# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_123
_database_code_depnum_ccdc_archive 'CCDC 1061453'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 Br2 N O3'
_chemical_formula_weight         545.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   30.6044(17)
_cell_length_b                   38.834(3)
_cell_length_c                   7.7980(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9267.9(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3126
_cell_measurement_theta_min      5.40
_cell_measurement_theta_max      64.54

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4384
_exptl_absorpt_coefficient_mu    4.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3358
_exptl_absorpt_correction_T_max  0.3892
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14487
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         5.40
_diffrn_reflns_theta_max         64.54
_reflns_number_total             3126
_reflns_number_gt                2461
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.0850P)²+29.4454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_number_reflns         3126
_refine_ls_number_parameters     282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
Br31 Br 0.42227(3) 0.38308(2) 0.5980(2) 0.1047(5) Uani 1 1 d . . .
Br22 Br 0.30428(4) 0.16806(4) 1.39688(19) 0.1252(6) Uani 1 1 d . . .
O29 O 0.28693(13) 0.28575(12) 0.8739(11) 0.088(2) Uani 1 1 d . . .
O4 O 0.40017(14) 0.24701(12) 0.7022(7) 0.0601(14) Uani 1 1 d . . .
O20 O 0.3613(2) 0.30970(14) 1.1751(10) 0.090(2) Uani 1 1 d . . .
N1 N 0.42336(16) 0.22535(17) 0.9584(10) 0.0625(17) Uani 1 1 d . . .
C21 C 0.3403(4) 0.3402(3) 1.2387(17) 0.107(4) Uani 1 1 d . . .
H21A H 0.3094 0.3386 1.2200 0.160 Uiso 1 1 calc R . .
H21B H 0.3516 0.3600 1.1795 0.160 Uiso 1 1 calc R . .
H21C H 0.3460 0.3425 1.3593 0.160 Uiso 1 1 calc R . .
C30 C 0.2446(2) 0.2976(2) 0.9190(15) 0.084(3) Uani 1 1 d . . .
H30A H 0.2471 0.3161 1.0002 0.126 Uiso 1 1 calc R . .
H30B H 0.2283 0.2791 0.9692 0.126 Uiso 1 1 calc R . .
H30C H 0.2298 0.3057 0.8182 0.126 Uiso 1 1 calc R . .
C24 C 0.31666(19) 0.30995(17) 0.8111(12) 0.059(2) Uani 1 1 d . . .
C23 C 0.35854(18) 0.29748(16) 0.7832(11) 0.0504(17) Uani 1 1 d . . .
C3 C 0.37000(19) 0.26045(15) 0.8247(12) 0.0568(19) Uani 1 1 d . . .
H3 H 0.3433 0.2465 0.8230 0.068 Uiso 1 1 calc R . .
C5 C 0.4136(2) 0.21588(16) 0.7783(14) 0.064(2) Uani 1 1 d . . .
H5 H 0.3885 0.2002 0.7790 0.076 Uiso 1 1 calc R . .
C6 C 0.4504(2) 0.19839(18) 0.6812(13) 0.066(2) Uani 1 1 d . . .
C7 C 0.4407(3) 0.1896(2) 0.5174(15) 0.088(3) Uani 1 1 d . . .
H7 H 0.4142 0.1955 0.4671 0.105 Uiso 1 1 calc R . .
C8 C 0.4736(4) 0.1708(3) 0.4259(19) 0.113(4) Uani 1 1 d . . .
H8 H 0.4687 0.1632 0.3145 0.136 Uiso 1 1 calc R . .
C9 C 0.5131(4) 0.1643(3) 0.508(2) 0.118(5) Uani 1 1 d . . .
H9 H 0.5344 0.1524 0.4477 0.142 Uiso 1 1 calc R . .
C11 C 0.4887(2) 0.1917(2) 0.7609(15) 0.077(3) Uani 1 1 d . . .
C10 C 0.5225(4) 0.1740(3) 0.668(2) 0.100(4) Uani 1 1 d . . .
H10 H 0.5496 0.1694 0.7173 0.121 Uiso 1 1 calc R . .
C12 C 0.4989(3) 0.2039(3) 0.9346(18) 0.100(4) Uani 1 1 d . . .
H12A H 0.5291 0.2115 0.9393 0.120 Uiso 1 1 calc R . .
H12B H 0.4953 0.1852 1.0158 0.120 Uiso 1 1 calc R . .
C13 C 0.4690(2) 0.2336(2) 0.9830(15) 0.085(3) Uani 1 1 d . . .
H13A H 0.4738 0.2396 1.1022 0.102 Uiso 1 1 calc R . .
H13B H 0.4763 0.2536 0.9138 0.102 Uiso 1 1 calc R . .
C2 C 0.3935(2) 0.25523(18) 0.9969(11) 0.059(2) Uani 1 1 d . . .
H2 H 0.4115 0.2756 1.0195 0.071 Uiso 1 1 calc R . .
C28 C 0.3897(2) 0.31957(17) 0.7254(12) 0.062(2) Uani 1 1 d . . .
H28 H 0.4180 0.3117 0.7070 0.074 Uiso 1 1 calc R . .
C27 C 0.3796(2) 0.35359(18) 0.6939(12) 0.064(2) Uani 1 1 d . . .
C26 C 0.3369(3) 0.36571(19) 0.7156(13) 0.068(2) Uani 1 1 d . . .
H26 H 0.3298 0.3883 0.6871 0.081 Uiso 1 1 calc R . .
C25 C 0.3061(2) 0.3439(2) 0.7792(14) 0.075(3) Uani 1 1 d . . .
H25 H 0.2780 0.3518 0.8010 0.090 Uiso 1 1 calc R . .
C14 C 0.3647(2) 0.24951(19) 1.1471(12) 0.0606(19) Uani 1 1 d . . .
C15 C 0.3514(2) 0.2171(2) 1.2032(12) 0.068(2) Uani 1 1 d . . .
H15 H 0.3629 0.1974 1.1516 0.081 Uiso 1 1 calc R . .
C16 C 0.3226(3) 0.2139(2) 1.3298(15) 0.081(3) Uani 1 1 d . . .
C17 C 0.3063(3) 0.2414(4) 1.4175(15) 0.100(3) Uani 1 1 d . . .
H17 H 0.2867 0.2382 1.5075 0.120 Uiso 1 1 calc R . .
C18 C 0.3191(3) 0.2742(3) 1.3705(16) 0.085(3) Uani 1 1 d . . .
H18 H 0.3088 0.2933 1.4300 0.102 Uiso 1 1 calc R . .
C19 C 0.3469(2) 0.2782(2) 1.2368(13) 0.069(2) Uani 1 1 d . . .


_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
Br31 C27 1.891(7) . ?
Br22 C16 1.937(9) . ?
O29 C24 1.397(8) . ?
O29 C30 1.419(8) . ?
O4 C5 1.408(8) . ?
O4 C3 1.428(9) . ?
O20 C19 1.388(10) . ?
O20 C21 1.436(11) . ?
N1 C13 1.445(9) . ?
N1 C5 1.483(12) . ?
