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

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_ep305

_audit_creation_date             2014-02-27T10:35:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.1563(13)
_cell_length_b                   8.2068(17)
_cell_length_c                   14.895(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.888(3)
_cell_angle_gamma                90
_cell_volume                     739.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_number            5755
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2952
_reflns_number_gt                2264
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness 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 > 2σ(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.
;
_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)+(0.0544P)²+0.0274P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2952
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_restrained_S_all      1.324
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.3722(5) 0.1018(4) 0.9607(2) 0.0545(7) Uani 1 1 d . . .
H1 H 0.5031 0.0461 0.9593 0.065 Uiso 1 1 calc R . .
C2 C 0.2064(6) 0.1000(4) 0.8850(2) 0.0679(9) Uani 1 1 d . . .
H2 H 0.2243 0.0413 0.8335 0.082 Uiso 1 1 calc R . .
C3 C 0.0167(6) 0.1835(5) 0.8849(2) 0.0719(10) Uani 1 1 d . . .
H3 H -0.0957 0.1828 0.8335 0.086 Uiso 1 1 calc R . .
C4 C -0.0077(5) 0.2690(4) 0.9612(2) 0.0693(10) Uani 1 1 d . . .
H4 H -0.1376 0.3269 0.961 0.083 Uiso 1 1 calc R . .
C5 C 0.1533(5) 0.2713(4) 1.0373(2) 0.0532(7) Uani 1 1 d . . .
H5 H 0.1333 0.3307 1.0882 0.064 Uiso 1 1 calc R . .
C6 C 0.3486(4) 0.1845(3) 1.03896(18) 0.0435(6) Uani 1 1 d . . .
C7 C 0.5272(5) 0.1828(4) 1.12445(19) 0.0518(7) Uani 1 1 d . . .
H7A H 0.6636 0.2244 1.1096 0.062 Uiso 1 1 calc R . .
H7B H 0.484 0.2549 1.1696 0.062 Uiso 1 1 calc R . .
C8 C 0.5684(4) 0.0137(3) 1.16524(17) 0.0459(6) Uani 1 1 d . . .
H8A H 0.6111 -0.0578 1.1197 0.055 Uiso 1 1 calc R . .
H8B H 0.4312 -0.0276 1.1794 0.055 Uiso 1 1 calc R . .
C9 C 0.7455(4) 0.0070(4) 1.25112(18) 0.0464(6) Uani 1 1 d . . .
H9 H 0.7628 -0.1054 1.2736 0.056 Uiso 1 1 calc R . .
C10 C 0.5602(4) 0.1023(4) 1.38336(17) 0.0477(7) Uani 1 1 d . . .
C11 C 0.6002(5) 0.2538(4) 1.4415(2) 0.0598(8) Uani 1 1 d . . .
H11A H 0.6555 0.2246 1.5048 0.072 Uiso 1 1 calc R . .
H11B H 0.4632 0.3137 1.4383 0.072 Uiso 1 1 calc R . .
C12 C 0.7710(4) 0.3592(3) 1.40514(17) 0.0456(7) Uani 1 1 d . . .
C13 C 0.9921(4) 0.2385(4) 1.28672(18) 0.0455(7) Uani 1 1 d . . .
C14 C 0.9694(4) 0.0748(4) 1.2408(2) 0.0492(7) Uani 1 1 d . . .
H14A H 1.0871 0.0026 1.2695 0.059 Uiso 1 1 calc R . .
H14B H 0.9772 0.0858 1.1767 0.059 Uiso 1 1 calc R . .
C15 C 0.9741(5) 0.3919(5) 1.4767(2) 0.0684(9) Uani 1 1 d . . .
H15A H 1.0324 0.2907 1.5033 0.103 Uiso 1 1 calc R . .
H15B H 0.9358 0.4607 1.5235 0.103 Uiso 1 1 calc R . .
H15C H 1.0837 0.4452 1.449 0.103 Uiso 1 1 calc R . .
C16 C 0.6720(6) 0.5156(5) 1.3628(2) 0.0759(10) Uani 1 1 d . . .
H16A H 0.779 0.5717 1.3349 0.114 Uiso 1 1 calc R . .
H16B H 0.6302 0.5833 1.4093 0.114 Uiso 1 1 calc R . .
H16C H 0.5438 0.4914 1.3172 0.114 Uiso 1 1 calc R . .
N1 N 0.6925(4) 0.1131(3) 1.32274(15) 0.0488(6) Uani 1 1 d . . .
N2 N 0.8260(4) 0.2515(3) 1.33215(16) 0.0509(6) Uani 1 1 d . . .
O1 O 1.1313(3) 0.3426(3) 1.28392(14) 0.0627(6) Uani 1 1 d . . .
O2 O 0.4358(3) -0.0084(3) 1.39009(14) 0.0691(7) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.371(4) . ?
C1 C6 1.380(4) . ?
C1 H1 0.93 . ?
C2 C3 1.354(5) . ?
C2 H2 0.93 . ?
C3 C4 1.369(5) . ?
C3 H3 0.93 . ?
C4 C5 1.357(4) . ?
C4 H4 0.93 . ?
C5 C6 1.394(4) . ?
C5 H5 0.93 . ?
C6 C7 1.517(4) . ?
C7 C8 1.517(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.517(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N1 1.461(4) . ?
C9 C14 1.521(4) . ?
C9 H9 0.98 . ?
C10 O2 1.205(3) . ?
C10 N1 1.328(3) . ?
C10 C11 1.508(4) . ?
C11 C12 1.537(4) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N2 1.489(3) . ?
C12 C15 1.506(4) . ?
C12 C16 1.507(5) . ?
C13 O1 1.217(3) . ?
C13 N2 1.332(3) . ?
C13 C14 1.502(4) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
N1 N2 1.393(3) . ?

