# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'A. Jalila Simaan'
_publ_contact_author_address     
;
Laboratoire de Bioinorganique Structurale
Universite Paul Cezanne Aix-Marseille III
Case 432
Faculte des Sciences et Techniques
Av Escadrille Normandie Niemen
Marseille
13397 cedex 20
FRANCE
;

_publ_contact_author_email       JALILA.SIMAAN@UNIV.U-3MRS.FR

_publ_section_title              
;
ACC-Oxidase like activity of a copper(II)-ACC complex in the
presence of hydrogen peroxide. Detection of a reaction intermediate at low
temperature.
;
loop_
_publ_author_name
'Jalila Simaan'
'Christian Gaudin'
'Wadih Ghattas'
'Michel Giorgi'
'Marius Reglier'
'Antal Rockenbauer'

# Attachment 'Structure-simaan.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 288376'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl Cu N3 O7'
_chemical_formula_weight         437.295

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.0940(1)
_cell_length_b                   19.5096(3)
_cell_length_c                   7.5502(2)
_cell_angle_alpha                90.
_cell_angle_beta                 102.8066(7)
_cell_angle_gamma                90.
_cell_volume                     1737.14(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15442
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    1.454
_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  KappaCCD
_diffrn_measurement_method       'Phi + omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15442
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3586
_reflns_number_gt                3265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD (Bruker-Nonius, 1998)'
_computing_cell_refinement       
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_publ_section_references         
;
Altamore, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C.,
Polidori, G. and Camalli, M. J. Appl. Cryst. (1994) 27, 435-436

Bruker-Nonius (1998). Kappa CCD Reference Manual. Nonius B.V., P.O.
Box 811, 2600
Av, Delft, The Netherlands.

Otwinowski, Z. and Minor, W. " Processing of X-ray Diffraction Data Collected
in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular
Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R.M. Sweet, Eds.,
Academic Press.

Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal
structures. Univ. of Gottingen, Germany.
;

_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^)+(0.0465P)^2^+2.5576P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     244
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.065

