# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1566473'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          316
_chemical_formula_moiety         'C20 H32 Br N O'
_chemical_formula_sum            'C20 H32 Br N O'
_chemical_formula_weight         382.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.834(9)
_cell_length_b                   5.686(5)
_cell_length_c                   35.79(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.958(11)
_cell_angle_gamma                90
_cell_volume                     1996(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3555
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.064
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            19457
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         3.190
_diffrn_reflns_theta_max         27.423
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4538
_reflns_number_gt                3655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+2.6811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1314(2) 1.4097(4) 0.32534(7) 0.0275(6) Uani 1 1 d . . . . .
H1 H 0.085(4) 1.340(7) 0.3324(11) 0.041 Uiso 1 1 d . U . . .
C1 C 0.1758(3) 1.2889(6) 0.29634(8) 0.0198(6) Uani 1 1 d . . . . .
C2 C 0.2811(3) 1.3850(6) 0.27673(8) 0.0238(7) Uani 1 1 d . . . . .
H2 H 0.318876 1.533198 0.284024 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3308(3) 1.2647(6) 0.24659(8) 0.0228(7) Uani 1 1 d . . . . .
H3 H 0.402508 1.330367 0.233481 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2746(3) 1.0459(6) 0.23563(8) 0.0214(7) Uani 1 1 d . . . . .
C5 C 0.1695(3) 0.9488(6) 0.25459(8) 0.0206(7) Uani 1 1 d . . . . .
H4 H 0.131510 0.801695 0.246835 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1190(3) 1.0680(5) 0.28533(8) 0.0188(6) Uani 1 1 d . . . . .
Br1 Br 0.34584(3) 0.87895(6) 0.19477(2) 0.02764(11) Uani 1 1 d . . . . .
C7 C 0.0104(3) 0.9598(6) 0.30621(8) 0.0223(7) Uani 1 1 d . . . . .
H5 H -0.029353 0.815664 0.297626 0.027 Uiso 1 1 calc R U . . .
N1 N -0.0314(3) 1.0575(5) 0.33582(7) 0.0231(6) Uani 1 1 d . . . . .
C8 C -0.1375(3) 0.9338(6) 0.35566(8) 0.0235(7) Uani 1 1 d . . . . .
H6 H -0.193625 0.836399 0.337584 0.028 Uiso 1 1 calc R U . . .
H7 H -0.198040 1.050761 0.366520 0.028 Uiso 1 1 calc R U . . .
C9 C -0.0735(3) 0.7757(6) 0.38706(8) 0.0209(7) Uani 1 1 d . . . . .
H8 H -0.009215 0.664360 0.376401 0.025 Uiso 1 1 calc R U . . .
H9 H -0.021440 0.874228 0.405838 0.025 Uiso 1 1 calc R U . . .
C10 C -0.1832(3) 0.6371(6) 0.40633(8) 0.0214(6) Uani 1 1 d . . . . .
H10 H -0.242379 0.749731 0.418714 0.026 Uiso 1 1 calc R U . . .
H11 H -0.240858 0.552240 0.386969 0.026 Uiso 1 1 calc R U . . .
C11 C -0.1258(3) 0.4591(6) 0.43555(8) 0.0216(7) Uani 1 1 d . . . . .
H12 H -0.071582 0.544406 0.455581 0.026 Uiso 1 1 calc R U . . .
H13 H -0.063664 0.350118 0.423486 0.026 Uiso 1 1 calc R U . . .
C12 C -0.2371(3) 0.3153(6) 0.45326(8) 0.0221(7) Uani 1 1 d . . . . .
H14 H -0.299578 0.425036 0.465034 0.027 Uiso 1 1 calc R U . . .
H15 H -0.290815 0.229897 0.433156 0.027 Uiso 1 1 calc R U . . .
C13 C -0.1824(3) 0.1370(6) 0.48283(8) 0.0206(6) Uani 1 1 d . . . . .
H16 H -0.119556 0.027611 0.471106 0.025 Uiso 1 1 calc R U . . .
H17 H -0.129077 0.222381 0.503020 0.025 Uiso 1 1 calc R U . . .
C14 C -0.2933(3) -0.0063(6) 0.50020(8) 0.0217(7) Uani 1 1 d . . . . .
H18 H -0.346825 -0.091190 0.479995 0.026 Uiso 1 1 calc R U . . .
H19 H -0.355945 0.103088 0.511998 0.026 Uiso 1 1 calc R U . . .
C15 C -0.2386(3) -0.1856(5) 0.52973(8) 0.0207(7) Uani 1 1 d . . . . .
H20 H -0.176042 -0.294901 0.517907 0.025 Uiso 1 1 calc R U . . .
H21 H -0.185019 -0.100593 0.549897 0.025 Uiso 1 1 calc R U . . .
C16 C -0.3497(3) -0.3302(5) 0.54735(8) 0.0203(7) Uani 1 1 d . . . . .
H22 H -0.402656 -0.417354 0.527292 0.024 Uiso 1 1 calc R U . . .
H23 H -0.412974 -0.221342 0.559003 0.024 Uiso 1 1 calc R U . . .
C17 C -0.2929(3) -0.5072(6) 0.57724(8) 0.0232(7) Uani 1 1 d . . . . .
H24 H -0.230142 -0.616656 0.565518 0.028 Uiso 1 1 calc R U . . .
H25 H -0.239290 -0.420040 0.597172 0.028 Uiso 1 1 calc R U . . .
C18 C -0.4035(3) -0.6509(6) 0.59517(8) 0.0229(7) Uani 1 1 d . . . . .
H26 H -0.458988 -0.734150 0.575177 0.028 Uiso 1 1 calc R U . . .
H27 H -0.464440 -0.541891 0.607645 0.028 Uiso 1 1 calc R U . . .
C19 C -0.3458(3) -0.8320(6) 0.62397(9) 0.0251(7) Uani 1 1 d . . . . .
H28 H -0.288504 -0.749579 0.643676 0.030 Uiso 1 1 calc R U . . .
H29 H -0.286839 -0.943901 0.611388 0.030 Uiso 1 1 calc R U . . .
C20 C -0.4578(3) -0.9705(6) 0.64243(10) 0.0321(8) Uani 1 1 d . . . . .
H30 H -0.514433 -0.861485 0.655807 0.038 Uiso 1 1 calc R U . . .
H31 H -0.415604 -1.084864 0.660145 0.038 Uiso 1 1 calc R U . . .
H32 H -0.514693 -1.053428 0.623099 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.342(4) . ?
O1 H1 0.67(4) . ?
C1 C2 1.401(4) . ?
C1 C6 1.419(4) . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 Br1 1.916(3) . ?
C5 C6 1.411(4) . ?
C5 H4 0.9500 . ?
C6 C7 1.479(4) . ?
C7 N1 1.288(4) . ?
C7 H5 0.9500 . ?
N1 C8 1.480(4) . ?
C8 C9 1.539(4) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.537(4) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.535(4) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 C12 1.538(4) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
C12 C13 1.536(4) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C13 C14 1.528(4) . ?
C13 H16 0.9900 . ?
C13 H17 0.9900 . ?
C14 C15 1.539(4) . ?
C14 H18 0.9900 . ?
C14 H19 0.9900 . ?
C15 C16 1.537(4) . ?
C15 H20 0.9900 . ?
C15 H21 0.9900 . ?
C16 C17 1.545(4) . ?
C16 H22 0.9900 . ?
C16 H23 0.9900 . ?
C17 C18 1.536(4) . ?
C17 H24 0.9900 . ?
C17 H25 0.9900 . ?
C18 C19 1.538(4) . ?
C18 H26 0.9900 . ?
C18 H27 0.9900 . ?
C19 C20 1.539(4) . ?
C19 H28 0.9900 . ?
C19 H29 0.9900 . ?
C20 H30 0.9800 . ?
C20 H31 0.9800 . ?
C20 H32 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105(4) . . ?
O1 C1 C2 118.6(3) . . ?
O1 C1 C6 121.6(3) . . ?
C2 C1 C6 119.8(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 Br1 120.0(2) . . ?
C3 C4 Br1 119.6(2) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H4 119.9 . . ?
C6 C5 H4 119.9 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 120.0(3) . . ?
C1 C6 C7 120.8(3) . . ?
N1 C7 C6 121.3(3) . . ?
N1 C7 H5 119.4 . . ?
C6 C7 H5 119.4 . . ?
C7 N1 C8 117.7(3) . . ?
N1 C8 C9 111.2(2) . . ?
N1 C8 H6 109.4 . . ?
C9 C8 H6 109.4 . . ?
N1 C8 H7 109.4 . . ?
C9 C8 H7 109.4 . . ?
H6 C8 H7 108.0 . . ?
C10 C9 C8 111.3(2) . . ?
C10 C9 H8 109.4 . . ?
C8 C9 H8 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
H8 C9 H9 108.0 . . ?
C11 C10 C9 114.0(2) . . ?
C11 C10 H10 108.8 . . ?
C9 C10 H10 108.8 . . ?
C11 C10 H11 108.8 . . ?
C9 C10 H11 108.8 . . ?
H10 C10 H11 107.6 . . ?
C10 C11 C12 113.1(2) . . ?
C10 C11 H12 109.0 . . ?
C12 C11 H12 109.0 . . ?
C10 C11 H13 109.0 . . ?
C12 C11 H13 109.0 . . ?
H12 C11 H13 107.8 . . ?
C13 C12 C11 114.2(2) . . ?
C13 C12 H14 108.7 . . ?
C11 C12 H14 108.7 . . ?
C13 C12 H15 108.7 . . ?
C11 C12 H15 108.7 . . ?
H14 C12 H15 107.6 . . ?
C14 C13 C12 114.0(2) . . ?
C14 C13 H16 108.8 . . ?
C12 C13 H16 108.8 . . ?
C14 C13 H17 108.8 . . ?
C12 C13 H17 108.8 . . ?
H16 C13 H17 107.7 . . ?
C13 C14 C15 114.0(2) . . ?
C13 C14 H18 108.7 . . ?
C15 C14 H18 108.7 . . ?
C13 C14 H19 108.7 . . ?
C15 C14 H19 108.7 . . ?
H18 C14 H19 107.6 . . ?
C16 C15 C14 114.3(2) . . ?
C16 C15 H20 108.7 . . ?
C14 C15 H20 108.7 . . ?
C16 C15 H21 108.7 . . ?
C14 C15 H21 108.7 . . ?
H20 C15 H21 107.6 . . ?
C15 C16 C17 113.5(2) . . ?
C15 C16 H22 108.9 . . ?
C17 C16 H22 108.9 . . ?
C15 C16 H23 108.9 . . ?
C17 C16 H23 108.9 . . ?
H22 C16 H23 107.7 . . ?
C18 C17 C16 113.8(2) . . ?
C18 C17 H24 108.8 . . ?
C16 C17 H24 108.8 . . ?
C18 C17 H25 108.8 . . ?
C16 C17 H25 108.8 . . ?
H24 C17 H25 107.7 . . ?
C17 C18 C19 113.4(3) . . ?
C17 C18 H26 108.9 . . ?
C19 C18 H26 108.9 . . ?
C17 C18 H27 108.9 . . ?
C19 C18 H27 108.9 . . ?
H26 C18 H27 107.7 . . ?
C18 C19 C20 112.9(3) . . ?
C18 C19 H28 109.0 . . ?
C20 C19 H28 109.0 . . ?
C18 C19 H29 109.0 . . ?
C20 C19 H29 109.0 . . ?
H28 C19 H29 107.8 . . ?
C19 C20 H30 109.5 . . ?
C19 C20 H31 109.5 . . ?
H30 C20 H31 109.5 . . ?
C19 C20 H32 109.5 . . ?
H30 C20 H32 109.5 . . ?
H31 C20 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.6(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 Br1 -178.8(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
Br1 C4 C5 C6 178.3(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -177.9(3) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
O1 C1 C6 C7 -1.5(4) . . . . ?
C2 C1 C6 C7 178.3(3) . . . . ?
C5 C6 C7 N1 175.5(3) . . . . ?
C1 C6 C7 N1 -3.1(4) . . . . ?
C6 C7 N1 C8 -178.2(3) . . . . ?
C7 N1 C8 C9 93.0(3) . . . . ?
N1 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 174.7(3) . . . . ?
C9 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C13 C14 C15 C16 179.9(3) . . . . ?
C14 C15 C16 C17 -179.3(3) . . . . ?
C15 C16 C17 C18 179.6(3) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C17 C18 C19 C20 178.6(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
O1 H1 N1 0.67(4) 1.98(4) 2.607(4) 157(5) .

