# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Mugesh, Govindasamy'
_publ_contact_author_email       mugesh@ipc.iisc.ernet.in

_publ_section_title              
;
Synthesis, Characterization and Antioxidant Activity
of Angiotensin Converting Enzyme Inhibitors
;
loop_
_publ_author_name
G.Mugesh
B.Bhuyan

# Attachment 'Compound-15.cif'

data_compound15_0m
_database_code_depnum_ccdc_archive 'CCDC 775133'
#TrackingRef 'Compound-15.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C18 H28 N2 O6 Se2'

_chemical_formula_sum            'C18 H28 N2 O6 Se2'

_chemical_formula_weight         526.34

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'
N N 0.0061 0.0033 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P21

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   6.9783(3)

_cell_length_b                   11.2514(5)

_cell_length_c                   14.4801(7)

_cell_angle_alpha                90.00

_cell_angle_beta                 91.389(2)

_cell_angle_gamma                90.00

_cell_volume                     1136.58(9)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    3024

_cell_measurement_theta_min      2.3

_cell_measurement_theta_max      23.1

_exptl_crystal_description       rectangular

_exptl_crystal_colour            brown

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.538

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             532

_exptl_absorpt_coefficient_mu    3.287

_exptl_absorpt_correction_type   Empirical

_exptl_absorpt_correction_T_min  0.4063

_exptl_absorpt_correction_T_max  0.6865

_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      296(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            10037

_diffrn_reflns_av_R_equivalents  0.0466

_diffrn_reflns_av_sigmaI/netI    0.0622

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -15

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         2.29

_diffrn_reflns_theta_max         23.14

_reflns_number_total             3024

_reflns_number_gt                2350

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Ortep-3 for windows (Farrugia, 1997)'

_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0312P)^2^+0.0164P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.036(15)

_chemical_absolute_configuration syn

_refine_ls_number_reflns         3024

_refine_ls_number_parameters     255

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0587

_refine_ls_R_factor_gt           0.0380

_refine_ls_wR_factor_ref         0.0775

_refine_ls_wR_factor_gt          0.0708

_refine_ls_goodness_of_fit_ref   1.036

_refine_ls_restrained_S_all      1.036

_refine_ls_shift/su_max          0.004

_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

Se01 Se 1.05820(8) 0.13348(6) 0.20370(5) 0.0618(2) Uani 1 1 d . . .
C13 C 0.4898(11) 0.3831(8) 0.1984(5) 0.088(3) Uani 1 1 d . . .
H5A H 0.3638 0.3677 0.2207 0.132 Uiso 1 1 calc R . .
H5B H 0.4910 0.3697 0.1329 0.132 Uiso 1 1 calc R . .
H5C H 0.5243 0.4641 0.2114 0.132 Uiso 1 1 calc R . .
C11 C 0.6312(9) 0.3013(6) 0.2457(4) 0.0496(16) Uani 1 1 d . . .
H4 H 0.7599 0.3226 0.2258 0.060 Uiso 1 1 calc R . .
C12 C 0.6234(10) 0.3200(6) 0.3483(5) 0.0576(19) Uani 1 1 d . . .
C10 C 0.5951(8) 0.1739(6) 0.2209(4) 0.0578(19) Uani 1 1 d . . .
H6A H 0.5904 0.1671 0.1541 0.069 Uiso 1 1 calc R . .
H6B H 0.4701 0.1515 0.2431 0.069 Uiso 1 1 calc R . .
O04 O 0.4845(7) 0.2825(5) 0.3905(4) 0.0824(16) Uani 1 1 d . . .
N1 N 0.7611(9) 0.3805(5) 0.3919(4) 0.0657(16) Uani 1 1 d . . .
C17 C 0.7580(12) 0.4076(8) 0.4892(5) 0.081(2) Uani 1 1 d . . .
H13 H 0.6921 0.3445 0.5227 0.097 Uiso 1 1 calc R . .
C03 C 1.2462(9) -0.0775(6) 0.0746(4) 0.0480(16) Uani 1 1 d . . .
O01 O 1.3857(6) -0.0300(4) 0.0354(3) 0.0669(13) Uani 1 1 d . . .
O03 O 1.4516(7) -0.3442(5) 0.0497(3) 0.0792(15) Uani 1 1 d . . .
H9 H 1.5148 -0.3907 0.0192 0.119 Uiso 1 1 calc R . .
N01 N 1.2825(7) -0.1612(4) 0.1382(4) 0.0479(13) Uani 1 1 d . . .
O02 O 1.7298(10) -0.3046(8) 0.1058(6) 0.176(4) Uani 1 1 d . . .
C09 C 1.5619(13) -0.2852(7) 0.1022(6) 0.069(2) Uani 1 1 d . . .
C08 C 1.4772(10) -0.1967(6) 0.1627(5) 0.0556(18) Uani 1 1 d . . .
H16 H 1.5590 -0.1259 0.1639 0.067 Uiso 1 1 calc R . .
C18 C 0.6548(12) 0.5313(11) 0.5039(6) 0.101(4) Uani 1 1 d . . .
O06 O 0.6388(9) 0.5530(8) 0.5868(5) 0.157(3) Uani 1 1 d . . .
H6 H 0.5855 0.6173 0.5930 0.235 Uiso 1 1 calc R . .
O05 O 0.5939(14) 0.5857(7) 0.4404(6) 0.163(3) Uani 1 1 d . . .
C14 C 0.9445(12) 0.4234(9) 0.3538(7) 0.107(3) Uani 1 1 d . . .
H21A H 1.0130 0.3586 0.3252 0.128 Uiso 1 1 calc R . .
H21B H 0.9210 0.4849 0.3080 0.128 Uiso 1 1 calc R . .
C15 C 1.0560(14) 0.4711(12) 0.4337(8) 0.138(4) Uani 1 1 d . . .
H22A H 1.0440 0.5569 0.4372 0.165 Uiso 1 1 calc R . .
H22B H 1.1906 0.4506 0.4296 0.165 Uiso 1 1 calc R . .
C16 C 0.9667(16) 0.4115(11) 0.5173(8) 0.133(4) Uani 1 1 d . . .
H23A H 1.0179 0.3322 0.5272 0.160 Uiso 1 1 calc R . .
H23B H 0.9873 0.4582 0.5730 0.160 Uiso 1 1 calc R . .
C01 C 1.0157(9) 0.0887(5) 0.0746(4) 0.063(2) Uani 1 1 d . . .
H24A H 0.8859 0.1106 0.0561 0.075 Uiso 1 1 calc R . .
H24B H 1.1023 0.1344 0.0371 0.075 Uiso 1 1 calc R . .
C02 C 1.0439(9) -0.0418(5) 0.0537(5) 0.0574(18) Uani 1 1 d . . .
H25 H 0.9572 -0.0894 0.0910 0.069 Uiso 1 1 calc R . .
C04 C 0.9973(12) -0.0626(7) -0.0499(5) 0.094(3) Uani 1 1 d . . .
H26A H 1.0848 -0.0178 -0.0864 0.141 Uiso 1 1 calc R . .
H26B H 0.8685 -0.0373 -0.0638 0.141 Uiso 1 1 calc R . .
H26C H 1.0098 -0.1456 -0.0638 0.141 Uiso 1 1 calc R . .
Se02 Se 0.78400(9) 0.06053(5) 0.26967(5) 0.0614(2) Uani 1 1 d . . .
C06 C 1.2651(12) -0.2943(8) 0.2614(5) 0.092(3) Uani 1 1 d . . .
H28A H 1.2164 -0.2938 0.3235 0.110 Uiso 1 1 calc R . .
H28B H 1.2665 -0.3757 0.2392 0.110 Uiso 1 1 calc R . .
C07 C 1.4600(11) -0.2427(7) 0.2603(5) 0.081(2) Uani 1 1 d . . .
H29A H 1.5565 -0.3026 0.2740 0.097 Uiso 1 1 calc R . .
H29B H 1.4734 -0.1786 0.3048 0.097 Uiso 1 1 calc R . .
C05 C 1.1432(10) -0.2182(7) 0.1989(5) 0.075(2) Uani 1 1 d . . .
H27A H 1.0521 -0.2660 0.1634 0.090 Uiso 1 1 calc R . .
H27B H 1.0738 -0.1594 0.2339 0.090 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

