#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/26/2212686.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_2212686
loop_
_publ_author_name
'Yathirajan, H. S.'
'Bindya, S.'
'Sarojini, B. K.'
'Narayana, B.'
'Bolte, Michael'
_publ_section_title
;
 Methyl 4-(bromomethyl)benzoate
;
_journal_coeditor_code           SG2133
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1334
_journal_page_last               o1335
_journal_paper_doi               10.1107/S1600536807007258
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H9 Br O2'
_chemical_formula_moiety         'C9 H9 Br O2'
_chemical_formula_sum            'C9 H9 Br O2'
_chemical_formula_weight         229.07
_chemical_name_systematic
;
Methyl 4-(bromomethyl)benzoate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4481(3)
_cell_length_b                   6.1860(3)
_cell_length_c                   33.048(2)
_cell_measurement_reflns_used    11663
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.0
_cell_volume                     909.35(9)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_diffrn_measurement_method       ω
_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  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            13106
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.475
_exptl_absorpt_correction_T_max  0.6157
_exptl_absorpt_correction_T_min  0.4008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.630
_refine_ls_abs_structure_details 'Flack (1983), 837 Friedel pairs'
_refine_ls_abs_structure_Flack   0.002(18)
_refine_ls_extinction_coef       0.053(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0706P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                2052
_reflns_number_total             2164
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2133.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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               2212686
_cod_database_fobs_code          2212686
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_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 0.94932(10) -0.04831(7) 0.023481(12) 0.05488(19) Uani d . 1
O O1 0.2950(7) 0.3564(6) 0.21390(9) 0.0565(7) Uani d . 1
O O2 0.3217(7) 0.6783(5) 0.18298(9) 0.0501(6) Uani d . 1
C C1 0.5786(8) 0.3886(6) 0.15287(11) 0.0426(7) Uani d . 1
C C2 0.6990(9) 0.1799(6) 0.15654(12) 0.0453(8) Uani d . 1
H H2 0.6499 0.0928 0.1793 0.054 Uiso calc R 1
C C3 0.8903(8) 0.1010(6) 0.12677(12) 0.0470(8) Uani d . 1
H H3 0.9733 -0.0398 0.1295 0.056 Uiso calc R 1
C C4 0.9616(9) 0.2241(6) 0.09318(11) 0.0458(7) Uani d . 1
C C5 0.8386(9) 0.4309(6) 0.08949(12) 0.0488(8) Uani d . 1
H H5 0.8837 0.5162 0.0664 0.059 Uiso calc R 1
C C6 0.6510(10) 0.5127(6) 0.11935(12) 0.0477(8) Uani d . 1
H H6 0.5716 0.6546 0.1168 0.057 Uiso calc R 1
C C7 0.3836(8) 0.4694(6) 0.18636(12) 0.0448(7) Uani d . 1
C C8 0.1397(11) 0.7669(7) 0.21558(12) 0.0538(9) Uani d . 1
H H8A -0.0619 0.7033 0.2146 0.081 Uiso calc R 1
H H8B 0.1249 0.9241 0.2125 0.081 Uiso calc R 1
H H8C 0.2336 0.7330 0.2416 0.081 Uiso calc R 1
C C9 1.1710(10) 0.1371(8) 0.06182(14) 0.0567(9) Uani d . 1
H H9A 1.3320 0.0521 0.0750 0.068 Uiso calc R 1
H H9B 1.2660 0.2583 0.0470 0.068 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 0.0687(3) 0.0494(3) 0.0465(3) 0.00202(17) 0.00196(17) -0.00718(16)
O1 0.0693(17) 0.0498(15) 0.0504(16) 0.0000(16) 0.0111(14) 0.0039(13)
O2 0.0615(15) 0.0439(14) 0.0450(14) 0.0044(13) 0.0053(12) -0.0005(11)
C1 0.0461(16) 0.0401(16) 0.0416(17) -0.0034(14) -0.0038(14) 0.0009(14)
C2 0.0537(19) 0.0415(17) 0.0407(18) -0.0016(15) -0.0018(15) 0.0005(14)
C3 0.0498(18) 0.0424(18) 0.049(2) 0.0006(14) 0.0004(15) 0.0007(15)
C4 0.0489(16) 0.0489(18) 0.0395(17) -0.0091(16) -0.0003(15) -0.0062(15)
C5 0.0576(17) 0.0472(19) 0.0414(18) -0.0100(18) 0.0023(15) 0.0000(15)
C6 0.0585(17) 0.0381(17) 0.0464(19) -0.0005(15) 0.0005(16) 0.0028(14)
C7 0.0502(17) 0.0408(16) 0.0435(18) -0.0005(15) -0.0030(14) -0.0041(14)
C8 0.060(2) 0.052(2) 0.050(2) 0.0083(19) 0.0021(18) -0.0089(18)
C9 0.0530(17) 0.063(2) 0.054(2) -0.003(2) 0.0073(18) -0.011(2)
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'
Br Br -0.2901 2.4595 '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
C7 O2 C8 114.9(3)
C6 C1 C2 119.4(4)
C6 C1 C7 122.8(3)
C2 C1 C7 117.8(3)
C3 C2 C1 119.7(4)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 121.0(4)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.0(4)
C3 C4 C9 120.1(4)
C5 C4 C9 120.9(4)
C6 C5 C4 120.5(4)
C6 C5 H5 119.8
C4 C5 H5 119.8
C1 C6 C5 120.4(4)
C1 C6 H6 119.8
C5 C6 H6 119.8
O1 C7 O2 123.9(4)
O1 C7 C1 123.5(4)
O2 C7 C1 112.6(3)
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
C4 C9 Br1 110.1(3)
C4 C9 H9A 109.6
Br1 C9 H9A 109.6
C4 C9 H9B 109.6
Br1 C9 H9B 109.6
H9A C9 H9B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.973(5)
O1 C7 1.214(5)
O2 C7 1.326(5)
O2 C8 1.455(5)
C1 C6 1.386(5)
C1 C2 1.403(5)
C1 C7 1.492(5)
C2 C3 1.389(5)
C2 H2 0.9500
C3 C4 1.383(5)
C3 H3 0.9500
C4 C5 1.397(6)
C4 C9 1.493(6)
C5 C6 1.388(6)
C5 H5 0.9500
C6 H6 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9900
C9 H9B 0.9900
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
C6 C1 C2 C3 0.4(5)
C7 C1 C2 C3 -177.7(3)
C1 C2 C3 C4 -0.8(6)
C2 C3 C4 C5 0.1(6)
C2 C3 C4 C9 179.2(4)
C3 C4 C5 C6 0.9(6)
C9 C4 C5 C6 -178.2(4)
C2 C1 C6 C5 0.5(6)
C7 C1 C6 C5 178.6(4)
C4 C5 C6 C1 -1.2(6)
C8 O2 C7 O1 1.0(6)
C8 O2 C7 C1 -178.2(3)
C6 C1 C7 O1 172.7(4)
C2 C1 C7 O1 -9.2(6)
C6 C1 C7 O2 -8.2(5)
C2 C1 C7 O2 169.9(3)
C3 C4 C9 Br1 83.5(4)
C5 C4 C9 Br1 -97.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 225139