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.090


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1566478'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Br N O'
_chemical_formula_sum            'C14 H12 Br N O'
_chemical_formula_weight         290.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.100(11)
_cell_length_b                   5.993(4)
_cell_length_c                   29.53(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.576(7)
_cell_angle_gamma                90
_cell_volume                     2435(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.357
_shelx_estimated_absorpt_T_min   0.326
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            16441
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.773
_diffrn_reflns_theta_max         25.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             4252
_reflns_number_gt                3165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4252
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6229(3) 0.2250(6) 0.55002(12) 0.0269(8) Uani 1 1 d . . . . .
H1 H 0.660(5) 0.313(10) 0.570(2) 0.07(2) Uiso 1 1 d . . . . .
C1 C 0.6110(3) 0.3249(8) 0.50795(16) 0.0211(11) Uani 1 1 d . . . . .
C2 C 0.5626(3) 0.2109(8) 0.46850(16) 0.0228(11) Uani 1 1 d . . . . .
H2 H 0.538370 0.064799 0.471289 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5497(3) 0.3105(8) 0.42521(16) 0.0252(12) Uani 1 1 d . . . . .
H3 H 0.517056 0.232290 0.398342 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5844(3) 0.5234(8) 0.42114(15) 0.0233(11) Uani 1 1 d . . . . .
C5 C 0.6327(3) 0.6393(8) 0.45929(15) 0.0211(11) Uani 1 1 d . . . . .
H4 H 0.657126 0.784515 0.455759 0.025 Uiso 1 1 calc R U . . .
C6 C 0.6459(3) 0.5431(7) 0.50359(15) 0.0190(11) Uani 1 1 d . . . . .
Br1 Br 0.56371(4) 0.65951(9) 0.36158(2) 0.0354(2) Uani 1 1 d . . . . .
C7 C 0.6930(3) 0.6722(8) 0.54457(16) 0.0215(11) Uani 1 1 d . . . . .
H5 H 0.713029 0.820984 0.540645 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7076(3) 0.5900(6) 0.58514(12) 0.0219(9) Uani 1 1 d . . . . .
C8 C 0.7536(3) 0.7345(8) 0.62392(15) 0.0251(12) Uani 1 1 d . . . . .
H6 H 0.753142 0.890802 0.613037 0.030 Uiso 1 1 calc R U . . .
H7 H 0.822049 0.688526 0.635344 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7000(3) 0.7197(8) 0.66315(15) 0.0199(11) Uani 1 1 d . . . . .
C10 C 0.6410(3) 0.8934(8) 0.67177(15) 0.0243(12) Uani 1 1 d . . . . .
H8 H 0.633278 1.022598 0.652684 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5935(3) 0.8788(8) 0.70809(15) 0.0270(12) Uani 1 1 d . . . . .
H9 H 0.552814 0.997833 0.713442 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6045(3) 0.6936(8) 0.73662(16) 0.0283(12) Uani 1 1 d . . . . .
H10 H 0.572542 0.685672 0.761784 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6628(3) 0.5194(8) 0.72792(15) 0.0267(12) Uani 1 1 d . . . . .
H11 H 0.669972 0.389887 0.746908 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7109(3) 0.5329(8) 0.69169(15) 0.0243(12) Uani 1 1 d . . . . .
H12 H 0.751514 0.413659 0.686364 0.029 Uiso 1 1 calc R U . . .
O2 O 0.8779(2) -0.3059(5) 0.44836(11) 0.0248(8) Uani 1 1 d . . . . .
H13 H 0.838(3) -0.212(7) 0.4218(16) 0.027(13) Uiso 1 1 d . . . . .
C15 C 0.8877(3) -0.1823(7) 0.48746(15) 0.0194(11) Uani 1 1 d . . . . .
C16 C 0.9380(3) -0.2734(7) 0.52983(15) 0.0203(11) Uani 1 1 d . . . . .
H14 H 0.963496 -0.420445 0.530754 0.024 Uiso 1 1 calc R U . . .
C17 C 0.9501(3) -0.1496(8) 0.56990(16) 0.0216(11) Uani 1 1 d . . . . .
H15 H 0.985486 -0.210015 0.598335 0.026 Uiso 1 1 calc R U . . .
C18 C 0.9110(3) 0.0630(8) 0.56896(15) 0.0215(11) Uani 1 1 d . . . . .
C19 C 0.8615(3) 0.1562(8) 0.52831(16) 0.0216(11) Uani 1 1 d . . . . .
H16 H 0.835479 0.302400 0.528246 0.026 Uiso 1 1 calc R U . . .
C20 C 0.8493(3) 0.0352(7) 0.48679(15) 0.0193(11) Uani 1 1 d . . . . .
Br2 Br 0.93023(4) 0.23032(9) 0.62512(2) 0.03198(19) Uani 1 1 d . . . . .
C21 C 0.8005(3) 0.1419(8) 0.44290(16) 0.0212(11) Uani 1 1 d . . . . .
H17 H 0.777507 0.290808 0.443251 0.025 Uiso 1 1 calc R U . . .
N2 N 0.7887(3) 0.0376(7) 0.40459(13) 0.0252(10) Uani 1 1 d . . . . .
C22 C 0.7409(4) 0.1590(9) 0.36197(16) 0.0317(13) Uani 1 1 d . . . . .
H18 H 0.725496 0.312931 0.370185 0.038 Uiso 1 1 calc R U . . .
H19 H 0.679050 0.083692 0.347727 0.038 Uiso 1 1 calc R U . . .
C23 C 0.8057(3) 0.1669(8) 0.32735(16) 0.0217(11) Uani 1 1 d . . . . .
C24 C 0.8653(3) 0.3488(8) 0.32601(15) 0.0249(12) Uani 1 1 d . . . . .
H20 H 0.864976 0.469770 0.346780 0.030 Uiso 1 1 calc R U . . .
C25 C 0.9256(4) 0.3566(8) 0.29457(16) 0.0264(12) Uani 1 1 d . . . . .
H21 H 0.965538 0.483473 0.293589 0.032 Uiso 1 1 calc R U . . .
C26 C 0.9276(4) 0.1793(8) 0.26466(15) 0.0264(12) Uani 1 1 d . . . . .
H22 H 0.969779 0.182527 0.243593 0.032 Uiso 1 1 calc R U . . .
C27 C 0.8677(3) -0.0020(8) 0.26572(16) 0.0274(12) Uani 1 1 d . . . . .
H23 H 0.868253 -0.122910 0.244965 0.033 Uiso 1 1 calc R U . . .
C28 C 0.8069(3) -0.0094(8) 0.29675(16) 0.0280(12) Uani 1 1 d . . . . .
H24 H 0.765979 -0.134952 0.297164 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.356(6) . ?
O1 H1 0.87(6) . ?
C1 C2 1.394(6) . ?
C1 C6 1.412(6) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 Br1 1.903(5) . ?
C5 C6 1.404(6) . ?
C5 H4 0.9500 . ?
C6 C7 1.468(6) . ?
C7 N1 1.270(6) . ?
C7 H5 0.9500 . ?
N1 C8 1.469(5) . ?
C8 C9 1.517(6) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C14 1.389(6) . ?
C9 C10 1.390(6) . ?
C10 C11 1.386(6) . ?
C10 H8 0.9500 . ?
C11 C12 1.382(7) . ?
C11 H9 0.9500 . ?
C12 C13 1.388(7) . ?
C12 H10 0.9500 . ?
C13 C14 1.388(6) . ?
C13 H11 0.9500 . ?
C14 H12 0.9500 . ?
O2 C15 1.353(5) . ?
O2 H13 1.03(5) . ?
C15 C16 1.407(6) . ?
C15 C20 1.410(6) . ?
C16 C17 1.376(6) . ?
C16 H14 0.9500 . ?
C17 C18 1.386(6) . ?
C17 H15 0.9500 . ?
C18 C19 1.369(6) . ?
C18 Br2 1.906(5) . ?
C19 C20 1.402(6) . ?
C19 H16 0.9500 . ?
C20 C21 1.475(6) . ?
C21 N2 1.272(6) . ?
C21 H17 0.9500 . ?
N2 C22 1.483(6) . ?
C22 C23 1.513(6) . ?
C22 H18 0.9900 . ?
C22 H19 0.9900 . ?
C23 C24 1.382(7) . ?
C23 C28 1.393(7) . ?
C24 C25 1.390(6) . ?
C24 H20 0.9500 . ?
C25 C26 1.386(6) . ?
C25 H21 0.9500 . ?
C26 C27 1.380(7) . ?
C26 H22 0.9500 . ?
C27 C28 1.385(6) . ?
C27 H23 0.9500 . ?
C28 H24 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
C1 O1 H1 106(4) . . ?
O1 C1 C2 119.3(4) . . ?
O1 C1 C6 121.1(4) . . ?
C2 C1 C6 119.6(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 Br1 119.4(4) . . ?
C3 C4 Br1 119.4(3) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H4 120.1 . . ?
C6 C5 H4 120.1 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 C7 119.7(4) . . ?
C1 C6 C7 121.1(4) . . ?
N1 C7 C6 121.6(4) . . ?
N1 C7 H5 119.2 . . ?
C6 C7 H5 119.2 . . ?
C7 N1 C8 117.4(4) . . ?
N1 C8 C9 110.6(4) . . ?
N1 C8 H6 109.5 . . ?
C9 C8 H6 109.5 . . ?
N1 C8 H7 109.5 . . ?
C9 C8 H7 109.5 . . ?
H6 C8 H7 108.1 . . ?
C14 C9 C10 118.9(4) . . ?
C14 C9 C8 120.2(4) . . ?
C10 C9 C8 120.9(4) . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H8 119.9 . . ?
C9 C10 H8 119.9 . . ?
C12 C11 C10 120.9(5) . . ?
C12 C11 H9 119.5 . . ?
C10 C11 H9 119.5 . . ?
C11 C12 C13 118.9(5) . . ?
C11 C12 H10 120.5 . . ?
C13 C12 H10 120.5 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H11 119.7 . . ?
C12 C13 H11 119.7 . . ?
C13 C14 C9 120.4(5) . . ?
C13 C14 H12 119.8 . . ?
C9 C14 H12 119.8 . . ?
C15 O2 H13 107(2) . . ?
O2 C15 C16 119.0(4) . . ?
O2 C15 C20 121.8(4) . . ?
C16 C15 C20 119.3(4) . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H14 120.0 . . ?
C15 C16 H14 120.0 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H15 119.9 . . ?
C18 C17 H15 119.9 . . ?
C19 C18 C17 121.1(4) . . ?
C19 C18 Br2 119.8(4) . . ?
C17 C18 Br2 119.1(3) . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H16 120.1 . . ?
C20 C19 H16 120.1 . . ?
C19 C20 C15 119.5(4) . . ?
C19 C20 C21 119.3(4) . . ?
C15 C20 C21 121.2(4) . . ?
N2 C21 C20 121.0(4) . . ?
N2 C21 H17 119.5 . . ?
C20 C21 H17 119.5 . . ?
C21 N2 C22 117.5(4) . . ?
N2 C22 C23 111.0(4) . . ?
N2 C22 H18 109.4 . . ?
C23 C22 H18 109.4 . . ?
N2 C22 H19 109.4 . . ?
C23 C22 H19 109.4 . . ?
H18 C22 H19 108.0 . . ?
C24 C23 C28 119.1(5) . . ?
C24 C23 C22 120.3(4) . . ?
C28 C23 C22 120.6(5) . . ?
C23 C24 C25 120.7(5) . . ?
C23 C24 H20 119.7 . . ?
C25 C24 H20 119.7 . . ?
C26 C25 C24 120.0(5) . . ?
C26 C25 H21 120.0 . . ?
C24 C25 H21 120.0 . . ?
C27 C26 C25 119.5(5) . . ?
C27 C26 H22 120.3 . . ?
C25 C26 H22 120.3 . . ?
C26 C27 C28 120.6(5) . . ?
C26 C27 H23 119.7 . . ?
C28 C27 H23 119.7 . . ?
C27 C28 C23 120.1(5) . . ?
C27 C28 H24 119.9 . . ?
C23 C28 H24 119.9 . . ?

