#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117815.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_7117815
loop_
_publ_author_name
'Rong Zhou'
'Kai Zhang'
'Yusong Chen'
'Qiang Meng'
'Yiyi Liu'
'Ruifeng Li'
'Zhengjie He'
_publ_section_title
;
 P(NMe2)3-mediated reductive [1+4] annulation of isatins with enones: a
 facile synthesis of spirooxindole-dihydrofurans
;
_journal_name_full               Chem.Commun.
_journal_page_first              14663
_journal_paper_doi               10.1039/C5cc03676C
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C27 H19 N3 O3'
_chemical_formula_weight         433.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-02 deposited with the CCDC.
2015-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.112(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.917(6)
_cell_length_b                   9.529(2)
_cell_length_c                   23.123(8)
_cell_measurement_temperature    296(2)
_cell_volume                     4373(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22685
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       0.0016(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   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0382
_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)+(0.0264P)²+2.9401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                2859
_reflns_number_total             3880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03676c2.cif
_cod_data_source_block           zrr3
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7117815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.44875(7) 0.47961(14) 0.07253(7) 0.0541(4) Uani 1 1 d . . .
N2 N 0.33049(8) 0.06556(15) 0.05750(7) 0.0614(4) Uani 1 1 d . . .
N3 N 0.64576(9) 0.1984(2) 0.10174(9) 0.0868(6) Uani 1 1 d . . .
O1 O 0.51575(7) 0.43808(13) 0.17827(6) 0.0697(4) Uani 1 1 d . . .
O2 O 0.48479(6) 0.08421(12) 0.18107(5) 0.0558(3) Uani 1 1 d . . .
O3 O 0.42182(7) -0.06043(13) 0.06220(7) 0.0767(4) Uani 1 1 d . . .
C1 C 0.43100(8) 0.40560(17) 0.01536(8) 0.0496(4) Uani 1 1 d . . .
C2 C 0.44996(8) 0.26556(17) 0.02811(8) 0.0474(4) Uani 1 1 d . . .
C3 C 0.44057(9) 0.1755(2) -0.02136(8) 0.0592(5) Uani 1 1 d . . .
H3 H 0.4531 0.0817 -0.0134 0.071 Uiso 1 1 calc R . .
C4 C 0.41226(10) 0.2268(2) -0.08316(9) 0.0708(6) Uani 1 1 d . . .
H4 H 0.4059 0.1669 -0.1170 0.085 Uiso 1 1 calc R . .
C5 C 0.39346(10) 0.3645(3) -0.09508(10) 0.0740(6) Uani 1 1 d . . .
H5 H 0.3744 0.3965 -0.1370 0.089 Uiso 1 1 calc R . .
C6 C 0.40211(9) 0.4573(2) -0.04628(10) 0.0651(5) Uani 1 1 d . . .
H6 H 0.3890 0.5507 -0.0546 0.078 Uiso 1 1 calc R . .
C7 C 0.48072(8) 0.24494(16) 0.09966(8) 0.0468(4) Uani 1 1 d . . .
C8 C 0.48553(8) 0.39834(18) 0.12370(9) 0.0522(4) Uani 1 1 d . . .
C9 C 0.43561(10) 0.62790(18) 0.07653(11) 0.0771(6) Uani 1 1 d . . .
H9A H 0.4565 0.6574 0.1204 0.116 Uiso 1 1 calc R . .
H9B H 0.3879 0.6432 0.0597 0.116 Uiso 1 1 calc R . .
H9C H 0.4537 0.6811 0.0522 0.116 Uiso 1 1 calc R . .
C10 C 0.54684(8) 0.16711(17) 0.13204(8) 0.0505(4) Uani 1 1 d . . .
C11 C 0.54522(8) 0.08310(17) 0.17770(8) 0.0510(4) Uani 1 1 d . . .
C12 C 0.43656(8) 0.15480(16) 0.12497(7) 0.0472(4) Uani 1 1 d . . .
C13 C 0.39702(10) 0.03839(17) 0.07734(8) 0.0556(4) Uani 1 1 d . . .
