# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1440658'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(2-(hydroxymethyl)phenyl)-2-naphthamide
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         277.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1207(5)
_cell_length_b                   7.6201(5)
_cell_length_c                   25.3427(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.9930(10)
_cell_angle_gamma                90
_cell_volume                     1364.88(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    15318
_cell_measurement_theta_min      2.7865
_cell_measurement_theta_max      33.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   'SADABS-2012/1, G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18157
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3287
_reflns_number_gt                3132
_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT v.8.34A, Bruker-AXS'
_computing_data_reduction        'SAINT v.8.34A, Bruker-AXS'
_computing_structure_solution    'SHELXT-Version 2013/1, G. Sheldrick'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L. Barbour (1999)'
_computing_publication_material  ?
_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)+(0.0596P)²+0.5057P] 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         3287
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_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 0.16170(10) 0.70965(11) 0.56210(3) 0.01812(18) Uani 1 1 d . . . . .
O2 O 0.81349(10) 0.66852(10) 0.50529(3) 0.01663(17) Uani 1 1 d . . . . .
H2 H 0.9158 0.6754 0.5239 0.020 Uiso 1 1 calc R U . . .
N1 N 0.44525(11) 0.67158(11) 0.52934(3) 0.01219(18) Uani 1 1 d . . . . .
H1 H 0.5571 0.6295 0.5376 0.015 Uiso 1 1 calc R U . . .
C11 C 0.32798(13) 0.66054(13) 0.56734(4) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.40655(13) 0.74394(13) 0.47764(4) 0.01189(19) Uani 1 1 d . . . . .
C10 C 0.41718(13) 0.58776(13) 0.61935(4) 0.01258(19) Uani 1 1 d . . . . .
C8 C 0.68025(13) 0.56148(13) 0.68952(4) 0.0130(2) Uani 1 1 d . . . . .
C9 C 0.60418(13) 0.61790(13) 0.63795(4) 0.01264(19) Uani 1 1 d . . . . .
H9 H 0.6814 0.6758 0.6165 0.015 Uiso 1 1 calc R U . . .
C13 C 0.55826(14) 0.82651(13) 0.45682(4) 0.0132(2) Uani 1 1 d . . . . .
C3 C 0.56222(14) 0.46930(13) 0.72153(4) 0.0143(2) Uani 1 1 d . . . . .
C17 C 0.22965(14) 0.72924(13) 0.44756(4) 0.0138(2) Uani 1 1 d . . . . .
H17 H 0.1312 0.6716 0.4613 0.017 Uiso 1 1 calc R U . . .
C7 C 0.86969(14) 0.59988(14) 0.71043(4) 0.0164(2) Uani 1 1 d . . . . .
H7 H 0.9483 0.6581 0.6895 0.020 Uiso 1 1 calc R U . . .
C1 C 0.30034(14) 0.49476(14) 0.65133(4) 0.0156(2) Uani 1 1 d . . . . .
H1A H 0.1742 0.4743 0.6386 0.019 Uiso 1 1 calc R U . . .
C16 C 0.20219(14) 0.80183(14) 0.39676(4) 0.0168(2) Uani 1 1 d . . . . .
H16 H 0.0841 0.7941 0.3767 0.020 Uiso 1 1 calc R U . . .
C18 C 0.74937(14) 0.84117(13) 0.48932(4) 0.0152(2) Uani 1 1 d . . . . .
H18A H 0.8386 0.8958 0.4684 0.018 Uiso 1 1 calc R U . . .
H18B H 0.7402 0.9133 0.5204 0.018 Uiso 1 1 calc R U . . .
C15 C 0.34992(15) 0.88575(15) 0.37577(4) 0.0188(2) Uani 1 1 d . . . . .
H15 H 0.3306 0.9345 0.3419 0.023 Uiso 1 1 calc R U . . .
C2 C 0.37141(15) 0.43487(14) 0.70069(4) 0.0165(2) Uani 1 1 d . . . . .
