# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_170713_s1_wz
_database_code_depnum_ccdc_archive 'CCDC 1562681'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'(5-chloro-1-picolinoyl-1H-indol-3-yl)(phenyl)methyl acetate'
_chemical_formula_moiety         'C23 H17 Cl N2 O3'
_chemical_formula_sum            'C23 H17 Cl N2 O3'
_chemical_formula_weight         404.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3s1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.6917(10)
_cell_length_b                   7.5033(7)
_cell_length_c                   27.151(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.018(8)
_cell_angle_gamma                90
_cell_volume                     1971.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7700
_cell_measurement_theta_min      3.4260
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       solid
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            10239
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00   49.00   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000    0.0000 180

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   24.50   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   84.70   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5294  178.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   57.30   0.7000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5294 -104.0000  131.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0018451000
_diffrn_orient_matrix_UB_12      -0.0262993000
_diffrn_orient_matrix_UB_13      0.0250992000
_diffrn_orient_matrix_UB_21      0.0732109000
_diffrn_orient_matrix_UB_22      -0.0038048000
_diffrn_orient_matrix_UB_23      0.0003572000
_diffrn_orient_matrix_UB_31      0.0035612000
_diffrn_orient_matrix_UB_32      0.0907461000
_diffrn_orient_matrix_UB_33      0.0072944000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2655
_reflns_number_total             4036
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.027
_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)+(0.0610P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1509
_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 Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.90708(9) 0.79665(12) 0.51046(3) 0.0801(3) Uani 1 1 d . . . . .
O1 O 0.96831(19) 0.7362(3) 0.26040(7) 0.0628(5) Uani 1 1 d . . . . .
O2 O 0.36569(17) 0.9429(2) 0.31912(6) 0.0459(4) Uani 1 1 d . . . . .
O3 O 0.2832(3) 1.2037(3) 0.34279(10) 0.1048(10) Uani 1 1 d . . . . .
N1 N 0.7690(2) 0.7944(2) 0.29721(7) 0.0390(5) Uani 1 1 d . . . . .
N2 N 0.6485(2) 0.7344(3) 0.19621(8) 0.0554(6) Uani 1 1 d . . . . .
C1 C 0.8737(3) 0.7956(4) 0.44662(10) 0.0547(7) Uani 1 1 d . . . . .
C2 C 0.9798(3) 0.7546(4) 0.41610(11) 0.0651(8) Uani 1 1 d . . . . .
H2 H 1.0677 0.7305 0.4299 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9563(3) 0.7492(4) 0.36534(11) 0.0561(7) Uani 1 1 d . . . . .
H3 H 1.0267 0.7207 0.3447 0.067 Uiso 1 1 calc R . . . .
C4 C 0.8240(3) 0.7877(3) 0.34639(9) 0.0434(6) Uani 1 1 d . . . . .
C5 C 0.6305(2) 0.8465(3) 0.29861(9) 0.0387(6) Uani 1 1 d . . . . .
H5 H 0.5710 0.8627 0.2710 0.046 Uiso 1 1 calc R . . . .
C6 C 0.5953(2) 0.8701(3) 0.34567(8) 0.0371(5) Uani 1 1 d . . . . .
C7 C 0.7171(2) 0.8321(3) 0.37721(9) 0.0399(6) Uani 1 1 d . . . . .
C8 C 0.7420(3) 0.8344(3) 0.42839(9) 0.0464(6) Uani 1 1 d . . . . .
H8 H 0.6721 0.8612 0.4494 0.056 Uiso 1 1 calc R . . . .
C9 C 0.8457(3) 0.7707(3) 0.25574(9) 0.0433(6) Uani 1 1 d . . . . .
C10 C 0.7782(3) 0.7896(3) 0.20519(9) 0.0422(6) Uani 1 1 d . . . . .
C11 C 0.8586(3) 0.8557(3) 0.16876(9) 0.0500(7) Uani 1 1 d . . . . .
H11 H 0.9493 0.8907 0.1763 0.060 Uiso 1 1 calc R . . . .
C12 C 0.8031(3) 0.8691(4) 0.12123(11) 0.0598(8) Uani 1 1 d . . . . .
H12 H 0.8549 0.9154 0.0963 0.072 Uiso 1 1 calc R . . . .
C13 C 0.6713(3) 0.8137(4) 0.11139(11) 0.0627(8) Uani 1 1 d . . . . .
