# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_202112355a
_database_code_depnum_ccdc_archive 'CCDC 2312826'
loop_
_audit_author_name
_audit_author_address
'YONG YOU'
;Chengdu University
China
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_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         'C30 H24 Cl N3 O4, C2 H6 O S'
_chemical_formula_sum            'C32 H30 Cl N3 O5 S'
_chemical_formula_weight         604.10
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2Cl1
_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'
Cl Cl 0.3639 0.7018 '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'
S S 0.3331 0.5567 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.0863(5)
_cell_length_b                   16.8287(11)
_cell_length_c                   9.8355(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.730(5)
_cell_angle_gamma                90
_cell_volume                     1503.27(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2730
_cell_measurement_theta_min      4.4900
_shelx_estimated_absorpt_T_max   0.814
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    2.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90827
_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    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10152
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.690
_diffrn_reflns_theta_min         4.498
_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 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  -6.00   1.00    1.00    --  -33.50 -77.00   0.00   94
  2  ω    -27.00  51.00   1.00    1.00    --   36.47 -57.00-150.00   78
  3  ω     66.00 106.00   1.00    1.00    --   36.47 178.00  60.00   40
  4  ω     46.00  77.00   1.00    1.00    --   36.47 -99.00-120.00   31
  5  ω     37.00  76.00   1.00    1.00    --   36.47 -99.00  30.00   39
  6  ω    -32.00  22.00   1.00    1.00    --   36.47 -57.00 -60.00   54
  7  ω     18.00  70.00   1.00    1.00    --   36.47 -19.00 -90.00   52
  8  ω     48.00  93.00   1.00    3.50    --  108.00 -94.00 120.00   45
  9  ω    124.00 173.00   1.00    3.50    --  108.00  45.00  60.00   49
 10  ω    124.00 175.00   1.00    3.50    --  108.00 111.00-180.00   51
 11  ω    100.00 160.00   1.00    3.50    --  108.00 111.00   0.00   60
 12  ω     79.00 124.00   1.00    3.50    --  108.00 -45.00  90.00   45
 13  ω     79.00 105.00   1.00    3.50    --  108.00 -94.00  60.00   26
 14  ω    106.00 139.00   1.00    3.50    --  108.00 111.00 -30.00   33
 15  ω     37.00 133.00   1.00    3.50    --  108.00 -30.00-120.00   96
 16  ω     52.00 136.00   1.00    3.50    --  108.00 -77.00-120.00   84
 17  ω     23.00  51.00   1.00    2.00    --   36.47  57.00-120.00   28
 18  ω     18.00  50.00   1.00    2.00    --   36.47  57.00 150.00   32
 19  ω     69.00  96.00   1.00    2.00    --   36.47  19.00  60.00   27
 20  ω     53.00  79.00   1.00    2.00    --   36.47  57.00 -90.00   26
 21  ω     29.00  56.00   1.00    2.00    --   36.47  37.00  60.00   27
 22  ω     16.00  49.00   1.00    2.00    --   36.47  77.00 120.00   33
 23  ω     59.00  85.00   1.00    2.00    --   36.47  57.00 150.00   26
 24  ω     24.00  50.00   1.00    2.00    --   36.47  57.00-150.00   26
 25  ω     20.00  89.00   1.00    2.00    --   36.47  57.00  90.00   69
 26  ω     74.00 100.00   1.00    2.00    --   36.47 178.00 -60.00   26
 27  ω     57.00  82.00   1.00    2.00    --   36.47 178.00-120.00   25
 28  ω     18.00  62.00   1.00    2.00    --   36.47  57.00 -30.00   44
 29  ω     91.00 117.00   1.00    3.50    --  108.00  45.00  60.00   26
 30  ω     83.00 131.00   1.00    3.50    --  108.00  30.00 150.00   48
 31  ω     79.00 105.00   1.00    3.50    --  108.00  77.00  90.00   26
 32  ω     84.00 110.00   1.00    3.50    --  108.00  30.00 120.00   26
 33  ω     84.00 110.00   1.00    3.50    --  108.00  30.00  90.00   26
 34  ω     88.00 113.00   1.00    3.50    --  108.00  61.00 150.00   25
 35  ω    149.00 177.00   1.00    3.50    --  108.00  77.00  30.00   28
 36  ω     88.00 113.00   1.00    3.50    --  108.00  61.00  90.00   25
 37  ω     84.00 127.00   1.00    3.50    --  108.00  30.00-180.00   43
 38  ω     88.00 114.00   1.00    3.50    --  108.00  61.00 120.00   26
 39  ω     85.00 111.00   1.00    3.50    --  108.00  30.00  60.00   26
;
_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      -0.0789964000
_diffrn_orient_matrix_UB_12      -0.0037626000
_diffrn_orient_matrix_UB_13      0.1363632000
_diffrn_orient_matrix_UB_21      0.1447634000
_diffrn_orient_matrix_UB_22      0.0222299000
_diffrn_orient_matrix_UB_23      0.0762679000
_diffrn_orient_matrix_UB_31      -0.0396698000
_diffrn_orient_matrix_UB_32      0.0886668000
_diffrn_orient_matrix_UB_33      -0.0132681000
_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         0.685
_reflns_Friedel_fraction_full    0.754
_reflns_Friedel_fraction_max     0.716
_reflns_number_gt                4197
_reflns_number_total             4993
_reflns_odcompleteness_completeness 99.96
_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         0.353
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.052
_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)+(0.0580P)²+0.2896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S1A-C31A
 1.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5) \\sim Ueq, Uanis(O5A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C31A) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(S1) = Uanis(S1A)
Uanis(O5) = Uanis(O5A)
Uanis(C31) = Uanis(C31A)
Uanis(C32) = Uanis(C32A)
4. Others
 Sof(C31A)=Sof(H31d)=Sof(H31e)=Sof(H31f)=Sof(C32A)=Sof(H32d)=Sof(H32e)=
 Sof(H32f)=Sof(O5A)=Sof(S1A)=1-FVAR(1)
 Sof(C31)=Sof(H31a)=Sof(H31b)=Sof(H31c)=Sof(C32)=Sof(H32a)=Sof(H32b)=Sof(H32c)=
 Sof(O5)=Sof(S1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
5.b Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c), C31(H31a,H31b,
 H31c), C32(H32a,H32b,H32c), C31A(H31d,H31e,H31f), C32A(H32d,H32e,H32f)
;
_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 0.5695(6) 0.3791(3) -0.3327(5) 0.0557(13) Uani 1 1 d . . . . .
