# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_3phendiacid
_database_code_depnum_ccdc_archive 'CCDC 1040894'
_audit_update_record             
;
2014-12-23 deposited with the CCDC.
2015-12-15 downloaded from the CCDC.
;
_audit_creation_date             08-10-30
_audit_creation_method           CRYSTALS_ver_12.85

_oxford_structure_analysis_title 005mwj08
_chemical_name_systematic        
"2',5'-dihexyl-[1,1':4',1''-terphenyl]-4,4''-dicarboxylic acid "
_chemical_melting_point          'not measured'

_cell_length_a                   14.1458(4)
_cell_length_b                   7.2193(2)
_cell_length_c                   17.4712(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5591(13)
_cell_angle_gamma                90
_cell_volume                     1764.34(8)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1 '
_symmetry_space_group_name_Hall  '-P 2yab '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C34 H44 O5 S1 
# Dc =      1.06 Fooo =    692.00 Mu =      1.26 M =    282.39
# Found Formula = C36 H50 O6 S2 
# Dc =      1.21 FOOO =    692.00 Mu =      1.93 M =    321.46

_chemical_formula_sum            'C36 H50 O6 S2'
_chemical_formula_moiety         'C32 H38 O4, 2(C2 H6 O S)'
_chemical_compound_source        .
_chemical_formula_weight         642.92


_cell_measurement_reflns_used    4163
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.26

_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.193

# Sheldrick geometric approximatio 0.96 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            7666
_reflns_number_total             4019
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections with Friedels Law is 4019 
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 4049 


_diffrn_reflns_theta_min         5.166
_diffrn_reflns_theta_max         27.490
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        25.565
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.62
_oxford_diffrn_Wilson_scale      2.69

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.49


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0443
_refine_ls_wR_factor_ref         0.1099
_refine_ls_goodness_of_fit_ref   1.0027
_refine_ls_shift/su_max          0.000217


# The values computed from all data 
_oxford_reflns_number_all        4019
_refine_ls_R_factor_all          0.0746
_refine_ls_wR_factor_all         0.1267

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2872
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_gt          0.1143

