####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1902442'
loop_
_audit_author_name
_audit_author_address
'Iain D H Oswald '
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
#data_02gg_ambient_formii
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            paracetamol
_chemical_name_systematic        acetaminophen
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          ?
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, 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'

_cell_length_a                   17.143(8)
_cell_length_b                   11.806(6)
_cell_length_c                   7.399(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1497(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    120
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                161
_reflns_number_total             304
_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       '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)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      0.949
_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
_refine_special_details          
'RIGU restraint applied.  High pressure dataset'
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.6320(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 . . . .


_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 0.8200 . ?
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 . ?

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
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 . . ?

_olex2_exptl_crystal_mounting_method 
'Crystal in diamond anvil cell in MeOH:H2O paracetamol solution'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1902445'
loop_
_audit_author_name
_audit_author_address
'Iain D H Oswald '
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
#data_monop
_audit_creation_date             2019-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'paracetamol:methanol solvate, (1:1)'
_chemical_name_systematic        'acetaminophen:methanol solvate'
_chemical_formula_moiety         'C H4 O, C8 H9 N O2'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9717(15)
_cell_length_b                   17.1881(9)
_cell_length_c                   13.0437(19)
_cell_angle_alpha                90
_cell_angle_beta                 116.032(8)
_cell_angle_gamma                90
_cell_volume                     2613.2(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      22.360
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0848 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9145. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method 
'Compresion of a 0.05 g/g solution in 64% aqueous methanol. Compression to 1.5 GPa to initiate the crystallisation followed by decompression 0.7 GPa and heat treatment'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.349
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9591
_diffrn_reflns_point_group_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.349
_diffrn_reflns_theta_full        23.297
_diffrn_reflns_theta_max         23.297
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.349
_diffrn_measured_fraction_theta_max 0.349
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'Sample housed in a diamond anvil cell.'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                765
_reflns_number_total             1319
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.552
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.1291
_refine_ls_restrained_S_all      1.552
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3349
_refine_ls_wR_factor_ref         0.4172
_refine_special_details          
'A number of reflections were omitted due to the shading of the diamond anvil cell.  The atoms remain isotropic due to the low completeness of the data. weighting scheme did not suggest any more suitable weights.'
_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:
 N1C(H1CA), N1A(H1AA), N1B(H1BA), C5A(H5A), C6A(H6A), C2A(H2A), C3A(H3A),
 C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B)
3.b Fitted hexagon refined as free rotating group:
 C4A(C5A,C6A,C1A,C2A,C3A), C1C(C2C,C3C,C4C,C5C,C6C), C1B(C2B,C3B,C4B,C5B,C6B)
3.c Tetrahedral OH refined with riding coordinates:
 O3C(H3CA), O3A(H3AA), O3B(H3BA)
3.d Idealised Me refined as rotating group:
 C9C(H9CA,H9CB,H9CC), C8C(H8CA,H8CB,H8CC), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,
 H8AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
3.e Idealised tetrahedral OH refined as rotating group:
 O1C(H1C), O1B(H1B), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3C O 1.2510(7) 0.4161(4) 0.8549(12) 0.035(2) Uiso 1 1 d . U . . .
H3CA H 1.247241 0.449625 0.808598 0.053 Uiso 1 1 calc R . . . .
O2C O 0.7774(7) 0.4759(4) 0.3059(13) 0.032(2) Uiso 1 1 d . U . . .
O1C O 1.1211(8) 0.2931(4) 0.7745(12) 0.032(2) Uiso 1 1 d . U . . .
H1C H 1.176361 0.320636 0.784690 0.048 Uiso 1 1 calc GR . . . .
O1B O 0.5158(8) 0.3000(4) 0.5125(13) 0.038(2) Uiso 1 1 d . U . . .
H1B H 0.573808 0.321402 0.516158 0.056 Uiso 1 1 calc GR . . . .
O2B O 0.1617(7) 0.4752(3) 0.0464(12) 0.028(2) Uiso 1 1 d . U . . .
O2A O 0.6243(7) 0.5286(4) 0.4230(13) 0.032(2) Uiso 1 1 d . U . . .
O3A O 0.1264(9) 0.5960(4) -0.1049(15) 0.057(3) Uiso 1 1 d . U . . .
H3AA H 0.131562 0.557588 -0.065663 0.086 Uiso 1 1 calc R . . . .
O1A O 0.2851(8) 0.7006(4) -0.0530(13) 0.040(2) Uiso 1 1 d . U . . .
H1A H 0.236251 0.666302 -0.071909 0.059 Uiso 1 1 calc GR . . . .
O3B O 0.6533(8) 0.4193(4) 0.5844(13) 0.041(3) Uiso 1 1 d . U . . .
H3BA H 0.650838 0.453044 0.538985 0.062 Uiso 1 1 calc R . . . .
N1C N 0.7416(8) 0.3589(4) 0.3666(14) 0.027(3) Uiso 1 1 d . U . . .
