# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DBA100K_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pqp
_database_code_depnum_ccdc_archive 'CCDC 1826573'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT049_DBA100K_0m          
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9771 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            dibutylamine
_chemical_formula_sum            'C8 H19 N'
_chemical_formula_weight         129.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   4.8201(15)
_cell_length_b                   7.003(2)
_cell_length_c                   26.028(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     878.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3400
_cell_measurement_theta_min      6.261
_cell_measurement_theta_max      52.600

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.977
_exptl_crystal_F_000             296
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4576
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            11205
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.131
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             874
_reflns_number_gt                723
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1080P)²+0.3217P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         874
_refine_ls_number_parameters     47
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1683
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8302(3) 0.0610(3) 0.2500 0.0183(5) Uani 1 2 d S T P . .
H1 H 0.819(5) -0.064(4) 0.2500 0.035(7) Uiso 1 2 d S . P . .
C1 C 0.6949(2) 0.1337(2) 0.29629(4) 0.0171(4) Uani 1 1 d . . . . .
H1A H 0.4938 0.1058 0.2945 0.020 Uiso 1 1 calc R U . . .
H1B H 0.7179 0.2740 0.2979 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8145(2) 0.0449(2) 0.34466(4) 0.0169(4) Uani 1 1 d . . . . .
H2A H 1.0172 0.0678 0.3456 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7841 -0.0949 0.3437 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6838(2) 0.12614(19) 0.39325(4) 0.0193(4) Uani 1 1 d . . . . .
H3A H 0.7169 0.2656 0.3943 0.023 Uiso 1 1 calc R U . . .
H3B H 0.4807 0.1054 0.3919 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7973(3) 0.0366(2) 0.44220(5) 0.0247(5) Uani 1 1 d . . . . .
H4A H 0.7053 0.0937 0.4721 0.037 Uiso 1 1 calc R U . . .
H4B H 0.9975 0.0597 0.4443 0.037 Uiso 1 1 calc R U . . .
H4C H 0.7621 -0.1012 0.4417 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4614(14) . ?
N1 C1 1.4615(14) 6_556 ?
C1 C2 1.5178(15) . ?
C2 C3 1.5234(15) . ?
C3 C4 1.5216(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 111.05(14) . 6_556 ?
N1 C1 C2 111.82(11) . . ?
C1 C2 C3 112.25(11) . . ?
C4 C3 C2 113.11(11) . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060



_chemical_name_systematic        Dibutylamine
_chemical_formula_moiety         'C8 H19 N'
_chemical_melting_point          211
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dihexylamine_100K_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9prq
_database_code_depnum_ccdc_archive 'CCDC 1826574'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_dihexylamine_100K_0m 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.947 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_dihexylamine_100K_0m 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9915 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            dihexylamine
_chemical_formula_sum            'C12 H27 N'
_chemical_formula_weight         185.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   4.856(4)
_cell_length_b                   7.056(6)
_cell_length_c                   36.24(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1241.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    405
_cell_measurement_theta_min      4.496
_cell_measurement_theta_max      52.595

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.991
_exptl_crystal_F_000             424
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            3226
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             1216
_reflns_number_gt                595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1216
_refine_ls_number_parameters     65
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8304(4) 0.0609(3) 0.2500 0.0179(5) Uani 1 2 d S T P . .
H1 H 0.827(5) -0.056(3) 0.2500 0.024(7) Uiso 1 2 d S . P . .
C1 C 0.6961(3) 0.1323(2) 0.28340(3) 0.0164(4) Uani 1 1 d . . . . .
H1A H 0.4969 0.1031 0.2823 0.020 Uiso 1 1 calc R U . . .
H1B H 0.7168 0.2718 0.2845 0.020 Uiso 1 1 calc R U . . .
C2 C 0.8179(4) 0.0452(2) 0.31810(3) 0.0155(4) Uani 1 1 d . . . . .
H2A H 1.0189 0.0686 0.3185 0.019 Uiso 1 1 calc R U . . .
H2B H 0.7887 -0.0936 0.3175 0.019 Uiso 1 1 calc R U . . .
C3 C 0.6903(3) 0.1255(2) 0.35324(3) 0.0160(4) Uani 1 1 d . . . . .
H3A H 0.7202 0.2643 0.3537 0.019 Uiso 1 1 calc R U . . .
H3B H 0.4891 0.1030 0.3527 0.019 Uiso 1 1 calc R U . . .
C4 C 0.8077(3) 0.0395(2) 0.38845(3) 0.0157(4) Uani 1 1 d . . . . .
H4A H 1.0091 0.0609 0.3890 0.019 Uiso 1 1 calc R U . . .
H4B H 0.7758 -0.0990 0.3881 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6808(3) 0.1225(2) 0.42339(4) 0.0190(4) Uani 1 1 d . . . . .
H5A H 0.4791 0.1023 0.4227 0.023 Uiso 1 1 calc R U . . .
H5B H 0.7144 0.2608 0.4238 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7961(3) 0.0350(2) 0.45872(4) 0.0263(5) Uani 1 1 d . . . . .
H6A H 0.7086 0.0943 0.4802 0.039 Uiso 1 1 calc R U . . .
H6B H 0.9955 0.0561 0.4598 0.039 Uiso 1 1 calc R U . . .
H6C H 0.7584 -0.1014 0.4589 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.464(2) 6_556 ?
N1 C1 1.465(2) . ?
C1 C2 1.519(2) . ?
C2 C3 1.526(2) . ?
C3 C4 1.524(2) . ?
C4 C5 1.525(2) . ?
C5 C6 1.528(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 111.51(19) 6_556 . ?
N1 C1 C2 111.81(15) . . ?
C1 C2 C3 112.48(15) . . ?
C4 C3 C2 113.52(14) . . ?
C3 C4 C5 113.04(14) . . ?
C4 C5 C6 113.13(14) . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.044



_chemical_name_systematic        dihexylamine
_chemical_formula_moiety         'C12 H27 N'
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_twin5_160K
_audit_block_doi                 10.5517/ccdc.csd.cc1z9psr
_database_code_depnum_ccdc_archive 'CCDC 1826575'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_twin5_160K          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.850 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_twin5_160K          
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.8804 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            diethylamine
_chemical_formula_sum            'C4 H11 N'
_chemical_formula_weight         73.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.0789(19)
_cell_length_b                   15.538(4)
_cell_length_c                   13.319(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.065(4)
_cell_angle_gamma                90
_cell_volume                     1655.5(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    4724
_cell_measurement_theta_min      5.242
_cell_measurement_theta_max      51.871

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.880
_exptl_crystal_F_000             504
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6413
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            1408
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measured_fraction_theta_full 0.850
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_Laue_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_point_group_measured_fraction_full 0.850
_reflns_number_total             1408
_reflns_number_gt                1152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.4913P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     85
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0000 0.65166(9) 0.2500 0.0367(4) Uani 1 2 d DS T P . .
H1A H 0.928(3) 0.6185(13) 0.2668(17) 0.018(6) Uiso 0.5 1 d D . P . .
C11 C 1.0687(2) 0.70334(8) 0.33716(10) 0.0439(4) Uani 1 1 d . . . . .
H11A H 0.9818 0.7433 0.3549 0.053 Uiso 1 1 calc R U . . .
H11B H 1.1632 0.7381 0.3196 0.053 Uiso 1 1 calc R U . . .
C12 C 1.1287(2) 0.64700(10) 0.42738(11) 0.0527(5) Uani 1 1 d . . . . .
H12A H 1.0350 0.6128 0.4451 0.079 Uiso 1 1 calc R U . . .
H12B H 1.1733 0.6832 0.4851 0.079 Uiso 1 1 calc R U . . .
H12C H 1.2166 0.6084 0.4104 0.079 Uiso 1 1 calc R U . . .
N2 N 0.6833(2) 0.54751(9) 0.31594(10) 0.0495(4) Uani 1 1 d D . . . .
H2A H 0.598(3) 0.5495(15) 0.2724(17) 0.022(7) Uiso 0.5 1 d D . P . .
H2B H 0.747(3) 0.5811(14) 0.2927(18) 0.022(6) Uiso 0.5 1 d D . P . .
C21 C 0.7414(2) 0.45790(11) 0.32013(14) 0.0642(5) Uani 1 1 d . . . . .
H21A H 0.6588 0.4213 0.3482 0.077 Uiso 1 1 calc R U . . .
H21B H 0.8486 0.4539 0.3661 0.077 Uiso 1 1 calc R U . . .
C23 C 0.6505(3) 0.58068(14) 0.41289(12) 0.0711(6) Uani 1 1 d . . . . .
H23A H 0.7526 0.5749 0.4631 0.085 Uiso 1 1 calc R U . . .
H23B H 0.5609 0.5462 0.4371 0.085 Uiso 1 1 calc R U . . .
C22 C 0.7655(3) 0.42506(11) 0.21713(16) 0.0704(6) Uani 1 1 d . . . . .
H22A H 0.6583 0.4261 0.1724 0.106 Uiso 1 1 calc R U . . .
H22B H 0.8078 0.3659 0.2231 0.106 Uiso 1 1 calc R U . . .
H22C H 0.8460 0.4617 0.1887 0.106 Uiso 1 1 calc R U . . .
C24 C 0.5988(3) 0.67308(15) 0.40521(16) 0.0896(8) Uani 1 1 d . . . . .
H24A H 0.6892 0.7076 0.3838 0.134 Uiso 1 1 calc R U . . .
H24B H 0.5752 0.6933 0.4715 0.134 Uiso 1 1 calc R U . . .
H24C H 0.4981 0.6790 0.3553 0.134 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.4559(16) . ?
N1 C11 1.4559(15) 2_755 ?
C11 C12 1.511(2) . ?
N2 C23 1.449(2) . ?
N2 C21 1.468(2) . ?
C21 C22 1.502(3) . ?
C23 C24 1.495(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C11 113.04(14) . 2_755 ?
N1 C11 C12 111.01(11) . . ?
C23 N2 C21 113.65(14) . . ?
N2 C21 C22 111.67(13) . . ?
N2 C23 C24 111.41(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.829(17) 2.434(18) 3.2506(17) 168(2) .
N2 H2A N2 0.836(18) 2.41(2) 3.225(3) 165(2) 2_655
N2 H2B N1 0.823(18) 2.455(19) 3.2506(17) 163(2) .

