# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_fxm-1118-2
_database_code_depnum_ccdc_archive 'CCDC 1476945'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.8740(4)
_cell_length_b                   8.2225(2)
_cell_length_c                   11.5745(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.962(2)
_cell_angle_gamma                90
_cell_volume                     1603.79(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4591
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.5400
_cell_measurement_theta_min      5.2630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8300
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.250
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -45.0000 -108.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   45.0000   42.0000 86

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 11 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 13 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega  100.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 17 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 19 omega   81.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 20 omega   90.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 21 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 22 omega   91.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   47.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   81.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega  100.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 28 omega   88.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 29 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   43.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -108.0000 39

#__ type_ start__ end____ width___ exp.time_
 31 omega   92.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   71.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 34 omega  114.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0052628000
_diffrn_orient_matrix_UB_12      0.0936865000
_diffrn_orient_matrix_UB_13      -0.1145816000
_diffrn_orient_matrix_UB_21      0.0863404000
_diffrn_orient_matrix_UB_22      -0.0576365000
_diffrn_orient_matrix_UB_23      -0.0088783000
_diffrn_orient_matrix_UB_31      -0.0295882000
_diffrn_orient_matrix_UB_32      -0.1516655000
_diffrn_orient_matrix_UB_33      -0.0674929000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                2700
_reflns_number_total             2782
_reflns_odcompleteness_completeness 99.94
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.418
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.074
_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)+(0.1030P)²+0.0640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00B(H00B), C00I(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00F,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.32190(12) 0.3275(3) 0.05715(17) 0.0516(5) Uani 1 1 d . . . . .
O002 O 0.31489(16) 0.7284(3) 0.2844(2) 0.0653(6) Uani 1 1 d . . . . .
O003 O 0.36834(19) 0.0869(3) 0.1178(3) 0.0774(8) Uani 1 1 d . . . . .
O004 O 0.53474(15) 0.3177(4) 0.1417(3) 0.0834(8) Uani 1 1 d . . . . .
C005 C 0.36405(15) 0.2291(4) 0.1282(3) 0.0463(6) Uani 1 1 d . . . . .
C006 C 0.48044(16) 0.4031(4) 0.1670(3) 0.0519(7) Uani 1 1 d . . . . .
C007 C 0.36045(14) 0.4567(3) 0.2875(2) 0.0381(5) Uani 1 1 d . . . . .
H007 H 0.3053 0.4210 0.2921 0.046 Uiso 1 1 calc R . . . .
C008 C 0.36123(15) 0.3593(3) 0.5013(2) 0.0467(6) Uani 1 1 d . . . . .
C009 C 0.36295(16) 0.6321(3) 0.2526(2) 0.0435(6) Uani 1 1 d . . . . .
C00A C 0.40798(14) 0.3296(3) 0.2212(2) 0.0422(6) Uani 1 1 d . . . . .
C00B C 0.41023(14) 0.4072(3) 0.4018(2) 0.0412(6) Uani 1 1 d . . . . .
H00B H 0.4553 0.4786 0.4223 0.049 Uiso 1 1 calc R . . . .
C00C C 0.33957(16) 0.4418(4) 0.5945(2) 0.0516(7) Uani 1 1 d . . . . .
H00C H 0.3059 0.3847 0.6410 0.062 Uiso 1 1 calc R . . . .
C00D C 0.48166(18) 0.5789(4) 0.1448(3) 0.0554(7) Uani 1 1 d . . . . .
H00D H 0.5225 0.6201 0.1025 0.066 Uiso 1 1 calc R . . . .
C00E C 0.42785(19) 0.6833(4) 0.1816(2) 0.0542(7) Uani 1 1 d . . . . .
H00E H 0.4317 0.7924 0.1615 0.065 Uiso 1 1 calc R . . . .
C00F C 0.35929(15) 0.6053(4) 0.6362(2) 0.0470(6) Uani 1 1 d . . . . .
C00G C 0.3969(2) 0.9115(5) 0.7339(3) 0.0638(8) Uani 1 1 d . . . . .
