#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:32:41 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180399 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/68/7206871.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_7206871
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_absolute_configuration ad
_chemical_formula_moiety         'C18 H12 Br2 O7'
_chemical_formula_sum            'C18 H12 Br2 O7'
_chemical_formula_weight         500.10
_chemical_name_common            '5-Br-aspirin anhydride (form I)'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5579(5)
_cell_length_b                   12.5176(7)
_cell_length_c                   13.7487(8)
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.43
_cell_volume                     1817.02(17)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17330
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         3.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.500
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack (1983), 1464 Friedel pairs'
_refine_ls_abs_structure_Flack   0.005(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0181
_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)+(0.0131P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0391
_reflns_number_gt                3211
_reflns_number_total             3427
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c1ce06065a.txt
_cod_data_source_block           5-Br-AA_I
_cod_database_code               7206871
loop_
_symmetry_equiv_pos_as_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'
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
Br1 Br 0.16973(2) 0.61534(2) 0.209946(18) 0.03024(7) Uani 1 1 d .
Br2 Br 0.85501(2) 0.340269(19) 0.072010(17) 0.03107(7) Uani 1 1 d .
O1 O 0.65815(14) 0.66928(12) 0.24662(11) 0.0240(3) Uani 1 1 d .
O2 O 0.72563(15) 0.82205(14) 0.17935(13) 0.0410(5) Uani 1 1 d .
O3 O 0.57045(13) 0.89910(12) 0.03400(10) 0.0219(3) Uani 1 1 d .
O4 O 0.52801(18) 1.02668(14) 0.14339(14) 0.0460(5) Uani 1 1 d .
O5 O 0.77902(15) 0.72947(12) 0.37042(11) 0.0281(4) Uani 1 1 d .
O6 O 0.95961(13) 0.58942(11) 0.43913(11) 0.0215(3) Uani 1 1 d .
O7 O 0.90576(15) 0.45447(13) 0.53904(11) 0.0285(4) Uani 1 1 d .
C1 C 0.5114(2) 0.76502(16) 0.15268(16) 0.0175(5) Uani 1 1 d .
C2 C 0.47841(19) 0.83553(17) 0.07823(15) 0.0194(5) Uani 1 1 d .
C3 C 0.3564(2) 0.84026(18) 0.04316(15) 0.0237(5) Uani 1 1 d .
H3A H 0.3363 0.8885 -0.0079 0.028 Uiso 1 1 calc R
C4 C 0.2628(2) 0.77543(17) 0.08154(16) 0.0240(5) Uani 1 1 d .
H4A H 0.1783 0.7790 0.0580 0.029 Uiso 1 1 calc R
C5 C 0.2953(2) 0.70538(18) 0.15490(16) 0.0213(5) Uani 1 1 d .
C6 C 0.41676(19) 0.69823(17) 0.19068(15) 0.0186(5) Uani 1 1 d .
H6A H 0.4364 0.6485 0.2407 0.022 Uiso 1 1 calc R
C7 C 0.6414(2) 0.75966(17) 0.19232(15) 0.0216(5) Uani 1 1 d .
C8 C 0.5894(2) 0.99685(19) 0.07591(19) 0.0285(5) Uani 1 1 d .
C9 C 0.6914(2) 1.0559(2) 0.02434(19) 0.0364(7) Uani 1 1 d .
H9A H 0.7412 1.0968 0.0715 0.055 Uiso 1 1 calc R
H9B H 0.6536 1.1047 -0.0232 0.055 Uiso 1 1 calc R
H9C H 0.7466 1.0049 -0.0093 0.055 Uiso 1 1 calc R
C10 C 0.76058(19) 0.66226(18) 0.31129(15) 0.0196(5) Uani 1 1 d .
C11 C 0.83363(19) 0.56250(15) 0.29479(15) 0.0166(4) Uani 1 1 d .
C12 C 0.81152(19) 0.50326(17) 0.21042(16) 0.0197(5) Uani 1 1 d .
H12A H 0.7460 0.5241 0.1671 0.024 Uiso 1 1 calc R
C13 C 0.8842(2) 0.41483(16) 0.18972(15) 0.0205(5) Uani 1 1 d .
C14 C 0.9799(2) 0.38212(18) 0.25158(16) 0.0224(5) Uani 1 1 d .
H14A H 1.0306 0.3217 0.2362 0.027 Uiso 1 1 calc R
C15 C 1.0002(2) 0.43929(18) 0.33638(17) 0.0221(5) Uani 1 1 d .
H15A H 1.0642 0.4167 0.3804 0.027 Uiso 1 1 calc R
C16 C 0.9290(2) 0.52857(17) 0.35797(15) 0.0180(5) Uani 1 1 d .
C17 C 0.9486(2) 0.54217(19) 0.52854(16) 0.0215(5) Uani 1 1 d .
C18 C 0.9948(2) 0.6153(2) 0.60660(16) 0.0307(6) Uani 1 1 d .