Se01 0.0415(4) 0.0632(5) 0.0803(5) -0.0139(4) -0.0037(3) 0.0061(3)
C13 0.086(6) 0.098(7) 0.080(6) 0.013(5) 0.002(5) 0.028(5)
C11 0.048(4) 0.049(4) 0.052(5) 0.001(3) 0.005(3) 0.003(3)
C12 0.057(5) 0.048(4) 0.068(6) 0.008(4) 0.013(4) 0.008(4)
C10 0.042(4) 0.068(5) 0.063(4) -0.008(4) -0.002(3) 0.003(3)
O04 0.084(4) 0.078(4) 0.088(4) -0.012(3) 0.036(3) -0.015(3)
N1 0.078(5) 0.064(4) 0.056(4) -0.012(3) 0.007(3) -0.008(4)
C17 0.101(7) 0.073(6) 0.069(6) -0.011(5) 0.009(5) -0.004(5)
C03 0.062(5) 0.033(4) 0.049(4) -0.003(3) 0.008(4) 0.006(3)
O01 0.069(3) 0.054(3) 0.079(4) 0.022(3) 0.026(3) 0.013(2)
O03 0.088(3) 0.062(4) 0.089(4) -0.029(3) 0.015(3) -0.005(3)
N01 0.048(3) 0.038(3) 0.058(4) 0.010(3) 0.003(3) 0.002(3)
O02 0.078(5) 0.219(9) 0.232(9) -0.095(7) 0.019(5) 0.048(5)
C09 0.065(5) 0.053(5) 0.092(6) -0.001(5) 0.022(5) 0.005(4)
C08 0.062(5) 0.039(4) 0.065(5) -0.001(4) -0.005(4) 0.000(4)
C18 0.095(6) 0.165(12) 0.044(6) -0.039(6) 0.012(5) 0.008(7)
O06 0.163(6) 0.213(8) 0.093(5) -0.068(5) -0.009(4) 0.056(6)
O05 0.247(10) 0.121(7) 0.121(7) -0.008(5) 0.018(6) 0.047(6)
C14 0.079(6) 0.121(8) 0.122(8) -0.039(7) 0.041(6) -0.052(6)
C15 0.079(7) 0.169(11) 0.166(12) -0.055(10) 0.003(7) -0.042(7)
C16 0.113(9) 0.154(11) 0.130(10) -0.039(8) -0.039(7) 0.037(8)
C01 0.052(4) 0.065(6) 0.072(5) 0.013(4) 0.003(3) 0.018(3)
C02 0.068(5) 0.041(4) 0.063(5) 0.004(3) 0.007(4) 0.004(3)
C04 0.116(7) 0.065(6) 0.100(7) -0.025(5) -0.025(5) 0.000(5)
Se02 0.0606(4) 0.0525(4) 0.0711(5) 0.0016(4) 0.0003(3) 0.0029(4)
C06 0.115(7) 0.081(6) 0.082(6) 0.035(5) 0.042(5) 0.017(6)
C07 0.102(7) 0.079(6) 0.061(6) 0.010(4) -0.004(4) 0.006(5)
C05 0.081(5) 0.056(5) 0.090(6) 0.028(4) 0.031(5) 0.012(4)

