# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_202012316
_database_code_depnum_ccdc_archive 'CCDC 2155267'
loop_
_audit_author_name
_audit_author_address
Liminyi
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2020-12-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H31 N3 O5'
_chemical_formula_sum            'C28 H31 N3 O5'
_chemical_formula_weight         489.56
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.5012(5)
_cell_length_b                   17.0320(7)
_cell_length_c                   18.9074(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2737.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6570
_cell_measurement_theta_min      5.1770
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10617
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.777
_diffrn_reflns_theta_min         3.493
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -26.00   1.00    2.00    --  -33.50 -77.00  90.00   76
  2  ω    -62.00   1.00   1.00    2.00    --  -33.50  77.00-180.00   63
  3  ω    -82.00 -32.00   1.00    2.00    --  -33.50 178.00 120.00   50
  4  ω     70.00 105.00   1.00    2.00    --   36.47 178.00  30.00   35
  5  ω     58.00 110.00   1.00    2.00    --   36.47 178.00-180.00   52
  6  ω     42.00  67.00   1.00    2.00    --   36.47 -99.00  90.00   25
  7  ω     32.00  58.00   1.00    2.00    --   36.47  57.00-150.00   26
  8  ω     74.00 101.00   1.00    2.00    --   36.47  57.00-150.00   27
  9  ω     12.00  38.00   1.00    2.00    --   36.47 -99.00  90.00   26
 10  ω     81.00 107.00   1.00    2.00    --   36.47 178.00 -60.00   26
 11  ω     42.00  68.00   1.00   13.00    --  108.00 -94.00  90.00   26
 12  ω    112.00 177.00   1.00   13.00    --  108.00 111.00 -60.00   65
 13  ω     38.00 110.00   1.00   13.00    --  108.00 -94.00   0.00   72
 14  ω     49.00 102.00   1.00   13.00    --  108.00 -61.00  60.00   53
 15  ω    122.00 178.00   1.00   13.00    --  108.00 111.00  60.00   56
 16  ω     50.00 132.00   1.00   13.00    --  108.00 -30.00 120.00   82
 17  ω     72.00 100.00   1.00   13.00    --  108.00 -94.00 150.00   28
 18  ω     63.00  89.00   1.00   13.00    --  108.00 -95.00 -85.00   26
 19  ω     51.00 128.00   1.00   13.00    --  108.00 -30.00 -30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1448656000
_diffrn_orient_matrix_UB_12      -0.0189623000
_diffrn_orient_matrix_UB_13      -0.0458578000
_diffrn_orient_matrix_UB_21      0.0860251000
_diffrn_orient_matrix_UB_22      0.0319446000
_diffrn_orient_matrix_UB_23      -0.0656952000
_diffrn_orient_matrix_UB_31      0.0666950000
_diffrn_orient_matrix_UB_32      -0.0824656000
_diffrn_orient_matrix_UB_33      -0.0148900000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3979
_reflns_number_total             5157
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.206
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.027
_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)+(0.0604P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1393
_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. Restrained distances
 C19A-C20A
 1.55 with sigma of 0.02
 H2A-N2
 0.87 with sigma of 0.02
 N3-H3A
 0.87 with sigma of 0.02
 C22-C23
 1.65 with sigma of 0.02
 C22A-C23A
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C19A(H19C,H19D), C22(H22A,H22B), C22A(H22C,H22D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C23(H23A,H23B,H23C), C23A(H23D,
 H23E,H23F), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.6033(6) 0.4838(2) 0.0584(2) 0.0718(10) Uani 1 1 d . . . . .
H1 H 0.5526 0.5041 0.0980 0.086 Uiso 1 1 calc R . . . .
C2 C 0.6763(7) 0.5338(3) 0.0108(2) 0.0876(14) Uani 1 1 d . . . . .
H2 H 0.6752 0.5877 0.0189 0.105 Uiso 1 1 calc R . . . .
C3 C 0.7506(7) 0.5042(3) -0.0483(2) 0.0908(14) Uani 1 1 d . . . . .
H3 H 0.7991 0.5381 -0.0802 0.109 Uiso 1 1 calc R . . . .
C4 C 0.7527(6) 0.4251(3) -0.0600(2) 0.0816(12) Uani 1 1 d . . . . .
H4 H 0.8030 0.4052 -0.0998 0.098 Uiso 1 1 calc R . . . .
C5 C 0.6805(5) 0.3746(2) -0.0130(2) 0.0708(10) Uani 1 1 d . . . . .
H5 H 0.6819 0.3208 -0.0215 0.085 Uiso 1 1 calc R . . . .
C6 C 0.6059(4) 0.4035(2) 0.04698(18) 0.0594(8) Uani 1 1 d . . . . .
C7 C 0.5281(4) 0.3500(2) 0.09713(19) 0.0580(8) Uani 1 1 d . . . . .
C8 C 0.5297(4) 0.34944(19) 0.17256(18) 0.0548(7) Uani 1 1 d . . . . .
C9 C 0.4330(4) 0.28831(19) 0.1894(2) 0.0620(8) Uani 1 1 d . . . . .
C10 C 0.6290(4) 0.39780(18) 0.22317(17) 0.0539(7) Uani 1 1 d . . . . .
