#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/13/2221349.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_2221349
loop_
_publ_author_name
'Shi, Ai-E'
'Hou, Yan-Jun'
'Zhang, Yi-Ming'
'Hou, Guang-Feng'
'Gao, Jin-Sheng'
_publ_section_title
;
 1,4-Bis[(1H-pyrazol-1-yl)methyl]benzene dihydrate
;
_journal_coeditor_code           FL2236
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o690
_journal_paper_doi               10.1107/S1600536809007521
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 N4, 2H2 O'
_chemical_formula_moiety         'C14 H14 N4 , 2H2 O'
_chemical_formula_sum            'C14 H18 N4 O2'
_chemical_formula_weight         274.32
_chemical_name_systematic
;
1,4-Bis[(1H-pyrazol-1-yl)methyl]benzene dihydrate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.15(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.680(2)
_cell_length_b                   18.640(8)
_cell_length_c                   16.974(10)
_cell_measurement_reflns_used    8012
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      54.91
_cell_measurement_theta_min      6.49
_cell_volume                     1480.4(13)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14065
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0478
_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)+(0.0547P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                1735
_reflns_number_total             3361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fl2236.cif
_cod_data_source_block           I
_cod_original_cell_volume        1480.6(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221349
_cod_database_fobs_code          2221349
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_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
C C1 0.8625(5) 0.35411(10) 0.69781(13) 0.0727(6) Uani d . 1 . .
H H1 0.7584 0.3209 0.6680 0.087 Uiso calc R 1 . .
C C2 1.0682(5) 0.33893(11) 0.75233(13) 0.0784(6) Uani d . 1 . .
H H2 1.1345 0.2939 0.7677 0.094 Uiso calc R 1 . .
C C3 1.1572(4) 0.40427(12) 0.77993(12) 0.0737(6) Uani d . 1 . .
H H3 1.2983 0.4104 0.8187 0.088 Uiso calc R 1 . .
C C4 0.6675(4) 0.46818(11) 0.63845(12) 0.0709(6) Uani d . 1 . .
H H4 0.6093 0.5124 0.6635 0.085 Uiso calc R 1 . .
H H5 0.4963 0.4419 0.6231 0.085 Uiso calc R 1 . .
C C5 0.8366(3) 0.48549(9) 0.56601(11) 0.0551(4) Uani d . 1 . .
C C6 0.8351(4) 0.43987(10) 0.50232(12) 0.0642(5) Uani d . 1 . .
H H6 0.7232 0.3987 0.5034 0.077 Uiso calc R 1 . .
C C7 1.0049(4) 0.54625(9) 0.56293(11) 0.0622(5) Uani d . 1 . .
H H7 1.0099 0.5779 0.6053 0.075 Uiso calc R 1 . .
C C8 0.5827(4) 0.27680(10) -0.07594(13) 0.0724(6) Uani d . 1 . .
H H8 0.6642 0.2909 -0.1230 0.087 Uiso calc R 1 . .
C C9 0.3835(5) 0.22438(10) -0.06711(15) 0.0776(6) Uani d . 1 . .
H H9 0.3016 0.1955 -0.1061 0.093 Uiso calc R 1 . .
C C10 0.3302(4) 0.22347(9) 0.01191(14) 0.0706(6) Uani d . 1 . .
H H10 0.2015 0.1925 0.0354 0.085 Uiso calc R 1 . .
C C11 0.8187(4) 0.36625(9) 0.01523(13) 0.0663(5) Uani d . 1 . .
H H11 0.9808 0.3674 -0.0195 0.080 Uiso calc R 1 . .
H H12 0.8916 0.3612 0.0688 0.080 Uiso calc R 1 . .
C C12 0.6550(3) 0.43624(8) 0.00771(11) 0.0527(4) Uani d . 1 . .
C C13 0.6725(4) 0.47764(9) -0.05894(11) 0.0616(5) Uani d . 1 . .
H H13 0.7898 0.4630 -0.0995 0.074 Uiso calc R 1 . .
C C14 0.4809(4) 0.45945(9) 0.06678(11) 0.0624(5) Uani d . 1 . .
H H14 0.4663 0.4324 0.1126 0.075 Uiso calc R 1 . .
N N1 0.8358(3) 0.42535(8) 0.69450(8) 0.0559(4) Uani d . 1 . .
N N2 1.0191(3) 0.45779(8) 0.74505(9) 0.0660(4) Uani d . 1 . .
N N3 0.6401(3) 0.30445(7) -0.00459(10) 0.0579(4) Uani d . 1 . .
N N4 0.4843(3) 0.27223(7) 0.05120(10) 0.0638(4) Uani d . 1 . .
O O1 0.4928(3) 0.31462(7) 0.21740(9) 0.0847(4) Uani d . 1 . .
H H15 0.4939 0.3031 0.1690 0.127 Uiso d R 1 . .
H H16 0.3374 0.3373 0.2238 0.127 Uiso d R 1 . .
