# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Jerry L. Atwood'
_publ_contact_author_address     
;
Chemistry
University of Missouri - Columbia
125 Chemistry
Columbia
MO
UNITED STATES OF AMERICA
;

_publ_contact_author_email       ATWOODJ@MISSOURI.EDU

_publ_section_title              
;
Crystal engineering of nonporous organic solids for
methane sorption
;
loop_
_publ_author_name
'J. L. Atwood'
'Leonard J. Barbour'
'Praveen Kumar Thallapally'
'Trevor B. Wirsig'

data_D:\X-Ray\_Praveen\Pentyl\pentyl.CIF
_database_code_depnum_ccdc_archive 'CCDC 273602'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Pentyl
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H64 O4'
_chemical_formula_weight         704.99

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P4/n

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

_cell_length_a                   12.717(3)
_cell_length_b                   12.717(3)
_cell_length_c                   13.457(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2176.2(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14207
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.13
_reflns_number_total             2398
_reflns_number_gt                1488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  SHELX-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1037P)^2^+1.6329P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2398
_refine_ls_number_parameters     150
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0823
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.2016
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.006
_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
O1 O 0.18459(15) 0.11542(16) 0.55149(15) 0.0282(5) Uani 1 1 d . . .
C6 C 0.0574(2) 0.0843(2) 0.4208(2) 0.0228(6) Uani 1 1 d . . .
C2 C 0.2274(2) -0.00475(19) 0.4213(2) 0.0216(6) Uani 1 1 d . . .
C7 C -0.0204(2) 0.1631(2) 0.4637(2) 0.0250(6) Uani 1 1 d . . .
H7A H -0.0929 0.1393 0.4492 0.030 Uiso 1 1 calc R . .
H7B H -0.0119 0.1657 0.5368 0.030 Uiso 1 1 calc R . .
C1 C 0.1557(2) 0.06601(19) 0.4638(2) 0.0223(6) Uani 1 1 d . . .
C3 C 0.1976(2) -0.0572(2) 0.3364(2) 0.0249(7) Uani 1 1 d . . .
H3 H 0.2457 -0.1058 0.3079 0.030 Uiso 1 1 calc R . .
C5 C 0.0323(2) 0.0298(2) 0.3346(2) 0.0246(7) Uani 1 1 d . . .
H5 H -0.0341 0.0423 0.3044 0.030 Uiso 1 1 calc R . .
C4 C 0.1004(2) -0.0430(2) 0.2899(2) 0.0267(7) Uani 1 1 d . A .
C8 C 0.0721(2) -0.1028(3) 0.1955(3) 0.0374(8) Uani 1 1 d . . .
C9 C 0.0748(5) -0.2220(4) 0.2203(5) 0.0460(16) Uani 0.687(8) 1 d P A 1
H9A H 0.1446 -0.2408 0.2456 0.069 Uiso 0.687(8) 1 calc PR A 1
H9B H 0.0599 -0.2627 0.1601 0.069 Uiso 0.687(8) 1 calc PR A 1
H9C H 0.0216 -0.2377 0.2709 0.069 Uiso 0.687(8) 1 calc PR A 1
C12 C 0.1778(4) 0.0334(4) 0.0929(3) 0.0783(16) Uani 0.687(8) 1 d PD A 1
H12A H 0.2327 0.0388 0.0420 0.117 Uiso 0.687(8) 1 calc PR A 1
H12B H 0.2010 0.0693 0.1535 0.117 Uiso 0.687(8) 1 calc PR A 1
H12C H 0.1130 0.0662 0.0684 0.117 Uiso 0.687(8) 1 calc PR A 1
C11 C 0.1571(4) -0.0817(4) 0.1158(4) 0.0450(16) Uani 0.687(8) 1 d PD A 1
H11A H 0.2238 -0.1142 0.1380 0.054 Uiso 0.687(8) 1 calc PR A 1
H11B H 0.1357 -0.1172 0.0535 0.054 Uiso 0.687(8) 1 calc PR A 1
C10 C -0.0363(5) -0.0746(6) 0.1557(5) 0.0521(18) Uani 0.687(8) 1 d P A 1
H10A H -0.0503 -0.1152 0.0953 0.078 Uiso 0.687(8) 1 calc PR A 1
H10B H -0.0387 0.0007 0.1403 0.078 Uiso 0.687(8) 1 calc PR A 1
H10C H -0.0896 -0.0910 0.2060 0.078 Uiso 0.687(8) 1 calc PR A 1
C11' C 0.0737(10) -0.0255(12) 0.1062(10) 0.067(5) Uani 0.313(8) 1 d PD A 2
H11C H 0.0586 -0.0654 0.0447 0.080 Uiso 0.313(8) 1 calc PR A 2
H11D H 0.0167 0.0266 0.1151 0.080 Uiso 0.313(8) 1 calc PR A 2
C10' C -0.0454(11) -0.1397(15) 0.1965(14) 0.071(5) Uani 0.313(8) 1 d P A 2
H10D H -0.0910 -0.0799 0.2123 0.106 Uiso 0.313(8) 1 calc PR A 2
H10E H -0.0546 -0.1947 0.2467 0.106 Uiso 0.313(8) 1 calc PR A 2
H10F H -0.0642 -0.1676 0.1309 0.106 Uiso 0.313(8) 1 calc PR A 2
C9' C 0.1323(18) -0.2008(14) 0.1718(14) 0.089(7) Uani 0.313(8) 1 d P A 2
H9'1 H 0.1059 -0.2309 0.1096 0.133 Uiso 0.313(8) 1 calc PR A 2
H9'2 H 0.1232 -0.2518 0.2257 0.133 Uiso 0.313(8) 1 calc PR A 2
H9'3 H 0.2070 -0.1838 0.1646 0.133 Uiso 0.313(8) 1 calc PR A 2
C12' C 0.1778(4) 0.0334(4) 0.0929(3) 0.0783(16) Uani 0.31 1 d PD A 2
H12D H 0.1755 0.0742 0.0312 0.117 Uiso 0.313(8) 1 calc PR A 2
H12E H 0.2357 -0.0173 0.0897 0.117 Uiso 0.313(8) 1 calc PR A 2
H12F H 0.1887 0.0809 0.1493 0.117 Uiso 0.313(8) 1 calc PR A 2
H1 H 0.156(4) 0.170(4) 0.565(4) 0.13(2) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0258(11) 0.0259(11) 0.0328(12) 0.0008(9) -0.0023(8) 0.0005(9)
C6 0.0188(13) 0.0157(13) 0.0340(16) 0.0076(11) 0.0077(11) 0.0012(10)
C2 0.0192(13) 0.0160(13) 0.0297(16) 0.0075(11) 0.0012(11) -0.0009(10)
C7 0.0157(13) 0.0210(13) 0.0382(17) 0.0036(12) 0.0047(12) 0.0010(10)
C1 0.0230(13) 0.0150(12) 0.0290(15) 0.0030(11) 0.0029(11) -0.0019(10)
C3 0.0184(13) 0.0186(13) 0.0377(18) 0.0011(12) 0.0030(12) 0.0014(10)
C5 0.0161(13) 0.0211(13) 0.0367(17) 0.0045(12) -0.0033(11) -0.0014(10)
C4 0.0219(14) 0.0215(14) 0.0367(17) 0.0004(12) 0.0007(12) -0.0007(11)
C8 0.0292(16) 0.0359(17) 0.047(2) -0.0087(15) -0.0060(14) 0.0031(14)
C9 0.048(3) 0.026(3) 0.064(4) -0.016(3) -0.010(3) -0.009(2)
C12 0.093(4) 0.085(4) 0.057(3) 0.015(3) 0.007(3) -0.025(3)
C11 0.043(3) 0.050(3) 0.042(3) -0.009(2) -0.001(2) 0.006(2)
C10 0.040(3) 0.057(4) 0.059(4) -0.026(3) -0.025(3) 0.017(3)
C11' 0.058(9) 0.091(11) 0.051(8) -0.018(7) -0.011(6) -0.001(8)
C10' 0.055(8) 0.062(10) 0.096(13) -0.039(9) -0.016(8) -0.004(8)
C9' 0.120(17) 0.070(12) 0.076(13) -0.037(10) -0.046(12) 0.032(11)
C12' 0.093(4) 0.085(4) 0.057(3) 0.015(3) 0.007(3) -0.025(3)