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
O1 C1 C2 C3 180.0(4) . . . . ?
C6 C1 C2 C3 0.7(7) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C2 C3 C4 Br1 -178.7(3) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
Br1 C4 C5 C6 178.2(3) . . . . ?
C4 C5 C6 C1 1.5(7) . . . . ?
C4 C5 C6 C7 -176.7(4) . . . . ?
O1 C1 C6 C5 179.5(4) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
O1 C1 C6 C7 -2.3(7) . . . . ?
C2 C1 C6 C7 177.0(4) . . . . ?
C5 C6 C7 N1 -178.9(4) . . . . ?
C1 C6 C7 N1 2.8(7) . . . . ?
C6 C7 N1 C8 -178.9(4) . . . . ?
C7 N1 C8 C9 133.9(4) . . . . ?
N1 C8 C9 C14 75.2(5) . . . . ?
N1 C8 C9 C10 -106.1(5) . . . . ?
C14 C9 C10 C11 -0.5(7) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
C11 C12 C13 C14 1.2(7) . . . . ?
C12 C13 C14 C9 -1.0(7) . . . . ?
C10 C9 C14 C13 0.6(7) . . . . ?
C8 C9 C14 C13 179.4(4) . . . . ?
O2 C15 C16 C17 179.0(4) . . . . ?
C20 C15 C16 C17 -0.7(7) . . . . ?
C15 C16 C17 C18 1.5(7) . . . . ?
C16 C17 C18 C19 -1.4(7) . . . . ?
C16 C17 C18 Br2 -179.6(3) . . . . ?
C17 C18 C19 C20 0.4(7) . . . . ?
Br2 C18 C19 C20 178.5(3) . . . . ?
C18 C19 C20 C15 0.5(7) . . . . ?
C18 C19 C20 C21 -176.7(4) . . . . ?
O2 C15 C20 C19 -180.0(4) . . . . ?
C16 C15 C20 C19 -0.3(7) . . . . ?
O2 C15 C20 C21 -2.8(7) . . . . ?
C16 C15 C20 C21 176.8(4) . . . . ?
C19 C20 C21 N2 179.6(4) . . . . ?
C15 C20 C21 N2 2.4(7) . . . . ?
C20 C21 N2 C22 -178.7(4) . . . . ?
C21 N2 C22 C23 122.0(5) . . . . ?
N2 C22 C23 C24 -94.5(5) . . . . ?
N2 C22 C23 C28 84.9(5) . . . . ?
C28 C23 C24 C25 0.1(7) . . . . ?
C22 C23 C24 C25 179.5(4) . . . . ?
C23 C24 C25 C26 -1.0(7) . . . . ?
C24 C25 C26 C27 1.4(7) . . . . ?
C25 C26 C27 C28 -0.9(7) . . . . ?
C26 C27 C28 C23 -0.1(7) . . . . ?
C24 C23 C28 C27 0.5(7) . . . . ?
C22 C23 C28 C27 -178.9(4) . . . . ?

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
O1 H1 N1 0.87(6) 1.81(6) 2.597(5) 149(6) .
O2 H13 N2 1.03(5) 1.68(4) 2.604(5) 147(4) .

_refine_diff_density_max         0.689
_refine_diff_density_min         -1.096
_refine_diff_density_rms         0.116


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1566472'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_shelxl              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal diffracted quite weakly at high angle region,
maybe due to the low quality of the crystal.
No obvious diffraction peaks were observed at 2 theta > 45 degree.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          316
_chemical_formula_moiety         'C20 H32 Br N O'
_chemical_formula_sum            'C20 H32 Br N O'
_chemical_formula_weight         382.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9934(16)
_cell_length_b                   5.7714(8)
_cell_length_c                   35.925(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.957(8)
_cell_angle_gamma                90
_cell_volume                     2067.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    2388
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      22.40

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.994
_shelx_estimated_absorpt_T_min   0.424
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            10536
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         22.429
_diffrn_reflns_theta_full        22.429
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2676
_reflns_number_gt                2146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2676
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1283(3) 1.3774(4) 0.32511(8) 0.0703(8) Uani 1 1 d . . . . .
H1 H 0.078504 1.293777 0.336395 0.105 Uiso 1 1 calc R U . . .
C1 C 0.1739(4) 1.2596(7) 0.29625(10) 0.0505(9) Uani 1 1 d . . . . .
C2 C 0.2776(4) 1.3534(6) 0.27672(11) 0.0564(10) Uani 1 1 d . . . . .
H2 H 0.313765 1.496647 0.283739 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3267(3) 1.2356(7) 0.24718(10) 0.0550(10) Uani 1 1 d . . . . .
H3 H 0.395691 1.299594 0.234421 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2733(3) 1.0208(6) 0.23640(10) 0.0508(9) Uani 1 1 d . . . . .
C5 C 0.1701(3) 0.9249(6) 0.25512(10) 0.0488(9) Uani 1 1 d . . . . .
H4 H 0.134204 0.782424 0.247561 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1195(3) 1.0409(6) 0.28535(10) 0.0463(9) Uani 1 1 d . . . . .
Br1 Br 0.34530(4) 0.85637(7) 0.19607(2) 0.0726(2) Uani 1 1 d . . . . .
C7 C 0.0120(3) 0.9346(7) 0.30601(11) 0.0540(10) Uani 1 1 d . . . . .
H5 H -0.025570 0.795079 0.297590 0.065 Uiso 1 1 calc R U . . .
N1 N -0.0306(3) 1.0293(5) 0.33511(8) 0.0554(8) Uani 1 1 d . . . . .
C8 C -0.1345(4) 0.9038(7) 0.35461(11) 0.0644(11) Uani 1 1 d . . . . .
H6 H -0.185122 0.804971 0.336918 0.077 Uiso 1 1 calc R U . . .
H7 H -0.196127 1.014926 0.364257 0.077 Uiso 1 1 calc R U . . .
C9 C -0.0740(3) 0.7563(7) 0.38663(10) 0.0545(9) Uani 1 1 d . . . . .
H8 H -0.026253 0.855797 0.404812 0.065 Uiso 1 1 calc R U . . .
H9 H -0.009790 0.649076 0.377153 0.065 Uiso 1 1 calc R U . . .
C10 C -0.1815(3) 0.6191(6) 0.40586(10) 0.0555(10) Uani 1 1 d . . . . .
H10 H -0.240304 0.727976 0.417250 0.067 Uiso 1 1 calc R U . . .
H11 H -0.235214 0.533588 0.387002 0.067 Uiso 1 1 calc R U . . .
C11 C -0.1267(3) 0.4502(6) 0.43554(10) 0.0560(10) Uani 1 1 d . . . . .
H12 H -0.076895 0.536269 0.455125 0.067 Uiso 1 1 calc R U . . .
H13 H -0.064564 0.345615 0.424517 0.067 Uiso 1 1 calc R U . . .
C12 C -0.2359(3) 0.3065(6) 0.45302(10) 0.0547(10) Uani 1 1 d . . . . .
H14 H -0.298283 0.411579 0.463829 0.066 Uiso 1 1 calc R U . . .
H15 H -0.285379 0.220396 0.433378 0.066 Uiso 1 1 calc R U . . .
C13 C -0.1830(4) 0.1363(6) 0.48310(10) 0.0539(10) Uani 1 1 d . . . . .
H16 H -0.134791 0.222370 0.502965 0.065 Uiso 1 1 calc R U . . .
H17 H -0.119678 0.032362 0.472425 0.065 Uiso 1 1 calc R U . . .
C14 C -0.2926(3) -0.0089(6) 0.49994(10) 0.0542(10) Uani 1 1 d . . . . .
H18 H -0.355986 0.095070 0.510601 0.065 Uiso 1 1 calc R U . . .
H19 H -0.340794 -0.095021 0.480081 0.065 Uiso 1 1 calc R U . . .
C15 C -0.2399(4) -0.1787(6) 0.53000(10) 0.0553(10) Uani 1 1 d . . . . .
H20 H -0.191186 -0.092544 0.549765 0.066 Uiso 1 1 calc R U . . .
H21 H -0.176958 -0.283148 0.519284 0.066 Uiso 1 1 calc R U . . .
C16 C -0.3495(3) -0.3236(6) 0.54717(10) 0.0558(10) Uani 1 1 d . . . . .
H22 H -0.412936 -0.219382 0.557730 0.067 Uiso 1 1 calc R U . . .
H23 H -0.397672 -0.411225 0.527482 0.067 Uiso 1 1 calc R U . . .
C17 C -0.2955(3) -0.4917(6) 0.57754(10) 0.0557(10) Uani 1 1 d . . . . .
H24 H -0.232914 -0.596814 0.566818 0.067 Uiso 1 1 calc R U . . .
H25 H -0.246034 -0.403886 0.596964 0.067 Uiso 1 1 calc R U . . .
C18 C -0.4027(4) -0.6346(6) 0.59532(11) 0.0585(10) Uani 1 1 d . . . . .
H26 H -0.463729 -0.529445 0.606665 0.070 Uiso 1 1 calc R U . . .
H27 H -0.453896 -0.718664 0.575778 0.070 Uiso 1 1 calc R U . . .
C19 C -0.3494(4) -0.8067(6) 0.62469(11) 0.0630(11) Uani 1 1 d . . . . .
H28 H -0.295920 -0.723678 0.643905 0.076 Uiso 1 1 calc R U . . .
H29 H -0.290778 -0.915455 0.613206 0.076 Uiso 1 1 calc R U . . .
C20 C -0.4578(4) -0.9417(8) 0.64291(12) 0.0841(14) Uani 1 1 d . . . . .
H30 H -0.514930 -0.835953 0.655009 0.126 Uiso 1 1 calc R U . . .
H31 H -0.416893 -1.046763 0.661020 0.126 Uiso 1 1 calc R U . . .
H32 H -0.510055 -1.027628 0.624212 0.126 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.345(4) . ?
O1 H1 0.8200 . ?
C1 C2 1.400(5) . ?
C1 C6 1.419(5) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 Br1 1.913(3) . ?
C5 C6 1.400(5) . ?
C5 H4 0.9300 . ?
C6 C7 1.480(5) . ?
C7 N1 1.278(4) . ?
C7 H5 0.9300 . ?
N1 C8 1.481(4) . ?
C8 C9 1.522(5) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.536(5) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 C11 1.519(5) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
C11 C12 1.539(5) . ?
C11 H12 0.9700 . ?
C11 H13 0.9700 . ?
C12 C13 1.527(5) . ?
C12 H14 0.9700 . ?
C12 H15 0.9700 . ?
C13 C14 1.536(5) . ?
C13 H16 0.9700 . ?
C13 H17 0.9700 . ?
C14 C15 1.525(5) . ?
C14 H18 0.9700 . ?
C14 H19 0.9700 . ?
C15 C16 1.540(4) . ?
C15 H20 0.9700 . ?
C15 H21 0.9700 . ?
C16 C17 1.530(4) . ?
C16 H22 0.9700 . ?
C16 H23 0.9700 . ?
C17 C18 1.526(5) . ?
C17 H24 0.9700 . ?
C17 H25 0.9700 . ?
C18 C19 1.518(5) . ?
C18 H26 0.9700 . ?
C18 H27 0.9700 . ?
C19 C20 1.519(5) . ?
C19 H28 0.9700 . ?
C19 H29 0.9700 . ?
C20 H30 0.9600 . ?
C20 H31 0.9600 . ?
C20 H32 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.5(3) . . ?
O1 C1 C6 121.2(3) . . ?
C2 C1 C6 119.2(3) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 Br1 120.1(3) . . ?
C3 C4 Br1 119.6(3) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 120.5(3) . . ?
N1 C7 C6 121.8(4) . . ?
N1 C7 H5 119.1 . . ?
C6 C7 H5 119.1 . . ?
C7 N1 C8 117.5(3) . . ?
N1 C8 C9 112.1(3) . . ?
N1 C8 H6 109.2 . . ?
C9 C8 H6 109.2 . . ?
N1 C8 H7 109.2 . . ?
C9 C8 H7 109.2 . . ?
H6 C8 H7 107.9 . . ?
C8 C9 C10 112.0(3) . . ?
C8 C9 H8 109.2 . . ?
C10 C9 H8 109.2 . . ?
C8 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
H8 C9 H9 107.9 . . ?
C11 C10 C9 114.7(3) . . ?
C11 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C11 C10 H11 108.6 . . ?
C9 C10 H11 108.6 . . ?
H10 C10 H11 107.6 . . ?
C10 C11 C12 113.7(3) . . ?
C10 C11 H12 108.8 . . ?
C12 C11 H12 108.8 . . ?
C10 C11 H13 108.8 . . ?
C12 C11 H13 108.8 . . ?
H12 C11 H13 107.7 . . ?
C13 C12 C11 114.5(3) . . ?
C13 C12 H14 108.6 . . ?
C11 C12 H14 108.6 . . ?
C13 C12 H15 108.6 . . ?
C11 C12 H15 108.6 . . ?
H14 C12 H15 107.6 . . ?
C12 C13 C14 114.1(3) . . ?
C12 C13 H16 108.7 . . ?
C14 C13 H16 108.7 . . ?
C12 C13 H17 108.7 . . ?
C14 C13 H17 108.7 . . ?
H16 C13 H17 107.6 . . ?
C15 C14 C13 114.1(3) . . ?
C15 C14 H18 108.7 . . ?
C13 C14 H18 108.7 . . ?
C15 C14 H19 108.7 . . ?
C13 C14 H19 108.7 . . ?
H18 C14 H19 107.6 . . ?
C14 C15 C16 114.3(3) . . ?
C14 C15 H20 108.7 . . ?
C16 C15 H20 108.7 . . ?
C14 C15 H21 108.7 . . ?
C16 C15 H21 108.7 . . ?
H20 C15 H21 107.6 . . ?
C17 C16 C15 113.9(3) . . ?
C17 C16 H22 108.8 . . ?
C15 C16 H22 108.8 . . ?
C17 C16 H23 108.8 . . ?
C15 C16 H23 108.8 . . ?
H22 C16 H23 107.7 . . ?
C18 C17 C16 114.7(3) . . ?
C18 C17 H24 108.6 . . ?
C16 C17 H24 108.6 . . ?
C18 C17 H25 108.6 . . ?
C16 C17 H25 108.6 . . ?
H24 C17 H25 107.6 . . ?
C19 C18 C17 115.0(3) . . ?
C19 C18 H26 108.5 . . ?
C17 C18 H26 108.5 . . ?
C19 C18 H27 108.5 . . ?
C17 C18 H27 108.5 . . ?
H26 C18 H27 107.5 . . ?
C18 C19 C20 114.1(3) . . ?
C18 C19 H28 108.7 . . ?
C20 C19 H28 108.7 . . ?
C18 C19 H29 108.7 . . ?
C20 C19 H29 108.7 . . ?
H28 C19 H29 107.6 . . ?
C19 C20 H30 109.5 . . ?
C19 C20 H31 109.5 . . ?
H30 C20 H31 109.5 . . ?
C19 C20 H32 109.5 . . ?
H30 C20 H32 109.5 . . ?
H31 C20 H32 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.6(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 Br1 -178.6(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
Br1 C4 C5 C6 178.1(2) . . . . ?
C4 C5 C6 C1 0.9(5) . . . . ?
C4 C5 C6 C7 -178.2(3) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
O1 C1 C6 C7 -1.0(5) . . . . ?
C2 C1 C6 C7 178.5(3) . . . . ?
C5 C6 C7 N1 175.6(3) . . . . ?
C1 C6 C7 N1 -3.4(5) . . . . ?
C6 C7 N1 C8 -177.5(3) . . . . ?
C7 N1 C8 C9 94.8(4) . . . . ?
N1 C8 C9 C10 -177.8(3) . . . . ?
C8 C9 C10 C11 174.2(3) . . . . ?
C9 C10 C11 C12 -177.2(3) . . . . ?
C10 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C14 -179.1(3) . . . . ?
C12 C13 C14 C15 -180.0(3) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 -179.5(3) . . . . ?
C15 C16 C17 C18 179.2(3) . . . . ?
C16 C17 C18 C19 178.3(3) . . . . ?
C17 C18 C19 C20 178.2(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
O1 H1 N1 0.82 1.87 2.601(4) 147.0 .

