# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2114683'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-02-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
hossein.rouh@ttu.edu
daniel.unruh@ttu.edu
guigen.li@ttu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H40 N3 O4 P'
_chemical_formula_sum            'C30 H40 N3 O4 P'
_chemical_formula_weight         537.62
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C120  H160  N12  O16  P4  '
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.46724(4)
_cell_length_b                   21.50060(15)
_cell_length_c                   23.19943(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2727.07(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26149
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.4720
_cell_measurement_theta_min      2.7520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 14 2 0.0286
0 -14 -3 0.0356
3 -7 5 0.0964
3 7 7 0.0846
-3 3 0 0.1189
3 -3 -2 0.1106
0 -1 15 0.0278
1 -3 14 0.0503
2 0 -14 0.0617
0 -7 -13 0.0308
1 5 14 0.0452
0 6 13 0.0272
0 11 -10 0.0276
0 4 -14 0.0202
2 -9 -9 0.0633
0 -7 -13 0.0278
0 -14 2 0.0327
0 -8 12 0.0268

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Slow evaporation from methanol'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.057
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0153 13.8214 2.0761 -0.2285 -0.9554 -0.1873
-0.4415 -13.5583 -3.0305 0.2326 0.9716 0.0435
2.7646 -7.4982 4.8745 0.0731 0.3105 0.9478
2.6245 6.9843 6.7798 -0.1641 -0.6812 0.7135
-3.4701 2.9369 -0.0446 0.3939 -0.1380 -0.9087
3.4604 -2.7317 -1.6002 -0.4858 0.1705 0.8573
-0.3750 -1.4664 14.8902 0.8848 -0.3132 0.3449
0.9646 -2.5196 14.2347 0.6948 -0.2465 0.6757
1.5140 0.3514 -13.6142 -0.9428 0.3332 -0.0091
0.0032 -6.5970 -13.2714 -0.5484 0.7975 -0.2513
0.8675 4.9408 13.5951 0.4891 -0.7119 0.5040
0.1040 6.4198 13.3648 0.5434 -0.7902 0.2834
-0.0484 10.6742 -9.6947 -0.7769 -0.4231 -0.4662
-0.3092 4.4845 -14.1988 -0.8300 0.1081 -0.5472
1.6485 -9.4476 -8.6006 -0.4500 0.8284 0.3336
-0.4055 -7.2111 -12.7786 -0.4516 0.8298 -0.3278
-0.2780 -13.7273 2.4294 0.5072 0.8283 0.2379
-0.2149 -7.8129 12.4418 0.8890 0.1648 0.4273

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_min         2.802
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  25.00   0.50    0.82    --  -48.34  38.00  84.00  132
  2  ω    -49.00 -14.00   0.50    3.29    --  -86.25  45.00 -60.00   70
  3  ω    -24.00  27.00   0.50    0.82    --  -48.34  19.00-120.00  102
  4  ω    -81.00 -13.00   0.50    3.29    --  -86.25 107.00 -61.00  136
  5  ω   -121.00 -36.00   0.50    0.82    --  -48.34 -38.00 -71.00  170
  6  ω   -120.00 -73.00   0.50    0.82    --  -48.34-125.00-150.00   94
  7  ω   -120.00 -26.00   0.50    0.82    --  -48.34 -77.00-180.00  188
  8  ω   -120.00 -73.00   0.50    0.82    --  -48.34-125.00   0.00   94
  9  ω   -120.00 -33.00   0.50    0.82    --  -48.34 -57.00-120.00  174
 10  ω     34.00 120.00   0.50    0.82    --   48.34  57.00  60.00  172
 11  ω    105.00 178.00   0.50    3.29    --  107.75 107.00 -61.00  146
 12  ω     95.00 178.00   0.50    3.29    --  107.75  38.00  84.00  166
 13  ω     95.00 178.00   0.50    3.29    --  107.75 125.00 -30.00  166
 14  ω     95.00 178.00   0.50    3.29    --  107.75  45.00-150.00  166
 15  ω     35.00 107.00   0.50    3.29    --  107.75 -77.00 -60.00  144
