# Electronic Supplementary Material (ESI) for ChemComm.
# 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_fokin96
_database_code_depnum_ccdc_archive 'CCDC 2024692'
loop_
_audit_author_name
_audit_author_address
'Anthony Silvestri'
;Unnatural Products Inc
United States of America
;
_audit_update_record             
;
2020-08-21 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2015-07-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Br2 N2 O2'
_chemical_formula_sum            'C24 H22 Br2 N2 O2'
_chemical_formula_weight         530.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.0728(8)
_cell_length_b                   24.305(2)
_cell_length_c                   15.0006(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.929(4)
_cell_angle_gamma                90
_cell_volume                     2187.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7073
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.029
_cell_measurement_theta_min      2.163
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.468
_exptl_absorpt_coefficient_mu    3.730
_exptl_absorpt_correction_T_max  0.0570
_exptl_absorpt_correction_T_min  0.0297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1024 before and 0.0311 after correction.
The Ratio of minimum to maximum transmission is 0.5211.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9162
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_min         2.167
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3230
_reflns_number_total             4022
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0221P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0745
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 1.03248(6) 0.07364(2) 0.97815(2) 0.02046(10) Uani 1 1 d . . . . .
Br2 Br 1.03883(6) 0.00413(2) 0.62002(2) 0.02506(11) Uani 1 1 d . . . . .
O1 O 0.9527(4) -0.04645(9) 0.82824(15) 0.0216(5) Uani 1 1 d . . . . .
O2 O 0.5951(4) 0.16358(9) 0.91445(15) 0.0247(5) Uani 1 1 d . . . . .
N1 N 1.3133(5) -0.01812(11) 0.84583(18) 0.0210(6) Uani 1 1 d . . . . .
N2 N 0.8999(5) 0.21787(11) 0.91610(18) 0.0219(6) Uani 1 1 d . . . . .
C1 C 1.3986(6) -0.07307(14) 0.8703(2) 0.0252(8) Uani 1 1 d . . . . .
H1A H 1.4284 -0.0765 0.9361 0.038 Uiso 1 1 calc GR . . . .
H1B H 1.5370 -0.0791 0.8456 0.038 Uiso 1 1 calc GR . . . .
H1C H 1.2879 -0.1006 0.8455 0.038 Uiso 1 1 calc GR . . . .
C2 C 1.0942(6) -0.01050(13) 0.8246(2) 0.0185(7) Uani 1 1 d . . . . .
C3 C 1.0125(5) 0.04642(13) 0.7928(2) 0.0173(7) Uani 1 1 d . . . . .
C4 C 0.9609(5) 0.05793(13) 0.7017(2) 0.0199(7) Uani 1 1 d . . . . .
C5 C 0.8569(5) 0.10638(13) 0.6677(2) 0.0194(7) Uani 1 1 d . . . . .
C6 C 0.8091(5) 0.14621(13) 0.7299(2) 0.0190(7) Uani 1 1 d . . . . .
C7 C 0.7226(6) 0.20219(13) 0.6993(2) 0.0208(8) Uani 1 1 d . . . . .
C8 C 0.8555(6) 0.23610(14) 0.6546(2) 0.0222(8) Uani 1 1 d . . . . .
H8 H 0.9901 0.2221 0.6386 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7935(6) 0.28982(14) 0.6334(2) 0.0277(9) Uani 1 1 d . . . . .
H9 H 0.8834 0.3123 0.6017 0.033 Uiso 1 1 calc R . . . .
C10 C 0.6002(6) 0.31085(15) 0.6584(2) 0.0283(9) Uani 1 1 d . . . . .
H10 H 0.5594 0.3481 0.6459 0.034 Uiso 1 1 calc R . . . .
C11 C 0.9596(5) 0.08606(13) 0.8519(2) 0.0175(7) Uani 1 1 d . . . . .
C12 C 0.8560(5) 0.13516(13) 0.8229(2) 0.0181(7) Uani 1 1 d . . . . .
C13 C 0.4679(6) 0.27745(14) 0.7015(2) 0.0277(8) Uani 1 1 d . . . . .
H13 H 0.3346 0.2918 0.7182 0.033 Uiso 1 1 calc R . . . .
C14 C 0.5255(6) 0.22311(14) 0.7210(2) 0.0234(8) Uani 1 1 d . . . . .
H14 H 0.4299 0.2002 0.7492 0.028 Uiso 1 1 calc R . . . .
C15 C 0.7784(6) 0.11251(13) 0.5683(2) 0.0216(8) Uani 1 1 d . . . . .
