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_7214427
_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_absolute_configuration unk
_chemical_compound_source        Aldrich
_chemical_formula_moiety         'C10 H23 N1'
_chemical_formula_sum            'C10 H23 N'
_chemical_formula_weight         157.30
_chemical_melting_point          284
_chemical_name_systematic        decylamine
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             11-02-18
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0660(4)
_cell_length_b                   26.8352(15)
_cell_length_c                   5.5730(3)
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1056.74(10)
_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 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9645
_diffrn_reflns_theta_full        26.033
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_min         1.518
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             360
_exptl_crystal_size_max          2.000
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9762
_refine_ls_hydrogen_treatment    'restrained refall'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.0002583
_refine_ls_shift/su_mean         0.0000195
_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: 
 2.90 4.25 1.98 0.539 -0.465E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1229
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1229
_reflns_limit_h_max              9
_reflns_limit_h_min              0
_reflns_limit_k_max              34
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                1182
_reflns_number_total             1286
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0592
_oxford_refine_ls_scale          0.1792(3)
_oxford_reflns_number_all        1281
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Decylamine in Pca2(1)'
_cod_data_source_file            c3ce42639d11.cif
_cod_data_source_block           decylamine
_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 c a 21 '
_cod_original_formula_sum        'C10 H23 N1'
_cod_database_code               7214427
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    2 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   21 ) 
CONT C    (    3 ,X'S,U'S) 
CONT H    (   32 ,X'S,U[ISO])  UNTIL H    (   31 ) 
CONT C    (    4 ,X'S,U'S) 
CONT H    (   41 ,X'S,U[ISO]) 
CONT C    (    5 ,X'S,U'S) 
CONT H    (   51 ,X'S,U[ISO])  UNTIL H    (   52 ) 
CONT C    (    6 ,X'S,U'S) 
CONT H    (   61 ,X'S,U[ISO])  UNTIL H    (   62 ) 
CONT C    (    7 ,X'S,U'S) 
CONT H    (   71 ,X'S,U[ISO])  UNTIL H    (   72 ) 
CONT C    (    8 ,X'S,U'S) 
CONT H    (   81 ,X'S,U[ISO])  UNTIL H    (   82 ) 
CONT C    (    9 ,X'S,U'S) 
CONT H    (   91 ,X'S,U[ISO])  UNTIL H    (   92 ) 
CONT C    (   10 ,X'S,U'S) 
CONT H    (  101 ,X'S,U[ISO])  UNTIL H    (  102 ) 
CONT C    (   11 ,X'S,U'S) 
CONT H    (  112 ,X'S,U[ISO])  UNTIL H    (   42 ) 
END                                                                             
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_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 0.033, 0.002 = H(12,U[ISO]) 
REST 0.033, 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(22) 
CONT C ( 2) TO H(21) 
REST 0.028, 0.002 = H(22,U[ISO]) 
REST 0.028, 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 0.025, 0.002 = H(32,U[ISO]) 
REST 0.025, 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            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(41) 
CONT C ( 4) TO H(42) 
REST 0.025, 0.002 = H(41,U[ISO]) 
REST 0.025, 0.002 = H(42,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(41) TO C ( 4) TO H(42) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(51) 
CONT C ( 5) TO H(52) 
REST 0.025, 0.002 = H(51,U[ISO]) 
REST 0.025, 0.002 = H(52,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(51) TO C ( 5) TO H(52) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(61) 
CONT C ( 6) TO H(62) 
REST 0.027, 0.002 = H(61,U[ISO]) 
REST 0.027, 0.002 = H(62,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
CONT H(62) TO C ( 6) TO C(5) 
CONT H(62) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(61) TO C ( 6) TO H(62) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 7) TO H(71) 
CONT C ( 7) TO H(72) 
REST 0.026, 0.002 = H(71,U[ISO]) 
REST 0.026, 0.002 = H(72,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(8) 
CONT H(72) TO C ( 7) TO C(6) 
CONT H(72) TO C ( 7) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(71) TO C ( 7) TO H(72) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 8) TO H(81) 
CONT C ( 8) TO H(82) 
REST 0.029, 0.002 = H(81,U[ISO]) 
REST 0.029, 0.002 = H(82,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
CONT H(82) TO C ( 8) TO C(7) 
CONT H(82) TO C ( 8) TO C(9) 
ANGLE 109.54, 2.0 = 
CONT H(81) TO C ( 8) TO H(82) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 9) TO H(91) 
CONT C ( 9) TO H(92) 
REST 0.029, 0.002 = H(91,U[ISO]) 
REST 0.029, 0.002 = H(92,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
CONT H(92) TO C ( 9) TO C(8) 
CONT H(92) TO C ( 9) TO C(10) 
ANGLE 109.54, 2.0 = 
CONT H(91) TO C ( 9) TO H(92) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 10) TO H(101) 
CONT C ( 10) TO H(102) 
REST 0.035, 0.002 = H(101,U[ISO]) 
REST 0.035, 0.002 = H(102,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
CONT H(102) TO C ( 10) TO C(9) 
CONT H(102) TO C ( 10) TO C(11) 
ANGLE 109.54, 2.0 = 
CONT H(101) TO C ( 10) TO H(102) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 11) TO H(112) 
CONT C ( 11) TO H(113) 
CONT C ( 11) TO H(111) 
REST 0.054, 0.002 = H(112,U[ISO]) 
REST 0.054, 0.002 = H(113,U[ISO]) 
REST 0.054, 0.002 = H(111,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(10) TO C ( 11) TO H(112) 
CONT C(10) TO C ( 11) TO H(113) 
CONT C(10) TO C ( 11) TO H(111) 
ANGLE 0.0, 2.0 = MEAN H(112) TO C ( 11) TO H(113) 
CONT H(112) TO C ( 11) TO H(111) 
CONT H(113) TO C ( 11) TO H(111) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;