# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ParacetmolFormII
_database_code_depnum_ccdc_archive 'CCDC 1814819'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;
_audit_creation_date             2018-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            Acetaminophen
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          441
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7678(7)
_cell_length_b                   7.1966(5)
_cell_length_c                   17.1615(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1453.38(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9099
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.37
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.567
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_temperature      100.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2198
_reflns_number_total             2436
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.082
_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)+(0.0597P)²+0.6192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1160
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
O2 O 0.89376(6) 0.22985(12) -0.00216(4) 0.02320(18) Uani 1 1 d . . . . .
O1 O 0.76089(6) 0.26295(11) 0.36909(4) 0.01779(16) Uani 1 1 d . . . . .
C2 C 0.77560(7) 0.20522(12) 0.23291(5) 0.01331(17) Uani 1 1 d . . . . .
H2 H 0.701992 0.151035 0.233655 0.016 Uiso 1 1 calc R . . . .
C4 C 0.94504(7) 0.29212(12) 0.16216(5) 0.01223(17) Uani 1 1 d . . . . .
N1 N 1.01748(6) 0.29363(11) 0.09607(4) 0.01464(16) Uani 1 1 d . . . . .
C1 C 0.82176(7) 0.27683(12) 0.30123(5) 0.01269(17) Uani 1 1 d . . . . .
C3 C 0.83670(7) 0.21246(12) 0.16328(5) 0.01327(17) Uani 1 1 d . . . . .
H3 H 0.804777 0.163401 0.116786 0.016 Uiso 1 1 calc R . . . .
C7 C 0.99142(8) 0.26329(13) 0.02060(5) 0.01505(18) Uani 1 1 d . . . . .
C8 C 1.09187(8) 0.27129(15) -0.03401(6) 0.01962(19) Uani 1 1 d . . . . .
H8A H 1.120433 0.145272 -0.043209 0.029 Uiso 1 1 calc GR . . . .
H8B H 1.152067 0.347124 -0.010646 0.029 Uiso 1 1 calc GR . . . .
H8C H 1.068317 0.326667 -0.083614 0.029 Uiso 1 1 calc GR . . . .
C5 C 0.98927(7) 0.36933(12) 0.23037(5) 0.01307(17) Uani 1 1 d . . . . .
H5 H 1.061878 0.426993 0.229498 0.016 Uiso 1 1 calc R . . . .
C6 C 0.92801(7) 0.36250(12) 0.29943(5) 0.01338(17) Uani 1 1 d . . . . .
H6 H 0.958476 0.416204 0.345478 0.016 Uiso 1 1 calc R . . . .
H1 H 0.8051(15) 0.273(2) 0.4097(11) 0.032(4) Uiso 1 1 d . . . . .
H1A H 1.0912(15) 0.311(2) 0.1075(9) 0.028(4) Uiso 1 1 d . . . . .

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
O2 0.0139(3) 0.0434(5) 0.0124(3) -0.0004(3) -0.0021(2) -0.0047(3)
O1 0.0117(3) 0.0312(4) 0.0105(3) 0.0001(2) 0.0017(2) -0.0009(3)
C2 0.0094(3) 0.0176(4) 0.0129(3) 0.0011(3) -0.0003(3) -0.0010(3)
C4 0.0096(3) 0.0164(4) 0.0107(3) 0.0013(3) 0.0001(3) 0.0003(3)
N1 0.0093(3) 0.0239(4) 0.0107(3) 0.0009(3) 0.0004(2) -0.0013(3)
C1 0.0107(3) 0.0164(4) 0.0109(3) 0.0009(3) 0.0009(3) 0.0015(3)
C3 0.0104(3) 0.0178(4) 0.0116(3) 0.0001(3) -0.0010(3) -0.0009(3)
C7 0.0128(4) 0.0205(4) 0.0118(4) 0.0011(3) 0.0005(3) -0.0001(3)
C8 0.0149(4) 0.0297(5) 0.0142(4) 0.0006(3) 0.0039(3) -0.0007(3)
C5 0.0106(3) 0.0156(3) 0.0130(4) 0.0005(3) -0.0010(3) -0.0015(3)
C6 0.0120(3) 0.0162(4) 0.0120(3) -0.0005(3) -0.0016(3) -0.0006(3)

_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
O2 C7 1.2374(11) . ?
O1 C1 1.3709(10) . ?
O1 H1 0.873(19) . ?
C2 H2 0.9500 . ?
C2 C1 1.3912(12) . ?
C2 C3 1.3955(12) . ?
C4 N1 1.4190(11) . ?
C4 C3 1.3979(12) . ?
C4 C5 1.3963(11) . ?
N1 C7 1.3487(11) . ?
N1 H1A 0.899(17) . ?
C1 C6 1.3943(12) . ?
C3 H3 0.9500 . ?
C7 C8 1.5096(13) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.3881(11) . ?
C6 H6 0.9500 . ?

