Supplementary information for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Iain Oswald'
'C R Pulham'

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

_publ_section_title              
;
Co-crystallisation at high pressure - an additional
tool for the preparation and study of co-crystals
;

# Attachment 'CompoundI.cif'

data_CompoundI
_database_code_depnum_ccdc_archive 'CCDC 683518'
_audit_creation_date             08-02-26
_audit_creation_method           CRYSTALS_ver_12.85

_oxford_structure_analysis_title 'Parpip in P-1'
_chemical_name_systematic        '2:1:2 Paracetamol:piperazine:ethanol solvate'
_chemical_melting_point          ?

#looking for refcif

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

_cell_length_a                   7.544(5)
_cell_length_b                   8.604(7)
_cell_length_c                   10.394(3)
_cell_angle_alpha                93.18(5)
_cell_angle_beta                 97.73(4)
_cell_angle_gamma                114.70(5)
_cell_volume                     602.7(7)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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'
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 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'

_cell_formula_units_Z            2

# Given Formula = C12 H17 N3 O2
# Dc = 1.30 Fooo = 260.00 Mu = 0.90 M = 235.29
# Found Formula = C12 H20 N2 O3
# Dc = 1.32 FOOO = 260.00 Mu = 0.95 M = 240.30

_chemical_formula_sum            'C12 H20 N2 O3'
_chemical_formula_moiety         'C8 H9 N O2, 0.5(C4 H10 N2), C2 H6 O'
_chemical_compound_source        ?
_chemical_formula_weight         240.30

_cell_measurement_reflns_used    471
_cell_measurement_theta_min      3
_cell_measurement_theta_max      19
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.095

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device       'Bruker SMART APEX II'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'SMART (Siemens, 1993)'
_computing_cell_refinement       'SAINT (Siemens ,1995)'
_computing_data_reduction        'SAINT (Siemens ,1995)'
_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      293
_diffrn_ambient_pressure         570000
_diffrn_reflns_number            14105
_reflns_number_total             1043
_diffrn_reflns_av_R_equivalents  0.0934
# Number of reflections with Friedels Law is 1043
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1752

_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         23.354
_diffrn_measured_fraction_theta_max 0.591

_diffrn_reflns_theta_full        17.983
_diffrn_measured_fraction_theta_full 0.659

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -8
_reflns_limit_h_max              7
_reflns_limit_k_min              -6
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   3.31
_oxford_diffrn_Wilson_scale      0.12

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

_refine_diff_density_min         -0.27
_refine_diff_density_max         0.31

# 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>-10.0\s(I)
_refine_ls_number_reflns         1039
_refine_ls_number_restraints     130
_refine_ls_number_parameters     154
_oxford_refine_ls_R_factor_ref   0.1123
_refine_ls_wR_factor_ref         0.2084
_refine_ls_goodness_of_fit_ref   0.9272
_refine_ls_shift/su_max          0.000061

# The values computed from all data
_oxford_reflns_number_all        1039
_refine_ls_R_factor_all          0.1123
_refine_ls_wR_factor_all         0.2084

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                609
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_gt          0.1659

