# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4c-o

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 methyl 4-benzyl-5-methoxynaphthalene-2-carboxylate 
;
_chemical_name_common            naphthalane
_chemical_melting_point          363(1)
_chemical_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34

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'

_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                   8.1761(14)
_cell_length_b                   8.3698(19)
_cell_length_c                   12.1493(14)
_cell_angle_alpha                76.098(15)
_cell_angle_beta                 80.854(12)
_cell_angle_gamma                89.732(16)
_cell_volume                     796.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1628
_cell_measurement_theta_min      3.4980
_cell_measurement_theta_max      28.2760

_exptl_crystal_description       black
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4790
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         24.70
_reflns_number_total             2712
_reflns_number_gt                1812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0846P)²+0.0000P] 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         2712
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C10 C 0.3353(2) 0.6657(2) 0.74012(15) 0.0438(5) Uani 1 1 d . . .
C2 C 0.0562(2) 0.7472(2) 0.62991(16) 0.0480(5) Uani 1 1 d . . .
O3 O 0.52054(16) 0.69548(18) 0.86664(12) 0.0614(4) Uani 1 1 d . . .
C3 C 0.1020(2) 0.8369(2) 0.70473(16) 0.0468(5) Uani 1 1 d . . .
H3 H 0.0373 0.9240 0.7184 0.056 Uiso 1 1 calc R . .
C4 C 0.2376(2) 0.8021(2) 0.75869(15) 0.0427(5) Uani 1 1 d . . .
C9 C 0.2905(2) 0.5760(2) 0.66273(16) 0.0513(5) Uani 1 1 d . . .
C5 C 0.4782(2) 0.6117(2) 0.79196(17) 0.0504(5) Uani 1 1 d . . .
O2 O -0.18324(16) 0.8991(2) 0.61155(12) 0.0656(5) Uani 1 1 d . . .
C1 C 0.1508(2) 0.6200(3) 0.60903(16) 0.0537(5) Uani 1 1 d . . .
H1 H 0.1227 0.5613 0.5584 0.064 Uiso 1 1 calc R . .
C14 C 0.2029(2) 0.8526(2) 0.96035(16) 0.0460(5) Uani 1 1 d . . .
C13 C 0.2714(2) 0.9133(2) 0.83418(17) 0.0487(5) Uani 1 1 d . . .
H13A H 0.2255 1.0197 0.8060 0.058 Uiso 1 1 calc R . .
H13B H 0.3904 0.9302 0.8261 0.058 Uiso 1 1 calc R . .
O1 O -0.12489(19) 0.7273(2) 0.49864(15) 0.0893(6) Uani 1 1 d . . .
C11 C -0.0904(2) 0.7876(3) 0.57251(17) 0.0555(5) Uani 1 1 d . . .
C6 C 0.5652(3) 0.4821(3) 0.7671(2) 0.0719(7) Uani 1 1 d . . .
H6 H 0.6577 0.4496 0.8015 0.086 Uiso 1 1 calc R . .
C15 C 0.0792(2) 0.7335(3) 1.00132(17) 0.0580(6) Uani 1 1 d . . .
H15 H 0.0393 0.6822 0.9505 0.070 Uiso 1 1 calc R . .
C19 C 0.2599(3) 0.9250(3) 1.0388(2) 0.0638(6) Uani 1 1 d . . .
H19 H 0.3452 1.0049 1.0136 0.077 Uiso 1 1 calc R . .
C8 C 0.3832(3) 0.4414(3) 0.6405(2) 0.0721(7) Uani 1 1 d . . .
H8 H 0.3515 0.3826 0.5909 0.086 Uiso 1 1 calc R . .
C20 C 0.6661(2) 0.6504(3) 0.9150(2) 0.0718(7) Uani 1 1 d . . .
H20A H 0.6581 0.5353 0.9529 0.108 Uiso 1 1 calc R . .
H20B H 0.6777 0.7138 0.9697 0.108 Uiso 1 1 calc R . .
