# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_is_mm62
_database_code_depnum_ccdc_archive 'CCDC 1405371'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
3,3'-carbonylbis(4H-chromen-4-one)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H10 O5'
_chemical_formula_sum            'C19 H10 O5'
_chemical_formula_weight         318.27

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   16.6528(7)
_cell_length_b                   6.6881(3)
_cell_length_c                   13.5348(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.809(2)
_cell_angle_gamma                90.00
_cell_volume                     1379.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6992
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      30.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15596
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         29.99
_reflns_number_total             4026
_reflns_number_gt                3478
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0514P)²+0.5179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23113(6) -0.05953(14) 0.14397(7) 0.0309(2) Uani 1 1 d . . .
O2 O 0.47249(5) -0.15126(12) 0.13817(7) 0.02423(18) Uani 1 1 d . . .
O3 O 0.37193(6) 0.41650(12) 0.09854(8) 0.0286(2) Uani 1 1 d . . .
O4 O 0.11738(6) 0.51032(14) 0.08833(7) 0.0292(2) Uani 1 1 d . . .
O5 O 0.22341(6) 0.25510(14) -0.10697(7) 0.0298(2) Uani 1 1 d . . .
C1 C 0.26057(7) 0.07435(17) 0.10682(9) 0.0220(2) Uani 1 1 d . . .
C2 C 0.35159(7) 0.06651(16) 0.11233(8) 0.0201(2) Uani 1 1 d . . .
C3 C 0.39018(7) -0.11635(17) 0.12779(9) 0.0223(2) Uani 1 1 d . . .
H3 H 0.3563 -0.2280 0.1315 0.027 Uiso 1 1 calc R . .
C4 C 0.52353(7) 0.00944(16) 0.13430(8) 0.0207(2) Uani 1 1 d . . .
C5 C 0.60851(8) -0.03504(18) 0.14492(9) 0.0254(2) Uani 1 1 d . . .
H5 H 0.6295 -0.1688 0.1556 0.031 Uiso 1 1 calc R . .
C6 C 0.66139(8) 0.1197(2) 0.13959(9) 0.0272(2) Uani 1 1 d . . .
H6 H 0.7194 0.0919 0.1466 0.033 Uiso 1 1 calc R . .
C7 C 0.63069(8) 0.31762(19) 0.12389(9) 0.0263(2) Uani 1 1 d . . .
H7 H 0.6675 0.4228 0.1197 0.032 Uiso 1 1 calc R . .
C8 C 0.54655(7) 0.35855(17) 0.11461(9) 0.0229(2) Uani 1 1 d . . .
H8 H 0.5260 0.4926 0.1049 0.027 Uiso 1 1 calc R . .
C9 C 0.49130(7) 0.20399(16) 0.11935(8) 0.0195(2) Uani 1 1 d . . .
C10 C 0.40099(7) 0.24520(16) 0.10835(8) 0.0198(2) Uani 1 1 d . . .
C11 C 0.20602(7) 0.25604(17) 0.05905(9) 0.0213(2) Uani 1 1 d . . .
C12 C 0.16642(8) 0.34249(19) 0.11743(9) 0.0254(2) Uani 1 1 d . . .
H12 H 0.1735 0.2811 0.1837 0.030 Uiso 1 1 calc R . .
C13 C 0.10750(7) 0.60247(18) -0.00690(9) 0.0230(2) Uani 1 1 d . . .
C14 C 0.05803(9) 0.7773(2) -0.03170(10) 0.0312(3) Uani 1 1 d . . .
H14 H 0.0323 0.8261 0.0148 0.037 Uiso 1 1 calc R . .
C15 C 0.04706(9) 0.8785(2) -0.12518(11) 0.0331(3) Uani 1 1 d . . .
H15 H 0.0135 0.9983 -0.1430 0.040 Uiso 1 1 calc R . .
C16 C 0.08461(8) 0.8071(2) -0.19390(10) 0.0293(3) Uani 1 1 d . . .
