##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
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##############################################################################
data_I
_audit_creation_method SHELXL-97
_database_code_depnum_ccdc_archive 'CCDC 988870'
_chemical_name_systematic
;\
2-(3-{(3R,4R)-4-Methyl-3-[methyl(7H-\
pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}oxetan-\
3-yl)acetonitrile monohydrate
;
_chemical_name_common ?
_chemical_formula_moiety 'C18 H24 N6 O, H2 O'
_chemical_formula_sum 'C18 H26 N6 O2'
_chemical_formula_iupac 'C18 H24 N6 O, H2 O'
_chemical_formula_weight 358.45
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 6.6088(6)
_cell_length_b 10.1483(8)
_cell_length_c 26.813(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1798.3(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 6886
_cell_measurement_theta_min 2.5
_cell_measurement_theta_max 27.8
_cell_measurement_temperature 193(2)
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.27
_exptl_crystal_size_min 0.06
_exptl_crystal_density_diffrn 1.324
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 768
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type none
_exptl_special_details ?
_diffrn_ambient_temperature 193(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Stoe IPDS 2T'
_diffrn_measurement_device '2-circle goniometer'
_diffrn_measurement_method 'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number 6672
_diffrn_reflns_av_R_equivalents 0.0789
_diffrn_reflns_av_sigmaI/netI 0.1509
_diffrn_reflns_theta_min 3.17
_diffrn_reflns_theta_max 28.00
_diffrn_reflns_theta_full 28.00
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -29
_diffrn_reflns_limit_l_max 35
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 4184
_reflns_number_gt 1716
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.1784
_refine_ls_R_factor_gt 0.0623
_refine_ls_wR_factor_ref 0.1504
_refine_ls_wR_factor_obs 0.1132
_refine_ls_goodness_of_fit_ref 0.904
_refine_ls_restrained_S_all 0.904
_refine_ls_number_reflns 4184
_refine_ls_number_parameters 246
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.192
_refine_diff_density_min -0.219
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'X-AREA (Stoe & Cie, 2010)'
_computing_cell_refinement 'X-AREA (Stoe & Cie, 2010)'
_computing_data_reduction 'X-RED (Stoe & Cie, 2010)'
_computing_structure_solution 'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'PLATON (Spek, 2009)'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.1280(5) 0.1062(4) 0.42472(12) 0.0485(10) Uani d . 1 1 . .
H H1 0.1160 0.1276 0.4564 0.058 Uiso calc R 1 1 . .
C C2 0.2919(7) 0.0433(4) 0.40332(16) 0.0485(12) Uani d . 1 1 . .
H H2 0.4106 0.0163 0.4205 0.058 Uiso calc R 1 1 . .
C C3 0.2563(7) 0.0264(4) 0.35393(15) 0.0439(11) Uani d . 1 1 . .
H H3 0.3446 -0.0139 0.3305 0.053 Uiso calc R 1 1 . .
C C4 0.0579(7) 0.0814(4) 0.34361(15) 0.0423(11) Uani d . 1 1 . .
C C5 -0.0680(7) 0.1060(4) 0.30217(14) 0.0391(10) Uani d . 1 1 . .
N N6 -0.2486(6) 0.1667(4) 0.30983(12) 0.0449(9) Uani d . 1 1 . .
C C7 -0.2941(7) 0.2044(4) 0.35573(15) 0.0476(11) Uani d . 1 1 . .
H H7 -0.4211 0.2473 0.3591 0.057 Uiso calc R 1 1 . .
N N8 -0.1909(6) 0.1916(4) 0.39726(12) 0.0470(9) Uani d . 1 1 . .
C C9 -0.0105(7) 0.1291(4) 0.38869(14) 0.0413(10) Uani d . 1 1 . .
N N10 -0.0216(5) 0.0778(3) 0.25423(11) 0.0396(8) Uani d . 1 1 . .
C C11 0.1748(6) 0.0150(4) 0.24320(14) 0.0451(11) Uani d . 1 1 . .
H H11A 0.1885 0.0029 0.2071 0.068 Uiso calc R 1 1 . .
H H11B 0.1815 -0.0709 0.2598 0.068 Uiso calc R 1 1 . .
H H11C 0.2847 0.0712 0.2554 0.068 Uiso calc R 1 1 . .
