# Electronic Supplementary Material (ESI) for ChemComm.
# 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_276
_database_code_depnum_ccdc_archive 'CCDC 1440804'
_audit_update_record             
;
2015-12-05 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N O3 '
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6614(2)
_cell_length_b                   9.0050(2)
_cell_length_c                   18.1004(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.9684(13)
_cell_angle_gamma                90
_cell_volume                     1573.82(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6003
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.04

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12074
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         27.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3472
_reflns_number_gt                2667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.3270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0107(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.5859(2) 0.8233(3) 0.56777(9) 0.0847(6) Uani 1 1 d . . . . .
H1A H 0.5062 0.7816 0.5424 0.127 Uiso 1 1 calc R U . . .
H1B H 0.6685 0.7853 0.5466 0.127 Uiso 1 1 calc R U . . .
H1C H 0.5839 0.9295 0.5630 0.127 Uiso 1 1 calc R U . . .
C2 C 0.58447(17) 0.78199(18) 0.64826(8) 0.0557(4) Uani 1 1 d . . . . .
C3 C 0.48745(18) 0.84299(18) 0.69306(8) 0.0565(4) Uani 1 1 d . . . . .
H3 H 0.4254 0.9128 0.6736 0.068 Uiso 1 1 calc R U . . .
C4 C 0.48036(16) 0.80275(17) 0.76638(8) 0.0503(4) Uani 1 1 d . . . . .
H4 H 0.4144 0.8466 0.7956 0.060 Uiso 1 1 calc R U . . .
C5 C 0.57067(13) 0.69728(15) 0.79719(7) 0.0402(3) Uani 1 1 d . . . . .
C6 C 0.66992(15) 0.63693(17) 0.75241(8) 0.0523(4) Uani 1 1 d . . . . .
H6 H 0.7322 0.5670 0.7716 0.063 Uiso 1 1 calc R U . . .
C7 C 0.67668(17) 0.6804(2) 0.67912(9) 0.0622(4) Uani 1 1 d . . . . .
H7 H 0.7448 0.6402 0.6501 0.075 Uiso 1 1 calc R U . . .
C8 C 0.55964(13) 0.64308(14) 0.87439(7) 0.0402(3) Uani 1 1 d . . . . .
C9 C 0.44189(13) 0.70396(14) 0.92048(7) 0.0397(3) Uani 1 1 d . . . . .
H9 H 0.4265 0.8083 0.9071 0.048 Uiso 1 1 calc R U . . .
C10 C 0.31047(14) 0.61678(17) 0.90044(8) 0.0485(3) Uani 1 1 d . . . . .
H10A H 0.3191 0.5175 0.9193 0.073 Uiso 1 1 calc R U . . .
H10B H 0.2972 0.6136 0.8477 0.073 Uiso 1 1 calc R U . . .
H10C H 0.2324 0.6644 0.9217 0.073 Uiso 1 1 calc R U . . .
C11 C 0.56861(14) 0.78093(14) 1.03513(7) 0.0395(3) Uani 1 1 d . . . . .
C12 C 0.58238(15) 0.77427(15) 1.11262(7) 0.0433(3) Uani 1 1 d . . . . .
H12 H 0.5254 0.7113 1.1387 0.052 Uiso 1 1 calc R U . . .
C13 C 0.67907(15) 0.85968(15) 1.15024(7) 0.0442(3) Uani 1 1 d . . . . .
H13 H 0.6856 0.8546 1.2016 0.053 Uiso 1 1 calc R U . . .
C14 C 0.76763(14) 0.95371(14) 1.11316(7) 0.0420(3) Uani 1 1 d . . . . .
C15 C 0.75518(15) 0.95959(15) 1.03645(8) 0.0468(3) Uani 1 1 d . . . . .
H15 H 0.8144 1.0205 1.0106 0.056 Uiso 1 1 calc R U . . .
