#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229074.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_2229074
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Jasinski, Jerry P.'
'Butcher, Ray J.'
_publ_section_title
;
 Ethyl 2-(4-nitrobenzamido)benzoate, a non-merohedral twin
;
_journal_coeditor_code           HG2769
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o465
_journal_paper_doi               10.1107/S1600536811002236
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H14 N2 O5'
_chemical_formula_moiety         'C16 H14 N2 O5'
_chemical_formula_sum            'C16 H14 N2 O5'
_chemical_formula_weight         314.29
_chemical_name_systematic
;
Ethyl 2-(4-nitrobenzamido)benzoate
;
_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
_cell_angle_alpha                102.833(4)
_cell_angle_beta                 94.296(4)
_cell_angle_gamma                107.567(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9802(3)
_cell_length_b                   9.3570(4)
_cell_length_c                   12.5779(5)
_cell_measurement_reflns_used    4228
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      73.9181
_cell_measurement_theta_min      5.1205
_cell_volume                     754.68(6)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_sigmaI/netI    0.0082
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10410
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.45
_diffrn_reflns_theta_min         5.13
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         10410
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0526
_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)+(0.0935P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                9282
_reflns_number_total             10410
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2769.cif
_cod_data_source_block           I
_cod_database_code               2229074
_cod_database_fobs_code          2229074
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_disorder_assembly
_atom_site_disorder_group
O O1 -0.18667(13) 0.04273(9) 0.01289(7) 0.1014(3) Uani d . 1 . .
O O2 0.02489(16) 0.25940(11) 0.00650(7) 0.1088(3) Uani d . 1 . .
O O3 0.12371(18) 0.20254(8) 0.56742(8) 0.1132(3) Uani d . 1 . .
O O4 0.40086(11) 0.74605(7) 0.55727(5) 0.06973(19) Uani d . 1 . .
O O5 0.52758(10) 0.93554(6) 0.71099(5) 0.06630(18) Uani d . 1 . .
N N1 -0.05477(14) 0.16683(10) 0.05611(8) 0.0793(3) Uani d . 1 . .
N N2 0.24927(11) 0.45878(8) 0.57997(6) 0.06052(19) Uani d . 1 . .
H H2 0.2733 0.5241 0.5401 0.073 Uiso calc R 1 . .
C C1 0.11370(12) 0.27848(8) 0.40099(8) 0.0583(2) Uani d . 1 . .
C C2 0.01013(15) 0.12590(9) 0.34180(9) 0.0697(3) Uani d . 1 . .
H H2A -0.0232 0.0483 0.3789 0.084 Uiso calc R 1 . .
C C3 -0.04350(15) 0.08854(10) 0.22924(9) 0.0725(3) Uani d . 1 . .
H H3A -0.1131 -0.0134 0.1900 0.087 Uiso calc R 1 . .
C C4 0.00737(13) 0.20403(10) 0.17595(8) 0.0637(2) Uani d . 1 . .
C C5 0.11309(14) 0.35587(10) 0.23110(8) 0.0653(2) Uani d . 1 . .
H H5A 0.1488 0.4323 0.1930 0.078 Uiso calc R 1 . .
C C6 0.16450(14) 0.39178(9) 0.34375(8) 0.0634(2) Uani d . 1 . .
H H6A 0.2347 0.4940 0.3822 0.076 Uiso calc R 1 . .
C C7 0.16219(14) 0.30877(9) 0.52350(8) 0.0657(2) Uani d . 1 . .
C C8 0.30613(12) 0.52356(9) 0.69344(7) 0.0574(2) Uani d . 1 A .
C C9 0.26962(16) 0.43559(12) 0.77040(9) 0.0753(3) Uani d . 1 . .
H H9A 0.2068 0.3287 0.7464 0.090 Uiso calc R 1 . .
C C10 0.32558(18) 0.50539(14) 0.88137(10) 0.0870(3) Uani d . 1 . .
H H10A 0.2980 0.4450 0.9315 0.104 Uiso calc R 1 . .
C C11 0.42132(18) 0.66243(14) 0.91963(9) 0.0817(3) Uani d . 1 . .
H H11A 0.4610 0.7079 0.9949 0.098 Uiso calc R 1 . .
C C12 0.45786(14) 0.75151(11) 0.84562(8) 0.0656(2) Uani d . 1 A .
H H12A 0.5215 0.8581 0.8714 0.079 Uiso calc R 1 . .
C C13 0.40165(12) 0.68549(9) 0.73274(7) 0.0541(2) Uani d . 1 . .
C C14 0.44109(12) 0.78829(9) 0.65684(7) 0.0544(2) Uani d . 1 A .
