#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/35/2223550.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_2223550
loop_
_publ_author_name
'Benzeid, Hanane'
'Essassi, El Mokhtar'
'Saffon, Nathalie'
'Garrigues, Bernard'
'Ng, Seik Weng'
_publ_section_title
10-Allyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione
_journal_coeditor_code           SJ2637
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2322
_journal_paper_doi               10.1107/S1600536809034266
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H16 N2 O2'
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_name_systematic
;
\
10-Allyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,\
11(10H,11aH)-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.09880(10)
_cell_length_b                   11.7166(2)
_cell_length_c                   15.6592(3)
_cell_measurement_reflns_used    7433
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.17
_cell_volume                     1302.44(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20329
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         5.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0493
_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)+(0.086P)²+0.2922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                1900
_reflns_number_total             2263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2637.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_database_code               2223550
_cod_database_fobs_code          2223550
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'
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_disorder_assembly
_atom_site_disorder_group
O O1 0.3349(3) 0.89582(17) 0.62000(12) 0.0545(5) Uani d . 1 . .
O O2 -0.1387(3) 0.62142(13) 0.76109(11) 0.0423(4) Uani d . 1 . .
N N1 0.2785(2) 0.86934(15) 0.76059(12) 0.0312(4) Uani d . 1 . .
N N2 -0.0624(3) 0.77145(15) 0.67775(12) 0.0327(4) Uani d . 1 B .
C C1 0.2213(4) 0.88657(18) 0.67841(15) 0.0355(5) Uani d . 1 B .
C C2 -0.0695(3) 0.71719(17) 0.75353(14) 0.0301(4) Uani d . 1 . .
C C3 -0.0008(3) 0.78280(17) 0.82960(13) 0.0280(4) Uani d . 1 . .
C C4 0.1542(3) 0.85792(16) 0.83096(13) 0.0279(4) Uani d . 1 . .
C C5 0.1940(3) 0.91758(17) 0.90646(13) 0.0333(4) Uani d . 1 . .
H H5 0.2989 0.9678 0.9083 0.040 Uiso calc R 1 . .
C C6 0.0828(4) 0.9044(2) 0.97834(14) 0.0396(5) Uani d . 1 . .
H H6 0.1090 0.9476 1.0283 0.048 Uiso calc R 1 . .
C C7 -0.0675(4) 0.8278(2) 0.97772(14) 0.0407(5) Uani d . 1 . .
H H7 -0.1425 0.8172 1.0274 0.049 Uiso calc R 1 . .
C C8 -0.1059(3) 0.76768(19) 0.90409(14) 0.0359(5) Uani d . 1 . .
H H8 -0.2069 0.7144 0.9040 0.043 Uiso calc R 1 . .
C C9 -0.1524(4) 0.7262(2) 0.60032(14) 0.0399(5) Uani d D 1 . .
H H9A -0.2678 0.6823 0.6137 0.048 Uiso calc PR 0.50 A 1
H H9B -0.0651 0.6780 0.5667 0.048 Uiso calc PR 0.50 A 1
H H9C -0.2759 0.6916 0.6143 0.048 Uiso calc PR 0.50 A 2
H H9D -0.0719 0.6671 0.5736 0.048 Uiso calc PR 0.50 A 2
C C10 -0.197(3) 0.8367(11) 0.5551(12) 0.059(3) Uani d PDU 0.50 B 1
H H10A -0.2187 0.8236 0.4935 0.071 Uiso calc PR 0.50 B 1
H H10B -0.3102 0.8732 0.5800 0.071 Uiso calc PR 0.50 B 1
C C11 -0.025(2) 0.9097(17) 0.5692(5) 0.047(2) Uani d PDU 0.50 B 1
H H11A -0.0500 0.9912 0.5570 0.056 Uiso calc PR 0.50 B 1
H H11B 0.0832 0.8835 0.5342 0.056 Uiso calc PR 0.50 B 1
C C10' -0.178(3) 0.8258(11) 0.5408(12) 0.059(3) Uani d PD 0.50 B 2
H H10C -0.3124 0.8465 0.5366 0.071 Uiso calc PR 0.50 B 2
H H10D -0.1312 0.8061 0.4830 0.071 Uiso calc PR 0.50 B 2
C C11' -0.066(2) 0.9241(16) 0.5769(5) 0.047(2) Uani d PD 0.50 B 2
H H11C -0.1475 0.9923 0.5823 0.056 Uiso calc PR 0.50 B 2
H H11D 0.0400 0.9430 0.5384 0.056 Uiso calc PR 0.50 B 2
C C12 0.0096(3) 0.88869(18) 0.66551(14) 0.0339(5) Uani d D 1 . .
H H12 -0.0551 0.9459 0.7027 0.041 Uiso calc PR 0.50 B 1
H H12' -0.0479 0.9394 0.7098 0.041 Uiso calc PR 0.50 B 2
C C13 0.4837(3) 0.8775(2) 0.77691(19) 0.0433(6) Uani d . 1 . .
