# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dwb1344
_database_code_depnum_ccdc_archive 'CCDC 2123966'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C17 H22 N O'
_chemical_formula_sum            'C17 H22 Br N O'
_chemical_formula_weight         336.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H22 N1 O1 Br'
_chemical_oxdiff_usercomment     'Linda LJM385'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7843(3)
_cell_length_b                   8.3585(3)
_cell_length_c                   15.1607(7)
_cell_angle_alpha                97.295(3)
_cell_angle_beta                 93.314(4)
_cell_angle_gamma                111.978(4)
_cell_volume                     785.58(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3252
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.7710
_cell_measurement_theta_min      3.2600
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.486
_exptl_absorpt_coefficient_mu    2.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug 2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.3226
_exptl_crystal_size_mid          0.1893
_exptl_crystal_size_min          0.0387
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6843
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.081
_diffrn_reflns_theta_min         3.180
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -89.00  -12.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -57.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00   12.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -19.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega  -78.00  -37.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  125.0000  -49.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   38.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    6.00   84.00   1.0000   32.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735 -125.0000 -127.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0916442000
_diffrn_orient_matrix_UB_12      -0.0215041000
_diffrn_orient_matrix_UB_13      -0.0009547000
_diffrn_orient_matrix_UB_21      0.0198410000
_diffrn_orient_matrix_UB_22      0.0212889000
_diffrn_orient_matrix_UB_23      0.0473279000
_diffrn_orient_matrix_UB_31      -0.0639357000
_diffrn_orient_matrix_UB_32      -0.0876351000
_diffrn_orient_matrix_UB_33      0.0036681000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3915
_reflns_number_total             4465
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug 2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug 2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug 2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.797
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.076
_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)+(0.0390P)²+0.3315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.63646(3) 0.75245(3) 0.07374(2) 0.01915(7) Uani 1 1 d . . . . .
C1 C -0.0307(4) 0.5445(3) 0.12055(16) 0.0237(5) Uani 1 1 d . . . . .
H1 H -0.031616 0.658741 0.130090 0.028 Uiso 1 1 calc R U . . .
C2 C 0.1392(4) 0.5143(3) 0.15737(16) 0.0210(4) Uani 1 1 d . . . . .
H2 H 0.256737 0.608972 0.191241 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1422(3) 0.3464(3) 0.14584(14) 0.0157(4) Uani 1 1 d . . . . .
C4 C -0.0336(4) 0.2139(3) 0.09292(15) 0.0216(4) Uani 1 1 d . . . . .
H4 H -0.038052 0.098014 0.082219 0.026 Uiso 1 1 calc R U . . .
C5 C -0.1991(4) 0.2499(3) 0.05648(16) 0.0233(5) Uani 1 1 d . . . . .
H5 H -0.316932 0.158940 0.020651 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3182(3) 0.3099(3) 0.18813(14) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.4766(4) 0.4371(3) 0.25127(16) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.472465 0.549785 0.265260 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6374(4) 0.4023(3) 0.29322(16) 0.0220(5) Uani 1 1 d . . . . .
H8 H 0.741604 0.490564 0.336165 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6494(3) 0.2387(3) 0.27352(14) 0.0173(4) Uani 1 1 d . . . . .
C10 C 0.4946(4) 0.1097(3) 0.21080(14) 0.0191(4) Uani 1 1 d . . . . .
H10 H 0.500085 -0.002538 0.196716 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3327(4) 0.1466(3) 0.16922(14) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.228178 0.058142 0.126468 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8255(4) 0.0504(3) 0.30693(15) 0.0209(4) Uani 1 1 d . . . . .
H12A H 0.832686 0.011580 0.243155 0.025 Uiso 1 1 calc R U . . .
H12B H 0.695330 -0.034929 0.325805 0.025 Uiso 1 1 calc R U . . .
C13 C 1.0216(4) 0.0599(3) 0.36326(15) 0.0193(4) Uani 1 1 d . . . . .
H13A H 1.025720 0.116763 0.425134 0.023 Uiso 1 1 calc R U . . .
H13B H 1.151981 0.130943 0.338347 0.023 Uiso 1 1 calc R U . . .
C14 C 1.0160(4) -0.1241(3) 0.36423(15) 0.0215(4) Uani 1 1 d . . . . .
H14A H 0.889699 -0.190766 0.392854 0.026 Uiso 1 1 calc R U . . .
H14B H 0.997064 -0.183106 0.301627 0.026 Uiso 1 1 calc R U . . .
C15 C 1.2146(4) -0.1313(3) 0.41296(16) 0.0218(4) Uani 1 1 d . . . . .
H15A H 1.244604 -0.060774 0.473405 0.026 Uiso 1 1 calc R U . . .
H15B H 1.338746 -0.078909 0.379928 0.026 Uiso 1 1 calc R U . . .
C16 C 1.1885(4) -0.3181(3) 0.42175(17) 0.0249(5) Uani 1 1 d . . . . .
H16A H 1.066315 -0.368803 0.456061 0.030 Uiso 1 1 calc R U . . .
H16B H 1.153410 -0.388996 0.361249 0.030 Uiso 1 1 calc R U . . .
C17 C 1.3855(4) -0.3314(4) 0.46761(18) 0.0309(5) Uani 1 1 d . . . . .
H17A H 1.508056 -0.279965 0.434661 0.046 Uiso 1 1 calc R U . . .
H17B H 1.359682 -0.454530 0.468726 0.046 Uiso 1 1 calc R U . . .
H17C H 1.415999 -0.268172 0.529049 0.046 Uiso 1 1 calc R U . . .
N1 N -0.1958(3) 0.4124(3) 0.07101(13) 0.0213(4) Uani 1 1 d . . . . .
H1A H -0.304(4) 0.433(3) 0.0480(17) 0.020(7) Uiso 1 1 d . . . . .
O1 O 0.8167(3) 0.2203(2) 0.31820(11) 0.0218(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.372(3) . ?
C1 N1 1.343(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(3) . ?
C3 C4 1.403(3) . ?
C3 C6 1.471(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(3) . ?
C5 H5 0.9500 . ?
C5 N1 1.340(3) . ?
C6 C7 1.403(3) . ?
C6 C11 1.400(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(3) . ?
C9 C10 1.395(3) . ?
C9 O1 1.356(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.509(3) . ?
C12 O1 1.433(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.518(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1A 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
N1 C1 C2 120.0(2) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 116.4(2) . . ?
C2 C3 C6 121.92(19) . . ?
C4 C3 C6 121.7(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C5 C4 120.5(2) . . ?
N1 C5 H5 119.7 . . ?
C7 C6 C3 121.05(19) . . ?
C11 C6 C3 121.89(19) . . ?
C11 C6 C7 117.0(2) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.2(2) . . ?
O1 C9 C8 115.51(19) . . ?
O1 C9 C10 125.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C6 C11 H11 118.9 . . ?
C10 C11 C6 122.2(2) . . ?
C10 C11 H11 118.9 . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
O1 C12 H12A 110.0 . . ?
O1 C12 H12B 110.0 . . ?
O1 C12 C13 108.65(18) . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C12 C13 C14 109.63(18) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.70(19) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.24(19) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.9(2) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N1 H1A 119.3(18) . . ?
C5 N1 C1 121.3(2) . . ?
C5 N1 H1A 119.4(18) . . ?
C9 O1 C12 117.77(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Br1 0.88(3) 2.66(3) 3.323(2) 133(2) 2_565 yes

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
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C2 C3 C6 -177.2(2) . . . . ?
C2 C1 N1 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C6 C7 8.4(3) . . . . ?
C2 C3 C6 C11 -173.2(2) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C6 C7 C8 177.8(2) . . . . ?
C3 C6 C11 C10 -178.1(2) . . . . ?
C4 C3 C6 C7 -170.5(2) . . . . ?
C4 C3 C6 C11 7.9(3) . . . . ?
C4 C5 N1 C1 0.7(3) . . . . ?
C6 C3 C4 C5 177.9(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C6 C11 C10 0.4(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 O1 179.1(2) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C8 C9 O1 C12 174.2(2) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C10 C9 O1 C12 -6.2(3) . . . . ?
C11 C6 C7 C8 -0.6(3) . . . . ?
C12 C13 C14 C15 175.37(19) . . . . ?
C13 C12 O1 C9 -179.25(18) . . . . ?
C13 C14 C15 C16 172.9(2) . . . . ?
C14 C15 C16 C17 178.3(2) . . . . ?
N1 C1 C2 C3 -1.4(3) . . . . ?
O1 C9 C10 C11 -179.3(2) . . . . ?
O1 C12 C13 C14 171.06(18) . . . . ?

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 0 1 0.0194 0.0000 -0.0000 1.0000 -0.0010 0.0473 0.0037
0 0 -1 0.0194 -0.0000 0.0000 -1.0000 0.0010 -0.0473 -0.0037
0 -1 0 0.1002 0.0000 -1.0000 -0.0000 0.0215 -0.0213 0.0876
0 1 0 0.1022 -0.0000 1.0000 0.0000 -0.0215 0.0213 -0.0876
1 -1 0 0.0941 1.0000 -1.0000 0.0000 0.1131 -0.0014 0.0237
-1 1 0 0.0951 -1.0000 1.0000 -0.0000 -0.1131 0.0014 -0.0237

