#------------------------------------------------------------------------------
#$Date: 2016-03-25 22:53:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180018 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/12/7031253.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_7031253
loop_
_publ_author_name
'Breedlove, B. K.'
'Kandel, R.'
'Ahsan, H. Md'
'Yamashita, M.'
_publ_section_title
;
 4-Pyridyl-substituted azacycloalkanes with multiple donor sites prepared
 via a solvent-free, one-pot method for use in electrocatalysts.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7683
_journal_page_last               7686
_journal_paper_doi               10.1039/c4dt00240g
_journal_volume                  43
_journal_year                    2014
_chemical_formula_sum            'C21 H24 N6 O'
_chemical_formula_weight         376.46
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-03-07 # Formatted by publCIF

;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   10.277(5)
_cell_length_b                   14.718(5)
_cell_length_c                   25.634(5)
_cell_measurement_reflns_used    9003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.54
_cell_volume                     3877(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'Mercury 3.3'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20253
_diffrn_reflns_theta_full        22.37
_diffrn_reflns_theta_max         22.37
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0264
_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)+(0.0396P)²+1.0860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0694
_reflns_number_gt                2150
_reflns_number_total             2491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt00240g2.cif
_cod_data_source_block           py3tacn_1_0m
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7031253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
H1 H 0.2594(15) 0.4247(9) 0.1562(5) 0.023(4) Uiso 1 1 d
H2 H 0.3600(13) 0.5058(11) 0.1514(5) 0.021(4) Uiso 1 1 d
H3 H 0.3227(14) 0.4355(9) 0.0689(5) 0.019(4) Uiso 1 1 d
H4 H 0.3796(13) 0.3427(11) 0.0909(5) 0.019(4) Uiso 1 1 d
H5 H 0.6795(14) 0.3736(9) 0.0478(5) 0.015(3) Uiso 1 1 d
H6 H 0.5651(13) 0.3027(9) 0.0574(5) 0.015(3) Uiso 1 1 d
H7 H 0.7377(14) 0.2781(9) 0.1166(5) 0.020(4) Uiso 1 1 d
H8 H 0.6035(14) 0.2985(9) 0.1457(5) 0.017(4) Uiso 1 1 d
H9 H 0.7337(14) 0.4504(9) 0.2268(5) 0.021(4) Uiso 1 1 d
H10 H 0.6728(13) 0.3516(10) 0.2239(5) 0.020(4) Uiso 1 1 d
N1 N 0.43261(10) 0.40028(7) 0.19006(4) 0.0186(3) Uani 1 1 d
H11 H 0.5224(13) 0.4691(9) 0.2479(6) 0.018(3) Uiso 1 1 d