H H13A 0.5522 0.8322 0.7335 0.052 Uiso calc R 1 . .
H H13B 0.5121 0.8446 0.8337 0.052 Uiso calc R 1 . .
C C14 0.5520(4) 1.0005(2) 0.7740(2) 0.0490(6) Uani d . 1 . .
H H14 0.5020 1.0490 0.7309 0.059 Uiso calc R 1 . .
C C15 0.6751(4) 1.0438(3) 0.8269(2) 0.0565(7) Uani d . 1 . .
H H15A 0.7278 0.9976 0.8707 0.068 Uiso calc R 1 . .
H H15B 0.7119 1.1214 0.8216 0.068 Uiso calc R 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
_geom_angle_publ_flag
C1 N1 C4 . . 124.17(18) ?
C1 N1 C13 . . 116.5(2) ?
C4 N1 C13 . . 118.9(2) ?
C2 N2 C9 . . 122.70(18) ?
C2 N2 C12 . . 124.44(18) ?
C9 N2 C12 . . 112.27(18) ?
O1 C1 N1 . . 121.5(2) ?
O1 C1 C12 . . 123.5(2) ?
N1 C1 C12 . . 115.02(19) ?
O2 C2 N2 . . 122.0(2) ?
O2 C2 C3 . . 121.4(2) ?
N2 C2 C3 . . 116.48(18) ?
C8 C3 C4 . . 118.96(19) ?
C8 C3 C2 . . 115.13(18) ?
C4 C3 C2 . . 125.89(18) ?
C5 C4 C3 . . 118.78(19) ?
C5 C4 N1 . . 118.87(18) ?
C3 C4 N1 . . 122.21(18) ?
C6 C5 C4 . . 121.0(2) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 120.2(2) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 119.1(2) ?
C8 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
C7 C8 C3 . . 121.9(2) ?
C7 C8 H8 . . 119.1 ?
C3 C8 H8 . . 119.1 ?
N2 C9 C10' . . 106.4(8) ?
N2 C9 C10 . . 99.7(8) ?
N2 C9 H9A . . 111.8 ?
C10' C9 H9A . . 115.9 ?
C10 C9 H9A . . 111.8 ?
N2 C9 H9B . . 111.8 ?
C10' C9 H9B . . 100.8 ?
C10 C9 H9B . . 111.8 ?
H9A C9 H9B . . 109.6 ?
N2 C9 H9C . . 110.5 ?
C10' C9 H9C . . 110.5 ?
C10 C9 H9C . . 105.6 ?
H9B C9 H9C . . 116.1 ?
N2 C9 H9D . . 110.5 ?
C10' C9 H9D . . 110.5 ?
C10 C9 H9D . . 121.5 ?
H9A C9 H9D . . 101.8 ?
H9C C9 H9D . . 108.6 ?
C11 C10 C9 . . 104.3(14) ?
C11 C10 H10A . . 110.9 ?
C9 C10 H10A . . 110.9 ?
C11 C10 H10B . . 110.9 ?
C9 C10 H10B . . 110.9 ?
H10A C10 H10B . . 108.9 ?
C10 C11 C12 . . 100.3(12) ?
C10 C11 H11A . . 111.7 ?
C12 C11 H11A . . 111.7 ?
C10 C11 H11B . . 111.7 ?
C12 C11 H11B . . 111.7 ?
H11A C11 H11B . . 109.5 ?
C9 C10' C11' . . 107.4(12) ?
C9 C10' H10C . . 110.2 ?
C11' C10' H10C . . 110.2 ?
C9 C10' H10D . . 110.2 ?
C11' C10' H10D . . 110.2 ?
H10C C10' H10D . . 108.5 ?
C10' C11' C12 . . 108.3(12) ?
C10' C11' H11C . . 110.0 ?
C12 C11' H11C . . 110.0 ?
C10' C11' H11D . . 110.0 ?
C12 C11' H11D . . 110.0 ?
H11C C11' H11D . . 108.4 ?
N2 C12 C1 . . 108.08(19) ?
N2 C12 C11' . . 104.2(8) ?
C1 C12 C11' . . 117.9(7) ?
N2 C12 C11 . . 102.7(8) ?
C1 C12 C11 . . 106.7(6) ?
N2 C12 H12 . . 112.9 ?
C1 C12 H12 . . 112.9 ?
C11' C12 H12 . . 100.6 ?
C11 C12 H12 . . 112.9 ?
N2 C12 H12' . . 108.8 ?
C1 C12 H12' . . 108.8 ?
C11' C12 H12' . . 108.8 ?
C11 C12 H12' . . 121.1 ?
N1 C13 C14 . . 111.7(2) ?
N1 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
N1 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 124.2(3) ?
C15 C14 H14 . . 117.9 ?
C13 C14 H14 . . 117.9 ?
C14 C15 H15A . . 120.0 ?
C14 C15 H15B . . 120.0 ?