# 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    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.15P)^2^ + 0.00P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/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
O3 O 0.2890(6) 0.2677(6) 0.7748(4) 0.0703 1.0000 Uani . U . . . . .
C11 C 0.3258(9) 0.1206(11) 0.7340(7) 0.0638 1.0000 Uani . U . . . . .
C12 C 0.3179(8) 0.0062(10) 0.8324(6) 0.0630 1.0000 Uani . U . . . . .
H3 H 0.1931 0.2027 0.8091 0.1093 1.0000 Uiso R . . . . . .
H121 H 0.3430 -0.0864 0.8017 0.0850 1.0000 Uiso R . . . . . .
H122 H 0.4132 0.0713 0.9075 0.0850 1.0000 Uiso R . . . . . .
H123 H 0.1887 -0.0379 0.8562 0.0850 1.0000 Uiso R . . . . . .
H111 H 0.4539 0.1630 0.7108 0.0829 1.0000 Uiso R . . . . . .
H112 H 0.2291 0.0555 0.6596 0.0829 1.0000 Uiso R . . . . . .
O1 O 0.9388(4) 1.1401(5) 0.8670(3) 0.0521 1.0000 Uani . U . . . . .
C1 C 0.7941(6) 0.9890(10) 0.7973(5) 0.0439 1.0000 Uani . U . . . . .
C2 C 0.7398(7) 0.8414(9) 0.8500(5) 0.0451 1.0000 Uani . U . . . . .
C3 C 0.5915(6) 0.6873(9) 0.7827(5) 0.0440 1.0000 Uani . U . . . . .
C4 C 0.4926(7) 0.6891(9) 0.6592(5) 0.0407 1.0000 Uani . U . . . . .
C5 C 0.5477(7) 0.8388(9) 0.6053(5) 0.0431 1.0000 Uani . U . . . . .
C6 C 0.6983(7) 0.9915(9) 0.6729(5) 0.0477 1.0000 Uani . U . . . . .
C7 C 0.2282(7) 0.4892(10) 0.4779(5) 0.0502 1.0000 Uani . U . . . . .
C8 C 0.0752(7) 0.3028(8) 0.4460(6) 0.0535 1.0000 Uani . U . . . . .
O2 O 0.2539(5) 0.5873(7) 0.4001(4) 0.0614 1.0000 Uani . U . . . . .
N1 N 0.3390(5) 0.5257(7) 0.6000(4) 0.0467 1.0000 Uani . U . . . . .
H21 H 0.8043 0.8467 0.9406 0.0590 1.0000 Uiso R . . . . . .
H31 H 0.5615 0.5790 0.8224 0.0586 1.0000 Uiso R . . . . . .
H51 H 0.4884 0.8417 0.5191 0.0579 1.0000 Uiso R . . . . . .
H61 H 0.7389 1.0989 0.6337 0.0592 1.0000 Uiso R . . . . . .
H81 H 0.0787 0.2372 0.5185 0.0845 1.0000 Uiso R . . . . . .
H82 H 0.0982 0.2500 0.3701 0.0852 1.0000 Uiso R . . . . . .
H83 H -0.0556 0.2985 0.4247 0.0854 1.0000 Uiso R . . . . . .
H10 H 0.9114 1.2318 0.8828 0.0738 1.0000 Uiso R . . . . . .
H11 H 0.3263 0.4400 0.6464 0.0500 1.0000 Uiso R . . . . . .
N2 N 0.1242(5) 0.5894(6) 0.1211(4) 0.0538 1.0000 Uani . U . . . . .
C9 C 0.2081(7) 0.5674(9) 0.0039(5) 0.0571 1.0000 Uani . U . . . . .
C10 C -0.0690(7) 0.4394(9) 0.1175(5) 0.0541 1.0000 Uani . U . . . . .
H91 H 0.2242 0.4537 -0.0010 0.0710 1.0000 Uiso R . . . . . .
H92 H 0.3445 0.6554 0.0069 0.0703 1.0000 Uiso R . . . . . .
H101 H -0.0464 0.3330 0.1090 0.0700 1.0000 Uiso R . . . . . .
H102 H -0.1177 0.4451 0.1982 0.0695 1.0000 Uiso R . . . . . .
H2 H 0.1972 0.5627 0.1871 0.0634 1.0000 Uiso 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
O3 0.071(2) 0.044(3) 0.089(3) 0.007(3) 0.029(2) 0.015(2)
C11 0.062(4) 0.055(5) 0.072(4) 0.003(3) 0.023(3) 0.019(3)
C12 0.065(4) 0.047(5) 0.074(4) -0.001(3) 0.019(3) 0.021(3)
O1 0.0483(19) 0.037(3) 0.058(2) -0.013(3) -0.0030(16) 0.0119(19)
C1 0.029(2) 0.041(3) 0.052(3) -0.006(2) 0.0041(18) 0.008(2)
C2 0.041(3) 0.046(3) 0.046(3) -0.003(2) 0.002(2) 0.018(3)
C3 0.046(3) 0.039(4) 0.046(2) 0.002(3) 0.0044(19) 0.019(2)
C4 0.038(2) 0.038(3) 0.041(2) -0.002(2) 0.0067(18) 0.012(2)
C5 0.040(3) 0.044(3) 0.039(3) 0.002(2) 0.002(2) 0.015(3)
C6 0.046(3) 0.041(4) 0.047(2) 0.000(3) 0.0083(19) 0.011(2)
C7 0.043(3) 0.051(4) 0.043(2) -0.009(2) 0.010(2) 0.008(3)
