 
# ol0068750.cif

data_global
 
#============================================================================  
# 1. SUBMISSION DETAILS
 
loop_
_publ_contact_author          
_publ_contact_author_address
      'Dr. Jeanette A. Krause Bauer'
;     Department of Chemistry
      University of Cincinnati
      PO Box 210172
      Cincinnati, OHIO 45221-0172
;
_publ_contact_author_phone        '513 556 9226'
_publ_contact_author_fax          '513 556 9239'
_publ_contact_author_email        jeanette.krause@uc.edu
 
_publ_requested_journal           'Organic Letters'
_publ_requested_category          ?
_publ_requested_coeditor_name     ?
 
_publ_contact_letter
;
CIF file for manuscript number o10068750.
;
#============================================================================  
# 2. TITLE AND AUTHOR LIST
 
_publ_section_title
;
Photolysis of α-Azidoacetophenones: Trapping of Triplet Alkyl Nitrenes
in Solution
;
 
# The loop structure below should contain the names and addresses of all 
# authors, in the required order of publication. Repeat as necessary.  

loop_
 _publ_author_name
 _publ_author_address
     'Mandel, Sarah'
;     Department of Chemistry
      University of Cincinnati
      PO Box 210172
      Cincinnati, OHIO 45221-0172
;
     'Krause Bauer, Jeanette A.'
;     Department of Chemistry
      University of Cincinnati
      PO Box 210172
      Cincinnati, OHIO 45221-0172
;
     'Gudmundsdóttir, Anna D.'
;     Department of Chemistry
      University of Cincinnati
      PO Box 210172
      Cincinnati, OHIO 45221-0172
;

#============================================================================
data_3a 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             α-benzamidoacetophenone 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C15 H13 N O2' 
_chemical_formula_weight          239.26 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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' 
 '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                    13.0629(15) 
_cell_length_b                    5.3745(6) 
_cell_length_c                    17.450(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  99.449(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1208.5(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     1707 
_cell_measurement_theta_min       2.37 
_cell_measurement_theta_max       28.30 
 
_exptl_crystal_description        rod 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.34 
_exptl_crystal_size_mid           0.14 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.315 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              504 
_exptl_absorpt_coefficient_mu     0.088 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1996)' 
_exptl_absorpt_correction_T_min   0.9708 
_exptl_absorpt_correction_T_max   0.9930 
 
_exptl_special_details 
; 
The crystal was coated with a light film of epoxy resin and 
mounted on the tip of a glass fiber.
 
The first 50 frames of data were recollected for a decay correction.   
The decay correction was applied simultaneously with the absorption   
correction in SADABS. No formal meaure of the extent of decay is  
printed out by this program.

The final unit cell is obtained from the refinement of the XYZ 
weighted centroids of reflections above 20 σ(I).
; 
 
_diffrn_ambient_temperature       296(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   'SMART 1K CCD' 
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  0.75
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             7654 
_diffrn_reflns_av_R_equivalents   0.0629 
_diffrn_reflns_av_sigmaI/netI     0.0665 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        17 
_diffrn_reflns_limit_k_min        -5 
_diffrn_reflns_limit_k_max        7 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        23 
_diffrn_reflns_theta_min          2.37 
_diffrn_reflns_theta_max          28.30 
_reflns_number_total              2984 
_reflns_number_gt                 1551 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'SMART v5.054' 
_computing_cell_refinement        'SMART v5.054' 
_computing_data_reduction         'SAINT v5.A06' 
_computing_structure_solution     'SHELXTL v5.03' 
_computing_structure_refinement   'SHELXTL v5.03' 
_computing_molecular_graphics     'SHELXTL v5.03' 
_computing_publication_material   'SHELXTL v5.03' 

_refine_special_details 
; 
Refinement on F² for ALL reflections except for 0 with very negative F² 
or flagged by the user for potential systematic errors.  Weighted R-factors 
wR and all goodnesses of fit S are based on F², conventional R-factors R 
are based on F, with F set to zero for negative F². The threshold 
expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 
etc and is not relevant to the choice of reflections for refinement.  
R-factors based on F² are statistically about twice as large as those 
based on F, and R-factors based on ALL data will be even larger. 
 
