# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_JN181
_database_code_depnum_ccdc_archive 'CCDC 1998235'
loop_
_audit_author_name
_audit_author_address
'Eduardo C Escudero Adan'
;ICIQ Tarragona
Spain
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.32

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/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                   6.2396(2)
_cell_length_b                   23.7102(7)
_cell_length_c                   9.2667(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.545(3)
_cell_angle_gamma                90
_cell_volume                     1362.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7760
_cell_measurement_theta_min      2.7680
_cell_measurement_theta_max      29.3550

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            12489
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3456
_reflns_number_gt                3098
_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       
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_cell_refinement       
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_reduction        
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_structure_solution    Sir2019
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0567P)²+0.3991P] 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         3456
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.54713(15) 0.67425(4) 0.15786(10) 0.01519(19) Uani 1 1 d . . . . .
N1 N 0.61044(13) 0.67103(3) 0.31138(9) 0.01646(18) Uani 1 1 d . . . . .
O1 O 0.92311(12) 0.71852(3) 0.29362(8) 0.02152(17) Uani 1 1 d . . . . .
C2 C 0.34189(16) 0.69325(4) 0.10484(11) 0.0188(2) Uani 1 1 d . . . . .
H2 H 0.243445 0.704629 0.170259 0.023 Uiso 1 1 calc R U . . .
C3 C 0.28152(17) 0.69550(4) -0.04466(12) 0.0218(2) Uani 1 1 d . . . . .
H3 H 0.140977 0.708022 -0.080833 0.026 Uiso 1 1 calc R U . . .
C4 C 0.42533(18) 0.67958(4) -0.14097(11) 0.0231(2) Uani 1 1 d . . . . .
H4 H 0.383875 0.681349 -0.242744 0.028 Uiso 1 1 calc R U . . .
C5 C 0.63039(17) 0.66104(4) -0.08746(11) 0.0216(2) Uani 1 1 d . . . . .
H5 H 0.729419 0.650213 -0.153029 0.026 Uiso 1 1 calc R U . . .
C6 C 0.69147(16) 0.65825(4) 0.06122(11) 0.0177(2) Uani 1 1 d . . . . .
H6 H 0.831737 0.645421 0.097052 0.021 Uiso 1 1 calc R U . . .
C7 C 0.79904(16) 0.69578(4) 0.36937(11) 0.0167(2) Uani 1 1 d . . . . .
C8 C 0.85234(17) 0.69135(4) 0.53191(11) 0.0193(2) Uani 1 1 d . . . . .
H8A H 0.726046 0.703412 0.579857 0.023 Uiso 1 1 calc R U . . .
H8B H 0.973813 0.716944 0.564059 0.023 Uiso 1 1 calc R U . . .
C9 C 0.91362(16) 0.63087(4) 0.57790(11) 0.0187(2) Uani 1 1 d . . . . .
H9A H 1.013669 0.615852 0.511701 0.022 Uiso 1 1 calc R U . . .
H9B H 0.992093 0.631763 0.676943 0.022 Uiso 1 1 calc R U . . .
C10 C 0.72440(15) 0.59087(4) 0.57739(10) 0.01606(19) Uani 1 1 d . . . . .
C11 C 0.53144(15) 0.59947(4) 0.50198(10) 0.0173(2) Uani 1 1 d . . . . .
H11 H 0.427750 0.570659 0.510344 0.021 Uiso 1 1 calc R U . . .
C12 C 0.45469(15) 0.64857(4) 0.40517(11) 0.0185(2) Uani 1 1 d . . . . .
H12A H 0.323522 0.636626 0.342368 0.022 Uiso 1 1 calc R U . . .
H12B H 0.412435 0.679605 0.467559 0.022 Uiso 1 1 calc R U . . .
C13 C 0.76530(16) 0.54029(4) 0.67233(10) 0.0169(2) Uani 1 1 d . . . . .
C14 C 0.96556(17) 0.51300(4) 0.68437(12) 0.0228(2) Uani 1 1 d . . . . .
