#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/48/2004836.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_2004836
loop_
_publ_author_name
'Miguel, O. G.'
'Pizzolatti, M. G.'
'Yunes, R. A.'
'Vencato, I.'
'Calixto, J. B.'
'Santos, A. R. S.'
'Contin, A.'
'Moreira, E. A.'
_publ_contact_author
;
    Dr Ivo Vencato
    Depto. F\'isica - UFSC
    88040 - 900 Florian\'opolis, SC
    Brazil
;
_publ_section_title
;
 <i>cis</i>-8,10-Di-<i>n</i>-propyllobelidiol Hydrochloride Dihydrate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1223
_journal_page_last               1225
_journal_paper_doi               10.1107/S0108270195014636
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C16 H34 N O2 + , Cl - , 2H2 O'
_chemical_formula_moiety         'C16 H38 Cl N O4'
_chemical_formula_sum            'C16 H38 Cl N O4'
_chemical_formula_weight         343.93
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_type_scat_source
;
 International Tables for X-ray Crystallography (1974, Vol.IV)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.752(2)
_cell_length_b                   27.084(5)
_cell_length_c                   17.973(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      13.49
_cell_measurement_theta_min      9.70
_cell_volume                     4260.3(13)
_computing_cell_refinement       'MolEN   (Fair, 1990)'
_computing_data_collection       'CAD4-EXPRESS (Enraf-Nonius, 1993)'
_computing_data_reduction        MolEN
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  MolEN
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SIR92   (Altomare et al., 1992)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4237
_diffrn_reflns_theta_max         24.96
_diffrn_standards_decay_%        5.6
_diffrn_standards_interval_time  40
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       irregular
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.279
_refine_ls_extinction_coef       10.1E-8(5)
_refine_ls_extinction_method     'SHELX76  (Sheldrick, 1976)'
_refine_ls_goodness_of_fit_obs   4.45
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1617
_refine_ls_R_factor_obs          0.0609
_refine_ls_shift/esd_max         0.16
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 3.1873/[\s^2^(F) + 0.000353 F^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0670
_reflns_number_observed          1617
_reflns_number_total             2645
_reflns_observed_criterion       'F > 6.0\s(F)'
_cod_data_source_file            bk1156.cif
_cod_data_source_block           default
_cod_depositor_comments
;
 Commenting out the incomplete symmetry operator list:
        
 loop_
 _symmetry_equiv_pos_as_xyz
 '1/2 + x, y, 1/2 - z'

 Adding _atom_site_type_symbol with correct atoms types, to avoid
 misintepretation of 'HO2' as 'Ho' (Holmium).