 16  ω     35.00 106.00   0.50    3.29    --  107.75 -90.00  95.00  142
 17  ω     35.00  73.00   0.50    3.29    --  107.75 -61.00 120.00   76
 18  ω     35.00  73.00   0.50    3.29    --  107.75 -61.00 150.00   76
 19  ω     35.00  73.00   0.50    3.29    --  107.75 -61.00  90.00   76
 20  ω     35.00 112.00   0.50    3.29    --  107.75-125.00  60.00  154
 21  ω     35.00  73.00   0.50    3.29    --  107.75 -61.00 -60.00   76
 22  ω     95.00 178.00   0.50    3.29    --  107.75  30.00 150.00  166
 23  ω   -159.00 -79.00   0.50    3.29    --  -86.25 -90.00  95.00  160
 24  ω   -159.00-107.00   0.50    3.29    --  -86.25 -77.00 -90.00  104
 25  ω   -159.00 -73.00   0.50    3.29    --  -86.25 -38.00 -71.00  172
 26  ω   -159.00 -63.00   0.50    3.29    --  -86.25 -77.00-150.00  192
 27  ω   -158.00 -73.00   0.50    3.29    --  -86.25 -45.00   0.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1351228000
_diffrn_orient_matrix_UB_12      -0.0247309000
_diffrn_orient_matrix_UB_13      0.0535864000
_diffrn_orient_matrix_UB_21      -0.0148563000
_diffrn_orient_matrix_UB_22      -0.0649621000
_diffrn_orient_matrix_UB_23      -0.0278055000
_diffrn_orient_matrix_UB_31      0.2467722000
_diffrn_orient_matrix_UB_32      -0.0174302000
_diffrn_orient_matrix_UB_33      0.0276607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4822
_reflns_number_total             5001
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1992 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5001
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.5086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0676
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C19(H19), C24(H24), C25(H25), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.54476(8) 0.48987(2) 0.54076(2) 0.01199(11) Uani 1 1 d . . . . .
O1 O 0.8024(2) 0.50557(6) 0.55415(5) 0.0159(3) Uani 1 1 d . . . . .
O2 O 0.0785(3) 0.63613(6) 0.67924(6) 0.0180(3) Uani 1 1 d . . . . .
O3 O 0.5772(3) 0.46140(6) 0.71613(6) 0.0199(3) Uani 1 1 d . . . . .
O4 O 0.2557(3) 0.47314(7) 0.77509(6) 0.0272(4) Uani 1 1 d . . . . .
N1 N 0.3713(3) 0.51432(8) 0.59509(7) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.227(5) 0.5169(11) 0.5875(10) 0.017 Uiso 1 1 d . U . . .
N2 N 0.4205(3) 0.51486(7) 0.48010(6) 0.0145(3) Uani 1 1 d . . . . .
N3 N 0.4884(3) 0.41498(7) 0.52726(6) 0.0135(3) Uani 1 1 d . . . . .
C1 C 0.4611(4) 0.55495(8) 0.64180(8) 0.0142(4) Uani 1 1 d . . . . .
H1A H 0.631683 0.544088 0.649939 0.017 Uiso 1 1 calc R U . . .
C2 C 0.3117(4) 0.54401(9) 0.69585(8) 0.0152(4) Uani 1 1 d . . . . .
C3 C 0.1274(4) 0.58303(9) 0.71005(8) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.2529(4) 0.65865(9) 0.64119(8) 0.0164(4) Uani 1 1 d . . . . .
C5 C 0.2189(4) 0.71921(9) 0.62173(9) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.082415 0.742051 0.632861 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3925(4) 0.74465(9) 0.58552(9) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.371235 0.784782 0.571420 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5990(4) 0.71079(9) 0.56993(9) 0.0212(4) Uani 1 1 d . . . . .
H7 H 0.717334 0.728635 0.546342 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6279(4) 0.65038(9) 0.58966(8) 0.0172(4) Uani 1 1 d . . . . .
H8 H 0.766659 0.627920 0.579414 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4503(4) 0.62283(8) 0.62485(8) 0.0150(4) Uani 1 1 d . . . . .
