# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Iain Oswald'
_publ_contact_author_email       IAIN.OSWALD@ED.AC.UK

_publ_section_title              
;
Structural similarities of 2-chlorophenol and
2-methylphenol
;
loop_
_publ_author_name
'Iain Oswald'
'Wilson A. Crichton'

# Attachment 'CPIII.cif'

data_CPIII
_database_code_depnum_ccdc_archive 'CCDC 698227'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
2-Chlorophenol
;

_chemical_name_common            2-Chlorophenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 Cl O'
_chemical_formula_sum            'C6 H5 Cl O'
_chemical_formula_weight         128.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.5826(10)
_cell_length_b                   9.587(3)
_cell_length_c                   10.054(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.19(2)
_cell_angle_gamma                90.00
_cell_volume                     534.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    190
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      19.05

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.585
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.124
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1282
_diffrn_reflns_av_R_equivalents  0.1171
_diffrn_reflns_av_sigmaI/netI    0.1597
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         23.28
_reflns_number_total             397
_reflns_number_gt                194
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0565P)²+0.0000P] 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_number_reflns         397
_refine_ls_number_parameters     37
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1576
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
C1 C -0.1836(9) 0.0928(7) 0.3919(6) 0.033(3) Uiso 1 1 d G . .
C2 C 0.0167(11) 0.1777(7) 0.3857(7) 0.034(3) Uiso 1 1 d GD . .
C3 C 0.1649(8) 0.1583(6) 0.2846(7) 0.037(3) Uiso 1 1 d G . .
H3 H 0.2990 0.2150 0.2804 0.045 Uiso 1 1 calc R . .
C4 C 0.1128(9) 0.0540(7) 0.1899(6) 0.044(3) Uiso 1 1 d G . .
H4 H 0.2119 0.0410 0.1223 0.052 Uiso 1 1 calc R . .
C5 C -0.0876(11) -0.0309(7) 0.1962(7) 0.049(3) Uiso 1 1 d G . .
H5 H -0.1224 -0.1007 0.1328 0.059 Uiso 1 1 calc R . .
C6 C -0.2358(8) -0.0115(6) 0.2972(7) 0.045(3) Uiso 1 1 d G . .
H6 H -0.3698 -0.0683 0.3014 0.054 Uiso 1 1 calc R . .
O7 O -0.3282(13) 0.1134(8) 0.4930(10) 0.052(3) Uani 1 1 d D . .
H71 H -0.28(4) 0.187(17) 0.53(3) 0.077 Uiso 0.50 1 d PD . .
H72 H -0.40(3) 0.037(9) 0.49(3) 0.077 Uiso 0.50 1 d PD . .
Cl8 Cl 0.0925(5) 0.2981(3) 0.5080(4) 0.0585(14) Uani 1 1 d 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
O7 0.044(5) 0.047(9) 0.066(11) 0.002(6) 0.016(6) -0.002(4)
Cl8 0.0623(18) 0.053(3) 0.059(4) -0.0045(18) 0.003(2) -0.0035(16)

_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 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 O7 1.378(8) . ?
C2 C3 1.3900 . ?
C2 Cl8 1.706(5) . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O7 H71 0.821(11) . ?
O7 H72 0.822(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
C2 C1 C6 120.0 . . ?
C2 C1 O7 119.2(5) . . ?
C6 C1 O7 120.8(5) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 Cl8 119.8(4) . . ?
C1 C2 Cl8 120.1(4) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 O7 H71 106(10) . . ?
C1 O7 H72 96(10) . . ?
H71 O7 H72 158(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H72 O7 0.822(11) 2.14(4) 2.913(13) 156(10) 3_456

_diffrn_measured_fraction_theta_max 0.513
_diffrn_reflns_theta_full        23.28
_diffrn_measured_fraction_theta_full 0.513
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.067

# Attachment 'MPCP.cif'

data_MPCP
_database_code_depnum_ccdc_archive 'CCDC 698228'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(0.45)2-METHYLPHENOL:(0.55)2-CHLOROPHENOL
;
_chemical_name_common            (0.45)2-METHYLPHENOL:(0.55)2-CHLOROPHENOL
_chemical_melting_point          ?
_chemical_formula_moiety         0.45(C7H8O)0.55(C6H5OCl)
_chemical_formula_sum            'C6.45 H6.34 Cl0.55 O'
_chemical_formula_weight         119.45

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   P3(2)
_symmetry_space_group_name_Hall  P32

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   16.1628(2)
_cell_length_b                   16.1628(2)
_cell_length_c                   5.9006(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1334.93(3)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.96

