# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_SM6f-285
_database_code_depnum_ccdc_archive 'CCDC 1526470'
_audit_update_record             
;
2017-01-10 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"2-Methoxy-4'-phenyl-[1,1':2',1''-terphenyl]-3'-ol (9d)"
_chemical_name_common            ?
_chemical_melting_point          434
_chemical_formula_moiety         'C25 H20 O2'
_chemical_formula_sum            'C25 H20 O2'
_chemical_formula_weight         352.41

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.5607(9)
_cell_length_b                   10.2840(10)
_cell_length_c                   10.9413(10)
_cell_angle_alpha                100.114(4)
_cell_angle_beta                 114.210(4)
_cell_angle_gamma                102.160(4)
_cell_volume                     916.80(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.95

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6991
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54615
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.119
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4586
_reflns_number_gt                3445
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0628P)²+0.1679P] 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         4586
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.71877(14) 0.28456(12) 0.04378(12) 0.0293(3) Uani 1 1 d . . . . .
C2 C 0.75282(14) 0.18634(12) 0.11650(12) 0.0280(2) Uani 1 1 d . . . . .
C3 C 0.80949(14) 0.08423(12) 0.06771(12) 0.0294(3) Uani 1 1 d . . . . .
C4 C 0.83440(15) 0.08457(14) -0.04914(14) 0.0351(3) Uani 1 1 d . . . . .
H4 H 0.8719 0.0159 -0.0824 0.042 Uiso 1 1 calc R U . . .
C5 C 0.80448(15) 0.18474(14) -0.11638(14) 0.0346(3) Uani 1 1 d . . . . .
H5 H 0.8256 0.1849 -0.1930 0.041 Uiso 1 1 calc R U . . .
C6 C 0.74397(14) 0.28522(12) -0.07365(13) 0.0301(3) Uani 1 1 d . . . . .
O1 O 0.65918(13) 0.38471(9) 0.08450(10) 0.0401(2) Uani 1 1 d . . . . .
H1 H 0.6362 0.3689 0.1470 0.060 Uiso 1 1 calc R U . . .
C7 C 0.72324(14) 0.19287(12) 0.24115(12) 0.0298(3) Uani 1 1 d . . . . .
C8 C 0.80740(17) 0.30989(14) 0.35797(14) 0.0391(3) Uani 1 1 d . . . . .
H8 H 0.8875 0.3826 0.3602 0.047 Uiso 1 1 calc R U . . .
C9 C 0.77499(19) 0.32078(16) 0.47086(15) 0.0460(4) Uani 1 1 d . . . . .
H9 H 0.8324 0.4009 0.5486 0.055 Uiso 1 1 calc R U . . .
C10 C 0.65934(19) 0.21507(19) 0.46985(15) 0.0494(4) Uani 1 1 d . . . . .
H10 H 0.6367 0.2230 0.5462 0.059 Uiso 1 1 calc R U . . .
C11 C 0.57645(18) 0.09709(18) 0.35611(16) 0.0481(4) Uani 1 1 d . . . . .
H11 H 0.4987 0.0238 0.3560 0.058 Uiso 1 1 calc R U . . .
C12 C 0.60720(16) 0.08582(15) 0.24163(14) 0.0378(3) Uani 1 1 d . . . . .
H12 H 0.5493 0.0055 0.1642 0.045 Uiso 1 1 calc R U . . .
C13 C 0.83984(15) -0.02867(12) 0.13441(13) 0.0305(3) Uani 1 1 d . . . . .
C14 C 0.96575(15) -0.00204(13) 0.26908(13) 0.0332(3) Uani 1 1 d . . . . .
C15 C 0.99164(17) -0.11058(15) 0.32602(16) 0.0414(3) Uani 1 1 d . . . . .
H15 H 1.0747 -0.0923 0.4172 0.050 Uiso 1 1 calc R U . . .
C16 C 0.89410(19) -0.24604(15) 0.24747(17) 0.0453(4) Uani 1 1 d . . . . .
H16 H 0.9115 -0.3193 0.2863 0.054 Uiso 1 1 calc R U . . .
