# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cp4013
_database_code_depnum_ccdc_archive 'CCDC 1063964'
_audit_update_record             
;
2015-06-21 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;
_audit_creation_date             2015-06-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            'Metacetamol, 3-Acetamidophenol'
_chemical_name_systematic        N-(3-Hydroxyphenyl)acetamide
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_absolute_configuration ad
_chemical_melting_point          400
_chemical_oxdiff_formula         'C8 H9 N O2'
_chemical_oxdiff_usercomment     '@ 120 K metacetemol'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6202(8)
_cell_length_b                   19.010(3)
_cell_length_c                   10.1116(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.388(8)
_cell_angle_gamma                90
_cell_volume                     1464.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.9920
_cell_measurement_theta_min      4.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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 λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686   38.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega -119.00   -4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686  -19.0000 -150.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6686   38.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega   55.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686 -178.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686  178.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6686  178.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  8 omega   87.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 10 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   61.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 13 omega   66.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 112

#__ type_ start__ end____ width___ exp.time_
 14 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
 16 omega   37.00  142.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -125.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   98.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 20 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 21 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
 22 omega   36.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -30.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
 24 omega   30.00  109.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -94.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 25 omega   94.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  125.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
 26 omega   80.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   93.0488 98

#__ type_ start__ end____ width___ exp.time_
 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       'ω 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_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_number         0
_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_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.1094
_refine_ls_restrained_S_all      1.032
_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/[σ²(Fo²)+(0.1607P)²+9.3877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3354
_refine_ls_wR_factor_ref         0.3476



_refine_special_details          
;
As is clear from an examination of the displacement ellipsoids, this was a difficult sample.  The crystals were of rather poor quality with consistently poor shape (ragged edges, obvious stacking problems) and gave a poor quality, very streaky diffraction pattern.  Ordinarily they would have been rejected for data collection.  However, repeated recrystallizations had failed to yield anything better and so a data set was collected.  Several features of the CrysAlisPro software were used to try to get the best out of this poor diffraction pattern and the best result was achieved using the "follow sudden discontinuous orientation changes" option.  This is designed to help in circumstances when the crystal moves during data collection.  However, it also is of great help in optimizing the shoeboxes used in integration in cases such as this where the diffraction spots are very broad.

The unit cell parameters index as monoclinic with a beta angle of 90.4 degrees.  This is consistent with X-ray powder diffraction data.   Three orthorhombic forms of this compond have been reported (MENSEE, MENSEE01, MENSEE02) with similar unit cell parameters and space group Pna21.  In CP4013 the systematic absences indicate quite clearly (despite poor data quality) that Pna21 is not possible.  Only systematic absences corresponding to the 21 screw axis in space group P21 are observed and indeed the structure solved easily with direct methods in this space group.  The structure could not be solved in space group Pna21.    No overlooked additional symmetry in space group P21 is noted.

The quality of the intensity data is quite obvious when an displacement ellipsoid plot is inspected: all ellipsoids are oriented in the same direction and all are quite significantly prolate.  A strong similarity restraint (RIGU in SHELXL) was used to prevent several atoms from becoming non-positive definite during anisotropic refinement.   C-bound H atoms were placed in calculated positions.  O-bound H atoms were placed according to likely hydrogen bonding interactions and refined with restrained O-H distances.    The  value of the absolute structure parameter could not be established reliably but Friedel pairs were not merged during refinement.


#===============================================================================
The Following Improvement and Query ALERTS were generated - (Acta-Mode) <<<
#===============================================================================
     Format: alert-number_ALERT_alert-type_alert-level text
 
213_ALERT_2_A Atom C11             has ADP max/min Ratio .....        5.4 prolat
213_ALERT_2_A Atom C16             has ADP max/min Ratio .....        5.5 prolat

See above for an explanation of the problems with this structure.

#===============================================================================
250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.3 Note
250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....        7.3 Note
250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor ....        5.0 Note
340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0174 Ang.

See above for an explanation of the problems with this structure.

#===============================================================================
082_ALERT_2_C High R1 Value ..................................       0.11 Report
084_ALERT_3_C High wR2 Value (i.e. > 0.25) ...................       0.34 Report
089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.72 Note

See above for an explanation of the problems with this structure.