_olex2_date_sample_data_collection 1380028752.0
_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_dwb1368
_database_code_depnum_ccdc_archive 'CCDC 2123968'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 I2 N O'
_chemical_formula_sum            'C15 H17 I2 N O'
_chemical_formula_weight         481.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H17 O1 N1 I2'
_chemical_oxdiff_usercomment     'Linda E380F'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7375(3)
_cell_length_b                   9.2799(4)
_cell_length_c                   10.6024(7)
_cell_angle_alpha                106.226(5)
_cell_angle_beta                 98.182(4)
_cell_angle_gamma                100.729(4)
_cell_volume                     793.61(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.7300
_cell_measurement_theta_min      3.4670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.955
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2291
_exptl_crystal_size_mid          0.1083
_exptl_crystal_size_min          0.0148
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9193
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         28.112
_diffrn_reflns_theta_min         2.950
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784    0.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega   -9.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  8 omega  -56.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -37.0000    0.0000 98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0137097000
_diffrn_orient_matrix_UB_12      0.0245097000
_diffrn_orient_matrix_UB_13      0.0661667000
_diffrn_orient_matrix_UB_21      0.0790880000
_diffrn_orient_matrix_UB_22      -0.0008546000
_diffrn_orient_matrix_UB_23      0.0261279000
_diffrn_orient_matrix_UB_31      0.0261966000
_diffrn_orient_matrix_UB_32      0.0781985000
_diffrn_orient_matrix_UB_33      0.0030207000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71071
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2759
_reflns_number_total             3348
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0130P)²+0.3111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0489
_refine_special_details          
;
 The whole molecule shows disorder due to a 180 degrees rotation. This has
 been modelled in two positions with a refined occupancy ratio of
 0.9774:0.0226(7). Due to proximity the ADPs of close atoms in the major
 and minor part have been constrained to be the same (e.g. C9 and N1A).
 Due to the low proportion of the minor part the benzene and pyridine rings
 were constrained to be regular hexagons. The OC4H9 side chain was
 constrained to be in the same plane as the benzene ring and bond distances
 and angles between atoms in the OC4H9 side chain were restrained to values
 similar to the corresponding distances in the major component. Distances
 between the two iodine atoms, the iodine and nitrogen atoms and the
 carbon atoms joining the two rings (C3A and C6A) in the minor component were also
 restrained to values close to those in the major component.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14A-C15A
 1.55 with sigma of 0.02
 C12A-C13A = C13A-C14A
 1.51 with sigma of 0.02
 O1A-C12A
 1.41 with sigma of 0.02
 C9A-O1A
 1.36 with sigma of 0.02
 I1A-I2A
 2.8 with sigma of 0.02
 C3A-C6A
 1.45 with sigma of 0.02
 I1A-N1A
 2.45 with sigma of 0.02
 C13A-C15A
 2.54 with sigma of 0.04
 C12A-C14A
 2.52 with sigma of 0.04
 O1A-C13A
 2.37 with sigma of 0.04
 C9A-C12A
 2.38 with sigma of 0.04
3. Restrained planarity
 C6A, C7A, C8A, C9A, C10A, C11A, O1A, C12A, C13A, C14A, C15A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(I2) = Uanis(C15A)
Uanis(I1) = Uanis(C12A) = Uanis(C13A) = Uanis(C14A)
Uanis(C3) = Uanis(C6A)
Uanis(C2) = Uanis(C11A)
Uanis(C4) = Uanis(C7A)
Uanis(C5) = Uanis(C8A)
Uanis(C1) = Uanis(C10A)
Uanis(N1) = Uanis(C9A) = Uanis(O1A)
Uanis(C15) = Uanis(I2A)
Uanis(C13) = Uanis(I1A)
Uanis(C9) = Uanis(N1A)
Uanis(C8) = Uanis(C5A)
Uanis(C7) = Uanis(C4A)
Uanis(C10) = Uanis(C1A)
Uanis(C11) = Uanis(C2A)
Uanis(C6) = Uanis(C3A)
5. Others
 Sof(C6A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(C8A)=Sof(H8A)=
 Sof(C7A)=Sof(H7A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(I1A)=
 Sof(I2A)=Sof(N1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(O1A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(I1)=Sof(I2)=
 Sof(N1)=Sof(O1)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C12A(H12C,H12D), C13A(H13C,
 H13D), C14A(H14C,H14D)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11),
 C11A(H11A), C10A(H10A), C8A(H8A), C7A(H7A), C1A(H1A), C2A(H2A), C4A(H4A),
 C5A(H5A)
6.c Fitted hexagon refined as free rotating group:
 C6A(C11A,C10A,C9A,C8A,C7A), N1A(C1A,C2A,C3A,C4A,C5A)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C15A(H15D,H15E,H15F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.7145(4) 0.5470(4) 0.8351(4) 0.0235(8) Uani 0.9771(7) 1 d . . P A 1
H1 H 0.743564 0.505224 0.904669 0.028 Uiso 0.9771(7) 1 calc R U P A 1
C2 C 0.7587(4) 0.4940(4) 0.7140(4) 0.0233(8) Uani 0.9771(7) 1 d . . P A 1
H2 H 0.817097 0.416185 0.701082 0.028 Uiso 0.9771(7) 1 calc R U P A 1
C3 C 0.7181(4) 0.5539(4) 0.6102(4) 0.0205(8) Uani 0.9771(7) 1 d . . P A 1
C4 C 0.6298(4) 0.6666(4) 0.6373(4) 0.0251(8) Uani 0.9771(7) 1 d . . P A 1
H4 H 0.597083 0.709743 0.569555 0.030 Uiso 0.9771(7) 1 calc R U P A 1
C5 C 0.5900(4) 0.7152(4) 0.7600(4) 0.0246(8) Uani 0.9771(7) 1 d . . P A 1
H5 H 0.531386 0.792692 0.776455 0.030 Uiso 0.9771(7) 1 calc R U P A 1
C6 C 0.7629(4) 0.5032(4) 0.4804(4) 0.0207(8) Uani 0.9771(7) 1 d . . P A 1
C7 C 0.7956(4) 0.3593(4) 0.4292(4) 0.0233(8) Uani 0.9771(7) 1 d . . P A 1
H7 H 0.794366 0.292591 0.482820 0.028 Uiso 0.9771(7) 1 calc R U P A 1
C8 C 0.8300(4) 0.3100(4) 0.3025(4) 0.0245(8) Uani 0.9771(7) 1 d . . P A 1
H8 H 0.851141 0.210865 0.270051 0.029 Uiso 0.9771(7) 1 calc R U P A 1
C9 C 0.8333(4) 0.4070(4) 0.2235(4) 0.0218(8) Uani 0.9771(7) 1 d . . P A 1
C10 C 0.8057(4) 0.5524(4) 0.2745(4) 0.0258(8) Uani 0.9771(7) 1 d . . P A 1
H10 H 0.810875 0.620198 0.221753 0.031 Uiso 0.9771(7) 1 calc R U P A 1
C11 C 0.7714(4) 0.6002(4) 0.3988(4) 0.0247(8) Uani 0.9771(7) 1 d . . P A 1
H11 H 0.752885 0.700397 0.431106 0.030 Uiso 0.9771(7) 1 calc R U P A 1
C12 C 0.8872(4) 0.2229(4) 0.0371(4) 0.0246(8) Uani 0.9771(7) 1 d . . P A 1
H12A H 0.794040 0.142678 0.035491 0.030 Uiso 0.9771(7) 1 calc R U P A 1
H12B H 0.982932 0.207454 0.089018 0.030 Uiso 0.9771(7) 1 calc R U P A 1
C13 C 0.9079(4) 0.2108(4) -0.1049(4) 0.0236(9) Uani 0.9771(7) 1 d . . P A 1
H13A H 0.811527 0.226948 -0.155280 0.028 Uiso 0.9771(7) 1 calc R U P A 1
H13B H 0.999487 0.293543 -0.101674 0.028 Uiso 0.9771(7) 1 calc R U P A 1
C14 C 0.9352(4) 0.0561(4) -0.1778(4) 0.0287(9) Uani 0.9771(7) 1 d . . P A 1
H14A H 0.848284 -0.026684 -0.173621 0.034 Uiso 0.9771(7) 1 calc R U P A 1
H14B H 1.036410 0.044127 -0.131303 0.034 Uiso 0.9771(7) 1 calc R U P A 1
C15 C 0.9424(18) 0.0359(15) -0.3259(9) 0.0360(14) Uani 0.9771(7) 1 d . . P A 1
H15A H 0.951545 -0.069146 -0.369808 0.054 Uiso 0.9771(7) 1 calc R U P A 1
H15B H 1.034996 0.110632 -0.330614 0.054 Uiso 0.9771(7) 1 calc R U P A 1
H15C H 0.845102 0.053511 -0.371355 0.054 Uiso 0.9771(7) 1 calc R U P A 1
I1 I 0.58150(3) 0.77342(2) 1.07385(2) 0.02400(7) Uani 0.9771(7) 1 d . . P A 1
I2 I 0.53973(3) 0.91983(3) 1.33316(3) 0.02967(8) Uani 0.9771(7) 1 d . . P A 1
N1 N 0.6320(3) 0.6555(3) 0.8568(3) 0.0220(7) Uani 0.9771(7) 1 d . . P A 1
O1 O 0.8641(3) 0.3733(2) 0.0977(2) 0.0262(6) Uani 0.9771(7) 1 d . . P A 1
C6A C 0.740(11) 0.529(9) 0.555(6) 0.0205(8) Uani 0.0229(7) 1 d DG . P A 2
C11A C 0.811(11) 0.478(10) 0.655(9) 0.0233(8) Uani 0.0229(7) 1 d G . P A 2
H11A H 0.883033 0.413336 0.636029 0.028 Uiso 0.0229(7) 1 calc R U P A 2
C10A C 0.777(11) 0.522(11) 0.782(7) 0.0235(8) Uani 0.0229(7) 1 d G . P A 2
H10A H 0.825423 0.486927 0.850484 0.028 Uiso 0.0229(7) 1 calc R U P A 2
C9A C 0.672(9) 0.616(8) 0.810(5) 0.0220(7) Uani 0.0229(7) 1 d DG . P A 2
C8A C 0.601(10) 0.667(10) 0.710(8) 0.0246(8) Uani 0.0229(7) 1 d G . P A 2
H8A H 0.529417 0.732127 0.728393 0.030 Uiso 0.0229(7) 1 calc R U P A 2
C7A C 0.635(13) 0.624(12) 0.582(6) 0.0251(8) Uani 0.0229(7) 1 d G . P A 2
H7A H 0.587026 0.658538 0.513936 0.030 Uiso 0.0229(7) 1 calc R U P A 2
C12A C 0.623(9) 0.690(9) 1.035(5) 0.02400(7) Uani 0.0229(7) 1 d D . P A 2
H12C H 0.737215 0.734324 1.076547 0.029 Uiso 0.0229(7) 1 calc R U P A 2
H12D H 0.594371 0.583538 1.040447 0.029 Uiso 0.0229(7) 1 calc R U P A 2
C13A C 0.523(10) 0.788(9) 1.110(6) 0.02400(7) Uani 0.0229(7) 1 d D . P A 2
H13C H 0.557932 0.895953 1.111062 0.029 Uiso 0.0229(7) 1 calc R U P A 2
H13D H 0.409666 0.748525 1.063376 0.029 Uiso 0.0229(7) 1 calc R U P A 2
C14A C 0.540(11) 0.782(10) 1.253(6) 0.02400(7) Uani 0.0229(7) 1 d D . P A 2
H14C H 0.653319 0.824109 1.299220 0.029 Uiso 0.0229(7) 1 calc R U P A 2
H14D H 0.510525 0.672462 1.250443 0.029 Uiso 0.0229(7) 1 calc R U P A 2
C15A C 0.436(13) 0.873(12) 1.333(9) 0.02967(8) Uani 0.0229(7) 1 d D . P A 2
H15D H 0.436685 0.968496 1.310133 0.045 Uiso 0.0229(7) 1 calc R U P A 2
H15E H 0.478776 0.899100 1.429440 0.045 Uiso 0.0229(7) 1 calc R U P A 2
H15F H 0.326840 0.810260 1.310850 0.045 Uiso 0.0229(7) 1 calc R U P A 2
I1A I 0.8848(15) 0.1922(15) -0.0520(14) 0.0236(9) Uani 0.0229(7) 1 d D . P A 2
I2A I 0.935(6) 0.047(5) -0.306(3) 0.0360(14) Uani 0.0229(7) 1 d D . P A 2
N1A N 0.844(12) 0.336(10) 0.173(5) 0.0218(8) Uani 0.0229(7) 1 d DG . P A 2
C1A C 0.821(14) 0.485(10) 0.214(7) 0.0258(8) Uani 0.0229(7) 1 d G . P A 2
H1A H 0.827500 0.546483 0.156319 0.031 Uiso 0.0229(7) 1 calc R U P A 2
C2A C 0.787(15) 0.543(9) 0.340(9) 0.0247(8) Uani 0.0229(7) 1 d G . P A 2
H2A H 0.770207 0.644194 0.368327 0.030 Uiso 0.0229(7) 1 calc R U P A 2
C3A C 0.776(15) 0.452(13) 0.425(6) 0.0207(8) Uani 0.0229(7) 1 d DG . P A 2
C4A C 0.800(15) 0.304(12) 0.383(8) 0.0233(8) Uani 0.0229(7) 1 d G . P A 2
H4A H 0.793270 0.241666 0.440854 0.028 Uiso 0.0229(7) 1 calc R U P A 2
C5A C 0.834(14) 0.245(9) 0.257(9) 0.0245(8) Uani 0.0229(7) 1 d G . P A 2
H5A H 0.850564 0.143952 0.228845 0.029 Uiso 0.0229(7) 1 calc R U P A 2
O1A O 0.595(8) 0.686(8) 0.901(5) 0.0220(7) Uani 0.0229(7) 1 d 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
C1 H1 0.9500 . ?
C1 C2 1.377(5) . ?
C1 N1 1.333(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(5) . ?
C3 C4 1.402(5) . ?
C3 C6 1.459(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9500 . ?
C5 N1 1.334(4) . ?
C6 C7 1.393(5) . ?
C6 C11 1.411(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(4) . ?
C9 C10 1.387(5) . ?
C9 O1 1.359(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(5) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.517(5) . ?
C12 O1 1.430(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.509(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.540(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
I1 I2 2.8143(4) . ?
I1 N1 2.398(3) . ?
C6A C11A 1.3900 . ?
C6A C7A 1.3900 . ?
C6A C3A 1.47(2) . ?
C11A H11A 0.9500 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9500 . ?
C10A C9A 1.3900 . ?
C9A C8A 1.3900 . ?
C9A O1A 1.35(2) . ?
C8A H8A 0.9500 . ?
C8A C7A 1.3900 . ?
C7A H7A 0.9500 . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.52(2) . ?
C12A O1A 1.40(2) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A C14A 1.52(2) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C15A 1.54(2) . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
I1A I2A 2.786(19) . ?
I1A N1A 2.493(19) . ?
N1A C1A 1.3900 . ?
N1A C5A 1.3900 . ?
C1A H1A 0.9500 . ?
C1A C2A 1.3900 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.2 . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.5(3) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 116.0(3) . . ?
C2 C3 C6 122.8(3) . . ?
C4 C3 C6 121.2(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.4 . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 H5 119.4 . . ?
C7 C6 C3 123.2(3) . . ?
C7 C6 C11 116.7(3) . . ?
C11 C6 C3 120.1(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.1(3) . . ?
O1 C9 C8 125.6(3) . . ?
O1 C9 C10 115.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C6 C11 H11 119.4 . . ?
C10 C11 C6 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O1 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
O1 C12 C13 107.8(3) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.2(3) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.1(6) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 I1 I2 176.92(7) . . ?
C1 N1 C5 120.0(3) . . ?
C1 N1 I1 122.4(2) . . ?
C5 N1 I1 117.2(2) . . ?
C9 O1 C12 118.1(2) . . ?
C11A C6A C7A 120.0 . . ?
C11A C6A C3A 111(8) . . ?
C7A C6A C3A 129(8) . . ?
C6A C11A H11A 120.0 . . ?
C6A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
O1A C9A C10A 146(6) . . ?
O1A C9A C8A 94(6) . . ?
C9A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
H12C C12A H12D 108.3 . . ?
C13A C12A H12C 109.9 . . ?
C13A C12A H12D 109.9 . . ?
O1A C12A H12C 109.9 . . ?
O1A C12A H12D 109.9 . . ?
O1A C12A C13A 109(3) . . ?
C12A C13A H13C 109.7 . . ?
C12A C13A H13D 109.7 . . ?
H13C C13A H13D 108.2 . . ?
C14A C13A C12A 110(3) . . ?
C14A C13A H13C 109.7 . . ?
C14A C13A H13D 109.7 . . ?
C13A C14A H14C 109.1 . . ?
C13A C14A H14D 109.1 . . ?
C13A C14A C15A 113(3) . . ?
H14C C14A H14D 107.8 . . ?
C15A C14A H14C 109.1 . . ?
C15A C14A H14D 109.1 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
N1A I1A I2A 177(3) . . ?
C1A N1A I1A 128(5) . . ?
C1A N1A C5A 120.0 . . ?
C5A N1A I1A 112(5) . . ?
N1A C1A H1A 120.0 . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A C6A 114(8) . . ?
C4A C3A C6A 126(8) . . ?
C4A C3A C2A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
N1A C5A H5A 120.0 . . ?
C4A C5A N1A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C9A O1A C12A 124(4) . . ?

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
C1 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 C6 179.4(3) . . . . ?
C2 C1 N1 C5 0.1(5) . . . . ?
C2 C1 N1 I1 -172.1(2) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C2 C3 C6 C7 24.2(5) . . . . ?
C2 C3 C6 C11 -157.2(3) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C3 C6 C7 C8 176.6(3) . . . . ?
C3 C6 C11 C10 -176.9(3) . . . . ?
C4 C3 C6 C7 -155.4(3) . . . . ?
C4 C3 C6 C11 23.2(5) . . . . ?
C4 C5 N1 C1 0.2(5) . . . . ?
C4 C5 N1 I1 172.8(2) . . . . ?
C6 C3 C4 C5 -179.1(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C6 C11 C10 1.8(5) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C7 C8 C9 O1 -179.5(3) . . . . ?
C8 C9 C10 C11 -1.8(5) . . . . ?
C8 C9 O1 C12 3.5(5) . . . . ?
C9 C10 C11 C6 0.1(5) . . . . ?
C10 C9 O1 C12 -177.5(3) . . . . ?
C11 C6 C7 C8 -2.1(5) . . . . ?
C12 C13 C14 C15 175.1(7) . . . . ?
C13 C12 O1 C9 176.1(3) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
O1 C9 C10 C11 179.1(3) . . . . ?
O1 C12 C13 C14 179.3(3) . . . . ?
C6A C11A C10A C9A 0.0 . . . . ?
C6A C3A C4A C5A -180(12) . . . . ?
C11A C6A C7A C8A 0.00(6) . . . . ?
C11A C6A C3A C2A -148(6) . . . . ?
C11A C6A C3A C4A 31(11) . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C11A C10A C9A O1A 177(4) . . . . ?
C10A C9A C8A C7A 0.0 . . . . ?
C10A C9A O1A C12A 8(8) . . . . ?
C9A C8A C7A C6A 0.0 . . . . ?
C8A C9A O1A C12A -175(5) . . . . ?
C7A C6A C11A C10A 0.0 . . . . ?
C7A C6A C3A C2A 40(10) . . . . ?
C7A C6A C3A C4A -140(8) . . . . ?
C12A C13A C14A C15A -178(5) . . . . ?
C13A C12A O1A C9A 176(5) . . . . ?
I1A N1A C1A C2A 175(7) . . . . ?
I1A N1A C5A C4A -175(6) . . . . ?
N1A C1A C2A C3A 0.0 . . . . ?
C1A N1A C5A C4A 0.0 . . . . ?
C1A C2A C3A C6A 180(10) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C6A C11A C10A -172(7) . . . . ?
C3A C6A C7A C8A 171(8) . . . . ?
C3A C4A C5A N1A 0.0 . . . . ?
C5A N1A C1A C2A 0.0 . . . . ?
O1A C9A C8A C7A -178(2) . . . . ?
O1A C12A C13A C14A 175(5) . . . . ?