H18A H 0.9794 0.5826 0.6703 0.046 Uiso 1 1 calc R
H18B H 0.9495 0.6834 0.6025 0.046 Uiso 1 1 calc R
H18C H 1.0858 0.6277 0.5982 0.046 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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 C10 119.86(17)
C8 O3 C2 115.37(17)
C17 O6 C16 117.69(16)
C2 C1 C6 118.1(2)
C2 C1 C7 122.07(19)
C6 C1 C7 119.78(19)
C3 C2 O3 118.33(19)
C3 C2 C1 121.2(2)
O3 C2 C1 120.41(19)
C2 C3 C4 120.6(2)
C2 C3 H3A 119.7
C4 C3 H3A 119.7
C5 C4 C3 118.3(2)
C5 C4 H4A 120.8
C3 C4 H4A 120.8
C6 C5 C4 122.3(2)
C6 C5 Br1 118.02(17)
C4 C5 Br1 119.67(17)
C5 C6 C1 119.4(2)
C5 C6 H6A 120.3
C1 C6 H6A 120.3
O2 C7 O1 121.7(2)
O2 C7 C1 127.3(2)
O1 C7 C1 111.05(18)
O4 C8 O3 122.0(2)
O4 C8 C9 127.6(2)
O3 C8 C9 110.5(2)
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
O5 C10 O1 121.1(2)
O5 C10 C11 128.0(2)
O1 C10 C11 110.87(18)
C16 C11 C12 118.41(18)
C16 C11 C10 122.37(19)
C12 C11 C10 119.12(19)
C13 C12 C11 120.4(2)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C12 C13 C14 121.2(2)
C12 C13 Br2 118.83(16)
C14 C13 Br2 119.91(17)
C13 C14 C15 118.6(2)
C13 C14 H14A 120.7
C15 C14 H14A 120.7
C16 C15 C14 121.0(2)
C16 C15 H15A 119.5
C14 C15 H15A 119.5
C15 C16 O6 119.39(19)
C15 C16 C11 120.4(2)
O6 C16 C11 120.04(18)
O7 C17 O6 122.5(2)
O7 C17 C18 126.8(2)
O6 C17 C18 110.7(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.898(2)
Br2 C13 1.894(2)
O1 C7 1.367(2)
O1 C10 1.403(2)
O2 C7 1.197(3)
O3 C8 1.367(3)
O3 C2 1.395(2)
O4 C8 1.191(3)
O5 C10 1.186(2)
O6 C17 1.369(3)
O6 C16 1.389(3)
O7 C17 1.196(3)
C1 C2 1.396(3)
C1 C6 1.404(3)
C1 C7 1.478(3)
C2 C3 1.377(3)
C3 C4 1.383(3)
C3 H3A 0.950
C4 C5 1.380(3)
C4 H4A 0.950
C5 C6 1.376(3)
C6 H6A 0.950
C8 C9 1.486(3)
C9 H9A 0.980
C9 H9B 0.980
C9 H9C 0.980
C10 C11 1.485(3)
C11 C16 1.396(3)
C11 C12 1.396(3)
C12 C13 1.377(3)
C12 H12A 0.950
C13 C14 1.383(3)
C14 C15 1.385(3)
C14 H14A 0.950
C15 C16 1.379(3)
C15 H15A 0.950
C17 C18 1.492(3)
C18 H18A 0.980
C18 H18B 0.980
C18 H18C 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 93.0(2)
C8 O3 C2 C1 -90.3(2)
C6 C1 C2 C3 0.4(3)
C7 C1 C2 C3 -179.1(2)
C6 C1 C2 O3 -176.19(18)
C7 C1 C2 O3 4.3(3)
O3 C2 C3 C4 177.12(19)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 -0.7(3)
C3 C4 C5 C6 0.1(3)
C3 C4 C5 Br1 179.77(16)
C4 C5 C6 C1 0.8(3)
Br1 C5 C6 C1 -178.91(15)
C2 C1 C6 C5 -1.0(3)
C7 C1 C6 C5 178.5(2)
C10 O1 C7 O2 18.7(3)
C10 O1 C7 C1 -162.87(18)
C2 C1 C7 O2 12.8(4)
C6 C1 C7 O2 -166.7(2)
C2 C1 C7 O1 -165.44(18)
C6 C1 C7 O1 15.0(3)
C2 O3 C8 O4 -2.5(3)
C2 O3 C8 C9 178.54(18)
C7 O1 C10 O5 52.8(3)
C7 O1 C10 C11 -128.32(18)
O5 C10 C11 C16 8.1(3)
O1 C10 C11 C16 -170.70(18)
O5 C10 C11 C12 -168.3(2)
O1 C10 C11 C12 13.0(3)
C16 C11 C12 C13 -1.2(3)
C10 C11 C12 C13 175.22(19)
C11 C12 C13 C14 0.3(3)
C11 C12 C13 Br2 -177.60(15)
C12 C13 C14 C15 1.1(3)
Br2 C13 C14 C15 178.99(16)
C13 C14 C15 C16 -1.6(3)
C14 C15 C16 O6 -174.20(19)
C14 C15 C16 C11 0.7(3)
C17 O6 C16 C15 -64.0(3)
C17 O6 C16 C11 121.1(2)
C12 C11 C16 C15 0.7(3)
C10 C11 C16 C15 -175.61(19)
C12 C11 C16 O6 175.59(18)
C10 C11 C16 O6 -0.7(3)
C16 O6 C17 O7 -5.4(3)
C16 O6 C17 C18 175.44(18)
