# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_av_mm89
_database_code_depnum_ccdc_archive 'CCDC 934415'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
6-Nitro-2-phenyl-1-(3-phenylpropyl)quinolin-4(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O3'
_chemical_formula_sum            'C24 H20 N2 O3'
_chemical_formula_weight         384.42

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.4213(5)
_cell_length_b                   15.0974(8)
_cell_length_c                   24.6279(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3874.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6203
_cell_measurement_theta_min      5.121
_cell_measurement_theta_max      57.698

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22580
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5541
_reflns_number_gt                3855
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.6124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5541
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.67231(9) 0.02075(6) 0.56783(4) 0.0244(2) Uani 1 1 d . . .
N2 N 1.01149(12) -0.00639(9) 0.39121(5) 0.0415(3) Uani 1 1 d . . .
O1 O 0.84368(10) 0.24502(6) 0.50777(4) 0.0426(3) Uani 1 1 d . . .
O2 O 1.06710(11) 0.06078(9) 0.37615(4) 0.0583(3) Uani 1 1 d . . .
O3 O 1.02903(12) -0.07983(8) 0.37118(5) 0.0606(3) Uani 1 1 d . . .
C1 C 0.64340(11) 0.10334(7) 0.58861(5) 0.0257(3) Uani 1 1 d . . .
C2 C 0.69702(12) 0.17839(8) 0.56837(5) 0.0303(3) Uani 1 1 d . . .
H2 H 0.6723 0.2337 0.5835 0.036 Uiso 1 1 calc R . .
C3 C 0.78850(12) 0.17790(8) 0.52556(5) 0.0292(3) Uani 1 1 d . . .
C4 C 0.81390(11) 0.09009(7) 0.50267(5) 0.0248(2) Uani 1 1 d . . .
C5 C 0.89918(12) 0.08243(8) 0.45906(5) 0.0290(3) Uani 1 1 d . . .
H5 H 0.9415 0.1334 0.4452 0.035 Uiso 1 1 calc R . .
C6 C 0.92112(12) 0.00111(9) 0.43656(5) 0.0306(3) Uani 1 1 d . . .
C7 C 0.85988(12) -0.07464(8) 0.45548(5) 0.0325(3) Uani 1 1 d . . .
H7 H 0.8755 -0.1302 0.4387 0.039 Uiso 1 1 calc R . .
C8 C 0.77685(12) -0.06876(8) 0.49845(5) 0.0291(3) Uani 1 1 d . . .
H8 H 0.7348 -0.1204 0.5115 0.035 Uiso 1 1 calc R . .
C9 C 0.75363(11) 0.01390(7) 0.52348(5) 0.0237(2) Uani 1 1 d . . .
C10 C 0.54914(12) 0.11054(8) 0.63391(5) 0.0290(3) Uani 1 1 d . . .
C11 C 0.57920(15) 0.08394(9) 0.68646(6) 0.0392(3) Uani 1 1 d . . .
H11 H 0.6602 0.0578 0.6939 0.047 Uiso 1 1 calc R . .
C12 C 0.49150(18) 0.09546(11) 0.72788(6) 0.0519(4) Uani 1 1 d . . .
H12 H 0.5123 0.0773 0.7637 0.062 Uiso 1 1 calc R . .
C13 C 0.37366(17) 0.13330(11) 0.71723(7) 0.0562(5) Uani 1 1 d . . .
H13 H 0.3131 0.1406 0.7457 0.067 Uiso 1 1 calc R . .
C14 C 0.34377(15) 0.16050(10) 0.66550(7) 0.0517(4) Uani 1 1 d . . .
H14 H 0.2628 0.1870 0.6584 0.062 Uiso 1 1 calc R . .
C15 C 0.43068(13) 0.14952(9) 0.62371(6) 0.0384(3) Uani 1 1 d . . .
H15 H 0.4096 0.1686 0.5880 0.046 Uiso 1 1 calc R . .
C16 C 0.61677(12) -0.06064(7) 0.59207(5) 0.0269(3) Uani 1 1 d . . .
H16A H 0.6011 -0.0501 0.6312 0.032 Uiso 1 1 calc R . .
H16B H 0.6801 -0.1092 0.5890 0.032 Uiso 1 1 calc R . .
C17 C 0.49239(12) -0.08979(8) 0.56567(5) 0.0302(3) Uani 1 1 d . . .
H17A H 0.5077 -0.1031 0.5268 0.036 Uiso 1 1 calc R . .
H17B H 0.4287 -0.0413 0.5679 0.036 Uiso 1 1 calc R . .
C18 C 0.43941(13) -0.17259(8) 0.59427(5) 0.0332(3) Uani 1 1 d . . .
H18A H 0.3650 -0.1950 0.5734 0.040 Uiso 1 1 calc R . .
H18B H 0.5062 -0.2192 0.5939 0.040 Uiso 1 1 calc R . .
C19 C 0.39808(12) -0.15668(8) 0.65219(5) 0.0297(3) Uani 1 1 d . . .
C20 C 0.46282(14) -0.19248(10) 0.69585(6) 0.0432(3) Uani 1 1 d . . .
H20 H 0.5372 -0.2275 0.6897 0.052 Uiso 1 1 calc R . .
C21 C 0.42098(16) -0.17813(11) 0.74854(7) 0.0534(4) Uani 1 1 d . . .
H21 H 0.4676 -0.2027 0.7781 0.064 Uiso 1 1 calc R . .
C22 C 0.31342(15) -0.12903(11) 0.75851(6) 0.0489(4) Uani 1 1 d . . .
H22 H 0.2846 -0.1198 0.7947 0.059 Uiso 1 1 calc R . .
C23 C 0.24780(16) -0.09331(12) 0.71565(7) 0.0563(4) Uani 1 1 d . . .
H23 H 0.1727 -0.0592 0.7220 0.068 Uiso 1 1 calc R . .
C24 C 0.29040(15) -0.10668(11) 0.66332(6) 0.0485(4) Uani 1 1 d . . .
H24 H 0.2443 -0.0808 0.6341 0.058 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.3811(14) . ?
N1 C9 1.3863(15) . ?
N1 C16 1.4838(15) . ?
N2 O2 1.2256(17) . ?
N2 O3 1.2272(16) . ?
N2 C6 1.4654(17) . ?
O1 C3 1.2448(15) . ?
C1 C2 1.3581(17) . ?
C1 C10 1.4905(17) . ?
C2 C3 1.4214(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4647(16) . ?
C4 C5 1.3989(17) . ?
C4 C9 1.4073(16) . ?
C5 C6 1.3661(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3901(19) . ?
C7 C8 1.3698(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4128(16) . ?
C8 H8 0.9500 . ?
C10 C15 1.3905(18) . ?
C10 C11 1.3907(19) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.5153(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5373(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5094(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3795(19) . ?
C19 C24 1.380(2) . ?
C20 C21 1.386(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.366(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(2) . ?
C23 H23 0.9500 . ?
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
C1 N1 C9 119.52(9) . . ?
C1 N1 C16 120.90(10) . . ?
C9 N1 C16 119.58(9) . . ?
O2 N2 O3 123.75(13) . . ?
O2 N2 C6 118.07(12) . . ?
O3 N2 C6 118.16(13) . . ?
C2 C1 N1 121.83(11) . . ?
C2 C1 C10 119.02(10) . . ?
N1 C1 C10 119.15(10) . . ?
C1 C2 C3 122.94(11) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
O1 C3 C2 124.52(11) . . ?
O1 C3 C4 121.18(12) . . ?
C2 C3 C4 114.30(10) . . ?
C5 C4 C9 119.70(11) . . ?
C5 C4 C3 119.03(11) . . ?
C9 C4 C3 121.27(11) . . ?
C6 C5 C4 119.48(11) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 121.77(12) . . ?
C5 C6 N2 119.09(12) . . ?
C7 C6 N2 119.14(12) . . ?
C8 C7 C6 119.72(11) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.16(11) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
N1 C9 C4 119.91(10) . . ?
N1 C9 C8 120.96(10) . . ?
C4 C9 C8 119.13(11) . . ?
C15 C10 C11 119.37(13) . . ?
C15 C10 C1 118.73(12) . . ?
C11 C10 C1 121.80(12) . . ?
C12 C11 C10 120.13(14) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.07(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.11(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.42(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 119.90(14) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
N1 C16 C17 113.68(10) . . ?
N1 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
N1 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C18 110.30(10) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 113.95(10) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C24 117.21(13) . . ?
C20 C19 C18 122.32(12) . . ?
C24 C19 C18 120.45(12) . . ?
C19 C20 C21 120.97(14) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 120.74(14) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 119.04(15) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 120.17(15) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.87(14) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?

