#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/95/2229583.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_2229583
loop_
_publ_author_name
'Meng, Fan-Jie'
'Zhao, Chang-Qiu'
_publ_section_title
;
 2-Isopropyl-5-methylcyclohexyl diphenylphosphonamidate
;
_journal_coeditor_code           BQ2285
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o998
_journal_paper_doi               10.1107/S1600536811010580
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C22 H30 N O2 P'
_chemical_formula_sum            'C22 H30 N O2 P'
_chemical_formula_weight         371.44
_chemical_name_common
;
2-Isopropyl-5-methylcyclohexyl diphenylphosphonamidate
;
_chemical_name_systematic
;
N-({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}(phenyl)phosphoryl)aniline
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.0060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6934(8)
_cell_length_b                   5.4716(5)
_cell_length_c                   22.100(2)
_cell_measurement_reflns_used    1942
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.727
_cell_volume                     1031.89(16)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5183
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.249
_refine_ls_abs_structure_details 'Flack (1983), 1550 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0447
_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)+(0.0475P)²+0.0269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2814
_reflns_number_total             3589
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2285.cif
_cod_data_source_block           I
_cod_original_cell_volume        1031.90(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2229583
_cod_database_fobs_code          2229583
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_disorder_assembly
_atom_site_disorder_group
C C1 -0.0896(4) 0.6404(9) 0.08739(15) 0.0830(12) Uani d . 1 . .
H H1A -0.0743 0.4702 0.0778 0.100 Uiso calc R 1 . .
H H1B -0.1840 0.6970 0.0602 0.100 Uiso calc R 1 . .
P P1 0.36057(8) 0.79230(14) 0.29338(3) 0.03738(19) Uani d . 1 . .
C C2 0.5704(3) 0.8039(6) 0.30983(11) 0.0402(6) Uani d . 1 . .
O O2 0.2888(2) 1.0296(3) 0.30075(8) 0.0446(5) Uani d . 1 . .
C C3 0.2897(3) 0.5828(5) 0.39742(11) 0.0351(6) Uani d . 1 . .
O O1 0.3227(2) 0.6846(4) 0.22586(8) 0.0436(5) Uani d . 1 . .
C C4 0.3333(4) 0.7801(7) 0.49563(12) 0.0570(8) Uani d . 1 . .
H H4 0.3754 0.9087 0.5210 0.068 Uiso calc R 1 . .
C C5 0.3513(3) 0.7748(7) 0.43486(11) 0.0459(7) Uani d . 1 . .
H H5 0.4046 0.9000 0.4193 0.055 Uiso calc R 1 . .
N N1 0.3040(3) 0.5712(4) 0.33461(10) 0.0424(6) Uani d . 1 . .
H H6 0.2807 0.4340 0.3161 0.051 Uiso calc R 1 . .
C C7 0.0423(3) 0.6000(7) 0.19730(13) 0.0543(8) Uani d . 1 . .
H H7A 0.0304 0.6289 0.2395 0.065 Uiso calc R 1 . .
H H7B 0.0660 0.4282 0.1934 0.065 Uiso calc R 1 . .
C C8 0.6462(4) 0.9995(6) 0.28841(14) 0.0566(9) Uani d . 1 . .
H H8 0.5884 1.1207 0.2648 0.068 Uiso calc R 1 . .
C C9 0.2115(3) 0.3967(6) 0.42092(13) 0.0458(8) Uani d . 1 . .
H H9 0.1710 0.2659 0.3960 0.055 Uiso calc R 1 . .
C C10 0.1771(3) 0.7509(6) 0.18402(11) 0.0439(8) Uani d . 1 . .
H H10 0.1549 0.9240 0.1899 0.053 Uiso calc R 1 . .
C C11 0.2538(4) 0.5968(7) 0.51885(14) 0.0611(9) Uani d . 1 . .
H H11 0.2408 0.6024 0.5596 0.073 Uiso calc R 1 . .
C C12 0.6582(4) 0.6285(6) 0.34548(13) 0.0507(8) Uani d . 1 . .
