# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1583075'
_audit_update_record             
;
2017-10-31 deposited with the CCDC.
2018-04-02 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         ?
_chemical_formula_sum            'C31 H30 Br N3 O5'
_chemical_formula_weight         604.49

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'
Br Br -0.2901 2.4595 '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/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                   12.0254(6)
_cell_length_b                   15.9496(9)
_cell_length_c                   16.7865(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.616(3)
_cell_angle_gamma                90
_cell_volume                     2903.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_process_details   SADABS_Bruker_2014

_diffrn_ambient_temperature      293(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            95862
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_av_R_equivalents  0.1338
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         33.833
_diffrn_reflns_theta_full        25.242
_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             11677
_reflns_number_gt                6536
_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 (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)+(0.1384P)²+5.4193P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11677
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0907
_refine_ls_wR_factor_ref         0.2789
_refine_ls_wR_factor_gt          0.2317
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.44192(4) -0.23413(3) 0.26318(3) 0.04130(16) Uani 1 1 d . . . . .
O1 O -0.0876(4) -0.56517(19) 0.3904(2) 0.0526(11) Uani 1 1 d . . . . .
O2 O -0.1449(2) -0.30620(14) 0.19161(14) 0.0171(4) Uani 1 1 d . . . . .
N1 N -0.1023(3) -0.57831(16) 0.21141(18) 0.0203(5) Uani 1 1 d . . . . .
N2 N -0.2849(5) -0.5130(2) 0.3142(3) 0.0444(10) Uani 1 1 d . . . . .
H2B H -0.3112 -0.5197 0.3539 0.053 Uiso 1 1 calc R U . . .
N3 N -0.1114(3) -0.3146(2) 0.47271(18) 0.0296(7) Uani 1 1 d . . . . .
H2 H -0.0931 -0.3260 0.5180 0.036 Uiso 1 1 d R U . . .
C1 C -0.1577(3) -0.50966(19) 0.2401(2) 0.0193(6) Uani 1 1 d . . . . .
C2 C -0.0620(3) -0.43772(18) 0.25735(19) 0.0155(5) Uani 1 1 d . . . . .
H2A H 0.0095 -0.4479 0.3139 0.019 Uiso 1 1 calc R U . . .
C3 C -0.0232(3) -0.44886(18) 0.18175(19) 0.0148(5) Uani 1 1 d . . . . .
H3A H -0.0895 -0.4269 0.1275 0.018 Uiso 1 1 calc R U . . .
C4 C -0.0200(3) -0.5442(2) 0.1727(2) 0.0194(6) Uani 1 1 d . . . . .
H4A H 0.0644 -0.5643 0.2075 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0694(4) -0.5809(2) 0.0797(2) 0.0244(7) Uani 1 1 d . . . . .
H5A H -0.1306 -0.5444 0.0370 0.029 Uiso 1 1 calc R U . . .
H5B H -0.0033 -0.5903 0.0622 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1267(4) -0.6635(2) 0.0888(2) 0.0274(7) Uani 1 1 d . . . . .
H6A H -0.1881 -0.6827 0.0319 0.033 Uiso 1 1 calc R U . . .
H6B H -0.0642 -0.7066 0.1143 0.033 Uiso 1 1 calc R U . . .
C7 C -0.1856(4) -0.6421(2) 0.1504(3) 0.0270(7) Uani 1 1 d . . . . .
H7A H -0.2679 -0.6195 0.1175 0.032 Uiso 1 1 calc R U . . .
H7B H -0.1907 -0.6913 0.1826 0.032 Uiso 1 1 calc R U . . .
C8 C -0.2892(3) -0.4801(2) 0.1811(3) 0.0235(7) Uani 1 1 d . . . . .
C9 C -0.3424(3) -0.4487(2) 0.0965(3) 0.0269(7) Uani 1 1 d . . . . .
H9A H -0.2993 -0.4501 0.0619 0.032 Uiso 1 1 calc R U . . .
C10 C -0.4616(4) -0.4148(3) 0.0624(4) 0.0415(11) Uani 1 1 d . . . . .
H10A H -0.4967 -0.3932 0.0054 0.050 Uiso 1 1 calc R U . . .