N1 C2 1.508(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C24 C25 1.379(10) . ?
C24 C23 1.387(8) . ?
C23 C28 1.359(9) . ?
C23 C3 1.515(8) . ?
C3 C2 1.536(12) . ?
C3 H3 0.9800 . ?
C5 C6 1.518(11) . ?
C5 H5 0.9800 . ?
C6 C11 1.351(12) . ?
C6 C7 1.355(14) . ?
C7 C8 1.435(14) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.333(19) . ?
C9 H9 0.9300 . ?
C11 C10 1.440(13) . ?
C11 C12 1.468(15) . ?
C10 H10 0.9300 . ?
C12 C13 1.521(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C2 C14 1.482(11) . ?
C2 H2 0.9800 . ?
C28 C27 1.379(9) . ?
C28 H28 0.9300 . ?
C27 C26 1.399(10) . ?
C26 C25 1.363(11) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C14 C15 1.394(10) . ?
C14 C19 1.423(11) . ?
C15 C16 1.330(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(15) . ?
C17 C18 1.383(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(14) . ?
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
C24 O29 C30 117.6(5) . . ?
C5 O4 C3 102.7(6) . . ?
C19 O20 C21 117.8(8) . . ?
C13 N1 C5 112.1(7) . . ?
C13 N1 C2 112.9(6) . . ?
C5 N1 C2 104.9(6) . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O29 C30 H30A 109.5 . . ?
O29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C25 C24 C23 121.5(6) . . ?
C25 C24 O29 123.6(6) . . ?
C23 C24 O29 114.9(6) . . ?
C28 C23 C24 118.6(6) . . ?
C28 C23 C3 120.5(5) . . ?
C24 C23 C3 120.8(6) . . ?
O4 C3 C23 110.7(6) . . ?
O4 C3 C2 103.6(5) . . ?
C23 C3 C2 114.8(6) . . ?
O4 C3 H3 109.2 . . ?
C23 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
O4 C5 N1 104.2(6) . . ?
O4 C5 C6 113.0(7) . . ?
N1 C5 C6 115.7(6) . . ?
O4 C5 H5 107.9 . . ?
N1 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C11 C6 C7 125.2(9) . . ?
C11 C6 C5 120.0(9) . . ?
C7 C6 C5 114.8(8) . . ?
C6 C7 C8 116.3(10) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 H7 121.8 . . ?
C9 C8 C7 118.1(13) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C10 C9 C8 124.8(12) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C6 C11 C10 119.0(11) . . ?
C6 C11 C12 123.3(8) . . ?
C10 C11 C12 117.6(10) . . ?
C9 C10 C11 116.6(13) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 H10 121.7 . . ?
C11 C12 C13 110.1(8) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
N1 C13 C12 112.4(8) . . ?
N1 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C2 N1 113.7(6) . . ?
C14 C2 C3 115.7(5) . . ?
N1 C2 C3 102.2(6) . . ?
C14 C2 H2 108.3 . . ?
N1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C23 C28 C27 120.5(6) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C27 C26 120.6(7) . . ?
C28 C27 Br31 119.8(5) . . ?
C26 C27 Br31 119.2(6) . . ?
C25 C26 C27 118.8(7) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C26 C25 C24 119.8(6) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C15 C14 C19 116.2(8) . . ?
C15 C14 C2 123.8(7) . . ?
C19 C14 C2 119.9(7) . . ?
C16 C15 C14 120.7(8) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 122.8(9) . . ?
C15 C16 Br22 118.5(8) . . ?
C17 C16 Br22 118.6(9) . . ?
C16 C17 C18 119.0(10) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 119.1(10) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 O20 124.5(9) . . ?
C18 C19 C14 122.1(9) . . ?
O20 C19 C14 113.4(8) . . ?

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
C30 O29 C24 C25 -4.9(14) . . . . ?
C30 O29 C24 C23 174.7(9) . . . . ?
C25 C24 C23 C28 0.9(13) . . . . ?
O29 C24 C23 C28 -178.7(9) . . . . ?
C25 C24 C23 C3 177.9(8) . . . . ?
O29 C24 C23 C3 -1.7(12) . . . . ?
C5 O4 C3 C23 168.7(6) . . . . ?
C5 O4 C3 C2 45.1(6) . . . . ?
C28 C23 C3 O4 -39.2(10) . . . . ?
C24 C23 C3 O4 143.9(7) . . . . ?
C28 C23 C3 C2 77.6(10) . . . . ?
C24 C23 C3 C2 -99.3(8) . . . . ?
C3 O4 C5 N1 -46.7(6) . . . . ?
C3 O4 C5 C6 -173.1(6) . . . . ?
C13 N1 C5 O4 -93.4(7) . . . . ?
C2 N1 C5 O4 29.4(6) . . . . ?
C13 N1 C5 C6 31.2(8) . . . . ?
C2 N1 C5 C6 154.0(6) . . . . ?
O4 C5 C6 C11 121.4(8) . . . . ?
N1 C5 C6 C11 1.4(10) . . . . ?
O4 C5 C6 C7 -60.7(9) . . . . ?
N1 C5 C6 C7 179.4(7) . . . . ?
C11 C6 C7 C8 2.2(14) . . . . ?
C5 C6 C7 C8 -175.6(8) . . . . ?
C6 C7 C8 C9 -2.6(15) . . . . ?
C7 C8 C9 C10 1.0(19) . . . . ?
C7 C6 C11 C10 -0.0(14) . . . . ?
C5 C6 C11 C10 177.7(7) . . . . ?
C7 C6 C11 C12 175.4(9) . . . . ?
C5 C6 C11 C12 -6.9(13) . . . . ?
C8 C9 C10 C11 1.2(18) . . . . ?
C6 C11 C10 C9 -1.7(15) . . . . ?
C12 C11 C10 C9 -177.4(11) . . . . ?
C6 C11 C12 C13 -19.1(13) . . . . ?
C10 C11 C12 C13 156.4(9) . . . . ?
C5 N1 C13 C12 -58.8(10) . . . . ?
C2 N1 C13 C12 -176.9(9) . . . . ?
C11 C12 C13 N1 52.3(12) . . . . ?
C13 N1 C2 C14 -114.2(8) . . . . ?
C5 N1 C2 C14 123.5(7) . . . . ?
C13 N1 C2 C3 120.4(7) . . . . ?
C5 N1 C2 C3 -1.9(6) . . . . ?
O4 C3 C2 C14 -149.7(6) . . . . ?
C23 C3 C2 C14 89.4(7) . . . . ?
O4 C3 C2 N1 -25.6(6) . . . . ?
C23 C3 C2 N1 -146.5(5) . . . . ?
C24 C23 C28 C27 -0.5(13) . . . . ?
C3 C23 C28 C27 -177.5(8) . . . . ?
C23 C28 C27 C26 -2.1(14) . . . . ?
C23 C28 C27 Br31 -175.5(7) . . . . ?
C28 C27 C26 C25 4.3(15) . . . . ?
Br31 C27 C26 C25 177.7(8) . . . . ?
C27 C26 C25 C24 -3.9(15) . . . . ?
