# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_raf-ram-040_mo
_database_code_depnum_ccdc_archive 'CCDC 2190081'
loop_
_audit_author_name
_audit_author_address
'Darshan Mhatre'
;Indian Institute of Technology Bombay Mumbai
India
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19.52 N2 O9'
_chemical_formula_sum            'C22 H19.52 N2 O9'
_chemical_formula_weight         455.92
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.892(2)
_cell_length_b                   4.6144(5)
_cell_length_c                   16.629(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.720(18)
_cell_angle_gamma                90
_cell_volume                     1038.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7460
_cell_measurement_theta_min      2.4590
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             475
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.1167
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9785
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.405
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00   16.00    --  -20.00   0.00 108.00  180
  2  ω    -66.00   7.00   1.00   16.00    --  -20.00 -72.00  36.00   73
  3  ω   -110.00  53.00   1.00   16.00    --  -20.00   0.00  36.00  163
  4  ω    -69.00  12.00   1.00   16.00    --  -20.00 -72.00 -36.00   81
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2199
_reflns_number_total             3601
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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         0.232
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.008
_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)+(0.0355P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C00X-C00W
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C00X) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C00Y) \\sim Ueq, Uanis(C00W)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
4. Others
 Sof(H00V)=Sof(C1)=Sof(H1)=1-FVAR(1)
 Sof(C00W)=Sof(H00W)=FVAR(1)
 Sof(C00Y)=Sof(H00N)=Sof(H00T)=1-FVAR(2)
 Sof(C00X)=Sof(H00I)=Sof(H00J)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C00K(H00K), C00S(H00S), C00V(H00V)
5.b Secondary CH2 refined with riding coordinates:
 C00H(H00B,H00C), C00J(H00D,H00E), C00T(H00G,H00H)
5.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00W(H00W), C1(H1)
5.d X=CH2 refined with riding coordinates:
 C00X(H00I,H00J), C00Y(H00N,H00T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 1.1497(3) 1.3735(8) 1.4185(3) 0.0303(10) Uani 1 1 d . . . . .
O002 O 0.9911(3) 1.5262(9) 1.3620(3) 0.0380(11) Uani 1 1 d . . . . .
O003 O 1.2988(3) 1.2987(8) 1.5979(3) 0.0374(11) Uani 1 1 d . . . . .
O004 O 1.4865(3) 1.7032(9) 1.6282(3) 0.0394(12) Uani 1 1 d . . . . .
O005 O 0.8974(4) 0.5201(10) 1.0262(3) 0.0460(12) Uani 1 1 d . . . . .
O006 O 1.6416(3) 1.5324(10) 1.6815(3) 0.0466(13) Uani 1 1 d . . . . .
O007 O 1.0557(4) 0.4424(9) 1.0743(3) 0.0484(14) Uani 1 1 d . . . . .
N008 N 0.9843(5) 0.5648(11) 1.0779(3) 0.0372(14) Uani 1 1 d . . . . .
O009 O 1.7279(4) 2.3195(13) 2.0620(3) 0.0682(17) Uani 1 1 d . . . . .
C00A C 0.9245(5) 0.9142(13) 1.1546(4) 0.0307(15) Uani 1 1 d . . . . .
H00A H 0.858896 0.869968 1.113700 0.037 Uiso 1 1 calc R . . . .
C00B C 1.0549(4) 1.3755(13) 1.3570(4) 0.0263(15) Uani 1 1 d . . . . .
C00C C 1.0398(5) 1.1689(13) 1.2836(4) 0.0260(15) Uani 1 1 d . . . . .
C00D C 1.0043(5) 0.7817(13) 1.1489(4) 0.0279(15) Uani 1 1 d . . . . .
N00E N 1.6527(5) 2.3685(15) 1.9960(4) 0.0520(17) Uani 1 1 d . . . . .
C00F C 0.9426(5) 1.1152(13) 1.2222(4) 0.0336(17) Uani 1 1 d . . . . .
H00F H 0.889129 1.215522 1.226620 0.040 Uiso 1 1 calc R . . . .
O00G O 1.5909(4) 2.5555(13) 1.9916(4) 0.0736(18) Uani 1 1 d . . . . .
C00H C 1.3487(4) 1.5480(14) 1.4963(4) 0.0342(16) Uani 1 1 d . . . . .
H00B H 1.343856 1.735794 1.466012 0.041 Uiso 1 1 calc R . . . .
