Crystal Structure of a Short Alkyl Chain Pyridine-Based Bisurea Compound: The Effects of Alkyl Chain Length in a Supramolecule Module
MARFO-OWUSU, Emmanuel; YABUUCHI, Kazuhiro; KATO, Takashi; WATKIN, David J.; X-ray Structure Analysis Online 29 (2013) 49–; doi:10.2116/xraystruct.29.49

data_1551684
_publ_section_title
;
 Crystal Structure of a Short Alkyl Chain Pyridine-Based Bisurea Compound:
 The Effects of Alkyl Chain Length in a Supramolecule Module
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_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       \w
_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/[\s^2^(F^2^) + ( 0.12P)^2^ + 0.29P] 

 ,where P=(max(Fo^2^,0) + 2Fc^2^)/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>2.0\s(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)
_iucr_refine_instructions_details_constraints
;

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
;

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                                                                             

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_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