C23 C24 C25 C26 1.4(15) . . . . ?
O29 C24 C25 C26 -179.1(10) . . . . ?
N1 C2 C14 C15 -26.6(10) . . . . ?
C3 C2 C14 C15 91.3(8) . . . . ?
N1 C2 C14 C19 157.2(7) . . . . ?
C3 C2 C14 C19 -84.9(9) . . . . ?
C19 C14 C15 C16 2.2(11) . . . . ?
C2 C14 C15 C16 -174.2(8) . . . . ?
C14 C15 C16 C17 -3.6(14) . . . . ?
C14 C15 C16 Br22 178.2(6) . . . . ?
C15 C16 C17 C18 1.8(15) . . . . ?
Br22 C16 C17 C18 -179.9(7) . . . . ?
C16 C17 C18 C19 1.3(14) . . . . ?
C17 C18 C19 O20 178.5(8) . . . . ?
C17 C18 C19 C14 -2.6(13) . . . . ?
C21 O20 C19 C18 -10.3(13) . . . . ?
C21 O20 C19 C14 170.7(8) . . . . ?
C15 C14 C19 C18 0.9(11) . . . . ?
C2 C14 C19 C18 177.4(8) . . . . ?
C15 C14 C19 O20 180.0(7) . . . . ?
C2 C14 C19 O20 -3.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        64.54
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.081
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pi3
_database_code_depnum_ccdc_archive 'CCDC 1061457'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cl N2'
_chemical_formula_weight         356.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna21

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

_cell_length_a                   19.212(3)
_cell_length_b                   16.673(2)
_cell_length_c                   5.6278(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1802.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2545
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      64.85

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6450
_exptl_absorpt_correction_T_max  0.6661
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9274
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         64.85
_reflns_number_total             2545
_reflns_number_gt                2233
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.0454P)²+0.1846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_number_reflns         2545
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl26 Cl 0.52293(4) 0.75171(4) 0.9928(3) 0.0874(3) Uani 1 1 d . . .
N1 N 0.28691(10) 0.44807(12) 0.7025(4) 0.0457(5) Uani 1 1 d . . .
N10 N 0.20121(10) 0.41742(11) 0.4280(4) 0.0458(5) Uani 1 1 d . . .
C17 C 0.15100(11) 0.49655(15) 0.1374(5) 0.0463(6) Uani 1 1 d . . .
C9 C 0.24088(12) 0.39712(14) 0.6120(5) 0.0439(6) Uani 1 1 d . . .
C12 C 0.12001(12) 0.42212(15) 0.1256(5) 0.0458(6) Uani 1 1 d . . .
C3 C 0.28760(12) 0.32881(14) 0.9252(5) 0.0472(6) Uani 1 1 d . . .
C2 C 0.31749(11) 0.41013(15) 0.8969(5) 0.0459(6) Uani 1 1 d . . .
C8 C 0.23922(12) 0.31988(14) 0.7420(5) 0.0435(6) Uani 1 1 d . . .
C20 C 0.40017(11) 0.52001(15) 1.0300(5) 0.0453(6) Uani 1 1 d . . .
C11 C 0.14770(12) 0.36779(14) 0.3154(5) 0.0476(6) Uani 1 1 d . . .
H11A H 0.1116 0.3531 0.4277 0.057 Uiso 1 1 calc R . .
H11B H 0.1676 0.3194 0.2477 0.057 Uiso 1 1 calc R . .
C18 C 0.20424(12) 0.49880(14) 0.3300(5) 0.0480(6) Uani 1 1 d . . .
H18A H 0.2501 0.5106 0.2668 0.058 Uiso 1 1 calc R . .
H18B H 0.1925 0.5385 0.4495 0.058 Uiso 1 1 calc R . .
C19 C 0.36576(12) 0.44208(14) 1.0443(5) 0.0475(6) Uani 1 1 d . . .
H19 H 0.3788 0.4100 1.1720 0.057 Uiso 1 1 calc R . .
C23 C 0.47531(13) 0.66279(15) 1.0094(7) 0.0584(8) Uani 1 1 d . . .
C24 C 0.42930(14) 0.64448(16) 0.8288(6) 0.0609(8) Uani 1 1 d . . .
H24 H 0.4236 0.6793 0.7013 0.073 Uiso 1 1 calc R . .
C21 C 0.44681(13) 0.54192(16) 1.2100(6) 0.0555(7) Uani 1 1 d . . .
H21 H 0.4530 0.5079 1.3392 0.067 Uiso 1 1 calc R . .
C16 C 0.13253(14) 0.55676(18) -0.0209(6) 0.0597(8) Uani 1 1 d . . .
H16 H 0.1529 0.6073 -0.0114 0.072 Uiso 1 1 calc R . .
C4 C 0.29855(15) 0.26790(17) 1.0890(6) 0.0586(8) Uani 1 1 d . . .
H4 H 0.3311 0.2738 1.2101 0.070 Uiso 1 1 calc R . .
C7 C 0.20099(15) 0.24922(14) 0.7221(6) 0.0531(7) Uani 1 1 d . . .
H7 H 0.1687 0.2427 0.6006 0.064 Uiso 1 1 calc R . .
C25 C 0.39161(13) 0.57333(15) 0.8398(6) 0.0525(7) Uani 1 1 d . . .
H25 H 0.3603 0.5610 0.7193 0.063 Uiso 1 1 calc R . .
C15 C 0.08322(16) 0.5400(2) -0.1931(6) 0.0703(9) Uani 1 1 d . . .
H15 H 0.0706 0.5796 -0.3012 0.084 Uiso 1 1 calc R . .
C6 C 0.21200(15) 0.18909(16) 0.8861(6) 0.0603(8) Uani 1 1 d . . .
H6 H 0.1868 0.1416 0.8744 0.072 Uiso 1 1 calc R . .
C22 C 0.48385(14) 0.61268(18) 1.2003(7) 0.0625(8) Uani 1 1 d . . .
H22 H 0.5143 0.6263 1.3222 0.075 Uiso 1 1 calc R . .
C13 C 0.07027(13) 0.40545(18) -0.0476(5) 0.0582(7) Uani 1 1 d . . .
H13 H 0.0494 0.3552 -0.0561 0.070 Uiso 1 1 calc R . .
C14 C 0.05262(16) 0.4652(2) -0.2061(6) 0.0696(9) Uani 1 1 d . . .
H14 H 0.0197 0.4550 -0.3233 0.083 Uiso 1 1 calc R . .
C5 C 0.25999(15) 0.19829(16) 1.0681(7) 0.0632(8) Uani 1 1 d . . .
H5 H 0.2663 0.1571 1.1774 0.076 Uiso 1 1 calc R . .


_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
Cl26 C23 1.745(3) . ?
N1 C9 1.328(3) . ?
N1 C2 1.394(4) . ?
N10 C9 1.329(3) . ?
N10 C11 1.464(3) . ?
N10 C18 1.466(3) . ?
C17 C12 1.378(4) . ?
C17 C16 1.388(4) . ?
C17 C18 1.491(4) . ?
