#------------------------------------------------------------------------------
#$Date: 2025-08-20 22:19:29 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/51/4305187.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_4305187
loop_
_publ_author_name
'Christopher W. Belock'
'Anil Çetin'
'Natalie V. Barone'
'Christopher J. Ziegler'
_publ_section_title
;
Transition Metal Coordination Chemistry
of N,N-Bis(2-{pyrid-2-ylethyl})hydroxylamine
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7114
_journal_page_last               7120
_journal_paper_doi               10.1021/ic702406n
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C15 H23 Cl3 N3 O0.5'
_chemical_formula_weight         359.71
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.623(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2433(13)
_cell_length_b                   32.399(8)
_cell_length_c                   10.505(3)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      2.51
_cell_volume                     1768.8(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14656
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0625P)²+1.9499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                3051
_reflns_number_total             3853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic702406n-file002_8.cif
_cod_data_source_block           S3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1768.7(8)
_cod_original_formula_sum        'C15 H23 Cl3 N3 O0.50'
_cod_database_code               4305187
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1840(6) 0.96979(10) 0.5989(3) 0.0329(7) Uani 1 1 d . . .
H1 H 1.3127 0.9887 0.5805 0.040 Uiso 1 1 calc R . .
C2 C 1.0501(6) 0.97718(10) 0.6985(3) 0.0353(7) Uani 1 1 d . . .
H2 H 1.0837 1.0011 0.7506 0.042 Uiso 1 1 calc R . .
C3 C 0.8639(6) 0.94918(10) 0.7225(3) 0.0329(7) Uani 1 1 d . . .
H3 H 0.7667 0.9539 0.7912 0.039 Uiso 1 1 calc R . .
C4 C 0.8179(6) 0.91432(9) 0.6470(3) 0.0295(7) Uani 1 1 d . . .
H4 H 0.6905 0.8950 0.6642 0.035 Uiso 1 1 calc R . .
C5 C 0.9584(6) 0.90771(9) 0.5463(3) 0.0247(6) Uani 1 1 d . . .
C6 C 0.9220(7) 0.87165(9) 0.4565(3) 0.0314(7) Uani 1 1 d . . .
H6A H 0.7755 0.8773 0.3891 0.038 Uiso 1 1 calc R . .
H6B H 1.0781 0.8683 0.4138 0.038 Uiso 1 1 calc R . .
C7 C 0.8718(6) 0.83231(9) 0.5237(3) 0.0290(7) Uani 1 1 d . . .
H7A H 1.0091 0.8279 0.5967 0.035 Uiso 1 1 calc R . .
H7B H 0.7058 0.8345 0.5585 0.035 Uiso 1 1 calc R . .
C8 C 0.8780(6) 0.75642(9) 0.5044(3) 0.0252(6) Uani 1 1 d . . .
H8A H 0.7294 0.7538 0.5530 0.030 Uiso 1 1 calc R . .
H8B H 1.0374 0.7555 0.5665 0.030 Uiso 1 1 calc R . .
C9 C 0.8770(6) 0.72086(8) 0.4106(3) 0.0226(6) Uani 1 1 d . . .
H9A H 0.7230 0.7230 0.3454 0.027 Uiso 1 1 calc R . .
H9B H 1.0310 0.7228 0.3657 0.027 Uiso 1 1 calc R . .
C10 C 0.8762(5) 0.67977(9) 0.4768(2) 0.0211(6) Uani 1 1 d . . .
C11 C 0.7053(6) 0.66977(10) 0.5620(3) 0.0267(6) Uani 1 1 d . . .
H11 H 0.5837 0.6896 0.5826 0.032 Uiso 1 1 calc R . .
C12 C 0.7119(6) 0.63125(10) 0.6166(3) 0.0314(7) Uani 1 1 d . . .
H12 H 0.5938 0.6242 0.6743 0.038 Uiso 1 1 calc R . .