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
Cu1 Cu 0.80037(3) 0.053452(17) 0.77054(5) 0.03722(14) Uani 1 1 d . . .
Cl1 Cl 0.64666(6) 0.01809(4) 0.29182(11) 0.0446(2) Uani 1 1 d D . .
O1 O 0.9050(2) -0.13603(12) 0.8613(4) 0.0624(7) Uani 1 1 d . . .
O2 O 0.89616(18) -0.02585(11) 0.7992(4) 0.0485(6) Uani 1 1 d . . .
O3 O 0.6058(3) 0.05013(19) 0.1211(4) 0.0839(10) Uani 1 1 d . A .
O4 O 0.5805(4) 0.0502(3) 0.4097(7) 0.0644(13) Uiso 0.60 1 d PD A 1
O5 O 0.6195(6) -0.0535(3) 0.2798(9) 0.0851(17) Uiso 0.60 1 d PD A 1
O6 O 0.7641(4) 0.0253(3) 0.3728(7) 0.0648(14) Uiso 0.60 1 d PD A 1
O7 O 0.5943(11) -0.0380(6) 0.357(2) 0.070(4) Uiso 0.20 1 d PD A 2
O8 O 0.7577(8) -0.0026(6) 0.2646(19) 0.061(3) Uiso 0.20 1 d PD A 2
O9 O 0.6622(14) 0.0739(6) 0.417(2) 0.090(5) Uiso 0.20 1 d PD A 2
O10 O 0.5682(7) 0.0153(6) 0.4062(13) 0.040(2) Uiso 0.20 1 d PD A 3
O11 O 0.6672(15) -0.0472(6) 0.226(3) 0.103(7) Uiso 0.20 1 d PD A 3
O12 O 0.7473(8) 0.0542(6) 0.3763(15) 0.044(3) Uiso 0.20 1 d PD A 3
O13 O 0.86417(19) 0.09408(13) 1.0794(3) 0.0512(6) Uani 1 1 d . . .
H13A H 0.8437 0.0656 1.1537 0.061 Uiso 1 1 d R . .
H13B H 0.9399 0.0895 1.1051 0.061 Uiso 1 1 d R . .
N1 N 0.6775(2) -0.01271(12) 0.7938(3) 0.0339(5) Uani 1 1 d . . .
H1A H 0.6208 -0.0094 0.6884 0.041 Uiso 1 1 d R . .
H1B H 0.6539 0.0009 0.9010 0.041 Uiso 1 1 d R . .
N2 N 0.9168(2) 0.11258(13) 0.6992(4) 0.0374(6) Uani 1 1 d . . .
N3 N 0.7123(2) 0.14173(13) 0.7350(4) 0.0378(6) Uani 1 1 d . . .
C1 C 0.8514(3) -0.08283(15) 0.8272(4) 0.0392(7) Uani 1 1 d . . .
C2 C 0.7258(3) -0.08195(15) 0.8115(4) 0.0353(6) Uani 1 1 d . . .
C3 C 0.6742(3) -0.13573(19) 0.9096(6) 0.0599(10) Uani 1 1 d . . .
H3A H 0.7194 -0.1645 0.9821 0.072 Uiso 1 1 d R . .
H3B H 0.6038 -0.1213 0.9618 0.072 Uiso 1 1 d R . .
C4 C 0.6592(4) -0.14032(19) 0.7096(6) 0.0614(10) Uani 1 1 d . . .
H4A H 0.7056 -0.1758 0.6546 0.074 Uiso 1 1 d R . .
H4B H 0.5868 -0.1268 0.6353 0.074 Uiso 1 1 d R . .
C5 C 1.0170(3) 0.09167(17) 0.6728(5) 0.0484(8) Uani 1 1 d . . .
H5 H 1.0304 0.0462 0.6813 0.058 Uiso 1 1 d R . .
C6 C 1.0927(3) 0.1358(2) 0.6217(6) 0.0554(9) Uani 1 1 d . . .
H6 H 1.1628 0.1186 0.6012 0.066 Uiso 1 1 d R . .
C7 C 1.0653(3) 0.20409(19) 0.6020(6) 0.0578(10) Uani 1 1 d . . .
H7 H 1.1175 0.2368 0.5645 0.069 Uiso 1 1 d R . .
C8 C 0.9619(3) 0.22666(17) 0.6302(5) 0.0504(8) Uani 1 1 d . . .
H8 H 0.9462 0.2768 0.6139 0.061 Uiso 1 1 d R . .
C9 C 0.8885(3) 0.17927(15) 0.6778(4) 0.0362(6) Uani 1 1 d . . .
C10 C 0.7739(3) 0.19608(15) 0.7038(4) 0.0365(6) Uani 1 1 d . . .
C11 C 0.7302(3) 0.26184(17) 0.6955(5) 0.0481(8) Uani 1 1 d . . .
H11 H 0.7776 0.3027 0.6819 0.058 Uiso 1 1 d R . .
C12 C 0.6203(3) 0.27131(18) 0.7149(6) 0.0560(9) Uani 1 1 d . . .
H12 H 0.5876 0.3119 0.7061 0.067 Uiso 1 1 d R . .
C13 C 0.5574(3) 0.21534(19) 0.7423(5) 0.0529(9) Uani 1 1 d . . .
H13 H 0.4806 0.2228 0.7564 0.063 Uiso 1 1 d R . .
