# 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_RA102_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 997579'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-(3-methylphenyl)-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31


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                   26.362(2)
_cell_length_b                   5.8842(5)
_cell_length_c                   8.6253(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.291(5)
_cell_angle_gamma                90
_cell_volume                     1336.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    4553
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      31.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7414
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22348
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         33.156
_diffrn_reflns_theta_full        31.500
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4687
_reflns_number_gt                3578
_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010)
;


_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)+(0.1030P)²+3.0892P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4687
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.2550
_refine_ls_wR_factor_gt          0.2443
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.005
_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
C1 C 0.31015(8) 0.3227(4) 0.8238(2) 0.0140(4) Uani 1 1 d . . . . .
H1 H 0.2965 0.1801 0.7914 0.017 Uiso 1 1 calc R U . . .
C2 C 0.28299(8) 0.4589(4) 0.9203(2) 0.0137(4) Uani 1 1 d . . . . .
C3 C 0.30273(9) 0.6751(4) 0.9674(3) 0.0160(4) Uani 1 1 d . . . . .
H3 H 0.2839 0.7694 1.0336 0.019 Uiso 1 1 calc R U . . .
C4 C 0.34883(9) 0.7471(4) 0.9171(3) 0.0156(4) Uani 1 1 d . . . . .
H4 H 0.3614 0.8923 0.9478 0.019 Uiso 1 1 calc R U . . .
C5 C 0.42662(8) 0.6735(4) 0.7702(3) 0.0173(4) Uani 1 1 d . . . . .
H5 H 0.4403 0.8165 0.8014 0.021 Uiso 1 1 calc R U . . .
C6 C 0.45408(9) 0.5341(4) 0.6779(3) 0.0191(4) Uani 1 1 d . . . . .
H6 H 0.4866 0.5805 0.6466 0.023 Uiso 1 1 calc R U . . .
C7 C 0.43415(9) 0.3206(4) 0.6287(3) 0.0180(4) Uani 1 1 d . . . . .
H7 H 0.4532 0.2255 0.5636 0.022 Uiso 1 1 calc R U . . .
C8 C 0.38733(8) 0.2514(4) 0.6752(3) 0.0163(4) Uani 1 1 d . . . . .
H8 H 0.3743 0.1079 0.6424 0.020 Uiso 1 1 calc R U . . .
C9 C 0.35815(8) 0.3921(4) 0.7719(2) 0.0138(4) Uani 1 1 d . . . . .
C10 C 0.37800(8) 0.6073(4) 0.8198(3) 0.0147(4) Uani 1 1 d . . . . .
C21 C 0.23526(8) 0.3818(4) 0.9942(2) 0.0142(4) Uani 1 1 d . . . . .
O1 O 0.22402(6) 0.4645(3) 1.12060(19) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.20790(7) 0.2195(3) 0.9189(2) 0.0166(4) Uani 1 1 d . . . . .
H1N H 0.2171(11) 0.176(6) 0.821(4) 0.020 Uiso 1 1 d . U . . .
C11 C 0.16330(8) 0.1107(4) 0.9700(2) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.13001(8) 0.2134(4) 1.0701(3) 0.0154(4) Uani 1 1 d . . . . .
H12 H 0.1377 0.3589 1.1126 0.018 Uiso 1 1 calc R U . . .
C13 C 0.08523(8) 0.1028(4) 1.1083(3) 0.0163(4) Uani 1 1 d . . . . .
C131 C 0.04806(9) 0.2209(4) 1.2100(3) 0.0215(5) Uani 1 1 d . . . . .
H13A H 0.0177 0.2642 1.1474 0.032 Uiso 1 1 calc R U . . .
H13B H 0.0639 0.3574 1.2555 0.032 Uiso 1 1 calc R U . . .
H13C H 0.0384 0.1179 1.2931 0.032 Uiso 1 1 calc R U . . .
C14 C 0.07487(9) -0.1131(4) 1.0477(3) 0.0187(4) Uani 1 1 d . . . . .
H14 H 0.0449 -0.1909 1.0749 0.022 Uiso 1 1 calc R U . . .
C15 C 0.10815(10) -0.2144(4) 0.9478(3) 0.0207(5) Uani 1 1 d . . . . .
H15 H 0.1006 -0.3607 0.9065 0.025 Uiso 1 1 calc R U . . .
C16 C 0.15237(9) -0.1048(4) 0.9075(3) 0.0183(4) Uani 1 1 d . . . . .
H16 H 0.1749 -0.1747 0.8387 0.022 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
C1 C2 1.377(3) . ?
C1 C9 1.419(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.427(3) . ?
C2 C21 1.503(3) . y
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C10 1.423(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(3) . ?
C5 C10 1.422(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.425(3) . ?
C21 O1 1.240(3) . y
C21 N1 1.348(3) . y
N1 C11 1.424(3) . y
N1 H1N 0.93(3) . y
C11 C12 1.394(3) . ?
C11 C16 1.403(3) . ?
C12 C13 1.399(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(3) . ?
C13 C131 1.510(3) . y
C131 H13A 0.9800 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 C1 C9 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
C9 C1 H1 119.5 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 C21 123.02(19) . . ?
C3 C2 C21 116.77(19) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C6 C5 C10 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C1 C9 C8 121.8(2) . . ?
C1 C9 C10 119.10(19) . . ?
C8 C9 C10 119.07(19) . . ?
C5 C10 C4 122.3(2) . . ?
C5 C10 C9 118.8(2) . . ?
C4 C10 C9 118.93(19) . . ?
O1 C21 N1 124.0(2) . . y
O1 C21 C2 119.21(19) . . y
N1 C21 C2 116.76(18) . . y
C21 N1 C11 127.01(19) . . y
C21 N1 H1N 119(2) . . ?
C11 N1 H1N 114(2) . . ?
C12 C11 C16 120.3(2) . . ?
C12 C11 N1 123.0(2) . . y
C16 C11 N1 116.6(2) . . y
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 C131 121.0(2) . . y
C12 C13 C131 119.7(2) . . y
C13 C131 H13A 109.5 . . ?
C13 C131 H13B 109.5 . . ?
H13A C131 H13B 109.5 . . ?
C13 C131 H13C 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 119.0(2) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 1.1(3) . . . . ?
C9 C1 C2 C21 -172.19(19) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C21 C2 C3 C4 173.4(2) . . . . ?
C2 C3 C4 C10 -1.0(3) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C2 C1 C9 C8 178.5(2) . . . . ?
C2 C1 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C1 -178.8(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C6 C5 C10 C4 179.2(2) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C3 C4 C10 C5 -177.8(2) . . . . ?
C3 C4 C10 C9 1.4(3) . . . . ?
C1 C9 C10 C5 178.6(2) . . . . ?
C8 C9 C10 C5 -0.5(3) . . . . ?
C1 C9 C10 C4 -0.5(3) . . . . ?
C8 C9 C10 C4 -179.7(2) . . . . ?
C1 C2 C21 O1 151.3(2) . . . . ?
C3 C2 C21 O1 -22.1(3) . . . . ?
C1 C2 C21 N1 -26.8(3) . . . . y
C3 C2 C21 N1 159.7(2) . . . . y
O1 C21 N1 C11 -1.9(4) . . . . y
C2 C21 N1 C11 176.1(2) . . . . y
C21 N1 C11 C12 27.1(4) . . . . y
C21 N1 C11 C16 -156.3(2) . . . . y
C16 C11 C12 C13 -0.4(3) . . . . ?
N1 C11 C12 C13 176.1(2) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C11 C12 C13 C131 -176.7(2) . . . . y
C12 C13 C14 C15 -1.4(3) . . . . ?
C131 C13 C14 C15 176.6(2) . . . . y
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
N1 C11 C16 C15 -177.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.93(3) 1.93(3) 2.839(3) 167(3) 4_565
C1 H1 O1 0.95 2.52 3.281(3) 138 4_565
C16 H16 O1 0.95 2.63 3.278(3) 126 4_565
C4 H4 Cg2 0.95 2.77 3.449(3) 131 4_565
C8 H8 Cg1 0.95 2.73 3.421(3) 132 4_554
C131 H13B Cg3 0.98 2.69 3.530(3) 146 4_555

