# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ty001dia2
_database_code_depnum_ccdc_archive 'CCDC 1441553'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'Diethyl (1-((1-(4-aminophenyl)ethoxy)(tert-butyl)amino)-2,2-dimethylpropyl)phosphonate '
_chemical_formula_moiety         '2(C21 H39 N2 O4 P)'
_chemical_formula_sum            'C42 H78 N4 O8 P2'
_chemical_formula_weight         829.02
_chemical_melting_point          110
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0189(3)
_cell_length_b                   13.8383(3)
_cell_length_c                   19.9173(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.1629(16)
_cell_angle_gamma                90
_cell_volume                     4958.84(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9480
_cell_measurement_theta_min      4.0030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1808
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19407
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.044
_diffrn_reflns_theta_min         3.892
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   87.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5600   38.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega   95.00  175.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  124.0000  174.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  149.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   67.00  149.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  178.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  125.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  178.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega   65.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   30.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   22.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -45.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 11 omega -122.00  -51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600 -178.0000  150.0000 71

#__ type_ start__ end____ width___ exp.time_
 12 omega -122.00   -6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600  -77.0000   90.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0071067000
_diffrn_orient_matrix_UB_12      -0.0775732000
_diffrn_orient_matrix_UB_13      -0.0554894000
_diffrn_orient_matrix_UB_21      0.0032421000
_diffrn_orient_matrix_UB_22      0.0793095000
_diffrn_orient_matrix_UB_23      -0.0540249000
_diffrn_orient_matrix_UB_31      0.0852573000
_diffrn_orient_matrix_UB_32      -0.0094951000
_diffrn_orient_matrix_UB_33      0.0017268000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7140
_reflns_number_total             9194
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9194
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1053P)²+1.5358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1972
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C21
 1.4 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Rotating group:
 N2(H2A,H2B), N4(H4A,H4B)
4.b Ternary CH refined with riding coordinates:
 C1(H1), C13(H13), C22(H22), C34(H34)
4.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C39(H39A,H39B), C41(H41A,H41B)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C24(H24), C25(H25), C27(H27), C28(H28)
4.e Idealised Me refined with riding coordinates:
 C21(H21A,H21B,H21C)
4.f Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.81078(4) 0.73837(6) 0.39812(4) 0.0625(2) Uani 1 1 d . . . . .
O1 O 0.91024(8) 0.68274(12) 0.30878(9) 0.0484(4) Uani 1 1 d . . . . .
O2 O 0.82670(14) 0.6488(2) 0.43429(12) 0.0884(7) Uani 1 1 d . . . . .
O3 O 0.87268(13) 0.81693(17) 0.40827(13) 0.0799(6) Uani 1 1 d . . . . .
O4 O 0.74182(14) 0.7958(3) 0.42304(12) 0.1009(9) Uani 1 1 d . . . . .
N1 N 0.84558(10) 0.70921(14) 0.26501(10) 0.0462(4) Uani 1 1 d . . . . .
N2 N 1.19254(12) 0.5207(2) 0.47302(13) 0.0653(6) Uani 1 1 d . . . . .
H2A H 1.2103 0.5752 0.4872 0.078 Uiso 1 1 d GR . . . .
H2B H 1.1837 0.4847 0.5069 0.078 Uiso 1 1 d GR . . . .
C1 C 0.92374(13) 0.57941(18) 0.31059(14) 0.0535(6) Uani 1 1 d . . . . .
H1 H 0.8830 0.5481 0.3330 0.064 Uiso 1 1 calc R . . . .
C2 C 0.99473(12) 0.56700(18) 0.35431(13) 0.0490(5) Uani 1 1 d . . . . .
C3 C 0.99990(13) 0.49471(18) 0.40173(13) 0.0515(5) Uani 1 1 d . . . . .
H3 H 0.9589 0.4554 0.4076 0.062 Uiso 1 1 calc R . . . .
C4 C 1.06456(13) 0.47889(19) 0.44096(12) 0.0522(5) Uani 1 1 d . . . . .
H4 H 1.0665 0.4286 0.4720 0.063 Uiso 1 1 calc R . . . .
C5 C 1.12619(12) 0.53687(18) 0.43466(12) 0.0494(5) Uani 1 1 d . . . . .
C6 C 1.12146(14) 0.6091(2) 0.38599(17) 0.0668(7) Uani 1 1 d . . . . .
H6 H 1.1624 0.6484 0.3800 0.080 Uiso 1 1 calc R . . . .
C7 C 1.05714(14) 0.6234(2) 0.34648(16) 0.0654(7) Uani 1 1 d . . . . .
H7 H 1.0556 0.6717 0.3140 0.078 Uiso 1 1 calc R . . . .
