# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_balaibtyr
_database_code_depnum_ccdc_archive 'CCDC 2106153'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2021-06-22
_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         'C22 H33 N3 O7'
_chemical_formula_sum            'C22 H33 N3 O7'
_chemical_formula_weight         451.51
_chemical_absolute_configuration s
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9599(4)
_cell_length_b                   19.6632(13)
_cell_length_c                   20.5253(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2405.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.0530
_cell_measurement_theta_min      3.0930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6038
_diffrn_reflns_point_group_measured_fraction_full 0.844
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        66.140
_diffrn_reflns_theta_max         66.140
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   79.00  169.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega   93.00  140.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  123.00  155.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  128.00  156.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  104.00  131.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  178.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  151.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega  126.00  153.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega  153.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  152.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega  101.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  136.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega   29.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00  102.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 14 omega   26.00   85.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -146.0000 59

#__ type_ start__ end____ width___ exp.time_
 15 omega   15.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406  -45.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
 16 omega   45.00   87.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       67.0406   61.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 17 omega  -14.00   12.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  104.0000  -45.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  -16.00   39.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   77.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega  -49.00  -22.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  -77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega  -16.00   38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  -77.0000   30.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0261570000
_diffrn_orient_matrix_UB_12      0.0767088000
_diffrn_orient_matrix_UB_13      0.0135395000
_diffrn_orient_matrix_UB_21      -0.2475715000
_diffrn_orient_matrix_UB_22      -0.0037268000
_diffrn_orient_matrix_UB_23      -0.0212557000
_diffrn_orient_matrix_UB_31      -0.0692239000
_diffrn_orient_matrix_UB_32      -0.0157681000
_diffrn_orient_matrix_UB_33      0.0706744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.639
_reflns_Friedel_fraction_max     0.639
_reflns_number_gt                2846
_reflns_number_total             3551
_reflns_odcompleteness_completeness 97.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.035
_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)+(0.1040P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1787
_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:
 C14(H14), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), N15(H15), C2(H2), N9(H9), N12(H12), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C19(H19A,H19B,
 H19C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O22 O -0.1208(7) -0.03930(17) -0.67457(13) 0.0316(9) Uani 1 1 d . . . . .
O32 O -1.1789(7) 0.10590(18) -0.96192(14) 0.0329(9) Uani 1 1 d . . . . .
H32 H -1.1351 0.1120 -0.9993 0.049 Uiso 1 1 calc GR . . . .
O29 O -0.9856(6) -0.16110(18) -0.84469(15) 0.0304(8) Uani 1 1 d . . . . .
O24 O -0.3729(6) -0.15764(17) -0.59232(14) 0.0293(8) Uani 1 1 d . . . . .
O17 O -0.1760(7) 0.02508(16) -0.58311(14) 0.0314(9) Uani 1 1 d . . . . .
O27 O -0.7461(6) -0.24024(17) -0.72636(14) 0.0274(8) Uani 1 1 d . . . . .
O31 O -0.6450(7) -0.20003(18) -0.87404(15) 0.0354(9) Uani 1 1 d . . . . .
