#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218389.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_7218389
loop_
_publ_author_name
'Pourayoubi, Mehrdad'
'Toghraee, Maryam'
'Zhu, Jianfeng'
'Dušek, Michal'
'Bereciartua, Pablo J.'
'Eigner, Václav'
_publ_section_title
;
 Database analysis of hydrogen bond patterns in phosphoric triamides
 completed with seven new compounds: a crystallographic and15N NMR study
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10870
_journal_paper_doi               10.1039/C4CE01793E
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C12 H20 N3 O1 P1'
_chemical_formula_sum            'C12 H20 N3 O P'
_chemical_formula_weight         253.3
_chemical_name_systematic        ' ?'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 93.386(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3055(3)
_cell_length_b                   10.8856(3)
_cell_length_c                   12.9523(4)
_cell_measurement_reflns_used    10695
_cell_measurement_temperature    120.00(14)
_cell_measurement_theta_max      66.97
_cell_measurement_theta_min      4.06
_cell_volume                     1309.73(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21603
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         5.31
_exptl_absorpt_coefficient_mu    1.77
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2841
_exptl_crystal_description       blocky
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.229
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    2.31
_refine_ls_goodness_of_fit_ref   2.19
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    0
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.0180
_refine_ls_shift/su_mean         0.0011
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0383
_refine_ls_wR_factor_ref         0.0391
_reflns_number_gt                2029
_reflns_number_total             2327
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            c4ce01793e2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218388--7218395.cif.
;
_cod_original_formula_sum        'C12 H20 N3 O1 P1'
_cod_database_code               7218389
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z
3 -x,-y,-z
4 x+1/2,-y+1/2,z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
P1 P 0.17723(4) 0.65203(3) 0.02508(3) Uani 0.01622(12) 4 1 d
O1 O 0.03302(10) 0.64497(9) 0.06773(8) Uani 0.0209(3) 4 1 d
N1 N 0.19222(13) 0.75455(11) -0.06644(9) Uani 0.0184(4) 4 1 d
N2 N 0.21753(13) 0.51963(11) -0.02772(9) Uani 0.0174(4) 4 1 d
N3 N 0.30325(13) 0.69017(11) 0.11423(9) Uani 0.0186(4) 4 1 d
