# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Mal, Dipak'

_publ_contact_author_name        'Mal, Dipak'
_publ_contact_author_email       dmal@chem.iitkgp.ernet.in

_publ_section_title              
;
A rapid entry to C-prenylcarbazoles: total synthesis
of clausamine C-D, clausevatine D and clausine F
;

# Attachment '27.cif.txt'

data_dm_aj_pr
_database_code_depnum_ccdc_archive 'CCDC 770961'
#TrackingRef '27.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30.86 H30.86 N1.14 O3.43'
_chemical_formula_weight         472.59

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'
N N 0.0060 0.0030 '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   'C 2/c'
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                   13.752(2)
_cell_length_b                   15.076(3)
_cell_length_c                   21.810(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.944(6)
_cell_angle_gamma                90.00
_cell_volume                     4497.3(14)
_cell_formula_units_Z            7
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24843
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         24.35
_reflns_number_total             3664
_reflns_number_gt                2435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0599P)^2^+3.0861P] 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         3664
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003

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
N1 N 0.52526(14) 0.05233(12) 0.41980(8) 0.0552(5) Uani 1 1 d . . .
O4 O 0.67556(14) -0.05584(11) 0.48447(8) 0.0729(5) Uani 1 1 d . . .
C11 C 0.71899(17) 0.07227(15) 0.54967(10) 0.0542(6) Uani 1 1 d . . .
H11 H 0.7694 0.0413 0.5720 0.065 Uiso 1 1 calc R . .
C13 C 0.62760(17) 0.21069(14) 0.53313(10) 0.0489(6) Uani 1 1 d . . .
C12 C 0.70180(17) 0.16128(15) 0.56547(10) 0.0510(6) Uani 1 1 d . . .
C8 C 0.57030(16) 0.16735(14) 0.48506(10) 0.0481(5) Uani 1 1 d . . .
C15 C 0.48904(17) 0.19579(15) 0.44120(10) 0.0529(6) Uani 1 1 d . . .
O2 O 0.84815(13) 0.15513(13) 0.63132(8) 0.0737(5) Uani 1 1 d . . .
C9 C 0.58875(16) 0.07833(14) 0.46953(10) 0.0496(6) Uani 1 1 d . . .
C10 C 0.66366(18) 0.03003(15) 0.50245(10) 0.0537(6) Uani 1 1 d . . .
C31 C 0.76452(19) 0.20017(17) 0.61803(11) 0.0590(6) Uani 1 1 d . . .
C36 C 0.60777(19) 0.30706(15) 0.54594(11) 0.0611(7) Uani 1 1 d . . .
H36A H 0.6679 0.3349 0.5636 0.073 Uiso 1 1 calc R . .
H36B H 0.5871 0.3368 0.5073 0.073 Uiso 1 1 calc R . .
O1 O 0.74471(15) 0.26289(13) 0.64840(9) 0.0865(6) Uani 1 1 d . . .
C2 C 0.59866(18) -0.03504(16) 0.33968(10) 0.0569(6) Uani 1 1 d . . .
C14 C 0.46650(17) 0.12410(16) 0.40108(11) 0.0559(6) Uani 1 1 d . . .
C1 C 0.52495(19) -0.03107(16) 0.38618(11) 0.0651(7) Uani 1 1 d . . .
H1A H 0.4602 -0.0405 0.3650 0.078 Uiso 1 1 calc R . .
H1B H 0.5381 -0.0791 0.4155 0.078 Uiso 1 1 calc R . .
C19 C 0.3956(2) 0.1299(2) 0.35134(12) 0.0726(8) Uani 1 1 d . . .
H19 H 0.3832 0.0826 0.3243 0.087 Uiso 1 1 calc R . .
C7 C 0.6615(2) 0.03324(19) 0.33064(12) 0.0719(7) Uani 1 1 d . . .
H7 H 0.6597 0.0845 0.3542 0.086 Uiso 1 1 calc R . .
C3 C 0.6033(2) -0.11047(18) 0.30412(13) 0.0792(8) Uani 1 1 d . . .
H3 H 0.5618 -0.1579 0.3096 0.095 Uiso 1 1 calc R . .
C16 C 0.43317(19) 0.27324(17) 0.43246(12) 0.0651(7) Uani 1 1 d . . .
H16 H 0.4445 0.3209 0.4593 0.078 Uiso 1 1 calc R . .
C37 C 0.5307(2) 0.31922(17) 0.58920(13) 0.0788(8) Uani 1 1 d . . .
H37 H 0.4986 0.2682 0.6001 0.095 Uiso 1 1 calc R . .
C38 C 0.5039(2) 0.39334(19) 0.61326(13) 0.0783(8) Uani 1 1 d . . .
C18 C 0.3441(2) 0.2078(2) 0.34332(14) 0.0824(9) Uani 1 1 d . . .
H18 H 0.2966 0.2135 0.3100 0.099 Uiso 1 1 calc R . .
C32 C 0.9117(2) 0.1873(2) 0.68328(13) 0.0876(9) Uani 1 1 d . . .
H32A H 0.9692 0.1509 0.6890 0.131 Uiso 1 1 calc R . .
H32B H 0.8781 0.1851 0.7197 0.131 Uiso 1 1 calc R . .
H32C H 0.9302 0.2475 0.6757 0.131 Uiso 1 1 calc R . .
C50 C 0.7532(2) -0.10556(18) 0.51502(15) 0.0851(9) Uani 1 1 d . . .
H50A H 0.7527 -0.1643 0.4981 0.128 Uiso 1 1 calc R . .
H50B H 0.7454 -0.1088 0.5582 0.128 Uiso 1 1 calc R . .
H50C H 0.8143 -0.0773 0.5095 0.128 Uiso 1 1 calc R . .
C17 C 0.3612(2) 0.2781(2) 0.38372(14) 0.0789(8) Uani 1 1 d . . .
H17 H 0.3237 0.3293 0.3779 0.095 Uiso 1 1 calc R . .
C4 C 0.6693(3) -0.1160(2) 0.26045(15) 0.0994(11) Uani 1 1 d . . .
H4 H 0.6719 -0.1669 0.2366 0.119 Uiso 1 1 calc R . .
C6 C 0.7273(2) 0.0272(2) 0.28736(14) 0.0897(9) Uani 1 1 d . . .
H6 H 0.7697 0.0740 0.2821 0.108 Uiso 1 1 calc R . .
C40 C 0.4290(3) 0.3966(3) 0.65927(17) 0.1336(16) Uani 1 1 d . . .
H40A H 0.4198 0.4570 0.6715 0.200 Uiso 1 1 calc R . .
H40B H 0.4515 0.3619 0.6948 0.200 Uiso 1 1 calc R . .
H40C H 0.3680 0.3731 0.6407 0.200 Uiso 1 1 calc R . .
C5 C 0.7304(3) -0.0467(3) 0.25255(15) 0.1016(12) Uani 1 1 d . . .
H5 H 0.7744 -0.0503 0.2230 0.122 Uiso 1 1 calc R . .
C39 C 0.5445(3) 0.4798(2) 0.5964(3) 0.160(2) Uani 1 1 d . . .
H39A H 0.5167 0.5262 0.6191 0.240 Uiso 1 1 calc R . .
H39B H 0.5289 0.4899 0.5530 0.240 Uiso 1 1 calc R . .
H39C H 0.6142 0.4793 0.6060 0.240 Uiso 1 1 calc R . .

