#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221250.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_2221250
loop_
_publ_author_name
'Ma, Yanni'
'Zhou, Le'
'Deng, Dongsheng'
'Ji, Baoming'
_publ_section_title
;
 4,4',6,6'-Tetramethyl-2,2'-bipyrimidine hexahydrate
;
_journal_coeditor_code           AT2743
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o848
_journal_page_last               o849
_journal_paper_doi               10.1107/S1600536809010095
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H14 N4, 6H2 O'
_chemical_formula_moiety         'C12 H14 N4, 6(H2 O)'
_chemical_formula_sum            'C12 H26 N4 O6'
_chemical_formula_weight         322.37
_chemical_name_systematic
;
4,4',6,6'-Tetramethyl-2,2'-bipyrimidine hexahydrate
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.233(3)
_cell_angle_beta                 91.774(4)
_cell_angle_gamma                102.599(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8622(19)
_cell_length_b                   11.098(3)
_cell_length_c                   11.750(3)
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0.979
_cell_measurement_theta_min      0.961
_cell_volume                     862.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6492
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.154
_refine_ls_extinction_coef       0.045(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXS97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0473
_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)+(0.074P)²+0.0388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1481
_reflns_number_gt                2026
_reflns_number_total             3196
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2743.cif
_cod_data_source_block           I
_cod_original_cell_volume        862.4(4)
_cod_database_code               2221250
_cod_database_fobs_code          2221250
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.0078(2) 0.66049(15) 0.38126(13) 0.0642(5) Uani d . 1 . .
H H1W 0.9576 0.6341 0.3142 0.096 Uiso d R 1 . .
H H2W 0.9194 0.6501 0.4285 0.096 Uiso d R 1 . .
O O2 0.4638(2) 0.32153(14) 0.82784(13) 0.0576(5) Uani d . 1 . .
H H3W 0.3978 0.2491 0.8284 0.086 Uiso d R 1 . .
H H4W 0.5591 0.3379 0.8787 0.086 Uiso d R 1 . .
O O3 0.1279(3) 0.42962(14) 0.85957(13) 0.0620(5) Uani d . 1 . .
H H5W 0.0432 0.3909 0.8985 0.093 Uiso d R 1 . .
H H6W 0.2226 0.3952 0.8493 0.093 Uiso d R 1 . .
O O4 0.6255(3) 0.40256(16) 0.62491(14) 0.0672(5) Uani d . 1 . .
H H7W 0.5777 0.3790 0.6846 0.101 Uiso d R 1 . .
H H8W 0.7336 0.3788 0.6155 0.101 Uiso d R 1 . .
O O5 0.2031(2) 0.66114(14) 1.01180(14) 0.0624(5) Uani d . 1 . .
H H9W 0.2119 0.7281 0.9869 0.094 Uiso d R 1 . .
H H10W 0.1897 0.6013 0.9586 0.094 Uiso d R 1 . .
O O6 0.7043(3) 0.63916(16) 0.54052(14) 0.0705(5) Uani d . 1 . .
H H11W 0.6024 0.6411 0.5015 0.106 Uiso d R 1 . .
H H12W 0.6844 0.5744 0.5710 0.106 Uiso d R 1 . .
N N1 0.2840(3) 0.14305(16) 0.99505(14) 0.0417(4) Uani d . 1 . .
N N2 0.2855(3) 0.04691(15) 0.77127(13) 0.0417(4) Uani d . 1 . .
N N3 0.2336(2) -0.15832(15) 0.82104(14) 0.0403(4) Uani d . 1 . .
N N4 0.2327(2) -0.06158(15) 1.04606(14) 0.0407(4) Uani d . 1 . .
C C1 0.1870(4) -0.1038(2) 1.24073(18) 0.0559(6) Uani d . 1 . .
H H1A 0.0530 -0.1535 1.2264 0.084 Uiso calc R 1 . .
H H1B 0.2033 -0.0587 1.3178 0.084 Uiso calc R 1 . .
