# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
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data_mw410_a
_database_code_depnum_ccdc_archive 'CCDC 2116284'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.359 H13.077 Br0.641 N O'
_chemical_formula_sum            'C19.36 H13.07 Br0.64 N O'
_chemical_formula_weight         327.01
_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      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                   11.5265(6)
_cell_length_b                   10.1543(5)
_cell_length_c                   12.3229(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.063(2)
_cell_angle_gamma                90
_cell_volume                     1436.69(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9191
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.489
_cell_measurement_theta_min      2.320
_shelx_estimated_absorpt_T_max   0.538
_shelx_estimated_absorpt_T_min   0.523
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0934 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.6171.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             667
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.379
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.563
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3683
_reflns_number_total             4369
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     354
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.002
_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)+(0.0387P)²+0.8056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0815
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C1) = Uanis(C2)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.60342(10) 0.13985(12) 0.78476(9) 0.0224(3) Uani 1 1 d . U . . .
N1 N 0.65893(10) 0.19852(12) 0.61933(9) 0.0115(2) Uani 1 1 d . U . . .
C2 C 0.48398(12) 0.61005(15) 0.78153(11) 0.0139(3) Uani 1 1 d . U . . .
C3 C 0.54453(12) 0.53787(15) 0.86433(11) 0.0150(3) Uani 1 1 d . U . . .
H3 H 0.557021 0.573582 0.935660 0.018 Uiso 1 1 calc R U . . .
C4 C 0.58649(12) 0.41368(15) 0.84221(10) 0.0144(3) Uani 1 1 d . U . . .
H4 H 0.625641 0.363034 0.899026 0.017 Uiso 1 1 calc R U . . .
C5 C 0.57130(11) 0.36272(15) 0.73638(10) 0.0116(3) Uani 1 1 d . U . . .
C6 C 0.50875(12) 0.43527(15) 0.65438(10) 0.0126(3) Uani 1 1 d . U . . .
H6 H 0.496960 0.400215 0.582780 0.015 Uiso 1 1 calc R U . . .
C7 C 0.46374(12) 0.55810(15) 0.67679(11) 0.0134(3) Uani 1 1 d . U . . .
H7 H 0.419634 0.606268 0.621388 0.016 Uiso 1 1 calc R U . . .
C8 C 0.61298(12) 0.22647(15) 0.71808(10) 0.0132(3) Uani 1 1 d . U . . .
C9 C 0.65573(11) 0.07190(14) 0.57095(10) 0.0122(3) Uani 1 1 d . U . . .
C10 C 0.60915(12) -0.04510(15) 0.60630(12) 0.0158(3) Uani 1 1 d . U . . .
H10 H 0.573773 -0.049661 0.672972 0.019 Uiso 1 1 calc R U . . .
C11 C 0.61638(13) -0.15505(16) 0.54029(13) 0.0194(3) Uani 1 1 d . U . . .
H11 H 0.585897 -0.236533 0.562839 0.023 Uiso 1 1 calc R U . . .
C12 C 0.66736(13) -0.14916(16) 0.44142(13) 0.0195(3) Uani 1 1 d . U . . .
H12 H 0.670420 -0.226009 0.397798 0.023 Uiso 1 1 calc R U . . .
C13 C 0.71336(12) -0.03205(15) 0.40680(11) 0.0160(3) Uani 1 1 d . U . . .
H13 H 0.747805 -0.027770 0.339636 0.019 Uiso 1 1 calc R U . . .
C14 C 0.70828(11) 0.07945(14) 0.47217(10) 0.0123(3) Uani 1 1 d . U . . .
C15 C 0.75187(11) 0.21246(14) 0.46276(10) 0.0114(3) Uani 1 1 d . U . . .
C16 C 0.82054(12) 0.27128(16) 0.38833(11) 0.0150(3) Uani 1 1 d . U . . .
H16 H 0.841170 0.224088 0.326301 0.018 Uiso 1 1 calc R U . . .
C17 C 0.85796(12) 0.39954(16) 0.40661(11) 0.0172(3) Uani 1 1 d . U . . .
H17 H 0.903743 0.441162 0.356102 0.021 Uiso 1 1 calc R U . . .
C18 C 0.82899(12) 0.46851(16) 0.49878(11) 0.0166(3) Uani 1 1 d . U . . .
H18 H 0.856347 0.556111 0.510109 0.020 Uiso 1 1 calc R U . . .
C19 C 0.76110(12) 0.41187(15) 0.57421(11) 0.0141(3) Uani 1 1 d . U . . .
H19 H 0.742308 0.458819 0.637007 0.017 Uiso 1 1 calc R U . . .
C20 C 0.72176(11) 0.28386(14) 0.55422(10) 0.0112(3) Uani 1 1 d . U . . .
C1 C 0.4387(8) 0.7554(9) 0.8048(8) 0.0139(3) Uani 0.3591(15) 1 d . U P A 1
H1A H 0.372720 0.750268 0.849652 0.021 Uiso 0.3591(15) 1 calc R U P A 1
H1B H 0.413884 0.798821 0.735604 0.021 Uiso 0.3591(15) 1 calc R U P A 1
H1C H 0.501753 0.806260 0.843481 0.021 Uiso 0.3591(15) 1 calc R U P A 1
Br1 Br 0.43043(4) 0.77797(4) 0.81305(4) 0.01617(9) Uani 0.6409(15) 1 d . U P A
2


_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 C8 1.2153(17) . ?
N1 C8 1.3984(16) . ?
N1 C9 1.4164(18) . ?
N1 C20 1.4220(17) . ?
C2 C3 1.393(2) . ?
C2 C7 1.3949(19) . ?
C2 C1 1.600(9) . ?
C2 Br1 1.8659(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3997(18) . ?
C5 C6 1.3982(19) . ?
C5 C8 1.488(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.390(2) . ?
C9 C14 1.4087(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(2) . ?
C14 C15 1.449(2) . ?
C15 C16 1.3973(18) . ?
C15 C20 1.4091(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3913(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 123.56(12) . . ?
C8 N1 C20 128.19(12) . . ?
C9 N1 C20 108.14(11) . . ?
C3 C2 C7 120.73(14) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 Br1 118.82(11) . . ?
C7 C2 C1 119.0(4) . . ?
C7 C2 Br1 120.45(11) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.71(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.16(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C8 117.99(12) . . ?
C6 C5 C4 119.52(13) . . ?
C6 C5 C8 122.22(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.51(12) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 120.4 . . ?
C6 C7 C2 119.28(13) . . ?
C6 C7 H7 120.4 . . ?
O1 C8 N1 120.36(13) . . ?
O1 C8 C5 121.37(12) . . ?
N1 C8 C5 118.20(12) . . ?
C10 C9 N1 129.83(12) . . ?
C10 C9 C14 121.67(13) . . ?
C14 C9 N1 108.49(12) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 C9 117.33(13) . . ?
C11 C10 H10 121.3 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.81(15) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.43(14) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.87(13) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C15 107.36(12) . . ?
C13 C14 C9 119.89(13) . . ?
C13 C14 C15 132.70(12) . . ?
C16 C15 C14 132.17(13) . . ?
C16 C15 C20 119.92(13) . . ?
C20 C15 C14 107.69(11) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.80(13) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.64(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.60(14) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.49(13) . . ?
C20 C19 H19 121.3 . . ?
C15 C20 N1 108.15(12) . . ?
C19 C20 N1 130.06(12) . . ?
C19 C20 C15 121.53(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C9 C10 C11 178.63(13) . . . . ?
N1 C9 C14 C13 -178.23(12) . . . . ?
N1 C9 C14 C15 3.73(14) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C2 C7 C6 -2.6(2) . . . . ?
C3 C4 C5 C6 -3.0(2) . . . . ?
C3 C4 C5 C8 -177.15(12) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C4 C5 C8 O1 37.8(2) . . . . ?
C4 C5 C8 N1 -145.10(13) . . . . ?
C5 C6 C7 C2 1.6(2) . . . . ?
C6 C5 C8 O1 -136.11(15) . . . . ?
C6 C5 C8 N1 40.95(19) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C8 N1 C9 C10 0.6(2) . . . . ?
C8 N1 C9 C14 179.38(12) . . . . ?
C8 N1 C20 C15 179.26(12) . . . . ?
C8 N1 C20 C19 5.2(2) . . . . ?
C8 C5 C6 C7 175.10(12) . . . . ?
C9 N1 C8 O1 24.9(2) . . . . ?
C9 N1 C8 C5 -152.20(12) . . . . ?
C9 N1 C20 C15 3.15(14) . . . . ?
C9 N1 C20 C19 -170.89(14) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C9 C14 C15 C16 172.74(14) . . . . ?
C9 C14 C15 C20 -1.78(15) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
C10 C9 C14 C15 -177.40(12) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C12 C13 C14 C9 -0.7(2) . . . . ?
C12 C13 C14 C15 176.73(14) . . . . ?
C13 C14 C15 C16 -4.9(3) . . . . ?
C13 C14 C15 C20 -179.47(14) . . . . ?
C14 C9 C10 C11 0.0(2) . . . . ?
C14 C15 C16 C17 -173.81(14) . . . . ?
C14 C15 C20 N1 -0.85(14) . . . . ?
C14 C15 C20 C19 173.81(12) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C16 C15 C20 N1 -176.16(12) . . . . ?
C16 C15 C20 C19 -1.5(2) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 N1 175.06(13) . . . . ?
