# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_pm-ss-396r
_database_code_depnum_ccdc_archive 'CCDC 2064075'
loop_
_audit_author_name
_audit_author_address
'Sudip sau'
;NISER
India
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        7-Iodo-3-nitro-4-phenyl-2H-chromen-2-one
_chemical_formula_moiety         'C15 H8 I N O4'
_chemical_formula_sum            'C16 H8 I N0.25 O4'
_chemical_formula_weight         394.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H8 I N O4 '
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'
I I -0.3257 6.8362 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.34430(10)
_cell_length_b                   15.20400(10)
_cell_length_c                   8.99570(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.7960(10)
_cell_angle_gamma                90
_cell_volume                     1389.75(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16773
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.0450
_cell_measurement_theta_min      4.3260
_shelx_estimated_absorpt_T_max   0.138
_shelx_estimated_absorpt_T_min   0.121
_exptl_absorpt_coefficient_mu    18.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             763
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20661
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.189
_diffrn_reflns_theta_min         4.351
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -28.00   0.50    0.50    --  -38.50 -55.00 -88.00  146
  2  ω    -49.00  25.00   0.50    0.50    --  -38.50  55.00  54.00  148
  3  ω     38.00 112.00   0.50    0.50    --   48.56  55.00  54.00  148
  4  ω    -14.00  59.00   0.50    0.50    --   48.56 -55.00 -88.00  146
  5  ω     91.00 165.00   0.50    2.60    --  101.38  55.00  54.00  148
  6  ω     38.00 112.00   0.50    2.60    --  101.38 -55.00 -88.00  148
  7  ω   -101.00 -22.00   0.50    0.50    --  -38.50 -66.00  70.49  158
  8  ω    -50.00  24.00   0.50    0.50    --  -38.50  57.00-180.00  148
  9  ω    -86.00  -6.00   0.50    0.50    --  -38.50 125.00-180.00  160
 10  ω     28.00 100.00   0.50    0.50    --   48.56-125.00 120.00  144
 11  ω     37.00 106.00   0.50    2.60    --  101.38 -45.00  30.00  138
 12  ω     88.00 164.00   0.50    2.60    --  101.38  61.00  30.00  152
 13  ω     32.00 109.00   0.50    2.60    --  101.38-111.00 120.00  154
 14  ω     33.00 110.00   0.50    2.60    --  101.38 -15.00-150.00  154
 15  ω     33.00 105.00   0.50    2.60    --  101.38 -30.00-180.00  144
 16  ω    103.00 166.00   0.50    2.60    --  101.38  77.00 -30.00  126
 17  ω     37.00 125.00   0.50    2.60    --  101.38 -77.00 -90.00  176
 18  ω     33.00 107.00   0.50    2.60    --  101.38 -94.00 -90.00  148
 19  ω     32.00 109.00   0.50    2.60    --  101.38-111.00  60.00  154
 20  ω     37.00 125.00   0.50    2.60    --  101.38 -77.00 150.00  176
 21  ω    104.00 171.00   0.50    2.60    --  101.38 111.00-180.00  134
 22  ω     32.00 109.00   0.50    2.60    --  101.38-111.00-150.00  154
 23  ω     33.00 107.00   0.50    2.60    --  101.38 -94.00 150.00  148
 24  ω     93.00 170.00   0.50    2.60    --  101.38  15.00 -30.00  154
 25  ω    104.00 171.00   0.50    2.60    --  101.38 111.00 -30.00  134
 26  ω     37.00 106.00   0.50    2.60    --  101.38 -45.00 -60.00  138
 27  ω    103.00 166.00   0.50    2.60    --  101.38  77.00-120.00  126
 28  ω    104.00 171.00   0.50    2.60    --  101.38 111.00 -90.00  134
 29  ω     45.00 115.00   0.50    0.50    --   48.56  37.00 -90.00  140
 30  ω     37.00 112.00   0.50    0.50    --   48.56  57.00   0.00  150
 31  ω     37.00 108.00   0.50    0.50    --   48.56  57.00 120.00  142
 32  ω     37.00 112.00   0.50    0.50    --   48.56  57.00-180.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0680793000
_diffrn_orient_matrix_UB_12      -0.0644502000
_diffrn_orient_matrix_UB_13      -0.1220453000
_diffrn_orient_matrix_UB_21      -0.1335754000
_diffrn_orient_matrix_UB_22      0.0198723000
_diffrn_orient_matrix_UB_23      0.0449387000
_diffrn_orient_matrix_UB_31      -0.0228494000
_diffrn_orient_matrix_UB_32      0.0756226000
_diffrn_orient_matrix_UB_33      -0.1160366000
_diffrn_oxdiff_digest_frames     
;
017f1221ae1281ae2c2c3824223ebaa89f0004217c0
;
_diffrn_oxdiff_digest_hkl        
;
0169d2081b34db966994194f654b0619ae6eb1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2796
_reflns_number_total             2838
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.963
_refine_diff_density_min         -1.827
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+1.6887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
;
_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
I001 I 0.21094(2) 0.67308(2) 1.00776(2) 0.02228(10) Uani 1 1 d . . . . .
O002 O 0.5800(2) 0.82216(11) 0.7452(2) 0.0168(4) Uani 1 1 d . . . . .
O003 O 0.7219(2) 0.89842(12) 0.6400(2) 0.0217(4) Uani 1 1 d . . . . .