H1 H 0.6360 0.4013 -0.3919 0.067 Uiso 1 1 calc R . . . .
C2 C 0.4264(6) 0.3652(4) -0.3776(5) 0.0611(14) Uani 1 1 d . . . . .
H2 H 0.3958 0.3772 -0.4664 0.073 Uiso 1 1 calc R . . . .
C3 C 0.3307(5) 0.3332(3) -0.2875(5) 0.0543(12) Uani 1 1 d . . . . .
C4 C 0.3694(5) 0.3137(3) -0.1559(4) 0.0474(10) Uani 1 1 d . . . . .
H4 H 0.3009 0.2925 -0.0977 0.057 Uiso 1 1 calc R . . . .
C5 C 0.5153(5) 0.3268(3) -0.1119(4) 0.0425(10) Uani 1 1 d . . . . .
C6 C 0.6159(5) 0.3605(3) -0.2007(4) 0.0444(10) Uani 1 1 d . . . . .
C7 C 0.7664(5) 0.3806(3) -0.1516(4) 0.0476(11) Uani 1 1 d . . . . .
C8 C 0.7109(5) 0.2986(3) 0.0492(4) 0.0410(10) Uani 1 1 d . . . . .
C9 C 0.7593(4) 0.3073(3) 0.2044(4) 0.0383(9) Uani 1 1 d . . . . .
C10 C 0.9075(4) 0.3485(3) 0.1903(4) 0.0395(9) Uani 1 1 d . . . . .
C11 C 0.9303(5) 0.3689(3) 0.0558(4) 0.0430(10) Uani 1 1 d . . . . .
C12 C 1.0622(5) 0.4004(3) 0.0165(5) 0.0541(12) Uani 1 1 d . . . . .
H12 H 1.0778 0.4129 -0.0740 0.065 Uiso 1 1 calc R . . . .
C13 C 1.1713(5) 0.4132(3) 0.1160(6) 0.0609(14) Uani 1 1 d . . . . .
H13 H 1.2616 0.4341 0.0918 0.073 Uiso 1 1 calc R . . . .
C14 C 1.1472(5) 0.3952(3) 0.2511(5) 0.0547(12) Uani 1 1 d . . . . .
H14 H 1.2208 0.4054 0.3166 0.066 Uiso 1 1 calc R . . . .
C15 C 1.0154(5) 0.3624(3) 0.2899(5) 0.0488(11) Uani 1 1 d . . . . .
H15 H 0.9997 0.3499 0.3804 0.059 Uiso 1 1 calc R . . . .
C16 C 0.7796(5) 0.2209(3) 0.2463(4) 0.0402(9) Uani 1 1 d . . . . .
C17 C 0.7805(5) 0.1759(3) 0.1310(5) 0.0459(10) Uani 1 1 d . . . . .
C18 C 0.8083(6) 0.0940(3) 0.1323(5) 0.0578(13) Uani 1 1 d . . . . .
H18 H 0.8107 0.0650 0.0519 0.069 Uiso 1 1 calc R . . . .
C19 C 0.8318(7) 0.0585(3) 0.2549(6) 0.0640(14) Uani 1 1 d . . . . .
H19 H 0.8503 0.0042 0.2580 0.077 Uiso 1 1 calc R . . . .
C20 C 0.8287(6) 0.1016(3) 0.3779(5) 0.0552(12) Uani 1 1 d . . . . .
C21 C 0.8021(5) 0.1854(3) 0.3756(5) 0.0443(10) Uani 1 1 d . . . . .
C22 C 0.8015(5) 0.2265(3) 0.5014(5) 0.0526(12) Uani 1 1 d . . . . .
H22 H 0.7884 0.2813 0.5017 0.063 Uiso 1 1 calc R . . . .
C23 C 0.8201(7) 0.1869(4) 0.6231(5) 0.0657(15) Uani 1 1 d . . . . .