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 C1 C6 121.3(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 121.9(2) . . ?
C5 C6 C7 120.4(2) . . ?
C8 C7 C6 112.6(2) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 114.2(2) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C8 111.7(2) . . ?
N1 C9 C14 100.8(2) . . ?
C8 C9 C14 115.0(2) . . ?
N1 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C14 C9 H9 109.7 . . ?
O2 C10 N1 126.0(3) . . ?
O2 C10 C11 127.7(3) . . ?
N1 C10 C11 106.3(2) . . ?
C10 C11 C12 108.1(2) . . ?
C10 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N2 C12 C15 110.5(2) . . ?
N2 C12 C16 109.3(2) . . ?
C15 C12 C16 111.1(3) . . ?
N2 C12 C11 100.8(2) . . ?
C15 C12 C11 112.5(3) . . ?
C16 C12 C11 112.2(3) . . ?
O1 C13 N2 125.0(3) . . ?
O1 C13 C14 128.2(2) . . ?
N2 C13 C14 106.8(2) . . ?
C13 C14 C9 106.8(2) . . ?
C13 C14 H14A 110.4 . . ?
C9 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
C9 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 N1 N2 114.3(2) . . ?
C10 N1 C9 135.0(2) . . ?
N2 N1 C9 110.49(19) . . ?
C13 N2 N1 112.2(2) . . ?
C13 N2 C12 136.1(2) . . ?
N1 N2 C12 110.24(19) . . ?

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 1.6(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C2 C1 C6 C5 -2.3(4) . . . . ?
C2 C1 C6 C7 177.8(3) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C1 C6 C7 C8 -63.4(4) . . . . ?
C5 C6 C7 C8 116.8(3) . . . . ?
C6 C7 C8 C9 -179.8(2) . . . . ?
C7 C8 C9 N1 58.1(3) . . . . ?
C7 C8 C9 C14 -56.0(3) . . . . ?
O2 C10 C11 C12 -179.1(3) . . . . ?
N1 C10 C11 C12 1.6(3) . . . . ?
C10 C11 C12 N2 -3.8(3) . . . . ?
C10 C11 C12 C15 -121.4(3) . . . . ?
C10 C11 C12 C16 112.4(3) . . . . ?
O1 C13 C14 C9 -169.3(3) . . . . ?
N2 C13 C14 C9 10.1(3) . . . . ?
N1 C9 C14 C13 -15.6(3) . . . . ?
C8 C9 C14 C13 104.7(3) . . . . ?
O2 C10 N1 N2 -177.7(3) . . . . ?
C11 C10 N1 N2 1.6(3) . . . . ?
O2 C10 N1 C9 -3.3(5) . . . . ?
C11 C10 N1 C9 176.0(3) . . . . ?
C8 C9 N1 C10 79.4(4) . . . . ?
C14 C9 N1 C10 -158.0(3) . . . . ?
C8 C9 N1 N2 -106.2(3) . . . . ?
C14 C9 N1 N2 16.5(3) . . . . ?
O1 C13 N2 N1 179.9(3) . . . . ?
C14 C13 N2 N1 0.5(3) . . . . ?
O1 C13 N2 C12 -15.7(5) . . . . ?
C14 C13 N2 C12 164.9(3) . . . . ?
C10 N1 N2 C13 164.2(2) . . . . ?
C9 N1 N2 C13 -11.5(3) . . . . ?
C10 N1 N2 C12 -4.4(3) . . . . ?
C9 N1 N2 C12 179.9(2) . . . . ?
C15 C12 N2 C13 -40.8(4) . . . . ?
C16 C12 N2 C13 81.8(4) . . . . ?
C11 C12 N2 C13 -159.9(3) . . . . ?
C15 C12 N2 N1 123.9(3) . . . . ?
C16 C12 N2 N1 -113.5(3) . . . . ?
C11 C12 N2 N1 4.8(3) . . . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 992848'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_cb719

