# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1482717'

_audit_update_record             
;
2016-05-31 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
# publcif _publ_body_element loop end
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            
2-(3-benzoyl-6-chloro-2-phenyl-1,4-dihydro-4-quinolinyl)acetaldehyde
_chemical_name_systematic        
2-(3-benzoyl-6-chloro-2-phenyl-1,4-dihydro-4-quinolinyl)acetaldehyde
_chemical_formula_moiety         'C24 H18 Cl N O2'
_chemical_formula_sum            'C24 H18 Cl N O2'
_chemical_formula_weight         387.84
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9587(3)
_cell_length_b                   7.7456(2)
_cell_length_c                   22.4121(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.1510(10)
_cell_angle_gamma                90.00
_cell_volume                     1872.60(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    267
_cell_measurement_temperature    296.15(2)
_cell_measurement_theta_max      26.7
_cell_measurement_theta_min      2.3
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lustrous,light,needle
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.103
_exptl_special_details           ?
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            66778
_diffrn_reflns_theta_full        26.07
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_temperature      296.15.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  None
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_reflns_number_gt                2619
_reflns_number_total             3714
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0089(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3714
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.6845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.43853(6) -0.01146(9) 0.23827(3) 0.0568(2) Uani 1 d . . .
N1 N -0.03037(17) -0.0231(2) 0.09961(9) 0.0403(5) Uani 1 d . . .
H1 H -0.0084 -0.1191 0.0834 0.048 Uiso 1 calc . . R
O2 O 0.01650(15) 0.5793(2) 0.09638(8) 0.0524(5) Uani 1 d . . .
O0AA O -0.3891(2) 0.4538(3) 0.07371(12) 0.0845(7) Uani 1 d . . .
C1 C -0.2736(2) -0.1720(3) 0.18127(11) 0.0447(6) Uani 1 d . . .
H1A H -0.3040 -0.2763 0.1955 0.054 Uiso 1 calc . . R
C2 C -0.1780(2) -0.1752(3) 0.14875(11) 0.0443(6) Uani 1 d . . .
H2 H -0.1417 -0.2822 0.1407 0.053 Uiso 1 calc . . R
C3 C -0.13472(19) -0.0228(3) 0.12767(10) 0.0361(5) Uani 1 d . . .
C4 C 0.03799(19) 0.1238(3) 0.09708(10) 0.0355(5) Uani 1 d . . .
C5 C -0.01129(19) 0.2811(3) 0.10705(10) 0.0357(5) Uani 1 d . . .
C6 C 0.0618(2) 0.4395(3) 0.11484(10) 0.0371(5) Uani 1 d . . .
C7 C 0.1909(2) 0.4354(3) 0.15073(10) 0.0365(5) Uani 1 d . . .
C8 C 0.2206(2) 0.3344(3) 0.20230(11) 0.0453(6) Uani 1 d . . .
H8 H 0.1595 0.2616 0.2144 0.054 Uiso 1 calc . . R
C9 C 0.3392(3) 0.3393(4) 0.23638(12) 0.0572(7) Uani 1 d . . .
H9 H 0.3585 0.2721 0.2723 0.069 Uiso 1 calc . . R
C10 C 0.4287(3) 0.4408(4) 0.21849(13) 0.0635(8) Uani 1 d . . .
H10 H 0.5102 0.4421 0.2415 0.076 Uiso 1 calc . . R
C11 C 0.1614(2) 0.1005(3) 0.07975(10) 0.0359(5) Uani 1 d . . .
C12 C 0.2487(2) -0.0094(3) 0.11146(11) 0.0462(6) Uani 1 d . . .
H12 H 0.2281 -0.0773 0.1436 0.055 Uiso 1 calc . . R
C13 C 0.3655(2) -0.0213(4) 0.09684(13) 0.0585(7) Uani 1 d . . .
H13 H 0.4250 -0.0968 0.1192 0.070 Uiso 1 calc . . R
C14 C 0.3962(3) 0.0733(4) 0.05103(15) 0.0670(9) Uani 1 d . . .
