# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2022

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

data_ntpome
_database_code_depnum_ccdc_archive 'CCDC 2172044'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_audit_creation_date             2021-07-30
_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            NTPOMe
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H29 N3 O5'
_chemical_formula_sum            'C27 H29 N3 O5'
_chemical_formula_weight         475.53
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     @100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3717(2)
_cell_length_b                   15.2576(4)
_cell_length_c                   19.7373(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2521.09(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    99.99(14)
_cell_measurement_theta_max      67.3450
_cell_measurement_theta_min      3.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tubetype
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2693
_exptl_crystal_size_mid          0.2368
_exptl_crystal_size_min          0.2184
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13706
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.383
_diffrn_reflns_theta_min         3.662
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  59.00   0.50    4.82    --   41.33 -52.00 -30.00  168
  2  ω     25.00 106.00   0.50   19.27    --   96.67 -92.00-135.00  162
  3  ω     29.00  59.00   0.50   19.27    --   96.67 -52.00 -30.00   60
  4  ω     30.00  55.00   0.50   19.27    --   96.67 -50.00 -90.00   50
  5  ω     31.00  56.00   0.50   19.27    --   96.67 -50.00-120.00   50
  6  ω    -20.00  74.00   0.50    4.82    --   41.33 -92.00-135.00  188
  7  ω    -18.00  18.00   0.50    4.82    --   41.33 -11.00-150.00   72
  8  ω    -31.00  -5.00   0.50    4.82    --   41.33 -11.00 -60.00   52
  9  ω     30.00  55.00   0.50   19.27    --   96.67 -50.00  90.00   50
 10  ω     28.00 125.00   0.50   19.27    --   96.67 -82.00 116.00  194
 11  ω     84.00 157.00   0.50   19.27    --   96.67  33.00 150.00  146
 12  ω    105.00 167.00   0.50   19.27    --   96.67  96.00 150.00  124
 13  ω    142.00 170.00   0.50   19.27    --   96.67  96.00   0.00   56
 14  ω    106.00 135.00   0.50   19.27    --   96.67  96.00   0.00   58
 15  ω    101.00 168.00   0.50   19.27    --   96.67  92.00 -22.00  134
 16  ω     77.00 163.00   0.50   19.27    --   96.67  52.00 115.00  172
 17  ω     30.00  56.00   0.50   19.27    --   96.67 -50.00 150.00   52
 18  ω     30.00  55.00   0.50   19.27    --   96.67 -50.00 120.00   50
 19  ω     29.00  54.00   0.50   19.27    --   96.67 -59.00 120.00   50
 20  ω    -22.00  70.00   0.50    4.82    --   41.33 -82.00 116.00  184
 21  ω    -24.00  35.00   0.50    4.82    --  -41.33  11.00 -90.00  118
 22  ω    -70.00  28.00   0.50    4.82    --  -41.33  82.00-122.00  196
 23  ω    -59.00  26.00   0.50    4.82    --  -41.33  52.00 115.00  170
 24  ω    -59.00 -15.00   0.50   19.27    --  -82.50  52.00 115.00   88
 25  ω    -74.00  30.00   0.50    4.82    --  -41.33  92.00 -22.00  208
 26  ω    -80.00 -11.00   0.50   19.27    --  -82.50  92.00 -22.00  138
 27  ω   -109.00 -35.00   0.50    4.82    --  -41.33 -52.00 -30.00  148
 28  ω   -133.00-106.00   0.50   19.27    --  -82.50 -52.00 -30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321704000
_diffrn_orient_matrix_UB_12      0.0877187000
_diffrn_orient_matrix_UB_13      0.0359663000
_diffrn_orient_matrix_UB_21      0.1665338000
_diffrn_orient_matrix_UB_22      -0.0042246000
_diffrn_orient_matrix_UB_23      0.0330991000
_diffrn_orient_matrix_UB_31      0.0716833000
_diffrn_orient_matrix_UB_32      0.0497775000
_diffrn_orient_matrix_UB_33      -0.0608135000
_diffrn_oxdiff_digest_frames     
;
018b013ead58744a63357297487006cc91000259e29
;
_diffrn_oxdiff_digest_hkl        
;
011d77a1f7a06d2a6f929aeea1578ee00725fb
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.602
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3741
_reflns_number_total             4185
_reflns_odcompleteness_completeness 99.73
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1270 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.037
_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)+(0.1321P)²+0.9654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1897
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N19(H19), N16(H16), N10(H10), C6(H6), C5(H5), C3(H3), C29(H29), C2(H2),
 C35(H35), C31(H31), C25(H25), C28(H28), C27(H27), C34(H34), C32(H32), C26(H26),
  C33(H33)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O20 O 0.5967(4) 0.2378(2) 0.52848(15) 0.0331(8) Uani 1 1 d . . . . .