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
-1 0 0 0.0469 -0.9981 0.0007 0.0011 0.0138 -0.0789 -0.0261
1 0 0 0.0559 0.9981 -0.0007 -0.0011 -0.0138 0.0789 0.0261
0 1 0 0.1051 0.0006 0.9973 0.0005 0.0245 -0.0008 0.0780
1 -1 1 0.0700 0.9988 -0.9989 0.9968 0.0278 0.1059 -0.0489
0 -1 0 0.0964 -0.0006 -0.9973 -0.0005 -0.0245 0.0008 -0.0780
0 0 -1 0.0049 -0.0013 0.0009 -0.9984 -0.0660 -0.0262 -0.0030
0 0 1 0.0099 0.0013 -0.0009 0.9984 0.0660 0.0262 0.0030

_olex2_date_sample_data_collection 1386321692.84
_olex2_date_sample_submission    1385424000
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_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_dwb1369
_database_code_depnum_ccdc_archive 'CCDC 2123967'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Cl I N O'
_chemical_formula_sum            'C15 H17 Cl I N O'
_chemical_formula_weight         389.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H17 Cl1 I1 N1 O1'
_chemical_oxdiff_usercomment     'Linda E375C'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8428(3)
_cell_length_b                   8.7456(4)
_cell_length_c                   11.7685(6)
_cell_angle_alpha                81.274(4)
_cell_angle_beta                 82.709(4)
_cell_angle_gamma                72.451(4)
_cell_volume                     757.89(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4480
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.8330
_cell_measurement_theta_min      3.1110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.2305
_exptl_crystal_size_mid          0.1084
_exptl_crystal_size_min          0.0297
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8707
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.241
_diffrn_reflns_theta_max         28.196
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   26.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   27.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   85.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784    0.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   52.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   27.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega  -52.00   38.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  8 omega  -56.00   42.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -37.0000   90.0000 98
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0209388000
_diffrn_orient_matrix_UB_12      0.0235474000
_diffrn_orient_matrix_UB_13      -0.0592346000
_diffrn_orient_matrix_UB_21      -0.0014709000
_diffrn_orient_matrix_UB_22      0.0769648000
_diffrn_orient_matrix_UB_23      0.0130642000
_diffrn_orient_matrix_UB_31      0.0928655000
_diffrn_orient_matrix_UB_32      -0.0293806000
_diffrn_orient_matrix_UB_33      0.0081590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71071
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2898
_reflns_number_total             3180
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.091
_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     173
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0235
_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)+(0.0153P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.7717(3) 0.6128(3) 0.0775(2) 0.0192(6) Uani 1 1 d . . . . .
H1 H 0.891543 0.565270 0.091237 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6433(3) 0.5553(3) 0.1449(2) 0.0197(6) Uani 1 1 d . . . . .
H2 H 0.676871 0.470262 0.203077 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4623(3) 0.6240(3) 0.1266(2) 0.0166(5) Uani 1 1 d . . . . .
C4 C 0.4240(3) 0.7478(3) 0.0348(2) 0.0190(6) Uani 1 1 d . . . . .
H4 H 0.305677 0.795117 0.017501 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5582(3) 0.8004(3) -0.0298(2) 0.0187(6) Uani 1 1 d . . . . .
H5 H 0.529190 0.882822 -0.090329 0.022 Uiso 1 1 calc R U . . .
C6 C 0.3180(3) 0.5726(3) 0.1995(2) 0.0171(5) Uani 1 1 d . . . . .
C7 C 0.3453(3) 0.4171(3) 0.2574(2) 0.0167(5) Uani 1 1 d . . . . .
H7 H 0.458715 0.343379 0.250685 0.020 Uiso 1 1 calc R U . . .
C8 C 0.2078(3) 0.3696(3) 0.3249(2) 0.0190(6) Uani 1 1 d . . . . .
H8 H 0.228757 0.264908 0.362343 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0380(3) 0.4797(3) 0.3362(2) 0.0181(6) Uani 1 1 d . . . . .
C10 C 0.0105(3) 0.6368(3) 0.2822(2) 0.0187(6) Uani 1 1 d . . . . .
H10 H -0.101161 0.712160 0.292198 0.022 Uiso 1 1 calc R U . . .
C11 C 0.1470(3) 0.6815(3) 0.2141(2) 0.0181(6) Uani 1 1 d . . . . .
H11 H 0.125430 0.786351 0.176966 0.022 Uiso 1 1 calc R U . . .
C12 C -0.0948(3) 0.2852(3) 0.4494(2) 0.0223(6) Uani 1 1 d . . . . .
H12A H -0.008510 0.252662 0.506995 0.027 Uiso 1 1 calc R U . . .
H12B H -0.056142 0.210864 0.391519 0.027 Uiso 1 1 calc R U . . .
C13 C -0.2793(3) 0.2846(3) 0.5048(2) 0.0227(6) Uani 1 1 d . . . . .
H13A H -0.364359 0.319785 0.446314 0.027 Uiso 1 1 calc R U . . .
H13B H -0.316608 0.360622 0.561500 0.027 Uiso 1 1 calc R U . . .
C14 C -0.2819(3) 0.1186(3) 0.5627(2) 0.0277(7) Uani 1 1 d . . . . .
H14A H -0.193870 0.082317 0.619323 0.033 Uiso 1 1 calc R U . . .
H14B H -0.247519 0.043500 0.505387 0.033 Uiso 1 1 calc R U . . .
C15 C -0.4657(3) 0.1158(4) 0.6224(3) 0.0342(7) Uani 1 1 d . . . . .
H15A H -0.554014 0.154514 0.567288 0.051 Uiso 1 1 calc R U . . .
H15B H -0.496635 0.184023 0.683056 0.051 Uiso 1 1 calc R U . . .
H15C H -0.461922 0.007290 0.654425 0.051 Uiso 1 1 calc R U . . .
Cl1 Cl 1.20045(8) 0.93114(8) -0.22076(6) 0.02348(15) Uani 1 1 d . . . . .
I1 I 0.95145(2) 0.83098(2) -0.10915(2) 0.01774(6) Uani 1 1 d . . . . .
N1 N 0.7307(2) 0.7350(2) -0.00746(18) 0.0177(5) Uani 1 1 d . . . . .
O1 O -0.1087(2) 0.4478(2) 0.39693(15) 0.0235(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.370(3) . ?
C1 N1 1.340(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(3) . ?
C3 C4 1.400(3) . ?
C3 C6 1.470(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(3) . ?
C5 H5 0.9300 . ?
C5 N1 1.344(3) . ?
C6 C7 1.393(3) . ?
C6 C11 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(3) . ?
C9 C10 1.389(3) . ?
C9 O1 1.355(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.511(3) . ?
C12 O1 1.440(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.513(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.526(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Cl1 I1 2.5174(6) . ?
I1 N1 2.276(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.3(2) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 116.1(2) . . ?
C2 C3 C6 122.7(2) . . ?
C4 C3 C6 121.2(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.4 . . ?
N1 C5 C4 121.2(2) . . ?
N1 C5 H5 119.4 . . ?
C7 C6 C3 122.2(2) . . ?
C7 C6 C11 117.5(2) . . ?
C11 C6 C3 120.3(2) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 119.4(2) . . ?
O1 C9 C8 125.5(2) . . ?
O1 C9 C10 115.1(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O1 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
O1 C12 C13 106.75(19) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.6(2) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C13 C14 C15 112.7(2) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 I1 Cl1 178.74(5) . . ?
C1 N1 C5 118.9(2) . . ?
C1 N1 I1 119.95(15) . . ?
C5 N1 I1 121.13(17) . . ?
C9 O1 C12 118.68(18) . . ?

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
C1 C2 C3 C4 2.0(4) . . . . ?
C1 C2 C3 C6 -177.1(2) . . . . ?
C2 C1 N1 C5 -2.1(4) . . . . ?
C2 C1 N1 I1 176.91(19) . . . . ?
C2 C3 C4 C5 -2.0(4) . . . . ?
C2 C3 C6 C7 -27.5(4) . . . . ?
C2 C3 C6 C11 151.5(2) . . . . ?
C3 C4 C5 N1 0.0(4) . . . . ?
C3 C6 C7 C8 -179.3(2) . . . . ?
C3 C6 C11 C10 -179.6(2) . . . . ?
C4 C3 C6 C7 153.5(2) . . . . ?
C4 C3 C6 C11 -27.6(4) . . . . ?
C4 C5 N1 C1 2.1(4) . . . . ?
C4 C5 N1 I1 -176.90(18) . . . . ?
C6 C3 C4 C5 177.1(2) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C6 C11 C10 -0.6(4) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C7 C8 C9 O1 178.2(2) . . . . ?
C8 C9 C10 C11 2.8(4) . . . . ?
C8 C9 O1 C12 -4.0(4) . . . . ?
C9 C10 C11 C6 -1.7(4) . . . . ?
C10 C9 O1 C12 176.0(2) . . . . ?
C11 C6 C7 C8 1.7(4) . . . . ?
C12 C13 C14 C15 178.3(2) . . . . ?
C13 C12 O1 C9 -177.0(2) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
O1 C9 C10 C11 -177.1(2) . . . . ?
O1 C12 C13 C14 179.8(2) . . . . ?

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 -1 0 0.0420 -0.0003 -0.9979 -0.0011 -0.0234 -0.0768 0.0293
0 1 0 0.0620 0.0003 0.9979 0.0011 0.0234 0.0768 -0.0293
1 1 0 0.0689 0.9981 0.9982 0.0011 0.0443 0.0754 0.0634
0 0 -1 0.0148 0.0000 0.0005 -0.9981 0.0591 -0.0130 -0.0082
0 0 1 0.0148 -0.0000 -0.0005 0.9981 -0.0591 0.0130 0.0082
-2 -1 0 0.1057 -1.9959 -0.9985 -0.0011 -0.0652 -0.0739 -0.1560

_olex2_date_sample_data_collection 1386688337.27
_olex2_date_sample_submission    1384992000
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_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_dwb1329a
_database_code_depnum_ccdc_archive 'CCDC 2123970'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br3, C21 H30 N O'
_chemical_formula_sum            'C21 H30 Br3 N O'
_chemical_formula_weight         552.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H30 Br3 N1 O1'
_chemical_oxdiff_usercomment     'James JAT30 repeat'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.63873(14)
_cell_length_b                   56.6665(12)
_cell_length_c                   8.4248(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.637(2)
_cell_angle_gamma                90
_cell_volume                     2203.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4362
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.2120
_cell_measurement_theta_min      2.8690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.502
_exptl_absorpt_correction_T_max  0.567
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.3087
_exptl_crystal_size_mid          0.1563
_exptl_crystal_size_min          0.1294
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -79
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10718
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         3.022
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   52.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       33.6389  -99.0000  120.0000 136

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   83.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       33.6389  -99.0000 -180.0000 200

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   69.00   0.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       33.6389  -37.0000 -120.0000 168
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1348453000
_diffrn_orient_matrix_UB_12      -0.0034585000
_diffrn_orient_matrix_UB_13      -0.0402544000
_diffrn_orient_matrix_UB_21      0.0728677000
_diffrn_orient_matrix_UB_22      -0.0077606000
_diffrn_orient_matrix_UB_23      -0.0487117000
_diffrn_orient_matrix_UB_31      -0.0108274000
_diffrn_orient_matrix_UB_32      -0.0091933000
_diffrn_orient_matrix_UB_33      0.0562289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5350
_reflns_number_total             6356
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.682
_refine_diff_density_min         -1.870
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         6356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.191
_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)+(0.0128P)²+5.5741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          
;
The N-H hydrogen was found by difference map after all other atoms
had been located and refined.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.36412(10) 0.23334(2) 0.97718(7) 0.02758(12) Uani 1 1 d . . . . .
Br2 Br 1.08444(9) 0.19236(2) 0.95288(5) 0.01901(10) Uani 1 1 d . . . . .
Br3 Br 0.81422(10) 0.15546(2) 0.92307(5) 0.02291(10) Uani 1 1 d . . . . .
C1 C 0.8693(10) 0.28876(8) 0.8403(6) 0.0254(10) Uani 1 1 d . . . . .
H1 H 0.969819 0.283461 0.754002 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7014(10) 0.30861(8) 0.8227(6) 0.0235(9) Uani 1 1 d . . . . .
H2 H 0.685722 0.316942 0.724390 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5512(8) 0.31677(7) 0.9500(5) 0.0161(8) Uani 1 1 d . . . . .
C4 C 0.5809(10) 0.30330(7) 1.0896(5) 0.0214(9) Uani 1 1 d . . . . .
H4 H 0.481618 0.307940 1.177891 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7513(10) 0.28346(8) 1.1010(6) 0.0240(9) Uani 1 1 d . . . . .
H5 H 0.768604 0.274455 1.196632 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3705(8) 0.33813(7) 0.9341(5) 0.0154(8) Uani 1 1 d . . . . .
C7 C 0.3363(9) 0.35124(7) 0.7910(5) 0.0195(8) Uani 1 1 d . . . . .
H7 H 0.435971 0.346332 0.703430 0.023 Uiso 1 1 calc R U . . .
C8 C 0.1635(9) 0.37081(8) 0.7751(5) 0.0203(8) Uani 1 1 d . . . . .
H8 H 0.143134 0.379211 0.677043 0.024 Uiso 1 1 calc R U . . .
C9 C 0.0172(9) 0.37848(7) 0.9024(5) 0.0169(8) Uani 1 1 d . . . . .
C10 C 0.0489(9) 0.36634(7) 1.0464(5) 0.0185(8) Uani 1 1 d . . . . .
H10 H -0.048075 0.371607 1.134151 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2234(9) 0.34649(7) 1.0605(5) 0.0188(8) Uani 1 1 d . . . . .
H11 H 0.244237 0.338251 1.159154 0.023 Uiso 1 1 calc R U . . .
C12 C -0.3058(9) 0.40673(7) 0.9995(5) 0.0180(8) Uani 1 1 d . . . . .
H12A H -0.170483 0.412012 1.090819 0.022 Uiso 1 1 calc R U . . .
H12B H -0.430711 0.394120 1.036655 0.022 Uiso 1 1 calc R U . . .
C13 C -0.4886(9) 0.42723(7) 0.9322(5) 0.0198(8) Uani 1 1 d . . . . .
H13A H -0.616960 0.432379 1.012779 0.024 Uiso 1 1 calc R U . . .
H13B H -0.613446 0.421707 0.837377 0.024 Uiso 1 1 calc R U . . .
C14 C -0.3132(9) 0.44835(7) 0.8846(5) 0.0191(8) Uani 1 1 d . . . . .
H14A H -0.184067 0.453627 0.978472 0.023 Uiso 1 1 calc R U . . .
H14B H -0.189511 0.443374 0.801346 0.023 Uiso 1 1 calc R U . . .
C15 C -0.5003(9) 0.46901(7) 0.8220(5) 0.0197(8) Uani 1 1 d . . . . .
H15A H -0.627041 0.463762 0.727229 0.024 Uiso 1 1 calc R U . . .
H15B H -0.626558 0.473750 0.904691 0.024 Uiso 1 1 calc R U . . .
C16 C -0.3289(9) 0.49030(7) 0.7770(5) 0.0201(9) Uani 1 1 d . . . . .
H16A H -0.205143 0.485621 0.692991 0.024 Uiso 1 1 calc R U . . .
H16B H -0.199599 0.495370 0.871279 0.024 Uiso 1 1 calc R U . . .
C17 C -0.5155(9) 0.51117(7) 0.7169(5) 0.0204(9) Uani 1 1 d . . . . .
H17A H -0.644459 0.515487 0.799218 0.025 Uiso 1 1 calc R U . . .
H17B H -0.639631 0.506283 0.620160 0.025 Uiso 1 1 calc R U . . .
C18 C -0.3423(9) 0.53290(8) 0.6772(6) 0.0220(9) Uani 1 1 d . . . . .
H18A H -0.214293 0.537550 0.773048 0.026 Uiso 1 1 calc R U . . .
H18B H -0.217438 0.528722 0.592655 0.026 Uiso 1 1 calc R U . . .
C19 C -0.5293(9) 0.55384(7) 0.6217(6) 0.0212(9) Uani 1 1 d . . . . .
H19A H -0.667426 0.557086 0.701386 0.025 Uiso 1 1 calc R U . . .
H19B H -0.643280 0.549750 0.519841 0.025 Uiso 1 1 calc R U . . .
C20 C -0.3546(10) 0.57603(8) 0.5978(6) 0.0242(9) Uani 1 1 d . . . . .
H20A H -0.233783 0.579656 0.698266 0.029 Uiso 1 1 calc R U . . .
H20B H -0.222578 0.572950 0.514644 0.029 Uiso 1 1 calc R U . . .
C21 C -0.5399(11) 0.59741(8) 0.5492(6) 0.0287(10) Uani 1 1 d . . . . .
H21A H -0.678148 0.600125 0.628042 0.043 Uiso 1 1 calc R U . . .
H21B H -0.645711 0.594592 0.444371 0.043 Uiso 1 1 calc R U . . .
H21C H -0.415489 0.611300 0.543659 0.043 Uiso 1 1 calc R U . . .
N1 N 0.8936(8) 0.27675(6) 0.9772(5) 0.0211(8) Uani 1 1 d . . . . .
H1A H 1.017(11) 0.2633(9) 0.995(7) 0.037(16) Uiso 1 1 d . . . . .
O1 O -0.1481(6) 0.39819(5) 0.8732(3) 0.0182(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Br2 2.6584(6) . ?
Br2 Br3 2.4381(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.367(6) . ?
C1 N1 1.335(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.413(6) . ?
C3 C4 1.397(6) . ?
C3 C6 1.471(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(6) . ?
C5 H5 0.9500 . ?
C5 N1 1.343(6) . ?
C6 C7 1.412(6) . ?
C6 C11 1.402(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.367(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(6) . ?
C9 C10 1.390(6) . ?
C9 O1 1.363(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(6) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.515(6) . ?
C12 O1 1.434(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.523(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.521(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.514(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.523(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.525(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.520(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.518(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 H1A 0.96(5) . ?