O004 O 0.8601(2) 0.71867(14) 0.4536(2) 0.0237(4) Uani 1 1 d . . . . .
O005 O 0.9561(2) 0.79206(15) 0.6505(2) 0.0275(5) Uani 1 1 d . . . . .
N006 N 0.8638(2) 0.75199(14) 0.5780(2) 0.0158(4) Uani 1 1 d . . . . .
C007 C 0.6866(3) 0.82759(15) 0.6755(3) 0.0164(6) Uani 1 1 d . . . . .
C008 C 0.5872(3) 0.66221(17) 0.7516(3) 0.0150(5) Uani 1 1 d . . . . .
C009 C 0.4271(3) 0.74716(17) 0.8598(3) 0.0159(5) Uani 1 1 d . . . . .
H009 H 0.3928 0.8012 0.8818 0.019 Uiso 1 1 calc R . . . .
C00A C 0.5321(3) 0.58454(17) 0.7977(3) 0.0179(5) Uani 1 1 d . . . . .
H00A H 0.5680 0.5305 0.7792 0.021 Uiso 1 1 calc R . . . .
C00B C 0.7448(3) 0.74343(18) 0.6453(3) 0.0150(5) Uani 1 1 d . . . . .
C00C C 0.5325(3) 0.74243(17) 0.7858(3) 0.0155(5) Uani 1 1 d . . . . .
C00D C 0.7117(3) 0.52274(18) 0.5373(3) 0.0207(6) Uani 1 1 d . . . . .
H00D H 0.6301 0.5354 0.4782 0.025 Uiso 1 1 calc R . . . .
C00E C 0.7682(3) 0.58043(17) 0.6500(3) 0.0156(5) Uani 1 1 d . . . . .
C00F C 0.7006(3) 0.66364(16) 0.6786(3) 0.0148(5) Uani 1 1 d . . . . .
C00G C 0.3735(3) 0.66876(17) 0.9007(3) 0.0159(5) Uani 1 1 d . . . . .
C00H C 0.4257(3) 0.58737(18) 0.8700(3) 0.0191(5) Uani 1 1 d . . . . .
H00H H 0.3890 0.5355 0.8980 0.023 Uiso 1 1 calc R . . . .
C00I C 0.7779(3) 0.4451(2) 0.5125(3) 0.0238(6) Uani 1 1 d . . . . .
H00I H 0.7411 0.4063 0.4363 0.029 Uiso 1 1 calc R . . . .
C00J C 0.8987(3) 0.42710(18) 0.6029(3) 0.0234(6) Uani 1 1 d . . . . .
H00J H 0.9422 0.3752 0.5881 0.028 Uiso 1 1 calc R . . . .
C00K C 0.8906(3) 0.56245(18) 0.7391(3) 0.0215(6) Uani 1 1 d . . . . .
H00K H 0.9285 0.6017 0.8140 0.026 Uiso 1 1 calc R . . . .
C00L C 0.9558(3) 0.48498(19) 0.7149(4) 0.0255(6) Uani 1 1 d . . . . .
H00L H 1.0375 0.4722 0.7739 0.031 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
I001 C00G 2.090(3) . ?
O002 C007 1.369(4) . ?
O002 C00C 1.382(3) . ?
O003 C007 1.199(3) . ?
O004 N006 1.223(3) . ?
O005 N006 1.215(3) . ?
N006 C00B 1.476(4) . ?
C007 C00B 1.461(4) . ?
C008 C00A 1.407(4) . ?
C008 C00C 1.402(4) . ?
C008 C00F 1.448(4) . ?
C009 H009 0.9300 . ?
C009 C00C 1.383(4) . ?
C009 C00G 1.392(4) . ?
C00A H00A 0.9300 . ?
C00A C00H 1.380(4) . ?
C00B C00F 1.350(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.384(4) . ?
C00D C00I 1.403(4) . ?
C00E C00F 1.491(4) . ?
C00E C00K 1.394(4) . ?
C00G C00H 1.398(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.385(4) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.384(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.394(4) . ?
C00L H00L 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O002 C00C 122.0(2) . . ?
O004 N006 C00B 116.9(2) . . ?
O005 N006 O004 125.9(2) . . ?
O005 N006 C00B 117.2(2) . . ?
O002 C007 C00B 115.3(2) . . ?
O003 C007 O002 119.2(2) . . ?
O003 C007 C00B 125.5(3) . . ?
C00A C008 C00F 123.6(2) . . ?
C00C C008 C00A 117.6(3) . . ?
C00C C008 C00F 118.7(2) . . ?
C00C C009 H009 120.9 . . ?
C00C C009 C00G 118.1(2) . . ?
C00G C009 H009 120.9 . . ?
C008 C00A H00A 119.5 . . ?
C00H C00A C008 121.0(3) . . ?
C00H C00A H00A 119.5 . . ?
C007 C00B N006 113.8(2) . . ?
C00F C00B N006 120.9(2) . . ?
C00F C00B C007 125.3(3) . . ?
O002 C00C C008 121.8(2) . . ?
O002 C00C C009 115.6(2) . . ?
C009 C00C C008 122.5(2) . . ?
C00E C00D H00D 120.1 . . ?
C00E C00D C00I 119.9(3) . . ?
C00I C00D H00D 120.1 . . ?
C00D C00E C00F 121.1(2) . . ?
C00D C00E C00K 120.7(2) . . ?
C00K C00E C00F 118.2(2) . . ?