C3 C -0.8544(10) 0.0314(2) -0.9598(2) 0.0289(12) Uani 1 1 d . . . . .
H3 H -0.8358 0.0353 -1.0046 0.035 Uiso 1 1 calc R . . . .
N15 N -0.0022(8) -0.07414(19) -0.57456(17) 0.0263(10) Uani 1 1 d . . . . .
H15 H 0.0415 -0.0614 -0.5365 0.032 Uiso 1 1 calc R . . . .
C28 C -0.7618(9) -0.1656(3) -0.8396(2) 0.0286(12) Uani 1 1 d . . . . .
C10 C -0.5527(9) -0.2161(2) -0.72169(19) 0.0230(11) Uani 1 1 d . . . . .
C2 C -0.7070(9) -0.0076(2) -0.9245(2) 0.0274(11) Uani 1 1 d . . . . .
H2 H -0.5914 -0.0299 -0.9461 0.033 Uiso 1 1 calc R . . . .
N9 N -0.5032(8) -0.1559(2) -0.74808(17) 0.0288(10) Uani 1 1 d . . . . .
H9 H -0.3715 -0.1388 -0.7430 0.035 Uiso 1 1 calc R . . . .
N12 N -0.1803(7) -0.21541(19) -0.67034(15) 0.0226(9) Uani 1 1 d . . . . .
H12 H -0.0546 -0.2177 -0.6908 0.027 Uiso 1 1 calc R . . . .
C1 C -0.7256(9) -0.0146(2) -0.8568(2) 0.0260(11) Uani 1 1 d . . . . .
C5 C -1.0557(10) 0.0572(3) -0.8623(2) 0.0329(12) Uani 1 1 d . . . . .
H5 H -1.1725 0.0791 -0.8409 0.039 Uiso 1 1 calc R . . . .
C14 C 0.0299(9) -0.1434(2) -0.5964(2) 0.0250(11) Uani 1 1 d . . . . .
H14 H 0.1391 -0.1444 -0.6321 0.030 Uiso 1 1 calc R . . . .
C13 C -0.1952(9) -0.1723(2) -0.61986(19) 0.0227(10) Uani 1 1 d . . . . .
C16 C -0.1038(9) -0.0295(2) -0.6161(2) 0.0258(11) Uani 1 1 d . . . . .
C25 C -0.4502(10) -0.3045(2) -0.6385(2) 0.0306(12) Uani 1 1 d . . . . .
H25A H -0.5057 -0.2772 -0.6033 0.046 Uiso 1 1 calc GR . . . .
H25B H -0.3306 -0.3330 -0.6230 0.046 Uiso 1 1 calc GR . . . .
H25C H -0.5692 -0.3324 -0.6552 0.046 Uiso 1 1 calc GR . . . .
C26 C -0.2710(9) -0.3025(2) -0.7483(2) 0.0279(11) Uani 1 1 d . . . . .
H26A H -0.3881 -0.3315 -0.7644 0.042 Uiso 1 1 calc GR . . . .
H26B H -0.1491 -0.3298 -0.7325 0.042 Uiso 1 1 calc GR . . . .
H26C H -0.2185 -0.2737 -0.7829 0.042 Uiso 1 1 calc GR . . . .
C30 C -1.0798(10) -0.2001(3) -0.8980(2) 0.0383(14) Uani 1 1 d . . . . .
H30A H -1.0199 -0.1839 -0.9385 0.057 Uiso 1 1 calc GR . . . .
H30B H -1.2400 -0.1952 -0.8981 0.057 Uiso 1 1 calc GR . . . .
H30C H -1.0418 -0.2472 -0.8926 0.057 Uiso 1 1 calc GR . . . .
C7 C -0.5636(10) -0.0566(2) -0.8178(2) 0.0319(12) Uani 1 1 d . . . . .
H7A H -0.4976 -0.0283 -0.7842 0.038 Uiso 1 1 calc R . . . .
H7B H -0.4435 -0.0718 -0.8462 0.038 Uiso 1 1 calc R . . . .
C8 C -0.6725(10) -0.1189(2) -0.7856(2) 0.0281(11) Uani 1 1 d . . . . .
H8 H -0.7956 -0.1045 -0.7571 0.034 Uiso 1 1 calc R . . . .
C19 C -0.5255(10) 0.0467(3) -0.6415(3) 0.0414(14) Uani 1 1 d . . . . .
H19A H -0.4899 0.0158 -0.6762 0.062 Uiso 1 1 calc GR . . . .
H19B H -0.6222 0.0820 -0.6576 0.062 Uiso 1 1 calc GR . . . .
H19C H -0.6001 0.0225 -0.6071 0.062 Uiso 1 1 calc GR . . . .
C4 C -1.0305(9) 0.0650(2) -0.9297(2) 0.0250(11) Uani 1 1 d . . . . .
C11 C -0.3625(9) -0.2583(2) -0.69270(19) 0.0244(11) Uani 1 1 d . . . . .
C6 C -0.9099(10) 0.0175(3) -0.8277(2) 0.0331(13) Uani 1 1 d . . . . .
H6 H -0.9339 0.0116 -0.7833 0.040 Uiso 1 1 calc R . . . .
C23 C 0.1132(10) -0.1879(3) -0.5400(2) 0.0295(12) Uani 1 1 d . . . . .
H23A H 0.2565 -0.1716 -0.5255 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.1274 -0.2341 -0.5546 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.0077 -0.1858 -0.5047 0.044 Uiso 1 1 calc GR . . . .
C20 C -0.1712(11) 0.1130(3) -0.6676(2) 0.0405(14) Uani 1 1 d . . . . .
H20A H -0.0280 0.1249 -0.6496 0.061 Uiso 1 1 calc GR . . . .
H20B H -0.2465 0.1534 -0.6822 0.061 Uiso 1 1 calc GR . . . .
H20C H -0.1500 0.0827 -0.7038 0.061 Uiso 1 1 calc GR . . . .
C18 C -0.3131(10) 0.0778(2) -0.6157(2) 0.0324(12) Uani 1 1 d . . . . .
C21 C -0.3617(13) 0.1262(3) -0.5598(3) 0.0464(16) Uani 1 1 d . . . . .
H21A H -0.4379 0.1021 -0.5256 0.070 Uiso 1 1 calc GR . . . .
H21B H -0.4548 0.1627 -0.5750 0.070 Uiso 1 1 calc GR . . . .
H21C H -0.2232 0.1443 -0.5434 0.070 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O22 C16 1.220(5) . ?
O32 C4 1.366(6) . ?
O29 C28 1.341(7) . ?
O29 C30 1.449(6) . ?
O24 C13 1.235(6) . ?
O17 C16 1.341(6) . ?
O17 C18 1.480(6) . ?
O27 C10 1.250(6) . ?
O31 C28 1.201(6) . ?
C3 C2 1.373(7) . ?
C3 C4 1.385(7) . ?
N15 C14 1.447(6) . ?
N15 C16 1.365(6) . ?
C28 C8 1.535(7) . ?
C10 N9 1.335(6) . ?
C10 C11 1.526(7) . ?
C2 C1 1.401(6) . ?
N9 C8 1.463(6) . ?
N12 C13 1.342(5) . ?
N12 C11 1.450(6) . ?
C1 C7 1.501(7) . ?
C1 C6 1.401(7) . ?
C5 C4 1.401(6) . ?
C5 C6 1.366(7) . ?
C14 C13 1.535(7) . ?
C14 C23 1.532(6) . ?
C25 C11 1.528(6) . ?
C26 C11 1.535(6) . ?
C7 C8 1.535(7) . ?
C19 C18 1.502(9) . ?
C20 C18 1.526(7) . ?
C18 C21 1.518(7) . ?

