# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Dhevalapally B. Ramachary'
_publ_contact_author_email       ramsc@uohyd.ernet.in
loop_
_publ_author_name
'Dhevalapally B. Ramachary'
'Rumpa Mondal'
'R. Madhavachary'

data_dbr92
_database_code_depnum_ccdc_archive 'CCDC 804553'
#TrackingRef 'dbr92.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C1.62 H1.38 O0.23'
_chemical_formula_weight         24.49
_chemical_absolute_configuration unk

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.7710(11)
_cell_length_b                   10.930(2)
_cell_length_c                   28.102(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1772.7(6)
_cell_formula_units_Z            52
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6881
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      24.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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            18381
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0337
_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       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         26.05
_reflns_number_total             3480
_reflns_number_gt                2978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0591P)^2^+0.1988P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(17)
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
C8 C 0.6673(4) 0.4905(2) 0.90175(8) 0.0524(6) Uani 1 1 d . . .
H7A H 0.5396 0.4857 0.8794 0.063 Uiso 1 1 calc R . .
H8B H 0.7027 0.4078 0.9120 0.063 Uiso 1 1 calc R . .
O2 O 0.6261(3) 0.67128(15) 0.94657(6) 0.0625(5) Uani 1 1 d . . .
O1 O 0.1437(3) 0.62253(16) 0.99428(5) 0.0601(5) Uani 1 1 d . . .
H12 H 0.0951 0.6818 1.0091 0.090 Uiso 1 1 calc R . .
C9 C 0.5906(4) 0.5633(2) 0.94422(7) 0.0462(5) Uani 1 1 d . . .
C12 C 0.2593(4) 0.4967(2) 1.06077(7) 0.0480(5) Uani 1 1 d . . .
C1 C 0.7903(4) 0.5018(2) 0.78954(8) 0.0503(6) Uani 1 1 d . . .
C11 C 0.3365(4) 0.5713(2) 1.01874(7) 0.0465(5) Uani 1 1 d . . .
H11 H 0.4369 0.6376 1.0299 0.056 Uiso 1 1 calc R . .
O3 O 1.0749(3) 0.5308(2) 0.90472(6) 0.0835(7) Uani 1 1 d . . .
H6 H 1.0564 0.5686 0.9296 0.125 Uiso 1 1 calc R . .
C10 C 0.4688(4) 0.4942(2) 0.98331(8) 0.0522(6) Uani 1 1 d . . .
H10A H 0.5834 0.4467 1.0005 0.063 Uiso 1 1 calc R . .
H9B H 0.3616 0.4370 0.9688 0.063 Uiso 1 1 calc R . .
C17 C 0.3722(5) 0.5037(2) 1.10432(7) 0.0562(6) Uani 1 1 d . . .
C6 C 0.9210(4) 0.4763(2) 0.83019(7) 0.0455(5) Uani 1 1 d . . .
C7 C 0.8754(4) 0.5418(2) 0.87643(7) 0.0482(5) Uani 1 1 d . . .
H5 H 0.8480 0.6286 0.8698 0.058 Uiso 1 1 calc R . .
C13 C 0.0758(5) 0.4160(2) 1.05601(10) 0.0697(7) Uani 1 1 d . . .
H13 H 0.0009 0.4090 1.0268 0.084 Uiso 1 1 calc R . .
C5 C 1.0922(5) 0.3892(2) 0.82682(9) 0.0595(6) Uani 1 1 d . . .
H4 H 1.1770 0.3688 0.8538 0.071 Uiso 1 1 calc R . .
C2 C 0.8419(5) 0.4420(2) 0.74716(8) 0.0644(7) Uani 1 1 d . . .
H1 H 0.7561 0.4597 0.7200 0.077 Uiso 1 1 calc R . .
C18 C 0.5659(6) 0.5847(3) 1.11009(8) 0.0637(7) Uani 1 1 d . . .
C4 C 1.1411(5) 0.3315(3) 0.78448(10) 0.0711(7) Uani 1 1 d . . .
