#------------------------------------------------------------------------------
#$Date: 2015-06-07 01:07:56 +0300 (Sun, 07 Jun 2015) $
#$Revision: 138536 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/03/7220316.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_7220316
loop_
_publ_author_name
'Wang, Wen-Xiang'
'Huang, Yao'
_publ_section_title
;
 High temperature phase transitions in N,N-diisopropylpropan-1-ammonium
 perchlorate
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3783
_journal_paper_doi               10.1039/C4CE02562H
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C9 H22 N Cl O4'
_chemical_formula_sum            'C9 H22 Cl N O4'
_chemical_formula_weight         243.73
_chemical_melting_point          460.2(3)
_chemical_name_systematic
'N, N-diisopropylpropan-1-ammonium perchlorate'
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-04-14 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                   16.126(3)
_cell_length_b                   8.7468(17)
_cell_length_c                   9.3691(19)
_cell_measurement_reflns_used    6488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.12
_cell_volume                     1321.5(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13071
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_preparation       'ferroelectric phase transition'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0526P)²+0.0733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                2045
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce02562h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '460-460.5' was changed to '460.2(3)'
- the average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7220316.cif.
;
_cod_original_cell_volume        1321.5(5)
_cod_database_code               7220316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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
N1 N 0.84565(13) 0.5994(2) 0.2728(2) 0.0468(6) Uani 1 1 d .
H1D H 0.8474 0.6226 0.1782 0.056 Uiso 1 1 calc R
C7 C 0.86728(19) 0.7447(3) 0.3467(5) 0.0647(7) Uani 1 1 d .
H7A H 0.8202 0.8133 0.3398 0.078 Uiso 1 1 calc R
H7B H 0.8758 0.7225 0.4471 0.078 Uiso 1 1 calc R
C5 C 0.7253(2) 0.5710(5) 0.4498(4) 0.0817(11) Uani 1 1 d .
H5A H 0.7151 0.6780 0.4641 0.123 Uiso 1 1 calc R
H5B H 0.7664 0.5365 0.5167 0.123 Uiso 1 1 calc R
H5C H 0.6748 0.5149 0.4641 0.123 Uiso 1 1 calc R
C9 C 0.9603(2) 0.9684(4) 0.3741(5) 0.0953(13) Uani 1 1 d .
H9A H 0.9755 0.9424 0.4702 0.143 Uiso 1 1 calc R
H9B H 0.9122 1.0330 0.3753 0.143 Uiso 1 1 calc R
H9C H 1.0055 1.0213 0.3291 0.143 Uiso 1 1 calc R
C2 C 0.91219(18) 0.4756(3) 0.2929(3) 0.0564(7) Uani 1 1 d .
H2 H 0.9661 0.5254 0.2799 0.068 Uiso 1 1 calc R
C3 C 0.9122(3) 0.4076(4) 0.4391(3) 0.0717(10) Uani 1 1 d .
H3A H 0.9588 0.3401 0.4490 0.108 Uiso 1 1 calc R
H3B H 0.8618 0.3513 0.4535 0.108 Uiso 1 1 calc R
H3C H 0.9160 0.4878 0.5088 0.108 Uiso 1 1 calc R
C6 C 0.75629(16) 0.5450(4) 0.2993(3) 0.0593(8) Uani 1 1 d .
H6 H 0.7547 0.4347 0.2812 0.071 Uiso 1 1 calc R
C1 C 0.9047(2) 0.3570(4) 0.1786(3) 0.0698(9) Uani 1 1 d .
H1A H 0.8559 0.2967 0.1948 0.105 Uiso 1 1 calc R
H1B H 0.9527 0.2920 0.1804 0.105 Uiso 1 1 calc R
H1C H 0.9008 0.4061 0.0872 0.105 Uiso 1 1 calc R
C8 C 0.9414(2) 0.8255(4) 0.2925(4) 0.0809(11) Uani 1 1 d .
H8A H 0.9328 0.8514 0.1930 0.097 Uiso 1 1 calc R
H8B H 0.9888 0.7574 0.2979 0.097 Uiso 1 1 calc R
C4 C 0.6992(2) 0.6206(5) 0.1926(4) 0.0849(12) Uani 1 1 d .
H4A H 0.7022 0.7296 0.2035 0.127 Uiso 1 1 calc R
H4B H 0.6433 0.5872 0.2089 0.127 Uiso 1 1 calc R
H4C H 0.7158 0.5931 0.0976 0.127 Uiso 1 1 calc R
Cl1 Cl 0.84413(4) 0.62881(8) -0.16659(9) 0.0553(2) Uani 1 1 d .
O2 O 0.8728(2) 0.7279(3) -0.2756(3) 0.0974(9) Uani 1 1 d .
O4 O 0.75746(13) 0.6179(3) -0.1733(4) 0.1039(8) Uani 1 1 d .
