# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H16 N3 O1 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C10 H16 N3 O1 P1'
_chemical_formula_weight         225.2
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
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
_cell_length_a                   8.9605(2)
_cell_length_b                   10.9173(3)
_cell_length_c                   12.2318(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.135(2)
_cell_angle_gamma                90
_cell_volume                     1169.83(5)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    13501
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.85
_cell_measurement_temperature    120.00(14)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.2784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             480

_exptl_absorpt_coefficient_mu    0.214
_exptl_crystal_description       tabular
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.074
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_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_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            29002
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_full        27.42
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
Following the common practice, the H atoms bonded to C atoms
were kept in ideal positions with distance C--H = 0.96 Å.
Whereas, positions of the H atoms bonded to N atoms were refined
with distance restrictions d(N--H) = 0.87 Å.

Anisotropic ADP of all non-H atoms were refined, while for H atoms Uiso(H)
was set to 1.2Ueq(C,N).
;

_reflns_number_total             2658
_reflns_number_gt                2196
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0404
_refine_ls_R_factor_all          0.0452
_refine_ls_wR_factor_ref         0.0411
_refine_ls_goodness_of_fit_ref   2.15
_refine_ls_goodness_of_fit_gt    2.33
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     145
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0128
_refine_ls_shift/su_mean         0.0013
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.1023 0.0942 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.68485(4) 0.14339(3) 0.48374(3) Uani 0.01294(12) 4 1 d . . .
O1 O 0.51827(10) 0.14718(8) 0.43651(8) Uani 0.0175(3) 4 1 d . . .
N1 N 0.74550(13) 0.23893(10) 0.58639(10) Uani 0.0167(4) 4 1 d . . .
N2 N 0.78309(12) 0.17852(10) 0.38818(10) Uani 0.0147(4) 4 1 d . . .
N3 N 0.73365(12) 0.00597(10) 0.53318(9) Uani 0.0139(4) 4 1 d . . .
C1 C 0.64704(17) -0.00342(14) 0.13085(12) Uani 0.0235(5) 4 1 d . . .
C2 C 0.84243(16) 0.13554(13) 0.10084(12) Uani 0.0206(5) 4 1 d . . .
C3 C 0.73873(16) 0.04275(13) 0.06237(12) Uani 0.0232(5) 4 1 d . . .
C4 C 0.87747(16) 0.08031(13) 0.71658(12) Uani 0.0229(5) 4 1 d . . .
C5 C 0.94402(19) 0.18663(16) 0.02798(13) Uani 0.0340(6) 4 1 d . . .
C6 C 0.65865(15) 0.04001(13) 0.23905(12) Uani 0.0192(5) 4 1 d . . .
C7 C 0.76292(14) 0.13210(12) 0.27888(11) Uani 0.0147(4) 4 1 d . . .
C8 C 0.85293(15) 0.18006(13) 0.20837(11) Uani 0.0167(4) 4 1 d . . .
C9 C 0.87546(17) 0.21284(13) 0.67992(12) Uani 0.0222(5) 4 1 d . . .
C10 C 0.87458(16) -0.00663(13) 0.61996(11) Uani 0.0185(4) 4 1 d . . .
H1c1 H 0.574256 -0.066474 0.103037 Uiso 0.0282 4 1 d . . .
H1c3 H 0.730545 0.010557 -0.01169 Uiso 0.0279 4 1 d . . .
H1c4 H 0.967211 0.065334 0.773421 Uiso 0.0275 4 1 d . . .
H2c4 H 0.791034 0.064707 0.749461 Uiso 0.0275 4 1 d . . .
H1c5 H 1.004928 0.251885 0.066765 Uiso 0.0408 4 1 d . . .
H2c5 H 1.009601 0.123043 0.010998 Uiso 0.0408 4 1 d . . .
H3c5 H 0.882203 0.217472 -0.040209 Uiso 0.0408 4 1 d . . .
H1c6 H 0.595168 0.006662 0.285909 Uiso 0.023 4 1 d . . .
H1c8 H 0.923331 0.245078 0.235017 Uiso 0.02 4 1 d . . .
H1c9 H 0.869769 0.265133 0.742003 Uiso 0.0267 4 1 d . . .
H2c9 H 0.969359 0.231755 0.657598 Uiso 0.0267 4 1 d . . .
H1c10 H 0.961556 0.008439 0.58754 Uiso 0.0222 4 1 d . . .
H2c10 H 0.88351 -0.08936 0.647147 Uiso 0.0222 4 1 d . . .
H1n1 H 0.7356(16) 0.3154(4) 0.5663(12) Uiso 0.0201 4 1 d . . .
H1n2 H 0.8589(11) 0.2292(10) 0.4078(11) Uiso 0.0176 4 1 d . . .
H1n3 H 0.6563(10) -0.0319(12) 0.5503(12) Uiso 0.0167 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . . 1.4836(9) ?
P1 N1 . . 1.6349(12) ?
P1 N2 . . 1.6495(13) ?
P1 N3 . . 1.6422(11) ?
N1 C9 . . 1.4785(17) ?
N1 H1n1 . . 0.870(6) ?
N2 C7 . . 1.4054(18) ?
N2 H1n2 . . 0.870(10) ?
N3 C10 . . 1.4754(16) ?
N3 H1n3 . . 0.870(12) ?
C1 C3 . . 1.386(2) ?
C1 C6 . . 1.389(2) ?
C1 H1c1 . . 0.96 ?
C2 C3 . . 1.388(2) ?
C2 C5 . . 1.508(2) ?
C2 C8 . . 1.387(2) ?
C3 H1c3 . . 0.96 ?
C4 C9 . . 1.514(2) ?
C4 C10 . . 1.512(2) ?
C4 H1c4 . . 0.96 ?
C4 H2c4 . . 0.96 ?
C5 H1c5 . . 0.96 ?
C5 H2c5 . . 0.96 ?
C5 H3c5 . . 0.96 ?
C6 C7 . . 1.3892(19) ?
C6 H1c6 . . 0.96 ?
C7 C8 . . 1.400(2) ?
C8 H1c8 . . 0.96 ?
C9 H1c9 . . 0.96 ?
C9 H2c9 . . 0.96 ?
C10 H1c10 . . 0.96 ?
C10 H2c10 . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N1 . . . 115.22(6) ?
O1 P1 N2 . . . 111.14(6) ?
O1 P1 N3 . . . 109.70(5) ?
N1 P1 N2 . . . 104.78(6) ?
N1 P1 N3 . . . 106.27(6) ?
N2 P1 N3 . . . 109.45(6) ?
P1 N1 C9 . . . 123.50(9) ?
P1 N1 H1n1 . . . 113.4(9) ?
C9 N1 H1n1 . . . 114.9(8) ?
P1 N2 C7 . . . 127.53(9) ?
P1 N2 H1n2 . . . 117.0(9) ?
C7 N2 H1n2 . . . 115.4(9) ?
P1 N3 C10 . . . 118.13(9) ?
P1 N3 H1n3 . . . 111.0(8) ?
C10 N3 H1n3 . . . 112.8(8) ?
C3 C1 C6 . . . 121.11(13) ?
C3 C1 H1c1 . . . 119.45 ?
C6 C1 H1c1 . . . 119.45 ?
C3 C2 C5 . . . 120.90(14) ?
C3 C2 C8 . . . 118.97(14) ?
C5 C2 C8 . . . 120.12(13) ?
C1 C3 C2 . . . 120.01(14) ?
C1 C3 H1c3 . . . 119.99 ?
C2 C3 H1c3 . . . 119.99 ?
C9 C4 C10 . . . 111.79(12) ?
C9 C4 H1c4 . . . 109.47 ?
C9 C4 H2c4 . . . 109.47 ?
C10 C4 H1c4 . . . 109.47 ?
C10 C4 H2c4 . . . 109.47 ?
H1c4 C4 H2c4 . . . 107.05 ?
C2 C5 H1c5 . . . 109.47 ?
C2 C5 H2c5 . . . 109.47 ?
C2 C5 H3c5 . . . 109.47 ?
H1c5 C5 H2c5 . . . 109.47 ?
H1c5 C5 H3c5 . . . 109.47 ?
H2c5 C5 H3c5 . . . 109.47 ?
C1 C6 C7 . . . 119.43(14) ?
C1 C6 H1c6 . . . 120.29 ?
C7 C6 H1c6 . . . 120.29 ?
N2 C7 C6 . . . 122.49(13) ?
N2 C7 C8 . . . 118.39(11) ?
C6 C7 C8 . . . 119.12(13) ?
C2 C8 C7 . . . 121.34(12) ?
C2 C8 H1c8 . . . 119.33 ?
C7 C8 H1c8 . . . 119.33 ?
N1 C9 C4 . . . 111.83(11) ?
N1 C9 H1c9 . . . 109.47 ?
N1 C9 H2c9 . . . 109.47 ?
C4 C9 H1c9 . . . 109.47 ?
C4 C9 H2c9 . . . 109.47 ?
H1c9 C9 H2c9 . . . 107.01 ?
N3 C10 C4 . . . 112.04(11) ?
N3 C10 H1c10 . . . 109.47 ?
N3 C10 H2c10 . . . 109.47 ?
C4 C10 H1c10 . . . 109.47 ?
C4 C10 H2c10 . . . 109.47 ?
H1c10 C10 H2c10 . . . 106.77 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1n1 N3 . . 2_656 0.870(6) 2.454(9) 3.2845(16) 159.8(14) ?
N2 H1n2 O1 . . 4_555 0.870(10) 1.943(10) 2.8084(14) 173.5(12) ?
N3 H1n3 O1 . . 3_656 0.870(12) 2.040(11) 2.8948(15) 167.2(13) ?


#=======================================================================
_database_code_depnum_ccdc_archive 'CCDC 960999'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H20 N3 O1 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H20 N3 O1 P1'
_chemical_formula_weight         253.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
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
_cell_length_a                   9.3055(3)
_cell_length_b                   10.8856(3)
_cell_length_c                   12.9523(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.386(2)
_cell_angle_gamma                90
_cell_volume                     1309.73(7)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    10695
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      66.97
_cell_measurement_temperature    120.00(14)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.2841
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    1.77
_exptl_crystal_description       blocky
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.268
_exptl_crystal_size_min          0.229
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_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_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            21603
_diffrn_reflns_theta_min         5.31
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_full        67.08
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.99
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
The ring of the molecule presents some disorder.
It is modeled through a rigid body (which includes also the CH3 group) 
located at two slightly different positions with different orientations. 
Each position has a different occupancy factor 
and the total occupancy is restricted to be one.

Following the common practice, H atoms bonded to C atoms
were kept in ideal positions with C--H = 0.96 Å.
On the other hand, positions of the H atoms bonded to N atoms were refined
with distance restrictions d(N--H)=0.87 Å.

Anisotropic ADP of all non-H atoms were refined, while for H atoms Uiso(H)
was set to 1.2Ueq(C,N).
;

_reflns_number_total             2327
_reflns_number_gt                2029
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0383
_refine_ls_R_factor_all          0.0361
_refine_ls_wR_factor_ref         0.0391
_refine_ls_goodness_of_fit_ref   2.19
_refine_ls_goodness_of_fit_gt    2.31
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         2327
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0180
_refine_ls_shift/su_mean         0.0011
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

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'

_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_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
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_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
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_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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
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_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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
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 ?

#=======================================================================
_database_code_depnum_ccdc_archive 'CCDC 961000'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H26 N3 O1 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C22 H26 N3 O1 P1'
_chemical_formula_weight         379.4
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P -2xab;-2ybc;-2zac'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z+1/2
8 -x+1/2,y+1/2,z
_cell_length_a                   10.5318(3)
_cell_length_b                   9.1502(3)
_cell_length_c                   40.9969(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3950.8(2)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            8

_cell_measurement_reflns_used    12972
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      67.03
_cell_measurement_temperature    120.00(10)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.2754
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1616

_exptl_absorpt_coefficient_mu    1.356
_exptl_crystal_description       blocky
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.134
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.309
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            24540
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_full        67.01
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.99
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
The H atoms could be located in the corresponding difference Fourier map,
but, according to the usual practice, the positions of the H atoms
connected to C atoms were kept with ideal geometry at distance d(C--H) = 0.96 Å.
The position of the H atom bonded to the N atom was refined
with a distance restriction d(N--H) = 0.87 Å.

Anisotropic ADP were refined for all non-H atoms.
For H atoms, Uiso(H) was set to 1.2Ueq(C, N).
;

_reflns_number_total             3499
_reflns_number_gt                2851
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_gt          0.0390
_refine_ls_R_factor_all          0.0426
_refine_ls_wR_factor_ref         0.0399
_refine_ls_goodness_of_fit_ref   1.93
_refine_ls_goodness_of_fit_gt    2.11
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3499
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0283
_refine_ls_shift/su_mean         0.0013
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

