#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/14/2201497.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201497
loop_
_publ_author_name
'Oswald, Iain D. H.'
'Motherwell, W. D. Sam'
'Parsons, Simon'
'Pulham, Colin R.'
_publ_section_title
;
 A paracetamol--morpholine adduct
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1290
_journal_page_last               o1292
_journal_paper_doi               10.1107/S1600536802018111
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C8 H9 N O2, 2.5C4 H9 N O'
_chemical_formula_moiety         'C8 H9 N O2, 2.5C4 H9 N O'
_chemical_formula_sum            'C18 H31.5 N3.5 O4.5'
_chemical_formula_weight         368.97
_chemical_name_common            'paracetamol--morpholine (1/2.5)'
_chemical_name_systematic
;
N-(4-hydroxyphenyl)acetamide--morpholine (1/2.5)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   calc/difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.35(3)
_cell_angle_beta                 108.33(2)
_cell_angle_gamma                96.68(3)
_cell_formula_units_Z            2
_cell_length_a                   8.710(4)
_cell_length_b                   9.920(5)
_cell_length_c                   12.385(5)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      20
_cell_volume                     972.7(8)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1990)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1990)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and CAMERON (Watkin et al., 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3596
_diffrn_reflns_theta_full        70.30
_diffrn_reflns_theta_max         70.30
_diffrn_reflns_theta_min         3.90
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
via ψ scans [SHELXTL (Sheldrick (2001) based on
method of North et al. (1968)]
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.264
_refine_ls_extinction_coef       0.0077(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0983P)²+0.3346P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1782
_reflns_number_gt                1951
_reflns_number_total             3416
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6004.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        972.7(7)
_cod_original_formula_sum        'C18 H31.50 N3.50 O4.50'
_cod_database_code               2201497
_cod_database_fobs_code          2201497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.3543(3) 0.9687(3) 0.32398(19) 0.0407(6) Uani d . 1 . . O
H11 0.268(6) 0.901(5) 0.249(4) 0.081(14) Uiso d . 1 . . H
C1 0.4893(4) 1.0247(3) 0.3041(2) 0.0325(7) Uani d . 1 . . C
C2 0.6318(4) 1.0856(3) 0.4007(2) 0.0340(7) Uani d . 1 . . C
H2 0.6327 1.0862 0.4761 0.041 Uiso calc R 1 . . H
C3 0.7720(4) 1.1452(3) 0.3858(2) 0.0320(7) Uani d . 1 . . C
H3 0.8668 1.1852 0.4515 0.038 Uiso calc R 1 . . H
C4 0.7745(3) 1.1470(3) 0.2738(2) 0.0298(7) Uani d . 1 . . C
C5 0.6316(4) 1.0851(3) 0.1770(2) 0.0337(7) Uani d . 1 . . C
H5 0.6303 1.0852 0.1017 0.040 Uiso calc R 1 . . H
C6 0.4907(4) 1.0231(3) 0.1915(3) 0.0360(7) Uani d . 1 . . C
H6 0.3967 0.9802 0.1258 0.043 Uiso calc R 1 . . H
N1 0.9251(3) 1.2109(3) 0.2681(2) 0.0339(6) Uani d . 1 . . N
