#------------------------------------------------------------------------------
#$Date: 2019-06-20 14:41:52 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/16/1551684.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1551684
loop_
_publ_author_name
'MARFO-OWUSU, Emmanuel'
'YABUUCHI, Kazuhiro'
'KATO, Takashi'
'WATKIN, David J.'
_publ_section_title
;
 Crystal Structure of a Short Alkyl Chain Pyridine-Based Bisurea Compound:
 The Effects of Alkyl Chain Length in a Supramolecule Module
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              49
_journal_paper_doi               10.2116/xraystruct.29.49
_journal_volume                  29
_journal_year                    2013
_chemical_formula_moiety         'C11 H17 N5 O2'
_chemical_formula_sum            'C11 H17 N5 O2'
_chemical_formula_weight         251.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 93.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6800(5)
_cell_length_b                   8.1730(5)
_cell_length_c                   12.9490(9)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    298
_cell_measurement_theta_max      25
_cell_measurement_theta_min      0
_cell_volume                     1339.30(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'Xpress Data collection (MAC Science, 1989)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius DIP2000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2579
_diffrn_reflns_theta_full        25.435
_diffrn_reflns_theta_max         26.833
_diffrn_reflns_theta_min         2.949
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.19
_refine_ls_extinction_coef       600(120)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9447
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.0037260
_refine_ls_shift/su_mean         0.0003261
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;

 Method= Modified Sheldrick 

 w=1/[σ²(F²) + ( 0.12P)² + 0.29P] 

 ,where P=(max(Fo²,0) + 2Fc²)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1798
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1794
_reflns_limit_h_max              16
_reflns_limit_h_min              -15
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              0
_reflns_limit_l_min              -14
_reflns_number_gt                2096
_reflns_number_total             2579
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   4.97
_oxford_diffrn_Wilson_scale      1.10
_oxford_refine_ls_r_factor_ref   0.0668
_oxford_refine_ls_scale          1.024(10)
_oxford_reflns_number_all        2571
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            29_49_1.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               1551684
_iucr_refine_instructions_details_constraints
;

#

# Punched on 03/10/13 at 03:05:09

#

#LIST     12                                                                    

BLOCK 

CONT SCALE 

CONT O    (    1 ,X'S,U'S)  UNTIL C    (   18 ) 

CONT H    (   42 ,X'S)  UNTIL H    (  181 ) 

CONT EXTPARAM 

RIDE N   (   3,X'S) H   (  31,X'S) 

RIDE N   (   6,X'S) H   (  61,X'S) 

RIDE N   (  10,X'S) H   ( 101,X'S) 

RIDE N   (  13,X'S) H   ( 131,X'S) 

END                                                                             

;
_iucr_refine_instructions_details_restraints
;

#

# Punched on 03/10/13 at 03:05:09

#

#LIST     16                                                                    

NO 

REM   HREST   START (DO NOT REMOVE THIS LINE) 

REM NO H   NO #H U MULT DIST 

REM C-H 

REM >4           1.5    .96 DISORDER 

REM 1      1     1.2    .93 C C-H (ACETYLENE) 

REM 1      2     1.2    .93 C-C(H)-C 

REM 1      3     1.2    .98 (C)3-C-H 

REM 2      1     1.2    .93 C=C-H(2) 

REM 2      2     1.2    .97 (C)2-C-(H)2 

REM 3      1     1.5    .96 C-C-(H)3 

REM N-H 

REM >4           1.5    .89 DISORDER 

REM 1      1     1.2    .86 N-N/H 

REM 1      2     1.2    .86 (C)2-N-H 

REM 1      3     1.2    .89 (C)3-N-H 

REM 2      1     1.2    .86 C-N-(H)2 

REM 2      2     1.2    .89 (C)2-N-(H)2 

REM 3      1     1.2    .89 C-H-(H)3 

REM O-H 

REM 1      1     1.5    .82 O-H 

REM 

REM DIST      ESD = 0.02 

REM VIB       ESD = 0.002 

REM ANGLE     ESD = 2.0 

REM            H1-N-R2 

DIST 0.86, 0.02 = 

CONT N ( 3) TO H(31) 

REST 0.087, 0.002 = H(31,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(31) TO N ( 3) TO C(2) 