H00C H 1.324412 1.394816 1.450512 0.041 Uiso 1 1 calc R . . . .
C00I C 1.5803(5) 1.6854(14) 1.6892(4) 0.0343(17) Uani 1 1 d . . . . .
C00J C 1.4564(5) 1.4887(14) 1.5575(4) 0.0351(16) Uani 1 1 d . . . . .
H00D H 1.463643 1.290767 1.582436 0.042 Uiso 1 1 calc R . . . .
H00E H 1.498084 1.504534 1.524379 0.042 Uiso 1 1 calc R . . . .
C00K C 1.2844(4) 1.5564(13) 1.5460(4) 0.0312(15) Uani 1 1 d . . . . .
H00K H 1.305148 1.725895 1.587258 0.037 Uiso 1 1 calc R . . . .
C00L C 1.6929(5) 1.8893(15) 1.8344(4) 0.0421(18) Uani 1 1 d . . . . .
H00L H 1.745392 1.788238 1.828420 0.051 Uiso 1 1 calc R . . . .
C00M C 1.1009(4) 0.8374(13) 1.2066(4) 0.0302(15) Uani 1 1 d . . . . .
H00M H 1.154022 0.745512 1.199235 0.036 Uiso 1 1 calc R . . . .
C00N C 1.5983(5) 1.8727(14) 1.7677(4) 0.0356(17) Uani 1 1 d . . . . .
C00O C 1.5407(5) 2.1922(15) 1.8492(5) 0.0448(19) Uani 1 1 d . . . . .
H00O H 1.489257 2.299590 1.854886 0.054 Uiso 1 1 calc R . . . .
C00P C 1.1185(5) 1.0281(13) 1.2747(4) 0.0298(15) Uani 1 1 d . . . . .
H00P H 1.184493 1.065008 1.316143 0.036 Uiso 1 1 calc R . . . .
C00Q C 1.5220(5) 2.0277(15) 1.7747(4) 0.0407(17) Uani 1 1 d . . . . .
H00Q H 1.457291 2.020341 1.728448 0.049 Uiso 1 1 calc R . . . .
C00R C 1.7117(5) 2.0512(16) 1.9094(4) 0.0419(18) Uani 1 1 d . . . . .
H00R H 1.776271 2.060070 1.955902 0.050 Uiso 1 1 calc R . . . .
C00S C 1.1728(4) 1.5724(13) 1.4924(4) 0.0312(15) Uani 1 1 d . . . . .
H00S H 1.149986 1.774133 1.472192 0.037 Uiso 1 1 calc R . . . .
C00T C 1.1344(5) 1.4617(14) 1.5590(4) 0.0364(17) Uani 1 1 d . . . . .
H00G H 1.074894 1.339974 1.528981 0.044 Uiso 1 1 calc R . . . .
H00H H 1.117227 1.625910 1.588221 0.044 Uiso 1 1 calc R . . . .
C00U C 1.6352(5) 2.1983(16) 1.9152(4) 0.0388(17) Uani 1 1 d . . . . .
C00V C 1.2192(5) 1.2821(16) 1.6271(4) 0.0435(18) Uani 1 1 d . . . . .
H00V H 1.195316 1.077523 1.614071 0.052 Uiso 0.52(4) 1 calc R . P A 2
C00W C 1.2654(13) 1.440(4) 1.7174(9) 0.026(5) Uani 0.48(4) 1 d D U P A 1
H00W H 1.284135 1.638113 1.720620 0.031 Uiso 0.48(4) 1 calc R . P A 1
C00X C 1.2793(9) 1.284(3) 1.7952(8) 0.041(5) Uani 0.560(18) 1 d D U P A 1
H00I H 1.260309 1.085970 1.791216 0.049 Uiso 0.560(18) 1 calc R . P A 1
H00J H 1.307565 1.377078 1.851200 0.049 Uiso 0.560(18) 1 calc R . P A 1
C1 C 1.2398(17) 1.318(6) 1.7176(12) 0.064(7) Uani 0.52(4) 1 d . U P A 2
H1 H 1.200205 1.221927 1.741745 0.077 Uiso 0.52(4) 1 calc R . P A 2
C00Y C 1.3100(15) 1.475(4) 1.7661(15) 0.062(7) Uani 0.440(18) 1 d . U P A 2
H00N H 1.349692 1.571646 1.742183 0.075 Uiso 0.440(18) 1 calc R . P A 2
H00T H 1.323536 1.498746 1.826885 0.075 Uiso 0.440(18) 1 calc R . P A 2


_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
O001 C00B 1.354(7) . ?
