#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:20:05 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180422 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/91/7209116.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_7209116
loop_
_publ_author_name
'Piecha, Anna'
'Gągor, Anna'
'Jakubas, Ryszard'
'Szklarz, Przemysław'
_publ_section_title
;
 Room-temperature ferroelectricity in diisopropylammonium bromide
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              940
_journal_paper_doi               10.1039/c2ce26580j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C6 H16 Br N'
_chemical_formula_weight         182.11
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.379(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.9465(14)
_cell_length_b                   8.1567(14)
_cell_length_c                   7.9743(14)
_cell_measurement_reflns_used    4620
_cell_measurement_temperature    435(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.85
_cell_volume                     463.05(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      435(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4620
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    4.362
_exptl_absorpt_correction_T_max  0.495
_exptl_absorpt_correction_T_min  0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         944
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                734
_reflns_number_total             944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26580j.txt
_cod_data_source_block           p21m-1
_cod_original_cell_volume        463.05(14)
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               7209116
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'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
Br1 Br 0.35574(3) 0.2500 0.63203(3) 0.08100(8) Uani 1 2 d S . .
C4 C 0.6150(4) 0.2500 0.2952(4) 0.0850(9) Uani 1 2 d SD . 1
C1 C 0.8686(3) 0.3155(3) 0.6332(3) 0.0801(9) Uiso 0.50 1 d PD . 1
C2 C 0.8894(6) 0.4354(3) 0.7831(4) 0.1150(14) Uiso 0.50 1 d PD . 1
H2A H 0.7734 0.4424 0.7927 0.173 Uiso 0.50 1 calc PR . 1
H2B H 0.9207 0.5412 0.7524 0.173 Uiso 0.50 1 calc PR . 1
H2C H 0.9875 0.3994 0.9005 0.173 Uiso 0.50 1 calc PR . 1
C3 C 0.8794(5) 0.1420(3) 0.6967(5) 0.1068(13) Uiso 0.50 1 d PD . 1
H3A H 1.0082 0.1071 0.7547 0.160 Uiso 0.50 1 calc PR . 1
H3B H 0.8086 0.0732 0.5909 0.160 Uiso 0.50 1 calc PR . 1
H3C H 0.8285 0.1341 0.7853 0.160 Uiso 0.50 1 calc PR . 1
N1 N 0.6725(3) 0.3452(3) 0.4754(3) 0.0634(7) Uani 0.50 1 d P . 1
H1A H 0.5899(19) 0.3234(6) 0.5191(11) 0.076 Uiso 0.50 1 calc PR . 1
H1B H 0.6625(4) 0.451(2) 0.4475(7) 0.076 Uiso 0.50 1 calc PR . 1
C6 C 0.7513(4) 0.2500 0.2120(4) 0.1380(16) Uani 1 2 d S . 1
H6A H 0.8239 0.1514 0.2473 0.207 Uiso 0.50 1 d P A 1
H6B H 0.8317 0.3434 0.2566 0.207 Uiso 0.50 1 d P B 1
H6C H 0.6821 0.2500 0.0779 0.207 Uiso 1 2 d S C 1
C5 C 0.4197(5) 0.2988(6) 0.1616(4) 0.107(2) Uani 0.50 1 d P . 1
H5A H 0.3723 0.2246 0.0573 0.161 Uiso 0.50 1 calc PR . 1
H5B H 0.4207 0.4082 0.1177 0.161 Uiso 0.50 1 calc PR . 1
H5C H 0.3406 0.2949 0.2240 0.161 Uiso 0.50 1 calc PR . 1
H1 H 0.9567(4) 0.311(4) 0.5910(6) 0.129 Uiso 0.50 1 d PD D 1
H4 H 0.623(3) 0.1473(4) 0.3391(11) 0.129 Uiso 0.50 1 d PD E 1
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
Br1 0.08761(10) 0.07064(14) 0.09980(12) 0.000 0.05523(8) 0.000
C4 0.1013(14) 0.0701(14) 0.0838(12) 0.000 0.0413(10) 0.000
N1 0.0584(9) 0.0667(13) 0.0656(11) -0.0022(11) 0.0278(7) -0.0029(10)
C6 0.1217(15) 0.200(4) 0.1256(15) 0.000 0.0851(10) 0.000
C5 0.0884(17) 0.146(6) 0.0760(17) -0.017(2) 0.0255(13) -0.022(2)
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'
Br Br -0.2901 2.4595 '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
C6 C4 C5 114.2(3) . 4_565
C6 C4 C5 114.2(3) . .
C6 C4 N1 116.56(19) . .
C5 C4 N1 126.4(3) 4_565 .
C5 C4 N1 108.6(2) . .
C6 C4 N1 116.56(19) . 4_565
C5 C4 N1 108.6(2) 4_565 4_565
C5 C4 N1 126.4(3) . 4_565
C6 C4 H4 103.6(14) . .
C5 C4 H4 84.1(11) 4_565 .
C5 C4 H4 113.2(13) . .
N1 C4 H4 99.7(6) . .
C2 C1 C3 112.3(2) . .
C2 C1 N1 105.4(2) . .
C3 C1 N1 108.3(2) . .
C2 C1 H1 119.9(17) . .
C3 C1 H1 98(2) . .
N1 C1 H1 112.1(5) . .
C4 N1 C1 117.9(2) . .
C4 C6 H6A 109.2 . .
C4 C6 H6B 109.2 . .
H6A C6 H6B 110.2 . .
C4 C6 H6C 108.9 . .
H6A C6 H6C 107.5 . .
H6B C6 H6C 111.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C6 1.501(5) .
C4 C5 1.494(4) 4_565
C4 C5 1.494(4) .
C4 N1 1.514(3) .
C4 N1 1.514(3) 4_565
C4 H4 0.900(5) .
C1 C2 1.495(4) .
C1 C3 1.492(3) .
C1 N1 1.526(3) .
C1 H1 0.903(5) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
N1 H1A 0.8869 .
N1 H1B 0.8869 .
C6 H6A 0.9558 .
C6 H6B 0.9555 .
C6 H6C 0.9610 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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 H1A Br1 0.89 2.47 3.360(3) 177.2 .
N1 H1B Br1 0.89 2.51 3.393(3) 178.1 3_666
