#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/53/2235301.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235301
loop_
_publ_author_name
'Al Mamari, Khalil'
'Ennajih, Hamid'
'Bouhfid, Rachid'
'Essassi, El Mokhtar'
'Ng, Seik Weng'
_publ_section_title
;
 1,1''-Bis(prop-2-en-1-yl)-1,1'',2,2''-tetrahydrodispiro[indole-3,7'-[6,9]diazatricyclo[7.3.0.0^2,6^]dodecane-8',3''-indole]-2,2''-dione
;
_journal_coeditor_code           XU5527
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1637
_journal_paper_doi               10.1107/S1600536812019216
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C30 H32 N4 O2'
_chemical_formula_moiety         'C30 H32 N4 O2'
_chemical_formula_sum            'C30 H32 N4 O2'
_chemical_formula_weight         480.60
_chemical_name_systematic
;
1,1''-Bis(prop-2-en-1-yl)-1,1'',2,2''-tetrahydrodispiro[indole-3,7'-
[6,9]diazatricyclo[7.3.0.0^2,6^]dodecane-8',3''-indole]-2,2''-dione
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 111.1190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.9484(2)
_cell_length_b                   9.91730(10)
_cell_length_c                   17.5713(3)
_cell_measurement_reflns_used    8483
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.66
_cell_measurement_theta_min      2.49
_cell_volume                     2429.95(6)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       '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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13297
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0678P)²+1.2982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                2441
_reflns_number_total             2797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5527.cif
_cod_data_source_block           I
_cod_original_cell_volume        2429.94(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235301
_cod_database_fobs_code          2235301
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.43126(6) 0.47958(9) 0.37259(6) 0.0390(2) Uani d . 1 1
N N1 0.52761(7) 0.66607(10) 0.39788(6) 0.0315(2) Uani d . 1 1
N N2 0.59105(6) 0.39146(9) 0.30977(6) 0.0285(2) Uani d . 1 1
C C1 0.49026(7) 0.54901(11) 0.35787(6) 0.0283(2) Uani d . 1 1
C C2 0.53923(7) 0.51947(10) 0.29458(6) 0.0255(2) Uani d . 1 1
C C3 0.61013(7) 0.63591(11) 0.31150(7) 0.0272(2) Uani d . 1 1
C C4 0.68373(8) 0.66113(12) 0.28314(8) 0.0348(3) Uani d . 1 1
H H4 0.6923 0.6064 0.2433 0.042 Uiso calc R 1 1
C C5 0.74493(8) 0.76994(13) 0.31530(9) 0.0406(3) Uani d . 1 1
H H5 0.7937 0.7891 0.2958 0.049 Uiso calc R 1 1
C C6 0.73379(9) 0.84936(13) 0.37577(9) 0.0409(3) Uani d . 1 1
