#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2003517.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2003517
loop_
_publ_author_name
'Tahirov, T. H.'
'Lu, T.-H.'
'Liu, G.-S.'
'Chi, T.-Y.'
'Chung, C.-S.'
_publ_section_title
;
 Two Isomers of 5,7,12,14-Tetramethyl-1,4,8,11-tetraazacyclotetradecane
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1146
_journal_page_last               1148
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C14 H32 N4,2H2 O1'
_chemical_formula_sum            'C14 H36 N4 O2'
_chemical_formula_weight         292.46
_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_type_scat_source           IntTabIV
_cell_angle_alpha                110.10(2)
_cell_angle_beta                 103.800(10)
_cell_angle_gamma                91.465(9)
_cell_formula_units_Z            3
_cell_length_a                   8.6917(7)
_cell_length_b                   11.5760(10)
_cell_length_c                   15.006(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(3)
_cell_measurement_theta_max      15.04
_cell_measurement_theta_min      7.42
_cell_volume                     1367.3(4)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.008
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3860
_diffrn_reflns_theta_max         22.5
_diffrn_standards_decay_%        14
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.8178
_exptl_absorpt_correction_type
'empirical (North, Phillips & Matthews, 1968)'
_exptl_crystal_colour            'transparent, colorless'
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_description       cuboid
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.28(4)
_refine_diff_density_min         -0.11(4)
_refine_ls_extinction_coef       '1.2(2) (length in mm)'
_refine_ls_extinction_method     'Zachariasen (1968)'
_refine_ls_goodness_of_fit_obs   1.21
_refine_ls_number_parameters     488
_refine_ls_number_reflns         2688
_refine_ls_R_factor_obs          0.051
_refine_ls_shift/esd_max         0.251
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 1/[\s(F~o~)^2^ + 0.002F~o~^2^]'
_refine_ls_wR_factor_obs         0.068
_reflns_number_observed          2688
_reflns_number_total             3572
_reflns_observed_criterion       I>=\s(I)
_[local]_cod_data_source_file    as1126.cif
_[local]_cod_data_source_block   as1126a
_cod_original_cell_volume        1367.3(3)
_cod_database_code               2003517
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
O(W1) .4984(10) .4259(9) .2579(7) 0.50
O(W1') .5805(9) .4121(9) .2732(7) 0.50
O(W2) .8607(8) .4559(6) .2126(6) 0.55
O(W2') .8470(14) .4617(10) .2746(9) 0.30
O(W2") .942(3) .462(3) .254(4) 0.15
O(W3) .3003(10) .5315(6) .2989(5) 0.50
O(W3') .1933(7) .5335(6) .2900(5) 0.50
N(1) .0222(3) .3246(2) .39019(16) 1.00
N(2) -.3051(3) .2442(2) .37760(16) 1.00
N(3) -.2010(3) .2166(2) .57267(16) 1.00
N(4) .1296(3) .2999(2) .58722(16) 1.00
N(5) .6941(3) .39217(19) .00204(16) 1.00
N(6) .3792(2) .37867(19) .04593(16) 1.00
C(1) .1244(5) .1981(5) .2512(3) 1.00
C(2) .0159(3) .2005(3) .3175(2) 1.00
C(3) -.1553(4) .1535(3) .2565(2) 1.00
C(4) -.2752(4) .1274(3) .3084(2) 1.00
C(5) -.4281(5) .0553(4) .2327(3) 1.00
C(6) -.4112(4) .2322(4) .4369(3) 1.00
C(7) -.3544(4) .1582(3) .5021(2) 1.00
