 
data_pjr14ajcs011
 
_audit_creation_method            'SHELXL-2016/4'
_shelx_SHELXL_version_number      '2016/4'
_chemical_name_systematic         '1,4,8,11-tetra(prop-2-yn-1-yl)-1,4,8,11-tetraazacyclotetradecane-1,8-diium perchlorate'
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H34 N4, 2(Cl O4)'
_chemical_formula_sum
 'C22 H34 Cl2 N4 O8' 
_chemical_formula_weight          553.43

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.3639   0.7018
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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'
 
_cell_length_a                    9.7218(3)
_cell_length_b                    14.1376(2)
_cell_length_c                    10.2523(2)
_cell_angle_alpha                 90
_cell_angle_beta                  115.650(3)
_cell_angle_gamma                 90
_cell_volume                      1270.25(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     16838
_cell_measurement_theta_min       5.2110
_cell_measurement_theta_max       75.4330
 
_exptl_crystal_description        'prism'
_exptl_crystal_colour             'clear light colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.447          
_exptl_crystal_F_000              584
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.05
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.01
_exptl_absorpt_coefficient_mu     2.772
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.82343
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_ambient_environment 'N~2~'
_diffrn_source 'sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method 'ω scans'
_diffrn_detector 'CCD plate'
_diffrn_detector_type 'Atlas'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number             37188
_diffrn_reflns_av_unetI/netI      0.0241
_diffrn_reflns_av_R_equivalents   0.0598
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          3.1259
_diffrn_reflns_theta_max          76.1941
_diffrn_reflns_theta_full         74.3338
_diffrn_measured_fraction_theta_max   0.9953
_diffrn_measured_fraction_theta_full  0.9989
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              2646
_reflns_number_gt                 2352
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34i (release 04-08-2014 CrysAlis171 .NET)
(compiled Aug  4 2014,14:34:23)
;
_computing_structure_solution     'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0474P)²+0.5288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2646
_refine_ls_number_parameters      168
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0410
_refine_ls_R_factor_gt            0.0343
_refine_ls_wR_factor_ref          0.0909
_refine_ls_wR_factor_gt           0.0869
_refine_ls_goodness_of_fit_ref    1.058
_refine_ls_restrained_S_all       1.058
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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 0.17310(18) 0.00178(10) -0.14639(16) 0.0236(3) Uani 1 1 d . . . . .
H1A H 0.205628 0.064472 -0.106509 0.028 Uiso 1 1 calc R U . . .
H1B H 0.067941 -0.006598 -0.162382 0.028 Uiso 1 1 calc R U . . .
C2 C 0.18363(17) -0.00677(11) -0.28939(16) 0.0245(3) Uani 1 1 d . . . . .
H2B H 0.134991 -0.065039 -0.337038 0.029 Uiso 1 1 calc R U . . .
H2A H 0.129615 0.045560 -0.351724 0.029 Uiso 1 1 calc R U . . .
C3 C 0.41900(18) 0.09054(10) -0.22019(16) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.427897 0.103175 -0.123861 0.032(5) Uiso 1 1 calc R . . . .
H3B H 0.350353 0.137438 -0.284776 0.039 Uiso 1 1 calc R U . . .
C4 C 0.57510(19) 0.10307(11) -0.21832(17) 0.0263(3) Uani 1 1 d . . . . .
H4A H 0.602489 0.169452 -0.202268 0.032 Uiso 1 1 calc R U . . .
H4B H 0.567235 0.086581 -0.313139 0.032 Uiso 1 1 calc R U . . .
C5 C 0.70419(17) 0.04530(10) -0.10539(16) 0.0233(3) Uani 1 1 d . . . . .
H5B H 0.679560 -0.021425 -0.122044 0.028 Uiso 1 1 calc R U . . .
H5A H 0.797118 0.056295 -0.116356 0.028 Uiso 1 1 calc R U . . .
C6 C 0.79496(19) 0.16552(10) 0.08315(17) 0.0250(3) Uani 1 1 d . . . . .
H6A H 0.718488 0.211027 0.024549 0.030 Uiso 1 1 calc R U . . .
H6B H 0.816537 0.176966 0.183450 0.030 Uiso 1 1 calc R U . . .
C7 C 0.93502(19) 0.18216(11) 0.06515(17) 0.0266(3) Uani 1 1 d . . . . .
C8 C 1.0453(2) 0.19548(13) 0.0449(2) 0.0350(4) Uani 1 1 d . . . . .
H8 H 1.131297 0.205882 0.029073 0.042 Uiso 1 1 calc R U . . .
C9 C 0.35901(19) -0.04343(11) -0.40007(16) 0.0260(3) Uani 1 1 d . . . . .
H9A H 0.465158 -0.054875 -0.378185 0.031 Uiso 1 1 calc R U . . .
H9B H 0.304715 -0.103040 -0.428731 0.031 Uiso 1 1 calc R U . . .
C10 C 0.29404(19) 0.02426(12) -0.51932(17) 0.0288(3) Uani 1 1 d . . . . .
C11 C 0.2434(2) 0.08066(14) -0.61288(18) 0.0380(4) Uani 1 1 d . . . . .
H11 H 0.203488 0.125160 -0.686706 0.046 Uiso 1 1 calc R U . . .
N1 N 0.73074(14) 0.06951(8) 0.04316(13) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.34803(15) -0.00638(9) -0.26709(13) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.43489(15) 0.16464(8) 0.11193(14) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.48879(16) 0.30113(10) 0.01219(14) 0.0399(3) Uani 1 1 d . . . . .
O3 O 0.36621(16) 0.31449(10) 0.16400(16) 0.0429(3) Uani 1 1 d . . . . .
O4 O 0.62463(14) 0.26899(9) 0.26144(14) 0.0341(3) Uani 1 1 d . . . . .
CL1 Cl 0.47841(4) 0.26313(2) 0.13812(4) 0.02378(12) Uani 1 1 d . . . . .
HN2 H 0.396(2) -0.0468(14) -0.199(2) 0.026(5) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 N1 1.4674(18) 3_655 ?
C1 C2 1.518(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N2 1.5133(19) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C3 N2 1.5157(18) . ?
C3 C4 1.520(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.525(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.4707(18) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C7 1.470(2) . ?
C6 N1 1.4760(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.192(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.463(2) . ?
C9 N2 1.5069(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.179(3) . ?
C11 H11 0.9300 . ?
N1 C1 1.4675(18) 3_655 ?
N2 HN2 0.87(2) . ?
O1 CL1 1.4462(11) . ?
O2 CL1 1.4418(13) . ?
O3 CL1 1.4276(13) . ?
O4 CL1 1.4388(13) . ?
 