C10 C -0.0523(4) 0.57994(9) 0.75845(8) 0.0204(4) Uani 1 1 d . . . . .
H10A H -0.025815 0.614291 0.784139 0.031 Uiso 1 1 calc R U . . .
H10B H -0.031124 0.541597 0.779057 0.031 Uiso 1 1 calc R U . . .
H10C H -0.215454 0.581946 0.743268 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3697(4) 0.48994(9) 0.73301(8) 0.0167(4) Uani 1 1 d . . . . .
C12 C 0.6849(4) 0.41832(10) 0.75776(9) 0.0245(5) Uani 1 1 d . . . . .
H12A H 0.630973 0.429905 0.796117 0.029 Uiso 1 1 calc R U . . .
H12B H 0.861403 0.422676 0.756600 0.029 Uiso 1 1 calc R U . . .
C13 C 0.6204(4) 0.35105(9) 0.74744(8) 0.0192(4) Uani 1 1 d . . . . .
C14 C 0.7781(4) 0.31397(10) 0.71516(9) 0.0234(4) Uani 1 1 d . . . . .
H14 H 0.917186 0.331498 0.698777 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7301(4) 0.25128(10) 0.70716(9) 0.0265(5) Uani 1 1 d . . . . .
H15 H 0.836770 0.227034 0.685466 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5246(5) 0.22477(10) 0.73132(9) 0.0267(5) Uani 1 1 d . . . . .
H16 H 0.492580 0.182685 0.725935 0.032 Uiso 1 1 calc R U . . .
C17 C 0.3663(4) 0.26087(10) 0.76354(10) 0.0263(5) Uani 1 1 d . . . . .
H17 H 0.227466 0.243061 0.779807 0.032 Uiso 1 1 calc R U . . .
C18 C 0.4143(4) 0.32387(10) 0.77170(9) 0.0233(4) Uani 1 1 d . . . . .
H18 H 0.307485 0.347918 0.793546 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3231(4) 0.46409(8) 0.44462(8) 0.0141(4) Uani 1 1 d . . . . .
H19 H 0.449881 0.450661 0.417470 0.017 Uiso 1 1 calc R U . . .
C20 C 0.0873(4) 0.47632(9) 0.41138(8) 0.0166(4) Uani 1 1 d . . . . .
H20A H 0.110257 0.510638 0.384783 0.020 Uiso 1 1 calc R U . . .
H20B H -0.043317 0.487096 0.437845 0.020 Uiso 1 1 calc R U . . .
C21 C 0.0213(4) 0.41702(9) 0.37817(8) 0.0187(4) Uani 1 1 d . . . . .
H21A H -0.133535 0.423134 0.358576 0.022 Uiso 1 1 calc R U . . .
H21B H 0.145197 0.409240 0.349120 0.022 Uiso 1 1 calc R U . . .
C22 C 0.0018(4) 0.36028(9) 0.41779(8) 0.0195(4) Uani 1 1 d . . . . .
H22A H -0.022982 0.323366 0.394471 0.023 Uiso 1 1 calc R U . . .
H22B H -0.139862 0.365074 0.442575 0.023 Uiso 1 1 calc R U . . .
C23 C 0.2302(4) 0.35126(8) 0.45534(8) 0.0173(4) Uani 1 1 d . . . . .
H23A H 0.204771 0.317370 0.482283 0.021 Uiso 1 1 calc R U . . .
H23B H 0.370090 0.341238 0.431344 0.021 Uiso 1 1 calc R U . . .
C24 C 0.2764(4) 0.41169(8) 0.48798(8) 0.0141(4) Uani 1 1 d . . . . .
H24 H 0.128785 0.421945 0.509991 0.017 Uiso 1 1 calc R U . . .
C25 C 0.4527(4) 0.57944(8) 0.46038(8) 0.0176(4) Uani 1 1 d . . . . .
H25 H 0.577514 0.598193 0.485214 0.021 Uiso 1 1 calc R U . . .
C26 C 0.5488(4) 0.58323(10) 0.39882(9) 0.0222(4) Uani 1 1 d . . . . .
