# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cmrv-ad-662_mo
_database_code_depnum_ccdc_archive 'CCDC 1981050'
loop_
_audit_author_name
_audit_author_address
'Arnab Dey'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-05
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N3 O'
_chemical_formula_sum            'C24 H21 N3 O'
_chemical_formula_weight         367.44
_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                   9.3029(5)
_cell_length_b                   9.8555(6)
_cell_length_c                   11.3680(6)
_cell_angle_alpha                100.465(5)
_cell_angle_beta                 110.413(5)
_cell_angle_gamma                103.140(5)
_cell_volume                     911.54(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4238
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7760
_cell_measurement_theta_min      2.4460
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  258
  2  ω   -110.00  16.00   0.50    8.00    --  -20.00   0.00 -36.00  252
  3  ω    -78.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  194
  4  ω    -35.00   2.00   0.50    8.00    --  -20.00 -72.00-180.00   74
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0055672000
_diffrn_orient_matrix_UB_12      0.0247648000
_diffrn_orient_matrix_UB_13      0.0603340000
_diffrn_orient_matrix_UB_21      0.0854301000
_diffrn_orient_matrix_UB_22      0.0230066000
_diffrn_orient_matrix_UB_23      0.0327610000
_diffrn_orient_matrix_UB_31      0.0036654000
_diffrn_orient_matrix_UB_32      0.0692818000
_diffrn_orient_matrix_UB_33      -0.0103464000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2525
_reflns_number_total             3206
_reflns_odcompleteness_completeness 88.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.05
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.145
_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)+(0.0965P)²+0.1235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1814
_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), C24(H24), C16(H16), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C4(H4), C1(H1), C22(H22), C11(H11), C21(H21), C3(H3),
 C19(H19), C20(H20), C2(H2)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_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
O1 O 0.09190(19) 0.61164(17) 0.35402(15) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.4978(2) 0.67831(19) 0.73673(17) 0.0234(5) Uani 1 1 d . . . . .
N2 N 0.5170(2) 0.76773(19) 0.83739(17) 0.0241(5) Uani 1 1 d . . . . .
N1 N 0.7895(3) 0.7503(2) 0.92748(19) 0.0318(5) Uani 1 1 d . . . . .
C13 C 0.2091(3) 0.2529(2) 0.4098(2) 0.0257(5) Uani 1 1 d . . . . .
H13 H 0.1949 0.2145 0.3222 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3059(3) 0.5158(2) 0.4048(2) 0.0209(5) Uani 1 1 d . . . . .
H15 H 0.3983 0.5072 0.3815 0.025 Uiso 1 1 calc R . . . .
C14 C 0.2589(3) 0.4012(2) 0.4662(2) 0.0207(5) Uani 1 1 d . . . . .
C6 C 0.3298(3) 0.6253(2) 0.6321(2) 0.0220(5) Uani 1 1 d . . . . .
C12 C 0.1803(3) 0.1613(2) 0.4840(2) 0.0295(6) Uani 1 1 d . . . . .
H12 H 0.1432 0.0590 0.4462 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7127(3) 0.9351(2) 1.0374(2) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.6319 0.9784 1.0397 0.029 Uiso 1 1 calc R . . . .
C9 C 0.2563(3) 0.3682(2) 0.6720(2) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.6811(3) 0.8183(2) 0.9364(2) 0.0218(5) Uani 1 1 d . . . . .
C8 C 0.2789(3) 0.4592(2) 0.5944(2) 0.0210(5) Uani 1 1 d . . . . .
C7 C 0.2098(3) 0.6869(2) 0.6691(2) 0.0280(6) Uani 1 1 d . . . . .
H7A H 0.1991 0.6563 0.7438 0.042 Uiso 1 1 calc GR . . . .
H7B H 0.1044 0.6505 0.5944 0.042 Uiso 1 1 calc GR . . . .
H7C H 0.2491 0.7933 0.6928 0.042 Uiso 1 1 calc GR . . . .
C24 C 0.1660(3) 0.5294(2) 0.2880(2) 0.0257(5) Uani 1 1 d . . . . .
H24 H 0.0911 0.4353 0.2216 0.031 Uiso 1 1 calc R . . . .
C1 C 0.9381(3) 0.8039(3) 1.0265(2) 0.0310(6) Uani 1 1 d . . . . .
H1 H 1.0169 0.7582 1.0240 0.037 Uiso 1 1 calc R . . . .
C23 C 0.2447(3) 0.6400(2) 0.2344(2) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.3528(3) 0.6634(2) 0.5099(2) 0.0221(5) Uani 1 1 d . . . . .
H16 H 0.4674 0.7220 0.5351 0.026 Uiso 1 1 calc R . . . .
C22 C 0.2844(3) 0.6312(3) 0.1277(2) 0.0307(6) Uani 1 1 d . . . . .
H22 H 0.2542 0.5406 0.0647 0.037 Uiso 1 1 calc R . . . .
C11 C 0.2055(3) 0.2185(2) 0.6131(2) 0.0297(6) Uani 1 1 d . . . . .
H11 H 0.1875 0.1539 0.6629 0.036 Uiso 1 1 calc R . . . .
C21 C 0.3701(3) 0.7592(3) 0.1155(2) 0.0345(6) Uani 1 1 d . . . . .
H21 H 0.3958 0.7564 0.0414 0.041 Uiso 1 1 calc R . . . .
C10 C 0.2853(3) 0.4222(3) 0.8136(2) 0.0315(6) Uani 1 1 d . . . . .
H10A H 0.3841 0.5059 0.8584 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.2974 0.3445 0.8555 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.1934 0.4515 0.8190 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.2919(3) 0.7729(2) 0.3283(2) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.8654(3) 0.9877(3) 1.1356(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.8922 1.0697 1.2070 0.040 Uiso 1 1 calc R . . . .
C19 C 0.3805(3) 0.8988(3) 0.3172(2) 0.0326(6) Uani 1 1 d . . . . .