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.026



_chemical_name_systematic        diethylamine
_chemical_formula_moiety         'C4 H11 N'
_chemical_melting_point          223
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NEIPA100K_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pwv
_database_code_depnum_ccdc_archive 'CCDC 1826578'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_NEIPA100K_0m        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.905 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_NEIPA100K_0m        
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9320 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ethylisopropylamine
_chemical_formula_sum            'C5 H13 N'
_chemical_formula_weight         87.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.933(18)
_cell_length_b                   9.062(19)
_cell_length_c                   15.56(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.55(3)
_cell_angle_gamma                90
_cell_volume                     1242(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1747
_cell_measurement_theta_min      4.936
_cell_measurement_theta_max      51.879

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.932
_exptl_crystal_F_000             400
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5852
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            7936
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         25.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             2086
_reflns_number_gt                1223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²+3.4298P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2086
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2534
_refine_ls_wR_factor_gt          0.2225
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1785(3) 0.2288(5) 0.1314(2) 0.0278(9) Uani 1 1 d . . . . .
H1 H 0.159(4) 0.187(5) 0.180(2) 0.010(9) Uiso 1 1 d . . . . .
C11 C 0.0385(4) 0.2902(6) 0.0824(3) 0.0314(12) Uani 1 1 d . . . . .
H11A H -0.0328 0.2090 0.0622 0.038 Uiso 1 1 calc R U . . .
H11B H 0.0616 0.3430 0.0305 0.038 Uiso 1 1 calc R U . . .
C12 C -0.0360(5) 0.3969(6) 0.1392(3) 0.0361(12) Uani 1 1 d . . . . .
H12A H -0.1328 0.4316 0.1065 0.054 Uiso 1 1 calc R U . . .
H12B H 0.0313 0.4814 0.1553 0.054 Uiso 1 1 calc R U . . .
H12C H -0.0541 0.3459 0.1921 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2559(5) 0.1261(6) 0.0808(3) 0.0316(12) Uani 1 1 d . . . . .
H13 H 0.1785 0.0608 0.0459 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3648(5) 0.0318(6) 0.1424(3) 0.0358(12) Uani 1 1 d . . . . .
H14A H 0.3091 -0.0204 0.1823 0.054 Uiso 1 1 calc R U . . .
H14B H 0.4427 0.0947 0.1759 0.054 Uiso 1 1 calc R U . . .
H14C H 0.4133 -0.0401 0.1088 0.054 Uiso 1 1 calc R U . . .
C15 C 0.3400(5) 0.2100(6) 0.0193(3) 0.0398(13) Uani 1 1 d . . . . .
H15A H 0.2682 0.2720 -0.0194 0.060 Uiso 1 1 calc R U . . .
H15B H 0.3879 0.1398 -0.0157 0.060 Uiso 1 1 calc R U . . .
H15C H 0.4181 0.2723 0.0530 0.060 Uiso 1 1 calc R U . . .
N2 N 0.0645(4) 0.0106(5) 0.2927(2) 0.0281(9) Uani 1 1 d . . . . .
H2 H 0.147(5) -0.054(6) 0.308(3) 0.039(13) Uiso 1 1 d . . . . .
C21 C 0.0348(4) 0.0911(6) 0.3694(3) 0.0306(11) Uani 1 1 d . . . . .
H21A H -0.0229 0.0273 0.4039 0.037 Uiso 1 1 calc R U . . .
H21B H -0.0278 0.1791 0.3507 0.037 Uiso 1 1 calc R U . . .
C22 C 0.1822(5) 0.1387(6) 0.4255(3) 0.0348(12) Uani 1 1 d . . . . .
H22A H 0.1597 0.1968 0.4750 0.052 Uiso 1 1 calc R U . . .
H22B H 0.2409 0.1989 0.3907 0.052 Uiso 1 1 calc R U . . .
H22C H 0.2411 0.0512 0.4471 0.052 Uiso 1 1 calc R U . . .
C23 C -0.0653(4) -0.0767(5) 0.2498(3) 0.0301(11) Uani 1 1 d . . . . .
H23 H -0.0988 -0.1440 0.2939 0.036 Uiso 1 1 calc R U . . .
C24 C -0.0138(5) -0.1694(6) 0.1795(3) 0.0355(12) Uani 1 1 d . . . . .
H24A H 0.0769 -0.2254 0.2044 0.053 Uiso 1 1 calc R U . . .
H24B H 0.0102 -0.1050 0.1330 0.053 Uiso 1 1 calc R U . . .
H24C H -0.0949 -0.2378 0.1554 0.053 Uiso 1 1 calc R U . . .
C25 C -0.1972(4) 0.0219(6) 0.2126(3) 0.0378(13) Uani 1 1 d . . . . .
H25A H -0.2275 0.0813 0.2595 0.057 Uiso 1 1 calc R U . . .
H25B H -0.2830 -0.0391 0.1858 0.057 Uiso 1 1 calc R U . . .
H25C H -0.1665 0.0873 0.1685 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.462(5) . ?
N1 C13 1.465(6) . ?
C11 C12 1.534(7) . ?
C13 C14 1.512(6) . ?
C13 C15 1.515(7) . ?
N2 C21 1.459(6) . ?
N2 C23 1.470(6) . ?
C21 C22 1.517(6) . ?
C23 C24 1.510(7) . ?
C23 C25 1.515(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C13 113.6(3) . . ?
N1 C11 C12 110.8(4) . . ?
N1 C13 C14 109.3(4) . . ?
N1 C13 C15 110.4(5) . . ?
C14 C13 C15 110.4(4) . . ?
C21 N2 C23 113.8(3) . . ?
N2 C21 C22 110.8(3) . . ?
N2 C23 C24 108.4(4) . . ?
N2 C23 C25 111.2(4) . . ?
C24 C23 C25 111.3(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.89(4) 2.61(4) 3.477(7) 164(3) .
N2 H2 N1 0.94(5) 2.59(5) 3.505(7) 165(4) 2_545

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058



_chemical_name_systematic        ethylisopropylamine
_chemical_formula_moiety         'C5 H13 N'
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MePrNH_hr_twin
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pzy
_database_code_depnum_ccdc_archive 'CCDC 1826581'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_MePrNH_hr_twin      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.865 Why?
RESPONSE: t
;
_vrf_PLAT049_MePrNH_hr_twin      
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9484 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            methylpropylamine
_chemical_formula_sum            'C4 H11 N'
_chemical_formula_weight         73.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.168(15)
_cell_length_b                   8.902(8)
_cell_length_c                   15.176(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.67(2)
_cell_angle_gamma                90
_cell_volume                     2049(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    883
_cell_measurement_theta_min      5.369
_cell_measurement_theta_max      54.839

