# 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. 
# 
#######################################################################

data_cd16282
_database_code_depnum_ccdc_archive 'CCDC 1537514'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(S)-4-(1-(4-bromophenyl)prop-2-yn-1-yl)-3,4,5-trimethoxycyclohexa-2,5-dienone
_chemical_name_common            (S)-3fa
_chemical_melting_point          162-164
_chemical_formula_moiety         C18H17BrO4
_chemical_formula_sum            'C18 H17 Br O4'
_chemical_formula_weight         377.23

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'
O O 0.0106 0.0060 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.6645(15)
_cell_length_b                   13.511(3)
_cell_length_c                   8.2107(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.474(4)
_cell_angle_gamma                90
_cell_volume                     841.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1648
_cell_measurement_theta_min      5.016
_cell_measurement_theta_max      44.533

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.461
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5857
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5027
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3090
_reflns_number_gt                2629
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.876

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0143P)²] 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_abs_structure_details 
; 
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.007(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.984
_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 1.24344(8) 0.54920(5) 1.05146(6) 0.0686(2) Uani 1 1 d . . . . .
O1 O 0.9075(5) 0.5303(3) 0.3386(5) 0.0656(12) Uani 1 1 d . . . . .
O2 O 0.4298(4) 0.6877(2) 0.5338(4) 0.0422(8) Uani 1 1 d . . . . .
O3 O 0.8899(5) 0.8781(2) 0.3783(5) 0.0510(9) Uani 1 1 d . . . . .
O4 O 0.5410(4) 0.8534(2) 0.3880(4) 0.0402(8) Uani 1 1 d . . . . .
C1 C 0.5869(6) 0.6835(3) 0.4803(5) 0.0340(10) Uani 1 1 d . . . . .
C2 C 0.6670(7) 0.6019(4) 0.4403(6) 0.0405(11) Uani 1 1 d . . . . .
H2 H 0.6152 0.5408 0.4536 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8341(7) 0.6057(4) 0.3761(6) 0.0442(12) Uani 1 1 d . . . . .
C4 C 0.9086(7) 0.7024(4) 0.3534(6) 0.0441(12) Uani 1 1 d . . . . .
H4 H 1.0128 0.7065 0.3083 0.053 Uiso 1 1 calc R U . . .
C5 C 0.8334(6) 0.7854(3) 0.3944(5) 0.0374(11) Uani 1 1 d . . . . .
C6 C 0.6640(6) 0.7864(3) 0.4723(5) 0.0306(10) Uani 1 1 d . . . . .
C7 C 0.7128(6) 0.8331(3) 0.6513(5) 0.0300(10) Uani 1 1 d . . . . .
H7 H 0.7772 0.8945 0.6378 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5575(6) 0.8607(3) 0.7227(6) 0.0358(11) Uani 1 1 d . . . . .
C9 C 0.4391(7) 0.8920(4) 0.7839(6) 0.0427(12) Uani 1 1 d . . . . .
H9 H 0.3457 0.9167 0.8322 0.051 Uiso 1 1 calc R U . . .
C10 C 0.8391(6) 0.7661(3) 0.7618(5) 0.0320(10) Uani 1 1 d . . . . .
C11 C 0.7827(7) 0.6888(4) 0.8511(5) 0.0408(11) Uani 1 1 d . . . . .
H11 H 0.6624 0.6794 0.8508 0.049 Uiso 1 1 calc R U . . .
C12 C 0.9003(7) 0.6255(4) 0.9403(6) 0.0431(12) Uani 1 1 d . . . . .
H12 H 0.8607 0.5737 0.9997 0.052 Uiso 1 1 calc R U . . .
C13 C 1.0782(7) 0.6403(4) 0.9403(6) 0.0436(12) Uani 1 1 d . . . . .
C14 C 1.1388(7) 0.7170(4) 0.8584(6) 0.0452(13) Uani 1 1 d . . . . .
H14 H 1.2593 0.7270 0.8618 0.054 Uiso 1 1 calc R U . . .
C15 C 1.0185(7) 0.7803(4) 0.7694(6) 0.0435(12) Uani 1 1 d . . . . .
H15 H 1.0594 0.8334 0.7136 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3397(8) 0.5958(4) 0.5476(7) 0.0538(14) Uani 1 1 d . . . . .
H16A H 0.3248 0.5623 0.4434 0.081 Uiso 1 1 calc R U . . .
H16B H 0.2262 0.6085 0.5794 0.081 Uiso 1 1 calc R U . . .
H16C H 0.4078 0.5551 0.6293 0.081 Uiso 1 1 calc R U . . .
C17 C 1.0536(8) 0.8906(5) 0.3145(8) 0.0669(17) Uani 1 1 d . . . . .
