# Electronic Supplementary Material (ESI) for ChemComm.
# 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_CBA13-11
_database_code_depnum_ccdc_archive 'CCDC 1469782'

_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
#============================================================================== 
# CBA13-11
#==============================================================================
_audit_creation_date             'August 21 2014'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
11-Benzoyl-6-hydroxytetracen-5(12H)-one
;
_chemical_name_common            ?
_chemical_melting_point          178
_chemical_formula_moiety         'C25 H16 O3'
_chemical_formula_sum            'C25 H16 O3'
_chemical_formula_weight         364.38
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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   'C 2/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'
'-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                   25.507(4)
_cell_length_b                   8.1552(14)
_cell_length_c                   16.661(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.869(2)
_cell_angle_gamma                90.00
_cell_volume                     3461.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2632
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.46
_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8153
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3046
_reflns_number_gt                2504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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. 
;

_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)+(0.0404P)²+1.9447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3046
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23184(5) 0.69087(17) 0.34501(8) 0.0164(3) Uani 1 1 d . . .
C2 C 0.21794(5) 0.62204(17) 0.42270(8) 0.0157(3) Uani 1 1 d . . .
C3 C 0.16767(6) 0.64941(18) 0.45000(9) 0.0193(3) Uani 1 1 d . . .
H3 H 0.1431 0.7124 0.4183 0.023 Uiso 1 1 calc R . .
C4 C 0.15352(6) 0.58568(18) 0.52244(9) 0.0216(3) Uani 1 1 d . . .
H4 H 0.1194 0.6050 0.5410 0.026 Uiso 1 1 calc R . .
C5 C 0.18979(6) 0.49265(18) 0.56816(9) 0.0216(3) Uani 1 1 d . . .
H5 H 0.1803 0.4481 0.6181 0.026 Uiso 1 1 calc R . .
C6 C 0.23944(6) 0.46469(17) 0.54148(9) 0.0195(3) Uani 1 1 d . . .
H6 H 0.2637 0.4007 0.5733 0.023 Uiso 1 1 calc R . .
C7 C 0.25444(5) 0.52908(17) 0.46852(8) 0.0162(3) Uani 1 1 d . . .
C8 C 0.30900(5) 0.49720(17) 0.44188(8) 0.0163(3) Uani 1 1 d . . .
H8A H 0.3143 0.3771 0.4398 0.020 Uiso 1 1 calc R . .
H8B H 0.3343 0.5412 0.4834 0.020 Uiso 1 1 calc R . .
C9 C 0.32232(5) 0.56833(16) 0.36176(8) 0.0143(3) Uani 1 1 d . . .
C10 C 0.37108(5) 0.54236(17) 0.33222(8) 0.0153(3) Uani 1 1 d . . .
C11 C 0.38286(5) 0.59758(17) 0.25347(8) 0.0160(3) Uani 1 1 d . . .
C12 C 0.43114(6) 0.56509(18) 0.21839(9) 0.0194(3) Uani 1 1 d . . .
H12 H 0.4573 0.5041 0.2479 0.023 Uiso 1 1 calc R . .
C13 C 0.44103(6) 0.61957(18) 0.14290(9) 0.0210(3) Uani 1 1 d . . .
H13 H 0.4734 0.5933 0.1203 0.025 Uiso 1 1 calc R . .
C14 C 0.40366(6) 0.71398(18) 0.09848(9) 0.0196(3) Uani 1 1 d . . .
H14 H 0.4112 0.7537 0.0467 0.024 Uiso 1 1 calc R . .
C15 C 0.35659(6) 0.74822(17) 0.13015(8) 0.0174(3) Uani 1 1 d . . .
H15 H 0.3314 0.8121 0.1001 0.021 Uiso 1 1 calc R . .
C16 C 0.34490(5) 0.68971(16) 0.20721(8) 0.0156(3) Uani 1 1 d . . .
C17 C 0.29556(5) 0.72056(16) 0.23995(8) 0.0150(3) Uani 1 1 d . . .
C18 C 0.28378(5) 0.65945(16) 0.31523(8) 0.0147(3) Uani 1 1 d . . .
C19 C 0.41447(5) 0.46699(18) 0.38556(8) 0.0169(3) Uani 1 1 d . . .
C20 C 0.43380(5) 0.29874(17) 0.36857(8) 0.0173(3) Uani 1 1 d . . .
C21 C 0.40840(6) 0.20003(18) 0.31040(9) 0.0199(3) Uani 1 1 d . . .
H21 H 0.3788 0.2410 0.2798 0.024 Uiso 1 1 calc R . .
C22 C 0.42628(6) 0.04200(18) 0.29708(10) 0.0252(4) Uani 1 1 d . . .
H22 H 0.4087 -0.0256 0.2578 0.030 Uiso 1 1 calc R . .
C23 C 0.46975(6) -0.0168(2) 0.34114(10) 0.0281(4) Uani 1 1 d . . .
H23 H 0.4818 -0.1253 0.3323 0.034 Uiso 1 1 calc R . .
C24 C 0.47806(6) 0.23885(19) 0.41231(9) 0.0210(3) Uani 1 1 d . . .
H24 H 0.4958 0.3059 0.4516 0.025 Uiso 1 1 calc R . .
C25 C 0.49579(6) 0.0816(2) 0.39810(10) 0.0267(4) Uani 1 1 d . . .
H25 H 0.5259 0.0409 0.4275 0.032 Uiso 1 1 calc R . .
O1 O 0.26085(4) 0.80846(12) 0.19490(6) 0.0201(2) Uani 1 1 d . . .
O2 O 0.19904(4) 0.77598(12) 0.30518(6) 0.0215(3) Uani 1 1 d . . .
O3 O 0.43334(4) 0.54713(13) 0.44188(6) 0.0234(3) Uani 1 1 d . . .
H1 H 0.2300(7) 0.814(2) 0.2284(11) 0.035 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.2515(17) . ?
