# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_hpd462b
_database_code_depnum_ccdc_archive 'CCDC 2127334'
loop_
_audit_author_name
_audit_author_address
'Luca De Angelis'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-01-05 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-01-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'LDA 05-324P'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.5967(2)
_cell_length_b                   12.8747(2)
_cell_length_c                   15.6198(3)
_cell_angle_alpha                72.566(2)
_cell_angle_beta                 69.8110(10)
_cell_angle_gamma                75.6020(10)
_cell_volume                     2238.30(7)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    21804
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.3230
_cell_measurement_theta_min      3.6420
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             948
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 2 -2 0.0243
7 -1 1 0.0601
-1 3 -8 0.0653
1 -3 8 0.0509
-3 -8 -6 0.0019
8 2 5 0.0619
0 8 4 0.0519

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.074
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.3933 1.5775 -2.1134 0.0044 0.0081 1.0000
7.4456 -1.3544 1.3655 -0.0262 -0.0988 -0.9948
-0.8113 2.6163 -8.1868 -0.2267 -0.9445 0.2377
1.3082 -2.6781 8.1847 0.2223 0.9268 -0.3026
-3.3248 -7.8834 -5.9618 0.9722 -0.2339 -0.0089
8.0892 2.4491 4.8429 -0.4767 0.1169 -0.8713
-0.2067 7.7789 4.4045 -0.8730 0.2090 0.4407

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            42637
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.589
_diffrn_reflns_theta_min         3.101
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     83.00 119.00   0.50    0.07    --   46.75  57.00  90.00   72
  2  ω     83.00 119.00   0.50    0.07    --   46.75  57.00 120.00   72
  3  ω     89.00 178.00   0.50    0.28    --  106.69 135.00 125.00  178
  4  ω     95.00 178.00   0.50    0.28    --  106.69 125.00 150.00  166
  5  ω     83.00 119.00   0.50    0.07    --   46.75  57.00   0.00   72
  6  ω     89.00 178.00   0.50    0.28    --  106.69 134.00 -53.00  178
  7  ω    101.00 178.00   0.50    0.28    --  106.69  77.00-180.00  154
  8  ω    101.00 163.00   0.50    0.28    --  106.69  77.00 -60.00  124
  9  ω     91.00 178.00   0.50    0.28    --  106.69  30.00 -90.00  174
 10  ω     71.00 105.00   0.50    0.28    --  106.69 -94.00 -90.00   68
 11  ω     70.00 110.00   0.50    0.28    --  106.69-125.00-180.00   80
 12  ω     39.00 101.00   0.50    0.07    --   46.75-134.00-121.00  124
 13  ω     39.00 118.00   0.50    0.28    --  106.69-134.00-121.00  158
 14  ω     51.00 101.00   0.50    0.28    --  106.69 -94.00 -30.00  100
 15  ω     40.00 101.00   0.50    0.07    --   46.75-135.00  59.00  122
 16  ω     40.00 119.00   0.50    0.28    --  106.69-135.00  59.00  158
 17  ω     70.00  96.00   0.50    0.28    --  106.69-125.00 150.00   52
 18  ω     44.00  71.00   0.50    0.28    --  106.69 -61.00  90.00   54
 19  ω     34.00 106.00   0.50    0.28    --  106.69 -99.00  93.87  144
 20  ω     36.00  64.00   0.50    0.28    --  106.69 -61.00  60.00   56
 21  ω     35.00  65.00   0.50    0.28    --  106.69-125.00 150.00   60
 22  ω    -29.00  30.00   0.50    0.07    --   46.75 -19.00 150.00  118
 23  ω     35.00  69.00   0.50    0.28    --  106.69 -61.00 -30.00   68
 24  ω     34.00  71.00   0.50    0.28    --  106.69 -61.00 -90.00   74
 25  ω     34.00 106.00   0.50    0.28    --  106.69-100.00-128.32  144
 26  ω     38.00  70.00   0.50    0.28    --  106.69 -61.00-120.00   64
 27  ω     34.00  71.00   0.50    0.28    --  106.69 -61.00 -60.00   74
 28  ω     34.00 106.00   0.50    0.28    --  106.69 -99.00-159.41  144
 29  ω     35.00  67.00   0.50    0.28    --  106.69 -61.00-150.00   64
 30  ω    -92.00 -18.00   0.50    0.07    --  -46.75 134.00 -53.00  148
 31  ω    -51.00 -16.00   0.50    0.28    --  -88.50  45.00   0.00   70
 32  ω    -51.00 -16.00   0.50    0.28    --  -88.50  45.00 -60.00   70
 33  ω    -92.00 -18.00   0.50    0.28    --  -88.50 134.00 -53.00  148
 34  ω    -94.00 -18.00   0.50    0.07    --  -46.75 135.00 125.00  152
 35  ω    -94.00 -18.00   0.50    0.28    --  -88.50 135.00 125.00  152
 36  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00  60.00   72
 37  ω   -119.00 -67.00   0.50    0.07    --  -46.75-135.00  59.00  104
 38  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00 150.00   72
 39  ω   -160.00 -67.00   0.50    0.28    --  -88.50-135.00  59.00  186
 40  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00 -60.00   72
 41  ω   -119.00 -68.00   0.50    0.07    --  -46.75-134.00-121.00  102
 42  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00-150.00   72
 43  ω   -160.00 -68.00   0.50    0.28    --  -88.50-134.00-121.00  184
 44  ω   -160.00 -78.00   0.50    0.28    --  -88.50 -56.00-113.67  164
 45  ω   -160.00-101.00   0.50    0.28    --  -88.50 -77.00 -90.00  118
 46  ω   -160.00 -73.00   0.50    0.28    --  -88.50 -55.00 116.06  174
 47  ω   -160.00 -91.00   0.50    0.28    --  -88.50 -61.00 150.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225540000
_diffrn_orient_matrix_UB_12      -0.1098875000
_diffrn_orient_matrix_UB_13      -0.0051886000
_diffrn_orient_matrix_UB_21      -0.0395058000
_diffrn_orient_matrix_UB_22      -0.0353319000
_diffrn_orient_matrix_UB_23      0.1079927000
_diffrn_orient_matrix_UB_31      -0.1239714000
_diffrn_orient_matrix_UB_32      0.0532137000
_diffrn_orient_matrix_UB_33      0.0002560000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8008
_reflns_number_total             9064
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         9064
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.058
_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)+(0.0400P)²+1.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1228
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C29-C30 = C26-C27 = C27-C28
 1.37 with sigma of 0.02
 C29-C28
 1.38 with sigma of 0.02
 C30-C31 = C31-C26
 1.36 with sigma of 0.02
 C30-C26
 2.36 with sigma of 0.04
 C29-C31 = C31-C27 = C26-C28
 2.37 with sigma of 0.04
 C29-C27
 2.38 with sigma of 0.04
 C29-C27 \\sim C29-C31 \\sim C27-C31 \\sim C26-C30 \\sim C26-C28 \\sim C28-C30
 with sigma of 0.04
 C29-C30 \\sim C30-C31 \\sim C31-C26 \\sim C26-C27 \\sim C27-C28 \\sim C28-C29
 with sigma of 0.02
3. Restrained planarity
 C29, C30, C31, C26, C27, C28
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C17B) = Uanis(C16A) = Uanis(C16B) = Uanis(C17A)
Uanis(O4) = Uanis(C15)
Uanis(C27) = Uanis(C26) = Uanis(C31) = Uanis(C30) = Uanis(C29) = Uanis(C28)
5. Others
 Fixed Sof: C16A(0.6) H16A(0.6) H16B(0.6) C34A(0.6) H34A(0.6) H34B(0.6)
 H34C(0.6) C33A(0.6) H33A(0.6) H33B(0.6) C17A(0.6) H17A(0.6) H17B(0.6)
 H17C(0.6) C17B(0.4) H17D(0.4) H17E(0.4) H17F(0.4) C16B(0.4) H16C(0.4)
 H16D(0.4) C33B(0.4) H33C(0.4) H33D(0.4) C34B(0.4) H34D(0.4) H34E(0.4)
 H34F(0.4) O3B(0.4) O3A(0.6)
6.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C50(H50A,H50B), C24(H24A,H24B), C7(H7A,H7B), C16A(H16A,H16B),
 C33A(H33A,H33B), C16B(H16C,H16D), C33B(H33C,H33D)
6.b Aromatic/amide H refined with riding coordinates:
 N3(H3A), N1(H1), N2(H2), C44(H44), C48(H48), C37(H37), C47(H47), C46(H46),
 C45(H45), C20(H20), C3(H3), C10(H10), C14(H14), C11(H11), C13(H13), C12(H12),
 C29(H29), C30(H30), C31(H31), C27(H27), C28(H28)
6.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C51(H51A,H51B,H51C), C25(H25A,H25B,H25C), C8(H8A,H8B,
 H8C), C34A(H34A,H34B,H34C), C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F),
 C34B(H34D,H34E,H34F)
;
_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
O12 O 0.59820(9) 0.20782(8) 0.84456(7) 0.0217(2) Uani 1 1 d . . . . .
O9 O 0.49184(10) 0.62156(9) 0.92234(8) 0.0250(2) Uani 1 1 d . . . . .
O11 O 0.44396(10) 0.23620(9) 0.96785(8) 0.0263(3) Uani 1 1 d . . . . .
O6 O 0.78280(11) 0.30446(10) 1.10161(8) 0.0318(3) Uani 1 1 d . . . . .
O10 O 0.49943(13) 0.76674(10) 0.63952(8) 0.0344(3) Uani 1 1 d . . . . .
O5 O 0.74684(11) 0.47996(12) 0.83574(8) 0.0367(3) Uani 1 1 d . . . . .
O1 O 0.75760(11) 0.71847(12) 0.68024(9) 0.0378(3) Uani 1 1 d . . . . .
N3 N 0.49580(11) 0.45693(10) 0.89617(9) 0.0185(3) Uani 1 1 d . . . . .
H3A H 0.491796 0.427346 0.954170 0.022 Uiso 1 1 calc R U . . .
O4 O 0.80241(12) 0.29887(11) 0.61088(9) 0.0414(3) Uani 1 1 d . . . . .