H2A H 0.2942 0.3711 0.7207 0.020 Uiso 1 1 calc R U . . .
C14 C 0.52704(14) 0.89632(14) 0.40577(4) 0.0167(2) Uani 1 1 d . . . . .
H14 H 0.6261 0.9510 0.3914 0.020 Uiso 1 1 calc R U . . .
C4 C 0.63855(16) 0.41853(14) 0.77371(4) 0.0177(2) Uani 1 1 d . . . . .
H4 H 0.5638 0.3562 0.7948 0.021 Uiso 1 1 calc R U . . .
C5 C 0.82082(16) 0.46031(15) 0.79329(4) 0.0202(2) Uani 1 1 d . . . . .
H5 H 0.8679 0.4284 0.8278 0.024 Uiso 1 1 calc R U . . .
C6 C 0.93795(15) 0.55169(16) 0.76137(4) 0.0204(2) Uani 1 1 d . . . . .
H6 H 1.0617 0.5792 0.7749 0.024 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 C11 1.2334(12) . ?
O2 C18 1.4346(12) . ?
O2 H2 0.8200 . ?
N1 C11 1.3519(12) . ?
N1 C12 1.4174(12) . ?
N1 H1 0.8600 . ?
C11 C10 1.4981(13) . ?
C12 C17 1.3952(13) . ?
C12 C13 1.4072(13) . ?
C10 C9 1.3767(13) . ?
C10 C1 1.4196(13) . ?
C8 C7 1.4184(13) . ?
C8 C3 1.4227(13) . ?
C8 C9 1.4189(13) . ?
C9 H9 0.9300 . ?
C13 C14 1.3914(14) . ?
C13 C18 1.5066(13) . ?
C3 C4 1.4209(13) . ?
C3 C2 1.4209(14) . ?
C17 C16 1.3929(14) . ?
C17 H17 0.9300 . ?
C7 C6 1.3731(14) . ?
C7 H7 0.9300 . ?
C1 C2 1.3692(14) . ?
C1 H1A 0.9300 . ?
C16 C15 1.3909(15) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C15 C14 1.3934(14) . ?
C15 H15 0.9300 . ?
C2 H2A 0.9300 . ?
C14 H14 0.9300 . ?
C4 C5 1.3694(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.4139(16) . ?
C5 H5 0.9300 . ?
C6 H6 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
C18 O2 H2 109.5 . . ?
C11 N1 C12 127.98(8) . . ?
C11 N1 H1 116.0 . . ?
C12 N1 H1 116.0 . . ?
O1 C11 N1 124.92(9) . . ?
O1 C11 C10 120.38(9) . . ?
N1 C11 C10 114.66(8) . . ?
C17 C12 C13 120.95(9) . . ?
C17 C12 N1 122.33(9) . . ?
C13 C12 N1 116.67(8) . . ?
C9 C10 C1 119.83(9) . . ?
C9 C10 C11 121.89(9) . . ?
C1 C10 C11 118.16(9) . . ?
C7 C8 C3 119.32(9) . . ?
C7 C8 C9 121.37(9) . . ?
C3 C8 C9 119.28(9) . . ?
C10 C9 C8 120.64(9) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C14 C13 C12 118.46(9) . . ?
C14 C13 C18 120.76(9) . . ?
C12 C13 C18 120.78(9) . . ?
C4 C3 C8 118.66(9) . . ?
C4 C3 C2 122.40(9) . . ?
C8 C3 C2 118.93(9) . . ?
C16 C17 C12 119.27(9) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C6 C7 C8 120.52(10) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C2 C1 C10 120.72(9) . . ?
C2 C1 H1A 119.6 . . ?
C10 C1 H1A 119.6 . . ?
C15 C16 C17 120.56(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
O2 C18 C13 108.75(8) . . ?
O2 C18 H18A 109.9 . . ?