C11 C 0.6803(5) 0.3483(2) 0.28383(19) 0.0631(9) Uani 1 1 d . . . . .
C12 C 0.7326(5) 0.3060(2) 0.32739(19) 0.0679(9) Uani 1 1 d . . . . .
C13 C 0.7923(6) 0.2524(3) 0.3800(2) 0.0771(11) Uani 1 1 d . . . . .
C14 C 0.9063(7) 0.2766(4) 0.4271(3) 0.0993(16) Uani 1 1 d . . . . .
H14 H 0.9463 0.3274 0.4246 0.119 Uiso 1 1 calc R . . . .
C15 C 0.9614(10) 0.2243(5) 0.4785(4) 0.132(3) Uani 1 1 d . . . . .
H15 H 1.0380 0.2401 0.5106 0.158 Uiso 1 1 calc R . . . .
C16 C 0.9031(10) 0.1510(6) 0.4813(5) 0.158(4) Uani 1 1 d . . . . .
H16 H 0.9389 0.1167 0.5160 0.190 Uiso 1 1 calc R . . . .
C17 C 0.7941(10) 0.1263(5) 0.4350(5) 0.150(3) Uani 1 1 d . . . . .
H17 H 0.7560 0.0752 0.4377 0.180 Uiso 1 1 calc R . . . .
C18 C 0.7381(8) 0.1765(3) 0.3833(4) 0.1125(19) Uani 1 1 d . . . . .
H18 H 0.6640 0.1589 0.3507 0.135 Uiso 1 1 calc R . . . .
C19 C 0.2672(12) 0.1965(7) 0.2562(7) 0.092(3) Uani 0.807(12) 1 d . . P A 1
H19A H 0.3037 0.1499 0.2317 0.110 Uiso 0.807(12) 1 calc R . P A 1
H19B H 0.1707 0.2139 0.2337 0.110 Uiso 0.807(12) 1 calc R . P A 1
C19A C 0.316(5) 0.186(3) 0.267(4) 0.092(3) Uani 0.193(12) 1 d D . P A 2
H19C H 0.3699 0.1610 0.3063 0.110 Uiso 0.193(12) 1 calc R . P A 2
H19D H 0.3173 0.1518 0.2267 0.110 Uiso 0.193(12) 1 calc R . P A 2
C20 C 0.2362(14) 0.1775(5) 0.3315(5) 0.133(4) Uani 0.807(12) 1 d . . P A 1
H20A H 0.2034 0.2241 0.3559 0.200 Uiso 0.807(12) 1 calc GR . P A 1
H20B H 0.3304 0.1574 0.3529 0.200 Uiso 0.807(12) 1 calc GR . P A 1
H20C H 0.1546 0.1386 0.3344 0.200 Uiso 0.807(12) 1 calc GR . P A 1
C20A C 0.146(5) 0.208(2) 0.288(2) 0.133(4) Uani 0.193(12) 1 d D . P A 2
H20D H 0.1468 0.2382 0.3310 0.200 Uiso 0.193(12) 1 calc GR . P A 2
H20E H 0.0856 0.1612 0.2949 0.200 Uiso 0.193(12) 1 calc GR . P A 2
H20F H 0.0991 0.2389 0.2510 0.200 Uiso 0.193(12) 1 calc GR . P A 2
C21 C 0.7866(4) 0.4249(2) 0.1894(2) 0.0627(9) Uani 1 1 d . . . . .
C22 C 1.0016(11) 0.3949(6) 0.1195(6) 0.087(2) Uani 0.571(7) 1 d D . P B 1
H22A H 0.9738 0.4379 0.0883 0.105 Uiso 0.571(7) 1 calc R . P B 1
H22B H 1.0834 0.4122 0.1516 0.105 Uiso 0.571(7) 1 calc R . P B 1
C22A C 1.0331(15) 0.3637(8) 0.1488(7) 0.087(2) Uani 0.429(7) 1 d D . P B 2
H22C H 1.0735 0.3108 0.1539 0.105 Uiso 0.429(7) 1 calc R . P B 2
H22D H 1.0866 0.3979 0.1821 0.105 Uiso 0.429(7) 1 calc R . P B 2
C23 C 1.0532(15) 0.3254(7) 0.0785(6) 0.123(3) Uani 0.571(7) 1 d D . P B 1
H23A H 1.0529 0.2800 0.1086 0.184 Uiso 0.571(7) 1 calc GR . P B 1
H23B H 1.1576 0.3341 0.0608 0.184 Uiso 0.571(7) 1 calc GR . P B 1
H23C H 0.9826 0.3171 0.0396 0.184 Uiso 0.571(7) 1 calc GR . P B 1
C23A C 1.052(2) 0.3928(11) 0.0742(8) 0.123(3) Uani 0.429(7) 1 d D . P B 2
H23D H 1.1578 0.4105 0.0672 0.184 Uiso 0.429(7) 1 calc GR . P B 2
H23E H 0.9804 0.4355 0.0661 0.184 Uiso 0.429(7) 1 calc GR . P B 2
H23F H 1.0291 0.3509 0.0418 0.184 Uiso 0.429(7) 1 calc GR . P B 2
C24 C 0.4260(5) 0.4716(2) 0.28937(19) 0.0611(8) Uani 1 1 d . . . . .