_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

Se01 C01 1.952(6) . ?
Se01 Se02 2.3100(9) . ?
C13 C11 1.502(9) . ?
C13 H5A 0.9600 . ?
C13 H5B 0.9600 . ?
C13 H5C 0.9600 . ?
C11 C10 1.498(9) . ?
C11 C12 1.501(9) . ?
C11 H4 0.9800 . ?
C12 O04 1.233(7) . ?
C12 N1 1.326(8) . ?
C10 Se02 1.953(6) . ?
C10 H6A 0.9700 . ?
C10 H6B 0.9700 . ?
N1 C17 1.442(8) . ?
N1 C14 1.486(9) . ?
C17 C16 1.503(12) . ?
C17 C18 1.585(13) . ?
C17 H13 0.9800 . ?
C03 O01 1.258(7) . ?
C03 N01 1.337(8) . ?
C03 C02 1.492(9) . ?
O03 C09 1.258(8) . ?
O03 H9 0.8200 . ?
N01 C08 1.452(8) . ?
N01 C05 1.473(8) . ?
O02 C09 1.192(8) . ?
C09 C08 1.460(10) . ?
C08 C07 1.512(9) . ?
C08 H16 0.9800 . ?
C18 O05 1.175(10) . ?
C18 O06 1.233(9) . ?
O06 H6 0.8200 . ?
C14 C15 1.480(11) . ?
C14 H21A 0.9700 . ?
C14 H21B 0.9700 . ?
C15 C16 1.530(14) . ?
C15 H22A 0.9700 . ?
C15 H22B 0.9700 . ?
C16 H23A 0.9700 . ?
C16 H23B 0.9700 . ?
C01 C02 1.513(8) . ?
C01 H24A 0.9700 . ?
C01 H24B 0.9700 . ?
C02 C04 1.544(8) . ?
C02 H25 0.9800 . ?
C04 H26A 0.9600 . ?
C04 H26B 0.9600 . ?
C04 H26C 0.9600 . ?
C06 C07 1.480(10) . ?
C06 C05 1.496(10) . ?
C06 H28A 0.9700 . ?
C06 H28B 0.9700 . ?
C07 H29A 0.9700 . ?
C07 H29B 0.9700 . ?
C05 H27A 0.9700 . ?
C05 H27B 0.9700 . ?

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

C01 Se01 Se02 101.31(19) . . ?
C11 C13 H5A 109.5 . . ?
C11 C13 H5B 109.5 . . ?
H5A C13 H5B 109.5 . . ?
C11 C13 H5C 109.5 . . ?
H5A C13 H5C 109.5 . . ?
H5B C13 H5C 109.5 . . ?
C10 C11 C12 111.2(5) . . ?
C10 C11 C13 111.9(6) . . ?
C12 C11 C13 109.1(5) . . ?
C10 C11 H4 108.2 . . ?
C12 C11 H4 108.2 . . ?
C13 C11 H4 108.2 . . ?
O04 C12 N1 120.5(7) . . ?
O04 C12 C11 119.4(7) . . ?
N1 C12 C11 120.0(6) . . ?
C11 C10 Se02 115.5(4) . . ?
C11 C10 H6A 108.4 . . ?
Se02 C10 H6A 108.4 . . ?
C11 C10 H6B 108.4 . . ?
Se02 C10 H6B 108.4 . . ?
H6A C10 H6B 107.5 . . ?
C12 N1 C17 123.1(6) . . ?
C12 N1 C14 127.6(6) . . ?
C17 N1 C14 109.2(6) . . ?
N1 C17 C16 103.5(7) . . ?
N1 C17 C18 109.5(7) . . ?
C16 C17 C18 112.2(8) . . ?
N1 C17 H13 110.5 . . ?
C16 C17 H13 110.5 . . ?
C18 C17 H13 110.5 . . ?
O01 C03 N01 118.3(6) . . ?
O01 C03 C02 122.2(6) . . ?
N01 C03 C02 119.5(6) . . ?
C09 O03 H9 109.5 . . ?
C03 N01 C08 121.5(5) . . ?
C03 N01 C05 127.0(5) . . ?
C08 N01 C05 111.2(5) . . ?
O02 C09 O03 121.1(8) . . ?
O02 C09 C08 120.6(8) . . ?
O03 C09 C08 118.1(7) . . ?
N01 C08 C09 115.6(6) . . ?
N01 C08 C07 103.1(5) . . ?
C09 C08 C07 111.7(6) . . ?
N01 C08 H16 108.7 . . ?
C09 C08 H16 108.7 . . ?
C07 C08 H16 108.7 . . ?
O05 C18 O06 128.3(11) . . ?
O05 C18 C17 120.6(8) . . ?
O06 C18 C17 110.9(10) . . ?
C18 O06 H6 109.5 . . ?
C15 C14 N1 105.6(7) . . ?
C15 C14 H21A 110.6 . . ?
N1 C14 H21A 110.6 . . ?
C15 C14 H21B 110.6 . . ?
N1 C14 H21B 110.6 . . ?
H21A C14 H21B 108.8 . . ?
C14 C15 C16 104.0(8) . . ?
C14 C15 H22A 110.9 . . ?
C16 C15 H22A 110.9 . . ?
C14 C15 H22B 110.9 . . ?
C16 C15 H22B 110.9 . . ?
H22A C15 H22B 109.0 . . ?
C17 C16 C15 102.1(8) . . ?
C17 C16 H23A 111.4 . . ?
C15 C16 H23A 111.4 . . ?
C17 C16 H23B 111.4 . . ?
C15 C16 H23B 111.4 . . ?
H23A C16 H23B 109.2 . . ?
C02 C01 Se01 115.1(4) . . ?
C02 C01 H24A 108.5 . . ?
Se01 C01 H24A 108.5 . . ?
C02 C01 H24B 108.5 . . ?
Se01 C01 H24B 108.5 . . ?
H24A C01 H24B 107.5 . . ?
C03 C02 C01 110.4(5) . . ?
C03 C02 C04 109.4(5) . . ?
C01 C02 C04 108.4(5) . . ?
C03 C02 H25 109.5 . . ?
C01 C02 H25 109.5 . . ?
C04 C02 H25 109.5 . . ?
C02 C04 H26A 109.5 . . ?
C02 C04 H26B 109.5 . . ?
H26A C04 H26B 109.5 . . ?
C02 C04 H26C 109.5 . . ?
H26A C04 H26C 109.5 . . ?
H26B C04 H26C 109.5 . . ?
C10 Se02 Se01 100.20(19) . . ?
C07 C06 C05 106.1(6) . . ?
C07 C06 H28A 110.5 . . ?
C05 C06 H28A 110.5 . . ?
C07 C06 H28B 110.5 . . ?
C05 C06 H28B 110.5 . . ?
H28A C06 H28B 108.7 . . ?
C06 C07 C08 103.8(6) . . ?
C06 C07 H29A 111.0 . . ?
C08 C07 H29A 111.0 . . ?
C06 C07 H29B 111.0 . . ?
C08 C07 H29B 111.0 . . ?
H29A C07 H29B 109.0 . . ?
N01 C05 C06 103.7(6) . . ?
N01 C05 H27A 111.0 . . ?
C06 C05 H27A 111.0 . . ?
N01 C05 H27B 111.0 . . ?
C06 C05 H27B 111.0 . . ?
H27A C05 H27B 109.0 . . ?

