#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/18/2011848.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_2011848
loop_
_publ_author_name
'Belin, Renaud'
'Tillard, Monique'
'Maurel, Jean-Louis'
'Ribet, Jean-Paul'
_publ_section_title
;
 Absolute configuration of
 (+)-(S)-2-(5-fluoro-2-methoxy-1,4-benzodioxan-2-yl)imidazolinium
 bromide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              483
_journal_page_last               484
_journal_paper_doi               10.1107/S0108270101000981
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C12 H14 F N2 O3 + , Br - '
_chemical_formula_sum            'C12 H14 Br F N2 O3'
_chemical_formula_weight         333.16
_chemical_name_systematic
;
 ?
;
_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'
_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                   8.220(3)
_cell_length_b                   9.365(3)
_cell_length_c                   17.890(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.62
_cell_measurement_theta_min      6.05
_cell_volume                     1377.2(7)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEP (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Nonius CAD 4 diffractometer'
_diffrn_measurement_method       ω-θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0237
_diffrn_reflns_av_sigmaI/netI    .0723
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3134
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.00
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_refine_diff_density_max         .643
_refine_diff_density_min         -.580
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .007(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .968
_refine_ls_R_factor_all          .0881
_refine_ls_R_factor_gt           .0385
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0477P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0960
_reflns_number_gt                1869
_reflns_number_total             2689
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bk1579.cif
_cod_data_source_block           f14413
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0477P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0477P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2011848
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_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
_atom_site_type_symbol
Br 1.22657(5) .81042(6) -.15534(3) .05013(17) Uani d . 1 . . Br
N1 .5947(4) .6879(5) -.1645(3) .0509(11) Uani d . 1 . . N
N2 .8545(4) .6788(5) -.1456(3) .0509(11) Uani d . 1 . . N
C9 .7186(6) .7471(5) -.1327(2) .0379(10) Uani d . 1 . . C
O1 .5874(5) .9866(4) .02402(19) .0527(10) Uani d . 1 . . O
C7 .5868(6) .8658(5) -.0232(3) .0442(13) Uani d . 1 . . C
H7A .4785 .8526 -.0436 .053 Uiso calc R 1 . . H
H7B .6138 .7816 .0058 .053 Uiso calc R 1 . . H
C6 .7353(7) 1.0451(5) .0358(2) .0488(13) Uani d . 1 . . C
C10 .6416(6) .5599(6) -.2064(3) .0515(15) Uani d . 1 . . C
H10A .6120 .5679 -.2588 .062 Uiso calc R 1 . . H
H10B .5922 .4748 -.1856 .062 Uiso calc R 1 . . H
O2 .8661(4) .9007(3) -.05711(19) .0448(9) Uani d . 1 . . O
O3 .6586(4) .9970(4) -.12964(17) .0450(8) Uani d . 1 . . O
F .6196(6) 1.1926(5) .1267(2) .0975(13) Uani d . 1 . . F
C8 .7072(5) .8814(5) -.0866(2) .0360(10) Uani d . 1 . . C
C1 .7539(9) 1.1549(6) .0880(3) .0716(18) Uani d . 1 . . C
C12 .7661(8) 1.0357(6) -.1898(3) .0714(18) Uani d . 1 . . C
H12A .8769 1.0219 -.1743 .107 Uiso calc R 1 . . H