C11 C -0.5264(4) -0.4130(3) 0.1113(4) 0.0471(12) Uani 1 1 d . . . . .
H11A H -0.6049 -0.3896 0.0878 0.057 Uiso 1 1 calc R U . . .
C12 C -0.4777(5) -0.4453(3) 0.1946(5) 0.0535(16) Uani 1 1 d . . . . .
H12A H -0.5232 -0.4453 0.2274 0.064 Uiso 1 1 calc R U . . .
C13 C -0.3560(4) -0.4791(2) 0.2307(3) 0.0359(10) Uani 1 1 d . . . . .
C14 C -0.1699(5) -0.5340(2) 0.3254(3) 0.0366(10) Uani 1 1 d . . . . .
C15 C -0.1127(3) -0.35055(18) 0.25869(18) 0.0147(5) Uani 1 1 d . . . . .
C16 C -0.1254(3) -0.32223(19) 0.33548(18) 0.0174(6) Uani 1 1 d . . . . .
C17 C -0.0798(4) -0.3599(2) 0.4181(2) 0.0273(8) Uani 1 1 d . . . . .
H17A H -0.0341 -0.4092 0.4334 0.033 Uiso 1 1 calc R U . . .
C18 C -0.1802(3) -0.2456(2) 0.4285(2) 0.0208(6) Uani 1 1 d . . . . .
C19 C -0.2327(3) -0.1825(2) 0.4586(2) 0.0221(6) Uani 1 1 d . . . . .
H19A H -0.2259 -0.1825 0.5159 0.027 Uiso 1 1 calc R U . . .
C20 C -0.2956(3) -0.1197(2) 0.3990(2) 0.0219(6) Uani 1 1 d . . . . .
H20A H -0.3307 -0.0761 0.4171 0.026 Uiso 1 1 calc R U . . .
C21 C -0.3074(3) -0.1205(2) 0.3124(2) 0.0211(6) Uani 1 1 d . . . . .
H21A H -0.3506 -0.0776 0.2740 0.025 Uiso 1 1 calc R U . . .
C22 C -0.2563(3) -0.18385(19) 0.2828(2) 0.0168(6) Uani 1 1 d . . . . .
H22A H -0.2654 -0.1839 0.2249 0.020 Uiso 1 1 calc R U . . .
C23 C -0.1906(3) -0.24776(18) 0.3410(2) 0.0154(5) Uani 1 1 d . . . . .
C24 C 0.0937(3) -0.4015(2) 0.1979(2) 0.0182(6) Uani 1 1 d . . . . .
C25 C 0.0895(3) -0.3336(2) 0.1448(2) 0.0214(6) Uani 1 1 d . . . . .
H25A H 0.0158 -0.3212 0.0962 0.026 Uiso 1 1 calc R U . . .
C26 C 0.1924(4) -0.2837(2) 0.1623(3) 0.0273(7) Uani 1 1 d . . . . .
H26A H 0.1875 -0.2379 0.1266 0.033 Uiso 1 1 calc R U . . .
C27 C 0.3019(3) -0.3035(3) 0.2339(3) 0.0277(8) Uani 1 1 d . . . . .
C28 C 0.3104(3) -0.3724(3) 0.2863(3) 0.0309(8) Uani 1 1 d . . . . .
H28A H 0.3852 -0.3862 0.3332 0.037 Uiso 1 1 calc R U . . .
C29 C 0.2060(3) -0.4212(2) 0.2683(3) 0.0271(7) Uani 1 1 d . . . . .
H29A H 0.2114 -0.4673 0.3037 0.033 Uiso 1 1 calc R U . . .
O3 O -0.3669(7) -0.3983(4) 0.5614(3) 0.0454(18) Uani 0.5 1 d . . P . .
C30 C -0.4235(8) -0.3141(6) 0.5275(5) 0.038(2) Uani 0.5 1 d . . P . .
H30A H -0.4269 -0.3047 0.4694 0.046 Uiso 0.5 1 calc R U P . .
H30B H -0.3726 -0.2705 0.5667 0.046 Uiso 0.5 1 calc R U P . .
C33 C -0.5575(11) -0.3092(8) 0.5219(8) 0.054(3) Uiso 0.5 1 d . . P . .
