# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Lin, Qing'
'Lim, Reyna'

_publ_contact_author_name        'Lin, Qing'
_publ_contact_author_email       qinglin@buffalo.edu

_publ_section_title              
;
Azirine Ligation: Fast and Selective Protein Conjugation
via Photoinduced Azirine-Alkene Cycloaddition
;

# Attachment '- ubql01.cif'

_publ_section_references         
;

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C.,

Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999).

SIR97, J. Appl. Cryst. 32, 115-119.

Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA.

Bruker (2009). APEX2 V2009.9-0, Bruker AXS, Inc., Madison, WI, USA.

Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen,
Germany.

Sheldrick, G. M. (2008). Acta. Cryst. A64, 112-122.

;

data_ubql01
_database_code_depnum_ccdc_archive 'CCDC 786850'
#TrackingRef '- ubql01.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ubql01
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N O'
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_weight         209.24
_chemical_absolute_configuration unk

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 1 21 1'

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

_cell_length_a                   5.4973(7)
_cell_length_b                   8.3407(11)
_cell_length_c                   11.8458(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.166(3)
_cell_angle_gamma                90.00
_cell_volume                     543.14(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    2465
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      25.85

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100.0(1)
_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 APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9617
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1325
_reflns_number_gt                1011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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.

Since the major enantiomer could not be determined by anomalous dispersion
effects, it was assigned arbitrarily. All reflections, including Friedel
opposites, were merged.

The structure refined as a pseudo-merohedral twin, with a mass ratio of
53:47. The application of twin law, [ 1 0 0 / 0 -1 0 / 0 0 -1 ], a 180
degree rotation about direct lattice [ 1 0 0 ], reduced the R1 residual
from 24.4 % to 5.9 %.
;

_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^)+(0.1070P)^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     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(10)
_refine_ls_number_reflns         1325
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_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
O1 O -0.2976(11) 0.9318(5) 0.5881(4) 0.0374(13) Uani 1 1 d . . .
H1 H -0.2013 1.0040 0.6094 0.056 Uiso 1 1 calc R . .
N1 N -0.0090(13) 0.1765(6) 0.6627(4) 0.0399(15) Uani 1 1 d . . .
C1 C 0.0591(14) 0.3177(7) 0.6736(4) 0.0328(15) Uani 1 1 d . . .
C2 C 0.2398(14) 0.2098(7) 0.7249(5) 0.0305(13) Uani 1 1 d . . .
H2 H 0.3920 0.1896 0.6811 0.037 Uiso 1 1 calc R . .
C3 C -0.0259(12) 0.4780(8) 0.6510(5) 0.0268(13) Uani 1 1 d . . .
C4 C -0.2471(12) 0.5024(7) 0.5939(5) 0.0297(14) Uani 1 1 d . . .
H4 H -0.3382 0.4120 0.5695 0.036 Uiso 1 1 calc R . .
C5 C -0.3351(13) 0.6532(7) 0.5724(4) 0.0298(14) Uani 1 1 d . . .
H5 H -0.4847 0.6679 0.5334 0.036 Uiso 1 1 calc R . .
C6 C -0.1982(13) 0.7855(7) 0.6097(4) 0.0286(14) Uani 1 1 d . . .
C7 C 0.0219(13) 0.7646(7) 0.6651(5) 0.0297(14) Uani 1 1 d . . .
H7 H 0.1127 0.8554 0.6890 0.036 Uiso 1 1 calc R . .
C8 C 0.1099(13) 0.6116(6) 0.6858(5) 0.0294(14) Uani 1 1 d . . .
H8 H 0.2614 0.5973 0.7232 0.035 Uiso 1 1 calc R . .
C9 C 0.2515(14) 0.1844(6) 0.8476(4) 0.0292(13) Uani 1 1 d . . .
C10 C 0.4472(14) 0.0971(8) 0.8945(6) 0.0399(17) Uani 1 1 d . . .
H10 H 0.5685 0.0541 0.8463 0.048 Uiso 1 1 calc R . .
C11 C 0.4645(18) 0.0734(9) 1.0090(6) 0.048(2) Uani 1 1 d . . .
H11 H 0.5961 0.0137 1.0399 0.058 Uiso 1 1 calc R . .
C12 C 0.2899(13) 0.1368(8) 1.0784(5) 0.0390(16) Uani 1 1 d . . .
H12 H 0.3003 0.1205 1.1577 0.047 Uiso 1 1 calc R . .
C13 C 0.0995(13) 0.2240(9) 1.0340(5) 0.0372(15) Uani 1 1 d . . .
H13 H -0.0189 0.2691 1.0829 0.045 Uiso 1 1 calc R . .
C14 C 0.0797(13) 0.2463(7) 0.9185(5) 0.0338(15) Uani 1 1 d . . .
H14 H -0.0538 0.3048 0.8884 0.041 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
O1 0.058(3) 0.022(2) 0.032(2) 0.0037(16) -0.002(3) 0.001(2)
N1 0.072(5) 0.025(3) 0.023(2) 0.000(2) 0.004(3) 0.002(3)
C1 0.054(4) 0.026(3) 0.019(3) 0.001(2) 0.000(3) 0.005(3)
C2 0.047(4) 0.021(2) 0.024(2) 0.002(2) -0.004(3) 0.005(3)
C3 0.036(4) 0.023(3) 0.022(3) 0.000(2) -0.004(3) 0.002(3)
C4 0.039(4) 0.035(3) 0.016(3) 0.002(2) 0.003(3) -0.007(3)
C5 0.041(4) 0.029(3) 0.019(3) 0.003(2) 0.001(3) 0.001(3)
C6 0.043(4) 0.025(3) 0.018(3) 0.004(2) 0.008(3) 0.003(3)
C7 0.039(4) 0.026(3) 0.024(3) -0.002(2) -0.001(3) -0.006(3)
C8 0.047(4) 0.022(3) 0.019(3) 0.001(2) -0.001(3) -0.001(3)
C9 0.044(4) 0.019(3) 0.024(2) 0.002(2) -0.001(3) 0.002(3)
C10 0.056(5) 0.033(3) 0.031(3) 0.003(3) 0.003(3) 0.008(3)
C11 0.071(6) 0.036(4) 0.037(3) 0.011(3) -0.003(4) 0.004(4)
C12 0.049(4) 0.037(4) 0.031(3) 0.008(3) 0.001(3) 0.000(3)
C13 0.043(4) 0.038(3) 0.031(3) 0.003(3) 0.006(3) 0.002(3)
C14 0.044(4) 0.029(3) 0.028(3) 0.001(3) 0.003(3) 0.001(3)

