#------------------------------------------------------------------------------
#$Date: 2021-12-15 05:09:00 +0200 (Wed, 15 Dec 2021) $
#$Revision: 271439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/39/2243950.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243950
loop_
_publ_author_name
'Schrimpf, Tobias'
'Otte, Felix'
'Strohmann, Carsten'
_publ_section_title
;
 Crystal structure of
 N,N,N',N'-tetramethylethanediamine
;
_journal_coeditor_code           HB8002
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021012457
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C6 H16 N2'
_chemical_formula_moiety         'C6 H16 N2'
_chemical_formula_sum            'C6 H16 N2'
_chemical_formula_weight         116.21
_chemical_name_common
;
N,N,N',N'-Tetramethylethanediamine
;
_chemical_name_systematic
;
N,N,N',N'-Tetramethylethane-1,2-diamine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.954(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6987(13)
_cell_length_b                   8.311(2)
_cell_length_c                   8.453(2)
_cell_measurement_reflns_used    352
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      22.83
_cell_measurement_theta_min      3.52
_cell_volume                     382.95(16)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker D8 VENTURE area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16732
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.306
_diffrn_reflns_theta_min         3.516
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.5670
_exptl_absorpt_correction_T_min  0.3707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_description       block
_exptl_crystal_F_000             132
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.304
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     39
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0452P)²+0.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                1434
_reflns_number_total             1720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8002sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        382.92(18)
_cod_database_code               2243950
_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.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.981
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.25269(10) 0.34528(6) 0.53636(6) 0.01749(12) Uani d 1 . .
C C1 0.49338(12) 0.33807(9) 0.65977(9) 0.02394(15) Uani d 1 . .
H H1A 0.5794 0.4404 0.6608 0.036 Uiso calc 1 . .
H H1B 0.5896 0.2505 0.6320 0.036 Uiso calc 1 . .
H H1C 0.4725 0.3185 0.7692 0.036 Uiso calc 1 . .
C C2 0.12526(13) 0.19303(8) 0.53563(9) 0.02363(14) Uani d 1 . .
H H2A 0.0976 0.1764 0.6436 0.035 Uiso calc 1 . .
H H2B 0.2253 0.1048 0.5134 0.035 Uiso calc 1 . .
H H2C -0.0328 0.1955 0.4494 0.035 Uiso calc 1 . .
C C3 0.11367(10) 0.48144(7) 0.57161(7) 0.01782(13) Uani d 1 . .
H H3A 0.2207 0.5776 0.5952 0.021 Uiso calc 1 . .
H H3B 0.0631 0.4573 0.6716 0.021 Uiso calc 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C1 . . 109.26(5) ?
C2 N1 C3 . . 111.96(5) ?
C3 N1 C1 . . 109.75(5) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2B . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 C3 . 3_566 112.37(6) ?
N1 C3 H3A . . 109.1 ?
N1 C3 H3B . . 109.1 ?
C3 C3 H3A 3_566 . 109.1 ?
C3 C3 H3B 3_566 . 109.1 ?
H3A C3 H3B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.4624(9) ?
N1 C2 . 1.4580(9) ?
N1 C3 . 1.4610(8) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 C3 3_566 1.5246(12) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 C3 C3 . . . 3_566 167.33(6) ?
C2 N1 C3 C3 . . . 3_566 -71.17(8) ?
N1 C3 C3 N1 . . 3_566 3_566 180.0 ?

_cod_database_fobs_code 2243950