H14 H 1.073863 0.525958 0.628173 0.027 Uiso 1 1 calc R U . . .
C15 C 1.00878(18) 0.46729(5) 0.77710(13) 0.0270(2) Uani 1 1 d . . . . .
H15 H 1.144827 0.448937 0.782790 0.032 Uiso 1 1 calc R U . . .
C16 C 0.85280(19) 0.44847(4) 0.86141(13) 0.0259(2) Uani 1 1 d . . . . .
H16 H 0.882827 0.417753 0.926403 0.031 Uiso 1 1 calc R U . . .
C17 C 0.65307(18) 0.47475(4) 0.85021(12) 0.0238(2) Uani 1 1 d . . . . .
H17 H 0.545426 0.461551 0.906642 0.029 Uiso 1 1 calc R U . . .
C18 C 0.60924(17) 0.52030(4) 0.75694(12) 0.0203(2) Uani 1 1 d . . . . .
H00A H 0.471973 0.538045 0.750552 0.024 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
C1 C2 1.3932(13) . ?
C1 C6 1.3932(13) . ?
C1 N1 1.4345(12) . ?
N1 C7 1.3690(12) . ?
N1 C12 1.4751(12) . ?
O1 C7 1.2274(12) . ?
C2 C3 1.3946(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3881(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3898(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3886(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5087(13) . ?
C8 C9 1.5319(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5140(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3370(14) . ?
C10 C13 1.4921(13) . ?
C11 C12 1.5138(13) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4002(14) . ?
C13 C18 1.4006(13) . ?
C14 C15 1.3903(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3893(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3866(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3909(14) . ?
C17 H17 0.9500 . ?
C18 H00A 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
C2 C1 C6 119.80(9) . . ?
C2 C1 N1 120.34(8) . . ?
C6 C1 N1 119.86(8) . . ?
C7 N1 C1 119.58(8) . . ?
C7 N1 C12 121.21(8) . . ?
C1 N1 C12 118.56(8) . . ?
C1 C2 C3 119.74(9) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.47(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.53(10) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.43(9) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.03(9) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N1 122.27(9) . . ?
O1 C7 C8 121.33(9) . . ?
N1 C7 C8 116.34(8) . . ?
C7 C8 C9 111.26(8) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 114.56(8) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C13 120.93(9) . . ?
C11 C10 C9 124.17(9) . . ?
C13 C10 C9 114.88(8) . . ?
C10 C11 C12 129.21(9) . . ?
C10 C11 H11 115.4 . . ?
C12 C11 H11 115.4 . . ?
N1 C12 C11 116.21(8) . . ?
N1 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
N1 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C18 118.04(9) . . ?
C14 C13 C10 120.63(9) . . ?
C18 C13 C10 121.26(9) . . ?
C15 C14 C13 121.20(10) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C16 C15 C14 119.93(10) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.66(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.45(10) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.71(10) . . ?
C17 C18 H00A 119.6 . . ?
C13 C18 H00A 119.6 . . ?

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
C2 C1 N1 C7 -128.28(10) . . . . ?
C6 C1 N1 C7 51.80(12) . . . . ?
C2 C1 N1 C12 42.61(12) . . . . ?
C6 C1 N1 C12 -137.32(9) . . . . ?
C6 C1 C2 C3 0.73(14) . . . . ?
N1 C1 C2 C3 -179.20(9) . . . . ?
C1 C2 C3 C4 -0.76(15) . . . . ?
C2 C3 C4 C5 0.31(16) . . . . ?
C3 C4 C5 C6 0.18(15) . . . . ?
C4 C5 C6 C1 -0.20(15) . . . . ?
C2 C1 C6 C5 -0.26(14) . . . . ?
N1 C1 C6 C5 179.67(8) . . . . ?
C1 N1 C7 O1 -3.73(14) . . . . ?
C12 N1 C7 O1 -174.37(9) . . . . ?
C1 N1 C7 C8 179.02(8) . . . . ?