C18 C19 C20 C15 1.7(2) . . . . ?
C20 N1 C8 O1 -150.67(14) . . . . ?
C20 N1 C8 C5 32.24(19) . . . . ?
C20 N1 C9 C10 176.97(14) . . . . ?
C20 N1 C9 C14 -4.29(14) . . . . ?
C20 C15 C16 C17 0.2(2) . . . . ?
C1 C2 C3 C4 -178.0(4) . . . . ?
C1 C2 C7 C6 176.2(4) . . . . ?
Br1 C2 C3 C4 -179.08(11) . . . . ?
Br1 C2 C7 C6 177.30(10) . . . . ?

_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_mw454_a
_database_code_depnum_ccdc_archive 'CCDC 2116286'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.472 H13.417 Br0.528 N O'
_chemical_formula_sum            'C19.47 H13.41 Br0.53 N O'
_chemical_formula_weight         319.55
_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      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                   11.5657(6)
_cell_length_b                   10.1316(5)
_cell_length_c                   12.3187(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.031(2)
_cell_angle_gamma                90
_cell_volume                     1437.93(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.556
_cell_measurement_theta_min      2.316
_shelx_estimated_absorpt_T_max   0.725
_shelx_estimated_absorpt_T_min   0.578
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0548 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.7692.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             655
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.378
_exptl_crystal_size_min          0.222
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25444
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.556
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3798
_reflns_number_total             4414
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0299
_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)+(0.0348P)²+0.5788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0744
_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. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.60336(9) 0.13973(9) 0.78431(7) 0.0266(2) Uani 1 1 d . . . . .
N1 N 0.65889(8) 0.19866(9) 0.61885(7) 0.01497(18) Uani 1 1 d . . . . .
C2 C 0.48431(9) 0.61116(11) 0.78175(9) 0.0171(2) Uani 1 1 d . . . . .
C3 C 0.54452(10) 0.53848(12) 0.86421(9) 0.0187(2) Uani 1 1 d . . . . .
H3 H 0.556831 0.574001 0.935661 0.022 Uiso 1 1 calc R U . . .
C4 C 0.58657(10) 0.41406(12) 0.84195(9) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.625757 0.363385 0.898719 0.022 Uiso 1 1 calc R U . . .
C5 C 0.57149(9) 0.36311(11) 0.73642(9) 0.0149(2) Uani 1 1 d . . . . .
C6 C 0.50915(9) 0.43562(11) 0.65451(9) 0.0158(2) Uani 1 1 d . . . . .
H6 H 0.497338 0.400574 0.582864 0.019 Uiso 1 1 calc R U . . .
C7 C 0.46427(10) 0.55887(11) 0.67734(9) 0.0169(2) Uani 1 1 d . . . . .
H7 H 0.420193 0.607086 0.621991 0.020 Uiso 1 1 calc R U . . .
C8 C 0.61317(10) 0.22647(11) 0.71781(9) 0.0165(2) Uani 1 1 d . . . . .
C9 C 0.65593(9) 0.07185(10) 0.57050(9) 0.0153(2) Uani 1 1 d . . . . .
C10 C 0.60923(10) -0.04534(11) 0.60600(10) 0.0197(2) Uani 1 1 d . . . . .
H10 H 0.573880 -0.049853 0.672667 0.024 Uiso 1 1 calc R U . . .
C11 C 0.61648(10) -0.15556(12) 0.53980(11) 0.0234(2) Uani 1 1 d . . . . .
H11 H 0.585924 -0.237191 0.562252 0.028 Uiso 1 1 calc R U . . .
C12 C 0.66751(10) -0.14979(12) 0.44096(11) 0.0232(2) Uani 1 1 d . . . . .
H12 H 0.670635 -0.226875 0.397406 0.028 Uiso 1 1 calc R U . . .
C13 C 0.71356(10) -0.03226(11) 0.40621(9) 0.0193(2) Uani 1 1 d . . . . .
H13 H 0.747868 -0.027850 0.339005 0.023 Uiso 1 1 calc R U . . .
C14 C 0.70843(9) 0.07940(11) 0.47202(9) 0.0155(2) Uani 1 1 d . . . . .
C15 C 0.75197(9) 0.21264(10) 0.46245(9) 0.0147(2) Uani 1 1 d . . . . .
C16 C 0.82055(10) 0.27141(12) 0.38796(9) 0.0184(2) Uani 1 1 d . . . . .
H16 H 0.841098 0.224080 0.325913 0.022 Uiso 1 1 calc R U . . .
C17 C 0.85801(10) 0.40004(12) 0.40634(10) 0.0212(2) Uani 1 1 d . . . . .
H17 H 0.903946 0.441676 0.356007 0.025 Uiso 1 1 calc R U . . .
C18 C 0.82875(10) 0.46917(12) 0.49843(10) 0.0202(2) Uani 1 1 d . . . . .
H18 H 0.855759 0.557088 0.509611 0.024 Uiso 1 1 calc R U . . .
C19 C 0.76114(10) 0.41250(11) 0.57400(9) 0.0174(2) Uani 1 1 d . . . . .
H19 H 0.742552 0.459572 0.636862 0.021 Uiso 1 1 calc R U . . .
C20 C 0.72169(9) 0.28401(10) 0.55400(8) 0.0141(2) Uani 1 1 d . . . . .
C1 C 0.4457(10) 0.7551(10) 0.8120(10) 0.028(2) Uani 0.4724(12) 1 d . . P A 1
H1A H 0.413884 0.800793 0.745904 0.042 Uiso 0.4724(12) 1 calc R U P A 1
H1B H 0.512967 0.803915 0.845071 0.042 Uiso 0.4724(12) 1 calc R U P A 1
H1C H 0.386233 0.749897 0.863859 0.042 Uiso 0.4724(12) 1 calc R U P A 1
Br1 Br 0.43037(8) 0.77802(10) 0.81281(7) 0.02015(13) Uani 0.5276(12) 1 d . . P
A 2


_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 C8 1.2135(14) . ?
N1 C8 1.3993(13) . ?
N1 C9 1.4153(14) . ?
N1 C20 1.4196(13) . ?
C2 C3 1.3910(16) . ?
C2 C7 1.3916(15) . ?
C2 C1 1.579(9) . ?
C2 Br1 1.8535(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3872(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3953(15) . ?
C5 C6 1.3965(15) . ?
C5 C8 1.4903(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3905(15) . ?
C7 H7 0.9500 . ?
C9 C10 1.3908(15) . ?
C9 C14 1.4055(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3897(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.4000(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3874(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3960(15) . ?
C14 C15 1.4493(15) . ?
C15 C16 1.3977(15) . ?
C15 C20 1.4094(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.3857(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3997(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3913(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3942(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 123.53(9) . . ?
C8 N1 C20 128.22(9) . . ?
C9 N1 C20 108.11(8) . . ?
C3 C2 C7 120.37(10) . . ?
C3 C2 C1 116.8(4) . . ?
C3 C2 Br1 119.22(9) . . ?
C7 C2 C1 122.8(4) . . ?
C7 C2 Br1 120.41(9) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.90(10) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.20(10) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.54(10) . . ?
C4 C5 C8 118.12(10) . . ?
C6 C5 C8 122.07(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.30(10) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.61(10) . . ?
C6 C7 H7 120.2 . . ?
O1 C8 N1 120.48(10) . . ?
O1 C8 C5 121.21(10) . . ?
N1 C8 C5 118.24(9) . . ?
C10 C9 N1 129.67(10) . . ?
C10 C9 C14 121.80(10) . . ?
C14 C9 N1 108.51(9) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.15(11) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 121.91(11) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.44(11) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.64(11) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C15 107.48(9) . . ?
C13 C14 C9 120.04(10) . . ?
C13 C14 C15 132.45(10) . . ?
C16 C15 C14 132.18(10) . . ?
C16 C15 C20 120.13(10) . . ?
C20 C15 C14 107.48(9) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.73(10) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.58(10) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.73(11) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.48(10) . . ?
C20 C19 H19 121.3 . . ?
C15 C20 N1 108.25(9) . . ?
C19 C20 N1 130.16(10) . . ?
C19 C20 C15 121.33(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C9 C10 C11 178.46(11) . . . . ?
N1 C9 C14 C13 -178.02(10) . . . . ?
N1 C9 C14 C15 3.77(12) . . . . ?
C2 C3 C4 C5 1.80(17) . . . . ?
C3 C2 C7 C6 -2.77(16) . . . . ?
C3 C4 C5 C6 -2.94(16) . . . . ?
C3 C4 C5 C8 -177.10(10) . . . . ?
C4 C5 C6 C7 1.24(16) . . . . ?
C4 C5 C8 O1 38.07(16) . . . . ?
C4 C5 C8 N1 -145.09(10) . . . . ?
C5 C6 C7 C2 1.61(16) . . . . ?
C6 C5 C8 O1 -135.92(12) . . . . ?
C6 C5 C8 N1 40.91(15) . . . . ?
C7 C2 C3 C4 1.08(17) . . . . ?
C8 N1 C9 C10 0.99(18) . . . . ?
C8 N1 C9 C14 179.64(10) . . . . ?
C8 N1 C20 C15 179.01(10) . . . . ?
C8 N1 C20 C19 4.94(19) . . . . ?
C8 C5 C6 C7 175.15(10) . . . . ?
C9 N1 C8 O1 24.51(17) . . . . ?
