# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_201908203
_database_code_depnum_ccdc_archive 'CCDC 1950729'
loop_
_audit_author_name
_audit_author_address
'Jing Zhou'
;Chongqing Medical University
China
;
_audit_update_record             
;
2019-09-02 deposited with the CCDC.	2020-03-13 downloaded from the CCDC.
;
_audit_creation_date             2019-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 Cl N O5'
_chemical_formula_sum            'C29 H32 Cl N O5'
_chemical_formula_weight         510.00
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20n4o4Cl1
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'

_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                   9.6244(3)
_cell_length_b                   9.8943(3)
_cell_length_c                   14.3864(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.360(3)
_cell_angle_gamma                90
_cell_volume                     1366.00(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9350
_cell_measurement_theta_min      4.5930
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    1.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83230
_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    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11041
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.608
_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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -16.00   1.00    1.00    --  -33.50 -57.00-180.00   32
  2  ω    -92.00 -66.00   1.00    1.00    --  -33.50 -57.00-180.00   26
  3  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00 -60.00   98
  4  ω     33.00  59.00   1.00    1.00    --   36.47  57.00 120.00   26
  5  ω     16.00  51.00   1.00    1.00    --   36.47  37.00-120.00   35
  6  ω     52.00  78.00   1.00    1.00    --   36.47  77.00-150.00   26
  7  ω     11.00  61.00   1.00    1.00    --   36.47  77.00  60.00   50
  8  ω     43.00  90.00   1.00    1.00    --   36.47  19.00-180.00   47
  9  ω     -2.00  51.00   1.00    1.00    --   36.47 -77.00 150.00   53
 10  ω      3.00  31.00   1.00    1.00    --   36.47  88.00 171.58   28
 11  ω     58.00  95.00   1.00    1.00    --   36.47 178.00-180.00   37
 12  ω     58.00  91.00   1.00    1.00    --   36.47 178.00   0.00   33
 13  ω     21.00  47.00   1.00    1.00    --   36.47  37.00 -60.00   26
 14  ω     58.00  88.00   1.00    1.00    --   36.47 178.00  60.00   30
 15  ω     18.00 105.00   1.00    1.00    --   36.47  57.00  60.00   87
 16  ω     73.00 100.00   1.00    1.00    --   36.47  37.00 -60.00   27
 17  ω     61.00 102.00   1.00    1.00    --   36.47 178.00 120.00   41
 18  ω     16.00  45.00   1.00    1.00    --   36.47  77.00-120.00   29
 19  ω     50.00 103.00   1.00    1.00    --   36.47  77.00-120.00   53
 20  ω     37.00 111.00   1.00    5.00    --  108.00-111.00 -90.00   74
 21  ω    123.00 169.00   1.00    5.00    --  108.00  61.00-150.00   46
 22  ω     38.00  85.00   1.00    5.00    --  108.00 -94.00  60.00   47
 23  ω     82.00 115.00   1.00    5.00    --  108.00  30.00-120.00   33
 24  ω    113.00 176.00   1.00    5.00    --  108.00  77.00 150.00   63
 25  ω     85.00 116.00   1.00    5.00    --  108.00  30.00-180.00   31
 26  ω     88.00 114.00   1.00    5.00    --  108.00  61.00-150.00   26
 27  ω     68.00 175.00   1.00    5.00    --  108.00  15.00 -90.00  107
 28  ω     89.00 115.00   1.00    5.00    --  108.00  61.00 120.00   26
 29  ω     83.00 109.00   1.00    5.00    --  108.00  30.00 150.00   26
 30  ω     88.00 115.00   1.00    5.00    --  108.00  61.00  90.00   27
 31  ω     79.00 105.00   1.00    5.00    --  108.00  77.00 150.00   26
 32  ω    153.00 178.00   1.00    5.00    --  108.00 111.00-120.00   25
