# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1530500'
_audit_update_record             
;
2017-01-31 deposited with the CCDC.
2017-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Br N O3'
_chemical_formula_weight         412.27

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   10.4368(4)
_cell_length_b                   6.0294(2)
_cell_length_c                   15.7294(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.537(4)
_cell_angle_gamma                90
_cell_volume                     943.81(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    5566
_cell_measurement_theta_min      3.6410
_cell_measurement_theta_max      24.8580

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.197
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95203
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.41q'

_exptl_special_details           
;
CrysAlisPro 1.171.38.41q (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14905
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.642
_diffrn_reflns_theta_max         29.837
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4862
_reflns_number_gt                4081
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_max     0.855
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlisPro 2015'
_computing_cell_refinement       'CrysAlisPro 2015'
_computing_data_reduction        'CrysAlisPro 2015'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0432P)²+0.2194P] 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_abs_structure_details 
;
 Flack x determined using 1553 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4862
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
Br Br 0.60571(3) 0.61991(8) 0.71444(2) 0.04615(13) Uani 1 1 d . . . . .
O1 O -0.0810(3) 0.8760(4) 0.29850(19) 0.0401(7) Uani 1 1 d . . . . .
O2 O 0.1058(4) 0.2555(7) 0.1528(2) 0.0720(11) Uani 1 1 d . . . . .
O3 O 0.1469(5) 0.5529(8) 0.0803(3) 0.1001(18) Uani 1 1 d . . . . .
N N -0.0327(4) 0.3948(6) 0.2796(3) 0.0412(9) Uani 1 1 d . . . . .
C1 C 0.0971(4) 0.5037(6) 0.3023(3) 0.0365(8) Uani 1 1 d . . . . .
C2 C 0.1165(3) 0.6652(5) 0.3788(2) 0.0295(8) Uani 1 1 d . . . . .
C3 C 0.0282(4) 0.8373(6) 0.3739(2) 0.0308(7) Uani 1 1 d . . . . .
C4 C 0.0474(4) 1.0011(6) 0.4399(2) 0.0339(8) Uani 1 1 d . . . . .
H4 H -0.0145 1.1155 0.4336 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1574(4) 0.9915(6) 0.5134(2) 0.0337(8) Uani 1 1 d . . . . .
H5 H 0.1711 1.1018 0.5566 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2507(4) 0.8158(6) 0.5249(2) 0.0314(8) Uani 1 1 d . . . . .
C7 C 0.3635(4) 0.8040(7) 0.6016(2) 0.0340(8) Uani 1 1 d . . . . .
H7 H 0.3777 0.9137 0.6450 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4515(3) 0.6327(9) 0.6122(2) 0.0355(7) Uani 1 1 d . . . . .
C9 C 0.4330(4) 0.4643(7) 0.5480(3) 0.0391(9) Uani 1 1 d . . . . .
H9 H 0.4937 0.3474 0.5567 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3255(4) 0.4729(7) 0.4728(3) 0.0363(8) Uani 1 1 d . . . . .
H10 H 0.3145 0.3613 0.4304 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2300(3) 0.6480(7) 0.4576(2) 0.0296(7) Uani 1 1 d . . . . .
C12 C -0.1559(5) 0.5017(7) 0.2448(3) 0.0341(9) Uani 1 1 d . . . . .
C13 C -0.2644(4) 0.3784(7) 0.1931(3) 0.0435(10) Uani 1 1 d . . . . .
H13 H -0.2495 0.2343 0.1771 0.052 Uiso 1 1 calc R U . . .
C14 C -0.3916(5) 0.4616(8) 0.1652(3) 0.0535(12) Uani 1 1 d . . . . .
