# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_5c
_database_code_depnum_ccdc_archive 'CCDC 1483927'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         293.35

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   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   8.0476(5)
_cell_length_b                   8.1366(5)
_cell_length_c                   23.2624(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.493(2)
_cell_angle_gamma                90.00
_cell_volume                     1518.54(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_T_max  0.9644
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38076
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         26.39
_reflns_number_total             3106
_reflns_number_gt                2700
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0607P)²+0.5999P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3106
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 1.03011(11) 0.76512(11) 0.24884(4) 0.0281(2) Uani 1 1 d . . .
O2 O 0.81101(15) 0.70330(12) 0.03963(5) 0.0397(3) Uani 1 1 d . . .
N N 0.81892(12) 0.73883(12) 0.17557(4) 0.0218(2) Uani 1 1 d . . .
C1 C 0.74708(16) 0.90532(16) 0.17087(6) 0.0262(3) Uani 1 1 d . . .
H1A H 0.7261 0.9363 0.1298 0.031 Uiso 1 1 calc R . .
H1B H 0.8258 0.9858 0.1898 0.031 Uiso 1 1 calc R . .
C2 C 0.58518(16) 0.90630(18) 0.19988(6) 0.0295(3) Uani 1 1 d . . .
H2A H 0.5388 1.0191 0.1991 0.035 Uiso 1 1 calc R . .
H2B H 0.5035 0.8336 0.1784 0.035 Uiso 1 1 calc R . .
C3 C 0.61190(15) 0.84851(15) 0.26140(5) 0.0240(3) Uani 1 1 d . . .
C4 C 0.50359(17) 0.89319(18) 0.30291(6) 0.0310(3) Uani 1 1 d . . .
H4A H 0.4089 0.9591 0.2920 0.037 Uiso 1 1 calc R . .
C5 C 0.53258(18) 0.84265(19) 0.35957(6) 0.0354(3) Uani 1 1 d . . .
H5A H 0.4581 0.8742 0.3873 0.042 Uiso 1 1 calc R . .
C6 C 0.67033(19) 0.74579(17) 0.37597(6) 0.0337(3) Uani 1 1 d . . .
H6A H 0.6916 0.7128 0.4150 0.040 Uiso 1 1 calc R . .
C7 C 0.77613(17) 0.69769(16) 0.33514(6) 0.0278(3) Uani 1 1 d . . .
H7A H 0.8687 0.6290 0.3461 0.033 Uiso 1 1 calc R . .
C8 C 0.74847(15) 0.74891(14) 0.27793(5) 0.0216(3) Uani 1 1 d . . .
C9 C 0.86671(14) 0.69374(15) 0.23497(5) 0.0216(3) Uani 1 1 d . . .
H9A H 0.8770 0.5714 0.2372 0.026 Uiso 1 1 calc R . .
C10 C 1.11528(16) 0.73065(18) 0.19849(7) 0.0326(3) Uani 1 1 d . . .
H10A H 1.1745 0.6242 0.2025 0.039 Uiso 1 1 calc R . .
H10B H 1.1974 0.8181 0.1920 0.039 Uiso 1 1 calc R . .
C11 C 0.97785(16) 0.72427(16) 0.14763(6) 0.0267(3) Uani 1 1 d . . .
H11A H 0.9906 0.8198 0.1213 0.032 Uiso 1 1 calc R . .
C12 C 0.97794(17) 0.56483(17) 0.11358(6) 0.0302(3) Uani 1 1 d . . .
H12A H 1.0923 0.5423 0.1027 0.036 Uiso 1 1 calc R . .
H12B H 0.9446 0.4733 0.1382 0.036 Uiso 1 1 calc R . .
C13 C 0.86021(17) 0.57185(16) 0.05952(6) 0.0283(3) Uani 1 1 d . . .
C14 C 0.80374(17) 0.41538(16) 0.03049(6) 0.0281(3) Uani 1 1 d . . .
C15 C 0.8648(2) 0.26172(18) 0.04781(7) 0.0393(4) Uani 1 1 d . . .
H15A H 0.9486 0.2532 0.0788 0.047 Uiso 1 1 calc R . .
C16 C 0.8036(3) 0.1208(2) 0.01991(8) 0.0510(5) Uani 1 1 d . . .
H16A H 0.8466 0.0161 0.0314 0.061 Uiso 1 1 calc R . .
C17 C 0.6800(2) 0.1328(2) -0.02462(8) 0.0536(5) Uani 1 1 d . . .
H17A H 0.6367 0.0359 -0.0430 0.064 Uiso 1 1 calc R . .
C18 C 0.6189(3) 0.2842(2) -0.04271(8) 0.0523(5) Uani 1 1 d . . .
H18A H 0.5348 0.2920 -0.0736 0.063 Uiso 1 1 calc R . .
C19 C 0.6814(2) 0.42457(19) -0.01528(6) 0.0389(4) Uani 1 1 d . . .
H19A H 0.6403 0.5290 -0.0279 0.047 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 C10 1.4305(17) . ?
O1 C9 1.4506(14) . ?
O2 C13 1.2190(17) . ?
N C9 1.4520(16) . ?
N C1 1.4736(15) . ?
N C11 1.4841(15) . ?
C1 C2 1.5135(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5057(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.3987(18) . ?
C3 C8 1.3951(17) . ?
C4 C5 1.383(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3958(18) . ?
C7 H7A 0.9500 . ?