C C12 -0.1610(7) 0.1075(4) 0.21317(14) 0.0415(10) Uani d . 1 1 . .
H H12 -0.2699 0.1634 0.2281 0.050 Uiso calc R 1 1 . .
C C13 -0.0683(7) 0.1906(4) 0.17183(13) 0.0419(11) Uani d . 1 1 . .
H H13A -0.1782 0.2339 0.1528 0.050 Uiso calc R 1 1 . .
H H13B 0.0160 0.2606 0.1870 0.050 Uiso calc R 1 1 . .
N N14 0.0562(5) 0.1135(3) 0.13743(11) 0.0401(9) Uani d . 1 1 . .
C C15 -0.0684(7) 0.0153(4) 0.11233(14) 0.0437(11) Uani d . 1 1 . .
H H15A 0.0130 -0.0318 0.0870 0.052 Uiso calc R 1 1 . .
H H15B -0.1832 0.0588 0.0953 0.052 Uiso calc R 1 1 . .
C C16 -0.1472(7) -0.0818(4) 0.15091(15) 0.0474(11) Uani d . 1 1 . .
H H16A -0.0314 -0.1284 0.1663 0.057 Uiso calc R 1 1 . .
H H16B -0.2331 -0.1483 0.1341 0.057 Uiso calc R 1 1 . .
C C17 -0.2698(7) -0.0137(4) 0.19154(14) 0.0424(11) Uani d . 1 1 . .
H H17 -0.3970 0.0189 0.1755 0.051 Uiso calc R 1 1 . .
C C18 -0.3324(7) -0.1107(5) 0.23178(15) 0.0506(11) Uani d . 1 1 . .
H H18A -0.4324 -0.1724 0.2182 0.076 Uiso calc R 1 1 . .
H H18B -0.3920 -0.0627 0.2599 0.076 Uiso calc R 1 1 . .
H H18C -0.2135 -0.1598 0.2432 0.076 Uiso calc R 1 1 . .
C C19 0.1743(7) 0.1946(4) 0.10400(14) 0.0421(10) Uani d . 1 1 . .
C C20 0.3401(7) 0.2731(5) 0.12998(15) 0.0528(13) Uani d . 1 1 . .
H H20A 0.3255 0.3696 0.1259 0.063 Uiso calc R 1 1 . .
H H20B 0.3571 0.2497 0.1656 0.063 Uiso calc R 1 1 . .
O O21 0.4946(5) 0.2159(3) 0.09772(13) 0.0672(10) Uani d . 1 1 . .
C C22 0.3494(7) 0.1203(5) 0.07878(17) 0.0539(12) Uani d . 1 1 . .
H H22A 0.3701 0.0303 0.0920 0.065 Uiso calc R 1 1 . .
H H22B 0.3400 0.1190 0.0419 0.065 Uiso calc R 1 1 . .
C C23 0.0478(7) 0.2774(5) 0.06772(15) 0.0472(12) Uani d . 1 1 . .
H H23A -0.0318 0.2179 0.0460 0.057 Uiso calc R 1 1 . .
H H23B -0.0486 0.3322 0.0869 0.057 Uiso calc R 1 1 . .
C C24 0.1729(8) 0.3629(5) 0.03667(16) 0.0484(12) Uani d . 1 1 . .
N N25 0.2739(7) 0.4295(4) 0.01284(15) 0.0658(12) Uani d . 1 1 . .
