# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_cd214140

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   7.4062(14)
_cell_length_b                   7.4146(14)
_cell_length_c                   16.172(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.997(4)
_cell_angle_gamma                90
_cell_volume                     887.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1761
_cell_measurement_theta_min      5.955
_cell_measurement_theta_max      56.709

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5278
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.520
_diffrn_reflns_theta_max         25.986
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3329
_reflns_number_gt                2453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.931

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   2.4(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1800(4) 0.8878(4) 0.1730(2) 0.0535(8) Uani 1 1 d . . . . .
O1 O 0.9617(3) 1.0772(3) 0.20600(14) 0.0456(6) Uani 1 1 d . . . . .
O2 O 0.5689(3) 0.9337(3) 0.21523(15) 0.0421(6) Uani 1 1 d . . . . .
H2 H 0.4646 0.9051 0.2026 0.063 Uiso 1 1 calc R U . . .
O3 O 0.7721(4) 0.5536(4) 0.3059(2) 0.0733(9) Uani 1 1 d . . . . .
O4 O 0.5437(3) 0.5789(3) 0.21361(17) 0.0545(7) Uani 1 1 d . . . . .
O5 O 0.1438(4) 1.1916(5) 0.4223(2) 0.0838(10) Uani 1 1 d . . . . .
C1 C 1.1057(4) 1.0427(5) 0.1585(2) 0.0434(9) Uani 1 1 d . . . . .
C2 C 1.0769(5) 0.8142(5) 0.2347(2) 0.0540(10) Uani 1 1 d . . . . .
H2A H 1.0967 0.7012 0.2583 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9465(5) 0.9260(5) 0.2554(2) 0.0445(9) Uani 1 1 d . . . . .
C4 C 0.8039(5) 0.9301(5) 0.3183(2) 0.0481(9) Uani 1 1 d . . . . .
H4A H 0.7815 1.0545 0.3335 0.058 Uiso 1 1 calc R U . . .
H4B H 0.8484 0.8676 0.3676 0.058 Uiso 1 1 calc R U . . .
C5 C 0.6248(4) 0.8436(5) 0.2886(2) 0.0377(8) Uani 1 1 d . . . . .
C6 C 0.4846(5) 0.8626(5) 0.3565(2) 0.0431(9) Uani 1 1 d . . . . .
C7 C 0.4624(6) 0.7341(6) 0.4167(2) 0.0624(11) Uani 1 1 d . . . . .
H7 H 0.5338 0.6309 0.4182 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3321(7) 0.7602(8) 0.4753(3) 0.0784(14) Uani 1 1 d . . . . .
H8 H 0.3156 0.6723 0.5154 0.094 Uiso 1 1 calc R U . . .
C9 C 0.2282(6) 0.9115(8) 0.4755(3) 0.0712(13) Uani 1 1 d . . . . .
H9 H 0.1405 0.9255 0.5148 0.085 Uiso 1 1 calc R U . . .
C10 C 0.2531(5) 1.0426(7) 0.4178(2) 0.0580(11) Uani 1 1 d . . . . .
C11 C 0.3819(5) 1.0186(5) 0.3572(2) 0.0496(10) Uani 1 1 d . . . . .
H11 H 0.3983 1.1074 0.3176 0.059 Uiso 1 1 calc R U . . .
C12 C 0.1746(7) 1.3354(7) 0.3678(4) 0.0909(17) Uani 1 1 d . . . . .
H12A H 0.2946 1.3813 0.3777 0.136 Uiso 1 1 calc R U . . .
H12B H 0.0884 1.4295 0.3767 0.136 Uiso 1 1 calc R U . . .
H12C H 0.1617 1.2933 0.3117 0.136 Uiso 1 1 calc R U . . .
C13 C 0.6584(5) 0.6429(5) 0.2714(2) 0.0447(9) Uani 1 1 d . . . . .
C14 C 0.5671(6) 0.3915(5) 0.1899(3) 0.0732(14) Uani 1 1 d . . . . .
H14A H 0.6768 0.3790 0.1605 0.110 Uiso 1 1 calc R U . . .
H14B H 0.4665 0.3543 0.1549 0.110 Uiso 1 1 calc R U . . .
H14C H 0.5734 0.3175 0.2386 0.110 Uiso 1 1 calc R U . . .