H23 H 0.8172 0.2149 0.7045 0.079 Uiso 1 1 calc R . . . .
C24 C 0.8432(8) 0.1050(4) 0.6249(7) 0.0808(19) Uani 1 1 d . . . . .
H24 H 0.8551 0.0785 0.7075 0.097 Uiso 1 1 calc R . . . .
C25 C 0.8484(7) 0.0641(4) 0.5071(6) 0.0716(17) Uani 1 1 d . . . . .
H25 H 0.8653 0.0096 0.5103 0.086 Uiso 1 1 calc R . . . .
C26 C 0.6073(5) 0.4243(3) 0.2739(4) 0.0426(10) Uani 1 1 d . . . . .
C27 C 0.6723(6) 0.5519(3) 0.1708(6) 0.0583(13) Uani 1 1 d . . . . .
C28 C 0.8027(8) 0.5721(4) 0.0825(8) 0.088(2) Uani 1 1 d . . . . .
H28A H 0.8930 0.5612 0.1323 0.132 Uiso 1 1 calc GR . . . .
H28B H 0.7990 0.6273 0.0583 0.132 Uiso 1 1 calc GR . . . .
H28C H 0.7980 0.5403 0.0014 0.132 Uiso 1 1 calc GR . . . .
C29 C 0.6811(13) 0.5957(5) 0.3029(9) 0.119(3) Uani 1 1 d . . . . .
H29A H 0.5931 0.5864 0.3520 0.178 Uiso 1 1 calc GR . . . .
H29B H 0.6911 0.6516 0.2857 0.178 Uiso 1 1 calc GR . . . .
H29C H 0.7649 0.5774 0.3558 0.178 Uiso 1 1 calc GR . . . .
C30 C 0.5281(8) 0.5630(5) 0.0918(8) 0.093(2) Uani 1 1 d . . . . .
H30A H 0.5296 0.5326 0.0093 0.140 Uiso 1 1 calc GR . . . .
H30B H 0.5149 0.6182 0.0701 0.140 Uiso 1 1 calc GR . . . .
H30C H 0.4483 0.5453 0.1459 0.140 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.14941(16) 0.31459(12) -0.34245(15) 0.0797(5) Uani 1 1 d . . . . .
N1 N 0.8036(4) 0.3509(2) -0.0252(3) 0.0426(8) Uani 1 1 d . . . . .
N2 N 0.5606(4) 0.3109(3) 0.0209(4) 0.0446(9) Uani 1 1 d . . . . .
H2A H 0.501(5) 0.288(3) 0.076(4) 0.031(11) Uiso 1 1 d . . . . .
N3 N 0.6539(4) 0.3473(2) 0.2881(4) 0.0407(8) Uani 1 1 d . . . . .
H3 H 0.586(6) 0.315(4) 0.316(5) 0.063(16) Uiso 1 1 d . . . . .
O1 O 0.8498(4) 0.4222(3) -0.2160(4) 0.0672(11) Uani 1 1 d . . . . .
O2 O 0.7536(4) 0.2165(2) 0.0127(3) 0.0511(8) Uani 1 1 d . . . . .
O3 O 0.4998(4) 0.4492(2) 0.3299(4) 0.0644(10) Uani 1 1 d . . . . .
O4 O 0.6946(3) 0.46601(19) 0.1943(3) 0.0496(8) Uani 1 1 d . . . . .
C31 C 0.8254(14) 0.6598(11) 0.6901(17) 0.110(5) Uani 0.721(4) 1 d . U P A 1
H31A H 0.8720 0.6973 0.7510 0.165 Uiso 0.721(4) 1 calc GR . P A 1
H31B H 0.8710 0.6621 0.6034 0.165 Uiso 0.721(4) 1 calc GR . P A 1
H31C H 0.8359 0.6072 0.7270 0.165 Uiso 0.721(4) 1 calc GR . P A 1
C32 C 0.574(2) 0.5847(11) 0.6915(15) 0.089(4) Uani 0.721(4) 1 d . . P A 1
H32A H 0.6330 0.5590 0.7611 0.134 Uiso 0.721(4) 1 calc GR . P A 1
H32B H 0.5817 0.5561 0.6076 0.134 Uiso 0.721(4) 1 calc GR . P A 1
H32C H 0.4731 0.5856 0.7177 0.134 Uiso 0.721(4) 1 calc GR . P A 1
O5 O 0.593(2) 0.7262(14) 0.7951(18) 0.142(6) Uani 0.721(4) 1 d . U P A 1
S1 S 0.6371(3) 0.68303(16) 0.6697(4) 0.0943(8) Uani 0.721(4) 1 d . . P A 1
C31A C 0.798(4) 0.679(3) 0.631(4) 0.110(5) Uani 0.279(4) 1 d D U P A 2
H31D H 0.7505 0.7088 0.5593 0.165 Uiso 0.279(4) 1 calc GR . P A 2
H31E H 0.8322 0.6294 0.5965 0.165 Uiso 0.279(4) 1 calc GR . P A 2
H31F H 0.8809 0.7090 0.6674 0.165 Uiso 0.279(4) 1 calc GR . P A 2
C32A C 0.566(7) 0.599(4) 0.641(5) 0.089(4) Uani 0.279(4) 1 d . . P A 2
H32D H 0.4892 0.5717 0.6866 0.134 Uiso 0.279(4) 1 calc GR . P A 2
H32E H 0.6311 0.5602 0.6020 0.134 Uiso 0.279(4) 1 calc GR . P A 2
H32F H 0.5244 0.6313 0.5695 0.134 Uiso 0.279(4) 1 calc GR . P A 2
O5A O 0.599(7) 0.732(4) 0.743(6) 0.142(6) Uani 0.279(4) 1 d . U P A 2
S1A S 0.6713(8) 0.6614(4) 0.7631(10) 0.0943(8) Uani 0.279(4) 1 d D . P A 2


_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 1.381(7) . ?