O O1L 0.0901(13) 0.1801(9) 0.5242(3) 0.077(2) Uani d P 0.48 1 A 1
H H1L1 0.1783 0.2403 0.5036 0.115 Uiso d PR 0.48 1 A 1
H H1L2 0.1406 0.1662 0.5525 0.115 Uiso d PR 0.48 1 A 1
O O2L 0.1719(14) 0.2748(9) 0.5074(2) 0.085(2) Uani d P 0.52 1 B 2
H H2L1 0.0459 0.2619 0.5042 0.128 Uiso d PR 0.52 1 B 2
H H2L2 0.1751 0.3371 0.5283 0.128 Uiso d PR 0.52 1 B 2
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
N1 0.062(3) 0.052(3) 0.0307(18) -0.009(2) -0.0069(18) 0.0009(18)
C2 0.048(3) 0.051(3) 0.047(3) 0.001(2) 0.002(2) -0.001(2)
C3 0.049(3) 0.044(3) 0.038(2) -0.002(2) -0.001(2) 0.002(2)
C4 0.049(3) 0.041(3) 0.037(2) -0.006(2) -0.002(2) 0.0023(19)
C5 0.053(3) 0.033(2) 0.032(2) -0.003(2) 0.0015(19) -0.0006(19)
N6 0.046(2) 0.052(2) 0.0373(19) 0.0060(19) 0.0052(17) -0.0011(17)
C7 0.056(3) 0.050(3) 0.037(2) 0.002(2) 0.005(2) 0.000(2)
N8 0.059(3) 0.048(2) 0.0340(18) -0.004(2) 0.0029(19) -0.0006(16)
C9 0.052(3) 0.039(3) 0.032(2) -0.004(2) 0.001(2) 0.0042(19)
N10 0.041(2) 0.047(2) 0.0304(17) 0.0066(18) 0.0005(15) -0.0002(16)
C11 0.046(3) 0.051(3) 0.038(2) 0.006(2) 0.003(2) 0.001(2)
C12 0.044(3) 0.043(3) 0.037(2) 0.005(2) -0.003(2) 0.001(2)
C13 0.048(3) 0.047(3) 0.031(2) 0.008(2) -0.0015(19) -0.001(2)
N14 0.050(2) 0.037(2) 0.0333(17) 0.0038(19) -0.0005(16) -0.0040(16)
C15 0.055(3) 0.038(3) 0.039(2) 0.000(2) -0.003(2) -0.005(2)
C16 0.059(3) 0.042(3) 0.041(2) -0.001(2) -0.002(2) 0.002(2)
C17 0.046(3) 0.042(3) 0.040(2) 0.002(2) -0.001(2) 0.001(2)
C18 0.053(3) 0.055(3) 0.044(2) 0.001(3) -0.007(2) 0.006(2)
C19 0.044(3) 0.047(3) 0.035(2) -0.005(2) -0.002(2) 0.003(2)
C20 0.050(3) 0.061(3) 0.048(3) -0.004(3) 0.000(2) -0.002(2)
O21 0.045(2) 0.081(3) 0.076(2) -0.002(2) 0.0006(18) -0.005(2)
C22 0.054(3) 0.055(3) 0.052(3) 0.010(3) 0.009(2) 0.002(2)
C23 0.051(3) 0.051(3) 0.040(2) -0.001(2) -0.001(2) 0.012(2)
C24 0.060(3) 0.048(3) 0.037(2) 0.013(3) 0.002(2) -0.004(2)
N25 0.084(3) 0.059(3) 0.054(2) -0.003(2) 0.014(2) 0.006(2)
O1L 0.113(7) 0.072(6) 0.045(4) 0.005(5) -0.013(4) 0.001(4)
O2L 0.130(7) 0.078(6) 0.049(4) 0.010(5) -0.020(5) -0.024(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
N1 C9 . 1.351(5) ?
N1 C2 . 1.381(5) ?
N1 H1 . 0.8800 ?
C2 C3 . 1.356(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.452(6) ?
C3 H3 . 0.9500 ?
C4 C9 . 1.378(5) ?
C4 C5 . 1.410(6) ?
C5 N10 . 1.352(5) ?
C5 N6 . 1.359(5) ?
N6 C7 . 1.323(5) ?
C7 N8 . 1.312(5) ?
C7 H7 . 0.9500 ?
N8 C9 . 1.369(6) ?
N10 C12 . 1.467(5) ?
N10 C11 . 1.476(5) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.521(6) ?
C12 C17 . 1.538(6) ?
C12 H12 . 1.0000 ?
C13 N14 . 1.463(5) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
N14 C19 . 1.445(5) ?
N14 C15 . 1.458(5) ?
C15 C16 . 1.520(6) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.524(6) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.519(6) ?
C17 H17 . 1.0000 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 C20 . 1.523(6) ?
C19 C23 . 1.534(6) ?
C19 C22 . 1.538(6) ?
C20 O21 . 1.458(5) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
O21 C22 . 1.456(6) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.459(7) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 N25 . 1.145(6) ?
O1L H1L1 . 1.0100 ?
O1L H1L2 . 0.8390 ?