O8 O 0.93722(12) 0.81700(11) 0.86151(12) 0.0548(5) Uani 1 1 d . . . . .
O2 O 0.78119(16) 0.86558(12) 0.39517(10) 0.0507(4) Uani 1 1 d . . . . .
N1 N 0.79942(12) 0.55203(13) 0.64478(10) 0.0331(3) Uani 1 1 d . . . . .
H1 H 0.798670 0.521789 0.702069 0.040 Uiso 1 1 calc R U . . .
O7 O 0.78517(15) 0.85875(12) 0.80557(11) 0.0554(4) Uani 1 1 d . . . . .
N2 N 0.78897(13) 0.62912(13) 0.85873(10) 0.0324(3) Uani 1 1 d . . . . .
H2 H 0.778490 0.666226 0.805656 0.039 Uiso 1 1 calc R U . . .
C36 C 0.49645(13) 0.61536(12) 0.76888(11) 0.0195(3) Uani 1 1 d . . . . .
C35 C 0.49456(13) 0.56946(12) 0.86585(10) 0.0193(3) Uani 1 1 d . . . . .
C39 C 0.50282(12) 0.38920(12) 0.84174(10) 0.0177(3) Uani 1 1 d . . . . .
C49 C 0.50910(13) 0.26932(12) 0.89242(10) 0.0187(3) Uani 1 1 d . . . . .
C43 C 0.49409(13) 0.36506(12) 0.68984(10) 0.0185(3) Uani 1 1 d . . . . .
C38 C 0.50309(12) 0.43103(12) 0.74956(10) 0.0180(3) Uani 1 1 d . . . . .
C44 C 0.55652(13) 0.38221(12) 0.59512(11) 0.0205(3) Uani 1 1 d . . . . .
H44 H 0.606413 0.433448 0.569722 0.025 Uiso 1 1 calc R U . . .
C48 C 0.41705(13) 0.29008(12) 0.72578(11) 0.0198(3) Uani 1 1 d . . . . .
H48 H 0.373591 0.278964 0.788508 0.024 Uiso 1 1 calc R U . . .
C37 C 0.50145(13) 0.54628(12) 0.71542(10) 0.0191(3) Uani 1 1 d . . . . .
H37 H 0.503907 0.576895 0.652888 0.023 Uiso 1 1 calc R U . . .
C47 C 0.40480(14) 0.23207(12) 0.66874(11) 0.0216(3) Uani 1 1 d . . . . .
H47 H 0.353466 0.182206 0.693489 0.026 Uiso 1 1 calc R U . . .
C46 C 0.46884(14) 0.24816(13) 0.57490(11) 0.0234(3) Uani 1 1 d . . . . .
H46 H 0.460975 0.208921 0.536799 0.028 Uiso 1 1 calc R U . . .
C40 C 0.48710(14) 0.73709(12) 0.72359(11) 0.0217(3) Uani 1 1 d . . . . .
C4 C 0.82373(13) 0.52582(15) 0.49473(12) 0.0277(4) Uani 1 1 d . . . . .
C45 C 0.54478(14) 0.32333(13) 0.53835(11) 0.0226(3) Uani 1 1 d . . . . .
H45 H 0.587993 0.334309 0.475564 0.027 Uiso 1 1 calc R U . . .
C20 C 0.81188(13) 0.52041(13) 1.02907(11) 0.0243(3) Uani 1 1 d . . . . .
H20 H 0.816918 0.483697 1.089009 0.029 Uiso 1 1 calc R U . . .
C41 C 0.46010(15) 0.81902(13) 0.78199(11) 0.0249(3) Uani 1 1 d . . . . .
H41A H 0.528680 0.820076 0.796522 0.030 Uiso 1 1 calc R U . . .
H41B H 0.402664 0.795650 0.840752 0.030 Uiso 1 1 calc R U . . .
C9 C 0.84388(14) 0.45929(14) 0.42594(11) 0.0270(4) Uani 1 1 d . . . . .
C23 C 0.78216(14) 0.34253(14) 1.02043(12) 0.0258(3) Uani 1 1 d . . . . .
C50 C 0.61248(15) 0.08930(12) 0.88633(12) 0.0258(3) Uani 1 1 d . . . . .
H50A H 0.589914 0.076825 0.954124 0.031 Uiso 1 1 calc R U . . .
H50B H 0.692580 0.057295 0.865458 0.031 Uiso 1 1 calc R U . . .
C21 C 0.83041(14) 0.63178(14) 0.99560(12) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.80383(14) 0.64242(15) 0.46504(12) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.805746 0.673423 0.402662 0.034 Uiso 1 1 calc R U . . .
C18 C 0.77222(14) 0.52045(15) 0.88774(12) 0.0296(4) Uani 1 1 d . . . . .
C19 C 0.78708(14) 0.46353(14) 0.97892(11) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.76793(14) 0.48386(14) 0.37294(11) 0.0274(4) Uani 1 1 d . . . . .
H10 H 0.705047 0.539621 0.382499 0.033 Uiso 1 1 calc R U . . .
C22 C 0.82058(15) 0.68242(14) 0.90688(12) 0.0307(4) Uani 1 1 d . . . . .
C1 C 0.77725(14) 0.66573(17) 0.62007(12) 0.0323(4) Uani 1 1 d . . . . .
C5 C 0.82230(14) 0.48335(16) 0.58730(12) 0.0304(4) Uani 1 1 d . . . . .
C2 C 0.78200(14) 0.71234(16) 0.52214(12) 0.0294(4) Uani 1 1 d . . . . .
C14 C 0.93813(14) 0.37591(15) 0.40991(12) 0.0321(4) Uani 1 1 d . . . . .
H14 H 0.989699 0.358580 0.444657 0.039 Uiso 1 1 calc R U . . .
C42 C 0.41633(16) 0.93499(13) 0.73338(13) 0.0288(4) Uani 1 1 d . . . . .
H42A H 0.475574 0.961396 0.678224 0.043 Uiso 1 1 calc R U . . .
H42B H 0.395029 0.982956 0.775343 0.043 Uiso 1 1 calc R U . . .
H42C H 0.350751 0.933877 0.715879 0.043 Uiso 1 1 calc R U . . .
C11 C 0.78515(15) 0.42608(15) 0.30616(12) 0.0297(4) Uani 1 1 d . . . . .
H11 H 0.733344 0.442793 0.271705 0.036 Uiso 1 1 calc R U . . .
C13 C 0.95548(16) 0.31871(16) 0.34261(13) 0.0353(4) Uani 1 1 d . . . . .
H13 H 1.018673 0.263392 0.332396 0.042 Uiso 1 1 calc R U . . .
C24 C 0.77926(16) 0.27042(16) 0.96120(13) 0.0330(4) Uani 1 1 d . . . . .
H24A H 0.830406 0.291937 0.898536 0.040 Uiso 1 1 calc R U . . .
H24B H 0.702318 0.282598 0.956065 0.040 Uiso 1 1 calc R U . . .
C6 C 0.76517(16) 0.83439(16) 0.47949(13) 0.0332(4) Uani 1 1 d . . . . .
C12 C 0.87909(16) 0.34347(15) 0.29030(13) 0.0327(4) Uani 1 1 d . . . . .
H12 H 0.890831 0.305067 0.245129 0.039 Uiso 1 1 calc R U . . .
C51 C 0.54116(16) 0.03382(14) 0.85919(13) 0.0320(4) Uani 1 1 d . . . . .
H51A H 0.561038 0.048945 0.792026 0.048 Uiso 1 1 calc R U . . .
H51B H 0.461441 0.061468 0.883988 0.048 Uiso 1 1 calc R U . . .
H51C H 0.555473 -0.044387 0.884211 0.048 Uiso 1 1 calc R U . . .
C15 C 0.84864(17) 0.36335(17) 0.63502(14) 0.0414(3) Uani 1 1 d . . . . .
C32 C 0.84374(18) 0.79711(16) 0.85269(14) 0.0416(5) Uani 1 1 d . . . . .
C25 C 0.81409(19) 0.14862(17) 1.00087(16) 0.0418(5) Uani 1 1 d . . . . .
H25A H 0.804879 0.106400 0.963342 0.063 Uiso 1 1 calc R U . . .
H25B H 0.766594 0.127617 1.064214 0.063 Uiso 1 1 calc R U . . .
H25C H 0.892840 0.134712 1.000161 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7275(2) 0.91548(18) 0.53974(15) 0.0451(5) Uani 1 1 d . . . . .
H7A H 0.786832 0.909155 0.568234 0.054 Uiso 1 1 calc R U . . .
H7B H 0.658928 0.896822 0.589898 0.054 Uiso 1 1 calc R U . . .
C16A C 0.8113(3) 0.1750(3) 0.6496(3) 0.0367(5) Uani 0.6 1 d . . P A 1
H16A H 0.814843 0.156702 0.713636 0.044 Uiso 0.6 1 calc R U P A 1
H16B H 0.743482 0.151318 0.650632 0.044 Uiso 0.6 1 calc R U P A 1
C8 C 0.7027(3) 1.0340(2) 0.48661(19) 0.0685(8) Uani 1 1 d . . . . .
H8A H 0.770778 1.053841 0.437883 0.103 Uiso 1 1 calc R U . . .
H8B H 0.678838 1.081713 0.529009 0.103 Uiso 1 1 calc R U . . .
H8C H 0.642888 1.041377 0.459273 0.103 Uiso 1 1 calc R U . . .
