# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

_database_code_CSD	195978


_audit_creation_method 'maXus + CRYSTALS_ver_12-03-99'
_audit_creation_date        02-09-10


_journal_coden_Cambridge     ?


loop_
_publ_author_name
'Martin Banwell'
'Alison J. Edwards'
'Ernest Hamel'
'Katrina A. Joliffe'
'Jason A. Smith'
'Pascal Verdier-Pinard'

_publ_contact_author_name     	'Prof Martin Banwell'  
_publ_contact_author_address 
;
Research School of Chemistry
Australian National University
Science Road
ACTON
ACT
2601
AUSTRALIA
;

_publ_contact_author_email       'MGB@RSC.ANU.EDU.AU'

_publ_requested_journal       
'Organic & Biomolecular Chemistry'


_publ_section_title		
;
Total synthesis of (±)-rhazinal, an alkaloidal spindle 
toxin from Kopsia teoi
;

_publ_section_abstract
;
The only crystals ever obtained after exhaustive
attempts at crystal growth were very fine needles.  
The largest available had dimensions 35 x 45 x 135 
m and was used in this experiment.  
No diffraction was observable above T
;

_publ_section_exptl_refinement
;
The limited data set arising from the low limit of diffraction 
necessitated the use of a predominantly isotropic model in 
this refinement.
;

_chemical_compound_source        'Local laboratory'
_exptl_crystal_description       'needle'
_exptl_crystal_colour            'Colourless'
_cell_measurement_temperature     200
_refine_ls_hydrogen_treatment    'noref'


_diffrn_measurement_device  'KappaCCD'
_computing_data_collection 'COLLECT (Nonius, 2001)'
_computing_data_reduction  
'Denzo and Scalepak (Otwinowski & Minor, 1997)'

_diffrn_radiation_source  'fine-focus sealed tube'
_diffrn_reflns_limit_h_min    -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min    -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min    -11
_diffrn_reflns_limit_l_max     11

loop_
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id all


_diffrn_orient_matrix_type 'X=UH'
_diffrn_orient_matrix_UB_11    0.08976
_diffrn_orient_matrix_UB_12    0.01575
_diffrn_orient_matrix_UB_13    0.02211
_diffrn_orient_matrix_UB_21   -0.00899
_diffrn_orient_matrix_UB_22    0.01335
_diffrn_orient_matrix_UB_23    0.08239
_diffrn_orient_matrix_UB_31    0.01699
_diffrn_orient_matrix_UB_32   -0.07612
_diffrn_orient_matrix_UB_33    0.01902

_cell_formula_units_Z     4
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method  'not measured'
_exptl_special_details
;
?
;
_chemical_formula_weight    322.408
_diffrn_radiation_type    ' MoK\a'

loop_
_symmetry_equiv_pos_as_xyz
'+X,+Y,+Z'
'-X,-Y,-Z'
'-X+ 1/2,+Y+ 1/2,-Z+ 1/2'
'+X+ 1/2,-Y+ 1/2,+Z+ 1/2'

_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_cell_setting 'Monoclinic'
_chemical_formula_moiety 'C20 H22 N2 O2 '
_chemical_formula_sum    'C20 H22 N2 O2 '
_chemical_name_systematic
;
?
;
_cell_length_a           11.1081(3)
_cell_length_b           12.6796(4)
_cell_length_c           11.6659(4)
_cell_angle_alpha                90.00
_cell_angle_beta          101.2591(13)
_cell_angle_gamma                90.00
_cell_volume             1611.48(9)
_diffrn_reflns_number  18571
_diffrn_reflns_theta_max  19.98
_cell_measurement_reflns_used     12226
_cell_measurement_theta_min        2.910
_cell_measurement_theta_max        19.980
_diffrn_measurement_method       'CCD'
_computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)'
# Absorption correction
_exptl_crystal_size_min 0.035 
_exptl_crystal_size_mid 0.045 
_exptl_crystal_size_max 0.13 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0    1    0  0.020
0   -1    0  0.015
1    0   -1  0.005
-1    0    1  0.040
1    0    1  0.080
-2    0    1  0.050


