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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_cd214722
_database_code_depnum_ccdc_archive 'CCDC 1047516'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   13.273(3)
_cell_length_b                   18.584(5)
_cell_length_c                   7.3811(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1820.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3079
_cell_measurement_theta_min      4.383
_cell_measurement_theta_max      51.692

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9074
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.885
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3298
_reflns_number_gt                2839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.949

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0566P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 989 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3298
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1447
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
N1 N 0.0713(3) 0.25329(18) 0.3536(6) 0.0356(9) Uani 1 1 d . . . . .
O1 O 0.1836(3) -0.15934(18) 0.2307(7) 0.0568(11) Uani 1 1 d . . . . .
C1 C 0.0756(4) 0.3132(2) 0.4650(7) 0.0411(11) Uani 1 1 d . . . . .
H1 H 0.0459 0.3561 0.4285 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1228(4) 0.3093(3) 0.6260(8) 0.0458(12) Uani 1 1 d . . . . .
H2 H 0.1273 0.3500 0.6987 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1654(4) 0.2439(3) 0.6852(8) 0.0478(12) Uani 1 1 d . . . . .
H3 H 0.1976 0.2417 0.7970 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1598(4) 0.1840(3) 0.5797(7) 0.0406(11) Uani 1 1 d . . . . .
H4 H 0.1877 0.1411 0.6204 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1123(3) 0.1865(2) 0.4102(7) 0.0343(10) Uani 1 1 d . . . . .
C6 C 0.0883(3) 0.1366(2) 0.2763(7) 0.0374(10) Uani 1 1 d . . . . .
C7 C 0.0322(4) 0.1736(2) 0.1430(7) 0.0403(11) Uani 1 1 d . . . . .
H7 H 0.0055 0.1530 0.0387 0.048 Uiso 1 1 calc R U . . .
C8 C 0.0232(4) 0.2445(2) 0.1909(7) 0.0394(11) Uani 1 1 d . . . . .
C9 C -0.0305(4) 0.3029(2) 0.0969(7) 0.0370(11) Uani 1 1 d . . . . .
C10 C -0.1293(4) 0.2936(3) 0.0530(9) 0.0495(13) Uani 1 1 d . . . . .
H10 H -0.1619 0.2518 0.0898 0.059 Uiso 1 1 calc R U . . .
C11 C -0.1836(4) 0.3453(3) -0.0463(10) 0.0579(16) Uani 1 1 d . . . . .
H11 H -0.2511 0.3376 -0.0734 0.070 Uiso 1 1 calc R U . . .
C12 C -0.1373(4) 0.4061(3) -0.1023(9) 0.0497(14) Uani 1 1 d . . . . .
H12 H -0.1735 0.4398 -0.1688 0.060 Uiso 1 1 calc R U . . .
C13 C -0.0354(4) 0.4194(2) -0.0620(7) 0.0387(11) Uani 1 1 d . . . . .
C14 C 0.0195(3) 0.3675(2) 0.0380(7) 0.0344(10) Uani 1 1 d . . . . .
C15 C 0.1242(4) 0.3806(2) 0.0666(7) 0.0422(11) Uani 1 1 d . . . . .
H15 H 0.1627 0.3467 0.1284 0.051 Uiso 1 1 calc R U . . .
C16 C 0.1681(4) 0.4414(3) 0.0049(8) 0.0493(13) Uani 1 1 d . . . . .
H16 H 0.2363 0.4491 0.0264 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1128(4) 0.4929(3) -0.0906(9) 0.0519(13) Uani 1 1 d . . . . .
H17 H 0.1439 0.5347 -0.1310 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0133(4) 0.4816(2) -0.1244(8) 0.0474(13) Uani 1 1 d . . . . .
H18 H -0.0230 0.5156 -0.1899 0.057 Uiso 1 1 calc R U . . .
C19 C 0.1125(4) 0.0589(2) 0.2716(7) 0.0361(10) Uani 1 1 d . . . . .
C20 C 0.2004(4) 0.0301(2) 0.3407(8) 0.0432(12) Uani 1 1 d . . . . .