C15 C 1.1575(5) 1.1794(5) 0.0985(2) 0.0446(9) Uani 1 1 d . . . . .
C16 C 1.0950(5) 1.3552(5) 0.1026(2) 0.0534(10) Uani 1 1 d . . . . .
H16 H 1.0165 1.3880 0.1437 0.064 Uiso 1 1 calc R U . . .
C17 C 1.1489(6) 1.4819(6) 0.0459(3) 0.0641(12) Uani 1 1 d . . . . .
H17 H 1.1091 1.6005 0.0497 0.077 Uiso 1 1 calc R U . . .
C18 C 1.2615(6) 1.4329(7) -0.0163(3) 0.0679(13) Uani 1 1 d . . . . .
H18 H 1.2945 1.5174 -0.0555 0.082 Uiso 1 1 calc R U . . .
C19 C 1.3249(6) 1.2596(7) -0.0205(2) 0.0642(11) Uani 1 1 d . . . . .
H19 H 1.4026 1.2275 -0.0620 0.077 Uiso 1 1 calc R U . . .
C20 C 1.2743(5) 1.1327(6) 0.0366(2) 0.0557(11) Uani 1 1 d . . . . .
H20 H 1.3184 1.0155 0.0336 0.067 Uiso 1 1 calc R U . . .


_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
N1 C1 1.291(5) . ?
N1 C2 1.389(5) . ?
O1 C1 1.360(4) . ?
O1 C3 1.384(4) . ?
O2 C5 1.411(4) . ?
O2 H2 0.8200 . ?
O3 C13 1.194(4) . ?
O4 C13 1.329(4) . ?
O4 C14 1.453(5) . ?
O5 C10 1.373(5) . ?
O5 C12 1.407(6) . ?
C1 C15 1.464(5) . ?
C2 C3 1.325(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.492(5) . ?
C4 C5 1.536(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.535(5) . ?
C5 C6 1.544(5) . ?
C6 C7 1.377(5) . ?
C6 C11 1.385(5) . ?
C7 C8 1.390(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.364(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.403(5) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.386(5) . ?
C15 C20 1.390(5) . ?
C16 C17 1.382(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
C1 N1 C2 103.8(3) . . ?
C1 O1 C3 104.8(3) . . ?
C5 O2 H2 109.5 . . ?
C13 O4 C14 116.6(3) . . ?
C10 O5 C12 117.9(3) . . ?
N1 C1 O1 113.8(3) . . ?
N1 C1 C15 128.1(3) . . ?
O1 C1 C15 118.2(3) . . ?
C3 C2 N1 111.1(3) . . ?
C3 C2 H2A 124.5 . . ?
N1 C2 H2A 124.5 . . ?
C2 C3 O1 106.6(3) . . ?
C2 C3 C4 136.5(4) . . ?
O1 C3 C4 116.8(3) . . ?
C3 C4 C5 113.7(3) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O2 C5 C4 106.9(3) . . ?
O2 C5 C13 110.6(3) . . ?
C4 C5 C13 108.5(3) . . ?
O2 C5 C6 111.7(3) . . ?
C4 C5 C6 109.5(3) . . ?
C13 C5 C6 109.5(3) . . ?
C7 C6 C11 119.5(3) . . ?
C7 C6 C5 122.7(3) . . ?
C11 C6 C5 117.8(3) . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 O5 116.3(4) . . ?
C9 C10 C11 119.9(4) . . ?
O5 C10 C11 123.7(4) . . ?
C6 C11 C10 119.9(4) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 123.6(4) . . ?
O3 C13 C5 124.7(3) . . ?
O4 C13 C5 111.7(3) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.1(4) . . ?
C16 C15 C1 121.6(3) . . ?
C20 C15 C1 119.3(3) . . ?
C17 C16 C15 120.2(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 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 O1 0.1(4) . . . . ?
C2 N1 C1 C15 -179.6(3) . . . . ?
C3 O1 C1 N1 0.2(4) . . . . ?
C3 O1 C1 C15 179.9(3) . . . . ?
C1 N1 C2 C3 -0.4(4) . . . . ?
N1 C2 C3 O1 0.5(4) . . . . ?
N1 C2 C3 C4 -175.6(4) . . . . ?
C1 O1 C3 C2 -0.4(4) . . . . ?
C1 O1 C3 C4 176.6(3) . . . . ?
