#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:59:19 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/27/7232757.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_7232757
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
_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                   17.1202(17)
_cell_length_b                   11.7968(11)
_cell_length_c                   7.288(2)
_cell_measurement_reflns_used    695
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.91
_cell_measurement_theta_min      2.38
_cell_volume                     1471.9(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.387
_diffrn_measured_fraction_theta_max 0.387
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.387
_diffrn_reflns_Laue_measured_fraction_max 0.387
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_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            4019
_diffrn_reflns_point_group_measured_fraction_full 0.387
_diffrn_reflns_point_group_measured_fraction_max 0.387
_diffrn_reflns_theta_full        23.320
_diffrn_reflns_theta_max         23.320
_diffrn_reflns_theta_min         2.379
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1466 before and 0.0755 after correction. The Ratio of minimum to maximum transmission is 0.8510. 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    1.364
_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         0.132
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         413
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0579
_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)+(0.0826P)²+0.4551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                271
_reflns_number_total             413
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    orthop.res created by SHELXL-2014/7

TITL orthoP in Pbca
CELL 0.71073 17.1202 11.7968 7.2879 90 90 90
ZERR 8 0.0017 0.0011 0.0023 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
PLAN  20
SIZE 0.09 0.07 0.05
TEMP 23
fmap 2 53
ACTA
OMIT 8 7 2
OMIT 10 2 2
REM <olex2.extras>
REM <HklSrc "%.\\orthoP.hkl">
REM </olex2.extras>
 
WGHT    0.082600    0.455100
FVAR       0.39075
O1    4    0.632572    0.238199    0.235901    11.00000    0.03072    0.03648 =
         0.09086    0.00232    0.00343    0.00466
AFIX 147
H1    2    0.595214    0.195989    0.218875    11.00000   -1.50000
AFIX   0
O2    4    1.003667    0.102847    0.270469    11.00000    0.03417    0.04104 =
         0.10320   -0.00578   -0.00418   -0.00522
N1    3    0.905608   -0.018570    0.205779    11.00000    0.03093    0.02202 =
         0.09653   -0.00381   -0.00215    0.00295
AFIX  43
H1A   2    0.896008   -0.088615    0.182093    11.00000   -1.20000
AFIX  66
C6    1    0.771819    0.011021    0.125633    11.00000    0.03708    0.02483 =
         0.06552   -0.00359   -0.00031   -0.00238
AFIX  43
H6    2    0.772991   -0.059537    0.068780    11.00000   -1.20000
AFIX  65
C1    1    0.839319    0.055113    0.203984    11.00000    0.02912    0.02591 =
         0.04539    0.00702    0.01101   -0.00231
C2    1    0.837567    0.160571    0.288958    11.00000    0.03208    0.02636 =
         0.06573   -0.00049   -0.00265   -0.00296
AFIX  43
H2    2    0.882730    0.190071    0.341380    11.00000   -1.20000
AFIX  65
C3    1    0.768315    0.221936    0.295580    11.00000    0.03973    0.02667 =
         0.06300    0.00630    0.00009   -0.00174
AFIX  43
H3    2    0.767143    0.292494    0.352433    11.00000   -1.20000
AFIX  65
C4    1    0.700814    0.177845    0.217229    11.00000    0.03187    0.02555 =
         0.06794    0.00226   -0.00099    0.00123
C5    1    0.702564    0.072388    0.132255    11.00000    0.03311    0.03237 =
         0.07100   -0.00005    0.00462   -0.00560
AFIX  43
H5    2    0.657402    0.042888    0.079833    11.00000   -1.20000
AFIX   0
C7    1    0.980673    0.006384    0.239269    11.00000    0.03581    0.03707 =
         0.04910    0.01051    0.00470    0.00232
C8    1    1.035166   -0.093495    0.226435    11.00000    0.04102    0.03909 =
         0.06692    0.00805    0.00052    0.01010
AFIX 137
H8A   2    1.085929   -0.067979    0.188682    11.00000   -1.50000
H8B   2    1.015319   -0.146643    0.138249    11.00000   -1.50000
H8C   2    1.038992   -0.129541    0.344191    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  orthoP in Pbca
REM R1 =  0.0579 for     271 Fo > 4sig(Fo)  and  0.0955 for all     413 data
REM     90 parameters refined using     75 restraints
 
END  
     
WGHT      0.0826      0.4551 

REM Highest difference peak  0.132,  deepest hole -0.149,  1-sigma level  0.035
Q1    1   0.8189  0.1828  0.0558  11.00000  0.05    0.13
Q2    1   0.9829 -0.2437  0.3977  11.00000  0.05    0.12
Q3    1   0.8150  0.0783  0.4384  11.00000  0.05    0.12
Q4    1   1.0004 -0.1645  0.1841  11.00000  0.05    0.12
Q5    1   1.1054 -0.1221  0.1178  11.00000  0.05    0.11
Q6    1   0.7000  0.1410  0.2319  11.00000  0.05    0.10
Q7    1   0.8138  0.0249  0.1455  11.00000  0.05    0.10
Q8    1   0.7035  0.0481  0.3120  11.00000  0.05    0.10
Q9    1   0.7070  0.1785  0.4178  11.00000  0.05    0.10
Q10   1   0.8187  0.0801 -0.0544  11.00000  0.05    0.10
Q11   1   0.8476 -0.1625  0.0665  11.00000  0.05    0.09
Q12   1   1.0595 -0.1633 -0.0816  11.00000  0.05    0.09
Q13   1   0.8602  0.0174  0.2936  11.00000  0.05    0.09
Q14   1   0.7054  0.1561  0.3208  11.00000  0.05    0.09
Q15   1   0.5998  0.3261  0.3458  11.00000  0.05    0.09
Q16   1   0.8075  0.1818  0.5226  11.00000  0.05    0.09
Q17   1   0.8634  0.2471  0.4616  11.00000  0.05    0.08
Q18   1   0.8842 -0.1065  0.0685  11.00000  0.05    0.07
Q19   1   0.8588  0.2024  0.2751  11.00000  0.05    0.07
Q20   1   1.0645 -0.0594  0.4814  11.00000  0.05    0.07