H00G H 0.4101 1.0120 0.7662 0.077 Uiso 1 1 calc R . . . .
C00H C 0.40334(17) 0.7198(4) 0.5781(2) 0.0509(6) Uani 1 1 d . . . . .
H00H H 0.4200 0.6949 0.5048 0.061 Uiso 1 1 calc R . . . .
C00I C 0.43198(17) 0.2473(3) 0.3390(3) 0.0495(7) Uani 1 1 d . . . . .
H00I H 0.4879 0.2154 0.3486 0.059 Uiso 1 1 calc R . . . .
C00J C 0.33337(18) 0.6532(5) 0.7448(3) 0.0591(8) Uani 1 1 d . . . . .
H00J H 0.3031 0.5811 0.7860 0.071 Uiso 1 1 calc R . . . .
C00K C 0.4229(2) 0.8688(4) 0.6261(3) 0.0576(7) Uani 1 1 d . . . . .
H00K H 0.4537 0.9412 0.5861 0.069 Uiso 1 1 calc R . . . .
C00L C 0.2820(2) 0.2518(5) -0.0425(3) 0.0638(9) Uani 1 1 d . . . . .
H00A H 0.3203 0.2231 -0.0975 0.096 Uiso 1 1 calc GR . . . .
H00F H 0.2442 0.3264 -0.0775 0.096 Uiso 1 1 calc GR . . . .
H00L H 0.2551 0.1555 -0.0187 0.096 Uiso 1 1 calc GR . . . .
C00M C 0.3744(2) 0.1294(4) 0.3877(3) 0.0617(8) Uani 1 1 d . . . . .
H00M H 0.3653 0.0251 0.3590 0.074 Uiso 1 1 calc R . . . .
C00N C 0.3382(2) 0.1912(4) 0.4759(3) 0.0586(8) Uani 1 1 d . . . . .
H00N H 0.3018 0.1338 0.5177 0.070 Uiso 1 1 calc R . . . .
C00O C 0.3515(2) 0.8036(5) 0.7920(3) 0.0651(9) Uani 1 1 d . . . . .
H00O H 0.3328 0.8319 0.8635 0.078 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
O001 C005 1.333(4) . ?
O001 C00L 1.446(3) . ?
O002 C009 1.204(4) . ?
O003 C005 1.178(4) . ?
O004 C006 1.202(4) . ?
C005 C00A 1.519(3) . ?
C006 C00A 1.528(4) . ?
C006 C00D 1.469(5) . ?
C007 H007 0.9800 . ?
C007 C009 1.499(4) . ?
C007 C00A 1.545(3) . ?
C007 C00B 1.582(3) . ?
C008 C00B 1.505(4) . ?
C008 C00C 1.341(4) . ?
C008 C00N 1.461(4) . ?
C009 C00E 1.465(4) . ?
C00A C00I 1.556(4) . ?
C00B H00B 0.9800 . ?
C00B C00I 1.556(4) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.461(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.335(5) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.394(4) . ?
C00F C00J 1.407(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.389(5) . ?
C00G C00O 1.371(6) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.378(5) . ?
C00I H00I 0.9800 . ?
C00I C00M 1.503(5) . ?
C00J H00J 0.9300 . ?
C00J C00O 1.381(6) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00F 0.9600 . ?
C00L H00L 0.9600 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.318(6) . ?
C00N H00N 0.9300 . ?
C00O H00O 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
C005 O001 C00L 116.3(3) . . ?
O001 C005 C00A 109.4(2) . . ?
O003 C005 O001 124.9(3) . . ?
O003 C005 C00A 125.6(3) . . ?
O004 C006 C00A 120.4(3) . . ?
O004 C006 C00D 120.9(3) . . ?
C00D C006 C00A 118.7(3) . . ?
C009 C007 H007 110.0 . . ?
C009 C007 C00A 119.6(2) . . ?
C009 C007 C00B 116.8(2) . . ?
C00A C007 H007 110.0 . . ?
C00A C007 C00B 88.53(18) . . ?
