# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ortho_a
_database_code_depnum_ccdc_archive 'CCDC 1580560'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N'
_chemical_formula_weight         313.42

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   18.820(12)
_cell_length_b                   25.412(17)
_cell_length_c                   7.492(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3583(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1749
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      22.30

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10931
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.346
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.889
_reflns_number_total             3308
_reflns_number_gt                2270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_max     0.715
_reflns_Friedel_fraction_full    0.758

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0652P)²+0.3832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 692 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.81568(16) 0.34700(12) 0.2287(4) 0.0326(8) Uani 1 1 d . . . . .
C1 C 0.8693(2) 0.32928(18) 0.1025(6) 0.0466(12) Uani 1 1 d . . . . .
H1A H 0.9056 0.3566 0.0886 0.070 Uiso 1 1 calc R U . . .
H1B H 0.8469 0.3223 -0.0132 0.070 Uiso 1 1 calc R U . . .
H1C H 0.8914 0.2970 0.1471 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8365(2) 0.37563(14) 0.3817(5) 0.0296(9) Uani 1 1 d . . . . .
C3 C 0.9083(2) 0.38175(15) 0.4301(6) 0.0338(9) Uani 1 1 d . . . . .
H3A H 0.9444 0.3663 0.3585 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9269(2) 0.41004(16) 0.5809(6) 0.0383(11) Uani 1 1 d . . . . .
H4A H 0.9757 0.4137 0.6109 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8759(2) 0.43327(15) 0.6893(5) 0.0359(10) Uani 1 1 d . . . . .
C6 C 0.8050(2) 0.42619(14) 0.6416(5) 0.0319(9) Uani 1 1 d . . . . .
H6A H 0.7692 0.4411 0.7154 0.038 Uiso 1 1 calc R U . . .
C7 C 0.78428(19) 0.39820(14) 0.4900(5) 0.0265(8) Uani 1 1 d . . . . .
C8 C 0.8953(2) 0.46547(17) 0.8527(7) 0.0532(13) Uani 1 1 d . . . . .
H8A H 0.9467 0.4634 0.8730 0.080 Uiso 1 1 calc R U . . .
H8B H 0.8702 0.4516 0.9572 0.080 Uiso 1 1 calc R U . . .
H8C H 0.8817 0.5023 0.8336 0.080 Uiso 1 1 calc R U . . .
C9 C 0.7498(2) 0.32019(14) 0.2341(5) 0.0289(8) Uani 1 1 d . . . . .
C10 C 0.7377(2) 0.27361(16) 0.1402(5) 0.0351(9) Uani 1 1 d . . . . .
H10A H 0.7748 0.2590 0.0698 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6726(2) 0.24826(16) 0.1478(6) 0.0382(10) Uani 1 1 d . . . . .
H11A H 0.6662 0.2163 0.0843 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6165(2) 0.26889(15) 0.2468(5) 0.0325(9) Uani 1 1 d . . . . .
C13 C 0.62916(19) 0.31533(14) 0.3418(5) 0.0280(8) Uani 1 1 d . . . . .
H13A H 0.5917 0.3296 0.4117 0.034 Uiso 1 1 calc R U . . .
C14 C 0.69427(19) 0.34173(15) 0.3387(5) 0.0268(8) Uani 1 1 d . . . . .
C15 C 0.5440(2) 0.24277(16) 0.2494(6) 0.0421(11) Uani 1 1 d . . . . .
H15A H 0.5455 0.2105 0.1778 0.063 Uiso 1 1 calc R U . . .
H15B H 0.5086 0.2669 0.1993 0.063 Uiso 1 1 calc R U . . .
H15C H 0.5311 0.2341 0.3726 0.063 Uiso 1 1 calc R U . . .
C16 C 0.70616(18) 0.39487(14) 0.4320(5) 0.0263(8) Uani 1 1 d . . . . .
C17 C 0.6930(2) 0.43931(16) 0.2949(6) 0.0433(12) Uani 1 1 d . . . . .
H17A H 0.6446 0.4365 0.2481 0.065 Uiso 1 1 calc R U . . .
H17B H 0.7271 0.4361 0.1965 0.065 Uiso 1 1 calc R U . . .
H17C H 0.6991 0.4735 0.3532 0.065 Uiso 1 1 calc R U . . .
C18 C 0.65691(19) 0.39864(14) 0.5950(5) 0.0301(9) Uani 1 1 d . . . . .
C19 C 0.6045(2) 0.43680(17) 0.6150(7) 0.0476(12) Uani 1 1 d . . . . .
H19A H 0.5987 0.4636 0.5277 0.057 Uiso 1 1 calc R U . . .
C20 C 0.5595(2) 0.4352(2) 0.7688(9) 0.0621(16) Uani 1 1 d . . . . .
H20A H 0.5237 0.4612 0.7825 0.075 Uiso 1 1 calc R U . . .
C21 C 0.5669(3) 0.3974(2) 0.8955(7) 0.0625(16) Uani 1 1 d . . . . .
H21A H 0.5358 0.3966 0.9955 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6194(2) 0.3605(2) 0.8781(6) 0.0538(13) Uani 1 1 d . . . . .
H22A H 0.6255 0.3344 0.9677 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6636(2) 0.36106(17) 0.7300(5) 0.0387(10) Uani 1 1 d . . . . .
H23A H 0.6996 0.3350 0.7200 0.046 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 C2 1.413(5) . ?
N1 C9 1.415(5) . ?
N1 C1 1.454(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.397(5) . ?
C2 C3 1.409(5) . ?
C3 C4 1.384(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.390(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(5) . ?
C5 C8 1.517(6) . ?
C6 C7 1.395(5) . ?
C6 H6A 0.9500 . ?
C7 C16 1.536(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.395(5) . ?
C9 C14 1.417(5) . ?
C10 C11 1.385(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.393(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.398(5) . ?
C12 C15 1.518(5) . ?
C13 C14 1.397(5) . ?
C13 H13A 0.9500 . ?
C14 C16 1.537(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.536(5) . ?
C16 C17 1.546(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.391(5) . ?
C18 C23 1.396(6) . ?
C19 C20 1.430(8) . ?
C19 H19A 0.9500 . ?
C20 C21 1.357(7) . ?
C20 H20A 0.9500 . ?
C21 C22 1.369(7) . ?
C21 H21A 0.9500 . ?
C22 C23 1.388(6) . ?
C22 H22A 0.9500 . ?
C23 H23A 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 N1 C9 117.9(3) . . ?
C2 N1 C1 119.7(3) . . ?
C9 N1 C1 118.5(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.7(4) . . ?
C7 C2 N1 119.2(3) . . ?
C3 C2 N1 122.1(3) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 117.2(4) . . ?
C4 C5 C8 122.3(4) . . ?
C6 C5 C8 120.5(4) . . ?
C5 C6 C7 122.8(4) . . ?
C5 C6 H6A 118.6 . . ?
C7 C6 H6A 118.6 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 C16 121.7(3) . . ?
C2 C7 C16 119.1(3) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 122.5(3) . . ?
C10 C9 C14 119.1(3) . . ?
N1 C9 C14 118.4(3) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10A 119.4 . . ?
C9 C10 H10A 119.4 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11A 119.4 . . ?
C12 C11 H11A 119.4 . . ?
C11 C12 C13 117.4(3) . . ?
C11 C12 C15 121.6(4) . . ?
C13 C12 C15 121.0(4) . . ?
C14 C13 C12 123.1(3) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C9 118.1(3) . . ?
C13 C14 C16 122.8(3) . . ?
C9 C14 C16 118.9(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 C16 C18 110.4(3) . . ?
C7 C16 C14 108.5(3) . . ?
C18 C16 C14 109.2(3) . . ?
C7 C16 C17 107.5(3) . . ?
C18 C16 C17 112.7(3) . . ?
C14 C16 C17 108.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 117.6(4) . . ?
C19 C18 C16 123.8(4) . . ?
C23 C18 C16 118.6(3) . . ?
C18 C19 C20 119.1(5) . . ?
C18 C19 H19A 120.5 . . ?
C20 C19 H19A 120.5 . . ?
C21 C20 C19 121.6(4) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C20 C21 C22 119.4(5) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C21 C22 C23 120.1(5) . . ?
C21 C22 H22A 119.9 . . ?
C23 C22 H22A 119.9 . . ?
C22 C23 C18 122.1(4) . . ?
C22 C23 H23A 118.9 . . ?
C18 C23 H23A 118.9 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_JL023_iba2
_database_code_depnum_ccdc_archive 'CCDC 1580561'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br N'
_chemical_formula_weight         392.32