C1 C6 1.388(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(8) . ?
C3 C4 1.370(6) . ?
C3 Cl1 1.747(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(6) . ?
C5 C6 1.403(6) . ?
C5 N2 1.384(5) . ?
C6 C7 1.476(6) . ?
C7 N1 1.373(5) . ?
C7 O1 1.222(6) . ?
C8 C9 1.583(5) . ?
C8 N1 1.435(5) . ?
C8 N2 1.401(6) . ?
C8 O2 1.481(6) . ?
C9 C10 1.525(6) . ?
C9 C16 1.521(6) . ?
C9 N3 1.448(6) . ?
C10 C11 1.388(6) . ?
C10 C15 1.384(6) . ?
C11 C12 1.377(6) . ?
C11 N1 1.413(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(6) . ?
C16 C21 1.414(6) . ?
C17 C18 1.400(7) . ?
C17 O2 1.365(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.412(8) . ?
C20 C21 1.431(7) . ?
C20 C25 1.426(7) . ?
C21 C22 1.417(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.394(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.351(9) . ?
C25 H25 0.9300 . ?
C26 N3 1.369(6) . ?
C26 O3 1.210(5) . ?
C26 O4 1.331(5) . ?
C27 C28 1.529(9) . ?
C27 C29 1.494(9) . ?
C27 C30 1.514(8) . ?
C27 O4 1.477(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N2 H2A 0.87(5) . ?
N3 H3 0.87(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 S1 1.761(13) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C32 S1 1.766(18) . ?
O5 S1 1.496(11) . ?
C31A H31D 0.9600 . ?
C31A H31E 0.9600 . ?
C31A H31F 0.9600 . ?
C31A S1A 1.79(2) . ?
C32A H32D 0.9600 . ?
C32A H32E 0.9600 . ?
C32A H32F 0.9600 . ?
C32A S1A 1.85(6) . ?
O5A S1A 1.36(8) . ?

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 119.4 . . ?
C2 C1 C6 121.1(5) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 Cl1 118.7(4) . . ?
C4 C3 C2 123.7(5) . . ?
C4 C3 Cl1 117.5(4) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.9(4) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 120.0(4) . . ?
N2 C5 C4 120.9(4) . . ?
N2 C5 C6 119.0(4) . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 C7 120.4(4) . . ?
C5 C6 C7 120.2(4) . . ?
N1 C7 C6 114.4(4) . . ?
O1 C7 C6 123.0(4) . . ?
O1 C7 N1 122.5(4) . . ?
N1 C8 C9 106.6(3) . . ?
N1 C8 O2 106.7(4) . . ?
N2 C8 C9 114.8(4) . . ?
N2 C8 N1 113.0(4) . . ?
N2 C8 O2 110.6(4) . . ?
O2 C8 C9 104.6(3) . . ?
C10 C9 C8 100.1(3) . . ?
C16 C9 C8 101.6(3) . . ?
C16 C9 C10 111.1(3) . . ?
N3 C9 C8 115.0(3) . . ?
N3 C9 C10 116.2(4) . . ?
N3 C9 C16 111.6(3) . . ?
C11 C10 C9 110.9(4) . . ?
C15 C10 C9 128.4(4) . . ?
C15 C10 C11 120.7(4) . . ?
C10 C11 N1 110.0(4) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 N1 128.7(4) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.1(5) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(5) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 120.9(5) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 H15 120.9 . . ?
C14 C15 C10 118.2(4) . . ?
C14 C15 H15 120.9 . . ?
C17 C16 C9 108.0(4) . . ?
C17 C16 C21 120.6(4) . . ?
C21 C16 C9 131.3(4) . . ?
C16 C17 C18 123.0(4) . . ?
C16 C17 O2 115.2(4) . . ?
O2 C17 C18 121.9(4) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 C17 117.7(5) . . ?
C19 C18 H18 121.1 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.9(5) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 120.1(5) . . ?
C19 C20 C25 122.0(5) . . ?
C25 C20 C21 117.9(5) . . ?
C16 C21 C20 116.7(4) . . ?
C16 C21 C22 125.1(4) . . ?
C22 C21 C20 118.2(4) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.3(5) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.3(6) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 118.9 . . ?
C24 C25 C20 122.1(6) . . ?
C24 C25 H25 118.9 . . ?
O3 C26 N3 122.2(4) . . ?
O3 C26 O4 126.0(4) . . ?
O4 C26 N3 111.8(4) . . ?
C29 C27 C28 111.2(6) . . ?
