#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023816
loop_
_publ_author_name
'Stefania Butini'
'Emanuele Gabellieri'
'Paul Brady Huleatt'
'Giuseppe Campiani'
'Silvia Franceschini'
'Margherita Brindisi'
'Sindu Ros'
'Salvatore Sanna Coccone'
'Isabella Fiorini'
'Ettore Novellino'
'Gianluca Giorgi'
'Sandra Gemma'
_publ_contact_author_address
; Dipartimento di Chimica,
  Università degli Studi di Siena
  Via Aldo Moro
  I-53100 Siena
  Italy
;
_publ_contact_author_email       gianluca.giorgi@unisi.it
_publ_contact_author_fax         '+39 0577 234241'
_publ_contact_author_name        'Gianluca Giorgi, Ph. D.'
_publ_contact_author_phone       '+39 0577 234233'
_publ_section_title
;
 An Efficient Approach to Chiral C8/C9-Piperazino-Substituted
 1,4-Benzodiazepin-2-ones as Peptidomimetic Scaffolds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8458
_journal_page_last               8468
_journal_paper_doi               10.1021/jo8015456
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H8 Cl N O4'
_chemical_formula_sum            'C13 H8 Cl N O4'
_chemical_formula_weight         277.65
_chemical_name_systematic
;
phenyl 4-chloro-2-nitrobenzoate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2110(8)
_cell_length_b                   11.8570(10)
_cell_length_c                   13.6090(12)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.4
_cell_measurement_theta_min      3.2
_cell_volume                     1263.8(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2680
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0264
_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)+(0.0270P)²+0.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                1878
_reflns_number_total             2018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8015456_si_002.cif
_cod_data_source_block           260405
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4023816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 1.04505(10) 0.98913(6) 0.54588(6) 0.0904(2) Uani 1 1 d . . .
C1 C 0.5417(2) 1.16628(14) 0.40549(13) 0.0520(4) Uani 1 1 d . . .
C2 C 0.6243(2) 1.10803(14) 0.34537(13) 0.0493(4) Uani 1 1 d . . .
N1 N 0.5410(2) 1.09731(14) 0.23384(12) 0.0615(4) Uani 1 1 d . . .
O1 O 0.6312(3) 1.06981(18) 0.18135(12) 0.1009(6) Uani 1 1 d . . .
O2 O 0.3890(2) 1.11442(15) 0.20046(11) 0.0840(5) Uani 1 1 d . . .
C3 C 0.7776(2) 1.05439(15) 0.38671(15) 0.0547(4) Uani 1 1 d . . .
H3 H 0.8304 1.0164 0.3448 0.066 Uiso 1 1 calc R . .
C4 C 0.8513(3) 1.05820(16) 0.49149(15) 0.0583(5) Uani 1 1 d . . .
C5 C 0.7753(3) 1.11385(18) 0.55435(15) 0.0673(6) Uani 1 1 d . . .
H5 H 0.8266 1.1154 0.6253 0.081 Uiso 1 1 calc R . .
C6 C 0.6218(3) 1.16737(18) 0.51075(15) 0.0661(6) Uani 1 1 d . . .
H6 H 0.5703 1.2055 0.5533 0.079 Uiso 1 1 calc R . .
C7 C 0.3853(3) 1.23611(17) 0.36213(14) 0.0565(5) Uani 1 1 d . . .
O3 O 0.37787(19) 1.31730(12) 0.30890(12) 0.0708(4) Uani 1 1 d . . .
O4 O 0.25886(19) 1.19943(12) 0.39764(12) 0.0716(4) Uani 1 1 d . . .
C8 C 0.1041(3) 1.26118(17) 0.36771(15) 0.0598(5) Uani 1 1 d . . .
C9 C 0.0015(3) 1.2593(2) 0.26836(18) 0.0766(6) Uani 1 1 d . . .
H9 H 0.0328 1.2190 0.2182 0.092 Uiso 1 1 calc R . .
C10 C -0.1502(3) 1.3187(2) 0.2438(2) 0.0857(7) Uani 1 1 d . . .
H10 H -0.2212 1.3195 0.1762 0.103 Uiso 1 1 calc R . .
C11 C -0.1967(3) 1.3764(2) 0.3186(2) 0.0816(7) Uani 1 1 d . . .
H11 H -0.2991 1.4161 0.3016 0.098 Uiso 1 1 calc R . .
C12 C -0.0927(3) 1.3755(2) 0.4178(2) 0.0738(6) Uani 1 1 d . . .
H12 H -0.1250 1.4140 0.4685 0.089 Uiso 1 1 calc R . .
C13 C 0.0600(3) 1.31786(18) 0.44337(17) 0.0646(5) Uani 1 1 d . . .
H13 H 0.1317 1.3175 0.5108 0.078 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.66(18) . . ?
C6 C1 C7 119.24(17) . . ?
C2 C1 C7 123.75(15) . . ?
C3 C2 C1 122.54(17) . . ?
C3 C2 N1 117.90(17) . . ?
C1 C2 N1 119.47(17) . . ?
O2 N1 O1 124.41(18) . . ?
O2 N1 C2 118.68(17) . . ?
O1 N1 C2 116.91(18) . . ?
C2 C3 C4 118.35(19) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.56(19) . . ?
C5 C4 Cl 119.31(15) . . ?
C3 C4 Cl 119.13(17) . . ?
C4 C5 C6 118.86(18) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 122.04(19) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O3 C7 O4 125.07(18) . . ?
O3 C7 C1 124.60(18) . . ?
O4 C7 C1 110.16(15) . . ?
C7 O4 C8 116.96(14) . . ?
C9 C8 C13 122.1(2) . . ?
C9 C8 O4 120.7(2) . . ?
C13 C8 O4 117.10(18) . . ?
C8 C9 C10 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.7(2) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C4 1.744(2) . ?
C1 C6 1.385(3) . ?
C1 C2 1.392(2) . ?
C1 C7 1.493(3) . ?
C2 C3 1.372(3) . ?
C2 N1 1.471(2) . ?
N1 O2 1.210(2) . ?
N1 O1 1.218(2) . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.195(2) . ?
C7 O4 1.343(2) . ?
O4 C8 1.416(2) . ?
C8 C9 1.362(3) . ?
C8 C13 1.366(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(3) . . . . ?
C7 C1 C2 C3 172.86(17) . . . . ?
C6 C1 C2 N1 176.09(18) . . . . ?
C7 C1 C2 N1 -10.7(3) . . . . ?
C3 C2 N1 O2 158.91(18) . . . . ?
C1 C2 N1 O2 -17.7(3) . . . . ?
C3 C2 N1 O1 -20.0(3) . . . . ?
C1 C2 N1 O1 163.39(19) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
N1 C2 C3 C4 -176.14(17) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 Cl 179.24(14) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
Cl C4 C5 C6 -179.52(16) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 -173.49(18) . . . . ?
C6 C1 C7 O3 111.6(2) . . . . ?
C2 C1 C7 O3 -61.5(3) . . . . ?
C6 C1 C7 O4 -64.0(2) . . . . ?
C2 C1 C7 O4 122.99(19) . . . . ?
O3 C7 O4 C8 1.2(3) . . . . ?
C1 C7 O4 C8 176.71(17) . . . . ?
C7 O4 C8 C9 69.4(3) . . . . ?
C7 O4 C8 C13 -113.3(2) . . . . ?
C13 C8 C9 C10 1.2(3) . . . . ?
O4 C8 C9 C10 178.4(2) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
O4 C8 C13 C12 -177.69(18) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