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
Br3 Br2 Br1 177.79(2) . . ?
C2 C1 H1 119.6 . . ?
N1 C1 H1 119.6 . . ?
N1 C1 C2 120.8(4) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C6 121.3(4) . . ?
C4 C3 C2 116.4(4) . . ?
C4 C3 C6 122.3(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.0 . . ?
N1 C5 C4 120.0(4) . . ?
N1 C5 H5 120.0 . . ?
C7 C6 C3 121.7(4) . . ?
C11 C6 C3 121.6(4) . . ?
C11 C6 C7 116.6(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.0(4) . . ?
O1 C9 C8 115.1(4) . . ?
O1 C9 C10 124.9(4) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C6 C11 H11 118.9 . . ?
C10 C11 C6 122.3(4) . . ?
C10 C11 H11 118.9 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O1 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
O1 C12 C13 106.8(3) . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C12 C13 C14 114.0(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.3(3) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.9(3) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 C17 114.0(3) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C16 C17 C18 113.9(3) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.7(4) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 113.1(4) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.6(4) . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C5 121.4(4) . . ?
C1 N1 H1A 123(3) . . ?
C5 N1 H1A 116(3) . . ?
C9 O1 C12 117.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Br1 0.96(5) 2.35(5) 3.289(4) 165(5) . yes

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
C1 C2 C3 C4 -1.2(7) . . . . ?
C1 C2 C3 C6 179.7(4) . . . . ?
C2 C1 N1 C5 1.1(7) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C2 C3 C6 C7 0.7(6) . . . . ?
C2 C3 C6 C11 -179.3(4) . . . . ?
C3 C4 C5 N1 0.2(7) . . . . ?
C3 C6 C7 C8 178.6(4) . . . . ?
C3 C6 C11 C10 -178.9(4) . . . . ?
C4 C3 C6 C7 -178.3(4) . . . . ?
C4 C3 C6 C11 1.7(6) . . . . ?
C4 C5 N1 C1 -1.3(7) . . . . ?
C6 C3 C4 C5 -179.9(4) . . . . ?
C6 C7 C8 C9 0.6(7) . . . . ?
C7 C6 C11 C10 1.1(6) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C7 C8 C9 O1 179.9(4) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C8 C9 O1 C12 179.4(4) . . . . ?
C9 C10 C11 C6 0.0(6) . . . . ?
C10 C9 O1 C12 -1.4(6) . . . . ?
C11 C6 C7 C8 -1.4(6) . . . . ?
C12 C13 C14 C15 -178.3(4) . . . . ?
C13 C12 O1 C9 -175.3(3) . . . . ?
C13 C14 C15 C16 179.0(4) . . . . ?
C14 C15 C16 C17 -179.0(4) . . . . ?
C15 C16 C17 C18 177.9(4) . . . . ?
C16 C17 C18 C19 -178.5(4) . . . . ?
C17 C18 C19 C20 174.5(4) . . . . ?
C18 C19 C20 C21 -177.5(4) . . . . ?
N1 C1 C2 C3 0.2(7) . . . . ?
O1 C9 C10 C11 179.9(4) . . . . ?
O1 C12 C13 C14 -64.8(5) . . . . ?

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 1 0 0.0742 0.0001 1.0000 -0.0000 -0.0035 -0.0078 -0.0092
0 -1 0 0.0552 -0.0001 -1.0000 0.0000 0.0035 0.0078 0.0092
0 3 -1 0.1114 -0.0001 2.9978 -1.0000 0.0299 0.0254 -0.0838
1 1 0 0.1080 1.0004 1.0011 -0.0001 -0.1384 0.0651 -0.0200
-1 0 -1 0.0610 -1.0007 -0.0032 -0.9998 0.1752 -0.0242 -0.0454
0 -4 1 0.0962 -0.0000 -3.9978 1.0001 -0.0264 -0.0177 0.0930
0 5 1 0.0798 0.0009 5.0022 0.9997 -0.0577 -0.0875 0.0102
0 -5 -1 0.1050 -0.0009 -5.0022 -0.9997 0.0577 0.0875 -0.0102
1 1 1 0.0916 1.0008 1.0032 0.9998 -0.1787 0.0164 0.0362
0 -1 -2 0.0911 -0.0009 -1.0044 -1.9998 0.0841 0.1051 -0.1032

_olex2_date_sample_data_collection 1368694594.59
_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_dwb1347
_database_code_depnum_ccdc_archive 'CCDC 2123973'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C19 H26 N O'
_chemical_formula_sum            'C19 H26 Br N O'
_chemical_formula_weight         364.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H26 Br1 N1 O1'
_chemical_oxdiff_usercomment     LJM387
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7554(3)
_cell_length_b                   8.4116(3)
_cell_length_c                   16.8284(7)
_cell_angle_alpha                97.564(3)
_cell_angle_beta                 96.503(4)
_cell_angle_gamma                110.294(4)
_cell_volume                     876.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3862
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.2930
_cell_measurement_theta_min      3.0950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.3026
_exptl_crystal_size_mid          0.1694
_exptl_crystal_size_min          0.0344
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7701
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.081
_diffrn_reflns_theta_min         3.103
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -35.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0110 -178.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00  -13.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.0110  127.0000 -142.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   81.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735 -127.0000  141.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   48.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735  -57.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   71.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       26.5735  -19.0000   30.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0147792000
_diffrn_orient_matrix_UB_12      0.0119242000
_diffrn_orient_matrix_UB_13      0.0430793000
_diffrn_orient_matrix_UB_21      0.0759725000
_diffrn_orient_matrix_UB_22      -0.0407650000
_diffrn_orient_matrix_UB_23      -0.0001228000
_diffrn_orient_matrix_UB_31      0.0831803000
_diffrn_orient_matrix_UB_32      0.0809951000
_diffrn_orient_matrix_UB_33      0.0025327000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4436
_reflns_number_total             5098
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         5098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.1907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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 0.94513(3) 0.80938(2) 0.57280(2) 0.01853(6) Uani 1 1 d . . . . .
C1 C -0.5150(3) 0.0541(3) 0.60897(13) 0.0238(4) Uani 1 1 d . . . . .
H1 H -0.612236 -0.045799 0.620534 0.029 Uiso 1 1 calc R U . . .
C2 C -0.3035(3) 0.1087(3) 0.64265(13) 0.0223(4) Uani 1 1 d . . . . .
H2 H -0.258222 0.044469 0.676433 0.027 Uiso 1 1 calc R U . . .
C3 C -0.1536(3) 0.2601(2) 0.62709(11) 0.0157(4) Uani 1 1 d . . . . .
C4 C -0.2331(3) 0.3479(3) 0.57470(13) 0.0217(4) Uani 1 1 d . . . . .
H4 H -0.140138 0.448391 0.561989 0.026 Uiso 1 1 calc R U . . .
C5 C -0.4461(3) 0.2880(3) 0.54181(13) 0.0245(4) Uani 1 1 d . . . . .
H5 H -0.496303 0.347959 0.506950 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0735(3) 0.3238(2) 0.66513(11) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.1472(3) 0.2358(2) 0.71927(12) 0.0196(4) Uani 1 1 d . . . . .
H7 H 0.051954 0.133555 0.729623 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3568(3) 0.2969(2) 0.75747(12) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.400887 0.236326 0.793664 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5040(3) 0.4486(2) 0.74259(11) 0.0166(4) Uani 1 1 d . . . . .
C10 C 0.4361(3) 0.5375(2) 0.68818(12) 0.0189(4) Uani 1 1 d . . . . .
H10 H 0.532698 0.638188 0.677051 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2238(3) 0.4753(2) 0.65061(12) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.179806 0.536250 0.614592 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8661(3) 0.6526(2) 0.77373(12) 0.0193(4) Uani 1 1 d . . . . .
H12A H 0.822755 0.749230 0.789210 0.023 Uiso 1 1 calc R U . . .
H12B H 0.885725 0.647039 0.717357 0.023 Uiso 1 1 calc R U . . .
C13 C 1.0711(3) 0.6749(2) 0.82735(12) 0.0189(4) Uani 1 1 d . . . . .
H13A H 1.117133 0.581095 0.809223 0.023 Uiso 1 1 calc R U . . .
H13B H 1.046126 0.670141 0.882776 0.023 Uiso 1 1 calc R U . . .
C14 C 1.2474(3) 0.8462(2) 0.82554(12) 0.0193(4) Uani 1 1 d . . . . .
H14A H 1.268799 0.850904 0.769742 0.023 Uiso 1 1 calc R U . . .
H14B H 1.200199 0.939125 0.843987 0.023 Uiso 1 1 calc R U . . .
C15 C 1.4605(3) 0.8757(2) 0.87774(12) 0.0186(4) Uani 1 1 d . . . . .
H15A H 1.438231 0.862121 0.932769 0.022 Uiso 1 1 calc R U . . .
H15B H 1.515264 0.789363 0.856451 0.022 Uiso 1 1 calc R U . . .
C16 C 1.6252(3) 1.0541(2) 0.87968(12) 0.0192(4) Uani 1 1 d . . . . .
H16A H 1.568939 1.138974 0.901667 0.023 Uiso 1 1 calc R U . . .
H16B H 1.641245 1.067586 0.824126 0.023 Uiso 1 1 calc R U . . .
C17 C 1.8465(3) 1.0953(2) 0.92863(12) 0.0203(4) Uani 1 1 d . . . . .
H17A H 1.832936 1.077712 0.983895 0.024 Uiso 1 1 calc R U . . .
H17B H 1.910064 1.017284 0.904809 0.024 Uiso 1 1 calc R U . . .
C18 C 1.9918(3) 1.2804(3) 0.93011(14) 0.0257(4) Uani 1 1 d . . . . .
H18A H 1.996558 1.298521 0.874503 0.031 Uiso 1 1 calc R U . . .
H18B H 1.929643 1.357188 0.956106 0.031 Uiso 1 1 calc R U . . .
C19 C 2.2196(3) 1.3290(3) 0.97409(16) 0.0337(5) Uani 1 1 d . . . . .
H19A H 2.281937 1.252169 0.949666 0.051 Uiso 1 1 calc R U . . .
H19B H 2.217905 1.320197 1.030334 0.051 Uiso 1 1 calc R U . . .
H19C H 2.302832 1.445205 0.970065 0.051 Uiso 1 1 calc R U . . .
N1 N -0.5829(3) 0.1434(2) 0.55956(11) 0.0223(4) Uani 1 1 d . . . . .
H1A H -0.717(5) 0.109(4) 0.5399(19) 0.059(9) Uiso 1 1 d . . . . .
O1 O 0.7060(2) 0.49514(17) 0.78372(8) 0.0206(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.366(3) . ?
C1 N1 1.335(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.403(3) . ?
C3 C4 1.397(3) . ?
C3 C6 1.472(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(3) . ?
C5 H5 0.9300 . ?
C5 N1 1.342(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.398(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(3) . ?
C9 C10 1.390(3) . ?
C9 O1 1.356(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.503(3) . ?
C12 O1 1.435(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.524(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.521(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.523(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.521(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.519(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 H1A 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.8 . . ?
N1 C1 H1 119.8 . . ?
N1 C1 C2 120.39(19) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.07(19) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C6 121.73(17) . . ?
C4 C3 C2 116.12(18) . . ?
C4 C3 C6 122.14(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.91(19) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.8 . . ?
N1 C5 C4 120.42(19) . . ?
N1 C5 H5 119.8 . . ?
C7 C6 C3 120.82(16) . . ?
C11 C6 C3 122.18(17) . . ?
C11 C6 C7 116.99(17) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.53(17) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.68(18) . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.05(17) . . ?
O1 C9 C8 115.13(17) . . ?
O1 C9 C10 125.81(16) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.69(17) . . ?
C11 C10 H10 120.2 . . ?
C6 C11 H11 119.0 . . ?
C10 C11 C6 122.05(18) . . ?
C10 C11 H11 119.0 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
O1 C12 H12A 110.2 . . ?
O1 C12 H12B 110.2 . . ?
O1 C12 C13 107.57(15) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.38(16) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.05(16) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.04(16) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
C15 C16 C17 116.24(16) . . ?
H16A C16 H16B 107.4 . . ?
C17 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.16(17) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.44(19) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C5 121.08(18) . . ?
C1 N1 H1A 119(2) . . ?
C5 N1 H1A 120(2) . . ?
C9 O1 C12 118.69(15) . . ?

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
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C6 177.87(19) . . . . ?
C2 C1 N1 C5 0.0(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C3 C6 C7 -0.8(3) . . . . ?
C2 C3 C6 C11 -179.41(19) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C6 C7 C8 -177.63(19) . . . . ?
C3 C6 C11 C10 178.21(18) . . . . ?
C4 C3 C6 C7 178.05(19) . . . . ?
C4 C3 C6 C11 -0.6(3) . . . . ?
C4 C5 N1 C1 -0.5(3) . . . . ?
C6 C3 C4 C5 -178.31(19) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C7 C6 C11 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 O1 -179.79(19) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C8 C9 O1 C12 -178.15(17) . . . . ?
C9 C10 C11 C6 -0.4(3) . . . . ?
C10 C9 O1 C12 2.3(3) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
C12 C13 C14 C15 -179.19(17) . . . . ?
C13 C12 O1 C9 178.48(16) . . . . ?
C13 C14 C15 C16 -175.11(17) . . . . ?
C14 C15 C16 C17 -178.48(17) . . . . ?
C15 C16 C17 C18 -176.54(17) . . . . ?
C16 C17 C18 C19 -176.95(18) . . . . ?
N1 C1 C2 C3 0.8(3) . . . . ?
O1 C9 C10 C11 -179.68(18) . . . . ?
O1 C12 C13 C14 -175.85(16) . . . . ?

