# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_242
_database_code_depnum_ccdc_archive 'CCDC 1920021'
loop_
_audit_author_name
_audit_author_address
'Athira M'
;CSIR CLRI
India
;
_audit_update_record             
;
2019-05-31 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)-1-benzyl-3-(1-(9-hydroxy-9H-fluoren-9-yl)-2-oxo-2-phenylethylidene)indolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H25 N O3'
_chemical_formula_sum            'C36 H25 N O3'
_chemical_formula_weight         519.57

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.7530(5)
_cell_length_b                   19.4993(9)
_cell_length_c                   14.0108(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.635(2)
_cell_angle_gamma                90
_cell_volume                     2655.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    9358
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.64
_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61272
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5187
_reflns_number_gt                4075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.9637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0263(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5187
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.92928(17) 0.63907(9) 0.16043(12) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.99800(19) 0.59414(10) 0.10446(13) 0.0494(5) Uani 1 1 d . . . . .
H2 H 1.048791 0.557877 0.132166 0.059 Uiso 1 1 calc R U . . .
C3 C 0.9895(2) 0.60436(12) 0.00602(15) 0.0591(6) Uani 1 1 d . . . . .
H3 H 1.034946 0.574702 -0.032732 0.071 Uiso 1 1 calc R U . . .
C4 C 0.9139(2) 0.65827(13) -0.03460(15) 0.0634(6) Uani 1 1 d . . . . .
H4 H 0.908293 0.664076 -0.100680 0.076 Uiso 1 1 calc R U . . .
C5 C 0.8465(2) 0.70373(11) 0.02082(14) 0.0563(5) Uani 1 1 d . . . . .
H5 H 0.796299 0.740066 -0.007240 0.068 Uiso 1 1 calc R U . . .
C6 C 0.85502(18) 0.69411(9) 0.11950(12) 0.0424(4) Uani 1 1 d . . . . .
C7 C 0.79771(17) 0.73366(9) 0.19551(13) 0.0419(4) Uani 1 1 d . . . . .
C8 C 0.7170(2) 0.79257(10) 0.19205(16) 0.0573(5) Uani 1 1 d . . . . .
H8 H 0.688174 0.812688 0.133660 0.069 Uiso 1 1 calc R U . . .
C9 C 0.6805(2) 0.82056(11) 0.27654(18) 0.0646(6) Uani 1 1 d . . . . .
H9 H 0.626525 0.859925 0.274983 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7226(2) 0.79120(10) 0.36326(16) 0.0582(5) Uani 1 1 d . . . . .
H10 H 0.698184 0.811456 0.419524 0.070 Uiso 1 1 calc R U . . .
C11 C 0.80105(19) 0.73185(9) 0.36792(14) 0.0477(4) Uani 1 1 d . . . . .
H11 H 0.827856 0.711642 0.426604 0.057 Uiso 1 1 calc R U . . .
C12 C 0.83852(17) 0.70337(8) 0.28373(12) 0.0381(4) Uani 1 1 d . . . . .
C13 C 0.92001(16) 0.63745(8) 0.26834(12) 0.0362(4) Uani 1 1 d . . . . .
C14 C 0.83188(16) 0.57623(8) 0.29840(11) 0.0327(4) Uani 1 1 d . . . . .
C15 C 0.74481(17) 0.54479(8) 0.21518(11) 0.0354(4) Uani 1 1 d . . . . .
C16 C 0.61278(17) 0.57894(8) 0.18287(11) 0.0361(4) Uani 1 1 d . . . . .
C17 C 0.54446(18) 0.61998(10) 0.24415(13) 0.0461(4) Uani 1 1 d . . . . .
H17 H 0.582778 0.627706 0.306163 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4200(2) 0.64952(11) 0.21397(15) 0.0580(5) Uani 1 1 d . . . . .
H18 H 0.373479 0.676159 0.255966 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3651(2) 0.63949(13) 0.12201(17) 0.0700(6) Uani 1 1 d . . . . .
H19 H 0.281588 0.659766 0.101351 0.084 Uiso 1 1 calc R U . . .
C20 C 0.4331(3) 0.59949(14) 0.05997(17) 0.0791(7) Uani 1 1 d . . . . .
H20 H 0.395727 0.593170 -0.002610 0.095 Uiso 1 1 calc R U . . .
C21 C 0.5561(2) 0.56883(11) 0.09026(14) 0.0591(5) Uani 1 1 d . . . . .
H21 H 0.601032 0.541307 0.048458 0.071 Uiso 1 1 calc R U . . .
