# Electronic Supplementary Material (ESI) for ChemComm.
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 1057577'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H25 N O3'
_chemical_formula_weight         483.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   15.116(2)
_cell_length_b                   11.4640(17)
_cell_length_c                   15.484(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.324(3)
_cell_angle_gamma                90.00
_cell_volume                     2587.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1508
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      20.01

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            14072
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4568
_reflns_number_gt                2490
_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)+(0.0765P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0063(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
N1 N 0.88931(14) 1.13680(18) 1.01651(15) 0.0536(6) Uani 1 1 d . A 1
O1 O 0.84786(13) 0.98335(16) 0.91783(13) 0.0648(6) Uani 1 1 d . A 1
O2 O 0.76603(12) 0.90662(14) 1.05838(11) 0.0547(5) Uani 1 1 d . A 1
O3 O 0.48126(13) 0.95760(17) 0.87247(14) 0.0711(6) Uani 1 1 d . A 1
C1 C 0.86463(18) 1.1761(2) 1.09347(18) 0.0491(7) Uani 1 1 d . A 1
C2 C 0.79182(17) 1.1107(2) 1.10525(17) 0.0464(7) Uani 1 1 d . A 1
C3 C 0.7575(2) 1.1305(2) 1.17833(18) 0.0589(8) Uani 1 1 d . A 1
H3 H 0.7088 1.0868 1.1871 0.071 Uiso 1 1 calc R A 1
C4 C 0.7978(2) 1.2174(3) 1.2381(2) 0.0707(9) Uani 1 1 d . A 1
H4 H 0.7755 1.2324 1.2875 0.085 Uiso 1 1 calc R A 1
C5 C 0.8703(2) 1.2818(3) 1.2256(2) 0.0752(10) Uani 1 1 d . A 1
H5 H 0.8963 1.3394 1.2668 0.090 Uiso 1 1 calc R A 1
C6 C 0.9051(2) 1.2623(2) 1.1527(2) 0.0639(8) Uani 1 1 d . A 1
H6 H 0.9540 1.3057 1.1440 0.077 Uiso 1 1 calc R A 1
C7 C 0.76173(17) 1.0272(2) 1.02888(17) 0.0471(7) Uani 1 1 d . A 1
C8 C 0.83665(18) 1.0437(2) 0.97895(18) 0.0497(7) Uani 1 1 d . A 1
C12 C 0.66157(17) 1.0438(2) 0.96930(17) 0.0488(7) Uani 1 1 d . A 1
H12 H 0.6243 1.0739 1.0074 0.059 Uiso 1 1 calc R A 1
C13 C 0.63414(17) 0.9182(2) 0.94660(16) 0.0462(6) Uani 1 1 d . A 1
C14 C 0.69333(17) 0.8485(2) 1.00304(17) 0.0464(6) Uani 1 1 d . A 1
C15 C 0.65404(17) 1.1279(2) 0.89324(19) 0.0530(7) Uani 1 1 d . A 1
C16 C 0.6414(2) 1.2451(3) 0.9071(2) 0.0792(10) Uani 1 1 d . A 1
H16 H 0.6339 1.2694 0.9620 0.095 Uiso 1 1 calc R A 1
C17 C 0.6398(3) 1.3261(3) 0.8421(3) 0.1066(14) Uani 1 1 d . A 1
H17 H 0.6317 1.4045 0.8534 0.128 Uiso 1 1 calc R A 1
C18 C 0.6498(2) 1.2926(4) 0.7604(3) 0.0931(12) Uani 1 1 d . A 1
H18 H 0.6490 1.3480 0.7163 0.112 Uiso 1 1 calc R A 1
C19 C 0.6611(2) 1.1766(3) 0.7439(2) 0.0802(10) Uani 1 1 d . A 1
H19 H 0.6674 1.1530 0.6883 0.096 Uiso 1 1 calc R A 1
C20 C 0.66310(19) 1.0947(3) 0.8106(2) 0.0644(8) Uani 1 1 d . A 1
H20 H 0.6707 1.0162 0.7992 0.077 Uiso 1 1 calc R A 1
C21 C 0.54562(19) 0.8885(2) 0.88437(17) 0.0505(7) Uani 1 1 d . A 1
C22 C 0.53515(18) 0.7767(2) 0.83345(16) 0.0475(7) Uani 1 1 d . A 1