_exptl_crystal_description       CYLINDER
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          0.61
_exptl_crystal_size_min          0.61
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             562
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   Multiscan
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33656
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         30.64
_reflns_number_total             5463
_reflns_number_gt                4855
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0593P)²+0.1877P] 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   0.02(5)
_refine_ls_number_reflns         5463
_refine_ls_number_parameters     223
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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
C11 C 0.12010(6) 0.16849(6) 0.52419(19) 0.0271(3) Uani 1 1 d GU A .
C21 C 0.13147(7) 0.23672(7) 0.36478(18) 0.0306(3) Uani 1 1 d GDU . .
C31 C 0.20978(8) 0.32856(7) 0.3772(2) 0.0387(4) Uani 1 1 d GU A .
H31 H 0.2175 0.3752 0.2683 0.046 Uiso 1 1 calc R . .
C41 C 0.27672(7) 0.35218(6) 0.5491(2) 0.0420(4) Uani 1 1 d GU . .
H41 H 0.3302 0.4149 0.5576 0.050 Uiso 1 1 calc R A .
C51 C 0.26536(7) 0.28395(8) 0.7085(2) 0.0369(4) Uani 1 1 d GU A .
H51 H 0.3111 0.3001 0.8260 0.044 Uiso 1 1 calc R . .
C61 C 0.18705(7) 0.19211(7) 0.69608(18) 0.0314(3) Uani 1 1 d GU . .
H61 H 0.1793 0.1455 0.8050 0.038 Uiso 1 1 calc R A .
O71 O 0.04178(9) 0.07817(9) 0.5089(2) 0.0344(3) Uani 1 1 d D . .
H71 H 0.0468(14) 0.0414(13) 0.602(3) 0.035(5) Uiso 1 1 d D . .
C81 C 0.0585(12) 0.2133(11) 0.180(3) 0.030(2) Uani 0.47 1 d PDU A 1
H811 H 0.0667 0.1751 0.0623 0.045 Uiso 0.47 1 calc PR A 1
H821 H 0.0673 0.2727 0.1128 0.045 Uiso 0.47 1 calc PR A 1
H831 H -0.0059 0.1770 0.2438 0.045 Uiso 0.47 1 calc PR A 1
Cl81 Cl 0.0478(3) 0.2072(3) 0.1557(6) 0.0351(5) Uani 0.53 1 d PD A 2
C12 C 0.49515(5) 0.23722(6) 0.04056(19) 0.0276(3) Uani 1 1 d GU B .
C22 C 0.43754(7) 0.23725(7) 0.21542(17) 0.0303(3) Uani 1 1 d GDU . .
C32 C 0.34158(7) 0.16735(8) 0.22331(19) 0.0364(4) Uani 1 1 d GU B .
H32 H 0.3022 0.1674 0.3428 0.044 Uiso 1 1 calc R . .
C42 C 0.30322(5) 0.09741(8) 0.0563(2) 0.0402(4) Uani 1 1 d GU . .
H42 H 0.2376 0.0496 0.0617 0.048 Uiso 1 1 calc R B .
C52 C 0.36082(7) 0.09738(7) -0.1185(2) 0.0397(4) Uani 1 1 d GU B .
H52 H 0.3346 0.0496 -0.2327 0.048 Uiso 1 1 calc R . .
C62 C 0.45679(7) 0.16728(7) -0.12643(18) 0.0331(3) Uani 1 1 d GU . .
H62 H 0.4962 0.1673 -0.2459 0.040 Uiso 1 1 calc R B .
O72 O 0.58959(8) 0.30858(8) 0.0340(2) 0.0311(2) Uani 1 1 d D . .
H72 H 0.6204(14) 0.2956(15) -0.063(3) 0.031(5) Uiso 1 1 d D . .
C82 C 0.4786(13) 0.3205(9) 0.379(2) 0.066(5) Uani 0.37 1 d PDU B 1
H812 H 0.4266 0.3208 0.4632 0.100 Uiso 0.37 1 calc PR B 1
H822 H 0.5141 0.3803 0.2940 0.100 Uiso 0.37 1 calc PR B 1
H832 H 0.5218 0.3142 0.4848 0.100 Uiso 0.37 1 calc PR B 1
Cl82 Cl 0.48671(12) 0.32207(8) 0.4232(2) 0.0331(2) Uani 0.63 1 d PD B 2
C13 C 0.39238(7) -0.16507(6) 0.5298(2) 0.0309(3) Uani 1 1 d GU C .
C23 C 0.37884(7) -0.11707(8) 0.35106(19) 0.0354(3) Uani 1 1 d GDU . .
C33 C 0.43694(9) -0.01868(8) 0.3305(2) 0.0434(4) Uani 1 1 d GU C .
H33 H 0.4277 0.0141 0.2083 0.052 Uiso 1 1 calc R . .
C43 C 0.50857(9) 0.03171(6) 0.4887(3) 0.0469(5) Uani 1 1 d GU . .
H43 H 0.5483 0.0990 0.4746 0.056 Uiso 1 1 calc R C .
C53 C 0.52210(8) -0.01628(8) 0.6674(2) 0.0456(4) Uani 1 1 d GU C .
H53 H 0.5711 0.0182 0.7756 0.055 Uiso 1 1 calc R . .
C63 C 0.46401(8) -0.11467(8) 0.68804(19) 0.0376(4) Uani 1 1 d GU . .
H63 H 0.4733 -0.1475 0.8102 0.045 Uiso 1 1 calc R C .
O73 O 0.33535(9) -0.26295(8) 0.5466(2) 0.0334(3) Uani 1 1 d D . .
H73 H 0.3555(17) -0.2843(16) 0.649(3) 0.044(6) Uiso 1 1 d D . .
C83 C 0.2992(7) -0.1696(9) 0.1808(19) 0.046(2) Uani 0.50 1 d PDU C 1
H813 H 0.3205 -0.1973 0.0626 0.069 Uiso 0.50 1 calc PR C 1
H823 H 0.2824 -0.1248 0.1118 0.069 Uiso 0.50 1 calc PR C 1
H833 H 0.2431 -0.2206 0.2578 0.069 Uiso 0.50 1 calc PR C 1
Cl83 Cl 0.28748(19) -0.1808(2) 0.1632(4) 0.0403(5) Uani 0.50 1 d PD C 2