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.948
_exptl_crystal_F_000             672
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            2659
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         25.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.865
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             2659
_reflns_number_gt                1817
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1832P)²+4.5703P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2920
_refine_ls_wR_factor_gt          0.2610
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5746(2) 0.0773(4) 0.6184(2) 0.0239(10) Uani 1 1 d . . . . .
H1 H 0.590(3) 0.071(6) 0.671(3) 0.035(14) Uiso 1 1 d . . . . .
C11 C 0.6128(3) 0.2020(6) 0.5701(3) 0.0277(12) Uani 1 1 d . . . . .
H11A H 0.6770 0.1901 0.5684 0.042 Uiso 1 1 calc R U . . .
H11B H 0.5983 0.2966 0.5995 0.042 Uiso 1 1 calc R U . . .
H11C H 0.5889 0.2031 0.5098 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5950(3) -0.0677(5) 0.5785(3) 0.0224(12) Uani 1 1 d . . . . .
H12A H 0.6596 -0.0773 0.5723 0.027 Uiso 1 1 calc R U . . .
H12B H 0.5680 -0.0725 0.5189 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5611(3) -0.1969(6) 0.6333(3) 0.0260(12) Uani 1 1 d . . . . .
H13A H 0.5902 -0.1943 0.6920 0.031 Uiso 1 1 calc R U . . .
H13B H 0.4970 -0.1839 0.6420 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5772(3) -0.3484(6) 0.5915(3) 0.0311(13) Uani 1 1 d . . . . .
H14A H 0.5460 -0.3537 0.5346 0.047 Uiso 1 1 calc R U . . .
H14B H 0.5555 -0.4278 0.6304 0.047 Uiso 1 1 calc R U . . .
H14C H 0.6406 -0.3620 0.5823 0.047 Uiso 1 1 calc R U . . .
N2 N 0.3642(2) 0.0943(4) 0.6777(2) 0.0252(11) Uani 1 1 d . . . . .
H2 H 0.416(3) 0.087(6) 0.662(3) 0.033(14) Uiso 1 1 d . . . . .
C21 C 0.3088(3) -0.0302(6) 0.6487(3) 0.0255(11) Uani 1 1 d . . . . .
H21A H 0.2513 -0.0234 0.6771 0.038 Uiso 1 1 calc R U . . .
H21B H 0.3372 -0.1254 0.6648 0.038 Uiso 1 1 calc R U . . .
H21C H 0.3008 -0.0256 0.5846 0.038 Uiso 1 1 calc R U . . .
C22 C 0.3261(3) 0.2394(5) 0.6526(3) 0.0209(11) Uani 1 1 d . . . . .
H22A H 0.2687 0.2522 0.6821 0.025 Uiso 1 1 calc R U . . .
H22B H 0.3153 0.2410 0.5882 0.025 Uiso 1 1 calc R U . . .
C23 C 0.3861(3) 0.3679(6) 0.6775(3) 0.0282(12) Uani 1 1 d . . . . .
H23A H 0.4441 0.3528 0.6498 0.034 Uiso 1 1 calc R U . . .
H23B H 0.3953 0.3680 0.7422 0.034 Uiso 1 1 calc R U . . .
C24 C 0.3491(3) 0.5191(6) 0.6492(3) 0.0315(13) Uani 1 1 d . . . . .
H24A H 0.3430 0.5218 0.5849 0.047 Uiso 1 1 calc R U . . .
H24B H 0.3892 0.5991 0.6687 0.047 Uiso 1 1 calc R U . . .
H24C H 0.2912 0.5341 0.6759 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.455(6) . ?
N1 C12 1.461(6) . ?
C12 C13 1.512(6) . ?
C13 C14 1.512(7) . ?
N2 C21 1.455(6) . ?
N2 C22 1.463(6) . ?
C22 C23 1.507(7) . ?
C23 C24 1.518(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 112.2(4) . . ?
N1 C12 C13 111.7(3) . . ?
C14 C13 C12 113.0(4) . . ?
C21 N2 C22 111.7(4) . . ?
N2 C22 C23 111.7(4) . . ?
C22 C23 C24 112.5(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.84(5) 2.39(5) 3.224(6) 171(5) 2_656
N2 H2 N1 0.82(5) 2.51(5) 3.329(6) 177(5) .

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.077



_chemical_name_systematic        methylpropylamine
_chemical_formula_moiety         'C4 H11 N'
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_EBA100KTHIRD_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9q00
_database_code_depnum_ccdc_archive 'CCDC 1826582'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_EBA100KTHIRD_0m     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.896 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_EBA100KTHIRD_0m     
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9187 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ethylbutylamine
_chemical_formula_sum            'C6 H15 N'
_chemical_formula_weight         101.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.348(4)
_cell_length_b                   8.940(3)
_cell_length_c                   17.768(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.637(4)
_cell_angle_gamma                90
_cell_volume                     2194.8(11)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6527
_cell_measurement_theta_min      4.760
_cell_measurement_theta_max      52.353

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.919
_exptl_crystal_F_000             696
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            18208
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.381
_diffrn_reflns_theta_max         26.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.896
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.895
_reflns_number_total             3192
_reflns_number_gt                3012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.875
_reflns_Friedel_fraction_full    0.895

