#------------------------------------------------------------------------------
#$Date: 2017-09-18 11:27:19 +0300 (Mon, 18 Sep 2017) $
#$Revision: 200970 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/72/1547205.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_1547205
loop_
_publ_author_name
'Adamovich, S. N.'
'Mirskova, A. N.'
'Mirskov, R. G.'
'Schilde, Uwe'
_publ_section_title
;
 Synthesis and Crystal Structure of
 1,4,10,13-Tetraoxa-7,16-diazoniumcyclo- octadecane
 bis(4-chloro-2-methyl-phenoxyacetate)
;
_journal_name_full               'Chemistry Central Journal20115:23'
_journal_page_first              23
_journal_paper_doi               10.1186/1752-153X-5-23
_journal_volume                  5
_journal_year                    2011
_chemical_formula_moiety         'C6 H14 N O2(+), C9 H8 Cl O3(-)'
_chemical_formula_sum            'C15 H22 Cl N O5'
_chemical_formula_weight         331.79
_chemical_melting_point          401
_chemical_name_systematic
; 
 1,4,10,13-Tetraoxa-7,16-diazoniumcyclo-
 octadecane bis(4-chloro-2-methyl-phenoxyacetate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.624(7)
_cell_angle_beta                 93.340(6)
_cell_angle_gamma                108.945(6)
_cell_formula_units_Z            2
_cell_length_a                   7.5342(6)
_cell_length_b                   9.1935(8)
_cell_length_c                   12.8532(10)
_cell_measurement_reflns_used    8906
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      1.61
_cell_volume                     829.73(12)
_computing_cell_refinement       'X-AREA (Stoe, 2004)'
_computing_data_collection       'X-AREA (Stoe, 2004)'
_computing_data_reduction        'X-RED (Stoe, 2004)'
_computing_molecular_graphics
;
 ORTEP-3 for Windows (Farrugia, 2005) based on ORTEP-III
 (Burnett & Johnson, 2000)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
 180 frames, detector distance = 140 mm
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'ω scan, 1.0 °'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5361
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          1.5
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0724P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.11110
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2280
_reflns_number_total             2738
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            13065_2011_284_MOESM1_ESM.CIF
_cod_data_source_block           mir1
_cod_database_code               1547205
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4555(2) 0.4163(2) 0.62428(13) 0.0315(4) Uani 1 1 d . . .
C2 C 0.2674(2) 0.3692(2) 0.58055(14) 0.0346(4) Uani 1 1 d . . .
C3 C 0.2013(2) 0.2405(2) 0.50211(14) 0.0393(4) Uani 1 1 d . . .
H3 H 0.078(3) 0.203(2) 0.4707(18) 0.052(6) Uiso 1 1 d . . .
C4 C 0.3186(3) 0.1607(2) 0.46627(15) 0.0406(4) Uani 1 1 d . . .
C5 C 0.5027(3) 0.2057(2) 0.50993(16) 0.0413(5) Uani 1 1 d . . .
H5 H 0.582(3) 0.150(3) 0.4909(18) 0.060(6) Uiso 1 1 d . . .
C6 C 0.5711(2) 0.3331(2) 0.59040(15) 0.0376(4) Uani 1 1 d . . .
H6 H 0.696(3) 0.363(2) 0.6210(16) 0.041(5) Uiso 1 1 d . . .
C7 C 0.7070(2) 0.6077(2) 0.73916(15) 0.0335(4) Uani 1 1 d . . .
H7A H 0.788(3) 0.613(2) 0.6826(16) 0.039(5) Uiso 1 1 d . . .
H7B H 0.725(2) 0.713(2) 0.7698(14) 0.031(4) Uiso 1 1 d . . .
C8 C 0.7661(2) 0.52341(18) 0.82198(13) 0.0285(4) Uani 1 1 d . . .
C9 C 0.1423(3) 0.4589(3) 0.61843(18) 0.0480(5) Uani 1 1 d . . .
H9A H 0.197(3) 0.574(3) 0.6085(19) 0.055(6) Uiso 1 1 d . . .
H9B H 0.128(3) 0.458(3) 0.693(2) 0.056(6) Uiso 1 1 d . . .
H9C H 0.025(4) 0.415(3) 0.580(2) 0.072(7) Uiso 1 1 d . . .
C10 C 0.6356(3) 1.18592(19) 1.16841(14) 0.0345(4) Uani 1 1 d . . .
H10A H 0.539(3) 1.186(2) 1.2136(17) 0.042(5) Uiso 1 1 d . . .
H10B H 0.755(3) 1.262(2) 1.2107(17) 0.047(5) Uiso 1 1 d . . .
C11 C 0.7300(3) 0.9907(2) 1.23382(15) 0.0381(4) Uani 1 1 d . . .
H11A H 0.846(3) 1.077(3) 1.2676(17) 0.052(6) Uiso 1 1 d . . .
