# 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_EXTER33
_audit_block_doi                 10.5517/ccdc.csd.cc2bd823
_database_code_depnum_ccdc_archive 'CCDC 2156734'
loop_
_audit_author_name
_audit_author_address
'VINAYKUMAR KANCHUPALLI'
;Inspire Faculty
India
;
_audit_update_record             
;
2022-03-07 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_audit_creation_date             2021-10-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_chemical_formula_moiety         'C22 H19 N O'
_chemical_formula_sum            'C22 H19 N O'
_chemical_formula_weight         313.40
_chemical_oxdiff_formula         'C H N O'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   16.6240(5)
_cell_length_b                   9.8728(3)
_cell_length_c                   19.5796(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3213.51(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9439
_cell_measurement_temperature    293(14)
_cell_measurement_theta_max      26.6330
_cell_measurement_theta_min      2.1010
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2955
_exptl_crystal_description       block
_exptl_crystal_F_000             1328.5591
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20142
_diffrn_reflns_theta_full        26.9910
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9680
_diffrn_measured_fraction_theta_max 0.9680
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -17.00   0.50   38.14    --   16.22 -79.00  57.00   80
  2  ω    -37.00  16.00   0.50   38.14    --  -14.97 -94.00  30.00  106
  3  ω     31.00  65.00   0.50   38.14    --   16.22-125.00  60.00   68
  4  ω    -17.00  57.00   0.50   38.14    --   16.22-102.00 -32.00  148
  5  ω    -64.00 -11.00   0.50   38.14    --  -14.97 125.00   0.00  106
  6  ω     -6.00  67.00   0.50   38.14    --   16.22  45.00 -90.00  146
  7  ω    -31.00  -6.00   0.50   38.14    --   16.22 -48.00-168.00   50
  8  ω    -33.00  16.00   0.50   38.14    --  -14.97 -94.00-180.00   98
  9  ω    -37.00  26.00   0.50   38.14    --   16.22 -94.00 -90.00  126
 10  ω    -67.00 -22.00   0.50   38.14    --  -14.97 125.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0389499000
_diffrn_orient_matrix_UB_12      -0.0015047000
_diffrn_orient_matrix_UB_13      -0.0147756000
_diffrn_orient_matrix_UB_21      0.0139290000
_diffrn_orient_matrix_UB_22      -0.0404236000
_diffrn_orient_matrix_UB_23      0.0275169000
_diffrn_orient_matrix_UB_31      -0.0104775000
_diffrn_orient_matrix_UB_32      -0.0593906000
_diffrn_orient_matrix_UB_33      -0.0183321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2353
_reflns_number_total             3391
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2144
_refine_diff_density_min         -0.2475
_refine_diff_density_rms         0.0602
_refine_ls_d_res_high            0.7830
_refine_ls_d_res_low             9.7898
_refine_ls_goodness_of_fit_ref   1.0241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.0241
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1226
_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 Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C13(H13), C10(H10), C2(H2), C12(H12), C11(H11), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
N1 N 0.62373(6) 0.44872(10) 0.49258(5) 0.0367(3) Uani 1.000000 .
O1 O 0.52471(8) 0.46192(11) 0.71915(6) 0.0745(4) Uani 1.000000 .
C7 C 0.67800(8) 0.55662(13) 0.50197(7) 0.0396(3) Uani 1.000000 .
C16 C 0.57400(8) 0.40414(13) 0.54536(7) 0.0360(3) Uani 1.000000 .
C14 C 0.61601(8) 0.60225(13) 0.61341(6) 0.0394(3) Uani 1.000000 .
C6 C 0.63834(8) 0.39233(13) 0.42731(6) 0.0392(3) Uani 1.000000 .
C9 C 0.67135(8) 0.63830(13) 0.56226(7) 0.0396(3) Uani 1.000000 .
C15 C 0.56957(8) 0.47704(14) 0.60458(7) 0.0388(3) Uani 1.000000 .
C17 C 0.53059(8) 0.27339(13) 0.53388(7) 0.0423(4) Uani 1.000000 .
H17a H 0.48489(8) 0.29055(13) 0.50432(7) 0.0508(4) Uiso 1.000000 R
H17b H 0.56633(8) 0.21195(13) 0.50994(7) 0.0508(4) Uiso 1.000000 R
C1 C 0.70426(8) 0.46303(16) 0.39968(7) 0.0456(4) Uani 1.000000 .
C20 C 0.51920(9) 0.42185(14) 0.66067(7) 0.0471(4) Uani 1.000000 .
