#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/91/2219176.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2219176
loop_
_publ_author_name
'Fu, Xianshu'
'Ye, Zihong'
'Mao, Lifei'
'Shao, Sasa'
_publ_section_title
;
 Methyl 6-bromo-7-methoxy-1,3-benzodioxole-5-carboxylate
;
_journal_coeditor_code           TK2272
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1417
_journal_paper_doi               10.1107/S1600536808019399
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H9 Br O5'
_chemical_formula_moiety         'C10 H9 Br O5'
_chemical_formula_sum            'C10 H9 Br O5'
_chemical_formula_weight         289.08
_chemical_melting_point          357
_chemical_name_systematic
;
Methyl 6-bromo-7-methoxy-1,3-benzodioxole-5-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                105.062(2)
_cell_angle_beta                 91.667(2)
_cell_angle_gamma                113.457(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6933(12)
_cell_length_b                   8.0616(13)
_cell_length_c                   9.7039(15)
_cell_measurement_reflns_used    1718
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.92
_cell_volume                     527.13(14)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2997
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.4
_diffrn_reflns_theta_min         2.2
_exptl_absorpt_coefficient_mu    3.902
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.035
_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)+(0.0596P)²+0.1433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.089
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                1790
_reflns_number_total             2129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2272.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               2219176
_cod_database_fobs_code          2219176
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.35252(5) 1.09757(4) 0.17325(3) 0.05585(16) Uani d . 1
O O1 0.4065(4) 0.7325(4) 0.0679(3) 0.0741(8) Uani d . 1
O O2 0.1696(3) 0.4868(3) 0.1074(2) 0.0508(5) Uani d . 1
O O3 0.1494(4) 0.7239(3) 0.6385(2) 0.0559(6) Uani d . 1
O O4 0.1874(4) 1.0334(3) 0.6889(2) 0.0591(6) Uani d . 1
O O5 0.2912(4) 1.2488(3) 0.4655(2) 0.0627(7) Uani d . 1
C C1 0.2920(4) 0.9669(4) 0.3141(3) 0.0379(6) Uani d . 1
C C2 0.2692(4) 1.0680(4) 0.4491(3) 0.0411(6) Uani d . 1
C C3 0.2222(4) 0.9728(4) 0.5508(3) 0.0393(6) Uani d . 1
C C4 0.1986(4) 0.7872(4) 0.5206(3) 0.0394(6) Uani d . 1
C C5 0.2151(4) 0.6849(4) 0.3893(3) 0.0399(6) Uani d . 1
H H5 0.1945 0.5589 0.3711 0.048 Uiso calc R 1
C C6 0.2645(4) 0.7784(4) 0.2832(3) 0.0362(6) Uani d . 1
C C7 0.2905(4) 0.6697(4) 0.1411(3) 0.0430(6) Uani d . 1
C C8 0.1837(6) 0.3669(5) -0.0273(4) 0.0601(9) Uani d . 1
H H8A 0.1717 0.4182 -0.1041 0.090 Uiso calc R 1
H H8B 0.0831 0.2419 -0.0467 0.090 Uiso calc R 1
H H8C 0.3057 0.3608 -0.0206 0.090 Uiso calc R 1
C C9 0.1525(6) 0.8809(5) 0.7482(3) 0.0559(8) Uani d . 1
H H9A 0.2526 0.9183 0.8279 0.067 Uiso calc R 1
H H9B 0.0307 0.8472 0.7844 0.067 Uiso calc R 1
C C10 0.3163(6) 1.3726(5) 0.6061(4) 0.0565(8) Uani d . 1
H H10A 0.1953 1.3405 0.6412 0.085 Uiso calc R 1
