# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_rb47
_database_code_depnum_ccdc_archive 'CCDC 2275179'
loop_
_audit_author_name
_audit_author_address
'Vemula arunkumar'
;university of Hyderbad
India
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2023-02-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N O3'
_chemical_formula_sum            'C15 H14 N O3'
_chemical_formula_weight         256.27
_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 0.0033 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      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                   8.6191(4)
_cell_length_b                   8.8839(4)
_cell_length_c                   9.3999(3)
_cell_angle_alpha                81.898(3)
_cell_angle_beta                 73.226(3)
_cell_angle_gamma                73.495(4)
_cell_volume                     659.38(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5392
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.2030
_cell_measurement_theta_min      2.2630
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15968
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  86.00   0.50    2.00    --   16.22  61.00 -30.00  194
  2  ω     -7.00  58.00   0.50    2.00    --   16.22-104.00-115.00  130
  3  ω     10.00  71.00   0.50    2.00    --   16.22-125.00-180.00  122
  4  ω    -37.00  21.00   0.50    2.00    --  -15.60 -94.00-180.00  116
  5  ω    -41.00  58.00   0.50    2.00    --  -15.60  30.00 -90.00  198
  6  ω     -8.00  86.00   0.50    2.00    --   16.22  45.00-180.00  188
  7  ω    -43.00  54.00   0.50    2.00    --  -15.60  61.00-180.00  194
  8  ω    -37.00  21.00   0.50    2.00    --  -15.60 -94.00 -60.00  116
  9  ω    -54.00  41.00   0.50    2.00    --   16.22 -45.00 -30.00  190
 10  ω    -53.00  44.00   0.50    2.00    --   16.22 -61.00  30.00  194
 11  ω    -37.00  21.00   0.50    2.00    --  -15.60 -94.00 120.00  116
 12  ω    -57.00  41.00   0.50    2.00    --   16.22 -30.00  60.00  196
 13  ω    -10.00  90.00   0.50    2.00    --   16.22  30.00 120.00  200
 14  ω    -42.00 -14.00   0.50    2.00    --   16.22 133.00  39.16   56
 15  ω    -57.00   7.00   0.50    2.00    --  -15.60 104.00 -14.00  128
 16  ω    -57.00  41.00   0.50    2.00    --   16.22 -30.00 -90.00  196
 17  ω    -70.00 -10.00   0.50    2.00    --  -15.60 125.00-120.00  120
 18  ω    -89.00   9.00   0.50    2.00    --  -15.60 -30.00-150.00  196
 19  ω    -88.00  16.00   0.50    2.00    --  -15.60 -77.00-150.00  208
 20  ω    -88.00  16.00   0.50    2.00    --  -15.60 -77.00   0.00  208
 21  ω    -85.00  -4.00   0.50    2.00    --  -15.60 -61.00  30.00  162
 22  ω    -70.00 -10.00   0.50    2.00    --  -15.60 125.00   0.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0039147000
_diffrn_orient_matrix_UB_12      0.0774981000
_diffrn_orient_matrix_UB_13      -0.0327811000
_diffrn_orient_matrix_UB_21      -0.0536696000
_diffrn_orient_matrix_UB_22      0.0309248000
_diffrn_orient_matrix_UB_23      0.0678486000
_diffrn_orient_matrix_UB_31      0.0708052000
_diffrn_orient_matrix_UB_32      0.0008103000
_diffrn_orient_matrix_UB_33      0.0236414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1563
_reflns_number_total             2817
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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         0.399
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.047
_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)+(0.1084P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2301
_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. Others
 Fixed Sof: H13(0.5) H13A(0.5) C14B(0.5) H14A(0.5) H14B(0.5) H14C(0.5)
 C14A(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C10(H10), C9(H9), C13(H13), C13(H13A)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14B(H14A,H14B,H14C), C14A(H14D,H14E,H14F)
;
_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
N1 N 0.3536(2) 0.4022(2) 0.1507(2) 0.0629(6) Uani 1 1 d . . . . .
O2 O 0.1161(3) 0.6157(3) 0.4993(2) 0.0980(7) Uani 1 1 d . . . . .
O1 O 0.1875(3) 0.3067(3) 0.0545(3) 0.1015(8) Uani 1 1 d . . . . .
C4 C 0.3478(3) 0.5340(3) 0.2196(3) 0.0594(6) Uani 1 1 d . . . . .
C6 C 0.5983(3) 0.3635(3) 0.2047(3) 0.0597(6) Uani 1 1 d . . . . .
O3 O -0.0576(3) 0.7902(3) 0.3917(3) 0.1275(10) Uani 1 1 d . . . . .
C7 C 0.5077(3) 0.2952(3) 0.1411(3) 0.0612(6) Uani 1 1 d . . . . .
C5 C 0.4940(3) 0.5170(3) 0.2524(3) 0.0614(6) Uani 1 1 d . . . . .
