#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/58/2005836.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_2005836
loop_
_publ_author_name
'Sudha, L.'
'Subramanian, K.'
'Senthil Selvan, J.'
'Steiner, Th.'
'Koellner, G.'
'Ramdas, K.'
'Srinivasan, N.'
_publ_contact_author
;
   Dr Thomas Steiner
   Institut für Kristallographie
   Freie Universität Berlin
   Takustrasse 6
   D-14195 Berlin
   Germany
;
_publ_section_title
;
 3,3-(Oxydiethyl)-1,2-di(o-methylphenyl)guanidinium Chloride
 Monohydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              3238
_journal_page_last               3240
_journal_paper_doi               10.1107/S0108270196011274
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C19 H24 N3 O +, Cl -, H2O'
_chemical_formula_sum            'C19 H26 Cl N3 O2'
_chemical_formula_weight         363.88
_chemical_name_systematic
;
 1,2-di(o-methyl-phenyl)-3,3-(oxydiethyl)-guanidine hydrochloride
 monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.58(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.970(2)
_cell_length_b                   14.544(3)
_cell_length_c                   16.502(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.1
_cell_measurement_theta_min      10.9
_cell_volume                     1880.3(8)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  SHELXL93
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius Turbo-CAD4'
_diffrn_measurement_method       'ω-2θ scans'
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54176
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3101
_diffrn_reflns_theta_max         59.87
_diffrn_reflns_theta_min         4.08
_diffrn_standards_decay_%        -1.8
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.934
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   '\y-scan (North, Philips & Matthews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'irregular plate'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.036
_refine_ls_goodness_of_fit_obs   1.058
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_restrained_S_obs      1.059
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_obs          0.0389
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0665P)²+0.8109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1118
_refine_ls_wR_factor_obs         0.1110
_reflns_number_observed          2634
_reflns_number_total             2777
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ta1111.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0665P)^2^+0.8109P] 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^)+(0.0665P)^2^+0.8109P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2005836
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
Cl 1 -0.20585(6) 0.40458(3) 0.22177(3) 0.0477(2) Uani d . Cl
OW 1 -0.8067(3) 0.0806(2) 0.15756(15) 0.0970(7) Uani d . O
H1W 1 -0.7948(59) 0.0251(22) 0.1954(24) 0.097(14) Uiso d . H
H2W 1 -0.6851(65) 0.0874(30) 0.1383(29) 0.094(14) Uiso d . H
C1 1 0.1611(2) 0.10681(12) 0.43939(11) 0.0343(4) Uani d . C
C2 1 0.3355(2) 0.09739(13) 0.46417(12) 0.0405(5) Uani d . C
H2 1 0.4082(2) 0.08156(13) 0.42278(12) 0.049 Uiso calc R H
C3 1 0.4101(3) 0.10979(14) 0.54607(13) 0.0474(5) Uani d . C
H3 1 0.5362(3) 0.10248(14) 0.56412(13) 0.057 Uiso calc R H
C4 1 0.3093(3) 0.13221(15) 0.60227(13) 0.0505(5) Uani d . C
H4 1 0.3626(3) 0.14269(15) 0.66127(13) 0.061 Uiso calc R H