C9 N1 C8 C5 -152.35(10) . . . . ?
C9 N1 C20 C15 3.28(12) . . . . ?
C9 N1 C20 C19 -170.78(11) . . . . ?
C9 C10 C11 C12 -0.54(18) . . . . ?
C9 C14 C15 C16 172.78(12) . . . . ?
C9 C14 C15 C20 -1.73(12) . . . . ?
C10 C9 C14 C13 0.76(17) . . . . ?
C10 C9 C14 C15 -177.46(10) . . . . ?
C10 C11 C12 C13 0.39(19) . . . . ?
C11 C12 C13 C14 0.35(18) . . . . ?
C12 C13 C14 C9 -0.90(17) . . . . ?
C12 C13 C14 C15 176.79(11) . . . . ?
C13 C14 C15 C16 -5.1(2) . . . . ?
C13 C14 C15 C20 -179.64(12) . . . . ?
C14 C9 C10 C11 -0.03(17) . . . . ?
C14 C15 C16 C17 -173.71(11) . . . . ?
C14 C15 C20 N1 -0.95(12) . . . . ?
C14 C15 C20 C19 173.74(10) . . . . ?
C15 C16 C17 C18 0.71(17) . . . . ?
C16 C15 C20 N1 -176.25(10) . . . . ?
C16 C15 C20 C19 -1.56(16) . . . . ?
C16 C17 C18 C19 -0.37(18) . . . . ?
C17 C18 C19 C20 -0.92(17) . . . . ?
C18 C19 C20 N1 175.27(11) . . . . ?
C18 C19 C20 C15 1.87(16) . . . . ?
C20 N1 C8 O1 -150.62(11) . . . . ?
C20 N1 C8 C5 32.53(16) . . . . ?
C20 N1 C9 C10 176.96(11) . . . . ?
C20 N1 C9 C14 -4.39(12) . . . . ?
C20 C15 C16 C17 0.23(16) . . . . ?
C1 C2 C3 C4 -176.5(5) . . . . ?
C1 C2 C7 C6 174.7(5) . . . . ?
Br1 C2 C3 C4 -179.28(9) . . . . ?
Br1 C2 C7 C6 177.59(9) . . . . ?

_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_mw445_a
_database_code_depnum_ccdc_archive 'CCDC 2116285'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.44 H13.32 Br0.56 N O'
_chemical_formula_sum            'C19.44 H13.32 Br0.56 N O'
_chemical_formula_weight         321.66
_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      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                   11.5680(7)
_cell_length_b                   10.1429(5)
_cell_length_c                   12.3305(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.097(2)
_cell_angle_gamma                90
_cell_volume                     1441.05(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.576
_shelx_estimated_absorpt_T_min   0.575
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0488 before and 0.0321 after correction.
The Ratio of minimum to maximum transmission is 0.8928.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             658
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.379
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27288
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_min         2.314
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3853
_reflns_number_total             4402
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     351
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      0.984
_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)+(0.0303P)²+0.6733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0696
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C3(H3), C16(H16), C19(H19), C4(H4), C13(H13), C17(H17),
 C18(H18), C10(H10), C12(H12), C11(H11)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.56955(8) 0.22198(8) 0.18719(6) 0.02024(11) Uani 0.5601(12) 1 d . U P A
1
O1 O 0.39663(8) 0.86035(9) 0.21559(7) 0.0267(2) Uani 1 1 d . U . . .
N1 N 0.34112(8) 0.80134(9) 0.38105(7) 0.01503(18) Uani 1 1 d . U . . .
C20 C 0.27829(9) 0.71598(11) 0.44603(8) 0.01427(19) Uani 1 1 d . U . . .
C14 C 0.29164(9) 0.92061(11) 0.52801(8) 0.0156(2) Uani 1 1 d . U . . .
C7 C 0.53591(9) 0.44146(11) 0.32274(9) 0.0170(2) Uani 1 1 d . U . . .
H7 H 0.580115 0.393390 0.378061 0.020 Uiso 1 1 calc R U . . .
C5 C 0.42855(9) 0.63695(11) 0.26353(8) 0.0149(2) Uani 1 1 d . U . . .
C15 C 0.24806(9) 0.78740(11) 0.53751(8) 0.01481(19) Uani 1 1 d . U . . .
C6 C 0.49094(9) 0.56458(11) 0.34547(8) 0.0160(2) Uani 1 1 d . U . . .
H6 H 0.502711 0.599618 0.417052 0.019 Uiso 1 1 calc R U . . .
C3 C 0.45546(9) 0.46152(12) 0.13572(9) 0.0187(2) Uani 1 1 d . U . . .
H3 H 0.443170 0.425977 0.064341 0.022 Uiso 1 1 calc R U . . .
C9 C 0.34414(9) 0.92802(11) 0.42949(8) 0.0155(2) Uani 1 1 d . U . . .
C16 C 0.17946(9) 0.72849(12) 0.61198(9) 0.0184(2) Uani 1 1 d . U . . .
H16 H 0.158967 0.775760 0.673966 0.022 Uiso 1 1 calc R U . . .
C8 C 0.38687(9) 0.77358(11) 0.28215(8) 0.0166(2) Uani 1 1 d . U . . .
C19 C 0.23888(9) 0.58766(11) 0.42592(9) 0.0174(2) Uani 1 1 d . U . . .
H19 H 0.257438 0.540704 0.363094 0.021 Uiso 1 1 calc R U . . .
C4 C 0.41334(9) 0.58595(12) 0.15799(8) 0.0180(2) Uani 1 1 d . U . . .
H4 H 0.374066 0.636536 0.101258 0.022 Uiso 1 1 calc R U . . .
C13 C 0.28640(10) 1.03224(12) 0.59371(9) 0.0195(2) Uani 1 1 d . U . . .
H13 H 0.252051 1.027897 0.660797 0.023 Uiso 1 1 calc R U . . .
C2 C 0.51571(9) 0.38910(11) 0.21831(9) 0.0171(2) Uani 1 1 d . U . . .
C17 C 0.14201(10) 0.60007(12) 0.59367(9) 0.0213(2) Uani 1 1 d . U . . .
H17 H 0.096160 0.558517 0.643992 0.026 Uiso 1 1 calc R U . . .
C18 C 0.17117(10) 0.53085(12) 0.50153(9) 0.0204(2) Uani 1 1 d . U . . .
H18 H 0.144125 0.443044 0.490335 0.025 Uiso 1 1 calc R U . . .
C10 C 0.39075(10) 1.04527(12) 0.39380(9) 0.0198(2) Uani 1 1 d . U . . .
H10 H 0.425929 1.049804 0.327152 0.024 Uiso 1 1 calc R U . . .
C12 C 0.33245(10) 1.14970(12) 0.55891(10) 0.0233(2) Uani 1 1 d . U . . .
H12 H 0.329336 1.226723 0.602387 0.028 Uiso 1 1 calc R U . . .
C11 C 0.38350(10) 1.15544(12) 0.46010(11) 0.0233(2) Uani 1 1 d . U . . .
H11 H 0.414070 1.236978 0.437728 0.028 Uiso 1 1 calc R U . . .
C1 C 0.5556(11) 0.2452(10) 0.1883(10) 0.028(2) Uani 0.4399(12) 1 d . U P A 2
H1A H 0.615280 0.250893 0.136773 0.042 Uiso 0.4399(12) 1 calc R U P A 2
H1B H 0.488811 0.195794 0.154941 0.042 Uiso 0.4399(12) 1 calc R U P A 2
H1C H 0.587460 0.199804 0.254466 0.042 Uiso 0.4399(12) 1 calc R U P A 2


_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 C2 1.8576(14) . ?
O1 C8 1.2156(13) . ?
N1 C20 1.4225(13) . ?
N1 C9 1.4161(14) . ?
N1 C8 1.4003(13) . ?
C20 C15 1.4105(14) . ?
C20 C19 1.3940(16) . ?
C14 C15 1.4505(15) . ?
C14 C9 1.4076(14) . ?
C14 C13 1.3967(15) . ?
C7 H7 0.9500 . ?
C7 C6 1.3909(16) . ?
C7 C2 1.3934(15) . ?
C5 C6 1.3967(15) . ?
C5 C8 1.4918(15) . ?
C5 C4 1.3970(14) . ?
C15 C16 1.3997(14) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.3891(16) . ?
C3 C2 1.3915(16) . ?
C9 C10 1.3932(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3849(17) . ?
C19 H19 0.9500 . ?
C19 C18 1.3945(15) . ?
C4 H4 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.3885(17) . ?
C2 C1 1.585(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.4020(16) . ?
C18 H18 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.3915(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.4016(17) . ?
C11 H11 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C9 N1 C20 108.02(8) . . ?
C8 N1 C20 128.29(9) . . ?
C8 N1 C9 123.56(9) . . ?
C15 C20 N1 108.26(9) . . ?
C19 C20 N1 130.05(10) . . ?
C19 C20 C15 121.42(9) . . ?
C9 C14 C15 107.40(9) . . ?
C13 C14 C15 132.46(10) . . ?
C13 C14 C9 120.10(10) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C2 119.57(10) . . ?
C2 C7 H7 120.2 . . ?
C6 C5 C8 122.02(9) . . ?
C6 C5 C4 119.57(10) . . ?
C4 C5 C8 118.14(9) . . ?
C20 C15 C14 107.53(9) . . ?
C16 C15 C20 120.05(10) . . ?
