#------------------------------------------------------------------------------ #$Date: 2014-04-16 06:33:57 +0300 (Wed, 16 Apr 2014) $ #$Revision: 109533 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/44/7214420.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_7214420 loop_ _publ_author_name 'Maloney, Andrew G. P.' 'Wood, Peter A.' 'Parsons, Simon' _publ_section_title ; Competition between hydrogen bonding and dispersion interactions in the crystal structures of the primary amines ; _journal_issue 19 _journal_name_full CrystEngComm _journal_page_first 3867 _journal_paper_doi 10.1039/c3ce42639d _journal_volume 16 _journal_year 2014 _chemical_compound_source Aldrich _chemical_formula_moiety 'C3 H9 N1' _chemical_formula_sum 'C3 H9 N' _chemical_formula_weight 59.11 _chemical_melting_point 190 _chemical_name_systematic propylamine _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 11-02-01 _audit_creation_method CRYSTALS_ver_14.11 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 23.2870(13) _cell_length_b 6.2354(4) _cell_length_c 5.9794(4) _cell_measurement_reflns_used 2006 _cell_measurement_temperature 150 _cell_measurement_theta_max 26 _cell_measurement_theta_min 4 _cell_volume 868.23(9) _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 9836 _diffrn_reflns_theta_full 26.400 _diffrn_reflns_theta_max 26.400 _diffrn_reflns_theta_min 1.749 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.055 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 0.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 272 _exptl_crystal_size_max 2.000 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.29 _refine_diff_density_min -0.29 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9898 _refine_ls_hydrogen_treatment 'restrained refall' _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 883 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0777 _refine_ls_R_factor_gt 0.0598 _refine_ls_shift/su_max 0.0004408 _refine_ls_shift/su_mean 0.0000219 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.53 14.0 5.18 0.123 -0.495 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1494 _refine_ls_wR_factor_gt 0.1337 _refine_ls_wR_factor_ref 0.1494 _reflns_limit_h_max 28 _reflns_limit_h_min 0 _reflns_limit_k_max 7 _reflns_limit_k_min 0 _reflns_limit_l_max 7 _reflns_limit_l_min 0 _reflns_number_gt 690 _reflns_number_total 890 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.01 _oxford_diffrn_Wilson_scale 14.44 _oxford_refine_ls_r_factor_ref 0.0777 _oxford_refine_ls_scale 0.2689(9) _oxford_reflns_number_all 883 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'Propylamine in Pbcn' _[local]_cod_data_source_file c3ce42639d11.cif _[local]_cod_data_source_block propylamine _[local]_cod_cif_authors_sg_H-M 'P b c n ' _[local]_cod_chemical_formula_sum_orig 'C3 H9 N1' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_atom_sites_solution_primary' value 'Direct' changed to 'direct' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 7214420 _iucr_refine_instruction_details_constraints ; BLOCK CONT SCALE CONT N ( 1 ,X'S,U'S) UNTIL C ( 4 ) CONT H ( 22 ,X'S,U[ISO]) UNTIL H ( 42 ) END ; _iucr_refine_instruction_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 H2-N-R DIST 0.86, 0.02 = CONT N ( 1) TO H(11) CONT N ( 1) TO H(12) REST 0.041, 0.002 = H(11,U[ISO]) REST 0.041, 0.002 = H(12,U[ISO]) ANGLE 120.0, 2.0 = CONT C(2) TO N ( 