C25 C 0.2479(5) 0.5653(2) 0.3468(2) 0.0684(9) Uani 1 1 d . . . . .
C26 C 0.2526(8) 0.5281(3) 0.4187(3) 0.1028(16) Uani 1 1 d . . . . .
H26A H 0.2394 0.4724 0.4142 0.154 Uiso 1 1 calc GR . . . .
H26B H 0.1694 0.5491 0.4473 0.154 Uiso 1 1 calc GR . . . .
H26C H 0.3521 0.5390 0.4407 0.154 Uiso 1 1 calc GR . . . .
C27 C 0.1052(6) 0.5398(4) 0.3051(4) 0.1157(19) Uani 1 1 d . . . . .
H27A H 0.1086 0.5629 0.2588 0.174 Uiso 1 1 calc GR . . . .
H27B H 0.0115 0.5566 0.3290 0.174 Uiso 1 1 calc GR . . . .
H27C H 0.1047 0.4836 0.3009 0.174 Uiso 1 1 calc GR . . . .
C28 C 0.2591(8) 0.6542(3) 0.3527(4) 0.117(2) Uani 1 1 d . . . . .
H28A H 0.3497 0.6680 0.3803 0.176 Uiso 1 1 calc GR . . . .
H28B H 0.1661 0.6741 0.3752 0.176 Uiso 1 1 calc GR . . . .
H28C H 0.2685 0.6765 0.3062 0.176 Uiso 1 1 calc GR . . . .
N1 N 0.4409(4) 0.2935(2) 0.07079(18) 0.0754(9) Uani 1 1 d . . . . .
N2 N 0.3853(5) 0.2578(2) 0.2514(2) 0.0818(10) Uani 1 1 d D . . . .
H2A H 0.396(5) 0.289(2) 0.2861(16) 0.062(11) Uiso 1 1 d D . . . .
N3 N 0.5535(4) 0.47010(17) 0.24687(17) 0.0622(7) Uani 1 1 d D . . . .
H3A H 0.606(5) 0.5129(18) 0.241(2) 0.077(13) Uiso 1 1 d D . . . .
O1 O 0.3786(3) 0.25319(15) 0.13083(16) 0.0762(8) Uani 1 1 d . . . . .
O2 O 0.8327(4) 0.49092(18) 0.19390(19) 0.0882(9) Uani 1 1 d . . . . .
O3 O 0.8599(3) 0.36596(18) 0.15953(16) 0.0792(8) Uani 1 1 d . . . . .
O4 O 0.3553(4) 0.41389(14) 0.30881(19) 0.0884(10) Uani 1 1 d . . . . .
O5 O 0.3913(3) 0.54609(13) 0.30597(15) 0.0694(7) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 C2 1.386(6) . ?
C1 C6 1.383(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 C7 1.473(5) . ?
C7 C8 1.426(5) . ?
C7 N1 1.312(5) . ?
C8 C9 1.364(5) . ?
C8 C10 1.518(5) . ?
C9 N2 1.344(5) . ?
C9 O1 1.341(5) . ?
C10 C11 1.489(5) . ?
C10 C21 1.555(5) . ?
C10 N3 1.459(4) . ?
C11 C12 1.181(5) . ?
C12 C13 1.443(5) . ?
C13 C14 1.378(7) . ?
C13 C18 1.374(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.400(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.344(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.342(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(8) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.484(15) . ?
C19 N2 1.452(12) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C20A 1.54(3) . ?
C19A N2 1.38(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21 O2 1.195(5) . ?
C21 O3 1.309(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.480(14) . ?
C22 O3 1.506(10) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.503(17) . ?
C22A O3 1.486(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24 N3 1.350(5) . ?
C24 O4 1.209(4) . ?
C24 O5 1.340(4) . ?
C25 C26 1.501(6) . ?
C25 C27 1.511(7) . ?
C25 C28 1.520(6) . ?
C25 O5 1.479(5) . ?
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 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N1 O1 1.429(4) . ?
N2 H2A 0.85(2) . ?
N3 H3A 0.86(2) . ?

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
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 120.7(3) . . ?
C8 C7 C6 130.1(3) . . ?
N1 C7 C6 117.6(3) . . ?
N1 C7 C8 112.3(3) . . ?
C7 C8 C10 129.2(3) . . ?
C9 C8 C7 103.5(3) . . ?
C9 C8 C10 127.0(3) . . ?
N2 C9 C8 132.9(4) . . ?
O1 C9 C8 110.8(3) . . ?
O1 C9 N2 116.3(3) . . ?
C8 C10 C21 112.4(3) . . ?
C11 C10 C8 109.9(3) . . ?
C11 C10 C21 103.4(3) . . ?
N3 C10 C8 114.0(3) . . ?
N3 C10 C11 111.8(3) . . ?
N3 C10 C21 104.8(3) . . ?
C12 C11 C10 173.2(4) . . ?
C11 C12 C13 178.1(5) . . ?
C14 C13 C12 120.2(5) . . ?
C18 C13 C12 120.5(5) . . ?