The hydrogen atom on the nitrogen was found directly and held fixed
in subsequent refinements. The remaining hydrogen atom positions
were calculated based on geomtrical criteria and treated with a
riding model. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0635P)²+0.0087P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0024(16) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2984 
_refine_ls_number_parameters      164 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1252 
_refine_ls_R_factor_gt            0.0582 
_refine_ls_wR_factor_ref          0.1489 
_refine_ls_wR_factor_gt           0.1213 
_refine_ls_goodness_of_fit_ref    1.155 
_refine_ls_restrained_S_all       1.000 
_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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
O1 O -0.04196(13) 0.1725(3) 0.38643(9) 0.0693(5) Uani 1 d . . 
O2 O -0.17853(11) 0.8715(3) 0.24072(8) 0.0595(5) Uani 1 d . . 
N1 N -0.13517(11) 0.4783(3) 0.27695(9) 0.0465(5) Uani 1 d . . 
H1 H -0.1589 0.2920 0.2787 0.056 Uiso 1 d . . 
C1 C 0.09881(14) 0.4299(4) 0.43895(10) 0.0397(5) Uani 1 d . . 
C2 C 0.1291(2) 0.2709(4) 0.50123(11) 0.0478(5) Uani 1 d . . 
H2 H 0.0901(2) 0.1292(4) 0.50680(11) 0.057 Uiso 1 calc R . 
C3 C 0.2164(2) 0.3207(4) 0.55482(13) 0.0551(6) Uani 1 d . . 
H3 H 0.2358(2) 0.2135(4) 0.59653(13) 0.066 Uiso 1 calc R . 
C4 C 0.2747(2) 0.5288(5) 0.54664(13) 0.0575(6) Uani 1 d . . 
H4 H 0.3335(2) 0.5624(5) 0.58294(13) 0.069 Uiso 1 calc R . 
C5 C 0.2465(2) 0.6877(4) 0.48510(13) 0.0576(6) Uani 1 d . . 
H5 H 0.2868(2) 0.8270(4) 0.47944(13) 0.069 Uiso 1 calc R . 
C6 C 0.1582(2) 0.6407(4) 0.43155(12) 0.0491(5) Uani 1 d . . 
H6 H 0.1385(2) 0.7502(4) 0.39052(12) 0.059 Uiso 1 calc R . 
C7 C 0.0033(2) 0.3690(4) 0.38292(11) 0.0430(5) Uani 1 d . . 
C8 C -0.03572(14) 0.5551(4) 0.32104(11) 0.0461(5) Uani 1 d . . 
H8A H -0.04338(14) 0.7156(4) 0.34483(11) 0.055 Uiso 1 calc R . 
H8B H 0.01448(14) 0.5727(4) 0.28615(11) 0.055 Uiso 1 calc R . 
C9 C -0.20149(15) 0.6483(4) 0.24124(11) 0.0440(5) Uani 1 d . . 
C10 C -0.30514(14) 0.5614(4) 0.20054(11) 0.0433(5) Uani 1 d . . 
C11 C -0.3542(2) 0.3498(4) 0.22207(14) 0.0572(6) Uani 1 d . . 
H11 H -0.3216(2) 0.2498(4) 0.26232(14) 0.069 Uiso 1 calc R . 
C12 C -0.4521(2) 0.2885(5) 0.1831(2) 0.0731(8) Uani 1 d . . 
H12 H -0.4858(2) 0.1484(5) 0.1979(2) 0.088 Uiso 1 calc R . 
C13 C -0.4998(2) 0.4331(5) 0.1228(2) 0.0748(8) Uani 1 d . . 
H13 H -0.5654(2) 0.3901(5) 0.0969(2) 0.090 Uiso 1 calc R . 
C14 C -0.4511(2) 0.6404(5) 0.10056(14) 0.0682(7) Uani 1 d . . 
H14 H -0.4831(2) 0.7368(5) 0.05919(14) 0.082 Uiso 1 calc R . 
C15 C -0.3549(2) 0.7052(5) 0.13965(12) 0.0554(6) Uani 1 d . . 
H15 H -0.3226(2) 0.8478(5) 0.12507(12) 0.066 Uiso 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 0.0739(11) 0.0453(10) 0.0774(11) 0.0067(8) -0.0211(9) -0.0162(8) 
O2 0.0544(9) 0.0479(10) 0.0691(10) 0.0070(8) -0.0105(7) -0.0064(7) 
N1 0.0389(9) 0.0440(10) 0.0521(9) 0.0004(8) -0.0057(7) 0.0023(8) 
C1 0.0394(11) 0.0357(11) 0.0420(10) -0.0033(9) 0.0014(8) 0.0032(8) 
C2 0.0474(12) 0.0456(13) 0.0484(11) 0.0032(10) 0.0024(9) 0.0037(10) 
C3 0.0511(13) 0.061(2) 0.0504(12) 0.0044(11) -0.0002(10) 0.0111(11) 
C4 0.0439(12) 0.065(2) 0.0588(13) -0.0126(13) -0.0055(10) 0.0046(12) 
C5 0.0494(13) 0.0516(14) 0.0686(14) -0.0047(12) 0.0002(11) -0.0052(11) 
C6 0.0459(12) 0.0435(13) 0.0551(12) 0.0029(10) -0.0002(9) -0.0001(10) 
C7 0.0450(11) 0.0368(12) 0.0456(11) -0.0034(9) 0.0029(9) 0.0029(10) 
C8 0.0382(11) 0.0482(13) 0.0486(11) 0.0032(10) -0.0025(9) 0.0033(9) 
C9 0.0414(11) 0.0467(14) 0.0422(11) 0.0003(10) 0.0018(8) -0.0001(10) 
C10 0.0375(11) 0.0434(13) 0.0478(11) -0.0043(10) 0.0031(9) 0.0023(9) 
C11 0.0494(13) 0.0470(14) 0.0725(14) 0.0026(12) 0.0023(11) 0.0000(11) 
C12 0.0546(15) 0.054(2) 0.107(2) -0.004(2) 0.0037(14) -0.0141(12) 
C13 0.0452(14) 0.075(2) 0.096(2) -0.016(2) -0.0143(13) -0.0038(14) 
C14 0.0520(14) 0.072(2) 0.072(2) 0.0003(14) -0.0160(12) 0.0040(13) 
C15 0.0469(13) 0.057(2) 0.0578(13) 0.0064(11) -0.0036(10) -0.0013(10) 
 