097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.67 eA-3
098_ALERT_2_C Large Reported Min.  (Negative) Residual Density      -0.70 eA-3
213_ALERT_2_C Atom N11             has ADP max/min Ratio .....        3.5 prolat
213_ALERT_2_C Atom C12             has ADP max/min Ratio .....        3.5 prolat
213_ALERT_2_C Atom C21             has ADP max/min Ratio .....        3.6 prolat
213_ALERT_2_C Atom C23             has ADP max/min Ratio .....        3.7 prolat
250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.9 Note
420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...     Please Check
420_ALERT_2_C D-H Without Acceptor       N11    -   H11A   ...     Please Check
420_ALERT_2_C D-H Without Acceptor       N21    -   H21A   ...     Please Check
420_ALERT_2_C D-H Without Acceptor       N31    -   H31A   ...     Please Check
906_ALERT_3_C Large K value in the Analysis of Variance ......      2.595 Check
911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          9 Report
#===============================================================================


;


# start Validation Reply Form
_vrf_PLAT213_cp4013              
;
PROBLEM: Atom C11             has ADP max/min Ratio .....        5.4 prolat
RESPONSE: For a discussion of problems encountered, please see 
_refine_special_details
;
# end Validation Reply Form




_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8440(12) 0.1669(5) 1.0179(7) 0.0321(17) Uani 1 1 d D U . . .
H1 H 0.800(19) 0.185(7) 1.086(9) 0.039 Uiso 1 1 d DR . . . .
O2 O 0.9936(11) 0.4178(5) 1.0227(7) 0.0319(17) Uani 1 1 d . U . . .
N1 N 0.9605(13) 0.3898(6) 0.8053(9) 0.0289(18) Uani 1 1 d . U . . .
H1A H 0.9493 0.4081 0.7257 0.035 Uiso 1 1 calc R . . . .
C1 C 0.9666(15) 0.3171(7) 0.8098(10) 0.0248(18) Uani 1 1 d . U . . .
C2 C 0.9049(15) 0.2787(7) 0.9172(10) 0.0245(18) Uani 1 1 d . U . . .
H2 H 0.8607 0.3027 0.9924 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9073(15) 0.2074(7) 0.9152(10) 0.0248(19) Uani 1 1 d . U . . .
C4 C 0.9747(15) 0.1698(7) 0.8081(10) 0.029(2) Uani 1 1 d . U . . .
H4 H 0.9783 0.1198 0.8080 0.035 Uiso 1 1 calc R . . . .
C5 C 1.0365(15) 0.2089(7) 0.7011(11) 0.027(2) Uani 1 1 d . U . . .
H5 H 1.0825 0.1849 0.6266 0.033 Uiso 1 1 calc R . . . .
C6 C 1.0326(14) 0.2809(7) 0.7009(10) 0.0260(19) Uani 1 1 d . U . . .
H6 H 1.0748 0.3062 0.6266 0.031 Uiso 1 1 calc R . . . .
C7 C 0.9693(13) 0.4375(7) 0.9067(10) 0.0258(18) Uani 1 1 d . U . . .
C8 C 0.9468(16) 0.5122(7) 0.8733(12) 0.032(2) Uani 1 1 d . U . . .
H8A H 0.8312 0.5282 0.9027 0.048 Uiso 1 1 calc GR . . . .
H8B H 0.9559 0.5183 0.7773 0.048 Uiso 1 1 calc GR . . . .
H8C H 1.0384 0.5399 0.9175 0.048 Uiso 1 1 calc GR . . . .
O21 O 0.8684(12) 0.5037(5) 0.2115(8) 0.0334(18) Uani 1 1 d D U . . .
H21 H 0.917(19) 0.481(7) 0.151(11) 0.040 Uiso 1 1 d DR . . . .
O22 O 0.7418(13) 0.2522(5) 0.2141(7) 0.036(2) Uani 1 1 d . U . . .
N21 N 0.7700(12) 0.2811(6) 0.4301(9) 0.0265(17) Uani 1 1 d . U . . .
H21A H 0.7796 0.2630 0.5099 0.032 Uiso 1 1 calc R . . . .
C21 C 0.7604(14) 0.3537(6) 0.4254(10) 0.0228(17) Uani 1 1 d . U . . .
C22 C 0.8162(14) 0.3928(7) 0.3145(10) 0.0244(18) Uani 1 1 d . U . . .
H22 H 0.8578 0.3691 0.2381 0.029 Uiso 1 1 calc R . . . .
C23 C 0.8106(14) 0.4641(6) 0.3168(10) 0.0241(18) Uani 1 1 d . U . . .