C16 C15 C14 132.22(10) . . ?
C7 C6 C5 120.30(10) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.78(10) . . ?
C2 C3 H3 120.1 . . ?
C14 C9 N1 108.62(9) . . ?
C10 C9 N1 129.57(10) . . ?
C10 C9 C14 121.80(10) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.81(10) . . ?
C17 C16 H16 120.6 . . ?
O1 C8 N1 120.49(10) . . ?
O1 C8 C5 121.20(9) . . ?
N1 C8 C5 118.24(9) . . ?
C20 C19 H19 121.3 . . ?
C20 C19 C18 117.46(10) . . ?
C18 C19 H19 121.3 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.21(10) . . ?
C3 C4 H4 119.9 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.60(10) . . ?
C12 C13 H13 120.7 . . ?
C7 C2 Br1 120.46(9) . . ?
C7 C2 C1 122.6(4) . . ?
C3 C2 Br1 119.07(9) . . ?
C3 C2 C7 120.47(10) . . ?
C3 C2 C1 116.9(4) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.58(10) . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 121.65(11) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C9 C10 H10 121.5 . . ?
C11 C10 C9 117.04(10) . . ?
C11 C10 H10 121.5 . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.47(11) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 C12 121.97(11) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C20 C15 C14 0.90(11) . . . . ?
N1 C20 C15 C16 176.25(9) . . . . ?
N1 C20 C19 C18 -175.24(11) . . . . ?
N1 C9 C10 C11 -178.54(11) . . . . ?
C20 N1 C9 C14 4.32(12) . . . . ?
C20 N1 C9 C10 -176.85(11) . . . . ?
C20 N1 C8 O1 150.64(11) . . . . ?
C20 N1 C8 C5 -32.44(15) . . . . ?
C20 C15 C16 C17 -0.26(16) . . . . ?
C20 C19 C18 C17 0.91(17) . . . . ?
C14 C15 C16 C17 173.75(11) . . . . ?
C14 C9 C10 C11 0.16(16) . . . . ?
C14 C13 C12 C11 -0.29(18) . . . . ?
C15 C20 C19 C18 -1.91(16) . . . . ?
C15 C14 C9 N1 -3.73(12) . . . . ?
C15 C14 C9 C10 177.33(10) . . . . ?
C15 C14 C13 C12 -176.73(11) . . . . ?
C15 C16 C17 C18 -0.73(17) . . . . ?
C6 C7 C2 Br1 -177.47(9) . . . . ?
C6 C7 C2 C3 2.87(16) . . . . ?
C6 C7 C2 C1 -175.2(6) . . . . ?
C6 C5 C8 O1 135.95(12) . . . . ?
C6 C5 C8 N1 -40.95(15) . . . . ?
C6 C5 C4 C3 2.89(16) . . . . ?
C9 N1 C20 C15 -3.20(11) . . . . ?
C9 N1 C20 C19 170.81(11) . . . . ?
C9 N1 C8 O1 -24.61(16) . . . . ?
C9 N1 C8 C5 152.31(10) . . . . ?
C9 C14 C15 C20 1.75(12) . . . . ?
C9 C14 C15 C16 -172.82(11) . . . . ?
C9 C14 C13 C12 0.83(16) . . . . ?
C9 C10 C11 C12 0.40(18) . . . . ?
C16 C17 C18 C19 0.41(18) . . . . ?
C8 N1 C20 C15 -179.04(10) . . . . ?
C8 N1 C20 C19 -5.03(18) . . . . ?
C8 N1 C9 C14 -179.60(9) . . . . ?
C8 N1 C9 C10 -0.77(18) . . . . ?
C8 C5 C6 C7 -175.10(10) . . . . ?
C8 C5 C4 C3 177.07(10) . . . . ?
C19 C20 C15 C14 -173.73(10) . . . . ?
C19 C20 C15 C16 1.62(16) . . . . ?
C4 C5 C6 C7 -1.15(16) . . . . ?
C4 C5 C8 O1 -38.08(16) . . . . ?
C4 C5 C8 N1 145.02(10) . . . . ?
C4 C3 C2 Br1 179.18(9) . . . . ?
C4 C3 C2 C7 -1.16(16) . . . . ?
C4 C3 C2 C1 177.0(5) . . . . ?
C13 C14 C15 C20 179.53(11) . . . . ?
C13 C14 C15 C16 5.0(2) . . . . ?
C13 C14 C9 N1 178.15(10) . . . . ?
C13 C14 C9 C10 -0.79(16) . . . . ?
C13 C12 C11 C10 -0.34(19) . . . . ?
C2 C7 C6 C5 -1.71(16) . . . . ?
C2 C3 C4 C5 -1.74(16) . . . . ?

_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_mw462_a
_database_code_depnum_ccdc_archive 'CCDC 2116287'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.557 H13.671 Br0.443 N O'
_chemical_formula_sum            'C19.56 H13.67 Br0.44 N O'
_chemical_formula_weight         314.04
_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      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                   11.5850(7)
_cell_length_b                   10.1100(6)
_cell_length_c                   12.3005(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.882(4)
_cell_angle_gamma                90
_cell_volume                     1435.46(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8114
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.622
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1563 before and 0.0880 after correction.
The Ratio of minimum to maximum transmission is 0.6896.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             646
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.322
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25359
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.701
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3274
_reflns_number_total             4401
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.192
_refine_diff_density_min         -1.146
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     351
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.006
_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)+(0.1371P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2147
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C7)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.60329(18) 0.13943(19) 0.78392(14) 0.0307(5) Uani 1 1 d . U . . .
N1 N 0.65874(17) 0.19853(19) 0.61833(15) 0.0178(4) Uani 1 1 d . U . . .
C2 C 0.4844(2) 0.6125(2) 0.78205(18) 0.0204(3) Uani 1 1 d . U . . .
C3 C 0.5449(2) 0.5389(2) 0.86443(18) 0.0204(3) Uani 1 1 d . U . . .
H3 H 0.557514 0.574354 0.935989 0.024 Uiso 1 1 calc R U . . .
C4 C 0.58645(19) 0.4143(2) 0.84181(17) 0.0201(5) Uani 1 1 d . U . . .
H4 H 0.625265 0.363355 0.898629 0.024 Uiso 1 1 calc R U . . .
C5 C 0.57174(19) 0.3631(2) 0.73623(17) 0.0175(4) Uani 1 1 d . U . . .
C6 C 0.50942(19) 0.4356(2) 0.65475(17) 0.0178(4) Uani 1 1 d . U . . .
H6 H 0.497508 0.400456 0.583046 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4646(2) 0.5588(2) 0.67760(17) 0.0204(3) Uani 1 1 d . U . . .
H7 H 0.420457 0.606696 0.622112 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6130(2) 0.2262(2) 0.71772(17) 0.0193(5) Uani 1 1 d . U . . .
C9 C 0.65622(19) 0.0722(2) 0.56999(17) 0.0179(4) Uani 1 1 d . U . . .
C10 C 0.6093(2) -0.0456(2) 0.60558(19) 0.0223(5) Uani 1 1 d . U . . .
H10 H 0.574126 -0.050229 0.672459 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6163(2) -0.1556(3) 0.5393(2) 0.0270(5) Uani 1 1 d . U . . .
H11 H 0.585347 -0.237332 0.561380 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6679(2) -0.1492(3) 0.4406(2) 0.0268(5) Uani 1 1 d . U . . .
H12 H 0.671535 -0.226442 0.396982 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7135(2) -0.0321(2) 0.40592(19) 0.0225(5) Uani 1 1 d . U . . .
H13 H 0.747611 -0.027678 0.338460 0.027 Uiso 1 1 calc R U . . .
C14 C 0.70861(18) 0.0797(2) 0.47182(17) 0.0175(4) Uani 1 1 d . U . . .
C15 C 0.7522(2) 0.2129(2) 0.46256(17) 0.0172(4) Uani 1 1 d . U . . .
C16 C 0.8205(2) 0.2719(2) 0.38797(18) 0.0206(5) Uani 1 1 d . U . . .
H16 H 0.840831 0.224581 0.325699 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8578(2) 0.4000(3) 0.40603(19) 0.0244(5) Uani 1 1 d . U . . .
H17 H 0.903612 0.441521 0.355415 0.029 Uiso 1 1 calc R U . . .
C18 C 0.8288(2) 0.4696(2) 0.49823(19) 0.0230(5) Uani 1 1 d . U . . .
H18 H 0.855949 0.557583 0.509476 0.028 Uiso 1 1 calc R U . . .
C19 C 0.76117(19) 0.4127(2) 0.57360(17) 0.0197(5) Uani 1 1 d . U . . .
H19 H 0.742259 0.459956 0.636457 0.024 Uiso 1 1 calc R U . . .
C20 C 0.72207(19) 0.2840(2) 0.55374(17) 0.0168(4) Uani 1 1 d . U . . .
C1 C 0.4436(8) 0.7562(9) 0.8048(7) 0.0204(3) Uani 0.557(2) 1 d . U P A 1
H1A H 0.410241 0.796156 0.736599 0.031 Uiso 0.557(2) 1 calc R U P A 1
H1B H 0.509895 0.809013 0.834419 0.031 Uiso 0.557(2) 1 calc R U P A 1
H1C H 0.384888 0.753784 0.857643 0.031 Uiso 0.557(2) 1 calc R U P A 1
Br1 Br 0.43067(8) 0.77809(8) 0.81355(8) 0.0241(2) Uani 0.443(2) 1 d . U P A 2


_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 C8 1.209(3) . ?
