#------------------------------------------------------------------------------
#$Date: 2019-11-22 07:47:17 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231192 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/52/7235251.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_7235251
loop_
_publ_author_name
'Munir, Naima'
'Masood, Sara'
'Liaqat, Faroha'
'Tahir, Muhammad Nawaz'
'Yousuf, Sammer'
'Kalsoom, Saima'
'Mughal, Ehsan Ullah'
'Sumrra, Sajjad Hussain'
'Maalik, Aneela'
'Zafar, Muhammad Naveed'
_publ_section_title
;
 Synthesis of new Pro-PYE ligands as co-catalysts toward Pd-catalyzed
 Heck--Mizoroki cross coupling reactions
;
_journal_issue                   65
_journal_name_full               'RSC Advances'
_journal_page_first              37986
_journal_paper_doi               10.1039/C9RA07912B
_journal_volume                  9
_journal_year                    2019
_chemical_formula_iupac          'C16 H24 I2 N4'
_chemical_formula_moiety         'C16 H24 N4, 2(I)'
_chemical_formula_sum            'C16 H24 I2 N4'
_chemical_formula_weight         526.19
_chemical_melting_point          577.15
_chemical_name_systematic
;
2,2'-(Ethane-1,2-diylbis(azanediyl))bis(1-ethylpyridin-1-ium) chloride
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   25.3399(9)
_cell_length_b                   25.3399(9)
_cell_length_c                   8.0684(2)
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.000
_cell_measurement_theta_min      2.690
_cell_volume                     4486.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.83
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6081
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.690
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.157
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            'Fawn yellow solid'
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2286
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.078
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0373
_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)+(0.0396P)²+12.5789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1694
_reflns_number_total             2153
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c9ra07912b2.cif
_cod_data_source_block           dsaqaun
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '304 \oC' was changed to
'577.15' -- it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7235251
_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N1 N 0.11119(16) 0.26018(16) 0.2327(5) 0.0651(9) Uani 1 1 d . . . . .
H1 H 0.118300 0.230357 0.234422 0.078 Uiso 1 1 calc R U . . .
N2 N 0.00854(17) 0.18805(19) 0.2134(6) 0.0768(12) Uani 1 1 d . . . . .
C1 C 0.16313(19) 0.3223(2) 0.2454(5) 0.0608(10) Uani 1 1 d . . . . .
H1A H 0.156755 0.349151 0.173082 0.073 Uiso 1 1 calc R U . . .
H1B H 0.200005 0.322806 0.210252 0.073 Uiso 1 1 calc R U . . .
C2 C 0.05365(18) 0.24735(18) 0.2186(5) 0.0540(9) Uani 1 1 d . . . . .
C3 C 0.03666(19) 0.2917(2) 0.2055(5) 0.0583(10) Uani 1 1 d . . . . .
H3 H 0.066345 0.332573 0.213135 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0223(2) 0.2763(2) 0.1819(6) 0.0675(12) Uani 1 1 d . . . . .
H4 H -0.032816 0.306445 0.171033 0.081 Uiso 1 1 calc R U . . .
C5 C -0.0665(2) 0.2158(3) 0.1741(6) 0.0762(14) Uani 1 1 d . . . . .
H5 H -0.107136 0.204550 0.157851 0.091 Uiso 1 1 calc R U . . .
C6 C -0.0504(2) 0.1739(3) 0.1901(7) 0.0858(16) Uani 1 1 d . . . . .
H6 H -0.080489 0.133093 0.185398 0.103 Uiso 1 1 calc R U . . .
C7A C 0.0269(8) 0.1418(7) 0.180(2) 0.112(2) Uani 0.533(8) 1 d D . P A 1
H7A H 0.010874 0.122585 0.073184 0.135 Uiso 0.533(8) 1 calc R U P A 1
H7B H 0.071003 0.161273 0.175573 0.135 Uiso 0.533(8) 1 calc R U P A 1
C8A C 0.0033(7) 0.0958(6) 0.3107(17) 0.112(2) Uani 0.533(8) 1 d D . P A 1
H8A H 0.032460 0.108309 0.399062 0.168 Uiso 0.533(8) 1 calc R U P A 1
H8B H -0.003909 0.057539 0.266801 0.168 Uiso 0.533(8) 1 calc R U P A 1
H8C H -0.034233 0.091352 0.352186 0.168 Uiso 0.533(8) 1 calc R U P A 1
C7B C 0.0216(10) 0.1382(8) 0.289(2) 0.112(2) Uani 0.467(8) 1 d D . P A 2
H7C H 0.060187 0.156782 0.347866 0.135 Uiso 0.467(8) 1 calc R U P A 2
H7D H -0.010699 0.111223 0.363974 0.135 Uiso 0.467(8) 1 calc R U P A 2
C8B C 0.0234(8) 0.1056(7) 0.1392(19) 0.112(2) Uani 0.467(8) 1 d D . P A 2
H8D H 0.047436 0.134679 0.055409 0.168 Uiso 0.467(8) 1 calc R U P A 2
H8E H -0.017335 0.080112 0.098580 0.168 Uiso 0.467(8) 1 calc R U P A 2
H8F H 0.041095 0.080950 0.166052 0.168 Uiso 0.467(8) 1 calc R U P A 2
I1 I 0.20299(2) 0.19160(2) 0.29278(4) 0.07055(16) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C1 123.7(4) . .
