#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:09:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180170 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/66/7106637.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_7106637
loop_
_publ_author_name
'Laurent El Kaim'
'Laurence Grimaud'
'Xavier-Frederic Le Goff'
'Luis D. Miranda'
'Martha Menes-Arzate'
_publ_section_title
;
 Straightforward four-component access to spiroindolines.
;
_journal_name_full               'Chem. Commun.'
_journal_page_first              8145
_journal_paper_doi               10.1039/c1cc12236c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C26 H28 N4 O4'
_chemical_formula_sum            'C26 H28 N4 O4'
_chemical_formula_weight         460.52
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   13.237(1)
_cell_length_b                   14.763(1)
_cell_length_c                   24.055(1)
_cell_measurement_reflns_used    5841
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     4700.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.0(1)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33090
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0555
_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)+(0.0619P)²+2.7883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                4184
_reflns_number_total             5373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12236c.txt
_cod_data_source_block           mm77
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7106637
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28507(9) 0.35351(9) 0.24540(5) 0.0380(3) Uani 1 1 d . . .
O2 O 0.12787(12) 0.08857(9) 0.19123(6) 0.0496(4) Uani 1 1 d . . .
O3 O 0.47321(14) 0.41166(18) -0.01719(8) 0.0800(6) Uani 1 1 d . . .
O4 O 0.4166(3) 0.28273(16) -0.04139(10) 0.1329(13) Uani 1 1 d . . .
N1 N -0.00191(12) 0.51563(11) 0.22698(7) 0.0356(4) Uani 1 1 d . . .
H1N H -0.0467(16) 0.5387(14) 0.2516(9) 0.043 Uiso 1 1 d . . .
N2 N 0.12773(10) 0.41454(9) 0.25967(6) 0.0282(3) Uani 1 1 d . . .
N3 N 0.11327(11) 0.23927(9) 0.18507(6) 0.0321(3) Uani 1 1 d . . .
N4 N 0.41790(18) 0.34675(16) -0.01097(8) 0.0608(6) Uani 1 1 d . . .
C1 C 0.00659(12) 0.54386(12) 0.17242(8) 0.0319(4) Uani 1 1 d . . .
C2 C -0.01711(14) 0.62824(13) 0.15069(9) 0.0393(4) Uani 1 1 d . . .
H2 H -0.0446 0.6744 0.1737 0.047 Uiso 1 1 calc R . .
C3 C 0.00018(15) 0.64360(14) 0.09507(10) 0.0444(5) Uani 1 1 d . . .
H3 H -0.0151 0.7013 0.0798 0.053 Uiso 1 1 calc R . .
C4 C 0.03946(16) 0.57676(15) 0.06093(9) 0.0444(5) Uani 1 1 d . . .
H4 H 0.0520 0.5891 0.0228 0.053 Uiso 1 1 calc R . .
C5 C 0.06053(14) 0.49109(14) 0.08275(8) 0.0382(4) Uani 1 1 d . . .
H5 H 0.0857 0.4444 0.0594 0.046 Uiso 1 1 calc R . .
C6 C 0.04440(12) 0.47491(12) 0.13853(7) 0.0299(4) Uani 1 1 d . . .
C7 C 0.04798(12) 0.38797(11) 0.17206(7) 0.0281(4) Uani 1 1 d . . .
C8 C 0.02924(12) 0.42250(11) 0.23239(7) 0.0285(4) Uani 1 1 d . . .
H8 H -0.0232 0.3854 0.2518 0.034 Uiso 1 1 calc R . .
C9 C 0.19809(12) 0.36861(11) 0.23089(7) 0.0280(4) Uani 1 1 d . . .
C10 C 0.14921(12) 0.33374(11) 0.17610(7) 0.0269(3) Uani 1 1 d . . .
C11 C 0.00214(14) 0.23163(13) 0.18219(9) 0.0393(4) Uani 1 1 d . . .
H11A H -0.0276 0.2273 0.2199 0.047 Uiso 1 1 calc R . .