C18 C13 C14 119.3(5) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(6) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(7) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(7) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(8) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.8(7) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
N2 C19 H19A 109.7 . . ?
N2 C19 H19B 109.7 . . ?
N2 C19 C20 109.8(9) . . ?
H19C C19A H19D 109.0 . . ?
C20A C19A H19C 110.9 . . ?
C20A C19A H19D 110.9 . . ?
N2 C19A H19C 110.9 . . ?
N2 C19A H19D 110.9 . . ?
N2 C19A C20A 104(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O2 C21 C10 122.2(3) . . ?
O2 C21 O3 126.6(4) . . ?
O3 C21 C10 111.1(3) . . ?
H22A C22 H22B 109.0 . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C23 C22 O3 103.8(8) . . ?
O3 C22 H22A 111.0 . . ?
O3 C22 H22B 111.0 . . ?
H22C C22A H22D 109.1 . . ?
C23A C22A H22C 111.2 . . ?
C23A C22A H22D 111.2 . . ?
O3 C22A H22C 111.2 . . ?
O3 C22A H22D 111.2 . . ?
O3 C22A C23A 103.0(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O4 C24 N3 124.4(3) . . ?
O4 C24 O5 126.1(3) . . ?
O5 C24 N3 109.5(3) . . ?
C26 C25 C27 111.9(5) . . ?
C26 C25 C28 110.6(4) . . ?
C27 C25 C28 112.0(5) . . ?
O5 C25 C26 110.9(4) . . ?
O5 C25 C27 109.0(3) . . ?
O5 C25 C28 102.0(4) . . ?
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 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 N1 O1 105.1(3) . . ?
C9 N2 C19 122.8(6) . . ?
C9 N2 C19A 131(3) . . ?
C9 N2 H2A 114(3) . . ?
C19 N2 H2A 118(3) . . ?
C19A N2 H2A 115(4) . . ?
C10 N3 H3A 116(3) . . ?
C24 N3 C10 123.5(3) . . ?
C24 N3 H3A 118(3) . . ?
C9 O1 N1 108.3(3) . . ?
C21 O3 C22 110.3(5) . . ?
C21 O3 C22A 123.4(6) . . ?
C24 O5 C25 120.9(3) . . ?

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
C1 H1 N3 0.93 2.87 3.596(5) 135.4 .
C4 H4 O1 0.93 2.83 3.488(5) 128.3 3
C5 H5 O1 0.93 2.94 3.541(5) 123.4 3
C20 H20C O2 0.96 2.57 3.267(8) 129.2 4_645
C22A H22C O1 0.97 2.81 3.506(12) 129.6 1_655
C23 H23B N1 0.96 2.51 3.343(12) 144.8 1_655
C28 H28A O1 0.96 2.74 3.525(7) 140.0 4_655
N2 H2A O4 0.85(2) 2.20(3) 2.882(4) 138(3) .
N3 H3A O2 0.86(2) 2.15(4) 2.601(4) 112(3) .

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
C1 C2 C3 C4 -0.2(8) . . . . ?
C1 C6 C7 C8 -44.2(6) . . . . ?
C1 C6 C7 N1 134.9(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C2 C1 C6 C7 -179.8(4) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C1 0.8(6) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 C8 136.9(4) . . . . ?
C5 C6 C7 N1 -44.0(5) . . . . ?
C6 C1 C2 C3 0.6(8) . . . . ?
C6 C7 C8 C9 178.1(4) . . . . ?
C6 C7 C8 C10 -8.6(6) . . . . ?
C6 C7 N1 O1 -178.6(3) . . . . ?
C7 C8 C9 N2 -179.5(4) . . . . ?
C7 C8 C9 O1 1.0(4) . . . . ?
C7 C8 C10 C11 -140.4(4) . . . . ?
C7 C8 C10 C21 -25.8(5) . . . . ?
C7 C8 C10 N3 93.2(4) . . . . ?
C7 N1 O1 C9 0.0(4) . . . . ?
C8 C7 N1 O1 0.7(4) . . . . ?
C8 C9 N2 C19 173.4(6) . . . . ?
C8 C9 N2 C19A -164(2) . . . . ?
C8 C9 O1 N1 -0.7(4) . . . . ?
C8 C10 C21 O2 133.2(4) . . . . ?
C8 C10 C21 O3 -49.5(4) . . . . ?
C8 C10 N3 C24 68.0(5) . . . . ?
C9 C8 C10 C11 31.5(5) . . . . ?
C9 C8 C10 C21 146.0(4) . . . . ?
C9 C8 C10 N3 -94.9(4) . . . . ?
C10 C8 C9 N2 7.0(7) . . . . ?
C10 C8 C9 O1 -172.5(3) . . . . ?
C10 C21 O3 C22 173.0(5) . . . . ?
C10 C21 O3 C22A -154.6(7) . . . . ?
C11 C10 C21 O2 -108.3(4) . . . . ?
C11 C10 C21 O3 69.0(4) . . . . ?
C11 C10 N3 C24 -57.5(5) . . . . ?
C12 C13 C14 C15 179.1(5) . . . . ?
C12 C13 C18 C17 -178.6(6) . . . . ?
C13 C14 C15 C16 0.2(11) . . . . ?
C14 C13 C18 C17 2.3(10) . . . . ?
