# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_SPA102
_database_code_depnum_ccdc_archive 'CCDC 1485284'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-(diphenylamino)-2-propoxybenzaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 N O2'
_chemical_formula_sum            'C22 H21 N O2'
_chemical_formula_weight         331.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.106(2)
_cell_length_b                   14.511(3)
_cell_length_c                   12.224(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.64(3)
_cell_angle_gamma                90
_cell_volume                     1767.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    54701
_cell_measurement_theta_min      0.349
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17397
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.885
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4897
_reflns_number_gt                3905
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL ADSC Quantum-210 ADX Program(Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND(Putz, Brandenburg, 2007)'
_computing_publication_material  'enCIFer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²+0.4054P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4897
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38815(9) 0.34548(6) 0.77808(8) 0.0174(2) Uani 1 1 d . . . . .
O2 O 0.12422(8) 0.54963(6) 0.71692(8) 0.0161(2) Uani 1 1 d . . . . .
N1 N 0.43229(10) 0.74175(7) 0.55283(9) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.30621(12) 0.40654(8) 0.74993(10) 0.0134(2) Uani 1 1 d . . . . .
H1 H 0.2169 0.3971 0.7624 0.016 Uiso 1 1 calc R U . . .
C2 C 0.01367(12) 0.61097(8) 0.68058(11) 0.0153(2) Uani 1 1 d . . . . .
H2A H 0.0033 0.6212 0.5995 0.018 Uiso 1 1 calc R U . . .
H2B H 0.0292 0.6712 0.7185 0.018 Uiso 1 1 calc R U . . .
C3 C -0.11014(12) 0.56564(9) 0.70954(12) 0.0201(3) Uani 1 1 d . . . . .
H3A H -0.1856 0.6100 0.6966 0.024 Uiso 1 1 calc R U . . .
H3B H -0.0939 0.5497 0.7894 0.024 Uiso 1 1 calc R U . . .
C4 C -0.14958(16) 0.47907(11) 0.64226(17) 0.0354(4) Uani 1 1 d . . . . .
H4A H -0.1758 0.4954 0.5638 0.053 Uiso 1 1 calc R U . . .
H4B H -0.2252 0.4493 0.6689 0.053 Uiso 1 1 calc R U . . .
H4C H -0.0732 0.4366 0.6506 0.053 Uiso 1 1 calc R U . . .
C5 C 0.39782(11) 0.65956(8) 0.59969(10) 0.0112(2) Uani 1 1 d . . . . .
C6 C 0.27391(11) 0.64912(8) 0.63615(10) 0.0118(2) Uani 1 1 d . . . . .
H6 H 0.2116 0.6986 0.6292 0.014 Uiso 1 1 calc R U . . .
C7 C 0.24309(11) 0.56599(8) 0.68236(10) 0.0113(2) Uani 1 1 d . . . . .
C8 C 0.33651(11) 0.49301(8) 0.69850(10) 0.0116(2) Uani 1 1 d . . . . .
C9 C 0.45924(12) 0.50533(8) 0.66183(10) 0.0133(2) Uani 1 1 d . . . . .
H9 H 0.5231 0.4567 0.6715 0.016 Uiso 1 1 calc R U . . .
C10 C 0.49016(12) 0.58583(8) 0.61214(10) 0.0131(2) Uani 1 1 d . . . . .
H10 H 0.5733 0.5917 0.5863 0.016 Uiso 1 1 calc R U . . .
C11 C 0.57148(11) 0.76099(8) 0.55107(10) 0.0129(2) Uani 1 1 d . . . . .
C12 C 0.62033(13) 0.75702(9) 0.45196(11) 0.0178(3) Uani 1 1 d . . . . .
H12 H 0.5621 0.7417 0.3851 0.021 Uiso 1 1 calc R U . . .
C13 C 0.75552(13) 0.77568(9) 0.45057(12) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.7892 0.7733 0.3826 0.024 Uiso 1 1 calc R U . . .
C14 C 0.84068(12) 0.79766(8) 0.54786(12) 0.0185(3) Uani 1 1 d . . . . .
H14 H 0.9327 0.8101 0.5467 0.022 Uiso 1 1 calc R U . . .
C15 C 0.79165(12) 0.80144(9) 0.64700(11) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.8502 0.8165 0.7138 0.021 Uiso 1 1 calc R U . . .
C16 C 0.65667(12) 0.78323(8) 0.64899(10) 0.0153(2) Uani 1 1 d . . . . .
H16 H 0.6230 0.7860 0.7170 0.018 Uiso 1 1 calc R U . . .
C17 C 0.33850(12) 0.81188(8) 0.51143(10) 0.0120(2) Uani 1 1 d . . . . .
C18 C 0.37101(12) 0.90405(8) 0.53441(11) 0.0149(2) Uani 1 1 d . . . . .
H18 H 0.4550 0.9196 0.5779 0.018 Uiso 1 1 calc R U . . .
C19 C 0.28095(13) 0.97330(9) 0.49387(11) 0.0183(3) Uani 1 1 d . . . . .
H19 H 0.3037 1.0359 0.5101 0.022 Uiso 1 1 calc R U . . .
C20 C 0.15806(13) 0.95174(9) 0.42995(11) 0.0186(3) Uani 1 1 d . . . . .
H20 H 0.0961 0.9991 0.4034 0.022 Uiso 1 1 calc R U . . .
C21 C 0.12656(12) 0.85987(9) 0.40525(11) 0.0173(3) Uani 1 1 d . . . . .
H21 H 0.0432 0.8447 0.3606 0.021 Uiso 1 1 calc R U . . .
C22 C 0.21600(12) 0.79002(9) 0.44533(10) 0.0149(2) Uani 1 1 d . . . . .
H22 H 0.1938 0.7275 0.4277 0.018 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2221(14) . ?
O2 C7 1.3594(14) . ?
O2 C2 1.4394(14) . ?
N1 C5 1.3923(15) . ?
N1 C17 1.4246(15) . ?
N1 C11 1.4377(15) . ?
C1 C8 1.4589(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.5073(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.4060(16) . ?
C5 C10 1.4110(16) . ?
C6 C7 1.3893(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4104(15) . ?
C8 C9 1.3991(16) . ?
C9 C10 1.3765(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.3839(18) . ?
C11 C16 1.3903(17) . ?
C12 C13 1.3957(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3936(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.3947(16) . ?
C17 C22 1.3968(17) . ?
C18 C19 1.3901(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3877(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3920(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.3914(17) . ?
C21 H21 0.9500 . ?
C22 H22 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
C7 O2 C2 118.47(9) . . ?
C5 N1 C17 124.10(10) . . ?
C5 N1 C11 119.03(10) . . ?
C17 N1 C11 116.77(9) . . ?
O1 C1 C8 124.31(11) . . ?
O1 C1 H1 117.8 . . ?
C8 C1 H1 117.8 . . ?
O2 C2 C3 106.83(10) . . ?
O2 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
O2 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 112.76(12) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 121.34(10) . . ?
N1 C5 C10 119.17(10) . . ?
C6 C5 C10 119.48(10) . . ?
C7 C6 C5 119.65(10) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O2 C7 C6 123.23(10) . . ?
O2 C7 C8 115.53(10) . . ?
C6 C7 C8 121.23(10) . . ?
C9 C8 C7 117.89(10) . . ?
C9 C8 C1 120.62(10) . . ?
C7 C8 C1 121.48(10) . . ?
C10 C9 C8 121.92(11) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C5 119.75(11) . . ?
C9 C10 H10 120.1 . . ?
C5 C10 H10 120.1 . . ?
C12 C11 C16 120.20(11) . . ?
C12 C11 N1 119.90(11) . . ?
C16 C11 N1 119.90(11) . . ?
C11 C12 C13 119.74(12) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.23(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.94(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.16(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.72(12) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C22 119.36(11) . . ?
C18 C17 N1 119.55(11) . . ?
C22 C17 N1 121.05(11) . . ?
C19 C18 C17 120.22(11) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.57(12) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.25(12) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.65(12) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C17 119.93(12) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?

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
C7 O2 C2 C3 167.90(11) . . . . ?
O2 C2 C3 C4 -67.57(15) . . . . ?
C17 N1 C5 C6 -16.82(18) . . . . ?
C11 N1 C5 C6 159.36(11) . . . . ?
C17 N1 C5 C10 164.09(11) . . . . ?
C11 N1 C5 C10 -19.73(16) . . . . ?
N1 C5 C6 C7 179.93(11) . . . . ?
C10 C5 C6 C7 -0.99(17) . . . . ?
C2 O2 C7 C6 15.56(17) . . . . ?
C2 O2 C7 C8 -165.76(10) . . . . ?
C5 C6 C7 O2 -178.25(11) . . . . ?
C5 C6 C7 C8 3.14(17) . . . . ?
O2 C7 C8 C9 178.41(11) . . . . ?
C6 C7 C8 C9 -2.88(17) . . . . ?
O2 C7 C8 C1 -0.52(16) . . . . ?
C6 C7 C8 C1 178.19(11) . . . . ?
O1 C1 C8 C9 10.25(19) . . . . ?
O1 C1 C8 C7 -170.84(12) . . . . ?
C7 C8 C9 C10 0.48(18) . . . . ?
C1 C8 C9 C10 179.42(11) . . . . ?
C8 C9 C10 C5 1.60(18) . . . . ?
N1 C5 C10 C9 177.75(11) . . . . ?
C6 C5 C10 C9 -1.35(17) . . . . ?
C5 N1 C11 C12 107.91(13) . . . . ?
C17 N1 C11 C12 -75.63(15) . . . . ?
C5 N1 C11 C16 -71.88(15) . . . . ?
C17 N1 C11 C16 104.58(13) . . . . ?
C16 C11 C12 C13 -0.17(19) . . . . ?
N1 C11 C12 C13 -179.96(11) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C16 -0.05(19) . . . . ?
C12 C11 C16 C15 -0.07(18) . . . . ?
N1 C11 C16 C15 179.72(10) . . . . ?
C14 C15 C16 C11 0.18(18) . . . . ?
C5 N1 C17 C18 137.24(12) . . . . ?
C11 N1 C17 C18 -39.02(16) . . . . ?
C5 N1 C17 C22 -44.70(17) . . . . ?
C11 N1 C17 C22 139.04(12) . . . . ?
C22 C17 C18 C19 1.42(19) . . . . ?
N1 C17 C18 C19 179.51(11) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C21 -1.0(2) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C17 0.28(19) . . . . ?
C18 C17 C22 C21 -1.46(18) . . . . ?
N1 C17 C22 C21 -179.52(11) . . . . ?

_refine_diff_density_max         1.169
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_SPA104
_database_code_depnum_ccdc_archive 'CCDC 1485286'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-(diphenylamino)-2-ppentyloxybenzaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H25 N O2'
_chemical_formula_sum            'C24 H25 N O2'
_chemical_formula_weight         359.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.937(2)
_cell_length_b                   9.974(2)
_cell_length_c                   19.734(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.93(3)
_cell_angle_gamma                90
_cell_volume                     1953.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    60628
_cell_measurement_theta_min      0.349
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.057
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19199
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5365
_reflns_number_gt                3833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL ADSC Quantum-210 ADX Program(Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND(Putz, Brandenburg, 2007)'
_computing_publication_material  'enCIFer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5365
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29106(10) 0.42023(11) 0.31502(5) 0.0243(2) Uani 1 1 d . . . . .