O15 O -0.0157(5) 0.4786(2) 0.64866(16) 0.0364(8) Uani 1 1 d . . . . .
O22 O 0.3674(4) 0.4762(2) 0.61535(16) 0.0344(8) Uani 1 1 d . . . . .
O13 O 0.0777(4) 0.6113(2) 0.61937(15) 0.0329(8) Uani 1 1 d . . . . .
O23 O 0.4294(5) -0.0353(2) 0.78428(17) 0.0380(8) Uani 1 1 d . . . . .
H23 H 0.4902 -0.0304 0.8166 0.057 Uiso 1 1 calc GR . . . .
N19 N 0.8990(5) 0.1947(3) 0.5844(2) 0.0340(9) Uani 1 1 d . . . . .
H19 H 0.9760 0.2061 0.5569 0.041 Uiso 1 1 calc R . . . .
N16 N 0.5343(5) 0.3137(3) 0.62293(19) 0.0289(9) Uani 1 1 d . . . . .
H16 H 0.5719 0.3405 0.6578 0.035 Uiso 1 1 calc R . . . .
N10 N 0.1861(5) 0.4144(2) 0.54613(19) 0.0281(8) Uani 1 1 d . . . . .
H10 H 0.1563 0.3691 0.5234 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3095(5) 0.4097(3) 0.5893(2) 0.0268(10) Uani 1 1 d . . . . .
C8 C 0.3628(6) 0.3191(3) 0.6108(2) 0.0276(10) Uani 1 1 d . . . . .
H8 H 0.3333 0.2768 0.5756 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6363(6) 0.2707(3) 0.5841(2) 0.0272(10) Uani 1 1 d . . . . .
C24 C -0.1390(6) 0.5691(3) 0.4866(2) 0.0307(10) Uani 1 1 d . . . . .
C11 C 0.1040(6) 0.4978(3) 0.5386(2) 0.0280(10) Uani 1 1 d . . . . .
H11 H 0.1767 0.5415 0.5193 0.034 Uiso 1 1 calc R . . . .
C6 C 0.2550(6) 0.1334(3) 0.6775(2) 0.0325(11) Uani 1 1 d . . . . .
H6 H 0.1872 0.1369 0.6403 0.039 Uiso 1 1 calc R . . . .
C30 C 0.8695(6) 0.1079(3) 0.6009(2) 0.0326(10) Uani 1 1 d . . . . .
C12 C 0.0489(6) 0.5270(3) 0.6087(2) 0.0288(10) Uani 1 1 d . . . . .
C1 C 0.3139(6) 0.2097(3) 0.7056(2) 0.0293(10) Uani 1 1 d . . . . .
C4 C 0.3940(6) 0.0454(3) 0.7594(2) 0.0317(10) Uani 1 1 d . . . . .
C5 C 0.2944(6) 0.0513(3) 0.7034(2) 0.0322(11) Uani 1 1 d . . . . .
H5 H 0.2542 0.0007 0.6833 0.039 Uiso 1 1 calc R . . . .
C3 C 0.4565(6) 0.1223(3) 0.7876(2) 0.0315(10) Uani 1 1 d . . . . .
H3 H 0.5259 0.1188 0.8243 0.038 Uiso 1 1 calc R . . . .
C18 C 0.8078(6) 0.2661(3) 0.6107(2) 0.0322(10) Uani 1 1 d . . . . .
H18A H 0.8618 0.3205 0.5995 0.039 Uiso 1 1 calc R . . . .
H18B H 0.8047 0.2615 0.6597 0.039 Uiso 1 1 calc R . . . .
C29 C -0.1141(6) 0.6270(3) 0.4322(2) 0.0346(11) Uani 1 1 d . . . . .
H29 H -0.0412 0.6129 0.3984 0.042 Uiso 1 1 calc R . . . .
C2 C 0.4165(6) 0.2025(3) 0.7618(2) 0.0320(10) Uani 1 1 d . . . . .
