.00    0.77    --  100.40  77.00  30.00   92
 68  ω     36.00 117.00   1.00    0.77    --  100.40-125.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1918661000
_diffrn_orient_matrix_UB_12      0.0133801000
_diffrn_orient_matrix_UB_13      -0.0352748000
_diffrn_orient_matrix_UB_21      -0.0505418000
_diffrn_orient_matrix_UB_22      0.1154347000
_diffrn_orient_matrix_UB_23      -0.0106859000
_diffrn_orient_matrix_UB_31      0.1091302000
_diffrn_orient_matrix_UB_32      0.0299586000
_diffrn_orient_matrix_UB_33      0.0570777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3972
_reflns_number_total             4043
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015a)'
_computing_molecular_graphics    'Mercury (Macrae at al., 2008)'
_computing_publication_material  
'Olex2 (Dolomanov et al. 2009), PublCIF (Westrip, 2010)'

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.029
_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)+(0.0369P)²+0.3681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0640
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.85486(16) 0.49708(9) 0.26077(5) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.7045(2) 0.45478(11) 0.27496(6) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.71541(17) 0.38944(8) 0.13565(4) 0.0248(2) Uani 1 1 d . . . . .
C2 C 0.5541(2) 0.40853(11) 0.22992(6) 0.0154(3) Uani 1 1 d . . . . .
O3 O 0.74538(16) 0.26387(8) 0.20454(4) 0.0219(2) Uani 1 1 d . . . . .
C3 C 0.6762(2) 0.35373(11) 0.18320(6) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.8852(3) 0.20910(14) 0.16779(8) 0.0323(4) Uani 1 1 d . . . . .
H4A H 0.818081 0.181935 0.132775 0.048 Uiso 1 1 calc GR . . . .
H4B H 0.942533 0.151170 0.190072 0.048 Uiso 1 1 calc GR . . . .
H4C H 0.989630 0.257086 0.155626 0.048 Uiso 1 1 calc GR . . . .
O4 O 0.45360(18) 0.58744(8) 0.21375(5) 0.0267(3) Uani 1 1 d . . . . .
C10 C 0.2925(2) 0.23953(11) 0.38186(6) 0.0186(3) Uani 1 1 d . . . . .
H10 H 0.341655 0.197225 0.350817 0.022 Uiso 1 1 calc R . . . .
C11 C 0.1965(2) 0.19337(12) 0.42954(6) 0.0219(3) Uani 1 1 d . . . . .
H11 H 0.180262 0.119880 0.430632 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1245(2) 0.25391(13) 0.47535(6) 0.0228(3) Uani 1 1 d . . . . .
H12 H 0.058364 0.222279 0.507612 0.027 Uiso 1 1 calc R . . . .
C13 C 0.1499(2) 0.36124(13) 0.47362(6) 0.0220(3) Uani 1 1 d . . . . .
H13 H 0.102080 0.403194 0.505010 0.026 Uiso 1 1 calc R . . . .
C14 C 0.2452(2) 0.40750(11) 0.42606(6) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.261757 0.480978 0.425321 0.022 Uiso 1 1 calc R . . . .
C15 C 0.6371(2) 0.42966(10) 0.33789(6) 0.0150(3) Uani 1 1 d . . . . .
C16 C 0.7581(2) 0.33290(11) 0.35574(6) 0.0182(3) Uani 1 1 d . . . . .
H16A H 0.745215 0.279181 0.325278 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.709203 0.305757 0.393375 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.896726 0.352343 0.359909 0.027 Uiso 1 1 calc GR . . . .
C17 C 0.6664(2) 0.52145(10) 0.37916(6) 0.0157(3) Uani 1 1 d . . . . .
C18 C 0.6298(2) 0.62243(11) 0.35923(6) 0.0188(3) Uani 1 1 d . . . . .
H18 H 0.587521 0.633035 0.319763 0.023 Uiso 1 1 calc R . . . .
C19 C 0.6541(2) 0.70744(11) 0.39612(7) 0.0203(3) Uani 1 1 d . . . . .
H19 H 0.630302 0.775522 0.381329 0.024 Uiso 1 1 calc R . . . .
C20 C 0.7131(2) 0.69483(11) 0.45466(6) 0.0203(3) Uani 1 1 d . . . . .
C21 C 0.7399(3) 0.78854(12) 0.49397(8) 0.0293(4) Uani 1 1 d . . . . .
H21A H 0.848887 0.831061 0.479174 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.769187 0.765423 0.534202 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.618954 0.830035 0.494060 0.044 Uiso 1 1 calc GR . . . .
C22 C 0.7452(2) 0.59416(12) 0.47493(6) 0.0217(3) Uani 1 1 d . . . . .
H22 H 0.782436 0.583491 0.514852 0.026 Uiso 1 1 calc R . . . .
C23 C 0.7237(2) 0.50849(11) 0.43769(6) 0.0188(3) Uani 1 1 d . . . . .