H26A H 0.695012 0.558745 0.395492 0.033 Uiso 1 1 calc R U . . .
H26B H 0.584836 0.625746 0.389466 0.033 Uiso 1 1 calc R U . . .
H26C H 0.427277 0.567567 0.372724 0.033 Uiso 1 1 calc R U . . .
C27 C 0.2200(4) 0.61764(9) 0.46832(10) 0.0260(5) Uani 1 1 d . . . . .
H27A H 0.096367 0.602882 0.442305 0.039 Uiso 1 1 calc R U . . .
H27B H 0.253969 0.660593 0.460365 0.039 Uiso 1 1 calc R U . . .
H27C H 0.163162 0.613474 0.507282 0.039 Uiso 1 1 calc R U . . .
C28 C 0.5167(4) 0.37101(8) 0.57594(8) 0.0157(4) Uani 1 1 d . . . . .
H28 H 0.628895 0.390516 0.603490 0.019 Uiso 1 1 calc R U . . .
C29 C 0.6382(4) 0.31081(9) 0.55588(9) 0.0192(4) Uani 1 1 d . . . . .
H29A H 0.527313 0.288232 0.531548 0.029 Uiso 1 1 calc R U . . .
H29B H 0.679413 0.285859 0.588789 0.029 Uiso 1 1 calc R U . . .
H29C H 0.784090 0.320504 0.534690 0.029 Uiso 1 1 calc R U . . .
C30 C 0.2794(4) 0.35768(10) 0.60848(8) 0.0204(4) Uani 1 1 d . . . . .
H30A H 0.207403 0.396172 0.620801 0.031 Uiso 1 1 calc R U . . .
H30B H 0.314049 0.332290 0.641526 0.031 Uiso 1 1 calc R U . . .
H30C H 0.167561 0.336189 0.583548 0.031 Uiso 1 1 calc R U . . .


_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 O1 1.4812(14) . ?
P1 N1 1.6625(16) . ?
P1 N2 1.6526(15) . ?
P1 N3 1.6690(15) . ?
O2 C3 1.373(2) . ?
O2 C4 1.387(2) . ?
O3 C11 1.348(3) . ?
O3 C12 1.462(2) . ?
O4 C11 1.213(2) . ?
N1 H1 0.81(3) . ?
N1 C1 1.476(2) . ?
N2 C19 1.467(2) . ?
N2 C25 1.472(2) . ?
N3 C24 1.476(2) . ?
N3 C28 1.481(2) . ?
C1 H1A 0.9800 . ?
C1 C2 1.515(3) . ?
C1 C9 1.513(2) . ?
C2 C3 1.352(3) . ?
C2 C11 1.482(3) . ?
C3 C10 1.493(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.508(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9800 . ?
C19 C20 1.525(3) . ?
C19 C24 1.532(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.533(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.531(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.535(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.525(2) . ?
C24 H24 0.9800 . ?
C25 H25 0.9800 . ?
C25 C26 1.524(3) . ?
C25 C27 1.525(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28 0.9800 . ?
C28 C29 1.527(3) . ?
C28 C30 1.528(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
O1 P1 N1 108.14(8) . . ?
O1 P1 N2 119.70(8) . . ?
O1 P1 N3 115.76(8) . . ?
N1 P1 N3 110.00(8) . . ?
N2 P1 N1 107.96(8) . . ?
N2 P1 N3 94.47(8) . . ?
C3 O2 C4 119.20(16) . . ?
C11 O3 C12 115.80(16) . . ?
P1 N1 H1 114.4(17) . . ?
C1 N1 P1 123.66(13) . . ?
C1 N1 H1 116.2(17) . . ?
C19 N2 P1 112.64(12) . . ?
C19 N2 C25 124.81(15) . . ?
C25 N2 P1 121.47(12) . . ?
C24 N3 P1 107.88(11) . . ?
C24 N3 C28 121.47(15) . . ?
C28 N3 P1 116.97(12) . . ?
N1 C1 H1A 108.5 . . ?
N1 C1 C2 109.68(15) . . ?
