#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/53/2105327.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_2105327
loop_
_publ_author_name
'Gholivand, Khodayar'
'Valmoozi, Ali A. Ebrahimi'
'Mahzouni, Hamid R.'
_publ_section_title
;
 Structural and electronic aspects of hydrogen bonding in two polymorphs
 of
 butylene-N,N'-bis(O,O'-diarylphosphoramidate)
;
_journal_coeditor_code           PS5019
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              55
_journal_page_last               61
_journal_paper_doi               10.1107/S0108768112048331
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C28 H30 N2 O6 P2'
_chemical_formula_sum            'C28 H30 N2 O6 P2'
_chemical_formula_weight         552.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.659(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6437(9)
_cell_length_b                   14.3801(13)
_cell_length_c                   10.3503(9)
_cell_measurement_reflns_used    2568
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1314.7(2)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10920
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.431
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.8800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2580
_reflns_number_total             3473
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ps5019.cif
_cod_data_source_block           72phcu-prism
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2105327
_cod_database_fobs_code          2105327
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
P P1 0.52065(5) 0.92701(3) 0.81441(5) 0.01914(13) Uani d . 1 1
O O1 0.38529(14) 0.93875(8) 0.84432(13) 0.0229(3) Uani d . 1 1
O O2 0.52895(14) 0.83814(8) 0.72675(13) 0.0231(3) Uani d . 1 1
O O3 0.53081(15) 0.99897(9) 0.70059(13) 0.0244(3) Uani d . 1 1
N N1 0.67619(16) 0.92751(10) 0.95473(16) 0.0201(3) Uani d . 1 1
H H1N 0.6763 0.9553 1.0335 0.024 Uiso d R 1 1
C C1 0.5370(2) 0.74795(12) 0.78237(18) 0.0218(4) Uani d . 1 1
C C2 0.4057(2) 0.70493(14) 0.7737(2) 0.0293(4) Uani d . 1 1
H H2A 0.3117 0.7370 0.7359 0.035 Uiso calc R 1 1
C C3 0.4130(2) 0.61406(14) 0.8210(2) 0.0329(5) Uani d . 1 1
H H3A 0.3234 0.5835 0.8154 0.040 Uiso calc R 1 1
C C4 0.5503(3) 0.56777(14) 0.8763(2) 0.0328(5) Uani d . 1 1
H H4A 0.5550 0.5057 0.9092 0.039 Uiso calc R 1 1
C C5 0.6804(2) 0.61178(13) 0.8835(2) 0.0322(4) Uani d . 1 1
H H5A 0.7743 0.5796 0.9211 0.039 Uiso calc R 1 1
C C6 0.6752(2) 0.70289(13) 0.8363(2) 0.0272(4) Uani d . 1 1
H H6A 0.7645 0.7334 0.8410 0.033 Uiso calc R 1 1
C C7 0.4966(2) 1.09314(12) 0.70346(19) 0.0220(4) Uani d . 1 1
C C8 0.4287(2) 1.13668(13) 0.5740(2) 0.0266(4) Uani d . 1 1
H H8A 0.4057 1.1029 0.4890 0.032 Uiso calc R 1 1
C C9 0.3947(2) 1.23095(14) 0.5708(2) 0.0311(4) Uani d . 1 1
H H9A 0.3490 1.2619 0.4827 0.037 Uiso calc R 1 1
C C10 0.4265(2) 1.27997(13) 0.6941(2) 0.0315(4) Uani d . 1 1
H H10A 0.4004 1.3439 0.6908 0.038 Uiso calc R 1 1
C C11 0.4968(2) 1.23525(13) 0.8227(2) 0.0273(4) Uani d . 1 1
H H11A 0.5206 1.2692 0.9077 0.033 Uiso calc R 1 1
C C12 0.5329(2) 1.14138(13) 0.82859(19) 0.0244(4) Uani d . 1 1
H H12A 0.5814 1.1108 0.9168 0.029 Uiso calc R 1 1
C C13 0.82656(19) 0.91889(12) 0.95086(19) 0.0216(4) Uani d . 1 1
H H13A 0.8138 0.9034 0.8535 0.026 Uiso calc R 1 1
