Gradual Transition from NH···Pyridyl Hydrogen Bonding to the NH···O Tape Synthon in Pyridyl Ureas
Byrne, Peter; Turner, David R.; Lloyd, Gareth O.; Clarke, Nigel; Steed, Jonathan W.; Crystal Growth & Design 8 (2008) 3335–; doi:10.1021/cg800247f

data_4503663
_publ_section_title
;
 Gradual Transition from NH&#x00B7;&#x00B7;&#x00B7;Pyridyl Hydrogen
 Bonding to the NH&#x00B7;&#x00B7;&#x00B7;O Tape Synthon in Pyridyl Ureas
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_journal_issue                   9
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              3335
_journal_paper_doi               10.1021/cg800247f
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_chemical_name_common            OrthoTUP
_chemical_name_systematic
;
 oTUP
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.646(2)
_cell_length_b                   5.6149(11)
_cell_length_c                   18.685(4)
_cell_measurement_temperature    120(2)
_cell_volume                     1187.7(4)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 0.71
_diffrn_measured_fraction_theta_full 0.335
_diffrn_measured_fraction_theta_max 0.335
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1249
_diffrn_reflns_av_sigmaI/netI    0.2376
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            1107
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.42
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.001(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         914
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.2525
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1678P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2285
_refine_ls_wR_factor_ref         0.3263
_reflns_number_gt                311
_reflns_number_total             914
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800247f_si_001.cif
_cod_data_source_block           C:\Dave\Arms\OrthoTUP\DT2UREA.CIF
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4503663