# Supplementary Material (ESI) for Perkin Transactions

# This journal is © The Royal Society of Chemistry 1999

# CCDC Number: 207/357



data_CRYSTALS_cif

_audit_creation_date        99-09-01

_audit_creation_method      CRYSTALS

_publ_contact_author_name                       'Steve Davies'

_publ_contact_author_address

;

Dyson Perrins Laboratory

South Parks Road

OXFORD OX1 3QY

;

_publ_contact_author_phone                      ' 01865 275695 '

_publ_contact_author_email        'steve.davies@chem.ox.ac.uk '

## -----------------REFERENCES ----------------------##

_publ_section_references

;

 

Carruthers, J.R. and Watkin, D.J. (1979),

Acta Cryst, A35, 698-699.

 

Larsen, A. C. (1967), Acta Cryst. 23, 440-449.

 

 

North, A.C.T., Phillips, D.C. and Mathews, F.S., (1968), Acta Cryst, A24,

351-359.

 

Sheldrick, G.M. (1986).  SHELXS86. Program for the solution of

crystal structures.  Univ. of Gottingen, Federal Republic of Germany.

 

Walker, N., and Stuart, D. DIFABS. Acta Cryst, (1983) A39, 158-166.

 

Watkin, D.J., Prout, C.K. Carruthers, J.R. & Betteridge, P.W. (1996) CRYSTALS

Issue 10. Chemical Crystallography Laboratory, OXFORD, UK.

 

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

Crystallography Laboratory, OXFORD, UK.

 

Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical

Crystallography Laboratory, Oxford, UK.

;

#==========================================================================

# Diffractometer details

#==========================================================================

_diffrn_radiation_monochromator      graphite

# choose from:

#_diffrn_measurement_device     '  Enraf-Nonius CAD4 '

#_computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)'

_computing_data_reduction

;

RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994)

;

_computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)'



#==========================================================================

# General computing

#==========================================================================

_computing_structure_refinement

;

CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)

;

_computing_publication_material

;

CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)

;

_computing_molecular_graphics

;

CAMERON

;

# _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)'

 

#==========================================================================

_chemical_melting_point                    'not measured'

_refine_ls_matrix_type                   full

_atom_sites_solution_primary   Patterson

_atom_sites_solution_hydrogens       Geometric

_refine_ls_hydrogen_treatment

;

 noref

;

#****************************************************************************

_cell_length_a 11.639(4)

_cell_angle_alpha 90

_cell_length_b 6.617(4)

_cell_angle_beta  92.439(4)

_cell_length_c 13.030(8)

_cell_angle_gamma 90

_cell_volume  1002.66

_symmetry_cell_setting 'Monoclinic '

_symmetry_space_group_name_H-M 'P 1 21 1 '

loop_

 _symmetry_equiv_pos_as_xyz

 'x,y,z'

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

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

 'I   '   -0.7260    1.8120   20.1472    4.3470

   18.9949    0.3814    7.5138   27.7660    2.2735   66.8776    4.0712

'International_Tables_Vol_IV_Table_2.2B'

 'N   '    0.0040    0.0030   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   '    0.0080    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'

 'C   '    0.0020    0.0020    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'

_chemical_formula_sum

' C21 H24 I1 N1 O2 '

_chemical_formula_moiety

' C21 H24 I1 N1 O2 '

_chemical_compound_source

;

see paper

;

_chemical_formula_weight     449.331

_cell_measurement_reflns_used        25

_cell_measurement_theta_min        8

_cell_measurement_theta_max        13

_cell_measurement_temperature        298

_cell_formula_units_Z     2

_exptl_crystal_description ' plate '

_exptl_crystal_colour 'pale yellow '

_exptl_crystal_size_min 0.05

_exptl_crystal_size_mid 0.08

_exptl_crystal_size_max 0.22

_exptl_crystal_density_diffrn 1.49

_exptl_crystal_density_meas ?