H1CA H 0.690652 0.322865 0.348593 0.033 Uiso 1 1 calc R . . . .
N1A N 0.6565(8) 0.6450(4) 0.3674(14) 0.023(2) Uiso 1 1 d . U . . .
H1AA H 0.702799 0.683973 0.389314 0.027 Uiso 1 1 calc R . . . .
C9C C 1.3550(12) 0.4231(8) 0.952(2) 0.043(4) Uiso 1 1 d . U . . .
H9CA H 1.417235 0.419042 0.931642 0.065 Uiso 1 1 calc GR . . . .
H9CB H 1.361117 0.382272 1.005038 0.065 Uiso 1 1 calc GR . . . .
H9CC H 1.358208 0.472627 0.987591 0.065 Uiso 1 1 calc GR . . . .
N1B N 0.1455(8) 0.3499(4) 0.0891(14) 0.030(3) Uiso 1 1 d . U . . .
H1BA H 0.105154 0.308393 0.064208 0.036 Uiso 1 1 calc R . . . .
C8C C 0.5999(10) 0.4116(6) 0.193(2) 0.025(3) Uiso 1 1 d . U . . .
H8CA H 0.550247 0.450500 0.199955 0.038 Uiso 1 1 calc GR . . . .
H8CB H 0.569210 0.360894 0.193550 0.038 Uiso 1 1 calc GR . . . .
H8CC H 0.605206 0.419012 0.122398 0.038 Uiso 1 1 calc GR . . . .
C9A C 0.0302(14) 0.5885(7) -0.210(2) 0.051(4) Uiso 1 1 d . U . . .
H9AA H 0.046420 0.551861 -0.256933 0.076 Uiso 1 1 calc GR . . . .
H9AB H 0.012127 0.638164 -0.247978 0.076 Uiso 1 1 calc GR . . . .
H9AC H -0.033821 0.570503 -0.198681 0.076 Uiso 1 1 calc GR . . . .
C7C C 0.7163(11) 0.4186(5) 0.290(2) 0.031(3) Uiso 1 1 d . U . . .
C8A C 0.7992(11) 0.5902(6) 0.541(2) 0.031(3) Uiso 1 1 d . U . . .
H8AA H 0.789074 0.579583 0.608367 0.046 Uiso 1 1 calc GR . . . .
H8AB H 0.831003 0.641294 0.546490 0.046 Uiso 1 1 calc GR . . . .
H8AC H 0.850459 0.552409 0.534392 0.046 Uiso 1 1 calc GR . . . .
C7A C 0.6870(10) 0.5859(5) 0.4396(18) 0.026(3) Uiso 1 1 d . U . . .
C4A C 0.3747(6) 0.6822(4) 0.0524(8) 0.029(3) Uiso 1 1 d . U . . .
C5A C 0.4725(7) 0.7280(4) 0.0865(9) 0.030(3) Uiso 1 1 d G U . . .
H5A H 0.475416 0.767704 0.039353 0.037 Uiso 1 1 calc R . . . .
C6A C 0.5660(6) 0.7145(4) 0.1910(10) 0.037(3) Uiso 1 1 d G U . . .
H6A H 0.631493 0.745071 0.213747 0.045 Uiso 1 1 calc R . . . .
C1A C 0.5617(7) 0.6551(4) 0.2614(9) 0.028(3) Uiso 1 1 d G U . . .
C2A C 0.4639(7) 0.6094(4) 0.2273(9) 0.031(3) Uiso 1 1 d G U . . .
H2A H 0.460957 0.569665 0.274441 0.037 Uiso 1 1 calc R . . . .
C3A C 0.3703(5) 0.6229(4) 0.1228(10) 0.026(3) Uiso 1 1 d G U . . .
H3A H 0.304878 0.592297 0.100047 0.031 Uiso 1 1 calc R . . . .
C1C C 0.8394(6) 0.3485(3) 0.4703(8) 0.018(3) Uiso 1 1 d . U . . .
C2C C 0.9363(6) 0.3956(3) 0.5083(8) 0.019(3) Uiso 1 1 d G U . . .
H2C H 0.937886 0.438196 0.465044 0.023 Uiso 1 1 calc R . . . .
C3C C 1.0306(5) 0.3790(3) 0.6108(10) 0.012(2) Uiso 1 1 d G U . . .
H3C H 1.095426 0.410536 0.636218 0.014 Uiso 1 1 calc R . . . .
C4C C 1.0282(6) 0.3154(4) 0.6754(8) 0.026(3) Uiso 1 1 d G U . . .
C5C C 0.9314(7) 0.2683(4) 0.6375(9) 0.032(3) Uiso 1 1 d G U . . .
H5C H 0.929734 0.225681 0.680728 0.038 Uiso 1 1 calc R . . . .
C6C C 0.8370(5) 0.2848(3) 0.5349(10) 0.029(3) Uiso 1 1 d G U . . .