O1L H2L1 . 1.0319 ?
O2L H1L1 . 0.3669 ?
O2L H2L1 . 0.8478 ?
O2L H2L2 . 0.8441 ?
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
C9 N1 C2 . . 108.3(3) ?
C9 N1 H1 . . 125.8 ?
C2 N1 H1 . . 125.8 ?
C3 C2 N1 . . 109.2(4) ?
C3 C2 H2 . . 125.4 ?
N1 C2 H2 . . 125.4 ?
C2 C3 C4 . . 107.1(4) ?
C2 C3 H3 . . 126.4 ?
C4 C3 H3 . . 126.4 ?
C9 C4 C5 . . 115.8(4) ?
C9 C4 C3 . . 105.3(4) ?
C5 C4 C3 . . 138.7(4) ?
N10 C5 N6 . . 116.0(4) ?
N10 C5 C4 . . 125.3(4) ?
N6 C5 C4 . . 118.6(4) ?
C7 N6 C5 . . 118.1(4) ?
N8 C7 N6 . . 130.0(4) ?
N8 C7 H7 . . 115.0 ?
N6 C7 H7 . . 115.0 ?
C7 N8 C9 . . 110.8(4) ?
N1 C9 N8 . . 123.3(4) ?
N1 C9 C4 . . 110.1(4) ?
N8 C9 C4 . . 126.5(4) ?
C5 N10 C12 . . 121.8(3) ?
C5 N10 C11 . . 118.8(3) ?
C12 N10 C11 . . 119.4(3) ?
N10 C11 H11A . . 109.5 ?
N10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N10 C12 C13 . . 114.1(3) ?
N10 C12 C17 . . 114.3(3) ?
C13 C12 C17 . . 110.9(3) ?
N10 C12 H12 . . 105.5 ?
C13 C12 H12 . . 105.5 ?
C17 C12 H12 . . 105.5 ?
N14 C13 C12 . . 112.9(4) ?
N14 C13 H13A . . 109.0 ?
C12 C13 H13A . . 109.0 ?
N14 C13 H13B . . 109.0 ?
C12 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C19 N14 C15 . . 114.1(3) ?
C19 N14 C13 . . 113.0(3) ?
C15 N14 C13 . . 109.8(3) ?
N14 C15 C16 . . 108.8(3) ?
N14 C15 H15A . . 109.9 ?
C16 C15 H15A . . 109.9 ?
N14 C15 H15B . . 109.9 ?
C16 C15 H15B . . 109.9 ?
H15A C15 H15B . . 108.3 ?
C15 C16 C17 . . 112.0(4) ?
C15 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
C15 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C18 C17 C16 . . 111.0(4) ?
C18 C17 C12 . . 112.2(3) ?
C16 C17 C12 . . 112.6(4) ?
C18 C17 H17 . . 106.9 ?
C16 C17 H17 . . 106.9 ?
C12 C17 H17 . . 106.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N14 C19 C20 . . 113.7(3) ?
N14 C19 C23 . . 114.2(4) ?
C20 C19 C23 . . 113.3(4) ?
N14 C19 C22 . . 113.6(4) ?
C20 C19 C22 . . 85.2(3) ?
C23 C19 C22 . . 113.6(3) ?
O21 C20 C19 . . 91.4(3) ?
O21 C20 H20A . . 113.4 ?
C19 C20 H20A . . 113.4 ?
O21 C20 H20B . . 113.4 ?
C19 C20 H20B . . 113.4 ?
H20A C20 H20B . . 110.7 ?
C22 O21 C20 . . 90.6(3) ?
O21 C22 C19 . . 90.9(3) ?
O21 C22 H22A . . 113.5 ?
C19 C22 H22A . . 113.5 ?
O21 C22 H22B . . 113.5 ?
C19 C22 H22B . . 113.5 ?
H22A C22 H22B . . 110.8 ?
C24 C23 C19 . . 112.2(4) ?
C24 C23 H23A . . 109.2 ?
C19 C23 H23A . . 109.2 ?
C24 C23 H23B . . 109.2 ?
C19 C23 H23B . . 109.2 ?
H23A C23 H23B . . 107.9 ?
N25 C24 C23 . . 178.8(5) ?
H1L1 O1L H1L2 . . 111.5 ?
H1L1 O1L H2L1 . . 52.4 ?