O O2 0.9966(3) 0.38581(8) 0.24291(10) 0.1062(6) Uani d . 1 . .
H H17 0.9746 0.4311 0.2421 0.159 Uiso d R 1 . .
H H18 0.8329 0.3663 0.2386 0.159 Uiso d 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
N1 C1 C2 . . 107.56(18) ?
N1 C1 H1 . . 126.2 ?
C2 C1 H1 . . 126.2 ?
C1 C2 C3 . . 104.84(18) ?
C1 C2 H2 . . 127.6 ?
C3 C2 H2 . . 127.6 ?
N2 C3 C2 . . 112.08(19) ?
N2 C3 H3 . . 124.0 ?
C2 C3 H3 . . 124.0 ?
N1 C4 C5 . . 111.25(14) ?
N1 C4 H4 . . 109.4 ?
C5 C4 H4 . . 109.4 ?
N1 C4 H5 . . 109.4 ?
C5 C4 H5 . . 109.4 ?
H4 C4 H5 . . 108.0 ?
C6 C5 C7 . . 118.11(16) ?
C6 C5 C4 . . 120.89(17) ?
C7 C5 C4 . . 120.97(18) ?
C7 C6 C5 3_766 . 121.54(17) ?
C7 C6 H6 3_766 . 119.2 ?
C5 C6 H6 . . 119.2 ?
C6 C7 C5 3_766 . 120.36(17) ?
C6 C7 H7 3_766 . 119.8 ?
C5 C7 H7 . . 119.8 ?
N3 C8 C9 . . 107.6(2) ?
N3 C8 H8 . . 126.2 ?
C9 C8 H8 . . 126.2 ?
C8 C9 C10 . . 104.80(19) ?
C8 C9 H9 . . 127.6 ?
C10 C9 H9 . . 127.6 ?
N4 C10 C9 . . 112.01(18) ?
N4 C10 H10 . . 124.0 ?
C9 C10 H10 . . 124.0 ?
N3 C11 C12 . . 111.94(14) ?
N3 C11 H11 . . 109.2 ?
C12 C11 H11 . . 109.2 ?
N3 C11 H12 . . 109.2 ?
C12 C11 H12 . . 109.2 ?
H11 C11 H12 . . 107.9 ?
C13 C12 C14 . . 118.04(16) ?
C13 C12 C11 . . 120.95(17) ?
C14 C12 C11 . . 121.00(16) ?
C12 C13 C14 . 3_665 121.16(16) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 3_665 . 119.4 ?
C12 C14 C13 . 3_665 120.80(16) ?
C12 C14 H14 . . 119.6 ?
C13 C14 H14 3_665 . 119.6 ?
C1 N1 N2 . . 111.26(16) ?
C1 N1 C4 . . 128.31(17) ?
N2 N1 C4 . . 119.92(15) ?
C3 N2 N1 . . 104.26(16) ?
C8 N3 N4 . . 111.25(16) ?
C8 N3 C11 . . 128.06(17) ?
N4 N3 C11 . . 120.37(16) ?
C10 N4 N3 . . 104.34(16) ?
H15 O1 H16 . . 105.7 ?
H17 O2 H18 . . 108.3 ?
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
C1 N1 . 1.335(2) ?
C1 C2 . 1.352(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.367(3) ?
C2 H2 . 0.9300 ?
C3 N2 . 1.322(2) ?
C3 H3 . 0.9300 ?
C4 N1 . 1.460(2) ?
C4 C5 . 1.510(2) ?
C4 H4 . 0.9700 ?
C4 H5 . 0.9700 ?
C5 C6 . 1.375(3) ?
C5 C7 . 1.381(2) ?
C6 C7 3_766 1.374(3) ?
C6 H6 . 0.9300 ?
C7 C6 3_766 1.374(3) ?
C7 H7 . 0.9300 ?
C8 N3 . 1.339(2) ?
C8 C9 . 1.361(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(3) ?
C9 H9 . 0.9300 ?
C10 N4 . 1.331(2) ?
C10 H10 . 0.9300 ?
C11 N3 . 1.459(2) ?
C11 C12 . 1.517(2) ?
C11 H11 . 0.9700 ?
C11 H12 . 0.9700 ?
C12 C13 . 1.373(2) ?
C12 C14 . 1.375(2) ?
C13 C14 3_665 1.380(2) ?
C13 H13 . 0.9300 ?
C14 C13 3_665 1.380(2) ?
C14 H14 . 0.9300 ?
N1 N2 . 1.345(2) ?
N3 N4 . 1.348(2) ?
O1 H15 . 0.8500 ?
O1 H16 . 0.8500 ?
O2 H17 . 0.8500 ?
O2 H18 . 0.8500 ?
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 H15 N4 . 0.85 2.08 2.929(3) 177.9
O1 H16 O2 1_455 0.85 1.87 2.717(2) 177.3
O2 H17 N2 3_766 0.85 2.08 2.923(2) 169.7
O2 H18 O1 . 0.85 1.89 2.733(2) 171.6