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   20.530(13)
_cell_length_b                   25.541(14)
_cell_length_c                   7.450(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3906(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5456
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      24.29

_exptl_crystal_description       SHARD
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.109
_shelx_estimated_absorpt_T_min   0.227
_shelx_estimated_absorpt_T_max   0.678
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27208
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.1183
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.595
_diffrn_reflns_theta_max         26.828
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3953
_reflns_number_gt                2843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.192(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
N1 N 0.3266(2) 0.34035(18) 0.0416(6) 0.0304(11) Uani 1 1 d . . . . .
C1 C 0.3740(3) 0.3180(3) -0.0820(9) 0.0498(18) Uani 1 1 d . . . . .
H1A H 0.4092 0.3433 -0.1023 0.075 Uiso 1 1 calc R U . . .
H1B H 0.3527 0.3100 -0.1963 0.075 Uiso 1 1 calc R U . . .
H1C H 0.3921 0.2859 -0.0304 0.075 Uiso 1 1 calc R U . . .
C2 C 0.2631(2) 0.3191(2) 0.0456(7) 0.0268(11) Uani 1 1 d . . . . .
C3 C 0.2465(3) 0.2733(2) -0.0495(7) 0.0313(13) Uani 1 1 d . . . . .
H3A H 0.2789 0.2556 -0.1176 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1835(3) 0.2537(2) -0.0448(7) 0.0332(13) Uani 1 1 d . . . . .
H4A H 0.1734 0.2228 -0.1100 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1346(3) 0.2784(2) 0.0532(7) 0.0284(12) Uani 1 1 d . . . . .
C6 C 0.1515(2) 0.3233(2) 0.1489(7) 0.0239(11) Uani 1 1 d . . . . .
H6A H 0.1189 0.3405 0.2173 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2148(2) 0.34408(19) 0.1480(7) 0.0212(11) Uani 1 1 d . . . . .
C8 C 0.0646(3) 0.2583(2) 0.0527(8) 0.0399(15) Uani 1 1 d . . . . .
H8A H 0.0638 0.2223 0.0074 0.060 Uiso 1 1 calc R U . . .
H8B H 0.0379 0.2806 -0.0249 0.060 Uiso 1 1 calc R U . . .
H8C H 0.0472 0.2591 0.1752 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3488(2) 0.3689(2) 0.1924(7) 0.0284(12) Uani 1 1 d . . . . .
C10 C 0.4148(2) 0.3712(2) 0.2408(8) 0.0349(14) Uani 1 1 d . . . . .
H10A H 0.4462 0.3524 0.1727 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4347(2) 0.4005(2) 0.3861(13) 0.0405(14) Uani 1 1 d . . . . .
H11A H 0.4798 0.4022 0.4140 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3903(3) 0.4280(2) 0.4941(8) 0.0365(14) Uani 1 1 d . . . . .
C13 C 0.3240(3) 0.4239(2) 0.4471(8) 0.0318(13) Uani 1 1 d . . . . .
H13A H 0.2926 0.4413 0.5190 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3029(2) 0.3953(2) 0.2996(7) 0.0245(12) Uani 1 1 d . . . . .
C15 C 0.4110(3) 0.4609(3) 0.6539(10) 0.0571(19) Uani 1 1 d . . . . .
H15A H 0.3980 0.4974 0.6342 0.086 Uiso 1 1 calc R U . . .
H15B H 0.4584 0.4590 0.6677 0.086 Uiso 1 1 calc R U . . .
H15C H 0.3899 0.4476 0.7628 0.086 Uiso 1 1 calc R U . . .
C16 C 0.2313(2) 0.3966(2) 0.2402(7) 0.0226(11) Uani 1 1 d . . . . .
C17 C 0.2245(2) 0.4413(2) 0.0988(7) 0.0294(12) Uani 1 1 d . . . . .
H17A H 0.2375 0.4747 0.1530 0.044 Uiso 1 1 calc R U . . .
H17B H 0.1790 0.4436 0.0591 0.044 Uiso 1 1 calc R U . . .
H17C H 0.2525 0.4338 -0.0044 0.044 Uiso 1 1 calc R U . . .
C18 C 0.1867(2) 0.40475(17) 0.4015(8) 0.0209(11) Uani 1 1 d . . . . .
C19 C 0.1426(2) 0.44650(19) 0.4161(7) 0.0245(12) Uani 1 1 d . . . . .
H19A H 0.1416 0.4728 0.3260 0.029 Uiso 1 1 calc R U . . .
C20 C 0.1002(2) 0.4497(2) 0.5612(7) 0.0263(12) Uani 1 1 d . . . . .
H20A H 0.0710 0.4783 0.5714 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1009(2) 0.4110(2) 0.6904(7) 0.0266(12) Uani 1 1 d . . . . .
C22 C 0.1459(3) 0.3693(2) 0.6826(7) 0.0297(12) Uani 1 1 d . . . . .
H22A H 0.1472 0.3435 0.7741 0.036 Uiso 1 1 calc R U . . .
C23 C 0.1880(2) 0.3671(2) 0.5386(7) 0.0278(12) Uani 1 1 d . . . . .
H23A H 0.2187 0.3394 0.5320 0.033 Uiso 1 1 calc R U . . .
Br1 Br 0.03858(2) 0.41312(2) 0.87885(12) 0.04188(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 C9 1.414(7) . ?
N1 C2 1.413(7) . ?
N1 C1 1.456(7) . ?
C2 C7 1.405(7) . ?
C2 C3 1.409(7) . ?
C3 C4 1.389(8) . ?
C4 C5 1.391(8) . ?
C5 C6 1.394(7) . ?
C5 C8 1.526(7) . ?
C6 C7 1.404(6) . ?
C7 C16 1.545(7) . ?
C9 C10 1.404(7) . ?
C9 C14 1.408(7) . ?
C10 C11 1.378(10) . ?
C11 C12 1.403(9) . ?
C12 C13 1.408(8) . ?
C12 C15 1.518(9) . ?
C13 C14 1.388(7) . ?
C14 C16 1.535(7) . ?
C16 C18 1.525(7) . ?
C16 C17 1.559(7) . ?
C18 C23 1.402(7) . ?
C18 C19 1.404(6) . ?
C19 C20 1.390(7) . ?