C24 C 0.7485(16) 0.5015(7) 0.4268(11) 0.031(2) Uani 1 1 d . U . . .
H24 H 0.7427 0.5515 0.4270 0.038 Uiso 1 1 calc R . . . .
C25 C 0.6956(18) 0.4620(7) 0.5360(12) 0.032(2) Uani 1 1 d . U . . .
H25 H 0.6553 0.4860 0.6125 0.039 Uiso 1 1 calc R . . . .
C26 C 0.6999(16) 0.3910(7) 0.5366(11) 0.029(2) Uani 1 1 d . U . . .
H26 H 0.6617 0.3660 0.6126 0.035 Uiso 1 1 calc R . . . .
C27 C 0.7668(15) 0.2334(7) 0.3296(10) 0.0279(19) Uani 1 1 d . U . . .
C28 C 0.7976(18) 0.1595(7) 0.3652(12) 0.036(2) Uani 1 1 d . U . . .
H28A H 0.7131 0.1296 0.3182 0.054 Uiso 1 1 calc GR . . . .
H28B H 0.7832 0.1535 0.4608 0.054 Uiso 1 1 calc GR . . . .
H28C H 0.9171 0.1461 0.3403 0.054 Uiso 1 1 calc GR . . . .
O31 O 0.3203(11) 0.4972(5) 0.7117(7) 0.0321(18) Uani 1 1 d D U . . .
H31 H 0.2795 0.4699 0.6538 0.038 Uiso 1 1 calc DR . . . .
O32 O 0.5070(12) 0.2511(5) 0.7055(7) 0.0338(18) Uani 1 1 d . U . . .
N31 N 0.4701(13) 0.2766(6) 0.9231(9) 0.0292(18) Uani 1 1 d . U . . .
H31A H 0.4647 0.2576 1.0023 0.035 Uiso 1 1 calc R . . . .
C31 C 0.4640(15) 0.3496(7) 0.9210(10) 0.026(2) Uani 1 1 d . U . . .
C32 C 0.3984(14) 0.3877(7) 0.8099(10) 0.0219(18) Uani 1 1 d . U . . .
H32 H 0.3617 0.3632 0.7326 0.026 Uiso 1 1 calc R . . . .
C33 C 0.3886(15) 0.4586(7) 0.8144(10) 0.025(2) Uani 1 1 d . U . . .
C34 C 0.4368(15) 0.4968(7) 0.9267(10) 0.029(2) Uani 1 1 d . U . . .
H34 H 0.4257 0.5466 0.9295 0.035 Uiso 1 1 calc R . . . .
C35 C 0.5021(16) 0.4588(7) 1.0349(12) 0.030(2) Uani 1 1 d . U . . .
H35 H 0.5380 0.4835 1.1122 0.036 Uiso 1 1 calc R . . . .
C36 C 0.5156(16) 0.3869(7) 1.0320(11) 0.030(2) Uani 1 1 d . U . . .
H36 H 0.5608 0.3625 1.1068 0.036 Uiso 1 1 calc R . . . .
C37 C 0.4831(14) 0.2297(7) 0.8215(10) 0.0267(18) Uani 1 1 d . U . . .
C38 C 0.4734(17) 0.1540(7) 0.8519(12) 0.034(2) Uani 1 1 d . U . . .
H38A H 0.3626 0.1349 0.8177 0.051 Uiso 1 1 calc GR . . . .
H38B H 0.4791 0.1472 0.9480 0.051 Uiso 1 1 calc GR . . . .
H38C H 0.5719 0.1296 0.8104 0.051 Uiso 1 1 calc GR . . . .
O11 O 0.4169(12) 0.1648(5) 0.5081(8) 0.036(2) Uani 1 1 d D U . . .
H11 H 0.44(2) 0.186(7) 0.579(8) 0.043 Uiso 1 1 d DR . . . .
O12 O 0.2298(12) 0.4116(5) 0.5136(7) 0.0342(19) Uani 1 1 d . U . . .
N11 N 0.2508(12) 0.3840(6) 0.2954(8) 0.0257(17) Uani 1 1 d . U . . .
H11A H 0.2514 0.4024 0.2156 0.031 Uiso 1 1 calc R . . . .
C11 C 0.2585(13) 0.3112(7) 0.3009(9) 0.0217(17) Uani 1 1 d . U . . .
C12 C 0.3317(14) 0.2740(7) 0.4091(10) 0.0244(18) Uani 1 1 d . U . . .
H12 H 0.3713 0.2990 0.4850 0.029 Uiso 1 1 calc R . . . .
C13 C 0.3458(13) 0.2029(6) 0.4050(10) 0.0225(18) Uani 1 1 d . U . . .
C14 C 0.2956(17) 0.1646(8) 0.2927(11) 0.034(2) Uani 1 1 d . U . . .
H14 H 0.3110 0.1151 0.2882 0.041 Uiso 1 1 calc R . . . .
C15 C 0.2216(16) 0.2025(7) 0.1873(11) 0.030(2) Uani 1 1 d . U . . .
H15 H 0.1795 0.1773 0.1124 0.036 Uiso 1 1 calc R . . . .
C16 C 0.2077(13) 0.2728(7) 0.1877(10) 0.0235(17) Uani 1 1 d . U . . .
H16 H 0.1637 0.2966 0.1119 0.028 Uiso 1 1 calc R . . . .
C17 C 0.2424(16) 0.4313(8) 0.3985(10) 0.032(2) Uani 1 1 d . U . . .
C18 C 0.2510(18) 0.5065(8) 0.3652(12) 0.037(2) Uani 1 1 d . U . . .
H18A H 0.3612 0.5263 0.3991 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.1517 0.5311 0.4055 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.2458 0.5122 0.2690 0.056 Uiso 1 1 calc GR . . . .