H13 H 0.6313 0.8206 0.0795 0.075 Uiso 1 1 calc R . . . .
C14 C 0.5976(3) 0.7468(4) 0.14931(11) 0.0679(9) Uani 1 1 d . . . . .
H14 H 0.5076 0.7082 0.1421 0.081 Uiso 1 1 calc R . . . .
C15 C 0.4593(2) 0.9347(3) 0.36258(8) 0.0401(6) Uani 1 1 d . . . . .
H15 H 0.4714 1.0551 0.3761 0.048 Uiso 1 1 calc R . . . .
C16 C 0.4020(2) 0.8154(3) 0.40170(8) 0.0388(6) Uani 1 1 d . . . . .
C17 C 0.3733(3) 0.6378(3) 0.39221(10) 0.0499(7) Uani 1 1 d . . . . .
H17 H 0.3822 0.5927 0.3606 0.060 Uiso 1 1 calc R . . . .
C18 C 0.3313(3) 0.5265(4) 0.42921(11) 0.0597(8) Uani 1 1 d . . . . .
H18 H 0.3135 0.4069 0.4226 0.072 Uiso 1 1 calc R . . . .
C19 C 0.3158(3) 0.5935(4) 0.47618(10) 0.0617(8) Uani 1 1 d . . . . .
H19 H 0.2889 0.5188 0.5013 0.074 Uiso 1 1 calc R . . . .
C20 C 0.3404(3) 0.7698(4) 0.48539(10) 0.0634(8) Uani 1 1 d . . . . .
H20 H 0.3291 0.8153 0.5168 0.076 Uiso 1 1 calc R . . . .
C21 C 0.3821(3) 0.8813(4) 0.44835(9) 0.0546(7) Uani 1 1 d . . . . .
H21 H 0.3969 1.0017 0.4549 0.065 Uiso 1 1 calc R . . . .
C22 C 0.2843(3) 1.0868(4) 0.31342(11) 0.0536(7) Uani 1 1 d . . . . .
C23 C 0.2000(3) 1.0790(4) 0.26631(11) 0.0694(9) Uani 1 1 d . . . . .
H23A H 0.2589 1.0924 0.2392 0.104 Uiso 1 1 calc GR . . . .
H23B H 0.1330 1.1733 0.2655 0.104 Uiso 1 1 calc GR . . . .
H23C H 0.1534 0.9662 0.2637 0.104 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
Cl1 C1 1.747(3) . ?
O1 C9 1.216(3) . ?
O2 C15 1.451(3) . ?
O2 C22 1.341(3) . ?
O3 C22 1.186(3) . ?
N1 C4 1.412(3) . ?
N1 C5 1.400(3) . ?
N1 C9 1.393(3) . ?
N2 C10 1.334(3) . ?
N2 C14 1.344(3) . ?
C1 C2 1.388(4) . ?
C1 C8 1.376(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 C7 1.406(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(3) . ?
C6 C7 1.449(3) . ?
C6 C15 1.499(3) . ?
C7 C8 1.398(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.496(3) . ?
C10 C11 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.356(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C15 C16 1.516(3) . ?
C16 C17 1.382(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.483(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O2 C15 117.79(19) . . ?
C5 N1 C4 107.40(19) . . ?
C9 N1 C4 124.6(2) . . ?
C9 N1 C5 127.6(2) . . ?
C10 N2 C14 116.5(2) . . ?
C2 C1 Cl1 119.3(2) . . ?
C8 C1 Cl1 118.4(2) . . ?
C8 C1 C2 122.3(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.6(3) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 N1 130.9(2) . . ?
C3 C4 C7 121.7(2) . . ?
C7 C4 N1 107.5(2) . . ?
N1 C5 H5 124.7 . . ?
C6 C5 N1 110.6(2) . . ?
C6 C5 H5 124.7 . . ?
C5 C6 C7 107.1(2) . . ?
C5 C6 C15 127.0(2) . . ?
C7 C6 C15 125.8(2) . . ?
C4 C7 C6 107.3(2) . . ?
C8 C7 C4 120.0(2) . . ?
C8 C7 C6 132.7(2) . . ?
C1 C8 C7 117.6(3) . . ?
C1 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
O1 C9 N1 120.2(2) . . ?
O1 C9 C10 119.6(2) . . ?
N1 C9 C10 120.2(2) . . ?
N2 C10 C9 120.1(2) . . ?