C22 C 0.82306(15) 0.55030(8) 0.38685(11) 0.0322(4) Uani 1 1 d . . . . .
C23 C 0.73206(16) 0.49531(8) 0.41689(11) 0.0328(4) Uani 1 1 d . . . . .
C24 C 0.63928(18) 0.45131(9) 0.36835(13) 0.0424(4) Uani 1 1 d . . . . .
H24 H 0.625164 0.453123 0.301954 0.051 Uiso 1 1 calc R U . . .
C25 C 0.56778(19) 0.40458(10) 0.41979(13) 0.0492(5) Uani 1 1 d . . . . .
H25 H 0.504688 0.375244 0.387560 0.059 Uiso 1 1 calc R U . . .
C26 C 0.5888(2) 0.40099(10) 0.51776(14) 0.0501(5) Uani 1 1 d . . . . .
H26 H 0.540303 0.368856 0.550734 0.060 Uiso 1 1 calc R U . . .
C27 C 0.68082(19) 0.44434(9) 0.56847(13) 0.0454(4) Uani 1 1 d . . . . .
H27 H 0.694720 0.442072 0.634847 0.055 Uiso 1 1 calc R U . . .
C28 C 0.75049(16) 0.49062(8) 0.51699(11) 0.0350(4) Uani 1 1 d . . . . .
C29 C 0.89925(16) 0.57500(8) 0.47878(11) 0.0347(4) Uani 1 1 d . . . . .
C30 C 0.89568(18) 0.54921(9) 0.65254(11) 0.0411(4) Uani 1 1 d . . . . .
H30A H 0.983657 0.572673 0.656997 0.049 Uiso 1 1 calc R U . . .
H30B H 0.909093 0.504858 0.683235 0.049 Uiso 1 1 calc R U . . .
C31 C 0.79517(17) 0.59027(9) 0.70558(11) 0.0376(4) Uani 1 1 d . . . . .
C32 C 0.77782(19) 0.65999(9) 0.68904(14) 0.0468(4) Uani 1 1 d . . . . .
H32 H 0.829132 0.681895 0.644924 0.056 Uiso 1 1 calc R U . . .
C33 C 0.6846(2) 0.69725(10) 0.73775(16) 0.0563(5) Uani 1 1 d . . . . .
H33 H 0.674013 0.744023 0.726472 0.068 Uiso 1 1 calc R U . . .
C34 C 0.6079(2) 0.66534(12) 0.80253(16) 0.0608(6) Uani 1 1 d . . . . .
H34 H 0.544772 0.690362 0.834681 0.073 Uiso 1 1 calc R U . . .
C35 C 0.6244(2) 0.59644(12) 0.81990(14) 0.0587(5) Uani 1 1 d . . . . .
H35 H 0.572805 0.574840 0.864134 0.070 Uiso 1 1 calc R U . . .
C36 C 0.7176(2) 0.55912(10) 0.77172(12) 0.0480(5) Uani 1 1 d . . . . .
H36 H 0.728237 0.512457 0.783917 0.058 Uiso 1 1 calc R U . . .
N1 N 0.85027(14) 0.53879(7) 0.55147(9) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.98804(12) 0.61970(6) 0.49046(9) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.78580(13) 0.49415(6) 0.17583(9) 0.0493(3) Uani 1 1 d . . . . .
O3 O 1.05586(12) 0.63629(6) 0.31274(10) 0.0444(3) Uani 1 1 d . . . . .
H3A H 1.047(3) 0.6370(12) 0.3802(19) 0.085(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.385(2) . ?
C1 C6 1.392(2) . ?
C1 C13 1.522(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.398(2) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.536(2) . ?
C13 O3 1.4177(19) . ?
C13 C14 1.549(2) . ?
C14 C22 1.348(2) . ?
C14 C15 1.515(2) . ?
C15 O2 1.2143(19) . ?
C15 C16 1.487(2) . ?
C16 C21 1.383(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.475(2) . ?
C22 C29 1.513(2) . ?
C23 C24 1.385(2) . ?
C23 C28 1.402(2) . ?
C24 C25 1.385(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.369(2) . ?
C27 H27 0.9300 . ?
C28 N1 1.410(2) . ?
C29 O1 1.2304(19) . ?
C29 N1 1.357(2) . ?
C30 N1 1.463(2) . ?
C30 C31 1.507(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C36 1.383(2) . ?
C31 C32 1.387(2) . ?
C32 C33 1.386(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.372(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(3) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
O3 H3A 0.96(3) . ?