H19 H 0.4147 0.9890 0.3820 0.039 Uiso 1 1 calc R . . . .
C17 C 0.2353(3) 0.7354(2) 0.4315(2) 0.0263(5) Uani 1 1 d . . . . .
H17 H 0.2185 0.8171 0.4859 0.032 Uiso 1 1 calc R . . . .
C20 C 0.4185(3) 0.8905(3) 0.2090(2) 0.0353(6) Uani 1 1 d . . . . .
H20 H 0.4786 0.9762 0.1991 0.042 Uiso 1 1 calc R . . . .
C2 C 0.9794(3) 0.9225(3) 1.1311(2) 0.0318(6) Uani 1 1 d . . . . .
H2 H 1.0853 0.9585 1.1989 0.038 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
O1 C24 1.446(3) . ?
O1 C17 1.447(3) . ?
N3 N2 1.240(2) . ?
N3 C6 1.496(3) . ?
N2 C5 1.448(3) . ?
N1 C5 1.353(3) . ?
N1 C1 1.350(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C13 C12 1.385(3) . ?
C15 H15 1.0000 . ?
C15 C14 1.494(3) . ?
C15 C24 1.553(3) . ?
C15 C16 1.565(3) . ?
C14 C8 1.395(3) . ?
C6 C8 1.529(3) . ?
C6 C7 1.527(3) . ?
C6 C16 1.573(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(3) . ?
C4 C3 1.372(3) . ?
C9 C8 1.400(3) . ?
C9 C11 1.397(3) . ?
C9 C10 1.506(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C24 H24 1.0000 . ?
C24 C23 1.511(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(3) . ?
C23 C22 1.380(3) . ?
C23 C18 1.397(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.548(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.389(3) . ?
C11 H11 0.9500 . ?
C21 H21 0.9500 . ?
C21 C20 1.382(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C18 C19 1.378(3) . ?
C18 C17 1.514(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.370(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C17 H17 1.0000 . ?
C20 H20 0.9500 . ?
C2 H2 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O1 C17 96.64(16) . . ?
N2 N3 C6 114.46(18) . . ?
N3 N2 C5 113.29(18) . . ?
C1 N1 C5 116.5(2) . . ?
C14 C13 H13 120.7 . . ?
C14 C13 C12 118.5(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C15 H15 111.4 . . ?
C14 C15 C24 115.66(18) . . ?
C14 C15 C16 105.00(16) . . ?
C24 C15 H15 111.4 . . ?
C24 C15 C16 101.32(17) . . ?
C16 C15 H15 111.4 . . ?
C13 C14 C15 125.98(19) . . ?
C13 C14 C8 121.42(19) . . ?
C8 C14 C15 112.51(18) . . ?
N3 C6 C8 106.31(17) . . ?
N3 C6 C7 114.53(17) . . ?
N3 C6 C16 103.78(16) . . ?
C8 C6 C16 103.94(16) . . ?
C7 C6 C8 113.20(18) . . ?
C7 C6 C16 114.01(18) . . ?
C13 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C5 C4 H4 121.3 . . ?
C5 C4 C3 117.5(2) . . ?
C3 C4 H4 121.3 . . ?
C8 C9 C10 124.0(2) . . ?
C11 C9 C8 117.0(2) . . ?
C11 C9 C10 119.0(2) . . ?
N1 C5 N2 121.16(19) . . ?
N1 C5 C4 124.4(2) . . ?
C4 C5 N2 114.4(2) . . ?
C14 C8 C6 111.25(18) . . ?
C14 C8 C9 120.6(2) . . ?
C9 C8 C6 128.12(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C24 C15 102.05(16) . . ?
O1 C24 H24 115.2 . . ?
O1 C24 C23 101.59(17) . . ?
C15 C24 H24 115.2 . . ?
C23 C24 C15 105.87(18) . . ?
C23 C24 H24 115.2 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(2) . . ?
C2 C1 H1 118.8 . . ?
C22 C23 C24 134.3(2) . . ?
C22 C23 C18 121.0(2) . . ?
C18 C23 C24 104.47(19) . . ?
C15 C16 C6 107.07(17) . . ?
C15 C16 H16 110.5 . . ?
C6 C16 H16 110.5 . . ?
C17 C16 C15 100.79(17) . . ?
C17 C16 C6 117.00(18) . . ?
C17 C16 H16 110.5 . . ?
C23 C22 H22 121.1 . . ?
C23 C22 C21 117.8(2) . . ?
C21 C22 H22 121.1 . . ?
C12 C11 C9 122.0(2) . . ?
C12 C11 H11 119.0 . . ?
C9 C11 H11 119.0 . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C23 C18 C17 104.75(19) . . ?
C19 C18 C23 120.8(2) . . ?
C19 C18 C17 134.3(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.2(2) . . ?
C20 C19 H19 120.9 . . ?
O1 C17 C16 101.74(17) . . ?
O1 C17 C18 101.76(17) . . ?
O1 C17 H17 115.0 . . ?
C16 C17 H17 115.0 . . ?
C18 C17 C16 106.56(18) . . ?
