#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513597.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_1513597
loop_
_publ_author_name
'Pradhan, Koyel'
'Paul, Sanjay'
'Das, Asish R.'
_publ_section_title
;
 Magnetically retrievable nano crystalline CuFe2O4 catalyzed
 multi-component reaction: a facile and efficient synthesis of
 functionalized dihydropyrano[2,3-c]pyrazole, pyrano[3,2-c]coumarin and
 4H-chromene derivatives in aqueous media
;
_journal_issue                   3
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              822
_journal_paper_doi               10.1039/c3cy00901g
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C13 H14 N4 O5'
_chemical_formula_weight         306.2774
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.34(2)
_cell_angle_beta                 89.43(2)
_cell_angle_gamma                80.99(2)
_cell_formula_units_Z            2
_cell_length_a                   8.964(4)
_cell_length_b                   9.189(4)
_cell_length_c                   11.432(5)
_cell_measurement_temperature    293(2)
_cell_volume                     869.2(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.126
_diffrn_measured_fraction_theta_max 0.939
_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  0.0827
_diffrn_reflns_av_sigmaI/netI    0.1175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7532
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0986
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2769
_refine_ls_wR_factor_ref         0.3321
_reflns_number_gt                2042
_reflns_number_total             3903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cy00901g.txt
_cod_data_source_block           heme6_0m
_cod_database_code               1513597
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.5733(3) 0.4313(3) 0.13679(19) 0.0569(7) Uani 1 1 d .
O4 O 0.7063(4) 0.5454(4) 0.4032(3) 0.0882(10) Uani 1 1 d .
N3 N 0.8567(4) 0.6396(3) 0.0316(2) 0.0523(8) Uani 1 1 d .
C1 C 0.8199(4) 0.3404(4) 0.3366(3) 0.0473(8) Uani 1 1 d .
O3 O 0.9199(4) 0.0061(4) 0.3181(3) 0.0807(10) Uani 1 1 d .
N4 N 0.4428(4) 0.2517(4) 0.2485(3) 0.0608(9) Uani 1 1 d .
C5 C 0.8210(4) 0.4592(3) 0.2072(3) 0.0454(8) Uani 1 1 d .
C2 C 0.6801(4) 0.2645(3) 0.3412(2) 0.0456(8) Uani 1 1 d .
C7 C 1.0749(5) 0.5721(4) 0.1831(3) 0.0599(10) Uani 1 1 d .
H7A H 1.1129 0.6516 0.1154 0.090 Uiso 1 1 calc R
H7B H 1.1419 0.4735 0.2022 0.090 Uiso 1 1 calc R
H7C H 1.0688 0.6022 0.2555 0.090 Uiso 1 1 calc R
N2 N 0.7197(4) 0.6067(3) 0.0113(2) 0.0560(8) Uani 1 1 d .
C12 C 0.9655(5) 0.2164(4) 0.3714(3) 0.0611(10) Uani 1 1 d .
H12A H 1.0517 0.2688 0.3705 0.073 Uiso 1 1 calc R
H12B H 0.9599 0.1424 0.4557 0.073 Uiso 1 1 calc R
C8 C 0.6655(4) 0.1357(4) 0.4505(3) 0.0542(9) Uani 1 1 d .
C6 C 0.9224(4) 0.5550(4) 0.1461(3) 0.0479(8) Uani 1 1 d .
N6 N 0.6564(4) 0.0318(4) 0.5416(3) 0.0774(12) Uani 1 1 d .
C3 C 0.5686(4) 0.3106(4) 0.2475(3) 0.0478(8) Uani 1 1 d .
C10 C 0.8073(5) 0.4189(4) 0.4343(3) 0.0579(10) Uani 1 1 d .
O5 O 0.8763(8) 0.3717(6) 0.5308(4) 0.153(2) Uani 1 1 d .
C4 C 0.7009(4) 0.4967(4) 0.1189(3) 0.0478(8) Uani 1 1 d .
O2 O 1.0622(7) 0.1664(4) 0.1949(4) 0.143(2) Uani 1 1 d .
C13 C 0.9885(5) 0.1296(4) 0.2848(3) 0.0703(12) Uani 1 1 d .