_exptl_absorpt_correction_type 'integration'
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_diffrn_reflns_av_R_equivalents   0.077
_exptl_absorpt_coefficient_mu     0.086
_exptl_crystal_F_000      688

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
'C   '    0.0033    0.0016    2.3100   20.8439
1.0200   10.2075    1.5886    0.5687    0.8650   51.6512    0.2156
'International_Tables_Vol_IV_Table_2.2B'
'H   '    0.0000    0.0000    0.4930   10.5109
0.3229   26.1257    0.1402    3.1424    0.0408   57.7997    0.0030
'International_Tables_Vol_IV_Table_2.2B'
'N   '    0.0061    0.0033   12.2126    0.0057
3.1322    9.8933    2.0125   28.9975    1.1663    0.5826  -11.5290
'International_Tables_Vol_IV_Table_2.2B'
'O   '    0.0106    0.0060    3.0485   13.2771
2.2868    5.7011    1.5463    0.3239    0.8670   32.9089    0.2508
'International_Tables_Vol_IV_Table_2.2B'
_atom_sites_solution_primary                direct                              
_atom_sites_solution_secondary            difmap
_atom_sites_solution_hydrogens 'geom difmap'

# Refinement statistics
_reflns_d_resolution_low    1.78
_reflns_d_resolution_high    0.72
_reflns_limit_h_min -10 
_reflns_limit_h_max 10 
_reflns_limit_k_min 0 
_reflns_limit_k_max 12 
_reflns_limit_l_min 0 
_reflns_limit_l_max 11 
_reflns_number_total 1493 
_refine_ls_matrix_type  full
_refine_ls_structure_factor_coef F 
_diffrn_measured_fraction_theta_max 0.996 
_reflns_number_gt 902 
_reflns_threshold_expression  >3.00\s(I)
_refine_ls_number_reflns 902 
_refine_ls_number_parameters 117 
_refine_ls_R_factor_gt 0.0973 
_refine_ls_wR_factor_ref 0.0854 
_refine_ls_goodness_of_fit_ref 0.8346 
_refine_ls_shift/su_max 0.000056 
_refine_ls_extinction_method 
'None'
_refine_diff_density_min -0.65 
_refine_diff_density_max 0.59 
_refine_diff_density_rms       0.28
_refine_ls_weighting_scheme calc 
_refine_ls_weighting_details 
;
Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 
1.20    0.175E-010.530    
;
_computing_structure_solution
;
SIR97 (Altomare et al, 1999)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al 2001)
;
_computing_publication_material
;
CRYSTALS (Watkin et al 2001) + maXus(Mackay et al., 1999)
;
_computing_molecular_graphics
;
CAMERON (Watkin et al 1996)
;

_publ_section_references
;
Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K.
(1999). maXus  Computer Program for the Solution and Refinement of
Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan
& The University of Glasgow.

Carruthers, J.R. and Watkin, D.J. (1979),
Acta Cryst, A35, 698-699

Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276,
edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326,
New York:Academic Press.

Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R.
(1999). J. Appl. Cryst. 32, 115-119.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON,
Chemical
Crystallography Laboratory, OXFORD, UK.

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. &
Cooper  R.I. (2001) CRYSTALS
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK.


Coppens, P. (1970). In Crystallographic Computing, edited by
F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard.

Nonius (2001).  COLLECT. Nonius BV, Delft, The Netherlands.
;