H H12 0.6085 0.4972 0.3604 0.061 Uiso calc R 1 . .
C C13 0.2020(4) 0.7132(6) 0.11828(12) 0.0534(9) Uani d . 1 . .
H H13 0.2114 0.5362 0.1132 0.064 Uiso calc R 1 . .
C C14 0.1938(4) 0.4062(7) 0.48197(14) 0.0590(9) Uani d . 1 . .
H H14 0.1406 0.2815 0.4979 0.071 Uiso calc R 1 . .
C C15 0.8088(4) 1.0140(7) 0.30229(16) 0.0660(10) Uani d . 1 . .
H H15 0.8597 1.1438 0.2873 0.079 Uiso calc R 1 . .
C C16 -0.1120(4) 0.6599(7) 0.15376(15) 0.0641(10) Uani d . 1 . .
H H16 -0.1400 0.8292 0.1613 0.077 Uiso calc R 1 . .
C C17 0.3526(5) 0.8226(9) 0.10465(16) 0.0738(11) Uani d . 1 . .
H H17 0.4384 0.7565 0.1356 0.089 Uiso calc R 1 . .
C C18 0.0482(4) 0.7874(9) 0.07536(13) 0.0765(10) Uani d . 1 . .
H H18A 0.0285 0.9595 0.0812 0.092 Uiso calc R 1 . .
H H18B 0.0590 0.7642 0.0329 0.092 Uiso calc R 1 . .
C C19 0.8948(4) 0.8369(7) 0.33812(16) 0.0634(11) Uani d . 1 . .
H H19 1.0035 0.8479 0.3477 0.076 Uiso calc R 1 . .
C C20 0.3841(5) 0.7449(10) 0.04193(16) 0.1023(16) Uani d . 1 . .
H H20A 0.3830 0.5697 0.0392 0.153 Uiso calc R 1 . .
H H20B 0.4847 0.8050 0.0370 0.153 Uiso calc R 1 . .
H H20C 0.3044 0.8109 0.0100 0.153 Uiso calc R 1 . .
C C21 0.3603(7) 1.0937(9) 0.1111(3) 0.1244(19) Uani d . 1 . .
H H21A 0.2736 1.1659 0.0835 0.187 Uiso calc R 1 . .
H H21B 0.4567 1.1518 0.1013 0.187 Uiso calc R 1 . .
H H21C 0.3555 1.1379 0.1527 0.187 Uiso calc R 1 . .
C C22 -0.2440(5) 0.4933(9) 0.1665(2) 0.0947(14) Uani d . 1 . .
H H22A -0.2187 0.3263 0.1595 0.142 Uiso calc R 1 . .
H H22B -0.3403 0.5366 0.1396 0.142 Uiso calc R 1 . .
H H22C -0.2556 0.5128 0.2086 0.142 Uiso calc R 1 . .
C C23 0.8201(4) 0.6464(7) 0.35934(15) 0.0633(10) Uani d . 1 . .
H H23 0.8783 0.5267 0.3834 0.076 Uiso calc R 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
_geom_angle_publ_flag
C18 C1 C16 . . 112.6(3) ?
C18 C1 H1A . . 109.1 ?
C16 C1 H1A . . 109.1 ?
C18 C1 H1B . . 109.1 ?
C16 C1 H1B . . 109.1 ?
H1A C1 H1B . . 107.8 ?
O2 P1 O1 . . 114.83(11) ?
O2 P1 N1 . . 114.34(11) ?
O1 P1 N1 . . 102.61(11) ?
O2 P1 C2 . . 112.65(14) ?
O1 P1 C2 . . 103.04(11) ?
N1 P1 C2 . . 108.29(14) ?
C12 C2 C8 . . 119.1(3) ?
C12 C2 P1 . . 121.5(2) ?
C8 C2 P1 . . 119.3(2) ?
C9 C3 C5 . . 119.9(2) ?
C9 C3 N1 . . 118.5(3) ?
C5 C3 N1 . . 121.6(3) ?
C10 O1 P1 . . 120.25(16) ?
C11 C4 C5 . . 120.4(3) ?