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
C9 N1 C1 C2 -3.03(17) . . . . ?
C16 N1 C1 C2 177.42(11) . . . . ?
C9 N1 C1 C10 175.96(10) . . . . ?
C16 N1 C1 C10 -3.60(16) . . . . ?
N1 C1 C2 C3 -1.56(19) . . . . ?
C10 C1 C2 C3 179.45(11) . . . . ?
C1 C2 C3 O1 -176.60(12) . . . . ?
C1 C2 C3 C4 3.79(18) . . . . ?
O1 C3 C4 C5 -1.77(18) . . . . ?
C2 C3 C4 C5 177.85(11) . . . . ?
O1 C3 C4 C9 178.66(11) . . . . ?
C2 C3 C4 C9 -1.72(17) . . . . ?
C9 C4 C5 C6 1.17(17) . . . . ?
C3 C4 C5 C6 -178.41(11) . . . . ?
C4 C5 C6 C7 0.65(18) . . . . ?
C4 C5 C6 N2 -179.45(10) . . . . ?
O2 N2 C6 C5 2.09(18) . . . . ?
O3 N2 C6 C5 -179.31(12) . . . . ?
O2 N2 C6 C7 -178.01(12) . . . . ?
O3 N2 C6 C7 0.59(18) . . . . ?
C5 C6 C7 C8 -1.21(19) . . . . ?
N2 C6 C7 C8 178.89(11) . . . . ?
C6 C7 C8 C9 -0.07(18) . . . . ?
C1 N1 C9 C4 4.97(16) . . . . ?
C16 N1 C9 C4 -175.47(10) . . . . ?
C1 N1 C9 C8 -174.75(11) . . . . ?
C16 N1 C9 C8 4.81(16) . . . . ?
C5 C4 C9 N1 177.89(10) . . . . ?
C3 C4 C9 N1 -2.55(17) . . . . ?
C5 C4 C9 C8 -2.39(17) . . . . ?
C3 C4 C9 C8 177.18(11) . . . . ?
C7 C8 C9 N1 -178.44(11) . . . . ?
C7 C8 C9 C4 1.84(17) . . . . ?
C2 C1 C10 C15 68.00(16) . . . . ?
N1 C1 C10 C15 -111.01(13) . . . . ?
C2 C1 C10 C11 -108.36(14) . . . . ?
N1 C1 C10 C11 72.62(16) . . . . ?
C15 C10 C11 C12 0.6(2) . . . . ?
C1 C10 C11 C12 176.96(13) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C11 C10 C15 C14 -0.7(2) . . . . ?
C1 C10 C15 C14 -177.19(12) . . . . ?
C1 N1 C16 C17 92.07(13) . . . . ?
C9 N1 C16 C17 -87.49(13) . . . . ?
N1 C16 C17 C18 -178.25(10) . . . . ?
C16 C17 C18 C19 66.02(14) . . . . ?
C17 C18 C19 C20 -111.48(15) . . . . ?
C17 C18 C19 C24 70.16(16) . . . . ?
C24 C19 C20 C21 -0.3(2) . . . . ?
C18 C19 C20 C21 -178.68(13) . . . . ?
C19 C20 C21 C22 0.9(2) . . . . ?
C20 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C19 0.8(3) . . . . ?
C20 C19 C24 C23 -0.6(2) . . . . ?
C18 C19 C24 C23 177.87(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_ch_mm181
_database_code_depnum_ccdc_archive 'CCDC 934416'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


#==============================================================================



# CHEMICAL DATA


_chemical_name_systematic        
;
3,6-bis(4-ethylphenyl)-4H-chromen-4-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 O2'
_chemical_formula_sum            'C25 H22 O2'
_chemical_formula_weight         354.43

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


#==============================================================================



# CRYSTAL DATA

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   P21/n

_symmetry_space_group_name_Hall  '-P 2yn'

_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   5.8177(4)
_cell_length_b                   10.2341(6)
_cell_length_c                   31.4579(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.982(2)
_cell_angle_gamma                90.00
_cell_volume                     1865.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6568
_cell_measurement_theta_min      5.199
_cell_measurement_theta_max      59.492

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'


#==============================================================================

# EXPERIMENTAL DATA


_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24058
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4514
_reflns_number_gt                3522
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.9533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4514
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#==============================================================================



# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10467(18) 0.36911(11) 0.09657(3) 0.0383(3) Uani 1 1 d . . .
O2 O 0.66888(18) 0.60585(11) 0.09348(4) 0.0390(3) Uani 1 1 d . . .
C1 C 0.1123(3) 0.46732(15) 0.06809(5) 0.0333(3) Uani 1 1 d . . .
H1 H -0.0195 0.4789 0.0484 0.040 Uiso 1 1 calc R . .
C2 C 0.2895(2) 0.55046(14) 0.06504(4) 0.0292(3) Uani 1 1 d . . .
C3 C 0.4978(2) 0.53597(14) 0.09442(5) 0.0292(3) Uani 1 1 d . . .
C4 C 0.4861(2) 0.43062(14) 0.12597(4) 0.0293(3) Uani 1 1 d . . .
C5 C 0.2921(3) 0.35137(15) 0.12554(5) 0.0330(3) Uani 1 1 d . A .
C6 C 0.2742(2) 0.65218(14) 0.03142(5) 0.0293(3) Uani 1 1 d . . .
C7 C 0.0798(3) 0.73227(15) 0.02449(5) 0.0344(3) Uani 1 1 d . . .
H7 H -0.0423 0.7249 0.0425 0.041 Uiso 1 1 calc R . .
C8 C 0.0646(3) 0.82232(16) -0.00854(5) 0.0387(4) Uani 1 1 d . . .
H8 H -0.0686 0.8761 -0.0127 0.046 Uiso 1 1 calc R . .
C9 C 0.2386(3) 0.83617(15) -0.03580(5) 0.0364(4) Uani 1 1 d . . .
C10 C 0.4329(3) 0.75681(15) -0.02832(5) 0.0345(3) Uani 1 1 d . . .
H10 H 0.5551 0.7644 -0.0463 0.041 Uiso 1 1 calc R . .
C11 C 0.4516(2) 0.66755(15) 0.00466(5) 0.0313(3) Uani 1 1 d . . .
H11 H 0.5870 0.6158 0.0092 0.038 Uiso 1 1 calc R . .
C12 C 0.2208(3) 0.93150(19) -0.07254(6) 0.0517(5) Uani 1 1 d . . .
H12A H 0.2023 0.8816 -0.0996 0.062 Uiso 1 1 calc R . .
H12B H 0.0801 0.9850 -0.0709 0.062 Uiso 1 1 calc R . .
C13 C 0.4245(4) 1.0215(2) -0.07385(8) 0.0672(6) Uani 1 1 d . . .
H13A H 0.4482 1.0693 -0.0468 0.101 Uiso 1 1 calc R . .
H13B H 0.3954 1.0838 -0.0974 0.101 Uiso 1 1 calc R . .
H13C H 0.5627 0.9702 -0.0782 0.101 Uiso 1 1 calc R . .
C14 C 0.6690(3) 0.40672(15) 0.15708(5) 0.0318(3) Uani 1 1 d . A .
H14 H 0.8035 0.4596 0.1577 0.038 Uiso 1 1 calc R . .
C15 C 0.6583(3) 0.30778(15) 0.18698(5) 0.0334(3) Uani 1 1 d . . .
C16 C 0.4590(3) 0.22972(17) 0.18475(5) 0.0413(4) Uani 1 1 d . A .
H16 H 0.4493 0.1609 0.2048 0.050 Uiso 1 1 calc R . .
C17 C 0.2780(3) 0.24980(18) 0.15458(5) 0.0417(4) Uani 1 1 d . . .
H17 H 0.1454 0.1953 0.1535 0.050 Uiso 1 1 calc R A .
C18A C 0.8472(9) 0.2811(7) 0.22152(14) 0.0341(5) Uani 0.63(4) 1 d PG A 1
C19A C 0.9593(17) 0.3873(7) 0.2416(3) 0.0379(15) Uani 0.63(4) 1 d PG A 1
H19A H 0.9217 0.4736 0.2323 0.046 Uiso 0.63(4) 1 calc PR A 1
C20A C 1.1265(19) 0.3672(7) 0.2753(3) 0.0449(15) Uani 0.63(4) 1 d PG A 1
H20A H 1.2031 0.4397 0.2890 0.054 Uiso 0.63(4) 1 calc PR A 1
C21A C 1.1815(11) 0.2409(8) 0.28889(10) 0.0493(6) Uani 0.63(4) 1 d PG A 1
C22A C 1.0694(7) 0.1348(7) 0.2688(2) 0.0403(12) Uani 0.63(4) 1 d PG A 1
H22A H 1.1070 0.0485 0.2781 0.048 Uiso 0.63(4) 1 calc PR A 1
C23A C 0.9022(10) 0.1549(7) 0.2351(3) 0.0300(12) Uani 0.63(4) 1 d PG A 1
H23A H 0.8256 0.0823 0.2214 0.036 Uiso 0.63(4) 1 calc PR A 1
C18B C 0.8530(14) 0.2925(14) 0.2223(2) 0.0341(5) Uani 0.37(4) 1 d PG A 2
C19B C 1.000(2) 0.3945(10) 0.2355(3) 0.0294(18) Uani 0.37(4) 1 d PG A 2
H19B H 0.9829 0.4775 0.2220 0.035 Uiso 0.37(4) 1 calc PR A 2
C20B C 1.172(2) 0.3751(6) 0.2683(3) 0.0370(18) Uani 0.37(4) 1 d PG A 2
H20B H 1.2728 0.4448 0.2773 0.044 Uiso 0.37(4) 1 calc PR A 2
C21B C 1.1974(6) 0.2537(5) 0.28801(10) 0.0493(6) Uani 0.37(4) 1 d PG A 2
C22B C 1.050(2) 0.1518(10) 0.2748(3) 0.037(2) Uani 0.37(4) 1 d PG A 2
H22B H 1.0675 0.0688 0.2883 0.045 Uiso 0.37(4) 1 calc PR A 2
C23B C 0.878(2) 0.1711(15) 0.2420(4) 0.038(2) Uani 0.37(4) 1 d PG A 2
H23B H 0.7776 0.1014 0.2329 0.045 Uiso 0.37(4) 1 calc PR A 2
C24 C 1.3695(5) 0.2237(2) 0.32613(8) 0.0791(8) Uani 1 1 d R . .
H24A H 1.3440 0.1374 0.3392 0.095 Uiso 0.520(7) 1 calc PR B 1
H24B H 1.5195 0.2188 0.3136 0.095 Uiso 0.520(7) 1 calc PR B 1
H24C H 1.2978 0.2289 0.3519 0.095 Uiso 0.480(7) 1 d PR B 2
H24D H 1.4305 0.1346 0.3240 0.095 Uiso 0.480(7) 1 d PR B 2
C25A C 1.3933(12) 0.3118(5) 0.35824(15) 0.079(2) Uani 0.520(7) 1 d P A 1
H25A H 1.4348 0.3969 0.3469 0.119 Uiso 0.520(7) 1 calc PR B 1
H25B H 1.5150 0.2828 0.3797 0.119 Uiso 0.520(7) 1 calc PR B 1
H25C H 1.2474 0.3194 0.3714 0.119 Uiso 0.520(7) 1 calc PR B 1
C25B C 1.5559(10) 0.3043(6) 0.3316(2) 0.076(2) Uani 0.480(7) 1 d P A 2
H25D H 1.6438 0.2994 0.3064 0.114 Uiso 0.480(7) 1 calc PR B 2
H25E H 1.6543 0.2772 0.3569 0.114 Uiso 0.480(7) 1 calc PR B 2
H25F H 1.5038 0.3943 0.3353 0.114 Uiso 0.480(7) 1 calc PR B 2



