##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1056943'
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2015-03-27
_journal_date_accepted     2015-03-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue      5
_journal_page_first     o297
_journal_page_last     o298
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2056989015006465
_journal_coeditor_code     HB7393
_publ_contact_author_name     'Mostafa Khouili'
_publ_contact_author_address
;
Laboratoire de Chimie Organique et Analytique,
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco
;
_publ_contact_author_email     'm.khouili@usms.ma'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;
Crystal stucture of methyl
2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Yassine, Hasna'
;
Laboratoire de Chimie Organique et Analytique,
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco
;
    'Khouili, Mostafa'
;
Laboratoire de Chimie Organique et Analytique,
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculté des Sciences, Université Mohammed V
Avenue Ibn Battouta, BP. 1014, Rabat, Morocco
;
    'Ketatni, El Mostafa'
;
Laboratoire de Spectrochimie Applique et Environnement,
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, BP 523, 23000 Béni-Mellal, Morocco
;
_chemical_name_systematic
;
Methyl 2-({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)benzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H16 N2 O5'
_chemical_formula_sum     'C17 H16 N2 O5'
_chemical_formula_iupac     'C17 H16 N2 O5'
_chemical_formula_weight     328.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c '
_symmetry_space_group_name_Hall     '-P 2ybc '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     9.005(8)
_cell_length_b     23.80(2)
_cell_length_c     7.400(7)
_cell_angle_alpha     90.00
_cell_angle_beta     93.66(4)
_cell_angle_gamma     90.00
_cell_volume     1583(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3364
_cell_measurement_theta_min     2.42
_cell_measurement_theta_max     26.73
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.42
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.29
_exptl_crystal_density_diffrn     1.378
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.103
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_absorpt_correction_T_min     0.6934
_exptl_absorpt_correction_T_max     0.7466
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     11500
_diffrn_reflns_av_R_equivalents     0.0657
_diffrn_reflns_av_sigmaI/netI     0.0736
_diffrn_reflns_theta_min     2.42
_diffrn_reflns_theta_max     26.73
_diffrn_reflns_theta_full     26.73
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -29
_diffrn_reflns_limit_k_max     30
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_refine_special_details
;
Refinement of F² against all reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on all data will be
even larger.
;
_reflns_number_total     3364
_reflns_number_gt     1667
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1218
_refine_ls_R_factor_gt     0.0502
_refine_ls_wR_factor_gt     0.1076
_refine_ls_wR_factor_ref     0.1373
_refine_ls_goodness_of_fit_ref     0.949
_refine_ls_restrained_S_all     0.949
_refine_ls_number_reflns     3364
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.212
_refine_diff_density_min     -0.200
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_extinction_coef     0.0052(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.8216(3) 0.50547(11) 0.6105(4) 0.0617(8) Uani d . 1 1 . .
    H H1A 0.8796 0.5351 0.5624 0.093 Uiso calc R 1 1 . .
    H H1B 0.8023 0.4772 0.5194 0.093 Uiso calc R 1 1 . .
    H H1C 0.8755 0.4891 0.7136 0.093 Uiso calc R 1 1 . .
    C C2 0.5813(3) 0.49037(10) 0.7155(3) 0.0413(6) Uani d . 1 1 . .
    C C3 0.4424(2) 0.51598(9) 0.7748(3) 0.0370(6) Uani d . 1 1 . .
    C C4 0.4261(3) 0.57446(9) 0.7763(3) 0.0463(6) Uani d . 1 1 . .
    H H4 0.5028 0.5968 0.7377 0.056 Uiso calc R 1 1 . .
    C C5 0.3000(3) 0.59993(10) 0.8334(3) 0.0524(7) Uani d . 1 1 . .
    H H5 0.2913 0.6389 0.8324 0.063 Uiso calc R 1 1 . .
    C C6 0.1861(3) 0.56676(10) 0.8925(3) 0.0496(7) Uani d . 1 1 . .
    H H6 0.1012 0.5837 0.9328 0.060 Uiso calc R 1 1 . .
    C C7 0.1975(3) 0.50878(9) 0.8921(3) 0.0421(6) Uani d . 1 1 . .
    H H7 0.1199 0.4871 0.9315 0.050 Uiso calc R 1 1 . .
    C C8 0.3249(3) 0.48226(9) 0.8331(3) 0.0377(6) Uani d . 1 1 . .
    C C9 0.2326(3) 0.38375(10) 0.8583(3) 0.0429(6) Uani d . 1 1 . .
    C C10 0.2281(3) 0.27870(9) 0.8808(3) 0.0420(6) Uani d . 1 1 . .
    C C11 0.0793(3) 0.27180(10) 0.8152(3) 0.0519(7) Uani d . 1 1 . .