_audit_creation_date             2014-02-19T11:28:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H19 Br1 N2 O2'
_chemical_formula_sum            'C16 H19 Br N2 O2'
_chemical_formula_weight         351.24
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.137(2)
_cell_length_b                   8.934(3)
_cell_length_c                   14.270(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.976(6)
_cell_angle_gamma                90
_cell_volume                     770.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.673
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_number            6180
_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         1.45
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3117
_reflns_number_gt                2444
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness 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 > 2σ(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.
;
_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)+(0.0310P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.086
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   0.93
_refine_ls_restrained_S_all      0.929
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(10)
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 1.3678(6) 0.9251(5) 0.9577(3) 0.0529(9) Uani 1 1 d . . .
H1 H 1.4938 0.9818 0.9556 0.063 Uiso 1 1 calc R . .
C2 C 1.1979(7) 0.9255(5) 0.8799(3) 0.0559(10) Uani 1 1 d . . .
H2 H 1.2103 0.9825 0.8266 0.067 Uiso 1 1 calc R . .
C3 C 1.0127(5) 0.8423(6) 0.8816(2) 0.0448(7) Uani 1 1 d . . .
C4 C 0.9981(7) 0.7535(4) 0.9598(3) 0.0483(9) Uani 1 1 d . . .
H4 H 0.8748 0.6931 0.9603 0.058 Uiso 1 1 calc R . .
C5 C 1.1681(6) 0.7553(4) 1.0371(2) 0.0460(9) Uani 1 1 d . . .
H5 H 1.1572 0.6965 1.0899 0.055 Uiso 1 1 calc R . .
C6 C 1.3546(5) 0.8429(6) 1.03775(18) 0.0391(6) Uani 1 1 d . . .
C7 C 1.5350(5) 0.8484(6) 1.1242(2) 0.0443(7) Uani 1 1 d . . .
H7A H 1.6712 0.8106 1.1073 0.053 Uiso 1 1 calc R . .
H7B H 1.4951 0.7837 1.1731 0.053 Uiso 1 1 calc R . .
C8 C 1.5740(6) 1.0051(4) 1.1635(2) 0.0392(8) Uani 1 1 d . . .
H8A H 1.4364 1.0431 1.1789 0.047 Uiso 1 1 calc R . .
H8B H 1.6149 1.069 1.1144 0.047 Uiso 1 1 calc R . .
C9 C 1.7527(5) 1.0164(4) 1.2519(2) 0.0365(8) Uani 1 1 d . . .
H9 H 1.766 1.1208 1.2734 0.044 Uiso 1 1 calc R . .
C10 C 1.9818(5) 0.9582(4) 1.2391(3) 0.0425(8) Uani 1 1 d . . .
H10A H 1.9875 0.9438 1.1722 0.051 Uiso 1 1 calc R . .
H10B H 2.0965 1.0285 1.2655 0.051 Uiso 1 1 calc R . .
C11 C 2.0130(5) 0.8109(4) 1.2917(2) 0.0379(9) Uani 1 1 d . . .
C12 C 1.5720(5) 0.9316(4) 1.3940(2) 0.0383(8) Uani 1 1 d . . .
C13 C 1.6239(6) 0.7988(4) 1.4572(3) 0.0521(11) Uani 1 1 d . . .
H13A H 1.4902 0.7417 1.459 0.063 Uiso 1 1 calc R . .
H13B H 1.6838 0.831 1.5214 0.063 Uiso 1 1 calc R . .
C14 C 1.7937(5) 0.7010(4) 1.4182(2) 0.0366(7) Uani 1 1 d . . .
C15 C 1.9942(7) 0.6715(5) 1.4916(3) 0.0659(12) Uani 1 1 d . . .
H15A H 2.0954 0.6094 1.4648 0.099 Uiso 1 1 calc R . .
H15B H 1.9512 0.6214 1.5451 0.099 Uiso 1 1 calc R . .
H15C H 2.0647 0.7646 1.5121 0.099 Uiso 1 1 calc R . .
C16 C 1.6922(8) 0.5583(5) 1.3751(3) 0.0607(11) Uani 1 1 d . . .
H16A H 1.5683 0.5815 1.3264 0.091 Uiso 1 1 calc R . .
H16B H 1.6431 0.499 1.4236 0.091 Uiso 1 1 calc R . .
H16C H 1.8003 0.5033 1.3479 0.091 Uiso 1 1 calc R . .
Br01 Br 0.78253(6) 0.84256(6) 0.77526(2) 0.06661(16) Uani 1 1 d . . .
N1 N 1.8485(5) 0.7998(3) 1.3426(2) 0.0442(8) Uani 1 1 d . . .
N2 N 1.7069(5) 0.9220(3) 1.32937(19) 0.0390(6) Uani 1 1 d . . .
O1 O 1.4383(4) 1.0315(3) 1.39762(18) 0.0538(6) Uani 1 1 d . . .
O2 O 2.1566(4) 0.7184(3) 1.2890(2) 0.0573(7) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.372(5) . ?
C1 C2 1.385(5) . ?
C1 H1 0.93 . ?
C2 C3 1.362(5) . ?
C2 H2 0.93 . ?
C3 C4 1.385(5) . ?
C3 Br01 1.886(3) . ?
C4 C5 1.381(5) . ?
C4 H4 0.93 . ?
C5 C6 1.385(6) . ?
C5 H5 0.93 . ?
C6 C7 1.509(4) . ?
C7 C8 1.512(6) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.524(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.456(4) . ?
C9 C10 1.540(5) . ?
C9 H9 0.98 . ?
C10 C11 1.510(5) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O2 1.214(4) . ?
C11 N1 1.346(4) . ?
C12 O1 1.219(4) . ?
C12 N2 1.345(4) . ?
C12 C13 1.491(5) . ?
C13 C14 1.536(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 N1 1.476(4) . ?
C14 C15 1.495(5) . ?
C14 C16 1.503(5) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
N1 N2 1.388(4) . ?

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 C1 C2 121.6(3) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120 . . ?
C1 C2 H2 120 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 Br01 119.7(3) . . ?
C4 C3 Br01 120.3(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.7(3) . . ?
C1 C6 C7 121.5(4) . . ?
C5 C6 C7 120.8(3) . . ?
C6 C7 C8 112.4(4) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 114.4(3) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C8 112.6(3) . . ?
N2 C9 C10 101.2(3) . . ?
C8 C9 C10 114.9(3) . . ?
N2 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C11 C10 C9 106.0(3) . . ?
C11 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
O2 C11 N1 125.7(3) . . ?
O2 C11 C10 127.4(3) . . ?
N1 C11 C10 106.9(3) . . ?
O1 C12 N2 125.0(3) . . ?
O1 C12 C13 129.2(3) . . ?
N2 C12 C13 105.8(3) . . ?
C12 C13 C14 108.7(3) . . ?
C12 C13 H13A 110 . . ?
C14 C13 H13A 110 . . ?
C12 C13 H13B 110 . . ?
C14 C13 H13B 110 . . ?
H13A C13 H13B 108.3 . . ?
N1 C14 C15 110.7(3) . . ?
N1 C14 C16 109.8(3) . . ?
C15 C14 C16 111.7(3) . . ?
N1 C14 C13 100.4(2) . . ?
C15 C14 C13 112.0(3) . . ?
C16 C14 C13 111.8(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 N1 N2 112.2(3) . . ?
C11 N1 C14 136.5(3) . . ?
N2 N1 C14 110.7(2) . . ?
C12 N2 N1 113.7(3) . . ?
C12 N2 C9 135.0(3) . . ?
N1 N2 C9 111.1(2) . . ?