H2 H 0.4577 0.2529 0.7817 0.038 Uiso 1 1 calc R . . . .
C35 C 0.7594(6) 0.0839(3) 0.6497(3) 0.0341(11) Uani 1 1 d . . . . .
H35 H 0.6989 0.1266 0.6715 0.041 Uiso 1 1 calc R . . . .
C31 C 0.9578(6) 0.0419(3) 0.5695(3) 0.0371(11) Uani 1 1 d . . . . .
H31 H 1.0324 0.0568 0.5365 0.045 Uiso 1 1 calc R . . . .
C21 C -0.0435(7) 0.4867(3) 0.4924(2) 0.0329(11) Uani 1 1 d . . . . .
H21A H -0.0085 0.4689 0.4476 0.040 Uiso 1 1 calc R . . . .
H21B H -0.1108 0.4405 0.5104 0.040 Uiso 1 1 calc R . . . .
C7 C 0.2706(6) 0.2972(3) 0.6765(2) 0.0310(10) Uani 1 1 d . . . . .
H7A H 0.2922 0.3423 0.7099 0.037 Uiso 1 1 calc R . . . .
H7B H 0.1569 0.2981 0.6670 0.037 Uiso 1 1 calc R . . . .
C25 C -0.2479(7) 0.5931(4) 0.5364(3) 0.0419(13) Uani 1 1 d . . . . .
H25 H -0.2665 0.5552 0.5724 0.050 Uiso 1 1 calc R . . . .
C28 C -0.1976(7) 0.7045(3) 0.4291(3) 0.0387(12) Uani 1 1 d . . . . .
H28 H -0.1839 0.7413 0.3920 0.046 Uiso 1 1 calc R . . . .
C27 C -0.3025(7) 0.7287(4) 0.4806(3) 0.0413(13) Uani 1 1 d . . . . .
H27 H -0.3540 0.7827 0.4793 0.050 Uiso 1 1 calc R . . . .
C34 C 0.7386(7) -0.0053(4) 0.6666(3) 0.0430(13) Uani 1 1 d . . . . .
H34 H 0.6634 -0.0210 0.6991 0.052 Uiso 1 1 calc R . . . .
C32 C 0.9368(7) -0.0450(4) 0.5865(3) 0.0458(13) Uani 1 1 d . . . . .
H32 H 0.9961 -0.0883 0.5649 0.055 Uiso 1 1 calc R . . . .
C26 C -0.3287(8) 0.6712(4) 0.5337(3) 0.0473(14) Uani 1 1 d . . . . .
H26 H -0.4013 0.6856 0.5676 0.057 Uiso 1 1 calc R . . . .
C14 C 0.0172(8) 0.6462(4) 0.6828(3) 0.0451(14) Uani 1 1 d . . . . .
H14A H -0.0964 0.6379 0.6848 0.068 Uiso 1 1 calc GR . . . .
H14B H 0.0412 0.7076 0.6855 0.068 Uiso 1 1 calc GR . . . .
H14C H 0.0668 0.6161 0.7200 0.068 Uiso 1 1 calc GR . . . .
C33 C 0.8261(8) -0.0676(4) 0.6363(3) 0.0496(15) Uani 1 1 d . . . . .
H33 H 0.8129 -0.1260 0.6485 0.060 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O20 C17 1.251(5) . ?
O15 C12 1.209(6) . ?
O22 C9 1.236(6) . ?
O13 C12 1.325(6) . ?
O13 C14 1.451(6) . ?
O23 H23 0.8200 . ?
O23 C4 1.359(6) . ?
N19 H19 0.8600 . ?
N19 C30 1.385(7) . ?
N19 C18 1.429(7) . ?
N16 H16 0.8600 . ?
N16 C8 1.458(6) . ?
N16 C17 1.322(6) . ?
N10 H10 0.8600 . ?
N10 C9 1.341(6) . ?
N10 C11 1.454(6) . ?
C9 C8 1.514(6) . ?
C8 H8 0.9800 . ?
C8 C7 1.545(6) . ?
C17 C18 1.530(6) . ?
C24 C29 1.406(7) . ?
C24 C21 1.495(7) . ?
C24 C25 1.388(8) . ?
C11 H11 0.9800 . ?
C11 C12 1.525(6) . ?
C11 C21 1.545(7) . ?
