# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_8b
_database_code_depnum_ccdc_archive 'CCDC 1450298'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;
#1996GuillotICMMO
#Rodolphe BEAU et Guillaume VINCENT msmt1 RB 636 

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H19 N O2'
_chemical_formula_sum            'C18 H19 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         281.34

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, 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                   9.5809(4)
_cell_length_b                   13.6588(6)
_cell_length_c                   22.8484(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2990.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9781
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      33.42
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47102
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.783
_diffrn_reflns_theta_max         33.440
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5808
_reflns_number_gt                4969
_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    ?
_computing_publication_material  ?
_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)+(0.0726P)²+0.8432P] 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_number_reflns         5808
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.015
_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 0.20342(8) 0.90314(5) 0.34200(3) 0.02478(15) Uani 1 1 d . . . . .
O2 O 0.49689(8) 1.23775(5) 0.46427(3) 0.02384(15) Uani 1 1 d . . . . .
N1 N 0.48054(7) 1.08324(5) 0.42865(3) 0.01505(13) Uani 1 1 d . . . . .
C6 C 0.63693(9) 0.95634(6) 0.42091(3) 0.01664(15) Uani 1 1 d . . . . .
C8 C 0.40148(9) 1.00312(6) 0.40027(3) 0.01604(14) Uani 1 1 d . . . . .
H8 H 0.3115 0.9940 0.4199 0.019 Uiso 1 1 calc R U . . .
C1 C 0.62257(8) 1.05597(6) 0.43412(3) 0.01462(14) Uani 1 1 d . . . . .
C11 C 0.37893(9) 1.02153(6) 0.33548(3) 0.01582(14) Uani 1 1 d . . . . .
C7 C 0.49539(10) 0.91200(6) 0.40996(4) 0.01909(16) Uani 1 1 d . . . . .
H7A H 0.4642 0.8741 0.4434 0.023 Uiso 1 1 calc R U . . .
H7B H 0.4964 0.8703 0.3756 0.023 Uiso 1 1 calc R U . . .
C12 C 0.45793(9) 1.08747(6) 0.30319(4) 0.01795(15) Uani 1 1 d . . . . .
H12 H 0.5261 1.1242 0.3221 0.022 Uiso 1 1 calc R U . . .
C2 C 0.73740(9) 1.11308(7) 0.44928(3) 0.01774(15) Uani 1 1 d . . . . .
H2 H 0.7273 1.1790 0.4586 0.021 Uiso 1 1 calc R U . . .
C13 C 0.43750(10) 1.10008(7) 0.24277(4) 0.02190(17) Uani 1 1 d . . . . .
C5 C 0.76765(10) 0.91306(7) 0.42148(4) 0.02121(17) Uani 1 1 d . . . . .
H5 H 0.7777 0.8471 0.4123 0.025 Uiso 1 1 calc R U . . .
C9 C 0.42526(9) 1.17246(6) 0.44275(3) 0.01736(15) Uani 1 1 d . . . . .
C3 C 0.86847(9) 1.06798(7) 0.45003(4) 0.02151(17) Uani 1 1 d . . . . .
H3 H 0.9467 1.1046 0.4601 0.026 Uiso 1 1 calc R U . . .
C16 C 0.27683(9) 0.96549(6) 0.30670(4) 0.01907(16) Uani 1 1 d . . . . .
C14 C 0.33535(12) 1.04393(7) 0.21569(4) 0.02561(19) Uani 1 1 d . . . . .
H14 H 0.3200 1.0515 0.1758 0.031 Uiso 1 1 calc R U . . .
C10 C 0.27154(10) 1.18682(8) 0.43122(4) 0.02330(18) Uani 1 1 d . . . . .
H10A H 0.2184 1.1487 0.4586 0.035 Uiso 1 1 calc R U . . .
H10B H 0.2501 1.1661 0.3921 0.035 Uiso 1 1 calc R U . . .
H10C H 0.2483 1.2548 0.4357 0.035 Uiso 1 1 calc R U . . .
C4 C 0.88422(10) 0.96941(8) 0.43600(4) 0.02328(18) Uani 1 1 d . . . . .
H4 H 0.9725 0.9411 0.4363 0.028 Uiso 1 1 calc R U . . .
C15 C 0.25529(11) 0.97653(7) 0.24679(4) 0.02433(18) Uani 1 1 d . . . . .
