#------------------------------------------------------------------------------
#$Date: 2023-07-05 05:16:25 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022810.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_2022810
loop_
_publ_author_name
'Mammadova, Gunay Z.'
'Mertsalov, Dmitriy F.'
'Shchevnikov, Dmitriy M.'
'Grigoriev, Mikhail S.'
'Akkurt, Mehmet'
'Yıldırım, Sema Öztürk'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of
 N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol tribromide
 (1/1), N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol
 dibromidoiodate (1/1) and
 N,N-dimethylacetamide--1-(dimethyl-λ4-azanylidene)ethan-1-ol
 dichloridoiodate (1/1)
;
_journal_coeditor_code           YZ2034
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023005509
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C4 H9 N1 O1, C4 H10 N1 O1 -, Br2 I -'
_chemical_formula_moiety         'C4 H9 N1 O1, C4 H10 N1 O1 -, Br2 I -'
_chemical_formula_sum            'C8 H19 Br2 I N2 O2'
_chemical_formula_weight         461.97
_chemical_name_systematic
'N,N-Dimethylacetamide--1-(dimethyl-λ⁴-azanylidene)ethan-1-ol dibromidoiodate (1/1)'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90.645(2)
_cell_angle_beta                 103.651(2)
_cell_angle_gamma                93.656(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2943(3)
_cell_length_b                   7.9544(4)
_cell_length_c                   13.6097(7)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.15
_cell_measurement_theta_min      2.88
_cell_volume                     765.51(6)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30601
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.180
_diffrn_reflns_theta_min         4.261
_exptl_absorpt_coefficient_mu    7.299
_exptl_absorpt_correction_T_max  0.669
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_description       fragment
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.623
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         6766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0190
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0119P)²+0.2374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0376
_reflns_number_gt                5446
_reflns_number_total             6766
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2034sup1.cif
_cod_data_source_block           II
_cod_database_code               2022810
_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   0.428
_shelx_estimated_absorpt_t_max   0.669
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
I I1 0.65027(2) 0.18015(2) 0.21358(2) 0.01710(2) Uani d 1 . .
Br Br1 0.80118(2) 0.33097(2) 0.06912(2) 0.02346(3) Uani d 1 . .
Br Br2 0.51412(2) 0.02963(2) 0.35979(2) 0.02157(3) Uani d 1 . .
O O1 0.20994(14) 0.43799(12) 0.57436(7) 0.01964(19) Uani d 1 . .
H H1 0.187(6) 0.388(6) 0.617(3) 0.029 Uiso d 0.49(4) A 1
O O2 0.10583(13) 0.27819(13) 0.70454(7) 0.02121(19) Uani d 1 . .
H H2 0.151(5) 0.325(6) 0.659(3) 0.032 Uiso d 0.51(4) A 2
N N1 0.22672(15) 0.45877(13) 0.41323(8) 0.01563(19) Uani d 1 . .
N N2 0.14789(15) 0.19762(14) 0.86403(8) 0.0168(2) Uani d 1 . .
C C1 0.17805(16) 0.37110(15) 0.48569(9) 0.0147(2) Uani d 1 . .
C C2 0.08734(19) 0.19621(16) 0.46499(10) 0.0204(2) Uani d 1 . .
H H2A 0.080500 0.143984 0.529020 0.031 Uiso calc 1 . .
H H2B 0.162652 0.129403 0.430349 0.031 Uiso calc 1 . .
H H2C -0.040553 0.200696 0.422060 0.031 Uiso calc 1 . .
C C3 0.31786(18) 0.62905(16) 0.43360(10) 0.0198(2) Uani d 1 . .
H H3A 0.354648 0.651700 0.506798 0.030 Uiso calc 1 . .
H H3B 0.229380 0.711180 0.401612 0.030 Uiso calc 1 . .
H H3C 0.430563 0.638270 0.406042 0.030 Uiso calc 1 . .
C C4 0.1909(2) 0.39725(18) 0.30812(10) 0.0215(3) Uani d 1 . .
H H4A 0.104320 0.295852 0.298507 0.032 Uiso calc 1 . .
H H4B 0.310488 0.370162 0.292695 0.032 Uiso calc 1 . .
H H4C 0.134030 0.484580 0.262824 0.032 Uiso calc 1 . .
C C5 0.21588(17) 0.26890(15) 0.79243(9) 0.0155(2) Uani d 1 . .
