#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/30/7213090.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213090
loop_
_publ_author_name
'Long, Nicholas J.'
'Parker, David G.'
'Speyer, Paul R.'
'White, Andrew J. P.'
'Williams, David J.'
_publ_section_title
;
 Efficient syntheses of polymerisable pendant arm azamacrocycles and
 formation of poly(vinylbenzyltriazacyclododecane)
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1621
_journal_paper_doi               10.1039/a903318a
_journal_year                    1999
_chemical_formula_sum            'C18 H30 N4 O3'
_chemical_formula_weight         350.46
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.215(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.382(2)
_cell_length_b                   12.1345(12)
_cell_length_c                   17.121(2)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.49
_cell_measurement_theta_min      5.22
_cell_volume                     1933.7(5)
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3630
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        7.11
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       blocks
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0056(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.009
_refine_ls_goodness_of_fit_obs   1.097
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_restrained_S_obs      1.096
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_obs          0.0520
_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)+(0.0601P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1463
_refine_ls_wR_factor_obs         0.1213
_reflns_number_observed          2203
_reflns_number_total             3408
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            903318asup1.cif
_cod_data_source_block           NL9804
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.0000P] 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^)+(0.0601P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7213090
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.3594(2) 0.0981(2) 0.19536(12) 0.0520(5) Uani 1 d .
C2 C 0.4167(3) 0.0337(3) 0.2651(2) 0.0695(8) Uani 1 d .
H2A H 0.5110(3) 0.0622(3) 0.2848(2) 0.083 Uiso 1 calc R
H2B H 0.4289(3) -0.0420(3) 0.2491(2) 0.083 Uiso 1 calc R
C3 C 0.3243(4) 0.0344(3) 0.3320(2) 0.0755(9) Uani 1 d .
H3A H 0.3679(4) -0.0143(3) 0.3732(2) 0.091 Uiso 1 calc R
H3B H 0.3252(4) 0.1082(3) 0.3538(2) 0.091 Uiso 1 calc R
C4 C 0.1693(4) -0.0005(2) 0.3097(2) 0.0735(9) Uani 1 d .
H4A H 0.1653(4) -0.0623(2) 0.2736(2) 0.088 Uiso 1 calc R
H4B H 0.1290(4) -0.0239(2) 0.3565(2) 0.088 Uiso 1 calc R
N5 N 0.0853(3) 0.0908(2) 0.27281(12) 0.0598(6) Uani 1 d D
H5A H 0.0927(39) 0.1494(17) 0.3053(16) 0.084(11) Uiso 1 d D
C6 C -0.0686(3) 0.0697(3) 0.2525(2) 0.0703(8) Uani 1 d .
H6A H -0.1147(3) 0.0648(3) 0.3000(2) 0.084 Uiso 1 calc R
H6B H -0.0830(3) 0.0004(3) 0.2243(2) 0.084 Uiso 1 calc R
C7 C -0.1331(3) 0.1629(3) 0.2015(2) 0.0724(8) Uani 1 d .
H7A H -0.1094(3) 0.2321(3) 0.2285(2) 0.087 Uiso 1 calc R
H7B H -0.2369(3) 0.1555(3) 0.1949(2) 0.087 Uiso 1 calc R
C8 C -0.0824(3) 0.1675(3) 0.1211(2) 0.0692(7) Uani 1 d .
H8A H -0.1134(3) 0.1012(3) 0.0922(2) 0.083 Uiso 1 calc R
H8B H -0.1272(3) 0.2299(3) 0.0923(2) 0.083 Uiso 1 calc R
N9 N 0.0768(2) 0.1776(2) 0.12491(11) 0.0507(5) Uani 1 d D
H9A H 0.1022(28) 0.1578(21) 0.0779(7) 0.051(7) Uiso 1 d D
H9B H 0.1196(32) 0.1311(22) 0.1616(14) 0.079(10) Uiso 1 d D
C10 C 0.1369(3) 0.2878(2) 0.14774(15) 0.0562(6) Uani 1 d .
H10A H 0.1125(3) 0.3067(2) 0.19948(15) 0.067 Uiso 1 calc R
H10B H 0.0935(3) 0.3423(2) 0.11073(15) 0.067 Uiso 1 calc R
C11 C 0.2971(3) 0.2915(2) 0.1492(2) 0.0619(7) Uani 1 d .
H11A H 0.3290(3) 0.3668(2) 0.1592(2) 0.074 Uiso 1 calc R
H11B H 0.3205(3) 0.2711(2) 0.0976(2) 0.074 Uiso 1 calc R
C12 C 0.3807(3) 0.2169(2) 0.2103(2) 0.0625(7) Uani 1 d .