#==============================================================================



# MOLECULAR GEOMETRY


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.3496(19) . ?
O1 C5 1.3708(18) . ?
O2 C3 1.2279(17) . ?
C1 C2 1.347(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.4664(19) . ?
C2 C6 1.481(2) . ?
C3 C4 1.471(2) . ?
C4 C5 1.389(2) . ?
C4 C14 1.403(2) . ?
C5 C17 1.391(2) . ?
C6 C11 1.396(2) . ?
C6 C7 1.398(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(2) . ?
C9 C12 1.509(2) . ?
C10 C11 1.380(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.405(2) . ?
C15 C18A 1.502(3) . ?
C15 C18B 1.524(3) . ?
C16 C17 1.370(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18A C19A 1.3900 . ?
C18A C23A 1.3900 . ?
C19A C20A 1.3900 . ?
C19A H19A 0.9500 . ?
C20A C21A 1.3900 . ?
C20A H20A 0.9500 . ?
C21A C22A 1.3900 . ?
C21A C24 1.542(4) . ?
C22A C23A 1.3900 . ?
C22A H22A 0.9500 . ?
C23A H23A 0.9500 . ?
C18B C19B 1.3900 . ?
C18B C23B 1.3900 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B C22B 1.3900 . ?
C21B C24 1.5254 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B H23B 0.9500 . ?
C24 C25A 1.352(5) . ?
C24 C25B 1.361(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 H24C 0.9451 . ?
C24 H24D 0.9823 . ?
C25A H24C 1.0241 . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 118.03(12) . . ?
C2 C1 O1 125.96(14) . . ?
C2 C1 H1 117.0 . . ?
O1 C1 H1 117.0 . . ?
C1 C2 C3 119.15(14) . . ?
C1 C2 C6 119.74(13) . . ?
C3 C2 C6 121.08(12) . . ?
O2 C3 C2 123.58(14) . . ?
O2 C3 C4 121.88(13) . . ?
C2 C3 C4 114.54(12) . . ?
C5 C4 C14 118.13(14) . . ?
C5 C4 C3 120.42(13) . . ?
C14 C4 C3 121.44(13) . . ?
O1 C5 C4 121.86(14) . . ?
O1 C5 C17 116.55(13) . . ?
C4 C5 C17 121.59(14) . . ?
C11 C6 C7 118.03(14) . . ?
C11 C6 C2 120.53(13) . . ?
C7 C6 C2 121.39(13) . . ?
C8 C7 C6 120.33(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.85(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 117.36(15) . . ?
C8 C9 C12 122.23(15) . . ?
C10 C9 C12 120.41(16) . . ?
C11 C10 C9 121.46(15) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 120.94(14) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C9 114.51(15) . . ?
C13 C12 H12A 108.6 . . ?
C9 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C9 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C4 121.60(14) . . ?
C15 C14 H14 119.2 . . ?
C4 C14 H14 119.2 . . ?
C14 C15 C16 117.83(14) . . ?
C14 C15 C18A 123.4(3) . . ?
C16 C15 C18A 118.8(3) . . ?
C14 C15 C18B 119.6(5) . . ?
C16 C15 C18B 122.4(5) . . ?
C18A C15 C18B 4.6(7) . . ?
C17 C16 C15 122.04(15) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C5 118.79(15) . . ?
C16 C17 H17 120.6 . . ?
C5 C17 H17 120.6 . . ?
C19A C18A C23A 120.0 . . ?
C19A C18A C15 118.1(4) . . ?
C23A C18A C15 121.8(4) . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C20A C21A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A C24 122.0(4) . . ?
C20A C21A C24 118.0(4) . . ?
C23A C22A C21A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C22A C23A C18A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C18A C23A H23A 120.0 . . ?
C19B C18B C23B 120.0 . . ?
C19B C18B C15 122.7(7) . . ?
C23B C18B C15 117.3(7) . . ?
C20B C19B C18B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B C24 115.4 . . ?
C20B C21B C24 124.5 . . ?
C21B C22B C23B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C22B C23B C18B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C18B C23B H23B 120.0 . . ?
C25A C24 C25B 58.2(4) . . ?
C25A C24 C21B 118.1(3) . . ?
C25B C24 C21B 116.0(3) . . ?
C25A C24 C21A 120.8(3) . . ?
C25B C24 C21A 122.1(4) . . ?
C21B C24 C21A 6.1(4) . . ?
C25A C24 H24A 107.1 . . ?
C25B C24 H24A 129.4 . . ?
C21B C24 H24A 113.2 . . ?
C21A C24 H24A 107.1 . . ?
C25A C24 H24B 107.1 . . ?
C25B C24 H24B 50.2 . . ?
C21B C24 H24B 103.8 . . ?
C21A C24 H24B 107.1 . . ?
H24A C24 H24B 106.8 . . ?
C25A C24 H24C 49.1 . . ?
C25B C24 H24C 105.3 . . ?
C21B C24 H24C 110.8 . . ?
C21A C24 H24C 108.0 . . ?
H24A C24 H24C 66.6 . . ?
H24B C24 H24C 144.6 . . ?
C25A C24 H24D 130.9 . . ?
C25B C24 H24D 106.4 . . ?
C21B C24 H24D 110.5 . . ?
C21A C24 H24D 106.9 . . ?
H24A C24 H24D 43.0 . . ?
H24B C24 H24D 65.8 . . ?
H24C C24 H24D 107.4 . . ?
C24 C25A H24C 44.2 . . ?
C24 C25A H25A 109.5 . . ?
H24C C25A H25A 144.3 . . ?
C24 C25A H25B 109.5 . . ?
H24C C25A H25B 103.4 . . ?
C24 C25A H25C 109.5 . . ?
H24C C25A H25C 70.9 . . ?
C24 C25B H25D 109.5 . . ?
C24 C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C24 C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 0.6(2) . . . . ?
O1 C1 C2 C3 0.6(2) . . . . ?
O1 C1 C2 C6 178.79(13) . . . . ?
C1 C2 C3 O2 178.75(15) . . . . ?
C6 C2 C3 O2 0.6(2) . . . . ?
C1 C2 C3 C4 -1.84(19) . . . . ?
C6 C2 C3 C4 179.99(12) . . . . ?
O2 C3 C4 C5 -178.51(14) . . . . ?
C2 C3 C4 C5 2.07(19) . . . . ?
O2 C3 C4 C14 1.2(2) . . . . ?
C2 C3 C4 C14 -178.17(13) . . . . ?
C1 O1 C5 C4 -0.3(2) . . . . ?
C1 O1 C5 C17 179.63(14) . . . . ?
C14 C4 C5 O1 179.18(13) . . . . ?
C3 C4 C5 O1 -1.1(2) . . . . ?
C14 C4 C5 C17 -0.8(2) . . . . ?
C3 C4 C5 C17 178.99(14) . . . . ?
C1 C2 C6 C11 -129.21(15) . . . . ?
C3 C2 C6 C11 48.95(19) . . . . ?
C1 C2 C6 C7 48.5(2) . . . . ?
C3 C2 C6 C7 -133.32(15) . . . . ?
C11 C6 C7 C8 1.0(2) . . . . ?
C2 C6 C7 C8 -176.75(13) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C7 C8 C9 C12 178.40(15) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C12 C9 C10 C11 -179.00(15) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C7 C6 C11 C10 -1.6(2) . . . . ?
C2 C6 C11 C10 176.18(13) . . . . ?
C8 C9 C12 C13 128.2(2) . . . . ?
C10 C9 C12 C13 -52.5(3) . . . . ?
C5 C4 C14 C15 -0.5(2) . . . . ?
C3 C4 C14 C15 179.75(13) . . . . ?
C4 C14 C15 C16 1.2(2) . . . . ?
C4 C14 C15 C18A -178.3(3) . . . . ?
C4 C14 C15 C18B -175.2(6) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C18A C15 C16 C17 178.8(3) . . . . ?
C18B C15 C16 C17 175.6(6) . . . . ?
C15 C16 C17 C5 -0.5(3) . . . . ?
O1 C5 C17 C16 -178.69(15) . . . . ?
C4 C5 C17 C16 1.3(2) . . . . ?
C14 C15 C18A C19A 39.4(7) . . . . ?
C16 C15 C18A C19A -140.1(5) . . . . ?
C18B C15 C18A C19A 3(8) . . . . ?
C14 C15 C18A C23A -144.1(5) . . . . ?
C16 C15 C18A C23A 36.4(6) . . . . ?
C18B C15 C18A C23A 179(100) . . . . ?
C23A C18A C19A C20A 0.0 . . . . ?
C15 C18A C19A C20A 176.5(4) . . . . ?
C18A C19A C20A C21A 0.0 . . . . ?
C19A C20A C21A C22A 0.0 . . . . ?
C19A C20A C21A C24 179.5(4) . . . . ?
C20A C21A C22A C23A 0.0 . . . . ?
C24 C21A C22A C23A -179.5(4) . . . . ?
C21A C22A C23A C18A 0.0 . . . . ?
C19A C18A C23A C22A 0.0 . . . . ?
C15 C18A C23A C22A -176.4(4) . . . . ?
C14 C15 C18B C19B 22.6(12) . . . . ?
C16 C15 C18B C19B -153.6(8) . . . . ?
C18A C15 C18B C19B 168(9) . . . . ?
C14 C15 C18B C23B -158.4(8) . . . . ?
C16 C15 C18B C23B 25.3(8) . . . . ?
C18A C15 C18B C23B -13(8) . . . . ?
C23B C18B C19B C20B 0.0 . . . . ?
C15 C18B C19B C20B 178.9(7) . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C19B C20B C21B C22B 0.0 . . . . ?
C19B C20B C21B C24 -175.9 . . . . ?
C20B C21B C22B C23B 0.0 . . . . ?
C24 C21B C22B C23B 176.3 . . . . ?
C21B C22B C23B C18B 0.0 . . . . ?
C19B C18B C23B C22B 0.0 . . . . ?
C15 C18B C23B C22B -179.0(7) . . . . ?
C22B C21B C24 C25A -132.9(9) . . . . ?
C20B C21B C24 C25A 43.2(9) . . . . ?
C22B C21B C24 C25B 160.9(9) . . . . ?
C20B C21B C24 C25B -23.0(9) . . . . ?
C22B C21B C24 C21A -15(3) . . . . ?
C20B C21B C24 C21A 161(3) . . . . ?
C22A C21A C24 C25A -145.8(6) . . . . ?
C20A C21A C24 C25A 34.7(6) . . . . ?
C22A C21A C24 C25B 144.7(8) . . . . ?
C20A C21A C24 C25B -34.8(7) . . . . ?
C22A C21A C24 C21B 149(3) . . . . ?
C20A C21A C24 C21B -31(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.041