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
C2 C1 C6 120.93(16) . . ?
C2 C1 C13 128.30(16) . . ?
C6 C1 C13 110.77(15) . . ?
C1 C2 C3 118.59(19) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.36(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 120.05(18) . . ?
C5 C6 C7 131.09(18) . . ?
C1 C6 C7 108.86(15) . . ?
C8 C7 C12 119.96(18) . . ?
C8 C7 C6 131.20(18) . . ?
C12 C7 C6 108.84(15) . . ?
C9 C8 C7 118.84(19) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.01(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 120.91(19) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.63(18) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C7 120.63(16) . . ?
C11 C12 C13 129.27(16) . . ?
C7 C12 C13 110.06(15) . . ?
O3 C13 C1 107.92(13) . . ?
O3 C13 C12 115.32(13) . . ?
C1 C13 C12 101.24(13) . . ?
O3 C13 C14 112.83(13) . . ?
C1 C13 C14 111.40(13) . . ?
C12 C13 C14 107.58(12) . . ?
C22 C14 C15 118.84(14) . . ?
C22 C14 C13 128.11(14) . . ?
C15 C14 C13 113.03(13) . . ?
O2 C15 C16 122.32(15) . . ?
O2 C15 C14 119.58(15) . . ?
C16 C15 C14 118.07(14) . . ?
C21 C16 C17 119.25(17) . . ?
C21 C16 C15 119.50(16) . . ?
C17 C16 C15 121.25(15) . . ?
C18 C17 C16 120.51(18) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.0(2) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C14 C22 C23 128.30(14) . . ?
C14 C22 C29 126.87(15) . . ?
C23 C22 C29 104.72(13) . . ?
C24 C23 C28 118.46(15) . . ?
C24 C23 C22 134.00(15) . . ?
C28 C23 C22 107.54(13) . . ?
C25 C24 C23 119.25(16) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 120.88(17) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 121.28(17) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 117.40(16) . . ?
C28 C27 H27 121.3 . . ?
C26 C27 H27 121.3 . . ?
C27 C28 C23 122.73(16) . . ?
C27 C28 N1 128.09(15) . . ?
C23 C28 N1 109.18(14) . . ?
O1 C29 N1 123.73(15) . . ?
O1 C29 C22 129.12(15) . . ?
N1 C29 C22 107.15(13) . . ?
N1 C30 C31 113.13(13) . . ?
N1 C30 H30A 109.0 . . ?
C31 C30 H30A 109.0 . . ?
N1 C30 H30B 109.0 . . ?
C31 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C36 C31 C32 118.44(16) . . ?
C36 C31 C30 120.65(16) . . ?
C32 C31 C30 120.91(16) . . ?
C33 C32 C31 120.50(18) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.19(19) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.95(19) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 120.1(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.85(19) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C29 N1 C28 111.38(13) . . ?
C29 N1 C30 123.82(14) . . ?
C28 N1 C30 124.80(14) . . ?
C13 O3 H3A 105.8(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.1(3) . . . . ?
C13 C1 C2 C3 178.21(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 178.86(18) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C13 C1 C6 C5 -177.97(15) . . . . ?
C2 C1 C6 C7 -178.17(15) . . . . ?
C13 C1 C6 C7 2.41(19) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C1 C6 C7 C8 179.88(18) . . . . ?
C5 C6 C7 C12 -178.74(18) . . . . ?
C1 C6 C7 C12 0.83(19) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -177.98(19) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 1.3(3) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C10 C11 C12 C13 -177.82(17) . . . . ?
C8 C7 C12 C11 -0.9(3) . . . . ?
C6 C7 C12 C11 178.30(16) . . . . ?
C8 C7 C12 C13 177.13(15) . . . . ?
C6 C7 C12 C13 -3.70(18) . . . . ?
C2 C1 C13 O3 54.8(2) . . . . ?
C6 C1 C13 O3 -125.81(15) . . . . ?
C2 C1 C13 C12 176.32(17) . . . . ?
C6 C1 C13 C12 -4.31(17) . . . . ?
C2 C1 C13 C14 -69.6(2) . . . . ?
C6 C1 C13 C14 109.81(15) . . . . ?
C11 C12 C13 O3 -61.2(2) . . . . ?
C7 C12 C13 O3 120.98(16) . . . . ?
C11 C12 C13 C1 -177.42(17) . . . . ?
C7 C12 C13 C1 4.80(17) . . . . ?
C11 C12 C13 C14 65.6(2) . . . . ?