 33  ω    134.00 173.00   1.00    5.00    --  108.00 111.00 -60.00   39
 34  ω    112.00 175.00   1.00    5.00    --  108.00  77.00  90.00   63
 35  ω     88.00 114.00   1.00    5.00    --  108.00  45.00  90.00   26
 36  ω     79.00 104.00   1.00    5.00    --  108.00  77.00  90.00   25
 37  ω    118.00 174.00   1.00    5.00    --  108.00  77.00 120.00   56
 38  ω     90.00 126.00   1.00    5.00    --  108.00  61.00-180.00   36
 39  ω     80.00 106.00   1.00    5.00    --  108.00  77.00 120.00   26
 40  ω     56.00 118.00   1.00    5.00    --  108.00 -77.00 -90.00   62
 41  ω     82.00 112.00   1.00    5.00    --  108.00  30.00-150.00   30
 42  ω    147.00 173.00   1.00    5.00    --  108.00  45.00  90.00   26
 43  ω    128.00 155.00   1.00    5.00    --  108.00  77.00-180.00   27
 44  ω     90.00 118.00   1.00    5.00    --  108.00  61.00 150.00   28
 45  ω     79.00 105.00   1.00    5.00    --  108.00  77.00-180.00   26
 46  ω     79.00 105.00   1.00    5.00    --  108.00  77.00-150.00   26
 47  ω    102.00 128.00   1.00    5.00    --  108.00 111.00-120.00   26
 48  ω     87.00 119.00   1.00    5.00    --  108.00  30.00 120.00   32
;
_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      0.0572167000
_diffrn_orient_matrix_UB_12      -0.0633222000
_diffrn_orient_matrix_UB_13      -0.0871894000
_diffrn_orient_matrix_UB_21      -0.1401891000
_diffrn_orient_matrix_UB_22      0.0271477000
_diffrn_orient_matrix_UB_23      -0.0558293000
_diffrn_orient_matrix_UB_31      0.0532150000
_diffrn_orient_matrix_UB_32      0.1396083000
_diffrn_orient_matrix_UB_33      -0.0286930000
_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         0.783
_reflns_Friedel_fraction_full    0.887
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                4182
_reflns_number_total             4633
_reflns_odcompleteness_completeness 99.88
_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         0.162
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1608 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(19)
_refine_ls_extinction_coef       0.0135(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.048
_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)+(0.0813P)²+0.0758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1350
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O5(H5A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C14(H14), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.1782(3) 0.5897(4) 0.8588(2) 0.0480(8) Uani 1 1 d . . . . .
C2 C 0.1637(5) 0.7029(5) 0.9126(3) 0.0635(11) Uani 1 1 d . . . . .
H2 H 0.1828 0.6976 0.9768 0.076 Uiso 1 1 calc R . . . .
C3 C 0.1218(5) 0.8231(5) 0.8730(3) 0.0671(12) Uani 1 1 d . . . . .
H3 H 0.1114 0.8994 0.9096 0.080 Uiso 1 1 calc R . . . .
C4 C 0.0955(4) 0.8286(4) 0.7777(3) 0.0569(9) Uani 1 1 d . . . . .
C5 C 0.1058(4) 0.7152(4) 0.7229(3) 0.0476(8) Uani 1 1 d . . . . .
H5 H 0.0848 0.7212 0.6588 0.057 Uiso 1 1 calc R . . . .
C6 C 0.1470(3) 0.5926(4) 0.7624(2) 0.0410(7) Uani 1 1 d . . . . .
C7 C 0.1613(3) 0.4642(4) 0.7055(2) 0.0404(7) Uani 1 1 d . . . . .
H7 H 0.1254 0.3892 0.7412 0.048 Uiso 1 1 calc R . . . .
C8 C 0.0711(3) 0.4730(4) 0.6133(2) 0.0474(8) Uani 1 1 d . . . . .
H8A H -0.0171 0.5152 0.6242 0.057 Uiso 1 1 calc R . . . .
H8B H 0.1176 0.5293 0.5700 0.057 Uiso 1 1 calc R . . . .
C9 C 0.3141(3) 0.4334(3) 0.6916(2) 0.0400(7) Uani 1 1 d . . . . .
C10 C 0.3952(3) 0.5303(3) 0.6511(2) 0.0403(7) Uani 1 1 d . . . . .
H10 H 0.3536 0.6104 0.6297 0.048 Uiso 1 1 calc R . . . .
C11 C 0.5364(3) 0.5108(3) 0.6416(2) 0.0396(7) Uani 1 1 d . . . . .
C12 C 0.5954(3) 0.3886(4) 0.6763(2) 0.0430(7) Uani 1 1 d . . . . .
C13 C 0.5167(3) 0.2868(4) 0.7150(2) 0.0429(7) Uani 1 1 d . . . . .
C14 C 0.3746(3) 0.3132(3) 0.7216(2) 0.0417(7) Uani 1 1 d . . . . .