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'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12349(3) 0.14454(4) 0.142510(9) Uani 0.01866(11) 8 1 d . . .
O1 O 0.14310(10) 0.30348(11) 0.13790(3) Uani 0.0229(3) 8 1 d . . .
N1 N 0.23986(12) 0.06479(13) 0.16296(3) Uani 0.0216(4) 8 1 d . . .
N2 N -0.00837(11) 0.11175(13) 0.16294(3) Uani 0.0220(4) 8 1 d . . .
N3 N 0.11775(12) 0.05821(13) 0.10738(3) Uani 0.0224(4) 8 1 d . . .
C1 C 0.29721(13) 0.11881(16) 0.19157(4) Uani 0.0195(4) 8 1 d . . .
C2 C 0.24057(14) 0.22791(17) 0.21034(4) Uani 0.0231(4) 8 1 d . . .
C3 C 0.41455(14) 0.06325(16) 0.20146(4) Uani 0.0216(4) 8 1 d . . .
C4 C 0.21622(15) 0.08699(18) 0.08287(4) Uani 0.0283(5) 8 1 d . . .
C5 C 0.07736(16) 0.25618(18) 0.05055(4) Uani 0.0292(5) 8 1 d . . .
C6 C 0.41824(16) 0.22785(18) 0.24722(4) Uani 0.0276(5) 8 1 d . . .
C7 C -0.39831(17) 0.08972(18) 0.08878(4) Uani 0.0326(5) 8 1 d . . .
C8 C -0.21639(14) 0.16638(16) 0.13513(4) Uani 0.0227(4) 8 1 d . . .
C9 C 0.30103(15) 0.28198(18) 0.23780(4) Uani 0.0268(5) 8 1 d . . .
C10 C -0.03506(15) -0.02674(17) 0.17946(4) Uani 0.0274(5) 8 1 d . . .
C11 C 0.47422(15) 0.11782(17) 0.22898(4) Uani 0.0258(5) 8 1 d . . .
C12 C 0.01947(18) 0.30109(20) 0.02198(4) Uani 0.0358(6) 8 1 d . . .
C13 C -0.11763(14) 0.21131(17) 0.16002(4) Uani 0.0252(5) 8 1 d . . .
C14 C 0.15975(15) 0.13756(18) 0.05089(4) Uani 0.0272(5) 8 1 d . . .
C15 C -0.28269(17) 0.1457(2) 0.07904(4) Uani 0.0379(6) 8 1 d . . .
C16 C 0.04639(16) -0.07639(17) 0.10225(4) Uani 0.0313(5) 8 1 d . . .
C17 C 0.0458(2) 0.2290(2) -0.00697(5) Uani 0.0444(7) 8 1 d . . .
C18 C -0.42383(17) 0.07307(19) 0.12153(5) Uani 0.0356(5) 8 1 d . . .
C19 C -0.33291(15) 0.11148(18) 0.14444(4) Uani 0.0286(5) 8 1 d . . .
C20 C -0.19302(16) 0.1844(2) 0.10211(4) Uani 0.0365(6) 8 1 d . . .
C21 C 0.18604(18) 0.0671(2) 0.02165(4) Uani 0.0384(6) 8 1 d . . .
C22 C 0.1297(2) 0.1134(2) -0.00709(5) Uani 0.0498(7) 8 1 d . . .
H1c2 H 0.159034 0.265835 0.204175 Uiso 0.0277 8 1 d . . .
H1c3 H 0.45413 -0.013306 0.189086 Uiso 0.0259 8 1 d . . .
H1c4 H 0.265061 -0.000151 0.079324 Uiso 0.034 8 1 d . . .
H2c4 H 0.273562 0.160079 0.090951 Uiso 0.034 8 1 d . . .
H1c5 H 0.060356 0.307761 0.070469 Uiso 0.0351 8 1 d . . .
H1c6 H 0.460223 0.266121 0.266171 Uiso 0.0332 8 1 d . . .
H1c7 H -0.460655 0.062509 0.07281 Uiso 0.0391 8 1 d . . .
H1c9 H 0.261347 0.357639 0.250424 Uiso 0.0322 8 1 d . . .
H1c10 H 0.04058 -0.085243 0.179973 Uiso 0.0329 8 1 d . . .
H2c10 H -0.062746 -0.007631 0.201364 Uiso 0.0329 8 1 d . . .
H3c10 H -0.100515 -0.078153 0.167893 Uiso 0.0329 8 1 d . . .
H1c11 H 0.555058 0.079087 0.235489 Uiso 0.031 8 1 d . . .
H1c12 H -0.038678 0.381872 0.022201 Uiso 0.043 8 1 d . . .
H1c13 H -0.087982 0.308074 0.155139 Uiso 0.0302 8 1 d . . .
H2c13 H -0.157242 0.222571 0.180962 Uiso 0.0302 8 1 d . . .
H1c15 H -0.264532 0.157832 0.056252 Uiso 0.0454 8 1 d . . .
H1c16 H -0.032661 -0.071148 0.113854 Uiso 0.0375 8 1 d . . .
H2c16 H 0.029956 -0.08876 0.079386 Uiso 0.0375 8 1 d . . .
H3c16 H 0.094885 -0.157893 0.110142 Uiso 0.0375 8 1 d . . .
H1c17 H 0.005649 0.259448 -0.026867 Uiso 0.0533 8 1 d . . .
H1c18 H -0.504344 0.034965 0.128473 Uiso 0.0427 8 1 d . . .
H1c19 H -0.351391 0.099653 0.167215 Uiso 0.0343 8 1 d . . .
H1c20 H -0.113222 0.2243 0.095132 Uiso 0.0438 8 1 d . . .
H1c21 H 0.243639 -0.01418 0.021349 Uiso 0.0461 8 1 d . . .
H1c22 H 0.149262 0.064646 -0.027212 Uiso 0.0598 8 1 d . . .
H1n1 H 0.2748(15) -0.0145(11) 0.1555(4) Uiso 0.0259 8 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . . 1.4811(11) ?
P1 N1 . . 1.6544(13) ?
P1 N2 . . 1.6493(13) ?
P1 N3 . . 1.6436(13) ?
N1 C1 . . 1.4091(19) ?
N1 H1n1 . . 0.870(12) ?
N2 C10 . . 1.464(2) ?
N2 C13 . . 1.4725(19) ?
N3 C4 . . 1.468(2) ?
N3 C16 . . 1.458(2) ?
C1 C2 . . 1.394(2) ?
C1 C3 . . 1.396(2) ?
C2 C9 . . 1.385(2) ?
C2 H1c2 . . 0.96 ?
C3 C11 . . 1.385(2) ?
C3 H1c3 . . 0.96 ?
C4 C14 . . 1.512(2) ?
C4 H1c4 . . 0.96 ?
C4 H2c4 . . 0.96 ?
C5 C12 . . 1.383(2) ?
C5 C14 . . 1.390(2) ?
C5 H1c5 . . 0.96 ?
C6 C9 . . 1.385(2) ?
C6 C11 . . 1.386(2) ?
C6 H1c6 . . 0.96 ?
C7 C15 . . 1.380(2) ?
C7 C18 . . 1.378(3) ?
C7 H1c7 . . 0.96 ?
C8 C13 . . 1.514(2) ?
C8 C19 . . 1.380(2) ?
C8 C20 . . 1.386(2) ?
C9 H1c9 . . 0.96 ?
C10 H1c10 . . 0.96 ?
C10 H2c10 . . 0.96 ?
C10 H3c10 . . 0.96 ?
C11 H1c11 . . 0.96 ?
C12 C17 . . 1.386(3) ?
C12 H1c12 . . 0.96 ?
C13 H1c13 . . 0.96 ?
C13 H2c13 . . 0.96 ?
C14 C21 . . 1.389(2) ?
C15 C20 . . 1.382(2) ?
C15 H1c15 . . 0.96 ?
C16 H1c16 . . 0.96 ?
C16 H2c16 . . 0.96 ?
C16 H3c16 . . 0.96 ?
C17 C22 . . 1.379(3) ?
C17 H1c17 . . 0.96 ?
C18 C19 . . 1.386(2) ?
C18 H1c18 . . 0.96 ?
C19 H1c19 . . 0.96 ?
C20 H1c20 . . 0.96 ?
C21 C22 . . 1.385(3) ?
C21 H1c21 . . 0.96 ?
C22 H1c22 . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N1 . . . 113.23(6) ?
O1 P1 N2 . . . 111.15(6) ?
O1 P1 N3 . . . 111.42(6) ?
N1 P1 N2 . . . 106.63(6) ?
N1 P1 N3 . . . 105.02(6) ?
N2 P1 N3 . . . 109.07(6) ?
P1 N1 C1 . . . 125.78(10) ?
P1 N1 H1n1 . . . 120.2(11) ?
C1 N1 H1n1 . . . 113.9(11) ?
P1 N2 C10 . . . 123.64(10) ?
P1 N2 C13 . . . 120.28(10) ?
C10 N2 C13 . . . 115.02(12) ?
P1 N3 C4 . . . 119.18(10) ?
P1 N3 C16 . . . 123.45(11) ?
C4 N3 C16 . . . 114.65(12) ?
N1 C1 C2 . . . 121.81(13) ?
N1 C1 C3 . . . 119.56(13) ?
C2 C1 C3 . . . 118.63(13) ?
C1 C2 C9 . . . 120.51(14) ?
C1 C2 H1c2 . . . 119.75 ?
C9 C2 H1c2 . . . 119.75 ?
C1 C3 C11 . . . 120.45(14) ?
C1 C3 H1c3 . . . 119.78 ?
C11 C3 H1c3 . . . 119.77 ?
N3 C4 C14 . . . 111.75(12) ?
N3 C4 H1c4 . . . 109.47 ?
N3 C4 H2c4 . . . 109.47 ?
C14 C4 H1c4 . . . 109.47 ?
C14 C4 H2c4 . . . 109.47 ?
H1c4 C4 H2c4 . . . 107.09 ?
C12 C5 C14 . . . 121.04(16) ?
C12 C5 H1c5 . . . 119.48 ?
C14 C5 H1c5 . . . 119.48 ?
C9 C6 C11 . . . 119.25(15) ?
C9 C6 H1c6 . . . 120.38 ?
C11 C6 H1c6 . . . 120.38 ?
C15 C7 C18 . . . 119.67(16) ?
C15 C7 H1c7 . . . 120.16 ?
C18 C7 H1c7 . . . 120.16 ?
C13 C8 C19 . . . 121.57(14) ?
C13 C8 C20 . . . 120.28(14) ?
C19 C8 C20 . . . 118.11(15) ?
C2 C9 C6 . . . 120.58(15) ?
C2 C9 H1c9 . . . 119.71 ?
C6 C9 H1c9 . . . 119.71 ?
N2 C10 H1c10 . . . 109.47 ?
N2 C10 H2c10 . . . 109.47 ?
N2 C10 H3c10 . . . 109.47 ?
H1c10 C10 H2c10 . . . 109.47 ?
H1c10 C10 H3c10 . . . 109.47 ?
H2c10 C10 H3c10 . . . 109.47 ?
C3 C11 C6 . . . 120.57(14) ?
C3 C11 H1c11 . . . 119.72 ?
C6 C11 H1c11 . . . 119.71 ?
C5 C12 C17 . . . 119.73(17) ?
C5 C12 H1c12 . . . 120.14 ?
C17 C12 H1c12 . . . 120.13 ?
N2 C13 C8 . . . 115.07(13) ?
N2 C13 H1c13 . . . 109.47 ?
N2 C13 H2c13 . . . 109.47 ?
C8 C13 H1c13 . . . 109.47 ?
C8 C13 H2c13 . . . 109.47 ?
H1c13 C13 H2c13 . . . 103.23 ?
C4 C14 C5 . . . 119.54(14) ?
C4 C14 C21 . . . 121.87(15) ?
C5 C14 C21 . . . 118.58(15) ?
C7 C15 C20 . . . 119.99(16) ?
C7 C15 H1c15 . . . 120.01 ?
C20 C15 H1c15 . . . 120.01 ?
N3 C16 H1c16 . . . 109.47 ?
N3 C16 H2c16 . . . 109.47 ?
N3 C16 H3c16 . . . 109.47 ?
H1c16 C16 H2c16 . . . 109.47 ?
H1c16 C16 H3c16 . . . 109.47 ?
H2c16 C16 H3c16 . . . 109.47 ?
C12 C17 C22 . . . 119.77(18) ?
C12 C17 H1c17 . . . 120.12 ?
C22 C17 H1c17 . . . 120.12 ?
C7 C18 C19 . . . 119.83(16) ?
C7 C18 H1c18 . . . 120.09 ?
C19 C18 H1c18 . . . 120.08 ?
C8 C19 C18 . . . 121.28(16) ?
C8 C19 H1c19 . . . 119.36 ?
C18 C19 H1c19 . . . 119.36 ?
C8 C20 C15 . . . 121.10(16) ?
C8 C20 H1c20 . . . 119.45 ?
C15 C20 H1c20 . . . 119.45 ?
C14 C21 C22 . . . 120.46(18) ?
C14 C21 H1c21 . . . 119.77 ?
C22 C21 H1c21 . . . 119.77 ?
C17 C22 C21 . . . 120.39(18) ?
C17 C22 H1c22 . . . 119.81 ?
C21 C22 H1c22 . . . 119.81 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1n1 O1 . . 8_545 0.870(12) 2.010(12) 2.8795(16) 179.4(14) ?


#=======================================================================

_database_code_depnum_ccdc_archive 'CCDC 961001'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H22 N3 O1 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C20 H22 N3 O1 P1'
_chemical_formula_weight         351.4
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_Int_Tables_number      88
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y+1/2,z+1/2
3 -y,x+1/2,z+1/4
4 y+1/2,-x,z+3/4
5 -x,-y+1/2,-z+1/4
6 x+1/2,y,-z+3/4
7 y,-x,-z
8 -y+1/2,x+1/2,-z+1/2
9 x+1/2,y+1/2,z+1/2
10 -x,-y,z
11 -y+1/2,x,z+3/4
12 y,-x+1/2,z+1/4
13 -x+1/2,-y,-z+3/4
14 x,y+1/2,-z+1/4
15 y+1/2,-x+1/2,-z+1/2
16 -y,x,-z
_cell_length_a                   36.2225(16)
_cell_length_b                   36.2225(16)
_cell_length_c                   5.4306(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7125.3(5)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            16

_cell_measurement_reflns_used    1149
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      41.22
_cell_measurement_temperature    120.00(10)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.3098
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2976

_exptl_absorpt_coefficient_mu    1.463
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.101
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            22485
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         67.26
_diffrn_reflns_theta_full        67.26
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
Although they could be located in the corresponding difference Fourier map,
the H atoms bonded to C atoms were kept at their ideal positions
with a distance d(C--H) = 0.96 Å, according to the common practice.
The positions of the H atoms bonded to the N atoms were refined
with a distance restriction d(N--H) = 0.87 Å.