H16 H 0.0770 0.8788 -0.2576 0.035 Uiso 1 1 calc R . .
C17 C 0.13274(8) 0.63209(18) -0.16899(9) 0.0239(2) Uani 1 1 d . . .
H17 H 0.1579 0.5833 -0.2161 0.029 Uiso 1 1 calc R . .
C18 C 0.14484(7) 0.52541(17) -0.07433(8) 0.0199(2) Uani 1 1 d . . .
C19 C 0.19537(7) 0.33789(17) -0.04599(9) 0.0206(2) Uani 1 1 d . . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.2224(14) . ?
O2 C3 1.3408(14) . ?
O2 C4 1.3843(14) . ?
O3 C10 1.2298(13) . ?
O4 C12 1.3500(14) . ?
O4 C13 1.3773(14) . ?
O5 C19 1.2317(13) . ?
C1 C2 1.4881(16) . ?
C1 C11 1.4986(15) . ?
C2 C3 1.3579(15) . ?
C2 C10 1.4641(15) . ?
C3 H3 0.9500 . ?
C4 C9 1.3908(15) . ?
C4 C5 1.3956(16) . ?
C5 C6 1.3795(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4041(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3827(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4025(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4762(15) . ?
C11 C12 1.3468(16) . ?
C11 C19 1.4658(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3913(16) . ?
C13 C18 1.3941(15) . ?
C14 C15 1.3804(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3979(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3812(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.4080(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.4722(15) . ?

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 O2 C4 118.56(9) . . ?
C12 O4 C13 118.34(9) . . ?
O1 C1 C2 121.55(10) . . ?
O1 C1 C11 119.83(10) . . ?
C2 C1 C11 118.56(10) . . ?
C3 C2 C10 120.19(10) . . ?
C3 C2 C1 116.65(10) . . ?
C10 C2 C1 123.05(10) . . ?
O2 C3 C2 124.98(10) . . ?
O2 C3 H3 117.5 . . ?
C2 C3 H3 117.5 . . ?
O2 C4 C9 121.68(10) . . ?
O2 C4 C5 116.30(10) . . ?
C9 C4 C5 122.02(11) . . ?
C6 C5 C4 118.49(11) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 120.93(11) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 119.61(11) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.63(11) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 118.32(10) . . ?
C4 C9 C10 120.46(10) . . ?
C8 C9 C10 121.22(10) . . ?
O3 C10 C2 124.19(10) . . ?
O3 C10 C9 121.69(10) . . ?
C2 C10 C9 114.11(9) . . ?
C12 C11 C19 120.82(10) . . ?
C12 C11 C1 116.75(10) . . ?
C19 C11 C1 122.42(10) . . ?
C11 C12 O4 124.58(10) . . ?
C11 C12 H12 117.7 . . ?
O4 C12 H12 117.7 . . ?
O4 C13 C14 115.93(10) . . ?
O4 C13 C18 122.07(10) . . ?
C14 C13 C18 122.00(11) . . ?
C15 C14 C13 118.66(12) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.87(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.90(11) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.49(11) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 118.07(10) . . ?
C13 C18 C19 120.22(10) . . ?
C17 C18 C19 121.71(10) . . ?
O5 C19 C11 123.49(10) . . ?
O5 C19 C18 122.67(10) . . ?
C11 C19 C18 113.80(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
O1 C1 C2 C3 20.30(16) . . . . ?
C11 C1 C2 C3 -162.61(10) . . . . ?
O1 C1 C2 C10 -155.96(11) . . . . ?
C11 C1 C2 C10 21.13(15) . . . . ?
C4 O2 C3 C2 0.77(16) . . . . ?
C10 C2 C3 O2 -1.43(17) . . . . ?
C1 C2 C3 O2 -177.81(10) . . . . ?
C3 O2 C4 C9 -0.41(15) . . . . ?
C3 O2 C4 C5 -179.67(10) . . . . ?