C8 C9 1.5016(17) . ?
C9 H9A 1.0000 . ?
C10 C11 1.5557(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5202(18) . ?
C11 H11A 1.0000 . ?
C12 C13 1.515(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4951(19) . ?
C14 C15 1.391(2) . ?
C14 C19 1.394(2) . ?
C15 C16 1.389(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
C10 O1 C9 102.91(9) . . ?
C9 N C1 112.09(10) . . ?
C9 N C11 102.91(9) . . ?
C1 N C11 112.80(10) . . ?
N C1 C2 108.56(10) . . ?
N C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 C1 110.99(10) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C8 118.74(12) . . ?
C4 C3 C2 121.65(11) . . ?
C8 C3 C2 119.61(11) . . ?
C5 C4 C3 120.87(13) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.12(13) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C7 C6 C5 119.59(13) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 120.69(13) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
C7 C8 C3 119.97(12) . . ?
C7 C8 C9 118.90(11) . . ?
C3 C8 C9 121.12(11) . . ?
O1 C9 N 106.17(10) . . ?
O1 C9 C8 110.05(10) . . ?
N C9 C8 115.05(10) . . ?
O1 C9 H9A 108.5 . . ?
N C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
O1 C10 C11 105.75(10) . . ?
O1 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
O1 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
N C11 C12 109.39(10) . . ?
N C11 C10 104.48(10) . . ?
C12 C11 C10 113.30(11) . . ?
N C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
C13 C12 C11 112.00(11) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 C14 119.83(13) . . ?
O2 C13 C12 120.77(12) . . ?
C14 C13 C12 119.40(11) . . ?
C15 C14 C19 118.79(13) . . ?
C15 C14 C13 123.12(13) . . ?
C19 C14 C13 118.08(12) . . ?
C14 C15 C16 120.14(16) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C17 C16 C15 119.99(16) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C18 C17 C16 120.68(16) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 119.22(17) . . ?
C17 C18 H18A 120.4 . . ?
C19 C18 H18A 120.4 . . ?
C18 C19 C14 121.16(15) . . ?
C18 C19 H19A 119.4 . . ?
C14 C19 H19A 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N C1 C2 -65.12(13) . . . . ?
C11 N C1 C2 179.27(10) . . . . ?
N C1 C2 C3 55.79(14) . . . . ?
C1 C2 C3 C4 155.99(12) . . . . ?
C1 C2 C3 C8 -23.51(17) . . . . ?
C8 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C5 -178.23(13) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C6 C7 C8 C3 -0.59(19) . . . . ?
C6 C7 C8 C9 179.97(11) . . . . ?
C4 C3 C8 C7 -0.88(18) . . . . ?
C2 C3 C8 C7 178.64(11) . . . . ?
C4 C3 C8 C9 178.55(11) . . . . ?
C2 C3 C8 C9 -1.94(18) . . . . ?
C10 O1 C9 N -43.09(12) . . . . ?
C10 O1 C9 C8 -168.19(10) . . . . ?
C1 N C9 O1 -82.73(11) . . . . ?
C11 N C9 O1 38.74(11) . . . . ?
C1 N C9 C8 39.25(14) . . . . ?
C11 N C9 C8 160.72(10) . . . . ?
C7 C8 C9 O1 -66.15(14) . . . . ?
C3 C8 C9 O1 114.41(12) . . . . ?
C7 C8 C9 N 173.99(10) . . . . ?
C3 C8 C9 N -5.44(16) . . . . ?
C9 O1 C10 C11 28.90(12) . . . . ?
C9 N C11 C12 102.26(11) . . . . ?
C1 N C11 C12 -136.75(11) . . . . ?
C9 N C11 C10 -19.33(12) . . . . ?
C1 N C11 C10 101.65(12) . . . . ?
O1 C10 C11 N -5.98(13) . . . . ?
O1 C10 C11 C12 -124.96(11) . . . . ?
N C11 C12 C13 72.14(13) . . . . ?
C10 C11 C12 C13 -171.75(11) . . . . ?
C11 C12 C13 O2 18.41(18) . . . . ?
C11 C12 C13 C14 -161.43(11) . . . . ?
O2 C13 C14 C15 174.58(14) . . . . ?
C12 C13 C14 C15 -5.58(19) . . . . ?
O2 C13 C14 C19 -6.84(19) . . . . ?
C12 C13 C14 C19 173.00(12) . . . . ?
C19 C14 C15 C16 -0.3(2) . . . . ?
C13 C14 C15 C16 178.23(14) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C15 C14 C19 C18 1.1(2) . . . . ?
C13 C14 C19 C18 -177.55(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_5fb
_database_code_depnum_ccdc_archive 'CCDC 1483928'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H23 N O3'
_chemical_formula_sum            'C21 H23 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         337.40