C00B C007 H007 110.0 . . ?
C00C C008 C00B 131.8(3) . . ?
C00C C008 C00N 124.1(3) . . ?
C00N C008 C00B 104.1(3) . . ?
O002 C009 C007 121.5(3) . . ?
O002 C009 C00E 121.1(3) . . ?
C00E C009 C007 117.4(2) . . ?
C005 C00A C006 107.2(2) . . ?
C005 C00A C007 118.2(2) . . ?
C005 C00A C00I 118.7(2) . . ?
C006 C00A C007 112.5(2) . . ?
C006 C00A C00I 110.7(2) . . ?
C007 C00A C00I 88.72(19) . . ?
C007 C00B H00B 114.9 . . ?
C008 C00B C007 114.7(2) . . ?
C008 C00B H00B 114.9 . . ?
C008 C00B C00I 106.8(2) . . ?
C00I C00B C007 87.40(18) . . ?
C00I C00B H00B 114.9 . . ?
C008 C00C H00C 114.2 . . ?
C008 C00C C00F 131.6(2) . . ?
C00F C00C H00C 114.2 . . ?
C006 C00D H00D 117.9 . . ?
C00E C00D C006 124.1(3) . . ?
C00E C00D H00D 117.9 . . ?
C009 C00E H00E 118.8 . . ?
C00D C00E C009 122.3(3) . . ?
C00D C00E H00E 118.8 . . ?
C00H C00F C00C 125.5(3) . . ?
C00H C00F C00J 116.1(3) . . ?
C00J C00F C00C 118.4(3) . . ?
C00K C00G H00G 120.4 . . ?
C00O C00G H00G 120.4 . . ?
C00O C00G C00K 119.2(3) . . ?
C00F C00H H00H 119.1 . . ?
C00K C00H C00F 121.9(3) . . ?
C00K C00H H00H 119.1 . . ?
C00A C00I H00I 115.0 . . ?
C00B C00I C00A 89.13(18) . . ?
C00B C00I H00I 115.0 . . ?
C00M C00I C00A 117.7(2) . . ?
C00M C00I C00B 101.3(2) . . ?
C00M C00I H00I 115.0 . . ?
C00F C00J H00J 118.9 . . ?
C00O C00J C00F 122.1(3) . . ?
C00O C00J H00J 118.9 . . ?
C00G C00K H00K 119.8 . . ?
C00H C00K C00G 120.4(3) . . ?
C00H C00K H00K 119.8 . . ?
O001 C00L H00A 109.5 . . ?
O001 C00L H00F 109.5 . . ?
O001 C00L H00L 109.5 . . ?
H00A C00L H00F 109.5 . . ?
H00A C00L H00L 109.5 . . ?
H00F C00L H00L 109.5 . . ?
C00I C00M H00M 123.9 . . ?
C00N C00M C00I 112.1(3) . . ?
C00N C00M H00M 123.9 . . ?
C008 C00N H00N 123.5 . . ?
C00M C00N C008 113.1(3) . . ?
C00M C00N H00N 123.5 . . ?
C00G C00O C00J 120.2(3) . . ?
C00G C00O H00O 119.9 . . ?
C00J C00O H00O 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C005 C00A C006 -78.5(3) . . . . ?
O001 C005 C00A C007 49.9(3) . . . . ?
O001 C005 C00A C00I 155.2(2) . . . . ?
O002 C009 C00E C00D -179.6(3) . . . . ?
O003 C005 C00A C006 99.2(4) . . . . ?
O003 C005 C00A C007 -132.4(3) . . . . ?
O003 C005 C00A C00I -27.1(5) . . . . ?
O004 C006 C00A C005 -69.4(4) . . . . ?
O004 C006 C00A C007 158.9(3) . . . . ?
O004 C006 C00A C00I 61.4(4) . . . . ?
O004 C006 C00D C00E -172.5(3) . . . . ?
C005 C00A C00I C00B -140.8(2) . . . . ?
C005 C00A C00I C00M -38.4(4) . . . . ?