H6C H 0.772193 0.253340 0.509554 0.034 Uiso 1 1 calc R . . . .
C7B C 0.1113(11) 0.4112(5) 0.019(2) 0.029(3) Uiso 1 1 d . U . . .
C1B C 0.2395(7) 0.3440(3) 0.1991(9) 0.017(3) Uiso 1 1 d . U . . .
C2B C 0.3326(7) 0.3946(3) 0.2389(9) 0.029(3) Uiso 1 1 d G U . . .
H2B H 0.333117 0.437027 0.194900 0.035 Uiso 1 1 calc R . . . .
C3B C 0.4249(6) 0.3818(3) 0.3445(10) 0.023(3) Uiso 1 1 d G U . . .
H3B H 0.487161 0.415588 0.371169 0.028 Uiso 1 1 calc R . . . .
C4B C 0.4241(7) 0.3184(4) 0.4103(9) 0.028(3) Uiso 1 1 d G U . . .
C5B C 0.3310(7) 0.2678(3) 0.3705(9) 0.024(3) Uiso 1 1 d G U . . .
H5B H 0.330532 0.225371 0.414562 0.029 Uiso 1 1 calc R . . . .
C6B C 0.2388(6) 0.2806(3) 0.2649(10) 0.033(3) Uiso 1 1 d G U . . .
H6B H 0.176486 0.246809 0.238293 0.040 Uiso 1 1 calc R . . . .
C8B C 0.0062(10) 0.3997(7) -0.0867(19) 0.037(3) Uiso 1 1 d . U . . .
H8BA H -0.045379 0.442304 -0.097182 0.056 Uiso 1 1 calc GR . . . .
H8BB H -0.029859 0.351918 -0.082257 0.056 Uiso 1 1 calc GR . . . .
H8BC H 0.025206 0.397520 -0.149944 0.056 Uiso 1 1 calc GR . . . .
C9B C 0.7614(11) 0.4230(7) 0.6835(19) 0.036(3) Uiso 1 1 d . U . . .
H9BA H 0.822436 0.420710 0.660793 0.053 Uiso 1 1 calc GR . . . .
H9BB H 0.767892 0.379882 0.732771 0.053 Uiso 1 1 calc GR . . . .
H9BC H 0.766392 0.470840 0.723357 0.053 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
O3C H3CA 0.8200 . ?
O3C C9C 1.394(13) . ?
O2C C7C 1.224(14) . ?
O1C H1C 0.8200 . ?
O1C C4C 1.379(9) . ?
O1B H1B 0.8200 . ?
O1B C4B 1.378(10) . ?
O2B C7B 1.250(11) . ?
O2A C7A 1.235(13) . ?
O3A H3AA 0.8200 . ?
O3A C9A 1.400(17) . ?
O1A H1A 0.8200 . ?
O1A C4A 1.393(11) . ?
O3B H3BA 0.8200 . ?
O3B C9B 1.432(13) . ?
N1C H1CA 0.8600 . ?
N1C C7C 1.36(2) . ?
N1C C1C 1.403(10) . ?
N1A H1AA 0.8600 . ?
N1A C7A 1.32(2) . ?
N1A C1A 1.401(12) . ?
C9C H9CA 0.9600 . ?
C9C H9CB 0.9600 . ?
C9C H9CC 0.9600 . ?
N1B H1BA 0.8600 . ?
N1B C7B 1.33(2) . ?
N1B C1B 1.422(12) . ?
C8C H8CA 0.9600 . ?
C8C H8CB 0.9600 . ?
C8C H8CC 0.9600 . ?
C8C C7C 1.492(16) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C8A C7A 1.478(15) . ?
C4A C5A 1.3900 . ?
C4A C3A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C1A 1.3900 . ?
C1A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9300 . ?
C1C C2C 1.3900 . ?
C1C C6C 1.3900 . ?
C2C H2C 0.9300 . ?
C2C C3C 1.3900 . ?
C3C H3C 0.9300 . ?
C3C C4C 1.3900 . ?
C4C C5C 1.3900 . ?
C5C H5C 0.9300 . ?
C5C C6C 1.3900 . ?
C6C H6C 0.9300 . ?
C7B C8B 1.468(18) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C2B H2B 0.9300 . ?
C2B C3B 1.3900 . ?
C3B H3B 0.9300 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B H5B 0.9300 . ?
C5B C6B 1.3900 . ?
C6B H6B 0.9300 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?

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
C9C O3C H3CA 109.5 . . ?
C4C O1C H1C 109.5 . . ?
C4B O1B H1B 109.5 . . ?
C9A O3A H3AA 109.5 . . ?
C4A O1A H1A 109.5 . . ?
C9B O3B H3BA 109.5 . . ?
C7C N1C H1CA 115.6 . . ?
C7C N1C C1C 128.7(9) . . ?