O2 C4 C5 C6 178.82(10) . . . . ?
C9 C4 C5 C6 -0.43(17) . . . . ?
C4 C5 C6 C7 0.02(17) . . . . ?
C5 C6 C7 C8 0.61(17) . . . . ?
C6 C7 C8 C9 -0.83(17) . . . . ?
O2 C4 C9 C8 -179.00(9) . . . . ?
C5 C4 C9 C8 0.22(16) . . . . ?
O2 C4 C9 C10 0.74(15) . . . . ?
C5 C4 C9 C10 179.95(10) . . . . ?
C7 C8 C9 C4 0.42(16) . . . . ?
C7 C8 C9 C10 -179.31(10) . . . . ?
C3 C2 C10 O3 -177.29(11) . . . . ?
C1 C2 C10 O3 -1.15(17) . . . . ?
C3 C2 C10 C9 1.59(14) . . . . ?
C1 C2 C10 C9 177.72(9) . . . . ?
C4 C9 C10 O3 177.63(10) . . . . ?
C8 C9 C10 O3 -2.64(16) . . . . ?
C4 C9 C10 C2 -1.27(14) . . . . ?
C8 C9 C10 C2 178.46(9) . . . . ?
O1 C1 C11 C12 47.48(15) . . . . ?
C2 C1 C11 C12 -129.66(11) . . . . ?
O1 C1 C11 C19 -132.45(12) . . . . ?
C2 C1 C11 C19 50.41(15) . . . . ?
C19 C11 C12 O4 -2.32(19) . . . . ?
C1 C11 C12 O4 177.75(11) . . . . ?
C13 O4 C12 C11 -0.84(18) . . . . ?
C12 O4 C13 C14 -178.56(11) . . . . ?
C12 O4 C13 C18 1.39(17) . . . . ?
O4 C13 C14 C15 178.88(12) . . . . ?
C18 C13 C14 C15 -1.07(19) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C18 -0.44(18) . . . . ?
O4 C13 C18 C17 -178.72(10) . . . . ?
C14 C13 C18 C17 1.22(17) . . . . ?
O4 C13 C18 C19 1.18(17) . . . . ?
C14 C13 C18 C19 -178.87(11) . . . . ?
C16 C17 C18 C13 -0.45(17) . . . . ?
C16 C17 C18 C19 179.64(11) . . . . ?
C12 C11 C19 O5 -173.24(11) . . . . ?
C1 C11 C19 O5 6.70(17) . . . . ?
C12 C11 C19 C18 4.52(15) . . . . ?
C1 C11 C19 C18 -175.54(9) . . . . ?
C13 C18 C19 O5 173.83(11) . . . . ?
C17 C18 C19 O5 -6.27(17) . . . . ?
C13 C18 C19 C11 -3.96(15) . . . . ?
C17 C18 C19 C11 175.95(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046

#=====================  End of is_mm62 =================================

#=====================  End of CIF submission =================================
####################################################################### 
# 
# 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_ah_mm2931
_database_code_depnum_ccdc_archive 'CCDC 1405372'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
3,3'-carbonylbis(6-methoxy-4H-chromen-4-one)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 O7'
_chemical_formula_sum            'C21 H14 O7'
_chemical_formula_weight         378.32

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9459(3)
_cell_length_b                   8.6534(4)
_cell_length_c                   14.8426(7)
_cell_angle_alpha                74.281(2)
_cell_angle_beta                 81.211(2)
_cell_angle_gamma                68.824(2)
_cell_volume                     799.27(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8275
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      30.01

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20387
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4243
_reflns_number_gt                3472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups).
 
 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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.2363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.83376(15) 0.78470(11) 0.72487(6) 0.0278(2) Uani 1 1 d . . . . .
O2 O 1.03438(13) 0.35665(12) 0.95285(6) 0.0257(2) Uani 1 1 d . . . . .
O3 O 0.46310(14) 0.03891(12) 1.11033(6) 0.0298(2) Uani 1 1 d . . . . .