O001 C00S 1.455(7) . ?
O002 C00B 1.207(7) . ?
O003 C00K 1.431(7) . ?
O003 C00V 1.460(7) . ?
O004 C00I 1.342(7) . ?
O004 C00J 1.457(7) . ?
O005 N008 1.235(6) . ?
O006 C00I 1.202(7) . ?
O007 N008 1.227(7) . ?
N008 C00D 1.481(8) . ?
O009 N00E 1.217(7) . ?
C00A H00A 0.9500 . ?
C00A C00D 1.375(8) . ?
C00A C00F 1.394(8) . ?
C00B C00C 1.490(8) . ?
C00C C00F 1.401(8) . ?
C00C C00P 1.401(8) . ?
C00D C00M 1.378(8) . ?
N00E O00G 1.240(8) . ?
N00E C00U 1.482(9) . ?
C00F H00F 0.9500 . ?
C00H H00B 0.9900 . ?
C00H H00C 0.9900 . ?
C00H C00J 1.522(8) . ?
C00H C00K 1.504(8) . ?
C00I C00N 1.493(9) . ?
C00J H00D 0.9900 . ?
C00J H00E 0.9900 . ?
C00K H00K 1.0000 . ?
C00K C00S 1.524(8) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.383(9) . ?
C00L C00R 1.379(9) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.370(8) . ?
C00N C00Q 1.388(8) . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.378(9) . ?
C00O C00U 1.376(9) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?
C00R C00U 1.363(9) . ?
C00S H00S 1.0000 . ?
C00S C00T 1.531(8) . ?
C00T H00G 0.9900 . ?
C00T H00H 0.9900 . ?
C00T C00V 1.539(8) . ?
C00V H00V 1.0000 . ?
C00V C00W 1.547(19) . ?
C00V C1 1.414(18) . ?
C00W H00W 0.9500 . ?
C00W C00X 1.419(19) . ?
C00X H00I 0.9500 . ?
C00X H00J 0.9500 . ?
C1 H1 0.9500 . ?
C1 C00Y 1.25(4) . ?
C00Y H00N 0.9500 . ?
C00Y H00T 0.9500 . ?

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
C00B O001 C00S 115.9(4) . . ?
C00K O003 C00V 107.9(5) . . ?
C00I O004 C00J 116.1(5) . . ?
O005 N008 C00D 118.1(5) . . ?
O007 N008 O005 124.5(6) . . ?
O007 N008 C00D 117.4(6) . . ?
C00D C00A H00A 121.0 . . ?
C00D C00A C00F 118.1(6) . . ?
C00F C00A H00A 121.0 . . ?
O001 C00B C00C 111.5(5) . . ?
O002 C00B O001 123.6(6) . . ?
O002 C00B C00C 124.9(6) . . ?
C00F C00C C00B 117.8(5) . . ?
C00F C00C C00P 119.8(6) . . ?
C00P C00C C00B 122.4(6) . . ?
C00A C00D N008 117.7(6) . . ?
C00A C00D C00M 123.3(6) . . ?
C00M C00D N008 119.0(6) . . ?
O009 N00E O00G 124.3(7) . . ?
O009 N00E C00U 117.7(6) . . ?
O00G N00E C00U 118.0(6) . . ?
C00A C00F C00C 119.8(6) . . ?
C00A C00F H00F 120.1 . . ?
C00C C00F H00F 120.1 . . ?
H00B C00H H00C 107.9 . . ?
C00J C00H H00B 109.2 . . ?
C00J C00H H00C 109.2 . . ?
C00K C00H H00B 109.2 . . ?
C00K C00H H00C 109.2 . . ?
C00K C00H C00J 111.8(5) . . ?
O004 C00I C00N 112.0(6) . . ?
O006 C00I O004 123.5(6) . . ?
O006 C00I C00N 124.5(6) . . ?
O004 C00J C00H 107.5(5) . . ?
O004 C00J H00D 110.2 . . ?
O004 C00J H00E 110.2 . . ?
C00H C00J H00D 110.2 . . ?
C00H C00J H00E 110.2 . . ?
H00D C00J H00E 108.5 . . ?
O003 C00K C00H 109.9(5) . . ?
O003 C00K H00K 108.2 . . ?
