#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151957
loop_
_publ_author_name
'Trávníček, Zdeněk'
'Novotná, Radka'
'Marek, Jaromír'
'Popa, Igor'
'Sipl, Michal'
_publ_section_title
;
 Transformations of the natural cytokinin N6-isopentenyladenine in
 aqueous acidic media: structural aspects.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5703
_journal_page_last               5713
_journal_paper_doi               10.1039/c1ob05649b
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C9 H17 N5, 2(H2 O), 2(Cl) '
_chemical_formula_sum            'C9 H21 Cl2 N5 O2'
_chemical_formula_weight         302.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.240(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0591(4)
_cell_length_b                   15.6552(7)
_cell_length_c                   13.2731(6)
_cell_measurement_reflns_used    5643
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.683
_cell_measurement_theta_min      2.7055
_cell_volume                     1451.69(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.3611
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM4 + CCD'
_diffrn_measurement_method       'rotation method, ω--scan'
_diffrn_radiation_monochromator  'Enhance (Oxford Diffraction)'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7984
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2562
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0300P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                2434
_reflns_number_total             2562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05649b.txt
_cod_data_source_block           Travnicek3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7151957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.15064(5) 0.63882(2) 0.13284(2) 0.01550(11) Uani 1 1 d . . .
N1 N 0.60433(17) 0.65272(8) 0.04975(9) 0.0135(3) Uani 1 1 d . . .
H1 H 0.5537 0.7007 0.0679 0.016 Uiso 1 1 calc R . .
C2 C 0.6166(2) 0.62948(10) -0.04408(11) 0.0156(3) Uani 1 1 d . . .
H2 H 0.5735 0.6619 -0.1035 0.019 Uiso 1 1 calc R . .
N3 N 0.70034(17) 0.55233(8) -0.04230(9) 0.0143(3) Uani 1 1 d . . .
H3 H 0.7222 0.5234 -0.0963 0.017 Uiso 1 1 calc R . .
C4 C 0.74694(19) 0.52530(9) 0.05716(10) 0.0128(3) Uani 1 1 d . . .
C5 C 0.68433(19) 0.58924(9) 0.11607(10) 0.0121(3) Uani 1 1 d . . .
N6 N 0.8271(2) 0.44848(9) 0.08116(11) 0.0188(3) Uani 1 1 d . . .
H6A H 0.851(3) 0.4185(12) 0.0307(15) 0.023 Uiso 1 1 d . . .
H6B H 0.900(3) 0.4427(12) 0.1379(15) 0.023 Uiso 1 1 d . . .
C7 C 0.6959(2) 0.59492(9) 0.22605(10) 0.0115(3) Uani 1 1 d . . .
N8 N 0.55344(17) 0.62811(8) 0.26681(9) 0.0129(3) Uani 1 1 d . . .
H8 H 0.4482 0.6432 0.2270 0.016 Uiso 1 1 calc R . .
C9 C 0.5660(2) 0.64068(9) 0.37844(10) 0.0152(3) Uani 1 1 d . . .
C10 C 0.6755(2) 0.56371(10) 0.42836(11) 0.0175(3) Uani 1 1 d . . .
H10A H 0.6923 0.5704 0.5033 0.021 Uiso 1 1 calc R . .
H10B H 0.6002 0.5111 0.4107 0.021 Uiso 1 1 calc R . .
C11 C 0.8704(2) 0.55498(11) 0.39353(11) 0.0208(3) Uani 1 1 d . . .
H11A H 0.9580 0.5993 0.4267 0.025 Uiso 1 1 calc R . .
H11B H 0.9255 0.4983 0.4136 0.025 Uiso 1 1 calc R . .
N12 N 0.85147(17) 0.56451(8) 0.28234(9) 0.0164(3) Uani 1 1 d . . .
H12 H 0.9486 0.5492 0.2516 0.020 Uiso 1 1 calc R . .
C13 C 0.3618(2) 0.64210(12) 0.40431(12) 0.0252(4) Uani 1 1 d . . .
H13A H 0.2900 0.6886 0.3671 0.038 Uiso 1 1 calc R . .
H13B H 0.3655 0.6510 0.4776 0.038 Uiso 1 1 calc R . .