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1566474'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          326
_chemical_formula_moiety         'C22 H36 Br N O'
_chemical_formula_sum            'C22 H36 Br N O'
_chemical_formula_weight         410.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.912(8)
_cell_length_b                   5.689(4)
_cell_length_c                   39.13(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.81(2)
_cell_angle_gamma                90
_cell_volume                     2195(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    1446
_cell_measurement_theta_min      34.80
_cell_measurement_theta_max      68.00

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.602
_shelx_estimated_absorpt_T_min   0.463
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            25186
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.1199
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.484
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3965
_reflns_number_gt                3063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1438P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3965
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0819
_refine_ls_wR_factor_ref         0.2545
_refine_ls_wR_factor_gt          0.2313
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6393(5) 1.0347(5) 0.31869(10) 0.0975(10) Uani 1 1 d . . . . .
H1 H 0.586733 0.952764 0.328374 0.146 Uiso 1 1 calc R U . . .
C1 C 0.6806(5) 0.9177(8) 0.29246(11) 0.0808(10) Uani 1 1 d . . . . .
C2 C 0.7826(6) 1.0124(7) 0.27443(13) 0.0848(12) Uani 1 1 d . . . . .
H2 H 0.820272 1.157035 0.281093 0.102 Uiso 1 1 calc R U . . .
C3 C 0.8274(5) 0.8984(8) 0.24760(11) 0.0860(11) Uani 1 1 d . . . . .
H3 H 0.894963 0.964753 0.235837 0.103 Uiso 1 1 calc R U . . .
C4 C 0.7724(4) 0.6812(7) 0.23752(10) 0.0784(10) Uani 1 1 d . . . . .
C5 C 0.6705(5) 0.5813(7) 0.25472(10) 0.0789(10) Uani 1 1 d . . . . .
H4 H 0.633286 0.436869 0.247757 0.095 Uiso 1 1 calc R U . . .
C6 C 0.6251(4) 0.6983(7) 0.28212(9) 0.0739(9) Uani 1 1 d . . . . .
Br1 Br 0.83854(6) 0.51348(9) 0.20053(2) 0.0980(3) Uani 1 1 d . . . . .
C7 C 0.5194(5) 0.5916(8) 0.30123(11) 0.0820(10) Uani 1 1 d . . . . .
H5 H 0.480434 0.449965 0.293554 0.098 Uiso 1 1 calc R U . . .
N1 N 0.4804(4) 0.6868(7) 0.32764(9) 0.0847(9) Uani 1 1 d . . . . .
C8 C 0.3771(6) 0.5647(9) 0.34578(12) 0.0925(12) Uani 1 1 d . . . . .
H6 H 0.321711 0.466635 0.329650 0.111 Uiso 1 1 calc R U . . .
H7 H 0.318370 0.679907 0.354994 0.111 Uiso 1 1 calc R U . . .
C9 C 0.4425(5) 0.4132(8) 0.37485(11) 0.0832(10) Uani 1 1 d . . . . .
H8 H 0.504919 0.303519 0.365834 0.100 Uiso 1 1 calc R U . . .
H9 H 0.493997 0.512381 0.391618 0.100 Uiso 1 1 calc R U . . .
C10 C 0.3370(5) 0.2783(7) 0.39219(10) 0.0839(11) Uani 1 1 d . . . . .
H10 H 0.280920 0.190685 0.374866 0.101 Uiso 1 1 calc R U . . .
H11 H 0.278897 0.389687 0.402450 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3956(5) 0.1084(7) 0.41983(10) 0.0824(10) Uani 1 1 d . . . . .
H12 H 0.447536 0.196263 0.437895 0.099 Uiso 1 1 calc R U . . .
H13 H 0.457044 0.001053 0.409957 0.099 Uiso 1 1 calc R U . . .
C12 C 0.2857(5) -0.0337(7) 0.43547(12) 0.0804(10) Uani 1 1 d . . . . .
H14 H 0.224392 0.074074 0.445297 0.096 Uiso 1 1 calc R U . . .
H15 H 0.233675 -0.120754 0.417331 0.096 Uiso 1 1 calc R U . . .
C13 C 0.3422(4) -0.2047(7) 0.46306(10) 0.0807(10) Uani 1 1 d . . . . .
H16 H 0.392738 -0.117450 0.481422 0.097 Uiso 1 1 calc R U . . .
H17 H 0.404777 -0.310750 0.453360 0.097 Uiso 1 1 calc R U . . .
C14 C 0.2322(5) -0.3493(7) 0.47811(10) 0.0812(10) Uani 1 1 d . . . . .
H18 H 0.169305 -0.243080 0.487658 0.097 Uiso 1 1 calc R U . . .
H19 H 0.181980 -0.437071 0.459743 0.097 Uiso 1 1 calc R U . . .
C15 C 0.2882(5) -0.5207(7) 0.50602(12) 0.0794(11) Uani 1 1 d . . . . .
H20 H 0.351304 -0.626610 0.496479 0.095 Uiso 1 1 calc R U . . .
H21 H 0.338244 -0.432853 0.524404 0.095 Uiso 1 1 calc R U . . .
C16 C 0.1790(4) -0.6651(7) 0.52095(10) 0.0813(10) Uani 1 1 d . . . . .
H22 H 0.129168 -0.753385 0.502577 0.098 Uiso 1 1 calc R U . . .
H23 H 0.115738 -0.559199 0.530422 0.098 Uiso 1 1 calc R U . . .
C17 C 0.2350(5) -0.8355(7) 0.54889(10) 0.0812(10) Uani 1 1 d . . . . .
H24 H 0.298058 -0.941534 0.539346 0.097 Uiso 1 1 calc R U . . .
H25 H 0.285317 -0.747037 0.567159 0.097 Uiso 1 1 calc R U . . .
C18 C 0.1268(5) -0.9803(7) 0.56416(12) 0.0816(11) Uani 1 1 d . . . . .
H26 H 0.063672 -0.874789 0.573778 0.098 Uiso 1 1 calc R U . . .
H27 H 0.076474 -1.069480 0.545958 0.098 Uiso 1 1 calc R U . . .
C19 C 0.1845(5) -1.1482(7) 0.59185(11) 0.0843(11) Uani 1 1 d . . . . .
H28 H 0.236131 -1.058767 0.609789 0.101 Uiso 1 1 calc R U . . .
H29 H 0.246729 -1.254580 0.582069 0.101 Uiso 1 1 calc R U . . .
C20 C 0.0780(5) -1.2930(8) 0.60796(11) 0.0855(11) Uani 1 1 d . . . . .
H30 H 0.016860 -1.186806 0.618181 0.103 Uiso 1 1 calc R U . . .
H31 H 0.025137 -1.380114 0.589975 0.103 Uiso 1 1 calc R U . . .
C21 C 0.1366(6) -1.4641(8) 0.63516(13) 0.0890(12) Uani 1 1 d . . . . .
H32 H 0.192076 -1.378347 0.652818 0.107 Uiso 1 1 calc R U . . .
H33 H 0.194820 -1.574893 0.624816 0.107 Uiso 1 1 calc R U . . .
C22 C 0.0276(6) -1.5994(10) 0.65171(15) 0.1089(16) Uani 1 1 d . . . . .
H34 H -0.021460 -1.697690 0.634806 0.163 Uiso 1 1 calc R U . . .
H35 H -0.033718 -1.490529 0.660729 0.163 Uiso 1 1 calc R U . . .
H36 H 0.069392 -1.695240 0.670011 0.163 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.323(6) . ?
O1 H1 0.8200 . ?
C1 C2 1.398(7) . ?
C1 C6 1.407(6) . ?
C2 C3 1.347(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 Br1 1.904(4) . ?
C5 C6 1.376(6) . ?
C5 H4 0.9300 . ?
C6 C7 1.478(6) . ?
C7 N1 1.262(6) . ?
C7 H5 0.9300 . ?
N1 C8 1.477(6) . ?
C8 C9 1.519(6) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.512(6) . ?
C9 H8 0.9700 . ?
C9 H9 0.9700 . ?
C10 C11 1.521(5) . ?
C10 H10 0.9700 . ?
C10 H11 0.9700 . ?
C11 C12 1.533(6) . ?
C11 H12 0.9700 . ?
C11 H13 0.9700 . ?
C12 C13 1.517(6) . ?
C12 H14 0.9700 . ?
C12 H15 0.9700 . ?
C13 C14 1.530(6) . ?
C13 H16 0.9700 . ?
C13 H17 0.9700 . ?
C14 C15 1.526(6) . ?
C14 H18 0.9700 . ?
C14 H19 0.9700 . ?
C15 C16 1.522(6) . ?
C15 H20 0.9700 . ?
C15 H21 0.9700 . ?
C16 C17 1.523(5) . ?
C16 H22 0.9700 . ?
C16 H23 0.9700 . ?
C17 C18 1.522(6) . ?
C17 H24 0.9700 . ?
C17 H25 0.9700 . ?
C18 C19 1.513(6) . ?
C18 H26 0.9700 . ?
C18 H27 0.9700 . ?
C19 C20 1.525(6) . ?
C19 H28 0.9700 . ?
C19 H29 0.9700 . ?
C20 C21 1.514(6) . ?
C20 H30 0.9700 . ?
C20 H31 0.9700 . ?
C21 C22 1.523(7) . ?
C21 H32 0.9700 . ?
C21 H33 0.9700 . ?
C22 H34 0.9600 . ?
C22 H35 0.9600 . ?
C22 H36 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.6(4) . . ?
O1 C1 C6 121.8(4) . . ?
C2 C1 C6 118.6(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 Br1 119.1(3) . . ?
C3 C4 Br1 120.4(3) . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H4 120.3 . . ?
C4 C5 H4 120.3 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 C7 120.0(4) . . ?
C1 C6 C7 119.7(4) . . ?
N1 C7 C6 122.0(4) . . ?
N1 C7 H5 119.0 . . ?
C6 C7 H5 119.0 . . ?
C7 N1 C8 118.5(4) . . ?
N1 C8 C9 111.3(4) . . ?
N1 C8 H6 109.4 . . ?
C9 C8 H6 109.4 . . ?
N1 C8 H7 109.4 . . ?
C9 C8 H7 109.4 . . ?
H6 C8 H7 108.0 . . ?
C10 C9 C8 111.2(4) . . ?
C10 C9 H8 109.4 . . ?
C8 C9 H8 109.4 . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
H8 C9 H9 108.0 . . ?
C9 C10 C11 114.2(4) . . ?
C9 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C9 C10 H11 108.7 . . ?
C11 C10 H11 108.7 . . ?
H10 C10 H11 107.6 . . ?
C10 C11 C12 112.6(4) . . ?
C10 C11 H12 109.1 . . ?
C12 C11 H12 109.1 . . ?
C10 C11 H13 109.1 . . ?
C12 C11 H13 109.1 . . ?
H12 C11 H13 107.8 . . ?
C13 C12 C11 113.4(4) . . ?
C13 C12 H14 108.9 . . ?
C11 C12 H14 108.9 . . ?
C13 C12 H15 108.9 . . ?
C11 C12 H15 108.9 . . ?
H14 C12 H15 107.7 . . ?
C12 C13 C14 113.1(4) . . ?
C12 C13 H16 109.0 . . ?
C14 C13 H16 109.0 . . ?
C12 C13 H17 109.0 . . ?
C14 C13 H17 109.0 . . ?
H16 C13 H17 107.8 . . ?
C15 C14 C13 113.4(4) . . ?
C15 C14 H18 108.9 . . ?
C13 C14 H18 108.9 . . ?
C15 C14 H19 108.9 . . ?
C13 C14 H19 108.9 . . ?
H18 C14 H19 107.7 . . ?
C16 C15 C14 113.5(4) . . ?
C16 C15 H20 108.9 . . ?
C14 C15 H20 108.9 . . ?
C16 C15 H21 108.9 . . ?
C14 C15 H21 108.9 . . ?
H20 C15 H21 107.7 . . ?
C15 C16 C17 113.4(4) . . ?
C15 C16 H22 108.9 . . ?
C17 C16 H22 108.9 . . ?
C15 C16 H23 108.9 . . ?
C17 C16 H23 108.9 . . ?
H22 C16 H23 107.7 . . ?
C18 C17 C16 114.0(4) . . ?
C18 C17 H24 108.8 . . ?
C16 C17 H24 108.8 . . ?
C18 C17 H25 108.8 . . ?
C16 C17 H25 108.8 . . ?
H24 C17 H25 107.7 . . ?
C19 C18 C17 113.1(4) . . ?
C19 C18 H26 109.0 . . ?
C17 C18 H26 109.0 . . ?
C19 C18 H27 109.0 . . ?
C17 C18 H27 109.0 . . ?
H26 C18 H27 107.8 . . ?
C18 C19 C20 114.2(4) . . ?
C18 C19 H28 108.7 . . ?
C20 C19 H28 108.7 . . ?
C18 C19 H29 108.7 . . ?
C20 C19 H29 108.7 . . ?
H28 C19 H29 107.6 . . ?
C21 C20 C19 113.9(4) . . ?
C21 C20 H30 108.8 . . ?
C19 C20 H30 108.8 . . ?
C21 C20 H31 108.8 . . ?
C19 C20 H31 108.8 . . ?
H30 C20 H31 107.7 . . ?
C20 C21 C22 112.7(5) . . ?
C20 C21 H32 109.1 . . ?
C22 C21 H32 109.1 . . ?
C20 C21 H33 109.1 . . ?
C22 C21 H33 109.1 . . ?
H32 C21 H33 107.8 . . ?
C21 C22 H34 109.5 . . ?
C21 C22 H35 109.5 . . ?
H34 C22 H35 109.5 . . ?
C21 C22 H36 109.5 . . ?
H34 C22 H36 109.5 . . ?
H35 C22 H36 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.9(5) . . . . ?
C6 C1 C2 C3 0.2(7) . . . . ?
C1 C2 C3 C4 -0.4(8) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C2 C3 C4 Br1 -178.1(4) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
Br1 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 -178.4(4) . . . . ?
O1 C1 C6 C5 -180.0(4) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
O1 C1 C6 C7 -1.1(7) . . . . ?
C2 C1 C6 C7 178.6(4) . . . . ?
C5 C6 C7 N1 176.0(4) . . . . ?
C1 C6 C7 N1 -2.9(6) . . . . ?
C6 C7 N1 C8 -178.2(4) . . . . ?
C7 N1 C8 C9 93.8(5) . . . . ?
N1 C8 C9 C10 -177.0(4) . . . . ?
C8 C9 C10 C11 175.6(4) . . . . ?
C9 C10 C11 C12 -177.1(4) . . . . ?
C10 C11 C12 C13 179.9(4) . . . . ?
C11 C12 C13 C14 -178.9(4) . . . . ?
C12 C13 C14 C15 -179.7(4) . . . . ?
C13 C14 C15 C16 -179.9(4) . . . . ?
C14 C15 C16 C17 -179.8(4) . . . . ?
C15 C16 C17 C18 179.7(4) . . . . ?
C16 C17 C18 C19 -180.0(4) . . . . ?
C17 C18 C19 C20 179.1(4) . . . . ?
C18 C19 C20 C21 178.8(4) . . . . ?
C19 C20 C21 C22 177.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.84 2.575(5) 148.1 .

_refine_diff_density_max         0.613
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1566476'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          332
_chemical_formula_moiety         'C24 H40 Br N O'
_chemical_formula_sum            'C24 H40 Br N O'
_chemical_formula_weight         438.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.739(9)
_cell_length_b                   5.587(5)
_cell_length_c                   42.62(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.40(2)
_cell_angle_gamma                90
_cell_volume                     2305(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1272
_cell_measurement_theta_min      16.90
_cell_measurement_theta_max      48.60

