#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:17:31 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/29/7232971.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_7232971
loop_
_publ_author_name
'Jin, Tong'
'Zhang, Wen'
_publ_section_title
;
 Geometric H/D isotope effect in a series of organic salts involving short
 O--H⋯O hydrogen bonds between carboxyl and carboxylate groups
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              4238
_journal_paper_doi               10.1039/C9CE00734B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C8 D F4 O4, C4 H9 D3 N O'
_chemical_formula_sum            'C12 H9 D4 F4 N O5'
_chemical_formula_weight         331.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-13 deposited with the CCDC.    2019-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.26(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6156(18)
_cell_length_b                   17.699(3)
_cell_length_c                   9.019(2)
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.598
_cell_measurement_theta_min      2.258
_cell_volume                     1439.9(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.598
_diffrn_reflns_theta_min         2.258
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0544
_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)+(0.0387P)²+0.3518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00734b2.cif
_cod_data_source_block           10-D
_cod_depositor_comments
'Adding full bibliography for 7232953--7232976.cif.'
_cod_original_cell_volume        1440.0(5)
_cod_database_code               7232971
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.0753(2) 0.69596(15) 0.1140(3) 0.0454(6) Uani 1 1 d . .
C2 C 0.2152(2) 0.70781(13) 0.0740(3) 0.0389(5) Uani 1 1 d . .
C3 C 0.2900(2) 0.64760(14) 0.0377(3) 0.0462(6) Uani 1 1 d . .
C4 C 0.4169(2) 0.65836(14) 0.0020(3) 0.0432(6) Uani 1 1 d . .
C5 C 0.4752(2) 0.72950(13) 0.0015(2) 0.0384(5) Uani 1 1 d . .
C6 C 0.4007(2) 0.78920(13) 0.0375(3) 0.0435(6) Uani 1 1 d . .
C7 C 0.2743(2) 0.77861(13) 0.0730(3) 0.0418(6) Uani 1 1 d . .
C8 C 0.6176(2) 0.74235(14) -0.0310(3) 0.0429(6) Uani 1 1 d . .
C9 C 0.8587(5) 0.5772(2) 0.7837(4) 0.1229(15) Uani 1 1 d . .
H9A H 0.7673 0.5807 0.8041 0.184 Uiso 1 1 calc R U
H9B H 0.9192 0.6204 0.8278 0.184 Uiso 1 1 calc R U
H9C H 0.9103 0.5320 0.8313 0.184 Uiso 1 1 calc R U
C10 C 0.7400(3) 0.51396(17) 0.5451(3) 0.0712(8) Uani 1 1 d . .
H10A H 0.6585 0.5076 0.5840 0.085 Uiso 1 1 calc R U
H10B H 0.7982 0.4679 0.5664 0.085 Uiso 1 1 calc R U
C11 C 0.6810(3) 0.52856(16) 0.3718(3) 0.0633(7) Uani 1 1 d . .
H11A H 0.6100 0.5696 0.3511 0.076 Uiso 1 1 calc R U
H11B H 0.6283 0.4839 0.3189 0.076 Uiso 1 1 calc R U
C12 C 0.7965(3) 0.54832(15) 0.3011(3) 0.0605(7) Uani 1 1 d . .
H12A H 0.8742 0.5104 0.3316 0.073 Uiso 1 1 calc R U
H12B H 0.7519 0.5477 0.1868 0.073 Uiso 1 1 calc R U
F1 F 0.21008(14) 0.83957(8) 0.11159(19) 0.0642(4) Uani 1 1 d . .
F2 F 0.45540(16) 0.85964(8) 0.0442(2) 0.0731(5) Uani 1 1 d . .
F3 F 0.23843(15) 0.57692(8) 0.0337(2) 0.0759(5) Uani 1 1 d . .
F4 F 0.48251(15) 0.59750(8) -0.0343(2) 0.0700(5) Uani 1 1 d . .
D3 D 0.834(3) 0.7211(18) 0.047(3) 0.105(10) Uiso 1 1 d . .
N1 N 0.8632(2) 0.62400(11) 0.3530(2) 0.0501(5) Uani 1 1 d . .
D1A D 0.7930 0.6592 0.3211 0.075 Uiso 1 1 calc R U
D1B D 0.9327 0.6331 0.3109 0.075 Uiso 1 1 calc R U
D1C D 0.9036 0.6250 0.4579 0.075 Uiso 1 1 calc R U
O1 O 0.07759(18) 0.65007(11) 0.2148(2) 0.0675(6) Uani 1 1 d . .