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
C28 O29 C30 114.1(4) . . ?
C16 O17 C18 120.7(3) . . ?
C2 C3 C4 121.0(4) . . ?
C16 N15 C14 118.1(4) . . ?
O29 C28 C8 111.2(5) . . ?
O31 C28 O29 124.6(5) . . ?
O31 C28 C8 124.2(5) . . ?
O27 C10 N9 120.6(5) . . ?
O27 C10 C11 120.5(4) . . ?
N9 C10 C11 118.5(5) . . ?
C3 C2 C1 121.9(5) . . ?
C10 N9 C8 120.1(5) . . ?
C13 N12 C11 124.3(4) . . ?
C2 C1 C7 122.2(5) . . ?
C6 C1 C2 116.1(4) . . ?
C6 C1 C7 121.7(4) . . ?
C6 C5 C4 120.5(5) . . ?
N15 C14 C13 109.3(4) . . ?
N15 C14 C23 110.3(3) . . ?
C23 C14 C13 108.0(4) . . ?
O24 C13 N12 123.9(5) . . ?
O24 C13 C14 121.3(4) . . ?
N12 C13 C14 114.8(4) . . ?
O22 C16 O17 126.6(4) . . ?
O22 C16 N15 123.4(5) . . ?
O17 C16 N15 110.0(3) . . ?
C1 C7 C8 113.3(5) . . ?
N9 C8 C28 108.8(4) . . ?
N9 C8 C7 109.4(4) . . ?
C7 C8 C28 108.3(4) . . ?
O32 C4 C3 123.7(4) . . ?
O32 C4 C5 118.3(5) . . ?
C3 C4 C5 118.0(4) . . ?
C10 C11 C25 110.7(4) . . ?
C10 C11 C26 106.3(3) . . ?
N12 C11 C10 111.3(4) . . ?
N12 C11 C25 111.8(4) . . ?
N12 C11 C26 107.4(4) . . ?
C25 C11 C26 109.1(4) . . ?
C5 C6 C1 122.3(4) . . ?
O17 C18 C19 109.8(4) . . ?
O17 C18 C20 109.1(5) . . ?
O17 C18 C21 101.7(4) . . ?
C19 C18 C20 113.9(4) . . ?
C19 C18 C21 111.1(5) . . ?
C21 C18 C20 110.5(4) . . ?