N2 C10 C11 122.8(2) . . ?
C11 C10 C9 117.0(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
N2 C14 C13 123.6(3) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
O2 C15 C6 106.65(18) . . ?
O2 C15 H15 108.8 . . ?
O2 C15 C16 111.02(18) . . ?
C6 C15 H15 108.8 . . ?
C6 C15 C16 112.57(18) . . ?
C16 C15 H15 108.8 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 C21 118.6(2) . . ?
C21 C16 C15 120.3(2) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.6(2) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
O2 C22 C23 111.2(2) . . ?
O3 C22 O2 123.0(3) . . ?
O3 C22 C23 125.8(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
Cl1 C1 C2 C3 178.7(2) . . . . ?
Cl1 C1 C8 C7 -179.71(18) . . . . ?
O1 C9 C10 N2 144.4(2) . . . . ?
O1 C9 C10 C11 -31.9(3) . . . . ?
O2 C15 C16 C17 59.4(3) . . . . ?
O2 C15 C16 C21 -122.9(2) . . . . ?
N1 C4 C7 C6 -1.2(2) . . . . ?
N1 C4 C7 C8 179.36(19) . . . . ?
N1 C5 C6 C7 0.2(2) . . . . ?
N1 C5 C6 C15 176.6(2) . . . . ?
N1 C9 C10 N2 -36.3(3) . . . . ?
N1 C9 C10 C11 147.4(2) . . . . ?
N2 C10 C11 C12 1.3(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C1 C8 C7 -0.2(4) . . . . ?
C2 C3 C4 N1 179.5(2) . . . . ?
C2 C3 C4 C7 0.5(4) . . . . ?
C3 C4 C7 C6 178.0(2) . . . . ?
C3 C4 C7 C8 -1.4(4) . . . . ?
C4 N1 C5 C6 -0.9(2) . . . . ?
C4 N1 C9 O1 2.4(3) . . . . ?
C4 N1 C9 C10 -176.91(19) . . . . ?
C4 C7 C8 C1 1.3(3) . . . . ?
C5 N1 C4 C3 -177.8(2) . . . . ?
C5 N1 C4 C7 1.3(2) . . . . ?
C5 N1 C9 O1 175.1(2) . . . . ?
C5 N1 C9 C10 -4.2(3) . . . . ?
C5 C6 C7 C4 0.6(3) . . . . ?
C5 C6 C7 C8 180.0(2) . . . . ?
C5 C6 C15 O2 8.0(3) . . . . ?
C5 C6 C15 C16 130.0(2) . . . . ?
C6 C7 C8 C1 -178.0(2) . . . . ?
C6 C15 C16 C17 -60.1(3) . . . . ?
C6 C15 C16 C21 117.6(3) . . . . ?
C7 C6 C15 O2 -176.28(19) . . . . ?
C7 C6 C15 C16 -54.3(3) . . . . ?
C8 C1 C2 C3 -0.7(4) . . . . ?
C9 N1 C4 C3 -3.8(4) . . . . ?
C9 N1 C4 C7 175.3(2) . . . . ?
C9 N1 C5 C6 -174.7(2) . . . . ?
C9 C10 C11 C12 177.5(2) . . . . ?
C10 N2 C14 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 N2 0.6(5) . . . . ?
C14 N2 C10 C9 -176.5(2) . . . . ?
C14 N2 C10 C11 -0.5(4) . . . . ?
C15 O2 C22 O3 -2.1(4) . . . . ?
C15 O2 C22 C23 177.4(2) . . . . ?
C15 C6 C7 C4 -175.8(2) . . . . ?
C15 C6 C7 C8 3.6(4) . . . . ?
C15 C16 C17 C18 174.9(2) . . . . ?
C15 C16 C21 C20 -174.8(2) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C16 C21 C20 2.9(4) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C18 C19 C20 C21 -0.7(5) . . . . ?
C19 C20 C21 C16 -1.2(5) . . . . ?
C21 C16 C17 C18 -2.8(4) . . . . ?
C22 O2 C15 C6 -136.3(2) . . . . ?
