#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/23/8102336.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_8102336
loop_
_publ_author_name
'Rachid Bouhfid'
'Said Lazar'
'El Mokhtar Essassi'
'Jean-Michel Leger'
'Christian Jarry'
'Gérald Guillaumet'
_publ_section_title
;
 Crystal structure of
 (Z)-1,3-diallyl-4-(2-oxopropylidene)-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one,
 C18H20N2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              435
_journal_volume                  223
_journal_year                    2008
_chemical_formula_iupac          'C18 H20 N2 O2'
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_chemical_name_systematic
;
(Z)-1,3-diallyl-4-(2-oxopropylidene)-4,5-dihydro-1H-1,5-
benzodiazepin-2(3H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.270(10)
_cell_angle_beta                 94.91(2)
_cell_angle_gamma                104.80(3)
_cell_formula_units_Z            2
_cell_length_a                   8.889(4)
_cell_length_b                   9.062(2)
_cell_length_c                   11.0870(10)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.95
_cell_measurement_theta_min      5.25
_cell_volume                     788.7(4)
_computing_cell_refinement       'CAD4 Software (Nonius, 1989)'
_computing_data_collection       'CAD4 Software (Nonius, 1989)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0077
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2648
_diffrn_reflns_theta_full        64.95
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         5.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.8801
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.270(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0894P)²+0.4245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1693
_reflns_number_gt                2540
_reflns_number_total             2648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2381.cff
_cod_data_source_block           I
_cod_database_code               8102336
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.3676(2) -0.3595(2) 0.32058(19) 0.0347(5) Uani 1 1 d . . .
C2 C 0.4453(3) -0.4380(3) 0.2246(2) 0.0472(6) Uani 1 1 d . . .
H2 H 0.4822 -0.3891 0.1678 0.057 Uiso 1 1 calc R . .
C3 C 0.4683(3) -0.5873(3) 0.2127(3) 0.0572(7) Uani 1 1 d . . .
H3 H 0.5208 -0.6378 0.1484 0.069 Uiso 1 1 calc R . .
C4 C 0.4135(3) -0.6616(3) 0.2958(3) 0.0534(6) Uani 1 1 d . . .
H4 H 0.4288 -0.7623 0.2875 0.064 Uiso 1 1 calc R . .
C5 C 0.3365(3) -0.5866(3) 0.3907(2) 0.0444(6) Uani 1 1 d . . .
H5 H 0.3002 -0.6372 0.4467 0.053 Uiso 1 1 calc R . .
C6 C 0.3118(2) -0.4359(2) 0.40481(19) 0.0353(5) Uani 1 1 d . . .
N7 N 0.2377(2) -0.3635(2) 0.50781(17) 0.0381(5) Uani 1 1 d . . .
H7 H 0.2662 -0.3675 0.5824 0.046 Uiso 1 1 calc R . .
C8 C 0.1260(2) -0.2883(2) 0.50140(19) 0.0342(5) Uani 1 1 d D . .
C9 C 0.0838(2) -0.2807(2) 0.36909(19) 0.0359(5) Uani 1 1 d . . .
H9 H 0.0776 -0.3884 0.3005 0.043 Uiso 1 1 calc R . .
C10 C 0.2250(2) -0.1502(2) 0.36084(18) 0.0348(5) Uani 1 1 d . . .
N11 N 0.35686(19) -0.19944(19) 0.33602(16) 0.0350(5) Uani 1 1 d . . .
C12 C 0.0604(2) -0.2232(3) 0.6083(2) 0.0390(5) Uani 1 1 d . . .
H12 H -0.0116 -0.1669 0.6008 0.047 Uiso 1 1 calc R . .
C13 C 0.0971(3) -0.2377(3) 0.7306(2) 0.0441(6) Uani 1 1 d . . .
C14 C 0.0188(4) -0.1610(4) 0.8415(3) 0.0659(8) Uani 1 1 d . . .
H14A H -0.0431 -0.2462 0.8651 0.099 Uiso 1 1 calc R . .
H14B H -0.0491 -0.1073 0.8138 0.099 Uiso 1 1 calc R . .
H14C H 0.0986 -0.0804 0.9165 0.099 Uiso 1 1 calc R . .
O15 O 0.1920(2) -0.3115(2) 0.74951(16) 0.0564(5) Uani 1 1 d . . .
C16 C -0.0730(3) -0.2473(3) 0.3425(2) 0.0463(6) Uani 1 1 d D . .
H16A H -0.1573 -0.3262 0.3582 0.056 Uiso 1 1 calc R . .
H16B H -0.0660 -0.1363 0.4035 0.056 Uiso 1 1 calc R . .
C17 C -0.1128(4) -0.2617(5) 0.2055(3) 0.0735(9) Uani 1 1 d D . .
H17 H -0.1034 -0.1598 0.2001 0.088 Uiso 1 1 calc R . .
C18 C -0.1537(8) -0.3746(7) 0.1021(4) 0.148(2) Uani 1 1 d D . .
H18A H -0.1667 -0.4821 0.0966 0.177 Uiso 1 1 calc R . .
H18B H -0.1731 -0.3564 0.0257 0.177 Uiso 1 1 calc R . .
O19 O 0.22396(19) -0.00934(18) 0.37935(16) 0.0489(5) Uani 1 1 d . . .
C20 C 0.4936(3) -0.0803(3) 0.3215(2) 0.0423(5) Uani 1 1 d . . .