C14 C 0.6059(3) 0.15117(17) 0.7526(5) 0.0453(8) Uani 1 1 d . . .
H14 H 0.5574 0.1083 0.7661 0.054 Uiso 1 1 d 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
Cu1 0.0287(2) 0.0244(2) 0.0587(3) 0.00262(15) 0.00997(16) -0.00038(13)
Cl1 0.0352(4) 0.0575(5) 0.0407(4) -0.0012(3) 0.0078(3) -0.0049(3)
O1 0.0475(14) 0.0329(12) 0.109(2) 0.0123(13) 0.0214(14) 0.0125(11)
O2 0.0299(11) 0.0306(11) 0.0863(18) 0.0044(11) 0.0158(11) 0.0005(9)
O3 0.094(2) 0.110(3) 0.0480(17) 0.0133(16) 0.0143(16) 0.018(2)
O13 0.0330(12) 0.0622(16) 0.0586(15) 0.0034(12) 0.0107(10) 0.0016(11)
N1 0.0295(12) 0.0306(12) 0.0411(13) -0.0006(10) 0.0068(10) 0.0014(10)
N2 0.0347(13) 0.0294(12) 0.0483(15) 0.0012(10) 0.0097(11) -0.0015(10)
N3 0.0330(13) 0.0312(13) 0.0463(15) -0.0003(10) 0.0023(11) 0.0011(10)
C1 0.0346(16) 0.0322(15) 0.0509(18) -0.0015(13) 0.0095(13) 0.0019(12)
C2 0.0354(15) 0.0273(14) 0.0428(16) -0.0006(12) 0.0074(12) -0.0023(12)
C3 0.056(2) 0.0403(19) 0.088(3) 0.0197(19) 0.026(2) -0.0042(16)
C4 0.055(2) 0.0375(18) 0.089(3) -0.0146(18) 0.010(2) -0.0119(16)
C5 0.0444(18) 0.0346(16) 0.070(2) 0.0025(15) 0.0214(16) 0.0013(14)
C6 0.047(2) 0.052(2) 0.074(3) 0.0020(18) 0.0269(18) -0.0034(16)
C7 0.056(2) 0.0443(19) 0.079(3) 0.0061(18) 0.0287(19) -0.0126(17)
C8 0.055(2) 0.0331(16) 0.065(2) 0.0038(15) 0.0173(17) -0.0073(15)
C9 0.0385(16) 0.0290(14) 0.0394(16) -0.0004(12) 0.0046(12) -0.0031(12)
C10 0.0409(16) 0.0295(14) 0.0366(15) 0.0017(11) 0.0030(12) 0.0002(12)
C11 0.055(2) 0.0320(16) 0.056(2) 0.0039(14) 0.0100(16) 0.0055(14)
C12 0.061(2) 0.0373(18) 0.068(2) 0.0047(16) 0.0123(18) 0.0197(16)
C13 0.0427(19) 0.053(2) 0.061(2) 0.0009(17) 0.0082(16) 0.0152(16)
C14 0.0329(16) 0.0409(17) 0.060(2) 0.0001(15) 0.0055(14) 0.0033(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
Cu1 O2 1.916(2) . ?
Cu1 N2 1.985(3) . ?
Cu1 N1 2.005(2) . ?
Cu1 N3 2.011(3) . ?
Cu1 O13 2.421(3) . ?
Cl1 O7 1.407(8) . ?
Cl1 O11 1.410(8) . ?
Cl1 O10 1.418(7) . ?
Cl1 O3 1.419(3) . ?
Cl1 O6 1.424(4) . ?
Cl1 O9 1.425(8) . ?
Cl1 O12 1.429(7) . ?
Cl1 O5 1.432(5) . ?
Cl1 O8 1.460(7) . ?
Cl1 O4 1.463(4) . ?
O1 C1 1.220(4) . ?
O2 C1 1.274(4) . ?
O13 H13A 0.8638 . ?
O13 H13B 0.8979 . ?
N1 C2 1.466(4) . ?
N1 H1A 0.9306 . ?
N1 H1B 0.9532 . ?
N2 C5 1.335(4) . ?
N2 C9 1.346(4) . ?
N3 C14 1.336(4) . ?
N3 C10 1.346(4) . ?
C1 C2 1.498(4) . ?
C2 C3 1.498(4) . ?
C2 C4 1.504(4) . ?
C3 C4 1.483(6) . ?
C3 H3A 0.8833 . ?
C3 H3B 1.0529 . ?
C4 H4A 1.0348 . ?
C4 H4B 0.9661 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9011 . ?
C6 C7 1.373(5) . ?
C6 H6 0.9554 . ?
C7 C8 1.386(5) . ?
C7 H7 0.9827 . ?
C8 C9 1.383(4) . ?
C8 H8 0.9981 . ?
C9 C10 1.480(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.381(5) . ?
C11 H11 1.0004 . ?
C12 C13 1.373(5) . ?
C12 H12 0.8816 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9693 . ?
C14 H14 1.0402 . ?