C006 C00A C00I C00B 94.7(2) . . . . ?
C006 C00A C00I C00M -163.0(3) . . . . ?
C006 C00D C00E C009 2.3(4) . . . . ?
C007 C009 C00E C00D 2.4(4) . . . . ?
C007 C00A C00I C00B -18.99(19) . . . . ?
C007 C00A C00I C00M 83.4(3) . . . . ?
C007 C00B C00I C00A 18.55(19) . . . . ?
C007 C00B C00I C00M -99.6(2) . . . . ?
C008 C00B C00I C00A 133.6(2) . . . . ?
C008 C00B C00I C00M 15.5(2) . . . . ?
C008 C00C C00F C00H 5.3(5) . . . . ?
C008 C00C C00F C00J -173.7(3) . . . . ?
C009 C007 C00A C005 -98.8(3) . . . . ?
C009 C007 C00A C006 27.0(3) . . . . ?
C009 C007 C00A C00I 139.0(2) . . . . ?
C009 C007 C00B C008 111.3(3) . . . . ?
C009 C007 C00B C00I -141.5(2) . . . . ?
C00A C006 C00D C00E 8.5(4) . . . . ?
C00A C007 C009 O002 164.1(2) . . . . ?
C00A C007 C009 C00E -18.0(3) . . . . ?
C00A C007 C00B C008 -126.0(2) . . . . ?
C00A C007 C00B C00I -18.7(2) . . . . ?
C00A C00I C00M C00N -106.0(3) . . . . ?
C00B C007 C009 O002 -91.2(3) . . . . ?
C00B C007 C009 C00E 86.7(3) . . . . ?
C00B C007 C00A C005 140.8(2) . . . . ?
C00B C007 C00A C006 -93.3(2) . . . . ?
C00B C007 C00A C00I 18.66(19) . . . . ?
C00B C008 C00C C00F -3.8(5) . . . . ?
C00B C008 C00N C00M 8.5(3) . . . . ?
C00B C00I C00M C00N -10.9(3) . . . . ?
C00C C008 C00B C007 -99.2(3) . . . . ?
C00C C008 C00B C00I 165.8(3) . . . . ?
C00C C008 C00N C00M -172.1(3) . . . . ?
C00C C00F C00H C00K -176.6(3) . . . . ?
C00C C00F C00J C00O 178.1(3) . . . . ?
C00D C006 C00A C005 109.5(3) . . . . ?
C00D C006 C00A C007 -22.1(3) . . . . ?
C00D C006 C00A C00I -119.6(3) . . . . ?
C00F C00H C00K C00G -1.9(5) . . . . ?
C00F C00J C00O C00G -0.8(5) . . . . ?
C00H C00F C00J C00O -1.0(4) . . . . ?
C00I C00M C00N C008 1.9(4) . . . . ?
C00J C00F C00H C00K 2.4(4) . . . . ?
C00K C00G C00O C00J 1.4(5) . . . . ?
C00L O001 C005 O003 -3.0(5) . . . . ?
C00L O001 C005 C00A 174.7(2) . . . . ?
C00N C008 C00B C007 80.1(3) . . . . ?
C00N C008 C00B C00I -14.8(3) . . . . ?
C00N C008 C00C C00F 177.0(3) . . . . ?