C1 C18 1.460(2) . ?
C1 C2 1.470(2) . ?
C2 C7 1.398(2) . ?
C2 C3 1.3999(19) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.5043(19) . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.377(2) . ?
C9 C18 1.4294(19) . ?
C10 C11 1.433(2) . ?
C10 C19 1.5146(19) . ?
C11 C12 1.414(2) . ?
C11 C16 1.4219(19) . ?
C12 C13 1.369(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.364(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.419(2) . ?
C17 O1 1.3396(17) . ?
C17 C18 1.396(2) . ?
C19 O3 1.2223(17) . ?
C19 C20 1.490(2) . ?
C20 C21 1.394(2) . ?
C20 C24 1.401(2) . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C25 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O1 H1 0.987(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 C18 120.72(13) . . ?
O2 C1 C2 119.62(13) . . ?
C18 C1 C2 119.66(12) . . ?
C7 C2 C3 120.34(13) . . ?
C7 C2 C1 120.30(13) . . ?
C3 C2 C1 119.36(13) . . ?
C4 C3 C2 120.57(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.22(14) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.54(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.93(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 118.41(13) . . ?
C6 C7 C8 119.36(13) . . ?
C2 C7 C8 122.24(13) . . ?
C7 C8 C9 116.54(12) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C18 119.68(13) . . ?
C10 C9 C8 120.28(12) . . ?
C18 C9 C8 120.02(12) . . ?
C9 C10 C11 120.90(13) . . ?
C9 C10 C19 119.96(12) . . ?
C11 C10 C19 118.95(12) . . ?
C12 C11 C16 117.30(13) . . ?
C12 C11 C10 123.11(13) . . ?
C16 C11 C10 119.59(13) . . ?
C13 C12 C11 121.53(13) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 120.65(14) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.66(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.75(13) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 121.35(13) . . ?
C15 C16 C11 120.07(13) . . ?
C17 C16 C11 118.59(13) . . ?
O1 C17 C18 121.90(13) . . ?
O1 C17 C16 116.97(12) . . ?
C18 C17 C16 121.13(13) . . ?
C17 C18 C9 119.98(13) . . ?
C17 C18 C1 118.83(13) . . ?
C9 C18 C1 121.19(13) . . ?
O3 C19 C20 121.12(13) . . ?
O3 C19 C10 118.79(13) . . ?
C20 C19 C10 120.08(12) . . ?
C21 C20 C24 119.65(14) . . ?
C21 C20 C19 121.13(13) . . ?
C24 C20 C19 119.21(13) . . ?
C22 C21 C20 120.13(14) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.85(15) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C25 120.37(15) . . ?
C22 C23 H23 119.8 . . ?
C25 C23 H23 119.8 . . ?
C25 C24 C20 119.72(14) . . ?
C25 C24 H24 120.1 . . ?
C20 C24 H24 120.1 . . ?
C24 C25 C23 120.26(15) . . ?
C24 C25 H25 119.9 . . ?
C23 C25 H25 119.9 . . ?
C17 O1 H1 103.4(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_CBA13-9b
_database_code_depnum_ccdc_archive 'CCDC 1469783'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

#============================================================================== 
# CBA13-9b
#==============================================================================
_audit_creation_date             '01 May 2013'
_audit_creation_method           SHELXL-97

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

#  CHEMICAL DATA

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

_chemical_name_systematic        
; 
Ethyl 4-benzoyl-3-benzyl-1-hydroxy-2-naphthoate
;
_chemical_name_common            ?
_chemical_melting_point          133
_chemical_formula_moiety         'C27 H22 O4'
_chemical_formula_sum            'C27 H22 O4'
_chemical_formula_weight         410.45
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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           triclinic
_symmetry_space_group_name_H-M   'P -1      '
_symmetry_space_group_name_Hall  '-P 1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.173(2)
_cell_length_b                   10.382(3)
_cell_length_c                   12.748(3)
_cell_angle_alpha                104.062(3)
_cell_angle_beta                 94.660(3)
_cell_angle_gamma                116.023(2)
_cell_volume                     1033.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4575
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.52
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           
; 
 ? 
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10078
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3635
_reflns_number_gt                3133
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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. 
;

_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)+(0.0829P)²+0.2205P] 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         3635
_refine_ls_number_parameters     282
_refine_ls_number_restraints     204
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.19475(18) 0.02295(16) 0.11873(11) 0.0183(3) Uani 1 1 d U . .
C2 C 0.34378(18) 0.16178(16) 0.17094(11) 0.0194(3) Uani 1 1 d U . .
C3 C 0.49849(18) 0.18332(17) 0.14539(13) 0.0244(3) Uani 1 1 d U . .
H3 H 0.5050 0.1040 0.0937 0.029 Uiso 1 1 calc R . .
C4 C 0.63925(19) 0.31853(18) 0.19509(14) 0.0283(4) Uani 1 1 d U . .
H4 H 0.7425 0.3334 0.1765 0.034 Uiso 1 1 calc R . .
C5 C 0.63085(19) 0.43504(18) 0.27348(13) 0.0290(4) Uani 1 1 d U . .
H5 H 0.7291 0.5278 0.3084 0.035 Uiso 1 1 calc R . .
C6 C 0.48275(18) 0.41635(17) 0.30003(12) 0.0251(4) Uani 1 1 d U . .
H6 H 0.4796 0.4963 0.3534 0.030 Uiso 1 1 calc R . .
C7 C 0.33389(17) 0.27933(16) 0.24897(11) 0.0191(3) Uani 1 1 d U . .
C8 C 0.17608(17) 0.25659(15) 0.27187(11) 0.0175(3) Uani 1 1 d U . .
C9 C 0.03144(17) 0.12563(15) 0.21907(11) 0.0167(3) Uani 1 1 d U . .
C10 C 0.04059(17) 0.00292(15) 0.14041(11) 0.0172(3) Uani 1 1 d U . .