C008 C00F C00E 120.8(2) . . ?
C00B C00F C008 116.8(2) . . ?
C00B C00F C00E 122.4(3) . . ?
C009 C00G I001 119.3(2) . . ?
C009 C00G C00H 121.2(3) . . ?
C00H C00G I001 119.5(2) . . ?
C00A C00H C00G 119.5(3) . . ?
C00A C00H H00H 120.3 . . ?
C00G C00H H00H 120.3 . . ?
C00D C00I H00I 120.5 . . ?
C00J C00I C00D 119.1(3) . . ?
C00J C00I H00I 120.5 . . ?
C00I C00J H00J 119.4 . . ?
C00L C00J C00I 121.2(3) . . ?
C00L C00J H00J 119.4 . . ?
C00E C00K H00K 120.3 . . ?
C00E C00K C00L 119.3(3) . . ?
C00L C00K H00K 120.3 . . ?
C00J C00L C00K 119.9(3) . . ?
C00J C00L H00L 120.1 . . ?
C00K C00L H00L 120.1 . . ?

_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 3.627
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_pm_ss_426
_database_code_depnum_ccdc_archive 'CCDC 2064074'
loop_
_audit_author_name
_audit_author_address
'Sudip sau'
;NISER
India
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        3-Nitro-4-(p-tolyl)-2H-chromen-2-one
_chemical_formula_moiety         'C16 H11 N O4'
_chemical_formula_sum            'C16 H11 N O4'
_chemical_formula_weight         281.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H11 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2983(8)
_cell_length_b                   9.1387(8)
_cell_length_c                   9.6145(7)
_cell_angle_alpha                73.544(7)
_cell_angle_beta                 72.349(8)
_cell_angle_gamma                82.099(8)
_cell_volume                     665.27(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    298.84(10)
_cell_measurement_theta_max      75.1180
_cell_measurement_theta_min      4.9500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9577
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.375
_diffrn_reflns_theta_min         4.994
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.84(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -29.00   0.50    0.98    --  -38.50 -54.00 129.00  146
  2  ω    -47.00  25.00   0.50    0.98    --  -38.50  54.00 -86.00  144
  3  ω     39.00 111.00   0.50    0.98    --   48.06  54.00 -86.00  144
  4  ω    -15.00  57.00   0.50    0.98    --   48.06 -54.00 129.00  144
  5  ω     38.00 111.00   0.50    3.59    --  101.38 -54.00 129.00  146
  6  ω     92.00 165.00   0.50    3.59    --  101.38  54.00 -86.00  146
  7  ω    -42.00  28.00   0.50    0.98    --  -38.50  37.00  60.00  140
  8  ω     42.00 118.00   0.50    0.98    --   48.06  19.00 -90.00  152
  9  ω    -15.00  60.00   0.50    0.98    --   48.06 -57.00-120.00  150
 10  ω    -15.00  60.00   0.50    0.98    --   48.06 -57.00-150.00  150
 11  ω     37.00 111.00   0.50    0.98    --   48.06  57.00   0.00  148
 12  ω    104.00 171.00   0.50    3.59    --  101.38 111.00  90.00  134
 13  ω     32.00 109.00   0.50    3.59    --  101.38-111.00 150.00  154
 14  ω    104.00 171.00   0.50    3.59    --  101.38 111.00-150.00  134
 15  ω     32.00 109.00   0.50    3.59    --  101.38-111.00-150.00  154
 16  ω     39.00 115.00   0.50    3.59    --  101.38 -61.00 -30.00  152
 17  ω     93.00 170.00   0.50    3.59    --  101.38  15.00  90.00  154
 18  ω     98.00 170.00   0.50    3.59    --  101.38  30.00-150.00  144
 19  ω     33.00 107.00   0.50    3.59    --  101.38 -94.00  60.00  148
 20  ω     32.00 109.00   0.50    3.59    --  101.38-110.00 -57.92  154
 21  ω     33.00 110.00   0.50    3.59    --  101.38 -15.00-120.00  154
 22  ω     37.00 106.00   0.50    3.59    --  101.38 -45.00-180.00  138
 23  ω     37.00 106.00   0.50    3.59    --  101.38 -45.00  60.00  138
 24  ω     97.00 166.00   0.50    3.59    --  101.38  45.00 150.00  138
 25  ω     32.00 109.00   0.50    3.59    --  101.38-111.00   0.00  154
 26  ω     97.00 166.00   0.50    3.59    --  101.38  45.00-180.00  138
 27  ω     33.00 107.00   0.50    3.59    --  101.38 -94.00-180.00  148
 28  ω     90.00 164.00   0.50    3.59    --  101.38  58.00 115.55  148
 29  ω     33.00 107.00   0.50    3.59    --  101.38 -94.00 -60.00  148
 30  ω    104.00 171.00   0.50    3.59    --  101.38 111.00 150.00  134