O003 C00K C00S 104.1(5) . . ?
C00H C00K H00K 108.2 . . ?
C00H C00K C00S 117.9(5) . . ?
C00S C00K H00K 108.2 . . ?
C00N C00L H00L 119.7 . . ?
C00R C00L H00L 119.7 . . ?
C00R C00L C00N 120.6(7) . . ?
C00D C00M H00M 120.7 . . ?
C00P C00M C00D 118.6(6) . . ?
C00P C00M H00M 120.7 . . ?
C00L C00N C00I 118.9(6) . . ?
C00L C00N C00Q 119.9(7) . . ?
C00Q C00N C00I 121.2(6) . . ?
C00Q C00O H00O 120.6 . . ?
C00U C00O H00O 120.6 . . ?
C00U C00O C00Q 118.9(7) . . ?
C00C C00P H00P 119.8 . . ?
C00M C00P C00C 120.3(6) . . ?
C00M C00P H00P 119.8 . . ?
C00N C00Q H00Q 120.2 . . ?
C00O C00Q C00N 119.7(6) . . ?
C00O C00Q H00Q 120.2 . . ?
C00L C00R H00R 120.8 . . ?
C00U C00R C00L 118.3(7) . . ?
C00U C00R H00R 120.8 . . ?
O001 C00S C00K 106.2(5) . . ?
O001 C00S H00S 112.1 . . ?
O001 C00S C00T 111.9(5) . . ?
C00K C00S H00S 112.1 . . ?
C00K C00S C00T 101.9(5) . . ?
C00T C00S H00S 112.1 . . ?
C00S C00T H00G 110.6 . . ?
C00S C00T H00H 110.6 . . ?
C00S C00T C00V 105.8(5) . . ?
H00G C00T H00H 108.7 . . ?
C00V C00T H00G 110.6 . . ?
C00V C00T H00H 110.6 . . ?
C00O C00U N00E 117.8(6) . . ?
C00R C00U N00E 119.5(6) . . ?
C00R C00U C00O 122.6(7) . . ?
O003 C00V C00T 104.9(5) . . ?
O003 C00V H00V 103.9 . . ?
O003 C00V C00W 101.8(8) . . ?
C00T C00V H00V 103.9 . . ?
C00T C00V C00W 110.8(7) . . ?
C1 C00V O003 120.2(13) . . ?
C1 C00V C00T 117.9(9) . . ?
C1 C00V H00V 103.9 . . ?
C00V C00W H00W 120.6 . . ?
C00X C00W C00V 118.7(16) . . ?
C00X C00W H00W 120.6 . . ?
C00W C00X H00I 120.0 . . ?
C00W C00X H00J 120.0 . . ?
H00I C00X H00J 120.0 . . ?
C00V C1 H1 119.8 . . ?
C00Y C1 C00V 120(3) . . ?
C00Y C1 H1 119.8 . . ?
C1 C00Y H00N 120.0 . . ?
C1 C00Y H00T 120.0 . . ?
H00N C00Y H00T 120.0 . . ?

_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
;
####################################################################### 
# 
# 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_raf-ram-061_mo
_database_code_depnum_ccdc_archive 'CCDC 2190737'
loop_
_audit_author_name
_audit_author_address
'Mhatre D.S.'
;Indian institute of technology Bombay Powai Mumbai
India
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
darshansmhatre@chem.iitb.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N2 O9'
_chemical_formula_sum            'C22 H21 N2 O9'
_chemical_formula_weight         457.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0311(7)
_cell_length_b                   41.153(3)
_cell_length_c                   7.9883(11)
_cell_angle_alpha                90
_cell_angle_beta                 112.911(14)
_cell_angle_gamma                90
_cell_volume                     2129.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.8410
_cell_measurement_theta_min      2.8060
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8643
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.979
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   1.00   16.00    --  -20.00   0.00-108.00  180
  2  ω   -107.00 -72.00   1.00   16.00    --  -20.00 -72.00-180.00   35
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1844
_reflns_number_total             3679
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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         0.522
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0849
_refine_ls_restrained_S_all      1.011
_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)+(0.1575P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.3167
_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 Ternary CH refined with riding coordinates:
 C00L(H00L), C00T(H00T), C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00R(H00D,H00E), C00S(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00W(H00W), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C00V(H00J,H00K,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.4736(5) 0.57769(8) 0.5297(5) 0.0278(10) Uani 1 1 d . . . . .