C23 C 0.4497(2) 0.7233(3) 0.8087(2) 0.0671(8) Uani 1 1 d . A 1
H23 H 0.4007 0.7567 0.8255 0.081 Uiso 1 1 calc R A 1
C24 C 0.4366(2) 0.6215(3) 0.7598(2) 0.0773(10) Uani 1 1 d . A 1
H24 H 0.3794 0.5857 0.7444 0.093 Uiso 1 1 calc R A 1
C25 C 0.5089(3) 0.5730(3) 0.7337(2) 0.0761(10) Uani 1 1 d . A 1
H25 H 0.5003 0.5045 0.7004 0.091 Uiso 1 1 calc R A 1
C26 C 0.5931(2) 0.6252(3) 0.7567(2) 0.0691(9) Uani 1 1 d . A 1
H26 H 0.6415 0.5925 0.7384 0.083 Uiso 1 1 calc R A 1
C27 C 0.6067(2) 0.7267(2) 0.80701(18) 0.0569(7) Uani 1 1 d . A 1
H27 H 0.6644 0.7612 0.8231 0.068 Uiso 1 1 calc R A 1
C28 C 0.6952(2) 0.7226(2) 1.02370(17) 0.0536(7) Uani 1 1 d . A 1
C29 C 0.6181(2) 0.6631(3) 1.03082(19) 0.0705(9) Uani 1 1 d . A 1
H29 H 0.5617 0.7009 1.0186 0.085 Uiso 1 1 calc R A 1
C30 C 0.6250(3) 0.5470(3) 1.0562(2) 0.0913(12) Uani 1 1 d . A 1
H30 H 0.5727 0.5069 1.0603 0.110 Uiso 1 1 calc R A 1
C31 C 0.7063(4) 0.4912(3) 1.0751(2) 0.1004(14) Uani 1 1 d . A 1
H31 H 0.7100 0.4132 1.0924 0.121 Uiso 1 1 calc R A 1
C32 C 0.7831(3) 0.5487(3) 1.0690(3) 0.1065(13) Uani 1 1 d . A 1
H32 H 0.8392 0.5101 1.0820 0.128 Uiso 1 1 calc R A 1
C33 C 0.7779(3) 0.6646(3) 1.0434(2) 0.0837(11) Uani 1 1 d . A 1
H33 H 0.8307 0.7036 1.0395 0.100 Uiso 1 1 calc R A 1
C9 C 0.9658(2) 1.1822(3) 0.9865(2) 0.0718(9) Uani 1 1 d . A 1
H9A H 0.9813 1.1271 0.9453 0.086 Uiso 1 1 calc R A 1
H9B H 1.0187 1.1904 1.0376 0.086 Uiso 1 1 calc R A 1
C10 C 0.9441(4) 1.2980(4) 0.9411(3) 0.1004(13) Uani 1 1 d . A 1
H10A H 0.9513 1.2770 0.8820 0.120 Uiso 1 1 calc R A 1
C11A C 0.8813(6) 1.3521(7) 0.9198(5) 0.100(2) Uani 0.55 1 d P A 1
H11A H 0.8860 1.4329 0.9182 0.120 Uiso 0.55 1 calc PR A 1
H11B H 0.8239 1.3166 0.9036 0.120 Uiso 0.55 1 calc PR A 1
C11B C 0.9754(9) 1.3935(9) 0.9470(9) 0.162(5) Uani 0.45 1 d P A 1
H11C H 0.9367 1.4577 0.9327 0.194 Uiso 0.45 1 calc PR A 1
H11D H 1.0385 1.4041 0.9659 0.194 Uiso 0.45 1 calc PR A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.366(3) . ?
N1 C1 1.413(3) . ?
N1 C9 1.451(4) . ?
O1 C8 1.220(3) . ?
O2 C14 1.374(3) . ?
O2 C7 1.452(3) . ?
O3 C21 1.230(3) . ?
C1 C6 1.376(4) . ?
C1 C2 1.383(4) . ?
C2 C3 1.382(4) . ?
C2 C7 1.496(3) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.542(4) . ?
C7 C12 1.562(3) . ?
C12 C15 1.503(4) . ?
C12 C13 1.513(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.338(3) . ?
C13 C21 1.467(3) . ?
C14 C28 1.476(4) . ?
C15 C20 1.377(4) . ?
C15 C16 1.382(4) . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.492(4) . ?
C22 C27 1.379(4) . ?
C22 C23 1.389(4) . ?
C23 C24 1.377(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.379(4) . ?
C28 C33 1.378(4) . ?
C29 C30 1.384(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.348(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.360(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.382(4) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C9 C10 1.497(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11A 1.109(7) . ?
C10 C11B 1.187(10) . ?
C10 H10A 0.9800 . ?
C11A H11A 0.9300 . ?
C11A H11B 0.9300 . ?
C11B H11C 0.9300 . ?
