# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_D18101
_database_code_depnum_ccdc_archive 'CCDC 2093273'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT987_D18101              
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: The s.u. of Flack x and Parsons parameter are probably 
          underestimated. Synthetic protocoll and also Bayesian statistics
          indicate enantiopure sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            33
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Br N O4'
_chemical_formula_weight         460.36

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                   11.0574(6)
_cell_length_b                   7.5672(4)
_cell_length_c                   13.7732(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.450(3)
_cell_angle_gamma                90
_cell_volume                     1072.63(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9168
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      37.81

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    1.945
_shelx_estimated_absorpt_T_min   0.501
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            140952
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         35.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9856
_reflns_number_gt                9193
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.985

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.0305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 4020 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0206(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9856
_refine_ls_number_parameters     268
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0535
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.33511(2) 0.84054(2) 0.08630(2) 0.01483(3) Uani 1 1 d . . . . .
O1 O 0.47296(11) 0.6081(2) 0.41223(9) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.40749(11) 0.3396(3) 0.34858(8) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.08129(10) 0.62867(15) 0.16242(8) 0.01609(19) Uani 1 1 d . . . . .
O4 O 0.14076(10) 0.15722(14) 0.01699(9) 0.01521(19) Uani 1 1 d D . . . .
H4 H 0.0834(19) 0.131(3) -0.0385(15) 0.023 Uiso 1 1 d D U . . .
N1 N 0.27680(11) 0.58947(17) 0.28727(9) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.09644(15) 0.5289(3) 0.42756(13) 0.0224(3) Uani 1 1 d . . . . .
H1 H 0.035243 0.529892 0.357958 0.027 Uiso 1 1 calc R U . . .
C2 C 0.0913(2) 0.3950(3) 0.49476(16) 0.0313(4) Uani 1 1 d . . . . .
H2 H 0.026725 0.305611 0.471337 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1808(2) 0.3923(3) 0.59638(16) 0.0334(4) Uani 1 1 d . . . . .
H3 H 0.177406 0.301475 0.642924 0.040 Uiso 1 1 calc R U . . .
C4 C 0.27487(19) 0.5219(3) 0.62964(13) 0.0285(4) Uani 1 1 d . . . . .
H4A H 0.336752 0.518980 0.698968 0.034 Uiso 1 1 calc R U . . .
C5 C 0.27984(16) 0.6569(2) 0.56243(12) 0.0212(3) Uani 1 1 d . . . . .
H5 H 0.344695 0.745796 0.586172 0.025 Uiso 1 1 calc R U . . .
C6 C 0.18978(14) 0.6618(2) 0.46034(11) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.19038(15) 0.80603(19) 0.38500(11) 0.0194(3) Uani 1 1 d . . . . .
H7A H 0.216479 0.918113 0.424199 0.023 Uiso 1 1 calc R U . . .
H7AB H 0.100747 0.821555 0.334026 0.023 Uiso 1 1 calc R U . . .
C8 C 0.28122(15) 0.7721(2) 0.32479(11) 0.0172(3) Uani 1 1 d . . . . .
H8 H 0.258472 0.855040 0.264189 0.021 Uiso 1 1 calc R U . . .
C9 C 0.42664(16) 0.7879(3) 0.39007(13) 0.0262(3) Uani 1 1 d . . . . .
H9A H 0.472504 0.850474 0.350525 0.031 Uiso 1 1 calc R U . . .
H9AB H 0.440521 0.853280 0.455531 0.031 Uiso 1 1 calc R U . . .
C10 C 0.38779(14) 0.4950(3) 0.34814(11) 0.0199(3) Uani 1 1 d . . . . .
C11 C 0.17360(12) 0.52882(18) 0.20154(10) 0.0114(2) Uani 1 1 d . . . . .
C12 C 0.17701(10) 0.3438(3) 0.16203(9) 0.01214(17) Uani 1 1 d . . . . .
H12 H 0.268836 0.300659 0.190081 0.015 Uiso 1 1 calc R U . . .
C13 C 0.09490(16) 0.2256(2) 0.20526(13) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.004461 0.266119 0.177997 0.032 Uiso 1 1 calc R U . . .