O2 O 0.62720(9) 0.62416(10) 0.36516(5) 0.0166(2) Uani 1 1 d . . . . .
N1 N 0.85363(11) 0.46155(11) 0.16965(5) 0.0140(2) Uani 1 1 d . . . . .
C1 C 0.39495(13) 0.48286(14) 0.32872(7) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.3990 0.5366 0.3685 0.022 Uiso 1 1 calc R U . . .
C2A C 0.7542(2) 0.6546(3) 0.40001(12) 0.0172(5) Uani 0.749(4) 1 d . . P A 1
H2A1 H 0.8004 0.7278 0.3765 0.021 Uiso 0.749(4) 1 calc R U P A 1
H2A2 H 0.8133 0.5746 0.4015 0.021 Uiso 0.749(4) 1 calc R U P A 1
C3A C 0.72268(19) 0.6974(2) 0.47133(10) 0.0197(5) Uani 0.749(4) 1 d . . P A 1
H3A1 H 0.6668 0.6273 0.4917 0.024 Uiso 0.749(4) 1 calc R U P A 1
H3A2 H 0.8081 0.7041 0.4993 0.024 Uiso 0.749(4) 1 calc R U P A 1
C4A C 0.6493(2) 0.8300(2) 0.47376(10) 0.0212(5) Uani 0.749(4) 1 d . . P A 1
H4A1 H 0.5678 0.8259 0.4429 0.025 Uiso 0.749(4) 1 calc R U P A 1
H4A2 H 0.7083 0.9014 0.4570 0.025 Uiso 0.749(4) 1 calc R U P A 1
C5A C 0.6078(3) 0.8671(3) 0.54494(13) 0.0244(6) Uani 0.749(4) 1 d . . P A 1
H5A1 H 0.6846 0.8499 0.5777 0.029 Uiso 0.749(4) 1 calc R U P A 1
H5A2 H 0.5879 0.9643 0.5461 0.029 Uiso 0.749(4) 1 calc R U P A 1
C6A C 0.4867(4) 0.7913(4) 0.56739(19) 0.0398(8) Uani 0.749(4) 1 d . . P A 1
H6A1 H 0.4069 0.8178 0.5393 0.060 Uiso 0.749(4) 1 calc R U P A 1
H6A2 H 0.4725 0.8119 0.6151 0.060 Uiso 0.749(4) 1 calc R U P A 1
H6A3 H 0.5019 0.6948 0.5624 0.060 Uiso 0.749(4) 1 calc R U P A 1
C2B C 0.7384(8) 0.7142(10) 0.3837(4) 0.0240(16) Uani 0.251(4) 1 d . . P A 2
H2B1 H 0.7595 0.7708 0.3444 0.029 Uiso 0.251(4) 1 calc R U P A 2
H2B2 H 0.8198 0.6617 0.3976 0.029 Uiso 0.251(4) 1 calc R U P A 2
C3B C 0.6974(7) 0.8006(7) 0.4414(3) 0.0281(18) Uani 0.251(4) 1 d . . P A 2
H3B1 H 0.6110 0.8446 0.4277 0.034 Uiso 0.251(4) 1 calc R U P A 2
H3B2 H 0.7657 0.8721 0.4487 0.034 Uiso 0.251(4) 1 calc R U P A 2
C4B C 0.6810(7) 0.7303(8) 0.5081(3) 0.0331(19) Uani 0.251(4) 1 d . . P A 2
H4B1 H 0.7715 0.7123 0.5295 0.040 Uiso 0.251(4) 1 calc R U P A 2
H4B2 H 0.6367 0.6428 0.4991 0.040 Uiso 0.251(4) 1 calc R U P A 2
C5B C 0.5986(10) 0.8092(10) 0.5582(4) 0.0303(19) Uani 0.251(4) 1 d . . P A 2
H5B1 H 0.6178 0.7736 0.6046 0.036 Uiso 0.251(4) 1 calc R U P A 2
H5B2 H 0.6268 0.9044 0.5580 0.036 Uiso 0.251(4) 1 calc R U P A 2
C6B C 0.4500(12) 0.8008(19) 0.5411(7) 0.082(5) Uani 0.251(4) 1 d . . P A 2
H6B1 H 0.4302 0.8387 0.4959 0.123 Uiso 0.251(4) 1 calc R U P A 2
H6B2 H 0.4014 0.8514 0.5747 0.123 Uiso 0.251(4) 1 calc R U P A 2
H6B3 H 0.4215 0.7068 0.5416 0.123 Uiso 0.251(4) 1 calc R U P A 2
C7 C 0.74016(13) 0.46978(13) 0.20793(6) 0.0125(3) Uani 1 1 d . . . . .
C8 C 0.74213(12) 0.54861(13) 0.26695(6) 0.0124(3) Uani 1 1 d . . . . .
H8 H 0.8202 0.5993 0.2800 0.015 Uiso 1 1 calc R U . . .
C9 C 0.63012(13) 0.55266(12) 0.30637(6) 0.0124(3) Uani 1 1 d . . . . .
C10 C 0.51265(12) 0.48001(13) 0.28773(6) 0.0140(3) Uani 1 1 d . . . . .
C11 C 0.51338(13) 0.40237(13) 0.22863(7) 0.0154(3) Uani 1 1 d . . . . .
H11 H 0.4353 0.3519 0.2155 0.018 Uiso 1 1 calc R U . . .
C12 C 0.62300(13) 0.39643(13) 0.18888(6) 0.0145(3) Uani 1 1 d . . . . .
H12 H 0.6198 0.3433 0.1489 0.017 Uiso 1 1 calc R U . . .
C13 C 0.86603(13) 0.35884(13) 0.11926(6) 0.0132(3) Uani 1 1 d . . . . .
C14 C 0.85859(13) 0.22399(13) 0.13595(7) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.8453 0.1978 0.1814 0.019 Uiso 1 1 calc R U . . .
C15 C 0.87065(13) 0.12724(14) 0.08578(7) 0.0181(3) Uani 1 1 d . . . . .
H15 H 0.8636 0.0349 0.0969 0.022 Uiso 1 1 calc R U . . .
C16 C 0.89289(15) 0.16520(15) 0.01951(7) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.9015 0.0989 -0.0146 0.025 Uiso 1 1 calc R U . . .
C17 C 0.90246(15) 0.29973(15) 0.00328(7) 0.0206(3) Uani 1 1 d . . . . .
H17 H 0.9186 0.3257 -0.0419 0.025 Uiso 1 1 calc R U . . .
C18 C 0.88855(14) 0.39690(14) 0.05283(6) 0.0165(3) Uani 1 1 d . . . . .
H18 H 0.8944 0.4892 0.0415 0.020 Uiso 1 1 calc R U . . .
C19 C 0.96079(13) 0.55711(13) 0.17500(6) 0.0127(3) Uani 1 1 d . . . . .
C20 C 1.09296(13) 0.51002(14) 0.17996(6) 0.0161(3) Uani 1 1 d . . . . .
H20 H 1.1099 0.4165 0.1838 0.019 Uiso 1 1 calc R U . . .
C21 C 1.19946(13) 0.59914(14) 0.17925(7) 0.0175(3) Uani 1 1 d . . . . .
H21 H 1.2894 0.5664 0.1812 0.021 Uiso 1 1 calc R U . . .
C22 C 1.17567(14) 0.73625(14) 0.17565(6) 0.0168(3) Uani 1 1 d . . . . .
H22 H 1.2488 0.7974 0.1744 0.020 Uiso 1 1 calc R U . . .
C23 C 1.04416(14) 0.78278(13) 0.17385(6) 0.0161(3) Uani 1 1 d . . . . .
H23 H 1.0276 0.8766 0.1735 0.019 Uiso 1 1 calc R U . . .
C24 C 0.93624(13) 0.69415(13) 0.17257(6) 0.0143(3) Uani 1 1 d . . . . .
H24 H 0.8464 0.7270 0.1701 0.017 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2249(17) . ?
O2 C9 1.3633(15) . ?
O2 C2A 1.438(2) . ?
O2 C2B 1.456(7) . ?
N1 C7 1.3913(16) . ?
N1 C19 1.4290(16) . ?
N1 C13 1.4373(16) . ?
C1 C10 1.4559(18) . ?
C1 H1 0.9500 . ?
C2A C3A 1.519(3) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.512(3) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.530(3) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.507(4) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9800 . ?
C6A H6A2 0.9800 . ?
C6A H6A3 0.9800 . ?
C2B C3B 1.501(10) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.507(10) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C4B C5B 1.534(11) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5B C6B 1.500(16) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?
C7 C8 1.4047(17) . ?
C7 C12 1.4096(18) . ?
C8 C9 1.3908(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4068(18) . ?
C10 C11 1.4003(18) . ?
C11 C12 1.3757(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3876(19) . ?
C13 C18 1.3938(18) . ?
C14 C15 1.3920(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3886(18) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3888(18) . ?
C19 C20 1.3936(18) . ?
C20 C21 1.3827(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3890(19) . ?
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
C9 O2 C2A 117.45(12) . . ?
C9 O2 C2B 119.2(3) . . ?
C7 N1 C19 122.82(10) . . ?
C7 N1 C13 121.21(11) . . ?
C19 N1 C13 115.89(10) . . ?
O1 C1 C10 124.01(13) . . ?
O1 C1 H1 118.0 . . ?
C10 C1 H1 118.0 . . ?
O2 C2A C3A 106.56(16) . . ?
O2 C2A H2A1 110.4 . . ?
C3A C2A H2A1 110.4 . . ?
O2 C2A H2A2 110.4 . . ?
C3A C2A H2A2 110.4 . . ?
H2A1 C2A H2A2 108.6 . . ?
C4A C3A C2A 113.43(19) . . ?
C4A C3A H3A1 108.9 . . ?
C2A C3A H3A1 108.9 . . ?
C4A C3A H3A2 108.9 . . ?
C2A C3A H3A2 108.9 . . ?
H3A1 C3A H3A2 107.7 . . ?
C3A C4A C5A 113.20(19) . . ?
C3A C4A H4A1 108.9 . . ?
C5A C4A H4A1 108.9 . . ?
C3A C4A H4A2 108.9 . . ?
C5A C4A H4A2 108.9 . . ?
H4A1 C4A H4A2 107.8 . . ?
C6A C5A C4A 113.9(2) . . ?
C6A C5A H5A1 108.8 . . ?
C4A C5A H5A1 108.8 . . ?
C6A C5A H5A2 108.8 . . ?
C4A C5A H5A2 108.8 . . ?
H5A1 C5A H5A2 107.7 . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
O2 C2B C3B 108.2(5) . . ?