C34A C 1.0833(5) 0.9293(4) 0.7596(3) 0.0384(11) Uani 0.6 1 d . . P B 1
H34A H 1.076718 0.907580 0.708193 0.058 Uiso 0.6 1 calc R U P B 1
H34B H 1.140544 0.877312 0.784769 0.058 Uiso 0.6 1 calc R U P B 1
H34C H 1.104855 1.001319 0.737844 0.058 Uiso 0.6 1 calc R U P B 1
C33A C 0.9702(3) 0.9321(3) 0.8346(3) 0.0330(7) Uani 0.6 1 d . . P B 1
H33A H 0.912500 0.987628 0.811233 0.040 Uiso 0.6 1 calc R U P B 1
H33B H 0.976790 0.949367 0.888664 0.040 Uiso 0.6 1 calc R U P B 1
C17A C 0.9154(3) 0.1151(3) 0.5916(2) 0.0367(5) Uani 0.6 1 d . . P A 1
H17A H 0.911459 0.132388 0.528418 0.055 Uiso 0.6 1 calc R U P A 1
H17B H 0.918831 0.037111 0.617451 0.055 Uiso 0.6 1 calc R U P A 1
H17C H 0.982643 0.137462 0.591522 0.055 Uiso 0.6 1 calc R U P A 1
C17B C 0.7861(5) 0.1291(4) 0.6272(3) 0.0367(5) Uani 0.4 1 d . . P A 2
H17D H 0.813594 0.142204 0.560008 0.055 Uiso 0.4 1 calc R U P A 2
H17E H 0.704712 0.152701 0.646316 0.055 Uiso 0.4 1 calc R U P A 2
H17F H 0.803449 0.051755 0.654289 0.055 Uiso 0.4 1 calc R U P A 2
C16B C 0.8431(5) 0.1922(5) 0.6597(4) 0.0367(5) Uani 0.4 1 d . . P A 2
H16C H 0.816104 0.183335 0.727238 0.044 Uiso 0.4 1 calc R U P A 2
H16D H 0.925965 0.173749 0.639205 0.044 Uiso 0.4 1 calc R U P A 2
C33B C 0.9620(4) 0.9200(4) 0.7877(4) 0.0297(9) Uani 0.4 1 d . . P B 2
H33C H 0.978114 0.909665 0.725158 0.036 Uiso 0.4 1 calc R U P B 2
H33D H 0.900020 0.981298 0.797894 0.036 Uiso 0.4 1 calc R U P B 2
C34B C 1.0642(7) 0.9344(7) 0.8042(6) 0.0490(19) Uani 0.4 1 d . . P B 2
H34D H 1.092309 0.998853 0.760285 0.073 Uiso 0.4 1 calc R U P B 2
H34E H 1.122198 0.870804 0.796260 0.073 Uiso 0.4 1 calc R U P B 2
H34F H 1.045125 0.943158 0.866995 0.073 Uiso 0.4 1 calc R U P B 2
O3B O 0.9137(7) 0.3531(5) 0.6911(6) 0.0362(13) Uani 0.4 1 d . . P C 2
O3A O 0.8978(5) 0.3219(4) 0.6887(4) 0.0411(10) Uani 0.6 1 d . . P C 1
C29 C 0.89805(16) 0.77751(15) 1.18099(14) 0.03634(19) Uani 1 1 d D . . . .
H29 H 0.912301 0.808499 1.221808 0.044 Uiso 1 1 calc R U . . .
C30 C 0.94316(16) 0.66830(15) 1.17780(14) 0.03634(19) Uani 1 1 d D . . . .
H30 H 0.987323 0.625509 1.216821 0.044 Uiso 1 1 calc R U . . .
C31 C 0.92201(16) 0.62344(15) 1.11612(13) 0.03634(19) Uani 1 1 d D . . . .
H31 H 0.953023 0.550400 1.114008 0.044 Uiso 1 1 calc R U . . .
C26 C 0.85536(16) 0.68498(15) 1.05704(14) 0.03634(19) Uani 1 1 d D . . . .
C27 C 0.80900(16) 0.79424(15) 1.06229(14) 0.03634(19) Uani 1 1 d D . . . .
H27 H 0.762657 0.836681 1.024952 0.044 Uiso 1 1 calc R U . . .
C28 C 0.83188(16) 0.83982(15) 1.12316(13) 0.03634(19) Uani 1 1 d D . . . .
H28 H 0.802212 0.913166 1.124893 0.044 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
O12 C49 1.3339(18) . ?
O12 C50 1.4609(18) . ?
O9 C35 1.2457(18) . ?
O11 C49 1.2036(19) . ?
O6 C23 1.217(2) . ?
O10 C40 1.2177(19) . ?
O5 C18 1.245(2) . ?
O1 C1 1.243(2) . ?
N3 H3A 0.8600 . ?
N3 C35 1.3807(19) . ?
N3 C39 1.3583(19) . ?
O4 C15 1.323(3) . ?
O4 C16A 1.518(4) . ?
O4 C16B 1.422(6) . ?
O8 C32 1.324(3) . ?
O8 C33A 1.535(4) . ?
O8 C33B 1.492(4) . ?
O2 C6 1.215(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.379(3) . ?
N1 C5 1.357(2) . ?
O7 C32 1.204(3) . ?
N2 H2 0.8600 . ?
N2 C18 1.381(2) . ?
N2 C22 1.359(3) . ?
C36 C35 1.446(2) . ?
C36 C37 1.369(2) . ?
C36 C40 1.507(2) . ?
C39 C49 1.505(2) . ?
C39 C38 1.377(2) . ?
C43 C38 1.483(2) . ?
C43 C44 1.394(2) . ?
C43 C48 1.398(2) . ?
C38 C37 1.416(2) . ?
C44 H44 0.9300 . ?
C44 C45 1.390(2) . ?
C48 H48 0.9300 . ?
C48 C47 1.388(2) . ?
C37 H37 0.9300 . ?
C47 H47 0.9300 . ?
C47 C46 1.388(2) . ?
C46 H46 0.9300 . ?
C46 C45 1.389(2) . ?
C40 C41 1.498(2) . ?
C4 C9 1.486(3) . ?
C4 C3 1.417(2) . ?
C4 C5 1.380(2) . ?
C45 H45 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.420(2) . ?
C20 C19 1.369(2) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.520(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.395(2) . ?
C23 C19 1.505(2) . ?
C23 C24 1.508(2) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.504(2) . ?
C21 C22 1.378(2) . ?
C21 C26 1.483(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.367(3) . ?
C18 C19 1.446(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C22 C32 1.509(3) . ?
C1 C2 1.452(2) . ?
C5 C15 1.509(3) . ?
C2 C6 1.504(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(3) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.516(3) . ?
C6 C7 1.495(3) . ?
C12 H12 0.9300 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C15 O3B 1.352(8) . ?
C15 O3A 1.139(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.515(3) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16A C17A 1.493(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C34A H34A 0.9600 . ?
C34A H34B 0.9600 . ?
C34A H34C 0.9600 . ?
C34A C33A 1.500(5) . ?
C33A H33A 0.9700 . ?
C33A H33B 0.9700 . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C17B C16B 1.490(7) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C33B H33C 0.9700 . ?
C33B H33D 0.9700 . ?
C33B C34B 1.461(10) . ?
C34B H34D 0.9600 . ?
C34B H34E 0.9600 . ?
C34B H34F 0.9600 . ?
C29 H29 0.9300 . ?
C29 C30 1.388(2) . ?
C29 C28 1.381(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.386(3) . ?
C31 H31 0.9300 . ?
C31 C26 1.396(3) . ?
C26 C27 1.398(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.393(3) . ?
C28 H28 0.9300 . ?

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
C49 O12 C50 116.00(12) . . ?
C35 N3 H3A 117.4 . . ?
C39 N3 H3A 117.4 . . ?
C39 N3 C35 125.24(12) . . ?
C15 O4 C16A 124.3(2) . . ?
C15 O4 C16B 102.0(3) . . ?
C32 O8 C33A 124.40(19) . . ?
C32 O8 C33B 103.7(2) . . ?
C1 N1 H1 116.9 . . ?
C5 N1 H1 116.9 . . ?
C5 N1 C1 126.20(15) . . ?
C18 N2 H2 117.2 . . ?
C22 N2 H2 117.2 . . ?
C22 N2 C18 125.58(15) . . ?
C35 C36 C40 123.60(13) . . ?
C37 C36 C35 119.05(13) . . ?
C37 C36 C40 117.27(13) . . ?
O9 C35 N3 118.79(13) . . ?
O9 C35 C36 126.25(14) . . ?
N3 C35 C36 114.96(13) . . ?
N3 C39 C49 113.53(12) . . ?
N3 C39 C38 120.88(13) . . ?
C38 C39 C49 125.59(13) . . ?
O12 C49 C39 110.92(12) . . ?
O11 C49 O12 125.72(14) . . ?
O11 C49 C39 123.30(14) . . ?
C44 C43 C38 120.53(13) . . ?
C44 C43 C48 118.71(14) . . ?
C48 C43 C38 120.62(13) . . ?
C39 C38 C43 123.95(13) . . ?
C39 C38 C37 115.81(13) . . ?
C37 C38 C43 119.98(13) . . ?
C43 C44 H44 119.7 . . ?
C45 C44 C43 120.52(14) . . ?
C45 C44 H44 119.7 . . ?
C43 C48 H48 119.7 . . ?
C47 C48 C43 120.63(14) . . ?
C47 C48 H48 119.7 . . ?
C36 C37 C38 123.97(14) . . ?
C36 C37 H37 118.0 . . ?
C38 C37 H37 118.0 . . ?
C48 C47 H47 119.9 . . ?
C48 C47 C46 120.28(15) . . ?
C46 C47 H47 119.9 . . ?
C47 C46 H46 120.3 . . ?
C45 C46 C47 119.48(14) . . ?
C45 C46 H46 120.3 . . ?
O10 C40 C36 118.51(14) . . ?
O10 C40 C41 121.29(14) . . ?
C41 C40 C36 120.19(13) . . ?
C3 C4 C9 118.83(14) . . ?
C5 C4 C9 125.22(16) . . ?
C5 C4 C3 115.95(17) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.36(15) . . ?
C46 C45 H45 119.8 . . ?
C21 C20 H20 117.8 . . ?
C19 C20 H20 117.8 . . ?
C19 C20 C21 124.32(15) . . ?
C40 C41 H41A 109.0 . . ?
C40 C41 H41B 109.0 . . ?
C40 C41 C42 112.81(13) . . ?
H41A C41 H41B 107.8 . . ?
C42 C41 H41A 109.0 . . ?
C42 C41 H41B 109.0 . . ?
C10 C9 C4 118.65(15) . . ?
