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

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

data_exp_1488
_audit_block_doi                 10.5517/ccdc.csd.cc27341k
_database_code_depnum_ccdc_archive 'CCDC 2058587'
loop_
_audit_author_name
_audit_author_address
'Ping Lu'
;Fudan University
China
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O5'
_chemical_formula_sum            'C19 H19 N O5'
_chemical_formula_weight         341.35
_chemical_absolute_configuration unk
_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 0.0181 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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.54130(10)
_cell_length_b                   6.83260(10)
_cell_length_c                   38.8317(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1735.55(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22911
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.2310
_cell_measurement_theta_min      4.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            37967
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.555
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  37.00   1.00    1.00    --    0.00  77.00   0.00   66
  2  ω     51.00  82.00   1.00    1.00    --    0.00  38.00 150.00   31
  3  ω     50.00  80.00   1.00    1.00    --    0.00  82.00  90.00   30
  4  ω    -18.00  80.00   1.00    1.00    --    0.00  38.00 -90.00   98
  5  ω    -12.00  47.00   1.00    1.00    --    0.00  82.00  90.00   59
  6  ω     51.00  88.00   1.00    1.00    --    0.00  38.00-180.00   37
  7  ω      9.00  35.00   1.00    1.00    --    0.00  38.00 150.00   26
  8  ω     44.00  70.00   1.00    1.00    --    0.00  57.00  90.00   26
  9  ω    -18.00  33.00   1.00    1.00    --    0.00  38.00-180.00   51
 10  ω    -23.00  15.00   1.00    1.00    --    0.00  19.00  60.00   38
 11  ω     11.00  84.00   1.00    1.00    --    0.00  57.00  30.00   73
 12  ω    -13.00  13.00   1.00    1.00    --    0.00  57.00  90.00   26
 13  ω     75.00 153.00   1.00    1.00    --   95.80  45.00 -60.00   78
 14  ω     66.00  92.00   1.00    1.00    --   95.80  75.00  54.64   26
 15  ω     67.00 118.00   1.00    1.00    --   95.80  71.00 153.28   51
 16  ω    159.00 184.00   1.00    1.00    --   95.80  82.00 129.00   25
 17  ω    113.00 156.00   1.00    1.00    --   95.80  82.00 129.00   43
 18  ω     64.00 132.00   1.00    1.00    --   95.80  79.00 161.26   68
 19  ω    131.00 156.00   1.00    1.00    --   95.80  66.00  38.05   25
 20  ω     75.00 101.00   1.00    1.00    --   95.80  61.00 120.00   26
 21  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 22  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 129.00   25
 23  ω    153.00 180.00   1.00    1.00    --   95.80  61.00 120.00   27
 24  ω      7.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  121
 25  ω     68.00  94.00   1.00    1.00    --   95.80  82.00-180.00   26
 26  ω     67.00  92.00   1.00    1.00    --   95.80  82.00 -90.00   25
 27  ω     64.00  94.00   1.00    1.00    --   95.80  82.00-120.00   30
 28  ω     73.00  99.00   1.00    1.00    --   95.80  61.00-120.00   26
 29  ω    134.00 168.00   1.00    1.00    --   95.80  61.00-120.00   34
 30  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 31  ω    117.00 143.00   1.00    1.00    --   95.80  77.00 -60.00   26
 32  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 33  ω     65.00 181.00   1.00    1.00    --   95.80  77.00  -9.43  116
 34  ω    133.00 159.00   1.00    1.00    --   95.80  71.00-149.61   26
 35  ω     63.00  95.00   1.00    1.00    --   95.80  82.00  60.00   32
 36  ω     45.00 123.00   1.00    1.00    --   95.80 -82.00  30.00   78
 37  ω     43.00 103.00   1.00    1.00    --   95.80 -82.00 -60.00   60
 38  ω     15.00  41.00   1.00    1.00    --   95.80 -82.00  30.00   26
 39  ω    117.00 144.00   1.00    1.00    --   95.80  82.00  60.00   27
 40  ω     71.00 102.00   1.00    1.00    --   95.80  61.00-150.00   31
 41  ω     66.00  92.00   1.00    1.00    --   95.80  77.00-150.00   26
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 43  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 44  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 45  ω    113.00 185.00   1.00    1.00    --   95.80  82.00 -30.00   72
 46  ω     65.00  99.00   1.00    1.00    --   95.80  77.00  90.00   34
 47  ω    114.00 181.00   1.00    1.00    --   95.80  45.00 -90.00   67
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 49  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 50  ω    116.00 174.00   1.00    1.00    --   95.80  74.00  83.40   58
 51  ω     44.00 127.00   1.00    1.00    --   95.80 -82.00-120.00   83
 52  ω    130.00 155.00   1.00    1.00    --   95.80  45.00 -30.00   25
 53  ω    109.00 182.00   1.00    1.00    --   95.80  82.00-180.00   73
 54  ω     63.00  90.00   1.00    1.00    --   95.80  82.00-150.00   27
 55  ω     75.00 184.00   1.00    1.00    --   95.80  45.00-150.00  109
 56  ω     78.00 166.00   1.00    1.00    --   95.80  45.00 150.00   88
 57  ω     71.00 105.00   1.00    1.00    --   95.80  61.00 -30.00   34
 58  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 59  ω    107.00 184.00   1.00    1.00    --   95.80  77.00  30.00   77
 60  ω     71.00 180.00   1.00    1.00    --   95.80  61.00  60.00  109
 61  ω     62.00 117.00   1.00    1.00    --   95.80 -61.00  30.00   55
 62  ω     75.00 108.00   1.00    1.00    --   95.80  45.00 -90.00   33
 63  ω     75.00 101.00   1.00    1.00    --   95.80  45.00 -30.00   26
 64  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 65  ω     73.00  98.00   1.00    1.00    --   95.80 -82.00 120.00   25
 66  ω     66.00  92.00   1.00    1.00    --   95.80  74.00  83.40   26
 67  ω     68.00  94.00   1.00    1.00    --   95.80  71.00-149.61   26
 68  ω     69.00  95.00   1.00    1.00    --   95.80  66.00  38.05   26
 69  ω     71.00  97.00   1.00    1.00    --   95.80  59.00 -12.51   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359993000
_diffrn_orient_matrix_UB_12      0.2105099000
_diffrn_orient_matrix_UB_13      0.0128707000
_diffrn_orient_matrix_UB_21      0.0321992000
_diffrn_orient_matrix_UB_22      -0.0777313000
_diffrn_orient_matrix_UB_23      0.0368466000
_diffrn_orient_matrix_UB_31      0.2304739000
_diffrn_orient_matrix_UB_32      -0.0219861000
_diffrn_orient_matrix_UB_33      -0.0071384000
_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         0.677
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3069
_reflns_number_total             3095
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.102
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_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     230
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+0.3626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0628
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C15(H15), C19(H19), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
O2 O 0.40121(17) 0.73509(16) 0.60126(3) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.69685(18) 0.70385(18) 0.57195(3) 0.0285(3) Uani 1 1 d . . . . .
O5 O -0.14227(18) 0.40571(17) 0.46298(3) 0.0286(3) Uani 1 1 d . . . . .
O4 O 0.1368(2) 0.30674(18) 0.43803(3) 0.0311(3) Uani 1 1 d . . . . .
O1 O 0.1220(2) 1.15257(17) 0.64814(3) 0.0332(3) Uani 1 1 d . . . . .
N1 N 0.0445(2) 0.38378(18) 0.46208(3) 0.0233(3) Uani 1 1 d . . . . .
C17 C 0.1646(3) 0.4560(2) 0.49143(4) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.5137(2) 0.6840(2) 0.57389(4) 0.0217(3) Uani 1 1 d . . . . .