H12 H 0.5380(13) 0.5140(10) 0.1908(6) 0.025(4) Uiso 1 1 d
H13 H 0.2022(16) 0.1455(11) 0.1994(6) 0.041(5) Uiso 1 1 d
H14 H 0.2645(14) 0.2766(10) 0.1560(6) 0.028(4) Uiso 1 1 d
H15 H 0.5088(15) 0.3295(10) 0.2812(6) 0.027(4) Uiso 1 1 d
H16 H 0.4346(13) 0.1979(10) 0.3179(6) 0.022(4) Uiso 1 1 d
H17 H 0.7864(15) 0.6531(9) 0.0228(5) 0.019(4) Uiso 1 1 d
H18 H 0.7462(15) 0.5040(10) 0.0441(5) 0.022(4) Uiso 1 1 d
H19 H 0.3679(16) 0.5785(9) 0.0749(5) 0.021(4) Uiso 1 1 d
C1 C 0.35253(15) 0.43895(10) 0.14862(6) 0.0216(3) Uani 1 1 d
H20 H 0.4258(14) 0.7245(10) 0.0540(5) 0.022(4) Uiso 1 1 d
H21 H 1.0114(15) 0.6270(11) 0.1523(6) 0.033(4) Uiso 1 1 d
H22 H 0.8278(14) 0.5558(10) 0.1863(6) 0.028(4) Uiso 1 1 d
H23 H 0.8947(14) 0.3500(11) 0.0815(5) 0.024(4) Uiso 1 1 d
H24 H 1.0721(15) 0.4329(10) 0.0500(6) 0.032(4) Uiso 1 1 d
H25 H 0.377(2) 0.1377(15) 0.0627(8) 0.073(6) Uiso 1 1 d
H26 H 0.355(2) 0.2093(14) 0.0223(9) 0.070(7) Uiso 1 1 d
C2 C 0.38723(14) 0.40813(10) 0.09364(6) 0.0211(3) Uani 1 1 d
N2 N 0.51915(11) 0.43124(7) 0.07717(4) 0.0189(3) Uani 1 1 d
C3 C 0.61169(15) 0.35635(10) 0.07232(6) 0.0200(3) Uani 1 1 d
C4 C 0.67100(14) 0.32533(9) 0.12401(6) 0.0188(3) Uani 1 1 d
N3 N 0.72546(10) 0.40009(7) 0.15454(4) 0.0182(3) Uani 1 1 d
C5 C 0.67359(14) 0.41229(11) 0.20708(6) 0.0217(3) Uani 1 1 d
C6 C 0.53944(14) 0.45548(10) 0.21085(6) 0.0213(3) Uani 1 1 d
N4 N 0.31248(14) 0.15712(9) 0.26280(6) 0.0407(4) Uani 1 1 d
C7 C 0.26650(16) 0.18371(10) 0.21648(7) 0.0328(4) Uani 1 1 d
C8 C 0.30325(14) 0.26204(10) 0.19036(6) 0.0259(4) Uani 1 1 d
C9 C 0.39586(13) 0.32045(9) 0.21330(5) 0.0207(3) Uani 1 1 d
C10 C 0.44615(14) 0.29180(10) 0.26172(6) 0.0263(4) Uani 1 1 d
C11 C 0.40139(16) 0.21283(11) 0.28411(7) 0.0356(4) Uani 1 1 d
N5 N 0.60987(13) 0.70283(8) 0.03686(5) 0.0285(3) Uani 1 1 d
C12 C 0.69798(16) 0.63544(10) 0.03488(6) 0.0258(4) Uani 1 1 d
C13 C 0.67460(15) 0.54621(10) 0.04728(5) 0.0223(4) Uani 1 1 d
C14 C 0.54978(14) 0.51907(9) 0.06409(5) 0.0200(3) Uani 1 1 d
C15 C 0.45659(16) 0.58917(10) 0.06601(6) 0.0232(4) Uani 1 1 d
C16 C 0.49096(16) 0.67657(10) 0.05253(6) 0.0264(4) Uani 1 1 d
N6 N 1.05812(12) 0.53743(8) 0.09892(5) 0.0293(3) Uani 1 1 d
C17 C 0.98554(15) 0.56875(10) 0.13879(6) 0.0265(4) Uani 1 1 d
C18 C 0.87852(14) 0.52605(10) 0.15961(6) 0.0223(3) Uani 1 1 d
C19 C 0.83711(13) 0.44276(9) 0.13838(5) 0.0185(3) Uani 1 1 d
C20 C 0.91445(14) 0.40780(10) 0.09760(6) 0.0220(4) Uani 1 1 d
C21 C 1.01965(14) 0.45672(10) 0.08004(6) 0.0254(4) Uani 1 1 d
O1 O 0.32294(11) 0.19486(8) 0.05576(5) 0.0378(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C1 119.70(12)
C9 N1 C6 121.56(12)
