# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_dm17379
_database_code_depnum_ccdc_archive 'CCDC 1569798'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.3887(13)
_cell_length_b                   9.1859(8)
_cell_length_c                   24.515(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3240.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5370
_cell_measurement_theta_min      5.517
_cell_measurement_theta_max      48.323

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            21314
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3008
_reflns_number_gt                2291
_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-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)+(0.0486P)²+0.7827P] 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       0.0115(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.51430(8) 1.16339(13) 0.57412(5) 0.0388(3) Uani 1 1 d . . . . .
O1 O 0.62233(8) 1.22707(13) 0.63778(5) 0.0555(3) Uani 1 1 d . . . . .
C1 C 0.34846(12) 0.8450(2) 0.73440(8) 0.0583(5) Uani 1 1 d . . . . .
H1A H 0.3703 0.8177 0.7704 0.070 Uiso 1 1 calc R U . . .
H1B H 0.3300 0.7643 0.7113 0.070 Uiso 1 1 calc R U . . .
C2 C 0.29519(12) 0.9857(2) 0.72907(7) 0.0554(5) Uani 1 1 d . . . . .
H2A H 0.2450 0.9895 0.7027 0.067 Uiso 1 1 calc R U . . .
H2B H 0.2853 1.0430 0.7618 0.067 Uiso 1 1 calc R U . . .
C3 C 0.39270(11) 0.97290(18) 0.70776(6) 0.0435(4) Uani 1 1 d . . . . .
C4 C 0.47570(11) 1.0684(2) 0.72577(6) 0.0491(4) Uani 1 1 d . . . . .
H4A H 0.5320 1.0144 0.7337 0.059 Uiso 1 1 calc R U . . .
H4B H 0.4613 1.1373 0.7545 0.059 Uiso 1 1 calc R U . . .
C5 C 0.47169(10) 1.13332(16) 0.66710(6) 0.0390(4) Uani 1 1 d . . . . .
C6 C 0.42545(10) 0.99032(15) 0.64767(6) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.37276(10) 1.02409(15) 0.59645(6) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.28494(11) 0.97666(18) 0.58169(7) 0.0465(4) Uani 1 1 d . . . . .
H8 H 0.2512 0.9190 0.6058 0.056 Uiso 1 1 calc R U . . .
C9 C 0.24645(12) 1.01343(19) 0.53178(7) 0.0542(4) Uani 1 1 d . . . . .
H9 H 0.1873 0.9812 0.5225 0.065 Uiso 1 1 calc R U . . .
C10 C 0.29663(12) 1.0980(2) 0.49620(7) 0.0530(4) Uani 1 1 d . . . . .
H10 H 0.2712 1.1222 0.4625 0.064 Uiso 1 1 calc R U . . .
C11 C 0.38428(11) 1.14765(17) 0.50963(6) 0.0453(4) Uani 1 1 d . . . . .
H11 H 0.4173 1.2048 0.4850 0.054 Uiso 1 1 calc R U . . .
C12 C 0.42352(10) 1.11242(15) 0.55988(6) 0.0362(3) Uani 1 1 d . . . . .
C13 C 0.54576(10) 1.17754(16) 0.62728(6) 0.0398(4) Uani 1 1 d . . . . .
C14 C 0.57392(12) 1.22253(19) 0.53114(7) 0.0521(4) Uani 1 1 d . . . . .
H14A H 0.5542 1.3196 0.5223 0.078 Uiso 1 1 calc R U . . .
H14B H 0.5695 1.1622 0.4993 0.078 Uiso 1 1 calc R U . . .
H14C H 0.6371 1.2246 0.5436 0.078 Uiso 1 1 calc R U . . .
C15 C 0.40480(11) 1.26481(17) 0.66965(7) 0.0508(4) Uani 1 1 d . . . . .
H15A H 0.4358 1.3457 0.6865 0.076 Uiso 1 1 calc R U . . .