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
N1 C1 C2 110.71(12) 3_655 . ?
N1 C1 H1A 109.5 3_655 . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 3_655 . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 111.23(12) . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
H2B C2 H2A 108.0 . . ?
N2 C3 C4 115.11(12) . . ?
N2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 C5 115.88(12) . . ?
C3 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C3 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
N1 C5 C4 112.30(12) . . ?
N1 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
N1 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
H5B C5 H5A 107.9 . . ?
C7 C6 N1 114.57(12) . . ?
C7 C6 H6A 108.6 . . ?
N1 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
N1 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 177.45(17) . . ?
C7 C8 H8 180.0 . . ?
C10 C9 N2 110.77(12) . . ?
C10 C9 H9A 109.5 . . ?
N2 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 178.27(19) . . ?
C10 C11 H11 180.0 . . ?
C1 N1 C5 111.00(11) 3_655 . ?
C1 N1 C6 111.74(12) 3_655 . ?
C5 N1 C6 111.42(11) . . ?
C9 N2 C2 110.23(12) . . ?
C9 N2 C3 113.60(11) . . ?
C2 N2 C3 110.93(11) . . ?
C9 N2 HN2 106.1(13) . . ?
C2 N2 HN2 106.5(13) . . ?
C3 N2 HN2 109.1(13) . . ?
O3 CL1 O4 110.56(8) . . ?
O3 CL1 O2 109.40(9) . . ?
O4 CL1 O2 109.87(8) . . ?
O3 CL1 O1 109.79(8) . . ?
O4 CL1 O1 108.48(8) . . ?
O2 CL1 O1 108.71(8) . . ?
 
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_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
N1 C1 C2 N2 -52.07(16) 3_655 . . . ?
N2 C3 C4 C5 -67.14(17) . . . . ?
C3 C4 C5 N1 -61.39(17) . . . . ?
C4 C5 N1 C1 165.87(12) . . . 3_655 ?
C4 C5 N1 C6 -68.90(15) . . . . ?
C7 C6 N1 C1 69.99(16) . . . 3_655 ?
C7 C6 N1 C5 -54.83(17) . . . . ?
C10 C9 N2 C2 70.54(16) . . . . ?
C10 C9 N2 C3 -54.66(17) . . . . ?
C1 C2 N2 C9 163.15(12) . . . . ?
C1 C2 N2 C3 -70.13(15) . . . . ?
C4 C3 N2 C9 -45.71(17) . . . . ?
C4 C3 N2 C2 -170.54(12) . . . . ?
 
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 
C3 H3A O1  0.97 2.54 3.5014(19) 170.1 .
C6 H6A O2  0.97 2.53 3.345(2) 142.1 .
N2 HN2 O1_$1  0.87(2) 2.24(2) 3.0139(18) 149.2(17) 3_655
 
_refine_diff_density_max    0.260
_refine_diff_density_min   -0.483
_refine_diff_density_rms    0.050