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.510
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.514
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            25576
_diffrn_reflns_av_unetI/netI     0.1212
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         70.139
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4424
_reflns_number_gt                3251
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1909P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4424
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.1065
_refine_ls_wR_factor_ref         0.3209
_refine_ls_wR_factor_gt          0.2571
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3406(9) -0.7368(11) 0.68636(14) 0.0649(18) Uani 1 1 d . . . . .
H1 H 0.273627 -0.658202 0.677540 0.097 Uiso 1 1 calc R U . . .
C1 C 0.3976(12) -0.6185(16) 0.7110(2) 0.060(2) Uani 1 1 d . . . . .
C2 C 0.5202(10) -0.7130(16) 0.72803(19) 0.054(2) Uani 1 1 d . . . . .
H2 H 0.555985 -0.861340 0.721685 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5866(10) -0.5947(17) 0.75313(18) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.666838 -0.661855 0.764517 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5359(9) -0.3722(17) 0.76217(18) 0.0502(19) Uani 1 1 d . . . . .
C5 C 0.4167(10) -0.2761(14) 0.74657(19) 0.0505(19) Uani 1 1 d . . . . .
H4 H 0.380377 -0.130456 0.753661 0.061 Uiso 1 1 calc R U . . .
C6 C 0.3495(9) -0.3949(16) 0.72019(17) 0.0472(17) Uani 1 1 d . . . . .
Br1 Br 0.62954(11) -0.20533(18) 0.79696(2) 0.0592(4) Uani 1 1 d . . . . .
C7 C 0.2282(10) -0.2868(15) 0.70268(19) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.192604 -0.141138 0.709968 0.064 Uiso 1 1 calc R U . . .
N1 N 0.1690(8) -0.3844(13) 0.67778(15) 0.0500(16) Uani 1 1 d . . . . .
C8 C 0.0457(10) -0.2623(17) 0.66093(19) 0.055(2) Uani 1 1 d . . . . .
H6 H -0.000442 -0.164548 0.676053 0.066 Uiso 1 1 calc R U . . .
H7 H -0.021045 -0.383290 0.651604 0.066 Uiso 1 1 calc R U . . .
C9 C 0.0912(10) -0.1008(15) 0.63470(18) 0.0517(19) Uani 1 1 d . . . . .
H8 H 0.161432 0.014882 0.643924 0.062 Uiso 1 1 calc R U . . .
H9 H 0.133435 -0.199796 0.619065 0.062 Uiso 1 1 calc R U . . .
C10 C -0.0332(10) 0.0343(16) 0.61833(17) 0.054(2) Uani 1 1 d . . . . .
H10 H -0.079614 0.121920 0.634372 0.065 Uiso 1 1 calc R U . . .
H11 H -0.100076 -0.082167 0.607905 0.065 Uiso 1 1 calc R U . . .
C11 C 0.0083(10) 0.2123(14) 0.59364(19) 0.051(2) Uani 1 1 d . . . . .
H12 H 0.079870 0.322101 0.603702 0.061 Uiso 1 1 calc R U . . .
H13 H 0.048389 0.123774 0.576722 0.061 Uiso 1 1 calc R U . . .
C12 C -0.1152(10) 0.3574(16) 0.57926(18) 0.053(2) Uani 1 1 d . . . . .
H14 H -0.154695 0.444994 0.596348 0.064 Uiso 1 1 calc R U . . .
H15 H -0.186898 0.245971 0.569605 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0811(10) 0.5373(16) 0.55421(18) 0.054(2) Uani 1 1 d . . . . .
H16 H -0.041266 0.450018 0.537150 0.064 Uiso 1 1 calc R U . . .
H17 H -0.009938 0.649560 0.563873 0.064 Uiso 1 1 calc R U . . .
C14 C -0.2062(9) 0.6816(14) 0.53973(18) 0.0484(19) Uani 1 1 d . . . . .
H18 H -0.277451 0.569782 0.529992 0.058 Uiso 1 1 calc R U . . .
H19 H -0.246115 0.769432 0.556734 0.058 Uiso 1 1 calc R U . . .
C15 C -0.1702(10) 0.8596(16) 0.51487(17) 0.0505(19) Uani 1 1 d . . . . .
H20 H -0.131034 0.771322 0.497797 0.061 Uiso 1 1 calc R U . . .
H21 H -0.098137 0.970041 0.524581 0.061 Uiso 1 1 calc R U . . .
C16 C -0.2939(10) 1.0065(17) 0.50048(19) 0.0531(19) Uani 1 1 d . . . . .
H22 H -0.365899 0.895754 0.490778 0.064 Uiso 1 1 calc R U . . .
H23 H -0.333164 1.094188 0.517585 0.064 Uiso 1 1 calc R U . . .
C17 C -0.2591(11) 1.1855(14) 0.47559(18) 0.054(2) Uani 1 1 d . . . . .
H24 H -0.187292 1.296518 0.485301 0.065 Uiso 1 1 calc R U . . .
H25 H -0.219621 1.097862 0.458506 0.065 Uiso 1 1 calc R U . . .
C18 C -0.3824(10) 1.3313(16) 0.46120(19) 0.054(2) Uani 1 1 d . . . . .
H26 H -0.421291 1.420549 0.478232 0.065 Uiso 1 1 calc R U . . .
H27 H -0.454607 1.220456 0.451649 0.065 Uiso 1 1 calc R U . . .
C19 C -0.3467(10) 1.5086(15) 0.43604(17) 0.0530(19) Uani 1 1 d . . . . .
H28 H -0.307417 1.419466 0.419055 0.064 Uiso 1 1 calc R U . . .
H29 H -0.274803 1.619949 0.445615 0.064 Uiso 1 1 calc R U . . .
C20 C -0.4716(10) 1.6552(16) 0.42139(18) 0.054(2) Uani 1 1 d . . . . .
H30 H -0.543727 1.544845 0.411662 0.064 Uiso 1 1 calc R U . . .
H31 H -0.511030 1.745657 0.438251 0.064 Uiso 1 1 calc R U . . .
C21 C -0.4315(10) 1.8302(15) 0.39635(18) 0.052(2) Uani 1 1 d . . . . .
H32 H -0.391494 1.739079 0.379636 0.062 Uiso 1 1 calc R U . . .
H33 H -0.359368 1.939997 0.406177 0.062 Uiso 1 1 calc R U . . .
C22 C -0.5546(10) 1.9790(16) 0.38116(18) 0.056(2) Uani 1 1 d . . . . .
H34 H -0.625014 1.869582 0.370541 0.068 Uiso 1 1 calc R U . . .
H35 H -0.597060 2.064811 0.397965 0.068 Uiso 1 1 calc R U . . .
C23 C -0.5135(10) 2.1594(17) 0.35733(18) 0.054(2) Uani 1 1 d . . . . .
H36 H -0.468273 2.075196 0.340809 0.065 Uiso 1 1 calc R U . . .
H37 H -0.446033 2.273760 0.368016 0.065 Uiso 1 1 calc R U . . .
C24 C -0.6426(13) 2.3004(18) 0.3415(2) 0.066(3) Uani 1 1 d . . . . .
H38 H -0.700831 2.348344 0.357799 0.098 Uiso 1 1 calc R U . . .
H39 H -0.695857 2.197491 0.326026 0.098 Uiso 1 1 calc R U . . .
H40 H -0.611773 2.443197 0.330976 0.098 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.311(12) . ?
O1 H1 0.8400 . ?
C1 C6 1.404(12) . ?
C1 C2 1.427(13) . ?
