# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1485934'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 Br'
_chemical_formula_sum            'C23 H31 Br'
_chemical_formula_weight         387.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.7174(12)
_cell_length_b                   6.5055(3)
_cell_length_c                   25.6670(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.802(5)
_cell_angle_gamma                90
_cell_volume                     3780.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1564
_cell_measurement_theta_min      3.2920
_cell_measurement_theta_max      26.5210

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.518
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            6317
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         28.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3741
_reflns_number_gt                2927
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0320P)²+8.5072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3741
_refine_ls_number_parameters     319
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.073
_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
Br1 Br 0.16339(2) 0.67730(6) 0.06561(2) 0.04109(16) Uani 0.8539(13) 1 d D U P A
1
C1 C 0.1930(2) 0.4390(6) 0.10554(18) 0.0242(10) Uani 0.8539(13) 1 d D U P A 1
C2 C 0.23519(15) 0.3384(6) 0.08603(12) 0.0246(8) Uani 0.8539(13) 1 d D U P A 1
C3 C 0.27822(15) 0.2389(6) 0.06652(13) 0.0245(8) Uani 0.8539(13) 1 d D U P A 1
H3A H 0.2679 0.1244 0.0447 0.029 Uiso 0.8539(13) 1 calc R U P A 1
C4 C 0.1637(2) 0.3935(6) 0.15460(19) 0.0193(10) Uani 0.8539(13) 1 d D U P A 1
C5 C 0.19301(14) 0.2012(5) 0.18124(13) 0.0224(7) Uani 0.8539(13) 1 d D U P A 1
H5A H 0.1883 0.0822 0.1572 0.027 Uiso 0.8539(13) 1 calc R U P A 1
H5B H 0.2358 0.2263 0.1894 0.027 Uiso 0.8539(13) 1 calc R U P A 1
C6 C 0.17163(15) 0.5746(5) 0.19302(13) 0.0235(8) Uani 0.8539(13) 1 d D U P A 1
H6A H 0.2143 0.6018 0.2014 0.028 Uiso 0.8539(13) 1 calc R U P A 1
H6B H 0.1534 0.6997 0.1766 0.028 Uiso 0.8539(13) 1 calc R U P A 1
C7 C 0.09745(14) 0.3495(6) 0.14249(13) 0.0242(8) Uani 0.8539(13) 1 d D U P A 1
H7A H 0.0779 0.4705 0.1252 0.029 Uiso 0.8539(13) 1 calc R U P A 1
H7B H 0.0922 0.2311 0.1183 0.029 Uiso 0.8539(13) 1 calc R U P A 1
C8 C 0.1641(2) 0.1533(8) 0.2318(2) 0.0259(12) Uani 0.8539(13) 1 d D U P A 1
H8A H 0.1833 0.0293 0.2489 0.031 Uiso 0.8539(13) 1 calc R U P A 1
C9 C 0.1427(2) 0.5261(8) 0.2435(2) 0.0267(12) Uani 0.8539(13) 1 d D U P A 1
H9A H 0.1478 0.6457 0.2679 0.032 Uiso 0.8539(13) 1 calc R U P A 1