H20 H 0.2466 0.0605 0.3969 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2216(4) -0.0426(2) 0.3285(8) 0.0460(12) Uani 1 1 d . . . . .
H21 H 0.2810 -0.0605 0.3780 0.055 Uiso 1 1 calc R U . . .
C22 C 0.1554(4) -0.0887(2) 0.2434(7) 0.0415(11) Uani 1 1 d . . . . .
C23 C 0.0672(4) -0.0617(2) 0.1730(8) 0.0451(12) Uani 1 1 d . . . . .
H23 H 0.0219 -0.0923 0.1157 0.054 Uiso 1 1 calc R U . . .
C24 C 0.0457(4) 0.0111(2) 0.1871(8) 0.0455(12) Uani 1 1 d . . . . .
H24 H -0.0144 0.0286 0.1395 0.055 Uiso 1 1 calc R U . . .
C25 C 0.1213(5) -0.2057(3) 0.1305(11) 0.0632(17) Uani 1 1 d . . . . .
H25A H 0.0547 -0.2053 0.1810 0.095 Uiso 1 1 calc R U . . .
H25B H 0.1480 -0.2537 0.1352 0.095 Uiso 1 1 calc R U . . .
H25C H 0.1187 -0.1898 0.0068 0.095 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
N1 C8 1.370(6) . ?
N1 C1 1.386(6) . ?
N1 C5 1.419(5) . ?
O1 C22 1.370(6) . ?
O1 C25 1.405(7) . ?
C1 C2 1.345(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.411(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(7) . ?
C6 C7 1.413(7) . ?
C6 C19 1.480(6) . ?
C7 C8 1.368(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.472(6) . ?
C9 C10 1.362(7) . ?
C9 C14 1.440(6) . ?
C10 C11 1.407(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.351(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(7) . ?
C12 H12 0.9300 . ?
C13 C18 1.401(7) . ?
C13 C14 1.417(6) . ?
C14 C15 1.426(7) . ?
C15 C16 1.351(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(8) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.381(7) . ?
C19 C24 1.401(7) . ?
C20 C21 1.383(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(7) . ?
C23 C24 1.387(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 129.5(4) . . ?
C8 N1 C5 109.4(4) . . ?
C1 N1 C5 120.8(4) . . ?
C22 O1 C25 117.6(4) . . ?
C2 C1 N1 120.0(4) . . ?
C2 C1 H1 120.0 . . ?
N1 C1 H1 120.0 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 135.7(4) . . ?
C6 C5 N1 106.6(4) . . ?
C4 C5 N1 117.6(4) . . ?
C5 C6 C7 106.9(4) . . ?
C5 C6 C19 128.1(4) . . ?
C7 C6 C19 125.0(5) . . ?
C8 C7 C6 109.6(5) . . ?
C8 C7 H7 125.2 . . ?
C6 C7 H7 125.2 . . ?
C7 C8 N1 107.5(4) . . ?
C7 C8 C9 129.1(5) . . ?
N1 C8 C9 123.4(4) . . ?
C10 C9 C14 118.6(4) . . ?
C10 C9 C8 119.0(4) . . ?
C14 C9 C8 122.3(4) . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C18 C13 C12 121.3(4) . . ?
C18 C13 C14 119.7(4) . . ?
C12 C13 C14 118.9(4) . . ?
C13 C14 C15 117.5(4) . . ?
C13 C14 C9 119.3(4) . . ?
C15 C14 C9 123.1(4) . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.1(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 121.0(5) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C24 117.0(4) . . ?
C20 C19 C6 123.5(4) . . ?
C24 C19 C6 119.4(4) . . ?
C19 C20 C21 121.7(4) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
O1 C22 C23 123.9(4) . . ?
O1 C22 C21 116.9(4) . . ?
C23 C22 C21 119.3(4) . . ?
C22 C23 C24 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 121.4(4) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 176.2(5) . . . . ?
C5 N1 C1 C2 2.8(7) . . . . ?
N1 C1 C2 C3 -2.0(8) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C3 C4 C5 C6 -175.5(5) . . . . ?