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 -0.4(6) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
C1 C2 C3 Br01 -179.7(3) . . . . ?
C2 C3 C4 C5 2.8(6) . . . . ?
Br01 C3 C4 C5 -179.8(3) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C2 C1 C6 C5 2.3(6) . . . . ?
C2 C1 C6 C7 -177.0(4) . . . . ?
C4 C5 C6 C1 -1.7(6) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C1 C6 C7 C8 58.4(5) . . . . ?
C5 C6 C7 C8 -120.9(5) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 N2 -57.5(4) . . . . ?
C7 C8 C9 C10 57.6(4) . . . . ?
N2 C9 C10 C11 15.0(3) . . . . ?
C8 C9 C10 C11 -106.5(3) . . . . ?
C9 C10 C11 O2 169.2(3) . . . . ?
C9 C10 C11 N1 -10.4(4) . . . . ?
O1 C12 C13 C14 176.1(4) . . . . ?
N2 C12 C13 C14 -4.4(4) . . . . ?
C12 C13 C14 N1 7.9(4) . . . . ?
C12 C13 C14 C15 125.4(3) . . . . ?
C12 C13 C14 C16 -108.5(4) . . . . ?
O2 C11 N1 N2 -178.6(3) . . . . ?
C10 C11 N1 N2 1.0(4) . . . . ?
O2 C11 N1 C14 10.9(7) . . . . ?
C10 C11 N1 C14 -169.5(4) . . . . ?
C15 C14 N1 C11 43.4(6) . . . . ?
C16 C14 N1 C11 -80.4(5) . . . . ?
C13 C14 N1 C11 161.8(4) . . . . ?
C15 C14 N1 N2 -127.2(3) . . . . ?
C16 C14 N1 N2 109.0(3) . . . . ?
C13 C14 N1 N2 -8.8(4) . . . . ?
O1 C12 N2 N1 178.1(3) . . . . ?
C13 C12 N2 N1 -1.4(4) . . . . ?
O1 C12 N2 C9 3.8(6) . . . . ?
C13 C12 N2 C9 -175.7(4) . . . . ?
C11 N1 N2 C12 -166.0(3) . . . . ?
C14 N1 N2 C12 7.1(4) . . . . ?
C11 N1 N2 C9 9.7(4) . . . . ?
C14 N1 N2 C9 -177.3(3) . . . . ?
C8 C9 N2 C12 -77.6(5) . . . . ?
C10 C9 N2 C12 159.2(4) . . . . ?
C8 C9 N2 N1 108.0(3) . . . . ?
C10 C9 N2 N1 -15.1(3) . . . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 992846'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_cb745


_diffrn_measurement_method       'theta scans'
#Added by publCIF




_diffrn_radiation_source         'X-Ray, Mo'
#Added by publCIF




_diffrn_measurement_device_type  'SMART APEX'
#Added by publCIF




_computing_structure_solution    SHELXS97
#Added by publCIF




_computing_data_reduction        SAINT
#Added by publCIF




_computing_cell_refinement       SMART
#Added by publCIF




_computing_data_collection       'SMART APEX'
#Added by publCIF



_audit_creation_date             2014-03-14T13:18:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N2 O2'
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8127(7)
_cell_length_b                   9.5156(12)
_cell_length_c                   11.5873(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.442(2)
_cell_angle_gamma                90
_cell_volume                     623.35(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_special_details           ?