C16 C 0.0667(3) 0.4856(2) 0.52267(4) 0.0217(3) Uani 1 1 d . . . . .
H16 H -0.071274 0.456265 0.525294 0.026 Uiso 1 1 calc R . . . .
C18 C 0.3692(3) 0.4977(2) 0.48626(4) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.430646 0.476115 0.465003 0.027 Uiso 1 1 calc R . . . .
C6 C 0.3828(3) 0.8986(2) 0.65867(4) 0.0235(3) Uani 1 1 d . . . . .
C15 C 0.1796(3) 0.5599(2) 0.54984(4) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.117538 0.580823 0.571071 0.026 Uiso 1 1 calc R . . . .
C5 C 0.2369(3) 1.0338(2) 0.66873(4) 0.0265(4) Uani 1 1 d . . . . .
C14 C 0.3852(3) 0.6032(2) 0.54545(4) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.4847(3) 0.7835(3) 0.68267(4) 0.0279(4) Uani 1 1 d . . . . .
C19 C 0.4794(3) 0.5722(2) 0.51353(4) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.617078 0.602120 0.510707 0.026 Uiso 1 1 calc R . . . .
C7 C 0.5142(3) 0.8237(2) 0.62942(4) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.611003 0.922937 0.621299 0.030 Uiso 1 1 calc R . . . .
C8 C 0.6159(3) 0.6775(3) 0.65601(4) 0.0292(4) Uani 1 1 d . . . . .
C4 C 0.1959(3) 1.0487(3) 0.70433(4) 0.0320(4) Uani 1 1 d . . . . .
C2 C 0.4495(3) 0.7962(3) 0.71759(4) 0.0351(4) Uani 1 1 d . . . . .
H2 H 0.519822 0.719784 0.733484 0.042 Uiso 1 1 calc R . . . .
C12 C 0.1518(3) 1.1317(3) 0.61180(4) 0.0364(5) Uani 1 1 d . . . . .
H12A H 0.058331 1.215741 0.599772 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.127447 0.998261 0.605243 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.289604 1.167149 0.606012 0.055 Uiso 1 1 calc GR . . . .
C3 C 0.3017(3) 0.9310(3) 0.72739(4) 0.0351(4) Uani 1 1 d . . . . .
H3 H 0.271887 0.943186 0.750712 0.042 Uiso 1 1 calc R . . . .
C9 C 0.5568(3) 0.4644(3) 0.65064(5) 0.0379(4) Uani 1 1 d . . . . .
H9A H 0.600300 0.388538 0.670123 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.621788 0.415595 0.630197 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.411156 0.454390 0.648205 0.057 Uiso 1 1 calc GR . . . .
C10 C 0.8457(3) 0.7047(3) 0.65987(5) 0.0439(5) Uani 1 1 d . . . . .
H10A H 0.876191 0.841515 0.662160 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.913623 0.653512 0.639894 0.066 Uiso 1 1 calc GR . . . .
H10C H 0.892140 0.636224 0.679987 0.066 Uiso 1 1 calc GR . . . .
C11 C 0.0375(4) 1.1908(3) 0.71669(5) 0.0491(5) Uani 1 1 d . . . . .
H11A H 0.074407 1.320696 0.709628 0.074 Uiso 1 1 calc GR . . . .
H11B H 0.029349 1.185509 0.741352 0.074 Uiso 1 1 calc GR . . . .
H11C H -0.092862 1.157069 0.706987 0.074 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
O2 C13 1.3388(19) . ?
O2 C7 1.4522(18) . ?
O3 C13 1.208(2) . ?
O5 N1 1.2315(18) . ?
O4 N1 1.2301(17) . ?
O1 C5 1.365(2) . ?
O1 C12 1.432(2) . ?
N1 C17 1.470(2) . ?
C17 C16 1.387(2) . ?
C17 C18 1.383(2) . ?
C13 C14 1.493(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(2) . ?
C6 C5 1.384(2) . ?
C6 C1 1.390(2) . ?
C6 C7 1.513(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(2) . ?
C5 C4 1.412(2) . ?
C14 C19 1.400(2) . ?
C1 C8 1.527(2) . ?
C1 C2 1.378(2) . ?
C19 H19 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.583(2) . ?
C8 C9 1.521(3) . ?
C8 C10 1.522(3) . ?
C4 C3 1.388(3) . ?
C4 C11 1.499(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C3 H3 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C13 O2 C7 115.28(12) . . ?
C5 O1 C12 116.32(14) . . ?
O5 N1 C17 117.86(13) . . ?
O4 N1 O5 124.09(14) . . ?
O4 N1 C17 118.04(14) . . ?
C16 C17 N1 118.71(14) . . ?
C18 C17 N1 118.29(14) . . ?
C18 C17 C16 122.96(14) . . ?
O2 C13 C14 111.98(13) . . ?
O3 C13 O2 124.41(15) . . ?
O3 C13 C14 123.59(15) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 C17 118.27(15) . . ?
C15 C16 H16 120.9 . . ?
C17 C18 H18 121.0 . . ?
C19 C18 C17 118.08(14) . . ?
C19 C18 H18 121.0 . . ?
C5 C6 C1 121.26(14) . . ?
C5 C6 C7 145.98(15) . . ?
C1 C6 C7 92.26(14) . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.10(14) . . ?
C14 C15 H15 119.9 . . ?
O1 C5 C6 127.66(15) . . ?
O1 C5 C4 115.23(15) . . ?
C6 C5 C4 117.09(15) . . ?
C15 C14 C13 122.21(13) . . ?
C15 C14 C19 120.19(14) . . ?
C19 C14 C13 117.59(14) . . ?
C6 C1 C8 94.78(13) . . ?
C2 C1 C6 122.97(17) . . ?
C2 C1 C8 142.23(17) . . ?
C18 C19 C14 120.39(15) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O2 C7 C6 114.65(13) . . ?
O2 C7 H7 112.0 . . ?
O2 C7 C8 116.22(13) . . ?
C6 C7 H7 112.0 . . ?
C6 C7 C8 87.86(12) . . ?
C8 C7 H7 112.0 . . ?
C1 C8 C7 84.64(13) . . ?
C9 C8 C1 113.86(16) . . ?
C9 C8 C7 114.08(14) . . ?
C9 C8 C10 112.40(17) . . ?
C10 C8 C1 115.49(15) . . ?
C10 C8 C7 113.71(16) . . ?
C5 C4 C11 119.43(17) . . ?
C3 C4 C5 119.69(17) . . ?
C3 C4 C11 120.88(16) . . ?
C1 C2 H2 122.3 . . ?
C1 C2 C3 115.31(17) . . ?
C3 C2 H2 122.3 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C3 C2 123.68(16) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_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 2.690
_oxdiff_exptl_absorpt_empirical_full_min 0.595
####################################################################### 
# 
# 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_cu_d8v20345_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2737g2
_database_code_depnum_ccdc_archive 'CCDC 2058693'
loop_
_audit_author_name
_audit_author_address
'Ping Lu'
;Fudan University
China
;
_audit_update_record             
;
2021-01-26 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5336(2)
_cell_length_b                   7.0040(2)
_cell_length_c                   25.2509(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1155.51(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    8437
_cell_measurement_theta_min      10.51
_cell_measurement_theta_max      140.254

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.619
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4941
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8786
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         7.014
_diffrn_reflns_theta_max         67.471
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2031
_reflns_number_gt                2004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.970

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.4984(2) 0.4988(2) 0.51437(5) 0.0367(4) Uani 1 1 d . . . . .
H1 H 0.5745 0.4263 0.5321 0.055 Uiso 1 1 calc R U . . .
O2 O 0.2938(2) 0.2503(2) 0.45078(6) 0.0427(4) Uani 1 1 d . . . . .