C29 C27 C30 114.1(7) . . ?
C30 C27 C28 110.8(5) . . ?
O4 C27 C28 101.6(5) . . ?
O4 C27 C29 110.1(5) . . ?
O4 C27 C30 108.3(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 N1 C8 123.6(4) . . ?
C7 N1 C11 127.4(4) . . ?
C11 N1 C8 108.9(3) . . ?
C5 N2 C8 118.5(4) . . ?
C5 N2 H2A 120(3) . . ?
C8 N2 H2A 116(3) . . ?
C9 N3 H3 113(4) . . ?
C26 N3 C9 126.2(4) . . ?
C26 N3 H3 113(4) . . ?
C17 O2 C8 107.6(3) . . ?
C26 O4 C27 121.8(4) . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
S1 C31 H31A 109.5 . . ?
S1 C31 H31B 109.5 . . ?
S1 C31 H31C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
S1 C32 H32A 109.5 . . ?
S1 C32 H32B 109.5 . . ?
S1 C32 H32C 109.5 . . ?
C31 S1 C32 95.5(9) . . ?
O5 S1 C31 107.2(11) . . ?
O5 S1 C32 105.1(11) . . ?
H31D C31A H31E 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
S1A C31A H31D 109.5 . . ?
S1A C31A H31E 109.5 . . ?
S1A C31A H31F 109.5 . . ?
H32D C32A H32E 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 109.5 . . ?
S1A C32A H32D 109.5 . . ?
S1A C32A H32E 109.5 . . ?
S1A C32A H32F 109.5 . . ?
C31A S1A C32A 87(2) . . ?
O5A S1A C31A 94(3) . . ?
O5A S1A C32A 100(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
N2 H2A O5 0.87(5) 1.87(5) 2.723(12) 168(4) 2_646
N2 H2A O5A 0.87(5) 2.23(6) 3.08(4) 164(4) 2_646
N3 H3 O5 0.87(6) 2.45(6) 3.12(3) 135(5) 2_646
N3 H3 O5A 0.87(6) 2.26(10) 3.02(7) 146(5) 2_646

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 -0.5(9) . . . . ?
C1 C2 C3 Cl1 -179.7(4) . . . . ?
C1 C6 C7 N1 -172.8(4) . . . . ?
C1 C6 C7 O1 9.2(8) . . . . ?
C2 C1 C6 C5 0.1(8) . . . . ?
C2 C1 C6 C7 -175.9(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C3 C4 C5 N2 177.9(5) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
C4 C5 C6 C7 174.9(5) . . . . ?
C4 C5 N2 C8 158.5(5) . . . . ?
C5 C6 C7 N1 11.1(7) . . . . ?
C5 C6 C7 O1 -166.8(5) . . . . ?
C6 C1 C2 C3 0.7(8) . . . . ?
C6 C5 N2 C8 -24.9(7) . . . . ?
C6 C7 N1 C8 5.5(7) . . . . ?
C6 C7 N1 C11 -170.6(4) . . . . ?
C8 C9 C10 C11 6.7(5) . . . . ?
C8 C9 C10 C15 -169.8(5) . . . . ?
C8 C9 C16 C17 13.2(4) . . . . ?
C8 C9 C16 C21 -169.8(4) . . . . ?
C8 C9 N3 C26 -62.6(6) . . . . ?
C9 C8 N1 C7 -157.2(4) . . . . ?
C9 C8 N1 C11 19.6(5) . . . . ?
C9 C8 N2 C5 162.0(4) . . . . ?
C9 C8 O2 C17 15.4(4) . . . . ?
C9 C10 C11 C12 -174.2(4) . . . . ?
C9 C10 C11 N1 4.8(5) . . . . ?
C9 C10 C15 C14 174.6(4) . . . . ?
C9 C16 C17 C18 175.0(4) . . . . ?
C9 C16 C17 O2 -4.3(5) . . . . ?
C9 C16 C21 C20 -175.3(4) . . . . ?
C9 C16 C21 C22 4.1(8) . . . . ?
C10 C9 C16 C17 -92.5(4) . . . . ?
C10 C9 C16 C21 84.5(5) . . . . ?
C10 C9 N3 C26 53.7(6) . . . . ?
C10 C11 C12 C13 -1.5(7) . . . . ?
C10 C11 N1 C7 160.9(4) . . . . ?
C10 C11 N1 C8 -15.7(5) . . . . ?
C11 C10 C15 C14 -1.5(7) . . . . ?
C11 C12 C13 C14 -0.5(8) . . . . ?
C12 C11 N1 C7 -20.2(8) . . . . ?
C12 C11 N1 C8 163.2(5) . . . . ?
C12 C13 C14 C15 1.5(8) . . . . ?
C13 C14 C15 C10 -0.5(8) . . . . ?
C15 C10 C11 C12 2.5(7) . . . . ?
C15 C10 C11 N1 -178.4(4) . . . . ?
C16 C9 C10 C11 113.4(4) . . . . ?
C16 C9 C10 C15 -63.1(6) . . . . ?
C16 C9 N3 C26 -177.6(4) . . . . ?
C16 C17 C18 C19 1.7(8) . . . . ?
C16 C17 O2 C8 -7.6(5) . . . . ?