C2 C3 1.358(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(12) . ?
C4 Br1 1.897(8) . ?
C5 C6 1.403(11) . ?
C5 H4 0.9500 . ?
C6 C7 1.457(11) . ?
C7 N1 1.272(12) . ?
C7 H5 0.9500 . ?
N1 C8 1.494(11) . ?
C8 C9 1.540(11) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.529(12) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.534(11) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 C12 1.522(12) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
C12 C13 1.529(11) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C13 C14 1.532(12) . ?
C13 H16 0.9900 . ?
C13 H17 0.9900 . ?
C14 C15 1.522(11) . ?
C14 H18 0.9900 . ?
C14 H19 0.9900 . ?
C15 C16 1.529(13) . ?
C15 H20 0.9900 . ?
C15 H21 0.9900 . ?
C16 C17 1.524(11) . ?
C16 H22 0.9900 . ?
C16 H23 0.9900 . ?
C17 C18 1.522(12) . ?
C17 H24 0.9900 . ?
C17 H25 0.9900 . ?
C18 C19 1.528(11) . ?
C18 H26 0.9900 . ?
C18 H27 0.9900 . ?
C19 C20 1.540(12) . ?
C19 H28 0.9900 . ?
C19 H29 0.9900 . ?
C20 C21 1.530(11) . ?
C20 H30 0.9900 . ?
C20 H31 0.9900 . ?
C21 C22 1.541(12) . ?
C21 H32 0.9900 . ?
C21 H33 0.9900 . ?
C22 C23 1.516(11) . ?
C22 H34 0.9900 . ?
C22 H35 0.9900 . ?
C23 C24 1.570(14) . ?
C23 H36 0.9900 . ?
C23 H37 0.9900 . ?
C24 H38 0.9800 . ?
C24 H39 0.9800 . ?
C24 H40 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C6 123.1(9) . . ?
O1 C1 C2 118.4(8) . . ?
C6 C1 C2 118.3(9) . . ?
C3 C2 C1 121.2(9) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.7(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.9(7) . . ?
C5 C4 Br1 119.4(7) . . ?
C3 C4 Br1 119.7(6) . . ?
C4 C5 C6 119.6(8) . . ?
C4 C5 H4 120.2 . . ?
C6 C5 H4 120.2 . . ?
C5 C6 C1 120.2(8) . . ?
C5 C6 C7 119.6(8) . . ?
C1 C6 C7 120.2(8) . . ?
N1 C7 C6 121.0(8) . . ?
N1 C7 H5 119.5 . . ?
C6 C7 H5 119.5 . . ?
C7 N1 C8 118.0(7) . . ?
N1 C8 C9 109.6(8) . . ?
N1 C8 H6 109.8 . . ?
C9 C8 H6 109.8 . . ?
N1 C8 H7 109.8 . . ?
C9 C8 H7 109.8 . . ?
H6 C8 H7 108.2 . . ?
C10 C9 C8 110.1(8) . . ?
C10 C9 H8 109.6 . . ?
C8 C9 H8 109.6 . . ?
C10 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
H8 C9 H9 108.2 . . ?
C9 C10 C11 112.2(8) . . ?
C9 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H11 109.2 . . ?
C11 C10 H11 109.2 . . ?
H10 C10 H11 107.9 . . ?
C12 C11 C10 111.4(8) . . ?
C12 C11 H12 109.3 . . ?
C10 C11 H12 109.3 . . ?
C12 C11 H13 109.3 . . ?
C10 C11 H13 109.3 . . ?
H12 C11 H13 108.0 . . ?
C11 C12 C13 114.1(8) . . ?
C11 C12 H14 108.7 . . ?
C13 C12 H14 108.7 . . ?
C11 C12 H15 108.7 . . ?
C13 C12 H15 108.7 . . ?
H14 C12 H15 107.6 . . ?
C12 C13 C14 113.7(8) . . ?
C12 C13 H16 108.8 . . ?
C14 C13 H16 108.8 . . ?
C12 C13 H17 108.8 . . ?
C14 C13 H17 108.8 . . ?
H16 C13 H17 107.7 . . ?
C15 C14 C13 113.0(8) . . ?
C15 C14 H18 109.0 . . ?
C13 C14 H18 109.0 . . ?
C15 C14 H19 109.0 . . ?
C13 C14 H19 109.0 . . ?
H18 C14 H19 107.8 . . ?
C14 C15 C16 113.4(8) . . ?
C14 C15 H20 108.9 . . ?
C16 C15 H20 108.9 . . ?
C14 C15 H21 108.9 . . ?
C16 C15 H21 108.9 . . ?
H20 C15 H21 107.7 . . ?
C17 C16 C15 113.9(9) . . ?
C17 C16 H22 108.8 . . ?
C15 C16 H22 108.8 . . ?
C17 C16 H23 108.8 . . ?
C15 C16 H23 108.8 . . ?
H22 C16 H23 107.7 . . ?
C18 C17 C16 113.9(9) . . ?
C18 C17 H24 108.8 . . ?
C16 C17 H24 108.8 . . ?
C18 C17 H25 108.8 . . ?
C16 C17 H25 108.8 . . ?
H24 C17 H25 107.7 . . ?
C17 C18 C19 113.5(8) . . ?
C17 C18 H26 108.9 . . ?
C19 C18 H26 108.9 . . ?
C17 C18 H27 108.9 . . ?
C19 C18 H27 108.9 . . ?
H26 C18 H27 107.7 . . ?
C18 C19 C20 113.4(8) . . ?
C18 C19 H28 108.9 . . ?
C20 C19 H28 108.9 . . ?
C18 C19 H29 108.9 . . ?
C20 C19 H29 108.9 . . ?
H28 C19 H29 107.7 . . ?
C21 C20 C19 111.8(8) . . ?
C21 C20 H30 109.3 . . ?
C19 C20 H30 109.3 . . ?
C21 C20 H31 109.3 . . ?
C19 C20 H31 109.3 . . ?
H30 C20 H31 107.9 . . ?
C20 C21 C22 113.0(8) . . ?
C20 C21 H32 109.0 . . ?
C22 C21 H32 109.0 . . ?
C20 C21 H33 109.0 . . ?
C22 C21 H33 109.0 . . ?
H32 C21 H33 107.8 . . ?
C23 C22 C21 112.9(8) . . ?
C23 C22 H34 109.0 . . ?
C21 C22 H34 109.0 . . ?
C23 C22 H35 109.0 . . ?
C21 C22 H35 109.0 . . ?
H34 C22 H35 107.8 . . ?
C22 C23 C24 111.2(8) . . ?
C22 C23 H36 109.4 . . ?
C24 C23 H36 109.4 . . ?
C22 C23 H37 109.4 . . ?
C24 C23 H37 109.4 . . ?
H36 C23 H37 108.0 . . ?
C23 C24 H38 109.5 . . ?
C23 C24 H39 109.5 . . ?
H38 C24 H39 109.5 . . ?
C23 C24 H40 109.5 . . ?
H38 C24 H40 109.5 . . ?
H39 C24 H40 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.8(9) . . . . ?
C6 C1 C2 C3 2.2(14) . . . . ?
C1 C2 C3 C4 -1.5(14) . . . . ?
C2 C3 C4 C5 2.3(14) . . . . ?
C2 C3 C4 Br1 -179.4(7) . . . . ?
C3 C4 C5 C6 -3.8(13) . . . . ?
Br1 C4 C5 C6 178.0(6) . . . . ?
C4 C5 C6 C1 4.5(13) . . . . ?
C4 C5 C6 C7 -176.6(8) . . . . ?
O1 C1 C6 C5 -179.0(9) . . . . ?
C2 C1 C6 C5 -3.6(13) . . . . ?
O1 C1 C6 C7 2.1(14) . . . . ?
C2 C1 C6 C7 177.4(8) . . . . ?
C5 C6 C7 N1 176.5(9) . . . . ?
C1 C6 C7 N1 -4.5(14) . . . . ?
C6 C7 N1 C8 -179.6(8) . . . . ?
C7 N1 C8 C9 93.9(9) . . . . ?
N1 C8 C9 C10 -177.3(7) . . . . ?
C8 C9 C10 C11 175.7(7) . . . . ?
C9 C10 C11 C12 -176.0(7) . . . . ?
C10 C11 C12 C13 -179.5(7) . . . . ?
C11 C12 C13 C14 179.7(7) . . . . ?
C12 C13 C14 C15 180.0(7) . . . . ?
C13 C14 C15 C16 -179.4(7) . . . . ?
C14 C15 C16 C17 179.9(7) . . . . ?
C15 C16 C17 C18 179.9(7) . . . . ?
C16 C17 C18 C19 -179.4(7) . . . . ?
C17 C18 C19 C20 179.7(7) . . . . ?
C18 C19 C20 C21 -180.0(7) . . . . ?
C19 C20 C21 C22 179.8(7) . . . . ?
C20 C21 C22 C23 177.6(7) . . . . ?
C21 C22 C23 C24 177.9(7) . . . . ?

