# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003


data_global

_publ_contact_author_email       C.R.PULHAM@ED.AC.UK

_publ_contact_author_name        'Dr Colin Pulham'
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_publ_contact_author_address     
;
Chemistry
University of Edinburgh
King's Buildings
West Mains Road
Edinburgh
EH9 3JJ
UNITED KINGDOM
;

_publ_section_title              
;
Pressure-induced formation of a solvate of
paracetamol
;

loop_
_publ_author_name
'Colin Pulham'
'David Robert Allan'
'William David'
'Alice Dawson'
'Francesca P. A. Fabbiani'
;
P.A.McGregor
;
'Iain D. H. Oswald'
'Simon Parsons'

data_compound_1
_database_code_depnum_ccdc_archive 'CCDC 218910'
_chemical_name_common            'paracetamol monomethanolate'

_chemical_name_systematic        # IUPAC name, in full
;
paracetamol monomethanolate
;

_chemical_melting_point          ?

# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'
_refine_ls_matrix_type           full

# choose from 'heavy, direct, difmap, geom'
_atom_sites_solution_primary     direct

# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'
_refine_ls_hydrogen_treatment    noref

#****************************************************************************
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics    
;
CAMERON (Watkin et al 1996)
;
#=============================================================

_cell_length_a                   7.630(2)
_cell_angle_alpha                90
_cell_length_b                   17.209(3)
_cell_angle_beta                 115.52(3)
_cell_length_c                   7.3710(11)
_cell_angle_gamma                90
_cell_volume                     873.4(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '

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

_chemical_absolute_configuration .

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_IV_Table_2.2B
'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_IV_Table_2.2B
'N   ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B

_cell_formula_units_Z            4
_chemical_formula_sum            ' C9 H13 N1 O3 '
_chemical_formula_moiety         ' C9 H13 N1 O3 '
_chemical_compound_source        
;
?
;
_chemical_formula_weight         183.21

_cell_measurement_reflns_used    285
_cell_measurement_theta_min      4
_cell_measurement_theta_max      18
_cell_measurement_temperature    293

_exptl_crystal_description       ' colourless '
_exptl_crystal_colour            ' block '
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             392.000
_exptl_absorpt_coefficient_mu    0.105
# Sheldrick geometric definitions 0.98 0.99

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'

_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
SMART (Siemens, 1993)
;
_computing_data_reduction        
;
SAINT (Siemens ,1995)
;
_computing_cell_refinement       
;
SAINT (Siemens ,1995)
;
_computing_structure_solution    DASH

_diffrn_measurement_method       'omega scans'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'

_exptl_absorpt_correction_T_min  0.2895
_exptl_absorpt_correction_T_max  1.0000

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      293
_diffrn_reflns_number            801
_reflns_number_total             223
_diffrn_reflns_av_R_equivalents  0.05
# Number of reflections with Friedels Law is 223
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 613

_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         20.843
_diffrn_measured_fraction_theta_max 0.244

_diffrn_reflns_theta_full        15.632
_diffrn_measured_fraction_theta_full 0.339

_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -4
_reflns_limit_h_max              1
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_refine_diff_density_min         -0.43
_refine_diff_density_max         0.33

_refine_ls_number_reflns         172
_refine_ls_number_restraints     2
_refine_ls_number_parameters     14

#_refine_ls_R_factor_ref 0.1848
_refine_ls_wR_factor_ref         0.2161
_refine_ls_goodness_of_fit_ref   0.9312

#_reflns_number_all 172
_refine_ls_R_factor_all          0.1848
_refine_ls_wR_factor_all         0.2161

# No actual I/u(I) cutoff was used for refinement. The
# threshold below is used for "_gt" information ONLY:
_reflns_threshold_expression     I>2.00u(I)
_reflns_number_gt                118
_refine_ls_R_factor_gt           0.1347
_refine_ls_wR_factor_gt          0.1845

_refine_ls_shift/su_max          0.000032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2
A~i~ are:
9.45 10.7 2.51
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

## -------------------REFERENCES ----------------------##
## Insert your own references - in alphabetic order
_publ_section_references         
;

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Siemens Industrial Automation, Inc (1993)
SMART: Area-Detector Software Package; Madison, WI.

Siemens Industrial Automation, Inc (1995).
SAINT: Area-Detector Integration Software.; Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Sheldrick, G.M. (1986). SHELXS86. Program for the solution of
crystal structures. Univ. of Gottingen, Federal Republic of Germany.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper
R.I. (2001) CRYSTALS
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;