C2 C3 C4 C5 -89.7(5) . . . . ?
O1 C3 C4 C5 94.4(4) . . . . ?
C3 C4 C5 O2 -56.3(4) . . . . ?
C3 C4 C5 C13 63.0(4) . . . . ?
C3 C4 C5 C6 -177.4(3) . . . . ?
O2 C5 C6 C7 151.1(3) . . . . ?
C4 C5 C6 C7 -90.7(4) . . . . ?
C13 C5 C6 C7 28.2(5) . . . . ?
O2 C5 C6 C11 -30.9(4) . . . . ?
C4 C5 C6 C11 87.3(4) . . . . ?
C13 C5 C6 C11 -153.7(3) . . . . ?
C11 C6 C7 C8 2.5(6) . . . . ?
C5 C6 C7 C8 -179.5(4) . . . . ?
C6 C7 C8 C9 -1.2(7) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 O5 -179.6(4) . . . . ?
C8 C9 C10 C11 1.9(7) . . . . ?
C12 O5 C10 C9 175.4(4) . . . . ?
C12 O5 C10 C11 -6.1(6) . . . . ?
C7 C6 C11 C10 -1.7(5) . . . . ?
C5 C6 C11 C10 -179.8(3) . . . . ?
C9 C10 C11 C6 -0.5(6) . . . . ?
O5 C10 C11 C6 -179.0(4) . . . . ?
C14 O4 C13 O3 -2.8(6) . . . . ?
C14 O4 C13 C5 177.8(3) . . . . ?
O2 C5 C13 O3 145.8(4) . . . . ?
C4 C5 C13 O3 28.8(5) . . . . ?
C6 C5 C13 O3 -90.7(4) . . . . ?
O2 C5 C13 O4 -34.8(4) . . . . ?
C4 C5 C13 O4 -151.8(3) . . . . ?
C6 C5 C13 O4 88.7(4) . . . . ?
N1 C1 C15 C16 -164.4(4) . . . . ?
O1 C1 C15 C16 15.9(5) . . . . ?
N1 C1 C15 C20 14.6(6) . . . . ?
O1 C1 C15 C20 -165.0(3) . . . . ?
C20 C15 C16 C17 -0.2(5) . . . . ?
C1 C15 C16 C17 178.8(3) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C17 C18 C19 -2.1(6) . . . . ?
C17 C18 C19 C20 1.1(6) . . . . ?
C18 C19 C20 C15 0.4(6) . . . . ?
C16 C15 C20 C19 -0.8(5) . . . . ?
C1 C15 C20 C19 -179.9(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
O2 H2 N1 0.82 2.15 2.957(4) 168.3 1_455

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 991898'
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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_131104_s3_lww
_audit_creation_date             2013-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h20n2o3br1
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'
Br Br -0.2901 2.4595 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.3897(5)
_cell_length_b                   5.3882(2)
_cell_length_c                   13.3371(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.961(5)
_cell_angle_gamma                90
_cell_volume                     782.90(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9720
_cell_measurement_theta_min      3.1840
_shelx_estimated_absorpt_T_max   0.620
_shelx_estimated_absorpt_T_min   0.505
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3827
_diffrn_reflns_point_group_measured_fraction_full 0.806
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.194
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.6810
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0484930000
_diffrn_orient_matrix_UB_12      -0.0446636000
_diffrn_orient_matrix_UB_13      0.0426230000
_diffrn_orient_matrix_UB_21      0.0058321000
_diffrn_orient_matrix_UB_22      0.1190502000
_diffrn_orient_matrix_UB_23      0.0236895000
_diffrn_orient_matrix_UB_31      -0.0430342000
_diffrn_orient_matrix_UB_32      -0.0342165000
_diffrn_orient_matrix_UB_33      0.0267018000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.450
_reflns_Friedel_fraction_full    0.566
_reflns_Friedel_fraction_max     0.561
_reflns_number_gt                2112
_reflns_number_total             2577
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.024(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0312P)²+0.0087P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.43224(6) 0.05138(14) 0.07633(5) 0.0653(3) Uani 1 1 d . . . . .
O1 O 0.8871(2) 1.0812(8) 0.6737(2) 0.0351(9) Uani 1 1 d . . . . .
O2 O 0.4833(3) 0.9984(7) 0.4281(3) 0.0458(12) Uani 1 1 d . . . . .