C7 C12 C13 C14 -112.15(15) . . . . ?
O3 C13 C14 C22 44.0(2) . . . . ?
C1 C13 C14 C22 165.52(15) . . . . ?
C12 C13 C14 C22 -84.37(19) . . . . ?
O3 C13 C14 C15 -137.48(14) . . . . ?
C1 C13 C14 C15 -15.91(18) . . . . ?
C12 C13 C14 C15 94.20(15) . . . . ?
C22 C14 C15 O2 -84.13(19) . . . . ?
C13 C14 C15 O2 97.16(17) . . . . ?
C22 C14 C15 C16 97.64(17) . . . . ?
C13 C14 C15 C16 -81.07(17) . . . . ?
O2 C15 C16 C21 -21.6(2) . . . . ?
C14 C15 C16 C21 156.58(16) . . . . ?
O2 C15 C16 C17 157.52(17) . . . . ?
C14 C15 C16 C17 -24.3(2) . . . . ?
C21 C16 C17 C18 1.2(3) . . . . ?
C15 C16 C17 C18 -177.94(17) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 C16 -0.9(4) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C15 C16 C21 C20 179.2(2) . . . . ?
C15 C14 C22 C23 -3.3(2) . . . . ?
C13 C14 C22 C23 175.18(14) . . . . ?
C15 C14 C22 C29 -179.01(14) . . . . ?
C13 C14 C22 C29 -0.5(3) . . . . ?
C14 C22 C23 C24 5.3(3) . . . . ?
C29 C22 C23 C24 -178.22(17) . . . . ?
C14 C22 C23 C28 -174.45(15) . . . . ?
C29 C22 C23 C28 1.99(16) . . . . ?
C28 C23 C24 C25 0.2(2) . . . . ?
C22 C23 C24 C25 -179.55(17) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C26 C27 C28 N1 -178.73(16) . . . . ?
C24 C23 C28 C27 0.1(2) . . . . ?
C22 C23 C28 C27 179.96(15) . . . . ?
C24 C23 C28 N1 179.00(14) . . . . ?
C22 C23 C28 N1 -1.17(17) . . . . ?
C14 C22 C29 O1 -4.7(3) . . . . ?
C23 C22 C29 O1 178.84(16) . . . . ?
C14 C22 C29 N1 174.36(15) . . . . ?
C23 C22 C29 N1 -2.15(16) . . . . ?
N1 C30 C31 C36 108.26(18) . . . . ?
N1 C30 C31 C32 -71.5(2) . . . . ?
C36 C31 C32 C33 -0.1(3) . . . . ?
C30 C31 C32 C33 179.63(16) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C32 C33 C34 C35 0.6(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
C30 C31 C36 C35 -179.42(17) . . . . ?
O1 C29 N1 C28 -179.39(15) . . . . ?
C22 C29 N1 C28 1.53(17) . . . . ?
O1 C29 N1 C30 0.9(2) . . . . ?
C22 C29 N1 C30 -178.18(13) . . . . ?
C27 C28 N1 C29 178.53(16) . . . . ?
C23 C28 N1 C29 -0.26(18) . . . . ?
C27 C28 N1 C30 -1.8(3) . . . . ?
C23 C28 N1 C30 179.45(14) . . . . ?
C31 C30 N1 C29 101.89(18) . . . . ?
C31 C30 N1 C28 -77.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O1 0.96(3) 1.72(3) 2.6474(18) 161(2) . yes

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040

# start Validation Reply Form
_vrf_PLAT910_242                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         13 Note  
RESPONSE: These are outlier reflections which are cut by beamstop
in Bruker D8 VENTURE diffractometer. Hence these reflections are
omitted from refinement
;
# end Validation Reply Form


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_AM
_database_code_depnum_ccdc_archive 'CCDC 1936283'
loop_
_audit_author_name
_audit_author_address
'Athira Mohanakumaran'
;CSIR CLRI
India
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)-1-methyl-3-(2-oxo-2-phenyl-1-(9-(p-tolylamino)-9H-fluoren-9-yl)ethylidene)indolin-2-one
_chemical_name_common            AM3-3-F1
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H28 N2 O2'

_chemical_formula_sum            'C37 H28 N2 O2'
_chemical_formula_weight         532.61

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   11.867(3)
_cell_length_b                   12.900(3)
_cell_length_c                   18.148(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.427(17)
_cell_angle_gamma                90
_cell_volume                     2748.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9801
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      72.06

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.626
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6903
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'SADABS(BRUKER 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33648
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.187
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5186
_reflns_number_gt                3553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0961P)²+0.4671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0096(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5186
_refine_ls_number_parameters     377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1986
_refine_ls_wR_factor_gt          0.1688
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3860(2) 0.4442(3) 0.36389(19) 0.0809(9) Uani 1 1 d . . . . .