H13B H 0.129060 0.232511 0.281598 0.032 Uiso 1 1 calc R U . . .
H13C H 0.098970 0.103050 0.183680 0.032 Uiso 1 1 calc R U . . .
C14 C 0.12701(10) 0.3372(3) 0.04221(9) 0.01139(17) Uani 1 1 d . . . . .
H14 H 0.032627 0.368600 0.014142 0.014 Uiso 1 1 calc R U . . .
C15 C 0.20038(12) 0.46481(17) -0.00520(10) 0.0110(2) Uani 1 1 d . . . . .
H15 H 0.167597 0.586918 -0.001769 0.013 Uiso 1 1 calc R U . . .
C16 C 0.16959(14) 0.4211(2) -0.12050(11) 0.0159(2) Uani 1 1 d . . . . .
H16A H 0.075415 0.408868 -0.156237 0.024 Uiso 1 1 calc R U . . .
H16B H 0.212264 0.310065 -0.125940 0.024 Uiso 1 1 calc R U . . .
H16C H 0.201416 0.516512 -0.152992 0.024 Uiso 1 1 calc R U . . .
C17 C 0.34587(12) 0.46589(17) 0.05430(10) 0.0108(2) Uani 1 1 d . . . . .
C18 C 0.41688(13) 0.61487(18) 0.10166(10) 0.0117(2) Uani 1 1 d . . . . .
C19 C 0.55013(13) 0.60911(19) 0.15924(11) 0.0143(2) Uani 1 1 d . . . . .
H19 H 0.594785 0.713657 0.190925 0.017 Uiso 1 1 calc R U . . .
C20 C 0.61769(13) 0.4510(2) 0.17037(12) 0.0155(2) Uani 1 1 d . . . . .
C21 C 0.54907(13) 0.30070(18) 0.12216(11) 0.0145(3) Uani 1 1 d . . . . .
H21 H 0.593601 0.191461 0.128282 0.017 Uiso 1 1 calc R U . . .
C22 C 0.41640(13) 0.30860(16) 0.06528(10) 0.0125(2) Uani 1 1 d . . . . .
H22 H 0.372179 0.204226 0.032873 0.015 Uiso 1 1 calc R U . . .
C23 C 0.76231(15) 0.4431(2) 0.22997(15) 0.0258(3) Uani 1 1 d . . . . .
H23A H 0.807575 0.502603 0.189884 0.039 Uiso 1 1 calc R U . . .
H23B H 0.790145 0.319343 0.241276 0.039 Uiso 1 1 calc R U . . .
H23C H 0.783196 0.502090 0.297481 0.039 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 C18 1.9075(14) . ?
O1 C10 1.338(2) . ?
O1 C9 1.446(3) . ?
O2 C10 1.195(3) . ?
O3 C11 1.2251(16) . ?
O4 C14 1.427(2) . ?
O4 H4 0.818(18) . ?
N1 C11 1.3862(17) . ?
N1 C10 1.4026(19) . ?
N1 C8 1.470(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.508(2) . ?
C7 C8 1.540(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.533(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C11 C12 1.507(2) . ?
C12 C14 1.5377(15) . ?
C12 C13 1.541(2) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.551(2) . ?
C14 H14 1.0000 . ?
C15 C17 1.5150(18) . ?
C15 C16 1.5335(19) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3923(18) . ?
C17 C22 1.4005(17) . ?
C18 C19 1.3955(19) . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(2) . ?
C20 C23 1.508(2) . ?
C21 C22 1.3889(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C10 O1 C9 110.67(12) . . ?
C14 O4 H4 109.9(18) . . ?
C11 N1 C10 127.45(13) . . ?
C11 N1 C8 121.46(12) . . ?
C10 N1 C8 111.08(12) . . ?
C2 C1 C6 121.16(16) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 119.68(18) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 119.84(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.56(16) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.15(16) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.60(15) . . ?
C1 C6 C7 119.27(13) . . ?
C5 C6 C7 122.12(14) . . ?
C6 C7 C8 114.70(13) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7AB 108.6 . . ?
C8 C7 H7AB 108.6 . . ?
H7A C7 H7AB 107.6 . . ?
N1 C8 C9 99.91(13) . . ?
N1 C8 C7 113.67(12) . . ?