H20C H 0.7609 0.6715 0.8552 0.108 Uiso 1 1 calc R . .
C18 C 0.1924(3) 0.8807(3) 1.1538(2) 0.0750(8) Uani 1 1 d . . .
H18 H 0.2315 0.9317 1.2050 0.090 Uiso 1 1 calc R . .
C12 C -0.3329(2) 0.9414(3) 0.56420(19) 0.0733(7) Uani 1 1 d . . .
H12A H -0.3053 0.9870 0.4829 0.110 Uiso 1 1 calc R . .
H12B H -0.3902 1.0211 0.5997 0.110 Uiso 1 1 calc R . .
H12C H -0.4028 0.8444 0.5785 0.110 Uiso 1 1 calc R . .
C17 C 0.0691(3) 0.7631(3) 1.1925(2) 0.0754(7) Uani 1 1 d . . .
H17 H 0.0233 0.7337 1.2700 0.091 Uiso 1 1 calc R . .
C7 C 0.5179(3) 0.3976(3) 0.6908(2) 0.0876(9) Uani 1 1 d . . .
H7 H 0.5796 0.3101 0.6745 0.105 Uiso 1 1 calc R . .
C16 C 0.0126(3) 0.6879(3) 1.11667(19) 0.0731(7) Uani 1 1 d . . .
H16 H -0.0708 0.6062 1.1428 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C10 C9 1.426(2) . ?
C10 C4 1.432(2) . ?
C10 C5 1.435(2) . ?
C2 C1 1.362(3) . ?
C2 C3 1.403(2) . ?
C2 C11 1.479(3) . ?
O3 C5 1.357(2) . ?
O3 C20 1.420(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 C13 1.509(2) . ?
C9 C1 1.408(2) . ?
C9 C8 1.410(3) . ?
C5 C6 1.363(3) . ?
O2 C11 1.328(2) . ?
O2 C12 1.440(2) . ?
C1 H1 0.9300 . ?
C14 C15 1.370(3) . ?
C14 C19 1.383(3) . ?
C14 C13 1.509(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O1 C11 1.199(2) . ?
C6 C7 1.393(3) . ?
C6 H6 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C19 C18 1.379(3) . ?
C19 H19 0.9300 . ?
C8 C7 1.351(3) . ?
C8 H8 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 C17 1.357(3) . ?
C18 H18 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C10 C4 118.33(16) . . ?
C9 C10 C5 116.31(16) . . ?
C4 C10 C5 125.35(17) . . ?
C1 C2 C3 118.80(17) . . ?
C1 C2 C11 119.22(18) . . ?
C3 C2 C11 121.98(17) . . ?
C5 O3 C20 118.00(15) . . ?
C4 C3 C2 123.06(17) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 C10 118.68(17) . . ?
C3 C4 C13 116.20(15) . . ?
C10 C4 C13 125.13(15) . . ?
C1 C9 C8 119.37(18) . . ?
C1 C9 C10 119.89(17) . . ?
C8 C9 C10 120.73(17) . . ?
O3 C5 C6 122.34(17) . . ?
O3 C5 C10 116.64(16) . . ?
C6 C5 C10 121.02(19) . . ?
C11 O2 C12 116.97(17) . . ?
C2 C1 C9 121.21(18) . . ?
C2 C1 H1 119.4 . . ?
C9 C1 H1 119.4 . . ?
C15 C14 C19 117.63(19) . . ?
C15 C14 C13 122.88(17) . . ?
C19 C14 C13 119.40(19) . . ?
C4 C13 C14 115.82(16) . . ?
C4 C13 H13A 108.3 . . ?
C14 C13 H13A 108.3 . . ?
C4 C13 H13B 108.3 . . ?
C14 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
O1 C11 O2 122.42(18) . . ?
O1 C11 C2 124.7(2) . . ?