C0AA C 0.2082(3) 0.4089(4) 0.1141(3) 0.0735(8) Uani 1 1 d . . . . .
C3 C 0.1784(3) 0.6459(3) 0.2328(3) 0.0686(7) Uani 1 1 d . . . . .
H3 H 0.190054 0.744188 0.173843 0.082 Uiso 1 1 calc R . . . .
C12 C 0.0818(4) 0.6812(3) 0.3901(3) 0.0740(8) Uani 1 1 d . . . . .
C11 C 0.7578(3) 0.2776(3) 0.2120(3) 0.0742(8) Uani 1 1 d . . . . .
H11 H 0.820949 0.318820 0.253994 0.089 Uiso 1 1 calc R . . . .
C8 C 0.5702(4) 0.1486(3) 0.0872(3) 0.0797(8) Uani 1 1 d . . . . .
H8 H 0.507200 0.105687 0.046473 0.096 Uiso 1 1 calc R . . . .
C2 C 0.0868(4) 0.5606(4) 0.1635(3) 0.0823(9) Uani 1 1 d . . . . .
H2A H -0.012290 0.541464 0.236571 0.099 Uiso 1 1 calc R . . . .
H2B H 0.052811 0.623930 0.079465 0.099 Uiso 1 1 calc R . . . .
C10 C 0.8217(4) 0.1313(4) 0.1567(4) 0.0876(9) Uani 1 1 d . . . . .
H10 H 0.929286 0.074232 0.160588 0.105 Uiso 1 1 calc R . . . .
C15 C 0.5436(4) 0.6298(3) 0.3223(4) 0.0855(9) Uani 1 1 d . . . . .
H15A H 0.608139 0.688352 0.246196 0.128 Uiso 1 1 calc GR . . . .
H15B H 0.609726 0.573054 0.388614 0.128 Uiso 1 1 calc GR . . . .
H15C H 0.444844 0.700849 0.377109 0.128 Uiso 1 1 calc GR . . . .
C9 C 0.7291(4) 0.0671(4) 0.0952(4) 0.0888(9) Uani 1 1 d . . . . .
H9 H 0.775023 -0.032522 0.058766 0.107 Uiso 1 1 calc R . . . .
C13 C -0.1885(8) 0.8203(7) 0.5338(5) 0.158(2) Uani 1 1 d . . . . .
H13 H -0.261098 0.758848 0.584475 0.190 Uiso 0.5 1 calc R . P A 1
H13A H -0.179012 0.762886 0.622962 0.190 Uiso 0.5 1 calc R . P B 2
C14B C -0.3158(11) 0.9326(13) 0.5220(10) 0.133(3) Uani 0.5 1 d . . P C 2
H14A H -0.399992 0.940369 0.615225 0.200 Uiso 0.5 1 calc GR . P C 2
H14B H -0.360209 0.912443 0.445997 0.200 Uiso 0.5 1 calc GR . P C 2
H14C H -0.282834 1.029552 0.495771 0.200 Uiso 0.5 1 calc GR . P C 2
C14A C -0.180(2) 0.9443(18) 0.5695(14) 0.186(5) Uani 0.5 1 d . . P C 1
H14D H -0.154164 1.012322 0.481943 0.278 Uiso 0.5 1 calc GR . P C 1
H14E H -0.092901 0.923577 0.620100 0.278 Uiso 0.5 1 calc GR . P C 1
H14F H -0.284981 0.994284 0.634479 0.278 Uiso 0.5 1 calc GR . P C 1


_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
N1 C4 1.398(3) . ?
N1 C7 1.383(3) . ?
N1 C0AA 1.376(3) . ?
O2 C12 1.179(3) . ?
O1 C0AA 1.209(3) . ?
C4 C5 1.345(3) . ?
C4 C3 1.497(3) . ?
C6 C7 1.405(3) . ?
C6 C5 1.454(3) . ?
C6 C11 1.386(4) . ?
O3 C12 1.309(3) . ?
O3 C13 1.479(5) . ?
C7 C8 1.369(4) . ?
C5 C15 1.486(3) . ?
C0AA C2 1.491(4) . ?
C3 H3 0.9800 . ?
C3 C12 1.500(4) . ?
C3 C2 1.549(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.371(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C9 1.384(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C13 H13A 0.9300 . ?
C13 C14B 1.276(9) . ?
C13 C14A 1.225(11) . ?
C14B H14A 0.9600 . ?
C14B H14B 0.9600 . ?
C14B H14C 0.9600 . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 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
C7 N1 C4 109.13(19) . . ?
C0AA N1 C4 114.2(2) . . ?
C0AA N1 C7 136.6(2) . . ?
N1 C4 C3 108.2(2) . . ?
C5 C4 N1 110.2(2) . . ?
C5 C4 C3 141.6(2) . . ?