C10 C9 C14 118.71(17) . . ?
C14 C9 C4 122.60(16) . . ?
O6 C23 C19 118.62(15) . . ?
O6 C23 C24 121.22(16) . . ?
C19 C23 C24 120.15(15) . . ?
O12 C50 H50A 109.4 . . ?
O12 C50 H50B 109.4 . . ?
O12 C50 C51 110.98(13) . . ?
H50A C50 H50B 108.0 . . ?
C51 C50 H50A 109.4 . . ?
C51 C50 H50B 109.4 . . ?
C20 C21 C26 119.33(15) . . ?
C22 C21 C20 115.34(16) . . ?
C22 C21 C26 125.32(16) . . ?
C4 C3 H3 117.9 . . ?
C2 C3 C4 124.27(16) . . ?
C2 C3 H3 117.9 . . ?
O5 C18 N2 119.48(16) . . ?
O5 C18 C19 125.86(17) . . ?
N2 C18 C19 114.66(16) . . ?
C20 C19 C23 117.60(14) . . ?
C20 C19 C18 118.99(16) . . ?
C18 C19 C23 123.34(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.64(16) . . ?
C11 C10 H10 119.7 . . ?
N2 C22 C21 120.90(16) . . ?
N2 C22 C32 113.17(16) . . ?
C21 C22 C32 125.92(18) . . ?
O1 C1 N1 119.31(16) . . ?
O1 C1 C2 126.14(18) . . ?
N1 C1 C2 114.53(17) . . ?
N1 C5 C4 120.20(17) . . ?
N1 C5 C15 112.94(15) . . ?
C4 C5 C15 126.81(18) . . ?
C3 C2 C1 118.81(17) . . ?
C3 C2 C6 117.89(15) . . ?
C1 C2 C6 123.30(17) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.49(17) . . ?
C13 C14 H14 119.8 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.45(17) . . ?
C12 C11 H11 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.43(17) . . ?
C12 C13 H13 119.8 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 113.02(15) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
O2 C6 C2 118.54(17) . . ?
O2 C6 C7 120.73(18) . . ?
C7 C6 C2 120.72(16) . . ?
C11 C12 C13 119.28(18) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O4 C15 C5 112.36(16) . . ?
O4 C15 O3B 138.2(3) . . ?
O3B C15 C5 109.4(3) . . ?
O3A C15 O4 116.9(3) . . ?
O3A C15 C5 130.7(3) . . ?
O8 C32 C22 111.17(16) . . ?
O7 C32 O8 126.09(19) . . ?
O7 C32 C22 122.7(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.51(18) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
O4 C16A H16A 109.4 . . ?
O4 C16A H16B 109.4 . . ?
H16A C16A H16B 108.0 . . ?
C17A C16A O4 111.2(3) . . ?
C17A C16A H16A 109.4 . . ?
C17A C16A H16B 109.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H34A C34A H34B 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C33A C34A H34A 109.5 . . ?
C33A C34A H34B 109.5 . . ?
C33A C34A H34C 109.5 . . ?
O8 C33A H33A 110.4 . . ?
O8 C33A H33B 110.4 . . ?
C34A C33A O8 106.7(3) . . ?
C34A C33A H33A 110.4 . . ?
C34A C33A H33B 110.4 . . ?
H33A C33A H33B 108.6 . . ?
C16A C17A H17A 109.5 . . ?
C16A C17A H17B 109.5 . . ?
C16A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
O4 C16B C17B 96.7(4) . . ?
O4 C16B H16C 112.4 . . ?
O4 C16B H16D 112.4 . . ?
C17B C16B H16C 112.4 . . ?
C17B C16B H16D 112.4 . . ?
H16C C16B H16D 110.0 . . ?
O8 C33B H33C 112.0 . . ?
O8 C33B H33D 112.0 . . ?
H33C C33B H33D 109.6 . . ?
C34B C33B O8 99.1(4) . . ?
C34B C33B H33C 112.0 . . ?
C34B C33B H33D 112.0 . . ?
C33B C34B H34D 109.5 . . ?
C33B C34B H34E 109.5 . . ?
C33B C34B H34F 109.5 . . ?
H34D C34B H34E 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C28 C29 C30 119.57(19) . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.6(2) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.1 . . ?
C30 C31 C26 121.75(18) . . ?
C26 C31 H31 119.1 . . ?
C31 C26 C21 119.75(16) . . ?
C31 C26 C27 117.90(18) . . ?
C27 C26 C21 122.25(19) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(2) . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 120.85(18) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?

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
O6 C23 C19 C20 11.0(2) . . . . ?
O6 C23 C19 C18 -171.88(16) . . . . ?
O6 C23 C24 C25 -17.9(2) . . . . ?
O10 C40 C41 C42 17.0(2) . . . . ?
O5 C18 C19 C20 -178.14(16) . . . . ?
O5 C18 C19 C23 4.8(3) . . . . ?
O1 C1 C2 C3 -179.47(17) . . . . ?
O1 C1 C2 C6 1.1(3) . . . . ?
N3 C39 C49 O12 -127.81(13) . . . . ?
N3 C39 C49 O11 49.4(2) . . . . ?
N3 C39 C38 C43 -171.06(14) . . . . ?
N3 C39 C38 C37 3.0(2) . . . . ?
O2 C6 C7 C8 5.1(3) . . . . ?
N1 C1 C2 C3 1.9(2) . . . . ?
N1 C1 C2 C6 -177.52(15) . . . . ?
N1 C5 C15 O4 140.12(16) . . . . ?
N1 C5 C15 O3B -39.8(5) . . . . ?
N1 C5 C15 O3A -37.4(5) . . . . ?
N2 C18 C19 C20 2.1(2) . . . . ?
N2 C18 C19 C23 -174.96(14) . . . . ?
N2 C22 C32 O8 -137.04(17) . . . . ?
N2 C22 C32 O7 40.5(2) . . . . ?
C36 C40 C41 C42 -161.34(14) . . . . ?
C35 N3 C39 C49 176.75(13) . . . . ?
C35 N3 C39 C38 -3.6(2) . . . . ?
C35 C36 C37 C38 1.1(2) . . . . ?
C35 C36 C40 O10 173.79(15) . . . . ?
C35 C36 C40 C41 -7.8(2) . . . . ?
C39 N3 C35 O9 -177.52(14) . . . . ?
C39 N3 C35 C36 2.6(2) . . . . ?
C39 C38 C37 C36 -1.9(2) . . . . ?
C49 O12 C50 C51 85.40(17) . . . . ?
C49 C39 C38 C43 8.5(2) . . . . ?
C49 C39 C38 C37 -177.41(13) . . . . ?
C43 C38 C37 C36 172.44(14) . . . . ?
C43 C44 C45 C46 1.3(2) . . . . ?
C43 C48 C47 C46 -0.2(2) . . . . ?
C38 C39 C49 O12 52.60(19) . . . . ?
C38 C39 C49 O11 -130.15(17) . . . . ?
C38 C43 C44 C45 -177.55(14) . . . . ?
C38 C43 C48 C47 177.01(13) . . . . ?
C44 C43 C38 C39 -142.36(15) . . . . ?
C44 C43 C38 C37 43.8(2) . . . . ?
C44 C43 C48 C47 1.4(2) . . . . ?
C48 C43 C38 C39 42.1(2) . . . . ?
C48 C43 C38 C37 -131.76(15) . . . . ?
C48 C43 C44 C45 -1.9(2) . . . . ?
C48 C47 C46 C45 -0.4(2) . . . . ?
C37 C36 C35 O9 178.86(15) . . . . ?
C37 C36 C35 N3 -1.2(2) . . . . ?
C37 C36 C40 O10 -9.4(2) . . . . ?
C37 C36 C40 C41 168.98(15) . . . . ?
C47 C46 C45 C44 -0.1(2) . . . . ?
C40 C36 C35 O9 -4.4(3) . . . . ?
C40 C36 C35 N3 175.49(13) . . . . ?
C40 C36 C37 C38 -175.88(14) . . . . ?
C4 C9 C10 C11 178.19(15) . . . . ?
C4 C9 C14 C13 -177.69(16) . . . . ?
C4 C3 C2 C1 -0.7(3) . . . . ?
C4 C3 C2 C6 178.70(15) . . . . ?
C4 C5 C15 O4 -42.2(3) . . . . ?
C4 C5 C15 O3B 137.9(5) . . . . ?
C4 C5 C15 O3A 140.2(5) . . . . ?
C20 C21 C22 N2 3.5(2) . . . . ?
C20 C21 C22 C32 -175.64(15) . . . . ?
C20 C21 C26 C31 36.4(2) . . . . ?
C20 C21 C26 C27 -139.87(17) . . . . ?
C9 C4 C3 C2 178.64(16) . . . . ?
C9 C4 C5 N1 -177.93(15) . . . . ?
C9 C4 C5 C15 4.6(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C9 C14 C13 C12 -0.1(3) . . . . ?
C50 O12 C49 O11 3.6(2) . . . . ?
C50 O12 C49 C39 -179.25(12) . . . . ?
C21 C20 C19 C23 173.69(15) . . . . ?
C21 C20 C19 C18 -3.5(2) . . . . ?
C21 C22 C32 O8 42.1(2) . . . . ?
C21 C22 C32 O7 -140.3(2) . . . . ?
C21 C26 C27 C28 177.99(16) . . . . ?
C3 C4 C9 C10 -49.4(2) . . . . ?
C3 C4 C9 C14 128.15(17) . . . . ?
C3 C4 C5 N1 1.9(2) . . . . ?
C3 C4 C5 C15 -175.57(17) . . . . ?
C3 C2 C6 O2 -6.2(3) . . . . ?
C3 C2 C6 C7 172.75(17) . . . . ?
C18 N2 C22 C21 -5.1(3) . . . . ?
C18 N2 C22 C32 174.11(15) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C19 C20 C21 C26 179.28(16) . . . . ?
C19 C23 C24 C25 160.71(16) . . . . ?
C10 C9 C14 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C22 N2 C18 O5 -177.67(16) . . . . ?
C22 N2 C18 C19 2.1(2) . . . . ?