C11B H11D 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
C8 N1 C1 110.7(2) . . ?
C8 N1 C9 124.6(2) . . ?
C1 N1 C9 124.4(2) . . ?
C14 O2 C7 107.69(18) . . ?
C6 C1 C2 122.0(3) . . ?
C6 C1 N1 128.4(3) . . ?
C2 C1 N1 109.6(2) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 C7 130.6(3) . . ?
C1 C2 C7 109.2(2) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
O2 C7 C2 112.44(19) . . ?
O2 C7 C8 107.3(2) . . ?
C2 C7 C8 102.0(2) . . ?
O2 C7 C12 104.90(19) . . ?
C2 C7 C12 115.7(2) . . ?
C8 C7 C12 114.5(2) . . ?
O1 C8 N1 126.1(3) . . ?
O1 C8 C7 126.2(2) . . ?
N1 C8 C7 107.8(2) . . ?
C15 C12 C13 118.0(2) . . ?
C15 C12 C7 113.7(2) . . ?
C13 C12 C7 100.66(19) . . ?
C15 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C7 C12 H12 108.0 . . ?
C14 C13 C21 128.8(2) . . ?
C14 C13 C12 108.8(2) . . ?
C21 C13 C12 121.3(2) . . ?
C13 C14 O2 113.8(2) . . ?
C13 C14 C28 134.2(2) . . ?
O2 C14 C28 111.9(2) . . ?
C20 C15 C16 117.7(3) . . ?
C20 C15 C12 123.0(2) . . ?
C16 C15 C12 119.2(3) . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 121.0(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
O3 C21 C13 119.8(2) . . ?
O3 C21 C22 120.3(2) . . ?
C13 C21 C22 119.8(2) . . ?
C27 C22 C23 118.7(3) . . ?
C27 C22 C21 122.2(2) . . ?
C23 C22 C21 119.1(3) . . ?
C24 C23 C22 120.9(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 120.3(3) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C33 118.7(3) . . ?
C29 C28 C14 122.2(3) . . ?
C33 C28 C14 118.9(3) . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 120.9(4) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C28 C33 C32 120.4(3) . . ?
C28 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
N1 C9 C10 112.0(3) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11A C10 C11B 78.4(8) . . ?
C11A C10 C9 134.4(6) . . ?
C11B C10 C9 138.5(9) . . ?
C11A C10 H10A 99.1 . . ?
C11B C10 H10A 99.1 . . ?
C9 C10 H10A 99.1 . . ?
C10 C11A H11A 120.0 . . ?
C10 C11A H11B 120.0 . . ?
H11A C11A H11B 120.0 . . ?
C10 C11B H11C 120.0 . . ?
C10 C11B H11D 120.0 . . ?
H11C C11B H11D 120.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.254
_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_shelxl_sqd
_database_code_depnum_ccdc_archive 'CCDC 1057578'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H22 Br N O3'
_chemical_formula_weight         536.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   15.016(3)
_cell_length_b                   11.906(2)
_cell_length_c                   15.221(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.25(3)
_cell_angle_gamma                90.00
_cell_volume                     2677.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6384
_cell_measurement_theta_min      1.3595
_cell_measurement_theta_max      27.8545

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7049
_exptl_absorpt_correction_T_max  0.7657
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
???? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            26056
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.01
_reflns_number_total             6429
_reflns_number_gt                5030
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0508P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6429
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.585944(16) 1.36983(2) 0.213277(17) 0.02167(10) Uani 1 1 d . . .
O1 O 0.66003(11) 0.95162(14) 0.59155(11) 0.0225(4) Uani 1 1 d . . .
O2 O 0.73933(11) 0.88137(12) 0.43901(11) 0.0168(4) Uani 1 1 d . . .
O3 O 1.01241(11) 0.92913(13) 0.61905(11) 0.0209(4) Uani 1 1 d . . .
N1 N 0.61523(13) 1.09790(16) 0.49445(13) 0.0182(4) Uani 1 1 d . . .
C1 C 0.64037(16) 1.13982(18) 0.41624(15) 0.0158(5) Uani 1 1 d . . .
C2 C 0.60094(15) 1.22677(19) 0.36339(16) 0.0186(5) Uani 1 1 d . . .
H2 H 0.5509 1.2675 0.3773 0.022 Uiso 1 1 calc R . .
C3 C 0.63862(15) 1.25152(19) 0.28839(15) 0.0176(5) Uani 1 1 d . . .
C4 C 0.71198(15) 1.1946(2) 0.26742(15) 0.0185(5) Uani 1 1 d . . .
H4 H 0.7358 1.2143 0.2157 0.022 Uiso 1 1 calc R . .
