#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/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       ω
_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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai 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>2.0σ(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'
_cod_data_source_file            c3ce42639d11.cif
_cod_data_source_block           propylamine
_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_original_sg_symbol_H-M      'P b c n '
_cod_original_formula_sum        'C3 H9 N1'
_cod_database_code               7214420
#BEGIN Tags that were not found in dictionaries:
_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                                                                             
;
#END Tags that were not found in dictionaries
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
