#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/41/2214161.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_2214161
loop_
_publ_author_name
'Ben Amor, Fatma'
'Jmour, Asma'
'Driss, Ahmed'
'Rezgui, Farhat'
_publ_section_title
;
 Ethyle
 4-bromo-3-hydroxy-5,6,7,8-tétrahydronaphtalène-2-carboxylate
;
_journal_coeditor_code           DN2193
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3314
_journal_page_last               o3314
_journal_paper_doi               10.1107/S1600536807029777
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H15 Br O3'
_chemical_formula_moiety         'C13 H15 Br O3'
_chemical_formula_sum            'C13 H15 Br O3'
_chemical_formula_weight         299.16
_chemical_name_systematic
;
Ethyl 4-bromo-3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carboxylate
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.840(6)
_cell_length_b                   7.141(3)
_cell_length_c                   9.364(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14.73
_cell_measurement_theta_min      10.48
_cell_volume                     1265.3(8)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3614
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_T_max  0.9995
_exptl_absorpt_correction_T_min  0.5669
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.051P)²+1.9759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                1070
_reflns_number_total             1483
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2193.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2214161
_cod_database_fobs_code          2214161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.59010(3) 0.5000 0.98075(8) 0.0748(3) Uani d S 1 . .
O O1 0.8758(2) 0.5000 1.3330(4) 0.0636(10) Uani d S 1 . .
O O2 0.92499(17) 0.5000 1.1618(4) 0.0572(9) Uani d S 1 . .
O O3 0.7377(2) 0.5000 1.2234(4) 0.0630(10) Uani d S 1 . .
H H3 0.7785 0.5000 1.2911 0.076 Uiso calc SR 1 . .
C C1 0.7968(2) 0.5000 0.9059(5) 0.0468(11) Uani d S 1 . .
H H1 0.8385 0.5000 0.8924 0.056 Uiso calc SR 1 . .
C C2 0.8008(2) 0.5000 1.0587(5) 0.0417(10) Uani d S 1 . .
C C3 0.7380(3) 0.5000 1.0790(5) 0.0449(11) Uani d S 1 . .
C C4 0.6740(2) 0.5000 0.9467(6) 0.0445(11) Uani d S 1 . .
C C5 0.5989(2) 0.5000 0.6514(6) 0.0544(12) Uani d S 1 . .
H H5A 0.5761 0.3798 0.6447 0.065 Uiso calc PR 0.50 A .
H H5B 0.5689 0.5955 0.6655 0.065 Uiso calc PR 0.50 . .
C C6 0.6056(4) 0.536(5) 0.4988(8) 0.084(10) Uani d P 0.50 A -1
H H6A 0.5871 0.4255 0.4348 0.101 Uiso calc PR 0.50 A -1
H H6B 0.5726 0.6367 0.4470 0.101 Uiso calc PR 0.50 A -1
C C7 0.6621(3) 0.5774(12) 0.4855(7) 0.062(2) Uani d P 0.50 A -1
H H7A 0.6656 0.7128 0.4853 0.074 Uiso calc PR 0.50 A -1
H H7B 0.6572 0.5338 0.3834 0.074 Uiso calc PR 0.50 A -1
C C8 0.7335(3) 0.5000 0.6118(6) 0.0624(15) Uani d S 1 . .
H H8A 0.7408 0.3734 0.5841 0.075 Uiso calc PR 0.50 A .
H H8B 0.7722 0.5770 0.6136 0.075 Uiso calc PR 0.50 . .
C C9 0.7332(2) 0.5000 0.7743(5) 0.0432(10) Uani d S 1 A .
C C10 0.6699(2) 0.5000 0.7937(5) 0.0422(10) Uani d S 1 A .
C C11 0.8699(3) 0.5000 1.1980(6) 0.0492(11) Uani d S 1 . .
C C12 0.9947(3) 0.5000 1.2930(6) 0.0611(14) Uani d S 1 . .
H H12A 1.0005 0.3897 1.3578 0.073 Uiso calc PR 0.50 . .