_iucr_geom_hbonds_special_details 
;
Cg1, Cg2 and Cg3 are the centroids of the C1...C4,C9,C10; C5...C10 and 
C11...C16 rings respectively
;
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_RA105_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 997577'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-phenyl-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   28.7372(16)
_cell_length_b                   5.4797(3)
_cell_length_c                   7.8381(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.767(3)
_cell_angle_gamma                90
_cell_volume                     1193.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    2651
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      31.46


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7968
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10441
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.321
_diffrn_reflns_theta_max         31.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.906
_reflns_number_total             3533
_reflns_number_gt                3049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.719
_reflns_Friedel_fraction_full    0.814

_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2013 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009), PublCIF (Westrip 2010)
;


_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)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.6(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3533
_refine_ls_number_parameters     175
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.48153(7) 0.4488(4) 0.3857(3) 0.0128(4) Uani 1 1 d . . . . .
H1 H 0.4865 0.5996 0.3331 0.015 Uiso 1 1 calc R U . . .
C2 C 0.52074(7) 0.3079(4) 0.4682(3) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.51353(7) 0.0856(4) 0.5509(3) 0.0153(4) Uani 1 1 d . . . . .
H3 H 0.5404 -0.0104 0.6090 0.018 Uiso 1 1 calc R U . . .
C4 C 0.46761(7) 0.0086(4) 0.5474(3) 0.0149(4) Uani 1 1 d . . . . .
H4 H 0.4633 -0.1392 0.6047 0.018 Uiso 1 1 calc R U . . .
C5 C 0.37908(7) 0.0675(4) 0.4509(3) 0.0148(4) Uani 1 1 d . . . . .
H5 H 0.3740 -0.0808 0.5062 0.018 Uiso 1 1 calc R U . . .
C6 C 0.34047(7) 0.2041(4) 0.3634(3) 0.0167(4) Uani 1 1 d . . . . .
H6 H 0.3087 0.1489 0.3572 0.020 Uiso 1 1 calc R U . . .
C7 C 0.34750(7) 0.4267(4) 0.2821(3) 0.0168(4) Uani 1 1 d . . . . .
H7 H 0.3205 0.5200 0.2214 0.020 Uiso 1 1 calc R U . . .
C8 C 0.39319(7) 0.5089(4) 0.2904(3) 0.0147(4) Uani 1 1 d . . . . .
H8 H 0.3975 0.6594 0.2364 0.018 Uiso 1 1 calc R U . . .
C9 C 0.43396(7) 0.3708(4) 0.3789(3) 0.0118(4) Uani 1 1 d . . . . .
C10 C 0.42684(7) 0.1464(4) 0.4596(3) 0.0125(4) Uani 1 1 d . . . . .
C21 C 0.56977(7) 0.3941(4) 0.4614(3) 0.0143(4) Uani 1 1 d . . . . .
O1 O 0.57957(6) 0.6108(3) 0.4515(2) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.60174(6) 0.2082(3) 0.4619(2) 0.0147(3) Uani 1 1 d . . . . .
H1N H 0.5903(10) 0.065(5) 0.455(4) 0.018 Uiso 1 1 d . U . . .
C11 C 0.64998(7) 0.2332(4) 0.4517(3) 0.0127(4) Uani 1 1 d . . . . .
C12 C 0.67892(7) 0.4299(4) 0.5267(3) 0.0145(4) Uani 1 1 d . . . . .
H12 H 0.6662 0.5576 0.5832 0.017 Uiso 1 1 calc R U . . .
C13 C 0.72670(7) 0.4367(4) 0.5180(3) 0.0156(4) Uani 1 1 d . . . . .
H13 H 0.7465 0.5704 0.5685 0.019 Uiso 1 1 calc R U . . .
C14 C 0.74578(7) 0.2503(4) 0.4362(3) 0.0158(4) Uani 1 1 d . . . . .
H14 H 0.7784 0.2568 0.4310 0.019 Uiso 1 1 calc R U . . .
C15 C 0.71694(7) 0.0544(4) 0.3620(3) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.7298 -0.0728 0.3056 0.019 Uiso 1 1 calc R U . . .
C16 C 0.66907(7) 0.0444(4) 0.3703(3) 0.0143(4) Uani 1 1 d . . . . .
H16 H 0.6495 -0.0904 0.3209 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
C1 C2 1.383(3) . ?
C1 C9 1.420(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.420(3) . ?
C2 C21 1.500(3) . y
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C10 1.416(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(3) . ?
C5 C10 1.424(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(3) . ?
C21 O1 1.227(3) . ?
C21 N1 1.371(3) . y
N1 C11 1.416(2) . y
N1 H1N 0.85(3) . y
C11 C12 1.396(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 C1 C9 120.74(18) . . ?
C2 C1 H1 119.6 . . ?
C9 C1 H1 119.6 . . ?
C1 C2 C3 119.74(18) . . ?
C1 C2 C21 117.94(18) . . ?
C3 C2 C21 122.29(17) . . ?
C4 C3 C2 120.24(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 121.06(19) . . ?
C3 C4 H4 119.5 . . ?
C10 C4 H4 119.5 . . ?
C6 C5 C10 120.43(19) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.43(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.38(19) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.57(19) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C1 121.65(17) . . ?
C8 C9 C10 118.98(16) . . ?
C1 C9 C10 119.36(17) . . ?
C4 C10 C9 118.83(17) . . ?
C4 C10 C5 121.98(18) . . ?
C9 C10 C5 119.19(17) . . ?
O1 C21 N1 123.69(18) . . y
O1 C21 C2 122.66(17) . . y
N1 C21 C2 113.62(17) . . y
C21 N1 C11 126.35(17) . . y
C21 N1 H1N 116.2(18) . . ?
C11 N1 H1N 117.0(18) . . ?
C12 C11 C16 120.15(17) . . ?
C12 C11 N1 122.53(17) . . ?
C16 C11 N1 117.23(17) . . ?
C13 C12 C11 119.26(18) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.81(19) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.06(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 119.89(18) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 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
C9 C1 C2 C3 -1.6(3) . . . . ?
C9 C1 C2 C21 176.51(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C21 C2 C3 C4 -177.2(2) . . . . ?
C2 C3 C4 C10 0.9(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C1 178.48(19) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C2 C1 C9 C8 -178.0(2) . . . . ?
C2 C1 C9 C10 0.7(3) . . . . ?
C3 C4 C10 C9 -1.9(3) . . . . ?
C3 C4 C10 C5 178.6(2) . . . . ?
C8 C9 C10 C4 179.8(2) . . . . ?
C1 C9 C10 C4 1.1(3) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C1 C9 C10 C5 -179.4(2) . . . . ?
C6 C5 C10 C4 -179.3(2) . . . . ?
C6 C5 C10 C9 1.1(3) . . . . ?
C1 C2 C21 O1 29.1(3) . . . . y
C3 C2 C21 O1 -152.8(2) . . . . y
C1 C2 C21 N1 -149.0(2) . . . . y
C3 C2 C21 N1 29.0(3) . . . . y
O1 C21 N1 C11 0.1(4) . . . . y
C2 C21 N1 C11 178.20(19) . . . . y
C21 N1 C11 C12 33.8(3) . . . . y
C21 N1 C11 C16 -149.6(2) . . . . y
C16 C11 C12 C13 0.7(3) . . . . ?
N1 C11 C12 C13 177.21(19) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
N1 C11 C16 C15 -177.65(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.85(3) 2.51(3) 3.332(2) 165(2) 1_545
C1 H1 Cg1 0.95 2.97 3.700(2) 135 2_564
C4 H4 Cg1 0.95 2.81 3.482(2) 129 2_555
C8 H8 Cg2 0.95 2.82 3.433(2) 123 2_564
C12 H12 Cg3 0.95 2.96 3.652(2) 131 2_565
C15 H15 Cg3 0.95 2.90 3.570(2) 129 2_554

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_RA107_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 997580'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-(4-chlorophenyl)-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 Cl N O'
_chemical_formula_sum            'C17 H12 Cl N O'
_chemical_formula_weight         281.73