_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        23.14

_diffrn_measured_fraction_theta_full 0.998

_refine_diff_density_max         0.526

_refine_diff_density_min         -0.292

_refine_diff_density_rms         0.060

# Attachment 'Compound-13.cif'

data_compound13_0m
_database_code_depnum_ccdc_archive 'CCDC 797125'
#TrackingRef 'Compound-13.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C21 H36 Br N2 O3'

_chemical_formula_sum            'C21 H36 Br N2 O3'

_chemical_formula_weight         444.43

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P1

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'

_cell_length_a                   5.3658(11)

_cell_length_b                   10.1748(18)

_cell_length_c                   10.905(2)

_cell_angle_alpha                82.918(11)

_cell_angle_beta                 88.385(11)

_cell_angle_gamma                78.119(12)

_cell_volume                     578.16(19)

_cell_formula_units_Z            1

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      1.88

_cell_measurement_theta_max      25.44

_exptl_crystal_description       rectangular

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.29

_exptl_crystal_size_mid          0.21

_exptl_crystal_size_min          0.18

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.276

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             235

_exptl_absorpt_coefficient_mu    1.799

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.588

_exptl_absorpt_correction_T_max  0.723

_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      296(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  'Bruker Smart CCD Area Detector'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.3

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            7602

_diffrn_reflns_av_R_equivalents  0.0345

_diffrn_reflns_av_sigmaI/netI    0.0969

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       6

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       13

_diffrn_reflns_theta_min         1.88

_diffrn_reflns_theta_max         25.44

_reflns_number_total             3881

_reflns_number_gt                1812

_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, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'

_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.1980P)^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     SHELXL

_refine_ls_extinction_coef       0.033(3)

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.21(3)

_chemical_absolute_configuration syn

_refine_ls_number_reflns         3881

_refine_ls_number_parameters     255

_refine_ls_number_restraints     3

_refine_ls_R_factor_all          0.1794

_refine_ls_R_factor_gt           0.0950

_refine_ls_wR_factor_ref         0.3022

_refine_ls_wR_factor_gt          0.2661

_refine_ls_goodness_of_fit_ref   0.921

_refine_ls_restrained_S_all      0.921

_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

Br1A Br -0.0491(3) 0.70179(18) 0.79805(19) 0.1362(11) Uani 0.828(6) 1 d P A 1
Br1B Br -0.383(2) 0.6863(11) 0.6303(12) 0.134(5) Uani 0.172(6) 1 d P A 2
C13 C 0.0820(17) 0.1944(11) 0.8887(8) 0.058(3) Uani 1 1 d . . .
H13 H -0.0984 0.2387 0.8848 0.069 Uiso 1 1 calc R . .
C2 C 0.878(2) 0.1900(11) 0.3800(9) 0.066(3) Uani 1 1 d . . .
H2A H 1.0335 0.1760 0.3318 0.079 Uiso 1 1 calc R . .
H2B H 0.8587 0.2770 0.4108 0.079 Uiso 1 1 calc R . .
C9 C 0.308(2) 0.7259(11) 0.1783(11) 0.082(4) Uani 1 1 d . . .
H9A H 0.2893 0.8190 0.1948 0.099 Uiso 1 1 calc R . .
H9B H 0.1710 0.7218 0.1235 0.099 Uiso 1 1 calc R . .
C19 C 0.143(4) 0.5374(17) 0.742(2) 0.136(6) Uani 1 1 d . . .
H19A H 0.2309 0.5603 0.6656 0.163 Uiso 1 1 calc R A 1
H19B H 0.2708 0.4936 0.8030 0.163 Uiso 1 1 calc R A 1
C12 C 0.221(2) 0.2500(11) 0.9882(11) 0.065(3) Uani 1 1 d . . .
C11 C 0.607(2) 0.5318(11) 0.0943(10) 0.076(3) Uani 1 1 d . . .
H11A H 0.4819 0.5188 0.0371 0.091 Uiso 1 1 calc R . .
H11B H 0.7748 0.5057 0.0581 0.091 Uiso 1 1 calc R . .
C14 C 0.110(2) 0.0393(11) 0.9161(11) 0.070(3) Uani 1 1 d . . .
H14A H 0.1002 0.0115 1.0041 0.084 Uiso 1 1 calc R . .
H14B H -0.0197 0.0084 0.8740 0.084 Uiso 1 1 calc R . .
C8 C 0.285(2) 0.6378(11) 0.2975(12) 0.079(3) Uani 1 1 d . . .
H8A H 0.1175 0.6646 0.3329 0.095 Uiso 1 1 calc R . .
H8B H 0.4107 0.6486 0.3559 0.095 Uiso 1 1 calc R . .
C16 C 0.389(2) 0.0811(12) 0.7505(9) 0.075(3) Uani 1 1 d . . .
H16A H 0.5584 0.1009 0.7427 0.090 Uiso 1 1 calc R . .
H16B H 0.3532 0.0416 0.6780 0.090 Uiso 1 1 calc R . .
C1 C 0.6539(18) 0.1938(10) 0.2961(9) 0.058(2) Uani 1 1 d . . .
H1 H 0.4986 0.2160 0.3453 0.070 Uiso 1 1 calc R . .
C18 C -0.018(2) 0.4430(11) 0.7204(16) 0.101(5) Uani 1 1 d . A .
H18 H -0.1253 0.4215 0.7913 0.121 Uiso 1 1 calc R . .
C17 C 0.172(2) 0.3172(11) 0.6804(10) 0.071(3) Uani 1 1 d . . .
C7 C 0.3299(18) 0.4870(11) 0.2727(11) 0.070(3) Uani 1 1 d . . .
H7A H 0.3206 0.4297 0.3500 0.083 Uiso 1 1 calc R . .
H7B H 0.1978 0.4753 0.2186 0.083 Uiso 1 1 calc R . .
C4 C 0.902(2) -0.0558(13) 0.4447(11) 0.081(3) Uani 1 1 d . . .
H4A H 0.9002 -0.1218 0.5168 0.097 Uiso 1 1 calc R . .
H4B H 1.0581 -0.0840 0.3994 0.097 Uiso 1 1 calc R . .
C6 C 0.5906(19) 0.4451(10) 0.2129(9) 0.059(2) Uani 1 1 d . . .
H6 H 0.7221 0.4568 0.2688 0.071 Uiso 1 1 calc R . .
C5 C 0.673(3) -0.0550(14) 0.3620(16) 0.104(5) Uani 1 1 d . . .
H5A H 0.6931 -0.1412 0.3296 0.124 Uiso 1 1 calc R . .
H5B H 0.5170 -0.0414 0.4101 0.124 Uiso 1 1 calc R . .
C3 C 0.902(3) 0.0819(12) 0.4872(9) 0.081(3) Uani 1 1 d . . .
H3A H 0.7607 0.1039 0.5438 0.097 Uiso 1 1 calc R . .
H3B H 1.0584 0.0776 0.5310 0.097 Uiso 1 1 calc R . .
C10 C 0.560(3) 0.6829(13) 0.1151(14) 0.089(4) Uani 1 1 d . . .
H10A H 0.6960 0.6975 0.1653 0.107 Uiso 1 1 calc R . .
H10B H 0.5622 0.7381 0.0360 0.107 Uiso 1 1 calc R . .
C15 C 0.365(3) -0.0123(15) 0.8675(15) 0.111(5) Uani 1 1 d . . .
H15A H 0.3800 -0.1046 0.8495 0.133 Uiso 1 1 calc R . .
H15B H 0.4950 -0.0098 0.9265 0.133 Uiso 1 1 calc R . .
O3 O 0.3030(17) 0.3148(10) 0.5840(7) 0.100(3) Uani 1 1 d . A .
O2 O 0.1281(13) 0.2550(9) 1.0885(7) 0.080(2) Uani 1 1 d . . .
O1 O 0.4249(16) 0.2834(10) 0.9534(7) 0.087(2) Uani 1 1 d . . .
N1 N 0.6368(15) 0.2998(8) 0.1911(7) 0.058(2) Uani 1 1 d . . .
H1A H 0.5112 0.2905 0.1419 0.070 Uiso 1 1 calc R . .
H1B H 0.7829 0.2825 0.1480 0.070 Uiso 1 1 calc R . .
N2 N 0.1962(14) 0.2043(10) 0.7663(7) 0.065(2) Uani 1 1 d . A .
C20 C 0.658(2) 0.0594(10) 0.2551(11) 0.073(3) Uani 1 1 d . . .
H20A H 0.8041 0.0376 0.2011 0.087 Uiso 1 1 calc R . .
H20B H 0.5061 0.0646 0.2074 0.087 Uiso 1 1 calc R . .
C21 C -0.182(3) 0.5046(17) 0.5911(16) 0.113(5) Uani 1 1 d . . .
H21A H -0.2937 0.4461 0.5727 0.136 Uiso 1 1 calc R A 2
H21B H -0.0680 0.5156 0.5215 0.136 Uiso 1 1 calc R A 2