H14 H 0.3195 0.2477 0.7470 0.050 Uiso 1 1 calc R . . . .
C15 C 0.6240(4) 0.6200(4) 0.5975(3) 0.0469(8) Uani 1 1 d . . . . .
C16 C 0.5343(4) 0.7413(4) 0.5623(3) 0.0597(10) Uani 1 1 d . . . . .
H16A H 0.4623 0.7107 0.5173 0.089 Uiso 1 1 calc GR . . . .
H16B H 0.5919 0.8061 0.5338 0.089 Uiso 1 1 calc GR . . . .
H16C H 0.4928 0.7826 0.6138 0.089 Uiso 1 1 calc GR . . . .
C17 C 0.6928(4) 0.5618(5) 0.5125(3) 0.0586(10) Uani 1 1 d . . . . .
H17A H 0.7461 0.4831 0.5312 0.088 Uiso 1 1 calc GR . . . .
H17B H 0.7531 0.6286 0.4887 0.088 Uiso 1 1 calc GR . . . .
H17C H 0.6219 0.5376 0.4649 0.088 Uiso 1 1 calc GR . . . .
C18 C 0.7342(4) 0.6763(4) 0.6713(3) 0.0557(9) Uani 1 1 d . . . . .
H18A H 0.6882 0.7222 0.7191 0.083 Uiso 1 1 calc GR . . . .
H18B H 0.7939 0.7386 0.6421 0.083 Uiso 1 1 calc GR . . . .
H18C H 0.7888 0.6032 0.6984 0.083 Uiso 1 1 calc GR . . . .
C19 C 0.5819(4) 0.1531(4) 0.7516(3) 0.0524(9) Uani 1 1 d . . . . .
C20 C 0.6565(5) 0.0778(5) 0.6766(3) 0.0648(11) Uani 1 1 d . . . . .
H20A H 0.5954 0.0705 0.6209 0.097 Uiso 1 1 calc GR . . . .
H20B H 0.6821 -0.0109 0.6987 0.097 Uiso 1 1 calc GR . . . .
H20C H 0.7388 0.1268 0.6632 0.097 Uiso 1 1 calc GR . . . .
C21 C 0.6857(6) 0.1808(5) 0.8376(3) 0.0764(14) Uani 1 1 d . . . . .
H21A H 0.7599 0.2375 0.8195 0.115 Uiso 1 1 calc GR . . . .
H21B H 0.7235 0.0967 0.8612 0.115 Uiso 1 1 calc GR . . . .
H21C H 0.6378 0.2252 0.8851 0.115 Uiso 1 1 calc GR . . . .
C22 C 0.4711(5) 0.0545(5) 0.7832(4) 0.0740(13) Uani 1 1 d . . . . .
H22A H 0.4224 0.0956 0.8317 0.111 Uiso 1 1 calc GR . . . .
H22B H 0.5156 -0.0269 0.8063 0.111 Uiso 1 1 calc GR . . . .
H22C H 0.4062 0.0333 0.7312 0.111 Uiso 1 1 calc GR . . . .
C23 C 0.1591(4) 0.3765(4) 0.9342(3) 0.0520(8) Uani 1 1 d . . . . .
C24 C 0.2443(4) 0.2760(4) 0.9896(2) 0.0492(8) Uani 1 1 d . . . . .
C25 C 0.3825(4) 0.3011(5) 1.0183(3) 0.0622(10) Uani 1 1 d . . . . .
H25 H 0.4255 0.3806 1.0013 0.075 Uiso 1 1 calc R . . . .
C26 C 0.4561(5) 0.2051(6) 1.0731(3) 0.0719(13) Uani 1 1 d . . . . .
H26 H 0.5489 0.2208 1.0929 0.086 Uiso 1 1 calc R . . . .
C27 C 0.3931(5) 0.0872(5) 1.0984(3) 0.0660(11) Uani 1 1 d . . . . .
H27 H 0.4437 0.0237 1.1346 0.079 Uiso 1 1 calc R . . . .
C28 C 0.2568(6) 0.0634(6) 1.0705(4) 0.0729(12) Uani 1 1 d . . . . .
H28 H 0.2140 -0.0159 1.0882 0.087 Uiso 1 1 calc R . . . .
C29 C 0.1818(5) 0.1580(5) 1.0155(3) 0.0656(11) Uani 1 1 d . . . . .
H29 H 0.0890 0.1414 0.9961 0.079 Uiso 1 1 calc R . . . .