C3 C4 C5 N1 0.3(7) . . . . ?
C8 N1 C5 C6 0.4(5) . . . . ?
C1 N1 C5 C6 175.0(4) . . . . ?
C8 N1 C5 C4 -176.5(4) . . . . ?
C1 N1 C5 C4 -2.0(6) . . . . ?
C4 C5 C6 C7 175.3(5) . . . . ?
N1 C5 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 C19 -3.0(9) . . . . ?
N1 C5 C6 C19 -179.1(4) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C19 C6 C7 C8 179.4(4) . . . . ?
C6 C7 C8 N1 -0.8(6) . . . . ?
C6 C7 C8 C9 -178.3(5) . . . . ?
C1 N1 C8 C7 -173.7(5) . . . . ?
C5 N1 C8 C7 0.2(5) . . . . ?
C1 N1 C8 C9 4.0(7) . . . . ?
C5 N1 C8 C9 177.9(4) . . . . ?
C7 C8 C9 C10 53.4(8) . . . . ?
N1 C8 C9 C10 -123.8(6) . . . . ?
C7 C8 C9 C14 -122.0(6) . . . . ?
N1 C8 C9 C14 60.9(7) . . . . ?
C14 C9 C10 C11 -0.5(9) . . . . ?
C8 C9 C10 C11 -176.1(6) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C10 C11 C12 C13 -0.6(10) . . . . ?
C11 C12 C13 C18 178.2(6) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C18 C13 C14 C15 -1.6(7) . . . . ?
C12 C13 C14 C15 176.1(5) . . . . ?
C18 C13 C14 C9 -178.2(4) . . . . ?
C12 C13 C14 C9 -0.5(7) . . . . ?
C10 C9 C14 C13 0.5(7) . . . . ?
C8 C9 C14 C13 175.9(4) . . . . ?
C10 C9 C14 C15 -175.9(5) . . . . ?
C8 C9 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C16 2.0(7) . . . . ?
C9 C14 C15 C16 178.5(5) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 -0.8(9) . . . . ?
C16 C17 C18 C13 1.1(9) . . . . ?
C12 C13 C18 C17 -177.5(5) . . . . ?
C14 C13 C18 C17 0.1(8) . . . . ?
C5 C6 C19 C20 -34.8(8) . . . . ?
C7 C6 C19 C20 147.2(5) . . . . ?
C5 C6 C19 C24 147.7(5) . . . . ?
C7 C6 C19 C24 -30.2(7) . . . . ?
C24 C19 C20 C21 -0.4(8) . . . . ?
C6 C19 C20 C21 -177.9(5) . . . . ?
C19 C20 C21 C22 1.0(8) . . . . ?
C25 O1 C22 C23 3.9(8) . . . . ?
C25 O1 C22 C21 -174.5(6) . . . . ?
C20 C21 C22 O1 177.5(5) . . . . ?
C20 C21 C22 C23 -0.9(8) . . . . ?
O1 C22 C23 C24 -178.1(5) . . . . ?
C21 C22 C23 C24 0.2(8) . . . . ?
C22 C23 C24 C19 0.4(9) . . . . ?
C20 C19 C24 C23 -0.3(8) . . . . ?
C6 C19 C24 C23 177.3(5) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.050

_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_mo_dm15013_0m
_database_code_depnum_ccdc_archive 'CCDC 1047519'
_audit_update_record             
;
2015-02-05 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;
_audit_creation_date             2015-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H32 N, Cl'
_chemical_formula_sum            'C24 H32 Cl N'
_chemical_formula_weight         369.95
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.0083(10)
_cell_length_b                   8.9587(12)
_cell_length_c                   32.914(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2066.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3323
_cell_measurement_temperature    130
_cell_measurement_theta_max      24.642
_cell_measurement_theta_min      2.356
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1222 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            16772
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.237
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4041
_reflns_number_total             4731
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1480 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0952(3) 0.2677(2) 0.07219(7) 0.0201(5) Uani 1 1 d . . . . .
H1 H 0.9546 0.2795 0.0764 0.024 Uiso 1 1 calc R . . . .