C8 0.041(3) 0.051(4) 0.056(3) -0.011(3) 0.000(2) 0.012(3)
O2 0.068(2) 0.059(4) 0.045(2) -0.005(2) 0.002(2) 0.019(3)
N1 0.045(2) 0.037(3) 0.047(2) -0.004(2) 0.0051(16) 0.008(2)
N2 0.054(2) 0.047(4) 0.048(2) -0.011(3) -0.0036(18) 0.016(2)
C9 0.047(3) 0.056(5) 0.058(2) -0.007(4) 0.0012(19) 0.017(3)
C10 0.063(3) 0.045(5) 0.049(3) 0.002(4) 0.010(2) 0.019(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.03(13)
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
O3 . C11 . 1.458(11) yes
O3 . H3 . 0.847 no
C11 . C12 . 1.448(13) yes
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C12 . H121 . 0.942 no
C12 . H122 . 0.950 no
C12 . H123 . 0.960 no
O1 . C1 . 1.380(6) yes
O1 . H10 . 0.908 no
C1 . C2 . 1.336(10) yes
C1 . C6 . 1.400(9) yes
C2 . C3 . 1.395(7) yes
C2 . H21 . 0.989 no
C3 . C4 . 1.399(9) yes
C3 . H31 . 0.991 no
C4 . C5 . 1.358(10) yes
C4 . N1 . 1.431(7) yes
C5 . C6 . 1.395(7) yes
C5 . H51 . 0.953 no
C6 . H61 . 0.976 no
C7 . C8 . 1.518(9) yes
C7 . O2 . 1.177(9) yes
C7 . N1 . 1.364(7) yes
C8 . H81 . 0.970 no
C8 . H82 . 0.960 no
C8 . H83 . 0.967 no
N1 . H11 . 0.882 no
N2 . C9 . 1.484(5) yes
N2 . C10 . 1.483(6) yes
N2 . H2 . 0.921 no
C9 . C10 2_565 1.510(9) yes
C9 . H91 . 1.034 no
C9 . H92 . 0.986 no
C10 . H101 . 1.000 no
C10 . H102 . 0.967 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
C11 . O3 . H3 . 90.2 no
O3 . C11 . C12 . 114.8(6) yes
O3 . C11 . H111 . 108.2 no
C12 . C11 . H111 . 108.0 no
O3 . C11 . H112 . 108.2 no
C12 . C11 . H112 . 108.0 no
H111 . C11 . H112 . 109.5 no
C11 . C12 . H121 . 111.6 no
C11 . C12 . H122 . 108.3 no
H121 . C12 . H122 . 110.2 no
C11 . C12 . H123 . 108.7 no
H121 . C12 . H123 . 109.3 no
H122 . C12 . H123 . 108.7 no
C1 . O1 . H10 . 119.9 no
O1 . C1 . C2 . 120.3(6) yes
O1 . C1 . C6 . 119.9(7) yes
C2 . C1 . C6 . 119.8(5) yes
C1 . C2 . C3 . 121.4(6) yes
C1 . C2 . H21 . 117.3 no
C3 . C2 . H21 . 121.2 no
C2 . C3 . C4 . 119.1(7) yes
C2 . C3 . H31 . 119.2 no
C4 . C3 . H31 . 121.7 no
C3 . C4 . C5 . 119.5(5) yes
C3 . C4 . N1 . 114.8(7) yes
C5 . C4 . N1 . 125.6(5) yes
C4 . C5 . C6 . 120.7(6) yes
C4 . C5 . H51 . 121.0 no
C6 . C5 . H51 . 118.2 no
C1 . C6 . C5 . 119.3(7) yes
C1 . C6 . H61 . 120.0 no
C5 . C6 . H61 . 120.7 no
C8 . C7 . O2 . 122.0(5) yes
C8 . C7 . N1 . 113.4(7) yes
O2 . C7 . N1 . 124.4(5) yes
C7 . C8 . H81 . 111.8 no
C7 . C8 . H82 . 109.8 no
H81 . C8 . H82 . 109.3 no
C7 . C8 . H83 . 109.6 no
H81 . C8 . H83 . 109.3 no
H82 . C8 . H83 . 106.9 no
C4 . N1 . C7 . 126.9(6) yes
C4 . N1 . H11 . 114.1 no
C7 . N1 . H11 . 118.6 no
C9 . N2 . C10 . 109.4(4) yes
C9 . N2 . H2 . 103.4 no
C10 . N2 . H2 . 98.0 no
C10 2_565 C9 . N2 . 109.1(4) yes
C10 2_565 C9 . H91 . 108.2 no
N2 . C9 . H91 . 111.0 no
C10 2_565 C9 . H92 . 112.7 no
N2 . C9 . H92 . 112.9 no
H91 . C9 . H92 . 102.8 no
C9 2_565 C10 . N2 . 108.4(6) yes
C9 2_565 C10 . H101 . 107.7 no
N2 . C10 . H101 . 107.5 no
C9 2_565 C10 . H102 . 114.3 no
N2 . C10 . H102 . 110.2 no
H101 . C10 . H102 . 108.5 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
O3 . H3 . O1 1_445 153 0.85 1.95 2.735(9) yes
C2 . H21 . O1 2_777 161 0.99 2.55 3.502(9) yes
C3 . H31 . O3 . 136 0.99 2.57 3.358(9) yes
O1 . H10 . N2 2_676 167 0.91 1.67 2.563(9) yes
O1 . H10 . C9 2_676 160 0.91 2.56 3.424(9) yes
O1 . H10 . C10 2_676 140 0.91 2.57 3.317(9) yes
N1 . H11 . O3 . 171 0.88 2.01 2.881(9) yes
N2 . H2 . O2 . 139 0.92 2.18 2.937(9) yes