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
C11 0.0233(6) 0.0295(7) 0.0300(7) -0.0022(6) 0.0016(5) 0.0144(6)
C21 0.0290(7) 0.0345(8) 0.0316(7) 0.0010(6) 0.0021(6) 0.0183(6)
C31 0.0362(9) 0.0344(8) 0.0441(9) 0.0052(7) 0.0013(7) 0.0166(7)
C41 0.0368(9) 0.0285(8) 0.0534(11) -0.0018(7) -0.0032(8) 0.0108(7)
C51 0.0307(8) 0.0363(8) 0.0415(9) -0.0066(7) -0.0072(7) 0.0151(7)
C61 0.0296(7) 0.0338(8) 0.0327(8) 0.0001(6) -0.0009(6) 0.0174(6)
O71 0.0276(5) 0.0303(6) 0.0400(6) 0.0039(5) -0.0059(4) 0.0104(4)
C81 0.032(4) 0.024(3) 0.032(4) 0.002(2) -0.004(2) 0.012(3)
Cl81 0.0319(8) 0.0474(11) 0.0278(7) 0.0030(6) -0.0054(5) 0.0212(8)
C12 0.0266(7) 0.0273(7) 0.0281(7) 0.0028(5) -0.0003(5) 0.0129(6)
C22 0.0343(8) 0.0307(7) 0.0283(7) 0.0050(6) 0.0023(6) 0.0180(6)
C32 0.0325(8) 0.0416(9) 0.0364(8) 0.0132(7) 0.0075(6) 0.0195(7)
C42 0.0267(8) 0.0398(9) 0.0460(9) 0.0121(7) -0.0027(6) 0.0106(7)
C52 0.0338(8) 0.0374(9) 0.0389(9) 0.0002(7) -0.0078(7) 0.0111(7)
C62 0.0319(8) 0.0336(8) 0.0308(8) -0.0001(6) -0.0007(6) 0.0142(7)
O72 0.0262(5) 0.0294(5) 0.0320(6) -0.0043(4) 0.0031(4) 0.0096(4)
C82 0.055(5) 0.086(7) 0.034(6) -0.018(4) -0.004(4) 0.017(4)
Cl82 0.0421(5) 0.0365(4) 0.0238(5) -0.0013(3) 0.0050(4) 0.0220(4)
C13 0.0299(7) 0.0294(7) 0.0357(8) 0.0009(6) 0.0061(6) 0.0165(6)
C23 0.0328(8) 0.0382(8) 0.0380(8) 0.0045(7) 0.0052(6) 0.0199(7)
C33 0.0470(10) 0.0385(9) 0.0486(10) 0.0082(8) 0.0187(8) 0.0244(8)
C43 0.0494(10) 0.0342(9) 0.0553(12) -0.0001(8) 0.0200(9) 0.0195(8)
C53 0.0401(9) 0.0384(9) 0.0506(10) -0.0146(8) 0.0032(8) 0.0137(8)
C63 0.0352(8) 0.0343(8) 0.0418(9) -0.0048(7) 0.0026(7) 0.0164(7)
O73 0.0337(6) 0.0274(5) 0.0320(6) 0.0002(4) -0.0067(5) 0.0100(5)
C83 0.046(4) 0.048(4) 0.054(5) 0.001(3) 0.013(3) 0.031(3)
Cl83 0.0365(7) 0.0526(10) 0.0302(6) 0.0100(6) -0.0074(5) 0.0212(6)