O2 C2B H2B1 110.1 . . ?
C3B C2B H2B1 110.1 . . ?
O2 C2B H2B2 110.1 . . ?
C3B C2B H2B2 110.1 . . ?
H2B1 C2B H2B2 108.4 . . ?
C2B C3B C4B 116.2(7) . . ?
C2B C3B H3B1 108.2 . . ?
C4B C3B H3B1 108.2 . . ?
C2B C3B H3B2 108.2 . . ?
C4B C3B H3B2 108.2 . . ?
H3B1 C3B H3B2 107.4 . . ?
C3B C4B C5B 114.2(7) . . ?
C3B C4B H4B1 108.7 . . ?
C5B C4B H4B1 108.7 . . ?
C3B C4B H4B2 108.7 . . ?
C5B C4B H4B2 108.7 . . ?
H4B1 C4B H4B2 107.6 . . ?
C6B C5B C4B 112.2(8) . . ?
C6B C5B H5B1 109.2 . . ?
C4B C5B H5B1 109.2 . . ?
C6B C5B H5B2 109.2 . . ?
C4B C5B H5B2 109.2 . . ?
H5B1 C5B H5B2 107.9 . . ?
C5B C6B H6B1 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C5B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
N1 C7 C8 120.39(12) . . ?
N1 C7 C12 120.39(11) . . ?
C8 C7 C12 119.21(12) . . ?
C9 C8 C7 120.16(12) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O2 C9 C8 122.93(11) . . ?
O2 C9 C10 116.01(11) . . ?
C8 C9 C10 121.05(11) . . ?
C11 C10 C9 117.60(12) . . ?
C11 C10 C1 120.80(12) . . ?
C9 C10 C1 121.60(12) . . ?
C12 C11 C10 122.45(12) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C7 119.53(12) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C14 C13 C18 120.02(12) . . ?
C14 C13 N1 121.28(11) . . ?
C18 C13 N1 118.69(12) . . ?
C13 C14 C15 119.71(12) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.26(13) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.86(13) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.22(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 119.92(13) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C24 C19 C20 119.82(12) . . ?
C24 C19 N1 121.67(11) . . ?
C20 C19 N1 118.45(12) . . ?
C21 C20 C19 120.11(13) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.34(12) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.27(12) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 120.90(13) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C19 C24 C23 119.45(12) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?

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 O2 C2A C3A -164.23(14) . . . . ?
O2 C2A C3A C4A -68.2(2) . . . . ?
C2A C3A C4A C5A 175.32(19) . . . . ?
C3A C4A C5A C6A -76.5(3) . . . . ?
C9 O2 C2B C3B 168.2(4) . . . . ?
O2 C2B C3B C4B 68.0(8) . . . . ?
C2B C3B C4B C5B -161.9(7) . . . . ?
C3B C4B C5B C6B 78.0(12) . . . . ?
C19 N1 C7 C8 -18.45(18) . . . . ?
C13 N1 C7 C8 164.95(12) . . . . ?
C19 N1 C7 C12 163.16(12) . . . . ?
C13 N1 C7 C12 -13.44(18) . . . . ?
N1 C7 C8 C9 -177.67(11) . . . . ?
C12 C7 C8 C9 0.74(19) . . . . ?
C2A O2 C9 C8 -23.2(2) . . . . ?
C2B O2 C9 C8 8.2(5) . . . . ?
C2A O2 C9 C10 155.82(16) . . . . ?
C2B O2 C9 C10 -172.8(5) . . . . ?
C7 C8 C9 O2 178.09(11) . . . . ?
C7 C8 C9 C10 -0.87(19) . . . . ?
O2 C9 C10 C11 -178.24(11) . . . . ?
C8 C9 C10 C11 0.79(19) . . . . ?
O2 C9 C10 C1 0.66(18) . . . . ?
C8 C9 C10 C1 179.69(12) . . . . ?
O1 C1 C10 C11 -0.3(2) . . . . ?
O1 C1 C10 C9 -179.14(13) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C1 C10 C11 C12 -179.53(12) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
N1 C7 C12 C11 177.84(12) . . . . ?
C8 C7 C12 C11 -0.56(19) . . . . ?
C7 N1 C13 C14 -57.28(17) . . . . ?
C19 N1 C13 C14 125.90(13) . . . . ?
C7 N1 C13 C18 123.97(14) . . . . ?
C19 N1 C13 C18 -52.85(16) . . . . ?
C18 C13 C14 C15 -1.5(2) . . . . ?
N1 C13 C14 C15 179.81(12) . . . . ?
C13 C14 C15 C16 1.4(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
N1 C13 C18 C17 179.27(12) . . . . ?
C7 N1 C19 C24 -48.96(17) . . . . ?
C13 N1 C19 C24 127.81(12) . . . . ?
C7 N1 C19 C20 133.71(13) . . . . ?
C13 N1 C19 C20 -49.52(15) . . . . ?
C24 C19 C20 C21 -3.03(18) . . . . ?
N1 C19 C20 C21 174.35(11) . . . . ?
C19 C20 C21 C22 1.93(19) . . . . ?
C20 C21 C22 C23 1.00(19) . . . . ?
C21 C22 C23 C24 -2.87(19) . . . . ?
C20 C19 C24 C23 1.19(18) . . . . ?
N1 C19 C24 C23 -176.10(11) . . . . ?
C22 C23 C24 C19 1.77(19) . . . . ?

_refine_diff_density_max         1.233
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_SPA103
_database_code_depnum_ccdc_archive 'CCDC 1485285'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-(diphenylamino)-2-butyloxybenzaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N O2'
_chemical_formula_sum            'C23 H23 N O2'
_chemical_formula_weight         345.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4190(19)
_cell_length_b                   10.485(2)
_cell_length_c                   19.426(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.60(3)
_cell_angle_gamma                90
_cell_volume                     1917.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    57147
_cell_measurement_theta_min      0.349
_cell_measurement_theta_max      33.679

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.056
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.610
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18585
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.856
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5307
_reflns_number_gt                3965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL ADSC Quantum-210 ADX Program(Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND(Putz, Brandenburg, 2007)'
_computing_publication_material  'enCIFer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+0.1689P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5307
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1523
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26882(11) 0.57699(10) 0.32697(6) 0.0201(2) Uani 1 1 d . . . . .
O2 O 0.60602(10) 0.36017(9) 0.36870(5) 0.0162(2) Uani 1 1 d . . . . .
N1 N 0.86580(12) 0.53389(10) 0.17829(5) 0.0124(2) Uani 1 1 d . . . . .
C1 C 0.37492(14) 0.51279(13) 0.33906(7) 0.0154(3) Uani 1 1 d . . . . .
H1 H 0.3747 0.4571 0.3776 0.018 Uiso 1 1 calc R U . . .
C2 C 0.72545(16) 0.28653(16) 0.39255(7) 0.0216(3) Uani 1 1 d . . . . .
H2A H 0.8005 0.3431 0.4120 0.026 Uiso 1 1 calc R U . . .
H2B H 0.7653 0.2375 0.3541 0.026 Uiso 1 1 calc R U . . .
C3 C 0.67269(18) 0.19639(16) 0.44764(8) 0.0260(4) Uani 1 1 d . . . . .
H3A H 0.5914 0.1469 0.4283 0.031 Uiso 1 1 calc R U . . .
H3B H 0.7493 0.1353 0.4601 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6267(2) 0.26419(18) 0.51226(9) 0.0352(4) Uani 1 1 d . . . . .
H4A H 0.5561 0.3307 0.4995 0.042 Uiso 1 1 calc R U . . .
H4B H 0.7100 0.3069 0.5343 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5616(2) 0.17210(19) 0.56383(9) 0.0372(4) Uani 1 1 d . . . . .
H5A H 0.4760 0.1332 0.5431 0.056 Uiso 1 1 calc R U . . .
H5B H 0.5365 0.2190 0.6054 0.056 Uiso 1 1 calc R U . . .
H5C H 0.6306 0.1053 0.5760 0.056 Uiso 1 1 calc R U . . .
C6 C 0.74475(14) 0.52612(12) 0.21696(6) 0.0110(3) Uani 1 1 d . . . . .
C7 C 0.74089(14) 0.44421(12) 0.27443(6) 0.0116(3) Uani 1 1 d . . . . .
H7 H 0.8209 0.3928 0.2864 0.014 Uiso 1 1 calc R U . . .
C8 C 0.62001(14) 0.43883(12) 0.31352(6) 0.0112(3) Uani 1 1 d . . . . .
C9 C 0.50171(14) 0.51661(12) 0.29784(7) 0.0118(3) Uani 1 1 d . . . . .
C10 C 0.50832(14) 0.59757(13) 0.24079(7) 0.0136(3) Uani 1 1 d . . . . .
H10 H 0.4293 0.6507 0.2297 0.016 Uiso 1 1 calc R U . . .
C11 C 0.62565(14) 0.60266(13) 0.20035(6) 0.0132(3) Uani 1 1 d . . . . .
H11 H 0.6264 0.6575 0.1614 0.016 Uiso 1 1 calc R U . . .
C12 C 0.87874(14) 0.63030(12) 0.12597(6) 0.0118(3) Uani 1 1 d . . . . .
C13 C 0.88244(14) 0.75874(12) 0.14300(7) 0.0137(3) Uani 1 1 d . . . . .
H13 H 0.8778 0.7846 0.1898 0.016 Uiso 1 1 calc R U . . .
C14 C 0.89305(15) 0.84979(13) 0.09091(7) 0.0158(3) Uani 1 1 d . . . . .
H14 H 0.8942 0.9379 0.1022 0.019 Uiso 1 1 calc R U . . .
C15 C 0.90194(17) 0.81200(14) 0.02262(7) 0.0203(3) Uani 1 1 d . . . . .
H15 H 0.9092 0.8741 -0.0127 0.024 Uiso 1 1 calc R U . . .
C16 C 0.90016(18) 0.68338(15) 0.00617(7) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.9074 0.6574 -0.0405 0.028 Uiso 1 1 calc R U . . .
C17 C 0.88789(17) 0.59219(14) 0.05767(7) 0.0181(3) Uani 1 1 d . . . . .
H17 H 0.8858 0.5041 0.0462 0.022 Uiso 1 1 calc R U . . .
C18 C 0.97218(14) 0.43620(12) 0.17860(6) 0.0108(3) Uani 1 1 d . . . . .
C19 C 1.11440(14) 0.47198(13) 0.18378(7) 0.0137(3) Uani 1 1 d . . . . .
H19 H 1.1389 0.5588 0.1917 0.016 Uiso 1 1 calc R U . . .
C20 C 1.22023(15) 0.38146(13) 0.17750(7) 0.0151(3) Uani 1 1 d . . . . .
H20 H 1.3171 0.4067 0.1794 0.018 Uiso 1 1 calc R U . . .
C21 C 1.18500(15) 0.25348(13) 0.16837(6) 0.0137(3) Uani 1 1 d . . . . .
H21 H 1.2575 0.1914 0.1636 0.016 Uiso 1 1 calc R U . . .