Cl1 Cl 0.05030(15) 0.98262(13) 0.72452(11) 0.0882(4) Uani 1 1 d . . . . .
N1 N 0.0446(4) 0.3369(4) 0.5711(3) 0.0652(10) Uani 1 1 d . . . . .
O1 O 0.2398(2) 0.4756(3) 0.90172(17) 0.0544(7) Uani 1 1 d . . . . .
O2 O 0.0359(3) 0.3746(4) 0.9178(3) 0.0828(11) Uani 1 1 d . . . . .
O3 O 0.0092(5) 0.2460(4) 0.6200(4) 0.1002(13) Uani 1 1 d . . . . .
O4 O 0.0514(8) 0.3276(6) 0.4884(3) 0.143(3) Uani 1 1 d . . . . .
O5 O 0.7365(3) 0.3750(3) 0.6708(2) 0.0623(8) Uani 1 1 d . . . . .
H5A H 0.8308 0.3427 0.6943 0.075 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(6) . ?
C1 C6 1.397(5) . ?
C1 O1 1.397(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(7) . ?
C4 C5 1.379(6) . ?
C4 Cl1 1.746(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C6 C7 1.524(5) . ?
C7 H7 0.9800 . ?
C7 C8 1.531(4) . ?
C7 C9 1.530(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 N1 1.491(6) . ?
C9 C10 1.391(5) . ?
C9 C14 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(4) . ?
C11 C12 1.411(5) . ?
C11 C15 1.537(5) . ?
C12 C13 1.401(5) . ?
C12 O5 1.373(4) . ?
C13 C14 1.403(5) . ?
C13 C19 1.540(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.541(5) . ?
C15 C17 1.545(5) . ?
C15 C18 1.547(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.534(6) . ?
C19 C21 1.554(5) . ?
C19 C22 1.540(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.482(5) . ?
C23 O1 1.356(5) . ?
C23 O2 1.192(5) . ?
C24 C25 1.385(6) . ?
C24 C29 1.378(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.376(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.392(7) . ?
C29 H29 0.9300 . ?
N1 O3 1.207(6) . ?
N1 O4 1.200(6) . ?
O5 H5A 0.9965 . ?

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 C6 121.2(4) . . ?
C2 C1 O1 117.9(3) . . ?
C6 C1 O1 120.5(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(4) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 Cl1 119.5(3) . . ?
C5 C4 Cl1 119.1(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 119.7(3) . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C7 123.0(3) . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C8 110.5(3) . . ?
C6 C7 C9 111.3(3) . . ?
C8 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
C9 C7 C8 112.7(3) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N1 C8 C7 111.7(3) . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C10 C9 C7 119.5(3) . . ?
C14 C9 C7 121.2(3) . . ?
C14 C9 C10 119.3(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 117.0(3) . . ?
C10 C11 C15 120.9(3) . . ?
C12 C11 C15 122.0(3) . . ?
C13 C12 C11 122.8(3) . . ?
O5 C12 C11 115.9(3) . . ?
O5 C12 C13 121.3(3) . . ?
C12 C13 C14 116.9(3) . . ?
C12 C13 C19 122.3(3) . . ?
C14 C13 C19 120.7(3) . . ?
C9 C14 C13 122.0(3) . . ?
C9 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C11 C15 C16 111.9(3) . . ?
C11 C15 C17 110.2(3) . . ?
C11 C15 C18 109.8(3) . . ?
C16 C15 C17 107.1(3) . . ?
C16 C15 C18 106.4(3) . . ?
C17 C15 C18 111.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 C21 110.0(3) . . ?
C13 C19 C22 111.9(3) . . ?
C20 C19 C13 112.2(3) . . ?
C20 C19 C21 109.8(3) . . ?
C20 C19 C22 105.8(4) . . ?
C22 C19 C21 107.1(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 C23 C24 111.3(3) . . ?
O2 C23 C24 126.7(4) . . ?
O2 C23 O1 122.1(4) . . ?
C25 C24 C23 121.3(4) . . ?
C29 C24 C23 118.6(4) . . ?
C29 C24 C25 120.1(4) . . ?
C24 C25 H25 120.6 . . ?
C24 C25 C26 118.8(4) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.8(4) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.8(5) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 C28 120.3(4) . . ?
C24 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
O3 N1 C8 118.8(4) . . ?
O4 N1 C8 116.9(5) . . ?