C8 C 0.9294(2) 0.5344(3) 0.24216(19) 0.0824(10) Uani 1 1 d . . . . .
H8A H 0.8856 0.5498 0.2145 0.124 Uiso 1 1 calc GR . . . .
H8B H 0.9336 0.4656 0.2467 0.124 Uiso 1 1 calc GR . . . .
H8C H 0.9724 0.5592 0.2217 0.124 Uiso 1 1 calc GR . . . .
C9 C 0.87103(14) 0.7932(2) 0.22384(16) 0.0621(7) Uani 1 1 d . . . . .
C10 C 0.8974(2) 0.8798(3) 0.2649(2) 0.0900(11) Uani 1 1 d . . . . .
H10A H 0.8583 0.9013 0.2921 0.135 Uiso 1 1 calc GR . . . .
H10B H 0.9107 0.9309 0.2352 0.135 Uiso 1 1 calc GR . . . .
H10C H 0.9400 0.8620 0.2933 0.135 Uiso 1 1 calc GR . . . .
C11 C 0.9334(2) 0.7568(4) 0.1821(2) 0.1101(17) Uani 1 1 d . . . . .
H11A H 0.9760 0.7414 0.2112 0.165 Uiso 1 1 calc GR . . . .
H11B H 0.9464 0.8060 0.1509 0.165 Uiso 1 1 calc GR . . . .
H11C H 0.9172 0.7000 0.1578 0.165 Uiso 1 1 calc GR . . . .
C12 C 0.80730(18) 0.8256(3) 0.17537(18) 0.0809(10) Uani 1 1 d . . . . .
H12A H 0.7886 0.7711 0.1499 0.121 Uiso 1 1 calc GR . . . .
H12B H 0.8250 0.8736 0.1453 0.121 Uiso 1 1 calc GR . . . .
H12C H 0.7682 0.8525 0.2004 0.121 Uiso 1 1 calc GR . . . .
C13 C 0.78247(12) 0.72897(17) 0.30805(12) 0.0451(5) Uani 1 1 d . . . . .
H13 H 0.7638 0.7931 0.2947 0.054 Uiso 1 1 calc R . . . .
C14 C 0.71568(13) 0.6570(2) 0.29284(15) 0.0583(6) Uani 1 1 d . . . . .
C15 C 0.73375(18) 0.5533(2) 0.3132(2) 0.0819(10) Uani 1 1 d . . . . .
H15A H 0.7741 0.5302 0.2881 0.123 Uiso 1 1 calc GR . . . .
H15B H 0.6908 0.5134 0.3039 0.123 Uiso 1 1 calc GR . . . .
H15C H 0.7477 0.5509 0.3604 0.123 Uiso 1 1 calc GR . . . .
C16 C 0.64653(17) 0.6894(3) 0.3284(3) 0.1038(14) Uani 1 1 d . . . . .
H16A H 0.6560 0.6845 0.3762 0.156 Uiso 1 1 calc GR . . . .
H16B H 0.6052 0.6488 0.3147 0.156 Uiso 1 1 calc GR . . . .
H16C H 0.6351 0.7552 0.3167 0.156 Uiso 1 1 calc GR . . . .
C17 C 0.6952(2) 0.6565(3) 0.2178(2) 0.0914(12) Uani 1 1 d . . . . .
H17A H 0.6777 0.7194 0.2041 0.137 Uiso 1 1 calc GR . . . .
H17B H 0.6568 0.6097 0.2081 0.137 Uiso 1 1 calc GR . . . .
H17C H 0.7382 0.6401 0.1937 0.137 Uiso 1 1 calc GR . . . .
C18 C 0.9455(3) 0.7955(5) 0.4387(4) 0.169(2) Uani 1 1 d . U . . .
H18A H 0.9436 0.7368 0.4653 0.203 Uiso 1 1 calc R . . . .
H18B H 0.9805 0.7855 0.4040 0.203 Uiso 1 1 calc R . . . .
C19 C 0.9686(4) 0.8728(6) 0.4797(4) 0.181(2) Uani 1 1 d . U . . .
H19A H 0.9654 0.9316 0.4542 0.271 Uiso 1 1 calc GR . . . .
H19B H 1.0191 0.8626 0.4961 0.271 Uiso 1 1 calc GR . . . .
H19C H 0.9372 0.8773 0.5170 0.271 Uiso 1 1 calc GR . . . .
C20 C 0.7368(4) 0.8012(9) 0.4944(3) 0.232(6) Uani 1 1 d D . . . .
H20A H 0.7335 0.7360 0.5119 0.279 Uiso 1 1 calc R . . . .
H20B H 0.7824 0.8295 0.5137 0.279 Uiso 1 1 calc R . . . .
C21 C 0.6769(5) 0.8545(8) 0.5163(3) 0.230(5) Uani 1 1 d D . . . .
H21A H 0.6717 0.9131 0.4906 0.345 Uiso 1 1 calc R . . . .
H21B H 0.6856 0.8701 0.5631 0.345 Uiso 1 1 calc R . . . .
H21C H 0.6322 0.8170 0.5103 0.345 Uiso 1 1 calc R . . . .
P2 P 0.30761(4) 0.79627(5) 0.53201(3) 0.0560(2) Uani 1 1 d . . . . .
O5 O 0.39951(8) 0.77253(11) 0.64345(8) 0.0450(3) Uani 1 1 d . . . . .
O6 O 0.30611(12) 0.69188(15) 0.52115(10) 0.0676(5) Uani 1 1 d . . . . .
O7 O 0.38121(12) 0.84545(17) 0.51210(10) 0.0711(5) Uani 1 1 d . . . . .
O8 O 0.24965(14) 0.8553(2) 0.48587(12) 0.0872(7) Uani 1 1 d . . . . .
N3 N 0.34143(11) 0.83402(14) 0.66821(10) 0.0494(5) Uani 1 1 d . . . . .
N4 N 0.64392(17) 0.4743(3) 0.5686(2) 0.1149(14) Uani 1 1 d . . . . .
H4A H 0.6288 0.4354 0.5369 0.138 Uiso 1 1 d GR . . . .
H4B H 0.6759 0.5139 0.5534 0.138 Uiso 1 1 d GR . . . .
C22 C 0.39829(13) 0.67510(17) 0.67018(12) 0.0461(5) Uani 1 1 d . . . . .
H22 H 0.3523 0.6435 0.6533 0.055 Uiso 1 1 calc R . . . .
C23 C 0.46296(12) 0.62484(17) 0.64070(11) 0.0454(5) Uani 1 1 d . . . . .
C24 C 0.45302(14) 0.53969(18) 0.60555(13) 0.0519(5) Uani 1 1 d . . . . .
H24 H 0.4052 0.5152 0.5981 0.062 Uiso 1 1 calc R . . . .
C25 C 0.51201(16) 0.4899(2) 0.58120(15) 0.0638(7) Uani 1 1 d . . . . .
H25 H 0.5036 0.4319 0.5585 0.077 Uiso 1 1 calc R . . . .
C26 C 0.58381(15) 0.5254(2) 0.59010(15) 0.0655(7) Uani 1 1 d . . . . .
C27 C 0.59398(14) 0.6131(2) 0.62325(15) 0.0622(7) Uani 1 1 d . . . . .
H27 H 0.6412 0.6401 0.6279 0.075 Uiso 1 1 calc R . . . .
C28 C 0.53479(13) 0.66062(19) 0.64935(14) 0.0557(6) Uani 1 1 d . . . . .
H28 H 0.5432 0.7177 0.6732 0.067 Uiso 1 1 calc R . . . .
C29 C 0.40246(18) 0.6707(2) 0.74646(14) 0.0654(7) Uani 1 1 d . . . . .
H29A H 0.4493 0.6965 0.7635 0.098 Uiso 1 1 calc GR . . . .
H29B H 0.3980 0.6048 0.7607 0.098 Uiso 1 1 calc GR . . . .
H29C H 0.3627 0.7082 0.7634 0.098 Uiso 1 1 calc GR . . . .
C30 C 0.37925(18) 0.9281(2) 0.68870(16) 0.0681(7) Uani 1 1 d . . . . .
C31 C 0.3212(3) 0.9960(3) 0.7160(2) 0.1022(14) Uani 1 1 d . . . . .
H31A H 0.2830 1.0085 0.6816 0.153 Uiso 1 1 calc GR . . . .
H31B H 0.3445 1.0557 0.7298 0.153 Uiso 1 1 calc GR . . . .
H31C H 0.2996 0.9664 0.7539 0.153 Uiso 1 1 calc GR . . . .
