#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/56/1505676.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_1505676
loop_
_publ_author_name
'Harju, Kirsi'
'Kylänlahti, Irene'
'Paananen, Timo'
'Polamo, Mika'
'Nielsen, John'
'Yli-Kauhaluoma, Jari'
_publ_section_title
;
 Solid-Phase Synthesis of Pyrazolopyridines from Polymer-Bound Alkyne and
 Azomethine Imines
;
_journal_issue                   3
_journal_name_full               'Journal of Combinatorial Chemistry'
_journal_page_first              344
_journal_paper_doi               10.1021/cc050138j
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C10 H8 N2 O4'
_chemical_formula_weight         220.18
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9450(10)
_cell_length_b                   10.887(2)
_cell_length_c                   18.475(4)
_cell_measurement_temperature    173(2)
_cell_volume                     988.6(3)
_computing_cell_refinement       'COLLECT (Nonius, 2002)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'COLLECT (Nonius, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_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  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15484
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0811P)²+1.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.1983
_reflns_number_gt                1667
_reflns_number_total             2272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cc050138jsi20060308_034221.cif
_cod_data_source_block           6e
_cod_original_sg_symbol_H-M      'P  2(1)/c '
_cod_database_code               1505676
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_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
N1 N -0.2766(5) 0.0311(2) 0.19671(13) 0.0283(6) Uani 1 1 d .
N2 N -0.2370(4) 0.1541(2) 0.18703(12) 0.0238(5) Uani 1 1 d .
C3 C -0.3742(6) 0.2443(3) 0.22027(15) 0.0281(7) Uani 1 1 d .
H3 H -0.5003 0.2240 0.2521 0.034 Uiso 1 1 calc R
C4 C -0.3219(6) 0.3635(3) 0.20565(15) 0.0285(6) Uani 1 1 d .
H4 H -0.4135 0.4258 0.2273 0.034 Uiso 1 1 calc R
C5 C -0.1265(6) 0.3934(3) 0.15713(15) 0.0265(6) Uani 1 1 d .
C6 C -0.0754(6) 0.5258(3) 0.14191(16) 0.0304(7) Uani 1 1 d .
O7 O -0.1854(5) 0.61085(19) 0.16927(13) 0.0405(6) Uani 1 1 d .
O8 O 0.1080(5) 0.53930(19) 0.09426(13) 0.0408(6) Uani 1 1 d .
C9 C 0.1700(8) 0.6645(3) 0.0753(2) 0.0447(8) Uani 1 1 d .
H9C H 0.3025 0.6641 0.0411 0.067 Uiso 1 1 calc R
H9B H 0.2414 0.7080 0.1184 0.067 Uiso 1 1 calc R
H9A H 0.0071 0.7042 0.0540 0.067 Uiso 1 1 calc R
C10 C 0.0103(5) 0.3025(3) 0.12461(14) 0.0243(6) Uani 1 1 d .
H10 H 0.1377 0.3225 0.0931 0.029 Uiso 1 1 calc R
C11 C -0.0446(5) 0.1787(2) 0.13962(14) 0.0219(6) Uani 1 1 d .
C12 C 0.0420(5) 0.0630(2) 0.11757(14) 0.0233(6) Uani 1 1 d .
C13 C 0.2404(5) 0.0369(2) 0.06703(15) 0.0224(6) Uani 1 1 d .
O14 O 0.2833(4) -0.07369(18) 0.05004(11) 0.0305(5) Uani 1 1 d .
O15 O 0.3629(4) 0.12899(17) 0.04081(11) 0.0299(5) Uani 1 1 d .
H15 H 0.4694 0.1038 0.0132 0.045 Uiso 1 1 calc R
C16 C -0.1091(6) -0.0217(3) 0.15431(15) 0.0272(6) Uani 1 1 d .
H16 H -0.0934 -0.1063 0.1494 0.033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 N1 N2 103.8(2)
N1 N2 C3 123.8(2)
N1 N2 C11 112.9(2)
C3 N2 C11 123.4(2)
C4 C3 N2 118.7(2)
C4 C3 H3 120.7
N2 C3 H3 120.7
C3 C4 C5 120.1(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C10 C5 C4 120.7(3)
C10 C5 C6 120.7(3)
C4 C5 C6 118.6(3)
O7 C6 O8 123.9(3)
O7 C6 C5 124.4(3)
O8 C6 C5 111.7(2)
C6 O8 C9 116.0(2)
O8 C9 H9C 109.5
O8 C9 H9B 109.5
H9C C9 H9B 109.5
O8 C9 H9A 109.5
H9C C9 H9A 109.5
H9B C9 H9A 109.5
C5 C10 C11 119.2(2)
C5 C10 H10 120.4
C11 C10 H10 120.4
N2 C11 C12 105.2(2)
N2 C11 C10 118.0(2)
C12 C11 C10 136.8(2)
C11 C12 C16 104.6(2)
C11 C12 C13 127.6(2)
C16 C12 C13 127.8(3)
O14 C13 O15 123.1(2)
O14 C13 C12 119.2(2)
O15 C13 C12 117.7(2)
C13 O15 H15 109.5
N1 C16 C12 113.5(3)
N1 C16 H16 123.3
C12 C16 H16 123.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C16 1.332(4)
N1 N2 1.368(3)
N2 C3 1.376(4)
N2 C11 1.388(3)
C3 C4 1.355(4)
C3 H3 0.9300
C4 C5 1.426(4)
C4 H4 0.9300
C5 C10 1.374(4)
C5 C6 1.495(4)
C6 O7 1.212(4)
C6 O8 1.340(4)
O8 C9 1.448(4)
C9 H9C 0.9600
C9 H9B 0.9600
C9 H9A 0.9600
C10 C11 1.409(4)
C10 H10 0.9300
C11 C12 1.405(4)
C12 C16 1.407(4)
C12 C13 1.455(4)
C13 O14 1.268(3)
C13 O15 1.293(3)
O15 H15 0.8200
C16 H16 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651668 ChemSpider