C11 C 0.6771(8) 0.6268(8) 0.4887(5) 0.1031(18) Uani 1 1 d .
H11A H 0.5999 0.7172 0.4526 0.155 Uiso 1 1 calc R
H11B H 0.7679 0.6605 0.5057 0.155 Uiso 1 1 calc R
H11C H 0.6437 0.5577 0.5652 0.155 Uiso 1 1 calc R
C14 C 0.9304(12) -0.0807(8) 0.2353(6) 0.137(3) Uani 1 1 d .
H14A H 0.8773 -0.1685 0.2682 0.206 Uiso 1 1 calc R
H14B H 1.0348 -0.1186 0.2277 0.206 Uiso 1 1 calc R
H14C H 0.8862 -0.0133 0.1545 0.206 Uiso 1 1 calc R
C96 C 0.4135(17) -0.1877(17) 0.1863(15) 0.202(6) Uani 1 1 d .
C92 C 0.317(4) -0.115(3) 0.033(3) 0.324(15) Uani 1 1 d .
C94 C 0.5000 0.0000 0.0000 0.098(2) Uani 1 2 d S
C95 C 0.489(4) -0.084(2) 0.093(2) 0.327(17) Uani 1 1 d .
H909 H 0.895(4) 0.712(4) -0.025(3) 0.043(8) Uiso 1 1 d .
H4A H 0.424(4) 0.178(4) 0.307(3) 0.038(8) Uiso 1 1 d .
H4B H 0.390(5) 0.284(6) 0.170(5) 0.079(13) Uiso 1 1 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'
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_3
C4 O1 C3 116.1(2) .
C10 O4 C11 119.3(4) .
C6 N3 N2 114.8(3) .
C5 C1 C2 106.9(2) .
C5 C1 C10 111.3(3) .
C2 C1 C10 107.8(3) .
C5 C1 C12 112.1(3) .
C2 C1 C12 111.6(3) .
C10 C1 C12 107.1(3) .
C13 O3 C14 116.1(4) .
C6 C5 C4 104.1(3) .
C6 C5 C1 133.5(3) .
C4 C5 C1 122.4(3) .
C3 C2 C8 118.0(3) .
C3 C2 C1 125.4(2) .
C8 C2 C1 116.5(3) .
C4 N2 N3 101.9(3) .
C13 C12 C1 112.2(3) .
N6 C8 C2 178.1(4) .
N3 C6 C5 105.2(3) .
N3 C6 C7 122.0(3) .
C5 C6 C7 132.7(3) .
N4 C3 O1 109.5(3) .
N4 C3 C2 127.7(3) .
O1 C3 C2 122.8(3) .
O5 C10 O4 121.1(4) .
O5 C10 C1 125.6(4) .
O4 C10 C1 113.2(3) .
N2 C4 O1 120.3(3) .
N2 C4 C5 114.0(3) .
O1 C4 C5 125.7(2) .
O2 C13 O3 123.6(5) .
O2 C13 C12 123.8(5) .
O3 C13 C12 112.5(3) .
C95 C96 C92 66.4(17) .
C95 C92 C96 46.0(13) .
C95 C94 C95 180(4) 2_655
C94 C95 C96 154(4) .
C94 C95 C92 87(3) .
C96 C95 C92 67.6(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.355(4) .
O1 C3 1.362(3) .
O4 C10 1.297(5) .
O4 C11 1.425(6) .
N3 C6 1.348(4) .
N3 N2 1.351(4) .
C1 C5 1.499(4) .
C1 C2 1.518(5) .
C1 C10 1.523(5) .
C1 C12 1.545(5) .
O3 C13 1.312(5) .
O3 C14 1.431(7) .
N4 C3 1.323(5) .
C5 C6 1.376(4) .
C5 C4 1.398(5) .
C2 C3 1.376(5) .
C2 C8 1.408(4) .
C7 C6 1.483(6) .
N2 C4 1.317(4) .
C12 C13 1.470(6) .
C8 N6 1.150(4) .
C10 O5 1.175(5) .
O2 C13 1.191(5) .
C96 C95 1.41(2) .
C96 C92 1.81(4) .
C92 C95 1.79(5) .
C94 C95 1.08(2) .
C94 C95 1.08(2) 2_655
