#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232851.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_2232851
loop_
_publ_author_name
'Rida, Mohamed'
'Alsubari, Abdusalam'
'Essassi, El Mokhtar'
'Zouihri, Hafid'
'Ng, Seik Weng'
_publ_section_title
;
 5-Acetyl-3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one
;
_journal_coeditor_code           LH5376
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3337
_journal_paper_doi               10.1107/S1600536811047878
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H16 N2 O3'
_chemical_formula_moiety         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_chemical_name_systematic
;
5-Acetyl-3-hydroxy-4-phenyl-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                81.5630(10)
_cell_angle_beta                 68.9210(10)
_cell_angle_gamma                80.1460(10)
_cell_formula_units_Z            2
_cell_length_a                   8.97100(10)
_cell_length_b                   9.31420(10)
_cell_length_c                   9.41290(10)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.45
_cell_measurement_theta_min      2.23
_cell_volume                     719.954(14)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_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    0.0158
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19110
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0473
_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)+(0.0876P)²+0.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                3584
_reflns_number_total             4203
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5376.cif
_cod_data_source_block           I
_cod_database_code               2232851
_cod_database_fobs_code          2232851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.18813(12) 0.41278(9) 0.39332(11) 0.0488(2) Uani d . 1 1
O O2 0.50968(12) 0.39185(9) 0.34285(10) 0.0430(2) Uani d . 1 1
O O3 0.41433(13) 0.74792(11) -0.06449(10) 0.0513(2) Uani d . 1 1
N N1 0.14350(13) 0.64817(10) 0.44597(12) 0.0426(2) Uani d . 1 1
N N2 0.37829(11) 0.75893(9) 0.18338(9) 0.03178(19) Uani d . 1 1
C C1 0.19921(15) 0.78134(12) 0.44620(13) 0.0406(3) Uani d . 1 1
C C2 0.1358(2) 0.85962(16) 0.57413(16) 0.0656(5) Uani d . 1 1
H H2A 0.0547 0.8253 0.6599 0.079 Uiso calc R 1 1
C C3 0.1927(3) 0.98823(18) 0.5745(2) 0.0756(6) Uani d . 1 1
H H3 0.1499 1.0396 0.6609 0.091 Uiso calc R 1 1
C C4 0.3123(2) 1.04144(16) 0.4483(2) 0.0639(4) Uani d . 1 1
H H4 0.3501 1.1280 0.4496 0.077 Uiso calc R 1 1
C C5 0.37548(17) 0.96508(13) 0.31996(15) 0.0468(3) Uani d . 1 1
H H5 0.4570 0.9999 0.2349 0.056 Uiso calc R 1 1
C C6 0.31790(13) 0.83653(11) 0.31723(12) 0.0346(2) Uani d . 1 1
C C7 0.24114(14) 0.52550(11) 0.39399(12) 0.0363(2) Uani d . 1 1
C C8 0.42230(13) 0.53221(11) 0.34285(11) 0.0329(2) Uani d . 1 1
H H8 0.4407 0.5843 0.4171 0.039 Uiso calc R 1 1
C C9 0.48415(12) 0.61900(10) 0.18549(10) 0.0293(2) Uani d . 1 1
H H9 0.4758 0.5617 0.1099 0.035 Uiso calc R 1 1
C C10 0.65889(13) 0.64317(11) 0.13784(12) 0.0345(2) Uani d . 1 1
C C11 0.72509(17) 0.67606(14) 0.24003(18) 0.0493(3) Uani d . 1 1
H H11 0.6625 0.6825 0.3425 0.059 Uiso calc R 1 1
C C12 0.8864(2) 0.69927(17) 0.1874(3) 0.0685(5) Uani d . 1 1
H H12 0.9311 0.7212 0.2555 0.082 Uiso calc R 1 1
C C13 0.98046(18) 0.69010(16) 0.0359(3) 0.0722(6) Uani d . 1 1
H H13 1.0876 0.7066 0.0020 0.087 Uiso calc R 1 1
C C14 0.91519(18) 0.65653(16) -0.0649(2) 0.0624(4) Uani d . 1 1
H H14 0.9786 0.6493 -0.1671 0.075 Uiso calc R 1 1
C C15 0.75549(15) 0.63361(13) -0.01454(15) 0.0450(3) Uani d . 1 1
H H15 0.7120 0.6115 -0.0835 0.054 Uiso calc R 1 1