C18 C17 H17 115.0 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.630
_oxdiff_exptl_absorpt_empirical_full_min 0.817
####################################################################### 
# 
# 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_cmrv-ad-668-a_mo
_database_code_depnum_ccdc_archive 'CCDC 1981052'
loop_
_audit_author_name
_audit_author_address
'Arnab Dey'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-09-25
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Cl2 N3 O'
_chemical_formula_sum            'C23 H17 Cl2 N3 O'
_chemical_formula_weight         422.29
_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'
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/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                   9.5063(7)
_cell_length_b                   12.2058(9)
_cell_length_c                   17.4137(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.384(7)
_cell_angle_gamma                90
_cell_volume                     1973.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.4600
_cell_measurement_theta_min      2.3930
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6563
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  67.00   0.50    8.00    --  -20.00   0.00 -36.00  354
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0058796000
_diffrn_orient_matrix_UB_12      -0.0221498000
_diffrn_orient_matrix_UB_13      0.0368375000
_diffrn_orient_matrix_UB_21      0.0714224000
_diffrn_orient_matrix_UB_22      -0.0202048000
_diffrn_orient_matrix_UB_23      0.0056708000
_diffrn_orient_matrix_UB_31      0.0264014000
_diffrn_orient_matrix_UB_32      0.0497791000
_diffrn_orient_matrix_UB_33      0.0187298000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2426
_reflns_number_total             3448
_reflns_odcompleteness_completeness 85.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.05
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0758
_refine_ls_restrained_S_all      1.100
_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)+(0.1471P)²+1.3073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2059
_refine_ls_wR_factor_ref         0.2686
_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:
 C9(H9), C8(H8), C10(H10), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C5(H5), C2(H2), C22(H22), C4(H4), C21(H21), C3(H3),
 C20(H20), C23(H23)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Cl1 Cl 0.13593(13) 0.52908(12) 0.23213(8) 0.0585(5) Uani 1 1 d . . . . .
Cl2 Cl 0.64914(16) 0.33888(12) 0.24998(8) 0.0660(5) Uani 1 1 d . . . . .
O1 O 0.7246(3) 0.7500(2) 0.42496(18) 0.0409(8) Uani 1 1 d . . . . .
C11 C 0.5083(4) 0.5633(3) 0.3853(2) 0.0312(9) Uani 1 1 d . . . . .
C9 C 0.5805(4) 0.6138(3) 0.4621(2) 0.0302(9) Uani 1 1 d . . . . .
H9 H 0.5328 0.5912 0.5056 0.036 Uiso 1 1 calc R . . . .
C16 C 0.6013(5) 0.4943(3) 0.3558(2) 0.0321(10) Uani 1 1 d . . . . .
C12 C 0.3647(5) 0.5761(3) 0.3473(2) 0.0342(10) Uani 1 1 d . . . . .
H12 H 0.3030 0.6247 0.3672 0.041 Uiso 1 1 calc R . . . .
C6 C 0.8077(5) 0.7324(3) 0.5592(3) 0.0365(10) Uani 1 1 d . . . . .
C1 C 0.6649(5) 0.7706(3) 0.5454(3) 0.0411(11) Uani 1 1 d . . . . .
C17 C 0.7520(5) 0.4950(3) 0.4072(2) 0.0324(10) Uani 1 1 d . . . . .
C13 C 0.3150(5) 0.5161(4) 0.2800(3) 0.0400(11) Uani 1 1 d . . . . .
N3 N 0.8257(6) 0.2231(4) 0.5762(4) 0.0763(16) Uani 1 1 d . . . . .
C8 C 0.7391(4) 0.5725(3) 0.4768(2) 0.0292(9) Uani 1 1 d . . . . .
H8 H 0.7648 0.5322 0.5279 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6024(5) 0.7411(3) 0.4608(3) 0.0396(11) Uani 1 1 d . . . . .
H10 H 0.5157 0.7843 0.4349 0.048 Uiso 1 1 calc R . . . .
C18 C 0.8686(5) 0.5286(4) 0.3642(3) 0.0441(11) Uani 1 1 d . . . . .
H18A H 0.8703 0.4769 0.3213 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.9624 0.5282 0.4010 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.8484 0.6024 0.3425 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.4021(5) 0.4449(4) 0.2492(3) 0.0441(11) Uani 1 1 d . . . . .
H14 H 0.3648 0.4041 0.2028 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8960(5) 0.7371(3) 0.6337(3) 0.0425(11) Uani 1 1 d . . . . .
H5 H 0.9921 0.7105 0.6429 0.051 Uiso 1 1 calc R . . . .
N1 N 0.7950(6) 0.3832(4) 0.4376(3) 0.0642(14) Uani 1 1 d . . . . .
C15 C 0.5463(5) 0.4346(4) 0.2880(3) 0.0388(10) Uani 1 1 d . . . . .
C7 C 0.8225(5) 0.6825(3) 0.4822(3) 0.0358(10) Uani 1 1 d . . . . .
H7 H 0.9233 0.6773 0.4741 0.043 Uiso 1 1 calc R . . . .
C2 C 0.6090(6) 0.8140(4) 0.6056(4) 0.0567(15) Uani 1 1 d . . . . .
H2 H 0.5125 0.8397 0.5963 0.068 Uiso 1 1 calc R . . . .
C22 C 0.8515(6) 0.0303(4) 0.5611(3) 0.0500(13) Uani 1 1 d . . . . .
H22 H 0.8734 -0.0393 0.5851 0.060 Uiso 1 1 calc R . . . .
C4 C 0.8411(6) 0.7810(4) 0.6940(3) 0.0519(13) Uani 1 1 d . . . . .
H4 H 0.9005 0.7855 0.7452 0.062 Uiso 1 1 calc R . . . .
C21 C 0.8126(6) 0.0406(4) 0.4814(3) 0.0560(14) Uani 1 1 d . . . . .
H21 H 0.8044 -0.0221 0.4485 0.067 Uiso 1 1 calc R . . . .
C3 C 0.6984(6) 0.8194(4) 0.6808(4) 0.0598(15) Uani 1 1 d . . . . .
H3 H 0.6623 0.8491 0.7232 0.072 Uiso 1 1 calc R . . . .
C19 C 0.7894(6) 0.2286(4) 0.4984(4) 0.0615(16) Uani 1 1 d . . . . .
C20 C 0.7856(7) 0.1431(5) 0.4497(4) 0.0678(17) Uani 1 1 d . . . . .
H20 H 0.7647 0.1533 0.3943 0.081 Uiso 1 1 calc R . . . .
C23 C 0.8580(7) 0.1240(5) 0.6056(4) 0.0700(18) Uani 1 1 d . . . . .
H23 H 0.8875 0.1171 0.6610 0.084 Uiso 1 1 calc R . . . .