_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
C11 O71 1.3762(14) . ?
C11 C21 1.3900 . ?
C11 C61 1.3900 . ?
C21 C31 1.3900 . ?
C21 C81 1.511(8) . ?
C21 Cl81 1.712(2) . ?
C31 C41 1.3900 . ?
C31 H31 0.9500 . ?
C41 C51 1.3900 . ?
C41 H41 0.9500 . ?
C51 C61 1.3900 . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
O71 H71 0.845(9) . ?
C81 H811 0.9800 . ?
C81 H821 0.9800 . ?
C81 H831 0.9800 . ?
C12 O72 1.3789(13) . ?
C12 C22 1.3900 . ?
C12 C62 1.3900 . ?
C22 C32 1.3900 . ?
C22 C82 1.512(8) . ?
C22 Cl82 1.7103(15) . ?
C32 C42 1.3900 . ?
C32 H32 0.9500 . ?
C42 C52 1.3900 . ?
C42 H42 0.9500 . ?
C52 C62 1.3900 . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
O72 H72 0.849(9) . ?
C82 H812 0.9800 . ?
C82 H822 0.9800 . ?
C82 H832 0.9800 . ?
C13 O73 1.3799(14) . ?
C13 C23 1.3900 . ?
C13 C63 1.3900 . ?
C23 C33 1.3900 . ?
C23 C83 1.514(8) . ?
C23 Cl83 1.718(2) . ?
C33 C43 1.3900 . ?
C33 H33 0.9500 . ?
C43 C53 1.3900 . ?
C43 H43 0.9500 . ?
C53 C63 1.3900 . ?
C53 H53 0.9500 . ?
C63 H63 0.9500 . ?
O73 H73 0.837(9) . ?
C83 H813 0.9800 . ?
C83 H823 0.9800 . ?
C83 H833 0.9800 . ?

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
O71 C11 C21 118.94(8) . . ?
O71 C11 C61 121.06(8) . . ?
C21 C11 C61 120.0 . . ?
C11 C21 C31 120.0 . . ?
C11 C21 C81 120.9(6) . . ?
C31 C21 C81 119.1(6) . . ?
C11 C21 Cl81 119.57(15) . . ?
C31 C21 Cl81 120.42(15) . . ?
C81 C21 Cl81 1.5(7) . . ?
C41 C31 C21 120.0 . . ?
C41 C31 H31 120.0 . . ?
C21 C31 H31 120.0 . . ?
C51 C41 C31 120.0 . . ?
C51 C41 H41 120.0 . . ?
C31 C41 H41 120.0 . . ?
C61 C51 C41 120.0 . . ?
C61 C51 H51 120.0 . . ?
C41 C51 H51 120.0 . . ?
C51 C61 C11 120.0 . . ?
C51 C61 H61 120.0 . . ?
C11 C61 H61 120.0 . . ?
C11 O71 H71 110.1(14) . . ?
C21 C81 H811 109.5 . . ?
C21 C81 H821 109.5 . . ?
C21 C81 H831 109.5 . . ?
O72 C12 C22 118.83(8) . . ?
O72 C12 C62 121.16(8) . . ?
C22 C12 C62 120.0 . . ?
C12 C22 C32 120.0 . . ?
C12 C22 C82 118.5(7) . . ?
C32 C22 C82 121.1(7) . . ?
C12 C22 Cl82 119.32(8) . . ?
C32 C22 Cl82 120.66(8) . . ?
C82 C22 Cl82 7.5(7) . . ?
C22 C32 C42 120.0 . . ?
C22 C32 H32 120.0 . . ?
C42 C32 H32 120.0 . . ?
C52 C42 C32 120.0 . . ?
C52 C42 H42 120.0 . . ?
C32 C42 H42 120.0 . . ?
C42 C52 C62 120.0 . . ?
C42 C52 H52 120.0 . . ?
C62 C52 H52 120.0 . . ?
C52 C62 C12 120.0 . . ?
C52 C62 H62 120.0 . . ?
C12 C62 H62 120.0 . . ?
C12 O72 H72 110.6(15) . . ?
C22 C82 H812 109.5 . . ?
C22 C82 H822 109.5 . . ?
C22 C82 H832 109.5 . . ?
O73 C13 C23 119.54(9) . . ?
O73 C13 C63 120.45(9) . . ?
C23 C13 C63 120.0 . . ?
C33 C23 C13 120.0 . . ?
C33 C23 C83 118.8(5) . . ?
C13 C23 C83 121.2(5) . . ?
C33 C23 Cl83 121.08(11) . . ?
C13 C23 Cl83 118.89(11) . . ?
C83 C23 Cl83 2.3(6) . . ?
C23 C33 C43 120.0 . . ?
C23 C33 H33 120.0 . . ?
C43 C33 H33 120.0 . . ?
C53 C43 C33 120.0 . . ?
C53 C43 H43 120.0 . . ?
C33 C43 H43 120.0 . . ?
C43 C53 C63 120.0 . . ?
C43 C53 H53 120.0 . . ?
C63 C53 H53 120.0 . . ?
C53 C63 C13 120.0 . . ?
C53 C63 H63 120.0 . . ?
C13 C63 H63 120.0 . . ?
C13 O73 H73 110.5(17) . . ?
C23 C83 H813 109.5 . . ?
C23 C83 H823 109.5 . . ?
C23 C83 H833 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.64
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050

