#------------------------------------------------------------------------------
#$Date: 2023-06-05 08:03:32 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/90/1569071.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_1569071
loop_
_publ_author_name
'Mahapatra, Amita'
'Samantara, Aneeya K.'
'Barik, Sahadev'
'Sahoo, Malaya K.'
'Behera, J. N.'
'Sarkar, Moloy'
_publ_section_title
;
 Insight into the structure and transport properties of
 pyrrolidinium-based geminal dicationic-organic ionic crystals:
 unravelling the role of alkyl-chain length.
;
_journal_issue                   19
_journal_name_full               'Soft matter'
_journal_page_first              3510
_journal_page_last               3518
_journal_paper_doi               10.1039/d3sm00040k
_journal_volume                  19
_journal_year                    2023
_chemical_formula_moiety         'Br, C9 H19 N, H2 O'
_chemical_formula_sum            'C9 H21 Br N O'
_chemical_formula_weight         239.18
_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     direct
_audit_creation_date             2022-11-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                94.525(5)
_cell_angle_beta                 105.831(5)
_cell_angle_gamma                117.457(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7747(6)
_cell_length_b                   8.8458(6)
_cell_length_c                   8.9862(5)
_cell_measurement_reflns_used    7724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2670
_cell_measurement_theta_min      3.8170
_cell_volume                     578.09(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  53.00   0.50    7.50    --    3.67-122.00 -58.00  106
  2  ω     16.00  72.00   0.50    7.50    --    3.67-151.00 139.00  112
  3  ω     16.00  64.00   0.50    7.50    --   -3.98-151.00 139.00   96
  4  ω    -20.00  40.00   0.50    7.50    --    3.67 -99.00-180.00  120
  5  ω    -59.00  15.00   0.50    7.50    --    3.67 -57.00  30.00  148
  6  ω    -19.00  68.00   0.50    7.50    --    3.67  77.00-180.00  174
  7  ω    -66.00   9.00   0.50    7.50    --    3.67 -19.00  60.00  150
  8  ω    -66.00   9.00   0.50    7.50    --    3.67 -19.00 150.00  150
  9  ω      0.00  70.00   0.50    7.50    --    3.67  38.00 120.00  140
 10  ω    -57.00 -26.00   0.50    7.50    --   -3.98 128.00 171.81   62
 11  ω    -10.00  66.00   0.50    7.50    --   -3.98  19.00   0.00  152
 12  ω    -56.00 -24.00   0.50    7.50    --   -3.98 126.00  74.31   64
 13  ω    -68.00  19.00   0.50    7.50    --   -3.98 -77.00   0.00  174
 14  ω    -56.00 -24.00   0.50    7.50    --   -3.98 126.00 -11.41   64
 15  ω    -55.00 -23.00   0.50    7.50    --   -3.98 125.00 135.60   64
 16  ω    -67.00   8.00   0.50    7.50    --   -3.98 -57.00-120.00  150
 17  ω    -59.00 -27.00   0.50    7.50    --   -3.98 131.00-158.65   64
 18  ω    -62.00 -31.00   0.50    7.50    --   -3.98 137.00-109.45   62
 19  ω    -59.00 -27.00   0.50    7.50    --   -3.98 131.00 -47.23   64
 20  ω     -2.00  52.00   0.50    7.50    --    3.67-120.00  14.51  108
 21  ω    -20.00  40.00   0.50    7.50    --    3.67 -99.00-150.00  120
 22  ω     -2.00  52.00   0.50    7.50    --    3.67-120.00-172.17  108
 23  ω    -71.00 -36.00   0.50    7.50    --   -3.98 150.00-148.35   70
 24  ω    -70.00  -1.00   0.50    7.50    --   -3.98 -38.00  90.00  138
 25  ω    -20.00  32.00   0.50    7.50    --   -3.98 -99.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0117967000
_diffrn_orient_matrix_UB_12      0.0017723000
_diffrn_orient_matrix_UB_13      0.0815319000
_diffrn_orient_matrix_UB_21      -0.0951406000
_diffrn_orient_matrix_UB_22      -0.0597830000
_diffrn_orient_matrix_UB_23      -0.0212124000
_diffrn_orient_matrix_UB_31      0.0161965000
_diffrn_orient_matrix_UB_32      -0.0713187000
_diffrn_orient_matrix_UB_33      -0.0066343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22871
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.723
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       plate
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0525
_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)+(0.0930P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1736
_reflns_number_total             2438
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sm00040k2.cif
_cod_data_source_block           ms_29072019
_cod_depositor_comments
'Adding full bibliography for 1569069--1569071.cif.'