 31  ω     37.00 111.00   0.50    0.98    --   48.06  57.00 -30.00  148
 32  ω     37.00 111.00   0.50    0.98    --   48.06  57.00-180.00  148
 33  ω     37.00 111.00   0.50    0.98    --   48.06  57.00 120.00  148
 34  ω     37.00 111.00   0.50    0.98    --   48.06  57.00  60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1319959000
_diffrn_orient_matrix_UB_12      -0.0854637000
_diffrn_orient_matrix_UB_13      -0.1052000000
_diffrn_orient_matrix_UB_21      -0.1433601000
_diffrn_orient_matrix_UB_22      -0.0551174000
_diffrn_orient_matrix_UB_23      -0.0402627000
_diffrn_orient_matrix_UB_31      0.0100264000
_diffrn_orient_matrix_UB_32      0.1437148000
_diffrn_orient_matrix_UB_33      -0.1325456000
_diffrn_oxdiff_digest_frames     
;
0166230f020bdf0f9b3bd2e5a2929cf27100032864d
;
_diffrn_oxdiff_digest_hkl        
;
011cefd55da01ba2c11658ee59bf8c36d5c41d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2201
_reflns_number_total             2670
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (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         0.347
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0708
_refine_ls_restrained_S_all      1.052
_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)+(0.1280P)²+0.2539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H00C(0.071) H00D(0.071) H00F(0.074) H00G(0.071) H00H(0.076)
 H00I(0.085) H00J(0.084) H00K(0.091) H00A(0.114) H00B(0.114) H00E(0.114)
 Fixed X: H00C(0.351255) H00D(0.368562) H00F(0.592944) H00G(0.452339)
 H00H(0.576283) H00I(0.468414) H00J(-0.012741) H00K(0.23621) H00A(0.844765)
 H00B(0.794266) H00E(0.718452)
 Fixed Y: H00C(0.340138) H00D(0.228733) H00F(0.058279) H00G(0.505028)
 H00H(0.169114) H00I(0.717314) H00J(0.84673) H00K(0.888379) H00A(-0.003553)
 H00B(-0.005701) H00E(-0.121805)
 Fixed Z: H00C(0.497014) H00D(0.926372) H00F(0.870344) H00G(0.811737)
 H00H(0.442686) H00I(0.888347) H00J(0.887653) H00K(0.926917) H00A(0.649965)
 H00B(0.506126) H00E(0.660921)
;
_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
O001 O -0.0820(2) 0.6306(2) 0.8083(2) 0.0630(5) Uani 1 1 d . . . . .
O002 O -0.2423(2) 0.5024(3) 0.7444(3) 0.0795(6) Uani 1 1 d . . . . .
O003 O 0.0057(3) 0.1505(2) 0.7670(3) 0.0847(7) Uani 1 1 d . . . . .
N004 N 0.0053(3) 0.2768(3) 0.6815(3) 0.0612(6) Uani 1 1 d . . . . .
O005 O -0.0214(3) 0.3035(3) 0.5592(3) 0.0871(7) Uani 1 1 d . . . . .
C006 C 0.1901(3) 0.4147(3) 0.7515(2) 0.0482(5) Uani 1 1 d . . . . .
C007 C 0.3348(3) 0.3027(3) 0.7177(3) 0.0501(5) Uani 1 1 d . . . . .
C008 C 0.2083(3) 0.5448(3) 0.8034(2) 0.0501(5) Uani 1 1 d . . . . .
C009 C 0.0392(3) 0.4055(3) 0.7299(3) 0.0522(6) Uani 1 1 d . . . . .
C00A C 0.0704(3) 0.6492(3) 0.8290(3) 0.0553(6) Uani 1 1 d . . . . .
C00B C 0.6088(3) 0.0926(3) 0.6504(3) 0.0587(6) Uani 1 1 d . . . . .
C00C C 0.3992(3) 0.2834(3) 0.5729(3) 0.0595(6) Uani 1 1 d . . . . .
H00C H 0.351255 0.340138 0.497014 0.071 Uiso 1 1 calc R . . . .
C00D C 0.4097(3) 0.2169(3) 0.8286(3) 0.0589(6) Uani 1 1 d . . . . .
H00D H 0.368562 0.228733 0.926372 0.071 Uiso 1 1 calc R . . . .
C00E C -0.1067(3) 0.5119(3) 0.7588(3) 0.0579(6) Uani 1 1 d . . . . .
C00F C 0.5442(3) 0.1143(3) 0.7948(3) 0.0621(6) Uani 1 1 d . . . . .
H00F H 0.592944 0.058279 0.870344 0.074 Uiso 1 1 calc R . . . .
C00G C 0.3584(3) 0.5730(3) 0.8271(3) 0.0589(6) Uani 1 1 d . . . . .
H00G H 0.452339 0.505028 0.811737 0.071 Uiso 1 1 calc R . . . .
C00H C 0.5343(3) 0.1801(3) 0.5407(3) 0.0632(7) Uani 1 1 d . . . . .
H00H H 0.576283 0.169114 0.442686 0.076 Uiso 1 1 calc R . . . .
C00I C 0.3682(4) 0.6999(4) 0.8728(3) 0.0707(7) Uani 1 1 d . . . . .
H00I H 0.468414 0.717314 0.888347 0.085 Uiso 1 1 calc R . . . .
C00J C 0.0802(4) 0.7776(3) 0.8733(3) 0.0697(7) Uani 1 1 d . . . . .
H00J H -0.012741 0.846730 0.887653 0.084 Uiso 1 1 calc R . . . .
C00K C 0.2289(4) 0.8025(4) 0.8960(4) 0.0761(8) Uani 1 1 d . . . . .
H00K H 0.236210 0.888379 0.926917 0.091 Uiso 1 1 calc R . . . .
C00L C 0.7547(4) -0.0197(4) 0.6135(4) 0.0760(8) Uani 1 1 d . . . . .
H00A H 0.844765 -0.003553 0.649965 0.114 Uiso 1 1 calc GR . . . .