C13 C18 H18A 109.9 . . ?
O2 C18 H18B 109.9 . . ?
C13 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C14 C15 C16 119.62(9) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C1 C2 C3 120.56(9) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C15 C14 C13 121.12(9) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C5 C4 C3 120.81(10) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.42(9) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.24(10) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration unk



#===END
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1440659'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(R)-N-(2-(((1-(Naphthalen-2-yl)ethyl)imino)methyl)phenyl)-2-naphthamide
_chemical_name_common            ?
_chemical_formula_moiety         'C30 H24 N2 O'
_chemical_formula_sum            'C30 H24 N2 O'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         428.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.8608(11)
_cell_length_b                   13.688(3)
_cell_length_c                   27.498(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2206.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9636
_cell_measurement_theta_min      2.665
_cell_measurement_theta_max      31.5145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5547
_exptl_absorpt_correction_T_max  0.7296
_exptl_absorpt_process_details   'SADABS-2012/1, G.Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   
;sealed X-ray tube
;
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31611
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.481
_diffrn_reflns_theta_max         31.798
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7379
_reflns_number_gt                5568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.993

_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT v.834A, Bruker-AXS'
_computing_data_reduction        'SAINT v.834A, Bruker-AXS'
_computing_structure_solution    'SHELXT-2013/1, G.Sheldrick'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999)'
_computing_publication_material  ?
_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)+(0.0845P)²+10.3641P] 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_abs_structure_details 
;
 Flack x determined using 1612 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7379
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.1288
_refine_ls_wR_factor_ref         0.3111
_refine_ls_wR_factor_gt          0.2958
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
C3 C 0.4358(10) 0.3606(5) 0.8858(2) 0.0165(11) Uani 1 1 d . . . . .
C7 C 0.8013(9) 0.4191(5) 0.9212(2) 0.0182(11) Uani 1 1 d . . . . .
H7 H 0.9417 0.4501 0.9180 0.022 Uiso 1 1 calc R U . . .
C27 C 1.1597(10) 0.5912(5) 0.9754(2) 0.0198(12) Uani 1 1 d . . . . .
C9 C 0.7061(10) 0.4539(5) 0.8349(2) 0.0182(11) Uani 1 1 d . . . . .
H9 H 0.8420 0.4883 0.8314 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6508(10) 0.4122(5) 0.8803(2) 0.0188(11) Uani 1 1 d . . . . .
C23 C 0.7963(10) 0.6468(5) 1.0096(2) 0.0202(12) Uani 1 1 d . . . . .
H23 H 0.6597 0.6808 1.0063 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3815(9) 0.3212(5) 0.9314(2) 0.0174(11) Uani 1 1 d . . . . .
H4 H 0.2438 0.2883 0.9354 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5608(10) 0.4444(5) 0.7952(2) 0.0189(11) Uani 1 1 d . . . . .
C2 C 0.2916(10) 0.3541(5) 0.8445(2) 0.0189(11) Uani 1 1 d . . . . .
H2 H 0.1515 0.3228 0.8474 0.023 Uiso 1 1 calc R U . . .
C17 C 1.0805(12) 0.6536(5) 0.7131(3) 0.0258(14) Uani 1 1 d . . . . .
C26 C 1.2019(11) 0.5426(5) 1.0203(2) 0.0239(13) Uani 1 1 d . . . . .
H26 H 1.3348 0.5062 1.0238 0.029 Uiso 1 1 calc R U . . .
C24 C 0.8445(12) 0.6006(5) 1.0529(2) 0.0249(13) Uani 1 1 d . . . . .
H24 H 0.7412 0.6040 1.0785 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5278(10) 0.3300(5) 0.9705(2) 0.0198(12) Uani 1 1 d . . . . .
H5 H 0.4877 0.3030 1.0003 0.024 Uiso 1 1 calc R U . . .