H1L2 O1L H2L1 . . 135.9 ?
H1L1 O2L H2L1 . . 86.4 ?
H1L1 O2L H2L2 . . 153.9 ?
H2L1 O2L H2L2 . . 102.0 ?
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
C9 N1 C2 C3 . . . . -0.2(5) ?
N1 C2 C3 C4 . . . . -0.2(5) ?
C2 C3 C4 C9 . . . . 0.5(5) ?
C2 C3 C4 C5 . . . . 174.8(5) ?
C9 C4 C5 N10 . . . . 174.1(4) ?
C3 C4 C5 N10 . . . . 0.2(8) ?
C9 C4 C5 N6 . . . . -3.7(6) ?
C3 C4 C5 N6 . . . . -177.5(5) ?
N10 C5 N6 C7 . . . . -175.4(4) ?
C4 C5 N6 C7 . . . . 2.6(6) ?
C5 N6 C7 N8 . . . . -0.7(7) ?
N6 C7 N8 C9 . . . . 0.1(7) ?
C2 N1 C9 N8 . . . . -179.3(4) ?
C2 N1 C9 C4 . . . . 0.5(5) ?
C7 N8 C9 N1 . . . . 178.2(4) ?
C7 N8 C9 C4 . . . . -1.5(6) ?
C5 C4 C9 N1 . . . . -176.4(4) ?
C3 C4 C9 N1 . . . . -0.7(5) ?
C5 C4 C9 N8 . . . . 3.3(6) ?
C3 C4 C9 N8 . . . . 179.1(4) ?
N6 C5 N10 C12 . . . . -1.8(6) ?
C4 C5 N10 C12 . . . . -179.6(4) ?
N6 C5 N10 C11 . . . . 178.5(4) ?
C4 C5 N10 C11 . . . . 0.6(6) ?
C5 N10 C12 C13 . . . . 125.6(4) ?
C11 N10 C12 C13 . . . . -54.6(5) ?
C5 N10 C12 C17 . . . . -105.3(4) ?
C11 N10 C12 C17 . . . . 74.5(5) ?
N10 C12 C13 N14 . . . . 79.8(4) ?
C17 C12 C13 N14 . . . . -51.0(5) ?
C12 C13 N14 C19 . . . . -169.0(3) ?
C12 C13 N14 C15 . . . . 62.3(4) ?
C19 N14 C15 C16 . . . . 167.6(4) ?
C13 N14 C15 C16 . . . . -64.4(4) ?
N14 C15 C16 C17 . . . . 58.3(5) ?
C15 C16 C17 C18 . . . . -175.4(4) ?
C15 C16 C17 C12 . . . . -48.6(5) ?
N10 C12 C17 C18 . . . . 39.5(5) ?
C13 C12 C17 C18 . . . . 170.1(4) ?
N10 C12 C17 C16 . . . . -86.7(4) ?
C13 C12 C17 C16 . . . . 44.0(5) ?
C15 N14 C19 C20 . . . . -166.0(4) ?
C13 N14 C19 C20 . . . . 67.7(5) ?
C15 N14 C19 C23 . . . . 61.8(5) ?
C13 N14 C19 C23 . . . . -64.6(5) ?
C15 N14 C19 C22 . . . . -70.7(5) ?
C13 N14 C19 C22 . . . . 162.9(3) ?
N14 C19 C20 O21 . . . . 123.8(4) ?
C23 C19 C20 O21 . . . . -103.5(4) ?
C22 C19 C20 O21 . . . . 10.2(3) ?
C19 C20 O21 C22 . . . . -10.7(3) ?
C20 O21 C22 C19 . . . . 10.6(3) ?
N14 C19 C22 O21 . . . . -124.0(4) ?
C20 C19 C22 O21 . . . . -10.2(3) ?
C23 C19 C22 O21 . . . . 103.2(4) ?
N14 C19 C23 C24 . . . . 176.8(4) ?
C20 C19 C23 C24 . . . . 44.4(5) ?
C22 C19 C23 C24 . . . . -50.7(5) ?