H14 H 0.4777 0.0666 0.0421 0.080 Uiso 1 calc . . R
C15 C 0.3100(3) 0.1788(4) 0.01741(14) 0.0669(9) Uani 1 d . . .
H15 H 0.3309 0.2423 -0.0156 0.080 Uiso 1 calc . . R
C16 C 0.1919(3) 0.1932(3) 0.03161(11) 0.0506(6) Uani 1 d . . .
H16 H 0.1322 0.2665 0.0083 0.061 Uiso 1 calc . . R
C17 C -0.14955(19) 0.2938(3) 0.10591(10) 0.0365(5) Uani 1 d . . .
H17 H -0.1662 0.3977 0.1297 0.044 Uiso 1 calc . . R
C18 C -0.19179(19) 0.1349(3) 0.13583(10) 0.0348(5) Uani 1 d . . .
C19 C -0.2866(2) 0.1369(3) 0.16974(10) 0.0389(5) Uani 1 d . . .
H19 H -0.3253 0.2429 0.1769 0.047 Uiso 1 calc . . R
C20 C -0.3244(2) -0.0152(3) 0.19296(10) 0.0407(5) Uani 1 d . . .
C21 C -0.2193(2) 0.3141(3) 0.04044(11) 0.0457(6) Uani 1 d . . .
H21A H -0.1706 0.3911 0.0184 0.055 Uiso 1 calc . . R
H21B H -0.2238 0.1997 0.0204 0.055 Uiso 1 calc . . R
C22 C -0.3466(3) 0.3842(4) 0.03452(15) 0.0621(8) Uani 1 d . . .
H22 H -0.3990 0.3728 -0.0038 0.075 Uiso 1 calc . . R
C23 C 0.4005(2) 0.5401(4) 0.16743(14) 0.0638(8) Uani 1 d . . .
H23 H 0.4628 0.6094 0.1548 0.077 Uiso 1 calc . . R
C24 C 0.2819(2) 0.5398(3) 0.13419(11) 0.0470(6) Uani 1 d . . .
H24 H 0.2625 0.6120 0.0996 0.056 Uiso 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
Cl1 C20 1.745(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.399(3) . ?
N1 C4 1.369(3) . ?
O2 C6 1.232(3) . ?
O0AA C22 1.193(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.377(3) . ?
C1 C20 1.380(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 C18 1.399(3) . ?
C4 C5 1.367(3) . ?
C4 C11 1.482(3) . ?
C5 C6 1.459(3) . ?
C5 C17 1.514(3) . ?
C6 C7 1.499(3) . ?
C7 C8 1.386(3) . ?
C7 C24 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.371(4) . ?
C10 H10 0.9500 . ?
C10 C23 1.368(4) . ?
C11 C12 1.380(3) . ?
C11 C16 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.351(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(4) . ?
C16 H16 0.9500 . ?
C17 H17 1.0000 . ?
C17 C18 1.513(3) . ?
C17 C21 1.538(3) . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.481(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.379(4) . ?
C24 H24 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
C3 N1 H1 119.5 . . ?
C4 N1 H1 119.5 . . ?
C4 N1 C3 120.94(18) . . ?
C2 C1 H1A 120.5 . . ?
C2 C1 C20 119.1(2) . . ?
C20 C1 H1A 120.5 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 N1 120.54(19) . . ?
C2 C3 C18 120.7(2) . . ?
C18 C3 N1 118.68(19) . . ?
N1 C4 C11 116.17(18) . . ?
C5 C4 N1 119.94(19) . . ?
C5 C4 C11 123.79(19) . . ?
C4 C5 C6 123.00(19) . . ?
C4 C5 C17 118.56(19) . . ?
C6 C5 C17 118.32(18) . . ?
O2 C6 C5 121.2(2) . . ?
O2 C6 C7 119.0(2) . . ?
C5 C6 C7 119.52(19) . . ?
C8 C7 C6 121.3(2) . . ?
C24 C7 C6 120.0(2) . . ?
