#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/45/2004516.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_2004516
loop_
_publ_author_name
'Ravikumar, K.'
'Mohan, K. C.'
'Roy, S.'
'Singh, A. K.'
_publ_section_title
;
 A Key Intermediate in the Synthesis of Pentamidine:
 4,4'-[1,5-Pentanediylbis(oxy)]bisbenzonitrile
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              403
_journal_page_last               405
_journal_paper_doi               10.1107/S0108270195011966
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.36
_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           'SHELXTL-Plus (Sheldrick, 1991)'
_cell_angle_alpha                90.
_cell_angle_beta                 96.95(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   9.163(1)
_cell_length_b                   8.370(1)
_cell_length_c                   21.786(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      17
_cell_measurement_theta_min      8
_cell_volume                     1658.6(4)
_computing_cell_refinement       'P3 Diffractometer Program'
_computing_data_collection       'P3 Diffractometer Program (Siemens, 1991)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1991)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    SHELXTL-Plus
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.010
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2590
_diffrn_reflns_theta_max         22.5
_diffrn_standards_decay_%        <=1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.93
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1573
_refine_ls_R_factor_obs          0.043
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0061F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          1573
_reflns_number_total             2533
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            kh1052.cif
_cod_data_source_block           kh1052a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0061F^2^]'
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^(F) +
0.0061F^2^]'.

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               2004516
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_U_iso_or_equiv
O(1) 1.4197(2) -0.0782(2) 0.1505(1) 0.073(1)
O(2) 0.6678(2) 0.1798(2) 0.0455(1) 0.064(1)
N(1) 2.1123(3) -0.0548(3) 0.2912(1) 0.096(1)
N(2) 0.0558(3) 0.6102(3) 0.0668(1) 0.090(1)
C(1) 1.8416(3) -0.0571(3) 0.2409(1) 0.068(1)
C(2) 1.8009(3) -0.1687(2) 0.1943(2) 0.076(1)
C(3) 1.6591(3) -0.1710(3) 0.1656(1) 0.072(1)
C(4) 1.5557(3) -0.0638(3) 0.1819(1) 0.060(1)
C(5) 1.5964(3) 0.0494(4) 0.2274(1) 0.071(1)
C(6) 1.7387(3) 0.0515(4) 0.2572(1) 0.075(1)
C(7) 1.3105(3) 0.0399(3) 0.1592(1) 0.061(1)
C(8) 1.1761(3) 0.0033(3) 0.1152(1) 0.062(1)
C(9) 1.0548(2) 0.1247(3) 0.1198(1) 0.055(1)
C(10) 0.9181(3) 0.0979(3) 0.0743(1) 0.061(1)
C(11) 0.7992(2) 0.2140(3) 0.0864(1) 0.058(1)
C(12) 0.5476(3) 0.2724(3) 0.0513(1) 0.052(1)
C(13) 0.4211(3) 0.2345(3) 0.0124(1) 0.063(1)
C(14) 0.2943(3) 0.3209(3) 0.0146(1) 0.063(1)
C(15) 0.2922(3) 0.4479(3) 0.0560(1) 0.053(1)
C(16) 0.4190(3) 0.4845(3) 0.0948(1) 0.063(1)
C(17) 0.5463(3) 0.3983(3) 0.0929(1) 0.060(1)
C(18) 0.1606(3) 0.5386(3) 0.0607(1) 0.065(1)
C(19) 1.9921(3) -0.0549(4) 0.2698(1) 0.078(1)
H(2) 1.8725(3) -0.2429(3) 0.1826(1) ?
H(3) 1.6301(3) -0.2475(3) 0.1336(1) ?
H(5) 1.5259(3) 0.1273(4) 0.2372(1) ?
H(6) 1.7652(3) 0.1254(4) 0.2904(1) ?
H(7A) 1.3462(3) 0.1446(3) 0.1510(1) ?
H(7B) 1.2864(3) 0.0365(3) 0.2008(1) ?
H(8A) 1.1410(2) -0.1014(3) 0.1239(1) ?
H(8B) 1.2021(2) 0.0038(3) 0.0739(1) ?
H(9A) 1.0928(2) 0.2295(3) 0.1134(1) ?
H(9B) 1.0271(2) 0.1206(3) 0.1609(1) ?
H(10A) 0.8839(3) -0.0097(3) 0.0778(1) ?
H(10B) 0.9417(3) 0.1138(3) 0.0330(1) ?
H(11A) 0.7803(2) 0.2029(3) 0.1286(1) ?
H(11B) 0.8308(2) 0.3215(3) 0.0802(1) ?
H(13) 0.4226(3) 0.1477(3) -0.0164(1) ?
H(14) 0.2067(3) 0.2958(3) -0.0125(1) ?
H(16) 0.4173(3) 0.5731(3) 0.1228(1) ?
H(17) 0.6332(3) 0.4243(3) 0.1202(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(4) O(1) C(7) 119.1(2) yes
C(2) C(1) C(6) 119.6(2) yes
C(6) C(1) C(19) 121.6(3) yes
O(1) C(4) C(5) 125.0(2) yes
C(7) C(8) C(9) 111.9(2) yes
C(9) C(10) C(11) 110.3(2) yes
O(2) C(12) C(13) 115.9(2) yes
C(14) C(15) C(16) 119.1(2) yes
C(16) C(15) C(18) 119.2(2) yes
N(1) C(19) C(1) 178.1(3) yes
C(11) O(2) C(12) 117.0(2) yes
C(2) C(1) C(19) 118.8(3) yes
O(1) C(4) C(3) 115.4(2) yes
O(1) C(7) C(8) 107.9(2) yes
C(8) C(9) C(10) 114.3(2) yes
O(2) C(11) C(10) 109.4(2) yes
O(2) C(12) C(17) 124.2(2) yes
C(14) C(15) C(18) 121.6(2) yes
N(2) C(18) C(15) 177.4(3) yes
C(2) C(3) C(4) 120.9(3) no
C(4) C(5) C(6) 119.9(3) no
C(12) C(13) C(14) 120.3(2) no
C(12) C(17) C(16) 119.4(2) no
C(1) C(2) C(3) 119.7(3) no
C(3) C(4) C(5) 119.6(2) no
C(1) C(6) C(5) 120.2(3) no
C(13) C(12) C(17) 120.0(2) no
C(13) C(14) C(15) 120.1(2) no
C(15) C(16) C(17) 121.1(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(4) 1.354(3) yes
O(2) C(11) 1.437(3) yes
N(1) C(19) 1.143(4) yes
C(1) C(19) 1.445(4) yes
C(8) C(9) 1.518(3) yes
C(10) C(11) 1.507(4) yes
O(1) C(7) 1.435(3) yes
O(2) C(12) 1.366(3) yes
N(2) C(18) 1.152(4) yes
C(7) C(8) 1.497(3) yes
C(9) C(10) 1.517(3) yes
C(15) C(18) 1.440(4) yes
C(1) C(2) 1.398(4) no
C(3) C(4) 1.383(4) no
C(5) C(6) 1.385(4) no
C(12) C(17) 1.391(4) no
C(14) C(15) 1.396(4) no
C(1) C(6) 1.386(4) no
C(2) C(3) 1.372(4) no
C(4) C(5) 1.388(4) no
C(12) C(13) 1.388(3) no
C(13) C(14) 1.375(4) no
C(15) C(16) 1.386(3) no
C(16) C(17) 1.377(4) no
