#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:02:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180409 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/78/7207893.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_7207893
loop_
_publ_author_name
'Li, Jian'
'Liu, Yuejin'
'Li, Chunju'
'Jie, Haohua'
'Jia, Xueshun'
_publ_section_title
;
 Atom-economical synthesis of the functionalized spirocyclic
 oxindole-butenolide via three-component [2 + 2 + 1] cycloaddition
 strategy
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              1314
_journal_paper_doi               10.1039/c2gc00015f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.714(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.394(3)
_cell_length_b                   9.114(2)
_cell_length_c                   16.558(4)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.28
_cell_volume                     1371.2(6)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6888
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0369
_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)+(0.0415P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                1889
_reflns_number_total             2429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2gc00015f.txt
_cod_data_source_block           110527b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1371.3(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7207893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
C1 C 1.07670(17) 0.67222(17) 0.29642(10) 0.0401(4) Uani 1 1 d .
C2 C 1.20148(18) 0.6695(2) 0.36149(11) 0.0488(4) Uani 1 1 d .
H2 H 1.2815 0.6105 0.3599 0.059 Uiso 1 1 calc R
C3 C 1.20264(19) 0.7587(2) 0.42949(11) 0.0548(5) Uani 1 1 d .
H3 H 1.2854 0.7596 0.4745 0.066 Uiso 1 1 calc R
C4 C 1.0847(2) 0.8457(2) 0.43209(11) 0.0562(5) Uani 1 1 d .
H4 H 1.0887 0.9045 0.4785 0.067 Uiso 1 1 calc R
C5 C 0.95926(19) 0.84692(19) 0.36605(10) 0.0487(4) Uani 1 1 d .
H5 H 0.8790 0.9055 0.3677 0.058 Uiso 1 1 calc R
C6 C 0.95692(16) 0.75923(17) 0.29829(9) 0.0396(4) Uani 1 1 d .
C7 C 0.83876(16) 0.73194(17) 0.21967(9) 0.0401(4) Uani 1 1 d .
C8 C 0.91161(18) 0.61610(18) 0.17419(10) 0.0442(4) Uani 1 1 d .
C9 C 0.58726(18) 0.7440(2) 0.19886(11) 0.0483(4) Uani 1 1 d .
C10 C 0.63301(18) 0.86381(19) 0.15255(10) 0.0463(4) Uani 1 1 d .
H10 H 0.5705 0.9322 0.1198 0.056 Uiso 1 1 calc R
C11 C 0.77701(16) 0.85954(17) 0.16454(9) 0.0383(4) Uani 1 1 d .
C12 C 0.87305(18) 0.95462(18) 0.12907(10) 0.0429(4) Uani 1 1 d .
C13 C 0.8815(2) 1.1675(2) 0.04854(13) 0.0697(6) Uani 1 1 d .
H13A H 0.9573 1.1182 0.0284 0.084 Uiso 1 1 calc R
H13B H 0.9287 1.2369 0.0914 0.084 Uiso 1 1 calc R
C14 C 0.7807(3) 1.2450(3) -0.02042(14) 0.0843(7) Uani 1 1 d .
H14A H 0.7408 1.1771 -0.0647 0.126 Uiso 1 1 calc R
H14B H 0.8332 1.3210 -0.0408 0.126 Uiso 1 1 calc R
H14C H 0.7021 1.2877 -0.0009 0.126 Uiso 1 1 calc R
C15 C 1.15337(19) 0.4925(2) 0.19884(12) 0.0567(5) Uani 1 1 d .
H15A H 1.1127 0.4557 0.1435 0.085 Uiso 1 1 calc R
H15B H 1.1745 0.4120 0.2374 0.085 Uiso 1 1 calc R
H15C H 1.2425 0.5452 0.2004 0.085 Uiso 1 1 calc R
N1 N 1.04804(14) 0.59043(15) 0.22194(8) 0.0440(4) Uani 1 1 d .
O1 O 0.71011(11) 0.66639(13) 0.23727(7) 0.0488(3) Uani 1 1 d .
O2 O 0.46899(13) 0.71005(16) 0.20681(9) 0.0709(4) Uani 1 1 d .
O3 O 0.85219(14) 0.55966(14) 0.10783(8) 0.0620(4) Uani 1 1 d .
O4 O 0.79817(12) 1.06072(13) 0.08298(7) 0.0526(3) Uani 1 1 d .