C12 N1 C7 C8 8.38(13) . . . . ?
O1 C7 C8 C9 -106.64(10) . . . . ?
N1 C7 C8 C9 70.63(11) . . . . ?
C7 C8 C9 C10 -76.82(10) . . . . ?
C8 C9 C10 C11 20.94(13) . . . . ?
C8 C9 C10 C13 -157.45(8) . . . . ?
C13 C10 C11 C12 177.38(9) . . . . ?
C9 C10 C11 C12 -0.92(16) . . . . ?
C7 N1 C12 C11 -64.41(12) . . . . ?
C1 N1 C12 C11 124.86(9) . . . . ?
C10 C11 C12 N1 40.24(14) . . . . ?
C11 C10 C13 C14 143.38(10) . . . . ?
C9 C10 C13 C14 -38.17(13) . . . . ?
C11 C10 C13 C18 -39.64(14) . . . . ?
C9 C10 C13 C18 138.82(10) . . . . ?
C18 C13 C14 C15 0.19(16) . . . . ?
C10 C13 C14 C15 177.27(10) . . . . ?
C13 C14 C15 C16 -0.94(18) . . . . ?
C14 C15 C16 C17 1.33(18) . . . . ?
C15 C16 C17 C18 -1.00(17) . . . . ?
C16 C17 C18 C13 0.26(17) . . . . ?
C14 C13 C18 C17 0.14(15) . . . . ?
C10 C13 C18 C17 -176.91(9) . . . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_mo_JN236_0m
_database_code_depnum_ccdc_archive 'CCDC 2001102'
loop_
_audit_author_name
_audit_author_address
'Eduardo C Escudero Adan'
;ICIQ Tarragona
Spain
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Br2 N O'
_chemical_formula_weight         423.14

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                   13.0644(10)
_cell_length_b                   7.0550(6)
_cell_length_c                   17.3068(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.551(2)
_cell_angle_gamma                90
_cell_volume                     1590.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4538
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      29.70

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    5.099
_shelx_estimated_absorpt_T_min   0.166
_shelx_estimated_absorpt_T_max   0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1854
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            13440
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4162
_reflns_number_gt                3363
_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 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0425P)²+0.0939P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4162
_refine_ls_number_parameters     200
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.045
_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
Br1 Br 0.81796(2) 0.30653(4) 0.52992(2) 0.01197(10) Uani 1 1 d . . . . .
N1 N 0.74091(18) 0.7909(3) 0.39364(15) 0.0084(5) Uani 1 1 d . . . . .
O1 O 0.87103(15) 1.0031(3) 0.40466(13) 0.0140(5) Uani 1 1 d . . . . .
C1 C 0.7456(2) 0.5464(4) 0.55703(17) 0.0081(5) Uani 1 1 d . . . . .
C2 C 0.6629(2) 0.5746(4) 0.49037(17) 0.0072(5) Uani 1 1 d . . . . .
H2 H 0.618839 0.458598 0.488169 0.009 Uiso 1 1 calc R U . . .
Br2 Br 0.57493(2) 0.78922(4) 0.51672(2) 0.01136(10) Uani 1 1 d . . . . .
C3 C 0.6986(2) 0.6037(4) 0.40941(17) 0.0091(6) Uani 1 1 d . . . . .
H3A H 0.751531 0.507191 0.400823 0.011 Uiso 1 1 calc R U . . .
H3AB H 0.639601 0.579863 0.371133 0.011 Uiso 1 1 calc R U . . .
C4 C 0.8325(2) 0.8564(4) 0.42635(18) 0.0091(6) Uani 1 1 d . . . . .
C6 C 0.8265(2) 0.7024(4) 0.56282(18) 0.0097(6) Uani 1 1 d . . . . .
H6A H 0.876895 0.671710 0.606789 0.012 Uiso 1 1 calc R U . . .
H6AB H 0.792249 0.822072 0.575921 0.012 Uiso 1 1 calc R U . . .