H H1C 0.2801 -0.1572 1.2319 0.084 Uiso calc R 1 . .
C C2 0.2256(3) -0.0134(2) 1.15686(17) 0.0414(5) Uani d . 1 . .
C C3 0.2480(3) 0.1139(2) 1.18979(17) 0.0452(5) Uani d . 1 . .
H H3 0.2434 0.1471 1.2667 0.054 Uiso calc R 1 . .
C C4 0.2775(3) 0.19090(19) 1.10592(17) 0.0432(5) Uani d . 1 . .
C C5 0.3011(4) 0.3293(2) 1.1331(2) 0.0632(7) Uani d . 1 . .
H H5A 0.4190 0.3704 1.1002 0.095 Uiso calc R 1 . .
H H5B 0.3133 0.3543 1.2152 0.095 Uiso calc R 1 . .
H H5C 0.1861 0.3522 1.1015 0.095 Uiso calc R 1 . .
C C6 0.2612(3) 0.01975(18) 0.97125(16) 0.0365(5) Uani d . 1 . .
C C7 0.2621(3) -0.03399(18) 0.84670(16) 0.0363(5) Uani d . 1 . .
C C8 0.1946(4) -0.3443(2) 0.6791(2) 0.0617(7) Uani d . 1 . .
H H8A 0.3139 -0.3691 0.7017 0.093 Uiso calc R 1 . .
H H8B 0.1661 -0.3685 0.5975 0.093 Uiso calc R 1 . .
H H8C 0.0846 -0.3845 0.7189 0.093 Uiso calc R 1 . .
C C9 0.2245(3) -0.20604(19) 0.70895(17) 0.0432(5) Uani d . 1 . .
C C10 0.2398(3) -0.1290(2) 0.62551(18) 0.0496(6) Uani d . 1 . .
H H10 0.2286 -0.1625 0.5477 0.060 Uiso calc R 1 . .
C C11 0.2719(3) -0.00161(19) 0.65939(17) 0.0449(5) Uani d . 1 . .
C C12 0.2935(4) 0.0891(2) 0.57525(19) 0.0644(7) Uani d . 1 . .
H H12A 0.1977 0.1402 0.5887 0.097 Uiso calc R 1 . .
H H12B 0.2705 0.0442 0.4982 0.097 Uiso calc R 1 . .
H H12C 0.4262 0.1413 0.5849 0.097 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1W O1 H2W . . 110.2 ?
H3W O2 H4W . . 109.0 ?
H5W O3 H6W . . 111.2 ?
H7W O4 H8W . . 108.4 ?
H9W O5 H10W . . 111.6 ?
H11W O6 H12W . . 109.9 ?
C6 N1 C4 . . 116.54(17) ?
C7 N2 C11 . . 116.80(17) ?
C7 N3 C9 . . 116.70(17) ?
C6 N4 C2 . . 116.31(18) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N4 C2 C3 . . 120.80(18) ?
N4 C2 C1 . . 116.81(19) ?
C3 C2 C1 . . 122.37(19) ?
C2 C3 C4 . . 118.69(19) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
N1 C4 C3 . . 120.68(19) ?
N1 C4 C5 . . 116.81(19) ?
C3 C4 C5 . . 122.50(19) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N1 C6 N4 . . 126.97(18) ?
N1 C6 C7 . . 116.44(17) ?
N4 C6 C7 . . 116.57(18) ?
N3 C7 N2 . . 126.13(18) ?
N3 C7 C6 . . 117.13(17) ?
N2 C7 C6 . . 116.70(17) ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N3 C9 C10 . . 120.62(19) ?
N3 C9 C8 . . 117.30(18) ?
C10 C9 C8 . . 122.07(19) ?
C11 C10 C9 . . 118.96(19) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
N2 C11 C10 . . 120.71(18) ?
N2 C11 C12 . . 116.59(19) ?
C10 C11 C12 . . 122.71(19) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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
O1 H1W . 0.8358 ?
