# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_I
_audit_block_doi                 10.5517/ccv73cj
_database_code_depnum_ccdc_archive 'CCDC 781397'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S1600536810018027 2010
_audit_update_record             
;
2010-06-17 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Bis(4-chlorophenyl)-2-hydroxybutane-1,4-dione
;

_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 Cl2 O3'
_chemical_formula_sum            'C16 H12 Cl2 O3'
_chemical_formula_iupac          'C16 H12 Cl2 O3'
_chemical_formula_weight         323.16
_chemical_melting_point          ?
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
loop_
_symmetry_equiv_pos_as_xyz

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


_cell_length_a                   34.800(8)

_cell_length_b                   7.4221(14)

_cell_length_c                   5.6535(13)

_cell_angle_alpha                90.00

_cell_angle_beta                 95.925(2)

_cell_angle_gamma                90.00

_cell_volume                     1452.4(5)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    1044

_cell_measurement_theta_min      2.35

_cell_measurement_theta_max      24.43

_cell_measurement_temperature    273(2)

_exptl_crystal_description       column

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.12

_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.08

_exptl_crystal_density_diffrn    1.478

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    0.453

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_absorpt_correction_T_min  0.947

_exptl_absorpt_correction_T_max  0.964

_exptl_special_details           
;

;


_diffrn_ambient_temperature      273(2)

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            3531

_diffrn_reflns_av_R_equivalents  0.0252

_diffrn_reflns_av_sigmaI/netI    0.0287

_diffrn_reflns_theta_min         2.35

_diffrn_reflns_theta_max         24.95

_diffrn_reflns_theta_full        24.95

_diffrn_measured_fraction_theta_max 0.989

_diffrn_measured_fraction_theta_full 0.989

_diffrn_reflns_limit_h_min       -38

_diffrn_reflns_limit_h_max       40

_diffrn_reflns_limit_k_min       -7

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -6

_diffrn_reflns_limit_l_max       6

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_reflns_number_total             1256

_reflns_number_gt                998

_reflns_threshold_expression     I>2sigma(I)

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_R_factor_all          0.0714

_refine_ls_R_factor_gt           0.0568

_refine_ls_wR_factor_gt          0.1524

_refine_ls_wR_factor_ref         0.1629

_refine_ls_goodness_of_fit_ref   1.054

_refine_ls_restrained_S_all      1.053

_refine_ls_number_reflns         1256

_refine_ls_number_parameters     190

_refine_ls_number_restraints     9

_refine_ls_hydrogen_treatment    constr

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1063P)²+0.4654P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.396

_refine_diff_density_min         -0.213

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details nd

_refine_ls_abs_structure_Flack   ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source

C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_computing_data_collection       'SMART (Bruker, 2001)'

_computing_cell_refinement       'SAINT (Bruker, 2001)'

_computing_data_reduction        'SAINT (Bruker, 2001)'