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

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

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

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

_cell_length_a                   5.6823(4)
_cell_length_b                   7.0109(5)
_cell_length_c                   21.9839(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.665(7)
_cell_angle_gamma                90
_cell_volume                     874.00(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1812
_cell_measurement_theta_min      4.0220
_cell_measurement_theta_max      28.8840
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) 
(compiled Dec  3 2012,18:21:49) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7756
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.905
_diffrn_reflns_theta_max         29.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3753
_reflns_number_gt                3068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.797
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 806 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.3(10)
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3753
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.2032
_refine_ls_wR_factor_ref         0.5222
_refine_ls_wR_factor_gt          0.5003
_refine_ls_goodness_of_fit_ref   1.818
_refine_ls_restrained_S_all      1.817
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4439(19) 0.7175(14) 0.2075(4) 0.025(2) Uani 1 1 d . . . . .
O2 O 0.950(2) 0.6073(19) 0.3658(4) 0.037(3) Uani 1 1 d . . . . .
O3 O 0.709(2) 0.5083(17) 0.6427(5) 0.030(2) Uani 1 1 d . . . . .
N N 0.426(2) 0.4039(17) 0.2391(5) 0.023(2) Uani 1 1 d . . . . .
C1 C 0.140(2) 0.528(2) 0.1580(6) 0.027(3) Uani 1 1 d . . . . .
C2 C -0.023(3) 0.661(2) 0.1346(6) 0.033(3) Uani 1 1 d . . . . .
H2A H -0.0353 0.7766 0.1570 0.040 Uiso 1 1 calc R U . . .
C3 C -0.165(2) 0.643(3) 0.0833(6) 0.032(3) Uani 1 1 d . . . . .
C4 C -0.156(3) 0.469(3) 0.0529(7) 0.041(4) Uani 1 1 d . . . . .
H4A H -0.2592 0.4462 0.0180 0.049 Uiso 1 1 calc R U . . .
C5 C 0.004(4) 0.327(2) 0.0729(6) 0.037(4) Uani 1 1 d . . . . .
H5A H 0.0109 0.2117 0.0505 0.044 Uiso 1 1 calc R U . . .
C6 C 0.155(3) 0.354(2) 0.1263(6) 0.027(3) Uani 1 1 d . . . . .
C7 C 0.326(3) 0.205(2) 0.1501(6) 0.026(3) Uani 1 1 d . . . . .
H7A H 0.2433 0.1104 0.1744 0.031 Uiso 1 1 calc R U . . .
H7B H 0.3917 0.1373 0.1154 0.031 Uiso 1 1 calc R U . . .
C8 C 0.526(3) 0.294(2) 0.1895(6) 0.031(3) Uani 1 1 d . . . . .
H8A H 0.6320 0.1930 0.2069 0.037 Uiso 1 1 calc R U . . .
H8B H 0.6196 0.3794 0.1644 0.037 Uiso 1 1 calc R U . . .
C9 C 0.280(3) 0.5651(19) 0.2158(6) 0.023(3) Uani 1 1 d . . . . .
H9A H 0.1702 0.6036 0.2475 0.027 Uiso 1 1 calc R U . . .
C10 C 0.603(3) 0.709(2) 0.2604(6) 0.026(3) Uani 1 1 d . . . . .
H10A H 0.5437 0.7874 0.2937 0.031 Uiso 1 1 calc R U . . .
H10B H 0.7608 0.7567 0.2511 0.031 Uiso 1 1 calc R U . . .
C11 C 0.614(3) 0.496(2) 0.2786(6) 0.027(3) Uani 1 1 d . . . . .
H11A H 0.7714 0.4414 0.2699 0.032 Uiso 1 1 calc R U . . .
C12 C 0.570(3) 0.467(2) 0.3459(6) 0.027(3) Uani 1 1 d . . . . .
H12A H 0.5459 0.3299 0.3539 0.032 Uiso 1 1 calc R U . . .
H12B H 0.4244 0.5358 0.3553 0.032 Uiso 1 1 calc R U . . .
C13 C 0.777(3) 0.541(2) 0.3876(6) 0.024(3) Uani 1 1 d . . . . .
C14 C 0.756(2) 0.5311(18) 0.4553(5) 0.019(2) Uani 1 1 d . . . . .
C15 C 0.558(2) 0.4600(17) 0.4815(6) 0.017(2) Uani 1 1 d . . . . .
H15A H 0.4282 0.4149 0.4562 0.021 Uiso 1 1 calc R U . . .
C16 C 0.548(2) 0.4543(18) 0.5450(6) 0.020(2) Uani 1 1 d . . . . .
H16A H 0.4121 0.4064 0.5627 0.024 Uiso 1 1 calc R U . . .