H11B H 0.635(3) 0.960(2) 1.2807(17) 0.045(5) Uiso 1 1 d . . .
C12 C 0.7852(3) 0.8513(2) 1.19721(16) 0.0362(4) Uani 1 1 d . . .
H12A H 0.680(3) 0.766(3) 1.1563(18) 0.050(6) Uiso 1 1 d . . .
H12B H 0.820(3) 0.811(2) 1.2562(18) 0.046(6) Uiso 1 1 d . . .
C13 C 1.0015(2) 0.7734(2) 1.09967(16) 0.0354(4) Uani 1 1 d . . .
H13A H 1.024(3) 0.722(2) 1.1539(17) 0.039(5) Uiso 1 1 d . . .
H13B H 0.900(3) 0.692(2) 1.0516(16) 0.043(5) Uiso 1 1 d . . .
C14 C 1.1725(2) 0.8380(2) 1.04351(16) 0.0337(4) Uani 1 1 d . . .
H14A H 1.267(3) 0.902(3) 1.0911(18) 0.050(6) Uiso 1 1 d . . .
H14B H 1.146(3) 0.894(2) 0.9933(16) 0.033(5) Uiso 1 1 d . . .
C15 C 1.4023(2) 0.75799(19) 0.93222(14) 0.0316(4) Uani 1 1 d . . .
H15A H 1.435(2) 0.667(2) 0.9174(13) 0.026(4) Uiso 1 1 d . . .
H15B H 1.495(3) 0.837(2) 0.9778(15) 0.033(5) Uiso 1 1 d . . .
Cl1 Cl 0.23133(8) 0.00306(6) 0.36372(4) 0.0586(2) Uani 1 1 d . . .
N1 N 1.23201(19) 0.70945(16) 0.99114(11) 0.0277(3) Uani 1 1 d . . .
H1 H 1.252(3) 0.652(2) 1.0377(18) 0.041(5) Uiso 1 1 d . . .
H2 H 1.134(3) 0.638(2) 0.9441(18) 0.048(6) Uiso 1 1 d . . .
O1 O 0.51241(16) 0.54688(14) 0.69971(10) 0.0369(3) Uani 1 1 d . . .
O2 O 0.64311(18) 0.43458(17) 0.86564(12) 0.0521(4) Uani 1 1 d . . .
O3 O 0.94035(16) 0.55600(15) 0.84055(10) 0.0395(3) Uani 1 1 d . . .
O4 O 0.65449(16) 1.03664(13) 1.14495(9) 0.0316(3) Uani 1 1 d . . .
O5 O 0.93989(16) 0.89792(13) 1.13611(9) 0.0333(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'
Cl Cl 0.1484 0.1585 '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
O1 C1 C6 124.33(15) . .
O1 C1 C2 115.40(13) . .
C6 C1 C2 120.27(16) . .
C3 C2 C1 118.60(15) . .
C3 C2 C9 121.39(17) . .
C1 C2 C9 120.01(17) . .
C2 C3 C4 120.96(17) . .
C2 C3 H3 122.6(12) . .
C4 C3 H3 116.5(12) . .
C5 C4 C3 120.50(17) . .
C5 C4 Cl1 120.15(14) . .
C3 C4 Cl1 119.35(14) . .
C4 C5 C6 119.50(17) . .
C4 C5 H5 122.2(15) . .
C6 C5 H5 118.1(15) . .
C1 C6 C5 120.12(17) . .
C1 C6 H6 120.5(11) . .
C5 C6 H6 119.4(11) . .
O1 C7 C8 115.00(14) . .
O1 C7 H7A 111.7(12) . .
C8 C7 H7A 109.6(12) . .
O1 C7 H7B 103.8(11) . .
C8 C7 H7B 109.6(11) . .
H7A C7 H7B 106.7(16) . .
O2 C8 O3 126.33(16) . .
O2 C8 C7 119.17(14) . .
O3 C8 C7 114.48(15) . .
C2 C9 H9A 111.4(12) . .
C2 C9 H9B 111.7(13) . .
H9A C9 H9B 107.2(19) . .
C2 C9 H9C 109.1(15) . .
H9A C9 H9C 108(2) . .
H9B C9 H9C 109(2) . .
O4 C10 C15 109.71(13) . 2_777
O4 C10 H10A 112.1(12) . .
C15 C10 H10A 110.8(13) 2_777 .
O4 C10 H10B 109.8(11) . .
C15 C10 H10B 110.1(13) 2_777 .
H10A C10 H10B 104.2(17) . .
O4 C11 C12 108.92(15) . .
O4 C11 H11A 109.1(13) . .
C12 C11 H11A 107.9(12) . .
O4 C11 H11B 109.6(13) . .
C12 C11 H11B 107.4(12) . .
H11A C11 H11B 113.7(18) . .
O5 C12 C11 108.47(15) . .
O5 C12 H12A 110.5(13) . .