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.2524P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     209
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.92863(17) 0.4298(2) 0.07831(12) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.897(2) 0.355(3) 0.0684(17) 0.023(7) Uiso 1 1 d . . . . .
C11 C 0.8602(2) 0.5506(3) 0.07892(17) 0.0293(7) Uani 1 1 d . . . . .
H11A H 0.8960 0.6461 0.0912 0.035 Uiso 1 1 calc R U . . .
H11B H 0.8276 0.5312 0.1205 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7848(2) 0.5649(3) 0.00155(18) 0.0359(7) Uani 1 1 d . . . . .
H12A H 0.7399 0.6457 0.0046 0.054 Uiso 1 1 calc R U . . .
H12B H 0.7491 0.4707 -0.0107 0.054 Uiso 1 1 calc R U . . .
H12C H 0.8166 0.5877 -0.0395 0.054 Uiso 1 1 calc R U . . .
C13 C 0.99955(19) 0.4129(2) 0.15345(14) 0.0209(6) Uani 1 1 d . . . . .
H13A H 0.9656 0.4013 0.1948 0.025 Uiso 1 1 calc R U . . .
H13B H 1.0398 0.5044 0.1650 0.025 Uiso 1 1 calc R U . . .
C14 C 1.06469(19) 0.2780(2) 0.15461(14) 0.0215(6) Uani 1 1 d . . . . .
H14A H 1.0241 0.1895 0.1347 0.026 Uiso 1 1 calc R U . . .
H14B H 1.1062 0.2970 0.1192 0.026 Uiso 1 1 calc R U . . .
C15 C 1.12849(19) 0.2445(2) 0.23614(14) 0.0214(6) Uani 1 1 d . . . . .
H15A H 1.0870 0.2123 0.2696 0.026 Uiso 1 1 calc R U . . .
H15B H 1.1621 0.3374 0.2588 0.026 Uiso 1 1 calc R U . . .
C16 C 1.2038(2) 0.1235(3) 0.23728(16) 0.0310(7) Uani 1 1 d . . . . .
H16A H 1.2395 0.1020 0.2915 0.046 Uiso 1 1 calc R U . . .
H16B H 1.2489 0.1584 0.2083 0.046 Uiso 1 1 calc R U . . .
H16C H 1.1713 0.0324 0.2128 0.046 Uiso 1 1 calc R U . . .
N2 N 0.80797(19) 0.0996(2) 0.05062(11) 0.0201(5) Uani 1 1 d . . . . .
H2 H 0.744(3) 0.096(3) 0.0324(18) 0.027(9) Uiso 1 1 d . . . . .
C21 C 0.8458(2) 0.0555(3) -0.01458(14) 0.0244(6) Uani 1 1 d . . . . .
H21A H 0.8249 -0.0479 -0.0308 0.029 Uiso 1 1 calc R U . . .
H21B H 0.9174 0.0570 0.0023 0.029 Uiso 1 1 calc R U . . .
C22 C 0.8102(2) 0.1604(3) -0.08332(14) 0.0280(6) Uani 1 1 d . . . . .
H22A H 0.8330 0.1251 -0.1275 0.042 Uiso 1 1 calc R U . . .
H22B H 0.8352 0.2612 -0.0685 0.042 Uiso 1 1 calc R U . . .
H22C H 0.7393 0.1626 -0.0984 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8340(2) -0.0085(2) 0.11495(15) 0.0248(6) Uani 1 1 d . . . . .
H23A H 0.9053 -0.0119 0.1356 0.030 Uiso 1 1 calc R U . . .
H23B H 0.8117 -0.1094 0.0949 0.030 Uiso 1 1 calc R U . . .
C24 C 0.7895(2) 0.0317(2) 0.18045(15) 0.0230(6) Uani 1 1 d . . . . .
H24A H 0.8029 -0.0502 0.2194 0.028 Uiso 1 1 calc R U . . .
H24B H 0.7184 0.0381 0.1587 0.028 Uiso 1 1 calc R U . . .
C25 C 0.8255(2) 0.1780(2) 0.22218(14) 0.0232(6) Uani 1 1 d . . . . .
H25A H 0.8960 0.1703 0.2467 0.028 Uiso 1 1 calc R U . . .
H25B H 0.8148 0.2599 0.1833 0.028 Uiso 1 1 calc R U . . .
C26 C 0.7752(2) 0.2168(3) 0.28450(16) 0.0346(7) Uani 1 1 d . . . . .
H26A H 0.8022 0.3099 0.3105 0.052 Uiso 1 1 calc R U . . .
H26B H 0.7851 0.1358 0.3230 0.052 Uiso 1 1 calc R U . . .
H26C H 0.7057 0.2297 0.2602 0.052 Uiso 1 1 calc R U . . .
N3 N 0.56985(17) 0.0929(2) -0.01696(13) 0.0230(5) Uani 1 1 d . . . . .
H3 H 0.540(2) 0.049(3) 0.0141(18) 0.027(8) Uiso 1 1 d . . . . .
C31 C 0.5504(2) 0.2543(3) -0.01901(17) 0.0288(7) Uani 1 1 d . . . . .
H31A H 0.4798 0.2715 -0.0382 0.035 Uiso 1 1 calc R U . . .
H31B H 0.5817 0.3029 -0.0559 0.035 Uiso 1 1 calc R U . . .
C32 C 0.5881(2) 0.3247(3) 0.06138(17) 0.0336(7) Uani 1 1 d . . . . .
H32A H 0.5759 0.4327 0.0577 0.050 Uiso 1 1 calc R U . . .
H32B H 0.6578 0.3066 0.0808 0.050 Uiso 1 1 calc R U . . .
H32C H 0.5548 0.2803 0.0974 0.050 Uiso 1 1 calc R U . . .
C33 C 0.5321(2) 0.0235(2) -0.09361(14) 0.0233(6) Uani 1 1 d . . . . .
H33A H 0.5603 0.0739 -0.1320 0.028 Uiso 1 1 calc R U . . .
H33B H 0.4610 0.0370 -0.1109 0.028 Uiso 1 1 calc R U . . .
C34 C 0.5557(2) -0.1427(2) -0.09158(15) 0.0233(6) Uani 1 1 d . . . . .
H34A H 0.6269 -0.1556 -0.0747 0.028 Uiso 1 1 calc R U . . .
H34B H 0.5284 -0.1923 -0.0524 0.028 Uiso 1 1 calc R U . . .
C35 C 0.5160(2) -0.2184(3) -0.17045(15) 0.0255(6) Uani 1 1 d . . . . .
H35A H 0.5438 -0.1694 -0.2094 0.031 Uiso 1 1 calc R U . . .
H35B H 0.4449 -0.2045 -0.1875 0.031 Uiso 1 1 calc R U . . .
C36 C 0.5387(2) -0.3854(3) -0.16839(17) 0.0333(7) Uani 1 1 d . . . . .
H36A H 0.5111 -0.4286 -0.2203 0.050 Uiso 1 1 calc R U . . .
H36B H 0.5105 -0.4349 -0.1304 0.050 Uiso 1 1 calc R U . . .
H36C H 0.6090 -0.3999 -0.1531 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.452(3) . ?
N1 C11 1.462(3) . ?
C11 C12 1.508(4) . ?
C13 C14 1.523(3) . ?
C14 C15 1.521(3) . ?
C15 C16 1.525(4) . ?
N2 C21 1.460(3) . ?
N2 C23 1.466(3) . ?
C21 C22 1.515(3) . ?
C23 C24 1.514(4) . ?
C24 C25 1.524(3) . ?
C25 C26 1.516(4) . ?
N3 C33 1.461(3) . ?
N3 C31 1.468(3) . ?
C31 C32 1.521(4) . ?
C33 C34 1.522(3) . ?
C34 C35 1.522(3) . ?
C35 C36 1.526(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C11 112.07(19) . . ?
N1 C11 C12 112.0(2) . . ?
N1 C13 C14 111.73(18) . . ?
C15 C14 C13 112.26(19) . . ?
C14 C15 C16 113.3(2) . . ?
C21 N2 C23 111.68(19) . . ?
N2 C21 C22 110.8(2) . . ?
N2 C23 C24 111.8(2) . . ?
C23 C24 C25 114.8(2) . . ?
C26 C25 C24 112.7(2) . . ?
C33 N3 C31 112.0(2) . . ?
N3 C31 C32 111.5(2) . . ?
N3 C33 C34 111.59(19) . . ?
C35 C34 C33 112.74(19) . . ?
C34 C35 C36 112.9(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.80(3) 2.59(3) 3.391(3) 173(3) .
N2 H2 N3 0.89(3) 2.41(4) 3.303(4) 178(2) .
N3 H3 N1 0.87(3) 2.45(3) 3.309(3) 168(3) 3_445

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027



_chemical_name_systematic        ethylbutylamine
_chemical_formula_moiety         'C6 H15 N'
_chemical_melting_point          195
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_final
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pts
_database_code_depnum_ccdc_archive 'CCDC 1826576'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_final               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.765 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_final               
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9226 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            diisobutylamine
_chemical_formula_sum            'C8 H19 N'
_chemical_formula_weight         129.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.442(11)
_cell_length_b                   11.612(8)
_cell_length_c                   18.375(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.080(15)
_cell_angle_gamma                90
_cell_volume                     3722(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1046
_cell_measurement_theta_min      4.763
_cell_measurement_theta_max      51.478