C7 C6 C5 108.3(2) . . ?
C11 C6 C7 118.0(2) . . ?
C11 C6 C5 133.7(2) . . ?
C12 O3 C13 119.3(3) . . ?
N1 C7 C6 106.3(2) . . ?
C8 C7 N1 130.8(2) . . ?
C8 C7 C6 122.8(3) . . ?
C4 C5 C6 106.0(2) . . ?
C4 C5 C15 128.2(3) . . ?
C6 C5 C15 125.8(2) . . ?
N1 C0AA C2 107.3(2) . . ?
O1 C0AA N1 124.5(3) . . ?
O1 C0AA C2 128.3(3) . . ?
C4 C3 H3 109.7 . . ?
C4 C3 C12 113.8(2) . . ?
C4 C3 C2 103.8(2) . . ?
C12 C3 H3 109.7 . . ?
C12 C3 C2 110.2(2) . . ?
C2 C3 H3 109.7 . . ?
O2 C12 O3 123.0(3) . . ?
O2 C12 C3 126.7(3) . . ?
O3 C12 C3 110.1(2) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 C6 119.5(3) . . ?
C10 C11 H11 120.3 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.7(3) . . ?
C9 C8 H8 121.1 . . ?
C0AA C2 C3 106.5(2) . . ?
C0AA C2 H2A 110.4 . . ?
C0AA C2 H2B 110.4 . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C11 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O3 C13 H13 127.8 . . ?
O3 C13 H13A 123.3 . . ?
C14B C13 O3 113.4(5) . . ?
C14B C13 H13A 123.3 . . ?
C14A C13 O3 104.4(9) . . ?
C14A C13 H13 127.8 . . ?
C13 C14B H14A 109.5 . . ?
C13 C14B H14B 109.5 . . ?
C13 C14B H14C 109.5 . . ?
H14A C14B H14B 109.5 . . ?
H14A C14B H14C 109.5 . . ?
H14B C14B H14C 109.5 . . ?
C13 C14A H14D 109.5 . . ?
C13 C14A H14E 109.5 . . ?
C13 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.869
_oxdiff_exptl_absorpt_empirical_full_min 0.468
####################################################################### 
# 
# 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_rb54
_database_code_depnum_ccdc_archive 'CCDC 2277539'
loop_
_audit_author_name
_audit_author_address
'Vemula arunkumar'
;university of Hyderbad
India
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 N2 O4'
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51
_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 0.0033 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      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                   7.8862(5)
_cell_length_b                   12.8660(12)
_cell_length_c                   12.9041(13)
_cell_angle_alpha                109.715(9)
_cell_angle_beta                 97.202(7)
_cell_angle_gamma                106.377(7)
_cell_volume                     1146.77(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4361
_cell_measurement_temperature    295.83
_cell_measurement_theta_max      21.6250
_cell_measurement_theta_min      2.7150
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3342
_diffrn_reflns_av_unetI/netI     0.2730
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23284
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.712
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_min         1.943
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.83
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  54.00   0.50    4.00    --  -15.60  61.00   0.00  194
  2  ω    -15.00  89.00   0.50    4.00    --   16.22  77.00 -60.00  208
  3  ω    -15.00  89.00   0.50    4.00    --   16.22  77.00-150.00  208
  4  ω    -10.00  90.00   0.50    4.00    --   16.22  30.00-180.00  200
  5  ω    -41.00  58.00   0.50    4.00    --  -15.60  30.00 -60.00  198
  6  ω    -37.00  21.00   0.50    4.00    --  -15.60 -94.00-120.00  116
  7  ω     28.00  91.00   0.50    4.00    --   16.22-158.00 -95.00  126
  8  ω    -37.00  21.00   0.50    4.00    --  -15.60 -94.00   0.00  116
  9  ω      5.00  66.00   0.50    4.00    --   16.22-118.00  58.00  122
 10  ω    -37.00  21.00   0.50    4.00    --  -15.60 -94.00 120.00  116
 11  ω    -37.00  53.00   0.50    4.00    --   16.22 -94.00  90.00  180
 12  ω    -37.00  15.00   0.50    4.00    --  -15.60 -94.00  30.00  104
 13  ω    -54.00  41.00   0.50    4.00    --   16.22 -45.00  90.00  190
 14  ω    -10.00  90.00   0.50    4.00    --   16.22  30.00  60.00  200
 15  ω    -66.00  -5.00   0.50    4.00    --  -15.60 118.00 144.00  122
 16  ω    -70.00 -10.00   0.50    4.00    --  -15.60 125.00 -90.00  120
 17  ω    -70.00 -10.00   0.50    4.00    --  -15.60 125.00-150.00  120
 18  ω    -40.00  55.00   0.50    4.00    --  -15.60  45.00-180.00  190
 19  ω    -90.00 -28.00   0.50    4.00    --  -15.60 158.00 -61.00  124
 20  ω    -89.00   9.00   0.50    4.00    --  -15.60 -30.00-150.00  196
 21  ω    -85.00  12.00   0.50    4.00    --  -15.60 -61.00  60.00  194
 22  ω    -89.00   9.00   0.50    4.00    --  -15.60 -30.00 120.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221715000
_diffrn_orient_matrix_UB_12      -0.0087570000
_diffrn_orient_matrix_UB_13      -0.0580279000
_diffrn_orient_matrix_UB_21      0.0435740000
_diffrn_orient_matrix_UB_22      0.0611495000
_diffrn_orient_matrix_UB_23      0.0148466000
_diffrn_orient_matrix_UB_31      0.0833955000
_diffrn_orient_matrix_UB_32      -0.0091472000
_diffrn_orient_matrix_UB_33      -0.0061458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1155
_reflns_number_total             3915
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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         0.276
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3194
_refine_ls_R_factor_gt           0.1744
_refine_ls_restrained_S_all      1.198
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3970
_refine_ls_wR_factor_ref         0.5818
_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:
 C25(H25A,H25B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C2(H2), C5(H5), C19(H19), C16(H16), C3(H3), C18(H18),
 C4(H4), C17(H17)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.9664(11) 0.6506(11) 0.4057(8) 0.110(4) Uani 1 1 d . . . . .