C11 C12 H12A 112.1(12) . .
O5 C12 H12B 110.0(13) . .
C11 C12 H12B 110.1(11) . .
H12A C12 H12B 105.6(18) . .
O5 C13 C14 107.27(14) . .
O5 C13 H13A 112.0(11) . .
C14 C13 H13A 113.0(12) . .
O5 C13 H13B 109.9(11) . .
C14 C13 H13B 111.1(12) . .
H13A C13 H13B 103.6(17) . .
N1 C14 C13 110.33(14) . .
N1 C14 H14A 109.1(14) . .
C13 C14 H14A 108.6(14) . .
N1 C14 H14B 109.7(11) . .
C13 C14 H14B 109.8(12) . .
H14A C14 H14B 109.3(19) . .
N1 C15 C10 113.09(14) . 2_777
N1 C15 H15A 104.5(11) . .
C10 C15 H15A 110.1(11) 2_777 .
N1 C15 H15B 106.7(11) . .
C10 C15 H15B 110.2(12) 2_777 .
H15A C15 H15B 112.2(16) . .
C14 N1 C15 115.90(13) . .
C14 N1 H1 110.5(12) . .
C15 N1 H1 108.5(14) . .
C14 N1 H2 111.3(12) . .
C15 N1 H2 107.4(13) . .
H1 N1 H2 102.4(19) . .
C1 O1 C7 117.34(12) . .
C11 O4 C10 112.78(13) . .
C13 O5 C12 111.91(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.369(2) .
C1 C6 1.387(2) .
C1 C2 1.398(2) .
C2 C3 1.381(3) .
C2 C9 1.502(2) .
C3 C4 1.382(3) .
C3 H3 0.93(2) .
C4 C5 1.373(3) .
C4 Cl1 1.7444(19) .
C5 C6 1.390(3) .
C5 H5 0.93(2) .
C6 H6 0.94(2) .
C7 O1 1.423(2) .
C7 C8 1.523(2) .
C7 H7A 0.97(2) .
C7 H7B 0.958(18) .
C8 O2 1.237(2) .
C8 O3 1.249(2) .
C9 H9A 1.03(2) .
C9 H9B 0.97(3) .
C9 H9C 0.93(3) .
C10 O4 1.420(2) .
C10 C15 1.500(3) 2_777
C10 H10A 0.96(2) .
C10 H10B 1.02(2) .
C11 O4 1.419(2) .
C11 C12 1.499(3) .
C11 H11A 1.00(2) .
C11 H11B 0.96(2) .
C12 O5 1.425(2) .
C12 H12A 0.98(2) .
C12 H12B 0.95(2) .
C13 O5 1.405(2) .
C13 C14 1.503(2) .
C13 H13A 0.93(2) .
C13 H13B 0.99(2) .
C14 N1 1.490(2) .
C14 H14A 0.90(2) .
C14 H14B 0.93(2) .
C15 N1 1.500(2) .
C15 C10 1.500(3) 2_777
C15 H15A 0.941(17) .
C15 H15B 0.93(2) .
N1 H1 0.89(2) .
N1 H2 0.93(2) .
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
N1 H2 O3 0.93(2) 1.81(2) 2.7078(18) 161(2) .
N1 H1 O2 0.89(2) 1.83(2) 2.698(2) 165(2) 2_767
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
O1 C1 C2 C3 178.46(15) . . . .
C6 C1 C2 C3 -1.2(3) . . . .
O1 C1 C2 C9 -1.0(3) . . . .
C6 C1 C2 C9 179.33(19) . . . .
C1 C2 C3 C4 -0.8(3) . . . .
C9 C2 C3 C4 178.7(2) . . . .
C2 C3 C4 C5 1.6(3) . . . .
C2 C3 C4 Cl1 -177.68(14) . . . .
C3 C4 C5 C6 -0.3(3) . . . .
Cl1 C4 C5 C6 178.95(15) . . . .
O1 C1 C6 C5 -177.16(16) . . . .
C2 C1 C6 C5 2.4(3) . . . .
C4 C5 C6 C1 -1.7(3) . . . .
O1 C7 C8 O2 -15.4(2) . . . .
O1 C7 C8 O3 166.31(14) . . . .
O4 C11 C12 O5 67.19(19) . . . .
O5 C13 C14 N1 -173.03(15) . . . .
C13 C14 N1 C15 -179.80(15) . . . .
C10 C15 N1 C14 -72.10(19) 2_777 . . .
C6 C1 O1 C7 5.5(2) . . . .
C2 C1 O1 C7 -174.16(16) . . . .
C8 C7 O1 C1 -79.74(19) . . . .
C12 C11 O4 C10 -167.40(15) . . . .
C15 C10 O4 C11 167.28(14) 2_777 . . .
C14 C13 O5 C12 -175.94(15) . . . .
C11 C12 O5 C13 179.36(16) . . . .
