#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238018.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_2238018
loop_
_publ_author_name
'Belaziz, Dounia'
'Kandri Rodi, Youssef'
'Kandri Rodi, Adiba'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 Ethyl
 2-oxo-3-(3-phthalimidopropyl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxylate
;
_journal_coeditor_code           SJ5310
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o641
_journal_page_last               o642
_journal_paper_doi               10.1107/S1600536813008325
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C21 H19 N3 O5'
_chemical_formula_moiety         'C21 H19 N3 O5'
_chemical_formula_sum            'C21 H19 N3 O5'
_chemical_formula_weight         393.39
_chemical_name_systematic
'Ethyl 2-oxo-3-(3-phthalimidopropyl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxylate'
_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                86.454(7)
_cell_angle_beta                 83.424(8)
_cell_angle_gamma                89.376(7)
_cell_formula_units_Z            2
_cell_length_a                   5.2850(7)
_cell_length_b                   10.6663(12)
_cell_length_c                   16.505(2)
_cell_measurement_reflns_used    3384
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.24
_cell_volume                     922.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEXII area-detector'
_diffrn_measurement_method       'φ and 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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19211
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.381
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.3912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1450
_reflns_number_gt                2405
_reflns_number_total             3384
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5310.cif
_cod_data_source_block           I
_cod_database_code               2238018
_cod_database_fobs_code          2238018
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
C C5 -0.2365(7) 0.1185(3) -0.2119(2) 0.0843(10) Uani d . 1 1
H H5 -0.3437 0.0758 -0.2415 0.101 Uiso calc R 1 1
C C21 -0.3239(7) 0.4211(3) 0.6009(2) 0.0908(10) Uani d . 1 1
H H21B -0.4152 0.4241 0.6545 0.136 Uiso calc R 1 1
H H21A -0.3239 0.5030 0.5734 0.136 Uiso calc R 1 1
H H21C -0.1516 0.3946 0.6055 0.136 Uiso calc R 1 1
N N2 0.2008(4) 0.34071(17) 0.26388(11) 0.0470(5) Uani d . 1 1
N N3 0.0386(4) 0.26952(18) 0.38811(11) 0.0523(5) Uani d . 1 1