C5 C 0.8862(2) 0.7394(4) 0.49122(17) 0.0107(6) Uani 1 1 d . . . . .
H5A H 0.951238 0.803983 0.508678 0.013 Uiso 1 1 calc R U . . .
H5AB H 0.904446 0.615247 0.469425 0.013 Uiso 1 1 calc R U . . .
C9 C 0.6117(2) 0.9159(4) 0.20079(18) 0.0120(6) Uani 1 1 d . . . . .
H9 H 0.600622 0.862774 0.150390 0.014 Uiso 1 1 calc R U . . .
C8 C 0.6710(2) 0.8193(4) 0.25846(18) 0.0104(6) Uani 1 1 d . . . . .
H8 H 0.700786 0.700437 0.247440 0.013 Uiso 1 1 calc R U . . .
C7 C 0.6866(2) 0.8973(4) 0.33224(17) 0.0086(6) Uani 1 1 d . . . . .
C10 C 0.5690(2) 1.0898(4) 0.21703(18) 0.0142(6) Uani 1 1 d . . . . .
H10 H 0.528289 1.155537 0.177732 0.017 Uiso 1 1 calc R U . . .
C11 C 0.5854(2) 1.1682(4) 0.2905(2) 0.0145(6) Uani 1 1 d . . . . .
H11 H 0.556504 1.288072 0.301228 0.017 Uiso 1 1 calc R U . . .
C12 C 0.6439(2) 1.0719(4) 0.34863(18) 0.0115(6) Uani 1 1 d . . . . .
H12 H 0.654614 1.124911 0.399079 0.014 Uiso 1 1 calc R U . . .
C13 C 0.6951(2) 0.5063(4) 0.63188(17) 0.0084(5) Uani 1 1 d . U . . .
C14 C 0.7039(2) 0.6294(4) 0.69467(18) 0.0117(6) Uani 1 1 d . U . . .
H14 H 0.748683 0.735409 0.693793 0.014 Uiso 1 1 calc R U . . .
C15 C 0.6482(2) 0.5998(4) 0.75879(18) 0.0140(6) Uani 1 1 d . U . . .
H15 H 0.655857 0.684508 0.801532 0.017 Uiso 1 1 calc R U . . .
C16 C 0.5815(2) 0.4472(4) 0.76069(18) 0.0141(6) Uani 1 1 d . U . . .
H16 H 0.541452 0.429852 0.803640 0.017 Uiso 1 1 calc R U . . .
C17 C 0.5737(2) 0.3203(4) 0.69941(19) 0.0135(6) Uani 1 1 d . U . . .
H17 H 0.529607 0.213509 0.700780 0.016 Uiso 1 1 calc R U . . .
C18 C 0.6305(2) 0.3495(4) 0.63606(18) 0.0112(6) Uani 1 1 d . U . . .
H18 H 0.625319 0.260881 0.594603 0.013 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
Br1 C1 2.011(3) . ?
N1 C4 1.363(4) . ?
N1 C7 1.441(4) . ?
N1 C3 1.466(3) . ?
O1 C4 1.223(3) . ?
C1 C6 1.524(4) . ?
C1 C13 1.527(4) . ?
C1 C2 1.530(4) . ?
C2 C3 1.525(4) . ?
C2 Br2 1.976(3) . ?
C4 C5 1.519(4) . ?
C6 C5 1.538(4) . ?
C9 C10 1.386(4) . ?
C9 C8 1.392(4) . ?
C8 C7 1.390(4) . ?
C7 C12 1.391(4) . ?
C10 C11 1.388(5) . ?
C11 C12 1.391(4) . ?
C13 C14 1.389(4) . ?
C13 C18 1.397(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.387(4) . ?

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
C4 N1 C7 119.7(2) . . ?
C4 N1 C3 124.0(2) . . ?
C7 N1 C3 115.8(2) . . ?
C6 C1 C13 115.0(2) . . ?
C6 C1 C2 113.6(2) . . ?
C13 C1 C2 109.7(2) . . ?