H33A H -0.6104 -0.2795 0.4694 0.080 Uiso 0.5 1 calc R U P . .
H33B H -0.5551 -0.2802 0.5728 0.080 Uiso 0.5 1 calc R U P . .
H33C H -0.5888 -0.3649 0.5202 0.080 Uiso 0.5 1 calc R U P . .
O1W O -0.1082(3) -0.15077(17) 0.13937(17) 0.0405(8) Uani 1 1 d . . . . .
H1 H -0.1107 -0.1841 0.1749 0.061 Uiso 1 1 d R U . . .
O2W O -0.4282(8) -0.5076(4) 0.4149(4) 0.123(3) 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
Br1 C27 1.893(4) . ?
O1 C14 1.218(6) . ?
O2 C15 1.241(4) . ?
N1 C1 1.467(4) . ?
N1 C7 1.483(5) . ?
N1 C4 1.502(4) . ?
N2 C14 1.355(7) . ?
N2 C13 1.397(7) . ?
N2 H2B 0.8600 . ?
N3 C17 1.345(4) . ?
N3 C18 1.385(4) . ?
N3 H2 0.7177 . ?
C1 C8 1.533(5) . ?
C1 C14 1.551(5) . ?
C1 C2 1.561(5) . ?
C2 C15 1.522(4) . ?
C2 C3 1.541(4) . ?
C2 H2A 0.9800 . ?
C3 C24 1.512(4) . ?
C3 C4 1.531(4) . ?
C3 H3A 0.9800 . ?
C4 C5 1.526(4) . ?
C4 H4A 0.9800 . ?
C5 C6 1.525(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.524(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.375(6) . ?
C8 C13 1.384(5) . ?
C9 C10 1.402(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.355(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.361(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.425(7) . ?
C12 H12A 0.9300 . ?
C15 C16 1.435(4) . ?
C16 C17 1.388(4) . ?
C16 C23 1.448(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.393(5) . ?
C18 C23 1.420(4) . ?
C19 C20 1.385(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.398(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.383(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.396(4) . ?
C22 H22A 0.9300 . ?
C24 C25 1.390(5) . ?
C24 C29 1.392(5) . ?
C25 C26 1.392(5) . ?
C25 H25A 0.9300 . ?
C26 C27 1.382(6) . ?
C26 H26A 0.9300 . ?
C27 C28 1.384(6) . ?
C28 C29 1.395(5) . ?
C28 H28A 0.9300 . ?
C29 H29A 0.9300 . ?
O3 C30 1.502(13) . ?
C30 C33 1.575(14) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O1W H1 0.8089 . ?

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
C1 N1 C7 118.1(3) . . ?
C1 N1 C4 110.5(2) . . ?
C7 N1 C4 108.9(2) . . ?
C14 N2 C13 112.4(3) . . ?
C14 N2 H2B 123.8 . . ?
C13 N2 H2B 123.8 . . ?
C17 N3 C18 110.0(3) . . ?
C17 N3 H2 122.6 . . ?
C18 N3 H2 127.4 . . ?
N1 C1 C8 120.4(3) . . ?
N1 C1 C14 110.8(3) . . ?
C8 C1 C14 101.0(3) . . ?
N1 C1 C2 101.9(3) . . ?
C8 C1 C2 111.4(2) . . ?
C14 C1 C2 111.7(3) . . ?
C15 C2 C3 112.5(2) . . ?
C15 C2 C1 114.0(3) . . ?
C3 C2 C1 103.0(2) . . ?
C15 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C24 C3 C4 116.9(3) . . ?
C24 C3 C2 112.6(2) . . ?
C4 C3 C2 103.1(2) . . ?
C24 C3 H3A 108.0 . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
N1 C4 C5 105.4(3) . . ?
N1 C4 C3 105.5(2) . . ?
C5 C4 C3 117.9(3) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C6 C5 C4 102.8(3) . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C7 C6 C5 103.7(3) . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
N1 C7 C6 104.4(3) . . ?
N1 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C13 119.1(4) . . ?
C9 C8 C1 131.9(3) . . ?
C13 C8 C1 108.7(4) . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9A 120.1 . . ?