C24 C7 C8 118.6(2) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C23 C10 C9 119.9(3) . . ?
C23 C10 H10 120.0 . . ?
C12 C11 C4 121.4(2) . . ?
C12 C11 C16 118.7(2) . . ?
C16 C11 C4 119.9(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.9(3) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C5 C17 H17 108.6 . . ?
C5 C17 C21 110.52(18) . . ?
C18 C17 C5 108.85(17) . . ?
C18 C17 H17 108.6 . . ?
C18 C17 C21 111.49(18) . . ?
C21 C17 H17 108.6 . . ?
C3 C18 C17 118.28(19) . . ?
C19 C18 C3 118.4(2) . . ?
C19 C18 C17 123.30(19) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C1 C20 Cl1 118.70(18) . . ?
C1 C20 C19 121.4(2) . . ?
C19 C20 Cl1 119.90(18) . . ?
C17 C21 H21A 108.5 . . ?
C17 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 C17 115.2(2) . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
O0AA C22 C21 125.7(3) . . ?
O0AA C22 H22 117.2 . . ?
C21 C22 H22 117.2 . . ?
C10 C23 H23 119.9 . . ?
C10 C23 C24 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C7 C24 H24 119.6 . . ?
C23 C24 C7 120.7(2) . . ?
C23 C24 H24 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C18 C17 8.7(3) . . . . ?
N1 C3 C18 C19 -172.84(19) . . . . ?
N1 C4 C5 C6 169.8(2) . . . . ?
N1 C4 C5 C17 -14.3(3) . . . . ?
N1 C4 C11 C12 -55.9(3) . . . . ?
N1 C4 C11 C16 125.6(2) . . . . ?
O2 C6 C7 C8 136.9(2) . . . . ?
O2 C6 C7 C24 -40.1(3) . . . . ?
C1 C2 C3 N1 174.0(2) . . . . ?
C1 C2 C3 C18 -3.9(3) . . . . ?
C2 C1 C20 Cl1 -175.96(18) . . . . ?
C2 C1 C20 C19 3.9(4) . . . . ?
C2 C3 C18 C17 -173.4(2) . . . . ?
C2 C3 C18 C19 5.0(3) . . . . ?
C3 N1 C4 C5 -17.4(3) . . . . ?
C3 N1 C4 C11 166.05(19) . . . . ?
C3 C18 C19 C20 -1.8(3) . . . . ?
C4 N1 C3 C2 -157.7(2) . . . . ?
C4 N1 C3 C18 20.2(3) . . . . ?
C4 C5 C6 O2 145.9(2) . . . . ?
C4 C5 C6 C7 -39.6(3) . . . . ?
C4 C5 C17 C18 38.9(3) . . . . ?
C4 C5 C17 C21 -83.9(2) . . . . ?
C4 C11 C12 C13 -176.1(2) . . . . ?
C4 C11 C16 C15 176.4(2) . . . . ?
C5 C4 C11 C12 127.7(2) . . . . ?
C5 C4 C11 C16 -50.8(3) . . . . ?
C5 C6 C7 C8 -37.8(3) . . . . ?
C5 C6 C7 C24 145.3(2) . . . . ?
C5 C17 C18 C3 -35.7(3) . . . . ?
C5 C17 C18 C19 146.0(2) . . . . ?
C5 C17 C21 C22 -160.8(2) . . . . ?
C6 C5 C17 C18 -145.00(19) . . . . ?
C6 C5 C17 C21 92.2(2) . . . . ?
C6 C7 C8 C9 -176.8(2) . . . . ?
C6 C7 C24 C23 178.7(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C7 C24 C23 1.7(4) . . . . ?
C8 C9 C10 C23 1.2(4) . . . . ?
C9 C10 C23 C24 0.6(5) . . . . ?
C10 C23 C24 C7 -2.1(4) . . . . ?
C11 C4 C5 C6 -13.9(3) . . . . ?
C11 C4 C5 C17 161.9(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C11 C16 C15 -2.1(3) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 2.1(4) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C16 C11 C12 C13 2.4(3) . . . . ?