C22 O2 C15 C16 100.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_78
_database_code_depnum_ccdc_archive 'CCDC 1562684'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_audit_creation_date             2017-07-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
(3-benzoyl-5-isopropyl-3-methylindolin-1-yl)(pyridin-2-yl)methanone
_chemical_formula_moiety         'C25 H24 N2 O2'
_chemical_formula_sum            'C25 H24 N2 O2'
_chemical_formula_weight         384.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.3765(5)
_cell_length_b                   11.2190(6)
_cell_length_c                   12.1776(7)
_cell_angle_alpha                70.266(5)
_cell_angle_beta                 73.173(5)
_cell_angle_gamma                82.063(4)
_cell_volume                     1030.04(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3895
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.8170
_cell_measurement_theta_min      3.7070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.507
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3081
_reflns_number_total             4213
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.045
_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)+(0.0641P)²+0.4184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1648
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.2058(2) 0.49458(14) 0.42575(15) 0.0683(5) Uani 1 1 d . . . . .
O2 O 0.1371(2) 0.79227(17) 0.85303(15) 0.0728(5) Uani 1 1 d . . . . .
N1 N 0.2034(2) 0.60944(14) 0.54702(15) 0.0444(4) Uani 1 1 d . . . . .
N2 N 0.1350(3) 0.82604(17) 0.35333(17) 0.0642(5) Uani 1 1 d . . . . .
C1 C 0.2716(2) 0.51114(17) 0.63203(17) 0.0438(4) Uani 1 1 d . . . . .
H1A C 0.1197(2) 0.70865(19) 0.35510(18) 0.0473(5) Uani 1 1 d . . . . .
H1B C 0.3884(3) 0.80824(18) 0.70247(18) 0.0476(5) Uani 1 1 d . . . . .
H1C C 0.2464(2) 0.54116(18) 0.73711(18) 0.0464(5) Uani 1 1 d . . . . .
C2 C 0.2195(3) 0.75717(19) 0.76855(18) 0.0500(5) Uani 1 1 d . . . . .
H2 C 0.1786(3) 0.59649(18) 0.44573(19) 0.0476(5) Uani 1 1 d . . . . .
C3 C 0.5190(3) 0.7441(2) 0.6419(2) 0.0557(5) Uani 1 1 d . . . . .
H3A H 0.5033 0.6640 0.6409 0.067 Uiso 1 1 calc R . . . .
H3B C 0.1527(3) 0.71913(18) 0.59267(18) 0.0479(5) Uani 1 1 d . . . . .
H3C H 0.0446 0.7550 0.5804 0.058 Uiso 1 1 calc R . . . .
C4 H 0.2338 0.7843 0.5516 0.058 Uiso 1 1 calc R . . . .
C5 C 0.1442(3) 0.66604(18) 0.72889(18) 0.0474(5) Uani 1 1 d . . . . .
H5 C 0.3074(3) 0.4611(2) 0.8315(2) 0.0563(5) Uani 1 1 d . . . . .
C6 H 0.2881 0.4815 0.9024 0.068 Uiso 1 1 calc R . . . .
H6 C 0.3590(3) 0.39947(19) 0.6204(2) 0.0551(5) Uani 1 1 d . . . . .
C7 H 0.3753 0.3776 0.5506 0.066 Uiso 1 1 calc R . . . .
C8 C 0.3981(3) 0.3493(2) 0.8207(2) 0.0602(6) Uani 1 1 d . . . . .
C9 C 0.4206(3) 0.3223(2) 0.7150(2) 0.0602(6) Uani 1 1 d . . . . .
H9 H 0.4804 0.2481 0.7071 0.072 Uiso 1 1 calc R . . . .
C10 C 0.6716(3) 0.7978(2) 0.5832(2) 0.0637(6) Uani 1 1 d . . . . .
C11 H 0.7577 0.7540 0.5427 0.076 Uiso 1 1 calc R . . . .
H11A C 0.6973(3) 0.9158(2) 0.5843(2) 0.0663(6) Uani 1 1 d . . . . .
H11B H 0.8003 0.9519 0.5446 0.080 Uiso 1 1 calc R . . . .
H11C C 0.4183(3) 0.9270(2) 0.7031(2) 0.0634(6) Uani 1 1 d . . . . .
C12 H 0.3338 0.9712 0.7444 0.076 Uiso 1 1 calc R . . . .
H12A C 0.5702(3) 0.9797(2) 0.6440(3) 0.0722(7) Uani 1 1 d . . . . .
H12B H 0.5870 1.0598 0.6445 0.087 Uiso 1 1 calc R . . . .
C13 C 0.0262(3) 0.9067(3) 0.1802(2) 0.0730(7) Uani 1 1 d . . . . .
