# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_[(DPA)([18]crown-6)]ClO4(293K)
_database_code_depnum_ccdc_archive 'CCDC 1028137'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Dipropylammonium perchlorate 18-crown-6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, Cl O4, C6 H16 N'
_chemical_formula_sum            'C18 H40 Cl N O10'
_chemical_formula_weight         465.96

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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   16.5769(4)
_cell_length_b                   15.1415(3)
_cell_length_c                   10.0908(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2532.78(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7207
_exptl_absorpt_correction_T_max  0.7207
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8168
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         74.49
_reflns_number_total             2620
_reflns_number_gt                2080
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.6707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5000 0.0000 0.5000 0.0737(3) Uani 1 2 d S . .
O4 O 0.10116(12) 0.2500 0.64568(17) 0.0666(5) Uani 1 2 d S . .
O2 O 0.24068(8) 0.09046(8) 0.30501(13) 0.0617(4) Uani 1 1 d . . .
O3 O 0.16886(8) 0.08551(9) 0.56109(15) 0.0677(4) Uani 1 1 d . . .
N1 N 0.30944(12) 0.2500 0.4210(2) 0.0557(5) Uani 1 2 d S . .
H4A H 0.2820 0.2991 0.3916 0.067 Uiso 0.50 1 calc PR . .
H4B H 0.2820 0.2009 0.3916 0.067 Uiso 0.50 1 calc PR . .
C1 C 0.18457(15) 0.17252(16) 0.1279(2) 0.0750(6) Uani 1 1 d . . .
H5A H 0.2362 0.1674 0.0792 0.090 Uiso 1 1 calc R . .
H5B H 0.1401 0.1745 0.0625 0.090 Uiso 1 1 calc R . .
C6 C 0.10315(15) 0.17261(17) 0.7241(2) 0.0801(7) Uani 1 1 d . . .
H6A H 0.0575 0.1731 0.7873 0.096 Uiso 1 1 calc R . .
H6B H 0.1539 0.1708 0.7757 0.096 Uiso 1 1 calc R . .
C3 C 0.23847(15) 0.01360(13) 0.3868(3) 0.0795(6) Uani 1 1 d . . .
H7A H 0.2886 0.0112 0.4400 0.095 Uiso 1 1 calc R . .
H7B H 0.2374 -0.0393 0.3293 0.095 Uiso 1 1 calc R . .
C5 C 0.09777(14) 0.09362(16) 0.6382(2) 0.0805(7) Uani 1 1 d . . .
H8A H 0.0908 0.0402 0.6936 0.097 Uiso 1 1 calc R . .
H8B H 0.0503 0.0988 0.5791 0.097 Uiso 1 1 calc R . .
C2 C 0.17408(14) 0.09604(15) 0.2173(2) 0.0756(6) Uani 1 1 d . . .
H9A H 0.1236 0.1028 0.2686 0.091 Uiso 1 1 calc R . .
H9B H 0.1701 0.0411 0.1645 0.091 Uiso 1 1 calc R . .
C9 C 0.39295(19) 0.2500 0.3615(3) 0.0789(9) Uani 1 2 d S . .
H10A H 0.4223 0.3028 0.3937 0.095 Uiso 0.50 1 calc PR . .
H10B H 0.4223 0.1972 0.3937 0.095 Uiso 0.50 1 calc PR . .
C4 C 0.16789(17) 0.01012(13) 0.4785(3) 0.0819(7) Uani 1 1 d . . .
H11A H 0.1172 0.0086 0.4267 0.098 Uiso 1 1 calc R . .
H11B H 0.1706 -0.0441 0.5332 0.098 Uiso 1 1 calc R . .
C10 C 0.3098(2) 0.2500 0.5671(3) 0.1090(19) Uani 1 2 d S . .
C8 C 0.3947(2) 0.2500 0.2167(3) 0.0923(11) Uani 1 2 d S . .
H14A H 0.3656 0.3028 0.1840 0.111 Uiso 0.50 1 calc PR . .
H14B H 0.3656 0.1972 0.1840 0.111 Uiso 0.50 1 calc PR . .
C7 C 0.4766(3) 0.2500 0.1618(5) 0.154(3) Uani 1 2 d S . .
H15B H 0.4739 0.2500 0.0648 0.147(17) Uiso 1 2 d SR . .
H15C H 0.5055 0.1973 0.1924 0.28(3) Uiso 1 1 d R . .
C11 C 0.3533(3) 0.2057(3) 0.6481(4) 0.0704(11) Uani 0.50 1 d P . .
C12 C 0.3552(3) 0.2500 0.7922(4) 0.1226(18) Uani 1 2 d S . .
O1 O 0.18433(11) 0.2500 0.20529(16) 0.0582(4) Uani 1 2 d S . .
O8 O 0.57778(18) 0.0029(3) 0.5416(4) 0.0937(11) Uani 0.50 1 d P . .
O6 O 0.4644(3) -0.0802(3) 0.4943(4) 0.1040(13) Uani 0.50 1 d P . .
O7 O 0.4515(2) 0.0532(3) 0.6049(6) 0.1287(17) Uani 0.50 1 d P . .
O5 O 0.4896(3) 0.0504(4) 0.3800(6) 0.147(2) Uani 0.50 1 d P . .
H2 H 0.3216 0.1895 0.5421 0.19(4) Uiso 0.50 1 d PR . .
H3 H 0.2537(15) 0.2500 0.571(2) 0.149(18) Uiso 1 2 d S . .
H6 H 0.4121 0.1909 0.6042 0.107(17) Uiso 0.50 1 d PR . .
H7 H 0.3305 0.1511 0.6499 0.099(18) Uiso 0.50 1 d PR . .
H1 H 0.3095 0.2500 0.8218 0.119(17) Uiso 1 2 d SR . .
H4 H 0.3843 0.2013 0.8216 0.146(14) Uiso 1 1 d R . .