_exptl_crystal_F_000 452

_exptl_absorpt_coefficient_mu 1.59

_exptl_absorpt_correction_type empirical

_diffrn_standards_interval_time 3600

_diffrn_standards_number 3

_diffrn_ambient_temperature          298

_diffrn_reflns_number 5214

_reflns_number_total 3515

_diffrn_reflns_av_R_equivalents 0.022

_reflns_number_observed 2756

_diffrn_reflns_theta_min 0.00

_diffrn_reflns_theta_max 25

_diffrn_reflns_limit_h_min -1

_diffrn_reflns_limit_h_max 13

_diffrn_reflns_limit_k_min -1

_diffrn_reflns_limit_k_max 7

_diffrn_reflns_limit_l_min -15

_diffrn_reflns_limit_l_max 15

_reflns_limit_h_min -13

_reflns_limit_h_max 13

_reflns_limit_k_min -7

_reflns_limit_k_max 7

_reflns_limit_l_min 0

_reflns_limit_l_max 15

_refine_diff_density_min -0.44

_refine_diff_density_max 0.61

_refine_ls_number_reflns 2756

_refine_ls_number_parameters 228

_refine_ls_R_factor_obs 0.0266

_refine_ls_wR_factor_obs 0.0293

_refine_ls_goodness_of_fit_obs 1.0983

_refine_ls_shift/esd_max 0.014182

_refine_ls_structure_factor_coef F

_diffrn_radiation_type       'Mo K\a'

_diffrn_radiation_wavelength      0.71073

_diffrn_measurement_method 2\q/\w

 