H14 H -0.4616 0.3742 0.1308 0.064 Uiso 1 1 calc R U . . .
C15 C -0.4176(4) 0.6755(7) 0.1877(3) 0.0494(12) Uani 1 1 d . . . . .
H15 H -0.5047 0.7314 0.1706 0.059 Uiso 1 1 calc R U . . .
C16 C -0.3105(4) 0.8039(7) 0.2365(3) 0.0400(9) Uani 1 1 d . . . . .
H16 H -0.3260 0.9478 0.2523 0.048 Uiso 1 1 calc R U . . .
C17 C -0.1803(4) 0.7209(7) 0.2619(3) 0.0322(9) Uani 1 1 d . . . . .
C18 C 0.1269(4) 0.6173(13) 0.2226(2) 0.0473(8) Uani 1 1 d . . . . .
H18A H 0.0608 0.7325 0.1991 0.057 Uiso 1 1 calc R U . . .
H18B H 0.2148 0.6865 0.2424 0.057 Uiso 1 1 calc R U . . .
C19 C 0.1233(5) 0.4506(10) 0.1494(3) 0.0593(13) Uani 1 1 d . . . . .
C20 C 0.1372(9) 0.4202(19) 0.0007(5) 0.137(4) Uani 1 1 d . . . . .
H20A H 0.0886 0.2845 0.0033 0.164 Uiso 1 1 calc R U . . .
H20B H 0.0864 0.5022 -0.0517 0.164 Uiso 1 1 calc R U . . .
C21 C 0.2541(9) 0.370(3) -0.0071(7) 0.207(7) Uani 1 1 d . . . . .
H21A H 0.2426 0.2841 -0.0601 0.249 Uiso 1 1 calc R U . . .
H21B H 0.3041 0.2863 0.0439 0.249 Uiso 1 1 calc R U . . .
H21C H 0.3020 0.5042 -0.0108 0.249 Uiso 1 1 calc R U . . .
H1N H -0.034(4) 0.281(7) 0.256(3) 0.026(10) Uiso 1 1 d . . . . .
H1 H 0.163(4) 0.396(6) 0.320(2) 0.024(9) 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
Br C8 1.903(3) . ?
O1 C17 1.386(5) . ?
O1 C3 1.395(4) . ?
O2 C19 1.194(7) . ?
O3 C19 1.336(7) . ?
O3 C20 1.463(7) . ?
N C12 1.395(6) . ?
N C1 1.450(5) . ?
N H1N 0.78(4) . ?
C1 C2 1.513(5) . ?
C1 C18 1.540(7) . ?
C1 H1 0.93(4) . ?
C2 C3 1.374(5) . ?
C2 C11 1.437(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.363(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(5) . ?
C6 C11 1.433(5) . ?
C7 C8 1.358(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.404(6) . ?
C9 C10 1.364(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.422(5) . ?
C10 H10 0.9300 . ?
C12 C17 1.388(5) . ?
C12 C13 1.394(6) . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(6) . ?
C16 H16 0.9300 . ?
C18 C19 1.520(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C20 C21 1.297(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C17 O1 C3 123.9(3) . . ?
C19 O3 C20 117.5(6) . . ?
C12 N C1 124.7(3) . . ?
C12 N H1N 110(3) . . ?
C1 N H1N 113(3) . . ?
N C1 C2 112.2(3) . . ?
N C1 C18 113.8(3) . . ?
C2 C1 C18 110.5(4) . . ?
N C1 H1 108(2) . . ?
C2 C1 H1 108(2) . . ?
C18 C1 H1 104(2) . . ?
C3 C2 C11 117.8(3) . . ?
C3 C2 C1 121.0(3) . . ?
C11 C2 C1 121.1(3) . . ?
C2 C3 O1 122.4(3) . . ?
C2 C3 C4 123.1(3) . . ?
O1 C3 C4 114.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 C11 119.8(3) . . ?
C5 C6 C11 119.3(3) . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 Br 120.2(3) . . ?
C9 C8 Br 118.5(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 117.2(3) . . ?
C10 C11 C2 123.6(3) . . ?
C6 C11 C2 119.2(3) . . ?
C17 C12 N 124.5(5) . . ?
C17 C12 C13 117.2(5) . . ?
N C12 C13 118.3(4) . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 120.9(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
O1 C17 C12 124.4(4) . . ?
O1 C17 C16 114.9(4) . . ?
C12 C17 C16 120.6(4) . . ?
C19 C18 C1 111.0(6) . . ?
C19 C18 H18A 109.4 . . ?
C1 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C1 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
O2 C19 O3 124.0(5) . . ?
O2 C19 C18 125.9(5) . . ?
O3 C19 C18 110.0(5) . . ?
C21 C20 O3 112.5(8) . . ?
C21 C20 H20A 109.1 . . ?
O3 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
O3 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-1