C16 C21 C22 C23 178.1(5) . . . . ?
C17 C16 C21 C20 1.4(6) . . . . ?
C17 C16 C21 C22 -179.2(5) . . . . ?
C17 C18 C19 C20 -0.1(8) . . . . ?
C18 C17 O2 C8 173.1(4) . . . . ?
C18 C19 C20 C21 -0.8(8) . . . . ?
C18 C19 C20 C25 177.9(6) . . . . ?
C19 C20 C21 C16 0.1(7) . . . . ?
C19 C20 C21 C22 -179.3(5) . . . . ?
C19 C20 C25 C24 -179.0(7) . . . . ?
C20 C21 C22 C23 -2.6(7) . . . . ?
C21 C16 C17 C18 -2.4(7) . . . . ?
C21 C16 C17 O2 178.3(4) . . . . ?
C21 C20 C25 C24 -0.3(9) . . . . ?
C21 C22 C23 C24 1.4(9) . . . . ?
C22 C23 C24 C25 0.4(11) . . . . ?
C23 C24 C25 C20 -0.9(11) . . . . ?
C25 C20 C21 C16 -178.6(5) . . . . ?
C25 C20 C21 C22 2.0(7) . . . . ?
C28 C27 O4 C26 176.7(5) . . . . ?
C29 C27 O4 C26 58.7(7) . . . . ?
C30 C27 O4 C26 -66.7(6) . . . . ?
Cl1 C3 C4 C5 178.7(4) . . . . ?
N1 C8 C9 C10 -15.6(4) . . . . ?
N1 C8 C9 C16 -129.7(4) . . . . ?
N1 C8 C9 N3 109.7(4) . . . . ?
N1 C8 N2 C5 39.5(6) . . . . ?
N1 C8 O2 C17 128.1(4) . . . . ?
N1 C11 C12 C13 179.7(5) . . . . ?
N2 C5 C6 C1 -177.8(5) . . . . ?
N2 C5 C6 C7 -1.7(7) . . . . ?
N2 C8 C9 C10 -141.5(4) . . . . ?
N2 C8 C9 C16 104.4(4) . . . . ?
N2 C8 C9 N3 -16.2(6) . . . . ?
N2 C8 N1 C7 -30.2(6) . . . . ?
N2 C8 N1 C11 146.6(4) . . . . ?
N2 C8 O2 C17 -108.7(4) . . . . ?
N3 C9 C10 C11 -117.7(4) . . . . ?
N3 C9 C10 C15 65.8(6) . . . . ?
N3 C9 C16 C17 136.2(4) . . . . ?
N3 C9 C16 C21 -46.8(6) . . . . ?
N3 C26 O4 C27 -176.0(4) . . . . ?
O1 C7 N1 C8 -176.5(5) . . . . ?
O1 C7 N1 C11 7.3(8) . . . . ?
O2 C8 C9 C10 97.2(3) . . . . ?
O2 C8 C9 C16 -16.9(4) . . . . ?
O2 C8 C9 N3 -137.6(4) . . . . ?
O2 C8 N1 C7 91.5(5) . . . . ?
O2 C8 N1 C11 -91.7(4) . . . . ?
O2 C8 N2 C5 -80.0(5) . . . . ?
O2 C17 C18 C19 -179.1(5) . . . . ?
O3 C26 N3 C9 165.7(4) . . . . ?
O3 C26 O4 C27 3.3(7) . . . . ?
O4 C26 N3 C9 -15.0(6) . . . . ?


_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.889
####################################################################### 
# 
# 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_2101255633_1902_0m
_database_code_depnum_ccdc_archive 'CCDC 2312827'
loop_
_audit_author_name
_audit_author_address
'YONG YOU'
;Chengdu University
China
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H25 N3 O4'
_chemical_formula_sum            'C30 H25 N3 O4'
_chemical_formula_weight         491.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7314(12)
_cell_length_b                   20.881(3)
_cell_length_c                   15.894(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.278(9)
_cell_angle_gamma                90
_cell_volume                     2516.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    392
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      52.062
_cell_measurement_theta_min      8.140
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1231 before and 0.0852 after correction. The Ratio of minimum to maximum transmission is 0.3920. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_unetI/netI     0.1147
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15091
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.591
_diffrn_reflns_theta_min         5.400
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2379
_reflns_number_total             4819
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      0.958
_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)+(0.1079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.2145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.3170(3) 0.80887(12) 0.46722(14) 0.0523(7) Uani 1 1 d . . . . .
O2 O 0.2146(3) 0.71395(11) 0.84121(15) 0.0490(7) Uani 1 1 d . . . . .
H2 H 0.228355 0.745658 0.810658 0.074 Uiso 1 1 calc GR . . . .
O3 O 0.5980(3) 0.85386(11) 0.75870(15) 0.0516(7) Uani 1 1 d . . . . .
O4 O 0.6860(3) 0.83983(12) 0.90342(14) 0.0562(7) Uani 1 1 d . . . . .
N1 N 0.3992(4) 0.77205(13) 0.60490(16) 0.0380(7) Uani 1 1 d . . . . .
N2 N 0.2296(4) 0.79010(13) 0.71119(17) 0.0422(7) Uani 1 1 d . . . . .