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.5994(11)
_cell_length_b                   7.4730(15)
_cell_length_c                   15.867(3)
_cell_angle_alpha                88.78(3)
_cell_angle_beta                 84.12(3)
_cell_angle_gamma                84.82(3)
_cell_volume                     657.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    3842
_cell_measurement_theta_min      5.187
_cell_measurement_theta_max      65.192

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8373
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12246
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.012
_diffrn_reflns_theta_max         33.287
_diffrn_reflns_theta_full        31.000
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4495
_reflns_number_gt                3668
_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-2013 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2103 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2013), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010)
;


_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)+(0.0539P)²+0.1777P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4495
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.5195(2) 0.31548(15) 0.35626(7) 0.0110(2) Uani 1 1 d . . . . .
H1 H 0.6522 0.3670 0.3760 0.013 Uiso 1 1 calc R U . . .
C2 C 0.3485(2) 0.24648(15) 0.41409(7) 0.0109(2) Uani 1 1 d . . . . .
C3 C 0.1501(2) 0.16666(16) 0.38488(7) 0.0123(2) Uani 1 1 d . . . . .
H3 H 0.0320 0.1200 0.4246 0.015 Uiso 1 1 calc R U . . .
C4 C 0.1296(2) 0.15722(15) 0.29915(7) 0.0119(2) Uani 1 1 d . . . . .
H4 H -0.0016 0.1020 0.2804 0.014 Uiso 1 1 calc R U . . .
C5 C 0.2830(2) 0.22145(16) 0.14945(7) 0.0137(2) Uani 1 1 d . . . . .
H5 H 0.1531 0.1670 0.1294 0.016 Uiso 1 1 calc R U . . .
C6 C 0.4531(2) 0.29318(17) 0.09245(7) 0.0155(2) Uani 1 1 d . . . . .
H6 H 0.4397 0.2873 0.0334 0.019 Uiso 1 1 calc R U . . .
C7 C 0.6480(2) 0.37563(17) 0.12139(7) 0.0147(2) Uani 1 1 d . . . . .
H7 H 0.7630 0.4256 0.0816 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6711(2) 0.38344(16) 0.20705(7) 0.0124(2) Uani 1 1 d . . . . .
H8 H 0.8027 0.4381 0.2258 0.015 Uiso 1 1 calc R U . . .
C9 C 0.4994(2) 0.31031(15) 0.26763(7) 0.0104(2) Uani 1 1 d . . . . .
C10 C 0.3015(2) 0.22877(15) 0.23838(7) 0.0107(2) Uani 1 1 d . . . . .
C21 C 0.3818(2) 0.25453(16) 0.50706(7) 0.0121(2) Uani 1 1 d . . . . .
O1 O 0.58275(16) 0.25810(13) 0.53220(5) 0.01728(19) Uani 1 1 d . . . . .
N1 N 0.17152(18) 0.25740(14) 0.55997(6) 0.01265(19) Uani 1 1 d . . . . .
H1N H 0.032(3) 0.272(2) 0.5361(10) 0.015 Uiso 1 1 d . U . . .
C11 C 0.1460(2) 0.24830(15) 0.64997(7) 0.0106(2) Uani 1 1 d . . . . .
C12 C 0.3266(2) 0.16781(15) 0.69722(7) 0.0118(2) Uani 1 1 d . . . . .
H12 H 0.4785 0.1238 0.6696 0.014 Uiso 1 1 calc R U . . .
C13 C 0.2810(2) 0.15307(15) 0.78534(7) 0.0119(2) Uani 1 1 d . . . . .
H13 H 0.4021 0.0990 0.8179 0.014 Uiso 1 1 calc R U . . .
C14 C 0.0578(2) 0.21771(15) 0.82532(7) 0.0120(2) Uani 1 1 d . . . . .
Cl14 Cl 0.00228(6) 0.19730(4) 0.93548(2) 0.01840(9) Uani 1 1 d . . . . .
C15 C -0.1223(2) 0.29942(16) 0.77915(7) 0.0124(2) Uani 1 1 d . . . . .
H15 H -0.2733 0.3443 0.8071 0.015 Uiso 1 1 calc R U . . .
C16 C -0.0775(2) 0.31425(15) 0.69136(7) 0.0118(2) Uani 1 1 d . . . . .
H16 H -0.1989 0.3694 0.6593 0.014 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
C1 C2 1.3831(16) . ?
C1 C9 1.4240(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.4291(16) . ?
C2 C21 1.5088(15) . y
C3 C4 1.3806(15) . ?
C3 H3 0.9500 . ?
C4 C10 1.4225(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3812(18) . ?
C5 C10 1.4279(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4203(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3814(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4248(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4331(16) . ?
C21 O1 1.2346(14) . y
C21 N1 1.3729(15) . y
N1 C11 1.4214(14) . y
N1 H1N 0.897(16) . y
C11 C16 1.4046(16) . ?
C11 C12 1.4048(16) . ?
C12 C13 1.3993(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3925(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3956(16) . ?
C14 Cl14 1.7496(12) . y
C15 C16 1.3937(15) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 C1 C9 120.91(10) . . ?
C2 C1 H1 119.5 . . ?
C9 C1 H1 119.5 . . ?
C1 C2 C3 119.85(10) . . ?
C1 C2 C21 118.27(10) . . ?
C3 C2 C21 121.87(10) . . ?
C4 C3 C2 120.19(11) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C10 121.10(11) . . ?
C3 C4 H4 119.4 . . ?
C10 C4 H4 119.4 . . ?
C6 C5 C10 120.32(11) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 120.56(10) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.31(11) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.64(11) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C1 C9 C8 121.83(10) . . ?
C1 C9 C10 119.18(10) . . ?
C8 C9 C10 118.99(10) . . ?
C4 C10 C5 122.06(10) . . ?
C4 C10 C9 118.76(10) . . ?
C5 C10 C9 119.18(11) . . ?
O1 C21 N1 123.71(10) . . y
O1 C21 C2 121.93(10) . . y
N1 C21 C2 114.36(10) . . y
C21 N1 C11 127.50(10) . . y
C21 N1 H1N 117.5(10) . . ?
C11 N1 H1N 114.9(10) . . ?
C16 C11 C12 119.96(10) . . ?
C16 C11 N1 116.99(10) . . ?
C12 C11 N1 122.94(10) . . ?
C13 C12 C11 119.41(10) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 119.91(10) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.19(10) . . ?
C13 C14 Cl14 119.49(9) . . y
C15 C14 Cl14 119.32(9) . . y
C16 C15 C14 119.03(11) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 120.48(10) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 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
C9 C1 C2 C3 0.80(16) . . . . ?
C9 C1 C2 C21 179.42(10) . . . . ?
C1 C2 C3 C4 0.43(16) . . . . ?
C21 C2 C3 C4 -178.14(10) . . . . ?
C2 C3 C4 C10 -1.08(17) . . . . ?
C10 C5 C6 C7 -0.21(18) . . . . ?
C5 C6 C7 C8 0.66(18) . . . . ?
C6 C7 C8 C9 -0.45(17) . . . . ?
C2 C1 C9 C8 178.87(11) . . . . ?
C2 C1 C9 C10 -1.36(16) . . . . ?
C7 C8 C9 C1 179.60(11) . . . . ?
C7 C8 C9 C10 -0.18(16) . . . . ?
C3 C4 C10 C5 -179.62(11) . . . . ?
C3 C4 C10 C9 0.50(16) . . . . ?
C6 C5 C10 C4 179.71(11) . . . . ?
C6 C5 C10 C9 -0.41(16) . . . . ?
C1 C9 C10 C4 0.70(16) . . . . ?
C8 C9 C10 C4 -179.52(10) . . . . ?
C1 C9 C10 C5 -179.17(10) . . . . ?
C8 C9 C10 C5 0.60(16) . . . . ?
C1 C2 C21 O1 -26.27(16) . . . . y
C3 C2 C21 O1 152.32(12) . . . . y
C1 C2 C21 N1 153.74(11) . . . . y
C3 C2 C21 N1 -27.67(15) . . . . y
O1 C21 N1 C11 -6.21(19) . . . . y
C2 C21 N1 C11 173.78(10) . . . . y
C21 N1 C11 C16 158.59(11) . . . . y
C21 N1 C11 C12 -25.31(18) . . . . y
C16 C11 C12 C13 0.46(17) . . . . ?
N1 C11 C12 C13 -175.52(10) . . . . ?
C11 C12 C13 C14 0.10(17) . . . . ?
C12 C13 C14 C15 -0.70(18) . . . . ?
C12 C13 C14 Cl14 179.62(9) . . . . y
C13 C14 C15 C16 0.72(18) . . . . ?
Cl14 C14 C15 C16 -179.60(9) . . . . y
C14 C15 C16 C11 -0.14(17) . . . . ?
C12 C11 C16 C15 -0.44(17) . . . . ?
N1 C11 C16 C15 175.78(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.897(16) 2.537(16) 3.3701(15) 154.7(13) 1_455
C16 H16 O1 0.95 2.65 3.3686(16) 133 1_455
C4 H4 Cg3 0.95 2.65 3.3860(14) 135 2_556
C8 H8 Cg3 0.95 2.65 3.4002(14) 137 2_666
C12 H12 Cg1 0.95 2.82 3.4580(14) 125 2_656
C13 H13 Cg1 0.95 3.01 3.6020(14) 121 2_656
C15 H15 Cg2 0.95 2.78 3.4603(14) 129 2_566
C16 H16 Cg1 0.95 2.97 3.5248(14) 119 2_566


