#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/75/7207516.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_7207516
loop_
_publ_author_name
'Perumalla, Sathyanarayana Reddy'
'Shi, Limin'
'Sun, Changquan Calvin'
_publ_section_title
;
 Ionized form of acetaminophen with improved compaction properties
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2389
_journal_paper_doi               10.1039/c1ce06278f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C8 H12 Cl N O3'
_chemical_formula_weight         205.64
_chemical_name_common            'Acetaminophen hydrochloride hydrate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2761(6)
_cell_length_b                   22.345(2)
_cell_length_c                   6.8833(7)
_cell_measurement_reflns_used    5012
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.12
_cell_volume                     957.58(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Apex II platform CCD'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10318
_diffrn_reflns_theta_full        26.84
_diffrn_reflns_theta_max         26.84
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.9426
_exptl_absorpt_correction_T_min  0.8772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.2988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                1853
_reflns_number_total             2043
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06278f.txt
_cod_data_source_block           11048_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        957.56(16)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7207516
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl 0.39914(5) 0.320966(13) 0.53254(5) 0.03390(12) Uani 1 1 d
O4 O 1.14861(18) -0.14149(4) 0.77012(16) 0.0357(2) Uani 1 1 d
O7 O 0.67269(15) 0.11502(4) 0.63529(14) 0.0304(2) Uani 1 1 d
O100 O 0.37965(17) 0.18330(5) 0.48849(18) 0.0363(2) Uani 1 1 d
C2 C 0.8720(2) 0.00176(6) 0.72010(18) 0.0276(3) Uani 1 1 d
N1 N 1.01647(18) 0.10527(4) 0.76777(15) 0.0266(2) Uani 1 1 d
C4 C 1.1207(2) -0.08079(5) 0.76756(17) 0.0270(3) Uani 1 1 d
C1 C 1.0410(2) 0.04170(5) 0.76175(16) 0.0241(2) Uani 1 1 d
C3 C 0.9136(2) -0.05918(6) 0.72274(19) 0.0295(3) Uani 1 1 d
C6 C 1.2499(2) 0.02027(6) 0.80230(18) 0.0289(3) Uani 1 1 d
C8 C 0.8737(3) 0.20524(6) 0.7241(2) 0.0352(3) Uani 1 1 d
C7 C 0.8519(2) 0.13910(5) 0.70803(17) 0.0261(3) Uani 1 1 d
C5 C 1.2903(2) -0.04070(6) 0.80556(19) 0.0292(3) Uani 1 1 d
H5 H 1.433(3) -0.0540(7) 0.833(2) 0.040(4) Uiso 1 1 d
H2 H 0.727(3) 0.0154(7) 0.691(2) 0.040(4) Uiso 1 1 d
H1 H 1.124(3) 0.1233(7) 0.822(2) 0.036(4) Uiso 1 1 d
H6 H 1.367(2) 0.0488(7) 0.832(2) 0.032(4) Uiso 1 1 d
H8C H 0.756(3) 0.2215(9) 0.782(3) 0.060(5) Uiso 1 1 d
H7 H 0.573(3) 0.1415(9) 0.588(3) 0.060(6) Uiso 1 1 d
H4 H 1.265(3) -0.1469(9) 0.820(3) 0.056(6) Uiso 1 1 d
H3 H 0.808(3) -0.0869(8) 0.695(2) 0.039(4) Uiso 1 1 d
H8B H 1.012(3) 0.2166(8) 0.802(3) 0.055(5) Uiso 1 1 d
H10B H 0.388(3) 0.2192(11) 0.516(3) 0.055(6) Uiso 1 1 d
H10A H 0.374(4) 0.1835(9) 0.364(4) 0.065(6) Uiso 1 1 d
H8A H 0.864(3) 0.2217(10) 0.601(3) 0.073(6) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0388(2) 0.02285(17) 0.0377(2) -0.00069(11) -0.00431(14) 0.00220(12)
O4 0.0379(6) 0.0204(5) 0.0483(6) -0.0004(4) 0.0032(5) 0.0025(4)
O7 0.0321(5) 0.0223(4) 0.0357(5) -0.0013(4) -0.0006(4) 0.0014(4)
O100 0.0431(6) 0.0232(5) 0.0396(6) -0.0029(4) -0.0065(5) 0.0017(4)
C2 0.0281(6) 0.0252(6) 0.0295(6) 0.0004(5) 0.0038(5) 0.0001(5)
N1 0.0301(6) 0.0208(5) 0.0279(5) -0.0022(4) -0.0002(4) -0.0028(4)
C4 0.0356(7) 0.0214(6) 0.0245(6) -0.0005(4) 0.0060(5) 0.0009(5)
C1 0.0317(6) 0.0202(5) 0.0204(5) -0.0012(4) 0.0033(5) 0.0004(5)
C3 0.0301(7) 0.0234(6) 0.0352(7) -0.0009(5) 0.0047(5) -0.0046(5)
C6 0.0295(7) 0.0254(6) 0.0305(6) -0.0026(5) -0.0005(5) -0.0027(5)
C8 0.0420(8) 0.0221(6) 0.0400(8) -0.0007(5) -0.0010(6) 0.0004(5)
C7 0.0338(6) 0.0233(6) 0.0215(5) -0.0008(4) 0.0049(5) -0.0009(5)
C5 0.0290(7) 0.0268(6) 0.0313(6) -0.0018(5) 0.0014(5) 0.0028(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'
Cl Cl 0.1484 0.1585 '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 O4 H4 105.8(16)
C7 O7 H7 113.6(13)
H10B O100 H10A 102.9(18)
C3 C2 C1 119.43(12)
C3 C2 H2 119.2(10)
C1 C2 H2 121.4(10)
C7 N1 C1 130.60(11)
C7 N1 H1 115.2(11)
C1 N1 H1 114.1(11)
O4 C4 C3 117.65(12)
O4 C4 C5 122.86(12)
C3 C4 C5 119.48(12)
C2 C1 C6 119.77(11)
C2 C1 N1 124.21(12)
C6 C1 N1 116.02(11)
C4 C3 C2 121.02(12)
C4 C3 H3 116.5(10)
C2 C3 H3 122.5(11)
C5 C6 C1 120.51(12)
C5 C6 H6 120.6(9)
C1 C6 H6 118.8(9)
C7 C8 H8C 109.9(12)
C7 C8 H8B 111.1(11)
H8C C8 H8B 110.4(16)
C7 C8 H8A 109.5(14)
H8C C8 H8A 105.6(18)
H8B C8 H8A 110.2(17)
O7 C7 N1 119.86(11)
O7 C7 C8 120.75(12)
N1 C7 C8 119.40(12)
C6 C5 C4 119.76(12)
C6 C5 H5 118.9(10)
C4 C5 H5 121.4(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C4 1.3676(15)
O4 H4 0.78(2)
O7 C7 1.2895(15)
O7 H7 0.89(2)
O100 H10B 0.82(2)
O100 H10A 0.85(2)
C2 C3 1.3861(18)
C2 C1 1.3881(18)
C2 H2 0.959(17)
N1 C7 1.3040(17)
N1 C1 1.4298(15)
N1 H1 0.834(17)
C4 C3 1.3843(19)
C4 C5 1.3905(18)
C1 C6 1.3906(18)
C3 H3 0.909(17)
C6 C5 1.3854(18)
C6 H6 0.973(16)
C8 C7 1.4871(18)
C8 H8C 0.95(2)
C8 H8B 1.00(2)
C8 H8A 0.92(2)
C5 H5 0.938(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139196260