C5 C 0.75092(16) 1.1079(2) 0.32285(16) 0.0190(5) Uani 1 1 d . . .
H5 H 0.8020 1.0684 0.3098 0.023 Uiso 1 1 calc R . .
C6 C 0.71457(15) 1.08018(18) 0.39656(15) 0.0143(5) Uani 1 1 d . . .
C7 C 0.74346(15) 0.99746(18) 0.47022(15) 0.0153(5) Uani 1 1 d . . .
C8 C 0.66991(15) 1.01015(19) 0.52855(15) 0.0176(5) Uani 1 1 d . . .
C9 C 0.53782(18) 1.1365(2) 0.53015(19) 0.0270(6) Uani 1 1 d . . .
H9A H 0.5247 1.0832 0.5753 0.040 Uiso 1 1 calc R . .
H9B H 0.4853 1.1419 0.4819 0.040 Uiso 1 1 calc R . .
H9C H 0.5509 1.2105 0.5576 0.040 Uiso 1 1 calc R . .
C10 C 0.84157(15) 1.01230(18) 0.52196(15) 0.0159(5) Uani 1 1 d . . .
H10 H 0.8804 1.0363 0.4783 0.019 Uiso 1 1 calc R . .
C11 C 0.84858(15) 1.10119(19) 0.59399(16) 0.0167(5) Uani 1 1 d . . .
C12 C 0.83639(16) 1.0780(2) 0.68052(16) 0.0202(5) Uani 1 1 d . . .
H12 H 0.8258 1.0029 0.6971 0.024 Uiso 1 1 calc R . .
C13 C 0.83948(17) 1.1636(2) 0.74290(17) 0.0250(6) Uani 1 1 d . . .
H13 H 0.8313 1.1465 0.8019 0.030 Uiso 1 1 calc R . .
C14 C 0.85430(18) 1.2733(2) 0.71999(19) 0.0306(6) Uani 1 1 d . . .
H14 H 0.8562 1.3316 0.7629 0.037 Uiso 1 1 calc R . .
C15 C 0.86638(19) 1.2977(2) 0.63378(19) 0.0314(6) Uani 1 1 d . . .
H15 H 0.8762 1.3731 0.6174 0.038 Uiso 1 1 calc R . .
C16 C 0.86410(17) 1.2122(2) 0.57120(18) 0.0242(6) Uani 1 1 d . . .
H16 H 0.8732 1.2295 0.5125 0.029 Uiso 1 1 calc R . .
C17 C 0.86496(15) 0.89105(18) 0.54781(15) 0.0152(5) Uani 1 1 d . . .
C18 C 0.94897(16) 0.86240(18) 0.60872(15) 0.0152(5) Uani 1 1 d . . .
C19 C 0.95747(15) 0.75470(19) 0.65981(15) 0.0166(5) Uani 1 1 d . . .
C20 C 0.88315(17) 0.6980(2) 0.68114(16) 0.0205(5) Uani 1 1 d . . .
H20 H 0.8240 0.7279 0.6634 0.025 Uiso 1 1 calc R . .
C21 C 0.89517(19) 0.5981(2) 0.72812(17) 0.0260(6) Uani 1 1 d . . .
H21 H 0.8444 0.5598 0.7431 0.031 Uiso 1 1 calc R . .
C22 C 0.98191(19) 0.5536(2) 0.75359(17) 0.0276(6) Uani 1 1 d . . .
H22 H 0.9899 0.4834 0.7837 0.033 Uiso 1 1 calc R . .
C23 C 1.05609(19) 0.6114(2) 0.73511(18) 0.0274(6) Uani 1 1 d . . .
H23 H 1.1153 0.5823 0.7542 0.033 Uiso 1 1 calc R . .
C24 C 1.04419(16) 0.7112(2) 0.68898(16) 0.0222(5) Uani 1 1 d . . .
H24 H 1.0955 0.7511 0.6768 0.027 Uiso 1 1 calc R . .
C25 C 0.80771(15) 0.82455(19) 0.49329(15) 0.0157(5) Uani 1 1 d . . .
C26 C 0.80632(16) 0.70343(19) 0.47281(15) 0.0172(5) Uani 1 1 d . . .
C27 C 0.72431(17) 0.6458(2) 0.45731(17) 0.0229(5) Uani 1 1 d . . .
H27 H 0.6700 0.6838 0.4632 0.028 Uiso 1 1 calc R . .
C28 C 0.72142(18) 0.5335(2) 0.43336(18) 0.0286(6) Uani 1 1 d . . .
H28 H 0.6654 0.4944 0.4234 0.034 Uiso 1 1 calc R . .
