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#$Date: 2025-08-21 13:21:36 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301847 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/11/7011161.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_7011161
loop_
_publ_author_name
'Long, Nicholas J.'
'Parker, David G.'
'Speyer, Paul R.'
'White, Andrew J. P.'
'Williams, David J.'
_publ_section_title
;
 Synthesis, characterisation and polymerisation of
 vinylbenzene-substituted triazacyclododecanes and their transition
 metal complexes
;
_journal_issue                   10
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2142
_journal_paper_doi               10.1039/b108235n
_journal_year                    2002
_chemical_formula_sum            'C19 H30 Cl N3 O'
_chemical_formula_weight         351.91
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.868(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5465(4)
_cell_length_b                   12.7121(7)
_cell_length_c                   14.9812(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      11.13
_cell_volume                     1958.06(16)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3299
_diffrn_reflns_theta_max         62.98
_diffrn_reflns_theta_min         4.61
_diffrn_standards_decay_%        2.37
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.796
_exptl_absorpt_correction_T_max  0.8425
_exptl_absorpt_correction_T_min  0.5038
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       'Prismatic needles'
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.93
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0092(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.084
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.061
_refine_ls_restrained_S_obs      1.086
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_obs          0.0457
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+0.5968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1203
_refine_ls_wR_factor_obs         0.1106
_reflns_number_observed          2548
_reflns_number_total             3116
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b108235n.txt
_cod_data_source_block           NL9703
_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.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5968P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+0.5968P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1958.1(2)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7011161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.7263(2) 0.23647(12) 0.40697(11) 0.0462(4) Uani 1 d . .
C2 C 0.7498(2) 0.3030(2) 0.4891(2) 0.0572(6) Uani 1 d . .
H2A H 0.8312(2) 0.3403(2) 0.4938(2) 0.069 Uiso 1 calc R .
H2B H 0.7586(2) 0.2584(2) 0.5427(2) 0.069 Uiso 1 calc R .
C3 C 0.6415(2) 0.3829(2) 0.4889(2) 0.0666(7) Uani 1 d . .
H3A H 0.5588(2) 0.3462(2) 0.4756(2) 0.080 Uiso 1 calc R .
H3B H 0.6533(2) 0.4125(2) 0.5499(2) 0.080 Uiso 1 calc R .
C4 C 0.6350(3) 0.4724(2) 0.4210(2) 0.0658(6) Uani 1 d . .
H4A H 0.5666(3) 0.5206(2) 0.4280(2) 0.079 Uiso 1 calc R .
H4B H 0.7166(3) 0.5106(2) 0.4350(2) 0.079 Uiso 1 calc R .
N5 N 0.6099(2) 0.43662(13) 0.32545(13) 0.0515(4) Uani 1 d . .
C6 C 0.4773(2) 0.4142(2) 0.2773(2) 0.0685(7) Uani 1 d . .
H6A H 0.4224(2) 0.4745(2) 0.2810(2) 0.082 Uiso 1 calc R .
H6B H 0.4441(2) 0.3547(2) 0.3056(2) 0.082 Uiso 1 calc R .
C7 C 0.4743(3) 0.3896(2) 0.1783(2) 0.0768(8) Uani 1 d . .
H7A H 0.3878(3) 0.3663(2) 0.1480(2) 0.092 Uiso 1 calc R .
H7B H 0.4942(3) 0.4527(2) 0.1476(2) 0.092 Uiso 1 calc R .
C8 C 0.5714(2) 0.3052(2) 0.1715(2) 0.0669(6) Uani 1 d . .
H8A H 0.5456(2) 0.2395(2) 0.1952(2) 0.080 Uiso 1 calc R .
H8B H 0.5747(2) 0.2946(2) 0.1080(2) 0.080 Uiso 1 calc R .
N9 N 0.6995(2) 0.33691(13) 0.22446(13) 0.0543(5) Uani 1 d . .
C10 C 0.8138(3) 0.2735(2) 0.2195(2) 0.0657(6) Uani 1 d . .
H10A H 0.8913(3) 0.3164(2) 0.2379(2) 0.079 Uiso 1 calc R .
H10B H 0.8076(3) 0.2519(2) 0.1566(2) 0.079 Uiso 1 calc R .
C11 C 0.8274(2) 0.1757(2) 0.2804(2) 0.0609(6) Uani 1 d . .
H11A H 0.7503(2) 0.1326(2) 0.2609(2) 0.073 Uiso 1 calc R .
H11B H 0.9012(2) 0.1351(2) 0.2711(2) 0.073 Uiso 1 calc R .
C12 C 0.8456(2) 0.1981(2) 0.3826(2) 0.0546(5) Uani 1 d . .
H12A H 0.8737(2) 0.1342(2) 0.4167(2) 0.066 Uiso 1 calc R .
H12B H 0.9136(2) 0.2503(2) 0.4006(2) 0.066 Uiso 1 calc R .
C13 C 0.7080(2) 0.39504(15) 0.29779(15) 0.0495(5) Uani 1 d . .
H13A H 0.7908(2) 0.40785(15) 0.33321(15) 0.059 Uiso 1 calc R .
C14 C 0.6273(2) 0.1539(2) 0.40620(14) 0.0500(5) Uani 1 d . .
H14A H 0.6109(2) 0.1190(2) 0.34714(14) 0.060 Uiso 1 calc R .
H14B H 0.5469(2) 0.1877(2) 0.41174(14) 0.060 Uiso 1 calc R .
C15 C 0.6609(2) 0.0708(2) 0.48006(14) 0.0487(5) Uani 1 d . .