CONT H(31) TO N ( 3) TO C(4) 

REM            2 H ON SP 3 

DIST 0.97, 0.02 = 

CONT C ( 4) TO H(42) 

CONT C ( 4) TO H(41) 

REST 0.105, 0.002 = H(42,U[ISO]) 

REST 0.105, 0.002 = H(41,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(42) TO C ( 4) TO N(3) 

CONT H(42) TO C ( 4) TO C(5) 

CONT H(41) TO C ( 4) TO N(3) 

CONT H(41) TO C ( 4) TO C(5) 

ANGLE 109.54, 2.0 = 

CONT H(42) TO C ( 4) TO H(41) 

REM            3 H ON SP 3 

DIST 0.96, 0.02 = 

CONT C ( 5) TO H(52) 

CONT C ( 5) TO H(51) 

CONT C ( 5) TO H(53) 

REST 0.245, 0.002 = H(52,U[ISO]) 

REST 0.245, 0.002 = H(51,U[ISO]) 

REST 0.245, 0.002 = H(53,U[ISO]) 

ANGLE 109.54, 2.0 = 

CONT C(4) TO C ( 5) TO H(52) 

CONT C(4) TO C ( 5) TO H(51) 

CONT C(4) TO C ( 5) TO H(53) 

ANGLE 0.0, 2.0 = MEAN H(52) TO C ( 5) TO H(51) 

CONT H(52) TO C ( 5) TO H(53) 

CONT H(51) TO C ( 5) TO H(53) 

REM            H1-N-R2 

DIST 0.86, 0.02 = 

CONT N ( 6) TO H(61) 

REST 0.081, 0.002 = H(61,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(61) TO N ( 6) TO C(2) 

CONT H(61) TO N ( 6) TO C(7) 

REM            H1-N-R2 

DIST 0.86, 0.02 = 

CONT N ( 10) TO H(101) 

REST 0.072, 0.002 = H(101,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(101) TO N ( 10) TO C(9) 

CONT H(101) TO N ( 10) TO C(11) 

REM            H1-N-R2 

DIST 0.86, 0.02 = 

CONT N ( 13) TO H(131) 

REST 0.094, 0.002 = H(131,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(131) TO N ( 13) TO C(11) 

CONT H(131) TO N ( 13) TO C(14) 

REM            2 H ON SP 3 

DIST 0.97, 0.02 = 

CONT C ( 14) TO H(141) 

CONT C ( 14) TO H(142) 

REST 0.102, 0.002 = H(141,U[ISO]) 

REST 0.102, 0.002 = H(142,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(141) TO C ( 14) TO N(13) 

CONT H(141) TO C ( 14) TO C(15) 

CONT H(142) TO C ( 14) TO N(13) 

CONT H(142) TO C ( 14) TO C(15) 

ANGLE 109.54, 2.0 = 

CONT H(141) TO C ( 14) TO H(142) 

REM            3 H ON SP 3 

DIST 0.96, 0.02 = 

CONT C ( 15) TO H(151) 

CONT C ( 15) TO H(152) 

CONT C ( 15) TO H(153) 

REST 0.142, 0.002 = H(151,U[ISO]) 

REST 0.142, 0.002 = H(152,U[ISO]) 

REST 0.142, 0.002 = H(153,U[ISO]) 

ANGLE 109.54, 2.0 = 

CONT C(14) TO C ( 15) TO H(151) 

CONT C(14) TO C ( 15) TO H(152) 

CONT C(14) TO C ( 15) TO H(153) 

ANGLE 0.0, 2.0 = MEAN H(151) TO C ( 15) TO H(152) 

CONT H(151) TO C ( 15) TO H(153) 

CONT H(152) TO C ( 15) TO H(153) 

REM            1 H ON SP 2 

DIST 0.93, 0.02 = 

CONT C ( 16) TO H(161) 

REST 0.082, 0.002 = H(161,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(161) TO C ( 16) TO C(9) 

CONT H(161) TO C ( 16) TO C(17) 

PLANAR C ( 16) C(9) C(17) H(161) 

REM            1 H ON SP 2 

DIST 0.93, 0.02 = 

CONT C ( 17) TO H(171) 

REST 0.089, 0.002 = H(171,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(171) TO C ( 17) TO C(16) 