C10 C9 H9A 120.1 . . ?
C11 C10 C9 121.1(5) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C8 C13 N2 109.7(4) . . ?
C8 C13 C12 120.3(5) . . ?
N2 C13 C12 130.0(4) . . ?
O1 C14 N2 127.7(4) . . ?
O1 C14 C1 124.3(4) . . ?
N2 C14 C1 107.9(4) . . ?
O2 C15 C16 121.5(3) . . ?
O2 C15 C2 118.5(3) . . ?
C16 C15 C2 120.0(3) . . ?
C17 C16 C15 127.7(3) . . ?
C17 C16 C23 106.4(3) . . ?
C15 C16 C23 125.9(3) . . ?
N3 C17 C16 110.0(3) . . ?
N3 C17 H17A 125.0 . . ?
C16 C17 H17A 125.0 . . ?
N3 C18 C19 129.8(3) . . ?
N3 C18 C23 107.4(3) . . ?
C19 C18 C23 122.8(3) . . ?
C20 C19 C18 116.9(3) . . ?
C20 C19 H19A 121.6 . . ?
C18 C19 H19A 121.6 . . ?
C19 C20 C21 121.5(3) . . ?
C19 C20 H20A 119.3 . . ?
C21 C20 H20A 119.3 . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22A 120.4 . . ?
C23 C22 H22A 120.4 . . ?
C22 C23 C18 118.4(3) . . ?
C22 C23 C16 135.4(3) . . ?
C18 C23 C16 106.2(3) . . ?
C25 C24 C29 118.2(3) . . ?
C25 C24 C3 120.0(3) . . ?
C29 C24 C3 121.7(3) . . ?
C24 C25 C26 121.9(3) . . ?
C24 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C27 C26 C25 118.6(4) . . ?
C27 C26 H26A 120.7 . . ?
C25 C26 H26A 120.7 . . ?
C26 C27 C28 121.0(3) . . ?
C26 C27 Br1 119.9(3) . . ?
C28 C27 Br1 119.1(3) . . ?
C27 C28 C29 119.5(4) . . ?
C27 C28 H28A 120.2 . . ?
C29 C28 H28A 120.2 . . ?
C24 C29 C28 120.7(4) . . ?
C24 C29 H29A 119.6 . . ?
C28 C29 H29A 119.6 . . ?
O3 C30 C33 110.6(7) . . ?
O3 C30 H30A 109.5 . . ?
C33 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
C33 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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 N1 C1 C8 -27.7(4) . . . . ?
C4 N1 C1 C8 98.6(3) . . . . ?
C7 N1 C1 C14 89.6(4) . . . . ?
C4 N1 C1 C14 -144.1(3) . . . . ?
C7 N1 C1 C2 -151.5(3) . . . . ?
C4 N1 C1 C2 -25.2(3) . . . . ?
N1 C1 C2 C15 160.8(2) . . . . ?
C8 C1 C2 C15 31.1(3) . . . . ?
C14 C1 C2 C15 -80.9(3) . . . . ?
N1 C1 C2 C3 38.6(3) . . . . ?
C8 C1 C2 C3 -91.1(3) . . . . ?
C14 C1 C2 C3 156.8(3) . . . . ?
C15 C2 C3 C24 72.3(3) . . . . ?
C1 C2 C3 C24 -164.5(3) . . . . ?
C15 C2 C3 C4 -160.8(3) . . . . ?
C1 C2 C3 C4 -37.7(3) . . . . ?
C1 N1 C4 C5 -123.5(3) . . . . ?
C7 N1 C4 C5 7.9(3) . . . . ?
C1 N1 C4 C3 2.0(3) . . . . ?
C7 N1 C4 C3 133.3(3) . . . . ?
C24 C3 C4 N1 146.6(3) . . . . ?
C2 C3 C4 N1 22.6(3) . . . . ?
C24 C3 C4 C5 -96.1(4) . . . . ?
C2 C3 C4 C5 139.9(3) . . . . ?
N1 C4 C5 C6 -28.5(3) . . . . ?
C3 C4 C5 C6 -145.8(3) . . . . ?
C4 C5 C6 C7 38.4(4) . . . . ?
