#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226478.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_2226478
loop_
_publ_author_name
'Abbasi, Muhammad Athar'
Aziz-ur-Rehman
'Akkurt, Mehmet'
'Jahangir, Muhammad'
'Ng, Seik Weng'
'Khan, Islam Ullah'
_publ_section_title
;
 Ammonium
 [(1S)-(endo,anti)]-({-})-3-bromocamphor-8-sulfonate
;
_journal_coeditor_code           HB5484
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1707
_journal_page_last               o1708
_journal_paper_doi               10.1107/S1600536810022804
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'N1 H4 +, C10 H14 Br O4 S -'
_chemical_formula_moiety         'H4 N +, C10 H14 Br O4 S -'
_chemical_formula_sum            'C10 H18 Br N O4 S'
_chemical_formula_weight         328.22
_chemical_name_common
;
Ammonium [(1S)-(endo,anti)]-(-)-3-bromocamphor-8-sulfonate
;
_chemical_name_systematic
;
Ammonium [(1S)-(endo,anti)]-(-)-(3-bromo-1,7-
dimethyl-2-oxobicyclo[2.2.1]heptan-7-yl)methanesulfonate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 104.7040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2449(2)
_cell_length_b                   7.00490(10)
_cell_length_c                   13.2428(3)
_cell_measurement_reflns_used    3356
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.91
_cell_volume                     650.06(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999), PARST (Nardelli, 1983) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2775
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    3.325
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
(XABS2; Parkin et al.,  1995; quadratic fit to sin(θ)/λ - 18
parameters)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.471
_refine_ls_abs_structure_details 'Flack (1983), 1155 Freidel pairs'
_refine_ls_abs_structure_Flack   -0.021(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0274
_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)+(0.0330P)²+0.1814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                2586
_reflns_number_total             2775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5484.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2226478
_cod_database_fobs_code          2226478
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.09450(4) 0.00017(4) 0.27520(3) 0.04400(10) Uani . . 1.000
S S1 0.65799(9) 0.68509(9) 0.36429(5) 0.0242(2) Uani . . 1.000
O O1 0.7216(3) 0.8793(3) 0.3541(2) 0.0434(8) Uani . . 1.000
O O2 0.8199(3) 0.5560(3) 0.39714(16) 0.0332(6) Uani . . 1.000
O O3 0.5283(3) 0.6697(4) 0.42972(17) 0.0448(8) Uani . . 1.000
O O4 0.2268(4) 0.0517(4) 0.0568(2) 0.0596(10) Uani . . 1.000
C C1 0.5311(4) 0.6201(4) 0.2339(2) 0.0277(8) Uani . . 1.000
C C2 0.4754(4) 0.4086(4) 0.2154(2) 0.0213(7) Uani . . 1.000
C C3 0.3597(3) 0.3263(4) 0.2899(2) 0.0223(7) Uani . . 1.000
C C4 0.1802(4) 0.4500(4) 0.2647(2) 0.0272(8) Uani . . 1.000
C C5 0.1351(4) 0.4758(5) 0.1462(2) 0.0352(9) Uani . . 1.000