N N1 0.1200(4) 0.24930(18) 0.00965(11) 0.0510(5) Uani d . 1 1
C C12 0.3548(4) 0.2414(2) 0.28783(13) 0.0443(5) Uani d . 1 1
C C2 0.0804(5) 0.2455(2) -0.12718(14) 0.0500(6) Uani d . 1 1
O O3 -0.1555(4) 0.44303(17) 0.32188(11) 0.0689(5) Uani d . 1 1
C C17 0.2542(4) 0.1945(2) 0.36512(13) 0.0469(6) Uani d . 1 1
C C10 0.1307(5) 0.3982(2) 0.11910(14) 0.0507(6) Uani d . 1 1
H H10A -0.0524 0.3959 0.1337 0.061 Uiso calc R 1 1
H H10B 0.1674 0.4644 0.0765 0.061 Uiso calc R 1 1
C C7 -0.1005(4) 0.1658(2) -0.08645(15) 0.0506(6) Uani d . 1 1
O O5 -0.2966(4) 0.3344(2) 0.47224(11) 0.0810(6) Uani d . 1 1
O O4 -0.0387(4) 0.1848(2) 0.51828(11) 0.0833(6) Uani d . 1 1
C C8 -0.0771(5) 0.1668(2) 0.00225(15) 0.0522(6) Uani d . 1 1
O O2 -0.1989(4) 0.10977(18) 0.05886(12) 0.0750(6) Uani d . 1 1
C C18 0.0058(5) 0.3619(2) 0.32393(14) 0.0520(6) Uani d . 1 1
C C1 0.2254(5) 0.3000(2) -0.06647(15) 0.0526(6) Uani d . 1 1
C C11 0.2575(5) 0.4292(2) 0.19332(13) 0.0504(6) Uani d . 1 1
H H11A 0.4404 0.4313 0.1785 0.060 Uiso calc R 1 1
H H11B 0.2036 0.5125 0.2088 0.060 Uiso calc R 1 1
C C16 0.3660(5) 0.0934(2) 0.40379(15) 0.0582(7) Uani d . 1 1
H H16 0.2968 0.0601 0.4548 0.070 Uiso calc R 1 1
O O1 0.4014(4) 0.37287(19) -0.07584(12) 0.0772(6) Uani d . 1 1
C C19 -0.0985(6) 0.2572(3) 0.46572(16) 0.0624(7) Uani d . 1 1
C C9 0.2183(5) 0.2738(2) 0.08601(15) 0.0572(6) Uani d . 1 1
H H9A 0.4030 0.2727 0.0774 0.069 Uiso calc R 1 1
H H9B 0.1645 0.2068 0.1265 0.069 Uiso calc R 1 1
C C14 0.6862(5) 0.0914(2) 0.28759(17) 0.0619(7) Uani d . 1 1
H H14 0.8350 0.0565 0.2626 0.074 Uiso calc R 1 1
C C13 0.5705(5) 0.1904(2) 0.24783(15) 0.0534(6) Uani d . 1 1
H H13 0.6362 0.2215 0.1959 0.064 Uiso calc R 1 1
C C3 0.1069(6) 0.2628(3) -0.21100(16) 0.0692(8) Uani d . 1 1
H H3 0.2295 0.3166 -0.2386 0.083 Uiso calc R 1 1
C C15 0.5848(5) 0.0436(2) 0.36365(17) 0.0646(7) Uani d . 1 1
H H15 0.6653 -0.0238 0.3886 0.078 Uiso calc R 1 1
C C6 -0.2639(5) 0.1006(3) -0.1276(2) 0.0709(8) Uani d . 1 1
H H6 -0.3871 0.0471 -0.1000 0.085 Uiso calc R 1 1
C C4 -0.0562(7) 0.1970(3) -0.25264(19) 0.0814(10) Uani d . 1 1
H H4 -0.0426 0.2064 -0.3094 0.098 Uiso calc R 1 1
C C20 -0.4465(6) 0.3326(4) 0.55469(18) 0.0879(10) Uani d . 1 1
H H20A -0.6216 0.3576 0.5500 0.105 Uiso calc R 1 1
H H20B -0.4458 0.2490 0.5814 0.105 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
C4 C5 C6 121.8(3)
C4 C5 H5 119.1
C6 C5 H5 119.1
C20 C21 H21B 109.5
C20 C21 H21A 109.5
H21B C21 H21A 109.5
C20 C21 H21C 109.5
H21B C21 H21C 109.5
H21A C21 H21C 109.5
C18 N2 C12 111.02(18)
C18 N2 C11 121.51(19)
