#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:55:44 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/14/7061425.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_7061425
loop_
_publ_author_name
'Li, Jiulong'
'Li, Chang'
'Ji, Xu'
'Sun, Qin'
'Li, Zhi'
'Liu, He'
'Zhou, Lina'
'Jing, Dingding'
'Gong, Junbo'
'Chen, Wei'
_publ_section_title
;
 Combined virtual and experimental screening of multicomponent crystals of
 2,4-dichlorophenoxyacetic acid
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8708
_journal_page_last               8719
_journal_paper_doi               10.1039/D2NJ00536K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C8 H5 Cl2 O3, C3 H5 N'
_chemical_formula_sum            'C11 H10 Cl2 N O3'
_chemical_formula_weight         275.10
_chemical_name_systematic
'hemikis(1,4-phenylenediammonium) 2,4-Dichlorophenoxyacetate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                95.693(5)
_cell_angle_beta                 95.999(6)
_cell_angle_gamma                114.740(7)
_cell_formula_units_Z            2
_cell_length_a                   7.3335(5)
_cell_length_b                   8.0270(5)
_cell_length_c                   10.9917(7)
_cell_measurement_reflns_used    4793
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.9520
_cell_measurement_theta_min      1.8630
_cell_volume                     577.07(7)
_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    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0468933000
_diffrn_orient_matrix_UB_12      0.0578870000
_diffrn_orient_matrix_UB_13      -0.0431430000
_diffrn_orient_matrix_UB_21      -0.0317829000
_diffrn_orient_matrix_UB_22      -0.0794433000
_diffrn_orient_matrix_UB_23      -0.0459448000
_diffrn_orient_matrix_UB_31      -0.0918490000
_diffrn_orient_matrix_UB_32      0.0068721000
_diffrn_orient_matrix_UB_33      -0.0186034000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8728
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.900
_diffrn_reflns_theta_min         1.887
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       plate
_exptl_crystal_F_000             282
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0473
_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)+(0.0568P)²+0.2132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1257
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3038
_reflns_number_total             3895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00536k2.cif
_cod_data_source_block           r20210704a
_cod_depositor_comments
'Adding full bibliography for 7061422--7061427.cif.'
_cod_database_code               7061425
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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.
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00I), C00D(H00D), C00F(H00F), C00G(H00G)
2.c Idealised Me refined as rotating group:
 N006(H00C,H00E,H00H)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.826
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
Cl01 Cl 0.17595(7) 0.26641(7) 0.38995(4) 0.02899(13) Uani 1 1 d . . . . .
Cl02 Cl 0.41840(8) 0.12671(7) 0.83218(4) 0.03299(14) Uani 1 1 d . . . . .
O1 O 0.64584(18) 0.45697(18) 0.12787(11) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.96633(18) 0.49583(18) 0.16042(12) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.56861(17) 0.31423(18) 0.33756(11) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.7924(2) 0.4447(2) 0.18820(15) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.7674(2) 0.3631(2) 0.30767(15) 0.0191(3) Uani 1 1 d . . . . .
H2A H 0.792632 0.253509 0.299298 0.023 Uiso 1 1 calc R U . . .
H2B H 0.867338 0.453051 0.374794 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5416(2) 0.2661(2) 0.45197(15) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.3577(3) 0.2419(2) 0.49023(16) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.3182(3) 0.1987(2) 0.60652(16) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.195687 0.184126 0.631276 0.027 Uiso 1 1 calc R U . . .
C6 C 0.4647(3) 0.1777(2) 0.68516(16) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.6458(3) 0.1956(2) 0.64877(16) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.741424 0.177964 0.701790 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6838(3) 0.2401(2) 0.53219(16) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.805775 0.252726 0.507462 0.025 Uiso 1 1 calc R U . . .
N1 N 1.2423(2) 0.38484(18) 0.07905(13) 0.0165(3) Uani 1 1 d . . . . .
H1A H 1.173976 0.433096 0.121307 0.020 Uiso 1 1 calc R U . . .
H1B H 1.272562 0.439792 0.012666 0.020 Uiso 1 1 calc R U . . .
H1C H 1.356537 0.402890 0.127043 0.020 Uiso 1 1 calc R U . . .
C9 C 0.9325(2) 0.1284(2) -0.03639(15) 0.0181(3) Uani 1 1 d . . . . .