N2 N 0.7495(8) 0.3400(5) 0.4714(6) 0.146(4) Uani 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
Cl1 C13 1.735(5) . ?
Cl2 C15 1.743(5) . ?
O1 C10 1.436(5) . ?
O1 C7 1.463(5) . ?
C11 C9 1.499(6) . ?
C11 C16 1.396(6) . ?
C11 C12 1.392(6) . ?
C9 H9 1.0000 . ?
C9 C8 1.559(5) . ?
C9 C10 1.569(5) . ?
C16 C17 1.517(6) . ?
C16 C15 1.391(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(6) . ?
C6 C1 1.407(6) . ?
C6 C5 1.387(6) . ?
C6 C7 1.506(6) . ?
C1 C10 1.508(7) . ?
C1 C2 1.379(7) . ?
C17 C8 1.562(6) . ?
C17 C18 1.522(6) . ?
C17 N1 1.489(6) . ?
C13 C14 1.385(7) . ?
N3 C19 1.326(8) . ?
N3 C23 1.323(7) . ?
C8 H8 1.0000 . ?
C8 C7 1.552(6) . ?
C10 H10 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.398(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(7) . ?
N1 N2 0.959(6) . ?
C7 H7 1.0000 . ?
C2 H2 0.9500 . ?
C2 C3 1.401(8) . ?
C22 H22 0.9500 . ?
C22 C21 1.363(8) . ?
C22 C23 1.375(8) . ?
C4 H4 0.9500 . ?
C4 C3 1.407(8) . ?
C21 H21 0.9500 . ?
C21 C20 1.368(8) . ?
C3 H3 0.9500 . ?
C19 C20 1.341(9) . ?
C19 N2 1.462(7) . ?
C20 H20 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C7 96.7(3) . . ?
C16 C11 C9 111.8(4) . . ?
C12 C11 C9 126.4(4) . . ?
C12 C11 C16 121.8(4) . . ?
C11 C9 H9 111.5 . . ?
C11 C9 C8 104.8(3) . . ?
C11 C9 C10 115.5(3) . . ?
C8 C9 H9 111.5 . . ?
C8 C9 C10 101.3(3) . . ?
C10 C9 H9 111.5 . . ?
C11 C16 C17 111.9(4) . . ?
C15 C16 C11 118.4(4) . . ?
C15 C16 C17 129.7(4) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.9(4) . . ?
C13 C12 H12 121.1 . . ?
C1 C6 C7 104.6(4) . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 C7 134.1(4) . . ?
C6 C1 C10 104.6(4) . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 C10 134.3(4) . . ?
C16 C17 C8 103.9(3) . . ?
C16 C17 C18 114.0(4) . . ?
C18 C17 C8 113.9(4) . . ?
N1 C17 C16 110.9(4) . . ?
N1 C17 C8 109.9(4) . . ?
N1 C17 C18 104.4(4) . . ?
C12 C13 Cl1 118.8(4) . . ?
C12 C13 C14 122.6(4) . . ?
C14 C13 Cl1 118.6(4) . . ?
C23 N3 C19 115.4(5) . . ?
C9 C8 C17 107.6(3) . . ?
C9 C8 H8 110.3 . . ?
C17 C8 H8 110.3 . . ?
C7 C8 C9 101.2(3) . . ?
C7 C8 C17 116.6(3) . . ?
C7 C8 H8 110.3 . . ?
O1 C10 C9 101.7(3) . . ?
O1 C10 C1 102.7(4) . . ?
O1 C10 H10 115.4 . . ?
C9 C10 H10 115.4 . . ?
C1 C10 C9 104.3(3) . . ?
C1 C10 H10 115.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(4) . . ?
C15 C14 H14 120.8 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.5(5) . . ?
C4 C5 H5 120.8 . . ?
N2 N1 C17 126.6(6) . . ?
C16 C15 Cl2 122.3(3) . . ?
C16 C15 C14 120.9(4) . . ?
C14 C15 Cl2 116.7(3) . . ?
O1 C7 C6 102.2(3) . . ?
O1 C7 C8 101.7(3) . . ?
O1 C7 H7 115.3 . . ?
C6 C7 C8 105.1(3) . . ?
C6 C7 H7 115.3 . . ?
C8 C7 H7 115.3 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C21 C22 H22 121.1 . . ?
C21 C22 C23 117.8(5) . . ?
C23 C22 H22 121.1 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C22 C21 H21 120.6 . . ?
C22 C21 C20 118.8(5) . . ?
C20 C21 H21 120.6 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N3 C19 C20 124.9(5) . . ?
N3 C19 N2 111.7(7) . . ?
C20 C19 N2 123.4(7) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 C21 118.6(6) . . ?
C19 C20 H20 120.7 . . ?
N3 C23 C22 124.3(6) . . ?
N3 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
N1 N2 C19 126.1(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.726
####################################################################### 
# 
# 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_cmrv-ad-678_mo
_database_code_depnum_ccdc_archive 'CCDC 1981051'
loop_
_audit_author_name
_audit_author_address
'Arnab Dey'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N3 O'
_chemical_formula_sum            'C25 H19 N3 O'
_chemical_formula_weight         377.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.2254(15)
_cell_length_b                   10.4986(11)
_cell_length_c                   15.5704(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.455(12)
_cell_angle_gamma                90
_cell_volume                     1943.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6020
_cell_measurement_theta_min      2.3800
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.1603
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6311
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.361
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  63.00   0.50   16.00    --  -20.00   0.00-108.00  346
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262643000
_diffrn_orient_matrix_UB_12      -0.0306507000
_diffrn_orient_matrix_UB_13      -0.0400894000
_diffrn_orient_matrix_UB_21      -0.0522390000
_diffrn_orient_matrix_UB_22      0.0018319000
_diffrn_orient_matrix_UB_23      0.0124250000
_diffrn_orient_matrix_UB_31      -0.0118129000
_diffrn_orient_matrix_UB_32      0.0601903000
_diffrn_orient_matrix_UB_33      -0.0207841000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1945
_reflns_number_total             3354
_reflns_odcompleteness_completeness 83.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.97
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      1.033
_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)+(0.0756P)²+0.6595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.2083
_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:
 C16(H16), C21(H21), C17(H17), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C23(H23), C11(H11), C1(H1), C14(H14), C22(H22), C5(H5), C24(H24),
 C4(H4), C25(H25), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
O1 O 1.0322(2) 0.7607(2) 0.39722(15) 0.0295(6) Uani 1 1 d . . . . .