loop_

_atom_site_label

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_occupancy

_atom_site_thermal_displace_type

 I1 -0.88635(3) 0.0169(1) -0.01459(3) 0.0545 1.0000 Uani

 N1 -0.7908(3) 0.3094(5) -0.1979(2) 0.0310 1.0000 Uani

 O1 -0.5316(4) 0.6970(7) 0.0297(3) 0.0703 1.0000 Uani

 O2 -0.6461(3) 0.4792(8) 0.0982(2) 0.0564 1.0000 Uani

 C1 -0.6052(4) 0.5715(7) 0.0162(4) 0.0464 1.0000 Uani

 C2 -0.6586(3) 0.536(1) -0.0879(3) 0.0317 1.0000 Uani

 C3 -0.7215(3) 0.3260(5) -0.1019(3) 0.0291 1.0000 Uani

 C4 -0.7926(3) 0.2983(6) -0.0078(3) 0.0353 1.0000 Uani

 C5 -0.7168(4) 0.2985(8) 0.0904(4) 0.0474 1.0000 Uani

 C6 -0.7820(5) 0.299(1) 0.1894(4) 0.0626 1.0000 Uani

 C7 -0.8595(3) 0.4877(9) -0.2236(3) 0.0373 1.0000 Uani

 C8 -0.9605(4) 0.4478(7) -0.2979(3) 0.0401 1.0000 Uani

 C9 -1.0265(4) 0.2760(9) -0.2947(4) 0.0559 1.0000 Uani

 C10 -1.1203(5) 0.249(1) -0.3620(5) 0.0635 1.0000 Uani

 C11 -1.1497(5) 0.399(1) -0.4331(4) 0.0574 1.0000 Uani

 C12 -1.0843(5) 0.566(1) -0.4373(4) 0.0611 1.0000 Uani

 C13 -0.9897(4) 0.5929(8) -0.3703(4) 0.0542 1.0000 Uani

 C14 -0.7315(4) 0.2216(6) -0.2868(3) 0.0386 1.0000 Uani

 C15 -0.7004(5) 0.002(1) -0.2678(4) 0.0586 1.0000 Uani

 C16 -0.6316(4) 0.3436(6) -0.3258(3) 0.0377 1.0000 Uani

 C17 -0.5213(4) 0.3229(8) -0.2841(4) 0.0508 1.0000 Uani

 C18 -0.4318(5) 0.441(1) -0.3186(6) 0.0696 1.0000 Uani

 C19 -0.4521(6) 0.5767(9) -0.3955(6) 0.0745 1.0000 Uani

 C20 -0.5597(7) 0.5975(8) -0.4402(5) 0.0682 1.0000 Uani

 C21 -0.6495(4) 0.4826(9) -0.4042(4) 0.0542 1.0000 Uani

 H21 -0.7162 0.6452 -0.1027 0.0294 1.0000 Uiso

 H22 -0.5967 0.5432 -0.1387 0.0294 1.0000 Uiso

 H31 -0.6673 0.2106 -0.1104 0.0294 1.0000 Uiso

 H41 -0.8494 0.4113 -0.0047 0.0479 1.0000 Uiso

 H51 -0.6686 0.1742 0.0844 0.0479 1.0000 Uiso

 H61 -0.8336 0.1786 0.1908 0.0649 1.0000 Uiso

 H62 -0.8292 0.4252 0.1927 0.0649 1.0000 Uiso

 H63 -0.7259 0.2946 0.2497 0.0649 1.0000 Uiso

 H71 -0.8898 0.5433 -0.1587 0.0401 1.0000 Uiso

 H72 -0.8086 0.5902 -0.2550 0.0401 1.0000 Uiso

 H91 -1.0064 0.1689 -0.2428 0.0694 1.0000 Uiso

 H101 -1.1668 0.1223 -0.3596 0.0590 1.0000 Uiso

 H111 -1.2188 0.3822 -0.4806 0.0694 1.0000 Uiso

 H121 -1.1041 0.6721 -0.4897 0.0550 1.0000 Uiso

 H131 -0.9424 0.7186 -0.3745 0.0658 1.0000 Uiso

 H141 -0.7913 0.2295 -0.3441 0.0389 1.0000 Uiso

 H151 -0.6609 -0.0525 -0.3285 0.0600 1.0000 Uiso

 H152 -0.7720 -0.0773 -0.2571 0.0600 1.0000 Uiso

 H153 -0.6479 -0.0082 -0.2053 0.0600 1.0000 Uiso

 H171 -0.5055 0.2217 -0.2283 0.0759 1.0000 Uiso

 H181 -0.3525 0.4255 -0.2867 0.0511 1.0000 Uiso

 H191 -0.3877 0.6622 -0.4196 0.0773 1.0000 Uiso

 H201 -0.5737 0.6944 -0.4983 0.0567 1.0000 Uiso

 H211 -0.7288 0.5008 -0.4356 0.0773 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

 I1 0.0518(2) 0.0540(2) 0.0699(2) 0.0100(3) 0.0134(1) -0.0149(2)

 N1 0.033(2) 0.030(2) 0.032(2) -0.002(1) -0.005(1) -0.005(1)

 O1 0.080(3) 0.105(3) 0.071(3) -0.016(2) -0.017(2) -0.049(3)

 O2 0.064(2) 0.085(4) 0.038(2) -0.009(2) -0.010(1) -0.017(2)

 C1 0.037(2) 0.064(4) 0.050(3) -0.008(2) -0.009(2) -0.013(2)

 C2 0.036(2) 0.029(3) 0.039(2) -0.001(2) -0.005(1) -0.013(2)

 C3 0.029(2) 0.027(2) 0.032(2) 0.002(2) -0.003(2) 0.002(2)

 C4 0.028(2) 0.038(2) 0.041(2) 0.000(2) 0.003(2) 0.003(2)

 C5 0.046(3) 0.058(3) 0.041(3) 0.003(2) -0.001(2) 0.008(2)

 C6 0.067(4) 0.105(5) 0.039(3) 0.010(3) 0.011(3) 0.018(3)

 C7 0.037(2) 0.039(3) 0.038(2) 0.001(2) -0.007(1) -0.003(2)

 C8 0.033(2) 0.062(3) 0.031(2) 0.001(2) 0.000(2) -0.001(2)

 C9 0.050(3) 0.071(3) 0.057(3) 0.010(3) -0.014(2) -0.014(3)

 C10 0.048(3) 0.093(4) 0.075(4) -0.000(3) -0.017(3) -0.027(3)

 C11 0.035(3) 0.127(5) 0.046(3) -0.013(3) -0.009(3) 0.001(3)

 C12 0.057(3) 0.104(7) 0.048(3) 0.009(3) -0.019(3) 0.015(3)

 C13 0.050(3) 0.064(3) 0.051(3) 0.011(2) -0.000(2) 0.005(2)

 C14 0.046(3) 0.037(2) 0.035(2) -0.005(2) -0.003(2) -0.002(2)

 C15 0.090(3) 0.036(3) 0.067(3) 0.002(4) 0.021(2) 0.003(4)

 C16 0.044(2) 0.039(2) 0.032(2) -0.007(2) 0.002(2) 0.001(2)

 C17 0.049(3) 0.068(3) 0.040(3) -0.003(2) 0.006(2) 0.000(2)

 C18 0.052(3) 0.109(6) 0.077(4) -0.034(4) 0.021(3) -0.011(3)

 C19 0.087(5) 0.070(5) 0.101(5) -0.005(4) 0.049(4) -0.020(3)

 C20 0.118(6) 0.053(3) 0.074(4) 0.017(3) 0.047(4) 0.016(3)

 C21 0.073(3) 0.048(4) 0.052(3) 0.009(3) 0.016(2) 0.013(3)

