# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_srk-ps-01-40_mo
_audit_block_doi                 10.5517/ccdc.csd.cc1yzn1m
_database_code_depnum_ccdc_archive 'CCDC 1816911'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;
_audit_creation_date             2017-12-18
_audit_creation_method           
;
Olex2 1.2
(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 H23 N O2'
_chemical_formula_sum            'C24 H23 N O2'
_chemical_formula_weight         357.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.7181(7)
_cell_length_b                   10.2605(5)
_cell_length_c                   12.0651(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1822.01(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6356
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.8070
_cell_measurement_theta_min      2.5880
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13659
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.606
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.50  19.00   0.50   10.00    --  -20.00 -72.00  36.00  223
  2  ω    -41.00  40.00   0.50   10.00    --  -20.00  72.00-180.00  162
  3  ω    -93.50 -17.00   0.50   10.00    --  -20.00 -72.00 -36.00  153
  4  ω    -59.00  49.00   0.50   10.00    --  -20.00  72.00  36.00  216
  5  ω    -47.50  -4.00   0.50   10.00    --  -20.00  72.00 108.00   87
;
_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      0.0386701000
_diffrn_orient_matrix_UB_12      -0.0150153000
_diffrn_orient_matrix_UB_13      0.0327321000
_diffrn_orient_matrix_UB_21      -0.0282245000
_diffrn_orient_matrix_UB_22      -0.0070560000
_diffrn_orient_matrix_UB_23      0.0472067000
_diffrn_orient_matrix_UB_31      -0.0057321000
_diffrn_orient_matrix_UB_32      -0.0670822000
_diffrn_orient_matrix_UB_33      -0.0124652000
_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                1412
_reflns_number_total             1696
_reflns_odcompleteness_completeness 93.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.24
_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         0.305
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.060
_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)+(0.0690P)²+0.6300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1319
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C14(H14), C3(H3), C2(H2), C6(H6), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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 0.71575(8) 0.47176(11) 0.68352(9) 0.0304(4) Uani 1 1 d . . . . .
N1 N 0.71855(12) 0.2500 0.70848(15) 0.0214(5) Uani 1 2 d S T P . .
C9 C 0.79740(10) 0.38718(16) 0.46621(13) 0.0239(4) Uani 1 1 d . . . . .
H9A H 0.7889 0.3861 0.3848 0.029 Uiso 1 1 calc R . . . .
H9B H 0.8033 0.4791 0.4900 0.029 Uiso 1 1 calc R . . . .
C10 C 0.88254(11) 0.31445(17) 0.49539(13) 0.0275(4) Uani 1 1 d . . . . .
H10 H 0.9363 0.3609 0.5138 0.033 Uiso 1 1 calc R . . . .
C12 C 0.54677(10) 0.31493(16) 0.54191(12) 0.0224(4) Uani 1 1 d . . . . .
H12 H 0.5031 0.3652 0.5811 0.027 Uiso 1 1 calc R . . . .
C14 C 0.52834(12) 0.38746(17) 0.30155(13) 0.0278(4) Uani 1 1 d . . . . .
H14 H 0.4708 0.3673 0.3328 0.033 Uiso 1 1 calc R . . . .
C7 C 0.71619(10) 0.36288(15) 0.64529(13) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.71378(10) 0.32557(15) 0.52263(12) 0.0195(4) Uani 1 1 d . . . . .
C13 C 0.61107(11) 0.32659(15) 0.35321(12) 0.0225(4) Uani 1 1 d . . . . .
H13 H 0.6654 0.3564 0.3104 0.027 Uiso 1 1 calc R . . . .
C3 C 0.79981(17) 0.2500 0.9984(2) 0.0284(6) Uani 1 2 d S T P . .
H3 H 0.8557 0.2500 1.0379 0.034 Uiso 1 2 calc RS T P . .
C1 C 0.71870(14) 0.2500 0.82774(18) 0.0206(5) Uani 1 2 d S T P . .