_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 C6 1.361(7) . ?
O1 H1 0.8400 . ?
N1 C1 1.242(8) . ?
N1 C2 1.576(10) . ?
C1 C3 1.442(9) . ?
C1 C2 1.470(9) . ?
C2 C9 1.470(7) . ?
C2 H2 1.0000 . ?
C3 C8 1.402(9) . ?
C3 C4 1.405(9) . ?
C4 C5 1.370(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(9) . ?
C7 C8 1.387(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.367(8) . ?
C9 C10 1.412(10) . ?
C10 C11 1.374(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C6 O1 H1 109.5 . . ?
C1 N1 C2 61.5(5) . . ?
N1 C1 C3 139.7(7) . . ?
N1 C1 C2 70.5(5) . . ?
C3 C1 C2 149.6(6) . . ?
C1 C2 C9 121.6(6) . . ?
C1 C2 N1 48.0(4) . . ?
C9 C2 N1 118.2(6) . . ?
C1 C2 H2 117.0 . . ?
C9 C2 H2 117.0 . . ?
N1 C2 H2 117.0 . . ?
C8 C3 C4 119.1(6) . . ?
C8 C3 C1 120.7(6) . . ?
C4 C3 C1 120.3(6) . . ?
C5 C4 C3 121.8(6) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
O1 C6 C7 123.5(6) . . ?
O1 C6 C5 115.5(6) . . ?
C7 C6 C5 121.0(6) . . ?
C6 C7 C8 120.2(6) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 119.6(6) . . ?
C7 C8 H8 120.2 . . ?
C3 C8 H8 120.2 . . ?
C14 C9 C10 118.7(5) . . ?
C14 C9 C2 121.7(6) . . ?
C10 C9 C2 119.7(6) . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.3(7) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 120.4(7) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.3(6) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C3 -175.8(10) . . . . ?
N1 C1 C2 C9 -101.0(7) . . . . ?
C3 C1 C2 C9 73.6(13) . . . . ?
C3 C1 C2 N1 174.7(13) . . . . ?
C1 N1 C2 C9 108.5(6) . . . . ?
N1 C1 C3 C8 175.4(8) . . . . ?
C2 C1 C3 C8 3.2(14) . . . . ?
N1 C1 C3 C4 -4.4(12) . . . . ?
C2 C1 C3 C4 -176.7(9) . . . . ?
C8 C3 C4 C5 -0.8(9) . . . . ?
C1 C3 C4 C5 179.0(6) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C4 C5 C6 O1 -178.6(5) . . . . ?
C4 C5 C6 C7 1.0(8) . . . . ?
O1 C6 C7 C8 178.9(6) . . . . ?
C5 C6 C7 C8 -0.7(8) . . . . ?
C6 C7 C8 C3 -0.5(8) . . . . ?
C4 C3 C8 C7 1.2(8) . . . . ?
C1 C3 C8 C7 -178.7(6) . . . . ?
C1 C2 C9 C14 7.0(9) . . . . ?
N1 C2 C9 C14 -48.8(7) . . . . ?
C1 C2 C9 C10 -171.6(6) . . . . ?
N1 C2 C9 C10 132.6(6) . . . . ?
C14 C9 C10 C11 0.5(10) . . . . ?
C2 C9 C10 C11 179.1(7) . . . . ?
C9 C10 C11 C12 -0.5(12) . . . . ?
C10 C11 C12 C13 -0.3(12) . . . . ?
C11 C12 C13 C14 1.2(11) . . . . ?
C10 C9 C14 C13 0.4(9) . . . . ?
C2 C9 C14 C13 -178.2(7) . . . . ?
C12 C13 C14 C9 -1.2(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.89 2.731(7) 174.8 1_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.075