# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_AZ12576722
#TrackingRef '11302_web_deposit_cif_file_0_AnneErtan_1337089988.AZ12576722.cif'

#==============================================================================
_audit_creation_method           'maXus and PLATON'
_chemical_name_systematic        
;
(4R)-4-(4-bromophenyl)-1-(4-methoxyphenyl)-3,3-dimethylazetidin-2-one
;
_chemical_name_common            
; AZ12576722, AZ SBBG: 2006-10-306
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N O2'

_chemical_formula_structural     ?
_chemical_formula_sum            'C18 H18 Br N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         360.23

_chemical_compound_source        
;Laboratory at AlderleyPark Ba 001 isomer 2, crystallised from diethyl
ether by evaporation
;
_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_cell_measurement_temperature    200
_refine_ls_hydrogen_treatment    refU
_diffrn_measurement_device       KappaCCD
_computing_data_collection       'KappaCCD Software (Nonius, 2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEPII (Johnson, 1976), PLATON (Spek, 2003)
;
_computing_publication_material  'PLATON (Spek, 2003)'

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  all


_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.01461
_diffrn_orient_matrix_UB_12      -0.08277
_diffrn_orient_matrix_UB_13      0.00996
_diffrn_orient_matrix_UB_21      -0.13305
_diffrn_orient_matrix_UB_22      0.00648
_diffrn_orient_matrix_UB_23      0.02531
_diffrn_orient_matrix_UB_31      -0.10047
_diffrn_orient_matrix_UB_32      -0.02061
_diffrn_orient_matrix_UB_33      -0.03206

_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_special_details           
;
?
;
_diffrn_radiation_type           ' MoK\a'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   5.9750(2)
_cell_length_b                   11.6900(3)
_cell_length_c                   23.7850(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1661.33(8)
_diffrn_reflns_number            3815
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_full        27.48
_cell_measurement_reflns_used    19607
_cell_measurement_theta_min      1.018
_cell_measurement_theta_max      27.485
_diffrn_measurement_method       CCD
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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'
O O 0.0106 0.0060 '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'