O4 O 0.3254(9) 0.6132(8) -0.0373(6) 0.102(3) Uani 1 1 d . . . . .
O1 O 1.0423(10) 0.8424(9) 0.4645(8) 0.110(3) Uani 1 1 d . . . . .
N1 N 1.0998(10) 0.8130(9) 0.2088(9) 0.088(3) Uani 1 1 d . . . . .
C12 C 0.6190(12) 0.7002(11) 0.0817(10) 0.083(4) Uani 1 1 d . . . . .
N2 N 0.3495(12) 0.5293(11) 0.4004(11) 0.098(3) Uani 1 1 d . . . . .
C8 C 0.9160(12) 0.7643(11) 0.2057(10) 0.085(4) Uani 1 1 d . . . . .
C21 C 0.9505(16) 0.7322(17) 0.3909(13) 0.096(5) Uani 1 1 d . . . . .
C14 C 0.4224(13) 0.5348(12) 0.3130(11) 0.090(4) Uani 1 1 d . . . . .
H14 H 0.387217 0.473562 0.241907 0.108 Uiso 1 1 calc R . . . .
C6 C 0.9339(13) 0.8026(11) 0.0437(11) 0.092(4) Uani 1 1 d . . . . .
C13 C 0.5564(13) 0.6430(12) 0.3421(10) 0.083(4) Uani 1 1 d . . . . .
C11 C 0.5467(12) 0.6642(11) 0.1609(10) 0.089(4) Uani 1 1 d . . . . .
H11 H 0.421211 0.627644 0.145271 0.107 Uiso 1 1 calc R . . . .
C9 C 0.8406(12) 0.7292(10) 0.2861(10) 0.086(4) Uani 1 1 d . . . . .
C7 C 0.8091(13) 0.7557(11) 0.1037(10) 0.080(4) Uani 1 1 d . . . . .
C24 C 0.4932(15) 0.6775(13) -0.0260(12) 0.097(5) Uani 1 1 d . . . . .
C25 C 0.1972(13) 0.5848(12) -0.1427(11) 0.104(5) Uani 1 1 d . . . . .
H25A H 0.230052 0.536575 -0.207212 0.125 Uiso 1 1 calc R . . . .
H25B H 0.195374 0.656008 -0.152510 0.125 Uiso 1 1 calc R . . . .
C2 C 1.2651(15) 0.8834(13) 0.0818(13) 0.112(5) Uani 1 1 d . . . . .
H2 H 1.380781 0.902165 0.125599 0.134 Uiso 1 1 calc R . . . .
C10 C 0.6527(12) 0.6800(11) 0.2627(9) 0.083(4) Uani 1 1 d . . . . .
C1 C 1.1088(14) 0.8345(12) 0.1127(11) 0.093(4) Uani 1 1 d . . . . .
C5 C 0.9179(17) 0.8237(13) -0.0551(11) 0.111(5) Uani 1 1 d . . . . .
H5 H 0.802438 0.803400 -0.100115 0.134 Uiso 1 1 calc R . . . .
C20 C 0.5652(14) 0.7055(13) 0.4620(11) 0.087(4) Uani 1 1 d . . . . .
C15 C 0.4350(15) 0.6345(15) 0.4947(13) 0.104(5) Uani 1 1 d . . . . .
C19 C 0.6702(15) 0.8200(14) 0.5405(11) 0.100(4) Uani 1 1 d . . . . .
H19 H 0.751361 0.872555 0.519418 0.120 Uiso 1 1 calc R . . . .