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
C1 O1 H1 111.2(11) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.43(8) . . ?
C3 C2 H2 119.8 . . ?
C3 C4 N1 124.20(8) . . ?
C5 C4 N1 116.30(7) . . ?
C5 C4 C3 119.45(8) . . ?
C4 N1 H1A 113.9(10) . . ?
C7 N1 C4 129.03(8) . . ?
C7 N1 H1A 116.9(10) . . ?
O1 C1 C2 119.00(8) . . ?
O1 C1 C6 121.31(8) . . ?
C2 C1 C6 119.69(8) . . ?
C2 C3 C4 119.80(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O2 C7 N1 123.07(8) . . ?
O2 C7 C8 122.60(8) . . ?
N1 C7 C8 114.32(8) . . ?
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 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.53(8) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.02(8) . . ?
C5 C6 H6 120.0 . . ?

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 C1 C6 C5 177.97(8) . . . . ?
C2 C1 C6 C5 -2.63(13) . . . . ?
C4 N1 C7 O2 0.85(16) . . . . ?
C4 N1 C7 C8 -178.47(8) . . . . ?
C4 C5 C6 C1 0.48(13) . . . . ?
N1 C4 C3 C2 174.97(8) . . . . ?
N1 C4 C5 C6 -175.43(8) . . . . ?
C1 C2 C3 C4 0.02(13) . . . . ?
C3 C2 C1 O1 -178.21(8) . . . . ?
C3 C2 C1 C6 2.38(13) . . . . ?
C3 C4 N1 C7 16.98(14) . . . . ?
C3 C4 C5 C6 1.92(13) . . . . ?
C5 C4 N1 C7 -165.80(9) . . . . ?
C5 C4 C3 C2 -2.17(13) . . . . ?

_shelx_res_file                  
;
TITL SIR92 run in space group P b c a
    mo_x8_17151.res
    created by SHELXL-2016/6 at 19:35:20 on 04-Jan-2018
CELL 0.71073 11.7678 7.1966 17.1615 90 90 90
ZERR 8 0.0007 0.0005 0.0011 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 64 72 8 16

L.S. 50
PLAN  5
TEMP -173.1
BOND $H
CONF
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\mo_X8_17151.hkl">
REM </olex2.extras>

WGHT    0.059700    0.619200
FVAR       0.09650
O2    4    0.893760    0.229846   -0.002156    11.00000    0.01386    0.04337 =
         0.01237   -0.00042   -0.00210   -0.00471
O1    4    0.760887    0.262953    0.369088    11.00000    0.01172    0.03117 =
         0.01049    0.00011    0.00169   -0.00092
C2    1    0.775598    0.205221    0.232907    11.00000    0.00943    0.01759 =
         0.01292    0.00108   -0.00027   -0.00103
AFIX  43
H2    2    0.701992    0.151035    0.233655    11.00000   -1.20000
AFIX   0
C4    1    0.945036    0.292118    0.162161    11.00000    0.00963    0.01641 =
         0.01066    0.00132    0.00009    0.00033
N1    3    1.017480    0.293635    0.096066    11.00000    0.00935    0.02388 =
         0.01069    0.00086    0.00040   -0.00133
C1    1    0.821764    0.276835    0.301228    11.00000    0.01073    0.01643 =
         0.01092    0.00091    0.00087    0.00153
C3    1    0.836704    0.212460    0.163282    11.00000    0.01039    0.01779 =
         0.01161    0.00007   -0.00103   -0.00095
AFIX  43
H3    2    0.804777    0.163401    0.116786    11.00000   -1.20000
AFIX   0
C7    1    0.991420    0.263289    0.020598    11.00000    0.01280    0.02049 =
         0.01185    0.00113    0.00055   -0.00014
C8    1    1.091868    0.271289   -0.034007    11.00000    0.01490    0.02971 =
         0.01425    0.00055    0.00385   -0.00068
AFIX 137
H8A   2    1.120433    0.145272   -0.043209    11.00000   -1.50000
H8B   2    1.152067    0.347124   -0.010646    11.00000   -1.50000
H8C   2    1.068317    0.326667   -0.083614    11.00000   -1.50000
AFIX   0
C5    1    0.989271    0.369326    0.230366    11.00000    0.01061    0.01556 =
         0.01304    0.00051   -0.00098   -0.00148
AFIX  43
H5    2    1.061878    0.426993    0.229498    11.00000   -1.20000
AFIX   0
C6    1    0.928008    0.362498    0.299427    11.00000    0.01198    0.01617 =
         0.01198   -0.00053   -0.00158   -0.00058
AFIX  43
H6    2    0.958476    0.416204    0.345478    11.00000   -1.20000
AFIX   0
H1    2    0.805073    0.273291    0.409747    11.00000    0.03233
H1A   2    1.091197    0.311434    0.107541    11.00000    0.02791
HKLF 4




REM  SIR92 run in space group P b c a
REM R1 =  0.0386 for    2198 Fo > 4sig(Fo)  and  0.0417 for all    2436 data
REM    109 parameters refined using      0 restraints

END

WGHT      0.0597      0.6192

REM Highest difference peak  0.448,  deepest hole -0.266,  1-sigma level  0.077
Q1    1   0.7971  0.2403  0.2670  11.00000  0.05    0.45
Q2    1   0.9536  0.3761  0.2644  11.00000  0.05    0.41
Q3    1   0.8082  0.2177  0.1973  11.00000  0.05    0.40
Q4    1   0.9649  0.3282  0.1975  11.00000  0.05    0.39
Q5    1   1.0030  0.2831  0.0599  11.00000  0.05    0.35
;
_shelx_res_checksum              7649
_olex2_submission_special_instructions 'No special instructions were received'