O3 O 0.6970(4) 1.2216(7) 0.4865(4) 0.0443(12) Uani 1 1 d . . . . .
H3 H 0.637(7) 1.230(17) 0.502(7) 0.11(4) Uiso 1 1 d . . . . .
N1 N 1.0795(3) 1.0180(12) 0.6738(3) 0.0467(14) Uani 1 1 d . . . . .
C1 C 0.4733(5) 0.3066(11) 0.1780(4) 0.0410(14) Uani 1 1 d . . . . .
C2 C 0.3825(5) 0.4176(11) 0.2116(4) 0.0434(16) Uani 1 1 d . . . . .
H2 H 0.3013 0.3669 0.1849 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4131(4) 0.6044(11) 0.2850(4) 0.0392(16) Uani 1 1 d . . . . .
H3A H 0.3522 0.6781 0.3086 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5350(4) 0.6849(10) 0.3248(4) 0.0302(12) Uani 1 1 d . . . . .
C5 C 0.6241(4) 0.5672(15) 0.2896(4) 0.0330(11) Uani 1 1 d . . . . .
H5 H 0.7057 0.6158 0.3159 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5935(5) 0.3795(12) 0.2162(4) 0.0407(14) Uani 1 1 d . . . . .
H6 H 0.6538 0.3030 0.1928 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5635(4) 0.8921(10) 0.4008(4) 0.0325(13) Uani 1 1 d . . . . .
C8 C 0.6962(4) 0.9788(9) 0.4495(4) 0.0320(14) Uani 1 1 d . . . . .
H8 H 0.7387 0.9761 0.3953 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7630(4) 0.8039(10) 0.5385(4) 0.0335(13) Uani 1 1 d . . . . .
H9A H 0.7129 0.7798 0.5853 0.040 Uiso 1 1 calc R U . . .
H9B H 0.7738 0.6436 0.5092 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8852(4) 0.9028(9) 0.5993(4) 0.0325(13) Uani 1 1 d . . . . .
C11 C 1.0015(5) 0.8649(12) 0.6003(5) 0.0460(16) Uani 1 1 d . . . . .
H11 H 1.0265 0.7520 0.5580 0.055 Uiso 1 1 calc R U . . .
C12 C 1.0082(4) 1.1405(10) 0.7146(4) 0.0341(13) Uani 1 1 d . . . . .
C13 C 1.0405(4) 1.3336(11) 0.7951(4) 0.0345(13) Uani 1 1 d . . . . .
C14 C 1.1624(4) 1.3623(12) 0.8544(4) 0.0434(15) Uani 1 1 d . . . . .
H14 H 1.2217 1.2559 0.8433 0.052 Uiso 1 1 calc R U . . .
C15 C 1.1963(4) 1.5434(16) 0.9283(4) 0.0479(14) Uani 1 1 d . . . . .
H15 H 1.2784 1.5586 0.9670 0.057 Uiso 1 1 calc R U . . .
C16 C 1.1117(6) 1.7036(12) 0.9467(5) 0.0540(17) Uani 1 1 d . . . . .
H16 H 1.1358 1.8286 0.9966 0.065 Uiso 1 1 calc R U . . .
C17 C 0.9883(6) 1.6763(12) 0.8892(5) 0.0561(18) Uani 1 1 d . . . . .
H17 H 0.9294 1.7818 0.9015 0.067 Uiso 1 1 calc R U . . .
C18 C 0.9540(4) 1.4930(11) 0.8142(5) 0.0438(17) Uani 1 1 d . . . . .
H18 H 0.8719 1.4761 0.7761 0.053 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.892(6) . ?
O1 C10 1.378(6) . ?
O1 C12 1.366(5) . ?
O2 C7 1.220(6) . ?
O3 H3 0.77(7) . ?
O3 C8 1.397(7) . ?
N1 C11 1.386(7) . ?
N1 C12 1.284(7) . ?
C1 C2 1.378(8) . ?
C1 C6 1.371(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(7) . ?
C3 H3A 0.9300 . ?
C3 C4 1.403(6) . ?
C4 C5 1.390(7) . ?
C4 C7 1.478(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.534(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.533(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.490(6) . ?
C10 C11 1.335(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.462(7) . ?
C13 C14 1.392(6) . ?