_cod_original_cell_volume        578.09(7)
_cod_database_code               1569071
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C16 H34 Br2 N4 O2 '
_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.
;
_diffrn_oxdiff_ac3_digest_frames
;
01a353dd1e6b445ba9390ae3b322e76ea7000264de2
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e48a57c1f8a251daf7ae1b4e62572dafc34b
;
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C004(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F), C007(H00G,H00H), C009(H00L,
 H00M), C00A(H00N,H00O), C00B(H00P,H00Q), C00C(H00R,H00S)
2.b Idealised Me refined as rotating group:
 C008(H00I,H00J,H00K)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.096
_oxdiff_exptl_absorpt_empirical_full_min 0.470
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
Br01 Br 0.68229(5) 0.83841(5) 0.26108(5) 0.0735(2) Uani 1 1 d . . . . .
N002 N 0.5018(4) 0.2315(4) 0.3247(4) 0.0537(7) Uani 1 1 d . . . . .
O003 O 0.9610(7) 0.7565(6) 0.5341(7) 0.1209(16) Uani 1 1 d . . . . .
C004 C 0.4114(6) 0.3390(5) 0.3020(6) 0.0653(10) Uani 1 1 d . . . . .
H00A H 0.392484 0.370206 0.398688 0.078 Uiso 1 1 calc R . . . .
H00B H 0.485641 0.445850 0.273917 0.078 Uiso 1 1 calc R . . . .
C005 C 0.7408(6) 0.3897(5) 0.2029(6) 0.0679(10) Uani 1 1 d . . . . .
H00C H 0.837686 0.430347 0.305578 0.081 Uiso 1 1 calc R . . . .
H00D H 0.706898 0.478981 0.188708 0.081 Uiso 1 1 calc R . . . .
C006 C 0.5793(5) 0.2223(5) 0.1970(5) 0.0591(9) Uani 1 1 d . . . . .
H00E H 0.614283 0.133215 0.204846 0.071 Uiso 1 1 calc R . . . .
H00F H 0.483693 0.185074 0.094086 0.071 Uiso 1 1 calc R . . . .
C007 C 0.3430(7) 0.0548(5) 0.3047(7) 0.0765(13) Uani 1 1 d . . . . .
H00G H 0.369055 -0.036607 0.276248 0.092 Uiso 1 1 calc R . . . .
H00H H 0.316693 0.045026 0.402692 0.092 Uiso 1 1 calc R . . . .
C008 C 0.6452(7) 0.2962(7) 0.4853(6) 0.0774(12) Uani 1 1 d . . . . .
H00I H 0.737007 0.415460 0.497906 0.116 Uiso 1 1 calc GR . . . .
H00J H 0.700788 0.224353 0.496414 0.116 Uiso 1 1 calc GR . . . .
H00K H 0.590519 0.290769 0.565262 0.116 Uiso 1 1 calc GR . . . .
C009 C 0.8067(6) 0.3581(6) 0.0725(6) 0.0711(11) Uani 1 1 d . . . . .
H00L H 0.834394 0.264647 0.085633 0.085 Uiso 1 1 calc R . . . .
H00M H 0.708625 0.318627 -0.029215 0.085 Uiso 1 1 calc R . . . .
C00A C 0.9710(6) 0.5146(6) 0.0689(6) 0.0742(11) Uani 1 1 d . . . . .
H00N H 1.071637 0.549219 0.167641 0.089 Uiso 1 1 calc R . . . .
H00O H 0.946230 0.610469 0.062997 0.089 Uiso 1 1 calc R . . . .
C00B C 0.2338(7) 0.2273(7) 0.1709(8) 0.0856(14) Uani 1 1 d . . . . .
H00P H 0.244653 0.249878 0.069339 0.103 Uiso 1 1 calc R . . . .
H00Q H 0.140356 0.249372 0.187312 0.103 Uiso 1 1 calc R . . . .
C00C C 0.1858(7) 0.0389(6) 0.1752(8) 0.0891(16) Uani 1 1 d . . . . .
H00R H 0.073400 -0.022296 0.197713 0.107 Uiso 1 1 calc R . . . .
H00S H 0.170608 -0.024488 0.074176 0.107 Uiso 1 1 calc R . . . .
H00T H 1.017(5) 0.788(5) 0.464(4) 0.028(8) Uiso 1 1 d . . . . .