All non-H atoms were described with anisotropic ADP and
for H atoms, Uiso(H) was fixed to 1.2Ueq(C, N).
;

_reflns_number_total             3160
_reflns_number_gt                2389
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_gt          0.0433
_refine_ls_R_factor_all          0.0617
_refine_ls_wR_factor_ref         0.0460
_refine_ls_goodness_of_fit_ref   1.73
_refine_ls_goodness_of_fit_gt    1.90
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3160
_refine_ls_number_parameters     235
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0294
_refine_ls_shift/su_mean         0.0017
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

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'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.003593(14) 0.191835(14) 0.03720(11) Uani 0.02300(17) 16 1 d . . .
O1 O -0.01339(4) 0.20566(4) 0.2686(3) Uani 0.0255(5) 16 1 d . . .
N1 N -0.02571(5) 0.18872(5) -0.1949(3) Uani 0.0246(6) 16 1 d . . .
N2 N 0.02073(5) 0.15026(5) 0.0631(3) Uani 0.0247(6) 16 1 d . . .
N3 N 0.03749(5) 0.21878(5) -0.0444(4) Uani 0.0267(6) 16 1 d . . .
C1 C 0.06831(6) 0.09895(6) 0.5778(4) Uani 0.0283(7) 16 1 d . . .
C2 C 0.11294(6) 0.23899(6) 0.0545(4) Uani 0.0269(7) 16 1 d . . .
C3 C 0.14938(7) 0.24766(6) 0.1086(5) Uani 0.0321(8) 16 1 d . . .
C4 C 0.10424(6) 0.21918(5) -0.1551(4) Uani 0.0221(6) 16 1 d . . .
C5 C -0.13843(6) 0.16031(6) -0.1802(4) Uani 0.0266(7) 16 1 d . . .
C6 C 0.06033(6) 0.07477(6) 0.7671(4) Uani 0.0309(7) 16 1 d . . .
C7 C 0.06510(5) 0.20952(6) -0.2290(4) Uani 0.0253(7) 16 1 d . . .
C8 C -0.06347(5) 0.17823(5) -0.1866(4) Uani 0.0210(6) 16 1 d . . .
C9 C -0.12351(6) 0.17969(6) -0.3759(4) Uani 0.0283(7) 16 1 d . . .
C10 C -0.08640(6) 0.18863(6) -0.3799(4) Uani 0.0252(7) 16 1 d . . .
C11 C -0.11552(6) 0.14987(6) 0.0114(4) Uani 0.0268(7) 16 1 d . . .
C12 C 0.13279(6) 0.20796(6) -0.3089(4) Uani 0.0258(7) 16 1 d . . .
C13 C -0.07820(6) 0.15879(6) 0.0091(4) Uani 0.0257(7) 16 1 d . . .
C14 C 0.05033(6) 0.14168(6) 0.2357(4) Uani 0.0262(7) 16 1 d . . .
C15 C 0.16903(6) 0.21634(6) -0.2551(5) Uani 0.0317(8) 16 1 d . . .
C16 C 0.04032(6) 0.11412(6) 0.4338(4) Uani 0.0239(7) 16 1 d . . .
C17 C 0.17740(6) 0.23615(6) -0.0462(5) Uani 0.0330(8) 16 1 d . . .
C18 C 0.00429(6) 0.10364(6) 0.4808(4) Uani 0.0303(7) 16 1 d . . .
C19 C -0.00374(7) 0.07865(7) 0.6672(4) Uani 0.0338(8) 16 1 d . . .
C20 C 0.02426(7) 0.06435(6) 0.8123(5) Uani 0.0323(8) 16 1 d . . .
H1c1 H 0.093531 0.105409 0.544855 Uiso 0.0339 16 1 d . . .
H1c2 H 0.093619 0.246832 0.163605 Uiso 0.0323 16 1 d . . .
H1c3 H 0.155131 0.261668 0.253661 Uiso 0.0385 16 1 d . . .
H1c5 H -0.164216 0.154211 -0.177386 Uiso 0.032 16 1 d . . .
H1c6 H 0.079908 0.065166 0.867628 Uiso 0.037 16 1 d . . .
H1c7 H 0.059131 0.221608 -0.381166 Uiso 0.0304 16 1 d . . .
H2c7 H 0.06363 0.183665 -0.266516 Uiso 0.0304 16 1 d . . .
H1c9 H -0.139084 0.18701 -0.510292 Uiso 0.034 16 1 d . . .
H1c10 H -0.076411 0.202079 -0.516889 Uiso 0.0302 16 1 d . . .
H1c11 H -0.125526 0.136287 0.147746 Uiso 0.0321 16 1 d . . .
H1c12 H 0.127183 0.194126 -0.454949 Uiso 0.031 16 1 d . . .
H1c13 H -0.062649 0.151445 0.14355 Uiso 0.0309 16 1 d . . .
H1c14 H 0.058981 0.164053 0.310891 Uiso 0.0314 16 1 d . . .
H2c14 H 0.071498 0.132971 0.146618 Uiso 0.0314 16 1 d . . .
H1c15 H 0.188414 0.208378 -0.363374 Uiso 0.038 16 1 d . . .
H1c17 H 0.202616 0.241951 -0.008016 Uiso 0.0397 16 1 d . . .
H1c18 H -0.015388 0.113746 0.383447 Uiso 0.0363 16 1 d . . .
H1c19 H -0.028829 0.071251 0.695599 Uiso 0.0406 16 1 d . . .
H1c20 H 0.018666 0.047384 0.942832 Uiso 0.0388 16 1 d . . .
H1n1 H -0.0186(6) 0.1958(6) -0.3407(18) Uiso 0.0295 16 1 d . . .
H1n2 H 0.0160(6) 0.1347(5) -0.055(3) Uiso 0.0296 16 1 d . . .
H1n3 H 0.0325(6) 0.24220(15) -0.032(4) Uiso 0.0321 16 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . . 1.4859(15) ?
P1 N1 . . 1.6518(18) ?
P1 N2 . . 1.6347(18) ?
P1 N3 . . 1.6301(18) ?
N1 C8 . . 1.420(3) ?
N1 H1n1 . . 0.870(13) ?
N2 C14 . . 1.458(3) ?
N2 H1n2 . . 0.870(16) ?
N3 C7 . . 1.455(3) ?
N3 H1n3 . . 0.870(7) ?
C1 C6 . . 1.381(3) ?
C1 C16 . . 1.393(3) ?
C1 H1c1 . . 0.96 ?
C2 C3 . . 1.388(3) ?
C2 C4 . . 1.382(3) ?
C2 H1c2 . . 0.96 ?
C3 C17 . . 1.382(3) ?
C3 H1c3 . . 0.96 ?
C4 C7 . . 1.514(3) ?
C4 C12 . . 1.390(3) ?
C5 C9 . . 1.384(3) ?
C5 C11 . . 1.384(3) ?
C5 H1c5 . . 0.96 ?
C6 C20 . . 1.382(3) ?
C6 H1c6 . . 0.96 ?
C7 H1c7 . . 0.96 ?
C7 H2c7 . . 0.96 ?
C8 C10 . . 1.391(3) ?
C8 C13 . . 1.382(3) ?
C9 C10 . . 1.383(3) ?
C9 H1c9 . . 0.96 ?
C10 H1c10 . . 0.96 ?
C11 C13 . . 1.390(3) ?
C11 H1c11 . . 0.96 ?
C12 C15 . . 1.379(3) ?
C12 H1c12 . . 0.96 ?
C13 H1c13 . . 0.96 ?
C14 C16 . . 1.511(3) ?
C14 H1c14 . . 0.96 ?
C14 H2c14 . . 0.96 ?
C15 C17 . . 1.376(3) ?
C15 H1c15 . . 0.96 ?
C16 C18 . . 1.383(3) ?
C17 H1c17 . . 0.96 ?
C18 C19 . . 1.389(3) ?
C18 H1c18 . . 0.96 ?
C19 C20 . . 1.385(3) ?
C19 H1c19 . . 0.96 ?
C20 H1c20 . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N1 . . . 113.72(9) ?
O1 P1 N2 . . . 113.26(9) ?
O1 P1 N3 . . . 109.87(9) ?
N1 P1 N2 . . . 104.28(9) ?
N1 P1 N3 . . . 108.51(10) ?
N2 P1 N3 . . . 106.80(9) ?
P1 N1 C8 . . . 127.78(15) ?
P1 N1 H1n1 . . . 119.0(13) ?
C8 N1 H1n1 . . . 113.0(13) ?
P1 N2 C14 . . . 122.08(14) ?
P1 N2 H1n2 . . . 117.3(12) ?
C14 N2 H1n2 . . . 118.7(13) ?
P1 N3 C7 . . . 124.53(14) ?
P1 N3 H1n3 . . . 114.0(14) ?
C7 N3 H1n3 . . . 115.0(15) ?
C6 C1 C16 . . . 121.1(2) ?
C6 C1 H1c1 . . . 119.47 ?
C16 C1 H1c1 . . . 119.47 ?
C3 C2 C4 . . . 120.6(2) ?
C3 C2 H1c2 . . . 119.72 ?
C4 C2 H1c2 . . . 119.72 ?
C2 C3 C17 . . . 120.1(2) ?
C2 C3 H1c3 . . . 119.96 ?
C17 C3 H1c3 . . . 119.96 ?
C2 C4 C7 . . . 123.47(19) ?
C2 C4 C12 . . . 118.48(19) ?
C7 C4 C12 . . . 118.05(19) ?
C9 C5 C11 . . . 118.8(2) ?
C9 C5 H1c5 . . . 120.59 ?
C11 C5 H1c5 . . . 120.59 ?
C1 C6 C20 . . . 120.2(2) ?
C1 C6 H1c6 . . . 119.91 ?
C20 C6 H1c6 . . . 119.91 ?
N3 C7 C4 . . . 114.07(18) ?
N3 C7 H1c7 . . . 109.47 ?
N3 C7 H2c7 . . . 109.47 ?
C4 C7 H1c7 . . . 109.47 ?
C4 C7 H2c7 . . . 109.47 ?
H1c7 C7 H2c7 . . . 104.45 ?
N1 C8 C10 . . . 118.59(18) ?
N1 C8 C13 . . . 122.20(19) ?
C10 C8 C13 . . . 119.19(18) ?
C5 C9 C10 . . . 120.7(2) ?
C5 C9 H1c9 . . . 119.64 ?
C10 C9 H1c9 . . . 119.65 ?
C8 C10 C9 . . . 120.3(2) ?
C8 C10 H1c10 . . . 119.83 ?
C9 C10 H1c10 . . . 119.83 ?
C5 C11 C13 . . . 120.9(2) ?
C5 C11 H1c11 . . . 119.57 ?
C13 C11 H1c11 . . . 119.57 ?
C4 C12 C15 . . . 121.1(2) ?
C4 C12 H1c12 . . . 119.43 ?
C15 C12 H1c12 . . . 119.43 ?
C8 C13 C11 . . . 120.1(2) ?
C8 C13 H1c13 . . . 119.96 ?
C11 C13 H1c13 . . . 119.96 ?
N2 C14 C16 . . . 114.96(17) ?
N2 C14 H1c14 . . . 109.47 ?
N2 C14 H2c14 . . . 109.47 ?
C16 C14 H1c14 . . . 109.47 ?
C16 C14 H2c14 . . . 109.47 ?
H1c14 C14 H2c14 . . . 103.36 ?
C12 C15 C17 . . . 119.9(2) ?
C12 C15 H1c15 . . . 120.04 ?
C17 C15 H1c15 . . . 120.03 ?
C1 C16 C14 . . . 119.04(18) ?
C1 C16 C18 . . . 118.3(2) ?
C14 C16 C18 . . . 122.61(19) ?
C3 C17 C15 . . . 119.8(2) ?
C3 C17 H1c17 . . . 120.1 ?
C15 C17 H1c17 . . . 120.1 ?
C16 C18 C19 . . . 120.7(2) ?
C16 C18 H1c18 . . . 119.63 ?
C19 C18 H1c18 . . . 119.63 ?
C18 C19 C20 . . . 120.3(2) ?
C18 C19 H1c19 . . . 119.83 ?
C20 C19 H1c19 . . . 119.83 ?
C6 C20 C19 . . . 119.3(2) ?
C6 C20 H1c20 . . . 120.35 ?
C19 C20 H1c20 . . . 120.35 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1n1 O1 . . 1_554 0.870(13) 2.161(10) 3.011(2) 165.5(19) ?
N3 H1n3 O1 . . 5_555 0.870(7) 2.013(9) 2.876(2) 171(2) ?


#=======================================================================

_database_code_depnum_ccdc_archive 'CCDC 961002'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H26 Cl2 N3 O2 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C14 H26 Cl2 N3 O2 P1'
_chemical_formula_weight         370.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration ad

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 43'
_symmetry_space_group_name_Hall  'P cw'
_symmetry_Int_Tables_number      78
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -y,x,z+3/4
4 y,-x,z+1/4
_cell_length_a                   11.3283(3)
_cell_length_b                   11.3283(3)
_cell_length_c                   14.4747(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857.54(8)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
1 1.01(5) 1 0 0 0 1 0 0 0 1
2 -0.01(5) -1 0 0 0 -1 0 0 0 -1
_cell_formula_units_Z            4

_cell_measurement_reflns_used    7467
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.74
_cell_measurement_temperature    119.8(6)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.3235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

