#------------------------------------------------------------------------------
#$Date: 2019-11-03 10:57:09 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/80/4128068.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_4128068
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         'C8 H14 N, Cl O4'
_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   geom
_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                   12.3345(6)
_cell_length_b                   8.4335(4)
_cell_length_c                   9.7578(5)
_cell_measurement_reflns_used    2498
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.3540
_cell_measurement_theta_min      2.6660
_cell_volume                     1015.04(9)
_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      93(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5659
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.662
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.919
_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    1.464
_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         0.366
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²+0.7208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                827
_reflns_number_total             964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b13223_si_007.cif
_cod_data_source_block           Pnma
_cod_database_code               4128068
_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   0.921
_shelx_estimated_absorpt_t_max   0.924
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
Cl1 Cl 0.04824(5) 0.2500 0.71426(7) 0.0240(3) Uani 1 2 d S T P
C1 C 0.26233(18) 0.1042(2) 0.0176(2) 0.0273(5) Uani 1 1 d . . .
H1A H 0.3085 0.0083 0.0223 0.033 Uiso 1 1 calc R U .
H1B H 0.2241 0.1041 -0.0716 0.033 Uiso 1 1 calc R U .
C2 C 0.17953(18) 0.1020(3) 0.1350(2) 0.0305(6) Uani 1 1 d . . .
H2A H 0.1893 0.0051 0.1909 0.037 Uiso 1 1 calc R U .
H2B H 0.1051 0.1013 0.0971 0.037 Uiso 1 1 calc R U .
C3 C 0.1959(2) 0.2500 0.2248(3) 0.0265(7) Uani 1 2 d S T P
H3 H 0.1434 0.2500 0.3028 0.032 Uiso 1 2 calc R U P
C4 C 0.3107(2) 0.2500 0.2775(3) 0.0223(7) Uani 1 2 d S T P
C5 C 0.3923(2) 0.2500 0.1625(3) 0.0233(7) Uani 1 2 d S T P
H5A H 0.4389 0.3452 0.1685 0.028 Uiso 0.5 1 calc R U P
H5B H 0.4389 0.1548 0.1685 0.028 Uiso 0.5 1 calc R U P
C6 C 0.3399(3) 0.2500 0.4073(3) 0.0279(7) Uani 1 2 d S T P
H6A H 0.2863 0.2500 0.4772 0.033 Uiso 1 2 calc R U P
H6B H 0.4146 0.2500 0.4310 0.033 Uiso 1 2 calc R U P
N1 N 0.33132(19) 0.2500 0.0297(2) 0.0227(6) Uani 1 2 d S T P
H1 H 0.3850 0.2500 -0.0472 0.027 Uiso 1 2 calc R U P
O1 O -0.00203(15) 0.11348(19) 0.6534(2) 0.0495(6) Uani 1 1 d . . .
O2 O 0.16172(19) 0.2500 0.6876(2) 0.0400(6) Uani 1 2 d S T P
O3 O 0.0316(2) 0.2500 0.8579(3) 0.0695(11) Uani 1 2 d S T 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 108.84(16) . .
O3 Cl1 O1 110.27(11) . .
O2 Cl1 O1 110.43(10) . .
O3 Cl1 O1 110.27(11) . 7_565
O2 Cl1 O1 110.42(10) . 7_565
O1 Cl1 O1 106.59(14) . 7_565
N1 C1 C2 109.19(17) . .
C1 C2 C3 109.15(18) . .
C4 C3 C2 108.57(16) . .
C4 C3 C2 108.57(16) . 7_565
C2 C3 C2 108.4(2) . 7_565
C6 C4 C3 125.9(3) . .
C6 C4 C5 122.2(3) . .
C3 C4 C5 111.9(2) . .
N1 C5 C4 108.0(2) . .
C5 N1 C1 110.62(14) . 7_565
C5 N1 C1 110.62(14) . .
C1 N1 C1 110.1(2) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 O3 1.417(3) .
Cl1 O2 1.424(2) .
Cl1 O1 1.4361(17) .
Cl1 O1 1.4361(17) 7_565
C1 N1 1.500(2) .
C1 C2 1.534(3) .
C2 C3 1.538(3) .
C3 C4 1.506(4) .
C3 C2 1.538(3) 7_565
C4 C6 1.316(4) .
C4 C5 1.508(4) .
C5 N1 1.498(4) .
N1 C1 1.500(2) 7_565