C14 C15 C16 C17 1.0(14) . . . . ?
C15 C16 C17 C18 -0.5(15) . . . . ?
C16 C17 C18 C13 -1.2(13) . . . . ?
C18 C13 C14 C15 -1.9(8) . . . . ?
C20 C19 N2 C9 -178.0(7) . . . . ?
C20A C19A N2 C9 -110(4) . . . . ?
C21 C10 N3 C24 -168.8(3) . . . . ?
C23 C22 O3 C21 -169.8(7) . . . . ?
C23A C22A O3 C21 -95.6(12) . . . . ?
C26 C25 O5 C24 62.0(5) . . . . ?
C27 C25 O5 C24 -61.7(5) . . . . ?
C28 C25 O5 C24 179.8(4) . . . . ?
N1 C7 C8 C9 -1.1(4) . . . . ?
N1 C7 C8 C10 172.2(3) . . . . ?
N2 C9 O1 N1 179.8(4) . . . . ?
N3 C10 C21 O2 8.8(5) . . . . ?
N3 C10 C21 O3 -173.8(3) . . . . ?
N3 C24 O5 C25 174.4(3) . . . . ?
O1 C9 N2 C19 -7.1(8) . . . . ?
O1 C9 N2 C19A 16(2) . . . . ?
O2 C21 O3 C22 -9.8(7) . . . . ?
O2 C21 O3 C22A 22.5(9) . . . . ?
O4 C24 N3 C10 -4.6(6) . . . . ?
O4 C24 O5 C25 -5.5(6) . . . . ?
O5 C24 N3 C10 175.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.841
####################################################################### 
# 
# 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_210410_s1_lm
_database_code_depnum_ccdc_archive 'CCDC 2155271'
loop_
_audit_author_name
_audit_author_address
Liminer
;Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-02-28 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H30 I N3 O5'
_chemical_formula_sum            'C28 H30 I N3 O5'
_chemical_formula_weight         615.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3i1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   18.330(2)
_cell_length_b                   10.0441(6)
_cell_length_c                   16.8467(17)
_cell_angle_alpha                90
_cell_angle_beta                 116.711(13)
_cell_angle_gamma                90
_cell_volume                     2770.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4230
_cell_measurement_theta_min      3.3820
_shelx_estimated_absorpt_T_max   0.754
_shelx_estimated_absorpt_T_min   0.679
_exptl_absorpt_coefficient_mu    1.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.018
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   17.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -57.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega   12.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000 -120.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0299464000
_diffrn_orient_matrix_UB_12      0.0143833000
_diffrn_orient_matrix_UB_13      -0.0437418000
_diffrn_orient_matrix_UB_21      0.0292224000
_diffrn_orient_matrix_UB_22      -0.0115310000
_diffrn_orient_matrix_UB_23      -0.0160214000
_diffrn_orient_matrix_UB_31      -0.0111920000
_diffrn_orient_matrix_UB_32      -0.0683098000
_diffrn_orient_matrix_UB_33      -0.0065515000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4161
_reflns_number_total             5654
_reflns_odcompleteness_completeness 83.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         1.217
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+2.0896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1283
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.29547(2) 1.23672(3) 0.33617(2) 0.05922(14) Uani 1 1 d . . . . .
O1 O 0.36307(17) 0.7838(3) 0.59764(18) 0.0540(7) Uani 1 1 d . . . . .
O2 O 0.22932(17) 1.1107(3) 0.55179(18) 0.0626(8) Uani 1 1 d . . . . .
O3 O 0.10073(16) 1.1716(3) 0.45483(19) 0.0574(8) Uani 1 1 d . . . . .
O4 O 0.15069(17) 0.9636(3) 0.25155(18) 0.0572(8) Uani 1 1 d . . . . .
O5 O 0.27607(17) 0.8751(3) 0.30584(18) 0.0538(7) Uani 1 1 d . . . . .
N1 N 0.39617(18) 1.0003(4) 0.5757(2) 0.0464(8) Uani 1 1 d . . . . .
N2 N 0.3012(2) 0.6879(4) 0.5494(2) 0.0549(9) Uani 1 1 d . . . . .
N3 N 0.17271(19) 1.0556(3) 0.4057(2) 0.0454(8) Uani 1 1 d . . . . .
H3 H 0.128159 1.056351 0.356834 0.054 Uiso 1 1 calc R . . . .
C1 C 0.3142(2) 1.0916(4) 0.4325(2) 0.0401(8) Uani 1 1 d . . . . .
C2 C 0.2451(2) 0.9924(4) 0.4069(2) 0.0382(8) Uani 1 1 d . . . . .
C3 C 0.2769(2) 0.8805(4) 0.4719(2) 0.0384(8) Uani 1 1 d . . . . .
C4 C 0.2519(2) 0.7480(4) 0.4757(3) 0.0426(9) Uani 1 1 d . . . . .
C5 C 0.3456(2) 0.8942(4) 0.5485(2) 0.0438(9) Uani 1 1 d . . . . .
C6 C 0.3788(2) 1.1018(4) 0.5125(2) 0.0406(8) Uani 1 1 d . . . . .