C20 C21 1.379(7) . ?
C21 C22 1.411(7) . ?
C21 Br1 1.900(5) . ?
C22 C23 1.379(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C2 118.6(4) . . ?
C9 N1 C1 119.3(4) . . ?
C2 N1 C1 118.7(5) . . ?
C7 C2 C3 118.7(5) . . ?
C7 C2 N1 119.2(5) . . ?
C3 C2 N1 122.1(5) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C4 C5 121.5(5) . . ?
C4 C5 C6 117.5(5) . . ?
C4 C5 C8 121.7(5) . . ?
C6 C5 C8 120.8(5) . . ?
C5 C6 C7 122.6(5) . . ?
C6 C7 C2 118.9(5) . . ?
C6 C7 C16 122.0(4) . . ?
C2 C7 C16 118.8(4) . . ?
C10 C9 C14 118.7(5) . . ?
C10 C9 N1 122.4(5) . . ?
C14 C9 N1 118.8(5) . . ?
C11 C10 C9 120.7(5) . . ?
C10 C11 C12 122.0(5) . . ?
C11 C12 C13 116.6(5) . . ?
C11 C12 C15 123.0(6) . . ?
C13 C12 C15 120.4(6) . . ?
C14 C13 C12 122.5(5) . . ?
C13 C14 C9 119.5(5) . . ?
C13 C14 C16 121.1(5) . . ?
C9 C14 C16 119.2(5) . . ?
C18 C16 C14 110.5(4) . . ?
C18 C16 C7 109.7(4) . . ?
C14 C16 C7 108.6(4) . . ?
C18 C16 C17 112.2(4) . . ?
C14 C16 C17 107.3(4) . . ?
C7 C16 C17 108.4(4) . . ?
C23 C18 C19 118.4(5) . . ?
C23 C18 C16 118.0(4) . . ?
C19 C18 C16 123.5(5) . . ?
C20 C19 C18 120.6(5) . . ?
C21 C20 C19 119.7(5) . . ?
C20 C21 C22 121.2(5) . . ?
C20 C21 Br1 119.3(4) . . ?
C22 C21 Br1 119.5(4) . . ?
C23 C22 C21 118.3(5) . . ?
C22 C23 C18 121.8(5) . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_JL024_a
_database_code_depnum_ccdc_archive 'CCDC 1580565'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N'
_chemical_formula_weight         299.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   8.0404(8)
_cell_length_b                   13.3233(17)
_cell_length_c                   15.2895(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1637.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15803
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.027
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1980
_reflns_number_gt                1641
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+3.1765P] 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         1980
_refine_ls_number_parameters     130
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.1977
_refine_ls_wR_factor_gt          0.1908
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.175
_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 0.4740(4) 0.2500 0.54190(19) 0.0189(6) Uani 1 2 d S T P . .
C1 C 0.3293(5) 0.2500 0.4843(2) 0.0235(8) Uani 1 2 d DS T P . .
H1A H 0.225(4) 0.2500 0.518(3) 0.035 Uiso 1 2 d DS U P . .
H1B H 0.338(4) 0.1896(18) 0.4483(19) 0.035 Uiso 1 1 d D U . . .
C2 C 0.5189(3) 0.33959(18) 0.58446(15) 0.0179(5) Uani 1 1 d . . . . .
C3 C 0.4161(3) 0.4240(2) 0.58473(16) 0.0229(6) Uani 1 1 d . . . . .
H3 H 0.3137 0.4231 0.5538 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4644(4) 0.5095(2) 0.63064(18) 0.0273(6) Uani 1 1 d . . . . .
H4 H 0.3961 0.5677 0.6296 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6113(4) 0.5103(2) 0.67774(18) 0.0296(6) Uani 1 1 d . . . . .
H5 H 0.6416 0.5679 0.7107 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7145(3) 0.4264(2) 0.67673(16) 0.0244(6) Uani 1 1 d . . . . .
H6 H 0.8153 0.4274 0.7091 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6725(3) 0.34137(19) 0.62905(14) 0.0183(5) Uani 1 1 d . . . . .
C8 C 0.9334(5) 0.2500 0.6799(3) 0.0285(9) Uani 1 2 d DS T P . .
H8A H 0.895(6) 0.2500 0.7408(17) 0.043 Uiso 1 2 d DS U P . .
H8B H 1.001(4) 0.1896(19) 0.668(2) 0.043 Uiso 1 1 d D U . . .
C9 C 0.7843(4) 0.2500 0.6165(2) 0.0193(7) Uani 1 2 d S T P . .
C10 C 0.8534(4) 0.2500 0.5219(2) 0.0179(7) Uani 1 2 d S T P . .
C11 C 0.8906(3) 0.1604(2) 0.47911(17) 0.0221(5) Uani 1 1 d . . . . .
H11 H 0.8665 0.0982 0.5069 0.027 Uiso 1 1 calc R U . . .
C12 C 0.9626(3) 0.1606(2) 0.39611(17) 0.0229(6) Uani 1 1 d . . . . .
H12 H 0.9868 0.0985 0.3683 0.027 Uiso 1 1 calc R U . . .
C13 C 0.9998(4) 0.2500 0.3531(2) 0.0210(7) Uani 1 2 d S T P . .
C14 C 1.0788(5) 0.2500 0.2638(3) 0.0267(8) Uani 1 2 d DS T P . .
H14A H 0.998(5) 0.2500 0.216(2) 0.040 Uiso 1 2 d DS U P . .
H14B H 1.150(4) 0.1912(19) 0.254(2) 0.040 Uiso 1 1 d D 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 C2 1.407(3) . ?
N1 C2 1.407(3) 7_565 ?
N1 C1 1.459(4) . ?
C1 H1A 0.988(19) . ?
C1 H1B 0.977(17) . ?
C2 C3 1.396(4) . ?
C2 C7 1.411(3) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C9 1.526(3) . ?
C8 C9 1.542(5) . ?
C8 H8A 0.983(19) . ?
C8 H8B 0.986(18) . ?
C9 C7 1.526(3) 7_565 ?
C9 C10 1.549(5) . ?
C10 C11 1.394(3) 7_565 ?
C10 C11 1.394(3) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C12 1.393(3) 7_565 ?
C13 C14 1.506(5) . ?
C14 H14A 0.977(19) . ?
C14 H14B 0.980(18) . ?