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 0 1 0.0232 0.0000 0.0003 0.9999 0.0431 -0.0001 0.0026
0 0 -1 0.0112 -0.0000 -0.0003 -0.9999 -0.0431 0.0001 -0.0026
0 -1 0 0.0801 0.0006 -1.0002 0.0013 -0.0119 0.0408 -0.0810
0 1 0 0.0801 -0.0006 1.0002 -0.0013 0.0119 -0.0408 0.0810
1 0 0 0.1103 1.0000 -0.0003 -0.0008 0.0147 0.0760 0.0832
-1 0 0 0.1103 -1.0000 0.0003 0.0008 -0.0147 -0.0760 -0.0832

_olex2_date_sample_data_collection 1380538994.0
_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_dwb1416
_database_code_depnum_ccdc_archive 'CCDC 2123969'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Br I N O'
_chemical_formula_sum            'C15 H17 Br I N O'
_chemical_formula_weight         434.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H17 Br1 N1 O1 I1'
_chemical_oxdiff_usercomment     'Linda E404D'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0323(4)
_cell_length_b                   11.3017(4)
_cell_length_c                   15.5236(5)
_cell_angle_alpha                106.418(3)
_cell_angle_beta                 94.206(3)
_cell_angle_gamma                113.861(4)
_cell_volume                     1508.27(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      28.0000
_cell_measurement_theta_min      3.4300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.764
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1594
_exptl_crystal_size_mid          0.0847
_exptl_crystal_size_min          0.0145
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         2.801
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   24.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9940  -99.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   38.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -57.0000  -90.0000 63

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   89.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   37.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   85.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784   19.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   57.00   1.0000  112.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4784  -99.0000 -150.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0263250000
_diffrn_orient_matrix_UB_12      -0.0479414000
_diffrn_orient_matrix_UB_13      -0.0218054000
_diffrn_orient_matrix_UB_21      -0.0682988000
_diffrn_orient_matrix_UB_22      -0.0550552000
_diffrn_orient_matrix_UB_23      -0.0012831000
_diffrn_orient_matrix_UB_31      -0.0300954000
_diffrn_orient_matrix_UB_32      -0.0023768000
_diffrn_orient_matrix_UB_33      -0.0435972000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5105
_reflns_number_total             6069
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.045
_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)+(0.0119P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C27(H27a,H27b), C28(H28a,
 H28b), C29(H29a,H29b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C30(H30a,H30b,H30c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.71744(4) 0.03930(4) 0.63718(2) 0.02030(9) Uani 1 1 d . . . . .
C1 C 0.6145(3) 0.3040(3) 0.3862(2) 0.0145(7) Uani 1 1 d . . . . .
H1 H 0.522177 0.258296 0.399187 0.017 Uiso 1 1 calc R U . . .
C2 C 0.6261(3) 0.3805(3) 0.3305(2) 0.0156(8) Uani 1 1 d . . . . .
H2 H 0.542143 0.386569 0.306895 0.019 Uiso 1 1 calc R U . . .
C3 C 0.7622(3) 0.4497(3) 0.3084(2) 0.0143(8) Uani 1 1 d . . . . .
C4 C 0.8835(4) 0.4346(4) 0.3466(2) 0.0208(8) Uani 1 1 d . . . . .
H4 H 0.976894 0.477035 0.333778 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8636(4) 0.3573(4) 0.4028(2) 0.0225(9) Uani 1 1 d . . . . .
H5 H 0.945228 0.349303 0.428086 0.027 Uiso 1 1 calc R U . . .
C6 C 0.7806(3) 0.5324(3) 0.2482(2) 0.0129(7) Uani 1 1 d . . . . .
C7 C 0.6574(3) 0.5285(4) 0.1970(2) 0.0159(8) Uani 1 1 d . . . . .
H7 H 0.562257 0.475003 0.203130 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6725(4) 0.6011(3) 0.1379(2) 0.0156(8) Uani 1 1 d . . . . .
H8 H 0.588341 0.596497 0.104839 0.019 Uiso 1 1 calc R U . . .
C9 C 0.8138(4) 0.6817(4) 0.1277(2) 0.0149(8) Uani 1 1 d . . . . .
C10 C 0.9387(3) 0.6909(4) 0.1803(2) 0.0167(8) Uani 1 1 d . . . . .
H10 H 1.033839 0.746592 0.175330 0.020 Uiso 1 1 calc R U . . .
C11 C 0.9219(3) 0.6181(3) 0.2391(2) 0.0150(8) Uani 1 1 d . . . . .
H11 H 1.006355 0.625828 0.273972 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7202(4) 0.7600(4) 0.0194(2) 0.0186(8) Uani 1 1 d . . . . .
H12A H 0.679206 0.810260 0.061703 0.022 Uiso 1 1 calc R U . . .
H12B H 0.641770 0.668140 -0.014057 0.022 Uiso 1 1 calc R U . . .
C13 C 0.7823(3) 0.8333(4) -0.0460(2) 0.0157(8) Uani 1 1 d . . . . .
H13A H 0.814038 0.776714 -0.090846 0.019 Uiso 1 1 calc R U . . .
H13B H 0.869990 0.918598 -0.011855 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6749(3) 0.8664(4) -0.0967(2) 0.0181(8) Uani 1 1 d . . . . .
H14A H 0.654429 0.934625 -0.053599 0.022 Uiso 1 1 calc R U . . .
H14B H 0.581414 0.783939 -0.124840 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7407(4) 0.9214(4) -0.1707(2) 0.0181(8) Uani 1 1 d . . . . .
H15A H 0.755050 0.851576 -0.215364 0.027 Uiso 1 1 calc R U . . .
H15B H 0.834932 1.001020 -0.142974 0.027 Uiso 1 1 calc R U . . .
H15C H 0.673665 0.946186 -0.200204 0.027 Uiso 1 1 calc R U . . .
I1 I 0.71910(2) 0.17282(2) 0.52171(2) 0.01471(6) Uani 1 1 d . . . . .
N1 N 0.7322(3) 0.2931(3) 0.42251(18) 0.0155(6) Uani 1 1 d . . . . .
O1 O 0.8430(2) 0.7531(2) 0.06868(15) 0.0180(6) Uani 1 1 d . . . . .
Br2 Br 0.25741(4) 0.45023(4) 0.28677(2) 0.02080(9) Uani 1 1 d . . . . .
C16 C 0.3831(4) 0.2679(4) 0.5801(2) 0.0182(8) Uani 1 1 d . . . . .
H16 H 0.473228 0.321124 0.567928 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3838(4) 0.2012(4) 0.6409(2) 0.0173(8) Uani 1 1 d . . . . .
H17 H 0.474127 0.211674 0.670151 0.021 Uiso 1 1 calc R U . . .
C18 C 0.2518(4) 0.1181(4) 0.6598(2) 0.0152(8) Uani 1 1 d . . . . .
C19 C 0.1210(3) 0.1124(4) 0.6157(2) 0.0171(8) Uani 1 1 d . . . . .
H19 H 0.029194 0.060220 0.626689 0.021 Uiso 1 1 calc R U . . .
C20 C 0.1283(4) 0.1832(4) 0.5566(2) 0.0182(8) Uani 1 1 d . . . . .
H20 H 0.040409 0.178719 0.528467 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2459(3) 0.0382(3) 0.7208(2) 0.0141(7) Uani 1 1 d . . . . .
C22 C 0.3691(3) 0.0164(4) 0.7472(2) 0.0173(8) Uani 1 1 d . . . . .
H22 H 0.455711 0.053821 0.725984 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3640(4) -0.0587(4) 0.8032(2) 0.0194(8) Uani 1 1 d . . . . .
H23 H 0.447259 -0.070889 0.819960 0.023 Uiso 1 1 calc R U . . .
C24 C 0.2359(4) -0.1172(4) 0.8354(2) 0.0163(8) Uani 1 1 d . . . . .
C25 C 0.1127(3) -0.0972(3) 0.8114(2) 0.0169(8) Uani 1 1 d . . . . .
H25 H 0.026473 -0.135391 0.832736 0.020 Uiso 1 1 calc R U . . .
C26 C 0.1194(3) -0.0202(4) 0.7556(2) 0.0174(8) Uani 1 1 d . . . . .
H26 H 0.036691 -0.006392 0.740452 0.021 Uiso 1 1 calc R U . . .
C27 C 0.1168(4) -0.2507(4) 0.9276(2) 0.0211(8) Uani 1 1 d . . . . .
H27A H 0.027368 -0.306781 0.879353 0.025 Uiso 1 1 calc R U . . .
H27B H 0.102156 -0.177968 0.970312 0.025 Uiso 1 1 calc R U . . .
C28 C 0.1457(4) -0.3375(4) 0.9768(2) 0.0204(8) Uani 1 1 d . . . . .
H28A H 0.155963 -0.411528 0.932337 0.024 Uiso 1 1 calc R U . . .
H28B H 0.059258 -0.379023 1.001513 0.024 Uiso 1 1 calc R U . . .
C29 C 0.2832(4) -0.2612(4) 1.0547(2) 0.0232(9) Uani 1 1 d . . . . .
H29A H 0.276446 -0.184375 1.098388 0.028 Uiso 1 1 calc R U . . .
H29B H 0.371416 -0.224694 1.030182 0.028 Uiso 1 1 calc R U . . .
C30 C 0.2985(4) -0.3566(4) 1.1043(2) 0.0273(9) Uani 1 1 d . . . . .
H30A H 0.302484 -0.434066 1.060835 0.041 Uiso 1 1 calc R U . . .
H30B H 0.214136 -0.388447 1.131822 0.041 Uiso 1 1 calc R U . . .
H30C H 0.388354 -0.306892 1.151221 0.041 Uiso 1 1 calc R U . . .
I2 I 0.25668(2) 0.34948(2) 0.42315(2) 0.01603(6) Uani 1 1 d . . . . .
N2 N 0.2572(3) 0.2590(3) 0.53768(17) 0.0151(6) Uani 1 1 d . . . . .
O2 O 0.2431(2) -0.1924(3) 0.88879(16) 0.0215(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 I1 2.6465(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.365(4) . ?
C1 N1 1.337(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C3 C4 1.407(4) . ?
C3 C6 1.469(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 N1 1.330(4) . ?
C6 C7 1.398(4) . ?
C6 C11 1.401(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 C10 1.395(4) . ?
C9 O1 1.357(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(4) . ?
C12 O1 1.443(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.512(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
I1 N1 2.303(3) . ?
Br2 I2 2.6716(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(4) . ?
C16 N2 1.333(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(4) . ?
C18 C19 1.404(4) . ?
C18 C21 1.472(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(4) . ?
C20 H20 0.9300 . ?
C20 N2 1.340(4) . ?
C21 C22 1.409(4) . ?
C21 C26 1.401(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(4) . ?
C24 C25 1.386(4) . ?
C24 O2 1.361(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.499(4) . ?
C27 O2 1.437(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.521(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.537(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
I2 N2 2.289(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(3) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 115.9(3) . . ?
C2 C3 C6 123.2(3) . . ?
C4 C3 C6 120.9(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 118.7 . . ?
N1 C5 C4 122.6(3) . . ?
N1 C5 H5 118.7 . . ?
C7 C6 C3 121.4(3) . . ?
C7 C6 C11 116.9(3) . . ?
C11 C6 C3 121.7(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.1(3) . . ?
O1 C9 C8 125.5(3) . . ?
O1 C9 C10 115.4(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.2 . . ?
C10 C11 C6 121.7(3) . . ?
C10 C11 H11 119.2 . . ?
H12A C12 H12B 108.6 . . ?
C13 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O1 C12 H12A 110.4 . . ?
O1 C12 H12B 110.4 . . ?
O1 C12 C13 106.4(3) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.8(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C13 C14 C15 110.3(3) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 I1 Br1 177.40(6) . . ?
C1 N1 I1 122.8(2) . . ?
C5 N1 C1 118.9(3) . . ?
C5 N1 I1 118.3(2) . . ?
C9 O1 C12 118.1(2) . . ?
C17 C16 H16 119.0 . . ?
N2 C16 H16 119.0 . . ?
N2 C16 C17 122.0(3) . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 115.8(3) . . ?
C17 C18 C21 123.2(3) . . ?
C19 C18 C21 121.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 118.8 . . ?
N2 C20 C19 122.5(3) . . ?
N2 C20 H20 118.8 . . ?
C22 C21 C18 121.0(3) . . ?
C26 C21 C18 122.5(3) . . ?
C26 C21 C22 116.5(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.5(3) . . ?
O2 C24 C23 115.3(3) . . ?
O2 C24 C25 125.2(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 H25 120.3 . . ?
C21 C26 H26 118.7 . . ?
C25 C26 C21 122.6(3) . . ?
C25 C26 H26 118.7 . . ?
H27A C27 H27B 108.4 . . ?
C28 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
O2 C27 H27A 110.0 . . ?
O2 C27 H27B 110.0 . . ?
O2 C27 C28 108.4(3) . . ?
C27 C28 H28A 108.5 . . ?
C27 C28 H28B 108.5 . . ?
C27 C28 C29 115.2(3) . . ?
H28A C28 H28B 107.5 . . ?
C29 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
C28 C29 C30 111.4(3) . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N2 I2 Br2 178.58(7) . . ?
C16 N2 C20 118.4(3) . . ?
C16 N2 I2 121.0(2) . . ?
C20 N2 I2 120.2(2) . . ?
C24 O2 C27 118.2(2) . . ?

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
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C2 C3 C6 179.5(3) . . . . ?
C2 C1 N1 C5 -0.9(5) . . . . ?
C2 C1 N1 I1 177.3(2) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C2 C3 C6 C7 -10.7(5) . . . . ?
C2 C3 C6 C11 169.5(3) . . . . ?
C3 C4 C5 N1 0.8(6) . . . . ?
C3 C6 C7 C8 -177.6(3) . . . . ?
C3 C6 C11 C10 177.3(3) . . . . ?
C4 C3 C6 C7 168.4(3) . . . . ?
C4 C3 C6 C11 -11.3(5) . . . . ?
C4 C5 N1 C1 0.1(5) . . . . ?
C4 C5 N1 I1 -178.1(3) . . . . ?
C6 C3 C4 C5 179.8(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C6 C11 C10 -2.4(5) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C7 C8 C9 O1 176.8(3) . . . . ?
C8 C9 C10 C11 1.9(5) . . . . ?
C8 C9 O1 C12 7.5(5) . . . . ?
C9 C10 C11 C6 0.4(5) . . . . ?
C10 C9 O1 C12 -173.5(3) . . . . ?
C11 C6 C7 C8 2.2(5) . . . . ?
C12 C13 C14 C15 -171.9(3) . . . . ?
C13 C12 O1 C9 -175.0(3) . . . . ?
N1 C1 C2 C3 0.7(5) . . . . ?
O1 C9 C10 C11 -177.2(3) . . . . ?
O1 C12 C13 C14 -173.1(3) . . . . ?
C16 C17 C18 C19 -2.5(5) . . . . ?
C16 C17 C18 C21 176.5(3) . . . . ?
C17 C16 N2 C20 0.8(5) . . . . ?
C17 C16 N2 I2 -172.3(3) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C17 C18 C21 C22 -14.6(5) . . . . ?
C17 C18 C21 C26 165.4(3) . . . . ?
C18 C19 C20 N2 0.6(5) . . . . ?
C18 C21 C22 C23 -179.5(3) . . . . ?
C18 C21 C26 C25 178.8(3) . . . . ?
C19 C18 C21 C22 164.3(3) . . . . ?
C19 C18 C21 C26 -15.6(5) . . . . ?
C19 C20 N2 C16 -1.7(5) . . . . ?
C19 C20 N2 I2 171.4(3) . . . . ?
C21 C18 C19 C20 -177.5(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C22 C21 C26 C25 -1.1(5) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C22 C23 C24 O2 178.4(3) . . . . ?
C23 C24 C25 C26 0.3(5) . . . . ?
C23 C24 O2 C27 177.4(3) . . . . ?
C24 C25 C26 C21 0.8(5) . . . . ?
C25 C24 O2 C27 -3.3(5) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
C27 C28 C29 C30 176.8(3) . . . . ?
C28 C27 O2 C24 175.5(3) . . . . ?
N2 C16 C17 C18 1.4(5) . . . . ?
O2 C24 C25 C26 -179.0(3) . . . . ?
O2 C27 C28 C29 59.9(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
1 -1 0 0.0535 1.0000 -1.0000 0.0000 0.0743 -0.0132 -0.0277
0 1 -2 0.0446 -0.0000 1.0000 -2.0000 -0.0043 -0.0525 0.0848
0 0 -1 0.0010 -0.0000 0.0000 -1.0000 0.0218 0.0013 0.0436
1 0 0 0.0365 0.9979 -0.0007 0.0038 0.0262 -0.0681 -0.0302
-1 -1 1 0.0418 -1.0000 -1.0000 1.0000 -0.0002 0.1221 -0.0111
0 0 1 0.0135 0.0000 -0.0000 1.0000 -0.0218 -0.0013 -0.0436
-2 1 1 0.0391 -1.9961 0.9985 0.9932 -0.1221 0.0801 0.0144