C1C N1C H1CA 115.6 . . ?
C7A N1A H1AA 114.5 . . ?
C7A N1A C1A 131.1(8) . . ?
C1A N1A H1AA 114.5 . . ?
O3C C9C H9CA 109.5 . . ?
O3C C9C H9CB 109.5 . . ?
O3C C9C H9CC 109.5 . . ?
H9CA C9C H9CB 109.5 . . ?
H9CA C9C H9CC 109.5 . . ?
H9CB C9C H9CC 109.5 . . ?
C7B N1B H1BA 115.6 . . ?
C7B N1B C1B 128.7(8) . . ?
C1B N1B H1BA 115.6 . . ?
H8CA C8C H8CB 109.5 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
C7C C8C H8CA 109.5 . . ?
C7C C8C H8CB 109.5 . . ?
C7C C8C H8CC 109.5 . . ?
O3A C9A H9AA 109.5 . . ?
O3A C9A H9AB 109.5 . . ?
O3A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O2C C7C N1C 123.5(13) . . ?
O2C C7C C8C 123.1(13) . . ?
N1C C7C C8C 113.0(12) . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
O2A C7A N1A 121.3(11) . . ?
O2A C7A C8A 120.7(13) . . ?
N1A C7A C8A 118.0(10) . . ?
C5A C4A O1A 115.9(7) . . ?
C5A C4A C3A 120.0 . . ?
C3A C4A O1A 124.1(7) . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C6A C1A N1A 118.1(8) . . ?
C2A C1A N1A 121.9(8) . . ?
C2A C1A C6A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C2C C1C N1C 124.3(7) . . ?
C2C C1C C6C 120.0 . . ?
C6C C1C N1C 115.7(7) . . ?
C1C C2C H2C 120.0 . . ?
C1C C2C C3C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C2C C3C C4C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
O1C C4C C3C 122.9(7) . . ?
O1C C4C C5C 117.0(7) . . ?
C5C C4C C3C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C6C C5C C4C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
C5C C6C C1C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
O2B C7B N1B 121.8(14) . . ?
O2B C7B C8B 122.5(13) . . ?
N1B C7B C8B 115.5(10) . . ?
C2B C1B N1B 123.5(7) . . ?
C2B C1B C6B 120.0 . . ?
C6B C1B N1B 116.3(7) . . ?
C1B C2B H2B 120.0 . . ?
C3B C2B C1B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
O1B C4B C3B 122.7(7) . . ?
O1B C4B C5B 117.2(6) . . ?
C3B C4B C5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O3B C9B H9BA 109.5 . . ?
O3B C9B H9BB 109.5 . . ?
O3B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1902444'
loop_
_audit_author_name
_audit_author_address
'Iain D H Oswald '
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
#data_orthop
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            paracetamol
_chemical_name_systematic        acetaminophen
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          ?
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, 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'

_cell_length_a                   17.1202(17)
_cell_length_b                   11.7968(11)
_cell_length_c                   7.288(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1471.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    695
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.91
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_special_details          'high-pressure dataset, diamond anvil cell'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                271
_reflns_number_total             413
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      0.995
_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
_refine_special_details          
'AFIX applied to aromatic ring and RIGU restraint applied'
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.63257(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 . . . .


_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 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) . ?

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
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) . . ?

_olex2_exptl_crystal_mounting_method 
'Crystal in diamond anvil cell in MeOH:H2O paracetamol solution'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1902443'
loop_
_audit_author_name
_audit_author_address
'Iain D H Oswald '
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        acetaminophen
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          ?
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      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, 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'

_cell_length_a                   17.1522(5)
_cell_length_b                   11.8201(4)
_cell_length_c                   7.3985(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1499.98(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      68.272
_cell_measurement_theta_min      5.157
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0894 before and 0.0482 after correction. The Ratio of minimum to maximum transmission is 0.8688. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 
'Crystallization performed in large volume press at approx 0.8 GPa.  Crystals obtained from MeOH:H2O mixture approx 60:40 w/w'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15062
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.344
_diffrn_reflns_theta_min         5.157
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1223
_reflns_number_total             1378
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_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)'
_computing_structure_solution    ?
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0080(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1378
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.049
_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)+(0.0624P)²+0.5387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          'RIGU restraints applied'
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.63245(7) 0.23690(10) 0.2306(2) 0.0525(4) Uani 1 1 d . U . . .
H1 H 0.5953 0.1935 0.2219 0.079 Uiso 1 1 calc GR . . . .
O2 O 1.00319(7) 0.10321(11) 0.2719(2) 0.0680(5) Uani 1 1 d . U . . .
N1 N 0.90532(8) -0.01815(11) 0.2088(2) 0.0429(4) Uani 1 1 d . U . . .
H1A H 0.8957 -0.0883 0.1875 0.052 Uiso 1 1 calc R . . . .