C32 C 0.4362(2) 0.9058(3) 0.7460(2) 0.0900(11) Uani 1 1 d . . . . .
H32A H 0.4117 0.8766 0.7825 0.135 Uiso 1 1 calc GR . . . .
H32B H 0.4598 0.9647 0.7612 0.135 Uiso 1 1 calc GR . . . .
H32C H 0.4730 0.8623 0.7304 0.135 Uiso 1 1 calc GR . . . .
C33 C 0.4174(3) 0.9772(3) 0.6319(3) 0.1098(15) Uani 1 1 d . . . . .
H33A H 0.4545 0.9349 0.6154 0.165 Uiso 1 1 calc GR . . . .
H33B H 0.4405 1.0358 0.6482 0.165 Uiso 1 1 calc GR . . . .
H33C H 0.3813 0.9921 0.5961 0.165 Uiso 1 1 calc GR . . . .
C34 C 0.28104(14) 0.84041(19) 0.61437(13) 0.0540(6) Uani 1 1 d . . . . .
H34 H 0.2717 0.9097 0.6081 0.065 Uiso 1 1 calc R . . . .
C35 C 0.20500(15) 0.7967(3) 0.63742(18) 0.0724(8) Uani 1 1 d . . . . .
C36 C 0.2090(2) 0.6881(3) 0.6501(3) 0.1085(15) Uani 1 1 d . . . . .
H36A H 0.2203 0.6555 0.6094 0.163 Uiso 1 1 calc GR . . . .
H36B H 0.1621 0.6657 0.6646 0.163 Uiso 1 1 calc GR . . . .
H36C H 0.2472 0.6747 0.6843 0.163 Uiso 1 1 calc GR . . . .
C37 C 0.1426(2) 0.8168(7) 0.5849(4) 0.208(5) Uani 1 1 d . . . . .
H37A H 0.1344 0.8852 0.5815 0.312 Uiso 1 1 calc GR . . . .
H37B H 0.0979 0.7857 0.5979 0.312 Uiso 1 1 calc GR . . . .
H37C H 0.1559 0.7921 0.5422 0.312 Uiso 1 1 calc GR . . . .
C38 C 0.1861(3) 0.8380(5) 0.7031(3) 0.153(3) Uani 1 1 d . . . . .
H38A H 0.2301 0.8413 0.7325 0.229 Uiso 1 1 calc GR . . . .
H38B H 0.1499 0.7976 0.7229 0.229 Uiso 1 1 calc GR . . . .
H38C H 0.1660 0.9017 0.6964 0.229 Uiso 1 1 calc GR . . . .
C39 C 0.4493(2) 0.7921(3) 0.50146(18) 0.0869(11) Uani 1 1 d . . . . .
H39A H 0.4434 0.7254 0.5152 0.104 Uiso 1 1 calc R . . . .
H39B H 0.4901 0.8200 0.5287 0.104 Uiso 1 1 calc R . . . .
C40 C 0.4660(4) 0.7956(5) 0.4308(3) 0.139(2) Uani 1 1 d . . . . .
H40A H 0.4259 0.7669 0.4040 0.209 Uiso 1 1 calc GR . . . .
H40B H 0.5111 0.7606 0.4244 0.209 Uiso 1 1 calc GR . . . .
H40C H 0.4721 0.8617 0.4174 0.209 Uiso 1 1 calc GR . . . .
C41 C 0.2503(4) 0.8468(4) 0.4139(2) 0.131(2) Uani 1 1 d . . . . .
H41A H 0.2959 0.8748 0.3989 0.157 Uiso 1 1 calc R . . . .
H41B H 0.2498 0.7789 0.4017 0.157 Uiso 1 1 calc R . . . .
C42 C 0.1901(5) 0.8924(7) 0.3814(3) 0.214(4) Uani 1 1 d . . . . .
H42A H 0.1449 0.8689 0.3989 0.321 Uiso 1 1 calc GR . . . .
H42B H 0.1898 0.8792 0.3341 0.321 Uiso 1 1 calc GR . . . .
H42C H 0.1938 0.9609 0.3887 0.321 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.454(3) . ?
P1 O3 1.563(2) . ?
P1 O4 1.578(3) . ?
P1 C13 1.842(2) . ?
O1 N1 1.463(2) . ?
O1 C1 1.451(3) . ?
O3 C18 1.446(5) . ?
O4 C20 1.432(6) . ?
N1 C9 1.509(3) . ?
N1 C13 1.487(3) . ?
N2 H2A 0.8605 . ?
N2 H2B 0.8609 . ?
N2 C5 1.401(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.517(3) . ?
C1 C8 1.507(4) . ?
C2 C3 1.375(4) . ?
C2 C7 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 C6 1.391(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.511(5) . ?
C9 C11 1.521(5) . ?
C9 C12 1.526(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.579(3) . ?
C14 C15 1.521(4) . ?
C14 C16 1.534(5) . ?
C14 C17 1.520(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.396(8) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.3978(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
P2 O6 1.461(2) . ?
P2 O7 1.561(2) . ?
P2 O8 1.580(2) . ?
P2 C34 1.839(3) . ?
O5 N3 1.456(2) . ?
O5 C22 1.450(3) . ?
O7 C39 1.457(4) . ?
O8 C41 1.438(5) . ?
N3 C30 1.515(3) . ?
N3 C34 1.488(3) . ?
N4 H4A 0.8616 . ?
N4 H4B 0.8617 . ?
N4 C26 1.381(4) . ?
C22 H22 0.9800 . ?
C22 C23 1.504(3) . ?
C22 C29 1.518(4) . ?
C23 C24 1.377(3) . ?
C23 C28 1.388(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.377(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.386(4) . ?
C26 C27 1.389(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(4) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.528(5) . ?
C30 C32 1.524(5) . ?
C30 C33 1.517(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34 0.9800 . ?
C34 C35 1.588(4) . ?
C35 C36 1.526(6) . ?
C35 C37 1.519(6) . ?
C35 C38 1.484(6) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.457(6) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.385(7) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 114.13(14) . . ?
O2 P1 O4 114.26(17) . . ?
O2 P1 C13 117.30(14) . . ?
O3 P1 O4 100.23(16) . . ?
O3 P1 C13 109.41(13) . . ?
O4 P1 C13 99.28(12) . . ?
C1 O1 N1 112.87(16) . . ?
C18 O3 P1 122.4(4) . . ?
C20 O4 P1 115.6(3) . . ?
O1 N1 C9 105.13(17) . . ?
O1 N1 C13 108.17(17) . . ?
C13 N1 C9 115.89(19) . . ?
H2A N2 H2B 109.4 . . ?
C5 N2 H2A 109.3 . . ?
C5 N2 H2B 109.3 . . ?
O1 C1 H1 108.5 . . ?
O1 C1 C2 105.12(19) . . ?
O1 C1 C8 113.8(2) . . ?
C2 C1 H1 108.5 . . ?
C8 C1 H1 108.5 . . ?
C8 C1 C2 112.1(2) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 C7 117.6(2) . . ?
C7 C2 C1 122.4(2) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N2 121.6(2) . . ?
C4 C5 C6 117.5(2) . . ?