# Attachment 'MPI.CIF'

data_MPI
_database_code_depnum_ccdc_archive 'CCDC 698229'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-methylphenol
;
_chemical_name_common            2-methylphenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O'
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   P3(2)
_symmetry_space_group_name_Hall  'P 32'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   16.4153(2)
_cell_length_b                   16.4153(2)
_cell_length_c                   5.7931(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1351.88(5)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6079
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14653
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         30.00
_reflns_number_total             2622
_reflns_number_gt                2538
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0742P)²+0.0000P] 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   10(10)
_refine_ls_number_reflns         2622
_refine_ls_number_parameters     233
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.11895(13) 0.16725(14) 0.5049(3) 0.0219(3) Uani 1 1 d . . .
C21 C 0.12625(14) 0.23789(15) 0.3578(4) 0.0243(4) Uani 1 1 d . . .
C31 C 0.20067(16) 0.32918(15) 0.3955(4) 0.0310(4) Uani 1 1 d . . .
H31 H 0.2074 0.3785 0.2974 0.037 Uiso 1 1 calc R . .
C41 C 0.26515(16) 0.34961(16) 0.5731(4) 0.0323(5) Uani 1 1 d . . .
H41 H 0.3154 0.4121 0.5949 0.039 Uiso 1 1 calc R . .
C51 C 0.25568(16) 0.27805(17) 0.7184(4) 0.0283(4) Uani 1 1 d . . .
H51 H 0.2991 0.2916 0.8409 0.034 Uiso 1 1 calc R . .
C61 C 0.18264(14) 0.18676(14) 0.6841(4) 0.0242(4) Uani 1 1 d . . .
H61 H 0.1761 0.1376 0.7828 0.029 Uiso 1 1 calc R . .
O71 O 0.04571(11) 0.07696(10) 0.4683(3) 0.0285(3) Uani 1 1 d D . .
H71 H 0.045(2) 0.0386(17) 0.560(5) 0.033(8) Uiso 1 1 d D . .
C81 C 0.05686(15) 0.21609(16) 0.1666(4) 0.0293(4) Uani 1 1 d . . .
H811 H 0.0644 0.1770 0.0505 0.044 Uiso 1 1 calc R . .
H821 H 0.0679 0.2749 0.0951 0.044 Uiso 1 1 calc R . .
H831 H -0.0071 0.1822 0.2292 0.044 Uiso 1 1 calc R . .
C12 C 0.49588(14) 0.23219(14) 0.0479(3) 0.0221(3) Uani 1 1 d . . .
C22 C 0.43711(15) 0.23395(15) 0.2196(3) 0.0250(4) Uani 1 1 d . . .
C32 C 0.34249(16) 0.16428(17) 0.2116(4) 0.0307(4) Uani 1 1 d . . .
H32 H 0.3006 0.1642 0.3247 0.037 Uiso 1 1 calc R . .
C42 C 0.30795(15) 0.09494(17) 0.0425(4) 0.0332(5) Uani 1 1 d . . .
H42 H 0.2432 0.0482 0.0411 0.040 Uiso 1 1 calc R . .
C52 C 0.36822(16) 0.09398(16) -0.1247(4) 0.0311(4) Uani 1 1 d . . .
H52 H 0.3452 0.0462 -0.2394 0.037 Uiso 1 1 calc R . .
C62 C 0.46228(15) 0.16334(14) -0.1225(3) 0.0253(4) Uani 1 1 d . . .
H62 H 0.5038 0.1638 -0.2374 0.030 Uiso 1 1 calc R . .
O72 O 0.58909(10) 0.30268(11) 0.0511(3) 0.0262(3) Uani 1 1 d D . .
H72 H 0.6217(17) 0.295(2) -0.043(4) 0.030(7) Uiso 1 1 d D . .
C82 C 0.47562(17) 0.30725(17) 0.4073(4) 0.0309(4) Uani 1 1 d . . .
H812 H 0.4235 0.3030 0.4994 0.046 Uiso 1 1 calc R . .
H822 H 0.5108 0.3699 0.3378 0.046 Uiso 1 1 calc R . .
H832 H 0.5176 0.2965 0.5070 0.046 Uiso 1 1 calc R . .
C13 C 0.40198(14) -0.16408(14) 0.5298(4) 0.0248(4) Uani 1 1 d . . .
C23 C 0.38985(15) -0.11351(15) 0.3543(4) 0.0277(4) Uani 1 1 d . . .
C33 C 0.45191(19) -0.01624(17) 0.3472(4) 0.0354(5) Uani 1 1 d . . .
H33 H 0.4448 0.0202 0.2300 0.042 Uiso 1 1 calc R . .
C43 C 0.52357(18) 0.02787(16) 0.5084(5) 0.0374(5) Uani 1 1 d . . .
H43 H 0.5659 0.0937 0.4981 0.045 Uiso 1 1 calc R . .
C53 C 0.53345(16) -0.02358(17) 0.6839(4) 0.0347(5) Uani 1 1 d . . .
H53 H 0.5819 0.0069 0.7955 0.042 Uiso 1 1 calc R . .
C63 C 0.47222(16) -0.12034(16) 0.6966(4) 0.0291(4) Uani 1 1 d . . .
H63 H 0.4782 -0.1562 0.8174 0.035 Uiso 1 1 calc R . .
O73 O 0.34215(11) -0.26067(10) 0.5396(2) 0.0263(3) Uani 1 1 d D . .
H73 H 0.352(2) -0.286(2) 0.651(4) 0.038(8) Uiso 1 1 d D . .
C83 C 0.31346(17) -0.16157(18) 0.1774(4) 0.0342(5) Uani 1 1 d . . .
H813 H 0.3272 -0.2021 0.0803 0.051 Uiso 1 1 calc R . .
H823 H 0.3103 -0.1142 0.0809 0.051 Uiso 1 1 calc R . .
H833 H 0.2530 -0.1998 0.2555 0.051 Uiso 1 1 calc R . .