_exptl_absorpt_coefficient_mu    2.481
_reflns_number_total             3788
_reflns_number_gt                2938
_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3788
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.056
#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS/PLATON 2003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Br22 Br Uani 1.41145(7) -0.35959(3) 0.06174(1) 1.000 0.0615(1) . .
O5 O Uani 0.5604(3) 0.12138(19) 0.25147(8) 1.000 0.0470(7) . .
O20 O Uani 0.7497(4) 0.4325(2) 0.01772(9) 1.000 0.0595(8) . .
N1 N Uani 0.8537(4) 0.1060(2) 0.18601(10) 1.000 0.0371(7) . .
C2 C Uani 0.7408(5) 0.0881(2) 0.23559(12) 1.000 0.0380(9) . .
C3 C Uani 0.9320(5) 0.0153(2) 0.26021(11) 1.000 0.0368(8) . .
C4 C Uani 1.0566(5) 0.0439(2) 0.20365(11) 1.000 0.0356(8) . .
C6 C Uani 1.0357(5) 0.0682(3) 0.31169(12) 1.000 0.0491(10) . .
C7 C Uani 0.8692(5) -0.1096(2) 0.26953(13) 1.000 0.0480(10) . .
C8 C Uani 1.1310(4) -0.0542(2) 0.16705(11) 1.000 0.0348(8) . .
C9 C Uani 1.3353(5) -0.1055(3) 0.17979(13) 1.000 0.0429(9) . .
C10 C Uani 1.4162(6) -0.1966(2) 0.14891(12) 1.000 0.0456(9) . .
C11 C Uani 1.2910(5) -0.2364(2) 0.10443(11) 1.000 0.0415(9) . .
C12 C Uani 1.0862(6) -0.1899(3) 0.09130(11) 1.000 0.0450(9) . .
C13 C Uani 1.0070(5) -0.0972(3) 0.12252(12) 1.000 0.0407(9) . .
C14 C Uani 0.8275(5) 0.1867(2) 0.14176(11) 1.000 0.0362(8) . .
C15 C Uani 0.9962(5) 0.2020(3) 0.10335(12) 1.000 0.0453(10) . .
C16 C Uani 0.9760(5) 0.2839(2) 0.06118(12) 1.000 0.0447(9) . .
C17 C Uani 0.7846(5) 0.3496(2) 0.05753(12) 1.000 0.0445(9) . .
C18 C Uani 0.6144(6) 0.3325(3) 0.09598(14) 1.000 0.0521(11) . .
C19 C Uani 0.6314(5) 0.2512(3) 0.13789(13) 1.000 0.0439(10) . .
C21 C Uani 0.9297(7) 0.4602(3) -0.01826(15) 1.000 0.0673(14) . .
H4 H Uiso 1.19086 0.08597 0.21174 1.000 0.0350 . .
H6A H Uiso 1.15214 0.01878 0.32518 1.000 0.0566 . .
H6B H Uiso 1.09804 0.14138 0.30218 1.000 0.0566 . .
H6C H Uiso 0.92434 0.07768 0.34038 1.000 0.0566 . .
H7A H Uiso 0.99505 -0.15027 0.28467 1.000 0.0612 . .
H7B H Uiso 0.74635 -0.11357 0.29547 1.000 0.0612 . .
H7C H Uiso 0.82595 -0.14347 0.23437 1.000 0.0612 . .
H9 H Uiso 1.42299 -0.07763 0.21074 1.000 0.0476 . .
H10 H Uiso 1.55643 -0.23058 0.15925 1.000 0.0533 . .
H12 H Uiso 1.00140 -0.22091 0.06065 1.000 0.0698 . .
H13 H Uiso 0.86476 -0.06367 0.11365 1.000 0.0502 . .
H15 H Uiso 1.12893 0.15579 0.10513 1.000 0.0543 . .
H16 H Uiso 1.09695 0.29466 0.03518 1.000 0.0645 . .
H18 H Uiso 0.48021 0.37746 0.09378 1.000 0.0585 . .
H19 H Uiso 0.51347 0.23729 0.16442 1.000 0.0445 . .
H21A H Uiso 0.88504 0.51967 -0.04375 1.000 0.1030 . .
H21B H Uiso 1.05594 0.48547 0.00335 1.000 0.1030 . .
H21C H Uiso 0.96984 0.39307 -0.03925 1.000 0.1030 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br22 0.0881(3) 0.0435(2) 0.0529(2) -0.0081(1) 0.0195(2) 0.0078(2)
O5 0.0315(11) 0.0555(13) 0.0540(11) -0.0058(9) 0.0084(11) 0.0026(11)
O20 0.0747(16) 0.0481(13) 0.0557(13) 0.0110(11) -0.0077(13) 0.0151(13)
N1 0.0316(12) 0.0393(12) 0.0404(12) 0.0011(10) 0.0006(10) 0.0058(10)
C2 0.0359(16) 0.0352(15) 0.0428(15) -0.0057(12) -0.0019(13) -0.0037(13)
C3 0.0333(15) 0.0388(15) 0.0384(14) -0.0023(11) 0.0021(13) 0.0020(13)
C4 0.0292(14) 0.0354(14) 0.0422(14) -0.0012(11) -0.0027(12) 0.0028(12)
C6 0.0472(19) 0.061(2) 0.0392(15) -0.0055(14) 0.0001(14) 0.0064(15)
C7 0.0510(19) 0.0418(16) 0.0512(16) 0.0089(13) 0.0063(14) 0.0013(14)
C8 0.0388(16) 0.0329(13) 0.0326(13) 0.0011(10) 0.0020(12) 0.0011(12)
C9 0.0397(16) 0.0419(16) 0.0471(15) -0.0084(13) -0.0049(13) 0.0040(12)
C10 0.0444(16) 0.0359(15) 0.0564(17) -0.0003(13) 0.0052(16) 0.0036(15)
C11 0.0549(19) 0.0343(15) 0.0353(14) 0.0000(11) 0.0102(14) 0.0036(13)
C12 0.0582(18) 0.0432(15) 0.0336(13) -0.0013(12) -0.0013(15) -0.0048(16)
C13 0.0419(16) 0.0409(16) 0.0394(14) 0.0041(12) -0.0046(12) 0.0031(13)
C14 0.0374(15) 0.0331(13) 0.0381(14) -0.0026(11) -0.0059(12) 0.0034(12)
C15 0.0452(17) 0.0441(17) 0.0466(16) 0.0027(13) 0.0012(14) 0.0135(14)
C16 0.0538(18) 0.0412(15) 0.0392(14) 0.0002(13) -0.0022(14) 0.0069(13)
C17 0.0548(18) 0.0358(15) 0.0428(15) 0.0012(14) -0.0091(14) 0.0035(14)
C18 0.0487(19) 0.0455(18) 0.0621(19) -0.0008(14) -0.0094(16) 0.0183(15)
C19 0.0371(17) 0.0416(16) 0.0530(17) -0.0021(12) -0.0014(13) 0.0075(13)
C21 0.086(3) 0.052(2) 0.064(2) 0.0182(17) -0.014(2) 0.000(2)