C5 1 0.1351(3) 0.14036(15) 0.57790(13) 0.0494(5) Uani d . C
H5 1 0.0639(3) 0.15637(15) 0.61986(13) 0.059 Uiso calc R H
C6 1 0.0555(2) 0.12683(13) 0.49611(12) 0.0392(4) Uani d . C
C7 1 -0.1359(3) 0.1292(2) 0.4723(2) 0.0564(6) Uani d . C
H7A 1 -0.1779(3) 0.0688(4) 0.4475(10) 0.085 Uiso calc R H
H7B 1 -0.1704(3) 0.1794(8) 0.4311(8) 0.085 Uiso calc R H
H7C 1 -0.1868(3) 0.1411(12) 0.5223(2) 0.085 Uiso calc R H
C1' 1 0.1860(2) 0.28189(12) 0.35144(11) 0.0375(4) Uani d . C
C2' 1 0.3306(3) 0.25924(15) 0.32004(12) 0.0470(5) Uani d . C
H2' 1 0.3222(3) 0.21555(15) 0.27268(12) 0.056 Uiso calc R H
C3' 1 0.4869(3) 0.2974(2) 0.35457(15) 0.0599(6) Uani d . C
H3' 1 0.5922(3) 0.2809(2) 0.33290(15) 0.072 Uiso calc R H
C4' 1 0.4951(3) 0.3584(2) 0.41926(15) 0.0644(7) Uani d . C
H4' 1 0.6074(3) 0.3860(2) 0.44461(15) 0.077 Uiso calc R H
C5' 1 0.3510(3) 0.3817(2) 0.44923(14) 0.0576(6) Uani d . C
H5' 1 0.3603(3) 0.4264(2) 0.49586(14) 0.069 Uiso calc R H
C6' 1 0.1914(3) 0.34412(14) 0.41591(12) 0.0444(5) Uani d . C
C7' 1 0.0354(3) 0.3708(2) 0.4490(2) 0.0620(6) Uani d . C
H7'1 1 0.0683(5) 0.4136(10) 0.4967(7) 0.093 Uiso calc R H
H7'2 1 -0.0187(13) 0.3145(2) 0.4676(10) 0.093 Uiso calc R H
H7'3 1 -0.0474(10) 0.4022(11) 0.4047(4) 0.093 Uiso calc R H
N8 1 0.0888(2) 0.09009(10) 0.35461(9) 0.0374(4) Uani d . N
HN8 1 0.1056(2) 0.02896(10) 0.33244(9) 0.065(7) Uiso calc R H
C9 1 0.0001(2) 0.15129(12) 0.30336(10) 0.0341(4) Uani d . C
N10 1 0.0250(2) 0.24154(10) 0.31425(9) 0.0380(4) Uani d . N
HN10 1 -0.0718(2) 0.28276(10) 0.29591(9) 0.074(8) Uiso calc R H
N11 1 -0.1186(2) 0.12048(11) 0.24147(10) 0.0397(4) Uani d . N
C12 1 -0.1773(3) 0.17032(15) 0.16410(11) 0.0439(5) Uani d . C
H12A 1 -0.1421(3) 0.13638(15) 0.11726(11) 0.053 Uiso calc R H
H12B 1 -0.1242(3) 0.23281(15) 0.16730(11) 0.053 Uiso calc R H
C13 1 -0.3680(3) 0.17906(15) 0.14953(13) 0.0502(5) Uani d . C
H13A 1 -0.4019(3) 0.21789(15) 0.19386(13) 0.060 Uiso calc R H
H13B 1 -0.4085(3) 0.21027(15) 0.09548(13) 0.060 Uiso calc R H
O14 1 -0.4469(2) 0.09091(11) 0.14906(10) 0.0605(5) Uani d . O
C15 1 -0.3906(3) 0.0445(2) 0.22549(15) 0.0575(6) Uani d . C
H15A 1 -0.4488(3) -0.0165(2) 0.22415(15) 0.069 Uiso calc R H
H15B 1 -0.4234(3) 0.0814(2) 0.27129(15) 0.069 Uiso calc R H
C16 1 -0.2006(3) 0.03039(14) 0.24207(13) 0.0474(5) Uani d . C
H16A 1 -0.1638(3) 0.00011(14) 0.29686(13) 0.057 Uiso calc R H
H16B 1 -0.1670(3) -0.01004(14) 0.19869(13) 0.057 Uiso calc R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
H1W OW H2W 106.(4) ?
C2 C1 C6 121.2(2) ?
C2 C1 N8 118.3(2) ?
C6 C1 N8 120.3(2) ?
C1 C2 C3 120.3(2) ?
C1 C2 H2 119.87(12) ?
C3 C2 H2 119.87(13) ?
C4 C3 C2 119.4(2) ?
C4 C3 H3 120.30(12) ?
C2 C3 H3 120.30(13) ?
C3 C4 C5 120.4(2) ?
C3 C4 H4 119.79(12) ?
C5 C4 H4 119.79(13) ?
C4 C5 C6 121.7(2) ?
C4 C5 H5 119.17(13) ?
C6 C5 H5 119.17(12) ?
C5 C6 C1 117.0(2) ?
C5 C6 C7 120.6(2) ?
C1 C6 C7 122.4(2) ?
C6 C7 H7A 109.47(12) ?
C6 C7 H7B 109.47(12) ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.47(13) ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C2' C1' C6' 121.9(2) ?
C2' C1' N10 118.7(2) ?
C6' C1' N10 119.4(2) ?
C3' C2' C1' 119.8(2) ?
C3' C2' H2' 120.11(15) ?
C1' C2' H2' 120.11(12) ?
C4' C3' C2' 119.1(2) ?
C4' C3' H3' 120.45(14) ?
C2' C3' H3' 120.45(14) ?
C5' C4' C3' 120.8(2) ?
C5' C4' H4' 119.58(14) ?
C3' C4' H4' 119.58(14) ?
C4' C5' C6' 121.4(2) ?
C4' C5' H5' 119.28(14) ?
C6' C5' H5' 119.28(14) ?
C1' C6' C5' 116.9(2) ?