C7 C 0.1734(2) 1.1129(4) 0.4787(3) 0.0479(10) Uani 1 1 d . . . . .
C8 C 0.0836(3) 1.2411(4) 0.5217(3) 0.0610(13) Uani 1 1 d . . . . .
C9 C -0.0044(3) 1.2859(7) 0.4650(4) 0.097(2) Uani 1 1 d . . . . .
H9A H -0.006112 1.347319 0.420543 0.145 Uiso 1 1 calc GR . . . .
H9B H -0.024628 1.328615 0.502102 0.145 Uiso 1 1 calc GR . . . .
H9C H -0.037656 1.209818 0.436719 0.145 Uiso 1 1 calc GR . . . .
C10 C 0.1396(4) 1.3577(5) 0.5593(4) 0.0846(17) Uani 1 1 d . . . . .
H10A H 0.194893 1.326735 0.591017 0.127 Uiso 1 1 calc GR . . . .
H10B H 0.124829 1.405734 0.599219 0.127 Uiso 1 1 calc GR . . . .
H10C H 0.135089 1.415384 0.511897 0.127 Uiso 1 1 calc GR . . . .
C11 C 0.0878(4) 1.1435(6) 0.5915(4) 0.0844(16) Uani 1 1 d . . . . .
H11A H 0.052552 1.069357 0.563374 0.127 Uiso 1 1 calc GR . . . .
H11B H 0.070661 1.186462 0.631178 0.127 Uiso 1 1 calc GR . . . .
H11C H 0.142936 1.112468 0.624354 0.127 Uiso 1 1 calc GR . . . .
C12 C 0.2168(2) 0.9419(4) 0.3111(2) 0.0422(9) Uani 1 1 d . . . . .
C13 C 0.2611(3) 0.8244(5) 0.2191(3) 0.0676(13) Uani 1 1 d . . . . .
H13A H 0.311030 0.829505 0.212779 0.081 Uiso 1 1 calc R . . . .
H13B H 0.220380 0.879492 0.173274 0.081 Uiso 1 1 calc R . . . .
C14 C 0.2327(4) 0.6871(6) 0.2069(4) 0.0837(16) Uani 1 1 d . . . . .
H14A H 0.225244 0.655718 0.149954 0.125 Uiso 1 1 calc GR . . . .
H14B H 0.181671 0.682507 0.209949 0.125 Uiso 1 1 calc GR . . . .
H14C H 0.272375 0.632607 0.252823 0.125 Uiso 1 1 calc GR . . . .
C15 C 0.1820(2) 0.6722(4) 0.4103(3) 0.0447(9) Uani 1 1 d . . . . .
C16 C 0.1059(3) 0.7311(4) 0.3647(4) 0.0631(13) Uani 1 1 d . . . . .
H16 H 0.098455 0.819721 0.375358 0.076 Uiso 1 1 calc R . . . .
C17 C 0.0416(3) 0.6590(5) 0.3042(4) 0.0860(18) Uani 1 1 d . . . . .
H17 H -0.009205 0.699210 0.273655 0.103 Uiso 1 1 calc R . . . .
C18 C 0.0513(3) 0.5291(5) 0.2881(4) 0.0826(17) Uani 1 1 d . . . . .
H18 H 0.007173 0.480575 0.247224 0.099 Uiso 1 1 calc R . . . .
C19 C 0.1258(3) 0.4705(5) 0.3320(4) 0.0768(15) Uani 1 1 d . . . . .
H19 H 0.132429 0.381755 0.320921 0.092 Uiso 1 1 calc R . . . .
C20 C 0.1912(3) 0.5411(4) 0.3926(3) 0.0612(12) Uani 1 1 d . . . . .
H20 H 0.241946 0.500280 0.421805 0.073 Uiso 1 1 calc R . . . .
C21 C 0.4563(2) 1.0114(5) 0.6698(3) 0.0587(12) Uani 1 1 d . . . . .
H21A H 0.433246 0.975000 0.706872 0.070 Uiso 1 1 calc R . . . .
H21B H 0.468692 1.104565 0.685137 0.070 Uiso 1 1 calc R . . . .
C22 C 0.5347(3) 0.9372(7) 0.6879(4) 0.107(2) Uani 1 1 d . . . . .
H22A H 0.551962 0.960939 0.643711 0.160 Uiso 1 1 calc GR . . . .
H22B H 0.525064 0.843071 0.685669 0.160 Uiso 1 1 calc GR . . . .
H22C H 0.576557 0.960983 0.745672 0.160 Uiso 1 1 calc GR . . . .
C23 C 0.4350(2) 1.2168(4) 0.5418(3) 0.0437(9) Uani 1 1 d . . . . .
C24 C 0.4101(3) 1.3335(4) 0.5657(3) 0.0559(11) Uani 1 1 d . . . . .
H24 H 0.358286 1.339073 0.562874 0.067 Uiso 1 1 calc R . . . .
C25 C 0.4615(3) 1.4408(5) 0.5937(3) 0.0636(13) Uani 1 1 d . . . . .
H25 H 0.444313 1.519428 0.609174 0.076 Uiso 1 1 calc R . . . .
C26 C 0.5382(3) 1.4331(5) 0.5989(3) 0.0643(13) Uani 1 1 d . . . . .