C9 C8 C7 114.96(13) . . ?
N1 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
O1 C9 C8 105.38(13) . . ?
O1 C9 H9A 110.7 . . ?
C8 C9 H9A 110.7 . . ?
O1 C9 H9AB 110.7 . . ?
C8 C9 H9AB 110.7 . . ?
H9A C9 H9AB 108.8 . . ?
O2 C10 O1 122.88(14) . . ?
O2 C10 N1 128.49(15) . . ?
O1 C10 N1 108.60(15) . . ?
O3 C11 N1 117.67(13) . . ?
O3 C11 C12 122.74(12) . . ?
N1 C11 C12 119.57(11) . . ?
C11 C12 C14 111.79(14) . . ?
C11 C12 C13 107.67(11) . . ?
C14 C12 C13 111.37(13) . . ?
C11 C12 H12 108.6 . . ?
C14 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C12 105.30(14) . . ?
O4 C14 C15 111.91(10) . . ?
C12 C14 C15 113.17(12) . . ?
O4 C14 H14 108.8 . . ?
C12 C14 H14 108.8 . . ?
C15 C14 H14 108.8 . . ?
C17 C15 C16 110.55(11) . . ?
C17 C15 C14 113.03(10) . . ?
C16 C15 C14 110.46(11) . . ?
C17 C15 H15 107.5 . . ?
C16 C15 H15 107.5 . . ?
C14 C15 H15 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 116.18(12) . . ?
C18 C17 C15 124.27(12) . . ?
C22 C17 C15 119.54(11) . . ?
C17 C18 C19 122.57(13) . . ?
C17 C18 Br1 120.65(10) . . ?
C19 C18 Br1 116.75(10) . . ?
C20 C19 C18 120.20(13) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 118.25(12) . . ?
C19 C20 C23 120.98(14) . . ?
C21 C20 C23 120.74(14) . . ?
C22 C21 C20 120.83(12) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C17 121.95(12) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O4 H4 O3 0.818(18) 1.989(18) 2.7827(14) 163(2) 2_545 yes

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_D18127
_database_code_depnum_ccdc_archive 'CCDC 2093275'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            SI-6
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H33 Br N2 O5'
_chemical_formula_weight         521.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.7555(15)
_cell_length_b                   9.6510(14)
_cell_length_c                   12.0461(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.244(5)
_cell_angle_gamma                90
_cell_volume                     1249.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.55

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    1.682
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_T_max  0.7359
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39593
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5524
_reflns_number_gt                4981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0208P)²+0.0367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 2110 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
 Accuracy of Parsons parameter determination was overestimated,
 classical Flack x determination was used.
;
_refine_ls_abs_structure_Flack   0.012(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5524
_refine_ls_number_parameters     309
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.54546(3) 0.47202(3) 0.96922(2) 0.01950(9) Uani 1 1 d . . . . .
O1 O 0.2724(2) 0.5436(2) 0.63378(18) 0.0143(5) Uani 1 1 d D . . . .
H1 H 0.269(3) 0.465(3) 0.611(3) 0.021 Uiso 1 1 d D U . . .
O2 O 0.49767(19) 0.4505(2) 0.50816(17) 0.0133(5) Uani 1 1 d . . . . .
O3 O 0.73992(18) 0.5761(2) 0.34907(18) 0.0137(5) Uani 1 1 d . . . . .
O4 O 0.7937(2) 0.7714(2) 0.44659(19) 0.0184(5) Uani 1 1 d . . . . .
O5 O 0.8787(2) 0.4219(2) 0.4666(2) 0.0169(5) Uani 1 1 d . . . . .
N1 N 0.5001(2) 0.6621(3) 0.4266(2) 0.0094(5) Uani 1 1 d D . . . .
H1A H 0.500(3) 0.749(2) 0.434(3) 0.011 Uiso 1 1 d D U . . .
N2 N 0.8682(3) 0.5609(3) 0.4977(3) 0.0177(7) Uani 1 1 d . . . . .
C1 C 0.3679(3) 0.4528(4) 0.9550(2) 0.0143(7) Uani 1 1 d . . . . .
C2 C 0.3163(3) 0.3540(3) 1.0226(3) 0.0184(7) Uani 1 1 d . . . . .
