#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/06/2000643.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_2000643
loop_
_publ_author_name
'Reibenspies, J. H.'
_publ_contact_author
;
       Dr. Joseph H. Reibenspies
       Department of Chemistry
       Texas A & M University
       College Station, Texas 77845
       U.S.A.
;
_publ_section_title
;
 Structure of 1,4,7,10-tetraazacyclododecane trihydrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1717
_journal_page_last               1718
_journal_paper_doi               10.1107/S0108270192006723
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C8 H20 N4, 3(H2 O)'
_chemical_formula_sum            'C8 H26 N4 O3'
_chemical_formula_weight         226.3
_chemical_name_common            cyclen
_chemical_name_systematic
;
1,4,7,10-tetrazacyclododecane
;
_space_group_IT_number           68
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2a 2ac'
_symmetry_space_group_name_H-M   'C c c a :2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.636(4)
_cell_length_b                   16.873(3)
_cell_length_c                   8.881(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      9.19
_cell_volume                     2492.9(9)
_computing_data_collection       'Siemens P3VAX version 3.4'
_computing_data_reduction        'REFRED (Reibenspies, 1992)'
_computing_publication_material  'SHELXTL-PLUS '
_computing_structure_refinement  SHELXTL-PLUS
_computing_structure_solution    'SHELXTL-PLUS (Sheldrick, 1990)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Siemens R3m/V diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_sigmaI/netI    0.04
_diffrn_reflns_number            1273
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.27
_refine_ls_extinction_coef       0.0004(2)
_refine_ls_extinction_method     'Larsen (1967)'
_refine_ls_goodness_of_fit_all   1.302
_refine_ls_goodness_of_fit_obs   1.452
_refine_ls_matrix_type           full
_refine_ls_number_constraints    6
_refine_ls_number_parameters     71
_refine_ls_number_reflns         814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_obs          0.0520
_refine_ls_shift/esd_max         0.0021
_refine_ls_shift/esd_mean        0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F)+0.0005F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0622
_refine_ls_wR_factor_obs         0.0586
_reflns_number_observed          814
_reflns_number_total             1270
_reflns_observed_criterion       refln_observed_if_F_>_2.5_\s(F)
_cod_data_source_file            st1013.cif
_cod_data_source_block           cyclen
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(F)+0.0005F^2^]' 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^(F)+0.0005F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2492.9(8)
_cod_original_sg_symbol_Hall     '-C 2b 2ac'
_cod_original_sg_symbol_H-M      'C c c a'
_cod_database_code               2000643
loop_
_symmetry_equiv_pos_as_xyz
'    +x,     +y,     +z'
' 1/2+x,  1/2+y,     +z'
'    -x,     -y,     -z'
' 1/2-x,  1/2-y,     -z'
' 1/2-x,     -y,     +z'
'   1-x,  1/2-y,     +z'
'-1/2+x,     +y,     -z'
'    +x,  1/2+y,     -z'
'    -x,     +y,  1/2-z'
' 1/2-x,  1/2+y,  1/2-z'
'    +x,     -y, -1/2+z'
' 1/2+x,  1/2-y, -1/2+z'
' 1/2+x,     -y,  1/2-z'
'   1+x,  1/2-y,  1/2-z'
'-1/2-x,     +y, -1/2+z'
'    -x,  1/2+y, -1/2+z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O(1) .045(2) .061(2) .043(2) 0 .004(2) 0
O(2) .067(2) .048(2) .060(2) -.016(2) 0 0
O(3) .0350(10) .0410(10) .046(2) 0 0 -.0040(10)
N(1) .0390(10) .0360(10) .0320(10) -.0040(10) -.0020(10) -.0010(10)
N(2) .0350(10) .0350(10) .0310(10) .0000(10) -.0020(10) -.0010(10)
C(1) .0370(10) .0370(10) .0340(10) .0040(10) .0020(10) .0000(10)
C(2) .0340(10) .039(2) .044(2) .0010(10) .0040(10) .0010(10)
C(3) .037(2) .039(2) .037(2) .0030(10) -.0010(10) .0060(10)
C(4) .040(2) .0340(10) .041(2) .0020(10) -.0030(10) .0010(10)
loop_
_atom_site_label
_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_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
O(1) .5000 .2500 -.0269(3) .0490(10) Uani ? ? S
O(2) .5000 .1484(2) .2500 .0580(10) Uani ? ? S
O(3) .12680(10) .2500 .2500 .0410(10) Uani ? ? S
N(1) .37020(10) .02300(10) .1368(2) .0360(10) Uani ? ? .
N(2) .22200(10) .12400(10) .1367(2) .0340(10) Uani ? ? .
C(1) .3335(2) -.1024(2) .0152(3) .0360(10) Uani ? ? .
C(2) .4010(2) -.0513(2) .0753(3) .0390(10) Uani ? ? .