O4 O 0.49272(13) 0.50625(11) 0.82492(6) 0.0256(2) Uani 1 1 d . . . . .
O5 O 0.70986(13) 0.71269(10) 0.48518(6) 0.01980(18) Uani 1 1 d . . . . .
O6 O 0.77588(14) 0.08596(11) 0.43832(6) 0.0241(2) Uani 1 1 d . . . . .
O7 O 0.86992(14) 0.29932(11) 0.70777(6) 0.0255(2) Uani 1 1 d . . . . .
C1 C 0.81240(17) 0.64784(15) 0.73185(8) 0.0194(2) Uani 1 1 d . . . . .
C3 C 0.99536(19) 0.47585(16) 0.87202(8) 0.0230(2) Uani 1 1 d . . . . .
H3 H 1.0948 0.5305 0.8467 0.028 Uiso 1 1 calc R U . . .
C4 C 0.88916(18) 0.27838(16) 0.99160(8) 0.0210(2) Uani 1 1 d . . . . .
C5 C 0.93931(19) 0.15027(17) 1.07220(9) 0.0255(3) Uani 1 1 d . . . . .
H5 H 1.0674 0.1205 1.0989 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8013(2) 0.06588(16) 1.11354(8) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.8356 -0.0241 1.1681 0.029 Uiso 1 1 calc R U . . .
C7 C 0.61026(19) 0.11326(16) 1.07474(8) 0.0222(2) Uani 1 1 d . . . . .
C8 C 0.56171(18) 0.24209(15) 0.99456(8) 0.0213(2) Uani 1 1 d . . . . .
H8 H 0.4318 0.2742 0.9689 0.026 Uiso 1 1 calc R U . . .
C9 C 0.70159(18) 0.32557(15) 0.95083(8) 0.0188(2) Uani 1 1 d . . . . .
C10 C 0.65761(18) 0.45584(15) 0.86252(8) 0.0188(2) Uani 1 1 d . . . . .
C11 C 0.82507(18) 0.52326(15) 0.82441(8) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.5038(2) -0.09551(17) 1.19251(9) 0.0304(3) Uani 1 1 d . . . . .
H12A H 0.3873 -0.1385 1.2090 0.046 Uiso 1 1 calc R U . . .
H12B H 0.5220 -0.0528 1.2443 0.046 Uiso 1 1 calc R U . . .
H12C H 0.6301 -0.1879 1.1809 0.046 Uiso 1 1 calc R U . . .
C13 C 0.78224(17) 0.59989(15) 0.64691(8) 0.0175(2) Uani 1 1 d . . . . .
C14 C 0.73672(17) 0.72832(15) 0.56910(8) 0.0190(2) Uani 1 1 d . . . . .
H14 H 0.7227 0.8388 0.5746 0.023 Uiso 1 1 calc R U . . .
C15 C 0.73250(16) 0.55281(14) 0.47539(8) 0.0170(2) Uani 1 1 d . . . . .
C16 C 0.70058(17) 0.54296(15) 0.38749(8) 0.0193(2) Uani 1 1 d . . . . .
H16 H 0.6683 0.6423 0.3377 0.023 Uiso 1 1 calc R U . . .
C17 C 0.71592(17) 0.38840(15) 0.37263(8) 0.0190(2) Uani 1 1 d . . . . .
H17 H 0.6936 0.3808 0.3127 0.023 Uiso 1 1 calc R U . . .
C18 C 0.76472(17) 0.24233(14) 0.44656(8) 0.0179(2) Uani 1 1 d . . . . .
C19 C 0.79868(17) 0.25286(15) 0.53406(8) 0.0178(2) Uani 1 1 d . . . . .
H19 H 0.8330 0.1533 0.5837 0.021 Uiso 1 1 calc R U . . .
C20 C 0.78258(16) 0.40956(14) 0.54945(7) 0.0164(2) Uani 1 1 d . . . . .