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
C11 0.0177(8) 0.0214(8) 0.0265(9) -0.0015(7) 0.0013(6) 0.0097(7)
C21 0.0215(8) 0.0251(9) 0.0267(9) 0.0001(7) 0.0008(7) 0.0120(8)
C31 0.0284(10) 0.0232(9) 0.0356(11) 0.0037(8) -0.0008(8) 0.0087(8)
C41 0.0258(9) 0.0239(9) 0.0393(12) -0.0033(8) -0.0026(8) 0.0064(8)
C51 0.0254(9) 0.0319(10) 0.0279(9) -0.0052(7) -0.0043(7) 0.0145(8)
C61 0.0230(8) 0.0252(9) 0.0267(9) -0.0002(7) -0.0001(7) 0.0139(7)
O71 0.0242(7) 0.0209(7) 0.0363(8) 0.0030(6) -0.0066(6) 0.0081(6)
C81 0.0276(10) 0.0299(10) 0.0302(10) 0.0022(8) -0.0030(7) 0.0142(8)
C12 0.0216(8) 0.0206(8) 0.0237(9) 0.0029(7) 0.0007(7) 0.0102(7)
C22 0.0275(9) 0.0266(9) 0.0237(9) 0.0042(7) 0.0032(7) 0.0156(8)
C32 0.0263(10) 0.0357(11) 0.0313(10) 0.0107(8) 0.0068(8) 0.0165(9)
C42 0.0213(9) 0.0319(11) 0.0380(12) 0.0074(9) -0.0010(8) 0.0072(8)
C52 0.0288(10) 0.0240(9) 0.0346(11) 0.0003(8) -0.0080(8) 0.0087(8)
C62 0.0254(9) 0.0243(9) 0.0253(9) -0.0004(7) -0.0005(7) 0.0117(8)
O72 0.0223(7) 0.0230(6) 0.0294(7) -0.0046(5) 0.0023(5) 0.0083(6)
C82 0.0349(11) 0.0355(11) 0.0268(10) -0.0020(8) 0.0042(8) 0.0210(9)
C13 0.0241(9) 0.0233(9) 0.0274(9) 0.0012(7) 0.0060(7) 0.0120(7)
C23 0.0279(10) 0.0293(10) 0.0290(10) 0.0026(8) 0.0055(8) 0.0166(9)
C33 0.0383(12) 0.0298(10) 0.0408(12) 0.0085(9) 0.0169(10) 0.0192(10)
C43 0.0373(12) 0.0235(10) 0.0485(14) -0.0025(9) 0.0159(10) 0.0131(9)
C53 0.0281(10) 0.0295(10) 0.0405(12) -0.0092(9) 0.0039(9) 0.0098(9)
C63 0.0273(10) 0.0277(10) 0.0318(10) -0.0026(8) 0.0032(8) 0.0135(8)
O73 0.0248(7) 0.0213(7) 0.0266(7) 0.0012(5) -0.0042(6) 0.0069(6)
C83 0.0332(11) 0.0400(12) 0.0307(10) 0.0071(9) 0.0011(8) 0.0193(10)