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

Br1A 0.215(3) 0.0753(11) 0.1129(15) -0.0304(10) 0.0266(13) -0.0105(11)
Br1B 0.112(8) 0.113(8) 0.164(10) 0.019(7) 0.019(6) -0.017(5)
C13 0.041(5) 0.096(8) 0.041(5) -0.023(5) 0.009(4) -0.017(5)
C2 0.082(7) 0.064(6) 0.056(6) -0.011(5) -0.025(5) -0.024(5)
C9 0.097(9) 0.055(7) 0.085(8) 0.004(6) -0.021(7) 0.003(6)
C19 0.152(15) 0.096(12) 0.165(17) -0.043(11) -0.020(12) -0.019(11)
C12 0.054(7) 0.073(7) 0.060(7) -0.019(5) -0.013(5) 0.015(5)
C11 0.084(8) 0.068(7) 0.062(7) 0.007(6) -0.016(5) 0.008(5)
C14 0.072(7) 0.068(7) 0.075(7) -0.011(6) -0.008(5) -0.022(5)
C8 0.084(8) 0.055(6) 0.099(9) -0.018(6) -0.011(6) -0.011(6)
C16 0.078(7) 0.090(8) 0.042(5) -0.003(6) 0.003(5) 0.018(6)
C1 0.048(5) 0.066(6) 0.067(6) -0.020(5) -0.003(4) -0.020(4)
C18 0.057(7) 0.047(6) 0.194(15) -0.003(8) -0.033(8) 0.000(5)
C17 0.083(8) 0.072(7) 0.060(7) 0.007(6) -0.018(6) -0.025(6)
C7 0.056(6) 0.077(7) 0.072(7) -0.002(6) 0.013(5) -0.011(5)
C4 0.084(8) 0.079(8) 0.075(7) -0.003(6) 0.014(6) -0.010(6)
C6 0.058(6) 0.060(6) 0.060(6) -0.010(5) -0.007(4) -0.011(4)
C5 0.082(8) 0.074(8) 0.155(14) 0.004(9) -0.028(9) -0.024(7)
C3 0.119(9) 0.085(9) 0.036(5) 0.010(6) 0.005(5) -0.024(7)
C10 0.084(8) 0.072(8) 0.104(9) 0.000(7) 0.013(7) -0.012(6)
C15 0.125(12) 0.076(9) 0.115(11) 0.022(8) 0.008(9) -0.003(8)
O3 0.129(7) 0.118(7) 0.043(4) 0.001(4) 0.038(4) -0.015(5)
O2 0.068(5) 0.121(7) 0.045(4) -0.029(4) -0.008(4) 0.010(4)
O1 0.061(5) 0.131(7) 0.079(5) -0.035(5) -0.008(4) -0.028(5)
N1 0.062(5) 0.058(5) 0.054(5) -0.013(4) -0.012(4) -0.005(4)
N2 0.048(5) 0.092(6) 0.056(5) -0.026(5) -0.010(4) -0.005(4)
C20 0.067(7) 0.054(6) 0.091(8) 0.006(6) -0.041(6) -0.002(5)
C21 0.105(10) 0.104(11) 0.128(12) 0.003(9) 0.001(9) -0.024(8)

_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

Br1A C19 1.935(18) . ?
Br1B C21 2.03(2) . ?
C13 N2 1.453(12) . ?
C13 C14 1.546(15) . ?
C13 C12 1.556(14) . ?
C13 H13 0.9800 . ?
C2 C3 1.492(15) . ?
C2 C1 1.521(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C9 C8 1.502(17) . ?
C9 C10 1.508(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C19 C18 1.46(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C12 O2 1.191(13) . ?
C12 O1 1.248(14) . ?
C11 C6 1.484(14) . ?
C11 C10 1.550(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 C15 1.466(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C8 C7 1.560(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 N2 1.476(13) . ?
C16 C15 1.514(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 N1 1.463(13) . ?
C1 C20 1.486(14) . ?
C1 H1 0.9800 . ?
C18 C17 1.564(18) . ?
C18 C21 1.67(2) . ?
C18 H18 0.9800 . ?
C17 O3 1.248(13) . ?
C17 N2 1.377(14) . ?
C7 C6 1.528(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 C3 1.529(17) . ?
C4 C5 1.542(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 N1 1.496(12) . ?
C6 H6 0.9800 . ?
C5 C20 1.534(18) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?

