data_2006sot0997

_chemical_compound_source            'Huma Aslam Bhatti'

loop_
_publ_author_name
'Mark Light'
'Huma Aslam Bhatti'
'Jeremy Kilbrun'

_journal_coden_Cambridge    1078
_journal_year                        2006
_journal_name_full                'Private Communication '
_database_code_CSD                6SOT0997
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C23 H18 O4'
_chemical_formula_weight          358.37
 
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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c 
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                    10.4036(3)
_cell_length_b                    20.8256(6)
_cell_length_c                    8.1261(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  100.103(2)
_cell_angle_gamma                 90.00
_cell_volume                      1733.31(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4086
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'Fragment'
_exptl_crystal_colour             'Colourless'
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.373
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              752
_exptl_absorpt_coefficient_mu     0.094
 _exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min   0.9625
_exptl_absorpt_correction_T_max   0.9972
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
 
_exptl_special_details
;
SADABS was used to perform the Absorption correction
Parameter refinement on 14191 reflections reduced R(int) from 0.0750 to 0.0392
Ratio of minimum to maximum apparent transmission:  0.801778
The given Tmin and Tmax were generated using the SHELX SIZE command
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  'graphite'
_diffrn_measurement_device_type   'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method        '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number   0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             24806
_diffrn_reflns_av_R_equivalents   0.0571
_diffrn_reflns_av_sigmaI/netI     0.0477
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -27
_diffrn_reflns_limit_k_max        26
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3973
_reflns_number_gt                 2636
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution   'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)' 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0984P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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          3973
_refine_ls_number_parameters      245
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0865
_refine_ls_R_factor_gt            0.0477
_refine_ls_wR_factor_ref          0.1462
_refine_ls_wR_factor_gt           0.1220
_refine_ls_goodness_of_fit_ref    0.958
_refine_ls_restrained_S_all       0.958
_refine_ls_shift/su_max           0.001
_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 0.71722(16) 0.65602(8) 0.96656(19) 0.0232(4) Uani 1 1 d . . .
C2 C 0.82336(15) 0.66623(8) 1.10999(19) 0.0219(4) Uani 1 1 d . . .
C3 C 0.79571(17) 0.68324(8) 1.2668(2) 0.0256(4) Uani 1 1 d . . .
H3 H 0.7076 0.6876 1.2820 0.031 Uiso 1 1 calc R . .
C4 C 0.89588(17) 0.69374(8) 1.3990(2) 0.0280(4) Uani 1 1 d . . .
H4 H 0.8770 0.7059 1.5048 0.034 Uiso 1 1 calc R . .
C5 C 1.02523(17) 0.68649(8) 1.3774(2) 0.0301(4) Uani 1 1 d . . .
H5 H 1.0937 0.6938 1.4694 0.036 Uiso 1 1 calc R . .
C6 C 1.05571(17) 0.66897(8) 1.2253(2) 0.0295(4) Uani 1 1 d . . .
H6 H 1.1438 0.6633 1.2116 0.035 Uiso 1 1 calc R . .
C7 C 0.95313(16) 0.65978(8) 1.0922(2) 0.0242(4) Uani 1 1 d . . .
C9 C 0.88976(16) 0.63587(8) 0.8081(2) 0.0266(4) Uani 1 1 d . . .
H9 H 0.9150 0.6257 0.7043 0.032 Uiso 1 1 calc R . .
C10 C 0.76064(16) 0.64097(8) 0.8090(2) 0.0228(4) Uani 1 1 d . . .