_refine_ls_extinction_coef 0.9(30)

_refine_ls_extinction_method

    'Larson 1970 Crystallographic Computing eq 22'

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

N1 . C3 . 1.464(5)    yes

N1 . C7 . 1.456(6)    yes

N1 . C14 . 1.491(5)    yes

O1 . C1 . 1.201(5)    yes

O2 . C1 . 1.335(6)    yes

O2 . C5 . 1.453(7)    yes

C1 . C2 . 1.487(6)    yes

C2 . C3 . 1.575(7)    yes

C2 . H21 . 1.000(6)    no

C2 . H22 . 1.000(4)    no

C3 . C4 . 1.520(5)    yes

C3 . H31 . 1.000(4)    no

C4 . C5 . 1.523(6)    yes

C4 . H41 . 1.000(4)    no

C5 . C6 . 1.525(7)    yes

C5 . H51 . 1.000(5)    no

C6 . H61 . 1.000(7)    no

C6 . H62 . 1.000(6)    no

C6 . H63 . 1.000(6)    no

C7 . C8 . 1.514(6)    yes

C7 . H71 . 1.000(4)    no

C7 . H72 . 1.000(5)    no

C8 . C9 . 1.374(7)    yes

C8 . C13 . 1.378(6)    yes

C9 . C10 . 1.383(8)    yes

C9 . H91 . 1.000(5)    no

C10 . C11 . 1.386(9)    yes

C10 . H101 . 1.000(6)    no

C11 . C12 . 1.346(9)    yes

C11 . H111 . 1.000(5)    no

C12 . C13 . 1.388(8)    yes

C12 . H121 . 1.000(6)    no

C13 . H131 . 1.000(5)    no

C14 . C15 . 1.514(9)    yes

C14 . C16 . 1.521(6)    yes

C14 . H141 . 1.000(4)    no

C15 . H151 . 1.000(5)    no

C15 . H152 . 1.000(6)    no

C15 . H153 . 1.000(5)    no

C16 . C17 . 1.379(7)    yes

C16 . C21 . 1.383(7)    yes

C17 . C18 . 1.391(8)    yes

C17 . H171 . 1.000(5)    no

C18 . C19 . 1.361(9)    yes

C18 . H181 . 1.000(7)    no

C19 . C20 . 1.36(1)    yes

C19 . H191 . 1.000(6)    no

C20 . C21 . 1.391(8)    yes

C20 . H201 . 1.000(6)    no

C21 . H211 . 1.000(5)    no

H21 . H22 . 1.63    no

H61 . H62 . 1.63    no

H61 . H63 . 1.63    no

H62 . H63 . 1.63    no

H71 . H72 . 1.63    no

H151 . H152 . 1.63    no

H151 . H153 . 1.63    no

H152 . H153 . 1.63    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

C3 . N1 . C7 . 114.4(3)    no

C3 . N1 . C14 . 115.9(3)    no

C7 . N1 . C14 . 113.9(3)    no

C1 . O2 . C5 . 122.7(3)    no

O1 . C1 . O2 . 118.4(5)    no

O1 . C1 . C2 . 120.7(5)    no

O2 . C1 . C2 . 120.5(4)    no

C1 . C2 . C3 . 114.8(4)    no

C1 . C2 . H21 . 108.1(5)    no

C3 . C2 . H21 . 108.1(3)    no

C1 . C2 . H22 . 108.1(3)    no

C3 . C2 . H22 . 108.1(5)    no

H21 . C2 . H22 . 109.4(5)    no

N1 . C3 . C2 . 113.7(3)    no

N1 . C3 . C4 . 112.4(3)    no

C2 . C3 . C4 . 106.2(3)    no

N1 . C3 . H31 . 100.1(3)    no

C2 . C3 . H31 . 113.2(3)    no

C4 . C3 . H31 . 111.4(3)    no

C3 . C4 . C5 . 111.2(3)    no

C3 . C4 . H41 . 109.0(3)    no

C5 . C4 . H41 . 109.0(4)    no

O2 . C5 . C4 . 111.5(4)    no

O2 . C5 . C6 . 103.8(4)    no

C4 . C5 . C6 . 114.8(4)    no

O2 . C5 . H51 . 111.4(4)    no

C4 . C5 . H51 . 103.9(4)    no

C6 . C5 . H51 . 111.7(4)    no

C5 . C6 . H61 . 109.5(5)    no