H15 H 0.1880 0.9392 0.2277 0.029 Uiso 1 1 calc R U . . .
C18 C 0.52741(13) 1.17007(8) 0.20825(4) 0.0313(2) Uani 1 1 d . . . . .
H18A H 0.6216 1.1461 0.2072 0.047 Uiso 1 1 calc R U . . .
H18B H 0.5257 1.2334 0.2265 0.047 Uiso 1 1 calc R U . . .
H18C H 0.4922 1.1752 0.1690 0.047 Uiso 1 1 calc R U . . .
C17 C 0.09730(11) 0.84528(8) 0.31532(5) 0.0302(2) Uani 1 1 d . . . . .
H17A H 0.0313 0.8873 0.2962 0.045 Uiso 1 1 calc R U . . .
H17B H 0.0504 0.8074 0.3447 0.045 Uiso 1 1 calc R U . . .
H17C H 0.1387 0.8021 0.2871 0.045 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 C16 1.3677(11) . ?
O1 C17 1.4249(11) . ?
O2 C9 1.2280(11) . ?
N1 C9 1.3672(11) . ?
N1 C1 1.4164(10) . ?
N1 C8 1.4805(10) . ?
C6 C5 1.3850(12) . ?
C6 C1 1.4006(11) . ?
C6 C7 1.5062(12) . ?
C8 C11 1.5170(11) . ?
C8 C7 1.5516(12) . ?
C1 C2 1.3924(11) . ?
C11 C12 1.3886(12) . ?
C11 C16 1.4054(11) . ?
C12 C13 1.4050(12) . ?
C2 C3 1.3988(12) . ?
C13 C14 1.3888(15) . ?
C13 C18 1.5093(14) . ?
C5 C4 1.3964(14) . ?
C9 C10 1.5090(12) . ?
C3 C4 1.3921(14) . ?
C16 C15 1.3924(12) . ?
C14 C15 1.3932(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
C16 O1 C17 117.38(8) . . ?
C9 N1 C1 125.86(7) . . ?
C9 N1 C8 124.32(7) . . ?
C1 N1 C8 109.62(6) . . ?
C5 C6 C1 120.10(8) . . ?
C5 C6 C7 130.09(8) . . ?
C1 C6 C7 109.76(7) . . ?
N1 C8 C11 112.20(6) . . ?
N1 C8 C7 103.52(6) . . ?
C11 C8 C7 110.78(7) . . ?
C2 C1 C6 121.35(8) . . ?
C2 C1 N1 129.32(8) . . ?
C6 C1 N1 109.32(7) . . ?
C12 C11 C16 118.95(8) . . ?
C12 C11 C8 123.25(7) . . ?
C16 C11 C8 117.74(7) . . ?
C6 C7 C8 102.90(6) . . ?
C11 C12 C13 121.71(8) . . ?
C1 C2 C3 117.75(8) . . ?
C14 C13 C12 117.92(9) . . ?
C14 C13 C18 121.28(9) . . ?
C12 C13 C18 120.77(9) . . ?
C6 C5 C4 119.35(8) . . ?
O2 C9 N1 121.68(8) . . ?
O2 C9 C10 121.39(8) . . ?
N1 C9 C10 116.93(8) . . ?
C4 C3 C2 121.36(8) . . ?
O1 C16 C15 124.82(8) . . ?
O1 C16 C11 114.90(7) . . ?
C15 C16 C11 120.27(8) . . ?
C13 C14 C15 121.71(8) . . ?
C3 C4 C5 120.07(8) . . ?
C16 C15 C14 119.43(8) . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_11c
_database_code_depnum_ccdc_archive 'CCDC 1450299'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 N O3'
_chemical_formula_sum            'C28 H25 N O3'
_chemical_formula_weight         423.49

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                   7.7189(4)
_cell_length_b                   9.7482(5)
_cell_length_c                   29.5931(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.235(2)
_cell_angle_gamma                90
_cell_volume                     2220.66(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9718
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.27

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9453
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(1)
_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            76548
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.200
_diffrn_reflns_theta_max         31.318
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7273
_reflns_number_gt                6212
_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    ?
_computing_publication_material  ?
_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)+(0.0565P)²+1.0500P] 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_number_reflns         7273
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.41672(13) 0.73079(11) 0.52825(3) 0.01448(19) Uani 1 1 d . . . . .
C2 C 0.33355(15) 0.68976(12) 0.48731(4) 0.0186(2) Uani 1 1 d . . . . .