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

# MOLECULAR GEOMETRY/PLATON 2003

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All esds are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br22 C11 1.903(3) . . yes
O5 C2 1.207(3) . . yes
O20 C17 1.371(3) . . yes
O20 C21 1.412(5) . . yes
N1 C2 1.375(4) . . yes
N1 C4 1.474(4) . . yes
N1 C14 1.422(3) . . yes
C2 C3 1.540(4) . . no
C3 C4 1.573(4) . . no
C3 C6 1.505(4) . . no
C3 C7 1.524(3) . . no
C4 C8 1.507(3) . . no
C8 C9 1.393(4) . . no
C8 C13 1.387(4) . . no
C9 C10 1.381(4) . . no
C10 C11 1.377(4) . . no
C11 C12 1.375(5) . . no
C12 C13 1.396(5) . . no
C14 C15 1.372(4) . . no
C14 C19 1.396(4) . . no
C15 C16 1.392(4) . . no
C16 C17 1.380(4) . . no
C17 C18 1.382(5) . . no
C18 C19 1.381(5) . . no
C4 H4 0.9604 . . no
C6 H6A 0.9596 . . no
C6 H6B 0.9601 . . no
C6 H6C 0.9595 . . no
C7 H7A 0.9598 . . no
C7 H7B 0.9600 . . no
C7 H7C 0.9607 . . no
C9 H9 0.9605 . . no
C10 H10 0.9593 . . no
C12 H12 0.9590 . . no
C13 H13 0.9594 . . no
C15 H15 0.9605 . . no
C16 H16 0.9594 . . no
C18 H18 0.9601 . . no
C19 H19 0.9598 . . no
C21 H21A 0.9603 . . no
C21 H21B 0.9594 . . no
C21 H21C 0.9605 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O20 C21 117.7(3) . . . yes
C2 N1 C4 94.8(2) . . . yes
C2 N1 C14 133.0(2) . . . yes
C4 N1 C14 128.9(2) . . . yes
O5 C2 N1 131.1(3) . . . yes
O5 C2 C3 136.2(3) . . . yes
N1 C2 C3 92.7(2) . . . yes
C2 C3 C4 84.75(19) . . . no
C2 C3 C6 112.8(2) . . . no
C2 C3 C7 113.7(2) . . . no
C4 C3 C6 114.4(2) . . . no
C4 C3 C7 116.4(2) . . . no
C6 C3 C7 112.1(2) . . . no
N1 C4 C3 87.6(2) . . . yes
N1 C4 C8 116.9(2) . . . yes
C3 C4 C8 118.2(2) . . . no
C4 C8 C9 117.4(2) . . . no
C4 C8 C13 124.0(2) . . . no
C9 C8 C13 118.6(3) . . . no
C8 C9 C10 121.5(3) . . . no
C9 C10 C11 118.6(3) . . . no
Br22 C11 C10 117.4(2) . . . yes
Br22 C11 C12 121.0(2) . . . yes
C10 C11 C12 121.6(3) . . . no
C11 C12 C13 119.2(3) . . . no
C8 C13 C12 120.4(3) . . . no
N1 C14 C15 119.9(3) . . . yes
N1 C14 C19 120.0(3) . . . yes
C15 C14 C19 120.1(3) . . . no
C14 C15 C16 120.4(3) . . . no
C15 C16 C17 120.0(3) . . . no
O20 C17 C16 124.3(3) . . . yes
O20 C17 C18 116.6(3) . . . yes
C16 C17 C18 119.2(3) . . . no
C17 C18 C19 121.5(3) . . . no
C14 C19 C18 118.7(3) . . . no
N1 C4 H4 119.46 . . . no
C3 C4 H4 109.43 . . . no
C8 C4 H4 105.01 . . . no
C3 C6 H6A 108.85 . . . no
C3 C6 H6B 109.52 . . . no
C3 C6 H6C 109.91 . . . no
H6A C6 H6B 109.51 . . . no
H6A C6 H6C 109.54 . . . no
H6B C6 H6C 109.49 . . . no
C3 C7 H7A 109.65 . . . no
C3 C7 H7B 109.15 . . . no
C3 C7 H7C 109.54 . . . no
H7A C7 H7B 109.51 . . . no
H7A C7 H7C 109.46 . . . no
H7B C7 H7C 109.50 . . . no
C8 C9 H9 119.91 . . . no
C10 C9 H9 118.57 . . . no
C9 C10 H10 119.25 . . . no
C11 C10 H10 122.12 . . . no
C11 C12 H12 119.57 . . . no
C13 C12 H12 121.24 . . . no
C8 C13 H13 119.54 . . . no
C12 C13 H13 120.02 . . . no
C14 C15 H15 120.26 . . . no
C16 C15 H15 119.36 . . . no
C15 C16 H16 119.30 . . . no
C17 C16 H16 120.70 . . . no
C17 C18 H18 119.95 . . . no
C19 C18 H18 118.52 . . . no
C14 C19 H19 118.77 . . . no
C18 C19 H19 122.49 . . . no
O20 C21 H21A 109.70 . . . no
O20 C21 H21B 110.17 . . . no
O20 C21 H21C 108.53 . . . no
H21A C21 H21B 109.50 . . . no
H21A C21 H21C 109.43 . . . no
H21B C21 H21C 109.49 . . . no