C17 C 0.740(3) 0.519(2) 0.5820(6) 0.023(3) Uani 1 1 d . . . . .
C18 C 0.936(2) 0.5964(19) 0.5561(6) 0.019(3) Uani 1 1 d . . . . .
H18A H 1.0640 0.6460 0.5813 0.023 Uiso 1 1 calc R U . . .
C19 C 0.943(2) 0.5999(19) 0.4928(5) 0.021(3) Uani 1 1 d . . . . .
H19A H 1.0782 0.6500 0.4750 0.025 Uiso 1 1 calc R U . . .
C20 C 0.903(3) 0.564(3) 0.6841(7) 0.038(4) Uani 1 1 d . . . . .
H20A H 0.8588 0.5494 0.7262 0.057 Uiso 1 1 calc R U . . .
H20B H 1.0398 0.4825 0.6776 0.057 Uiso 1 1 calc R U . . .
H20C H 0.9442 0.6972 0.6767 0.057 Uiso 1 1 calc R U . . .
C21 C -0.348(3) 0.789(3) 0.0614(7) 0.041(4) Uani 1 1 d . . . . .
H21A H -0.4294 0.7454 0.0234 0.061 Uiso 1 1 calc R U . . .
H21B H -0.4626 0.8063 0.0925 0.061 Uiso 1 1 calc R U . . .
H21C H -0.2698 0.9114 0.0544 0.061 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.428(16) . ?
O1 C9 1.438(17) . ?
O2 C13 1.213(19) . ?
O3 C17 1.360(16) . ?
O3 C20 1.440(18) . ?
N C11 1.481(18) . ?
N C9 1.477(18) . ?
N C8 1.479(18) . ?
C1 C6 1.41(2) . ?
C1 C2 1.39(2) . ?
C1 C9 1.476(17) . ?
C2 C3 1.352(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.39(3) . ?
C3 C21 1.52(2) . ?
C4 C5 1.39(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.423(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.50(2) . ?
C7 C8 1.52(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 1.0000 . ?
C10 C11 1.55(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.529(18) . ?
C11 H11A 1.0000 . ?
C12 C13 1.53(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.503(16) . ?
C14 C15 1.387(17) . ?
C14 C19 1.391(18) . ?
C15 C16 1.399(17) . ?
C15 H15A 0.9500 . ?
C16 C17 1.395(19) . ?
C16 H16A 0.9500 . ?
C17 C18 1.392(18) . ?
C18 C19 1.396(16) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C10 O1 C9 104.4(10) . . ?
C17 O3 C20 117.4(13) . . ?
C11 N C9 104.0(10) . . ?
C11 N C8 111.2(12) . . ?
C9 N C8 112.2(10) . . ?
C6 C1 C2 117.3(12) . . ?
C6 C1 C9 122.3(13) . . ?
C2 C1 C9 120.3(13) . . ?
C3 C2 C1 126.3(15) . . ?
C3 C2 H2A 116.9 . . ?
C1 C2 H2A 116.9 . . ?
C2 C3 C4 116.4(14) . . ?
C2 C3 C21 124.1(15) . . ?
C4 C3 C21 119.2(12) . . ?
C3 C4 C5 121.1(12) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.9(14) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 117.9(14) . . ?
C1 C6 C7 119.2(12) . . ?
C5 C6 C7 122.9(13) . . ?
C8 C7 C6 111.1(12) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N C8 C7 109.0(13) . . ?
N C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
N C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O1 C9 C1 109.8(11) . . ?
O1 C9 N 104.8(11) . . ?
C1 C9 N 115.0(11) . . ?
O1 C9 H9A 109.0 . . ?
C1 C9 H9A 109.0 . . ?
N C9 H9A 109.0 . . ?
O1 C10 C11 105.3(10) . . ?
O1 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
O1 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
N C11 C12 110.7(12) . . ?
N C11 C10 104.6(11) . . ?
C12 C11 C10 111.7(12) . . ?
N C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C11 C12 C13 111.6(12) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O2 C13 C14 121.8(13) . . ?
O2 C13 C12 120.1(12) . . ?
C14 C13 C12 118.1(12) . . ?
C15 C14 C19 119.2(11) . . ?
C15 C14 C13 123.1(12) . . ?
C19 C14 C13 117.7(12) . . ?
C16 C15 C14 120.6(11) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 119.6(12) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
O3 C17 C18 125.6(13) . . ?
O3 C17 C16 114.1(13) . . ?
C18 C17 C16 120.3(12) . . ?
C17 C18 C19 119.3(11) . . ?
C17 C18 H18A 120.4 . . ?
C19 C18 H18A 120.4 . . ?
C18 C19 C14 121.0(12) . . ?
C18 C19 H19A 119.5 . . ?
C14 C19 H19A 119.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         1.886
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.201

