#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:42:54 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262553 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/20/7242091.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_7242091
loop_
_publ_author_name
'Renier, Olivier'
'Bousrez, Guillaume'
'Yang, Mei'
'Hölter, Milena'
'Mallick, Bert'
'Smetana, Volodymyr'
'Mudring, Anja-Verena'
_publ_section_title
;
 Developing design tools for introducing and tuning structural order in
 ionic liquids
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1785
_journal_page_last               1795
_journal_paper_doi               10.1039/D0CE01672A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_sum            'C16 H31 Br N2'
_chemical_formula_weight         331.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-04-27 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                83.84(3)
_cell_angle_beta                 78.78(3)
_cell_angle_gamma                79.10(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9890(14)
_cell_length_b                   8.3080(17)
_cell_length_c                   16.476(3)
_cell_measurement_reflns_used    7592
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.098
_cell_measurement_theta_min      2.886
_cell_volume                     919.0(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'STOE IPDS I'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.902
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7592
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.098
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         2.886
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-Red, X-Shape'
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.078(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0627
_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)+(0.1047P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2052
_reflns_number_total             2953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01672a2.cif
_cod_data_source_block           M14H
_cod_depositor_comments
'Adding full bibliography for 7242091--7242093.cif.'
_cod_database_code               7242091
_shelx_shelxl_version_number     2018/3
_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'
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
C1 C -0.6827(11) 1.4558(7) 0.1223(5) 0.0482(16) Uani 1 1 d . . . . .
H1 H -0.803656 1.523886 0.137474 0.058 Uiso 1 1 calc R U . . .
C2 C -0.4486(10) 1.2739(6) 0.0538(4) 0.0388(14) Uani 1 1 d . . . . .
C3 C -0.5237(11) 1.4385(7) 0.1594(5) 0.0478(16) Uani 1 1 d . . . . .
H3 H -0.513406 1.491972 0.204731 0.057 Uiso 1 1 calc R U . . .
N3 N -0.6337(8) 1.3541(6) 0.0575(4) 0.0422(13) Uani 1 1 d . . . . .
H3A H -0.711363 1.344007 0.024477 0.051 Uiso 1 1 calc R U . . .
C4 C -0.3423(10) 1.1554(7) -0.0069(5) 0.0458(16) Uani 1 1 d . . . . .
H4A H -0.423422 1.150341 -0.047049 0.069 Uiso 1 1 calc R U . . .
H4B H -0.313283 1.048784 0.021230 0.069 Uiso 1 1 calc R U . . .
H4C H -0.220990 1.189919 -0.034458 0.069 Uiso 1 1 calc R U . . .
C5 C -0.1763(10) 1.2730(7) 0.1332(5) 0.0470(16) Uani 1 1 d . . . . .
H5A H -0.133722 1.365985 0.151068 0.056 Uiso 1 1 calc R U . . .
H5AB H -0.088289 1.241137 0.082187 0.056 Uiso 1 1 calc R U . . .
C6 C -0.1560(10) 1.1302(7) 0.1993(5) 0.0446(15) Uani 1 1 d . . . . .
H6A H -0.235449 1.163139 0.251939 0.054 Uiso 1 1 calc R U . . .
H6AB H -0.203508 1.037794 0.183543 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0598(11) 1.0799(7) 0.2083(4) 0.0452(16) Uani 1 1 d . . . . .
H7A H 0.102495 1.172706 0.226284 0.054 Uiso 1 1 calc R U . . .
H7AB H 0.137812 1.056914 0.154044 0.054 Uiso 1 1 calc R U . . .
C8 C 0.1063(10) 0.9317(7) 0.2683(5) 0.0466(16) Uani 1 1 d . . . . .
H8A H 0.034101 0.955177 0.323432 0.056 Uiso 1 1 calc R U . . .
H8AB H 0.061666 0.838531 0.251711 0.056 Uiso 1 1 calc R U . . .
C9 C 0.3263(10) 0.8867(7) 0.2710(4) 0.0453(15) Uani 1 1 d . . . . .
H9A H 0.370147 0.981083 0.286768 0.054 Uiso 1 1 calc R U . . .