C19 C23 C24 N25 . . . . -1E1(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
N1 H1 O1L . 0.88 1.90 2.783(8) 178
N1 H1 O2L . 0.88 2.06 2.816(7) 144
O1L H1L2 N8 3_556 0.84 2.27 2.868(8) 129
O2L H2L2 N8 3_556 0.84 2.20 2.733(7) 121
O2L H2L2 N25 2_565 0.84 2.43 3.026(10) 129
_iucr_refine_instructions_details
;
TITL mg2443 in P 21 21 21
CELL 0.71073 6.6088 10.1483 26.8134 90.000 90.000 90.000
ZERR 4 0.0006 0.0008 0.0021 0.000 0.000 0.000
REM Gitterkonstanten aus 6886 Reflexen mit 2.5-27.8 Grad V=1798.3(3)
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 72 104 24 8
OMIT -2 56
L.S. 4
FMAP 2
PLAN -25 .5 -.5
TEMP -80
EQIV $1 x+0.5, -y+0.5, -z+1
EQIV $2 -x+0.5, -y+1, z+0.5
EQIV $3 x-0.5, -y+0.5, -z+1
ACTA
CONF
BOND $H
SIZE 0.06 0.27 0.29
HTAB N1 O1L
HTAB N1 O2L
HTAB O1L N8_$1
HTAB O2L N8_$1
HTAB O2L N25_$2
WGHT 0.052300
FVAR 0.70676
MOLE 1
N1 3 0.128033 0.106174 0.424716 11.00000 0.06248 0.05217 =
0.03071 0.00092 -0.00688 -0.00948
0.00055 0.00038 0.00012 0.00252 0.00259 0.00177 0.00176 0.00177 0.00212
AFIX 43
H1 2 0.115970 0.127585 0.456380 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C2 1 0.291860 0.043326 0.403322 11.00000 0.04783 0.05083 =
0.04697 -0.00110 0.00164 0.00092
0.00070 0.00044 0.00016 0.00308 0.00306 0.00251 0.00221 0.00222 0.00235
AFIX 43
H2 2 0.410562 0.016261 0.420480 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C3 1 0.256266 0.026413 0.353929 11.00000 0.04934 0.04409 =
0.03823 0.00156 -0.00086 -0.00173
0.00067 0.00044 0.00015 0.00272 0.00283 0.00226 0.00201 0.00206 0.00227
AFIX 43
H3 2 0.344555 -0.013856 0.330488 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C4 1 0.057873 0.081416 0.343612 11.00000 0.04852 0.04101 =
0.03741 0.00229 -0.00217 -0.00592
0.00068 0.00043 0.00015 0.00274 0.00284 0.00225 0.00195 0.00202 0.00224
C5 1 -0.067959 0.106018 0.302168 11.00000 0.05258 0.03308 =
0.03170 -0.00063 0.00146 -0.00272
0.00067 0.00042 0.00014 0.00285 0.00241 0.00209 0.00188 0.00195 0.00222
N6 3 -0.248596 0.166701 0.309834 11.00000 0.04590 0.05161 =
0.03733 -0.00113 0.00521 0.00601
0.00056 0.00035 0.00012 0.00221 0.00248 0.00188 0.00170 0.00170 0.00192
C7 1 -0.294123 0.204382 0.355727 11.00000 0.05606 0.04966 =
0.03716 -0.00025 0.00451 0.00207
0.00071 0.00044 0.00015 0.00296 0.00297 0.00226 0.00208 0.00231 0.00243
AFIX 43
H7 2 -0.421130 0.247288 0.359139 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
N8 3 -0.190862 0.191618 0.397258 11.00000 0.05901 0.04804 =
0.03397 -0.00061 0.00289 -0.00388
0.00060 0.00038 0.00012 0.00265 0.00237 0.00178 0.00164 0.00187 0.00210
C9 1 -0.010545 0.129149 0.388688 11.00000 0.05226 0.03911 =
0.03244 0.00422 0.00078 -0.00428
0.00069 0.00041 0.00014 0.00288 0.00252 0.00214 0.00186 0.00216 0.00234
N10 3 -0.021554 0.077821 0.254228 11.00000 0.04142 0.04705 =
0.03043 -0.00023 0.00051 0.00657
0.00049 0.00032 0.00011 0.00201 0.00207 0.00166 0.00156 0.00154 0.00185
C11 1 0.174794 0.014975 0.243204 11.00000 0.04617 0.05100 =
0.03822 0.00063 0.00287 0.00568
0.00061 0.00044 0.00014 0.00260 0.00278 0.00217 0.00200 0.00207 0.00231
AFIX 137
H11A 2 0.188513 0.002876 0.207101 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
H11B 2 0.181527 -0.070929 0.259817 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