O002 O 0.2888(6) 0.60068(9) 0.0855(5) 0.0302(10) Uani 1 1 d . . . . .
O003 O 0.1524(5) 0.66956(8) 0.1001(5) 0.0284(10) Uani 1 1 d . . . . .
O004 O 0.7767(6) 0.55098(9) 0.6336(6) 0.0374(11) Uani 1 1 d . . . . .
O005 O -0.1357(6) 0.69804(10) 0.0573(7) 0.0473(13) Uani 1 1 d . . . . .
O006 O 0.6529(7) 0.80424(10) -0.0139(7) 0.0474(13) Uani 1 1 d . . . . .
O007 O 0.3876(7) 0.83392(10) -0.0458(7) 0.0466(12) Uani 1 1 d . . . . .
O008 O 0.0250(7) 0.46025(10) 0.8595(7) 0.0542(14) Uani 1 1 d . . . . .
N009 N 0.1934(7) 0.45446(12) 0.8539(7) 0.0340(13) Uani 1 1 d . . . . .
N00A N 0.4774(8) 0.80766(12) -0.0200(7) 0.0379(13) Uani 1 1 d . . . . .
O00B O 0.2766(7) 0.42817(11) 0.8977(8) 0.0609(16) Uani 1 1 d . . . . .
C00C C 0.4970(8) 0.47499(13) 0.8113(8) 0.0255(13) Uani 1 1 d . . . . .
H00C H 0.566947 0.455301 0.860501 0.031 Uiso 1 1 calc R . . . .
C00D C 0.5990(9) 0.55299(13) 0.6144(8) 0.0269(13) Uani 1 1 d . . . . .
C00E C 0.0401(9) 0.69681(13) 0.0695(9) 0.0337(15) Uani 1 1 d . . . . .
C00F C 0.2965(8) 0.48021(13) 0.7952(8) 0.0277(13) Uani 1 1 d . . . . .
C00G C 0.2840(8) 0.53232(13) 0.6634(8) 0.0274(14) Uani 1 1 d . . . . .
H00G H 0.211921 0.551704 0.611234 0.033 Uiso 1 1 calc R . . . .
C00H C 0.1593(8) 0.72533(13) 0.0491(8) 0.0285(14) Uani 1 1 d . . . . .
C00I C 0.5928(8) 0.49938(13) 0.7535(8) 0.0286(14) Uani 1 1 d . . . . .
H00I H 0.731283 0.496703 0.764180 0.034 Uiso 1 1 calc R . . . .
C00J C 0.3692(9) 0.77872(13) 0.0067(8) 0.0298(14) Uani 1 1 d . . . . .
C00K C 0.4860(8) 0.52786(13) 0.6797(8) 0.0263(13) Uani 1 1 d . . . . .
C00L C 0.0509(8) 0.63906(13) 0.1101(8) 0.0288(14) Uani 1 1 d . . . . .
H00L H -0.054344 0.641901 0.164476 0.035 Uiso 1 1 calc R . . . .
C00M C 0.1843(9) 0.78355(14) 0.0276(9) 0.0386(17) Uani 1 1 d . . . . .
H00M H 0.131503 0.804799 0.027567 0.046 Uiso 1 1 calc R . . . .
C00N C 0.1883(8) 0.50833(14) 0.7238(8) 0.0320(15) Uani 1 1 d . . . . .
H00N H 0.051139 0.511141 0.716337 0.038 Uiso 1 1 calc R . . . .
C00O C 0.2444(9) 0.62541(16) -0.2010(9) 0.0419(17) Uani 1 1 d . . . . .
H00O H 0.165991 0.628770 -0.326824 0.050 Uiso 1 1 calc R . . . .
C00P C 0.0795(8) 0.75646(14) 0.0484(9) 0.0378(16) Uani 1 1 d . . . . .
H00P H -0.047866 0.759012 0.062310 0.045 Uiso 1 1 calc R . . . .
C00Q C 0.5661(9) 0.60279(12) 0.4582(8) 0.0296(14) Uani 1 1 d . . . . .
H00A H 0.614560 0.593512 0.367417 0.035 Uiso 1 1 calc R . . . .
H00B H 0.685428 0.612704 0.557373 0.035 Uiso 1 1 calc R . . . .
C00R C -0.0403(8) 0.62425(13) -0.0795(8) 0.0281(14) Uani 1 1 d . . . . .
