#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/23/2102304.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_2102304 loop_ _publ_author_name 'Parkin, Andrew' 'Oswald, Iain D. H.' 'Parsons, Simon' _publ_section_title ; Structures of piperazine, piperidine and morpholine ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 219 _journal_page_last 227 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety ' C4 H9 N1 O1 ' _chemical_formula_sum 'C4 H9 N O' _chemical_formula_weight 87.12 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom/difmap _atom_sites_solution_primary direct _audit_creation_method CRYSTALS_ver_12-03-99 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2311(5) _cell_length_b 8.2292(7) _cell_length_c 11.1370(10) _cell_measurement_reflns_used 3398 _cell_measurement_temperature 150 _cell_measurement_theta_max 29 _cell_measurement_theta_min 2 _cell_volume 479.42(7) _computing_cell_refinement ; SAINT (Bruker-AXS, 2002) ; _computing_data_collection ; SMART (Bruker-AXS, 2002) ; _computing_data_reduction ; SAINT (Bruker-AXS, 2002) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1993) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_structure_solution ; SHELXTL (Sheldrick, 1997a) ; _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.945 _diffrn_measurement_device_type ; Bruker SMART ; _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4211 _diffrn_reflns_theta_full 27.322 _diffrn_reflns_theta_max 28.685 _diffrn_reflns_theta_min 3.078 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS (Siemens, 1996) ; _exptl_crystal_colour ' colourless ' _exptl_crystal_density_diffrn 1.207 _exptl_crystal_description ' cylinder ' _exptl_crystal_F_000 192.000 _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.19 _refine_diff_density_min -0.24 _refine_ls_extinction_coef 17.E1(3) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _refine_ls_goodness_of_fit_ref 1.1148 _refine_ls_hydrogen_treatment noref/refall _refine_ls_matrix_type full _refine_ls_number_parameters 60 _refine_ls_number_reflns 699 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0441 _refine_ls_shift/su_max 0.000859 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method = SHELXL 97 (Sheldrick, 1997) w = 1/[sigma^2^(F~o~^2^) + (0.03P)^2^ + 0.15P], where P=1/2max(F^2^~o~,0)+2/3F~c~^2^ ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1057 _refine_ls_wR_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.1057 _reflns_number_gt 655 _reflns_number_total 703 _reflns_threshold_expression I>2.00u(I) _[local]_cod_data_source_file av5005.cif _[local]_cod_data_source_block c4h9no _[local]_cod_cif_authors_sg_H-M 'P 21 21 21 ' _[local]_cod_chemical_formula_sum_orig ' C4 H9 N1 O1 ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2102304 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_site_label _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_type_symbol O1 0.1318(3) 0.13035(18) 0.12024(13) 0.0282 Uani 1.0000 O C2 0.1757(5) 0.0668(3) 0.00229(19) 0.0259 Uani 1.0000 C C3 -0.0624(5) -0.0136(2) -0.04753(18) 0.0228 Uani 1.0000 C N4 -0.1399(4) -0.1443(2) 0.03416(15) 0.0210 Uani 1.0000 N C5 -0.1921(4) -0.0755(3) 0.15333(17) 0.0229 Uani 1.0000 C C6 0.0489(5) 0.0045(3) 0.19886(18) 0.0269 Uani 1.0000 C H4 -0.282(6) -0.192(3) 0.008(2) 0.036(8) Uiso 1.0000 H H21 0.2261 0.1560 -0.0510 0.0313 Uiso 1.0000 H H22 0.3137 -0.0136 0.0060 0.0313 Uiso 1.0000 H H31 -0.0259 -0.0588 -0.1271 0.0276 Uiso 1.0000 H H32 -0.2001 0.0667 -0.0540 0.0276 Uiso 1.0000 H H51 -0.2439 -0.1622 0.2085 0.0276 Uiso 1.0000 H H52 -0.3292 0.0053 0.1475 0.0276 Uiso 1.0000 H H61 0.0156 0.0510 0.2783 0.0325 Uiso 1.0000 H H62 0.1840 -0.0776 0.2051 0.0325 Uiso 1.0000 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0343(9) 0.0260(8) 0.0242(8) -0.0087(8) 0.0024(7) -0.0055(6) C2 0.0299(12) 0.0240(10) 0.0240(10) -0.0060(10) 0.0045(9) -0.0018(9) C3 0.0278(11) 0.0220(9) 0.0185(9) 0.0016(9) -0.0012(8) -0.0020(8) N4 0.0207(9) 0.0192(8) 0.0232(9) -0.0028(8) -0.0009(7) -0.0005(7) C5 0.0227(11) 0.0237(9) 0.0222(9) -0.0010(10) 0.0020(8) 0.0028(8) C6 0.0276(11) 0.0314(11) 0.0220(10) -0.0011(11) -0.0013(9) 0.0003(9) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 0.0033 0.0016 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 International_Tables_Vol_IV_Table_2.2B 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 C2 O1 C6 110.32(16) yes O1 C2 C3 111.31(18) yes O1 C2 H21 108.998 no C3 C2 H21 109.026 no O1 C2 H22 108.999 no C3 C2 H22 109.027 no H21 C2 H22 109.458 no C2 C3 N4 108.69(17) yes C2 C3 H31 109.682 no N4 C3 H31 109.658 no C2 C3 H32 109.673 no N4 C3 H32 109.654 no H31 C3 H32 109.467 no C3 N4 C5 109.25(15) yes C3 N4 H4 110.7(18) no C5 N4 H4 108.1(17) no N4 C5 C6 108.43(18) yes N4 C5 H51 109.738 no C6 C5 H51 109.721 no N4 C5 H52 109.730 no C6 C5 H52 109.719 no H51 C5 H52 109.487 no O1 C6 C5 111.41(17) yes O1 C6 H61 108.983 no C5 C6 H61 108.986 no O1 C6 H62 108.983 no C5 C6 H62 108.991 no H61 C6 H62 109.469 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.432(2) yes O1 C6 1.424(3) yes C2 C3 1.516(3) yes C2 H21 0.980 no C2 H22 0.980 no C3 N4 1.466(3) yes C3 H31 0.980 no C3 H32 0.980 no N4 C5 1.468(2) yes N4 H4 0.89(3) no C5 C6 1.510(3) yes C5 H51 0.980 no C5 H52 0.980 no C6 H61 0.980 no C6 H62 0.980 no _journal_paper_doi 10.1107/S0108768104003672