####################################################################### 
# 
# 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_ic17273
_database_code_depnum_ccdc_archive 'CCDC 1483929'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br N O2'
_chemical_formula_weight         372.25

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   Pbca

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

_cell_length_a                   10.9980(5)
_cell_length_b                   7.5779(3)
_cell_length_c                   38.7212(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3227.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2145
_cell_measurement_theta_min      4.5990
_cell_measurement_theta_max      74.6100

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    3.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6271
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0492
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         4.62
_diffrn_reflns_theta_max         67.99
_reflns_number_total             2903
_reflns_number_gt                2100
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.1000P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1514
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.006

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 0.85334(5) 0.14353(7) 0.729584(11) 0.0469(2) Uani 1 1 d . . .
O1 O 1.1746(2) -0.1855(4) 0.86262(7) 0.0331(7) Uani 1 1 d . . .
O2 O 1.2339(2) -0.4706(4) 0.96004(7) 0.0376(7) Uani 1 1 d . . .
N1 N 0.9893(3) -0.2840(5) 0.88325(8) 0.0294(7) Uani 1 1 d . . .
C1 C 0.9102(4) 0.0637(6) 0.77339(9) 0.0347(10) Uani 1 1 d . . .
C2 C 1.0007(4) 0.1564(7) 0.79014(12) 0.0435(11) Uani 1 1 d . . .
H2A H 1.0337 0.2610 0.7804 0.052 Uiso 1 1 calc R . .
C3 C 1.0420(4) 0.0930(6) 0.82135(12) 0.0408(10) Uani 1 1 d . . .
H3A H 1.1025 0.1571 0.8336 0.049 Uiso 1 1 calc R . .
C4 C 0.9971(3) -0.0626(5) 0.83532(10) 0.0309(9) Uani 1 1 d . . .
C5 C 1.0508(3) -0.1320(5) 0.86846(10) 0.0283(8) Uani 1 1 d . . .
H5A H 1.0506 -0.0347 0.8859 0.034 Uiso 1 1 calc R . .
C6 C 1.2042(3) -0.2832(6) 0.89329(10) 0.0321(9) Uani 1 1 d . . .
H6A H 1.2405 -0.2047 0.9109 0.039 Uiso 1 1 calc R . .