C28 C 1.2573(12) 0.8237(12) 0.2883(11) 0.103(5) Uani 1 1 d . . . . .
H28A H 1.280879 0.889897 0.357968 0.154 Uiso 1 1 calc GR . . . .
H28B H 1.361439 0.834881 0.256443 0.154 Uiso 1 1 calc GR . . . .
H28C H 1.233813 0.753221 0.302953 0.154 Uiso 1 1 calc GR . . . .
O3 O 0.5345(13) 0.7130(16) -0.0945(11) 0.208(8) Uani 1 1 d . . . . .
C16 C 0.411(2) 0.6666(18) 0.6004(16) 0.116(5) Uani 1 1 d . . . . .
H16 H 0.322229 0.616829 0.620061 0.139 Uiso 1 1 calc R . . . .
C3 C 1.241(2) 0.9023(15) -0.0144(15) 0.132(6) Uani 1 1 d . . . . .
H3 H 1.345611 0.936833 -0.034233 0.158 Uiso 1 1 calc R . . . .
C18 C 0.6483(19) 0.8516(14) 0.6502(12) 0.115(5) Uani 1 1 d . . . . .
H18 H 0.720331 0.925299 0.705024 0.138 Uiso 1 1 calc R . . . .
C22 C 1.1578(17) 0.8545(15) 0.5675(13) 0.131(6) Uani 1 1 d . . . . .
H22A H 1.261702 0.831843 0.550494 0.158 Uiso 1 1 calc R . . . .
H22B H 1.090146 0.803405 0.600231 0.158 Uiso 1 1 calc R . . . .
C4 C 1.0713(17) 0.8746(13) -0.0885(12) 0.117(5) Uani 1 1 d . . . . .
H4 H 1.062713 0.889224 -0.154488 0.140 Uiso 1 1 calc R . . . .
C27 C 0.1989(14) 0.4305(13) 0.3998(12) 0.119(5) Uani 1 1 d . . . . .
H27A H 0.097297 0.455463 0.414278 0.179 Uiso 1 1 calc GR . . . .
H27B H 0.238319 0.405404 0.457751 0.179 Uiso 1 1 calc GR . . . .
H27C H 0.162875 0.366356 0.327090 0.179 Uiso 1 1 calc GR . . . .
C17 C 0.522(2) 0.776(2) 0.6790(14) 0.120(6) Uani 1 1 d . . . . .
H17 H 0.511121 0.799073 0.753580 0.144 Uiso 1 1 calc R . . . .
C26 C 0.0120(14) 0.5174(13) -0.1315(12) 0.125(6) Uani 1 1 d . . . . .
H26A H -0.079785 0.497466 -0.198192 0.188 Uiso 1 1 calc GR . . . .
H26B H -0.016456 0.565586 -0.066019 0.188 Uiso 1 1 calc GR . . . .
H26C H 0.015909 0.446621 -0.123153 0.188 Uiso 1 1 calc GR . . . .
C23 C 1.2206(19) 0.9779(16) 0.6485(14) 0.156(7) Uani 1 1 d . . . . .
H23A H 1.314595 1.025007 0.625959 0.235 Uiso 1 1 calc GR . . . .
H23B H 1.267854 0.983023 0.723053 0.235 Uiso 1 1 calc GR . . . .
H23C H 1.120202 1.006251 0.649455 0.235 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C21 1.165(16) . ?
O4 C24 1.307(13) . ?
O4 C25 1.455(13) . ?
O1 C21 1.333(17) . ?
O1 C22 1.449(15) . ?
N1 C8 1.398(11) . ?
N1 C1 1.365(14) . ?
N1 C28 1.450(14) . ?
C12 C11 1.379(15) . ?
C12 C7 1.411(13) . ?
C12 C24 1.489(17) . ?
N2 C14 1.341(14) . ?
N2 C15 1.391(15) . ?
N2 C27 1.472(14) . ?
C8 C9 1.396(16) . ?
C8 C7 1.424(15) . ?
C21 C9 1.495(18) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(15) . ?
C6 C7 1.450(15) . ?
C6 C1 1.410(15) . ?
C6 C5 1.388(17) . ?
C13 C10 1.474(15) . ?
C13 C20 1.465(16) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(15) . ?
C9 C10 1.385(12) . ?
C24 O3 1.165(14) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.526(15) . ?
C2 H2 0.9300 . ?
C2 C1 1.388(15) . ?
C2 C3 1.34(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.398(15) . ?
C20 C15 1.382(17) . ?
C20 C19 1.406(17) . ?
C15 C16 1.340(18) . ?
C19 H19 0.9300 . ?
C19 C18 1.382(17) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.38(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.420(18) . ?
C18 H18 0.9300 . ?
C18 C17 1.37(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.472(19) . ?
