#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:47:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180276 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/62/7116261.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_7116261
loop_
_publ_author_name
'Ji, Chengmin'
'Sun, Zhihua'
'Zhang, Shuquan'
'Zhao, Sangen'
'Chen, Tianliang'
'Tang, Yuanyuan'
'Luo, Junhua'
_publ_section_title
;
 A host-guest inclusion compound for reversible switching of quadratic
 nonlinear optical properties.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2298
_journal_page_last               2300
_journal_paper_doi               10.1039/c4cc08711a
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'Cl O4, C6 H16 N'
_chemical_formula_sum            'C6 H16 Cl N O4'
_chemical_formula_weight         201.65
_chemical_name_common            (Dipropylammonium)(ClO4)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-08 deposited with the CCDC.
2014-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5346(3)
_cell_length_b                   7.5928(3)
_cell_length_c                   16.1352(6)
_cell_measurement_temperature    170(2)
_cell_volume                     1045.59(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5515
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0346
_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)+(0.0463P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                840
_reflns_number_total             996
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08711a3.cif
_cod_data_source_block           (DPA)(170K)
_cod_depositor_comments
'Adding full bibliography for 7116258--7116262.cif.'
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7116261
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'
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 . . .
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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_4
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
