data_1101010 _journal_name_full 'Journal of Molecular Structure' loop_ _publ_author_name 'Masao Hashimoto' 'Fukue Tajima' 'Kazuo Eda' 'Kimiaki Yamamura' 'Tadashi Okazaki' _chemical_name_common 'n-tridecylurea' _chemical_melting_point 384.6 _chemical_formula_moiety 'C14 H30 N2 O' _chemical_formula_sum 'C14 H30 N2 O' _chemical_formula_weight 242.40 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 23.124(8) _cell_length_b 7.542(2) _cell_length_c 9.299(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.751(7) _cell_angle_gamma 90.00 _cell_volume 1598.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 314(2) _cell_measurement_reflns_used 836 _cell_measurement_theta_min 2.682 _cell_measurement_theta_max 22.530 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.007 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.297791 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'program SADABS ver. 2.03(Sheldrick)' _diffrn_ambient_temperature 314(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8810 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.1519 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3318 _reflns_number_gt 986 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1157P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3318 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2381 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.2057 _refine_ls_wR_factor_gt 0.1585 _refine_ls_goodness_of_fit_ref 0.687 _refine_ls_restrained_S_all 0.687 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H2B H 0.0925(13) -0.307(4) 0.353(3) 0.074(10) Uiso 1 1 d . . . H1A H 0.1210(11) -0.540(3) 0.593(3) 0.052(8) Uiso 1 1 d . . . H4B H 0.1550(12) -0.019(4) 0.386(3) 0.060(10) Uiso 1 1 d . . . H11A H 0.420(2) 0.888(6) 0.732(4) 0.127(19) Uiso 1 1 d . . . H2A H 0.1558(13) -0.394(4) 0.386(3) 0.074(11) Uiso 1 1 d . . . H9B H 0.2978(14) 0.712(5) 0.683(3) 0.089(12) Uiso 1 1 d . . . H9A H 0.3569(14) 0.597(5) 0.704(3) 0.084(12) Uiso 1 1 d . . . H1B H 0.0622(13) -0.442(4) 0.549(3) 0.063(10) Uiso 1 1 d . . . H7B H 0.2379(13) 0.414(4) 0.649(3) 0.069(10) Uiso 1 1 d . . . H4A H 0.2112(14) -0.105(4) 0.415(3) 0.085(13) Uiso 1 1 d . . . H7A H 0.2964(15) 0.319(5) 0.681(4) 0.102(13) Uiso 1 1 d . . . H5A H 0.2340(12) 0.039(4) 0.646(3) 0.059(10) Uiso 1 1 d . . . H6A H 0.2700(14) 0.170(4) 0.447(3) 0.078(11) Uiso 1 1 d . . . H5B H 0.1757(12) 0.142(4) 0.618(3) 0.067(10) Uiso 1 1 d . . . H3A H 0.1759(12) -0.244(4) 0.614(3) 0.060(10) Uiso 1 1 d . . . H6B H 0.2135(12) 0.272(4) 0.423(3) 0.065(11) Uiso 1 1 d . . . C1 C 0.09439(19) -0.4889(5) 0.5076(3) 0.0575(10) Uani 1 1 d . . . C2 C 0.12424(19) -0.3471(5) 0.4329(3) 0.0590(10) Uani 1 1 d . . . C3 C 0.1488(2) -0.2002(5) 0.5340(4) 0.0603(10) Uani 1 1 d . . . C4 C 0.1820(2) -0.0612(5) 