C16 C 0.9169(6) 0.13098(14) 0.5093(2) 0.0239(8) Uani 1 1 d . . . . .
H16 H 1.0647 0.1423 0.5319 0.029 Uiso 1 1 calc R . . . .
C17 C 0.8398(6) 0.13291(14) 0.4170(2) 0.0284(9) Uani 1 1 d . . . . .
H17 H 0.9342 0.1460 0.3768 0.034 Uiso 1 1 calc R . . . .
C18 C 0.6262(6) 0.11583(15) 0.3841(2) 0.0306(9) Uani 1 1 d . . . . .
H18 H 0.5740 0.1171 0.3211 0.037 Uiso 1 1 calc R . . . .
C19 C 0.4888(7) 0.09703(15) 0.4418(2) 0.0330(9) Uani 1 1 d . . . . .
H19 H 0.3417 0.0853 0.4187 0.040 Uiso 1 1 calc R . . . .
C20 C 0.5653(6) 0.09507(15) 0.5344(2) 0.0276(8) Uani 1 1 d . . . . .
H20 H 0.4704 0.0817 0.5743 0.033 Uiso 1 1 calc R . . . .
C21 C 0.7745(5) 0.17390(13) 0.8897(2) 0.0191(7) Uani 1 1 d . . . . .
C22 C 1.1149(6) 0.22860(15) 0.8886(2) 0.0283(9) Uani 1 1 d . . . . .
H22A H 1.1778 0.1941 0.8701 0.042 Uiso 1 1 calc GR . . . .
H22B H 1.2161 0.2445 0.9393 0.042 Uiso 1 1 calc GR . . . .
H22C H 1.0960 0.2545 0.8379 0.042 Uiso 1 1 calc GR . . . .
C23 C 0.8093(6) 0.26040(14) 0.9682(2) 0.0295(9) Uani 1 1 d . . . . .
H23A H 0.7631 0.2920 0.9291 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.9235 0.2720 1.0181 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.6802 0.2458 0.9924 0.044 Uiso 1 1 calc GR . . . .
C24 C 1.4779(6) 0.02531(15) 0.8439(3) 0.0315(9) Uani 1 1 d . . . . .
H24A H 1.5572 0.0195 0.7926 0.047 Uiso 1 1 calc GR . . . .
H24B H 1.5845 0.0245 0.9001 0.047 Uiso 1 1 calc GR . . . .
H24C H 1.4026 0.0611 0.8378 0.047 Uiso 1 1 calc GR . . . .


_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 C11 1.901(3) . ?
Br2 C4 1.901(3) . ?
O1 C2 1.232(4) . ?
O2 C21 1.230(4) . ?
N1 C1 1.459(4) . ?
N1 C2 1.332(4) . ?
N1 C24 1.457(4) . ?
N2 C21 1.336(4) . ?
N2 C22 1.453(4) . ?
N2 C23 1.454(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.521(4) . ?
C3 C4 1.382(4) . ?
C3 C11 1.381(4) . ?
C4 C5 1.395(5) . ?
C5 C6 1.405(5) . ?
C5 C15 1.501(4) . ?
C6 C7 1.504(4) . ?
C6 C12 1.405(4) . ?
C7 C8 1.396(5) . ?
C7 C14 1.385(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(5) . ?
C10 H10 0.9500 . ?
C10 C13 1.372(5) . ?
C11 C12 1.387(4) . ?
C12 C21 1.513(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(5) . ?
C15 C20 1.382(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.370(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.396(5) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C2 N1 C1 119.3(3) . . ?
C2 N1 C24 123.9(3) . . ?
C24 N1 C1 116.8(3) . . ?
C21 N2 C22 123.8(3) . . ?
C21 N2 C23 118.8(3) . . ?
C22 N2 C23 117.2(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 124.6(3) . . ?
O1 C2 C3 117.6(3) . . ?
N1 C2 C3 117.8(3) . . ?
C4 C3 C2 120.5(3) . . ?
C11 C3 C2 122.0(3) . . ?
C11 C3 C4 117.0(3) . . ?
C3 C4 Br2 117.2(2) . . ?
C3 C4 C5 123.5(3) . . ?
C5 C4 Br2 119.3(2) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 C15 120.2(3) . . ?
C6 C5 C15 121.7(3) . . ?
C5 C6 C7 121.3(3) . . ?
C12 C6 C5 119.8(3) . . ?
C12 C6 C7 118.9(3) . . ?
C8 C7 C6 118.7(3) . . ?
C14 C7 C6 122.3(3) . . ?
C14 C7 C8 118.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.3 . . ?