C5 C 0.59822(9) 0.29443(15) 0.38893(7) 0.0468(4) Uani 1.000000 .
H5 H 0.55326(9) 0.25002(15) 0.40617(7) 0.0562(5) Uiso 1.000000 R
C18 C 0.50045(9) 0.20303(14) 0.59849(7) 0.0474(4) Uani 1.000000 .
C8 C 0.72759(9) 0.56504(16) 0.44679(8) 0.0487(4) Uani 1.000000 .
H8 H 0.76934(9) 0.62668(16) 0.44099(8) 0.0584(5) Uiso 1.000000 R
C13 C 0.60775(9) 0.68976(15) 0.66924(7) 0.0499(4) Uani 1.000000 .
H13 H 0.57060(9) 0.66941(15) 0.70324(7) 0.0599(5) Uiso 1.000000 R
C10 C 0.71738(9) 0.75613(15) 0.56927(8) 0.0523(4) Uani 1.000000 .
H10 H 0.75416(9) 0.77913(15) 0.53541(8) 0.0628(5) Uiso 1.000000 R
C19 C 0.46187(9) 0.31031(15) 0.64319(8) 0.0519(4) Uani 1.000000 .
H19a H 0.44277(9) 0.26854(15) 0.68500(8) 0.0623(5) Uiso 1.000000 R
H19b H 0.41576(9) 0.34818(15) 0.61959(8) 0.0623(5) Uiso 1.000000 R
C2 C 0.73212(10) 0.43038(19) 0.33431(8) 0.0592(5) Uani 1.000000 .
H2 H 0.77624(10) 0.47528(19) 0.31587(8) 0.0711(5) Uiso 1.000000 R
C12 C 0.65349(11) 0.80513(16) 0.67473(8) 0.0577(4) Uani 1.000000 .
H12 H 0.64687(11) 0.86168(16) 0.71230(8) 0.0693(5) Uiso 1.000000 R
C11 C 0.70908(10) 0.83803(17) 0.62522(8) 0.0576(4) Uani 1.000000 .
H11 H 0.74068(10) 0.91524(17) 0.62978(8) 0.0691(5) Uiso 1.000000 R
C4 C 0.62724(10) 0.26558(17) 0.32472(8) 0.0573(4) Uani 1.000000 .
H4 H 0.60161(10) 0.19992(17) 0.29852(8) 0.0687(5) Uiso 1.000000 R
C3 C 0.69380(10) 0.33203(19) 0.29807(8) 0.0644(5) Uani 1.000000 .
H3 H 0.71248(10) 0.30900(19) 0.25483(8) 0.0773(6) Uiso 1.000000 R
C21 C 0.57061(11) 0.13680(17) 0.63566(8) 0.0659(5) Uani 1.000000 .
H21a H 0.5934(4) 0.0674(8) 0.6073(2) 0.0988(8) Uiso 1.000000 GR
H21b H 0.6108(3) 0.2038(3) 0.6456(5) 0.0988(8) Uiso 1.000000 GR
H21c H 0.55182(16) 0.0974(10) 0.6776(3) 0.0988(8) Uiso 1.000000 GR
C22 C 0.43791(11) 0.09651(18) 0.57936(10) 0.0768(6) Uani 1.000000 .
H22a H 0.3930(4) 0.1397(2) 0.5575(6) 0.1152(9) Uiso 1.000000 GR
H22b H 0.4615(2) 0.0319(7) 0.5487(5) 0.1152(9) Uiso 1.000000 GR
H22c H 0.4198(6) 0.0510(9) 0.61987(12) 0.1152(9) Uiso 1.000000 GR


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
N1 C7 1.4082(16) . ?
N1 C16 1.3946(16) . ?
N1 C6 1.4149(16) . ?
O1 C20 1.2149(17) . ?
C7 C9 1.4339(18) . ?
C7 C8 1.3614(19) . ?
C16 C15 1.3668(18) . ?
C16 C17 1.4958(18) . ?
C14 C9 1.4057(18) . ?
C14 C15 1.4677(19) . ?
C14 C13 1.4001(18) . ?
C6 C1 1.4074(19) . ?
C6 C5 1.3942(19) . ?
C9 C10 1.3991(19) . ?
C15 C20 1.4845(19) . ?
C17 H17a 0.9700 . ?
C17 H17b 0.9700 . ?
C17 C18 1.5277(18) . ?
C1 C8 1.420(2) . ?