C12 N2 C11 126.41(19)
C19 N3 C17 122.5(2)
C19 N3 C18 127.8(2)
C17 N3 C18 109.47(18)
C8 N1 C1 111.4(2)
C8 N1 C9 125.0(2)
C1 N1 C9 123.5(2)
C13 C12 C17 121.4(2)
C13 C12 N2 130.5(2)
C17 C12 N2 108.1(2)
C7 C2 C3 121.3(3)
C7 C2 C1 108.5(2)
C3 C2 C1 130.2(3)
C16 C17 C12 120.9(2)
C16 C17 N3 132.8(2)
C12 C17 N3 106.32(19)
C9 C10 C11 112.89(19)
C9 C10 H10A 109.0
C11 C10 H10A 109.0
C9 C10 H10B 109.0
C11 C10 H10B 109.0
H10A C10 H10B 107.8
C2 C7 C6 121.6(3)
C2 C7 C8 107.9(2)
C6 C7 C8 130.5(3)
C19 O5 C20 115.4(2)
O2 C8 N1 124.7(2)
O2 C8 C7 129.2(2)
N1 C8 C7 106.2(2)
O3 C18 N2 126.6(2)
O3 C18 N3 128.4(2)
N2 C18 N3 105.1(2)
O1 C1 N1 123.6(2)
O1 C1 C2 130.4(2)
N1 C1 C2 106.0(2)
N2 C11 C10 114.17(19)
N2 C11 H11A 108.7
C10 C11 H11A 108.7
N2 C11 H11B 108.7
C10 C11 H11B 108.7
H11A C11 H11B 107.6
C17 C16 C15 117.4(2)
C17 C16 H16 121.3
C15 C16 H16 121.3
O4 C19 O5 125.7(3)
O4 C19 N3 122.5(3)
O5 C19 N3 111.7(2)
N1 C9 C10 113.48(19)
N1 C9 H9A 108.9
C10 C9 H9A 108.9
N1 C9 H9B 108.9
C10 C9 H9B 108.9
H9A C9 H9B 107.7
C15 C14 C13 121.0(3)
C15 C14 H14 119.5
C13 C14 H14 119.5
C12 C13 C14 117.6(2)
C12 C13 H13 121.2
C14 C13 H13 121.2
C2 C3 C4 117.4(3)
C2 C3 H3 121.3
C4 C3 H3 121.3
C14 C15 C16 121.6(2)
C14 C15 H15 119.2
C16 C15 H15 119.2
C7 C6 C5 116.9(3)
C7 C6 H6 121.5
C5 C6 H6 121.5
C5 C4 C3 121.1(3)
C5 C4 H4 119.4
C3 C4 H4 119.4
C21 C20 O5 106.3(3)
C21 C20 H20A 110.5
O5 C20 H20A 110.5
C21 C20 H20B 110.5
O5 C20 H20B 110.5
H20A C20 H20B 108.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 C4 1.365(5)
C5 C6 1.383(4)
C5 H5 0.9300
C21 C20 1.452(4)
C21 H21B 0.9600
C21 H21A 0.9600
C21 H21C 0.9600
N2 C18 1.373(3)
N2 C12 1.394(3)
N2 C11 1.458(3)
N3 C19 1.397(3)
N3 C17 1.415(3)
N3 C18 1.426(3)
N1 C8 1.391(3)
N1 C1 1.394(3)
N1 C9 1.456(3)
C12 C13 1.374(3)
C12 C17 1.390(3)
C2 C7 1.374(3)
C2 C3 1.376(3)
C2 C1 1.478(3)
O3 C18 1.209(3)
C17 C16 1.381(3)
C10 C9 1.514(3)
C10 C11 1.517(3)
C10 H10A 0.9700
C10 H10B 0.9700
C7 C6 1.377(4)
C7 C8 1.484(3)
O5 C19 1.324(3)
O5 C20 1.493(3)
O4 C19 1.193(3)
C8 O2 1.208(3)
C1 O1 1.209(3)
C11 H11A 0.9700
C11 H11B 0.9700
C16 C15 1.383(4)
C16 H16 0.9300
C9 H9A 0.9700
C9 H9B 0.9700
C14 C15 1.377(4)
C14 C13 1.383(3)
C14 H14 0.9300
C13 H13 0.9300
C3 C4 1.384(4)
C3 H3 0.9300
C15 H15 0.9300
C6 H6 0.9300
C4 H4 0.9300
C20 H20A 0.9700
C20 H20B 0.9700
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
C9 H9A O2 1_655 0.97 2.72 3.523(3) 141
C13 H13 O2 1_655 0.93 2.67 3.375(3) 133
C21 H21B O3 2_466 0.96 2.67 3.261(4) 121
C11 H11A O1 2_665 0.97 2.68 3.201(3) 114
C5 H5 Cg1 2_555 0.93 2.91 3.750(3) 151