C22 C21 C26 C31 -145.17(18) . . . . ?
C22 C21 C26 C27 38.5(3) . . . . ?
C1 N1 C5 C4 -0.7(3) . . . . ?
C1 N1 C5 C15 177.10(16) . . . . ?
C1 C2 C6 O2 173.25(18) . . . . ?
C1 C2 C6 C7 -7.8(3) . . . . ?
C5 N1 C1 O1 -179.98(16) . . . . ?
C5 N1 C1 C2 -1.2(2) . . . . ?
C5 C4 C9 C10 130.38(18) . . . . ?
C5 C4 C9 C14 -52.0(2) . . . . ?
C5 C4 C3 C2 -1.2(2) . . . . ?
C2 C6 C7 C8 -173.8(2) . . . . ?
C14 C9 C10 C11 0.5(2) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C24 C23 C19 C20 -167.58(15) . . . . ?
C24 C23 C19 C18 9.5(2) . . . . ?
C15 O4 C16A C17A -89.3(3) . . . . ?
C15 O4 C16B C17B -180.0(3) . . . . ?
C32 O8 C33A C34A -119.1(3) . . . . ?
C32 O8 C33B C34B 179.5(5) . . . . ?
C16A O4 C15 C5 -178.2(2) . . . . ?
C16A O4 C15 O3A -0.3(5) . . . . ?
C33A O8 C32 O7 16.9(4) . . . . ?
C33A O8 C32 C22 -165.7(2) . . . . ?
C16B O4 C15 C5 177.2(3) . . . . ?
C16B O4 C15 O3B -3.0(7) . . . . ?
C33B O8 C32 O7 -10.2(3) . . . . ?
C33B O8 C32 C22 167.3(3) . . . . ?
C29 C30 C31 C26 -0.5(3) . . . . ?
C30 C29 C28 C27 0.6(3) . . . . ?
C30 C31 C26 C21 -177.01(16) . . . . ?
C30 C31 C26 C27 -0.6(3) . . . . ?
C31 C26 C27 C28 1.6(3) . . . . ?
C26 C21 C22 N2 -174.99(16) . . . . ?
C26 C21 C22 C32 5.9(3) . . . . ?
C26 C27 C28 C29 -1.7(3) . . . . ?
C28 C29 C30 C31 0.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.750
####################################################################### 
# 
# 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_hpd750_try2_auto
_database_code_depnum_ccdc_archive 'CCDC 2292359'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-01-05 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2024-01-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H26 N2 O5'
_chemical_formula_sum            'C29 H26 N2 O5'
_chemical_formula_weight         482.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'Soumen Mystery'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.83436(15)
_cell_length_b                   11.10289(10)
_cell_length_c                   20.5729(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.0934(12)
_cell_angle_gamma                90
_cell_volume                     2986.19(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18475
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1120
_cell_measurement_theta_min      4.5320
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 -2 0.0976
9 -1 -1 0.0787
-5 -6 3 0.1160
-8 1 0 0.0861
-2 1 13 0.0711
2 -6 5 0.0884
3 -2 -13 0.0169

_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.1
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0099 7.0696 -2.4548 0.0846 0.3429 0.9355
8.5898 -0.6672 -0.6858 0.2037 0.8514 -0.4834
-4.6129 -6.1773 2.6367 -0.1874 -0.7733 -0.6057
-8.4125 1.3986 0.4130 -0.1906 -0.7978 0.5720
-2.2829 1.3124 13.0976 0.9722 -0.2339 -0.0089
2.4744 -6.0107 4.8301 0.2182 -0.0503 -0.9746
2.6101 -2.0215 -12.8149 -0.9672 0.2329 -0.1016

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.375
_diffrn_reflns_theta_min         3.381
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     91.00 178.00   0.50    0.30    --  106.40  34.00 -50.00  174
  2  ω     31.00  95.00   0.50    0.08    --   46.79  53.00  40.47  128
  3  ω     32.00 121.00   0.50    0.08    --   46.79  34.00 -50.00  178
  4  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00-180.00   74
  5  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00-150.00   74
  6  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00-120.00   74
  7  ω     34.00 101.00   0.50    0.30    --  106.40 -77.00   0.00  134
  8  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00  90.00   74
  9  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00 150.00   74
 10  ω    -27.00  40.00   0.50    0.08    --   46.79 -34.00 151.00  134
 11  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00   0.00   74
 12  ω     36.00 105.00   0.50    0.30    --  106.40 -98.00 -35.52  138
 13  ω    -30.00  29.00   0.50    0.08    --  -46.79  19.00  90.00  118
 14  ω    -40.00  28.00   0.50    0.08    --  -46.79  34.00 -50.00  136
 15  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00-180.00  142
 16  ω    -71.00 -19.00   0.50    0.30    --  -91.75  61.00 120.00  104
 17  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 150.00   64
 18  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 120.00   64
 19  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00  90.00   64
 20  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00  30.00   64
 21  ω   -166.00 -76.00   0.50    0.30    --  -91.75 -34.00 151.00  180
 22  ω   -164.00-101.00   0.50    0.30    --  -91.75 -77.00  90.00  126
 23  ω   -121.00 -32.00   0.50    0.08    --  -46.79 -34.00 151.00  178
 24  ω   -164.00-100.00   0.50    0.30    --  -91.75 -94.00 -90.00  128
 25  ω    -85.00 -13.00   0.50    0.08    --  -46.79 125.00-180.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0327711000
_diffrn_orient_matrix_UB_12      0.0383444000
_diffrn_orient_matrix_UB_13      0.0760993000
_diffrn_orient_matrix_UB_21      0.1023703000
_diffrn_orient_matrix_UB_22      0.0467322000
_diffrn_orient_matrix_UB_23      -0.0046956000
_diffrn_orient_matrix_UB_31      -0.0482962000
_diffrn_orient_matrix_UB_32      0.1248965000
_diffrn_orient_matrix_UB_33      -0.0216141000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5335
_reflns_number_total             5981
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         5981
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.011
_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)+(0.0679P)²+1.1647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H28C,H28D,H1} of C28B, All C(H,H) groups
 At 1.5 times of:
  {H20A,H20B,H20C} of C20, {H8A,H8B,H8C} of C8, {H29A,H29B,H29C} of C29A,
  {H29D,H29E,H29F} of C29B
2. Others
 Fixed Sof: O5A(0.75) C28A(0.75) H28A(0.75) H28B(0.75) C29A(0.75) H29A(0.75)
 H29B(0.75) H29C(0.75) C29B(0.25) H29D(0.25) H29E(0.25) H29F(0.25) O5B(0.25)
 C28B(0.25) H28C(0.25) H28D(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C28A(H28A,H28B), C28B(H28C,H28D)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C14(H14), C11(H11), C17(H17), C12(H12), C22(H22), C13(H13),
 C26(H26), C23(H23), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C8(H8A,H8B,H8C), C29A(H29A,H29B,H29C), C29B(H29D,H29E,
 H29F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.61937(7) 0.63578(8) 0.63694(4) 0.0254(2) Uani 1 1 d . . . . .
O1 O 0.59730(7) 0.82735(8) 0.66600(5) 0.0302(2) Uani 1 1 d . . . . .
O3 O 0.38008(7) 0.97720(8) 0.44365(5) 0.0316(2) Uani 1 1 d . . . . .
O4 O -0.11375(8) 0.81388(11) 0.32599(6) 0.0442(3) Uani 1 1 d . . . . .
N1 N 0.46780(8) 0.84945(10) 0.52867(5) 0.0246(2) Uani 1 1 d . . . . .
N2 N 0.13713(8) 0.75952(10) 0.38587(6) 0.0272(2) Uani 1 1 d . . . . .
O5A O -0.0499(3) 0.6382(3) 0.37698(12) 0.0378(6) Uani 0.75 1 d . . P A 1
C9 C 0.41540(9) 0.53928(11) 0.58186(6) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.41046(9) 0.65242(11) 0.54266(6) 0.0224(2) Uani 1 1 d . . . . .
C3 C 0.32829(9) 0.67270(12) 0.48081(6) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.279167 0.610570 0.464214 0.029 Uiso 1 1 calc R U . . .
C1 C 0.48044(9) 0.74351(11) 0.56428(6) 0.0225(2) Uani 1 1 d . . . . .
C6 C 0.57214(9) 0.74140(11) 0.62844(6) 0.0234(3) Uani 1 1 d . . . . .
C5 C 0.38771(9) 0.87503(12) 0.46979(6) 0.0253(3) Uani 1 1 d . . . . .
C4 C 0.31644(9) 0.77722(12) 0.44400(6) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.41166(10) 0.42805(12) 0.54995(7) 0.0267(3) Uani 1 1 d . . . . .
H10 H 0.405800 0.424378 0.502680 0.032 Uiso 1 1 calc R U . . .
C15 C 0.22775(9) 0.79061(11) 0.37952(7) 0.0253(3) Uani 1 1 d . . . . .
C14 C 0.42181(10) 0.54314(12) 0.65110(7) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.422928 0.618671 0.673032 0.033 Uiso 1 1 calc R U . . .
C16 C 0.23859(10) 0.82360(12) 0.31650(7) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.70287(10) 0.62041(12) 0.70204(7) 0.0286(3) Uani 1 1 d . . . . .
H7A H 0.679586 0.641650 0.741247 0.034 Uiso 1 1 calc R U . . .
H7B H 0.761254 0.672979 0.703280 0.034 Uiso 1 1 calc R U . . .
C11 C 0.41648(11) 0.32213(13) 0.58710(7) 0.0323(3) Uani 1 1 d . . . . .
H11 H 0.414399 0.246391 0.565204 0.039 Uiso 1 1 calc R U . . .
C17 C 0.15099(11) 0.81854(12) 0.25874(7) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.155804 0.838084 0.214948 0.036 Uiso 1 1 calc R U . . .
C21 C -0.03391(10) 0.76878(13) 0.20090(7) 0.0303(3) Uani 1 1 d . . . . .
C19 C 0.05426(10) 0.76022(12) 0.32952(7) 0.0284(3) Uani 1 1 d . . . . .