_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 0.166 0.158 0.485 17.9 0.3 ?
2 -0.166 0.658 0.015 17.9 0.3 ?
3 0.334 0.842 0.985 17.9 0.3 ?
4 0.666 0.342 0.515 17.9 0.3 ?


_olex2_date_sample_data_collection 2015-11-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_khbaapome
_database_code_depnum_ccdc_archive 'CCDC 2106154'
loop_
_audit_author_name
_audit_author_address
'Debasish Haldar'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_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         'C22 H33 N3 O6 [+ solvent]'
_chemical_formula_sum            'C22 H33 N3 O6 [+ solvent]'
_chemical_formula_weight         435.51
_chemical_absolute_configuration s
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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                   5.88570(10)
_cell_length_b                   18.9299(5)
_cell_length_c                   21.3905(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2383.24(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10138
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      66.1460
_cell_measurement_theta_min      3.1010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2759
_exptl_crystal_size_mid          0.2345
_exptl_crystal_size_min          0.1986
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20483
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.328
_diffrn_reflns_theta_max         66.328
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   57.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  178.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega   57.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  178.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000   30.0000 114

#__ type_ start__ end____ width___ exp.time_
  4 omega   57.00  150.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656  178.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656  -61.0000   30.0000 113

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656  -45.0000 -150.0000 127

#__ type_ start__ end____ width___ exp.time_
  7 omega   28.00  158.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000   30.0000 130

#__ type_ start__ end____ width___ exp.time_
  8 omega   69.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -120.0000 109

#__ type_ start__ end____ width___ exp.time_
  9 omega   28.00  158.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000   30.0000 130

#__ type_ start__ end____ width___ exp.time_
 10 omega   19.00  158.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000 -120.0000 139

#__ type_ start__ end____ width___ exp.time_
 11 omega  101.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 12 omega   71.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   96.9420 107

#__ type_ start__ end____ width___ exp.time_
 13 omega   71.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  -30.0000 107

#__ type_ start__ end____ width___ exp.time_
 14 omega  101.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 15 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000 -180.0000 128

#__ type_ start__ end____ width___ exp.time_
 16 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000  -90.0000 128

#__ type_ start__ end____ width___ exp.time_
 17 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000  120.0000 114

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  147.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656   45.0000 -180.0000 127

#__ type_ start__ end____ width___ exp.time_
 19 omega   30.00  144.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000   60.0000 114

#__ type_ start__ end____ width___ exp.time_
 20 omega   20.00  147.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1656   45.0000  -30.0000 127

#__ type_ start__ end____ width___ exp.time_
 21 omega   69.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
 22 omega   86.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
 23 omega   71.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000   60.0000 107

#__ type_ start__ end____ width___ exp.time_
 24 omega   21.00  113.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
 25 omega   65.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000  123.0000 113

#__ type_ start__ end____ width___ exp.time_
 26 omega   65.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 27 omega   69.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -150.0000 109