_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group

C C1 1.04214(18) 0.1713(8) 0.3400(11) 0.0369(15) Uani d . 1 1 . .
H H1 1.0356 0.1204 0.4809 0.044 Uiso calc R 1 1 . .
C C2 1.0810(2) 0.1845(10) 0.2991(14) 0.053(2) Uani d . 1 1 . .
H H2 1.1002 0.1385 0.4089 0.063 Uiso calc R 1 1 . .
C C3 1.0905(2) 0.2672(9) 0.0921(14) 0.049(2) Uani d . 1 1 . .
C C4 1.0605(2) 0.3249(10) -0.0726(13) 0.049(2) Uani d . 1 1 . .
H H4 1.0664 0.3745 -0.2154 0.058 Uiso calc R 1 1 . .
C C5 1.0234(2) 0.3116(8) -0.0327(12) 0.0403(16) Uani d . 1 1 . .
H H5 1.0043 0.3556 -0.1448 0.048 Uiso calc R 1 1 . .
C C6 1.0133(2) 0.2332(8) 0.1732(12) 0.0357(16) Uani d . 1 1 . .
C C7 0.9724(2) 0.2035(8) 0.2253(12) 0.0374(16) Uani d . 1 1 . .
C C8 0.9403(2) 0.2685(8) 0.0412(13) 0.0383(14) Uani d U 1 1 . .
H H8 0.9443 0.2140 -0.1121 0.046 Uiso calc R 1 1 . .
C C9 0.9007(2) 0.2137(9) 0.1027(12) 0.0412(15) Uani d U 1 1 . .
H H9A 0.8999 0.0839 0.1210 0.049 Uiso calc R 1 1 . .
H H9B 0.8961 0.2678 0.2533 0.049 Uiso calc R 1 1 . .
C C10 0.8693(2) 0.2712(9) -0.0860(13) 0.0454(18) Uani d . 1 1 . .
C C11 0.8287(2) 0.2621(8) -0.0279(12) 0.0362(16) Uani d . 1 1 . .
C C12 0.8185(2) 0.1854(9) 0.1838(11) 0.0444(18) Uani d . 1 1 . .
H H12 0.8377 0.1432 0.2964 0.053 Uiso calc R 1 1 . .
C C13 0.7794(2) 0.1712(10) 0.2287(12) 0.0465(19) Uani d . 1 1 . .
H H13 0.7725 0.1146 0.3649 0.056 Uiso calc R 1 1 . .
C C14 0.7524(2) 0.2427(10) 0.0672(14) 0.053(2) Uani d . 1 1 . .
C C15 0.7606(2) 0.3157(9) -0.1456(15) 0.0489(18) Uani d . 1 1 . .
H H15 0.7409 0.3558 -0.2564 0.059 Uiso calc R 1 1 . .
C C16 0.7982(2) 0.3280(9) -0.1908(12) 0.0473(18) Uani d . 1 1 . .
H H16 0.8040 0.3809 -0.3319 0.057 Uiso calc R 1 1 . .
Cl Cl1 1.13745(6) 0.2822(4) 0.0298(3) 0.0922(9) Uani d . 1 1 . .
Cl Cl2 0.70386(6) 0.2245(4) 0.1208(4) 0.0948(10) Uani d . 1 1 . .
O O1 0.96490(15) 0.1328(6) 0.4095(9) 0.0515(12) Uani d . 1 1 . .
O O2 0.94303(14) 0.4587(5) 0.0178(8) 0.0501(10) Uani d . 1 1 . .
H H2A 0.9434 0.5058 0.1492 0.075 Uiso calc R 1 1 . .
O O3 0.87583(16) 0.3179(10) -0.2824(10) 0.084(2) Uani d . 1 1 . .



_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

C1 C6 . 1.384(10) ?
C1 C2 . 1.398(10) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.391(12) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.393(11) ?
C3 Cl1 . 1.711(8) ?
C4 C5 . 1.334(9) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(9) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.499(10) ?
C7 O1 . 1.218(8) ?
C7 C8 . 1.525(10) ?
C8 O2 . 1.422(7) ?
C8 C9 . 1.509(7) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.507(11) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O3 . 1.206(9) ?
C10 C11 . 1.485(10) ?
C11 C12 . 1.404(9) ?
C11 C16 . 1.419(10) ?
C12 C13 . 1.413(9) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.349(11) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.376(12) ?
C14 Cl2 . 1.753(8) ?
C15 C16 . 1.361(10) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
O2 H2A . 0.8200 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

C6 C1 C2 . . 120.7(6) ?
C6 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
C3 C2 C1 . . 119.2(7) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 118.1(8) ?
C2 C3 Cl1 . . 121.1(6) ?
C4 C3 Cl1 . . 120.6(6) ?
C5 C4 C3 . . 122.3(7) ?
C5 C4 H4 . . 118.8 ?
C3 C4 H4 . . 118.8 ?
C4 C5 C6 . . 120.7(7) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.9(7) ?
C5 C6 C7 . . 124.0(6) ?
C1 C6 C7 . . 117.1(6) ?
O1 C7 C6 . . 121.4(6) ?
O1 C7 C8 . . 120.9(7) ?
C6 C7 C8 . . 117.6(6) ?
O2 C8 C9 . . 111.2(5) ?
O2 C8 C7 . . 109.0(5) ?
C9 C8 C7 . . 112.3(5) ?
O2 C8 H8 . . 108.1 ?
C9 C8 H8 . . 108.1 ?
C7 C8 H8 . . 108.1 ?
C10 C9 C8 . . 111.8(5) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
O3 C10 C11 . . 119.3(6) ?
O3 C10 C9 . . 122.8(6) ?
C11 C10 C9 . . 117.8(6) ?
C12 C11 C16 . . 117.0(7) ?
C12 C11 C10 . . 122.6(6) ?
C16 C11 C10 . . 120.4(6) ?
C11 C12 C13 . . 121.2(6) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C14 C13 C12 . . 117.7(6) ?
C14 C13 H13 . . 121.2 ?
C12 C13 H13 . . 121.2 ?
C13 C14 C15 . . 123.6(7) ?
C13 C14 Cl2 . . 117.9(6) ?
C15 C14 Cl2 . . 118.2(6) ?
C16 C15 C14 . . 118.8(7) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C15 C16 C11 . . 121.6(7) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
C8 O2 H2A . . 109.5 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA

O2 H2A O2 2_565 0.82 2.10 2.894(6) 163
C1 H1 Cg1 2_555 0.93 2.89 3.507(6) 125
C4 H4 Cg1 2_564 0.93 2.97 3.600(6) 126
C13 H13 Cg2 2_555 0.93 2.88 3.517(6) 127
C16 H16 Cg2 2_564 0.93 2.90 3.544(6) 128
####################################################################### 
# 
# 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_wyh_0125
_database_code_depnum_ccdc_archive 'CCDC 1435061'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_audit_creation_date             2015-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H24 O3'
_chemical_formula_sum            'C27 H24 O3'
_chemical_formula_weight         396.46
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.4749(5)
_cell_length_b                   10.5376(4)
_cell_length_c                   17.8795(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.301(4)
_cell_angle_gamma                90.00
_cell_volume                     2127.10(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1956
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.2700
_cell_measurement_theta_min      3.9730
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8532
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.61
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00   25.20   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   92.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   85.00   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   57.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00  -24.80   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000 -150.0000 21
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0622822000
_diffrn_orient_matrix_UB_12      -0.0077078000
_diffrn_orient_matrix_UB_13      -0.0045533000
_diffrn_orient_matrix_UB_21      -0.0030616000
_diffrn_orient_matrix_UB_22      -0.0097753000
_diffrn_orient_matrix_UB_23      -0.0395426000
_diffrn_orient_matrix_UB_31      0.0077105000
_diffrn_orient_matrix_UB_32      -0.0661648000
_diffrn_orient_matrix_UB_33      0.0063738000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2961
_reflns_number_total             4170
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.8297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C9(H9), C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C19(H19a,H19b,H19c), C28(H28a,H28b,H28c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.43677(14) 0.61088(15) 0.04497(10) 0.0490(5) Uani 1 d . . .
O2 O 0.78476(13) 0.39799(13) 0.18261(10) 0.0408(4) Uani 1 d . . .
O3 O 0.45116(14) 0.68392(14) 0.22120(10) 0.0440(4) Uani 1 d . . .
C1 C 0.22831(19) 0.4629(2) 0.03004(13) 0.0359(5) Uani 1 d . . .
H1 H 0.2324 0.5215 -0.0083 0.043 Uiso 1 calc . . R
C2 C 0.12578(19) 0.3938(2) 0.02936(14) 0.0387(6) Uani 1 d . . .
H2 H 0.0625 0.4047 -0.0106 0.046 Uiso 1 calc . . R
C3 C 0.11522(19) 0.3089(2) 0.08670(14) 0.0379(6) Uani 1 d . . .
C4 C 0.21186(19) 0.2921(2) 0.14507(13) 0.0370(5) Uani 1 d . . .
H4 H 0.2062 0.2359 0.1844 0.044 Uiso 1 calc . . R
C5 C 0.31647(19) 0.35816(19) 0.14537(12) 0.0330(5) Uani 1 d . . .
H5 H 0.3809 0.3444 0.1842 0.040 Uiso 1 calc . . R
C6 C 0.32575(18) 0.44490(19) 0.08808(12) 0.0303(5) Uani 1 d . . .
C7 C 0.0025(2) 0.2346(3) 0.08564(17) 0.0547(7) Uani 1 d . . .
H7A H -0.0645 0.2889 0.0696 0.082 Uiso 1 calc . . GR
H7B H 0.0004 0.2030 0.1357 0.082 Uiso 1 calc . . GR
H7C H -0.0001 0.1647 0.0509 0.082 Uiso 1 calc . . GR
C8 C 0.43587(19) 0.5200(2) 0.08698(13) 0.0334(5) Uani 1 d . . .