C1 N1 C7 C6 143.2(3) . . . . ?
C4 N1 C7 C6 16.1(4) . . . . ?
C5 C6 C7 N1 -33.8(4) . . . . ?
N1 C1 C8 C9 -58.9(5) . . . . ?
C14 C1 C8 C9 179.0(4) . . . . ?
C2 C1 C8 C9 60.3(5) . . . . ?
N1 C1 C8 C13 128.4(3) . . . . ?
C14 C1 C8 C13 6.2(3) . . . . ?
C2 C1 C8 C13 -112.5(3) . . . . ?
C13 C8 C9 C10 1.4(5) . . . . ?
C1 C8 C9 C10 -170.7(3) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C9 C10 C11 C12 -0.9(7) . . . . ?
C10 C11 C12 C13 1.6(7) . . . . ?
C9 C8 C13 N2 -179.5(3) . . . . ?
C1 C8 C13 N2 -5.7(4) . . . . ?
C9 C8 C13 C12 -0.7(5) . . . . ?
C1 C8 C13 C12 173.2(3) . . . . ?
C14 N2 C13 C8 2.6(5) . . . . ?
C14 N2 C13 C12 -176.1(4) . . . . ?
C11 C12 C13 C8 -0.9(6) . . . . ?
C11 C12 C13 N2 177.7(4) . . . . ?
C13 N2 C14 O1 -179.4(4) . . . . ?
C13 N2 C14 C1 1.7(5) . . . . ?
N1 C1 C14 O1 47.7(5) . . . . ?
C8 C1 C14 O1 176.3(4) . . . . ?
C2 C1 C14 O1 -65.2(5) . . . . ?
N1 C1 C14 N2 -133.4(3) . . . . ?
C8 C1 C14 N2 -4.7(4) . . . . ?
C2 C1 C14 N2 113.8(4) . . . . ?
C3 C2 C15 O2 16.7(4) . . . . ?
C1 C2 C15 O2 -100.1(3) . . . . ?
C3 C2 C15 C16 -164.9(3) . . . . ?
C1 C2 C15 C16 78.3(4) . . . . ?
O2 C15 C16 C17 -171.2(4) . . . . ?
C2 C15 C16 C17 10.5(5) . . . . ?
O2 C15 C16 C23 9.5(5) . . . . ?
C2 C15 C16 C23 -168.9(3) . . . . ?
C18 N3 C17 C16 0.6(5) . . . . ?
C15 C16 C17 N3 -179.7(4) . . . . ?
C23 C16 C17 N3 -0.2(4) . . . . ?
C17 N3 C18 C19 179.4(4) . . . . ?
C17 N3 C18 C23 -0.7(5) . . . . ?
N3 C18 C19 C20 178.9(4) . . . . ?
C23 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C21 1.0(5) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C21 C22 C23 C18 0.7(5) . . . . ?
C21 C22 C23 C16 -179.8(4) . . . . ?
N3 C18 C23 C22 -179.8(3) . . . . ?
C19 C18 C23 C22 0.1(5) . . . . ?
N3 C18 C23 C16 0.6(4) . . . . ?
C19 C18 C23 C16 -179.6(3) . . . . ?
C17 C16 C23 C22 -179.8(4) . . . . ?
C15 C16 C23 C22 -0.3(6) . . . . ?
C17 C16 C23 C18 -0.2(4) . . . . ?
C15 C16 C23 C18 179.2(3) . . . . ?
C4 C3 C24 C25 128.4(3) . . . . ?
C2 C3 C24 C25 -112.6(3) . . . . ?
C4 C3 C24 C29 -55.1(4) . . . . ?
C2 C3 C24 C29 63.9(4) . . . . ?
C29 C24 C25 C26 -2.5(5) . . . . ?
C3 C24 C25 C26 174.0(3) . . . . ?
C24 C25 C26 C27 1.0(5) . . . . ?
C25 C26 C27 C28 1.3(6) . . . . ?
C25 C26 C27 Br1 -177.1(3) . . . . ?
C26 C27 C28 C29 -2.0(6) . . . . ?
Br1 C27 C28 C29 176.4(3) . . . . ?
C25 C24 C29 C28 1.8(5) . . . . ?