H11B H -0.0183 0.1778 0.1603 0.047 Uiso 1 1 calc R . .
C12 C -0.03033(14) 0.31783(12) 0.15369(9) 0.0370(4) Uani 1 1 d . . .
H12A H -0.0990 0.3358 0.1656 0.044 Uiso 1 1 calc R . .
H12B H -0.0298 0.3104 0.1128 0.044 Uiso 1 1 calc R . .
C13 C 0.13929(12) 0.44513(12) 0.31770(7) 0.0302(4) Uani 1 1 d . . .
H13 H 0.0754 0.4772 0.3279 0.036 Uiso 1 1 calc R . .
C14 C 0.22455(17) 0.51277(17) 0.32509(9) 0.0529(6) Uani 1 1 d . . .
H14A H 0.2128 0.5661 0.3010 0.064 Uiso 1 1 calc R . .
H14B H 0.2894 0.4847 0.3140 0.064 Uiso 1 1 calc R . .
C15 C 0.2299(2) 0.5428(2) 0.38602(11) 0.0713(9) Uani 1 1 d . . .
H15A H 0.2879 0.5844 0.3910 0.086 Uiso 1 1 calc R . .
H15B H 0.1675 0.5761 0.3958 0.086 Uiso 1 1 calc R . .
C16 C 0.24193(19) 0.4623(3) 0.42481(10) 0.0788(10) Uani 1 1 d . . .
H16A H 0.3072 0.4318 0.4173 0.095 Uiso 1 1 calc R . .
H16B H 0.2427 0.4837 0.4638 0.095 Uiso 1 1 calc R . .
C17 C 0.1571(2) 0.39592(19) 0.41704(9) 0.0630(7) Uani 1 1 d . . .
H17A H 0.0928 0.4246 0.4284 0.076 Uiso 1 1 calc R . .
H17B H 0.1685 0.3427 0.4413 0.076 Uiso 1 1 calc R . .
C18 C 0.14859(18) 0.36448(15) 0.35674(9) 0.0472(5) Uani 1 1 d . . .
H18A H 0.2091 0.3286 0.3467 0.057 Uiso 1 1 calc R . .
H18B H 0.0886 0.3250 0.3526 0.057 Uiso 1 1 calc R . .
C19 C 0.17005(15) 0.16314(12) 0.18792(8) 0.0373(4) Uani 1 1 d . . .
C20 C 0.28284(15) 0.16726(15) 0.18548(10) 0.0477(5) Uani 1 1 d . . .
H20A H 0.3114 0.1268 0.2137 0.071 Uiso 1 1 calc R . .
H20B H 0.3052 0.2295 0.1926 0.071 Uiso 1 1 calc R . .
H20C H 0.3058 0.1482 0.1486 0.071 Uiso 1 1 calc R . .
C21 C 0.21687(12) 0.34087(11) 0.12562(7) 0.0274(4) Uani 1 1 d . . .
C22 C 0.20495(16) 0.28092(13) 0.08117(8) 0.0398(4) Uani 1 1 d . . .
H22 H 0.1517 0.2378 0.0819 0.048 Uiso 1 1 calc R . .
C23 C 0.26957(19) 0.28361(14) 0.03631(8) 0.0479(5) Uani 1 1 d . . .
H23 H 0.2627 0.2415 0.0067 0.057 Uiso 1 1 calc R . .
C24 C 0.34417(16) 0.34840(14) 0.03518(8) 0.0404(5) Uani 1 1 d . . .
C25 C 0.35461(14) 0.41229(13) 0.07656(8) 0.0362(4) Uani 1 1 d . . .
H25 H 0.4044 0.4584 0.0739 0.043 Uiso 1 1 calc R . .
C26 C 0.29073(12) 0.40760(12) 0.12210(7) 0.0301(4) Uani 1 1 d . . .
H26 H 0.2975 0.4505 0.1513 0.036 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
_geom_angle_publ_flag
C1 N1 C8 110.51(15) . . ?
C1 N1 H1N 124.1(14) . . ?
C8 N1 H1N 119.2(14) . . ?