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
C21 O20 C17 C16 -6.6(4) . . . . no
C21 O20 C17 C18 173.4(3) . . . . no
C4 N1 C2 O5 176.3(3) . . . . no
C4 N1 C2 C3 -2.7(2) . . . . no
C2 N1 C4 C8 123.2(2) . . . . no
C14 N1 C4 C3 164.0(3) . . . . no
C14 N1 C4 C8 -75.4(3) . . . . no
C2 N1 C14 C15 164.7(3) . . . . no
C2 N1 C14 C19 -14.5(4) . . . . no
C4 N1 C14 C15 10.5(4) . . . . no
C4 N1 C14 C19 -168.7(3) . . . . no
C2 N1 C4 C3 2.6(2) . . . . no
C14 N1 C2 O5 16.1(5) . . . . no
C14 N1 C2 C3 -162.8(3) . . . . no
N1 C2 C3 C6 116.8(2) . . . . no
N1 C2 C3 C4 2.50(19) . . . . no
O5 C2 C3 C4 -176.4(3) . . . . no
O5 C2 C3 C6 -62.0(4) . . . . no
O5 C2 C3 C7 67.1(4) . . . . no
N1 C2 C3 C7 -114.1(2) . . . . no
C7 C3 C4 N1 111.6(2) . . . . no
C2 C3 C4 N1 -2.33(18) . . . . no
C2 C3 C4 C8 -121.8(2) . . . . no
C7 C3 C4 C8 -7.9(4) . . . . no
C6 C3 C4 C8 125.5(3) . . . . no
C6 C3 C4 N1 -115.0(2) . . . . no
N1 C4 C8 C13 -8.0(4) . . . . no
N1 C4 C8 C9 173.2(2) . . . . no
C3 C4 C8 C13 94.6(3) . . . . no
C3 C4 C8 C9 -84.1(3) . . . . no
C4 C8 C9 C10 179.4(3) . . . . no
C9 C8 C13 C12 0.0(4) . . . . no
C13 C8 C9 C10 0.6(4) . . . . no
C4 C8 C13 C12 -178.8(3) . . . . no
C8 C9 C10 C11 0.4(4) . . . . no
C9 C10 C11 Br22 178.5(2) . . . . no
C9 C10 C11 C12 -1.9(4) . . . . no
Br22 C11 C12 C13 -177.9(2) . . . . no
C10 C11 C12 C13 2.5(4) . . . . no
C11 C12 C13 C8 -1.5(5) . . . . no
C19 C14 C15 C16 1.7(4) . . . . no
N1 C14 C19 C18 177.2(3) . . . . no
N1 C14 C15 C16 -177.5(3) . . . . no
C15 C14 C19 C18 -2.0(5) . . . . no
C14 C15 C16 C17 -0.6(4) . . . . no
C15 C16 C17 O20 179.7(3) . . . . no
C15 C16 C17 C18 -0.3(4) . . . . no
C16 C17 C18 C19 -0.1(5) . . . . no
O20 C17 C18 C19 180.0(3) . . . . no
C17 C18 C19 C14 1.2(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br22 O20 3.330(2) . 1_645 no
Br22 H18 3.1935 . 1_645 no
Br22 H21B 3.1179 . 1_545 no
Br22 H12 3.1062 . 3_545 no
Br22 H6C 3.1596 . 4_745 no
O5 C4 3.343(3) . 1_455 no
O5 C19 3.127(4) . . no
O5 C10 3.188(3) . 4_755 no
O20 Br22 3.330(2) . 1_465 no
O5 H9 2.6504 . 1_455 no
O5 H4 2.4371 . 1_455 no
O5 H10 2.8269 . 4_755 no
O5 H19 2.4903 . . no
N1 H13 2.6269 . . no
C2 C9 3.571(4) . 1_455 no
