# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2011

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Okuma, Kentaro'

_publ_contact_author_name        'Okuma, Kentaro'
_publ_contact_author_email       kokuma@fukuoka-u.ac.jp

_publ_section_title              
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Reaction of Arynes with Amino Acid Esters
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_publ_contact_author_address     
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Department of Chemistry, Fukuoka University
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_publ_contact_author_fax         ' '
_publ_contact_author_phone       ' '

# Submission details
_publ_requested_journal          'Acta Crystallographica Section C '

# Attachment '- full.cif'

# CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98)
data_full
_database_code_depnum_ccdc_archive 'CCDC 815166'
#TrackingRef '- full.cif'

_audit_creation_method           maXus
_publ_section_abstract           
;
We present the crystal and molecular structure of
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_publ_section_comment            
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The study of the titled structure was undertaken to establish its three
dimensional structure. Geometries are tabulated below. All diagrams and
calculations were performed using maXus (Bruker Nonius, Delft & MacScience,
Japan).
;
_publ_section_synopsis           
;

;
_publ_section_exptl_prep         
;

;
_publ_section_exptl_refinement   
;

;
_publ_section_figure_captions    
;

;
_publ_section_acknowledgements   
;

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_chemical_compound_source        'Okuma laboratory'
_exptl_crystal_description       Cube
_exptl_crystal_colour            Colourless
_cell_measurement_temperature    298
_refine_ls_hydrogen_treatment    constr
_diffrn_measurement_device       'DIP Image plate'
_computing_data_collection       'DIP Image plate'
_computing_data_reduction        'maXus (Mackay et al., 1999)'
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18

loop_
_diffrn_radiation_wavelength
1.54184
_diffrn_radiation_wavelength_id  all

_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.07198
_diffrn_orient_matrix_UB_12      -0.02095
_diffrn_orient_matrix_UB_13      0.01918
_diffrn_orient_matrix_UB_21      0.04422
_diffrn_orient_matrix_UB_22      -0.18049
_diffrn_orient_matrix_UB_23      -0.03119
_diffrn_orient_matrix_UB_31      0.00760
_diffrn_orient_matrix_UB_32      -0.01057
_diffrn_orient_matrix_UB_33      0.07192

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_special_details           
;
?
;
_chemical_formula_weight         203.197
_diffrn_radiation_type           ' CuK\a'

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

_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_cell_setting           Monoclinic
_chemical_formula_moiety         'C11 H9 N O3 '
_chemical_formula_sum            'C11 H9 N O3 '
_chemical_name_systematic        
;
?
;
_cell_length_a                   13.1450(11)
_cell_length_b                   5.3200(4)
_cell_length_c                   17.294(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.636(4)
_cell_angle_gamma                90.00
_cell_volume                     957.73(14)
_diffrn_reflns_number            1507
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_full        68.29
_diffrn_measurement_method       IP
_computing_cell_refinement       Scalepack(HKL)
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_exptl_absorpt_coefficient_mu    0.869
_reflns_number_total             1046
_reflns_number_gt                675
_reflns_threshold_expression     >2sigma(I)

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1046
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2169
_refine_ls_wR_factor_gt          0.1934
_refine_ls_goodness_of_fit_ref   1.478
_refine_ls_restrained_S_all      1.478
_refine_ls_shift/su_max          0.224
_refine_ls_shift/su_mean         0.033

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2826(4) 0.0695(9) 0.6588(3) 0.0745(15) Uani 1 d . . .
O2 O -0.0340(4) -0.1907(8) 0.2945(3) 0.0610(13) Uani 1 d . . .
O3 O -0.0775(4) -0.4546(8) 0.3722(3) 0.0632(14) Uani 1 d . . .
N1 N 0.1628(5) 0.1677(10) 0.4179(4) 0.0552(16) Uani 1 d . . .
C1 C 0.2565(6) 0.3521(12) 0.4647(4) 0.0518(17) Uani 1 d . . .
C2 C 0.3201(6) 0.3465(11) 0.5654(4) 0.0530(17) Uani 1 d . . .
C3 C 0.4177(7) 0.5140(14) 0.6287(6) 0.068(2) Uani 1 d . . .
C4 C 0.4501(8) 0.6857(16) 0.5891(6) 0.075(2) Uani 1 d . . .
C5 C 0.3898(8) 0.6880(15) 0.4902(6) 0.073(2) Uani 1 d . . .
C6 C 0.2915(7) 0.5221(12) 0.4251(5) 0.0597(19) Uani 1 d . . .
C7 C 0.2596(6) 0.1440(12) 0.5823(4) 0.0588(18) Uani 1 d . . .
C8 C 0.1582(6) 0.0355(11) 0.4825(4) 0.0480(16) Uani 1 d . . .
C9 C 0.0818(7) -0.1596(13) 0.4655(5) 0.0572(19) Uani 1 d . . .
C10 C -0.0141(6) -0.2620(12) 0.3684(4) 0.0545(17) Uani 1 d . . .
C11 C -0.1773(9) -0.569(2) 0.2790(6) 0.077(2) Uani 1 d . . .
H3 H 0.472(6) 0.486(12) 0.701(5) 0.08(2) Uiso 1 d . . .
H4 H 0.524(7) 0.797(14) 0.634(5) 0.09(2) Uiso 1 d . . .
H5 H 0.405(5) 0.806(10) 0.460(4) 0.042(17) Uiso 1 d . . .
H6 H 0.250(6) 0.526(11) 0.354(5) 0.070(19) Uiso 1 d . . .
H1 H 0.119(5) 0.129(9) 0.360(4) 0.038(16) Uiso 1 d . . .
H9 H 0.095(5) -0.214(10) 0.519(4) 0.046(16) Uiso 1 d . . .
H11A H -0.232(5) -0.674(11) 0.287(4) 0.048(17) Uiso 1 d . . .
H11B H -0.131(7) -0.627(13) 0.256(5) 0.10(3) Uiso 1 d . . .
H11C H -0.257(7) -0.447(13) 0.238(5) 0.08(2) Uiso 1 d . . .