C13 C18 1.386(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.361(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(8) . ?
C18 H18 0.9300 . ?

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
C12 O1 C10 104.6(4) . . ?
C8 O3 H3 103(7) . . ?
C12 N1 C11 104.6(4) . . ?
C2 C1 Br1 119.8(4) . . ?
C6 C1 Br1 119.0(5) . . ?
C6 C1 C2 121.2(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3A 119.6 . . ?
C2 C3 C4 120.8(5) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 C7 119.2(5) . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 C7 122.7(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.5(5) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O2 C7 C4 121.7(4) . . ?
O2 C7 C8 117.5(5) . . ?
C4 C7 C8 120.8(4) . . ?
O3 C8 C7 109.8(4) . . ?
O3 C8 H8 108.7 . . ?
O3 C8 C9 110.6(5) . . ?
C7 C8 H8 108.7 . . ?
C9 C8 C7 110.2(4) . . ?
C9 C8 H8 108.7 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.0(4) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O1 C10 C9 117.2(4) . . ?
C11 C10 O1 107.0(4) . . ?
C11 C10 C9 135.8(5) . . ?
N1 C11 H11 124.9 . . ?
C10 C11 N1 110.2(5) . . ?
C10 C11 H11 124.9 . . ?
O1 C12 C13 117.9(5) . . ?
N1 C12 O1 113.6(5) . . ?
N1 C12 C13 128.5(4) . . ?
C14 C13 C12 119.5(5) . . ?
C18 C13 C12 122.4(4) . . ?
C18 C13 C14 118.1(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(5) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.1(5) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(6) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(5) . . ?
C17 C18 H18 119.6 . . ?

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
Br1 C1 C2 C3 -179.5(4) . . . . ?
Br1 C1 C6 C5 179.3(5) . . . . ?
O1 C10 C11 N1 -0.6(7) . . . . ?
O1 C12 C13 C14 166.3(5) . . . . ?
O1 C12 C13 C18 -14.5(8) . . . . ?
O2 C7 C8 O3 -22.1(7) . . . . ?
O2 C7 C8 C9 100.0(5) . . . . ?
O3 C8 C9 C10 -49.1(6) . . . . ?
N1 C12 C13 C14 -15.5(9) . . . . ?
N1 C12 C13 C18 163.7(6) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C2 C1 C6 C5 0.1(9) . . . . ?
C2 C3 C4 C5 -1.3(8) . . . . ?
C2 C3 C4 C7 177.8(5) . . . . ?
C3 C4 C5 C6 1.1(9) . . . . ?
C3 C4 C7 O2 -1.6(8) . . . . ?
C3 C4 C7 C8 177.5(5) . . . . ?
C4 C5 C6 C1 -0.5(9) . . . . ?
C4 C7 C8 O3 158.8(5) . . . . ?
C4 C7 C8 C9 -79.2(6) . . . . ?
C5 C4 C7 O2 177.5(6) . . . . ?
C5 C4 C7 C8 -3.4(8) . . . . ?
C6 C1 C2 C3 -0.3(8) . . . . ?
C7 C4 C5 C6 -178.0(5) . . . . ?
C7 C8 C9 C10 -170.8(5) . . . . ?
C8 C9 C10 O1 80.0(6) . . . . ?
C8 C9 C10 C11 -98.9(8) . . . . ?
C9 C10 C11 N1 178.4(6) . . . . ?
C10 O1 C12 N1 -0.2(6) . . . . ?
C10 O1 C12 C13 178.3(5) . . . . ?
C11 N1 C12 O1 -0.2(7) . . . . ?
C11 N1 C12 C13 -178.5(5) . . . . ?
C12 O1 C10 C9 -178.7(5) . . . . ?
C12 O1 C10 C11 0.5(6) . . . . ?
C12 N1 C11 C10 0.5(7) . . . . ?
C12 C13 C14 C15 178.5(6) . . . . ?
C12 C13 C18 C17 -178.6(5) . . . . ?
C13 C14 C15 C16 -0.1(10) . . . . ?
C14 C13 C18 C17 0.7(9) . . . . ?
C14 C15 C16 C17 1.0(10) . . . . ?
C15 C16 C17 C18 -1.1(10) . . . . ?
C16 C17 C18 C13 0.3(9) . . . . ?
C18 C13 C14 C15 -0.8(9) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 994240'