C16 C 0.65664(16) 0.87672(15) 0.99795(7) 0.0469(3) Uani 1 1 d . . . . .
H16 H 0.6486 0.8846 0.9468 0.056 Uiso 1 1 calc R U . . .
C17 C 0.86656(15) 1.04664(15) 1.15626(8) 0.0470(3) Uani 1 1 d . . . . .
C18 C 1.05518(19) 1.2124(2) 1.15059(12) 0.0760(5) Uani 1 1 d . . . . .
H18A H 1.0052 1.2858 1.1774 0.114 Uiso 1 1 calc R U . . .
H18B H 1.1113 1.2606 1.1150 0.114 Uiso 1 1 calc R U . . .
H18C H 1.1134 1.1565 1.1844 0.114 Uiso 1 1 calc R U . . .
N1 N 0.47061(13) 0.69554(13) 0.99901(6) 0.0463(3) Uani 1 1 d . . . . .
O1 O 0.63845(11) 0.54955(12) 0.90004(6) 0.0577(3) Uani 1 1 d . . . . .
O2 O 0.86532(12) 1.06470(13) 1.22229(6) 0.0653(3) Uani 1 1 d . . . . .
O3 O 0.95885(11) 1.11413(12) 1.11318(6) 0.0601(3) Uani 1 1 d . . . . .
H1N H 0.4304(16) 0.6245(18) 1.0247(9) 0.051(4) Uiso 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
C1 C2 1.504(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.375(2) . ?
C2 C7 1.382(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3932(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(2) . ?
C5 C8 1.4875(18) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.2167(15) . ?
C8 C9 1.5348(19) . ?
C9 N1 1.4410(16) . ?
C9 C10 1.5258(18) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N1 1.3684(17) . ?
C11 C16 1.3999(19) . ?
C11 C12 1.4056(17) . ?
C12 C13 1.3727(19) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.3907(19) . ?
C14 C17 1.4735(19) . ?
C15 C16 1.3796(19) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.2067(17) . ?
C17 O3 1.3492(19) . ?
C18 O3 1.4370(18) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1N 0.888(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.98(14) . . ?
C3 C2 C1 120.10(17) . . ?
C7 C2 C1 121.90(17) . . ?
C2 C3 C4 121.32(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 120.86(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 117.98(13) . . ?
C6 C5 C8 119.57(13) . . ?
C4 C5 C8 122.39(12) . . ?
C7 C6 C5 120.30(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C2 C7 C6 121.52(15) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
O1 C8 C5 121.43(13) . . ?
O1 C8 C9 120.38(12) . . ?
C5 C8 C9 118.15(11) . . ?
N1 C9 C10 109.75(11) . . ?
N1 C9 C8 113.33(11) . . ?
C10 C9 C8 108.26(10) . . ?
N1 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C8 C9 H9 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C16 122.57(12) . . ?
N1 C11 C12 119.54(12) . . ?
C16 C11 C12 117.89(12) . . ?
C13 C12 C11 120.70(13) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.38(12) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 118.09(12) . . ?
C15 C14 C17 122.63(13) . . ?
C13 C14 C17 119.24(12) . . ?
C16 C15 C14 121.21(13) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 120.71(12) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O2 C17 O3 122.75(13) . . ?
O2 C17 C14 124.93(15) . . ?
O3 C17 C14 112.30(12) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N1 C9 123.26(11) . . ?
C11 N1 H1N 117.6(10) . . ?
C9 N1 H1N 118.7(10) . . ?
C17 O3 C18 115.80(14) . . ?

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
C7 C2 C3 C4 -1.0(2) . . . . ?
C1 C2 C3 C4 177.46(15) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C3 C4 C5 C8 -175.47(13) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C8 C5 C6 C7 176.48(13) . . . . ?
C3 C2 C7 C6 1.9(2) . . . . ?
C1 C2 C7 C6 -176.49(15) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C6 C5 C8 O1 2.08(19) . . . . ?
C4 C5 C8 O1 179.08(13) . . . . ?