C11 C 0.66408(16) 0.62892(8) 0.65407(19) 0.0229(4) Uani 1 1 d . . .
C12 C 0.67518(16) 0.57608(8) 0.55390(19) 0.0263(4) Uani 1 1 d . . .
H12 H 0.7456 0.5470 0.5847 0.032 Uiso 1 1 calc R . .
C13 C 0.58476(17) 0.56499(8) 0.4088(2) 0.0262(4) Uani 1 1 d . . .
H13 H 0.5943 0.5286 0.3414 0.031 Uiso 1 1 calc R . .
C14 C 0.48119(15) 0.60652(8) 0.36231(19) 0.0225(4) Uani 1 1 d . . .
C15 C 0.46833(15) 0.66064(8) 0.46288(19) 0.0211(4) Uani 1 1 d . . .
C16 C 0.55942(15) 0.67145(8) 0.60644(19) 0.0221(4) Uani 1 1 d . . .
H16 H 0.5509 0.7081 0.6734 0.027 Uiso 1 1 calc R . .
C17 C 0.40743(17) 0.54723(8) 0.11375(19) 0.0261(4) Uani 1 1 d . . .
H17A H 0.4032 0.5057 0.1719 0.031 Uiso 1 1 calc R . .
H17B H 0.4953 0.5513 0.0839 0.031 Uiso 1 1 calc R . .
C18 C 0.30562(15) 0.54879(8) -0.04204(19) 0.0233(4) Uani 1 1 d . . .
C19 C 0.32692(16) 0.58452(8) -0.17931(19) 0.0246(4) Uani 1 1 d . . .
H19 H 0.4033 0.6102 -0.1714 0.030 Uiso 1 1 calc R . .
C20 C 0.23772(16) 0.58305(8) -0.3276(2) 0.0262(4) Uani 1 1 d . . .
H20 H 0.2526 0.6081 -0.4201 0.031 Uiso 1 1 calc R . .
C21 C 0.12718(17) 0.54516(8) -0.3412(2) 0.0277(4) Uani 1 1 d . . .
H21 H 0.0667 0.5438 -0.4434 0.033 Uiso 1 1 calc R . .
C22 C 0.10480(17) 0.50927(9) -0.2058(2) 0.0314(4) Uani 1 1 d . . .
H22 H 0.0287 0.4833 -0.2147 0.038 Uiso 1 1 calc R . .
C23 C 0.19371(16) 0.51117(8) -0.0567(2) 0.0287(4) Uani 1 1 d . . .
H23 H 0.1779 0.4865 0.0361 0.034 Uiso 1 1 calc R . .
C24 C 0.34465(16) 0.75310(8) 0.5115(2) 0.0258(4) Uani 1 1 d . . .
H24A H 0.3315 0.7384 0.6219 0.039 Uiso 1 1 calc R . .
H24B H 0.2682 0.7777 0.4585 0.039 Uiso 1 1 calc R . .
H24C H 0.4224 0.7804 0.5238 0.039 Uiso 1 1 calc R . .
O3 O 0.38578(11) 0.59923(5) 0.22310(13) 0.0256(3) Uani 1 1 d . . .
O4 O 0.98679(11) 0.64388(6) 0.94101(14) 0.0301(3) Uani 1 1 d . . .
O1 O 0.60190(11) 0.65925(6) 0.98022(14) 0.0328(3) Uani 1 1 d . . .
O2 O 0.36194(10) 0.69857(5) 0.40925(13) 0.0235(3) Uani 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0202(9) 0.0237(9) 0.0246(9) 0.0021(7) 0.0007(7) 0.0010(7)
C2 0.0228(9) 0.0209(9) 0.0208(8) 0.0021(7) 0.0007(7) -0.0004(7)
C3 0.0254(9) 0.0252(9) 0.0250(9) 0.0012(7) 0.0014(7) 0.0001(7)
C4 0.0353(10) 0.0238(9) 0.0227(8) 0.0014(7) -0.0012(7) -0.0018(8)
C5 0.0307(10) 0.0290(10) 0.0262(9) 0.0040(7) -0.0067(7) -0.0045(8)
C6 0.0223(9) 0.0318(10) 0.0316(10) 0.0071(8) -0.0033(7) -0.0005(8)
C7 0.0232(9) 0.0256(9) 0.0227(9) 0.0043(7) 0.0006(7) 0.0008(7)
C9 0.0262(9) 0.0329(10) 0.0196(8) 0.0045(7) 0.0013(7) 0.0047(8)
C10 0.0236(9) 0.0225(8) 0.0214(8) 0.0023(7) 0.0010(7) 0.0017(7)
C11 0.0228(9) 0.0261(9) 0.0191(8) 0.0020(7) 0.0018(6) -0.0009(7)
C12 0.0249(9) 0.0289(9) 0.0236(8) 0.0018(7) 0.0001(7) 0.0060(7)
C13 0.0302(9) 0.0255(9) 0.0224(8) -0.0032(7) 0.0033(7) 0.0032(8)
C14 0.0234(9) 0.0251(9) 0.0184(8) -0.0003(7) 0.0018(7) -0.0005(7)
C15 0.0214(8) 0.0226(9) 0.0198(8) 0.0040(7) 0.0047(7) 0.0019(7)
C16 0.0230(9) 0.0239(9) 0.0191(8) -0.0005(7) 0.0027(7) 0.0013(7)
C17 0.0310(10) 0.0242(9) 0.0216(9) -0.0038(7) 0.0005(7) 0.0046(7)
C18 0.0260(9) 0.0216(8) 0.0215(8) -0.0046(7) 0.0023(7) 0.0050(7)
C19 0.0237(9) 0.0229(9) 0.0262(9) -0.0026(7) 0.0016(7) -0.0018(7)
C20 0.0292(10) 0.0254(9) 0.0237(8) 0.0011(7) 0.0039(7) 0.0028(8)
C21 0.0264(9) 0.0274(9) 0.0265(9) -0.0035(7) -0.0028(7) 0.0020(7)
C22 0.0281(10) 0.0279(10) 0.0369(10) -0.0016(8) 0.0017(8) -0.0071(8)
C23 0.0329(10) 0.0259(9) 0.0271(9) 0.0025(7) 0.0049(8) -0.0016(8)
C24 0.0251(9) 0.0236(9) 0.0286(9) -0.0039(7) 0.0040(7) 0.0032(7)
O3 0.0264(6) 0.0281(6) 0.0204(6) -0.0057(5) -0.0013(5) 0.0035(5)
O4 0.0203(6) 0.0450(8) 0.0238(6) 0.0023(5) 0.0003(5) 0.0031(5)
O1 0.0200(7) 0.0513(8) 0.0263(7) -0.0056(6) 0.0014(5) 0.0001(6)
O2 0.0226(6) 0.0247(6) 0.0216(6) -0.0015(5) -0.0005(5) 0.0054(5)
 