C1 C 0.42017(18) 0.60524(15) -0.26648(12) Uani 0.0278(5) 4 1 d
C2 C 0.29448(16) 0.74057(13) -0.14887(11) Uani 0.0192(4) 4 1 d
C3 C 0.32745(16) 0.51942(13) -0.10537(11) Uani 0.0199(5) 4 1 d
C4 C 0.15438(17) 0.58085(15) -0.25334(12) Uani 0.0265(5) 4 1 d
C5 C 0.29681(15) 0.61114(13) -0.19398(11) Uani 0.0188(4) 4 1 d
H1c1 H 0.42016 0.526428 -0.299737 Uiso 0.0333 4 1 d
H2c1 H 0.407905 0.668525 -0.317869 Uiso 0.0333 4 1 d
H3c1 H 0.510021 0.61707 -0.227421 Uiso 0.0333 4 1 d
H1c2 H 0.389501 0.762478 -0.122251 Uiso 0.023 4 1 d
H2c2 H 0.271042 0.798467 -0.203182 Uiso 0.023 4 1 d
H1c3 H 0.335909 0.438207 -0.133264 Uiso 0.0239 4 1 d
H2c3 H 0.420167 0.536454 -0.072001 Uiso 0.0239 4 1 d
H1c4 H 0.076475 0.592409 -0.208924 Uiso 0.0319 4 1 d
H2c4 H 0.141468 0.634137 -0.312216 Uiso 0.0319 4 1 d
H3c4 H 0.155728 0.496975 -0.276169 Uiso 0.0319 4 1 d
H1n1 H 0.1902(17) 0.8311(4) -0.0473(12) Uiso 0.0221 4 1 d
H1n2 H 0.1390(9) 0.4800(13) -0.0464(12) Uiso 0.0209 4 1 d
H1n3 H 0.3722(12) 0.7372(12) 0.0948(12) Uiso 0.0223 4 1 d
C6a C 0.4133(8) 0.7007(6) 0.2862(6) Uani 0.0203(14) 4 0.553(2) d
C7a C 0.4280(6) 0.6658(5) 0.3891(4) Uani 0.0210(15) 4 0.553(2) d
C8a C 0.3380(6) 0.5762(5) 0.4231(2) Uani 0.0245(18) 4 0.553(2) d
C9a C 0.3090(15) 0.6477(13) 0.2175(4) Uani 0.0152(15) 4 0.553(2) d
C10a C 0.2375(6) 0.5204(5) 0.3557(4) Uani 0.0229(14) 4 0.553(2) d
C11a C 0.2223(7) 0.5560(6) 0.2520(5) Uani 0.0147(12) 4 0.553(2) d
C12a C 0.5415(4) 0.7277(3) 0.4603(2) Uani 0.0416(9) 4 0.553(2) d
H1c6a H 0.476083 0.762657 0.261352 Uiso 0.0244 4 0.553(2) d
H1c8a H 0.345012 0.552141 0.494503 Uiso 0.0294 4 0.553(2) d
H1c10a H 0.177388 0.456413 0.380468 Uiso 0.0274 4 0.553(2) d
H1c11a H 0.152218 0.516974 0.205507 Uiso 0.0176 4 0.553(2) d
H1c12a H 0.550086 0.684717 0.525104 Uiso 0.0499 4 0.553(2) d
H2c12a H 0.632365 0.726321 0.428873 Uiso 0.0499 4 0.553(2) d
H3c12a H 0.51384 0.811302 0.472036 Uiso 0.0499 4 0.553(2) d
C6b C 0.2464(9) 0.5737(7) 0.2705(6) Uani 0.0203(14) 4 0.447(2) d
C7b C 0.2705(7) 0.5465(6) 0.3745(5) Uani 0.0210(15) 4 0.447(2) d
C8b C 0.3787(7) 0.6078(6) 0.4300(4) Uani 0.0245(18) 4 0.447(2) d
C9b C 0.3301(15) 0.6607(12) 0.2215(6) Uani 0.0152(15) 4 0.447(2) d
C10b C 0.4594(7) 0.6964(6) 0.3836(5) Uani 0.0229(14) 4 0.447(2) d
C11b C 0.4355(8) 0.7236(7) 0.2786(5) Uani 0.0147(13) 4 0.447(2) d
C12b C 0.1778(5) 0.4500(4) 0.4232(3) Uani 0.0416(10) 4 0.447(2) d
H1c6b H 0.170623 0.532038 0.231082 Uiso 0.0244 4 0.447(2) d
H1c8b H 0.398498 0.588808 0.501783 Uiso 0.0294 4 0.447(2) d
H1c10b H 0.532709 0.73993 0.424043 Uiso 0.0274 4 0.447(2) d
H1c11b H 0.491875 0.785203 0.246669 Uiso 0.0176 4 0.447(2) d