_refine_diff_density_max         0.479
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_RA101_Compounds_5A_5B
_database_code_depnum_ccdc_archive 'CCDC 997581'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-(3-methoxyphenyl)-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   9.7762(5)
_cell_length_b                   11.4779(5)
_cell_length_c                   24.3526(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2732.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    5487
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.67

_exptl_crystal_description       'triangular plate'
_exptl_crystal_colour            colourles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8468
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51581
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.672
_diffrn_reflns_theta_max         33.437
_diffrn_reflns_theta_full        32.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9858
_reflns_number_gt                8343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.897
_reflns_Friedel_fraction_full    0.987

_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2013 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009), PublCIF (Westrip 2010)
;

_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)+(0.0685P)²+0.1371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9858
_refine_ls_number_parameters     387
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1A C 0.48237(17) 0.50281(14) 0.21559(6) 0.0127(3) Uani 1 1 d . . . . .
H1A H 0.4176 0.5610 0.2059 0.015 Uiso 1 1 calc R U . . .
C2A C 0.57929(17) 0.46817(13) 0.17791(6) 0.0124(3) Uani 1 1 d . . . . .
C3A C 0.67883(17) 0.38407(14) 0.19288(6) 0.0139(3) Uani 1 1 d . . . . .
H3A H 0.7486 0.3634 0.1675 0.017 Uiso 1 1 calc R U . . .
C4A C 0.67540(17) 0.33226(14) 0.24358(6) 0.0149(3) Uani 1 1 d . . . . .
H4A H 0.7415 0.2747 0.2527 0.018 Uiso 1 1 calc R U . . .
C5A C 0.56421(19) 0.30990(14) 0.33497(6) 0.0161(3) Uani 1 1 d . . . . .
H5A H 0.6276 0.2508 0.3448 0.019 Uiso 1 1 calc R U . . .
C6A C 0.46432(19) 0.34218(14) 0.37145(6) 0.0175(3) Uani 1 1 d . . . . .
H6A H 0.4578 0.3041 0.4060 0.021 Uiso 1 1 calc R U . . .
C7A C 0.37105(18) 0.43177(14) 0.35790(6) 0.0165(3) Uani 1 1 d . . . . .
H7A H 0.3031 0.4544 0.3836 0.020 Uiso 1 1 calc R U . . .
C8A C 0.37803(17) 0.48619(14) 0.30789(6) 0.0145(3) Uani 1 1 d . . . . .
H8A H 0.3154 0.5468 0.2993 0.017 Uiso 1 1 calc R U . . .
C9A C 0.47843(17) 0.45241(13) 0.26878(6) 0.0123(3) Uani 1 1 d . . . . .
C10A C 0.57386(17) 0.36382(13) 0.28271(6) 0.0132(3) Uani 1 1 d . . . . .
C21A C 0.58536(17) 0.51724(13) 0.12099(6) 0.0126(3) Uani 1 1 d . . . . .
O1A O 0.69618(12) 0.52899(11) 0.09723(5) 0.0180(3) Uani 1 1 d . . . . .
N1A N 0.46342(15) 0.54409(12) 0.09786(5) 0.0125(2) Uani 1 1 d D . . . .
H1NA H 0.3918(19) 0.5347(19) 0.1173(7) 0.015 Uiso 1 1 d D U . . .
C11A C 0.44320(17) 0.59231(13) 0.04471(6) 0.0122(3) Uani 1 1 d . . . . .
C12A C 0.52740(17) 0.56357(13) 0.00085(6) 0.0133(3) Uani 1 1 d . . . . .
H12A H 0.6011 0.5106 0.0058 0.016 Uiso 1 1 calc R U . . .
C13A C 0.50298(17) 0.61316(14) -0.05078(6) 0.0134(3) Uani 1 1 d . . . . .
O13A O 0.59216(13) 0.57961(11) -0.09106(4) 0.0186(3) Uani 1 1 d . . . . .
C131 C 0.5711(2) 0.62537(16) -0.14506(6) 0.0201(3) Uani 1 1 d . . . . .
H13A H 0.4775 0.6084 -0.1570 0.030 Uiso 1 1 calc R U . . .
H13B H 0.6360 0.5892 -0.1705 0.030 Uiso 1 1 calc R U . . .
H13C H 0.5855 0.7099 -0.1447 0.030 Uiso 1 1 calc R U . . .
C14A C 0.39470(17) 0.68986(14) -0.05852(6) 0.0151(3) Uani 1 1 d . . . . .
H14A H 0.3794 0.7245 -0.0934 0.018 Uiso 1 1 calc R U . . .
C15A C 0.30895(18) 0.71525(14) -0.01443(6) 0.0163(3) Uani 1 1 d . . . . .
H15A H 0.2336 0.7663 -0.0197 0.020 Uiso 1 1 calc R U . . .
C16A C 0.33188(17) 0.66713(14) 0.03700(6) 0.0147(3) Uani 1 1 d . . . . .
H16A H 0.2725 0.6848 0.0667 0.018 Uiso 1 1 calc R U . . .
C1B C 0.97891(17) 0.48881(13) 0.03689(6) 0.0126(3) Uani 1 1 d . . . . .
H1B H 0.9127 0.5471 0.0447 0.015 Uiso 1 1 calc R U . . .
C2B C 1.07813(17) 0.46358(13) 0.07501(6) 0.0120(3) Uani 1 1 d . . . . .
C3B C 1.17981(17) 0.37865(14) 0.06310(6) 0.0146(3) Uani 1 1 d . . . . .
H3B H 1.2512 0.3645 0.0887 0.017 Uiso 1 1 calc R U . . .
C4B C 1.17533(18) 0.31699(14) 0.01485(6) 0.0152(3) Uani 1 1 d . . . . .
H4B H 1.2424 0.2590 0.0078 0.018 Uiso 1 1 calc R U . . .
C5B C 1.06168(18) 0.27544(14) -0.07457(7) 0.0172(3) Uani 1 1 d . . . . .
H5B H 1.1246 0.2143 -0.0819 0.021 Uiso 1 1 calc R U . . .
C6B C 0.96199(19) 0.30163(15) -0.11228(7) 0.0179(3) Uani 1 1 d . . . . .
H6B H 0.9565 0.2584 -0.1455 0.022 Uiso 1 1 calc R U . . .
C7B C 0.86756(19) 0.39205(15) -0.10223(6) 0.0171(3) Uani 1 1 d . . . . .
H7B H 0.7996 0.4100 -0.1288 0.021 Uiso 1 1 calc R U . . .
C8B C 0.87362(17) 0.45422(14) -0.05411(6) 0.0147(3) Uani 1 1 d . . . . .
H8B H 0.8097 0.5150 -0.0476 0.018 Uiso 1 1 calc R U . . .
C9B C 0.97440(17) 0.42853(13) -0.01414(6) 0.0125(3) Uani 1 1 d . . . . .
C10B C 1.07162(18) 0.33893(13) -0.02461(6) 0.0136(3) Uani 1 1 d . . . . .
C21B C 1.08541(17) 0.52229(13) 0.12984(6) 0.0129(3) Uani 1 1 d . . . . .