N2 N 0.6746(3) 0.8039(3) 0.4319(2) 0.0312(8) Uani 1 1 d . . . . .
N1 N 0.6211(3) 0.8406(3) 0.3583(2) 0.0322(8) Uani 1 1 d . . . . .
N3 N 0.8157(3) 0.1226(3) 0.4082(2) 0.0421(9) Uani 1 1 d . . . . .
C16 C 0.8654(3) 0.6765(3) 0.3131(2) 0.0262(9) Uani 1 1 d . . . . .
H16 H 0.8207 0.6668 0.2525 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7726(3) 0.5516(3) 0.5078(2) 0.0337(10) Uani 1 1 d . . . . .
H10 H 0.7487 0.5877 0.5549 0.040 Uiso 1 1 calc R . . . .
C7 C 0.7970(3) 0.7727(3) 0.4388(2) 0.0263(8) Uani 1 1 d . . . . .
C21 C 0.9919(3) 0.6894(3) 0.3170(2) 0.0294(9) Uani 1 1 d . . . . .
H21 H 1.0311 0.6087 0.3138 0.035 Uiso 1 1 calc R . . . .
C23 C 1.0244(3) 0.8926(4) 0.1173(3) 0.0438(11) Uani 1 1 d . . . . .
H23 H 1.0405 0.8905 0.0618 0.053 Uiso 1 1 calc R . . . .
C8 C 0.8581(3) 0.8350(3) 0.5251(2) 0.0329(9) Uani 1 1 d . . . . .
H8A H 0.8494 0.9257 0.5202 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.9366 0.8137 0.5371 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.8268 0.8047 0.5725 0.049 Uiso 1 1 calc GR . . . .
C19 C 0.9792(3) 0.9031(3) 0.2833(2) 0.0290(9) Uani 1 1 d . . . . .
C9 C 0.8026(3) 0.6284(3) 0.4446(2) 0.0277(9) Uani 1 1 d . . . . .
C15 C 0.8383(3) 0.5757(3) 0.3741(2) 0.0279(9) Uani 1 1 d . . . . .
C17 C 0.8411(3) 0.8056(3) 0.3554(2) 0.0278(9) Uani 1 1 d . . . . .
H17 H 0.7854 0.8557 0.3134 0.033 Uiso 1 1 calc R . . . .
C13 C 0.8169(3) 0.2322(4) 0.4193(2) 0.0321(9) Uani 1 1 d . . . . .
C11 C 0.7786(3) 0.4201(3) 0.4999(2) 0.0325(9) Uani 1 1 d . . . . .
H11 H 0.7591 0.3673 0.5419 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5035(3) 0.8673(3) 0.3558(3) 0.0326(9) Uani 1 1 d . . . . .
C1 C 0.4445(3) 0.8921(4) 0.2772(2) 0.0440(11) Uani 1 1 d . . . . .
H1 H 0.4764 0.8910 0.2285 0.053 Uiso 1 1 calc R . . . .
C18 C 0.9577(3) 0.8691(3) 0.3725(2) 0.0286(9) Uani 1 1 d . . . . .
H18 H 0.9693 0.9389 0.4155 0.034 Uiso 1 1 calc R . . . .
C20 C 1.0028(3) 0.7870(3) 0.2471(2) 0.0297(9) Uani 1 1 d . . . . .
C14 C 0.8458(3) 0.4450(3) 0.3658(2) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.8714 0.4094 0.3193 0.037 Uiso 1 1 calc R . . . .
C12 C 0.8140(3) 0.3682(3) 0.4290(2) 0.0265(8) Uani 1 1 d . . . . .
C22 C 1.0250(3) 0.7799(4) 0.1650(3) 0.0404(10) Uani 1 1 d . . . . .
H22 H 1.0401 0.7021 0.1416 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4607(4) 0.8722(4) 0.4297(3) 0.0443(11) Uani 1 1 d . . . . .
H5 H 0.5063 0.8566 0.4854 0.053 Uiso 1 1 calc R . . . .
C24 C 1.0000(4) 1.0078(4) 0.1523(3) 0.0436(11) Uani 1 1 d . . . . .
H24 H 0.9998 1.0820 0.1197 0.052 Uiso 1 1 calc R . . . .
C4 C 0.3476(4) 0.9012(4) 0.4194(3) 0.0522(13) Uani 1 1 d . . . . .
H4 H 0.3156 0.9044 0.4680 0.063 Uiso 1 1 calc R . . . .
C25 C 0.9757(3) 1.0146(4) 0.2354(3) 0.0382(10) Uani 1 1 d . . . . .
H25 H 0.9578 1.0919 0.2579 0.046 Uiso 1 1 calc R . . . .
C3 C 0.2850(4) 0.9248(5) 0.3372(3) 0.0560(13) Uani 1 1 d . . . . .
H3 H 0.2089 0.9442 0.3272 0.067 Uiso 1 1 calc R . . . .
C2 C 0.3385(5) 0.9188(6) 0.2693(4) 0.090(2) Uani 1 1 d . . . . .
H2 H 0.2957 0.9352 0.2128 0.108 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
O1 C21 1.441(4) . ?
O1 C18 1.453(4) . ?
N2 N1 1.241(4) . ?
N2 C7 1.510(4) . ?
N1 C6 1.457(5) . ?