H00B H 0.794266 -0.005701 0.506126 0.114 Uiso 1 1 calc GR . . . .
H00E H 0.718452 -0.121805 0.660921 0.114 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
O001 C00A 1.379(3) . ?
O001 C00E 1.363(3) . ?
O002 C00E 1.192(3) . ?
O003 N004 1.213(3) . ?
N004 O005 1.213(3) . ?
N004 C009 1.469(3) . ?
C006 C007 1.486(3) . ?
C006 C008 1.455(3) . ?
C006 C009 1.347(3) . ?
C007 C00C 1.385(3) . ?
C007 C00D 1.390(3) . ?
C008 C00A 1.394(3) . ?
C008 C00G 1.401(3) . ?
C009 C00E 1.454(3) . ?
C00A C00J 1.376(4) . ?
C00B C00F 1.389(4) . ?
C00B C00H 1.384(4) . ?
C00B C00L 1.500(3) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.381(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.376(4) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00I 1.371(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.389(4) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.375(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00E 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
C00E O001 C00A 122.52(18) . . ?
O003 N004 C009 117.6(2) . . ?
O005 N004 O003 124.3(2) . . ?
O005 N004 C009 118.1(2) . . ?
C008 C006 C007 120.83(18) . . ?
C009 C006 C007 122.4(2) . . ?
C009 C006 C008 116.7(2) . . ?
C00C C007 C006 120.0(2) . . ?
C00C C007 C00D 118.5(2) . . ?
C00D C007 C006 121.4(2) . . ?
C00A C008 C006 118.7(2) . . ?
C00A C008 C00G 117.7(2) . . ?
C00G C008 C006 123.7(2) . . ?
C006 C009 N004 121.3(2) . . ?
C006 C009 C00E 125.2(2) . . ?
C00E C009 N004 113.40(19) . . ?
O001 C00A C008 121.6(2) . . ?
C00J C00A O001 116.5(2) . . ?
C00J C00A C008 121.9(2) . . ?
C00F C00B C00L 121.6(2) . . ?
C00H C00B C00F 117.3(2) . . ?
C00H C00B C00L 121.0(2) . . ?
C007 C00C H00C 119.9 . . ?
C00H C00C C007 120.3(2) . . ?
C00H C00C H00C 119.9 . . ?
C007 C00D H00D 119.8 . . ?
C00F C00D C007 120.5(2) . . ?
C00F C00D H00D 119.8 . . ?
O001 C00E C009 115.26(19) . . ?
O002 C00E O001 118.9(2) . . ?
O002 C00E C009 125.8(3) . . ?
C00B C00F H00F 119.2 . . ?
C00D C00F C00B 121.6(2) . . ?
C00D C00F H00F 119.2 . . ?
C008 C00G H00G 119.7 . . ?
C00I C00G C008 120.7(2) . . ?
C00I C00G H00G 119.7 . . ?
C00B C00H H00H 119.1 . . ?
C00C C00H C00B 121.8(2) . . ?
C00C C00H H00H 119.1 . . ?
C00G C00I H00I 119.9 . . ?
C00G C00I C00K 120.2(3) . . ?
C00K C00I H00I 119.9 . . ?
C00A C00J H00J 120.3 . . ?
C00K C00J C00A 119.3(3) . . ?
C00K C00J H00J 120.3 . . ?
C00I C00K H00K 119.9 . . ?
C00J C00K C00I 120.2(3) . . ?
C00J C00K H00K 119.9 . . ?
C00B C00L H00A 109.5 . . ?
C00B C00L H00B 109.5 . . ?
C00B C00L H00E 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00E 109.5 . . ?
H00B C00L H00E 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 1.858
_oxdiff_exptl_absorpt_empirical_full_min 0.477
####################################################################### 
# 
# 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_pm_ss_491
_database_code_depnum_ccdc_archive 'CCDC 2076536'
loop_
_audit_author_name
_audit_author_address
'Sudip Sau'
;Niser
India
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-08-10 downloaded from the CCDC.
;
_audit_creation_date             2021-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2015/1
_chemical_name_common            ?
