A new polymorph of metacetamol
McGregor, Lindsay; Rychkov, Denis A.; Coster, Paul L.; Day, Sarah; Drebushchak, Valeri A.; Achkasov, Andrei F.; Nichol, Gary S.; Pulham, Colin R.; Boldyreva, Elena V.; CrystEngComm 17 (2015) 6183–; doi:10.1039/C5CE00910C

data_7221546
_publ_section_title
;
 A new polymorph of metacetamol
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              6183
_journal_paper_doi               10.1039/C5CE00910C
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          400
_chemical_name_common            'Metacetamol, 3-Acetamidophenol'
_chemical_name_systematic        N-(3-Hydroxyphenyl)acetamide
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-21 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.388(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.6202(8)
_cell_length_b                   19.010(3)
_cell_length_c                   10.1116(8)
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9920
_cell_measurement_theta_min      4.6170
_cell_volume                     1464.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -50.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686   38.0000 -180.0000 82

  2 omega -119.00   -4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686  -19.0000 -150.0000 115

  3 omega  -50.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686   38.0000   30.0000 82

  4 omega   55.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686 -178.0000 -120.0000 71

  5 omega   57.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686  178.0000    0.0000 70

  6 omega   57.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686  178.0000  150.0000 70

  7 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 82

  8 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000    0.0000 91

  9 omega   66.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000    0.0000 112

 10 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   90.0000 84

 11 omega   83.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 95

 12 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 79

 13 omega   66.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 112

 14 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 55

 15 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -60.0000 105

 16 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000    0.0000 105

 17 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -150.0000 82

 18 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -30.0000 82

 19 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 58

 20 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -120.0000 79

 21 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -150.0000 79

 22 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 55

 23 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 79

 24 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 79

 25 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   30.0000 84

 26 omega   80.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   93.0488 98

 27 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   90.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0240335000
_diffrn_orient_matrix_UB_12      0.0758259000
_diffrn_orient_matrix_UB_13      -0.0506676000
_diffrn_orient_matrix_UB_21      -0.1816562000
_diffrn_orient_matrix_UB_22      -0.0197432000
_diffrn_orient_matrix_UB_23      -0.0565049000
_diffrn_orient_matrix_UB_31      -0.0851558000
_diffrn_orient_matrix_UB_32      0.0206473000
_diffrn_orient_matrix_UB_33      0.1322203000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16385
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         4.372
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014) was used for absorption correction. wR2(int) was 0.1584 before and 0.1141 after correction. The Ratio of minimum to maximum transmission is 0.7067. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.6518
_exptl_crystal_size_mid          0.4979
_exptl_crystal_size_min          0.0477
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     305
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.1094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1607P)^2^+9.3877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3354
_refine_ls_wR_factor_ref         0.3476
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4228
_reflns_number_total             5281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce00910c2.cif
_cod_data_source_block           cp4013
_cod_depositor_comments          'Adding full bibliography for 7221546.cif.'
_cod_original_cell_volume        1464.8(3)
_cod_database_code               7221546
_chemical_oxdiff_formula         'C8 H9 N O2'
_chemical_oxdiff_usercomment     '@ 120 K metacetemol'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1 = O11-H11 = O31-H31 = O21-H21
 0.84 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C2(H2), C4(H4), C5(H5), C6(H6), N21(H21A), C22(H22), C24(H24),
 C25(H25), C26(H26), N31(H31A), C32(H32), C34(H34), C35(H35), C36(H36),
 N11(H11A), C12(H12), C14(H14), C15(H15), C16(H16)
4.b Tetrahedral OH refined with riding coordinates:
 O31(H31)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C28(H28A,H28B,H28C), C38(H38A,H38B,H38C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              58437
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 11/7/14
_olex2_date_sample_submission    11/7/14
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id Metacetamol
_olex2_submission_special_instructions 'No special instructions were received'