#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/41/4024136.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_4024136
loop_
_publ_author_name
'Nicolas Joubert'
'Radek Pohl'
'Blanka Klepetářová'
'Michal Hocek'
_publ_section_title
;
 Modular and Practical Synthesis of 6-Substituted Pyridin-3-yl C-Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6797
_journal_page_last               6805
_journal_paper_doi               10.1021/jo0709504
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H18 N2 O3'
_chemical_formula_sum            'C12 H18 N2 O3'
_chemical_formula_weight         238.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-03-29
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6723(1)
_cell_length_b                   10.6767(1)
_cell_length_c                   19.4350(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     1177.01(2)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17723
_diffrn_reflns_theta_full        68.115
_diffrn_reflns_theta_max         76.534
_diffrn_reflns_theta_min         4.550
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 973 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       64(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000168
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.89 1.44 0.941 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0440
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0374
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                1947
_reflns_number_total             2401
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.28
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_scale          6.620(15)
_oxford_structure_analysis_title 'ABS in P2(1)2(1)2(1)'
_cod_data_source_file            jo0709504-File004.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4024136
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O11 O 0.7175(2) 0.76373(12) 0.15328(6) 0.0253 1.0000 Uani . . . . . .
O13 O 0.9017(2) 0.59207(13) -0.00025(6) 0.0286 1.0000 Uani . . . . . .
O14 O 1.2549(2) 0.80493(12) 0.12537(6) 0.0259 1.0000 Uani . . . . . .
N1 N 0.3684(3) 0.82415(14) 0.34661(8) 0.0246 1.0000 Uani . . . . . .
N15 N 0.1387(3) 0.69814(14) 0.41623(8) 0.0272 1.0000 Uani . . . . . .
C2 C 0.5411(3) 0.83435(17) 0.29994(9) 0.0235 1.0000 Uani . . . . . .
C3 C 0.6778(3) 0.73681(16) 0.27489(8) 0.0213 1.0000 Uani . . . . . .
C4 C 0.6329(3) 0.61847(17) 0.30357(9) 0.0239 1.0000 Uani . . . . . .
C5 C 0.4583(3) 0.60357(17) 0.35211(9) 0.0241 1.0000 Uani . . . . . .
C6 C 0.3218(3) 0.70854(16) 0.37149(9) 0.0227 1.0000 Uani . . . . . .
C7 C 0.8497(3) 0.76089(17) 0.21777(8) 0.0228 1.0000 Uani . . . . . .
C8 C 1.0407(3) 0.66550(17) 0.20335(9) 0.0246 1.0000 Uani . . . . . .
C9 C 1.1082(3) 0.69647(17) 0.12913(9) 0.0223 1.0000 Uani . . . . . .
C10 C 0.8709(3) 0.73021(16) 0.09672(8) 0.0198 1.0000 Uani . . . . . .
C12 C 0.7592(3) 0.62288(17) 0.05746(9) 0.0242 1.0000 Uani . . . . . .
C16 C -0.0128(3) 0.80409(19) 0.43254(10) 0.0308 1.0000 Uani . . . . . .
C17 C 0.0744(3) 0.57729(19) 0.44508(11) 0.0340 1.0000 Uani . . . . . .
H21 H 0.5752 0.9185 0.2827 0.0266 1.0000 Uiso R . . . . .
H41 H 0.7251 0.5451 0.2894 0.0278 1.0000 Uiso R . . . . .
H51 H 0.4304 0.5210 0.3716 0.0286 1.0000 Uiso R . . . . .
H71 H 0.9208 0.8458 0.2244 0.0259 1.0000 Uiso R . . . . .
H81 H 1.1790 0.6775 0.2341 0.0295 1.0000 Uiso R . . . . .
H82 H 0.9739 0.5784 0.2054 0.0282 1.0000 Uiso R . . . . .
H91 H 1.1849 0.6234 0.1054 0.0262 1.0000 Uiso R . . . . .
H101 H 0.8865 0.8048 0.0636 0.0239 1.0000 Uiso R . . . . .
H121 H 0.7522 0.5491 0.0883 0.0294 1.0000 Uiso R . . . . .
H122 H 0.5969 0.6464 0.0438 0.0290 1.0000 Uiso R . . . . .
H131 H 0.8541 0.6364 -0.0349 0.0447 1.0000 Uiso R . . . . .
H141 H 1.3922 0.7849 0.1394 0.0387 1.0000 Uiso R . . . . .
H161 H -0.1759 0.7757 0.4417 0.0461 1.0000 Uiso R . . . . .
H162 H 0.0444 0.8475 0.4744 0.0470 1.0000 Uiso R . . . . .
H163 H -0.0177 0.8646 0.3929 0.0464 1.0000 Uiso R . . . . .
H171 H -0.0472 0.5899 0.4818 0.0500 1.0000 Uiso R . . . . .
H172 H 0.2121 0.5359 0.4670 0.0493 1.0000 Uiso R . . . . .
