#------------------------------------------------------------------------------
#$Date: 2021-07-23 07:30:32 +0300 (Fri, 23 Jul 2021) $
#$Revision: 267720 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158189.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_7158189
loop_
_publ_author_name
'Tajti, \'Ad\'am'
'Szab\'o, K\'armen Em\>oke'
'Popovics-T\'oth, N\'ora'
'Iskanderov, Javad'
'Perdih, Franc'
'Hackler, L\'aszl\'o'
'Kari, Be\'ata'
'Puskas, Laszlo G.'
'B\'alint, Erika'
_publ_section_title
;
 PMDTA-Catalyzed multicomponent synthesis and biological activity of
 2-amino-4H-chromenes containing phosphonate or phosphine oxide moiety
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB01204E
_journal_year                    2021
_chemical_formula_moiety         'C24 H21 N2 O2 P'
_chemical_formula_sum            'C24 H21 N2 O2 P'
_chemical_formula_weight         400.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-13 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                115.027(7)
_cell_angle_beta                 91.058(5)
_cell_angle_gamma                113.010(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0000(5)
_cell_length_b                   11.1653(8)
_cell_length_c                   12.3858(7)
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.2170
_cell_measurement_theta_min      3.2980
_cell_volume                     1012.50(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.521
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.4120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3712
_reflns_number_total             4649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01204e2.cif
_cod_data_source_block           Structure-14b
_cod_original_cell_volume        1012.50(13)
_cod_database_code               7158189
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_file
;
TITL mob722.res in P-1
    mob722.res
    created by SHELXL-2018/3 at 10:49:00 on 13-Aug-2019
CELL 0.71073 9 11.1653 12.3858 115.027 91.058 113.01
ZERR 2 0.0005 0.0008 0.0007 0.007 0.005 0.006
LATT 1
SFAC C H N O P
UNIT 48 42 4 4 2
EQIV $1 1-X,1-Y,1-Z
EQIV $2 2-X,1-Y,1-Z

L.S. 10
PLAN  20
SIZE 0.5 0.3 0.3
TEMP -123
HTAB N2 N1_$1
HTAB N2 O1_$2
BOND $H
CONF
fmap 2
acta
SHEL 20.4 0.77
REM <olex2.extras>
REM <HklSrc "%.\\mob722.hkl">
REM </olex2.extras>

WGHT    0.044700    0.412000
FVAR       0.54587
P1    5    0.798479    0.334701    0.699947    11.00000    0.01930    0.01998 =
         0.02177    0.00941    0.00519    0.00995
O1    4    0.969481    0.436815    0.707209    11.00000    0.01993    0.02725 =
         0.02980    0.01321    0.00656    0.00813
O2    4    0.892076    0.318681    0.405243    11.00000    0.02422    0.02743 =
         0.03044    0.01647    0.01083    0.01670
N1    3    0.387022    0.332593    0.496027    11.00000    0.02587    0.03318 =
         0.04678    0.02349    0.01133    0.01753
N2    3    0.769330    0.454583    0.397659    11.00000    0.02625    0.03403 =
         0.03388    0.02222    0.01331    0.02009
H2B   2    0.712976    0.502415    0.427005    11.00000   -1.20000
H2A   2    0.856726    0.489495    0.364942    11.00000   -1.20000
C1    1    0.681357    0.203698    0.540877    11.00000    0.01895    0.01996 =
         0.02248    0.01049    0.00445    0.00961
AFIX  13
H1    2    0.573940    0.128961    0.540849    11.00000   -1.20000
AFIX   0
C2    1    0.647416    0.288661    0.482791    11.00000    0.01857    0.02247 =
         0.02339    0.01099    0.00479    0.01206
C3    1    0.764088    0.355048    0.431017    11.00000    0.01915    0.02273 =
         0.02161    0.00922    0.00200    0.01135
C4    1    0.877828    0.188406    0.402462    11.00000    0.02180    0.02279 =
         0.02187    0.00887    0.00138    0.01229
