# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_120927a_0m
_database_code_depnum_ccdc_archive 'CCDC 1439964'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
(S)-7-((R)-1-(4-bromophenyl)prop-2-yn-1-yl)-1,4-dioxaspiro[4.5]decan-8-one

_chemical_name_common            (S,R)-3p

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C17 H17 Br O3'

_chemical_formula_weight         349.22



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'



_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P21/c



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   5.776(3)

_cell_length_b                   32.024(16)

_cell_length_c                   9.608(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 115.031(13)

_cell_angle_gamma                90.00

_cell_volume                     1610.3(13)

_cell_formula_units_Z            4

_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    4266

_cell_measurement_theta_min      2.43

_cell_measurement_theta_max      25.94



_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.15

_exptl_crystal_size_mid          0.13

_exptl_crystal_size_min          0.12

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.440

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    2.559

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7001

_exptl_absorpt_correction_T_max  0.7487

_exptl_absorpt_process_details   ?



_exptl_special_details           
;

 ?

;



_diffrn_ambient_temperature      293(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            13713

_diffrn_reflns_av_R_equivalents  0.0563

_diffrn_reflns_av_sigmaI/netI    0.0628

_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -41

_diffrn_reflns_limit_k_max       41

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.42

_diffrn_reflns_theta_max         27.80

_reflns_number_total             3749

_reflns_number_gt                2117

_reflns_threshold_expression     >2sigma(I)



_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'



_refine_special_details          
;

 Refinement of F² against ALL reflections.  The weighted R-factor wR and

 goodness of fit S are based on F², conventional R-factors R are based

 on F, with F set to zero for negative F². The threshold expression of

 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

 not relevant to the choice of reflections for refinement.  R-factors based

 on F² are statistically about twice as large as those based on F, and R-

 factors based on ALL data will be even larger.

;



_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1548P)²+1.6234P] 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         3749