H1 1.010(4) 1.254(4) 0.345(3) 0.047(10) Uiso d . 1 . . H
C7 0.9630(4) 1.2134(3) 0.1705(3) 0.0331(7) Uani d . 1 . . C
O2 0.8622(3) 1.1677(3) 0.06987(17) 0.0441(6) Uani d . 1 . . O
C8 1.1411(4) 1.2719(4) 0.1936(3) 0.0406(8) Uani d . 1 . . C
H8A 1.1982 1.1958 0.1826 0.061 Uiso calc R 1 . . H
H8B 1.1912 1.3301 0.2731 0.061 Uiso calc R 1 . . H
H8C 1.1475 1.3272 0.1397 0.061 Uiso calc R 1 . . H
N1A 1.1842(3) 1.3434(3) 0.5029(2) 0.0360(6) Uani d D 1 . . N
H1A1 1.130(4) 1.349(4) 0.554(3) 0.067(13) Uiso d D 1 . . H
C2A 1.2627(4) 1.4925(4) 0.5329(3) 0.0432(8) Uani d . 1 . . C
H2A1 1.1792 1.5496 0.5312 0.052 Uiso calc R 1 . . H
H2A2 1.3087 1.5067 0.4734 0.052 Uiso calc R 1 . . H
C3A 1.3979(4) 1.5420(4) 0.6527(3) 0.0468(9) Uani d . 1 . . C
H3A2 1.4504 1.6386 0.6652 0.056 Uiso calc R 1 . . H
H3A1 1.3505 1.5393 0.7135 0.056 Uiso calc R 1 . . H
O4A 1.5182(3) 1.4553(3) 0.6615(2) 0.0513(7) Uani d . 1 . . O
C5A 1.4447(4) 1.3107(4) 0.6411(3) 0.0492(9) Uani d . 1 . . C
H5A1 1.3981 1.3019 0.7014 0.059 Uiso calc R 1 . . H
H5A2 1.5288 1.2538 0.6463 0.059 Uiso calc R 1 . . H
C6A 1.3114(4) 1.2577(4) 0.5214(3) 0.0460(8) Uani d . 1 . . C
H6A2 1.3612 1.2564 0.4614 0.055 Uiso calc R 1 . . H
H6A1 1.2598 1.1618 0.5118 0.055 Uiso calc R 1 . . H
N1B 0.8948(3) 1.2115(3) -0.1501(2) 0.0369(6) Uani d D 1 . . N
H1B1 0.892(5) 1.210(4) -0.0788(17) 0.059(11) Uiso d D 1 . . H
C2B 1.0423(4) 1.1576(4) -0.1578(3) 0.0417(8) Uani d . 1 . . C
H2B1 1.0345 1.0628 -0.1485 0.050 Uiso calc R 1 . . H
H2B2 1.1401 1.2167 -0.0956 0.050 Uiso calc R 1 . . H
C3B 1.0541(4) 1.1578(4) -0.2767(3) 0.0419(8) Uani d . 1 . . C
H3B2 1.1515 1.1230 -0.2827 0.050 Uiso calc R 1 . . H
H3B1 0.9584 1.0951 -0.3383 0.050 Uiso calc R 1 . . H
O4B 1.0631(3) 1.2961(2) -0.29388(19) 0.0390(6) Uani d . 1 . . O
C5B 0.9246(4) 1.3526(4) -0.2823(3) 0.0402(8) Uani d . 1 . . C
H5B1 0.8251 1.2963 -0.3446 0.048 Uiso calc R 1 . . H
H5B2 0.9361 1.4476 -0.2912 0.048 Uiso calc R 1 . . H
C6B 0.9085(4) 1.3549(4) -0.1638(3) 0.0408(8) Uani d . 1 . . C
H6B2 1.0043 1.4159 -0.1011 0.049 Uiso calc R 1 . . H
H6B1 0.8113 1.3911 -0.1592 0.049 Uiso calc R 1 . . H
N1C 1.3689(3) 1.4607(3) 0.0409(2) 0.0497(7) Uani d PD 0.50 . 1 N
H1C1 1.430(9) 1.511(8) 0.115(3) 0.074 Uiso d PD 0.50 A 1 H
O1C 1.3689(3) 1.4607(3) 0.0409(2) 0.0497(7) Uani d P 0.50 . 2 O
C2C 1.4703(5) 1.3634(5) 0.0125(4) 0.0533(10) Uani d . 1 . . C
H2C2 1.429(6) 1.311(5) -0.082(4) 0.083(14) Uiso d . 1 . . H
H2C1 1.479(5) 1.299(4) 0.062(4) 0.065(12) Uiso d . 1 . . H
C3C 1.6388(5) 1.4367(5) 0.0272(4) 0.0526(10) Uani d . 1 . . C
H3CA 1.699(5) 1.486(4) 0.124(4) 0.068(12) Uiso d . 1 . . H
H3CB 1.705(5) 1.357(4) -0.004(3) 0.057(11) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 H11 . . 112(3)
O1 C1 C2 . . 117.9(2)
O1 C1 C6 . . 123.0(3)
C2 C1 C6 . . 119.1(3)
C3 C2 C1 . . 120.4(3)
C3 C2 H2 . . 119.8
C1 C2 H2 . . 119.8
C2 C3 C4 . . 121.3(3)
C2 C3 H3 . . 119.3
C4 C3 H3 . . 119.3
C5 C4 C3 . . 118.1(3)
C5 C4 N1 . . 125.1(3)
C3 C4 N1 . . 116.8(3)
C6 C5 C4 . . 120.8(3)
C6 C5 H5 . . 119.6
C4 C5 H5 . . 119.6
C5 C6 C1 . . 120.4(3)
C5 C6 H6 . . 119.8
C1 C6 H6 . . 119.8
C7 N1 C4 . . 127.8(3)
C7 N1 H1 . . 118(2)
C4 N1 H1 . . 114(2)
O2 C7 N1 . . 123.2(3)
O2 C7 C8 . . 121.7(3)
N1 C7 C8 . . 115.1(3)