C1 C2 1.399(2) . ?
C20 C19 1.496(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(2) . ?
C18 C19 1.516(2) . ?
C18 C21 1.522(2) . ?
C18 C22 1.526(2) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.374(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(2) . ?
C19 H19a 0.9700 . ?
C19 H19b 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.361(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.378(2) . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.388(2) . ?
C3 H3 0.9300 . ?
C21 H21a 0.9600 . ?
C21 H21b 0.9600 . ?
C21 H21c 0.9600 . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 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
C16 N1 C7 121.46(11) . . ?
C6 N1 C7 107.79(10) . . ?
C6 N1 C16 130.30(11) . . ?
C9 C7 N1 118.91(12) . . ?
C8 C7 N1 109.30(12) . . ?
C8 C7 C9 131.73(13) . . ?
C15 C16 N1 119.63(12) . . ?
C17 C16 N1 116.55(11) . . ?
C17 C16 C15 123.77(12) . . ?
C15 C14 C9 118.27(12) . . ?
C13 C14 C9 117.66(13) . . ?
C13 C14 C15 124.06(13) . . ?
C1 C6 N1 106.61(12) . . ?
C5 C6 N1 132.64(13) . . ?
C5 C6 C1 120.60(13) . . ?
C14 C9 C7 119.65(12) . . ?
C10 C9 C7 120.41(13) . . ?
C10 C9 C14 119.91(13) . . ?
C14 C15 C16 121.00(12) . . ?
C20 C15 C16 117.69(12) . . ?
C20 C15 C14 121.25(12) . . ?
H17a C17 C16 108.47(7) . . ?
H17b C17 C16 108.47(7) . . ?
H17b C17 H17a 107.5 . . ?
C18 C17 C16 115.23(12) . . ?
C18 C17 H17a 108.47(8) . . ?
C18 C17 H17b 108.47(7) . . ?
C8 C1 C6 108.34(12) . . ?
C2 C1 C6 119.70(15) . . ?
C2 C1 C8 131.88(15) . . ?
C15 C20 O1 122.36(14) . . ?
C19 C20 O1 120.21(13) . . ?
C19 C20 C15 117.41(12) . . ?
H5 C5 C6 121.05(8) . . ?
C4 C5 C6 117.91(14) . . ?
C4 C5 H5 121.05(10) . . ?
C19 C18 C17 107.40(11) . . ?
C21 C18 C17 109.88(12) . . ?
C21 C18 C19 110.38(13) . . ?
C22 C18 C17 109.48(13) . . ?
C22 C18 C19 109.57(13) . . ?
C22 C18 C21 110.08(13) . . ?
C1 C8 C7 107.87(13) . . ?
H8 C8 C7 126.06(9) . . ?
H8 C8 C1 126.06(8) . . ?
H13 C13 C14 119.38(9) . . ?
C12 C13 C14 121.23(14) . . ?
C12 C13 H13 119.38(9) . . ?
H10 C10 C9 119.51(9) . . ?
C11 C10 C9 120.97(15) . . ?
C11 C10 H10 119.51(10) . . ?
C18 C19 C20 112.13(12) . . ?
H19a C19 C20 109.18(8) . . ?
H19a C19 C18 109.18(8) . . ?
H19b C19 C20 109.18(8) . . ?
H19b C19 C18 109.18(8) . . ?
H19b C19 H19a 107.9 . . ?
H2 C2 C1 120.45(10) . . ?
C3 C2 C1 119.11(16) . . ?
C3 C2 H2 120.45(10) . . ?
H12 C12 C13 119.62(9) . . ?
C11 C12 C13 120.77(15) . . ?
C11 C12 H12 119.62(9) . . ?
C12 C11 C10 119.43(15) . . ?
H11 C11 C10 120.28(10) . . ?
H11 C11 C12 120.28(9) . . ?
H4 C4 C5 119.17(10) . . ?
C3 C4 C5 121.66(15) . . ?
C3 C4 H4 119.17(10) . . ?
C4 C3 C2 120.95(15) . . ?
H3 C3 C2 119.52(10) . . ?
H3 C3 C4 119.52(10) . . ?
H21a C21 C18 109.5 . . ?
H21b C21 C18 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C18 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
H22a C22 C18 109.5 . . ?
H22b C22 C18 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C18 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?