C6 C5 N2 120.8(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.4 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 114.4(3) . . ?
N1 C9 C11 107.3(3) . . ?
N1 C9 C12 109.2(2) . . ?
C10 C9 C11 109.8(3) . . ?
C10 C9 C12 108.2(3) . . ?
C11 C9 C12 107.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 C13 H13 105.8 . . ?
N1 C13 P1 113.27(14) . . ?
N1 C13 H13 105.8 . . ?
N1 C13 C14 111.9(2) . . ?
C14 C13 P1 113.48(17) . . ?
C14 C13 H13 105.8 . . ?
C15 C14 C13 113.2(2) . . ?
C15 C14 C16 108.7(3) . . ?
C16 C14 C13 110.9(3) . . ?
C17 C14 C13 109.4(2) . . ?
C17 C14 C15 107.1(3) . . ?
C17 C14 C16 107.3(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.9 . . ?
O3 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 O3 108.8(5) . . ?
C19 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 108.4 . . ?
O4 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 O4 115.4(5) . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 P2 O7 113.74(13) . . ?
O6 P2 O8 114.77(14) . . ?
O6 P2 C34 117.19(13) . . ?
O7 P2 O8 99.81(14) . . ?
O7 P2 C34 110.40(12) . . ?
O8 P2 C34 98.68(13) . . ?
C22 O5 N3 113.16(16) . . ?
C39 O7 P2 123.4(2) . . ?
C41 O8 P2 119.7(3) . . ?
O5 N3 C30 105.80(19) . . ?
O5 N3 C34 107.55(17) . . ?
C34 N3 C30 116.3(2) . . ?
H4A N4 H4B 109.3 . . ?
C26 N4 H4A 109.0 . . ?
C26 N4 H4B 109.6 . . ?
O5 C22 H22 108.6 . . ?
O5 C22 C23 105.00(18) . . ?
O5 C22 C29 113.8(2) . . ?
C23 C22 H22 108.6 . . ?
C23 C22 C29 112.1(2) . . ?
C29 C22 H22 108.6 . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 C28 117.6(2) . . ?
C28 C23 C22 121.6(2) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 C23 121.7(2) . . ?
C25 C24 H24 119.1 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.7(3) . . ?
C26 C25 H25 119.6 . . ?
N4 C26 C25 121.4(3) . . ?
N4 C26 C27 120.6(3) . . ?
C25 C26 C27 117.9(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 H28 119.4 . . ?
C27 C28 C23 121.2(2) . . ?
C27 C28 H28 119.4 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 C31 108.5(3) . . ?
N3 C30 C32 107.6(2) . . ?
N3 C30 C33 113.6(3) . . ?
C32 C30 C31 107.6(3) . . ?
C33 C30 C31 109.7(3) . . ?
C33 C30 C32 109.6(3) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
P2 C34 H34 105.3 . . ?
N3 C34 P2 114.03(16) . . ?
N3 C34 H34 105.3 . . ?
N3 C34 C35 112.2(2) . . ?
C35 C34 P2 113.7(2) . . ?
C35 C34 H34 105.3 . . ?
C36 C35 C34 112.9(2) . . ?
C37 C35 C34 110.5(3) . . ?
C37 C35 C36 108.7(5) . . ?
C38 C35 C34 110.6(3) . . ?
C38 C35 C36 104.1(4) . . ?
C38 C35 C37 109.8(5) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O7 C39 H39A 109.6 . . ?
O7 C39 H39B 109.6 . . ?
O7 C39 C40 110.2(4) . . ?
H39A C39 H39B 108.1 . . ?
C40 C39 H39A 109.6 . . ?
C40 C39 H39B 109.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O8 C41 H41A 109.1 . . ?
O8 C41 H41B 109.1 . . ?
H41A C41 H41B 107.9 . . ?
C42 C41 O8 112.3(6) . . ?
C42 C41 H41A 109.1 . . ?
C42 C41 H41B 109.1 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/ethyl acetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sg1bame
_database_code_depnum_ccdc_archive 'CCDC 1441554'
_audit_update_record             
;
2015-12-10 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'Methyl 4-(1-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)ethyl)benzoate '
_chemical_formula_moiety         'C23 H40 N O6 P'
_chemical_formula_sum            'C23 H40 N O6 P'
_chemical_formula_weight         457.53
_chemical_melting_point          82-84
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.62323(15)
_cell_length_b                   9.53739(16)
_cell_length_c                   31.7545(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.2784(17)
_cell_angle_gamma                90
_cell_volume                     2611.56(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8026
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.6280
_cell_measurement_theta_min      4.8300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.938
_diffrn_reflns_theta_min         4.841
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -58.00   -2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.5127  125.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega  -60.00  -34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.5127  -59.0000 -158.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   95.00  142.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127  125.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   94.00  130.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127  125.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega  103.00  134.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127  125.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega   -9.00  152.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127    0.0000  -60.0000 161