H1 H 0.342979 0.483024 0.392781 0.097 Uiso 1 1 calc R U . . .
C2 C 0.3321(3) 0.3738(3) 0.3131(2) 0.0888(10) Uani 1 1 d . . . . .
H2 H 0.253452 0.366282 0.309159 0.107 Uiso 1 1 calc R U . . .
C3 C 0.3900(3) 0.3146(3) 0.26854(19) 0.0775(9) Uani 1 1 d . . . . .
C4 C 0.5067(3) 0.3282(3) 0.2772(2) 0.0812(9) Uani 1 1 d . . . . .
H4 H 0.549218 0.289726 0.247839 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5626(2) 0.3979(2) 0.32874(18) 0.0765(8) Uani 1 1 d . . . . .
H5 H 0.641456 0.404005 0.333735 0.092 Uiso 1 1 calc R U . . .
C6 C 0.5025(2) 0.4581(2) 0.37250(15) 0.0601(7) Uani 1 1 d . . . . .
C7 C 0.6370(2) 0.60371(19) 0.40678(14) 0.0533(6) Uani 1 1 d . . . . .
C8 C 0.7524(2) 0.5527(2) 0.40130(15) 0.0562(6) Uani 1 1 d . . . . .
C9 C 0.8118(2) 0.4833(2) 0.45041(17) 0.0687(8) Uani 1 1 d . . . . .
H9 H 0.781911 0.459993 0.492032 0.082 Uiso 1 1 calc R U . . .
C10 C 0.9165(3) 0.4498(3) 0.4359(2) 0.0830(10) Uani 1 1 d . . . . .
H10 H 0.957573 0.402392 0.467907 0.100 Uiso 1 1 calc R U . . .
C11 C 0.9607(2) 0.4851(3) 0.3754(2) 0.0863(11) Uani 1 1 d . . . . .
H11 H 1.033025 0.463575 0.368097 0.104 Uiso 1 1 calc R U . . .
C12 C 0.9005(2) 0.5522(2) 0.32434(19) 0.0770(9) Uani 1 1 d . . . . .
H12 H 0.930309 0.574335 0.282420 0.092 Uiso 1 1 calc R U . . .
C13 C 0.7934(2) 0.5853(2) 0.33816(15) 0.0604(7) Uani 1 1 d . . . . .
C14 C 0.7056(2) 0.6471(2) 0.29274(14) 0.0595(7) Uani 1 1 d . . . . .
C15 C 0.7033(3) 0.6917(2) 0.22284(17) 0.0772(9) Uani 1 1 d . . . . .
H15 H 0.767343 0.689737 0.198890 0.093 Uiso 1 1 calc R U . . .
C16 C 0.6054(4) 0.7386(3) 0.18977(18) 0.0905(11) Uani 1 1 d . . . . .
H16 H 0.603425 0.768844 0.143075 0.109 Uiso 1 1 calc R U . . .
C17 C 0.5100(3) 0.7417(3) 0.22446(19) 0.0872(10) Uani 1 1 d . . . . .
H17 H 0.443557 0.771860 0.200235 0.105 Uiso 1 1 calc R U . . .
C18 C 0.5116(3) 0.7002(2) 0.29549(16) 0.0703(8) Uani 1 1 d . . . . .
H18 H 0.447786 0.704061 0.319575 0.084 Uiso 1 1 calc R U . . .
C19 C 0.6103(2) 0.6533(2) 0.32918(14) 0.0556(6) Uani 1 1 d . . . . .
C20 C 0.7664(2) 0.8604(2) 0.38827(16) 0.0631(7) Uani 1 1 d . . . . .
H20 H 0.689564 0.844746 0.375106 0.076 Uiso 1 1 calc R U . . .
C21 C 0.8146(3) 0.9377(2) 0.35119(19) 0.0793(9) Uani 1 1 d . . . . .
H21 H 0.770552 0.973859 0.313039 0.095 Uiso 1 1 calc R U . . .
C22 C 0.9274(3) 0.9614(3) 0.3703(2) 0.0933(11) Uani 1 1 d . . . . .
H22 H 0.960051 1.013690 0.345192 0.112 Uiso 1 1 calc R U . . .