H2 H 0.3446 0.5994 0.4758 0.022 Uiso 1 1 calc R U . . .
C3 C 0.23287(16) 0.78939(13) 0.46416(4) 0.0226(2) Uani 1 1 d . . . . .
H3 H 0.1722 0.7664 0.4361 0.027 Uiso 1 1 calc R U . . .
C4 C 0.21882(16) 0.92260(13) 0.48120(4) 0.0227(2) Uani 1 1 d . . . . .
H4 H 0.1468 0.9873 0.4648 0.027 Uiso 1 1 calc R U . . .
C5 C 0.30792(15) 0.96195(12) 0.52153(4) 0.0194(2) Uani 1 1 d . . . . .
H5 H 0.2997 1.0531 0.5326 0.023 Uiso 1 1 calc R U . . .
C6 C 0.41016(13) 0.86407(11) 0.54551(3) 0.01484(19) Uani 1 1 d . . . . .
C7 C 0.51783(13) 0.86308(11) 0.58774(3) 0.01450(19) Uani 1 1 d . . . . .
C8 C 0.57378(13) 0.73237(11) 0.59336(3) 0.01386(18) Uani 1 1 d . . . . .
C9 C 0.55686(15) 0.98050(11) 0.61943(4) 0.0192(2) Uani 1 1 d . . . . .
H9A H 0.4659 0.9871 0.6407 0.029 Uiso 1 1 calc R U . . .
H9B H 0.5608 1.0659 0.6020 0.029 Uiso 1 1 calc R U . . .
H9C H 0.6694 0.9654 0.6362 0.029 Uiso 1 1 calc R U . . .
C10 C 0.97804(15) 0.38976(12) 0.63084(4) 0.0178(2) Uani 1 1 d . . . . .
C11 C 1.05134(17) 0.26876(13) 0.64739(4) 0.0245(2) Uani 1 1 d . . . . .
H11 H 1.0059 0.2200 0.6717 0.029 Uiso 1 1 calc R U . . .
C12 C 1.19565(17) 0.22283(13) 0.62633(4) 0.0266(3) Uani 1 1 d . . . . .
H12 H 1.2509 0.1402 0.6365 0.032 Uiso 1 1 calc R U . . .
C13 C 1.26148(16) 0.29537(13) 0.59058(4) 0.0235(2) Uani 1 1 d . . . . .
H13 H 1.3617 0.2619 0.5774 0.028 Uiso 1 1 calc R U . . .
C14 C 1.18342(14) 0.41519(12) 0.57401(4) 0.0196(2) Uani 1 1 d . . . . .
H14 H 1.2278 0.4635 0.5495 0.023 Uiso 1 1 calc R U . . .
C15 C 1.03727(14) 0.46274(11) 0.59453(4) 0.0159(2) Uani 1 1 d . . . . .
C16 C 0.92275(13) 0.57948(11) 0.58754(4) 0.01545(19) Uani 1 1 d . . . . .
C17 C 0.80644(14) 0.56877(11) 0.61953(3) 0.01482(19) Uani 1 1 d . . . . .
C18 C 0.94003(16) 0.68846(13) 0.55256(4) 0.0230(2) Uani 1 1 d . . . . .
H18A H 0.8421 0.7523 0.5530 0.035 Uiso 1 1 calc R U . . .
H18B H 0.9402 0.6460 0.5225 0.035 Uiso 1 1 calc R U . . .
H18C H 1.0491 0.7384 0.5592 0.035 Uiso 1 1 calc R U . . .
C19 C 0.66458(13) 0.66226(11) 0.63311(3) 0.01389(18) Uani 1 1 d . . . . .
H19 H 0.7209 0.7353 0.6529 0.017 Uiso 1 1 calc R U . . .
C20 C 0.52767(14) 0.58952(11) 0.66118(3) 0.01515(19) Uani 1 1 d . . . . .
H20A H 0.4518 0.5301 0.6411 0.018 Uiso 1 1 calc R U . . .
H20B H 0.5873 0.5313 0.6849 0.018 Uiso 1 1 calc R U . . .
C21 C 0.41986(13) 0.69717(11) 0.68278(3) 0.01470(19) Uani 1 1 d . . . . .
C22 C 0.25743(14) 0.73617(13) 0.66284(4) 0.0206(2) Uani 1 1 d . . . . .
H22 H 0.2079 0.6865 0.6375 0.025 Uiso 1 1 calc R U . . .
