# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_MX52_21
_database_code_depnum_ccdc_archive 'CCDC 2251735'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2023-06-19 deposited with the CCDC.	2023-11-09 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         'C23 H23 N3 O'
_chemical_formula_sum            'C23 H23 N3 O'
_chemical_formula_weight         357.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.23070(10)
_cell_length_b                   16.7632(3)
_cell_length_c                   21.3103(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.56(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8239
_cell_measurement_theta_min      4.1650
_cell_measurement_theta_max      76.8870

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.69132
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19367
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.149
_diffrn_reflns_theta_max         77.673
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3929
_reflns_number_gt                3694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    1.000

_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0591P)²+0.1892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.3646(3) 0.87385(8) 0.00003(6) 0.0278(3) Uani 1 1 d . . . . .
N1 N -0.2025(3) 1.15761(9) -0.00750(8) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.2693(3) 1.01250(9) -0.04073(7) 0.0219(3) Uani 1 1 d . . . . .
N3 N 0.4491(3) 1.01133(9) -0.08175(7) 0.0216(3) Uani 1 1 d . . . . .
C1 C -0.0813(3) 1.08680(11) 0.00271(9) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.1214(4) 1.08064(11) -0.03916(9) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.1208(3) 1.15153(10) -0.07807(9) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.2632(4) 1.17808(11) -0.12948(9) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.404242 1.147703 -0.144255 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1971(4) 1.24951(11) -0.15897(9) 0.0253(4) Uani 1 1 d . . . . .
C6 C -0.0093(4) 1.29442(11) -0.13600(10) 0.0260(4) Uani 1 1 d . . . . .
H6 H -0.050655 1.343406 -0.155989 0.031 Uiso 1 1 calc R U . . .
C7 C -0.1553(4) 1.26974(11) -0.08503(9) 0.0248(4) Uani 1 1 d . . . . .
H7 H -0.295183 1.300531 -0.070120 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0871(3) 1.19761(11) -0.05673(9) 0.0226(4) Uani 1 1 d . . . . .
C9 C 0.5898(3) 0.94011(10) -0.08354(9) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.5451(4) 0.87409(11) -0.04498(9) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.6940(4) 0.80392(11) -0.05148(10) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.660322 0.759115 -0.025454 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8852(4) 0.80038(11) -0.09487(10) 0.0285(4) Uani 1 1 d . . . . .
H12 H 0.982890 0.752862 -0.098695 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9414(4) 0.86633(11) -0.13454(9) 0.0249(4) Uani 1 1 d . . . . .
C14 C 1.1425(4) 0.86346(12) -0.17859(9) 0.0288(4) Uani 1 1 d . . . . .
H14 H 1.242685 0.816403 -0.182193 0.035 Uiso 1 1 calc R U . . .
C15 C 1.1955(4) 0.92786(13) -0.21638(10) 0.0300(4) Uani 1 1 d . . . . .
H15 H 1.331297 0.925251 -0.245920 0.036 Uiso 1 1 calc R U . . .
C16 C 1.0480(4) 0.99742(13) -0.21109(9) 0.0287(4) Uani 1 1 d . . . . .
H16 H 1.086362 1.042115 -0.236836 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8491(4) 1.00181(12) -0.16922(9) 0.0256(4) Uani 1 1 d . . . . .