_chemical_name_systematic        6-methoxy-3-nitro-4-phenyl-2H-chromen-2-one
_chemical_formula_moiety         'C16 H11 N O5'
_chemical_formula_sum            'C16 H11 N O5'
_chemical_formula_weight         297.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H48 O16 N1 '
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x+, y+, z+'
'-x+, -y+, z+1/2'
'x+1/2, -y+1/2, z+'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.91770(10)
_cell_length_b                   16.29580(10)
_cell_length_c                   10.82590(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1396.81(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25337
_cell_measurement_temperature    299.3(6)
_cell_measurement_theta_max      75.0470
_cell_measurement_theta_min      4.8770
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37735
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.564
_diffrn_reflns_theta_min         4.904
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.3(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  -2.00   0.50    1.50    --  -38.50 120.00 -87.00  164
  2  ω   -107.00 -22.00   0.50    1.50    --  -38.50 155.00  69.00  170
  3  ω     44.00 118.00   0.50    1.50    --   49.56-155.00  31.00  148
  4  ω     24.00  98.00   0.50    1.50    --   49.56-120.00-171.00  148
  5  ω     37.00 111.00   0.50    7.00    --  102.63-120.00-171.00  148
  6  ω     79.00 162.00   0.50    7.00    --  102.63 155.00  69.00  166
  7  ω    100.00 169.00   0.50    7.00    --  102.63 120.00 -87.00  138
  8  ω    -32.00   1.00   0.50    1.50    --   14.00 117.00  -4.44   66
  9  ω     -7.00  20.00   0.50    1.50    --   26.00  95.00 167.44   54
 10  ω     -5.00  24.00   0.50    1.50    --   26.00  91.00-113.18   58
 11  ω      2.00  31.00   0.50    1.50    --   30.00  86.00 101.90   58
 12  ω     -1.00  29.00   0.50    1.50    --   30.00  90.00  -3.04   60
 13  ω     14.00  42.00   0.50    1.50    --   38.00  79.00-167.30   56
 14  ω   -108.00 -33.00   0.50    1.50    --  -38.50 -19.00-180.00  150
 15  ω   -102.00 -21.00   0.50    1.50    --  -38.50 -70.00 -61.51  162
 16  ω     16.00  42.00   0.50    1.50    --   42.00  82.00 -52.74   52
 17  ω     16.00  42.00   0.50    1.50    --   42.00  82.00 -99.60   52
 18  ω     16.00  42.00   0.50    1.50    --   42.00  82.00  58.14   52
 19  ω     16.00  42.00   0.50    1.50    --   42.00  82.00 147.57   52
 20  ω     16.00  42.00   0.50    1.50    --   42.00  82.00-142.22   52
 21  ω     36.00 117.00   0.50    1.50    --   54.00  71.00 163.57  162
 22  ω     34.00 118.00   0.50    1.50    --   54.00  73.00 -48.29  168
 23  ω     33.00 118.00   0.50    1.50    --   54.00  74.00 -72.06  170
 24  ω     34.00 118.00   0.50    1.50    --   54.00  73.00 -96.40  168
 25  ω     33.00 118.00   0.50    1.50    --   54.00  74.00  97.72  170
 26  ω     34.00 118.00   0.50    1.50    --   54.00  73.00  -3.28  168
 27  ω     39.00 122.00   0.50    1.50    --   58.00  72.00 132.07  166
 28  ω     37.00 122.00   0.50    1.50    --   58.00  74.00  49.11  170
 29  ω     37.00 122.00   0.50    1.50    --   58.00  74.00  23.19  170
 30  ω     37.00 122.00   0.50    1.50    --   58.00  74.00 -27.85  170
 31  ω     40.00 121.00   0.50    1.50    --   58.00  69.00 118.11  162
 32  ω     41.00 126.00   0.50    1.50    --   62.00  74.00-153.67  170
 33  ω     54.00 129.00   0.50    1.50    --   66.00  58.00  10.25  150
 34  ω     48.00 129.00   0.50    1.50    --   66.00  70.00-121.87  162
 35  ω     52.00 133.00   0.50    1.50    --   70.00  69.00 -36.05  162
 36  ω     50.00  76.00   0.50    1.50    --   70.00  73.00  64.23   52
 37  ω     53.00  88.00   0.50    1.50    --   70.00  67.00 112.89   70
 38  ω     96.00 123.00   0.50    1.50    --   70.00  73.00 159.82   54
 39  ω     50.00  84.00   0.50    1.50    --   70.00  73.00 159.82   68
 40  ω     54.00  87.00   0.50    1.50    --   70.00  67.00 -85.19   66
 41  ω     63.00  90.00   0.50    1.50    --   74.00  57.00  24.77   54
 42  ω     94.00 119.00   0.50    1.50    --   74.00  72.00 118.30   50
 43  ω     55.00 106.00   0.50    1.50    --   74.00  72.00 136.59  102
 44  ω     57.00  90.00   0.50    1.50    --   74.00  72.00 118.30   66
 45  ω     71.00 123.00   0.50    7.00    --   82.00  56.00  51.18  104
 46  ω     62.00 102.00   0.50    7.00    --   82.00  73.00-175.90   80
 47  ω     69.00  94.00   0.50    7.00    --   82.00  61.00 -84.37   50
 48  ω    120.00 149.00   0.50    7.00    --   86.00  62.00  67.93   58
 49  ω     72.00 104.00   0.50    7.00    --   86.00  62.00  67.93   64
 50  ω     66.00 146.00   0.50    7.00    --   86.00  73.00-147.15  160
 51  ω     72.00 108.00   0.50    7.00    --  102.63-106.00 -49.61   72