C23 C 0.9924(3) 0.9079(3) 0.4269(3) 0.1055(13) Uani 1 1 d . . . . .
H23 H 1.068995 0.924480 0.439950 0.127 Uiso 1 1 calc R U . . .
C24 C 0.9455(3) 0.8302(3) 0.4645(2) 0.0839(10) Uani 1 1 d . . . . .
H24 H 0.990132 0.794389 0.502585 0.101 Uiso 1 1 calc R U . . .
C25 C 0.8309(2) 0.8054(2) 0.44502(15) 0.0612(7) Uani 1 1 d . . . . .
C26 C 0.7813(2) 0.7227(2) 0.48761(15) 0.0582(6) Uani 1 1 d . . . . .
C27 C 0.6574(2) 0.6926(2) 0.46480(14) 0.0569(6) Uani 1 1 d . . . . .
C28 C 0.5818(2) 0.7490(2) 0.49751(15) 0.0618(7) Uani 1 1 d . . . . .
C29 C 0.6069(3) 0.8362(2) 0.55074(16) 0.0683(8) Uani 1 1 d . . . . .
C30 C 0.7041(3) 0.8793(3) 0.59020(18) 0.0833(9) Uani 1 1 d . . . . .
H30 H 0.775047 0.852042 0.585115 0.100 Uiso 1 1 calc R U . . .
C31 C 0.6967(4) 0.9629(3) 0.6373(2) 0.1015(12) Uani 1 1 d . . . . .
H31 H 0.762848 0.991624 0.663149 0.122 Uiso 1 1 calc R U . . .
C32 C 0.5925(4) 1.0038(3) 0.6460(2) 0.1101(13) Uani 1 1 d . . . . .
H32 H 0.588597 1.060475 0.677240 0.132 Uiso 1 1 calc R U . . .
C33 C 0.4942(4) 0.9614(3) 0.6090(2) 0.1017(12) Uani 1 1 d . . . . .
H33 H 0.423654 0.988881 0.614978 0.122 Uiso 1 1 calc R U . . .
C34 C 0.5016(3) 0.8770(3) 0.56261(17) 0.0787(9) Uani 1 1 d . . . . .
C35 C 0.2924(3) 0.8409(4) 0.5199(2) 0.1115(14) Uani 1 1 d . . . . .
H35A H 0.249540 0.796688 0.483517 0.167 Uiso 1 1 calc R U . . .
H35B H 0.275813 0.912051 0.507210 0.167 Uiso 1 1 calc R U . . .
H35C H 0.271815 0.826528 0.568142 0.167 Uiso 1 1 calc R U . . .
C36 C 0.4535(3) 0.7426(3) 0.48258(17) 0.0690(8) Uani 1 1 d . . . . .
C37 C 0.3310(3) 0.2399(3) 0.2122(2) 0.1030(12) Uani 1 1 d . . . . .
H37A H 0.305241 0.180983 0.237326 0.155 Uiso 1 1 calc R U . . .
H37B H 0.383223 0.217543 0.179667 0.155 Uiso 1 1 calc R U . . .
H37C H 0.266947 0.273510 0.183432 0.155 Uiso 1 1 calc R U . . .
N1 N 0.5543(2) 0.52901(19) 0.42715(13) 0.0628(6) Uani 1 1 d . . . . .
N2 N 0.4133(2) 0.8218(2) 0.52135(15) 0.0812(8) Uani 1 1 d . . . . .
O1 O 0.83647(16) 0.68111(15) 0.54156(11) 0.0696(5) Uani 1 1 d . . . . .
O2 O 0.39148(18) 0.68226(19) 0.44337(13) 0.0831(7) Uani 1 1 d . . . . .
H1A H 0.497(3) 0.565(3) 0.4465(19) 0.109(13) Uiso 1 1 d . . . . .


_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
C1 C6 1.380(4) . ?
C1 C2 1.383(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(4) . ?
C3 C37 1.502(5) . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.421(4) . ?
C7 N1 1.461(3) . ?
C7 C8 1.536(3) . ?
C7 C19 1.537(3) . ?
C7 C27 1.552(4) . ?
C8 C13 1.375(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.467(4) . ?
C14 C15 1.390(4) . ?
C14 C19 1.393(3) . ?
C15 C16 1.367(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C20 C21 1.374(4) . ?
C20 C25 1.385(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.367(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.489(4) . ?
C26 O1 1.220(3) . ?
C26 C27 1.519(4) . ?
C27 C28 1.358(4) . ?
C28 C29 1.484(4) . ?