loop_
_atom_type.symbol
_atom_type.scat_dispersion_real
_atom_type.scat_dispersion_imag
_atom_type.scat_Cromer_Mann_a1
_atom_type.scat_Cromer_Mann_a2
_atom_type.scat_Cromer_Mann_a3
_atom_type.scat_Cromer_Mann_a4
_atom_type.scat_Cromer_Mann_b1
_atom_type.scat_Cromer_Mann_b2
_atom_type.scat_Cromer_Mann_b3
_atom_type.scat_Cromer_Mann_b4
_atom_type.scat_Cromer_Mann_c
_atom_type.scat_source
_atom_type.scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 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 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exter014_0m
_database_code_depnum_ccdc_archive 'CCDC 2156735'
loop_
_audit_author_name
_audit_author_address
'VINAYKUMAR KANCHUPALLI'
;Inspire Faculty
India
;
_audit_update_record             
;
2022-03-07 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_chemical_absolute_configuration ?
_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.1663(15)
_cell_length_b                   20.190(7)
_cell_length_c                   14.945(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.836(13)
_cell_angle_gamma                90
_cell_volume                     1547.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1274 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.8625. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19188
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.440
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2601
_reflns_number_total             2695
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.712
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.213
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0937
_refine_ls_restrained_S_all      1.285
_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)+(0.1386P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C17(H17), C4(H4), C5(H5), C19(H19), C20(H20), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 -0.0979(6) 0.64905(14) 0.4754(2) 0.0613(8) Uani 1 1 d . . . . .
N1 N 0.8348(6) 0.45394(16) 0.6441(2) 0.0486(8) Uani 1 1 d . . . . .
H1 H 0.867270 0.486223 0.681294 0.058 Uiso 1 1 calc R . . . .
O2 O -0.0435(8) 0.45780(18) 0.2985(2) 0.0785(11) Uani 1 1 d . . . . .
C17 C 0.0800(7) 0.54110(19) 0.4460(3) 0.0448(9) Uani 1 1 d . . . . .
H17 H -0.044912 0.534480 0.396641 0.054 Uiso 1 1 calc R . . . .
C7 C 0.6458(6) 0.39258(18) 0.5283(2) 0.0398(8) Uani 1 1 d . . . . .
C9 C 0.4538(7) 0.50319(18) 0.5475(2) 0.0407(8) Uani 1 1 d . . . . .
C11 C 0.2828(7) 0.42949(18) 0.4206(2) 0.0400(8) Uani 1 1 d . . . . .
C13 C 0.4846(9) 0.3159(2) 0.4029(3) 0.0488(9) Uani 1 1 d . . . . .
H13A H 0.391301 0.282424 0.432876 0.059 Uiso 1 1 calc R . . . .
H13B H 0.666164 0.302587 0.407287 0.059 Uiso 1 1 calc R . . . .
C4 C 1.1819(9) 0.2722(2) 0.6248(3) 0.0598(11) Uani 1 1 d . . . . .
H4 H 1.255042 0.230675 0.618227 0.072 Uiso 1 1 calc R . . . .
C5 C 0.9652(8) 0.29143(19) 0.5665(3) 0.0511(9) Uani 1 1 d . . . . .
H5 H 0.891849 0.262606 0.522015 0.061 Uiso 1 1 calc R . . . .
C14 C 0.3740(10) 0.3188(2) 0.3042(3) 0.0590(11) Uani 1 1 d . . . . .
H14A H 0.486557 0.345532 0.271156 0.071 Uiso 1 1 calc R . . . .
H14B H 0.365931 0.274589 0.278782 0.071 Uiso 1 1 calc R . . . .
C15 C 0.1068(9) 0.3484(2) 0.2957(3) 0.0602(11) Uani 1 1 d . . . . .
H15A H -0.007175 0.319762 0.325381 0.072 Uiso 1 1 calc R . . . .
H15B H 0.038688 0.350784 0.232383 0.072 Uiso 1 1 calc R . . . .
C10 C 0.2698(6) 0.49159(19) 0.4701(2) 0.0400(8) Uani 1 1 d . . . . .
C12 C 0.4654(7) 0.38132(17) 0.4505(2) 0.0389(8) Uani 1 1 d . . . . .
C19 C 0.2646(8) 0.6106(2) 0.5695(3) 0.0526(10) Uani 1 1 d . . . . .
H19 H 0.264127 0.650356 0.600853 0.063 Uiso 1 1 calc R . . . .
C18 C 0.0783(8) 0.59899(19) 0.4949(3) 0.0472(9) Uani 1 1 d . . . . .
