#------------------------------------------------------------------------------
#$Date: 2019-11-03 10:59:50 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/80/4128075.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_4128075
loop_
_publ_author_name
'Yang, Chen-Kai'
'Chen, Wang-Nan'
'Ding, Yan-Ting'
'Wang, Jing'
'Rao, Yin'
'Liao, Wei-Qiang'
'Xie, Yongfa'
'Zou, Wennan'
'Xiong, Ren-Gen'
_publ_section_title
;
 Directional Intermolecular Interactions for Precise Molecular Design of a
 High- Tc Multiaxial Molecular Ferroelectric.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1781
_journal_page_last               1787
_journal_paper_doi               10.1021/jacs.8b13223
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'Cl O4, C8 H14 N'
_chemical_formula_sum            'C8 H14 Cl N O4'
_chemical_formula_weight         223.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6355(12)
_cell_length_b                   8.6920(7)
_cell_length_c                   9.6224(7)
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.0130
_cell_measurement_theta_min      3.1390
_cell_volume                     1056.81(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5790
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_refine_diff_density_max         1.189
_refine_diff_density_min         -1.407
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1203
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1270
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3422
_refine_ls_wR_factor_ref         0.3541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                904
_reflns_number_total             1232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b13223_si_008.cif
_cod_data_source_block           Pnma
_cod_database_code               4128075
_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.
;
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.927
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.04113(15) 0.2500 0.71293(19) 0.0613(8) Uani 0.5 2 d DS TU P A 1
O1 O -0.0071(16) 0.116(3) 0.645(2) 0.226(9) Uani 0.5 1 d D U P A 1
O2 O 0.1536(10) 0.2500 0.7010(14) 0.092(3) Uani 0.5 2 d DS TU P A 1
O3 O 0.0288(15) 0.2500 0.8564(17) 0.142(6) Uani 0.5 2 d DS TU P A 1
Cl1' Cl 0.04113(15) 0.2500 0.71293(19) 0.0613(8) Uani 0.5 2 d DS TU P B 2
O1' O 0.0565(11) 0.2500 0.5715(17) 0.226(9) Uani 1 2 d DS TU P B 2
O2' O 0.0619(14) 0.121(3) 0.802(2) 0.092(3) Uani 0.25 1 d D U P B 2
O3' O -0.0752(13) 0.2500 0.7293(18) 0.142(6) Uani 0.5 2 d DS TU P B 2
N1 N 0.3312(5) 0.2500 0.0448(6) 0.0530(14) Uani 1 2 d S T P . .
H1 H 0.3832 0.2500 -0.0308 0.064 Uiso 1 2 d R U P . .
C1 C 0.2651(5) 0.1094(6) 0.0307(6) 0.0679(16) Uani 1 1 d . . . . .
H1A H 0.2316 0.1060 -0.0599 0.081 Uiso 1 1 d R U . . .
H1B H 0.3097 0.0192 0.0400 0.081 Uiso 1 1 d R U . . .
C2 C 0.1840(5) 0.1072(9) 0.1445(7) 0.089(2) Uani 1 1 d . . . . .
H2A H 0.1902 0.0143 0.1997 0.107 Uiso 1 1 d R U . . .
H2B H 0.1142 0.1088 0.1026 0.107 Uiso 1 1 d R U . . .
C3 C 0.1978(6) 0.2500 0.2362(8) 0.075(3) Uani 1 2 d S T P . .
H3 H 0.1455 0.2500 0.3113 0.090 Uiso 1 2 d R U P . .
C4 C 0.3076(6) 0.2500 0.2941(7) 0.0495(15) Uani 1 2 d S T P . .
C5 C 0.3878(5) 0.2500 0.1827(8) 0.0562(17) Uani 1 2 d S T P . .
H5A H 0.4323 0.3406 0.1901 0.067 Uiso 0.5 1 d R U P . .
H5B H 0.4323 0.1594 0.1901 0.067 Uiso 0.5 1 d R U P . .
C6 C 0.3311(8) 0.2500 0.4275(8) 0.072(2) Uani 1 2 d S T P . .
H6A H 0.2786 0.2500 0.4952 0.086 Uiso 1 2 d R U P . .
H6B H 0.4021 0.2500 0.4533 0.086 Uiso 1 2 d R U P . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 Cl1 O2 101.1(10) . .
O3 Cl1 O1 113.5(10) . .
O2 Cl1 O1 112.2(10) . .
O3 Cl1 O1 113.5(10) . 7_565
O2 Cl1 O1 112.2(11) . 7_565
O1 Cl1 O1 104.7(19) . 7_565
O1' Cl1' O2' 124.5(9) . .
O1' Cl1' O2' 124.5(9) . 7_565
O2' Cl1' O2' 102.6(18) . 7_565
O1' Cl1' O3' 104.2(9) . .
O2' Cl1' O3' 96.8(8) . .
O2' Cl1' O3' 96.8(8) 7_565 .
C1 N1 C1 110.6(6) . 7_565
C1 N1 C5 110.3(4) . .
C1 N1 C5 110.3(4) 7_565 .
N1 C1 C2 109.2(5) . .
C1 C2 C3 109.3(5) . .
C4 C3 C2 108.7(5) . .
C4 C3 C2 108.7(5) . 7_565
C2 C3 C2 108.2(7) . 7_565
C6 C4 C5 123.6(8) . .
C6 C4 C3 124.9(7) . .
C5 C4 C3 111.5(6) . .
C4 C5 N1 108.3(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 O3 1.390(16) .
Cl1 O2 1.426(13) .
Cl1 O1 1.47(2) .
Cl1 O1 1.47(2) 7_565
Cl1' O1' 1.375(16) .
Cl1' O2' 1.434(19) .
Cl1' O2' 1.434(19) 7_565
Cl1' O3' 1.479(17) .
N1 C1 1.486(6) .
N1 C1 1.486(6) 7_565
N1 C5 1.507(9) .
C1 C2 1.500(8) .
C2 C3 1.533(8) .
C3 C4 1.495(10) .
C3 C2 1.533(8) 7_565
C4 C6 1.317(10) .
C4 C5 1.475(10) .