H11C 2 0.284726 0.071244 0.255374 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C12 1 -0.161007 0.107540 0.213165 11.00000 0.04396 0.04337 =
0.03725 0.00088 -0.00342 0.00459
0.00065 0.00044 0.00014 0.00256 0.00267 0.00217 0.00198 0.00200 0.00236
AFIX 13
H12 2 -0.269928 0.163383 0.228114 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C13 1 -0.068316 0.190607 0.171828 11.00000 0.04788 0.04678 =
0.03104 -0.00135 -0.00148 0.00821
0.00066 0.00045 0.00013 0.00272 0.00286 0.00198 0.00195 0.00193 0.00232
AFIX 23
H13A 2 -0.178203 0.233914 0.152827 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H13B 2 0.016018 0.260608 0.186968 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
N14 3 0.056190 0.113543 0.137430 11.00000 0.04987 0.03726 =
0.03330 -0.00402 -0.00054 0.00382
0.00051 0.00035 0.00011 0.00219 0.00204 0.00167 0.00159 0.00160 0.00187
C15 1 -0.068373 0.015269 0.112330 11.00000 0.05506 0.03756 =
0.03861 -0.00522 -0.00264 -0.00045
0.00068 0.00042 0.00014 0.00289 0.00261 0.00225 0.00203 0.00212 0.00225
AFIX 23
H15A 2 0.012980 -0.031824 0.086963 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H15B 2 -0.183193 0.058804 0.095276 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C16 1 -0.147191 -0.081787 0.150905 11.00000 0.05910 0.04202 =
0.04099 0.00170 -0.00197 -0.00106
0.00070 0.00043 0.00015 0.00284 0.00288 0.00229 0.00209 0.00219 0.00232
AFIX 23
H16A 2 -0.031429 -0.128399 0.166330 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H16B 2 -0.233120 -0.148276 0.134131 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C17 1 -0.269796 -0.013682 0.191538 11.00000 0.04581 0.04158 =
0.03993 0.00101 -0.00096 0.00228
0.00068 0.00043 0.00014 0.00267 0.00266 0.00219 0.00196 0.00201 0.00216
AFIX 13
H17 2 -0.396986 0.018899 0.175535 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C18 1 -0.332448 -0.110745 0.231784 11.00000 0.05261 0.05517 =
0.04393 0.00554 -0.00715 0.00077
0.00068 0.00047 0.00015 0.00273 0.00297 0.00242 0.00219 0.00218 0.00265
AFIX 137
H18A 2 -0.432357 -0.172395 0.218182 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
H18B 2 -0.391966 -0.062714 0.259893 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
H18C 2 -0.213452 -0.159763 0.243247 11.00000 -1.50000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C19 1 0.174309 0.194575 0.104005 11.00000 0.04442 0.04654 =
0.03521 0.00301 -0.00173 -0.00461
0.00066 0.00045 0.00014 0.00266 0.00272 0.00204 0.00197 0.00211 0.00230
C20 1 0.340128 0.273059 0.129976 11.00000 0.05018 0.06057 =
0.04752 -0.00211 -0.00021 -0.00400
0.00069 0.00050 0.00015 0.00301 0.00348 0.00254 0.00234 0.00243 0.00264
AFIX 23
H20A 2 0.325498 0.369559 0.125942 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H20B 2 0.357112 0.249674 0.165576 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
O21 4 0.494622 0.215902 0.097725 11.00000 0.04494 0.08069 =
0.07588 -0.00542 0.00060 -0.00239
0.00053 0.00035 0.00013 0.00201 0.00251 0.00223 0.00195 0.00181 0.00199
C22 1 0.349370 0.120304 0.078777 11.00000 0.05449 0.05535 =
0.05173 0.00226 0.00933 0.00968
0.00069 0.00050 0.00017 0.00299 0.00312 0.00258 0.00239 0.00239 0.00270
AFIX 23