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
O1 H1 N1 0.84 1.84 2.582(10) 146.7 .

_refine_diff_density_max         0.715
_refine_diff_density_min         -2.393
_refine_diff_density_rms         0.141


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1566477'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Br N O'
_chemical_formula_sum            'C14 H12 Br N O'
_chemical_formula_weight         290.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.730(6)
_cell_length_b                   6.093(2)
_cell_length_c                   14.524(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.290(8)
_cell_angle_gamma                90
_cell_volume                     1273.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2223
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.30

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.210
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            8727
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.871
_diffrn_reflns_theta_max         25.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2299
_reflns_number_gt                1189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2299
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1031(3) 0.7924(5) 0.1222(3) 0.0757(9) Uani 1 1 d . . . . .
H1 H 0.146(4) 0.709(8) 0.152(4) 0.10(2) Uiso 1 1 d . . . . .
C1 C 0.0219(3) 0.6806(7) 0.1117(3) 0.0569(11) Uani 1 1 d . . . . .
C2 C -0.0592(4) 0.7796(7) 0.0646(3) 0.0629(12) Uani 1 1 d . . . . .
H2 H -0.057050 0.920786 0.040823 0.075 Uiso 1 1 calc R U . . .
C3 C -0.1431(4) 0.6716(8) 0.0524(3) 0.0674(13) Uani 1 1 d . . . . .
H3 H -0.197207 0.739476 0.020302 0.081 Uiso 1 1 calc R U . . .
C4 C -0.1465(3) 0.4621(8) 0.0879(3) 0.0668(12) Uani 1 1 d . . . . .
C5 C -0.0668(3) 0.3604(7) 0.1358(3) 0.0611(12) Uani 1 1 d . . . . .
H4 H -0.070220 0.220133 0.160187 0.073 Uiso 1 1 calc R U . . .
C6 C 0.0192(3) 0.4666(6) 0.1482(2) 0.0523(11) Uani 1 1 d . . . . .
Br1 Br -0.26124(4) 0.31218(11) 0.07020(5) 0.1142(4) Uani 1 1 d . . . . .
C7 C 0.1036(4) 0.3523(8) 0.1949(3) 0.0674(13) Uani 1 1 d . . . . .
H5 H 0.099338 0.209353 0.216032 0.081 Uiso 1 1 calc R U . . .
N1 N 0.1828(3) 0.4438(7) 0.2075(2) 0.0753(11) Uani 1 1 d . . . . .
C8 C 0.2638(4) 0.3127(9) 0.2544(4) 0.0977(18) Uani 1 1 d . . . . .
H6 H 0.244289 0.163670 0.263527 0.117 Uiso 1 1 calc R U . . .
H7 H 0.289769 0.374899 0.315890 0.117 Uiso 1 1 calc R U . . .
C9 C 0.3365(3) 0.3100(8) 0.1962(3) 0.0652(12) Uani 1 1 d . . . . .
C10 C 0.3986(4) 0.4787(9) 0.1969(4) 0.0858(16) Uani 1 1 d . . . . .
H8 H 0.395534 0.600711 0.234599 0.103 Uiso 1 1 calc R U . . .
C11 C 0.4652(4) 0.4718(11) 0.1432(5) 0.1023(19) Uani 1 1 d . . . . .
H9 H 0.506281 0.588236 0.144743 0.123 Uiso 1 1 calc R U . . .
C12 C 0.4706(4) 0.2960(12) 0.0883(5) 0.0983(17) Uani 1 1 d . . . . .
H10 H 0.515789 0.290643 0.052337 0.118 Uiso 1 1 calc R U . . .
C13 C 0.4105(4) 0.1276(10) 0.0857(4) 0.0936(16) Uani 1 1 d . . . . .
H11 H 0.414008 0.007298 0.047176 0.112 Uiso 1 1 calc R U . . .
C14 C 0.3439(4) 0.1325(8) 0.1396(4) 0.0777(14) Uani 1 1 d . . . . .
H12 H 0.303549 0.014456 0.137633 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.357(5) . ?
O1 H1 0.86(5) . ?
C1 C2 1.382(6) . ?
C1 C6 1.411(5) . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C4 Br1 1.889(5) . ?
C5 C6 1.400(6) . ?
C5 H4 0.9300 . ?
C6 C7 1.461(6) . ?
C7 N1 1.270(6) . ?
C7 H5 0.9300 . ?
N1 C8 1.477(6) . ?
C8 C9 1.499(7) . ?
C8 H6 0.9700 . ?
C8 H7 0.9700 . ?
C9 C10 1.374(7) . ?
C9 C14 1.377(7) . ?
C10 C11 1.378(7) . ?
C10 H8 0.9300 . ?
C11 C12 1.347(8) . ?
C11 H9 0.9300 . ?
C12 C13 1.351(8) . ?
C12 H10 0.9300 . ?
C13 C14 1.379(7) . ?
C13 H11 0.9300 . ?
C14 H12 0.9300 . ?

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
C1 O1 H1 108(4) . . ?
O1 C1 C2 119.0(4) . . ?
O1 C1 C6 121.1(4) . . ?
C2 C1 C6 119.9(4) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 Br1 119.5(4) . . ?
C3 C4 Br1 119.9(4) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H4 119.8 . . ?
C6 C5 H4 119.8 . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 C7 119.8(4) . . ?
C1 C6 C7 121.7(4) . . ?
N1 C7 C6 121.5(4) . . ?
N1 C7 H5 119.2 . . ?
C6 C7 H5 119.2 . . ?
C7 N1 C8 117.1(5) . . ?
N1 C8 C9 110.4(4) . . ?
N1 C8 H6 109.6 . . ?
C9 C8 H6 109.6 . . ?
N1 C8 H7 109.6 . . ?
C9 C8 H7 109.6 . . ?
H6 C8 H7 108.1 . . ?
C10 C9 C14 117.0(5) . . ?
C10 C9 C8 122.8(5) . . ?
C14 C9 C8 120.2(5) . . ?
C9 C10 C11 121.7(5) . . ?
C9 C10 H8 119.2 . . ?
C11 C10 H8 119.2 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H9 120.1 . . ?
C10 C11 H9 120.1 . . ?
C11 C12 C13 120.0(6) . . ?
C11 C12 H10 120.0 . . ?
C13 C12 H10 120.0 . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 H11 119.7 . . ?
C14 C13 H11 119.7 . . ?
C9 C14 C13 120.8(5) . . ?
C9 C14 H12 119.6 . . ?
C13 C14 H12 119.6 . . ?

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
O1 C1 C2 C3 179.9(4) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C2 C3 C4 Br1 -179.4(3) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
Br1 C4 C5 C6 178.7(3) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C4 C5 C6 C7 -176.9(4) . . . . ?
O1 C1 C6 C5 179.5(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
O1 C1 C6 C7 -2.7(6) . . . . ?
C2 C1 C6 C7 177.4(4) . . . . ?
C5 C6 C7 N1 -179.9(4) . . . . ?
C1 C6 C7 N1 2.3(6) . . . . ?
C6 C7 N1 C8 -179.2(4) . . . . ?
C7 N1 C8 C9 126.8(5) . . . . ?
N1 C8 C9 C10 81.3(6) . . . . ?
N1 C8 C9 C14 -99.4(5) . . . . ?
C14 C9 C10 C11 0.2(7) . . . . ?
C8 C9 C10 C11 179.6(5) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C11 C12 C13 0.4(8) . . . . ?
C11 C12 C13 C14 -0.8(8) . . . . ?
C10 C9 C14 C13 -0.6(7) . . . . ?
C8 C9 C14 C13 -179.9(5) . . . . ?
C12 C13 C14 C9 0.9(8) . . . . ?

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
O1 H1 N1 0.86(5) 1.84(5) 2.609(5) 149(5) .

