#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/52/2015218.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_2015218
loop_
_publ_author_name
'El Kodadi, Mohamed'
'Ramdani, Abdelkrim'
'Fouad, Malek'
'Eddike, Driss'
'Tillard, Monique'
'Belin, Claude'
_publ_section_title
;
 4-[Bis(1,5-dimethyl-1H-pyrazol-3-ylmethyl)amino]phenol
 monohydrate
;
_journal_coeditor_code           SQ1231
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o735
_journal_page_last               o737
_journal_paper_doi               10.1107/S010827010503461X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H23 N5 O, H2 O'
_chemical_formula_moiety         'C18 H23 N5 O, H2 O'
_chemical_formula_sum            'C18 H25 N5 O2'
_chemical_formula_weight         343.43
_chemical_name_systematic
;
4-[Bis(1,5-dimethyl-1H-pyrazol-3-ylmethyl)amino]phenol monohydrate
;
_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                 126.080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9220(10)
_cell_length_b                   9.4366(6)
_cell_length_c                   16.7990(10)
_cell_measurement_reflns_used    14369
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      3.62
_cell_volume                     1783.7(3)
_computing_cell_refinement       'CrysAlis RED Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14369
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.199
_refine_ls_extinction_coef       0.0072(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.3372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2500
_reflns_number_total             3128
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq1231.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015218
_cod_database_fobs_code          2015218
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_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
_atom_site_type_symbol
O1 1.21937(12) 0.59909(16) 0.44868(11) 0.0363(4) Uani d . 1 . . O
H3O 1.232(3) 0.547(3) 0.503(2) 0.075(9) Uiso d . 1 . . H
N1 0.74396(14) 0.58099(17) 0.11777(11) 0.0271(4) Uani d . 1 . . N
N2 0.59424(14) 0.41870(17) 0.21376(12) 0.0288(4) Uani d . 1 . . N
N3 0.57197(14) 0.27765(18) 0.21324(12) 0.0303(4) Uani d . 1 . . N
N4 0.78734(14) 0.65795(17) -0.07225(11) 0.0283(4) Uani d . 1 . . N
N6 0.83155(14) 0.56142(17) -0.10334(11) 0.0271(4) Uani d . 1 . . N
C1 0.89924(17) 0.5196(2) 0.28913(13) 0.0258(4) Uani d . 1 . . C
H1 0.8433 0.4695 0.2914 0.031 Uiso calc R 1 . . H
C2 1.01619(17) 0.5222(2) 0.37171(14) 0.0276(5) Uani d . 1 . . C
H2 1.0379 0.4741 0.4284 0.033 Uiso calc R 1 . . H
C3 1.10112(17) 0.5963(2) 0.37031(14) 0.0265(5) Uani d . 1 . . C
C4 1.06567(17) 0.6718(2) 0.28687(14) 0.0294(5) Uani d . 1 . . C
H4 1.1211 0.7254 0.2861 0.035 Uiso calc R 1 . . H
C5 0.94874(17) 0.6688(2) 0.20427(14) 0.0279(5) Uani d . 1 . . C
H5 0.9270 0.7204 0.1488 0.033 Uiso calc R 1 . . H
C6 0.86314(16) 0.58998(19) 0.20279(13) 0.0234(4) Uani d . 1 . . C
C7 0.65204(17) 0.5769(2) 0.13425(15) 0.0288(5) Uani d . 1 . . C
H7A 0.5795 0.6167 0.0771 0.035 Uiso calc R 1 . . H
H7B 0.6767 0.6366 0.1903 0.035 Uiso calc R 1 . . H
C8 0.62551(16) 0.4312(2) 0.15281(13) 0.0258(5) Uani d . 1 . . C
C9 0.62393(16) 0.3000(2) 0.11384(14) 0.0301(5) Uani d . 1 . . C
H9 0.6424 0.2815 0.0699 0.036 Uiso calc R 1 . . H
C10 0.58928(16) 0.2036(2) 0.15391(15) 0.0316(5) Uani d . 1 . . C
C11 0.5693(2) 0.0474(2) 0.13903(19) 0.0477(6) Uani d . 1 . . C
H11A 0.4857 0.0280 0.1009 0.072 Uiso calc R 1 . . H
H11B 0.6090 0.0013 0.2019 0.072 Uiso calc R 1 . . H
H11C 0.6004 0.0125 0.1047 0.072 Uiso calc R 1 . . H
C12 0.5350(2) 0.2287(3) 0.27301(16) 0.0415(6) Uani d . 1 . . C
H12A 0.5364 0.1270 0.2748 0.062 Uiso calc R 1 . . H
H12B 0.4559 0.2615 0.2451 0.062 Uiso calc R 1 . . H
H12C 0.5883 0.2650 0.3387 0.062 Uiso calc R 1 . . H
C13 0.71221(18) 0.6542(2) 0.02903(14) 0.0292(5) Uani d . 1 . . C
H13A 0.7393 0.7517 0.0452 0.035 Uiso calc R 1 . . H
H13B 0.6264 0.6553 -0.0184 0.035 Uiso calc R 1 . . H
C14 0.76612(16) 0.5845(2) -0.01640(13) 0.0257(4) Uani d . 1 . . C
C15 0.79692(17) 0.4424(2) -0.01141(14) 0.0288(5) Uani d . 1 . . C
H15 0.7908 0.3703 0.0231 0.035 Uiso calc R 1 . . H
C16 0.83806(17) 0.4308(2) -0.06789(14) 0.0282(5) Uani d . 1 . . C
C17 0.8824(2) 0.3053(2) -0.09077(16) 0.0372(5) Uani d . 1 . . C
H17A 0.9639 0.3202 -0.0656 0.056 Uiso calc R 1 . . H
H17B 0.8354 0.2922 -0.1608 0.056 Uiso calc R 1 . . H
H17C 0.8765 0.2226 -0.0606 0.056 Uiso calc R 1 . . H
C18 0.8688(2) 0.6071(2) -0.16389(16) 0.0367(5) Uani d . 1 . . C
H18A 0.8029 0.6010 -0.2322 0.055 Uiso calc R 1 . . H
H18B 0.9320 0.5472 -0.1515 0.055 Uiso calc R 1 . . H
H18C 0.8963 0.7033 -0.1480 0.055 Uiso calc R 1 . . H
O2 0.26343(17) 0.4500(2) 0.59831(13) 0.0498(5) Uani d . 1 . . O
H1O 0.248(2) 0.358(4) 0.5957(19) 0.063(8) Uiso d . 1 . . H
H2O 0.309(3) 0.478(4) 0.655(3) 0.086(11) Uiso d . 1 . . H
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
_geom_angle_publ_flag
C3 O1 H3O 110.0(17) ?