N3 C13 1.163(4) . ?
C16 H16 0.9800 . ?
C16 C21 1.540(5) . ?
C16 C15 1.511(5) . ?
C16 C17 1.565(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.386(5) . ?
C10 C11 1.390(5) . ?
C7 C8 1.525(5) . ?
C7 C9 1.518(5) . ?
C7 C17 1.557(5) . ?
C21 H21 0.9800 . ?
C21 C20 1.523(5) . ?
C23 H23 0.9300 . ?
C23 C22 1.395(5) . ?
C23 C24 1.387(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C19 C18 1.514(5) . ?
C19 C20 1.402(5) . ?
C19 C25 1.384(5) . ?
C9 C15 1.387(5) . ?
C15 C14 1.383(5) . ?
C17 H17 0.9800 . ?
C17 C18 1.540(5) . ?
C13 C12 1.437(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C6 C1 1.294(5) . ?
C6 C5 1.372(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.304(6) . ?
C18 H18 0.9800 . ?
C20 C22 1.369(5) . ?
C14 H14 0.9300 . ?
C14 C12 1.396(5) . ?
C22 H22 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.388(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.394(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.352(6) . ?
C25 H25 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.367(6) . ?
C2 H2 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
C21 O1 C18 96.3(2) . . ?
N1 N2 C7 115.7(3) . . ?
N2 N1 C6 112.9(3) . . ?
C21 C16 H16 112.2 . . ?
C21 C16 C17 101.2(3) . . ?
C15 C16 H16 112.2 . . ?
C15 C16 C21 113.7(3) . . ?
C15 C16 C17 104.5(3) . . ?
C17 C16 H16 112.2 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.1(3) . . ?
C11 C10 H10 120.4 . . ?
N2 C7 C8 104.1(3) . . ?
N2 C7 C9 104.5(3) . . ?
N2 C7 C17 114.9(3) . . ?
C8 C7 C17 116.5(3) . . ?
C9 C7 C8 111.7(3) . . ?
C9 C7 C17 104.5(3) . . ?
O1 C21 C16 102.6(3) . . ?
O1 C21 H21 114.9 . . ?
O1 C21 C20 101.6(3) . . ?
C16 C21 H21 114.9 . . ?
C20 C21 C16 106.6(3) . . ?
C20 C21 H21 114.9 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C24 C23 C22 120.3(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C20 C19 C18 105.1(3) . . ?
C25 C19 C18 134.8(3) . . ?
C25 C19 C20 120.1(3) . . ?
C10 C9 C7 127.3(3) . . ?
C10 C9 C15 120.9(3) . . ?
C15 C9 C7 111.7(3) . . ?
C9 C15 C16 111.9(3) . . ?
C14 C15 C16 127.4(3) . . ?
C14 C15 C9 120.7(3) . . ?
C16 C17 H17 110.7 . . ?
C7 C17 C16 107.2(3) . . ?
C7 C17 H17 110.7 . . ?
C18 C17 C16 100.9(3) . . ?
C18 C17 C7 116.0(3) . . ?
C18 C17 H17 110.7 . . ?
N3 C13 C12 177.2(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C1 C6 N1 113.2(3) . . ?
C1 C6 C5 123.2(4) . . ?
C5 C6 N1 123.5(4) . . ?
C6 C1 H1 121.4 . . ?
C6 C1 C2 117.1(4) . . ?
C2 C1 H1 121.4 . . ?
O1 C18 C19 101.3(3) . . ?
O1 C18 C17 101.8(3) . . ?
O1 C18 H18 115.0 . . ?
C19 C18 C17 107.2(3) . . ?
C19 C18 H18 115.0 . . ?
C17 C18 H18 115.0 . . ?
C19 C20 C21 103.7(3) . . ?
C22 C20 C21 134.4(3) . . ?
C22 C20 C19 121.8(3) . . ?
C15 C14 H14 120.9 . . ?
C15 C14 C12 118.1(3) . . ?
C12 C14 H14 120.9 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 C14 121.6(3) . . ?
C14 C12 C13 118.9(3) . . ?
C23 C22 H22 120.9 . . ?
C20 C22 C23 118.2(4) . . ?
C20 C22 H22 120.9 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C23 C24 H24 119.3 . . ?
C23 C24 C25 121.4(4) . . ?
C25 C24 H24 119.3 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C19 C25 C24 118.1(4) . . ?
C19 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C4 C3 H3 121.4 . . ?
C4 C3 C2 117.1(5) . . ?
C2 C3 H3 121.4 . . ?
C1 C2 C3 125.5(5) . . ?
C1 C2 H2 117.2 . . ?
C3 C2 H2 117.2 . . ?

_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 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.728
####################################################################### 
# 
# 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_cmrv-ad-788_mo
_database_code_depnum_ccdc_archive 'CCDC 1981053'
loop_
_audit_author_name
_audit_author_address
'Arnab Dey'
;IIT Bombay
India
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N3 O3'
_chemical_formula_sum            'C25 H21 N3 O3'
_chemical_formula_weight         411.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   15.931(3)
_cell_length_b                   10.1424(14)
_cell_length_c                   12.3571(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.839(13)
_cell_angle_gamma                90
_cell_volume                     1992.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.5730
_cell_measurement_theta_min      2.3730
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.1454
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8562
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_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    -59.00  49.00   0.50    8.00    --  -20.00  72.00  36.00  216
  2  ω    -68.50   0.00   0.50    8.00    --  -20.00 -72.00-180.00  137
  3  ω    -14.50  45.50   0.50    8.00    --  -20.00  72.00 108.00  120
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0403119000
_diffrn_orient_matrix_UB_12      -0.0246206000
_diffrn_orient_matrix_UB_13      -0.0175959000
_diffrn_orient_matrix_UB_21      0.0160580000
_diffrn_orient_matrix_UB_22      -0.0653208000
_diffrn_orient_matrix_UB_23      0.0039912000
_diffrn_orient_matrix_UB_31      -0.0109953000
_diffrn_orient_matrix_UB_32      -0.0032214000
_diffrn_orient_matrix_UB_33      0.0544881000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1488
_reflns_number_total             3482
_reflns_odcompleteness_completeness 88.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.14
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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         0.314
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0887
_refine_ls_restrained_S_all      0.990
_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)+(0.1453P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.3144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C20(H20), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C21(H21), C3(H3), C1(H1), C13(H13), C14(H14), C15(H15),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_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
O1 O 0.1453(3) 0.6139(4) 0.4942(3) 0.0708(12) Uani 1 1 d . . . . .