C28 C36 1.509(4) . ?
C29 C30 1.382(4) . ?
C29 C34 1.402(4) . ?
C30 C31 1.387(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.375(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.371(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(5) . ?
C33 H33 0.9300 . ?
C34 N2 1.391(4) . ?
C35 N2 1.453(4) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 O2 1.225(4) . ?
C36 N2 1.365(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
N1 H1A 0.94(3) . ?

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
C6 C1 C2 121.3(3) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 122.4(3) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 116.3(3) . . ?
C2 C3 C37 122.4(3) . . ?
C4 C3 C37 121.2(3) . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 117.1(3) . . ?
C1 C6 N1 119.1(3) . . ?
C5 C6 N1 123.8(2) . . ?
N1 C7 C8 111.8(2) . . ?
N1 C7 C19 116.8(2) . . ?
C8 C7 C19 100.6(2) . . ?
N1 C7 C27 111.1(2) . . ?
C8 C7 C27 107.98(19) . . ?
C19 C7 C27 107.7(2) . . ?
C13 C8 C9 121.8(3) . . ?
C13 C8 C7 110.5(2) . . ?
C9 C8 C7 127.7(3) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.7(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 117.6(3) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C8 C13 C12 119.9(3) . . ?
C8 C13 C14 109.0(2) . . ?
C12 C13 C14 130.9(3) . . ?
C15 C14 C19 120.1(3) . . ?
C15 C14 C13 131.0(3) . . ?
C19 C14 C13 108.9(2) . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.3(3) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 C7 129.5(2) . . ?
C14 C19 C7 109.8(2) . . ?
C21 C20 C25 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C25 C20 H20 119.6 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C20 C25 C24 119.0(3) . . ?
C20 C25 C26 122.4(2) . . ?
C24 C25 C26 118.6(3) . . ?
O1 C26 C25 121.7(3) . . ?
O1 C26 C27 119.4(3) . . ?
C25 C26 C27 118.9(2) . . ?
C28 C27 C26 114.8(2) . . ?
C28 C27 C7 130.2(2) . . ?
C26 C27 C7 115.0(2) . . ?
C27 C28 C29 127.5(3) . . ?
C27 C28 C36 127.3(3) . . ?
C29 C28 C36 105.1(2) . . ?
C30 C29 C34 117.7(3) . . ?
C30 C29 C28 135.7(3) . . ?
C34 C29 C28 106.6(3) . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 120.5(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C33 C32 C31 120.4(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 119.1(4) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C33 C34 N2 128.3(3) . . ?
C33 C34 C29 121.7(4) . . ?
N2 C34 C29 110.0(3) . . ?
N2 C35 H35A 109.5 . . ?
N2 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N2 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O2 C36 N2 123.3(3) . . ?
O2 C36 C28 130.1(3) . . ?
N2 C36 C28 106.6(3) . . ?
C3 C37 H37A 109.5 . . ?
C3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C6 N1 C7 119.1(2) . . ?
C6 N1 H1A 109(2) . . ?
C7 N1 H1A 109(2) . . ?
C36 N2 C34 111.6(3) . . ?
C36 N2 C35 122.4(3) . . ?
C34 N2 C35 125.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C37 -178.5(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C37 C3 C4 C5 179.4(3) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C1 C6 N1 -178.0(3) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 N1 178.6(3) . . . . ?
N1 C7 C8 C13 135.0(2) . . . . ?
C19 C7 C8 C13 10.3(3) . . . . ?
C27 C7 C8 C13 -102.5(2) . . . . ?
N1 C7 C8 C9 -44.9(4) . . . . ?
C19 C7 C8 C9 -169.7(3) . . . . ?
C27 C7 C8 C9 77.6(3) . . . . ?
C13 C8 C9 C10 2.3(4) . . . . ?
C7 C8 C9 C10 -177.8(3) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 -2.9(5) . . . . ?
C10 C11 C12 C13 1.8(4) . . . . ?
C9 C8 C13 C12 -3.3(4) . . . . ?
C7 C8 C13 C12 176.7(2) . . . . ?
C9 C8 C13 C14 172.6(2) . . . . ?
C7 C8 C13 C14 -7.3(3) . . . . ?
C11 C12 C13 C8 1.2(4) . . . . ?
C11 C12 C13 C14 -173.7(3) . . . . ?
C8 C13 C14 C15 -175.9(3) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C8 C13 C14 C19 0.7(3) . . . . ?
C12 C13 C14 C19 176.0(3) . . . . ?