    H H11 0.0219 0.3031 0.7827 0.062 Uiso calc R 1 1 . .
    C C12 0.0181(3) 0.21894(11) 0.7988(4) 0.0607(8) Uani d . 1 1 . .
    H H12 -0.0800 0.2150 0.7535 0.073 Uiso calc R 1 1 . .
    C C13 0.0991(3) 0.17166(11) 0.8482(4) 0.0627(8) Uani d . 1 1 . .
    H H13 0.0560 0.1362 0.8371 0.075 Uiso calc R 1 1 . .
    C C14 0.2450(3) 0.17759(10) 0.9142(3) 0.0511(7) Uani d . 1 1 . .
    H H14 0.2997 0.1457 0.9478 0.061 Uiso calc R 1 1 . .
    C C15 0.3129(3) 0.23038(9) 0.9319(3) 0.0407(6) Uani d . 1 1 . .
    C C16 0.4711(3) 0.23461(10) 1.0022(3) 0.0460(6) Uani d . 1 1 . .
    C C17 0.6894(3) 0.18555(11) 1.1114(4) 0.0695(9) Uani d . 1 1 . .
    H H17A 0.6980 0.2026 1.2292 0.104 Uiso calc R 1 1 . .
    H H17B 0.7470 0.2066 1.0300 0.104 Uiso calc R 1 1 . .
    H H17C 0.7258 0.1477 1.1196 0.104 Uiso calc R 1 1 . .
    N N2 0.2964(2) 0.33173(7) 0.8915(3) 0.0472(5) Uani d . 1 1 . .
    H H2N 0.3903 0.3306 0.9209 0.057 Uiso d R 1 1 . .
    N N3 0.3414(2) 0.42374(7) 0.8385(3) 0.0443(5) Uani d . 1 1 . .
    H H3N 0.4311 0.4140 0.8169 0.053 Uiso d R 1 1 . .
    O O1 0.68143(18) 0.52810(7) 0.6650(2) 0.0536(5) Uani d . 1 1 . .
    O O2 0.60738(18) 0.44002(7) 0.7108(2) 0.0557(5) Uani d . 1 1 . .
    O O3 0.0994(2) 0.39320(7) 0.8476(3) 0.0692(6) Uani d . 1 1 . .
    O O4 0.5330(2) 0.18523(7) 1.0436(3) 0.0618(5) Uani d . 1 1 . .
    O O5 0.5419(2) 0.27802(7) 1.0207(3) 0.0710(6) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C1 O1 . 1.453(3) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 O2 . 1.222(3) ?
    C2 O1 . 1.342(3) ?
    C2 C3 . 1.483(3) ?
    C3 C4 . 1.400(3) ?
    C3 C8 . 1.417(3) ?
    C4 C5 . 1.378(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.387(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.384(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.403(3) ?
    C7 H7 . 0.9300 ?
    C8 N3 . 1.401(3) ?
    C9 O3 . 1.218(3) ?
    C9 N2 . 1.381(3) ?
    C9 N3 . 1.381(3) ?
    C10 N2 . 1.404(3) ?
    C10 C11 . 1.405(4) ?
    C10 C15 . 1.418(3) ?
    C11 C12 . 1.376(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.377(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.379(4) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.400(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.489(4) ?
    C16 O5 . 1.217(3) ?
    C16 O4 . 1.328(3) ?
    C17 O4 . 1.465(3) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    N2 H2N . 0.8600 ?
    N3 H3N . 0.8646 ?
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
    O1 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    O1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O2 C2 O1 . . 121.0(2) ?
    O2 C2 C3 . . 125.3(2) ?
    O1 C2 C3 . . 113.7(2) ?
    C4 C3 C8 . . 118.7(2) ?
    C4 C3 C2 . . 120.1(2) ?
    C8 C3 C2 . . 121.2(2) ?
    C5 C4 C3 . . 121.9(2) ?
    C5 C4 H4 . . 119.0 ?
    C3 C4 H4 . . 119.0 ?
    C4 C5 C6 . . 119.1(2) ?
    C4 C5 H5 . . 120.4 ?
    C6 C5 H5 . . 120.4 ?
    C7 C6 C5 . . 120.7(2) ?
    C7 C6 H6 . . 119.6 ?
    C5 C6 H6 . . 119.6 ?
    C6 C7 C8 . . 120.8(2) ?
    C6 C7 H7 . . 119.6 ?
    C8 C7 H7 . . 119.6 ?
    N3 C8 C7 . . 121.7(2) ?
    N3 C8 C3 . . 119.4(2) ?
    C7 C8 C3 . . 118.7(2) ?
    O3 C9 N2 . . 125.1(2) ?
    O3 C9 N3 . . 124.7(2) ?