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.923
_exptl_crystal_F_000             1184
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            5420
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.107
_diffrn_reflns_theta_max         26.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.738
_diffrn_measured_fraction_theta_full 0.765
_diffrn_reflns_Laue_measured_fraction_max 0.738
_diffrn_reflns_Laue_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_point_group_measured_fraction_full 0.765
_reflns_number_total             2879
_reflns_number_gt                1972
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+7.5963P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     185
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2073
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.10199(16) 0.5776(2) 0.22987(16) 0.0193(7) Uani 1 1 d D . . . .
H1A H 0.118(3) 0.528(4) 0.196(2) 0.004(7) Uiso 0.50(3) 1 d D U P . .
H1B H 0.0536(19) 0.558(4) 0.240(3) 0.004(7) Uiso 0.50(3) 1 d D U P . .
C11 C 0.15035(18) 0.5613(2) 0.29474(16) 0.0183(8) Uani 1 1 d . . . . .
H11A H 0.1336 0.6155 0.3331 0.022 Uiso 1 1 calc R U . . .
H11B H 0.2041 0.5801 0.2823 0.022 Uiso 1 1 calc R U . . .
C12 C 0.14708(18) 0.4389(2) 0.32451(17) 0.0187(8) Uani 1 1 d . . . . .
H12 H 0.1573 0.3849 0.2833 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2103(2) 0.4215(3) 0.38159(19) 0.0290(9) Uani 1 1 d . . . . .
H13A H 0.2604 0.4351 0.3592 0.043 Uiso 1 1 calc R U . . .
H13B H 0.2080 0.3425 0.4002 0.043 Uiso 1 1 calc R U . . .
H13C H 0.2027 0.4758 0.4218 0.043 Uiso 1 1 calc R U . . .
C14 C 0.06923(19) 0.4100(3) 0.35549(19) 0.0261(9) Uani 1 1 d . . . . .
H14A H 0.0698 0.3311 0.3744 0.039 Uiso 1 1 calc R U . . .
H14B H 0.0303 0.4166 0.3172 0.039 Uiso 1 1 calc R U . . .
H14C H 0.0571 0.4636 0.3950 0.039 Uiso 1 1 calc R U . . .
C15 C 0.10349(18) 0.6971(2) 0.20423(16) 0.0180(8) Uani 1 1 d . . . . .
H15A H 0.1573 0.7197 0.1946 0.022 Uiso 1 1 calc R U . . .
H15B H 0.0836 0.7479 0.2432 0.022 Uiso 1 1 calc R U . . .
C16 C 0.05614(18) 0.7161(2) 0.13514(17) 0.0186(8) Uani 1 1 d . . . . .
H16 H 0.0025 0.6899 0.1451 0.022 Uiso 1 1 calc R U . . .
C17 C 0.0863(2) 0.6482(3) 0.07091(18) 0.0297(9) Uani 1 1 d . . . . .
H17A H 0.0838 0.5657 0.0819 0.045 Uiso 1 1 calc R U . . .
H17B H 0.1396 0.6702 0.0614 0.045 Uiso 1 1 calc R U . . .
H17C H 0.0549 0.6647 0.0279 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0536(2) 0.8442(3) 0.11760(19) 0.0290(9) Uani 1 1 d . . . . .
H18A H 0.0322 0.8863 0.1591 0.044 Uiso 1 1 calc R U . . .
H18B H 0.0212 0.8568 0.0747 0.044 Uiso 1 1 calc R U . . .
H18C H 0.1056 0.8719 0.1077 0.044 Uiso 1 1 calc R U . . .
N2 N 0.21463(16) 0.4039(2) 0.12199(16) 0.0199(7) Uani 1 1 d D . . . .
H2A H 0.225(3) 0.424(4) 0.0762(18) 0.004(7) Uiso 0.50(3) 1 d D U P . .
H2B H 0.184(3) 0.459(4) 0.139(2) 0.004(7) Uiso 0.50(3) 1 d D U P . .
C21 C 0.28676(17) 0.4209(2) 0.16213(17) 0.0191(8) Uani 1 1 d . . . . .
H21A H 0.3253 0.3646 0.1448 0.023 Uiso 1 1 calc R U . . .
H21B H 0.2779 0.4063 0.2145 0.023 Uiso 1 1 calc R U . . .
C22 C 0.31811(18) 0.5425(2) 0.15232(17) 0.0199(8) Uani 1 1 d . . . . .
H22 H 0.2760 0.5980 0.1639 0.024 Uiso 1 1 calc R U . . .
C23 C 0.3438(2) 0.5645(3) 0.07436(18) 0.0284(9) Uani 1 1 d . . . . .
H23A H 0.3606 0.6446 0.0695 0.043 Uiso 1 1 calc R U . . .
H23B H 0.3009 0.5502 0.0411 0.043 Uiso 1 1 calc R U . . .
H23C H 0.3863 0.5128 0.0623 0.043 Uiso 1 1 calc R U . . .
C24 C 0.3839(2) 0.5640(3) 0.20594(19) 0.0298(9) Uani 1 1 d . . . . .
H24A H 0.3664 0.5481 0.2556 0.045 Uiso 1 1 calc R U . . .
H24B H 0.4004 0.6444 0.2024 0.045 Uiso 1 1 calc R U . . .
H24C H 0.4270 0.5132 0.1941 0.045 Uiso 1 1 calc R U . . .
C25 C 0.18423(18) 0.2871(2) 0.12667(17) 0.0188(8) Uani 1 1 d . . . . .
H25A H 0.1701 0.2703 0.1777 0.023 Uiso 1 1 calc R U . . .
H25B H 0.2244 0.2317 0.1119 0.023 Uiso 1 1 calc R U . . .
C26 C 0.11399(18) 0.2714(2) 0.07800(17) 0.0204(8) Uani 1 1 d . . . . .
H26 H 0.0768 0.3343 0.0895 0.024 Uiso 1 1 calc R U . . .
C27 C 0.07480(19) 0.1567(3) 0.09286(19) 0.0260(9) Uani 1 1 d . . . . .
H27A H 0.0570 0.1548 0.1434 0.039 Uiso 1 1 calc R U . . .
H27B H 0.1113 0.0938 0.0848 0.039 Uiso 1 1 calc R U . . .
H27C H 0.0309 0.1477 0.0600 0.039 Uiso 1 1 calc R U . . .
C28 C 0.1351(2) 0.2808(3) -0.00226(18) 0.0323(10) Uani 1 1 d . . . . .
H28A H 0.1589 0.3558 -0.0114 0.048 Uiso 1 1 calc R U . . .
H28B H 0.0886 0.2733 -0.0320 0.048 Uiso 1 1 calc R U . . .
H28C H 0.1711 0.2193 -0.0149 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.466(4) . ?
N1 C11 1.472(4) . ?
C11 C12 1.523(4) . ?
C12 C14 1.511(5) . ?
C12 C13 1.534(4) . ?
C15 C16 1.529(4) . ?
C16 C17 1.514(5) . ?
C16 C18 1.522(4) . ?
N2 C25 1.458(4) . ?
N2 C21 1.471(4) . ?
C21 C22 1.525(4) . ?
C22 C23 1.523(5) . ?
C22 C24 1.532(4) . ?
C25 C26 1.527(4) . ?
C26 C27 1.522(4) . ?
C26 C28 1.524(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C11 111.9(2) . . ?
N1 C11 C12 112.9(2) . . ?
C14 C12 C11 112.1(3) . . ?
C14 C12 C13 111.0(3) . . ?
C11 C12 C13 110.0(2) . . ?
N1 C15 C16 113.2(2) . . ?
C17 C16 C18 110.7(3) . . ?
C17 C16 C15 112.6(3) . . ?
C18 C16 C15 109.4(2) . . ?
C25 N2 C21 113.9(2) . . ?
N2 C21 C22 111.8(2) . . ?
C23 C22 C21 111.9(3) . . ?
C23 C22 C24 110.9(3) . . ?
C21 C22 C24 110.1(2) . . ?
N2 C25 C26 111.6(2) . . ?
C27 C26 C28 110.2(3) . . ?
C27 C26 C25 111.1(2) . . ?
C28 C26 C25 111.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.89(3) 2.60(3) 3.446(4) 158(4) .
N1 H1B N1 0.89(3) 2.78(3) 3.635(6) 161(4) 2
N2 H2B N1 0.89(3) 2.59(3) 3.446(4) 160(4) .

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.054



_chemical_name_systematic        diisobutylamine
_chemical_formula_moiety         'C8 H19 N'
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DiIsoProAmine_30s_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pvt
_database_code_depnum_ccdc_archive 'CCDC 1826577'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_DiIsoProAmine_30s_0m 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.932 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_DiIsoProAmine_30s_0m 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9276 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            diisopropylamine
_chemical_formula_sum            'C6 H15 N'
_chemical_formula_weight         101.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.527(8)
_cell_length_b                   7.293(4)
_cell_length_c                   14.148(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.794(11)
_cell_angle_gamma                90
_cell_volume                     1449.4(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2063
_cell_measurement_theta_min      5.801
_cell_measurement_theta_max      52.603

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.927
_exptl_crystal_F_000             464
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            6124
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             1359
_reflns_number_gt                1108
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1359
_refine_ls_number_parameters     76
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.07016(7) 0.01136(13) 0.36988(8) 0.0222(3) Uani 1 1 d D . . . .
H1A H 0.0336(14) 0.006(3) 0.3129(14) 0.010(4) Uiso 0.487(18) 1 d D U P . .
H1B H 0.0367(14) -0.048(3) 0.3986(15) 0.010(4) Uiso 0.513(18) 1 d D U P . .
C1 C 0.07850(7) 0.20185(14) 0.40561(8) 0.0209(3) Uani 1 1 d . . . . .
H1 H 0.1186 0.2719 0.3702 0.025 Uiso 1 1 calc R U . . .
C2 C -0.02093(8) 0.28654(16) 0.38107(9) 0.0266(3) Uani 1 1 d . . . . .
H2A H -0.0486 0.2813 0.3103 0.040 Uiso 1 1 calc R U . . .
H2B H -0.0166 0.4146 0.4027 0.040 Uiso 1 1 calc R U . . .
H2C H -0.0614 0.2181 0.4145 0.040 Uiso 1 1 calc R U . . .
C3 C 0.12406(8) 0.21576(16) 0.51502(9) 0.0288(3) Uani 1 1 d . . . . .
H3A H 0.0845 0.1508 0.5509 0.043 Uiso 1 1 calc R U . . .
H3B H 0.1294 0.3450 0.5346 0.043 Uiso 1 1 calc R U . . .
H3C H 0.1876 0.1604 0.5300 0.043 Uiso 1 1 calc R U . . .
C4 C 0.15993(8) -0.08684(14) 0.37409(9) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.2038 -0.0682 0.4404 0.028 Uiso 1 1 calc R U . . .
C5 C 0.20909(8) -0.01723(16) 0.29781(9) 0.0267(3) Uani 1 1 d . . . . .
H5A H 0.1682 -0.0402 0.2322 0.040 Uiso 1 1 calc R U . . .
H5B H 0.2698 -0.0815 0.3055 0.040 Uiso 1 1 calc R U . . .
H5C H 0.2208 0.1147 0.3067 0.040 Uiso 1 1 calc R U . . .
C6 C 0.13827(10) -0.29084(16) 0.35993(11) 0.0378(4) Uani 1 1 d . . . . .
H6A H 0.1092 -0.3345 0.4111 0.057 Uiso 1 1 calc R U . . .
H6B H 0.1975 -0.3582 0.3639 0.057 Uiso 1 1 calc R U . . .
H6C H 0.0942 -0.3111 0.2957 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4728(15) . ?
N1 C4 1.4757(15) . ?
C1 C3 1.5237(18) . ?
C1 C2 1.5272(16) . ?
C4 C6 1.5233(17) . ?
C4 C5 1.5251(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 116.71(9) . . ?
N1 C1 C3 112.82(9) . . ?
N1 C1 C2 108.26(9) . . ?
C3 C1 C2 110.14(9) . . ?
N1 C4 C6 108.54(9) . . ?
N1 C4 C5 112.24(10) . . ?
C6 C4 C5 110.51(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N1 0.845(18) 2.641(19) 3.483(3) 175(2) 2