H15B H 0.3509 1.2392 0.6906 0.076 Uiso 1 1 calc R U . . .
H15C H 0.3862 1.2912 0.6334 0.076 Uiso 1 1 calc R U . . .
C16 C 0.49234(10) 0.86218(15) 0.63600(6) 0.0389(3) Uani 1 1 d . . . . .
C17 C 0.45370(12) 0.73346(17) 0.61628(7) 0.0485(4) Uani 1 1 d . . . . .
H17 H 0.3905 0.7302 0.6085 0.058 Uiso 1 1 calc R U . . .
C18 C 0.50731(15) 0.61026(19) 0.60796(8) 0.0613(5) Uani 1 1 d . . . . .
H18 H 0.4797 0.5256 0.5949 0.074 Uiso 1 1 calc R U . . .
C19 C 0.60092(15) 0.6120(2) 0.61887(8) 0.0659(6) Uani 1 1 d . . . . .
H19 H 0.6367 0.5290 0.6135 0.079 Uiso 1 1 calc R U . . .
C20 C 0.64107(13) 0.7380(2) 0.63788(8) 0.0609(5) Uani 1 1 d . . . . .
H20 H 0.7045 0.7402 0.6451 0.073 Uiso 1 1 calc R U . . .
C21 C 0.58755(11) 0.86241(18) 0.64641(7) 0.0491(4) Uani 1 1 d . . . . .
H21 H 0.6158 0.9468 0.6592 0.059 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 C13 1.3857(19) . ?
N1 C12 1.4309(18) . ?
N1 C14 1.4632(19) . ?
O1 C13 1.2194(18) . ?
C1 C3 1.487(2) . ?
C1 C2 1.508(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.546(2) . ?
C3 C6 1.555(2) . ?
C4 C5 1.558(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C13 1.501(2) . ?
C5 C15 1.546(2) . ?
C5 C6 1.548(2) . ?
C6 C7 1.499(2) . ?
C6 C16 1.547(2) . ?
C7 C8 1.385(2) . ?
C7 C12 1.413(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(2) . ?
C11 H11 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.393(2) . ?
C16 C21 1.394(2) . ?
C17 C18 1.385(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C12 123.94(12) . . ?
C13 N1 C14 116.80(13) . . ?
C12 N1 C14 118.75(13) . . ?
C3 C1 C2 60.18(11) . . ?
C3 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C3 C1 H1B 117.8 . . ?
C2 C1 H1B 117.8 . . ?
H1A C1 H1B 114.9 . . ?
C3 C2 C1 59.21(11) . . ?
C3 C2 H2A 117.9 . . ?
C1 C2 H2A 117.9 . . ?
C3 C2 H2B 117.9 . . ?
C1 C2 H2B 117.9 . . ?
H2A C2 H2B 115.0 . . ?
C1 C3 C2 60.61(11) . . ?
C1 C3 C4 130.80(14) . . ?
C2 C3 C4 125.30(15) . . ?
C1 C3 C6 128.84(15) . . ?
C2 C3 C6 127.20(14) . . ?
C4 C3 C6 88.74(11) . . ?
C3 C4 C5 85.71(11) . . ?
C3 C4 H4A 114.4 . . ?
C5 C4 H4A 114.4 . . ?
C3 C4 H4B 114.4 . . ?
C5 C4 H4B 114.4 . . ?
H4A C4 H4B 111.5 . . ?
C13 C5 C15 104.89(12) . . ?
C13 C5 C6 109.56(12) . . ?
C15 C5 C6 114.08(12) . . ?
C13 C5 C4 132.65(13) . . ?
C15 C5 C4 106.56(13) . . ?
C6 C5 C4 88.57(11) . . ?
C7 C6 C16 108.49(12) . . ?
C7 C6 C5 107.43(11) . . ?
C16 C6 C5 115.80(12) . . ?
C7 C6 C3 131.42(13) . . ?
C16 C6 C3 106.59(11) . . ?
