# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_x2266fin
_database_code_depnum_ccdc_archive 'CCDC 1412686'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-08-14 downloaded from the CCDC.
;

_audit_creation_date             2015-05-20T13:19:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H21 Br O3'
_chemical_formula_weight         365.26
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2717(2)
_cell_length_b                   5.63430(10)
_cell_length_c                   15.8631(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.448(2)
_cell_angle_gamma                90
_cell_volume                     814.94(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5102
_cell_measurement_theta_min      2.227
_cell_measurement_theta_max      30.629

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             376

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_type   multi-scan
_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)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.80872
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0191587
_diffrn_orient_matrix_ub_12      -0.0081677
_diffrn_orient_matrix_ub_13      0.0412404
_diffrn_orient_matrix_ub_21      -0.0738926
_diffrn_orient_matrix_ub_22      -0.0229873
_diffrn_orient_matrix_ub_23      -0.0191615
_diffrn_orient_matrix_ub_31      0.0149829
_diffrn_orient_matrix_ub_32      -0.1234383
_diffrn_orient_matrix_ub_33      0.0008524
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_number            13344
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         32.343
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.917
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.891
_reflns_Friedel_coverage         0.795
_reflns_number_total             5337
_reflns_number_gt                4523
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
;
 SHELXS-2013
 Program for Crystal Structure Analysis (Release 2013-1)
 G. M. Sheldrick, Institüt für Anorganische Chemie der Universität,
 Tammanstrasse 4, D-3400 Göttingen, Germany.
 G. M. Sheldrick, Acta. Cryst., 2008, A64, 112 - 122
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
;
_computing_publication_material  
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+0.2232P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5337
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(4)
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.68
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.63914(3) 0.60047(6) 0.50171(2) 0.04441(9) Uani 1 1 d . . . . .
O1 O 1.3557(2) 0.4264(4) 0.05250(12) 0.0313(4) Uani 1 1 d . . . . .
O2 O 1.6010(2) 0.4754(4) 0.09450(13) 0.0338(4) Uani 1 1 d . . . . .
O3 O 1.1942(3) 0.0060(4) 0.01311(14) 0.0344(4) Uani 1 1 d . . . . .
C1 C 1.1838(3) 0.5058(5) 0.14346(16) 0.0273(5) Uani 1 1 d . . . . .
C2 C 1.2204(3) 0.3965(5) 0.07629(16) 0.0267(5) Uani 1 1 d . . . . .
C3 C 1.4650(3) 0.5671(5) 0.10539(17) 0.0306(6) Uani 1 1 d . . . . .
C4 C 1.6301(3) 0.2412(5) 0.12937(19) 0.0340(6) Uani 1 1 d . . . . .
C5 C 1.6289(3) 0.2401(6) 0.22447(19) 0.0351(6) Uani 1 1 d . . . . .
C6 C 1.4815(3) 0.3305(5) 0.24150(18) 0.0316(6) Uani 1 1 d . . . . .