C3 C24 C29 C28 -174.7(3) . . . . ?
C27 C28 C29 C24 0.4(6) . . . . ?

_refine_diff_density_max         2.738
_refine_diff_density_min         -1.144
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1818997'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.3388(5)
_cell_length_b                   7.1295(3)
_cell_length_c                   13.1880(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.232(2)
_cell_angle_gamma                90.00
_cell_volume                     1244.19(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8064
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      32.88


_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_process_details   SADABS_Bruker_2014

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            20212
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         33.18
_reflns_number_total             4734
_reflns_number_gt                3221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.4238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4734
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41011(7) 0.46360(13) 0.30239(7) 0.0197(2) Uani 1 1 d . . .
N1 N 0.38433(8) 0.16930(15) 0.60527(8) 0.0174(2) Uani 1 1 d . . .
C1 C 0.29136(9) 0.23980(17) 0.56258(10) 0.0158(2) Uani 1 1 d . . .
C2 C 0.19777(10) 0.22799(19) 0.59869(10) 0.0203(3) Uani 1 1 d . . .
H2A H 0.1900 0.1666 0.6612 0.024 Uiso 1 1 calc R . .
C3 C 0.11686(10) 0.3098(2) 0.53929(11) 0.0235(3) Uani 1 1 d . . .
H3A H 0.0516 0.3026 0.5607 0.028 Uiso 1 1 calc R . .
C4 C 0.12886(10) 0.4032(2) 0.44802(11) 0.0223(3) Uani 1 1 d . . .
H4A H 0.0717 0.4592 0.4094 0.027 Uiso 1 1 calc R . .
C5 C 0.22233(9) 0.41588(18) 0.41281(10) 0.0184(3) Uani 1 1 d . . .
H5A H 0.2298 0.4804 0.3512 0.022 Uiso 1 1 calc R . .
C6 C 0.30537(9) 0.33084(17) 0.47062(9) 0.0149(2) Uani 1 1 d . . .
C7 C 0.41124(9) 0.31036(17) 0.45873(9) 0.0142(2) Uani 1 1 d . . .
C8 C 0.45500(9) 0.21234(17) 0.54392(9) 0.0159(2) Uani 1 1 d . . .
H8A H 0.5245 0.1801 0.5572 0.019 Uiso 1 1 calc R . .
C9 C 0.45978(9) 0.37547(17) 0.37309(9) 0.0148(2) Uani 1 1 d . . .
C10 C 0.56755(9) 0.33212(17) 0.37015(10) 0.0163(2) Uani 1 1 d . . .
H10A H 0.6031 0.2594 0.4233 0.020 Uiso 1 1 calc R . .
C11 C 0.61590(9) 0.39371(17) 0.29373(10) 0.0166(2) Uani 1 1 d . . .
H11A H 0.5773 0.4684 0.2434 0.020 Uiso 1 1 calc R . .
C12 C 0.72120(9) 0.35979(17) 0.27839(10) 0.0165(2) Uani 1 1 d . . .
C13 C 0.75674(10) 0.43489(19) 0.19170(11) 0.0223(3) Uani 1 1 d . . .
H13A H 0.7121 0.5049 0.1442 0.027 Uiso 1 1 calc R . .
C14 C 0.85641(11) 0.4087(2) 0.17391(12) 0.0272(3) Uani 1 1 d . . .
H14A H 0.8796 0.4612 0.1148 0.033 Uiso 1 1 calc R . .
C15 C 0.92152(10) 0.3063(2) 0.24243(12) 0.0264(3) Uani 1 1 d . . .
H15A H 0.9897 0.2883 0.2306 0.032 Uiso 1 1 calc R . .
C16 C 0.88737(10) 0.2294(2) 0.32871(12) 0.0243(3) Uani 1 1 d . . .
H16A H 0.9322 0.1582 0.3755 0.029 Uiso 1 1 calc R . .
C17 C 0.78820(10) 0.25615(19) 0.34674(11) 0.0204(3) Uani 1 1 d . . .
H17A H 0.7656 0.2036 0.4060 0.024 Uiso 1 1 calc R . .