C5    1    0.777134    0.126465    0.466388    11.00000    0.01802    0.02093 =
         0.02094    0.00675    0.00051    0.00986
C6    1    0.970660    0.125014    0.333183    11.00000    0.02909    0.03854 =
         0.02464    0.01486    0.00971    0.02183
AFIX  43
H6    2    1.041962    0.171296    0.292679    11.00000   -1.20000
AFIX   0
C7    1    0.958406   -0.006801    0.323572    11.00000    0.03548    0.03520 =
         0.02419    0.00763    0.00555    0.02599
AFIX  43
H7    2    1.020314   -0.052136    0.275133    11.00000   -1.20000
AFIX   0
C8    1    0.856604   -0.072678    0.384077    11.00000    0.03062    0.02307 =
         0.02964    0.00719   -0.00026    0.01634
AFIX  43
H8    2    0.847142   -0.163933    0.376180    11.00000   -1.20000
AFIX   0
C9    1    0.768296   -0.005506    0.456304    11.00000    0.02047    0.02048 =
         0.02773    0.00905    0.00017    0.00967
AFIX  43
H9    2    0.700829   -0.049912    0.499536    11.00000   -1.20000
AFIX   0
C10   1    0.504583    0.314224    0.491726    11.00000    0.02150    0.02128 =
         0.02821    0.01379    0.00518    0.00874
C11   1    0.675505    0.430295    0.764112    11.00000    0.02382    0.02162 =
         0.01940    0.00709    0.00426    0.01207
C12   1    0.715746    0.563587    0.763044    11.00000    0.02793    0.02264 =
         0.03064    0.01150    0.00743    0.01052
AFIX  43
H12   2    0.809460    0.603784    0.733402    11.00000   -1.20000
AFIX   0
C13   1    0.619100    0.637849    0.805242    11.00000    0.03750    0.02377 =
         0.03453    0.01123    0.00655    0.01745
AFIX  43
H13   2    0.647231    0.728386    0.803722    11.00000   -1.20000
AFIX   0
C14   1    0.482184    0.581783    0.849545    11.00000    0.03300    0.03018 =
         0.02292    0.00604    0.00351    0.02051
C15   1    0.441633    0.447991    0.849100    11.00000    0.02695    0.03459 =
         0.02826    0.01265    0.00984    0.01677
AFIX  43
H15   2    0.347528    0.407737    0.878380    11.00000   -1.20000
AFIX   0
C16   1    0.536775    0.372157    0.806427    11.00000    0.02976    0.02599 =
         0.02721    0.01293    0.00921    0.01508
AFIX  43
H16   2    0.506924    0.280474    0.806189    11.00000   -1.20000
AFIX   0
C17   1    0.379274    0.663846    0.898975    11.00000    0.04336    0.04262 =
         0.03633    0.01230    0.00984    0.03101
AFIX 137
H17A  2    0.414839    0.748036    0.882287    11.00000   -1.50000
H17B  2    0.393897    0.698942    0.987347    11.00000   -1.50000
H17C  2    0.262324    0.597799    0.859359    11.00000   -1.50000
AFIX   0
C18   1    0.796589    0.234588    0.782674    11.00000    0.02354    0.02390 =
         0.02199    0.00974    0.00694    0.01543
C19   1    0.931255    0.303322    0.880305    11.00000    0.02545    0.02534 =
         0.02648    0.00853    0.00310    0.01273
AFIX  43
H19   2    1.022613    0.392039    0.893921    11.00000   -1.20000
AFIX   0
C20   1    0.932071    0.242617    0.957314    11.00000    0.03650    0.03513 =
         0.02197    0.00831    0.00007    0.02084
AFIX  43
H20   2    1.024093    0.290907    1.023641    11.00000   -1.20000
AFIX   0
C21   1    0.801101    0.112670    0.939437    11.00000    0.04318    0.03330 =
         0.02397    0.01382    0.00989    0.02606
C22   1    0.670017    0.042463    0.840025    11.00000    0.03432    0.02495 =
         0.03019    0.01460    0.00937    0.01502
AFIX  43
H22   2    0.581225   -0.048534    0.824557    11.00000   -1.20000
AFIX   0
C23   1    0.666161    0.102653    0.762766    11.00000    0.02514    0.02364 =
         0.02490    0.00952    0.00304    0.01152
AFIX  43
H23   2    0.574305    0.053678    0.696177    11.00000   -1.20000
AFIX   0
C24   1    0.800191    0.053602    1.029358    11.00000    0.06692    0.05111 =
         0.03577    0.02640    0.00952    0.03380