C14 C 0.38229(8) 0.22824(16) 0.13641(8) 0.0479(4) Uani 1 1 d . . .
C15 C 0.32067(9) 0.17543(18) 0.09353(8) 0.0557(4) Uani 1 1 d . . .
C16 C 0.26105(10) 0.2255(2) 0.09141(11) 0.0773(6) Uani 1 1 d . . .
H16 H 0.2198 0.1914 0.0618 0.093 Uiso 1 1 calc R . .
C17 C 0.26438(11) 0.3286(2) 0.13480(12) 0.0855(7) Uani 1 1 d . . .
H17 H 0.2246 0.3653 0.1338 0.103 Uiso 1 1 calc R . .
C18 C 0.32483(11) 0.3778(2) 0.17907(11) 0.0755(6) Uani 1 1 d . . .
H18 H 0.3257 0.4450 0.2086 0.091 Uiso 1 1 calc R . .
C19 C 0.38489(9) 0.32819(19) 0.18034(9) 0.0600(5) Uani 1 1 d . . .
H19 H 0.4260 0.3618 0.2102 0.072 Uiso 1 1 calc R . .
C20 C 0.27787(11) -0.0296(2) 0.01639(11) 0.0931(7) Uani 1 1 d . . .
H20A H 0.2960 -0.0913 -0.0053 0.140 Uiso 1 1 calc R . .
H20B H 0.2415 0.0237 -0.0145 0.140 Uiso 1 1 calc R . .
H20C H 0.2615 -0.0840 0.0418 0.140 Uiso 1 1 calc R . .
C21 C 0.60209(9) 0.18404(19) 0.11610(9) 0.0597(5) Uani 1 1 d . . .
C22 C 0.59535(9) -0.01358(18) 0.22212(8) 0.0553(4) Uani 1 1 d . . .
C23 C 0.66293(10) 0.0181(2) 0.25011(10) 0.0782(6) Uani 1 1 d . . .
H23 H 0.6781 0.1038 0.2421 0.094 Uiso 1 1 calc R . .
C24 C 0.70841(12) -0.0790(3) 0.29048(12) 0.0978(8) Uani 1 1 d . . .
H24 H 0.7542 -0.0578 0.3098 0.117 Uiso 1 1 calc R . .
C25 C 0.68607(14) -0.2056(3) 0.30191(12) 0.0990(8) Uani 1 1 d . . .
H25 H 0.7168 -0.2701 0.3290 0.119 Uiso 1 1 calc R . .
C26 C 0.61914(13) -0.2381(3) 0.27396(12) 0.0918(7) Uani 1 1 d . . .
H26 H 0.6043 -0.3245 0.2817 0.110 Uiso 1 1 calc R . .
C27 C 0.57370(10) -0.1423(2) 0.23432(9) 0.0691(5) Uani 1 1 d . . .
H27 H 0.5280 -0.1641 0.2155 0.083 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 N1 C1 111.11(14) . .
C8 N1 C9 124.07(17) . .
C1 N1 C9 124.54(16) . .
C13 N2 C15 110.73(14) . .
C13 N2 C20 122.79(17) . .
C15 N2 C20 124.77(17) . .
C11 O2 C12 108.14(12) . .
C6 C1 C2 121.68(17) . .
C6 C1 N1 128.08(16) . .
C2 C1 N1 110.17(14) . .
C3 C2 C1 119.78(16) . .
C3 C2 C7 132.07(15) . .
C1 C2 C7 108.12(14) . .
C2 C3 C4 118.88(18) . .
C2 C3 H3 120.6 . .
C4 C3 H3 120.6 . .
C5 C4 C3 120.8(2) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 121.60(19) . .
C4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C5 C6 C1 117.30(18) . .
C5 C6 H6 121.4 . .
C1 C6 H6 121.4 . .
C2 C7 C10 119.61(14) . .
C2 C7 C8 101.57(13) . .
C10 C7 C8 112.30(13) . .
C2 C7 C12 114.66(13) . .