C11 C 0.62187(10) 0.37506(15) 0.47454(12) 0.0210(4) Uani 1 1 d . . . . .
H11 H 0.6186 0.4723 0.4779 0.025 Uiso 1 1 calc R . . . .
C2 C 0.80026(15) 0.2500 0.88370(19) 0.0260(5) Uani 1 2 d S T P . .
H2 H 0.8561 0.2500 0.8441 0.031 Uiso 1 2 calc RS T P . .
C6 C 0.63696(15) 0.2500 0.88392(19) 0.0246(5) Uani 1 2 d S T P . .
H6 H 0.5812 0.2500 0.8443 0.030 Uiso 1 2 calc RS T P . .
C4 C 0.71886(16) 0.2500 1.0556(2) 0.0270(6) Uani 1 2 d S T P . .
H4 H 0.7191 0.2500 1.1344 0.032 Uiso 1 2 calc RS T P . .
C5 C 0.63727(16) 0.2500 0.99904(19) 0.0261(5) Uani 1 2 d S T P . .
H5 H 0.5815 0.2500 1.0387 0.031 Uiso 1 2 calc RS T P . .
C15 C 0.53043(16) 0.46664(19) 0.21607(16) 0.0381(5) Uani 1 1 d . . . . .
H15A H 0.4730(14) 0.503(2) 0.1852(17) 0.048(6) Uiso 1 1 d . . . . .
H15B H 0.5879(17) 0.487(2) 0.1820(18) 0.057(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2086(19) . ?
N1 C7 1.3871(18) . ?
N1 C7 1.3871(18) 7_565 ?
N1 C1 1.439(3) . ?
C9 C10 1.500(2) . ?
C9 C8 1.542(2) . ?
C10 C10 1.323(3) 7_565 ?
C12 C12 1.332(3) 7_565 ?
C12 C11 1.504(2) . ?
C14 C13 1.504(2) . ?
C14 C15 1.313(3) . ?
C7 C8 1.529(2) . ?
C8 C8 1.551(3) 7_565 ?
C8 C11 1.557(2) . ?
C13 C13 1.572(3) 7_565 ?
C13 C11 1.554(2) . ?
C3 C2 1.384(3) . ?
C3 C4 1.377(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.381(3) . ?
C6 C5 1.389(3) . ?
C4 C5 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C7 113.23(18) 7_565 . ?
C7 N1 C1 123.35(9) 7_565 . ?
C7 N1 C1 123.34(9) . . ?
C10 C9 C8 111.05(13) . . ?
C10 C10 C9 119.83(9) 7_565 . ?
C12 C12 C11 114.22(8) 7_565 . ?
C15 C14 C13 124.30(17) . . ?
O1 C7 N1 124.21(15) . . ?
O1 C7 C8 126.92(14) . . ?
N1 C7 C8 108.87(13) . . ?
C9 C8 C8 114.20(8) . 7_565 ?
C9 C8 C11 113.28(12) . . ?
C7 C8 C9 107.82(12) . . ?
C7 C8 C8 104.50(8) . 7_565 ?
C7 C8 C11 107.40(12) . . ?
C8 C8 C11 109.04(8) 7_565 . ?
C14 C13 C13 114.54(9) . 7_565 ?
C14 C13 C11 109.89(13) . . ?
C11 C13 C13 108.66(8) . 7_565 ?
C4 C3 C2 120.4(2) . . ?
C2 C1 N1 119.44(19) . . ?
C2 C1 C6 121.3(2) . . ?
C6 C1 N1 119.31(19) . . ?
C12 C11 C8 107.65(12) . . ?
C12 C11 C13 107.61(12) . . ?
C13 C11 C8 109.60(12) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C6 C5 119.2(2) . . ?
C3 C4 C5 120.3(2) . . ?
C4 C5 C6 119.8(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.980
_oxdiff_exptl_absorpt_empirical_full_min 0.475