C16 C 0.7285(2) -0.0194(2) 0.4676(2) 0.0613(6) Uani 1 d . .
H16A H 0.7541(2) -0.0293(2) 0.4126(2) 0.074 Uiso 1 calc R .
C17 C 0.7587(3) -0.0951(2) 0.5354(2) 0.0730(7) Uani 1 d . .
H17A H 0.8048(3) -0.1548(2) 0.5254(2) 0.088 Uiso 1 calc R .
C18 C 0.7214(3) -0.0834(2) 0.6176(2) 0.0712(7) Uani 1 d D .
C19 C 0.6516(2) 0.0055(2) 0.6298(2) 0.0673(7) Uani 1 d . .
H19A H 0.6243(2) 0.0146(2) 0.6842(2) 0.081 Uiso 1 calc R .
C20 C 0.6221(2) 0.0809(2) 0.56226(15) 0.0561(5) Uani 1 d . .
H20A H 0.5750(2) 0.1400(2) 0.57201(15) 0.067 Uiso 1 calc R .
C21 C 0.7418(4) -0.1529(4) 0.6982(3) 0.0652(11) Uani 0.62 d PD 1
H21A H 0.7073(4) -0.1331(4) 0.7477(3) 0.078 Uiso 0.62 calc PR 1
C22 C 0.8064(5) -0.2414(4) 0.7029(4) 0.094(2) Uani 0.62 d PD 1
H22A H 0.8416(5) -0.2624(4) 0.6540(4) 0.113 Uiso 0.62 calc PR 1
H22B H 0.8172(5) -0.2831(4) 0.7550(4) 0.113 Uiso 0.62 calc PR 1
C21' C 0.7778(9) -0.1862(7) 0.6713(6) 0.069(2) Uiso 0.38 d PD 2
H21B H 0.8200(9) -0.2388(7) 0.6460(6) 0.082 Uiso 0.38 calc PR 2
C22' C 0.7595(9) -0.1902(7) 0.7543(6) 0.086(2) Uiso 0.38 d PD 2
H22C H 0.7167(9) -0.1356(7) 0.7766(6) 0.104 Uiso 0.38 calc PR 2
H22D H 0.7893(9) -0.2478(7) 0.7914(6) 0.104 Uiso 0.38 calc PR 2
Cl Cl 0.01103(7) 0.51355(5) 0.33959(4) 0.0725(3) Uani 1 d . .
O30 O 0.1080(2) 0.3636(2) 0.5103(2) 0.0838(6) Uani 1 d D .
H30A H 0.0741(31) 0.3981(24) 0.5520(18) 0.112(13) Uiso 1 d D .
H30B H 0.0892(42) 0.4049(27) 0.4603(17) 0.154(17) Uiso 1 d D .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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
C2 N1 C12 113.9(2) . . ?
C2 N1 C14 113.7(2) . . ?
C12 N1 C14 113.9(2) . . ?
N1 C2 C3 113.3(2) . . ?
C4 C3 C2 115.0(2) . . ?
N5 C4 C3 113.2(2) . . ?
C13 N5 C6 120.3(2) . . ?
C13 N5 C4 116.8(2) . . ?
C6 N5 C4 119.3(2) . . ?
N5 C6 C7 109.7(2) . . ?
C8 C7 C6 110.4(2) . . ?
N9 C8 C7 109.1(2) . . ?
C13 N9 C8 119.5(2) . . ?
C13 N9 C10 116.7(2) . . ?
C8 N9 C10 119.5(2) . . ?
N9 C10 C11 112.7(2) . . ?
C12 C11 C10 114.8(2) . . ?
N1 C12 C11 112.8(2) . . ?
N5 C13 N9 125.6(2) . . ?
N1 C14 C15 116.1(2) . . ?
C16 C15 C20 117.3(2) . . ?
C16 C15 C14 121.5(2) . . ?
C20 C15 C14 121.2(2) . . ?
C17 C16 C15 121.2(2) . . ?
C18 C17 C16 120.9(3) . . ?
C17 C18 C19 118.1(2) . . ?
C17 C18 C21 130.4(3) . . ?
C19 C18 C21 111.5(3) . . ?
C17 C18 C21' 102.4(4) . . ?
C19 C18 C21' 139.5(4) . . ?
C20 C19 C18 120.7(2) . . ?
C19 C20 C15 121.7(2) . . ?
C22 C21 C18 122.5(5) . . ?
C22' C21' C18 113.6(9) . . ?
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
N1 C2 1.467(3) . ?
N1 C12 1.469(3) . ?
N1 C14 1.479(2) . ?
C2 C3 1.528(3) . ?
C3 C4 1.517(4) . ?
C4 N5 1.468(3) . ?
N5 C13 1.309(3) . ?
N5 C6 1.452(3) . ?
C6 C7 1.509(4) . ?
C7 C8 1.503(3) . ?
C8 N9 1.463(3) . ?
N9 C13 1.310(3) . ?
N9 C10 1.466(3) . ?
C10 C11 1.530(3) . ?
C11 C12 1.527(3) . ?
C14 C15 1.513(3) . ?
C15 C16 1.385(3) . ?
C15 C20 1.387(3) . ?
C16 C17 1.384(3) . ?
C17 C18 1.383(4) . ?
C18 C19 1.383(4) . ?
C18 C21 1.472(4) . ?
C18 C21' 1.579(9) . ?
C19 C20 1.378(3) . ?
C21 C22 1.309(7) . ?
C21' C22' 1.301(11) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139154476