_exptl_absorpt_coefficient_mu    0.445
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.068
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      119.8
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            27163
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         27.8
_diffrn_reflns_theta_full        27.6
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             4091
_reflns_number_gt                3393
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_gt          0.0300
_refine_ls_R_factor_all          0.0490
_refine_ls_wR_factor_ref         0.0316
_refine_ls_goodness_of_fit_ref   1.40
_refine_ls_goodness_of_fit_gt    1.46
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4091
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_number_constraints    99
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0107
_refine_ls_shift/su_mean         0.0007
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;  1876 of Friedel pairs used in the refinement
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 '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'
Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.1023 0.0942 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.49259(4) 0.72352(4) 1.00136(3) Uani 0.01708(14) 4 1 d . . .
Cl1 Cl 0.11056(5) 0.54409(7) 1.05128(4) Uani 0.0524(2) 4 1 d . . .
Cl2 Cl 0.25371(8) 0.34297(6) 1.10815(4) Uani 0.0687(3) 4 1 d . . .
O1 O 0.57127(12) 0.71793(11) 1.08269(8) Uani 0.0208(4) 4 1 d . . .
O2 O 0.36133(13) 0.58038(14) 1.15029(9) Uani 0.0334(5) 4 1 d . . .
N1 N 0.39911(14) 0.60819(14) 0.99644(10) Uani 0.0185(5) 4 1 d . . .
N2 N 0.41217(14) 0.84215(14) 1.00187(11) Uani 0.0233(5) 4 1 d . . .
N3 N 0.55349(14) 0.71190(14) 0.89856(10) Uani 0.0204(5) 4 1 d . . .
C1 C 0.34310(18) 0.55840(18) 1.06993(13) Uani 0.0216(6) 4 1 d . . .
C2 C 0.20284(18) 0.89406(18) 0.99838(15) Uani 0.0283(6) 4 1 d . . .
C3 C 0.24844(19) 0.47095(18) 1.03971(13) Uani 0.0244(6) 4 1 d . . .
C4 C 0.22670(18) 1.00261(18) 1.05711(13) Uani 0.0272(7) 4 1 d . . .
C5 C 0.62745(19) 0.60724(18) 0.87962(13) Uani 0.0270(7) 4 1 d . . .
C6 C 0.44140(18) 0.94663(18) 1.05733(14) Uani 0.0255(6) 4 1 d . . .
C7 C 0.33633(19) 0.98372(18) 1.11524(14) Uani 0.0288(7) 4 1 d . . .
C8 C 0.72518(18) 0.84478(18) 0.87832(14) Uani 0.0284(7) 4 1 d . . .
C9 C 0.80621(18) 0.73911(18) 0.85971(15) Uani 0.0278(7) 4 1 d . . .
C10 C 0.9310(2) 0.7640(2) 0.89130(18) Uani 0.0431(9) 4 1 d . . .
C11 C 0.1207(2) 1.0336(2) 1.11734(16) Uani 0.0426(8) 4 1 d . . .
C12 C 0.59844(18) 0.81705(19) 0.85198(13) Uani 0.0275(7) 4 1 d . . .
C13 C 0.30955(18) 0.85822(17) 0.94120(14) Uani 0.0245(6) 4 1 d . . .
C14 C 0.75567(19) 0.62833(19) 0.90504(14) Uani 0.0292(7) 4 1 d . . .
H1c2 H 0.137179 0.909136 0.958145 Uiso 0.034 4 1 d . . .
H2c2 H 0.17992 0.829615 1.037538 Uiso 0.034 4 1 d . . .
H1c3 H 0.255(2) 0.4448(18) 0.9768(5) Uiso 0.0293 4 1 d . . .
H1c4 H 0.240006 1.068359 1.016581 Uiso 0.0326 4 1 d . . .
H1c5 H 0.62205 0.587226 0.815316 Uiso 0.0325 4 1 d . . .
H2c5 H 0.597777 0.540969 0.913815 Uiso 0.0325 4 1 d . . .
H1c6 H 0.463659 1.010267 1.017139 Uiso 0.0306 4 1 d . . .
H2c6 H 0.506878 0.9289 1.09708 Uiso 0.0306 4 1 d . . .
H1c7 H 0.354905 1.055155 1.147822 Uiso 0.0346 4 1 d . . .
H2c7 H 0.32084 0.924588 1.161178 Uiso 0.0346 4 1 d . . .
H1c8 H 0.728765 0.865189 0.94263 Uiso 0.0341 4 1 d . . .
H2c8 H 0.752221 0.911675 0.843543 Uiso 0.0341 4 1 d . . .
H1c9 H 0.809802 0.725668 0.794285 Uiso 0.0333 4 1 d . . .
H1c10 H 0.960919 0.831833 0.859202 Uiso 0.0517 4 1 d . . .
H2c10 H 0.931201 0.779015 0.956568 Uiso 0.0517 4 1 d . . .
H3c10 H 0.979979 0.696927 0.878176 Uiso 0.0517 4 1 d . . .
H1c11 H 0.051891 1.042031 1.079181 Uiso 0.0511 4 1 d . . .
H2c11 H 0.10784 0.971866 1.161625 Uiso 0.0511 4 1 d . . .
H3c11 H 0.135619 1.106489 1.149117 Uiso 0.0511 4 1 d . . .
H1c12 H 0.549092 0.883361 0.866611 Uiso 0.033 4 1 d . . .
H2c12 H 0.593171 0.80643 0.786307 Uiso 0.033 4 1 d . . .
H1c13 H 0.293025 0.785586 0.909584 Uiso 0.0294 4 1 d . . .
H2c13 H 0.326375 0.91866 0.896618 Uiso 0.0294 4 1 d . . .
H1c14 H 0.801964 0.56103 0.887381 Uiso 0.035 4 1 d . . .
H2c14 H 0.7628 0.634723 0.97094 Uiso 0.035 4 1 d . . .
H1n1 H 0.3730(17) 0.5886(16) 0.9420(6) Uiso 0.0222 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . . 1.4780(13) ?
P1 N1 . . 1.6833(16) ?
P1 N2 . . 1.6236(16) ?
P1 N3 . . 1.6453(15) ?
Cl1 N1 . . 3.4413(17) ?
Cl1 C3 . . 1.776(2) ?
Cl2 C3 . . 1.757(2) ?
O2 C1 . . 1.207(2) ?
N1 C1 . . 1.361(2) ?
N1 H1n1 . . 0.870(11) ?
N2 C6 . . 1.468(3) ?
N2 C13 . . 1.468(3) ?
N3 C5 . . 1.477(3) ?
N3 C12 . . 1.460(3) ?
C1 C3 . . 1.524(3) ?
C2 C4 . . 1.519(3) ?
C2 C13 . . 1.520(3) ?
C2 H1c2 . . 0.96 ?
C2 H2c2 . . 0.96 ?
C3 H1c3 . . 0.960(9) ?
C4 C7 . . 1.515(3) ?
C4 C11 . . 1.525(3) ?
C4 H1c4 . . 0.96 ?
C5 C14 . . 1.517(3) ?
C5 H1c5 . . 0.96 ?
C5 H2c5 . . 0.96 ?
C6 C7 . . 1.515(3) ?
C6 H1c6 . . 0.96 ?
C6 H2c6 . . 0.96 ?
C7 H1c7 . . 0.96 ?
C7 H2c7 . . 0.96 ?
C8 C9 . . 1.532(3) ?
C8 C12 . . 1.518(3) ?
C8 H1c8 . . 0.96 ?
C8 H2c8 . . 0.96 ?
C9 C10 . . 1.512(3) ?
C9 C14 . . 1.528(3) ?
C9 H1c9 . . 0.96 ?
C10 H1c10 . . 0.96 ?
C10 H2c10 . . 0.96 ?
C10 H3c10 . . 0.96 ?
C11 H1c11 . . 0.96 ?
C11 H2c11 . . 0.96 ?
C11 H3c11 . . 0.96 ?
C12 H1c12 . . 0.96 ?
C12 H2c12 . . 0.96 ?
C13 H1c13 . . 0.96 ?
C13 H2c13 . . 0.96 ?
C14 H1c14 . . 0.96 ?
C14 H2c14 . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N1 . . . 112.32(8) ?
O1 P1 N2 . . . 111.73(8) ?
O1 P1 N3 . . . 117.65(8) ?
N1 P1 N2 . . . 106.84(8) ?
N1 P1 N3 . . . 99.41(8) ?
N2 P1 N3 . . . 107.80(8) ?
N1 Cl1 C3 . . . 40.65(7) ?
P1 N1 Cl1 . . . 138.73(8) ?
P1 N1 C1 . . . 125.58(13) ?
P1 N1 H1n1 . . . 116.7(12) ?
Cl1 N1 C1 . . . 44.72(10) ?
Cl1 N1 H1n1 . . . 80.3(12) ?
C1 N1 H1n1 . . . 116.3(12) ?
P1 N2 C6 . . . 122.91(13) ?
P1 N2 C13 . . . 122.97(13) ?
C6 N2 C13 . . . 113.93(15) ?
P1 N3 C5 . . . 118.02(12) ?
P1 N3 C12 . . . 119.90(13) ?
C5 N3 C12 . . . 111.79(15) ?
O2 C1 N1 . . . 126.00(18) ?
O2 C1 C3 . . . 122.07(18) ?
N1 C1 C3 . . . 111.91(15) ?
C4 C2 C13 . . . 112.29(17) ?
C4 C2 H1c2 . . . 109.47 ?
C4 C2 H2c2 . . . 109.47 ?
C13 C2 H1c2 . . . 109.47 ?
C13 C2 H2c2 . . . 109.47 ?
H1c2 C2 H2c2 . . . 106.5 ?
Cl1 C3 Cl2 . . . 111.21(11) ?
Cl1 C3 C1 . . . 106.77(14) ?
Cl1 C3 H1c3 . . . 107.6(13) ?
Cl2 C3 C1 . . . 110.53(14) ?
Cl2 C3 H1c3 . . . 106.1(11) ?
C1 C3 H1c3 . . . 114.7(13) ?
C2 C4 C7 . . . 110.01(17) ?
C2 C4 C11 . . . 111.48(18) ?
C2 C4 H1c4 . . . 108.3 ?
C7 C4 C11 . . . 111.13(17) ?
C7 C4 H1c4 . . . 108.67 ?
C11 C4 H1c4 . . . 107.12 ?
N3 C5 C14 . . . 111.81(16) ?
N3 C5 H1c5 . . . 109.47 ?
N3 C5 H2c5 . . . 109.47 ?
C14 C5 H1c5 . . . 109.47 ?
C14 C5 H2c5 . . . 109.47 ?
H1c5 C5 H2c5 . . . 107.03 ?
N2 C6 C7 . . . 110.42(16) ?
N2 C6 H1c6 . . . 109.47 ?
N2 C6 H2c6 . . . 109.47 ?
C7 C6 H1c6 . . . 109.47 ?
C7 C6 H2c6 . . . 109.47 ?
H1c6 C6 H2c6 . . . 108.51 ?
C4 C7 C6 . . . 112.07(17) ?
C4 C7 H1c7 . . . 109.47 ?
C4 C7 H2c7 . . . 109.47 ?
C6 C7 H1c7 . . . 109.47 ?
C6 C7 H2c7 . . . 109.47 ?
H1c7 C7 H2c7 . . . 106.74 ?
C9 C8 C12 . . . 111.14(17) ?
C9 C8 H1c8 . . . 109.47 ?
C9 C8 H2c8 . . . 109.47 ?
C12 C8 H1c8 . . . 109.47 ?
C12 C8 H2c8 . . . 109.47 ?
H1c8 C8 H2c8 . . . 107.75 ?
C8 C9 C10 . . . 111.17(17) ?
C8 C9 C14 . . . 109.98(17) ?
C8 C9 H1c9 . . . 108.83 ?
C10 C9 C14 . . . 111.94(18) ?
C10 C9 H1c9 . . . 106.75 ?
C14 C9 H1c9 . . . 108.02 ?
C9 C10 H1c10 . . . 109.47 ?
C9 C10 H2c10 . . . 109.47 ?
C9 C10 H3c10 . . . 109.47 ?
H1c10 C10 H2c10 . . . 109.47 ?
H1c10 C10 H3c10 . . . 109.47 ?
H2c10 C10 H3c10 . . . 109.47 ?
C4 C11 H1c11 . . . 109.47 ?
C4 C11 H2c11 . . . 109.47 ?
C4 C11 H3c11 . . . 109.47 ?
H1c11 C11 H2c11 . . . 109.47 ?
H1c11 C11 H3c11 . . . 109.47 ?
H2c11 C11 H3c11 . . . 109.47 ?
N3 C12 C8 . . . 112.48(16) ?
N3 C12 H1c12 . . . 109.47 ?
N3 C12 H2c12 . . . 109.47 ?
C8 C12 H1c12 . . . 109.47 ?
C8 C12 H2c12 . . . 109.47 ?
H1c12 C12 H2c12 . . . 106.28 ?
N2 C13 C2 . . . 109.70(16) ?
N2 C13 H1c13 . . . 109.47 ?
N2 C13 H2c13 . . . 109.47 ?
C2 C13 H1c13 . . . 109.47 ?
C2 C13 H2c13 . . . 109.47 ?
H1c13 C13 H2c13 . . . 109.24 ?
C5 C14 C9 . . . 112.58(17) ?
C5 C14 H1c14 . . . 109.47 ?
C5 C14 H2c14 . . . 109.47 ?
C9 C14 H1c14 . . . 109.47 ?
C9 C14 H2c14 . . . 109.47 ?
H1c14 C14 H2c14 . . . 106.17 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H1c3 O2 . . 3_654 0.960(9) 2.37(2) 3.062(2) 128.9(16) ?
N1 H1n1 O1 . . 3_654 0.870(11) 1.899(13) 2.7479(19) 164.9(18) ?


#=======================================================================


_database_code_depnum_ccdc_archive 'CCDC 961004'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H28 Cl2 N3 O2 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C19 H28 Cl2 N3 O2 P1'
_chemical_formula_weight         432.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
_cell_length_a                   13.2836(3)
_cell_length_b                   9.9293(2)
_cell_length_c                   17.5975(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.596(2)
_cell_angle_gamma                90
_cell_volume                     2186.62(9)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    16170
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.8
_cell_measurement_temperature    119.9(6)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.3128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             912

_exptl_absorpt_coefficient_mu    0.389
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.126
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  1

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      119.9
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            39585
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_full        27.05
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; 
Two rings in the structure were found to be slightly disordered.
The disorder of each ring was modeled by a rigid body placed to 
two actual positions in the crystal. The positions were distinguished by 
rotation angles. For each position we refined an occupancy, keeping 
the sum of occupancies for each pair of positions equal to the full 
occupancy. 
The shape of the rigid body was refined as well as anisotropic ADPs of 
all non-H atoms.

All hydrogen atoms were discernible in difference Fourier maps and could be
refined to reasonable geometry, but according to common practice H atoms 
bonded to C were kept in ideal positions with C--H = 0.96 Å. Uiso(H) 
was set to 1.2Ueq(C,N). All non-hydrogen atoms were refined using 
harmonic refinement. 

Position of the hydrogen H1N3 was refined while for its ADP the above 
mentioned constraint was applied.   
;