#__ type_ start__ end____ width___ exp.time_
 28 omega   65.00  166.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega   69.00  178.00   1.0000   15.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000   30.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0102971000
_diffrn_orient_matrix_UB_12      0.0342606000
_diffrn_orient_matrix_UB_13      0.0652895000
_diffrn_orient_matrix_UB_21      -0.1575044000
_diffrn_orient_matrix_UB_22      0.0581425000
_diffrn_orient_matrix_UB_23      -0.0257300000
_diffrn_orient_matrix_UB_31      -0.2086068000
_diffrn_orient_matrix_UB_32      -0.0455525000
_diffrn_orient_matrix_UB_33      0.0162376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3995
_reflns_number_total             4152
_reflns_odcompleteness_completeness 98.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.247
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.053
_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)+(0.0894P)²+0.2541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1399
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N3(H3), C19(H19), C18(H18), C22(H22), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C15(H15A,H15B,
 H15C), C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C)
;
_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
O3 O 0.3647(4) 0.37492(11) 0.18843(11) 0.0281(5) Uani 1 1 d . . . . .
O1 O 0.5416(4) 0.30919(11) 0.35389(11) 0.0280(5) Uani 1 1 d . . . . .
O4 O 0.0136(4) 0.53942(11) 0.15722(11) 0.0266(5) Uani 1 1 d . . . . .
O6 O -0.2304(4) 0.62582(11) 0.26988(12) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.5644(4) 0.42216(11) 0.31596(11) 0.0288(5) Uani 1 1 d . . . . .
O5 O 0.1061(4) 0.67450(11) 0.24488(11) 0.0295(5) Uani 1 1 d . . . . .
N2 N 0.5801(4) 0.46896(12) 0.15918(12) 0.0227(5) Uani 1 1 d . . . . .
H2 H 0.7130 0.4878 0.1605 0.027 Uiso 1 1 calc R . . . .
N1 N 0.7196(4) 0.32905(13) 0.26499(13) 0.0255(6) Uani 1 1 d . . . . .
H1 H 0.7643 0.2859 0.2680 0.031 Uiso 1 1 calc R . . . .
N3 N 0.2626(4) 0.53106(14) 0.23618(13) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.3987 0.5216 0.2482 0.030 Uiso 1 1 calc R . . . .
C8 C 0.5501(5) 0.40450(15) 0.18520(14) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.2061(5) 0.52521(15) 0.17594(15) 0.0234(6) Uani 1 1 d . . . . .
C5 C 0.6048(5) 0.35911(16) 0.31208(15) 0.0254(6) Uani 1 1 d . . . . .
C17 C 0.0398(5) 0.58663(16) 0.39491(15) 0.0250(6) Uani 1 1 d . . . . .
C13 C 0.0930(5) 0.55350(15) 0.28130(15) 0.0242(6) Uani 1 1 d . . . . .
H13 H -0.0287 0.5182 0.2834 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2040(5) 0.56114(16) 0.34585(16) 0.0271(7) Uani 1 1 d . . . . .
H16A H 0.2653 0.5158 0.3586 0.033 Uiso 1 1 calc R . . . .
H16B H 0.3295 0.5942 0.3429 0.033 Uiso 1 1 calc R . . . .
C14 C -0.0061(5) 0.62456(16) 0.26203(15) 0.0229(6) Uani 1 1 d . . . . .