C6 N1 C13 118.21(15) y
C6 N1 C7 116.55(15) y
C13 N1 C7 115.80(15) y
C8 N2 N3 104.88(16) ?
C10 N3 N2 111.75(17) ?
C10 N3 C12 129.63(19) ?
N2 N3 C12 118.62(18) ?
C14 N4 N6 105.04(15) ?
C16 N6 N4 111.69(15) ?
C16 N6 C18 128.42(17) ?
N4 N6 C18 119.85(16) ?
C2 C1 C6 121.69(18) ?
C2 C1 H1 119.2 ?
C6 C1 H1 119.2 ?
C1 C2 C3 120.27(18) ?
C1 C2 H2 119.9 ?
C3 C2 H2 119.9 ?
O1 C3 C4 118.26(17) ?
O1 C3 C2 123.08(18) ?
C4 C3 C2 118.66(18) ?
C3 C4 C5 120.96(18) ?
C3 C4 H4 119.5 ?
C5 C4 H4 119.5 ?
C4 C5 C6 121.15(18) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C5 C6 C1 117.14(17) ?
C5 C6 N1 122.11(17) y
C1 C6 N1 120.75(17) y
N1 C7 C8 114.43(16) ?
N1 C7 H7A 108.7 ?
C8 C7 H7A 108.7 ?
N1 C7 H7B 108.7 ?
C8 C7 H7B 108.7 ?
H7A C7 H7B 107.6 ?
N2 C8 C9 111.13(17) ?
N2 C8 C7 118.13(17) ?
C9 C8 C7 130.71(18) ?
C10 C9 C8 105.67(18) ?
C10 C9 H9 127.2 ?
C8 C9 H9 127.2 ?
N3 C10 C9 106.57(19) ?
N3 C10 C11 122.5(2) ?
C9 C10 C11 130.9(2) ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N3 C12 H12A 109.5 ?
N3 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
N3 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
N1 C13 C14 111.79(16) ?
N1 C13 H13A 109.3 ?
C14 C13 H13A 109.3 ?
N1 C13 H13B 109.3 ?
C14 C13 H13B 109.3 ?
H13A C13 H13B 107.9 ?
N4 C14 C15 110.77(17) ?
N4 C14 C13 120.97(17) ?
C15 C14 C13 128.22(18) ?
C16 C15 C14 105.90(18) ?
C16 C15 H15 127.1 ?
C14 C15 H15 127.1 ?
N6 C16 C15 106.60(17) ?
N6 C16 C17 122.95(18) ?
C15 C16 C17 130.46(19) ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N6 C18 H18A 109.5 ?
N6 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N6 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 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 C3 . 1.375(2) y
O1 O2 1_655 2.619(2) yes
O1 H3O . 0.96(3) ?
N1 C6 . 1.417(2) y
N1 C13 . 1.456(2) y
N1 C7 . 1.461(2) y
N2 C8 . 1.333(2) y
N2 N3 . 1.366(2) y
N3 C10 . 1.350(3) y
N3 C12 . 1.447(3) y
N4 C14 . 1.332(2) y
N4 N6 . 1.364(2) y
N6 C16 . 1.349(2) y
N6 C18 . 1.453(2) y
C1 C2 . 1.384(3) ?
C1 C6 . 1.392(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.379(3) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.393(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.503(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.394(3) ?
C9 C10 . 1.377(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.494(3) y
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.501(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.396(3) ?
C15 C16 . 1.371(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.486(3) y
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
O2 H1O . 0.89(3) ?
O2 H2O . 0.82(3) ?
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
O2 H1O N4 2_645 0.89(3) 1.93(3) 2.816(2) 172(3)
O2 H2O N2 3_666 0.82(3) 2.03(3) 2.840(2) 169(3)
O1 H3O O2 1_655 0.96(3) 1.66(3) 2.619(2) 174(3)
