#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025863.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_4025863
loop_
_publ_author_name
'Larissa B. Krasnova'
'Jason E. Hein'
'Valery V. Fokin'
_publ_section_title
;
 Synthesis of 7-Aza-5-deazapurine Analogues via Copper(I)-Catalyzed
 Hydroamination of Alkynes and 1-Iodoalkynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8662
_journal_page_last               8665
_journal_paper_doi               10.1021/jo1016376
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C15 H19 N5 O4 S'
_chemical_formula_weight         365.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.5439(17)
_cell_length_b                   8.3721(8)
_cell_length_c                   21.282(2)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.21
_cell_volume                     3304.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22999
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9387
_exptl_absorpt_correction_T_min  0.9263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0362
_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)+(0.0474P)²+3.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2797
_reflns_number_total             3014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1016376_si_002.cif
_cod_data_source_block           sharp20
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3304.0(5)
_cod_database_code               4025863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'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
S1 S -0.20328(2) 0.15970(5) 0.54332(2) 0.01545(14) Uani 1 1 d . . .
O1 O -0.21066(7) 0.07882(15) 0.60196(6) 0.0235(3) Uani 1 1 d . . .
O2 O -0.26621(7) 0.21465(15) 0.51156(6) 0.0236(3) Uani 1 1 d . . .
O3 O -0.01216(7) 0.75263(15) 0.53418(6) 0.0224(3) Uani 1 1 d . . .
O4 O 0.00518(8) 0.94957(17) 0.39723(7) 0.0268(3) Uani 1 1 d . . .
H2S H 0.0056(14) 1.034(3) 0.4217(12) 0.040 Uiso 1 1 d . . .
H1S H -0.0192(14) 0.879(3) 0.4177(12) 0.040 Uiso 1 1 d . . .
N1 N -0.15233(8) 0.31833(17) 0.56032(7) 0.0169(3) Uani 1 1 d . . .
N2 N -0.08576(8) 0.53582(17) 0.54593(6) 0.0153(3) Uani 1 1 d . . .
N3 N -0.15104(8) 0.43390(17) 0.45929(7) 0.0159(3) Uani 1 1 d . . .
N4 N -0.07699(8) 0.67036(17) 0.44917(7) 0.0165(3) Uani 1 1 d . . .
N5 N -0.14795(8) 0.57913(17) 0.36787(7) 0.0172(3) Uani 1 1 d . . .
C1 C -0.15029(10) 0.0485(2) 0.49139(8) 0.0200(4) Uani 1 1 d . . .
H1A H -0.1764 -0.0481 0.4789 0.030 Uiso 1 1 calc R . .
H1B H -0.1051 0.0184 0.5121 0.030 Uiso 1 1 calc R . .
H1C H -0.1396 0.1128 0.4541 0.030 Uiso 1 1 calc R . .
C2 C -0.11945(10) 0.3471(2) 0.62223(8) 0.0199(4) Uani 1 1 d . . .
H2A H -0.0872 0.2582 0.6345 0.024 Uiso 1 1 calc R . .
H2B H -0.1567 0.3620 0.6551 0.024 Uiso 1 1 calc R . .
C3 C -0.07730(9) 0.4997(2) 0.61110(8) 0.0172(4) Uani 1 1 d . . .
C4 C -0.04243(10) 0.5843(2) 0.65358(9) 0.0238(4) Uani 1 1 d . . .
H4A H -0.0194 0.6812 0.6419 0.029 Uiso 1 1 calc R . .
H4B H -0.0403 0.5483 0.6959 0.029 Uiso 1 1 calc R . .
C5 C -0.13106(9) 0.43006(19) 0.51733(8) 0.0144(3) Uani 1 1 d . . .
C6 C -0.05552(9) 0.66053(19) 0.50970(8) 0.0166(4) Uani 1 1 d . . .
C7 C -0.12416(9) 0.56270(19) 0.42694(8) 0.0153(4) Uani 1 1 d . . .
C8 C -0.11954(11) 0.7039(2) 0.32711(9) 0.0236(4) Uani 1 1 d . . .
H8A H -0.0818 0.7631 0.3494 0.035 Uiso 1 1 calc R . .
H8B H -0.1585 0.7772 0.3154 0.035 Uiso 1 1 calc R . .
H8C H -0.0992 0.6554 0.2891 0.035 Uiso 1 1 calc R . .
C9 C -0.20565(9) 0.4775(2) 0.34214(8) 0.0173(4) Uani 1 1 d . . .