C6 H6 0.9300 . ?
C6 C1 1.381(7) . ?
C6 C5 1.393(7) . ?
C30 C35 1.384(7) . ?
C30 C31 1.394(7) . ?
C1 C2 1.407(7) . ?
C1 C7 1.498(7) . ?
C4 C5 1.388(7) . ?
C4 C3 1.400(7) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.367(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C29 H29 0.9300 . ?
C29 C28 1.374(8) . ?
C2 H2 0.9300 . ?
C35 H35 0.9300 . ?
C35 C34 1.411(8) . ?
C31 H31 0.9300 . ?
C31 C32 1.380(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C26 1.372(8) . ?
C28 H28 0.9300 . ?
C28 C27 1.393(8) . ?
C27 H27 0.9300 . ?
C27 C26 1.384(8) . ?
C34 H34 0.9300 . ?
C34 C33 1.341(9) . ?
C32 H32 0.9300 . ?
C32 C33 1.394(9) . ?
C26 H26 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C33 H33 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
C12 O13 C14 115.5(4) . . ?
C4 O23 H23 109.5 . . ?
C30 N19 H19 118.4 . . ?
C30 N19 C18 123.3(4) . . ?
C18 N19 H19 118.4 . . ?
C8 N16 H16 117.7 . . ?
C17 N16 H16 117.7 . . ?
C17 N16 C8 124.7(4) . . ?
C9 N10 H10 120.8 . . ?
C9 N10 C11 118.4(4) . . ?
C11 N10 H10 120.8 . . ?
O22 C9 N10 121.5(4) . . ?
O22 C9 C8 121.2(4) . . ?
N10 C9 C8 117.0(4) . . ?
N16 C8 C9 112.8(4) . . ?
N16 C8 H8 109.1 . . ?
N16 C8 C7 110.1(4) . . ?
C9 C8 H8 109.1 . . ?
C9 C8 C7 106.6(4) . . ?
C7 C8 H8 109.1 . . ?
O20 C17 N16 122.5(4) . . ?
O20 C17 C18 122.1(4) . . ?
N16 C17 C18 115.4(4) . . ?
C29 C24 C21 120.5(5) . . ?
C25 C24 C29 118.2(5) . . ?
C25 C24 C21 121.3(4) . . ?
N10 C11 H11 110.0 . . ?
N10 C11 C12 107.8(4) . . ?
N10 C11 C21 110.0(4) . . ?
C12 C11 H11 110.0 . . ?
C12 C11 C21 109.0(4) . . ?
C21 C11 H11 110.0 . . ?
C1 C6 H6 119.1 . . ?
C1 C6 C5 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
N19 C30 C31 119.4(5) . . ?
C35 C30 N19 122.4(4) . . ?
C35 C30 C31 118.1(5) . . ?
O15 C12 O13 124.8(4) . . ?
O15 C12 C11 123.3(4) . . ?
O13 C12 C11 111.9(4) . . ?
C6 C1 C2 117.9(4) . . ?
C6 C1 C7 120.7(4) . . ?
C2 C1 C7 121.4(4) . . ?
O23 C4 C5 118.5(4) . . ?
O23 C4 C3 122.3(4) . . ?
C5 C4 C3 119.2(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5 120.3 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
N19 C18 C17 114.3(4) . . ?
N19 C18 H18A 108.7 . . ?
N19 C18 H18B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C24 C29 H29 120.0 . . ?
C28 C29 C24 119.9(5) . . ?
C28 C29 H29 120.0 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C30 C35 H35 119.9 . . ?
C30 C35 C34 120.1(5) . . ?
C34 C35 H35 119.9 . . ?
C30 C31 H31 119.4 . . ?
C32 C31 C30 121.2(5) . . ?
C32 C31 H31 119.4 . . ?
C24 C21 C11 112.3(4) . . ?
C24 C21 H21A 109.1 . . ?
C24 C21 H21B 109.1 . . ?
C11 C21 H21A 109.1 . . ?
C11 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C1 C7 C8 113.2(4) . . ?
C1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C24 C25 H25 119.2 . . ?
C26 C25 C24 121.7(5) . . ?
C26 C25 H25 119.2 . . ?
C29 C28 H28 119.5 . . ?
C29 C28 C27 121.1(5) . . ?
C27 C28 H28 119.5 . . ?
C28 C27 H27 120.5 . . ?