C9 C8 1.481(4) . ?
C12 C13 1.393(4) . ?
C12 C11 1.498(4) . ?
C3 C4 1.388(4) . ?
C3 C8 1.396(4) . ?
C3 C2 1.481(4) . ?
C2 C19 1.353(4) . ?
C8 C7 1.393(3) . ?
C20 C21 1.401(4) . ?
C20 C25 1.401(4) . ?
C20 C19 1.460(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19 0.9300 . ?
C23 C22 1.371(5) . ?
C23 C24 1.381(5) . ?
C24 C25 1.391(4) . ?
C24 H24 0.9300 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C16 C15 1.384(5) . ?
C16 H16 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C7 C6 1.379(4) . ?
C7 H7 0.9300 . ?
C25 H25 0.9300 . ?
C15 C14 1.381(5) . ?
C15 H15 0.9300 . ?
C6 C5 1.387(5) . ?
C6 H6 0.9300 . ?
C22 H22 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C5 H5 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
C9 N1 C2 106.9(2) . . ?
C9 N10 C11 126.6(2) . . ?
C9 N10 C18 120.4(2) . . ?
C11 N10 C18 112.8(2) . . ?
C12 C17 C16 120.7(3) . . ?
C12 C17 C18 110.7(2) . . ?
C16 C17 C18 128.6(2) . . ?
N1 C9 N10 121.2(2) . . ?
N1 C9 C8 112.4(2) . . ?
N10 C9 C8 126.4(2) . . ?
C17 C12 C13 120.6(3) . . ?
C17 C12 C11 110.9(2) . . ?
C13 C12 C11 128.4(2) . . ?
C4 C3 C8 120.9(2) . . ?
C4 C3 C2 133.0(3) . . ?
C8 C3 C2 106.0(2) . . ?
C19 C2 N1 126.2(2) . . ?
C19 C2 C3 124.1(2) . . ?
N1 C2 C3 109.7(2) . . ?
C7 C8 C3 120.0(2) . . ?
C7 C8 C9 135.0(2) . . ?
C3 C8 C9 104.9(2) . . ?
C21 C20 C25 117.5(2) . . ?
C21 C20 C19 118.8(2) . . ?
C25 C20 C19 123.6(2) . . ?
N10 C11 C12 102.49(19) . . ?
N10 C11 H11A 111.3 . . ?
C12 C11 H11A 111.3 . . ?
N10 C11 H11B 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
N10 C18 C17 102.9(2) . . ?
N10 C18 H18A 111.2 . . ?
C17 C18 H18A 111.2 . . ?
N10 C18 H18B 111.2 . . ?
C17 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C2 C19 C20 128.8(3) . . ?
C2 C19 H19 115.6 . . ?
C20 C19 H19 115.6 . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 Cl26 119.8(2) . . ?
C24 C23 Cl26 119.0(3) . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C22 C21 C20 121.7(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C24 C25 C20 120.9(3) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        64.85
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.036
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_psh1
_database_code_depnum_ccdc_archive 'CCDC 1061458'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.2900(11)
_cell_length_b                   19.234(2)
_cell_length_c                   11.2656(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.057(7)
_cell_angle_gamma                90.00
_cell_volume                     1993.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3281
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      64.81

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8629
_exptl_absorpt_correction_T_max  0.8725
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17958
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.60
_diffrn_reflns_theta_max         64.81
_reflns_number_total             3281
_reflns_number_gt                2494
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.0791P)²+0.1665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3281
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45130(13) 0.59494(6) 0.47033(11) 0.0705(4) Uani 1 1 d . . .
N14 N 0.29938(15) 0.48389(8) 0.58850(14) 0.0681(4) Uani 1 1 d . . .
H14 H 0.3723 0.4625 0.5662 0.082 Uiso 1 1 calc R . .
N4 N 0.23951(16) 0.65710(8) 0.44008(13) 0.0701(4) Uani 1 1 d . . .
C23 C 0.59539(18) 0.66459(9) 0.62336(16) 0.0608(4) Uani 1 1 d . . .
C2 C 0.48363(19) 0.66488(9) 0.51345(16) 0.0613(4) Uani 1 1 d . . .
H2 H 0.5210 0.6918 0.4505 0.074 Uiso 1 1 calc R . .
C3 C 0.33495(18) 0.69455(9) 0.53315(14) 0.0595(5) Uani 1 1 d . . .
H3 H 0.3129 0.6810 0.6125 0.071 Uiso 1 1 calc R . .
C15 C 0.24062(18) 0.54507(9) 0.54063(16) 0.0622(5) Uani 1 1 d . . .
C8 C 0.10989(19) 0.51068(10) 0.68322(17) 0.0677(5) Uani 1 1 d . . .
C17 C 0.32705(18) 0.77249(10) 0.52042(14) 0.0615(5) Uani 1 1 d . . .
C13 C 0.22242(18) 0.46243(10) 0.67814(17) 0.0651(5) Uani 1 1 d . . .
C7 C 0.12314(18) 0.56265(10) 0.59516(17) 0.0669(5) Uani 1 1 d . . .
C24 C 0.7021(2) 0.71423(11) 0.63760(18) 0.0750(5) Uani 1 1 d . . .
H24 H 0.7078 0.7463 0.5767 0.090 Uiso 1 1 calc R . .
C18 C 0.3600(2) 0.81493(10) 0.61894(18) 0.0758(6) Uani 1 1 d . . .
H18 H 0.3815 0.7952 0.6947 0.091 Uiso 1 1 calc R . .
C16 C 0.29641(19) 0.58635(10) 0.44551(17) 0.0679(5) Uani 1 1 d . . .
H16 H 0.2705 0.5635 0.3677 0.081 Uiso 1 1 calc R . .
C9 C 0.0163(2) 0.50043(13) 0.7699(2) 0.0862(7) Uani 1 1 d . . .
H9 H -0.0602 0.5309 0.7752 0.103 Uiso 1 1 calc R . .
C5 C 0.0822(2) 0.65925(12) 0.4501(2) 0.0847(6) Uani 1 1 d . . .
H5A H 0.0299 0.6347 0.3822 0.102 Uiso 1 1 calc R . .
H5B H 0.0504 0.7073 0.4447 0.102 Uiso 1 1 calc R . .
C12 C 0.2447(2) 0.40653(11) 0.7562(2) 0.0819(6) Uani 1 1 d . . .
H12 H 0.3203 0.3753 0.7521 0.098 Uiso 1 1 calc R . .
C6 C 0.0403(2) 0.62810(12) 0.5645(2) 0.0832(6) Uani 1 1 d . . .
H6A H 0.0611 0.6611 0.6297 0.100 Uiso 1 1 calc R . .
H6B H -0.0632 0.6183 0.5536 0.100 Uiso 1 1 calc R . .
C28 C 0.5904(2) 0.61695(12) 0.71412(19) 0.0860(6) Uani 1 1 d . . .
H28 H 0.5199 0.5823 0.7059 0.103 Uiso 1 1 calc R . .
C25 C 0.8019(2) 0.71752(13) 0.7414(2) 0.0868(6) Uani 1 1 d . . .