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 N1 C2 116.1(3) . 7_565 ?
C2 N1 C1 118.94(15) . . ?
C2 N1 C1 118.93(15) 7_565 . ?
N1 C1 H1A 111(3) . . ?
N1 C1 H1B 107(2) . . ?
H1A C1 H1B 111(2) . . ?
C3 C2 N1 122.2(2) . . ?
C3 C2 C7 120.2(2) . . ?
N1 C2 C7 117.6(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 118.7(2) . . ?
C6 C7 C9 125.0(2) . . ?
C2 C7 C9 116.2(2) . . ?
C9 C8 H8A 110(3) . . ?
C9 C8 H8B 108(2) . . ?
H8A C8 H8B 110(3) . . ?
C7 C9 C7 105.9(3) . 7_565 ?
C7 C9 C8 112.28(19) . . ?
C7 C9 C8 112.28(19) 7_565 . ?
C7 C9 C10 109.21(18) . . ?
C7 C9 C10 109.21(18) 7_565 . ?
C8 C9 C10 107.9(3) . . ?
C11 C10 C11 117.9(3) 7_565 . ?
C11 C10 C9 121.00(16) 7_565 . ?
C11 C10 C9 121.00(16) . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C12 117.5(3) 7_565 . ?
C12 C13 C14 121.23(16) 7_565 . ?
C12 C13 C14 121.23(16) . . ?
C13 C14 H14A 113(3) . . ?
C13 C14 H14B 113(2) . . ?
H14A C14 H14B 106(3) . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_JL019_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1580564'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 N'
_chemical_formula_weight         389.51

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/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'
'-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                   23.643(4)
_cell_length_b                   6.2144(9)
_cell_length_c                   29.822(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.394(6)
_cell_angle_gamma                90
_cell_volume                     4224.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2176
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      22.28