H2 H 0.3331 0.2862 0.4808 0.064 Uiso 1 1 calc R U . . .
C1 C 0.5537(3) 0.4645(2) 0.41402(6) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.6040(3) 0.5603(2) 0.46802(7) 0.0283(4) Uani 1 1 d . . . . .
H2A H 0.7551 0.5585 0.4743 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5393(3) 0.7536(3) 0.44549(7) 0.0313(4) Uani 1 1 d . . . . .
H3A H 0.6324 0.8598 0.4549 0.038 Uiso 1 1 calc R U . . .
H3B H 0.3949 0.7874 0.4528 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5757(3) 0.6711(2) 0.38897(6) 0.0255(4) Uani 1 1 d . . . . .
C5 C 0.4282(3) 0.7263(2) 0.34547(7) 0.0263(4) Uani 1 1 d . . . . .
C6 C 0.3200(3) 0.8970(3) 0.34761(7) 0.0321(4) Uani 1 1 d . . . . .
H6 H 0.3325 0.9770 0.3778 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1937(3) 0.9518(3) 0.30600(8) 0.0395(5) Uani 1 1 d . . . . .
H7 H 0.1222 1.0697 0.3078 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1716(3) 0.8359(3) 0.26209(8) 0.0408(5) Uani 1 1 d . . . . .
H8 H 0.0837 0.8726 0.2339 0.049 Uiso 1 1 calc R U . . .
C9 C 0.2783(3) 0.6665(3) 0.25958(8) 0.0402(5) Uani 1 1 d . . . . .
H9 H 0.2637 0.5863 0.2295 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4069(3) 0.6119(3) 0.30054(7) 0.0348(5) Uani 1 1 d . . . . .
H10 H 0.4812 0.4957 0.2980 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7938(3) 0.7146(3) 0.37030(9) 0.0373(5) Uani 1 1 d . . . . .
H11A H 0.8255 0.6367 0.3391 0.056 Uiso 1 1 calc R U . . .
H11B H 0.8908 0.6847 0.3987 0.056 Uiso 1 1 calc R U . . .
H11C H 0.8048 0.8501 0.3611 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6951(3) 0.3049(3) 0.39601(8) 0.0351(5) Uani 1 1 d . . . . .
H12A H 0.6608 0.2685 0.3596 0.053 Uiso 1 1 calc R U . . .
H12B H 0.6783 0.1943 0.4194 0.053 Uiso 1 1 calc R U . . .
H12C H 0.8373 0.3490 0.3974 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3298(3) 0.3993(3) 0.41298(7) 0.0316(4) Uani 1 1 d . . . . .
H13A H 0.2398 0.5092 0.4210 0.038 Uiso 1 1 calc R U . . .
H13B H 0.2953 0.3526 0.3771 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.425(2) . ?
O1 H1 0.8400 . ?
O2 C13 1.434(2) . ?
O2 H2 0.8400 . ?
C1 C12 1.520(2) . ?
C1 C13 1.532(2) . ?
C1 C2 1.555(2) . ?
C1 C4 1.586(2) . ?
C2 C3 1.529(2) . ?
C2 H2A 1.0000 . ?
C3 C4 1.558(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.512(2) . ?
C4 C11 1.532(2) . ?
C5 C6 1.389(3) . ?
C5 C10 1.396(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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 O1 H1 109.5 . . ?
C13 O2 H2 109.5 . . ?
C12 C1 C13 110.84(15) . . ?
C12 C1 C2 116.84(15) . . ?
C13 C1 C2 110.21(14) . . ?
C12 C1 C4 119.79(14) . . ?
C13 C1 C4 110.57(14) . . ?
C2 C1 C4 86.38(12) . . ?
O1 C2 C3 116.06(15) . . ?
O1 C2 C1 119.16(14) . . ?
C3 C2 C1 89.85(12) . . ?
O1 C2 H2A 110.1 . . ?
C3 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C2 C3 C4 88.29(13) . . ?
C2 C3 H3A 113.9 . . ?
C4 C3 H3A 113.9 . . ?
C2 C3 H3B 113.9 . . ?
C4 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?
C5 C4 C11 108.58(14) . . ?
C5 C4 C3 118.26(15) . . ?
C11 C4 C3 110.50(15) . . ?
C5 C4 C1 117.76(14) . . ?
C11 C4 C1 112.85(14) . . ?
C3 C4 C1 87.67(12) . . ?
C6 C5 C10 118.34(17) . . ?
C6 C5 C4 121.07(15) . . ?
C10 C5 C4 120.47(16) . . ?
C5 C6 C7 120.67(18) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.42(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.34(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.66(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.56(19) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C1 111.24(15) . . ?
O2 C13 H13A 109.4 . . ?
C1 C13 H13A 109.4 . . ?
O2 C13 H13B 109.4 . . ?
C1 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?

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
C12 C1 C2 O1 -97.22(19) . . . . ?
C13 C1 C2 O1 30.5(2) . . . . ?
C4 C1 C2 O1 141.05(15) . . . . ?
C12 C1 C2 C3 142.67(16) . . . . ?
C13 C1 C2 C3 -89.66(15) . . . . ?
C4 C1 C2 C3 20.94(13) . . . . ?
O1 C2 C3 C4 -144.06(15) . . . . ?
C1 C2 C3 C4 -21.30(13) . . . . ?
C2 C3 C4 C5 141.37(15) . . . . ?
C2 C3 C4 C11 -92.68(15) . . . . ?
C2 C3 C4 C1 20.88(13) . . . . ?
C12 C1 C4 C5 99.51(19) . . . . ?
C13 C1 C4 C5 -31.2(2) . . . . ?
C2 C1 C4 C5 -141.48(15) . . . . ?
C12 C1 C4 C11 -28.3(2) . . . . ?
C13 C1 C4 C11 -159.01(16) . . . . ?
C2 C1 C4 C11 90.75(15) . . . . ?
C12 C1 C4 C3 -139.56(16) . . . . ?
C13 C1 C4 C3 89.69(16) . . . . ?
C2 C1 C4 C3 -20.55(13) . . . . ?
C11 C4 C5 C6 -100.63(18) . . . . ?
C3 C4 C5 C6 26.2(2) . . . . ?
C1 C4 C5 C6 129.59(17) . . . . ?
C11 C4 C5 C10 75.5(2) . . . . ?
C3 C4 C5 C10 -157.67(17) . . . . ?
C1 C4 C5 C10 -54.3(2) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C4 C5 C6 C7 176.25(17) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C6 C5 C10 C9 -1.0(3) . . . . ?
C4 C5 C10 C9 -177.21(17) . . . . ?
C12 C1 C13 O2 65.2(2) . . . . ?
C2 C1 C13 O2 -65.68(18) . . . . ?
C4 C1 C13 O2 -159.48(14) . . . . ?

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
O2 H2 O1 0.84 2.02 2.719(2) 139.6 .
O1 H1 O2 0.84 1.94 2.7464(18) 160.2 4_556

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cu_cj_12_94_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc27340j
_database_code_depnum_ccdc_archive 'CCDC 2058586'
loop_
_audit_author_name
_audit_author_address
'Ping Lu'
;Fudan University
China
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-09-20
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_chemical_absolute_configuration ad
_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 0.0181 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      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                   7.4401(3)
_cell_length_b                   6.6742(3)
_cell_length_c                   15.2681(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.3710(10)
_cell_angle_gamma                90
_cell_volume                     753.48(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      5.83
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            51488
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.022
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         5.832
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2620
_reflns_number_total             2643
_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 V8.38A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1178 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2643
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.096
_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)+(0.0382P)²+0.0993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0710
_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.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C17(H17A,H17B,H17C)
;
_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 0.22804(15) 0.5695(2) 0.70641(7) 0.0325(3) Uani 1 1 d . . . . .