_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 1.217(2) . y 
O2 C9 1.237(2) . y 
N1 C9 1.340(2) . y 
N1 C8 1.457(2) . y 
C1 C2 1.388(3) . y 
C1 C6 1.391(3) . y 
C1 C7 1.489(3) . y 
C2 C3 1.376(3) . y 
C3 C4 1.374(3) . y 
C4 C5 1.374(3) . y 
C5 C6 1.383(3) . y 
C7 C8 1.499(3) . y 
C9 C10 1.497(3) . y 
C10 C15 1.386(3) . y 
C10 C11 1.387(3) . y 
C11 C12 1.387(3) . y 
C12 C13 1.373(4) . y 
C13 C14 1.370(4) . y 
C14 C15 1.372(3) . y 
 
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 
C9 N1 C8 120.3(2) . . y 
C2 C1 C6 118.8(2) . . y 
C2 C1 C7 118.6(2) . . y 
C6 C1 C7 122.5(2) . . y 
C3 C2 C1 120.7(2) . . y 
C4 C3 C2 119.9(2) . . y 
C3 C4 C5 120.3(2) . . y 
C4 C5 C6 120.1(2) . . y 
C5 C6 C1 120.1(2) . . y 
O1 C7 C1 121.3(2) . . y 
O1 C7 C8 120.3(2) . . y 
C1 C7 C8 118.4(2) . . y 
N1 C8 C7 111.1(2) . . y 
O2 C9 N1 121.7(2) . . y 
O2 C9 C10 120.1(2) . . y 
N1 C9 C10 118.2(2) . . y 
C15 C10 C11 119.0(2) . . y 
C15 C10 C9 117.6(2) . . y 
C11 C10 C9 123.3(2) . . y 
C12 C11 C10 119.5(2) . . y 
C13 C12 C11 120.5(2) . . y 
C14 C13 C12 120.3(2) . . y 
C13 C14 C15 119.7(2) . . y 
C14 C15 C10 121.0(2) . . y 
 
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 
 C6 C1 C2 C3 0.1(3) . . . . y 
 C7 C1 C2 C3 -179.5(2) . . . . y 
 C1 C2 C3 C4 -0.4(3) . . . . y 
 C2 C3 C4 C5 -0.1(3) . . . . y 
 C3 C4 C5 C6 0.9(3) . . . . y 
 C4 C5 C6 C1 -1.3(3) . . . . y 
 C2 C1 C6 C5 0.8(3) . . . . y 
 C7 C1 C6 C5 -179.7(2) . . . . y 
 C2 C1 C7 O1 -7.3(3) . . . . y 
 C6 C1 C7 O1 173.2(2) . . . . y 
 C2 C1 C7 C8 173.3(2) . . . . y 
 C6 C1 C7 C8 -6.3(3) . . . . y 
 C9 N1 C8 C7 154.3(2) . . . . y 
 O1 C7 C8 N1 6.8(3) . . . . y 
 C1 C7 C8 N1 -173.8(2) . . . . y 
 C8 N1 C9 O2 4.2(3) . . . . y 
 C8 N1 C9 C10 -176.5(2) . . . . y 
 O2 C9 C10 C15 25.1(3) . . . . y
 N1 C9 C10 C15 -154.2(2) . . . . y 
 O2 C9 C10 C11 -153.2(2) . . . . y 
 N1 C9 C10 C11 27.5(3) . . . . y 
 C15 C10 C11 C12 -0.9(3) . . . . y 
 C9 C10 C11 C12 177.4(2) . . . . y 
 C10 C11 C12 C13 1.1(4) . . . . y 
 C11 C12 C13 C14 -0.2(4) . . . . y 
 C12 C13 C14 C15 -0.9(4) . . . . y 
 C13 C14 C15 C10 1.2(4) . . . . y 
 C11 C10 C15 C14 -0.3(3) . . . . y 
 C9 C10 C15 C14 -178.6(2) . . . . y 
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_D
 _geom_hbond_site_symmetry_H
 _geom_hbond_site_symmetry_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_publ_flag
 N1 H1 O2 . . 1_545 1.05 2.36 3.352(2) 157.7 y
 C8 H8A O1 . . 1_565 0.97 2.56 3.514(3) 168.1 y
 C8 H8B O2 . . 2_545 0.87 2.51 3.310(2) 139.5 y
 


_refine_diff_density_max    0.178 
_refine_diff_density_min   -0.169 
_refine_diff_density_rms    0.037 

#===END