C4 O5 3.343(3) . 1_655 no
C7 C9 3.509(4) . . no
C7 C13 3.595(4) . . no
C8 C15 3.452(4) . . no
C9 C2 3.571(4) . 1_655 no
C9 C7 3.509(4) . . no
C10 O5 3.188(3) . 4_745 no
C13 C7 3.595(4) . . no
C13 C15 3.528(5) . . no
C13 C14 3.518(4) . . no
C14 C13 3.518(4) . . no
C15 C8 3.452(4) . . no
C15 C13 3.528(5) . . no
C19 O5 3.127(4) . . no
C2 H19 2.7843 . . no
C2 H9 2.7765 . 1_455 no
C4 H15 2.7182 . . no
C7 H9 3.0337 . 1_455 no
C8 H15 2.8627 . . no
C8 H7C 2.6410 . . no
C11 H6C 2.8465 . 4_745 no
C11 H21A 2.9695 . 3_555 no
C12 H21A 2.9030 . 3_555 no
C13 H15 3.0738 . . no
C13 H7C 2.9224 . . no
C13 H21A 3.0714 . 3_555 no
C14 H13 3.0105 . . no
C14 H7A 2.7961 . 4_755 no
C16 H21B 2.7699 . . no
C16 H21C 2.7085 . . no
C17 H16 2.9939 . 3_455 no
C18 H21C 3.0855 . 3_455 no
C19 H21C 3.0464 . 3_455 no
C21 H16 2.5217 . . no
C21 H15 3.0557 . 3_455 no
H4 O5 2.4371 . 1_655 no
H4 H6B 2.3140 . . no
H4 H9 2.3626 . . no
H6A H7A 2.3905 . . no
H6B H4 2.3140 . . no
H6C Br22 3.1596 . 4_755 no
H6C C11 2.8465 . 4_755 no
H7A H6A 2.3905 . . no
H7A C14 2.7961 . 4_745 no
H7B H19 2.5219 . 4_645 no
H7C C8 2.6410 . . no
H7C C13 2.9224 . . no
H7C H9 2.5894 . 1_455 no
H9 O5 2.6504 . 1_655 no
H9 C2 2.7765 . 1_655 no
H9 C7 3.0337 . 1_655 no
H9 H4 2.3626 . . no
H9 H7C 2.5894 . 1_655 no
H10 O5 2.8269 . 4_745 no
H12 Br22 3.1062 . 3_445 no
H13 N1 2.6269 . . no
H13 C14 3.0105 . . no
H15 C4 2.7182 . . no
H15 C8 2.8627 . . no
H15 C13 3.0738 . . no
H15 C21 3.0557 . 3_555 no
H16 C21 2.5217 . . no
H16 H21B 2.3683 . . no
H16 H21C 2.2437 . . no
H16 C17 2.9939 . 3_555 no
H18 Br22 3.1935 . 1_465 no
H19 O5 2.4903 . . no
H19 C2 2.7843 . . no
H19 H7B 2.5219 . 4_655 no
H21A C11 2.9695 . 3_455 no
H21A C12 2.9030 . 3_455 no
H21A C13 3.0714 . 3_455 no
H21B Br22 3.1179 . 1_565 no
H21B C16 2.7699 . . no
H21B H16 2.3683 . . no
H21C C16 2.7085 . . no
H21C H16 2.2437 . . no
H21C C18 3.0855 . 3_555 no
H21C C19 3.0464 . 3_555 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C4 H4 O5 0.9600 2.4400 3.343(3) 157.00 1_655 yes
C19 H19 O5 0.9600 2.4900 3.127(4) 124.00 . yes

#===End of Crystallographic Information File


_database_code_depnum_ccdc_archive 'CCDC 882283'