C6 C5 C8 C9 -175.56(12) . . . . ?
C4 C5 C8 C9 1.44(18) . . . . ?
O1 C8 C9 N1 26.34(17) . . . . ?
C5 C8 C9 N1 -155.99(11) . . . . ?
O1 C8 C9 C10 -95.66(14) . . . . ?
C5 C8 C9 C10 82.01(14) . . . . ?
N1 C11 C12 C13 -179.46(12) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C12 C13 C14 C17 178.05(12) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C17 C14 C15 C16 -176.63(13) . . . . ?
C14 C15 C16 C11 -1.8(2) . . . . ?
N1 C11 C16 C15 -179.23(13) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
C15 C14 C17 O2 166.60(14) . . . . ?
C13 C14 C17 O2 -11.0(2) . . . . ?
C15 C14 C17 O3 -11.81(18) . . . . ?
C13 C14 C17 O3 170.56(12) . . . . ?
C16 C11 N1 C9 -4.7(2) . . . . ?
C12 C11 N1 C9 174.94(12) . . . . ?
C10 C9 N1 C11 -169.46(12) . . . . ?
C8 C9 N1 C11 69.37(16) . . . . ?
O2 C17 O3 C18 -1.2(2) . . . . ?
C14 C17 O3 C18 177.23(12) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_327
_database_code_depnum_ccdc_archive 'CCDC 1440805'
_audit_update_record             
;
2015-12-05 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N2 S'
_chemical_formula_sum            'C17 H16 N2 S'
_chemical_formula_weight         280.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0979(2)
_cell_length_b                   9.8360(2)
_cell_length_c                   17.0069(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.3206(11)
_cell_angle_gamma                90
_cell_volume                     1486.84(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5165
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.17

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11081
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2614
_reflns_number_gt                2237
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2614
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.7979(3) 0.6859(2) 0.25961(11) 0.0607(6) Uani 1 1 d . . . . .
H1 H 0.7432 0.7381 0.2179 0.073 Uiso 1 1 calc R U . . .
C2 C 0.8363(3) 0.7383(2) 0.33674(12) 0.0657(6) Uani 1 1 d . . . . .
H2 H 0.8083 0.8265 0.3467 0.079 Uiso 1 1 calc R U . . .
C3 C 0.9151(2) 0.6615(2) 0.39811(11) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.9412 0.6973 0.4498 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9556(2) 0.5313(2) 0.38338(11) 0.0597(5) Uani 1 1 d . . . . .
H4 H 1.0084 0.4785 0.4254 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9185(2) 0.4780(2) 0.30634(10) 0.0520(5) Uani 1 1 d . . . . .
H5 H 0.9460 0.3897 0.2963 0.062 Uiso 1 1 calc R U . . .
C6 C 0.84085(19) 0.55696(17) 0.24517(9) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.88977(19) 0.51602(17) 0.10934(9) 0.0413(4) Uani 1 1 d . . . . .
C8 C 0.69151(19) 0.37899(17) 0.06050(9) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.6792(2) 0.41812(18) 0.13527(10) 0.0458(4) Uani 1 1 d . . . . .
C10 C 0.5659(3) 0.3867(3) 0.18374(13) 0.0737(7) Uani 1 1 d . . . . .
H10A H 0.5084 0.4669 0.1886 0.111 Uiso 1 1 calc R U . . .
H10B H 0.6160 0.3565 0.2363 0.111 Uiso 1 1 calc R U . . .
H10C H 0.4999 0.3165 0.1576 0.111 Uiso 1 1 calc R U . . .
C11 C 0.60052(19) 0.28483(17) 0.00289(9) 0.0408(4) Uani 1 1 d . . . . .
C12 C 0.6695(2) 0.19394(18) -0.04047(10) 0.0455(4) Uani 1 1 d . . . . .
H12 H 0.7733 0.1970 -0.0353 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5863(2) 0.09954(18) -0.09100(10) 0.0466(4) Uani 1 1 d . . . . .