C26 C27 C28 118.9(5) . . ?
C26 C27 H27 120.5 . . ?
C35 C34 H34 119.7 . . ?
C33 C34 C35 120.7(5) . . ?
C33 C34 H34 119.7 . . ?
C31 C32 H32 120.2 . . ?
C31 C32 C33 119.6(5) . . ?
C33 C32 H32 120.2 . . ?
C25 C26 C27 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C34 C33 C32 120.1(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?

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
O20 C17 C18 N19 -24.7(6) . . . . ?
O22 C9 C8 N16 -39.5(6) . . . . ?
O22 C9 C8 C7 81.4(5) . . . . ?
O23 C4 C5 C6 179.2(5) . . . . ?
O23 C4 C3 C2 -179.1(5) . . . . ?
N19 C30 C35 C34 -177.4(5) . . . . ?
N19 C30 C31 C32 177.3(5) . . . . ?
N16 C8 C7 C1 -55.8(5) . . . . ?
N16 C17 C18 N19 157.1(4) . . . . ?
N10 C9 C8 N16 147.1(4) . . . . ?
N10 C9 C8 C7 -92.0(5) . . . . ?
N10 C11 C12 O15 -45.4(6) . . . . ?
N10 C11 C12 O13 135.8(4) . . . . ?
N10 C11 C21 C24 176.1(4) . . . . ?
C9 N10 C11 C12 -55.6(5) . . . . ?
C9 N10 C11 C21 -174.3(4) . . . . ?
C9 C8 C7 C1 -178.4(4) . . . . ?
C8 N16 C17 O20 8.0(7) . . . . ?
C8 N16 C17 C18 -173.9(4) . . . . ?
C17 N16 C8 C9 -110.2(5) . . . . ?
C17 N16 C8 C7 131.0(5) . . . . ?
C24 C29 C28 C27 2.7(8) . . . . ?
C24 C25 C26 C27 -0.2(9) . . . . ?
C11 N10 C9 O22 -9.8(7) . . . . ?
C11 N10 C9 C8 163.5(4) . . . . ?
C6 C1 C2 C3 0.0(7) . . . . ?
C6 C1 C7 C8 -77.0(6) . . . . ?
C30 N19 C18 C17 -69.4(6) . . . . ?
C30 C35 C34 C33 0.8(9) . . . . ?
C30 C31 C32 C33 -0.5(9) . . . . ?
C12 C11 C21 C24 58.0(5) . . . . ?
C1 C6 C5 C4 0.7(8) . . . . ?
C4 C3 C2 C1 -1.1(7) . . . . ?
C5 C6 C1 C2 0.2(7) . . . . ?
C5 C6 C1 C7 179.6(5) . . . . ?
C5 C4 C3 C2 1.9(7) . . . . ?
C3 C4 C5 C6 -1.7(7) . . . . ?
C18 N19 C30 C35 -6.8(8) . . . . ?
C18 N19 C30 C31 176.0(4) . . . . ?
C29 C24 C21 C11 95.1(5) . . . . ?
C29 C24 C25 C26 -0.7(8) . . . . ?
C29 C28 C27 C26 -3.6(8) . . . . ?
C2 C1 C7 C8 102.3(5) . . . . ?
C35 C30 C31 C32 -0.1(8) . . . . ?
C35 C34 C33 C32 -1.3(10) . . . . ?
C31 C30 C35 C34 -0.1(8) . . . . ?
C31 C32 C33 C34 1.2(10) . . . . ?
C21 C24 C29 C28 -177.1(5) . . . . ?
C21 C24 C25 C26 175.8(5) . . . . ?
C21 C11 C12 O15 74.0(6) . . . . ?
C21 C11 C12 O13 -104.8(4) . . . . ?
C7 C1 C2 C3 -179.4(4) . . . . ?
C25 C24 C29 C28 -0.6(7) . . . . ?
C25 C24 C21 C11 -81.3(6) . . . . ?
C28 C27 C26 C25 2.3(9) . . . . ?
C14 O13 C12 O15 -3.6(7) . . . . ?