H17 H 0.749051 1.049033 -0.167004 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7913(4) 0.93682(11) -0.12937(9) 0.0231(4) Uani 1 1 d . . . . .
C19 C -0.1713(4) 1.02871(12) 0.05075(9) 0.0267(4) Uani 1 1 d . . . . .
H19A H -0.173012 0.974837 0.031725 0.032 Uiso 1 1 calc R U . . .
H19B H -0.349541 1.042218 0.062207 0.032 Uiso 1 1 calc R U . . .
C20 C -0.0114(4) 1.02575(12) 0.11059(10) 0.0324(5) Uani 1 1 d . . . . .
H20A H -0.011584 1.079133 0.130460 0.039 Uiso 1 1 calc R U . . .
H20B H 0.167419 1.012381 0.099599 0.039 Uiso 1 1 calc R U . . .
C21 C -0.1119(5) 0.96447(14) 0.15751(10) 0.0400(5) Uani 1 1 d . . . . .
H21A H -0.013687 0.969626 0.197022 0.048 Uiso 1 1 calc R U . . .
H21B H -0.292648 0.977055 0.167052 0.048 Uiso 1 1 calc R U . . .
C22 C -0.0959(11) 0.87978(17) 0.13555(16) 0.0813(13) Uani 1 1 d . . . . .
H22A H -0.200316 0.873158 0.097731 0.122 Uiso 1 1 calc R U . . .
H22B H -0.159202 0.844223 0.168581 0.122 Uiso 1 1 calc R U . . .
H22C H 0.082381 0.866522 0.125970 0.122 Uiso 1 1 calc R U . . .
C24 C 0.3424(4) 1.27672(13) -0.21618(10) 0.0328(4) Uani 1 1 d . . . . .
H24A H 0.526430 1.272146 -0.208302 0.049 Uiso 1 1 calc R U . . .
H24B H 0.299531 1.332432 -0.225300 0.049 Uiso 1 1 calc R U . . .
H24C H 0.295820 1.243264 -0.252112 0.049 Uiso 1 1 calc R U . . .
H1N H -0.337(5) 1.1750(16) 0.0138(12) 0.031(6) Uiso 1 1 d . . . . .
H1 H 0.272(6) 0.922(2) -0.0029(16) 0.058(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
O1 C10 1.346(2) . ?
N1 C1 1.363(2) . ?
N1 C8 1.384(3) . ?
N2 N3 1.284(2) . ?
N2 C2 1.380(2) . ?
N3 C9 1.403(2) . ?
C1 C2 1.390(3) . ?
C1 C19 1.489(3) . ?
C2 C3 1.449(3) . ?
C3 C4 1.398(3) . ?
C3 C8 1.409(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.404(3) . ?
C5 C24 1.507(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.397(3) . ?
C9 C10 1.398(3) . ?
C9 C18 1.438(3) . ?
C10 C11 1.417(3) . ?
C11 C12 1.363(3) . ?
C12 C13 1.422(3) . ?
C13 C14 1.411(3) . ?
C13 C18 1.423(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.373(3) . ?
C17 C18 1.414(3) . ?
C19 C20 1.526(3) . ?
C20 C21 1.527(3) . ?
C21 C22 1.497(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
C1 N1 C8 109.88(16) . . ?
N3 N2 C2 116.07(15) . . ?
N2 N3 C9 114.55(15) . . ?
N1 C1 C2 108.49(16) . . ?
N1 C1 C19 122.13(17) . . ?
C2 C1 C19 129.35(17) . . ?
N2 C2 C1 120.31(16) . . ?
N2 C2 C3 131.79(17) . . ?
C1 C2 C3 107.74(15) . . ?
C4 C3 C8 119.32(17) . . ?
C4 C3 C2 135.11(17) . . ?
C8 C3 C2 105.47(16) . . ?
C5 C4 C3 119.60(18) . . ?
C4 C5 C6 119.57(18) . . ?
C4 C5 C24 119.91(18) . . ?
C6 C5 C24 120.50(17) . . ?
C7 C6 C5 122.34(17) . . ?
C6 C7 C8 117.01(18) . . ?
N1 C8 C7 129.43(17) . . ?
N1 C8 C3 108.40(16) . . ?
C7 C8 C3 122.14(18) . . ?
C10 C9 N3 124.76(17) . . ?
C10 C9 C18 119.42(16) . . ?
N3 C9 C18 115.82(15) . . ?
O1 C10 C9 122.57(16) . . ?
O1 C10 C11 116.90(17) . . ?
C9 C10 C11 120.52(17) . . ?
C12 C11 C10 120.34(18) . . ?
C11 C12 C13 121.40(18) . . ?
C14 C13 C12 121.54(18) . . ?
C14 C13 C18 119.43(18) . . ?
C12 C13 C18 119.03(18) . . ?
C15 C14 C13 120.88(18) . . ?
C14 C15 C16 119.65(19) . . ?
C17 C16 C15 120.91(19) . . ?
C16 C17 C18 120.74(18) . . ?
C17 C18 C13 118.38(17) . . ?
C17 C18 C9 122.34(16) . . ?
C13 C18 C9 119.27(17) . . ?
C1 C19 C20 114.99(16) . . ?
C19 C20 C21 112.37(17) . . ?
C22 C21 C20 114.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N2 0.95(4) 1.71(3) 2.531(2) 142(3) . yes