C11 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C3 C5 C4 . . 119.7(3) ?
C3 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C3 N1 P1 . . 126.9(2) ?
C3 N1 H6 . . 116.5 ?
P1 N1 H6 . . 116.5 ?
C10 C7 C16 . . 112.4(3) ?
C10 C7 H7A . . 109.1 ?
C16 C7 H7A . . 109.1 ?
C10 C7 H7B . . 109.1 ?
C16 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.9 ?
C2 C8 C15 . . 119.9(3) ?
C2 C8 H8 . . 120.1 ?
C15 C8 H8 . . 120.1 ?
C3 C9 C14 . . 119.5(3) ?
C3 C9 H9 . . 120.2 ?
C14 C9 H9 . . 120.2 ?
O1 C10 C7 . . 110.6(2) ?
O1 C10 C13 . . 107.8(2) ?
C7 C10 C13 . . 111.6(2) ?
O1 C10 H10 . . 108.9 ?
C7 C10 H10 . . 108.9 ?
C13 C10 H10 . . 108.9 ?
C14 C11 C4 . . 119.8(3) ?
C14 C11 H11 . . 120.1 ?
C4 C11 H11 . . 120.1 ?
C2 C12 C23 . . 120.4(3) ?
C2 C12 H12 . . 119.8 ?
C23 C12 H12 . . 119.8 ?
C17 C13 C10 . . 114.8(3) ?
C17 C13 C18 . . 117.0(3) ?
C10 C13 C18 . . 106.7(2) ?
C17 C13 H13 . . 105.8 ?
C10 C13 H13 . . 105.8 ?
C18 C13 H13 . . 105.8 ?
C11 C14 C9 . . 120.6(3) ?
C11 C14 H14 . . 119.7 ?
C9 C14 H14 . . 119.7 ?
C19 C15 C8 . . 120.3(3) ?
C19 C15 H15 . . 119.9 ?
C8 C15 H15 . . 119.9 ?
C1 C16 C7 . . 109.5(3) ?
C1 C16 C22 . . 112.0(3) ?
C7 C16 C22 . . 110.7(3) ?
C1 C16 H16 . . 108.2 ?
C7 C16 H16 . . 108.2 ?
C22 C16 H16 . . 108.2 ?
C21 C17 C20 . . 110.6(4) ?
C21 C17 C13 . . 113.4(4) ?
C20 C17 C13 . . 112.4(4) ?
C21 C17 H17 . . 106.6 ?
C20 C17 H17 . . 106.6 ?
C13 C17 H17 . . 106.6 ?
C1 C18 C13 . . 112.1(3) ?
C1 C18 H18A . . 109.2 ?
C13 C18 H18A . . 109.2 ?
C1 C18 H18B . . 109.2 ?
C13 C18 H18B . . 109.2 ?
H18A C18 H18B . . 107.9 ?
C23 C19 C15 . . 119.7(3) ?
C23 C19 H19 . . 120.2 ?
C15 C19 H19 . . 120.2 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C17 C21 H21A . . 109.5 ?
C17 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C17 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C16 C22 H22A . . 109.5 ?
C16 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C16 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C19 C23 C12 . . 120.7(3) ?
C19 C23 H23 . . 119.7 ?
C12 C23 H23 . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C18 . 1.508(5) ?
C1 C16 . 1.520(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
P1 O2 . 1.463(2) ?
P1 O1 . 1.5795(19) ?
P1 N1 . 1.645(2) ?
P1 C2 . 1.792(3) ?
C2 C12 . 1.376(4) ?
C2 C8 . 1.386(4) ?
C3 C9 . 1.380(4) ?
C3 C5 . 1.380(4) ?
C3 N1 . 1.419(3) ?
O1 C10 . 1.463(3) ?
C4 C11 . 1.372(5) ?
C4 C5 . 1.382(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
N1 H6 . 0.8600 ?
C7 C10 . 1.507(4) ?
C7 C16 . 1.530(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C15 . 1.390(4) ?
C8 H8 . 0.9300 ?
C9 C14 . 1.388(4) ?
C9 H9 . 0.9300 ?
