#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:32:52 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/73/7227366.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_7227366
loop_
_publ_author_name
'Kolesnikova, Inna N.'
'Rykov, Anatolii N.'
'Shishkov, Igor F.'
'Tafeenko, Victor A.'
'Aslanov, Leonid A.'
_publ_section_title
;
 Molecular structure of clonidine: gas-phase electron diffraction,
 single-crystal X-ray diffraction and quantum chemical studies.
;
_journal_issue                   6
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              4618
_journal_page_last               4626
_journal_paper_doi               10.1039/c6cp08401j
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C9 H9 Cl2 N3'
_chemical_formula_sum            'C9 H9 Cl2 N3'
_chemical_formula_weight         230.09
_chemical_name_common            Clonidine
_chemical_name_systematic        2-(2,6-dichlorophenylamino)-2-imidazoline
_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
;
2016-12-07 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.0720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.84330(10)
_cell_length_b                   8.2767(3)
_cell_length_c                   15.1223(6)
_cell_measurement_reflns_used    1687
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      65.5
_cell_measurement_theta_min      2.3
_cell_volume                     2022.88(11)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector                 Pilatus100K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  STOE
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.765
_diffrn_reflns_theta_min         5.040
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.463
_exptl_absorpt_correction_T_max  0.4430
_exptl_absorpt_correction_T_min  0.3881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.894
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0402
_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)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2449
_reflns_number_total             3994
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cp08401j2.cif
_cod_data_source_block           clonidine
_cod_depositor_comments          'Adding full bibliography for 7227366.cif.'
_cod_database_code               7227366
_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
_atom_site_refinement_flags_occupancy
Cl19 Cl 0.24560(10) 0.37161(18) 0.25313(12) 0.0631(6) Uani 0.935(3) 1 d D . P
Cl23 Cl 0.42670(11) 0.91309(18) 0.39802(14) 0.0725(6) Uani 1 1 d D . .
N1 N 0.4222(2) 0.4167(4) 0.2510(3) 0.0494(10) Uani 1 1 d . . .
N3 N 0.4994(3) 0.3572(5) 0.4057(3) 0.0581(11) Uani 1 1 d . . .
N6 N 0.4063(3) 0.5628(5) 0.3820(4) 0.0421(11) Uani 1 1 d . . .
C2 C 0.4381(2) 0.4523(5) 0.3469(3) 0.0435(12) Uani 1 1 d . . .
C4 C 0.5341(5) 0.2606(6) 0.3488(6) 0.0548(19) Uani 1 1 d . . .
H4A H 0.5480 0.1517 0.3742 0.066 Uiso 1 1 calc R U .
H4B H 0.5825 0.3118 0.3474 0.066 Uiso 1 1 calc R U .
C5 C 0.4615(5) 0.2622(6) 0.2495(6) 0.0543(19) Uani 1 1 d . . .
H5A H 0.4797 0.2590 0.1975 0.065 Uiso 1 1 calc R U .
H5B H 0.4244 0.1723 0.2419 0.065 Uiso 1 1 calc R U .
C7 C 0.3348(3) 0.6499(8) 0.3157(4) 0.0426(14) Uani 1 1 d . . .
C8 C 0.2595(4) 0.5801(3) 0.2564(4) 0.0502(16) Uani 1 1 d D . .
H8 H 0.2548 0.4681 0.2550 0.060 Uiso 0.065(3) 1 calc R U P
C9 C 0.1910(4) 0.6717(9) 0.1993(5) 0.065(2) Uani 1 1 d . . .
H9 H 0.1416 0.6217 0.1588 0.078 Uiso 1 1 calc R U .
C10 C 0.1969(5) 0.8370(11) 0.2034(6) 0.082(3) Uani 1 1 d . . .
H10 H 0.1512 0.8987 0.1645 0.098 Uiso 1 1 calc R U .
C11 C 0.2692(5) 0.9139(8) 0.2640(6) 0.067(2) Uani 1 1 d D . .
H11 H 0.2726 1.0260 0.2681 0.081 Uiso 0.935(3) 1 calc R U P
C12 C 0.3365(2) 0.8176(7) 0.3183(4) 0.0507(16) Uani 1 1 d D . .
Cl1A Cl 0.92456(13) 0.91970(19) 0.52917(15) 0.0772(6) Uani 1 1 d . . .
Cl2A Cl 0.74827(10) 0.37282(18) 0.49658(13) 0.0678(7) Uani 0.958(3) 1 d . . P
N1A N 0.9247(2) 0.4297(5) 0.6719(3) 0.0487(10) Uani 1 1 d . . .
N3A N 0.9999(2) 0.3633(5) 0.5930(3) 0.0513(11) Uani 1 1 d . . .
N6A N 0.9042(3) 0.5686(5) 0.5231(4) 0.0433(11) Uani 1 1 d . . .