C14 H -0.0067 0.9766 0.1224 0.088 Uiso 1 1 calc R . . . .
C15 C -0.0357(3) 0.6406(2) 0.8041(2) 0.0685(7) Uani 1 1 d . . . . .
H15 H -0.0835 0.5877 0.7754 0.103 Uiso 1 1 calc GR . . . .
C16 H -0.0996 0.7195 0.7968 0.103 Uiso 1 1 calc GR . . . .
H16 H -0.0369 0.5986 0.8873 0.103 Uiso 1 1 calc GR . . . .
C17 C 0.0611(3) 0.6860(2) 0.2703(2) 0.0724(7) Uani 1 1 d . . . . .
H17 H 0.0531 0.6033 0.2727 0.087 Uiso 1 1 calc R . . . .
C18 C 0.0140(4) 0.7864(3) 0.1814(3) 0.0836(8) Uani 1 1 d . . . . .
H18 H -0.0255 0.7723 0.1231 0.100 Uiso 1 1 calc R . . . .
C19 C 0.0884(4) 0.9211(2) 0.2667(2) 0.0759(8) Uani 1 1 d . . . . .
C20 H 0.0989 1.0032 0.2649 0.091 Uiso 1 1 calc R . . . .
C21 C 0.4720(4) 0.2586(3) 0.9195(3) 0.0810(8) Uani 1 1 d . . . . .
H21 H 0.5704 0.2171 0.8783 0.097 Uiso 1 1 calc R . . . .
C22 C 0.3525(5) 0.1534(3) 0.9988(3) 0.1028(11) Uani 1 1 d . . . . .
H22 H 0.2470 0.1901 1.0325 0.154 Uiso 1 1 calc GR . . . .
C23 H 0.3985 0.0985 1.0629 0.154 Uiso 1 1 calc GR . . . .
H23 H 0.3368 0.1056 0.9509 0.154 Uiso 1 1 calc GR . . . .
C24 C 0.5339(6) 0.3219(4) 0.9864(4) 0.1196(13) Uani 1 1 d . . . . .
H24 H 0.6041 0.3889 0.9302 0.179 Uiso 1 1 calc GR . . . .
C25 H 0.5969 0.2615 1.0367 0.179 Uiso 1 1 calc GR . . . .
H25 H 0.4410 0.3565 1.0358 0.179 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
O1 H2 1.226(2) . ?
O2 C2 1.215(2) . ?
N1 C1 1.418(2) . ?
N1 H2 1.365(3) . ?
N1 H3B 1.478(2) . ?
N2 H1A 1.333(3) . ?
N2 C19 1.329(3) . ?
C1 H1C 1.382(3) . ?
C1 H6 1.390(3) . ?
H1A H2 1.500(3) . ?
H1A C17 1.371(3) . ?
H1B C2 1.494(3) . ?
H1B C3 1.391(3) . ?
H1B H11C 1.392(3) . ?
H1C C5 1.526(3) . ?
H1C H5 1.380(3) . ?
C2 C5 1.537(3) . ?
C3 H3A 0.9300 . ?
C3 C10 1.379(3) . ?
H3B H3C 0.9700 . ?
H3B C4 0.9700 . ?
H3B C5 1.545(3) . ?
C5 C15 1.528(3) . ?
H5 C6 0.9300 . ?
H5 C8 1.399(3) . ?
H6 C7 0.9300 . ?
H6 C9 1.375(3) . ?
C8 C9 1.376(3) . ?
C8 C21 1.515(3) . ?
C9 H9 0.9300 . ?
C10 C11 0.9300 . ?
C10 H11A 1.375(3) . ?
H11A H11B 0.9300 . ?
H11A H12A 1.367(4) . ?
H11C C12 0.9300 . ?
H11C H12A 1.370(4) . ?
H12A H12B 0.9300 . ?
C13 C14 0.9300 . ?
C13 C18 1.363(4) . ?
C13 C19 1.366(4) . ?
C15 H15 0.9600 . ?
C15 C16 0.9600 . ?
C15 H16 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.377(4) . ?
C18 H18 0.9300 . ?
C19 C20 0.9300 . ?
C21 H21 0.9800 . ?
C21 C22 1.524(4) . ?
C21 C24 1.474(4) . ?
C22 H22 0.9600 . ?
C22 C23 0.9600 . ?
C22 H23 0.9600 . ?
C24 H24 0.9600 . ?