#=====================  End of ch_mm181 =================================

#=====================  End of CIF submission =================================
####################################################################### 
# 
# 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_is_mm127
_database_code_depnum_ccdc_archive 'CCDC 934417'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97


#==============================================================================



# CHEMICAL DATA


_chemical_name_systematic        
;
1-(4-Methoxybenzyl)-6-nitro-2-(4-tolyl)quinolin-4(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O4'
_chemical_formula_sum            'C24 H20 N2 O4'
_chemical_formula_weight         400.42

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'


#==============================================================================



# CRYSTAL DATA 
_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   'P 21/c'

_symmetry_space_group_name_Hall  '-P 2ybc'

_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4745(6)
_cell_length_b                   10.6976(6)
_cell_length_c                   17.8031(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.384(3)
_cell_angle_gamma                90.00
_cell_volume                     1994.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2159
_cell_measurement_theta_min      5.444
_cell_measurement_theta_max      48.799

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'


#==============================================================================

# EXPERIMENTAL DATA


_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19220
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0722
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4810
_reflns_number_gt                2565
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.1947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4810
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#==============================================================================



# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06564(14) 0.69885(13) -0.08405(7) 0.0434(4) Uani 1 1 d . . .
O2 O -0.40772(17) 0.39905(16) -0.04269(10) 0.0681(5) Uani 1 1 d . . .
O3 O -0.4259(2) 0.3115(2) 0.06566(11) 0.1002(8) Uani 1 1 d . . .
O4 O 0.32808(13) 0.32583(13) 0.36684(8) 0.0466(4) Uani 1 1 d . . .
N1 N 0.01068(15) 0.69647(14) 0.14363(8) 0.0296(4) Uani 1 1 d . . .
N2 N -0.37626(19) 0.38631(19) 0.02365(12) 0.0574(6) Uani 1 1 d . . .
C1 C -0.04252(19) 0.69933(18) -0.01523(11) 0.0330(5) Uani 1 1 d . . .
C2 C -0.11168(18) 0.61799(16) 0.03636(10) 0.0293(4) Uani 1 1 d . . .
C3 C -0.08279(18) 0.61745(17) 0.11391(10) 0.0297(5) Uani 1 1 d . . .
C4 C 0.07625(18) 0.77500(17) 0.09638(10) 0.0297(4) Uani 1 1 d . . .
C5 C 0.05084(19) 0.77687(18) 0.02122(10) 0.0354(5) Uani 1 1 d . . .
H5 H 0.0979 0.8330 -0.0088 0.042 Uiso 1 1 calc R . .
C6 C -0.20877(19) 0.54154(18) 0.00736(11) 0.0351(5) Uani 1 1 d . . .
H6 H -0.2293 0.5423 -0.0449 0.042 Uiso 1 1 calc R . .
C7 C -0.27406(19) 0.46568(19) 0.05457(12) 0.0380(5) Uani 1 1 d . . .
C8 C -0.24525(19) 0.4611(2) 0.13094(11) 0.0410(5) Uani 1 1 d . . .
H8 H -0.2910 0.4062 0.1625 0.049 Uiso 1 1 calc R . .
C9 C -0.15109(19) 0.53559(19) 0.16071(11) 0.0369(5) Uani 1 1 d . . .
H9 H -0.1313 0.5324 0.2130 0.044 Uiso 1 1 calc R . .
C10 C 0.02997(19) 0.70494(18) 0.22574(10) 0.0318(5) Uani 1 1 d . . .
H10A H -0.0545 0.7012 0.2494 0.038 Uiso 1 1 calc R . .
H10B H 0.0678 0.7875 0.2379 0.038 Uiso 1 1 calc R . .
C11 C 0.11412(18) 0.60483(17) 0.26046(10) 0.0282(4) Uani 1 1 d . . .
C12 C 0.15097(18) 0.49707(18) 0.22344(11) 0.0339(5) Uani 1 1 d . . .
H12 H 0.1263 0.4850 0.1723 0.041 Uiso 1 1 calc R . .
C13 C 0.22336(18) 0.40713(18) 0.26050(11) 0.0353(5) Uani 1 1 d . . .
H13 H 0.2487 0.3342 0.2343 0.042 Uiso 1 1 calc R . .
C14 C 0.25925(18) 0.42199(18) 0.33501(11) 0.0341(5) Uani 1 1 d . . .
C15 C 0.22540(19) 0.53016(19) 0.37241(11) 0.0393(5) Uani 1 1 d . . .
H15 H 0.2511 0.5424 0.4234 0.047 Uiso 1 1 calc R . .
C16 C 0.1536(2) 0.62040(19) 0.33464(11) 0.0371(5) Uani 1 1 d . . .
H16 H 0.1310 0.6947 0.3603 0.045 Uiso 1 1 calc R . .
C17 C 0.3719(2) 0.3413(2) 0.44284(13) 0.0604(7) Uani 1 1 d . . .
H17A H 0.4283 0.4143 0.4464 0.091 Uiso 1 1 calc R . .
H17B H 0.4189 0.2665 0.4591 0.091 Uiso 1 1 calc R . .
H17C H 0.2985 0.3538 0.4751 0.091 Uiso 1 1 calc R . .
C18 C 0.17549(18) 0.86079(18) 0.12828(10) 0.0316(5) Uani 1 1 d . . .
C19 C 0.28640(19) 0.81715(19) 0.16440(11) 0.0358(5) Uani 1 1 d . . .
H19 H 0.2987 0.7299 0.1713 0.043 Uiso 1 1 calc R . .
C20 C 0.37844(19) 0.90034(19) 0.19018(11) 0.0366(5) Uani 1 1 d . . .
H20 H 0.4534 0.8690 0.2146 0.044 Uiso 1 1 calc R . .
C21 C 0.36412(19) 1.02849(19) 0.18126(11) 0.0362(5) Uani 1 1 d . . .
C22 C 0.25434(19) 1.07124(19) 0.14347(11) 0.0366(5) Uani 1 1 d . . .
H22 H 0.2431 1.1584 0.1356 0.044 Uiso 1 1 calc R . .
C23 C 0.16173(19) 0.98918(18) 0.11728(10) 0.0348(5) Uani 1 1 d . . .
H23 H 0.0880 1.0205 0.0915 0.042 Uiso 1 1 calc R . .
C24 C 0.4616(2) 1.1191(2) 0.21348(13) 0.0502(6) Uani 1 1 d . . .
H24A H 0.4739 1.1877 0.1779 0.075 Uiso 1 1 calc R . .
H24B H 0.5428 1.0756 0.2225 0.075 Uiso 1 1 calc R . .
H24C H 0.4312 1.1528 0.2610 0.075 Uiso 1 1 calc R . .



