# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2279
_audit_creation_date             2014-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
"2-(5-hydroxy-4-methyl-2-(4-methyl-3-nitropyrrolidin-2-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)ethyl 2-methylbenzoate"
_chemical_formula_moiety         'C27 H27 Br N2 O5'
_chemical_formula_sum            'C27 H27 Br N2 O5'
_chemical_formula_weight         539.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H27 N2 O5 Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.89050(7)
_cell_length_b                   23.7962(3)
_cell_length_c                   9.09712(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.9605(13)
_cell_angle_gamma                90
_cell_volume                     1242.67(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23509
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      32.7650
_cell_measurement_theta_min      2.8720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Clear yellowish'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.3046
_exptl_crystal_size_mid          0.1741
_exptl_crystal_size_min          0.1026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40829
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.960
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00  107.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695    0.0000 -120.0000 177

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   95.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695   77.0000   30.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   95.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695   77.0000  -90.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega  -56.00   43.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695  -38.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  5 omega  -80.00   -7.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.8195  133.0000   74.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00  106.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695 -178.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
  7 omega    7.00   79.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695 -133.0000    6.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega  -10.00   92.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       18.5695   57.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
  9 omega  -44.00   54.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.8195   38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
 10 omega -107.00  -34.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      -19.8195  178.0000  150.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0047798000
_diffrn_orient_matrix_UB_12      0.0226077000
_diffrn_orient_matrix_UB_13      0.0514085000
_diffrn_orient_matrix_UB_21      -0.0084711000
_diffrn_orient_matrix_UB_22      0.0194239000
_diffrn_orient_matrix_UB_23      -0.0601266000
_diffrn_orient_matrix_UB_31      -0.1231925000
_diffrn_orient_matrix_UB_32      -0.0004571000
_diffrn_orient_matrix_UB_33      -0.0118647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                8404
_reflns_number_total             8771
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.236
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 
;
 Flack x determined using 3849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         8771
_refine_ls_number_restraints     268
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.028
_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)+(0.0800P)²+1.8490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(O1H) = Uiso(O1I)
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(O1I)=1-FVAR(1)
 Sof(O1H)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C11(H11), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C19(H19A,H19B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15), C17(H17), N22(H22), C1E(H1E), C1G(H1G), C1K(H1K), C1M(H1M),
 C1Y(H1Y), C2(H2), C1(H1)
5.d Idealised Me refined as rotating group:
 C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,H1DC)
5.e Idealised tetrahedral OH refined as rotating group:
 O1P(H1P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.72539(6) 0.40669(2) -0.04593(4) 0.02322(11) Uani 1 1 d . . . . .
O1 O 0.8342(5) 0.26922(13) 0.0468(3) 0.0183(5) Uani 1 1 d . . . . .
O2 O 0.3263(5) 0.38375(12) 0.1049(3) 0.0151(5) Uani 1 1 d . . . . .
C3 C 0.3019(7) 0.43834(15) 0.1321(5) 0.0159(6) Uani 1 1 d . . . . .
C5 C 0.2325(6) 0.17694(14) 0.1667(3) 0.0103(5) Uani 1 1 d . . . . .
H5 H 0.0962 0.1575 0.1687 0.012 Uiso 1 1 calc R . . . .
C4 C 0.7306(6) 0.26319(13) 0.3553(4) 0.0100(5) Uani 1 1 d . . . . .
H4 H 0.8812 0.2596 0.3273 0.012 Uiso 1 1 calc R . . . .
C7 C 0.3333(6) 0.18154(15) 0.0522(4) 0.0132(5) Uani 1 1 d . . . . .
C8 C 0.5567(6) 0.23058(13) 0.2429(4) 0.0097(5) Uani 1 1 d . . . . .
C6 C 0.9678(6) 0.27017(15) 0.6177(4) 0.0147(6) Uani 1 1 d . . . . .
H6A H 0.9631 0.2636 0.7222 0.018 Uiso 1 1 calc R . . . .
H6B H 1.1108 0.2537 0.6015 0.018 Uiso 1 1 calc R . . . .
C9 C 0.4143(6) 0.33962(15) 0.3595(4) 0.0137(6) Uani 1 1 d . . . . .
H9A H 0.3598 0.3101 0.4165 0.016 Uiso 1 1 calc R . . . .
H9B H 0.4110 0.3746 0.4138 0.016 Uiso 1 1 calc R . . . .
C10 C 0.7985(6) 0.17619(15) 0.5285(4) 0.0119(5) Uani 1 1 d . . . . .
C11 C 0.6703(6) 0.32679(13) 0.3524(4) 0.0110(5) Uani 1 1 d . . . . .
H11 H 0.6916 0.3415 0.2557 0.013 Uiso 1 1 calc R . . . .
C12 C 0.7601(6) 0.23926(14) 0.5164(4) 0.0107(5) Uani 1 1 d . . . . .
H12 H 0.6194 0.2482 0.5524 0.013 Uiso 1 1 calc R . . . .
C14 C 0.5368(6) 0.21590(13) 0.0948(4) 0.0110(5) Uani 1 1 d . . . . .