H25 H 0.8732 0.7518 0.7498 0.104 Uiso 1 1 calc R . .
C26 C 0.7954(3) 0.67074(14) 0.8303(2) 0.0913(7) Uani 1 1 d . . .
H26 H 0.8623 0.6727 0.8999 0.110 Uiso 1 1 calc R . .
C19 C 0.3615(3) 0.88640(12) 0.6070(2) 0.0946(7) Uani 1 1 d . . .
H19 H 0.3863 0.9143 0.6742 0.114 Uiso 1 1 calc R . .
C10 C 0.0398(3) 0.44474(15) 0.8466(2) 0.0966(7) Uani 1 1 d . . .
H10 H -0.0212 0.4379 0.9043 0.116 Uiso 1 1 calc R . .
C11 C 0.1519(3) 0.39895(14) 0.8392(2) 0.0933(7) Uani 1 1 d . . .
H11 H 0.1649 0.3617 0.8924 0.112 Uiso 1 1 calc R . .
C20 C 0.3266(3) 0.91628(13) 0.4962(2) 0.0986(7) Uani 1 1 d . . .
H20 H 0.3268 0.9644 0.4877 0.118 Uiso 1 1 calc R . .
C22 C 0.2918(3) 0.80389(12) 0.41054(19) 0.0950(7) Uani 1 1 d . . .
H22 H 0.2675 0.7765 0.3426 0.114 Uiso 1 1 calc R . .
C27 C 0.6900(3) 0.62064(15) 0.8175(2) 0.1024(8) Uani 1 1 d . . .
H27 H 0.6853 0.5887 0.8788 0.123 Uiso 1 1 calc R . .
C21 C 0.2918(3) 0.87486(14) 0.3994(2) 0.1132(9) Uani 1 1 d . . .
H21 H 0.2675 0.8948 0.3241 0.136 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.436(2) . ?
O1 C2 1.448(2) . ?
N14 C15 1.375(2) . ?
N14 C13 1.380(2) . ?
N14 H14 0.8600 . ?
N4 C16 1.458(2) . ?
N4 C3 1.464(2) . ?
N4 C5 1.482(3) . ?
C23 C24 1.369(3) . ?
C23 C28 1.379(3) . ?
C23 C2 1.500(2) . ?
C2 C3 1.539(2) . ?
C2 H2 0.9800 . ?
C3 C17 1.507(3) . ?
C3 H3 0.9800 . ?
C15 C7 1.368(2) . ?
C15 C16 1.484(3) . ?
C8 C13 1.405(3) . ?
C8 C9 1.409(3) . ?
C8 C7 1.426(3) . ?
C17 C22 1.375(3) . ?
C17 C18 1.377(3) . ?
C13 C12 1.386(3) . ?
C7 C6 1.491(3) . ?
C24 C25 1.388(3) . ?
C24 H24 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C16 H16 0.9800 . ?
C9 C10 1.374(3) . ?
C9 H9 0.9300 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 C11 1.367(3) . ?
C12 H12 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C28 C27 1.384(3) . ?
C28 H28 0.9300 . ?
C25 C26 1.355(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(4) . ?
C26 H26 0.9300 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C20 C21 1.353(4) . ?
C20 H20 0.9300 . ?
C22 C21 1.371(3) . ?
C22 H22 0.9300 . ?
C27 H27 0.9300 . ?
C21 H21 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
C16 O1 C2 109.10(12) . . ?
C15 N14 C13 108.97(14) . . ?
C15 N14 H14 125.5 . . ?
C13 N14 H14 125.5 . . ?
C16 N4 C3 104.45(13) . . ?
C16 N4 C5 112.23(15) . . ?
C3 N4 C5 115.87(15) . . ?
C24 C23 C28 118.40(18) . . ?
C24 C23 C2 120.00(17) . . ?
C28 C23 C2 121.55(17) . . ?
O1 C2 C23 111.13(14) . . ?
O1 C2 C3 104.17(13) . . ?
C23 C2 C3 114.43(14) . . ?
O1 C2 H2 109.0 . . ?
C23 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
N4 C3 C17 113.88(14) . . ?
N4 C3 C2 100.37(13) . . ?
C17 C3 C2 112.82(15) . . ?
N4 C3 H3 109.8 . . ?
C17 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C7 C15 N14 109.47(17) . . ?
C7 C15 C16 124.98(17) . . ?
N14 C15 C16 125.54(15) . . ?
C13 C8 C9 118.1(2) . . ?
C13 C8 C7 107.30(17) . . ?
C9 C8 C7 134.59(19) . . ?
C22 C17 C18 117.59(19) . . ?
C22 C17 C3 121.67(17) . . ?
C18 C17 C3 120.70(16) . . ?
N14 C13 C12 130.50(18) . . ?
N14 C13 C8 107.28(17) . . ?
C12 C13 C8 122.19(19) . . ?
C15 C7 C8 106.94(16) . . ?
C15 C7 C6 121.55(19) . . ?
C8 C7 C6 131.40(17) . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C17 C18 C19 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
O1 C16 N4 104.37(14) . . ?
O1 C16 C15 111.26(15) . . ?
N4 C16 C15 111.61(15) . . ?
O1 C16 H16 109.8 . . ?
N4 C16 H16 109.8 . . ?
C15 C16 H16 109.8 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N4 C5 C6 115.22(15) . . ?
N4 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
N4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C11 C12 C13 117.7(2) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C7 C6 C5 110.11(17) . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C23 C28 C27 120.1(2) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C26 C25 C24 119.9(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 121.9(2) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C21 C20 C19 119.1(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C21 C22 C17 121.1(2) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C26 C27 C28 120.7(2) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        64.81
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pavan
_database_code_depnum_ccdc_archive 'CCDC 1061479'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21.33 H13.33 Br2.67 N0.67 O0.67'
_chemical_formula_weight         502.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   16.2330(9)
_cell_length_b                   8.9312(7)
_cell_length_c                   19.8754(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.060(3)
_cell_angle_gamma                90.00
_cell_volume                     2769.1(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    7.305
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37199
_diffrn_reflns_av_R_equivalents  0.1512
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         64.49
_reflns_number_total             4593
_reflns_number_gt                2774
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1334P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0051(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br17 Br -0.07320(7) 0.03042(15) 0.32875(6) 0.0857(5) Uani 1 1 d . . .
Br24 Br -0.01242(6) 0.59809(15) 0.31308(6) 0.0885(5) Uani 1 1 d . . .
Br38 Br 0.85096(6) 0.06313(16) 0.73937(6) 0.0925(5) Uani 1 1 d . . .
Br31 Br 0.72099(7) 0.27341(19) 0.31337(6) 0.1047(6) Uani 1 1 d . . .
O4 O 0.3909(4) 0.3276(8) 0.4587(3) 0.0707(16) Uani 1 1 d . . .
N1 N 0.4212(3) 0.2290(7) 0.5945(3) 0.0495(15) Uani 1 1 d . . .
C25 C 0.5328(4) 0.2695(9) 0.4542(4) 0.0490(18) Uani 1 1 d . . .