C2A C 0.9381(2) 0.4607(5) 0.5902(3) 0.0416(11) Uani 1 1 d . . .
C4A C 1.0341(5) 0.2720(7) 0.6821(6) 0.0564(19) Uani 1 1 d . . .
H41A H 1.0836 0.3230 0.7300 0.068 Uiso 1 1 calc R U .
H41B H 1.0472 0.1625 0.6707 0.068 Uiso 1 1 calc R U .
C5A C 0.9641(4) 0.2746(6) 0.7150(5) 0.0529(18) Uani 1 1 d . . .
H51A H 0.9266 0.1842 0.6885 0.063 Uiso 1 1 calc R U .
H51B H 0.9850 0.2751 0.7856 0.063 Uiso 1 1 calc R U .
C7A C 0.8346(3) 0.6515(7) 0.5161(4) 0.0414(13) Uani 1 1 d . . .
C8A C 0.8358(4) 0.8229(8) 0.5162(5) 0.0538(17) Uani 1 1 d . . .
C9A C 0.7655(6) 0.9111(8) 0.5072(5) 0.067(2) Uani 1 1 d D . .
H91A H 0.7684 1.0236 0.5089 0.080 Uiso 0.9577 1 d . U P
C10A C 0.6940(5) 0.8357(10) 0.4965(5) 0.070(2) Uani 1 1 d . . .
H10A H 0.6484 0.8963 0.4912 0.085 Uiso 1 1 calc R U .
C11A C 0.6899(4) 0.6716(9) 0.4936(5) 0.060(2) Uani 1 1 d . . .
H11A H 0.6413 0.6194 0.4857 0.073 Uiso 1 1 calc R U .
C12A C 0.7581(4) 0.5832(6) 0.5023(4) 0.0494(16) Uani 1 1 d . . .
H12A H 0.7549 0.4650 0.4983 0.059 Uiso 0.0423 1 d . U P
Cl3A Cl 0.748(3) 1.1185(12) 0.501(3) 0.0725(6) Uani 0.042(3) 1 d D . P
H1 H 0.364(3) 0.416(6) 0.202(4) 0.068(14) Uiso 1 1 d . . .
H3 H 0.534(4) 0.392(7) 0.480(5) 0.12(2) Uiso 1 1 d . . .
H1A H 0.876(3) 0.456(6) 0.666(3) 0.067(15) Uiso 1 1 d . . .
H3A H 1.026(3) 0.367(5) 0.553(3) 0.052(12) Uiso 1 1 d . . .
Cl11 Cl 0.2500(14) 1.1209(10) 0.2577(18) 0.0631(6) Uani 0.065(3) 1 d D . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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_3
C8 Cl19 Cl11 170.6(6) 1_545
C2 N1 C5 108.4(4) .
C2 N3 C4 110.8(4) .
C2 N6 C7 118.6(4) .
N6 C2 N3 121.2(4) .
N6 C2 N1 130.1(4) .
N3 C2 N1 108.5(4) .
N3 C4 C5 100.3(5) .
N1 C5 C4 101.9(4) .
C8 C7 C12 116.1(4) .
C8 C7 N6 124.9(5) .
C12 C7 N6 118.6(4) .
C7 C8 C9 122.1(5) .
C7 C8 Cl19 121.3(5) .
C9 C8 Cl19 116.6(5) .
C10 C9 C8 119.1(5) .
C9 C10 C11 121.5(6) .
C10 C11 C12 117.4(6) .
C10 C11 Cl11 108.1(10) .
C12 C11 Cl11 134.4(11) .
C11 C12 C7 123.7(4) .
C11 C12 Cl23 117.7(5) .
C7 C12 Cl23 118.5(4) .
C12A Cl2A Cl3A 174.5(11) 1_545
C2A N1A C5A 109.1(4) .
C2A N3A C4A 111.0(5) .
C2A N6A C7A 120.5(5) .
N6A C2A N3A 122.7(4) .
N6A C2A N1A 129.1(4) .
N3A C2A N1A 108.0(4) .
N3A C4A C5A 102.6(5) .
N1A C5A C4A 99.8(5) .
N6A C7A C12A 126.5(5) .
N6A C7A C8A 118.9(4) .
C12A C7A C8A 114.5(4) .
C9A C8A C7A 120.4(5) .
C9A C8A Cl1A 120.8(5) .
C7A C8A Cl1A 118.8(4) .
C10A C9A C8A 121.6(6) .
C10A C9A Cl3A 107.8(16) .
C8A C9A Cl3A 130.5(16) .
C11A C10A C9A 119.6(5) .
C10A C11A C12A 119.6(5) .
C11A C12A C7A 124.2(6) .
C11A C12A Cl2A 117.3(5) .
C7A C12A Cl2A 118.5(4) .