O2 O -0.03257(17) 0.73642(11) 0.0330(2) 0.0624(5) Uani 1 1 d . .
O3 O 0.72843(18) 0.70605(12) 0.0635(2) 0.0687(6) Uani 1 1 d . .
O4 O 0.61983(17) 0.78324(11) -0.1363(2) 0.0596(5) Uani 1 1 d . .
O5 O 0.8290(2) 0.57498(13) 0.6227(2) 0.0895(7) 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'
F F 0.0171 0.0103 '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 C1 O2 127.61(19)
O1 C1 C2 118.8(2)
O2 C1 C2 113.6(2)
C7 C2 C3 116.65(17)
C7 C2 C1 121.8(2)
C3 C2 C1 121.5(2)
F3 C3 C4 118.1(2)
F3 C3 C2 120.39(18)
C4 C3 C2 121.5(2)
F4 C4 C3 118.3(2)
F4 C4 C5 120.32(17)
C3 C4 C5 121.4(2)
C6 C5 C4 117.03(17)
C6 C5 C8 120.7(2)
C4 C5 C8 122.3(2)
F2 C6 C7 118.6(2)
F2 C6 C5 119.62(17)
C7 C6 C5 121.7(2)
F1 C7 C6 118.2(2)
F1 C7 C2 119.97(17)
C6 C7 C2 121.8(2)
O4 C8 O3 126.12(19)
O4 C8 C5 120.6(2)
O3 C8 C5 113.3(2)
O5 C10 C11 109.6(2)
C10 C11 C12 114.7(2)
N1 C12 C11 112.2(2)
C9 O5 C10 114.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.214(3)
C1 O2 1.264(3)
C1 C2 1.523(3)
C2 C7 1.377(3)
C2 C3 1.387(3)
C3 F3 1.342(3)
C3 C4 1.379(3)
C4 F4 1.345(2)
C4 C5 1.379(3)
C5 C6 1.377(3)
C5 C8 1.513(3)
C6 F2 1.346(3)
C6 C7 1.373(3)
C7 F1 1.347(2)
C8 O4 1.200(3)
C8 O3 1.283(3)
C9 O5 1.380(4)
C10 O5 1.405(3)
C10 C11 1.489(4)
C11 C12 1.501(3)
C12 N1 1.489(3)
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
C11 H11A O4 0.97 2.61 3.379(3) 136.7 4_576
O3 D3 O1 1.11(3) 2.62(3) 3.308(2) 119(2) 1_655
O3 D3 O2 1.11(3) 1.36(3) 2.467(2) 177(3) 1_655
N1 D1A O3 0.89 2.34 2.874(3) 118.7 .
N1 D1A O4 0.89 2.10 2.888(2) 147.3 4_576
N1 D1B O1 0.89 1.90 2.792(2) 177.9 1_655
N1 D1C O5 0.89 2.06 2.708(3) 128.7 .
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
O1 C1 C2 C7 -128.1(3)
O2 C1 C2 C7 52.6(3)
O1 C1 C2 C3 51.5(3)
O2 C1 C2 C3 -127.7(3)
C7 C2 C3 F3 -179.0(2)
C1 C2 C3 F3 1.4(3)
C7 C2 C3 C4 -0.2(3)
C1 C2 C3 C4 -179.8(2)
F3 C3 C4 F4 -0.3(3)
C2 C3 C4 F4 -179.1(2)
F3 C3 C4 C5 179.1(2)
C2 C3 C4 C5 0.3(4)
F4 C4 C5 C6 179.0(2)
C3 C4 C5 C6 -0.3(3)
F4 C4 C5 C8 -3.1(3)
C3 C4 C5 C8 177.5(2)
C4 C5 C6 F2 177.7(2)
C8 C5 C6 F2 -0.2(3)
C4 C5 C6 C7 0.3(4)
C8 C5 C6 C7 -177.6(2)
F2 C6 C7 F1 0.7(3)
C5 C6 C7 F1 178.0(2)
F2 C6 C7 C2 -177.6(2)
C5 C6 C7 C2 -0.2(4)
C3 C2 C7 F1 -178.1(2)
C1 C2 C7 F1 1.6(3)
C3 C2 C7 C6 0.2(3)
C1 C2 C7 C6 179.8(2)
C6 C5 C8 O4 -58.8(3)
C4 C5 C8 O4 123.4(3)
C6 C5 C8 O3 121.0(3)
C4 C5 C8 O3 -56.8(3)
O5 C10 C11 C12 52.6(3)
C10 C11 C12 N1 -69.3(3)
C11 C10 O5 C9 164.3(3)