H2 H 0.368576 0.299429 1.070554 0.022 Uiso 1 1 calc R U . . .
C3 C 0.1878(3) 0.3343(3) 1.0205(3) 0.0206(7) Uani 1 1 d . . . . .
C4 C 0.1302(4) 0.2288(4) 1.0949(3) 0.0305(9) Uani 1 1 d . . . . .
H4A H 0.146273 0.255072 1.172698 0.046 Uiso 1 1 calc R U . . .
H4B H 0.166644 0.137564 1.081455 0.046 Uiso 1 1 calc R U . . .
H4C H 0.040242 0.225188 1.078840 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1157(3) 0.4163(3) 0.9481(3) 0.0202(7) Uani 1 1 d . . . . .
H5 H 0.027814 0.405608 0.945421 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1692(3) 0.5130(3) 0.8800(3) 0.0167(7) Uani 1 1 d . . . . .
H6 H 0.117096 0.565694 0.830481 0.020 Uiso 1 1 calc R U . . .
C7 C 0.2978(3) 0.5357(3) 0.8819(2) 0.0124(6) Uani 1 1 d . . . . .
C8 C 0.3552(3) 0.6398(3) 0.8050(3) 0.0126(6) Uani 1 1 d . . . . .
H8 H 0.435494 0.671089 0.841394 0.015 Uiso 1 1 calc R U . . .
C9 C 0.2745(3) 0.7688(3) 0.7849(3) 0.0188(7) Uani 1 1 d . . . . .
H9A H 0.321322 0.837852 0.743966 0.028 Uiso 1 1 calc R U . . .
H9B H 0.251594 0.807689 0.856400 0.028 Uiso 1 1 calc R U . . .
H9C H 0.198989 0.743336 0.741475 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3868(3) 0.5668(3) 0.6950(2) 0.0104(6) Uani 1 1 d . . . . .
H10 H 0.426031 0.475194 0.713044 0.012 Uiso 1 1 calc R U . . .
C11 C 0.4760(3) 0.6510(3) 0.6250(3) 0.0126(6) Uani 1 1 d . . . . .
H11 H 0.439625 0.745086 0.610950 0.015 Uiso 1 1 calc R U . . .
C12 C 0.6055(3) 0.6671(4) 0.6813(3) 0.0221(8) Uani 1 1 d . . . . .
H12A H 0.639262 0.575391 0.700162 0.033 Uiso 1 1 calc R U . . .
H12B H 0.599312 0.722223 0.749167 0.033 Uiso 1 1 calc R U . . .
H12C H 0.660748 0.713938 0.630480 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4911(3) 0.5784(3) 0.5148(2) 0.0093(6) Uani 1 1 d . . . . .
C14 C 0.5200(3) 0.6137(3) 0.3144(2) 0.0097(6) Uani 1 1 d . . . . .
H14 H 0.511475 0.510510 0.313398 0.012 Uiso 1 1 calc R U . . .
C15 C 0.6506(3) 0.6505(3) 0.2798(3) 0.0138(7) Uani 1 1 d . . . . .
H15A H 0.660456 0.625347 0.200977 0.017 Uiso 1 1 calc R U . . .
H15B H 0.664462 0.751467 0.287861 0.017 Uiso 1 1 calc R U . . .
C16 C 0.8005(3) 0.6470(3) 0.4315(3) 0.0143(7) Uani 1 1 d . . . . .
C17 C 0.9594(3) 0.6067(4) 0.5825(3) 0.0247(8) Uani 1 1 d . . . . .
H17A H 1.037681 0.556533 0.573852 0.037 Uiso 1 1 calc R U . . .
H17B H 0.928019 0.588106 0.656258 0.037 Uiso 1 1 calc R U . . .
H17C H 0.973999 0.706387 0.574281 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8030(3) 0.3387(4) 0.5355(3) 0.0230(8) Uani 1 1 d . . . . .
H18A H 0.719334 0.378643 0.537038 0.035 Uiso 1 1 calc R U . . .
H18B H 0.840085 0.336121 0.611136 0.035 Uiso 1 1 calc R U . . .