C10 C13 . 1.523(4) ?
C10 H10 . 0.9800 ?
C11 C14 . 1.364(5) ?
C11 H11 . 0.9300 ?
C12 C23 . 1.386(4) ?
C12 H12 . 0.9300 ?
C13 C17 . 1.521(5) ?
C13 C18 . 1.539(4) ?
C13 H13 . 0.9800 ?
C14 H14 . 0.9300 ?
C15 C19 . 1.378(5) ?
C15 H15 . 0.9300 ?
C16 C22 . 1.533(5) ?
C16 H16 . 0.9800 ?
C17 C21 . 1.490(7) ?
C17 C20 . 1.524(5) ?
C17 H17 . 0.9800 ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C23 . 1.358(5) ?
C19 H19 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
C23 H23 . 0.9300 ?
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 H6 O2 1_545 0.86 2.24 3.053(3) 157
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P1 C2 C12 . . . . 134.9(2) ?
O1 P1 C2 C12 . . . . -100.8(2) ?
N1 P1 C2 C12 . . . . 7.4(3) ?
O2 P1 C2 C8 . . . . -42.3(3) ?
O1 P1 C2 C8 . . . . 82.0(2) ?
N1 P1 C2 C8 . . . . -169.8(2) ?
O2 P1 O1 C10 . . . . -27.3(2) ?
N1 P1 O1 C10 . . . . 97.4(2) ?
C2 P1 O1 C10 . . . . -150.1(2) ?
C9 C3 C5 C4 . . . . -0.4(4) ?
N1 C3 C5 C4 . . . . 179.4(3) ?
C11 C4 C5 C3 . . . . -0.5(5) ?
C9 C3 N1 P1 . . . . 167.3(2) ?
C5 C3 N1 P1 . . . . -12.5(4) ?
O2 P1 N1 C3 . . . . -45.0(3) ?
O1 P1 N1 C3 . . . . -170.0(2) ?
C2 P1 N1 C3 . . . . 81.5(2) ?
C12 C2 C8 C15 . . . . 1.0(4) ?
P1 C2 C8 C15 . . . . 178.2(2) ?
C5 C3 C9 C14 . . . . 0.8(4) ?
N1 C3 C9 C14 . . . . -179.0(3) ?
P1 O1 C10 C7 . . . . -81.0(3) ?
P1 O1 C10 C13 . . . . 156.7(2) ?
C16 C7 C10 O1 . . . . -178.9(2) ?
C16 C7 C10 C13 . . . . -58.9(3) ?
C5 C4 C11 C14 . . . . 0.9(5) ?
C8 C2 C12 C23 . . . . -0.5(4) ?
P1 C2 C12 C23 . . . . -177.7(2) ?
O1 C10 C13 C17 . . . . -47.9(4) ?
C7 C10 C13 C17 . . . . -169.6(3) ?
O1 C10 C13 C18 . . . . -179.3(3) ?
C7 C10 C13 C18 . . . . 59.1(3) ?
C4 C11 C14 C9 . . . . -0.5(5) ?
C3 C9 C14 C11 . . . . -0.4(5) ?
C2 C8 C15 C19 . . . . -1.1(5) ?
C18 C1 C16 C7 . . . . -52.1(5) ?
C18 C1 C16 C22 . . . . -175.3(3) ?
C10 C7 C16 C1 . . . . 53.0(4) ?
C10 C7 C16 C22 . . . . 177.0(3) ?
C10 C13 C17 C21 . . . . -62.8(5) ?
C18 C13 C17 C21 . . . . 63.4(5) ?
C10 C13 C17 C20 . . . . 170.8(3) ?
C18 C13 C17 C20 . . . . -63.0(5) ?
C16 C1 C18 C13 . . . . 57.0(5) ?
C17 C13 C18 C1 . . . . 171.6(3) ?
C10 C13 C18 C1 . . . . -58.3(4) ?
C8 C15 C19 C23 . . . . 0.7(5) ?
C15 C19 C23 C12 . . . . -0.2(5) ?
C2 C12 C23 C19 . . . . 0.1(5) ?