C10 C 0.0688(2) 0.3015(7) 0.1932(2) 0.0290(11) Uani 0.8539(13) 1 d D U P A 1
H10A H 0.0257 0.2744 0.1849 0.035 Uiso 0.8539(13) 1 calc R U P A 1
C11 C 0.17141(16) 0.3361(6) 0.26939(14) 0.0277(8) Uani 0.8539(13) 1 d D U P A 1
H11A H 0.1527 0.3045 0.3019 0.033 Uiso 0.8539(13) 1 calc R U P A 1
H11B H 0.2139 0.3624 0.2787 0.033 Uiso 0.8539(13) 1 calc R U P A 1
C12 C 0.07663(16) 0.4841(6) 0.23062(16) 0.0277(9) Uani 0.8539(13) 1 d D U P A 1
H12A H 0.0578 0.4535 0.2632 0.033 Uiso 0.8539(13) 1 calc R U P A 1
H12B H 0.0573 0.6073 0.2143 0.033 Uiso 0.8539(13) 1 calc R U P A 1
C13 C 0.09815(16) 0.1107(6) 0.21897(17) 0.0289(9) Uani 0.8539(13) 1 d D U P A 1
H13A H 0.0794 0.0771 0.2514 0.035 Uiso 0.8539(13) 1 calc R U P A 1
H13B H 0.0929 -0.0083 0.1950 0.035 Uiso 0.8539(13) 1 calc R U P A 1
C14 C 0.3427(2) 0.2905(10) 0.0757(2) 0.0231(13) Uani 0.8539(13) 1 d D U P A 1
C15 C 0.35502(15) 0.4718(6) 0.11298(13) 0.0267(8) Uani 0.8539(13) 1 d D U P A 1
H15A H 0.3333 0.5944 0.0989 0.032 Uiso 0.8539(13) 1 calc R U P A 1
H15B H 0.3407 0.4386 0.1474 0.032 Uiso 0.8539(13) 1 calc R U P A 1
C16 C 0.37675(16) 0.1017(6) 0.09890(15) 0.0297(8) Uani 0.8539(13) 1 d D U P A 1
H16A H 0.3625 0.0666 0.1332 0.036 Uiso 0.8539(13) 1 calc R U P A 1
H16B H 0.3694 -0.0178 0.0753 0.036 Uiso 0.8539(13) 1 calc R U P A 1
C17 C 0.3669(2) 0.3429(8) 0.02310(18) 0.0287(11) Uani 0.8539(13) 1 d D U P A 1
H17A H 0.3595 0.2264 -0.0014 0.034 Uiso 0.8539(13) 1 calc R U P A 1
H17B H 0.3461 0.4650 0.0077 0.034 Uiso 0.8539(13) 1 calc R U P A 1
C18 C 0.42097(19) 0.5196(8) 0.11988(18) 0.0307(11) Uani 0.8539(13) 1 d D U P A
1
H18A H 0.4282 0.6387 0.1442 0.037 Uiso 0.8539(13) 1 calc R U P A 1
C19 C 0.44308(19) 0.1469(7) 0.1057(2) 0.0395(11) Uani 0.8539(13) 1 d D U P A 1
H19A H 0.4645 0.0234 0.1208 0.047 Uiso 0.8539(13) 1 calc R U P A 1
C20 C 0.43298(17) 0.3864(6) 0.03031(14) 0.0341(9) Uani 0.8539(13) 1 d D U P A 1
H20A H 0.4476 0.4206 -0.0043 0.041 Uiso 0.8539(13) 1 calc R U P A 1
C21 C 0.45362(17) 0.3277(7) 0.14303(15) 0.0410(10) Uani 0.8539(13) 1 d D U P A
1
H21A H 0.4965 0.3564 0.1486 0.049 Uiso 0.8539(13) 1 calc R U P A 1
H21B H 0.4390 0.2935 0.1773 0.049 Uiso 0.8539(13) 1 calc R U P A 1
C22 C 0.46580(17) 0.1987(7) 0.05307(18) 0.0408(11) Uani 0.8539(13) 1 d D U P A
1
H22A H 0.5087 0.2275 0.0576 0.049 Uiso 0.8539(13) 1 calc R U P A 1
H22B H 0.4593 0.0807 0.0289 0.049 Uiso 0.8539(13) 1 calc R U P A 1
C23 C 0.44402(18) 0.5691(7) 0.06742(16) 0.0335(10) Uani 0.8539(13) 1 d D U P A
1
H23A H 0.4869 0.5987 0.0723 0.040 Uiso 0.8539(13) 1 calc R U P A 1
H23B H 0.4237 0.6925 0.0522 0.040 Uiso 0.8539(13) 1 calc R U P A 1