C22 C 1.04323(15) 0.21730(13) 0.16635(6) 0.0135(3) Uani 1 1 d . . . . .
H22 H 1.0191 0.1296 0.1622 0.016 Uiso 1 1 calc R U . . .
C23 C 0.93631(14) 0.30803(12) 0.17036(6) 0.0125(3) Uani 1 1 d . . . . .
H23 H 0.8394 0.2829 0.1675 0.015 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2223(17) . ?
O2 C8 1.3619(15) . ?
O2 C2 1.4308(17) . ?
N1 C6 1.3851(17) . ?
N1 C18 1.4328(17) . ?
N1 C12 1.4409(16) . ?
C1 C9 1.4568(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.522(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.532(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.4094(18) . ?
C6 C7 1.4099(17) . ?
C7 C8 1.3871(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4073(18) . ?
C9 C10 1.3987(18) . ?
C10 C11 1.3747(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.3870(18) . ?
C12 C17 1.3906(18) . ?
C13 C14 1.3967(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3910(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3920(19) . ?
C18 C23 1.3938(18) . ?
C19 C20 1.3843(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3891(19) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C2 119.29(10) . . ?
C6 N1 C18 122.80(11) . . ?
C6 N1 C12 120.72(11) . . ?
C18 N1 C12 115.57(10) . . ?
O1 C1 C9 123.89(13) . . ?
O1 C1 H1 118.1 . . ?
C9 C1 H1 118.1 . . ?
O2 C2 C3 107.08(12) . . ?
O2 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
O2 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C2 113.42(14) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 112.01(15) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C11 120.29(11) . . ?
N1 C6 C7 120.34(12) . . ?
C11 C6 C7 119.35(12) . . ?
C8 C7 C6 119.87(12) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 C7 123.67(12) . . ?
O2 C8 C9 115.33(11) . . ?
C7 C8 C9 121.00(12) . . ?
C10 C9 C8 118.08(12) . . ?
C10 C9 C1 120.50(12) . . ?
C8 C9 C1 121.42(12) . . ?
C11 C10 C9 122.05(12) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C6 119.64(12) . . ?
C10 C11 H11 120.2 . . ?
C6 C11 H11 120.2 . . ?
C13 C12 C17 120.31(12) . . ?
C13 C12 N1 120.99(11) . . ?
C17 C12 N1 118.69(12) . . ?
C12 C13 C14 119.52(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.29(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.80(13) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.24(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.83(13) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C23 119.86(12) . . ?
C19 C18 N1 118.62(12) . . ?
C23 C18 N1 121.44(12) . . ?
C20 C19 C18 120.18(12) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.15(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.52(12) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.65(12) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 119.53(13) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?

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
C8 O2 C2 C3 -172.64(12) . . . . ?
O2 C2 C3 C4 -67.06(18) . . . . ?
C2 C3 C4 C5 174.75(16) . . . . ?
C18 N1 C6 C11 -161.15(12) . . . . ?
C12 N1 C6 C11 7.45(18) . . . . ?
C18 N1 C6 C7 20.61(19) . . . . ?
C12 N1 C6 C7 -170.78(11) . . . . ?
N1 C6 C7 C8 178.87(12) . . . . ?
C11 C6 C7 C8 0.62(19) . . . . ?
C2 O2 C8 C7 5.94(19) . . . . ?
C2 O2 C8 C9 -174.08(12) . . . . ?
C6 C7 C8 O2 178.29(12) . . . . ?
C6 C7 C8 C9 -1.69(19) . . . . ?
O2 C8 C9 C10 -178.64(12) . . . . ?
C7 C8 C9 C10 1.34(19) . . . . ?
O2 C8 C9 C1 0.76(18) . . . . ?
C7 C8 C9 C1 -179.26(13) . . . . ?
O1 C1 C9 C10 0.5(2) . . . . ?
O1 C1 C9 C8 -178.90(13) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C1 C9 C10 C11 -179.32(13) . . . . ?
C9 C10 C11 C6 -1.1(2) . . . . ?
N1 C6 C11 C10 -177.47(12) . . . . ?
C7 C6 C11 C10 0.78(19) . . . . ?
C6 N1 C12 C13 64.29(18) . . . . ?
C18 N1 C12 C13 -126.32(13) . . . . ?
C6 N1 C12 C17 -115.88(15) . . . . ?
C18 N1 C12 C17 53.52(17) . . . . ?
C17 C12 C13 C14 1.1(2) . . . . ?
N1 C12 C13 C14 -179.10(12) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?
N1 C12 C17 C16 179.87(14) . . . . ?
C15 C16 C17 C12 -0.6(2) . . . . ?
C6 N1 C18 C19 -135.04(13) . . . . ?
C12 N1 C18 C19 55.81(16) . . . . ?
C6 N1 C18 C23 48.25(17) . . . . ?
C12 N1 C18 C23 -120.90(13) . . . . ?
C23 C18 C19 C20 3.08(19) . . . . ?
N1 C18 C19 C20 -173.68(11) . . . . ?
C18 C19 C20 C21 -2.26(19) . . . . ?
C19 C20 C21 C22 -0.66(19) . . . . ?
C20 C21 C22 C23 2.78(19) . . . . ?
C21 C22 C23 C18 -1.95(19) . . . . ?
C19 C18 C23 C22 -0.98(18) . . . . ?
N1 C18 C23 C22 175.69(11) . . . . ?

_refine_diff_density_max         1.054
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_SPA106
_database_code_depnum_ccdc_archive 'CCDC 1485288'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
7-(5-(diphenylamino)-2-formylphenoxy)heptanenitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N2 O2'
_chemical_formula_sum            'C25 H24 N2 O2'
_chemical_formula_weight         384.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.609(2)
_cell_length_b                   9.1180(18)
_cell_length_c                   20.524(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.51(3)
_cell_angle_gamma                90
_cell_volume                     2128.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    46457
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.748

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17382
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             4563
_reflns_number_gt                1745
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1263P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.060(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4563
_refine_ls_number_parameters     262
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.2277
_refine_ls_wR_factor_gt          0.1723
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.922
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41070(18) 0.0572(3) 0.62359(10) 0.1246(9) Uani 1 1 d . . . . .
O2 O 0.49500(17) 0.2646(2) 0.47068(9) 0.0953(7) Uani 1 1 d . . . . .
N1 N 0.17340(17) 0.0491(3) 0.31342(10) 0.0846(7) Uani 1 1 d . . . . .
N2 N 1.0497(3) 0.7725(4) 0.5089(2) 0.1661(15) Uani 1 1 d . . . . .
C1 C 0.4390(3) 0.1087(4) 0.57529(14) 0.0984(10) Uani 1 1 d . . . . .
H1 H 0.5097 0.1599 0.5813 0.118 Uiso 1 1 calc R U . . .
C2 C 0.5415(3) 0.3332(4) 0.41913(14) 0.0979(9) Uani 1 1 d . . . . .
H2A H 0.4838 0.3991 0.3938 0.117 Uiso 1 1 calc R U . . .
H2B H 0.5621 0.2599 0.3891 0.117 Uiso 1 1 calc R U . . .
C3 C 0.6487(3) 0.4170(4) 0.45164(17) 0.1158(12) Uani 1 1 d . . . . .
H3A H 0.6266 0.4848 0.4835 0.139 Uiso 1 1 calc R U . A 1
H3B H 0.7050 0.3485 0.4763 0.139 Uiso 1 1 calc R U . A 1
C4A C 0.7071(4) 0.5006(5) 0.4058(2) 0.1592(19) Uani 0.533(8) 1 d D . P B 1
H4A1 H 0.6539 0.5681 0.3783 0.191 Uiso 0.533(8) 1 calc R U P B 1
H4A2 H 0.7440 0.4371 0.3780 0.191 Uiso 0.533(8) 1 calc R U P B 1
C5A C 0.8023(5) 0.5843(7) 0.4619(3) 0.094(2) Uiso 0.533(8) 1 d D . P B 1
H5A1 H 0.7635 0.6358 0.4929 0.113 Uiso 0.533(8) 1 calc R U P B 1
H5A2 H 0.8580 0.5150 0.4866 0.113 Uiso 0.533(8) 1 calc R U P B 1
C6A C 0.8633(6) 0.6900(8) 0.4245(4) 0.109(2) Uiso 0.533(8) 1 d D . P B 1
H6A1 H 0.8130 0.7721 0.4076 0.131 Uiso 0.533(8) 1 calc R U P B 1
H6A2 H 0.8904 0.6426 0.3880 0.131 Uiso 0.533(8) 1 calc R U P B 1
C4B C 0.7071(4) 0.5006(5) 0.4058(2) 0.1592(19) Uani 0.467(8) 1 d D . P B 2
H4B1 H 0.6622 0.5906 0.3967 0.191 Uiso 0.467(8) 1 calc R U P B 2
H4B2 H 0.6923 0.4453 0.3646 0.191 Uiso 0.467(8) 1 calc R U P B 2
C5B C 0.8401(6) 0.5488(8) 0.4165(4) 0.108(3) Uiso 0.467(8) 1 d D . P B 2
H5B1 H 0.8922 0.4717 0.4375 0.130 Uiso 0.467(8) 1 calc R U P B 2
H5B2 H 0.8616 0.5763 0.3749 0.130 Uiso 0.467(8) 1 calc R U P B 2
C6B C 0.8419(7) 0.6788(10) 0.4618(5) 0.119(3) Uiso 0.467(8) 1 d D . P B 2
H6B1 H 0.7889 0.7540 0.4399 0.143 Uiso 0.467(8) 1 calc R U P B 2
H6B2 H 0.8163 0.6497 0.5021 0.143 Uiso 0.467(8) 1 calc R U P B 2
C7 C 0.9645(4) 0.7370(5) 0.4785(3) 0.1555(18) Uani 1 1 d D . . . .
C8 C 0.2398(2) 0.0663(3) 0.37833(12) 0.0775(7) Uani 1 1 d . . . . .
C9 C 0.3355(2) 0.1607(3) 0.39082(12) 0.0803(8) Uani 1 1 d . . . . .
H9 H 0.3557 0.2143 0.3562 0.096 Uiso 1 1 calc R U . . .
C10 C 0.4006(2) 0.1751(3) 0.45455(12) 0.0795(8) Uani 1 1 d . . . . .
C11 C 0.3700(2) 0.0965(3) 0.50752(12) 0.0802(8) Uani 1 1 d . . . . .
C12 C 0.2728(2) 0.0075(3) 0.49406(13) 0.0860(8) Uani 1 1 d . . . . .
H12 H 0.2500 -0.0428 0.5288 0.103 Uiso 1 1 calc R U . . .
C13 C 0.2081(2) -0.0096(3) 0.43068(13) 0.0864(8) Uani 1 1 d . . . . .
H13 H 0.1433 -0.0718 0.4229 0.104 Uiso 1 1 calc R U . . .
C14 C 0.0547(2) 0.0013(4) 0.30428(13) 0.0859(8) Uani 1 1 d . . . . .
