#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/54/2105473.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_2105473
loop_
_publ_author_name
'Tarahhomi, Atekeh'
'Pourayoubi, Mehrdad'
'Golen, James A.'
'Zargaran, Poorya'
'Elahi, Behrouz'
'Rheingold, Arnold L.'
'Leyva Ramírez, Marco A.'
'Mancilla Percino, Teresa'
_publ_section_title
;
 Hirshfeld surface analysis of new phosphoramidates
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              260
_journal_page_last               270
_journal_paper_doi               10.1107/S2052519213009445
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C18 H15 Br1 N1 O3 P1'
_chemical_formula_sum            'C18 H15 Br N O3 P'
_chemical_formula_weight         404.19
_chemical_name_common            pzn10
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                108.3036(8)
_cell_angle_beta                 94.3109(10)
_cell_angle_gamma                118.0843(9)
_cell_formula_units_Z            2
_cell_length_a                   10.1842(2)
_cell_length_b                   10.2741(2)
_cell_length_c                   10.7121(3)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      1
_cell_volume                     904.95(4)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2001)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'WinGX (Farrugia, 1999); enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11476
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.79
_exptl_absorpt_coefficient_mu    2.374
_exptl_absorpt_correction_T_max  0.5460
_exptl_absorpt_correction_T_min  0.4283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.898
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.7366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                3259
_reflns_number_total             4019
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            so5063.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2105473
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 C1 1.1855(3) 0.7708(3) 0.7538(3) 0.0413(6) Uani d . 1 1
C C2 1.1072(4) 0.6164(4) 0.7455(4) 0.0661(9) Uani d . 1 1
H H2 1.0011 0.551 0.7068 0.079 Uiso calc R 1 1
C C3 1.1886(5) 0.5588(5) 0.7956(5) 0.0779(12) Uani d . 1 1
H H3 1.1372 0.4543 0.7913 0.093 Uiso calc R 1 1
C C4 1.3449(5) 0.6561(5) 0.8516(4) 0.0695(10) Uani d . 1 1
H H4 1.3991 0.6175 0.886 0.083 Uiso calc R 1 1
C C5 1.4220(4) 0.8095(5) 0.8576(4) 0.0695(10) Uani d . 1 1
H H5 1.5283 0.8744 0.8951 0.083 Uiso calc R 1 1
C C6 1.3416(4) 0.8688(4) 0.8075(3) 0.0565(8) Uani d . 1 1
H H6 1.3931 0.9727 0.8106 0.068 Uiso calc R 1 1
C C7 0.8986(3) 1.0471(3) 0.6995(3) 0.0394(6) Uani d . 1 1
C C8 0.8648(4) 1.0803(4) 0.5919(3) 0.0523(7) Uani d . 1 1
H H8 0.8919 1.0468 0.5121 0.063 Uiso calc R 1 1
C C9 0.7902(5) 1.1637(5) 0.6026(4) 0.0727(11) Uani d . 1 1
H H9 0.7665 1.1863 0.5295 0.087 Uiso calc R 1 1
C C10 0.7506(5) 1.2137(5) 0.7194(4) 0.0782(12) Uani d . 1 1
H H10 0.7012 1.2712 0.7262 0.094 Uiso calc R 1 1
C C11 0.7836(6) 1.1790(6) 0.8259(4) 0.0812(13) Uani d . 1 1
H H11 0.7557 1.2123 0.9053 0.097 Uiso calc R 1 1
C C12 0.8580(5) 1.0951(5) 0.8176(4) 0.0671(10) Uani d . 1 1
H H12 0.8803 1.0714 0.8905 0.081 Uiso calc R 1 1
C C13 0.7601(3) 0.6365(3) 0.7361(3) 0.0371(5) Uani d . 1 1
C C14 0.7427(3) 0.5713(4) 0.5969(3) 0.0478(7) Uani d . 1 1
H H14 0.8159 0.6283 0.5577 0.057 Uiso calc R 1 1
C C15 0.6151(4) 0.4201(4) 0.5164(3) 0.0565(8) Uani d . 1 1
H H15 0.6039 0.3766 0.4232 0.068 Uiso calc R 1 1
C C16 0.5052(4) 0.3336(4) 0.5718(3) 0.0541(8) Uani d . 1 1
H H16 0.4205 0.2323 0.5174 0.065 Uiso calc R 1 1