H H6 0.7752 0.9215 0.3964 0.049 Uiso calc R 1 1
C C7 0.66169(9) 0.82346(12) 0.40655(8) 0.0373(3) Uani d . 1 1
H H7 0.6546 0.8762 0.4478 0.045 Uiso calc R 1 1
C C8 0.60104(8) 0.71628(11) 0.37335(7) 0.0289(2) Uani d . 1 1
C C9 0.50268(10) 0.72080(14) 0.46422(8) 0.0419(3) Uani d . 1 1
H H9A 0.5611 0.7350 0.5110 0.050 Uiso calc R 1 1
H H9B 0.4644 0.6548 0.4797 0.050 Uiso calc R 1 1
C C10 0.44850(11) 0.85017(16) 0.44444(10) 0.0520(4) Uani d . 1 1
H H10 0.4341 0.8903 0.4865 0.062 Uiso calc R 1 1
C C11 0.41912(12) 0.91320(17) 0.37480(12) 0.0618(4) Uani d . 1 1
H H11A 0.4316 0.8775 0.3307 0.074 Uiso calc R 1 1
H H11B 0.3857 0.9939 0.3691 0.074 Uiso calc R 1 1
C C12 0.66448(9) 0.37194(13) 0.39119(7) 0.0376(3) Uani d . 1 1
H H12A 0.6392 0.3916 0.4337 0.045 Uiso calc R 1 1
H H12B 0.7200 0.4284 0.3989 0.045 Uiso calc R 1 1
C C13 0.68964(10) 0.22205(14) 0.39088(9) 0.0486(4) Uani d . 1 1
H H13A 0.7495 0.2111 0.3819 0.058 Uiso calc R 1 1
H H13B 0.6959 0.1804 0.4425 0.058 Uiso calc R 1 1
C C14 0.60698(9) 0.15842(13) 0.32126(9) 0.0424(3) Uani d . 1 1
H H14A 0.6275 0.1318 0.2770 0.051 Uiso calc R 1 1
H H14B 0.5822 0.0799 0.3401 0.051 Uiso calc R 1 1
C C15 0.53166(8) 0.26936(11) 0.29411(7) 0.0315(3) Uani d . 1 1
H H15 0.4925 0.2690 0.3284 0.038 Uiso calc R 1 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 C8 . . 111.22(9)
C1 N1 C9 . . 123.71(10)
C8 N1 C9 . . 124.63(10)
C2 N2 C15 . . 115.95(8)
C2 N2 C12 . . 116.96(9)
C15 N2 C12 . . 105.26(9)
O1 C1 N1 . . 124.30(10)
O1 C1 C2 . . 127.27(10)
N1 C1 C2 . . 108.39(9)
N2 C2 C3 . . 109.72(8)
N2 C2 C1 . . 112.72(8)
C3 C2 C1 . . 100.98(8)
N2 C2 C2 . 2_655 109.62(6)
C3 C2 C2 . 2_655 114.12(7)
C1 C2 C2 . 2_655 109.52(9)
C4 C3 C8 . . 119.41(10)
C4 C3 C2 . . 130.87(10)
C8 C3 C2 . . 109.23(9)
C3 C4 C5 . . 118.94(11)
C3 C4 H4 . . 120.5
C5 C4 H4 . . 120.5
C6 C5 C4 . . 120.64(11)
C6 C5 H5 . . 119.7
C4 C5 H5 . . 119.7
C5 C6 C7 . . 121.24(11)
C5 C6 H6 . . 119.4
C7 C6 H6 . . 119.4
C8 C7 C6 . . 117.35(12)
C8 C7 H7 . . 121.3
C6 C7 H7 . . 121.3
C7 C8 C3 . . 122.38(11)
C7 C8 N1 . . 127.46(11)
C3 C8 N1 . . 110.04(9)
N1 C9 C10 . . 114.21(11)
N1 C9 H9A . . 108.7
C10 C9 H9A . . 108.7
N1 C9 H9B . . 108.7
C10 C9 H9B . . 108.7
H9A C9 H9B . . 107.6
C11 C10 C9 . . 127.15(14)
C11 C10 H10 . . 116.4
C9 C10 H10 . . 116.4
C10 C11 H11A . . 120.0
C10 C11 H11B . . 120.0
H11A C11 H11B . . 120.0
N2 C12 C13 . . 102.86(10)
N2 C12 H12A . . 111.2
C13 C12 H12A . . 111.2
N2 C12 H12B . . 111.2
C13 C12 H12B . . 111.2
H12A C12 H12B . . 109.1
C14 C13 C12 . . 105.93(10)
C14 C13 H13A . . 110.5
C12 C13 H13A . . 110.5
C14 C13 H13B . . 110.5