C1 C 1.1271(5) 0.1333(3) 0.04653(9) 0.0264(7) Uani 1 1 d . . . . .
H1A H 1.2656 0.1159 0.0429 0.032 Uiso 1 1 calc R . . . .
H1B H 1.0688 0.1477 0.0194 0.032 Uiso 1 1 calc R . . . .
C2 C 1.0362(5) 0.0009(3) 0.06778(10) 0.0291(7) Uani 1 1 d . . . . .
H2A H 1.0612 -0.0906 0.0518 0.035 Uiso 1 1 calc R . . . .
H2B H 0.8963 0.0158 0.0689 0.035 Uiso 1 1 calc R . . . .
C3 C 1.1120(5) -0.0206(3) 0.11068(10) 0.0305(7) Uani 1 1 d . . . . .
H3A H 1.2483 -0.0493 0.1095 0.037 Uiso 1 1 calc R . . . .
H3B H 1.0410 -0.1024 0.1241 0.037 Uiso 1 1 calc R . . . .
C4 C 1.0906(5) 0.1228(3) 0.13553(9) 0.0287(7) Uani 1 1 d . . . . .
H4A H 0.9537 0.1460 0.1394 0.034 Uiso 1 1 calc R . . . .
H4B H 1.1495 0.1094 0.1626 0.034 Uiso 1 1 calc R . . . .
C5 C 1.1877(4) 0.2497(3) 0.11323(9) 0.0228(6) Uani 1 1 d . . . . .
H5 H 1.3238 0.2206 0.1087 0.027 Uiso 1 1 calc R . . . .
C6 C 1.1863(5) 0.4098(3) 0.13112(9) 0.0269(7) Uani 1 1 d . . . . .
H6 H 1.3184 0.4314 0.1410 0.032 Uiso 1 1 calc R . . . .
C7 C 1.1499(5) 0.5116(3) 0.09380(9) 0.0288(7) Uani 1 1 d . . . . .
H7A H 1.0197 0.5543 0.0949 0.035 Uiso 1 1 calc R . . . .
H7B H 1.2432 0.5945 0.0932 0.035 Uiso 1 1 calc R . . . .
C8 C 1.1724(4) 0.4126(3) 0.05630(8) 0.0215(6) Uani 1 1 d . . . . .
H8 H 1.3111 0.4007 0.0500 0.026 Uiso 1 1 calc R . . . .
C9 C 1.0676(4) 0.4620(3) 0.01832(9) 0.0220(6) Uani 1 1 d . . . . .
H9A H 0.9304 0.4740 0.0247 0.026 Uiso 1 1 calc R . . . .
H9B H 1.0795 0.3835 -0.0027 0.026 Uiso 1 1 calc R . . . .
C10 C 1.1444(4) 0.6080(3) 0.00150(8) 0.0230(6) Uani 1 1 d . . . . .
H10A H 1.2845 0.6002 -0.0017 0.028 Uiso 1 1 calc R . . . .
H10B H 1.1179 0.6892 0.0211 0.028 Uiso 1 1 calc R . . . .
C11 C 1.0551(4) 0.6475(3) -0.03948(9) 0.0243(6) Uani 1 1 d . . . . .
H11A H 1.0768 0.5644 -0.0588 0.029 Uiso 1 1 calc R . . . .
H11B H 0.9156 0.6595 -0.0360 0.029 Uiso 1 1 calc R . . . .
C12 C 1.1373(5) 0.7898(3) -0.05713(10) 0.0328(7) Uani 1 1 d . . . . .
H12A H 1.0747 0.8118 -0.0831 0.049 Uiso 1 1 calc GR . . . .
H12B H 1.2746 0.7771 -0.0616 0.049 Uiso 1 1 calc GR . . . .
H12C H 1.1159 0.8724 -0.0382 0.049 Uiso 1 1 calc GR . . . .
C13 C 1.0531(5) 0.4299(3) 0.16670(9) 0.0268(7) Uani 1 1 d . . . . .
C14 C 1.1204(5) 0.4018(4) 0.20576(9) 0.0323(7) Uani 1 1 d . . . . .