H13 H 0.6353 0.0399 -0.1192 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4321(2) 0.09128(18) -0.10079(9) 0.0438(4) Uani 1 1 d . . . . .
C15 C 0.3632(2) 0.18303(19) -0.05826(11) 0.0498(4) Uani 1 1 d . . . . .
H15 H 0.2593 0.1801 -0.0639 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4452(2) 0.27852(19) -0.00774(10) 0.0482(4) Uani 1 1 d . . . . .
H16 H 0.3957 0.3394 0.0195 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3430(2) -0.0136(2) -0.15544(12) 0.0584(5) Uani 1 1 d . . . . .
H17A H 0.4084 -0.0614 -0.1834 0.088 Uiso 1 1 calc R U . . .
H17B H 0.2648 0.0305 -0.1938 0.088 Uiso 1 1 calc R U . . .
H17C H 0.2991 -0.0767 -0.1240 0.088 Uiso 1 1 calc R U . . .
N1 N 0.80265(16) 0.50187(14) 0.16480(8) 0.0429(3) Uani 1 1 d . . . . .
N2 N 0.82084(17) 0.44004(15) 0.04631(8) 0.0422(3) Uani 1 1 d . . . . .
S1 S 1.04698(6) 0.61045(5) 0.11818(3) 0.05334(17) Uani 1 1 d . . . . .
H2N H 0.857(2) 0.433(2) 0.0038(13) 0.059(6) Uiso 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
C1 C6 1.365(3) . ?
C1 C2 1.383(3) . ?
C2 C3 1.361(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.368(2) . ?
C6 N1 1.4421(19) . ?
C7 N2 1.347(2) . ?
C7 N1 1.362(2) . ?
C7 S1 1.6850(18) . ?
C8 C9 1.356(2) . ?
C8 N2 1.387(2) . ?
C8 C11 1.469(2) . ?
C9 N1 1.397(2) . ?
C9 C10 1.483(3) . ?
C11 C16 1.387(2) . ?
C11 C12 1.391(2) . ?
C12 C13 1.377(2) . ?
C13 C14 1.379(2) . ?
C14 C15 1.387(3) . ?
C14 C17 1.505(2) . ?
C15 C16 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.52(18) . . ?
C3 C2 C1 120.38(19) . . ?
C2 C3 C4 119.74(17) . . ?
C3 C4 C5 120.40(18) . . ?
C6 C5 C4 119.15(18) . . ?
C1 C6 C5 120.79(16) . . ?
C1 C6 N1 119.96(15) . . ?
C5 C6 N1 119.25(15) . . ?
N2 C7 N1 104.68(15) . . ?
N2 C7 S1 128.25(13) . . ?
N1 C7 S1 127.06(13) . . ?
C9 C8 N2 106.44(15) . . ?
C9 C8 C11 131.09(16) . . ?
N2 C8 C11 122.36(14) . . ?
C8 C9 N1 106.48(15) . . ?
C8 C9 C10 131.93(17) . . ?
N1 C9 C10 121.58(15) . . ?
C16 C11 C12 117.68(16) . . ?
C16 C11 C8 121.91(15) . . ?
C12 C11 C8 120.34(15) . . ?
C13 C12 C11 120.93(17) . . ?
C12 C13 C14 121.65(16) . . ?
C13 C14 C15 117.40(16) . . ?
C13 C14 C17 121.00(17) . . ?
C15 C14 C17 121.61(17) . . ?
C16 C15 C14 121.53(17) . . ?
C15 C16 C11 120.80(17) . . ?
C7 N1 C9 110.68(13) . . ?
C7 N1 C6 124.03(14) . . ?
C9 N1 C6 125.10(13) . . ?
C7 N2 C8 111.71(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C6 N1 -179.37(19) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 N1 179.71(17) . . . . ?
N2 C8 C9 N1 -0.29(19) . . . . ?