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_number            4975
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2514
_reflns_number_gt                2321
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness 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 > 2σ(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.
;
_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)+(0.0589P)²+0.0316P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2514
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(12)
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8503(3) 0.22567(17) 1.10490(13) 0.0470(3) Uani 1 1 d . . .
H1 H 0.7025 0.2065 1.0561 0.056 Uiso 1 1 calc R . .
C2 C 0.9092(3) 0.1708(2) 1.21872(14) 0.0551(4) Uani 1 1 d . . .
H2 H 0.801 0.1158 1.2463 0.066 Uiso 1 1 calc R . .
C3 C 1.1271(3) 0.1978(2) 1.29038(14) 0.0588(5) Uani 1 1 d . . .
H3 H 1.1674 0.16 1.3665 0.071 Uiso 1 1 calc R . .
C4 C 1.2870(3) 0.2803(2) 1.25077(14) 0.0580(5) Uani 1 1 d . . .
H4 H 1.4352 0.298 1.2998 0.07 Uiso 1 1 calc R . .
C5 C 1.2271(3) 0.33718(19) 1.13766(14) 0.0500(4) Uani 1 1 d . . .
H5 H 1.334 0.3949 1.1116 0.06 Uiso 1 1 calc R . .
C6 C 1.0087(2) 0.30856(15) 1.06298(12) 0.0401(3) Uani 1 1 d . . .
C7 C 0.9512(3) 0.36675(17) 0.93826(13) 0.0438(3) Uani 1 1 d . . .
H7 H 1.0664 0.4402 0.9329 0.053 Uiso 1 1 calc R . .
C8 C 0.7012(3) 0.42668(18) 0.89274(13) 0.0478(4) Uani 1 1 d . . .
H8A H 0.5945 0.3898 0.9384 0.057 Uiso 1 1 calc R . .
H8B H 0.7031 0.5284 0.8985 0.057 Uiso 1 1 calc R . .
C9 C 0.6248(3) 0.38076(17) 0.76452(13) 0.0443(3) Uani 1 1 d . . .
C10 C 0.8285(2) 0.21306(19) 0.64252(12) 0.0455(4) Uani 1 1 d . . .
C11 C 1.0462(3) 0.1246(2) 0.70023(15) 0.0538(4) Uani 1 1 d . . .
H11A H 1.0034 0.0262 0.7018 0.065 Uiso 1 1 calc R . .
H11B H 1.1679 0.1338 0.6559 0.065 Uiso 1 1 calc R . .
C12 C 1.1346(2) 0.17962(17) 0.82509(12) 0.0429(3) Uani 1 1 d . . .
C13 C 0.8858(4) 0.3262(2) 0.56095(17) 0.0684(5) Uani 1 1 d . . .
H13A H 0.7517 0.3871 0.5361 0.103 Uiso 1 1 calc R . .
H13B H 0.9228 0.283 0.4926 0.103 Uiso 1 1 calc R . .
H13C H 1.0192 0.38 0.6026 0.103 Uiso 1 1 calc R . .
C14 C 0.6198(3) 0.1250(2) 0.58121(19) 0.0687(6) Uani 1 1 d . . .
H14A H 0.5798 0.0602 0.637 0.103 Uiso 1 1 calc R . .
H14B H 0.6597 0.0737 0.5172 0.103 Uiso 1 1 calc R . .
H14C H 0.487 0.185 0.5504 0.103 Uiso 1 1 calc R . .
N1 N 0.7766(2) 0.28140(17) 0.74797(10) 0.0524(4) Uani 1 1 d . . .
N2 N 0.9596(2) 0.25840(16) 0.84870(10) 0.0475(3) Uani 1 1 d . . .
O1 O 0.4554(2) 0.42200(15) 0.68976(10) 0.0605(3) Uani 1 1 d . . .
O2 O 1.3227(2) 0.15581(15) 0.89321(11) 0.0595(3) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.383(2) . ?
C1 C2 1.385(2) . ?
C1 H1 0.93 . ?
C2 C3 1.368(3) . ?
C2 H2 0.93 . ?
C3 C4 1.375(3) . ?
C3 H3 0.93 . ?
C4 C5 1.385(2) . ?
C4 H4 0.93 . ?
C5 C6 1.387(2) . ?
C5 H5 0.93 . ?
C6 C7 1.5107(18) . ?
C7 N2 1.472(2) . ?
C7 C8 1.536(2) . ?
C7 H7 0.98 . ?
C8 C9 1.513(2) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 O1 1.2156(18) . ?
C9 N1 1.337(2) . ?
C10 N1 1.4759(18) . ?
C10 C14 1.509(2) . ?
C10 C13 1.520(3) . ?
C10 C11 1.537(2) . ?
C11 C12 1.512(2) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 O2 1.2121(17) . ?
C12 N2 1.3416(19) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
N1 N2 1.4017(15) . ?

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 C1 C2 120.79(15) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 119.75(17) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.47(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.88(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.39(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.70(14) . . ?
C1 C6 C7 121.84(13) . . ?
C5 C6 C7 119.45(14) . . ?
N2 C7 C6 112.43(12) . . ?
N2 C7 C8 101.66(11) . . ?
C6 C7 C8 116.49(13) . . ?
N2 C7 H7 108.6 . . ?
C6 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C9 C8 C7 105.56(13) . . ?
C9 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.8 . . ?
O1 C9 N1 125.34(14) . . ?
O1 C9 C8 127.64(15) . . ?
N1 C9 C8 106.99(13) . . ?
N1 C10 C14 109.74(14) . . ?
N1 C10 C13 108.61(15) . . ?
C14 C10 C13 111.67(15) . . ?
N1 C10 C11 100.78(11) . . ?
C14 C10 C11 113.01(15) . . ?
C13 C10 C11 112.39(14) . . ?
C12 C11 C10 106.80(13) . . ?
C12 C11 H11A 110.4 . . ?
C10 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
C10 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
O2 C12 N2 125.70(14) . . ?
O2 C12 C11 127.81(14) . . ?
N2 C12 C11 106.47(12) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 N1 N2 112.92(12) . . ?
C9 N1 C10 134.34(13) . . ?
N2 N1 C10 111.03(11) . . ?
C12 N2 N1 112.46(11) . . ?
C12 N2 C7 133.35(13) . . ?
N1 N2 C7 109.53(12) . . ?

