#------------------------------------------------------------------------------
#$Date: 2019-11-17 05:09:45 +0100 (Sun 17 de Nov de 2019) $
#$Revision: 228328 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/17/7121736.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7121736
loop_
_publ_author_name
'Hanke, Felix'
'Pugh, Chloe J.'
'Kay, Ellis F.'
'Taylor, Joshua B.'
'Todd, Stephen M.'
'Robertson, Craig M.'
'Slater, Benjamin J.'
'Steiner, Alexander'
_publ_section_title
;
 The simplest supramolecular helix.
;
_journal_issue                   47
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6012
_journal_page_last               6015
_journal_paper_doi               10.1039/c8cc03295e
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C4 H11 N'
_chemical_formula_sum            'C4 H11 N'
_chemical_formula_weight         73.14
_chemical_melting_point          223
_chemical_name_common            diethylamine
_chemical_name_systematic        diethylamine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_block_doi                 10.5517/ccdc.csd.cc1z9pyx
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-02-28 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.290(5)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   7.989(2)
_cell_length_b                   15.320(5)
_cell_length_c                   13.213(4)
_cell_measurement_reflns_used    8753
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      52.675
_cell_measurement_theta_min      5.318
_cell_volume                     1607.4(8)
_computing_cell_refinement       'Bruker Apex'
_computing_data_collection       'Bruker Apex'
_computing_data_reduction        'Bruker Apex'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26561
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.042
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.907
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             504
_exptl_crystal_size_rad          0.25
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0503
_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)+(0.0222P)²+1.8140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc03295e2.cif
_cod_data_source_block           diethylamine_30s_0m
_cod_depositor_comments
'Adding full bibliography for 7121726--7121736.cif.'
_cod_original_cell_volume        1607.5(8)
_cod_database_code               7121736
_shelx_shelxl_version_number     2014/7
_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'
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
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 .
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_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8CC03295E 2018
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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) .