H3 H 1.2601 0.2743 0.7830 0.085 Uiso 1 1 calc R . .
C20 C 0.6051(5) 0.5870(2) 0.79086(9) 0.0614(7) Uani 1 1 d . . .
C19 C 0.7237(7) 0.6509(4) 1.11374(11) 0.0870(10) Uani 1 1 d . . .
C3 C 1.0161(5) 0.3578(3) 0.74466(9) 0.0698(7) Uani 1 1 d . . .
H2 H 1.0492 0.3188 0.7160 0.084 Uiso 1 1 calc R . .
C16 C 0.2975(7) 0.4302(3) 1.14191(10) 0.0841(10) Uani 1 1 d . . .
H16 H 0.3731 0.4341 1.1711 0.101 Uiso 1 1 calc R . .
C21 C 0.4500(7) 0.6547(3) 0.79086(12) 0.0931(10) Uani 1 1 d . . .
H18 H 0.3259 0.7089 0.7909 0.112 Uiso 1 1 calc R . .
C14 C 0.0030(6) 0.3462(3) 1.09366(14) 0.0873(9) Uani 1 1 d . . .
H14 H -0.1231 0.2940 1.0901 0.105 Uiso 1 1 calc R . .
C15 C 0.1144(7) 0.3530(3) 1.13615(14) 0.0988(11) Uani 1 1 d . . .
H15 H 0.0654 0.3046 1.1614 0.119 Uiso 1 1 calc R . .
H17 H 0.850(6) 0.704(3) 1.1173(12) 0.109(12) Uiso 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
C8 0.0587(14) 0.0514(13) 0.0471(12) -0.0070(10) 0.0031(11) -0.0064(12)
O2 0.0764(11) 0.0525(10) 0.0585(10) -0.0148(8) 0.0126(9) -0.0115(9)
O1 0.0770(11) 0.0631(10) 0.0403(8) -0.0110(7) -0.0125(8) 0.0247(9)
C9 0.0491(12) 0.0472(13) 0.0424(12) -0.0060(10) -0.0072(10) -0.0015(10)
C12 0.0525(12) 0.0459(12) 0.0456(12) -0.0025(10) 0.0034(10) 0.0093(11)
C1 0.0511(13) 0.0541(13) 0.0458(12) 0.0017(11) 0.0001(10) -0.0082(11)
C11 0.0570(13) 0.0452(12) 0.0373(11) -0.0037(9) -0.0049(10) 0.0028(11)
O3 0.0562(10) 0.1340(18) 0.0602(11) -0.0485(11) -0.0162(9) 0.0149(11)
C10 0.0593(13) 0.0511(13) 0.0463(12) -0.0010(10) 0.0031(10) 0.0099(11)
C17 0.0746(16) 0.0564(14) 0.0377(11) -0.0006(10) 0.0056(11) 0.0022(14)
C6 0.0420(12) 0.0503(12) 0.0441(12) -0.0072(9) 0.0025(9) -0.0111(10)
C7 0.0437(12) 0.0562(13) 0.0448(12) -0.0121(10) -0.0025(10) -0.0016(11)
C13 0.0671(17) 0.0655(16) 0.0763(18) 0.0017(14) -0.0018(15) -0.0035(14)
C5 0.0583(15) 0.0714(15) 0.0488(13) -0.0149(11) -0.0118(11) 0.0051(14)
C2 0.0742(17) 0.0795(17) 0.0394(13) -0.0022(12) -0.0021(12) -0.0032(15)
C18 0.0839(19) 0.0748(17) 0.0323(12) -0.0013(11) -0.0101(12) -0.0030(17)
C4 0.0666(17) 0.0810(18) 0.0656(16) -0.0231(14) -0.0040(15) 0.0112(16)
C20 0.0674(18) 0.0647(16) 0.0521(14) 0.0086(12) 0.0023(13) 0.0007(15)
C19 0.097(2) 0.102(3) 0.0618(18) -0.0056(17) -0.0186(17) -0.026(2)
C3 0.0786(18) 0.0797(18) 0.0512(15) -0.0203(14) 0.0057(14) 0.0014(16)
C16 0.126(3) 0.0791(19) 0.0472(15) 0.0107(14) 0.0015(17) -0.006(2)
C21 0.090(2) 0.091(2) 0.099(2) 0.0202(19) 0.0094(19) 0.030(2)
C14 0.082(2) 0.0715(19) 0.108(3) 0.0046(19) 0.016(2) -0.0152(17)
C15 0.134(3) 0.076(2) 0.086(2) 0.0188(18) 0.033(2) -0.017(2)

_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
C8 C9 1.502(3) . ?
