#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/51/2225163.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_2225163
loop_
_publ_author_name
'Nichol, Gary S.'
'Gunawan, Steven'
'Dietrich, Justin'
'Hulme, Christopher'
_publ_section_title
2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1,3(2H)-dione
_journal_coeditor_code           BH2272
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o625
_journal_paper_doi               10.1107/S1600536810005477
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H21 N3 O2'
_chemical_formula_moiety         'C21 H21 N3 O2'
_chemical_formula_sum            'C21 H21 N3 O2'
_chemical_formula_weight         347.41
_chemical_name_systematic
;
2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a]
[1,4]diazepine-1,3(2H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.494(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.192(4)
_cell_length_b                   7.638(2)
_cell_length_c                   18.514(6)
_cell_measurement_reflns_used    2525
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.84
_cell_measurement_theta_min      2.21
_cell_volume                     1716.1(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14047
_diffrn_reflns_theta_full        24.11
_diffrn_reflns_theta_max         24.11
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.286
_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_constraints    0
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1146P)²+0.6555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1808
_reflns_number_gt                1908
_reflns_number_total             2724
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2272.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225163
_cod_database_fobs_code          2225163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.88328(17) 0.0841(3) 0.87585(11) 0.0267(6) Uani d . 1 . .
O O2 0.61570(19) 0.1425(3) 1.03172(11) 0.0346(6) Uani d . 1 . .
N N1 0.7648(2) 0.0891(4) 0.96528(13) 0.0249(6) Uani d . 1 . .
N N2 0.62702(19) 0.2468(3) 0.91468(13) 0.0221(6) Uani d . 1 . .
N N3 0.6120(2) 0.4044(4) 0.76450(14) 0.0253(7) Uani d . 1 . .
H H3N 0.625(3) 0.466(5) 0.7271(19) 0.030 Uiso d . 1 . .
C C1 0.7968(3) 0.1375(4) 0.89869(16) 0.0243(8) Uani d . 1 . .
C C2 0.6618(3) 0.1580(5) 0.97655(17) 0.0282(8) Uani d . 1 . .
C C3 0.5292(3) 0.3561(5) 0.90814(17) 0.0290(8) Uani d . 1 . .
H H3A 0.5519 0.4803 0.9130 0.035 Uiso calc R 1 . .
H H3B 0.4843 0.3285 0.9485 0.035 Uiso calc R 1 . .
C C4 0.4598(2) 0.3329(5) 0.83796(17) 0.0272(8) Uani d . 1 . .
C C5 0.3498(3) 0.2811(5) 0.83711(18) 0.0308(8) Uani d . 1 . .
H H5 0.3222 0.2501 0.8816 0.037 Uiso calc R 1 . .
C C6 0.2800(3) 0.2733(5) 0.77408(18) 0.0316(8) Uani d . 1 . .
H H6 0.2060 0.2351 0.7752 0.038 Uiso calc R 1 . .
C C7 0.3188(3) 0.3216(5) 0.70925(18) 0.0295(8) Uani d . 1 . .
H H7 0.2707 0.3223 0.6658 0.035 Uiso calc R 1 . .
C C8 0.4285(3) 0.3690(4) 0.70802(17) 0.0274(8) Uani d . 1 . .
H H8 0.4551 0.4017 0.6634 0.033 Uiso calc R 1 . .
C C9 0.4995(2) 0.3694(4) 0.77089(17) 0.0241(8) Uani d . 1 . .
C C10 0.7038(2) 0.3312(4) 0.80057(16) 0.0239(8) Uani d . 1 . .
C C11 0.7095(2) 0.2491(4) 0.86567(16) 0.0215(7) Uani d . 1 . .
C C12 0.8299(3) -0.0207(5) 1.01778(16) 0.0291(8) Uani d . 1 . .
H H12A 0.8060 0.0008 1.0666 0.035 Uiso calc R 1 . .
H H12B 0.9083 0.0136 1.0189 0.035 Uiso calc R 1 . .