Br1' Br 0.21778(13) 0.6986(4) 0.08418(11) 0.0488(10) Uani 0.1461(13) 1 d D U P
A 2
C1' C 0.1834(13) 0.428(3) 0.0928(7) 0.024(8) Uiso 0.1461(13) 1 d D U P A 2
C2' C 0.1809(9) 0.312(3) 0.0515(6) 0.032(5) Uiso 0.1461(13) 1 d D U P A 2
C3' C 0.1759(8) 0.189(3) 0.0105(6) 0.033(5) Uiso 0.1461(13) 1 d D U P A 2
H3'A H 0.2057 0.0881 0.0079 0.040 Uiso 0.1461(13) 1 calc R U P A 2
C4' C 0.1574(10) 0.384(3) 0.1438(7) 0.023(8) Uiso 0.1461(13) 1 d D U P A 2
C5' C 0.1303(8) 0.164(3) 0.1414(6) 0.029(4) Uiso 0.1461(13) 1 d D U P A 2
H5'A H 0.1611 0.0626 0.1344 0.035 Uiso 0.1461(13) 1 calc R U P A 2
H5'B H 0.0985 0.1566 0.1126 0.035 Uiso 0.1461(13) 1 calc R U P A 2
C6' C 0.1090(8) 0.536(3) 0.1552(7) 0.036(5) Uiso 0.1461(13) 1 d D U P A 2
H6'A H 0.0767 0.5301 0.1269 0.043 Uiso 0.1461(13) 1 calc R U P A 2
H6'B H 0.1253 0.6775 0.1562 0.043 Uiso 0.1461(13) 1 calc R U P A 2
C7' C 0.2076(8) 0.388(3) 0.1882(7) 0.039(5) Uiso 0.1461(13) 1 d D U P A 2
H7'A H 0.2262 0.5261 0.1900 0.046 Uiso 0.1461(13) 1 calc R U P A 2
H7'B H 0.2382 0.2863 0.1810 0.046 Uiso 0.1461(13) 1 calc R U P A 2
C8' C 0.1046(9) 0.114(3) 0.1948(7) 0.032(6) Uiso 0.1461(13) 1 d D U P A 2
H8'A H 0.0866 -0.0264 0.1933 0.038 Uiso 0.1461(13) 1 calc R U P A 2
C9' C 0.0837(10) 0.487(3) 0.2087(8) 0.035(7) Uiso 0.1461(13) 1 d D U P A 2
H9'A H 0.0525 0.5884 0.2163 0.042 Uiso 0.1461(13) 1 calc R U P A 2
C10' C 0.1824(9) 0.338(3) 0.2412(8) 0.042(6) Uiso 0.1461(13) 1 d D U P A 2
H10B H 0.2147 0.3431 0.2702 0.050 Uiso 0.1461(13) 1 calc R U P A 2
C11' C 0.0579(10) 0.273(3) 0.2031(11) 0.024(7) Uiso 0.1461(13) 1 d D U P A 2
H11C H 0.0384 0.2379 0.2350 0.029 Uiso 0.1461(13) 1 calc R U P A 2
H11D H 0.0276 0.2701 0.1731 0.029 Uiso 0.1461(13) 1 calc R U P A 2
C12' C 0.1354(11) 0.496(5) 0.2506(11) 0.035(9) Uiso 0.1461(13) 1 d D U P A 2
H12C H 0.1531 0.6349 0.2509 0.042 Uiso 0.1461(13) 1 calc R U P A 2
H12D H 0.1207 0.4714 0.2853 0.042 Uiso 0.1461(13) 1 calc R U P A 2
C13' C 0.1559(13) 0.120(4) 0.2368(12) 0.030(9) Uiso 0.1461(13) 1 d D U P A 2
H13C H 0.1868 0.0215 0.2279 0.036 Uiso 0.1461(13) 1 calc R U P A 2
H13D H 0.1420 0.0790 0.2708 0.036 Uiso 0.1461(13) 1 calc R U P A 2
C14' C 0.1271(10) 0.197(4) -0.0324(9) 0.035(9) Uiso 0.1461(13) 1 d D U P A 2
C15' C 0.0843(8) 0.377(3) -0.0264(7) 0.037(5) Uiso 0.1461(13) 1 d D U P A 2
H15C H 0.0654 0.3621 0.0068 0.044 Uiso 0.1461(13) 1 calc R U P A 2
H15D H 0.1065 0.5084 -0.0249 0.044 Uiso 0.1461(13) 1 calc R U P A 2
C16' C 0.0903(9) -0.002(3) -0.0355(8) 0.035(5) Uiso 0.1461(13) 1 d D U P A 2
H16C H 0.1168 -0.1202 -0.0397 0.042 Uiso 0.1461(13) 1 calc R U P A 2