H14 H 1.2518 0.3797 0.2095 0.039 Uiso 1 1 calc R . . . .
C15 C 1.0009(5) 0.4052(4) 0.23926(9) 0.0334(7) Uani 1 1 d . . . . .
H15 H 1.0502 0.3838 0.2655 0.040 Uiso 1 1 calc R . . . .
C16 C 0.8086(5) 0.4398(3) 0.23453(9) 0.0284(7) Uani 1 1 d . . . . .
C17 C 0.7423(5) 0.4715(4) 0.19556(9) 0.0323(7) Uani 1 1 d . . . . .
H17 H 0.6121 0.4977 0.1918 0.039 Uiso 1 1 calc R . . . .
C18 C 0.8623(5) 0.4656(4) 0.16232(9) 0.0311(7) Uani 1 1 d . . . . .
H18 H 0.8130 0.4864 0.1360 0.037 Uiso 1 1 calc R . . . .
C19 C 0.6741(5) 0.4388(4) 0.26957(9) 0.0288(7) Uani 1 1 d . . . . .
C20 C 0.6774(6) 0.3215(4) 0.29753(9) 0.0354(8) Uani 1 1 d . . . . .
H20 H 0.7691 0.2440 0.2949 0.042 Uiso 1 1 calc R . . . .
C21 C 0.5465(6) 0.3184(4) 0.32908(11) 0.0420(9) Uani 1 1 d . . . . .
H21 H 0.5469 0.2369 0.3475 0.050 Uiso 1 1 calc R . . . .
C22 C 0.4158(5) 0.4316(5) 0.33412(11) 0.0448(9) Uani 1 1 d . . . . .
H22 H 0.3273 0.4290 0.3560 0.054 Uiso 1 1 calc R . . . .
C23 C 0.4154(6) 0.5495(5) 0.30685(11) 0.0435(9) Uani 1 1 d . . . . .
H23 H 0.3276 0.6292 0.3103 0.052 Uiso 1 1 calc R . . . .
C24 C 0.5414(5) 0.5519(4) 0.27469(10) 0.0351(8) Uani 1 1 d . . . . .
H24 H 0.5373 0.6321 0.2558 0.042 Uiso 1 1 calc R . . . .
Cl1 Cl 0.65958(10) 0.28862(8) 0.07239(2) 0.02675(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.488(3) . ?
N1 C5 1.507(4) . ?
N1 C8 1.500(3) . ?
C1 C2 1.517(4) . ?
C2 C3 1.521(5) . ?
C3 C4 1.530(4) . ?
C4 C5 1.515(4) . ?
C5 C6 1.550(4) . ?
C6 C7 1.551(4) . ?
C6 C13 1.508(4) . ?
C7 C8 1.528(4) . ?
C8 C9 1.516(4) . ?
C9 C10 1.519(4) . ?
C10 C11 1.528(4) . ?
C11 C12 1.515(4) . ?
C13 C14 1.392(4) . ?
C13 C18 1.382(5) . ?
C14 C15 1.385(5) . ?
C15 C16 1.391(5) . ?
C16 C17 1.393(4) . ?
C16 C19 1.490(4) . ?
C17 C18 1.381(5) . ?
C19 C20 1.397(4) . ?
C19 C24 1.386(5) . ?
C20 C21 1.386(5) . ?
C21 C22 1.376(6) . ?
C22 C23 1.386(6) . ?
C23 C24 1.379(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 110.9(2) . . ?
C1 N1 C8 116.6(2) . . ?
C8 N1 C5 104.5(2) . . ?
N1 C1 C2 107.9(2) . . ?
C1 C2 C3 112.3(3) . . ?
C2 C3 C4 110.9(3) . . ?
C5 C4 C3 109.1(2) . . ?
N1 C5 C4 108.7(2) . . ?
N1 C5 C6 103.8(2) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C7 104.1(2) . . ?
C13 C6 C5 114.1(2) . . ?
C13 C6 C7 116.3(3) . . ?
C8 C7 C6 106.3(2) . . ?
N1 C8 C7 100.6(2) . . ?