H H10B 0.3653 1.5008 0.6025 0.085 Uiso calc R 1
H H10C 0.4053 1.3601 0.6697 0.085 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0810(3) 0.0505(2) 0.0386(2) 0.02651(18) 0.01453(16) 0.01850(15)
O1 0.0930(19) 0.0607(15) 0.0638(17) 0.0274(14) 0.0469(15) 0.0149(13)
O2 0.0636(13) 0.0423(11) 0.0361(11) 0.0205(10) 0.0119(10) -0.0025(9)
O3 0.0856(16) 0.0481(12) 0.0368(11) 0.0277(12) 0.0195(11) 0.0165(10)
O4 0.0962(18) 0.0519(13) 0.0328(11) 0.0369(13) 0.0203(11) 0.0079(10)
O5 0.111(2) 0.0402(12) 0.0420(12) 0.0379(13) 0.0153(13) 0.0095(10)
C1 0.0412(14) 0.0408(15) 0.0303(13) 0.0155(12) 0.0058(11) 0.0109(11)
C2 0.0475(16) 0.0350(14) 0.0372(15) 0.0179(12) 0.0028(12) 0.0045(12)
C3 0.0452(15) 0.0398(14) 0.0293(13) 0.0189(12) 0.0044(11) 0.0031(11)
C4 0.0432(15) 0.0418(15) 0.0321(14) 0.0166(12) 0.0060(11) 0.0110(12)
C5 0.0465(15) 0.0353(14) 0.0370(15) 0.0181(12) 0.0078(12) 0.0073(11)
C6 0.0384(14) 0.0353(14) 0.0309(13) 0.0152(11) 0.0050(11) 0.0040(11)
C7 0.0495(16) 0.0460(16) 0.0348(15) 0.0239(14) 0.0099(13) 0.0073(13)
C8 0.076(2) 0.058(2) 0.0400(17) 0.0346(18) 0.0086(16) -0.0053(15)
C9 0.076(2) 0.059(2) 0.0340(16) 0.0299(17) 0.0155(15) 0.0121(14)
C10 0.080(2) 0.0455(17) 0.0461(18) 0.0349(17) 0.0083(16) 0.0027(14)
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 O2 C8 115.8(3)
C4 O3 C9 105.9(2)
C3 O4 C9 105.8(2)
C2 O5 C10 119.7(2)
C6 C1 C2 122.1(3)
C6 C1 Br1 121.5(2)
C2 C1 Br1 116.4(2)
O5 C2 C3 126.2(3)
O5 C2 C1 117.2(3)
C3 C2 C1 116.6(2)
C2 C3 O4 129.3(3)
C2 C3 C4 121.1(2)
O4 C3 C4 109.6(2)
C5 C4 O3 126.8(3)
C5 C4 C3 123.3(3)
O3 C4 C3 109.8(2)
C4 C5 C6 117.0(3)
C4 C5 H5 121.5
C6 C5 H5 121.5
C1 C6 C5 119.8(2)
C1 C6 C7 122.8(3)
C5 C6 C7 117.4(2)
O1 C7 O2 123.3(3)
O1 C7 C6 125.9(3)
O2 C7 C6 110.8(2)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 O4 108.6(2)
O3 C9 H9A 110.0
O4 C9 H9A 110.0
O3 C9 H9B 110.0
O4 C9 H9B 110.0
H9A C9 H9B 108.3
O5 C10 H10A 109.5
O5 C10 H10B 109.5
H10A C10 H10B 109.5
O5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.895(3)
O1 C7 1.192(4)
O2 C7 1.336(4)
O2 C8 1.446(4)
O3 C4 1.375(3)
O3 C9 1.418(4)
O4 C3 1.375(3)
O4 C9 1.424(4)
O5 C2 1.363(3)
O5 C10 1.421(4)
C1 C6 1.396(4)
C1 C2 1.408(4)
C2 C3 1.374(4)
C3 C4 1.382(4)
C4 C5 1.366(4)
C5 C6 1.404(4)
C5 H5 0.9300
C6 C7 1.496(4)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 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
C10 O5 C2 C3 16.9(5)
C10 O5 C2 C1 -164.8(3)
C6 C1 C2 O5 -177.1(3)
Br1 C1 C2 O5 0.5(4)
C6 C1 C2 C3 1.3(4)
Br1 C1 C2 C3 179.0(2)
O5 C2 C3 O4 -0.2(5)
C1 C2 C3 O4 -178.5(3)
O5 C2 C3 C4 178.2(3)
C1 C2 C3 C4 -0.1(4)
C9 O4 C3 C2 -177.9(3)
C9 O4 C3 C4 3.6(3)
C9 O3 C4 C5 179.7(3)
C9 O3 C4 C3 -3.0(3)
C2 C3 C4 C5 -1.6(4)
O4 C3 C4 C5 177.0(3)
C2 C3 C4 O3 -179.1(3)
O4 C3 C4 O3 -0.4(3)
O3 C4 C5 C6 179.0(3)
C3 C4 C5 C6 2.0(4)
C2 C1 C6 C5 -0.9(4)
Br1 C1 C6 C5 -178.4(2)
C2 C1 C6 C7 -179.2(3)
Br1 C1 C6 C7 3.3(4)
C4 C5 C6 C1 -0.8(4)
C4 C5 C6 C7 177.6(3)
C8 O2 C7 O1 -1.4(5)
C8 O2 C7 C6 -179.1(2)
C1 C6 C7 O1 34.9(5)
C5 C6 C7 O1 -143.4(3)
C1 C6 C7 O2 -147.4(3)
C5 C6 C7 O2 34.2(4)
C4 O3 C9 O4 5.2(4)
C3 O4 C9 O3 -5.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9441241