H16D H 0.0717 -0.0203 -0.0023 0.042 Uiso 0.1461(13) 1 calc R U P A 2
C17' C 0.1534(11) 0.229(6) -0.0846(9) 0.018(8) Uiso 0.1461(13) 1 d D U P A 2
H17C H 0.1748 0.3615 -0.0838 0.022 Uiso 0.1461(13) 1 calc R U P A 2
H17D H 0.1822 0.1181 -0.0895 0.022 Uiso 0.1461(13) 1 calc R U P A 2
C18' C 0.0374(9) 0.382(3) -0.0718(8) 0.033(6) Uiso 0.1461(13) 1 d D U P A 2
H18B H 0.0104 0.5005 -0.0672 0.040 Uiso 0.1461(13) 1 calc R U P A 2
C19' C 0.0423(9) 0.001(3) -0.0806(8) 0.037(7) Uiso 0.1461(13) 1 d D U P A 2
H19B H 0.0197 -0.1313 -0.0818 0.044 Uiso 0.1461(13) 1 calc R U P A 2
C20' C 0.1066(9) 0.229(3) -0.1304(8) 0.046(6) Uiso 0.1461(13) 1 d D U P A 2
H20B H 0.1253 0.2446 -0.1641 0.055 Uiso 0.1461(13) 1 calc R U P A 2
C21' C 0.0009(8) 0.182(3) -0.0740(8) 0.040(5) Uiso 0.1461(13) 1 d D U P A 2
H21C H -0.0190 0.1659 -0.0414 0.048 Uiso 0.1461(13) 1 calc R U P A 2
H21D H -0.0298 0.1873 -0.1037 0.048 Uiso 0.1461(13) 1 calc R U P A 2
C22' C 0.0708(12) 0.032(4) -0.1308(9) 0.025(7) Uiso 0.1461(13) 1 d D U P A 2
H22C H 0.0398 0.0358 -0.1603 0.030 Uiso 0.1461(13) 1 calc R U P A 2
H22D H 0.0970 -0.0864 -0.1365 0.030 Uiso 0.1461(13) 1 calc R U P A 2
C23' C 0.0646(12) 0.406(4) -0.1229(9) 0.044(8) Uiso 0.1461(13) 1 d D U P A 2
H23C H 0.0864 0.5381 -0.1231 0.052 Uiso 0.1461(13) 1 calc R U P A 2
H23D H 0.0331 0.4089 -0.1521 0.052 Uiso 0.1461(13) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.947(4) . ?
C1 C2 1.295(5) . ?
C1 C4 1.502(5) . ?
C2 C3 1.306(5) . ?
C3 C14 1.502(6) . ?
C4 C6 1.537(6) . ?
C4 C7 1.539(6) . ?
C4 C5 1.549(5) . ?
C5 C8 1.536(6) . ?
C6 C9 1.533(6) . ?
C7 C10 1.535(6) . ?
C8 C11 1.531(6) . ?
C8 C13 1.532(5) . ?
C9 C11 1.524(6) . ?
C9 C12 1.534(5) . ?
C10 C12 1.529(6) . ?
C10 C13 1.533(6) . ?
C14 C15 1.530(7) . ?
C14 C17 1.538(6) . ?
C14 C16 1.545(7) . ?
C15 C18 1.526(5) . ?
C16 C19 1.531(6) . ?
C17 C20 1.523(6) . ?
C18 C23 1.519(6) . ?
C18 C21 1.545(6) . ?
C19 C21 1.522(6) . ?
C19 C22 1.525(7) . ?
C20 C22 1.522(6) . ?
C20 C23 1.530(5) . ?
Br1' C1' 1.947(16) . ?
C1' C2' 1.300(16) . ?
C1' C4' 1.506(16) . ?
C2' C3' 1.317(16) . ?
C3' C14' 1.495(17) . ?
C4' C6' 1.527(18) . ?
C4' C7' 1.545(19) . ?
C4' C5' 1.555(17) . ?
C5' C8' 1.569(17) . ?
C6' C9' 1.565(17) . ?
C7' C10' 1.555(18) . ?
C8' C11' 1.510(19) . ?
C8' C13' 1.520(17) . ?
C9' C11' 1.511(19) . ?
C9' C12' 1.526(17) . ?
C10' C12' 1.515(19) . ?
C10' C13' 1.540(19) . ?
C14' C17' 1.524(17) . ?
C14' C15' 1.538(19) . ?
C14' C16' 1.540(19) . ?
C15' C18' 1.514(17) . ?
C16' C19' 1.522(17) . ?
C17' C20' 1.518(18) . ?
C18' C23' 1.504(18) . ?
C18' C21' 1.540(18) . ?