_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
C11 O71 1.380(2) . ?
C11 C61 1.392(3) . ?
C11 C21 1.395(3) . ?
C21 C31 1.398(3) . ?
C21 C81 1.498(3) . ?
C31 C41 1.392(3) . ?
C31 H31 0.9500 . ?
C41 C51 1.389(3) . ?
C41 H41 0.9500 . ?
C51 C61 1.388(3) . ?
C51 H51 0.9500 . ?
C61 H61 0.9500 . ?
O71 H71 0.8200(10) . ?
C81 H811 0.9800 . ?
C81 H821 0.9800 . ?
C81 H831 0.9800 . ?
C12 O72 1.382(2) . ?
C12 C62 1.390(3) . ?
C12 C22 1.396(3) . ?
C22 C32 1.395(3) . ?
C22 C82 1.507(3) . ?
C32 C42 1.390(4) . ?
C32 H32 0.9500 . ?
C42 C52 1.390(4) . ?
C42 H42 0.9500 . ?
C52 C62 1.387(3) . ?
C52 H52 0.9500 . ?
C62 H62 0.9500 . ?
O72 H72 0.8200(11) . ?
C82 H812 0.9800 . ?
C82 H822 0.9800 . ?
C82 H832 0.9800 . ?
C13 O73 1.387(2) . ?
C13 C23 1.388(3) . ?
C13 C63 1.397(3) . ?
C23 C33 1.401(3) . ?
C23 C83 1.502(3) . ?
C33 C43 1.389(4) . ?
C33 H33 0.9500 . ?
C43 C53 1.382(4) . ?
C43 H43 0.9500 . ?
C53 C63 1.394(3) . ?
C53 H53 0.9500 . ?
C63 H63 0.9500 . ?
O73 H73 0.8200(10) . ?
C83 H813 0.9800 . ?
C83 H823 0.9800 . ?
C83 H833 0.9800 . ?

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
O71 C11 C61 120.82(18) . . ?
O71 C11 C21 117.72(17) . . ?
C61 C11 C21 121.46(18) . . ?
C11 C21 C31 117.45(19) . . ?
C11 C21 C81 120.94(18) . . ?
C31 C21 C81 121.61(19) . . ?
C41 C31 C21 121.7(2) . . ?
C41 C31 H31 119.1 . . ?
C21 C31 H31 119.1 . . ?
C51 C41 C31 119.6(2) . . ?
C51 C41 H41 120.2 . . ?
C31 C41 H41 120.2 . . ?
C61 C51 C41 119.8(2) . . ?
C61 C51 H51 120.1 . . ?
C41 C51 H51 120.1 . . ?
C51 C61 C11 119.94(19) . . ?
C51 C61 H61 120.0 . . ?
C11 C61 H61 120.0 . . ?
C11 O71 H71 113(2) . . ?
C21 C81 H811 109.5 . . ?
C21 C81 H821 109.5 . . ?
H811 C81 H821 109.5 . . ?
C21 C81 H831 109.5 . . ?
H811 C81 H831 109.5 . . ?
H821 C81 H831 109.5 . . ?
O72 C12 C62 120.88(18) . . ?
O72 C12 C22 117.42(18) . . ?
C62 C12 C22 121.69(19) . . ?
C32 C22 C12 117.2(2) . . ?
C32 C22 C82 121.95(19) . . ?
C12 C22 C82 120.83(19) . . ?
C42 C32 C22 121.7(2) . . ?
C42 C32 H32 119.1 . . ?
C22 C32 H32 119.1 . . ?
C52 C42 C32 119.9(2) . . ?
C52 C42 H42 120.0 . . ?
C32 C42 H42 120.0 . . ?
C62 C52 C42 119.4(2) . . ?
C62 C52 H52 120.3 . . ?
C42 C52 H52 120.3 . . ?
C52 C62 C12 120.0(2) . . ?
C52 C62 H62 120.0 . . ?
C12 C62 H62 120.0 . . ?
C12 O72 H72 113(2) . . ?
C22 C82 H812 109.5 . . ?
C22 C82 H822 109.5 . . ?
H812 C82 H822 109.5 . . ?
C22 C82 H832 109.5 . . ?
H812 C82 H832 109.5 . . ?
H822 C82 H832 109.5 . . ?
O73 C13 C23 118.81(19) . . ?
O73 C13 C63 119.34(18) . . ?
C23 C13 C63 121.84(19) . . ?
C13 C23 C33 117.6(2) . . ?
C13 C23 C83 121.15(19) . . ?
C33 C23 C83 121.3(2) . . ?
C43 C33 C23 121.2(2) . . ?
C43 C33 H33 119.4 . . ?
C23 C33 H33 119.4 . . ?
C53 C43 C33 120.2(2) . . ?
C53 C43 H43 119.9 . . ?
C33 C43 H43 119.9 . . ?
C43 C53 C63 119.8(2) . . ?
C43 C53 H53 120.1 . . ?
C63 C53 H53 120.1 . . ?
C53 C63 C13 119.3(2) . . ?
C53 C63 H63 120.4 . . ?
C13 C63 H63 120.4 . . ?
C13 O73 H73 114(3) . . ?
C23 C83 H813 109.5 . . ?
C23 C83 H823 109.5 . . ?
H813 C83 H823 109.5 . . ?
C23 C83 H833 109.5 . . ?
H813 C83 H833 109.5 . . ?
H823 C83 H833 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054