H26 H 0.573237 1.505774 0.619000 0.077 Uiso 1 1 calc R . . . .
C27 C 0.5633(3) 1.3182(5) 0.5747(3) 0.0621(12) Uani 1 1 d . . . . .
H27 H 0.615011 1.313500 0.577366 0.075 Uiso 1 1 calc R . . . .
C28 C 0.5120(2) 1.2100(4) 0.5464(3) 0.0519(10) Uani 1 1 d . . . . .
H28 H 0.529177 1.131982 0.530230 0.062 Uiso 1 1 calc R . . . .


_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
I1 C1 2.092(4) . ?
O1 N2 1.430(5) . ?
O1 C5 1.334(5) . ?
O2 C7 1.197(4) . ?
O3 C7 1.343(4) . ?
O3 C8 1.474(5) . ?
O4 C12 1.195(4) . ?
O5 C12 1.313(4) . ?
O5 C13 1.453(5) . ?
N1 C5 1.350(5) . ?
N1 C6 1.403(5) . ?
N1 C21 1.472(5) . ?
N2 C4 1.310(5) . ?
N3 C2 1.462(5) . ?
N3 C7 1.354(5) . ?
C1 C2 1.513(5) . ?
C1 C6 1.340(5) . ?
C2 C3 1.493(5) . ?
C2 C12 1.542(5) . ?
C3 C4 1.418(5) . ?
C3 C5 1.346(5) . ?
C4 C15 1.471(6) . ?
C6 C23 1.477(5) . ?
C8 C9 1.526(7) . ?
C8 C10 1.498(7) . ?
C8 C11 1.505(7) . ?
C13 C14 1.455(8) . ?
C15 C16 1.387(6) . ?
C15 C20 1.377(6) . ?
C16 C17 1.368(7) . ?
C17 C18 1.360(7) . ?
C18 C19 1.360(7) . ?
C19 C20 1.372(6) . ?
C21 C22 1.523(7) . ?
C23 C24 1.382(6) . ?
C23 C28 1.379(6) . ?
C24 C25 1.369(6) . ?
C25 C26 1.370(7) . ?
C26 C27 1.370(7) . ?
C27 C28 1.375(6) . ?

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
C5 O1 N2 107.4(3) . . ?
C7 O3 C8 120.2(3) . . ?
C12 O5 C13 117.3(3) . . ?
C5 N1 C6 115.4(3) . . ?
C5 N1 C21 119.5(3) . . ?
C6 N1 C21 124.5(3) . . ?
C4 N2 O1 105.2(3) . . ?
C7 N3 C2 122.3(3) . . ?
C2 C1 I1 114.4(2) . . ?
C6 C1 I1 119.3(3) . . ?
C6 C1 C2 125.8(3) . . ?
N3 C2 C1 110.9(3) . . ?
N3 C2 C3 112.9(3) . . ?
N3 C2 C12 104.6(3) . . ?
C1 C2 C12 111.1(3) . . ?
C3 C2 C1 106.6(3) . . ?
C3 C2 C12 110.9(3) . . ?
C4 C3 C2 135.4(3) . . ?
C5 C3 C2 121.0(3) . . ?
C5 C3 C4 103.6(3) . . ?
N2 C4 C3 112.1(4) . . ?
N2 C4 C15 118.0(4) . . ?
C3 C4 C15 129.9(3) . . ?
O1 C5 N1 120.6(3) . . ?
O1 C5 C3 111.7(4) . . ?
C3 C5 N1 127.6(4) . . ?
N1 C6 C23 115.3(3) . . ?
C1 C6 N1 120.3(4) . . ?
C1 C6 C23 124.3(4) . . ?
O2 C7 O3 126.3(4) . . ?
O2 C7 N3 125.5(4) . . ?
O3 C7 N3 108.2(3) . . ?
O3 C8 C9 100.9(4) . . ?
O3 C8 C10 110.6(4) . . ?
O3 C8 C11 109.6(4) . . ?
C10 C8 C9 111.4(4) . . ?
C10 C8 C11 113.2(5) . . ?
C11 C8 C9 110.5(5) . . ?
O4 C12 O5 126.4(4) . . ?
O4 C12 C2 123.8(4) . . ?
O5 C12 C2 109.8(3) . . ?
O5 C13 C14 111.6(4) . . ?
C16 C15 C4 121.0(4) . . ?
C20 C15 C4 120.5(4) . . ?
C20 C15 C16 118.6(4) . . ?
C17 C16 C15 120.1(4) . . ?
C18 C17 C16 120.7(5) . . ?
C17 C18 C19 119.7(5) . . ?
C18 C19 C20 120.6(5) . . ?
C19 C20 C15 120.3(4) . . ?
N1 C21 C22 111.2(4) . . ?
C24 C23 C6 119.2(4) . . ?
C28 C23 C6 121.5(4) . . ?
C28 C23 C24 119.3(4) . . ?
C25 C24 C23 120.1(4) . . ?
C24 C25 C26 120.4(4) . . ?
C27 C26 C25 120.0(4) . . ?
C26 C27 C28 120.0(4) . . ?
C27 C28 C23 120.2(4) . . ?