C29 C 0.80051(19) 0.4782(2) 0.42400(18) 0.0300(6) Uani 1 1 d . . .
H29 H 0.7985 0.4014 0.4068 0.036 Uiso 1 1 calc R . .
C30 C 0.88201(18) 0.5344(2) 0.43957(17) 0.0269(6) Uani 1 1 d . . .
H30 H 0.9361 0.4959 0.4340 0.032 Uiso 1 1 calc R . .
C31 C 0.88543(17) 0.6471(2) 0.46336(16) 0.0214(5) Uani 1 1 d . . .
H31 H 0.9417 0.6858 0.4732 0.026 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
Br1 C3 1.896(2) . ?
O1 C8 1.216(3) . ?
O2 C25 1.376(3) . ?
O2 C7 1.459(3) . ?
O3 C18 1.229(3) . ?
N1 C8 1.372(3) . ?
N1 C1 1.403(3) . ?
N1 C9 1.443(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(3) . ?
C4 C5 1.395(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(3) . ?
C7 C8 1.543(3) . ?
C7 C10 1.552(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.514(3) . ?
C10 C17 1.521(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.389(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C25 1.342(3) . ?
C17 C18 1.467(3) . ?
C18 C19 1.493(3) . ?
C19 C20 1.391(3) . ?
C19 C24 1.398(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.475(3) . ?
C26 C27 1.393(3) . ?
C26 C31 1.394(3) . ?
C27 C28 1.384(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.378(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O2 C7 106.64(17) . . ?
C8 N1 C1 111.00(19) . . ?
C8 N1 C9 124.6(2) . . ?
C1 N1 C9 124.2(2) . . ?
C2 C1 C6 122.2(2) . . ?
C2 C1 N1 127.6(2) . . ?
C6 C1 N1 110.3(2) . . ?
C1 C2 C3 116.2(2) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 Br1 119.36(18) . . ?
C2 C3 Br1 117.69(17) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 C7 131.7(2) . . ?
C1 C6 C7 108.02(19) . . ?
O2 C7 C6 112.91(18) . . ?
O2 C7 C8 106.67(17) . . ?
C6 C7 C8 102.99(18) . . ?
O2 C7 C10 104.74(17) . . ?
C6 C7 C10 115.31(18) . . ?
C8 C7 C10 114.14(19) . . ?
O1 C8 N1 125.9(2) . . ?
O1 C8 C7 126.7(2) . . ?
N1 C8 C7 107.36(19) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C17 119.55(19) . . ?
C11 C10 C7 112.61(18) . . ?
C17 C10 C7 100.25(17) . . ?
C11 C10 H10 107.9 . . ?
C17 C10 H10 107.9 . . ?
C7 C10 H10 107.9 . . ?
C12 C11 C16 118.7(2) . . ?
C12 C11 C10 122.9(2) . . ?
C16 C11 C10 118.4(2) . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C25 C17 C18 129.6(2) . . ?
C25 C17 C10 107.9(2) . . ?
C18 C17 C10 121.15(19) . . ?
O3 C18 C17 119.4(2) . . ?
O3 C18 C19 119.7(2) . . ?
C17 C18 C19 120.9(2) . . ?
C20 C19 C24 119.1(2) . . ?
C20 C19 C18 122.7(2) . . ?
C24 C19 C18 118.1(2) . . ?
C21 C20 C19 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C17 C25 O2 114.13(19) . . ?
C17 C25 C26 133.7(2) . . ?
O2 C25 C26 111.90(19) . . ?
C27 C26 C31 119.3(2) . . ?
C27 C26 C25 119.8(2) . . ?
C31 C26 C25 120.8(2) . . ?
C28 C27 C26 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.9(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 120.3(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.0(2) . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?

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
C8 N1 C1 C2 179.6(2) . . . . ?
C9 N1 C1 C2 4.0(4) . . . . ?
C8 N1 C1 C6 -0.6(3) . . . . ?
C9 N1 C1 C6 -176.1(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
N1 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 Br1 179.55(17) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Br1 C3 C4 C5 179.76(18) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C7 -176.1(2) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
N1 C1 C6 C5 -179.5(2) . . . . ?
C2 C1 C6 C7 176.4(2) . . . . ?
N1 C1 C6 C7 -3.5(3) . . . . ?
C25 O2 C7 C6 147.88(18) . . . . ?
C25 O2 C7 C8 -99.7(2) . . . . ?
C25 O2 C7 C10 21.6(2) . . . . ?
C5 C6 C7 O2 -64.3(3) . . . . ?
C1 C6 C7 O2 120.2(2) . . . . ?