O2 C11 C2 112.89(17) . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C18 C19 C14 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.70
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 982203'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5r

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 methyl 1-phenylphenanthrene-3-carboxylate
;
_chemical_name_common            phenanthrene
_chemical_melting_point          406(1)
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   11.092(4)
_cell_length_b                   17.545(6)
_cell_length_c                   17.517(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.638(18)
_cell_angle_gamma                90.00
_cell_volume                     3190.2(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8313
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.74

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_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            31762
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.20
_reflns_number_total             6356
_reflns_number_gt                4491
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 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)+(0.0725P)²+0.1215P] 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         6356
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.011
_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
O1 O -0.07468(11) 0.36118(6) 0.19540(8) 0.0707(3) Uani 1 1 d . . .
O2 O 0.00348(10) 0.24550(6) 0.18913(7) 0.0634(3) Uani 1 1 d . . .
C1 C 0.22038(13) 0.45627(8) 0.12637(8) 0.0487(3) Uani 1 1 d . . .
C2 C 0.12595(13) 0.42756(8) 0.15187(8) 0.0503(3) Uani 1 1 d . . .
H2 H 0.0699 0.4609 0.1639 0.060 Uiso 1 1 calc R . .
C3 C 0.11249(13) 0.34910(8) 0.16009(8) 0.0464(3) Uani 1 1 d . . .
C4 C 0.19667(13) 0.29993(8) 0.14418(8) 0.0472(3) Uani 1 1 d . . .
H4 H 0.1879 0.2478 0.1505 0.057 Uiso 1 1 calc R . .
C5 C 0.38347(14) 0.19517(8) 0.11431(9) 0.0576(4) Uani 1 1 d . . .
H5 H 0.3235 0.1745 0.1345 0.069 Uiso 1 1 calc R . .
C6 C 0.46825(15) 0.14798(9) 0.09703(10) 0.0658(4) Uani 1 1 d . . .
H6 H 0.4659 0.0958 0.1060 0.079 Uiso 1 1 calc R . .
C7 C 0.55784(16) 0.17725(11) 0.06627(11) 0.0708(5) Uani 1 1 d . . .
H7 H 0.6148 0.1447 0.0541 0.085 Uiso 1 1 calc R . .
C8 C 0.56250(15) 0.25318(11) 0.05401(10) 0.0671(4) Uani 1 1 d . . .
H8 H 0.6228 0.2723 0.0332 0.080 Uiso 1 1 calc R . .
C9 C 0.48403(15) 0.38361(9) 0.06127(10) 0.0617(4) Uani 1 1 d . . .
H9 H 0.5451 0.4029 0.0412 0.074 Uiso 1 1 calc R . .
C10 C 0.40388(14) 0.43223(9) 0.07918(9) 0.0567(4) Uani 1 1 d . . .
H10 H 0.4121 0.4843 0.0724 0.068 Uiso 1 1 calc R . .
C11 C 0.30661(13) 0.40535(8) 0.10829(8) 0.0467(3) Uani 1 1 d . . .
C12 C 0.29531(12) 0.32613(8) 0.11879(8) 0.0450(3) Uani 1 1 d . . .
C13 C 0.38500(13) 0.27426(8) 0.10222(8) 0.0478(3) Uani 1 1 d . . .
C14 C 0.47799(13) 0.30355(9) 0.07214(9) 0.0530(4) Uani 1 1 d . . .
C15 C 0.23141(13) 0.54014(8) 0.11710(9) 0.0490(3) Uani 1 1 d . . .
C16 C 0.17460(16) 0.57539(9) 0.04300(10) 0.0666(4) Uani 1 1 d . . .
H16 H 0.1277 0.5465 -0.0023 0.080 Uiso 1 1 calc R . .
C17 C 0.18608(17) 0.65289(9) 0.03483(10) 0.0702(5) Uani 1 1 d . . .
H17 H 0.1470 0.6757 -0.0158 0.084 Uiso 1 1 calc R . .
C18 C 0.25389(15) 0.69622(9) 0.10011(10) 0.0599(4) Uani 1 1 d . . .