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 0.079(3) 0.087(4) 0.044(3) 0.002(2) 0.031(3) -0.004(3)
O2 0.068(3) 0.065(3) 0.044(3) -0.001(2) 0.031(2) -0.008(2)
O3 0.073(3) 0.058(3) 0.052(3) -0.003(2) 0.035(2) -0.013(2)
N1 0.058(4) 0.064(4) 0.033(3) -0.005(3) 0.023(3) -0.010(3)
C1 0.051(4) 0.059(4) 0.048(4) 0.004(3) 0.032(3) 0.010(4)
C2 0.055(4) 0.046(4) 0.058(4) -0.005(3) 0.035(3) 0.000(3)
C3 0.054(4) 0.068(5) 0.063(5) -0.010(4) 0.026(4) -0.003(4)
C4 0.064(5) 0.072(5) 0.080(6) -0.007(5) 0.040(5) -0.010(4)
C5 0.081(6) 0.065(5) 0.077(5) 0.002(5) 0.050(5) -0.009(4)
C6 0.065(5) 0.056(4) 0.056(4) -0.003(4) 0.036(4) -0.001(4)
C7 0.056(4) 0.061(4) 0.036(3) -0.003(3) 0.016(3) 0.012(4)
C8 0.057(4) 0.046(4) 0.049(4) 0.001(3) 0.036(3) 0.006(4)
C9 0.065(5) 0.063(5) 0.043(4) 0.011(4) 0.032(4) 0.013(4)
C10 0.068(4) 0.044(4) 0.051(4) 0.002(3) 0.036(4) 0.011(4)
C11 0.068(6) 0.092(6) 0.064(5) -0.015(5) 0.037(5) -0.029(6)

_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
O1 C7 1.228(7) . ?
O2 C10 1.200(6) . ?
O3 C10 1.348(7) . ?
O3 C11 1.452(8) . ?
N1 C8 1.352(7) . ?
N1 C1 1.385(8) . ?
C1 C6 1.373(9) . ?
C1 C2 1.397(8) . ?
C2 C3 1.387(9) . ?
C2 C7 1.471(9) . ?
C3 C4 1.357(10) . ?
C4 C5 1.377(10) . ?
C5 C6 1.393(9) . ?
C7 C8 1.510(8) . ?
C8 C9 1.346(9) . ?
C9 C10 1.455(9) . ?
N1 H1 0.82(5) . ?
C3 H3 1.00(6) . ?
C4 H4 0.99(8) . ?
C5 H5 0.91(5) . ?
C6 H6 1.00(6) . ?
C9 H9 0.88(5) . ?
C11 H11A 0.98(5) . ?
C11 H11B 0.95(7) . ?
C11 H11C 1.06(8) . ?

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
C10 O3 C11 115.6(5) . . ?
C8 N1 C1 111.0(5) . . ?
C6 C1 N1 128.6(6) . . ?
C6 C1 C2 120.6(6) . . ?
N1 C1 C2 110.8(6) . . ?
C3 C2 C1 122.0(7) . . ?
C3 C2 C7 131.7(6) . . ?
C1 C2 C7 106.2(6) . . ?
C2 C3 C4 117.3(8) . . ?
C3 C4 C5 120.8(8) . . ?
C4 C5 C6 123.0(8) . . ?
C1 C6 C5 116.2(7) . . ?
O1 C7 C2 130.0(6) . . ?
O1 C7 C8 124.9(6) . . ?
C2 C7 C8 105.0(5) . . ?
C9 C8 N1 128.6(6) . . ?
C9 C8 C7 124.4(6) . . ?
N1 C8 C7 107.0(6) . . ?
C8 C9 C10 123.1(6) . . ?
O2 C10 O3 123.6(6) . . ?
O2 C10 C9 125.6(7) . . ?
O3 C10 C9 110.8(6) . . ?
C8 N1 H1 122(4) . . ?
C1 N1 H1 127(4) . . ?
C2 C3 H3 120(4) . . ?
C4 C3 H3 122(4) . . ?
C3 C4 H4 118(4) . . ?
C5 C4 H4 121(4) . . ?
C4 C5 H5 124(3) . . ?
C6 C5 H5 113(3) . . ?
C1 C6 H6 123(3) . . ?
C5 C6 H6 121(4) . . ?
C8 C9 H9 113(4) . . ?
C10 C9 H9 124(4) . . ?
O3 C11 H11A 109(3) . . ?
O3 C11 H11B 103(4) . . ?
H11A C11 H11B 125(6) . . ?
O3 C11 H11C 110(4) . . ?
H11A C11 H11C 86(5) . . ?
H11B C11 H11C 123(6) . . ?

_diffrn_measured_fraction_theta_max 0.534
_diffrn_measured_fraction_theta_full 0.534
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.070

_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.

Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot
Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge,
Tennessee, USA.

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal
Structures. University of G\"ottingen, Germany.

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