C19' C22' 1.502(19) . ?
C19' C21' 1.528(18) . ?
C20' C22' 1.517(18) . ?
C20' C23' 1.521(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C4 128.2(4) . . ?
C2 C1 Br1 115.7(3) . . ?
C4 C1 Br1 116.1(3) . . ?
C1 C2 C3 179.2(4) . . ?
C2 C3 C14 125.5(4) . . ?
C1 C4 C6 110.5(3) . . ?
C1 C4 C7 111.2(4) . . ?
C6 C4 C7 109.4(3) . . ?
C1 C4 C5 109.0(3) . . ?
C6 C4 C5 108.3(4) . . ?
C7 C4 C5 108.4(3) . . ?
C8 C5 C4 109.8(3) . . ?
C9 C6 C4 110.4(3) . . ?
C10 C7 C4 110.1(3) . . ?
C11 C8 C13 109.2(4) . . ?
C11 C8 C5 110.1(4) . . ?
C13 C8 C5 109.5(4) . . ?
C11 C9 C6 109.7(4) . . ?
C11 C9 C12 108.9(4) . . ?
C6 C9 C12 109.6(4) . . ?
C12 C10 C13 109.5(4) . . ?
C12 C10 C7 109.9(4) . . ?
C13 C10 C7 109.3(3) . . ?
C9 C11 C8 109.6(3) . . ?
C10 C12 C9 109.5(3) . . ?
C8 C13 C10 109.2(3) . . ?
C3 C14 C15 113.3(4) . . ?
C3 C14 C17 109.2(4) . . ?
C15 C14 C17 108.5(4) . . ?
C3 C14 C16 109.5(4) . . ?
C15 C14 C16 108.2(4) . . ?
C17 C14 C16 108.1(4) . . ?
C18 C15 C14 110.9(3) . . ?
C19 C16 C14 110.3(3) . . ?
C20 C17 C14 110.9(4) . . ?
C23 C18 C15 110.4(4) . . ?
C23 C18 C21 108.8(3) . . ?
C15 C18 C21 108.4(4) . . ?
C21 C19 C22 109.9(4) . . ?
C21 C19 C16 108.8(3) . . ?
C22 C19 C16 110.1(4) . . ?
C22 C20 C17 110.1(4) . . ?
C22 C20 C23 109.5(3) . . ?
C17 C20 C23 109.2(3) . . ?
C19 C21 C18 109.7(3) . . ?
C20 C22 C19 109.0(3) . . ?
C18 C23 C20 109.6(3) . . ?
C2' C1' C4' 127.2(16) . . ?
C2' C1' Br1' 115.1(13) . . ?
C4' C1' Br1' 117.3(12) . . ?
C1' C2' C3' 177(2) . . ?
C2' C3' C14' 125.1(18) . . ?
C1' C4' C6' 112.7(17) . . ?
C1' C4' C7' 108.6(17) . . ?
C6' C4' C7' 110.2(15) . . ?
C1' C4' C5' 108.8(14) . . ?
C6' C4' C5' 108.3(16) . . ?
C7' C4' C5' 108.1(15) . . ?
C4' C5' C8' 109.4(13) . . ?
C4' C6' C9' 111.0(14) . . ?
C4' C7' C10' 109.8(13) . . ?
C11' C8' C13' 113(2) . . ?
C11' C8' C5' 107.3(16) . . ?
C13' C8' C5' 107.2(18) . . ?
C11' C9' C12' 111.8(19) . . ?
C11' C9' C6' 105.9(16) . . ?
C12' C9' C6' 107.0(17) . . ?
C12' C10' C13' 111.1(19) . . ?
C12' C10' C7' 108.2(17) . . ?
C13' C10' C7' 107.4(17) . . ?
C8' C11' C9' 111.9(16) . . ?
C10' C12' C9' 112.0(18) . . ?
C8' C13' C10' 110.4(17) . . ?
C3' C14' C17' 109.3(18) . . ?
C3' C14' C15' 112.9(16) . . ?
C17' C14' C15' 106.4(17) . . ?
C3' C14' C16' 112.0(16) . . ?
C17' C14' C16' 108.6(18) . . ?
C15' C14' C16' 107.4(17) . . ?
C18' C15' C14' 110.4(14) . . ?
C19' C16' C14' 112.4(14) . . ?
C20' C17' C14' 112.4(18) . . ?