H6 H 0.888225 0.215037 -0.060253 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1171(2) 0.1857(2) 0.03987(14) 0.0151(3) Uani 1 1 d . . . . .
C11 C 1.1862(2) 0.0603(2) 0.07689(15) 0.0175(3) Uani 1 1 d . . . . .
H7 H 1.310651 0.101435 0.128345 0.021 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_publ_flag
C3 O3 C2 115.82(13) . . ?
O1 C1 C2 119.94(14) . . ?
O2 C1 O1 125.85(15) . . ?
O2 C1 C2 114.21(14) . . ?
O3 C2 C1 111.82(13) . . ?
O3 C2 H2A 109.3 . . ?
O3 C2 H2B 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
O3 C3 C4 117.04(15) . . ?
O3 C3 C8 124.56(15) . . ?
C8 C3 C4 118.40(15) . . ?
C3 C4 Cl01 119.07(13) . . ?
C5 C4 Cl01 119.50(13) . . ?
C5 C4 C3 121.43(16) . . ?
C4 C5 H3 120.6 . . ?
C6 C5 C4 118.72(16) . . ?
C6 C5 H3 120.6 . . ?
C5 C6 Cl02 119.15(14) . . ?
C7 C6 Cl02 119.60(14) . . ?
C7 C6 C5 121.25(16) . . ?
C6 C7 H4 120.3 . . ?
C6 C7 C8 119.34(16) . . ?
C8 C7 H4 120.3 . . ?
C3 C8 H5 119.6 . . ?
C7 C8 C3 120.81(16) . . ?
C7 C8 H5 119.6 . . ?
H1B N1 H1A 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H1C N1 H1A 109.5 . . ?
C10 N1 H1A 109.5 . . ?
C10 N1 H1B 109.5 . . ?
C10 N1 H1C 109.5 . . ?
C10 C9 H6 120.4 . . ?
C10 C9 C11 119.17(15) . 2_755 ?
C11 C9 H6 120.4 2_755 . ?
C9 C10 N1 118.44(14) . . ?
C11 C10 N1 119.91(14) . . ?
C11 C10 C9 121.63(15) . . ?
C9 C11 H7 120.4 2_755 . ?
C10 C11 C9 119.20(15) . 2_755 ?
C10 C11 H7 120.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C4 1.7281(17) . ?
Cl02 C6 1.7389(17) . ?
O1 C1 1.248(2) . ?
O2 C1 1.248(2) . ?
O3 C2 1.426(2) . ?
O3 C3 1.3617(19) . ?
C1 C2 1.519(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.396(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.385(2) . ?
C5 H3 0.9300 . ?
C5 C6 1.384(3) . ?
C7 C6 1.381(3) . ?
C7 H4 0.9300 . ?
C8 C7 1.389(2) . ?
C8 H5 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C10 1.461(2) . ?
C9 H6 0.9300 . ?
C10 C9 1.383(2) . ?
C11 C9 1.390(2) 2_755 ?
C11 C10 1.379(2) . ?
C11 H7 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C4 C5 C6 179.33(13) . . . . ?
O1 C1 C2 O3 -1.8(2) . . . . ?
O2 C1 C2 O3 177.57(14) . . . . ?
O3 C3 C4 Cl01 2.1(2) . . . . ?
O3 C3 C4 C5 -177.93(15) . . . . ?
O3 C3 C8 C7 178.38(16) . . . . ?
C2 O3 C3 C4 171.64(15) . . . . ?
C2 O3 C3 C8 -8.3(2) . . . . ?
C3 O3 C2 C1 -170.57(14) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C8 C7 C6 -0.2(3) . . . . ?
C4 C3 C8 C7 -1.6(2) . . . . ?
C4 C5 C6 Cl02 179.10(14) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C8 C3 C4 Cl01 -177.98(13) . . . . ?
C8 C3 C4 C5 2.0(3) . . . . ?
C8 C7 C6 Cl02 -178.66(13) . . . . ?
C8 C7 C6 C5 1.6(3) . . . . ?
N1 C10 C9 C11 178.48(14) . . . 2_755 ?
C9 C11 C10 N1 -178.45(14) 2_755 . . . ?
C9 C11 C10 C9 0.1(3) 2_755 . . . ?
C11 C10 C9 C11 -0.1(3) . . . 2_755 ?