C5 C6 C3 85.76(11) . . ?
C8 C7 C12 119.12(14) . . ?
C8 C7 C6 127.96(13) . . ?
C12 C7 C6 112.89(12) . . ?
C7 C8 C9 121.27(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.27(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.03(16) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 120.29(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.02(14) . . ?
C11 C12 N1 120.64(13) . . ?
C7 C12 N1 120.34(13) . . ?
O1 C13 N1 121.92(14) . . ?
O1 C13 C5 127.23(14) . . ?
N1 C13 C5 110.75(12) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.20(15) . . ?
C17 C16 C6 117.49(13) . . ?
C21 C16 C6 125.21(14) . . ?
C18 C17 C16 121.49(17) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 120.54(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.21(17) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.59(18) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.96(17) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?

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
C2 C1 C3 C4 113.0(2) . . . . ?
C2 C1 C3 C6 -115.94(19) . . . . ?
C1 C2 C3 C4 -121.34(18) . . . . ?
C1 C2 C3 C6 118.44(19) . . . . ?
C1 C3 C4 C5 168.95(18) . . . . ?
C2 C3 C4 C5 -111.60(16) . . . . ?
C6 C3 C4 C5 24.89(11) . . . . ?
C3 C4 C5 C13 -140.62(16) . . . . ?
C3 C4 C5 C15 89.71(13) . . . . ?
C3 C4 C5 C6 -25.02(11) . . . . ?
C13 C5 C6 C7 -67.65(15) . . . . ?
C15 C5 C6 C7 49.57(16) . . . . ?
C4 C5 C6 C7 157.09(12) . . . . ?
C13 C5 C6 C16 53.74(16) . . . . ?
C15 C5 C6 C16 170.96(12) . . . . ?
C4 C5 C6 C16 -81.52(13) . . . . ?
C13 C5 C6 C3 160.13(12) . . . . ?
C15 C5 C6 C3 -82.66(14) . . . . ?
C4 C5 C6 C3 24.86(11) . . . . ?
C1 C3 C6 C7 80.1(2) . . . . ?
C2 C3 C6 C7 0.5(3) . . . . ?
C4 C3 C6 C7 -134.65(16) . . . . ?
C1 C3 C6 C16 -54.6(2) . . . . ?
C2 C3 C6 C16 -134.25(16) . . . . ?
C4 C3 C6 C16 90.60(13) . . . . ?
C1 C3 C6 C5 -170.28(17) . . . . ?
C2 C3 C6 C5 110.07(17) . . . . ?
C4 C3 C6 C5 -25.07(11) . . . . ?
C16 C6 C7 C8 96.52(18) . . . . ?
C5 C6 C7 C8 -137.61(16) . . . . ?
C3 C6 C7 C8 -37.6(2) . . . . ?
C16 C6 C7 C12 -81.75(14) . . . . ?
C5 C6 C7 C12 44.12(16) . . . . ?
C3 C6 C7 C12 144.12(15) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C9 -177.77(15) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C10 C11 C12 N1 179.99(14) . . . . ?
C8 C7 C12 C11 -0.9(2) . . . . ?
C6 C7 C12 C11 177.54(13) . . . . ?
C8 C7 C12 N1 179.81(13) . . . . ?
C6 C7 C12 N1 -1.76(19) . . . . ?
C13 N1 C12 C11 157.12(14) . . . . ?
C14 N1 C12 C11 -14.4(2) . . . . ?
C13 N1 C12 C7 -23.6(2) . . . . ?
C14 N1 C12 C7 164.86(14) . . . . ?
C12 N1 C13 O1 -176.93(14) . . . . ?
C14 N1 C13 O1 -5.2(2) . . . . ?
C12 N1 C13 C5 -0.39(19) . . . . ?
C14 N1 C13 C5 171.30(13) . . . . ?
C15 C5 C13 O1 98.00(18) . . . . ?
C6 C5 C13 O1 -139.16(16) . . . . ?