C11 C8 C9 N1 175.72(16) . . . . ?
N2 C8 C9 C10 180.0(2) . . . . ?
C11 C8 C9 C10 -4.0(4) . . . . ?
C9 C8 C11 C16 38.9(3) . . . . ?
N2 C8 C11 C16 -145.66(17) . . . . ?
C9 C8 C11 C12 -138.2(2) . . . . ?
N2 C8 C11 C12 37.3(2) . . . . ?
C16 C11 C12 C13 -1.1(2) . . . . ?
C8 C11 C12 C13 176.01(15) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C17 -179.23(16) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C17 C14 C15 C16 179.54(16) . . . . ?
C14 C15 C16 C11 -0.7(3) . . . . ?
C12 C11 C16 C15 1.4(3) . . . . ?
C8 C11 C16 C15 -175.65(16) . . . . ?
N2 C7 N1 C9 -0.62(19) . . . . ?
S1 C7 N1 C9 178.42(13) . . . . ?
N2 C7 N1 C6 174.55(14) . . . . ?
S1 C7 N1 C6 -6.4(2) . . . . ?
C8 C9 N1 C7 0.6(2) . . . . ?
C10 C9 N1 C7 -179.65(19) . . . . ?
C8 C9 N1 C6 -174.52(15) . . . . ?
C10 C9 N1 C6 5.2(3) . . . . ?
C1 C6 N1 C7 88.5(2) . . . . ?
C5 C6 N1 C7 -92.3(2) . . . . ?
C1 C6 N1 C9 -97.0(2) . . . . ?
C5 C6 N1 C9 82.2(2) . . . . ?
N1 C7 N2 C8 0.43(19) . . . . ?
S1 C7 N2 C8 -178.59(13) . . . . ?
C9 C8 N2 C7 -0.1(2) . . . . ?
C11 C8 N2 C7 -176.53(15) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_289
_database_code_depnum_ccdc_archive 'CCDC 1440806'
_audit_update_record             
;
2015-12-05 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br N O'
_chemical_formula_sum            'C16 H16 Br N O'
_chemical_formula_weight         318.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4037(4)
_cell_length_b                   9.4552(3)
_cell_length_c                   13.0281(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.5942(17)
_cell_angle_gamma                90
_cell_volume                     1501.88(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3625
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.21

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    2.729
_shelx_estimated_absorpt_T_min   0.448
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  0.549
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10970
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2651
_reflns_number_gt                1856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+1.5947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2651
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_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
Br1 Br 0.55239(4) 1.10809(5) 1.25264(5) 0.0955(2) Uani 1 1 d . . . . .
C1 C 0.1687(3) 0.7631(4) 0.7316(3) 0.0561(9) Uani 1 1 d . . . . .
H1 H 0.1829 0.6867 0.7770 0.067 Uiso 1 1 calc R U . . .
C2 C 0.1906(3) 0.7530(4) 0.6318(3) 0.0680(11) Uani 1 1 d . . . . .
H2 H 0.2204 0.6698 0.6112 0.082 Uiso 1 1 calc R U . . .
C3 C 0.1693(3) 0.8633(5) 0.5619(3) 0.0635(10) Uani 1 1 d . . . . .
C4 C 0.1250(3) 0.9855(4) 0.5954(3) 0.0682(10) Uani 1 1 d . . . . .
H4 H 0.1094 1.0613 0.5496 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1038(3) 0.9970(4) 0.6942(3) 0.0581(9) Uani 1 1 d . . . . .
H5 H 0.0742 1.0805 0.7148 0.070 Uiso 1 1 calc R U . . .
C6 C 0.1257(2) 0.8862(3) 0.7642(3) 0.0461(8) Uani 1 1 d . . . . .
C7 C 0.1034(2) 0.9076(3) 0.8716(3) 0.0483(8) Uani 1 1 d . . . . .
