#------------------------------------------------------------------------------
#$Date: 2023-12-04 20:14:58 +0200 (Mon, 04 Dec 2023) $
#$Revision: 288016 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247819.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_7247819
loop_
_publ_author_name
'Muthusamy, Ramya'
'Karuppannan, Srinivasan'
_publ_section_title
;
 Liquid--liquid phase separation and crystallization of aspirin polymorphs
 from a water--acetonitrile mixed solvent medium through a swift cooling
 process
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              6611
_journal_page_last               6621
_journal_paper_doi               10.1039/D3CE00611E
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C9 H8 04'
_chemical_formula_sum            'C9 H8 O4'
_chemical_formula_weight         180.15
_chemical_name_common            'Acetylsalicylic acid'
_chemical_name_systematic        2-acetoxybenzoicacid
_chemical_properties_physical    Hygroscopic
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2bnj5q
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-04-06 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.750(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.429(4)
_cell_length_b                   6.597(2)
_cell_length_c                   11.395(4)
_cell_measurement_reflns_used    6570
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.47
_cell_measurement_theta_min      3.57
_cell_volume                     854.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and Encifer'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-III CMOS Photon Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45382
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_min         3.570
_diffrn_source                   'Sealed Microfocus Tube'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'B.H.Blessings,Acta CrystalograA,1995,51,33'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method 'Solution-state crystallization method'
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.9970
_exptl_transmission_factor_min   0.9500
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0524
_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)+(0.0494P)²+0.2533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1141
_reflns_number_total             1946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00611e2.cif
_cod_data_source_block           ASAMONOP_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        854.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247819
_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_min   0.950
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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_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
O3 O 0.21473(12) 0.4113(2) 0.58794(11) 0.0410(4) Uani 1 1 d . . . . .
O1 O 0.37983(13) 0.1402(2) 0.55085(14) 0.0513(5) Uani 1 1 d . . . . .
H1 H 0.424304 0.043231 0.563006 0.077 Uiso 1 1 calc R U . . .
O2 O 0.48955(14) 0.1880(2) 0.40343(13) 0.0528(5) Uani 1 1 d . . . . .
O4 O 0.09651(15) 0.2205(3) 0.46551(13) 0.0614(5) Uani 1 1 d . . . . .
C7 C 0.40975(17) 0.2429(3) 0.46213(16) 0.0355(5) Uani 1 1 d . . . . .
C1 C 0.34702(17) 0.4357(3) 0.43238(17) 0.0349(5) Uani 1 1 d . . . . .
C2 C 0.25423(18) 0.5122(3) 0.49045(16) 0.0369(5) Uani 1 1 d . . . . .
C6 C 0.38307(18) 0.5501(3) 0.34026(18) 0.0414(5) Uani 1 1 d . . . . .
H6 H 0.444634 0.503086 0.300116 0.050 Uiso 1 1 calc R U . . .
C8 C 0.13424(19) 0.2617(3) 0.56368(18) 0.0411(5) Uani 1 1 d . . . . .
C3 C 0.20213(19) 0.6940(3) 0.4584(2) 0.0473(6) Uani 1 1 d . . . . .
H3 H 0.141326 0.743686 0.498672 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3300(2) 0.7312(3) 0.3068(2) 0.0486(6) Uani 1 1 d . . . . .
H5 H 0.354860 0.804659 0.244240 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2402(2) 0.8023(4) 0.3665(2) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.204655 0.925207 0.344605 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1029(2) 0.1634(4) 0.6731(2) 0.0603(7) Uani 1 1 d . . . . .
H9A H 0.047722 0.056069 0.653217 0.090 Uiso 1 1 calc R U . . .
H9B H 0.068252 0.261654 0.721164 0.090 Uiso 1 1 calc R U . . .
H9C H 0.172495 0.108610 0.715717 0.090 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C2 116.55(15) . . ?
C7 O1 H1 109.5 . . ?
O2 C7 O1 122.44(19) . . ?
O2 C7 C1 119.55(18) . . ?
O1 C7 C1 118.00(17) . . ?
C6 C1 C2 117.27(19) . . ?
C6 C1 C7 117.75(17) . . ?
C2 C1 C7 124.98(18) . . ?
C3 C2 C1 121.23(19) . . ?
C3 C2 O3 117.27(18) . . ?
C1 C2 O3 121.41(18) . . ?
C5 C6 C1 121.66(19) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O4 C8 O3 122.11(19) . . ?
O4 C8 C9 126.6(2) . . ?
O3 C8 C9 111.27(18) . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
O3 C8 1.359(3) . ?
O3 C2 1.408(2) . ?
O1 C7 1.292(2) . ?
O1 H1 0.8200 . ?
O2 C7 1.238(2) . ?
O4 C8 1.189(2) . ?
C7 C1 1.483(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.399(3) . ?
C2 C3 1.372(3) . ?
C6 C5 1.377(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.480(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.369(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C1 C6 -1.5(3) . . . . ?
O1 C7 C1 C6 177.19(19) . . . . ?
O2 C7 C1 C2 178.78(19) . . . . ?
O1 C7 C1 C2 -2.5(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C1 C2 C3 178.96(19) . . . . ?
C6 C1 C2 O3 -177.37(17) . . . . ?
C7 C1 C2 O3 2.4(3) . . . . ?
C8 O3 C2 C3 97.9(2) . . . . ?
C8 O3 C2 C1 -85.4(2) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 -179.85(19) . . . . ?
C2 O3 C8 O4 -1.8(3) . . . . ?
C2 O3 C8 C9 178.11(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
O3 C2 C3 C4 177.7(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