C11 C 0.17317(17) 0.38203(15) 0.36140(11) 0.0190(3) Uani 1 1 d U . .
C12 C 0.14235(16) 0.49869(15) 0.32964(11) 0.0176(3) Uani 1 1 d U . .
C13 C 0.11991(17) 0.49680(15) 0.21985(12) 0.0202(3) Uani 1 1 d U . .
H13 H 0.1256 0.4211 0.1636 0.024 Uiso 1 1 calc R . .
C14 C 0.08918(18) 0.60535(17) 0.19249(12) 0.0240(3) Uani 1 1 d U . .
H14 H 0.0737 0.6042 0.1176 0.029 Uiso 1 1 calc R . .
C15 C 0.08115(18) 0.71559(16) 0.27508(13) 0.0244(3) Uani 1 1 d U . .
H15 H 0.0596 0.7896 0.2562 0.029 Uiso 1 1 calc R . .
C16 C 0.10411(17) 0.71927(16) 0.38473(12) 0.0223(3) Uani 1 1 d U . .
H16 H 0.0990 0.7957 0.4406 0.027 Uiso 1 1 calc R . .
C17 C 0.13454(17) 0.61079(15) 0.41261(12) 0.0198(3) Uani 1 1 d U . .
H17 H 0.1500 0.6125 0.4876 0.024 Uiso 1 1 calc R . .
C18 C -0.13079(17) 0.11704(15) 0.24422(12) 0.0185(3) Uani 1 1 d U . .
H18A H -0.2108 0.0780 0.1729 0.022 Uiso 1 1 calc R . .
H18B H -0.1105 0.2209 0.2807 0.022 Uiso 1 1 calc R . .
C19 C -0.21284(17) 0.02080(15) 0.31655(11) 0.0189(3) Uani 1 1 d U . .
C20 C -0.36881(18) 0.00019(17) 0.33334(12) 0.0245(3) Uani 1 1 d U . .
H20 H -0.4192 0.0489 0.3019 0.029 Uiso 1 1 calc R . .
C21 C -0.45134(19) -0.09090(18) 0.39558(13) 0.0298(4) Uani 1 1 d U . .
H21 H -0.5584 -0.1054 0.4054 0.036 Uiso 1 1 calc R . .
C22 C -0.3788(2) -0.16035(17) 0.44313(13) 0.0296(4) Uani 1 1 d U . .
H22 H -0.4356 -0.2224 0.4857 0.035 Uiso 1 1 calc R . .
C23 C -0.2225(2) -0.13928(17) 0.42862(13) 0.0275(4) Uani 1 1 d U . .
H23 H -0.1718 -0.1867 0.4613 0.033 Uiso 1 1 calc R . .
C24 C -0.14010(18) -0.04818(16) 0.36584(12) 0.0217(3) Uani 1 1 d U . .
H24 H -0.0326 -0.0332 0.3567 0.026 Uiso 1 1 calc R . .
C25 C -0.10386(18) -0.14711(15) 0.08298(11) 0.0182(3) Uani 1 1 d U . .
C26 C -0.38938(18) -0.31591(16) 0.05604(13) 0.0244(4) Uani 1 1 d U . .
H26A H -0.3641 -0.3877 0.0821 0.029 Uiso 1 1 calc R . .
H26B H -0.4118 -0.3485 -0.0259 0.029 Uiso 1 1 calc R . .
C27 C -0.5379(2) -0.31129(18) 0.09593(14) 0.0351(4) Uani 1 1 d U . .
H27A H -0.5177 -0.2869 0.1767 0.053 Uiso 1 1 calc R . .
H27B H -0.6365 -0.4099 0.0623 0.053 Uiso 1 1 calc R . .
H27C H -0.5562 -0.2340 0.0747 0.053 Uiso 1 1 calc R . .
O1 O -0.09046(13) -0.25258(11) 0.02283(8) 0.0232(3) Uani 1 1 d U . .
O2 O 0.21480(13) -0.08459(11) 0.04791(8) 0.0240(3) Uani 1 1 d U . .
H2 H 0.1225 -0.1625 0.0214 0.036 Uiso 1 1 calc R . .
O3 O 0.19929(15) 0.38724(12) 0.45773(8) 0.0308(3) Uani 1 1 d U . .
O4 O -0.24964(12) -0.16315(11) 0.10152(8) 0.0220(3) Uani 1 1 d U . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.3464(17) . ?
C1 C10 1.397(2) . ?
C1 C2 1.430(2) . ?
C2 C3 1.415(2) . ?
C2 C7 1.417(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.428(2) . ?
C8 C9 1.3745(19) . ?
C8 C11 1.5207(19) . ?
C9 C10 1.4568(19) . ?
C9 C18 1.5167(19) . ?
C10 C25 1.4815(19) . ?
C11 O3 1.2153(17) . ?
C11 C12 1.494(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.4020(19) . ?
C13 C14 1.387(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.5217(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.387(2) . ?
C19 C20 1.394(2) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O1 1.2359(17) . ?
C25 O4 1.3217(17) . ?
C26 O4 1.4640(16) . ?
C26 C27 1.509(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O2 H2 0.8400 . ?

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
O2 C1 C10 123.26(13) . . ?
O2 C1 C2 115.15(12) . . ?
C10 C1 C2 121.60(13) . . ?
C3 C2 C7 120.08(13) . . ?
C3 C2 C1 121.29(13) . . ?
C7 C2 C1 118.62(13) . . ?
C4 C3 C2 120.20(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.06(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.72(14) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.95(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 117.96(13) . . ?
C2 C7 C8 119.25(12) . . ?
C6 C7 C8 122.78(13) . . ?
C9 C8 C7 122.49(12) . . ?
C9 C8 C11 120.15(12) . . ?
C7 C8 C11 117.32(12) . . ?
C8 C9 C10 118.69(13) . . ?
C8 C9 C18 118.19(12) . . ?
C10 C9 C18 123.12(12) . . ?