O2 O -0.02366(16) 0.5674(2) 0.61016(8) 0.0415(4) Uani 1 1 d . . . . .
O3 O 0.75939(16) 0.4997(2) 0.36893(9) 0.0432(3) Uani 1 1 d . . . . .
O4 O 0.52207(19) 0.5046(3) 0.27424(8) 0.0571(5) Uani 1 1 d . . . . .
N1 N 0.5954(2) 0.5047(2) 0.35004(9) 0.0350(3) Uani 1 1 d . . . . .
C1 C 0.2628(2) 0.5291(3) 0.55570(10) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.4505(2) 0.5260(3) 0.57518(10) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.5026 0.5302 0.6348 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2191(3) 0.6464(3) 0.86437(11) 0.0329(4) Uani 1 1 d . . . . .
C4 C 0.5615(2) 0.5168(3) 0.50818(11) 0.0290(3) Uani 1 1 d . . . . .
H4 H 0.6894 0.5153 0.5207 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1247(2) 0.4731(3) 0.99088(12) 0.0343(4) Uani 1 1 d . . . . .
H5 H 0.0465 0.3838 1.0168 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1069(2) 0.5129(3) 0.90127(11) 0.0307(4) Uani 1 1 d . . . . .
C7 C 0.4795(2) 0.5100(3) 0.42227(10) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.0360(3) 0.2496(3) 0.78235(14) 0.0447(5) Uani 1 1 d . . . . .
H8A H 0.1668 0.2264 0.7883 0.067 Uiso 1 1 calc R U . . .
H8B H -0.0130 0.2348 0.7204 0.067 Uiso 1 1 calc R U . . .
H8C H -0.0215 0.1519 0.8182 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1387(2) 0.5549(3) 0.62524(11) 0.0314(4) Uani 1 1 d . . . . .
C10 C -0.0017(2) 0.4605(3) 0.81353(11) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.2945(2) 0.5077(3) 0.40120(11) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.2431 0.4994 0.3415 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1172(2) 0.6276(3) 0.77402(11) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.0450 0.7507 0.7571 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1854(2) 0.5176(3) 0.46842(11) 0.0342(4) Uani 1 1 d . . . . .
H13 H 0.0576 0.5166 0.4553 0.041 Uiso 1 1 calc R U . . .
C14 C 0.2655(2) 0.5733(3) 1.04020(11) 0.0370(4) Uani 1 1 d . . . . .
H14 H 0.2845 0.5501 1.1019 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3795(3) 0.7060(3) 1.00295(13) 0.0414(5) Uani 1 1 d . . . . .
H15 H 0.4742 0.7695 1.0396 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3578(3) 0.7479(3) 0.91286(13) 0.0408(5) Uani 1 1 d . . . . .
H16 H 0.4333 0.8399 0.8867 0.049 Uiso 1 1 calc R U . . .
C17 C -0.2027(2) 0.5100(5) 0.80497(14) 0.0513(6) Uani 1 1 d . . . . .
H17A H -0.2635 0.4223 0.8439 0.077 Uiso 1 1 calc R U . . .
H17B H -0.2550 0.4895 0.7438 0.077 Uiso 1 1 calc R U . . .
H17C H -0.2190 0.6501 0.8216 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3432(19) . ?
O1 C12 1.444(2) . ?
O2 C9 1.207(2) . ?
O3 N1 1.2227(19) . ?
O4 N1 1.2234(19) . ?
N1 C7 1.474(2) . ?
C1 C2 1.395(2) . ?
C1 C9 1.493(2) . ?
C1 C13 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C4 1.385(2) . ?
C3 C6 1.383(3) . ?
C3 C12 1.504(2) . ?
C3 C16 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C7 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C5 C14 1.391(3) . ?
C6 C10 1.526(2) . ?
C7 C11 1.378(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C10 1.522(3) . ?
C10 C12 1.584(3) . ?
C10 C17 1.523(3) . ?
C11 H11 0.9500 . ?
C11 C13 1.379(2) . ?
C12 H12 1.0000 . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C9 O1 C12 114.56(13) . . ?
O3 N1 O4 123.49(15) . . ?
O3 N1 C7 118.40(14) . . ?
O4 N1 C7 118.11(14) . . ?
C2 C1 C9 122.26(14) . . ?
C13 C1 C2 120.04(15) . . ?
C13 C1 C9 117.63(14) . . ?
C1 C2 H2 119.7 . . ?
C4 C2 C1 120.51(14) . . ?
C4 C2 H2 119.7 . . ?
C6 C3 C12 93.14(15) . . ?
C16 C3 C6 123.18(17) . . ?
C16 C3 C12 143.53(18) . . ?
C2 C4 H4 121.2 . . ?
C7 C4 C2 117.70(14) . . ?
C7 C4 H4 121.2 . . ?
C6 C5 H5 122.4 . . ?
C6 C5 C14 115.23(17) . . ?
C14 C5 H5 122.4 . . ?
C3 C6 C5 121.99(17) . . ?
C3 C6 C10 94.29(14) . . ?
C5 C6 C10 143.72(17) . . ?
C4 C7 N1 118.46(14) . . ?
C11 C7 N1 118.51(14) . . ?
C11 C7 C4 123.03(15) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C8 H8A 109.5 . . ?
C10 C8 H8B 109.5 . . ?
C10 C8 H8C 109.5 . . ?
O1 C9 C1 112.50(13) . . ?
O2 C9 O1 123.59(15) . . ?
O2 C9 C1 123.88(15) . . ?
C6 C10 C12 84.78(13) . . ?
C8 C10 C6 112.86(16) . . ?
C8 C10 C12 113.69(15) . . ?
C8 C10 C17 112.79(18) . . ?
C17 C10 C6 116.41(16) . . ?
C17 C10 C12 113.53(17) . . ?
C7 C11 H11 120.6 . . ?
C7 C11 C13 118.74(15) . . ?
C13 C11 H11 120.6 . . ?
O1 C12 C3 114.11(14) . . ?
O1 C12 C10 118.07(15) . . ?
O1 C12 H12 111.7 . . ?
C3 C12 C10 87.43(13) . . ?
C3 C12 H12 111.7 . . ?
C10 C12 H12 111.7 . . ?
C1 C13 H13 120.0 . . ?
C11 C13 C1 119.95(15) . . ?
C11 C13 H13 120.0 . . ?
C5 C14 H14 118.6 . . ?
C15 C14 C5 122.77(17) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.45(18) . . ?
C16 C15 H15 119.3 . . ?
C3 C16 C15 115.36(18) . . ?
C3 C16 H16 122.3 . . ?
C15 C16 H16 122.3 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O3 N1 C7 C4 2.4(2) . . . . ?
O3 N1 C7 C11 -177.50(18) . . . . ?
O4 N1 C7 C4 -177.88(19) . . . . ?
O4 N1 C7 C11 2.2(3) . . . . ?
N1 C7 C11 C13 -178.42(17) . . . . ?
C1 C2 C4 C7 -0.3(3) . . . . ?
C2 C1 C9 O1 -1.4(2) . . . . ?
C2 C1 C9 O2 176.5(2) . . . . ?
C2 C1 C13 C11 -1.5(3) . . . . ?
C2 C4 C7 N1 178.68(16) . . . . ?
C2 C4 C7 C11 -1.4(3) . . . . ?
C3 C6 C10 C8 108.96(17) . . . . ?
C3 C6 C10 C12 -4.58(14) . . . . ?
C3 C6 C10 C17 -118.30(18) . . . . ?
C4 C7 C11 C13 1.6(3) . . . . ?
C5 C6 C10 C8 -70.5(3) . . . . ?
C5 C6 C10 C12 176.0(3) . . . . ?