C5 C6 C7 C8 -179.0(2) . . . . ?
C1 C6 C7 C8 5.6(2) . . . . ?
C5 C6 C7 C10 56.0(3) . . . . ?
C1 C6 C7 C10 -119.4(2) . . . . ?
C1 N1 C8 O1 -173.9(2) . . . . ?
C9 N1 C8 O1 1.7(4) . . . . ?
C1 N1 C8 C7 4.2(3) . . . . ?
C9 N1 C8 C7 179.7(2) . . . . ?
O2 C7 C8 O1 53.0(3) . . . . ?
C6 C7 C8 O1 172.1(2) . . . . ?
C10 C7 C8 O1 -62.1(3) . . . . ?
O2 C7 C8 N1 -125.00(19) . . . . ?
C6 C7 C8 N1 -5.9(2) . . . . ?
C10 C7 C8 N1 119.8(2) . . . . ?
O2 C7 C10 C11 -152.73(18) . . . . ?
C6 C7 C10 C11 82.5(2) . . . . ?
C8 C7 C10 C11 -36.4(3) . . . . ?
O2 C7 C10 C17 -24.5(2) . . . . ?
C6 C7 C10 C17 -149.28(19) . . . . ?
C8 C7 C10 C17 91.7(2) . . . . ?
C17 C10 C11 C12 -29.0(3) . . . . ?
C7 C10 C11 C12 88.2(3) . . . . ?
C17 C10 C11 C16 153.9(2) . . . . ?
C7 C10 C11 C16 -88.9(3) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 C13 -177.0(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C11 0.8(4) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C10 C11 C16 C15 176.6(2) . . . . ?
C11 C10 C17 C25 143.2(2) . . . . ?
C7 C10 C17 C25 19.8(2) . . . . ?
C11 C10 C17 C18 -48.7(3) . . . . ?
C7 C10 C17 C18 -172.16(19) . . . . ?
C25 C17 C18 O3 144.2(2) . . . . ?
C10 C17 C18 O3 -21.0(3) . . . . ?
C25 C17 C18 C19 -37.3(4) . . . . ?
C10 C17 C18 C19 157.5(2) . . . . ?
O3 C18 C19 C20 153.1(2) . . . . ?
C17 C18 C19 C20 -25.4(3) . . . . ?
O3 C18 C19 C24 -25.3(3) . . . . ?
C17 C18 C19 C24 156.2(2) . . . . ?
C24 C19 C20 C21 -2.0(4) . . . . ?
C18 C19 C20 C21 179.6(2) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C23 2.6(4) . . . . ?
C21 C22 C23 C24 -2.1(4) . . . . ?
C22 C23 C24 C19 -0.5(4) . . . . ?
C20 C19 C24 C23 2.6(4) . . . . ?
C18 C19 C24 C23 -179.0(2) . . . . ?
C18 C17 C25 O2 -174.3(2) . . . . ?
C10 C17 C25 O2 -7.6(3) . . . . ?
C18 C17 C25 C26 -0.7(4) . . . . ?
C10 C17 C25 C26 166.0(2) . . . . ?
C7 O2 C25 C17 -9.4(2) . . . . ?
C7 O2 C25 C26 175.61(18) . . . . ?
C17 C25 C26 C27 143.2(3) . . . . ?
O2 C25 C26 C27 -43.2(3) . . . . ?
C17 C25 C26 C31 -40.8(4) . . . . ?
O2 C25 C26 C31 132.9(2) . . . . ?
C31 C26 C27 C28 0.4(4) . . . . ?
C25 C26 C27 C28 176.5(2) . . . . ?
C26 C27 C28 C29 -0.5(4) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C28 C29 C30 C31 -1.0(4) . . . . ?
C29 C30 C31 C26 0.9(4) . . . . ?
C27 C26 C31 C30 -0.6(4) . . . . ?
C25 C26 C31 C30 -176.7(2) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 154 49 ' '
2 0.500 0.500 0.500 154 49 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_zrr3
_database_code_depnum_ccdc_archive 'CCDC 1057579'
_audit_update_record             
;
2015-04-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N3 O3'
_chemical_formula_weight         433.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   21.917(6)
_cell_length_b                   9.529(2)
_cell_length_c                   23.123(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.112(4)
_cell_angle_gamma                90.00
_cell_volume                     4373(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            22685
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3880
_reflns_number_gt                2859
_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)+(0.0264P)²+2.9401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3880
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
N1 N 0.44875(7) 0.47961(14) 0.07253(7) 0.0541(4) Uani 1 1 d . . .
N2 N 0.33049(8) 0.06556(15) 0.05750(7) 0.0614(4) Uani 1 1 d . . .