C10 C7 C12 99.14(12) . .
C8 C7 C12 109.80(13) . .
O1 C8 N1 126.19(16) . .
O1 C8 C7 126.31(16) . .
N1 C8 C7 107.50(14) . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C21 125.83(15) . .
C11 C10 C7 110.08(15) . .
C21 C10 C7 124.08(15) . .
C10 C11 O2 113.17(14) . .
C10 C11 C22 131.72(17) . .
O2 C11 C22 115.04(15) . .
O2 C12 C14 113.09(13) . .
O2 C12 C13 106.33(12) . .
C14 C12 C13 102.37(14) . .
O2 C12 C7 104.82(12) . .
C14 C12 C7 117.95(13) . .
C13 C12 C7 111.90(13) . .
O3 C13 N2 126.97(17) . .
O3 C13 C12 125.44(17) . .
N2 C13 C12 107.57(15) . .
C19 C14 C15 120.12(16) . .
C19 C14 C12 131.82(15) . .
C15 C14 C12 108.04(15) . .
C16 C15 C14 121.52(18) . .
C16 C15 N2 128.23(17) . .
C14 C15 N2 110.20(15) . .
C15 C16 C17 117.68(19) . .
C15 C16 H16 121.2 . .
C17 C16 H16 121.2 . .
C18 C17 C16 121.5(2) . .
C18 C17 H17 119.3 . .
C16 C17 H17 119.3 . .
C17 C18 C19 120.5(2) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C14 C19 C18 118.58(18) . .
C14 C19 H19 120.7 . .
C18 C19 H19 120.7 . .
N2 C20 H20A 109.5 . .
N2 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
N2 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N3 C21 C10 178.4(2) . .
C23 C22 C27 119.44(17) . .
C23 C22 C11 121.94(17) . .
C27 C22 C11 118.59(17) . .
C22 C23 C24 119.5(2) . .
C22 C23 H23 120.2 . .
C24 C23 H23 120.2 . .
C25 C24 C23 120.2(2) . .
C25 C24 H24 119.9 . .
C23 C24 H24 119.9 . .
C26 C25 C24 120.6(2) . .
C26 C25 H25 119.7 . .
C24 C25 H25 119.7 . .
C25 C26 C27 119.6(2) . .
C25 C26 H26 120.2 . .
C27 C26 H26 120.2 . .
C26 C27 C22 120.6(2) . .
C26 C27 H27 119.7 . .
C22 C27 H27 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C8 1.356(2) .
N1 C1 1.400(2) .
N1 C9 1.453(2) .
N2 C13 1.355(2) .
N2 C15 1.410(2) .
N2 C20 1.458(2) .
N3 C21 1.147(2) .
O1 C8 1.210(2) .
O2 C11 1.3593(19) .
O2 C12 1.4452(18) .
O3 C13 1.211(2) .
C1 C6 1.382(2) .
C1 C2 1.392(2) .
C2 C3 1.374(2) .
C2 C7 1.511(2) .
C3 C4 1.383(3) .
C3 H3 0.9300 .
C4 C5 1.368(3) .
C4 H4 0.9300 .
C5 C6 1.382(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C10 1.513(2) .
C7 C8 1.551(2) .
C7 C12 1.580(2) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.337(2) .
C10 C21 1.417(3) .
C11 C22 1.467(2) .
C12 C14 1.497(2) .
C12 C13 1.544(2) .
C14 C19 1.376(2) .
C14 C15 1.387(2) .
C15 C16 1.372(3) .
C16 C17 1.384(3) .
C16 H16 0.9300 .
C17 C18 1.368(3) .
C17 H17 0.9300 .
C18 C19 1.387(3) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C22 C23 1.375(3) .
C22 C27 1.387(3) .
C23 C24 1.389(3) .
C23 H23 0.9300 .
C24 C25 1.370(3) .
C24 H24 0.9300 .
C25 C26 1.364(3) .
C25 H25 0.9300 .
C26 C27 1.375(3) .
C26 H26 0.9300 .
C27 H27 0.9300 .