C21 C 0.81521(17) 0.42502(15) 0.64246(8) 0.0175(2) Uani 1 1 d . . . . .
C22 C 0.77380(19) 0.06732(16) 0.34528(8) 0.0231(3) Uani 1 1 d . . . . .
H22A H 0.6394 0.1387 0.3199 0.035 Uiso 1 1 calc R U . . .
H22B H 0.7971 -0.0522 0.3474 0.035 Uiso 1 1 calc R U . . .
H22C H 0.8835 0.1027 0.3051 0.035 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 1.2211(14) . ?
O2 C3 1.3429(15) . ?
O2 C4 1.3828(14) . ?
O3 C7 1.3652(15) . ?
O3 C12 1.4211(15) . ?
O4 C10 1.2312(13) . ?
O5 C14 1.3362(13) . ?
O5 C15 1.3801(13) . ?
O6 C18 1.3649(14) . ?
O6 C22 1.4359(13) . ?
O7 C21 1.2287(14) . ?
C1 C11 1.4909(16) . ?
C1 C13 1.4941(15) . ?
C3 C11 1.3471(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3825(17) . ?
C4 C9 1.3975(15) . ?
C5 C6 1.3828(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4046(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3802(16) . ?
C8 C9 1.3955(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4680(16) . ?
C10 C11 1.4573(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3532(16) . ?
C13 C21 1.4649(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3860(15) . ?
C15 C20 1.3903(15) . ?
C16 C17 1.3779(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.4032(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3870(15) . ?
C19 C20 1.3978(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.4808(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 O2 C4 118.39(9) . . ?
C7 O3 C12 118.34(10) . . ?
C14 O5 C15 118.17(9) . . ?
C18 O6 C22 116.81(9) . . ?
O1 C1 C11 120.55(10) . . ?
O1 C1 C13 120.34(10) . . ?
C11 C1 C13 119.05(10) . . ?
O2 C3 C11 124.55(11) . . ?
O2 C3 H3 117.7 . . ?
C11 C3 H3 117.7 . . ?
C5 C4 O2 116.75(10) . . ?
C5 C4 C9 121.64(11) . . ?
O2 C4 C9 121.61(11) . . ?
C4 C5 C6 119.39(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.94(11) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O3 C7 C8 115.42(10) . . ?
O3 C7 C6 124.54(11) . . ?
C8 C7 C6 120.04(11) . . ?
C7 C8 C9 120.63(10) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 118.33(11) . . ?
C8 C9 C10 121.33(10) . . ?
C4 C9 C10 120.31(10) . . ?
O4 C10 C11 122.93(11) . . ?
O4 C10 C9 123.16(10) . . ?
C11 C10 C9 113.90(10) . . ?
C3 C11 C10 121.01(11) . . ?
C3 C11 C1 117.98(10) . . ?
C10 C11 C1 121.01(10) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C21 120.19(10) . . ?
C14 C13 C1 115.57(10) . . ?
C21 C13 C1 124.06(10) . . ?
O5 C14 C13 125.43(10) . . ?
O5 C14 H14 117.3 . . ?
C13 C14 H14 117.3 . . ?
O5 C15 C16 116.20(10) . . ?
O5 C15 C20 122.16(10) . . ?
C16 C15 C20 121.64(10) . . ?
C17 C16 C15 119.69(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.66(10) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
O6 C18 C19 116.49(10) . . ?
O6 C18 C17 123.17(10) . . ?
C19 C18 C17 120.31(10) . . ?
C18 C19 C20 120.17(10) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.52(10) . . ?
C15 C20 C21 120.13(10) . . ?
C19 C20 C21 121.35(10) . . ?
O7 C21 C13 124.65(10) . . ?
O7 C21 C20 121.48(10) . . ?
C13 C21 C20 113.85(10) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C4 O2 C3 C11 -1.28(18) . . . . ?
C3 O2 C4 C5 176.78(11) . . . . ?
C3 O2 C4 C9 -2.72(17) . . . . ?