H173 H 0.0103 0.5220 0.4087 0.0495 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . O11 . C10 . 109.76(12) yes
C12 . O13 . H131 . 108.1 no
C9 . O14 . H141 . 108.2 no
C2 . N1 . C6 . 117.36(15) yes
C6 . N15 . C16 . 121.80(15) yes
C6 . N15 . C17 . 120.74(16) yes
C16 . N15 . C17 . 117.24(15) yes
N1 . C2 . C3 . 125.85(17) yes
N1 . C2 . H21 . 116.9 no
C3 . C2 . H21 . 117.3 no
C2 . C3 . C4 . 115.77(15) yes
C2 . C3 . C7 . 119.65(15) yes
C4 . C3 . C7 . 124.48(15) yes
C3 . C4 . C5 . 120.43(16) yes
C3 . C4 . H41 . 120.7 no
C5 . C4 . H41 . 118.9 no
C4 . C5 . C6 . 119.01(16) yes
C4 . C5 . H51 . 119.3 no
C6 . C5 . H51 . 121.7 no
C5 . C6 . N15 . 121.62(15) yes
C5 . C6 . N1 . 121.44(15) yes
N15 . C6 . N1 . 116.94(15) yes
C3 . C7 . O11 . 107.77(13) yes
C3 . C7 . C8 . 119.16(15) yes
O11 . C7 . C8 . 102.86(12) yes
C3 . C7 . H71 . 108.8 no
O11 . C7 . H71 . 107.3 no
C8 . C7 . H71 . 110.2 no
C7 . C8 . C9 . 102.04(13) yes
C7 . C8 . H81 . 111.5 no
C9 . C8 . H81 . 110.0 no
C7 . C8 . H82 . 110.2 no
C9 . C8 . H82 . 109.3 no
H81 . C8 . H82 . 113.1 no
C8 . C9 . O14 . 111.70(14) yes
C8 . C9 . C10 . 102.67(13) yes
O14 . C9 . C10 . 107.52(13) yes
C8 . C9 . H91 . 111.9 no
O14 . C9 . H91 . 110.7 no
C10 . C9 . H91 . 112.0 no
C9 . C10 . O11 . 105.93(12) yes
C9 . C10 . C12 . 113.40(14) yes
O11 . C10 . C12 . 108.56(13) yes
C9 . C10 . H101 . 111.4 no
O11 . C10 . H101 . 109.6 no
C12 . C10 . H101 . 107.9 no
C10 . C12 . O13 . 109.56(13) yes
C10 . C12 . H121 . 108.3 no
O13 . C12 . H121 . 108.4 no
C10 . C12 . H122 . 109.4 no
O13 . C12 . H122 . 112.1 no
H121 . C12 . H122 . 109.1 no
N15 . C16 . H161 . 110.7 no
N15 . C16 . H162 . 110.4 no
H161 . C16 . H162 . 107.6 no
N15 . C16 . H163 . 110.4 no
H161 . C16 . H163 . 108.0 no
H162 . C16 . H163 . 109.7 no
N15 . C17 . H171 . 109.2 no
N15 . C17 . H172 . 111.3 no
H171 . C17 . H172 . 107.1 no
N15 . C17 . H173 . 110.3 no
H171 . C17 . H173 . 109.6 no
H172 . C17 . H173 . 109.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 . C7 . 1.4607(18) yes
O11 . C10 . 1.4469(18) yes
O13 . C12 . 1.421(2) yes
O13 . H131 . 0.866 no
O14 . C9 . 1.428(2) yes
O14 . H141 . 0.852 no
N1 . C2 . 1.339(2) yes
N1 . C6 . 1.352(2) yes
N15 . C6 . 1.359(2) yes
N15 . C16 . 1.456(2) yes
N15 . C17 . 1.453(2) yes
C2 . C3 . 1.387(2) yes
C2 . H21 . 0.978 no
C3 . C4 . 1.404(2) yes
C3 . C7 . 1.500(2) yes
C4 . C5 . 1.377(2) yes
C4 . H41 . 0.981 no
C5 . C6 . 1.413(2) yes
C5 . H51 . 0.972 no
C7 . C8 . 1.513(2) yes
C7 . H71 . 1.001 no
C8 . C9 . 1.529(2) yes
C8 . H81 . 0.995 no
C8 . H82 . 1.005 no
C9 . C10 . 1.529(2) yes
C9 . H91 . 1.005 no
C10 . C12 . 1.515(2) yes
C10 . H101 . 1.027 no
C12 . H121 . 0.990 no
C12 . H122 . 0.991 no
C16 . H161 . 0.990 no
C16 . H162 . 0.991 no
C16 . H163 . 1.005 no
C17 . H171 . 1.002 no
C17 . H172 . 0.993 no
C17 . H173 . 0.990 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O13 . H131 . O14 2_465 165 0.87 1.95 2.796(2) yes
O14 . H141 . O11 1_655 167 0.85 1.88 2.715(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658839