C00O C00G C00K C00H 0.0(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_fxm-zhf-iso-125k
_database_code_depnum_ccdc_archive 'CCDC 1476944'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_audit_creation_date             2016-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 O6'
_chemical_formula_sum            'C22 H18 O6'
_chemical_formula_weight         378.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.67071(16)
_cell_length_b                   13.2339(2)
_cell_length_c                   9.6030(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.936(3)
_cell_angle_gamma                90
_cell_volume                     897.77(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    125
_cell_measurement_theta_max      72.3830
_cell_measurement_theta_min      4.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8864
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         5.001
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      125
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 10 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 11 omega   88.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  136.0000   44.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 19 omega   90.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 20 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 23 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 24 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 26 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 27 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
 28 omega  -33.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0409383000
_diffrn_orient_matrix_UB_12      -0.1137128000
_diffrn_orient_matrix_UB_13      0.0288829000
_diffrn_orient_matrix_UB_21      -0.1933250000
_diffrn_orient_matrix_UB_22      -0.0248409000
_diffrn_orient_matrix_UB_23      -0.1260898000
_diffrn_orient_matrix_UB_31      0.0921264000
_diffrn_orient_matrix_UB_32      -0.0014679000
_diffrn_orient_matrix_UB_33      -0.1167359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3173
_reflns_number_total             3210
_reflns_odcompleteness_completeness 99.94
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.321
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.063
_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)+(0.0887P)²+0.0553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00N(H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00K), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00P(H00D,H00H,H00I)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.3775(3) 0.37667(14) 0.6771(2) 0.0217(4) Uani 1 1 d . . . . .
O002 O 0.5461(3) 0.41788(17) 0.9177(2) 0.0247(5) Uani 1 1 d . . . . .
O003 O 1.1041(3) 0.42185(16) 0.9037(2) 0.0248(5) Uani 1 1 d . . . . .
O004 O -0.0287(3) 0.66840(17) 0.4474(2) 0.0265(5) Uani 1 1 d . . . . .
O005 O 0.4915(3) 0.58998(18) 1.0180(2) 0.0289(5) Uani 1 1 d . . . . .
H005 H 0.5385 0.5322 1.0213 0.043 Uiso 1 1 calc GR . . . .
O006 O 0.9588(3) 0.29463(18) 0.9706(3) 0.0337(6) Uani 1 1 d . . . . .
C007 C 0.3416(4) 0.5413(2) 0.7552(3) 0.0177(6) Uani 1 1 d . . . . .
C008 C 0.2129(4) 0.5687(2) 0.6090(3) 0.0172(5) Uani 1 1 d . . . . .
C009 C 0.2742(4) 0.5414(2) 0.3613(3) 0.0193(6) Uani 1 1 d . . . . .
C00A C 1.0975(4) 0.3413(2) 0.9913(3) 0.0216(6) Uani 1 1 d . . . . .
C00B C 0.4336(3) 0.4410(2) 0.7917(3) 0.0185(6) Uani 1 1 d . . . . .
C00C C 0.6189(4) 0.4987(2) 0.5283(3) 0.0184(6) Uani 1 1 d . . . . .
C00D C 0.3695(4) 0.6103(2) 0.8740(3) 0.0220(6) Uani 1 1 d . . . . .
C00E C 0.8730(4) 0.3813(2) 0.6560(3) 0.0231(6) Uani 1 1 d . . . . .
H00E H 0.9361 0.3194 0.6567 0.028 Uiso 1 1 calc R . . . .
C00F C 0.4575(4) 0.5303(2) 0.3887(3) 0.0195(6) Uani 1 1 d . . . . .
H00F H 0.4904 0.5449 0.3052 0.023 Uiso 1 1 calc R . . . .
C00G C 0.1408(4) 0.5796(2) 0.2149(3) 0.0232(6) Uani 1 1 d . . . . .
H00G H 0.1731 0.5911 0.1303 0.028 Uiso 1 1 calc R . . . .
C00H C 0.9380(4) 0.4451(2) 0.7796(3) 0.0204(6) Uani 1 1 d . . . . .
C00I C 0.1074(4) 0.6560(2) 0.5907(3) 0.0223(6) Uani 1 1 d . . . . .
C00J C 0.1556(4) 0.5198(2) 0.4556(3) 0.0189(6) Uani 1 1 d . . . . .
H00J H 0.1355 0.4455 0.4618 0.023 Uiso 1 1 calc R . . . .
C00K C -0.0300(4) 0.5964(2) 0.2144(3) 0.0260(7) Uani 1 1 d . . . . .
H00K H -0.1357 0.6194 0.1292 0.031 Uiso 1 1 calc R . . . .
C00L C 0.4601(4) 0.2765(2) 0.7102(4) 0.0267(7) Uani 1 1 d . . . . .