_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
Cl1 O6 1.352(3) 5_656 ?
Cl1 O6 1.352(3) . ?
Cl1 O8 1.357(3) 5_656 ?
Cl1 O8 1.357(3) . ?
Cl1 O5 1.442(5) . ?
Cl1 O5 1.442(5) 5_656 ?
Cl1 O7 1.554(4) 5_656 ?
Cl1 O7 1.554(4) . ?
O4 C6 1.415(2) 8_565 ?
O4 C6 1.415(2) . ?
O2 C2 1.418(2) . ?
O2 C3 1.427(3) . ?
O3 C4 1.414(3) . ?
O3 C5 1.417(3) . ?
N1 C10 1.474(4) . ?
N1 C9 1.509(4) . ?
C1 O1 1.409(2) . ?
C1 C2 1.478(3) . ?
C6 C5 1.480(3) . ?
C3 C4 1.492(4) . ?
C9 C8 1.461(5) . ?
C10 C11 1.280(5) 8_565 ?
C10 C11 1.280(5) . ?
C8 C7 1.467(5) . ?
C11 C11 1.341(9) 8_565 ?
C11 C12 1.602(5) . ?
C12 C11 1.602(5) 8_565 ?
O1 C1 1.409(2) 8_565 ?
O8 O6 1.411(5) 5_656 ?
O8 O5 1.590(6) 5_656 ?
O8 O7 1.773(6) 5_656 ?
O6 O8 1.411(5) 5_656 ?
O6 O5 1.547(6) 5_656 ?
O6 O7 1.764(5) 5_656 ?
O7 O6 1.764(5) 5_656 ?
O7 O8 1.773(6) 5_656 ?
O5 O6 1.547(6) 5_656 ?
O5 O8 1.590(6) 5_656 ?

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
O6 Cl1 O6 180.0(3) 5_656 . ?
O6 Cl1 O8 117.2(2) 5_656 5_656 ?
O6 Cl1 O8 62.8(2) . 5_656 ?
O6 Cl1 O8 62.8(2) 5_656 . ?
O6 Cl1 O8 117.2(2) . . ?
O8 Cl1 O8 180.0(3) 5_656 . ?
O6 Cl1 O5 67.1(3) 5_656 . ?
O6 Cl1 O5 112.9(3) . . ?
O8 Cl1 O5 69.2(2) 5_656 . ?
O8 Cl1 O5 110.8(2) . . ?
O6 Cl1 O5 112.9(3) 5_656 5_656 ?
O6 Cl1 O5 67.1(3) . 5_656 ?
O8 Cl1 O5 110.8(2) 5_656 5_656 ?
O8 Cl1 O5 69.2(2) . 5_656 ?
O5 Cl1 O5 180.0(4) . 5_656 ?
O6 Cl1 O7 105.6(2) 5_656 5_656 ?
O6 Cl1 O7 74.4(2) . 5_656 ?
O8 Cl1 O7 105.3(2) 5_656 5_656 ?
O8 Cl1 O7 74.7(2) . 5_656 ?
O5 Cl1 O7 76.4(4) . 5_656 ?
O5 Cl1 O7 103.6(4) 5_656 5_656 ?
O6 Cl1 O7 74.4(2) 5_656 . ?
O6 Cl1 O7 105.6(2) . . ?
O8 Cl1 O7 74.7(2) 5_656 . ?
O8 Cl1 O7 105.3(2) . . ?
O5 Cl1 O7 103.6(4) . . ?
O5 Cl1 O7 76.4(4) 5_656 . ?
O7 Cl1 O7 180.0(3) 5_656 . ?
C6 O4 C6 111.9(2) 8_565 . ?
C2 O2 C3 112.95(16) . . ?
C4 O3 C5 112.59(17) . . ?
C10 N1 C9 113.3(2) . . ?
O1 C1 C2 108.29(16) . . ?
O4 C6 C5 109.87(17) . . ?
O2 C3 C4 114.04(17) . . ?
O3 C5 C6 109.97(18) . . ?
O2 C2 C1 109.65(17) . . ?
C8 C9 N1 114.6(3) . . ?
O3 C4 C3 109.14(18) . . ?
C11 C10 C11 63.2(4) 8_565 . ?
C11 C10 N1 129.8(3) 8_565 . ?
C11 C10 N1 129.8(3) . . ?
C9 C8 C7 113.3(3) . . ?
C10 C11 C11 58.4(2) . 8_565 ?
C10 C11 C12 111.8(3) . . ?
C11 C11 C12 65.27(17) 8_565 . ?
C11 C12 C11 49.5(3) 8_565 . ?
C1 O1 C1 112.7(2) 8_565 . ?
Cl1 O8 O6 58.4(2) . 5_656 ?
Cl1 O8 O5 57.9(2) . 5_656 ?
O6 O8 O5 101.6(3) 5_656 5_656 ?
Cl1 O8 O7 57.73(17) . 5_656 ?
O6 O8 O7 92.7(3) 5_656 5_656 ?
O5 O8 O7 88.8(3) 5_656 5_656 ?
Cl1 O6 O8 58.8(2) . 5_656 ?
Cl1 O6 O5 59.2(2) . 5_656 ?
O8 O6 O5 102.3(3) 5_656 5_656 ?
Cl1 O6 O7 58.07(17) . 5_656 ?
O8 O6 O7 93.1(3) 5_656 5_656 ?
O5 O6 O7 90.5(3) 5_656 5_656 ?
Cl1 O7 O6 47.56(16) . 5_656 ?
Cl1 O7 O8 47.57(16) . 5_656 ?
O6 O7 O8 81.6(3) 5_656 5_656 ?
Cl1 O5 O6 53.6(2) . 5_656 ?
Cl1 O5 O8 52.9(2) . 5_656 ?
O6 O5 O8 94.9(3) 5_656 5_656 ?