C C6 0.3067(4) 0.3804(4) 0.1148(2) 0.0310(9) Uani . . 1.000
C C7 0.3318(6) 0.4411(6) 0.0112(2) 0.0519(13) Uani . . 1.000
C C8 0.6514(4) 0.2949(4) 0.2067(2) 0.0316(9) Uani . . 1.000
C C9 0.2719(4) 0.1690(5) 0.1248(2) 0.0342(9) Uani . . 1.000
C C10 0.3097(4) 0.1283(4) 0.2418(2) 0.0298(8) Uani . . 1.000
N N1 0.8032(3) 0.1906(4) 0.4952(2) 0.0311(7) Uani . . 1.000
H H1A 0.41550 0.69600 0.21450 0.0330 Uiso calc R 1.000
H H1B 0.60920 0.65480 0.18710 0.0330 Uiso calc R 1.000
H H3 0.42880 0.32500 0.36380 0.0270 Uiso calc R 1.000
H H4A 0.20390 0.57210 0.30010 0.0330 Uiso calc R 1.000
H H4B 0.07600 0.38650 0.28480 0.0330 Uiso calc R 1.000
H H5A 0.12590 0.61000 0.12770 0.0420 Uiso calc R 1.000
H H5B 0.01620 0.41320 0.11210 0.0420 Uiso calc R 1.000
H H7A 0.22080 0.40620 -0.04250 0.0780 Uiso calc R 1.000
H H7B 0.44200 0.37920 -0.00150 0.0780 Uiso calc R 1.000
H H7C 0.34880 0.57700 0.01080 0.0780 Uiso calc R 1.000
H H8A 0.74270 0.29220 0.27340 0.0470 Uiso calc R 1.000
H H8B 0.70750 0.35440 0.15630 0.0470 Uiso calc R 1.000
H H8C 0.61420 0.16680 0.18500 0.0470 Uiso calc R 1.000
H H10 0.42240 0.04610 0.26290 0.0360 Uiso calc R 1.000
H H1N 0.775(5) 0.096(4) 0.445(2) 0.0470 Uiso . . 1.000
H H2N 0.914(4) 0.170(6) 0.543(2) 0.0470 Uiso . . 1.000
H H3N 0.806(5) 0.305(4) 0.461(3) 0.0470 Uiso . . 1.000
H H4N 0.706(4) 0.195(6) 0.528(3) 0.0470 Uiso . . 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . . 111.00(13) no
O1 S1 O3 . . . 113.46(15) no
O1 S1 C1 . . . 104.17(14) no
O2 S1 O3 . . . 111.96(14) no
O2 S1 C1 . . . 107.84(13) no
O3 S1 C1 . . . 107.92(14) no
H3N N1 H4N . . . 109(3) no
H2N N1 H4N . . . 109(3) no
H1N N1 H3N . . . 107(3) no
H1N N1 H4N . . . 108(3) no
H1N N1 H2N . . . 113(3) no
H2N N1 H3N . . . 111(3) no
S1 C1 C2 . . . 116.52(19) no
C1 C2 C8 . . . 108.8(2) no
C1 C2 C6 . . . 111.8(2) no
C1 C2 C3 . . . 114.6(2) no
C6 C2 C8 . . . 110.7(2) no
C3 C2 C6 . . . 93.6(2) no
C3 C2 C8 . . . 116.6(2) no
C4 C3 C10 . . . 108.9(2) no
C2 C3 C4 . . . 102.5(2) no
C2 C3 C10 . . . 100.4(2) no
C3 C4 C5 . . . 103.9(2) no
C4 C5 C6 . . . 104.2(2) no
C7 C6 C9 . . . 114.9(3) no
C2 C6 C7 . . . 119.5(3) no
C2 C6 C5 . . . 102.8(2) no
C5 C6 C9 . . . 103.6(2) no
C2 C6 C9 . . . 99.2(2) no
C5 C6 C7 . . . 114.5(3) no
O4 C9 C6 . . . 128.6(3) no
O4 C9 C10 . . . 125.2(3) no
C6 C9 C10 . . . 106.3(2) no
Br1 C10 C3 . . . 116.24(18) no
Br1 C10 C9 . . . 111.62(19) no
C3 C10 C9 . . . 102.4(2) no
S1 C1 H1B . . . 108.00 no
S1 C1 H1A . . . 108.00 no
C2 C1 H1A . . . 108.00 no
C2 C1 H1B . . . 108.00 no
H1A C1 H1B . . . 107.00 no
C10 C3 H3 . . . 114.00 no
C4 C3 H3 . . . 114.00 no
C2 C3 H3 . . . 115.00 no
C5 C4 H4A . . . 111.00 no
C3 C4 H4B . . . 111.00 no
C3 C4 H4A . . . 111.00 no
C5 C4 H4B . . . 111.00 no
H4A C4 H4B . . . 109.00 no
H5A C5 H5B . . . 109.00 no
C4 C5 H5A . . . 111.00 no
C4 C5 H5B . . . 111.00 no
C6 C5 H5A . . . 111.00 no
C6 C5 H5B . . . 111.00 no
H7B C7 H7C . . . 109.00 no
C6 C7 H7C . . . 109.00 no