C C15A 0.5896(13) 1.0482(9) 0.6489(8) 0.0698(11) Uani d PDU 0.643(14) A 1
H H15A 0.4716 1.0511 0.6046 0.084 Uiso calc PR 0.643(14) A 1
H H15B 0.6805 1.0202 0.5997 0.084 Uiso calc PR 0.643(14) A 1
C C16A 0.6954(13) 1.2037(5) 0.7264(5) 0.0928(12) Uani d PDU 0.643(14) A 1
H H16A 0.7493 1.2776 0.6850 0.139 Uiso calc PR 0.643(14) A 1
H H16B 0.8043 1.1978 0.7747 0.139 Uiso calc PR 0.643(14) A 1
H H16C 0.6005 1.2359 0.7693 0.139 Uiso calc PR 0.643(14) A 1
C C15B 0.550(2) 1.0505(18) 0.6437(16) 0.0698(11) Uani d PDU 0.357(14) A 2
H H15C 0.6508 1.0448 0.5953 0.084 Uiso calc PR 0.357(14) A 2
H H15D 0.4216 1.0358 0.6001 0.084 Uiso calc PR 0.357(14) A 2
C C16B 0.6185(17) 1.1998(11) 0.7309(9) 0.0928(12) Uani d PDU 0.357(14) A 2
H H16D 0.6536 1.2847 0.6970 0.139 Uiso calc PR 0.357(14) A 2
H H16E 0.7352 1.2045 0.7788 0.139 Uiso calc PR 0.357(14) A 2
H H16F 0.5108 1.2062 0.7729 0.139 Uiso calc PR 0.357(14) A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O5 C15A . . 118.5(3) ?
C14 O5 C15B . . 116.1(5) ?
O2 N1 O1 . . 123.88(10) ?
O2 N1 C4 . . 118.86(8) ?
O1 N1 C4 . . 117.26(10) ?
C7 N2 C8 . . 129.57(7) ?
C7 N2 H2 . . 115.2 ?
C8 N2 H2 . . 115.2 ?
C6 C1 C2 . . 118.55(9) ?
C6 C1 C7 . . 124.29(7) ?
C2 C1 C7 . . 117.16(8) ?
C3 C2 C1 . . 120.87(9) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C4 C3 C2 . . 118.78(8) ?
C4 C3 H3A . . 120.6 ?
C2 C3 H3A . . 120.6 ?
C3 C4 C5 . . 122.19(9) ?
C3 C4 N1 . . 119.44(8) ?
C5 C4 N1 . . 118.36(9) ?
C6 C5 C4 . . 118.41(8) ?
C6 C5 H5A . . 120.8 ?
C4 C5 H5A . . 120.8 ?
C5 C6 C1 . . 121.18(8) ?
C5 C6 H6A . . 119.4 ?
C1 C6 H6A . . 119.4 ?
O3 C7 N2 . . 123.20(9) ?
O3 C7 C1 . . 120.67(8) ?
N2 C7 C1 . . 116.13(7) ?
C9 C8 N2 . . 122.86(8) ?
C9 C8 C13 . . 118.22(8) ?
N2 C8 C13 . . 118.91(7) ?
C10 C9 C8 . . 120.58(9) ?
C10 C9 H9A . . 119.7 ?
C8 C9 H9A . . 119.7 ?
C11 C10 C9 . . 121.27(9) ?
C11 C10 H10A . . 119.4 ?
C9 C10 H10A . . 119.4 ?
C12 C11 C10 . . 119.23(10) ?
C12 C11 H11A . . 120.4 ?
C10 C11 H11A . . 120.4 ?
C11 C12 C13 . . 121.24(9) ?
C11 C12 H12A . . 119.4 ?
C13 C12 H12A . . 119.4 ?
C12 C13 C8 . . 119.45(8) ?
C12 C13 C14 . . 118.76(8) ?
C8 C13 C14 . . 121.78(7) ?
O4 C14 O5 . . 122.72(7) ?
O4 C14 C13 . . 125.49(7) ?
O5 C14 C13 . . 111.79(7) ?
O5 C15A C16A . . 109.2(7) ?
O5 C15A H15A . . 109.8 ?
C16A C15A H15A . . 109.8 ?
O5 C15A H15B . . 109.8 ?
C16A C15A H15B . . 109.8 ?
H15A C15A H15B . . 108.3 ?
C16B C15B O5 . . 101.6(13) ?
C16B C15B H15C . . 111.4 ?
O5 C15B H15C . . 111.4 ?
C16B C15B H15D . . 111.4 ?
O5 C15B H15D . . 111.4 ?
H15C C15B H15D . . 109.3 ?
C15B C16B H16D . . 109.5 ?
C15B C16B H16E . . 109.5 ?
H16D C16B H16E . . 109.5 ?
C15B C16B H16F . . 109.5 ?