C17 C5 C6 O2 -30.0(3) . . . . ?
C17 C5 C6 C7 144.5(2) . . . . ?
C17 C18 C19 C20 176.5(2) . . . . ?
C17 C21 C22 O0AA 14.7(4) . . . . ?
C18 C17 C21 C22 78.0(3) . . . . ?
C18 C19 C20 Cl1 177.18(16) . . . . ?
C18 C19 C20 C1 -2.7(3) . . . . ?
C20 C1 C2 C3 -0.6(4) . . . . ?
C21 C17 C18 C3 86.5(2) . . . . ?
C21 C17 C18 C19 -91.9(2) . . . . ?
C24 C7 C8 C9 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_q
_database_code_depnum_ccdc_archive 'CCDC 1838494'
_audit_update_record             
;
2018-04-20 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_audit_creation_date             2018-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
((5-(Methylthio)-2-phenylquinolin-3-yl)(thiophen-2-yl)methanone
_chemical_formula_moiety         'C21 H15 N O2 S'
_chemical_formula_sum            'C21 H15 N O2 S'
_chemical_formula_weight         345.40
_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'
S S 0.1246 0.1234 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.0386(7)
_cell_length_b                   16.6863(11)
_cell_length_c                   10.3764(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1738.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    422
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0949 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.8283.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.793
_exptl_crystal_size_mid          0.562
_exptl_crystal_size_min          0.508
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27881
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.124
_diffrn_reflns_theta_min         2.311
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker  D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3060
_reflns_number_total             3426
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.093
_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)+(0.0361P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0718
_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 Aromatic/amide H refined with riding coordinates:
 C21(H21), C19(H19), C8(H8), C15(H15), C14(H14), C13(H13), C20(H20), C16(H16),
 C12(H12), C3(H3), C2(H2), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S1 S -0.66580(7) 0.17297(3) -0.52660(7) 0.0514(2) Uani 1 1 d . . . . .
O2 O -0.55226(19) 0.07794(9) -0.74471(17) 0.0517(5) Uani 1 1 d . . . . .
O1 O -0.2280(2) -0.31683(11) -0.4017(2) 0.0549(5) Uani 1 1 d . . . . .
C4 C -0.3144(2) -0.27722(14) -0.4818(3) 0.0413(6) Uani 1 1 d . . . . .
C21 C -0.7389(3) 0.16422(17) -0.3789(3) 0.0546(7) Uani 1 1 d . . . . .
H21 H -0.7720 0.2074 -0.3320 0.065 Uiso 1 1 calc R . . . .
C6 C -0.4333(2) -0.16357(12) -0.5645(2) 0.0323(5) Uani 1 1 d . . . . .
C19 C -0.6872(2) 0.03339(14) -0.4266(2) 0.0395(6) Uani 1 1 d . . . . .
H19 H -0.6821 -0.0216 -0.4128 0.047 Uiso 1 1 calc R . . . .
C1 C -0.4955(2) -0.21184(12) -0.6589(2) 0.0349(5) Uani 1 1 d . . . . .
C8 C -0.4684(2) -0.08181(12) -0.5629(2) 0.0344(5) Uani 1 1 d . . . . .
H8 H -0.4317 -0.0480 -0.5011 0.041 Uiso 1 1 calc R . . . .
C11 C -0.7128(2) -0.07828(13) -0.8421(2) 0.0370(5) Uani 1 1 d . . . . .
C10 C -0.6138(2) -0.10486(12) -0.7446(2) 0.0325(5) Uani 1 1 d . . . . .
N1 N -0.58367(18) -0.18221(11) -0.7467(2) 0.0373(4) Uani 1 1 d . . . . .
C9 C -0.5563(2) -0.05179(12) -0.6517(2) 0.0321(5) Uani 1 1 d . . . . .
C17 C -0.5815(2) 0.03668(12) -0.6516(2) 0.0345(5) Uani 1 1 d . . . . .
C18 C -0.6410(2) 0.07067(12) -0.5359(2) 0.0361(5) Uani 1 1 d . . . . .