C8 C 0.1036(3) 0.7825(4) 0.9456(3) 0.0542(8) Uani 1 1 d . . . . .
H8 H 0.1583 0.7133 0.9326 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2245(3) 0.8910(4) 1.0964(3) 0.0515(8) Uani 1 1 d . . . . .
C10 C 0.3196(3) 0.8746(4) 1.0554(3) 0.0659(10) Uani 1 1 d . . . . .
H10 H 0.3182 0.8207 0.9954 0.079 Uiso 1 1 calc R U . . .
C11 C 0.4164(3) 0.9379(4) 1.1034(4) 0.0720(11) Uani 1 1 d . . . . .
H11 H 0.4801 0.9243 1.0765 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4188(3) 1.0200(4) 1.1897(3) 0.0630(10) Uani 1 1 d . . . . .
C13 C 0.3265(3) 1.0387(4) 1.2311(3) 0.0621(9) Uani 1 1 d . . . . .
H13 H 0.3286 1.0946 1.2902 0.074 Uiso 1 1 calc R U . . .
C14 C 0.2304(3) 0.9744(4) 1.1849(3) 0.0571(9) Uani 1 1 d . . . . .
H14 H 0.1678 0.9870 1.2137 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1936(4) 0.8524(6) 0.4532(3) 0.1027(16) Uani 1 1 d . . . . .
H15A H 0.1262 0.8575 0.4034 0.154 Uiso 1 1 calc R U . . .
H15B H 0.2292 0.7640 0.4455 0.154 Uiso 1 1 calc R U . . .
H15C H 0.2407 0.9289 0.4413 0.154 Uiso 1 1 calc R U . . .
C16 C -0.0102(3) 0.7150(4) 0.9215(3) 0.0742(11) Uani 1 1 d . . . . .
H16A H -0.0117 0.6332 0.9648 0.111 Uiso 1 1 calc R U . . .
H16B H -0.0263 0.6875 0.8494 0.111 Uiso 1 1 calc R U . . .
H16C H -0.0640 0.7820 0.9352 0.111 Uiso 1 1 calc R U . . .
N1 N 0.1271(3) 0.8237(3) 1.0541(2) 0.0583(8) Uani 1 1 d . . . . .
O1 O 0.0810(2) 1.0244(2) 0.9002(2) 0.0655(7) Uani 1 1 d . . . . .
H1N H 0.076(3) 0.860(3) 1.070(2) 0.039(10) Uiso 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
Br1 C12 1.901(4) . ?
C1 C2 1.380(5) . ?
C1 C6 1.380(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(5) . ?
C3 C15 1.504(6) . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(5) . ?
C7 O1 1.214(4) . ?
C7 C8 1.525(5) . ?
C8 N1 1.442(4) . ?
C8 C16 1.528(5) . ?
C8 H8 0.9800 . ?
C9 C14 1.388(5) . ?
C9 N1 1.388(4) . ?
C9 C10 1.390(5) . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(5) . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1N 0.79(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.2(4) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 117.6(3) . . ?
C2 C3 C15 121.5(4) . . ?
C4 C3 C15 120.9(4) . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 123.6(3) . . ?
C5 C6 C7 118.0(3) . . ?
O1 C7 C6 120.3(3) . . ?
O1 C7 C8 119.0(3) . . ?
C6 C7 C8 120.6(3) . . ?
N1 C8 C7 112.7(3) . . ?
N1 C8 C16 109.1(3) . . ?
C7 C8 C16 107.5(3) . . ?
N1 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C16 C8 H8 109.2 . . ?
C14 C9 N1 120.0(3) . . ?
C14 C9 C10 117.7(3) . . ?
N1 C9 C10 122.3(3) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 Br1 119.4(3) . . ?
C13 C12 Br1 120.1(3) . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 N1 C8 121.1(3) . . ?
C9 N1 H1N 113(2) . . ?