H00A H 0.4177 0.2364 0.6171 0.040 Uiso 1 1 calc GR . . . .
H00B H 0.4199 0.2434 0.7842 0.040 Uiso 1 1 calc GR . . . .
H00C H 0.5984 0.2819 0.7519 0.040 Uiso 1 1 calc GR . . . .
C00M C 0.7145(4) 0.4090(2) 0.5312(3) 0.0224(6) Uani 1 1 d . . . . .
H00M H 0.6700 0.3657 0.4455 0.027 Uiso 1 1 calc R . . . .
C00N C -0.0339(4) 0.5743(2) 0.3656(3) 0.0245(6) Uani 1 1 d . . . . .
H00N H -0.1453 0.5316 0.3569 0.029 Uiso 1 1 calc R . . . .
C00O C 0.6906(4) 0.5627(2) 0.6536(3) 0.0185(5) Uani 1 1 d . . . . .
H00O H 0.6296 0.6253 0.6526 0.022 Uiso 1 1 calc R . . . .
C00P C 1.2884(4) 0.3224(2) 1.1132(4) 0.0284(7) Uani 1 1 d . . . . .
H00D H 1.3572 0.2732 1.0775 0.043 Uiso 1 1 calc GR . . . .
H00H H 1.2733 0.2958 1.2031 0.043 Uiso 1 1 calc GR . . . .
H00I H 1.3597 0.3859 1.1387 0.043 Uiso 1 1 calc GR . . . .
C00Q C 0.1350(4) 0.7236(2) 0.7077(4) 0.0259(6) Uani 1 1 d . . . . .
H00Q H 0.0635 0.7843 0.6912 0.031 Uiso 1 1 calc R . . . .
C00R C 0.8501(4) 0.5360(2) 0.7798(3) 0.0208(6) Uani 1 1 d . . . . .
H00R H 0.8978 0.5796 0.8649 0.025 Uiso 1 1 calc R . . . .
C00S C 0.2695(4) 0.7002(2) 0.8488(4) 0.0265(7) Uani 1 1 d . . . . .
H00S H 0.2937 0.7465 0.9299 0.032 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
O001 C00B 1.323(3) . ?
O001 C00L 1.450(3) . ?
O002 C00B 1.220(3) . ?
O003 C00A 1.371(4) . ?
O003 C00H 1.398(3) . ?
O004 C00I 1.376(3) . ?
O004 C00N 1.465(4) . ?
O005 H005 0.8400 . ?
O005 C00D 1.361(4) . ?
O006 C00A 1.178(4) . ?
C007 C008 1.414(4) . ?
C007 C00B 1.479(4) . ?
C007 C00D 1.411(4) . ?
C008 C00I 1.381(4) . ?
C008 C00J 1.509(4) . ?
C009 C00F 1.335(4) . ?
C009 C00G 1.469(4) . ?
C009 C00J 1.540(4) . ?
C00A C00P 1.497(4) . ?
C00C C00F 1.487(4) . ?
C00C C00M 1.391(4) . ?
C00C C00O 1.397(4) . ?
C00D C00S 1.385(4) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.382(4) . ?
C00E C00M 1.383(4) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00K 1.327(4) . ?
C00H C00R 1.379(4) . ?
C00I C00Q 1.387(4) . ?
C00J H00J 1.0000 . ?
C00J C00N 1.549(4) . ?
C00K H00K 0.9500 . ?
C00K C00N 1.493(4) . ?
C00L H00A 0.9800 . ?
C00L H00B 0.9800 . ?
C00L H00C 0.9800 . ?
C00M H00M 0.9500 . ?
C00N H00N 1.0000 . ?
C00O H00O 0.9500 . ?
C00O C00R 1.392(4) . ?
C00P H00D 0.9800 . ?
C00P H00H 0.9800 . ?
C00P H00I 0.9800 . ?
C00Q H00Q 0.9500 . ?
C00Q C00S 1.381(4) . ?
C00R H00R 0.9500 . ?