C7 C 1.4467(3) 0.5727(6) 0.19926(16) 0.0302(5) Uani 1 1 d . . . . .
C8 C 1.2909(3) 0.6642(5) 0.20011(18) 0.0315(6) Uani 1 1 d . . . . .
C9 C 1.2370(3) 0.6666(5) 0.28714(18) 0.0354(7) Uani 1 1 d . . . . .
C10 C 1.1186(3) 0.4727(5) 0.28065(16) 0.0272(5) Uani 1 1 d . . . . .
C11 C 1.0523(3) 0.4649(6) 0.18399(17) 0.0305(5) Uani 1 1 d . . . . .
C12 C 1.1284(3) 0.2321(6) 0.01531(18) 0.0307(6) Uani 1 1 d . . . . .
C13 C 1.0059(3) 0.5086(5) 0.33699(15) 0.0253(5) Uani 1 1 d . . . . .
C14 C 0.9810(3) 0.3350(5) 0.39520(16) 0.0272(5) Uani 1 1 d . . . . .
C15 C 0.8740(3) 0.3597(5) 0.44511(17) 0.0290(5) Uani 1 1 d . . . . .
C16 C 0.7891(3) 0.5620(5) 0.43585(15) 0.0284(6) Uani 1 1 d . . . . .
C17 C 0.8108(3) 0.7400(5) 0.37925(17) 0.0293(5) Uani 1 1 d . . . . .
C18 C 0.9184(3) 0.7114(5) 0.33013(17) 0.0301(5) Uani 1 1 d . . . . .
H1O3 H 1.263(5) 0.015(7) -0.011(3) 0.057(13) Uiso 1 1 d . . . . .
H3 H 1.457(4) 0.730(6) 0.079(2) 0.031(9) Uiso 1 1 d . . . . .
H4A H 1.561(3) 0.131(7) 0.0996(18) 0.033(8) Uiso 1 1 d . . . . .
H4E H 1.722(4) 0.197(6) 0.118(2) 0.034(9) Uiso 1 1 d . . . . .
H5A H 1.708(4) 0.332(7) 0.254(2) 0.046(10) Uiso 1 1 d . . . . .
H5E H 1.649(3) 0.077(8) 0.2466(19) 0.034(8) Uiso 1 1 d . . . . .
H6A H 1.404(4) 0.211(6) 0.218(2) 0.034(8) Uiso 1 1 d . . . . .
H6E H 1.481(3) 0.347(6) 0.300(2) 0.027(8) Uiso 1 1 d . . . . .
H7 H 1.517(4) 0.682(6) 0.227(2) 0.040(10) Uiso 1 1 d . . . . .
H8 H 1.286(4) 0.830(6) 0.178(2) 0.035(9) Uiso 1 1 d . . . . .
H9A H 1.193(4) 0.831(7) 0.297(2) 0.038(10) Uiso 1 1 d . . . . .
H9B H 1.315(3) 0.639(7) 0.334(2) 0.039(9) Uiso 1 1 d . . . . .
H10 H 1.165(4) 0.316(6) 0.294(2) 0.030(9) Uiso 1 1 d . . . . .
H11A H 0.979(3) 0.582(8) 0.1705(17) 0.031(7) Uiso 1 1 d . . . . .
H11B H 1.007(4) 0.302(7) 0.168(2) 0.044(10) Uiso 1 1 d . . . . .
H12A H 1.118(4) 0.299(7) -0.045(2) 0.046(10) Uiso 1 1 d . . . . .
H12B H 1.031(3) 0.201(5) 0.0303(19) 0.025(8) Uiso 1 1 d . . . . .
H14 H 1.035(4) 0.195(6) 0.398(2) 0.035(9) Uiso 1 1 d . . . . .
H15 H 0.854(3) 0.245(7) 0.486(2) 0.037(9) Uiso 1 1 d . . . . .
H17 H 0.756(4) 0.876(7) 0.374(2) 0.035(9) Uiso 1 1 d . . . . .
H18 H 0.931(4) 0.845(8) 0.291(2) 0.052(11) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C16 1.897(2) . ?
O1 C2 1.384(3) . ?
O1 C3 1.432(3) . ?
O2 C3 1.402(3) . ?
O2 C4 1.437(4) . ?
O3 C12 1.415(3) . ?
O3 H1O3 0.80(4) . ?
C1 C2 1.327(4) . ?
C1 C11 1.496(4) . ?
C1 C8 1.505(4) . ?
C2 C12 1.491(4) . ?
C3 C7 1.529(4) . ?
C3 H3 1.01(3) . ?
C4 C5 1.510(4) . ?
C4 H4A 0.96(3) . ?
C4 H4E 0.94(3) . ?
C5 C6 1.527(4) . ?
C5 H5A 0.95(4) . ?
C5 H5E 0.99(4) . ?
C6 C7 1.529(4) . ?
C6 H6A 1.00(3) . ?
C6 H6E 0.93(3) . ?
C7 C8 1.536(4) . ?
C7 H7 0.95(3) . ?
C8 C9 1.551(4) . ?
C8 H8 0.99(4) . ?
C9 C10 1.539(4) . ?
C9 H9A 1.04(4) . ?
C9 H9B 0.95(3) . ?
C10 C13 1.507(4) . ?
C10 C11 1.546(4) . ?
C10 H10 0.98(4) . ?
C11 H11A 0.94(4) . ?
C11 H11B 1.02(4) . ?
C12 H12A 1.02(4) . ?
C12 H12B 0.99(3) . ?
C13 C14 1.393(4) . ?
C13 C18 1.395(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.93(3) . ?
C15 C16 1.378(4) . ?
C15 H15 0.96(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.91(4) . ?
C18 H18 1.00(4) . ?