    N2 C9 N3 . . 110.3(2) ?
    N2 C10 C11 . . 122.0(2) ?
    N2 C10 C15 . . 119.2(2) ?
    C11 C10 C15 . . 118.8(2) ?
    C12 C11 C10 . . 120.3(2) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C11 C12 C13 . . 121.4(3) ?
    C11 C12 H12 . . 119.3 ?
    C13 C12 H12 . . 119.3 ?
    C12 C13 C14 . . 119.1(2) ?
    C12 C13 H13 . . 120.5 ?
    C14 C13 H13 . . 120.5 ?
    C13 C14 C15 . . 121.7(2) ?
    C13 C14 H14 . . 119.2 ?
    C15 C14 H14 . . 119.2 ?
    C14 C15 C10 . . 118.6(2) ?
    C14 C15 C16 . . 119.7(2) ?
    C10 C15 C16 . . 121.7(2) ?
    O5 C16 O4 . . 121.1(3) ?
    O5 C16 C15 . . 125.4(2) ?
    O4 C16 C15 . . 113.5(2) ?
    O4 C17 H17A . . 109.5 ?
    O4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C9 N2 C10 . . 128.3(2) ?
    C9 N2 H2N . . 117.6 ?
    C10 N2 H2N . . 114.0 ?
    C9 N3 C8 . . 127.8(2) ?
    C9 N3 H3N . . 120.8 ?
    C8 N3 H3N . . 111.1 ?
    C2 O1 C1 . . 116.1(2) ?
    C16 O4 C17 . . 117.03(19) ?
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
    O2 C2 C3 C4 . . . . 179.2(2) ?
    O1 C2 C3 C4 . . . . -0.7(3) ?
    O2 C2 C3 C8 . . . . 0.1(3) ?
    O1 C2 C3 C8 . . . . -179.83(19) ?
    C8 C3 C4 C5 . . . . 0.3(3) ?
    C2 C3 C4 C5 . . . . -178.9(2) ?
    C3 C4 C5 C6 . . . . 0.5(4) ?
    C4 C5 C6 C7 . . . . -0.9(4) ?
    C5 C6 C7 C8 . . . . 0.4(3) ?
    C6 C7 C8 N3 . . . . 177.4(2) ?
    C6 C7 C8 C3 . . . . 0.4(3) ?
    C4 C3 C8 N3 . . . . -177.8(2) ?
    C2 C3 C8 N3 . . . . 1.4(3) ?
    C4 C3 C8 C7 . . . . -0.8(3) ?
    C2 C3 C8 C7 . . . . 178.4(2) ?
    N2 C10 C11 C12 . . . . 177.0(2) ?
    C15 C10 C11 C12 . . . . -0.9(4) ?
    C10 C11 C12 C13 . . . . 1.0(4) ?
    C11 C12 C13 C14 . . . . -0.5(4) ?
    C12 C13 C14 C15 . . . . -0.2(4) ?
    C13 C14 C15 C10 . . . . 0.2(4) ?
    C13 C14 C15 C16 . . . . -179.4(2) ?
    N2 C10 C15 C14 . . . . -177.6(2) ?
    C11 C10 C15 C14 . . . . 0.3(3) ?
    N2 C10 C15 C16 . . . . 2.0(3) ?
    C11 C10 C15 C16 . . . . 179.9(2) ?
    C14 C15 C16 O5 . . . . 178.9(2) ?
    C10 C15 C16 O5 . . . . -0.8(4) ?
    C14 C15 C16 O4 . . . . -0.5(3) ?
    C10 C15 C16 O4 . . . . 179.9(2) ?
    O3 C9 N2 C10 . . . . 15.1(4) ?
    N3 C9 N2 C10 . . . . -164.8(2) ?
    C11 C10 N2 C9 . . . . 6.1(4) ?
    C15 C10 N2 C9 . . . . -176.1(2) ?
    O3 C9 N3 C8 . . . . 11.5(4) ?
    N2 C9 N3 C8 . . . . -168.6(2) ?
    C7 C8 N3 C9 . . . . 16.1(3) ?
    C3 C8 N3 C9 . . . . -167.0(2) ?
    O2 C2 O1 C1 . . . . -1.7(3) ?
    C3 C2 O1 C1 . . . . 178.3(2) ?
    O5 C16 O4 C17 . . . . -0.2(4) ?
    C15 C16 O4 C17 . . . . 179.1(2) ?
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
    N2 H2N O5 . 0.86 1.96 2.677(3) 140
    N3 H3N O2 . 0.86 1.92 2.659(3) 144
    C6 H6 O3 3_567 0.93 2.57 3.442(4) 157
    C17 H17C O2 4_566 0.96 2.46 3.176(4) 132