O2 C4 C5 C6 -179.23(11) . . . . ?
C9 C4 C5 C6 0.27(19) . . . . ?
C4 C5 C6 C7 -1.41(19) . . . . ?
C12 O3 C7 C8 179.58(11) . . . . ?
C12 O3 C7 C6 0.23(18) . . . . ?
C5 C6 C7 O3 -179.65(12) . . . . ?
C5 C6 C7 C8 1.03(19) . . . . ?
O3 C7 C8 C9 -178.87(11) . . . . ?
C6 C7 C8 C9 0.51(18) . . . . ?
C7 C8 C9 C4 -1.61(17) . . . . ?
C7 C8 C9 C10 176.36(11) . . . . ?
C5 C4 C9 C8 1.24(18) . . . . ?
O2 C4 C9 C8 -179.29(10) . . . . ?
C5 C4 C9 C10 -176.76(11) . . . . ?
O2 C4 C9 C10 2.71(18) . . . . ?
C8 C9 C10 O4 4.38(18) . . . . ?
C4 C9 C10 O4 -177.68(11) . . . . ?
C8 C9 C10 C11 -177.00(10) . . . . ?
C4 C9 C10 C11 0.94(16) . . . . ?
O2 C3 C11 C10 5.15(19) . . . . ?
O2 C3 C11 C1 -175.31(11) . . . . ?
O4 C10 C11 C3 173.92(11) . . . . ?
C9 C10 C11 C3 -4.69(16) . . . . ?
O4 C10 C11 C1 -5.60(18) . . . . ?
C9 C10 C11 C1 175.78(10) . . . . ?
O1 C1 C11 C3 -54.40(16) . . . . ?
C13 C1 C11 C3 122.99(12) . . . . ?
O1 C1 C11 C10 125.13(12) . . . . ?
C13 C1 C11 C10 -57.47(15) . . . . ?
O1 C1 C13 C14 -13.54(16) . . . . ?
C11 C1 C13 C14 169.06(10) . . . . ?
O1 C1 C13 C21 161.41(11) . . . . ?
C11 C1 C13 C21 -15.99(16) . . . . ?
C15 O5 C14 C13 -0.91(16) . . . . ?
C21 C13 C14 O5 2.73(18) . . . . ?
C1 C13 C14 O5 177.89(10) . . . . ?
C14 O5 C15 C16 179.18(10) . . . . ?
C14 O5 C15 C20 -0.24(15) . . . . ?
O5 C15 C16 C17 -178.60(10) . . . . ?
C20 C15 C16 C17 0.83(17) . . . . ?
C15 C16 C17 C18 -0.31(17) . . . . ?
C22 O6 C18 C19 -170.40(10) . . . . ?
C22 O6 C18 C17 11.42(16) . . . . ?
C16 C17 C18 O6 177.73(10) . . . . ?
C16 C17 C18 C19 -0.39(17) . . . . ?
O6 C18 C19 C20 -177.64(10) . . . . ?
C17 C18 C19 C20 0.60(17) . . . . ?
O5 C15 C20 C19 178.78(10) . . . . ?
C16 C15 C20 C19 -0.61(16) . . . . ?
O5 C15 C20 C21 -0.50(16) . . . . ?
C16 C15 C20 C21 -179.89(10) . . . . ?
C18 C19 C20 C15 -0.10(16) . . . . ?
C18 C19 C20 C21 179.17(10) . . . . ?
C14 C13 C21 O7 175.12(11) . . . . ?
C1 C13 C21 O7 0.39(18) . . . . ?
C14 C13 C21 C20 -3.14(15) . . . . ?
C1 C13 C21 C20 -177.87(10) . . . . ?
C15 C20 C21 O7 -176.22(10) . . . . ?
C19 C20 C21 O7 4.52(17) . . . . ?
C15 C20 C21 C13 2.10(15) . . . . ?
C19 C20 C21 C13 -177.16(10) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