C17 C 0.77270(19) -0.27471(14) 0.11409(17) 0.0449(3) Uani 1 1 d . . . . .
H17 H 0.7083 -0.3670 0.0610 0.054 Uiso 1 1 calc R U . . .
C18 C 0.74619(17) -0.16570(14) 0.05857(15) 0.0388(3) Uani 1 1 d . . . . .
H18 H 0.6627 -0.1851 -0.0327 0.047 Uiso 1 1 calc R U . . .
O2 O 1.05942(12) 0.13430(10) 0.33592(10) 0.0466(3) Uani 1 1 d . . . . .
C19 C 1.20806(19) 0.16216(19) 0.45682(16) 0.0551(4) Uani 1 1 d . . . . .
H19A H 1.1875 0.1319 0.5287 0.083 Uiso 1 1 calc R U . . .
H19B H 1.2651 0.2613 0.4915 0.083 Uiso 1 1 calc R U . . .
H19C H 1.2734 0.1124 0.4331 0.083 Uiso 1 1 calc R U . . .
C20 C 0.70713(15) 0.38991(13) -0.15022(12) 0.0308(3) Uani 1 1 d . . . . .
C21 C 0.82694(17) 0.47907(14) -0.16503(13) 0.0374(3) Uani 1 1 d . . . . .
H21 H 0.9316 0.4714 -0.1286 0.045 Uiso 1 1 calc R U . . .
C22 C 0.7935(2) 0.57891(15) -0.23280(15) 0.0461(4) Uani 1 1 d . . . . .
H22 H 0.8762 0.6405 -0.2394 0.055 Uiso 1 1 calc R U . . .
C23 C 0.6391(2) 0.58803(16) -0.29059(16) 0.0504(4) Uani 1 1 d . . . . .
H23 H 0.6163 0.6555 -0.3371 0.060 Uiso 1 1 calc R U . . .
C24 C 0.51849(19) 0.49812(17) -0.28006(15) 0.0468(4) Uani 1 1 d . . . . .
H24 H 0.4128 0.5031 -0.3212 0.056 Uiso 1 1 calc R U . . .
C25 C 0.55197(17) 0.40061(15) -0.20934(14) 0.0387(3) Uani 1 1 d . . . . .
H25 H 0.4692 0.3410 -0.2011 0.046 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
C1 O1 1.3705(14) . ?
C1 C6 1.4019(16) . ?
C1 C2 1.4027(16) . ?
C2 C3 1.4005(16) . ?
C2 C7 1.4955(16) . ?
C3 C4 1.3936(17) . ?
C3 C13 1.4935(16) . ?
C4 C5 1.3790(18) . ?
C4 H4 0.9400 . ?
C5 C6 1.3875(17) . ?
C5 H5 0.9400 . ?
C6 C20 1.4898(16) . ?
O1 H1 0.8300 . ?
C7 C12 1.3911(18) . ?
C7 C8 1.3921(18) . ?
C8 C9 1.3835(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.373(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.3907(19) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.3873(18) . ?
C13 C14 1.4000(18) . ?
C14 O2 1.3699(16) . ?
C14 C15 1.3891(18) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.371(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.3866(19) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
O2 C19 1.4161(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 C25 1.3921(18) . ?
C20 C21 1.3932(17) . ?
C21 C22 1.3847(19) . ?
C21 H21 0.9400 . ?
C22 C23 1.379(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.377(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.3825(19) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?

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 C6 116.81(10) . . ?
O1 C1 C2 121.40(10) . . ?
C6 C1 C2 121.79(11) . . ?
C3 C2 C1 118.79(10) . . ?
C3 C2 C7 122.62(10) . . ?
C1 C2 C7 118.57(10) . . ?
C4 C3 C2 119.49(11) . . ?
C4 C3 C13 118.41(11) . . ?
C2 C3 C13 122.07(10) . . ?
C5 C4 C3 120.60(11) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.62(11) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.66(11) . . ?
C5 C6 C20 121.01(11) . . ?
C1 C6 C20 121.32(11) . . ?
C1 O1 H1 109.5 . . ?