C22 C 0.9510(10) 0.6437(5) 0.9699(2) 0.0175(11) Uani 1 1 d . . . . .
N2 N 1.0074(10) 0.6863(5) 0.8001(2) 0.0253(12) Uani 1 1 d . . . . .
C1 C 0.3517(10) 0.3923(5) 0.8008(2) 0.0214(12) Uani 1 1 d . . . . .
H1 H 0.2554 0.3844 0.7743 0.026 Uiso 1 1 calc R U . . .
C28 C 1.3189(11) 0.5871(5) 0.9372(2) 0.0237(13) Uani 1 1 d . . . . .
H28 H 1.4536 0.5521 0.9410 0.028 Uiso 1 1 calc R U . . .
C29 C 1.2765(11) 0.6340(5) 0.8948(3) 0.0234(13) Uani 1 1 d . . . . .
H29 H 1.3812 0.6286 0.8696 0.028 Uiso 1 1 calc R U . . .
C15 C 1.1649(11) 0.6585(5) 0.6260(3) 0.0266(14) Uani 1 1 d . . . . .
H15 H 1.2577 0.6786 0.6004 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8929(10) 0.5910(5) 0.7037(2) 0.0191(11) Uani 1 1 d . . . . .
C21 C 0.9149(13) 0.6941(5) 0.9251(2) 0.0263(14) Uani 1 1 d . . . . .
H21 H 0.7811 0.7295 0.9207 0.032 Uiso 1 1 calc R U . . .
N1 N 0.7705(9) 0.5568(5) 0.74425(18) 0.0234(11) Uani 1 1 d . . . . .
H1A H 0.7893 0.5884 0.7710 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9742(12) 0.6014(5) 0.6173(2) 0.0252(13) Uani 1 1 d . . . . .
H14 H 0.9344 0.5855 0.5856 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7375(10) 0.3796(5) 0.9656(2) 0.0197(12) Uani 1 1 d . . . . .
H6 H 0.8336 0.3857 0.9923 0.024 Uiso 1 1 calc R U . . .
O1 O 0.5551(10) 0.4366(5) 0.70899(18) 0.0375(14) Uani 1 1 d . . . . .
C16 C 1.2156(11) 0.6856(5) 0.6738(2) 0.0245(13) Uani 1 1 d . . . . .
H16 H 1.3410 0.7254 0.6798 0.029 Uiso 1 1 calc R U . . .
C13 C 0.8415(11) 0.5677(5) 0.6559(2) 0.0221(12) Uani 1 1 d . . . . .
H13 H 0.7154 0.5286 0.6494 0.027 Uiso 1 1 calc R U . . .
C25 C 1.0506(12) 0.5480(5) 1.0586(2) 0.0251(13) Uani 1 1 d . . . . .
H25 H 1.0837 0.5174 1.0879 0.030 Uiso 1 1 calc R U . . .
C19 C 1.0537(11) 0.7506(6) 0.8419(2) 0.0247(13) Uani 1 1 d . . . . .
H19 H 1.1986 0.7843 0.8361 0.030 Uiso 1 1 calc R U . . .
C20 C 1.0765(11) 0.6914(5) 0.8878(2) 0.0221(12) Uani 1 1 d . . . . .
C11 C 0.6239(11) 0.4783(5) 0.7458(2) 0.0244(13) Uani 1 1 d . . . . .
C18 C 1.1256(11) 0.7003(5) 0.7613(2) 0.0236(13) Uani 1 1 d . . . . .
H18 H 1.2489 0.7429 0.7633 0.028 Uiso 1 1 calc R U . . .
C30 C 0.8635(14) 0.8270(6) 0.8433(3) 0.0319(16) Uani 1 1 d . . . . .
H30A H 0.7180 0.7949 0.8421 0.048 Uiso 1 1 calc R U . . .
H30B H 0.8784 0.8700 0.8159 0.048 Uiso 1 1 calc R U . . .