C1 C10 C9 119.28(12) . . ?
C1 C10 C25 116.42(12) . . ?
C9 C10 C25 124.26(12) . . ?
O3 C11 C12 121.19(12) . . ?
O3 C11 C8 119.36(12) . . ?
C12 C11 C8 119.44(12) . . ?
C13 C12 C17 119.92(13) . . ?
C13 C12 C11 121.26(12) . . ?
C17 C12 C11 118.81(13) . . ?
C14 C13 C12 120.05(13) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.64(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.91(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.72(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 119.75(13) . . ?
C16 C17 H17 120.1 . . ?
C12 C17 H17 120.1 . . ?
C9 C18 C19 117.11(11) . . ?
C9 C18 H18A 108.0 . . ?
C19 C18 H18A 108.0 . . ?
C9 C18 H18B 108.0 . . ?
C19 C18 H18B 108.0 . . ?
H18A C18 H18B 107.3 . . ?
C24 C19 C20 118.51(13) . . ?
C24 C19 C18 123.04(13) . . ?
C20 C19 C18 118.45(13) . . ?
C21 C20 C19 120.62(15) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.40(14) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.73(14) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 119.78(15) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 120.92(14) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
O1 C25 O4 121.38(12) . . ?
O1 C25 C10 122.78(13) . . ?
O4 C25 C10 115.83(12) . . ?
O4 C26 C27 107.01(12) . . ?
O4 C26 H26A 110.3 . . ?
C27 C26 H26A 110.3 . . ?
O4 C26 H26B 110.3 . . ?
C27 C26 H26B 110.3 . . ?
H26A C26 H26B 108.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C25 O4 C26 115.93(11) . . ?

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
O2 C1 C2 C3 2.2(2) . . . . ?
C10 C1 C2 C3 -177.52(12) . . . . ?
O2 C1 C2 C7 -178.30(12) . . . . ?
C10 C1 C2 C7 2.0(2) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 178.80(13) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
C1 C2 C7 C6 -179.98(13) . . . . ?
C3 C2 C7 C8 178.65(13) . . . . ?
C1 C2 C7 C8 -0.85(19) . . . . ?
C5 C6 C7 C2 0.9(2) . . . . ?
C5 C6 C7 C8 -178.16(13) . . . . ?
C2 C7 C8 C9 -1.6(2) . . . . ?
C6 C7 C8 C9 177.50(13) . . . . ?
C2 C7 C8 C11 176.23(12) . . . . ?
C6 C7 C8 C11 -4.7(2) . . . . ?
C7 C8 C9 C10 2.8(2) . . . . ?
C11 C8 C9 C10 -174.93(12) . . . . ?
C7 C8 C9 C18 -176.14(12) . . . . ?
C11 C8 C9 C18 6.11(19) . . . . ?
O2 C1 C10 C9 179.56(12) . . . . ?
C2 C1 C10 C9 -0.7(2) . . . . ?
O2 C1 C10 C25 1.6(2) . . . . ?
C2 C1 C10 C25 -178.71(12) . . . . ?
C8 C9 C10 C1 -1.64(19) . . . . ?
C18 C9 C10 C1 177.26(12) . . . . ?
C8 C9 C10 C25 176.16(12) . . . . ?
C18 C9 C10 C25 -4.9(2) . . . . ?
C9 C8 C11 O3 93.29(17) . . . . ?
C7 C8 C11 O3 -84.57(16) . . . . ?
C9 C8 C11 C12 -88.18(16) . . . . ?
C7 C8 C11 C12 93.96(15) . . . . ?
O3 C11 C12 C13 177.04(13) . . . . ?
C8 C11 C12 C13 -1.46(19) . . . . ?
O3 C11 C12 C17 -3.6(2) . . . . ?
C8 C11 C12 C17 177.91(12) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 179.11(13) . . . . ?
C12 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C16 C17 C12 0.2(2) . . . . ?
C13 C12 C17 C16 0.1(2) . . . . ?
C11 C12 C17 C16 -179.26(12) . . . . ?
C8 C9 C18 C19 -106.09(15) . . . . ?
C10 C9 C18 C19 75.00(17) . . . . ?
C9 C18 C19 C24 4.93(19) . . . . ?
C9 C18 C19 C20 -174.59(12) . . . . ?
C24 C19 C20 C21 -1.8(2) . . . . ?
C18 C19 C20 C21 177.78(13) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C20 C19 C24 C23 1.6(2) . . . . ?
C18 C19 C24 C23 -177.95(13) . . . . ?
C22 C23 C24 C19 -0.7(2) . . . . ?
C1 C10 C25 O1 3.3(2) . . . . ?
C9 C10 C25 O1 -174.61(13) . . . . ?
C1 C10 C25 O4 -178.00(11) . . . . ?
C9 C10 C25 O4 4.1(2) . . . . ?
O1 C25 O4 C26 5.96(19) . . . . ?
C10 C25 O4 C26 -172.80(11) . . . . ?
C27 C26 O4 C25 174.63(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_CBA13-9a
_database_code_depnum_ccdc_archive 'CCDC 1469784'

_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
#============================================================================== 
# CBA13-9a
#==============================================================================
_audit_creation_date             'June 9 2014'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 4-benzoyl-1-hydroxy-3-pentyl-2-naphthoate
;
_chemical_name_common            ?
_chemical_melting_point          90.5
_chemical_formula_moiety         'C25 H26 O4'
_chemical_formula_sum            'C25 H26 O4'
_chemical_formula_weight         390.46
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.1779(17)
_cell_length_b                   7.8527(9)
_cell_length_c                   19.280(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.4640(16)
_cell_angle_gamma                90.00
_cell_volume                     2132.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4024
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.64
_exptl_crystal_description       block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10003
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3758
_reflns_number_gt                3224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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. 
;

_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+0.5033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3758
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49154(9) 0.15050(15) 0.42111(7) 0.0166(3) Uani 1 1 d . . .