N1 C1 C9 111.55(15) . . ?
C2 C1 H1A 108.5 . . ?
C9 C1 H1A 108.5 . . ?
C9 C1 C2 110.13(15) . . ?
C3 C2 C1 120.48(17) . . ?
C3 C2 C11 120.32(17) . . ?
C11 C2 C1 119.20(17) . . ?
O2 C3 C10 107.48(16) . . ?
C2 C3 O2 122.28(17) . . ?
C2 C3 C10 130.23(18) . . ?
O2 C4 C5 116.21(18) . . ?
C9 C4 O2 121.22(17) . . ?
C9 C4 C5 122.56(18) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.58(19) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.80(19) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.65(19) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C1 119.85(17) . . ?
C4 C9 C8 117.83(17) . . ?
C8 C9 C1 122.20(18) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C2 111.61(16) . . ?
O4 C11 O3 122.07(18) . . ?
O4 C11 C2 126.26(18) . . ?
O3 C12 H12A 108.7 . . ?
O3 C12 H12B 108.7 . . ?
O3 C12 C13 114.13(17) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C14 C13 C12 119.3(2) . . ?
C18 C13 C12 121.95(19) . . ?
C18 C13 C14 118.65(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.5(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
N2 C19 H19 108.9 . . ?
N2 C19 C20 117.53(15) . . ?
N2 C19 C24 103.86(14) . . ?
C20 C19 H19 108.9 . . ?
C20 C19 C24 108.52(15) . . ?
C24 C19 H19 108.9 . . ?
C19 C20 H20A 110.1 . . ?
C19 C20 H20B 110.1 . . ?
C19 C20 C21 108.05(15) . . ?
H20A C20 H20B 108.4 . . ?
C21 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 112.18(15) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C21 C22 C23 112.61(17) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C22 C23 H23A 110.1 . . ?
C22 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C24 C23 C22 107.98(15) . . ?
C24 C23 H23A 110.1 . . ?
C24 C23 H23B 110.1 . . ?
N3 C24 C19 103.82(15) . . ?
N3 C24 C23 118.50(15) . . ?
N3 C24 H24 108.3 . . ?
C19 C24 H24 108.3 . . ?
C23 C24 C19 109.17(15) . . ?
C23 C24 H24 108.3 . . ?
N2 C25 H25 106.8 . . ?
N2 C25 C26 112.49(15) . . ?
N2 C25 C27 111.75(16) . . ?
C26 C25 H25 106.8 . . ?
C26 C25 C27 111.85(17) . . ?
C27 C25 H25 106.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C28 H28 106.8 . . ?
N3 C28 C29 110.73(15) . . ?
N3 C28 C30 114.06(16) . . ?
C29 C28 H28 106.8 . . ?
C29 C28 C30 111.14(16) . . ?
C30 C28 H28 106.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.81(3) 2.46(3) 3.258(2) 169(2) 1_455 yes
C10 H10B O4 0.96 2.15 2.873(3) 130.8 . yes
C12 H12B O4 0.97 2.45 3.360(3) 155.9 1_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 N1 C1 C2 -153.17(14) . . . . ?
P1 N1 C1 C9 84.6(2) . . . . ?
P1 N2 C19 C20 143.31(14) . . . . ?
P1 N2 C19 C24 23.48(18) . . . . ?
P1 N2 C25 C26 126.96(16) . . . . ?
P1 N2 C25 C27 -106.25(17) . . . . ?
P1 N3 C24 C19 41.66(15) . . . . ?
P1 N3 C24 C23 162.88(14) . . . . ?
P1 N3 C28 C29 -139.52(14) . . . . ?
P1 N3 C28 C30 94.23(17) . . . . ?
O1 P1 N1 C1 10.63(17) . . . . ?
O1 P1 N2 C19 123.41(13) . . . . ?
O1 P1 N2 C25 -45.22(17) . . . . ?
O1 P1 N3 C24 -151.56(11) . . . . ?
O1 P1 N3 C28 67.22(15) . . . . ?
O2 C4 C5 C6 177.56(18) . . . . ?
O2 C4 C9 C1 8.5(3) . . . . ?