C15 C -0.0257(3) 0.0827(4) 0.32981(15) 0.1102(11) Uani 1 1 d . . . . .
H15 H -0.0027 0.1694 0.3526 0.132 Uiso 1 1 calc R U . . .
C16 C -0.1407(3) 0.0353(6) 0.3215(2) 0.1380(15) Uani 1 1 d . . . . .
H16 H -0.1949 0.0890 0.3394 0.166 Uiso 1 1 calc R U . . .
C17 C -0.1752(4) -0.0917(7) 0.2865(2) 0.1508(19) Uani 1 1 d . . . . .
H17 H -0.2532 -0.1217 0.2795 0.181 Uiso 1 1 calc R U . . .
C18 C -0.0941(4) -0.1737(6) 0.26197(18) 0.1344(14) Uani 1 1 d . . . . .
H18 H -0.1169 -0.2610 0.2397 0.161 Uiso 1 1 calc R U . . .
C19 C 0.0206(3) -0.1272(4) 0.27029(14) 0.1039(10) Uani 1 1 d . . . . .
H19 H 0.0751 -0.1821 0.2531 0.125 Uiso 1 1 calc R U . . .
C20 C 0.2266(2) 0.0528(3) 0.25712(12) 0.0753(7) Uani 1 1 d . . . . .
C21 C 0.1673(3) 0.1151(3) 0.19842(13) 0.0871(8) Uani 1 1 d . . . . .
H21 H 0.0935 0.1565 0.1964 0.105 Uiso 1 1 calc R U . . .
C22 C 0.2170(3) 0.1160(4) 0.14338(15) 0.1060(10) Uani 1 1 d . . . . .
H22 H 0.1763 0.1578 0.1041 0.127 Uiso 1 1 calc R U . . .
C23 C 0.3248(4) 0.0567(4) 0.14526(16) 0.1121(11) Uani 1 1 d . . . . .
H23 H 0.3575 0.0577 0.1074 0.135 Uiso 1 1 calc R U . . .
C24 C 0.3855(3) -0.0048(4) 0.20320(16) 0.1032(10) Uani 1 1 d . . . . .
H24 H 0.4595 -0.0454 0.2046 0.124 Uiso 1 1 calc R U . . .
C25 C 0.3372(3) -0.0064(3) 0.25882(14) 0.0879(8) Uani 1 1 d . . . . .
H25 H 0.3788 -0.0475 0.2980 0.106 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.201(3) . ?
O2 C10 1.353(3) . ?
O2 C2 1.425(4) . ?
N1 C8 1.409(3) . ?
N1 C20 1.415(3) . ?
N1 C14 1.422(3) . ?
N2 C7 1.108(5) . ?
C1 C11 1.464(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.499(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4B 1.475(5) . ?
C3 C4A 1.475(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4A C5A 1.620(6) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.496(10) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7 1.507(7) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C4B C5B 1.579(8) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C6B 1.504(11) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B C7 1.494(9) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C8 C13 1.388(4) . ?
C8 C9 1.388(4) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.406(4) . ?
C11 C12 1.373(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 C19 1.380(4) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 C25 1.388(4) . ?
C21 C22 1.367(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C2 119.4(2) . . ?
C8 N1 C20 121.6(2) . . ?
C8 N1 C14 119.5(2) . . ?
C20 N1 C14 118.0(2) . . ?
O1 C1 C11 124.5(3) . . ?
O1 C1 H1 117.8 . . ?
C11 C1 H1 117.8 . . ?
O2 C2 C3 107.3(2) . . ?
O2 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
O2 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
C4B C3 C2 115.2(3) . . ?
C4A C3 C2 115.2(3) . . ?
C4A C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4A C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4A C5A 97.2(4) . . ?
C3 C4A H4A1 112.3 . . ?
C5A C4A H4A1 112.3 . . ?
C3 C4A H4A2 112.3 . . ?
C5A C4A H4A2 112.3 . . ?
H4A1 C4A H4A2 109.9 . . ?
C6A C5A C4A 105.3(5) . . ?
C6A C5A H5A1 110.7 . . ?
C4A C5A H5A1 110.7 . . ?
C6A C5A H5A2 110.7 . . ?
C4A C5A H5A2 110.7 . . ?
H5A1 C5A H5A2 108.8 . . ?
C5A C6A C7 100.7(5) . . ?
C5A C6A H6A1 111.6 . . ?
C7 C6A H6A1 111.6 . . ?
C5A C6A H6A2 111.6 . . ?
C7 C6A H6A2 111.6 . . ?
H6A1 C6A H6A2 109.4 . . ?
C3 C4B C5B 128.0(4) . . ?
C3 C4B H4B1 105.3 . . ?
C5B C4B H4B1 105.3 . . ?
C3 C4B H4B2 105.3 . . ?
C5B C4B H4B2 105.3 . . ?
H4B1 C4B H4B2 106.0 . . ?
C6B C5B C4B 101.4(6) . . ?
C6B C5B H5B1 111.5 . . ?
C4B C5B H5B1 111.5 . . ?
C6B C5B H5B2 111.5 . . ?
C4B C5B H5B2 111.5 . . ?
H5B1 C5B H5B2 109.3 . . ?
C7 C6B C5B 108.4(6) . . ?
C7 C6B H6B1 110.0 . . ?
C5B C6B H6B1 110.0 . . ?
C7 C6B H6B2 110.0 . . ?
C5B C6B H6B2 110.0 . . ?
H6B1 C6B H6B2 108.4 . . ?
N2 C7 C6B 159.4(7) . . ?
N2 C7 C6A 167.3(6) . . ?
C13 C8 C9 119.5(2) . . ?
C13 C8 N1 119.8(2) . . ?
C9 C8 N1 120.7(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O2 C10 C9 123.6(3) . . ?
O2 C10 C11 115.8(2) . . ?
C9 C10 C11 120.6(3) . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 C1 120.6(3) . . ?
C10 C11 C1 121.4(3) . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C8 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C15 C14 C19 120.2(3) . . ?
C15 C14 N1 119.9(3) . . ?
C19 C14 N1 119.9(3) . . ?
C14 C15 C16 119.7(4) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C21 C20 C25 118.6(3) . . ?
C21 C20 N1 119.9(2) . . ?
C25 C20 N1 121.5(2) . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?

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
C10 O2 C2 C3 -176.6(3) . . . . ?
O2 C2 C3 C4B -177.9(3) . . . . ?
O2 C2 C3 C4A -177.9(3) . . . . ?
C2 C3 C4A C5A 173.4(4) . . . . ?
C3 C4A C5A C6A -173.8(5) . . . . ?
C4A C5A C6A C7 -168.6(4) . . . . ?
C2 C3 C4B C5B -154.6(5) . . . . ?
C3 C4B C5B C6B -78.3(8) . . . . ?
C4B C5B C6B C7 178.7(6) . . . . ?
C5B C6B C7 N2 -123.3(15) . . . . ?
C5A C6A C7 N2 145(2) . . . . ?
C20 N1 C8 C13 -145.6(3) . . . . ?
C14 N1 C8 C13 23.1(4) . . . . ?
C20 N1 C8 C9 35.6(4) . . . . ?
C14 N1 C8 C9 -155.7(3) . . . . ?
C13 C8 C9 C10 2.0(4) . . . . ?
N1 C8 C9 C10 -179.2(2) . . . . ?
C2 O2 C10 C9 -9.1(4) . . . . ?
C2 O2 C10 C11 171.7(2) . . . . ?
C8 C9 C10 O2 179.9(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
O2 C10 C11 C12 178.1(2) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
O2 C10 C11 C1 -1.7(4) . . . . ?
C9 C10 C11 C1 179.1(3) . . . . ?
O1 C1 C11 C12 -8.1(5) . . . . ?
O1 C1 C11 C10 171.7(3) . . . . ?
C10 C11 C12 C13 2.1(4) . . . . ?
C1 C11 C12 C13 -178.1(3) . . . . ?
C11 C12 C13 C8 -1.0(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
N1 C8 C13 C12 -179.9(2) . . . . ?
C8 N1 C14 C15 59.7(4) . . . . ?
C20 N1 C14 C15 -131.2(3) . . . . ?
C8 N1 C14 C19 -119.8(3) . . . . ?
C20 N1 C14 C19 49.4(4) . . . . ?
C19 C14 C15 C16 0.2(5) . . . . ?
N1 C14 C15 C16 -179.3(3) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C18 2.3(7) . . . . ?
C16 C17 C18 C19 -2.1(6) . . . . ?
C17 C18 C19 C14 1.0(5) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
N1 C14 C19 C18 179.5(3) . . . . ?
C8 N1 C20 C21 -144.2(3) . . . . ?
C14 N1 C20 C21 46.9(4) . . . . ?
C8 N1 C20 C25 36.5(4) . . . . ?
C14 N1 C20 C25 -132.4(3) . . . . ?
C25 C20 C21 C22 0.8(4) . . . . ?
N1 C20 C21 C22 -178.5(3) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C21 C20 C25 C24 -0.9(4) . . . . ?
N1 C20 C25 C24 178.3(3) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_SPA105
_database_code_depnum_ccdc_archive 'CCDC 1485287'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-(diphenylamino)-2-hexyloxybenzaldehyde
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N O2'
_chemical_formula_sum            'C25 H25 N O2'
_chemical_formula_weight         371.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.565(2)
_cell_length_b                   9.822(2)
_cell_length_c                   20.676(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.89(3)
_cell_angle_gamma                90
_cell_volume                     2142.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    37609
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17003
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4711
_reflns_number_gt                1741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL ADSC Quantum-210 ADX Program(Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5(Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND(Putz, Brandenburg, 2007)'
_computing_publication_material  'enCIFer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1284P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.091(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4711
_refine_ls_number_parameters     297
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1774
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.829
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68394(18) 0.5602(2) 0.19717(10) 0.1130(7) Uani 1 1 d . . . . .
O2 O 0.35971(15) 0.36834(18) 0.14977(9) 0.0918(6) Uani 1 1 d . . . . .
N1 N 0.16197(19) 0.52385(19) 0.34117(10) 0.0830(6) Uani 1 1 d . . . . .
C1 C 0.5854(3) 0.5006(3) 0.18459(13) 0.0920(8) Uani 1 1 d . . . . .
H1 H 0.5798 0.4475 0.1473 0.110 Uiso 1 1 calc R U . . .
C2 C 0.2443(3) 0.3030(4) 0.12762(16) 0.1378(14) Uani 1 1 d D . . . .