H20A H 0.5886 -0.1078 0.3417 0.051 Uiso 1 1 calc R . .
H20B H 0.5049 0.0301 0.3861 0.051 Uiso 1 1 calc R . .
C21 C 0.4836(3) -0.0755(3) 0.1879(2) 0.0514(6) Uani 1 1 d . . .
H21 H 0.5732 -0.0089 0.1740 0.062 Uiso 1 1 calc R . .
C22 C 0.3655(4) -0.1527(4) 0.0901(3) 0.0659(8) Uani 1 1 d . . .
H22A H 0.2728 -0.2210 0.0984 0.079 Uiso 1 1 calc R . .
H22B H 0.3727 -0.1402 0.0109 0.079 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C6 118.66(18) . . ?
C2 C1 N11 119.13(18) . . ?
C6 C1 N11 122.07(17) . . ?
C3 C2 C1 121.0(2) . . ?
C4 C3 C2 120.1(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 121.1(2) . . ?
C5 C6 C1 119.25(19) . . ?
C5 C6 N7 117.77(18) . . ?
C1 C6 N7 122.91(17) . . ?
C8 N7 C6 126.50(17) . . ?
N7 C8 C12 121.47(18) . . ?
N7 C8 C9 114.37(16) . . ?
C12 C8 C9 124.15(17) . . ?
C8 C9 C10 105.66(16) . . ?
C8 C9 C16 116.00(16) . . ?
C10 C9 C16 112.31(17) . . ?
O19 C10 N11 121.72(19) . . ?
O19 C10 C9 122.74(18) . . ?
N11 C10 C9 115.50(16) . . ?
C10 N11 C1 124.13(17) . . ?
C10 N11 C20 117.47(17) . . ?
C1 N11 C20 118.39(16) . . ?
C8 C12 C13 123.21(19) . . ?
O15 C13 C12 122.80(19) . . ?
O15 C13 C14 118.4(2) . . ?
C12 C13 C14 118.7(2) . . ?
C17 C16 C9 111.9(2) . . ?
C18 C17 C16 133.6(4) . . ?
N11 C20 C21 114.92(18) . . ?
C22 C21 C20 127.4(2) . . ?
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
C1 C2 1.394(3) . ?
C1 C6 1.403(3) . ?
C1 N11 1.427(2) . ?
C2 C3 1.380(3) . ?
C3 C4 1.378(4) . ?
C4 C5 1.371(3) . ?
C5 C6 1.394(3) . ?
C6 N7 1.405(3) . ?
N7 C8 1.351(3) . ?
C8 C12 1.371(3) . ?
C8 C9 1.513(3) . ?
C9 C10 1.524(3) . ?
C9 C16 1.527(3) . ?
C10 O19 1.220(2) . ?
C10 N11 1.372(3) . ?
N11 C20 1.469(3) . ?
C12 C13 1.427(3) . ?
C13 O15 1.250(3) . ?
C13 C14 1.501(3) . ?
C16 C17 1.480(4) . ?
C17 C18 1.175(5) . ?
C20 C21 1.494(3) . ?
C21 C22 1.284(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N7 H7 O15 0.860 1.955 2.634(2) 134
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
N11 C1 C2 C3 175.3(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 N7 -177.5(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N11 C1 C6 C5 -175.21(17) . . . . ?
C2 C1 C6 N7 177.45(19) . . . . ?
N11 C1 C6 N7 1.8(3) . . . . ?
C5 C6 N7 C8 -138.9(2) . . . . ?
C1 C6 N7 C8 44.0(3) . . . . ?
C6 N7 C8 C12 179.31(18) . . . . ?
C6 N7 C8 C9 -1.6(3) . . . . ?
N7 C8 C9 C10 -73.0(2) . . . . ?
C12 C8 C9 C10 106.1(2) . . . . ?
N7 C8 C9 C16 161.88(18) . . . . ?
C12 C8 C9 C16 -19.1(3) . . . . ?
C8 C9 C10 O19 -102.4(2) . . . . ?
C16 C9 C10 O19 24.9(3) . . . . ?
C8 C9 C10 N11 75.1(2) . . . . ?
C16 C9 C10 N11 -157.48(17) . . . . ?
O19 C10 N11 C1 176.55(17) . . . . ?
C9 C10 N11 C1 -1.1(3) . . . . ?
O19 C10 N11 C20 -5.0(3) . . . . ?
C9 C10 N11 C20 177.42(16) . . . . ?
C2 C1 N11 C10 140.6(2) . . . . ?
C6 C1 N11 C10 -43.7(3) . . . . ?
C2 C1 N11 C20 -37.8(3) . . . . ?
C6 C1 N11 C20 137.78(19) . . . . ?
N7 C8 C12 C13 -3.7(3) . . . . ?
C9 C8 C12 C13 177.35(19) . . . . ?
C8 C12 C13 O15 -0.2(3) . . . . ?
C8 C12 C13 C14 179.7(2) . . . . ?
C8 C9 C16 C17 -173.3(2) . . . . ?
C10 C9 C16 C17 65.0(3) . . . . ?
C9 C16 C17 C18 71.0(6) . . . . ?
C10 N11 C20 C21 -82.1(2) . . . . ?
C1 N11 C20 C21 96.5(2) . . . . ?
N11 C20 C21 C22 6.0(4) . . . . ?