_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
O1 H1 0.84(3) . ?
O1 C3 1.381(14) . ?
O2 C7 1.244(14) . ?
N1 H1A 0.8800 . ?
N1 C1 1.385(17) . ?
N1 C7 1.370(15) . ?
C1 C2 1.392(16) . ?
C1 C6 1.396(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.357(17) . ?
C3 C4 1.398(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.470(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O21 H21 0.84(3) . ?
O21 C23 1.379(14) . ?
O22 C27 1.236(14) . ?
N21 H21A 0.8800 . ?
N21 C21 1.382(16) . ?
N21 C27 1.361(15) . ?
C21 C22 1.414(15) . ?
C21 C26 1.410(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.357(17) . ?
C23 C24 1.405(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.396(18) . ?
C25 H25 0.9500 . ?
C25 C26 1.352(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.469(19) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O31 H31 0.8400 . ?
O31 C33 1.372(14) . ?
O32 C37 1.256(14) . ?
N31 H31A 0.8800 . ?
N31 C31 1.389(17) . ?
N31 C37 1.364(15) . ?
C31 C32 1.425(15) . ?
C31 C36 1.382(16) . ?
C32 H32 0.9500 . ?
C32 C33 1.351(17) . ?
C33 C34 1.395(16) . ?
C34 H34 0.9500 . ?
C34 C35 1.400(17) . ?
C35 H35 0.9500 . ?
C35 C36 1.372(19) . ?
C36 H36 0.9500 . ?
C37 C38 1.474(19) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O11 H11 0.84(3) . ?
O11 C13 1.378(14) . ?
O12 C17 1.227(14) . ?
N11 H11A 0.8800 . ?
N11 C11 1.387(16) . ?
N11 C17 1.379(16) . ?
C11 C12 1.414(15) . ?
C11 C16 1.409(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.357(17) . ?
C13 C14 1.400(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.402(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.340(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.47(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C3 O1 H1 122(10) . . ?
C1 N1 H1A 115.3 . . ?
C7 N1 H1A 115.3 . . ?
C7 N1 C1 129.4(10) . . ?
N1 C1 C2 122.5(10) . . ?
N1 C1 C6 118.6(10) . . ?
C2 C1 C6 118.9(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(11) . . ?
C3 C2 H2 119.8 . . ?
O1 C3 C4 115.5(11) . . ?
C2 C3 O1 122.7(10) . . ?
C2 C3 C4 121.8(11) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.1(12) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(11) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.9(11) . . ?
C5 C6 H6 120.0 . . ?
O2 C7 N1 120.9(12) . . ?
O2 C7 C8 121.6(10) . . ?
N1 C7 C8 117.5(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C23 O21 H21 115(10) . . ?
C21 N21 H21A 115.2 . . ?
C27 N21 H21A 115.2 . . ?
