# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
4-methoxy-2-(1-(naphthalen-2-ylsulfonyl)ethyl)phenol
_chemical_name_common            ?
_chemical_melting_point          'not determined'
_chemical_formula_moiety         'C19 H17 O4 S'
_chemical_formula_sum            'C19 H18 O4 S'
_chemical_compound_source        'Schomaker Lab No. SCS2037'
_exptl_crystal_recrystallization_method 'NMR sample was cooled to 7 °C slowly'
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_chemical_formula_weight         342.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ad

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

_cell_length_a                   5.50660(10)
_cell_length_b                   14.1867(2)
_cell_length_c                   20.9510(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1636.70(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      4.2204
_cell_measurement_theta_max      72.2300
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3123
_exptl_absorpt_correction_T_max  0.8156
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60° ω and 0.6° φ scans'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25180
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.76
_diffrn_reflns_theta_max         72.26
_reflns_number_total             3198
_reflns_number_gt                3155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 Ver. 2013.2-0 (Bruker-AXS, 2013)'
_computing_cell_refinement       'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997-2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997-2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997-2013)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997-2013)'

_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)+(0.0504P)²+0.3524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(14)
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H20 H 1.043(4) 0.4104(15) 0.7261(9) 0.017(5) Uiso 1 1 d . . .
C2 C 0.4283(3) 0.30349(11) 0.60498(7) 0.0159(3) Uani 1 1 d . . .
C3 C 0.4794(3) 0.39577(10) 0.62337(7) 0.0167(3) Uani 1 1 d . . .
H3 H 0.3848 0.4454 0.6084 0.020 Uiso 1 1 calc R . .
C4 C 0.6733(3) 0.41306(10) 0.66437(7) 0.0175(3) Uani 1 1 d . . .
H4 H 0.7073 0.4746 0.6768 0.021 Uiso 1 1 calc R . .
C5 C 0.8168(3) 0.33980(10) 0.68699(7) 0.0145(3) Uani 1 1 d . . .
C6 C 0.7643(3) 0.24702(9) 0.66912(6) 0.0136(3) Uani 1 1 d . . .
C7 C 0.5694(3) 0.23038(10) 0.62818(7) 0.0146(3) Uani 1 1 d . . .
H7 H 0.5335 0.1688 0.6162 0.018 Uiso 1 1 calc R . .
C9 C 0.9702(3) 0.08650(11) 0.64936(7) 0.0193(3) Uani 1 1 d . . .
H9C H 1.0630 0.0388 0.6709 0.029 Uiso 1 1 calc R . .
H9A H 1.0630 0.1113 0.6144 0.029 Uiso 1 1 calc R . .
H9B H 0.8223 0.0595 0.6335 0.029 Uiso 1 1 calc R . .
C8 C 0.9100(3) 0.16623(10) 0.69625(7) 0.0136(3) Uani 1 1 d . . .
H8 H 1.0626 0.1914 0.7132 0.016 Uiso 1 1 calc R . .
C10 C 0.7036(3) 0.20939(10) 0.81699(7) 0.0143(3) Uani 1 1 d . . .
C11 C 0.5054(3) 0.27212(11) 0.80957(7) 0.0169(3) Uani 1 1 d . . .
H11 H 0.3929 0.2633 0.7770 0.020 Uiso 1 1 calc R . .
C12 C 0.4828(3) 0.34569(11) 0.85113(7) 0.0190(3) Uani 1 1 d . . .
H12 H 0.3543 0.3876 0.8463 0.023 Uiso 1 1 calc R . .
C13 C 0.6512(3) 0.35952(10) 0.90152(7) 0.0173(3) Uani 1 1 d . . .
C14 C 0.8497(3) 0.29587(10) 0.90811(7) 0.0159(3) Uani 1 1 d . . .
C15 C 0.8724(3) 0.22024(10) 0.86439(7) 0.0154(3) Uani 1 1 d . . .
H15 H 1.0012 0.1782 0.8679 0.018 Uiso 1 1 calc R . .
C16 C 0.6280(3) 0.43444(11) 0.94590(8) 0.0221(3) Uani 1 1 d . . .
H16 H 0.4988 0.4763 0.9423 0.026 Uiso 1 1 calc R . .
C17 C 0.7943(3) 0.44576(12) 0.99411(8) 0.0243(4) Uani 1 1 d . . .
H17 H 0.7770 0.4952 1.0229 0.029 Uiso 1 1 calc R . .
C18 C 0.9918(3) 0.38265(13) 1.00025(8) 0.0242(3) Uani 1 1 d . . .
H18 H 1.1039 0.3910 1.0330 0.029 Uiso 1 1 calc R . .
C19 C 1.0190(3) 0.30954(11) 0.95846(7) 0.0200(3) Uani 1 1 d . . .
H19 H 1.1492 0.2684 0.9630 0.024 Uiso 1 1 calc R . .
C1 C 0.1058(3) 0.35177(12) 0.53651(8) 0.0229(3) Uani 1 1 d . . .
H1A H -0.0193 0.3254 0.5101 0.034 Uiso 1 1 calc R . .
H1C H 0.2121 0.3898 0.5109 0.034 Uiso 1 1 calc R . .
H1B H 0.0335 0.3901 0.5691 0.034 Uiso 1 1 calc R . .
O1 O 0.2409(2) 0.27775(7) 0.56529(5) 0.0207(2) Uani 1 1 d . . .
O2 O 1.0082(2) 0.35461(8) 0.72770(5) 0.0188(2) Uani 1 1 d . . .
O3 O 0.5010(2) 0.08851(7) 0.73913(5) 0.0197(2) Uani 1 1 d . . .
O4 O 0.8886(2) 0.04468(7) 0.79199(5) 0.0200(2) Uani 1 1 d . . .
S1 S 0.73836(6) 0.11599(2) 0.761745(16) 0.01400(10) 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
C2 O1 1.3745(19) . ?
C2 C7 1.384(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.392(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9300 . ?
C5 O2 1.3719(18) . ?
C5 C6 1.399(2) . ?
C6 C7 1.394(2) . ?
C6 C8 1.5102(19) . ?
C7 H7 0.9300 . ?
C9 C8 1.5345(19) . ?
C9 H9C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C8 S1 1.8123(15) . ?
C8 H8 0.9800 . ?
C10 C15 1.369(2) . ?
C10 C11 1.417(2) . ?
C10 S1 1.7699(15) . ?
C11 C12 1.365(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.419(2) . ?
C12 H12 0.9300 . ?
C13 C16 1.418(2) . ?
C13 C14 1.425(2) . ?
C14 C15 1.416(2) . ?
C14 C19 1.421(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C1 O1 1.4211(19) . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
O2 H20 0.82(2) . ?
O3 S1 1.4439(11) . ?
O4 S1 1.4525(11) . ?

