#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:59:19 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/27/7232755.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7232755
loop_
_publ_author_name
'Ward, Martin R.'
'Oswald, Iain D. H.'
_publ_section_title
;
 Antisolvent addition at extreme conditions
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4437
_journal_paper_doi               10.1039/C9CE00365G
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_name_common            paracetamol
_chemical_name_systematic        acetaminophen
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-24 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.143(8)
_cell_length_b                   11.806(6)
_cell_length_c                   7.399(10)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      3.45
_cell_volume                     1497(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker, Apex3'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.278
_diffrn_measured_fraction_theta_max 0.278
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1289
_diffrn_reflns_av_unetI/netI     0.1386
_diffrn_reflns_Laue_measured_fraction_full 0.278
_diffrn_reflns_Laue_measured_fraction_max 0.278
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            866
_diffrn_reflns_point_group_measured_fraction_full 0.278
_diffrn_reflns_point_group_measured_fraction_max 0.278
_diffrn_reflns_theta_full        23.355
_diffrn_reflns_theta_max         23.355
_diffrn_reflns_theta_min         3.451
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0969 before and 0.0605 after correction. The Ratio of minimum to maximum transmission is 0.7071. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'crystallization at approx 0.21 GPa pressure in MeOH:H2O solution'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         304
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0683
_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)+(0.1041P)²+1.2679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.2071
_reflns_Friedel_coverage         0.000
_reflns_number_gt                161
_reflns_number_total             304
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    02gg_ambient_formii.res created by SHELXL-2014/7

TITL 02gg_ambient_formii_a.res in Pbca
REM Old TITL 02gg_ambient_FormII in Pbca
REM SHELXT solution in Pbca
REM R1 0.416, Rweak 0.009, Alpha 0.821, Orientation as input
REM Formula found by SHELXT: C11 N3 O
CELL 0.71073 17.1432 11.8058 7.3985 90 90 90
ZERR 8 0.0079 0.0055 0.0104 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N O
UNIT 64 72 8 16
RIGU
 
L.S. 50 0 0
PLAN  20
TEMP 23
BOND $H
list 4
fmap 2 53
acta
OMIT 8 8 0
OMIT 8 1 1
REM <olex2.extras>
REM <HklSrc "%.\\02gg_ambient_FormII.hkl">
REM </olex2.extras>
 
WGHT    0.104100    1.267900
FVAR       0.99483
O1    4    0.631974    0.237005    0.244537    11.00000    0.03558    0.04024 =
         0.11687   -0.00928   -0.00487    0.01062
AFIX 147
H1    2    0.595502    0.206644    0.191668    11.00000   -1.50000
AFIX   0
O2    4    1.003102    0.103442    0.267524    11.00000    0.03145    0.03802 =
         0.17376   -0.01438   -0.00853   -0.00432
N1    3    0.906555   -0.018381    0.198616    11.00000    0.02899    0.03252 =
         0.14488   -0.00632   -0.01270   -0.00135
AFIX  43
H1A   2    0.897925   -0.087177    0.166050    11.00000   -1.20000
AFIX  66
C6    1    0.772792    0.011407    0.119931    11.00000    0.02753    0.03027 =
         0.11561   -0.00320    0.00123   -0.00352
AFIX  43
H6    2    0.774668   -0.058661    0.062650    11.00000   -1.20000
AFIX  65
C1    1    0.839456    0.055499    0.200468    11.00000    0.02918    0.02579 =
         0.12650   -0.00155   -0.00467   -0.00253
C2    1    0.836651    0.160223    0.286081    11.00000    0.03751    0.02434 =
         0.12821   -0.00323   -0.00761   -0.00245
AFIX  43
H2    2    0.881254    0.189724    0.339966    11.00000   -1.20000
AFIX  65
C3    1    0.767183    0.220856    0.291159    11.00000    0.03704    0.03290 =
         0.11094    0.00703   -0.00486    0.00113
AFIX  43
H3    2    0.765307    0.290923    0.348440    11.00000   -1.20000
AFIX  65
C4    1    0.700518    0.176765    0.210623    11.00000    0.03218    0.02642 =
         0.09332    0.00988    0.00193    0.00130
C5    1    0.703321    0.072041    0.125009    11.00000    0.03300    0.02989 =
         0.09665    0.00957    0.00786   -0.00514
AFIX  43
H5    2    0.658718    0.042540    0.071125    11.00000   -1.20000
AFIX   0
C7    1    0.980431    0.006510    0.241088    11.00000    0.02506    0.03554 =
         0.11734   -0.00492   -0.00402    0.00344
C8    1    1.035936   -0.093059    0.223461    11.00000    0.02627    0.04642 =
         0.17312   -0.01744   -0.01607    0.01758
AFIX 137
H8A   2    1.079953   -0.071295    0.151155    11.00000   -1.50000
H8B   2    1.009437   -0.155269    0.166787    11.00000   -1.50000
H8C   2    1.053522   -0.115582    0.341294    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  02gg_ambient_formii_a.res in Pbca
REM R1 =  0.0683 for     161 Fo > 4sig(Fo)  and  0.1488 for all     304 data
REM     90 parameters refined using     75 restraints
 