N1 C8 C9 111.4(2) . . ?
C9 C8 C7 116.5(2) . . ?
C8 C9 C10 112.4(2) . . ?
C9 C10 C11 112.1(2) . . ?
C12 C11 C10 112.2(3) . . ?
C14 C13 C6 119.1(3) . . ?
C18 C13 C6 123.0(3) . . ?
C18 C13 C14 117.8(3) . . ?
C15 C14 C13 121.8(3) . . ?
C14 C15 C16 120.1(3) . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 C19 121.6(3) . . ?
C17 C16 C19 120.2(3) . . ?
C18 C17 C16 121.2(3) . . ?
C17 C18 C13 121.0(3) . . ?
C20 C19 C16 120.3(3) . . ?
C24 C19 C16 120.9(3) . . ?
C24 C19 C20 118.7(3) . . ?
C21 C20 C19 119.9(3) . . ?
C22 C21 C20 121.0(4) . . ?
C21 C22 C23 119.0(3) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C19 120.8(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
N1 C1 C2 C3 -56.2(3) . . . . ?
N1 C5 C6 C7 -16.7(3) . . . . ?
N1 C5 C6 C13 111.1(3) . . . . ?
N1 C8 C9 C10 -179.6(2) . . . . ?
C1 N1 C5 C4 -64.6(3) . . . . ?
C1 N1 C5 C6 166.0(2) . . . . ?
C1 N1 C8 C7 -168.7(2) . . . . ?
C1 N1 C8 C9 67.2(3) . . . . ?
C1 C2 C3 C4 54.3(4) . . . . ?
C2 C3 C4 C5 -55.1(4) . . . . ?
C3 C4 C5 N1 59.6(3) . . . . ?
C3 C4 C5 C6 179.1(3) . . . . ?
C4 C5 C6 C7 -138.7(3) . . . . ?
C4 C5 C6 C13 -10.8(4) . . . . ?
C5 N1 C1 C2 61.3(3) . . . . ?
C5 N1 C8 C7 -45.8(3) . . . . ?
C5 N1 C8 C9 -170.0(2) . . . . ?
C5 C6 C7 C8 -11.1(3) . . . . ?
C5 C6 C13 C14 88.8(4) . . . . ?
C5 C6 C13 C18 -86.8(4) . . . . ?
C6 C7 C8 N1 34.6(3) . . . . ?
C6 C7 C8 C9 155.1(3) . . . . ?
C6 C13 C14 C15 -174.1(3) . . . . ?
C6 C13 C18 C17 174.9(3) . . . . ?
C7 C6 C13 C14 -149.9(3) . . . . ?
C7 C6 C13 C18 34.5(4) . . . . ?
C7 C8 C9 C10 65.8(3) . . . . ?
C8 N1 C1 C2 -179.3(2) . . . . ?
C8 N1 C5 C4 169.0(2) . . . . ?
C8 N1 C5 C6 39.5(3) . . . . ?
C8 C9 C10 C11 173.1(2) . . . . ?
C9 C10 C11 C12 -177.6(2) . . . . ?
C13 C6 C7 C8 -137.6(3) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C13 C18 C17 -0.7(5) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C14 C15 C16 C19 177.6(3) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C15 C16 C19 C20 -44.7(4) . . . . ?
C15 C16 C19 C24 136.5(3) . . . . ?
C16 C17 C18 C13 -0.9(5) . . . . ?
C16 C19 C20 C21 -177.4(3) . . . . ?
C16 C19 C24 C23 179.1(3) . . . . ?
C17 C16 C19 C20 133.3(3) . . . . ?
C17 C16 C19 C24 -45.5(5) . . . . ?
C18 C13 C14 C15 1.7(5) . . . . ?
C19 C16 C17 C18 -176.6(3) . . . . ?
C19 C20 C21 C22 -1.9(5) . . . . ?
C20 C19 C24 C23 0.3(5) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
C21 C22 C23 C24 1.3(6) . . . . ?
C22 C23 C24 C19 -1.7(6) . . . . ?
C24 C19 C20 C21 1.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