N1 C8 1.401(3) . ?
N1 C9 1.408(3) . ?
N1 C20 1.420(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.395(3) . ?
C2 C1 1.561(9) . ?
C2 Br1 1.839(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(3) . ?
C5 C6 1.393(3) . ?
C5 C8 1.488(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.395(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(3) . ?
C14 C15 1.446(3) . ?
C15 C16 1.395(3) . ?
C15 C20 1.402(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 123.62(19) . . ?
C8 N1 C20 128.2(2) . . ?
C9 N1 C20 108.00(17) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 Br1 119.32(17) . . ?
C7 C2 C3 119.6(2) . . ?
C7 C2 C1 119.9(4) . . ?
C7 C2 Br1 121.05(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C8 118.2(2) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 C8 122.21(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
O1 C8 N1 120.4(2) . . ?
O1 C8 C5 121.5(2) . . ?
N1 C8 C5 117.99(19) . . ?
C10 C9 N1 129.5(2) . . ?
C10 C9 C14 121.8(2) . . ?
C14 C9 N1 108.69(19) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(2) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C15 107.39(19) . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 C15 132.6(2) . . ?
C16 C15 C14 132.2(2) . . ?
C16 C15 C20 120.0(2) . . ?
C20 C15 C14 107.58(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 121.2 . . ?
C18 C19 C20 117.6(2) . . ?
C20 C19 H19 121.2 . . ?
C15 C20 N1 108.14(19) . . ?
C19 C20 N1 130.3(2) . . ?
C19 C20 C15 121.4(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C9 C10 C11 178.1(2) . . . . ?
N1 C9 C14 C13 -177.8(2) . . . . ?
N1 C9 C14 C15 4.0(2) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C3 C2 C7 C6 -2.9(3) . . . . ?
C3 C4 C5 C6 -3.4(3) . . . . ?
C3 C4 C5 C8 -177.1(2) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C4 C5 C8 O1 37.9(3) . . . . ?
C4 C5 C8 N1 -145.2(2) . . . . ?
C5 C6 C7 C2 1.7(3) . . . . ?
C6 C5 C8 O1 -135.7(3) . . . . ?
C6 C5 C8 N1 41.3(3) . . . . ?
C7 C2 C3 C4 1.0(3) . . . . ?
C8 N1 C9 C10 1.3(4) . . . . ?
C8 N1 C9 C14 179.8(2) . . . . ?
C8 N1 C20 C15 178.7(2) . . . . ?
C8 N1 C20 C19 4.2(4) . . . . ?
C8 C5 C6 C7 174.9(2) . . . . ?
C9 N1 C8 O1 24.3(4) . . . . ?
C9 N1 C8 C5 -152.6(2) . . . . ?
C9 N1 C20 C15 3.6(2) . . . . ?
C9 N1 C20 C19 -171.0(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C14 C15 C16 173.1(2) . . . . ?
C9 C14 C15 C20 -1.8(2) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C10 C9 C14 C15 -177.3(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C12 C13 C14 C15 176.5(2) . . . . ?
C13 C14 C15 C16 -4.8(4) . . . . ?
C13 C14 C15 C20 -179.7(2) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C14 C15 C16 C17 -174.0(2) . . . . ?
C14 C15 C20 N1 -1.1(2) . . . . ?
C14 C15 C20 C19 174.1(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C15 C20 N1 -176.74(19) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C18 C19 C20 N1 175.6(2) . . . . ?
C18 C19 C20 C15 1.7(3) . . . . ?
C20 N1 C8 O1 -150.2(2) . . . . ?
C20 N1 C8 C5 32.9(3) . . . . ?
C20 N1 C9 C10 176.7(2) . . . . ?
C20 N1 C9 C14 -4.7(2) . . . . ?
C20 C15 C16 C17 0.4(3) . . . . ?
C1 C2 C3 C4 -176.4(4) . . . . ?
C1 C2 C7 C6 174.5(4) . . . . ?
Br1 C2 C3 C4 -179.66(18) . . . . ?
Br1 C2 C7 C6 177.78(18) . . . . ?

_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_mw414_a
_database_code_depnum_ccdc_archive 'CCDC 2116289'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-01-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.813 H14.438 Br0.187 N O'
_chemical_formula_sum            'C19.81 H14.44 Br0.19 N O'
_chemical_formula_weight         297.49
_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      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                   11.6030(8)
_cell_length_b                   10.0711(6)
_cell_length_c                   12.3038(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.846(2)
_cell_angle_gamma                90
_cell_volume                     1432.62(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.834
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0925 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8082.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.312
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25717
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.567
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3739
_reflns_number_total             4386
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.041
_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)+(0.0554P)²+0.3695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1020
_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. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.60339(7) 0.13891(8) 0.78408(6) 0.02308(18) Uani 1 1 d . . . . .
N1 N 0.65906(7) 0.19892(8) 0.61805(6) 0.01325(16) Uani 1 1 d . . . . .
C2 C 0.48468(8) 0.61559(10) 0.78259(8) 0.01551(18) Uani 1 1 d . . . . .
C3 C 0.54474(8) 0.54084(10) 0.86440(8) 0.01673(19) Uani 1 1 d . . . . .
H3 H 0.557092 0.576109 0.936049 0.020 Uiso 1 1 calc R U . . .
C4 C 0.58669(8) 0.41528(10) 0.84217(8) 0.01582(19) Uani 1 1 d . . . . .
H4 H 0.625473 0.364278 0.899032 0.019 Uiso 1 1 calc R U . . .
C5 C 0.57197(8) 0.36398(9) 0.73655(7) 0.01318(17) Uani 1 1 d . . . . .
C6 C 0.51008(8) 0.43721(10) 0.65452(7) 0.01415(18) Uani 1 1 d . . . . .
H6 H 0.498498 0.402220 0.582723 0.017 Uiso 1 1 calc R U . . .
C7 C 0.46545(8) 0.56121(10) 0.67788(8) 0.01547(18) Uani 1 1 d . . . . .
H7 H 0.421573 0.609381 0.622355 0.019 Uiso 1 1 calc R U . . .
C8 C 0.61329(8) 0.22668(10) 0.71748(8) 0.01442(18) Uani 1 1 d . . . . .
C9 C 0.65615(8) 0.07135(9) 0.56950(8) 0.01356(18) Uani 1 1 d . . . . .
C10 C 0.60954(8) -0.04685(10) 0.60486(8) 0.01746(19) Uani 1 1 d . . . . .
H10 H 0.574239 -0.051600 0.671661 0.021 Uiso 1 1 calc R U . . .
C11 C 0.61681(9) -0.15769(10) 0.53835(9) 0.0203(2) Uani 1 1 d . . . . .
H11 H 0.586406 -0.239887 0.560805 0.024 Uiso 1 1 calc R U . . .
C12 C 0.66774(9) -0.15156(11) 0.43912(9) 0.0203(2) Uani 1 1 d . . . . .
H12 H 0.670619 -0.228955 0.395289 0.024 Uiso 1 1 calc R U . . .
C13 C 0.71402(8) -0.03326(10) 0.40435(8) 0.01716(19) Uani 1 1 d . . . . .
H13 H 0.748371 -0.028710 0.337043 0.021 Uiso 1 1 calc R U . . .
C14 C 0.70890(8) 0.07892(10) 0.47065(8) 0.01372(18) Uani 1 1 d . . . . .
C15 C 0.75242(8) 0.21307(9) 0.46131(7) 0.01309(17) Uani 1 1 d . . . . .
C16 C 0.82099(8) 0.27235(10) 0.38674(8) 0.01636(19) Uani 1 1 d . . . . .
H16 H 0.841903 0.224595 0.324792 0.020 Uiso 1 1 calc R U . . .
C17 C 0.85801(8) 0.40222(11) 0.40477(8) 0.0184(2) Uani 1 1 d . . . . .
H17 H 0.903502 0.444343 0.354121 0.022 Uiso 1 1 calc R U . . .
C18 C 0.82860(8) 0.47150(10) 0.49733(8) 0.01774(19) Uani 1 1 d . . . . .
H18 H 0.855382 0.559971 0.508638 0.021 Uiso 1 1 calc R U . . .
C19 C 0.76108(8) 0.41401(10) 0.57322(8) 0.01523(18) Uani 1 1 d . . . . .
H19 H 0.742439 0.461138 0.636288 0.018 Uiso 1 1 calc R U . . .
C20 C 0.72200(8) 0.28480(9) 0.55303(7) 0.01280(17) Uani 1 1 d . . . . .
C1 C 0.4418(6) 0.7571(6) 0.8088(6) 0.0254(14) Uani 0.8125(9) 1 d . . P A 1
H1A H 0.406718 0.798480 0.741845 0.038 Uiso 0.8125(9) 1 calc R U P A 1
H1B H 0.507337 0.810981 0.838594 0.038 Uiso 0.8125(9) 1 calc R U P A 1
H1C H 0.384161 0.751263 0.862419 0.038 Uiso 0.8125(9) 1 calc R U P A 1
Br1 Br 0.4310(3) 0.7782(3) 0.8135(2) 0.0184(3) Uani 0.1875(9) 1 d . . P A 2


_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 C8 1.2173(12) . ?
N1 C8 1.4025(11) . ?
N1 C9 1.4160(12) . ?
N1 C20 1.4213(11) . ?