_reflns_number_total             4881
_reflns_number_gt                3868
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_gt          0.0332
_refine_ls_R_factor_all          0.0453
_refine_ls_wR_factor_ref         0.0348
_refine_ls_goodness_of_fit_ref   1.74
_refine_ls_goodness_of_fit_gt    1.88
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4881
_refine_ls_number_parameters     261
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(F)+0.0001F²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0203
_refine_ls_shift/su_mean         0.0008
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 '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'
Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
P 0.1023 0.0942 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.67275(3) 0.57274(3) 0.06352(2) Uani 0.01655(11) 4 1 d . . .
Cl1 Cl 0.54913(3) 0.28921(4) 0.21902(2) Uani 0.03112(14) 4 1 d . . .
Cl2 Cl 0.73392(3) 0.08526(4) 0.01198(3) Uani 0.03647(15) 4 1 d . . .
O1 O 0.57135(7) 0.64207(8) 0.01990(6) Uani 0.0214(3) 4 1 d . . .
O2 O 0.79320(7) 0.31623(9) 0.15631(6) Uani 0.0242(3) 4 1 d . . .
N3 N 0.63737(8) 0.41205(10) 0.07504(7) Uani 0.0175(4) 4 1 d . . .
C1 C 0.53999(12) -0.06985(14) 0.11785(9) Uani 0.0308(5) 4 1 d . . .
C2 C 0.52195(12) 0.03653(13) 0.16205(9) Uani 0.0294(5) 4 1 d . . .
C4 C 0.65397(11) 0.06844(13) 0.07200(9) Uani 0.0238(5) 4 1 d . . .
C5 C 0.57113(11) 0.15852(12) 0.16042(8) Uani 0.0227(5) 4 1 d . . .
C9 C 0.69868(10) 0.30930(12) 0.11828(8) Uani 0.0180(5) 4 1 d . . .
C11 C 0.63859(10) 0.17868(12) 0.11579(8) Uani 0.0188(4) 4 1 d . . .
C12 C 0.60557(12) -0.05454(13) 0.07251(9) Uani 0.0289(5) 4 1 d . . .
H1c1 H 0.506464 -0.155185 0.118815 Uiso 0.037 4 1 d . . .
H1c2 H 0.475803 0.025906 0.193528 Uiso 0.0352 4 1 d . . .
H1c12 H 0.617658 -0.128487 0.041491 Uiso 0.0347 4 1 d . . .
H1n3 H 0.5710(3) 0.3947(13) 0.0472(7) Uiso 0.021 4 1 d . . .
N1a N 0.7378(7) 0.6208(12) 0.1537(5) Uani 0.0186(6) 4 0.586(15) d . . .
C6a C 0.9168(6) 0.6567(11) 0.2504(5) Uani 0.0303(14) 4 0.586(15) d . . .
C7a C 0.7724(6) 0.5587(8) 0.2949(4) Uani 0.0243(12) 4 0.586(15) d . . .
C8a C 0.8747(5) 0.6424(8) 0.3209(4) Uani 0.0293(10) 4 0.586(15) d . . .
C13a C 0.8317(8) 0.7102(12) 0.1759(6) Uani 0.0260(11) 4 0.586(15) d . . .
C14a C 0.9580(7) 0.5839(11) 0.3953(4) Uani 0.0518(17) 4 0.586(15) d . . .
C19a C 0.6910(5) 0.6117(11) 0.2182(5) Uani 0.0221(10) 4 0.586(15) d . . .
H1c6a H 0.97709 0.716457 0.265325 Uiso 0.0363 4 0.586(15) d . . .
H2c6a H 0.941104 0.570705 0.238594 Uiso 0.0363 4 0.586(15) d . . .
H1c7a H 0.789294 0.466841 0.287013 Uiso 0.0292 4 0.586(15) d . . .
H2c7a H 0.74207 0.558277 0.337289 Uiso 0.0292 4 0.586(15) d . . .
H1c8a H 0.858602 0.730732 0.335754 Uiso 0.0352 4 0.586(15) d . . .
H1c13a H 0.811042 0.79898 0.186462 Uiso 0.0312 4 0.586(15) d . . .
H2c13a H 0.859544 0.71434 0.132131 Uiso 0.0312 4 0.586(15) d . . .
H1c14a H 1.023271 0.634082 0.407237 Uiso 0.0622 4 0.586(15) d . . .
H2c14a H 0.932548 0.589151 0.440224 Uiso 0.0622 4 0.586(15) d . . .
H3c14a H 0.970925 0.491431 0.385511 Uiso 0.0622 4 0.586(15) d . . .
H1c19a H 0.630345 0.55249 0.20166 Uiso 0.0265 4 0.586(15) d . . .
H2c19a H 0.667327 0.699294 0.228045 Uiso 0.0265 4 0.586(15) d . . .
N1b N 0.7441(17) 0.626(3) 0.1550(12) Uani 0.0186(6) 4 0.414(15) d . . .
C6b C 0.9236(17) 0.684(3) 0.2436(13) Uani 0.0303(14) 4 0.414(15) d . . .
C7b C 0.7997(17) 0.555(3) 0.2963(12) Uani 0.0243(12) 4 0.414(15) d . . .
C8b C 0.8928(17) 0.654(3) 0.3181(12) Uani 0.0293(9) 4 0.414(15) d . . .
C13b C 0.8282(18) 0.730(3) 0.1735(13) Uani 0.0260(11) 4 0.414(15) d . . .
C14b C 0.9870(17) 0.603(3) 0.3882(12) Uani 0.0518(17) 4 0.414(15) d . . .
C19b C 0.7075(17) 0.601(3) 0.2237(13) Uani 0.0221(10) 4 0.414(15) d . . .
H1c6b H 0.977521 0.753056 0.256347 Uiso 0.0363 4 0.414(15) d . . .
H2c6b H 0.95389 0.605096 0.228535 Uiso 0.0363 4 0.414(15) d . . .
H1c7b H 0.823776 0.467964 0.285506 Uiso 0.0292 4 0.414(15) d . . .
H2c7b H 0.775491 0.543694 0.341527 Uiso 0.0292 4 0.414(15) d . . .
H1c8b H 0.870588 0.736598 0.335958 Uiso 0.0352 4 0.414(15) d . . .
H1c13b H 0.801062 0.812502 0.187261 Uiso 0.0312 4 0.414(15) d . . .
H2c13b H 0.84945 0.744211 0.127134 Uiso 0.0312 4 0.414(15) d . . .
H1c14b H 1.046225 0.663766 0.397316 Uiso 0.0622 4 0.414(15) d . . .
H2c14b H 0.96729 0.598308 0.435821 Uiso 0.0622 4 0.414(15) d . . .
H3c14b H 1.007173 0.5152 0.375685 Uiso 0.0622 4 0.414(15) d . . .
H1c19b H 0.653078 0.532601 0.209399 Uiso 0.0265 4 0.414(15) d . . .
H2c19b H 0.677524 0.68183 0.236815 Uiso 0.0265 4 0.414(15) d . . .
N2a N 0.7575(15) 0.5841(17) 0.0132(9) Uani 0.0211(4) 4 0.29(2) d . . .
C3a C 0.8701(13) 0.4073(17) -0.0132(7) Uani 0.0276(9) 4 0.29(2) d . . .
C10a C 0.8362(9) 0.4467(11) -0.1018(7) Uani 0.0256(8) 4 0.29(2) d . . .
C15a C 0.7218(13) 0.6270(12) -0.0716(11) Uani 0.0245(7) 4 0.29(2) d . . .
C16a C 0.8402(11) 0.3277(13) -0.1549(9) Uani 0.0389(15) 4 0.29(2) d . . .
C17a C 0.7257(10) 0.5108(14) -0.1269(8) Uani 0.0251(10) 4 0.29(2) d . . .
C18a C 0.8646(15) 0.524(2) 0.0407(8) Uani 0.0249(9) 4 0.29(2) d . . .
H1c3a H 0.825474 0.335353 -0.006551 Uiso 0.0331 4 0.29(2) d . . .
H2c3a H 0.941586 0.372285 0.00378 Uiso 0.0331 4 0.29(2) d . . .
H1c10a H 0.885867 0.511617 -0.10898 Uiso 0.0307 4 0.29(2) d . . .
H1c15a H 0.766625 0.698882 -0.078019 Uiso 0.0294 4 0.29(2) d . . .
H2c15a H 0.650074 0.660829 -0.086617 Uiso 0.0294 4 0.29(2) d . . .
H1c16a H 0.821474 0.356957 -0.209875 Uiso 0.0467 4 0.29(2) d . . .
H2c16a H 0.91104 0.290687 -0.137389 Uiso 0.0467 4 0.29(2) d . . .
H3c16a H 0.79049 0.260082 -0.150915 Uiso 0.0467 4 0.29(2) d . . .
H1c17a H 0.673969 0.443973 -0.125802 Uiso 0.0302 4 0.29(2) d . . .
H2c17a H 0.706619 0.542709 -0.181353 Uiso 0.0302 4 0.29(2) d . . .
H1c18a H 0.881247 0.493189 0.095135 Uiso 0.0299 4 0.29(2) d . . .
H2c18a H 0.916173 0.591342 0.039497 Uiso 0.0299 4 0.29(2) d . . .
N2b N 0.754(3) 0.580(3) 0.0133(15) Uani 0.0211(4) 4 0.71(2) d . . .
C3b C 0.860(2) 0.408(3) -0.0256(14) Uani 0.0276(9) 4 0.71(2) d . . .
C10b C 0.834(2) 0.470(3) -0.1091(14) Uani 0.0256(8) 4 0.71(2) d . . .
C15b C 0.726(3) 0.644(3) -0.0662(16) Uani 0.0245(7) 4 0.71(2) d . . .
C16b C 0.835(2) 0.366(3) -0.1719(15) Uani 0.0389(15) 4 0.71(2) d . . .
C17b C 0.727(2) 0.543(3) -0.1308(15) Uani 0.0251(10) 4 0.71(2) d . . .
C18b C 0.858(3) 0.510(3) 0.0377(15) Uani 0.0249(9) 4 0.71(2) d . . .
H1c3b H 0.810752 0.336675 -0.027425 Uiso 0.0331 4 0.71(2) d . . .
H2c3b H 0.929758 0.366744 -0.010172 Uiso 0.0331 4 0.71(2) d . . .
H1c10b H 0.888463 0.534265 -0.108298 Uiso 0.0307 4 0.71(2) d . . .
H1c15b H 0.776079 0.715288 -0.064125 Uiso 0.0294 4 0.71(2) d . . .
H2c15b H 0.656452 0.683694 -0.079814 Uiso 0.0294 4 0.71(2) d . . .
H1c16b H 0.821219 0.408911 -0.223193 Uiso 0.0467 4 0.71(2) d . . .
H2c16b H 0.903511 0.322458 -0.156186 Uiso 0.0467 4 0.71(2) d . . .
H3c16b H 0.780571 0.299578 -0.176084 Uiso 0.0467 4 0.71(2) d . . .
H1c17b H 0.671138 0.478641 -0.137832 Uiso 0.0302 4 0.71(2) d . . .
H2c17b H 0.713354 0.588906 -0.181397 Uiso 0.0302 4 0.71(2) d . . .
H1c18b H 0.869389 0.465249 0.088269 Uiso 0.0299 4 0.71(2) d . . .
H2c18b H 0.913884 0.574885 0.044636 Uiso 0.0299 4 0.71(2) d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 . . 1.4778(8) ?
P1 N3 . . 1.6946(11) ?
P1 N1a . . 1.604(8) ?
P1 N2a . . 1.65(2) ?
Cl1 N3 . . 3.3575(13) ?
Cl1 C5 . . 1.7421(15) ?
Cl2 C4 . . 1.7389(17) ?
O2 C9 . . 1.2106(14) ?
N3 C9 . . 1.3665(15) ?
N3 H1n3 . . 0.870(5) ?
C1 C2 . . 1.380(2) ?
C1 C12 . . 1.373(3) ?
C1 H1c1 . . 0.96 ?
C2 C5 . . 1.3810(19) ?
C2 H1c2 . . 0.96 ?
C4 C11 . . 1.3926(19) ?
C4 C12 . . 1.3815(19) ?
C5 C11 . . 1.390(2) ?
C9 C11 . . 1.5158(17) ?
C12 H1c12 . . 0.96 ?
N1a C13a . . 1.473(15) ?
N1a C19a . . 1.469(14) ?
C6a C8a . . 1.529(13) ?
C6a C13a . . 1.511(11) ?
C6a H1c6a . . 0.96 ?
C6a H2c6a . . 0.96 ?
C7a C8a . . 1.526(10) ?
C7a C19a . . 1.514(10) ?
C7a H1c7a . . 0.96 ?
C7a H2c7a . . 0.96 ?
C8a C14a . . 1.518(10) ?
C8a H1c8a . . 0.96 ?
C13a H1c13a . . 0.96 ?
C13a H2c13a . . 0.96 ?
C14a H1c14a . . 0.96 ?
C14a H2c14a . . 0.96 ?
C14a H3c14a . . 0.96 ?
C19a H1c19a . . 0.96 ?
C19a H2c19a . . 0.96 ?
N2a C15a . . 1.47(2) ?
N2a C18a . . 1.47(3) ?
C3a C10a . . 1.523(17) ?
C3a C18a . . 1.52(3) ?
C3a H1c3a . . 0.96 ?
C3a H2c3a . . 0.96 ?
C10a C16a . . 1.518(19) ?
C10a C17a . . 1.522(17) ?
C10a H1c10a . . 0.96 ?
C15a C17a . . 1.52(2) ?
C15a H1c15a . . 0.96 ?
C15a H2c15a . . 0.96 ?
C16a H1c16a . . 0.96 ?
C16a H2c16a . . 0.96 ?
C16a H3c16a . . 0.96 ?
C17a H1c17a . . 0.96 ?
C17a H2c17a . . 0.96 ?
C18a H1c18a . . 0.96 ?
C18a H2c18a . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 P1 N3 . . . 105.05(5) ?
O1 P1 N1a . . . 118.1(4) ?
O1 P1 N2a . . . 110.8(5) ?
N3 P1 N1a . . . 103.9(4) ?
N3 P1 N2a . . . 113.2(6) ?
N1a P1 N2a . . . 105.8(6) ?
N3 Cl1 C5 . . . 69.73(5) ?
P1 N3 Cl1 . . . 127.83(6) ?
P1 N3 C9 . . . 129.21(8) ?
P1 N3 H1n3 . . . 112.8(8) ?
Cl1 N3 C9 . . . 66.57(8) ?
Cl1 N3 H1n3 . . . 79.0(8) ?
C9 N3 H1n3 . . . 117.9(8) ?
C2 C1 C12 . . . 120.46(14) ?
C2 C1 H1c1 . . . 119.77 ?
C12 C1 H1c1 . . . 119.77 ?
C1 C2 C5 . . . 119.15(16) ?
C1 C2 H1c2 . . . 120.43 ?
C5 C2 H1c2 . . . 120.43 ?
Cl2 C4 C11 . . . 119.57(11) ?
Cl2 C4 C12 . . . 117.98(12) ?
C11 C4 C12 . . . 122.43(15) ?
Cl1 C5 C2 . . . 117.82(13) ?
Cl1 C5 C11 . . . 119.67(10) ?
C2 C5 C11 . . . 122.49(13) ?
O2 C9 N3 . . . 125.40(11) ?
O2 C9 C11 . . . 120.20(10) ?
N3 C9 C11 . . . 114.39(10) ?
C4 C11 C5 . . . 116.20(12) ?
C4 C11 C9 . . . 120.99(14) ?
C5 C11 C9 . . . 122.68(12) ?
C1 C12 C4 . . . 119.28(14) ?
C1 C12 H1c12 . . . 120.36 ?
C4 C12 H1c12 . . . 120.36 ?
P1 N1a C13a . . . 124.6(8) ?
P1 N1a C19a . . . 121.3(7) ?
C13a N1a C19a . . . 111.9(8) ?
C8a C6a C13a . . . 111.5(7) ?
C8a C6a H1c6a . . . 109.47 ?
C8a C6a H2c6a . . . 109.47 ?
C13a C6a H1c6a . . . 109.47 ?
C13a C6a H2c6a . . . 109.47 ?
H1c6a C6a H2c6a . . . 107.37 ?
C8a C7a C19a . . . 112.1(7) ?
C8a C7a H1c7a . . . 109.47 ?
C8a C7a H2c7a . . . 109.47 ?
C19a C7a H1c7a . . . 109.47 ?
C19a C7a H2c7a . . . 109.47 ?
H1c7a C7a H2c7a . . . 106.7 ?
C6a C8a C7a . . . 109.8(6) ?
C6a C8a C14a . . . 112.1(6) ?
C6a C8a H1c8a . . . 108.18 ?
C7a C8a C14a . . . 111.6(7) ?
C7a C8a H1c8a . . . 108.76 ?
C14a C8a H1c8a . . . 106.21 ?
N1a C13a C6a . . . 109.8(9) ?
N1a C13a H1c13a . . . 109.47 ?
N1a C13a H2c13a . . . 109.47 ?
C6a C13a H1c13a . . . 109.47 ?
C6a C13a H2c13a . . . 109.47 ?
H1c13a C13a H2c13a . . . 109.18 ?
C8a C14a H1c14a . . . 109.47 ?
C8a C14a H2c14a . . . 109.47 ?
C8a C14a H3c14a . . . 109.47 ?
H1c14a C14a H2c14a . . . 109.47 ?
H1c14a C14a H3c14a . . . 109.47 ?
H2c14a C14a H3c14a . . . 109.47 ?
N1a C19a C7a . . . 110.4(7) ?
N1a C19a H1c19a . . . 109.47 ?
N1a C19a H2c19a . . . 109.47 ?
C7a C19a H1c19a . . . 109.47 ?
C7a C19a H2c19a . . . 109.47 ?
H1c19a C19a H2c19a . . . 108.52 ?
P1 N2a C15a . . . 121.2(14) ?
P1 N2a C18a . . . 123.7(13) ?
C15a N2a C18a . . . 113.6(17) ?
C10a C3a C18a . . . 112.5(13) ?
C10a C3a H1c3a . . . 109.47 ?
C10a C3a H2c3a . . . 109.47 ?
C18a C3a H1c3a . . . 109.47 ?
C18a C3a H2c3a . . . 109.47 ?
H1c3a C3a H2c3a . . . 106.23 ?
C3a C10a C16a . . . 111.7(11) ?
C3a C10a C17a . . . 109.2(12) ?
C3a C10a H1c10a . . . 109.06 ?
C16a C10a C17a . . . 112.1(9) ?
C16a C10a H1c10a . . . 105.96 ?
C17a C10a H1c10a . . . 108.67 ?
N2a C15a C17a . . . 111.1(12) ?
N2a C15a H1c15a . . . 109.47 ?
N2a C15a H2c15a . . . 109.47 ?
C17a C15a H1c15a . . . 109.47 ?
C17a C15a H2c15a . . . 109.47 ?
H1c15a C15a H2c15a . . . 107.76 ?
C10a C16a H1c16a . . . 109.47 ?
C10a C16a H2c16a . . . 109.47 ?
C10a C16a H3c16a . . . 109.47 ?
H1c16a C16a H2c16a . . . 109.47 ?
H1c16a C16a H3c16a . . . 109.47 ?
H2c16a C16a H3c16a . . . 109.47 ?
C10a C17a C15a . . . 111.6(10) ?
C10a C17a H1c17a . . . 109.47 ?
C10a C17a H2c17a . . . 109.47 ?
C15a C17a H1c17a . . . 109.47 ?
C15a C17a H2c17a . . . 109.47 ?
H1c17a C17a H2c17a . . . 107.23 ?
N2a C18a C3a . . . 110.4(13) ?
N2a C18a H1c18a . . . 109.47 ?
N2a C18a H2c18a . . . 109.47 ?
C3a C18a H1c18a . . . 109.47 ?
C3a C18a H2c18a . . . 109.47 ?
H1c18a C18a H2c18a . . . 108.51 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H1c12 O1 . . 1_545 0.96 2.36 3.1395(15) 138.29 ?
N3 H1n3 O1 . . 3_665 0.870(5) 1.899(6) 2.7676(12) 176.2(12) ?
C13a H2c13a N2a . . . 0.96 2.45 2.974(19) 114.28 ?
C13a H2c13a C18a . . . 0.96 2.50 3.15(2) 125.85 ?
C15a H2c15a O1 . . . 0.96 2.44 2.96(2) 113.79 ?