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

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
_atom_site_attached_hydrogens
O1 O 1.418(4) 0.2012(8) 0.453(2) 0.062(4) 1.0000 Uiso G .
H11 H 1.482(4) 0.1617(9) 0.447(3) 0.049(4) 1.0000 Uiso G .
O2 O 0.619(4) 0.0236(8) -0.131(2) 0.062(4) 1.0000 Uiso GD .
N3 N 0.626(4) 0.1452(7) -0.007(2) 0.062(4) 1.0000 Uiso GD .
C4 C 0.829(4) 0.1566(6) 0.106(2) 0.062(4) 1.0000 Uiso GD .
C5 C 0.971(4) 0.1085(6) 0.094(2) 0.062(4) 1.0000 Uiso GD .
C6 C 1.167(4) 0.1244(7) 0.212(2) 0.062(4) 1.0000 Uiso G .
C7 C 1.223(4) 0.1874(6) 0.343(2) 0.062(4) 1.0000 Uiso G .
C8 C 1.080(4) 0.2343(6) 0.358(3) 0.062(4) 1.0000 Uiso G .
C9 C 0.886(4) 0.2188(7) 0.241(3) 0.062(4) 1.0000 Uiso G .
C10 C 0.534(4) 0.0831(8) -0.118(2) 0.062(4) 1.0000 Uiso GD .
C11 C 0.316(4) 0.091(1) -0.227(3) 0.062(4) 1.0000 Uiso G .
O13 O 0.351(7) -0.0905(13) -0.448(4) 0.062(4) 1.0000 Uiso G .
C12 C 0.157(7) -0.078(2) -0.566(6) 0.062(4) 1.0000 Uiso G .
H51 H 0.9307 0.0630 -0.0005 0.073(4) 1.0000 Uiso . .
H61 H 1.2667 0.0898 0.1991 0.073(4) 1.0000 Uiso . .
H81 H 1.1207 0.2785 0.4548 0.073(4) 1.0000 Uiso . .
H91 H 0.7856 0.2525 0.2543 0.073(4) 1.0000 Uiso . .
H111 H 0.2747 0.1438 -0.1956 0.073(4) 1.0000 Uiso . .
H112 H 0.2716 0.0866 -0.3739 0.073(4) 1.0000 Uiso . .
H113 H 0.2518 0.0500 -0.1792 0.073(4) 1.0000 Uiso . .
H31 H 0.5405 0.1895 -0.0019 0.074(4) 1.0000 Uiso . .
H131 H 0.4337 -0.0522 -0.3521 0.039(4) 1.0000 Uiso . .
H121 H 0.1026 -0.1282 -0.6557 0.075(4) 1.0000 Uiso . .
H122 H 0.1286 -0.0339 -0.6528 0.075(4) 1.0000 Uiso . .
H123 H 0.0850 -0.0765 -0.4785 0.075(4) 1.0000 Uiso . .
_refine_ls_extinction_method     None
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
O1 . C7 . 1.3735 yes
O1 . H11 . 0.85000 no
O2 . C10 . 1.23881 yes
N3 . H31 . 1.015 no
N3 . C10 . 1.3458 yes
N3 . C4 . 1.4208 yes
C4 . C9 . 1.3952 yes
C4 . C5 . 1.3995 yes
C5 . H51 . 1.006 no
C5 . C6 . 1.3918 yes
C6 . H61 . 1.003 no
C6 . C7 . 1.3913 yes
C7 . C8 . 1.3963 yes
C8 . H81 . 0.994 no
C8 . C9 . 1.3869 yes
C9 . H91 . 0.997 no
C10 . C11 . 1.5077 yes
C11 . H113 . 1.003 no
C11 . H112 . 0.987 no
C11 . H111 . 1.023 no
O13 . H131 . 0.974 no
O13 . C12 . 1.3717 yes
C12 . H123 . 1.016 no
C12 . H122 . 0.960 no
C12 . H121 . 1.050 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
C7 . O1 . H11 . 109.474 no
H31 . N3 . C10 . 116.277 no
H31 . N3 . C4 . 115.362 no
C10 . N3 . C4 . 128.353 yes
C9 . C4 . C5 . 119.15 yes
C9 . C4 . N3 . 116.77 yes
C5 . C4 . N3 . 124.05 yes
H51 . C5 . C6 . 120.872 no
H51 . C5 . C4 . 119.304 no
C6 . C5 . C4 . 119.823 yes
H61 . C6 . C7 . 120.681 no
H61 . C6 . C5 . 118.513 no
C7 . C6 . C5 . 120.80 yes
C8 . C7 . O1 . 122.37 yes
C8 . C7 . C6 . 119.35 yes
O1 . C7 . C6 . 118.276 yes
H81 . C8 . C9 . 120.811 no
H81 . C8 . C7 . 119.196 no
C9 . C8 . C7 . 119.991 yes
H91 . C9 . C8 . 119.086 no
H91 . C9 . C4 . 120.062 no
C8 . C9 . C4 . 120.849 yes
C11 . C10 . O2 . 121.759 yes
C11 . C10 . N3 . 115.011 yes
O2 . C10 . N3 . 123.229 yes
H113 . C11 . H112 . 110.327 no
H113 . C11 . H111 . 107.477 no
H112 . C11 . H111 . 108.709 no
H113 . C11 . C10 . 110.093 no
H112 . C11 . C10 . 110.763 no
H111 . C11 . C10 . 109.396 no
H131 . O13 . C12 . 122.749 no
H123 . C12 . H122 . 111.394 no
H123 . C12 . H121 . 104.433 no
H122 . C12 . H121 . 108.549 no
H123 . C12 . O13 . 109.552 no
H122 . C12 . O13 . 114.646 no
H121 . C12 . O13 . 107.692 no