H12A H 0.4822(3) 0.2335(2) 0.2123(2) 0.075 Uiso 1 calc R
H12B H 0.3526(3) 0.2339(2) 0.2616(2) 0.075 Uiso 1 calc R
C13 C 0.4271(3) 0.0643(2) 0.1265(2) 0.0634(7) Uani 1 d .
H13A H 0.5301(3) 0.0754(2) 0.1376(2) 0.076 Uiso 1 calc R
H13B H 0.3920(3) 0.1111(2) 0.0823(2) 0.076 Uiso 1 calc R
C14 C 0.3985(3) -0.0550(2) 0.10334(14) 0.0527(6) Uani 1 d .
C15 C 0.5062(3) -0.1184(2) 0.0787(2) 0.0619(6) Uani 1 d .
H15A H 0.5969(3) -0.0880(2) 0.0773(2) 0.074 Uiso 1 calc R
C16 C 0.4808(3) -0.2269(2) 0.0559(2) 0.0659(7) Uani 1 d .
H16A H 0.5546(3) -0.2677(2) 0.0385(2) 0.079 Uiso 1 calc R
C17 C 0.3484(3) -0.2762(2) 0.05856(13) 0.0566(6) Uani 1 d .
C18 C 0.2407(3) -0.2129(2) 0.0841(2) 0.0622(7) Uani 1 d .
H18A H 0.1510(3) -0.2441(2) 0.0871(2) 0.075 Uiso 1 calc R
C19 C 0.2650(3) -0.1034(2) 0.1052(2) 0.0611(7) Uani 1 d .
H19A H 0.1904(3) -0.0617(2) 0.1209(2) 0.073 Uiso 1 calc R
C20 C 0.3245(4) -0.3921(2) 0.0345(2) 0.0730(9) Uani 1 d .
H20A H 0.4049(4) -0.4304(2) 0.0228(2) 0.088 Uiso 1 calc R
C21 C 0.2051(5) -0.4470(3) 0.0278(2) 0.0845(10) Uani 1 d .
H21A H 0.1210(5) -0.4130(3) 0.0388(2) 0.101 Uiso 1 calc R
H21B H 0.2035(5) -0.5204(3) 0.0120(2) 0.101 Uiso 1 calc R
N N -0.1266(2) -0.1869(2) 0.07425(12) 0.0548(5) Uani 1 d .
O1 O -0.1182(3) -0.1758(2) 0.14582(11) 0.0878(7) Uani 1 d .
O2 O -0.1339(3) -0.1051(2) 0.03043(12) 0.0782(6) Uani 1 d .
O3 O -0.1274(3) -0.2800(2) 0.04530(13) 0.0809(7) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 N1 C2 110.7(2)
C13 N1 C12 110.5(2)
C2 N1 C12 110.6(2)
N1 C2 C3 115.1(2)
C4 C3 C2 115.4(2)
N5 C4 C3 110.3(2)
C4 N5 C6 115.7(2)
N5 C6 C7 108.6(2)
C6 C7 C8 113.8(3)
N9 C8 C7 113.0(2)
C10 N9 C8 115.5(2)
N9 C10 C11 112.2(2)
C10 C11 C12 115.0(2)
N1 C12 C11 114.5(2)
N1 C13 C14 113.4(2)
C15 C14 C19 118.0(2)
C15 C14 C13 120.0(3)
C19 C14 C13 121.9(2)
C14 C15 C16 120.6(3)
C17 C16 C15 121.6(3)
C18 C17 C16 117.7(3)
C18 C17 C20 121.8(3)
C16 C17 C20 120.5(3)
C17 C18 C19 120.8(3)
C14 C19 C18 121.2(2)
C21 C20 C17 127.9(3)
O1 N O3 119.9(2)
O1 N O2 120.6(2)
O3 N O2 119.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.467(3)
N1 C2 1.472(3)
N1 C12 1.473(3)
C2 C3 1.520(5)
C3 C4 1.517(5)
C4 N5 1.457(4)
N5 C6 1.465(4)
C6 C7 1.508(5)
C7 C8 1.514(4)
C8 N9 1.492(4)
N9 C10 1.484(3)
C10 C11 1.500(4)
C11 C12 1.524(4)
C13 C14 1.516(4)
C14 C15 1.378(4)
C14 C19 1.387(4)
C15 C16 1.385(4)
C16 C17 1.385(4)
C17 C18 1.382(4)
C17 C20 1.474(4)
C18 C19 1.389(4)
C20 C21 1.297(5)
N O1 1.225(3)
N O3 1.234(3)
N O2 1.240(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10689225