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
C6 O4 C6 C5 177.82(13) 8_565 . . . ?
C2 O2 C3 C4 -63.1(3) . . . . ?
C4 O3 C5 C6 178.93(18) . . . . ?
O4 C6 C5 O3 67.9(2) . . . . ?
C3 O2 C2 C1 -174.80(17) . . . . ?
O1 C1 C2 O2 -63.4(2) . . . . ?
C10 N1 C9 C8 180.0 . . . . ?
C5 O3 C4 C3 171.65(19) . . . . ?
O2 C3 C4 O3 -58.5(3) . . . . ?
C9 N1 C10 C11 43.0(4) . . . 8_565 ?
C9 N1 C10 C11 -43.0(4) . . . . ?
N1 C9 C8 C7 180.0 . . . . ?
N1 C10 C11 C11 120.9(4) . . . 8_565 ?
C11 C10 C11 C12 39.2(4) 8_565 . . . ?
N1 C10 C11 C12 160.0(3) . . . . ?
C10 C11 C12 C11 -36.3(4) . . . 8_565 ?
C2 C1 O1 C1 -173.07(13) . . . 8_565 ?
O6 Cl1 O8 O6 180.0 . . . 5_656 ?
O8 Cl1 O8 O6 -104(10) 5_656 . . 5_656 ?
O5 Cl1 O8 O6 48.5(4) . . . 5_656 ?
O5 Cl1 O8 O6 -131.5(4) 5_656 . . 5_656 ?
O7 Cl1 O8 O6 117.0(3) 5_656 . . 5_656 ?
O7 Cl1 O8 O6 -63.0(3) . . . 5_656 ?
O6 Cl1 O8 O5 131.5(4) 5_656 . . 5_656 ?
O6 Cl1 O8 O5 -48.5(4) . . . 5_656 ?
O8 Cl1 O8 O5 27(15) 5_656 . . 5_656 ?
O5 Cl1 O8 O5 180.0 . . . 5_656 ?
O7 Cl1 O8 O5 -111.4(4) 5_656 . . 5_656 ?
O7 Cl1 O8 O5 68.6(4) . . . 5_656 ?
O6 Cl1 O8 O7 -117.0(3) 5_656 . . 5_656 ?
O6 Cl1 O8 O7 63.0(3) . . . 5_656 ?
O8 Cl1 O8 O7 139(12) 5_656 . . 5_656 ?
O5 Cl1 O8 O7 -68.6(4) . . . 5_656 ?
O5 Cl1 O8 O7 111.4(4) 5_656 . . 5_656 ?
O7 Cl1 O8 O7 180.0 . . . 5_656 ?
O6 Cl1 O6 O8 44(80) 5_656 . . 5_656 ?
O8 Cl1 O6 O8 180.0 . . . 5_656 ?
O5 Cl1 O6 O8 -49.4(4) . . . 5_656 ?
O5 Cl1 O6 O8 130.6(4) 5_656 . . 5_656 ?
O7 Cl1 O6 O8 -116.9(3) 5_656 . . 5_656 ?
O7 Cl1 O6 O8 63.1(3) . . . 5_656 ?
O6 Cl1 O6 O5 -87(80) 5_656 . . 5_656 ?
O8 Cl1 O6 O5 -130.6(4) 5_656 . . 5_656 ?
O8 Cl1 O6 O5 49.4(4) . . . 5_656 ?
O5 Cl1 O6 O5 180.0 . . . 5_656 ?
O7 Cl1 O6 O5 112.6(4) 5_656 . . 5_656 ?
O7 Cl1 O6 O5 -67.4(4) . . . 5_656 ?
O6 Cl1 O6 O7 161(80) 5_656 . . 5_656 ?
O8 Cl1 O6 O7 116.9(3) 5_656 . . 5_656 ?
O8 Cl1 O6 O7 -63.1(3) . . . 5_656 ?
O5 Cl1 O6 O7 67.4(4) . . . 5_656 ?
O5 Cl1 O6 O7 -112.6(4) 5_656 . . 5_656 ?
O7 Cl1 O6 O7 180.0 . . . 5_656 ?
O6 Cl1 O7 O6 180.0 . . . 5_656 ?
O8 Cl1 O7 O6 -124.6(3) 5_656 . . 5_656 ?
O8 Cl1 O7 O6 55.4(3) . . . 5_656 ?
O5 Cl1 O7 O6 -61.1(3) . . . 5_656 ?
O5 Cl1 O7 O6 118.9(3) 5_656 . . 5_656 ?
O7 Cl1 O7 O6 133(100) 5_656 . . 5_656 ?
O6 Cl1 O7 O8 124.6(3) 5_656 . . 5_656 ?
O6 Cl1 O7 O8 -55.4(3) . . . 5_656 ?
O8 Cl1 O7 O8 180.0 . . . 5_656 ?
O5 Cl1 O7 O8 63.5(3) . . . 5_656 ?
O5 Cl1 O7 O8 -116.5(3) 5_656 . . 5_656 ?
O7 Cl1 O7 O8 -103(100) 5_656 . . 5_656 ?
O6 Cl1 O5 O6 180.0 . . . 5_656 ?
O8 Cl1 O5 O6 133.7(3) 5_656 . . 5_656 ?
O8 Cl1 O5 O6 -46.3(3) . . . 5_656 ?
O5 Cl1 O5 O6 45(100) 5_656 . . 5_656 ?
O7 Cl1 O5 O6 -113.8(3) 5_656 . . 5_656 ?
O7 Cl1 O5 O6 66.2(3) . . . 5_656 ?
O6 Cl1 O5 O8 -133.7(3) 5_656 . . 5_656 ?
O6 Cl1 O5 O8 46.3(3) . . . 5_656 ?
O8 Cl1 O5 O8 180.0 . . . 5_656 ?
O5 Cl1 O5 O8 -88(100) 5_656 . . 5_656 ?
O7 Cl1 O5 O8 112.5(3) 5_656 . . 5_656 ?
O7 Cl1 O5 O8 -67.5(3) . . . 5_656 ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        74.49
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.032
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_[(DPA)([18]crown-6)]ClO4(100K)
_database_code_depnum_ccdc_archive 'CCDC 1028138'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Dipropylammonium perchlorate 18-crown-6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, C6 H16 N, Cl O4'
_chemical_formula_sum            'C18 H40 Cl N O10'
_chemical_formula_weight         465.96

