#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:09:45 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/17/1551779.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_1551779
loop_
_publ_author_name
'KAWAMURA, Tomoko'
'HIRAYAMA, Noriaki'
_publ_section_title
;
 Addendum: Crystal Structure of Guanfacine Hydrochloride [X-ray Structure
 Analysis Online, Vol. 25, p. 3 (2009)]
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              47
_journal_paper_doi               10.2116/xraystruct.25.47
_journal_volume                  25
_journal_year                    2009
_chemical_formula_moiety         'C9 H10 Cl3 N3 O '
_chemical_formula_sum            'C9 H10 Cl3 N3 O'
_chemical_formula_weight         282.56
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   14.439(3)
_cell_length_b                   8.3664(18)
_cell_length_c                   39.656(8)
_cell_measurement_reflns_used    38282
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      68.6
_cell_measurement_theta_min      3.1
_cell_volume                     4790.5(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.083
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            34984
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    6.800
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_correction_T_min  0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             2304.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     309
_refine_ls_number_reflns         1736
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                1702
_reflns_number_total             4218
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            25_47_1.cif
_cod_data_source_block           '_Guanfacine_Hydrochloride'
_cod_original_cell_volume        4790.6(17)
_cod_original_formula_sum        'C9 H10 Cl3 N3 O '
_cod_database_code               1551779
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,-Y,1/2+Z
4 1/2-X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,+Y,1/2-Z
8 1/2+X,1/2+Y,1/2-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl(101) Cl 0.6304(2) -0.2464(3) 0.22487(8) 0.0802(10) Uani 1.00 1 d .
Cl(102) Cl 0.6276(2) 0.3692(3) 0.18438(6) 0.0762(10) Uani 1.00 1 d .
Cl(103) Cl 0.73404(16) 0.3273(2) 0.08480(6) 0.0542(7) Uani 1.00 1 d .
Cl(202) Cl 0.57042(17) 0.6378(2) 0.12507(6) 0.0588(8) Uani 1.00 1 d .
Cl(201) Cl 0.25653(19) 0.3108(3) 0.09875(6) 0.0686(9) Uani 1.00 1 d .
Cl(203) Cl 0.36988(18) 0.0771(2) 0.01690(6) 0.0522(7) Uani 1.00 1 d .
O(101) O 0.4890(4) 0.0330(8) 0.15882(16) 0.062(2) Uani 1.00 1 d .
O(201) O 0.4123(4) 0.6773(8) 0.05502(14) 0.059(2) Uani 1.00 1 d .
N(101) N 0.5904(4) 0.0215(8) 0.11462(17) 0.038(2) Uani 1.00 1 d .
N(102) N 0.5662(5) -0.0017(9) 0.05832(18) 0.059(2) Uani 1.00 1 d .
N(103) N 0.4402(5) 0.0170(8) 0.09335(19) 0.046(2) Uani 1.00 1 d .
N(201) N 0.3943(5) 0.4525(8) 0.02341(18) 0.043(2) Uani 1.00 1 d .
N(202) N 0.3435(5) 0.4175(8) -0.03101(18) 0.056(2) Uani 1.00 1 d .
N(203) N 0.3635(5) 0.6698(9) -0.01107(17) 0.050(2) Uani 1.00 1 d .
C(101) C 0.5672(7) 0.0273(11) 0.1487(2) 0.045(3) Uani 1.00 1 d .
C(102) C 0.6507(6) 0.0184(11) 0.1707(2) 0.053(3) Uani 1.00 1 d .
C(103) C 0.6342(6) 0.0662(11) 0.2071(2) 0.040(2) Uani 1.00 1 d .
C(104) C 0.6287(6) -0.0420(10) 0.2333(2) 0.051(3) Uani 1.00 1 d .
C(105) C 0.6165(7) 0.0030(15) 0.2664(2) 0.062(3) Uani 1.00 1 d .
C(106) C 0.6137(7) 0.1650(16) 0.2735(2) 0.063(3) Uani 1.00 1 d .