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
N1 0.0607(13) 0.0537(12) 0.0522(11) -0.0087(9) 0.0112(10) -0.0042(10)
O4 0.0938(14) 0.0496(10) 0.0757(12) -0.0098(9) 0.0100(10) 0.0130(9)
C11 0.0550(14) 0.0574(14) 0.0516(14) 0.0046(11) 0.0122(11) 0.0056(11)
C13 0.0570(14) 0.0460(12) 0.0465(12) 0.0005(10) 0.0181(11) -0.0038(11)
C12 0.0557(14) 0.0519(14) 0.0476(13) -0.0006(11) 0.0151(11) -0.0062(11)
C8 0.0524(13) 0.0467(13) 0.0477(13) 0.0012(10) 0.0177(11) 0.0002(11)
C15 0.0537(14) 0.0548(14) 0.0523(13) 0.0040(11) 0.0156(11) -0.0005(11)
O2 0.0631(11) 0.0951(14) 0.0614(11) -0.0057(10) -0.0010(9) -0.0042(10)
C9 0.0538(14) 0.0494(13) 0.0480(13) -0.0028(10) 0.0171(11) -0.0018(11)
C10 0.0655(16) 0.0452(13) 0.0535(14) -0.0021(11) 0.0204(12) 0.0031(12)
C31 0.0635(17) 0.0622(16) 0.0530(14) 0.0014(13) 0.0136(13) -0.0107(13)
C36 0.0784(18) 0.0483(14) 0.0581(15) -0.0014(11) 0.0146(13) -0.0031(12)
O1 0.0967(15) 0.0822(14) 0.0787(13) -0.0257(11) -0.0002(11) -0.0033(11)
C2 0.0635(16) 0.0609(15) 0.0459(13) -0.0050(11) 0.0031(12) 0.0101(13)
C14 0.0535(14) 0.0639(16) 0.0519(14) -0.0010(12) 0.0129(12) -0.0029(12)
C1 0.0718(17) 0.0607(15) 0.0640(16) -0.0163(12) 0.0128(13) -0.0110(13)
C19 0.0652(17) 0.090(2) 0.0622(17) -0.0042(15) 0.0049(14) -0.0120(16)
C7 0.0805(19) 0.0741(18) 0.0644(17) -0.0031(14) 0.0230(15) 0.0018(15)
C3 0.100(2) 0.0711(18) 0.0656(17) -0.0129(14) 0.0045(16) 0.0178(16)
C16 0.0641(17) 0.0641(16) 0.0686(17) 0.0065(13) 0.0142(14) 0.0097(13)
C37 0.110(2) 0.0524(16) 0.0803(19) -0.0005(14) 0.0395(17) 0.0094(15)
C38 0.085(2) 0.076(2) 0.0714(18) -0.0120(15) -0.0020(15) 0.0234(16)
C18 0.0657(19) 0.105(2) 0.0742(19) 0.0178(18) -0.0022(15) -0.0008(18)
C32 0.0724(19) 0.123(3) 0.0659(18) -0.0030(17) -0.0018(15) -0.0195(18)
C50 0.094(2) 0.0596(17) 0.105(2) 0.0062(16) 0.0266(19) 0.0253(16)
C17 0.0672(19) 0.085(2) 0.085(2) 0.0191(17) 0.0094(16) 0.0140(16)
C4 0.137(3) 0.094(3) 0.070(2) -0.0151(18) 0.020(2) 0.051(2)
C6 0.093(2) 0.102(2) 0.080(2) 0.0164(19) 0.0353(18) 0.0153(19)
C40 0.154(4) 0.158(4) 0.094(3) -0.013(2) 0.036(3) 0.078(3)
C5 0.118(3) 0.119(3) 0.073(2) 0.018(2) 0.036(2) 0.048(3)
C39 0.154(4) 0.068(2) 0.262(6) -0.048(3) 0.042(4) 0.002(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
N1 C9 1.377(3) . ?
N1 C14 1.386(3) . ?
N1 C1 1.455(3) . ?
O4 C10 1.368(3) . ?
O4 C50 1.414(3) . ?
C11 C10 1.372(3) . ?
C11 C12 1.411(3) . ?
C13 C12 1.395(3) . ?
C13 C8 1.406(3) . ?
C13 C36 1.510(3) . ?
C12 C31 1.482(3) . ?
C8 C9 1.414(3) . ?
C8 C15 1.458(3) . ?
C15 C16 1.400(3) . ?
C15 C14 1.405(3) . ?
O2 C31 1.341(3) . ?
O2 C32 1.442(3) . ?
C9 C10 1.398(3) . ?
C31 O1 1.202(3) . ?
C36 C37 1.501(3) . ?
C2 C7 1.372(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.508(3) . ?
C14 C19 1.384(3) . ?
C19 C18 1.374(4) . ?
C7 C6 1.376(4) . ?
C3 C4 1.384(4) . ?
C16 C17 1.377(4) . ?
C37 C38 1.304(3) . ?
C38 C39 1.479(5) . ?
C38 C40 1.512(4) . ?
C18 C17 1.382(4) . ?
C4 C5 1.362(5) . ?
C6 C5 1.351(5) . ?