H9A H -0.2400 0.5453 0.3185 0.021 Uiso 1 1 calc R . .
H9B H -0.2323 0.4277 0.3774 0.021 Uiso 1 1 calc R . .
C10 C -0.17784(10) 0.34716(19) 0.29911(8) 0.0160(4) Uani 1 1 d . . .
C11 C -0.20612(10) 0.3272(2) 0.23917(8) 0.0177(4) Uani 1 1 d . . .
H11A H -0.2427 0.3972 0.2245 0.021 Uiso 1 1 calc R . .
C12 C -0.18105(10) 0.2050(2) 0.20048(8) 0.0206(4) Uani 1 1 d . . .
H12A H -0.2009 0.1915 0.1597 0.025 Uiso 1 1 calc R . .
C13 C -0.12723(10) 0.1030(2) 0.22122(9) 0.0205(4) Uani 1 1 d . . .
H13A H -0.1100 0.0201 0.1947 0.025 Uiso 1 1 calc R . .
C14 C -0.09860(10) 0.1225(2) 0.28094(9) 0.0199(4) Uani 1 1 d . . .
H14A H -0.0615 0.0532 0.2952 0.024 Uiso 1 1 calc R . .
C15 C -0.12387(9) 0.2430(2) 0.32005(8) 0.0173(4) Uani 1 1 d . . .
H15A H -0.1045 0.2547 0.3611 0.021 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
O2 S1 O1 119.32(8) . . ?
O2 S1 N1 108.03(8) . . ?
O1 S1 N1 104.02(8) . . ?
O2 S1 C1 109.43(9) . . ?
O1 S1 C1 110.75(8) . . ?
N1 S1 C1 104.04(8) . . ?
C5 N1 C2 111.57(14) . . ?
C5 N1 S1 124.24(12) . . ?
C2 N1 S1 123.97(12) . . ?
C5 N2 C6 118.71(14) . . ?
C5 N2 C3 111.32(14) . . ?
C6 N2 C3 129.97(15) . . ?
C5 N3 C7 113.30(15) . . ?
C7 N4 C6 119.17(15) . . ?
C7 N5 C8 120.89(15) . . ?
C7 N5 C9 121.93(14) . . ?
C8 N5 C9 117.12(14) . . ?
N1 C2 C3 102.22(14) . . ?
C4 C3 N2 127.33(17) . . ?
C4 C3 C2 126.76(17) . . ?
N2 C3 C2 105.87(14) . . ?
N3 C5 N2 126.01(16) . . ?
N3 C5 N1 125.12(16) . . ?
N2 C5 N1 108.87(14) . . ?
O3 C6 N4 123.95(16) . . ?
O3 C6 N2 119.43(16) . . ?
N4 C6 N2 116.63(15) . . ?
N5 C7 N4 118.46(15) . . ?
N5 C7 N3 115.58(15) . . ?
N4 C7 N3 125.96(16) . . ?
N5 C9 C10 113.18(14) . . ?
C11 C10 C15 119.14(16) . . ?
C11 C10 C9 120.89(16) . . ?
C15 C10 C9 119.97(15) . . ?
C10 C11 C12 120.35(16) . . ?
C13 C12 C11 120.31(17) . . ?
C12 C13 C14 119.65(17) . . ?
C13 C14 C15 120.37(17) . . ?
C14 C15 C10 120.17(16) . . ?
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
S1 O2 1.4249(13) . ?
S1 O1 1.4265(13) . ?
S1 N1 1.6696(15) . ?
S1 C1 1.7475(17) . ?
O3 C6 1.230(2) . ?
N1 C5 1.367(2) . ?
N1 C2 1.472(2) . ?
N2 C5 1.364(2) . ?
N2 C6 1.414(2) . ?
N2 C3 1.428(2) . ?
N3 C5 1.290(2) . ?
N3 C7 1.373(2) . ?
N4 C7 1.342(2) . ?
N4 C6 1.351(2) . ?
N5 C7 1.339(2) . ?
N5 C8 1.457(2) . ?
N5 C9 1.473(2) . ?
C2 C3 1.516(2) . ?
C3 C4 1.318(3) . ?
C9 C10 1.515(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.393(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.389(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H2S O3 0.88(3) 2.02(3) 2.8921(19) 171(2) 5_576
O4 H1S N4 0.86(3) 2.15(3) 3.001(2) 167(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659319