H13C H 0.2990 0.5875 0.3848 0.038 Uiso 1 1 calc R . .
C14 C 0.6683(3) 0.72480(11) 0.40630(12) 0.0269(4) Uani 1 1 d . . .
H14A H 0.7943 0.7239 0.3835 0.040 Uiso 1 1 calc R . .
H14B H 0.6841 0.7326 0.4803 0.040 Uiso 1 1 calc R . .
H14C H 0.5924 0.7720 0.3731 0.040 Uiso 1 1 calc R . .
O1 O 0.57695(17) 0.81401(7) 0.11232(9) 0.0222(2) Uani 1 1 d D . .
H1V H 0.498(3) 0.8367(12) 0.1506(13) 0.027 Uiso 1 1 d D . .
H1W H 0.689(2) 0.8196(12) 0.1484(13) 0.027 Uiso 1 1 d D . .
Cl1 Cl 0.30313(5) 0.92445(2) 0.23072(3) 0.01835(11) Uani 1 1 d . . .
O2 O 0.94892(17) 0.80141(8) 0.21352(10) 0.0276(3) Uani 1 1 d D . .
H2V H 1.039(3) 0.8396(12) 0.2121(15) 0.033 Uiso 1 1 d D . .
H2W H 1.000(3) 0.7541(11) 0.1912(15) 0.033 Uiso 1 1 d D . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.03(12) . . ?
C2 N1 H1 125.5 . . ?
C5 N1 H1 125.5 . . ?
N1 C2 N3 108.74(12) . . ?
N1 C2 H2 125.6 . . ?
N3 C2 H2 125.6 . . ?
C2 N3 C4 109.66(12) . . ?
C2 N3 H3 125.2 . . ?
C4 N3 H3 125.2 . . ?
N6 C4 N3 122.28(13) . . ?
N6 C4 C5 132.10(13) . . ?
N3 C4 C5 105.52(12) . . ?
C4 C5 N1 107.04(12) . . ?
C4 C5 C7 129.55(13) . . ?
N1 C5 C7 123.41(12) . . ?
C4 N6 H6A 115.3(12) . . ?
C4 N6 H6B 118.9(12) . . ?
H6A N6 H6B 118.2(17) . . ?
N8 C7 N12 122.06(12) . . ?
N8 C7 C5 120.09(12) . . ?
N12 C7 C5 117.84(12) . . ?
C7 N8 C9 121.54(12) . . ?
C7 N8 H8 119.2 . . ?
C9 N8 H8 119.2 . . ?
N8 C9 C14 108.40(12) . . ?
N8 C9 C13 107.62(12) . . ?
C14 C9 C13 111.26(13) . . ?
N8 C9 C10 106.38(11) . . ?
C14 C9 C10 112.55(13) . . ?
C13 C9 C10 110.36(13) . . ?
C11 C10 C9 111.23(12) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N12 C11 C10 109.91(12) . . ?
N12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C7 N12 C11 123.43(12) . . ?
C7 N12 H12 118.3 . . ?
C11 N12 H12 118.3 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H1V O1 H1W 103.9(17) . . ?
H2V O2 H2W 103.3(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3123(19) . ?
N1 C5 1.3925(18) . ?
N1 H1 0.8800 . ?
C2 N3 1.343(2) . ?
C2 H2 0.9500 . ?
N3 C4 1.3804(18) . ?
N3 H3 0.8800 . ?
C4 N6 1.348(2) . ?
C4 C5 1.381(2) . ?
C5 C7 1.4531(19) . ?
N6 H6A 0.85(2) . ?
N6 H6B 0.85(2) . ?
C7 N8 1.3151(19) . ?
C7 N12 1.3251(19) . ?
N8 C9 1.4846(18) . ?
N8 H8 0.8800 . ?
C9 C14 1.522(2) . ?
C9 C13 1.529(2) . ?
C9 C10 1.530(2) . ?
C10 C11 1.519(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.4704(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 H12 0.8800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1 H1V 0.879(15) . ?
O1 H1W 0.868(15) . ?
O2 H2V 0.878(15) . ?
O2 H2W 0.892(15) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653517