AFIX 137
H24A  2    0.873187    0.004855    1.013739    11.00000   -1.50000
H24B  2    0.687316   -0.017373    1.019728    11.00000   -1.50000
H24C  2    0.839481    0.135096    1.112800    11.00000   -1.50000
AFIX   0
HKLF 4




REM  mob722.res in P-1
REM wR2 = 0.1114, GooF = S = 1.030, Restrained GooF = 1.030 for all data
REM R1 = 0.0433 for 3712 Fo > 4sig(Fo) and 0.0593 for all 4649 data
REM 270 parameters refined using 0 restraints

END

WGHT      0.0447      0.4093

REM Highest difference peak  0.376,  deepest hole -0.357,  1-sigma level  0.052
Q1    1   0.7142  0.2497  0.6089  11.00000  0.05    0.38
Q2    1   0.7409  0.3928  0.7536  11.00000  0.05    0.30
Q3    1   0.7883  0.2798  0.7508  11.00000  0.05    0.26
Q4    1   0.7296  0.1593  0.5096  11.00000  0.05    0.24
Q5    1   0.6059  0.3267  0.5090  11.00000  0.05    0.23
Q6    1   0.4614  0.7683  0.9531  11.00000  0.05    0.22
Q7    1   0.7348  0.3615  0.5014  11.00000  0.05    0.22
Q8    1   0.7006  0.5013  0.7794  11.00000  0.05    0.21
Q9    1   0.7474  0.0507  0.4568  11.00000  0.05    0.21
Q10   1   0.8767  0.1251  0.3435  11.00000  0.05    0.21
Q11   1   0.6722  0.2532  0.5231  11.00000  0.05    0.20
Q12   1   0.7546  0.0679  0.8743  11.00000  0.05    0.19
Q13   1   0.9190  0.1188  1.0761  11.00000  0.05    0.19
Q14   1   0.7532 -0.0544  0.9882  11.00000  0.05    0.19
Q15   1   0.4563  0.6250  0.8898  11.00000  0.05    0.18
Q16   1   0.7925  0.0828  0.9775  11.00000  0.05    0.18
Q17   1   0.8425  0.2831  0.8457  11.00000  0.05    0.18
Q18   1   0.5001  0.5346  0.8873  11.00000  0.05    0.18
Q19   1   0.8762  0.2459  0.3918  11.00000  0.05    0.18
Q20   1   0.7822 -0.0576  0.4037  11.00000  0.05    0.18
;
_shelx_res_checksum              26300
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.79848(5) 0.33470(5) 0.69995(4) 0.02001(12) Uani 1 1 d . . . . .
O1 O 0.96948(15) 0.43682(13) 0.70721(11) 0.0265(3) Uani 1 1 d . . . . .
O2 O 0.89208(15) 0.31868(13) 0.40524(11) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.3870(2) 0.33259(18) 0.49603(16) 0.0317(4) Uani 1 1 d . . . . .
N2 N 0.7693(2) 0.45458(18) 0.39766(14) 0.0264(3) Uani 1 1 d . . . . .
H2B H 0.713(3) 0.502(2) 0.4270(19) 0.032 Uiso 1 1 d . U . . .
H2A H 0.857(3) 0.489(2) 0.3649(18) 0.032 Uiso 1 1 d . U . . .
C1 C 0.6814(2) 0.20370(18) 0.54088(15) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.573940 0.128961 0.540849 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6474(2) 0.28866(18) 0.48279(15) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.7641(2) 0.35505(18) 0.43102(15) 0.0209(3) Uani 1 1 d . . . . .
C4 C 0.8778(2) 0.18841(18) 0.40246(15) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.7771(2) 0.12646(18) 0.46639(15) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.9707(2) 0.1250(2) 0.33318(16) 0.0282(4) Uani 1 1 d . . . . .
H6 H 1.041962 0.171296 0.292679 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9584(2) -0.0068(2) 0.32357(17) 0.0304(4) Uani 1 1 d . . . . .
H7 H 1.020314 -0.052136 0.275133 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8566(2) -0.0727(2) 0.38408(16) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.847142 -0.163933 0.376180 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7683(2) -0.00551(18) 0.45630(16) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.700829 -0.049912 0.499536 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5046(2) 0.31422(18) 0.49173(16) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.6755(2) 0.43029(18) 0.76411(15) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.7157(2) 0.56359(19) 0.76304(17) 0.0276(4) Uani 1 1 d . . . . .
H12 H 0.809460 0.603784 0.733402 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6191(2) 0.6378(2) 0.80524(17) 0.0315(4) Uani 1 1 d . . . . .