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 C2 C7 115.78(13) . . ?
O1 C2 C3 124.64(14) . . ?
C7 C2 C3 119.57(14) . . ?
C4 C3 C2 119.40(14) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.00(14) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O2 C5 C4 122.31(13) . . ?
O2 C5 C6 117.99(13) . . ?
C4 C5 C6 119.69(14) . . ?
C7 C6 C5 118.89(13) . . ?
C7 C6 C8 120.81(13) . . ?
C5 C6 C8 120.24(13) . . ?
C2 C7 C6 121.43(13) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C8 C9 115.67(12) . . ?
C6 C8 S1 107.83(10) . . ?
C9 C8 S1 107.91(10) . . ?
C6 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
S1 C8 H8 108.4 . . ?
C15 C10 C11 122.14(14) . . ?
C15 C10 S1 119.02(11) . . ?
C11 C10 S1 118.81(11) . . ?
C12 C11 C10 118.74(14) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.37(14) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C16 C13 C12 122.18(15) . . ?
C16 C13 C14 118.74(14) . . ?
C12 C13 C14 119.08(14) . . ?
C15 C14 C19 121.73(14) . . ?
C15 C14 C13 119.02(14) . . ?
C19 C14 C13 119.25(14) . . ?
C10 C15 C14 119.64(13) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C13 120.66(15) . . ?
C17 C16 H16 119.7 . . ?
C13 C16 H16 119.7 . . ?
C16 C17 C18 120.39(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.43(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.53(15) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C2 O1 C1 116.96(12) . . ?
C5 O2 H20 107.7(14) . . ?
O3 S1 O4 118.08(7) . . ?
O3 S1 C10 108.60(7) . . ?
O4 S1 C10 107.32(7) . . ?
O3 S1 C8 109.26(7) . . ?
O4 S1 C8 107.89(7) . . ?
C10 S1 C8 104.90(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 C2 C3 C4 179.42(13) . . . . ?
C7 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 O2 -179.63(13) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
O2 C5 C6 C7 179.50(13) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
O2 C5 C6 C8 2.2(2) . . . . ?
C4 C5 C6 C8 -176.58(13) . . . . ?
O1 C2 C7 C6 -179.70(13) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C8 C6 C7 C2 177.39(13) . . . . ?
C7 C6 C8 C9 42.10(19) . . . . ?
C5 C6 C8 C9 -140.67(14) . . . . ?
C7 C6 C8 S1 -78.77(15) . . . . ?
C5 C6 C8 S1 98.46(14) . . . . ?
C15 C10 C11 C12 0.0(2) . . . . ?
S1 C10 C11 C12 -178.16(12) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C16 -178.74(15) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C16 C13 C14 C15 179.26(14) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C16 C13 C14 C19 -0.4(2) . . . . ?
C12 C13 C14 C19 179.93(14) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
S1 C10 C15 C14 178.65(11) . . . . ?
C19 C14 C15 C10 179.39(14) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C12 C13 C16 C17 180.00(15) . . . . ?
C14 C13 C16 C17 0.3(2) . . . . ?
C13 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 -179.50(15) . . . . ?
C13 C14 C19 C18 0.2(2) . . . . ?
C7 C2 O1 C1 -174.85(13) . . . . ?
C3 C2 O1 C1 6.3(2) . . . . ?
C15 C10 S1 O3 151.50(11) . . . . ?
C11 C10 S1 O3 -30.27(13) . . . . ?
C15 C10 S1 O4 22.81(14) . . . . ?
C11 C10 S1 O4 -158.96(11) . . . . ?
C15 C10 S1 C8 -91.77(12) . . . . ?
C11 C10 S1 C8 86.46(12) . . . . ?
C6 C8 S1 O3 56.14(11) . . . . ?
C9 C8 S1 O3 -69.47(12) . . . . ?
C6 C8 S1 O4 -174.31(9) . . . . ?
C9 C8 S1 O4 60.09(11) . . . . ?
C6 C8 S1 C10 -60.13(11) . . . . ?
C9 C8 S1 C10 174.27(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.001
_diffrn_reflns_theta_full        72.26
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 985120'