C14 O13 C12 C11 175.2(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.298
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_npt_xylene_a
_database_code_depnum_ccdc_archive 'CCDC 2172045'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;IISER Kolkata
India
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_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         'C27 H29 N3 O5, H2 O'
_chemical_formula_sum            'C27 H27 N4 O5'
_chemical_formula_weight         493.55
_chemical_absolute_configuration unknown
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.9730(3)
_cell_length_b                   26.2917(17)
_cell_length_c                   9.3394(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.444(2)
_cell_angle_gamma                90
_cell_volume                     1221.08(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.8656.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             524.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35406
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.718
_diffrn_reflns_theta_min         2.314
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4381
_reflns_number_total             6335
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.063
_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)+(0.0696P)²+0.6105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1683
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C18(H18), C9(H9)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N1(H1), C16(H16), C13(H13), C5(H5), C15(H15), C14(H14),
 C2(H2A), C6(H6), C12(H12), C25(H25), C3(H3B), C4(H4), C21(H21), C24(H24),
 C22(H22)
2.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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
N2 N 0.7400(6) 0.52870(13) 0.5148(4) 0.0210(7) Uani 1 1 d . . . . .
H2 H 0.9086 0.5280 0.5441 0.025 Uiso 1 1 calc R . . . .
O1 O 0.3066(6) 0.53664(15) 0.5840(4) 0.0434(9) Uani 1 1 d . . . . .
N3 N 0.5512(6) 0.43211(14) 0.3087(4) 0.0247(8) Uani 1 1 d . . . . .
H3 H 0.3871 0.4445 0.3029 0.030 Uiso 1 1 calc R . . . .
O4 O 0.2743(8) 0.37819(19) 0.0933(4) 0.0561(12) Uani 1 1 d . . . . .
O2 O 0.9934(6) 0.45059(13) 0.3287(5) 0.0512(11) Uani 1 1 d . . . . .
O5 O 0.5713(10) 0.31516(13) 0.1172(4) 0.0544(11) Uani 1 1 d . . . . .
N1 N 0.4607(8) 0.57120(15) 0.8572(4) 0.0340(9) Uani 1 1 d . . . . .
H1 H 0.4190 0.5530 0.9330 0.041 Uiso 1 1 calc R . . . .
C8 C 0.5482(8) 0.53862(17) 0.6108(5) 0.0278(9) Uani 1 1 d . . . . .
C1 C 0.3334(9) 0.61753(17) 0.8351(5) 0.0271(9) Uani 1 1 d . . . . .
C18 C 0.5917(9) 0.37761(17) 0.2926(5) 0.0290(10) Uani 1 1 d . . . . .
H18 H 0.7888 0.3702 0.2904 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6822(8) 0.51909(16) 0.3644(5) 0.0244(9) Uani 1 1 d . . . . .
H9 H 0.4856 0.5241 0.3462 0.029 Uiso 1 1 calc R . . . .
C16 C 0.5536(9) 0.63192(18) 0.2176(5) 0.0300(10) Uani 1 1 d . . . . .
H16 H 0.4584 0.6117 0.1498 0.036 Uiso 1 1 calc R . . . .
O3 O 0.8150(11) 0.4208(3) 0.9627(5) 0.095(2) Uani 1 1 d . . . . .
H3A H 0.9704 0.4105 0.9837 0.143 Uiso 1 1 calc GR . . . .
C26 C 0.4619(10) 0.3585(2) 0.1556(5) 0.0368(11) Uani 1 1 d . . . . .
C11 C 0.7667(8) 0.61079(17) 0.2935(4) 0.0265(9) Uani 1 1 d . . . . .
C17 C 0.7563(8) 0.46384(18) 0.3319(5) 0.0289(10) Uani 1 1 d . . . . .
C13 C 0.8274(10) 0.6905(2) 0.4155(5) 0.0367(11) Uani 1 1 d . . . . .
H13 H 0.9220 0.7107 0.4837 0.044 Uiso 1 1 calc R . . . .
C20 C 0.5577(9) 0.3660(2) 0.5636(5) 0.0373(11) Uani 1 1 d . . . . .
C5 C -0.0065(9) 0.6775(2) 0.9088(5) 0.0344(11) Uani 1 1 d . . . . .
H5 H -0.1521 0.6861 0.9694 0.041 Uiso 1 1 calc R . . . .
C10 C 0.8411(9) 0.55544(18) 0.2693(5) 0.0306(10) Uani 1 1 d . . . . .
H10A H 1.0356 0.5509 0.2888 0.037 Uiso 1 1 calc R . . . .
H10B H 0.8074 0.5467 0.1677 0.037 Uiso 1 1 calc R . . . .