#__ type_ start__ end____ width___ exp.time_
 12 omega   24.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127 -125.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 13 omega  104.00  139.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       54.5127  125.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 14 omega   68.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255   38.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
 15 omega  100.00  173.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  111.0000  120.0000 73

#__ type_ start__ end____ width___ exp.time_
 16 omega   31.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255 -111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00  135.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  178.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
 18 omega   25.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  -50.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255   63.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 20 omega   68.00  165.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255   63.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 21 omega   63.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  -38.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 22 omega   26.00   52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  -38.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  131.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255   12.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 24 omega  101.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  111.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 25 omega   86.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255 -111.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   23.00  154.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255  -91.0000   30.0000 131

#__ type_ start__ end____ width___ exp.time_
 27 omega   30.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      109.0255 -111.0000  -30.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1456583000
_diffrn_orient_matrix_UB_12      0.0934858000
_diffrn_orient_matrix_UB_13      0.0005177000
_diffrn_orient_matrix_UB_21      0.0734151000
_diffrn_orient_matrix_UB_22      0.0963731000
_diffrn_orient_matrix_UB_23      -0.0333392000
_diffrn_orient_matrix_UB_31      -0.0728186000
_diffrn_orient_matrix_UB_32      -0.0898145000
_diffrn_orient_matrix_UB_33      -0.0352476000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4211
_reflns_number_total             5003
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+1.1501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1558
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C17)
Uanis(C14) = Uanis(C15)
3. Others
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23)
4.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C9(H9A,
 H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.70601(7) 0.42959(7) 0.35337(2) 0.05792(19) Uani 1 1 d . . . . .
O1 O 0.53051(17) 0.19956(16) 0.37390(4) 0.0508(4) Uani 1 1 d . . . . .
O2 O 0.85002(19) 0.3585(2) 0.36516(6) 0.0734(5) Uani 1 1 d . . . . .
O3 O 0.7294(2) 0.57331(19) 0.32942(7) 0.0798(6) Uani 1 1 d . . . . .
O4 O 0.6051(2) 0.4797(2) 0.39154(6) 0.0695(5) Uani 1 1 d . . . . .
O5 O 0.0412(4) -0.3482(3) 0.45807(9) 0.1391(12) Uani 1 1 d . . . . .
O6 O 0.0858(2) -0.2042(2) 0.51136(6) 0.0826(6) Uani 1 1 d . . . . .
N1 N 0.47198(19) 0.23530(19) 0.33195(5) 0.0479(4) Uani 1 1 d . . . . .
C1 C 0.5728(3) 0.0527(2) 0.37823(8) 0.0560(5) Uani 1 1 d . . . . .
H1 H 0.5803 0.0103 0.3502 0.067 Uiso 1 1 calc R . . . .
C2 C 0.7315(3) 0.0480(3) 0.39956(9) 0.0726(7) Uani 1 1 d . . . . .
H2A H 0.8065 0.0932 0.3819 0.109 Uiso 1 1 calc GR . . . .
H2B H 0.7614 -0.0478 0.4040 0.109 Uiso 1 1 calc GR . . . .
H2C H 0.7266 0.0957 0.4261 0.109 Uiso 1 1 calc GR . . . .
C3 C 0.3048(2) 0.2822(3) 0.33645(8) 0.0582(6) Uani 1 1 d . . . . .
C4 C 0.2432(3) 0.3193(4) 0.29248(10) 0.0827(9) Uani 1 1 d . . . . .
H4A H 0.2984 0.3991 0.2818 0.124 Uiso 1 1 calc GR . . . .
H4B H 0.1347 0.3410 0.2941 0.124 Uiso 1 1 calc GR . . . .
H4C H 0.2579 0.2410 0.2739 0.124 Uiso 1 1 calc GR . . . .
C5 C 0.2800(3) 0.4037(4) 0.36601(12) 0.0908(10) Uani 1 1 d . . . . .
H5A H 0.3199 0.3803 0.3934 0.136 Uiso 1 1 calc GR . . . .
H5B H 0.1711 0.4235 0.3680 0.136 Uiso 1 1 calc GR . . . .
H5C H 0.3332 0.4848 0.3555 0.136 Uiso 1 1 calc GR . . . .
C6 C 0.2113(3) 0.1567(3) 0.35121(10) 0.0742(8) Uani 1 1 d . . . . .
H6A H 0.2339 0.0773 0.3337 0.111 Uiso 1 1 calc GR . . . .
H6B H 0.1027 0.1781 0.3494 0.111 Uiso 1 1 calc GR . . . .
H6C H 0.2382 0.1354 0.3799 0.111 Uiso 1 1 calc GR . . . .
C7 C 0.5808(2) 0.3411(2) 0.31433(7) 0.0489(5) Uani 1 1 d . . . . .
H7 H 0.5151 0.4149 0.3023 0.059 Uiso 1 1 calc R . . . .
C8 C 0.6749(3) 0.2787(3) 0.27605(7) 0.0563(5) Uani 1 1 d . . . . .
C9 C 0.7744(3) 0.1539(3) 0.28841(9) 0.0706(7) Uani 1 1 d . . . . .
H9A H 0.8425 0.1800 0.3111 0.106 Uiso 1 1 calc GR . . . .
H9B H 0.8348 0.1246 0.2647 0.106 Uiso 1 1 calc GR . . . .
H9C H 0.7090 0.0782 0.2973 0.106 Uiso 1 1 calc GR . . . .
C10 C 0.7800(4) 0.3910(3) 0.25665(10) 0.0825(9) Uani 1 1 d . . . . .
H10A H 0.7199 0.4734 0.2506 0.124 Uiso 1 1 calc GR . . . .
H10B H 0.8242 0.3557 0.2311 0.124 Uiso 1 1 calc GR . . . .
H10C H 0.8615 0.4141 0.2761 0.124 Uiso 1 1 calc GR . . . .
C11 C 0.5607(4) 0.2313(4) 0.24195(9) 0.0854(9) Uani 1 1 d . . . . .
H11A H 0.4922 0.1618 0.2533 0.128 Uiso 1 1 calc GR . . . .
H11B H 0.6169 0.1920 0.2188 0.128 Uiso 1 1 calc GR . . . .
H11C H 0.5013 0.3104 0.2324 0.128 Uiso 1 1 calc GR . . . .
C12 C 0.6270(5) 0.4321(4) 0.43460(10) 0.0974(11) Uani 1 1 d . . . . .
H12A H 0.7158 0.3699 0.4362 0.117 Uiso 1 1 calc R . . . .
H12B H 0.5362 0.3806 0.4438 0.117 Uiso 1 1 calc R . . . .
C13 C 0.6520(6) 0.5532(5) 0.46202(12) 0.1314(17) Uani 1 1 d . . . . .
H13A H 0.7393 0.6061 0.4521 0.197 Uiso 1 1 calc GR . . . .
H13B H 0.6720 0.5217 0.4902 0.197 Uiso 1 1 calc GR . . . .
H13C H 0.5612 0.6115 0.4617 0.197 Uiso 1 1 calc GR . . . .
C14 C 0.8438(15) 0.6669(11) 0.3519(4) 0.109(3) Uani 0.63(2) 1 d . . P A -1
H14A H 0.7943 0.7102 0.3760 0.131 Uiso 0.63(2) 1 calc R . P A -1
H14B H 0.9306 0.6115 0.3620 0.131 Uiso 0.63(2) 1 calc R . P A -1
C15 C 0.8978(15) 0.7716(12) 0.3244(3) 0.109(3) Uani 0.63(2) 1 d . . P A -1
H15A H 0.9748 0.8273 0.3385 0.163 Uiso 0.63(2) 1 calc GR . P A -1
H15B H 0.8128 0.8303 0.3159 0.163 Uiso 0.63(2) 1 calc GR . P A -1
H15C H 0.9426 0.7285 0.3000 0.163 Uiso 0.63(2) 1 calc GR . P A -1
C16 C 0.792(2) 0.7013(18) 0.3446(8) 0.111(5) Uani 0.37(2) 1 d . . P A 1
H16A H 0.7958 0.7026 0.3751 0.133 Uiso 0.37(2) 1 calc R . P A 1
H16B H 0.7317 0.7808 0.3347 0.133 Uiso 0.37(2) 1 calc R . P A 1
C17 C 0.9463(17) 0.702(2) 0.3268(5) 0.111(5) Uani 0.37(2) 1 d . . P A 1
H17A H 0.9445 0.7506 0.3003 0.166 Uiso 0.37(2) 1 calc GR . P A 1
H17B H 0.9809 0.6077 0.3227 0.166 Uiso 0.37(2) 1 calc GR . P A 1
H17C H 1.0160 0.7495 0.3458 0.166 Uiso 0.37(2) 1 calc GR . P A 1
C18 C 0.4553(3) -0.0269(3) 0.40384(7) 0.0562(5) Uani 1 1 d . . . . .
C19 C 0.3920(3) -0.1510(3) 0.38898(9) 0.0709(7) Uani 1 1 d . . . . .
H19 H 0.4245 -0.1866 0.3632 0.085 Uiso 1 1 calc R . . . .
C20 C 0.2816(4) -0.2225(3) 0.41173(10) 0.0777(8) Uani 1 1 d . . . . .