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

N2 C13 C14 100.2(8) . . ?
N2 C13 C12 114.5(8) . . ?
C14 C13 C12 110.9(8) . . ?
N2 C13 H13 110.3 . . ?
C14 C13 H13 110.3 . . ?
C12 C13 H13 110.3 . . ?
C3 C2 C1 113.6(9) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C8 C9 C10 112.0(9) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C18 C19 Br1A 112.4(13) . . ?
C18 C19 H19A 109.1 . . ?
Br1A C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
Br1A C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
O2 C12 O1 126.4(10) . . ?
O2 C12 C13 118.6(11) . . ?
O1 C12 C13 115.0(9) . . ?
C6 C11 C10 110.7(10) . . ?
C6 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C15 C14 C13 103.0(9) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C9 C8 C7 109.5(10) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N2 C16 C15 103.6(9) . . ?
N2 C16 H16A 111.0 . . ?
C15 C16 H16A 111.0 . . ?
N2 C16 H16B 111.0 . . ?
C15 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
N1 C1 C20 111.6(8) . . ?
N1 C1 C2 112.4(8) . . ?
C20 C1 C2 111.6(8) . . ?
N1 C1 H1 107.0 . . ?
C20 C1 H1 107.0 . . ?
C2 C1 H1 107.0 . . ?
C19 C18 C17 104.3(11) . . ?
C19 C18 C21 107.6(14) . . ?
C17 C18 C21 102.4(12) . . ?
C19 C18 H18 113.8 . . ?
C17 C18 H18 113.8 . . ?
C21 C18 H18 113.8 . . ?
O3 C17 N2 120.4(11) . . ?
O3 C17 C18 126.0(11) . . ?
N2 C17 C18 113.5(11) . . ?
C6 C7 C8 110.2(9) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C3 C4 C5 113.2(10) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C11 C6 N1 109.9(8) . . ?
C11 C6 C7 110.2(8) . . ?
N1 C6 C7 110.5(8) . . ?
C11 C6 H6 108.7 . . ?
N1 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C20 C5 C4 109.1(9) . . ?
C20 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
C20 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C2 C3 C4 111.1(9) . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C9 C10 C11 111.3(10) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C14 C15 C16 105.1(10) . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C1 N1 C6 120.0(7) . . ?
C1 N1 H1A 107.3 . . ?
C6 N1 H1A 107.3 . . ?
C1 N1 H1B 107.3 . . ?
C6 N1 H1B 107.3 . . ?
H1A N1 H1B 106.9 . . ?
C17 N2 C13 127.4(9) . . ?
C17 N2 C16 120.8(9) . . ?
C13 N2 C16 110.9(8) . . ?
C1 C20 C5 113.6(10) . . ?
C1 C20 H20A 108.8 . . ?
C5 C20 H20A 108.8 . . ?
C1 C20 H20B 108.8 . . ?
C5 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C18 C21 Br1B 103.3(11) . . ?
C18 C21 H21A 111.1 . . ?
Br1B C21 H21A 111.1 . . ?
C18 C21 H21B 111.1 . . ?
Br1B C21 H21B 111.1 . . ?
H21A C21 H21B 109.1 . . ?

_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        25.44

_diffrn_measured_fraction_theta_full 0.994

_refine_diff_density_max         0.878

_refine_diff_density_min         -0.362

_refine_diff_density_rms         0.113

# Attachment 'Compound-20.cif'

data_compound20_0m
_database_code_depnum_ccdc_archive 'CCDC 797126'
#TrackingRef 'Compound-20.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C10 H12 O3 Se'

_chemical_formula_sum            'C10 H12 O3 Se'

_chemical_formula_weight         259.16

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   P21ab

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   5.7334(9)

_cell_length_b                   7.8990(12)

_cell_length_c                   47.642(7)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     2157.6(6)

_cell_formula_units_Z            8

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    ?

_cell_measurement_theta_min      1.71

_cell_measurement_theta_max      28.01

_exptl_crystal_description       rectangular

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.32

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.21

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.596

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    3.459

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.318

_exptl_absorpt_correction_T_max  0.484

_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_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  'Bruker Smart CCD Area Detector'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.3

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            17521

_diffrn_reflns_av_R_equivalents  0.0319

_diffrn_reflns_av_sigmaI/netI    0.0383

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       10

_diffrn_reflns_limit_l_min       -62

_diffrn_reflns_limit_l_max       60

_diffrn_reflns_theta_min         1.71

_diffrn_reflns_theta_max         28.01

_reflns_number_total             5061

_reflns_number_gt                3676

_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, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'

_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0153P)^2^+4.4473P] 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     SHELXL

_refine_ls_extinction_coef       0.021(4)

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_abs_structure_Flack   0.00(3)