C6 C 0.77181(5) 0.01004(6) 0.12953(14) 0.0379(4) Uani 1 1 d . U . . .
H6 H 0.7731 -0.0607 0.0744 0.045 Uiso 1 1 calc R . . . .
C1 C 0.83906(4) 0.05448(7) 0.20663(14) 0.0348(4) Uani 1 1 d G U . . .
C2 C 0.83716(4) 0.16014(7) 0.28900(14) 0.0374(4) Uani 1 1 d G U . . .
H2 H 0.8822 0.1899 0.3406 0.045 Uiso 1 1 calc R . . . .
C3 C 0.76801(5) 0.22135(6) 0.29426(14) 0.0386(4) Uani 1 1 d G U . . .
H3 H 0.7667 0.2920 0.3494 0.046 Uiso 1 1 calc R . . . .
C4 C 0.70075(4) 0.17691(7) 0.21716(15) 0.0366(4) Uani 1 1 d G U . . .
C5 C 0.70265(4) 0.07125(8) 0.13480(14) 0.0384(4) Uani 1 1 d G U . . .
H5 H 0.6577 0.0415 0.0832 0.046 Uiso 1 1 calc R . . . .
C7 C 0.98041(9) 0.00662(14) 0.2392(3) 0.0445(4) Uani 1 1 d . U . . .
C8 C 1.03477(11) -0.09314(17) 0.2303(3) 0.0582(5) Uani 1 1 d . U . . .
H8A H 1.0838 -0.0697 0.1803 0.087 Uiso 1 1 calc GR . . . .
H8B H 1.0123 -0.1508 0.1552 0.087 Uiso 1 1 calc GR . . . .
H8C H 1.0429 -0.1226 0.3498 0.087 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 0.8200 . ?
O1 C4 1.3730(13) . ?
O2 C7 1.231(2) . ?
N1 H1A 0.8600 . ?
N1 C1 1.4243(14) . ?
N1 C7 1.340(2) . ?
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 1.505(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C4 O1 H1 109.5 . . ?
C1 N1 H1A 115.2 . . ?
C7 N1 H1A 115.2 . . ?
C7 N1 C1 129.59(12) . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C1 N1 116.04(8) . . ?
C6 C1 C2 120.0 . . ?
C2 C1 N1 123.73(8) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
O1 C4 C3 118.90(8) . . ?
O1 C4 C5 121.04(8) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
O2 C7 N1 122.74(15) . . ?
O2 C7 C8 122.60(15) . . ?
N1 C7 C8 114.66(15) . . ?
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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1902446'
loop_
_audit_author_name
_audit_author_address
'Iain D H Oswald '
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2019-04-24 deposited with the CCDC.	2019-05-09 downloaded from the CCDC.
;
#data_mo_pcm_02gg_070119_0m
_audit_creation_date             2019-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'paracetamol:methanol solvate, (1:1)'
_chemical_name_systematic        'acetaminophen:methanol solvate'
_chemical_formula_moiety         'C H4 O, C8 H9 N O2'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0234(15)
_cell_length_b                   17.2078(9)
_cell_length_c                   13.0925(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.209(7)
_cell_angle_gamma                90
_cell_volume                     2632.4(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.12
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1071 before and 0.0616 after correction. The Ratio of minimum to maximum transmission is 0.8490. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'crystallization occurred at 0.72 GPa during decompression from approx 0.8 GPa'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.320
_diffrn_reflns_Laue_measured_fraction_max 0.320
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12022
_diffrn_reflns_point_group_measured_fraction_full 0.320
_diffrn_reflns_point_group_measured_fraction_max 0.320
_diffrn_reflns_theta_full        23.294
_diffrn_reflns_theta_max         23.294
_diffrn_reflns_theta_min         2.935
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.320
_diffrn_measured_fraction_theta_max 0.320
_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          'high pressure dataset, diamond anvil cell'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                819
_reflns_number_total             1214
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker, Apex3'
_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)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0941
_refine_ls_restrained_S_all      1.065
_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)+(0.1537P)²+6.2874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2449
_refine_ls_wR_factor_ref         0.2721
_refine_special_details          'RIGU applied'
_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:
 N1C(H1CA), N1A(H1AA), N1B(H1BA), C5A(H5A), C6A(H6A), C2A(H2A), C3A(H3A),
 C2C(H2C), C3C(H3C), C5C(H5C), C6C(H6C), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B)
3.b Fitted hexagon refined as free rotating group:
 C4A(C5A,C6A,C1A,C2A,C3A), C1C(C2C,C3C,C4C,C5C,C6C), C1B(C2B,C3B,C4B,C5B,C6B)
3.c Tetrahedral OH refined with riding coordinates:
 O3C(H3CA), O3A(H3AA), O3B(H3BA)
3.d Idealised Me refined as rotating group:
 C9C(H9CA,H9CB,H9CC), C8C(H8CA,H8CB,H8CC), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,
 H8AC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
3.e Idealised tetrahedral OH refined as rotating group:
 O1C(H1C), O1B(H1B), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3C O 1.2529(9) 0.4156(3) 0.8526(7) 0.0290(17) Uiso 1 1 d . U . . .