C27 N21 C21 129.7(10) . . ?
N21 C21 C22 122.4(10) . . ?
N21 C21 C26 119.5(10) . . ?
C26 C21 C22 118.0(11) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(11) . . ?
C23 C22 H22 119.9 . . ?
O21 C23 C24 116.5(11) . . ?
C22 C23 O21 121.4(10) . . ?
C22 C23 C24 122.1(11) . . ?
C23 C24 H24 121.5 . . ?
C25 C24 C23 117.0(12) . . ?
C25 C24 H24 121.5 . . ?
C24 C25 H25 118.9 . . ?
C26 C25 C24 122.3(12) . . ?
C26 C25 H25 118.9 . . ?
C21 C26 H26 119.8 . . ?
C25 C26 C21 120.5(11) . . ?
C25 C26 H26 119.8 . . ?
O22 C27 N21 121.0(12) . . ?
O22 C27 C28 122.1(11) . . ?
N21 C27 C28 116.9(10) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C33 O31 H31 109.5 . . ?
C31 N31 H31A 114.9 . . ?
C37 N31 H31A 114.9 . . ?
C37 N31 C31 130.1(10) . . ?
N31 C31 C32 122.1(10) . . ?
C36 C31 N31 119.4(10) . . ?
C36 C31 C32 118.5(12) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(10) . . ?
C33 C32 H32 120.0 . . ?
O31 C33 C34 115.7(11) . . ?
C32 C33 O31 122.0(10) . . ?
C32 C33 C34 122.2(11) . . ?
C33 C34 H34 121.4 . . ?
C33 C34 C35 117.2(12) . . ?
C35 C34 H34 121.4 . . ?
C34 C35 H35 119.2 . . ?
C36 C35 C34 121.6(12) . . ?
C36 C35 H35 119.2 . . ?
C31 C36 H36 119.8 . . ?
C35 C36 C31 120.5(11) . . ?
C35 C36 H36 119.8 . . ?
O32 C37 N31 120.2(11) . . ?
O32 C37 C38 121.3(11) . . ?
N31 C37 C38 118.5(10) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C13 O11 H11 118(10) . . ?
C11 N11 H11A 115.7 . . ?
C17 N11 H11A 115.7 . . ?
C17 N11 C11 128.6(9) . . ?
N11 C11 C12 123.0(10) . . ?
N11 C11 C16 118.3(9) . . ?
C16 C11 C12 118.3(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(11) . . ?
C13 C12 H12 119.9 . . ?
O11 C13 C14 116.3(11) . . ?
C12 C13 O11 122.1(10) . . ?
C12 C13 C14 121.5(11) . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 117.1(13) . . ?
C15 C14 H14 121.5 . . ?
C14 C15 H15 118.6 . . ?
C16 C15 C14 122.8(11) . . ?
C16 C15 H15 118.6 . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.8(11) . . ?
C15 C16 H16 120.1 . . ?
O12 C17 N11 121.5(13) . . ?
O12 C17 C18 121.2(11) . . ?
N11 C17 C18 117.3(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 H1 O22 0.84(3) 1.87(6) 2.682(12) 160(15) 1_556
O21 H21 O2 0.84(3) 1.86(4) 2.691(12) 169(15) 1_554
O31 H31 O12 0.84 1.84 2.668(12) 169.6 .
O11 H11 O32 0.84(3) 1.85(5) 2.670(11) 165(15) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 178.7(10) . . . . ?
N1 C1 C2 C3 177.4(10) . . . . ?
N1 C1 C6 C5 -178.5(10) . . . . ?
C1 N1 C7 O2 3.5(18) . . . . ?