END  
     
WGHT      0.1041      1.2684 

REM Highest difference peak  0.139,  deepest hole -0.131,  1-sigma level  0.038
Q1    1   0.8836  0.1968  0.0729  11.00000  0.05    0.14
Q2    1   0.9793 -0.1640  0.2527  11.00000  0.05    0.13
Q3    1   0.9820 -0.1757  0.1463  11.00000  0.05    0.13
Q4    1   0.8629 -0.1627  0.1413  11.00000  0.05    0.12
Q5    1   0.9979 -0.1945  0.0844  11.00000  0.05    0.12
Q6    1   0.6583 -0.0001  0.1903  11.00000  0.05    0.11
Q7    1   1.1409 -0.1196  0.2406  11.00000  0.05    0.10
Q8    1   0.9010 -0.1067 -0.0755  11.00000  0.05    0.10
Q9    1   1.0810 -0.1795  0.4675  11.00000  0.05    0.10
Q10   1   0.7903 -0.1074  0.2248  11.00000  0.05    0.09
Q11   1   0.7952 -0.1128  0.1632  11.00000  0.05    0.09
Q12   1   0.9496  0.2217  0.2961  11.00000  0.05    0.09
Q13   1   0.6466  0.0375 -0.0405  11.00000  0.05    0.09
Q14   1   0.7670  0.3405  0.2314  11.00000  0.05    0.08
Q15   1   1.1561 -0.1206  0.3552  11.00000  0.05    0.08
Q16   1   0.8396  0.0660  0.3712  11.00000  0.05    0.08
Q17   1   0.7000  0.1203  0.1036  11.00000  0.05    0.08
Q18   1   0.9972  0.1484  0.1511  11.00000  0.05    0.08
Q19   1   0.7129  0.1584  0.2291  11.00000  0.05    0.07
Q20   1   0.7420  0.2386  0.2372  11.00000  0.05    0.07

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0683 for 161 Fo > 4sig(Fo) and 0.1488 for all 1076 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.14, deepest hole -0.13
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1488
  REM R1_gt = 0.0683
  REM wR_ref = 0.2071
  REM GOOF = 1.082
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1076
  REM Reflections_gt = 161
  REM Parameters = n/a
  REM Hole = -0.13
  REM Peak = 0.14
  REM Flack = n/a