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_shelxl_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1566475'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          326
_chemical_formula_moiety         'C22 H36 Br N O'
_chemical_formula_sum            'C22 H36 Br N O'
_chemical_formula_weight         410.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.769(12)
_cell_length_b                   5.613(7)
_cell_length_c                   39.16(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.05(5)
_cell_angle_gamma                90
_cell_volume                     2135(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1135
_cell_measurement_theta_min      34.40
_cell_measurement_theta_max      68.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.675
_shelx_estimated_absorpt_T_min   0.472
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            21491
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.542
_diffrn_reflns_theta_max         68.173
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3760
_reflns_number_gt                3042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1178P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3760
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1937
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6433(3) 1.0739(5) 0.31910(7) 0.0474(7) Uani 1 1 d . . . . .
H1 H 0.589124 0.989568 0.329221 0.071 Uiso 1 1 calc R U . . .
C1 C 0.6835(5) 0.9533(7) 0.29262(10) 0.0405(9) Uani 1 1 d . . . . .
C2 C 0.7868(5) 1.0488(7) 0.27437(10) 0.0427(9) Uani 1 1 d . . . . .
H2 H 0.826360 1.198322 0.281182 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8327(4) 0.9307(7) 0.24663(9) 0.0428(9) Uani 1 1 d . . . . .
H3 H 0.903186 0.996898 0.234598 0.051 Uiso 1 1 calc R U . . .
C4 C 0.7726(4) 0.7112(7) 0.23680(8) 0.0428(9) Uani 1 1 d . . . . .
C5 C 0.6696(4) 0.6133(7) 0.25421(9) 0.0409(8) Uani 1 1 d . . . . .
H4 H 0.629430 0.465330 0.246884 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6247(4) 0.7301(7) 0.28232(8) 0.0396(8) Uani 1 1 d . . . . .
Br1 Br 0.83840(4) 0.54226(8) 0.19927(2) 0.0474(2) Uani 1 1 d . . . . .
C7 C 0.5170(4) 0.6223(7) 0.30127(9) 0.0411(9) Uani 1 1 d . . . . .
H5 H 0.474190 0.478168 0.293144 0.049 Uiso 1 1 calc R U . . .
N1 N 0.4803(4) 0.7202(6) 0.32849(7) 0.0430(8) Uani 1 1 d . . . . .
C8 C 0.3749(4) 0.5990(8) 0.34651(9) 0.0454(9) Uani 1 1 d . . . . .
H6 H 0.315365 0.501132 0.329975 0.054 Uiso 1 1 calc R U . . .
H7 H 0.316379 0.719196 0.356434 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4430(4) 0.4398(7) 0.37512(9) 0.0411(9) Uani 1 1 d . . . . .
H8 H 0.498755 0.539230 0.392233 0.049 Uiso 1 1 calc R U . . .
H9 H 0.505543 0.325724 0.365316 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3353(4) 0.3023(7) 0.39289(9) 0.0421(9) Uani 1 1 d . . . . .
H10 H 0.278153 0.417996 0.404159 0.051 Uiso 1 1 calc R U . . .
H11 H 0.274072 0.217055 0.375182 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3947(4) 0.1223(7) 0.41967(8) 0.0411(8) Uani 1 1 d . . . . .
H12 H 0.451441 0.208204 0.438169 0.049 Uiso 1 1 calc R U . . .
H13 H 0.455836 0.011377 0.408790 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2849(4) -0.0221(7) 0.43558(10) 0.0411(9) Uani 1 1 d . . . . .
H14 H 0.222870 0.089165 0.446113 0.049 Uiso 1 1 calc R U . . .
H15 H 0.229011 -0.109646 0.417094 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3430(4) -0.2002(7) 0.46278(9) 0.0420(9) Uani 1 1 d . . . . .
H16 H 0.397905 -0.112796 0.481461 0.050 Uiso 1 1 calc R U . . .
H17 H 0.405757 -0.310779 0.452366 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2317(4) -0.3454(7) 0.47818(8) 0.0407(8) Uani 1 1 d . . . . .
H18 H 0.168949 -0.234800 0.488579 0.049 Uiso 1 1 calc R U . . .
H19 H 0.176956 -0.432975 0.459516 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2899(4) -0.5229(7) 0.50538(9) 0.0397(9) Uani 1 1 d . . . . .
H20 H 0.345365 -0.435300 0.523937 0.048 Uiso 1 1 calc R U . . .
H21 H 0.352240 -0.634047 0.494920 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1790(4) -0.6679(7) 0.52113(9) 0.0418(9) Uani 1 1 d . . . . .
H22 H 0.116904 -0.556809 0.531694 0.050 Uiso 1 1 calc R U . . .
H23 H 0.123235 -0.754923 0.502566 0.050 Uiso 1 1 calc R U . . .
C17 C 0.2374(4) -0.8466(7) 0.54827(9) 0.0419(9) Uani 1 1 d . . . . .
H24 H 0.293444 -0.759318 0.566752 0.050 Uiso 1 1 calc R U . . .
H25 H 0.299272 -0.957622 0.537654 0.050 Uiso 1 1 calc R U . . .
C18 C 0.1275(4) -0.9919(7) 0.56428(9) 0.0411(9) Uani 1 1 d . . . . .
H26 H 0.065170 -0.881139 0.574789 0.049 Uiso 1 1 calc R U . . .
H27 H 0.071963 -1.080649 0.545871 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1875(4) -1.1685(7) 0.59159(9) 0.0423(9) Uani 1 1 d . . . . .
H28 H 0.243609 -1.079652 0.609895 0.051 Uiso 1 1 calc R U . . .
H29 H 0.249498 -1.279595 0.581021 0.051 Uiso 1 1 calc R U . . .
C20 C 0.0782(4) -1.3141(7) 0.60796(9) 0.0422(9) Uani 1 1 d . . . . .
H30 H 0.018631 -1.203891 0.619480 0.051 Uiso 1 1 calc R U . . .
H31 H 0.019516 -1.398108 0.589616 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1403(5) -1.4970(7) 0.63412(10) 0.0434(9) Uani 1 1 d . . . . .
H32 H 0.200875 -1.414076 0.652211 0.052 Uiso 1 1 calc R U . . .
H33 H 0.197577 -1.610678 0.622523 0.052 Uiso 1 1 calc R U . . .
C22 C 0.0289(4) -1.6356(8) 0.65087(10) 0.0496(10) Uani 1 1 d . . . . .
H34 H -0.028290 -1.724848 0.633199 0.060 Uiso 1 1 calc R U . . .
H35 H -0.028845 -1.523543 0.662124 0.060 Uiso 1 1 calc R U . . .
H36 H 0.072903 -1.746688 0.667955 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.332(5) . ?
O1 H1 0.8400 . ?
C1 C2 1.404(6) . ?
C1 C6 1.419(5) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(6) . ?
C4 Br1 1.916(4) . ?
C5 C6 1.391(5) . ?
C5 H4 0.9500 . ?
C6 C7 1.480(5) . ?
C7 N1 1.283(5) . ?
C7 H5 0.9500 . ?
N1 C8 1.474(5) . ?
C8 C9 1.530(5) . ?
C8 H6 0.9900 . ?
C8 H7 0.9900 . ?
C9 C10 1.530(5) . ?
C9 H8 0.9900 . ?
C9 H9 0.9900 . ?
C10 C11 1.526(5) . ?
C10 H10 0.9900 . ?
C10 H11 0.9900 . ?
C11 C12 1.528(5) . ?
C11 H12 0.9900 . ?
C11 H13 0.9900 . ?
C12 C13 1.526(5) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C13 C14 1.532(5) . ?
C13 H16 0.9900 . ?
C13 H17 0.9900 . ?
C14 C15 1.524(5) . ?
C14 H18 0.9900 . ?
C14 H19 0.9900 . ?
C15 C16 1.536(5) . ?
C15 H20 0.9900 . ?
C15 H21 0.9900 . ?
C16 C17 1.527(5) . ?
C16 H22 0.9900 . ?
C16 H23 0.9900 . ?
C17 C18 1.534(5) . ?
C17 H24 0.9900 . ?
C17 H25 0.9900 . ?
C18 C19 1.529(5) . ?
C18 H26 0.9900 . ?
C18 H27 0.9900 . ?
C19 C20 1.537(5) . ?
C19 H28 0.9900 . ?
C19 H29 0.9900 . ?
C20 C21 1.530(5) . ?
C20 H30 0.9900 . ?
C20 H31 0.9900 . ?
C21 C22 1.540(6) . ?
C21 H32 0.9900 . ?
C21 H33 0.9900 . ?
C22 H34 0.9800 . ?
C22 H35 0.9800 . ?
C22 H36 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.3(4) . . ?
O1 C1 C6 121.8(4) . . ?
C2 C1 C6 118.9(4) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 118.4(4) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 Br1 120.0(3) . . ?
C3 C4 Br1 118.8(3) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H4 119.7 . . ?
C6 C5 H4 119.7 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 C7 120.3(4) . . ?
C1 C6 C7 120.4(4) . . ?
N1 C7 C6 121.1(4) . . ?
N1 C7 H5 119.4 . . ?
C6 C7 H5 119.4 . . ?
C7 N1 C8 118.0(4) . . ?
N1 C8 C9 110.4(3) . . ?
N1 C8 H6 109.6 . . ?
C9 C8 H6 109.6 . . ?
N1 C8 H7 109.6 . . ?
C9 C8 H7 109.6 . . ?
H6 C8 H7 108.1 . . ?
C8 C9 C10 111.2(3) . . ?
C8 C9 H8 109.4 . . ?
C10 C9 H8 109.4 . . ?
C8 C9 H9 109.4 . . ?
C10 C9 H9 109.4 . . ?
H8 C9 H9 108.0 . . ?
C11 C10 C9 114.6(3) . . ?
C11 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C11 C10 H11 108.6 . . ?
C9 C10 H11 108.6 . . ?
H10 C10 H11 107.6 . . ?
C10 C11 C12 113.5(3) . . ?
C10 C11 H12 108.9 . . ?
C12 C11 H12 108.9 . . ?
C10 C11 H13 108.9 . . ?
C12 C11 H13 108.9 . . ?
H12 C11 H13 107.7 . . ?
C13 C12 C11 114.0(3) . . ?
C13 C12 H14 108.8 . . ?
C11 C12 H14 108.8 . . ?
C13 C12 H15 108.8 . . ?
C11 C12 H15 108.8 . . ?
H14 C12 H15 107.7 . . ?
C12 C13 C14 113.3(3) . . ?
C12 C13 H16 108.9 . . ?
C14 C13 H16 108.9 . . ?
C12 C13 H17 108.9 . . ?
C14 C13 H17 108.9 . . ?
H16 C13 H17 107.7 . . ?
C15 C14 C13 113.3(3) . . ?
C15 C14 H18 108.9 . . ?
C13 C14 H18 108.9 . . ?
C15 C14 H19 108.9 . . ?
C13 C14 H19 108.9 . . ?
H18 C14 H19 107.7 . . ?
C14 C15 C16 113.6(4) . . ?
C14 C15 H20 108.8 . . ?
C16 C15 H20 108.8 . . ?
C14 C15 H21 108.8 . . ?
C16 C15 H21 108.8 . . ?
H20 C15 H21 107.7 . . ?
C17 C16 C15 113.5(3) . . ?
C17 C16 H22 108.9 . . ?
C15 C16 H22 108.9 . . ?
C17 C16 H23 108.9 . . ?
C15 C16 H23 108.9 . . ?
H22 C16 H23 107.7 . . ?
C16 C17 C18 114.1(3) . . ?
C16 C17 H24 108.7 . . ?
C18 C17 H24 108.7 . . ?
C16 C17 H25 108.7 . . ?
C18 C17 H25 108.7 . . ?
H24 C17 H25 107.6 . . ?
C19 C18 C17 113.5(3) . . ?
C19 C18 H26 108.9 . . ?
C17 C18 H26 108.9 . . ?
C19 C18 H27 108.9 . . ?
C17 C18 H27 108.9 . . ?
H26 C18 H27 107.7 . . ?
C18 C19 C20 113.9(3) . . ?
C18 C19 H28 108.8 . . ?
C20 C19 H28 108.8 . . ?
C18 C19 H29 108.8 . . ?
C20 C19 H29 108.8 . . ?
H28 C19 H29 107.7 . . ?
C21 C20 C19 113.1(3) . . ?
C21 C20 H30 109.0 . . ?
C19 C20 H30 109.0 . . ?
C21 C20 H31 109.0 . . ?
C19 C20 H31 109.0 . . ?
H30 C20 H31 107.8 . . ?
C20 C21 C22 112.1(4) . . ?
C20 C21 H32 109.2 . . ?
C22 C21 H32 109.2 . . ?
C20 C21 H33 109.2 . . ?
C22 C21 H33 109.2 . . ?
H32 C21 H33 107.9 . . ?
C21 C22 H34 109.5 . . ?
C21 C22 H35 109.5 . . ?
H34 C22 H35 109.5 . . ?
C21 C22 H36 109.5 . . ?
H34 C22 H36 109.5 . . ?
H35 C22 H36 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.9(4) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C2 C3 C4 Br1 -178.4(3) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
Br1 C4 C5 C6 177.5(3) . . . . ?
C4 C5 C6 C1 1.2(6) . . . . ?
C4 C5 C6 C7 -178.7(3) . . . . ?
O1 C1 C6 C5 179.3(4) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
O1 C1 C6 C7 -0.8(6) . . . . ?
C2 C1 C6 C7 179.1(4) . . . . ?
C5 C6 C7 N1 175.7(4) . . . . ?
C1 C6 C7 N1 -4.2(6) . . . . ?
C6 C7 N1 C8 -178.4(3) . . . . ?
C7 N1 C8 C9 93.9(4) . . . . ?
N1 C8 C9 C10 -177.0(3) . . . . ?
C8 C9 C10 C11 174.8(3) . . . . ?
C9 C10 C11 C12 -176.8(3) . . . . ?
C10 C11 C12 C13 -179.1(3) . . . . ?
C11 C12 C13 C14 -179.4(3) . . . . ?
C12 C13 C14 C15 -179.9(3) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 179.7(3) . . . . ?
C15 C16 C17 C18 179.8(3) . . . . ?
C16 C17 C18 C19 -179.5(3) . . . . ?
C17 C18 C19 C20 179.7(3) . . . . ?
C18 C19 C20 C21 177.6(3) . . . . ?
C19 C20 C21 C22 178.4(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
O1 H1 N1 0.84 1.85 2.595(5) 147.6 .

_refine_diff_density_max         1.341
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.104


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
