#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/40/2004059.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_2004059
loop_
_publ_author_name
'Aubry, A.'
'Brembilla, A.'
'Faivre, V.'
'Lochon, P.'
_publ_section_title
;
 2-Hydroxymethyl-1-pentylbenzimidazole Hemi(1,4-dioxane) Solvate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2147
_journal_page_last               2148
_journal_paper_doi               10.1107/S0108270195006688
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'see prep'
_chemical_formula_moiety         'C13 H18 N2 O, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C15 H22 N2 O2'
_chemical_formula_weight         262.35
_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'
_atom_type_scat_source           SHELX90
_cell_angle_alpha                90
_cell_angle_beta                 101.08(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.801(1)
_cell_length_b                   7.819(1)
_cell_length_c                   15.169(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     1490.0(3)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2834
_diffrn_reflns_theta_max         70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.17
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.29
_refine_diff_density_min         0.22
_refine_ls_extinction_coef       0.032
_refine_ls_extinction_method     'SHELX90 (Sheldrick, 1990)'
_refine_ls_goodness_of_fit_obs   4.34
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2355
_refine_ls_R_factor_obs          0.044
_refine_ls_shift/esd_max         '0.4 on heavy atoms'
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 25.18/[σ²(F)+0.00004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          2355
_reflns_number_total             2664
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            pa1179.cif
_cod_data_source_block           pa1179a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w =
25.18/[\s^2^(F)+0.00004F^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 25.18/[\s^2^(F)+0.00004F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1490
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2004059
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,1/2-y,1/2+z
-x,-y,-z
-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_B_iso_or_equiv
N(1) -.0565(1) .2249(2) -.0425(9) 3.87(3)
N(2) .0790(1) .3866(2) -.0682(9) 3.67(3)
O(1) .1805(1) .0730(2) .0465(9) 5.06(3)
C(1) -.0036(1) .4119(2) -.1405(1) 3.67(4)
C(2) -.0116(2) .5099(2) -.2181(1) 4.67(4)
C(3) -.1069(2) .5027(3) -.2777(1) 5.28(5)
C(4) -.1919(2) .4054(3) -.2609(1) 5.25(5)
C(5) -.1839(1) .3089(3) -.1838(1) 4.64(5)
C(6) -.0875(1) .3113(2) -.1234(1) 3.67(4)
C(7) .0428(1) .2722(2) -.0125(1) 3.69(4)
C(8) .1113(2) .1994(3) .0699(1) 4.60(5)
C(9) .1848(1) .4643(3) -.0582(1) 4.27(4)
C(10) .2504(1) .3853(3) -.1210(1) 4.44(4)
C(11) .3559(2) .4747(3) -.1172(1) 4.52(5)
C(12) .4182(2) .4041(4) -.1841(2) 5.69(6)
C(13) .5244(2) .4886(5) -.1804(2) 7.54(9)
O(2) .5539(1) .4411(2) -.4166(9) 7.42(5)
C(14) .4033(2) .5830(4) -.5045(2) 6.73(7)
C(15) .4411(2) .4448(5) -.4396(2) 7.45(8)
H(O1) .1370(2) -.0380(3) .0340(1) 7.9(6)
H21 0.048(2) 0.580(3) -0.230(1) 6.0(5)
H31 -0.119(1) 0.569(3) -0.333(1) 6.2(5)
H41 -0.258(2) 0.409(2) -0.303(1) 5.8(5)
H51 -0.241(1) 0.240(2) -0.169(1) 5.3(4)
H81 0.158(2) 0.292(3) 0.103(1) 6.8(5)
H82 0.062(1) 0.150(2) 0.109(1) 5.3(4)
H91 0.221(1) 0.453(2) 0.004(1) 5.1(4)
H92 0.173(1) 0.587(3) -0.070(1) 5.9(5)
H101 0.260(1) 0.261(3) -0.107(1) 5.8(5)
H102 0.206(1) 0.393(2) -0.185(1) 5.0(4)
H111 0.343(1) 0.603(3) -0.127(1) 6.5(5)
H112 0.400(1) 0.471(2) -0.052(1) 5.9(4)
H121 0.371(2) 0.408(3) -0.242(1) 6.8(5)
H122 0.420(2) 0.277(3) -0.185(1) 8.3(6)
H131 0.563(2) 0.450(3) -0.228(2) 9.0(6)
H132 0.566(2) 0.478(3) -0.120(2) 8.3(6)
H133 0.506(2) 0.617(4) -0.198(2) 13.2(8)
H141 0.328(2) 0.580(3) -0.522(1) 6.3(5)
H142 0.463(2) 0.690(4) -0.495(2) 10.1(7)
H151 0.423(2) 0.484(3) -0.382(2) 10.2(6)
H152 0.419(2) 0.338(4) -0.467(2) 13(1)
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
C(6) N(1) C(7) 105.20(10) yes
C(1) N(2) C(7) 106.50(10) yes
C(1) N(2) C(9) 125.00(10) yes
C(7) N(2) C(9) 128.40(10) yes
C(2) C(1) C(6) 122.20(10) yes
C(2) C(1) N(2) 132.1(2) yes
C(6) C(1) N(2) 105.70(10) yes
C(1) C(2) C(3) 116.5(2) yes
C(2) C(3) C(4) 122.00(10) yes
C(3) C(4) C(5) 121.4(2) yes
C(4) C(5) C(6) 117.6(2) yes
C(1) C(6) C(5) 120.3(2) yes
C(1) C(6) N(1) 109.80(10) yes
C(5) C(6) N(1) 130.0(2) yes
C(8) C(7) N(2) 123.40(10) yes
C(7) C(8) O(1) 110.50(10) yes
C(9) C(10) C(11) 112.7(2) yes
C(10) C(11) C(12) 112.7(2) yes
C(11) C(12) C(13) 113.9(2) yes
N(1) C(7) C(8) 123.6(2) yes
N(1) C(7) N(2) 112.9(2) yes
N(2) C(9) C(10) 112.3(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(7) 1.318(2) yes
N(2) C(9) 1.466(2) yes
C(1) C(2) 1.392(2) yes
C(1) C(6) 1.395(2) yes
C(1) N(2) 1.383(2) yes
C(2) C(3) 1.373(3) yes
C(3) C(4) 1.391(3) yes
C(4) C(5) 1.388(2) yes
C(5) C(6) 1.391(2) yes
C(6) N(1) 1.391(2) yes
C(7) C(8) 1.495(2) yes
C(7) N(2) 1.371(2) yes
C(8) O(1) 1.418(3) yes
C(9) C(10) 1.516(3) yes
C(10) C(11) 1.511(3) yes
C(11) C(12) 1.512(3) yes
C(12) C(13) 1.503(4) 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
N(2) C(7) C(8) O(1) -75.7(2) yes
C(7) N(2) C(9) C(10) 104.3(2) yes
N(2) C(9) C(10) C(11) 175.0(2) yes
C(9) C(10) C(11) C(12) -176.1(2) yes
C(10) C(11) C(12) C(13) -178.9(3) yes