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.031(6)
_cell_length_b                   15.109(9)
_cell_length_c                   16.199(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2455(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18956
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5591
_reflns_number_gt                4694
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0728P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.31(7)
_refine_ls_number_reflns         5591
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.98744(6) 0.77025(4) 0.23735(4) 0.02313(15) Uani 1 1 d . . .
O1 O 1.68581(16) 0.33436(10) 0.01677(11) 0.0221(4) Uani 1 1 d . . .
O2 O 1.79824(16) 0.49345(10) 0.06718(11) 0.0219(4) Uani 1 1 d . . .
O3 O 1.70777(16) 0.65298(10) 0.00186(10) 0.0210(4) Uani 1 1 d . . .
O5 O 1.35819(17) 0.51457(11) 0.15605(12) 0.0273(4) Uani 1 1 d . . .
O6 O 1.43168(17) 0.34468(11) 0.08926(12) 0.0277(4) Uani 1 1 d . . .
O4 O 1.45120(17) 0.67355(11) 0.07902(11) 0.0256(4) Uani 1 1 d . . .
N1 N 1.57644(19) 0.49430(13) -0.05695(13) 0.0204(4) Uani 1 1 d . . .
H1A H 1.6220 0.5413 -0.0344 0.024 Uiso 1 1 calc R . .
H1B H 1.5917 0.4457 -0.0241 0.024 Uiso 1 1 calc R . .
C11 C 1.8675(2) 0.41202(16) 0.07559(18) 0.0254(6) Uani 1 1 d . . .
H11A H 1.9291 0.4149 0.1233 0.031 Uiso 1 1 calc R . .
H11B H 1.9205 0.4001 0.0253 0.031 Uiso 1 1 calc R . .
C2 C 1.5011(3) 0.26283(16) 0.08997(16) 0.0264(5) Uani 1 1 d . . .
H2A H 1.4370 0.2132 0.0855 0.032 Uiso 1 1 calc R . .
H2B H 1.5508 0.2563 0.1424 0.032 Uiso 1 1 calc R . .
C1 C 1.5959(3) 0.26079(17) 0.01857(17) 0.0262(6) Uani 1 1 d . . .
H1 H 1.6484 0.2054 0.0211 0.031 Uiso 1 1 calc R . .
H2 H 1.5440 0.2600 -0.0334 0.031 Uiso 1 1 calc R . .
C10 C 1.8853(2) 0.56673(16) 0.05819(17) 0.0244(6) Uani 1 1 d . . .
H10A H 1.9288 0.5650 0.0034 0.029 Uiso 1 1 calc R . .
H10B H 1.9554 0.5649 0.1011 0.029 Uiso 1 1 calc R . .
C4 C 1.2749(3) 0.43863(18) 0.15618(19) 0.0326(6) Uani 1 1 d . . .
H4A H 1.2224 0.4367 0.1044 0.039 Uiso 1 1 calc R . .
H4B H 1.2118 0.4421 0.2031 0.039 Uiso 1 1 calc R . .
O9 O 0.95286(18) 0.76627(14) 0.32287(11) 0.0325(4) Uani 1 1 d . . .
O7 O 1.0050(2) 0.68225(12) 0.20639(12) 0.0387(5) Uani 1 1 d . . .
C8 C 1.6329(3) 0.73328(16) 0.00245(17) 0.0265(5) Uani 1 1 d . . .
H8A H 1.5772 0.7356 -0.0480 0.032 Uiso 1 1 calc R . .
H8B H 1.6956 0.7838 0.0003 0.032 Uiso 1 1 calc R . .
C9 C 1.8043(2) 0.64975(15) 0.06675(16) 0.0221(5) Uani 1 1 d . . .
H9A H 1.7588 0.6504 0.1210 0.027 Uiso 1 1 calc R . .
H9B H 1.8634 0.7021 0.0636 0.027 Uiso 1 1 calc R . .
C7 C 1.5440(2) 0.74400(15) 0.07672(16) 0.0259(6) Uani 1 1 d . . .
H7A H 1.5985 0.7438 0.1277 0.031 Uiso 1 1 calc R . .
H7B H 1.4962 0.8012 0.0735 0.031 Uiso 1 1 calc R . .
C12 C 1.7681(2) 0.34012(16) 0.08836(17) 0.0263(6) Uani 1 1 d . . .
H12A H 1.8144 0.2831 0.0976 0.032 Uiso 1 1 calc R . .
H12B H 1.7128 0.3532 0.1375 0.032 Uiso 1 1 calc R . .
C15 C 1.6307(2) 0.47631(17) -0.14094(16) 0.0249(6) Uani 1 1 d . . .
H15A H 1.5894 0.5176 -0.1809 0.030 Uiso 1 1 calc R . .
H15B H 1.6066 0.4153 -0.1575 0.030 Uiso 1 1 calc R . .
C14 C 1.7806(3) 0.48662(18) -0.14415(17) 0.0276(6) Uani 1 1 d . . .
H14A H 1.8221 0.4495 -0.1008 0.033 Uiso 1 1 calc R . .
H14B H 1.8048 0.5491 -0.1333 0.033 Uiso 1 1 calc R . .
C16 C 1.4291(2) 0.51500(17) -0.05595(18) 0.0239(6) Uani 1 1 d . . .
H16A H 1.3995 0.5210 0.0021 0.029 Uiso 1 1 calc R . .
H16B H 1.4144 0.5726 -0.0836 0.029 Uiso 1 1 calc R . .
C5 C 1.2824(3) 0.59423(18) 0.15241(18) 0.0313(6) Uani 1 1 d . . .
H5A H 1.2212 0.5973 0.2002 0.038 Uiso 1 1 calc R . .
H5B H 1.2283 0.5951 0.1013 0.038 Uiso 1 1 calc R . .
C3 C 1.3568(3) 0.35659(18) 0.16345(18) 0.0318(6) Uani 1 1 d . . .
H3A H 1.4181 0.3616 0.2111 0.038 Uiso 1 1 calc R . .
H3B H 1.2980 0.3049 0.1726 0.038 Uiso 1 1 calc R . .
O10 O 0.8822(2) 0.81308(13) 0.19253(13) 0.0389(5) Uani 1 1 d . . .
C17 C 1.3446(2) 0.44591(18) -0.09782(18) 0.0283(6) Uani 1 1 d . . .
H17A H 1.3512 0.3894 -0.0672 0.034 Uiso 1 1 calc R . .
H17B H 1.3779 0.4359 -0.1546 0.034 Uiso 1 1 calc R . .
C6 C 1.3753(3) 0.67241(18) 0.15346(17) 0.0304(6) Uani 1 1 d . . .
H6A H 1.3232 0.7278 0.1584 0.036 Uiso 1 1 calc R . .
H6B H 1.4358 0.6683 0.2016 0.036 Uiso 1 1 calc R . .
C13 C 1.8332(3) 0.4589(2) -0.22864(19) 0.0425(8) Uani 1 1 d . . .
H13A H 1.8170 0.3956 -0.2369 0.064 Uiso 1 1 calc R . .
H13B H 1.9291 0.4707 -0.2316 0.064 Uiso 1 1 calc R . .
H13C H 1.7872 0.4927 -0.2717 0.064 Uiso 1 1 calc R . .
O8 O 1.1096(2) 0.81904(16) 0.22795(15) 0.0497(6) Uani 1 1 d . . .
C18 C 1.1993(3) 0.4755(2) -0.1011(2) 0.0399(8) Uani 1 1 d . . .
H18A H 1.1653 0.4829 -0.0448 0.060 Uiso 1 1 calc R . .
H18B H 1.1462 0.4307 -0.1300 0.060 Uiso 1 1 calc R . .
H18C H 1.1931 0.5320 -0.1307 0.060 Uiso 1 1 calc R . .