_olex2_date_sample_data_collection 1389983177.66
_olex2_date_sample_submission    1389225600
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_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_dwb1337
_database_code_depnum_ccdc_archive 'CCDC 2123972'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C15 H18 N O'
_chemical_formula_sum            'C15 H18 Br N O'
_chemical_formula_weight         308.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H18 Br1 N1 O1'
_chemical_oxdiff_usercomment     'Linda LJM380'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.6716(3)
_cell_length_b                   8.3651(4)
_cell_length_c                   13.0803(6)
_cell_angle_alpha                86.724(4)
_cell_angle_beta                 86.237(4)
_cell_angle_gamma                70.833(4)
_cell_volume                     687.56(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3054
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.3090
_cell_measurement_theta_min      3.1160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.977
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.2783
_exptl_crystal_size_mid          0.0772
_exptl_crystal_size_min          0.0314
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6296
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.030
_diffrn_reflns_theta_min         2.965
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    8.00   88.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   57.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   25.00   68.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802  -99.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   68.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802  -99.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   42.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802  -57.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega  -14.00   96.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4802   19.0000   60.0000 110
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0212039000
_diffrn_orient_matrix_UB_12      0.0557081000
_diffrn_orient_matrix_UB_13      0.0412072000
_diffrn_orient_matrix_UB_21      -0.0501638000
_diffrn_orient_matrix_UB_22      0.0691308000
_diffrn_orient_matrix_UB_23      -0.0336311000
_diffrn_orient_matrix_UB_31      -0.0986608000
_diffrn_orient_matrix_UB_32      -0.0136913000
_diffrn_orient_matrix_UB_33      0.0113305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3534
_reflns_number_total             4001
_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 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.063
_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)+(0.0273P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.08639(3) 0.29004(3) 0.91184(2) 0.02102(7) Uani 1 1 d . . . . .
C1 C -0.5738(4) 0.4822(3) 0.1416(2) 0.0289(5) Uani 1 1 d . . . . .
H1 H -0.673324 0.586721 0.156504 0.035 Uiso 1 1 calc R U . . .
C2 C -0.3798(3) 0.4328(3) 0.1837(2) 0.0272(5) Uani 1 1 d . . . . .
H2 H -0.348182 0.505290 0.226555 0.033 Uiso 1 1 calc R U . . .
C3 C -0.2285(3) 0.2766(3) 0.16380(17) 0.0182(4) Uani 1 1 d . . . . .
C4 C -0.2866(4) 0.1756(3) 0.0982(2) 0.0268(5) Uani 1 1 d . . . . .
H4 H -0.191662 0.069760 0.082188 0.032 Uiso 1 1 calc R U . . .
C5 C -0.4820(4) 0.2308(3) 0.0571(2) 0.0288(5) Uani 1 1 d . . . . .
H5 H -0.518145 0.162276 0.013100 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0210(3) 0.2196(3) 0.21050(17) 0.0176(4) Uani 1 1 d . . . . .
C7 C 0.0332(3) 0.3223(3) 0.27628(19) 0.0229(5) Uani 1 1 d . . . . .
H7 H -0.061315 0.430032 0.288319 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2229(3) 0.2684(3) 0.32386(19) 0.0242(5) Uani 1 1 d . . . . .
H8 H 0.254145 0.338827 0.368311 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3677(3) 0.1095(3) 0.30585(17) 0.0193(4) Uani 1 1 d . . . . .
C10 C 0.3202(3) 0.0067(3) 0.23857(19) 0.0245(5) Uani 1 1 d . . . . .
H10 H 0.417493 -0.099190 0.224455 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1274(3) 0.0623(3) 0.19247(19) 0.0245(5) Uani 1 1 d . . . . .
H11 H 0.096497 -0.008159 0.147910 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7002(3) -0.0972(3) 0.34491(19) 0.0231(5) Uani 1 1 d . . . . .
H12A H 0.748880 -0.111687 0.273452 0.028 Uiso 1 1 calc R U . . .
H12B H 0.636234 -0.183436 0.365749 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8837(3) -0.1137(3) 0.41002(19) 0.0217(4) Uani 1 1 d . . . . .
H13A H 0.832919 -0.095310 0.480976 0.026 Uiso 1 1 calc R U . . .
H13B H 0.948011 -0.028173 0.388010 0.026 Uiso 1 1 calc R U . . .
C14 C 1.0486(4) -0.2882(3) 0.4015(2) 0.0279(5) Uani 1 1 d . . . . .
H14A H 1.090630 -0.308859 0.329779 0.033 Uiso 1 1 calc R U . . .
H14B H 0.985166 -0.372517 0.427284 0.033 Uiso 1 1 calc R U . . .
C15 C 1.2449(4) -0.3091(3) 0.4602(2) 0.0363(6) Uani 1 1 d . . . . .
H15A H 1.308361 -0.225679 0.435303 0.054 Uiso 1 1 calc R U . . .
H15B H 1.345010 -0.420285 0.450554 0.054 Uiso 1 1 calc R U . . .
H15C H 1.205629 -0.294496 0.531826 0.054 Uiso 1 1 calc R U . . .
N1 N -0.6202(3) 0.3805(3) 0.07928(16) 0.0246(4) Uani 1 1 d . . . . .
H1A H -0.738(5) 0.409(4) 0.060(2) 0.038(8) Uiso 1 1 d . . . . .
O1 O 0.5477(2) 0.06825(19) 0.35801(13) 0.0222(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.366(3) . ?
C1 N1 1.330(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(3) . ?
C3 C4 1.394(3) . ?
C3 C6 1.470(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(3) . ?
C5 H5 0.9300 . ?
C5 N1 1.323(3) . ?
C6 C7 1.392(3) . ?
C6 C11 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 C10 1.384(3) . ?
C9 O1 1.355(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.502(3) . ?
C12 O1 1.435(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.517(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.517(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1A 0.79(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.1 . . ?
N1 C1 H1 120.1 . . ?
N1 C1 C2 119.9(2) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 115.97(19) . . ?
C2 C3 C6 122.2(2) . . ?
C4 C3 C6 121.8(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.6 . . ?
N1 C5 C4 120.8(2) . . ?
N1 C5 H5 119.6 . . ?
C7 C6 C3 120.85(19) . . ?
C11 C6 C3 122.1(2) . . ?
C11 C6 C7 117.08(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.28(19) . . ?
O1 C9 C8 115.30(19) . . ?
O1 C9 C10 125.42(19) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C6 C11 H11 118.9 . . ?
C10 C11 C6 122.1(2) . . ?
C10 C11 H11 118.9 . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O1 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
O1 C12 C13 107.97(18) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 C14 110.54(19) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.1(2) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 H1A 118(2) . . ?
C5 N1 C1 121.3(2) . . ?
C5 N1 H1A 121(2) . . ?
C9 O1 C12 117.66(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Br1 0.79(3) 2.72(3) 3.305(2) 132(3) 1_454 yes

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
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C6 -178.4(2) . . . . ?
C2 C1 N1 C5 0.3(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C6 C7 -0.8(3) . . . . ?
C2 C3 C6 C11 178.5(2) . . . . ?
C3 C4 C5 N1 -0.4(4) . . . . ?
C3 C6 C7 C8 177.3(2) . . . . ?
C3 C6 C11 C10 -178.2(2) . . . . ?
C4 C3 C6 C7 -179.7(2) . . . . ?
C4 C3 C6 C11 -0.4(3) . . . . ?
C4 C5 N1 C1 0.3(4) . . . . ?
C6 C3 C4 C5 179.0(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C6 C11 C10 1.1(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 O1 -179.0(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
C8 C9 O1 C12 177.9(2) . . . . ?
C9 C10 C11 C6 0.6(4) . . . . ?
C10 C9 O1 C12 -1.8(3) . . . . ?
C11 C6 C7 C8 -1.9(4) . . . . ?
C12 C13 C14 C15 176.3(2) . . . . ?
C13 C12 O1 C9 -179.71(19) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
O1 C9 C10 C11 178.1(2) . . . . ?
O1 C12 C13 C14 178.6(2) . . . . ?

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 0 -1 0.0187 0.0000 0.0000 -1.0000 -0.0412 0.0336 -0.0113
0 0 1 0.0127 -0.0000 -0.0000 1.0000 0.0412 -0.0336 0.0113
-1 0 0 0.1305 -1.0000 0.0000 0.0000 0.0212 0.0502 0.0987
1 0 0 0.1065 1.0000 -0.0000 -0.0000 -0.0212 -0.0502 -0.0987
0 1 0 0.0386 0.0000 1.0000 -0.0000 0.0557 0.0691 -0.0137
0 -1 0 0.0386 -0.0000 -1.0000 0.0000 -0.0557 -0.0691 0.0137
-1 -1 -2 0.1105 -1.0000 -1.0000 -2.0000 -0.1169 0.0483 0.0897