C6 C7 H7A . . . 110.00 no
C6 C7 H7B . . . 109.00 no
H7A C7 H7B . . . 109.00 no
H7A C7 H7C . . . 109.00 no
C2 C8 H8B . . . 109.00 no
C2 C8 H8A . . . 109.00 no
H8A C8 H8C . . . 109.00 no
C2 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
H8B C8 H8C . . . 110.00 no
C9 C10 H10 . . . 109.00 no
Br1 C10 H10 . . . 109.00 no
C3 C10 H10 . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C10 . . 1.945(3) no
S1 O1 . . 1.454(2) no
S1 O2 . . 1.457(2) no
S1 O3 . . 1.435(2) no
S1 C1 . . 1.797(3) no
O4 C9 . . 1.201(4) no
N1 H1N . . 0.92(3) no
N1 H2N . . 0.90(3) no
N1 H3N . . 0.92(3) no
N1 H4N . . 0.92(3) no
C1 C2 . . 1.539(4) no
C2 C3 . . 1.558(4) no
C2 C6 . . 1.575(4) no
C2 C8 . . 1.532(4) no
C3 C4 . . 1.527(4) no
C3 C10 . . 1.531(4) no
C4 C5 . . 1.530(4) no
C5 C6 . . 1.558(4) no
C6 C7 . . 1.491(4) no
C6 C9 . . 1.514(4) no
C9 C10 . . 1.530(4) no
C1 H1B . . 0.9700 no
C1 H1A . . 0.9700 no
C3 H3 . . 0.9800 no
C4 H4B . . 0.9700 no
C4 H4A . . 0.9700 no
C5 H5A . . 0.9700 no
C5 H5B . . 0.9700 no
C7 H7A . . 0.9600 no
C7 H7B . . 0.9600 no
C7 H7C . . 0.9600 no
C8 H8B . . 0.9600 no
C8 H8C . . 0.9600 no
C8 H8A . . 0.9600 no
C10 H10 . . 0.9800 no
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 H1N O1 1_545 0.92(3) 1.92(3) 2.835(4) 173(3) yes
N1 H2N O2 2_746 0.90(3) 2.05(3) 2.899(3) 157(3) yes
N1 H3N O2 . 0.92(3) 1.97(3) 2.887(3) 176(3) yes
N1 H4N O3 2_646 0.92(3) 1.93(3) 2.827(3) 167(4) yes
C4 H4B Br1 . 0.97 2.71 3.221(3) 113 yes
C8 H8A O2 . 0.96 2.44 3.104(3) 126 yes
C10 H10 O1 1_545 0.98 2.49 3.451(4) 167 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C1 C2 . . . . 169.7(2) no
O2 S1 C1 C2 . . . . 51.7(2) no
O3 S1 C1 C2 . . . . -69.4(3) no
S1 C1 C2 C3 . . . . 54.3(3) no
S1 C1 C2 C6 . . . . 159.2(2) no
S1 C1 C2 C8 . . . . -78.2(3) no
C1 C2 C3 C4 . . . . 61.2(3) no
C1 C2 C3 C10 . . . . 173.5(2) no
C6 C2 C3 C4 . . . . -54.8(2) no
C6 C2 C3 C10 . . . . 57.5(2) no
C8 C2 C3 C4 . . . . -170.0(2) no
C8 C2 C3 C10 . . . . -57.8(3) no
C1 C2 C6 C5 . . . . -67.8(3) no
C1 C2 C6 C7 . . . . 60.4(4) no
C1 C2 C6 C9 . . . . -174.0(2) no
C3 C2 C6 C5 . . . . 50.6(2) no
C3 C2 C6 C7 . . . . 178.7(3) no
C3 C2 C6 C9 . . . . -55.7(2) no
C8 C2 C6 C5 . . . . 170.7(2) no
C8 C2 C6 C7 . . . . -61.1(4) no
C8 C2 C6 C9 . . . . 64.5(3) no
C2 C3 C4 C5 . . . . 39.1(3) no
C10 C3 C4 C5 . . . . -66.7(3) no
C2 C3 C10 Br1 . . . . -159.47(17) no
C2 C3 C10 C9 . . . . -37.5(3) no
C4 C3 C10 Br1 . . . . -52.3(3) no
C4 C3 C10 C9 . . . . 69.7(3) no
C3 C4 C5 C6 . . . . -5.6(3) no
C4 C5 C6 C2 . . . . -29.3(3) no
C4 C5 C6 C7 . . . . -160.5(3) no
C4 C5 C6 C9 . . . . 73.6(3) no
C2 C6 C9 O4 . . . . -144.1(3) no
C2 C6 C9 C10 . . . . 34.8(3) no
C5 C6 C9 O4 . . . . 110.3(4) no
C5 C6 C9 C10 . . . . -70.9(3) no
C7 C6 C9 O4 . . . . -15.4(5) no
C7 C6 C9 C10 . . . . 163.5(3) no
O4 C9 C10 Br1 . . . . -54.7(4) no
O4 C9 C10 C3 . . . . -179.8(3) no
C6 C9 C10 Br1 . . . . 126.4(2) no
C6 C9 C10 C3 . . . . 1.3(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26404022