C5 C6 C10 C17 62.3(3) . . . . ?
C5 C14 C15 C16 0.5(3) . . . . ?
C6 C3 C12 O1 -124.37(16) . . . . ?
C6 C3 C12 C10 -4.63(14) . . . . ?
C6 C3 C16 C15 0.5(3) . . . . ?
C6 C5 C14 C15 0.7(3) . . . . ?
C6 C10 C12 O1 120.28(16) . . . . ?
C6 C10 C12 C3 4.20(13) . . . . ?
C7 C11 C13 C1 -0.2(3) . . . . ?
C8 C10 C12 O1 7.6(2) . . . . ?
C8 C10 C12 C3 -108.50(16) . . . . ?
C9 O1 C12 C3 -179.17(15) . . . . ?
C9 O1 C12 C10 80.27(19) . . . . ?
C9 C1 C2 C4 -175.14(16) . . . . ?
C9 C1 C13 C11 175.53(18) . . . . ?
C12 O1 C9 O2 -7.7(3) . . . . ?
C12 O1 C9 C1 170.21(15) . . . . ?
C12 C3 C6 C5 -175.59(17) . . . . ?
C12 C3 C6 C10 4.81(15) . . . . ?
C12 C3 C16 C15 174.4(2) . . . . ?
C13 C1 C2 C4 1.7(3) . . . . ?
C13 C1 C9 O1 -178.34(18) . . . . ?
C13 C1 C9 O2 -0.5(3) . . . . ?
C14 C5 C6 C3 -1.4(3) . . . . ?
C14 C5 C6 C10 177.9(2) . . . . ?
C14 C15 C16 C3 -1.1(3) . . . . ?
C16 C3 C6 C5 0.8(3) . . . . ?
C16 C3 C6 C10 -178.77(19) . . . . ?
C16 C3 C12 O1 60.7(3) . . . . ?
C16 C3 C12 C10 -179.6(3) . . . . ?
C17 C10 C12 O1 -123.15(18) . . . . ?
C17 C10 C12 C3 120.78(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_1546
_audit_block_doi                 10.5517/ccdc.csd.cc27342l
_database_code_depnum_ccdc_archive 'CCDC 2058588'
loop_
_audit_author_name
_audit_author_address
'Ping Lu'
;Fudan University
China
;
_audit_update_record             
;
2021-01-24 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2020-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 N2 O6 S'
_chemical_formula_sum            'C22 H24 N2 O6 S'
_chemical_formula_weight         444.49
_chemical_absolute_configuration unk
_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 0.0181 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'
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                   12.53540(10)
_cell_length_b                   10.51100(10)
_cell_length_c                   18.55590(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.2200(10)
_cell_angle_gamma                90
_cell_volume                     2419.80(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33479
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0310
_cell_measurement_theta_min      3.5380
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.612
_exptl_absorpt_coefficient_mu    1.510
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56015
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.848
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  29.00   1.00    1.00    --    0.00 -77.00-180.00   53
  2  ω    -71.00 -34.00   1.00    1.00    --    0.00 -57.00 -60.00   37
  3  ω     52.00  81.00   1.00    1.00    --    0.00  38.00 -30.00   29
  4  ω     -5.00  45.00   1.00    1.00    --    0.00  38.00 -30.00   50
  5  ω    -83.00 -34.00   1.00    1.00    --    0.00 -77.00-180.00   49
  6  ω    -73.00 -46.00   1.00    1.00    --    0.00 -19.00   0.00   27
  7  ω    -81.00  23.00   1.00    1.00    --    0.00 -57.00-150.00  104
  8  ω    -31.00  23.00   1.00    1.00    --    0.00 -57.00 -60.00   54
  9  ω    -19.00  20.00   1.00    1.00    --    0.00 -19.00   0.00   39
 10  ω    -88.00  18.00   1.00    1.00    --    0.00 -38.00  90.00  106
 11  ω    -18.00  65.00   1.00    1.00    --    0.00  38.00  90.00   83
 12  ω     96.00 122.00   1.00    1.00    --   95.80  76.00 -30.05   26
 13  ω     64.00  92.00   1.00    1.00    --   95.80  80.00-127.74   28
 14  ω     72.00  98.00   1.00    1.00    --   95.80  61.00 120.00   26
 15  ω     65.00  90.00   1.00    1.00    --   95.80  76.00 -30.05   25
 16  ω    133.00 175.00   1.00    1.00    --   95.80  78.00  53.16   42
 17  ω     69.00 100.00   1.00    1.00    --   95.80  66.00-140.20   31
 18  ω     72.00 185.00   1.00    1.00    --   95.80  55.00-164.45  113
 19  ω     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 20  ω     65.00  91.00   1.00    1.00    --   95.80  78.00  53.16   26
 21  ω     10.00 128.00   1.00    1.00    --   95.80 -82.00   0.00  118
 22  ω     57.00 126.00   1.00    1.00    --   95.80 -82.00-180.00   69
 23  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 150.00   26
 24  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 25  ω     75.00 180.00   1.00    1.00    --   95.80  45.00  30.00  105
 26  ω    140.00 166.00   1.00    1.00    --   95.80  82.00-120.00   26
 27  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 28  ω     63.00  98.00   1.00    1.00    --   95.80  82.00 120.00   35
 29  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 30  ω      7.00 119.00   1.00    1.00    --   95.80 -82.00 150.00  112
 31  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 32  ω    143.00 185.00   1.00    1.00    --   95.80  75.00 -65.29   42
 33  ω    126.00 179.00   1.00    1.00    --   95.80  74.00 -39.08   53
 34  ω     95.00 127.00   1.00    1.00    --   95.80 -82.00  30.00   32
 35  ω     71.00 185.00   1.00    1.00    --   95.80  61.00  90.00  114
 36  ω     53.00  79.00   1.00    1.00    --   95.80 -82.00  30.00   26
 37  ω    103.00 185.00   1.00    1.00    --   95.80  82.00  30.00   82
 38  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 39  ω     75.00 179.00   1.00    1.00    --   95.80  45.00-180.00  104
 40  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 41  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 42  ω    146.00 172.00   1.00    1.00    --   95.80  82.00 150.00   26
 43  ω     66.00  91.00   1.00    1.00    --   95.80  75.00 -65.29   25
 44  ω     73.00 123.00   1.00    1.00    --   95.80  61.00 -60.00   50
 45  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 46  ω    121.00 182.00   1.00    1.00    --   95.80  82.00-150.00   61
 47  ω     76.00 163.00   1.00    1.00    --   95.80  45.00 150.00   87
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 49  ω     91.00 128.00   1.00    1.00    --   95.80 -82.00-150.00   37
 50  ω     71.00  96.00   1.00    1.00    --   95.80  61.00  30.00   25
 51  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 52  ω     63.00  97.00   1.00    1.00    --   95.80  82.00-120.00   34
 53  ω     21.00  74.00   1.00    1.00    --   95.80 -82.00-150.00   53
 54  ω     71.00  97.00   1.00    1.00    --   95.80  61.00   0.00   26
 55  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 56  ω     76.00 175.00   1.00    1.00    --   95.80  45.00 -60.00   99
 57  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 58  ω    148.00 174.00   1.00    1.00    --   95.80  61.00 120.00   26
 59  ω    122.00 179.00   1.00    1.00    --   95.80  80.00-127.74   57
 60  ω     48.00 123.00   1.00    1.00    --   95.80 -82.00 -30.00   75
 61  ω     66.00  91.00   1.00    1.00    --   95.80  74.00 -39.08   25
 62  ω     70.00  96.00   1.00    1.00    --   95.80  64.00  41.79   26
 63  ω     75.00 107.00   1.00    1.00    --   95.80  45.00 -90.00   32
 64  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 65  ω     71.00 112.00   1.00    1.00    --   95.80  61.00 -30.00   41
 66  ω     74.00 184.00   1.00    1.00    --   95.80  53.00  70.10  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1077786000
_diffrn_orient_matrix_UB_12      0.0391991000
_diffrn_orient_matrix_UB_13      0.0242733000
_diffrn_orient_matrix_UB_21      -0.0583111000
_diffrn_orient_matrix_UB_22      -0.0253078000
_diffrn_orient_matrix_UB_23      -0.0774897000
_diffrn_orient_matrix_UB_31      -0.0198192000
_diffrn_orient_matrix_UB_32      -0.1390208000
_diffrn_orient_matrix_UB_33      0.0209672000
_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         0.850
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                8106
_reflns_number_total             8412
_reflns_odcompleteness_completeness 99.98
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.155
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 3580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         8412
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.1725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C11(H11), C9(H9), C31(H31), C12(H12), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C8(H8A,H8B), C13(H13A,H13B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C44(H44), C22(H22), C43(H43), C24(H24), C5(H5), C21(H21), C2(H2),
 C40(H40), C28(H28), C18(H18), C25(H25), C41(H41), C19(H19), C3(H3), C27(H27)
2.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C), C7(H7A,H7B,H7C), C29(H29A,H29B,H29C)
;
_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
S2 S 0.92901(4) 0.25241(5) 0.39306(3) 0.02121(12) Uani 1 1 d . . . . .