C15 C 0.4774(10) 0.68189(18) 0.2390(5) 0.0343(11) Uani 1 1 d . . . . .
H15 H 0.3315 0.6958 0.1857 0.041 Uiso 1 1 calc R . . . .
C14 C 0.6129(10) 0.71159(19) 0.3377(5) 0.0361(11) Uani 1 1 d . . . . .
H14 H 0.5612 0.7459 0.3528 0.043 Uiso 1 1 calc R . . . .
C7 C 0.6595(8) 0.55205(19) 0.7595(5) 0.0315(10) Uani 1 1 d . . . . .
H7A H 0.7432 0.5213 0.8017 0.038 Uiso 1 1 calc R . . . .
H7B H 0.8024 0.5780 0.7486 0.038 Uiso 1 1 calc R . . . .
C2 C 0.4173(10) 0.6518(2) 0.7310(5) 0.0345(11) Uani 1 1 d . . . . .
H2A H 0.5612 0.6432 0.6693 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1180(8) 0.63126(18) 0.9231(5) 0.0280(9) Uani 1 1 d . . . . .
H6 H 0.0574 0.6081 0.9939 0.034 Uiso 1 1 calc R . . . .
C12 C 0.9020(9) 0.64054(18) 0.3931(5) 0.0318(10) Uani 1 1 d . . . . .
H12 H 1.0472 0.6264 0.4465 0.038 Uiso 1 1 calc R . . . .
C25 C 0.4277(11) 0.4052(2) 0.6329(5) 0.0406(12) Uani 1 1 d . . . . .
H25 H 0.2758 0.4209 0.5892 0.049 Uiso 1 1 calc R . . . .
C3 C 0.2898(10) 0.6988(2) 0.7176(5) 0.0385(12) Uani 1 1 d . . . . .
H3B H 0.3484 0.7222 0.6467 0.046 Uiso 1 1 calc R . . . .
C19 C 0.4632(10) 0.34840(19) 0.4178(5) 0.0336(10) Uani 1 1 d . . . . .
H19A H 0.2654 0.3523 0.4117 0.040 Uiso 1 1 calc R . . . .
H19B H 0.5048 0.3118 0.4075 0.040 Uiso 1 1 calc R . . . .
C4 C 0.0801(10) 0.7118(2) 0.8055(6) 0.0412(12) Uani 1 1 d . . . . .
H4 H -0.0049 0.7440 0.7959 0.049 Uiso 1 1 calc R . . . .
C21 C 0.7801(11) 0.3446(3) 0.6332(6) 0.0540(16) Uani 1 1 d . . . . .
H21 H 0.8743 0.3174 0.5893 0.065 Uiso 1 1 calc R . . . .
C24 C 0.5179(14) 0.4221(3) 0.7672(6) 0.0562(18) Uani 1 1 d . . . . .
H24 H 0.4241 0.4486 0.8145 0.067 Uiso 1 1 calc R . . . .
C27 C 0.4443(19) 0.2890(2) -0.0040(7) 0.073(2) Uani 1 1 d . . . . .
H27A H 0.4796 0.3080 -0.0923 0.109 Uiso 1 1 calc GR . . . .
H27B H 0.2498 0.2870 0.0113 0.109 Uiso 1 1 calc GR . . . .
H27C H 0.5183 0.2546 -0.0122 0.109 Uiso 1 1 calc GR . . . .
C23 C 0.7383(14) 0.4010(3) 0.8309(6) 0.068(2) Uani 1 1 d . . . . .
C22 C 0.8653(13) 0.3627(4) 0.7661(7) 0.075(3) Uani 1 1 d . . . . .
H22 H 1.0167 0.3475 0.8117 0.090 Uiso 1 1 calc R . . . .
O6 O 0.279(3) 0.4931(3) 1.0505(9) 0.184(5) Uani 1 1 d . . . . .
H6A H 0.1878 0.4844 1.1258 0.276 Uiso 1 1 d G . . . .
H6B H 0.3749 0.4664 1.0306 0.276 Uiso 1 1 d G . . . .


_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
N2 H2 0.8800 . ?
N2 C8 1.340(5) . ?
N2 C9 1.453(5) . ?
O1 C8 1.227(5) . ?
N3 H3 0.8800 . ?
N3 C18 1.455(6) . ?