C9A Cl3A Cl2A 170(3) 1_565
C11 Cl11 Cl19 171.3(14) 1_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl19 C8 1.741(2) .
Cl19 Cl11 2.077(8) 1_545
Cl23 C12 1.739(2) .
N1 C2 1.386(6) .
N1 C5 1.463(6) .
N3 C2 1.336(6) .
N3 C4 1.488(8) .
N6 C2 1.302(6) .
N6 C7 1.438(7) .
C4 C5 1.511(10) .
C7 C8 1.386(8) .
C7 C12 1.389(9) .
C8 C9 1.386(9) .
C9 C10 1.372(13) .
C10 C11 1.381(11) .
C11 C12 1.384(9) .
C11 Cl11 1.741(2) .
Cl1A C8A 1.711(6) .
Cl2A C12A 1.748(5) .
Cl2A Cl3A 2.106(10) 1_545
N1A C2A 1.379(6) .
N1A C5A 1.476(6) .
N3A C2A 1.353(5) .
N3A C4A 1.436(9) .
N6A C2A 1.293(6) .
N6A C7A 1.384(7) .
C4A C5A 1.528(10) .
C7A C12A 1.410(8) .
C7A C8A 1.418(10) .
C8A C9A 1.407(10) .
C9A C10A 1.367(11) .
C9A Cl3A 1.741(2) .
C10A C11A 1.360(13) .
C11A C12A 1.378(8) .
Cl3A Cl2A 2.106(10) 1_565
Cl11 Cl19 2.077(8) 1_565
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
N3 H3 N6 1.07(7) 1.93(7) 3.000(6) 175(5) 3_666
N3A H3A N6A 0.91(5) 2.09(5) 2.977(7) 166(4) 3_766
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_4
C7 N6 C2 N3 -173.6(5) .
C7 N6 C2 N1 10.9(8) .
C4 N3 C2 N6 -170.6(5) .
C4 N3 C2 N1 5.7(6) .
C5 N1 C2 N6 -168.7(5) .
C5 N1 C2 N3 15.3(5) .
C2 N3 C4 C5 -23.1(6) .
C2 N1 C5 C4 -29.0(6) .
N3 C4 C5 N1 29.8(6) .
C2 N6 C7 C8 60.0(8) .
C2 N6 C7 C12 -128.2(5) .
C12 C7 C8 C9 3.1(8) .
N6 C7 C8 C9 175.1(6) .
C12 C7 C8 Cl19 -174.9(4) .
N6 C7 C8 Cl19 -2.9(9) .
C7 C8 C9 C10 -1.9(9) .
Cl19 C8 C9 C10 176.2(4) .
C8 C9 C10 C11 -0.8(8) .
C9 C10 C11 C12 2.0(11) .
C9 C10 C11 Cl11 -174.5(10) .
C10 C11 C12 C7 -0.6(10) .
Cl11 C11 C12 C7 174.7(13) .
C10 C11 C12 Cl23 -177.7(6) .
Cl11 C11 C12 Cl23 -2.5(16) .
C8 C7 C12 C11 -1.9(6) .
N6 C7 C12 C11 -174.4(7) .
C8 C7 C12 Cl23 175.2(5) .
N6 C7 C12 Cl23 2.7(5) .
C7A N6A C2A N3A 172.0(5) .
C7A N6A C2A N1A -12.9(8) .
C4A N3A C2A N6A 171.5(5) .
C4A N3A C2A N1A -4.5(6) .
C5A N1A C2A N6A 168.2(5) .
C5A N1A C2A N3A -16.2(5) .
C2A N3A C4A C5A 22.0(6) .
C2A N1A C5A C4A 28.2(6) .
N3A C4A C5A N1A -28.9(6) .
C2A N6A C7A C12A -58.5(8) .
C2A N6A C7A C8A 125.9(5) .
N6A C7A C8A C9A 178.6(7) .
C12A C7A C8A C9A 2.5(6) .
N6A C7A C8A Cl1A -2.2(6) .
C12A C7A C8A Cl1A -178.3(6) .
C7A C8A C9A C10A -1.1(10) .
Cl1A C8A C9A C10A 179.8(6) .
C7A C8A C9A Cl3A -177.4(19) .
Cl1A C8A C9A Cl3A 3(2) .
C8A C9A C10A C11A -0.5(10) .
Cl3A C9A C10A C11A 176.5(15) .
C9A C10A C11A C12A 0.6(7) .
C10A C11A C12A C7A 1.1(9) .
C10A C11A C12A Cl2A -179.3(4) .
N6A C7A C12A C11A -178.4(6) .
C8A C7A C12A C11A -2.6(8) .
N6A C7A C12A Cl2A 2.0(9) .
C8A C7A C12A Cl2A 177.8(4) .
C10A C9A Cl3A Cl2A 180(100) 1_565
C8A C9A Cl3A Cl2A -4(15) 1_565