S1 S 0.42125(4) 0.24732(5) 0.41955(3) 0.02276(13) Uani 1 1 d . . . . .
O9 O 0.93748(12) 0.46392(16) 0.68619(8) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.47035(12) 0.46364(16) 0.70634(8) 0.0235(3) Uani 1 1 d . . . . .
O7 O 0.88526(13) 0.12666(16) 0.38598(9) 0.0273(4) Uani 1 1 d . . . . .
O8 O 1.04314(11) 0.27075(18) 0.39877(8) 0.0299(4) Uani 1 1 d . . . . .
O1 O 0.37542(13) 0.12197(16) 0.41376(9) 0.0288(4) Uani 1 1 d . . . . .
O10 O 0.98978(13) 0.29414(17) 0.75644(9) 0.0283(4) Uani 1 1 d . . . . .
O2 O 0.53552(12) 0.26326(19) 0.42418(10) 0.0339(4) Uani 1 1 d . . . . .
O4 O 0.53001(13) 0.29172(17) 0.77251(9) 0.0291(4) Uani 1 1 d . . . . .
N3 N 0.89180(13) 0.31314(19) 0.46611(10) 0.0203(4) Uani 1 1 d . . . . .
N1 N 0.38697(14) 0.31053(19) 0.49298(10) 0.0227(4) Uani 1 1 d . . . . .
O11 O 1.08566(19) 0.8816(2) 0.96025(10) 0.0492(5) Uani 1 1 d . . . . .
N4 N 1.09457(19) 0.7687(2) 0.97551(11) 0.0395(6) Uani 1 1 d . . . . .
O6 O 0.85658(18) 0.7018(2) 0.99888(11) 0.0581(7) Uani 1 1 d . . . . .
C38 C 0.97746(17) 0.4070(2) 0.74908(12) 0.0222(5) Uani 1 1 d . . . . .
O12 O 1.1285(2) 0.7297(2) 1.03666(10) 0.0641(7) Uani 1 1 d . . . . .
C30 C 0.77520(16) 0.3050(2) 0.47286(12) 0.0238(5) Uani 1 1 d . . . . .
H30A H 0.752258 0.217188 0.475480 0.029 Uiso 1 1 calc R . . . .
H30B H 0.731514 0.346384 0.432179 0.029 Uiso 1 1 calc R . . . .
C6 C 0.25320(18) 0.3119(2) 0.31585(13) 0.0258(5) Uani 1 1 d . . . . .
H6 H 0.216162 0.244036 0.332815 0.031 Uiso 1 1 calc R . . . .
C33 C 0.91388(17) 0.3829(2) 0.62328(11) 0.0194(4) Uani 1 1 d . . . . .
H33 H 0.975887 0.330713 0.615303 0.023 Uiso 1 1 calc R . . . .
C16 C 0.52874(17) 0.4051(2) 0.76274(12) 0.0231(5) Uani 1 1 d . . . . .
C32 C 0.80790(17) 0.3042(2) 0.61700(12) 0.0221(5) Uani 1 1 d . . . . .
C1 C 0.35997(17) 0.3374(2) 0.34543(12) 0.0229(5) Uani 1 1 d . . . . .
C23 C 0.86799(18) 0.3425(2) 0.31836(12) 0.0252(5) Uani 1 1 d . . . . .
C11 C 0.42469(17) 0.3829(2) 0.64651(12) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.479432 0.325578 0.631944 0.026 Uiso 1 1 calc R . . . .
C10 C 0.31755(18) 0.3104(2) 0.65082(13) 0.0257(5) Uani 1 1 d . . . . .
C39 C 1.00528(18) 0.5029(2) 0.80832(12) 0.0236(5) Uani 1 1 d . . . . .
C44 C 1.0041(2) 0.6316(3) 0.79306(12) 0.0301(5) Uani 1 1 d . . . . .
H44 H 0.983510 0.659542 0.745541 0.036 Uiso 1 1 calc R . . . .
N2 N 0.7918(2) 0.7471(3) 0.95058(12) 0.0529(7) Uani 1 1 d . . . . .
C22 C 0.5813(2) 0.6279(3) 0.80401(13) 0.0324(6) Uani 1 1 d . . . . .
H22 H 0.529878 0.660247 0.767523 0.039 Uiso 1 1 calc R . . . .
C43 C 1.0332(2) 0.7192(2) 0.84785(13) 0.0323(6) Uani 1 1 d . . . . .
H43 H 1.033004 0.805861 0.837846 0.039 Uiso 1 1 calc R . . . .
C36 C 0.8252(2) 0.1614(2) 0.61354(14) 0.0275(5) Uani 1 1 d . . . . .
H36A H 0.871964 0.142952 0.578183 0.041 Uiso 1 1 calc GR . . . .
H36B H 0.757116 0.119895 0.599809 0.041 Uiso 1 1 calc GR . . . .
H36C H 0.857470 0.131141 0.660442 0.041 Uiso 1 1 calc GR . . . .
C42 C 1.0626(2) 0.6745(3) 0.91801(13) 0.0305(5) Uani 1 1 d . . . . .
C24 C 0.9206(2) 0.4496(3) 0.29648(13) 0.0300(5) Uani 1 1 d . . . . .
H24 H 0.987523 0.473070 0.321208 0.036 Uiso 1 1 calc R . . . .
C20 C 0.7222(2) 0.6581(3) 0.90258(13) 0.0367(7) Uani 1 1 d . . . . .
C17 C 0.59395(18) 0.4982(3) 0.81218(12) 0.0254(5) Uani 1 1 d . . . . .
C9 C 0.27125(17) 0.3752(2) 0.57604(13) 0.0266(5) Uani 1 1 d . . . . .
H9 H 0.204076 0.422106 0.577607 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2037(2) 0.3898(3) 0.26072(13) 0.0328(6) Uani 1 1 d . . . . .
H5 H 0.132500 0.373745 0.241138 0.039 Uiso 1 1 calc R . . . .
C31 C 0.76812(17) 0.3745(2) 0.54349(12) 0.0232(5) Uani 1 1 d . . . . .
H31 H 0.700294 0.420762 0.543619 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3278(2) 0.1673(2) 0.65198(15) 0.0319(6) Uani 1 1 d . . . . .