N3 N 0.64576(9) 0.1984(2) 0.10174(9) 0.0868(6) Uani 1 1 d . . .
O1 O 0.51575(7) 0.43808(13) 0.17827(6) 0.0697(4) Uani 1 1 d . . .
O2 O 0.48479(6) 0.08421(12) 0.18107(5) 0.0558(3) Uani 1 1 d . . .
O3 O 0.42182(7) -0.06043(13) 0.06220(7) 0.0767(4) Uani 1 1 d . . .
C1 C 0.43100(8) 0.40560(17) 0.01536(8) 0.0496(4) Uani 1 1 d . . .
C2 C 0.44996(8) 0.26556(17) 0.02811(8) 0.0474(4) Uani 1 1 d . . .
C3 C 0.44057(9) 0.1755(2) -0.02136(8) 0.0592(5) Uani 1 1 d . . .
H3 H 0.4531 0.0817 -0.0134 0.071 Uiso 1 1 calc R . .
C4 C 0.41226(10) 0.2268(2) -0.08316(9) 0.0708(6) Uani 1 1 d . . .
H4 H 0.4059 0.1669 -0.1170 0.085 Uiso 1 1 calc R . .
C5 C 0.39346(10) 0.3645(3) -0.09508(10) 0.0740(6) Uani 1 1 d . . .
H5 H 0.3744 0.3965 -0.1370 0.089 Uiso 1 1 calc R . .
C6 C 0.40211(9) 0.4573(2) -0.04628(10) 0.0651(5) Uani 1 1 d . . .
H6 H 0.3890 0.5507 -0.0546 0.078 Uiso 1 1 calc R . .
C7 C 0.48072(8) 0.24494(16) 0.09966(8) 0.0468(4) Uani 1 1 d . . .
C8 C 0.48553(8) 0.39834(18) 0.12370(9) 0.0522(4) Uani 1 1 d . . .
C9 C 0.43561(10) 0.62790(18) 0.07653(11) 0.0771(6) Uani 1 1 d . . .
H9A H 0.4565 0.6574 0.1204 0.116 Uiso 1 1 calc R . .
H9B H 0.3879 0.6432 0.0597 0.116 Uiso 1 1 calc R . .
H9C H 0.4537 0.6811 0.0522 0.116 Uiso 1 1 calc R . .
C10 C 0.54684(8) 0.16711(17) 0.13204(8) 0.0505(4) Uani 1 1 d . . .
C11 C 0.54522(8) 0.08310(17) 0.17770(8) 0.0510(4) Uani 1 1 d . . .
C12 C 0.43656(8) 0.15480(16) 0.12497(7) 0.0472(4) Uani 1 1 d . . .
C13 C 0.39702(10) 0.03839(17) 0.07734(8) 0.0556(4) Uani 1 1 d . . .
C14 C 0.38229(8) 0.22824(16) 0.13641(8) 0.0479(4) Uani 1 1 d . . .
C15 C 0.32067(9) 0.17543(18) 0.09353(8) 0.0557(4) Uani 1 1 d . . .
C16 C 0.26105(10) 0.2255(2) 0.09141(11) 0.0773(6) Uani 1 1 d . . .
H16 H 0.2198 0.1914 0.0618 0.093 Uiso 1 1 calc R . .
C17 C 0.26438(11) 0.3286(2) 0.13480(12) 0.0855(7) Uani 1 1 d . . .
H17 H 0.2246 0.3653 0.1338 0.103 Uiso 1 1 calc R . .
C18 C 0.32483(11) 0.3778(2) 0.17907(11) 0.0755(6) Uani 1 1 d . . .
H18 H 0.3257 0.4450 0.2086 0.091 Uiso 1 1 calc R . .
C19 C 0.38489(9) 0.32819(19) 0.18034(9) 0.0600(5) Uani 1 1 d . . .
H19 H 0.4260 0.3618 0.2102 0.072 Uiso 1 1 calc R . .
C20 C 0.27787(11) -0.0296(2) 0.01639(11) 0.0931(7) Uani 1 1 d . . .
H20A H 0.2960 -0.0913 -0.0053 0.140 Uiso 1 1 calc R . .
H20B H 0.2415 0.0237 -0.0145 0.140 Uiso 1 1 calc R . .
H20C H 0.2615 -0.0840 0.0418 0.140 Uiso 1 1 calc R . .
C21 C 0.60209(9) 0.18404(19) 0.11610(9) 0.0597(5) Uani 1 1 d . . .
C22 C 0.59535(9) -0.01358(18) 0.22212(8) 0.0553(4) Uani 1 1 d . . .