C6 C 0.7689(5) 0.36967(15) 0.20850(15) 0.0242(6) Uani 1 1 d . . . . .
H6 H 0.8824 0.4060 0.2178 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8582(6) 0.32079(16) 0.15823(15) 0.0283(7) Uani 1 1 d . . . . .
H7A H 0.9924 0.2974 0.1731 0.042 Uiso 1 1 calc GR . . . .
H7B H 0.8944 0.3477 0.1215 0.042 Uiso 1 1 calc GR . . . .
H7C H 0.7445 0.2863 0.1482 0.042 Uiso 1 1 calc GR . . . .
C11 C 0.3007(5) 0.46767(17) 0.07291(16) 0.0284(7) Uani 1 1 d . . . . .
H11A H 0.4184 0.4609 0.0424 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.1789 0.4944 0.0547 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.2446 0.4225 0.0864 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.3964(5) 0.50773(15) 0.12895(15) 0.0248(6) Uani 1 1 d . . . . .
C19 C -0.3127(6) 0.5736(2) 0.45122(16) 0.0336(7) Uani 1 1 d . . . . .
H19 H -0.4430 0.5476 0.4599 0.040 Uiso 1 1 calc R . . . .
C4 C 0.3821(6) 0.32580(17) 0.40425(17) 0.0319(7) Uani 1 1 d . . . . .
C18 C -0.1574(6) 0.54873(18) 0.40850(16) 0.0298(7) Uani 1 1 d . . . . .
H18 H -0.1842 0.5060 0.3884 0.036 Uiso 1 1 calc R . . . .
C10 C 0.4936(5) 0.57937(17) 0.10786(16) 0.0298(7) Uani 1 1 d . . . . .
H10A H 0.5567 0.6036 0.1433 0.045 Uiso 1 1 calc GR . . . .
H10B H 0.3745 0.6075 0.0899 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.6103 0.5717 0.0772 0.045 Uiso 1 1 calc GR . . . .
C15 C -0.3382(6) 0.69367(18) 0.2595(2) 0.0374(8) Uani 1 1 d . . . . .
H15A H -0.2805 0.7142 0.2217 0.056 Uiso 1 1 calc GR . . . .
H15B H -0.3059 0.7244 0.2941 0.056 Uiso 1 1 calc GR . . . .
H15C H -0.4995 0.6873 0.2559 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.0771(6) 0.65018(17) 0.42671(17) 0.0333(7) Uani 1 1 d . . . . .
H22 H 0.2088 0.6759 0.4190 0.040 Uiso 1 1 calc R . . . .
C20 C -0.2747(7) 0.63776(18) 0.48160(17) 0.0361(8) Uani 1 1 d . . . . .
H20 H -0.3808 0.6551 0.5099 0.043 Uiso 1 1 calc R . . . .
C21 C -0.0795(7) 0.67504(18) 0.46931(18) 0.0398(9) Uani 1 1 d . . . . .
H21 H -0.0527 0.7175 0.4899 0.048 Uiso 1 1 calc R . . . .
C2 C 0.4894(8) 0.3775(2) 0.44980(18) 0.0446(9) Uani 1 1 d . . . . .
H2A H 0.6363 0.3604 0.4621 0.067 Uiso 1 1 calc GR . . . .
H2B H 0.3944 0.3821 0.4860 0.067 Uiso 1 1 calc GR . . . .
H2C H 0.5055 0.4228 0.4300 0.067 Uiso 1 1 calc GR . . . .
C1 C 0.3486(8) 0.25401(19) 0.43492(19) 0.0427(9) Uani 1 1 d . . . . .
H1A H 0.2828 0.2219 0.4053 0.064 Uiso 1 1 calc GR . . . .
H1B H 0.2490 0.2588 0.4702 0.064 Uiso 1 1 calc GR . . . .
H1C H 0.4928 0.2360 0.4486 0.064 Uiso 1 1 calc GR . . . .
C3 C 0.1598(7) 0.3520(2) 0.3770(3) 0.0522(11) Uani 1 1 d . . . . .
H3A H 0.1841 0.3966 0.3566 0.078 Uiso 1 1 calc GR . . . .
H3B H 0.0506 0.3579 0.4100 0.078 Uiso 1 1 calc GR . . . .
H3C H 0.1037 0.3183 0.3473 0.078 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C8 1.228(4) . ?
O1 C5 1.353(4) . ?
O1 C4 1.463(4) . ?
O4 C12 1.231(4) . ?
O6 C14 1.331(4) . ?