H14A H 0.367714 0.140571 0.614193 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.257271 0.129723 0.644108 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.364854 0.140602 0.698379 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.6447(3) 0.7096(3) 0.84982(14) 0.0425(7) Uani 1 1 d . . . . .
H21 H 0.635704 0.797230 0.845445 0.051 Uiso 1 1 calc R . . . .
C2 C 0.4154(2) 0.4381(2) 0.31912(14) 0.0319(6) Uani 1 1 d . . . . .
H2 H 0.486663 0.454373 0.338633 0.038 Uiso 1 1 calc R . . . .
C8 C 0.27243(17) 0.2998(3) 0.50603(13) 0.0269(5) Uani 1 1 d . . . . .
H8A H 0.252502 0.211747 0.512227 0.032 Uiso 1 1 calc R . . . .
H8B H 0.223735 0.336696 0.466161 0.032 Uiso 1 1 calc R . . . .
C40 C 1.0338(2) 0.4599(3) 0.87968(13) 0.0323(6) Uani 1 1 d . . . . .
H40 H 1.033457 0.373289 0.889934 0.039 Uiso 1 1 calc R . . . .
C15 C 0.25808(19) 0.3597(3) 0.71148(14) 0.0337(6) Uani 1 1 d . . . . .
H15A H 0.298097 0.338096 0.757898 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.187849 0.321600 0.707043 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.250900 0.450487 0.707638 0.050 Uiso 1 1 calc GR . . . .
C13 C 0.42218(19) 0.4420(2) 0.51278(13) 0.0258(5) Uani 1 1 d . . . . .
H13A H 0.393949 0.502283 0.475278 0.031 Uiso 1 1 calc R . . . .
H13B H 0.500132 0.448593 0.521712 0.031 Uiso 1 1 calc R . . . .
C12 C 0.37296(17) 0.4620(2) 0.58214(12) 0.0238(5) Uani 1 1 d . . . . .
H12 H 0.360023 0.551187 0.593630 0.029 Uiso 1 1 calc R . . . .
C37 C 0.73628(18) 0.3381(3) 0.67386(13) 0.0287(5) Uani 1 1 d . . . . .
H37A H 0.769877 0.310064 0.720922 0.043 Uiso 1 1 calc GR . . . .
H37B H 0.667637 0.296969 0.661960 0.043 Uiso 1 1 calc GR . . . .
H37C H 0.726175 0.428577 0.674546 0.043 Uiso 1 1 calc GR . . . .
C28 C 0.7674(2) 0.3087(3) 0.28203(14) 0.0328(6) Uani 1 1 d . . . . .
H28 H 0.731821 0.237690 0.296660 0.039 Uiso 1 1 calc R . . . .
C4 C 0.2569(3) 0.4904(3) 0.23401(14) 0.0393(7) Uani 1 1 d . . . . .
C35 C 0.92820(18) 0.4425(2) 0.49025(12) 0.0226(5) Uani 1 1 d . . . . .
H35A H 0.906211 0.505358 0.452813 0.027 Uiso 1 1 calc R . . . .
H35B H 1.005841 0.445836 0.503590 0.027 Uiso 1 1 calc R . . . .
C18 C 0.6728(2) 0.4493(3) 0.86591(14) 0.0342(6) Uani 1 1 d . . . . .
H18 H 0.681566 0.361750 0.871016 0.041 Uiso 1 1 calc R . . . .
C25 C 0.8727(3) 0.5212(3) 0.23758(14) 0.0397(7) Uani 1 1 d . . . . .
H25 H 0.908273 0.592234 0.222903 0.048 Uiso 1 1 calc R . . . .
C41 C 1.0626(2) 0.5470(3) 0.93521(13) 0.0381(7) Uani 1 1 d . . . . .
H41 H 1.081500 0.519947 0.983047 0.046 Uiso 1 1 calc R . . . .
C34 C 0.87054(17) 0.4620(2) 0.55614(12) 0.0217(5) Uani 1 1 d . . . . .
H34 H 0.855554 0.551095 0.566549 0.026 Uiso 1 1 calc R . . . .
O5 O 0.7824(3) 0.8587(3) 0.93924(17) 0.1212(16) Uani 1 1 d . . . . .
C19 C 0.7379(2) 0.5307(3) 0.91160(13) 0.0371(6) Uani 1 1 d . . . . .
H19 H 0.790888 0.499187 0.947376 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3639(3) 0.5141(3) 0.26364(15) 0.0427(7) Uani 1 1 d . . . . .
H3 H 0.400854 0.581378 0.246028 0.051 Uiso 1 1 calc R . . . .
C26 C 0.7726(3) 0.4880(3) 0.20046(15) 0.0448(7) Uani 1 1 d . . . . .
C27 C 0.7205(3) 0.3815(3) 0.22388(15) 0.0443(7) Uani 1 1 d . . . . .
H27 H 0.652859 0.359105 0.199902 0.053 Uiso 1 1 calc R . . . .
C7 C 0.1990(3) 0.5750(3) 0.17557(16) 0.0615(10) Uani 1 1 d . . . . .
H7A H 0.158296 0.523540 0.138657 0.092 Uiso 1 1 calc GR . . . .
H7B H 0.250616 0.624688 0.154259 0.092 Uiso 1 1 calc GR . . . .
H7C H 0.151045 0.630653 0.196545 0.092 Uiso 1 1 calc GR . . . .
C29 C 0.7207(4) 0.5658(4) 0.13664(18) 0.0709(12) Uani 1 1 d . . . . .
H29A H 0.657848 0.607603 0.149325 0.106 Uiso 1 1 calc GR . . . .
H29B H 0.700159 0.510921 0.095637 0.106 Uiso 1 1 calc GR . . . .
H29C H 0.770884 0.628320 0.124355 0.106 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
S2 O7 1.4298(18) . ?
S2 O8 1.4325(15) . ?
S2 N3 1.6259(18) . ?
S2 C23 1.761(2) . ?
S1 O1 1.4352(18) . ?
S1 O2 1.4325(15) . ?
S1 N1 1.628(2) . ?
S1 C1 1.754(2) . ?
O9 C38 1.343(3) . ?
O9 C33 1.441(3) . ?
O3 C16 1.338(3) . ?
O3 C11 1.449(3) . ?
O10 C38 1.202(3) . ?
O4 C16 1.205(3) . ?
N3 C30 1.487(3) . ?
N3 C35 1.483(3) . ?
N1 C8 1.494(3) . ?
N1 C13 1.481(3) . ?
O11 N4 1.221(3) . ?
N4 O12 1.224(3) . ?
N4 C42 1.469(3) . ?
O6 N2 1.217(3) . ?
C38 C39 1.495(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.514(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.398(3) . ?
C6 C5 1.386(3) . ?
C33 H33 0.9800 . ?
C33 C32 1.556(3) . ?
C33 C34 1.531(3) . ?
C16 C17 1.501(3) . ?
C32 C36 1.519(3) . ?
C32 C31 1.569(3) . ?
C32 C37 1.522(3) . ?
C1 C2 1.393(3) . ?
C23 C24 1.394(3) . ?
C23 C28 1.388(3) . ?
C11 H11 0.9800 . ?
C11 C10 1.557(3) . ?
C11 C12 1.522(3) . ?
C10 C9 1.580(3) . ?
C10 C14 1.509(3) . ?
C10 C15 1.527(3) . ?
C39 C44 1.383(4) . ?
C39 C40 1.396(3) . ?
C44 H44 0.9300 . ?
C44 C43 1.381(3) . ?
N2 C20 1.486(3) . ?
N2 O5 1.195(4) . ?
C22 H22 0.9300 . ?
C22 C17 1.378(4) . ?
C22 C21 1.378(4) . ?
C43 H43 0.9300 . ?
C43 C42 1.383(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C42 C41 1.377(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.391(4) . ?