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.031



_chemical_name_systematic        diisopropylamine
_chemical_formula_moiety         'C6 H15 N'
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DPA100KThirdONETWOTHREE_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9q11
_database_code_depnum_ccdc_archive 'CCDC 1826583'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_DPA100KThirdONETWOTHREE_0m 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.887 Why?
RESPONSE: The experimental setup required that the capillary was always kept in a vertical alignment, which limited the coverage of reflections
;
_vrf_PLAT049_DPA100KThirdONETWOTHREE_0m 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9030 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            dipropylamine
_chemical_formula_sum            'C6 H15 N'
_chemical_formula_weight         101.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.158(2)
_cell_length_b                   10.492(3)
_cell_length_c                   26.090(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.156(4)
_cell_angle_gamma                90
_cell_volume                     2233.3(10)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5522
_cell_measurement_theta_min      4.983
_cell_measurement_theta_max      52.822

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.903
_exptl_crystal_F_000             696
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            17101
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.092
_diffrn_reflns_theta_max         26.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.887
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.887
_reflns_number_total             3999
_reflns_number_gt                3148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.9295P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3999
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.03842(18) 0.41353(11) 0.40073(4) 0.0232(3) Uani 1 1 d . . . . .
H1 H 0.117(2) 0.4252(15) 0.3815(6) 0.024(4) Uiso 1 1 d . . . . .
C11 C 0.0865(2) 0.31488(13) 0.43731(5) 0.0236(3) Uani 1 1 d . . . . .
H11A H -0.0060 0.2974 0.4608 0.028 Uiso 1 1 calc R U . . .
H11B H 0.1800 0.3458 0.4581 0.028 Uiso 1 1 calc R U . . .
C12 C 0.1347(2) 0.19302(13) 0.41024(5) 0.0265(4) Uani 1 1 d . . . . .
H12A H 0.2304 0.2101 0.3880 0.032 Uiso 1 1 calc R U . . .
H12B H 0.0430 0.1652 0.3880 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1773(2) 0.08613(14) 0.44729(6) 0.0361(4) Uani 1 1 d . . . . .
H13A H 0.2077 0.0097 0.4279 0.054 Uiso 1 1 calc R U . . .
H13B H 0.0821 0.0673 0.4688 0.054 Uiso 1 1 calc R U . . .
H13C H 0.2695 0.1125 0.4690 0.054 Uiso 1 1 calc R U . . .
C14 C 0.0004(2) 0.53395(13) 0.42625(5) 0.0245(3) Uani 1 1 d . . . . .
H14A H 0.0980 0.5634 0.4455 0.029 Uiso 1 1 calc R U . . .
H14B H -0.0892 0.5200 0.4511 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0509(2) 0.63656(13) 0.38826(5) 0.0259(4) Uani 1 1 d . . . . .
H15A H 0.0284 0.6389 0.3596 0.031 Uiso 1 1 calc R U . . .
H15B H -0.1599 0.6150 0.3739 0.031 Uiso 1 1 calc R U . . .
C16 C -0.0586(2) 0.76719(15) 0.41325(6) 0.0374(4) Uani 1 1 d . . . . .
H16A H -0.0948 0.8303 0.3879 0.056 Uiso 1 1 calc R U . . .
H16B H 0.0503 0.7905 0.4261 0.056 Uiso 1 1 calc R U . . .
H16C H -0.1364 0.7651 0.4418 0.056 Uiso 1 1 calc R U . . .
N2 N 0.37957(18) 0.47479(11) 0.34541(5) 0.0255(3) Uani 1 1 d . . . . .
H2 H 0.469(2) 0.4288(16) 0.3469(6) 0.027(4) Uiso 1 1 d . . . . .
C21 C 0.4194(2) 0.59756(13) 0.36843(6) 0.0284(4) Uani 1 1 d . . . . .
H21A H 0.3218 0.6536 0.3671 0.034 Uiso 1 1 calc R U . . .
H21B H 0.5078 0.6388 0.3485 0.034 Uiso 1 1 calc R U . . .
C22 C 0.4744(2) 0.58225(15) 0.42376(6) 0.0321(4) Uani 1 1 d . . . . .
H22A H 0.5828 0.5399 0.4244 0.038 Uiso 1 1 calc R U . . .
H22B H 0.3958 0.5263 0.4419 0.038 Uiso 1 1 calc R U . . .
C23 C 0.4866(3) 0.70838(17) 0.45212(8) 0.0496(5) Uani 1 1 d . . . . .
H23A H 0.5313 0.6938 0.4865 0.074 Uiso 1 1 calc R U . . .
H23B H 0.3773 0.7465 0.4549 0.074 Uiso 1 1 calc R U . . .
H23C H 0.5590 0.7662 0.4333 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3302(2) 0.48293(14) 0.29167(5) 0.0275(4) Uani 1 1 d . . . . .
H24A H 0.4227 0.5159 0.2711 0.033 Uiso 1 1 calc R U . . .
H24B H 0.2375 0.5432 0.2882 0.033 Uiso 1 1 calc R U . . .
C25 C 0.2794(2) 0.35322(14) 0.27156(6) 0.0308(4) Uani 1 1 d . . . . .
H25A H 0.1783 0.3258 0.2893 0.037 Uiso 1 1 calc R U . . .
H25B H 0.3665 0.2906 0.2797 0.037 Uiso 1 1 calc R U . . .
C26 C 0.2487(3) 0.35301(17) 0.21412(6) 0.0433(5) Uani 1 1 d . . . . .
H26A H 0.2105 0.2685 0.2034 0.065 Uiso 1 1 calc R U . . .
H26B H 0.3507 0.3735 0.1962 0.065 Uiso 1 1 calc R U . . .
H26C H 0.1652 0.4168 0.2057 0.065 Uiso 1 1 calc R U . . .
N3 N 0.71949(18) 0.32524(11) 0.33233(5) 0.0252(3) Uani 1 1 d . . . . .
H3 H 0.804(2) 0.3565(15) 0.3494(6) 0.024(4) Uiso 1 1 d . . . . .
C31 C 0.7546(2) 0.32676(14) 0.27747(6) 0.0290(4) Uani 1 1 d . . . . .
H31A H 0.6578 0.2949 0.2585 0.035 Uiso 1 1 calc R U . . .
H31B H 0.8474 0.2686 0.2704 0.035 Uiso 1 1 calc R U . . .
C32 C 0.7971(2) 0.45909(15) 0.25848(6) 0.0342(4) Uani 1 1 d . . . . .
H32A H 0.9073 0.4829 0.2713 0.041 Uiso 1 1 calc R U . . .
H32B H 0.7173 0.5209 0.2725 0.041 Uiso 1 1 calc R U . . .
C33 C 0.7953(3) 0.4672(2) 0.20005(7) 0.0534(6) Uani 1 1 d . . . . .
H33A H 0.8332 0.5516 0.1893 0.080 Uiso 1 1 calc R U . . .
H33B H 0.6835 0.4532 0.1874 0.080 Uiso 1 1 calc R U . . .
H33C H 0.8681 0.4018 0.1859 0.080 Uiso 1 1 calc R U . . .
C34 C 0.6864(2) 0.19727(13) 0.35147(6) 0.0271(4) Uani 1 1 d . . . . .
H34A H 0.7838 0.1428 0.3458 0.033 Uiso 1 1 calc R U . . .
H34B H 0.5936 0.1600 0.3321 0.033 Uiso 1 1 calc R U . . .
C35 C 0.6454(2) 0.19878(14) 0.40799(6) 0.0295(4) Uani 1 1 d . . . . .
H35A H 0.5410 0.2452 0.4131 0.035 Uiso 1 1 calc R U . . .
H35B H 0.7323 0.2454 0.4268 0.035 Uiso 1 1 calc R U . . .
C36 C 0.6296(3) 0.06537(16) 0.43015(7) 0.0480(5) Uani 1 1 d . . . . .
H36A H 0.5989 0.0710 0.4664 0.072 Uiso 1 1 calc R U . . .
H36B H 0.7346 0.0208 0.4271 0.072 Uiso 1 1 calc R U . . .
H36C H 0.5450 0.0183 0.4113 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.4606(18) . ?
N1 C14 1.4619(18) . ?
C11 C12 1.5132(19) . ?
C12 C13 1.520(2) . ?
C14 C15 1.5214(19) . ?
C15 C16 1.519(2) . ?
N2 C21 1.4576(19) . ?
N2 C24 1.4604(19) . ?
C21 C22 1.519(2) . ?
C22 C23 1.519(2) . ?
C24 C25 1.516(2) . ?
C25 C26 1.519(2) . ?
N3 C34 1.4580(18) . ?
N3 C31 1.4606(19) . ?
C31 C32 1.515(2) . ?
C32 C33 1.527(2) . ?
C34 C35 1.513(2) . ?
C35 C36 1.520(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C14 111.83(11) . . ?
N1 C11 C12 111.32(11) . . ?
C11 C12 C13 112.69(12) . . ?
N1 C14 C15 111.91(11) . . ?
C16 C15 C14 111.75(12) . . ?
C21 N2 C24 113.86(12) . . ?
N2 C21 C22 111.28(12) . . ?
C21 C22 C23 112.92(14) . . ?
N2 C24 C25 110.75(12) . . ?
C24 C25 C26 112.77(13) . . ?
C34 N3 C31 112.50(11) . . ?
N3 C31 C32 112.10(12) . . ?
C31 C32 C33 112.08(14) . . ?
N3 C34 C35 111.45(12) . . ?
C34 C35 C36 112.35(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.824(18) 2.400(19) 3.204(2) 165.2(15) .
N2 H2 N3 0.878(18) 2.344(19) 3.205(2) 166.9(14) .
N3 H3 N1 0.886(18) 2.405(18) 3.285(2) 172.4(14) 1_655