O2 C4 C9 C8 -175.41(17) . . . . ?
O3 C12 C13 C14 94.1(2) . . . . ?
O3 C12 C13 C18 -89.4(2) . . . . ?
N1 P1 N2 C19 -112.42(13) . . . . ?
N1 P1 N2 C25 78.95(16) . . . . ?
N1 P1 N3 C24 85.52(13) . . . . ?
N1 P1 N3 C28 -55.71(15) . . . . ?
N1 C1 C2 C3 -99.0(2) . . . . ?
N1 C1 C2 C11 80.9(2) . . . . ?
N1 C1 C9 C4 96.4(2) . . . . ?
N1 C1 C9 C8 -79.5(2) . . . . ?
N2 P1 N1 C1 -120.23(15) . . . . ?
N2 P1 N3 C24 -25.44(13) . . . . ?
N2 P1 N3 C28 -166.66(14) . . . . ?
N2 C19 C20 C21 -179.62(16) . . . . ?
N2 C19 C24 N3 -39.83(17) . . . . ?
N2 C19 C24 C23 -167.11(15) . . . . ?
N3 P1 N1 C1 137.93(15) . . . . ?
N3 P1 N2 C19 0.29(14) . . . . ?
N3 P1 N2 C25 -168.34(15) . . . . ?
C1 C2 C3 O2 -4.9(3) . . . . ?
C1 C2 C3 C10 176.00(19) . . . . ?
C1 C2 C11 O3 8.1(2) . . . . ?
C1 C2 C11 O4 -174.58(19) . . . . ?
C2 C1 C9 C4 -25.7(2) . . . . ?
C2 C1 C9 C8 158.44(17) . . . . ?
C3 O2 C4 C5 -165.43(17) . . . . ?
C3 O2 C4 C9 13.4(3) . . . . ?
C3 C2 C11 O3 -171.96(17) . . . . ?
C3 C2 C11 O4 5.3(3) . . . . ?
C4 O2 C3 C2 -15.4(3) . . . . ?
C4 O2 C3 C10 163.89(16) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C5 C4 C9 C1 -172.73(18) . . . . ?
C5 C4 C9 C8 3.3(3) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C1 173.07(18) . . . . ?
C7 C8 C9 C4 -2.9(3) . . . . ?
C9 C1 C2 C3 24.1(2) . . . . ?
C9 C1 C2 C11 -156.00(16) . . . . ?
C9 C4 C5 C6 -1.3(3) . . . . ?
C11 O3 C12 C13 97.5(2) . . . . ?
C11 C2 C3 O2 175.19(16) . . . . ?
C11 C2 C3 C10 -3.9(3) . . . . ?
C12 O3 C11 O4 -12.7(3) . . . . ?
C12 O3 C11 C2 164.72(16) . . . . ?
C12 C13 C14 C15 176.93(19) . . . . ?
C12 C13 C18 C17 -176.92(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C19 N2 C25 C26 -40.2(2) . . . . ?
C19 N2 C25 C27 86.6(2) . . . . ?
C19 C20 C21 C22 55.5(2) . . . . ?
C20 C19 C24 N3 -165.61(14) . . . . ?
C20 C19 C24 C23 67.11(19) . . . . ?
C20 C21 C22 C23 -52.8(2) . . . . ?
C21 C22 C23 C24 54.4(2) . . . . ?
C22 C23 C24 N3 -179.79(16) . . . . ?
C22 C23 C24 C19 -61.3(2) . . . . ?
C24 N3 C28 C29 84.8(2) . . . . ?
C24 N3 C28 C30 -41.4(2) . . . . ?
C24 C19 C20 C21 -62.27(19) . . . . ?
C25 N2 C19 C20 -48.5(2) . . . . ?
C25 N2 C19 C24 -168.34(16) . . . . ?
C28 N3 C24 C19 -179.22(15) . . . . ?
C28 N3 C24 C23 -58.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron MicroLoop'
_olex2_submission_original_sample_id Li21_03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1571
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.328
_oxdiff_exptl_absorpt_empirical_full_min 0.567