C13 C 0.9767(7) 0.33250(15) 0.5928(4) 0.0153(6) Uani 1 1 d . . . . .
C15 C 0.6552(6) 0.14231(15) 0.5939(4) 0.0136(6) Uani 1 1 d . . . . .
H15 H 0.5255 0.1579 0.6207 0.016 Uiso 1 1 calc R . . . .
C17 C 0.9879(7) 0.15157(16) 0.4835(4) 0.0156(6) Uani 1 1 d . . . . .
H17 H 1.0822 0.1734 0.4367 0.019 Uiso 1 1 calc R . . . .
C18 C 0.8402(6) 0.35851(15) 0.4754(4) 0.0137(6) Uani 1 1 d . . . . .
C19 C 0.2473(7) 0.34437(15) 0.2068(4) 0.0145(6) Uani 1 1 d . . . . .
H19A H 0.2274 0.3075 0.1600 0.017 Uiso 1 1 calc R . . . .
H19B H 0.0966 0.3565 0.2211 0.017 Uiso 1 1 calc R . . . .
O1A O 0.2323(7) 0.45596(13) 0.2388(4) 0.0248(7) Uani 1 1 d . . . . .
N22 N 0.3748(5) 0.20783(11) 0.2871(3) 0.0076(4) Uani 1 1 d . . . . .
H22 H 0.3478 0.2114 0.3757 0.009 Uiso 1 1 calc R . . . .
C1B C 0.5220(7) 0.46931(17) -0.0711(4) 0.0177(6) Uani 1 1 d . . . . .
C1C C 0.8410(8) 0.42114(15) 0.4499(5) 0.0210(7) Uani 1 1 d . . . . .
H1CA H 0.9037 0.4290 0.3634 0.031 Uiso 1 1 calc GR . . . .
H1CB H 0.9353 0.4391 0.5371 0.031 Uiso 1 1 calc GR . . . .
H1CC H 0.6846 0.4352 0.4331 0.031 Uiso 1 1 calc GR . . . .
C1D C 0.2331(7) 0.15198(17) -0.0928(4) 0.0201(7) Uani 1 1 d . . . . .
H1DA H 0.3265 0.1197 -0.1020 0.030 Uiso 1 1 calc GR . . . .
H1DB H 0.2315 0.1770 -0.1757 0.030 Uiso 1 1 calc GR . . . .
H1DC H 0.0768 0.1402 -0.0938 0.030 Uiso 1 1 calc GR . . . .
C1E C 0.7040(7) 0.08522(15) 0.6196(4) 0.0170(6) Uani 1 1 d . . . . .
H1E H 0.6084 0.0633 0.6651 0.020 Uiso 1 1 calc R . . . .
C1F C 0.3535(7) 0.47699(15) 0.0139(4) 0.0163(6) Uani 1 1 d . . . . .
C1G C 0.2100(8) 0.5279(2) -0.0144(5) 0.0276(9) Uani 1 1 d . . . . .
H1G H 0.0991 0.5349 0.0417 0.033 Uiso 1 1 calc R . . . .
O1H O 0.6285(15) 0.2203(4) -0.1369(9) 0.0217(8) Uiso 0.443(10) 1 d . . P A 1
N1I N 0.6869(6) 0.23317(16) 0.0002(4) 0.0197(6) Uani 1 1 d . . . . .
C1K C 0.2388(8) 0.56497(18) -0.1222(5) 0.0247(8) Uani 1 1 d . . . . .
H1K H 0.1437 0.5965 -0.1414 0.030 Uiso 1 1 calc R . . . .
C1M C 1.0360(7) 0.09431(17) 0.5086(5) 0.0196(7) Uani 1 1 d . . . . .
H1M H 1.1629 0.0783 0.4791 0.024 Uiso 1 1 calc R . . . .
O1P O 1.1618(9) 0.3611(2) 0.7113(5) 0.0432(10) Uani 1 1 d . . . . .
H1P H 1.2904 0.3488 0.7074 0.065 Uiso 1 1 calc GR . . . .
C1Y C 0.8946(8) 0.06107(16) 0.5777(5) 0.0203(7) Uani 1 1 d . . . . .
H1Y H 0.9278 0.0231 0.5954 0.024 Uiso 1 1 calc R . . . .
C2 C 0.4094(9) 0.55633(19) -0.2048(5) 0.0249(8) Uani 1 1 d . . . . .
H2 H 0.4278 0.5823 -0.2775 0.030 Uiso 1 1 calc R . . . .
C1 C 0.5503(8) 0.5096(2) -0.1791(5) 0.0230(8) Uani 1 1 d . . . . .
H1 H 0.6651 0.5046 -0.2334 0.028 Uiso 1 1 calc R . . . .
O1I O 0.6870(12) 0.2035(3) -0.1124(7) 0.0217(8) Uiso 0.557(10) 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
Br1 C1B 1.894(4) . ?
O1 N1I 1.226(4) . ?
O2 C3 1.336(4) . ?
O2 C19 1.465(5) . ?