C20 C21 1.387(4) . ?
C20 C19 1.361(4) . ?
C17 C18 1.397(3) . ?
C9 H9 0.9800 . ?
C9 C8 1.523(3) . ?
C9 C12 1.559(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.380(4) . ?
C31 H31 0.9800 . ?
C31 C34 1.570(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C21 H21 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C40 H40 0.9300 . ?
C40 C41 1.387(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.519(3) . ?
C12 H12 0.9800 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C28 H28 0.9300 . ?
C28 C27 1.384(4) . ?
C4 C3 1.397(5) . ?
C4 C7 1.507(4) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C34 1.521(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.387(4) . ?
C41 H41 0.9300 . ?
C34 H34 0.9800 . ?
C19 H19 0.9300 . ?
C3 H3 0.9300 . ?
C26 C27 1.396(5) . ?
C26 C29 1.508(4) . ?
C27 H27 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 S2 O8 119.80(11) . . ?
O7 S2 N3 106.71(10) . . ?
O7 S2 C23 107.88(10) . . ?
O8 S2 N3 106.74(9) . . ?
O8 S2 C23 107.62(11) . . ?
N3 S2 C23 107.53(10) . . ?
O1 S1 N1 106.66(10) . . ?
O1 S1 C1 108.14(10) . . ?
O2 S1 O1 119.87(11) . . ?
O2 S1 N1 106.46(10) . . ?
O2 S1 C1 107.81(11) . . ?
N1 S1 C1 107.30(10) . . ?
C38 O9 C33 116.68(18) . . ?
C16 O3 C11 116.25(18) . . ?
C30 N3 S2 116.76(14) . . ?
C35 N3 S2 119.95(15) . . ?
C35 N3 C30 106.92(17) . . ?
C8 N1 S1 118.66(14) . . ?
C13 N1 S1 118.92(16) . . ?
C13 N1 C8 106.81(18) . . ?
O11 N4 O12 123.2(2) . . ?
O11 N4 C42 118.7(2) . . ?
O12 N4 C42 118.1(2) . . ?
O9 C38 C39 111.0(2) . . ?
O10 C38 O9 124.3(2) . . ?
O10 C38 C39 124.7(2) . . ?
N3 C30 H30A 111.2 . . ?
N3 C30 H30B 111.2 . . ?
N3 C30 C31 103.01(17) . . ?
H30A C30 H30B 109.1 . . ?
C31 C30 H30A 111.2 . . ?
C31 C30 H30B 111.2 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C1 118.6(2) . . ?
O9 C33 H33 112.2 . . ?
O9 C33 C32 116.71(17) . . ?
O9 C33 C34 110.28(18) . . ?
C32 C33 H33 112.2 . . ?
C34 C33 H33 112.2 . . ?
C34 C33 C32 91.60(16) . . ?
O3 C16 C17 111.6(2) . . ?
O4 C16 O3 124.5(2) . . ?
O4 C16 C17 123.9(2) . . ?
C33 C32 C31 88.65(16) . . ?
C36 C32 C33 113.8(2) . . ?
C36 C32 C31 117.3(2) . . ?
C36 C32 C37 111.3(2) . . ?
C37 C32 C33 113.91(19) . . ?
C37 C32 C31 110.29(18) . . ?
C6 C1 S1 119.44(18) . . ?
C2 C1 S1 120.05(18) . . ?
C2 C1 C6 120.4(2) . . ?
C24 C23 S2 119.55(18) . . ?
C28 C23 S2 120.5(2) . . ?
C28 C23 C24 120.0(2) . . ?
O3 C11 H11 110.9 . . ?
O3 C11 C10 119.79(18) . . ?
O3 C11 C12 111.04(18) . . ?
C10 C11 H11 110.9 . . ?
C12 C11 H11 110.9 . . ?
C12 C11 C10 91.95(17) . . ?
C11 C10 C9 87.41(17) . . ?
C14 C10 C11 114.6(2) . . ?
C14 C10 C9 117.5(2) . . ?
C14 C10 C15 112.2(2) . . ?
C15 C10 C11 112.8(2) . . ?
C15 C10 C9 110.1(2) . . ?
C44 C39 C38 121.0(2) . . ?
C44 C39 C40 120.3(2) . . ?
C40 C39 C38 118.7(2) . . ?
C39 C44 H44 119.8 . . ?
C43 C44 C39 120.5(2) . . ?
C43 C44 H44 119.8 . . ?
O6 N2 C20 117.9(3) . . ?
O5 N2 O6 123.5(3) . . ?
O5 N2 C20 118.6(3) . . ?
C17 C22 H22 119.9 . . ?
C17 C22 C21 120.1(2) . . ?
C21 C22 H22 119.9 . . ?
C44 C43 H43 120.9 . . ?
C44 C43 C42 118.3(2) . . ?
C42 C43 H43 120.9 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C43 C42 N4 117.6(2) . . ?
C41 C42 N4 119.8(2) . . ?
C41 C42 C43 122.6(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 H24 120.1 . . ?
C21 C20 N2 118.0(3) . . ?
C19 C20 N2 118.9(3) . . ?
C19 C20 C21 123.1(2) . . ?
C22 C17 C16 122.2(2) . . ?
C22 C17 C18 120.0(2) . . ?
C18 C17 C16 117.7(2) . . ?
C10 C9 H9 113.6 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 113.6 . . ?
C8 C9 C12 104.99(19) . . ?
C12 C9 C10 89.70(16) . . ?
C12 C9 H9 113.6 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C30 C31 C32 118.4(2) . . ?
C30 C31 H31 113.6 . . ?
C30 C31 C34 105.32(17) . . ?
C32 C31 H31 113.6 . . ?
C32 C31 C34 89.68(16) . . ?
C34 C31 H31 113.6 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C21 C20 118.4(3) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
N1 C8 C9 103.05(17) . . ?
N1 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C39 C40 H40 120.2 . . ?
C41 C40 C39 119.7(2) . . ?
C41 C40 H40 120.2 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C13 H13A 111.5 . . ?
N1 C13 H13B 111.5 . . ?
N1 C13 C12 101.35(18) . . ?
H13A C13 H13B 109.3 . . ?
C12 C13 H13A 111.5 . . ?
C12 C13 H13B 111.5 . . ?
C11 C12 C9 89.40(17) . . ?
C11 C12 H12 114.6 . . ?
C9 C12 H12 114.6 . . ?
C13 C12 C11 114.21(19) . . ?
C13 C12 C9 106.52(19) . . ?
C13 C12 H12 114.6 . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.5(3) . . ?
C27 C28 H28 120.2 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C7 120.2(3) . . ?
C3 C4 C7 121.0(3) . . ?
N3 C35 H35A 111.4 . . ?
N3 C35 H35B 111.4 . . ?
N3 C35 C34 101.86(18) . . ?
H35A C35 H35B 109.3 . . ?
C34 C35 H35A 111.4 . . ?
C34 C35 H35B 111.4 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C42 C41 C40 118.6(2) . . ?
C42 C41 H41 120.7 . . ?
C40 C41 H41 120.7 . . ?
C33 C34 C31 89.49(17) . . ?
C33 C34 H34 114.5 . . ?
C31 C34 H34 114.5 . . ?
C35 C34 C33 115.27(19) . . ?
C35 C34 C31 105.87(18) . . ?
C35 C34 H34 114.5 . . ?
C20 C19 C18 118.0(2) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C25 C26 C27 118.5(3) . . ?
C25 C26 C29 120.8(3) . . ?
C27 C26 C29 120.7(3) . . ?
C28 C27 C26 121.4(3) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 -0.069 1.000 342.3 81.3 ?

_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 2.180
_oxdiff_exptl_absorpt_empirical_full_min 0.585
