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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520421.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_1520421
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C10H21Cl3N6O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              626
_journal_year                    2009
_chemical_formula_sum            'C10 H21 Cl3 N6 O'
_chemical_formula_weight         347.68
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.045(3)
_cell_angle_beta                 107.440(3)
_cell_angle_gamma                116.265(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9934(10)
_cell_length_b                   10.0238(11)
_cell_length_c                   10.5796(12)
_cell_measurement_reflns_used    32642
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     778.78(16)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11636
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0847
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+4.3652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1981
_reflns_number_gt                2550
_reflns_number_total             3520
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-626.cif
_cod_data_source_block           2008src1280
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/626)

More at:
http://ecrystals.chem.soton.ac.uk/626/
;
_cod_original_cell_volume        778.78(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520421
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C -0.5416(7) -0.1837(6) 0.0792(5) 0.0245(11) Uani 1 1 d . . .
H2A H -0.4357 -0.1949 0.0860 0.029 Uiso 1 1 calc R . .
H2B H -0.6054 -0.1929 -0.0184 0.029 Uiso 1 1 calc R . .
C3 C -0.6669(7) -0.3110(6) 0.1224(6) 0.0252(11) Uani 1 1 d . . .
H3A H -0.7126 -0.4140 0.0584 0.030 Uiso 1 1 calc R . .
H3B H -0.5999 -0.3076 0.2172 0.030 Uiso 1 1 calc R . .
C5 C -0.7638(7) -0.1312(6) 0.2053(5) 0.0238(11) Uani 1 1 d . . .
H5 H -0.7042 -0.1178 0.3050 0.029 Uiso 1 1 calc R . .
H5B H -0.8708 -0.1196 0.1916 0.029 Uiso 1 1 calc R . .
C6 C -0.6341(7) -0.0095(6) 0.1608(5) 0.0219(11) Uani 1 1 d . . .
H6A H -0.6986 -0.0165 0.0640 0.026 Uiso 1 1 calc R . .
H6B H -0.5895 0.0955 0.2207 0.026 Uiso 1 1 calc R . .
C7 C -0.3194(7) 0.0493(6) 0.2813(5) 0.0194(10) Uani 1 1 d . . .
C8 C -0.1687(7) 0.0346(6) 0.2897(5) 0.0225(11) Uani 1 1 d . . .
H8 H -0.1793 -0.0397 0.2174 0.027 Uiso 1 1 calc R . .
C9 C -0.0077(7) 0.1257(6) 0.4003(5) 0.0225(11) Uani 1 1 d . . .
H9 H 0.0931 0.1138 0.4062 0.027 Uiso 1 1 calc R . .
C10 C 0.0083(7) 0.2382(6) 0.5063(5) 0.0202(10) Uani 1 1 d . . .
C11 C -0.1384(7) 0.2493(6) 0.4984(5) 0.0213(11) Uani 1 1 d . . .
H11 H -0.1291 0.3241 0.5695 0.026 Uiso 1 1 calc R . .
C14 C 0.3155(7) 0.4557(6) 0.6193(5) 0.0220(11) Uani 1 1 d . . .
N1 N -0.4808(6) -0.0300(5) 0.1698(4) 0.0225(9) Uani 1 1 d . . .
N4 N -0.8213(6) -0.2903(5) 0.1198(5) 0.0252(10) Uani 1 1 d . . .
H4A H -0.8915 -0.3643 0.1524 0.030 Uiso 1 1 calc R . .
H4B H -0.8913 -0.3068 0.0294 0.030 Uiso 1 1 calc R . .
N12 N -0.2998(6) 0.1534(5) 0.3886(4) 0.0194(9) Uani 1 1 d . . .
H12 H -0.3949 0.1595 0.3873 0.023 Uiso 1 1 calc R . .
N13 N 0.1764(6) 0.3367(5) 0.6249(4) 0.0220(9) Uani 1 1 d . . .
H13 H 0.1867 0.3164 0.7046 0.026 Uiso 1 1 calc R . .
N15 N 0.3107(6) 0.4886(5) 0.5008(5) 0.0243(10) Uani 1 1 d . . .
H15A H 0.2131 0.4302 0.4240 0.029 Uiso 1 1 calc R . .
H15B H 0.4050 0.5687 0.4992 0.029 Uiso 1 1 calc R . .
N16 N 0.4641(6) 0.5429(6) 0.7347(5) 0.0282(11) Uani 1 1 d . . .
H16 H 0.4685 0.5207 0.8131 0.034 Uiso 1 1 calc R . .
H16B H 0.5582 0.6229 0.7325 0.034 Uiso 1 1 calc R . .
O1W O 0.1587(7) 0.1859(6) 0.1634(5) 0.0430(11) Uani 1 1 d D . .
H1W H 0.107(10) 0.235(9) 0.183(7) 0.064 Uiso 1 1 d D . .
H2W H 0.157(11) 0.194(9) 0.084(4) 0.064 Uiso 1 1 d D . .
Cl3 Cl 0.43404(17) 0.17398(15) 0.49990(13) 0.0225(3) Uani 1 1 d . . .