C8 N1 H1N 110(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C15 179.8(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C15 C3 C4 C5 -179.3(4) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
C2 C1 C6 C7 -177.8(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C1 C6 C7 O1 169.1(3) . . . . ?
C5 C6 C7 O1 -9.7(5) . . . . ?
C1 C6 C7 C8 -13.5(5) . . . . ?
C5 C6 C7 C8 167.6(3) . . . . ?
O1 C7 C8 N1 -27.3(4) . . . . ?
C6 C7 C8 N1 155.3(3) . . . . ?
O1 C7 C8 C16 92.9(4) . . . . ?
C6 C7 C8 C16 -84.5(4) . . . . ?
C14 C9 C10 C11 1.1(5) . . . . ?
N1 C9 C10 C11 -176.6(3) . . . . ?
C9 C10 C11 C12 -1.7(6) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C10 C11 C12 Br1 -179.0(3) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
Br1 C12 C13 C14 -180.0(3) . . . . ?
C12 C13 C14 C9 -0.4(5) . . . . ?
N1 C9 C14 C13 177.7(3) . . . . ?
C10 C9 C14 C13 -0.1(5) . . . . ?
C14 C9 N1 C8 156.3(3) . . . . ?
C10 C9 N1 C8 -26.0(5) . . . . ?
C7 C8 N1 C9 -59.2(4) . . . . ?
C16 C8 N1 C9 -178.4(3) . . . . ?

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_131
_database_code_depnum_ccdc_archive 'CCDC 1440807'
_audit_update_record             
;
2015-12-05 deposited with the CCDC.
2016-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9551(4)
_cell_length_b                   9.4163(6)
_cell_length_c                   14.8711(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.037(2)
_cell_angle_gamma                90
_cell_volume                     1249.15(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2967
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.26

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9305
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.560
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2188
_reflns_number_gt                1498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0554P)²+0.0318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2188
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_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
C1 C 0.27417(18) 0.03509(17) 0.53655(11) 0.0646(5) Uani 1 1 d . . . . .
H1 H 0.3551 0.0250 0.5019 0.078 Uiso 1 1 calc R U . . .
C2 C 0.2008(2) -0.08353(19) 0.56376(13) 0.0823(6) Uani 1 1 d . . . . .
H2 H 0.2318 -0.1733 0.5472 0.099 Uiso 1 1 calc R U . . .
C3 C 0.0817(2) -0.0698(2) 0.61538(12) 0.0791(6) Uani 1 1 d . . . . .
H3 H 0.0327 -0.1504 0.6339 0.095 Uiso 1 1 calc R U . . .
C4 C 0.03510(19) 0.0612(2) 0.63962(12) 0.0702(5) Uani 1 1 d . . . . .
H4 H -0.0455 0.0700 0.6746 0.084 Uiso 1 1 calc R U . . .
C5 C 0.10741(16) 0.18105(16) 0.61230(10) 0.0572(4) Uani 1 1 d . . . . .
H5 H 0.0748 0.2703 0.6288 0.069 Uiso 1 1 calc R U . . .
C6 C 0.22846(14) 0.16960(15) 0.56030(9) 0.0473(4) Uani 1 1 d . . . . .
C7 C 0.30965(14) 0.29510(15) 0.52863(9) 0.0490(4) Uani 1 1 d . . . . .
C8 C 0.25644(15) 0.44443(15) 0.54934(9) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.1477 0.4419 0.5527 0.060 Uiso 1 1 calc R U . . .
C9 C 0.22114(14) 0.54937(15) 0.39600(10) 0.0489(4) Uani 1 1 d . . . . .
C10 C 0.26217(16) 0.65257(17) 0.33543(11) 0.0643(5) Uani 1 1 d . . . . .
H10 H 0.3374 0.7172 0.3535 0.077 Uiso 1 1 calc R U . . .
C11 C 0.1930(2) 0.6599(2) 0.24964(13) 0.0809(6) Uani 1 1 d . . . . .
H11 H 0.2222 0.7293 0.2103 0.097 Uiso 1 1 calc R U . . .