H18C H 0.797827 0.244330 0.505641 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4229(3) 0.6746(3) 0.2317(3) 0.0134(6) Uani 1 1 d . . . . .
H19A H 0.424045 0.776692 0.239616 0.016 Uiso 1 1 calc R U . . .
H19B H 0.448487 0.652724 0.155578 0.016 Uiso 1 1 calc R U . . .
C20 C 0.2902(3) 0.6249(3) 0.2432(3) 0.0128(6) Uani 1 1 d . . . . .
C21 C 0.2563(3) 0.5268(3) 0.3206(3) 0.0138(6) Uani 1 1 d . . . . .
H21 H 0.318460 0.486289 0.368483 0.017 Uiso 1 1 calc R U . . .
C22 C 0.1331(2) 0.4867(4) 0.3292(2) 0.0161(7) Uani 1 1 d . . . . .
H22 H 0.111572 0.421017 0.383959 0.019 Uiso 1 1 calc R U . . .
C23 C 0.0414(3) 0.5418(4) 0.2587(3) 0.0222(8) Uani 1 1 d . . . . .
H23 H -0.042814 0.513853 0.264198 0.027 Uiso 1 1 calc R U . . .
C24 C 0.0740(3) 0.6383(4) 0.1798(3) 0.0238(8) Uani 1 1 d . . . . .
H24 H 0.011937 0.675843 0.130280 0.029 Uiso 1 1 calc R U . . .
C25 C 0.1972(3) 0.6805(4) 0.1728(3) 0.0204(7) Uani 1 1 d . . . . .
H25 H 0.218116 0.748087 0.119278 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
Br1 C1 1.920(3) . ?
O1 C10 1.427(4) . ?
O1 H1 0.81(2) . ?
O2 C13 1.239(4) . ?
O3 C16 1.352(4) . ?
O3 C15 1.439(4) . ?
O4 C16 1.217(4) . ?
O5 N2 1.399(3) . ?
O5 C18 1.432(4) . ?
N1 C13 1.340(4) . ?
N1 C14 1.454(4) . ?
N1 H1A 0.84(2) . ?
N2 C16 1.346(4) . ?
N2 C17 1.457(5) . ?
C1 C2 1.384(5) . ?
C1 C7 1.390(4) . ?
C2 C3 1.394(5) . ?
C2 H2 0.9500 . ?
C3 C5 1.391(5) . ?
C3 C4 1.505(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.514(4) . ?
C8 C9 1.532(4) . ?
C8 C10 1.549(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.534(4) . ?
C10 H10 1.0000 . ?
C11 C13 1.516(4) . ?
C11 C12 1.533(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.523(4) . ?
C14 C19 1.532(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.518(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.387(4) . ?
C20 C25 1.394(5) . ?
C21 C22 1.388(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(5) . ?
C24 H24 0.9500 . ?
C25 H25 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
C10 O1 H1 110(2) . . ?
C16 O3 C15 117.7(2) . . ?
N2 O5 C18 109.2(3) . . ?
C13 N1 C14 124.1(3) . . ?
C13 N1 H1A 121(2) . . ?
C14 N1 H1A 115(2) . . ?
C16 N2 O5 118.7(3) . . ?
C16 N2 C17 124.2(3) . . ?
O5 N2 C17 114.8(3) . . ?
C2 C1 C7 123.3(3) . . ?
C2 C1 Br1 115.8(2) . . ?
C7 C1 Br1 120.9(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C5 C3 C2 117.5(3) . . ?
C5 C3 C4 121.7(3) . . ?
C2 C3 C4 120.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C3 C5 H5 119.3 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C1 C7 C6 115.6(3) . . ?
C1 C7 C8 123.1(3) . . ?
C6 C7 C8 121.3(3) . . ?
C7 C8 C9 113.2(3) . . ?
C7 C8 C10 109.3(2) . . ?
C9 C8 C10 112.1(3) . . ?
C7 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C8 H8 107.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 110.1(2) . . ?
O1 C10 C8 107.4(2) . . ?
C11 C10 C8 113.1(2) . . ?
O1 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C8 C10 H10 108.7 . . ?
C13 C11 C12 107.9(2) . . ?
C13 C11 C10 109.1(2) . . ?