_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
Cl1 O9 1.429(2) . ?
Cl1 O7 1.4319(19) . ?
Cl1 O10 1.436(2) . ?
Cl1 O8 1.438(2) . ?
O1 C12 1.426(3) . ?
O1 C1 1.431(3) . ?
O2 C10 1.417(3) . ?
O2 C11 1.419(3) . ?
O3 C8 1.427(3) . ?
O3 C9 1.430(3) . ?
O5 C4 1.419(3) . ?
O5 C5 1.425(3) . ?
O6 C2 1.419(3) . ?
O6 C3 1.429(3) . ?
O4 C7 1.415(3) . ?
O4 C6 1.426(3) . ?
N1 C15 1.490(3) . ?
N1 C16 1.511(3) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
C11 C12 1.489(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C1 1.498(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C10 C9 1.501(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C4 C3 1.492(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C7 1.506(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 C14 1.512(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 C13 1.525(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C17 1.506(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C5 C6 1.504(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C17 C18 1.525(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
O9 Cl1 O7 109.28(13) . . ?
O9 Cl1 O10 109.30(12) . . ?
O7 Cl1 O10 109.39(13) . . ?
O9 Cl1 O8 109.32(13) . . ?
O7 Cl1 O8 109.50(14) . . ?
O10 Cl1 O8 110.02(14) . . ?
C12 O1 C1 113.29(18) . . ?
C10 O2 C11 112.68(18) . . ?
C8 O3 C9 112.36(18) . . ?
C4 O5 C5 111.66(19) . . ?
C2 O6 C3 111.16(19) . . ?
C7 O4 C6 112.51(19) . . ?
C15 N1 C16 113.9(2) . . ?
C15 N1 H1A 108.8 . . ?
C16 N1 H1A 108.8 . . ?
C15 N1 H1B 108.8 . . ?
C16 N1 H1B 108.8 . . ?
H1A N1 H1B 107.7 . . ?
O2 C11 C12 108.56(19) . . ?
O2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O6 C2 C1 108.9(2) . . ?
O6 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
O6 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O1 C1 C2 113.6(2) . . ?
O1 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
O1 C1 H2 108.9 . . ?
C2 C1 H2 108.9 . . ?
H1 C1 H2 107.7 . . ?
O2 C10 C9 108.1(2) . . ?
O2 C10 H10A 110.1 . . ?
C9 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O5 C4 C3 110.3(2) . . ?
O5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
O5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
O3 C8 C7 114.1(2) . . ?
O3 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
O3 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O3 C9 C10 109.08(19) . . ?
O3 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O3 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O4 C7 C8 109.3(2) . . ?
O4 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
O4 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O1 C12 C11 108.6(2) . . ?
O1 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O1 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
N1 C15 C14 112.1(2) . . ?
N1 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C14 C13 110.3(2) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C17 C16 N1 113.7(2) . . ?
C17 C16 H16A 108.8 . . ?
N1 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
N1 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
O5 C5 C6 109.4(2) . . ?
O5 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
O5 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O6 C3 C4 109.1(2) . . ?
O6 C3 H3A 109.9 . . ?
C4 C3 H3A 109.9 . . ?
O6 C3 H3B 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C16 C17 C18 110.5(2) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O4 C6 C5 109.3(2) . . ?
O4 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
O4 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C10 O2 C11 C12 177.5(2) . . . . ?
C3 O6 C2 C1 -170.1(2) . . . . ?
C12 O1 C1 C2 60.1(3) . . . . ?
O6 C2 C1 O1 55.0(3) . . . . ?
C11 O2 C10 C9 -168.9(2) . . . . ?
C5 O5 C4 C3 -177.7(2) . . . . ?
C9 O3 C8 C7 -66.4(3) . . . . ?
C8 O3 C9 C10 -175.9(2) . . . . ?
O2 C10 C9 O3 -62.4(3) . . . . ?
C6 O4 C7 C8 172.1(2) . . . . ?
O3 C8 C7 O4 -60.2(3) . . . . ?
C1 O1 C12 C11 173.5(2) . . . . ?
O2 C11 C12 O1 62.9(3) . . . . ?
C16 N1 C15 C14 160.6(2) . . . . ?
N1 C15 C14 C13 174.5(2) . . . . ?
C15 N1 C16 C17 53.8(3) . . . . ?
C4 O5 C5 C6 179.3(2) . . . . ?
C2 O6 C3 C4 -174.2(2) . . . . ?
O5 C4 C3 O6 -68.6(3) . . . . ?
N1 C16 C17 C18 -174.8(2) . . . . ?
C7 O4 C6 C5 -178.2(2) . . . . ?
O5 C5 C6 O4 66.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.138
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(DPA)(ClO4)(273K)
_database_code_depnum_ccdc_archive 'CCDC 1028139'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Dipropylammonium)(ClO4)
_chemical_melting_point          ?
_chemical_formula_moiety         'Cl O4, C6 H16 N'
_chemical_formula_sum            'C6 H16 Cl N O4'
_chemical_formula_weight         201.65

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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C m c m'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.3536(11)
_cell_length_b                   8.6485(5)
_cell_length_c                   7.7268(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1092.83(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41364
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1695
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.79
_diffrn_reflns_theta_max         71.54
_reflns_number_total             601
_reflns_number_gt                530
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1491P)²+0.5612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         601
_refine_ls_number_parameters     53
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.2089
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.0000 0.71837(14) 0.2500 0.0651(8) Uani 1 4 d S . .
N2 N 0.0000 0.2889(4) 0.2500 0.0540(13) Uani 1 4 d S . .
H2A H 0.0000 0.3518 0.1539 0.065 Uiso 0.50 2 calc SPR . .
H2B H 0.0000 0.3518 0.3461 0.065 Uiso 0.50 2 calc SPR . .
C3 C -0.0759(3) 0.1961(5) 0.2500 0.0743(14) Uani 1 2 d S . .
H3A H -0.0763 0.1286 0.1465 0.089 Uiso 0.50 1 calc PR . .
H3B H -0.0763 0.1286 0.3535 0.089 Uiso 0.50 1 calc PR . .
C1 C -0.1507(4) 0.2915(7) 0.2500 0.097(2) Uani 1 2 d S . .
H1A H -0.1510 0.3588 0.1463 0.116 Uiso 0.50 1 calc PR . .
H1B H -0.1510 0.3588 0.3537 0.116 Uiso 0.50 1 calc PR . .
O2 O 0.0000 0.616(2) 0.108(2) 0.070(13) Uani 0.26(7) 2 d SPU A 1
O3 O -0.0617(7) 0.8152(8) 0.2500 0.249(5) Uani 1 2 d SU A .
C4 C -0.2272(6) 0.1904(17) 0.2500 0.159(5) Uani 1 2 d S . .
H4A H -0.2271 0.1246 0.1468 0.9(8) Uiso 0.50 1 d PR . .
H4B H -0.2760 0.2561 0.2500 0.18(5) Uiso 1 2 d SR . .
H4C H -0.2274 0.1254 0.3539 0.08(3) Uiso 0.50 1 d PR . .
O1 O -0.041(2) 0.6258(19) 0.119(2) 0.107(6) Uani 0.37(4) 1 d PU . 2


_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
Cl1 O3 1.312(8) . ?
Cl1 O3 1.312(8) 11 ?
Cl1 O2 1.41(2) 10_556 ?
Cl1 O2 1.41(2) . ?
Cl1 O1 1.455(10) 4 ?
Cl1 O1 1.455(10) 10_556 ?
Cl1 O1 1.455(10) . ?
Cl1 O1 1.455(10) 11 ?
N2 C3 1.478(5) 11 ?
N2 C3 1.478(5) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C3 C1 1.475(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 C4 1.527(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O1 O1 1.35(7) 11 ?