H18 H 0.2618 0.7485 0.0943 0.072 Uiso 1 1 calc R . .
C19 C 0.31017(16) 0.66229(9) 0.17416(10) 0.0652(4) Uani 1 1 d . . .
H19 H 0.3561 0.6916 0.2193 0.078 Uiso 1 1 calc R . .
C20 C 0.29950(16) 0.58505(9) 0.18252(10) 0.0659(4) Uani 1 1 d . . .
H20 H 0.3390 0.5626 0.2334 0.079 Uiso 1 1 calc R . .
C21 C 0.00476(13) 0.32103(8) 0.18371(8) 0.0495(3) Uani 1 1 d . . .
C22 C -0.09965(15) 0.21212(9) 0.20935(11) 0.0690(5) Uani 1 1 d . . .
H22A H -0.1807 0.2271 0.1696 0.104 Uiso 1 1 calc R . .
H22B H -0.0950 0.2294 0.2623 0.104 Uiso 1 1 calc R . .
H22C H -0.0922 0.1576 0.2097 0.104 Uiso 1 1 calc R . .
O3 O 0.56310(11) 0.47900(6) 0.31051(7) 0.0679(3) Uani 1 1 d . . .
O4 O 0.60787(10) 0.35696(5) 0.30033(7) 0.0610(3) Uani 1 1 d . . .
C23 C 0.25663(13) 0.41491(7) 0.38664(8) 0.0453(3) Uani 1 1 d . . .
C24 C 0.35860(13) 0.43757(8) 0.36477(8) 0.0465(3) Uani 1 1 d . . .
H24 H 0.3781 0.4892 0.3655 0.056 Uiso 1 1 calc R . .
C25 C 0.43366(12) 0.38476(7) 0.34149(8) 0.0437(3) Uani 1 1 d . . .
C26 C 0.40561(13) 0.30869(8) 0.34086(8) 0.0447(3) Uani 1 1 d . . .
H26 H 0.4552 0.2737 0.3250 0.054 Uiso 1 1 calc R . .
C27 C 0.33950(15) 0.14569(8) 0.33541(9) 0.0576(4) Uani 1 1 d . . .
H27 H 0.4068 0.1600 0.3184 0.069 Uiso 1 1 calc R . .
C28 C 0.30703(16) 0.07062(9) 0.33351(10) 0.0675(4) Uani 1 1 d . . .
H28 H 0.3517 0.0346 0.3149 0.081 Uiso 1 1 calc R . .
C29 C 0.20758(17) 0.04749(9) 0.35925(11) 0.0697(5) Uani 1 1 d . . .
H29 H 0.1857 -0.0038 0.3578 0.084 Uiso 1 1 calc R . .
C30 C 0.14277(16) 0.10020(9) 0.38644(10) 0.0642(4) Uani 1 1 d . . .
H30 H 0.0768 0.0845 0.4040 0.077 Uiso 1 1 calc R . .
C31 C 0.10435(14) 0.23394(9) 0.41531(9) 0.0572(4) Uani 1 1 d . . .
H31 H 0.0401 0.2181 0.4344 0.069 Uiso 1 1 calc R . .
C32 C 0.12879(13) 0.30874(8) 0.41381(8) 0.0527(4) Uani 1 1 d . . .
H32 H 0.0796 0.3435 0.4303 0.063 Uiso 1 1 calc R . .
C33 C 0.22893(12) 0.33596(8) 0.38738(7) 0.0443(3) Uani 1 1 d . . .
C34 C 0.30421(12) 0.28256(7) 0.36354(8) 0.0427(3) Uani 1 1 d . . .
C35 C 0.27393(13) 0.20174(8) 0.36233(8) 0.0464(3) Uani 1 1 d . . .
C36 C 0.17338(14) 0.17826(8) 0.38869(8) 0.0508(3) Uani 1 1 d . . .
C37 C 0.17708(14) 0.47433(8) 0.40753(8) 0.0480(3) Uani 1 1 d . . .