H3CA H 1.2526 0.4498 0.8089 0.044 Uiso 1 1 calc R . . . .
O2C O 0.7762(8) 0.4752(3) 0.3075(7) 0.0264(16) Uiso 1 1 d . U . . .
O1C O 1.1225(8) 0.2937(3) 0.7730(7) 0.0252(16) Uiso 1 1 d . U . . .
H1C H 1.1403 0.3295 0.8190 0.038 Uiso 1 1 calc GR . . . .
O1B O 0.5160(8) 0.3008(3) 0.5128(6) 0.0241(16) Uiso 1 1 d . U . . .
H1B H 0.5623 0.3366 0.5324 0.036 Uiso 1 1 calc GR . . . .
O2B O 0.1595(8) 0.4742(3) 0.0464(7) 0.0248(16) Uiso 1 1 d . U . . .
O2A O 0.6255(8) 0.5288(3) 0.4236(7) 0.0285(16) Uiso 1 1 d . U . . .
O3A O 0.1198(10) 0.5973(3) -0.0972(8) 0.043(2) Uiso 1 1 d . U . . .
H3AA H 0.1223 0.5581 -0.0605 0.065 Uiso 1 1 calc R . . . .
O1A O 0.2833(8) 0.6990(3) -0.0501(7) 0.0301(17) Uiso 1 1 d . U . . .
H1A H 0.2690 0.6610 -0.0921 0.045 Uiso 1 1 calc GR . . . .
O3B O 0.6558(9) 0.4192(3) 0.5829(7) 0.0326(18) Uiso 1 1 d . U . . .
H3BA H 0.6548 0.4532 0.5385 0.049 Uiso 1 1 calc R . . . .
N1C N 0.7415(10) 0.3590(4) 0.3643(8) 0.0189(18) Uiso 1 1 d . U . . .
H1CA H 0.6915 0.3223 0.3447 0.023 Uiso 1 1 calc R . . . .
N1A N 0.6601(10) 0.6448(4) 0.3666(8) 0.0227(18) Uiso 1 1 d . U . . .
H1AA H 0.7104 0.6812 0.3855 0.027 Uiso 1 1 calc R . . . .
C9C C 1.3525(13) 0.4224(6) 0.9567(10) 0.030(2) Uiso 1 1 d . U . . .
H9CA H 1.4183 0.4265 0.9420 0.045 Uiso 1 1 calc GR . . . .
H9CB H 1.3599 0.3774 1.0027 0.045 Uiso 1 1 calc GR . . . .
H9CC H 1.3470 0.4681 0.9961 0.045 Uiso 1 1 calc GR . . . .
N1B N 0.1474(10) 0.3496(4) 0.0890(8) 0.0214(18) Uiso 1 1 d . U . . .
H1BA H 0.1082 0.3077 0.0635 0.026 Uiso 1 1 calc R . . . .
C8C C 0.6000(13) 0.4127(6) 0.1902(10) 0.029(2) Uiso 1 1 d . U . . .
H8CA H 0.6079 0.4119 0.1207 0.044 Uiso 1 1 calc GR . . . .
H8CB H 0.5540 0.4563 0.1897 0.044 Uiso 1 1 calc GR . . . .
H8CC H 0.5639 0.3655 0.1966 0.044 Uiso 1 1 calc GR . . . .
C9A C 0.0296(17) 0.5902(5) -0.2087(12) 0.042(3) Uiso 1 1 d . U . . .
H9AA H 0.0565 0.5626 -0.2559 0.063 Uiso 1 1 calc GR . . . .
H9AB H 0.0041 0.6410 -0.2398 0.063 Uiso 1 1 calc GR . . . .
H9AC H -0.0328 0.5622 -0.2058 0.063 Uiso 1 1 calc GR . . . .
C7C C 0.7170(13) 0.4193(5) 0.2902(10) 0.021(2) Uiso 1 1 d . U . . .
C8A C 0.7978(13) 0.5916(6) 0.5441(11) 0.028(2) Uiso 1 1 d . U . . .
H8AA H 0.7873 0.5824 0.6112 0.042 Uiso 1 1 calc GR . . . .
H8AB H 0.8280 0.6430 0.5473 0.042 Uiso 1 1 calc GR . . . .
H8AC H 0.8503 0.5541 0.5399 0.042 Uiso 1 1 calc GR . . . .
C7A C 0.6849(13) 0.5846(5) 0.4408(10) 0.026(2) Uiso 1 1 d . U . . .
C4A C 0.3742(6) 0.6824(3) 0.0529(5) 0.022(2) Uiso 1 1 d . U . . .
C5A C 0.4721(7) 0.7276(3) 0.0868(5) 0.031(3) Uiso 1 1 d G U . . .