C(8) -.1245(4) .1403(3) .6266(2) 1.00
C(9) -.2280(6) .1120(5) .6876(3) 1.00
C(10) .0388(4) .2031(3) .6907(2) 1.00
C(11) .1671(4) .2143(3) .6397(2) 1.00
C(12) .3309(5) .2543(5) .7133(3) 1.00
C(13) .2375(4) .3057(4) .5275(2) 1.00
C(14) .1771(4) .3780(3) .4616(2) 1.00
C(15) .8121(4) .1944(3) -.0294(3) 1.00
C(16) .6606(3) .2563(2) -.0365(2) 1.00
C(18) .3818(3) .2457(2) -.0030(2) 1.00
C(17) .5537(3) .2153(3) .0162(2) 1.00
C(19) .2791(4) .1679(4) .0291(3) 1.00
C(20) .7785(3) .5795(3) -.0241(3) 1.00
C(21) .7667(4) .4406(3) -.0583(3) 1.00
H(N1) -.004 .382 .358 0.5
H(N1') -.065 .336 .425 0.5
H(N2) -.207 .299 .422 0.5
H(N2') -.350 .306 .329 0.5
H(N3) -.126 .227 .532 0.5
H(N3') -.212 .298 .625 0.5
H(N4) .008 .286 .557 0.5
H(N4') .129 .384 .633 0.5
H(N5) .750 .428 .075 0.5
H(N5') .591 .428 .016 0.5
H(N6) .457 .423 .032 0.5
H(N6') .432 .407 .118 0.5
H(1) .114(4) .118(3) .203(3) 1.0
H(2) .090(5) .261(4) .212(3) 1.0
H(3) .240(5) .230(4) .286(3) 1.0
H(4) .053(3) .143(3) .3540(19) 1.0
H(5) -.201(3) .214(2) .2227(19) 1.0
H(6) -.154(4) .075(3) .201(2) 1.0
H(7) -.227(3) .074(3) .3475(19) 1.0
H(8) -.504(4) .032(3) .263(3) 1.0
H(9) -.483(5) .116(4) .197(3) 1.0
H(10) -.406(4) -.021(4) .186(3) 1.0
H(11) -.524(4) .192(3) .395(2) 1.0
H(12) -.421(3) .319(3) .478(2) 1.0
H(13) -.445(3) .155(2) .538(2) 1.0
H(14) -.336(4) .064(3) .459(2) 1.0
H(15) -.115(3) .063(3) .576(2) 1.0
H(16) -.163(4) .071(3) .730(3) 1.0
H(17) -.244(4) .194(4) .735(3) 1.0
H(18) -.340(7) .067(5) .640(4) 1.0
H(19) .081(3) .163(3) .734(2) 1.0
H(20) .032(3) .285(3) .735(2) 1.0
H(21) .164(3) .131(3) .588(2) 1.0
H(22) .417(5) .267(4) .675(3) 1.0
H(23) .345(5) .197(4) .741(3) 1.0
H(24) .327(5) .340(4) .764(3) 1.0
H(25) .251(3) .216(3) .488(2) 1.0
H(26) .348(4) .348(3) .571(2) 1.0
H(27) .257(3) .388(3) .429(2) 1.0
H(28) .162(3) .467(3) .505(2) 1.0
H(29) .882(4) .219(3) -.062(2) 1.0
H(30) .784(4) .104(4) -.057(3) 1.0
H(31) .872(4) .213(3) .046(3) 1.0
H(32) .600(3) .230(2) -.107(2) 1.0
H(33) .554(3) .123(3) -.0029(17) 1.0
H(34) .607(3) .251(2) .087(2) 1.0
H(35) .336(3) .226(2) -.0771(19) 1.0
H(36) .320(4) .198(3) .107(3) 1.0
H(37) .170(5) .183(3) .019(3) 1.0
H(38) .283(4) .076(4) -.004(2) 1.0
H(39) .832(3) .620(2) .052(2) 1.0
H(40) .853(4) .610(3) -.063(2) 1.0
H(41) .870(4) .415(3) -.057(2) 1.0
H(42) .705(4) .401(3) -.128(2) 1.0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(2) N(1) C(14) . . 116.4(2) yes
C(4) N(2) C(6) . . 115.6(3) yes
C(7) N(3) C(8) . . 114.0(2) yes
C(11) N(4) C(13) . . 114.2(2) yes
C(16) N(5) C(21) . . 113.8(2) yes
C(18) N(6) C(20) . 2_665 114.2(2) yes
N(1) C(2) C(1) . . 112.1(3) yes
N(1) C(2) C(3) . . 109.7(2) yes
C(1) C(2) C(3) . . 110.5(3) yes
C(2) C(3) C(4) . . 117.7(2) yes
N(2) C(4) C(3) . . 109.8(2) yes
N(2) C(4) C(5) . . 112.0(3) yes
C(3) C(4) C(5) . . 109.8(3) yes
N(2) C(6) C(7) . . 115.0(3) yes
N(3) C(7) C(6) . . 110.7(3) yes
N(3) C(8) C(9) . . 111.4(3) yes
N(3) C(8) C(10) . . 110.2(2) yes
C(9) C(8) C(10) . . 111.1(3) yes
C(8) C(10) C(11) . . 117.7(3) yes
N(4) C(11) C(10) . . 110.7(2) yes
N(4) C(11) C(12) . . 111.1(3) yes
C(10) C(11) C(12) . . 110.8(3) yes
N(4) C(13) C(14) . . 111.8(3) yes
N(1) C(14) C(13) . . 114.2(3) yes
N(5) C(16) C(15) . . 112.0(2) yes
N(5) C(16) C(17) . . 110.5(2) yes
C(15) C(16) C(17) . . 110.7(2) yes