C9 N2 C8 115.25(14) . . ?
C9 N2 C13 124.75(14) . . ?
C8 N2 C13 119.46(13) . . ?
C19 N3 C11 119.47(15) . . ?
C19 N3 C10 127.40(14) . . ?
C11 N3 C10 112.51(13) . . ?
O4 N4 O3 123.8(2) . . ?
O4 N4 C24 117.6(2) . . ?
O3 N4 C24 118.5(2) . . ?
N1 C1 C2 127.63(18) . . ?
N1 C1 C6 111.33(16) . . ?
C2 C1 C6 121.03(18) . . ?
C3 C2 C1 118.48(19) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.43(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.42(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.80(17) . . ?
C5 C6 C7 131.22(16) . . ?
C1 C6 C7 108.51(16) . . ?
C6 C7 C12 113.45(14) . . ?
C6 C7 C8 102.33(13) . . ?
C12 C7 C8 112.48(15) . . ?
C6 C7 C10 119.54(14) . . ?
C12 C7 C10 104.59(13) . . ?
C8 C7 C10 104.24(13) . . ?
N1 C8 N2 111.82(14) . . ?
N1 C8 C7 105.87(14) . . ?
N2 C8 C7 104.45(13) . . ?
N1 C8 H8 111.5 . . ?
N2 C8 H8 111.5 . . ?
C7 C8 H8 111.5 . . ?
O1 C9 N2 126.65(16) . . ?
O1 C9 C10 124.94(15) . . ?
N2 C9 C10 108.37(13) . . ?
N3 C10 C21 111.75(13) . . ?
N3 C10 C9 108.66(14) . . ?
C21 C10 C9 114.26(13) . . ?
N3 C10 C7 102.39(12) . . ?
C21 C10 C7 114.95(14) . . ?
C9 C10 C7 103.86(13) . . ?
N3 C11 C12 103.93(14) . . ?
N3 C11 H11A 111.0 . . ?
C12 C11 H11A 111.0 . . ?
N3 C11 H11B 111.0 . . ?
C12 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
C11 C12 C7 104.29(14) . . ?
C11 C12 H12A 110.9 . . ?
C7 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C7 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
N2 C13 C14 112.93(14) . . ?
N2 C13 C18 110.67(15) . . ?
C14 C13 C18 112.48(17) . . ?
N2 C13 H13 106.8 . . ?
C14 C13 H13 106.8 . . ?
C18 C13 H13 106.8 . . ?
C13 C14 C15 109.69(17) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 111.5(2) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 110.84(19) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 111.8(2) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C13 C18 C17 110.76(19) . . ?
C13 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
O2 C19 N3 119.44(18) . . ?
O2 C19 C20 119.30(17) . . ?
N3 C19 C20 121.24(17) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.79(16) . . ?
C26 C21 C10 120.97(15) . . ?
C22 C21 C10 120.24(16) . . ?
C23 C22 C21 120.74(19) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 118.78(18) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 122.27(18) . . ?
C23 C24 N4 118.52(19) . . ?
C25 C24 N4 119.2(2) . . ?
C24 C25 C26 118.39(18) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 120.84(17) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
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
O1 C9 1.224(2) . ?
O2 C19 1.237(2) . ?
O3 N4 1.215(3) . ?
O4 N4 1.195(3) . ?
N1 C1 1.382(2) . ?
N1 C8 1.441(2) . ?
N1 H1N 0.90(2) . ?
N2 C9 1.344(2) . ?
N2 C8 1.464(2) . ?
N2 C13 1.475(2) . ?
N3 C19 1.354(2) . ?
N3 C11 1.477(2) . ?
N3 C10 1.489(2) . ?
N4 C24 1.478(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.397(2) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.517(2) . ?
C7 C12 1.530(2) . ?
C7 C8 1.558(2) . ?
C7 C10 1.564(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.556(2) . ?
C10 C21 1.512(2) . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(3) . ?
C13 C18 1.522(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.533(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.502(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.495(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.391(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.375(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(3) . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