 52  ω     99.00 158.00   0.50    7.00    --  102.63  45.00-180.00  118
 53  ω     34.00  68.00   0.50    7.00    --  102.63-106.00 -49.61   68
 54  ω    134.00 166.00   0.50    7.00    --  102.63  45.00  90.00   64
 55  ω     90.00 155.00   0.50    7.00    --  102.63  61.00   0.00  130
 56  ω     74.00 102.00   0.50    7.00    --  102.63 -30.00 150.00   56
 57  ω     36.00  62.00   0.50    7.00    --  102.63 -30.00 150.00   52
 58  ω    132.00 164.00   0.50    7.00    --  102.63  61.00 -90.00   64
 59  ω     92.00 137.00   0.50    7.00    --  102.63  61.00  90.00   90
 60  ω     98.00 131.00   0.50    7.00    --  102.63  45.00  90.00   66
 61  ω     91.00 147.00   0.50    7.00    --  102.63  61.00-120.00  112
 62  ω     93.00 119.00   0.50    7.00    --  102.63  61.00 -90.00   52
 63  ω    107.00 159.00   0.50    7.00    --  102.63 125.00-150.00  104
 64  ω     90.00 157.00   0.50    7.00    --  102.63  61.00 -60.00  134
 65  ω     92.00 152.00   0.50    7.00    --  102.63  61.00 -30.00  120
 66  ω     90.00 165.00   0.50    7.00    --  102.63  61.00 150.00  150
 67  ω     44.00  97.00   0.50    7.00    --  102.63-125.00  60.00  106
 68  ω     76.00 112.00   0.50    7.00    --  102.63-125.00  90.00   72
 69  ω     34.00 107.00   0.50    7.00    --  102.63 -94.00-180.00  146
 70  ω     49.00  75.00   0.50    7.00    --  102.63-125.00  90.00   52
 71  ω     81.00 106.00   0.50    7.00    --  102.63 -30.00 120.00   50
 72  ω     39.00 104.00   0.50    7.00    --  102.63 -45.00 -60.00  130
 73  ω     91.00 160.00   0.50    7.00    --  102.63  61.00 120.00  138
 74  ω     36.00  61.00   0.50    7.00    --  102.63 -94.00   0.00   50
 75  ω     49.00  97.00   0.50    7.00    --  102.63 -94.00-120.00   96
 76  ω    102.00 167.00   0.50    7.00    --  102.63  45.00  30.00  130
 77  ω    136.00 163.00   0.50    7.00    --  102.63  45.00-150.00   54
 78  ω     36.00  65.00   0.50    7.00    --  102.63 -30.00 120.00   58
 79  ω     71.00 106.00   0.50    7.00    --  102.63 -94.00   0.00   70
 80  ω    100.00 131.00   0.50    7.00    --  102.63  45.00-150.00   62
 81  ω     42.00 107.00   0.50    7.00    --  102.63 -45.00-150.00  130
 82  ω     85.00 115.00   0.50    7.00    --  102.63 -61.00  30.00   60
 83  ω     49.00  75.00   0.50    7.00    --  102.63 -61.00  30.00   52
 84  ω    101.00 141.00   0.50    7.00    --  102.63  45.00 -60.00   80
 85  ω     64.00  89.00   0.50    7.00    --  102.63-155.00  31.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0334278000
_diffrn_orient_matrix_UB_12      0.1076393000
_diffrn_orient_matrix_UB_13      -0.0597015000
_diffrn_orient_matrix_UB_21      -0.0004158000
_diffrn_orient_matrix_UB_22      -0.0911140000
_diffrn_orient_matrix_UB_23      -0.0725980000
_diffrn_orient_matrix_UB_31      -0.1916583000
_diffrn_orient_matrix_UB_32      0.0190163000
_diffrn_orient_matrix_UB_33      -0.0102319000
_diffrn_oxdiff_digest_frames     
;
0110996049e2581e81e76690d13068c74a000291d79
;
_diffrn_oxdiff_digest_hkl        
;
01bcd5ea6bdbddd7181dada14065c90f636b18
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2713
_reflns_number_total             2873
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1209 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.072
_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)+(0.0499P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00C,H00D)
;
_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
O001 O 0.8517(2) 0.19953(9) 0.64873(15) 0.0609(4) Uani 1 1 d . . . . .
O002 O 0.9978(3) 0.25047(12) 0.80483(18) 0.0776(5) Uani 1 1 d . . . . .
N003 N 0.8984(3) 0.41116(12) 0.76158(18) 0.0613(5) Uani 1 1 d . . . . .
O004 O 0.5167(3) 0.24099(12) 0.20843(18) 0.0781(6) Uani 1 1 d . . . . .
O005 O 0.8396(3) 0.41481(15) 0.86472(19) 0.0960(7) Uani 1 1 d . . . . .
O006 O 0.9997(3) 0.45960(13) 0.7195(2) 0.0866(6) Uani 1 1 d . . . . .
C007 C 0.7625(3) 0.21084(13) 0.5404(2) 0.0521(5) Uani 1 1 d . . . . .
C008 C 0.7527(3) 0.35879(11) 0.57903(18) 0.0455(4) Uani 1 1 d . . . . .
C009 C 0.9042(3) 0.26349(14) 0.7193(2) 0.0568(5) Uani 1 1 d . . . . .
C00A C 0.6875(3) 0.44224(11) 0.55101(19) 0.0470(4) Uani 1 1 d . . . . .
C00B C 0.6442(3) 0.14952(15) 0.3600(3) 0.0649(6) Uani 1 1 d . . . . .
H00B H 0.6212 0.1031 0.3128 0.078 Uiso 1 1 calc R . . . .
C00C C 0.7124(3) 0.28899(12) 0.50032(19) 0.0475(4) Uani 1 1 d . . . . .
C00D C 0.5957(3) 0.22659(14) 0.3176(2) 0.0584(5) Uani 1 1 d . . . . .
C00E C 0.8437(3) 0.34362(12) 0.68099(19) 0.0509(5) Uani 1 1 d . . . . .
C00F C 0.7260(3) 0.14164(14) 0.4716(3) 0.0630(6) Uani 1 1 d . . . . .
H00F H 0.7565 0.0900 0.5005 0.076 Uiso 1 1 calc R . . . .
C00G C 0.5708(3) 0.47706(14) 0.6307(2) 0.0591(5) Uani 1 1 d . . . . .
H00G H 0.5368 0.4488 0.7010 0.071 Uiso 1 1 calc R . . . .