C13 C10 C9 119.5(3) . . ?
C13 C10 H10 120.3 . . ?
C3 C11 Br1 119.2(2) . . ?
C3 C11 C12 122.6(3) . . ?
C12 C11 Br1 118.2(2) . . ?
C6 C12 C21 120.1(3) . . ?
C11 C12 C6 119.2(3) . . ?
C11 C12 C21 120.4(3) . . ?
C10 C13 H13 119.5 . . ?
C10 C13 C14 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C7 C14 C13 120.0(3) . . ?
C7 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C5 122.4(3) . . ?
C20 C15 C5 118.0(3) . . ?
C20 C15 C16 119.4(3) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.2(3) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
O2 C21 N2 124.4(3) . . ?
O2 C21 C12 118.0(3) . . ?
N2 C21 C12 117.6(3) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C11 C12 C6 177.3(2) . . . . ?
Br1 C11 C12 C21 -8.4(4) . . . . ?
Br2 C4 C5 C6 -177.6(2) . . . . ?
Br2 C4 C5 C15 8.6(4) . . . . ?
O1 C2 C3 C4 -82.4(4) . . . . ?
O1 C2 C3 C11 89.1(4) . . . . ?
N1 C2 C3 C4 97.0(4) . . . . ?
N1 C2 C3 C11 -91.5(4) . . . . ?
C1 N1 C2 O1 3.8(5) . . . . ?
C1 N1 C2 C3 -175.5(3) . . . . ?
C2 C3 C4 Br2 -9.3(4) . . . . ?
C2 C3 C4 C5 170.9(3) . . . . ?
C2 C3 C11 Br1 9.7(4) . . . . ?
C2 C3 C11 C12 -170.7(3) . . . . ?
C3 C4 C5 C6 2.2(5) . . . . ?
C3 C4 C5 C15 -171.6(3) . . . . ?
C3 C11 C12 C6 -2.3(5) . . . . ?
C3 C11 C12 C21 172.0(3) . . . . ?
C4 C3 C11 Br1 -178.5(2) . . . . ?
C4 C3 C11 C12 1.1(5) . . . . ?
C4 C5 C6 C7 172.6(3) . . . . ?
C4 C5 C6 C12 -3.3(5) . . . . ?
C4 C5 C15 C16 -86.2(4) . . . . ?
C4 C5 C15 C20 88.8(4) . . . . ?
C5 C6 C7 C8 -61.7(4) . . . . ?
C5 C6 C7 C14 124.2(4) . . . . ?
C5 C6 C12 C11 3.4(5) . . . . ?
C5 C6 C12 C21 -170.9(3) . . . . ?
C5 C15 C16 C17 176.3(3) . . . . ?
C5 C15 C20 C19 -176.4(3) . . . . ?
C6 C5 C15 C16 100.2(4) . . . . ?
C6 C5 C15 C20 -84.7(4) . . . . ?
C6 C7 C8 C9 -173.4(3) . . . . ?
C6 C7 C14 C13 171.5(3) . . . . ?
C6 C12 C21 O2 93.8(4) . . . . ?
C6 C12 C21 N2 -84.5(4) . . . . ?
C7 C6 C12 C11 -172.6(3) . . . . ?
C7 C6 C12 C21 13.1(5) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C8 C7 C14 C13 -2.5(5) . . . . ?
C8 C9 C10 C13 -2.2(5) . . . . ?
C9 C10 C13 C14 0.5(6) . . . . ?
C10 C13 C14 C7 1.9(5) . . . . ?
C11 C3 C4 Br2 178.7(2) . . . . ?
C11 C3 C4 C5 -1.0(5) . . . . ?
C11 C12 C21 O2 -80.4(4) . . . . ?
C11 C12 C21 N2 101.3(4) . . . . ?
C12 C6 C7 C8 114.2(4) . . . . ?
C12 C6 C7 C14 -59.9(5) . . . . ?
C14 C7 C8 C9 0.9(5) . . . . ?
C15 C5 C6 C7 -13.7(5) . . . . ?
C15 C5 C6 C12 170.4(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C15 C20 C19 -1.2(5) . . . . ?
C16 C17 C18 C19 0.1(6) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C15 0.6(6) . . . . ?
C20 C15 C16 C17 1.3(5) . . . . ?
C22 N2 C21 O2 177.9(3) . . . . ?
C22 N2 C21 C12 -3.9(5) . . . . ?
C23 N2 C21 O2 -8.2(5) . . . . ?
C23 N2 C21 C12 169.9(3) . . . . ?
C24 N1 C2 O1 -178.0(3) . . . . ?