N1 N 0.4597(3) 0.2052(4) 0.2925(3) 0.0553(12) Uani 1 1 d . . . . .
O4 O 0.4027(3) 0.5913(4) 0.8525(3) 0.0845(14) Uani 1 1 d . . . . .
N2 N 0.3455(3) 0.3428(4) 0.2926(3) 0.0547(12) Uani 1 1 d . . . . .
N3 N 0.2867(3) 0.3915(4) 0.2401(3) 0.0602(13) Uani 1 1 d . . . . .
O5 O 0.2977(3) 0.4673(5) 0.9215(3) 0.0877(15) Uani 1 1 d . . . . .
C5 C 0.3988(3) 0.2637(5) 0.2312(4) 0.0471(13) Uani 1 1 d . . . . .
C6 C 0.2290(3) 0.4785(5) 0.3005(4) 0.0487(13) Uani 1 1 d . . . . .
C4 C 0.3892(3) 0.2513(5) 0.1195(4) 0.0557(15) Uani 1 1 d . . . . .
H4 H 0.344097 0.293273 0.078801 0.067 Uiso 1 1 calc R . . . .
C8 C 0.2455(3) 0.4724(5) 0.4262(4) 0.0481(13) Uani 1 1 d . . . . .
H8 H 0.300756 0.429230 0.446602 0.058 Uiso 1 1 calc R . . . .
C11 C 0.1408(4) 0.4202(5) 0.2788(4) 0.0556(15) Uani 1 1 d . . . . .
C2 C 0.5116(3) 0.1134(5) 0.1306(4) 0.0574(15) Uani 1 1 d . . . . .
H2 H 0.551970 0.060906 0.097341 0.069 Uiso 1 1 calc R . . . .
C22 C 0.3398(4) 0.5671(5) 0.7721(4) 0.0604(16) Uani 1 1 d . . . . .
C19 C 0.2643(4) 0.5796(5) 0.6043(4) 0.0579(15) Uani 1 1 d . . . . .
C21 C 0.3364(4) 0.6111(5) 0.6661(4) 0.0571(15) Uani 1 1 d . . . . .
H21 H 0.380943 0.659800 0.637822 0.068 Uiso 1 1 calc R . . . .
C3 C 0.4474(3) 0.1761(5) 0.0694(4) 0.0600(15) Uani 1 1 d . . . . .
H3 H 0.443450 0.167148 -0.007266 0.072 Uiso 1 1 calc R . . . .
C1 C 0.5149(4) 0.1299(5) 0.2415(4) 0.0607(16) Uani 1 1 d . . . . .
H1 H 0.558157 0.086234 0.284254 0.073 Uiso 1 1 calc R . . . .
C9 C 0.1706(3) 0.3911(5) 0.4706(4) 0.0505(13) Uani 1 1 d . . . . .
H9 H 0.189888 0.307245 0.506891 0.061 Uiso 1 1 calc R . . . .
C10 C 0.1100(3) 0.3676(5) 0.3739(4) 0.0571(15) Uani 1 1 d . . . . .
C13 C 0.0161(4) 0.3461(7) 0.1790(5) 0.0767(19) Uani 1 1 d . . . . .
H13 H -0.016932 0.335727 0.112700 0.092 Uiso 1 1 calc R . . . .
C20 C 0.2373(4) 0.6040(5) 0.4875(4) 0.0599(15) Uani 1 1 d . . . . .
H20 H 0.264218 0.681636 0.454026 0.072 Uiso 1 1 calc R . . . .
C12 C 0.0913(4) 0.4116(5) 0.1793(4) 0.0627(16) Uani 1 1 d . . . . .
C18 C 0.2006(4) 0.5066(5) 0.6461(4) 0.0589(15) Uani 1 1 d . . . . .
C17 C 0.1346(4) 0.4911(6) 0.5510(4) 0.0650(16) Uani 1 1 d . . . . .
H17 H 0.076130 0.472462 0.571608 0.078 Uiso 1 1 calc R . . . .
C14 C -0.0123(4) 0.2953(7) 0.2721(5) 0.084(2) Uani 1 1 d . . . . .
H14 H -0.065416 0.252436 0.269259 0.101 Uiso 1 1 calc R . . . .
C23 C 0.2777(4) 0.4961(6) 0.8143(5) 0.0677(17) Uani 1 1 d . . . . .
C15 C 0.0343(4) 0.3044(6) 0.3708(5) 0.0733(18) Uani 1 1 d . . . . .
H15 H 0.013872 0.267575 0.434670 0.088 Uiso 1 1 calc R . . . .
C7 C 0.2441(4) 0.6156(5) 0.2520(4) 0.0674(17) Uani 1 1 d . . . . .
H7A H 0.298307 0.650081 0.281747 0.101 Uiso 1 1 calc GR . . . .
H7B H 0.198972 0.675555 0.270400 0.101 Uiso 1 1 calc GR . . . .
H7C H 0.244698 0.608459 0.172958 0.101 Uiso 1 1 calc GR . . . .
C24 C 0.2056(4) 0.4596(6) 0.7541(4) 0.0736(18) Uani 1 1 d . . . . .
H24 H 0.162757 0.407403 0.782691 0.088 Uiso 1 1 calc R . . . .
C16 C 0.1188(4) 0.4681(6) 0.0727(4) 0.0760(19) Uani 1 1 d . . . . .