_exptl_crystal_description       NEEDLES
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15129
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.416
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4838
_reflns_number_gt                2608
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0828P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4838
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1690
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.32361(8) 0.7225(3) 0.29961(7) 0.0228(5) Uani 1 1 d . . . . .
C1 C 0.29218(11) 0.5332(4) 0.27658(9) 0.0328(7) Uani 1 1 d . . . . .
H1A H 0.3173 0.4537 0.2609 0.049 Uiso 1 1 calc R U . . .
H1B H 0.2563 0.5788 0.2536 0.049 Uiso 1 1 calc R U . . .
H1C H 0.2819 0.4402 0.2998 0.049 Uiso 1 1 calc R U . . .
C2 C 0.30128(10) 0.8275(4) 0.33312(8) 0.0209(5) Uani 1 1 d . . . . .
C3 C 0.24939(11) 0.7606(4) 0.34299(9) 0.0297(6) Uani 1 1 d . . . . .
H3A H 0.2300 0.6346 0.3287 0.036 Uiso 1 1 calc R U . . .
C4 C 0.22606(11) 0.8765(5) 0.37347(9) 0.0331(7) Uani 1 1 d . . . . .
H4A H 0.1915 0.8256 0.3805 0.040 Uiso 1 1 calc R U . . .
C5 C 0.25181(11) 1.0649(4) 0.39395(9) 0.0291(6) Uani 1 1 d . . . . .
C6 C 0.30489(10) 1.1272(4) 0.38498(8) 0.0243(6) Uani 1 1 d . . . . .
H6A H 0.3238 1.2544 0.3991 0.029 Uiso 1 1 calc R U . . .
C7 C 0.33071(9) 1.0088(4) 0.35609(8) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.22419(12) 1.1989(5) 0.42485(10) 0.0459(8) Uani 1 1 d . . . . .
H8A H 0.1906 1.1216 0.4304 0.069 Uiso 1 1 calc R U . . .
H8B H 0.2110 1.3365 0.4096 0.069 Uiso 1 1 calc R U . . .
H8C H 0.2532 1.2256 0.4546 0.069 Uiso 1 1 calc R U . . .
C9 C 0.35318(10) 0.8518(4) 0.27434(8) 0.0227(6) Uani 1 1 d . . . . .
C10 C 0.35336(11) 0.8056(4) 0.22812(9) 0.0306(6) Uani 1 1 d . . . . .
H10A H 0.3345 0.6794 0.2134 0.037 Uiso 1 1 calc R U . . .
C11 C 0.38062(11) 0.9421(5) 0.20408(9) 0.0367(7) Uani 1 1 d . . . . .
H11A H 0.3812 0.9055 0.1733 0.044 Uiso 1 1 calc R U . . .
C12 C 0.40715(11) 1.1310(5) 0.22352(9) 0.0318(6) Uani 1 1 d . . . . .
C13 C 0.40779(10) 1.1732(4) 0.26948(9) 0.0261(6) Uani 1 1 d . . . . .
H13A H 0.4259 1.3020 0.2835 0.031 Uiso 1 1 calc R U . . .
C14 C 0.38321(9) 1.0358(4) 0.29580(8) 0.0197(5) Uani 1 1 d . . . . .
C15 C 0.43339(12) 1.2877(5) 0.19609(10) 0.0464(8) Uani 1 1 d . . . . .
H15A H 0.4597 1.2107 0.1812 0.070 Uiso 1 1 calc R U . . .
H15B H 0.4556 1.3978 0.2170 0.070 Uiso 1 1 calc R U . . .
H15C H 0.4020 1.3564 0.1722 0.070 Uiso 1 1 calc R U . . .
C16 C 0.39027(9) 1.0653(4) 0.34793(8) 0.0185(5) Uani 1 1 d . . . . .
C17 C 0.41119(10) 1.2922(4) 0.36510(9) 0.0247(6) Uani 1 1 d . . . . .
H17A H 0.3828 1.3987 0.3483 0.037 Uiso 1 1 calc R U . . .
H17B H 0.4496 1.3196 0.3595 0.037 Uiso 1 1 calc R U . . .
H17C H 0.4145 1.3030 0.3985 0.037 Uiso 1 1 calc R U . . .
C18 C 0.43854(9) 0.9091(4) 0.37567(8) 0.0188(5) Uani 1 1 d . . . . .
C19 C 0.44384(10) 0.8701(4) 0.42250(8) 0.0236(6) Uani 1 1 d . . . . .
H19A H 0.4161 0.9315 0.4367 0.028 Uiso 1 1 calc R U . . .
C20 C 0.48888(10) 0.7430(4) 0.44891(9) 0.0247(6) Uani 1 1 d . . . . .
H20A H 0.4919 0.7205 0.4810 0.030 Uiso 1 1 calc R U . . .
C21 C 0.52954(10) 0.6486(4) 0.42892(8) 0.0203(5) Uani 1 1 d . . . . .
C22 C 0.52445(10) 0.6907(4) 0.38208(8) 0.0217(5) Uani 1 1 d . . . . .
H22A H 0.5522 0.6298 0.3678 0.026 Uiso 1 1 calc R U . . .
C23 C 0.48006(10) 0.8185(4) 0.35582(8) 0.0203(5) Uani 1 1 d . . . . .
H23A H 0.4778 0.8447 0.3240 0.024 Uiso 1 1 calc R U . . .
C24 C 0.57538(10) 0.4963(4) 0.45501(8) 0.0203(5) Uani 1 1 d . . . . .
C25 C 0.61147(11) 0.5464(4) 0.49869(9) 0.0296(6) Uani 1 1 d . . . . .
H25A H 0.6069 0.6801 0.5128 0.036 Uiso 1 1 calc R U . . .
C26 C 0.65421(12) 0.4020(4) 0.52187(9) 0.0353(7) Uani 1 1 d . . . . .
H26A H 0.6784 0.4370 0.5518 0.042 Uiso 1 1 calc R U . . .
C27 C 0.66178(12) 0.2071(4) 0.50154(10) 0.0356(7) Uani 1 1 d . . . . .
H27A H 0.6919 0.1109 0.5170 0.043 Uiso 1 1 calc R U . . .
C28 C 0.62511(11) 0.1541(4) 0.45859(9) 0.0335(7) Uani 1 1 d . . . . .
H28A H 0.6292 0.0192 0.4448 0.040 Uiso 1 1 calc R U . . .
C29 C 0.58248(11) 0.2971(4) 0.43569(9) 0.0280(6) Uani 1 1 d . . . . .
H29A H 0.5575 0.2590 0.4062 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.408(3) . ?
N1 C2 1.408(3) . ?
N1 C1 1.462(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.399(3) . ?
C2 C7 1.404(3) . ?
C3 C4 1.384(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.405(3) . ?
C5 C8 1.513(4) . ?
C6 C7 1.391(3) . ?
C6 H6A 0.9500 . ?
C7 C16 1.532(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.407(3) . ?
C9 C10 1.409(3) . ?
C10 C11 1.376(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.392(3) . ?
C12 C15 1.507(4) . ?
C13 C14 1.388(3) . ?
C13 H13A 0.9500 . ?
C14 C16 1.530(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.536(3) . ?
C16 C18 1.558(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.390(3) . ?
C18 C23 1.393(3) . ?
C19 C20 1.390(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.395(3) . ?
C21 C24 1.493(3) . ?
C22 C23 1.382(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(3) . ?
C24 C29 1.394(3) . ?
C25 C26 1.391(3) . ?
C25 H25A 0.9500 . ?
C26 C27 1.387(4) . ?
C26 H26A 0.9500 . ?
C27 C28 1.382(4) . ?
C27 H27A 0.9500 . ?
C28 C29 1.381(3) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C2 116.65(19) . . ?
C9 N1 C1 118.1(2) . . ?
C2 N1 C1 117.8(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.0(2) . . ?
C3 C2 N1 121.8(2) . . ?
C7 C2 N1 119.2(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 117.4(2) . . ?
C4 C5 C8 121.6(2) . . ?
C6 C5 C8 121.1(3) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 H6A 118.9 . . ?
C5 C6 H6A 118.9 . . ?
C6 C7 C2 119.0(2) . . ?
C6 C7 C16 123.4(2) . . ?
C2 C7 C16 117.6(2) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 N1 118.9(2) . . ?
C14 C9 C10 118.6(2) . . ?
N1 C9 C10 122.6(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
C11 C12 C13 117.2(2) . . ?
C11 C12 C15 121.8(3) . . ?
C13 C12 C15 121.0(3) . . ?
C14 C13 C12 123.0(3) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C9 118.6(2) . . ?
C13 C14 C16 123.5(2) . . ?
C9 C14 C16 117.7(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C7 106.08(18) . . ?
C14 C16 C17 112.81(19) . . ?
C7 C16 C17 112.68(19) . . ?
C14 C16 C18 109.37(18) . . ?
C7 C16 C18 110.32(18) . . ?
C17 C16 C18 105.61(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 118.1(2) . . ?
C19 C18 C16 120.0(2) . . ?
C23 C18 C16 121.7(2) . . ?
C18 C19 C20 121.3(2) . . ?
C18 C19 H19A 119.3 . . ?
C20 C19 H19A 119.3 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 117.7(2) . . ?
C20 C21 C24 122.3(2) . . ?
C22 C21 C24 119.9(2) . . ?
C23 C22 C21 121.7(2) . . ?
C23 C22 H22A 119.1 . . ?
C21 C22 H22A 119.1 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 H23A 119.8 . . ?
C18 C23 H23A 119.8 . . ?
C25 C24 C29 118.4(2) . . ?
C25 C24 C21 121.8(2) . . ?
C29 C24 C21 119.9(2) . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25A 119.8 . . ?
C26 C25 H25A 119.8 . . ?
C27 C26 C25 120.5(2) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C28 C27 C26 119.4(3) . . ?
C28 C27 H27A 120.3 . . ?
C26 C27 H27A 120.3 . . ?
C29 C28 C27 120.1(2) . . ?
C29 C28 H28A 120.0 . . ?
C27 C28 H28A 120.0 . . ?
C28 C29 C24 121.3(2) . . ?
C28 C29 H29A 119.4 . . ?
C24 C29 H29A 119.4 . . ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_JL022_0m
_database_code_depnum_ccdc_archive 'CCDC 1580563'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H29 N'
_chemical_formula_weight         355.50

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'

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

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

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

_cell_length_a                   7.4056(18)
_cell_length_b                   25.093(6)
_cell_length_c                   11.580(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.797(8)
_cell_angle_gamma                90
_cell_volume                     2089.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2557
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      23.30