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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_occupancy
_atom_site_adp_type
O1 o 0.5736(5) 1.0084(4) 0.3794(4) 0.0466 1.0000 Uani 
C15 c 0.6289(7) 0.5489(7) 0.4527(7) 0.0423 1.0000 Uani 
O16 o 0.7076(5) 0.4875(5) 0.4317(5) 0.0523 1.0000 Uani 
C24 c 0.3309(8) 0.6795(7) -0.0272(8) 0.0526 1.0000 Uani 
C2 c 0.4770(7) 0.9768(6) 0.3189(7) 0.038(2) 1.0000 Uiso 
N3 n 0.3802(5) 0.9510(5) 0.3703(5) 0.0346(17) 1.0000 Uiso 
C4 c 0.2759(6) 0.8931(6) 0.3143(6) 0.0304(19) 1.0000 Uiso 
C5 c 0.1584(7) 0.9365(7) 0.3027(7) 0.040(2) 1.0000 Uiso 
C6 c 0.0556(7) 0.8813(6) 0.2531(6) 0.038(2) 1.0000 Uiso 
C7 c 0.0670(7) 0.7799(7) 0.2145(7) 0.040(2) 1.0000 Uiso 
C8 c 0.1828(7) 0.7359(6) 0.2240(6) 0.037(2) 1.0000 Uiso 
C9 c 0.2880(6) 0.7906(6) 0.2739(6) 0.0325(19) 1.0000 Uiso 
C10 c 0.4093(7) 0.7362(6) 0.2930(7) 0.035(2) 1.0000 Uiso 
C11 c 0.4950(6) 0.7291(6) 0.2189(6) 0.033(2) 1.0000 Uiso 
N12 n 0.5869(5) 0.6593(5) 0.2707(5) 0.0344(16) 1.0000 Uiso 
C13 c 0.5606(7) 0.6263(6) 0.3761(7) 0.035(2) 1.0000 Uiso 
C14 c 0.4518(6) 0.6737(6) 0.3897(7) 0.035(2) 1.0000 Uiso 
C17 c 0.6928(7) 0.6288(6) 0.2223(7) 0.035(2) 1.0000 Uiso 
C18 c 0.7196(8) 0.7100(7) 0.1358(7) 0.049(2) 1.0000 Uiso 
C19 c 0.6047(7) 0.7366(7) 0.0501(7) 0.044(2) 1.0000 Uiso 
C20 c 0.5043(6) 0.7889(6) 0.1091(6) 0.0304(19) 1.0000 Uiso 
C21 c 0.5446(7) 0.9034(6) 0.1379(7) 0.037(2) 1.0000 Uiso 
C22 c 0.4581(7) 0.9765(6) 0.1893(6) 0.039(2) 1.0000 Uiso 
C23 c 0.3816(7) 0.7881(6) 0.0215(7) 0.041(2) 1.0000 Uiso 
H31 h 0.4129(5) 0.9500(5) 0.4539(5) 0.0084(17) 1.0000 Uiso 
H151 h 0.6083(7) 0.5420(7) 0.5320(7) 0.0482 1.0000 Uiso 
H241 h 0.2517(8) 0.6918(7) -0.0832(8) 0.0603 1.0000 Uiso 
H242 h 0.3913(8) 0.6462(7) -0.0693(8) 0.0603 1.0000 Uiso 
H243 h 0.3163(8) 0.6317(7) 0.0369(8) 0.0603 1.0000 Uiso 
H51 h 0.1479(7) 1.0080(7) 0.3358(7) 0.040(2) 1.0000 Uiso 
H61 h -0.0270(7) 0.9154(6) 0.2425(6) 0.038(2) 1.0000 Uiso 
H71 h -0.0076(7) 0.7379(7) 0.1805(7) 0.040(2) 1.0000 Uiso 
H81 h 0.1913(7) 0.6643(6) 0.1906(6) 0.037(2) 1.0000 Uiso 
H141 h 0.4112(6) 0.6661(6) 0.4587(7) 0.035(2) 1.0000 Uiso 
H171 h 0.6720(7) 0.5611(6) 0.1790(7) 0.035(2) 1.0000 Uiso 
H172 h 0.7654(7) 0.6178(6) 0.2868(7) 0.035(2) 1.0000 Uiso 
H181 h 0.7861(8) 0.6853(7) 0.0956(7) 0.049(2) 1.0000 Uiso 
H182 h 0.7472(8) 0.7750(7) 0.1820(7) 0.049(2) 1.0000 Uiso 
H191 h 0.5732(7) 0.6709(7) 0.0070(7) 0.044(2) 1.0000 Uiso 
H192 h 0.6259(7) 0.7895(7) -0.0063(7) 0.044(2) 1.0000 Uiso 
H211 h 0.5588(7) 0.9357(6) 0.0635(7) 0.037(2) 1.0000 Uiso 
H212 h 0.6239(7) 0.9007(6) 0.1958(7) 0.037(2) 1.0000 Uiso 
H231 h 0.3932(7) 0.8342(6) -0.0451(7) 0.041(2) 1.0000 Uiso 
H232 h 0.3181(7) 0.8198(6) 0.0611(7) 0.041(2) 1.0000 Uiso 
H221 h 0.3718(7) 0.9527(6) 0.1592(6) 0.039(2) 1.0000 Uiso 
H222 h 0.4689(7) 1.0498(6) 0.1614(6) 0.039(2) 1.0000 Uiso 