H12B .7494 1.1341 -.2026 .107 Uiso calc R 1 . . H
H12C .7438 .9769 -.2325 .107 Uiso calc R 1 . . H
C5 .8745(7) 1.0061(6) -.0034(3) .0439(13) Uani d . 1 . . C
C4 1.0218(8) 1.0721(6) .0076(3) .0618(16) Uani d . 1 . . C
H4 1.1131 1.0442 -.0194 .074 Uiso calc R 1 . . H
C3 1.0316(9) 1.1799(8) .0593(4) .081(2) Uani d . 1 . . C
H3 1.1312 1.2243 .0678 .098 Uiso calc R 1 . . H
C11 .8275(6) .5590(7) -.1961(4) .070(2) Uani d . 1 . . C
H11A .8642 .4700 -.1741 .084 Uiso calc R 1 . . H
H11B .8831 .5734 -.2434 .084 Uiso calc R 1 . . H
C2 .8975(11) 1.2235(7) .0987(4) .085(2) Uani d . 1 . . C
H2 .9048 1.2989 .1324 .102 Uiso calc R 1 . . H
HN1 .505(6) .712(5) -.159(3) .050 Uiso d . 1 . . H
HN2 .950(6) .710(5) -.126(3) .050 Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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
_geom_angle_publ_flag
HN1 Br HN2 1_655 . 134.8(16) n
HN1 Br N1 1_655 1_655 1.9(12) n
HN2 Br N1 . 1_655 136.2(11) n
HN1 Br N2 1_655 . 136.2(12) n
HN2 Br N2 . . 9.1(11) n
N1 Br N2 1_655 . 137.33(11) n
C9 N1 C10 . . 111.7(4) n
C9 N1 HN1 . . 124(4) n
C10 N1 HN1 . . 124(4) n
C9 N2 C11 . . 110.9(4) n
C9 N2 Br . . 128.1(3) n
C11 N2 Br . . 113.3(3) n
C9 N2 HN2 . . 121(3) n
C11 N2 HN2 . . 128(3) n
Br N2 HN2 . . 26(3) n
N1 C9 N2 . . 112.6(4) n
N1 C9 C8 . . 123.4(4) n
N2 C9 C8 . . 123.9(4) n
C6 O1 C7 . . 114.9(4) n
O1 C7 C8 . . 111.6(4) n
O1 C7 H7A . . 109.3 n
C8 C7 H7A . . 109.3 n
O1 C7 H7B . . 109.3 n
C8 C7 H7B . . 109.3 n
H7A C7 H7B . . 108.0 n
O1 C6 C5 . . 123.8(4) n
O1 C6 C1 . . 120.1(5) n
C5 C6 C1 . . 116.1(6) n
N1 C10 C11 . . 101.8(4) n
N1 C10 H10A . . 111.4 n
C11 C10 H10A . . 111.4 n
N1 C10 H10B . . 111.4 n
C11 C10 H10B . . 111.4 n
H10A C10 H10B . . 109.3 n
C5 O2 C8 . . 113.3(4) n
C8 O3 C12 . . 115.8(4) n
O3 C8 O2 . . 111.8(4) n
O3 C8 C9 . . 111.4(3) n
O2 C8 C9 . . 104.6(4) n
O3 C8 C7 . . 107.7(4) n
O2 C8 C7 . . 109.6(4) n
C9 C8 C7 . . 111.7(4) n
F C1 C2 . . 121.0(5) n
F C1 C6 . . 116.5(6) n
C2 C1 C6 . . 122.5(6) n
O3 C12 H12A . . 109.5 n
O3 C12 H12B . . 109.5 n
H12A C12 H12B . . 109.5 n
O3 C12 H12C . . 109.5 n
H12A C12 H12C . . 109.5 n
H12B C12 H12C . . 109.5 n
C4 C5 O2 . . 117.8(5) n
C4 C5 C6 . . 122.3(5) n
O2 C5 C6 . . 119.8(5) n
C3 C4 C5 . . 118.7(6) n
C3 C4 H4 . . 120.6 n
C5 C4 H4 . . 120.6 n
C2 C3 C4 . . 121.2(6) n
C2 C3 H3 . . 119.4 n
C4 C3 H3 . . 119.4 n
N2 C11 C10 . . 102.7(4) n
N2 C11 H11A . . 111.2 n
C10 C11 H11A . . 111.2 n
N2 C11 H11B . . 111.2 n
C10 C11 H11B . . 111.2 n
H11A C11 H11B . . 109.1 n
C1 C2 C3 . . 119.1(6) n
C1 C2 H2 . . 120.5 n
C3 C2 H2 . . 120.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br HN1 1_655 2.47(5) n
Br HN2 . 2.52(5) n
Br N1 1_655 3.240(4) y
Br N2 . 3.302(4) y
N1 C9 . 1.292(6) y
N1 C10 . 1.465(7) y
N1 HN1 . .78(5) y
N2 C9 . 1.308(6) y
N2 C11 . 1.458(7) y
N2 HN2 . .91(5) y
C9 C8 . 1.506(6) y
O1 C6 . 1.350(7) y
O1 C7 . 1.412(6) y
C7 C8 . 1.513(6) y
C7 H7A . .9700 n
C7 H7B . .9700 n
C6 C5 . 1.391(8) y
C6 C1 . 1.397(7) y
C10 C11 . 1.539(7) y
C10 H10A . .9700 n
C10 H10B . .9700 n
O2 C5 . 1.379(6) y
O2 C8 . 1.420(5) y
O3 C8 . 1.387(5) y
O3 C12 . 1.438(6) y
F C1 . 1.350(7) y
C1 C2 . 1.358(9) y
C12 H12A . .9600 n
C12 H12B . .9600 n
C12 H12C . .9600 n
C5 C4 . 1.373(8) y
C4 C3 . 1.371(8) y
C4 H4 . .9300 n
C3 C2 . 1.371(10) y
C3 H3 . .9300 n
C11 H11A . .9700 n
C11 H11B . .9700 n
C2 H2 . .9300 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 HN1 Br 1_455 .77(5) 2.47(5) 3.240(4) 172(5) y
N2 HN2 Br . .91(5) 2.52(5) 3.302(4) 145(4) y