_olex2_date_sample_data_collection 1379001874.0
_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_dwb1330
_database_code_depnum_ccdc_archive 'CCDC 2123971'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br3, 2(C23 H33.465 N O)'
_chemical_formula_sum            'C46 H67 Br3 N2 O2'
_chemical_formula_weight         919.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C46 H67 Br3 N2 O2'
_chemical_oxdiff_usercomment     'James Jat33'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   28.1904(12)
_cell_length_b                   9.1296(2)
_cell_length_c                   17.0705(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.313(4)
_cell_angle_gamma                90
_cell_volume                     4347.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5037
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.0770
_cell_measurement_theta_min      3.2170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.822
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.2274
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15250
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.091
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         2.838
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   12.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9304  -99.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   87.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       16.3366   37.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   56.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       16.3366  -99.0000   90.0000 76
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0022988000
_diffrn_orient_matrix_UB_12      -0.0748572000
_diffrn_orient_matrix_UB_13      -0.0109140000
_diffrn_orient_matrix_UB_21      0.0253366000
_diffrn_orient_matrix_UB_22      -0.0063380000
_diffrn_orient_matrix_UB_23      0.0040613000
_diffrn_orient_matrix_UB_31      0.0006167000
_diffrn_orient_matrix_UB_32      -0.0197101000
_diffrn_orient_matrix_UB_33      0.0403166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5341
_reflns_number_total             7698
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         7698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+1.2128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          
;
The structure contained a disordered pair of pyridine and protonated
 pyridinium.  The pyridinium hydrogen was modelled in two
 places with occupancies of 0.53:0.47(4).  All hydrogens including N_H
 hydrogens were located using a riding model.
;
_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
2. Others
 Sof(H1A)=1-FVAR(1)
 Sof(H2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
  C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C31(H31), C33(H33),
 C34(H34), N2(H2), C1(H1), C2(H2A), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10),
 C11(H11), N1(H1A)
3.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.71943(2) 0.71702(4) 0.23550(2) 0.04138(13) Uani 1 1 d . . . . .
Br2 Br 0.75301(2) 0.75437(3) 0.10542(2) 0.03357(11) Uani 1 1 d . . . . .
Br3 Br 0.78419(2) 0.78674(4) -0.02567(2) 0.04751(14) Uani 1 1 d . . . . .
C24 C 0.28594(11) 0.5965(3) 1.00256(17) 0.0234(8) Uani 1 1 d . . . . .
H24 H 0.281753 0.502858 1.021838 0.028 Uiso 1 1 calc R U . . .
C25 C 0.30523(11) 0.6116(3) 0.93329(17) 0.0224(7) Uani 1 1 d . . . . .
H25 H 0.313308 0.528531 0.906579 0.027 Uiso 1 1 calc R U . . .
C26 C 0.31277(11) 0.7499(3) 0.90279(16) 0.0166(7) Uani 1 1 d . . . . .
C27 C 0.29854(11) 0.8681(3) 0.94595(17) 0.0214(7) Uani 1 1 d . . . . .
H27 H 0.302277 0.963299 0.928427 0.026 Uiso 1 1 calc R U . . .
C28 C 0.27904(11) 0.8444(3) 1.01418(17) 0.0229(8) Uani 1 1 d . . . . .
H28 H 0.269621 0.925109 1.041377 0.028 Uiso 1 1 calc R U . . .
C29 C 0.33359(10) 0.7713(3) 0.82884(16) 0.0153(7) Uani 1 1 d . . . . .
C30 C 0.35100(11) 0.6556(3) 0.78821(16) 0.0212(7) Uani 1 1 d . . . . .
H30 H 0.349006 0.561148 0.807839 0.025 Uiso 1 1 calc R U . . .
C31 C 0.37114(11) 0.6756(3) 0.71977(16) 0.0210(7) Uani 1 1 d . . . . .
H31 H 0.382352 0.595870 0.693893 0.025 Uiso 1 1 calc R U . . .
C32 C 0.37439(11) 0.8166(3) 0.69022(16) 0.0194(7) Uani 1 1 d . . . . .
C33 C 0.35629(11) 0.9328(3) 0.72801(17) 0.0236(8) Uani 1 1 d . . . . .
H33 H 0.357448 1.026646 0.707200 0.028 Uiso 1 1 calc R U . . .
C34 C 0.33651(11) 0.9114(3) 0.79622(17) 0.0221(7) Uani 1 1 d . . . . .
H34 H 0.324839 0.991490 0.821190 0.027 Uiso 1 1 calc R U . . .
C35 C 0.41368(11) 0.7355(3) 0.58033(17) 0.0204(7) Uani 1 1 d . . . . .
H35A H 0.388308 0.669189 0.558370 0.025 Uiso 1 1 calc R U . . .
H35B H 0.437910 0.680101 0.614116 0.025 Uiso 1 1 calc R U . . .
C36 C 0.43523(11) 0.8105(3) 0.51513(16) 0.0203(7) Uani 1 1 d . . . . .
H36A H 0.461355 0.872588 0.538782 0.024 Uiso 1 1 calc R U . . .
H36B H 0.411117 0.873160 0.485867 0.024 Uiso 1 1 calc R U . . .
C37 C 0.45414(11) 0.7057(3) 0.45725(16) 0.0196(7) Uani 1 1 d . . . . .
H37A H 0.477683 0.640696 0.486114 0.024 Uiso 1 1 calc R U . . .
H37B H 0.427947 0.646240 0.431335 0.024 Uiso 1 1 calc R U . . .
C38 C 0.47697(11) 0.7889(3) 0.39511(16) 0.0199(7) Uani 1 1 d . . . . .
H38A H 0.503679 0.845378 0.421721 0.024 Uiso 1 1 calc R U . . .
H38B H 0.453631 0.857544 0.368916 0.024 Uiso 1 1 calc R U . . .
C39 C 0.49505(11) 0.6937(3) 0.33217(16) 0.0206(7) Uani 1 1 d . . . . .
H39A H 0.518720 0.625318 0.357723 0.025 Uiso 1 1 calc R U . . .
H39B H 0.468523 0.637252 0.304871 0.025 Uiso 1 1 calc R U . . .
C40 C 0.51736(12) 0.7841(3) 0.27188(16) 0.0223(7) Uani 1 1 d . . . . .
H40A H 0.493314 0.850975 0.246003 0.027 Uiso 1 1 calc R U . . .
H40B H 0.543141 0.842584 0.299828 0.027 Uiso 1 1 calc R U . . .
C41 C 0.53713(11) 0.6945(3) 0.20872(17) 0.0238(8) Uani 1 1 d . . . . .
H41A H 0.511716 0.633692 0.181497 0.029 Uiso 1 1 calc R U . . .
H41B H 0.562118 0.630095 0.234096 0.029 Uiso 1 1 calc R U . . .
C42 C 0.55760(12) 0.7896(3) 0.14812(17) 0.0245(8) Uani 1 1 d . . . . .
H42A H 0.531972 0.849231 0.120590 0.029 Uiso 1 1 calc R U . . .
H42B H 0.581275 0.855343 0.176044 0.029 Uiso 1 1 calc R U . . .
C43 C 0.58063(12) 0.7049(3) 0.08759(17) 0.0240(8) Uani 1 1 d . . . . .
H43A H 0.557402 0.636248 0.061038 0.029 Uiso 1 1 calc R U . . .
H43B H 0.607202 0.648517 0.114813 0.029 Uiso 1 1 calc R U . . .
C44 C 0.59899(11) 0.8012(3) 0.02562(17) 0.0235(8) Uani 1 1 d . . . . .
H44A H 0.572150 0.854791 -0.002756 0.028 Uiso 1 1 calc R U . . .
H44B H 0.621216 0.872270 0.052464 0.028 Uiso 1 1 calc R U . . .
C45 C 0.62369(12) 0.7193(3) -0.03344(18) 0.0286(8) Uani 1 1 d . . . . .
H45A H 0.602000 0.645265 -0.058775 0.034 Uiso 1 1 calc R U . . .
H45B H 0.651446 0.669296 -0.005440 0.034 Uiso 1 1 calc R U . . .
C46 C 0.63984(12) 0.8164(4) -0.09702(18) 0.0323(9) Uani 1 1 d . . . . .
H46A H 0.660315 0.892506 -0.072467 0.048 Uiso 1 1 calc R U . . .
H46B H 0.612307 0.859406 -0.128274 0.048 Uiso 1 1 calc R U . . .
H46C H 0.657106 0.758559 -0.130455 0.048 Uiso 1 1 calc R U . . .
N2 N 0.27299(9) 0.7117(3) 1.04314(14) 0.0202(6) Uani 1 1 d . . . . .
H2 H 0.261176 0.700266 1.086439 0.024 Uiso 0.47(4) 1 calc R U P A 1
O2 O 0.39488(7) 0.8507(2) 0.62437(11) 0.0249(5) Uani 1 1 d . . . . .
C1 C 0.78036(11) 0.4041(3) 0.78657(17) 0.0245(8) Uani 1 1 d . . . . .
H1 H 0.777533 0.496727 0.808049 0.029 Uiso 1 1 calc R U . . .
C2 C 0.79928(11) 0.3914(3) 0.71683(17) 0.0247(8) Uani 1 1 d . . . . .
H2A H 0.808791 0.475131 0.692288 0.030 Uiso 1 1 calc R U . . .
C3 C 0.80438(11) 0.2543(3) 0.68242(17) 0.0189(7) Uani 1 1 d . . . . .
C4 C 0.78852(11) 0.1353(3) 0.72350(17) 0.0243(8) Uani 1 1 d . . . . .
H4 H 0.790829 0.040996 0.703772 0.029 Uiso 1 1 calc R U . . .
C5 C 0.76963(11) 0.1557(4) 0.79236(17) 0.0243(8) Uani 1 1 d . . . . .
H5 H 0.758989 0.074421 0.817674 0.029 Uiso 1 1 calc R U . . .
C6 C 0.82514(11) 0.2353(3) 0.60842(17) 0.0187(7) Uani 1 1 d . . . . .
C7 C 0.84046(11) 0.3536(3) 0.56672(17) 0.0230(8) Uani 1 1 d . . . . .
H7 H 0.837014 0.447953 0.585603 0.028 Uiso 1 1 calc R U . . .
C8 C 0.86064(11) 0.3348(3) 0.49811(17) 0.0248(8) Uani 1 1 d . . . . .
H8 H 0.870544 0.415435 0.471410 0.030 Uiso 1 1 calc R U . . .
C9 C 0.86590(11) 0.1947(3) 0.46971(17) 0.0221(7) Uani 1 1 d . . . . .
C10 C 0.84952(11) 0.0753(3) 0.50824(17) 0.0247(8) Uani 1 1 d . . . . .
H10 H 0.851829 -0.018513 0.487885 0.030 Uiso 1 1 calc R U . . .
C11 C 0.82981(11) 0.0958(3) 0.57679(17) 0.0238(8) Uani 1 1 d . . . . .
H11 H 0.819377 0.014818 0.602591 0.029 Uiso 1 1 calc R U . . .
C12 C 0.90589(12) 0.2714(3) 0.35907(17) 0.0231(8) Uani 1 1 d . . . . .
H12A H 0.930624 0.325821 0.392357 0.028 Uiso 1 1 calc R U . . .
H12B H 0.881033 0.339096 0.336699 0.028 Uiso 1 1 calc R U . . .
C13 C 0.92666(11) 0.1919(3) 0.29437(17) 0.0214(7) Uani 1 1 d . . . . .
H13A H 0.901666 0.132405 0.264958 0.026 Uiso 1 1 calc R U . . .
H13B H 0.951566 0.126124 0.318652 0.026 Uiso 1 1 calc R U . . .
C14 C 0.94767(11) 0.2906(3) 0.23663(17) 0.0214(7) Uani 1 1 d . . . . .
H14A H 0.972942 0.349923 0.265395 0.026 Uiso 1 1 calc R U . . .
H14B H 0.922935 0.356088 0.211527 0.026 Uiso 1 1 calc R U . . .
C15 C 0.96793(11) 0.2029(3) 0.17326(17) 0.0219(7) Uani 1 1 d . . . . .
H15A H 0.942579 0.142540 0.145544 0.026 Uiso 1 1 calc R U . . .
H15B H 0.992633 0.137909 0.198897 0.026 Uiso 1 1 calc R U . . .
C16 C 0.98915(12) 0.2958(3) 0.11280(17) 0.0241(8) Uani 1 1 d . . . . .
H16A H 0.964209 0.358334 0.085598 0.029 Uiso 1 1 calc R U . . .
H16B H 1.013815 0.358688 0.140478 0.029 Uiso 1 1 calc R U . . .
C17 C 1.01075(12) 0.2058(3) 0.05169(17) 0.0238(8) Uani 1 1 d . . . . .
H17A H 0.986471 0.139977 0.025478 0.029 Uiso 1 1 calc R U . . .
H17B H 1.036648 0.146432 0.078619 0.029 Uiso 1 1 calc R U . . .
C18 C 1.02999(12) 0.2997(3) -0.01057(17) 0.0247(8) Uani 1 1 d . . . . .
H18A H 1.003557 0.353429 -0.040051 0.030 Uiso 1 1 calc R U . . .
H18B H 1.052351 0.370687 0.016038 0.030 Uiso 1 1 calc R U . . .
C19 C 1.05510(12) 0.2125(3) -0.06852(18) 0.0276(8) Uani 1 1 d . . . . .
H19A H 1.083295 0.165999 -0.039706 0.033 Uiso 1 1 calc R U . . .
H19B H 1.033768 0.135737 -0.091671 0.033 Uiso 1 1 calc R U . . .
C20 C 1.07014(11) 0.3049(3) -0.13438(17) 0.0233(7) Uani 1 1 d . . . . .
H20A H 1.090128 0.384317 -0.110724 0.028 Uiso 1 1 calc R U . . .
H20B H 1.041646 0.348183 -0.164068 0.028 Uiso 1 1 calc R U . . .
C21 C 1.09722(12) 0.2244(4) -0.19191(18) 0.0299(8) Uani 1 1 d . . . . .
H21A H 1.126445 0.184047 -0.162945 0.036 Uiso 1 1 calc R U . . .
H21B H 1.077780 0.143149 -0.214824 0.036 Uiso 1 1 calc R U . . .
C22 C 1.11003(12) 0.3206(4) -0.25817(17) 0.0270(8) Uani 1 1 d . . . . .
H22A H 1.080822 0.362558 -0.286273 0.032 Uiso 1 1 calc R U . . .
H22B H 1.129959 0.400678 -0.235150 0.032 Uiso 1 1 calc R U . . .
C23 C 1.13615(14) 0.2412(4) -0.3170(2) 0.0455(11) Uani 1 1 d . . . . .
H23A H 1.166619 0.207422 -0.290757 0.068 Uiso 1 1 calc R U . . .
H23B H 1.141034 0.306784 -0.359010 0.068 Uiso 1 1 calc R U . . .
H23C H 1.117379 0.158961 -0.338403 0.068 Uiso 1 1 calc R U . . .
N1 N 0.76593(9) 0.2877(3) 0.82439(14) 0.0214(6) Uani 1 1 d . . . . .
H1A H 0.754575 0.297632 0.868212 0.026 Uiso 0.53(4) 1 calc R U P A 2
O1 O 0.88625(8) 0.1588(2) 0.40396(11) 0.0267(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Br2 2.5595(5) . ?
Br2 Br3 2.5369(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C24 N2 1.339(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.394(4) . ?
C26 C27 1.398(4) . ?
C26 C29 1.480(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(4) . ?
C28 H28 0.9300 . ?
C28 N2 1.328(4) . ?
C29 C30 1.391(4) . ?
C29 C34 1.403(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.383(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.391(4) . ?
C32 C33 1.377(4) . ?
C32 O2 1.372(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.376(4) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.507(4) . ?
C35 O2 1.438(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.526(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.521(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.526(4) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.524(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.522(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.526(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.511(4) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.523(4) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C45 1.504(4) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 C46 1.522(4) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
N2 H2 0.8600 . ?
C1 H1 0.9300 . ?
C1 C2 1.378(4) . ?
C1 N1 1.337(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.398(4) . ?
C3 C4 1.401(4) . ?
C3 C6 1.477(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 N1 1.333(4) . ?
C6 C7 1.396(4) . ?
C6 C11 1.397(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(4) . ?
C9 C10 1.387(4) . ?
C9 O1 1.372(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.509(4) . ?
C12 O1 1.440(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.518(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.522(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.523(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.523(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.525(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.522(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.514(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.518(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.517(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.513(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 H1A 0.8600 . ?

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
Br3 Br2 Br1 178.24(2) . . ?
C25 C24 H24 118.8 . . ?
N2 C24 H24 118.8 . . ?
N2 C24 C25 122.4(3) . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C27 115.6(3) . . ?
C25 C26 C29 122.6(3) . . ?
C27 C26 C29 121.8(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 118.4 . . ?
N2 C28 C27 123.2(3) . . ?
N2 C28 H28 118.4 . . ?
C30 C29 C26 122.5(3) . . ?
C30 C29 C34 116.7(3) . . ?
C34 C29 C26 120.8(3) . . ?
C29 C30 H30 118.7 . . ?
C31 C30 C29 122.6(3) . . ?
C31 C30 H30 118.7 . . ?
C30 C31 H31 120.5 . . ?
C30 C31 C32 119.0(3) . . ?
C32 C31 H31 120.5 . . ?
C33 C32 C31 119.7(3) . . ?
O2 C32 C31 124.4(3) . . ?
O2 C32 C33 116.0(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H33 119.7 . . ?
C29 C34 H34 119.3 . . ?
C33 C34 C29 121.3(3) . . ?
C33 C34 H34 119.3 . . ?
H35A C35 H35B 108.7 . . ?
C36 C35 H35A 110.6 . . ?
C36 C35 H35B 110.6 . . ?
O2 C35 H35A 110.6 . . ?
O2 C35 H35B 110.6 . . ?
O2 C35 C36 105.8(2) . . ?
C35 C36 H36A 108.7 . . ?
C35 C36 H36B 108.7 . . ?
C35 C36 C37 114.1(2) . . ?
H36A C36 H36B 107.6 . . ?
C37 C36 H36A 108.7 . . ?
C37 C36 H36B 108.7 . . ?
C36 C37 H37A 109.4 . . ?
C36 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C38 C37 C36 111.2(2) . . ?
C38 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
C37 C38 H38A 108.5 . . ?
C37 C38 H38B 108.5 . . ?
C37 C38 C39 115.2(2) . . ?
H38A C38 H38B 107.5 . . ?
C39 C38 H38A 108.5 . . ?
C39 C38 H38B 108.5 . . ?
C38 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
H39A C39 H39B 107.9 . . ?
C40 C39 C38 112.3(2) . . ?
C40 C39 H39A 109.1 . . ?
C40 C39 H39B 109.1 . . ?
C39 C40 H40A 108.6 . . ?
C39 C40 H40B 108.6 . . ?
H40A C40 H40B 107.6 . . ?
C41 C40 C39 114.6(3) . . ?
C41 C40 H40A 108.6 . . ?
C41 C40 H40B 108.6 . . ?
C40 C41 H41A 109.0 . . ?
C40 C41 H41B 109.0 . . ?
C40 C41 C42 112.8(3) . . ?
H41A C41 H41B 107.8 . . ?
C42 C41 H41A 109.0 . . ?
C42 C41 H41B 109.0 . . ?
C41 C42 H42A 108.6 . . ?
C41 C42 H42B 108.6 . . ?
H42A C42 H42B 107.6 . . ?
C43 C42 C41 114.5(3) . . ?
C43 C42 H42A 108.6 . . ?
C43 C42 H42B 108.6 . . ?
C42 C43 H43A 108.8 . . ?
C42 C43 H43B 108.8 . . ?
C42 C43 C44 113.7(3) . . ?
H43A C43 H43B 107.7 . . ?
C44 C43 H43A 108.8 . . ?
C44 C43 H43B 108.8 . . ?
C43 C44 H44A 108.6 . . ?
C43 C44 H44B 108.6 . . ?
H44A C44 H44B 107.6 . . ?
C45 C44 C43 114.5(3) . . ?
C45 C44 H44A 108.6 . . ?
C45 C44 H44B 108.6 . . ?
C44 C45 H45A 108.8 . . ?
C44 C45 H45B 108.8 . . ?
C44 C45 C46 113.8(3) . . ?
H45A C45 H45B 107.7 . . ?
C46 C45 H45A 108.8 . . ?
C46 C45 H45B 108.8 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C24 N2 H2 121.2 . . ?
C28 N2 C24 117.7(3) . . ?
C28 N2 H2 121.2 . . ?
C32 O2 C35 119.5(2) . . ?
C2 C1 H1 118.9 . . ?
N1 C1 H1 118.9 . . ?
N1 C1 C2 122.2(3) . . ?
C1 C2 H2A 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 115.1(3) . . ?
C2 C3 C6 122.8(3) . . ?
C4 C3 C6 122.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 118.7 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 H5 118.7 . . ?
C7 C6 C3 122.4(3) . . ?
C7 C6 C11 117.0(3) . . ?
C11 C6 C3 120.6(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.1(3) . . ?
O1 C9 C8 125.9(3) . . ?
O1 C9 C10 114.0(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.2 . . ?
C10 C11 C6 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
O1 C12 H12A 110.7 . . ?
O1 C12 H12B 110.7 . . ?
O1 C12 C13 105.4(2) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.7(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C13 C14 C15 111.8(2) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C14 C15 C16 114.4(2) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.5(2) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C16 C17 C18 113.1(3) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.9(3) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.5(3) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
C19 C20 C21 115.6(3) . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.5(3) . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C21 114.1(3) . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 H1A 120.9 . . ?
C5 N1 C1 118.2(3) . . ?
C5 N1 H1A 120.9 . . ?
C9 O1 C12 120.2(2) . . ?

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
C24 C25 C26 C27 -1.4(5) . . . . ?
C24 C25 C26 C29 179.7(3) . . . . ?
C25 C24 N2 C28 0.4(5) . . . . ?
C25 C26 C27 C28 0.7(4) . . . . ?
C25 C26 C29 C30 -5.8(5) . . . . ?
C25 C26 C29 C34 174.0(3) . . . . ?
C26 C27 C28 N2 0.6(5) . . . . ?
C26 C29 C30 C31 -179.0(3) . . . . ?
C26 C29 C34 C33 179.2(3) . . . . ?
C27 C26 C29 C30 175.4(3) . . . . ?
C27 C26 C29 C34 -4.8(4) . . . . ?
C27 C28 N2 C24 -1.2(4) . . . . ?
C29 C26 C27 C28 179.6(3) . . . . ?
C29 C30 C31 C32 0.2(5) . . . . ?
C30 C29 C34 C33 -0.9(5) . . . . ?
C30 C31 C32 C33 -2.0(5) . . . . ?
C30 C31 C32 O2 178.0(3) . . . . ?
C31 C32 C33 C34 2.3(5) . . . . ?
C31 C32 O2 C35 1.5(4) . . . . ?
C32 C33 C34 C29 -0.8(5) . . . . ?
C33 C32 O2 C35 -178.6(3) . . . . ?
C34 C29 C30 C31 1.2(5) . . . . ?
C35 C36 C37 C38 -177.9(3) . . . . ?
C36 C35 O2 C32 -177.5(2) . . . . ?
C36 C37 C38 C39 -177.4(3) . . . . ?
C37 C38 C39 C40 179.9(3) . . . . ?
C38 C39 C40 C41 178.6(3) . . . . ?
C39 C40 C41 C42 178.1(3) . . . . ?
C40 C41 C42 C43 176.1(3) . . . . ?
C41 C42 C43 C44 177.6(3) . . . . ?
C42 C43 C44 C45 177.9(3) . . . . ?
C43 C44 C45 C46 177.5(3) . . . . ?
N2 C24 C25 C26 0.9(5) . . . . ?
O2 C32 C33 C34 -177.7(3) . . . . ?
O2 C35 C36 C37 -175.7(2) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C6 -179.0(3) . . . . ?
C2 C1 N1 C5 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C6 C7 -1.1(5) . . . . ?
C2 C3 C6 C11 179.5(3) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C3 C6 C7 C8 178.9(3) . . . . ?
C3 C6 C11 C10 -179.3(3) . . . . ?
C4 C3 C6 C7 179.2(3) . . . . ?
C4 C3 C6 C11 -0.2(5) . . . . ?
C4 C5 N1 C1 1.5(4) . . . . ?
C6 C3 C4 C5 179.6(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C6 C11 C10 1.2(5) . . . . ?
C7 C8 C9 C10 2.3(5) . . . . ?
C7 C8 C9 O1 -178.2(3) . . . . ?
C8 C9 C10 C11 -2.7(5) . . . . ?
C8 C9 O1 C12 2.0(5) . . . . ?
C9 C10 C11 C6 0.9(5) . . . . ?
C10 C9 O1 C12 -178.5(3) . . . . ?
C11 C6 C7 C8 -1.7(5) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C13 C12 O1 C9 177.7(3) . . . . ?
C13 C14 C15 C16 179.4(3) . . . . ?
C14 C15 C16 C17 178.0(3) . . . . ?
C15 C16 C17 C18 177.6(3) . . . . ?
C16 C17 C18 C19 175.6(3) . . . . ?
C17 C18 C19 C20 174.8(3) . . . . ?
C18 C19 C20 C21 177.5(3) . . . . ?
C19 C20 C21 C22 178.1(3) . . . . ?
C20 C21 C22 C23 -178.8(3) . . . . ?
N1 C1 C2 C3 -0.2(5) . . . . ?
O1 C9 C10 C11 177.7(3) . . . . ?
O1 C12 C13 C14 177.4(2) . . . . ?