#==============================================================================



# MOLECULAR GEOMETRY


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.243(2) . ?
O2 N2 1.226(2) . ?
O3 N2 1.220(2) . ?
O4 C14 1.371(2) . ?
O4 C17 1.428(2) . ?
N1 C4 1.383(2) . ?
N1 C3 1.389(2) . ?
N1 C10 1.474(2) . ?
N2 C7 1.463(3) . ?
C1 C5 1.426(3) . ?
C1 C2 1.469(3) . ?
C2 C6 1.394(2) . ?
C2 C3 1.406(2) . ?
C3 C9 1.415(3) . ?
C4 C5 1.358(2) . ?
C4 C18 1.489(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C8 C9 1.365(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.510(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.384(2) . ?
C11 C12 1.387(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.394(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(3) . ?
C21 C24 1.511(3) . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C14 O4 C17 117.28(17) . . ?
C4 N1 C3 119.60(15) . . ?
C4 N1 C10 120.52(15) . . ?
C3 N1 C10 119.60(16) . . ?
O3 N2 O2 123.70(19) . . ?
O3 N2 C7 117.94(19) . . ?
O2 N2 C7 118.36(19) . . ?
O1 C1 C5 124.47(18) . . ?
O1 C1 C2 121.77(17) . . ?
C5 C1 C2 113.76(16) . . ?
C6 C2 C3 119.92(18) . . ?
C6 C2 C1 118.82(16) . . ?
C3 C2 C1 121.25(17) . . ?
N1 C3 C2 120.30(17) . . ?
N1 C3 C9 120.95(17) . . ?
C2 C3 C9 118.74(17) . . ?
C5 C4 N1 121.32(17) . . ?
C5 C4 C18 119.02(18) . . ?
N1 C4 C18 119.65(16) . . ?
C4 C5 C1 123.75(19) . . ?
C4 C5 H5 118.1 . . ?
C1 C5 H5 118.1 . . ?
C7 C6 C2 119.53(18) . . ?
C7 C6 H6 120.2 . . ?
C2 C6 H6 120.2 . . ?
C6 C7 C8 121.66(18) . . ?
C6 C7 N2 119.11(18) . . ?
C8 C7 N2 119.23(19) . . ?
C9 C8 C7 119.88(19) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C3 120.23(18) . . ?
C8 C9 H9 119.9 . . ?
C3 C9 H9 119.9 . . ?
N1 C10 C11 115.29(15) . . ?
N1 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C16 C11 C12 118.23(17) . . ?
C16 C11 C10 117.59(16) . . ?
C12 C11 C10 124.15(16) . . ?
C13 C12 C11 120.48(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.82(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
O4 C14 C13 116.07(18) . . ?
O4 C14 C15 124.49(18) . . ?
C13 C14 C15 119.44(17) . . ?
C14 C15 C16 119.35(18) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 121.64(18) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.47(17) . . ?
C23 C18 C4 119.00(16) . . ?
C19 C18 C4 122.38(17) . . ?
C20 C19 C18 120.27(18) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 121.70(18) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 117.68(18) . . ?
C20 C21 C24 121.35(19) . . ?
C22 C21 C24 120.95(19) . . ?
C23 C22 C21 121.23(19) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C18 120.62(18) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C6 -2.2(3) . . . . ?
C5 C1 C2 C6 177.53(17) . . . . ?
O1 C1 C2 C3 178.63(18) . . . . ?
C5 C1 C2 C3 -1.6(3) . . . . ?
C4 N1 C3 C2 -0.6(3) . . . . ?
C10 N1 C3 C2 173.26(16) . . . . ?
C4 N1 C3 C9 179.68(18) . . . . ?
C10 N1 C3 C9 -6.4(3) . . . . ?
C6 C2 C3 N1 -177.74(16) . . . . ?
C1 C2 C3 N1 1.4(3) . . . . ?
C6 C2 C3 C9 2.0(3) . . . . ?
C1 C2 C3 C9 -178.93(18) . . . . ?
C3 N1 C4 C5 0.2(3) . . . . ?
C10 N1 C4 C5 -173.61(17) . . . . ?
C3 N1 C4 C18 179.32(16) . . . . ?
C10 N1 C4 C18 5.5(3) . . . . ?
N1 C4 C5 C1 -0.6(3) . . . . ?
C18 C4 C5 C1 -179.68(18) . . . . ?
O1 C1 C5 C4 -179.0(2) . . . . ?
C2 C1 C5 C4 1.2(3) . . . . ?
C3 C2 C6 C7 -0.7(3) . . . . ?
C1 C2 C6 C7 -179.86(19) . . . . ?
C2 C6 C7 C8 -0.9(3) . . . . ?
C2 C6 C7 N2 179.66(18) . . . . ?
O3 N2 C7 C6 173.8(2) . . . . ?
O2 N2 C7 C6 -6.6(3) . . . . ?
O3 N2 C7 C8 -5.6(3) . . . . ?
O2 N2 C7 C8 174.0(2) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
N2 C7 C8 C9 -179.30(19) . . . . ?
C7 C8 C9 C3 0.0(3) . . . . ?
N1 C3 C9 C8 178.09(18) . . . . ?
C2 C3 C9 C8 -1.6(3) . . . . ?
C4 N1 C10 C11 -102.6(2) . . . . ?
C3 N1 C10 C11 83.6(2) . . . . ?
N1 C10 C11 C16 168.95(18) . . . . ?
N1 C10 C11 C12 -13.0(3) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
C10 C11 C12 C13 -176.93(18) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C17 O4 C14 C13 177.03(19) . . . . ?
C17 O4 C14 C15 -2.7(3) . . . . ?
C12 C13 C14 O4 178.38(17) . . . . ?
C12 C13 C14 C15 -1.9(3) . . . . ?
O4 C14 C15 C16 -178.94(18) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C12 C11 C16 C15 -1.6(3) . . . . ?
C10 C11 C16 C15 176.53(19) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C5 C4 C18 C23 58.0(3) . . . . ?
N1 C4 C18 C23 -121.1(2) . . . . ?
C5 C4 C18 C19 -117.5(2) . . . . ?
N1 C4 C18 C19 63.4(3) . . . . ?
C23 C18 C19 C20 1.6(3) . . . . ?
C4 C18 C19 C20 177.13(19) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C19 C20 C21 C24 176.5(2) . . . . ?
C20 C21 C22 C23 1.4(3) . . . . ?
C24 C21 C22 C23 -176.63(19) . . . . ?
C21 C22 C23 C18 0.2(3) . . . . ?
C19 C18 C23 C22 -1.8(3) . . . . ?
C4 C18 C23 C22 -177.43(18) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_is_mm183
_database_code_depnum_ccdc_archive 'CCDC 934420'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
3,6-bis(4-ethylphenyl)-1-(4-methoxybenzyl)-2-(4-tolyl)quinolin-4(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.97(C40 H37 N O2), 0.03(C32 H28 N O2 Br)'
_chemical_formula_sum            'C39.74 H36.71 Br0.03 N O2'
_chemical_formula_weight         562.69

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5670(5)
_cell_length_b                   12.7739(5)
_cell_length_c                   12.9152(5)
_cell_angle_alpha                109.863(2)
_cell_angle_beta                 101.516(2)
_cell_angle_gamma                105.361(2)
_cell_volume                     1498.23(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5785
_cell_measurement_theta_min      5.865
_cell_measurement_theta_max      59.209

