# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
#===========================================================================

# SUBMISSION DETAILS

_publ_contact_author_name        'Paul B. Jones '
_publ_contact_author_address     
;
Department of Chemistry
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
_publ_contact_author_email       jonespb@wfu.edu
_publ_contact_author_fax         '336 758 4656'
_publ_contact_author_phone       '336 758 3708'

_publ_contact_letter             
;
June 14, 2007

This is a CIF submission for a manuscript being submitted
for publication in Journal of Photochemistry and Photobiology
A: Chemistry.

The CIF has passed the IUCR CHECKCIF routines.

Cynthia S. Day
;
_publ_requested_category         ?

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

# TITLE AND AUTHOR LIST
_publ_section_title              
;
Heavy-Atom Effects in the Photochemistry of 1-Alkoxy-9,10-Anthraquinones
;
_publ_section_title_footnote     
;
;
loop_
_publ_author_name
_publ_author_address
R.G.Brinson
;
Department of Chemistry
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
S.J.Sarma
;
Department of Chemistry
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
S.Elkazaz
;
Department of Chemistry
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
P.B.Jones
;
Department of Chemistry
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
#==============================================================================

_publ_section_references         
;
Allen, F. H. (2002). Acta Cryst. B58, 380-388.

Bruker (2001). SHELXTL-NT (Version 6.12). Bruker AXS Inc., Madison,
Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876-881.

North, A.C.T., Phillips, D.C. & Mathews, F.S.(1968) Acta Cryst. A24, 351
- 359.

Bruker (2002). SMART version 5.628 and SAINT version 6.36a.
Bruker AXS Inc., Madison, Wisconsin, USA.

;

#==========================================================
data_a01i2f
_database_code_depnum_ccdc_archive 'CCDC 650843'

_audit_creation_method           SHELXTL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H6 Br N O3'
_chemical_formula_weight         328.12

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.835(3)
_cell_length_b                   8.910(4)
_cell_length_c                   12.876(5)
_cell_angle_alpha                69.902(6)
_cell_angle_beta                 78.323(7)
_cell_angle_gamma                80.933(7)
_cell_volume                     612.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    1373
_cell_measurement_theta_min      3.925
_cell_measurement_theta_max      25.306