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
O3 Cl1 O3 100.6(9) . 11 ?
O3 Cl1 O2 113.6(5) . 10_556 ?
O3 Cl1 O2 113.6(5) 11 10_556 ?
O3 Cl1 O2 113.6(5) . . ?
O3 Cl1 O2 113.6(5) 11 . ?
O2 Cl1 O2 102.4(15) 10_556 . ?
O3 Cl1 O1 135.1(11) . 4 ?
O3 Cl1 O1 89.7(14) 11 4 ?
O2 Cl1 O1 27.6(15) 10_556 4 ?
O2 Cl1 O1 101.3(5) . 4 ?
O3 Cl1 O1 89.7(14) . 10_556 ?
O3 Cl1 O1 135.1(11) 11 10_556 ?
O2 Cl1 O1 27.6(15) 10_556 10_556 ?
O2 Cl1 O1 101.3(5) . 10_556 ?
O1 Cl1 O1 55(3) 4 10_556 ?
O3 Cl1 O1 89.7(14) . . ?
O3 Cl1 O1 135.1(11) 11 . ?
O2 Cl1 O1 101.3(5) 10_556 . ?
O2 Cl1 O1 27.6(15) . . ?
O1 Cl1 O1 113.2(14) 4 . ?
O1 Cl1 O1 88.0(16) 10_556 . ?
O3 Cl1 O1 135.1(11) . 11 ?
O3 Cl1 O1 89.7(14) 11 11 ?
O2 Cl1 O1 101.3(5) 10_556 11 ?
O2 Cl1 O1 27.6(15) . 11 ?
O1 Cl1 O1 88.0(16) 4 11 ?
O1 Cl1 O1 113.2(14) 10_556 11 ?
O1 Cl1 O1 55(3) . 11 ?
C3 N2 C3 114.2(4) 11 . ?
C3 N2 H2A 108.7 11 . ?
C3 N2 H2A 108.7 . . ?
C3 N2 H2B 108.7 11 . ?
C3 N2 H2B 108.7 . . ?
H2A N2 H2B 107.6 . . ?
C1 C3 N2 113.1(4) . . ?
C1 C3 H3A 109.0 . . ?
N2 C3 H3A 109.0 . . ?
C1 C3 H3B 109.0 . . ?
N2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C1 C4 111.0(7) . . ?
C3 C1 H1A 109.4 . . ?
C4 C1 H1A 109.4 . . ?
C3 C1 H1B 109.4 . . ?
C4 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C1 C4 H4A 109.4 . . ?
C1 C4 H4B 109.6 . . ?
H4A C4 H4B 109.7 . . ?
C1 C4 H4C 109.4 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.2 . . ?
O1 O1 Cl1 62.4(15) 11 . ?

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
C3 N2 C3 C1 180.0 11 . . . ?
N2 C3 C1 C4 180.0 . . . . ?
O3 Cl1 O1 O1 150.0(3) . . . 11 ?
O3 Cl1 O1 O1 45.1(12) 11 . . 11 ?
O2 Cl1 O1 O1 -96.0(4) 10_556 . . 11 ?
O2 Cl1 O1 O1 -1(2) . . . 11 ?
O1 Cl1 O1 O1 -69.8(9) 4 . . 11 ?
O1 Cl1 O1 O1 -120.3(14) 10_556 . . 11 ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        71.54
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(DPA)(170K)
_database_code_depnum_ccdc_archive 'CCDC 1028140'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Dipropylammonium)(ClO4)
_chemical_melting_point          ?
_chemical_formula_moiety         'Cl O4, C6 H16 N'
_chemical_formula_sum            'C6 H16 Cl N O4'
_chemical_formula_weight         201.65

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   8.5346(3)
_cell_length_b                   7.5928(3)
_cell_length_c                   16.1352(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1045.59(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5515
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         25.02
_reflns_number_total             996
_reflns_number_gt                840
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         991
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.28374(6) 0.2500 0.48921(3) 0.0299(2) Uani 1 2 d S . .
N1 N 0.2863(2) 0.7500 0.49116(10) 0.0236(4) Uani 1 2 d S . .
H9A H 0.3496 0.8478 0.4944 0.028 Uiso 0.50 1 calc PR . .
H9B H 0.3496 0.6522 0.4944 0.028 Uiso 0.50 1 calc PR . .
O1 O 0.3888(3) 0.3799(3) 0.4581(2) 0.0506(12) Uani 0.503(5) 1 d P A 3
C6 C 0.1449(5) 0.7500 0.7160(2) 0.0686(11) Uani 1 2 d S . .
C2 C 0.3190(3) 0.7500 0.33811(14) 0.0383(6) Uani 1 2 d S . .
H11A H 0.3868 0.6445 0.3416 0.046 Uiso 0.50 1 calc PR . .
H11B H 0.3868 0.8555 0.3416 0.046 Uiso 0.50 1 calc PR . .
C4 C 0.1770(3) 0.7500 0.56313(14) 0.0304(6) Uani 1 2 d S . .
H8A H 0.1089 0.6446 0.5599 0.037 Uiso 0.50 1 calc PR . .
H8B H 0.1089 0.8554 0.5599 0.037 Uiso 0.50 1 calc PR . .
O2 O 0.3744(3) 0.3809(3) 0.5342(2) 0.0518(13) Uani 0.501(5) 1 d P A 2
C5 C 0.2611(3) 0.7500 0.64498(15) 0.0413(6) Uani 1 2 d S . .
H7A H 0.3289 0.8555 0.6488 0.050 Uiso 0.50 1 calc PR . .
H7B H 0.3289 0.6445 0.6488 0.050 Uiso 0.50 1 calc PR . .
C3 C 0.2051(3) 0.7500 0.40951(14) 0.0314(6) Uani 1 2 d S . .
H10A H 0.1372 0.8554 0.4056 0.038 Uiso 0.50 1 calc PR . .
H10B H 0.1372 0.6446 0.4056 0.038 Uiso 0.50 1 calc PR . .
O3 O 0.1712(3) 0.3272(3) 0.54249(17) 0.0559(11) Uani 0.498(4) 1 d P . 1
C1 C 0.2324(5) 0.7500 0.2561(2) 0.0628(10) Uani 1 2 d S . .
O4 O 0.2050(3) 0.1638(4) 0.42246(17) 0.0602(11) Uani 0.499(4) 1 d P . 4
H1 H 0.196(3) 0.7500 0.765(2) 0.056(9) Uiso 1 2 d S . .
H2 H 0.164(3) 0.854(3) 0.2502(15) 0.082(8) Uiso 1 1 d . . .
H3 H 0.308(4) 0.7500 0.215(2) 0.074(11) Uiso 1 2 d S . .
H4 H 0.076(3) 0.855(3) 0.7135(16) 0.105(10) 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
Cl1 O3 1.416(2) . ?
Cl1 O3 1.416(2) 8_565 ?
Cl1 O1 1.424(2) . ?
Cl1 O1 1.424(2) 8_565 ?
Cl1 O4 1.428(2) 8_565 ?
Cl1 O4 1.428(2) . ?
Cl1 O2 1.454(3) . ?
Cl1 O2 1.454(3) 8_565 ?
N1 C3 1.489(3) . ?
N1 C4 1.490(3) . ?
N1 H9A 0.9200 . ?
N1 H9B 0.9200 . ?
C6 C5 1.516(4) . ?
C6 H1 0.90(3) . ?
C6 H4 0.99(3) . ?
C2 C3 1.507(3) . ?
C2 C1 1.516(4) . ?
C2 H11A 0.9900 . ?
C2 H11B 0.9900 . ?
C4 C5 1.503(3) . ?
C4 H8A 0.9900 . ?
C4 H8B 0.9900 . ?
C5 H7A 0.9900 . ?
C5 H7B 0.9900 . ?
C3 H10A 0.9900 . ?
C3 H10B 0.9900 . ?
O3 O3 1.173(5) 8_565 ?
C1 H2 0.99(2) . ?
C1 H3 0.93(3) . ?
O4 O4 1.309(6) 8_565 ?