H00D H -0.096725 0.641300 -0.173369 0.034 Uiso 1 1 calc R . . . .
H00E H -0.151413 0.608596 -0.090257 0.034 Uiso 1 1 calc R . . . .
C00S C 0.4003(8) 0.62793(12) 0.3707(8) 0.0269(13) Uani 1 1 d . . . . .
H00F H 0.353238 0.636572 0.463801 0.032 Uiso 1 1 calc R . . . .
H00H H 0.460872 0.646204 0.327590 0.032 Uiso 1 1 calc R . . . .
C00T C 0.1471(8) 0.60674(15) -0.0984(8) 0.0332(15) Uani 1 1 d . . . . .
H00T H 0.099264 0.585415 -0.160638 0.040 Uiso 1 1 calc R . . . .
C00U C 0.2166(8) 0.61519(13) 0.2139(8) 0.0267(13) Uani 1 1 d . . . . .
H00U H 0.151670 0.597705 0.260858 0.032 Uiso 1 1 calc R . . . .
C00V C 0.4337(9) 0.63795(16) -0.1312(9) 0.0430(17) Uani 1 1 d . . . . .
H00J H 0.508675 0.631902 -0.207463 0.064 Uiso 1 1 calc GR . . . .
H00K H 0.507226 0.629514 -0.008006 0.064 Uiso 1 1 calc GR . . . .
H00Q H 0.424719 0.661680 -0.126831 0.064 Uiso 1 1 calc GR . . . .
C00W C 0.3485(9) 0.72170(14) 0.0292(9) 0.0355(16) Uani 1 1 d . . . . .
H00W H 0.403467 0.700610 0.029209 0.043 Uiso 1 1 calc R . . . .
C00X C 0.4538(8) 0.74865(14) 0.0096(8) 0.0338(15) Uani 1 1 d . . . . .
H00X H 0.582795 0.746434 -0.001589 0.041 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00D 1.343(6) . ?
O001 C00Q 1.451(6) . ?
O002 C00T 1.440(7) . ?
O002 C00U 1.440(6) . ?
O003 C00E 1.338(6) . ?
O003 C00L 1.462(6) . ?
O004 C00D 1.201(6) . ?
O005 C00E 1.202(7) . ?
O006 N00A 1.224(6) . ?
O007 N00A 1.228(6) . ?
O008 N009 1.226(6) . ?
N009 O00B 1.215(6) . ?
N009 C00F 1.461(7) . ?
N00A C00J 1.472(7) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.382(7) . ?
C00C C00I 1.384(7) . ?
C00D C00K 1.515(8) . ?
C00E C00H 1.488(8) . ?
C00F C00N 1.380(7) . ?
C00G H00G 0.9500 . ?
C00G C00K 1.387(7) . ?
C00G C00N 1.383(7) . ?
C00H C00P 1.398(7) . ?
C00H C00W 1.408(8) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.393(7) . ?
C00J C00M 1.388(8) . ?
C00J C00X 1.369(7) . ?
C00L H00L 1.0000 . ?
C00L C00R 1.523(8) . ?
C00L C00U 1.503(7) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.382(8) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00T 1.472(8) . ?
C00O C00V 1.331(8) . ?
C00P H00P 0.9500 . ?
C00Q H00A 0.9900 . ?
C00Q H00B 0.9900 . ?
C00Q C00S 1.511(7) . ?
C00R H00D 0.9900 . ?
C00R H00E 0.9900 . ?
C00R C00T 1.560(8) . ?
C00S H00F 0.9900 . ?
C00S H00H 0.9900 . ?
C00S C00U 1.501(8) . ?
C00T H00T 1.0000 . ?
C00U H00U 1.0000 . ?
C00V H00J 0.9800 . ?
C00V H00K 0.9800 . ?
C00V H00Q 0.9800 . ?
C00W H00W 0.9500 . ?
C00W C00X 1.376(8) . ?
C00X H00X 0.9500 . ?

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
C00D O001 C00Q 115.5(4) . . ?
C00U O002 C00T 111.0(4) . . ?
C00E O003 C00L 117.6(4) . . ?
O008 N009 C00F 118.6(5) . . ?
O00B N009 O008 121.8(5) . . ?
O00B N009 C00F 119.6(5) . . ?
O006 N00A O007 123.5(5) . . ?
O006 N00A C00J 118.1(5) . . ?
O007 N00A C00J 118.4(5) . . ?