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0579 for 271 Fo > 4sig(Fo) and 0.0955 for all 5037 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.13, deepest hole -0.15
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0955
  REM R1_gt = 0.0579
  REM wR_ref = 0.1470
  REM GOOF = 1.076
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 5037
  REM Reflections_gt = 271
  REM Parameters = n/a
  REM Hole = -0.15
  REM Peak = 0.13
  REM Flack = n/a

  
;
_cod_data_source_file            c9ce00365g1.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7232755--7232759.cif.'
_cod_database_code               7232757
_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.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.991
_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 0.63257(17) 0.2382(3) 0.2359(19) 0.053(5) Uani 1 1 d . U
H1 H 0.5952 0.1960 0.2189 0.079 Uiso 1 1 calc GR .
O2 O 1.00367(18) 0.1028(3) 0.2705(15) 0.059(7) Uani 1 1 d . U
N1 N 0.9056(2) -0.0186(3) 0.2058(15) 0.050(6) Uani 1 1 d . U
H1A H 0.8960 -0.0886 0.1821 0.060 Uiso 1 1 calc R .
C6 C 0.77182(17) 0.0110(3) 0.1256(12) 0.042(6) Uani 1 1 d . U
H6 H 0.7730 -0.0595 0.0688 0.051 Uiso 1 1 calc R .
C1 C 0.83932(13) 0.0551(2) 0.2040(12) 0.033(6) Uani 1 1 d G U
C2 C 0.83757(14) 0.1606(3) 0.2890(11) 0.041(6) Uani 1 1 d G U
H2 H 0.8827 0.1901 0.3414 0.050 Uiso 1 1 calc R .
C3 C 0.76831(16) 0.2219(3) 0.2956(11) 0.043(7) Uani 1 1 d G U
H3 H 0.7671 0.2925 0.3524 0.052 Uiso 1 1 calc R .
C4 C 0.70081(12) 0.1778(2) 0.2172(12) 0.042(6) Uani 1 1 d G U
C5 C 0.70256(14) 0.0724(3) 0.1323(11) 0.045(6) Uani 1 1 d G U
H5 H 0.6574 0.0429 0.0798 0.055 Uiso 1 1 calc R .
C7 C 0.9807(3) 0.0064(5) 0.239(2) 0.041(9) Uani 1 1 d . U
C8 C 1.0352(3) -0.0935(5) 0.226(2) 0.049(11) Uani 1 1 d . U
H8A H 1.0859 -0.0680 0.1887 0.074 Uiso 1 1 calc GR .
H8B H 1.0153 -0.1466 0.1382 0.074 Uiso 1 1 calc GR .
H8C H 1.0390 -0.1295 0.3442 0.074 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 0.0307(17) 0.0365(19) 0.091(17) 0.002(4) 0.003(4) 0.0047(15)
O2 0.0342(19) 0.041(2) 0.10(2) -0.006(4) -0.004(4) -0.0052(16)
N1 0.031(2) 0.0220(19) 0.10(2) -0.004(4) -0.002(4) 0.0030(16)
C6 0.037(2) 0.025(2) 0.066(19) -0.004(5) 0.000(4) -0.002(2)
C1 0.029(2) 0.026(2) 0.045(17) 0.007(5) 0.011(4) -0.0023(19)
C2 0.032(2) 0.026(2) 0.066(19) 0.000(5) -0.003(4) -0.003(2)
C3 0.040(3) 0.027(3) 0.06(2) 0.006(5) 0.000(4) -0.002(2)
C4 0.032(2) 0.026(2) 0.068(18) 0.002(5) -0.001(4) 0.001(2)
C5 0.033(3) 0.032(2) 0.071(19) 0.000(5) 0.005(4) -0.006(2)
C7 0.036(3) 0.037(3) 0.05(3) 0.011(5) 0.005(5) 0.002(2)
C8 0.041(3) 0.039(3) 0.07(4) 0.008(5) 0.001(6) 0.010(2)
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
C7 N1 C1 129.0(4)
C1 C6 C5 120.0
C6 C1 N1 115.9(3)
C6 C1 C2 120.0
C2 C1 N1 123.9(4)
C1 C2 C3 120.0
C2 C3 C4 120.0
O1 C4 C3 118.2(4)
O1 C4 C5 121.7(4)
C3 C4 C5 120.0
C4 C5 C6 120.0
O2 C7 N1 123.1(5)
O2 C7 C8 122.6(5)
N1 C7 C8 114.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.375(4)
O2 C7 1.225(7)
N1 C1 1.430(4)
N1 C7 1.341(7)
C6 C1 1.3900
C6 C5 1.3900
C1 C2 1.3900
C2 C3 1.3900
C3 C4 1.3900
C4 C5 1.3900
C7 C8 1.506(7)