C4 H4 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C17 H17 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C24 O4 C25 115.6(10) . . ?
C21 O1 C22 115.5(12) . . ?
C8 N1 C28 127.7(11) . . ?
C1 N1 C8 107.9(9) . . ?
C1 N1 C28 123.8(9) . . ?
C11 C12 C7 119.5(10) . . ?
C11 C12 C24 118.7(9) . . ?
C7 C12 C24 121.8(11) . . ?
C14 N2 C15 109.7(11) . . ?
C14 N2 C27 126.9(12) . . ?
C15 N2 C27 123.4(11) . . ?
N1 C8 C7 108.3(10) . . ?
C9 C8 N1 128.4(11) . . ?
C9 C8 C7 123.2(9) . . ?
O2 C21 O1 122.8(14) . . ?
O2 C21 C9 125.7(16) . . ?
O1 C21 C9 111.4(15) . . ?
N2 C14 H14 124.3 . . ?
N2 C14 C13 111.5(12) . . ?
C13 C14 H14 124.3 . . ?
C1 C6 C7 104.7(12) . . ?
C5 C6 C7 136.0(10) . . ?
C5 C6 C1 119.3(11) . . ?
C14 C13 C10 124.7(11) . . ?
C14 C13 C20 103.4(11) . . ?
C20 C13 C10 131.8(12) . . ?
C12 C11 H11 118.6 . . ?
C12 C11 C10 122.9(9) . . ?
C10 C11 H11 118.6 . . ?
C8 C9 C21 124.0(9) . . ?
C10 C9 C8 117.9(11) . . ?
C10 C9 C21 117.9(12) . . ?
C12 C7 C8 116.4(10) . . ?
C12 C7 C6 136.1(11) . . ?
C8 C7 C6 107.4(9) . . ?
O4 C24 C12 113.1(12) . . ?
O3 C24 O4 121.7(12) . . ?
O3 C24 C12 125.2(12) . . ?
O4 C25 H25A 110.7 . . ?
O4 C25 H25B 110.7 . . ?
O4 C25 C26 105.3(11) . . ?
H25A C25 H25B 108.8 . . ?
C26 C25 H25A 110.7 . . ?
C26 C25 H25B 110.7 . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C3 C2 C1 116.8(14) . . ?
C11 C10 C13 117.1(8) . . ?
C11 C10 C9 119.8(11) . . ?
C9 C10 C13 123.1(11) . . ?
N1 C1 C6 111.7(10) . . ?
N1 C1 C2 127.1(13) . . ?
C2 C1 C6 121.2(14) . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.5(13) . . ?
C4 C5 H5 119.3 . . ?
C15 C20 C13 108.9(13) . . ?
C15 C20 C19 118.9(12) . . ?
C19 C20 C13 132.1(12) . . ?
C20 C15 N2 106.5(12) . . ?
C16 C15 N2 130.4(16) . . ?
C16 C15 C20 123.1(16) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 C20 117.6(14) . . ?
C18 C19 H19 121.2 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.6(15) . . ?
C17 C16 H16 121.2 . . ?
C2 C3 H3 116.9 . . ?
C2 C3 C4 126.1(14) . . ?
C4 C3 H3 116.9 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.8(15) . . ?
C17 C18 H18 119.6 . . ?
O1 C22 H22A 109.9 . . ?
O1 C22 H22B 109.9 . . ?
O1 C22 C23 108.8(14) . . ?
H22A C22 H22B 108.3 . . ?
C23 C22 H22A 109.9 . . ?
C23 C22 H22B 109.9 . . ?
C5 C4 C3 115.1(14) . . ?
C5 C4 H4 122.5 . . ?
C3 C4 H4 122.5 . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.7(14) . . ?
C18 C17 H17 119.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.364
_oxdiff_exptl_absorpt_empirical_full_min 0.192
####################################################################### 
# 
# 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_RB001A_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2275329'
loop_
_audit_author_name
_audit_author_address
'Vemula arunkumar'
;university of Hyderbad
India
;
_audit_update_record             
;
2023-06-26 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_audit_creation_date             2021-07-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_chemical_formula_moiety         'C19 H21 N O5'
_chemical_formula_sum            'C19 H21 N O5'
_chemical_formula_weight         343.38
_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4646(7)
_cell_length_b                   21.096(2)
_cell_length_c                   10.1483(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.960(4)
_cell_angle_gamma                90
_cell_volume                     1742.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0999 before and 0.0712 after correction. The Ratio of minimum to maximum transmission is 0.9084. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3089
_exptl_crystal_description       plate
_exptl_crystal_F_000             728.4229
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49348
_diffrn_reflns_theta_full        27.5551
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.93
_diffrn_ambient_temperature      288.0
_diffrn_measured_fraction_theta_full 0.9960
_diffrn_measured_fraction_theta_max 0.9960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2823
_reflns_number_total             4013
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6833
_refine_diff_density_min         -0.4759
_refine_diff_density_rms         0.1334
_refine_ls_d_res_high            0.7682
_refine_ls_d_res_low             10.5481
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.0575
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1195P)²+0.2869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1976
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C15(H15a,H15b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2), C1(H1)
2.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C16(H16a,H16b,H16c), C19(H19a,H19b,H19c)
;
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_refinement_flags_posn
O5 O 0.28200(16) 0.47142(7) 0.36318(14) 0.0557(4) Uani 1.000000 .