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
O1 0.041(3) 0.054(4) 0.047(3) -0.011(3) 0.016(3) -0.010(3) 
C15 0.041(5) 0.034(5) 0.053(6) 0.003(4) 0.014(4) -0.001(5) 
O16 0.051(4) 0.037(4) 0.069(4) 0.004(3) 0.013(3) 0.011(3) 
C24 0.054(5) 0.044(6) 0.060(6) -0.003(5) 0.011(5) 0.002(5) 

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.230(8)    yes
C15 . O16 . 1.230(9)    yes
C15 . C13 . 1.439(11)    yes
C15 . H151 . 1.000    no
C24 . C23 . 1.552(12)    yes
C24 . H241 . 1.000    no
C24 . H242 . 1.000    no
C24 . H243 . 1.000    no
C2 . N3 . 1.370(9)    yes
C2 . C22 . 1.485(11)    yes
N3 . C4 . 1.419(9)    yes
N3 . H31 . 0.972    no
C4 . C5 . 1.40(1)    yes
C4 . C9 . 1.398(11)    yes
C5 . C6 . 1.37(1)    yes
C5 . H51 . 1.000    no
C6 . C7 . 1.376(11)    yes
C6 . H61 . 1.000    no
C7 . C8 . 1.386(11)    yes
C7 . H71 . 1.000    no
C8 . C9 . 1.39(1)    yes
C8 . H81 . 1.000    no
C9 . C10 . 1.49(1)    yes
C10 . C11 . 1.41(1)    yes
C10 . C14 . 1.38(1)    yes
C11 . N12 . 1.396(9)    yes
C11 . C20 . 1.51(1)    yes
N12 . C13 . 1.384(9)    yes
N12 . C17 . 1.45(1)    yes
C13 . C14 . 1.39(1)    yes
C14 . H141 . 1.000    no
C17 . C18 . 1.511(11)    yes
C17 . H171 . 1.000    no
C17 . H172 . 1.000    no
C18 . C19 . 1.498(11)    yes
C18 . H181 . 1.000    no
C18 . H182 . 1.000    no
C19 . C20 . 1.568(11)    yes
C19 . H191 . 1.000    no
C19 . H192 . 1.000    no
C20 . C21 . 1.54(1)    yes
C20 . C23 . 1.54(1)    yes
C21 . C22 . 1.539(11)    yes
C21 . H211 . 1.000    no
C21 . H212 . 1.000    no
C22 . H221 . 1.000    no
C22 . H222 . 1.000    no
C23 . H231 . 1.000    no
C23 . H232 . 1.000    no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O16 . C15 . C13 . 128.1(8)    yes
O16 . C15 . H151 . 115.4(5)    no
C13 . C15 . H151 . 116.4(5)    no
C23 . C24 . H241 . 108.1(4)    no
C23 . C24 . H242 . 108.9(5)    no
H241 . C24 . H242 . 109.475    no
C23 . C24 . H243 . 111.4(5)    no
H241 . C24 . H243 . 109.475    no
H242 . C24 . H243 . 109.476    no
O1 . C2 . N3 . 119.8(7)    yes
O1 . C2 . C22 . 121.3(7)    yes
N3 . C2 . C22 . 118.5(7)    yes
C2 . N3 . C4 . 124.3(6)    yes
C2 . N3 . H31 . 105.7(4)    no
C4 . N3 . H31 . 124.6(4)    no
N3 . C4 . C5 . 120.2(7)    yes
N3 . C4 . C9 . 120.8(6)    yes
C5 . C4 . C9 . 118.9(7)    yes
C4 . C5 . C6 . 121.7(8)    yes
C4 . C5 . H51 . 119.7(4)    no