1) TO H(11) CONT C(2) TO N ( 1) TO H(12) REM 2 H ON SP 3 DIST 0.97, 0.02 = CONT C ( 2) TO H(22) CONT C ( 2) TO H(21) REST 0.037, 0.002 = H(22,U[ISO]) REST 0.037, 0.002 = H(21,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(22) TO C ( 2) TO N(1) CONT H(22) TO C ( 2) TO C(3) CONT H(21) TO C ( 2) TO N(1) CONT H(21) TO C ( 2) TO C(3) ANGLE 109.54, 2.0 = CONT H(22) TO C ( 2) TO H(21) REM 2 H ON SP 3 DIST 0.97, 0.02 = CONT C ( 3) TO H(32) CONT C ( 3) TO H(31) REST 0.045, 0.002 = H(32,U[ISO]) REST 0.045, 0.002 = H(31,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(32) TO C ( 3) TO C(2) CONT H(32) TO C ( 3) TO C(4) CONT H(31) TO C ( 3) TO C(2) CONT H(31) TO C ( 3) TO C(4) ANGLE 109.54, 2.0 = CONT H(32) TO C ( 3) TO H(31) REM 3 H ON SP 3 DIST 0.96, 0.02 = CONT C ( 4) TO H(41) CONT C ( 4) TO H(43) CONT C ( 4) TO H(42) REST 0.090, 0.002 = H(41,U[ISO]) REST 0.090, 0.002 = H(43,U[ISO]) REST 0.090, 0.002 = H(42,U[ISO]) ANGLE 109.54, 2.0 = CONT C(3) TO C ( 4) TO H(41) CONT C(3) TO C ( 4) TO H(43) CONT C(3) TO C ( 4) TO H(42) ANGLE 0.0, 2.0 = MEAN H(41) TO C ( 4) TO H(43) CONT H(41) TO C ( 4) TO H(42) CONT H(43) TO C ( 4) TO H(42) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y,z+1/2 -x,y,-z+1/2 -x+1/2,-y+1/2,z+1/2 x+1/2,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 N1 N 0.72466(5) 0.7067(2) 0.5121(2) 0.0338 1.0000 Uani D C2 C 0.66843(5) 0.7878(2) 0.4443(2) 0.0308 1.0000 Uani D C3 C 0.61693(6) 0.6954(2) 0.5682(2) 0.0375 1.0000 Uani D C4 C 0.56034(7) 0.7791(4) 0.4763(4) 0.0602 1.0000 Uani D H22 H 0.6701(5) 0.945(2) 0.461(2) 0.0371(18) 1.0000 Uiso D H11 H 0.7278(5) 0.569(2) 0.495(3) 0.0401(18) 1.0000 Uiso D H21 H 0.6651(5) 0.758(2) 0.286(2) 0.0364(18) 1.0000 Uiso D H32 H 0.6207(6) 0.730(2) 0.724(2) 0.0456(18) 1.0000 Uiso D H31 H 0.6178(5) 0.540(2) 0.557(2) 0.0451(18) 1.0000 Uiso D H12 H 0.7299(6) 0.728(2) 0.655(2) 0.0413(18) 1.0000 Uiso D H41 H 0.5568(8) 0.739(3) 0.320(3) 0.089(2) 1.0000 Uiso D H43 H 0.5285(7) 0.720(3) 0.561(3) 0.0898(19) 1.0000 Uiso D H42 H 0.5599(7) 0.934(3) 0.490(3) 0.0889(19) 1.0000 Uiso 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 N1 0.0300(6) 0.0352(7) 0.0361(7) 0.0020(5) -0.0019(4) 0.0018(4) C2 0.0291(8) 0.0332(8) 0.0301(7) 0.0012(5) -0.0007(4) 0.0014(5) C3 0.0326(8) 0.0429(9) 0.0369(8) 0.0005(6) 0.0039(5) -0.0013(6) C4 0.0285(9) 0.0845(14) 0.0677(12) 0.0013(10) 0.0027(7) 0.0054(8) 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' 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 N1 H11 112.6(8) no C2 N1 H12 110.2(9) no H11 N1 H12 104.6(14) no N1 C2 C3 116.09(13) yes N1 C2 H22 106.2(7) no C3 C2 H22 111.0(7) no N1 C2 H21 106.2(7) no C3 C2 H21 109.9(7) no H22 C2 H21 107.0(10) no C2 C3 C4 112.14(15) yes C2 C3 H32 108.4(8) no C4 C3 H32 110.7(8) no C2 C3 H31 109.2(8) no C4 C3 H31 109.7(7) no H32 C3 H31 106.7(11) no C3 C4 H41 109.4(11) no C3 C4 H43 110.0(11) no H41 C4 H43 110.0(13) no C3 C4 H42 108.7(10) no H41 C4 H42 109.6(13) no H43 C4 H42 109.1(13) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.4610(16) yes N1 H11 0.866(13) no N1 H12 0.871(14) no C2 C3 1.5229(18) yes C2 H22 0.984(13) no C2 H21 0.970(13) no C3 C4 1.520(2) yes C3 H32 0.961(14) no C3 H31 0.969(13) no C4 H41 0.972(17) no C4 H43 0.972(16) no C4 H42 0.968(16) 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 N1 H11 N1 3_645 156.9(11) 0.866(13) 2.520(13) 3.334(2) yes N1 H12 N1 7_665 162.0(12) 0.871(14) 2.419(14) 3.259(2) yes