C2 C3 1.3954(14) . ?
C2 C7 1.4003(13) . ?
C2 C1 1.553(6) . ?
C2 Br1 1.804(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.3904(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3955(13) . ?
C5 C6 1.3984(13) . ?
C5 C8 1.4886(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.3913(13) . ?
C7 H7 0.9500 . ?
C9 C10 1.3923(13) . ?
C9 C14 1.4091(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.3908(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.4020(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3891(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3977(13) . ?
C14 C15 1.4503(13) . ?
C15 C16 1.3980(13) . ?
C15 C20 1.4097(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.3886(15) . ?
C17 H17 0.9500 . ?
C17 C18 1.4021(14) . ?
C18 H18 0.9500 . ?
C18 C19 1.3945(13) . ?
C19 H19 0.9500 . ?
C19 C20 1.3934(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 123.47(8) . . ?
C8 N1 C20 128.32(8) . . ?
C9 N1 C20 108.05(7) . . ?
C3 C2 C7 118.93(9) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 Br1 119.86(12) . . ?
C7 C2 C1 121.4(3) . . ?
C7 C2 Br1 121.20(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.70(9) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.16(9) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.47(9) . . ?
C4 C5 C8 118.35(8) . . ?
C6 C5 C8 121.92(8) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.11(9) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.53(9) . . ?
C6 C7 H7 119.7 . . ?
O1 C8 N1 120.44(9) . . ?
O1 C8 C5 121.23(8) . . ?
N1 C8 C5 118.26(8) . . ?
C10 C9 N1 129.79(9) . . ?
C10 C9 C14 121.63(9) . . ?
C14 C9 N1 108.56(8) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.25(9) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.87(10) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.55(10) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.48(9) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C15 107.36(8) . . ?
C13 C14 C9 120.20(9) . . ?
C13 C14 C15 132.41(9) . . ?
C16 C15 C14 132.15(9) . . ?
C16 C15 C20 120.09(9) . . ?
C20 C15 C14 107.55(8) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.88(9) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.34(9) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.76(9) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 121.3 . . ?
C20 C19 C18 117.46(9) . . ?
C20 C19 H19 121.3 . . ?
C15 C20 N1 108.30(8) . . ?
C19 C20 N1 130.01(8) . . ?
C19 C20 C15 121.44(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C9 C10 C11 178.43(9) . . . . ?
N1 C9 C14 C13 -177.90(8) . . . . ?
N1 C9 C14 C15 3.76(10) . . . . ?
C2 C3 C4 C5 1.84(14) . . . . ?
C3 C2 C7 C6 -2.93(14) . . . . ?
C3 C4 C5 C6 -2.96(14) . . . . ?
C3 C4 C5 C8 -177.15(8) . . . . ?
C4 C5 C6 C7 1.14(14) . . . . ?
C4 C5 C8 O1 37.97(13) . . . . ?
C4 C5 C8 N1 -145.10(9) . . . . ?
C5 C6 C7 C2 1.82(14) . . . . ?
C6 C5 C8 O1 -136.07(10) . . . . ?
C6 C5 C8 N1 40.85(12) . . . . ?
C7 C2 C3 C4 1.11(14) . . . . ?
C8 N1 C9 C10 1.02(15) . . . . ?
C8 N1 C9 C14 179.77(8) . . . . ?
C8 N1 C20 C15 178.86(9) . . . . ?
C8 N1 C20 C19 4.68(16) . . . . ?
C8 C5 C6 C7 175.12(8) . . . . ?
C9 N1 C8 O1 24.47(14) . . . . ?
C9 N1 C8 C5 -152.48(9) . . . . ?
C9 N1 C20 C15 3.25(10) . . . . ?
C9 N1 C20 C19 -170.92(9) . . . . ?
C9 C10 C11 C12 -0.61(15) . . . . ?
C9 C14 C15 C16 172.85(10) . . . . ?
C9 C14 C15 C20 -1.74(10) . . . . ?
C10 C9 C14 C13 0.98(14) . . . . ?
C10 C9 C14 C15 -177.37(8) . . . . ?
C10 C11 C12 C13 0.61(16) . . . . ?
C11 C12 C13 C14 0.20(15) . . . . ?
C12 C13 C14 C9 -0.97(14) . . . . ?
C12 C13 C14 C15 176.89(10) . . . . ?
C13 C14 C15 C16 -5.21(18) . . . . ?
C13 C14 C15 C20 -179.80(10) . . . . ?
C14 C9 C10 C11 -0.17(14) . . . . ?
C14 C15 C16 C17 -174.11(10) . . . . ?
C14 C15 C20 N1 -0.93(10) . . . . ?
C14 C15 C20 C19 173.84(8) . . . . ?
C15 C16 C17 C18 1.12(15) . . . . ?
C16 C15 C20 N1 -176.30(8) . . . . ?
C16 C15 C20 C19 -1.53(14) . . . . ?
C16 C17 C18 C19 -0.63(15) . . . . ?
C17 C18 C19 C20 -0.92(15) . . . . ?
C18 C19 C20 N1 175.50(9) . . . . ?
C18 C19 C20 C15 1.98(14) . . . . ?
C20 N1 C8 O1 -150.51(10) . . . . ?
C20 N1 C8 C5 32.53(13) . . . . ?
C20 N1 C9 C10 176.88(9) . . . . ?
C20 N1 C9 C14 -4.37(10) . . . . ?
C20 C15 C16 C17 -0.07(14) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C1 C2 C7 C6 176.4(3) . . . . ?
Br1 C2 C3 C4 179.96(13) . . . . ?
Br1 C2 C7 C6 178.24(13) . . . . ?

_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_mw416_a
_database_code_depnum_ccdc_archive 'CCDC 2116290'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.912 H14.736 Br0.088 N O'
_chemical_formula_sum            'C19.91 H14.74 Br0.09 N O'
_chemical_formula_weight         291.01
_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      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                   11.6141(6)
_cell_length_b                   10.0515(5)
_cell_length_c                   12.2961(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.7450(10)
_cell_angle_gamma                90
_cell_volume                     1430.52(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.588
_cell_measurement_theta_min      2.318
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0509 before and 0.0336 after correction.
The Ratio of minimum to maximum transmission is 0.9605.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             609
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.378
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25534
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.616
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3846
_reflns_number_total             4395
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.040
_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)+(0.0592P)²+0.4848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1071
_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. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.60339(7) 0.86158(8) 0.78367(6) 0.02219(17) Uani 1 1 d . . . . .
N1 N 0.65909(7) 0.80114(8) 0.61776(6) 0.01259(15) Uani 1 1 d . . . . .
C2 C 0.48492(8) 0.38322(9) 0.78275(7) 0.01469(17) Uani 1 1 d . . . . .
C3 C 0.54485(8) 0.45873(10) 0.86443(7) 0.01598(18) Uani 1 1 d . . . . .
H3 H 0.557111 0.423579 0.936173 0.019 Uiso 1 1 calc R U . . .
C4 C 0.58674(8) 0.58446(10) 0.84222(7) 0.01496(17) Uani 1 1 d . . . . .
H4 H 0.625473 0.635556 0.899054 0.018 Uiso 1 1 calc R U . . .
C5 C 0.57195(7) 0.63584(9) 0.73638(7) 0.01245(16) Uani 1 1 d . . . . .
C6 C 0.51030(8) 0.56214(9) 0.65455(7) 0.01335(16) Uani 1 1 d . . . . .
H6 H 0.498806 0.597001 0.582658 0.016 Uiso 1 1 calc R U . . .
C7 C 0.46575(8) 0.43793(9) 0.67808(7) 0.01455(17) Uani 1 1 d . . . . .
H7 H 0.421872 0.389732 0.622579 0.017 Uiso 1 1 calc R U . . .
C8 C 0.61328(8) 0.77339(9) 0.71734(7) 0.01383(17) Uani 1 1 d . . . . .
C9 C 0.65629(7) 0.92887(9) 0.56914(7) 0.01289(16) Uani 1 1 d . . . . .
C10 C 0.60965(8) 1.04747(10) 0.60457(8) 0.01662(18) Uani 1 1 d . . . . .
H10 H 0.574370 1.052340 0.671462 0.020 Uiso 1 1 calc R U . . .
C11 C 0.61697(9) 1.15840(10) 0.53781(9) 0.01966(19) Uani 1 1 d . . . . .
H11 H 0.586538 1.240785 0.560183 0.024 Uiso 1 1 calc R U . . .
C12 C 0.66789(9) 1.15217(10) 0.43862(8) 0.01948(19) Uani 1 1 d . . . . .
H12 H 0.670771 1.229630 0.394664 0.023 Uiso 1 1 calc R U . . .
C13 C 0.71425(8) 1.03347(10) 0.40396(8) 0.01643(18) Uani 1 1 d . . . . .
H13 H 0.748725 1.028844 0.336646 0.020 Uiso 1 1 calc R U . . .
C14 C 0.70903(7) 0.92121(9) 0.47028(7) 0.01298(17) Uani 1 1 d . . . . .
C15 C 0.75258(8) 0.78672(9) 0.46104(7) 0.01238(16) Uani 1 1 d . . . . .
C16 C 0.82103(8) 0.72726(10) 0.38649(7) 0.01558(18) Uani 1 1 d . . . . .
H16 H 0.841991 0.775070 0.324472 0.019 Uiso 1 1 calc R U . . .