C15 C -0.8060(3) -0.0911(2) -1.0561(3) 0.0687(9) Uani 1 1 d . . . . .
H15 H -0.8045 -0.1146 -1.1373 0.082 Uiso 1 1 calc R . . . .
C14 C -0.9012(3) -0.0339(2) -1.0272(4) 0.0737(9) Uani 1 1 d . . . . .
H14 H -0.9633 -0.0186 -1.0890 0.088 Uiso 1 1 calc R . . . .
C13 C -0.9037(3) 0.00050(18) -0.9064(3) 0.0624(8) Uani 1 1 d . . . . .
H13 H -0.9686 0.0383 -0.8864 0.075 Uiso 1 1 calc R . . . .
C7 C -0.1490(3) -0.26884(18) -0.3180(3) 0.0589(8) Uani 1 1 d . . . . .
H7A H -0.1014 -0.2296 -0.3677 0.088 Uiso 1 1 calc GR . . . .
H7B H -0.0866 -0.3023 -0.2730 0.088 Uiso 1 1 calc GR . . . .
H7C H -0.2055 -0.2422 -0.2569 0.088 Uiso 1 1 calc GR . . . .
C20 C -0.7433(3) 0.08763(15) -0.3377(3) 0.0485(6) Uani 1 1 d . . . . .
H20 H -0.7796 0.0722 -0.2590 0.058 Uiso 1 1 calc R . . . .
C16 C -0.7131(3) -0.11327(15) -0.9647(3) 0.0484(6) Uani 1 1 d . . . . .
H16 H -0.6499 -0.1520 -0.9849 0.058 Uiso 1 1 calc R . . . .
C12 C -0.8104(2) -0.02100(15) -0.8151(3) 0.0454(6) Uani 1 1 d . . . . .
H12 H -0.8124 0.0030 -0.7342 0.054 Uiso 1 1 calc R . . . .
C3 C -0.3788(3) -0.32594(13) -0.5734(3) 0.0462(6) Uani 1 1 d . . . . .
H3 H -0.3615 -0.3807 -0.5743 0.055 Uiso 1 1 calc R . . . .
C2 C -0.4653(2) -0.29509(14) -0.6601(3) 0.0455(6) Uani 1 1 d . . . . .
H2 H -0.5051 -0.3284 -0.7207 0.055 Uiso 1 1 calc R . . . .
C5 C -0.3401(2) -0.19693(14) -0.4773(2) 0.0386(5) Uani 1 1 d . . . . .
H5 H -0.2969 -0.1645 -0.4175 0.046 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
S1 C21 1.706(3) . ?
S1 C18 1.728(2) . ?
O2 C17 1.223(3) . ?
O1 C4 1.371(3) . ?
O1 C7 1.423(4) . ?
C4 C3 1.408(4) . ?
C4 C5 1.365(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.348(4) . ?
C6 C1 1.413(3) . ?
C6 C8 1.409(3) . ?
C6 C5 1.416(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.374(3) . ?
C19 C20 1.410(3) . ?
C1 N1 1.363(3) . ?
C1 C2 1.422(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(3) . ?
C11 C10 1.486(3) . ?
C11 C16 1.400(4) . ?
C11 C12 1.397(3) . ?
C10 N1 1.326(3) . ?
C10 C9 1.431(3) . ?
C9 C17 1.498(3) . ?
C17 C18 1.456(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(5) . ?
C15 C16 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.378(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.352(4) . ?
C2 H2 0.9300 . ?
C5 H5 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 S1 C18 91.57(13) . . ?
C4 O1 C7 116.83(19) . . ?
O1 C4 C3 114.9(2) . . ?
C5 C4 O1 124.9(2) . . ?
C5 C4 C3 120.2(2) . . ?
S1 C21 H21 123.8 . . ?
C20 C21 S1 112.4(2) . . ?
C20 C21 H21 123.8 . . ?
C1 C6 C5 120.71(19) . . ?
C8 C6 C1 116.7(2) . . ?
C8 C6 C5 122.6(2) . . ?