H20 H 0.2395 -0.3049 0.4010 0.093 Uiso 1 1 calc R . . . .
C21 C 0.2331(3) -0.1728(3) 0.45040(8) 0.0636(6) Uani 1 1 d . . . . .
C22 C 0.2994(3) -0.0512(3) 0.46627(8) 0.0652(6) Uani 1 1 d . . . . .
H22 H 0.2699 -0.0179 0.4926 0.078 Uiso 1 1 calc R . . . .
C23 C 0.4092(3) 0.0205(3) 0.44325(8) 0.0645(6) Uani 1 1 d . . . . .
H23 H 0.4529 0.1019 0.4543 0.077 Uiso 1 1 calc R . . . .
C24 C 0.1110(4) -0.2515(3) 0.47309(10) 0.0769(8) Uani 1 1 d . . . . .
C25 C -0.0317(4) -0.2746(4) 0.53615(11) 0.0930(10) Uani 1 1 d . . . . .
H25A H -0.1326 -0.2521 0.5252 0.140 Uiso 1 1 calc GR . . . .
H25B H -0.0244 -0.2442 0.5649 0.140 Uiso 1 1 calc GR . . . .
H25C H -0.0159 -0.3742 0.5348 0.140 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4621(18) . ?
P1 O3 1.581(2) . ?
P1 O4 1.5702(19) . ?
P1 C7 1.844(2) . ?
O1 N1 1.463(2) . ?
O1 C1 1.454(3) . ?
O3 C14 1.508(9) . ?
O3 C16 1.417(17) . ?
O4 C12 1.452(4) . ?
O5 C24 1.199(4) . ?
O6 C24 1.315(4) . ?
O6 C25 1.451(3) . ?
N1 C3 1.517(3) . ?
N1 C7 1.489(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.524(3) . ?
C1 C18 1.507(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.533(4) . ?
C3 C5 1.508(4) . ?
C3 C6 1.518(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9800 . ?
C7 C8 1.581(3) . ?
C8 C9 1.518(4) . ?
C8 C10 1.534(4) . ?
C8 C11 1.528(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.462(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.407(16) . ?
C14 C16 0.600(19) . ?
C14 C17 1.239(13) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C16 1.303(17) . ?
C15 C17 0.785(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.45(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.385(3) . ?
C18 C23 1.391(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(4) . ?
C21 C22 1.386(4) . ?
C21 C24 1.483(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(4) . ?
C23 H23 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 114.54(12) . . ?
O2 P1 O4 114.63(11) . . ?
O2 P1 C7 116.97(11) . . ?
O3 P1 C7 98.57(11) . . ?
O4 P1 O3 100.37(11) . . ?
O4 P1 C7 109.47(10) . . ?
C1 O1 N1 113.32(16) . . ?
C14 O3 P1 111.7(5) . . ?
C16 O3 P1 129.2(10) . . ?
C16 O3 C14 23.4(8) . . ?
C12 O4 P1 124.2(2) . . ?
C24 O6 C25 117.5(3) . . ?
O1 N1 C3 107.87(16) . . ?
O1 N1 C7 106.55(15) . . ?
C7 N1 C3 115.91(17) . . ?
O1 C1 H1 109.2 . . ?
O1 C1 C2 107.1(2) . . ?
O1 C1 C18 111.54(19) . . ?
C2 C1 H1 109.2 . . ?
C18 C1 H1 109.2 . . ?
C18 C1 C2 110.5(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 107.9(2) . . ?
N1 C3 C6 107.6(2) . . ?
C5 C3 N1 115.0(2) . . ?
C5 C3 C4 109.9(3) . . ?
C5 C3 C6 109.7(2) . . ?
C6 C3 C4 106.3(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
P1 C7 H7 105.6 . . ?
N1 C7 P1 115.18(15) . . ?
N1 C7 H7 105.6 . . ?
N1 C7 C8 111.14(18) . . ?
C8 C7 P1 112.85(15) . . ?
C8 C7 H7 105.6 . . ?
C9 C8 C7 112.8(2) . . ?
C9 C8 C10 108.5(2) . . ?
C9 C8 C11 108.2(2) . . ?
C10 C8 C7 110.6(2) . . ?
C11 C8 C7 109.0(2) . . ?
C11 C8 C10 107.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 H12A 109.8 . . ?
O4 C12 H12B 109.8 . . ?
O4 C12 C13 109.4(3) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.6 . . ?
O3 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 O3 110.1(9) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C16 C14 O3 70(2) . . ?
C16 C14 H14A 75.2 . . ?
C16 C14 H14B 176.5 . . ?
C16 C14 C15 68(3) . . ?
C16 C14 C17 98(3) . . ?
C17 C14 O3 109.0(10) . . ?
C17 C14 H14A 135.1 . . ?
C17 C14 H14B 79.1 . . ?
C17 C14 C15 33.8(8) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 C14 25.2(8) . . ?
C16 C15 H15A 122.7 . . ?
C16 C15 H15B 84.4 . . ?
C16 C15 H15C 117.5 . . ?
C17 C15 C14 61.3(13) . . ?
C17 C15 H15A 93.0 . . ?
C17 C15 H15B 157.6 . . ?
C17 C15 H15C 60.2 . . ?
C17 C15 C16 83.9(15) . . ?
O3 C16 H16A 111.2 . . ?
O3 C16 H16B 111.2 . . ?
O3 C16 C17 102.9(13) . . ?
C14 C16 O3 87(2) . . ?
C14 C16 C15 87(3) . . ?
C14 C16 H16A 66.3 . . ?
C14 C16 H16B 161.5 . . ?
C14 C16 C17 58(2) . . ?
C15 C16 O3 122.8(15) . . ?
C15 C16 H16A 117.6 . . ?
C15 C16 H16B 79.3 . . ?
C15 C16 C17 32.6(7) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
C14 C17 C16 24.3(10) . . ?
C14 C17 H17A 133.3 . . ?
C14 C17 H17B 93.1 . . ?
C14 C17 H17C 99.9 . . ?
C15 C17 C14 84.9(17) . . ?
C15 C17 C16 63.5(13) . . ?
C15 C17 H17A 60.3 . . ?
C15 C17 H17B 160.5 . . ?
C15 C17 H17C 90.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C1 120.8(2) . . ?
C19 C18 C23 118.1(2) . . ?
C23 C18 C1 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 C24 118.4(2) . . ?
C22 C21 C24 122.7(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
O5 C24 O6 123.1(3) . . ?
O5 C24 C21 123.5(3) . . ?
O6 C24 C21 113.3(2) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/ethyl aceate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jp293rssr1
_database_code_depnum_ccdc_archive 'CCDC 1452314'
_audit_update_record             
;
2016-02-09 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'Diethyl (1-(tert-butyl(1-(4-fluorophenyl)ethoxy)amino)-2,2-dimethylpropyl)phosphonate'
_chemical_formula_moiety         'C21 H37 F N O4 P'
_chemical_formula_sum            'C21 H37 F N O4 P'
_chemical_formula_weight         417.48
_chemical_melting_point          56
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0712(3)
_cell_length_b                   10.2972(3)
_cell_length_c                   13.5576(3)
_cell_angle_alpha                75.983(2)
_cell_angle_beta                 80.691(2)
_cell_angle_gamma                78.803(2)
_cell_volume                     1196.51(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6910
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.1570
_cell_measurement_theta_min      4.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.166
_diffrn_reflns_theta_min         3.385
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2264  -77.0000    0.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega   34.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2264 -125.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000  150.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega   43.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917 -111.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega   62.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   31.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   51.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2264 -125.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   22.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  -94.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega   99.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   55.0000 -128.1384 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  101.00  131.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega  101.00  174.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917  111.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
 13 omega   91.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -113.9069 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   97.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega  110.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
 16 omega  112.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   66.0000   13.9638 44

