#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:32:41 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180399 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/68/7206867.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_7206867
loop_
_publ_author_name
'Solanko, Katarzyna A.'
'Bond., Andrew D.'
_publ_section_title
;
 Influence of impurities on the crystallisation of 5-X-aspirin and
 5-X-aspirin anhydride polymorphs (X = Cl, Br, Me)
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              6991
_journal_paper_doi               10.1039/c1ce06065a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C9 H7 Cl O4'
_chemical_formula_sum            'C9 H7 Cl O4'
_chemical_formula_weight         214.60
_chemical_name_common            '5-chloro-aspirin (form II)'
_chemical_name_systematic        '2-acetyloxy-5-chlorobenzoic acid'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.445(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0838(4)
_cell_length_b                   17.9622(15)
_cell_length_c                   10.4409(7)
_cell_measurement_reflns_used    5535
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      2.27
_cell_volume                     943.09(13)
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_collection       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL v.6.12 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ 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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12316
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         3.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.5114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                1425
_reflns_number_total             1659
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce06065a.txt
_cod_data_source_block           5-Cl-A
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206867
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
_atom_site_refinement_flags
Cl1 Cl 0.84727(10) 0.41267(3) 1.05692(4) 0.03965(19) Uani 1 1 d .
O1 O 0.1829(2) 0.50428(7) 0.66743(12) 0.0247(3) Uani 1 1 d .
H1 H 0.052(5) 0.5228(14) 0.619(2) 0.050(7) Uiso 1 1 d .
O2 O 0.2415(2) 0.44394(7) 0.48676(11) 0.0245(3) Uani 1 1 d .
O3 O 0.6832(2) 0.36020(7) 0.49567(11) 0.0238(3) Uani 1 1 d .
O4 O 0.3672(3) 0.27380(8) 0.50337(13) 0.0369(4) Uani 1 1 d .
C1 C 0.5359(3) 0.41889(9) 0.68242(17) 0.0202(4) Uani 1 1 d .
C2 C 0.7044(3) 0.37007(10) 0.62909(16) 0.0207(4) Uani 1 1 d .
C3 C 0.9107(3) 0.33444(10) 0.70556(17) 0.0254(4) Uani 1 1 d .
H3A H 1.0226 0.3014 0.6673 0.030 Uiso 1 1 calc R
C4 C 0.9556(4) 0.34664(11) 0.83812(18) 0.0274(4) Uani 1 1 d .
H4A H 1.0965 0.3220 0.8914 0.033 Uiso 1 1 calc R
C5 C 0.7911(4) 0.39544(10) 0.89097(17) 0.0259(4) Uani 1 1 d .
C6 C 0.5830(3) 0.43127(10) 0.81541(17) 0.0239(4) Uani 1 1 d .
H6A H 0.4721 0.4643 0.8543 0.029 Uiso 1 1 calc R
C7 C 0.3083(3) 0.45647(9) 0.60157(17) 0.0199(4) Uani 1 1 d .
C8 C 0.4906(4) 0.31234(10) 0.44034(18) 0.0271(4) Uani 1 1 d .
C9 C 0.4638(5) 0.31621(13) 0.29648(19) 0.0411(5) Uani 1 1 d .