C C16 0.35154(14) 0.81314(12) 0.05077(12) 0.0371(2) Uani d . 1 1
C C17 0.24042(18) 0.95367(15) 0.05114(17) 0.0529(3) Uani d . 1 1
H H17A 0.1983 0.9597 -0.0303 0.079 Uiso calc R 1 1
H H17B 0.2988 1.0350 0.0367 0.079 Uiso calc R 1 1
H H17C 0.1532 0.9560 0.1472 0.079 Uiso calc R 1 1
H H1 0.042(2) 0.635(2) 0.498(2) 0.057(5) Uiso d . 1 1
H H2 0.517(2) 0.353(2) 0.266(2) 0.065(5) Uiso d . 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
C8 O2 H2 109.8(14)
C7 N1 C1 124.00(10)
C7 N1 H1 114.4(12)
C1 N1 H1 120.4(12)
C16 N2 C6 122.88(9)
C16 N2 C9 118.55(8)
C6 N2 C9 118.41(8)
C2 C1 C6 119.01(11)
C2 C1 N1 120.58(11)
C6 C1 N1 120.40(10)
C3 C2 C1 120.25(13)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C4 C3 C2 120.84(13)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.44(13)
C3 C4 H4 120.3
C5 C4 H4 120.3
C4 C5 C6 120.37(12)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 120.05(10)
C5 C6 N2 121.01(10)
C1 C6 N2 118.94(9)
O1 C7 N1 122.08(11)
O1 C7 C8 121.49(10)
N1 C7 C8 116.36(9)
O2 C8 C7 111.68(8)
O2 C8 C9 110.91(8)
C7 C8 C9 111.53(9)
O2 C8 H8 107.5
C7 C8 H8 107.5
C9 C8 H8 107.5
N2 C9 C10 111.43(8)
N2 C9 C8 109.66(8)
C10 C9 C8 113.46(9)
N2 C9 H9 107.3
C10 C9 H9 107.3
C8 C9 H9 107.3
C11 C10 C15 119.09(12)
C11 C10 C9 122.52(10)
C15 C10 C9 118.38(10)
C10 C11 C12 119.33(15)
C10 C11 H11 120.3
C12 C11 H11 120.3
C13 C12 C11 120.92(16)
C13 C12 H12 119.5
C11 C12 H12 119.5
C14 C13 C12 119.71(14)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.03(16)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C10 120.91(14)
C14 C15 H15 119.5
C10 C15 H15 119.5
O3 C16 N2 120.90(10)
O3 C16 C17 121.05(11)
N2 C16 C17 118.04(10)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2261(13)
O2 C8 1.4046(13)
O2 H2 0.83(2)
O3 C16 1.2247(14)
N1 C7 1.3510(15)
N1 C1 1.4149(14)
N1 H1 0.89(2)
N2 C16 1.3637(14)
N2 C6 1.4302(13)
N2 C9 1.4776(12)
C1 C2 1.3886(17)
C1 C6 1.3950(15)
C2 C3 1.381(2)
C2 H2A 0.9300
C3 C4 1.378(3)
C3 H3 0.9300
C4 C5 1.3814(19)
C4 H4 0.9300
C5 C6 1.3897(15)
C5 H5 0.9300
C7 C8 1.5297(16)
C8 C9 1.5382(13)
C8 H8 0.9800
C9 C10 1.5148(14)
C9 H9 0.9800
C10 C11 1.3897(17)
C10 C15 1.3905(16)
C11 C12 1.395(2)
C11 H11 0.9300
C12 C13 1.378(3)
C12 H12 0.9300
C13 C14 1.375(3)
C13 H13 0.9300
C14 C15 1.3818(19)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.5031(17)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
N1 H1 O1 2_566 0.89(2) 2.04(2) 2.9240(10) 175(2)
O2 H2 O3 2_665 0.83(2) 2.09(2) 2.9050(10) 168(2)
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
C7 N1 C1 C2 -134.65(15)
C7 N1 C1 C6 45.87(19)
C6 C1 C2 C3 -1.6(3)
N1 C1 C2 C3 178.87(17)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 0.1(3)
C3 C4 C5 C6 0.7(3)
C4 C5 C6 C1 -2.0(2)
C4 C5 C6 N2 177.86(14)
C2 C1 C6 C5 2.5(2)
N1 C1 C6 C5 -178.04(12)
C2 C1 C6 N2 -177.42(13)
N1 C1 C6 N2 2.06(18)
C16 N2 C6 C5 -67.48(16)
C9 N2 C6 C5 107.89(12)
C16 N2 C6 C1 112.42(13)
C9 N2 C6 C1 -72.21(14)
C1 N1 C7 O1 -178.75(11)
C1 N1 C7 C8 4.08(17)
O1 C7 C8 O2 -18.12(14)
N1 C7 C8 O2 159.07(10)
O1 C7 C8 C9 106.61(11)
N1 C7 C8 C9 -76.20(12)
C16 N2 C9 C10 88.48(11)
C6 N2 C9 C10 -87.10(10)
C16 N2 C9 C8 -145.05(10)
C6 N2 C9 C8 39.37(12)
O2 C8 C9 N2 173.40(8)
C7 C8 C9 N2 48.24(11)
O2 C8 C9 C10 -61.29(11)
C7 C8 C9 C10 173.56(8)
N2 C9 C10 C11 84.57(12)
C8 C9 C10 C11 -39.79(14)
N2 C9 C10 C15 -94.64(11)
C8 C9 C10 C15 140.99(10)
C15 C10 C11 C12 0.26(18)
C9 C10 C11 C12 -178.95(11)
C10 C11 C12 C13 0.0(2)
C11 C12 C13 C14 -0.5(2)
C12 C13 C14 C15 0.7(2)
C13 C14 C15 C10 -0.4(2)
C11 C10 C15 C14 -0.10(18)
C9 C10 C15 C14 179.14(11)
C6 N2 C16 O3 175.01(10)
C9 N2 C16 O3 -0.35(16)
C6 N2 C16 C17 -6.10(16)
C9 N2 C16 C17 178.53(10)