H H12B 1.0005 0.6103 1.3578 0.073 Uiso calc PR 0.50 . .
C C13 1.0479(3) 0.5000 1.2249(7) 0.085(2) Uani d S 1 . .
H H13A 1.0946 0.5000 1.3084 0.127 Uiso calc SR 1 . .
H H13B 1.0416 0.6098 1.1613 0.127 Uiso calc PR 0.50 . .
H H13C 1.0416 0.3902 1.1613 0.127 Uiso calc PR 0.50 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C11 O2 C12 . . 116.7(4)
C3 O3 H3 . . 109.5
C9 C1 C2 . . 122.6(4)
C9 C1 H1 . . 118.7
C2 C1 H1 . . 118.7
C1 C2 C3 . . 118.7(4)
C1 C2 C11 . . 121.4(4)
C3 C2 C11 . . 119.9(4)
O3 C3 C4 . . 119.0(4)
O3 C3 C2 . . 122.1(4)
C4 C3 C2 . . 118.8(4)
C3 C4 C10 . . 122.5(4)
C3 C4 Br1 . . 117.2(3)
C10 C4 Br1 . . 120.3(3)
C6 C5 C6 6_565 . 20(3)
C6 C5 C10 6_565 . 112.7(4)
C6 C5 C10 . . 112.7(4)
C6 C5 H5A 6_565 . 91.3
C6 C5 H5A . . 109.1
C10 C5 H5A . . 109.1
C6 C5 H5B 6_565 . 124.6
C6 C5 H5B . . 109.1
C10 C5 H5B . . 109.1
H5A C5 H5B . . 107.8
C7 C6 C5 . . 126.0(6)
C7 C6 H6A . . 105.8
C5 C6 H6A . . 105.8
C7 C6 H6B . . 105.8
C5 C6 H6B . . 105.8
H6A C6 H6B . . 106.2
C6 C7 C8 . . 118.2(11)
C6 C7 H7A . . 107.8
C8 C7 H7A . . 107.8
C6 C7 H7B . . 107.8
C8 C7 H7B . . 107.8
H7A C7 H7B . . 107.1
C9 C8 C7 . 6_565 110.7(4)
C9 C8 C7 . . 110.7(4)
C7 C8 C7 6_565 . 41.4(6)
C9 C8 H8A . . 109.5
C7 C8 H8A 6_565 . 71.0
C7 C8 H8A . . 109.5
C9 C8 H8B . . 109.5
C7 C8 H8B 6_565 . 137.3
C7 C8 H8B . . 109.5
H8A C8 H8B . . 108.1
C1 C9 C10 . . 119.1(4)
C1 C9 C8 . . 119.2(4)
C10 C9 C8 . . 121.7(4)
C4 C10 C9 . . 118.3(4)
C4 C10 C5 . . 121.2(4)
C9 C10 C5 . . 120.6(4)
O1 C11 O2 . . 122.9(5)
O1 C11 C2 . . 123.5(5)
O2 C11 C2 . . 113.6(4)
O2 C12 C13 . . 107.2(4)
O2 C12 H12A . . 110.3
C13 C12 H12A . . 110.3
O2 C12 H12B . . 110.3
C13 C12 H12B . . 110.3
H12A C12 H12B . . 108.5
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.905(4)
O1 C11 . 1.218(6)
O2 C11 . 1.327(6)
O2 C12 . 1.457(6)
O3 C3 . 1.356(5)
O3 H3 . 0.8200
C1 C9 . 1.380(7)
C1 C2 . 1.397(6)
C1 H1 . 0.9300
C2 C3 . 1.399(6)
C2 C11 . 1.483(7)
C3 C4 . 1.388(7)
C4 C10 . 1.399(6)
C5 C6 6_565 1.516(10)
C5 C6 . 1.516(10)
C5 C10 . 1.520(7)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C7 . 1.268(12)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.563(8)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.525(6)
C8 C7 6_565 1.563(8)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.405(6)
C12 C13 . 1.492(8)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 0.82 1.90 2.620(5) 146.3