C16 C 0.1045(8) 0.41713(19) 0.3364(3) 0.0468(9) Uani 1 1 d . . . . .
C8 C 0.6407(7) 0.45319(17) 0.5744(2) 0.0413(8) Uani 1 1 d . . . . .
C6 C 0.8575(7) 0.35474(18) 0.5753(3) 0.0427(8) Uani 1 1 d . . . . .
C20 C 0.4470(8) 0.5632(2) 0.5958(3) 0.0510(10) Uani 1 1 d . . . . .
H20 H 0.567820 0.570492 0.646075 0.061 Uiso 1 1 calc R . . . .
C3 C 1.2915(9) 0.3145(3) 0.6930(3) 0.0614(11) Uani 1 1 d . . . . .
H3 H 1.437079 0.300594 0.731050 0.074 Uiso 1 1 calc R . . . .
C21 C -0.2933(10) 0.6398(2) 0.4009(3) 0.0622(11) Uani 1 1 d . . . . .
H21A H -0.212413 0.635279 0.346669 0.093 Uiso 1 1 calc GR . . . .
H21B H -0.407837 0.677449 0.395712 0.093 Uiso 1 1 calc GR . . . .
H21C H -0.391566 0.600591 0.410193 0.093 Uiso 1 1 calc GR . . . .
C2 C 1.1894(9) 0.3756(2) 0.7051(3) 0.0576(10) Uani 1 1 d . . . . .
H2 H 1.262260 0.403391 0.750926 0.069 Uiso 1 1 calc R . . . .
C1 C 0.9720(7) 0.3954(2) 0.6465(3) 0.0458(8) 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
O1 C18 1.368(5) . ?
O1 C21 1.422(7) . ?
N1 C8 1.357(5) . ?
N1 C1 1.377(5) . ?
O2 C16 1.215(5) . ?
C17 C10 1.416(5) . ?
C17 C18 1.379(5) . ?
C7 C12 1.418(5) . ?
C7 C8 1.406(5) . ?
C7 C6 1.446(5) . ?
C9 C10 1.427(5) . ?
C9 C8 1.422(5) . ?
C9 C20 1.412(5) . ?
C11 C10 1.461(5) . ?
C11 C12 1.391(5) . ?
C11 C16 1.489(5) . ?
C13 C14 1.517(6) . ?
C13 C12 1.510(5) . ?
C4 C5 1.389(6) . ?
C4 C3 1.397(7) . ?
C5 C6 1.407(5) . ?
C14 C15 1.496(7) . ?
C15 C16 1.516(6) . ?
C19 C18 1.403(6) . ?
C19 C20 1.368(6) . ?
C6 C1 1.416(6) . ?
C3 C2 1.363(7) . ?
C2 C1 1.397(6) . ?

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
C18 O1 C21 117.5(3) . . ?
C8 N1 C1 110.0(3) . . ?
C18 C17 C10 120.8(4) . . ?
C12 C7 C6 134.3(3) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 C6 106.2(3) . . ?
C8 C9 C10 118.5(3) . . ?
C20 C9 C10 120.0(3) . . ?
C20 C9 C8 121.4(4) . . ?
C10 C11 C16 120.7(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C13 C14 112.6(3) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 119.6(4) . . ?
C15 C14 C13 109.6(4) . . ?
C14 C15 C16 112.5(4) . . ?
C17 C10 C9 117.7(3) . . ?
C17 C10 C11 123.3(3) . . ?
C9 C10 C11 119.0(3) . . ?
C7 C12 C13 116.9(3) . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 C13 122.7(3) . . ?
C20 C19 C18 119.7(4) . . ?
O1 C18 C17 124.0(4) . . ?
O1 C18 C19 115.0(3) . . ?
C17 C18 C19 121.0(4) . . ?
O2 C16 C11 124.9(4) . . ?
O2 C16 C15 117.7(4) . . ?
C11 C16 C15 117.3(4) . . ?
N1 C8 C7 109.3(3) . . ?
N1 C8 C9 128.6(3) . . ?
C7 C8 C9 122.1(4) . . ?
C5 C6 C7 136.0(4) . . ?
C5 C6 C1 117.5(4) . . ?
C1 C6 C7 106.5(3) . . ?
C19 C20 C9 120.8(4) . . ?
C2 C3 C4 121.3(4) . . ?
C3 C2 C1 118.1(5) . . ?
N1 C1 C6 108.1(3) . . ?
N1 C1 C2 129.4(4) . . ?
C2 C1 C6 122.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