C18 C 0.05673(10) 0.78556(12) 0.26369(7) 0.0289(3) Uani 1 1 d . . . . .
C20 C 0.33959(11) 0.85452(14) 0.30813(7) 0.0345(3) Uani 1 1 d . . . . .
H20A H 0.353575 0.940508 0.317259 0.052 Uiso 1 1 calc R U . . .
H20B H 0.337172 0.836119 0.261035 0.052 Uiso 1 1 calc R U . . .
H20C H 0.393910 0.807103 0.340641 0.052 Uiso 1 1 calc R U . . .
C27 C -0.04615(10) 0.74086(14) 0.34145(7) 0.0342(3) Uani 1 1 d . . . . .
C12 C 0.42433(11) 0.32692(13) 0.65602(8) 0.0338(3) Uani 1 1 d . . . . .
H12 H 0.428198 0.254517 0.681349 0.041 Uiso 1 1 calc R U . . .
C22 C -0.06554(11) 0.85950(14) 0.15151(7) 0.0327(3) Uani 1 1 d . . . . .
H22 H -0.030645 0.934548 0.158539 0.039 Uiso 1 1 calc R U . . .
C13 C 0.42653(10) 0.43748(13) 0.68798(7) 0.0313(3) Uani 1 1 d . . . . .
H13 H 0.431258 0.440767 0.735069 0.038 Uiso 1 1 calc R U . . .
C26 C -0.08571(11) 0.65893(14) 0.18937(8) 0.0366(3) Uani 1 1 d . . . . .
H26 H -0.064410 0.596491 0.222580 0.044 Uiso 1 1 calc R U . . .
C8 C 0.73417(12) 0.49020(13) 0.70613(8) 0.0388(3) Uani 1 1 d . . . . .
H8A H 0.758215 0.470838 0.667530 0.058 Uiso 1 1 calc R U . . .
H8B H 0.675381 0.439213 0.703980 0.058 Uiso 1 1 calc R U . . .
H8C H 0.789324 0.475680 0.749562 0.058 Uiso 1 1 calc R U . . .
C23 C -0.14805(12) 0.84015(16) 0.09204(8) 0.0394(4) Uani 1 1 d . . . . .
H23 H -0.169643 0.902309 0.058679 0.047 Uiso 1 1 calc R U . . .
C24 C -0.19888(11) 0.73090(17) 0.08118(8) 0.0426(4) Uani 1 1 d . . . . .
H24 H -0.254973 0.718131 0.040306 0.051 Uiso 1 1 calc R U . . .
C25 C -0.16809(12) 0.63984(16) 0.12988(8) 0.0418(4) Uani 1 1 d . . . . .
H25 H -0.203170 0.564916 0.122552 0.050 Uiso 1 1 calc R U . . .
C28A C -0.1465(3) 0.6134(4) 0.3886(2) 0.0547(11) Uani 0.75 1 d . . P A 1
H28A H -0.202666 0.608205 0.344053 0.066 Uiso 0.75 1 calc R U P A 1
H28B H -0.162611 0.678982 0.416008 0.066 Uiso 0.75 1 calc R U P A 1
C29A C -0.13620(17) 0.4974(3) 0.42607(12) 0.0498(6) Uani 0.75 1 d . . P A 1
H29A H -0.116838 0.433915 0.399626 0.075 Uiso 0.75 1 calc R U P A 1
H29B H -0.201604 0.476767 0.432113 0.075 Uiso 0.75 1 calc R U P A 1
H29C H -0.083349 0.505016 0.471224 0.075 Uiso 0.75 1 calc R U P A 1
C29B C -0.1556(6) 0.6299(11) 0.4264(5) 0.065(3) Uani 0.25 1 d . . P A 2
H29D H -0.156048 0.717779 0.430869 0.098 Uiso 0.25 1 calc R U P A 2
H29E H -0.094526 0.597022 0.460996 0.098 Uiso 0.25 1 calc R U P A 2
H29F H -0.216931 0.596240 0.433345 0.098 Uiso 0.25 1 calc R U P A 2
O5B O -0.0560(8) 0.6266(9) 0.3509(4) 0.0362(17) Uani 0.25 1 d . . P A 2
C28B C -0.1544(9) 0.5989(10) 0.3591(6) 0.043(2) Uani 0.25 1 d . . P A 2
H28C H -0.209121 0.643853 0.324326 0.051 Uiso 0.25 1 calc R U P A 2
H28D H -0.168780 0.511790 0.351164 0.051 Uiso 0.25 1 calc R U P A 2
H1 H 0.5174(16) 0.9080(19) 0.5421(10) 0.051 Uiso 1 1 d . 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
O2 C6 1.3259(16) . ?
O2 C7 1.4646(14) . ?
O1 C6 1.2055(15) . ?
O3 C5 1.2451(16) . ?
O4 C27 1.1993(18) . ?
N1 C1 1.3663(16) . ?
N1 C5 1.3776(15) . ?
N1 H1 0.92(2) . ?
N2 C15 1.3473(17) . ?
N2 C19 1.3375(16) . ?
O5A C27 1.364(4) . ?
O5A C28A 1.459(5) . ?
C9 C2 1.4822(17) . ?
C9 C10 1.3916(18) . ?
C9 C14 1.3987(18) . ?
C2 C3 1.4199(16) . ?
C2 C1 1.3697(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3658(18) . ?
C1 C6 1.5023(16) . ?
C5 C4 1.4459(17) . ?
C4 C15 1.4910(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3922(19) . ?
C15 C16 1.4017(19) . ?
C14 H14 0.9500 . ?
C14 C13 1.3869(19) . ?
C16 C17 1.3934(18) . ?
C16 C20 1.5025(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.504(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C21 C18 1.4887(17) . ?
C21 C22 1.396(2) . ?
C21 C26 1.395(2) . ?
C19 C18 1.395(2) . ?
C19 C27 1.503(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C27 O5B 1.298(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3901(19) . ?
C13 H13 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.389(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.383(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9500 . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C28A C29A 1.484(5) . ?
C29A H29A 0.9800 . ?
C29A H29B 0.9800 . ?
C29A H29C 0.9800 . ?
C29B H29D 0.9800 . ?
C29B H29E 0.9800 . ?
C29B H29F 0.9800 . ?
C29B C28B 1.431(13) . ?
O5B C28B 1.459(16) . ?
C28B H28C 0.9900 . ?
C28B H28D 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
C6 O2 C7 115.52(10) . . ?
C1 N1 C5 125.03(11) . . ?
C1 N1 H1 119.7(13) . . ?
C5 N1 H1 115.1(13) . . ?
C19 N2 C15 118.38(12) . . ?
C27 O5A C28A 116.3(3) . . ?
C10 C9 C2 120.49(11) . . ?
C10 C9 C14 119.19(12) . . ?
C14 C9 C2 120.30(11) . . ?
C3 C2 C9 120.20(11) . . ?
C1 C2 C9 123.17(11) . . ?
C1 C2 C3 116.58(11) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 C2 123.18(11) . . ?
C4 C3 H3 118.4 . . ?
N1 C1 C2 120.58(11) . . ?
N1 C1 C6 114.06(10) . . ?
C2 C1 C6 125.30(11) . . ?
O2 C6 C1 111.58(10) . . ?
O1 C6 O2 126.10(11) . . ?
O1 C6 C1 122.32(11) . . ?
O3 C5 N1 119.86(11) . . ?
O3 C5 C4 125.07(11) . . ?
N1 C5 C4 115.06(11) . . ?
C3 C4 C5 119.41(11) . . ?
C3 C4 C15 119.51(11) . . ?
C5 C4 C15 121.03(11) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.20(12) . . ?
C11 C10 H10 119.9 . . ?
N2 C15 C4 114.15(11) . . ?
N2 C15 C16 122.77(11) . . ?
C16 C15 C4 122.90(12) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.48(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C16 C20 123.40(11) . . ?
C17 C16 C15 116.86(12) . . ?
C17 C16 C20 119.58(12) . . ?
O2 C7 H7A 110.4 . . ?
O2 C7 H7B 110.4 . . ?
O2 C7 C8 106.85(11) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.16(13) . . ?
C12 C11 H11 119.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.55(13) . . ?
C18 C17 H17 119.2 . . ?
C22 C21 C18 121.05(12) . . ?
C26 C21 C18 119.81(12) . . ?
C26 C21 C22 119.08(13) . . ?
N2 C19 C18 123.82(13) . . ?
N2 C19 C27 115.69(12) . . ?
C18 C19 C27 120.33(11) . . ?
C17 C18 C21 120.91(13) . . ?
C17 C18 C19 116.48(12) . . ?
C19 C18 C21 122.42(13) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C27 O5A 122.9(2) . . ?
O4 C27 C19 122.83(14) . . ?
O4 C27 O5B 126.1(5) . . ?
O5A C27 C19 113.98(18) . . ?
O5B C27 C19 108.2(4) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.03(13) . . ?
C13 C12 H12 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.06(14) . . ?
C23 C22 H22 120.0 . . ?
C14 C13 C12 119.93(12) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.73(14) . . ?
C25 C26 H26 119.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.36(14) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.14(13) . . ?
C25 C24 H24 119.9 . . ?
C26 C25 H25 120.2 . . ?
C24 C25 C26 119.63(15) . . ?
C24 C25 H25 120.2 . . ?
O5A C28A H28A 110.1 . . ?
O5A C28A H28B 110.1 . . ?
O5A C28A C29A 108.1(3) . . ?
H28A C28A H28B 108.4 . . ?
C29A C28A H28A 110.1 . . ?
C29A C28A H28B 110.1 . . ?
C28A C29A H29A 109.5 . . ?
C28A C29A H29B 109.5 . . ?
C28A C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
H29D C29B H29E 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
C28B C29B H29D 109.5 . . ?
C28B C29B H29E 109.5 . . ?
C28B C29B H29F 109.5 . . ?
C27 O5B C28B 111.8(8) . . ?
C29B C28B O5B 111.6(10) . . ?
C29B C28B H28C 109.3 . . ?
C29B C28B H28D 109.3 . . ?
O5B C28B H28C 109.3 . . ?
O5B C28B H28D 109.3 . . ?