C23' C18' C15' 111.1(17) . . ?
C23' C18' C21' 108.5(16) . . ?
C15' C18' C21' 110.7(16) . . ?
C22' C19' C16' 108.8(17) . . ?
C22' C19' C21' 107.8(16) . . ?
C16' C19' C21' 109.4(16) . . ?
C22' C20' C17' 110.2(18) . . ?
C22' C20' C23' 107.5(17) . . ?
C17' C20' C23' 107.9(18) . . ?
C19' C21' C18' 108.7(14) . . ?
C19' C22' C20' 112.1(16) . . ?
C18' C23' C20' 109.7(16) . . ?

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.060


####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1485935'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 Br O'
_chemical_formula_sum            'C17 H25 Br O'
_chemical_formula_weight         325.28

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'
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                   10.8427(7)
_cell_length_b                   6.8117(4)
_cell_length_c                   21.2550(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.932(6)
_cell_angle_gamma                90
_cell_volume                     1564.03(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1133
_cell_measurement_theta_min      3.1320
_cell_measurement_theta_max      26.2850

_exptl_crystal_description       plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.620
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            5508
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.142
_diffrn_reflns_theta_max         28.183
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.812
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3118
_reflns_number_gt                1998
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0603P)²+3.1735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3118
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Br1 Br 0.32566(6) 0.75391(9) 0.43332(3) 0.0464(3) Uani 1 1 d . . . . .
O1 O 0.3476(4) 0.7348(7) 0.30193(19) 0.0500(12) Uani 1 1 d . . . . .
C1 C 0.3824(5) 0.6243(9) 0.3592(2) 0.0306(13) Uani 1 1 d . . . . .
C2 C 0.4704(5) 0.7334(9) 0.3265(3) 0.0366(14) Uani 1 1 d . . . . .
C3 C 0.5742(6) 0.8141(9) 0.3135(3) 0.0406(15) Uani 1 1 d . . . . .
H3A H 0.5724 0.8903 0.2760 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3606(5) 0.4057(8) 0.3565(2) 0.0298(12) Uani 1 1 d . . . . .
C5 C 0.4169(6) 0.3191(11) 0.2989(3) 0.0476(17) Uani 1 1 d . . . . .
H5A H 0.5071 0.3343 0.3040 0.071 Uiso 1 1 calc R U . . .
H5B H 0.3836 0.3882 0.2607 0.071 Uiso 1 1 calc R U . . .
H5C H 0.3960 0.1794 0.2952 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4240(6) 0.3092(8) 0.4161(3) 0.0386(14) Uani 1 1 d . . . . .
H6A H 0.4125 0.1667 0.4136 0.058 Uiso 1 1 calc R U . . .
H6B H 0.3873 0.3598 0.4534 0.058 Uiso 1 1 calc R U . . .
H6C H 0.5126 0.3397 0.4193 0.058 Uiso 1 1 calc R U . . .
C7 C 0.2210(5) 0.3643(10) 0.3523(3) 0.0412(15) Uani 1 1 d . . . . .
H7A H 0.1805 0.4312 0.3153 0.062 Uiso 1 1 calc R U . . .
H7B H 0.1866 0.4127 0.3905 0.062 Uiso 1 1 calc R U . . .
H7C H 0.2067 0.2226 0.3484 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6968(5) 0.7979(8) 0.3522(2) 0.0275(12) Uani 1 1 d . . . . .
C9 C 0.6955(5) 0.6449(8) 0.4040(2) 0.0280(12) Uani 1 1 d . . . . .
H9A H 0.6777 0.5142 0.3849 0.034 Uiso 1 1 calc R U . . .
H9B H 0.6291 0.6763 0.4316 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7994(5) 0.7441(9) 0.3099(2) 0.0338(13) Uani 1 1 d . . . . .
H10A H 0.7813 0.6146 0.2900 0.041 Uiso 1 1 calc R U . . .
H10B H 0.8023 0.8428 0.2759 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7298(5) 1.0031(9) 0.3820(3) 0.0373(14) Uani 1 1 d . . . . .
H11A H 0.7335 1.1023 0.3481 0.045 Uiso 1 1 calc R U . . .
H11B H 0.6650 1.0436 0.4094 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8205(5) 0.6392(9) 0.4436(3) 0.0342(14) Uani 1 1 d . . . . .
