#------------------------------------------------------------------------------
#$Date: 2016-11-06 03:49:29 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187930 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/52/4125279.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_4125279
loop_
_publ_author_name
'Ye, Heng-Yun'
'Ge, Jia-Zhen'
'Tang, Yuan-Yuan'
'Li, Peng-Fei'
'Zhang, Yi'
'You, Yu-Meng'
'Xiong, Ren-Gen'
_publ_section_title
;
 Molecular Ferroelectric with Most Equivalent Polarization Directions
 Induced by the Plastic Phase Transition.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13175
_journal_paper_doi               10.1021/jacs.6b08817
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C8 H20 Cl N O4'
_chemical_formula_weight         229.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.009(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.518(8)
_cell_length_b                   7.417(4)
_cell_length_c                   13.997(9)
_cell_measurement_reflns_used    1568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      3.2121
_cell_volume                     1177.7(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku saturn 724'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6186
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         3.212
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0464P)²+1.5143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1198
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2418
_reflns_number_total             2673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08817_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125279.cif.
;
_cod_original_cell_volume        1177.7(13)
_cod_database_code               4125279
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 0.00000(9) -0.87269(12) 0.00000(9) 0.0287(2) Uani 1 1 d . .
N1 N -0.6300(3) -0.8795(5) -0.2512(2) 0.0246(7) Uani 1 1 d . .
C1 C -0.5061(4) -0.8777(6) -0.1633(3) 0.0317(10) Uani 1 1 d . .
H1A H -0.5033 -0.7887 -0.1096 0.038 Uiso 1 1 calc R U
H1B H -0.4894 -0.9977 -0.1292 0.038 Uiso 1 1 calc R U
C2 C -0.6403(4) -1.0069(6) -0.3393(4) 0.0357(10) Uani 1 1 d . .
H2A H -0.5932 -0.9575 -0.3750 0.043 Uiso 1 1 calc R U
H2B H -0.7237 -1.0095 -0.3918 0.043 Uiso 1 1 calc R U
C3 C -0.7134(4) -0.9422(7) -0.2056(3) 0.0325(10) Uani 1 1 d . .
H3A H -0.7933 -0.9529 -0.2636 0.039 Uiso 1 1 calc R U
H3B H -0.6888 -1.0640 -0.1753 0.039 Uiso 1 1 calc R U
C4 C -0.6598(4) -0.6907(6) -0.2959(3) 0.0300(9) Uani 1 1 d . .
H4A H -0.6464 -0.6061 -0.2373 0.036 Uiso 1 1 calc R U
H4B H -0.6046 -0.6574 -0.3270 0.036 Uiso 1 1 calc R U
C5 C -0.4097(5) -0.8326(9) -0.1977(5) 0.0523(16) Uani 1 1 d . .
H5A H -0.3331 -0.8344 -0.1363 0.078 Uiso 1 1 calc R U
H5B H -0.4098 -0.9218 -0.2494 0.078 Uiso 1 1 calc R U
H5C H -0.4237 -0.7123 -0.2297 0.078 Uiso 1 1 calc R U
C6 C -0.6006(7) -1.1991(8) -0.3059(6) 0.0594(17) Uani 1 1 d . .
H6A H -0.6105 -1.2707 -0.3680 0.089 Uiso 1 1 calc R U
H6B H -0.5173 -1.1993 -0.2557 0.089 Uiso 1 1 calc R U
H6C H -0.6482 -1.2515 -0.2725 0.089 Uiso 1 1 calc R U
C7 C -0.7201(6) -0.8215(10) -0.1215(5) 0.0575(18) Uani 1 1 d . .
H7A H -0.7760 -0.8723 -0.0966 0.086 Uiso 1 1 calc R U
H7B H -0.6419 -0.8126 -0.0625 0.086 Uiso 1 1 calc R U
H7C H -0.7466 -0.7012 -0.1509 0.086 Uiso 1 1 calc R U
C8 C -0.7841(5) -0.6661(9) -0.3787(5) 0.0449(15) Uani 1 1 d . .
H8A H -0.7955 -0.5407 -0.4031 0.067 Uiso 1 1 calc R U
H8B H -0.7979 -0.7465 -0.4383 0.067 Uiso 1 1 calc R U
H8C H -0.8398 -0.6951 -0.3484 0.067 Uiso 1 1 calc R U
O4 O 0.0104(4) -0.9903(6) 0.0835(3) 0.0585(12) Uani 1 1 d . .
O3 O 0.0409(5) -0.9575(8) -0.0675(4) 0.0890(19) Uani 1 1 d . .
O2 O -0.1173(5) -0.8303(13) -0.0585(6) 0.143(4) Uani 1 1 d . .
O1 O 0.0623(9) -0.7188(9) 0.0373(5) 0.153(4) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 Cl1 O2 109.3(7)
O1 Cl1 O3 108.8(5)
O2 Cl1 O3 107.7(5)
O1 Cl1 O4 111.3(4)
O2 Cl1 O4 109.4(3)
O3 Cl1 O4 110.3(3)
C3 N1 C4 111.5(3)
C3 N1 C2 108.5(3)
C4 N1 C2 108.6(3)
C3 N1 C1 108.2(3)
C4 N1 C1 108.4(3)
C2 N1 C1 111.8(3)
C5 C1 N1 115.0(4)
N1 C2 C6 115.5(4)
C7 C3 N1 115.1(4)
C8 C4 N1 115.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 O1 1.356(5)
Cl1 O2 1.382(5)
Cl1 O3 1.399(5)
Cl1 O4 1.420(4)
N1 C3 1.509(5)
N1 C4 1.515(5)
N1 C2 1.516(5)
N1 C1 1.519(5)
C1 C5 1.514(7)
C2 C6 1.517(8)
C3 C7 1.508(8)
C4 C8 1.508(7)