O2 O 0.91283(17) 0.29919(7) 0.36124(15) 0.0591(4) Uani 1.000000 .
O4 O 0.25437(18) 0.37717(8) 0.25855(16) 0.0618(4) Uani 1.000000 .
N1 N 0.72032(18) 0.40745(7) 0.10469(15) 0.0441(4) Uani 1.000000 .
C8 C 0.60459(19) 0.42631(8) 0.27504(16) 0.0348(4) Uani 1.000000 .
C5 C 0.6318(2) 0.48593(8) 0.21793(17) 0.0362(4) Uani 1.000000 .
C9 C 0.6582(2) 0.38039(8) 0.20336(17) 0.0382(4) Uani 1.000000 .
C6 C 0.7039(2) 0.47224(9) 0.11223(17) 0.0412(4) Uani 1.000000 .
O1 O 0.4992(2) 0.24539(8) 0.3403(2) 0.0927(7) Uani 1.000000 .
C14 C 0.3392(2) 0.41714(9) 0.32827(18) 0.0440(4) Uani 1.000000 .
C13 C 0.5242(2) 0.41236(9) 0.38585(17) 0.0415(4) Uani 1.000000 .
O3 O 0.8275(3) 0.22696(11) 0.2028(3) 0.1384(12) Uani 1.000000 .
C17 C 0.8051(3) 0.27402(9) 0.2573(2) 0.0592(6) Uani 1.000000 .
C4 C 0.5998(2) 0.54892(9) 0.2440(2) 0.0483(5) Uani 1.000000 .
C10 C 0.6432(2) 0.31060(8) 0.2210(2) 0.0494(5) Uani 1.000000 .
C12 C 0.5711(2) 0.34602(10) 0.4427(2) 0.0544(5) Uani 1.000000 .
C1 C 0.7454(3) 0.51997(11) 0.0327(2) 0.0572(6) Uani 1.000000 .
C2 C 0.7126(3) 0.58128(11) 0.0605(2) 0.0656(7) Uani 1.000000 .
C11 C 0.5607(2) 0.29652(9) 0.3357(2) 0.0573(6) Uani 1.000000 .
C15 C 0.1051(2) 0.48171(12) 0.3145(2) 0.0610(6) Uani 1.000000 .
C3 C 0.6409(3) 0.59594(10) 0.1642(2) 0.0616(6) Uani 1.000000 .
C7 C 0.7919(3) 0.37477(13) 0.0095(3) 0.0700(7) Uani 1.000000 .
C18 C 1.0704(3) 0.26696(13) 0.4105(3) 0.0736(7) Uani 1.000000 .
C16 C 0.0728(3) 0.54588(14) 0.3606(3) 0.0785(8) Uani 1.000000 .
C19 C 1.1568(3) 0.2969(2) 0.5441(3) 0.1061(12) Uani 1.000000 .
H4 H 0.5518(2) 0.55907(9) 0.3134(2) 0.0579(6) Uiso 1.000000 R
H3 H 0.6202(3) 0.63810(10) 0.1804(2) 0.0739(7) Uiso 1.000000 R
H2 H 0.7390(3) 0.61388(11) 0.0086(2) 0.0787(8) Uiso 1.000000 R
H1 H 0.7938(3) 0.51046(11) -0.0369(2) 0.0686(7) Uiso 1.000000 R
H13 H 0.5611(2) 0.44341(9) 0.45977(17) 0.0498(5) Uiso 1.000000 R
H10 H 0.5731(2) 0.29333(8) 0.1350(2) 0.0593(6) Uiso 1.000000 R
H12a H 0.6825(2) 0.34711(10) 0.5020(2) 0.0653(6) Uiso 1.000000 R
H12b H 0.4993(2) 0.33402(10) 0.4984(2) 0.0653(6) Uiso 1.000000 R
H15a H 0.0686(2) 0.47899(12) 0.2153(2) 0.0733(7) Uiso 1.000000 R
H15b H 0.0471(2) 0.44998(12) 0.3524(2) 0.0733(7) Uiso 1.000000 R
H7a H 0.9092(4) 0.3736(8) 0.0460(9) 0.1049(10) Uiso 1.000000 GR
H7b H 0.7501(18) 0.3323(3) -0.0038(15) 0.1049(10) Uiso 1.000000 GR
H7c H 0.764(2) 0.3967(5) -0.0766(7) 0.1049(10) Uiso 1.000000 GR
H18a H 1.0538(3) 0.22209(13) 0.4229(3) 0.0884(9) Uiso 1.000000 R
H18b H 1.1346(3) 0.27179(13) 0.3454(3) 0.0884(9) Uiso 1.000000 R
H16a H 0.129(2) 0.57687(16) 0.3206(18) 0.1177(12) Uiso 1.000000 GR
H16b H -0.0432(4) 0.5541(4) 0.332(2) 0.1177(12) Uiso 1.000000 GR
H16c H 0.112(2) 0.5482(3) 0.4587(3) 0.1177(12) Uiso 1.000000 GR
H19a H 1.176(3) 0.3410(4) 0.5298(5) 0.1592(18) Uiso 1.000000 GR
H19b H 1.0902(16) 0.2931(12) 0.6065(9) 0.1592(18) Uiso 1.000000 GR
H19c H 1.2601(16) 0.2761(9) 0.5818(14) 0.1592(18) Uiso 1.000000 GR


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
O5 C14 1.329(2) . ?