H12A H 0.8174 0.5394 0.4779 0.041 Uiso 1 1 calc R U . . .
C13 C 0.9249(5) 0.7366(9) 0.3488(3) 0.0366(14) Uani 1 1 d . . . . .
H13A H 0.9903 0.6994 0.3206 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8538(6) 0.9922(9) 0.4206(3) 0.0409(15) Uani 1 1 d . . . . .
H14A H 0.8734 1.1233 0.4401 0.049 Uiso 1 1 calc R U . . .
C15 C 0.9212(5) 0.5831(9) 0.4011(3) 0.0382(14) Uani 1 1 d . . . . .
H15A H 0.9034 0.4520 0.3823 0.046 Uiso 1 1 calc R U . . .
H15B H 1.0024 0.5773 0.4261 0.046 Uiso 1 1 calc R U . . .
C16 C 0.9557(6) 0.9369(9) 0.3778(3) 0.0436(16) Uani 1 1 d . . . . .
H16A H 0.9599 1.0362 0.3440 0.052 Uiso 1 1 calc R U . . .
H16B H 1.0370 0.9322 0.4027 0.052 Uiso 1 1 calc R U . . .
C17 C 0.8498(6) 0.8390(10) 0.4726(3) 0.0408(15) Uani 1 1 d . . . . .
H17A H 0.9308 0.8343 0.4979 0.049 Uiso 1 1 calc R U . . .
H17B H 0.7858 0.8751 0.5010 0.049 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
Br1 C1 1.951(5) . ?
O1 C2 1.388(7) . ?
O1 C1 1.453(6) . ?
C1 C2 1.435(8) . ?
C1 C4 1.508(8) . ?
C2 C3 1.304(8) . ?
C3 C8 1.505(8) . ?
C4 C5 1.532(7) . ?
C4 C7 1.535(7) . ?
C4 C6 1.535(8) . ?
C8 C9 1.517(7) . ?
C8 C10 1.534(7) . ?
C8 C11 1.564(8) . ?
C9 C12 1.534(7) . ?
C10 C13 1.531(8) . ?
C11 C14 1.515(8) . ?
C12 C17 1.516(9) . ?
C12 C15 1.524(8) . ?
C13 C16 1.522(8) . ?
C13 C15 1.529(8) . ?
C14 C17 1.524(8) . ?
C14 C16 1.537(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 60.6(3) . . ?
C2 C1 O1 57.4(3) . . ?
C2 C1 C4 127.0(5) . . ?
O1 C1 C4 116.8(4) . . ?
C2 C1 Br1 115.2(4) . . ?
O1 C1 Br1 111.4(4) . . ?
C4 C1 Br1 114.7(4) . . ?
C3 C2 O1 137.3(5) . . ?
C3 C2 C1 160.6(6) . . ?
O1 C2 C1 61.9(4) . . ?
C2 C3 C8 126.2(5) . . ?
C1 C4 C5 109.8(5) . . ?
C1 C4 C7 109.5(5) . . ?
C5 C4 C7 110.0(4) . . ?
C1 C4 C6 109.5(4) . . ?
C5 C4 C6 108.2(5) . . ?
C7 C4 C6 109.8(5) . . ?
C3 C8 C9 112.6(4) . . ?
C3 C8 C10 110.4(4) . . ?
C9 C8 C10 108.3(4) . . ?
C3 C8 C11 108.5(5) . . ?
C9 C8 C11 109.6(4) . . ?
C10 C8 C11 107.3(4) . . ?
C8 C9 C12 110.7(4) . . ?
C13 C10 C8 110.3(4) . . ?
C14 C11 C8 109.7(5) . . ?
C17 C12 C15 109.3(5) . . ?
C17 C12 C9 110.2(5) . . ?
C15 C12 C9 109.0(5) . . ?
C16 C13 C15 109.7(5) . . ?
C16 C13 C10 110.0(5) . . ?
C15 C13 C10 109.8(5) . . ?
C11 C14 C17 110.3(5) . . ?
C11 C14 C16 109.9(5) . . ?
C17 C14 C16 109.2(5) . . ?
C12 C15 C13 108.9(5) . . ?
C13 C16 C14 108.4(5) . . ?
C12 C17 C14 109.7(4) . . ?

_refine_diff_density_max         0.952
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.098



#===END