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    3.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4994
_exptl_absorpt_correction_T_max  0.9059
_exptl_absorpt_process_details   
;
Data were corrected for absorption effects using the
multi-scan technique (SADABS). The ratio of minimum
to maximum apparent transmission: 0.782445
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(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  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5743
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2979
_reflns_number_gt                2314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0501P)^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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2979
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_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
Br Br 0.34439(6) 0.19863(4) 0.55894(2) 0.04218(14) Uani 1 1 d . . .
O1 O 0.1725(4) 0.1033(3) 0.80444(18) 0.0302(5) Uani 1 1 d . . .
H1 H 0.133(8) 0.077(6) 0.880(4) 0.088(16) Uiso 1 1 d . . .
O2 O 0.1721(4) 0.0792(3) 1.00854(16) 0.0332(5) Uani 1 1 d . . .
O3 O 0.9079(4) 0.4272(3) 0.89229(18) 0.0383(5) Uani 1 1 d . . .
N N 1.0698(5) 0.5646(4) 0.6343(2) 0.0392(6) Uani 1 1 d . . .
C1 C 0.4615(5) 0.2481(4) 0.6683(2) 0.0272(6) Uani 1 1 d . . .
C2 C 0.3548(5) 0.1910(3) 0.7805(2) 0.0251(6) Uani 1 1 d . . .
C3 C 0.4417(5) 0.2287(3) 0.8625(2) 0.0224(6) Uani 1 1 d . . .
C4 C 0.3321(5) 0.1676(3) 0.9806(2) 0.0229(6) Uani 1 1 d . . .
C5 C 0.4195(5) 0.2095(3) 1.0662(2) 0.0244(6) Uani 1 1 d . . .
C6 C 0.3087(5) 0.1583(4) 1.1772(2) 0.0280(6) Uani 1 1 d . . .
H6 H 0.1744 0.1003 1.1971 0.034 Uiso 1 1 calc R . .
C7 C 0.3950(6) 0.1923(4) 1.2585(2) 0.0332(7) Uani 1 1 d . . .
H7 H 0.3199 0.1570 1.3343 0.040 Uiso 1 1 calc R . .
C8 C 0.5916(6) 0.2781(4) 1.2296(3) 0.0343(7) Uani 1 1 d . . .
H8 H 0.6505 0.3002 1.2859 0.041 Uiso 1 1 calc R . .
C9 C 0.7011(5) 0.3309(4) 1.1195(2) 0.0292(6) Uani 1 1 d . . .
H9 H 0.8349 0.3892 1.1004 0.035 Uiso 1 1 calc R . .
C10 C 0.6152(5) 0.2986(3) 1.0362(2) 0.0242(6) Uani 1 1 d . . .
C11 C 0.7330(5) 0.3558(3) 0.9183(2) 0.0254(6) Uani 1 1 d . . .
C12 C 0.6336(5) 0.3222(3) 0.8307(2) 0.0225(6) Uani 1 1 d . . .
C13 C 0.7336(5) 0.3793(3) 0.7182(2) 0.0268(6) Uani 1 1 d . . .
C14 C 0.6453(5) 0.3415(4) 0.6368(2) 0.0293(6) Uani 1 1 d . . .
H14 H 0.7133 0.3808 0.5601 0.035 Uiso 1 1 calc R . .
C15 C 0.9241(5) 0.4824(4) 0.6769(2) 0.0306(7) Uani 1 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
Br 0.0578(2) 0.0535(2) 0.02424(17) -0.01613(15) -0.01117(14) -0.01707(17)
O1 0.0335(11) 0.0362(12) 0.0264(11) -0.0117(10) -0.0065(9) -0.0133(9)
O2 0.0372(11) 0.0420(13) 0.0245(10) -0.0099(9) -0.0018(9) -0.0215(10)
O3 0.0371(12) 0.0506(14) 0.0319(11) -0.0107(11) -0.0035(9) -0.0261(10)
N 0.0388(15) 0.0527(18) 0.0268(13) -0.0113(13) 0.0022(11) -0.0203(14)
C1 0.0332(15) 0.0328(16) 0.0202(13) -0.0123(12) -0.0098(11) -0.0009(13)
C2 0.0269(14) 0.0262(15) 0.0246(13) -0.0085(12) -0.0064(11) -0.0057(12)
C3 0.0223(13) 0.0244(14) 0.0206(13) -0.0061(11) -0.0047(10) -0.0037(11)
C4 0.0259(13) 0.0234(14) 0.0215(13) -0.0080(11) -0.0042(10) -0.0056(11)
C5 0.0265(14) 0.0260(15) 0.0229(13) -0.0090(12) -0.0046(11) -0.0051(12)
C6 0.0300(15) 0.0320(16) 0.0235(14) -0.0110(12) -0.0019(11) -0.0056(13)
C7 0.0440(18) 0.0370(18) 0.0215(14) -0.0123(13) -0.0053(13) -0.0060(14)
C8 0.0472(18) 0.0382(18) 0.0264(15) -0.0167(14) -0.0138(13) -0.0048(15)
C9 0.0312(15) 0.0299(16) 0.0306(15) -0.0120(13) -0.0070(12) -0.0074(13)
C10 0.0270(14) 0.0240(14) 0.0238(13) -0.0091(12) -0.0065(11) -0.0024(11)
C11 0.0283(14) 0.0253(15) 0.0250(14) -0.0080(12) -0.0055(11) -0.0083(12)
C12 0.0240(13) 0.0222(14) 0.0228(13) -0.0083(11) -0.0051(10) -0.0023(11)
C13 0.0261(14) 0.0274(15) 0.0253(14) -0.0063(12) -0.0021(11) -0.0061(12)
C14 0.0345(16) 0.0328(16) 0.0185(13) -0.0056(12) -0.0014(11) -0.0070(13)
C15 0.0314(15) 0.0372(17) 0.0219(14) -0.0087(13) -0.0008(12) -0.0055(14)