H28C C28B H28D 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
O3 C5 C4 C3 -174.15(13) . . . . ?
O3 C5 C4 C15 3.2(2) . . . . ?
O4 C27 O5B C28B -15.6(9) . . . . ?
N1 C1 C6 O2 -140.30(11) . . . . ?
N1 C1 C6 O1 39.39(17) . . . . ?
N1 C5 C4 C3 4.51(18) . . . . ?
N1 C5 C4 C15 -178.16(11) . . . . ?
N2 C15 C16 C17 -2.5(2) . . . . ?
N2 C15 C16 C20 -177.90(13) . . . . ?
N2 C19 C18 C17 -3.9(2) . . . . ?
N2 C19 C18 C21 171.12(12) . . . . ?
N2 C19 C27 O4 119.40(15) . . . . ?
N2 C19 C27 O5A -54.9(2) . . . . ?
N2 C19 C27 O5B -78.6(4) . . . . ?
C9 C2 C3 C4 176.72(12) . . . . ?
C9 C2 C1 N1 -175.07(11) . . . . ?
C9 C2 C1 C6 1.69(19) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C9 C14 C13 C12 -0.4(2) . . . . ?
C2 C9 C10 C11 179.91(12) . . . . ?
C2 C9 C14 C13 -179.95(12) . . . . ?
C2 C3 C4 C5 -2.67(19) . . . . ?
C2 C3 C4 C15 179.96(12) . . . . ?
C2 C1 C6 O2 42.75(17) . . . . ?
C2 C1 C6 O1 -137.55(14) . . . . ?
C3 C2 C1 N1 2.51(18) . . . . ?
C3 C2 C1 C6 179.27(11) . . . . ?
C3 C4 C15 N2 48.48(17) . . . . ?
C3 C4 C15 C16 -126.77(14) . . . . ?
C1 N1 C5 O3 175.61(13) . . . . ?
C1 N1 C5 C4 -3.12(19) . . . . ?
C1 C2 C3 C4 -0.94(19) . . . . ?
C6 O2 C7 C8 171.15(12) . . . . ?
C5 N1 C1 C2 -0.42(19) . . . . ?
C5 N1 C1 C6 -177.52(12) . . . . ?
C5 C4 C15 N2 -128.85(13) . . . . ?
C5 C4 C15 C16 55.90(18) . . . . ?
C4 C15 C16 C17 172.38(12) . . . . ?
C4 C15 C16 C20 -3.0(2) . . . . ?
C10 C9 C2 C3 54.49(17) . . . . ?
C10 C9 C2 C1 -128.01(14) . . . . ?
C10 C9 C14 C13 1.33(19) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C15 N2 C19 C18 3.3(2) . . . . ?
C15 N2 C19 C27 -172.17(12) . . . . ?
C15 C16 C17 C18 1.7(2) . . . . ?
C14 C9 C2 C3 -124.21(13) . . . . ?
C14 C9 C2 C1 53.29(17) . . . . ?
C14 C9 C10 C11 -1.38(19) . . . . ?
C16 C17 C18 C21 -173.89(13) . . . . ?
C16 C17 C18 C19 1.2(2) . . . . ?
C7 O2 C6 O1 6.92(19) . . . . ?
C7 O2 C6 C1 -173.40(10) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C21 C22 C23 C24 -0.4(2) . . . . ?
C21 C26 C25 C24 0.3(3) . . . . ?
C19 N2 C15 C4 -175.22(11) . . . . ?
C19 N2 C15 C16 0.04(19) . . . . ?
C19 C27 O5B C28B -176.9(6) . . . . ?
C18 C21 C22 C23 177.57(14) . . . . ?
C18 C21 C26 C25 -177.57(15) . . . . ?
C18 C19 C27 O4 -56.2(2) . . . . ?
C18 C19 C27 O5A 129.46(17) . . . . ?
C18 C19 C27 O5B 105.7(4) . . . . ?
C20 C16 C17 C18 177.35(13) . . . . ?
C27 O5A C28A C29A 178.5(2) . . . . ?
C27 C19 C18 C17 171.37(13) . . . . ?
C27 C19 C18 C21 -13.6(2) . . . . ?
C27 O5B C28B C29B -77.1(11) . . . . ?
C22 C21 C18 C17 -54.2(2) . . . . ?
C22 C21 C18 C19 131.03(15) . . . . ?
C22 C21 C26 C25 -0.4(2) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C26 C21 C18 C17 122.92(16) . . . . ?
C26 C21 C18 C19 -51.9(2) . . . . ?
C26 C21 C22 C23 0.5(2) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C28A O5A C27 O4 7.1(3) . . . . ?
C28A O5A C27 C19 -178.6(3) . . . . ?

_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 0.000 0.000 0.500 349.5 97.7 '2 C4H8O2'
2 0.000 0.500 0.000 349.5 97.7 '2 C4H8O2'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.876
_oxdiff_exptl_absorpt_empirical_full_min 0.613
####################################################################### 
# 
# 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_hpd614c_auto
_database_code_depnum_ccdc_archive 'CCDC 2284794'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2023-07-26 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O5'
_chemical_formula_sum            'C16 H15 N O5'
_chemical_formula_weight         301.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB-1-65B
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.6843(2)
_cell_length_b                   6.33089(7)
_cell_length_c                   15.89366(18)
_cell_angle_alpha                90
_cell_angle_beta                 114.7584(15)
_cell_angle_gamma                90
_cell_volume                     1433.11(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17076
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8480
_cell_measurement_theta_min      3.3080
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 10 0.0609
-3 -4 0 0.0617
3 1 -10 0.0477
2 3 4 0.0652
-4 0 10 0.0613
-9 1 0 0.0473
5 -1 -10 0.0438
8 -1 2 0.0386

_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.096
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.9947 -0.7351 10.0699 0.0474 0.1873 0.9812
-3.3374 -3.8519 0.3250 0.2336 0.9715 -0.0393
3.0295 0.7807 -10.0542 -0.0501 -0.1987 -0.9788
1.9278 3.4136 4.0830 -0.2058 -0.8602 0.4666
-4.3569 0.3302 10.2858 0.2159 -0.0541 0.9749
-8.7711 1.3973 0.1927 0.9587 -0.2302 -0.1670
5.4539 -0.5110 -10.1424 -0.3401 0.0839 -0.9366
7.6015 -1.2975 2.2578 -0.8928 0.2138 0.3964

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.475
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     83.00 119.00   0.50    0.07    --   46.54  57.00   0.00   72
  2  ω     83.00 119.00   0.50    0.07    --   46.54  57.00  60.00   72
  3  ω     31.00 119.00   0.50    0.07    --   46.54  54.00 153.90  176
  4  ω     31.00 119.00   0.50    0.07    --   46.54  55.00  46.91  176
  5  ω     31.00 119.00   0.50    0.07    --   46.54  54.00 -51.19  176
  6  ω     31.00 119.00   0.50    0.07    --   46.54  54.00-116.64  176
  7  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00   0.00  142
  8  ω     39.00 100.00   0.50    0.07    --   46.54-134.00  63.00  122
  9  ω     39.00 118.00   0.50    0.30    --  106.40-134.00  63.00  158
 10  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00 120.00  142
 11  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00  90.00  142
 12  ω     39.00 100.00   0.50    0.07    --   46.54-134.00-116.00  122
 13  ω     39.00 118.00   0.50    0.30    --  106.40-134.00-116.00  158
 14  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00-120.00  142
 15  ω     34.00 105.00   0.50    0.30    --  106.40 -94.00-150.00  142
 16  ω     34.00 101.00   0.50    0.30    --  106.40 -77.00-120.00  134
 17  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00 -90.00   74
 18  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00   0.00   74
 19  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00  30.00   74
 20  ω     34.00  71.00   0.50    0.30    --  106.40 -61.00  60.00   74
 21  ω     89.00 178.00   0.50    0.30    --  106.40  15.00-150.00  178
 22  ω     89.00 178.00   0.50    0.30    --  106.40 134.00 130.00  178
 23  ω     91.00 178.00   0.50    0.30    --  106.40  61.00  30.00  174
 24  ω     89.00 178.00   0.50    0.30    --  106.40 134.00 -49.00  178
 25  ω    -92.00 -18.00   0.50    0.07    --  -46.54 134.00 -49.00  148
 26  ω    -85.00 -19.00   0.50    0.30    --  -91.75 125.00-180.00  132
 27  ω    -92.00 -19.00   0.50    0.30    --  -91.75 134.00 -49.00  146
 28  ω    -92.00 -18.00   0.50    0.07    --  -46.54 134.00 130.00  148
 29  ω    -92.00 -19.00   0.50    0.30    --  -91.75 134.00 130.00  146
 30  ω   -101.00 -19.00   0.50    0.30    --  -91.75  77.00 150.00  164
 31  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 150.00   64
 32  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00   0.00   64
 33  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -30.00   64
 34  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -60.00   64
 35  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00-180.00   64
 36  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00 -90.00   64
 37  ω   -101.00 -19.00   0.50    0.30    --  -91.75  77.00 -30.00  164
 38  ω    -51.00 -19.00   0.50    0.30    --  -91.75  45.00  90.00   64
 39  ω    -30.00  29.00   0.50    0.07    --  -46.54  19.00  90.00  118
 40  ω   -119.00 -32.00   0.50    0.07    --  -46.54 -42.00 -24.02  174
 41  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 150.00   70
 42  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 -30.00   70
 43  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00 -60.00   70
 44  ω   -118.00 -83.00   0.50    0.07    --  -46.54 -57.00-180.00   70
 45  ω   -166.00 -76.00   0.50    0.30    --  -91.75 -30.00-120.00  180
 46  ω   -118.00 -68.00   0.50    0.07    --  -46.54-134.00-116.00  100
 47  ω   -161.00 -68.00   0.50    0.30    --  -91.75-134.00-116.00  186
 48  ω   -164.00-101.00   0.50    0.30    --  -91.75 -77.00 -30.00  126
 49  ω   -118.00 -68.00   0.50    0.07    --  -46.54-134.00  63.00  100
 50  ω   -118.00 -88.00   0.50    0.07    --  -46.54-125.00   0.00   60
 51  ω   -161.00 -68.00   0.50    0.30    --  -91.75-134.00  63.00  186
 52  ω   -164.00 -91.00   0.50    0.30    --  -91.75 -61.00 150.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1052980000
_diffrn_orient_matrix_UB_12      0.0285234000
_diffrn_orient_matrix_UB_13      -0.0245260000
_diffrn_orient_matrix_UB_21      -0.0123279000
_diffrn_orient_matrix_UB_22      -0.2417718000
_diffrn_orient_matrix_UB_23      -0.0027209000
_diffrn_orient_matrix_UB_31      0.0213884000
_diffrn_orient_matrix_UB_32      0.0004321000
_diffrn_orient_matrix_UB_33      0.1038278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             2921
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.5133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0943
_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 Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C13(H13), C11(H11), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.41999(6) -0.01476(12) 0.19312(5) 0.02415(19) Uani 1 1 d . . . . .