H H13B 0.8817 0.8669 1.0129 0.026 Uiso calc R 1 1
C C14 0.92056(19) 1.00647(12) 0.99734(19) 0.0225(4) Uani d . 1 1
H H14A 0.9275 1.0247 1.0920 0.027 Uiso calc R 1 1
H H14B 0.8695 1.0575 0.9311 0.027 Uiso calc R 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 0.0000 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 P1 O2 . . 117.79(7)
O1 P1 O3 . . 113.79(7)
O2 P1 O3 . . 93.89(7)
O1 P1 N1 . . 113.17(8)
O2 P1 N1 . . 106.00(7)
O3 P1 N1 . . 110.48(8)
C1 O2 P1 . . 120.98(11)
C7 O3 P1 . . 121.77(11)
C13 N1 P1 . . 122.99(12)
C13 N1 H1N . . 114.6
P1 N1 H1N . . 118.4
C2 C1 C6 . . 121.83(17)
C2 C1 O2 . . 119.21(16)
C6 C1 O2 . . 118.85(15)
C1 C2 C3 . . 118.96(18)
C1 C2 H2A . . 120.5
C3 C2 H2A . . 120.5
C4 C3 C2 . . 120.23(18)
C4 C3 H3A . . 119.9
C2 C3 H3A . . 119.9
C5 C4 C3 . . 119.99(19)
C5 C4 H4A . . 120.0
C3 C4 H4A . . 120.0
C4 C5 C6 . . 120.58(19)
C4 C5 H5A . . 119.7
C6 C5 H5A . . 119.7
C1 C6 C5 . . 118.41(17)
C1 C6 H6A . . 120.8
C5 C6 H6A . . 120.8
C8 C7 C12 . . 121.53(17)
C8 C7 O3 . . 116.27(16)
C12 C7 O3 . . 122.17(16)
C7 C8 C9 . . 118.67(18)
C7 C8 H8A . . 120.7
C9 C8 H8A . . 120.7
C10 C9 C8 . . 120.83(18)
C10 C9 H9A . . 119.6
C8 C9 H9A . . 119.6
C9 C10 C11 . . 119.51(18)
C9 C10 H10A . . 120.2
C11 C10 H10A . . 120.2
C10 C11 C12 . . 120.68(18)
C10 C11 H11A . . 119.7
C12 C11 H11A . . 119.7
C7 C12 C11 . . 118.75(17)
C7 C12 H12A . . 120.6
C11 C12 H12A . . 120.6
N1 C13 C14 . . 113.10(14)
N1 C13 H13A . . 109.0
C14 C13 H13A . . 109.0
N1 C13 H13B . . 109.0
C14 C13 H13B . . 109.0
H13A C13 H13B . . 107.8
C13 C14 C14 . 3_777 112.07(17)
C13 C14 H14A . . 109.2
C14 C14 H14A 3_777 . 109.2
C13 C14 H14B . . 109.2
C14 C14 H14B 3_777 . 109.2
H14A C14 H14B . . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 O1 . 1.4672(13)
P1 O2 . 1.5878(12)
P1 O3 . 1.6002(13)
P1 N1 . 1.6158(15)
O2 C1 . 1.408(2)
O3 C7 . 1.397(2)
N1 C13 . 1.472(2)
N1 H1N . 0.9080
C1 C2 . 1.379(3)
C1 C6 . 1.383(3)
C2 C3 . 1.387(3)
C2 H2A . 0.9500
C3 C4 . 1.384(3)
C3 H3A . 0.9500
C4 C5 . 1.380(3)
C4 H4A . 0.9500
C5 C6 . 1.392(3)
C5 H5A . 0.9500
C6 H6A . 0.9500
C7 C8 . 1.382(2)
C7 C12 . 1.385(3)
C8 C9 . 1.392(3)
C8 H8A . 0.9500
C9 C10 . 1.380(3)
C9 H9A . 0.9500
C10 C11 . 1.386(3)
C10 H10A . 0.9500
C11 C12 . 1.389(3)
C11 H11A . 0.9500
C12 H12A . 0.9500
C13 C14 . 1.513(2)
C13 H13A . 0.9900
C13 H13B . 0.9900
C14 C14 3_777 1.522(3)
C14 H14A . 0.9900
C14 H14B . 0.9900
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 H1N O1 3_677 0.91 2.21 3.060(2) 156
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_4
_geom_torsion
O1 P1 O2 C1 . -65.65(15)
O3 P1 O2 C1 . 174.82(13)
N1 P1 O2 C1 . 62.22(14)
O1 P1 O3 C7 . 43.33(15)
O2 P1 O3 C7 . 166.06(13)
N1 P1 O3 C7 . -85.26(14)
O1 P1 N1 C13 . -178.63(12)
O2 P1 N1 C13 . 50.80(14)
O3 P1 N1 C13 . -49.71(14)
P1 O2 C1 C2 . 81.68(19)
P1 O2 C1 C6 . -102.27(17)
C6 C1 C2 C3 . 0.3(3)
O2 C1 C2 C3 . 176.19(17)
C1 C2 C3 C4 . 0.2(3)
C2 C3 C4 C5 . -0.5(3)
C3 C4 C5 C6 . 0.3(3)
C2 C1 C6 C5 . -0.4(3)
O2 C1 C6 C5 . -176.34(17)
C4 C5 C6 C1 . 0.1(3)
P1 O3 C7 C8 . -145.45(14)
P1 O3 C7 C12 . 36.6(2)
C12 C7 C8 C9 . -0.8(3)
O3 C7 C8 C9 . -178.84(16)
C7 C8 C9 C10 . -0.7(3)
C8 C9 C10 C11 . 1.7(3)
C9 C10 C11 C12 . -1.2(3)
C8 C7 C12 C11 . 1.3(3)
O3 C7 C12 C11 . 179.20(16)
C10 C11 C12 C7 . -0.3(3)
P1 N1 C13 C14 . 112.68(15)
N1 C13 C14 C14 3_777 175.84(18)