O5 O 1.00250(13) 0.93314(15) 0.14056(8) 0.0634(4) Uani 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
C2 C1 C6 121.91(16)
C2 C1 N1 127.73(15)
C6 C1 N1 110.34(13)
C1 C2 C3 117.05(16)
C1 C2 H2 121.5
C3 C2 H2 121.5
C4 C3 C2 121.62(16)
C4 C3 H3 119.2
C2 C3 H3 119.2
C3 C4 C5 120.68(17)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 118.22(16)
C6 C5 H5 120.9
C4 C5 H5 120.9
C5 C6 C1 120.50(15)
C5 C6 C7 131.28(15)
C1 C6 C7 108.18(13)
O1 C7 C11 103.26(12)
O1 C7 C6 111.48(12)
C11 C7 C6 119.03(13)
O1 C7 C8 108.14(13)
C11 C7 C8 112.44(13)
C6 C7 C8 102.31(12)
O3 C8 N1 127.54(16)
O3 C8 C7 124.70(15)
N1 C8 C7 107.75(14)
O2 C9 O1 121.02(16)
O2 C9 C10 131.20(17)
O1 C9 C10 107.78(14)
C11 C10 C9 109.07(15)
C11 C10 H10 125.5
C9 C10 H10 125.5
C10 C11 C12 129.12(15)
C10 C11 C7 109.76(14)
C12 C11 C7 121.05(13)
O5 C12 O4 125.60(16)
O5 C12 C11 122.63(15)
O4 C12 C11 111.75(14)
O4 C13 C14 108.83(17)
O4 C13 H13A 109.9
C14 C13 H13A 109.9
O4 C13 H13B 109.9
C14 C13 H13B 109.9
H13A C13 H13B 108.3
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N1 C15 H15A 109.5
N1 C15 H15B 109.5
H15A C15 H15B 109.5
N1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 N1 C1 111.39(13)
C8 N1 C15 124.26(14)
C1 N1 C15 124.35(13)
C9 O1 C7 110.11(12)
C12 O4 C13 117.18(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.376(2)
C1 C6 1.383(2)
C1 N1 1.407(2)
C2 C3 1.387(2)
C2 H2 0.9300
C3 C4 1.372(2)
C3 H3 0.9300
C4 C5 1.389(2)
C4 H4 0.9300
C5 C6 1.373(2)
C5 H5 0.9300
C6 C7 1.502(2)
C7 O1 1.4428(18)
C7 C11 1.501(2)
C7 C8 1.553(2)
C8 O3 1.2133(19)
C8 N1 1.345(2)
C9 O2 1.1923(19)
C9 O1 1.365(2)
C9 C10 1.460(2)
C10 C11 1.317(2)
C10 H10 0.9300
C11 C12 1.476(2)
C12 O5 1.1983(19)
C12 O4 1.3190(19)
C13 O4 1.453(2)
C13 C14 1.466(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 N1 1.454(2)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
C6 C1 C2 C3 -0.2(2)
N1 C1 C2 C3 -178.74(16)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 0.1(3)
C3 C4 C5 C6 -0.2(3)
C4 C5 C6 C1 0.1(3)
C4 C5 C6 C7 177.65(16)
C2 C1 C6 C5 0.1(2)
N1 C1 C6 C5 178.87(14)
C2 C1 C6 C7 -177.94(15)
N1 C1 C6 C7 0.79(18)
C5 C6 C7 O1 -62.3(2)
C1 C6 C7 O1 115.52(14)
C5 C6 C7 C11 57.7(2)
C1 C6 C7 C11 -124.46(15)
C5 C6 C7 C8 -177.65(17)
C1 C6 C7 C8 0.15(16)
O1 C7 C8 O3 60.4(2)
C11 C7 C8 O3 -53.0(2)
C6 C7 C8 O3 178.14(16)
O1 C7 C8 N1 -118.84(14)
C11 C7 C8 N1 127.80(14)
C6 C7 C8 N1 -1.07(16)
O2 C9 C10 C11 178.1(2)
O1 C9 C10 C11 -1.39(19)
C9 C10 C11 C12 178.05(15)
C9 C10 C11 C7 1.08(19)
O1 C7 C11 C10 -0.40(17)
C6 C7 C11 C10 -124.54(16)
C8 C7 C11 C10 115.92(15)
O1 C7 C11 C12 -177.66(13)
C6 C7 C11 C12 58.2(2)
C8 C7 C11 C12 -61.34(18)
C10 C11 C12 O5 -174.81(18)
C7 C11 C12 O5 1.9(2)
C10 C11 C12 O4 3.7(2)
C7 C11 C12 O4 -179.59(14)
O3 C8 N1 C1 -177.56(17)
C7 C8 N1 C1 1.62(18)
O3 C8 N1 C15 3.4(3)
C7 C8 N1 C15 -177.39(15)
C2 C1 N1 C8 177.06(16)
C6 C1 N1 C8 -1.58(19)
C2 C1 N1 C15 -3.9(3)
C6 C1 N1 C15 177.43(15)
O2 C9 O1 C7 -178.39(16)
C10 C9 O1 C7 1.12(18)
C11 C7 O1 C9 -0.48(16)
C6 C7 O1 C9 128.46(14)
C8 C7 O1 C9 -119.81(14)
O5 C12 O4 C13 -5.2(3)
C11 C12 O4 C13 176.35(15)
C14 C13 O4 C12 161.92(17)