C00H C 0.7404(3) 0.48535(14) 0.4481(2) 0.0571(5) Uani 1 1 d . . . . .
H00H H 0.8194 0.4624 0.3947 0.069 Uiso 1 1 calc R . . . .
C00I C 0.6275(3) 0.29573(13) 0.38834(19) 0.0524(5) Uani 1 1 d . . . . .
H00I H 0.5919 0.3469 0.3608 0.063 Uiso 1 1 calc R . . . .
C00J C 0.6753(4) 0.56296(15) 0.4244(3) 0.0676(6) Uani 1 1 d . . . . .
H00J H 0.7116 0.5922 0.3556 0.081 Uiso 1 1 calc R . . . .
C00K C 0.5573(4) 0.59664(15) 0.5026(3) 0.0748(7) Uani 1 1 d . . . . .
H00K H 0.5128 0.6483 0.4862 0.090 Uiso 1 1 calc R . . . .
C00L C 0.5053(4) 0.55356(16) 0.6056(3) 0.0749(7) Uani 1 1 d . . . . .
H00L H 0.4254 0.5763 0.6584 0.090 Uiso 1 1 calc R . . . .
C00M C 0.4771(6) 0.1734(2) 0.1310(3) 0.0981(10) Uani 1 1 d . . . . .
H00A H 0.4090 0.1918 0.0631 0.147 Uiso 1 1 calc GR . . . .
H00C H 0.4159 0.1330 0.1776 0.147 Uiso 1 1 calc GR . . . .
H00D H 0.5796 0.1496 0.1000 0.147 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
O001 C007 1.381(3) . ?
O001 C009 1.358(3) . ?
O002 C009 1.205(3) . ?
N003 O005 1.211(3) . ?
N003 O006 1.214(3) . ?
N003 C00E 1.470(3) . ?
O004 C00D 1.357(3) . ?
O004 C00M 1.420(3) . ?
C007 C00C 1.403(3) . ?
C007 C00F 1.382(3) . ?
C008 C00A 1.486(3) . ?
C008 C00C 1.457(3) . ?
C008 C00E 1.341(3) . ?
C009 C00E 1.451(3) . ?
C00A C00G 1.385(3) . ?
C00A C00H 1.382(3) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.391(4) . ?
C00B C00F 1.376(4) . ?
C00C C00I 1.390(3) . ?
C00D C00I 1.386(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00L 1.377(3) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.389(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00K 1.375(4) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.380(4) . ?
C00L H00L 0.9300 . ?
C00M H00A 0.9600 . ?
C00M H00C 0.9600 . ?
C00M H00D 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
C009 O001 C007 122.16(16) . . ?
O005 N003 O006 124.6(2) . . ?
O005 N003 C00E 118.1(2) . . ?
O006 N003 C00E 117.3(2) . . ?
C00D O004 C00M 118.8(2) . . ?
O001 C007 C00C 121.89(18) . . ?
O001 C007 C00F 117.1(2) . . ?
C00F C007 C00C 121.0(2) . . ?
C00C C008 C00A 121.28(18) . . ?
C00E C008 C00A 121.56(18) . . ?
C00E C008 C00C 117.08(17) . . ?
O001 C009 C00E 115.4(2) . . ?
O002 C009 O001 119.1(2) . . ?
O002 C009 C00E 125.5(2) . . ?
C00G C00A C008 118.65(19) . . ?
C00H C00A C008 121.64(19) . . ?
C00H C00A C00G 119.71(19) . . ?
C00D C00B H00B 119.9 . . ?
C00F C00B H00B 119.9 . . ?
C00F C00B C00D 120.3(2) . . ?
C007 C00C C008 117.78(18) . . ?
C00I C00C C007 118.57(18) . . ?
C00I C00C C008 123.65(18) . . ?
O004 C00D C00B 124.8(2) . . ?
O004 C00D C00I 115.1(2) . . ?
C00I C00D C00B 120.1(2) . . ?
C008 C00E N003 120.58(18) . . ?
C008 C00E C009 125.34(19) . . ?
C009 C00E N003 114.00(19) . . ?
C007 C00F H00F 120.1 . . ?
C00B C00F C007 119.7(2) . . ?
C00B C00F H00F 120.1 . . ?
C00A C00G H00G 120.0 . . ?
C00L C00G C00A 120.0(2) . . ?
C00L C00G H00G 120.0 . . ?
C00A C00H H00H 120.0 . . ?
C00A C00H C00J 119.9(2) . . ?
C00J C00H H00H 120.0 . . ?
C00C C00I H00I 119.8 . . ?
C00D C00I C00C 120.4(2) . . ?
C00D C00I H00I 119.8 . . ?
C00H C00J H00J 120.0 . . ?
C00K C00J C00H 120.1(2) . . ?
C00K C00J H00J 120.0 . . ?
C00J C00K H00K 120.1 . . ?
C00J C00K C00L 119.8(2) . . ?
C00L C00K H00K 120.1 . . ?
C00G C00L C00K 120.5(2) . . ?
C00G C00L H00L 119.8 . . ?
C00K C00L H00L 119.8 . . ?
O004 C00M H00A 109.5 . . ?
O004 C00M H00C 109.5 . . ?
O004 C00M H00D 109.5 . . ?
H00A C00M H00C 109.5 . . ?
H00A C00M H00D 109.5 . . ?
H00C C00M H00D 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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.577