_refine_ls_number_reflns         5061

_refine_ls_number_parameters     253

_refine_ls_number_restraints     1

_refine_ls_R_factor_all          0.0789

_refine_ls_R_factor_gt           0.0529

_refine_ls_wR_factor_ref         0.0993

_refine_ls_wR_factor_gt          0.0921

_refine_ls_goodness_of_fit_ref   1.149

_refine_ls_restrained_S_all      1.149

_refine_ls_shift/su_max          0.184

_refine_ls_shift/su_mean         0.015

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

Se1 Se 0.77483(10) 0.10150(15) 0.835464(14) 0.0496(3) Uani 1 1 d . . .
Se2 Se 0.07129(9) -0.10090(13) 0.666626(14) 0.0449(2) Uani 1 1 d . . .
O5 O 0.3394(16) 0.0938(8) 0.72142(12) 0.059(2) Uani 1 1 d . . .
O3 O 0.6777(16) 0.1232(9) 0.76154(13) 0.075(3) Uani 1 1 d . . .
H3 H 0.5698 0.1252 0.7502 0.113 Uiso 1 1 calc R . .
O1 O 0.397(2) 0.0133(14) 0.96509(14) 0.102(4) Uani 1 1 d . . .
C6 C 0.658(2) -0.0951(13) 0.89780(18) 0.059(3) Uani 1 1 d . . .
H6 H 0.7889 -0.1508 0.8909 0.071 Uiso 1 1 calc R . .
O4 O 0.4522(17) -0.0111(11) 0.53595(15) 0.072(2) Uani 1 1 d . . .
C8 C 0.5377(19) -0.0630(12) 0.84814(14) 0.061(3) Uani 1 1 d . . .
H8A H 0.3936 -0.0482 0.8377 0.073 Uiso 1 1 calc R . .
H8B H 0.5926 -0.1779 0.8454 0.073 Uiso 1 1 calc R . .
C15 C 0.3472(16) 0.0323(9) 0.62209(19) 0.041(2) Uani 1 1 d . . .
C10 C 0.651(2) -0.0109(11) 0.77911(18) 0.048(3) Uani 1 1 d . . .
C17 C 0.234(2) 0.0723(14) 0.5743(2) 0.061(3) Uani 1 1 d . . .
H17 H 0.1254 0.1131 0.5614 0.073 Uiso 1 1 calc R . .
O6 O 0.1654(15) -0.1243(10) 0.74014(14) 0.078(3) Uani 1 1 d . . .
H6A H 0.2822 -0.1220 0.7501 0.117 Uiso 1 1 calc R . .
C2 C 0.429(2) 0.0047(14) 0.9366(2) 0.056(3) Uani 1 1 d . . .
C19 C -0.005(2) 0.0112(14) 0.70206(16) 0.062(3) Uani 1 1 d . . .
H19A H -0.0291 0.1311 0.6988 0.075 Uiso 1 1 calc R . .
H19B H -0.1482 -0.0357 0.7095 0.075 Uiso 1 1 calc R . .
O2 O 0.4896(17) -0.1023(9) 0.78027(15) 0.069(3) Uani 1 1 d . . .
C4 C 0.3071(19) 0.0588(13) 0.88923(17) 0.052(3) Uani 1 1 d . . .
H4 H 0.2062 0.1092 0.8764 0.062 Uiso 1 1 calc R . .
C3 C 0.259(3) 0.0719(13) 0.91804(15) 0.054(3) Uani 1 1 d . . .
H3A H 0.1225 0.1220 0.9246 0.065 Uiso 1 1 calc R . .
C13 C 0.575(3) -0.0734(11) 0.58391(17) 0.054(2) Uani 1 1 d . . .
H13 H 0.7005 -0.1396 0.5781 0.064 Uiso 1 1 calc R . .
C14 C 0.541(2) -0.0470(11) 0.61185(17) 0.046(3) Uani 1 1 d . . .
H14 H 0.6532 -0.0845 0.6244 0.055 Uiso 1 1 calc R . .
C5 C 0.4994(17) -0.0266(13) 0.87943(16) 0.050(3) Uani 1 1 d . . .
C12 C 0.432(2) -0.0059(13) 0.56436(18) 0.047(3) Uani 1 1 d . . .
C9 C 0.8632(18) -0.0065(9) 0.80053(18) 0.043(2) Uani 1 1 d . . .
H9A H 0.9924 0.0548 0.7922 0.052 Uiso 1 1 calc R . .
H9B H 0.9149 -0.1212 0.8043 0.052 Uiso 1 1 calc R . .
C20 C 0.1790(17) -0.0110(10) 0.72201(18) 0.041(2) Uani 1 1 d . . .
C11 C 0.651(3) -0.0914(19) 0.5243(3) 0.114(6) Uani 1 1 d . . .
H11A H 0.6435 -0.0864 0.5042 0.171 Uiso 1 1 calc R . .
H11B H 0.6555 -0.2076 0.5302 0.171 Uiso 1 1 calc R . .
H11C H 0.7897 -0.0347 0.5307 0.171 Uiso 1 1 calc R . .
C16 C 0.1912(13) 0.0917(12) 0.6013(2) 0.052(3) Uani 1 1 d . . .
H16 H 0.0549 0.1460 0.6069 0.063 Uiso 1 1 calc R . .
C7 C 0.623(2) -0.0816(13) 0.92696(17) 0.047(3) Uani 1 1 d . . .
H7 H 0.7291 -0.1295 0.9395 0.057 Uiso 1 1 calc R . .
C18 C 0.310(2) 0.0530(11) 0.6524(2) 0.061(3) Uani 1 1 d . . .
H18A H 0.2637 0.1688 0.6562 0.073 Uiso 1 1 calc R . .
H18B H 0.4557 0.0320 0.6622 0.073 Uiso 1 1 calc R . .
C1 C 0.188(3) 0.088(2) 0.9752(2) 0.124(8) Uani 1 1 d . . .
H1A H 0.1878 0.0848 0.9953 0.186 Uiso 1 1 calc R . .
H1B H 0.0568 0.0253 0.9682 0.186 Uiso 1 1 calc R . .
H1C H 0.1789 0.2028 0.9689 0.186 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