_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
O1 C1 1.386(3) . ?
C6 C5 1.390(4) . ?
C6 C1 1.397(4) . ?
C6 C7 1.521(4) . ?
C2 C3 1.377(4) . ?
C2 C1 1.403(4) . ?
C2 C7 1.517(4) 2 ?
C7 C2 1.517(4) 4 ?
C3 C4 1.397(4) . ?
C5 C4 1.402(4) . ?
C4 C8 1.523(4) . ?
C8 C9' 1.497(16) . ?
C8 C10 1.521(6) . ?
C8 C9 1.553(6) . ?
C8 C11 1.547(6) . ?
C8 C11' 1.553(15) . ?
C8 C10' 1.567(15) . ?
C12 C11 1.518(7) . ?

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
C5 C6 C1 117.9(2) . . ?
C5 C6 C7 119.8(2) . . ?
C1 C6 C7 122.3(3) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 C7 120.1(2) . 2 ?
C1 C2 C7 121.8(3) . 2 ?
C2 C7 C6 112.1(2) 4 . ?
O1 C1 C6 120.9(2) . . ?
O1 C1 C2 117.7(2) . . ?
C6 C1 C2 121.3(3) . . ?
C2 C3 C4 123.6(2) . . ?
C6 C5 C4 123.1(2) . . ?
C3 C4 C5 116.1(3) . . ?
C3 C4 C8 121.2(2) . . ?
C5 C4 C8 122.7(2) . . ?
C9' C8 C10 125.8(7) . . ?
C9' C8 C4 118.2(7) . . ?
C10 C8 C4 112.9(3) . . ?
C9' C8 C9 38.9(9) . . ?
C10 C8 C9 109.0(4) . . ?
C4 C8 C9 107.7(3) . . ?
C9' C8 C11 68.9(10) . . ?
C10 C8 C11 110.3(4) . . ?
C4 C8 C11 109.1(3) . . ?
C9 C8 C11 107.7(4) . . ?
C9' C8 C11' 110.8(10) . . ?
C10 C8 C11' 65.8(6) . . ?
C4 C8 C11' 109.0(5) . . ?
C9 C8 C11' 141.6(6) . . ?
C11 C8 C11' 49.0(5) . . ?
C9' C8 C10' 103.9(10) . . ?
C10 C8 C10' 37.8(7) . . ?
C4 C8 C10' 111.6(6) . . ?
C9 C8 C10' 74.1(8) . . ?
C11 C8 C10' 136.4(8) . . ?
C11' C8 C10' 102.0(10) . . ?
C12 C11 C8 115.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.058