C12 C 0.0813(2) 0.5665(2) 0.22085(12) 0.0825(6) Uani 1 1 d . . . . .
H12 H 0.0346 0.5722 0.1626 0.099 Uiso 1 1 calc R U . . .
C13 C 0.03975(18) 0.46456(19) 0.27958(11) 0.0685(5) Uani 1 1 d . . . . .
H13 H -0.0358 0.4006 0.2608 0.082 Uiso 1 1 calc R U . . .
C14 C 0.10866(16) 0.45538(16) 0.36652(10) 0.0559(4) Uani 1 1 d . . . . .
H14 H 0.0790 0.3854 0.4054 0.067 Uiso 1 1 calc R U . . .
C15 C 0.33025(18) 0.48861(18) 0.64115(10) 0.0662(5) Uani 1 1 d . . . . .
H15A H 0.4369 0.4936 0.6386 0.099 Uiso 1 1 calc R U . . .
H15B H 0.3074 0.4201 0.6857 0.099 Uiso 1 1 calc R U . . .
H15C H 0.2931 0.5800 0.6570 0.099 Uiso 1 1 calc R U . . .
N1 N 0.28951(15) 0.54810(14) 0.48301(9) 0.0581(4) Uani 1 1 d . . . . .
O1 O 0.42138(11) 0.27970(12) 0.48838(8) 0.0727(4) Uani 1 1 d . . . . .
H1N H 0.3741(17) 0.5943(17) 0.4899(9) 0.060(5) Uiso 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
C1 C2 1.375(2) . ?
C1 C6 1.386(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3899(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(2) . ?
C7 O1 1.2188(16) . ?
C7 C8 1.5248(19) . ?
C8 N1 1.4370(18) . ?
C8 C15 1.5217(19) . ?
C8 H8 0.9800 . ?
C9 N1 1.3821(18) . ?
C9 C14 1.383(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.370(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1N 0.871(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.51(17) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.20(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.26(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.05(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.63(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.35(14) . . ?
C1 C6 C7 118.84(14) . . ?
C5 C6 C7 122.81(13) . . ?
O1 C7 C6 120.44(13) . . ?
O1 C7 C8 119.57(13) . . ?
C6 C7 C8 119.95(12) . . ?
N1 C8 C15 109.31(12) . . ?
N1 C8 C7 113.64(11) . . ?
C15 C8 C7 108.33(12) . . ?
N1 C8 H8 108.5 . . ?
C15 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
N1 C9 C14 122.80(14) . . ?
N1 C9 C10 119.34(13) . . ?
C14 C9 C10 117.82(14) . . ?
C11 C10 C9 120.83(15) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.08(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 118.77(16) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 120.96(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 120.54(15) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C8 123.19(12) . . ?
C9 N1 H1N 114.5(10) . . ?
C8 N1 H1N 119.2(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C1 C6 C7 -179.29(13) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 179.61(13) . . . . ?
C1 C6 C7 O1 -5.5(2) . . . . ?
C5 C6 C7 O1 175.02(12) . . . . ?
C1 C6 C7 C8 176.63(12) . . . . ?
C5 C6 C7 C8 -2.83(19) . . . . ?
O1 C7 C8 N1 31.18(18) . . . . ?
C6 C7 C8 N1 -150.95(12) . . . . ?
O1 C7 C8 C15 -90.50(15) . . . . ?
C6 C7 C8 C15 87.36(14) . . . . ?
N1 C9 C10 C11 -177.74(14) . . . . ?
C14 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
N1 C9 C14 C13 177.52(13) . . . . ?
C10 C9 C14 C13 -0.1(2) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C14 C9 N1 C8 3.6(2) . . . . ?
C10 C9 N1 C8 -178.82(13) . . . . ?
C15 C8 N1 C9 -170.28(13) . . . . ?
C7 C8 N1 C9 68.58(17) . . . . ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031