O1 H2W . 0.8355 ?
O2 H3W . 0.8334 ?
O2 H4W . 0.8431 ?
O3 H5W . 0.8342 ?
O3 H6W . 0.8269 ?
O4 H7W . 0.8351 ?
O4 H8W . 0.8443 ?
O5 H9W . 0.8278 ?
O5 H10W . 0.8314 ?
O6 H11W . 0.8302 ?
O6 H12W . 0.8353 ?
N1 C6 . 1.330(2) ?
N1 C4 . 1.340(3) ?
N2 C7 . 1.338(2) ?
N2 C11 . 1.340(3) ?
N3 C7 . 1.339(2) ?
N3 C9 . 1.341(3) ?
N4 C6 . 1.337(2) ?
N4 C2 . 1.341(3) ?
C1 C2 . 1.493(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.383(3) ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.496(3) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.500(3) ?
C8 C9 . 1.492(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.383(3) ?
C10 C11 . 1.379(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.498(3) ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1W O3 2_666 0.84 2.08 2.914(2) 172.2
O1 H2W O6 . 0.84 2.00 2.837(2) 175.3
O2 H3W N2 . 0.83 2.20 2.995(2) 158.3
O2 H3W N1 . 0.83 2.49 3.083(2) 129.4
O2 H4W O5 2_667 0.84 2.04 2.872(2) 167.4
O3 H5W O5 2_567 0.83 2.04 2.847(2) 163.0
O3 H6W O2 . 0.83 2.01 2.832(2) 176.6
O4 H7W O2 . 0.84 2.01 2.841(2) 179.7
O4 H8W O1 2_766 0.84 1.92 2.755(2) 170.7
O5 H9W N4 1_565 0.83 2.31 3.007(2) 142.2
O5 H9W N3 1_565 0.83 2.46 3.196(2) 148.7
O5 H10W O3 . 0.83 2.04 2.849(2) 165.5
O6 H11W O4 2_666 0.83 2.05 2.851(2) 161.7
O6 H12W O4 . 0.84 2.06 2.886(2) 172.7
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N4 C2 C3 . . . . -0.3(3) ?
C6 N4 C2 C1 . . . . 178.04(18) ?
N4 C2 C3 C4 . . . . 0.2(3) ?
C1 C2 C3 C4 . . . . -178.1(2) ?
C6 N1 C4 C3 . . . . -0.1(3) ?
C6 N1 C4 C5 . . . . -179.45(19) ?
C2 C3 C4 N1 . . . . 0.1(3) ?
C2 C3 C4 C5 . . . . 179.3(2) ?
C4 N1 C6 N4 . . . . 0.0(3) ?
C4 N1 C6 C7 . . . . 178.16(17) ?
C2 N4 C6 N1 . . . . 0.3(3) ?
C2 N4 C6 C7 . . . . -177.94(17) ?
C9 N3 C7 N2 . . . . -1.1(3) ?
C9 N3 C7 C6 . . . . 176.71(17) ?
C11 N2 C7 N3 . . . . 2.5(3) ?
C11 N2 C7 C6 . . . . -175.32(18) ?
N1 C6 C7 N3 . . . . -178.13(16) ?
N4 C6 C7 N3 . . . . 0.3(3) ?
N1 C6 C7 N2 . . . . -0.1(3) ?
N4 C6 C7 N2 . . . . 178.33(16) ?
C7 N3 C9 C10 . . . . -1.4(3) ?
C7 N3 C9 C8 . . . . 179.46(19) ?
N3 C9 C10 C11 . . . . 2.3(3) ?
C8 C9 C10 C11 . . . . -178.5(2) ?
C7 N2 C11 C10 . . . . -1.4(3) ?
C7 N2 C11 C12 . . . . 178.63(19) ?
C9 C10 C11 N2 . . . . -0.9(3) ?
C9 C10 C11 C12 . . . . 179.1(2) ?