C2 C 0.43176(9) 0.11445(15) 0.35824(6) 0.0169(3) Uani 1 1 d . . .
C3 C 0.47019(9) 0.05633(16) 0.29786(7) 0.0207(3) Uani 1 1 d . . .
H3 H 0.5365 0.0366 0.2994 0.025 Uiso 1 1 calc R . .
C4 C 0.41229(9) 0.02854(18) 0.23736(7) 0.0242(3) Uani 1 1 d . . .
H4 H 0.4383 -0.0109 0.1970 0.029 Uiso 1 1 calc R . .
C5 C 0.31390(10) 0.05836(18) 0.23478(7) 0.0246(3) Uani 1 1 d . . .
H5 H 0.2741 0.0405 0.1924 0.030 Uiso 1 1 calc R . .
C6 C 0.27509(9) 0.11276(17) 0.29279(7) 0.0218(3) Uani 1 1 d . . .
H6 H 0.2086 0.1322 0.2901 0.026 Uiso 1 1 calc R . .
C7 C 0.33278(9) 0.14055(15) 0.35682(6) 0.0170(3) Uani 1 1 d . . .
C8 C 0.29509(9) 0.19245(15) 0.41947(6) 0.0162(3) Uani 1 1 d . . .
C9 C 0.35256(9) 0.22430(15) 0.48051(6) 0.0157(3) Uani 1 1 d . . .
C10 C 0.45443(9) 0.21023(15) 0.48089(6) 0.0158(3) Uani 1 1 d . . .
C11 C 0.52574(9) 0.25654(15) 0.54019(6) 0.0164(3) Uani 1 1 d . . .
C12 C 0.56546(9) 0.39735(17) 0.64790(7) 0.0208(3) Uani 1 1 d . . .
H12A H 0.6063 0.4841 0.6289 0.025 Uiso 1 1 calc R . .
H12B H 0.6060 0.3016 0.6667 0.025 Uiso 1 1 calc R . .
C13 C 0.51363(10) 0.47342(18) 0.70428(7) 0.0257(3) Uani 1 1 d . . .
H13A H 0.4691 0.5603 0.6840 0.039 Uiso 1 1 calc R . .
H13B H 0.5594 0.5258 0.7398 0.039 Uiso 1 1 calc R . .
H13C H 0.4785 0.3838 0.7258 0.039 Uiso 1 1 calc R . .
C14 C 0.18884(9) 0.21639(16) 0.41633(6) 0.0166(3) Uani 1 1 d . . .
C15 C 0.12549(9) 0.06520(16) 0.41687(6) 0.0174(3) Uani 1 1 d . . .
C16 C 0.16225(9) -0.09869(17) 0.42741(7) 0.0215(3) Uani 1 1 d . . .
H16 H 0.2290 -0.1159 0.4335 0.026 Uiso 1 1 calc R . .
C17 C 0.10134(10) -0.23653(17) 0.42895(8) 0.0270(3) Uani 1 1 d . . .
H17 H 0.1263 -0.3482 0.4362 0.032 Uiso 1 1 calc R . .
C18 C 0.00405(10) -0.21129(18) 0.41984(8) 0.0303(3) Uani 1 1 d . . .
H18 H -0.0375 -0.3058 0.4213 0.036 Uiso 1 1 calc R . .
C19 C -0.03315(10) -0.04873(19) 0.40855(8) 0.0292(3) Uani 1 1 d . . .
H19 H -0.0999 -0.0323 0.4017 0.035 Uiso 1 1 calc R . .
C20 C 0.02724(9) 0.08909(17) 0.40732(7) 0.0229(3) Uani 1 1 d . . .
H20 H 0.0019 0.2004 0.4000 0.027 Uiso 1 1 calc R . .
C21 C 0.30559(9) 0.26485(16) 0.54564(6) 0.0170(3) Uani 1 1 d . . .
H21A H 0.3454 0.2178 0.5866 0.020 Uiso 1 1 calc R . .
H21B H 0.2435 0.2061 0.5423 0.020 Uiso 1 1 calc R . .
C22 C 0.28961(9) 0.45490(16) 0.55824(6) 0.0183(3) Uani 1 1 d . . .
H22A H 0.3511 0.5157 0.5604 0.022 Uiso 1 1 calc R . .
H22B H 0.2471 0.5022 0.5187 0.022 Uiso 1 1 calc R . .
C23 C 0.24580(9) 0.48466(17) 0.62591(7) 0.0209(3) Uani 1 1 d . . .
H23A H 0.1875 0.4149 0.6251 0.025 Uiso 1 1 calc R . .
H23B H 0.2909 0.4451 0.6655 0.025 Uiso 1 1 calc R . .
C24 C 0.22084(10) 0.66936(18) 0.63813(7) 0.0274(3) Uani 1 1 d . . .
H24A H 0.1757 0.7094 0.5986 0.033 Uiso 1 1 calc R . .
H24B H 0.2791 0.7394 0.6392 0.033 Uiso 1 1 calc R . .
C25 C 0.17700(11) 0.6961(2) 0.70574(8) 0.0370(4) Uani 1 1 d . . .
H25A H 0.1179 0.6309 0.7043 0.056 Uiso 1 1 calc R . .
H25B H 0.1634 0.8174 0.7114 0.056 Uiso 1 1 calc R . .
H25C H 0.2214 0.6574 0.7452 0.056 Uiso 1 1 calc R . .
O1 O 0.58459(6) 0.12457(12) 0.41759(5) 0.0204(2) Uani 1 1 d . . .
H1O H 0.6133(10) 0.1530(18) 0.4613(8) 0.025 Uiso 1 1 d . . .
O2 O 0.61130(6) 0.22869(11) 0.54030(5) 0.0214(2) Uani 1 1 d . . .
O3 O 0.49311(6) 0.33683(11) 0.59320(4) 0.0196(2) Uani 1 1 d . . .