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 -0.5(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 178.47(15) . . . . ?
C4 C5 C6 C1 1.8(2) . . . . ?
C4 C5 C6 C7 -177.46(15) . . . . ?
C1 C6 C7 N2 -73.80(18) . . . . ?
C5 C6 C7 N2 105.41(15) . . . . ?
C1 C6 C7 C8 42.9(2) . . . . ?
C5 C6 C7 C8 -137.85(15) . . . . ?
N2 C7 C8 C9 -17.72(16) . . . . ?
C6 C7 C8 C9 -140.27(13) . . . . ?
C7 C8 C9 O1 -167.94(16) . . . . ?
C7 C8 C9 N1 13.73(18) . . . . ?
N1 C10 C11 C12 -14.73(17) . . . . ?
C14 C10 C11 C12 -131.76(16) . . . . ?
C13 C10 C11 C12 100.73(17) . . . . ?
C10 C11 C12 O2 -166.45(15) . . . . ?
C10 C11 C12 N2 15.34(18) . . . . ?
O1 C9 N1 N2 178.05(16) . . . . ?
C8 C9 N1 N2 -3.58(18) . . . . ?
O1 C9 N1 C10 14.7(3) . . . . ?
C8 C9 N1 C10 -166.94(17) . . . . ?
C14 C10 N1 C9 -67.2(2) . . . . ?
C13 C10 N1 C9 55.1(2) . . . . ?
C11 C10 N1 C9 173.38(18) . . . . ?
C14 C10 N1 N2 129.21(16) . . . . ?
C13 C10 N1 N2 -108.45(16) . . . . ?
C11 C10 N1 N2 9.80(18) . . . . ?
O2 C12 N2 N1 172.37(16) . . . . ?
C11 C12 N2 N1 -9.37(19) . . . . ?
O2 C12 N2 C7 19.8(3) . . . . ?
C11 C12 N2 C7 -161.95(16) . . . . ?
C9 N1 N2 C12 -167.87(14) . . . . ?
C10 N1 N2 C12 -0.55(19) . . . . ?
C9 N1 N2 C7 -8.69(18) . . . . ?
C10 N1 N2 C7 158.64(13) . . . . ?
C6 C7 N2 C12 -65.3(2) . . . . ?
C8 C7 N2 C12 169.44(16) . . . . ?
C6 C7 N2 N1 141.58(13) . . . . ?
C8 C7 N2 N1 16.28(15) . . . . ?

# END of CIF

_database_code_depnum_ccdc_archive 'CCDC 993565'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_cb732b

_audit_creation_date             2014-03-04T17:38:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H19 Br1 N2 O2'
_chemical_formula_sum            'C20 H19 Br N2 O2'
_chemical_formula_weight         399.28
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.560(3)
_cell_length_b                   16.644(7)
_cell_length_c                   33.009(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3604(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_number            26773
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_full        26.45
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3710
_reflns_number_gt                1986
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness 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 > 2σ(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.
;
_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)+(0.0782P)²+3.7276P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.187
_refine_ls_wR_factor_gt          0.1575
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.5100(13) 0.6462(6) 0.4790(2) 0.134(3) Uani 1 1 d . A .
H1 H 0.6412 0.6645 0.4737 0.16 Uiso 1 1 calc R . .
C2 C 0.3960(13) 0.6116(5) 0.44854(18) 0.104(2) Uani 1 1 d . . .
H2 H 0.4531 0.6041 0.423 0.125 Uiso 1 1 calc R . .
C3 C 0.2022(11) 0.5887(3) 0.45563(16) 0.0777(16) Uani 1 1 d . . .
C4 C 0.1162(12) 0.5977(4) 0.49282(19) 0.104(2) Uani 1 1 d . . .
H4 H -0.0185 0.5826 0.4973 0.125 Uiso 1 1 calc R . .
C5 C 0.2309(14) 0.6292(5) 0.52366(18) 0.149(4) Uani 1 1 d . A .
H5 H 0.1736 0.6343 0.5493 0.178 Uiso 1 1 calc R . .
C6 C 0.4282(16) 0.6536(7) 0.51759(19) 0.165(4) Uani 1 1 d . . .
C7 C 0.504(2) 0.7136(7) 0.5514(4) 0.094(5) Uani 0.624(18) 1 d P A 1
H7A H 0.6083 0.7495 0.5411 0.112 Uiso 0.624(18) 1 calc PR A 1
H7B H 0.3922 0.7451 0.5623 0.112 Uiso 0.624(18) 1 calc PR A 1
C8 C 0.5856(19) 0.6595(9) 0.5814(4) 0.072(3) Uani 0.624(18) 1 d P A 1
H8A H 0.698 0.629 0.57 0.086 Uiso 0.624(18) 1 calc PR A 1
H8B H 0.4811 0.622 0.5901 0.086 Uiso 0.624(18) 1 calc PR A 1
C7A C 0.623(2) 0.6564(11) 0.5507(5) 0.062(6) Uani 0.376(18) 1 d P A 2
H7A1 H 0.6668 0.603 0.5586 0.074 Uiso 0.376(18) 1 calc PR A 2
H7A2 H 0.7381 0.6865 0.5403 0.074 Uiso 0.376(18) 1 calc PR A 2
C8A C 0.515(3) 0.7009(12) 0.5855(4) 0.046(4) Uani 0.376(18) 1 d P A 2
H8A1 H 0.4654 0.7526 0.5761 0.055 Uiso 0.376(18) 1 calc PR A 2
H8A2 H 0.3987 0.6698 0.5948 0.055 Uiso 0.376(18) 1 calc PR A 2
C9 C 0.6647(8) 0.7127(3) 0.61985(14) 0.0675(14) Uani 1 1 d . . .
H9 H 0.7648 0.7529 0.6112 0.081 Uiso 1 1 calc R A 1
C10 C 0.5162(8) 0.7486(3) 0.65048(17) 0.0717(15) Uani 1 1 d . A .
H10A H 0.5642 0.8006 0.6596 0.086 Uiso 1 1 calc R . .
H10B H 0.3826 0.7553 0.6384 0.086 Uiso 1 1 calc R . .
C11 C 0.5059(7) 0.6906(3) 0.68548(15) 0.0526(11) Uani 1 1 d . . .
C12 C 0.7422(7) 0.5741(2) 0.70289(12) 0.0488(11) Uani 1 1 d . . .
H12 H 0.7327 0.5908 0.7313 0.059 Uiso 1 1 calc R A .
C13 C 0.9639(7) 0.5821(3) 0.68840(15) 0.0598(12) Uani 1 1 d . A .
H13A H 1.0445 0.6112 0.7082 0.072 Uiso 1 1 calc R . .
H13B H 1.0242 0.5295 0.6844 0.072 Uiso 1 1 calc R . .
C14 C 0.9558(8) 0.6273(3) 0.64929(15) 0.0589(13) Uani 1 1 d . . .
C15 C 0.6510(6) 0.4913(2) 0.69814(12) 0.0459(10) Uani 1 1 d . A .
C16 C 0.7233(7) 0.4299(3) 0.72230(15) 0.0584(12) Uani 1 1 d . . .
H16 H 0.8277 0.44 0.7407 0.07 Uiso 1 1 calc R A .
C17 C 0.6424(8) 0.3542(3) 0.71943(16) 0.0669(14) Uani 1 1 d . A .
H17 H 0.6906 0.3134 0.7361 0.08 Uiso 1 1 calc R . .
C18 C 0.4905(8) 0.3385(3) 0.69198(18) 0.0713(15) Uani 1 1 d . . .
H18 H 0.436 0.2871 0.69 0.086 Uiso 1 1 calc R A .
C19 C 0.4202(8) 0.3981(3) 0.66784(16) 0.0738(15) Uani 1 1 d . A .
H19 H 0.3187 0.3872 0.649 0.089 Uiso 1 1 calc R . .
C20 C 0.4979(7) 0.4750(3) 0.67096(15) 0.0632(13) Uani 1 1 d . . .
H20 H 0.4464 0.5158 0.6546 0.076 Uiso 1 1 calc R A .
Br1 Br 0.04727(14) 0.54728(4) 0.41282(2) 0.1122(4) Uani 1 1 d . . .
N1 N 0.6397(6) 0.6326(2) 0.67747(11) 0.0552(10) Uani 1 1 d . A .
N2 N 0.7619(6) 0.6495(2) 0.64331(10) 0.0580(10) Uani 1 1 d . A .
O1 O 0.3949(5) 0.6922(2) 0.71483(10) 0.0681(9) Uani 1 1 d . A .
O2 O 1.0963(5) 0.6420(3) 0.62634(11) 0.0857(12) Uani 1 1 d . A .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.379(10) . ?
C1 C6 1.388(10) . ?
C1 H1 0.93 . ?
C2 C3 1.348(9) . ?
C2 H2 0.93 . ?
C3 C4 1.359(8) . ?
C3 Br1 1.872(5) . ?
C4 C5 1.371(9) . ?
C4 H4 0.93 . ?
C5 C6 1.370(11) . ?
C5 H5 0.93 . ?
C6 C7 1.579(13) . ?
C6 C7A 1.681(17) . ?
C7 C8 1.44(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.633(13) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C7A C8A 1.54(3) . ?
C7A H7A1 0.97 . ?
C7A H7A2 0.97 . ?
C8A C9 1.514(14) . ?
C8A H8A1 0.97 . ?
C8A H8A2 0.97 . ?
C9 N2 1.454(6) . ?
C9 C10 1.525(7) . ?
C9 H9 0.98 . ?
C10 C11 1.507(7) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O1 1.212(5) . ?
C11 N1 1.331(6) . ?
C12 N1 1.451(5) . ?
C12 C15 1.511(6) . ?
C12 C13 1.537(6) . ?
C12 H12 0.98 . ?
C13 C14 1.495(7) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 O2 1.217(5) . ?
C14 N2 1.339(6) . ?
C15 C20 1.374(6) . ?
C15 C16 1.380(6) . ?
C16 C17 1.371(7) . ?
C16 H16 0.93 . ?
C17 C18 1.372(7) . ?
C17 H17 0.93 . ?
C18 C19 1.354(7) . ?
C18 H18 0.93 . ?
C19 C20 1.382(7) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
N1 N2 1.412(5) . ?