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033



_chemical_name_systematic        dipropylamine
_chemical_formula_moiety         'C6 H15 N'
_chemical_melting_point          210
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_EtMeNH_100K-60s_x
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pxw
_database_code_depnum_ccdc_archive 'CCDC 1826579'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            methylethylamine
_chemical_formula_sum            'C3 H9 N'
_chemical_formula_weight         59.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.761(5)
_cell_length_b                   16.084(13)
_cell_length_c                   14.231(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.851(10)
_cell_angle_gamma                90
_cell_volume                     1750(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1032
_cell_measurement_theta_min      5.065
_cell_measurement_theta_max      48.080

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.897
_exptl_crystal_F_000             544
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4595
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            4327
_diffrn_reflns_av_unetI/netI     0.1143
_diffrn_reflns_av_R_equivalents  0.1288
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.927
_diffrn_reflns_theta_max         24.681
_diffrn_reflns_theta_full        24.681
_diffrn_measured_fraction_theta_max 0.772
_diffrn_measured_fraction_theta_full 0.772
_diffrn_reflns_Laue_measured_fraction_max 0.772
_diffrn_reflns_Laue_measured_fraction_full 0.772
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_point_group_measured_fraction_full 0.772
_reflns_number_total             2292
_reflns_number_gt                1428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2292
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1810
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.8543(3) 0.06137(12) 0.72199(13) 0.0257(6) Uani 1 1 d . . . . .
H1 H -0.814(3) 0.1101(16) 0.7319(16) 0.033(7) Uiso 1 1 d . . . . .
C11 C -0.8499(4) 0.03267(16) 0.62463(16) 0.0370(8) Uani 1 1 d . . . . .
H11A H -0.7284 0.0228 0.6171 0.056 Uiso 1 1 calc R U . . .
H11B H -0.9016 0.0752 0.5790 0.056 Uiso 1 1 calc R U . . .
H11C H -0.9167 -0.0191 0.6127 0.056 Uiso 1 1 calc R U . . .
C12 C -0.7637(4) 0.00324(15) 0.79248(16) 0.0320(7) Uani 1 1 d . . . . .
H12A H -0.6432 -0.0057 0.7803 0.038 Uiso 1 1 calc R U . . .
H12B H -0.8250 -0.0510 0.7859 0.038 Uiso 1 1 calc R U . . .
C13 C -0.7564(4) 0.03546(16) 0.89298(16) 0.0433(8) Uani 1 1 d . . . . .
H13A H -0.6924 0.0883 0.9003 0.065 Uiso 1 1 calc R U . . .
H13B H -0.6964 -0.0052 0.9385 0.065 Uiso 1 1 calc R U . . .
H13C H -0.8755 0.0442 0.9052 0.065 Uiso 1 1 calc R U . . .
N2 N -0.7455(3) 0.25381(13) 0.74253(14) 0.0298(7) Uani 1 1 d . . . . .
H2 H -0.651(4) 0.2811(17) 0.7326(17) 0.038(8) Uiso 1 1 d . . . . .
C21 C -0.7782(4) 0.27195(16) 0.84016(16) 0.0349(7) Uani 1 1 d . . . . .
H21A H -0.8045 0.3312 0.8454 0.052 Uiso 1 1 calc R U . . .
H21B H -0.6740 0.2578 0.8867 0.052 Uiso 1 1 calc R U . . .
H21C H -0.8777 0.2388 0.8529 0.052 Uiso 1 1 calc R U . . .
C22 C -0.8905(4) 0.28187(15) 0.67131(17) 0.0330(7) Uani 1 1 d . . . . .
H22A H -0.9200 0.3400 0.6850 0.040 Uiso 1 1 calc R U . . .
H22B H -0.9944 0.2469 0.6743 0.040 Uiso 1 1 calc R U . . .
C23 C -0.8445(4) 0.27682(18) 0.57314(17) 0.0450(8) Uani 1 1 d . . . . .
H23A H -0.7465 0.3143 0.5690 0.068 Uiso 1 1 calc R U . . .
H23B H -0.9459 0.2932 0.5259 0.068 Uiso 1 1 calc R U . . .
H23C H -0.8110 0.2197 0.5606 0.068 Uiso 1 1 calc R U . . .
N3 N -0.3720(3) 0.32958(12) 0.70088(13) 0.0261(6) Uani 1 1 d . . . . .
H3 H -0.316(4) 0.2810(16) 0.7108(16) 0.035(7) Uiso 1 1 d . . . . .
C31 C -0.3701(4) 0.35400(17) 0.60163(16) 0.0388(8) Uani 1 1 d . . . . .
H31A H -0.4377 0.4053 0.5872 0.058 Uiso 1 1 calc R U . . .
H31B H -0.4223 0.3097 0.5587 0.058 Uiso 1 1 calc R U . . .
H31C H -0.2492 0.3633 0.5927 0.058 Uiso 1 1 calc R U . . .
C32 C -0.2856(4) 0.39182(15) 0.76756(16) 0.0308(7) Uani 1 1 d . . . . .
H32A H -0.3523 0.4445 0.7587 0.037 Uiso 1 1 calc R U . . .
H32B H -0.1667 0.4026 0.7540 0.037 Uiso 1 1 calc R U . . .
C33 C -0.2731(4) 0.36282(16) 0.86966(16) 0.0369(8) Uani 1 1 d . . . . .
H33A H -0.3903 0.3496 0.8823 0.055 Uiso 1 1 calc R U . . .
H33B H -0.2216 0.4070 0.9130 0.055 Uiso 1 1 calc R U . . .
H33C H -0.1992 0.3131 0.8798 0.055 Uiso 1 1 calc R U . . .
N4 N -0.2395(4) 0.13949(13) 0.73932(14) 0.0302(6) Uani 1 1 d . . . . .
H4 H -0.147(4) 0.1154(16) 0.7337(16) 0.029(8) Uiso 1 1 d . . . . .
C41 C -0.2785(4) 0.12494(16) 0.83686(16) 0.0366(8) Uani 1 1 d . . . . .
H41A H -0.3851 0.1551 0.8443 0.055 Uiso 1 1 calc R U . . .
H41B H -0.1806 0.1449 0.8843 0.055 Uiso 1 1 calc R U . . .
H41C H -0.2955 0.0653 0.8462 0.055 Uiso 1 1 calc R U . . .
C42 C -0.3774(4) 0.10843(16) 0.66635(17) 0.0376(8) Uani 1 1 d . . . . .
H42A H -0.4846 0.1419 0.6658 0.045 Uiso 1 1 calc R U . . .
H42B H -0.4041 0.0501 0.6806 0.045 Uiso 1 1 calc R U . . .
C43 C -0.3223(4) 0.11302(18) 0.57005(17) 0.0443(8) Uani 1 1 d . . . . .
H43A H -0.2830 0.1696 0.5592 0.066 Uiso 1 1 calc R U . . .
H43B H -0.4217 0.0987 0.5204 0.066 Uiso 1 1 calc R U . . .
H43C H -0.2264 0.0738 0.5678 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.461(3) . ?
N1 C11 1.466(3) . ?
C12 C13 1.513(3) . ?
N2 C22 1.452(3) . ?
N2 C21 1.483(3) . ?
C22 C23 1.502(4) . ?
N3 C32 1.461(3) . ?
N3 C31 1.469(3) . ?
C32 C33 1.513(3) . ?
N4 C42 1.446(3) . ?
N4 C41 1.489(3) . ?
C42 C43 1.505(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C11 111.2(2) . . ?
N1 C12 C13 111.5(2) . . ?
C22 N2 C21 110.9(2) . . ?
N2 C22 C23 110.7(2) . . ?
C32 N3 C31 111.3(2) . . ?
N3 C32 C33 111.1(2) . . ?
C42 N4 C41 111.8(2) . . ?
N4 C42 C43 110.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.85(3) 2.37(3) 3.209(4) 170(2) .
N2 H2 N3 0.89(3) 2.41(3) 3.290(4) 169(2) .
N3 H3 N4 0.89(3) 2.37(3) 3.242(4) 165(2) .
N4 H4 N1 0.83(3) 2.46(3) 3.291(4) 173(3) 1_655