C12 C7 C8 118.27(12) . . ?
C12 C7 C2 121.33(11) . . ?
C8 C7 C2 120.34(11) . . ?
C9 C8 C7 121.02(13) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 120.26(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.65(13) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.46(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.32(13) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C18 C13 C14 118.35(11) . . ?
C18 C13 C3 119.36(12) . . ?
C14 C13 C3 122.20(11) . . ?
O2 C14 C15 123.98(12) . . ?
O2 C14 C13 115.72(11) . . ?
C15 C14 C13 120.29(12) . . ?
C16 C15 C14 119.59(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 121.03(13) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.07(13) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 121.63(13) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C14 O2 C19 117.43(12) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.35(12) . . ?
C25 C20 C6 120.83(11) . . ?
C21 C20 C6 120.81(11) . . ?
C22 C21 C20 120.72(13) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.06(13) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 119.83(13) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 120.38(14) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.60(13) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?

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 178.34(11) . . . . ?
C6 C1 C2 C3 -1.70(17) . . . . ?
O1 C1 C2 C7 -0.20(17) . . . . ?
C6 C1 C2 C7 179.77(11) . . . . ?
C1 C2 C3 C4 1.57(17) . . . . ?
C7 C2 C3 C4 -179.97(11) . . . . ?
C1 C2 C3 C13 -176.56(11) . . . . ?
C7 C2 C3 C13 1.91(18) . . . . ?
C2 C3 C4 C5 0.31(18) . . . . ?
C13 C3 C4 C5 178.50(12) . . . . ?
C3 C4 C5 C6 -2.2(2) . . . . ?
C4 C5 C6 C1 2.00(19) . . . . ?
C4 C5 C6 C20 -177.96(12) . . . . ?
O1 C1 C6 C5 179.91(11) . . . . ?
C2 C1 C6 C5 -0.06(17) . . . . ?
O1 C1 C6 C20 -0.13(17) . . . . ?
C2 C1 C6 C20 179.90(11) . . . . ?
C3 C2 C7 C12 -63.18(16) . . . . ?
C1 C2 C7 C12 115.29(13) . . . . ?
C3 C2 C7 C8 119.50(13) . . . . ?
C1 C2 C7 C8 -62.03(16) . . . . ?
C12 C7 C8 C9 -1.02(19) . . . . ?
C2 C7 C8 C9 176.37(12) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -1.2(2) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C8 C7 C12 C11 0.42(19) . . . . ?
C2 C7 C12 C11 -176.95(12) . . . . ?
C4 C3 C13 C18 -63.52(16) . . . . ?
C2 C3 C13 C18 114.62(14) . . . . ?
C4 C3 C13 C14 113.04(13) . . . . ?
C2 C3 C13 C14 -68.81(16) . . . . ?
C18 C13 C14 O2 176.63(11) . . . . ?
C3 C13 C14 O2 0.03(17) . . . . ?
C18 C13 C14 C15 -2.12(18) . . . . ?
C3 C13 C14 C15 -178.72(11) . . . . ?
O2 C14 C15 C16 -177.26(12) . . . . ?
C13 C14 C15 C16 1.38(19) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C17 C18 C13 0.3(2) . . . . ?
C14 C13 C18 C17 1.30(19) . . . . ?
C3 C13 C18 C17 178.00(12) . . . . ?
C15 C14 O2 C19 12.71(19) . . . . ?
C13 C14 O2 C19 -165.98(12) . . . . ?
C5 C6 C20 C25 121.14(14) . . . . ?
C1 C6 C20 C25 -58.82(16) . . . . ?
C5 C6 C20 C21 -58.53(17) . . . . ?
C1 C6 C20 C21 121.51(13) . . . . ?
C25 C20 C21 C22 2.15(19) . . . . ?
C6 C20 C21 C22 -178.17(12) . . . . ?
C20 C21 C22 C23 -2.1(2) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C23 C24 C25 C20 -1.3(2) . . . . ?
C21 C20 C25 C24 -0.44(19) . . . . ?
C6 C20 C25 C24 179.88(12) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/ethyl acetate'