H16A H 0.110360 0.563807 0.071928 0.114 Uiso 1 1 calc GR . . . .
H16B H 0.085203 0.428268 0.011887 0.114 Uiso 1 1 calc GR . . . .
H16C H 0.178433 0.448459 0.065926 0.114 Uiso 1 1 calc GR . . . .
C25 C 0.3744(5) 0.5288(7) 0.9466(5) 0.088(2) Uani 1 1 d . . . . .
H25A H 0.416363 0.462730 0.973967 0.105 Uiso 1 1 calc R . . . .
H25B H 0.368144 0.595147 1.004217 0.105 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
O1 C20 1.477(7) . ?
O1 C17 1.445(6) . ?
N1 C5 1.329(5) . ?
N1 C1 1.351(7) . ?
O4 C22 1.384(6) . ?
O4 C25 1.424(7) . ?
N2 N3 1.208(5) . ?
N2 C5 1.424(6) . ?
N3 C6 1.508(6) . ?
O5 C23 1.372(7) . ?
O5 C25 1.387(8) . ?
C5 C4 1.384(6) . ?
C6 C8 1.559(7) . ?
C6 C11 1.531(7) . ?
C6 C7 1.539(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.380(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.579(7) . ?
C8 C20 1.545(7) . ?
C11 C10 1.409(7) . ?
C11 C12 1.419(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(7) . ?
C2 C1 1.377(7) . ?
C22 C21 1.381(7) . ?
C22 C23 1.356(8) . ?
C19 C21 1.374(7) . ?
C19 C20 1.499(7) . ?
C19 C18 1.383(8) . ?
C21 H21 0.9500 . ?
C3 H3 0.9500 . ?
C1 H1 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.504(7) . ?
C9 C17 1.557(7) . ?
C10 C15 1.364(7) . ?
C13 H13 0.9500 . ?
C13 C12 1.369(8) . ?
C13 C14 1.365(8) . ?
C20 H20 1.0000 . ?
C12 C16 1.527(7) . ?
C18 C17 1.531(7) . ?
C18 C24 1.415(7) . ?
C17 H17 1.0000 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(8) . ?
C23 C24 1.378(9) . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C24 H24 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

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
C17 O1 C20 96.7(4) . . ?
C5 N1 C1 117.3(4) . . ?
C22 O4 C25 104.7(5) . . ?
N3 N2 C5 114.4(4) . . ?
N2 N3 C6 116.8(4) . . ?
C23 O5 C25 105.3(5) . . ?
N1 C5 N2 112.8(4) . . ?
N1 C5 C4 123.7(5) . . ?
C4 C5 N2 123.5(4) . . ?
N3 C6 C8 113.7(4) . . ?
N3 C6 C11 105.7(4) . . ?
N3 C6 C7 102.7(4) . . ?
C11 C6 C8 104.5(4) . . ?
C11 C6 C7 116.5(4) . . ?
C7 C6 C8 113.8(4) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 H4 121.1 . . ?
C6 C8 H8 110.9 . . ?
C6 C8 C9 106.6(4) . . ?
C9 C8 H8 110.9 . . ?
C20 C8 C6 116.1(4) . . ?
C20 C8 H8 110.9 . . ?
C20 C8 C9 100.9(4) . . ?
C10 C11 C6 111.6(4) . . ?
C10 C11 C12 119.7(5) . . ?
C12 C11 C6 128.7(5) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.7(5) . . ?
C21 C22 O4 127.1(6) . . ?
C23 C22 O4 109.2(5) . . ?
C23 C22 C21 123.6(5) . . ?
C21 C19 C20 132.3(6) . . ?
C21 C19 C18 121.6(5) . . ?
C18 C19 C20 106.1(5) . . ?
C22 C21 H21 122.3 . . ?
C19 C21 C22 115.5(6) . . ?
C19 C21 H21 122.3 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N1 C1 C2 123.3(5) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C8 C9 H9 112.5 . . ?
C10 C9 C8 105.5(4) . . ?
C10 C9 H9 112.5 . . ?
C10 C9 C17 111.5(4) . . ?
C17 C9 C8 101.6(4) . . ?
C17 C9 H9 112.5 . . ?
C11 C10 C9 111.2(5) . . ?
C15 C10 C11 120.7(5) . . ?
C15 C10 C9 128.1(5) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.4(6) . . ?
O1 C20 C8 101.7(4) . . ?
O1 C20 C19 100.4(5) . . ?
O1 C20 H20 115.1 . . ?
C8 C20 H20 115.1 . . ?
C19 C20 C8 107.6(4) . . ?
C19 C20 H20 115.1 . . ?
C11 C12 C16 123.3(6) . . ?
C13 C12 C11 117.8(6) . . ?
C13 C12 C16 118.8(5) . . ?
C19 C18 C17 104.6(5) . . ?
C19 C18 C24 122.4(5) . . ?
C24 C18 C17 132.9(6) . . ?
O1 C17 C9 101.0(4) . . ?
O1 C17 C18 100.8(4) . . ?
O1 C17 H17 115.4 . . ?
C9 C17 H17 115.4 . . ?
C18 C17 C9 107.0(4) . . ?
C18 C17 H17 115.4 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.8(6) . . ?
C15 C14 H14 119.1 . . ?
O5 C23 C24 126.6(6) . . ?
C22 C23 O5 110.9(5) . . ?
C22 C23 C24 122.6(5) . . ?
C10 C15 C14 118.4(6) . . ?
C10 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C18 C24 H24 122.9 . . ?
C23 C24 C18 114.3(6) . . ?
C23 C24 H24 122.9 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C25 H25A 109.7 . . ?
O4 C25 H25B 109.7 . . ?
O5 C25 O4 109.8(5) . . ?
O5 C25 H25A 109.7 . . ?
O5 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?

_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 6.004
_oxdiff_exptl_absorpt_empirical_full_min 0.548