H9A H 0.4212 0.2667 0.2599 0.062 Uiso 1 1 calc R
H9B H 0.6315 0.3335 0.2711 0.062 Uiso 1 1 calc R
H9C H 0.3211 0.3510 0.2639 0.062 Uiso 1 1 calc R
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 0.0456(3) 0.0516(4) 0.0189(3) 0.0012(2) -0.0049(2) 0.0105(2)
O1 0.0260(7) 0.0262(7) 0.0203(6) -0.0005(5) -0.0016(5) 0.0071(5)
O2 0.0246(6) 0.0281(7) 0.0194(7) -0.0013(5) -0.0018(5) 0.0040(5)
O3 0.0244(6) 0.0274(7) 0.0198(6) -0.0003(5) 0.0041(5) -0.0013(5)
O4 0.0476(8) 0.0327(8) 0.0307(7) -0.0035(6) 0.0062(6) -0.0171(7)
C1 0.0192(8) 0.0185(9) 0.0222(9) 0.0025(7) 0.0006(7) -0.0034(7)
C2 0.0207(9) 0.0210(9) 0.0204(9) 0.0009(7) 0.0032(7) -0.0053(7)
C3 0.0215(9) 0.0241(10) 0.0304(10) 0.0020(8) 0.0035(7) 0.0015(7)
C4 0.0229(9) 0.0286(10) 0.0287(10) 0.0069(8) -0.0026(7) 0.0024(7)
C5 0.0286(9) 0.0284(10) 0.0194(9) 0.0026(7) -0.0007(7) -0.0008(8)
C6 0.0245(9) 0.0241(10) 0.0228(9) 0.0010(7) 0.0024(7) 0.0008(7)
C7 0.0199(9) 0.0181(9) 0.0219(9) 0.0023(7) 0.0033(7) -0.0028(7)
C8 0.0325(10) 0.0221(10) 0.0263(10) -0.0047(8) 0.0028(8) 0.0001(8)
C9 0.0530(13) 0.0447(13) 0.0252(11) -0.0074(9) 0.0041(9) -0.0054(10)
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'
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
C7 O1 H1 109.8(16)
C8 O3 C2 116.63(13)
C6 C1 C2 118.17(15)
C6 C1 C7 119.89(15)
C2 C1 C7 121.93(15)
C3 C2 O3 117.42(15)
C3 C2 C1 121.28(16)
O3 C2 C1 121.11(15)
C2 C3 C4 120.29(17)
C2 C3 H3A 119.9
C4 C3 H3A 119.9
C5 C4 C3 118.57(16)
C5 C4 H4A 120.7
C3 C4 H4A 120.7
C4 C5 C6 121.68(17)
C4 C5 Cl1 119.32(14)
C6 C5 Cl1 119.00(14)
C5 C6 C1 120.00(17)
C5 C6 H6A 120.0
C1 C6 H6A 120.0
O2 C7 O1 123.11(15)
O2 C7 C1 123.71(16)
O1 C7 C1 113.17(15)
O4 C8 O3 122.25(17)
O4 C8 C9 127.22(18)
O3 C8 C9 110.53(16)
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
Cl1 C5 1.7419(18)
O1 C7 1.321(2)
O1 H1 0.85(3)
O2 C7 1.218(2)
O3 C8 1.366(2)
O3 C2 1.393(2)
O4 C8 1.195(2)
C1 C6 1.392(2)
C1 C2 1.397(2)
C1 C7 1.490(2)
C2 C3 1.379(2)
C3 C4 1.387(3)
C3 H3A 0.950
C4 C5 1.381(3)
C4 H4A 0.950
C5 C6 1.382(2)
C6 H6A 0.950
C8 C9 1.490(3)
C9 H9A 0.980
C9 H9B 0.980
C9 H9C 0.980
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
C8 O3 C2 C3 103.37(18)
C8 O3 C2 C1 -81.6(2)
C6 C1 C2 C3 0.5(2)
C7 C1 C2 C3 -178.57(16)
C6 C1 C2 O3 -174.29(15)
C7 C1 C2 O3 6.6(2)
O3 C2 C3 C4 174.86(15)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 -0.5(3)
C3 C4 C5 C6 0.8(3)
C3 C4 C5 Cl1 -179.01(14)
C4 C5 C6 C1 -0.4(3)
Cl1 C5 C6 C1 179.40(13)
C2 C1 C6 C5 -0.3(3)
C7 C1 C6 C5 178.85(16)
C6 C1 C7 O2 -173.88(16)
C2 C1 C7 O2 5.2(3)
C6 C1 C7 O1 5.2(2)
C2 C1 C7 O1 -175.71(15)
C2 O3 C8 O4 -8.9(2)
C2 O3 C8 C9 171.33(15)