H13 H 0.647231 0.728386 0.803722 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4822(2) 0.5818(2) 0.84954(16) 0.0289(4) Uani 1 1 d . . . . .
C15 C 0.4416(2) 0.4480(2) 0.84910(17) 0.0295(4) Uani 1 1 d . . . . .
H15 H 0.347528 0.407737 0.878380 0.035 Uiso 1 1 calc R U . . .
C16 C 0.5368(2) 0.3722(2) 0.80643(16) 0.0264(4) Uani 1 1 d . . . . .
H16 H 0.506924 0.280474 0.806189 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3793(3) 0.6638(2) 0.89898(19) 0.0389(5) Uani 1 1 d . . . . .
H17A H 0.414839 0.748036 0.882287 0.058 Uiso 1 1 calc R U . . .
H17B H 0.393897 0.698942 0.987347 0.058 Uiso 1 1 calc R U . . .
H17C H 0.262324 0.597799 0.859359 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7966(2) 0.23459(18) 0.78267(15) 0.0217(4) Uani 1 1 d . . . . .
C19 C 0.9313(2) 0.3033(2) 0.88031(16) 0.0266(4) Uani 1 1 d . . . . .
H19 H 1.022613 0.392039 0.893921 0.032 Uiso 1 1 calc R U . . .
C20 C 0.9321(2) 0.2426(2) 0.95731(16) 0.0315(4) Uani 1 1 d . . . . .
H20 H 1.024093 0.290907 1.023641 0.038 Uiso 1 1 calc R U . . .
C21 C 0.8011(3) 0.1127(2) 0.93944(16) 0.0300(4) Uani 1 1 d . . . . .
C22 C 0.6700(2) 0.0425(2) 0.84002(17) 0.0284(4) Uani 1 1 d . . . . .
H22 H 0.581225 -0.048534 0.824557 0.034 Uiso 1 1 calc R U . . .
C23 C 0.6662(2) 0.10265(19) 0.76277(16) 0.0250(4) Uani 1 1 d . . . . .
H23 H 0.574305 0.053678 0.696177 0.030 Uiso 1 1 calc R U . . .
C24 C 0.8002(3) 0.0536(3) 1.0294(2) 0.0461(6) Uani 1 1 d . . . . .
H24A H 0.873187 0.004855 1.013739 0.069 Uiso 1 1 calc R U . . .
H24B H 0.687316 -0.017373 1.019728 0.069 Uiso 1 1 calc R U . . .
H24C H 0.839481 0.135096 1.112800 0.069 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0193(2) 0.0200(2) 0.0218(2) 0.00941(18) 0.00519(17) 0.00995(18)
O1 0.0199(6) 0.0273(7) 0.0298(7) 0.0132(5) 0.0066(5) 0.0081(5)
O2 0.0242(6) 0.0274(6) 0.0304(7) 0.0165(5) 0.0108(5) 0.0167(5)
N1 0.0259(8) 0.0332(9) 0.0468(10) 0.0235(8) 0.0113(7) 0.0175(7)
N2 0.0263(8) 0.0340(9) 0.0339(9) 0.0222(7) 0.0133(7) 0.0201(7)
C1 0.0189(8) 0.0200(8) 0.0225(8) 0.0105(7) 0.0044(7) 0.0096(7)
C2 0.0186(8) 0.0225(8) 0.0234(8) 0.0110(7) 0.0048(7) 0.0121(7)
C3 0.0191(8) 0.0227(8) 0.0216(8) 0.0092(7) 0.0020(7) 0.0114(7)
C4 0.0218(9) 0.0228(8) 0.0219(8) 0.0089(7) 0.0014(7) 0.0123(7)
C5 0.0180(8) 0.0209(8) 0.0209(8) 0.0067(7) 0.0005(6) 0.0099(7)
C6 0.0291(10) 0.0385(11) 0.0246(9) 0.0149(8) 0.0097(8) 0.0218(9)
C7 0.0355(11) 0.0352(10) 0.0242(9) 0.0076(8) 0.0055(8) 0.0260(9)
C8 0.0306(10) 0.0231(9) 0.0296(10) 0.0072(8) -0.0003(8) 0.0163(8)
C9 0.0205(9) 0.0205(8) 0.0277(9) 0.0090(7) 0.0002(7) 0.0097(7)
C10 0.0215(9) 0.0213(8) 0.0282(9) 0.0138(7) 0.0052(7) 0.0087(7)
C11 0.0238(9) 0.0216(8) 0.0194(8) 0.0071(7) 0.0043(7) 0.0121(7)
C12 0.0279(10) 0.0226(9) 0.0306(10) 0.0115(8) 0.0074(8) 0.0105(8)