H6B H 1.2627 -0.3788 0.8880 0.039 Uiso 1 1 calc R . .
C7 C 1.0826(3) -0.3609(5) 0.90633(9) 0.0281(8) Uani 1 1 d . . .
H7A H 1.0836 -0.4920 0.9035 0.034 Uiso 1 1 calc R . .
C8 C 0.9514(5) -0.4087(6) 0.85624(11) 0.0460(12) Uani 1 1 d . . .
H8A H 0.9160 -0.5154 0.8670 0.055 Uiso 1 1 calc R . .
H8B H 1.0231 -0.4453 0.8425 0.055 Uiso 1 1 calc R . .
C9 C 0.8591(5) -0.3242(7) 0.83293(14) 0.0565(15) Uani 1 1 d . . .
H9A H 0.8393 -0.4059 0.8138 0.068 Uiso 1 1 calc R . .
H9B H 0.7835 -0.3017 0.8461 0.068 Uiso 1 1 calc R . .
C10 C 0.9057(4) -0.1530(6) 0.81825(10) 0.0366(10) Uani 1 1 d . . .
C11 C 0.8624(4) -0.0880(7) 0.78681(11) 0.0373(10) Uani 1 1 d . . .
H11A H 0.8000 -0.1491 0.7748 0.045 Uiso 1 1 calc R . .
C12 C 1.0549(3) -0.3151(5) 0.94401(10) 0.0284(8) Uani 1 1 d . . .
H12A H 1.0494 -0.1852 0.9462 0.034 Uiso 1 1 calc R . .
H12B H 0.9746 -0.3649 0.9502 0.034 Uiso 1 1 calc R . .
C13 C 1.1477(3) -0.3820(5) 0.96920(10) 0.0289(8) Uani 1 1 d . . .
C14 C 1.1323(3) -0.3339(5) 1.00666(10) 0.0264(8) Uani 1 1 d . . .
C15 C 1.2247(3) -0.3736(5) 1.02999(10) 0.0295(8) Uani 1 1 d . . .
H15A H 1.2946 -0.4357 1.0223 0.035 Uiso 1 1 calc R . .
C16 C 1.2156(4) -0.3235(6) 1.06425(10) 0.0356(10) Uani 1 1 d . . .
H16A H 1.2795 -0.3497 1.0799 0.043 Uiso 1 1 calc R . .
C17 C 1.1125(4) -0.2349(5) 1.07558(11) 0.0328(9) Uani 1 1 d . . .
H17A H 1.1068 -0.1985 1.0990 0.039 Uiso 1 1 calc R . .
C18 C 1.0188(4) -0.1994(5) 1.05320(11) 0.0323(9) Uani 1 1 d . . .
H18A H 0.9473 -0.1423 1.0613 0.039 Uiso 1 1 calc R . .
C19 C 1.0288(3) -0.2471(5) 1.01865(10) 0.0295(9) Uani 1 1 d . . .
H19A H 0.9646 -0.2205 1.0031 0.035 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 C1 1.906(4) . ?
O1 C5 1.438(5) . ?
O1 C6 1.437(5) . ?
O2 C13 1.214(5) . ?
N1 C5 1.454(5) . ?
N1 C8 1.470(5) . ?
N1 C7 1.480(5) . ?
C1 C11 1.367(7) . ?
C1 C2 1.381(6) . ?
C2 C3 1.378(6) . ?
C3 C4 1.388(6) . ?
C4 C10 1.385(6) . ?
C4 C5 1.507(5) . ?
C6 C7 1.546(5) . ?
C7 C12 1.530(5) . ?
C8 C9 1.502(7) . ?
C9 C10 1.506(6) . ?
C10 C11 1.397(6) . ?
C12 C13 1.500(5) . ?
C13 C14 1.505(6) . ?
C14 C15 1.392(5) . ?
C14 C19 1.395(5) . ?
C15 C16 1.383(6) . ?
C16 C17 1.388(6) . ?
C17 C18 1.374(6) . ?
C18 C19 1.390(6) . ?