C18 C19 H19 123.7 . . ?
C18 C19 C20 112.6(2) . . ?
C20 C19 H19 123.7 . . ?
C6 C1 C2 118.0(2) . . ?
N1 C1 C6 122.89(19) . . ?
N1 C1 C2 119.1(2) . . ?
C6 C8 H8 119.8 . . ?
C9 C8 C6 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C16 C11 C10 119.7(2) . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 C16 117.8(2) . . ?
N1 C10 C11 115.6(2) . . ?
N1 C10 C9 121.4(2) . . ?
C9 C10 C11 122.95(19) . . ?
C10 N1 C1 119.37(19) . . ?
C8 C9 C10 119.11(19) . . ?
C8 C9 C17 117.95(19) . . ?
C10 C9 C17 122.8(2) . . ?
O2 C17 C9 120.9(2) . . ?
O2 C17 C18 122.08(19) . . ?
C18 C17 C9 116.99(18) . . ?
C19 C18 S1 110.64(18) . . ?
C19 C18 C17 130.00(19) . . ?
C17 C18 S1 119.33(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C21 C20 C19 112.8(3) . . ?
C21 C20 H20 123.6 . . ?
C19 C20 H20 123.6 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeCN'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1482718'
#Added by publCIF



_audit_update_record             
;
2016-05-31 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
#Added by publCIF




_diffrn_radiation_monochromator  None
# publcif _publ_body_element loop end
_audit_creation_date             2016-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        2-furyl(2-phenyl-3-quinolinyl)methanone
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31
_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                   12.1150(9)
_cell_length_b                   16.3598(14)
_cell_length_c                   7.7826(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.183(3)
_cell_angle_gamma                90
_cell_volume                     1465.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    391
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0827 after correction.
The Ratio of minimum to maximum transmission is 0.8479.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.07
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            46541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.163
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 0.77
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2950
_reflns_number_total             3373
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0112(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.061
_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)+(0.0427P)²+0.9182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.83352(8) 1.06481(5) 0.03284(12) 0.0167(2) Uani 1 1 d . . . . .
O2 O 0.68812(9) 1.01810(6) 0.22747(14) 0.0224(2) Uani 1 1 d . . . . .
N1 N 0.70274(9) 0.73522(7) 0.15105(15) 0.0166(2) Uani 1 1 d . . . . .
C1 C 0.87174(12) 1.00023(9) -0.19570(18) 0.0206(3) Uani 1 1 d . . . . .
H1 H 0.8995 0.9895 -0.2949 0.025 Uiso 1 1 calc R . . . .
C2 C 0.80731(11) 0.94614(8) -0.12116(17) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.7841 0.8919 -0.1596 0.021 Uiso 1 1 calc R . . . .
C3 C 0.78540(11) 0.98757(7) 0.01673(17) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.71542(11) 0.96736(8) 0.13274(17) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.67106(11) 0.88080(8) 0.11580(17) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.74276(11) 0.81092(7) 0.18284(16) 0.0135(3) Uani 1 1 d . . . . .
C7 C 0.86731(10) 0.81897(7) 0.29261(16) 0.0130(2) Uani 1 1 d . . . . .
C8 C 0.90744(11) 0.88411(7) 0.41212(16) 0.0145(3) Uani 1 1 d . . . . .
H8 H 0.8544 0.9246 0.4251 0.017 Uiso 1 1 calc R . . . .
C9 C 1.02445(11) 0.89002(8) 0.51218(17) 0.0161(3) Uani 1 1 d . . . . .
H9 H 1.0508 0.9345 0.5931 0.019 Uiso 1 1 calc R . . . .
C10 C 1.10286(11) 0.83134(8) 0.49455(17) 0.0164(3) Uani 1 1 d . . . . .
H10 H 1.1829 0.8361 0.5614 0.020 Uiso 1 1 calc R . . . .
C11 C 0.88597(12) 1.06984(8) -0.09844(18) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.9272 1.1164 -0.1187 0.023 Uiso 1 1 calc R . . . .