C6 C1 Br1 106.69(18) . . ?
C13 C1 Br1 106.56(18) . . ?
C2 C1 Br1 104.52(18) . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 Br2 109.57(18) . . ?
C1 C2 Br2 108.36(18) . . ?
N1 C3 C2 116.1(2) . . ?
O1 C4 N1 121.9(3) . . ?
O1 C4 C5 120.6(2) . . ?
N1 C4 C5 117.5(2) . . ?
C1 C6 C5 117.6(2) . . ?
C4 C5 C6 117.0(2) . . ?
C10 C9 C8 119.9(3) . . ?
C7 C8 C9 119.8(3) . . ?
C8 C7 C12 120.4(3) . . ?
C8 C7 N1 119.9(2) . . ?
C12 C7 N1 119.5(3) . . ?
C9 C10 C11 120.2(3) . . ?
C10 C11 C12 120.2(3) . . ?
C7 C12 C11 119.4(3) . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C1 122.2(2) . . ?
C18 C13 C1 119.6(3) . . ?
C13 C14 C15 120.9(3) . . ?
C16 C15 C14 120.4(3) . . ?
C17 C16 C15 119.4(3) . . ?
C16 C17 C18 119.9(3) . . ?
C17 C18 C13 121.4(3) . . ?

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 53.7(3) . . . . ?
C13 C1 C2 C3 -176.1(2) . . . . ?
Br1 C1 C2 C3 -62.2(3) . . . . ?
C6 C1 C2 Br2 -71.1(3) . . . . ?
C13 C1 C2 Br2 59.1(2) . . . . ?
Br1 C1 C2 Br2 173.01(11) . . . . ?
C4 N1 C3 C2 69.6(4) . . . . ?
C7 N1 C3 C2 -118.6(3) . . . . ?
C1 C2 C3 N1 -75.5(3) . . . . ?
Br2 C2 C3 N1 48.6(3) . . . . ?
C7 N1 C4 O1 -0.6(4) . . . . ?
C3 N1 C4 O1 170.8(3) . . . . ?
C7 N1 C4 C5 179.6(2) . . . . ?
C3 N1 C4 C5 -8.9(4) . . . . ?
C13 C1 C6 C5 175.4(2) . . . . ?
C2 C1 C6 C5 -57.1(3) . . . . ?
Br1 C1 C6 C5 57.5(3) . . . . ?
O1 C4 C5 C6 122.0(3) . . . . ?
N1 C4 C5 C6 -58.2(4) . . . . ?
C1 C6 C5 C4 79.6(3) . . . . ?
C10 C9 C8 C7 0.4(4) . . . . ?
C9 C8 C7 C12 -0.5(4) . . . . ?
C9 C8 C7 N1 175.0(2) . . . . ?
C4 N1 C7 C8 115.8(3) . . . . ?
C3 N1 C7 C8 -56.3(3) . . . . ?
C4 N1 C7 C12 -68.6(3) . . . . ?
C3 N1 C7 C12 119.2(3) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C8 C7 C12 C11 0.0(4) . . . . ?
N1 C7 C12 C11 -175.5(2) . . . . ?
C10 C11 C12 C7 0.6(4) . . . . ?
C6 C1 C13 C14 14.3(4) . . . . ?
C2 C1 C13 C14 -115.2(3) . . . . ?
Br1 C1 C13 C14 132.2(2) . . . . ?
C6 C1 C13 C18 -171.2(2) . . . . ?
C2 C1 C13 C18 59.3(3) . . . . ?
Br1 C1 C13 C18 -53.3(3) . . . . ?
C18 C13 C14 C15 -1.6(4) . . . . ?
C1 C13 C14 C15 173.0(3) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C17 2.5(4) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C14 C13 C18 C17 2.4(4) . . . . ?
C1 C13 C18 C17 -172.4(3) . . . . ?

_refine_diff_density_max         1.290
_refine_diff_density_min         -1.273
_refine_diff_density_rms         0.149