H23 H 0.748493 0.440445 0.452404 0.023 Uiso 1 1 calc R . . . .
C5 C 0.4360(2) 0.49672(11) 0.20186(6) 0.0176(3) Uani 1 1 d . . . . .
O5 O 0.30332(16) 0.45851(8) 0.16464(5) 0.0243(2) Uani 1 1 d . . . . .
C6 C 0.1708(3) 0.53361(13) 0.13804(8) 0.0282(3) Uani 1 1 d . . . . .
H6A H 0.247138 0.585533 0.116136 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.094647 0.568394 0.168987 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.081183 0.497634 0.111025 0.042 Uiso 1 1 calc GR . . . .
C8 C 0.41578(19) 0.40151(10) 0.32803(6) 0.0144(3) Uani 1 1 d . . . . .
H8 H 0.344012 0.468456 0.321320 0.017 Uiso 1 1 calc R . . . .
C7 C 0.4163(2) 0.34219(11) 0.26891(6) 0.0156(3) Uani 1 1 d . . . . .
H7A H 0.282476 0.338548 0.251868 0.019 Uiso 1 1 calc R . . . .
H7B H 0.467987 0.270625 0.273841 0.019 Uiso 1 1 calc R . . . .
C9 C 0.3169(2) 0.34757(11) 0.37945(6) 0.0153(3) 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
O1 C1 1.2021(18) . ?
C1 C2 1.5630(19) . ?
C1 C15 1.5330(19) . ?
O2 C3 1.2016(18) . ?
C2 C3 1.5192(19) . ?
C2 C5 1.5269(19) . ?
C2 C7 1.5445(18) . ?
O3 C3 1.3365(17) . ?
O3 C4 1.4469(18) . ?
O4 C5 1.2012(18) . ?
C10 C11 1.395(2) . ?
C10 C9 1.3977(19) . ?
C11 C12 1.387(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.391(2) . ?
C14 C9 1.395(2) . ?
C15 C16 1.5440(19) . ?
C15 C17 1.5178(18) . ?
C15 C8 1.5647(18) . ?
C17 C18 1.3951(19) . ?
C17 C23 1.3934(19) . ?
C18 C19 1.385(2) . ?
C19 C20 1.396(2) . ?
C20 C21 1.508(2) . ?
C20 C22 1.389(2) . ?
C22 C23 1.394(2) . ?
C5 O5 1.3296(18) . ?
O5 C6 1.4512(18) . ?
C8 C7 1.5418(18) . ?
C8 C9 1.5140(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 123.63(13) . . ?
O1 C1 C15 126.76(13) . . ?
C15 C1 C2 109.44(11) . . ?
C3 C2 C1 105.87(11) . . ?
C3 C2 C5 109.90(11) . . ?
C3 C2 C7 118.42(11) . . ?
C5 C2 C1 109.59(11) . . ?
C5 C2 C7 109.16(11) . . ?
C7 C2 C1 103.45(10) . . ?
C3 O3 C4 116.24(12) . . ?
O2 C3 C2 124.79(13) . . ?
O2 C3 O3 125.18(14) . . ?
O3 C3 C2 109.85(11) . . ?
C11 C10 C9 120.48(13) . . ?
C12 C11 C10 120.52(14) . . ?
C11 C12 C13 119.39(13) . . ?
C12 C13 C14 120.21(14) . . ?
C13 C14 C9 120.98(13) . . ?
C1 C15 C16 104.71(11) . . ?
C1 C15 C8 101.73(11) . . ?
C16 C15 C8 111.39(11) . . ?
C17 C15 C1 111.81(11) . . ?
C17 C15 C16 113.12(11) . . ?
C17 C15 C8 113.19(11) . . ?
C18 C17 C15 119.87(12) . . ?
C23 C17 C15 122.11(12) . . ?
C23 C17 C18 117.99(13) . . ?
C19 C18 C17 121.01(13) . . ?
C18 C19 C20 121.15(13) . . ?
C19 C20 C21 120.28(14) . . ?
C22 C20 C19 117.89(13) . . ?
C22 C20 C21 121.84(14) . . ?
C20 C22 C23 121.13(13) . . ?
C17 C23 C22 120.81(13) . . ?
O4 C5 C2 124.94(14) . . ?
O4 C5 O5 124.59(14) . . ?
O5 C5 C2 110.37(11) . . ?
C5 O5 C6 116.14(12) . . ?
C7 C8 C15 103.66(11) . . ?
C9 C8 C15 115.05(11) . . ?
C9 C8 C7 116.42(11) . . ?
C8 C7 C2 103.11(10) . . ?
C10 C9 C8 122.45(12) . . ?
C14 C9 C10 118.42(12) . . ?
C14 C9 C8 119.13(12) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.186
_oxdiff_exptl_absorpt_empirical_full_min 0.837