Se1 0.0499(6) 0.0622(7) 0.0367(4) -0.0082(4) 0.0003(4) -0.0070(8)
Se2 0.0418(5) 0.0513(5) 0.0415(4) -0.0093(4) 0.0008(4) -0.0074(7)
O5 0.095(7) 0.047(4) 0.035(3) 0.005(3) -0.013(3) -0.031(4)
O3 0.102(7) 0.072(5) 0.053(3) 0.018(3) -0.017(4) -0.041(5)
O1 0.107(8) 0.168(10) 0.030(4) 0.005(5) -0.004(4) 0.019(8)
C6 0.080(8) 0.057(7) 0.040(4) -0.006(5) -0.005(4) 0.002(6)
O4 0.060(5) 0.096(6) 0.059(4) 0.007(4) 0.004(4) 0.003(5)
C8 0.055(7) 0.096(7) 0.030(3) -0.026(4) 0.004(4) -0.046(6)
C15 0.039(6) 0.018(4) 0.065(5) -0.003(4) 0.000(4) 0.006(4)
C10 0.085(8) 0.026(4) 0.033(4) 0.012(3) 0.014(4) 0.026(4)
C17 0.045(7) 0.067(8) 0.071(6) 0.014(5) -0.015(6) 0.008(7)
O6 0.063(6) 0.098(6) 0.074(4) 0.045(4) -0.014(3) -0.007(5)
C2 0.059(8) 0.060(8) 0.049(5) 0.009(5) -0.008(5) -0.001(6)
C19 0.057(7) 0.105(8) 0.024(3) -0.009(4) 0.008(4) 0.023(6)
O2 0.090(7) 0.050(4) 0.067(4) 0.018(4) -0.015(4) -0.026(4)
C4 0.028(6) 0.079(7) 0.048(4) 0.017(4) -0.007(4) 0.005(6)
C3 0.044(6) 0.078(7) 0.040(4) -0.001(4) 0.003(5) -0.001(7)
C13 0.034(5) 0.058(6) 0.069(5) 0.017(4) 0.009(6) 0.012(6)
C14 0.046(7) 0.048(5) 0.044(4) 0.010(4) -0.003(4) -0.010(5)
C5 0.043(6) 0.080(7) 0.025(3) 0.001(4) 0.001(3) -0.033(5)
C12 0.040(6) 0.063(7) 0.039(4) 0.004(5) -0.004(4) -0.004(5)
C9 0.050(6) 0.023(4) 0.056(4) 0.002(3) -0.006(4) 0.004(4)
C20 0.055(5) 0.033(4) 0.036(4) -0.011(4) -0.001(3) -0.024(4)
C11 0.077(12) 0.169(17) 0.096(9) -0.018(10) 0.029(8) -0.011(11)
C16 0.009(3) 0.054(6) 0.094(7) -0.007(6) -0.007(4) 0.007(4)
C7 0.040(6) 0.060(7) 0.042(4) 0.005(4) -0.017(4) 0.009(6)
C18 0.059(7) 0.044(5) 0.080(6) 0.011(4) 0.003(6) 0.010(5)
C1 0.102(14) 0.23(2) 0.042(6) 0.006(9) 0.025(6) 0.035(13)

_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

Se1 C9 1.938(8) . ?
Se1 C8 1.975(9) . ?
Se2 C18 1.953(11) . ?
Se2 C19 1.955(8) . ?
O5 C20 1.238(11) . ?
O3 C10 1.359(10) . ?
O3 H3 0.8200 . ?
O1 C2 1.369(13) . ?
O1 C1 1.417(18) . ?
C6 C5 1.373(13) . ?
C6 C7 1.407(11) . ?
C6 H6 0.9300 . ?
O4 C12 1.359(11) . ?
O4 C11 1.419(16) . ?
C8 C5 1.534(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C15 C14 1.364(14) . ?
C15 C16 1.413(12) . ?
C15 C18 1.467(12) . ?
C10 O2 1.174(13) . ?
C10 C9 1.589(14) . ?
C17 C16 1.321(12) . ?
C17 C12 1.377(17) . ?
C17 H17 0.9300 . ?
O6 C20 1.246(10) . ?
O6 H6A 0.8200 . ?
C2 C7 1.388(16) . ?
C2 C3 1.419(16) . ?
C19 C20 1.430(14) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C4 C5 1.374(15) . ?
C4 C3 1.404(12) . ?
C4 H4 0.9300 . ?
C3 H3A 0.9300 . ?
C13 C12 1.352(15) . ?
C13 C14 1.362(12) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C16 H16 0.9300 . ?
C7 H7 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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

C9 Se1 C8 98.8(4) . . ?
C18 Se2 C19 100.1(5) . . ?
C10 O3 H3 109.5 . . ?
C2 O1 C1 117.9(10) . . ?
C5 C6 C7 120.5(10) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C12 O4 C11 118.1(10) . . ?
C5 C8 Se1 105.8(5) . . ?
C5 C8 H8A 110.6 . . ?
Se1 C8 H8A 110.6 . . ?
C5 C8 H8B 110.6 . . ?
Se1 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C14 C15 C16 114.6(8) . . ?
C14 C15 C18 121.4(8) . . ?
C16 C15 C18 124.0(8) . . ?
O2 C10 O3 126.7(10) . . ?
O2 C10 C9 125.9(8) . . ?
O3 C10 C9 107.0(9) . . ?
C16 C17 C12 122.6(10) . . ?
C16 C17 H17 118.7 . . ?
C12 C17 H17 118.7 . . ?
C20 O6 H6A 109.5 . . ?
O1 C2 C7 117.4(10) . . ?
O1 C2 C3 120.6(12) . . ?
C7 C2 C3 121.9(9) . . ?
C20 C19 Se2 110.7(7) . . ?
C20 C19 H19A 109.5 . . ?
Se2 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
Se2 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C5 C4 C3 121.8(9) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C3 C2 116.6(12) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
C12 C13 C14 121.6(12) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 122.6(11) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C6 C5 C4 120.5(8) . . ?
C6 C5 C8 116.8(9) . . ?
C4 C5 C8 122.5(8) . . ?
C13 C12 O4 128.5(11) . . ?
C13 C12 C17 116.3(9) . . ?
O4 C12 C17 115.2(10) . . ?
C10 C9 Se1 111.2(6) . . ?
C10 C9 H9A 109.4 . . ?
Se1 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
Se1 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O5 C20 O6 122.9(9) . . ?
O5 C20 C19 116.8(9) . . ?
O6 C20 C19 120.2(9) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C16 C15 121.8(9) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C2 C7 C6 118.6(9) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C15 C18 Se2 112.0(7) . . ?
C15 C18 H18A 109.2 . . ?
Se2 C18 H18A 109.2 . . ?
C15 C18 H18B 109.2 . . ?
Se2 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        28.01

_diffrn_measured_fraction_theta_full 0.985

_refine_diff_density_max         0.487

_refine_diff_density_min         -0.679

_refine_diff_density_rms         0.088