N3 N 0.5775(4) 0.75778(14) 0.82189(16) 0.0450(8) Uani 1 1 d . . . . .
H3 H 0.594420 0.736614 0.870690 0.054 Uiso 1 1 calc R . . . .
C1 C 0.5042(5) 0.72432(15) 0.74198(19) 0.0383(8) Uani 1 1 d . . . . .
C2 C 0.6315(5) 0.71589(16) 0.6822(2) 0.0403(8) Uani 1 1 d . . . . .
C3 C 0.7985(5) 0.68796(18) 0.6972(2) 0.0510(10) Uani 1 1 d . . . . .
H3A H 0.848897 0.671444 0.752261 0.061 Uiso 1 1 calc R . . . .
C4 C 0.8896(5) 0.68473(18) 0.6305(2) 0.0549(10) Uani 1 1 d . . . . .
H4 H 1.002810 0.665259 0.639708 0.066 Uiso 1 1 calc R . . . .
C5 C 0.8172(5) 0.70973(18) 0.5499(2) 0.0542(10) Uani 1 1 d . . . . .
H5 H 0.881507 0.706398 0.504947 0.065 Uiso 1 1 calc R . . . .
C6 C 0.6532(5) 0.73935(17) 0.5339(2) 0.0467(9) Uani 1 1 d . . . . .
H6 H 0.604032 0.756853 0.479263 0.056 Uiso 1 1 calc R . . . .
C7 C 0.5649(5) 0.74203(16) 0.6020(2) 0.0397(8) Uani 1 1 d . . . . .
C8 C 0.3630(4) 0.76604(16) 0.6860(2) 0.0376(8) Uani 1 1 d . . . . .
C9 C 0.2890(5) 0.80709(16) 0.5404(2) 0.0412(9) Uani 1 1 d . . . . .
C10 C 0.1457(4) 0.83946(16) 0.5699(2) 0.0426(9) Uani 1 1 d . . . . .
C11 C 0.0374(5) 0.88234(18) 0.5155(2) 0.0542(10) Uani 1 1 d . . . . .
H11 H 0.056698 0.889950 0.459164 0.065 Uiso 1 1 calc R . . . .
C12 C -0.0960(6) 0.9131(2) 0.5441(3) 0.0646(12) Uani 1 1 d . . . . .
H12 H -0.166047 0.943676 0.508342 0.077 Uiso 1 1 calc R . . . .
C13 C -0.1299(5) 0.9002(2) 0.6243(3) 0.0668(12) Uani 1 1 d . . . . .
H13 H -0.226574 0.920634 0.642103 0.080 Uiso 1 1 calc R . . . .
C14 C -0.0258(5) 0.85819(19) 0.6794(3) 0.0553(10) Uani 1 1 d . . . . .
H14 H -0.050063 0.849546 0.734660 0.066 Uiso 1 1 calc R . . . .
C15 C 0.1151(5) 0.82884(16) 0.6524(2) 0.0426(9) Uani 1 1 d . . . . .
C16 C 0.4177(4) 0.66121(16) 0.76435(19) 0.0397(9) Uani 1 1 d . . . . .
C17 C 0.4795(5) 0.60172(17) 0.7382(2) 0.0471(9) Uani 1 1 d . . . . .
H17 H 0.571225 0.601391 0.706196 0.057 Uiso 1 1 calc R . . . .
C18 C 0.4093(5) 0.54522(18) 0.7581(2) 0.0511(10) Uani 1 1 d . . . . .
H18 H 0.454702 0.506179 0.740650 0.061 Uiso 1 1 calc R . . . .
C19 C 0.2717(5) 0.54339(16) 0.8038(2) 0.0442(9) Uani 1 1 d . . . . .
C20 C 0.1953(5) 0.48503(19) 0.8252(3) 0.0579(11) Uani 1 1 d . . . . .
H20 H 0.238606 0.445316 0.808751 0.069 Uiso 1 1 calc R . . . .
C21 C 0.0610(5) 0.4857(2) 0.8689(3) 0.0608(11) Uani 1 1 d . . . . .
H21 H 0.012118 0.446354 0.883086 0.073 Uiso 1 1 calc R . . . .
C22 C -0.0064(5) 0.5435(2) 0.8934(3) 0.0578(11) Uani 1 1 d . . . . .
H22 H -0.101833 0.543044 0.923108 0.069 Uiso 1 1 calc R . . . .
C23 C 0.0645(5) 0.60057(18) 0.8749(2) 0.0472(9) Uani 1 1 d . . . . .
H23 H 0.018664 0.639558 0.892226 0.057 Uiso 1 1 calc R . . . .
C24 C 0.2060(5) 0.60198(16) 0.8299(2) 0.0422(9) Uani 1 1 d . . . . .
C25 C 0.2835(5) 0.66058(16) 0.8104(2) 0.0407(8) Uani 1 1 d . . . . .
C26 C 0.6198(5) 0.82047(18) 0.8222(2) 0.0442(9) Uani 1 1 d . . . . .
C27 C 0.7149(6) 0.90736(18) 0.9243(2) 0.0589(11) Uani 1 1 d . . . . .