C24 C25 0.9600 . ?
C24 H25 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
C1 N1 H3B 108.78(15) . . ?
H2 N1 C1 123.65(16) . . ?
H2 N1 H3B 127.36(16) . . ?
C19 N2 H1A 117.3(2) . . ?
H1C C1 N1 110.33(16) . . ?
H1C C1 H6 120.16(19) . . ?
H6 C1 N1 129.47(19) . . ?
N2 H1A H2 120.41(18) . . ?
N2 H1A C17 121.8(2) . . ?
C17 H1A H2 117.68(19) . . ?
C3 H1B C2 124.33(18) . . ?
C3 H1B H11C 117.7(2) . . ?
H11C H1B C2 118.00(19) . . ?
C1 H1C C5 110.15(17) . . ?
H5 H1C C1 120.65(19) . . ?
H5 H1C C5 129.18(19) . . ?
O2 C2 H1B 119.08(19) . . ?
O2 C2 C5 119.2(2) . . ?
H1B C2 C5 121.66(17) . . ?
O1 H2 N1 121.26(19) . . ?
O1 H2 H1A 118.62(19) . . ?
N1 H2 H1A 120.11(17) . . ?
H1B C3 H3A 119.6 . . ?
C10 C3 H1B 120.7(2) . . ?
C10 C3 H3A 119.6 . . ?
N1 H3B H3C 110.7 . . ?
N1 H3B C4 110.7 . . ?
N1 H3B C5 105.34(15) . . ?
H3C H3B C4 108.8 . . ?
C5 H3B H3C 110.7 . . ?
C5 H3B C4 110.7 . . ?
H1C C5 C2 112.59(17) . . ?
H1C C5 H3B 101.92(15) . . ?
H1C C5 C15 110.07(17) . . ?
C2 C5 H3B 111.07(16) . . ?
C15 C5 C2 110.20(17) . . ?
C15 C5 H3B 110.74(18) . . ?
H1C H5 C6 120.0 . . ?
H1C H5 C8 120.1(2) . . ?
C8 H5 C6 120.0 . . ?
C1 H6 C7 121.0 . . ?
C9 H6 C1 118.1(2) . . ?
C9 H6 C7 121.0 . . ?
H5 C8 C21 122.9(2) . . ?
C9 C8 H5 117.7(2) . . ?
C9 C8 C21 119.4(2) . . ?
H6 C9 C8 123.3(2) . . ?
H6 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C3 C10 C11 119.8 . . ?
H11A C10 C3 120.4(2) . . ?
H11A C10 C11 119.8 . . ?
C10 H11A H11B 120.3 . . ?
H12A H11A C10 119.5(2) . . ?
H12A H11A H11B 120.3 . . ?
H1B H11C C12 119.5 . . ?
H12A H11C H1B 121.1(2) . . ?
H12A H11C C12 119.5 . . ?
H11A H12A H11C 120.6(2) . . ?
H11A H12A H12B 119.7 . . ?
H11C H12A H12B 119.7 . . ?
C18 C13 C14 121.2 . . ?
C18 C13 C19 117.7(2) . . ?
C19 C13 C14 121.2 . . ?
C5 C15 H15 109.5 . . ?
C5 C15 C16 109.5 . . ?
C5 C15 H16 109.5 . . ?
H15 C15 C16 109.5 . . ?
H15 C15 H16 109.5 . . ?
C16 C15 H16 109.5 . . ?
H1A C17 H17 120.1 . . ?
H1A C17 C18 119.7(2) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 118.9(2) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
N2 C19 C13 124.6(2) . . ?
N2 C19 C20 117.7 . . ?
C13 C19 C20 117.7 . . ?
C8 C21 H21 105.8 . . ?
C8 C21 C22 110.2(2) . . ?
C22 C21 H21 105.8 . . ?
C24 C21 C8 113.8(2) . . ?
C24 C21 H21 105.8 . . ?
C24 C21 C22 114.7(3) . . ?
C21 C22 H22 109.5 . . ?
C21 C22 C23 109.5 . . ?
C21 C22 H23 109.5 . . ?
H22 C22 C23 109.5 . . ?
H22 C22 H23 109.5 . . ?
C23 C22 H23 109.5 . . ?
C21 C24 H24 109.5 . . ?
C21 C24 C25 109.5 . . ?
C21 C24 H25 109.5 . . ?
H24 C24 C25 109.5 . . ?