O4 O 0.15568(6) 0.36027(11) 0.41238(5) 0.0220(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3442(15) . ?
C1 C10 1.4006(18) . ?
C1 C2 1.4272(18) . ?
C2 C3 1.4153(18) . ?
C2 C7 1.4154(17) . ?
C3 C4 1.3662(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4098(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3691(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4189(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4339(17) . ?
C8 C9 1.3767(17) . ?
C8 C14 1.5125(17) . ?
C9 C10 1.4478(17) . ?
C9 C21 1.5199(17) . ?
C10 C11 1.4836(17) . ?
C11 O2 1.2324(15) . ?
C11 O3 1.3276(15) . ?
C12 O3 1.4653(15) . ?
C12 C13 1.5027(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O4 1.2228(15) . ?
C14 C15 1.4895(18) . ?
C15 C20 1.3971(17) . ?
C15 C16 1.3948(18) . ?
C16 C17 1.3871(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.5330(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5247(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5177(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.521(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O1 H1O 0.921(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 123.64(11) . . ?
O1 C1 C2 114.80(11) . . ?
C10 C1 C2 121.55(11) . . ?
C3 C2 C7 120.24(11) . . ?
C3 C2 C1 121.05(12) . . ?
C7 C2 C1 118.71(11) . . ?
C4 C3 C2 120.25(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.05(12) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.67(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.89(12) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 117.88(12) . . ?
C2 C7 C8 119.18(11) . . ?
C6 C7 C8 122.94(12) . . ?
C9 C8 C7 122.07(11) . . ?
C9 C8 C14 120.17(11) . . ?
C7 C8 C14 117.74(10) . . ?
C8 C9 C10 118.99(11) . . ?
C8 C9 C21 118.17(11) . . ?
C10 C9 C21 122.78(10) . . ?
C1 C10 C9 119.23(11) . . ?
C1 C10 C11 115.45(11) . . ?
C9 C10 C11 125.32(11) . . ?
O2 C11 O3 120.74(11) . . ?
O2 C11 C10 122.89(11) . . ?
O3 C11 C10 116.32(10) . . ?
O3 C12 C13 106.85(10) . . ?
O3 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O3 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C15 120.59(11) . . ?
O4 C14 C8 119.45(11) . . ?
C15 C14 C8 119.95(10) . . ?
C20 C15 C16 119.59(12) . . ?
C20 C15 C14 119.02(11) . . ?
C16 C15 C14 121.38(11) . . ?
C17 C16 C15 119.99(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.95(13) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.43(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.83(13) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.20(12) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C9 C21 C22 114.91(10) . . ?
C9 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
C9 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C21 111.50(10) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 113.83(11) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 112.97(12) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 O1 H1O 104.6(9) . . ?
C11 O3 C12 115.58(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_CBA13-12
_database_code_depnum_ccdc_archive 'CCDC 1473607'

_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {20848805-d9ce-453c-a0fd-84662ea1e729}
#============================================================================== 
# CBA13-12
#==============================================================================
_audit_creation_date             'july 18 2013'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
Ethyl 5-hydroxy-12-phenyltetraphene-6-carboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 O3'
_chemical_formula_sum            'C27 H24 O3'
_chemical_formula_weight         396.46
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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           triclinic
_symmetry_space_group_name_H-M   'P -1  '
_symmetry_space_group_name_Hall  '-P 1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7885(4)
_cell_length_b                   10.4613(8)
_cell_length_c                   16.3808(12)
_cell_angle_alpha                92.2160(10)
_cell_angle_beta                 97.6070(10)
_cell_angle_gamma                92.5310(10)
_cell_volume                     981.26(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11621
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4505
_reflns_number_gt                3883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_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)+(0.0641P)²+0.3713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4505
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5861(2) -0.04926(11) 0.74986(7) 0.0124(2) Uani 1 1 d . . .
C2 C 0.40599(19) -0.02594(11) 0.68872(7) 0.0121(2) Uani 1 1 d . . .
C3 C 0.4386(2) 0.06800(10) 0.62848(7) 0.0114(2) Uani 1 1 d . . .
C4 C 0.2672(2) 0.07260(11) 0.55895(7) 0.0135(2) Uani 1 1 d . . .
H4 H 0.1226 0.0254 0.5575 0.016 Uiso 1 1 calc R . .
C5 C 0.3074(2) 0.14465(11) 0.49333(7) 0.0142(2) Uani 1 1 d . . .
H5 H 0.1912 0.1484 0.4469 0.017 Uiso 1 1 calc R . .
C6 C 0.5228(2) 0.21247(11) 0.49614(7) 0.0135(2) Uani 1 1 d . . .
H6 H 0.5552 0.2588 0.4499 0.016 Uiso 1 1 calc R . .
C7 C 0.6886(2) 0.21314(11) 0.56505(7) 0.0121(2) Uani 1 1 d . . .
H7 H 0.8321 0.2610 0.5655 0.015 Uiso 1 1 calc R . .
C8 C 0.64943(19) 0.14395(10) 0.63513(7) 0.0107(2) Uani 1 1 d . . .
C9 C 0.81586(19) 0.14229(10) 0.71106(7) 0.0105(2) Uani 1 1 d . . .
C10 C 0.78994(19) 0.04011(10) 0.76500(7) 0.0115(2) Uani 1 1 d . . .
C11 C 0.9542(2) 0.03405(11) 0.83572(7) 0.0133(2) Uani 1 1 d . . .
H11 H 0.9389 -0.0347 0.8712 0.016 Uiso 1 1 calc R . .
C12 C 1.1373(2) 0.12377(11) 0.85603(7) 0.0131(2) Uani 1 1 d . . .
C13 C 1.2990(2) 0.10871(12) 0.93559(8) 0.0188(3) Uani 1 1 d . . .
H13A H 1.3503 0.0197 0.9367 0.023 Uiso 1 1 calc R . .
H13B H 1.2104 0.1224 0.9826 0.023 Uiso 1 1 calc R . .