C23 C 0.16721(15) 0.84640(14) 0.67954(4) 0.0247(2) Uani 1 1 d . . . . .
H23 H 0.0572 0.8717 0.6655 0.030 Uiso 1 1 calc R U . . .
C24 C 0.23787(15) 0.91943(13) 0.71673(4) 0.0230(2) Uani 1 1 d . . . . .
H24 H 0.1777 0.9962 0.7277 0.028 Uiso 1 1 calc R U . . .
C25 C 0.39658(15) 0.88026(12) 0.73794(4) 0.0181(2) Uani 1 1 d . . . . .
H25 H 0.4439 0.9288 0.7638 0.022 Uiso 1 1 calc R U . . .
C26 C 0.48660(13) 0.76915(11) 0.72109(3) 0.01408(19) Uani 1 1 d . . . . .
C27 C 0.78336(14) 0.80998(11) 0.75475(3) 0.01518(19) Uani 1 1 d . . . . .
C28 C 0.93101(16) 0.74350(12) 0.78271(4) 0.0230(2) Uani 1 1 d . . . . .
H28A H 1.0417 0.7736 0.7718 0.034 Uiso 1 1 calc R U . . .
H28B H 0.9214 0.6436 0.7800 0.034 Uiso 1 1 calc R U . . .
H28C H 0.9262 0.7701 0.8145 0.034 Uiso 1 1 calc R U . . .
N1 N 0.64677(12) 0.72579(9) 0.74370(3) 0.01446(17) Uani 1 1 d . . . . .
H1 H 0.6578 0.6385 0.7510 0.017 Uiso 1 1 calc R U . . .
O1 O 0.51540(10) 0.64767(8) 0.55760(2) 0.01491(15) Uani 1 1 d . . . . .
O2 O 0.83610(11) 0.45371(8) 0.64671(3) 0.01859(16) Uani 1 1 d . . . . .
O3 O 0.78519(11) 0.93148(8) 0.74323(3) 0.01975(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3760(12) . ?
C1 C2 1.3875(14) . ?
C1 C6 1.3983(15) . ?
C2 C3 1.3921(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4002(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3868(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3979(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4487(14) . ?
C7 C8 1.3518(14) . ?
C7 C9 1.4962(15) . ?
C8 O1 1.3908(12) . ?
C8 C19 1.4902(14) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O2 1.3731(13) . ?
C10 C11 1.3821(16) . ?
C10 C15 1.3937(16) . ?
C11 C12 1.3900(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3989(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3871(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3991(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.4465(15) . ?
C16 C17 1.3562(15) . ?
C16 C18 1.4960(16) . ?
C17 O2 1.3893(13) . ?
C17 C19 1.5020(14) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.5618(15) . ?
C19 H19 1.0000 . ?
C20 C21 1.5102(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.3983(15) . ?
C21 C26 1.3989(14) . ?
C22 C23 1.3909(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.3881(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.3881(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3984(15) . ?
C25 H25 0.9500 . ?
C26 N1 1.4257(13) . ?
C27 O3 1.2329(13) . ?
C27 N1 1.3569(14) . ?
C27 C28 1.5047(15) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 H1 0.8800 . ?

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
O1 C1 C2 125.47(10) . . ?
O1 C1 C6 110.48(9) . . ?
C2 C1 C6 124.06(10) . . ?
C1 C2 C3 115.73(11) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 H2 122.1 . . ?
C2 C3 C4 121.67(10) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.32(11) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.27(11) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 118.88(10) . . ?
C5 C6 C7 135.14(10) . . ?
C1 C6 C7 105.96(9) . . ?
C8 C7 C6 105.67(9) . . ?
C8 C7 C9 126.60(10) . . ?
C6 C7 C9 127.71(9) . . ?
C7 C8 O1 112.54(9) . . ?
C7 C8 C19 131.06(9) . . ?
O1 C8 C19 115.82(9) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 125.62(11) . . ?
O2 C10 C15 110.33(9) . . ?
C11 C10 C15 124.04(11) . . ?
C10 C11 C12 115.89(12) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 H11 122.1 . . ?
C11 C12 C13 121.61(11) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 121.36(11) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 117.95(11) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C10 C15 C14 119.11(10) . . ?
C10 C15 C16 106.27(9) . . ?
C14 C15 C16 134.61(11) . . ?
C17 C16 C15 105.58(9) . . ?