H30C H 0.8748 0.8642 0.8728 0.048 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
C3 C4 1.400(8) . ?
C3 C2 1.419(8) . ?
C3 C8 1.453(8) . ?
C7 C6 1.387(9) . ?
C7 C8 1.431(8) . ?
C7 H7 0.9300 . ?
C27 C28 1.406(9) . ?
C27 C22 1.427(8) . ?
C27 C26 1.424(9) . ?
C9 C10 1.390(8) . ?
C9 C8 1.412(8) . ?
C9 H9 0.9300 . ?
C23 C24 1.378(10) . ?
C23 C22 1.419(8) . ?
C23 H23 0.9300 . ?
C4 C5 1.380(9) . ?
C4 H4 0.9300 . ?
C10 C1 1.427(8) . ?
C10 C11 1.483(9) . ?
C2 C1 1.355(9) . ?
C2 H2 0.9300 . ?
C17 C16 1.410(9) . ?
C17 C12 1.417(9) . ?
C17 C18 1.493(10) . ?
C26 C25 1.379(10) . ?
C26 H26 0.9300 . ?
C24 C25 1.415(10) . ?
C24 H24 0.9300 . ?
C5 C6 1.410(8) . ?
C5 H5 0.9300 . ?
C22 C21 1.428(9) . ?
N2 C18 1.288(9) . ?
N2 C19 1.472(9) . ?
C1 H1 0.9300 . ?
C28 C29 1.352(10) . ?
C28 H28 0.9300 . ?
C29 C20 1.424(9) . ?
C29 H29 0.9300 . ?
C15 C14 1.384(10) . ?
C15 C16 1.399(10) . ?
C15 H15 0.9300 . ?
C12 C13 1.385(9) . ?
C12 N1 1.406(7) . ?
C21 C20 1.397(10) . ?
C21 H21 0.9300 . ?
N1 C11 1.378(8) . ?
N1 H1A 0.8600 . ?
C14 C13 1.395(9) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
O1 C11 1.229(8) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C25 H25 0.9300 . ?
C19 C20 1.505(10) . ?
C19 C30 1.530(10) . ?
C19 H19 0.9800 . ?
C18 H18 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C2 123.9(6) . . ?
C4 C3 C8 118.5(5) . . ?
C2 C3 C8 117.6(5) . . ?
C6 C7 C8 119.9(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C28 C27 C22 120.7(6) . . ?
C28 C27 C26 120.9(6) . . ?
C22 C27 C26 118.4(5) . . ?
C10 C9 C8 121.1(5) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C8 C7 121.8(6) . . ?
C9 C8 C3 119.2(5) . . ?
C7 C8 C3 119.0(5) . . ?
C24 C23 C22 121.2(6) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C5 C4 C3 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C9 C10 C1 119.2(5) . . ?
C9 C10 C11 122.5(5) . . ?
C1 C10 C11 118.1(5) . . ?
C1 C2 C3 122.1(5) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C16 C17 C12 118.9(6) . . ?
C16 C17 C18 116.5(6) . . ?
C12 C17 C18 124.0(6) . . ?
C25 C26 C27 121.7(6) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C23 C24 C25 120.3(6) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C23 C22 C27 118.8(6) . . ?
C23 C22 C21 123.6(6) . . ?
C27 C22 C21 117.5(6) . . ?
C18 N2 C19 117.4(6) . . ?
C2 C1 C10 120.8(6) . . ?
C2 C1 H1 119.6 . . ?
C10 C1 H1 119.6 . . ?
C29 C28 C27 120.2(6) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C20 122.0(6) . . ?
C28 C29 H29 119.0 . . ?
C20 C29 H29 119.0 . . ?
C14 C15 C16 118.9(6) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C13 C12 N1 124.4(6) . . ?
C13 C12 C17 118.8(6) . . ?
N1 C12 C17 116.8(6) . . ?
C20 C21 C22 121.4(7) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C11 N1 C12 127.0(6) . . ?