O5 O 0.18008(6) -0.99421(13) 0.03397(5) 0.0269(2) Uani 1 1 d . . . . .
O2 O 0.42686(6) -0.18264(13) 0.32064(5) 0.0264(2) Uani 1 1 d . . . . .
N1 N 0.25341(7) -0.65632(15) 0.13385(6) 0.0201(2) Uani 1 1 d . . . . .
O4 O 0.17870(7) -0.84505(15) -0.09437(6) 0.0346(2) Uani 1 1 d . . . . .
O1 O 0.28056(6) -0.49435(12) 0.26946(5) 0.02312(19) Uani 1 1 d . . . . .
C2 C 0.34838(8) -0.34657(17) 0.17199(7) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.26236(8) -0.67871(17) 0.05245(7) 0.0201(2) Uani 1 1 d . . . . .
C14 C 0.20373(8) -0.84899(18) -0.01174(7) 0.0209(2) Uani 1 1 d . . . . .
C3 C 0.35827(8) -0.37214(18) 0.09105(7) 0.0215(2) Uani 1 1 d . . . . .
H3 H 0.394615 -0.271912 0.075765 0.026 Uiso 1 1 calc R U . . .
C4 C 0.31668(8) -0.54164(18) 0.02896(7) 0.0210(2) Uani 1 1 d . . . . .
C6 C 0.40055(8) -0.17583(17) 0.23776(7) 0.0206(2) Uani 1 1 d . . . . .
C8 C 0.33787(8) -0.56843(19) -0.05335(7) 0.0228(2) Uani 1 1 d . . . . .
C15 C 0.11441(9) -1.1554(2) -0.02144(8) 0.0307(3) Uani 1 1 d . . . . .
H15A H 0.147739 -1.266732 -0.039627 0.037 Uiso 1 1 calc R U . . .
H15B H 0.065751 -1.092425 -0.078280 0.037 Uiso 1 1 calc R U . . .
C9 C 0.38049(8) -0.7533(2) -0.06432(8) 0.0268(3) Uani 1 1 d . . . . .
H9 H 0.395125 -0.862859 -0.019585 0.032 Uiso 1 1 calc R U . . .
C13 C 0.31816(8) -0.4079(2) -0.11887(8) 0.0272(3) Uani 1 1 d . . . . .
H13 H 0.290247 -0.280189 -0.111448 0.033 Uiso 1 1 calc R U . . .
C7 C 0.47950(9) 0.14791(19) 0.25271(9) 0.0301(3) Uani 1 1 d . . . . .
H7A H 0.489392 0.258987 0.214781 0.045 Uiso 1 1 calc R U . . .
H7B H 0.540132 0.086521 0.293644 0.045 Uiso 1 1 calc R U . . .
H7C H 0.449333 0.208521 0.290126 0.045 Uiso 1 1 calc R U . . .
C11 C 0.38080(9) -0.6183(2) -0.20574(8) 0.0324(3) Uani 1 1 d . . . . .
H11 H 0.395120 -0.635784 -0.257786 0.039 Uiso 1 1 calc R U . . .
C10 C 0.40164(9) -0.7781(2) -0.14029(9) 0.0319(3) Uani 1 1 d . . . . .
H10 H 0.430437 -0.904667 -0.147498 0.038 Uiso 1 1 calc R U . . .
C1 C 0.29379(8) -0.49683(17) 0.19843(7) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.33916(9) -0.4337(2) -0.19510(8) 0.0313(3) Uani 1 1 d . . . . .
H12 H 0.324888 -0.324309 -0.239878 0.038 Uiso 1 1 calc R U . . .
C16 C 0.07041(11) -1.2467(2) 0.03857(9) 0.0419(4) Uani 1 1 d . . . . .
H16A H 0.018638 -1.340525 0.001313 0.063 Uiso 1 1 calc R U . . .
H16B H 0.046320 -1.131883 0.063901 0.063 Uiso 1 1 calc R U . . .
H16C H 0.117665 -1.326926 0.089507 0.063 Uiso 1 1 calc R U . . .
H1 H 0.2190(13) -0.757(3) 0.1506(12) 0.050 Uiso 1 1 d . 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
O3 C6 1.3482(13) . ?
O3 C7 1.4451(14) . ?
O5 C14 1.3177(13) . ?
O5 C15 1.4553(14) . ?
O2 C6 1.2050(13) . ?
N1 C5 1.3659(13) . ?
N1 C1 1.3892(14) . ?
N1 H1 0.941(19) . ?
O4 C14 1.2033(14) . ?
O1 C1 1.2305(13) . ?
C2 C3 1.3683(15) . ?
C2 C6 1.4881(15) . ?
C2 C1 1.4547(15) . ?
C5 C14 1.5042(15) . ?
C5 C4 1.3728(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.4183(16) . ?
C4 C8 1.4882(14) . ?
C8 C9 1.3946(17) . ?
C8 C13 1.3941(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5070(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3887(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.3918(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C10 1.388(2) . ?
C11 C12 1.384(2) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C6 O3 C7 114.86(9) . . ?
C14 O5 C15 116.55(9) . . ?
C5 N1 C1 125.41(9) . . ?
C5 N1 H1 119.8(11) . . ?
C1 N1 H1 114.7(11) . . ?
C3 C2 C6 120.06(10) . . ?
C3 C2 C1 120.43(10) . . ?
C1 C2 C6 119.28(9) . . ?
N1 C5 C14 116.14(9) . . ?
N1 C5 C4 120.90(10) . . ?
C4 C5 C14 122.77(9) . . ?
O5 C14 C5 111.07(9) . . ?
O4 C14 O5 125.29(11) . . ?
O4 C14 C5 123.56(10) . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 122.91(10) . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 116.49(10) . . ?
C5 C4 C8 124.02(10) . . ?
C3 C4 C8 119.40(10) . . ?
O3 C6 C2 111.02(9) . . ?
O2 C6 O3 123.57(10) . . ?
O2 C6 C2 125.30(10) . . ?
C9 C8 C4 120.05(10) . . ?
C13 C8 C4 120.82(11) . . ?
C13 C8 C9 119.10(10) . . ?
O5 C15 H15A 110.5 . . ?
O5 C15 H15B 110.5 . . ?
O5 C15 C16 106.35(10) . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.34(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.37(12) . . ?
C12 C13 H13 119.8 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 119.94(11) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.15(12) . . ?
C11 C10 H10 119.9 . . ?
N1 C1 C2 113.78(9) . . ?
O1 C1 N1 119.16(10) . . ?
O1 C1 C2 127.06(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.09(12) . . ?
C11 C12 H12 120.0 . . ?
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 . . ?

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
N1 C5 C14 O5 -22.76(13) . . . . ?
N1 C5 C14 O4 153.96(11) . . . . ?
N1 C5 C4 C3 -3.06(16) . . . . ?
N1 C5 C4 C8 173.40(10) . . . . ?
C2 C3 C4 C5 2.01(17) . . . . ?
C2 C3 C4 C8 -174.62(10) . . . . ?
C5 N1 C1 O1 -179.83(10) . . . . ?
C5 N1 C1 C2 0.51(15) . . . . ?
C5 C4 C8 C9 -56.87(16) . . . . ?
C5 C4 C8 C13 125.04(13) . . . . ?
C14 O5 C15 C16 -158.73(11) . . . . ?
C14 C5 C4 C3 171.90(10) . . . . ?
C14 C5 C4 C8 -11.64(17) . . . . ?
C3 C2 C6 O3 26.23(14) . . . . ?
C3 C2 C6 O2 -150.08(11) . . . . ?
C3 C2 C1 N1 -1.57(15) . . . . ?
C3 C2 C1 O1 178.81(11) . . . . ?
C3 C4 C8 C9 119.49(12) . . . . ?
C3 C4 C8 C13 -58.59(15) . . . . ?
C4 C5 C14 O5 162.06(10) . . . . ?
C4 C5 C14 O4 -21.22(17) . . . . ?
C4 C8 C9 C10 -179.10(11) . . . . ?
C4 C8 C13 C12 179.32(11) . . . . ?
C6 C2 C3 C4 174.77(10) . . . . ?
C6 C2 C1 N1 -176.05(9) . . . . ?
C6 C2 C1 O1 4.32(17) . . . . ?
C8 C9 C10 C11 0.26(18) . . . . ?
C8 C13 C12 C11 -0.73(18) . . . . ?
C15 O5 C14 O4 -3.42(17) . . . . ?
C15 O5 C14 C5 173.24(10) . . . . ?
C9 C8 C13 C12 1.21(17) . . . . ?
C13 C8 C9 C10 -0.98(17) . . . . ?
C7 O3 C6 O2 2.90(15) . . . . ?
C7 O3 C6 C2 -173.49(9) . . . . ?
C10 C11 C12 C13 0.01(19) . . . . ?
C1 N1 C5 C14 -173.39(10) . . . . ?
C1 N1 C5 C4 1.90(17) . . . . ?
C1 C2 C3 C4 0.33(17) . . . . ?
C1 C2 C6 O3 -159.27(9) . . . . ?
C1 C2 C6 O2 24.42(16) . . . . ?
C12 C11 C10 C9 0.23(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.826