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
O2 Cu1 N2 93.00(10) . . ?
O2 Cu1 N1 84.92(9) . . ?
N2 Cu1 N1 169.11(11) . . ?
O2 Cu1 N3 174.52(10) . . ?
N2 Cu1 N3 81.52(10) . . ?
N1 Cu1 N3 100.51(10) . . ?
O2 Cu1 O13 95.73(10) . . ?
N2 Cu1 O13 88.69(10) . . ?
N1 Cu1 O13 102.15(9) . . ?
N3 Cu1 O13 83.93(9) . . ?
O11 Cl1 O10 112.0(7) . . ?
O7 Cl1 O3 124.5(7) . . ?
O11 Cl1 O3 97.4(9) . . ?
O10 Cl1 O3 115.2(5) . . ?
O7 Cl1 O6 114.2(7) . . ?
O10 Cl1 O6 118.7(5) . . ?
O3 Cl1 O6 117.4(3) . . ?
O7 Cl1 O9 111.6(7) . . ?
O11 Cl1 O9 156.4(11) . . ?
O3 Cl1 O9 103.4(7) . . ?
O11 Cl1 O12 113.8(7) . . ?
O10 Cl1 O12 111.5(5) . . ?
O3 Cl1 O12 106.2(5) . . ?
O3 Cl1 O5 110.1(3) . . ?
O6 Cl1 O5 108.4(3) . . ?
O7 Cl1 O8 109.5(6) . . ?
O10 Cl1 O8 146.7(7) . . ?
O3 Cl1 O8 98.0(6) . . ?
O9 Cl1 O8 108.3(7) . . ?
O3 Cl1 O4 103.7(3) . . ?
O6 Cl1 O4 108.9(3) . . ?
O5 Cl1 O4 107.9(3) . . ?
C1 O2 Cu1 117.05(19) . . ?
Cu1 O13 H13A 109.8 . . ?
Cu1 O13 H13B 105.6 . . ?
H13A O13 H13B 102.8 . . ?
C2 N1 Cu1 108.27(17) . . ?
C2 N1 H1A 110.1 . . ?
Cu1 N1 H1A 107.5 . . ?
C2 N1 H1B 111.5 . . ?
Cu1 N1 H1B 105.2 . . ?
H1A N1 H1B 113.9 . . ?
C5 N2 C9 119.5(3) . . ?
C5 N2 Cu1 125.8(2) . . ?
C9 N2 Cu1 114.7(2) . . ?
C14 N3 C10 119.4(3) . . ?
C14 N3 Cu1 126.7(2) . . ?
C10 N3 Cu1 113.7(2) . . ?
O1 C1 O2 123.5(3) . . ?
O1 C1 C2 120.5(3) . . ?
O2 C1 C2 115.9(3) . . ?
N1 C2 C3 119.3(3) . . ?
N1 C2 C1 113.2(2) . . ?
C3 C2 C1 118.6(3) . . ?
N1 C2 C4 119.6(3) . . ?
C3 C2 C4 59.2(3) . . ?
C1 C2 C4 116.8(3) . . ?
C4 C3 C2 60.6(2) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3B 118.0 . . ?
C2 C3 H3B 117.3 . . ?
H3A C3 H3B 112.2 . . ?
C3 C4 C2 60.2(2) . . ?
C3 C4 H4A 119.6 . . ?
C2 C4 H4A 115.9 . . ?
C3 C4 H4B 117.7 . . ?
C2 C4 H4B 113.9 . . ?
H4A C4 H4B 116.8 . . ?
N2 C5 C6 122.3(3) . . ?
N2 C5 H5 116.4 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C7 118.6(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 121.7 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 118.7(3) . . ?
C9 C8 H8 124.8 . . ?
C7 C8 H8 116.5 . . ?
N2 C9 C8 121.1(3) . . ?
N2 C9 C10 114.8(3) . . ?
C8 C9 C10 124.1(3) . . ?
N3 C10 C11 121.2(3) . . ?
N3 C10 C9 114.8(3) . . ?
C11 C10 C9 124.0(3) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 121.5 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 118.2 . . ?
C11 C12 H12 122.6 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 118.3 . . ?
C14 C13 H13 122.4 . . ?
N3 C14 C13 121.8(3) . . ?
N3 C14 H14 118.4 . . ?
C13 C14 H14 119.7 . . ?