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
I1 C1 C2 N3 -70.0(3) . . . . ?
I1 C1 C2 C3 166.8(2) . . . . ?
I1 C1 C2 C12 45.9(4) . . . . ?
I1 C1 C6 N1 -175.0(3) . . . . ?
I1 C1 C6 C23 6.1(5) . . . . ?
O1 N2 C4 C3 -0.5(4) . . . . ?
O1 N2 C4 C15 178.6(3) . . . . ?
N1 C6 C23 C24 -103.0(4) . . . . ?
N1 C6 C23 C28 76.5(5) . . . . ?
N2 O1 C5 N1 -176.8(3) . . . . ?
N2 O1 C5 C3 0.7(4) . . . . ?
N2 C4 C15 C16 139.2(4) . . . . ?
N2 C4 C15 C20 -41.2(6) . . . . ?
N3 C2 C3 C4 74.0(5) . . . . ?
N3 C2 C3 C5 -106.3(4) . . . . ?
N3 C2 C12 O4 5.1(5) . . . . ?
N3 C2 C12 O5 -175.9(3) . . . . ?
C1 C2 C3 C4 -164.1(4) . . . . ?
C1 C2 C3 C5 15.7(4) . . . . ?
C1 C2 C12 O4 -114.5(4) . . . . ?
C1 C2 C12 O5 64.4(4) . . . . ?
C1 C6 C23 C24 76.0(5) . . . . ?
C1 C6 C23 C28 -104.5(5) . . . . ?
C2 N3 C7 O2 -5.4(7) . . . . ?
C2 N3 C7 O3 174.8(3) . . . . ?
C2 C1 C6 N1 13.4(6) . . . . ?
C2 C1 C6 C23 -165.5(3) . . . . ?
C2 C3 C4 N2 -179.3(4) . . . . ?
C2 C3 C4 C15 1.7(7) . . . . ?
C2 C3 C5 O1 179.3(3) . . . . ?
C2 C3 C5 N1 -3.5(6) . . . . ?
C3 C2 C12 O4 127.1(4) . . . . ?
C3 C2 C12 O5 -53.9(4) . . . . ?
C3 C4 C15 C16 -41.8(6) . . . . ?
C3 C4 C15 C20 137.8(4) . . . . ?
C4 C3 C5 O1 -0.9(4) . . . . ?
C4 C3 C5 N1 176.3(4) . . . . ?
C4 C15 C16 C17 -180.0(5) . . . . ?
C4 C15 C20 C19 179.5(4) . . . . ?
C5 O1 N2 C4 -0.1(4) . . . . ?
C5 N1 C6 C1 2.1(5) . . . . ?
C5 N1 C6 C23 -178.9(3) . . . . ?
C5 N1 C21 C22 86.1(5) . . . . ?
C5 C3 C4 N2 0.9(4) . . . . ?
C5 C3 C4 C15 -178.1(4) . . . . ?
C6 N1 C5 O1 170.0(3) . . . . ?
C6 N1 C5 C3 -7.0(6) . . . . ?
C6 N1 C21 C22 -103.1(5) . . . . ?
C6 C1 C2 N3 102.1(4) . . . . ?
C6 C1 C2 C3 -21.2(5) . . . . ?
C6 C1 C2 C12 -142.1(4) . . . . ?
C6 C23 C24 C25 179.5(4) . . . . ?
C6 C23 C28 C27 -179.4(4) . . . . ?
C7 O3 C8 C9 -178.4(4) . . . . ?
C7 O3 C8 C10 63.6(5) . . . . ?
C7 O3 C8 C11 -61.9(6) . . . . ?
C7 N3 C2 C1 -60.1(5) . . . . ?
C7 N3 C2 C3 59.5(5) . . . . ?
C7 N3 C2 C12 -179.9(4) . . . . ?
C8 O3 C7 O2 -0.6(7) . . . . ?
C8 O3 C7 N3 179.2(4) . . . . ?
C12 O5 C13 C14 -94.8(5) . . . . ?
C12 C2 C3 C4 -43.0(6) . . . . ?
C12 C2 C3 C5 136.7(4) . . . . ?
C13 O5 C12 O4 1.2(6) . . . . ?
C13 O5 C12 C2 -177.7(3) . . . . ?
C15 C16 C17 C18 0.3(9) . . . . ?
C16 C15 C20 C19 -0.9(7) . . . . ?
C16 C17 C18 C19 -0.6(10) . . . . ?
C17 C18 C19 C20 0.2(10) . . . . ?
C18 C19 C20 C15 0.6(8) . . . . ?
C20 C15 C16 C17 0.4(8) . . . . ?
C21 N1 C5 O1 -18.4(5) . . . . ?
C21 N1 C5 C3 164.6(4) . . . . ?
C21 N1 C6 C1 -169.0(4) . . . . ?
C21 N1 C6 C23 10.0(5) . . . . ?
C23 C24 C25 C26 -0.6(7) . . . . ?
C24 C23 C28 C27 0.1(6) . . . . ?
C24 C25 C26 C27 1.2(7) . . . . ?
C25 C26 C27 C28 -1.0(7) . . . . ?
C26 C27 C28 C23 0.4(7) . . . . ?
C28 C23 C24 C25 0.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