  
;
_cod_data_source_file            c9ce00365g1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7232755--7232759.cif.'
_cod_database_code               7232755
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C6(H6), C2(H2), C3(H3), C5(H5)
3.b Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Crystal in diamond anvil cell in MeOH:H2O paracetamol solution'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O1 O 0.6320(4) 0.2370(6) 0.245(5) 0.064(12) Uani 1 1 d . U
H1 H 0.5955 0.2066 0.1917 0.096 Uiso 1 1 calc GR .
O2 O 1.0031(4) 0.1034(6) 0.268(4) 0.081(16) Uani 1 1 d . U
N1 N 0.9066(6) -0.0184(7) 0.199(3) 0.069(13) Uani 1 1 d . U
H1A H 0.8979 -0.0872 0.1660 0.083 Uiso 1 1 calc R .
C6 C 0.7728(5) 0.0114(5) 0.120(3) 0.058(11) Uani 1 1 d . U
H6 H 0.7747 -0.0587 0.0627 0.069 Uiso 1 1 calc R .
C1 C 0.8395(4) 0.0555(5) 0.200(3) 0.060(12) Uani 1 1 d G U
C2 C 0.8367(5) 0.1602(6) 0.286(3) 0.063(12) Uani 1 1 d G U
H2 H 0.8813 0.1897 0.3400 0.076 Uiso 1 1 calc R .
C3 C 0.7672(5) 0.2209(5) 0.291(2) 0.060(12) Uani 1 1 d G U
H3 H 0.7653 0.2909 0.3484 0.072 Uiso 1 1 calc R .
C4 C 0.7005(4) 0.1768(5) 0.211(3) 0.051(10) Uani 1 1 d G U
C5 C 0.7033(4) 0.0720(5) 0.125(2) 0.053(11) Uani 1 1 d G U
H5 H 0.6587 0.0425 0.0711 0.064 Uiso 1 1 calc R .
C7 C 0.9804(7) 0.0065(8) 0.241(5) 0.059(17) Uani 1 1 d . U
C8 C 1.0359(9) -0.0931(10) 0.223(6) 0.08(3) Uani 1 1 d . U
H8A H 1.0800 -0.0713 0.1512 0.123 Uiso 1 1 calc GR .
H8B H 1.0094 -0.1553 0.1668 0.123 Uiso 1 1 calc GR .
H8C H 1.0535 -0.1156 0.3413 0.123 Uiso 1 1 calc GR .
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
O1 0.036(5) 0.040(4) 0.12(4) -0.009(8) -0.005(11) 0.011(4)
O2 0.031(6) 0.038(4) 0.17(5) -0.014(8) -0.009(12) -0.004(3)
N1 0.029(5) 0.033(4) 0.14(4) -0.006(8) -0.013(10) -0.001(3)
C6 0.028(6) 0.030(5) 0.12(3) -0.003(9) 0.001(9) -0.004(4)
C1 0.029(6) 0.026(4) 0.13(4) -0.002(10) -0.005(9) -0.003(3)
C2 0.038(7) 0.024(4) 0.13(4) -0.003(9) -0.008(10) -0.002(4)
C3 0.037(7) 0.033(5) 0.11(4) 0.007(9) -0.005(11) 0.001(4)
C4 0.032(7) 0.026(4) 0.09(3) 0.010(8) 0.002(9) 0.001(4)
C5 0.033(7) 0.030(4) 0.10(3) 0.010(8) 0.008(9) -0.005(4)
C7 0.025(6) 0.036(5) 0.12(5) -0.005(11) -0.004(11) 0.003(4)
C8 0.026(7) 0.046(6) 0.17(8) -0.017(13) -0.016(16) 0.018(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 H1 109.5
C1 N1 H1A 115.9
C7 N1 H1A 115.9
C7 N1 C1 128.3(9)
C1 C6 H6 120.0
C1 C6 C5 120.0
C5 C6 H6 120.0
C6 C1 N1 115.1(8)
C6 C1 C2 120.0
C2 C1 N1 124.7(8)
C1 C2 H2 120.0
C3 C2 C1 120.0
C3 C2 H2 120.0
C2 C3 H3 120.0
C4 C3 C2 120.0
C4 C3 H3 120.0
C3 C4 O1 115.1(11)
C5 C4 O1 124.3(9)
C5 C4 C3 120.0
C6 C5 H5 120.0
C4 C5 C6 120.0
C4 C5 H5 120.0
O2 C7 N1 122.9(10)
O2 C7 C8 122.6(11)
N1 C7 C8 113.8(12)
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 0.8200
O1 C4 1.396(11)
O2 C7 1.224(13)
N1 H1A 0.8600
N1 C1 1.444(11)
N1 C7 1.338(17)
C6 H6 0.9300
C6 C1 1.3900
C6 C5 1.3900
C1 C2 1.3900
C2 H2 0.9300
C2 C3 1.3900
C3 H3 0.9300
C3 C4 1.3900
C4 C5 1.3900
C5 H5 0.9300
C7 C8 1.518(14)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