C23 C 0.66293(10) 0.0181(2) 0.25011(10) 0.0782(6) Uani 1 1 d . . .
H23 H 0.6781 0.1038 0.2421 0.094 Uiso 1 1 calc R . .
C24 C 0.70841(12) -0.0790(3) 0.29048(12) 0.0978(8) Uani 1 1 d . . .
H24 H 0.7542 -0.0578 0.3098 0.117 Uiso 1 1 calc R . .
C25 C 0.68607(14) -0.2056(3) 0.30191(12) 0.0990(8) Uani 1 1 d . . .
H25 H 0.7168 -0.2701 0.3290 0.119 Uiso 1 1 calc R . .
C26 C 0.61914(13) -0.2381(3) 0.27396(12) 0.0918(7) Uani 1 1 d . . .
H26 H 0.6043 -0.3245 0.2817 0.110 Uiso 1 1 calc R . .
C27 C 0.57370(10) -0.1423(2) 0.23432(9) 0.0691(5) Uani 1 1 d . . .
H27 H 0.5280 -0.1641 0.2155 0.083 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
N1 C8 1.356(2) . ?
N1 C1 1.400(2) . ?
N1 C9 1.453(2) . ?
N2 C13 1.355(2) . ?
N2 C15 1.410(2) . ?
N2 C20 1.458(2) . ?
N3 C21 1.147(2) . ?
O1 C8 1.210(2) . ?
O2 C11 1.3593(19) . ?
O2 C12 1.4452(18) . ?
O3 C13 1.211(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.374(2) . ?
C2 C7 1.511(2) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.513(2) . ?
C7 C8 1.551(2) . ?
C7 C12 1.580(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.337(2) . ?
C10 C21 1.417(3) . ?
C11 C22 1.467(2) . ?
C12 C14 1.497(2) . ?
C12 C13 1.544(2) . ?
C14 C19 1.376(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.372(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C23 1.375(3) . ?
C22 C27 1.387(3) . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.364(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(3) . ?
C26 H26 0.9300 . ?
C27 H27 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
C8 N1 C1 111.11(14) . . ?
C8 N1 C9 124.07(17) . . ?
C1 N1 C9 124.54(16) . . ?
C13 N2 C15 110.73(14) . . ?
C13 N2 C20 122.79(17) . . ?
C15 N2 C20 124.77(17) . . ?
C11 O2 C12 108.14(12) . . ?
C6 C1 C2 121.68(17) . . ?
C6 C1 N1 128.08(16) . . ?
C2 C1 N1 110.17(14) . . ?
C3 C2 C1 119.78(16) . . ?
C3 C2 C7 132.07(15) . . ?
C1 C2 C7 108.12(14) . . ?
C2 C3 C4 118.88(18) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.60(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.30(18) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
C2 C7 C10 119.61(14) . . ?
C2 C7 C8 101.57(13) . . ?
C10 C7 C8 112.30(13) . . ?
C2 C7 C12 114.66(13) . . ?
C10 C7 C12 99.14(12) . . ?
C8 C7 C12 109.80(13) . . ?
O1 C8 N1 126.19(16) . . ?
O1 C8 C7 126.31(16) . . ?
N1 C8 C7 107.50(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C21 125.83(15) . . ?
C11 C10 C7 110.08(15) . . ?
C21 C10 C7 124.08(15) . . ?
C10 C11 O2 113.17(14) . . ?
C10 C11 C22 131.72(17) . . ?
O2 C11 C22 115.04(15) . . ?
O2 C12 C14 113.09(13) . . ?
O2 C12 C13 106.33(12) . . ?
C14 C12 C13 102.37(14) . . ?
O2 C12 C7 104.82(12) . . ?
C14 C12 C7 117.95(13) . . ?
C13 C12 C7 111.90(13) . . ?
O3 C13 N2 126.97(17) . . ?
O3 C13 C12 125.44(17) . . ?
N2 C13 C12 107.57(15) . . ?
C19 C14 C15 120.12(16) . . ?
C19 C14 C12 131.82(15) . . ?
C15 C14 C12 108.04(15) . . ?
C16 C15 C14 121.52(18) . . ?
C16 C15 N2 128.23(17) . . ?
C14 C15 N2 110.20(15) . . ?
C15 C16 C17 117.68(19) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 118.58(18) . . ?
C14 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C10 178.4(2) . . ?
C23 C22 C27 119.44(17) . . ?
C23 C22 C11 121.94(17) . . ?
C27 C22 C11 118.59(17) . . ?
C22 C23 C24 119.5(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.6(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 120.6(2) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.025