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.90P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
S1 S 0.15872(4) 0.54642(9) -0.01458(3) 0.0402 1.0000 Uani . . . . . . .
O2 O 0.07376(11) 0.5152(2) -0.07666(8) 0.0398 1.0000 Uani . . . . . . .
O3 O 0.36832(12) 0.5796(2) 0.11543(8) 0.0454 1.0000 Uani . . . . . . .
C4 C 0.40413(14) 0.6321(3) 0.17934(11) 0.0289 1.0000 Uani . . . . . . .
O5 O 0.42946(11) 0.8052(2) 0.19495(8) 0.0392 1.0000 Uani . . . . . . .
C6 C 0.42421(13) 0.5067(3) 0.24756(10) 0.0256 1.0000 Uani . . . . . . .
C7 C 0.41868(15) 0.3171(3) 0.23601(11) 0.0329 1.0000 Uani . . . . . . .
C8 C 0.43919(15) 0.1969(3) 0.29790(11) 0.0322 1.0000 Uani . . . . . . .
C9 C 0.46573(13) 0.2627(3) 0.37298(10) 0.0255 1.0000 Uani . . . . . . .
C10 C 0.48642(13) 0.1293(3) 0.43917(10) 0.0252 1.0000 Uani . . . . . . .
C11 C 0.40931(14) 0.0545(3) 0.47031(10) 0.0267 1.0000 Uani . . . . . . .
C12 C 0.42023(14) -0.0739(3) 0.53101(10) 0.0265 1.0000 Uani . . . . . . .
C13 C 0.33327(14) -0.1423(3) 0.56319(11) 0.0314 1.0000 Uani . . . . . . .
C14 C 0.31950(15) -0.0532(3) 0.64042(11) 0.0336 1.0000 Uani . . . . . . .
C15 C 0.30679(15) 0.1558(3) 0.63731(11) 0.0358 1.0000 Uani . . . . . . .
C16 C 0.31216(15) 0.2460(3) 0.71657(11) 0.0358 1.0000 Uani . . . . . . .
C17 C 0.29852(18) 0.4545(3) 0.71256(12) 0.0444 1.0000 Uani . . . . . . .
C18 C 0.3088(2) 0.5492(4) 0.79089(13) 0.0488 1.0000 Uani . . . . . . .
C19 C 0.47005(16) 0.4534(3) 0.38389(11) 0.0338 1.0000 Uani . . . . . . .
C20 C 0.45008(16) 0.5741(3) 0.32216(11) 0.0334 1.0000 Uani . . . . . . .
C21 C 0.1273(2) 0.7451(4) 0.03605(14) 0.0524 1.0000 Uani . . . . . . .
C22 C 0.15054(18) 0.3779(4) 0.05812(14) 0.0501 1.0000 Uani . . . . . . .
H71 H 0.4022 0.2690 0.1865 0.0396 1.0000 Uiso R . . . . . .
H81 H 0.4350 0.0673 0.2882 0.0404 1.0000 Uiso R . . . . . .
H111 H 0.3466 0.0944 0.4497 0.0318 1.0000 Uiso R . . . . . .
H132 H 0.3390 -0.2763 0.5703 0.0382 1.0000 Uiso R . . . . . .
H131 H 0.2764 -0.1170 0.5241 0.0370 1.0000 Uiso R . . . . . .
H141 H 0.3761 -0.0800 0.6775 0.0406 1.0000 Uiso R . . . . . .
H142 H 0.2639 -0.1082 0.6586 0.0413 1.0000 Uiso R . . . . . .
H152 H 0.3562 0.2104 0.6115 0.0432 1.0000 Uiso R . . . . . .
H151 H 0.2451 0.1805 0.6078 0.0422 1.0000 Uiso R . . . . . .
H162 H 0.3756 0.2225 0.7474 0.0428 1.0000 Uiso R . . . . . .
H161 H 0.2631 0.1912 0.7428 0.0439 1.0000 Uiso R . . . . . .
H171 H 0.3463 0.5049 0.6839 0.0538 1.0000 Uiso R . . . . . .
H172 H 0.2348 0.4799 0.6858 0.0540 1.0000 Uiso R . . . . . .
H182 H 0.3016 0.6821 0.7874 0.0739 1.0000 Uiso R . . . . . .
H181 H 0.3712 0.5202 0.8191 0.0737 1.0000 Uiso R . . . . . .
H183 H 0.2616 0.5005 0.8202 0.0736 1.0000 Uiso R . . . . . .
H191 H 0.4880 0.4998 0.4345 0.0408 1.0000 Uiso R . . . . . .
H201 H 0.4524 0.7033 0.3313 0.0408 1.0000 Uiso R . . . . . .
H223 H 0.0907 0.3896 0.0765 0.0738 1.0000 Uiso R . . . . . .
H213 H 0.0676 0.7215 0.0526 0.0778 1.0000 Uiso R . . . . . .
H222 H 0.2023 0.3982 0.0981 0.0746 1.0000 Uiso R . . . . . .
H221 H 0.1556 0.2549 0.0363 0.0747 1.0000 Uiso R . . . . . .
H212 H 0.1217 0.8444 0.0001 0.0787 1.0000 Uiso R . . . . . .
H211 H 0.1774 0.7695 0.0771 0.0790 1.0000 Uiso R . . . . . .
H51 H 0.4220 0.8683 0.1540 0.0589 1.0000 Uiso R . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4594(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O2 . 1.5112(15) yes
S1 . C21 . 1.776(2) yes
S1 . C22 . 1.775(2) yes
O3 . C4 . 1.216(2) yes
C4 . O5 . 1.317(2) yes
C4 . C6 . 1.490(3) yes
O5 . H51 . 0.841 no
C6 . C7 . 1.384(3) yes
C6 . C20 . 1.388(3) yes
C7 . C8 . 1.383(3) yes
C7 . H71 . 0.929 no
C8 . C9 . 1.393(3) yes