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
-1 0 0 0.0230 -0.9981 0.0003 -0.0004 0.0023 -0.0253 -0.0006
-2 0 -1 0.0663 -1.9942 0.0002 -0.9995 0.0155 -0.0546 -0.0415
4 0 -1 0.0381 3.9940 -0.0015 -0.9970 0.0018 0.0972 -0.0377
0 1 1 0.0891 -0.0019 0.9990 0.9990 -0.0857 -0.0023 0.0206
0 2 -3 0.0459 0.0054 1.9963 -2.9953 -0.1168 -0.0247 -0.1601
0 -2 -1 0.1000 0.0020 -1.9976 -0.9993 0.1604 0.0087 -0.0009
0 0 1 0.0705 -0.0018 0.0003 0.9986 -0.0109 0.0040 0.0403
1 0 0 0.0230 0.9981 -0.0003 0.0004 -0.0023 0.0253 0.0006
0 -2 3 0.1111 -0.0054 -1.9963 2.9953 0.1168 0.0247 0.1601

_olex2_date_sample_data_collection 1369138142.16
_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_dwb1332
_database_code_depnum_ccdc_archive 'CCDC 2123974'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-24 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.11.04 svn.r5db059d7 for OlexSys, GUI svn.r6419)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C23 H34 N O'
_chemical_formula_sum            'C23 H34 Br N O'
_chemical_formula_weight         420.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H33 Br2 N1 O1'
_chemical_oxdiff_usercomment     'Linda LJM365a'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7504(3)
_cell_length_b                   8.3652(4)
_cell_length_c                   20.1363(10)
_cell_angle_alpha                81.710(4)
_cell_angle_beta                 86.632(4)
_cell_angle_gamma                70.675(4)
_cell_volume                     1061.71(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4126
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      29.0120
_cell_measurement_theta_min      3.3650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_recrystallization_method THF
_exptl_crystal_size_max          0.2183
_exptl_crystal_size_mid          0.0703
_exptl_crystal_size_min          0.0616
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7571
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.324
_diffrn_reflns_theta_min         2.920
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   50.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.3323   57.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   -5.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.3323  -57.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00    9.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.3323  -77.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -42.00   46.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7386  -77.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   -6.00   89.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7386   77.0000  120.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0229551000
_diffrn_orient_matrix_UB_12      0.0403474000
_diffrn_orient_matrix_UB_13      0.0294976000
_diffrn_orient_matrix_UB_21      0.1079223000
_diffrn_orient_matrix_UB_22      -0.0323236000
_diffrn_orient_matrix_UB_23      0.0083602000
_diffrn_orient_matrix_UB_31      0.0150342000
_diffrn_orient_matrix_UB_32      0.0744662000
_diffrn_orient_matrix_UB_33      -0.0180919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4301
_reflns_number_total             4902
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4902
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.1746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -1.41940(3) 1.26226(3) 1.06064(2) 0.01863(7) Uani 1 1 d . . . . .
C1 C -1.0602(3) 1.5165(3) 0.90983(11) 0.0243(5) Uani 1 1 d . . . . .
H1 H -1.162719 1.625947 0.899645 0.029 Uiso 1 1 calc R U . . .
C2 C -0.8636(3) 1.4840(3) 0.88201(11) 0.0221(5) Uani 1 1 d . . . . .
H2 H -0.830531 1.572116 0.853106 0.026 Uiso 1 1 calc R U . . .
C3 C -0.7096(3) 1.3229(3) 0.89529(10) 0.0160(4) Uani 1 1 d . . . . .
C4 C -0.7687(3) 1.2004(3) 0.93938(11) 0.0227(5) Uani 1 1 d . . . . .
H4 H -0.670192 1.089580 0.950734 0.027 Uiso 1 1 calc R U . . .
C5 C -0.9674(4) 1.2395(3) 0.96621(12) 0.0248(5) Uani 1 1 d . . . . .
H5 H -1.005472 1.154984 0.995861 0.030 Uiso 1 1 calc R U . . .
C6 C -0.4991(3) 1.2843(3) 0.86403(10) 0.0155(4) Uani 1 1 d . . . . .
C7 C -0.4429(3) 1.4100(3) 0.82130(10) 0.0186(5) Uani 1 1 d . . . . .
H7 H -0.539945 1.522782 0.814120 0.022 Uiso 1 1 calc R U . . .
C8 C -0.2508(3) 1.3743(3) 0.78954(11) 0.0201(5) Uani 1 1 d . . . . .
H8 H -0.217655 1.461891 0.760254 0.024 Uiso 1 1 calc R U . . .
C9 C -0.1036(3) 1.2108(3) 0.79980(10) 0.0160(4) Uani 1 1 d . . . . .
C10 C -0.1526(3) 1.0833(3) 0.84330(10) 0.0185(5) Uani 1 1 d . . . . .
H10 H -0.053014 0.971860 0.851621 0.022 Uiso 1 1 calc R U . . .
C11 C -0.3492(3) 1.1216(3) 0.87432(10) 0.0185(5) Uani 1 1 d . . . . .
H11 H -0.382711 1.034096 0.903525 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2405(3) 1.0266(3) 0.77328(11) 0.0192(5) Uani 1 1 d . . . . .
H12A H 0.186782 0.938260 0.760964 0.023 Uiso 1 1 calc R U . . .
H12B H 0.286332 0.994765 0.820561 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4216(3) 1.0405(3) 0.72773(11) 0.0195(5) Uani 1 1 d . . . . .
H13A H 0.473664 1.128830 0.740917 0.023 Uiso 1 1 calc R U . . .
H13B H 0.371451 1.077322 0.680991 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6018(3) 0.8713(3) 0.73077(11) 0.0196(5) Uani 1 1 d . . . . .
H14A H 0.651561 0.834716 0.777559 0.024 Uiso 1 1 calc R U . . .
H14B H 0.549091 0.783025 0.717798 0.024 Uiso 1 1 calc R U . . .
C15 C 0.7855(3) 0.8827(3) 0.68503(11) 0.0203(5) Uani 1 1 d . . . . .
H15A H 0.840957 0.968310 0.699059 0.024 Uiso 1 1 calc R U . . .
H15B H 0.734311 0.923539 0.638542 0.024 Uiso 1 1 calc R U . . .
C16 C 0.9635(3) 0.7134(3) 0.68566(11) 0.0201(5) Uani 1 1 d . . . . .
H16A H 1.012565 0.672411 0.732364 0.024 Uiso 1 1 calc R U . . .
H16B H 0.907300 0.628564 0.671427 0.024 Uiso 1 1 calc R U . . .
C17 C 1.1510(3) 0.7198(3) 0.64111(11) 0.0202(5) Uani 1 1 d . . . . .
H17A H 1.213056 0.799840 0.656502 0.024 Uiso 1 1 calc R U . . .
H17B H 1.102774 0.764491 0.594512 0.024 Uiso 1 1 calc R U . . .
C18 C 1.3191(3) 0.5448(3) 0.64177(11) 0.0213(5) Uani 1 1 d . . . . .
H18A H 1.362679 0.499287 0.688719 0.026 Uiso 1 1 calc R U . . .
H18B H 1.256531 0.466307 0.625460 0.026 Uiso 1 1 calc R U . . .
C19 C 1.5128(3) 0.5444(3) 0.59960(11) 0.0211(5) Uani 1 1 d . . . . .
H19A H 1.578980 0.619797 0.616508 0.025 Uiso 1 1 calc R U . . .
H19B H 1.470363 0.591395 0.552657 0.025 Uiso 1 1 calc R U . . .
C20 C 1.6725(3) 0.3662(3) 0.60088(11) 0.0221(5) Uani 1 1 d . . . . .
H20A H 1.710084 0.318925 0.648145 0.027 Uiso 1 1 calc R U . . .
H20B H 1.605217 0.292345 0.583358 0.027 Uiso 1 1 calc R U . . .
C21 C 1.8730(3) 0.3563(3) 0.56096(11) 0.0221(5) Uani 1 1 d . . . . .
H21A H 1.944081 0.426719 0.579065 0.027 Uiso 1 1 calc R U . . .
H21B H 1.837112 0.404505 0.513667 0.027 Uiso 1 1 calc R U . . .
C22 C 2.0227(3) 0.1742(3) 0.56332(12) 0.0256(5) Uani 1 1 d . . . . .
H22A H 2.053476 0.125411 0.610842 0.031 Uiso 1 1 calc R U . . .
H22B H 1.951661 0.105279 0.544189 0.031 Uiso 1 1 calc R U . . .
C23 C 2.2290(4) 0.1577(3) 0.52580(13) 0.0307(6) Uani 1 1 d . . . . .
H23A H 2.304462 0.220563 0.545781 0.046 Uiso 1 1 calc R U . . .
H23B H 2.200821 0.204984 0.478561 0.046 Uiso 1 1 calc R U . . .
H23C H 2.314862 0.036805 0.528844 0.046 Uiso 1 1 calc R U . . .
N1 N -1.1088(3) 1.3948(3) 0.95129(9) 0.0214(4) Uani 1 1 d . . . . .
H1A H -1.235(4) 1.415(4) 0.9673(13) 0.036(8) Uiso 1 1 d . . . . .
O1 O 0.0795(2) 1.1912(2) 0.76500(7) 0.0213(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.366(3) . ?
C1 N1 1.336(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(3) . ?
C3 C4 1.401(3) . ?
C3 C6 1.473(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9500 . ?
C5 N1 1.338(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(3) . ?
C9 C10 1.394(3) . ?
C9 O1 1.357(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.510(3) . ?
C12 O1 1.438(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.519(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.526(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.516(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.519(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.519(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1A 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.9 . . ?
N1 C1 H1 119.9 . . ?
N1 C1 C2 120.2(2) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C6 121.92(19) . . ?
C4 C3 C2 116.1(2) . . ?
C4 C3 C6 122.0(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.5 . . ?
N1 C5 C4 121.0(2) . . ?
N1 C5 H5 119.5 . . ?
C7 C6 C3 120.8(2) . . ?
C11 C6 C3 122.08(19) . . ?
C11 C6 C7 117.14(19) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.34(19) . . ?
O1 C9 C8 115.04(19) . . ?
O1 C9 C10 125.6(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.5 . . ?
C6 C11 H11 118.9 . . ?
C10 C11 C6 122.2(2) . . ?
C10 C11 H11 118.9 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
O1 C12 H12A 110.3 . . ?
O1 C12 H12B 110.3 . . ?
O1 C12 C13 107.12(17) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.13(18) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.85(18) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C14 C15 C16 113.49(19) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 115.12(19) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.42(19) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.71(19) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.38(19) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 C19 115.4(2) . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C20 C21 C22 112.4(2) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C21 114.5(2) . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C5 121.0(2) . . ?
C1 N1 H1A 119.5(18) . . ?
C5 N1 H1A 119.4(18) . . ?
C9 O1 C12 118.52(16) . . ?

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
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C6 178.1(2) . . . . ?
C2 C1 N1 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C6 C7 2.2(3) . . . . ?
C2 C3 C6 C11 -176.5(2) . . . . ?
C3 C4 C5 N1 -0.3(4) . . . . ?
C3 C6 C7 C8 -177.18(19) . . . . ?
C3 C6 C11 C10 178.01(19) . . . . ?
C4 C3 C6 C7 -178.6(2) . . . . ?
C4 C3 C6 C11 2.7(3) . . . . ?
C4 C5 N1 C1 -0.1(3) . . . . ?
C6 C3 C4 C5 -178.3(2) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 O1 179.32(19) . . . . ?
C8 C9 C10 C11 1.4(3) . . . . ?
C8 C9 O1 C12 179.42(19) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C10 C9 O1 C12 -0.7(3) . . . . ?
C11 C6 C7 C8 1.6(3) . . . . ?
C12 C13 C14 C15 179.86(18) . . . . ?
C13 C12 O1 C9 178.44(17) . . . . ?
C13 C14 C15 C16 -178.01(19) . . . . ?
C14 C15 C16 C17 -179.45(18) . . . . ?
C15 C16 C17 C18 -177.54(19) . . . . ?
C16 C17 C18 C19 -178.42(18) . . . . ?
C17 C18 C19 C20 -178.69(19) . . . . ?
C18 C19 C20 C21 -178.69(18) . . . . ?
C19 C20 C21 C22 -178.7(2) . . . . ?
C20 C21 C22 C23 -178.28(19) . . . . ?
N1 C1 C2 C3 0.9(4) . . . . ?
O1 C9 C10 C11 -178.48(19) . . . . ?
O1 C12 C13 C14 -178.61(17) . . . . ?

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 -1 2 0.0315 0.0000 -1.0000 2.0000 0.0186 0.0490 -0.1106
0 1 -2 0.0315 -0.0000 1.0000 -2.0000 -0.0186 -0.0490 0.1106
-1 -1 0 0.0863 -1.0000 -1.0000 0.0000 -0.0174 -0.0756 -0.0895
0 -1 -1 0.0318 0.0000 -1.0000 -1.0000 -0.0698 0.0240 -0.0564
0 1 1 0.0318 -0.0000 1.0000 1.0000 0.0698 -0.0240 0.0564
-1 -1 4 0.0469 -1.0000 -1.0000 4.0000 0.1006 -0.0422 -0.1619
1 1 -4 0.0469 1.0000 1.0000 -4.0000 -0.1006 0.0422 0.1619
-1 1 2 0.0527 -1.0000 1.0000 2.0000 0.1223 -0.1235 0.0232
0 1 7 0.0235 -0.0000 1.0000 7.0000 0.2468 0.0262 -0.0522
0 -1 -5 0.0378 0.0000 -1.0000 -5.0000 -0.1878 -0.0095 0.0160
0 0 1 0.0174 -0.0000 -0.0000 1.0000 0.0295 0.0084 -0.0181
1 2 6 0.0313 1.0000 2.0000 6.0000 0.2347 0.0934 0.0554

_olex2_date_sample_data_collection 1373388768.49
_olex2_date_sample_submission    08/07/2013
_olex2_exptl_crystal_mounting_method 'oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'

###end