H00U H 1.058(9) 0.865(9) 0.553(9) 0.12(2) Uiso 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'
Br Br -0.2901 2.4595 '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'
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
C004 N002 C006 112.0(3) . . ?
C004 N002 C007 101.3(3) . . ?
C007 N002 C006 108.8(3) . . ?
C008 N002 C004 111.4(3) . . ?
C008 N002 C006 110.8(3) . . ?
C008 N002 C007 112.2(4) . . ?
H00T O003 H00U 58(4) . . ?
N002 C004 H00A 110.6 . . ?
N002 C004 H00B 110.6 . . ?
H00A C004 H00B 108.8 . . ?
C00B C004 N002 105.5(3) . . ?
C00B C004 H00A 110.6 . . ?
C00B C004 H00B 110.6 . . ?
H00C C005 H00D 108.3 . . ?
C006 C005 H00C 110.0 . . ?
C006 C005 H00D 110.0 . . ?
C006 C005 C009 108.6(3) . . ?
C009 C005 H00C 110.0 . . ?
C009 C005 H00D 110.0 . . ?
N002 C006 H00E 108.5 . . ?
N002 C006 H00F 108.5 . . ?
C005 C006 N002 114.9(3) . . ?
C005 C006 H00E 108.5 . . ?
C005 C006 H00F 108.5 . . ?
H00E C006 H00F 107.5 . . ?
N002 C007 H00G 110.5 . . ?
N002 C007 H00H 110.5 . . ?
H00G C007 H00H 108.7 . . ?
C00C C007 N002 106.0(4) . . ?
C00C C007 H00G 110.5 . . ?
C00C C007 H00H 110.5 . . ?
N002 C008 H00I 109.5 . . ?
N002 C008 H00J 109.5 . . ?
N002 C008 H00K 109.5 . . ?
H00I C008 H00J 109.5 . . ?
H00I C008 H00K 109.5 . . ?
H00J C008 H00K 109.5 . . ?
C005 C009 H00L 108.8 . . ?
C005 C009 H00M 108.8 . . ?
H00L C009 H00M 107.7 . . ?
C00A C009 C005 113.8(4) . . ?
C00A C009 H00L 108.8 . . ?
C00A C009 H00M 108.8 . . ?
C009 C00A C00A 113.5(5) . 2_765 ?
C009 C00A H00N 108.9 . . ?
C009 C00A H00O 108.9 . . ?
C00A C00A H00N 108.9 2_765 . ?
C00A C00A H00O 108.9 2_765 . ?
H00N C00A H00O 107.7 . . ?
C004 C00B H00P 110.7 . . ?
C004 C00B H00Q 110.7 . . ?
C004 C00B C00C 105.4(4) . . ?
H00P C00B H00Q 108.8 . . ?
C00C C00B H00P 110.7 . . ?
C00C C00B H00Q 110.7 . . ?
C007 C00C C00B 105.1(4) . . ?
C007 C00C H00R 110.7 . . ?
C007 C00C H00S 110.7 . . ?
C00B C00C H00R 110.7 . . ?
C00B C00C H00S 110.7 . . ?
H00R C00C H00S 108.8 . . ?
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
N002 C004 1.488(5) . ?
N002 C006 1.499(5) . ?
N002 C007 1.492(5) . ?
N002 C008 1.486(6) . ?
O003 H00T 0.89(3) . ?
O003 H00U 0.90(7) . ?
C004 H00A 0.9700 . ?
C004 H00B 0.9700 . ?
C004 C00B 1.479(7) . ?
C005 H00C 0.9700 . ?
C005 H00D 0.9700 . ?
C005 C006 1.488(6) . ?
C005 C009 1.501(6) . ?
C006 H00E 0.9700 . ?
C006 H00F 0.9700 . ?
C007 H00G 0.9700 . ?
C007 H00H 0.9700 . ?
C007 C00C 1.482(8) . ?
C008 H00I 0.9600 . ?
C008 H00J 0.9600 . ?
C008 H00K 0.9600 . ?
C009 H00L 0.9700 . ?
C009 H00M 0.9700 . ?
C009 C00A 1.479(6) . ?
C00A C00A 1.507(9) 2_765 ?
C00A H00N 0.9700 . ?
C00A H00O 0.9700 . ?
C00B H00P 0.9700 . ?
C00B H00Q 0.9700 . ?
C00B C00C 1.526(7) . ?
C00C H00R 0.9700 . ?
C00C H00S 0.9700 . ?