C11 N1 H1A 116.5 . . ?
C12 N1 H1A 116.5 . . ?
C15 C14 C13 120.4(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C7 C6 C5 120.4(6) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C17 C16 C15 121.3(6) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C12 C13 C14 121.6(6) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C26 C25 C24 119.5(6) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N2 C19 C20 110.4(6) . . ?
N2 C19 C30 107.1(6) . . ?
C20 C19 C30 114.4(6) . . ?
N2 C19 H19 108.3 . . ?
C20 C19 H19 108.3 . . ?
C30 C19 H19 108.3 . . ?
C21 C20 C29 118.2(6) . . ?
C21 C20 C19 122.8(6) . . ?
C29 C20 C19 118.9(6) . . ?
O1 C11 N1 122.8(6) . . ?
O1 C11 C10 121.8(6) . . ?
N1 C11 C10 115.3(5) . . ?
N2 C18 C17 125.2(6) . . ?
N2 C18 H18 117.4 . . ?
C17 C18 H18 117.4 . . ?
C19 C30 H30A 109.5 . . ?
C19 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C19 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.661
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.120




#===END
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1440660'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        N-(2-formylphenyl)-2-naphthamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   24.4271(14)
_cell_length_b                   3.7892(3)
_cell_length_c                   14.3031(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1323.88(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3662
_cell_measurement_theta_min      2.853
_cell_measurement_theta_max      25.337

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5634
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2012/1,G. Sheldrick'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10296
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.667
_diffrn_reflns_theta_max         25.296
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2423
_reflns_number_gt                2148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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       'APEX 2, Bruker-AXS'
_computing_cell_refinement       'SAINT v. 8.34A, Bruker-AXS'
_computing_data_reduction        'SAINT v. 8.34A, Bruker-AXS'
_computing_structure_solution    'SHELXT-Version 2013/1, G.Sheldrick'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999)'
_computing_publication_material  ?
_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)+(0.0549P)²+0.1559P] 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_abs_structure_details 
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2423
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.45850(9) 0.4383(6) 0.62124(14) 0.0280(6) Uani 1 1 d . . . . .
O2 O 0.42656(10) 0.3422(7) 0.27989(16) 0.0367(6) Uani 1 1 d . . . . .
N1 N 0.45244(10) 0.3879(7) 0.46229(17) 0.0207(6) Uani 1 1 d . . . . .
H19 H 0.4313 0.4304 0.4156 0.025 Uiso 1 1 calc R U . . .
C1 C 0.34898(12) 0.7526(8) 0.4660(2) 0.0229(7) Uani 1 1 d . . . . .
H1 H 0.3672 0.7477 0.4089 0.028 Uiso 1 1 calc R U . . .
C2 C 0.29634(13) 0.8780(8) 0.4708(2) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.2791 0.9557 0.4165 0.029 Uiso 1 1 calc R U . . .
C3 C 0.26786(12) 0.8909(8) 0.5567(2) 0.0225(7) Uani 1 1 d . . . . .
C4 C 0.21258(13) 1.0148(9) 0.5632(2) 0.0265(7) Uani 1 1 d . . . . .
H4 H 0.1946 1.0932 0.5098 0.032 Uiso 1 1 calc R U . . .
C5 C 0.18639(13) 1.0183(9) 0.6470(2) 0.0279(7) Uani 1 1 d . . . . .
H5 H 0.1504 1.0983 0.6504 0.033 Uiso 1 1 calc R U . . .
C6 C 0.21305(13) 0.9020(9) 0.7292(2) 0.0282(8) Uani 1 1 d . . . . .
H6 H 0.1946 0.9054 0.7860 0.034 Uiso 1 1 calc R U . . .
C7 C 0.26612(13) 0.7842(9) 0.7253(2) 0.0253(7) Uani 1 1 d . . . . .