C24 N1 C2 C3 2.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fokin97
_database_code_depnum_ccdc_archive 'CCDC 2024693'
loop_
_audit_author_name
_audit_author_address
'Anthony Silvestri'
;Unnatural Products Inc
United States of America
;
_audit_update_record             
;
2020-08-21 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H11 Br2 N O4'
_chemical_formula_sum            'C12 H11 Br2 N O4'
_chemical_formula_weight         393.04
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5662(6)
_cell_length_b                   8.5847(6)
_cell_length_c                   9.5341(6)
_cell_angle_alpha                96.065(2)
_cell_angle_beta                 102.093(2)
_cell_angle_gamma                95.978(2)
_cell_volume                     675.95(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5083
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.687
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.005
_exptl_absorpt_correction_T_max  0.1011
_exptl_absorpt_correction_T_min  0.0535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1023 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.5292.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11041
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.281
_diffrn_reflns_theta_min         2.406
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3026
_reflns_number_total             3881
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+0.2002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 1.07284(3) 0.46503(3) 0.17592(3) 0.02173(8) Uani 1 1 d . . . . .
Br2 Br 0.57209(3) 0.11872(3) 0.36307(3) 0.01591(7) Uani 1 1 d . . . . .
O1 O 1.3937(2) 0.3699(2) 0.5900(2) 0.0197(4) Uani 1 1 d . . . . .
H1 H 1.382(4) 0.437(4) 0.647(3) 0.029 Uiso 1 1 d R . . . .
O2 O 0.7641(2) 0.0234(2) 0.66109(19) 0.0196(4) Uani 1 1 d . . . . .
O3 O 1.0269(2) 0.1123(2) 0.73270(18) 0.0172(4) Uani 1 1 d . . . . .
O4 O 0.6482(2) 0.4409(2) 0.17627(19) 0.0210(4) Uani 1 1 d . . . . .
N1 N 0.6997(3) 0.2310(2) 0.0368(2) 0.0171(4) Uani 1 1 d . . . . .
C1 C 1.1492(3) 0.2056(3) 0.6820(3) 0.0155(5) Uani 1 1 d . . . . .
H1A H 1.2372 0.1435 0.6685 0.019 Uiso 1 1 calc R . . . .
H1B H 1.1950 0.3016 0.7515 0.019 Uiso 1 1 calc R . . . .
C2 C 1.0627(3) 0.2488(3) 0.5398(3) 0.0132(5) Uani 1 1 d . . . . .
C3 C 0.9023(3) 0.1856(3) 0.5165(3) 0.0125(5) Uani 1 1 d . . . . .
C4 C 0.7902(3) 0.2053(3) 0.3933(3) 0.0132(5) Uani 1 1 d . . . . .
C5 C 0.8417(3) 0.2899(3) 0.2914(3) 0.0138(5) Uani 1 1 d . . . . .
C6 C 0.7215(3) 0.3254(3) 0.1616(3) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.5841(3) 0.2635(3) -0.0885(3) 0.0245(6) Uani 1 1 d . . . . .
H7A H 0.4839 0.1918 -0.1018 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.6286 0.2477 -0.1749 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.5621 0.3730 -0.0733 0.037 Uiso 1 1 calc GR . . . .
C8 C 1.2956(3) 0.4002(3) 0.4593(3) 0.0164(5) Uani 1 1 d . . . . .
H8A H 1.3364 0.3532 0.3770 0.020 Uiso 1 1 calc R . . . .
H8B H 1.3038 0.5158 0.4572 0.020 Uiso 1 1 calc R . . . .
C9 C 1.1199(3) 0.3344(3) 0.4405(3) 0.0143(5) Uani 1 1 d . . . . .
C10 C 1.0045(3) 0.3519(3) 0.3182(3) 0.0143(5) Uani 1 1 d . . . . .
C11 C 0.8810(3) 0.0973(3) 0.6386(3) 0.0159(5) Uani 1 1 d . . . . .
C12 C 0.7820(4) 0.0921(3) 0.0179(3) 0.0289(7) Uani 1 1 d . . . . .
H12A H 0.8497 0.0777 0.1110 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.8495 0.1069 -0.0521 0.043 Uiso 1 1 calc GR . . . .
H12C H 0.7021 -0.0015 -0.0177 0.043 Uiso 1 1 calc GR . . . .


_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 C10 1.903(2) . ?
Br2 C4 1.889(2) . ?
O1 H1 0.78(3) . ?
O1 C8 1.415(3) . ?
O2 C11 1.199(3) . ?
O3 C1 1.446(3) . ?