C3 C 0.4694(4) 0.2714(9) 0.4950(4) 0.0488(18) Uani 1 1 d . . .
C19 C 0.2042(4) 0.3370(10) 0.3819(4) 0.055(2) Uani 1 1 d . . .
H19 H 0.2278 0.2549 0.3652 0.066 Uiso 1 1 calc R . .
C5 C 0.3277(4) 0.3312(9) 0.4888(4) 0.0470(18) Uani 1 1 d . . .
C18 C 0.2463(4) 0.3986(9) 0.4462(4) 0.0468(17) Uani 1 1 d . . .
C32 C 0.5747(4) 0.1845(9) 0.6084(4) 0.0488(19) Uani 1 1 d . . .
C6 C 0.3379(4) 0.2753(9) 0.5571(4) 0.0489(18) Uani 1 1 d . . .
C11 C 0.1278(4) 0.2201(10) 0.5263(4) 0.055(2) Uani 1 1 d . . .
C33 C 0.5919(5) 0.0430(9) 0.6388(4) 0.0521(19) Uani 1 1 d . . .
H33 H 0.5482 -0.0274 0.6328 0.062 Uiso 1 1 calc R . .
C23 C 0.2122(5) 0.5252(10) 0.4695(4) 0.055(2) Uani 1 1 d . . .
H23 H 0.2409 0.5689 0.5120 0.065 Uiso 1 1 calc R . .
C2 C 0.4880(4) 0.2274(9) 0.5632(4) 0.0462(17) Uani 1 1 d . . .
C36 C 0.7231(5) 0.2507(10) 0.6580(4) 0.055(2) Uani 1 1 d . . .
H36 H 0.7673 0.3201 0.6643 0.066 Uiso 1 1 calc R . .
C22 C 0.1358(5) 0.5865(10) 0.4299(4) 0.059(2) Uani 1 1 d . . .
H22 H 0.1130 0.6709 0.4456 0.071 Uiso 1 1 calc R . .
C37 C 0.6411(5) 0.2865(10) 0.6190(4) 0.0531(19) Uani 1 1 d . . .
H37 H 0.6303 0.3815 0.5994 0.064 Uiso 1 1 calc R . .
C15 C -0.0113(5) 0.2335(11) 0.4421(5) 0.067(2) Uani 1 1 d . . .
H15 H -0.0633 0.2827 0.4242 0.080 Uiso 1 1 calc R . .
C30 C 0.5289(5) 0.3830(10) 0.4045(4) 0.055(2) Uani 1 1 d . . .
H30 H 0.4881 0.4582 0.3995 0.066 Uiso 1 1 calc R . .
C7 C 0.2835(5) 0.2549(10) 0.6014(4) 0.056(2) Uani 1 1 d . . .
C27 C 0.6490(5) 0.1589(11) 0.4179(4) 0.064(2) Uani 1 1 d . . .
H27 H 0.6894 0.0832 0.4222 0.077 Uiso 1 1 calc R . .
C20 C 0.1273(5) 0.3965(11) 0.3423(4) 0.063(2) Uani 1 1 d . . .
H20 H 0.0986 0.3531 0.2997 0.076 Uiso 1 1 calc R . .
C34 C 0.6745(6) 0.0081(11) 0.6781(4) 0.064(2) Uani 1 1 d . . .
H34 H 0.6864 -0.0861 0.6984 0.077 Uiso 1 1 calc R . .
C10 C 0.1906(5) 0.2891(11) 0.5890(4) 0.060(2) Uani 1 1 d . . .
H10A H 0.1838 0.3969 0.5851 0.073 Uiso 1 1 calc R . .
H10B H 0.1742 0.2586 0.6303 0.073 Uiso 1 1 calc R . .
C26 C 0.5942(5) 0.1571(10) 0.4596(4) 0.059(2) Uani 1 1 d . . .
H26 H 0.5981 0.0801 0.4919 0.071 Uiso 1 1 calc R . .
C21 C 0.0935(5) 0.5207(10) 0.3665(5) 0.060(2) Uani 1 1 d . . .
C12 C 0.1434(5) 0.0910(11) 0.4928(5) 0.064(2) Uani 1 1 d . . .
H12 H 0.1959 0.0428 0.5096 0.077 Uiso 1 1 calc R . .
C8 C 0.3390(5) 0.2028(11) 0.6651(4) 0.064(2) Uani 1 1 d . . .
H8 H 0.3220 0.1831 0.7052 0.077 Uiso 1 1 calc R . .
C14 C 0.0075(5) 0.1028(11) 0.4112(4) 0.061(2) Uani 1 1 d . . .
C28 C 0.6445(5) 0.2725(11) 0.3697(4) 0.061(2) Uani 1 1 d . . .
C16 C 0.0479(5) 0.2868(11) 0.4986(5) 0.066(2) Uani 1 1 d . . .
H16 H 0.0348 0.3724 0.5203 0.079 Uiso 1 1 calc R . .
C13 C 0.0849(6) 0.0332(11) 0.4366(5) 0.068(2) Uani 1 1 d . . .
H13 H 0.0972 -0.0535 0.4154 0.081 Uiso 1 1 calc R . .
C35 C 0.7380(5) 0.1116(10) 0.6870(4) 0.056(2) Uani 1 1 d . . .
C9 C 0.4201(5) 0.1850(11) 0.6601(4) 0.061(2) Uani 1 1 d . . .
H9 H 0.4666 0.1494 0.6951 0.073 Uiso 1 1 calc R . .
C29 C 0.5847(5) 0.3854(11) 0.3627(4) 0.061(2) Uani 1 1 d . . .
H29 H 0.5818 0.4620 0.3304 0.074 Uiso 1 1 calc R . .


_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
Br17 C14 1.906(9) . ?
Br24 C21 1.885(8) . ?
Br38 C35 1.891(7) . ?
Br31 C28 1.888(8) . ?
O4 C5 1.324(9) . ?
O4 C3 1.375(9) . ?
N1 C9 1.367(10) . ?
N1 C2 1.390(9) . ?
N1 C6 1.413(9) . ?
C25 C26 1.398(11) . ?
C25 C30 1.405(12) . ?
C25 C3 1.477(10) . ?
C3 C2 1.362(11) . ?
C19 C20 1.384(11) . ?
C19 C18 1.385(11) . ?
C19 H19 0.9300 . ?
C5 C6 1.413(11) . ?
C5 C18 1.486(10) . ?
C18 C23 1.394(11) . ?
C32 C37 1.383(11) . ?
C32 C33 1.395(12) . ?
C32 C2 1.494(10) . ?
C6 C7 1.419(10) . ?
C11 C12 1.390(13) . ?
C11 C16 1.395(11) . ?
C11 C10 1.506(12) . ?
C33 C34 1.388(11) . ?
C33 H33 0.9300 . ?
C23 C22 1.384(11) . ?
C23 H23 0.9300 . ?
C36 C35 1.363(12) . ?
C36 C37 1.379(10) . ?
C36 H36 0.9300 . ?
C22 C21 1.388(12) . ?
C22 H22 0.9300 . ?