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18636
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.623
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4787
_reflns_number_gt                2925
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1345P)²+2.5939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4787
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.1025
_refine_ls_wR_factor_ref         0.2932
_refine_ls_wR_factor_gt          0.2596
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.7077(4) 0.15392(11) 0.5575(3) 0.0248(7) Uani 1 1 d . . . . .
C1 C 0.7047(5) 0.21059(14) 0.5285(3) 0.0312(9) Uani 1 1 d . . . . .
H1A H 0.6481 0.2305 0.5836 0.047 Uiso 1 1 calc R U . . .
H1B H 0.6318 0.2161 0.4469 0.047 Uiso 1 1 calc R U . . .
H1C H 0.8321 0.2232 0.5356 0.047 Uiso 1 1 calc R U . . .
C2 C 0.8071(5) 0.13622(13) 0.6681(3) 0.0225(7) Uani 1 1 d . . . . .
C3 C 0.8771(5) 0.17160(14) 0.7611(3) 0.0287(8) Uani 1 1 d . . . . .
H3A H 0.8624 0.2089 0.7477 0.034 Uiso 1 1 calc R U . . .
C4 C 0.9674(6) 0.15310(15) 0.8723(3) 0.0332(9) Uani 1 1 d . . . . .
H4A H 1.0141 0.1781 0.9336 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9920(5) 0.09903(15) 0.8973(3) 0.0309(9) Uani 1 1 d . . . . .
C6 C 0.9241(5) 0.06387(15) 0.8044(3) 0.0295(8) Uani 1 1 d . . . . .
H6A H 0.9403 0.0267 0.8182 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8340(5) 0.08143(14) 0.6927(3) 0.0264(8) Uani 1 1 d . . . . .
H7A H 0.7894 0.0562 0.6314 0.032 Uiso 1 1 calc R U . . .
C8 C 1.0913(8) 0.0796(2) 1.0189(4) 0.0538(13) Uani 1 1 d . . . . .
H8A H 1.1942 0.1038 1.0527 0.081 Uiso 1 1 calc R U . . .
H8B H 1.1402 0.0438 1.0125 0.081 Uiso 1 1 calc R U . . .
H8C H 1.0041 0.0787 1.0706 0.081 Uiso 1 1 calc R U . . .
C9 C 0.6678(5) 0.11786(13) 0.4592(3) 0.0253(8) Uani 1 1 d . . . . .
C10 C 0.8032(5) 0.10750(15) 0.3981(3) 0.0307(8) Uani 1 1 d . . . . .
H10A H 0.9202 0.1249 0.4214 0.037 Uiso 1 1 calc R U . . .
C11 C 0.7707(6) 0.07215(15) 0.3035(3) 0.0330(9) Uani 1 1 d . . . . .
H11A H 0.8657 0.0654 0.2629 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6014(5) 0.04676(14) 0.2678(3) 0.0287(8) Uani 1 1 d . . . . .
C13 C 0.4658(5) 0.05693(14) 0.3289(3) 0.0267(8) Uani 1 1 d . . . . .
H13A H 0.3491 0.0395 0.3044 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4946(5) 0.09227(13) 0.4264(3) 0.0216(7) Uani 1 1 d . . . . .
C15 C 0.5649(7) 0.00905(17) 0.1624(4) 0.0424(11) Uani 1 1 d . . . . .
H15A H 0.6724 -0.0145 0.1684 0.064 Uiso 1 1 calc R U . . .
H15B H 0.5445 0.0297 0.0886 0.064 Uiso 1 1 calc R U . . .
H15C H 0.4543 -0.0124 0.1622 0.064 Uiso 1 1 calc R U . . .
C16 C 0.3449(5) 0.10035(13) 0.4918(3) 0.0235(7) Uani 1 1 d . . . . .
C17 C 0.2579(5) 0.05829(14) 0.5233(3) 0.0297(8) Uani 1 1 d . . . . .
H17A H 0.1393 0.0696 0.5388 0.045 Uiso 1 1 calc R U . . .
H17B H 0.3357 0.0423 0.5954 0.045 Uiso 1 1 calc R U . . .
H17C H 0.2347 0.0320 0.4589 0.045 Uiso 1 1 calc R U . . .
C18 C 0.2934(5) 0.15599(13) 0.5185(3) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.3088(5) 0.17314(14) 0.6362(3) 0.0269(8) Uani 1 1 d . . . . .
C20 C 0.2616(5) 0.22585(16) 0.6561(3) 0.0307(9) Uani 1 1 d . . . . .
H20A H 0.2738 0.2375 0.7356 0.037 Uiso 1 1 calc R U . . .
C21 C 0.1978(5) 0.26164(15) 0.5643(4) 0.0317(9) Uani 1 1 d . . . . .
C22 C 0.1788(5) 0.24359(14) 0.4490(3) 0.0280(8) Uani 1 1 d . . . . .
H22A H 0.1311 0.2672 0.3848 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2271(5) 0.19200(14) 0.4242(3) 0.0255(8) Uani 1 1 d . . . . .
C24 C 0.3711(6) 0.13652(16) 0.7413(3) 0.0325(9) Uani 1 1 d . . . . .
H24A H 0.4159 0.1578 0.8135 0.049 Uiso 1 1 calc R U . . .
H24B H 0.4718 0.1136 0.7285 0.049 Uiso 1 1 calc R U . . .
H24C H 0.2663 0.1144 0.7503 0.049 Uiso 1 1 calc R U . . .
C25 C 0.1441(7) 0.31815(17) 0.5883(4) 0.0483(12) Uani 1 1 d . . . . .
H25A H 0.1649 0.3237 0.6743 0.073 Uiso 1 1 calc R U . . .
H25B H 0.0125 0.3240 0.5503 0.073 Uiso 1 1 calc R U . . .
H25C H 0.2203 0.3434 0.5559 0.073 Uiso 1 1 calc R U . . .
C26 C 0.2027(6) 0.17496(15) 0.2962(3) 0.0314(9) Uani 1 1 d . . . . .
H26A H 0.1157 0.1992 0.2444 0.047 Uiso 1 1 calc R U . . .
H26B H 0.1534 0.1386 0.2863 0.047 Uiso 1 1 calc R U . . .
H26C H 0.3232 0.1761 0.2751 0.047 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 C2 1.389(4) . ?
N1 C9 1.429(4) . ?
N1 C1 1.460(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.396(5) . ?