Cl2 Cl 0.23871(18) 0.32166(16) 0.92563(13) 0.0250(3) Uani 1 1 d . . .
Cl1 Cl 0.01285(18) 0.59070(15) 0.79057(13) 0.0253(3) 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'
Cl Cl 0.1484 0.1585 '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
N1 C2 C3 109.8(4) . .
N1 C2 H2A 109.7 . .
C3 C2 H2A 109.7 . .
N1 C2 H2B 109.7 . .
C3 C2 H2B 109.7 . .
H2A C2 H2B 108.2 . .
N4 C3 C2 110.1(4) . .
N4 C3 H3A 109.6 . .
C2 C3 H3A 109.6 . .
N4 C3 H3B 109.6 . .
C2 C3 H3B 109.6 . .
H3A C3 H3B 108.2 . .
N4 C5 C6 108.8(4) . .
N4 C5 H5 109.9 . .
C6 C5 H5 109.9 . .
N4 C5 H5B 109.9 . .
C6 C5 H5B 109.9 . .
H5 C5 H5B 108.3 . .
N1 C6 C5 111.5(4) . .
N1 C6 H6A 109.3 . .
C5 C6 H6A 109.3 . .
N1 C6 H6B 109.3 . .
C5 C6 H6B 109.3 . .
H6A C6 H6B 108.0 . .
N12 C7 N1 118.3(4) . .
N12 C7 C8 117.7(5) . .
N1 C7 C8 124.0(5) . .
C9 C8 C7 120.7(5) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C10 119.4(5) . .
C8 C9 H9 120.3 . .
C10 C9 H9 120.3 . .
C11 C10 C9 119.4(5) . .
C11 C10 N13 119.6(5) . .
C9 C10 N13 121.0(5) . .
C10 C11 N12 120.1(5) . .
C10 C11 H11 119.9 . .
N12 C11 H11 119.9 . .
N13 C14 N15 121.3(5) . .
N13 C14 N16 119.0(5) . .
N15 C14 N16 119.7(5) . .
C7 N1 C6 123.3(4) . .
C7 N1 C2 121.2(4) . .
C6 N1 C2 110.9(4) . .
C3 N4 C5 113.3(4) . .
C3 N4 H4A 108.9 . .
C5 N4 H4A 108.9 . .
C3 N4 H4B 108.9 . .
C5 N4 H4B 108.9 . .
H4A N4 H4B 107.7 . .
C7 N12 C11 122.5(4) . .
C7 N12 H12 118.7 . .
C11 N12 H12 118.7 . .
C14 N13 C10 123.0(4) . .
C14 N13 H13 118.5 . .
C10 N13 H13 118.5 . .
C14 N15 H15A 120.0 . .
C14 N15 H15B 120.0 . .
H15A N15 H15B 120.0 . .
C14 N16 H16 120.0 . .
C14 N16 H16B 120.0 . .
H16 N16 H16B 120.0 . .
H1W O1W H2W 104(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.473(7) .
C2 C3 1.512(8) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N4 1.485(7) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C5 N4 1.505(7) .
C5 C6 1.511(7) .
C5 H5 0.9900 .
C5 H5B 0.9900 .
C6 N1 1.459(6) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 N12 1.355(6) .
C7 N1 1.361(6) .
C7 C8 1.405(7) .
C8 C9 1.361(7) .
C8 H8 0.9500 .
C9 C10 1.414(7) .
C9 H9 0.9500 .
C10 C11 1.351(7) .
C10 N13 1.440(6) .
C11 N12 1.364(6) .
C11 H11 0.9500 .
C14 N13 1.316(7) .
C14 N15 1.328(7) .
C14 N16 1.329(7) .
N4 H4A 0.9200 .
N4 H4B 0.9200 .
N12 H12 0.8800 .
N13 H13 0.8800 .
N15 H15A 0.8800 .
N15 H15B 0.8800 .
N16 H16 0.8800 .
N16 H16B 0.8800 .
O1W H1W 0.86(2) .
O1W H2W 0.85(2) .
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
N13 H13 Cl2 0.88 2.23 3.096(4) 167.3 .
N16 H16 Cl2 0.88 2.84 3.562(5) 140.1 .
N4 H4A Cl1 0.92 2.29 3.166(5) 158.9 2_456
N4 H4B Cl1 0.92 2.34 3.174(5) 151.3 1_444
N12 H12 Cl3 0.88 2.25 3.037(4) 148.9 1_455
N15 H15A Cl1 0.88 2.46 3.252(5) 149.5 2_566
O1W H1W Cl1 0.86(2) 2.46(3) 3.297(5) 168(6) 2_566
N15 H15B Cl3 0.88 2.33 3.140(5) 152.9 2_666
N16 H16B O1W 0.88 2.20 2.997(7) 150.1 2_666
N16 H16 Cl2 0.88 2.82 3.426(5) 127.3 2_667
O1W H2W Cl2 0.85(2) 2.32(4) 3.123(5) 156(7) 1_554
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045551