H1c12b H 0.19558 0.451419 0.496934 Uiso 0.0499 4 0.447(2) d
H2c12b H 0.078086 0.467384 0.406107 Uiso 0.0499 4 0.447(2) d
H3c12b H 0.201226 0.370349 0.397221 Uiso 0.0499 4 0.447(2) d
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.2955 0.4335 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 P1 N1 114.96(6)
O1 P1 N2 110.02(6)
O1 P1 N3 111.95(6)
N1 P1 N2 105.31(6)
N1 P1 N3 104.32(6)
N2 P1 N3 109.93(6)
P1 N1 C2 122.51(10)
P1 N1 H1n1 116.2(10)
C2 N1 H1n1 109.3(10)
P1 N2 C3 117.90(9)
P1 N2 H1n2 109.9(8)
C3 N2 H1n2 114.5(10)
P1 N3 H1n3 116.8(9)
P1 N3 C9a 124.5(6)
H1n3 N3 C9a 118.7(11)
C5 C1 H1c1 109.47
C5 C1 H2c1 109.47
C5 C1 H3c1 109.47
H1c1 C1 H2c1 109.47
H1c1 C1 H3c1 109.47
H2c1 C1 H3c1 109.47
N1 C2 C5 113.31(12)
N1 C2 H1c2 109.47
N1 C2 H2c2 109.47
C5 C2 H1c2 109.47
C5 C2 H2c2 109.47
H1c2 C2 H2c2 105.34
N2 C3 C5 113.75(12)
N2 C3 H1c3 109.47
N2 C3 H2c3 109.47
C5 C3 H1c3 109.47
C5 C3 H2c3 109.47
H1c3 C3 H2c3 104.82
C5 C4 H1c4 109.47
C5 C4 H2c4 109.47
C5 C4 H3c4 109.47
H1c4 C4 H2c4 109.47
H1c4 C4 H3c4 109.47
H2c4 C4 H3c4 109.47
C1 C5 C2 107.61(12)
C1 C5 C3 108.62(12)
C1 C5 C4 110.04(12)
C2 C5 C3 108.69(11)
C2 C5 C4 111.12(12)
C3 C5 C4 110.67(12)
C7a C6a C9a 121.5(7)
C7a C6a H1c6a 119.23
C9a C6a H1c6a 119.23
C6a C7a C8a 118.4(5)
C6a C7a C12a 119.2(5)
C8a C7a C12a 122.4(4)
C7a C8a C10a 120.8(4)
C7a C8a H1c8a 119.6
C10a C8a H1c8a 119.6
N3 C9a C6a 116.9(10)
N3 C9a C11a 123.7(8)
C6a C9a C11a 119.4(6)
C8a C10a C11a 120.8(5)
C8a C10a H1c10a 119.62
C11a C10a H1c10a 119.61
C9a C11a C10a 119.1(6)
C9a C11a H1c11a 120.46
C10a C11a H1c11a 120.46
C7a C12a H1c12a 109.47
C7a C12a H2c12a 109.47
C7a C12a H3c12a 109.47
H1c12a C12a H2c12a 109.47
H1c12a C12a H3c12a 109.47
H2c12a C12a H3c12a 109.47
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4831(11)
P1 N1 1.6399(12)
P1 N2 1.6479(12)
P1 N3 1.6495(12)
N1 C2 1.4794(19)
N1 H1n1 0.870(6)
N2 C3 1.4763(19)
N2 H1n2 0.870(11)
N3 H1n3 0.870(12)
N3 C9a 1.413(6)
C1 C5 1.527(2)
C1 H1c1 0.96
C1 H2c1 0.96
C1 H3c1 0.96
C2 C5 1.526(2)
C2 H1c2 0.96
C2 H2c2 0.96
C3 C5 1.535(2)
C3 H1c3 0.96
C3 H2c3 0.96
C4 C5 1.528(2)
C4 H1c4 0.96
C4 H2c4 0.96
C4 H3c4 0.96
C6a C7a 1.385(10)
C6a C9a 1.402(13)
C6a H1c6a 0.96
C7a C8a 1.375(8)
C7a C12a 1.519(6)
C8a C10a 1.381(7)
C8a H1c8a 0.96
C9a C11a 1.375(15)
C10a C11a 1.397(8)
C10a H1c10a 0.96
C11a H1c11a 0.96
C12a H1c12a 0.96
C12a H2c12a 0.96
C12a H3c12a 0.96
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 H1n1 N2 2_555 0.870(6) 2.407(9) 3.2246(17) 156.7(13)
N2 H1n2 O1 3_565 0.870(11) 2.107(11) 2.9619(15) 167.3(13)
N3 H1n3 O1 4_565 0.870(12) 2.017(12) 2.8822(16) 172.8(14)
C11a H1c11a O1 . 0.96 2.47 3.040(6) 117.52