#=======================================================================

_database_code_depnum_ccdc_archive 'CCDC 961005'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C35 H32 Cl2 N3 O2 P1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C35 H32 Cl2 N3 O2 P1'
_chemical_formula_weight         628.5
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   11.3453(4)
_cell_length_b                   12.3967(4)
_cell_length_c                   25.1236(8)
_cell_angle_alpha                94.263(2)
_cell_angle_beta                 98.121(3)
_cell_angle_gamma                116.378(3)
_cell_volume                     3096.2(2)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
? ? ? ? ? ? ? ? ? ? ?
_cell_formula_units_Z            4

_cell_measurement_reflns_used    11885
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      66.99
_cell_measurement_temperature    120.00(14)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1312

_exptl_absorpt_coefficient_mu    2.665
_exptl_crystal_description       ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.203
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
analytical: 
   CrysAlisPro, Agilent Technologies, Version 1.171.35.19
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_T_max  0.723

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            21428
_diffrn_reflns_theta_min         3.6
_diffrn_reflns_theta_max         67.1
_diffrn_reflns_theta_full        66.88
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             10806
_reflns_number_gt                8878
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_gt          0.0656
_refine_ls_R_factor_all          0.0387
_refine_ls_wR_factor_ref         0.0698
_refine_ls_goodness_of_fit_ref   1.37
_refine_ls_goodness_of_fit_gt    1.44
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         10806
_refine_ls_number_parameters     781
_refine_ls_number_restraints     0
_refine_ls_number_constraints    250
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0242
_refine_ls_shift/su_mean         0.0011
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