C8 . H81 . 0.951 no
C9 . C10 . 1.500(3) yes
C9 . C19 . 1.390(3) yes
C10 . C12 2_656 1.404(3) yes
C10 . C11 . 1.398(3) yes
C11 . C12 . 1.400(3) yes
C11 . H111 . 0.952 no
C12 . C13 . 1.510(3) yes
C13 . C14 . 1.533(3) yes
C13 . H132 . 0.977 no
C13 . H131 . 0.991 no
C14 . C15 . 1.520(3) yes
C14 . H141 . 0.972 no
C14 . H142 . 0.976 no
C15 . C16 . 1.522(3) yes
C15 . H152 . 0.971 no
C15 . H151 . 0.962 no
C16 . C17 . 1.518(3) yes
C16 . H162 . 0.989 no
C16 . H161 . 0.971 no
C17 . C18 . 1.517(3) yes
C17 . H171 . 0.970 no
C17 . H172 . 0.970 no
C18 . H182 . 0.966 no
C18 . H181 . 0.968 no
C18 . H183 . 0.966 no
C19 . C20 . 1.383(3) yes
C19 . H191 . 0.944 no
C20 . H201 . 0.946 no
C21 . H213 . 0.949 no
C21 . H212 . 0.949 no
C21 . H211 . 0.947 no
C22 . H223 . 0.952 no
C22 . H222 . 0.945 no
C22 . H221 . 0.973 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . S1 . C21 . 104.30(11) yes
O2 . S1 . C22 . 106.36(11) yes
C21 . S1 . C22 . 98.60(13) yes
O3 . C4 . O5 . 123.30(18) yes
O3 . C4 . C6 . 123.28(19) yes
O5 . C4 . C6 . 113.41(16) yes
C4 . O5 . H51 . 110.0 no
C4 . C6 . C7 . 118.97(17) yes
C4 . C6 . C20 . 122.03(18) yes
C7 . C6 . C20 . 118.99(18) yes
C6 . C7 . C8 . 120.38(18) yes
C6 . C7 . H71 . 120.4 no
C8 . C7 . H71 . 119.2 no
C7 . C8 . C9 . 121.18(19) yes
C7 . C8 . H81 . 118.5 no
C9 . C8 . H81 . 120.3 no
C8 . C9 . C10 . 120.06(17) yes
C8 . C9 . C19 . 117.87(17) yes
C10 . C9 . C19 . 122.06(17) yes
C9 . C10 . C12 2_656 122.27(17) yes
C9 . C10 . C11 . 118.29(17) yes
C12 2_656 C10 . C11 . 119.41(17) yes
C10 . C11 . C12 . 123.10(18) yes
C10 . C11 . H111 . 118.3 no
C12 . C11 . H111 . 118.6 no
C10 2_656 C12 . C11 . 117.48(17) yes
C10 2_656 C12 . C13 . 122.82(17) yes
C11 . C12 . C13 . 119.67(17) yes
C12 . C13 . C14 . 114.05(17) yes
C12 . C13 . H132 . 108.3 no
C14 . C13 . H132 . 108.8 no
C12 . C13 . H131 . 107.8 no
C14 . C13 . H131 . 109.4 no
H132 . C13 . H131 . 108.3 no
C13 . C14 . C15 . 114.52(17) yes
C13 . C14 . H141 . 107.7 no
C15 . C14 . H141 . 107.6 no
C13 . C14 . H142 . 109.3 no
C15 . C14 . H142 . 108.6 no
H141 . C14 . H142 . 109.0 no
C14 . C15 . C16 . 113.75(17) yes
C14 . C15 . H152 . 109.3 no
C16 . C15 . H152 . 107.9 no
C14 . C15 . H151 . 107.2 no
C16 . C15 . H151 . 109.0 no
H152 . C15 . H151 . 109.6 no
C15 . C16 . C17 . 113.18(17) yes
C15 . C16 . H162 . 109.9 no
C17 . C16 . H162 . 107.1 no
C15 . C16 . H161 . 108.2 no
C17 . C16 . H161 . 109.3 no
H162 . C16 . H161 . 109.0 no
C16 . C17 . C18 . 114.26(19) yes
C16 . C17 . H171 . 107.6 no
C18 . C17 . H171 . 108.5 no
C16 . C17 . H172 . 108.2 no
C18 . C17 . H172 . 107.9 no
H171 . C17 . H172 . 110.4 no
C17 . C18 . H182 . 113.3 no
C17 . C18 . H181 . 108.6 no
H182 . C18 . H181 . 109.1 no
C17 . C18 . H183 . 109.4 no
H182 . C18 . H183 . 108.7 no
H181 . C18 . H183 . 107.5 no
C9 . C19 . C20 . 121.16(18) yes
C9 . C19 . H191 . 118.7 no
C20 . C19 . H191 . 120.1 no
C6 . C20 . C19 . 120.42(19) yes
C6 . C20 . H201 . 120.1 no
C19 . C20 . H201 . 119.4 no
S1 . C21 . H213 . 107.9 no
S1 . C21 . H212 . 106.4 no
H213 . C21 . H212 . 110.3 no
S1 . C21 . H211 . 108.3 no
H213 . C21 . H211 . 113.6 no
H212 . C21 . H211 . 110.0 no
S1 . C22 . H223 . 109.7 no
S1 . C22 . H222 . 107.2 no
H223 . C22 . H222 . 111.5 no
S1 . C22 . H221 . 109.2 no
H223 . C22 . H221 . 109.5 no
H222 . C22 . H221 . 109.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H81 . O5 1_545 149 0.95 2.49 3.343(3) yes
C22 . H223 . O2 2_565 158 0.95 2.43 3.328(3) yes
O5 . H51 . O2 3_555 170 0.84 1.73 2.558(3) yes
_chemical_name_common            '3phenyl diacid'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
_exptl_crystal_preparation       'NMR, mass spectrometry'