_refine_ls_number_parameters     190

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1427

_refine_ls_R_factor_gt           0.0938

_refine_ls_wR_factor_ref         0.2839

_refine_ls_wR_factor_gt          0.2529

_refine_ls_goodness_of_fit_ref   1.066

_refine_ls_restrained_S_all      1.066

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group






































Br1 Br 0.0975(2) -0.03450(2) 1.27342(11) 0.0920(5) Uani 1 1 d . . .
C1 C 0.1366(9) 0.15333(16) 0.7082(6) 0.0370(11) Uani 1 1 d . . .
C2 C 0.0637(12) 0.19855(19) 0.6659(7) 0.0518(15) Uani 1 1 d . . .
H2A H 0.2055 0.2164 0.7282 0.062 Uiso 1 1 calc R . .
H2B H 0.0295 0.2029 0.5591 0.062 Uiso 1 1 calc R . .
C3 C -0.1700(12) 0.2106(2) 0.6902(7) 0.0538(15) Uani 1 1 d . . .
H3A H -0.1978 0.2404 0.6742 0.065 Uiso 1 1 calc R . .
H3B H -0.3180 0.1965 0.6141 0.065 Uiso 1 1 calc R . .
C4 C -0.1479(10) 0.19980(16) 0.8470(6) 0.0403(12) Uani 1 1 d . . .
C5 C -0.0440(9) 0.15664(15) 0.9066(5) 0.0340(11) Uani 1 1 d . . .
H5 H -0.1803 0.1368 0.8494 0.041 Uiso 1 1 calc R . .
C6 C 0.1825(9) 0.14527(17) 0.8724(6) 0.0383(11) Uani 1 1 d . . .
H6A H 0.3301 0.1612 0.9397 0.046 Uiso 1 1 calc R . .
H6B H 0.2218 0.1159 0.8952 0.046 Uiso 1 1 calc R . .
C7 C 0.0124(13) 0.1152(2) 0.4895(7) 0.0600(17) Uani 1 1 d . . .
H7A H -0.0595 0.1349 0.4054 0.072 Uiso 1 1 calc R . .
H7B H -0.0459 0.0873 0.4511 0.072 Uiso 1 1 calc R . .
C8 C 0.2929(13) 0.1173(3) 0.5611(9) 0.075(2) Uani 1 1 d . . .
H8A H 0.3657 0.0897 0.5907 0.090 Uiso 1 1 calc R . .
H8B H 0.3547 0.1292 0.4902 0.090 Uiso 1 1 calc R . .
C9 C 0.0131(10) 0.15128(16) 1.0781(6) 0.0393(12) Uani 1 1 d . . .
H9 H -0.1379 0.1615 1.0894 0.047 Uiso 1 1 calc R . .
C10 C 0.0427(10) 0.10561(15) 1.1247(5) 0.0337(11) Uani 1 1 d . . .
C11 C -0.1747(11) 0.08049(19) 1.0804(7) 0.0515(14) Uani 1 1 d . . .
H11 H -0.3343 0.0918 1.0202 0.062 Uiso 1 1 calc R . .
C12 C -0.1566(14) 0.0393(2) 1.1244(9) 0.0628(18) Uani 1 1 d . . .
H12 H -0.3039 0.0232 1.0952 0.075 Uiso 1 1 calc R . .
C13 C 0.0757(14) 0.02180(19) 1.2105(8) 0.0546(15) Uani 1 1 d . . .
C14 C 0.2945(13) 0.04557(19) 1.2535(8) 0.0563(16) Uani 1 1 d . . .
H14 H 0.4536 0.0337 1.3115 0.068 Uiso 1 1 calc R . .
C15 C 0.2757(11) 0.08738(18) 1.2097(6) 0.0455(13) Uani 1 1 d . . .
H15 H 0.4236 0.1033 1.2386 0.055 Uiso 1 1 calc R . .
C16 C 0.2263(12) 0.17733(17) 1.1770(6) 0.0462(13) Uani 1 1 d . . .
C17 C 0.4020(14) 0.1975(2) 1.2541(7) 0.0653(19) Uani 1 1 d . . .
H17 H 0.5420 0.2137 1.3155 0.078 Uiso 1 1 calc R . .
O1 O -0.0567(7) 0.12580(12) 0.6115(4) 0.0435(9) Uani 1 1 d . . .
O2 O 0.3594(7) 0.14251(16) 0.6890(4) 0.0528(11) Uani 1 1 d . . .
O3 O -0.2244(9) 0.22268(14) 0.9185(5) 0.0603(12) Uani 1 1 d . . .






_geom_special_details            
;

 All esds (except the esd in the dihedral angle between two l.s. planes)

 are estimated using the full covariance matrix.  The cell esds are taken

 into account individually in the estimation of esds in distances, angles

 and torsion angles; correlations between esds in cell parameters are only

 used when they are defined by crystal symmetry.  An approximate (isotropic)

 treatment of cell esds is used for estimating esds involving l.s. planes.

;



loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag








































Br1 C13 1.889(6) . ?
C1 O1 1.417(6) . ?
C1 O2 1.418(6) . ?
C1 C6 1.507(7) . ?
C1 C2 1.515(8) . ?
C2 C3 1.513(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.497(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.209(7) . ?
C4 C5 1.519(7) . ?
C5 C6 1.522(7) . ?
C5 C9 1.547(7) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O1 1.430(7) . ?
C7 C8 1.470(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.381(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C16 1.458(8) . ?
C9 C10 1.518(7) . ?
C9 H9 0.9800 . ?
C10 C15 1.374(7) . ?
C10 C11 1.398(8) . ?
C11 C12 1.376(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(10) . ?
C14 C15 1.394(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.167(9) . ?
C17 H17 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









































































O1 C1 O2 105.6(4) . . ?
O1 C1 C6 108.7(4) . . ?
O2 C1 C6 109.1(4) . . ?
O1 C1 C2 111.5(4) . . ?
O2 C1 C2 111.3(4) . . ?
C6 C1 C2 110.5(4) . . ?
C3 C2 C1 111.5(5) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 113.3(5) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O3 C4 C3 122.4(5) . . ?
O3 C4 C5 121.2(5) . . ?
C3 C4 C5 116.2(5) . . ?
C4 C5 C6 112.0(4) . . ?
C4 C5 C9 112.0(4) . . ?
C6 C5 C9 112.8(4) . . ?
C4 C5 H5 106.5 . . ?
C6 C5 H5 106.5 . . ?
C9 C5 H5 106.5 . . ?
C1 C6 C5 113.5(4) . . ?
C1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 C8 103.8(5) . . ?
O1 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
O1 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
O2 C8 C7 106.3(5) . . ?
O2 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
O2 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C16 C9 C10 113.6(4) . . ?
C16 C9 C5 111.8(4) . . ?
C10 C9 C5 111.6(4) . . ?
C16 C9 H9 106.4 . . ?
C10 C9 H9 106.4 . . ?
C5 C9 H9 106.4 . . ?
C15 C10 C11 117.7(5) . . ?
C15 C10 C9 123.0(5) . . ?
C11 C10 C9 119.4(5) . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 120.5(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.8(6) . . ?
C12 C13 Br1 120.1(5) . . ?
C14 C13 Br1 120.1(5) . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 121.3(6) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C9 177.7(7) . . ?
C16 C17 H17 180.0 . . ?
C1 O1 C7 105.6(4) . . ?
C8 O2 C1 109.4(4) . . ?