O4 N1 O3 124.1(5) . . ?
C23 O1 C1 120.1(3) . . ?
C12 O5 H5A 153.0 . . ?

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
C5 H5 O4 0.93 2.62 3.473(6) 151.9 2_556
O5 H5A O3 1.00 2.30 3.056(6) 132.0 1_655

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 -0.6(7) . . . . ?
C1 C6 C7 C8 157.7(3) . . . . ?
C1 C6 C7 C9 -76.4(4) . . . . ?
C2 C1 C6 C5 2.2(5) . . . . ?
C2 C1 C6 C7 -178.7(3) . . . . ?
C2 C1 O1 C23 95.7(4) . . . . ?
C2 C3 C4 C5 2.3(7) . . . . ?
C2 C3 C4 Cl1 -176.8(4) . . . . ?
C3 C4 C5 C6 -1.8(6) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 C8 -23.3(4) . . . . ?
C5 C6 C7 C9 102.7(3) . . . . ?
C6 C1 C2 C3 -1.7(7) . . . . ?
C6 C1 O1 C23 -91.4(4) . . . . ?
C6 C7 C8 N1 -161.0(3) . . . . ?
C6 C7 C9 C10 -56.1(4) . . . . ?
C6 C7 C9 C14 121.5(3) . . . . ?
C7 C8 N1 O3 46.6(5) . . . . ?
C7 C8 N1 O4 -138.2(5) . . . . ?
C7 C9 C10 C11 176.3(3) . . . . ?
C7 C9 C14 C13 -175.8(3) . . . . ?
C8 C7 C9 C10 68.6(4) . . . . ?
C8 C7 C9 C14 -113.8(3) . . . . ?
C9 C7 C8 N1 73.8(4) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C9 C10 C11 C15 -179.4(3) . . . . ?
C10 C9 C14 C13 1.8(5) . . . . ?
C10 C11 C12 C13 3.0(5) . . . . ?
C10 C11 C12 O5 -176.5(3) . . . . ?
C10 C11 C15 C16 -3.5(5) . . . . ?
C10 C11 C15 C17 -122.5(3) . . . . ?
C10 C11 C15 C18 114.4(4) . . . . ?
C11 C12 C13 C14 -2.5(5) . . . . ?
C11 C12 C13 C19 179.2(3) . . . . ?
C12 C11 C15 C16 178.2(3) . . . . ?
C12 C11 C15 C17 59.2(4) . . . . ?
C12 C11 C15 C18 -63.9(4) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C12 C13 C19 C20 -56.8(4) . . . . ?
C12 C13 C19 C21 65.7(5) . . . . ?
C12 C13 C19 C22 -175.4(4) . . . . ?
C14 C9 C10 C11 -1.3(5) . . . . ?
C14 C13 C19 C20 125.0(4) . . . . ?
C14 C13 C19 C21 -112.6(4) . . . . ?
C14 C13 C19 C22 6.4(5) . . . . ?
C15 C11 C12 C13 -178.7(3) . . . . ?
C15 C11 C12 O5 1.9(5) . . . . ?
C19 C13 C14 C9 178.3(3) . . . . ?
C23 C24 C25 C26 177.7(4) . . . . ?
C23 C24 C29 C28 -177.5(4) . . . . ?
C24 C23 O1 C1 -171.2(3) . . . . ?
C24 C25 C26 C27 0.1(8) . . . . ?
C25 C24 C29 C28 0.1(7) . . . . ?
C25 C26 C27 C28 -0.5(8) . . . . ?
C26 C27 C28 C29 0.7(8) . . . . ?
C27 C28 C29 C24 -0.5(8) . . . . ?
C29 C24 C25 C26 0.1(7) . . . . ?
Cl1 C4 C5 C6 177.3(3) . . . . ?
O1 C1 C2 C3 171.2(4) . . . . ?
O1 C1 C6 C5 -170.5(3) . . . . ?
O1 C1 C6 C7 8.6(5) . . . . ?
O1 C23 C24 C25 12.4(5) . . . . ?
O1 C23 C24 C29 -170.0(4) . . . . ?
O2 C23 C24 C25 -168.1(5) . . . . ?
O2 C23 C24 C29 9.5(6) . . . . ?
O2 C23 O1 C1 9.3(6) . . . . ?
O5 C12 C13 C14 176.9(3) . . . . ?
O5 C12 C13 C19 -1.4(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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.848