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 C1 C6 119.8(7) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.1(6) . . ?
C2 C3 Br1 119.0(5) . . ?
C4 C3 Br1 119.8(5) . . ?
C3 C4 C5 119.0(7) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.5(7) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 118.3(7) . . ?
C5 C6 C7 112.4(9) . . ?
C1 C6 C7 125.7(8) . . ?
C5 C6 C7A 129.1(8) . . ?
C1 C6 C7A 107.8(9) . . ?
C7 C6 C7A 44.2(6) . . ?
C8 C7 C6 101.9(11) . . ?
C8 C7 H7A 111.4 . . ?
C6 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.2 . . ?
C7 C8 C9 108.2(11) . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8A C7A C6 98.5(12) . . ?
C8A C7A H7A1 112.1 . . ?
C6 C7A H7A1 112.1 . . ?
C8A C7A H7A2 112.1 . . ?
C6 C7A H7A2 112.1 . . ?
H7A1 C7A H7A2 109.7 . . ?
C9 C8A C7A 108.7(14) . . ?
C9 C8A H8A1 109.9 . . ?
C7A C8A H8A1 109.9 . . ?
C9 C8A H8A2 109.9 . . ?
C7A C8A H8A2 109.9 . . ?
H8A1 C8A H8A2 108.3 . . ?
N2 C9 C8A 126.2(9) . . ?
N2 C9 C10 102.1(4) . . ?
C8A C9 C10 97.6(8) . . ?
N2 C9 C8 99.3(6) . . ?
C8A C9 C8 30.8(5) . . ?
C10 C9 C8 121.7(6) . . ?
N2 C9 H9 110.8 . . ?
C8A C9 H9 107.8 . . ?
C10 C9 H9 110.8 . . ?
C8 C9 H9 110.8 . . ?
C11 C10 C9 106.6(4) . . ?
C11 C10 H10A 110.4 . . ?
C9 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
O1 C11 N1 124.8(4) . . ?
O1 C11 C10 128.7(5) . . ?
N1 C11 C10 106.4(4) . . ?
N1 C12 C15 111.7(4) . . ?
N1 C12 C13 101.5(3) . . ?
C15 C12 C13 115.0(4) . . ?
N1 C12 H12 109.5 . . ?
C15 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
C14 C13 C12 106.2(4) . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
O2 C14 N2 124.9(5) . . ?
O2 C14 C13 127.7(5) . . ?
N2 C14 C13 107.4(4) . . ?
C20 C15 C16 118.9(4) . . ?
C20 C15 C12 122.5(4) . . ?
C16 C15 C12 118.6(4) . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.1(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.0(5) . . ?
C15 C20 H20 120 . . ?
C19 C20 H20 120 . . ?
C11 N1 N2 112.9(4) . . ?
C11 N1 C12 132.6(4) . . ?
N2 N1 C12 109.4(3) . . ?
C14 N2 N1 111.5(4) . . ?
C14 N2 C9 134.0(4) . . ?
N1 N2 C9 108.7(4) . . ?