C C13 0.8194(3) -0.2160(5) 1.00075(16) 0.0290(8) Uani d . 1 . .
H H13A 0.7411 -0.2509 0.9997 0.035 Uiso calc R 1 . .
H H13B 0.8435 -0.2381 0.9520 0.035 Uiso calc R 1 . .
C C14 0.8874(3) -0.3268(5) 1.05583(17) 0.0297(8) Uani d . 1 . .
H H14A 0.8702 -0.2937 1.1052 0.036 Uiso calc R 1 . .
H H14B 0.9666 -0.3032 1.0523 0.036 Uiso calc R 1 . .
C C15 0.8653(3) -0.5210(5) 1.04422(19) 0.0377(9) Uani d . 1 . .
H H15A 0.7890 -0.5471 1.0531 0.057 Uiso calc R 1 . .
H H15B 0.9157 -0.5887 1.0779 0.057 Uiso calc R 1 . .
H H15C 0.8768 -0.5525 0.9942 0.057 Uiso calc R 1 . .
C C16 0.8047(2) 0.3506(4) 0.76174(16) 0.0231(7) Uani d . 1 . .
C C17 0.8030(2) 0.2989(5) 0.68966(16) 0.0256(8) Uani d . 1 . .
H H17 0.7377 0.2506 0.6654 0.031 Uiso calc R 1 . .
C C18 0.8963(3) 0.3177(5) 0.65308(16) 0.0279(8) Uani d . 1 . .
H H18 0.8943 0.2830 0.6037 0.033 Uiso calc R 1 . .
C C19 0.9920(3) 0.3863(5) 0.68772(17) 0.0292(8) Uani d . 1 . .
H H19 1.0559 0.3979 0.6625 0.035 Uiso calc R 1 . .
C C20 0.9944(3) 0.4382(4) 0.75934(17) 0.0272(8) Uani d . 1 . .
H H20 1.0601 0.4852 0.7835 0.033 Uiso calc R 1 . .
C C21 0.9005(2) 0.4217(4) 0.79611(17) 0.0256(8) Uani d . 1 . .
H H21 0.9022 0.4594 0.8451 0.031 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 C2 . . 111.6(3) ?
C1 N1 C12 . . 124.5(3) ?
C2 N1 C12 . . 123.8(2) ?
C2 N2 C3 . . 122.9(2) ?
C2 N2 C11 . . 111.2(2) ?
C3 N2 C11 . . 124.5(3) ?
H3N N3 C9 . . 115(2) ?
H3N N3 C10 . . 115(2) ?
C9 N3 C10 . . 129.6(3) ?
O1 C1 N1 . . 122.6(3) ?
O1 C1 C11 . . 131.4(3) ?
N1 C1 C11 . . 105.9(3) ?
O2 C2 N1 . . 125.6(3) ?
O2 C2 N2 . . 128.5(3) ?
N1 C2 N2 . . 105.9(2) ?
N2 C3 H3A . . 108.9 ?
N2 C3 H3B . . 108.9 ?
N2 C3 C4 . . 113.4(3) ?
H3A C3 H3B . . 107.7 ?
H3A C3 C4 . . 108.9 ?
H3B C3 C4 . . 108.9 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 C9 . . 122.2(3) ?
C5 C4 C9 . . 117.3(3) ?
C4 C5 H5 . . 118.8 ?
C4 C5 C6 . . 122.5(3) ?
H5 C5 C6 . . 118.8 ?
C5 C6 H6 . . 120.4 ?
C5 C6 C7 . . 119.2(3) ?
H6 C6 C7 . . 120.4 ?
C6 C7 H7 . . 120.2 ?
C6 C7 C8 . . 119.7(3) ?
H7 C7 C8 . . 120.2 ?
C7 C8 H8 . . 119.6 ?
C7 C8 C9 . . 120.9(3) ?
H8 C8 C9 . . 119.6 ?
N3 C9 C4 . . 122.1(3) ?
N3 C9 C8 . . 117.7(3) ?