C00F C00C H00C 121.1 . . ?
C00F C00C C00I 117.9(5) . . ?
C00I C00C H00C 121.1 . . ?
O001 C00D C00K 111.1(5) . . ?
O004 C00D O001 124.2(5) . . ?
O004 C00D C00K 124.6(5) . . ?
O003 C00E C00H 111.3(5) . . ?
O005 C00E O003 124.4(5) . . ?
O005 C00E C00H 124.3(5) . . ?
C00C C00F N009 118.3(5) . . ?
C00N C00F N009 118.6(5) . . ?
C00N C00F C00C 123.2(5) . . ?
C00K C00G H00G 120.3 . . ?
C00N C00G H00G 120.3 . . ?
C00N C00G C00K 119.5(5) . . ?
C00P C00H C00E 118.8(5) . . ?
C00P C00H C00W 119.5(5) . . ?
C00W C00H C00E 121.7(5) . . ?
C00C C00I H00I 120.0 . . ?
C00C C00I C00K 119.9(5) . . ?
C00K C00I H00I 120.0 . . ?
C00M C00J N00A 117.5(5) . . ?
C00X C00J N00A 119.2(5) . . ?
C00X C00J C00M 123.2(5) . . ?
C00G C00K C00D 122.2(5) . . ?
C00G C00K C00I 121.0(5) . . ?
C00I C00K C00D 116.8(5) . . ?
O003 C00L H00L 112.5 . . ?
O003 C00L C00R 108.4(4) . . ?
O003 C00L C00U 107.5(4) . . ?
C00R C00L H00L 112.5 . . ?
C00U C00L H00L 112.5 . . ?
C00U C00L C00R 102.9(5) . . ?
C00J C00M H00M 121.1 . . ?
C00P C00M C00J 117.9(5) . . ?
C00P C00M H00M 121.1 . . ?
C00F C00N C00G 118.6(5) . . ?
C00F C00N H00N 120.7 . . ?
C00G C00N H00N 120.7 . . ?
C00T C00O H00O 117.4 . . ?
C00V C00O H00O 117.4 . . ?
C00V C00O C00T 125.1(6) . . ?
C00H C00P H00P 119.7 . . ?
C00M C00P C00H 120.5(5) . . ?
C00M C00P H00P 119.7 . . ?
O001 C00Q H00A 110.4 . . ?
O001 C00Q H00B 110.4 . . ?
O001 C00Q C00S 106.6(4) . . ?
H00A C00Q H00B 108.6 . . ?
C00S C00Q H00A 110.4 . . ?
C00S C00Q H00B 110.4 . . ?
C00L C00R H00D 111.0 . . ?
C00L C00R H00E 111.0 . . ?
C00L C00R C00T 103.7(4) . . ?
H00D C00R H00E 109.0 . . ?
C00T C00R H00D 111.0 . . ?
C00T C00R H00E 111.0 . . ?
C00Q C00S H00F 108.8 . . ?
C00Q C00S H00H 108.8 . . ?
H00F C00S H00H 107.7 . . ?
C00U C00S C00Q 113.9(4) . . ?
C00U C00S H00F 108.8 . . ?
C00U C00S H00H 108.8 . . ?
O002 C00T C00O 111.8(5) . . ?
O002 C00T C00R 104.9(4) . . ?
O002 C00T H00T 108.7 . . ?
C00O C00T C00R 114.0(5) . . ?
C00O C00T H00T 108.7 . . ?
C00R C00T H00T 108.7 . . ?
O002 C00U C00L 106.9(5) . . ?
O002 C00U C00S 108.2(4) . . ?
O002 C00U H00U 108.0 . . ?
C00L C00U H00U 108.0 . . ?
C00S C00U C00L 117.6(5) . . ?
C00S C00U H00U 108.0 . . ?
C00O C00V H00J 109.5 . . ?
C00O C00V H00K 109.5 . . ?
C00O C00V H00Q 109.5 . . ?
H00J C00V H00K 109.5 . . ?
H00J C00V H00Q 109.5 . . ?
H00K C00V H00Q 109.5 . . ?
C00H C00W H00W 120.0 . . ?
C00X C00W C00H 120.1(5) . . ?
C00X C00W H00W 120.0 . . ?
C00J C00X C00W 118.8(5) . . ?
C00J C00X H00X 120.6 . . ?
C00W C00X H00X 120.6 . . ?

_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
;