C17 C 0.85796(8) 0.59710(10) 0.40448(8) 0.01755(18) Uani 1 1 d . . . . .
H17 H 0.903489 0.554887 0.353803 0.021 Uiso 1 1 calc R U . . .
C18 C 0.82838(8) 0.52768(10) 0.49712(8) 0.01702(18) Uani 1 1 d . . . . .
H18 H 0.855032 0.439003 0.508389 0.020 Uiso 1 1 calc R U . . .
C19 C 0.76092(8) 0.58529(9) 0.57310(7) 0.01461(17) Uani 1 1 d . . . . .
H19 H 0.742183 0.538114 0.636222 0.018 Uiso 1 1 calc R U . . .
C20 C 0.72198(7) 0.71499(9) 0.55280(7) 0.01207(16) Uani 1 1 d . . . . .
C1 C 0.4426(5) 0.2437(5) 0.8096(5) 0.0212(9) Uani 0.9121(8) 1 d . . P A 1
H1A H 0.383731 0.250356 0.862076 0.032 Uiso 0.9121(8) 1 calc R U P A 1
H1B H 0.507705 0.190564 0.841234 0.032 Uiso 0.9121(8) 1 calc R U P A 1
H1C H 0.409103 0.200874 0.742681 0.032 Uiso 0.9121(8) 1 calc R U P A 1
Br1 Br 0.4308(6) 0.2215(6) 0.8129(5) 0.0186(7) Uani 0.0879(8) 1 d . . P A 2


_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 C8 1.2164(11) . ?
N1 C8 1.4027(11) . ?
N1 C9 1.4155(11) . ?
N1 C20 1.4205(11) . ?
C2 C3 1.3977(13) . ?
C2 C7 1.4004(12) . ?
C2 C1 1.531(5) . ?
C2 Br1 1.793(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.3893(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.3975(12) . ?
C5 C6 1.3981(12) . ?
C5 C8 1.4884(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.3911(13) . ?
C7 H7 0.9500 . ?
C9 C10 1.3940(12) . ?
C9 C14 1.4079(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.3914(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.4002(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.3902(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.3965(12) . ?
C14 C15 1.4511(12) . ?
C15 C16 1.3965(12) . ?
C15 C20 1.4090(12) . ?
C16 H16 0.9500 . ?
C16 C17 1.3888(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.4026(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.3939(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.3957(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 123.50(7) . . ?
C8 N1 C20 128.27(8) . . ?
C9 N1 C20 108.07(7) . . ?
C3 C2 C7 118.63(8) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 Br1 120.4(2) . . ?
C7 C2 C1 121.9(3) . . ?
C7 C2 Br1 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.95(8) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.08(8) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.37(8) . . ?
C4 C5 C8 118.26(8) . . ?
C6 C5 C8 122.11(8) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.20(8) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.66(8) . . ?
C6 C7 H7 119.7 . . ?
O1 C8 N1 120.27(8) . . ?
O1 C8 C5 121.45(8) . . ?
N1 C8 C5 118.20(8) . . ?
C10 C9 N1 129.76(8) . . ?
C10 C9 C14 121.65(8) . . ?
C14 C9 N1 108.58(7) . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.17(9) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 121.93(9) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.50(9) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.55(9) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C15 107.33(8) . . ?
C13 C14 C9 120.20(8) . . ?
C13 C14 C15 132.44(8) . . ?
C16 C15 C14 132.15(8) . . ?
C16 C15 C20 120.11(8) . . ?
C20 C15 C14 107.54(7) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.93(8) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.32(8) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.78(9) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.38(8) . . ?
C20 C19 H19 121.3 . . ?
C15 C20 N1 108.29(8) . . ?
C19 C20 N1 130.01(8) . . ?
C19 C20 C15 121.45(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 C9 C10 C11 -178.36(9) . . . . ?
N1 C9 C14 C13 177.90(8) . . . . ?
N1 C9 C14 C15 -3.83(10) . . . . ?
C2 C3 C4 C5 -1.70(14) . . . . ?
C3 C2 C7 C6 3.11(13) . . . . ?
C3 C4 C5 C6 2.84(13) . . . . ?
C3 C4 C5 C8 177.18(8) . . . . ?
C4 C5 C6 C7 -1.01(13) . . . . ?
C4 C5 C8 O1 -38.13(13) . . . . ?
C4 C5 C8 N1 145.06(9) . . . . ?
C5 C6 C7 C2 -1.99(14) . . . . ?
C6 C5 C8 O1 136.04(10) . . . . ?
C6 C5 C8 N1 -40.76(12) . . . . ?
C7 C2 C3 C4 -1.26(14) . . . . ?
C8 N1 C9 C10 -1.07(15) . . . . ?
C8 N1 C9 C14 -179.79(8) . . . . ?
C8 N1 C20 C15 -178.78(8) . . . . ?
C8 N1 C20 C19 -4.59(15) . . . . ?
C8 C5 C6 C7 -175.12(8) . . . . ?
C9 N1 C8 O1 -24.36(14) . . . . ?
C9 N1 C8 C5 152.48(8) . . . . ?
C9 N1 C20 C15 -3.22(10) . . . . ?
C9 N1 C20 C19 170.97(9) . . . . ?
C9 C10 C11 C12 0.55(15) . . . . ?
C9 C14 C15 C16 -172.90(9) . . . . ?
C9 C14 C15 C20 1.83(10) . . . . ?
C10 C9 C14 C13 -0.95(13) . . . . ?
C10 C9 C14 C15 177.32(8) . . . . ?
C10 C11 C12 C13 -0.62(16) . . . . ?
C11 C12 C13 C14 -0.12(14) . . . . ?
C12 C13 C14 C9 0.88(13) . . . . ?
C12 C13 C14 C15 -176.89(9) . . . . ?
C13 C14 C15 C16 5.08(17) . . . . ?
C13 C14 C15 C20 179.81(10) . . . . ?
C14 C9 C10 C11 0.22(14) . . . . ?
C14 C15 C16 C17 174.21(9) . . . . ?
C14 C15 C20 N1 0.86(10) . . . . ?
C14 C15 C20 C19 -173.93(8) . . . . ?
C15 C16 C17 C18 -1.06(14) . . . . ?
C16 C15 C20 N1 176.34(8) . . . . ?
C16 C15 C20 C19 1.56(13) . . . . ?
C16 C17 C18 C19 0.57(15) . . . . ?
C17 C18 C19 C20 0.95(14) . . . . ?
C18 C19 C20 N1 -175.54(9) . . . . ?
C18 C19 C20 C15 -2.00(13) . . . . ?
C20 N1 C8 O1 150.57(9) . . . . ?
C20 N1 C8 C5 -32.59(13) . . . . ?
C20 N1 C9 C10 -176.88(9) . . . . ?
C20 N1 C9 C14 4.40(10) . . . . ?
C20 C15 C16 C17 0.02(13) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C1 C2 C7 C6 -176.7(3) . . . . ?
Br1 C2 C3 C4 -179.7(2) . . . . ?
Br1 C2 C7 C6 -178.5(2) . . . . ?

_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_mw411_a
_database_code_depnum_ccdc_archive 'CCDC 2116288'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-10-17 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19.713 H14.14 Br0.287 N O'
_chemical_formula_sum            'C19.71 H14.14 Br0.29 N O'
_chemical_formula_weight         303.98
_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      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                   11.5964(10)
_cell_length_b                   10.0911(8)
_cell_length_c                   12.3080(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.854(2)
_cell_angle_gamma                90
_cell_volume                     1435.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8336
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0535 before and 0.0340 after correction.
The Ratio of minimum to maximum transmission is 0.8654.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.312
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.537
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3752
_reflns_number_total             4369
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     351
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.024
_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)+(0.0381P)²+0.7795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0931
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C13(H13), C4(H4), C10(H10), C16(H16), C3(H3), C19(H19),
 C11(H11), C12(H12), C18(H18), C17(H17)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.43043(18) 0.77880(18) 0.81342(17) 0.0172(2) Uani 0.2868(11) 1 d . U P
A 2
O1 O 0.60343(8) 0.13920(9) 0.78437(7) 0.0232(2) Uani 1 1 d . U . . .
N1 N 0.65911(8) 0.19885(10) 0.61834(7) 0.01327(18) Uani 1 1 d . U . . .
C5 C 0.57174(9) 0.36375(11) 0.73652(9) 0.0133(2) Uani 1 1 d . U . . .
C9 C 0.72202(9) 0.28451(11) 0.55339(8) 0.0128(2) Uani 1 1 d . U . . .
C15 C 0.70882(9) 0.07902(11) 0.47115(9) 0.0138(2) Uani 1 1 d . U . . .
C7 C 0.46484(9) 0.56051(12) 0.67761(9) 0.0152(2) Uani 1 1 d . U . . .
H7 H 0.420644 0.608420 0.622189 0.018 Uiso 1 1 calc R U . . .
C6 C 0.50991(9) 0.43661(12) 0.65450(8) 0.0141(2) Uani 1 1 d . U . . .
H6 H 0.498542 0.401602 0.582740 0.017 Uiso 1 1 calc R U . . .
C14 C 0.75240(9) 0.21285(11) 0.46161(8) 0.0132(2) Uani 1 1 d . U . . .
C8 C 0.61322(9) 0.22668(12) 0.71777(9) 0.0145(2) Uani 1 1 d . U . . .
C20 C 0.65610(9) 0.07132(11) 0.56984(9) 0.0137(2) Uani 1 1 d . U . . .