C9 C 0.54627(17) 0.4740(2) 0.13754(12) 0.0317(5) Uani 1 d . . .
H9 H 0.5727 0.3899 0.1242 0.038 Uiso 1 calc . . R
C10 C 0.57070(17) 0.50224(19) 0.22239(12) 0.0301(5) Uani 1 d . . .
H10 H 0.6089 0.4348 0.2558 0.036 Uiso 1 calc . . R
C11 C 0.64466(17) 0.5629(2) 0.16826(12) 0.0316(5) Uani 1 d . . .
H11 H 0.6325 0.6533 0.1568 0.038 Uiso 1 calc . . R
C12 C 0.76800(18) 0.5121(2) 0.17549(12) 0.0306(5) Uani 1 d . . .
C13 C 0.86899(17) 0.59983(19) 0.17278(12) 0.0280(5) Uani 1 d . . .
C14 C 0.85528(19) 0.7285(2) 0.15553(12) 0.0343(5) Uani 1 d . . .
H14 H 0.7807 0.7658 0.1497 0.041 Uiso 1 calc . . R
C15 C 0.95296(19) 0.8008(2) 0.14714(13) 0.0379(5) Uani 1 d . . .
H15 H 0.9430 0.8866 0.1357 0.046 Uiso 1 calc . . R
C16 C 1.06504(19) 0.7482(2) 0.15538(12) 0.0368(5) Uani 1 d . . .
C17 C 1.07896(19) 0.6215(2) 0.17637(13) 0.0386(6) Uani 1 d . . .
H17 H 1.1542 0.5857 0.1849 0.046 Uiso 1 calc . . R
C18 C 0.98277(18) 0.5482(2) 0.18476(12) 0.0340(5) Uani 1 d . . .
H18 H 0.9938 0.4633 0.1985 0.041 Uiso 1 calc . . R
C19 C 1.1698(2) 0.8244(3) 0.14033(15) 0.0525(7) Uani 1 d . . .
H19A H 1.2396 0.7983 0.1748 0.079 Uiso 1 calc . . GR
H19B H 1.1556 0.9129 0.1476 0.079 Uiso 1 calc . . GR
H19C H 1.1807 0.8104 0.0890 0.079 Uiso 1 calc . . GR
C20 C 0.48439(17) 0.58458(19) 0.25320(13) 0.0308(5) Uani 1 d . . .
C22 C 0.43697(17) 0.54215(18) 0.32075(12) 0.0272(5) Uani 1 d . . .
C23 C 0.34886(19) 0.61522(19) 0.34467(13) 0.0343(5) Uani 1 d . . .
H23 H 0.3223 0.6889 0.3184 0.041 Uiso 1 calc . . R
C24 C 0.3010(2) 0.5793(2) 0.40670(14) 0.0393(6) Uani 1 d . . .
H24 H 0.2429 0.6297 0.4220 0.047 Uiso 1 calc . . R
C25 C 0.33758(19) 0.4694(2) 0.44690(13) 0.0351(5) Uani 1 d . . .
C26 C 0.42596(19) 0.39714(19) 0.42384(13) 0.0337(5) Uani 1 d . . .
H26 H 0.4527 0.3240 0.4506 0.040 Uiso 1 calc . . R
C27 C 0.47482(18) 0.43229(18) 0.36160(12) 0.0299(5) Uani 1 d . . .
H27 H 0.5335 0.3822 0.3468 0.036 Uiso 1 calc . . R
C28 C 0.2831(2) 0.4272(2) 0.51320(14) 0.0495(6) Uani 1 d . . .
H28A H 0.2926 0.3372 0.5197 0.074 Uiso 1 calc . . GR
H28B H 0.2003 0.4480 0.5038 0.074 Uiso 1 calc . . GR
H28C H 0.3215 0.4697 0.5585 0.074 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.219(2) . ?
O2 C12 1.220(2) . ?
O3 C20 1.221(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 C4 1.392(3) . ?
C3 C7 1.509(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(3) . ?
C6 C8 1.494(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.499(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.522(3) . ?
C9 C11 1.494(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.536(3) . ?
C10 C20 1.494(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.497(3) . ?
C12 C13 1.490(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.395(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 C17 1.389(3) . ?
C16 C19 1.509(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C22 1.480(3) . ?
C22 C23 1.397(3) . ?
C22 C27 1.396(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(3) . ?
C25 C26 1.388(3) . ?
C25 C28 1.503(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(3) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.5(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 C7 121.0(2) . . ?
C4 C3 C7 120.6(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C8 119.04(19) . . ?
C5 C6 C1 118.69(19) . . ?
C5 C6 C8 122.27(19) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C6 121.65(19) . . ?
O1 C8 C9 121.76(19) . . ?
C6 C8 C9 116.53(18) . . ?
C8 C9 H9 114.2 . . ?