C00S H00S 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
C00B O001 C00L 115.7(2) . . ?
C00A O003 C00H 117.1(2) . . ?
C00I O004 C00N 106.6(2) . . ?
C00D O005 H005 109.5 . . ?
C008 C007 C00B 123.4(2) . . ?
C00D C007 C008 117.6(2) . . ?
C00D C007 C00B 118.8(2) . . ?
C007 C008 C00J 133.2(2) . . ?
C00I C008 C007 119.3(2) . . ?
C00I C008 C00J 107.6(2) . . ?
C00F C009 C00G 121.0(2) . . ?
C00F C009 C00J 133.0(3) . . ?
C00G C009 C00J 106.0(2) . . ?
O003 C00A C00P 110.5(2) . . ?
O006 C00A O003 123.4(3) . . ?
O006 C00A C00P 126.1(3) . . ?
O001 C00B C007 114.2(2) . . ?
O002 C00B O001 122.6(3) . . ?
O002 C00B C007 123.2(3) . . ?
C00M C00C C00F 120.4(2) . . ?
C00M C00C C00O 118.2(3) . . ?
C00O C00C C00F 121.1(2) . . ?
O005 C00D C007 121.4(3) . . ?
O005 C00D C00S 117.5(3) . . ?
C00S C00D C007 121.0(3) . . ?
C00H C00E H00E 120.5 . . ?
C00H C00E C00M 118.9(3) . . ?
C00M C00E H00E 120.5 . . ?
C009 C00F C00C 130.7(2) . . ?
C009 C00F H00F 114.6 . . ?
C00C C00F H00F 114.6 . . ?
C009 C00G H00G 123.8 . . ?
C00K C00G C009 112.3(3) . . ?
C00K C00G H00G 123.8 . . ?
C00E C00H O003 120.1(3) . . ?
C00R C00H O003 118.3(3) . . ?
C00R C00H C00E 121.4(3) . . ?
O004 C00I C008 113.9(2) . . ?
O004 C00I C00Q 123.4(3) . . ?
C008 C00I C00Q 122.7(3) . . ?
C008 C00J C009 118.7(2) . . ?
C008 C00J H00J 110.9 . . ?
C008 C00J C00N 101.4(2) . . ?
C009 C00J H00J 110.9 . . ?
C009 C00J C00N 103.1(2) . . ?
C00N C00J H00J 110.9 . . ?
C00G C00K H00K 124.5 . . ?
C00G C00K C00N 111.0(2) . . ?
C00N C00K H00K 124.5 . . ?
O001 C00L H00A 109.5 . . ?
O001 C00L H00B 109.5 . . ?
O001 C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
C00C C00M H00M 119.3 . . ?
C00E C00M C00C 121.5(3) . . ?
C00E C00M H00M 119.3 . . ?
O004 C00N C00J 105.9(2) . . ?
O004 C00N C00K 110.4(2) . . ?
O004 C00N H00N 111.7 . . ?
C00J C00N H00N 111.7 . . ?
C00K C00N C00J 105.3(2) . . ?
C00K C00N H00N 111.7 . . ?
C00C C00O H00O 119.5 . . ?
C00R C00O C00C 120.9(3) . . ?
C00R C00O H00O 119.5 . . ?
C00A C00P H00D 109.5 . . ?
C00A C00P H00H 109.5 . . ?
C00A C00P H00I 109.5 . . ?
H00D C00P H00H 109.5 . . ?
H00D C00P H00I 109.5 . . ?
H00H C00P H00I 109.5 . . ?
C00I C00Q H00Q 121.0 . . ?
C00S C00Q C00I 118.0(3) . . ?
C00S C00Q H00Q 121.0 . . ?
C00H C00R C00O 119.0(3) . . ?
C00H C00R H00R 120.5 . . ?
C00O C00R H00R 120.5 . . ?
C00D C00S H00S 119.5 . . ?
C00Q C00S C00D 121.0(3) . . ?
C00Q C00S H00S 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O003 C00H C00R C00O 176.5(2) . . . . ?