C38 C 0.22973(16) 0.52047(9) 0.47458(9) 0.0627(4) Uani 1 1 d . . .
H38 H 0.3145 0.5130 0.5089 0.075 Uiso 1 1 calc R . .
C39 C 0.1574(2) 0.57790(10) 0.49116(11) 0.0754(5) Uani 1 1 d . . .
H39 H 0.1939 0.6086 0.5368 0.090 Uiso 1 1 calc R . .
C40 C 0.03321(19) 0.59018(10) 0.44149(11) 0.0731(5) Uani 1 1 d . . .
H40 H -0.0147 0.6292 0.4528 0.088 Uiso 1 1 calc R . .
C41 C -0.02024(17) 0.54449(10) 0.37488(11) 0.0746(5) Uani 1 1 d . . .
H41 H -0.1051 0.5523 0.3408 0.090 Uiso 1 1 calc R . .
C42 C 0.05077(15) 0.48713(9) 0.35799(10) 0.0640(4) Uani 1 1 d . . .
H42 H 0.0133 0.4564 0.3125 0.077 Uiso 1 1 calc R . .
C43 C 0.53968(13) 0.41299(8) 0.31601(8) 0.0462(3) Uani 1 1 d . . .
C44 C 0.71225(15) 0.37776(9) 0.27392(11) 0.0678(5) Uani 1 1 d . . .
H44A H 0.7636 0.4165 0.3093 0.102 Uiso 1 1 calc R . .
H44B H 0.6782 0.3969 0.2191 0.102 Uiso 1 1 calc R . .
H44C H 0.7647 0.3338 0.2756 0.102 Uiso 1 1 calc R . .


_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 C21 1.2008(17) . ?
O2 C21 1.3290(18) . ?
O2 C22 1.4361(18) . ?
C1 C2 1.371(2) . ?
C1 C11 1.4237(19) . ?
C1 C15 1.4903(19) . ?
C2 C3 1.398(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.3700(19) . ?
C3 C21 1.480(2) . ?
C4 C12 1.3962(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(2) . ?
C5 C13 1.405(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.353(3) . ?
C7 H7 0.9300 . ?
C8 C14 1.404(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.346(2) . ?
C9 C14 1.422(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.426(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.413(2) . ?
C12 C13 1.4510(19) . ?
C13 C14 1.410(2) . ?
C15 C16 1.374(2) . ?
C15 C20 1.376(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.362(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O3 C43 1.1981(16) . ?
O4 C43 1.3268(16) . ?
O4 C44 1.4372(18) . ?
C23 C24 1.3746(19) . ?
C23 C33 1.4198(19) . ?
C23 C37 1.4923(19) . ?
C24 C25 1.3990(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.3697(18) . ?
C25 C43 1.4824(19) . ?
C26 C34 1.3957(19) . ?
C26 H26 0.9300 . ?
C27 C28 1.363(2) . ?
C27 C35 1.400(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.391(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.357(2) . ?
C29 H29 0.9300 . ?
C30 C36 1.408(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.342(2) . ?
C31 C36 1.418(2) . ?
C31 H31 0.9300 . ?
C32 C33 1.4279(19) . ?
C32 H32 0.9300 . ?
C33 C34 1.4125(19) . ?
C34 C35 1.4556(19) . ?
C35 C36 1.411(2) . ?
C37 C38 1.376(2) . ?
C37 C42 1.382(2) . ?
C38 C39 1.381(2) . ?
C38 H38 0.9300 . ?
C39 C40 1.362(2) . ?
C39 H39 0.9300 . ?
C40 C41 1.367(2) . ?
C40 H40 0.9300 . ?
C41 C42 1.373(2) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C22 116.98(12) . . ?
C2 C1 C11 119.48(13) . . ?
C2 C1 C15 119.98(12) . . ?
C11 C1 C15 120.53(13) . . ?
C1 C2 C3 121.13(13) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.61(13) . . ?
C4 C3 C21 121.51(13) . . ?