H16D C16B H16F . . 109.5 ?
H16E C16B H16F . . 109.5 ?
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 N1 . 1.2210(11) ?
O2 N1 . 1.2042(12) ?
O3 C7 . 1.2126(11) ?
O4 C14 . 1.2099(10) ?
O5 C14 . 1.3214(10) ?
O5 C15A . 1.431(12) ?
O5 C15B . 1.49(2) ?
N1 C4 . 1.4694(13) ?
N2 C7 . 1.3497(11) ?
N2 C8 . 1.3955(12) ?
N2 H2 . 0.8600 ?
C1 C6 . 1.3851(12) ?
C1 C2 . 1.3926(12) ?
C1 C7 . 1.4963(13) ?
C2 C3 . 1.3742(15) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3670(14) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3773(12) ?
C5 C6 . 1.3743(14) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C8 C9 . 1.3943(13) ?
C8 C13 . 1.4116(12) ?
C9 C10 . 1.3735(16) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.3720(17) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.3705(14) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.3899(13) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.4833(12) ?
C15A C16A . 1.492(6) ?
C15A H15A . 0.9700 ?
C15A H15B . 0.9700 ?
C16A H16A . 0.9600 ?
C16A H16B . 0.9600 ?
C16A H16C . 0.9600 ?
C15B C16B . 1.490(12) ?
C15B H15C . 0.9700 ?
C15B H15D . 0.9700 ?
C16B H16D . 0.9600 ?
C16B H16E . 0.9600 ?
C16B H16F . 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
N2 H2 O4 . 0.86 1.95 2.6638(9) 139
C2 H2A O3 2_556 0.93 2.50 3.4069(11) 166
C10 H10A O2 1_556 0.93 2.56 3.3716(14) 146
C12 H12A O1 1_666 0.93 2.50 3.2554(12) 138
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
C6 C1 C2 C3 . . . . -1.00(14) ?
C7 C1 C2 C3 . . . . 178.82(9) ?
C1 C2 C3 C4 . . . . 0.25(15) ?
C2 C3 C4 C5 . . . . 1.01(15) ?
C2 C3 C4 N1 . . . . -177.99(8) ?
O2 N1 C4 C3 . . . . -164.54(10) ?
O1 N1 C4 C3 . . . . 15.94(13) ?
O2 N1 C4 C5 . . . . 16.42(14) ?
O1 N1 C4 C5 . . . . -163.10(9) ?
C3 C4 C5 C6 . . . . -1.46(15) ?
N1 C4 C5 C6 . . . . 177.55(8) ?
C4 C5 C6 C1 . . . . 0.66(14) ?
C2 C1 C6 C5 . . . . 0.53(14) ?
C7 C1 C6 C5 . . . . -179.27(8) ?
C8 N2 C7 O3 . . . . -1.98(17) ?
C8 N2 C7 C1 . . . . 177.96(8) ?
C6 C1 C7 O3 . . . . -175.60(10) ?
C2 C1 C7 O3 . . . . 4.60(15) ?
C6 C1 C7 N2 . . . . 4.46(14) ?
C2 C1 C7 N2 . . . . -175.34(8) ?
C7 N2 C8 C9 . . . . -3.14(15) ?
C7 N2 C8 C13 . . . . 178.00(8) ?
N2 C8 C9 C10 . . . . -178.89(10) ?
C13 C8 C9 C10 . . . . -0.03(15) ?
C8 C9 C10 C11 . . . . -1.01(18) ?
C9 C10 C11 C12 . . . . 1.36(18) ?
C10 C11 C12 C13 . . . . -0.66(17) ?
C11 C12 C13 C8 . . . . -0.36(14) ?
C11 C12 C13 C14 . . . . 178.66(9) ?
C9 C8 C13 C12 . . . . 0.70(13) ?
N2 C8 C13 C12 . . . . 179.60(8) ?
C9 C8 C13 C14 . . . . -178.29(8) ?
N2 C8 C13 C14 . . . . 0.62(12) ?
C15A O5 C14 O4 . . . . -4.7(4) ?
C15B O5 C14 O4 . . . . 7.5(7) ?
C15A O5 C14 C13 . . . . 175.3(4) ?
C15B O5 C14 C13 . . . . -172.6(7) ?
C12 C13 C14 O4 . . . . 179.61(8) ?
C8 C13 C14 O4 . . . . -1.39(14) ?
C12 C13 C14 O5 . . . . -0.37(11) ?
C8 C13 C14 O5 . . . . 178.63(7) ?
C14 O5 C15A C16A . . . . -176.2(3) ?
C15B O5 C15A C16A . . . . 104(5) ?
C14 O5 C15B C16B . . . . 171.2(6) ?
C15A O5 C15B C16B . . . . -83(4) ?
