#------------------------------------------------------------------------------
#$Date: 2016-02-06 09:14:56 +0200 (Sat, 06 Feb 2016) $
#$Revision: 176245 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/41/7224160.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_7224160
loop_
_publ_author_name
'Gholivand, Khodayar'
'Ebrahimi valmoozi, Ali Asghar'
'asadi, lida'
'hodaie, merat'
'sharifi, mahboobeh'
'Mazruee Kashani, hadi'
'Mahzouni, Hamid R.'
'Ghadamyari, Mohammad'
'kalateh, Ali Asghar'
'davari, ehsan'
'salehi, sami'
'Bonsaii, Mahyar'
_publ_section_title
;
 Phosphorhydrazides inhibitors: toxicological profile and antimicrobial
 evaluation assay, molecular modeling and QSAR study
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA24209F
_journal_year                    2016
_chemical_formula_moiety         'C17 H15 N2 O3 P'
_chemical_formula_sum            'C17 H15 N2 O3 P'
_chemical_formula_weight         326.28
_chemical_name_systematic
;
?
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-03-16 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                78.414(2)
_cell_angle_beta                 83.899(3)
_cell_angle_gamma                73.626(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2009(8)
_cell_length_b                   8.7089(8)
_cell_length_c                   11.2790(11)
_cell_measurement_reflns_used    2365
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     756.08(13)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega 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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            8362
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                3052
_reflns_number_total             3992
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c5ra24209f1.cif
_cod_data_source_block           214LR
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7224160
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.25560(4) 0.91445(4) 0.36132(3) 0.01747(11) Uani 1 1 d .
O1 O 0.15801(12) 0.81532(12) 0.44682(9) 0.0216(2) Uani 1 1 d .
O3 O 0.14738(15) 1.38238(13) 0.18947(11) 0.0303(3) Uani 1 1 d .
O4 O -0.27863(14) 1.35725(14) 0.26765(10) 0.0292(3) Uani 1 1 d .
N1 N 0.21170(15) 1.11200(14) 0.36316(11) 0.0204(3) Uani 1 1 d .
H1N H 0.2545 1.1469 0.4258 0.059(7) Uiso 1 1 d R
N2 N 0.04545(15) 1.20349(15) 0.33420(11) 0.0219(3) Uani 1 1 d .
H2N H -0.0372 1.1955 0.3923 0.026 Uiso 1 1 d R
C1 C 0.02863(19) 1.33603(17) 0.24449(13) 0.0223(3) Uani 1 1 d .
C2 C -0.14824(19) 1.42002(18) 0.21186(14) 0.0240(3) Uani 1 1 d .
C3 C -0.2081(2) 1.5508(2) 0.12620(16) 0.0306(4) Uani 1 1 d .
H3A H -0.1432 1.6149 0.0748 0.037 Uiso 1 1 calc R
C4 C -0.3859(2) 1.5743(2) 0.12746(16) 0.0361(4) Uani 1 1 d .
H4A H -0.4638 1.6576 0.0776 0.043 Uiso 1 1 calc R
C5 C -0.4234(2) 1.4554(2) 0.21328(16) 0.0340(4) Uani 1 1 d .
H5A H -0.5344 1.4413 0.2334 0.041 Uiso 1 1 calc R
C6 C 0.23149(17) 0.90464(17) 0.20674(13) 0.0178(3) Uani 1 1 d .
C7 C 0.27264(19) 1.01837(18) 0.11015(13) 0.0214(3) Uani 1 1 d .
H7A H 0.3073 1.1076 0.1255 0.026 Uiso 1 1 calc R
C8 C 0.2626(2) 1.00027(19) -0.00810(14) 0.0251(3) Uani 1 1 d .
H8A H 0.2897 1.0778 -0.0738 0.030 Uiso 1 1 calc R
C9 C 0.2132(2) 0.86947(19) -0.03088(14) 0.0261(3) Uani 1 1 d .
H9A H 0.2065 0.8579 -0.1121 0.031 Uiso 1 1 calc R
C10 C 0.17380(19) 0.75598(19) 0.06412(14) 0.0253(3) Uani 1 1 d .
H10A H 0.1404 0.6664 0.0482 0.030 Uiso 1 1 calc R
C11 C 0.18304(18) 0.77295(17) 0.18289(13) 0.0211(3) Uani 1 1 d .
H11A H 0.1563 0.6947 0.2481 0.025 Uiso 1 1 calc R
C12 C 0.47855(17) 0.84667(17) 0.38691(12) 0.0179(3) Uani 1 1 d .
C13 C 0.59571(19) 0.93110(18) 0.32904(13) 0.0223(3) Uani 1 1 d .
H13A H 0.5569 1.0362 0.2814 0.027 Uiso 1 1 calc R
C14 C 0.76883(19) 0.8607(2) 0.34149(14) 0.0252(3) Uani 1 1 d .
H14A H 0.8483 0.9186 0.3034 0.030 Uiso 1 1 calc R
C15 C 0.82622(18) 0.70585(19) 0.40937(14) 0.0237(3) Uani 1 1 d .
H15A H 0.9449 0.6568 0.4151 0.028 Uiso 1 1 calc R
C16 C 0.71152(19) 0.62296(18) 0.46848(15) 0.0250(3) Uani 1 1 d .
H16A H 0.7509 0.5178 0.5159 0.030 Uiso 1 1 calc R
C17 C 0.53722(19) 0.69463(18) 0.45805(14) 0.0227(3) Uani 1 1 d .