N3 C17 1.334(5) . ?
O4 C26 1.212(7) . ?
O2 C17 1.230(5) . ?
O5 C26 1.314(7) . ?
O5 C27 1.463(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.387(6) . ?
N1 C7 1.442(6) . ?
C8 C7 1.532(6) . ?
C1 C2 1.392(7) . ?
C1 C6 1.403(6) . ?
C18 H18 1.0000 . ?
C18 C26 1.514(7) . ?
C18 C19 1.542(7) . ?
C9 H9 1.0000 . ?
C9 C17 1.530(6) . ?
C9 C10 1.529(7) . ?
C16 H16 0.9500 . ?
C16 C11 1.386(6) . ?
C16 C15 1.382(7) . ?
O3 H3A 0.8400 . ?
O3 C23 1.387(8) . ?
C11 C10 1.519(6) . ?
C11 C12 1.386(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.400(7) . ?
C13 C12 1.382(7) . ?
C20 C25 1.380(8) . ?
C20 C19 1.510(7) . ?
C20 C21 1.397(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(7) . ?
C5 C4 1.392(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C14 1.380(7) . ?
C14 H14 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2A 0.9500 . ?
C2 C3 1.394(8) . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.401(8) . ?
C3 H3B 0.9500 . ?
C3 C4 1.375(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C4 H4 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.393(10) . ?
C24 H24 0.9500 . ?
C24 C23 1.362(11) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C23 C22 1.336(12) . ?
C22 H22 0.9500 . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8701 . ?

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
C8 N2 H2 118.5 . . ?
C8 N2 C9 123.0(3) . . ?
C9 N2 H2 118.5 . . ?
C18 N3 H3 119.1 . . ?
C17 N3 H3 119.1 . . ?
C17 N3 C18 121.8(4) . . ?
C26 O5 C27 116.2(5) . . ?
C1 N1 H1 119.1 . . ?
C1 N1 C7 121.8(4) . . ?
C7 N1 H1 119.1 . . ?
N2 C8 C7 113.4(3) . . ?
O1 C8 N2 123.8(4) . . ?
O1 C8 C7 122.7(4) . . ?
N1 C1 C2 122.3(4) . . ?
N1 C1 C6 119.2(4) . . ?
C2 C1 C6 118.5(4) . . ?
N3 C18 H18 109.3 . . ?
N3 C18 C26 110.9(4) . . ?
N3 C18 C19 110.7(4) . . ?
C26 C18 H18 109.3 . . ?
C26 C18 C19 107.4(3) . . ?
C19 C18 H18 109.3 . . ?
N2 C9 H9 109.1 . . ?
N2 C9 C17 108.1(3) . . ?
N2 C9 C10 110.7(3) . . ?
C17 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C10 C9 C17 110.6(3) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C11 121.1(4) . . ?
C23 O3 H3A 109.5 . . ?
O4 C26 O5 123.9(5) . . ?
O4 C26 C18 125.8(5) . . ?
O5 C26 C18 110.1(5) . . ?
C16 C11 C10 119.6(4) . . ?
C12 C11 C16 118.8(4) . . ?
C12 C11 C10 121.5(4) . . ?
N3 C17 C9 116.2(3) . . ?
O2 C17 N3 123.4(4) . . ?
O2 C17 C9 120.4(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(5) . . ?
C25 C20 C19 120.5(5) . . ?
C25 C20 C21 117.1(5) . . ?
C21 C20 C19 122.4(5) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.1(5) . . ?
C4 C5 H5 120.0 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.4 . . ?
N1 C7 C8 114.2(4) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(4) . . ?
C5 C6 H6 119.4 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C20 C25 H25 119.7 . . ?
C20 C25 C24 120.6(6) . . ?
C24 C25 H25 119.7 . . ?
C2 C3 H3B 119.6 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3B 119.6 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 C18 113.8(4) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.6 . . ?
C25 C24 H24 119.6 . . ?
C23 C24 C25 120.9(7) . . ?
C23 C24 H24 119.6 . . ?
O5 C27 H27A 109.5 . . ?
O5 C27 H27B 109.5 . . ?
O5 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C23 O3 116.7(8) . . ?
C22 C23 O3 123.9(8) . . ?
C22 C23 C24 119.4(6) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.3(7) . . ?
C23 C22 H22 119.3 . . ?
H6A O6 H6B 104.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