C2 C7 1.409(5) . ?
C3 C4 1.382(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(5) . ?
C5 C8 1.506(5) . ?
C6 C7 1.379(5) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.383(5) . ?
C9 C14 1.403(5) . ?
C10 C11 1.386(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.379(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.382(5) . ?
C12 C15 1.517(5) . ?
C13 C14 1.411(5) . ?
C13 H13A 0.9500 . ?
C14 C16 1.499(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.332(5) . ?
C16 C18 1.499(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.408(5) . ?
C18 C23 1.412(5) . ?
C19 C20 1.401(5) . ?
C19 C24 1.507(5) . ?
C20 C21 1.385(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.385(5) . ?
C21 C25 1.516(5) . ?
C22 C23 1.391(5) . ?
C22 H22A 0.9500 . ?
C23 C26 1.511(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 119.7(3) . . ?
C2 N1 C1 119.9(3) . . ?
C9 N1 C1 116.4(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.7(3) . . ?
N1 C2 C7 121.1(3) . . ?
C3 C2 C7 117.1(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C6 C5 C4 117.0(3) . . ?
C6 C5 C8 121.6(4) . . ?
C4 C5 C8 121.4(4) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 H7A 119.5 . . ?
C2 C7 H7A 119.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.2(3) . . ?
C10 C9 N1 119.3(3) . . ?
C14 C9 N1 120.5(3) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 C15 120.2(3) . . ?
C13 C12 C15 121.0(4) . . ?
C12 C13 C14 122.4(3) . . ?
C12 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
C9 C14 C13 117.3(3) . . ?
C9 C14 C16 122.7(3) . . ?
C13 C14 C16 120.0(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 119.7(3) . . ?
C17 C16 C18 121.2(3) . . ?
C14 C16 C18 119.0(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 119.1(3) . . ?
C19 C18 C16 121.2(3) . . ?
C23 C18 C16 119.7(3) . . ?
C20 C19 C18 118.8(3) . . ?
C20 C19 C24 118.9(3) . . ?
C18 C19 C24 122.3(3) . . ?
C21 C20 C19 122.6(3) . . ?
C21 C20 H20A 118.7 . . ?
C19 C20 H20A 118.7 . . ?
C22 C21 C20 117.7(3) . . ?
C22 C21 C25 120.8(4) . . ?
C20 C21 C25 121.5(4) . . ?
C21 C22 C23 122.1(3) . . ?
C21 C22 H22A 119.0 . . ?
C23 C22 H22A 119.0 . . ?
C22 C23 C18 119.7(3) . . ?
C22 C23 C26 119.3(3) . . ?
C18 C23 C26 121.0(3) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C2 C3 168.7(3) . . . . ?
C1 N1 C2 C3 11.9(5) . . . . ?
C9 N1 C2 C7 -14.3(5) . . . . ?
C1 N1 C2 C7 -171.1(3) . . . . ?
N1 C2 C3 C4 176.6(3) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 C8 179.8(4) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C8 C5 C6 C7 -179.6(4) . . . . ?
C5 C6 C7 C2 0.1(6) . . . . ?
N1 C2 C7 C6 -176.5(3) . . . . ?
C3 C2 C7 C6 0.6(5) . . . . ?
C2 N1 C9 C10 -80.8(4) . . . . ?
C1 N1 C9 C10 76.8(4) . . . . ?
C2 N1 C9 C14 97.8(4) . . . . ?
C1 N1 C9 C14 -104.6(4) . . . . ?
C14 C9 C10 C11 0.4(5) . . . . ?
N1 C9 C10 C11 179.0(3) . . . . ?
C9 C10 C11 C12 0.4(6) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C10 C11 C12 C15 178.6(4) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C15 C12 C13 C14 -179.2(3) . . . . ?
C10 C9 C14 C13 -1.0(5) . . . . ?
N1 C9 C14 C13 -179.6(3) . . . . ?
C10 C9 C14 C16 177.8(3) . . . . ?
N1 C9 C14 C16 -0.8(5) . . . . ?
C12 C13 C14 C9 0.8(5) . . . . ?
C12 C13 C14 C16 -177.9(3) . . . . ?
C9 C14 C16 C17 -132.2(4) . . . . ?
C13 C14 C16 C17 46.5(5) . . . . ?
C9 C14 C16 C18 48.9(4) . . . . ?
C13 C14 C16 C18 -132.4(3) . . . . ?
C17 C16 C18 C19 60.6(5) . . . . ?
C14 C16 C18 C19 -120.6(4) . . . . ?
C17 C16 C18 C23 -119.0(4) . . . . ?
C14 C16 C18 C23 59.8(4) . . . . ?
C23 C18 C19 C20 -1.4(5) . . . . ?
C16 C18 C19 C20 179.0(3) . . . . ?
C23 C18 C19 C24 177.6(3) . . . . ?
C16 C18 C19 C24 -2.1(5) . . . . ?
C18 C19 C20 C21 0.9(5) . . . . ?
C24 C19 C20 C21 -178.1(3) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C19 C20 C21 C25 178.8(4) . . . . ?
C20 C21 C22 C23 -2.2(5) . . . . ?
C25 C21 C22 C23 179.9(4) . . . . ?
C21 C22 C23 C18 1.7(5) . . . . ?
C21 C22 C23 C26 -180.0(3) . . . . ?
C19 C18 C23 C22 0.1(5) . . . . ?
C16 C18 C23 C22 179.8(3) . . . . ?
C19 C18 C23 C26 -178.2(3) . . . . ?
C16 C18 C23 C26 1.5(5) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_jl018_ortho_a
_database_code_depnum_ccdc_archive 'CCDC 1580562'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 N'
_chemical_formula_weight         327.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