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
O3 Cl1 O3 48.9(2) . 8_565 ?
O3 Cl1 O1 110.74(18) . . ?
O3 Cl1 O1 158.08(19) 8_565 . ?
O3 Cl1 O1 158.08(19) . 8_565 ?
O3 Cl1 O1 110.74(18) 8_565 8_565 ?
O1 Cl1 O1 87.6(2) . 8_565 ?
O3 Cl1 O4 87.09(16) . 8_565 ?
O3 Cl1 O4 109.19(15) 8_565 8_565 ?
O1 Cl1 O4 73.32(17) . 8_565 ?
O1 Cl1 O4 110.3(2) 8_565 8_565 ?
O3 Cl1 O4 109.19(15) . . ?
O3 Cl1 O4 87.09(17) 8_565 . ?
O1 Cl1 O4 110.3(2) . . ?
O1 Cl1 O4 73.32(17) 8_565 . ?
O4 Cl1 O4 54.5(2) 8_565 . ?
O3 Cl1 O2 76.96(16) . . ?
O3 Cl1 O2 109.93(19) 8_565 . ?
O1 Cl1 O2 50.77(16) . . ?
O1 Cl1 O2 108.34(14) 8_565 . ?
O4 Cl1 O2 108.27(18) 8_565 . ?
O4 Cl1 O2 160.08(19) . . ?
O3 Cl1 O2 109.93(19) . 8_565 ?
O3 Cl1 O2 76.96(16) 8_565 8_565 ?
O1 Cl1 O2 108.34(14) . 8_565 ?
O1 Cl1 O2 50.77(16) 8_565 8_565 ?
O4 Cl1 O2 160.08(19) 8_565 8_565 ?
O4 Cl1 O2 108.27(18) . 8_565 ?
O2 Cl1 O2 86.3(2) . 8_565 ?
C3 N1 C4 113.47(16) . . ?
C3 N1 H9A 108.9 . . ?
C4 N1 H9A 108.9 . . ?
C3 N1 H9B 108.9 . . ?
C4 N1 H9B 108.9 . . ?
H9A N1 H9B 107.7 . . ?
C5 C6 H1 109.9(19) . . ?
C5 C6 H4 110.8(16) . . ?
H1 C6 H4 108.9(18) . . ?
C3 C2 C1 110.7(2) . . ?
C3 C2 H11A 109.5 . . ?
C1 C2 H11A 109.5 . . ?
C3 C2 H11B 109.5 . . ?
C1 C2 H11B 109.5 . . ?
H11A C2 H11B 108.1 . . ?
N1 C4 C5 112.66(18) . . ?
N1 C4 H8A 109.1 . . ?
C5 C4 H8A 109.1 . . ?
N1 C4 H8B 109.1 . . ?
C5 C4 H8B 109.1 . . ?
H8A C4 H8B 107.8 . . ?
C4 C5 C6 110.6(2) . . ?
C4 C5 H7A 109.5 . . ?
C6 C5 H7A 109.5 . . ?
C4 C5 H7B 109.5 . . ?
C6 C5 H7B 109.5 . . ?
H7A C5 H7B 108.1 . . ?
N1 C3 C2 112.11(18) . . ?
N1 C3 H10A 109.2 . . ?
C2 C3 H10A 109.2 . . ?
N1 C3 H10B 109.2 . . ?
C2 C3 H10B 109.2 . . ?
H10A C3 H10B 107.9 . . ?
O3 O3 Cl1 65.53(11) 8_565 . ?
C2 C1 H2 111.8(15) . . ?
C2 C1 H3 107(2) . . ?
H2 C1 H3 109.9(18) . . ?
O4 O4 Cl1 62.73(12) 8_565 . ?

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
C3 N1 C4 C5 180.0 . . . . ?
N1 C4 C5 C6 180.000(1) . . . . ?
C4 N1 C3 C2 180.0 . . . . ?
C1 C2 C3 N1 180.0 . . . . ?
O1 Cl1 O3 O3 -170.32(18) . . . 8_565 ?
O1 Cl1 O3 O3 -24.9(4) 8_565 . . 8_565 ?
O4 Cl1 O3 O3 118.75(12) 8_565 . . 8_565 ?
O4 Cl1 O3 O3 68.00(13) . . . 8_565 ?
O2 Cl1 O3 O3 -131.75(15) . . . 8_565 ?
O2 Cl1 O3 O3 -50.64(12) 8_565 . . 8_565 ?
O3 Cl1 O4 O4 71.70(13) . . . 8_565 ?
O3 Cl1 O4 O4 116.13(12) 8_565 . . 8_565 ?
O1 Cl1 O4 O4 -50.23(11) . . . 8_565 ?
O1 Cl1 O4 O4 -131.21(15) 8_565 . . 8_565 ?
O2 Cl1 O4 O4 -33.3(4) . . . 8_565 ?
O2 Cl1 O4 O4 -168.63(16) 8_565 . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_(DPA)(ClO4)(100K)
_database_code_depnum_ccdc_archive 'CCDC 1028141'
_audit_update_record             
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (Dipropylammonium)(ClO4)
_chemical_melting_point          ?
_chemical_formula_moiety         'Cl O4, C6 H16 N'
_chemical_formula_sum            'C6 H16 Cl N O4'
_chemical_formula_weight         201.65