O1B O 1.19649(12) 0.53917(12) 0.15275(5) 0.0179(3) Uani 1 1 d . . . . .
N1B N 0.96372(15) 0.55366(12) 0.15231(5) 0.0131(3) Uani 1 1 d D . . . .
H1NB H 0.8902(18) 0.5420(19) 0.1329(7) 0.016 Uiso 1 1 d D U . . .
C11B C 0.94421(17) 0.60998(13) 0.20376(6) 0.0127(3) Uani 1 1 d . . . . .
C12B C 1.03270(17) 0.59251(14) 0.24766(6) 0.0144(3) Uani 1 1 d . . . . .
H12B H 1.1094 0.5423 0.2439 0.017 Uiso 1 1 calc R U . . .
C13B C 1.00769(17) 0.64956(14) 0.29737(6) 0.0146(3) Uani 1 1 d . . . . .
O13B O 1.10001(13) 0.62620(12) 0.33826(5) 0.0204(3) Uani 1 1 d . . . . .
C132 C 1.07142(19) 0.67022(16) 0.39192(6) 0.0202(3) Uani 1 1 d . . . . .
H13D H 1.0764 0.7555 0.3915 0.030 Uiso 1 1 calc R U . . .
H13E H 1.1387 0.6395 0.4180 0.030 Uiso 1 1 calc R U . . .
H13F H 0.9795 0.6459 0.4031 0.030 Uiso 1 1 calc R U . . .
C14B C 0.89590(18) 0.72357(14) 0.30344(7) 0.0173(3) Uani 1 1 d . . . . .
H14B H 0.8805 0.7636 0.3370 0.021 Uiso 1 1 calc R U . . .
C15B C 0.80696(19) 0.73777(15) 0.25912(7) 0.0186(3) Uani 1 1 d . . . . .
H15B H 0.7292 0.7867 0.2630 0.022 Uiso 1 1 calc R U . . .
C16B C 0.82986(17) 0.68181(15) 0.20957(6) 0.0158(3) Uani 1 1 d . . . . .
H16B H 0.7683 0.6922 0.1798 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
C1A C2A 1.378(2) . ?
C1A C9A 1.419(2) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.418(2) . ?
C2A C21A 1.497(2) . y
C3A C4A 1.371(2) . ?
C3A H3A 0.9500 . ?
C4A C10A 1.423(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.371(2) . ?
C5A C10A 1.418(2) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.413(2) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.370(2) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.422(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.421(2) . ?
C21A O1A 1.2356(19) . y
C21A N1A 1.354(2) . y
N1A C11A 1.4214(18) . y
N1A H1NA 0.852(17) . y
C11A C12A 1.388(2) . ?
C11A C16A 1.399(2) . ?
C12A C13A 1.401(2) . ?
C12A H12A 0.9500 . ?
C13A O13A 1.3677(19) . y
C13A C14A 1.390(2) . ?
O13A C131 1.4310(18) . y
C131 H13A 0.9800 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C14A C15A 1.393(2) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.387(2) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C1B C2B 1.374(2) . ?
C1B C9B 1.423(2) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.422(2) . ?
C2B C21B 1.497(2) . y
C3B C4B 1.372(2) . ?
C3B H3B 0.9500 . ?
C4B C10B 1.420(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.372(2) . ?
C5B C10B 1.421(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.410(2) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.373(2) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.416(2) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.423(2) . ?
C21B O1B 1.2362(19) . y
C21B N1B 1.358(2) . y
N1B C11B 1.4229(18) . y
N1B H1NB 0.871(17) . y
C11B C12B 1.390(2) . ?
C11B C16B 1.396(2) . ?
C12B C13B 1.398(2) . ?
C12B H12B 0.9500 . ?
C13B O13B 1.3703(19) . y
C13B C14B 1.392(2) . ?
O13B C132 1.4287(18) . y
C132 H13D 0.9800 . ?
C132 H13E 0.9800 . ?
C132 H13F 0.9800 . ?
C14B C15B 1.396(2) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.385(2) . ?
C15B H15B 0.9500 . ?
C16B H16B 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
C2A C1A C9A 120.59(14) . . ?
C2A C1A H1A 119.7 . . ?
C9A C1A H1A 119.7 . . ?
C1A C2A C3A 119.81(13) . . ?
C1A C2A C21A 122.36(14) . . y
C3A C2A C21A 117.82(14) . . y
C4A C3A C2A 120.65(15) . . ?
C4A C3A H3A 119.7 . . ?
C2A C3A H3A 119.7 . . ?
C3A C4A C10A 120.65(15) . . ?
C3A C4A H4A 119.7 . . ?
C10A C4A H4A 119.7 . . ?
C6A C5A C10A 120.72(15) . . ?
C6A C5A H5A 119.6 . . ?
C10A C5A H5A 119.6 . . ?
C5A C6A C7A 120.32(14) . . ?
C5A C6A H6A 119.8 . . ?
C7A C6A H6A 119.8 . . ?
C8A C7A C6A 120.45(15) . . ?
C8A C7A H7A 119.8 . . ?
C6A C7A H7A 119.8 . . ?
C7A C8A C9A 120.36(15) . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A H8A 119.8 . . ?
C1A C9A C10A 119.46(14) . . ?
C1A C9A C8A 121.27(14) . . ?
C10A C9A C8A 119.24(13) . . ?
C5A C10A C9A 118.87(14) . . ?
C5A C10A C4A 122.43(15) . . ?
C9A C10A C4A 118.70(13) . . ?
O1A C21A N1A 123.52(13) . . y
O1A C21A C2A 120.62(14) . . y
N1A C21A C2A 115.84(14) . . y
C21A N1A C11A 126.15(14) . . y
C21A N1A H1NA 117.6(13) . . ?
C11A N1A H1NA 116.2(13) . . ?
C12A C11A C16A 120.26(13) . . ?
C12A C11A N1A 121.71(14) . . ?
C16A C11A N1A 118.00(13) . . ?
C11A C12A C13A 119.54(14) . . ?
C11A C12A H12A 120.2 . . ?
C13A C12A H12A 120.2 . . ?
O13A C13A C14A 124.52(13) . . y
O13A C13A C12A 114.88(14) . . y
C14A C13A C12A 120.60(14) . . ?
C13A O13A C131 117.66(13) . . y
O13A C131 H13A 109.5 . . ?
O13A C131 H13B 109.5 . . ?
H13A C131 H13B 109.5 . . ?
O13A C131 H13C 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C13A C14A C15A 119.11(14) . . ?
C13A C14A H14A 120.4 . . ?
C15A C14A H14A 120.4 . . ?
C16A C15A C14A 121.02(15) . . ?
C16A C15A H15A 119.5 . . ?
C14A C15A H15A 119.5 . . ?
C15A C16A C11A 119.43(14) . . ?
C15A C16A H16A 120.3 . . ?
C11A C16A H16A 120.3 . . ?
C2B C1B C9B 120.64(14) . . ?
C2B C1B H1B 119.7 . . ?
C9B C1B H1B 119.7 . . ?
C1B C2B C3B 120.02(14) . . ?
C1B C2B C21B 122.78(14) . . y