C C6 0.41829(18) 0.33486(16) 0.81159(10) 0.0192(2) Uani d 1 . .
H H6A 0.438604 0.396328 0.752644 0.029 Uiso calc 1 . .
H H6B 0.500151 0.240498 0.823484 0.029 Uiso calc 1 . .
H H6C 0.448650 0.410935 0.871198 0.029 Uiso calc 1 . .
C C7 -0.0468(2) 0.12246(19) 0.84285(11) 0.0243(3) Uani d 1 . .
H H7A -0.107738 0.135459 0.771288 0.036 Uiso calc 1 . .
H H7B -0.117410 0.179306 0.884927 0.036 Uiso calc 1 . .
H H7C -0.045456 0.002396 0.858179 0.036 Uiso calc 1 . .
C C8 0.2581(2) 0.18213(19) 0.96814(10) 0.0236(3) Uani d 1 . .
H H8A 0.382190 0.242901 0.976432 0.035 Uiso calc 1 . .
H H8B 0.274782 0.062886 0.982492 0.035 Uiso calc 1 . .
H H8C 0.191026 0.230260 1.015097 0.035 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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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
Br2 I1 Br1 . . 177.942(6) ?
C1 O1 H1 . . 120(3) ?
C5 O2 H2 . . 118(3) ?
C1 N1 C3 . . 120.94(11) ?
C1 N1 C4 . . 123.49(11) ?
C3 N1 C4 . . 115.55(10) ?
C5 N2 C8 . . 123.75(11) ?
C5 N2 C7 . . 120.94(11) ?
C8 N2 C7 . . 115.28(11) ?
O1 C1 N1 . . 118.77(11) ?
O1 C1 C2 . . 120.38(11) ?
N1 C1 C2 . . 120.84(11) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O2 C5 N2 . . 118.46(12) ?
O2 C5 C6 . . 120.28(11) ?
N2 C5 C6 . . 121.25(11) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 H8A . . 109.5 ?
N2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
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
I1 Br2 . 2.68598(19) ?
I1 Br1 . 2.7243(2) ?
O1 C1 . 1.2771(15) ?
O1 H1 . 0.75(5) ?
O2 C5 . 1.2794(15) ?
O2 H2 . 0.85(5) ?
N1 C1 . 1.3168(16) ?
N1 C3 . 1.4640(16) ?
N1 C4 . 1.4648(17) ?
N2 C5 . 1.3121(16) ?
N2 C8 . 1.4656(17) ?
N2 C7 . 1.4673(17) ?
C1 C2 . 1.4961(17) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 C6 . 1.4965(18) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 . 0.75(5) 1.69(5) 2.4278(13) 173(4) yes
O2 H2 O1 . 0.85(5) 1.59(5) 2.4278(14) 170(4) yes
C2 H2A O2 . 0.98 2.57 3.2872(17) 130.3 yes
C2 H2B Br2 . 0.98 3.09 4.0105(14) 157.6 yes
C2 H2C I1 1_455 0.98 3.18 4.0838(14) 154.8 yes
C3 H3A Br2 2_666 0.98 3.07 3.8153(14) 134.2 yes
C3 H3B O2 2_566 0.98 2.54 3.3481(16) 140.1 yes
C4 H4A I1 1_455 0.98 3.31 4.1081(14) 140.3 yes
C6 H6A O1 . 0.98 2.64 3.3630(16) 131.0 yes
C6 H6C Br1 2_666 0.98 3.06 3.7331(14) 127.5 yes
C7 H7B Br1 1_456 0.98 2.97 3.8980(15) 158.5 yes
C8 H8A Br1 1_556 0.98 3.05 3.9722(15) 157.1 yes
C3 H3A O1 . 0.98 2.26 2.6878(16) 105 no
C7 H7A O2 . 0.98 2.24 2.6801(18) 106 no
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
C3 N1 C1 O1 . . . . 0.75(17) ?
C4 N1 C1 O1 . . . . -177.75(11) ?
C3 N1 C1 C2 . . . . -179.15(11) ?
C4 N1 C1 C2 . . . . 2.35(18) ?
C8 N2 C5 O2 . . . . -178.76(12) ?
C7 N2 C5 O2 . . . . 3.09(18) ?
C8 N2 C5 C6 . . . . 2.56(19) ?
C7 N2 C5 C6 . . . . -175.59(12) ?

_cod_database_fobs_code 2022810