C4 C9 C8 . . 120.2(3) ?
N3 C10 C11 . . 126.4(3) ?
N3 C10 C16 . . 113.5(3) ?
C11 C10 C16 . . 120.1(3) ?
N2 C11 C1 . . 105.0(2) ?
N2 C11 C10 . . 126.6(3) ?
C1 C11 C10 . . 128.3(3) ?
N1 C12 H12A . . 108.9 ?
N1 C12 H12B . . 108.9 ?
N1 C12 C13 . . 113.2(3) ?
H12A C12 H12B . . 107.7 ?
H12A C12 C13 . . 108.9 ?
H12B C12 C13 . . 108.9 ?
C12 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C12 C13 C14 . . 112.2(3) ?
H13A C13 H13B . . 107.9 ?
H13A C13 C14 . . 109.2 ?
H13B C13 C14 . . 109.2 ?
C13 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C13 C14 C15 . . 111.9(3) ?
H14A C14 H14B . . 107.9 ?
H14A C14 C15 . . 109.2 ?
H14B C14 C15 . . 109.2 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15B . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C10 C16 C17 . . 119.8(3) ?
C10 C16 C21 . . 121.0(3) ?
C17 C16 C21 . . 119.1(3) ?
C16 C17 H17 . . 119.9 ?
C16 C17 C18 . . 120.1(3) ?
H17 C17 C18 . . 119.9 ?
C17 C18 H18 . . 119.7 ?
C17 C18 C19 . . 120.6(3) ?
H18 C18 C19 . . 119.7 ?
C18 C19 H19 . . 120.2 ?
C18 C19 C20 . . 119.6(3) ?
H19 C19 C20 . . 120.2 ?
C19 C20 H20 . . 120.0 ?
C19 C20 C21 . . 120.1(3) ?
H20 C20 C21 . . 120.0 ?
C16 C21 C20 . . 120.5(3) ?
C16 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
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 . 1.241(4) ?
O2 C2 . 1.218(4) ?
N1 C1 . 1.379(4) ?
N1 C2 . 1.396(4) ?
N1 C12 . 1.459(4) ?
N2 C2 . 1.363(4) ?
N2 C3 . 1.452(4) ?
N2 C11 . 1.417(4) ?
N3 H3N . 0.86(4) ?
N3 C9 . 1.413(4) ?
N3 C10 . 1.367(4) ?
C1 C11 . 1.453(5) ?
C3 H3A . 0.990 ?
C3 H3B . 0.990 ?
C3 C4 . 1.492(5) ?
C4 C5 . 1.396(5) ?
C4 C9 . 1.403(4) ?
C5 H5 . 0.950 ?
C5 C6 . 1.379(5) ?
C6 H6 . 0.950 ?
C6 C7 . 1.382(5) ?
C7 H7 . 0.950 ?
C7 C8 . 1.387(4) ?
C8 H8 . 0.950 ?
C8 C9 . 1.383(5) ?
C10 C11 . 1.355(4) ?
C10 C16 . 1.491(4) ?
C12 H12A . 0.990 ?
C12 H12B . 0.990 ?
C12 C13 . 1.528(5) ?
C13 H13A . 0.990 ?
C13 H13B . 0.990 ?
C13 C14 . 1.510(5) ?
C14 H14A . 0.990 ?
C14 H14B . 0.990 ?
C14 C15 . 1.519(5) ?
C15 H15A . 0.980 ?
C15 H15B . 0.980 ?
C15 H15C . 0.980 ?
C16 C17 . 1.390(4) ?
C16 C21 . 1.387(5) ?
C17 H17 . 0.950 ?
C17 C18 . 1.386(4) ?
C18 H18 . 0.950 ?
C18 C19 . 1.380(5) ?
C19 H19 . 0.950 ?
C19 C20 . 1.381(5) ?
C20 H20 . 0.950 ?
C20 C21 . 1.392(4) ?