C(3) .3534(2) .0826(2) .0211(3) .0380(10) Uani ? ? .
C(4) .3014(2) .1491(2) .0840(3) .0380(10) Uani ? ? .
H(1O1) .5423 .2474 -.0874 .080 Uiso d ? RT
H(1O2) .4848 .1902 .1728 .080 Uiso d ? RT
H(1O3) .1640 .2039 .2259 .080 Uiso d ? RT
H(1) .4026 .0499 .1996 .080 Uiso d ? RT
H(2) .2279 .0799 .1927 .080 Uiso d ? RT
H(1A) .3546 -.1500 -.0293 .080 Uiso calc C(1) RT
H(1B) .3051 -.0733 -.0613 .080 Uiso calc C(1) RT
H(2A) .4277 -.0802 .1540 .080 Uiso calc C(2) RT
H(2B) .4396 -.0415 -.0032 .080 Uiso calc C(2) RT
H(3A) .3226 .0573 -.0569 .080 Uiso calc C(3) RT
H(3B) .4021 .1025 -.0234 .080 Uiso calc C(3) RT
H(4A) .3291 .1716 .1688 .080 Uiso calc C(4) RT
H(4B) .2950 .1896 .0088 .080 Uiso calc C(4) RT
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.2B
H 0 0 International_Tables_Vol_IV_Table_2.2B
N 0.029 0.018 International_Tables_Vol_IV_Table_2.2B
O 0.047 0.032 International_Tables_Vol_IV_Table_2.2B
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 0
-2 -4 0
-1 -1 -2
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H(1O1) O(1) H(1O1) . . 6_555 105.0(10) ?
H(1O2) O(2) H(1O2) . . 9_655 92.0(10) ?
H(1O3) O(3) H(1O3) . . 14_455 105.0(10) ?
H(1) N(1) C(2) . . . 117.0(10) ?
H(1) N(1) C(3) . . . 101.0(10) ?
C(2) N(1) C(3) . . . 113.2(2) yes
H(2) N(2) C(4) . . . 108.0(10) ?
H(2) N(2) C(1) . . 5_555 106.0(10) ?
C(4) N(2) C(1) . . 5_555 113.9(2) yes
H(1A) C(1) H(1B) . . . 108.0(10) ?
H(1A) C(1) C(2) . . . 110.0(10) ?
H(1B) C(1) C(2) . . . 109.0(10) ?
H(1A) C(1) N(2) . . 5_555 109.0(10) ?
H(1B) C(1) N(2) . . 5_555 109.0(10) ?
C(2) C(1) N(2) . . 5_555 110.5(2) yes
N(1) C(2) C(1) . . . 111.1(2) yes
N(1) C(2) H(2A) . . . 109.0(10) ?
C(1) C(2) H(2A) . . . 108.0(10) ?
N(1) C(2) H(2B) . . . 111.0(10) ?
C(1) C(2) H(2B) . . . 109.0(10) ?
H(2A) C(2) H(2B) . . . 108.0(10) ?
N(1) C(3) H(3A) . . . 108.0(10) ?
N(1) C(3) H(3B) . . . 112.0(10) ?
H(3A) C(3) H(3B) . . . 108.0(10) ?
N(1) C(3) C(4) . . . 110.9(2) yes
H(3A) C(3) C(4) . . . 107.0(10) ?
H(3B) C(3) C(4) . . . 112.0(10) ?
N(2) C(4) C(3) . . . 114.7(2) yes
N(2) C(4) H(4A) . . . 107.0(10) ?
C(3) C(4) H(4A) . . . 109.0(10) ?
N(2) C(4) H(4B) . . . 109.0(10) ?
C(3) C(4) H(4B) . . . 109.0(10) ?
H(4A) C(4) H(4B) . . . 108.0(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) H(1O1) . . 0.886 ?
O(1) H(1O1) . 6_555 0.886 ?
O(2) H(1O2) . . 1.016 ?
O(2) H(1O2) . 9_655 1.016 ?
O(3) H(1O3) . . 1.017 ?
O(3) H(1O3) . 14_455 1.017 ?
N(1) H(1) . . 0.900 ?
N(1) C(2) . . 1.460(3) yes
N(1) C(3) . . 1.465(3) yes
N(2) H(2) . . 0.900 ?
N(2) C(4) . . 1.464(3) yes
N(2) C(1) . 5_555 1.466(3) yes
C(1) H(1A) . . 0.961 ?
C(1) H(1B) . . 0.961 ?
C(1) C(2) . . 1.513(4) yes
C(3) C(4) . . 1.523(4) yes
C(1) N(2) . 5_555 1.466(3) yes
C(2) H(2A) . . 0.961 ?
C(2) H(2B) . . 0.962 ?
C(3) H(3A) . . 0.962 ?
C(3) H(3B) . . 0.962 ?
C(4) H(4A) . . 0.961 ?
C(4) H(4B) . . 0.961 ?