_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
Br C1 1.886(3) . ?
O1 C2 1.342(3) . ?
O1 H1 0.91(5) . ?
O2 C4 1.234(3) . ?
O3 C11 1.216(3) . ?
N C15 1.137(4) . ?
C1 C14 1.371(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.414(4) . ?
C3 C12 1.411(4) . ?
C3 C4 1.472(4) . ?
C4 C5 1.477(4) . ?
C5 C6 1.392(4) . ?
C5 C10 1.407(4) . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.481(4) . ?
C11 C12 1.499(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.411(4) . ?
C13 C15 1.452(4) . ?
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
C2 O1 H1 103(3) . . ?
C14 C1 C2 121.2(2) . . ?
C14 C1 Br 119.8(2) . . ?
C2 C1 Br 119.0(2) . . ?
O1 C2 C1 117.7(2) . . ?
O1 C2 C3 123.2(2) . . ?
C1 C2 C3 119.0(2) . . ?
C12 C3 C2 119.9(2) . . ?
C12 C3 C4 120.7(2) . . ?
C2 C3 C4 119.3(2) . . ?
O2 C4 C3 120.4(2) . . ?
O2 C4 C5 120.2(2) . . ?
C3 C4 C5 119.5(2) . . ?
C6 C5 C10 120.2(3) . . ?
C6 C5 C4 119.5(3) . . ?
C10 C5 C4 120.3(2) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 119.3(3) . . ?
C9 C10 C11 119.9(2) . . ?
C5 C10 C11 120.8(2) . . ?
O3 C11 C10 121.2(3) . . ?
O3 C11 C12 120.2(3) . . ?
C10 C11 C12 118.6(2) . . ?
C13 C12 C3 119.6(2) . . ?
C13 C12 C11 120.4(2) . . ?
C3 C12 C11 119.9(2) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 C15 123.6(3) . . ?
C14 C13 C15 116.3(3) . . ?
C1 C14 C13 120.1(3) . . ?
C1 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N C15 C13 173.2(3) . . ?

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
C14 C1 C2 O1 178.6(3) . . . . ?
Br C1 C2 O1 -0.1(4) . . . . ?
C14 C1 C2 C3 -1.0(4) . . . . ?
Br C1 C2 C3 -179.7(2) . . . . ?
O1 C2 C3 C12 -179.7(3) . . . . ?
C1 C2 C3 C12 -0.2(4) . . . . ?
O1 C2 C3 C4 1.1(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C12 C3 C4 O2 -176.3(3) . . . . ?
C2 C3 C4 O2 2.8(4) . . . . ?
C12 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
O2 C4 C5 C6 -4.8(4) . . . . ?
C3 C4 C5 C6 176.9(3) . . . . ?
O2 C4 C5 C10 174.4(3) . . . . ?
C3 C4 C5 C10 -3.9(4) . . . . ?
C10 C5 C6 C7 -1.5(4) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C5 -1.2(4) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C6 C5 C10 C9 1.9(4) . . . . ?
C4 C5 C10 C9 -177.3(3) . . . . ?
C6 C5 C10 C11 -179.2(3) . . . . ?
C4 C5 C10 C11 1.7(4) . . . . ?
C9 C10 C11 O3 2.0(4) . . . . ?
C5 C10 C11 O3 -177.0(3) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C5 C10 C11 C12 2.3(4) . . . . ?
C2 C3 C12 C13 1.2(4) . . . . ?
C4 C3 C12 C13 -179.7(2) . . . . ?
C2 C3 C12 C11 -177.2(2) . . . . ?
C4 C3 C12 C11 2.0(4) . . . . ?
O3 C11 C12 C13 -3.2(4) . . . . ?
C10 C11 C12 C13 177.5(3) . . . . ?
O3 C11 C12 C3 175.1(3) . . . . ?
C10 C11 C12 C3 -4.2(4) . . . . ?
C3 C12 C13 C14 -1.0(4) . . . . ?
C11 C12 C13 C14 177.3(3) . . . . ?
C3 C12 C13 C15 177.1(3) . . . . ?
C11 C12 C13 C15 -4.6(4) . . . . ?
C2 C1 C14 C13 1.2(4) . . . . ?
Br C1 C14 C13 179.9(2) . . . . ?
C12 C13 C14 C1 -0.2(4) . . . . ?
C15 C13 C14 C1 -178.4(3) . . . . ?
C12 C13 C15 N -172(3) . . . . ?
C14 C13 C15 N 6(3) . . . . ?

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 O2 0.91(5) 1.72(5) 2.562(3) 152(5) .
O1 H1 O2 0.91(5) 2.35(5) 2.977(3) 126(4) 2_557

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.090