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C6A N1A C2A . . 109.5(3)
C6A N1A H1A1 . . 115(3)
C2A N1A H1A1 . . 99(3)
N1A C2A C3A . . 113.2(3)
N1A C2A H2A1 . . 108.9
C3A C2A H2A1 . . 108.9
N1A C2A H2A2 . . 108.9
C3A C2A H2A2 . . 108.9
H2A1 C2A H2A2 . . 107.8
O4A C3A C2A . . 110.8(3)
O4A C3A H3A2 . . 109.5
C2A C3A H3A2 . . 109.5
O4A C3A H3A1 . . 109.5
C2A C3A H3A1 . . 109.5
H3A2 C3A H3A1 . . 108.1
C3A O4A C5A . . 111.2(3)
O4A C5A C6A . . 110.7(3)
O4A C5A H5A1 . . 109.5
C6A C5A H5A1 . . 109.5
O4A C5A H5A2 . . 109.5
C6A C5A H5A2 . . 109.5
H5A1 C5A H5A2 . . 108.1
N1A C6A C5A . . 113.3(3)
N1A C6A H6A2 . . 108.9
C5A C6A H6A2 . . 108.9
N1A C6A H6A1 . . 108.9
C5A C6A H6A1 . . 108.9
H6A2 C6A H6A1 . . 107.7
C6B N1B C2B . . 109.4(3)
C6B N1B H1B1 . . 111(3)
C2B N1B H1B1 . . 106(3)
N1B C2B C3B . . 108.6(3)
N1B C2B H2B1 . . 110.0
C3B C2B H2B1 . . 110.0
N1B C2B H2B2 . . 110.0
C3B C2B H2B2 . . 110.0
H2B1 C2B H2B2 . . 108.3
O4B C3B C2B . . 111.3(3)
O4B C3B H3B2 . . 109.4
C2B C3B H3B2 . . 109.4
O4B C3B H3B1 . . 109.4
C2B C3B H3B1 . . 109.4
H3B2 C3B H3B1 . . 108.0
C5B O4B C3B . . 111.1(2)
O4B C5B C6B . . 111.6(3)
O4B C5B H5B1 . . 109.3
C6B C5B H5B1 . . 109.3
O4B C5B H5B2 . . 109.3
C6B C5B H5B2 . . 109.3
H5B1 C5B H5B2 . . 108.0
N1B C6B C5B . . 108.9(3)
N1B C6B H6B2 . . 109.9
C5B C6B H6B2 . . 109.9
N1B C6B H6B1 . . 109.9
C5B C6B H6B1 . . 109.9
H6B2 C6B H6B1 . . 108.3
C2C N1C C3C . 2_885 110.3(3)
C2C N1C H1C1 . . 104(6)
C3C N1C H1C1 2_885 . 104(6)
N1C C2C C3C . . 112.5(4)
N1C C2C H2C2 . . 113(2)
C3C C2C H2C2 . . 98(2)
N1C C2C H2C1 . . 109(2)
C3C C2C H2C1 . . 110(2)
H2C2 C2C H2C1 . . 114(3)
O1C C3C N1C 2_885 2_885 0.0(2)
O1C C3C C2C 2_885 . 111.8(3)
N1C C3C C2C 2_885 . 111.8(3)
O1C C3C H3CA 2_885 . 113(2)
N1C C3C H3CA 2_885 . 113(2)
C2C C3C H3CA . . 105(2)
O1C C3C H3CB 2_885 . 108.3(19)
N1C C3C H3CB 2_885 . 108.3(19)
C2C C3C H3CB . . 108(2)
H3CA C3C H3CB . . 111(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.357(3) ?
O1 H11 . 1.02(5) ?
C1 C2 . 1.386(4) ?
C1 C6 . 1.394(4) ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.398(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.390(4) ?
C4 N1 . 1.418(4) ?
C5 C6 . 1.388(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
N1 C7 . 1.354(4) ?
N1 H1 . 0.97(4) ?
C7 O2 . 1.228(4) ?
C7 C8 . 1.505(4) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
N1A C6A . 1.465(4) ?
N1A C2A . 1.471(4) ?
N1A H1A1 . 0.892(10) ?
C2A C3A . 1.512(5) ?
C2A H2A1 . 0.9700 ?
C2A H2A2 . 0.9700 ?
C3A O4A . 1.424(4) ?
C3A H3A2 . 0.9700 ?
C3A H3A1 . 0.9700 ?
O4A C5A . 1.436(4) ?
C5A C6A . 1.505(5) ?
C5A H5A1 . 0.9700 ?
C5A H5A2 . 0.9700 ?
C6A H6A2 . 0.9700 ?
C6A H6A1 . 0.9700 ?
N1B C6B . 1.464(4) ?
N1B C2B . 1.470(4) ?
N1B H1B1 . 0.895(10) ?
C2B C3B . 1.509(4) ?
C2B H2B1 . 0.9700 ?
C2B H2B2 . 0.9700 ?
C3B O4B . 1.429(4) ?
C3B H3B2 . 0.9700 ?
C3B H3B1 . 0.9700 ?
O4B C5B . 1.421(4) ?
C5B C6B . 1.513(4) ?
C5B H5B1 . 0.9700 ?
C5B H5B2 . 0.9700 ?
C6B H6B2 . 0.9700 ?
C6B H6B1 . 0.9700 ?
N1C C2C . 1.444(5) ?
N1C C3C 2_885 1.450(4) ?
N1C H1C1 . 0.903(10) ?
C2C C3C . 1.497(5) ?
C2C H2C2 . 1.09(5) ?
C2C H2C1 . 0.97(4) ?
C3C O1C 2_885 1.450(4) ?
C3C N1C 2_885 1.450(4) ?
C3C H3CA . 1.12(4) ?
C3C H3CB . 1.11(4) ?