C3A C 0.2825(8) 0.2020(6) 0.0737(3) 0.102(2) Uani 0.544(8) 1 d D . P A 1
H3A1 H 0.3621 0.1570 0.0853 0.122 Uiso 0.544(8) 1 calc R U P A 1
H3A2 H 0.2174 0.1340 0.0649 0.122 Uiso 0.544(8) 1 calc R U P A 1
C4A C 0.2950(10) 0.2970(10) 0.0163(3) 0.147(4) Uani 0.544(8) 1 d D . P A 1
H4A1 H 0.3386 0.3779 0.0325 0.177 Uiso 0.544(8) 1 calc R U P A 1
H4A2 H 0.2099 0.3251 0.0024 0.177 Uiso 0.544(8) 1 calc R U P A 1
C5A C 0.3612(10) 0.2523(14) -0.0449(6) 0.39(2) Uani 0.544(8) 1 d D . P A 1
H5A1 H 0.3305 0.1630 -0.0581 0.466 Uiso 0.544(8) 1 calc R U P A 1
H5A2 H 0.3398 0.3156 -0.0798 0.466 Uiso 0.544(8) 1 calc R U P A 1
C6A C 0.5035(9) 0.2472(14) -0.0336(6) 0.184(5) Uani 0.544(8) 1 d D . P A 1
H6A1 H 0.5346 0.3361 -0.0201 0.221 Uiso 0.544(8) 1 calc R U P A 1
H6A2 H 0.5255 0.1828 0.0007 0.221 Uiso 0.544(8) 1 calc R U P A 1
C7A C 0.5655(15) 0.2050(14) -0.0944(6) 0.195(5) Uani 0.544(8) 1 d D . P A 1
H7A1 H 0.5970 0.1136 -0.0895 0.292 Uiso 0.544(8) 1 calc R U P A 1
H7A2 H 0.6346 0.2654 -0.1020 0.292 Uiso 0.544(8) 1 calc R U P A 1
H7A3 H 0.5046 0.2089 -0.1304 0.292 Uiso 0.544(8) 1 calc R U P A 1
C3B C 0.2612(8) 0.2975(13) 0.0518(4) 0.134(5) Uani 0.456(8) 1 d D . P A 2
H3B1 H 0.1801 0.2837 0.0287 0.160 Uiso 0.456(8) 1 calc R U P A 2
H3B2 H 0.2979 0.3817 0.0369 0.160 Uiso 0.456(8) 1 calc R U P A 2
C4B C 0.3483(10) 0.1798(10) 0.0408(4) 0.146(4) Uani 0.456(8) 1 d D . P A 2
H4B1 H 0.3080 0.0967 0.0547 0.175 Uiso 0.456(8) 1 calc R U P A 2
H4B2 H 0.4254 0.1920 0.0676 0.175 Uiso 0.456(8) 1 calc R U P A 2
C5B C 0.3833(9) 0.1629(12) -0.0297(4) 0.133(4) Uani 0.456(8) 1 d D . P A 2
H5B1 H 0.3121 0.1668 -0.0611 0.159 Uiso 0.456(8) 1 calc R U P A 2
H5B2 H 0.4385 0.0864 -0.0375 0.159 Uiso 0.456(8) 1 calc R U P A 2
C6B C 0.452(2) 0.299(2) -0.0177(17) 0.41(2) Uiso 0.456(8) 1 d D . P A 2
H6B1 H 0.4796 0.3159 0.0270 0.497 Uiso 0.456(8) 1 calc R U P A 2
H6B2 H 0.4092 0.3775 -0.0372 0.497 Uiso 0.456(8) 1 calc R U P A 2
C7B C 0.553(2) 0.233(3) -0.0595(10) 0.301(14) Uani 0.456(8) 1 d D . P A 2
H7B1 H 0.6142 0.1856 -0.0320 0.451 Uiso 0.456(8) 1 calc R U P A 2
H7B2 H 0.5955 0.3033 -0.0828 0.451 Uiso 0.456(8) 1 calc R U P A 2
H7B3 H 0.5132 0.1708 -0.0897 0.451 Uiso 0.456(8) 1 calc R U P A 2
C8 C 0.2661(2) 0.5178(2) 0.30228(12) 0.0758(7) Uani 1 1 d . . . . .
C9 C 0.2599(2) 0.4430(2) 0.24564(11) 0.0748(7) Uani 1 1 d . . . . .
H9 H 0.1861 0.3958 0.2336 0.090 Uiso 1 1 calc R U . . .
C10 C 0.3629(2) 0.4375(2) 0.20641(11) 0.0741(6) Uani 1 1 d . . . . .
C11 C 0.4753(2) 0.5064(2) 0.22390(12) 0.0781(7) Uani 1 1 d . . . . .
C12 C 0.4791(2) 0.5808(3) 0.28062(14) 0.0889(8) Uani 1 1 d . . . . .
H12 H 0.5529 0.6281 0.2927 0.107 Uiso 1 1 calc R U . . .
C13 C 0.3781(2) 0.5878(3) 0.32010(13) 0.0885(8) Uani 1 1 d . . . . .
H13 H 0.3842 0.6383 0.3582 0.106 Uiso 1 1 calc R U . . .
C14 C 0.1471(2) 0.6307(2) 0.38746(12) 0.0781(7) Uani 1 1 d . . . . .
C15 C 0.1584(2) 0.7667(3) 0.36998(14) 0.0908(8) Uani 1 1 d . . . . .
H15 H 0.1760 0.7896 0.3277 0.109 Uiso 1 1 calc R U . . .
C16 C 0.1436(3) 0.8665(3) 0.41483(17) 0.1020(9) Uani 1 1 d . . . . .
H16 H 0.1535 0.9573 0.4033 0.122 Uiso 1 1 calc R U . . .
C17 C 0.1143(3) 0.8342(3) 0.47670(18) 0.1094(10) Uani 1 1 d . . . . .
H17 H 0.1039 0.9028 0.5070 0.131 Uiso 1 1 calc R U . . .
C18 C 0.1003(3) 0.7013(3) 0.49381(14) 0.1039(9) Uani 1 1 d . . . . .
H18 H 0.0786 0.6792 0.5356 0.125 Uiso 1 1 calc R U . . .
C19 C 0.1181(2) 0.6001(3) 0.44953(13) 0.0892(8) Uani 1 1 d . . . . .
H19 H 0.1104 0.5095 0.4618 0.107 Uiso 1 1 calc R U . . .
C20 C 0.0594(2) 0.4295(2) 0.33292(11) 0.0746(6) Uani 1 1 d . . . . .
C21 C -0.0630(3) 0.4780(3) 0.32375(12) 0.0900(8) Uani 1 1 d . . . . .
H21 H -0.0774 0.5713 0.3212 0.108 Uiso 1 1 calc R U . . .
C22 C -0.1639(3) 0.3891(4) 0.31833(13) 0.1007(9) Uani 1 1 d . . . . .
H22 H -0.2460 0.4228 0.3131 0.121 Uiso 1 1 calc R U . . .
C23 C -0.1441(3) 0.2533(4) 0.32059(13) 0.1016(9) Uani 1 1 d . . . . .
H23 H -0.2126 0.1939 0.3170 0.122 Uiso 1 1 calc R U . . .
C24 C -0.0240(3) 0.2029(3) 0.32811(14) 0.0966(9) Uani 1 1 d . . . . .
H24 H -0.0108 0.1093 0.3286 0.116 Uiso 1 1 calc R U . . .
C25 C 0.0790(3) 0.2914(3) 0.33502(12) 0.0850(7) Uani 1 1 d . . . . .
H25 H 0.1608 0.2570 0.3410 0.102 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.212(3) . ?
O2 C10 1.353(3) . ?
O2 C2 1.432(3) . ?
N1 C8 1.397(3) . ?
N1 C20 1.430(3) . ?
N1 C14 1.434(3) . ?
C1 C11 1.454(4) . ?
C1 H1 0.9300 . ?
C2 C3A 1.561(6) . ?
C2 C3B 1.588(8) . ?
C3A C4A 1.521(8) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.539(9) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.511(9) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7A 1.503(9) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C3B C4B 1.502(9) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4B C5B 1.530(8) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C5B C6B 1.535(10) . ?
C5B H5B1 0.9700 . ?
C5B H5B2 0.9700 . ?
C6B C7B 1.551(10) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
C8 C9 1.381(3) . ?
C8 C13 1.402(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.368(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.364(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.372(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.350(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.363(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.395(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C2 119.02(18) . . ?
C8 N1 C20 121.22(19) . . ?
C8 N1 C14 122.1(2) . . ?
C20 N1 C14 116.48(18) . . ?
O1 C1 C11 124.4(3) . . ?
O1 C1 H1 117.8 . . ?
C11 C1 H1 117.8 . . ?
O2 C2 C3A 105.5(3) . . ?
O2 C2 C3B 101.2(4) . . ?
C4A C3A C2 101.7(5) . . ?
C4A C3A H3A1 111.4 . . ?
C2 C3A H3A1 111.4 . . ?
C4A C3A H3A2 111.4 . . ?
C2 C3A H3A2 111.4 . . ?
H3A1 C3A H3A2 109.3 . . ?
C3A C4A C5A 121.8(10) . . ?
C3A C4A H4A1 106.9 . . ?
C5A C4A H4A1 106.9 . . ?
C3A C4A H4A2 106.9 . . ?
C5A C4A H4A2 106.9 . . ?
H4A1 C4A H4A2 106.7 . . ?
C6A C5A C4A 111.9(9) . . ?
C6A C5A H5A1 109.2 . . ?
C4A C5A H5A1 109.2 . . ?
C6A C5A H5A2 109.2 . . ?
C4A C5A H5A2 109.2 . . ?
H5A1 C5A H5A2 107.9 . . ?
C7A C6A C5A 110.7(12) . . ?
C7A C6A H6A1 109.5 . . ?
C5A C6A H6A1 109.5 . . ?
C7A C6A H6A2 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 108.1 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C4B C3B C2 106.0(8) . . ?
C4B C3B H3B1 110.5 . . ?
C2 C3B H3B1 110.5 . . ?
C4B C3B H3B2 110.5 . . ?
C2 C3B H3B2 110.5 . . ?
H3B1 C3B H3B2 108.7 . . ?
C3B C4B C5B 114.0(9) . . ?
C3B C4B H4B1 108.8 . . ?
C5B C4B H4B1 108.8 . . ?
C3B C4B H4B2 108.8 . . ?
C5B C4B H4B2 108.8 . . ?
H4B1 C4B H4B2 107.7 . . ?
C4B C5B C6B 83.5(12) . . ?
C4B C5B H5B1 114.7 . . ?
C6B C5B H5B1 114.7 . . ?
C4B C5B H5B2 114.7 . . ?
C6B C5B H5B2 114.7 . . ?
H5B1 C5B H5B2 111.8 . . ?
C5B C6B C7B 83.2(13) . . ?
C5B C6B H6B1 114.8 . . ?
C7B C6B H6B1 114.8 . . ?
C5B C6B H6B2 114.8 . . ?
C7B C6B H6B2 114.8 . . ?
H6B1 C6B H6B2 111.8 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9 C8 N1 120.4(2) . . ?
C9 C8 C13 119.2(2) . . ?
N1 C8 C13 120.5(2) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O2 C10 C9 122.6(2) . . ?
O2 C10 C11 116.8(2) . . ?
C9 C10 C11 120.6(2) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C1 120.4(2) . . ?
C10 C11 C1 122.0(2) . . ?