O5 C15 1.458(2) . ?
O2 C17 1.303(2) . ?
O2 C18 1.458(3) . ?
O4 C14 1.203(2) . ?
N1 C9 1.376(2) . ?
N1 C6 1.378(2) . ?
N1 C7 1.448(3) . ?
C8 C5 1.430(2) . ?
C8 C9 1.362(2) . ?
C8 C13 1.495(2) . ?
C5 C6 1.402(3) . ?
C5 C4 1.396(2) . ?
C9 C10 1.493(2) . ?
C6 C1 1.395(3) . ?
O1 C11 1.204(2) . ?
C14 C13 1.517(2) . ?
C13 C12 1.524(3) . ?
O3 C17 1.177(3) . ?
C17 C10 1.527(3) . ?
C4 C3 1.385(3) . ?
C10 C11 1.542(3) . ?
C12 C11 1.492(3) . ?
C1 C2 1.369(3) . ?
C2 C3 1.386(3) . ?
C15 C16 1.482(3) . ?
C18 C19 1.492(4) . ?

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
C15 O5 C14 116.97(15) . . ?
C18 O2 C17 117.30(18) . . ?
C6 N1 C9 107.84(14) . . ?
C7 N1 C9 126.95(17) . . ?
C7 N1 C6 125.20(17) . . ?
C9 C8 C5 107.14(15) . . ?
C13 C8 C5 129.45(15) . . ?
C13 C8 C9 123.32(15) . . ?
C6 C5 C8 106.35(14) . . ?
C4 C5 C8 134.35(17) . . ?
C4 C5 C6 119.28(16) . . ?
C8 C9 N1 110.09(15) . . ?
C10 C9 N1 123.94(16) . . ?
C10 C9 C8 125.86(17) . . ?
C5 C6 N1 108.57(15) . . ?
C1 C6 N1 129.68(18) . . ?
C1 C6 C5 121.75(18) . . ?
O4 C14 O5 123.94(17) . . ?
C13 C14 O5 111.58(15) . . ?
C13 C14 O4 124.48(18) . . ?
C14 C13 C8 109.42(14) . . ?
C12 C13 C8 109.90(15) . . ?
C12 C13 C14 109.91(15) . . ?
O3 C17 O2 123.8(2) . . ?
C10 C17 O2 111.81(17) . . ?
C10 C17 O3 124.2(2) . . ?
C3 C4 C5 118.5(2) . . ?
C17 C10 C9 115.28(16) . . ?
C11 C10 C9 110.57(16) . . ?
C11 C10 C17 106.45(17) . . ?
C11 C12 C13 114.20(16) . . ?
C2 C1 C6 117.7(2) . . ?
C3 C2 C1 121.57(19) . . ?
C10 C11 O1 119.5(2) . . ?
C12 C11 O1 122.6(2) . . ?
C12 C11 C10 117.81(16) . . ?
C16 C15 O5 106.89(17) . . ?
C2 C3 C4 121.2(2) . . ?
C19 C18 O2 106.7(2) . . ?

loop_
_atom_type.symbol
_atom_type.scat_dispersion_real
_atom_type.scat_dispersion_imag
_atom_type.scat_Cromer_Mann_a1
_atom_type.scat_Cromer_Mann_a2
_atom_type.scat_Cromer_Mann_a3
_atom_type.scat_Cromer_Mann_a4
_atom_type.scat_Cromer_Mann_b1
_atom_type.scat_Cromer_Mann_b2
_atom_type.scat_Cromer_Mann_b3
_atom_type.scat_Cromer_Mann_b4
_atom_type.scat_Cromer_Mann_c
_atom_type.scat_source
_atom_type.scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_olex2_submission_special_instructions 'No special instructions were received'