C1' C6' C7' 122.4(2) ?
C5' C6' C7' 120.7(2) ?
C6' C7' H7'1 109.47(13) ?
C6' C7' H7'2 109.47(13) ?
H7'1 C7' H7'2 109.5 ?
C6' C7' H7'3 109.47(12) ?
H7'1 C7' H7'3 109.5 ?
H7'2 C7' H7'3 109.5 ?
C9 N8 C1 125.2(2) yes
C9 N8 HN8 117.42(10) ?
C1 N8 HN8 117.42(9) ?
N10 C9 N11 120.0(2) yes
N10 C9 N8 121.4(2) yes
N11 C9 N8 118.6(2) yes
C9 N10 C1' 123.8(2) yes
C9 N10 HN10 118.10(10) ?
C1' N10 HN10 118.10(10) ?
C9 N11 C16 123.3(2) yes
C9 N11 C12 124.6(2) yes
C16 N11 C12 112.1(2) yes
N11 C12 C13 109.5(2) ?
N11 C12 H12A 109.78(11) ?
C13 C12 H12A 109.78(12) ?
N11 C12 H12B 109.78(11) ?
C13 C12 H12B 109.78(12) ?
H12A C12 H12B 108.2 ?
O14 C13 C12 110.9(2) ?
O14 C13 H13A 109.45(12) ?
C12 C13 H13A 109.45(12) ?
O14 C13 H13B 109.45(11) ?
C12 C13 H13B 109.45(12) ?
H13A C13 H13B 108.0 ?
C13 O14 C15 110.7(2) yes
O14 C15 C16 111.6(2) ?
O14 C15 H15A 109.30(11) ?
C16 C15 H15A 109.30(11) ?
O14 C15 H15B 109.30(13) ?
C16 C15 H15B 109.30(13) ?
H15A C15 H15B 108.0 ?
N11 C16 C15 108.2(2) ?
N11 C16 H16A 110.06(10) ?
C15 C16 H16A 110.06(13) ?
N11 C16 H16B 110.06(12) ?
C15 C16 H16B 110.06(13) ?
H16A C16 H16B 108.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
OW H1W 1.01(2) ?
OW H2W 1.08(5) ?
C1 C2 1.382(3) ?
C1 C6 1.399(3) ?
C1 N8 1.433(2) yes
C2 C3 1.385(3) ?
C2 H2 1.00 ?
C3 C4 1.373(3) ?
C3 H3 1.00 ?
C4 C5 1.377(3) ?
C4 H4 1.00 ?
C5 C6 1.396(3) ?
C5 H5 1.00 ?
C6 C7 1.505(3) ?
C7 H7A 1.00 ?
C7 H7B 1.00 ?
C7 H7C 1.00 ?
C1' C2' 1.388(3) ?
C1' C6' 1.391(3) ?
C1' N10 1.442(2) yes
C2' C3' 1.387(3) ?
C2' H2' 1.00 ?
C3' C4' 1.381(4) ?
C3' H3' 1.00 ?
C4' C5' 1.374(4) ?
C4' H4' 1.00 ?
C5' C6' 1.401(3) ?
C5' H5' 1.00 ?
C6' C7' 1.498(3) ?
C7' H7'1 1.00 ?
C7' H7'2 1.00 ?
C7' H7'3 1.00 ?
N8 C9 1.337(2) yes
N8 HN8 0.98 ?
C9 N10 1.335(2) yes
C9 N11 1.335(2) yes
N10 HN10 0.98 ?
N11 C16 1.465(3) yes
N11 C12 1.468(2) yes
C12 C13 1.499(3) ?
C12 H12A 1.00 ?
C12 H12B 1.00 ?
C13 O14 1.427(3) ?
C13 H13A 1.00 ?
C13 H13B 1.00 ?
O14 C15 1.428(3) ?
C15 C16 1.503(3) ?
C15 H15A 1.00 ?
C15 H15B 1.00 ?
C16 H16A 1.00 ?
C16 H16B 1.00 ?
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
C1 N8 C9 N10 27.0(3) yes
C2 C1 N8 C9 -120.6(2) yes
C1 N8 C9 N11 -151.3(2) yes
N11 C9 N10 C1' -151.8(2) yes
N8 C9 N10 C1' 30.0(3) yes
C2' C1' N10 C9 53.1(2) yes
N10 C9 N11 C16 -155.7(2) yes
N8 C9 N11 C16 22.6(3) yes
N10 C9 N11 C12 26.9(3) yes
N8 C9 N11 C12 -154.9(2) yes
C9 N11 C12 C13 -126.3(2) yes
C9 N11 C16 C15 126.3(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21137919