H24 C24 H25 109.5 . . ?
C25 C24 H25 109.5 . . ?

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
O2 C2 C5 H1C -120.1(2) . . . . ?
O2 C2 C5 H3B 126.3(2) . . . . ?
O2 C2 C5 C15 3.2(3) . . . . ?
N1 C1 H1C C5 3.5(2) . . . . ?
N1 C1 H1C H5 -177.82(17) . . . . ?
N1 C1 H6 C9 176.39(19) . . . . ?
N1 H3B C5 H1C 18.0(2) . . . . ?
N1 H3B C5 C2 138.19(16) . . . . ?
N1 H3B C5 C15 -99.02(19) . . . . ?
N2 H1A H2 O1 -160.2(2) . . . . ?
N2 H1A H2 N1 18.7(3) . . . . ?
N2 H1A C17 C18 -1.0(4) . . . . ?
C1 N1 H2 O1 4.2(3) . . . . ?
C1 N1 H2 H1A -174.70(16) . . . . ?
C1 N1 H3B C5 -17.2(2) . . . . ?
C1 H1C C5 C2 -132.67(18) . . . . ?
C1 H1C C5 H3B -13.6(2) . . . . ?
C1 H1C C5 C15 104.0(2) . . . . ?
C1 H1C H5 C8 1.1(3) . . . . ?
C1 H6 C9 C8 0.9(3) . . . . ?
H1A N2 C19 C13 0.1(4) . . . . ?
H1A C17 C18 C13 -0.3(4) . . . . ?
H1B C2 C5 H1C 62.6(2) . . . . ?
H1B C2 C5 H3B -50.9(2) . . . . ?
H1B C2 C5 C15 -174.04(19) . . . . ?
H1B C3 C10 H11A 0.3(4) . . . . ?
H1B H11C H12A H11A -1.0(4) . . . . ?
H1C C1 H6 C9 -1.0(3) . . . . ?
H1C H5 C8 C9 -1.2(3) . . . . ?
H1C H5 C8 C21 178.6(2) . . . . ?
C2 H1B C3 C10 -179.8(2) . . . . ?
C2 H1B H11C H12A -179.7(2) . . . . ?
H2 N1 C1 H1C -166.18(18) . . . . ?
H2 N1 C1 H6 16.2(3) . . . . ?
H2 N1 H3B C5 157.64(18) . . . . ?
H2 H1A C17 C18 -176.6(2) . . . . ?
C3 H1B C2 O2 152.4(2) . . . . ?
C3 H1B C2 C5 -30.3(3) . . . . ?
C3 H1B H11C H12A 1.3(3) . . . . ?
C3 C10 H11A H12A 0.0(4) . . . . ?
H3B N1 C1 H1C 8.9(2) . . . . ?
H3B N1 C1 H6 -168.7(2) . . . . ?
H3B N1 H2 O1 -169.9(2) . . . . ?
H3B N1 H2 H1A 11.2(3) . . . . ?
C5 H1C H5 C8 179.5(2) . . . . ?
H5 H1C C5 C2 48.8(3) . . . . ?
H5 H1C C5 H3B 167.9(2) . . . . ?
H5 H1C C5 C15 -74.5(3) . . . . ?
H5 C8 C9 H6 0.2(4) . . . . ?
H5 C8 C21 C22 94.6(3) . . . . ?
H5 C8 C21 C24 -35.7(4) . . . . ?
H6 C1 H1C C5 -178.63(18) . . . . ?
H6 C1 H1C H5 0.0(3) . . . . ?
C9 C8 C21 C22 -85.6(3) . . . . ?
C9 C8 C21 C24 144.1(3) . . . . ?
C10 H11A H12A H11C 0.3(4) . . . . ?
H11C H1B C2 O2 -26.4(3) . . . . ?
H11C H1B C2 C5 150.8(2) . . . . ?
H11C H1B C3 C10 -1.0(3) . . . . ?
C17 H1A H2 O1 15.4(3) . . . . ?
C17 H1A H2 N1 -165.6(2) . . . . ?
C18 C13 C19 N2 -1.3(5) . . . . ?
C19 N2 H1A H2 176.5(2) . . . . ?
C19 N2 H1A C17 1.1(4) . . . . ?
C19 C13 C18 C17 1.4(4) . . . . ?
C21 C8 C9 H6 -179.6(2) . . . . ?

_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.756