loop_

_geom_torsion_atom_site_label_1

_geom_torsion_atom_site_label_2

_geom_torsion_atom_site_label_3

_geom_torsion_atom_site_label_4

_geom_torsion

_geom_torsion_site_symmetry_1

_geom_torsion_site_symmetry_2

_geom_torsion_site_symmetry_3

_geom_torsion_site_symmetry_4

_geom_torsion_publ_flag












































O1 C1 C2 C3 63.8(6) . . . . ?
O2 C1 C2 C3 -178.5(5) . . . . ?
C6 C1 C2 C3 -57.1(6) . . . . ?
C1 C2 C3 C4 51.7(7) . . . . ?
C2 C3 C4 O3 140.0(6) . . . . ?
C2 C3 C4 C5 -45.0(7) . . . . ?
O3 C4 C5 C6 -142.4(5) . . . . ?
C3 C4 C5 C6 42.6(6) . . . . ?
O3 C4 C5 C9 -14.4(7) . . . . ?
C3 C4 C5 C9 170.6(5) . . . . ?
O1 C1 C6 C5 -66.4(5) . . . . ?
O2 C1 C6 C5 178.9(4) . . . . ?
C2 C1 C6 C5 56.2(6) . . . . ?
C4 C5 C6 C1 -48.2(6) . . . . ?
C9 C5 C6 C1 -175.7(4) . . . . ?
O1 C7 C8 O2 -21.6(8) . . . . ?
C4 C5 C9 C16 -67.9(6) . . . . ?
C6 C5 C9 C16 59.6(6) . . . . ?
C4 C5 C9 C10 163.6(4) . . . . ?
C6 C5 C9 C10 -68.8(6) . . . . ?
C16 C9 C10 C15 -23.1(7) . . . . ?
C5 C9 C10 C15 104.4(6) . . . . ?
C16 C9 C10 C11 156.8(5) . . . . ?
C5 C9 C10 C11 -75.7(6) . . . . ?
C15 C10 C11 C12 1.9(9) . . . . ?
C9 C10 C11 C12 -178.0(6) . . . . ?
C10 C11 C12 C13 -1.1(11) . . . . ?
C11 C12 C13 C14 -0.1(11) . . . . ?
C11 C12 C13 Br1 178.8(5) . . . . ?
C12 C13 C14 C15 0.6(10) . . . . ?
Br1 C13 C14 C15 -178.4(5) . . . . ?
C11 C10 C15 C14 -1.5(8) . . . . ?
C9 C10 C15 C14 178.4(5) . . . . ?
C13 C14 C15 C10 0.3(10) . . . . ?
C10 C9 C16 C17 71(16) . . . . ?
C5 C9 C16 C17 -56(16) . . . . ?
O2 C1 O1 C7 -27.8(6) . . . . ?
C6 C1 O1 C7 -144.7(5) . . . . ?
C2 C1 O1 C7 93.3(5) . . . . ?
C8 C7 O1 C1 30.3(7) . . . . ?
C7 C8 O2 C1 4.8(8) . . . . ?
O1 C1 O2 C8 14.1(7) . . . . ?
C6 C1 O2 C8 130.8(6) . . . . ?
C2 C1 O2 C8 -107.1(6) . . . . ?



_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        27.80

_diffrn_measured_fraction_theta_full 0.980

_refine_diff_density_max         1.971

_refine_diff_density_min         -0.539

_refine_diff_density_rms         0.137