C17 C16 C18 129.43(10) . . ?
C15 C16 C18 124.96(10) . . ?
C16 C17 O2 112.15(9) . . ?
C16 C17 C19 132.33(10) . . ?
O2 C17 C19 115.29(9) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 C17 112.13(8) . . ?
C8 C19 C20 109.32(8) . . ?
C17 C19 C20 113.71(9) . . ?
C8 C19 H19 107.1 . . ?
C17 C19 H19 107.1 . . ?
C20 C19 H19 107.1 . . ?
C21 C20 C19 108.98(8) . . ?
C21 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
C22 C21 C26 118.08(10) . . ?
C22 C21 C20 121.02(10) . . ?
C26 C21 C20 120.67(9) . . ?
C23 C22 C21 121.13(11) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 120.01(11) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.96(11) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 119.80(11) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C21 120.96(10) . . ?
C25 C26 N1 119.92(9) . . ?
C21 C26 N1 119.10(9) . . ?
O3 C27 N1 122.61(10) . . ?
O3 C27 C28 122.83(10) . . ?
N1 C27 C28 114.55(9) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 N1 C26 124.42(9) . . ?
C27 N1 H1 117.8 . . ?
C26 N1 H1 117.8 . . ?
C1 O1 C8 105.30(8) . . ?
C10 O2 C17 105.67(8) . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_13b
_database_code_depnum_ccdc_archive 'CCDC 1450300'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H16 Br N O'
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         342.23

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.9573(3)
_cell_length_b                   9.6303(3)
_cell_length_c                   10.5963(3)
_cell_angle_alpha                68.1470(10)
_cell_angle_beta                 75.128(2)
_cell_angle_gamma                69.3120(10)
_cell_volume                     697.70(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    6669
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      30.63
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.944
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3714
_exptl_absorpt_correction_T_max  0.6128
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '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            13259
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         30.685
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4228
_reflns_number_gt                3719
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0311P)²+0.2935P] 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_number_reflns         4228
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.0634(2) -0.24152(19) 0.44377(16) 0.0128(3) Uani 1 1 d . . . . .
H1 H -0.0368 -0.2200 0.4025 0.015 Uiso 1 1 calc R U . . .
C2 C 0.1637(2) -0.13568(19) 0.39984(16) 0.0124(3) Uani 1 1 d . . . . .
C3 C 0.3163(2) -0.16342(18) 0.45746(16) 0.0113(3) Uani 1 1 d . . . . .
H3 H 0.3831 -0.0919 0.4260 0.014 Uiso 1 1 calc R U . . .
C4 C 0.3644(2) -0.30077(18) 0.56273(15) 0.0096(3) Uani 1 1 d . . . . .
C5 C 0.2635(2) -0.40728(18) 0.60860(15) 0.0096(3) Uani 1 1 d . . . . .
C6 C 0.1131(2) -0.38032(19) 0.55009(16) 0.0116(3) Uani 1 1 d . . . . .
H6 H 0.0474 -0.4526 0.5808 0.014 Uiso 1 1 calc R U . . .
C7 C 0.3276(2) -0.24722(18) 0.87026(15) 0.0099(3) Uani 1 1 d . . . . .
C8 C 0.2165(2) -0.18042(19) 0.97106(17) 0.0126(3) Uani 1 1 d . . . . .
H8 H 0.2140 -0.0808 0.9649 0.015 Uiso 1 1 calc R U . . .
C9 C 0.1106(2) -0.2589(2) 1.07941(16) 0.0135(3) Uani 1 1 d . . . . .
H9 H 0.0381 -0.2128 1.1455 0.016 Uiso 1 1 calc R U . . .
C10 C 0.1133(2) -0.4069(2) 1.08879(16) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.0417 -0.4605 1.1609 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2233(2) -0.47501(18) 0.98999(16) 0.0113(3) Uani 1 1 d . . . . .
H11 H 0.2249 -0.5747 0.9971 0.014 Uiso 1 1 calc R U . . .
C12 C 0.3314(2) -0.39730(18) 0.88035(15) 0.0094(3) Uani 1 1 d . . . . .
C13 C 0.4489(2) -0.47797(17) 0.77508(15) 0.0089(3) Uani 1 1 d . . . . .
H13 H 0.5490 -0.5654 0.8156 0.011 Uiso 1 1 calc R U . . .