#__ type_ start__ end____ width___ exp.time_
 17 omega  107.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000   61.1465 49

#__ type_ start__ end____ width___ exp.time_
 18 omega   96.00  170.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 19 omega   64.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   65.00   92.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000   90.0000 113

#__ type_ start__ end____ width___ exp.time_
 23 omega   64.00  155.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
 24 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 25 omega   66.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 26 omega   65.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   61.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   65.00  137.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
 28 omega   64.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -30.0000 113

#__ type_ start__ end____ width___ exp.time_
 29 omega   64.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   64.00  146.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
 31 omega   64.00  143.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 32 omega   64.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.3917   77.0000 -120.0000 105

#__ type_ start__ end____ width___ exp.time_
 33 omega   52.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   55.0000 -128.1384 30

#__ type_ start__ end____ width___ exp.time_
 34 omega   16.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   82.0000 -148.3664 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   21.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -113.9069 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   80.0000  -94.7238 25

#__ type_ start__ end____ width___ exp.time_
 37 omega   20.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   79.0000  -59.0022 27

#__ type_ start__ end____ width___ exp.time_
 38 omega   20.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  -25.4904 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   25.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   66.0000   13.9638 42

#__ type_ start__ end____ width___ exp.time_
 40 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  101.5362 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   21.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000   61.1465 30

#__ type_ start__ end____ width___ exp.time_
 42 omega   16.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   81.0000   86.3098 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   81.0000  135.5495 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   80.0000  177.4677 25

#__ type_ start__ end____ width___ exp.time_
 45 omega  -26.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.2264  123.0000  127.3260 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   94.0000   -8.6886 25

#__ type_ start__ end____ width___ exp.time_
 47 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   90.0000  -99.5638 25

#__ type_ start__ end____ width___ exp.time_
 48 omega  -16.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000  109.0000 -118.0507 25

#__ type_ start__ end____ width___ exp.time_
 49 omega  -93.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2264  125.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
 50 omega -127.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2264  -19.0000  -30.0000 129