O004 C00I C00Q C00S 176.6(2) . . . . ?
O005 C00D C00S C00Q -176.2(2) . . . . ?
C007 C008 C00I O004 -172.5(2) . . . . ?
C007 C008 C00I C00Q 6.4(4) . . . . ?
C007 C008 C00J C009 -86.4(4) . . . . ?
C007 C008 C00J C00N 161.7(3) . . . . ?
C007 C00D C00S C00Q 2.0(4) . . . . ?
C008 C007 C00B O001 -3.4(3) . . . . ?
C008 C007 C00B O002 179.3(2) . . . . ?
C008 C007 C00D O005 -179.7(2) . . . . ?
C008 C007 C00D C00S 2.1(4) . . . . ?
C008 C00I C00Q C00S -2.2(4) . . . . ?
C008 C00J C00N O004 21.2(3) . . . . ?
C008 C00J C00N C00K 138.2(2) . . . . ?
C009 C00G C00K C00N 1.8(4) . . . . ?
C009 C00J C00N O004 -102.1(2) . . . . ?
C009 C00J C00N C00K 14.8(3) . . . . ?
C00A O003 C00H C00E -70.0(3) . . . . ?
C00A O003 C00H C00R 114.6(3) . . . . ?
C00B C007 C008 C00I 168.0(2) . . . . ?
C00B C007 C008 C00J -10.2(4) . . . . ?
C00B C007 C00D O005 5.8(3) . . . . ?
C00B C007 C00D C00S -172.3(2) . . . . ?
C00C C00O C00R C00H 0.3(4) . . . . ?
C00D C007 C008 C00I -6.2(3) . . . . ?
C00D C007 C008 C00J 175.6(3) . . . . ?
C00D C007 C00B O001 170.7(2) . . . . ?
C00D C007 C00B O002 -6.6(4) . . . . ?
C00E C00H C00R C00O 1.2(4) . . . . ?
C00F C009 C00G C00K -172.9(3) . . . . ?
C00F C009 C00J C008 56.3(4) . . . . ?
C00F C009 C00J C00N 167.3(3) . . . . ?
C00F C00C C00M C00E 175.5(2) . . . . ?
C00F C00C C00O C00R -175.3(2) . . . . ?
C00G C009 C00F C00C 176.4(3) . . . . ?
C00G C009 C00J C008 -124.9(3) . . . . ?
C00G C009 C00J C00N -13.9(3) . . . . ?
C00G C00K C00N O004 102.9(3) . . . . ?
C00G C00K C00N C00J -10.9(3) . . . . ?
C00H O003 C00A O006 -3.3(4) . . . . ?
C00H O003 C00A C00P 176.6(2) . . . . ?
C00H C00E C00M C00C -0.6(4) . . . . ?
C00I O004 C00N C00J -18.6(3) . . . . ?
C00I O004 C00N C00K -132.1(2) . . . . ?
C00I C008 C00J C009 95.2(3) . . . . ?
C00I C008 C00J C00N -16.7(3) . . . . ?
C00I C00Q C00S C00D -2.0(4) . . . . ?
C00J C008 C00I O004 6.2(3) . . . . ?
C00J C008 C00I C00Q -174.9(2) . . . . ?
C00J C009 C00F C00C -5.0(5) . . . . ?
C00J C009 C00G C00K 8.2(3) . . . . ?
C00L O001 C00B O002 -0.7(3) . . . . ?
C00L O001 C00B C007 -178.0(2) . . . . ?
C00M C00C C00F C009 114.9(3) . . . . ?
C00M C00C C00O C00R -1.9(4) . . . . ?
C00M C00E C00H O003 -176.3(2) . . . . ?
C00M C00E C00H C00R -1.1(4) . . . . ?
C00N O004 C00I C008 8.2(3) . . . . ?
C00N O004 C00I C00Q -170.7(3) . . . . ?
C00O C00C C00F C009 -71.8(4) . . . . ?
C00O C00C C00M C00E 2.0(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-28
_olex2_submission_special_instructions 'No special instructions were received'