H5A H 0.4752 0.7671 0.0397 0.038 Uiso 1 1 calc R . . . .
C6A C 0.5655(6) 0.7139(3) 0.1911(6) 0.028(2) Uiso 1 1 d G U . . .
H6A H 0.6310 0.7442 0.2138 0.034 Uiso 1 1 calc R . . . .
C1A C 0.5608(6) 0.6550(3) 0.2615(5) 0.022(2) Uiso 1 1 d G U . . .
C2A C 0.4629(7) 0.6097(3) 0.2276(5) 0.026(2) Uiso 1 1 d G U . . .
H2A H 0.4598 0.5702 0.2747 0.032 Uiso 1 1 calc R . . . .
C3A C 0.3695(6) 0.6234(3) 0.1233(6) 0.022(2) Uiso 1 1 d G U . . .
H3A H 0.3040 0.5931 0.1006 0.026 Uiso 1 1 calc R . . . .
C1C C 0.8397(6) 0.3490(3) 0.4705(5) 0.018(2) Uiso 1 1 d . U . . .
C2C C 0.9365(7) 0.3957(3) 0.5081(5) 0.022(2) Uiso 1 1 d G U . . .
H2C H 0.9380 0.4383 0.4650 0.026 Uiso 1 1 calc R . . . .
C3C C 1.0312(6) 0.3788(3) 0.6100(6) 0.020(2) Uiso 1 1 d G U . . .
H3C H 1.0960 0.4101 0.6352 0.024 Uiso 1 1 calc R . . . .
C4C C 1.0290(6) 0.3152(3) 0.6743(5) 0.017(2) Uiso 1 1 d G U . . .
C5C C 0.9321(6) 0.2684(3) 0.6367(5) 0.023(2) Uiso 1 1 d G U . . .
H5C H 0.9307 0.2258 0.6798 0.028 Uiso 1 1 calc R . . . .
C6C C 0.8375(6) 0.2853(3) 0.5348(6) 0.024(2) Uiso 1 1 d G U . . .
H6C H 0.7727 0.2540 0.5096 0.029 Uiso 1 1 calc R . . . .
C7B C 0.1120(13) 0.4109(5) 0.0184(11) 0.025(2) Uiso 1 1 d . U . . .
C1B C 0.2398(7) 0.3436(3) 0.1992(5) 0.018(2) Uiso 1 1 d . U . . .
C2B C 0.3321(7) 0.3945(3) 0.2382(5) 0.023(2) Uiso 1 1 d G U . . .
H2B H 0.3316 0.4371 0.1942 0.028 Uiso 1 1 calc R . . . .
C3B C 0.4253(6) 0.3817(3) 0.3430(6) 0.022(2) Uiso 1 1 d G U . . .
H3B H 0.4871 0.4158 0.3691 0.026 Uiso 1 1 calc R . . . .
C4B C 0.4262(7) 0.3181(3) 0.4087(6) 0.021(2) Uiso 1 1 d G U . . .
C5B C 0.3338(7) 0.2672(3) 0.3697(5) 0.026(2) Uiso 1 1 d G U . . .
H5B H 0.3344 0.2246 0.4137 0.032 Uiso 1 1 calc R . . . .
C6B C 0.2406(6) 0.2799(3) 0.2649(6) 0.022(2) Uiso 1 1 d G U . . .
H6B H 0.1788 0.2459 0.2388 0.026 Uiso 1 1 calc R . . . .
C8B C 0.0088(12) 0.3998(6) -0.0904(10) 0.028(2) Uiso 1 1 d . U . . .
H8BA H 0.0306 0.3960 -0.1513 0.042 Uiso 1 1 calc GR . . . .
H8BB H -0.0418 0.4433 -0.1037 0.042 Uiso 1 1 calc GR . . . .
H8BC H -0.0295 0.3530 -0.0868 0.042 Uiso 1 1 calc GR . . . .
C9B C 0.7596(13) 0.4230(6) 0.6825(10) 0.031(2) Uiso 1 1 d . U . . .
H9BA H 0.8222 0.4244 0.6626 0.046 Uiso 1 1 calc GR . . . .
H9BB H 0.7667 0.3780 0.7286 0.046 Uiso 1 1 calc GR . . . .
H9BC H 0.7607 0.4690 0.7243 0.046 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
O3C H3CA 0.8200 . ?
O3C C9C 1.411(8) . ?
O2C C7C 1.190(14) . ?
O1C H1C 0.8200 . ?
O1C C4C 1.378(5) . ?
O1B H1B 0.8200 . ?
O1B C4B 1.381(5) . ?
O2B C7B 1.226(10) . ?
O2A C7A 1.191(14) . ?
O3A H3AA 0.8200 . ?
O3A C9A 1.418(9) . ?
O1A H1A 0.8200 . ?
O1A C4A 1.375(5) . ?