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_MX51_21_a
_database_code_depnum_ccdc_archive 'CCDC 2251736'
loop_
_audit_author_name
_audit_author_address
'Craig Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2023-06-19 deposited with the CCDC.	2023-11-09 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         'C18 H12 Br N3 O'
_chemical_formula_sum            'C18 H12 Br N3 O'
_chemical_formula_weight         366.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   10.8851(2)
_cell_length_b                   33.8049(6)
_cell_length_c                   3.95730(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1456.17(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8228
_cell_measurement_theta_min      4.2460
_cell_measurement_theta_max      76.9790

_exptl_crystal_description       plate
_exptl_crystal_colour            red-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    3.914
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.50578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14749
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         4.267
_diffrn_reflns_theta_max         77.682
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.808
_diffrn_reflns_point_group_measured_fraction_full 0.848
_reflns_number_total             2486
_reflns_number_gt                2375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.417
_reflns_Friedel_fraction_max     0.560
_reflns_Friedel_fraction_full    0.641

_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0615P)²+0.7065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 657 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2486
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.003
_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 0.29468(3) 0.55302(2) 1.0672(2) 0.02772(16) Uani 1 1 d . . . . .
O1 O 0.0715(3) 0.32112(8) 0.8312(9) 0.0274(7) Uani 1 1 d . . . . .
N1 N 0.4771(3) 0.24861(10) 0.1864(10) 0.0236(8) Uani 1 1 d . . . . .
N2 N 0.2829(3) 0.32051(9) 0.5620(14) 0.0203(6) Uani 1 1 d . . . . .
N3 N 0.2997(3) 0.35753(9) 0.6048(12) 0.0197(7) Uani 1 1 d . . . . .
C1 C 0.3747(4) 0.26046(12) 0.3530(11) 0.0222(8) Uani 1 1 d . . . . .
H1 H 0.311444 0.243402 0.431411 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3761(4) 0.30101(11) 0.3915(11) 0.0205(8) Uani 1 1 d . . . . .
C3 C 0.4877(3) 0.31530(11) 0.2380(11) 0.0198(8) Uani 1 1 d . . . . .
C4 C 0.5431(4) 0.35250(12) 0.1911(12) 0.0234(9) Uani 1 1 d . . . . .
H4 H 0.504794 0.375892 0.272363 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6545(4) 0.35422(11) 0.0241(13) 0.0242(9) Uani 1 1 d . . . . .
H5 H 0.693004 0.379177 -0.006584 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7125(4) 0.32005(14) -0.1018(13) 0.0258(10) Uani 1 1 d . . . . .
H6 H 0.789237 0.322222 -0.214413 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6583(4) 0.28332(12) -0.0626(12) 0.0249(9) Uani 1 1 d . . . . .
H7 H 0.695776 0.260087 -0.149937 0.030 Uiso 1 1 calc R U . . .
C8 C 0.5476(3) 0.28163(10) 0.1084(12) 0.0206(8) Uani 1 1 d . . . . .
C9 C 0.2056(3) 0.37736(12) 0.7794(12) 0.0196(9) Uani 1 1 d . . . . .
C10 C 0.0958(4) 0.36006(12) 0.8849(12) 0.0241(9) Uani 1 1 d . . . . .
C11 C 0.0057(3) 0.38288(11) 1.0539(16) 0.0252(8) Uani 1 1 d . . . . .
H11 H -0.067449 0.370612 1.132307 0.030 Uiso 1 1 calc R U . . .
C12 C 0.0233(3) 0.42231(11) 1.1046(14) 0.0251(8) Uani 1 1 d . . . . .
H12 H -0.039704 0.437462 1.208554 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1344(4) 0.44129(11) 1.0051(11) 0.0215(9) Uani 1 1 d . . . . .
C14 C 0.1545(3) 0.48198(10) 1.0663(15) 0.0225(7) Uani 1 1 d . . . . .
H14 H 0.092912 0.497481 1.173159 0.027 Uiso 1 1 calc R U . . .
C15 C 0.2632(4) 0.49885(12) 0.9705(11) 0.0235(9) Uani 1 1 d . . . . .
C16 C 0.3560(4) 0.47679(12) 0.8079(12) 0.0224(8) Uani 1 1 d . . . . .
H16 H 0.430650 0.489149 0.742015 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3376(4) 0.43768(12) 0.7465(11) 0.0218(8) Uani 1 1 d . . . . .
H17 H 0.400324 0.422853 0.637850 0.026 Uiso 1 1 calc R U . . .
C18 C 0.2272(4) 0.41850(12) 0.8407(11) 0.0189(8) Uani 1 1 d . . . . .
H1N H 0.496(5) 0.2224(16) 0.125(18) 0.048(17) Uiso 1 1 d . . . . .
H1A H 0.135(7) 0.3141(19) 0.71(2) 0.06(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.902(4) . ?
O1 C10 1.360(5) . ?
N1 C1 1.356(5) . ?
N1 C8 1.389(5) . ?
N2 N3 1.276(4) . ?
N2 C2 1.385(5) . ?
N3 C9 1.406(5) . ?
C1 C2 1.379(5) . ?
C2 C3 1.441(5) . ?
C3 C4 1.407(5) . ?
C3 C8 1.409(5) . ?
C4 C5 1.382(6) . ?
C5 C6 1.407(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.383(6) . ?
C9 C10 1.394(5) . ?
C9 C18 1.431(6) . ?
C10 C11 1.416(6) . ?
C11 C12 1.361(5) . ?
C12 C13 1.424(5) . ?
C13 C14 1.414(5) . ?
C13 C18 1.427(6) . ?
C14 C15 1.367(6) . ?
C15 C16 1.411(6) . ?
C16 C17 1.359(6) . ?
C17 C18 1.416(6) . ?