# Attachment 'MPII.cif'

data_MPII
_database_code_depnum_ccdc_archive 'CCDC 698230'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-methylphenol
;
_chemical_name_common            2-methylphenol
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O'
_chemical_formula_sum            'C7 H8 O'
_chemical_formula_weight         108.13

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           Monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   5.9637(4)
_cell_length_b                   4.7006(3)
_cell_length_c                   19.769(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.792(10)
_cell_angle_gamma                90.00
_cell_volume                     553.53(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    633
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      21.40

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.327
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2367
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         23.25
_reflns_number_total             307
_reflns_number_gt                217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker-Nonius Apex II'
_computing_cell_refinement       'Bruker-Nonius Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0762P)²+1.8389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         307
_refine_ls_number_parameters     17
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0870
_refine_ls_wR_factor_ref         0.2256
_refine_ls_wR_factor_gt          0.1957
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4767(4) 0.5171(6) 0.8262(3) 0.0303(19) Uiso 1 1 d G . .
C2 C 0.5026(5) 0.6422(7) 0.8898(3) 0.034(2) Uiso 1 1 d G . .
C3 C 0.6836(7) 0.5678(9) 0.9331(3) 0.048(2) Uiso 1 1 d G . .
H3 H 0.7009 0.6515 0.9757 0.057 Uiso 1 1 calc R . .
C4 C 0.8387(7) 0.3683(10) 0.9129(4) 0.049(2) Uiso 1 1 d G . .
H4 H 0.9598 0.3185 0.9419 0.059 Uiso 1 1 calc R . .
C5 C 0.8129(6) 0.2432(9) 0.8493(4) 0.042(2) Uiso 1 1 d G . .
H5 H 0.9167 0.1097 0.8357 0.050 Uiso 1 1 calc R . .
C6 C 0.6319(6) 0.3176(8) 0.8059(3) 0.041(2) Uiso 1 1 d G . .
H6 H 0.6146 0.2339 0.7634 0.050 Uiso 1 1 calc R . .
O7 O 0.2985(6) 0.5903(8) 0.7840(4) 0.0398(17) Uiso 1 1 d G . .
H7 H 0.2248 0.4478 0.7741 0.060 Uiso 1 1 calc R . .
C8 C 0.3307(8) 0.8567(11) 0.9117(4) 0.046(2) Uiso 1 1 d G . .
H81 H 0.3641 1.0401 0.8933 0.069 Uiso 1 1 calc R . .
H82 H 0.3355 0.8676 0.9602 0.069 Uiso 1 1 calc R . .
H83 H 0.1836 0.7982 0.8954 0.069 Uiso 1 1 calc R . .

_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 O7 1.3621 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 C8 1.5158 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
O7 H7 0.8200 . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 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
O7 C1 C2 119.7 . . ?
O7 C1 C6 120.3 . . ?
C2 C1 C6 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 C8 119.5 . . ?
C3 C2 C8 120.5 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 O7 H7 109.5 . . ?
C2 C8 H81 109.5 . . ?
C2 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C2 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O7 0.82 2.04 2.756(8) 146.1 2_546

_diffrn_measured_fraction_theta_max 0.383
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.383
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.052