C12 C 0.55624(11) 0.86903(8) 0.02104(18) 0.0180(3) Uani 1 1 d . . . . .
H12 H 0.5068 0.9148 -0.0206 0.022 Uiso 1 1 calc R . . . .
C13 C 0.51131(11) 0.78916(8) -0.01476(17) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.58899(11) 0.72340(8) 0.05105(18) 0.0172(3) Uani 1 1 d . . . . .
C15 C 0.94664(11) 0.75932(8) 0.27845(17) 0.0146(3) Uani 1 1 d . . . . .
H15 H 0.9204 0.7141 0.1997 0.017 Uiso 1 1 calc R . . . .
C16 C 1.06343(11) 0.76552(8) 0.37831(17) 0.0163(3) Uani 1 1 d . . . . .
H16 H 1.1166 0.7247 0.3672 0.020 Uiso 1 1 calc R . . . .
C17 C 0.54787(13) 0.64235(9) 0.0112(2) 0.0266(3) Uani 1 1 d . . . . .
H17 H 0.5989 0.5975 0.0539 0.032 Uiso 1 1 calc R . . . .
C18 C 0.43431(13) 0.62857(9) -0.0889(2) 0.0295(3) Uani 1 1 d . . . . .
H18 H 0.4072 0.5741 -0.1150 0.035 Uiso 1 1 calc R . . . .
C19 C 0.35737(12) 0.69439(10) -0.1536(2) 0.0264(3) Uani 1 1 d . . . . .
H19 H 0.2790 0.6838 -0.2228 0.032 Uiso 1 1 calc R . . . .
C20 C 0.39438(12) 0.77308(9) -0.11759(19) 0.0229(3) Uani 1 1 d . . . . .
H20 H 0.3419 0.8170 -0.1614 0.027 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 C3 1.3810(15) . ?
O1 C11 1.3637(16) . ?
O2 C4 1.2224(16) . ?
N1 C6 1.3248(16) . ?
N1 C14 1.3685(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.4182(19) . ?
C1 C11 1.348(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3635(18) . ?
C3 C4 1.4563(18) . ?
C4 C5 1.5057(17) . ?
C5 C6 1.4321(17) . ?
C5 C12 1.3695(18) . ?
C6 C7 1.4898(17) . ?
C7 C8 1.3982(17) . ?
C7 C15 1.3979(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3915(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3872(18) . ?
C10 H10 0.9500 . ?
C10 C16 1.3915(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.4095(19) . ?
C13 C14 1.4158(19) . ?
C13 C20 1.4174(18) . ?
C14 C17 1.4164(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3893(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.372(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.410(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.363(2) . ?
C20 H20 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
C11 O1 C3 105.63(10) . . ?
C6 N1 C14 118.89(11) . . ?
C2 C1 H1 126.6 . . ?
C11 C1 H1 126.6 . . ?
C11 C1 C2 106.71(12) . . ?
C1 C2 H2 126.9 . . ?
C3 C2 C1 106.20(12) . . ?
C3 C2 H2 126.9 . . ?
O1 C3 C4 117.54(11) . . ?
C2 C3 O1 110.23(11) . . ?
C2 C3 C4 132.00(12) . . ?
O2 C4 C3 122.63(12) . . ?
O2 C4 C5 122.35(12) . . ?
C3 C4 C5 114.85(11) . . ?
C6 C5 C4 124.02(11) . . ?
C12 C5 C4 117.01(11) . . ?
C12 C5 C6 118.85(12) . . ?
N1 C6 C5 122.22(11) . . ?
N1 C6 C7 115.84(11) . . ?
C5 C6 C7 121.94(11) . . ?
C8 C7 C6 121.91(11) . . ?
C15 C7 C6 119.43(11) . . ?
C15 C7 C8 118.66(11) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(12) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.40(12) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C16 119.55(11) . . ?
C16 C10 H10 120.2 . . ?
O1 C11 H11 124.4 . . ?
C1 C11 O1 111.21(12) . . ?
C1 C11 H11 124.4 . . ?