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39715
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0732
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         30.00
_reflns_number_total             8694
_reflns_number_gt                5050
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.4346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8694
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1406
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39309(14) 0.57452(12) 0.30541(11) 0.0201(3) Uani 1 1 d . . .
O1 O 0.25914(13) 0.58020(10) 0.58319(10) 0.0292(3) Uani 1 1 d . . .
O2 O 0.97956(13) 0.65359(13) 0.20478(12) 0.0399(4) Uani 1 1 d . . .
C1 C 0.43630(16) 0.68270(14) 0.40287(13) 0.0191(3) Uani 1 1 d . . .
C2 C 0.52222(17) 0.79019(15) 0.40727(14) 0.0227(4) Uani 1 1 d . . .
H2 H 0.5488 0.7912 0.3415 0.027 Uiso 1 1 calc R . .
C3 C 0.56775(18) 0.89357(15) 0.50644(14) 0.0235(4) Uani 1 1 d . . .
H3 H 0.6267 0.9651 0.5082 0.028 Uiso 1 1 calc R . .
C4 C 0.52973(17) 0.89698(14) 0.60585(13) 0.0215(3) Uani 1 1 d . . .
C5 C 0.44190(17) 0.79217(14) 0.59926(13) 0.0209(3) Uani 1 1 d . . .
H5 H 0.4129 0.7926 0.6644 0.025 Uiso 1 1 calc R . .
C6 C 0.39380(16) 0.68471(14) 0.49961(13) 0.0195(3) Uani 1 1 d . . .
C7 C 0.30028(17) 0.57729(14) 0.49882(13) 0.0202(3) Uani 1 1 d . A .
C8 C 0.26206(17) 0.46867(14) 0.39545(13) 0.0201(3) Uani 1 1 d . . .
C9 C 0.31186(16) 0.47034(14) 0.30568(13) 0.0196(3) Uani 1 1 d . A .
C10 C 0.1633(2) 0.3573(2) 0.39210(15) 0.0205(4) Uani 0.9676(7) 1 d P A 1
C11 C 0.03217(18) 0.35166(15) 0.39515(14) 0.0230(4) Uani 0.9676(7) 1 d P A 1
H11 H 0.0036 0.4161 0.3948 0.028 Uiso 0.9676(7) 1 calc PR A 1
C12 C -0.05870(18) 0.25327(16) 0.39874(15) 0.0248(4) Uani 0.9676(7) 1 d P A 1
H12 H -0.1495 0.2505 0.3984 0.030 Uiso 0.9676(7) 1 calc PR A 1
C13 C -0.01983(18) 0.15882(16) 0.40278(15) 0.0252(4) Uani 0.9676(7) 1 d P A 1
C14 C 0.11270(19) 0.16487(16) 0.39955(16) 0.0278(4) Uani 0.9676(7) 1 d P A 1
H14 H 0.1414 0.1007 0.4007 0.033 Uiso 0.9676(7) 1 calc PR A 1
C15 C 0.20544(19) 0.2639(2) 0.39457(15) 0.0249(4) Uani 0.9676(7) 1 d P A 1
H15 H 0.2957 0.2666 0.3929 0.030 Uiso 0.9676(7) 1 calc PR A 1
C16 C -0.1147(2) 0.05721(17) 0.41652(18) 0.0336(5) Uani 0.9676(7) 1 d P A 1
H16A H -0.2031 0.0699 0.4166 0.040 Uiso 0.9676(7) 1 calc PR A 1
H16B H -0.0725 0.0593 0.4932 0.040 Uiso 0.9676(7) 1 calc PR A 1
C17 C -0.1463(2) -0.06598(19) 0.3236(2) 0.0455(6) Uani 0.9676(7) 1 d P A 1
H17A H -0.2015 -0.0737 0.2489 0.068 Uiso 0.9676(7) 1 calc PR A 1
H17B H -0.1985 -0.1268 0.3448 0.068 Uiso 0.9676(7) 1 calc PR A 1
H17C H -0.0594 -0.0769 0.3172 0.068 Uiso 0.9676(7) 1 calc PR A 1
Br1 Br 0.1842(8) 0.3162(7) 0.3900(5) 0.0205(4) Uani 0.0324(7) 1 d P A 2
C18 C 0.28375(17) 0.35574(14) 0.20555(13) 0.0218(4) Uani 1 1 d . . .
C19 C 0.15309(18) 0.29106(16) 0.12340(15) 0.0271(4) Uani 1 1 d . A .
H19 H 0.0821 0.3236 0.1252 0.033 Uiso 1 1 calc R . .
C20 C 0.1262(2) 0.17836(17) 0.03827(16) 0.0333(4) Uani 1 1 d . . .
H20 H 0.0372 0.1357 -0.0188 0.040 Uiso 1 1 calc R A .
C21 C 0.2267(2) 0.12767(16) 0.03549(16) 0.0320(4) Uani 1 1 d . A .
C22 C 0.3572(2) 0.19361(16) 0.11702(16) 0.0325(4) Uani 1 1 d . . .
H22 H 0.4278 0.1606 0.1155 0.039 Uiso 1 1 calc R A .
C23 C 0.38666(19) 0.30694(16) 0.20077(15) 0.0283(4) Uani 1 1 d . A .
H23 H 0.4772 0.3513 0.2549 0.034 Uiso 1 1 calc R . .
C24 C 0.1967(2) 0.00236(17) -0.05126(19) 0.0483(6) Uani 1 1 d . . .
H24A H 0.1028 -0.0294 -0.1059 0.072 Uiso 1 1 calc R A .
H24B H 0.2045 -0.0487 -0.0101 0.072 Uiso 1 1 calc R . .
H24C H 0.2636 0.0040 -0.0940 0.072 Uiso 1 1 calc R . .
C25 C 0.42455(17) 0.57660(15) 0.19986(13) 0.0219(4) Uani 1 1 d . . .
H25A H 0.3999 0.6405 0.1841 0.026 Uiso 1 1 calc R . .
H25B H 0.3652 0.4997 0.1334 0.026 Uiso 1 1 calc R . .
C26 C 0.57406(17) 0.59683(14) 0.20626(13) 0.0196(3) Uani 1 1 d . . .
C27 C 0.62169(17) 0.62665(15) 0.12249(14) 0.0226(4) Uani 1 1 d . . .
H27 H 0.5601 0.6347 0.0637 0.027 Uiso 1 1 calc R . .
C28 C 0.75618(18) 0.64440(16) 0.12433(14) 0.0263(4) Uani 1 1 d . . .
H28 H 0.7870 0.6641 0.0668 0.032 Uiso 1 1 calc R . .
C29 C 0.84764(17) 0.63346(15) 0.21073(15) 0.0246(4) Uani 1 1 d . . .
C30 C 0.80320(17) 0.60505(15) 0.29472(14) 0.0242(4) Uani 1 1 d . . .
H30 H 0.8654 0.5983 0.3542 0.029 Uiso 1 1 calc R . .
C31 C 0.66662(17) 0.58643(15) 0.29114(13) 0.0225(4) Uani 1 1 d . . .
H31 H 0.6359 0.5660 0.3484 0.027 Uiso 1 1 calc R . .
C32 C 1.0751(2) 0.6405(2) 0.2895(2) 0.0534(6) Uani 1 1 d . . .
H32A H 1.0877 0.6986 0.3671 0.080 Uiso 1 1 calc R . .
H32B H 1.1642 0.6544 0.2749 0.080 Uiso 1 1 calc R . .
H32C H 1.0392 0.5595 0.2851 0.080 Uiso 1 1 calc R . .
C33 C 0.58136(17) 1.00845(15) 0.71424(14) 0.0229(4) Uani 1 1 d . . .
C34 C 0.49568(19) 1.03249(16) 0.78173(15) 0.0276(4) Uani 1 1 d . . .
H34 H 0.4035 0.9779 0.7571 0.033 Uiso 1 1 calc R . .
C35 C 0.54351(19) 1.13489(16) 0.88401(15) 0.0301(4) Uani 1 1 d . . .
H35 H 0.4827 1.1499 0.9276 0.036 Uiso 1 1 calc R . .
C36 C 0.67800(19) 1.21582(15) 0.92420(14) 0.0277(4) Uani 1 1 d . . .
C37 C 0.7629(2) 1.19267(16) 0.85723(16) 0.0313(4) Uani 1 1 d . . .
H37 H 0.8551 1.2475 0.8824 0.038 Uiso 1 1 calc R . .
C38 C 0.71585(19) 1.09079(16) 0.75380(15) 0.0297(4) Uani 1 1 d . . .
H38 H 0.7763 1.0772 0.7095 0.036 Uiso 1 1 calc R . .
C39 C 0.7293(2) 1.32339(17) 1.03947(16) 0.0365(5) Uani 1 1 d . . .
H39A H 0.6576 1.3597 1.0449 0.044 Uiso 1 1 calc R . .
H39B H 0.8134 1.3835 1.0429 0.044 Uiso 1 1 calc R . .
C40 C 0.7629(2) 1.29171(18) 1.14213(16) 0.0392(5) Uani 1 1 d . . .
H40A H 0.6815 1.2291 1.1369 0.059 Uiso 1 1 calc R . .
H40B H 0.7889 1.3627 1.2145 0.059 Uiso 1 1 calc R . .
H40C H 0.8401 1.2629 1.1413 0.059 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C9 1.381(2) . ?
N1 C1 1.399(2) . ?
N1 C25 1.4732(19) . ?
O1 C7 1.2441(18) . ?
O2 C29 1.372(2) . ?
O2 C32 1.421(2) . ?
C1 C6 1.404(2) . ?
C1 C2 1.407(2) . ?
C2 C3 1.372(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(2) . ?
C4 C33 1.488(2) . ?
C5 C6 1.403(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.459(2) . ?
C7 C8 1.449(2) . ?
C8 C9 1.370(2) . ?
C8 C10 1.506(3) . ?
C8 Br1 1.874(9) . ?
C9 C18 1.494(2) . ?
C10 C11 1.377(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C16 1.503(3) . ?
C14 C15 1.410(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.389(2) . ?
C18 C23 1.391(2) . ?
C19 C20 1.395(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 C24 1.513(3) . ?
C22 C23 1.388(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.512(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C31 1.384(2) . ?
C26 C27 1.402(2) . ?
C27 C28 1.373(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.395(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(2) . ?
C30 C31 1.388(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C38 1.393(2) . ?
C33 C34 1.398(2) . ?
C34 C35 1.386(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.384(3) . ?
C36 C39 1.514(2) . ?
C37 C38 1.391(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.517(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