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

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

_cell_length_a                   19.792(5)
_cell_length_b                   12.548(3)
_cell_length_c                   7.5356(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1871.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2492
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      22.16

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16099
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.922
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3871
_reflns_number_gt                2824
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+0.1269P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3871
_refine_ls_number_parameters     232
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.932
_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
N1 N 0.41416(16) 0.6677(3) 0.1552(5) 0.0310(8) Uani 1 1 d . . . . .
C1 C 0.3700(2) 0.6180(4) 0.0272(6) 0.0430(11) Uani 1 1 d . . . . .
H1A H 0.3925 0.6156 -0.0886 0.064 Uiso 1 1 calc R U . . .
H1B H 0.3282 0.6593 0.0175 0.064 Uiso 1 1 calc R U . . .
H1C H 0.3594 0.5453 0.0658 0.064 Uiso 1 1 calc R U . . .
C2 C 0.38563(19) 0.7166(3) 0.3068(5) 0.0274(8) Uani 1 1 d . . . . .
C3 C 0.3177(2) 0.7053(3) 0.3501(6) 0.0338(10) Uani 1 1 d . . . . .
H3A H 0.2892 0.6639 0.2756 0.041 Uiso 1 1 calc R U . . .
C4 C 0.2910(2) 0.7532(3) 0.5000(7) 0.0366(10) Uani 1 1 d . . . . .
H4A H 0.2444 0.7441 0.5269 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3312(2) 0.8146(3) 0.6120(6) 0.0344(10) Uani 1 1 d . . . . .
C6 C 0.3995(2) 0.8247(3) 0.5687(6) 0.0296(9) Uani 1 1 d . . . . .
H6A H 0.4278 0.8655 0.6445 0.036 Uiso 1 1 calc R U . . .
C7 C 0.42796(19) 0.7774(3) 0.4188(5) 0.0245(8) Uani 1 1 d . . . . .
C8 C 0.3023(2) 0.8665(4) 0.7747(7) 0.0476(12) Uani 1 1 d . . . . .
H8A H 0.3316 0.8519 0.8766 0.071 Uiso 1 1 calc R U . . .
H8B H 0.2571 0.8380 0.7977 0.071 Uiso 1 1 calc R U . . .
H8C H 0.2994 0.9437 0.7559 0.071 Uiso 1 1 calc R U . . .
C9 C 0.48205(18) 0.6359(3) 0.1629(5) 0.0255(8) Uani 1 1 d . . . . .
C10 C 0.5061(2) 0.5480(3) 0.0673(5) 0.0314(9) Uani 1 1 d . . . . .
H10A H 0.4760 0.5074 -0.0038 0.038 Uiso 1 1 calc R U . . .
C11 C 0.57366(19) 0.5201(3) 0.0760(5) 0.0304(9) Uani 1 1 d . . . . .
H11A H 0.5893 0.4612 0.0083 0.036 Uiso 1 1 calc R U . . .
C12 C 0.61892(18) 0.5757(3) 0.1803(5) 0.0260(8) Uani 1 1 d . . . . .
C13 C 0.59399(18) 0.6623(3) 0.2778(5) 0.0232(8) Uani 1 1 d . . . . .
H13A H 0.6243 0.7011 0.3512 0.028 Uiso 1 1 calc R U . . .
C14 C 0.52678(18) 0.6937(3) 0.2712(5) 0.0218(8) Uani 1 1 d . . . . .
C15 C 0.69302(19) 0.5475(3) 0.1851(6) 0.0352(10) Uani 1 1 d . . . . .
H15A H 0.6986 0.4714 0.1603 0.053 Uiso 1 1 calc R U . . .
H15B H 0.7114 0.5638 0.3028 0.053 Uiso 1 1 calc R U . . .
H15C H 0.7172 0.5892 0.0952 0.053 Uiso 1 1 calc R U . . .
C16 C 0.50129(18) 0.7949(3) 0.3637(5) 0.0240(8) Uani 1 1 d . . . . .
C17 C 0.5008(2) 0.8856(3) 0.2233(5) 0.0307(9) Uani 1 1 d . . . . .
H17A H 0.4851 0.9518 0.2786 0.046 Uiso 1 1 calc R U . . .
H17B H 0.4703 0.8663 0.1259 0.046 Uiso 1 1 calc R U . . .
H17C H 0.5465 0.8959 0.1769 0.046 Uiso 1 1 calc R U . . .
C18 C 0.54632(17) 0.8204(3) 0.5211(5) 0.0234(8) Uani 1 1 d . . . . .
C19 C 0.5484(2) 0.7512(3) 0.6666(6) 0.0295(8) Uani 1 1 d . . . . .
H19A H 0.5200 0.6901 0.6670 0.035 Uiso 1 1 calc R U . . .
C20 C 0.59028(19) 0.7690(3) 0.8088(5) 0.0312(9) Uani 1 1 d . . . . .
H20A H 0.5903 0.7200 0.9049 0.037 Uiso 1 1 calc R U . . .
C21 C 0.63293(17) 0.8577(3) 0.8148(5) 0.0286(9) Uani 1 1 d . . . . .
C22 C 0.63163(18) 0.9263(3) 0.6702(6) 0.0310(9) Uani 1 1 d . . . . .
H22A H 0.6604 0.9868 0.6694 0.037 Uiso 1 1 calc R U . . .
C23 C 0.58907(17) 0.9081(3) 0.5266(6) 0.0262(8) Uani 1 1 d . . . . .
H23A H 0.5892 0.9568 0.4300 0.031 Uiso 1 1 calc R U . . .
C24 C 0.6783(2) 0.8774(4) 0.9709(6) 0.0420(11) Uani 1 1 d . . . . .
H24A H 0.7187 0.9159 0.9316 0.063 Uiso 1 1 calc R U . . .
H24B H 0.6915 0.8091 1.0235 0.063 Uiso 1 1 calc R U . . .
H24C H 0.6542 0.9202 1.0594 0.063 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 C9 1.403(5) . ?
N1 C2 1.415(5) . ?
N1 C1 1.443(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.391(5) . ?
C2 C7 1.413(5) . ?
C3 C4 1.385(6) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(5) . ?
C5 C8 1.502(6) . ?
C6 C7 1.395(5) . ?
C6 H6A 0.9500 . ?
C7 C16 1.526(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.401(5) . ?
C9 C14 1.406(5) . ?
C10 C11 1.383(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.381(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.402(5) . ?
C12 C15 1.509(5) . ?
C13 C14 1.388(5) . ?
C13 H13A 0.9500 . ?
C14 C16 1.534(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.518(5) . ?
C16 C17 1.553(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.389(5) . ?
C18 C19 1.399(6) . ?
C19 C20 1.373(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.398(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.389(6) . ?
C21 C24 1.500(6) . ?
C22 C23 1.390(6) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C2 118.2(3) . . ?
C9 N1 C1 119.0(3) . . ?
C2 N1 C1 119.1(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.2(4) . . ?
C3 C2 N1 122.1(3) . . ?
C7 C2 N1 118.7(3) . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 117.5(4) . . ?
C4 C5 C8 121.2(4) . . ?
C6 C5 C8 121.3(4) . . ?
C7 C6 C5 122.8(4) . . ?
C7 C6 H6A 118.6 . . ?
C5 C6 H6A 118.6 . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C16 122.9(3) . . ?
C2 C7 C16 118.6(3) . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 121.9(3) . . ?
C10 C9 C14 119.4(3) . . ?
N1 C9 C14 118.7(3) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C11 C12 C13 117.5(3) . . ?
C11 C12 C15 121.8(4) . . ?
C13 C12 C15 120.7(3) . . ?
C14 C13 C12 122.6(3) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C9 118.5(3) . . ?
C13 C14 C16 122.3(3) . . ?
C9 C14 C16 118.9(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C16 C7 112.1(3) . . ?
C18 C16 C14 109.7(3) . . ?
C7 C16 C14 108.5(3) . . ?
C18 C16 C17 112.4(3) . . ?
C7 C16 C17 106.5(3) . . ?
C14 C16 C17 107.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 116.8(3) . . ?
C23 C18 C16 123.2(3) . . ?
C19 C18 C16 119.9(3) . . ?
C20 C19 C18 121.8(4) . . ?
C20 C19 H19A 119.1 . . ?
C18 C19 H19A 119.1 . . ?
C19 C20 C21 121.3(4) . . ?
C19 C20 H20A 119.3 . . ?
C21 C20 H20A 119.3 . . ?
C22 C21 C20 117.2(4) . . ?
C22 C21 C24 121.6(4) . . ?
C20 C21 C24 121.2(4) . . ?
C21 C22 C23 121.4(3) . . ?
C21 C22 H22A 119.3 . . ?
C23 C22 H22A 119.3 . . ?
C18 C23 C22 121.5(4) . . ?
C18 C23 H23A 119.3 . . ?
C22 C23 H23A 119.3 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.058