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 3.3(14) . . . . ?
C1 C2 C3 C4 -1.2(11) . . . . ?
C1 C2 C3 Br1 176.6(6) . . . . ?
C2 C3 C4 C5 -1.2(11) . . . . ?
Br1 C3 C4 C5 -179.0(6) . . . . ?
C3 C4 C5 C6 1.5(15) . . . . ?
C4 C5 C6 C1 0.6(18) . . . . ?
C4 C5 C6 C7 160.2(9) . . . . ?
C4 C5 C6 C7A -151.4(12) . . . . ?
C2 C1 C6 C5 -3.0(17) . . . . ?
C2 C1 C6 C7 -159.7(10) . . . . ?
C2 C1 C6 C7A 154.5(10) . . . . ?
C5 C6 C7 C8 89.1(13) . . . . ?
C1 C6 C7 C8 -113.0(14) . . . . ?
C7A C6 C7 C8 -34.5(9) . . . . ?
C6 C7 C8 C9 -178.0(8) . . . . ?
C5 C6 C7A C8A -49.8(19) . . . . ?
C1 C6 C7A C8A 156.0(12) . . . . ?
C7 C6 C7A C8A 32.7(10) . . . . ?
C6 C7A C8A C9 -178.9(10) . . . . ?
C7A C8A C9 N2 -63.4(14) . . . . ?
C7A C8A C9 C10 -174.5(12) . . . . ?
C7A C8A C9 C8 -30.3(14) . . . . ?
C7 C8 C9 N2 -173.1(10) . . . . ?
C7 C8 C9 C8A 33.5(15) . . . . ?
C7 C8 C9 C10 76.4(11) . . . . ?
N2 C9 C10 C11 -13.1(5) . . . . ?
C8A C9 C10 C11 116.5(8) . . . . ?
C8 C9 C10 C11 95.9(7) . . . . ?
C9 C10 C11 O1 -173.5(5) . . . . ?
C9 C10 C11 N1 3.7(5) . . . . ?
N1 C12 C13 C14 -14.9(5) . . . . ?
C15 C12 C13 C14 105.8(4) . . . . ?
C12 C13 C14 O2 -174.7(5) . . . . ?
C12 C13 C14 N2 5.1(5) . . . . ?
N1 C12 C15 C20 3.6(6) . . . . ?
C13 C12 C15 C20 -111.4(5) . . . . ?
N1 C12 C15 C16 -175.9(4) . . . . ?
C13 C12 C15 C16 69.1(5) . . . . ?
C20 C15 C16 C17 -0.5(7) . . . . ?
C12 C15 C16 C17 178.9(4) . . . . ?
C15 C16 C17 C18 1.0(8) . . . . ?
C16 C17 C18 C19 -0.3(8) . . . . ?
C17 C18 C19 C20 -1.0(8) . . . . ?
C16 C15 C20 C19 -0.6(7) . . . . ?
C12 C15 C20 C19 179.9(4) . . . . ?
C18 C19 C20 C15 1.4(8) . . . . ?
O1 C11 N1 N2 -174.6(4) . . . . ?
C10 C11 N1 N2 8.0(5) . . . . ?
O1 C11 N1 C12 -23.0(8) . . . . ?
C10 C11 N1 C12 159.6(5) . . . . ?
C15 C12 N1 C11 104.5(5) . . . . ?
C13 C12 N1 C11 -132.5(5) . . . . ?
C15 C12 N1 N2 -103.3(4) . . . . ?
C13 C12 N1 N2 19.7(4) . . . . ?
O2 C14 N2 N1 -172.6(4) . . . . ?
C13 C14 N2 N1 7.6(5) . . . . ?
O2 C14 N2 C9 -23.3(8) . . . . ?
C13 C14 N2 C9 157.0(5) . . . . ?
C11 N1 N2 C14 139.8(4) . . . . ?
C12 N1 N2 C14 -18.4(5) . . . . ?
C11 N1 N2 C9 -17.4(5) . . . . ?
C12 N1 N2 C9 -175.6(3) . . . . ?
C8A C9 N2 C14 119.1(10) . . . . ?
C10 C9 N2 C14 -132.0(5) . . . . ?
C8 C9 N2 C14 102.6(7) . . . . ?
C8A C9 N2 N1 -91.0(9) . . . . ?
C10 C9 N2 N1 17.9(4) . . . . ?
C8 C9 N2 N1 -107.5(6) . . . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 992847'