C8 C7 1.505(3) . ?
C8 H7A 0.9700 . ?
C8 H8B 0.9700 . ?
O2 C9 1.199(3) . ?
O1 C11 1.423(3) . ?
O1 H12 0.8200 . ?
C9 C10 1.507(3) . ?
C12 C13 1.385(4) . ?
C12 C17 1.388(3) . ?
C12 C11 1.503(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.397(3) . ?
C1 C20 1.418(4) . ?
C11 C10 1.511(3) . ?
C11 H11 0.9800 . ?
O3 C7 1.405(3) . ?
O3 H6 0.8200 . ?
C10 H10A 0.9700 . ?
C10 H9B 0.9700 . ?
C17 C16 1.395(4) . ?
C17 C18 1.435(4) . ?
C6 C5 1.375(3) . ?
C6 C7 1.507(3) . ?
C7 H5 0.9800 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C5 C4 1.376(3) . ?
C5 H4 0.9300 . ?
C2 C3 1.365(4) . ?
C2 H1 0.9300 . ?
C18 C19 1.168(5) . ?
C4 C3 1.362(4) . ?
C4 H3 0.9300 . ?
C20 C21 1.161(4) . ?
C19 H17 0.94(4) . ?
C3 H2 0.9300 . ?
C16 C15 1.362(5) . ?
C16 H16 0.9300 . ?
C21 H18 0.9300 . ?
C14 C15 1.358(5) . ?
C14 H14 0.9300 . ?
C15 H15 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 C8 C7 114.40(18) . . ?
C9 C8 H7A 108.7 . . ?
C7 C8 H7A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H7A C8 H8B 107.6 . . ?
C11 O1 H12 109.5 . . ?
O2 C9 C8 121.0(2) . . ?
O2 C9 C10 122.18(19) . . ?
C8 C9 C10 116.80(18) . . ?
C13 C12 C17 118.6(2) . . ?
C13 C12 C11 119.8(2) . . ?
C17 C12 C11 121.6(2) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 C20 119.5(2) . . ?
C6 C1 C20 121.1(2) . . ?
O1 C11 C12 111.19(19) . . ?
O1 C11 C10 107.24(17) . . ?
C12 C11 C10 111.46(18) . . ?
O1 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C7 O3 H6 109.5 . . ?
C9 C10 C11 115.90(19) . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H9B 108.3 . . ?
C11 C10 H9B 108.3 . . ?
H10A C10 H9B 107.4 . . ?
C12 C17 C16 119.4(3) . . ?
C12 C17 C18 119.9(2) . . ?
C16 C17 C18 120.7(2) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C7 120.9(2) . . ?
C1 C6 C7 121.0(2) . . ?
O3 C7 C8 110.79(19) . . ?
O3 C7 C6 107.71(17) . . ?
C8 C7 C6 111.70(18) . . ?
O3 C7 H5 108.9 . . ?
C8 C7 H5 108.9 . . ?
C6 C7 H5 108.9 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H4 119.2 . . ?
C4 C5 H4 119.2 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H1 119.4 . . ?
C1 C2 H1 119.4 . . ?
C19 C18 C17 178.5(3) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H3 119.8 . . ?
C5 C4 H3 119.8 . . ?
C21 C20 C1 177.9(3) . . ?
C18 C19 H17 179(2) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H2 120.3 . . ?
C2 C3 H2 120.3 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C20 C21 H18 180.0 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035