C2 N1 H1 118.2 . .
C1 N1 H1 118.2 . .
C2 N2 C6 120.0(4) . .
C2 N2 C7A 117.1(7) . .
C6 N2 C7A 120.1(8) . .
C2 N2 C7B 118.3(8) . .
C6 N2 C7B 118.9(8) . .
N1 C1 C1 110.0(5) . 16
N1 C1 H1A 109.7 . .
C1 C1 H1A 109.7 16 .
N1 C1 H1B 109.7 . .
C1 C1 H1B 109.7 16 .
H1A C1 H1B 108.2 . .
N1 C2 N2 119.1(4) . .
N1 C2 C3 123.5(4) . .
N2 C2 C3 117.4(4) . .
C4 C3 C2 121.3(4) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C4 C5 119.5(5) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 119.0(5) . .
C6 C5 H5 120.5 . .
C4 C5 H5 120.5 . .
C5 C6 N2 122.8(5) . .
C5 C6 H6 118.6 . .
N2 C6 H6 118.6 . .
C8A C7A N2 109.3(12) . .
C8A C7A H7A 109.8 . .
N2 C7A H7A 109.8 . .
C8A C7A H7B 109.8 . .
N2 C7A H7B 109.8 . .
H7A C7A H7B 108.3 . .
C7A C8A H8A 109.5 . .
C7A C8A H8B 109.5 . .
H8A C8A H8B 109.5 . .
C7A C8A H8C 109.5 . .
H8A C8A H8C 109.5 . .
H8B C8A H8C 109.5 . .
C8B C7B N2 101.8(13) . .
C8B C7B H7C 111.4 . .
N2 C7B H7C 111.4 . .
C8B C7B H7D 111.4 . .
N2 C7B H7D 111.4 . .
H7C C7B H7D 109.3 . .
C7B C8B H8D 109.5 . .
C7B C8B H8E 109.5 . .
H8D C8B H8E 109.5 . .
C7B C8B H8F 109.5 . .
H8D C8B H8F 109.5 . .
H8E C8B H8F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.331(5) .
N1 C1 1.465(6) .
N1 H1 0.8600 .
N2 C2 1.360(5) .
N2 C6 1.363(6) .
N2 C7A 1.488(15) .
N2 C7B 1.580(17) .
C1 C1 1.503(9) 16
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.393(6) .
C3 C4 1.357(6) .
C3 H3 0.9300 .
C4 C5 1.375(7) .
C4 H4 0.9300 .
C5 C6 1.320(8) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7A C8A 1.462(14) .
C7A H7A 0.9700 .
C7A H7B 0.9700 .
C8A H8A 0.9600 .
C8A H8B 0.9600 .
C8A H8C 0.9600 .
C7B C8B 1.479(15) .
C7B H7C 0.9700 .
C7B H7D 0.9700 .
C8B H8D 0.9600 .
C8B H8E 0.9600 .
C8B H8F 0.9600 .
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
_geom_hbond_publ_flag
N1 H1 I1 0.86 2.81 3.565(4) 147.3 . yes
C6 H6 I1 0.93 3.08 3.964(5) 158.8 2 yes
C7A^a H7B^a I1 0.97 3.18 4.087(18) 156.6 . yes
C7B^b H7C^b I1 0.97 3.30 4.09(2) 140.3 . yes
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
_geom_torsion_site_symmetry_4
C2 N1 C1 C1 82.2(6) 16
C1 N1 C2 N2 -177.7(4) .
C1 N1 C2 C3 3.5(7) .
C6 N2 C2 N1 -176.5(5) .
C7A N2 C2 N1 -15.6(9) .
C7B N2 C2 N1 22.6(9) .
C6 N2 C2 C3 2.3(7) .
C7A N2 C2 C3 163.2(8) .
C7B N2 C2 C3 -158.6(8) .
N1 C2 C3 C4 176.2(4) .
N2 C2 C3 C4 -2.6(7) .
C2 C3 C4 C5 1.4(7) .
C3 C4 C5 C6 0.1(7) .
C4 C5 C6 N2 -0.3(9) .
C2 N2 C6 C5 -0.9(9) .
C7A N2 C6 C5 -161.3(8) .
C7B N2 C6 C5 159.9(8) .
C2 N2 C7A C8A 125.8(11) .
C6 N2 C7A C8A -73.3(15) .
C2 N2 C7B C8B -110.5(12) .
C6 N2 C7B C8B 88.4(13) .