CONT H(171) TO C ( 17) TO C(18) 

PLANAR C ( 17) C(16) C(18) H(171) 

REM            1 H ON SP 2 

DIST 0.93, 0.02 = 

CONT C ( 18) TO H(181) 

REST 0.082, 0.002 = H(181,U[ISO]) 

ANGLE 0.0, 2.0 = MEAN 

CONT H(181) TO C ( 18) TO C(7) 

CONT H(181) TO C ( 18) TO C(17) 

PLANAR C ( 18) C(7) C(17) H(181) 

REM   HREST   END (DO NOT REMOVE THIS LINE) 

END                                                                             

;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.51736(10) 0.5919(2) 0.12584(12) 0.0795 1.0000 Uani .
C2 C 0.42666(14) 0.5510(2) 0.13733(16) 0.0621 1.0000 Uani D
N3 N 0.37993(12) 0.5757(2) 0.22637(14) 0.0727 1.0000 Uani D
C4 C 0.43268(18) 0.6524(4) 0.31864(19) 0.0873 1.0000 Uani D
C5 C 0.3770(4) 0.6277(7) 0.4122(3) 0.1648 1.0000 Uani D
N6 N 0.37183(12) 0.4747(2) 0.05458(13) 0.0672 1.0000 Uani D
C7 C 0.27086(13) 0.4171(2) 0.04463(14) 0.0563 1.0000 Uani D
N8 N 0.20671(10) 0.45151(18) 0.12018(12) 0.0550 1.0000 Uani .
C9 C 0.10909(13) 0.3964(2) 0.10883(14) 0.0544 1.0000 Uani D
N10 N 0.04948(11) 0.4474(2) 0.19197(13) 0.0598 1.0000 Uani D
C11 C -0.03796(13) 0.3753(2) 0.22528(16) 0.0611 1.0000 Uani D
O12 O -0.07328(10) 0.24611(18) 0.18727(12) 0.0738 1.0000 Uani .
N13 N -0.07885(13) 0.4559(2) 0.30600(17) 0.0783 1.0000 Uani D
C14 C -0.17032(17) 0.4001(3) 0.3580(2) 0.0846 1.0000 Uani D
C15 C -0.2653(2) 0.4881(4) 0.3205(3) 0.0946 1.0000 Uani D
C16 C 0.07147(15) 0.3043(3) 0.02358(16) 0.0681 1.0000 Uani D
C17 C 0.14012(17) 0.2692(3) -0.05308(16) 0.0746 1.0000 Uani D
C18 C 0.24056(15) 0.3246(3) -0.04404(16) 0.0679 1.0000 Uani D
H42 H 0.4434(17) 0.764(2) 0.3070(15) 0.1076 1.0000 Uiso D
H41 H 0.4974(14) 0.595(2) 0.3346(15) 0.1073 1.0000 Uiso D
H52 H 0.407(3) 0.694(5) 0.468(2) 0.2519 1.0000 Uiso D
H51 H 0.3025(17) 0.648(5) 0.402(2) 0.2529 1.0000 Uiso D
H53 H 0.391(3) 0.513(3) 0.428(3) 0.2523 1.0000 Uiso D
H141 H -0.1629(15) 0.413(3) 0.4347(14) 0.1085 1.0000 Uiso D
H142 H -0.1821(16) 0.282(2) 0.3434(17) 0.1080 1.0000 Uiso D
H151 H -0.3233(16) 0.441(3) 0.3559(19) 0.1374 1.0000 Uiso D
H152 H -0.2559(18) 0.604(2) 0.3363(19) 0.1374 1.0000 Uiso D
H153 H -0.2690(19) 0.463(3) 0.2447(15) 0.1376 1.0000 Uiso D
H161 H 0.0027(12) 0.2669(14) 0.0201(11) 0.0770 1.0000 Uiso D
H171 H 0.1145(12) 0.2066(14) -0.1139(12) 0.0839 1.0000 Uiso D
H181 H 0.2878(12) 0.3042(14) -0.0948(11) 0.0761 1.0000 Uiso D
H101 H 0.0722 0.5422 0.2246 0.0682 1.0000 Uiso DR
H61 H 0.4096 0.4550 0.0014 0.0762 1.0000 Uiso DR
H131 H -0.0525 0.5600 0.3252 0.0890 1.0000 Uiso DR