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'
Cl 0.3639 0.7018 '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'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl13a Cl 0.83584(4) 1.12138(4) 0.267269(17) Uani 0.03000(15) 2 1 d . . .
Cl12a Cl 0.33720(4) 1.08451(3) 0.218071(16) Uani 0.02577(14) 2 1 d . . .
Cl13b Cl 0.29068(4) 0.41394(4) 0.280663(19) Uani 0.03431(16) 2 1 d . . .
Cl12b Cl -0.15630(5) 0.45332(4) 0.202911(18) Uani 0.03502(17) 2 1 d . . .
P1a P 0.41302(4) 0.76416(3) 0.163974(15) Uani 0.01801(14) 2 1 d . . .
P1b P 0.26062(4) 0.77245(3) 0.326118(16) Uani 0.01794(14) 2 1 d . . .
O2b O 0.35605(10) 0.86691(9) 0.29940(4) Uani 0.0215(4) 2 1 d . . .
O2a O 0.31924(11) 0.67015(9) 0.19137(4) Uani 0.0227(4) 2 1 d . . .
O5b O 0.04018(11) 0.50713(9) 0.32168(5) Uani 0.0248(4) 2 1 d . . .
O5a O 0.60422(11) 1.03557(9) 0.15837(5) Uani 0.0267(4) 2 1 d . . .
N3b N 0.20398(13) 0.64083(11) 0.28265(6) Uani 0.0205(5) 2 1 d . . .
N29b N 0.31797(13) 0.74790(10) 0.38533(5) Uani 0.0199(5) 2 1 d . . .
N29a N 0.54817(13) 0.75495(11) 0.15300(5) Uani 0.0198(5) 2 1 d . . .
N14a N 0.33557(12) 0.76926(11) 0.10478(5) Uani 0.0202(5) 2 1 d . . .
N14b N 0.14016(13) 0.80554(11) 0.33702(5) Uani 0.0195(5) 2 1 d . . .
N3a N 0.47221(13) 0.89650(11) 0.20694(6) Uani 0.0192(5) 2 1 d . . .
C31b C 0.30957(17) 0.58780(13) 0.44236(7) Uani 0.0256(6) 2 1 d . . .
C4b C 0.10220(15) 0.52963(13) 0.28480(6) Uani 0.0199(6) 2 1 d . . .
C23a C 0.17729(15) 0.56937(14) 0.04793(7) Uani 0.0244(6) 2 1 d . . .
C11a C 0.71855(16) 1.17120(13) 0.27742(7) Uani 0.0226(6) 2 1 d . . .
C16a C 0.34481(15) 0.90942(13) 0.03763(7) Uani 0.0245(6) 2 1 d . . .
C42b C 0.74608(17) 0.96542(14) 0.49670(7) Uani 0.0269(6) 2 1 d . . .
C8a C 0.53528(18) 1.25206(13) 0.29618(7) Uani 0.0281(7) 2 1 d . . .
C7b C -0.04771(16) 0.39127(13) 0.19785(7) Uani 0.0244(6) 2 1 d . . .
C11b C 0.14800(16) 0.37394(13) 0.23153(7) Uani 0.0243(6) 2 1 d . . .
C20a C 0.25675(19) 1.05341(16) 0.04562(9) Uani 0.0372(8) 2 1 d . . .
C4a C 0.55657(15) 1.01154(13) 0.19887(6) Uani 0.0194(6) 2 1 d . . .
C38b C 0.53222(16) 0.91976(13) 0.44059(7) Uani 0.0217(6) 2 1 d . . .
C30a C 0.53591(16) 0.66883(13) 0.10637(7) Uani 0.0228(6) 2 1 d . . .
C34a C 0.50086(18) 0.31754(15) 0.13297(8) Uani 0.0327(7) 2 1 d . . .
C20b C -0.29910(17) 0.59627(14) 0.30885(7) Uani 0.0276(6) 2 1 d . . .
C17b C -0.13979(17) 0.79304(14) 0.38911(7) Uani 0.0281(6) 2 1 d . . .
C6a C 0.59022(16) 1.11162(13) 0.24543(6) Uani 0.0207(6) 2 1 d . . .
C41b C 0.81301(17) 1.04270(14) 0.46212(7) Uani 0.0293(6) 2 1 d . . .
C7a C 0.49992(16) 1.15413(13) 0.25600(7) Uani 0.0224(6) 2 1 d . . .
C37b C 0.37986(15) 0.85319(13) 0.43014(6) Uani 0.0213(6) 2 1 d . . .
C15b C 0.06586(15) 0.76766(13) 0.38167(6) Uani 0.0215(6) 2 1 d . . .
C16b C -0.08224(15) 0.72939(13) 0.36459(6) Uani 0.0212(6) 2 1 d . . .
C6b C 0.06856(15) 0.43165(13) 0.23706(7) Uani 0.0215(6) 2 1 d . . .
C35a C 0.46336(17) 0.37963(14) 0.16957(8) Uani 0.0290(6) 2 1 d . . .
C17a C 0.32617(16) 0.90829(15) -0.01825(7) Uani 0.0288(6) 2 1 d . . .
C21b C -0.16429(16) 0.62941(13) 0.32456(7) Uani 0.0244(6) 2 1 d . . .
C41a C 1.03093(17) 0.85873(15) 0.14756(8) Uani 0.0312(7) 2 1 d . . .
C40a C 0.96287(17) 0.75376(15) 0.16905(7) Uani 0.0295(7) 2 1 d . . .
C26a C 0.15055(18) 0.36662(17) -0.01892(9) Uani 0.0379(7) 2 1 d . . .
C22a C 0.19305(15) 0.67934(13) 0.08423(7) Uani 0.0233(6) 2 1 d . . .
C10b C 0.11566(17) 0.28200(14) 0.18879(8) Uani 0.0298(7) 2 1 d . . .
C39b C 0.60089(17) 0.99714(14) 0.40585(7) Uani 0.0287(7) 2 1 d . . .
C36b C 0.4020(2) 0.58674(15) 0.48455(8) Uani 0.0332(7) 2 1 d . . .
C18b C -0.27520(17) 0.76002(15) 0.37366(8) Uani 0.0339(7) 2 1 d . . .
C39a C 0.84332(17) 0.73056(15) 0.18526(7) Uani 0.0259(6) 2 1 d . . .
C36a C 0.47285(16) 0.49319(14) 0.16164(7) Uani 0.0258(6) 2 1 d . . .
C38a C 0.79065(15) 0.81221(13) 0.18103(6) Uani 0.0218(6) 2 1 d . . .
C22b C 0.11441(15) 0.89270(13) 0.30663(7) Uani 0.0219(6) 2 1 d . . .
C23b C 0.16090(16) 1.01579(13) 0.34088(7) Uani 0.0227(6) 2 1 d . . .
C31a C 0.52290(15) 0.54618(13) 0.11768(7) Uani 0.0229(6) 2 1 d . . .
C25a C 0.16906(19) 0.37109(16) 0.03703(9) Uani 0.0385(8) 2 1 d . . .
C28a C 0.15876(16) 0.56393(15) -0.00838(7) Uani 0.0279(6) 2 1 d . . .
C43b C 0.60609(16) 0.90531(13) 0.48591(7) Uani 0.0245(6) 2 1 d . . .
C10a C 0.75648(17) 1.26843(14) 0.31816(7) Uani 0.0282(6) 2 1 d . . .
C19a C 0.23744(19) 1.05086(16) -0.01032(8) Uani 0.0379(8) 2 1 d . . .
C33b C 0.1319(2) 0.46058(18) 0.48632(9) Uani 0.0434(9) 2 1 d . . .
C27a C 0.14588(17) 0.46292(16) -0.04146(8) Uani 0.0338(7) 2 1 d . . .
C15a C 0.40527(16) 0.83441(14) 0.06307(6) Uani 0.0231(6) 2 1 d . . .
C43a C 0.86085(17) 0.91883(15) 0.16079(7) Uani 0.0293(7) 2 1 d . . .
C19b C -0.35527(17) 0.66121(15) 0.33316(8) Uani 0.0309(7) 2 1 d . . .
C24a C 0.18247(17) 0.47203(14) 0.07043(8) Uani 0.0309(7) 2 1 d . . .
C32b C 0.17384(19) 0.52423(15) 0.44357(8) Uani 0.0340(7) 2 1 d . . .
C24b C 0.29625(16) 1.08954(13) 0.36262(7) Uani 0.0237(6) 2 1 d . . .
C37a C 0.66041(16) 0.78511(14) 0.19936(7) Uani 0.0223(6) 2 1 d . . .
C8b C -0.08236(18) 0.30014(14) 0.15430(7) Uani 0.0288(6) 2 1 d . . .
C30b C 0.35725(16) 0.65133(13) 0.39458(7) Uani 0.0231(6) 2 1 d . . .
C9a C 0.66358(18) 1.30789(14) 0.32724(7) Uani 0.0305(7) 2 1 d . . .
C42a C 0.97971(18) 0.94098(15) 0.14364(8) Uani 0.0342(7) 2 1 d . . .
C32a C 0.55902(17) 0.48249(15) 0.08098(7) Uani 0.0286(7) 2 1 d . . .
C34b C 0.2255(2) 0.46066(17) 0.52832(8) Uani 0.0451(9) 2 1 d . . .
C18a C 0.27313(18) 0.97876(16) -0.04212(8) Uani 0.0351(7) 2 1 d . . .
C40b C 0.74047(18) 1.05828(16) 0.41687(8) Uani 0.0333(7) 2 1 d . . .
C28b C 0.07009(17) 1.05894(15) 0.34967(8) Uani 0.0299(7) 2 1 d . . .
C21a C 0.31032(17) 0.98365(14) 0.06947(7) Uani 0.0299(7) 2 1 d . . .
C35b C 0.3603(2) 0.52337(16) 0.52737(8) Uani 0.0422(9) 2 1 d . . .
C25b C 0.33957(17) 1.20324(14) 0.39274(7) Uani 0.0284(6) 2 1 d . . .
C27b C 0.11347(19) 1.17289(15) 0.37985(8) Uani 0.0353(8) 2 1 d . . .
C33a C 0.54707(19) 0.36846(15) 0.08836(8) Uani 0.0356(7) 2 1 d . . .
C9b C 0.00105(18) 0.24714(14) 0.14994(7) Uani 0.0295(7) 2 1 d . . .
C26b C 0.24838(19) 1.24531(15) 0.40187(7) Uani 0.0317(7) 2 1 d . . .
H1n3a H 0.4420(18) 0.8894(15) 0.2368(8) Uiso 0.0231 2 1 d . . .
H1n3b H 0.2365(19) 0.6484(16) 0.2555(9) Uiso 0.0246 2 1 d . . .
H1c42b H 0.795569 0.953216 0.527904 Uiso 0.0323 2 1 d . . .
H1c8a H 0.471598 1.28061 0.302316 Uiso 0.0337 2 1 d . . .
H1c20a H 0.232812 1.10387 0.06795 Uiso 0.0447 2 1 d . . .
H1c30a H 0.609722 0.70721 0.088225 Uiso 0.0274 2 1 d . . .
H2c30a H 0.462422 0.657013 0.078385 Uiso 0.0274 2 1 d . . .
H1c34a H 0.494803 0.239613 0.138559 Uiso 0.0393 2 1 d . . .
H1c20b H -0.354228 0.52774 0.280879 Uiso 0.0331 2 1 d . . .
H1c17b H -0.084895 0.861194 0.417282 Uiso 0.0337 2 1 d . . .
H1c41b H 0.909263 1.085306 0.469455 Uiso 0.0351 2 1 d . . .
H1c37b H 0.350699 0.826252 0.462982 Uiso 0.0255 2 1 d . . .
H2c37b H 0.345204 0.909579 0.422656 Uiso 0.0255 2 1 d . . .
H1c15b H 0.104232 0.833239 0.411717 Uiso 0.0257 2 1 d . . .
H2c15b H 0.077315 0.701717 0.395084 Uiso 0.0257 2 1 d . . .
H1c35a H 0.430687 0.344408 0.200544 Uiso 0.0347 2 1 d . . .
H1c17a H 0.350261 0.858135 -0.040687 Uiso 0.0345 2 1 d . . .
H1c21b H -0.126865 0.583039 0.307708 Uiso 0.0292 2 1 d . . .
H1c41a H 1.112848 0.874364 0.135492 Uiso 0.0375 2 1 d . . .
H1c40a H 0.998557 0.69692 0.172729 Uiso 0.0354 2 1 d . . .
H1c26a H 0.141013 0.296676 -0.041907 Uiso 0.0455 2 1 d . . .
H1c22a H 0.147272 0.71782 0.064673 Uiso 0.028 2 1 d . . .
H2c22a H 0.149657 0.653671 0.114434 Uiso 0.028 2 1 d . . .
H1c10b H 0.171897 0.243228 0.186227 Uiso 0.0357 2 1 d . . .
H1c39b H 0.551763 1.008313 0.374204 Uiso 0.0344 2 1 d . . .
H1c36b H 0.496034 0.630322 0.484216 Uiso 0.0398 2 1 d . . .
H1c18b H -0.313258 0.80531 0.390918 Uiso 0.0406 2 1 d . . .
H1c39a H 0.796057 0.656862 0.199655 Uiso 0.031 2 1 d . . .
H1c36a H 0.444644 0.534893 0.186701 Uiso 0.0309 2 1 d . . .
H1c22b H 0.020313 0.85833 0.291624 Uiso 0.0262 2 1 d . . .
H2c22b H 0.157388 0.903747 0.275758 Uiso 0.0262 2 1 d . . .
H1c25a H 0.17266 0.304167 0.052812 Uiso 0.0462 2 1 d . . .
H1c28a H 0.154849 0.63045 -0.024434 Uiso 0.0334 2 1 d . . .
H1c43b H 0.559949 0.852863 0.510355 Uiso 0.0294 2 1 d . . .
H1c10a H 0.84563 1.307724 0.339699 Uiso 0.0339 2 1 d . . .
H1c19a H 0.199599 1.098788 -0.026783 Uiso 0.0455 2 1 d . . .
H1c33b H 0.037932 0.416518 0.486728 Uiso 0.0521 2 1 d . . .
H1c27a H 0.133673 0.46021 -0.080218 Uiso 0.0406 2 1 d . . .
H1c15a H 0.404967 0.776892 0.035194 Uiso 0.0277 2 1 d . . .
H2c15a H 0.49813 0.886113 0.078802 Uiso 0.0277 2 1 d . . .
H1c43a H 0.827377 0.977498 0.158597 Uiso 0.0352 2 1 d . . .
H1c19b H -0.448891 0.638026 0.322057 Uiso 0.0371 2 1 d . . .
H1c24a H 0.195344 0.47457 0.109189 Uiso 0.0371 2 1 d . . .
H1c32b H 0.108548 0.5242 0.414741 Uiso 0.0408 2 1 d . . .
H1c24b H 0.360393 1.061411 0.356704 Uiso 0.0284 2 1 d . . .
H1c37a H 0.637451 0.718598 0.219807 Uiso 0.0268 2 1 d . . .
H2c37a H 0.672244 0.854044 0.223779 Uiso 0.0268 2 1 d . . .
H1c8b H -0.162927 0.274378 0.127655 Uiso 0.0346 2 1 d . . .
H1c30b H 0.453047 0.684936 0.399699 Uiso 0.0278 2 1 d . . .
H2c30b H 0.324239 0.59218 0.362181 Uiso 0.0278 2 1 d . . .
H1c9a H 0.688516 1.374954 0.355494 Uiso 0.0366 2 1 d . . .
H1c42a H 1.02679 1.014216 0.128899 Uiso 0.0411 2 1 d . . .
H1c32a H 0.592641 0.517704 0.050157 Uiso 0.0343 2 1 d . . .
H1c34b H 0.196613 0.417238 0.557909 Uiso 0.0542 2 1 d . . .
H1c18a H 0.261235 0.977374 -0.080803 Uiso 0.0421 2 1 d . . .
H1c40b H 0.786936 1.111829 0.39284 Uiso 0.0399 2 1 d . . .
H1c28b H -0.02364 1.009449 0.334714 Uiso 0.0359 2 1 d . . .
H1c21a H 0.323778 0.986492 0.108243 Uiso 0.0359 2 1 d . . .
H1c35b H 0.42544 0.523346 0.556255 Uiso 0.0507 2 1 d . . .
H1c25b H 0.433385 1.253217 0.407396 Uiso 0.0341 2 1 d . . .
H1c27b H 0.049646 1.201608 0.385489 Uiso 0.0423 2 1 d . . .
H1c33a H 0.571007 0.324835 0.062344 Uiso 0.0427 2 1 d . . .
H1c9b H -0.020908 0.185353 0.119544 Uiso 0.0354 2 1 d . . .
H1c26b H 0.27833 1.323586 0.423154 Uiso 0.0381 2 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl12a N3a . . 3.3246(17) ?
Cl13b N3b . . 3.3664(17) ?
P1a O2a . . 1.4793(11) ?
P1a N29a . . 1.6464(17) ?
P1a N14a . . 1.6376(14) ?
P1a N3a . . 1.6914(13) ?
P1b O2b . . 1.4798(11) ?
P1b N3b . . 1.6950(13) ?
P1b N29b . . 1.6428(14) ?
P1b N14b . . 1.6427(17) ?
O5b C4b . . 1.217(2) ?
O5a C4a . . 1.214(2) ?
N3b C4b . . 1.3604(17) ?
N3b H1n3b . . 0.81(2) ?
N29b C37b . . 1.4859(18) ?
N29b C30b . . 1.474(3) ?
N29a C30a . . 1.472(2) ?
N29a C37a . . 1.487(2) ?
N14a C22a . . 1.4834(17) ?
N14a C15a . . 1.473(2) ?
N14b C15b . . 1.478(2) ?
N14b C22b . . 1.475(2) ?
N3a C4a . . 1.3697(18) ?
N3a H1n3a . . 0.86(2) ?
C31b C36b . . 1.387(3) ?
C31b C32b . . 1.390(3) ?
C31b C30b . . 1.516(2) ?
C4b C6b . . 1.517(2) ?
C23a C22a . . 1.508(2) ?
C23a C28a . . 1.392(2) ?
C23a C24a . . 1.391(3) ?
C11a C6a . . 1.392(2) ?
C11a C10a . . 1.385(2) ?
C16a C17a . . 1.388(2) ?
C16a C15a . . 1.508(3) ?
C16a C21a . . 1.392(3) ?
C42b C41b . . 1.383(2) ?
C42b C43b . . 1.396(2) ?
C42b H1c42b . . 0.96 ?
C8a C7a . . 1.387(2) ?
C8a C9a . . 1.382(2) ?
C8a H1c8a . . 0.96 ?
C7b C6b . . 1.391(2) ?
C7b C8b . . 1.388(2) ?
C11b C6b . . 1.392(3) ?
C11b C10b . . 1.386(2) ?
C20a C19a . . 1.387(3) ?
C20a C21a . . 1.385(3) ?
C20a H1c20a . . 0.96 ?
C4a C6a . . 1.514(2) ?
C38b C37b . . 1.520(2) ?
C38b C39b . . 1.393(2) ?
C38b C43b . . 1.387(2) ?
C30a C31a . . 1.513(2) ?
C30a H1c30a . . 0.96 ?
C30a H2c30a . . 0.96 ?
C34a C35a . . 1.384(3) ?
C34a C33a . . 1.381(3) ?
C34a H1c34a . . 0.96 ?
C20b C21b . . 1.382(3) ?
C20b C19b . . 1.386(3) ?
C20b H1c20b . . 0.96 ?
C17b C16b . . 1.388(3) ?
C17b C18b . . 1.388(3) ?
C17b H1c17b . . 0.96 ?
C6a C7a . . 1.390(3) ?
C41b C40b . . 1.384(3) ?
C41b H1c41b . . 0.96 ?
C37b H1c37b . . 0.96 ?
C37b H2c37b . . 0.96 ?
C15b C16b . . 1.513(2) ?
C15b H1c15b . . 0.96 ?
C15b H2c15b . . 0.96 ?
C16b C21b . . 1.3926(19) ?
C35a C36a . . 1.395(3) ?
C35a H1c35a . . 0.96 ?
C17a C18a . . 1.389(3) ?
C17a H1c17a . . 0.96 ?
C21b H1c21b . . 0.96 ?
C41a C40a . . 1.382(2) ?
C41a C42a . . 1.383(3) ?
C41a H1c41a . . 0.96 ?
C40a C39a . . 1.384(3) ?
C40a H1c40a . . 0.96 ?
C26a C25a . . 1.385(3) ?
C26a C27a . . 1.377(3) ?
C26a H1c26a . . 0.96 ?
C22a H1c22a . . 0.96 ?
C22a H2c22a . . 0.96 ?
C10b C9b . . 1.382(2) ?
C10b H1c10b . . 0.96 ?
C39b C40b . . 1.392(2) ?
C39b H1c39b . . 0.96 ?
C36b C35b . . 1.392(3) ?
C36b H1c36b . . 0.96 ?
C18b C19b . . 1.388(2) ?
C18b H1c18b . . 0.96 ?
C39a C38a . . 1.389(3) ?
C39a H1c39a . . 0.96 ?
C36a C31a . . 1.388(2) ?
C36a H1c36a . . 0.96 ?
C38a C43a . . 1.385(2) ?
C38a C37a . . 1.511(3) ?
C22b C23b . . 1.519(2) ?
C22b H1c22b . . 0.96 ?
C22b H2c22b . . 0.96 ?
C23b C24b . . 1.391(2) ?
C23b C28b . . 1.390(3) ?
C31a C32a . . 1.388(3) ?
C25a C24a . . 1.390(3) ?
C25a H1c25a . . 0.96 ?
C28a C27a . . 1.389(3) ?
C28a H1c28a . . 0.96 ?
C43b H1c43b . . 0.96 ?
C10a C9a . . 1.383(3) ?
C10a H1c10a . . 0.96 ?
C19a C18a . . 1.381(3) ?
C19a H1c19a . . 0.96 ?
C33b C32b . . 1.393(3) ?
C33b C34b . . 1.387(3) ?
C33b H1c33b . . 0.96 ?
C27a H1c27a . . 0.96 ?
C15a H1c15a . . 0.96 ?
C15a H2c15a . . 0.96 ?
C43a C42a . . 1.390(3) ?
C43a H1c43a . . 0.96 ?
C19b H1c19b . . 0.96 ?
C24a H1c24a . . 0.96 ?
C32b H1c32b . . 0.96 ?
C24b C25b . . 1.386(2) ?
C24b H1c24b . . 0.96 ?
C37a H1c37a . . 0.96 ?
C37a H2c37a . . 0.96 ?
C8b C9b . . 1.382(3) ?
C8b H1c8b . . 0.96 ?
C30b H1c30b . . 0.96 ?
C30b H2c30b . . 0.96 ?
C9a H1c9a . . 0.96 ?
C42a H1c42a . . 0.96 ?
C32a C33a . . 1.388(3) ?
C32a H1c32a . . 0.96 ?
C34b C35b . . 1.378(3) ?
C34b H1c34b . . 0.96 ?
C18a H1c18a . . 0.96 ?
C40b H1c40b . . 0.96 ?
C28b C27b . . 1.389(2) ?
C28b H1c28b . . 0.96 ?
C21a H1c21a . . 0.96 ?
C35b H1c35b . . 0.96 ?
C25b C26b . . 1.387(3) ?
C25b H1c25b . . 0.96 ?
C27b C26b . . 1.386(2) ?
C27b H1c27b . . 0.96 ?
C33a H1c33a . . 0.96 ?
C9b H1c9b . . 0.96 ?
C26b H1c26b . . 0.96 ?