C12 C11 C10 112.8(3) . . ?
C13 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C10 C11 H11 109.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 N1 122.9(3) . . ?
O2 C13 C11 121.7(3) . . ?
N1 C13 C11 115.4(3) . . ?
N1 C14 C15 110.5(2) . . ?
N1 C14 C19 111.1(2) . . ?
C15 C14 C19 110.2(2) . . ?
N1 C14 H14 108.3 . . ?
C15 C14 H14 108.3 . . ?
C19 C14 H14 108.3 . . ?
O3 C15 C14 109.1(2) . . ?
O3 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
O3 C15 H15B 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O4 C16 N2 123.7(3) . . ?
O4 C16 O3 125.4(3) . . ?
N2 C16 O3 110.9(3) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C14 116.0(3) . . ?
C20 C19 H19A 108.3 . . ?
C14 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C14 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C25 118.1(3) . . ?
C21 C20 C19 123.4(3) . . ?
C25 C20 C19 118.5(3) . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?

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 O4 0.81(2) 2.10(3) 2.879(3) 163(3) 2_646 yes
N1 H1A O2 0.84(2) 2.06(2) 2.892(3) 167(3) 2_656 yes

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_D18103
_database_code_depnum_ccdc_archive 'CCDC 2093274'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT987_D18103              
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: Bayesian statistics and synthetic protocoll indicate pure
          enantiomer. s.u. probably underestimated.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            epi-26
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 Br N O3'
_chemical_formula_weight         344.24

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

_cell_length_a                   8.1889(4)
_cell_length_b                   10.6443(5)
_cell_length_c                   18.0654(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9267
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      32.55

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    2.617
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5115
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            110262
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         33.132
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5998
_reflns_number_gt                5596
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     1.000
_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+0.1654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Classical Flack x determined. 
;
_refine_ls_abs_structure_Flack   0.018(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5998
_refine_ls_number_parameters     189
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.004
_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 0.58479(2) 0.24320(2) 0.61867(2) 0.01435(4) Uani 1 1 d . . . . .
O1 O 0.49355(15) 0.50248(13) 0.80040(8) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.85604(16) 0.33274(13) 0.78280(7) 0.0170(3) Uani 1 1 d . . . . .
O3 O 0.96897(19) 0.64468(13) 0.65049(8) 0.0235(3) Uani 1 1 d D . . . .
H3 H 1.011(3) 0.692(2) 0.6785(14) 0.035 Uiso 1 1 d D U . . .
N1 N 0.5993(2) 0.39867(14) 0.80068(8) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.3690(2) 0.4859(2) 0.74558(12) 0.0231(4) Uani 1 1 d . . . . .
H1A H 0.294544 0.558027 0.746619 0.035 Uiso 1 1 calc R U . . .
H1B H 0.307717 0.408886 0.756085 0.035 Uiso 1 1 calc R U . . .
H1C H 0.419409 0.479616 0.696526 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5486(3) 0.29775(19) 0.84943(12) 0.0230(4) Uani 1 1 d . . . . .
H2A H 0.446585 0.261117 0.831083 0.035 Uiso 1 1 calc R U . . .
H2B H 0.531526 0.330981 0.899423 0.035 Uiso 1 1 calc R U . . .
H2C H 0.633586 0.232937 0.850741 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7530(2) 0.41570(16) 0.77539(9) 0.0121(3) Uani 1 1 d . . . . .
C4 C 0.7929(2) 0.54071(16) 0.73942(10) 0.0122(3) Uani 1 1 d . . . . .
H4 H 0.693268 0.573511 0.713916 0.015 Uiso 1 1 calc R U . . .
C5 C 0.8420(2) 0.63222(17) 0.80138(11) 0.0197(4) Uani 1 1 d . . . . .
H5A H 0.865627 0.714866 0.779997 0.030 Uiso 1 1 calc R U . . .
H5B H 0.939503 0.600398 0.826656 0.030 Uiso 1 1 calc R U . . .
H5C H 0.752264 0.639734 0.836981 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9309(2) 0.52657(16) 0.68267(9) 0.0135(3) Uani 1 1 d . . . . .
H6 H 1.030148 0.495959 0.709412 0.016 Uiso 1 1 calc R U . . .