0.4647(4) 0.0626(11) Uani 1 1 d . . . C5 C 0.2074(2) 0.0855(5) 0.5665(4) 0.0639(10) Uani 1 1 d . . . C6 C 0.2406(2) 0.2237(5) 0.4963(4) 0.0691(11) Uani 1 1 d . . . C7 C 0.2686(2) 0.3664(5) 0.5975(4) 0.0727(12) Uani 1 1 d . . . C8 C 0.30120(16) 0.5052(5) 0.5266(4) 0.0787(12) Uani 1 1 d . . . H8A H 0.3314 0.4471 0.4829 0.094 Uiso 1 1 calc R . . H8B H 0.2741 0.5607 0.4486 0.094 Uiso 1 1 calc R . . C9 C 0.3295(2) 0.6476(5) 0.6280(5) 0.0788(12) Uani 1 1 d . . . C10 C 0.36202(19) 0.7861(5) 0.5590(4) 0.0986(13) Uani 1 1 d . . . H10A H 0.3350 0.8405 0.4801 0.118 Uiso 1 1 calc R . . H10B H 0.3924 0.7279 0.5161 0.118 Uiso 1 1 calc R . . C11 C 0.3900(3) 0.9301(7) 0.6580(6) 0.1018(16) Uani 1 1 d . . . C12 C 0.4221(4) 1.0659(10) 0.5832(10) 0.146(3) Uani 1 1 d . . . C13 C 0.4520(2) 1.2051(8) 0.6836(7) 0.199(3) Uani 1 1 d . . . H13A H 0.4246 1.2553 0.7390 0.298 Uiso 1 1 calc R . . H13B H 0.4666 1.2966 0.6274 0.298 Uiso 1 1 calc R . . H13C H 0.4841 1.1529 0.7488 0.298 Uiso 1 1 calc R . . C1U C 0.04618(14) -0.7743(4) 0.4526(3) 0.0513(9) Uani 1 1 d . . . N1 N 0.07143(12) -0.6289(4) 0.4083(3) 0.0578(9) Uani 1 1 d . . . N2 N 0.02650(16) -0.8941(4) 0.3479(3) 0.0693(10) Uani 1 1 d . . . O1 O 0.04130(10) -0.7972(3) 0.58145(19) 0.0641(7) Uani 1 1 d . . . H2 H 0.0274(11) -0.872(4) 0.260(3) 0.050(9) Uiso 1 1 d . . . H3B H 0.1170(13) -0.154(4) 0.576(3) 0.063(10) Uiso 1 1 d . . . H1 H 0.0738(13) -0.612(4) 0.326(3) 0.068(11) Uiso 1 1 d . . . H3 H 0.0057(15) -0.972(5) 0.376(4) 0.087(14) Uiso 1 1 d . . . H11B H 0.359(2) 0.992(7) 0.697(5) 0.15(2) Uiso 1 1 d . . . H12A H 0.455(2) 1.005(9) 0.559(7) 0.22(4) Uiso 1 1 d . . . H12B H 0.399(3) 1.107(9) 0.500(6) 0.19(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.088(3) 0.042(2) 0.0435(19) -0.0024(17) 0.014(2) -0.006(2) C2 0.082(3) 0.044(2) 0.051(2) -0.0003(17) 0.012(2) -0.011(2) C3 0.086(3) 0.044(2) 0.052(2) 0.0013(19) 0.014(2) -0.007(2) C4 0.086(3) 0.050(3) 0.053(2) -0.0015(19) 0.013(2) -0.011(2) C5 0.093(3) 0.046(2) 0.053(2) 0.0018(19) 0.012(2) -0.009(2) C6 0.100(3) 0.048(3) 0.061(2) -0.004(2) 0.018(2) -0.011(2) C7 0.099(3) 0.057(3) 0.065(2) -0.003(2) 0.021(2) -0.018(2) C8 0.106(3) 0.058(3) 0.073(2) -0.003(2) 0.017(2) -0.017(2) C9 0.099(3) 0.056(3) 0.080(3) -0.004(2) 0.012(3) -0.016(3) C10 0.123(3) 0.073(3) 0.101(3) -0.014(3) 0.026(3) -0.028(3) C11 0.104(4) 0.073(4) 0.127(4) -0.013(3) 0.013(4) -0.023(3) C12 0.153(7) 0.101(5) 0.193(8) -0.027(5) 0.049(7) -0.054(5) C13 0.177(6) 0.125(5) 0.287(8) -0.038(5) 0.018(5) -0.070(5) C1U 0.082(2) 0.036(2) 0.0362(17) 0.0034(15) 0.0126(16) 0.0012(18) N1 0.099(2) 0.0406(18) 0.0354(15) 0.0002(13) 0.0151(15) -0.0151(15) N2 0.127(3) 0.048(2) 0.0352(16) -0.0035(15) 0.0202(17) -0.0222(19) O1 0.1178(19) 0.0417(13) 0.0362(11) -0.0027(10) 0.0227(10) -0.0101(13)