_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 1.2260(19) . ?
C1 C10 1.465(2) . ?
C1 C2 1.474(2) . ?
C2 C7 1.389(2) . ?
C2 C3 1.400(2) . ?
C3 C4 1.377(2) . ?
C4 C5 1.395(3) . ?
C5 C6 1.378(3) . ?
C6 C7 1.393(2) . ?
C7 O4 1.3758(19) . ?
C9 C10 1.349(2) . ?
C9 O4 1.3533(19) . ?
C10 C11 1.488(2) . ?
C11 C12 1.386(2) . ?
C11 C16 1.404(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.382(2) . ?
C14 O3 1.3763(18) . ?
C14 C15 1.412(2) . ?
C15 O2 1.3675(19) . ?
C15 C16 1.386(2) . ?
C17 O3 1.4433(19) . ?
C17 C18 1.502(2) . ?
C18 C19 1.391(2) . ?
C18 C23 1.391(2) . ?
C19 C20 1.386(2) . ?
C20 C21 1.383(2) . ?
C21 C22 1.384(2) . ?
C22 C23 1.390(2) . ?
C24 O2 1.4368(19) . ?
 
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 123.22(14) . . ?
O1 C1 C2 122.00(14) . . ?
C10 C1 C2 114.78(14) . . ?
C7 C2 C3 118.53(15) . . ?
C7 C2 C1 120.72(14) . . ?
C3 C2 C1 120.74(15) . . ?
C4 C3 C2 120.13(16) . . ?
C3 C4 C5 119.98(16) . . ?
C6 C5 C4 121.33(16) . . ?
C5 C6 C7 117.86(16) . . ?
O4 C7 C2 121.36(14) . . ?
O4 C7 C6 116.48(15) . . ?
C2 C7 C6 122.16(15) . . ?
C10 C9 O4 126.16(15) . . ?
C9 C10 C1 118.82(14) . . ?
C9 C10 C11 120.49(15) . . ?
C1 C10 C11 120.65(14) . . ?
C12 C11 C16 118.66(15) . . ?
C12 C11 C10 121.17(15) . . ?
C16 C11 C10 120.17(15) . . ?
C11 C12 C13 121.03(15) . . ?
C14 C13 C12 120.42(15) . . ?
O3 C14 C13 124.83(14) . . ?
O3 C14 C15 115.84(13) . . ?
C13 C14 C15 119.33(14) . . ?
O2 C15 C16 124.74(14) . . ?
O2 C15 C14 115.48(13) . . ?
C16 C15 C14 119.77(15) . . ?
C15 C16 C11 120.79(15) . . ?
O3 C17 C18 109.86(12) . . ?
C19 C18 C23 118.78(14) . . ?
C19 C18 C17 119.98(15) . . ?
C23 C18 C17 121.06(15) . . ?
C20 C19 C18 120.59(15) . . ?
C21 C20 C19 120.18(15) . . ?
C20 C21 C22 119.87(15) . . ?
C21 C22 C23 119.93(16) . . ?
C22 C23 C18 120.64(16) . . ?
C14 O3 C17 114.89(12) . . ?
C9 O4 C7 118.13(13) . . ?
C15 O2 C24 116.67(12) . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.219
_refine_diff_density_min   -0.296
_refine_diff_density_rms    0.055