C28 C 0.8534(8) 0.9349(3) 0.8796(4) 0.115(2) Uani 1 1 d . . . . .
H28A H 0.958836 0.907774 0.891021 0.173 Uiso 1 1 calc GR . . . .
H28B H 0.884070 0.978247 0.901047 0.173 Uiso 1 1 calc GR . . . .
H28C H 0.807141 0.936533 0.817653 0.173 Uiso 1 1 calc GR . . . .
C29 C 0.5397(7) 0.9428(2) 0.9024(3) 0.1003(19) Uani 1 1 d . . . . .
H29A H 0.497831 0.942605 0.840060 0.150 Uiso 1 1 calc GR . . . .
H29B H 0.555780 0.987082 0.922768 0.150 Uiso 1 1 calc GR . . . .
H29C H 0.452826 0.921467 0.930148 0.150 Uiso 1 1 calc GR . . . .
C30 C 0.7818(7) 0.9061(2) 1.0205(3) 0.0782(14) Uani 1 1 d . . . . .
H30A H 0.700154 0.881373 1.047842 0.117 Uiso 1 1 calc GR . . . .
H30B H 0.789820 0.949983 1.042826 0.117 Uiso 1 1 calc GR . . . .
H30C H 0.898725 0.886123 1.033178 0.117 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
O1 C9 1.225(4) . ?
O2 H2 0.8400 . ?
O2 C25 1.367(4) . ?
O3 C26 1.211(4) . ?
O4 C26 1.355(4) . ?
O4 C27 1.456(4) . ?
N1 C7 1.435(4) . ?
N1 C8 1.377(4) . ?
N1 C9 1.403(4) . ?
N2 C8 1.280(4) . ?
N2 C15 1.410(4) . ?
N3 H3 0.8800 . ?
N3 C1 1.463(4) . ?
N3 C26 1.349(4) . ?
C1 C2 1.506(5) . ?
C1 C8 1.537(5) . ?
C1 C16 1.550(5) . ?
C2 C3 1.394(5) . ?
C2 C7 1.389(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(5) . ?
C9 C10 1.451(5) . ?
C10 C11 1.402(5) . ?
C10 C15 1.396(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(5) . ?
C16 C17 1.422(5) . ?
C16 C25 1.382(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.361(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.401(5) . ?
C19 C20 1.424(5) . ?
C19 C24 1.417(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.357(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.399(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.368(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.420(5) . ?
C24 C25 1.423(5) . ?
C27 C28 1.511(6) . ?
C27 C29 1.522(6) . ?
C27 C30 1.516(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C25 O2 H2 109.5 . . ?
C26 O4 C27 121.3(3) . . ?
C8 N1 C7 109.6(3) . . ?
C8 N1 C9 121.7(3) . . ?
C9 N1 C7 128.5(3) . . ?
C8 N2 C15 117.2(3) . . ?
C1 N3 H3 119.4 . . ?
C26 N3 H3 119.4 . . ?
C26 N3 C1 121.2(3) . . ?
N3 C1 C2 114.4(3) . . ?
N3 C1 C8 110.1(3) . . ?
N3 C1 C16 108.5(2) . . ?
C2 C1 C8 100.3(3) . . ?
C2 C1 C16 114.2(3) . . ?
C8 C1 C16 109.0(3) . . ?
C3 C2 C1 129.7(3) . . ?
C7 C2 C1 111.2(3) . . ?
C7 C2 C3 119.1(3) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 121.8 . . ?
C5 C6 C7 116.4(3) . . ?
C7 C6 H6 121.8 . . ?
C2 C7 N1 108.4(3) . . ?
C6 C7 N1 128.3(3) . . ?
C6 C7 C2 123.3(3) . . ?
N1 C8 C1 110.0(3) . . ?
N2 C8 N1 125.5(3) . . ?
N2 C8 C1 124.4(3) . . ?
O1 C9 N1 121.0(3) . . ?
O1 C9 C10 125.4(3) . . ?
N1 C9 C10 113.6(3) . . ?
C11 C10 C9 120.0(3) . . ?
C15 C10 C9 120.6(3) . . ?
C15 C10 C11 119.3(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(4) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 N2 120.9(3) . . ?
C14 C15 N2 118.5(3) . . ?
C14 C15 C10 120.5(3) . . ?
C17 C16 C1 119.4(3) . . ?
C25 C16 C1 122.1(3) . . ?
C25 C16 C17 118.5(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 122.7(3) . . ?
C18 C19 C24 118.7(3) . . ?
C24 C19 C20 118.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(4) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 119.0(3) . . ?
C19 C24 C25 119.2(3) . . ?
C23 C24 C25 121.7(3) . . ?
O2 C25 C16 124.6(3) . . ?
O2 C25 C24 114.4(3) . . ?
C16 C25 C24 121.0(3) . . ?
O3 C26 O4 126.0(3) . . ?
O3 C26 N3 124.2(3) . . ?
N3 C26 O4 109.8(3) . . ?
O4 C27 C28 110.6(4) . . ?
O4 C27 C29 109.2(4) . . ?
O4 C27 C30 102.7(3) . . ?
C28 C27 C29 112.8(4) . . ?
C28 C27 C30 110.4(4) . . ?
C30 C27 C29 110.7(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