C3B C2B C21B 117.20(13) . . y
C4B C3B C2B 120.39(15) . . ?
C4B C3B H3B 119.8 . . ?
C2B C3B H3B 119.8 . . ?
C3B C4B C10B 120.73(15) . . ?
C3B C4B H4B 119.6 . . ?
C10B C4B H4B 119.6 . . ?
C6B C5B C10B 120.60(15) . . ?
C6B C5B H5B 119.7 . . ?
C10B C5B H5B 119.7 . . ?
C5B C6B C7B 120.65(15) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C8B C7B C6B 120.15(16) . . ?
C8B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
C7B C8B C9B 120.55(15) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B H8B 119.7 . . ?
C8B C9B C1B 121.37(14) . . ?
C8B C9B C10B 119.46(14) . . ?
C1B C9B C10B 119.15(14) . . ?
C4B C10B C5B 122.50(15) . . ?
C4B C10B C9B 118.93(14) . . ?
C5B C10B C9B 118.56(15) . . ?
O1B C21B N1B 123.10(14) . . y
O1B C21B C2B 120.99(14) . . y
N1B C21B C2B 115.91(14) . . y
C21B N1B C11B 126.35(14) . . y
C21B N1B H1NB 117.6(13) . . ?
C11B N1B H1NB 116.0(13) . . ?
C12B C11B C16B 120.38(14) . . ?
C12B C11B N1B 121.90(14) . . ?
C16B C11B N1B 117.70(14) . . ?
C11B C12B C13B 119.32(14) . . ?
C11B C12B H12B 120.3 . . ?
C13B C12B H12B 120.3 . . ?
O13B C13B C14B 124.01(14) . . y
O13B C13B C12B 114.99(14) . . y
C14B C13B C12B 121.00(15) . . ?
C13B O13B C132 117.81(13) . . y
O13B C132 H13D 109.5 . . ?
O13B C132 H13E 109.5 . . ?
H13D C132 H13E 109.5 . . ?
O13B C132 H13F 109.5 . . ?
H13D C132 H13F 109.5 . . ?
H13E C132 H13F 109.5 . . ?
C13B C14B C15B 118.58(15) . . ?
C13B C14B H14B 120.7 . . ?
C15B C14B H14B 120.7 . . ?
C16B C15B C14B 121.25(15) . . ?
C16B C15B H15B 119.4 . . ?
C14B C15B H15B 119.4 . . ?
C15B C16B C11B 119.44(15) . . ?
C15B C16B H16B 120.3 . . ?
C11B C16B H16B 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
C9A C1A C2A C3A -2.0(2) . . . . ?
C9A C1A C2A C21A 178.72(14) . . . . ?
C1A C2A C3A C4A 3.4(2) . . . . ?
C21A C2A C3A C4A -177.27(14) . . . . ?
C2A C3A C4A C10A -1.5(2) . . . . ?
C10A C5A C6A C7A -1.4(2) . . . . ?
C5A C6A C7A C8A 1.0(3) . . . . ?
C6A C7A C8A C9A 0.6(2) . . . . ?
C2A C1A C9A C10A -1.2(2) . . . . ?
C2A C1A C9A C8A -179.22(15) . . . . ?
C7A C8A C9A C1A 176.26(15) . . . . ?
C7A C8A C9A C10A -1.7(2) . . . . ?
C6A C5A C10A C9A 0.2(2) . . . . ?
C6A C5A C10A C4A -179.56(16) . . . . ?
C1A C9A C10A C5A -176.71(14) . . . . ?
C8A C9A C10A C5A 1.3(2) . . . . ?
C1A C9A C10A C4A 3.1(2) . . . . ?
C8A C9A C10A C4A -178.89(14) . . . . ?
C3A C4A C10A C5A 178.07(15) . . . . ?
C3A C4A C10A C9A -1.7(2) . . . . ?
C1A C2A C21A O1A 147.17(16) . . . . y
C3A C2A C21A O1A -32.1(2) . . . . y
C1A C2A C21A N1A -34.4(2) . . . . y
C3A C2A C21A N1A 146.33(15) . . . . y
O1A C21A N1A C11A -2.1(2) . . . . y
C2A C21A N1A C11A 179.49(14) . . . . y
C21A N1A C11A C12A 34.5(2) . . . . y
C21A N1A C11A C16A -147.83(16) . . . . y
C16A C11A C12A C13A 2.2(2) . . . . ?
N1A C11A C12A C13A 179.80(14) . . . . ?
C11A C12A C13A O13A 179.66(14) . . . . ?
C11A C12A C13A C14A -0.6(2) . . . . ?
C14A C13A O13A C131 -1.0(2) . . . . y
C12A C13A O13A C131 178.77(14) . . . . y
O13A C13A C14A C15A 178.56(15) . . . . y
C12A C13A C14A C15A -1.2(2) . . . . ?
C13A C14A C15A C16A 1.3(3) . . . . ?
C14A C15A C16A C11A 0.3(2) . . . . ?
C12A C11A C16A C15A -2.0(2) . . . . ?
N1A C11A C16A C15A -179.73(15) . . . . ?
C9B C1B C2B C3B 1.7(2) . . . . ?
C9B C1B C2B C21B -178.45(14) . . . . ?
C1B C2B C3B C4B -3.5(2) . . . . ?
C21B C2B C3B C4B 176.58(14) . . . . ?
C2B C3B C4B C10B 1.7(2) . . . . ?
C10B C5B C6B C7B 0.0(3) . . . . ?
C5B C6B C7B C8B -0.7(3) . . . . ?
C6B C7B C8B C9B 0.0(2) . . . . ?
C7B C8B C9B C1B -177.45(15) . . . . ?
C7B C8B C9B C10B 1.2(2) . . . . ?
C2B C1B C9B C8B -179.39(15) . . . . ?
C2B C1B C9B C10B 1.9(2) . . . . ?
C3B C4B C10B C5B -178.69(15) . . . . ?
C3B C4B C10B C9B 1.9(2) . . . . ?
C6B C5B C10B C4B -178.22(16) . . . . ?
C6B C5B C10B C9B 1.2(2) . . . . ?
C8B C9B C10B C4B 177.62(15) . . . . ?
C1B C9B C10B C4B -3.7(2) . . . . ?
C8B C9B C10B C5B -1.8(2) . . . . ?
C1B C9B C10B C5B 176.87(14) . . . . ?
C1B C2B C21B O1B -148.36(16) . . . . y
C3B C2B C21B O1B 31.5(2) . . . . y
C1B C2B C21B N1B 32.4(2) . . . . y
C3B C2B C21B N1B -147.73(15) . . . . y
O1B C21B N1B C11B 0.6(2) . . . . y
C2B C21B N1B C11B 179.83(14) . . . . y
C21B N1B C11B C12B -30.9(2) . . . . y
C21B N1B C11B C16B 150.93(16) . . . . y
C16B C11B C12B C13B -1.4(2) . . . . ?
N1B C11B C12B C13B -179.50(14) . . . . ?
C11B C12B C13B O13B 179.59(14) . . . . y
C11B C12B C13B C14B -0.1(2) . . . . ?
C14B C13B O13B C132 7.2(2) . . . . y
C12B C13B O13B C132 -172.55(15) . . . . y
O13B C13B C14B C15B -178.24(16) . . . . y
C12B C13B C14B C15B 1.5(2) . . . . ?
C13B C14B C15B C16B -1.3(3) . . . . ?
C14B C15B C16B C11B -0.1(3) . . . . ?
C12B C11B C16B C15B 1.5(2) . . . . ?
N1B C11B C16B C15B 179.71(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1B H1NB O1A 0.871(17) 2.091(17) 2.9530(18) 170.1(19) .
C12A H12A O1A 0.95 2.42 2.8963(19) 111 .
C12B H12B O1B 0.95 2.38 2.8775(19) 112 .
C1B H1B O1A 0.95 2.48 3.164(2) 129 .
C8B H8B O13A 0.95 2.49 3.233(2) 135.2 .
N1A H1NA O1B 0.852(17) 2.096(17) 2.9326(18) 167.0(19) 1_455
C1A H1A O1B 0.95 2.53 3.214(2) 129 1_455
C8A H8A O13B 0.95 2.48 3.243(2) 137 1_455
C132 H13F O13A 0.98 2.69 3.309(2) 122 2_665