C13 C12 C11 122.6(2) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C8 119.3(2) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C19 C14 C15 118.8(2) . . ?
C19 C14 N1 120.2(2) . . ?
C15 C14 N1 121.1(2) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.8(3) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C25 C20 C21 119.0(2) . . ?
C25 C20 N1 121.6(2) . . ?
C21 C20 N1 119.4(2) . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 119.8(3) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O2 C2 C3A -164.6(3) . . . . ?
C10 O2 C2 C3B 155.2(4) . . . . ?
O2 C2 C3A C4A -78.7(6) . . . . ?
C2 C3A C4A C5A 165.5(9) . . . . ?
C3A C4A C5A C6A -74.4(13) . . . . ?
C4A C5A C6A C7A -179.3(11) . . . . ?
O2 C2 C3B C4B 79.1(8) . . . . ?
C2 C3B C4B C5B -176.3(7) . . . . ?
C3B C4B C5B C6B 66.6(15) . . . . ?
C4B C5B C6B C7B 141(2) . . . . ?
C20 N1 C8 C9 15.4(3) . . . . ?
C14 N1 C8 C9 -159.4(2) . . . . ?
C20 N1 C8 C13 -164.8(2) . . . . ?
C14 N1 C8 C13 20.4(3) . . . . ?
N1 C8 C9 C10 179.4(2) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C2 O2 C10 C9 2.9(4) . . . . ?
C2 O2 C10 C11 -176.2(3) . . . . ?
C8 C9 C10 O2 -178.3(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
O2 C10 C11 C12 178.2(2) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
O2 C10 C11 C1 -2.2(3) . . . . ?
C9 C10 C11 C1 178.8(2) . . . . ?
O1 C1 C11 C12 -1.6(4) . . . . ?
O1 C1 C11 C10 178.7(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C1 C11 C12 C13 -178.9(2) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 C12 0.3(4) . . . . ?
N1 C8 C13 C12 -179.5(2) . . . . ?
C8 N1 C14 C19 -131.4(3) . . . . ?
C20 N1 C14 C19 53.6(3) . . . . ?
C8 N1 C14 C15 50.4(3) . . . . ?
C20 N1 C14 C15 -124.7(3) . . . . ?
C19 C14 C15 C16 1.6(4) . . . . ?
N1 C14 C15 C16 179.9(2) . . . . ?
C14 C15 C16 C17 -1.8(4) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
N1 C14 C19 C18 -178.3(2) . . . . ?
C17 C18 C19 C14 -1.5(4) . . . . ?
C8 N1 C20 C25 55.0(3) . . . . ?
C14 N1 C20 C25 -130.0(2) . . . . ?
C8 N1 C20 C21 -126.2(2) . . . . ?
C14 N1 C20 C21 48.9(3) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
N1 C20 C21 C22 -177.4(2) . . . . ?
C20 C21 C22 C23 -1.4(4) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 1.5(4) . . . . ?
C21 C20 C25 C24 -0.2(3) . . . . ?
N1 C20 C25 C24 178.6(2) . . . . ?
C23 C24 C25 C20 -1.3(4) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_spa4
_database_code_depnum_ccdc_archive 'CCDC 1571829'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-(diphenylamino)-2-methoxybenzaldehyde '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O2'
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2540(19)
_cell_length_b                   10.441(2)
_cell_length_c                   16.144(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.15(3)
_cell_angle_gamma                90
_cell_volume                     1547.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    54826
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.60999
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15214
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4128
_reflns_number_gt                3690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
'PAL ADSC Quantum-210 ADX Program (Arvai & Nielsen, 1983)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, L. J. 2012)'
_computing_publication_material  'EnCifer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.4763P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4128
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47373(8) 0.08022(7) 0.39701(4) 0.01473(15) Uani 1 1 d . . . . .
O2 O 0.05970(9) -0.03484(8) 0.37187(5) 0.02191(18) Uani 1 1 d . . . . .
N1 N 0.39768(8) 0.37662(7) 0.62035(5) 0.01020(16) Uani 1 1 d . . . . .
C15 C 0.29997(9) 0.47947(8) 0.63216(5) 0.00919(17) Uani 1 1 d . . . . .
C4 C 0.44333(9) 0.22748(8) 0.50967(5) 0.00921(17) Uani 1 1 d . . . . .
H4 H 0.5418 0.2549 0.5134 0.011 Uiso 1 1 calc R U . . .
C5 C 0.39068(10) 0.13513(8) 0.45103(5) 0.00935(17) Uani 1 1 d . . . . .
C16 C 0.29850(10) 0.53232(9) 0.71143(6) 0.01262(18) Uani 1 1 d . . . . .
H16 H 0.3611 0.4995 0.7577 0.015 Uiso 1 1 calc R U . . .
C6 C 0.24486(10) 0.09424(8) 0.44444(5) 0.01012(17) Uani 1 1 d . . . . .
C7 C 0.15559(10) 0.14418(8) 0.50052(5) 0.01073(17) Uani 1 1 d . . . . .
H7 H 0.0579 0.1151 0.4980 0.013 Uiso 1 1 calc R U . . .
C8 C 0.20603(9) 0.23457(8) 0.55934(5) 0.01084(17) Uani 1 1 d . . . . .
H8 H 0.1439 0.2664 0.5972 0.013 Uiso 1 1 calc R U . . .
C3 C 0.34997(9) 0.27945(8) 0.56297(5) 0.00889(17) Uani 1 1 d . . . . .
C14 C 0.63667(10) 0.29448(9) 0.67773(6) 0.01330(18) Uani 1 1 d . . . . .
H14 H 0.5942 0.2132 0.6857 0.016 Uiso 1 1 calc R U . . .
C9 C 0.54930(9) 0.39631(8) 0.64512(5) 0.00898(17) Uani 1 1 d . . . . .
C18 C 0.11203(10) 0.68220(9) 0.65530(7) 0.0165(2) Uani 1 1 d . . . . .
H18 H 0.0478 0.7508 0.6633 0.020 Uiso 1 1 calc R U . . .
C20 C 0.20844(10) 0.52915(9) 0.56458(6) 0.01244(18) Uani 1 1 d . . . . .
H20 H 0.2105 0.4944 0.5103 0.015 Uiso 1 1 calc R U . . .
C17 C 0.20462(11) 0.63358(9) 0.72226(6) 0.01573(19) Uani 1 1 d . . . . .
H17 H 0.2039 0.6699 0.7762 0.019 Uiso 1 1 calc R U . . .
C19 C 0.11433(11) 0.62936(9) 0.57643(6) 0.01613(19) Uani 1 1 d . . . . .
H19 H 0.0512 0.6620 0.5303 0.019 Uiso 1 1 calc R U . . .
C2 C 0.18568(11) 0.00234(9) 0.38048(6) 0.01424(18) Uani 1 1 d . . . . .
H2 H 0.2491 -0.0302 0.3436 0.017 Uiso 1 1 calc R U . . .
C1 C 0.61648(11) 0.12986(9) 0.39364(6) 0.01608(19) Uani 1 1 d . . . . .
H1A H 0.6100 0.2209 0.3788 0.024 Uiso 1 1 calc R U . . .
H1B H 0.6629 0.0830 0.3515 0.024 Uiso 1 1 calc R U . . .
H1C H 0.6745 0.1199 0.4483 0.024 Uiso 1 1 calc R U . . .
C10 C 0.61204(10) 0.51601(8) 0.63660(6) 0.01130(17) Uani 1 1 d . . . . .
H10 H 0.5529 0.5861 0.6157 0.014 Uiso 1 1 calc R U . . .
C12 C 0.84879(10) 0.43141(9) 0.68864(6) 0.01443(19) Uani 1 1 d . . . . .
H12 H 0.9508 0.4429 0.7023 0.017 Uiso 1 1 calc R U . . .
C11 C 0.76091(10) 0.53336(9) 0.65850(6) 0.01347(18) Uani 1 1 d . . . . .
H11 H 0.8028 0.6155 0.6528 0.016 Uiso 1 1 calc R U . . .
C13 C 0.78556(10) 0.31213(9) 0.69854(6) 0.01564(19) Uani 1 1 d . . . . .
H13 H 0.8448 0.2423 0.7197 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3589(11) . ?
O1 C1 1.4264(12) . ?
O2 C2 1.2201(12) . ?
N1 C3 1.4073(11) . ?
N1 C9 1.4252(12) . ?
N1 C15 1.4318(11) . ?
C15 C16 1.3952(12) . ?
C15 C20 1.3953(13) . ?
C4 C5 1.3958(12) . ?
C4 C3 1.4023(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.4067(12) . ?
C16 C17 1.3932(13) . ?
C16 H16 0.9500 . ?
C6 C7 1.4001(12) . ?
C6 C2 1.4650(12) . ?
C7 C8 1.3783(12) . ?
C7 H7 0.9500 . ?
C8 C3 1.4063(12) . ?
C8 H8 0.9500 . ?
C14 C13 1.3893(13) . ?
C14 C9 1.3983(12) . ?
C14 H14 0.9500 . ?
C9 C10 1.3920(12) . ?
C18 C17 1.3893(15) . ?
C18 C19 1.3903(14) . ?
C18 H18 0.9500 . ?
C20 C19 1.3897(13) . ?
C20 H20 0.9500 . ?
C17 H17 0.9500 . ?
C19 H19 0.9500 . ?
C2 H2 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 C11 1.3909(13) . ?
C10 H10 0.9500 . ?
C12 C11 1.3901(13) . ?
C12 C13 1.3936(14) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13 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
C5 O1 C1 118.14(7) . . ?
C3 N1 C9 120.40(7) . . ?
C3 N1 C15 118.47(7) . . ?
C9 N1 C15 118.07(7) . . ?
C16 C15 C20 119.73(8) . . ?
C16 C15 N1 119.81(8) . . ?
C20 C15 N1 120.44(8) . . ?
C5 C4 C3 119.59(8) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
O1 C5 C4 123.31(8) . . ?
O1 C5 C6 115.92(8) . . ?
C4 C5 C6 120.76(8) . . ?
C17 C16 C15 119.52(9) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C7 C6 C5 118.41(8) . . ?
C7 C6 C2 120.05(8) . . ?
C5 C6 C2 121.54(8) . . ?
C8 C7 C6 121.60(8) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C3 119.65(8) . . ?
C7 C8 H8 120.2 . . ?
C3 C8 H8 120.2 . . ?
C4 C3 C8 119.88(8) . . ?
C4 C3 N1 121.07(8) . . ?
C8 C3 N1 119.05(8) . . ?
C13 C14 C9 119.98(8) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C10 C9 C14 119.42(8) . . ?
C10 C9 N1 120.65(8) . . ?
C14 C9 N1 119.93(8) . . ?
C17 C18 C19 119.31(9) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C19 C20 C15 120.14(8) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C18 C17 C16 120.89(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C20 C19 C18 120.40(9) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
O2 C2 C6 123.84(9) . . ?
O2 C2 H2 118.1 . . ?
C6 C2 H2 118.1 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C10 C9 120.26(8) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C11 C12 C13 119.26(9) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C11 C10 120.47(8) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C14 C13 C12 120.58(9) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?