C(107) C 0.6178(6) 0.2774(12) 0.2485(2) 0.058(3) Uani 1.00 1 d .
C(108) C 0.6271(6) 0.2258(13) 0.2155(2) 0.050(3) Uani 1.00 1 d .
C(109) C 0.5298(7) 0.0113(11) 0.0891(2) 0.040(2) Uani 1.00 1 d .
C(201) C 0.4162(6) 0.5325(12) 0.0521(2) 0.043(3) Uani 1.00 1 d .
C(202) C 0.4491(6) 0.4238(11) 0.0807(2) 0.046(3) Uani 1.00 1 d .
C(203) C 0.4116(6) 0.4761(10) 0.1146(2) 0.036(2) Uani 1.00 1 d .
C(208) C 0.4599(6) 0.5721(10) 0.1367(2) 0.039(2) Uani 1.00 1 d .
C(207) C 0.4257(7) 0.6178(12) 0.1674(2) 0.054(3) Uani 1.00 1 d .
C(206) C 0.3403(8) 0.5672(13) 0.1769(2) 0.066(4) Uani 1.00 1 d .
C(205) C 0.2875(7) 0.4683(12) 0.1560(2) 0.059(3) Uani 1.00 1 d .
C(204) C 0.3238(7) 0.4268(10) 0.1249(2) 0.046(3) Uani 1.00 1 d .
C(209) C 0.3666(6) 0.5188(11) -0.0063(2) 0.035(2) Uani 1.00 1 d .
H(101) H 0.6960 0.0883 0.1616 0.064 Uiso 1.00 1 c R
H(102) H 0.6738 -0.0880 0.1706 0.064 Uiso 1.00 1 c R
H(103) H 0.6111 -0.0749 0.2837 0.075 Uiso 1.00 1 c R
H(104) H 0.6087 0.1979 0.2963 0.076 Uiso 1.00 1 c R
H(105) H 0.6135 0.3880 0.2537 0.069 Uiso 1.00 1 c R
H(106) H 0.6564 0.0121 0.1071 0.046 Uiso 1.00 1 c R
H(107) H 0.6296 -0.0289 0.0620 0.071 Uiso 1.00 1 c R
H(108) H 0.5366 -0.0559 0.0420 0.071 Uiso 1.00 1 c R
H(109) H 0.4040 -0.0553 0.0822 0.056 Uiso 1.00 1 c R
H(110) H 0.4200 0.0827 0.1172 0.056 Uiso 1.00 1 c R
H(201) H 0.4288 0.3178 0.0764 0.055 Uiso 1.00 1 c R
H(202) H 0.5148 0.4263 0.0814 0.055 Uiso 1.00 1 c R
H(203) H 0.4611 0.6851 0.1818 0.065 Uiso 1.00 1 c R
H(204) H 0.3154 0.5988 0.1980 0.079 Uiso 1.00 1 c R
H(205) H 0.2287 0.4286 0.1628 0.071 Uiso 1.00 1 c R
H(206) H 0.4154 0.3195 0.0250 0.052 Uiso 1.00 1 c R
H(207) H 0.3423 0.3108 -0.0268 0.067 Uiso 1.00 1 c R
H(208) H 0.3330 0.4718 -0.0474 0.067 Uiso 1.00 1 c R
H(209) H 0.3525 0.7186 -0.0284 0.060 Uiso 1.00 1 c R
H(210) H 0.3753 0.7436 0.0039 0.060 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.364 0.702
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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
C(101) N(101) C(109) 125.2(7)
C(201) N(201) C(209) 126.4(7)
O(101) C(101) N(101) 123.6(8)
O(101) C(101) C(102) 124.5(8)
N(101) C(101) C(102) 111.8(8)
C(101) C(102) C(103) 114.7(7)
C(102) C(103) C(104) 123.5(8)
C(102) C(103) C(108) 119.8(8)
C(104) C(103) C(108) 116.7(8)
Cl(101) C(104) C(103) 119.9(7)
Cl(101) C(104) C(105) 117.0(8)
C(103) C(104) C(105) 123.0(9)
C(104) C(105) C(106) 117.6(10)