C5 . C6 . H62 . 109.5(5)    no

H61 . C6 . H62 . 109.5(5)    no

C5 . C6 . H63 . 109.4(5)    no

H61 . C6 . H63 . 109.5(6)    no

H62 . C6 . H63 . 109.5(6)    no

N1 . C7 . C8 . 114.2(4)    no

N1 . C7 . H71 . 108.3(4)    no

C8 . C7 . H71 . 108.3(3)    no

N1 . C7 . H72 . 108.3(3)    no

C8 . C7 . H72 . 108.3(4)    no

H71 . C7 . H72 . 109.5(5)    no

C7 . C8 . C9 . 123.0(4)    no

C7 . C8 . C13 . 118.6(4)    no

C9 . C8 . C13 . 118.4(4)    no

C8 . C9 . C10 . 120.9(5)    no

C8 . C9 . H91 . 119.5(5)    no

C10 . C9 . H91 . 119.5(5)    no

C9 . C10 . C11 . 119.9(5)    no

C9 . C10 . H101 . 120.1(6)    no

C11 . C10 . H101 . 120.1(5)    no

C10 . C11 . C12 . 119.3(5)    no

C10 . C11 . H111 . 120.3(7)    no

C12 . C11 . H111 . 120.3(7)    no

C11 . C12 . C13 . 121.0(6)    no

C11 . C12 . H121 . 119.5(6)    no

C13 . C12 . H121 . 119.5(6)    no

C8 . C13 . C12 . 120.4(5)    no

C8 . C13 . H131 . 119.8(5)    no

C12 . C13 . H131 . 119.8(5)    no

N1 . C14 . C15 . 111.2(4)    no

N1 . C14 . C16 . 116.0(3)    no

C15 . C14 . C16 . 112.5(4)    no

N1 . C14 . H141 . 103.3(4)    no

C15 . C14 . H141 . 109.0(4)    no

C16 . C14 . H141 . 103.9(4)    no

C14 . C15 . H151 . 109.5(5)    no

C14 . C15 . H152 . 109.5(5)    no

H151 . C15 . H152 . 109.5(7)    no

C14 . C15 . H153 . 109.5(6)    no

H151 . C15 . H153 . 109.5(5)    no

H152 . C15 . H153 . 109.5(6)    no

C14 . C16 . C17 . 121.9(4)    no

C14 . C16 . C21 . 120.4(4)    no

C17 . C16 . C21 . 117.7(4)    no

C16 . C17 . C18 . 121.0(5)    no

C16 . C17 . H171 . 119.5(5)    no

C18 . C17 . H171 . 119.5(6)    no

C17 . C18 . C19 . 119.9(6)    no

C17 . C18 . H181 . 120.0(8)    no

C19 . C18 . H181 . 120.0(7)    no

C18 . C19 . C20 . 120.6(6)    no

C18 . C19 . H191 . 119.7(8)    no

C20 . C19 . H191 . 119.7(8)    no

C19 . C20 . C21 . 119.4(6)    no

C19 . C20 . H201 . 120.3(7)    no

C21 . C20 . H201 . 120.3(8)    no

C16 . C21 . C20 . 121.4(5)    no

C16 . C21 . H211 . 119.3(5)    no

C20 . C21 . H211 . 119.3(6)    no

C2 . H21 . H22 . 35.3(2)    no

C2 . H22 . H21 . 35.3(3)    no

C6 . H61 . H62 . 35.2(3)    no

C6 . H61 . H63 . 35.3(3)    no

H62 . H61 . H63 . 60.00    no

C6 . H62 . H61 . 35.3(4)    no

C6 . H62 . H63 . 35.3(3)    no

H61 . H62 . H63 . 60.00    no

C6 . H63 . H61 . 35.3(4)    no

C6 . H63 . H62 . 35.3(4)    no

H61 . H63 . H62 . 60.00    no

C7 . H71 . H72 . 35.3(3)    no

C7 . H72 . H71 . 35.3(3)    no

C15 . H151 . H152 . 35.3(4)    no

C15 . H151 . H153 . 35.2(3)    no

H152 . H151 . H153 . 60.00    no

C15 . H152 . H151 . 35.3(4)    no

C15 . H152 . H153 . 35.2(3)    no

H151 . H152 . H153 . 60.00    no

C15 . H153 . H151 . 35.3(3)    no

C15 . H153 . H152 . 35.3(4)    no

H151 . H153 . H152 . 60.00    no