C1 N1 C6 118.09(12)
N1 C1 C2 115.17(12)
N2 C2 C1 114.56(12)
C14 N2 C2 120.21(11)
C14 N2 C3 122.72(12)
C2 N2 C3 116.95(11)
N2 C3 C4 114.27(11)
N3 C4 C3 113.08(11)
C19 N3 C5 121.85(11)
C19 N3 C4 120.21(11)
C5 N3 C4 116.54(11)
N3 C5 C6 116.16(12)
N1 C6 C5 115.09(12)
C7 N4 C11 115.02(14)
N4 C7 C8 125.20(16)
C7 C8 C9 119.31(16)
N1 C9 C10 122.58(13)
N1 C9 C8 121.81(13)
C10 C9 C8 115.61(14)
C11 C10 C9 119.85(16)
N4 C11 C10 124.99(17)
C16 N5 C12 114.32(13)
N5 C12 C13 125.42(16)
C12 C13 C14 120.05(14)
N2 C14 C15 121.70(13)
N2 C14 C13 123.36(12)
C15 C14 C13 114.93(13)
C16 C15 C14 120.04(15)
N5 C16 C15 125.23(15)
C21 N6 C17 114.43(13)
N6 C17 C18 125.54(14)
C17 C18 C19 119.35(14)
N3 C19 C18 122.34(13)
N3 C19 C20 121.87(13)
C18 C19 C20 115.73(13)
C21 C20 C19 119.65(14)
N6 C21 C20 125.25(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.3705(18)
N1 C1 1.4593(18)
N1 C6 1.4661(18)
C1 C2 1.523(2)
C2 N2 1.4601(19)
N2 C14 1.3721(18)
N2 C3 1.4612(18)
C3 C4 1.528(2)
C4 N3 1.4615(18)
N3 C19 1.3720(18)
N3 C5 1.4597(18)
C5 C6 1.521(2)
N4 C7 1.337(2)
N4 C11 1.344(2)
C7 C8 1.386(2)
C8 C9 1.411(2)
C9 C10 1.409(2)
C10 C11 1.375(2)
N5 C16 1.343(2)
N5 C12 1.344(2)
C12 C13 1.372(2)
C13 C14 1.411(2)
C14 C15 1.409(2)
C15 C16 1.378(2)
N6 C21 1.342(2)
N6 C17 1.347(2)
C17 C18 1.375(2)
C18 C19 1.407(2)
C19 C20 1.410(2)
C20 C21 1.375(2)
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
C9 N1 C1 C2 -90.06(16)
C6 N1 C1 C2 99.07(15)
N1 C1 C2 N2 -60.99(17)
C1 C2 N2 C14 -74.52(16)
C1 C2 N2 C3 109.27(14)
C14 N2 C3 C4 103.55(15)
C2 N2 C3 C4 -80.35(15)
N2 C3 C4 N3 -51.20(17)
C3 C4 N3 C19 -70.75(16)
C3 C4 N3 C5 122.53(13)
C19 N3 C5 C6 117.60(14)
C4 N3 C5 C6 -75.92(16)
C9 N1 C6 C5 66.89(17)
C1 N1 C6 C5 -122.42(14)
N3 C5 C6 N1 67.05(17)
C11 N4 C7 C8 -0.2(2)
N4 C7 C8 C9 -0.3(2)
C1 N1 C9 C10 -162.47(13)
C6 N1 C9 C10 8.08(19)
C1 N1 C9 C8 16.64(19)
C6 N1 C9 C8 -172.81(12)
C7 C8 C9 N1 -177.81(13)
C7 C8 C9 C10 1.35(19)
N1 C9 C10 C11 177.27(13)
C8 C9 C10 C11 -1.9(2)
C7 N4 C11 C10 -0.4(2)
C9 C10 C11 N4 1.5(2)
C16 N5 C12 C13 0.0(2)
N5 C12 C13 C14 -0.5(2)
C2 N2 C14 C15 0.00(19)
C3 N2 C14 C15 175.98(12)
C2 N2 C14 C13 -179.25(12)
C3 N2 C14 C13 -3.3(2)
C12 C13 C14 N2 -179.95(13)
C12 C13 C14 C15 0.75(19)
N2 C14 C15 C16 -179.94(13)
C13 C14 C15 C16 -0.63(19)
C12 N5 C16 C15 0.1(2)
C14 C15 C16 N5 0.2(2)
C21 N6 C17 C18 -1.2(2)
N6 C17 C18 C19 -0.6(2)
C5 N3 C19 C18 -27.64(19)
C4 N3 C19 C18 166.36(12)
C5 N3 C19 C20 155.42(13)
C4 N3 C19 C20 -10.58(19)
C17 C18 C19 N3 -174.80(13)
C17 C18 C19 C20 2.32(19)
N3 C19 C20 C21 174.83(13)
C18 C19 C20 C21 -2.30(19)
C17 N6 C21 C20 1.2(2)
C19 C20 C21 N6 0.5(2)