C(105) C(106) C(107) 121.8(10)
C(106) C(107) C(108) 118.2(10)
Cl(102) C(108) C(103) 120.1(7)
Cl(102) C(108) C(107) 117.4(8)
C(103) C(108) C(107) 122.5(9)
N(101) C(109) N(102) 116.0(8)
N(101) C(109) N(103) 123.3(8)
N(102) C(109) N(103) 120.7(8)
O(201) C(201) N(201) 124.0(9)
O(201) C(201) C(202) 122.4(8)
N(201) C(201) C(202) 113.7(8)
C(201) C(202) C(203) 112.1(7)
C(202) C(203) C(208) 123.5(8)
C(202) C(203) C(204) 120.1(8)
C(208) C(203) C(204) 116.4(8)
Cl(202) C(208) C(203) 118.5(7)
Cl(202) C(208) C(207) 118.4(7)
C(203) C(208) C(207) 123.1(8)
C(208) C(207) C(206) 119.0(9)
C(207) C(206) C(205) 121.3(10)
C(206) C(205) C(204) 117.9(9)
Cl(201) C(204) C(203) 120.1(7)
Cl(201) C(204) C(205) 117.7(7)
C(203) C(204) C(205) 122.2(8)
N(201) C(209) N(202) 116.7(7)
N(201) C(209) N(203) 122.8(8)
N(202) C(209) N(203) 120.6(8)
C(101) N(101) H(106) 121.4
C(109) N(101) H(106) 113.1
C(109) N(102) H(107) 105.0
C(109) N(102) H(108) 120.9
H(107) N(102) H(108) 116.5
C(109) N(103) H(109) 118.7
C(109) N(103) H(110) 112.3
H(109) N(103) H(110) 125.4
C(201) N(201) H(206) 111.5
C(209) N(201) H(206) 121.1
C(209) N(202) H(207) 119.6
C(209) N(202) H(208) 106.3
H(207) N(202) H(208) 134.1
C(209) N(203) H(209) 128.8
C(209) N(203) H(210) 126.2
H(209) N(203) H(210) 105.0
C(101) C(102) H(101) 107.5
C(101) C(102) H(102) 109.1
C(103) C(102) H(101) 108.1
C(103) C(102) H(102) 107.9
H(101) C(102) H(102) 109.5
C(104) C(105) H(103) 120.8
C(106) C(105) H(103) 121.6
C(105) C(106) H(104) 118.6
C(107) C(106) H(104) 119.6
C(106) C(107) H(105) 120.6
C(108) C(107) H(105) 121.1
C(201) C(202) H(201) 109.0
C(201) C(202) H(202) 108.7
C(203) C(202) H(201) 108.7
C(203) C(202) H(202) 108.9
H(201) C(202) H(202) 109.5
C(208) C(207) H(203) 120.4
C(206) C(207) H(203) 120.6
C(207) C(206) H(204) 120.0
C(205) C(206) H(204) 118.7
C(206) C(205) H(205) 121.8
C(204) C(205) H(205) 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl(101) C(104) 1.743(9)
Cl(102) C(108) 1.722(10)
Cl(202) C(208) 1.750(9)
Cl(201) C(204) 1.722(9)
O(101) C(101) 1.200(12)
O(201) C(201) 1.218(12)
N(101) C(101) 1.393(11)
N(101) C(109) 1.340(11)
N(102) C(109) 1.336(11)
N(103) C(109) 1.306(12)
N(201) C(201) 1.358(12)
N(201) C(209) 1.361(11)
N(202) C(209) 1.338(11)
N(203) C(209) 1.279(11)
C(101) C(102) 1.491(13)
C(102) C(103) 1.517(12)
C(103) C(104) 1.381(13)
C(103) C(108) 1.380(14)
C(104) C(105) 1.377(15)