C1 N1 C7 C8 -175.8(10) . . . . ?
C1 C2 C3 O1 -178.5(10) . . . . ?
C1 C2 C3 C4 1.5(18) . . . . ?
C2 C1 C6 C5 -0.3(16) . . . . ?
C2 C3 C4 C5 -1.3(17) . . . . ?
C3 C4 C5 C6 0.3(17) . . . . ?
C4 C5 C6 C1 0.4(17) . . . . ?
C6 C1 C2 C3 -0.6(16) . . . . ?
C7 N1 C1 C2 30.2(17) . . . . ?
C7 N1 C1 C6 -151.7(11) . . . . ?
O21 C23 C24 C25 -177.7(11) . . . . ?
N21 C21 C22 C23 -177.4(10) . . . . ?
N21 C21 C26 C25 177.5(11) . . . . ?
C21 N21 C27 O22 -5.0(19) . . . . ?
C21 N21 C27 C28 173.9(11) . . . . ?
C21 C22 C23 O21 178.3(9) . . . . ?
C21 C22 C23 C24 -0.7(17) . . . . ?
C22 C21 C26 C25 0.1(17) . . . . ?
C22 C23 C24 C25 1.3(17) . . . . ?
C23 C24 C25 C26 -1.3(19) . . . . ?
C24 C25 C26 C21 1(2) . . . . ?
C26 C21 C22 C23 0.0(15) . . . . ?
C27 N21 C21 C22 -26.8(17) . . . . ?
C27 N21 C21 C26 155.9(12) . . . . ?
O31 C33 C34 C35 178.2(11) . . . . ?
N31 C31 C32 C33 177.4(11) . . . . ?
N31 C31 C36 C35 -176.6(11) . . . . ?
C31 N31 C37 O32 6.2(18) . . . . ?
C31 N31 C37 C38 -175.4(11) . . . . ?
C31 C32 C33 O31 -177.5(10) . . . . ?
C31 C32 C33 C34 -1.6(18) . . . . ?
C32 C31 C36 C35 0.6(18) . . . . ?
C32 C33 C34 C35 2.0(18) . . . . ?
C33 C34 C35 C36 -1.1(19) . . . . ?
C34 C35 C36 C31 0(2) . . . . ?
C36 C31 C32 C33 0.3(17) . . . . ?
C37 N31 C31 C32 27.0(18) . . . . ?
C37 N31 C31 C36 -155.9(12) . . . . ?
O11 C13 C14 C15 179.5(10) . . . . ?
N11 C11 C12 C13 -175.7(10) . . . . ?
N11 C11 C16 C15 176.7(10) . . . . ?
C11 N11 C17 O12 -4.6(18) . . . . ?
C11 N11 C17 C18 174.8(10) . . . . ?
C11 C12 C13 O11 179.8(9) . . . . ?
C11 C12 C13 C14 2.7(17) . . . . ?
C12 C11 C16 C15 3.2(15) . . . . ?
C12 C13 C14 C15 -3.3(18) . . . . ?
C13 C14 C15 C16 4.0(19) . . . . ?
C14 C15 C16 C11 -4.1(18) . . . . ?
C16 C11 C12 C13 -2.5(15) . . . . ?
C17 N11 C11 C12 -27.8(16) . . . . ?
C17 N11 C11 C16 158.9(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5 0 0 0.2322 -4.9402 -0.2045 -0.3307 0.1200 0.9201 0.3727
5 0 0 0.2419 4.9473 -0.0990 -0.2220 -0.1152 -0.8842 -0.4527
0 1 0 0.0239 0.0033 0.9995 -0.0011 0.0758 -0.0203 0.0202
0 -3 -6 0.2639 -0.0621 -3.4568 -6.2951 0.0583 0.4352 -0.8984
0 2 5 0.3519 0.0016 1.9851 5.0045 -0.1031 -0.3223 0.7025
-1 3 5 0.3172 -0.9943 2.9926 5.0024 -0.0026 -0.1611 0.8079
1 1 5 0.3700 0.9975 0.9777 5.0065 -0.2035 -0.4834 0.5972
0 -1 0 0.0239 -0.0033 -0.9995 0.0011 -0.0758 0.0203 -0.0202

_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'
# start Validation Reply Form
_chemical_properties_physical    Moisture-sensitive