O3 O 0.86823(15) 0.6898(3) -0.0309(2) 0.0760(7) Uani 1 1 d .
O1 O 0.88031(16) 0.4838(3) -0.1855(3) 0.0982(8) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0502(13) 0.0494(13) 0.0409(12) 0.0014(10) 0.0001(10) 0.0017(10)
C7 0.0769(18) 0.0578(16) 0.0592(18) -0.0090(17) -0.0002(19) -0.0063(14)
C5 0.064(2) 0.115(3) 0.065(2) -0.001(2) 0.0182(16) -0.013(2)
C9 0.087(2) 0.068(2) 0.131(4) -0.017(2) 0.004(2) -0.017(2)
C2 0.0530(15) 0.0572(16) 0.0589(19) 0.0014(14) -0.0019(13) 0.0068(13)
C3 0.089(2) 0.072(2) 0.054(2) 0.0087(16) -0.0090(17) 0.0153(19)
C6 0.0495(15) 0.0732(19) 0.055(2) -0.0035(14) 0.0042(13) -0.0041(13)
C1 0.083(2) 0.066(2) 0.060(2) -0.0024(17) 0.0032(18) 0.0126(18)
C8 0.080(2) 0.073(2) 0.090(3) -0.0063(18) 0.0150(18) -0.0202(18)
C4 0.057(2) 0.129(4) 0.069(2) 0.015(2) -0.0026(18) 0.012(2)
Cl1 0.0564(3) 0.0680(4) 0.0415(3) 0.0004(4) 0.0003(4) 0.0067(3)
O2 0.133(2) 0.110(2) 0.0491(15) 0.0147(14) 0.0072(15) -0.0151(18)
O4 0.0587(12) 0.165(2) 0.0883(16) -0.0085(19) -0.0029(18) 0.0023(13)
O3 0.0963(18) 0.0874(17) 0.0442(13) -0.0028(12) -0.0068(11) -0.0105(14)
O1 0.1142(17) 0.0837(15) 0.097(2) -0.0213(16) -0.0036(18) 0.0282(14)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 114.1(2)
C7 N1 C2 112.4(2)
C6 N1 C2 114.6(2)
C7 N1 H1D 104.8
C6 N1 H1D 104.8
C2 N1 H1D 104.8
C8 C7 N1 116.0(3)
C8 C7 H7A 108.3
N1 C7 H7A 108.3
C8 C7 H7B 108.3
N1 C7 H7B 108.3
H7A C7 H7B 107.4
C6 C5 H5A 109.5
C6 C5 H5B 109.5
H5A C5 H5B 109.5
C6 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 C2 C3 112.4(3)
C1 C2 N1 110.2(2)
C3 C2 N1 113.1(3)
C1 C2 H2 106.9
C3 C2 H2 106.9
N1 C2 H2 106.9
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C5 C6 C4 110.5(3)
C5 C6 N1 114.4(2)
C4 C6 N1 109.2(3)
C5 C6 H6 107.5
C4 C6 H6 107.5
N1 C6 H6 107.5
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C8 C9 112.9(3)
C7 C8 H8A 109.0
C9 C8 H8A 109.0
C7 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
C6 C4 H4A 109.5
C6 C4 H4B 109.5
H4A C4 H4B 109.5
C6 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O4 Cl1 O1 110.26(17)
O4 Cl1 O2 109.57(19)
O1 Cl1 O2 109.0(2)
O4 Cl1 O3 109.59(18)
O1 Cl1 O3 109.55(17)
O2 Cl1 O3 108.87(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.489(4)
N1 C6 1.538(3)
N1 C2 1.536(4)
N1 H1D 0.9100
C7 C8 1.479(4)
C7 H7A 0.9700
C7 H7B 0.9700
C5 C6 1.513(4)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C9 C8 1.496(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C2 C1 1.495(4)
C2 C3 1.494(4)
C2 H2 0.9800
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
C6 C4 1.512(4)
C6 H6 0.9800
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C8 H8A 0.9700
C8 H8B 0.9700
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
Cl1 O4 1.402(2)
Cl1 O1 1.407(2)
Cl1 O2 1.417(3)
Cl1 O3 1.432(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
N1 H1D O3 0.91 2.07 2.975(3) 171.5
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
C6 N1 C7 C8 -162.4(3)
C2 N1 C7 C8 64.9(4)
C7 N1 C2 C1 -159.4(3)
C6 N1 C2 C1 68.1(3)
C7 N1 C2 C3 73.8(3)
C6 N1 C2 C3 -58.6(3)
C7 N1 C6 C5 -38.2(4)
C2 N1 C6 C5 93.5(3)
C7 N1 C6 C4 86.2(3)
C2 N1 C6 C4 -142.2(3)
N1 C7 C8 C9 -178.7(3)