C12 C13 H13B . . 110.5
H13A C13 H13B . . 108.7
C15 C14 C13 . . 104.24(10)
C15 C14 H14A . . 110.9
C13 C14 H14A . . 110.9
C15 C14 H14B . . 110.9
C13 C14 H14B . . 110.9
H14A C14 H14B . . 108.9
N2 C15 C15 . 2_655 107.95(8)
N2 C15 C14 . . 102.03(9)
C15 C15 C14 2_655 . 116.41(10)
N2 C15 H15 . . 110.0
C15 C15 H15 2_655 . 110.0
C14 C15 H15 . . 110.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2178(13)
N1 C1 . 1.3677(15)
N1 C8 . 1.4070(14)
N1 C9 . 1.4511(15)
N2 C2 . 1.4608(13)
N2 C15 . 1.4677(14)
N2 C12 . 1.4688(14)
C1 C2 . 1.5637(14)
C2 C3 . 1.5226(14)
C2 C2 2_655 1.583(2)
C3 C4 . 1.3843(15)
C3 C8 . 1.3933(16)
C4 C5 . 1.3958(17)
C4 H4 . 0.9300
C5 C6 . 1.380(2)
C5 H5 . 0.9300
C6 C7 . 1.3929(18)
C6 H6 . 0.9300
C7 C8 . 1.3824(16)
C7 H7 . 0.9300
C9 C10 . 1.490(2)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.301(3)
C10 H10 . 0.9300
C11 H11A . 0.9300
C11 H11B . 0.9300
C12 C13 . 1.5339(18)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 C14 . 1.5273(19)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 C15 . 1.5226(16)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C15 2_655 1.497(2)
C15 H15 . 0.9800
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C8 N1 C1 O1 . . 173.93(11)
C9 N1 C1 O1 . . 1.24(18)
C8 N1 C1 C2 . . -3.80(12)
C9 N1 C1 C2 . . -176.49(10)
C15 N2 C2 C3 . . -178.61(9)
C12 N2 C2 C3 . . 56.22(12)
C15 N2 C2 C1 . . 69.71(11)
C12 N2 C2 C1 . . -55.46(12)
C15 N2 C2 C2 . 2_655 -52.56(13)
C12 N2 C2 C2 . 2_655 -177.72(10)
O1 C1 C2 N2 . . -58.18(14)
N1 C1 C2 N2 . . 119.46(10)
O1 C1 C2 C3 . . -175.17(11)
N1 C1 C2 C3 . . 2.47(11)
O1 C1 C2 C2 . 2_655 64.14(12)
N1 C1 C2 C2 . 2_655 -118.22(7)
N2 C2 C3 C4 . . 52.23(15)
C1 C2 C3 C4 . . 171.40(11)
C2 C2 C3 C4 2_655 . -71.23(15)
N2 C2 C3 C8 . . -119.51(10)
C1 C2 C3 C8 . . -0.34(11)
C2 C2 C3 C8 2_655 . 117.03(11)
C8 C3 C4 C5 . . -2.36(17)
C2 C3 C4 C5 . . -173.40(11)
C3 C4 C5 C6 . . 1.51(19)
C4 C5 C6 C7 . . 0.1(2)
C5 C6 C7 C8 . . -0.85(19)
C6 C7 C8 C3 . . -0.04(18)
C6 C7 C8 N1 . . 175.65(11)
C4 C3 C8 C7 . . 1.66(17)
C2 C3 C8 C7 . . 174.50(10)
C4 C3 C8 N1 . . -174.70(10)
C2 C3 C8 N1 . . -1.86(12)
C1 N1 C8 C7 . . -172.47(11)
C9 N1 C8 C7 . . 0.14(19)
C1 N1 C8 C3 . . 3.66(13)
C9 N1 C8 C3 . . 176.27(11)
C1 N1 C9 C10 . . -113.01(14)
C8 N1 C9 C10 . . 75.28(15)
N1 C9 C10 C11 . . 3.0(2)
C2 N2 C12 C13 . . 169.82(10)
C15 N2 C12 C13 . . 39.45(12)
N2 C12 C13 C14 . . -17.94(15)
C12 C13 C14 C15 . . -8.73(15)
C2 N2 C15 C15 . 2_655 60.60(14)
C12 N2 C15 C15 . 2_655 -168.44(11)
C2 N2 C15 C14 . . -176.24(10)
C12 N2 C15 C14 . . -45.28(12)
C13 C14 C15 N2 . . 32.17(13)
C13 C14 C15 C15 . 2_655 149.40(12)