C37 H37 0.9300 . ?
C15 C16 1.347(13) . ?
C15 C14 1.393(13) . ?
C15 H15 0.9300 . ?
C30 C29 1.388(11) . ?
C30 H30 0.9300 . ?
C7 C8 1.413(12) . ?
C7 C10 1.491(11) . ?
C27 C26 1.373(11) . ?
C27 C28 1.385(13) . ?
C27 H27 0.9300 . ?
C20 C21 1.382(12) . ?
C20 H20 0.9300 . ?
C34 C35 1.360(13) . ?
C34 H34 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C26 H26 0.9300 . ?
C12 C13 1.353(13) . ?
C12 H12 0.9300 . ?
C8 C9 1.356(11) . ?
C8 H8 0.9300 . ?
C14 C13 1.366(12) . ?
C28 C29 1.379(12) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C9 H9 0.9300 . ?
C29 H29 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
C5 O4 C3 119.5(6) . . ?
C9 N1 C2 129.9(6) . . ?
C9 N1 C6 108.7(6) . . ?
C2 N1 C6 121.3(6) . . ?
C26 C25 C30 117.7(7) . . ?
C26 C25 C3 123.8(7) . . ?
C30 C25 C3 118.4(7) . . ?
C2 C3 O4 123.1(7) . . ?
C2 C3 C25 123.2(6) . . ?
O4 C3 C25 113.6(6) . . ?
C20 C19 C18 120.7(8) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O4 C5 C6 121.9(6) . . ?
O4 C5 C18 115.5(6) . . ?
C6 C5 C18 122.7(6) . . ?
C19 C18 C23 119.3(7) . . ?
C19 C18 C5 120.0(7) . . ?
C23 C18 C5 120.8(7) . . ?
C37 C32 C33 118.5(7) . . ?
C37 C32 C2 119.2(7) . . ?
C33 C32 C2 122.3(7) . . ?
C5 C6 N1 116.6(6) . . ?
C5 C6 C7 135.6(6) . . ?
N1 C6 C7 107.8(6) . . ?
C12 C11 C16 116.0(8) . . ?
C12 C11 C10 124.3(7) . . ?
C16 C11 C10 119.6(8) . . ?
C34 C33 C32 119.6(8) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C22 C23 C18 120.5(7) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C3 C2 N1 117.1(6) . . ?
C3 C2 C32 125.8(6) . . ?
N1 C2 C32 117.0(6) . . ?
C35 C36 C37 118.7(8) . . ?
C35 C36 H36 120.7 . . ?
C37 C36 H36 120.7 . . ?
C23 C22 C21 119.2(8) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C36 C37 C32 121.6(8) . . ?
C36 C37 H37 119.2 . . ?
C32 C37 H37 119.2 . . ?
C16 C15 C14 118.1(8) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C29 C30 C25 121.5(8) . . ?
C29 C30 H30 119.3 . . ?
C25 C30 H30 119.3 . . ?
C8 C7 C6 104.3(7) . . ?
C8 C7 C10 125.4(7) . . ?
C6 C7 C10 130.2(7) . . ?
C26 C27 C28 120.5(8) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C21 C20 C19 119.5(8) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C35 C34 C33 120.0(8) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C7 C10 C11 118.4(7) . . ?
C7 C10 H10A 107.7 . . ?
C11 C10 H10A 107.7 . . ?
C7 C10 H10B 107.7 . . ?
C11 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?
C27 C26 C25 120.8(8) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C20 C21 C22 120.8(7) . . ?
C20 C21 Br24 119.1(6) . . ?
C22 C21 Br24 120.0(6) . . ?
C13 C12 C11 122.2(8) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C9 C8 C7 111.3(7) . . ?
C9 C8 H8 124.3 . . ?
C7 C8 H8 124.3 . . ?
C13 C14 C15 120.7(8) . . ?
C13 C14 Br17 120.4(7) . . ?
C15 C14 Br17 118.7(6) . . ?
C29 C28 C27 120.4(7) . . ?
C29 C28 Br31 119.8(7) . . ?
C27 C28 Br31 119.8(6) . . ?
C15 C16 C11 123.3(9) . . ?
C15 C16 H16 118.4 . . ?
C11 C16 H16 118.4 . . ?
C12 C13 C14 119.7(9) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C34 C35 C36 121.7(7) . . ?
C34 C35 Br38 120.1(7) . . ?
C36 C35 Br38 118.3(6) . . ?
C8 C9 N1 107.8(7) . . ?
C8 C9 H9 126.1 . . ?
N1 C9 H9 126.1 . . ?
C28 C29 C30 119.1(8) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        64.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.203
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pm2
_database_code_depnum_ccdc_archive 'CCDC 1061480'
_audit_update_record             
;
2015-04-23 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Br2 N O'
_chemical_formula_weight         485.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.5356(12)
_cell_length_b                   10.6128(14)
_cell_length_c                   19.707(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.537(4)
_cell_angle_gamma                90.00
_cell_volume                     1966.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      64.41

_exptl_crystal_description       Needle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    5.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2983
_exptl_absorpt_correction_T_max  0.3498
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9666
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0959
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         64.41
_reflns_number_total             3188
_reflns_number_gt                2505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.0965P)²+1.5576P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.45735(5) 0.91364(6) 0.61572(3) 0.0581(3) Uani 1 1 d . . .
Br20 Br 0.47935(6) 0.51105(7) 0.60048(3) 0.0678(3) Uani 1 1 d . . .
O4 O 0.8620(3) 0.7922(3) 0.74458(14) 0.0394(8) Uani 1 1 d . . .
N1 N 0.7600(3) 0.6340(4) 0.80049(17) 0.0370(9) Uani 1 1 d . . .
C3 C 0.7229(4) 0.7759(4) 0.7052(2) 0.0352(10) Uani 1 1 d . . .
H3 H 0.6605 0.8425 0.7176 0.042 Uiso 1 1 calc R . .
C14 C 0.5145(4) 0.6434(5) 0.7305(2) 0.0390(11) Uani 1 1 d . . .
C21 C 0.7234(4) 0.7810(4) 0.6298(2) 0.0374(10) Uani 1 1 d . . .
C2 C 0.6737(4) 0.6462(5) 0.7313(2) 0.0380(10) Uani 1 1 d . . .
H2 H 0.6995 0.5788 0.7018 0.046 Uiso 1 1 calc R . .
C22 C 0.6136(4) 0.8336(5) 0.5835(2) 0.0426(11) Uani 1 1 d . . .
C19 C 0.4194(4) 0.5925(5) 0.6764(2) 0.0474(12) Uani 1 1 d . . .
C15 C 0.4603(5) 0.6991(5) 0.7838(2) 0.0503(13) Uani 1 1 d . . .
H15 H 0.5227 0.7318 0.8209 0.060 Uiso 1 1 calc R . .
C5 C 0.8383(4) 0.7516(5) 0.8114(2) 0.0367(10) Uani 1 1 d . . .
H5 H 0.7754 0.8136 0.8278 0.044 Uiso 1 1 calc R . .