C3 O1A 1.210(5) . ?
C3 C1F 1.497(5) . ?
C5 C7 1.314(5) . ?
C5 N22 1.426(4) . ?
C4 C8 1.492(4) . ?
C4 C11 1.553(5) . ?
C4 C12 1.545(5) . ?
C7 C14 1.431(5) . ?
C7 C1D 1.495(5) . ?
C8 C14 1.371(4) . ?
C8 N22 1.340(4) . ?
C6 C12 1.543(5) . ?
C6 C13 1.503(5) . ?
C9 C11 1.554(5) . ?
C9 C19 1.516(5) . ?
C10 C12 1.518(5) . ?
C10 C15 1.393(5) . ?
C10 C17 1.400(5) . ?
C11 C18 1.523(5) . ?
C14 N1I 1.426(5) . ?
C13 C18 1.336(5) . ?
C13 O1P 1.512(5) . ?
C15 C1E 1.397(5) . ?
C17 C1M 1.400(6) . ?
C18 C1C 1.508(5) . ?
C1B C1F 1.400(6) . ?
C1B C1 1.409(6) . ?
C1E C1Y 1.389(6) . ?
C1F C1G 1.467(7) . ?
C1G C1K 1.357(6) . ?
O1H N1I 1.254(8) . ?
N1I O1I 1.244(7) . ?
C1K C2 1.398(7) . ?
C1M C1Y 1.396(6) . ?
C2 C1 1.376(7) . ?

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
C3 O2 C19 116.2(3) . . ?
O2 C3 C1F 114.6(3) . . ?
O1A C3 O2 123.7(4) . . ?
O1A C3 C1F 121.5(3) . . ?
C7 C5 N22 105.9(3) . . ?
C8 C4 C11 112.1(3) . . ?
C8 C4 C12 111.8(3) . . ?
C12 C4 C11 110.6(3) . . ?
C5 C7 C14 109.4(3) . . ?
C5 C7 C1D 120.1(3) . . ?
C14 C7 C1D 130.5(3) . . ?
C14 C8 C4 134.4(3) . . ?
N22 C8 C4 118.5(3) . . ?
N22 C8 C14 107.1(3) . . ?
C13 C6 C12 115.5(3) . . ?
C19 C9 C11 114.4(3) . . ?
C15 C10 C12 120.6(3) . . ?
C15 C10 C17 118.8(3) . . ?
C17 C10 C12 120.5(3) . . ?
C4 C11 C9 114.3(3) . . ?
C18 C11 C4 111.1(3) . . ?
C18 C11 C9 110.8(3) . . ?
C6 C12 C4 107.2(3) . . ?
C10 C12 C4 114.6(3) . . ?
C10 C12 C6 110.0(3) . . ?
C8 C14 C7 107.1(3) . . ?
C8 C14 N1I 126.3(3) . . ?
N1I C14 C7 126.6(3) . . ?
C6 C13 O1P 112.4(3) . . ?
C18 C13 C6 122.8(3) . . ?
C18 C13 O1P 124.8(4) . . ?
C10 C15 C1E 120.8(3) . . ?
C10 C17 C1M 120.4(4) . . ?
C13 C18 C11 122.4(3) . . ?
C13 C18 C1C 123.9(3) . . ?
C1C C18 C11 113.6(3) . . ?
O2 C19 C9 113.2(3) . . ?
C8 N22 C5 110.5(3) . . ?
C1F C1B Br1 122.9(3) . . ?
C1F C1B C1 120.4(4) . . ?
C1 C1B Br1 116.7(3) . . ?
C1Y C1E C15 120.3(3) . . ?
C1B C1F C3 126.8(3) . . ?
C1B C1F C1G 117.6(3) . . ?
C1G C1F C3 115.6(3) . . ?
C1K C1G C1F 120.2(4) . . ?
O1 N1I C14 118.6(3) . . ?
O1 N1I O1H 121.9(5) . . ?
O1 N1I O1I 123.5(4) . . ?
O1H N1I C14 117.5(4) . . ?
O1I N1I C14 116.6(4) . . ?
C1G C1K C2 120.9(4) . . ?
C1Y C1M C17 120.3(4) . . ?
C1E C1Y C1M 119.3(3) . . ?
C1 C2 C1K 120.4(4) . . ?
C2 C1 C1B 120.5(4) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 3 5 0.0264 0.0001 2.9806 4.9483 0.3218 -0.2396 -0.0601
5 2 -1 0.1367 4.9500 1.9941 -0.9901 0.0178 0.0563 -0.5990
0 -1 0 0.0951 -0.0000 -0.9899 0.0006 -0.0224 -0.0193 0.0004
0 1 0 0.0623 0.0004 0.9998 -0.0001 0.0226 0.0194 -0.0005
0 1 -5 0.0496 -0.0000 0.9748 -4.9505 -0.2325 0.3166 0.0583
-5 1 1 0.1414 -4.9498 0.9733 0.9883 0.0492 0.0014 0.5976

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Air-sensitive
_database_code_depnum_ccdc_archive 'CCDC 1026165'
