#------------------------------------------------------------------------------
#$Date: 2019-12-26 22:19:39 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246169 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/19/2311924.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_2311924
loop_
_publ_author_name
'Jandl, Christian'
'Pöthig, Alexander'
_publ_section_title
;
 Hydroxytropylium chloride: the first crystal structure of an
 unfunctionalized hydroxytropylium ion.
;
_journal_coeditor_code           FP3042
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              810
_journal_page_last               813
_journal_paper_doi               10.1107/S2053229617013183
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C7 H7 O +, Cl -'
_chemical_formula_moiety         'C7 H7 O +, Cl -'
_chemical_formula_sum            'C7 H7 Cl O'
_chemical_formula_weight         142.58
_chemical_name_systematic
;
Hydroxytropylium chloride
;
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 98.727(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8622(3)
_cell_length_b                   6.9718(4)
_cell_length_c                   10.1539(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    123
_cell_measurement_theta_max      36.3569
_cell_measurement_theta_min      2.9217
_cell_volume                     340.21(3)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
PLATON (Spek, 2009), enCIFer (Allen et al.,  2004) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)and ShelXle (Hübschle et al.,
2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'MONTEL optic'
_diffrn_radiation_source         'rotating anode FR591'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14261
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.147
_refine_ls_abs_structure_details
;
Flack (1983) and Parsons et al. (2013)
;
_refine_ls_abs_structure_Flack   0.097(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1690
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0212
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'W=1/[Σ²(FO²)+(0.0407P)²+0.0399P] WHERE P=(FO²+2FC²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0585
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                1682
_reflns_number_total             1690
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fp3042sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        340.22(3)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2311924
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x,-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.83894(12) 1.00722(6) 0.32306(7) 0.02690(10) Uani d . 1.000
O O1 0.7122(3) 0.61466(18) 0.37565(14) 0.0242(3) Uani d . 1.000
C C1 0.5421(3) 0.5794(3) 0.46254(16) 0.0191(5) Uani d . 1.000
C C2 0.4481(3) 0.7335(2) 0.53459(17) 0.0222(5) Uani d . 1.000
C C3 0.2685(4) 0.7279(3) 0.62647(18) 0.0240(5) Uani d . 1.000
C C4 0.1276(3) 0.5721(3) 0.67384(16) 0.0227(5) Uani d . 1.000
C C5 0.1451(3) 0.3822(3) 0.64158(19) 0.0242(5) Uani d . 1.000
C C6 0.3053(4) 0.2993(2) 0.5518(2) 0.0249(5) Uani d . 1.000
C C7 0.4782(4) 0.3835(3) 0.47408(18) 0.0223(5) Uani d . 1.000
H H1 0.751(6) 0.738(5) 0.370(4) 0.063(9) Uiso d . 1.000
H H2 0.51830 0.85660 0.51710 0.0270 Uiso c RU 1.000
H H3 0.23370 0.84860 0.66420 0.0290 Uiso c RU 1.000
H H4 0.00560 0.60230 0.73560 0.0270 Uiso c RU 1.000
H H5 0.03630 0.29610 0.68480 0.0290 Uiso c RU 1.000
H H6 0.29120 0.16370 0.54410 0.0300 Uiso c RU 1.000
H H7 0.56700 0.29840 0.42070 0.0270 Uiso c RU 1.000
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'
Cl Cl 0.1484 0.1585 ' 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
_geom_angle_publ_flag
C1 O1 H1 113(2) no
O1 C1 C2 119.24(17) yes
O1 C1 C7 113.84(16) yes
C2 C1 C7 126.91(15) yes
C1 C2 C3 128.26(15) yes
C2 C3 C4 130.36(18) yes
C3 C4 C5 127.82(16) yes
C4 C5 C6 127.70(16) yes
C5 C6 C7 130.14(16) yes
C1 C7 C6 128.73(17) yes
C1 C2 H2 116.00 no
C3 C2 H2 116.00 no
C2 C3 H3 115.00 no
C4 C3 H3 115.00 no
C3 C4 H4 116.00 no
C5 C4 H4 116.00 no
C4 C5 H5 116.00 no
C6 C5 H5 116.00 no
C5 C6 H6 115.00 no
C7 C6 H6 115.00 no
C1 C7 H7 116.00 no
C6 C7 H7 116.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.321(2) yes
O1 H1 0.88(3) no
C1 C7 1.410(3) yes
C1 C2 1.414(2) yes
C2 C3 1.372(2) yes
C3 C4 1.407(3) yes
C4 C5 1.370(3) yes
C5 C6 1.410(3) yes
C6 C7 1.370(3) yes
C2 H2 0.9500 no
C3 H3 0.9500 no
C4 H4 0.9500 no
C5 H5 0.9500 no
C6 H6 0.9500 no
C7 H7 0.9500 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
O1 H1 Cl1 . 0.88(3) 2.00(3) 2.8732(14) 170(4) yes
C2 H2 Cl1 . 0.9500 2.8892 3.620(2) 134.6 yes
C3 H3 Cl1 2_475 0.9500 2.8698 3.609(2) 135.4 yes
C4 H4 O1 2_465 0.9500 2.638 3.351(2) 132.2 yes
C5 H5 Cl1 2_465 0.9500 2.7900 3.717(2) 165.9 yes
C7 H7 Cl1 1_545 0.9500 2.6900 3.623(2) 166.3 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
_geom_torsion_publ_flag
O1 C1 C2 C3 178.61(17) yes
C7 C1 C2 C3 -2.7(3) yes
O1 C1 C7 C6 -178.33(19) yes
C2 C1 C7 C6 2.9(3) yes
C1 C2 C3 C4 -0.5(3) yes
C2 C3 C4 C5 2.6(3) yes
C3 C4 C5 C6 -1.1(3) yes
C4 C5 C6 C7 -0.8(3) yes
C5 C6 C7 C1 -0.3(4) yes