C21 H21 . 0.950 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3N O1 2_656 0.86(4) 2.10(4) 2.944(3) 165(3) yes
C8 H8 O1 2_656 0.95 2.57 3.326(4) 136.3 yes
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
C2 N1 C1 O1 . . . . -176.4(3) ?
C2 N1 C1 C11 . . . . 1.5(4) ?
C12 N1 C1 O1 . . . . 3.5(5) ?
C12 N1 C1 C11 . . . . -178.5(3) ?
C3 N2 C2 O2 . . . . 6.5(5) ?
C3 N2 C2 N1 . . . . -172.0(3) ?
C11 N2 C2 O2 . . . . 173.7(3) ?
C11 N2 C2 N1 . . . . -4.8(4) ?
C1 N1 C2 O2 . . . . -176.7(3) ?
C1 N1 C2 N2 . . . . 2.0(4) ?
C12 N1 C2 O2 . . . . 3.4(5) ?
C12 N1 C2 N2 . . . . -178.0(3) ?
C2 N2 C3 C4 . . . . -136.8(3) ?
C11 N2 C3 C4 . . . . 57.7(4) ?
N2 C3 C4 C5 . . . . 121.8(3) ?
N2 C3 C4 C9 . . . . -61.3(4) ?
C3 C4 C5 C6 . . . . 174.0(3) ?
C9 C4 C5 C6 . . . . -3.1(5) ?
C4 C5 C6 C7 . . . . -1.3(5) ?
C5 C6 C7 C8 . . . . 3.1(5) ?
C6 C7 C8 C9 . . . . -0.3(5) ?
C7 C8 C9 N3 . . . . 174.6(3) ?
C7 C8 C9 C4 . . . . -4.3(5) ?
C3 C4 C9 N3 . . . . 9.9(5) ?
C3 C4 C9 C8 . . . . -171.2(3) ?
C5 C4 C9 N3 . . . . -173.1(3) ?
C5 C4 C9 C8 . . . . 5.8(5) ?
C10 N3 C9 C4 . . . . 37.7(5) ?
C10 N3 C9 C8 . . . . -141.3(3) ?
C9 N3 C10 C11 . . . . -22.3(6) ?
C9 N3 C10 C16 . . . . 158.5(3) ?
N3 C10 C11 N2 . . . . -10.9(6) ?
N3 C10 C11 C1 . . . . 165.3(3) ?
C16 C10 C11 N2 . . . . 168.2(3) ?
C16 C10 C11 C1 . . . . -15.6(5) ?
C2 N2 C11 C1 . . . . 5.7(4) ?
C2 N2 C11 C10 . . . . -177.3(3) ?
C3 N2 C11 C1 . . . . 172.7(3) ?
C3 N2 C11 C10 . . . . -10.4(5) ?
O1 C1 C11 N2 . . . . 173.5(3) ?
O1 C1 C11 C10 . . . . -3.4(6) ?
N1 C1 C11 N2 . . . . -4.2(3) ?
N1 C1 C11 C10 . . . . 178.9(3) ?
C1 N1 C12 C13 . . . . -80.8(4) ?
C2 N1 C12 C13 . . . . 99.1(3) ?
N1 C12 C13 C14 . . . . -180.0(2) ?
C12 C13 C14 C15 . . . . 172.6(3) ?
N3 C10 C16 C17 . . . . -52.2(4) ?
N3 C10 C16 C21 . . . . 127.0(3) ?
C11 C10 C16 C17 . . . . 128.6(3) ?
C11 C10 C16 C21 . . . . -52.2(5) ?
C10 C16 C17 C18 . . . . 179.6(3) ?
C21 C16 C17 C18 . . . . 0.3(5) ?
C16 C17 C18 C19 . . . . 0.5(5) ?
C17 C18 C19 C20 . . . . -0.6(5) ?
C18 C19 C20 C21 . . . . -0.2(5) ?
C10 C16 C21 C20 . . . . 179.7(3) ?
C17 C16 C21 C20 . . . . -1.1(5) ?
C19 C20 C21 C16 . . . . 1.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744510