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
C3 N1 C15 C16 143.58(9) . . . . ?
C9 N1 C15 C16 -56.12(11) . . . . ?
C3 N1 C15 C20 -37.87(12) . . . . ?
C9 N1 C15 C20 122.43(9) . . . . ?
C1 O1 C5 C4 -7.41(13) . . . . ?
C1 O1 C5 C6 172.06(8) . . . . ?
C3 C4 C5 O1 179.86(8) . . . . ?
C3 C4 C5 C6 0.42(12) . . . . ?
C20 C15 C16 C17 0.52(13) . . . . ?
N1 C15 C16 C17 179.09(8) . . . . ?
O1 C5 C6 C7 177.73(8) . . . . ?
C4 C5 C6 C7 -2.78(13) . . . . ?
O1 C5 C6 C2 -2.66(12) . . . . ?
C4 C5 C6 C2 176.82(8) . . . . ?
C5 C6 C7 C8 2.20(13) . . . . ?
C2 C6 C7 C8 -177.41(8) . . . . ?
C6 C7 C8 C3 0.76(13) . . . . ?
C5 C4 C3 C8 2.58(12) . . . . ?
C5 C4 C3 N1 -177.25(8) . . . . ?
C7 C8 C3 C4 -3.17(13) . . . . ?
C7 C8 C3 N1 176.66(8) . . . . ?
C9 N1 C3 C4 -20.22(12) . . . . ?
C15 N1 C3 C4 139.61(8) . . . . ?
C9 N1 C3 C8 159.95(8) . . . . ?
C15 N1 C3 C8 -40.22(11) . . . . ?
C13 C14 C9 C10 -2.26(13) . . . . ?
C13 C14 C9 N1 177.22(8) . . . . ?
C3 N1 C9 C10 124.92(9) . . . . ?
C15 N1 C9 C10 -34.98(11) . . . . ?
C3 N1 C9 C14 -54.56(12) . . . . ?
C15 N1 C9 C14 145.54(8) . . . . ?
C16 C15 C20 C19 -1.15(14) . . . . ?
N1 C15 C20 C19 -179.71(8) . . . . ?
C19 C18 C17 C16 -0.49(14) . . . . ?
C15 C16 C17 C18 0.30(14) . . . . ?
C15 C20 C19 C18 0.97(14) . . . . ?
C17 C18 C19 C20 -0.15(15) . . . . ?
C7 C6 C2 O2 0.37(14) . . . . ?
C5 C6 C2 O2 -179.23(9) . . . . ?
C14 C9 C10 C11 1.50(13) . . . . ?
N1 C9 C10 C11 -177.98(8) . . . . ?
C13 C12 C11 C10 -1.49(14) . . . . ?
C9 C10 C11 C12 0.38(13) . . . . ?
C9 C14 C13 C12 1.16(14) . . . . ?
C11 C12 C13 C14 0.72(14) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_spa101_sq
_database_code_depnum_ccdc_archive 'CCDC 1485289'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-(diphenylamino)-2-ethoxybenzaldehyde '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7370(15)
_cell_length_b                   15.936(3)
_cell_length_c                   14.484(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.11(3)
_cell_angle_gamma                90
_cell_volume                     1739.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    36963
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15689
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.899
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4295
_reflns_number_gt                2810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4295
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46074(15) 0.53408(7) 0.75998(7) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.19902(13) 0.43122(6) 0.51647(6) 0.0264(3) Uani 1 1 d . . . . .
N1 N 0.29631(17) 0.67391(8) 0.33347(9) 0.0299(3) Uani 1 1 d . . . . .
C1 C 0.31631(19) 0.63186(9) 0.41930(10) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.24433(18) 0.55127(9) 0.42221(10) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.1817 0.5253 0.3654 0.029 Uiso 1 1 calc R U . . .
C3 C 0.26478(18) 0.50956(9) 0.50830(10) 0.0229(3) Uani 1 1 d . . . . .
C4 C 0.35649(18) 0.54748(9) 0.59342(9) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.42697(19) 0.62791(9) 0.58818(10) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.4890 0.6544 0.6448 0.032 Uiso 1 1 calc R U . . .
C6 C 0.40900(19) 0.66936(9) 0.50392(11) 0.0277(3) Uani 1 1 d . . . . .
H6 H 0.4592 0.7236 0.5026 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3794(2) 0.50546(10) 0.68413(10) 0.0296(3) Uani 1 1 d . . . . .
H7 H 0.3272 0.4516 0.6848 0.036 Uiso 1 1 calc R U . . .
C8 C 0.11220(19) 0.38906(9) 0.43039(10) 0.0269(3) Uani 1 1 d . . . . .
H8A H 0.1946 0.3836 0.3875 0.032 Uiso 1 1 calc R U . . .
H8B H 0.0074 0.4216 0.3973 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0559(2) 0.30364(10) 0.45665(12) 0.0360(4) Uani 1 1 d . . . . .
H9A H 0.1611 0.2707 0.4859 0.054 Uiso 1 1 calc R U . . .
H9B H -0.0095 0.2749 0.3995 0.054 Uiso 1 1 calc R U . . .
H9C H -0.0207 0.3096 0.5017 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3899(2) 0.75115(9) 0.32841(10) 0.0292(3) Uani 1 1 d . . . . .
C11 C 0.5700(2) 0.74987(10) 0.33121(12) 0.0366(4) Uani 1 1 d . . . . .
H11 H 0.6323 0.6981 0.3372 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6595(3) 0.82492(11) 0.32526(13) 0.0416(4) Uani 1 1 d . . . . .
H12 H 0.7826 0.8243 0.3261 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5691(3) 0.89989(11) 0.31819(11) 0.0399(4) Uani 1 1 d . . . . .
H13 H 0.6304 0.9511 0.3149 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3894(2) 0.90101(10) 0.31582(11) 0.0385(4) Uani 1 1 d . . . . .
H14 H 0.3278 0.9530 0.3108 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2988(2) 0.82668(10) 0.32078(10) 0.0333(4) Uani 1 1 d . . . . .
H15 H 0.1753 0.8275 0.3190 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1618(2) 0.65248(9) 0.25174(10) 0.0279(3) Uani 1 1 d . . . . .
C17 C 0.2089(2) 0.63729(10) 0.16635(11) 0.0365(4) Uani 1 1 d . . . . .
H17 H 0.3302 0.6390 0.1633 0.044 Uiso 1 1 calc R U . . .
C18 C 0.0791(3) 0.61958(11) 0.08536(12) 0.0459(5) Uani 1 1 d . . . . .
H18 H 0.1118 0.6093 0.0270 0.055 Uiso 1 1 calc R U . . .
C19 C -0.0965(3) 0.61685(12) 0.08945(12) 0.0489(5) Uani 1 1 d . . . . .
H19 H -0.1849 0.6043 0.0340 0.059 Uiso 1 1 calc R U . . .
C20 C -0.1448(2) 0.63232(12) 0.17399(12) 0.0431(4) Uani 1 1 d . . . . .
H20 H -0.2664 0.6306 0.1764 0.052 Uiso 1 1 calc R U . . .
C21 C -0.0163(2) 0.65042(10) 0.25559(11) 0.0328(4) Uani 1 1 d . . . . .
H21 H -0.0500 0.6613 0.3136 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2237(18) . ?
O2 C3 1.3634(18) . ?
O2 C8 1.4412(16) . ?
N1 C1 1.3897(18) . ?
N1 C16 1.4293(19) . ?
N1 C10 1.4383(19) . ?
C1 C2 1.404(2) . ?
C1 C6 1.405(2) . ?
C2 C3 1.3899(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4113(19) . ?
C4 C5 1.402(2) . ?
C4 C7 1.449(2) . ?
C5 C6 1.367(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.504(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.385(2) . ?
C10 C15 1.387(2) . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 C21 1.392(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.391(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C8 117.50(10) . . ?
C1 N1 C16 122.55(12) . . ?
C1 N1 C10 120.20(12) . . ?
C16 N1 C10 116.28(12) . . ?
N1 C1 C2 120.23(13) . . ?
N1 C1 C6 120.42(13) . . ?
C2 C1 C6 119.35(13) . . ?
C3 C2 C1 119.93(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O2 C3 C2 123.15(12) . . ?
O2 C3 C4 116.09(12) . . ?
C2 C3 C4 120.76(13) . . ?
C5 C4 C3 117.97(13) . . ?
C5 C4 C7 120.16(13) . . ?
C3 C4 C7 121.87(13) . . ?
C6 C5 C4 121.88(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.11(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C4 125.02(15) . . ?
O1 C7 H7 117.5 . . ?
C4 C7 H7 117.5 . . ?
O2 C8 C9 107.94(12) . . ?
O2 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
O2 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.33(14) . . ?
C11 C10 N1 120.04(13) . . ?
C15 C10 N1 119.63(14) . . ?
C10 C11 C12 119.74(15) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.88(17) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.26(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.33(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.46(16) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C21 119.61(15) . . ?
C17 C16 N1 119.39(14) . . ?
C21 C16 N1 120.93(14) . . ?
C16 C17 C18 120.16(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.17(16) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.09(16) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.39(18) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 119.58(16) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?

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
C16 N1 C1 C2 20.1(2) . . . . ?
C10 N1 C1 C2 -171.52(13) . . . . ?
C16 N1 C1 C6 -160.07(14) . . . . ?
C10 N1 C1 C6 8.3(2) . . . . ?
N1 C1 C2 C3 -179.99(13) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C8 O2 C3 C2 3.14(19) . . . . ?
C8 O2 C3 C4 -177.04(12) . . . . ?
C1 C2 C3 O2 -179.80(12) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
O2 C3 C4 C5 179.73(12) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
O2 C3 C4 C7 0.05(19) . . . . ?
C2 C3 C4 C7 179.87(13) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C7 C4 C5 C6 179.63(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
N1 C1 C6 C5 179.49(13) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C5 C4 C7 O1 -1.4(2) . . . . ?
C3 C4 C7 O1 178.26(14) . . . . ?
C3 O2 C8 C9 178.44(12) . . . . ?
C1 N1 C10 C11 75.11(19) . . . . ?
C16 N1 C10 C11 -115.81(16) . . . . ?
C1 N1 C10 C15 -104.87(17) . . . . ?
C16 N1 C10 C15 64.22(19) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
N1 C10 C11 C12 179.32(15) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
N1 C10 C15 C14 -179.94(13) . . . . ?
C13 C14 C15 C10 0.2(2) . . . . ?
C1 N1 C16 C17 -127.85(16) . . . . ?
C10 N1 C16 C17 63.35(19) . . . . ?
C1 N1 C16 C21 55.1(2) . . . . ?
C10 N1 C16 C21 -113.67(16) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
N1 C16 C17 C18 -177.50(14) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 -0.3(2) . . . . ?
C17 C16 C21 C20 0.7(2) . . . . ?
N1 C16 C21 C20 177.67(14) . . . . ?

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.054