H15A C15 H15B . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.224(3) ?
O2 C2 . 1.231(3) ?
N1 C1 . 1.365(3) ?
N1 C4 . 1.418(3) ?
N1 C13 . 1.482(3) ?
N2 C2 . 1.347(3) ?
N2 C9 . 1.470(3) ?
N2 C12 . 1.478(3) ?
C1 C12 . 1.517(4) ?
C2 C3 . 1.499(3) ?
C3 C8 . 1.396(3) ?
C3 C4 . 1.409(3) ?
C4 C5 . 1.402(3) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.395(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.378(3) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C10' . 1.504(7) ?
C9 C10 . 1.510(7) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C9 H9C . 0.9900 ?
C9 H9D . 0.9900 ?
C10 C11 . 1.509(9) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.547(6) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C10' C11' . 1.507(9) ?
C10' H10C . 0.9900 ?
C10' H10D . 0.9900 ?
C11' C12 . 1.545(6) ?
C11' H11C . 0.9900 ?
C11' H11D . 0.9900 ?
C12 H12 . 1.0000 ?
C12 H12' . 1.0000 ?
C13 C14 . 1.522(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.306(4) ?
C14 H14 . 0.9500 ?
C15 H15A . 0.9500 ?
C15 H15B . 0.9500 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 O1 . . . . -180.0(2) ?
C13 N1 C1 O1 . . . . 7.7(3) ?
C4 N1 C1 C12 . . . . -2.2(3) ?
C13 N1 C1 C12 . . . . -174.50(19) ?
C9 N2 C2 O2 . . . . 6.1(3) ?
C12 N2 C2 O2 . . . . 176.6(2) ?
C9 N2 C2 C3 . . . . -169.74(19) ?
C12 N2 C2 C3 . . . . 0.8(3) ?
O2 C2 C3 C8 . . . . -35.3(3) ?
N2 C2 C3 C8 . . . . 140.6(2) ?
O2 C2 C3 C4 . . . . 146.2(2) ?
N2 C2 C3 C4 . . . . -38.0(3) ?
C8 C3 C4 C5 . . . . -1.9(3) ?
C2 C3 C4 C5 . . . . 176.60(19) ?
C8 C3 C4 N1 . . . . 173.72(18) ?
C2 C3 C4 N1 . . . . -7.8(3) ?
C1 N1 C4 C5 . . . . -134.8(2) ?
C13 N1 C4 C5 . . . . 37.4(3) ?
C1 N1 C4 C3 . . . . 49.6(3) ?
C13 N1 C4 C3 . . . . -138.2(2) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
N1 C4 C5 C6 . . . . -176.43(19) ?
C4 C5 C6 C7 . . . . 2.4(3) ?
C5 C6 C7 C8 . . . . -1.4(4) ?
C6 C7 C8 C3 . . . . -1.2(4) ?
C4 C3 C8 C7 . . . . 2.9(3) ?
C2 C3 C8 C7 . . . . -175.8(2) ?
C2 N2 C9 C10' . . . . 159.3(10) ?
C12 N2 C9 C10' . . . . -12.3(10) ?
C2 N2 C9 C10 . . . . 150.1(10) ?
C12 N2 C9 C10 . . . . -21.4(10) ?
N2 C9 C10 C11 . . . . 41.2(14) ?
C10' C9 C10 C11 . . . . -87(8) ?
C9 C10 C11 C12 . . . . -45.3(16) ?
N2 C9 C10' C11' . . . . 11.4(17) ?
C10 C9 C10' C11' . . . . 65(8) ?
C9 C10' C11' C12 . . . . -6.8(19) ?
C2 N2 C12 C1 . . . . 70.3(3) ?
C9 N2 C12 C1 . . . . -118.3(2) ?
C2 N2 C12 C11' . . . . -163.4(7) ?
C9 N2 C12 C11' . . . . 7.9(7) ?
C2 N2 C12 C11 . . . . -177.1(6) ?
C9 N2 C12 C11 . . . . -5.7(6) ?
O1 C1 C12 N2 . . . . 107.3(3) ?
N1 C1 C12 N2 . . . . -70.5(3) ?
O1 C1 C12 C11' . . . . -10.4(9) ?
N1 C1 C12 C11' . . . . 171.8(8) ?
O1 C1 C12 C11 . . . . -2.6(8) ?
N1 C1 C12 C11 . . . . 179.7(8) ?
C10' C11' C12 N2 . . . . -0.5(14) ?
C10' C11' C12 C1 . . . . 119.3(11) ?
C10' C11' C12 C11 . . . . 85(7) ?
C10 C11 C12 N2 . . . . 30.4(12) ?
C10 C11 C12 C1 . . . . 144.0(10) ?
C10 C11 C12 C11' . . . . -68(6) ?
C1 N1 C13 C14 . . . . 73.4(3) ?
C4 N1 C13 C14 . . . . -99.4(3) ?
N1 C13 C14 C15 . . . . 139.5(3) ?