C13 0.0375(11) 0.0238(9) 0.0345(10) 0.0112(8) 0.0065(9) 0.0174(8)
C14 0.0330(10) 0.0302(10) 0.0229(9) 0.0060(8) 0.0035(8) 0.0205(8)
C15 0.0270(10) 0.0346(10) 0.0283(10) 0.0127(8) 0.0098(8) 0.0168(8)
C16 0.0298(10) 0.0260(9) 0.0272(9) 0.0129(8) 0.0092(8) 0.0151(8)
C17 0.0434(12) 0.0426(12) 0.0363(11) 0.0123(9) 0.0098(9) 0.0310(10)
C18 0.0235(9) 0.0239(8) 0.0220(8) 0.0097(7) 0.0069(7) 0.0154(7)
C19 0.0254(9) 0.0253(9) 0.0265(9) 0.0085(8) 0.0031(7) 0.0127(8)
C20 0.0365(11) 0.0351(10) 0.0220(9) 0.0083(8) 0.0001(8) 0.0208(9)
C21 0.0432(11) 0.0333(10) 0.0240(9) 0.0138(8) 0.0099(8) 0.0261(9)
C22 0.0343(10) 0.0250(9) 0.0302(10) 0.0146(8) 0.0094(8) 0.0150(8)
C23 0.0251(9) 0.0236(9) 0.0249(9) 0.0095(7) 0.0030(7) 0.0115(7)
C24 0.0669(16) 0.0511(14) 0.0358(12) 0.0264(11) 0.0095(11) 0.0338(12)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C11 112.15(8) . . ?
O1 P1 C18 112.09(8) . . ?
C11 P1 C18 106.14(8) . . ?
O1 P1 C1 112.55(7) . . ?
C11 P1 C1 103.88(8) . . ?
C18 P1 C1 109.54(8) . . ?
C3 O2 C4 117.74(13) . . ?
C3 N2 H2B 119.0(14) . . ?
C3 N2 H2A 117.1(13) . . ?
H2B N2 H2A 120.9(19) . . ?
C5 C1 C2 108.48(13) . . ?
C5 C1 P1 111.73(11) . . ?
C2 C1 P1 108.46(11) . . ?
C5 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
P1 C1 H1 109.4 . . ?
C3 C2 C10 118.51(15) . . ?
C3 C2 C1 119.82(14) . . ?
C10 C2 C1 121.35(14) . . ?
N2 C3 O2 111.73(15) . . ?
N2 C3 C2 127.55(15) . . ?
O2 C3 C2 120.70(14) . . ?
C6 C4 C5 121.86(16) . . ?
C6 C4 O2 116.22(15) . . ?
C5 C4 O2 121.92(14) . . ?
C4 C5 C9 117.87(15) . . ?
C4 C5 C1 118.44(14) . . ?
C9 C5 C1 123.69(15) . . ?
C4 C6 C7 119.15(17) . . ?
C4 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.30(17) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.91(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C5 120.87(17) . . ?
C8 C9 H9 119.6 . . ?
C5 C9 H9 119.6 . . ?
N1 C10 C2 178.3(2) . . ?
C16 C11 C12 119.17(15) . . ?
C16 C11 P1 122.85(13) . . ?
C12 C11 P1 117.83(13) . . ?
C13 C12 C11 120.15(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 121.00(17) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 118.57(16) . . ?
C13 C14 C17 121.38(17) . . ?
C15 C14 C17 120.04(18) . . ?
C14 C15 C16 120.98(17) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 120.12(16) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.75(16) . . ?
C23 C18 P1 124.85(13) . . ?
C19 C18 P1 116.16(13) . . ?
C20 C19 C18 120.28(17) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.28(17) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 118.16(17) . . ?
C20 C21 C24 120.22(18) . . ?
C22 C21 C24 121.58(19) . . ?
C21 C22 C23 121.31(17) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 120.17(17) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4876(13) . ?
P1 C11 1.7983(17) . ?
P1 C18 1.8040(17) . ?
P1 C1 1.8472(17) . ?