O3B H3BA 0.8200 . ?
O3B C9B 1.405(9) . ?
N1C H1CA 0.8600 . ?
N1C C7C 1.360(13) . ?
N1C C1C 1.423(6) . ?
N1A H1AA 0.8600 . ?
N1A C7A 1.358(13) . ?
N1A C1A 1.422(6) . ?
C9C H9CA 0.9600 . ?
C9C H9CB 0.9600 . ?
C9C H9CC 0.9600 . ?
N1B H1BA 0.8600 . ?
N1B C7B 1.344(11) . ?
N1B C1B 1.416(6) . ?
C8C H8CA 0.9600 . ?
C8C H8CB 0.9600 . ?
C8C H8CC 0.9600 . ?
C8C C7C 1.513(12) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C8A C7A 1.500(11) . ?
C4A C5A 1.3900 . ?
C4A C3A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C1A 1.3900 . ?
C1A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9300 . ?
C1C C2C 1.3900 . ?
C1C C6C 1.3900 . ?
C2C H2C 0.9300 . ?
C2C C3C 1.3900 . ?
C3C H3C 0.9300 . ?
C3C C4C 1.3900 . ?
C4C C5C 1.3900 . ?
C5C H5C 0.9300 . ?
C5C C6C 1.3900 . ?
C6C H6C 0.9300 . ?
C7B C8B 1.477(10) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C2B H2B 0.9300 . ?
C2B C3B 1.3900 . ?
C3B H3B 0.9300 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C5B H5B 0.9300 . ?
C5B C6B 1.3900 . ?
C6B H6B 0.9300 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?

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
C9C O3C H3CA 109.5 . . ?
C4C O1C H1C 109.5 . . ?
C4B O1B H1B 109.5 . . ?
C9A O3A H3AA 109.5 . . ?
C4A O1A H1A 109.5 . . ?
C9B O3B H3BA 109.5 . . ?
C7C N1C H1CA 116.0 . . ?
C7C N1C C1C 128.0(8) . . ?
C1C N1C H1CA 116.0 . . ?
C7A N1A H1AA 116.1 . . ?
C7A N1A C1A 127.8(9) . . ?
C1A N1A H1AA 116.1 . . ?
O3C C9C H9CA 109.5 . . ?
O3C C9C H9CB 109.5 . . ?
O3C C9C H9CC 109.5 . . ?
H9CA C9C H9CB 109.5 . . ?
H9CA C9C H9CC 109.5 . . ?
H9CB C9C H9CC 109.5 . . ?
C7B N1B H1BA 115.2 . . ?
C7B N1B C1B 129.5(7) . . ?
C1B N1B H1BA 115.2 . . ?
H8CA C8C H8CB 109.5 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
C7C C8C H8CA 109.5 . . ?
C7C C8C H8CB 109.5 . . ?
C7C C8C H8CC 109.5 . . ?
O3A C9A H9AA 109.5 . . ?
O3A C9A H9AB 109.5 . . ?
O3A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O2C C7C N1C 123.6(7) . . ?
O2C C7C C8C 123.1(8) . . ?
N1C C7C C8C 112.9(11) . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
O2A C7A N1A 123.5(7) . . ?
O2A C7A C8A 122.1(9) . . ?
N1A C7A C8A 114.4(11) . . ?
O1A C4A C5A 117.9(6) . . ?
O1A C4A C3A 122.1(6) . . ?
C5A C4A C3A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A C5A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C6A C1A N1A 116.4(7) . . ?
C6A C1A C2A 120.0 . . ?
C2A C1A N1A 123.6(7) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C2C C1C N1C 124.0(6) . . ?
C2C C1C C6C 120.0 . . ?
C6C C1C N1C 115.9(6) . . ?
C1C C2C H2C 120.0 . . ?
C1C C2C C3C 120.0 . . ?
C3C C2C H2C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C4C C3C C2C 120.0 . . ?
C4C C3C H3C 120.0 . . ?
O1C C4C C3C 122.2(6) . . ?
O1C C4C C5C 117.7(5) . . ?
C5C C4C C3C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C4C C5C C6C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C1C C6C H6C 120.0 . . ?
C5C C6C C1C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
O2B C7B N1B 121.2(7) . . ?
O2B C7B C8B 121.8(8) . . ?
N1B C7B C8B 116.8(9) . . ?
C2B C1B N1B 122.4(6) . . ?
C2B C1B C6B 120.0 . . ?
C6B C1B N1B 117.3(6) . . ?
C1B C2B H2B 120.0 . . ?
C1B C2B C3B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
O1B C4B C3B 123.5(5) . . ?
O1B C4B C5B 116.5(5) . . ?
C5B C4B C3B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O3B C9B H9BA 109.5 . . ?
O3B C9B H9BB 109.5 . . ?
O3B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'Diamond anvil cell'
_olex2_submission_special_instructions 'No special instructions were received'