C(16) C(17) C(18) . . 117.2(2) yes
N(6) C(18) C(17) . . 109.5(2) yes
N(6) C(18) C(19) . . 112.4(3) yes
C(17) C(18) C(19) . . 110.6(2) yes
N(6) C(20) C(21) 2_665 . 111.2(2) yes
N(5) C(21) C(20) . . 112.0(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(2) . 1.465(4) yes
N(1) C(14) . 1.469(4) yes
N(2) C(4) . 1.468(4) yes
N(2) C(6) . 1.460(4) yes
N(3) C(7) . 1.465(4) yes
N(3) C(8) . 1.464(4) yes
N(4) C(11) . 1.463(3) yes
N(4) C(13) . 1.459(4) yes
N(5) C(16) . 1.471(3) yes
N(5) C(21) . 1.461(4) yes
N(6) C(18) . 1.464(3) yes
N(6) C(20) 2_665 1.466(3) yes
C(1) C(2) . 1.519(4) yes
C(2) C(3) . 1.522(4) yes
C(3) C(4) . 1.522(4) yes
C(4) C(5) . 1.525(5) yes
C(6) C(7) . 1.517(5) yes
C(8) C(9) . 1.529(5) yes
C(8) C(10) . 1.511(5) yes
C(10) C(11) . 1.520(5) yes
C(11) C(12) . 1.525(5) yes
C(13) C(14) . 1.516(4) yes
C(15) C(16) . 1.514(4) yes
C(16) C(17) . 1.517(4) yes
C(17) C(18) . 1.527(4) yes
C(18) C(19) . 1.517(4) yes
C(20) N(6) 2_665 1.466(3) yes
C(20) C(21) . 1.503(4) yes
N(1) H(N1) . .94 no
N(1) H(N1') . 1.01 no
N(2) H(N2) . .99 no
N(2) H(N2') . 1.19 no
N(3) H(N3) . 1.03 no
N(3) H(N3') . 1.02 no
N(4) H(N4) . 1.03 no
N(4) H(N4') . .98 no
N(5) H(N5) . 1.02 no
N(5) H(N5') . 1.04 no
N(6) H(N6) . .94 no
N(6) H(N6') . 1.00 no
C(1) H(1) . .94(4) no
C(1) H(2) . 1.09(5) no
C(1) H(3) . 1.01(4) no
C(2) H(4) . 1.01(3) no
C(3) H(5) . 1.03(3) no
C(3) H(6) . 1.00(3) no
C(4) H(7) . 1.03(3) no
C(5) H(8) . 0.97(4) no
C(5) H(9) . 1.07(5) no
C(5) H(10) . 0.98(4) no
C(6) H(11) . 1.03(4) no
C(6) H(12) . 1.00(3) no
C(7) H(13) . 1.06(3) no
C(7) H(14) . 1.10(3) no
C(8) H(15) . .97(3) no
C(9) H(16) . 1.00(4) no
C(9) H(17) . 1.01(4) no
C(9) H(18) . 1.06(6) no
C(10) H(19) . .94(3) no
C(10) H(20) . .97(3) no
C(11) H(21) . 1.00(3) no
C(12) H(22) . 1.09(5) no
C(12) H(23) . .89(5) no
C(12) H(24) . 1.03(5) no
C(13) H(25) . 1.03(3) no
C(13) H(26) . 1.02(3) no
C(14) H(27) . .97(3) no
C(14) H(28) . 1.04(3) no
C(15) H(29) . .95(3) no
C(15) H(30) . .99(4) no
C(15) H(31) . 1.07(4) no
C(16) H(32) . 1.00(3) no
C(17) H(33) . 1.01(3) no
C(17) H(34) . .98(3) no
C(18) H(35) . 1.03(3) no
C(19) H(36) . 1.06(4) no
C(19) H(37) . .96(4) no
C(19) H(38) . 1.01(4) no
C(20) H(39) . 1.05(3) no
C(20) H(40) . 1.10(3) no
C(21) H(41) . .95(3) no
C(21) H(42) . .99(3) no
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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C(14) N(1) C(2) C(3) . . . 174.1(3) yes
C(2) N(1) C(14) C(13) . . . -62.3(2) yes
C(6) N(2) C(4) C(3) . . . -176.5(3) yes
C(4) N(2) C(6) C(7) . . . 60.0(2) yes
C(8) N(3) C(7) C(6) . . . -169.9(3) yes
C(7) N(3) C(8) C(10) . . . 175.0(3) yes
C(13) N(4) C(11) C(10) . . . -173.7(3) yes
C(11) N(4) C(13) C(14) . . . 170.2(3) yes
N(1) C(2) C(3) C(4) . . . -66.7(2) yes
C(2) C(3) C(4) N(2) . . . 68.9(2) yes
N(2) C(6) C(7) N(3) . . . 60.8(2) yes
N(3) C(8) C(10) C(11) . . . -68.1(2) yes
C(8) C(10) C(11) N(4) . . . 68.1(2) yes
N(4) C(13) C(14) N(1) . . . -61.4(2) yes
C(21) N(5) C(16) C(17) . . . -167.5(2) yes
C(16) N(5) C(21) C(20) . . . 172.3(3) yes
C(20) N(6) C(18) C(17) 2_665 . . 174.0(2) yes
C(18) N(6) C(20) C(21) . 2_665 2_665 -167.8(3) yes
N(5) C(16) C(17) C(18) . . . 68.7(2) yes
C(16) C(17) C(18) N(6) . . . -72.3(2) yes
N(6) C(20) C(21) N(5) 2_665 . . -70.8(2) yes