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P m c n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4714(8)
_cell_length_b                   16.0278(18)
_cell_length_c                   8.4874(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1016.37(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5387
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         25.01
_reflns_number_total             971
_reflns_number_gt                881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1114P)²+18.5191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         966
_refine_ls_number_parameters     98
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.1108
_refine_ls_wR_factor_ref         0.3640
_refine_ls_wR_factor_gt          0.3618
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7500 0.51139(17) 0.7096(3) 0.0198(10) Uani 1 2 d S . .
N1 N 0.2500 0.5104(5) 0.7200(11) 0.018(2) Uani 1 2 d S . .
H1A H 0.3494 0.5071 0.6564 0.022 Uiso 0.50 1 calc PR . .
H1B H 0.1506 0.5071 0.6564 0.022 Uiso 0.50 1 calc PR . .
C4 C 0.2500 0.4373(7) 0.8316(14) 0.021(3) Uani 1 2 d S . .
H4A H 0.1428 0.4403 0.9000 0.025 Uiso 0.50 1 calc PR . .
H4B H 0.3572 0.4403 0.9000 0.025 Uiso 0.50 1 calc PR . .
C2 C 0.2500 0.6652(7) 0.6841(14) 0.024(3) Uani 1 2 d S . .
H2A H 0.3573 0.6616 0.6161 0.029 Uiso 0.50 1 calc PR . .
H2B H 0.1427 0.6616 0.6161 0.029 Uiso 0.50 1 calc PR . .
O2 O 0.6243(17) 0.5486(8) 0.6019(13) 0.029(4) Uani 0.496(19) 1 d P A 2
O3 O 0.6195(17) 0.4599(8) 0.6212(14) 0.033(4) Uani 0.53(2) 1 d P A 3
O1 O 0.6476(18) 0.5750(8) 0.7898(14) 0.030(4) Uani 0.486(17) 1 d P . 1
C6 C 0.2500 0.2832(9) 0.8622(19) 0.037(4) Uani 1 2 d S . .
C5 C 0.2500 0.3553(7) 0.7444(15) 0.027(3) Uani 1 2 d S . .
H5A H 0.3573 0.3516 0.6763 0.032 Uiso 0.50 1 calc PR . .
H5B H 0.1427 0.3516 0.6763 0.032 Uiso 0.50 1 calc PR . .
C3 C 0.2500 0.5929(7) 0.8017(14) 0.025(3) Uani 1 2 d S . .
H3A H 0.3572 0.5970 0.8699 0.031 Uiso 0.50 1 calc PR . .
H3B H 0.1428 0.5970 0.8699 0.031 Uiso 0.50 1 calc PR . .
O4 O 0.6625(19) 0.4601(8) 0.8204(14) 0.032(4) Uani 0.492(19) 1 d P . 4
C1 C 0.2500 0.7473(8) 0.7714(18) 0.033(3) Uani 1 2 d S . .
H4 H 0.2500 0.237(6) 0.819(12) 0.01(3) Uiso 1 2 d S . .
H8 H 0.2500 0.7971 0.7124 0.05(5) Uiso 1 2 d SR . .
H12 H 0.193(9) 0.283(4) 0.935(8) 0.03(3) Uiso 1 1 d . . .
H1 H 0.1863 0.7502 0.8505 0.03(3) Uiso 1 1 d R . .


_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
Cl1 O4 1.410(12) . ?
Cl1 O4 1.410(12) 7_755 ?
Cl1 O2 1.440(12) 7_755 ?
Cl1 O2 1.440(12) . ?
Cl1 O1 1.446(12) 7_755 ?
Cl1 O1 1.446(12) . ?
Cl1 O3 1.482(12) . ?
Cl1 O3 1.482(12) 7_755 ?
N1 C3 1.492(13) . ?
N1 C4 1.507(14) . ?
C4 C5 1.509(16) . ?
C2 C1 1.510(17) . ?
C2 C3 1.530(16) . ?
O1 O1 1.53(3) 7_755 ?
C6 C5 1.528(18) . ?
O4 O4 1.31(3) 7_755 ?

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
O4 Cl1 O4 55.2(11) . 7_755 ?
O4 Cl1 O2 165.4(8) . 7_755 ?
O4 Cl1 O2 111.3(8) 7_755 7_755 ?
O4 Cl1 O2 111.3(8) . . ?
O4 Cl1 O2 165.4(8) 7_755 . ?
O2 Cl1 O2 81.4(10) 7_755 . ?
O4 Cl1 O1 110.0(7) . 7_755 ?
O4 Cl1 O1 81.5(7) 7_755 7_755 ?
O2 Cl1 O1 70.2(7) 7_755 7_755 ?
O2 Cl1 O1 110.6(7) . 7_755 ?
O4 Cl1 O1 81.5(7) . . ?
O4 Cl1 O1 110.0(7) 7_755 . ?
O2 Cl1 O1 110.6(7) 7_755 . ?
O2 Cl1 O1 70.2(7) . . ?
O1 Cl1 O1 63.9(11) 7_755 . ?
O4 Cl1 O3 73.0(7) . . ?
O4 Cl1 O3 108.5(7) 7_755 . ?
O2 Cl1 O3 109.8(7) 7_755 . ?
O2 Cl1 O3 58.7(7) . . ?
O1 Cl1 O3 168.6(7) 7_755 . ?
O1 Cl1 O3 106.5(7) . . ?
O4 Cl1 O3 108.5(7) . 7_755 ?
O4 Cl1 O3 73.0(7) 7_755 7_755 ?
O2 Cl1 O3 58.7(7) 7_755 7_755 ?
O2 Cl1 O3 109.8(7) . 7_755 ?
O1 Cl1 O3 106.5(7) 7_755 7_755 ?
O1 Cl1 O3 168.6(7) . 7_755 ?
O3 Cl1 O3 82.3(10) . 7_755 ?
C3 N1 C4 113.4(9) . . ?
N1 C4 C5 111.7(9) . . ?
C1 C2 C3 109.9(10) . . ?
Cl1 O1 O1 58.0(5) . 7_755 ?
C4 C5 C6 109.8(11) . . ?
N1 C3 C2 111.6(9) . . ?
O4 O4 Cl1 62.4(6) 7_755 . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.045
_refine_diff_density_min         -1.598
_refine_diff_density_rms         0.204