C14 C 0.5218(2) -0.36530(18) 0.64333(15) 0.0093(3) Uani 1 1 d . . . . .
H14 H 0.6258 -0.4268 0.5949 0.011 Uiso 1 1 calc R U . . .
C15 C 0.5828(2) -0.24726(18) 0.67008(16) 0.0118(3) Uani 1 1 d . . . . .
H15A H 0.6237 -0.1782 0.5831 0.014 Uiso 1 1 calc R U . . .
H15B H 0.6845 -0.3018 0.7215 0.014 Uiso 1 1 calc R U . . .
C16 C 0.4307(2) -0.15083(19) 0.74995(16) 0.0134(3) Uani 1 1 d . . . . .
H16A H 0.4817 -0.0955 0.7834 0.016 Uiso 1 1 calc R U . . .
H16B H 0.3465 -0.0735 0.6882 0.016 Uiso 1 1 calc R U . . .
C17 C 0.3297(2) -0.68234(18) 0.75322(16) 0.0111(3) Uani 1 1 d . . . . .
C18 C 0.4220(2) -0.80555(19) 0.87176(17) 0.0153(3) Uani 1 1 d . . . . .
H18A H 0.3453 -0.8708 0.9266 0.023 Uiso 1 1 calc R U . . .
H18B H 0.4442 -0.7562 0.9271 0.023 Uiso 1 1 calc R U . . .
H18C H 0.5352 -0.8681 0.8370 0.023 Uiso 1 1 calc R U . . .
N1 N 0.33645(18) -0.53331(15) 0.72144(13) 0.0096(2) Uani 1 1 d . . . . .
O1 O 0.24961(16) -0.71554(14) 0.68885(12) 0.0139(2) Uani 1 1 d . . . . .
Br1 Br 0.09101(2) 0.05346(2) 0.25698(2) 0.01702(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.395(2) . ?
C2 C3 1.396(2) . ?
C2 Br1 1.8964(15) . ?
C3 C4 1.380(2) . ?
C4 C5 1.394(2) . ?
C4 C14 1.513(2) . ?
C5 C6 1.387(2) . ?
C5 N1 1.4205(19) . ?
C7 C12 1.399(2) . ?
C7 C8 1.400(2) . ?
C7 C16 1.510(2) . ?
C8 C9 1.381(2) . ?
C9 C10 1.384(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.523(2) . ?
C13 N1 1.4938(18) . ?
C13 C14 1.538(2) . ?
C14 C15 1.519(2) . ?
C15 C16 1.519(2) . ?
C17 O1 1.2262(19) . ?
C17 N1 1.364(2) . ?
C17 C18 1.508(2) . ?

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 119.82(14) . . ?
C1 C2 C3 122.24(15) . . ?
C1 C2 Br1 118.96(11) . . ?
C3 C2 Br1 118.80(12) . . ?
C4 C3 C2 117.57(15) . . ?
C3 C4 C5 120.68(14) . . ?
C3 C4 C14 130.23(14) . . ?
C5 C4 C14 109.08(13) . . ?
C6 C5 C4 121.65(14) . . ?
C6 C5 N1 129.32(14) . . ?
C4 C5 N1 108.98(13) . . ?
C5 C6 C1 118.03(15) . . ?
C12 C7 C8 118.97(14) . . ?
C12 C7 C16 122.24(14) . . ?
C8 C7 C16 118.69(14) . . ?
C9 C8 C7 121.56(15) . . ?
C8 C9 C10 119.47(15) . . ?
C9 C10 C11 119.66(15) . . ?
C10 C11 C12 121.47(15) . . ?
C11 C12 C7 118.87(14) . . ?
C11 C12 C13 119.02(14) . . ?
C7 C12 C13 122.11(14) . . ?
N1 C13 C12 110.23(12) . . ?
N1 C13 C14 101.88(11) . . ?
C12 C13 C14 112.82(12) . . ?
C4 C14 C15 116.72(13) . . ?
C4 C14 C13 100.91(12) . . ?
C15 C14 C13 113.47(12) . . ?
C14 C15 C16 111.74(13) . . ?
C7 C16 C15 113.41(13) . . ?
O1 C17 N1 121.38(14) . . ?
O1 C17 C18 120.69(14) . . ?
N1 C17 C18 117.93(13) . . ?
C17 N1 C5 124.05(13) . . ?
C17 N1 C13 127.92(12) . . ?
C5 N1 C13 106.92(12) . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