C7 C 0.89443(19) 0.43412(15) 0.61956(9) 0.0130(3) Uani 1 1 d . . . . .
H7 H 0.868606 0.351141 0.642727 0.016 Uiso 1 1 calc R U . . .
C8 C 1.0478(2) 0.4160(2) 0.57202(11) 0.0220(4) Uani 1 1 d . . . . .
H8A H 1.025388 0.354408 0.533006 0.033 Uiso 1 1 calc R U . . .
H8B H 1.137490 0.385681 0.603189 0.033 Uiso 1 1 calc R U . . .
H8C H 1.078586 0.496344 0.549496 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7490(2) 0.47051(15) 0.57187(9) 0.0120(3) Uani 1 1 d . . . . .
C10 C 0.7509(2) 0.58013(16) 0.52875(10) 0.0160(3) Uani 1 1 d . . . . .
H10 H 0.843916 0.633376 0.530897 0.019 Uiso 1 1 calc R U . . .
C11 C 0.6220(2) 0.61342(17) 0.48316(10) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.627785 0.689352 0.455647 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4838(2) 0.53740(17) 0.47692(10) 0.0138(3) Uani 1 1 d . . . . .
C13 C 0.4794(2) 0.42760(16) 0.51860(10) 0.0129(3) Uani 1 1 d . . . . .
H13 H 0.387428 0.373453 0.515330 0.016 Uiso 1 1 calc R U . . .
C14 C 0.6088(2) 0.39653(15) 0.56507(9) 0.0115(3) Uani 1 1 d . . . . .
C15 C 0.3436(2) 0.57263(18) 0.42730(11) 0.0196(4) Uani 1 1 d . . . . .
H15A H 0.385923 0.611218 0.381929 0.029 Uiso 1 1 calc R U . . .
H15B H 0.272542 0.632504 0.452983 0.029 Uiso 1 1 calc R U . . .
H15C H 0.281098 0.497125 0.414647 0.029 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 C14 1.9078(16) . ?
O1 N1 1.4038(19) . ?
O1 C1 1.433(2) . ?
O2 C3 1.229(2) . ?
O3 C6 1.420(2) . ?
O3 H3 0.79(2) . ?
N1 C3 1.351(2) . ?
N1 C2 1.450(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.517(2) . ?
C4 C6 1.533(2) . ?
C4 C5 1.537(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.535(2) . ?
C6 H6 1.0000 . ?
C7 C9 1.520(2) . ?
C7 C8 1.534(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.398(2) . ?
C9 C10 1.403(2) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C15 1.504(2) . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
N1 O1 C1 110.18(13) . . ?
C6 O3 H3 113(2) . . ?
C3 N1 O1 117.89(14) . . ?
C3 N1 C2 124.84(16) . . ?
O1 N1 C2 114.15(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 C3 N1 120.44(16) . . ?
O2 C3 C4 121.93(16) . . ?
N1 C3 C4 117.62(15) . . ?
C3 C4 C6 111.07(14) . . ?
C3 C4 C5 107.48(14) . . ?
C6 C4 C5 110.87(14) . . ?
C3 C4 H4 109.1 . . ?
C6 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 C4 110.41(14) . . ?
O3 C6 C7 107.83(13) . . ?
C4 C6 C7 114.58(14) . . ?
O3 C6 H6 107.9 . . ?
C4 C6 H6 107.9 . . ?
C7 C6 H6 107.9 . . ?
C9 C7 C8 110.88(14) . . ?
C9 C7 C6 114.20(14) . . ?
C8 C7 C6 109.70(14) . . ?
C9 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 115.42(16) . . ?
C14 C9 C7 123.36(14) . . ?
C10 C9 C7 121.17(15) . . ?
C11 C10 C9 122.29(17) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 121.18(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 117.68(16) . . ?
C13 C12 C15 120.82(16) . . ?
C11 C12 C15 121.50(16) . . ?
C12 C13 C14 120.43(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 122.99(15) . . ?
C13 C14 Br1 115.54(12) . . ?
C9 C14 Br1 121.46(13) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O3 H3 O2 0.79(2) 1.98(2) 2.7409(18) 161(3) 3_756 yes

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.067