 The spacegroup symbols seem to be correct.
 Saulius Gra\<zulis
 2012.04.25

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '3.1873/[\s^2^(F) + 0.000353
F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details'
was created. The value of the new tag was set to 'w =
3.1873/[\s^2^(F) + 0.000353 F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        4260(2)
_cod_database_code               2004836
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
Cl 0.0462(7) 0.0751(9) 0.0661(8) 0.0000(10) -0.0050(8) 0.0115(9)
Ow1 0.056(3) 0.102(3) 0.091(3) 0.007(2) -0.017(2) -0.037(3)
Ow2 0.052(2) 0.095(3) 0.077(3) -0.009(2) -0.011(2) 0.017(2)
O1 0.051(2) 0.072(3) 0.052(2) 0.006(2) 0.000(2) 0.002(2)
O2 0.045(2) 0.085(3) 0.055(2) 0.002(2) 0.002(2) -0.012(2)
N 0.048(3) 0.049(3) 0.032(2) -0.002(3) 0.005(2) 0.003(3)
C1 0.210(10) 0.087(7) 0.150(8) -0.033(8) -0.021(8) 0.008(7)
C2 0.120(7) 0.067(5) 0.089(5) -0.008(5) -0.014(5) -0.004(5)
C3 0.102(6) 0.055(4) 0.059(4) -0.005(4) -0.005(4) 0.006(3)
C4 0.053(4) 0.059(4) 0.050(4) 0.006(3) 0.003(3) -0.005(3)
C5 0.046(4) 0.062(4) 0.053(4) 0.004(3) 0.000(3) 0.001(3)
C6 0.040(4) 0.050(5) 0.053(4) 0.002(3) 0.001(3) 0.009(3)
C7 0.039(4) 0.077(5) 0.066(5) 0.004(4) 0.000(3) 0.008(4)
C8 0.036(3) 0.086(5) 0.065(4) -0.008(4) -0.003(3) 0.002(4)
C9 0.038(3) 0.081(6) 0.065(5) -0.011(3) 0.001(3) -0.002(4)
C10 0.041(4) 0.051(5) 0.040(3) 0.000(3) 0.004(3) 0.001(3)
C11 0.057(4) 0.060(4) 0.048(4) -0.006(3) 0.004(4) 0.005(4)
C12 0.052(4) 0.061(4) 0.064(4) -0.008(3) -0.002(4) -0.001(4)
C13 0.099(6) 0.041(4) 0.118(7) -0.001(4) -0.012(5) -0.009(4)
C14 0.135(8) 0.105(8) 0.200(10) 0.012(7) -0.033(8) 0.020(8)
C15 0.230(10) 0.087(7) 0.31(2) -0.007(9) -0.050(10) 0.060(10)
C16 0.079(4) 0.073(4) 0.037(3) -0.003(4) 0.008(3) 0.001(3)
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
Cl Cl 0.2483(2) 0.30926(5) 0.4073(1) 4.93(5)
O Ow1 -0.1835(4) 0.4108(1) 0.1787(2) 6.6(2)
O Ow2 -0.1843(4) 0.2082(1) 0.1817(2) 5.9(2)
O O1 0.0116(4) 0.4341(1) 0.2887(2) 4.6(1)
O O2 0.0134(4) 0.1801(1) 0.2910(2) 4.9(2)
N N -0.1017(4) 0.3087(2) 0.4091(2) 3.4(1)
C C1 0.011(1) 0.5832(3) 0.3767(5) 11.7(5)
C C2 -0.0260(9) 0.5349(3) 0.3383(4) 7.3(3)
C C3 -0.0300(8) 0.4912(2) 0.3886(3) 5.7(3)
C C4 -0.0890(7) 0.4452(2) 0.3505(3) 4.3(2)
C C5 -0.0941(6) 0.4011(2) 0.4031(3) 4.2(2)
C C6 -0.1520(6) 0.3543(2) 0.3666(3) 3.8(2)
C C7 -0.3266(7) 0.3536(3) 0.3553(3) 4.8(3)
C C8 -0.3764(6) 0.3072(3) 0.3144(3) 4.9(2)
C C9 -0.3221(7) 0.2614(2) 0.3566(3) 4.8(3)
C C10 -0.1480(6) 0.2623(2) 0.3675(3) 3.5(2)
C C11 -0.0847(7) 0.2168(2) 0.4053(3) 4.3(2)
C C12 -0.0809(7) 0.1711(2) 0.3556(3) 4.7(2)
C C13 -0.0186(9) 0.1272(2) 0.3991(4) 6.8(3)
C C14 -0.021(1) 0.0810(4) 0.3596(6) 11.7(5)
C C15 0.016(2) 0.0378(4) 0.4030(8) 16.6(7)
C C16 -0.1490(7) 0.3091(2) 0.4897(3) 5.0(2)
H HN 0.0216 0.3091 0.4115 5.9
H HO1 -0.0508 0.4300 0.2479 5.9
H HO2 -0.0509 0.1883 0.2479 5.9
H Hw11 -0.2602 0.4297 0.1716 5.9
H Hw21 -0.2030 0.3804 0.1531 5.9
H Hw12 -0.2661 0.1886 0.1716 5.9
H Hw22 -0.1991 0.2379 0.1531 5.9
H H1 0.0211 0.6158 0.3411 5.9
H H1' 0.1277 0.5810 0.4057 5.9
H H1" -0.0682 0.5920 0.4214 5.9
H H2 0.0621 0.5295 0.2936 5.9
H H2' -0.1339 0.5405 0.3093 5.9
H H3 -0.1047 0.4994 0.4353 5.9
H H3' 0.0835 0.4834 0.4099 5.9
H H4 -0.2047 0.4508 0.3300 5.9
H H5 0.0213 0.3958 0.4243 5.9
H H5' -0.1679 0.4110 0.4493 5.9
H H6 -0.0989 0.3536 0.3113 5.9
H H7 -0.3795 0.3549 0.4098 5.9
H H7' -0.3596 0.3858 0.3240 5.9
H H8 -0.3281 0.3057 0.2584 5.9
H H8' -0.5002 0.3053 0.3095 5.9
H H9 -0.3785 0.2590 0.4094 5.9
H H9' -0.3528 0.2276 0.3243 5.9
H H10 -0.1015 0.2636 0.3106 5.9
H H11 0.0316 0.2251 0.4245 5.9
H H11' -0.1538 0.2095 0.4549 5.9
H H12 -0.1955 0.1618 0.3357 5.9
H H13 -0.0896 0.1211 0.4500 5.9
H H13' 0.0966 0.1334 0.4174 5.9
H H14 -0.1388 0.0771 0.3339 5.9
H H14' 0.0556 0.0849 0.3110 5.9
H H15 0.0160 0.0027 0.3772 5.9
H H15' -0.0622 0.0341 0.4542 5.9
H H15" 0.1322 0.0420 0.4313 5.9
H H16 -0.1098 0.2751 0.5169 5.9
H H16' -0.2724 0.3108 0.4950 5.9
H H16" -0.0994 0.3401 0.5189 5.9
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
C4 O1 Ow1 117.7(3) no
C12 O2 Ow2 116.4(3) no
C6 N C10 110.4(4) yes
C6 N C16 113.5(4) yes
C10 N C16 114.0(4) yes
C1 C2 C3 114.5(7) yes
C2 C3 C4 112.8(6) yes
O1 C4 C3 108.1(5) yes
O1 C4 C5 109.3(4) yes
C3 C4 C5 112.0(5) yes
C4 C5 C6 113.4(5) yes
N C6 C5 111.5(4) yes
N C6 C7 110.1(4) yes
C5 C6 C7 113.5(5) yes
C6 C7 C8 111.0(5) yes
C7 C8 C9 110.0(5) yes
C8 C9 C10 111.0(5) yes
N C10 C9 109.9(4) yes
N C10 C11 110.8(4) yes
C9 C10 C11 114.1(5) yes
C10 C11 C12 113.9(5) yes
O2 C12 C11 110.2(5) yes
O2 C12 C13 109.8(5) yes
C11 C12 C13 109.9(5) yes
C12 C13 C14 114.8(7) yes
C13 C14 C15 115.8(9) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.449(7) yes
O2 C12 1.445(7) yes
N C6 1.517(7) yes
N C10 1.517(7) yes
N C16 1.507(6) yes
C1 C2 1.510(10) yes
C2 C3 1.490(10) yes
C3 C4 1.513(9) yes
C4 C5 1.524(8) yes
C5 C6 1.515(8) yes
C6 C7 1.542(8) yes
C7 C8 1.520(9) yes
C8 C9 1.530(9) yes
C9 C10 1.536(8) yes
C10 C11 1.512(8) yes
C11 C12 1.527(9) yes
C12 C13 1.524(9) yes
C13 C14 1.440(10) yes
C14 C15 1.44(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139054888