C8 C9 C10 121.55(18) . . ?
C10 C9 H9 114.2 . . ?
C11 C9 C8 121.40(18) . . ?
C11 C9 H9 114.2 . . ?
C11 C9 C10 61.23(14) . . ?
C9 C10 H10 116.7 . . ?
C9 C10 C11 58.48(13) . . ?
C11 C10 H10 116.7 . . ?
C20 C10 C9 117.70(18) . . ?
C20 C10 H10 116.7 . . ?
C20 C10 C11 117.92(17) . . ?
C9 C11 C10 60.30(13) . . ?
C9 C11 H11 117.6 . . ?
C9 C11 C12 116.64(18) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 C10 114.66(17) . . ?
C12 C11 H11 117.6 . . ?
O2 C12 C11 119.35(18) . . ?
O2 C12 C13 120.39(18) . . ?
C13 C12 C11 120.26(17) . . ?
C14 C13 C12 123.62(18) . . ?
C14 C13 C18 118.63(18) . . ?
C18 C13 C12 117.68(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 118.25(19) . . ?
C15 C16 C19 121.5(2) . . ?
C17 C16 C19 120.2(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C10 119.8(2) . . ?
O3 C20 C22 120.79(19) . . ?
C22 C20 C10 119.35(18) . . ?
C23 C22 C20 118.37(18) . . ?
C27 C22 C20 123.52(18) . . ?
C27 C22 C23 118.11(19) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.3(2) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 C28 121.7(2) . . ?
C26 C25 C28 120.1(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.67(19) . . ?
C26 C27 H27 119.7 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
O1 C8 C9 C10 103.2(3) . . . . ?
O1 C8 C9 C11 29.8(3) . . . . ?
O2 C12 C13 C14 171.8(2) . . . . ?
O2 C12 C13 C18 -5.1(3) . . . . ?
O3 C20 C22 C23 3.2(3) . . . . ?
O3 C20 C22 C27 -177.3(2) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 C7 179.6(2) . . . . ?
C1 C6 C8 O1 12.8(3) . . . . ?
C1 C6 C8 C9 -164.48(19) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C8 179.41(19) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C8 178.79(19) . . . . ?
C5 C6 C8 O1 -166.7(2) . . . . ?
C5 C6 C8 C9 16.0(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C6 C8 C9 C10 -79.6(2) . . . . ?
C6 C8 C9 C11 -152.90(19) . . . . ?
C7 C3 C4 C5 178.6(2) . . . . ?
C8 C9 C10 C11 -111.1(2) . . . . ?
C8 C9 C10 C20 -3.8(3) . . . . ?
C8 C9 C11 C10 111.4(2) . . . . ?
C8 C9 C11 C12 -144.1(2) . . . . ?
C9 C10 C11 C12 -107.8(2) . . . . ?
C9 C10 C20 O3 -47.7(3) . . . . ?
C9 C10 C20 C22 130.1(2) . . . . ?
C9 C11 C12 O2 -25.3(3) . . . . ?
C9 C11 C12 C13 153.71(19) . . . . ?
C10 C9 C11 C12 104.5(2) . . . . ?
C10 C11 C12 O2 42.4(3) . . . . ?
C10 C11 C12 C13 -138.61(19) . . . . ?
C10 C20 C22 C23 -174.60(18) . . . . ?
C10 C20 C22 C27 4.8(3) . . . . ?
C11 C9 C10 C20 107.4(2) . . . . ?
C11 C10 C20 O3 19.3(3) . . . . ?
C11 C10 C20 C22 -162.82(18) . . . . ?
C11 C12 C13 C14 -7.2(3) . . . . ?
C11 C12 C13 C18 175.93(19) . . . . ?
C12 C13 C14 C15 -173.9(2) . . . . ?
C12 C13 C18 C17 174.2(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C13 C18 C17 -2.9(3) . . . . ?
C14 C15 C16 C17 -3.3(3) . . . . ?
C14 C15 C16 C19 175.2(2) . . . . ?
C15 C16 C17 C18 3.5(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C18 C13 C14 C15 3.0(3) . . . . ?
C19 C16 C17 C18 -175.1(2) . . . . ?
C20 C10 C11 C9 -107.0(2) . . . . ?
C20 C10 C11 C12 145.19(19) . . . . ?
C20 C22 C23 C24 179.4(2) . . . . ?
C20 C22 C27 C26 -179.31(19) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C22 C27 C26 0.1(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C23 C24 C25 C28 -178.0(2) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C25 C26 C27 C22 0.5(3) . . . . ?
C27 C22 C23 C24 -0.1(3) . . . . ?
C28 C25 C26 C27 178.1(2) . . . . ?

_olex2_date_sample_data_collection 2015-01-27
_olex2_submission_special_instructions 'No special instructions were received'