C25 C 0.8358(6) 0.7229(6) 0.5325(3) 0.0579(15) Uani 1 1 d . . .
H25 H 0.9101 0.6844 0.5153 0.069 Uiso 1 1 calc R . .
C23 C 0.6116(5) 0.8340(6) 0.5134(2) 0.0544(13) Uani 1 1 d . . .
H23 H 0.5365 0.8706 0.4839 0.065 Uiso 1 1 calc R . .
C26 C 0.8350(5) 0.7258(5) 0.6026(3) 0.0497(12) Uani 1 1 d . . .
H26 H 0.9106 0.6902 0.6323 0.060 Uiso 1 1 calc R . .
C6 C 0.9742(4) 0.7486(5) 0.86274(19) 0.0387(10) Uani 1 1 d . . .
C17 C 0.2220(5) 0.6577(7) 0.7288(3) 0.0735(19) Uani 1 1 d . . .
H17 H 0.1245 0.6625 0.7285 0.088 Uiso 1 1 calc R . .
C24 C 0.7237(7) 0.7785(6) 0.4878(3) 0.0660(18) Uani 1 1 d . . .
H24 H 0.7243 0.7784 0.4406 0.079 Uiso 1 1 calc R . .
C16 C 0.3154(5) 0.7074(6) 0.7834(3) 0.0670(18) Uani 1 1 d . . .
H16 H 0.2810 0.7461 0.8197 0.080 Uiso 1 1 calc R . .
C11 C 1.0231(4) 0.6376(6) 0.8951(2) 0.0481(13) Uani 1 1 d . . .
C18 C 0.2730(5) 0.6007(6) 0.6744(3) 0.0681(17) Uani 1 1 d . . .
H18 H 0.2105 0.5685 0.6371 0.082 Uiso 1 1 calc R . .
C7 C 1.0440(4) 0.8624(6) 0.8807(2) 0.0491(13) Uani 1 1 d . . .
H7 H 1.0115 0.9364 0.8583 0.059 Uiso 1 1 calc R . .
C13 C 0.8577(5) 0.5250(5) 0.8046(3) 0.0503(12) Uani 1 1 d . . .
H13A H 0.9205 0.5344 0.7709 0.060 Uiso 1 1 calc R . .
H13B H 0.8034 0.4481 0.7943 0.060 Uiso 1 1 calc R . .
C12 C 0.9457(5) 0.5166(6) 0.8767(3) 0.0614(15) Uani 1 1 d . . .
H12A H 0.8835 0.4989 0.9098 0.074 Uiso 1 1 calc R . .
H12B H 1.0135 0.4482 0.8783 0.074 Uiso 1 1 calc R . .
C10 C 1.1452(5) 0.6432(7) 0.9469(3) 0.0611(16) Uani 1 1 d . . .
H10 H 1.1803 0.5698 0.9693 0.073 Uiso 1 1 calc R . .
C8 C 1.1626(5) 0.8642(7) 0.9325(3) 0.0595(15) Uani 1 1 d . . .
H8 H 1.2084 0.9400 0.9453 0.071 Uiso 1 1 calc R . .
C9 C 1.2118(5) 0.7550(7) 0.9643(3) 0.0638(16) Uani 1 1 d . . .
H9 H 1.2919 0.7569 0.9984 0.077 Uiso 1 1 calc R . .


_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
Br01 C22 1.912(4) . ?
Br20 C19 1.897(5) . ?
O4 C3 1.432(4) . ?
O4 C5 1.439(5) . ?
N1 C5 1.452(6) . ?
N1 C2 1.476(5) . ?
N1 C13 1.479(6) . ?
C3 C21 1.488(5) . ?
C3 C2 1.568(6) . ?
C3 H3 0.9800 . ?
C14 C15 1.379(7) . ?
C14 C19 1.389(6) . ?
C14 C2 1.516(5) . ?
C21 C22 1.387(6) . ?
C21 C26 1.398(6) . ?
C2 H2 0.9800 . ?
C22 C23 1.378(6) . ?
C19 C18 1.393(6) . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C5 C6 1.506(5) . ?
C5 H5 0.9800 . ?
C25 C26 1.383(7) . ?
C25 C24 1.399(9) . ?
C25 H25 0.9300 . ?
C23 C24 1.386(8) . ?
C23 H23 0.9300 . ?
C26 H26 0.9300 . ?
C6 C11 1.383(7) . ?
C6 C7 1.396(7) . ?
C17 C16 1.383(9) . ?
C17 C18 1.388(9) . ?
C17 H17 0.9300 . ?
C24 H24 0.9300 . ?
C16 H16 0.9300 . ?
C11 C10 1.416(7) . ?
C11 C12 1.496(8) . ?
C18 H18 0.9300 . ?
C7 C8 1.391(6) . ?
C7 H7 0.9300 . ?
C13 C12 1.528(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 C9 1.362(9) . ?
C10 H10 0.9300 . ?
C8 C9 1.364(9) . ?
C8 H8 0.9300 . ?
C9 H9 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
C3 O4 C5 100.8(3) . . ?
C5 N1 C2 104.8(3) . . ?
C5 N1 C13 111.1(3) . . ?
C2 N1 C13 111.7(3) . . ?
O4 C3 C21 112.4(3) . . ?
O4 C3 C2 103.2(3) . . ?
C21 C3 C2 114.2(4) . . ?
O4 C3 H3 108.9 . . ?
C21 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
C15 C14 C19 118.2(4) . . ?
C15 C14 C2 119.0(4) . . ?
C19 C14 C2 122.8(4) . . ?
C22 C21 C26 117.1(4) . . ?
C22 C21 C3 123.0(4) . . ?
C26 C21 C3 119.8(4) . . ?
N1 C2 C14 114.3(3) . . ?
N1 C2 C3 103.2(3) . . ?
C14 C2 C3 111.5(4) . . ?
N1 C2 H2 109.2 . . ?
C14 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C23 C22 C21 122.9(4) . . ?
C23 C22 Br01 116.7(4) . . ?
C21 C22 Br01 120.3(3) . . ?
C14 C19 C18 121.5(5) . . ?
C14 C19 Br20 122.6(3) . . ?
C18 C19 Br20 115.9(4) . . ?
C14 C15 C16 121.6(5) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
O4 C5 N1 106.0(3) . . ?
O4 C5 C6 111.9(3) . . ?
N1 C5 C6 116.5(4) . . ?
O4 C5 H5 107.3 . . ?
N1 C5 H5 107.3 . . ?
C6 C5 H5 107.3 . . ?
C26 C25 C24 119.4(5) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C22 C23 C24 118.8(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C25 C26 C21 121.5(5) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C11 C6 C7 120.6(4) . . ?
C11 C6 C5 121.0(4) . . ?
C7 C6 C5 118.2(4) . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C17 C16 C15 119.6(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C6 C11 C10 118.1(5) . . ?
C6 C11 C12 120.2(4) . . ?
C10 C11 C12 121.7(5) . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
N1 C13 C12 109.9(4) . . ?
N1 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
N1 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C11 C12 C13 110.4(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C9 C10 C11 120.8(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        64.41
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         1.233
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.145