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2a P1a N29a . . . 118.36(8) ?
O2a P1a N14a . . . 110.74(6) ?
O2a P1a N3a . . . 105.14(7) ?
N29a P1a N14a . . . 106.27(7) ?
N29a P1a N3a . . . 104.64(6) ?
N14a P1a N3a . . . 111.58(7) ?
O2b P1b N3b . . . 104.65(7) ?
O2b P1b N29b . . . 118.32(6) ?
O2b P1b N14b . . . 110.32(7) ?
N3b P1b N29b . . . 106.06(7) ?
N3b P1b N14b . . . 112.89(7) ?
N29b P1b N14b . . . 104.76(8) ?
Cl13b N3b P1b . . . 132.22(7) ?
Cl13b N3b C4b . . . 65.64(10) ?
Cl13b N3b H1n3b . . . 79.3(16) ?
P1b N3b C4b . . . 128.11(13) ?
P1b N3b H1n3b . . . 114.4(12) ?
C4b N3b H1n3b . . . 117.1(11) ?
P1b N29b C37b . . . 116.32(11) ?
P1b N29b C30b . . . 126.17(11) ?
C37b N29b C30b . . . 113.96(13) ?
P1a N29a C30a . . . 118.82(10) ?
P1a N29a C37a . . . 119.71(12) ?
C30a N29a C37a . . . 115.86(15) ?
P1a N14a C22a . . . 119.70(10) ?
P1a N14a C15a . . . 123.70(10) ?
C22a N14a C15a . . . 114.44(12) ?
P1b N14b C15b . . . 124.06(12) ?
P1b N14b C22b . . . 119.91(11) ?
C15b N14b C22b . . . 115.41(15) ?
Cl12a N3a P1a . . . 128.54(7) ?
Cl12a N3a C4a . . . 68.02(10) ?
Cl12a N3a H1n3a . . . 72.2(15) ?
P1a N3a C4a . . . 127.92(12) ?
P1a N3a H1n3a . . . 114.7(11) ?
C4a N3a H1n3a . . . 117.4(11) ?
C36b C31b C32b . . . 118.70(17) ?
C36b C31b C30b . . . 119.83(16) ?
C32b C31b C30b . . . 121.38(16) ?
O5b C4b N3b . . . 124.00(14) ?
O5b C4b C6b . . . 120.68(12) ?
N3b C4b C6b . . . 115.32(14) ?
C22a C23a C28a . . . 120.83(17) ?
C22a C23a C24a . . . 120.22(16) ?
C28a C23a C24a . . . 118.95(17) ?
C6a C11a C10a . . . 122.34(19) ?
C17a C16a C15a . . . 120.22(17) ?
C17a C16a C21a . . . 118.62(18) ?
C15a C16a C21a . . . 121.13(15) ?
C41b C42b C43b . . . 119.54(17) ?
C41b C42b H1c42b . . . 120.23 ?
C43b C42b H1c42b . . . 120.23 ?
C7a C8a C9a . . . 119.0(2) ?
C7a C8a H1c8a . . . 120.5 ?
C9a C8a H1c8a . . . 120.5 ?
C6b C7b C8b . . . 122.25(19) ?
C6b C11b C10b . . . 122.42(15) ?
C19a C20a C21a . . . 120.4(2) ?
C19a C20a H1c20a . . . 119.78 ?
C21a C20a H1c20a . . . 119.78 ?
O5a C4a N3a . . . 124.63(14) ?
O5a C4a C6a . . . 120.39(12) ?
N3a C4a C6a . . . 114.98(14) ?
C37b C38b C39b . . . 121.48(15) ?
C37b C38b C43b . . . 120.01(14) ?
C39b C38b C43b . . . 118.51(15) ?
N29a C30a C31a . . . 117.20(14) ?
N29a C30a H1c30a . . . 109.47 ?
N29a C30a H2c30a . . . 109.47 ?
C31a C30a H1c30a . . . 109.47 ?
C31a C30a H2c30a . . . 109.47 ?
H1c30a C30a H2c30a . . . 100.45 ?
C35a C34a C33a . . . 119.54(19) ?
C35a C34a H1c34a . . . 120.23 ?
C33a C34a H1c34a . . . 120.23 ?
C21b C20b C19b . . . 120.50(14) ?
C21b C20b H1c20b . . . 119.75 ?
C19b C20b H1c20b . . . 119.75 ?
C16b C17b C18b . . . 121.26(14) ?
C16b C17b H1c17b . . . 119.37 ?
C18b C17b H1c17b . . . 119.37 ?
C11a C6a C4a . . . 120.28(17) ?
C11a C6a C7a . . . 116.99(14) ?
C4a C6a C7a . . . 122.58(13) ?
C42b C41b C40b . . . 119.65(16) ?
C42b C41b H1c41b . . . 120.17 ?
C40b C41b H1c41b . . . 120.17 ?
C8a C7a C6a . . . 122.03(15) ?
N29b C37b C38b . . . 114.35(15) ?
N29b C37b H1c37b . . . 109.47 ?
N29b C37b H2c37b . . . 109.47 ?
C38b C37b H1c37b . . . 109.47 ?
C38b C37b H2c37b . . . 109.47 ?
H1c37b C37b H2c37b . . . 104.1 ?
N14b C15b C16b . . . 112.87(13) ?
N14b C15b H1c15b . . . 109.47 ?
N14b C15b H2c15b . . . 109.47 ?
C16b C15b H1c15b . . . 109.47 ?
C16b C15b H2c15b . . . 109.47 ?
H1c15b C15b H2c15b . . . 105.84 ?
C17b C16b C15b . . . 120.40(12) ?
C17b C16b C21b . . . 118.37(16) ?
C15b C16b C21b . . . 121.22(17) ?
C4b C6b C7b . . . 120.99(17) ?
C4b C6b C11b . . . 122.21(14) ?
C7b C6b C11b . . . 116.74(15) ?
C34a C35a C36a . . . 120.26(18) ?
C34a C35a H1c35a . . . 119.87 ?
C36a C35a H1c35a . . . 119.87 ?
C16a C17a C18a . . . 120.86(19) ?
C16a C17a H1c17a . . . 119.57 ?
C18a C17a H1c17a . . . 119.57 ?
C20b C21b C16b . . . 120.66(18) ?
C20b C21b H1c21b . . . 119.67 ?
C16b C21b H1c21b . . . 119.67 ?
C40a C41a C42a . . . 119.27(19) ?
C40a C41a H1c41a . . . 120.36 ?
C42a C41a H1c41a . . . 120.37 ?
C41a C40a C39a . . . 120.0(2) ?
C41a C40a H1c40a . . . 119.98 ?
C39a C40a H1c40a . . . 119.98 ?
C25a C26a C27a . . . 119.74(19) ?
C25a C26a H1c26a . . . 120.13 ?
C27a C26a H1c26a . . . 120.13 ?
N14a C22a C23a . . . 112.67(15) ?
N14a C22a H1c22a . . . 109.47 ?
N14a C22a H2c22a . . . 109.47 ?
C23a C22a H1c22a . . . 109.47 ?
C23a C22a H2c22a . . . 109.47 ?
H1c22a C22a H2c22a . . . 106.07 ?
C11b C10b C9b . . . 118.8(2) ?
C11b C10b H1c10b . . . 120.59 ?
C9b C10b H1c10b . . . 120.59 ?
C38b C39b C40b . . . 120.21(17) ?
C38b C39b H1c39b . . . 119.89 ?
C40b C39b H1c39b . . . 119.89 ?
C31b C36b C35b . . . 120.94(19) ?
C31b C36b H1c36b . . . 119.53 ?
C35b C36b H1c36b . . . 119.53 ?
C17b C18b C19b . . . 119.7(2) ?
C17b C18b H1c18b . . . 120.17 ?
C19b C18b H1c18b . . . 120.17 ?
C40a C39a C38a . . . 121.04(16) ?
C40a C39a H1c39a . . . 119.48 ?
C38a C39a H1c39a . . . 119.48 ?
C35a C36a C31a . . . 120.31(18) ?
C35a C36a H1c36a . . . 119.84 ?
C31a C36a H1c36a . . . 119.84 ?
C39a C38a C43a . . . 118.79(17) ?
C39a C38a C37a . . . 119.99(14) ?
C43a C38a C37a . . . 121.21(18) ?
N14b C22b C23b . . . 113.47(13) ?
N14b C22b H1c22b . . . 109.47 ?
N14b C22b H2c22b . . . 109.47 ?
C23b C22b H1c22b . . . 109.47 ?
C23b C22b H2c22b . . . 109.47 ?
H1c22b C22b H2c22b . . . 105.15 ?
C22b C23b C24b . . . 120.48(18) ?
C22b C23b C28b . . . 120.93(13) ?
C24b C23b C28b . . . 118.56(15) ?
C30a C31a C36a . . . 123.32(17) ?
C30a C31a C32a . . . 117.80(15) ?
C36a C31a C32a . . . 118.85(17) ?
C26a C25a C24a . . . 120.3(2) ?
C26a C25a H1c25a . . . 119.85 ?
C24a C25a H1c25a . . . 119.85 ?
C23a C28a C27a . . . 120.44(18) ?
C23a C28a H1c28a . . . 119.78 ?
C27a C28a H1c28a . . . 119.78 ?
C42b C43b C38b . . . 121.37(15) ?
C42b C43b H1c43b . . . 119.31 ?
C38b C43b H1c43b . . . 119.32 ?
C11a C10a C9a . . . 118.77(15) ?
C11a C10a H1c10a . . . 120.61 ?
C9a C10a H1c10a . . . 120.61 ?
C20a C19a C18a . . . 119.4(2) ?
C20a C19a H1c19a . . . 120.29 ?
C18a C19a H1c19a . . . 120.28 ?
C32b C33b C34b . . . 120.2(2) ?
C32b C33b H1c33b . . . 119.91 ?
C34b C33b H1c33b . . . 119.91 ?
C26a C27a C28a . . . 120.32(18) ?
C26a C27a H1c27a . . . 119.84 ?
C28a C27a H1c27a . . . 119.84 ?
N14a C15a C16a . . . 113.29(16) ?
N14a C15a H1c15a . . . 109.47 ?
N14a C15a H2c15a . . . 109.47 ?
C16a C15a H1c15a . . . 109.47 ?
C16a C15a H2c15a . . . 109.47 ?
H1c15a C15a H2c15a . . . 105.36 ?
C38a C43a C42a . . . 120.1(2) ?
C38a C43a H1c43a . . . 119.96 ?
C42a C43a H1c43a . . . 119.96 ?
C20b C19b C18b . . . 119.51(17) ?
C20b C19b H1c19b . . . 120.24 ?
C18b C19b H1c19b . . . 120.24 ?
C23a C24a C25a . . . 120.26(18) ?
C23a C24a H1c24a . . . 119.87 ?
C25a C24a H1c24a . . . 119.87 ?
C31b C32b C33b . . . 120.46(19) ?
C31b C32b H1c32b . . . 119.77 ?
C33b C32b H1c32b . . . 119.77 ?
C23b C24b C25b . . . 120.72(19) ?
C23b C24b H1c24b . . . 119.64 ?
C25b C24b H1c24b . . . 119.64 ?
N29a C37a C38a . . . 112.48(13) ?
N29a C37a H1c37a . . . 109.47 ?
N29a C37a H2c37a . . . 109.47 ?
C38a C37a H1c37a . . . 109.47 ?
C38a C37a H2c37a . . . 109.47 ?
H1c37a C37a H2c37a . . . 106.29 ?
C7b C8b C9b . . . 118.91(16) ?
C7b C8b H1c8b . . . 120.54 ?
C9b C8b H1c8b . . . 120.54 ?
N29b C30b C31b . . . 114.07(16) ?
N29b C30b H1c30b . . . 109.47 ?
N29b C30b H2c30b . . . 109.47 ?
C31b C30b H1c30b . . . 109.47 ?
C31b C30b H2c30b . . . 109.47 ?
H1c30b C30b H2c30b . . . 104.44 ?
C8a C9a C10a . . . 120.87(16) ?
C8a C9a H1c9a . . . 119.56 ?
C10a C9a H1c9a . . . 119.56 ?
C41a C42a C43a . . . 120.76(17) ?
C41a C42a H1c42a . . . 119.62 ?
C43a C42a H1c42a . . . 119.62 ?
C31a C32a C33a . . . 120.74(18) ?
C31a C32a H1c32a . . . 119.63 ?
C33a C32a H1c32a . . . 119.63 ?
C33b C34b C35b . . . 119.7(2) ?
C33b C34b H1c34b . . . 120.15 ?
C35b C34b H1c34b . . . 120.15 ?
C17a C18a C19a . . . 120.14(19) ?
C17a C18a H1c18a . . . 119.93 ?
C19a C18a H1c18a . . . 119.93 ?
C41b C40b C39b . . . 120.70(17) ?
C41b C40b H1c40b . . . 119.65 ?
C39b C40b H1c40b . . . 119.65 ?
C23b C28b C27b . . . 120.75(15) ?
C23b C28b H1c28b . . . 119.63 ?
C27b C28b H1c28b . . . 119.63 ?
C16a C21a C20a . . . 120.49(18) ?
C16a C21a H1c21a . . . 119.75 ?
C20a C21a H1c21a . . . 119.75 ?
C36b C35b C34b . . . 120.0(2) ?
C36b C35b H1c35b . . . 119.99 ?
C34b C35b H1c35b . . . 119.99 ?
C24b C25b C26b . . . 120.48(15) ?
C24b C25b H1c25b . . . 119.76 ?
C26b C25b H1c25b . . . 119.76 ?
C28b C27b C26b . . . 120.3(2) ?
C28b C27b H1c27b . . . 119.83 ?
C26b C27b H1c27b . . . 119.83 ?
C34a C33a C32a . . . 120.3(2) ?
C34a C33a H1c33a . . . 119.87 ?
C32a C33a H1c33a . . . 119.88 ?
C10b C9b C8b . . . 120.81(16) ?
C10b C9b H1c9b . . . 119.59 ?
C8b C9b H1c9b . . . 119.59 ?
C25b C26b C27b . . . 119.14(16) ?
C25b C26b H1c26b . . . 120.43 ?
C27b C26b H1c26b . . . 120.43 ?

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
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3a H1n3a O2b . . . 0.86(2) 1.94(2) 2.7980(19) 174.2(18) ?
N3b H1n3b O2a . . . 0.81(2) 1.95(2) 2.7659(19) 178.5(15) ?
C21b H1c21b O5b . . . 0.96 2.46 3.292(3) 145.11 ?
C22a H2c22a O2a . . . 0.96 2.45 2.900(2) 108.15 ?
C22b H2c22b O2b . . . 0.96 2.49 2.926(2) 107.28 ?
C15a H2c15a O5a . . . 0.96 2.38 3.1033(16) 131.75 ?
C32b H1c32b O5b . . . 0.96 2.32 3.167(2) 146.78 ?
_database_code_depnum_ccdc_archive 'CCDC 961006'