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 C3 119.2(2) . . ?
C3 O2 C4 113.6(2) . . ?
C12 O3 H1O3 110(3) . . ?
C2 C1 C11 128.4(2) . . ?
C2 C1 C8 121.1(2) . . ?
C11 C1 C8 109.6(2) . . ?
C1 C2 O1 122.6(2) . . ?
C1 C2 C12 127.6(3) . . ?
O1 C2 C12 109.8(2) . . ?
O2 C3 O1 106.3(2) . . ?
O2 C3 C7 112.9(2) . . ?
O1 C3 C7 113.0(2) . . ?
O2 C3 H3 106.6(19) . . ?
O1 C3 H3 106(2) . . ?
C7 C3 H3 112.0(19) . . ?
O2 C4 C5 110.7(2) . . ?
O2 C4 H4A 110(2) . . ?
C5 C4 H4A 111.4(18) . . ?
O2 C4 H4E 106(2) . . ?
C5 C4 H4E 111(2) . . ?
H4A C4 H4E 107(3) . . ?
C4 C5 C6 110.1(2) . . ?
C4 C5 H5A 110(2) . . ?
C6 C5 H5A 112(2) . . ?
C4 C5 H5E 108.9(18) . . ?
C6 C5 H5E 111.3(17) . . ?
H5A C5 H5E 105(3) . . ?
C5 C6 C7 110.2(2) . . ?
C5 C6 H6A 108.1(19) . . ?
C7 C6 H6A 111.0(19) . . ?
C5 C6 H6E 112(2) . . ?
C7 C6 H6E 108(2) . . ?
H6A C6 H6E 108(3) . . ?
C6 C7 C3 110.9(2) . . ?
C6 C7 C8 114.8(2) . . ?
C3 C7 C8 106.6(2) . . ?
C6 C7 H7 108(2) . . ?
C3 C7 H7 106(2) . . ?
C8 C7 H7 110(2) . . ?
C1 C8 C7 108.4(2) . . ?
C1 C8 C9 104.6(2) . . ?
C7 C8 C9 117.8(2) . . ?
C1 C8 H8 111.3(19) . . ?
C7 C8 H8 107.4(19) . . ?
C9 C8 H8 107(2) . . ?
C10 C9 C8 106.0(2) . . ?
C10 C9 H9A 110(2) . . ?
C8 C9 H9A 110(2) . . ?
C10 C9 H9B 112(2) . . ?
C8 C9 H9B 111.6(19) . . ?
H9A C9 H9B 107(3) . . ?
C13 C10 C9 115.3(2) . . ?
C13 C10 C11 113.5(2) . . ?
C9 C10 C11 103.7(2) . . ?
C13 C10 H10 109(2) . . ?
C9 C10 H10 110(2) . . ?
C11 C10 H10 105(2) . . ?
C1 C11 C10 102.3(2) . . ?
C1 C11 H11A 113.8(19) . . ?
C10 C11 H11A 110.2(17) . . ?
C1 C11 H11B 111(2) . . ?
C10 C11 H11B 110(2) . . ?
H11A C11 H11B 109(3) . . ?
O3 C12 C2 112.2(2) . . ?
O3 C12 H12A 106(2) . . ?
C2 C12 H12A 109(2) . . ?
O3 C12 H12B 105.1(17) . . ?
C2 C12 H12B 113.2(17) . . ?
H12A C12 H12B 111(3) . . ?
C14 C13 C18 117.6(2) . . ?
C14 C13 C10 121.0(2) . . ?
C18 C13 C10 121.3(2) . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 H14 120(2) . . ?
C13 C14 H14 118(2) . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 117(2) . . ?
C14 C15 H15 125(2) . . ?
C15 C16 C17 121.4(2) . . ?
C15 C16 Br1 119.8(2) . . ?
C17 C16 Br1 118.8(2) . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 119(2) . . ?
C16 C17 H17 122(2) . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 116(2) . . ?
C13 C18 H18 122(2) . . ?

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
O3 H1O3 O2 0.80(4) 2.00(4) 2.780(3) 163(4) 2_845

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