C9 N1 C1 120.08(13) . . ?
C9 N1 C25 121.16(13) . . ?
C1 N1 C25 118.49(13) . . ?
C29 O2 C32 116.97(15) . . ?
N1 C1 C6 119.46(14) . . ?
N1 C1 C2 121.82(14) . . ?
C6 C1 C2 118.72(14) . . ?
C3 C2 C1 120.14(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 122.08(16) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 117.29(14) . . ?
C5 C4 C33 120.58(14) . . ?
C3 C4 C33 122.13(15) . . ?
C4 C5 C6 122.21(14) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 119.49(15) . . ?
C5 C6 C7 119.10(14) . . ?
C1 C6 C7 121.41(14) . . ?
O1 C7 C8 123.08(15) . . ?
O1 C7 C6 121.25(14) . . ?
C8 C7 C6 115.66(13) . . ?
C9 C8 C7 120.63(15) . . ?
C9 C8 C10 122.95(15) . . ?
C7 C8 C10 116.39(14) . . ?
C9 C8 Br1 114.5(2) . . ?
C7 C8 Br1 123.0(2) . . ?
C10 C8 Br1 16.9(2) . . ?
C8 C9 N1 122.53(14) . . ?
C8 C9 C18 119.80(14) . . ?
N1 C9 C18 117.61(13) . . ?
C11 C10 C15 119.40(19) . . ?
C11 C10 C8 119.4(2) . . ?
C15 C10 C8 121.05(18) . . ?
C10 C11 C12 120.91(18) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 121.40(17) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 117.43(16) . . ?
C12 C13 C16 121.07(17) . . ?
C14 C13 C16 121.43(17) . . ?
C13 C14 C15 121.63(18) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C14 119.20(17) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C13 C16 C17 115.13(17) . . ?
C13 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C13 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C19 C18 C23 119.09(16) . . ?
C19 C18 C9 121.39(15) . . ?
C23 C18 C9 119.21(14) . . ?
C18 C19 C20 120.02(17) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.14(17) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 118.31(17) . . ?
C20 C21 C24 121.88(19) . . ?
C22 C21 C24 119.78(19) . . ?
C21 C22 C23 121.29(18) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C18 120.10(17) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 C26 114.65(13) . . ?
N1 C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
N1 C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C31 C26 C27 118.14(15) . . ?
C31 C26 C25 122.86(14) . . ?
C27 C26 C25 119.00(14) . . ?
C28 C27 C26 120.87(15) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 119.99(15) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
O2 C29 C30 124.69(15) . . ?
O2 C29 C28 115.20(15) . . ?
C30 C29 C28 120.12(16) . . ?
C29 C30 C31 119.21(15) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C26 C31 C30 121.67(15) . . ?
C26 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 117.58(16) . . ?
C38 C33 C4 122.06(15) . . ?
C34 C33 C4 120.35(15) . . ?
C35 C34 C33 120.86(17) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C36 C35 C34 121.50(17) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C37 C36 C35 117.78(16) . . ?
C37 C36 C39 122.01(17) . . ?
C35 C36 C39 120.18(17) . . ?
C36 C37 C38 121.34(17) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C37 C38 C33 120.92(17) . . ?
C37 C38 H38 119.5 . . ?
C33 C38 H38 119.5 . . ?
C36 C39 C40 112.42(16) . . ?
C36 C39 H39A 109.1 . . ?
C40 C39 H39A 109.1 . . ?
C36 C39 H39B 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H39A C39 H39B 107.9 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C6 -1.4(2) . . . . ?
C25 N1 C1 C6 172.67(14) . . . . ?
C9 N1 C1 C2 178.21(15) . . . . ?
C25 N1 C1 C2 -7.7(2) . . . . ?
N1 C1 C2 C3 -176.95(15) . . . . ?
C6 C1 C2 C3 2.7(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 C33 178.71(16) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C33 C4 C5 C6 -178.41(15) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 -179.67(15) . . . . ?
N1 C1 C6 C5 177.27(14) . . . . ?
C2 C1 C6 C5 -2.4(2) . . . . ?
N1 C1 C6 C7 -2.8(2) . . . . ?
C2 C1 C6 C7 177.51(15) . . . . ?
C5 C6 C7 O1 2.3(2) . . . . ?
C1 C6 C7 O1 -177.56(15) . . . . ?
C5 C6 C7 C8 -176.41(15) . . . . ?
C1 C6 C7 C8 3.7(2) . . . . ?
O1 C7 C8 C9 -179.14(15) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
O1 C7 C8 C10 2.4(2) . . . . ?
C6 C7 C8 C10 -178.83(16) . . . . ?
O1 C7 C8 Br1 -15.6(4) . . . . ?
C6 C7 C8 Br1 163.2(3) . . . . ?
C7 C8 C9 N1 -3.9(2) . . . . ?
C10 C8 C9 N1 174.46(17) . . . . ?
Br1 C8 C9 N1 -168.7(3) . . . . ?
C7 C8 C9 C18 173.44(15) . . . . ?
C10 C8 C9 C18 -8.2(3) . . . . ?
Br1 C8 C9 C18 8.6(3) . . . . ?
C1 N1 C9 C8 4.9(2) . . . . ?
C25 N1 C9 C8 -169.08(15) . . . . ?
C1 N1 C9 C18 -172.48(14) . . . . ?
C25 N1 C9 C18 13.6(2) . . . . ?
C9 C8 C10 C11 -116.16(19) . . . . ?
C7 C8 C10 C11 62.2(2) . . . . ?
Br1 C8 C10 C11 179.3(8) . . . . ?
C9 C8 C10 C15 68.6(2) . . . . ?
C7 C8 C10 C15 -113.02(19) . . . . ?
Br1 C8 C10 C15 4.1(7) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C8 C10 C11 C12 -176.37(15) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C11 C12 C13 C14 -1.9(2) . . . . ?
C11 C12 C13 C16 174.94(16) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C16 C13 C14 C15 -175.65(17) . . . . ?
C11 C10 C15 C14 0.3(2) . . . . ?
C8 C10 C15 C14 175.57(15) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C12 C13 C16 C17 125.1(2) . . . . ?
C14 C13 C16 C17 -58.2(2) . . . . ?
C8 C9 C18 C19 73.1(2) . . . . ?
N1 C9 C18 C19 -109.47(18) . . . . ?
C8 C9 C18 C23 -100.47(19) . . . . ?
N1 C9 C18 C23 77.0(2) . . . . ?
C23 C18 C19 C20 0.6(2) . . . . ?
C9 C18 C19 C20 -173.03(15) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C19 C20 C21 C22 -2.4(3) . . . . ?
C19 C20 C21 C24 175.93(18) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C24 C21 C22 C23 -177.39(17) . . . . ?
C21 C22 C23 C18 1.2(3) . . . . ?
C19 C18 C23 C22 -2.0(2) . . . . ?
C9 C18 C23 C22 171.76(16) . . . . ?
C9 N1 C25 C26 -111.04(16) . . . . ?
C1 N1 C25 C26 74.91(18) . . . . ?
N1 C25 C26 C31 14.5(2) . . . . ?
N1 C25 C26 C27 -165.98(14) . . . . ?
C31 C26 C27 C28 0.3(2) . . . . ?
C25 C26 C27 C28 -179.24(15) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C32 O2 C29 C30 2.0(3) . . . . ?
C32 O2 C29 C28 -178.51(18) . . . . ?
C27 C28 C29 O2 -179.70(15) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
O2 C29 C30 C31 -179.83(16) . . . . ?
C28 C29 C30 C31 0.7(3) . . . . ?
C27 C26 C31 C30 0.2(2) . . . . ?
C25 C26 C31 C30 179.75(15) . . . . ?
C29 C30 C31 C26 -0.7(3) . . . . ?
C5 C4 C33 C38 142.45(18) . . . . ?
C3 C4 C33 C38 -37.6(2) . . . . ?
C5 C4 C33 C34 -36.1(2) . . . . ?
C3 C4 C33 C34 143.93(17) . . . . ?
C38 C33 C34 C35 0.2(3) . . . . ?
C4 C33 C34 C35 178.73(16) . . . . ?
C33 C34 C35 C36 -1.2(3) . . . . ?
C34 C35 C36 C37 1.5(3) . . . . ?
C34 C35 C36 C39 -176.72(17) . . . . ?
C35 C36 C37 C38 -0.9(3) . . . . ?
C39 C36 C37 C38 177.29(17) . . . . ?
C36 C37 C38 C33 0.0(3) . . . . ?
C34 C33 C38 C37 0.4(3) . . . . ?
C4 C33 C38 C37 -178.11(17) . . . . ?
C37 C36 C39 C40 -101.3(2) . . . . ?
C35 C36 C39 C40 76.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_is_mm115_118
_database_code_depnum_ccdc_archive 'CCDC 1403824'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
(R)-6-Nitro-1-(1-phenylethyl)-2-(4-tolyl)quinolin-4(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O3'
_chemical_formula_sum            'C24 H20 N2 O3'
_chemical_formula_weight         384.42