#__ type_ start__ end____ width___ exp.time_
 51 omega -116.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2264  -57.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 52 omega -123.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.2264  -38.0000 -150.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0062803000
_diffrn_orient_matrix_UB_12      0.0383546000
_diffrn_orient_matrix_UB_13      0.1020735000
_diffrn_orient_matrix_UB_21      0.1366808000
_diffrn_orient_matrix_UB_22      -0.1134537000
_diffrn_orient_matrix_UB_23      0.0209388000
_diffrn_orient_matrix_UB_31      0.1081344000
_diffrn_orient_matrix_UB_32      0.1003750000
_diffrn_orient_matrix_UB_33      -0.0553307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3657
_reflns_number_total             4402
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0838P)²+0.2475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P11 P 0.38949(6) 0.81334(6) 0.73191(4) 0.0686(2) Uani 1 1 d . . . . .
F1 F 0.0701(2) 0.7521(2) 0.26510(11) 0.1172(6) Uani 1 1 d . . . . .
O1 O 0.22145(14) 0.62957(14) 0.71071(9) 0.0597(3) Uani 1 1 d . . . . .
O2 O 0.2855(2) 0.9251(2) 0.68028(16) 0.0992(6) Uani 1 1 d . . . . .
O3 O 0.49782(18) 0.73113(18) 0.65824(11) 0.0781(4) Uani 1 1 d . . . . .
O4 O 0.5109(2) 0.85369(19) 0.78640(14) 0.0901(5) Uani 1 1 d . . . . .
N1 N 0.23693(18) 0.59251(17) 0.81982(11) 0.0593(4) Uani 1 1 d . . . . .
C1 C 0.0686(2) 0.6876(2) 0.68884(15) 0.0625(5) Uani 1 1 d . . . . .
H1 H 0.0435 0.7775 0.7054 0.075 Uiso 1 1 calc R . . . .
C2 C 0.0730(2) 0.7049(2) 0.57465(15) 0.0619(5) Uani 1 1 d . . . . .
C3 C -0.0066(3) 0.8189(3) 0.51879(18) 0.0787(6) Uani 1 1 d . . . . .
H3 H -0.0590 0.8868 0.5516 0.094 Uiso 1 1 calc R . . . .
C4 C -0.0106(3) 0.8351(3) 0.4147(2) 0.0916(8) Uani 1 1 d . . . . .
H4 H -0.0669 0.9115 0.3779 0.110 Uiso 1 1 calc R . . . .
C5 C 0.0699(3) 0.7363(3) 0.36792(17) 0.0834(7) Uani 1 1 d . . . . .
C6 C 0.1505(3) 0.6228(3) 0.41915(19) 0.0876(7) Uani 1 1 d . . . . .
H6 H 0.2049 0.5569 0.3851 0.105 Uiso 1 1 calc R . . . .
C7 C 0.1502(3) 0.6068(3) 0.52329(18) 0.0817(7) Uani 1 1 d . . . . .
H7 H 0.2034 0.5280 0.5597 0.098 Uiso 1 1 calc R . . . .
C8 C -0.0506(3) 0.6030(3) 0.74738(18) 0.0794(6) Uani 1 1 d . . . . .
H8A H -0.0319 0.5172 0.7277 0.119 Uiso 1 1 calc GR . . . .
H8B H -0.1491 0.6500 0.7319 0.119 Uiso 1 1 calc GR . . . .
H8C H -0.0459 0.5882 0.8196 0.119 Uiso 1 1 calc GR . . . .
C9 C 0.3297(3) 0.4517(2) 0.83703(18) 0.0731(6) Uani 1 1 d . . . . .
C10 C 0.4891(3) 0.4440(3) 0.7803(3) 0.0976(8) Uani 1 1 d . . . . .
H10A H 0.4839 0.4723 0.7079 0.146 Uiso 1 1 calc GR . . . .
H10B H 0.5413 0.3523 0.7959 0.146 Uiso 1 1 calc GR . . . .
H10C H 0.5428 0.5024 0.8012 0.146 Uiso 1 1 calc GR . . . .
C11 C 0.3371(4) 0.4005(3) 0.9525(2) 0.1018(9) Uani 1 1 d . . . . .
H11A H 0.3879 0.4584 0.9765 0.153 Uiso 1 1 calc GR . . . .
H11B H 0.3919 0.3096 0.9655 0.153 Uiso 1 1 calc GR . . . .
H11C H 0.2363 0.4014 0.9877 0.153 Uiso 1 1 calc GR . . . .
C12 C 0.2451(3) 0.3582(3) 0.8037(2) 0.0935(8) Uani 1 1 d . . . . .
H12A H 0.1443 0.3631 0.8391 0.140 Uiso 1 1 calc GR . . . .
H12B H 0.2973 0.2666 0.8198 0.140 Uiso 1 1 calc GR . . . .
H12C H 0.2405 0.3860 0.7312 0.140 Uiso 1 1 calc GR . . . .
C13 C 0.3057(2) 0.6990(2) 0.84405(14) 0.0602(5) Uani 1 1 d . . . . .
H13 H 0.3904 0.6502 0.8819 0.072 Uiso 1 1 calc R . . . .
C14 C 0.1942(3) 0.7782(3) 0.92052(17) 0.0774(6) Uani 1 1 d . . . . .
C15 C 0.1536(4) 0.6746(4) 1.0192(2) 0.1142(11) Uani 1 1 d . . . . .
H15A H 0.1044 0.6089 1.0034 0.171 Uiso 1 1 calc GR . . . .
H15B H 0.0868 0.7206 1.0670 0.171 Uiso 1 1 calc GR . . . .
H15C H 0.2443 0.6296 1.0489 0.171 Uiso 1 1 calc GR . . . .
C16 C 0.2708(4) 0.8792(4) 0.9514(3) 0.1172(12) Uani 1 1 d . . . . .
H16A H 0.3659 0.8341 0.9749 0.176 Uiso 1 1 calc GR . . . .
H16B H 0.2068 0.9154 1.0054 0.176 Uiso 1 1 calc GR . . . .
H16C H 0.2881 0.9517 0.8934 0.176 Uiso 1 1 calc GR . . . .
C17 C 0.0473(3) 0.8490(4) 0.8789(2) 0.1035(10) Uani 1 1 d . . . . .
H17A H 0.0683 0.9169 0.8184 0.155 Uiso 1 1 calc GR . . . .
H17B H -0.0175 0.8911 0.9296 0.155 Uiso 1 1 calc GR . . . .
H17C H -0.0019 0.7839 0.8623 0.155 Uiso 1 1 calc GR . . . .
C18 C 0.4754(4) 0.7401(5) 0.5541(2) 0.1330(15) Uani 1 1 d . . . . .
H18A H 0.4344 0.6610 0.5512 0.160 Uiso 1 1 calc R . . . .
H18B H 0.4007 0.8194 0.5333 0.160 Uiso 1 1 calc R . . . .
C19 C 0.6026(5) 0.7482(6) 0.4862(3) 0.1603(19) Uani 1 1 d . . . . .
H19A H 0.6299 0.8365 0.4755 0.240 Uiso 1 1 calc GR . . . .
H19B H 0.5842 0.7334 0.4223 0.240 Uiso 1 1 calc GR . . . .
H19C H 0.6836 0.6805 0.5128 0.240 Uiso 1 1 calc GR . . . .
C20 C 0.5936(6) 0.9605(5) 0.7343(4) 0.1504(17) Uani 1 1 d . . . . .
H20A H 0.6730 0.9272 0.6851 0.180 Uiso 1 1 calc R . . . .
H20B H 0.5261 1.0341 0.6969 0.180 Uiso 1 1 calc R . . . .
C21 C 0.6578(6) 1.0096(5) 0.8012(5) 0.185(2) Uani 1 1 d . . . . .
H21A H 0.5802 1.0393 0.8518 0.278 Uiso 1 1 calc GR . . . .
H21B H 0.7068 1.0846 0.7637 0.278 Uiso 1 1 calc GR . . . .
H21C H 0.7309 0.9390 0.8344 0.278 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P11 O2 1.4515(19) . ?
P11 O3 1.5649(17) . ?
P11 O4 1.5880(18) . ?
P11 C13 1.839(2) . ?
F1 C5 1.364(3) . ?
O1 N1 1.4583(18) . ?
O1 C1 1.447(2) . ?
O3 C18 1.437(3) . ?
O4 C20 1.430(4) . ?
N1 C9 1.514(3) . ?
N1 C13 1.485(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.510(3) . ?
C1 C8 1.521(3) . ?
C2 C3 1.376(3) . ?
C2 C7 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(4) . ?
C5 C6 1.350(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.521(4) . ?
C9 C11 1.534(3) . ?
C9 C12 1.527(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.585(3) . ?
C14 C15 1.538(4) . ?
C14 C16 1.526(4) . ?
C14 C17 1.514(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.357(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.387(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P11 O3 113.94(11) . . ?
O2 P11 O4 115.99(12) . . ?
O2 P11 C13 116.20(11) . . ?
O3 P11 O4 99.76(10) . . ?
O3 P11 C13 111.00(9) . . ?
O4 P11 C13 97.76(9) . . ?
C1 O1 N1 113.45(13) . . ?
C18 O3 P11 124.0(2) . . ?
C20 O4 P11 120.4(2) . . ?
O1 N1 C9 105.24(14) . . ?
O1 N1 C13 107.68(14) . . ?
C13 N1 C9 115.58(15) . . ?
O1 C1 H1 108.6 . . ?
O1 C1 C2 105.26(15) . . ?
O1 C1 C8 114.24(17) . . ?
C2 C1 H1 108.6 . . ?
C2 C1 C8 111.30(17) . . ?
C8 C1 H1 108.6 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 C7 117.6(2) . . ?
C7 C2 C1 122.27(19) . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 F1 119.0(3) . . ?
C6 C5 F1 118.4(3) . . ?
C6 C5 C4 122.6(2) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.4(3) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C6 121.6(2) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 114.3(2) . . ?
N1 C9 C11 108.0(2) . . ?
N1 C9 C12 108.09(18) . . ?
C10 C9 C11 109.7(2) . . ?
C10 C9 C12 109.3(2) . . ?
C12 C9 C11 107.2(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P11 C13 H13 105.5 . . ?
N1 C13 P11 114.83(12) . . ?
N1 C13 H13 105.5 . . ?
N1 C13 C14 111.92(17) . . ?
C14 C13 P11 112.71(15) . . ?
C14 C13 H13 105.5 . . ?
C15 C14 C13 108.1(2) . . ?
C16 C14 C13 111.3(2) . . ?
C16 C14 C15 106.6(2) . . ?
C17 C14 C13 113.14(17) . . ?
C17 C14 C15 107.3(2) . . ?
C17 C14 C16 110.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 108.7 . . ?
O3 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 O3 114.4(3) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.2 . . ?
O4 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 O4 112.2(4) . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether- ethyl acetate'