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_RA99_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 997578'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-cyclohexyl-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.1820(9)
_cell_length_b                   6.5439(11)
_cell_length_c                   19.416(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.448(9)
_cell_angle_gamma                90
_cell_volume                     657.81(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    4169
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      32.44


_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8339
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10572
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.286
_diffrn_reflns_theta_max         33.395
_diffrn_reflns_theta_full        30.500
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             4420
_reflns_number_gt                3873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.824
_reflns_Friedel_fraction_full    0.947

_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-2013 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-2013 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009), PublCIF (Westrip 2010)
;



_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)+(0.1095P)²+0.0256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4420
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
C1 C 1.0564(4) 1.1071(3) 0.20211(11) 0.0134(4) Uani 1 1 d . . . . .
H1 H 1.2062 1.0938 0.2318 0.016 Uiso 1 1 calc R U . . .
C2 C 0.8978(4) 1.2742(3) 0.20886(11) 0.0130(4) Uani 1 1 d . . . . .
C3 C 0.6731(4) 1.2936(3) 0.16485(11) 0.0150(4) Uani 1 1 d . . . . .
H3 H 0.5610 1.4069 0.1700 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6172(4) 1.1507(4) 0.11520(11) 0.0151(4) Uani 1 1 d . . . . .
H4 H 0.4679 1.1674 0.0856 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7254(4) 0.8286(3) 0.05527(11) 0.0154(4) Uani 1 1 d . . . . .
H5 H 0.5777 0.8433 0.0250 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8855(4) 0.6632(4) 0.04840(12) 0.0172(4) Uani 1 1 d . . . . .
H6 H 0.8486 0.5645 0.0134 0.021 Uiso 1 1 calc R U . . .
C7 C 1.1055(4) 0.6398(4) 0.09347(12) 0.0177(4) Uani 1 1 d . . . . .
H7 H 1.2159 0.5252 0.0886 0.021 Uiso 1 1 calc R U . . .
C8 C 1.1608(4) 0.7810(3) 0.14404(12) 0.0154(4) Uani 1 1 d . . . . .
H8 H 1.3080 0.7623 0.1742 0.018 Uiso 1 1 calc R U . . .
C9 C 1.0008(4) 0.9551(3) 0.15196(10) 0.0132(4) Uani 1 1 d . . . . .
C10 C 0.7779(4) 0.9775(3) 0.10696(10) 0.0133(4) Uani 1 1 d . . . . .
C21 C 0.9706(4) 1.4337(3) 0.26164(10) 0.0128(4) Uani 1 1 d . . . . .
O1 O 1.1980(3) 1.4602(3) 0.28129(8) 0.0170(3) Uani 1 1 d . . . . .
N1 N 0.7738(3) 1.5456(3) 0.28438(9) 0.0137(3) Uani 1 1 d . . . . .
H1N H 0.608(5) 1.504(5) 0.2733(15) 0.016 Uiso 1 1 d . U . . .
C11 C 0.8136(4) 1.7100(3) 0.33455(11) 0.0132(4) Uani 1 1 d . . . . .
H11 H 0.9889 1.7696 0.3285 0.016 Uiso 1 1 calc R U . . .
C12 C 0.8025(5) 1.6310(4) 0.40831(12) 0.0191(4) Uani 1 1 d . . . . .
H12A H 0.9400 1.5279 0.4168 0.023 Uiso 1 1 calc R U . . .
H12B H 0.6340 1.5637 0.4144 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8376(4) 1.8046(4) 0.46039(12) 0.0201(4) Uani 1 1 d . . . . .
H13A H 1.0142 1.8612 0.4580 0.024 Uiso 1 1 calc R U . . .
H13B H 0.8180 1.7504 0.5075 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6403(4) 1.9747(4) 0.44633(12) 0.0197(4) Uani 1 1 d . . . . .
H14A H 0.4650 1.9224 0.4546 0.024 Uiso 1 1 calc R U . . .
H14B H 0.6763 2.0891 0.4787 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6488(4) 2.0528(4) 0.37229(12) 0.0193(4) Uani 1 1 d . . . . .
H15A H 0.5105 2.1553 0.3639 0.023 Uiso 1 1 calc R U . . .
H15B H 0.8167 2.1206 0.3657 0.023 Uiso 1 1 calc R U . . .
C16 C 0.6132(4) 1.8783(3) 0.32075(11) 0.0157(4) Uani 1 1 d . . . . .
H16A H 0.6297 1.9317 0.2734 0.019 Uiso 1 1 calc R U . . .
H16B H 0.4377 1.8203 0.3239 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
C1 C2 1.377(3) . ?
C1 C9 1.413(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.420(3) . ?
C2 C21 1.500(3) . y
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 C10 1.419(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(3) . ?
C5 C10 1.417(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(3) . ?
C21 O1 1.235(2) . y
C21 N1 1.345(3) . y
N1 C11 1.460(3) . y
N1 H1N 0.92(3) . y
C11 C12 1.526(3) . ?
C11 C16 1.529(3) . ?
C11 H11 1.0000 . ?
C12 C13 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.528(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C2 C1 C9 121.28(18) . . ?
C2 C1 H1 119.4 . . ?
C9 C1 H1 119.4 . . ?
C1 C2 C3 119.41(19) . . ?
C1 C2 C21 118.93(18) . . ?
C3 C2 C21 121.65(18) . . ?
C4 C3 C2 120.50(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C10 121.23(18) . . ?
C3 C4 H4 119.4 . . ?
C10 C4 H4 119.4 . . ?
C6 C5 C10 120.82(19) . . ?
C6 C5 H5 119.6 . . ?
C10 C5 H5 119.6 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.89(19) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C1 C9 C8 122.42(18) . . ?
C1 C9 C10 119.07(18) . . ?
C8 C9 C10 118.51(18) . . ?
C5 C10 C4 122.22(18) . . ?
C5 C10 C9 119.28(18) . . ?
C4 C10 C9 118.49(18) . . ?
O1 C21 N1 123.3(2) . . y
O1 C21 C2 121.17(18) . . y
N1 C21 C2 115.55(17) . . y
C21 N1 C11 122.20(17) . . y
C21 N1 H1N 118(2) . . ?
C11 N1 H1N 119(2) . . ?
N1 C11 C12 111.51(18) . . ?
N1 C11 C16 109.77(16) . . ?
C12 C11 C16 110.86(16) . . ?
N1 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C16 C11 H11 108.2 . . ?
C11 C12 C13 111.18(19) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 111.34(19) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 111.46(18) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 111.06(19) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C11 111.24(17) . . ?
C15 C16 H16A 109.4 . . ?
C11 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C11 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?

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
C9 C1 C2 C3 0.4(3) . . . . ?
C9 C1 C2 C21 -178.26(17) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C21 C2 C3 C4 177.14(18) . . . . ?
C2 C3 C4 C10 1.2(3) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C2 C1 C9 C8 -179.82(19) . . . . ?
C2 C1 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C1 -177.9(2) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C6 C5 C10 C4 179.67(19) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C3 C4 C10 C5 -179.20(19) . . . . ?
C3 C4 C10 C9 0.1(3) . . . . ?
C1 C9 C10 C5 178.16(18) . . . . ?
C8 C9 C10 C5 -1.1(3) . . . . ?
C1 C9 C10 C4 -1.2(3) . . . . ?
C8 C9 C10 C4 179.56(19) . . . . ?
C1 C2 C21 O1 25.7(3) . . . . y
C3 C2 C21 O1 -152.9(2) . . . . y
C1 C2 C21 N1 -155.51(19) . . . . y
C3 C2 C21 N1 25.9(3) . . . . y
O1 C21 N1 C11 0.2(3) . . . . y
C2 C21 N1 C11 -178.55(18) . . . . y
C21 N1 C11 C12 -89.1(2) . . . . y
C21 N1 C11 C16 147.66(19) . . . . y
N1 C11 C12 C13 -178.59(17) . . . . ?
C16 C11 C12 C13 -56.0(2) . . . . ?
C11 C12 C13 C14 55.3(2) . . . . ?
C12 C13 C14 C15 -54.8(2) . . . . ?
C13 C14 C15 C16 55.0(2) . . . . ?
C14 C15 C16 C11 -55.8(2) . . . . ?
N1 C11 C16 C15 179.96(16) . . . . ?
C12 C11 C16 C15 56.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.92(3) 2.15(3) 3.034(2) 160(3) 1_455
C16 H16A Cg1 0.99 2.82 3.774(2) 161 1_565

_iucr_geom_hbonds_special_details 
;
Cg1 is the centroid of the C1...C4,C9,C10 ring.
;