C5 C12 H12 120.0 . . ?
C5 C12 C13 120.10(12) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 117.45(12) . . ?
C12 C13 C20 122.68(12) . . ?
C14 C13 C20 119.84(12) . . ?
N1 C14 C13 122.41(12) . . ?
N1 C14 C17 118.67(12) . . ?
C13 C14 C17 118.92(12) . . ?
C7 C15 H15 119.7 . . ?
C16 C15 C7 120.68(12) . . ?
C16 C15 H15 119.7 . . ?
C10 C16 H16 119.9 . . ?
C15 C16 C10 120.21(12) . . ?
C15 C16 H16 119.9 . . ?
C14 C17 H17 120.0 . . ?
C18 C17 C14 120.00(14) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.76(14) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.61(13) . . ?
C20 C19 H19 119.7 . . ?
C13 C20 H20 120.1 . . ?
C19 C20 C13 119.87(13) . . ?
C19 C20 H20 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 O2 7.99(18) . . . . ?
O1 C3 C4 C5 -176.77(10) . . . . ?
O2 C4 C5 C6 -112.73(15) . . . . ?
O2 C4 C5 C12 71.15(16) . . . . ?
N1 C6 C7 C8 -146.53(12) . . . . ?
N1 C6 C7 C15 32.53(16) . . . . ?
N1 C14 C17 C18 -179.92(14) . . . . ?
C1 C2 C3 O1 -0.33(14) . . . . ?
C1 C2 C3 C4 173.96(13) . . . . ?
C2 C1 C11 O1 -0.85(15) . . . . ?
C2 C3 C4 O2 -165.97(13) . . . . ?
C2 C3 C4 C5 9.3(2) . . . . ?
C3 O1 C11 C1 0.64(14) . . . . ?
C3 C4 C5 C6 72.01(15) . . . . ?
C3 C4 C5 C12 -104.11(13) . . . . ?
C4 C5 C6 N1 -173.72(12) . . . . ?
C4 C5 C6 C7 6.17(18) . . . . ?
C4 C5 C12 C13 174.07(11) . . . . ?
C5 C6 C7 C8 33.57(18) . . . . ?
C5 C6 C7 C15 -147.37(12) . . . . ?
C5 C12 C13 C14 0.15(19) . . . . ?
C5 C12 C13 C20 -177.67(13) . . . . ?
C6 N1 C14 C13 -2.15(19) . . . . ?
C6 N1 C14 C17 177.46(13) . . . . ?
C6 C5 C12 C13 -2.26(19) . . . . ?
C6 C7 C8 C9 -179.74(11) . . . . ?
C6 C7 C15 C16 179.58(11) . . . . ?
C7 C8 C9 C10 0.04(18) . . . . ?
C7 C15 C16 C10 0.23(19) . . . . ?
C8 C7 C15 C16 -1.32(18) . . . . ?
C8 C9 C10 C16 -1.14(18) . . . . ?
C9 C10 C16 C15 1.01(19) . . . . ?
C11 O1 C3 C2 -0.16(13) . . . . ?
C11 O1 C3 C4 -175.38(11) . . . . ?
C11 C1 C2 C3 0.71(15) . . . . ?
C12 C5 C6 N1 2.34(19) . . . . ?
C12 C5 C6 C7 -177.78(12) . . . . ?
C12 C13 C14 N1 2.14(19) . . . . ?
C12 C13 C14 C17 -177.47(13) . . . . ?
C12 C13 C20 C19 177.40(13) . . . . ?
C13 C14 C17 C18 -0.3(2) . . . . ?
C14 N1 C6 C5 -0.12(18) . . . . ?
C14 N1 C6 C7 179.99(11) . . . . ?
C14 C13 C20 C19 -0.4(2) . . . . ?
C14 C17 C18 C19 0.1(2) . . . . ?
C15 C7 C8 C9 1.19(18) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C13 0.2(2) . . . . ?
C20 C13 C14 N1 -179.97(12) . . . . ?
C20 C13 C14 C17 0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