C2 C3 C21 118.86(12) . . ?
C3 C4 C12 121.62(13) . . ?
C3 C4 H4 119.2 . . ?
C12 C4 H4 119.2 . . ?
C6 C5 C13 121.34(15) . . ?
C6 C5 H5 119.3 . . ?
C13 C5 H5 119.3 . . ?
C5 C6 C7 120.41(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.97(15) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C14 121.20(16) . . ?
C7 C8 H8 119.4 . . ?
C14 C8 H8 119.4 . . ?
C10 C9 C14 121.90(14) . . ?
C10 C9 H9 119.1 . . ?
C14 C9 H9 119.1 . . ?
C9 C10 C11 121.24(14) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C1 119.39(13) . . ?
C12 C11 C10 118.99(13) . . ?
C1 C11 C10 121.62(13) . . ?
C4 C12 C11 118.73(12) . . ?
C4 C12 C13 121.78(13) . . ?
C11 C12 C13 119.48(13) . . ?
C5 C13 C14 117.74(13) . . ?
C5 C13 C12 122.95(13) . . ?
C14 C13 C12 119.31(13) . . ?
C8 C14 C13 119.32(15) . . ?
C8 C14 C9 121.66(15) . . ?
C13 C14 C9 119.01(13) . . ?
C16 C15 C20 117.60(14) . . ?
C16 C15 C1 121.29(13) . . ?
C20 C15 C1 121.10(13) . . ?
C15 C16 C17 120.93(14) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.59(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.28(15) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.34(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.26(14) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
O1 C21 O2 123.08(14) . . ?
O1 C21 C3 124.46(14) . . ?
O2 C21 C3 112.45(12) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C43 O4 C44 117.47(11) . . ?
C24 C23 C33 119.12(12) . . ?
C24 C23 C37 118.81(12) . . ?
C33 C23 C37 122.06(12) . . ?
C23 C24 C25 121.49(13) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 119.40(13) . . ?
C26 C25 C43 121.68(12) . . ?
C24 C25 C43 118.90(12) . . ?
C25 C26 C34 121.42(13) . . ?
C25 C26 H26 119.3 . . ?
C34 C26 H26 119.3 . . ?
C28 C27 C35 121.53(15) . . ?
C28 C27 H27 119.2 . . ?
C35 C27 H27 119.2 . . ?
C27 C28 C29 120.46(16) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C30 C29 C28 119.59(15) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C36 121.36(16) . . ?
C29 C30 H30 119.3 . . ?
C36 C30 H30 119.3 . . ?
C32 C31 C36 122.09(14) . . ?
C32 C31 H31 119.0 . . ?
C36 C31 H31 119.0 . . ?
C31 C32 C33 121.26(14) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C34 C33 C23 119.47(12) . . ?
C34 C33 C32 118.85(12) . . ?
C23 C33 C32 121.66(13) . . ?
C26 C34 C33 119.07(12) . . ?
C26 C34 C35 121.38(12) . . ?
C33 C34 C35 119.54(12) . . ?
C27 C35 C36 118.00(13) . . ?
C27 C35 C34 122.99(13) . . ?
C36 C35 C34 119.00(12) . . ?
C30 C36 C35 119.05(14) . . ?
C30 C36 C31 121.78(14) . . ?
C35 C36 C31 119.16(13) . . ?
C38 C37 C42 118.16(14) . . ?
C38 C37 C23 120.71(13) . . ?
C42 C37 C23 121.06(13) . . ?
C37 C38 C39 120.36(16) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C40 C39 C38 120.84(16) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C39 C40 C41 119.29(16) . . ?
C39 C40 H40 120.4 . . ?
C41 C40 H40 120.4 . . ?
C40 C41 C42 120.31(17) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C37 121.04(15) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
O3 C43 O4 122.95(13) . . ?
O3 C43 C25 124.38(13) . . ?
O4 C43 C25 112.67(12) . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.20
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.061


_database_code_depnum_ccdc_archive 'CCDC 982204'