O6 C15 1.450(4) . ?
O2 C5 1.220(4) . ?
O5 C14 1.210(4) . ?
N2 H2 0.8600 . ?
N2 C8 1.353(4) . ?
N2 C9 1.458(4) . ?
N1 H1 0.8600 . ?
N1 C5 1.340(4) . ?
N1 C6 1.461(4) . ?
N3 H3 0.8600 . ?
N3 C12 1.336(4) . ?
N3 C13 1.452(4) . ?
C8 C6 1.530(4) . ?
C12 C9 1.541(4) . ?
C17 C16 1.506(4) . ?
C17 C18 1.395(5) . ?
C17 C22 1.399(5) . ?
C13 H13 0.9800 . ?
C13 C16 1.534(4) . ?
C13 C14 1.523(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 H6 0.9800 . ?
C6 C7 1.513(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11 C9 1.526(4) . ?
C9 C10 1.540(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.375(5) . ?
C19 C20 1.396(5) . ?
C4 C2 1.519(5) . ?
C4 C1 1.522(5) . ?
C4 C3 1.516(5) . ?
C18 H18 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C21 1.379(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(6) . ?
C21 H21 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 120.9(2) . . ?
C14 O6 C15 115.5(3) . . ?
C8 N2 H2 118.7 . . ?
C8 N2 C9 122.6(2) . . ?
C9 N2 H2 118.7 . . ?
C5 N1 H1 120.1 . . ?
C5 N1 C6 119.9(2) . . ?
C6 N1 H1 120.1 . . ?
C12 N3 H3 120.2 . . ?
C12 N3 C13 119.6(3) . . ?
C13 N3 H3 120.2 . . ?
O3 C8 N2 123.4(3) . . ?
O3 C8 C6 122.2(3) . . ?
N2 C8 C6 114.4(3) . . ?
O4 C12 N3 121.7(3) . . ?
O4 C12 C9 120.2(3) . . ?
N3 C12 C9 117.8(3) . . ?
O2 C5 O1 125.8(3) . . ?
O2 C5 N1 124.4(3) . . ?
N1 C5 O1 109.8(3) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 C22 118.1(3) . . ?
C22 C17 C16 120.9(3) . . ?
N3 C13 H13 109.5 . . ?
N3 C13 C16 109.4(2) . . ?
N3 C13 C14 110.0(2) . . ?
C16 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C14 C13 C16 108.9(2) . . ?
C17 C16 C13 112.6(2) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C13 C16 H16A 109.1 . . ?
C13 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
O6 C14 C13 111.2(3) . . ?
O5 C14 O6 124.4(3) . . ?
O5 C14 C13 124.3(3) . . ?
N1 C6 C8 109.2(2) . . ?
N1 C6 H6 109.7 . . ?
N1 C6 C7 109.6(2) . . ?
C8 C6 H6 109.7 . . ?
C7 C6 C8 108.9(3) . . ?
C7 C6 H6 109.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
N2 C9 C12 111.0(3) . . ?
N2 C9 C11 111.8(2) . . ?
N2 C9 C10 107.3(2) . . ?
C11 C9 C12 110.5(3) . . ?
C11 C9 C10 110.2(3) . . ?
C10 C9 C12 105.8(2) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
O1 C4 C2 110.1(3) . . ?
O1 C4 C1 102.0(3) . . ?
O1 C4 C3 110.0(3) . . ?
C2 C4 C1 110.7(3) . . ?
C3 C4 C2 113.2(3) . . ?
C3 C4 C1 110.3(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C22 H22 119.7 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.125 0.211 0.401 13.6 0.5 ?
2 -0.100 0.228 0.903 8.6 0.3 ?
3 0.125 0.711 0.099 13.6 0.5 ?
4 0.100 0.728 0.597 8.6 0.3 ?
5 0.375 0.289 0.599 13.6 0.5 ?
6 0.400 0.272 0.097 8.6 0.3 ?
7 0.600 0.772 0.403 8.6 0.3 ?
8 0.625 0.789 0.901 13.6 0.5 ?


_olex2_date_sample_data_collection 2019-12-09
_olex2_submission_special_instructions 'No special instructions were received'