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 N1 C14 108.22(18) . . ?
C9 N1 C1 127.7(2) . . ?
C14 N1 C1 123.7(2) . . ?
C10 O4 C50 118.3(2) . . ?
C10 C11 C12 122.0(2) . . ?
C12 C13 C8 116.9(2) . . ?
C12 C13 C36 123.9(2) . . ?
C8 C13 C36 119.2(2) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 C31 121.1(2) . . ?
C11 C12 C31 117.8(2) . . ?
C13 C8 C9 121.3(2) . . ?
C13 C8 C15 133.2(2) . . ?
C9 C8 C15 105.44(19) . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 C8 135.0(2) . . ?
C14 C15 C8 106.7(2) . . ?
C31 O2 C32 115.8(2) . . ?
N1 C9 C10 129.0(2) . . ?
N1 C9 C8 110.1(2) . . ?
C10 C9 C8 120.8(2) . . ?
O4 C10 C11 125.5(2) . . ?
O4 C10 C9 116.7(2) . . ?
C11 C10 C9 117.8(2) . . ?
O1 C31 O2 121.2(2) . . ?
O1 C31 C12 126.2(3) . . ?
O2 C31 C12 112.6(2) . . ?
C37 C36 C13 112.7(2) . . ?
C7 C2 C3 118.1(3) . . ?
C7 C2 C1 123.0(2) . . ?
C3 C2 C1 118.9(2) . . ?
C19 C14 N1 128.4(2) . . ?
C19 C14 C15 122.1(2) . . ?
N1 C14 C15 109.4(2) . . ?
N1 C1 C2 114.0(2) . . ?
C18 C19 C14 117.7(3) . . ?
C6 C7 C2 121.1(3) . . ?
C2 C3 C4 120.5(3) . . ?
C17 C16 C15 119.3(3) . . ?
C38 C37 C36 127.2(3) . . ?
C37 C38 C39 121.7(3) . . ?
C37 C38 C40 122.4(3) . . ?
C39 C38 C40 115.9(3) . . ?
C19 C18 C17 121.5(3) . . ?
C18 C17 C16 120.9(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C6 C7 120.1(3) . . ?
C6 C5 C4 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.030