H17A H 0.4581 0.6388 0.5001 0.027 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'
P P 0.1023 0.0942 '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
O1 P1 N1 118.78(6)
O1 P1 C12 111.80(6)
N1 P1 C12 102.25(6)
O1 P1 C6 111.27(6)
N1 P1 C6 104.28(6)
C12 P1 C6 107.51(6)
C2 O4 C5 105.60(13)
N2 N1 P1 115.72(9)
N2 N1 H1N 113.1
P1 N1 H1N 119.0
C1 N2 N1 117.33(12)
C1 N2 H2N 121.5
N1 N2 H2N 116.7
O3 C1 N2 124.51(14)
O3 C1 C2 120.57(14)
N2 C1 C2 114.86(13)
C3 C2 O4 110.46(14)
C3 C2 C1 129.86(15)
O4 C2 C1 119.54(13)
C2 C3 C4 106.80(15)
C2 C3 H3A 126.6
C4 C3 H3A 126.6
C5 C4 C3 106.61(15)
C5 C4 H4A 126.7
C3 C4 H4A 126.7
C4 C5 O4 110.54(15)
C4 C5 H5A 124.7
O4 C5 H5A 124.7
C11 C6 C7 119.54(13)
C11 C6 P1 118.69(11)
C7 C6 P1 121.58(11)
C8 C7 C6 119.70(14)
C8 C7 H7A 120.2
C6 C7 H7A 120.2
C9 C8 C7 120.33(14)
C9 C8 H8A 119.8
C7 C8 H8A 119.8
C10 C9 C8 120.25(14)
C10 C9 H9A 119.9
C8 C9 H9A 119.9
C9 C10 C11 119.95(14)
C9 C10 H10A 120.0
C11 C10 H10A 120.0
C10 C11 C6 120.23(14)
C10 C11 H11A 119.9
C6 C11 H11A 119.9
C17 C12 C13 119.37(13)
C17 C12 P1 117.02(11)
C13 C12 P1 123.25(11)
C14 C13 C12 119.79(13)
C14 C13 H13A 120.1
C12 C13 H13A 120.1
C15 C14 C13 120.26(14)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C16 C15 C14 120.31(14)
C16 C15 H15A 119.8
C14 C15 H15A 119.8
C15 C16 C17 119.59(14)
C15 C16 H16A 120.2
C17 C16 H16A 120.2
C12 C17 C16 120.61(14)
C12 C17 H17A 119.7
C16 C17 H17A 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4855(10)
P1 N1 1.6594(12)
P1 C12 1.7916(14)
P1 C6 1.7969(14)
O3 C1 1.2202(18)
O4 C2 1.3735(18)
O4 C5 1.374(2)
N1 N2 1.4065(16)
N1 H1N 0.9552
N2 C1 1.3587(19)
N2 H2N 0.8980
C1 C2 1.477(2)
C2 C3 1.347(2)
C3 C4 1.413(2)
C3 H3A 0.9500
C4 C5 1.348(3)
C4 H4A 0.9500
C5 H5A 0.9500
C6 C11 1.396(2)
C6 C7 1.399(2)
C7 C8 1.388(2)
C7 H7A 0.9500
C8 C9 1.388(2)
C8 H8A 0.9500
C9 C10 1.382(2)
C9 H9A 0.9500
C10 C11 1.389(2)
C10 H10A 0.9500
C11 H11A 0.9500
C12 C17 1.387(2)
C12 C13 1.4008(19)
C13 C14 1.389(2)
C13 H13A 0.9500
C14 C15 1.389(2)
C14 H14A 0.9500
C15 C16 1.381(2)
C15 H15A 0.9500
C16 C17 1.396(2)
C16 H16A 0.9500
C17 H17A 0.9500
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 O1 2_576 0.90 1.97 2.8332(16) 160
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
O1 P1 N1 N2 -61.95(12)
C12 P1 N1 N2 174.48(9)
C6 P1 N1 N2 62.58(11)
P1 N1 N2 C1 -126.56(12)
N1 N2 C1 O3 -1.5(2)
N1 N2 C1 C2 175.62(12)
C5 O4 C2 C3 -0.27(18)
C5 O4 C2 C1 -176.37(13)
O3 C1 C2 C3 -1.0(3)
N2 C1 C2 C3 -178.26(16)
O3 C1 C2 O4 174.25(13)
N2 C1 C2 O4 -3.0(2)
O4 C2 C3 C4 0.47(19)
C1 C2 C3 C4 176.05(15)
C2 C3 C4 C5 -0.5(2)
C3 C4 C5 O4 0.3(2)
C2 O4 C5 C4 -0.05(18)
O1 P1 C6 C11 -22.00(13)
N1 P1 C6 C11 -151.21(11)
C12 P1 C6 C11 100.74(12)
O1 P1 C6 C7 163.00(11)
N1 P1 C6 C7 33.79(13)
C12 P1 C6 C7 -74.26(13)
C11 C6 C7 C8 0.9(2)
P1 C6 C7 C8 175.83(11)
C6 C7 C8 C9 -0.5(2)
C7 C8 C9 C10 -0.1(2)
C8 C9 C10 C11 0.2(2)
C9 C10 C11 C6 0.2(2)
C7 C6 C11 C10 -0.8(2)
P1 C6 C11 C10 -175.86(11)
O1 P1 C12 C17 14.98(14)
N1 P1 C12 C17 143.11(11)
C6 P1 C12 C17 -107.43(12)
O1 P1 C12 C13 -171.89(11)
N1 P1 C12 C13 -43.76(13)
C6 P1 C12 C13 65.71(13)
C17 C12 C13 C14 1.3(2)
P1 C12 C13 C14 -171.72(11)
C12 C13 C14 C15 1.1(2)
C13 C14 C15 C16 -2.3(2)
C14 C15 C16 C17 1.0(2)
C13 C12 C17 C16 -2.5(2)
P1 C12 C17 C16 170.93(11)
C15 C16 C17 C12 1.3(2)