H1N1 H 0.3982(13) 0.114(3) 0.6662(14) 0.032(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
O1 C9 1.2440(15) . ?
N1 C8 1.3525(16) . ?
N1 C1 1.3899(16) . ?
N1 H1N1 0.895(18) . ?
C1 C2 1.3936(18) . ?
C1 C6 1.4086(18) . ?
C2 C3 1.380(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.402(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3871(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4010(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4478(16) . ?
C7 C8 1.3879(17) . ?
C7 C9 1.4473(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.4757(17) . ?
C10 C11 1.3372(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.4641(17) . ?
C11 H11A 0.9500 . ?
C12 C17 1.3979(18) . ?
C12 C13 1.3982(18) . ?
C13 C14 1.3914(19) . ?
C13 H13A 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3864(19) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 109.21(11) . . ?
C8 N1 H1N1 123.9(11) . . ?
C1 N1 H1N1 126.7(11) . . ?
N1 C1 C2 129.18(12) . . ?
N1 C1 C6 107.89(11) . . ?
C2 C1 C6 122.93(12) . . ?
C3 C2 C1 116.78(12) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C2 C3 C4 121.48(12) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 121.51(12) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 118.17(12) . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 H5A 120.9 . . ?
C5 C6 C1 119.11(11) . . ?
C5 C6 C7 134.41(12) . . ?
C1 C6 C7 106.48(10) . . ?
C8 C7 C6 106.24(10) . . ?
C8 C7 C9 127.55(11) . . ?
C6 C7 C9 126.19(11) . . ?
N1 C8 C7 110.17(11) . . ?
N1 C8 H8A 124.9 . . ?
C7 C8 H8A 124.9 . . ?
O1 C9 C7 119.91(11) . . ?
O1 C9 C10 120.98(11) . . ?
C7 C9 C10 119.10(11) . . ?
C11 C10 C9 120.99(12) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 127.73(12) . . ?
C10 C11 H11A 116.1 . . ?
C12 C11 H11A 116.1 . . ?
C17 C12 C13 118.33(12) . . ?
C17 C12 C11 123.01(11) . . ?
C13 C12 C11 118.66(12) . . ?
C14 C13 C12 121.07(13) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C15 C14 C13 119.75(13) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.02(13) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.26(14) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C12 120.57(13) . . ?
C16 C17 H17A 119.7 . . ?
C12 C17 H17A 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 179.58(13) . . . . ?
C8 N1 C1 C6 -0.08(14) . . . . ?
N1 C1 C2 C3 -179.19(13) . . . . ?
C6 C1 C2 C3 0.42(19) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -1.28(18) . . . . ?
C4 C5 C6 C7 178.48(13) . . . . ?
N1 C1 C6 C5 -179.50(11) . . . . ?
C2 C1 C6 C5 0.82(19) . . . . ?
N1 C1 C6 C7 0.68(13) . . . . ?
C2 C1 C6 C7 -179.00(12) . . . . ?
C5 C6 C7 C8 179.20(13) . . . . ?
C1 C6 C7 C8 -1.02(13) . . . . ?
C5 C6 C7 C9 -2.4(2) . . . . ?
C1 C6 C7 C9 177.41(11) . . . . ?
C1 N1 C8 C7 -0.60(14) . . . . ?
C6 C7 C8 N1 1.01(14) . . . . ?
C9 C7 C8 N1 -177.40(11) . . . . ?
C8 C7 C9 O1 -179.36(12) . . . . ?
C6 C7 C9 O1 2.54(19) . . . . ?
C8 C7 C9 C10 1.99(19) . . . . ?
C6 C7 C9 C10 -176.11(11) . . . . ?
O1 C9 C10 C11 3.08(19) . . . . ?
C7 C9 C10 C11 -178.29(12) . . . . ?
C9 C10 C11 C12 -178.53(11) . . . . ?
C10 C11 C12 C17 -1.4(2) . . . . ?
C10 C11 C12 C13 178.87(13) . . . . ?
C17 C12 C13 C14 -0.5(2) . . . . ?
C11 C12 C13 C14 179.29(12) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C13 C12 C17 C16 0.15(19) . . . . ?
C11 C12 C17 C16 -179.60(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        33.18
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061