C13 C 0.82082(10) 0.27215(12) 0.38707(9) 0.0163(2) Uani 1 1 d . U . . .
H13 H 0.841521 0.224648 0.324982 0.020 Uiso 1 1 calc R U . . .
C4 C 0.58665(9) 0.41503(12) 0.84220(9) 0.0160(2) Uani 1 1 d . U . . .
H4 H 0.625642 0.364252 0.899016 0.019 Uiso 1 1 calc R U . . .
C2 C 0.48453(9) 0.61448(12) 0.78221(9) 0.0153(2) Uani 1 1 d . U . . .
C10 C 0.76114(10) 0.41364(12) 0.57351(9) 0.0154(2) Uani 1 1 d . U . . .
H10 H 0.742449 0.460796 0.636482 0.019 Uiso 1 1 calc R U . . .
C16 C 0.71378(10) -0.03296(12) 0.40499(9) 0.0173(2) Uani 1 1 d . U . . .
H16 H 0.748098 -0.028524 0.337684 0.021 Uiso 1 1 calc R U . . .
C3 C 0.54457(10) 0.54008(12) 0.86429(9) 0.0167(2) Uani 1 1 d . U . . .
H3 H 0.556726 0.575368 0.935899 0.020 Uiso 1 1 calc R U . . .
C19 C 0.60950(10) -0.04645(12) 0.60536(10) 0.0178(2) Uani 1 1 d . U . . .
H19 H 0.574327 -0.051088 0.672215 0.021 Uiso 1 1 calc R U . . .
C11 C 0.82872(10) 0.47076(12) 0.49762(9) 0.0182(2) Uani 1 1 d . U . . .
H11 H 0.855652 0.559017 0.508842 0.022 Uiso 1 1 calc R U . . .
C12 C 0.85799(10) 0.40146(13) 0.40522(9) 0.0187(2) Uani 1 1 d . U . . .
H12 H 0.903634 0.443378 0.354632 0.022 Uiso 1 1 calc R U . . .
C18 C 0.61656(10) -0.15707(12) 0.53890(11) 0.0203(2) Uani 1 1 d . U . . .
H18 H 0.586040 -0.239050 0.561346 0.024 Uiso 1 1 calc R U . . .
C17 C 0.66739(10) -0.15097(13) 0.43983(10) 0.0205(2) Uani 1 1 d . U . . .
H17 H 0.670199 -0.228220 0.396018 0.025 Uiso 1 1 calc R U . . .
C1 C 0.4427(8) 0.7556(7) 0.8084(7) 0.0215(13) Uani 0.7132(11) 1 d . U P A 1
H1A H 0.409394 0.797849 0.741234 0.032 Uiso 0.7132(11) 1 calc R U P A 1
H1B H 0.508402 0.808159 0.839654 0.032 Uiso 0.7132(11) 1 calc R U P A 1
H1C H 0.383861 0.750079 0.860844 0.032 Uiso 0.7132(11) 1 calc R U P A 1


_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 C2 1.825(2) . ?
O1 C8 1.2165(14) . ?
N1 C9 1.4203(13) . ?
N1 C8 1.4035(13) . ?
N1 C20 1.4179(14) . ?
C5 C6 1.3969(15) . ?
C5 C8 1.4889(16) . ?
C5 C4 1.3969(15) . ?
C9 C14 1.4108(14) . ?
C9 C10 1.3950(16) . ?
C15 C14 1.4502(16) . ?
C15 C20 1.4075(15) . ?
C15 C16 1.3968(16) . ?
C7 H7 0.9500 . ?
C7 C6 1.3937(16) . ?
C7 C2 1.3988(15) . ?
C6 H6 0.9500 . ?
C14 C13 1.3973(15) . ?
C20 C19 1.3912(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.3864(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3882(17) . ?
C2 C3 1.3964(16) . ?
C2 C1 1.547(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.3939(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3893(17) . ?
C3 H3 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.3903(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.4010(16) . ?
C12 H12 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.4000(17) . ?
C17 H17 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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 N1 C9 128.30(10) . . ?
C8 N1 C20 123.44(9) . . ?
C20 N1 C9 108.11(8) . . ?
C6 C5 C8 121.99(10) . . ?
C6 C5 C4 119.57(10) . . ?
C4 C5 C8 118.18(10) . . ?
C14 C9 N1 108.28(9) . . ?
C10 C9 N1 130.04(10) . . ?
C10 C9 C14 121.43(10) . . ?
C20 C15 C14 107.53(10) . . ?
C16 C15 C14 132.40(10) . . ?
C16 C15 C20 120.05(10) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C2 120.15(10) . . ?
C2 C7 H7 119.9 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.21(10) . . ?
C7 C6 H6 119.9 . . ?
C9 C14 C15 107.47(9) . . ?
C13 C14 C9 120.02(10) . . ?
C13 C14 C15 132.31(10) . . ?
O1 C8 N1 120.42(11) . . ?
O1 C8 C5 121.33(10) . . ?
N1 C8 C5 118.18(9) . . ?
C15 C20 N1 108.43(9) . . ?
C19 C20 N1 129.75(10) . . ?
C19 C20 C15 121.80(11) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 C14 118.91(10) . . ?
C12 C13 H13 120.5 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.08(10) . . ?
C3 C4 H4 120.0 . . ?
C7 C2 Br1 121.01(11) . . ?
C7 C2 C1 121.4(4) . . ?
C3 C2 Br1 119.69(11) . . ?
C3 C2 C7 119.28(11) . . ?
C3 C2 C1 119.3(4) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 C9 117.39(10) . . ?
C11 C10 H10 121.3 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.52(11) . . ?
C17 C16 H16 120.7 . . ?
C4 C3 C2 120.60(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C20 C19 H19 121.4 . . ?
C18 C19 C20 117.21(11) . . ?
C18 C19 H19 121.4 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.74(11) . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 120.48(10) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C19 C18 H18 119.1 . . ?
C19 C18 C17 121.82(11) . . ?
C17 C18 H18 119.1 . . ?
C16 C17 C18 120.60(11) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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 C2 C3 C4 -179.86(11) . . . . ?
N1 C9 C14 C15 -0.97(12) . . . . ?
N1 C9 C14 C13 -176.39(10) . . . . ?
N1 C9 C10 C11 175.45(11) . . . . ?
N1 C20 C19 C18 178.37(11) . . . . ?
C5 C4 C3 C2 1.62(17) . . . . ?
C9 N1 C8 O1 -150.46(12) . . . . ?
C9 N1 C8 C5 32.59(16) . . . . ?
C9 N1 C20 C15 -4.36(12) . . . . ?
C9 N1 C20 C19 176.84(11) . . . . ?
C9 C14 C13 C12 0.13(16) . . . . ?
C9 C10 C11 C12 -0.82(17) . . . . ?
C15 C14 C13 C12 -173.95(11) . . . . ?
C15 C20 C19 C18 -0.28(17) . . . . ?
C15 C16 C17 C18 0.20(18) . . . . ?
C7 C2 C3 C4 1.40(16) . . . . ?
C6 C5 C8 O1 -136.10(12) . . . . ?
C6 C5 C8 N1 40.82(15) . . . . ?
C6 C5 C4 C3 -2.79(16) . . . . ?
C6 C7 C2 Br1 178.01(11) . . . . ?
C6 C7 C2 C3 -3.26(16) . . . . ?
C6 C7 C2 C1 175.9(4) . . . . ?
C14 C9 C10 C11 1.86(16) . . . . ?
C14 C15 C20 N1 3.73(12) . . . . ?
C14 C15 C20 C19 -177.36(10) . . . . ?
C14 C15 C16 C17 176.96(11) . . . . ?
C14 C13 C12 C11 0.89(17) . . . . ?
C8 N1 C9 C14 178.95(10) . . . . ?
C8 N1 C9 C10 4.71(19) . . . . ?
C8 N1 C20 C15 179.70(9) . . . . ?
C8 N1 C20 C19 0.91(18) . . . . ?
C8 C5 C6 C7 175.00(10) . . . . ?
C8 C5 C4 C3 -177.08(10) . . . . ?
C20 N1 C9 C14 3.28(12) . . . . ?
C20 N1 C9 C10 -170.97(11) . . . . ?
C20 N1 C8 O1 24.61(16) . . . . ?
C20 N1 C8 C5 -152.34(10) . . . . ?
C20 C15 C14 C9 -1.70(12) . . . . ?
C20 C15 C14 C13 172.93(12) . . . . ?
C20 C15 C16 C17 -0.98(16) . . . . ?
C20 C19 C18 C17 -0.52(18) . . . . ?
C4 C5 C6 C7 0.93(16) . . . . ?
C4 C5 C8 O1 38.05(16) . . . . ?
C4 C5 C8 N1 -145.03(10) . . . . ?
C2 C7 C6 C5 2.10(16) . . . . ?
C10 C9 C14 C15 173.87(10) . . . . ?
C10 C9 C14 C13 -1.55(16) . . . . ?
C10 C11 C12 C13 -0.55(18) . . . . ?
C16 C15 C14 C9 -179.83(12) . . . . ?
C16 C15 C14 C13 -5.2(2) . . . . ?
C16 C15 C20 N1 -177.87(10) . . . . ?
C16 C15 C20 C19 1.04(16) . . . . ?
C19 C18 C17 C16 0.57(19) . . . . ?
C1 C2 C3 C4 -177.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