C14 C 1.5145(2) 0.20041(12) 0.94729(8) 0.0170(3) Uani 1 1 d . . .
H14A H 1.5859 0.2040 1.0057 0.020 Uiso 1 1 calc R . .
H14B H 1.6311 0.1693 0.9131 0.020 Uiso 1 1 calc R . .
C15 C 1.4450(2) 0.33369(11) 0.92220(7) 0.0166(3) Uani 1 1 d . . .
H15A H 1.5820 0.3948 0.9342 0.020 Uiso 1 1 calc R . .
H15B H 1.3227 0.3629 0.9545 0.020 Uiso 1 1 calc R . .
C16 C 1.3536(2) 0.33083(11) 0.83035(7) 0.0151(2) Uani 1 1 d . . .
H16A H 1.2945 0.4156 0.8161 0.018 Uiso 1 1 calc R . .
H16B H 1.4839 0.3148 0.7984 0.018 Uiso 1 1 calc R . .
C17 C 1.1591(2) 0.22838(11) 0.80580(7) 0.0118(2) Uani 1 1 d . . .
C18 C 0.99854(19) 0.23802(10) 0.73434(7) 0.0110(2) Uani 1 1 d . . .
C19 C 1.01596(19) 0.35891(11) 0.68846(7) 0.0112(2) Uani 1 1 d . . .
C20 C 1.2019(2) 0.38508(11) 0.64420(7) 0.0127(2) Uani 1 1 d . . .
H20 H 1.3199 0.3251 0.6424 0.015 Uiso 1 1 calc R . .
C21 C 1.2157(2) 0.49808(11) 0.60280(7) 0.0153(2) Uani 1 1 d . . .
H21 H 1.3410 0.5139 0.5719 0.018 Uiso 1 1 calc R . .
C22 C 1.0477(2) 0.58800(11) 0.60637(8) 0.0167(3) Uani 1 1 d . . .
H22 H 1.0580 0.6654 0.5783 0.020 Uiso 1 1 calc R . .
C23 C 0.8639(2) 0.56405(11) 0.65139(7) 0.0160(2) Uani 1 1 d . . .
H23 H 0.7494 0.6257 0.6546 0.019 Uiso 1 1 calc R . .
C24 C 0.8477(2) 0.44998(11) 0.69164(7) 0.0134(2) Uani 1 1 d . . .
H24 H 0.7207 0.4338 0.7217 0.016 Uiso 1 1 calc R . .
C25 C 0.5559(2) -0.16799(11) 0.79393(7) 0.0141(2) Uani 1 1 d . . .
C26 C 0.7247(2) -0.34351(11) 0.86188(7) 0.0159(2) Uani 1 1 d . . .
H26A H 0.6543 -0.4071 0.8183 0.019 Uiso 1 1 calc R . .
H26B H 0.6217 -0.3391 0.9055 0.019 Uiso 1 1 calc R . .
C27 C 0.9645(2) -0.38116(13) 0.89740(9) 0.0243(3) Uani 1 1 d . . .
H27A H 1.0688 -0.3766 0.8550 0.036 Uiso 1 1 calc R . .
H27B H 0.9550 -0.4688 0.9161 0.036 Uiso 1 1 calc R . .
H27C H 1.0254 -0.3225 0.9442 0.036 Uiso 1 1 calc R . .
O1 O 0.20161(14) -0.09438(8) 0.67560(5) 0.01613(19) Uani 1 1 d . . .
O2 O 0.36503(15) -0.22315(9) 0.79635(6) 0.0223(2) Uani 1 1 d . . .
O3 O 0.75310(14) -0.21830(8) 0.82747(5) 0.01524(19) Uani 1 1 d . . .
H1O H 0.202(3) -0.1464(15) 0.7171(10) 0.018 Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3835(16) . ?
C1 C10 1.4613(15) . ?
C1 C25 1.4757(15) . ?
C2 O1 1.3433(14) . ?
C2 C3 1.4433(16) . ?
C3 C4 1.4118(16) . ?
C3 C8 1.4158(15) . ?
C4 C5 1.3753(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4012(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3811(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4183(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4701(15) . ?
C9 C18 1.4272(15) . ?
C9 C10 1.4283(15) . ?
C10 C11 1.4033(16) . ?
C11 C12 1.3818(16) . ?
C11 H11 0.9500 . ?
C12 C17 1.4056(16) . ?
C12 C13 1.5184(16) . ?
C13 C14 1.5264(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5246(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5262(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5223(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.4050(16) . ?
C18 C19 1.5022(15) . ?
C19 C24 1.3965(16) . ?
C19 C20 1.3983(16) . ?
C20 C21 1.3899(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3879(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3915(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3910(16) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O2 1.2300(15) . ?
C25 O3 1.3382(14) . ?
C26 O3 1.4571(13) . ?
C26 C27 1.5071(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O1 H1O 0.887(16) . ?

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 C10 119.50(10) . . ?
C2 C1 C25 115.47(10) . . ?
C10 C1 C25 125.01(10) . . ?
O1 C2 C1 124.08(10) . . ?
O1 C2 C3 115.22(10) . . ?
C1 C2 C3 120.40(10) . . ?
C4 C3 C8 121.06(10) . . ?
C4 C3 C2 118.43(10) . . ?
C8 C3 C2 120.18(10) . . ?
C5 C4 C3 120.70(11) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.88(11) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.11(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.49(11) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C3 C8 C7 116.44(10) . . ?
C3 C8 C9 119.07(10) . . ?
C7 C8 C9 124.44(10) . . ?
C18 C9 C10 118.42(10) . . ?
C18 C9 C8 123.67(10) . . ?
C10 C9 C8 117.90(10) . . ?
C11 C10 C9 118.46(10) . . ?
C11 C10 C1 121.15(10) . . ?
C9 C10 C1 120.21(10) . . ?
C12 C11 C10 122.84(10) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C17 119.51(10) . . ?