C(105) C(106) 1.384(18)
C(106) C(107) 1.366(16)
C(107) C(108) 1.384(14)
C(201) C(202) 1.529(13)
C(202) C(203) 1.512(12)
C(203) C(208) 1.378(13)
C(203) C(204) 1.396(13)
C(208) C(207) 1.371(14)
C(207) C(206) 1.356(16)
C(206) C(205) 1.396(15)
C(205) C(204) 1.384(13)
N(101) H(106) 1.002
N(102) H(107) 0.953
N(102) H(108) 0.900
N(103) H(109) 0.914
N(103) H(110) 1.132
N(201) H(206) 1.155
N(202) H(207) 0.908
N(202) H(208) 0.807
N(203) H(209) 0.816
N(203) H(210) 0.874
C(102) H(101) 0.950
C(102) H(102) 0.950
C(105) H(103) 0.950
C(106) H(104) 0.950
C(107) H(105) 0.950
C(202) H(201) 0.950
C(202) H(202) 0.950
C(207) H(203) 0.950
C(206) H(204) 0.950
C(205) H(205) 0.950
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
C(101) N(101) C(109) N(102) -176.4(8)
C(101) N(101) C(109) N(103) 5.1(14)
C(109) N(101) C(101) O(101) -4.5(15)
C(109) N(101) C(101) C(102) 173.0(8)
C(201) N(201) C(209) N(202) -176.5(8)
C(201) N(201) C(209) N(203) 4.3(14)
C(209) N(201) C(201) O(201) 1.3(14)
C(209) N(201) C(201) C(202) -177.3(8)
O(101) C(101) C(102) C(103) -17.5(14)
N(101) C(101) C(102) C(103) 165.0(8)
C(101) C(102) C(103) C(104) 105.1(10)
C(101) C(102) C(103) C(108) -77.2(11)
C(102) C(103) C(104) Cl(101) -5.8(12)
C(102) C(103) C(104) C(105) 178.0(9)
C(102) C(103) C(108) Cl(102) 5.3(12)
C(102) C(103) C(108) C(107) -175.9(8)
C(104) C(103) C(108) Cl(102) -176.9(7)
C(104) C(103) C(108) C(107) 1.9(14)
C(108) C(103) C(104) Cl(101) 176.4(7)
C(108) C(103) C(104) C(105) 0.2(10)
Cl(101) C(104) C(105) C(106) -179.2(7)
C(103) C(104) C(105) C(106) -2.9(14)
C(104) C(105) C(106) C(107) 3.6(15)
C(105) C(106) C(107) C(108) -1.6(15)
C(106) C(107) C(108) Cl(102) 177.5(7)
C(106) C(107) C(108) C(103) -1.3(14)
O(201) C(201) C(202) C(203) 41.2(12)
N(201) C(201) C(202) C(203) -140.2(8)
C(201) C(202) C(203) C(208) -95.6(10)
C(201) C(202) C(203) C(204) 84.6(10)
C(202) C(203) C(208) Cl(202) 0.1(9)
C(202) C(203) C(208) C(207) -179.4(9)
C(202) C(203) C(204) Cl(201) -1.7(12)
C(202) C(203) C(204) C(205) 178.3(8)
C(208) C(203) C(204) Cl(201) 178.4(6)
C(208) C(203) C(204) C(205) -1.5(13)
C(204) C(203) C(208) Cl(202) -180.0(6)
C(204) C(203) C(208) C(207) 0.5(12)
Cl(202) C(208) C(207) C(206) -179.7(7)
C(203) C(208) C(207) C(206) -0.1(12)
C(208) C(207) C(206) C(205) 0.9(16)
C(207) C(206) C(205) C(204) -1.9(16)
C(206) C(205) C(204) Cl(201) -177.7(8)
C(206) C(205) C(204) C(203) 2.3(14)