O2 C3 1.3650(19) . ?
O2 C4 1.395(2) . ?
N1 C10 1.152(2) . ?
N2 C3 1.325(2) . ?
N2 H2B 0.85(2) . ?
N2 H2A 0.92(2) . ?
C1 C5 1.508(2) . ?
C1 C2 1.519(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.372(2) . ?
C2 C10 1.418(2) . ?
C4 C6 1.382(2) . ?
C4 C5 1.388(2) . ?
C5 C9 1.395(2) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C16 1.390(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 C17 1.511(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.392(2) . ?
C18 C19 1.398(2) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(3) . ?
C21 C24 1.514(3) . ?
C22 C23 1.389(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2B N1 0.85(2) 2.23(2) 3.065(2) 167.6(19) 2_666 yes
N2 H2A O1 0.92(2) 1.89(2) 2.811(2) 177.2(19) 2_766 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C5 50.81(13) . . . . ?
C11 P1 C1 C5 172.35(11) . . . . ?
C18 P1 C1 C5 -74.60(13) . . . . ?
O1 P1 C1 C2 -68.71(13) . . . . ?
C11 P1 C1 C2 52.82(13) . . . . ?
C18 P1 C1 C2 165.88(11) . . . . ?
C5 C1 C2 C3 -36.3(2) . . . . ?
P1 C1 C2 C3 85.21(17) . . . . ?
C5 C1 C2 C10 150.28(16) . . . . ?
P1 C1 C2 C10 -88.17(17) . . . . ?
C4 O2 C3 N2 -162.14(14) . . . . ?
C4 O2 C3 C2 16.5(2) . . . . ?
C10 C2 C3 N2 7.3(3) . . . . ?
C1 C2 C3 N2 -166.23(16) . . . . ?
C10 C2 C3 O2 -171.09(15) . . . . ?
C1 C2 C3 O2 15.3(2) . . . . ?
C3 O2 C4 C6 155.89(15) . . . . ?
C3 O2 C4 C5 -24.6(2) . . . . ?
C6 C4 C5 C9 -1.7(3) . . . . ?
O2 C4 C5 C9 178.82(15) . . . . ?
C6 C4 C5 C1 179.35(15) . . . . ?
O2 C4 C5 C1 -0.1(2) . . . . ?
C2 C1 C5 C4 28.2(2) . . . . ?
P1 C1 C5 C4 -91.32(16) . . . . ?
C2 C1 C5 C9 -150.69(16) . . . . ?
P1 C1 C5 C9 89.79(17) . . . . ?
C5 C4 C6 C7 2.4(3) . . . . ?
O2 C4 C6 C7 -178.08(16) . . . . ?
C4 C6 C7 C8 -1.0(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C5 1.7(3) . . . . ?
C4 C5 C9 C8 -0.4(2) . . . . ?
C1 C5 C9 C8 178.50(15) . . . . ?
O1 P1 C11 C16 -157.36(14) . . . . ?
C18 P1 C11 C16 -34.65(17) . . . . ?
C1 P1 C11 C16 80.83(16) . . . . ?
O1 P1 C11 C12 27.16(16) . . . . ?
C18 P1 C11 C12 149.88(14) . . . . ?
C1 P1 C11 C12 -94.64(15) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
P1 C11 C12 C13 176.42(14) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C12 C13 C14 C17 178.21(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C17 C14 C15 C16 -178.62(17) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
P1 C11 C16 C15 -176.57(14) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
O1 P1 C18 C23 -158.94(14) . . . . ?
C11 P1 C18 C23 78.31(16) . . . . ?
C1 P1 C18 C23 -33.26(17) . . . . ?
O1 P1 C18 C19 26.82(15) . . . . ?
C11 P1 C18 C19 -95.93(14) . . . . ?
C1 P1 C18 C19 152.50(13) . . . . ?
C23 C18 C19 C20 -1.7(2) . . . . ?
P1 C18 C19 C20 172.95(13) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 1.6(3) . . . . ?
C19 C20 C21 C24 -176.23(17) . . . . ?
C20 C21 C22 C23 -2.4(3) . . . . ?
C24 C21 C22 C23 175.39(17) . . . . ?
C21 C22 C23 C18 1.2(3) . . . . ?
C19 C18 C23 C22 0.9(2) . . . . ?
P1 C18 C23 C22 -173.23(13) . . . . ?