C11 C12 C13 117.75(10) . . ?
C17 C12 C13 122.62(10) . . ?
C12 C13 C14 114.18(10) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 109.59(10) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C16 109.93(10) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 112.56(9) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C12 119.46(10) . . ?
C18 C17 C16 120.92(10) . . ?
C12 C17 C16 119.60(10) . . ?
C17 C18 C9 121.16(10) . . ?
C17 C18 C19 116.70(10) . . ?
C9 C18 C19 121.92(10) . . ?
C24 C19 C20 118.56(10) . . ?
C24 C19 C18 119.88(10) . . ?
C20 C19 C18 121.53(10) . . ?
C21 C20 C19 120.58(11) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.40(11) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.55(11) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.09(11) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.80(11) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O2 C25 O3 120.88(10) . . ?
O2 C25 C1 123.34(11) . . ?
O3 C25 C1 115.64(10) . . ?
O3 C26 C27 106.96(10) . . ?
O3 C26 H26A 110.3 . . ?
C27 C26 H26A 110.3 . . ?
O3 C26 H26B 110.3 . . ?
C27 C26 H26B 110.3 . . ?
H26A C26 H26B 108.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 O1 H1O 106.2(10) . . ?
C25 O3 C26 115.52(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
C10 C1 C2 O1 -172.83(10) . . . . ?
C25 C1 C2 O1 8.67(16) . . . . ?
C10 C1 C2 C3 13.76(17) . . . . ?
C25 C1 C2 C3 -164.74(10) . . . . ?
O1 C2 C3 C4 -5.25(15) . . . . ?
C1 C2 C3 C4 168.73(10) . . . . ?
O1 C2 C3 C8 -178.74(10) . . . . ?
C1 C2 C3 C8 -4.76(17) . . . . ?
C8 C3 C4 C5 4.39(17) . . . . ?
C2 C3 C4 C5 -169.04(11) . . . . ?
C3 C4 C5 C6 0.71(17) . . . . ?
C4 C5 C6 C7 -3.36(17) . . . . ?
C5 C6 C7 C8 0.94(17) . . . . ?
C4 C3 C8 C7 -6.56(16) . . . . ?
C2 C3 C8 C7 166.75(10) . . . . ?
C4 C3 C8 C9 176.01(10) . . . . ?
C2 C3 C8 C9 -10.67(16) . . . . ?
C6 C7 C8 C3 3.95(16) . . . . ?
C6 C7 C8 C9 -178.77(10) . . . . ?
C3 C8 C9 C18 -162.20(10) . . . . ?
C7 C8 C9 C18 20.59(17) . . . . ?
C3 C8 C9 C10 16.68(15) . . . . ?
C7 C8 C9 C10 -160.52(11) . . . . ?
C18 C9 C10 C11 -4.01(16) . . . . ?
C8 C9 C10 C11 177.04(10) . . . . ?
C18 C9 C10 C1 171.07(10) . . . . ?
C8 C9 C10 C1 -7.87(15) . . . . ?
C2 C1 C10 C11 167.68(11) . . . . ?
C25 C1 C10 C11 -13.98(17) . . . . ?
C2 C1 C10 C9 -7.27(16) . . . . ?
C25 C1 C10 C9 171.07(11) . . . . ?
C9 C10 C11 C12 1.11(17) . . . . ?
C1 C10 C11 C12 -173.93(11) . . . . ?
C10 C11 C12 C17 1.92(18) . . . . ?
C10 C11 C12 C13 178.20(11) . . . . ?
C11 C12 C13 C14 171.98(11) . . . . ?
C17 C12 C13 C14 -11.86(17) . . . . ?
C12 C13 C14 C15 42.69(14) . . . . ?
C13 C14 C15 C16 -64.08(13) . . . . ?
C14 C15 C16 C17 53.17(14) . . . . ?
C11 C12 C17 C18 -1.92(17) . . . . ?
C13 C12 C17 C18 -178.01(11) . . . . ?
C11 C12 C17 C16 176.97(11) . . . . ?
C13 C12 C17 C16 0.88(17) . . . . ?
C15 C16 C17 C18 157.21(11) . . . . ?
C15 C16 C17 C12 -21.66(15) . . . . ?
C12 C17 C18 C9 -1.09(17) . . . . ?
C16 C17 C18 C9 -179.97(10) . . . . ?
C12 C17 C18 C19 173.61(10) . . . . ?
C16 C17 C18 C19 -5.27(16) . . . . ?
C10 C9 C18 C17 4.06(16) . . . . ?
C8 C9 C18 C17 -177.06(10) . . . . ?
C10 C9 C18 C19 -170.35(10) . . . . ?
C8 C9 C18 C19 8.52(17) . . . . ?
C17 C18 C19 C24 -106.95(12) . . . . ?
C9 C18 C19 C24 67.70(15) . . . . ?
C17 C18 C19 C20 71.01(14) . . . . ?
C9 C18 C19 C20 -114.34(13) . . . . ?
C24 C19 C20 C21 -1.43(17) . . . . ?
C18 C19 C20 C21 -179.41(10) . . . . ?
C19 C20 C21 C22 1.48(17) . . . . ?
C20 C21 C22 C23 -0.35(18) . . . . ?
C21 C22 C23 C24 -0.79(18) . . . . ?
C22 C23 C24 C19 0.82(17) . . . . ?
C20 C19 C24 C23 0.28(17) . . . . ?
C18 C19 C24 C23 178.30(10) . . . . ?
C2 C1 C25 O2 -21.40(17) . . . . ?
C10 C1 C25 O2 160.20(12) . . . . ?
C2 C1 C25 O3 154.38(11) . . . . ?
C10 C1 C25 O3 -24.03(16) . . . . ?
O2 C25 O3 C26 3.27(16) . . . . ?
C1 C25 O3 C26 -172.62(10) . . . . ?
C27 C26 O3 C25 -179.01(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