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_RA100_Compound_6
_database_code_depnum_ccdc_archive 'CCDC 997582'
_audit_update_record             
;
2014-04-15 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-(4-methoxyphenyl)-2-naphthamide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.5162(6)
_cell_length_b                   7.4987(7)
_cell_length_c                   16.1006(17)
_cell_angle_alpha                86.535(3)
_cell_angle_beta                 87.169(4)
_cell_angle_gamma                86.154(4)
_cell_volume                     662.59(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    89(2)
_cell_measurement_reflns_used    4031
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      33.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      89(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_number            12388
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.268
_diffrn_reflns_theta_max         33.422
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4594
_reflns_number_gt                3658
_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       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010)
;


_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)+(0.0933P)²+0.0583P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.072
_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
C1 C 0.99517(17) 0.33004(12) -0.14041(6) 0.01122(18) Uani 1 1 d . . . . .
H1 H 1.1331 0.3838 -0.1224 0.013 Uiso 1 1 calc R U . . .
C2 C 0.83365(17) 0.25680(13) -0.08227(6) 0.01117(18) Uani 1 1 d . . . . .
C3 C 0.62814(18) 0.17481(13) -0.10901(6) 0.01270(19) Uani 1 1 d . . . . .
H3 H 0.5160 0.1248 -0.0689 0.015 Uiso 1 1 calc R U . . .
C4 C 0.59047(17) 0.16737(13) -0.19239(6) 0.01208(19) Uani 1 1 d . . . . .
H4 H 0.4534 0.1110 -0.2094 0.015 Uiso 1 1 calc R U . . .
C5 C 0.71976(18) 0.23534(13) -0.33995(6) 0.01345(19) Uani 1 1 d . . . . .
H5 H 0.5846 0.1785 -0.3581 0.016 Uiso 1 1 calc R U . . .
C6 C 0.8805(2) 0.30957(14) -0.39752(6) 0.0157(2) Uani 1 1 d . . . . .
H6 H 0.8573 0.3027 -0.4553 0.019 Uiso 1 1 calc R U . . .
C7 C 1.08158(19) 0.39666(14) -0.37124(6) 0.0153(2) Uani 1 1 d . . . . .
H7 H 1.1904 0.4500 -0.4115 0.018 Uiso 1 1 calc R U . . .
C8 C 1.11989(18) 0.40433(13) -0.28775(6) 0.01326(19) Uani 1 1 d . . . . .
H8 H 1.2556 0.4623 -0.2708 0.016 Uiso 1 1 calc R U . . .
C9 C 0.95856(17) 0.32640(12) -0.22680(6) 0.01058(18) Uani 1 1 d . . . . .
C10 C 0.75338(17) 0.24264(12) -0.25316(5) 0.01084(18) Uani 1 1 d . . . . .
C21 C 0.88392(18) 0.26113(13) 0.00822(6) 0.01228(19) Uani 1 1 d . . . . .
O1 O 1.09226(13) 0.26469(11) 0.03225(4) 0.01734(17) Uani 1 1 d . . . . .
N1 N 0.68219(15) 0.26007(12) 0.06041(5) 0.01280(17) Uani 1 1 d D . . . .
H1N H 0.539(2) 0.275(2) 0.0368(9) 0.030(4) Uiso 1 1 d D . . . .
C11 C 0.67198(17) 0.24217(12) 0.14872(5) 0.01042(18) Uani 1 1 d . . . . .
C12 C 0.85923(18) 0.15541(13) 0.19448(6) 0.01185(18) Uani 1 1 d . . . . .
H12 H 1.0076 0.1152 0.1671 0.014 Uiso 1 1 calc R U . . .
C13 C 0.82621(17) 0.12870(13) 0.28029(6) 0.01201(18) Uani 1 1 d . . . . .
H13 H 0.9526 0.0690 0.3114 0.014 Uiso 1 1 calc R U . . .
C14 C 0.61059(18) 0.18809(12) 0.32136(5) 0.01130(18) Uani 1 1 d . . . . .
O14 O 0.59730(14) 0.15247(10) 0.40633(4) 0.01578(17) Uani 1 1 d . . . . .
C141 C 0.3743(2) 0.20544(15) 0.44894(6) 0.0198(2) Uani 1 1 d . . . . .
H14A H 0.3453 0.3358 0.4422 0.030 Uiso 1 1 calc R U . . .
H14B H 0.3834 0.1692 0.5083 0.030 Uiso 1 1 calc R U . . .
H14C H 0.2407 0.1478 0.4257 0.030 Uiso 1 1 calc R U . . .
C15 C 0.42567(18) 0.27657(13) 0.27618(6) 0.01188(18) Uani 1 1 d . . . . .
H15 H 0.2787 0.3188 0.3038 0.014 Uiso 1 1 calc R U . . .
C16 C 0.45803(17) 0.30284(13) 0.18992(6) 0.01156(18) Uani 1 1 d . . . . .
H16 H 0.3318 0.3631 0.1589 0.014 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
C1 C2 1.3758(13) . ?
C1 C9 1.4175(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.4221(13) . ?
C2 C21 1.4991(12) . ?
C3 C4 1.3735(12) . ?
C3 H3 0.9500 . ?
C4 C10 1.4135(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3705(14) . ?
C5 C10 1.4234(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.4185(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.3762(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.4180(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.4250(13) . ?
C21 O1 1.2331(12) . ?
C21 N1 1.3610(12) . ?
N1 C11 1.4187(11) . ?
N1 H1N 0.891(13) . ?
C11 C16 1.3881(13) . ?
C11 C12 1.4001(13) . ?
C12 C13 1.3888(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3918(13) . ?
C13 H13 0.9500 . ?
C14 O14 1.3773(11) . ?
C14 C15 1.3907(14) . ?
O14 C141 1.4231(13) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C15 C16 1.3953(12) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 C1 C9 120.90(8) . . ?
C2 C1 H1 119.5 . . ?
C9 C1 H1 119.5 . . ?
C1 C2 C3 119.69(8) . . ?
C1 C2 C21 118.66(8) . . ?
C3 C2 C21 121.63(8) . . ?
C4 C3 C2 120.51(9) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C10 120.73(8) . . ?
C3 C4 H4 119.6 . . ?
C10 C4 H4 119.6 . . ?
C6 C5 C10 120.61(9) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 120.29(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.36(9) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.58(9) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C1 C9 C8 121.86(8) . . ?
C1 C9 C10 119.09(8) . . ?
C8 C9 C10 119.05(8) . . ?
C4 C10 C5 121.86(8) . . ?
C4 C10 C9 119.06(8) . . ?
C5 C10 C9 119.08(9) . . ?
O1 C21 N1 123.61(9) . . ?
O1 C21 C2 121.92(9) . . ?
N1 C21 C2 114.47(8) . . ?
C21 N1 C11 127.69(8) . . ?
C21 N1 H1N 116.7(10) . . ?
C11 N1 H1N 115.6(10) . . ?
C16 C11 C12 119.54(8) . . ?
C16 C11 N1 117.41(8) . . ?
C12 C11 N1 122.89(8) . . ?
C13 C12 C11 119.41(9) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.93(9) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
O14 C14 C15 124.40(9) . . ?
O14 C14 C13 115.83(8) . . ?
C15 C14 C13 119.76(8) . . ?
C14 O14 C141 116.64(8) . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C14 C15 C16 119.40(9) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 120.95(9) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.891(13) 2.476(14) 3.3053(11) 155.1(13) 1_455
C16 H16 O1 0.95 2.65 3.3567(12) 132 1_455
C141 H14B O14 0.98 2.70 3.4470(14) 133 2_656
C4 H4 Cg3 0.95 2.60 3.3446(11) 135 2_655
C8 H8 Cg3 0.95 2.62 3.3865(11) 138 2_765
C12 H12 Cg1 0.95 2.88 3.5199(11) 126 2_755
C13 H13 Cg2 0.95 2.95 3.5714(11) 124 2_755
C15 H15 Cg2 0.95 2.87 3.5330(11) 128 2_665
C16 H16 Cg1 0.95 2.95 3.5484(11) 122 2_665

_iucr_geom_hbonds_special_details 
;
Cg1, Cg2 and Cg3 are the centroids of the C1...C4,C9,C10, C5...C10 and 
C11...C16 rings respectively.
;

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