O3 C11 1.362(3) . ?
O4 C6 1.239(3) . ?
N1 C6 1.334(3) . ?
N1 C7 1.456(3) . ?
N1 C12 1.461(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.505(3) . ?
C2 C3 1.387(3) . ?
C2 C9 1.394(3) . ?
C3 C4 1.391(3) . ?
C3 C11 1.487(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.515(3) . ?
C5 C10 1.400(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.518(3) . ?
C9 C10 1.394(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C8 O1 H1 103(2) . . ?
C11 O3 C1 111.45(18) . . ?
C6 N1 C7 119.0(2) . . ?
C6 N1 C12 124.0(2) . . ?
C7 N1 C12 117.0(2) . . ?
O3 C1 H1A 110.8 . . ?
O3 C1 H1B 110.8 . . ?
O3 C1 C2 104.74(19) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C3 C2 C1 107.7(2) . . ?
C3 C2 C9 121.7(2) . . ?
C9 C2 C1 130.6(2) . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 C11 108.7(2) . . ?
C4 C3 C11 129.7(2) . . ?
C3 C4 Br2 121.18(18) . . ?
C5 C4 Br2 120.15(18) . . ?
C5 C4 C3 118.7(2) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 C10 118.2(2) . . ?
C10 C5 C6 121.2(2) . . ?
O4 C6 N1 123.1(2) . . ?
O4 C6 C5 118.5(2) . . ?
N1 C6 C5 118.5(2) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 H8A 109.0 . . ?
O1 C8 H8B 109.0 . . ?
O1 C8 C9 113.0(2) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C2 C9 C8 123.3(2) . . ?
C10 C9 C2 115.2(2) . . ?
C10 C9 C8 121.5(2) . . ?
C5 C10 Br1 117.44(18) . . ?
C9 C10 Br1 117.94(18) . . ?
C9 C10 C5 124.6(2) . . ?
O2 C11 O3 121.6(2) . . ?
O2 C11 C3 131.0(2) . . ?
O3 C11 C3 107.4(2) . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br2 C4 C5 C6 5.2(3) . . . . ?
Br2 C4 C5 C10 -179.98(17) . . . . ?
O1 C8 C9 C2 -1.9(3) . . . . ?
O1 C8 C9 C10 -179.8(2) . . . . ?
O3 C1 C2 C3 1.2(3) . . . . ?
O3 C1 C2 C9 -178.3(2) . . . . ?
C1 O3 C11 O2 179.7(2) . . . . ?
C1 O3 C11 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C11 -1.5(3) . . . . ?
C1 C2 C9 C8 1.9(4) . . . . ?
C1 C2 C9 C10 179.9(2) . . . . ?
C2 C3 C4 Br2 -179.90(18) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C11 O2 -178.9(3) . . . . ?
C2 C3 C11 O3 1.2(3) . . . . ?
C2 C9 C10 Br1 -179.26(17) . . . . ?
C2 C9 C10 C5 -0.3(4) . . . . ?
C3 C2 C9 C8 -177.6(2) . . . . ?
C3 C2 C9 C10 0.4(3) . . . . ?
C3 C4 C5 C6 -175.1(2) . . . . ?
C3 C4 C5 C10 -0.3(3) . . . . ?
C4 C3 C11 O2 -0.4(5) . . . . ?
C4 C3 C11 O3 179.6(2) . . . . ?
C4 C5 C6 O4 83.1(3) . . . . ?
C4 C5 C6 N1 -96.9(3) . . . . ?
C4 C5 C10 Br1 179.21(17) . . . . ?
C4 C5 C10 C9 0.3(4) . . . . ?
C6 C5 C10 Br1 -6.0(3) . . . . ?
C6 C5 C10 C9 175.1(2) . . . . ?
C7 N1 C6 O4 -0.3(4) . . . . ?
C7 N1 C6 C5 179.8(2) . . . . ?
C8 C9 C10 Br1 -1.2(3) . . . . ?
C8 C9 C10 C5 177.8(2) . . . . ?
C9 C2 C3 C4 -0.5(4) . . . . ?
C9 C2 C3 C11 178.1(2) . . . . ?
C10 C5 C6 O4 -91.5(3) . . . . ?
C10 C5 C6 N1 88.4(3) . . . . ?
C11 O3 C1 C2 -0.5(3) . . . . ?
C11 C3 C4 Br2 1.8(4) . . . . ?
C11 C3 C4 C5 -177.9(2) . . . . ?
C12 N1 C6 O4 -178.5(3) . . . . ?
C12 N1 C6 C5 1.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