C6 . C5 . H51 . 118.5(5)    no
C5 . C6 . C7 . 119.6(8)    yes
C5 . C6 . H61 . 120.0(5)    no
C7 . C6 . H61 . 120.3(5)    no
C6 . C7 . C8 . 119.5(8)    yes
C6 . C7 . H71 . 120.3(5)    no
C8 . C7 . H71 . 120.1(5)    no
C7 . C8 . C9 . 121.7(7)    yes
C7 . C8 . H81 . 119.4(5)    no
C9 . C8 . H81 . 118.8(4)    no
C4 . C9 . C8 . 118.5(7)    yes
C4 . C9 . C10 . 121.5(6)    yes
C8 . C9 . C10 . 119.7(7)    yes
C9 . C10 . C11 . 129.5(7)    yes
C9 . C10 . C14 . 122.8(7)    yes
C11 . C10 . C14 . 107.5(6)    yes
C10 . C11 . N12 . 107.4(6)    yes
C10 . C11 . C20 . 131.0(7)    yes
N12 . C11 . C20 . 121.4(6)    yes
C11 . N12 . C13 . 108.2(6)    yes
C11 . N12 . C17 . 125.4(6)    yes
C13 . N12 . C17 . 126.4(6)    yes
C15 . C13 . N12 . 125.5(7)    yes
C15 . C13 . C14 . 126.2(7)    yes
N12 . C13 . C14 . 108.1(6)    yes
C10 . C14 . C13 . 108.7(7)    yes
C10 . C14 . H141 . 125.1(4)    no
C13 . C14 . H141 . 126.1(4)    no
N12 . C17 . C18 . 111.0(6)    yes
N12 . C17 . H171 . 107.5(4)    no
C18 . C17 . H171 . 107.7(4)    no
N12 . C17 . H172 . 109.8(4)    no
C18 . C17 . H172 . 111.3(4)    no
H171 . C17 . H172 . 109.467    no
C17 . C18 . C19 . 110.2(7)    yes
C17 . C18 . H181 . 111.1(4)    no
C19 . C18 . H181 . 111.6(5)    no
C17 . C18 . H182 . 106.4(4)    no
C19 . C18 . H182 . 107.8(5)    no
H181 . C18 . H182 . 109.467    no
C18 . C19 . C20 . 112.8(7)    yes
C18 . C19 . H191 . 108.4(5)    no
C20 . C19 . H191 . 111.3(4)    no
C18 . C19 . H192 . 108.1(5)    no
C20 . C19 . H192 . 106.5(4)    no
H191 . C19 . H192 . 109.466    no
C11 . C20 . C19 . 109.4(6)    yes
C11 . C20 . C21 . 110.7(6)    yes
C19 . C20 . C21 . 107.1(6)    yes
C11 . C20 . C23 . 111.3(6)    yes
C19 . C20 . C23 . 108.7(6)    yes
C21 . C20 . C23 . 109.6(6)    yes
C20 . C21 . C22 . 118.4(6)    yes
C20 . C21 . H211 . 106.5(4)    no
C22 . C21 . H211 . 108.0(4)    no
C20 . C21 . H212 . 107.2(4)    no
C22 . C21 . H212 . 107.0(4)    no
H211 . C21 . H212 . 109.467    no
C2 . C22 . C21 . 115.0(6)    yes
C2 . C22 . H221 . 107.1(4)    no
C21 . C22 . H221 . 108.1(4)    no
C2 . C22 . H222 . 109.1(5)    no
C21 . C22 . H222 . 108.0(4)    no
H221 . C22 . H222 . 109.467    no
C24 . C23 . C20 . 117.5(7)    yes
C24 . C23 . H231 . 109.1(5)    no
C20 . C23 . H231 . 106.3(4)    no
C24 . C23 . H232 . 106.7(5)    no
C20 . C23 . H232 . 107.6(4)    no
H231 . C23 . H232 . 109.467    no