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.069



_chemical_name_systematic        methylethylamine
_chemical_formula_moiety         'C3 H9 N'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_diethylamine_30s_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pyx
_database_code_depnum_ccdc_archive 'CCDC 1826580'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
_audit_update_record             
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT049_diethylamine_30s_0m 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9067 Check
RESPONSE: Small organic molecule compound of low density
;
# Added during the CSD deposition process: Wednesday 28 February 2018 01:20 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            diethylamine
_chemical_formula_sum            'C4 H11 N'
_chemical_formula_weight         73.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.989(2)
_cell_length_b                   15.320(5)
_cell_length_c                   13.213(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.290(5)
_cell_angle_gamma                90
_cell_volume                     1607.5(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8753
_cell_measurement_theta_min      5.318
_cell_measurement_theta_max      52.675

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.907
_exptl_crystal_F_000             504
_exptl_crystal_size_rad          0.25
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   sealed-tube
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_reflns_number            26561
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3200
_reflns_number_gt                2732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex'
_computing_cell_refinement       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0222P)²+1.8140P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3200
_refine_ls_number_parameters     162
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.98340(18) 0.34873(9) 0.74867(10) 0.0213(3) Uani 1 1 d D . . . .
H1A H 1.059(3) 0.3845(17) 0.738(2) 0.009(3) Uiso 0.495(14) 1 d D U P . .
H1B H 0.912(3) 0.3765(17) 0.778(2) 0.009(3) Uiso 0.505(14) 1 d D U P . .
C11 C 1.0536(2) 0.28226(10) 0.82052(13) 0.0250(4) Uani 1 1 d . . . . .
H11A H 1.1422 0.2492 0.7902 0.030 Uiso 1 1 calc R U . . .
H11B H 0.9640 0.2408 0.8345 0.030 Uiso 1 1 calc R U . . .
C12 C 1.1280(2) 0.32408(12) 0.91937(13) 0.0285(4) Uani 1 1 d . . . . .
H12A H 1.2173 0.3649 0.9055 0.043 Uiso 1 1 calc R U . . .
H12B H 1.1752 0.2787 0.9664 0.043 Uiso 1 1 calc R U . . .
H12C H 1.0397 0.3557 0.9501 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9102(2) 0.31255(11) 0.65174(12) 0.0255(4) Uani 1 1 d . . . . .
H13A H 0.8143 0.2741 0.6630 0.031 Uiso 1 1 calc R U . . .
H13B H 0.9954 0.2770 0.6214 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8498(2) 0.38588(12) 0.57928(13) 0.0292(4) Uani 1 1 d . . . . .
H14A H 0.7666 0.4214 0.6099 0.044 Uiso 1 1 calc R U . . .
H14B H 0.7981 0.3610 0.5150 0.044 Uiso 1 1 calc R U . . .
H14C H 0.9457 0.4225 0.5662 0.044 Uiso 1 1 calc R U . . .
N2 N 1.30515(19) 0.45517(9) 0.69740(10) 0.0223(3) Uani 1 1 d D . . . .
H2A H 1.391(3) 0.447(2) 0.739(2) 0.009(3) Uiso 0.495(14) 1 d D U P . .
H2B H 1.232(3) 0.4198(17) 0.713(2) 0.009(3) Uiso 0.505(14) 1 d D U P . .
C21 C 1.3428(2) 0.43399(11) 0.59449(12) 0.0266(4) Uani 1 1 d . . . . .
H21A H 1.4366 0.4712 0.5767 0.032 Uiso 1 1 calc R U . . .
H21B H 1.2429 0.4467 0.5455 0.032 Uiso 1 1 calc R U . . .
C22 C 1.3908(2) 0.33874(12) 0.58562(14) 0.0317(4) Uani 1 1 d . . . . .
H22A H 1.4903 0.3261 0.6336 0.048 Uiso 1 1 calc R U . . .
H22B H 1.4162 0.3267 0.5161 0.048 Uiso 1 1 calc R U . . .
H22C H 1.2969 0.3018 0.6014 0.048 Uiso 1 1 calc R U . . .
C23 C 1.2513(2) 0.54567(11) 0.70614(13) 0.0263(4) Uani 1 1 d . . . . .
H23A H 1.1433 0.5546 0.6630 0.032 Uiso 1 1 calc R U . . .
H23B H 1.3362 0.5849 0.6811 0.032 Uiso 1 1 calc R U . . .
C24 C 1.2295(2) 0.56872(12) 0.81559(13) 0.0315(4) Uani 1 1 d . . . . .
H24A H 1.1452 0.5301 0.8404 0.047 Uiso 1 1 calc R U . . .
H24B H 1.1920 0.6294 0.8191 0.047 Uiso 1 1 calc R U . . .
H24C H 1.3372 0.5615 0.8580 0.047 Uiso 1 1 calc R U . . .
N3 N 1.6552(2) 0.41360(9) 0.84249(11) 0.0252(3) Uani 1 1 d D . . . .
H3A H 1.726(3) 0.3921(19) 0.807(2) 0.009(3) Uiso 0.495(14) 1 d D U P . .
H3B H 1.570(3) 0.426(2) 0.8024(19) 0.009(3) Uiso 0.505(14) 1 d D U P . .
C31 C 1.7153(2) 0.49571(11) 0.89010(14) 0.0301(4) Uani 1 1 d . . . . .
H31A H 1.8223 0.4853 0.9337 0.036 Uiso 1 1 calc R U . . .
H31B H 1.6317 0.5178 0.9339 0.036 Uiso 1 1 calc R U . . .
C32 C 1.7431(3) 0.56336(12) 0.81016(16) 0.0375(5) Uani 1 1 d . . . . .
H32A H 1.8269 0.5418 0.7674 0.056 Uiso 1 1 calc R U . . .
H32B H 1.7835 0.6177 0.8436 0.056 Uiso 1 1 calc R U . . .
H32C H 1.6367 0.5744 0.7678 0.056 Uiso 1 1 calc R U . . .
C33 C 1.6237(2) 0.34698(12) 0.91742(13) 0.0270(4) Uani 1 1 d . . . . .
H33A H 1.5370 0.3684 0.9594 0.032 Uiso 1 1 calc R U . . .
H33B H 1.7284 0.3363 0.9631 0.032 Uiso 1 1 calc R U . . .
C34 C 1.5647(2) 0.26219(12) 0.86626(14) 0.0314(4) Uani 1 1 d . . . . .
H34A H 1.4583 0.2720 0.8234 0.047 Uiso 1 1 calc R U . . .
H34B H 1.5479 0.2184 0.9183 0.047 Uiso 1 1 calc R U . . .
H34C H 1.6498 0.2413 0.8240 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.458(2) . ?
N1 C11 1.462(2) . ?
C11 C12 1.516(2) . ?
C13 C14 1.520(2) . ?
N2 C23 1.460(2) . ?
N2 C21 1.461(2) . ?
C21 C22 1.517(2) . ?
C23 C24 1.517(2) . ?
N3 C33 1.463(2) . ?
N3 C31 1.464(2) . ?
C31 C32 1.513(3) . ?
C33 C34 1.515(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C11 113.22(13) . . ?
N1 C11 C12 110.57(14) . . ?
N1 C13 C14 109.97(14) . . ?
C23 N2 C21 112.15(13) . . ?
N2 C21 C22 111.42(14) . . ?
N2 C23 C24 111.22(14) . . ?
C33 N3 C31 112.42(14) . . ?
N3 C31 C32 110.78(15) . . ?
N3 C33 C34 111.36(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.841(18) 2.355(18) 3.179(2) 167(3) .
N1 H1B N3 0.836(17) 2.378(18) 3.180(2) 161(3) 1_455
N2 H2A N3 0.840(18) 2.441(18) 3.275(2) 173(3) .
N2 H2B N1 0.842(17) 2.355(18) 3.179(2) 166(3) .
N3 H3A N1 0.838(18) 2.371(18) 3.180(2) 162(3) 1_655
N3 H3B N2 0.836(18) 2.443(18) 3.275(2) 174(3) .

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037



_chemical_name_systematic        diethylamine
_chemical_formula_moiety         'C4 H11 N'
_chemical_melting_point          223