C C17 0.5239(3) 0.4012(3) 0.7105(3) 0.0440(6) Uani d . 1 1
C C18 0.6495(3) 0.5509(3) 0.7936(3) 0.0389(6) Uani d . 1 1
H H18 0.66 0.5938 0.8868 0.047 Uiso calc R 1 1
N N1 0.8881(2) 0.7876(3) 0.8259(2) 0.0389(5) Uani d D 1 1
O O1 1.1424(2) 1.0553(2) 0.91797(18) 0.0415(4) Uani d . 1 1
O O2 1.1029(2) 0.8281(2) 0.69854(18) 0.0398(4) Uani d . 1 1
O O3 0.9737(2) 0.9605(2) 0.67965(19) 0.0443(4) Uani d . 1 1
P P1 1.03410(7) 0.91819(7) 0.79212(7) 0.03352(16) Uani d . 1 1
Br Br1 0.37725(4) 0.28278(4) 0.79178(4) 0.06523(15) Uani d . 1 1
H H1 0.882(4) 0.829(4) 0.9082(13) 0.054(9) Uiso d D 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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 122.0(3)
C6 C1 O2 119.0(3)
C2 C1 O2 118.9(3)
C1 C2 C3 118.9(3)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 119.9(4)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 120.6(3)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.1(4)
C4 C5 H5 120
C6 C5 H5 120
C1 C6 C5 118.5(3)
C1 C6 H6 120.8
C5 C6 H6 120.8
C8 C7 C12 120.9(3)
C8 C7 O3 115.6(2)
C12 C7 O3 123.5(2)
C7 C8 C9 119.2(3)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.7(3)
C10 C9 H9 119.6
C8 C9 H9 119.6
C11 C10 C9 119.7(3)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 120.8(3)
C10 C11 H11 119.6
C12 C11 H11 119.6
C7 C12 C11 118.7(3)
C7 C12 H12 120.6
C11 C12 H12 120.6
C14 C13 C18 119.8(3)
C14 C13 N1 123.2(2)
C18 C13 N1 117.0(2)
C13 C14 C15 119.5(3)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 121.4(3)
C16 C15 H15 119.3
C14 C15 H15 119.3
C15 C16 C17 118.2(3)
C15 C16 H16 120.9
C17 C16 H16 120.9
C18 C17 C16 121.9(3)
C18 C17 Br1 118.5(2)
C16 C17 Br1 119.5(2)
C17 C18 C13 119.1(3)
C17 C18 H18 120.4
C13 C18 H18 120.4
C13 N1 P1 129.42(18)
C13 N1 H1 117(2)
P1 N1 H1 112(2)
C1 O2 P1 120.04(16)
C7 O3 P1 124.83(16)
O1 P1 O2 116.23(11)
O1 P1 O3 115.60(11)
O2 P1 O3 95.39(10)
O1 P1 N1 110.43(11)
O2 P1 N1 108.56(11)
O3 P1 N1 109.64(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.366(4)
C1 C2 1.368(4)
C1 O2 1.419(3)
C2 C3 1.385(5)
C2 H2 0.93
C3 C4 1.369(6)
C3 H3 0.93
C4 C5 1.367(6)
C4 H4 0.93
C5 C6 1.392(5)
C5 H5 0.93
C6 H6 0.93
C7 C8 1.364(4)
C7 C12 1.376(4)
C7 O3 1.404(3)
C8 C9 1.374(5)
C8 H8 0.93
C9 C10 1.363(5)
C9 H9 0.93
C10 C11 1.362(5)
C10 H10 0.93
C11 C12 1.378(5)
C11 H11 0.93
C12 H12 0.93
C13 C14 1.388(4)
C13 C18 1.390(4)
C13 N1 1.415(3)
C14 C15 1.391(4)
C14 H14 0.93
C15 C16 1.374(5)
C15 H15 0.93
C16 C17 1.382(4)
C16 H16 0.93
C17 C18 1.382(4)
C17 Br1 1.903(3)
C18 H18 0.93
N1 P1 1.627(2)
N1 H1 0.874(4)
O1 P1 1.4626(19)
O2 P1 1.5769(18)
O3 P1 1.5772(19)
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
N1 H1 O1 2_777 0.874(4) 1.972(7) 2.837(3) 170(3)
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
C6 C1 C2 C3 1.3(5)
O2 C1 C2 C3 178.0(3)
C1 C2 C3 C4 -0.3(6)
C2 C3 C4 C5 -0.6(6)
C3 C4 C5 C6 0.6(6)
C2 C1 C6 C5 -1.3(5)
O2 C1 C6 C5 -178.0(3)
C4 C5 C6 C1 0.4(5)
C12 C7 C8 C9 0.5(5)
O3 C7 C8 C9 179.5(3)
C7 C8 C9 C10 0.2(6)
C8 C9 C10 C11 -0.8(7)
C9 C10 C11 C12 0.6(8)
C8 C7 C12 C11 -0.6(6)
O3 C7 C12 C11 -179.6(4)
C10 C11 C12 C7 0.1(7)
C18 C13 C14 C15 -0.4(4)
N1 C13 C14 C15 178.4(3)
C13 C14 C15 C16 0.1(5)
C14 C15 C16 C17 0.4(5)
C15 C16 C17 C18 -0.7(5)
C15 C16 C17 Br1 -178.3(2)
C16 C17 C18 C13 0.4(4)
Br1 C17 C18 C13 178.0(2)
C14 C13 C18 C17 0.2(4)
N1 C13 C18 C17 -178.7(2)
C14 C13 N1 P1 2.6(4)
C18 C13 N1 P1 -178.6(2)
C6 C1 O2 P1 -90.6(3)
C2 C1 O2 P1 92.6(3)
C8 C7 O3 P1 175.7(2)
C12 C7 O3 P1 -5.2(4)
C1 O2 P1 O1 53.6(2)
C1 O2 P1 O3 175.64(19)
C1 O2 P1 N1 -71.5(2)
C7 O3 P1 O1 -56.5(2)
C7 O3 P1 O2 -179.0(2)
C7 O3 P1 N1 69.0(2)
C13 N1 P1 O1 -177.8(2)
C13 N1 P1 O2 -49.3(3)
C13 N1 P1 O3 53.7(3)