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.9322(10)
_cell_length_b                   13.6154(10)
_cell_length_c                   14.4052(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1948.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3063
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15463
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.628
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5004
_reflns_number_gt                3347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.976

_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.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0048(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1083 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5004
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.3487(2) 0.24717(15) 0.79814(15) 0.0236(5) Uani 1 1 d . . . . .
N2 N 0.2433(2) 0.57140(16) 0.56720(17) 0.0307(6) Uani 1 1 d . . . . .
C6 C 0.1906(3) 0.36422(18) 0.73286(19) 0.0246(6) Uani 1 1 d . . . . .
C4 C 0.2696(3) 0.48692(17) 0.62718(19) 0.0250(6) Uani 1 1 d . . . . .
C1 C 0.3231(3) 0.32716(17) 0.74065(18) 0.0224(6) Uani 1 1 d . . . . .
C9 C 0.2418(3) 0.20009(17) 0.84153(19) 0.0254(6) Uani 1 1 d . . . . .
C5 C 0.1662(3) 0.44525(18) 0.67556(18) 0.0268(6) Uani 1 1 d . . . . .
H5 H 0.0778 0.4712 0.6703 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0780(3) 0.3200(2) 0.7833(2) 0.0285(6) Uani 1 1 d . . . . .
C3 C 0.4010(3) 0.45059(18) 0.63279(19) 0.0270(6) Uani 1 1 d . . . . .
H3 H 0.4713 0.4802 0.5980 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4271(3) 0.37197(18) 0.68895(19) 0.0263(6) Uani 1 1 d . . . . .
H2 H 0.5162 0.3472 0.6933 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5766(3) 0.18427(17) 0.74754(19) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.2663(3) 0.10828(18) 0.89616(18) 0.0251(6) Uani 1 1 d . . . . .
C23 C 0.7131(3) 0.20639(18) 0.7427(2) 0.0271(6) Uani 1 1 d . . . . .
H23 H 0.7510 0.2519 0.7853 0.033 Uiso 1 1 calc R U . . .
C17 C 0.4900(2) 0.22359(18) 0.82591(18) 0.0238(6) Uani 1 1 d . . . . .
H17 H 0.4819 0.1679 0.8708 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3201(3) 0.10910(19) 0.98555(19) 0.0282(6) Uani 1 1 d . . . . .
H15 H 0.3486 0.1694 1.0123 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2227(3) 0.01931(18) 0.8591(2) 0.0315(7) Uani 1 1 d . . . . .
H11 H 0.1845 0.0174 0.7987 0.038 Uiso 1 1 calc R U . . .
C22 C 0.7942(3) 0.1628(2) 0.6764(2) 0.0377(7) Uani 1 1 d . . . . .
H22 H 0.8875 0.1781 0.6743 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2349(3) -0.0667(2) 0.9105(2) 0.0364(7) Uani 1 1 d . . . . .
H12 H 0.2042 -0.1268 0.8846 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5233(3) 0.11851(19) 0.6833(2) 0.0352(7) Uani 1 1 d . . . . .
H19 H 0.4301 0.1030 0.6851 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1133(3) 0.23275(19) 0.8335(2) 0.0305(7) Uani 1 1 d . . . . .
H8 H 0.0435 0.1961 0.8624 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3322(3) 0.02267(19) 1.0358(2) 0.0340(7) Uani 1 1 d . . . . .
H14 H 0.3693 0.0245 1.0965 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2910(3) -0.0667(2) 0.9984(2) 0.0355(7) Uani 1 1 d . . . . .
C16 C 0.3097(4) -0.1617(2) 1.0518(3) 0.0539(9) Uani 1 1 d . . . . .
H16A H 0.3327 -0.1467 1.1164 0.081 Uiso 1 1 calc R U . . .
H16B H 0.3824 -0.2000 1.0235 0.081 Uiso 1 1 calc R U . . .
H16C H 0.2259 -0.1997 1.0500 0.081 Uiso 1 1 calc R U . . .
C21 C 0.7408(4) 0.0977(2) 0.6138(2) 0.0489(9) Uani 1 1 d . . . . .
H21 H 0.7969 0.0678 0.5685 0.059 Uiso 1 1 calc R U . . .
C20 C 0.6048(4) 0.0757(2) 0.6170(2) 0.0469(9) Uani 1 1 d . . . . .
H20 H 0.5674 0.0310 0.5734 0.056 Uiso 1 1 calc R U . . .
C24 C 0.5504(3) 0.30807(19) 0.8821(2) 0.0320(7) Uani 1 1 d . . . . .
H24A H 0.4853 0.3299 0.9289 0.048 Uiso 1 1 calc R U . . .
H24B H 0.5718 0.3628 0.8405 0.048 Uiso 1 1 calc R U . . .
H24C H 0.6328 0.2857 0.9130 0.048 Uiso 1 1 calc R U . . .
O1 O 0.3359(2) 0.60525(13) 0.52142(15) 0.0418(5) Uani 1 1 d . . . . .
O2 O 0.1281(2) 0.60449(14) 0.56534(15) 0.0449(6) Uani 1 1 d . . . . .
O3 O -0.03701(19) 0.35565(14) 0.78101(16) 0.0409(6) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
N1 C9 1.389(3) . ?
N1 C1 1.392(3) . ?
N1 C17 1.494(3) . ?
N2 O1 1.222(3) . ?
N2 O2 1.230(3) . ?
N2 C4 1.462(3) . ?
C6 C5 1.399(3) . ?
C6 C1 1.414(3) . ?
C6 C7 1.464(4) . ?
C4 C5 1.364(4) . ?
C4 C3 1.398(3) . ?
C1 C2 1.412(3) . ?
C9 C8 1.357(3) . ?
C9 C10 1.497(4) . ?
C5 H5 0.9500 . ?
C7 O3 1.241(3) . ?
C7 C8 1.433(4) . ?
C3 C2 1.367(3) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C18 C23 1.390(3) . ?
C18 C19 1.392(4) . ?
C18 C17 1.517(4) . ?
C10 C11 1.393(4) . ?
C10 C15 1.394(4) . ?
C23 C22 1.383(4) . ?
C23 H23 0.9500 . ?
C17 C24 1.529(4) . ?
C17 H17 1.0000 . ?
C15 C14 1.387(4) . ?
C15 H15 0.9500 . ?
C11 C12 1.390(4) . ?
C11 H11 0.9500 . ?
C22 C21 1.372(4) . ?
C22 H22 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C14 C13 1.392(4) . ?
C14 H14 0.9500 . ?
C13 C16 1.516(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C21 C20 1.384(4) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C9 N1 C1 119.3(2) . . ?
C9 N1 C17 119.9(2) . . ?
C1 N1 C17 120.0(2) . . ?
O1 N2 O2 123.4(2) . . ?
O1 N2 C4 118.8(2) . . ?
O2 N2 C4 117.9(2) . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 119.0(2) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 N2 119.6(2) . . ?
C3 C4 N2 118.6(2) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 119.8(2) . . ?
C2 C1 C6 119.0(2) . . ?
C8 C9 N1 122.0(2) . . ?
C8 C9 C10 118.2(2) . . ?
N1 C9 C10 119.8(2) . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O3 C7 C8 124.3(3) . . ?
O3 C7 C6 121.9(3) . . ?
C8 C7 C6 113.8(2) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C23 C18 C19 118.5(3) . . ?
C23 C18 C17 120.9(2) . . ?
C19 C18 C17 120.4(2) . . ?
C11 C10 C15 118.7(2) . . ?
C11 C10 C9 118.3(2) . . ?
C15 C10 C9 122.8(2) . . ?
C22 C23 C18 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
N1 C17 C18 114.1(2) . . ?
N1 C17 C24 110.38(19) . . ?
C18 C17 C24 115.9(2) . . ?
N1 C17 H17 105.1 . . ?
C18 C17 H17 105.1 . . ?
C24 C17 H17 105.1 . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C9 C8 C7 123.0(2) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 C16 120.9(3) . . ?
C14 C13 C16 120.9(3) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C4 C5 -177.0(2) . . . . ?
O2 N2 C4 C5 2.7(4) . . . . ?
O1 N2 C4 C3 2.6(4) . . . . ?
O2 N2 C4 C3 -177.7(2) . . . . ?
C9 N1 C1 C2 -174.5(2) . . . . ?
C17 N1 C1 C2 16.2(3) . . . . ?
C9 N1 C1 C6 5.0(3) . . . . ?
C17 N1 C1 C6 -164.4(2) . . . . ?
C5 C6 C1 N1 179.4(2) . . . . ?
C7 C6 C1 N1 -0.6(4) . . . . ?
C5 C6 C1 C2 -1.1(4) . . . . ?
C7 C6 C1 C2 178.9(2) . . . . ?
C1 N1 C9 C8 -3.5(4) . . . . ?
C17 N1 C9 C8 165.9(2) . . . . ?
C1 N1 C9 C10 174.2(2) . . . . ?
C17 N1 C9 C10 -16.5(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
N2 C4 C5 C6 179.8(2) . . . . ?
C1 C6 C5 C4 0.7(4) . . . . ?
C7 C6 C5 C4 -179.3(2) . . . . ?
C5 C6 C7 O3 -4.3(4) . . . . ?
C1 C6 C7 O3 175.7(3) . . . . ?
C5 C6 C7 C8 175.1(2) . . . . ?
C1 C6 C7 C8 -5.0(4) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?
N2 C4 C3 C2 179.7(2) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
N1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C8 C9 C10 C11 70.1(3) . . . . ?
N1 C9 C10 C11 -107.6(3) . . . . ?
C8 C9 C10 C15 -104.2(3) . . . . ?
N1 C9 C10 C15 78.1(3) . . . . ?
C19 C18 C23 C22 -1.0(4) . . . . ?
C17 C18 C23 C22 173.7(2) . . . . ?
C9 N1 C17 C18 120.5(2) . . . . ?
C1 N1 C17 C18 -70.2(3) . . . . ?
C9 N1 C17 C24 -106.8(3) . . . . ?
C1 N1 C17 C24 62.4(3) . . . . ?
C23 C18 C17 N1 145.6(2) . . . . ?
C19 C18 C17 N1 -39.9(3) . . . . ?
C23 C18 C17 C24 15.6(4) . . . . ?
C19 C18 C17 C24 -169.9(2) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C9 C10 C15 C14 175.5(2) . . . . ?
C15 C10 C11 C12 -1.0(4) . . . . ?
C9 C10 C11 C12 -175.5(2) . . . . ?
C18 C23 C22 C21 0.6(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C23 C18 C19 C20 0.6(4) . . . . ?
C17 C18 C19 C20 -174.1(3) . . . . ?
N1 C9 C8 C7 -2.7(4) . . . . ?
C10 C9 C8 C7 179.6(2) . . . . ?
O3 C7 C8 C9 -174.1(3) . . . . ?
C6 C7 C8 C9 6.6(4) . . . . ?
C10 C15 C14 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 1.6(4) . . . . ?
C11 C12 C13 C16 -177.1(3) . . . . ?
C15 C14 C13 C12 -1.3(4) . . . . ?
C15 C14 C13 C16 177.4(3) . . . . ?
C23 C22 C21 C20 0.1(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C22 C21 C20 C19 -0.5(5) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