C13 C 0.8907(6) 0.60272(10) 0.5874(3) 0.0357(8) Uani 1 1 d . . .
H13 H 0.8993 0.5761 0.6259 0.043 Uiso 1 1 calc R . .
C14 C 1.0543(6) 0.61329(10) 0.5025(3) 0.0336(7) Uani 1 1 d . . .
H14 H 1.1770 0.5939 0.4805 0.040 Uiso 1 1 calc R . .
C15 C 0.2928(13) 0.9820(2) 0.0389(6) 0.099(2) Uani 1 1 d . . .
H15B H 0.3135 0.9811 0.1329 0.148 Uiso 1 1 calc R . .
H15A H 0.2755 0.9538 0.0048 0.148 Uiso 1 1 calc R . .
H16C H 0.1384 0.9979 0.0072 0.148 Uiso 1 1 calc R . .
Cl1 Cl 0.45280(15) 0.55668(2) 0.80816(7) 0.0306(2) Uani 1 1 d . . .
Cl2 Cl 0.31985(12) 0.79562(2) 0.27867(6) 0.02555(18) Uani 1 1 d . . .
Cl3 Cl 0.39895(15) 0.84357(3) 0.75113(8) 0.0423(3) Uani 1 1 d . . .
N1 N 1.1354(5) 0.93583(8) 0.5261(2) 0.0273(5) Uani 1 1 d . . .
H1A H 1.2246 0.9319 0.4618 0.033 Uiso 1 1 calc R . .
N2 N 0.8632(4) 0.79641(7) 0.4351(2) 0.0202(5) Uani 1 1 d . . .
H2A H 0.7128 0.7973 0.3790 0.024 Uiso 1 1 calc R . .
H2B H 0.9982 0.7982 0.3876 0.024 Uiso 1 1 calc R . .
N3 N 1.0426(4) 0.65120(7) 0.4496(2) 0.0246(5) Uani 1 1 d . . .
H3A H 1.1498 0.6573 0.3947 0.029 Uiso 1 1 calc R . .
O3 O 0.5000 1.0000 0.0000 0.129(3) Uani 1 2 d S . .
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 120.3(3) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 117.8(3) . . ?
N1 C5 C6 117.7(3) . . ?
C4 C5 C6 124.5(3) . . ?
C7 C6 C5 112.5(2) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C6 111.3(2) . . ?
N2 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 C9 110.5(2) . . ?
N2 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 111.9(2) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 C11 118.4(3) . . ?
N3 C10 C9 118.4(2) . . ?
C11 C10 C9 123.2(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N3 C14 C13 120.1(3) . . ?
N3 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
O3 C15 H16C 109.5 . . ?
H15B C15 H16C 109.5 . . ?
H15A C15 H16C 109.5 . . ?
C5 N1 C1 123.4(3) . . ?
C5 N1 H1A 118.3 . . ?
C1 N1 H1A 118.3 . . ?
C8 N2 C7 112.4(2) . . ?
C8 N2 H2A 109.1 . . ?
C7 N2 H2A 109.1 . . ?
C8 N2 H2B 109.1 . . ?
C7 N2 H2B 109.1 . . ?
H2A N2 H2B 107.9 . . ?
C10 N3 C14 122.8(3) . . ?
C10 N3 H3A 118.6 . . ?
C14 N3 H3A 118.6 . . ?
C15 O3 C15 180.000(4) 3_675 . ?
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
C1 N1 1.345(4) . ?
C1 C2 1.357(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.337(4) . ?
C5 C6 1.498(4) . ?
C6 C7 1.497(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.487(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.483(3) . ?
C8 C9 1.515(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.329(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.372(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.361(5) . ?
C13 H13 0.9500 . ?
C14 N3 1.346(4) . ?
C14 H14 0.9500 . ?
C15 O3 1.344(7) . ?
C15 H15B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H16C 0.9800 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N3 H3A 0.8800 . ?
O3 C15 1.344(7) 3_675 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139128006