H7 H 0.2836 0.7098 0.7796 0.030 Uiso 1 1 calc R U . . .
C8 C 0.29417(12) 0.7761(8) 0.6388(2) 0.0215(7) Uani 1 1 d . . . . .
C9 C 0.34874(12) 0.6452(8) 0.6317(2) 0.0228(7) Uani 1 1 d . . . . .
H9 H 0.3664 0.5677 0.6855 0.027 Uiso 1 1 calc R U . . .
C10 C 0.37589(12) 0.6301(8) 0.5482(2) 0.0217(6) Uani 1 1 d . . . . .
C11 C 0.43242(12) 0.4810(8) 0.5482(2) 0.0214(6) Uani 1 1 d . . . . .
C12 C 0.50277(12) 0.2328(8) 0.4405(2) 0.0197(6) Uani 1 1 d . . . . .
C13 C 0.54375(12) 0.1635(8) 0.5057(2) 0.0216(7) Uani 1 1 d . . . . .
H13 H 0.5387 0.2230 0.5682 0.026 Uiso 1 1 calc R U . . .
C14 C 0.59212(13) 0.0051(8) 0.4768(2) 0.0245(7) Uani 1 1 d . . . . .
H14 H 0.6190 -0.0454 0.5210 0.029 Uiso 1 1 calc R U . . .
C15 C 0.60150(14) -0.0800(8) 0.3835(2) 0.0270(7) Uani 1 1 d . . . . .
H15 H 0.6346 -0.1800 0.3652 0.032 Uiso 1 1 calc R U . . .
C16 C 0.56112(13) -0.0141(9) 0.3189(2) 0.0261(7) Uani 1 1 d . . . . .
H16 H 0.5669 -0.0728 0.2565 0.031 Uiso 1 1 calc R U . . .
C17 C 0.51108(12) 0.1410(8) 0.3456(2) 0.0211(7) Uani 1 1 d . . . . .
C18 C 0.47093(14) 0.1992(9) 0.2713(2) 0.0285(8) Uani 1 1 d . . . . .
H18 H 0.4801 0.1194 0.2118 0.034 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 C11 1.235(4) . ?
O2 C18 1.218(4) . ?
N1 C11 1.368(4) . ?
N1 C12 1.398(4) . ?
N1 H19 0.8600 . ?
C1 C2 1.372(4) . ?
C1 C10 1.425(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.414(4) . ?
C2 H2 0.9300 . ?
C3 C8 1.407(4) . ?
C3 C4 1.433(5) . ?
C4 C5 1.359(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.415(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.426(4) . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.492(4) . ?
C12 C13 1.393(4) . ?
C12 C17 1.416(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.409(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.463(5) . ?
C18 H18 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
C11 N1 C12 128.6(3) . . ?
C11 N1 H19 115.7 . . ?
C12 N1 H19 115.7 . . ?
C2 C1 C10 120.3(3) . . ?
C2 C1 H1 119.9 . . ?
C10 C1 H1 119.9 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C8 C3 C2 119.3(3) . . ?
C8 C3 C4 118.6(3) . . ?
C2 C3 C4 122.1(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 120.1(3) . . ?
C3 C8 C9 118.4(3) . . ?
C7 C8 C9 121.5(3) . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C1 118.9(3) . . ?
C9 C10 C11 117.7(3) . . ?
C1 C10 C11 123.4(3) . . ?
O1 C11 N1 122.8(3) . . ?
O1 C11 C10 121.8(3) . . ?
N1 C11 C10 115.4(3) . . ?
C13 C12 N1 124.2(3) . . ?
C13 C12 C17 119.5(3) . . ?
N1 C12 C17 116.3(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.1(3) . . ?
C16 C17 C18 116.6(3) . . ?
C12 C17 C18 124.3(3) . . ?
O2 C18 C17 126.2(3) . . ?
O2 C18 H18 116.9 . . ?
C17 C18 H18 116.9 . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040




#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
