#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:00:45 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296436 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572910.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_1572910
loop_
_publ_author_name
'Limberg, Niklas'
'Rautiainen, J. Mikko'
'Lundell, Jan'
'Riedel, Sebastian'
'Rissanen, Kari'
'Puttreddy, Rakesh'
_publ_section_title
;
 Dichlorine-pyridine N-oxide halogen-bonded complexes.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              18840
_journal_page_last               18845
_journal_paper_doi               10.1039/d4sc06270a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'Cl3, C14 H19 N2 O4'
_chemical_formula_sum            'C14 H19 Cl3 N2 O4'
_chemical_formula_weight         385.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-09-11
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-13 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8112(5)
_cell_length_b                   8.9258(3)
_cell_length_c                   17.6828(8)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.92
_cell_volume                     1771.16(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2205
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.322
_diffrn_reflns_theta_min         2.916
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.675911
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1343 before and 0.0629 after correction.
 The Ratio of minimum to maximum transmission is 0.91.

Final HKLF 4 output contains 73828 reflections, Rint = 0.0904
 (37887 with I > 3sig(I), Rint = 0.0766)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.677
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0363
_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)+(0.0426P)²+2.2100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1955
_reflns_number_total             2205
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06270a3.cif
_cod_data_source_block           OGH_D49_34
_cod_depositor_comments
'Adding full bibliography for 1572907--1572916.cif.'
_cod_database_code               1572910
_shelx_shelxl_version_number     2019/1
_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_max   0.909
_shelx_estimated_absorpt_t_min   0.713
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4)
1.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
'-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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.500000 0.40252(6) 0.250000 0.02694(14) Uani 1 2 d S T P . .
Cl3 Cl 0.500000 0.66079(6) 0.250000 0.03308(15) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 0.14779(7) 0.250000 0.03708(16) Uani 1 2 d S T P . .
O2 O 0.61122(9) 0.11530(11) 0.52969(6) 0.0228(2) Uani 1 1 d . . . . .
O1 O 0.65878(10) 0.71873(11) 0.51373(7) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.65499(10) 0.56659(14) 0.52035(8) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.61055(12) 0.48556(17) 0.45283(8) 0.0210(3) Uani 1 1 d . . . . .
H1A H 0.588367 0.534618 0.402661 0.025 Uiso 1 1 calc R U . . .
C5 C 0.68909(12) 0.50295(17) 0.59332(9) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.59735(12) 0.33418(16) 0.45619(9) 0.0206(3) Uani 1 1 d . . . . .
H2 H 0.567524 0.277156 0.408745 0.025 Uiso 1 1 calc R U . . .
C3 C 0.62853(12) 0.26411(15) 0.53080(8) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.67497(12) 0.34989(16) 0.59904(8) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.697126 0.303258 0.649862 0.025 Uiso 1 1 calc R U . . .
C6 C 0.73940(15) 0.60268(18) 0.66342(10) 0.0299(3) Uani 1 1 d . . . . .
H6A H 0.808804 0.655985 0.657693 0.045 Uiso 1 1 calc R U . . .
H6B H 0.763649 0.542254 0.712109 0.045 Uiso 1 1 calc R U . . .
H6C H 0.678819 0.675354 0.666528 0.045 Uiso 1 1 calc R U . . .
C7 C 0.62750(15) 0.04152(17) 0.60469(9) 0.0278(3) Uani 1 1 d . . . . .
H7A H 0.607716 -0.064929 0.595419 0.042 Uiso 1 1 calc R U . . .
H7B H 0.575193 0.087456 0.631630 0.042 Uiso 1 1 calc R U . . .
H7C H 0.710677 0.051790 0.638089 0.042 Uiso 1 1 calc R U . . .
H1 H 0.750000 0.750000 0.500000 0.074(13) Uiso 1 2 d S . 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'
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
Cl1 Cl2 Cl3 180.0 . . ?
C3 O2 C7 117.59(12) . . ?
N1 O1 H1 107.59(9) . . ?
C1 N1 O1 118.03(12) . . ?
C5 N1 O1 119.48(13) . . ?
C5 N1 C1 122.39(13) . . ?
N1 C1 H1A 119.7 . . ?
N1 C1 C2 120.61(13) . . ?
C2 C1 H1A 119.7 . . ?
N1 C5 C4 118.55(13) . . ?
N1 C5 C6 117.76(14) . . ?
C4 C5 C6 123.68(14) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.88(13) . . ?
C3 C2 H2 120.6 . . ?
O2 C3 C2 115.68(13) . . ?
O2 C3 C4 125.08(13) . . ?
C4 C3 C2 119.23(13) . . ?
C5 C4 C3 120.30(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
Cl2 Cl3 2.3053(8) . ?
Cl2 Cl1 2.2737(8) . ?
O2 C3 1.3431(17) . ?
O2 C7 1.4387(18) . ?
O1 N1 1.3650(16) . ?
O1 H1 1.2087(11) . ?
N1 C1 1.3539(19) . ?
N1 C5 1.3512(19) . ?
C1 H1A 0.9500 . ?
C1 C2 1.364(2) . ?
C5 C4 1.384(2) . ?
C5 C6 1.491(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(2) . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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
O2 C3 C4 C5 179.99(13) . . . . ?
O1 N1 C1 C2 -175.70(12) . . . . ?
O1 N1 C5 C4 174.53(12) . . . . ?
O1 N1 C5 C6 -5.11(19) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
N1 C5 C4 C3 1.1(2) . . . . ?
C1 N1 C5 C4 -1.8(2) . . . . ?
C1 N1 C5 C6 178.61(13) . . . . ?
C1 C2 C3 O2 178.85(12) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C5 N1 C1 C2 0.6(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C6 C5 C4 C3 -179.30(14) . . . . ?
C7 O2 C3 C2 -172.28(12) . . . . ?
C7 O2 C3 C4 8.4(2) . . . . ?