C19 C14 C15 C16 -2.0(4) . . . . ?
C13 C14 C15 C16 174.3(3) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 2.2(6) . . . . ?
C16 C17 C18 C19 -1.9(5) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C17 C18 C19 C7 178.6(3) . . . . ?
C15 C14 C19 C18 2.3(4) . . . . ?
C13 C14 C19 C18 -174.7(2) . . . . ?
C15 C14 C19 C7 -176.8(2) . . . . ?
C13 C14 C19 C7 6.2(3) . . . . ?
N1 C7 C19 C18 49.9(4) . . . . ?
C8 C7 C19 C18 171.2(3) . . . . ?
C27 C7 C19 C18 -75.9(3) . . . . ?
N1 C7 C19 C14 -131.0(2) . . . . ?
C8 C7 C19 C14 -9.8(3) . . . . ?
C27 C7 C19 C14 103.2(2) . . . . ?
C25 C20 C21 C22 -0.3(5) . . . . ?
C20 C21 C22 C23 -0.1(5) . . . . ?
C21 C22 C23 C24 0.3(6) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C21 C20 C25 C26 178.6(3) . . . . ?
C23 C24 C25 C20 -0.3(5) . . . . ?
C23 C24 C25 C26 -178.6(3) . . . . ?
C20 C25 C26 O1 -173.6(2) . . . . ?
C24 C25 C26 O1 4.6(4) . . . . ?
C20 C25 C26 C27 4.1(4) . . . . ?
C24 C25 C26 C27 -177.8(3) . . . . ?
O1 C26 C27 C28 89.3(3) . . . . ?
C25 C26 C27 C28 -88.4(3) . . . . ?
O1 C26 C27 C7 -91.8(3) . . . . ?
C25 C26 C27 C7 90.5(3) . . . . ?
N1 C7 C27 C28 -45.4(3) . . . . ?
C8 C7 C27 C28 -168.4(3) . . . . ?
C19 C7 C27 C28 83.7(3) . . . . ?
N1 C7 C27 C26 135.9(2) . . . . ?
C8 C7 C27 C26 12.9(3) . . . . ?
C19 C7 C27 C26 -95.0(2) . . . . ?
C26 C27 C28 C29 1.3(4) . . . . ?
C7 C27 C28 C29 -177.4(2) . . . . ?
C26 C27 C28 C36 175.6(2) . . . . ?
C7 C27 C28 C36 -3.1(5) . . . . ?
C27 C28 C29 C30 -9.5(5) . . . . ?
C36 C28 C29 C30 175.2(3) . . . . ?
C27 C28 C29 C34 173.6(3) . . . . ?
C36 C28 C29 C34 -1.7(3) . . . . ?
C34 C29 C30 C31 -2.7(5) . . . . ?
C28 C29 C30 C31 -179.4(3) . . . . ?
C29 C30 C31 C32 0.6(6) . . . . ?
C30 C31 C32 C33 0.9(7) . . . . ?
C31 C32 C33 C34 -0.1(6) . . . . ?
C32 C33 C34 N2 178.8(4) . . . . ?
C32 C33 C34 C29 -2.1(6) . . . . ?
C30 C29 C34 C33 3.5(5) . . . . ?
C28 C29 C34 C33 -178.9(3) . . . . ?
C30 C29 C34 N2 -177.2(3) . . . . ?
C28 C29 C34 N2 0.3(3) . . . . ?
C27 C28 C36 O2 5.9(5) . . . . ?
C29 C28 C36 O2 -178.7(3) . . . . ?
C27 C28 C36 N2 -172.8(3) . . . . ?
C29 C28 C36 N2 2.5(3) . . . . ?
C1 C6 N1 C7 -132.8(3) . . . . ?
C5 C6 N1 C7 49.9(4) . . . . ?
C8 C7 N1 C6 -75.5(3) . . . . ?
C19 C7 N1 C6 39.7(3) . . . . ?
C27 C7 N1 C6 163.8(2) . . . . ?
O2 C36 N2 C34 178.7(3) . . . . ?
C28 C36 N2 C34 -2.4(3) . . . . ?
O2 C36 N2 C35 0.6(5) . . . . ?
C28 C36 N2 C35 179.5(3) . . . . ?
C33 C34 N2 C36 -179.4(3) . . . . ?
C29 C34 N2 C36 1.4(4) . . . . ?
C33 C34 N2 C35 -1.4(6) . . . . ?
C29 C34 N2 C35 179.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.94(3) 1.96(4) 2.810(3) 151(3) . yes

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
