Competition between hydrogen bonding and dispersion interactions in the crystal structures of the primary amines
Maloney, Andrew G. P.; Wood, Peter A.; Parsons, Simon; CrystEngComm 16 (2014) 3867–; doi:10.1039/c3ce42639d

data_7214422
_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         'C5 H13 N1'
_chemical_formula_sum            'C5 H13 N'
_chemical_formula_weight         87.16
_chemical_melting_point          223
_chemical_name_systematic        pentylamine
_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   difmap
_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                   33.546(4)
_cell_length_b                   6.4878(8)
_cell_length_c                   5.7295(7)
_cell_measurement_reflns_used    1184
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     1247.0(3)
_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  0.075
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7311
_diffrn_reflns_theta_full        26.397
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         1.214
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             400
_exptl_crystal_size_max          2.000
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9616
_refine_ls_hydrogen_treatment    'restrained refall'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1274
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.0004202
_refine_ls_shift/su_mean         0.0000555
_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: 
 6.39 9.50 4.21 0.885 0.147E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1959
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1959
_reflns_limit_h_max              41
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                547
_reflns_number_total             1275
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      41.58
_oxford_refine_ls_r_factor_ref   0.1555
_oxford_refine_ls_scale          0.1778(3)
_oxford_reflns_number_all        1274
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Pentylamine in Pbcn'
_cod_data_source_file            c3ce42639d11.cif
_cod_data_source_block           pentylamine
_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        'C5 H13 N1'
_cod_database_code               7214422
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    6 ) 
CONT H    (   21 ,X'S,U[ISO])  UNTIL H    (   51 ) 
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(12) 
CONT N ( 1) TO H(11) 
REST 0.038, 0.002 = H(12,U[ISO]) 
REST 0.038, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(12) 
CONT C(2) TO N ( 1) TO H(11) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(21) 
CONT C ( 2) TO H(22) 
REST 0.035, 0.002 = H(21,U[ISO]) 
REST 0.035, 0.002 = H(22,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(21) TO C ( 2) TO H(22) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(31) 
CONT C ( 3) TO H(32) 
REST 0.035, 0.002 = H(31,U[ISO]) 
REST 0.035, 0.002 = H(32,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(31) TO C ( 3) TO H(32) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.043, 0.002 = H(42,U[ISO]) 
REST 0.043, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(52) 
CONT C ( 5) TO H(51) 
REST 0.058, 0.002 = H(52,U[ISO]) 
REST 0.058, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(52) TO C ( 5) TO H(51) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 6) TO H(63) 
CONT C ( 6) TO H(61) 
CONT C ( 6) TO H(62) 
REST 0.106, 0.002 = H(63,U[ISO]) 
REST 0.106, 0.002 = H(61,U[ISO]) 
REST 0.106, 0.002 = H(62,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(5) TO C ( 6) TO H(63) 
CONT C(5) TO C ( 6) TO H(61) 
CONT C(5) TO C ( 6) TO H(62) 
ANGLE 0.0, 2.0 = MEAN H(63) TO C ( 6) TO H(61) 
CONT H(63) TO C ( 6) TO H(62) 
CONT H(61) TO C ( 6) TO H(62) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;