H9AB H 0.397354 0.863594 0.215674 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3821(10) 0.7394(7) 0.3307(4) 0.0453(15) Uani 1 1 d . . . . .
H10A H 0.318821 0.764362 0.386822 0.054 Uiso 1 1 calc R U . . .
H10B H 0.332991 0.645731 0.317166 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6037(10) 0.6949(7) 0.3268(4) 0.0446(15) Uani 1 1 d . . . . .
H11A H 0.649344 0.784744 0.346185 0.053 Uiso 1 1 calc R U . . .
H11B H 0.666972 0.683621 0.269393 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6707(11) 0.5363(8) 0.3781(5) 0.0502(17) Uani 1 1 d . . . . .
H12A H 0.614234 0.549420 0.436097 0.060 Uiso 1 1 calc R U . . .
H12B H 0.619657 0.447042 0.360896 0.060 Uiso 1 1 calc R U . . .
C13 C 0.8950(11) 0.4902(8) 0.3690(5) 0.0485(16) Uani 1 1 d . . . . .
H13A H 0.945757 0.580216 0.385555 0.058 Uiso 1 1 calc R U . . .
H13B H 0.950935 0.476351 0.311015 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9647(11) 0.3332(7) 0.4203(5) 0.0500(17) Uani 1 1 d . . . . .
H14A H 0.906739 0.345899 0.478247 0.060 Uiso 1 1 calc R U . . .
H14B H 0.916913 0.242451 0.402930 0.060 Uiso 1 1 calc R U . . .
C15 C 1.1874(12) 0.2912(8) 0.4122(5) 0.059(2) Uani 1 1 d . . . . .
H15A H 1.235139 0.383626 0.427893 0.071 Uiso 1 1 calc R U . . .
H15B H 1.244663 0.275695 0.354457 0.071 Uiso 1 1 calc R U . . .
C16 C 1.2596(16) 0.1388(10) 0.4644(6) 0.074(3) Uani 1 1 d . . . . .
H16A H 1.232587 0.043714 0.443357 0.112 Uiso 1 1 calc R U . . .
H16B H 1.192459 0.147462 0.520861 0.112 Uiso 1 1 calc R U . . .
H16C H 1.399647 0.128675 0.462198 0.112 Uiso 1 1 calc R U . . .
N2 N -0.3778(8) 1.3248(6) 0.1162(4) 0.0416(13) Uani 1 1 d . . . . .
Br01 Br 0.84530(10) 0.72017(7) 0.08930(4) 0.0438(3) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 N3 107.7(6) . . ?
N3 C2 N2 106.5(6) . . ?
N3 C2 C4 126.3(6) . . ?
N2 C2 C4 127.2(6) . . ?
C1 C3 N2 106.2(6) . . ?
C2 N3 C1 110.0(6) . . ?
N2 C5 C6 114.0(5) . . ?
C7 C6 C5 109.6(5) . . ?
C6 C7 C8 115.9(5) . . ?
C9 C8 C7 112.3(5) . . ?
C8 C9 C10 114.7(5) . . ?
C11 C10 C9 112.1(5) . . ?
C10 C11 C12 114.6(5) . . ?
C13 C12 C11 113.1(5) . . ?
C12 C13 C14 113.9(6) . . ?
C15 C14 C13 113.3(6) . . ?
C14 C15 C16 114.2(7) . . ?
C2 N2 C3 109.6(6) . . ?
C2 N2 C5 125.3(6) . . ?
C3 N2 C5 125.1(6) . . ?
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
C1 C3 1.347(10) . ?
C1 N3 1.383(10) . ?
C2 N3 1.331(8) . ?
C2 N2 1.360(9) . ?
C2 C4 1.472(10) . ?
C3 N2 1.391(9) . ?
C5 N2 1.465(9) . ?
C5 C6 1.527(8) . ?
C6 C7 1.519(10) . ?
C7 C8 1.520(8) . ?
C8 C9 1.520(10) . ?
C9 C10 1.525(8) . ?
C10 C11 1.513(10) . ?
C11 C12 1.533(8) . ?
C12 C13 1.523(10) . ?
C13 C14 1.529(9) . ?
C14 C15 1.511(11) . ?
C15 C16 1.514(10) . ?