H31 H 0.3111 0.5665 0.2262 0.0822 1.0000 Uiso DR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 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
O1 C2 N3 122.36(18) yes
O1 C2 N6 117.44(17) yes
N3 C2 N6 120.20(16) yes
C2 N3 C4 123.89(17) yes
C2 N3 H31 118.5 no
C4 N3 H31 116.1 no
N3 C4 C5 113.4(2) yes
N3 C4 H42 110.3(12) no
C5 C4 H42 110.7(13) no
N3 C4 H41 107.8(12) no
C5 C4 H41 102.0(13) no
H42 C4 H41 112.4(15) no
C4 C5 H52 110.9(16) no
C4 C5 H51 112.6(16) no
H52 C5 H51 110.6(17) no
C4 C5 H53 102.5(17) no
H52 C5 H53 109.1(18) no
H51 C5 H53 110.8(17) no
C2 N6 C7 130.57(16) yes
C2 N6 H61 114.6 no
C7 N6 H61 114.7 no
N6 C7 N8 117.91(16) yes
N6 C7 C18 117.99(16) yes
N8 C7 C18 124.10(16) yes
C7 N8 C9 117.12(15) yes
N8 C9 N10 110.93(15) yes
N8 C9 C16 123.04(17) yes
N10 C9 C16 126.01(16) yes
C9 N10 C11 127.04(17) yes
C9 N10 H101 115.5 no
C11 N10 H101 117.5 no
N10 C11 O12 121.99(18) yes
N10 C11 N13 113.14(18) yes
O12 C11 N13 124.82(17) yes
C11 N13 C14 123.8(2) yes
C11 N13 H131 119.5 no
C14 N13 H131 116.3 no
N13 C14 C15 111.0(2) yes
N13 C14 H141 113.7(12) no
C15 C14 H141 107.7(12) no
N13 C14 H142 109.4(12) no
C15 C14 H142 107.8(12) no
H141 C14 H142 107.0(15) no
C14 C15 H151 106.3(14) no
C14 C15 H152 108.8(14) no
H151 C15 H152 111.9(15) no
C14 C15 H153 102.3(14) no
H151 C15 H153 113.1(15) no
H152 C15 H153 113.5(15) no
C9 C16 C17 118.53(17) yes
C9 C16 H161 119.5(10) no
C17 C16 H161 122.0(10) no
C16 C17 C18 119.91(19) yes
C16 C17 H171 119.5(10) no
C18 C17 H171 120.6(10) no
C7 C18 C17 117.29(18) yes
C7 C18 H181 121.1(10) no
C17 C18 H181 121.6(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.216(2) yes
C2 N3 1.344(2) yes
C2 N6 1.388(3) yes
N3 C4 1.472(3) yes
N3 H31 0.876 no
C4 C5 1.454(4) yes
C4 H42 0.934(17) no
C4 H41 0.956(17) no
C5 H52 0.964(19) no
C5 H51 0.959(19) no
C5 H53 0.969(19) no
N6 C7 1.363(2) yes
N6 H61 0.878 no
C7 N8 1.341(2) yes
C7 C18 1.408(3) yes
N8 C9 1.317(2) yes
C9 N10 1.416(2) yes
C9 C16 1.395(3) yes
N10 C11 1.350(2) yes
N10 H101 0.920 no
C11 O12 1.237(2) yes
C11 N13 1.365(3) yes
N13 C14 1.450(3) yes
N13 H131 0.942 no
C14 C15 1.459(4) yes
C14 H141 0.997(17) no
C14 H142 0.996(17) no
C15 H151 0.971(18) no
C15 H152 0.976(18) no
C15 H153 1.000(18) no
C16 C17 1.391(3) yes
C16 H161 0.923(15) no
C17 C18 1.350(3) yes
C17 H171 0.978(16) no
C18 H181 0.931(15) 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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N10 H101 O12 4_555 160.93(5) 0.920 2.020 2.905(3) yes
N6 H61 O1 2_665 174.92(6) 0.878 1.977 2.853(3) yes
N13 H131 O12 4_555 147.73(6) 0.942 2.217 3.055(3) yes
N3 H31 N8 . 129.49(6) 0.876 2.072 2.714(3) yes