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 O1 C6 103.3(3) . . ?
C5 N1 C8 111.1(3) . . ?
C5 N1 C7 103.1(3) . . ?
C8 N1 C7 111.9(3) . . ?
C11 C1 C2 121.8(4) . . ?
C11 C1 Br1 118.6(3) . . ?
C2 C1 Br1 119.5(4) . . ?
C3 C2 C1 118.2(4) . . ?
C2 C3 C4 121.4(4) . . ?
C3 C4 C10 119.5(4) . . ?
C3 C4 C5 119.3(4) . . ?
C10 C4 C5 121.2(4) . . ?
O1 C5 N1 106.2(3) . . ?
O1 C5 C4 109.6(3) . . ?
N1 C5 C4 115.4(3) . . ?
O1 C6 C7 105.7(3) . . ?
N1 C7 C12 110.4(3) . . ?
N1 C7 C6 104.7(3) . . ?
C12 C7 C6 113.4(3) . . ?
N1 C8 C9 110.2(4) . . ?
C10 C9 C8 111.4(4) . . ?
C11 C10 C4 119.3(4) . . ?
C11 C10 C9 121.1(4) . . ?
C4 C10 C9 119.5(4) . . ?
C1 C11 C10 119.8(4) . . ?
C13 C12 C7 114.1(3) . . ?
O2 C13 C12 121.9(4) . . ?
O2 C13 C14 120.2(4) . . ?
C12 C13 C14 117.9(3) . . ?
C15 C14 C19 118.8(4) . . ?
C15 C14 C13 119.4(3) . . ?
C19 C14 C13 121.8(3) . . ?
C14 C15 C16 120.7(4) . . ?
C17 C16 C15 119.6(4) . . ?
C18 C17 C16 120.5(4) . . ?
C17 C18 C19 119.8(4) . . ?
C18 C19 C14 120.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        67.99
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.084