H17A H 1.1473 0.8598 0.3877 0.100 Uiso 1 1 calc R U . . .
H17B H 1.0782 0.9599 0.3056 0.100 Uiso 1 1 calc R U . . .
H17C H 1.0446 0.8604 0.2078 0.100 Uiso 1 1 calc R U . . .
C18 C 0.4906(9) 0.8318(5) 0.2182(6) 0.0633(16) Uani 1 1 d . . . . .
H18A H 0.5908 0.8391 0.1615 0.095 Uiso 1 1 calc R U . . .
H18B H 0.3992 0.8766 0.1722 0.095 Uiso 1 1 calc R U . . .
H18C H 0.4478 0.7650 0.2063 0.095 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 C13 1.901(5) . ?
O1 C3 1.225(6) . ?
O2 C1 1.342(5) . ?
O2 C16 1.433(5) . ?
O3 C5 1.338(5) . ?
O3 C17 1.439(6) . ?
O4 C6 1.412(5) . ?
O4 C18 1.421(6) . ?
C1 C2 1.327(6) . ?
C1 C6 1.516(6) . ?
C2 C3 1.456(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.449(8) . ?
C4 C5 1.327(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.530(7) . ?
C6 C7 1.592(6) . ?
C7 C8 1.451(7) . ?
C7 C10 1.523(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.178(6) . ?
C9 H9 0.9300 . ?
C10 C15 1.381(7) . ?
C10 C11 1.382(6) . ?
C11 C12 1.373(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.354(7) . ?
C14 C15 1.384(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 O2 C16 117.1(4) . . ?
C5 O3 C17 117.2(4) . . ?
C6 O4 C18 114.5(4) . . ?
C2 C1 O2 125.9(4) . . ?
C2 C1 C6 123.6(4) . . ?
O2 C1 C6 110.5(4) . . ?
C1 C2 C3 121.7(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
O1 C3 C4 120.9(5) . . ?
O1 C3 C2 121.5(5) . . ?
C4 C3 C2 117.5(4) . . ?
C5 C4 C3 122.4(5) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 O3 127.4(4) . . ?
C4 C5 C6 122.7(4) . . ?
O3 C5 C6 109.9(4) . . ?
O4 C6 C1 111.9(4) . . ?
O4 C6 C5 110.3(3) . . ?
C1 C6 C5 111.7(3) . . ?
O4 C6 C7 104.4(3) . . ?
C1 C6 C7 111.3(3) . . ?
C5 C6 C7 106.9(3) . . ?
C8 C7 C10 113.5(4) . . ?
C8 C7 C6 112.3(4) . . ?
C10 C7 C6 110.9(3) . . ?
C8 C7 H7 106.5 . . ?
C10 C7 H7 106.5 . . ?
C6 C7 H7 106.5 . . ?
C9 C8 C7 173.5(5) . . ?
C8 C9 H9 180.0 . . ?
C15 C10 C11 117.9(4) . . ?
C15 C10 C7 119.1(4) . . ?
C11 C10 C7 123.0(4) . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 Br1 118.8(4) . . ?
C12 C13 Br1 119.7(4) . . ?
C13 C14 C15 119.0(5) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C10 C15 C14 121.3(4) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C16 O2 C1 C2 -0.6(7) . . . . ?
C16 O2 C1 C6 179.8(4) . . . . ?
O2 C1 C2 C3 177.1(4) . . . . ?
C6 C1 C2 C3 -3.4(7) . . . . ?
C1 C2 C3 O1 -179.7(5) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
O1 C3 C4 C5 -179.3(5) . . . . ?
C2 C3 C4 C5 2.6(7) . . . . ?
C3 C4 C5 O3 -179.7(5) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C17 O3 C5 C4 -2.3(8) . . . . ?
C17 O3 C5 C6 176.9(4) . . . . ?
C18 O4 C6 C1 -65.4(5) . . . . ?
C18 O4 C6 C5 59.7(5) . . . . ?
C18 O4 C6 C7 174.2(4) . . . . ?
C2 C1 C6 O4 130.8(4) . . . . ?
O2 C1 C6 O4 -49.6(5) . . . . ?
C2 C1 C6 C5 6.5(6) . . . . ?
O2 C1 C6 C5 -173.9(4) . . . . ?
C2 C1 C6 C7 -112.9(5) . . . . ?
O2 C1 C6 C7 66.7(4) . . . . ?
C4 C5 C6 O4 -130.5(5) . . . . ?
O3 C5 C6 O4 50.2(5) . . . . ?
C4 C5 C6 C1 -5.4(6) . . . . ?
O3 C5 C6 C1 175.4(4) . . . . ?
C4 C5 C6 C7 116.6(5) . . . . ?
O3 C5 C6 C7 -62.6(4) . . . . ?
O4 C6 C7 C8 48.9(4) . . . . ?
C1 C6 C7 C8 -71.9(5) . . . . ?
C5 C6 C7 C8 165.8(4) . . . . ?
O4 C6 C7 C10 177.2(3) . . . . ?
C1 C6 C7 C10 56.3(5) . . . . ?
C5 C6 C7 C10 -66.0(4) . . . . ?
C8 C7 C10 C15 -141.0(4) . . . . ?
C6 C7 C10 C15 91.4(5) . . . . ?
C8 C7 C10 C11 41.5(6) . . . . ?
C6 C7 C10 C11 -86.1(5) . . . . ?
C15 C10 C11 C12 -2.2(7) . . . . ?
C7 C10 C11 C12 175.3(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 C14 1.9(7) . . . . ?
C11 C12 C13 Br1 -176.1(3) . . . . ?
C12 C13 C14 C15 -1.7(8) . . . . ?
Br1 C13 C14 C15 176.3(4) . . . . ?
C11 C10 C15 C14 2.4(7) . . . . ?
C7 C10 C15 C14 -175.2(4) . . . . ?
C13 C14 C15 C10 -0.5(7) . . . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



_chemical_compound_source        3,4,5-trimethoxyphenol