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 C8 109.0(3) . . ?
N3 N2 C2 115.2(3) . . ?
N2 N3 C9 115.4(3) . . ?
N1 C1 C2 109.7(3) . . ?
C1 C2 N2 121.2(4) . . ?
C1 C2 C3 107.2(3) . . ?
N2 C2 C3 131.5(4) . . ?
C4 C3 C8 118.4(4) . . ?
C4 C3 C2 135.8(4) . . ?
C8 C3 C2 105.8(3) . . ?
C5 C4 C3 118.5(4) . . ?
C4 C5 C6 121.9(4) . . ?
C7 C6 C5 120.4(4) . . ?
C8 C7 C6 117.6(4) . . ?
C7 C8 N1 128.5(4) . . ?
C7 C8 C3 123.3(3) . . ?
N1 C8 C3 108.2(3) . . ?
C10 C9 N3 124.9(4) . . ?
C10 C9 C18 119.8(4) . . ?
N3 C9 C18 115.3(3) . . ?
O1 C10 C9 121.7(4) . . ?
O1 C10 C11 117.8(3) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C11 C10 120.4(4) . . ?
C11 C12 C13 121.3(4) . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 C18 119.6(4) . . ?
C12 C13 C18 118.9(4) . . ?
C15 C14 C13 119.5(4) . . ?
C14 C15 C16 121.7(4) . . ?
C14 C15 Br1 120.1(3) . . ?
C16 C15 Br1 118.1(3) . . ?
C17 C16 C15 119.3(4) . . ?
C16 C17 C18 121.6(4) . . ?
C17 C18 C13 118.3(4) . . ?
C17 C18 C9 122.7(4) . . ?
C13 C18 C9 119.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.94(6) 2.05(6) 2.931(5) 156(6) 4_554 yes
O1 H1A N2 0.88(8) 1.73(8) 2.536(5) 152(7) . yes

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.087