H22A 2 0.370079 0.030264 0.092038 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H22B 2 0.339977 0.118991 0.041931 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C23 1 0.047753 0.277407 0.067724 11.00000 0.05061 0.05138 =
0.03973 0.01179 -0.00129 -0.00141
0.00069 0.00045 0.00015 0.00299 0.00309 0.00226 0.00210 0.00216 0.00237
AFIX 23
H23A 2 -0.031805 0.217888 0.046015 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
H23B 2 -0.048616 0.332160 0.086949 11.00000 -1.20000
0.00000 0.00000 0.00000 0.00000
AFIX 0
C24 1 0.172909 0.362873 0.036669 11.00000 0.06029 0.04807 =
0.03695 -0.00390 0.00182 0.01319
0.00079 0.00047 0.00016 0.00311 0.00307 0.00229 0.00217 0.00235 0.00251
N25 3 0.273906 0.429468 0.012838 11.00000 0.08392 0.05922 =
0.05433 0.00586 0.01424 -0.00301
0.00071 0.00043 0.00015 0.00327 0.00292 0.00241 0.00217 0.00233 0.00249
PART 1
O1L 4 0.090120 0.180065 0.524220 10.48000 0.11330 0.07183 =
0.04499 0.00051 -0.01318 0.00481
0.00130 0.00089 0.00026 0.00716 0.00598 0.00412 0.00405 0.00429 0.00503
AFIX 3
H1L1 2 0.178266 0.240337 0.503569 10.48000 -1.50000
0.00000 0.00000 0.00000 0.00000
H1L2 2 0.140566 0.166188 0.552450 10.48000 -1.50000
0.00000 0.00000 0.00000 0.00000
AFIX 0
PART 2
O2L 4 0.171919 0.274761 0.507442 10.52000 0.13004 0.07767 =
0.04864 -0.02426 -0.02031 0.00950
0.00137 0.00089 0.00024 0.00740 0.00620 0.00409 0.00392 0.00454 0.00545
AFIX 3
H2L1 2 0.045863 0.261922 0.504165 10.52000 -1.50000
0.00000 0.00000 0.00000 0.00000
H2L2 2 0.175146 0.337137 0.528252 10.52000 -1.50000
0.00000 0.00000 0.00000 0.00000
HKLF 4
END
;
data_Global
_journal_date_recd_electronic 2014-02-24
_journal_date_accepted 2014-02-26
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2014
_journal_volume 70
_journal_issue 4
_journal_page_first o382
_journal_page_last o383
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536814004449
_journal_coeditor_code BT6965
_publ_contact_author_name 'Stefan Laufer'
_publ_contact_author_address
;
Auf der Morgenstelle 8
72076 Tuebingen
Germany
;
_publ_contact_author_email stefan.laufer@uni-tuebingen.de
_publ_contact_author_fax '+49 7071 295037'
_publ_contact_author_phone '+49 7071 2972459'
_publ_section_title
;\
2-(3-{(3R,4R)-4-Methyl-3-[methyl(7H-pyrrolo[2,3-d]\
pyrimidin-4-yl)amino]piperidin-1-yl}oxetan-3-yl)acetonitrile monohydrate
;
loop_
_publ_author_name
_publ_author_address
'Gehringer, Matthias'
;
Eberhard-Karls-University Tuebingen,
Institute of Pharmacy,
Department of Pharmaceutical and Medicinal Chemistry,
Auf der Morgenstelle 8,
72076 Tuebingen,
Germany
;
'Pfaffenrot, Ellen'
;
Eberhard-Karls-University Tuebingen,
Institute of Pharmacy,
Department of Pharmaceutical and Medicinal Chemistry,
Auf der Morgenstelle 8,
72076 Tuebingen,
Germany
;
'Keck, Peter R. W. E. F.'
;
Eberhard-Karls-University Tuebingen,
Institute of Pharmacy,
Department of Pharmaceutical and Medicinal Chemistry,
Auf der Morgenstelle 8,
72076 Tuebingen,
Germany
;
'Schollmeyer, Dieter'
;
University Mainz
Institut of Organic Chemistry
Duesbergweg 10-14
55099 Mainz
Germany
;
'Laufer, Stefan A.'
;
Eberhard-Karls-University Tuebingen,
Institute of Pharmacy,
Department of Pharmaceutical and Medicinal Chemistry,
Auf der Morgenstelle 8,
72076 Tuebingen,
Germany
;