C4 C5 C13 O1 -32.2(3) . . . . ?
C15 C5 C13 N1 -78.31(15) . . . . ?
C6 C5 C13 N1 44.54(16) . . . . ?
C4 C5 C13 N1 151.47(16) . . . . ?
C7 C6 C16 C17 -56.60(16) . . . . ?
C5 C6 C16 C17 -177.42(13) . . . . ?
C3 C6 C16 C17 89.23(16) . . . . ?
C7 C6 C16 C21 127.09(15) . . . . ?
C5 C6 C16 C21 6.3(2) . . . . ?
C3 C6 C16 C21 -87.08(17) . . . . ?
C21 C16 C17 C18 0.8(2) . . . . ?
C6 C16 C17 C18 -175.86(14) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 -0.7(2) . . . . ?
C6 C16 C21 C20 175.63(15) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.029

_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_d8v17452_0m
_database_code_depnum_ccdc_archive 'CCDC 1579802'
_audit_update_record             
;
2017-10-13 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4746(4)
_cell_length_b                   9.4905(4)
_cell_length_c                   9.7931(4)
_cell_angle_alpha                78.0810(10)
_cell_angle_beta                 70.1660(10)
_cell_angle_gamma                77.5270(10)
_cell_volume                     800.24(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      4.629
_cell_measurement_theta_max      54.952

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            15745
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.454
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2954
_reflns_number_gt                2548
_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-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)+(0.0414P)²+0.2819P] 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       0.25(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2954
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.18861(14) 0.48372(13) 0.19361(14) 0.0378(3) Uani 1 1 d . . . . .
O1 O 0.19558(17) 0.41857(16) -0.01691(15) 0.0697(4) Uani 1 1 d . . . . .
C1 C 0.24430(18) 0.39556(17) 0.08740(17) 0.0400(4) Uani 1 1 d . . . . .
C2 C 0.37001(16) 0.26820(15) 0.09623(15) 0.0325(3) Uani 1 1 d . . . . .
C3 C 0.30386(18) 0.12449(17) 0.12696(17) 0.0407(4) Uani 1 1 d . . . . .
H3A H 0.2084 0.1369 0.1064 0.049 Uiso 1 1 calc R U . . .
H3B H 0.3757 0.0452 0.0813 0.049 Uiso 1 1 calc R U . . .
C4 C 0.28612(16) 0.11650(15) 0.28782(16) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.13642(18) 0.12526(19) 0.40614(19) 0.0471(4) Uani 1 1 d . . . . .
H5A H 0.0482 0.1155 0.3819 0.056 Uiso 1 1 calc R U . . .
H5B H 0.1165 0.1915 0.4762 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2557(2) -0.00675(18) 0.41055(19) 0.0490(4) Uani 1 1 d . . . . .
H6A H 0.3077 -0.0201 0.4833 0.059 Uiso 1 1 calc R U . . .
H6B H 0.2394 -0.0962 0.3891 0.059 Uiso 1 1 calc R U . . .
C7 C 0.39859(15) 0.22565(14) 0.25112(15) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.34587(15) 0.34514(15) 0.34563(15) 0.0304(3) Uani 1 1 d . . . . .
C9 C 0.38748(18) 0.33088(18) 0.47121(17) 0.0398(4) Uani 1 1 d . . . . .
H9 H 0.4536 0.2484 0.4938 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3335(2) 0.4358(2) 0.56391(19) 0.0502(4) Uani 1 1 d . . . . .
H10 H 0.3608 0.4230 0.6489 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2393(2) 0.5587(2) 0.5284(2) 0.0553(5) Uani 1 1 d . . . . .
H11 H 0.2052 0.6316 0.5880 0.066 Uiso 1 1 calc R U . . .
C12 C 0.1945(2) 0.57563(18) 0.40562(19) 0.0479(4) Uani 1 1 d . . . . .
H12 H 0.1304 0.6598 0.3830 0.057 Uiso 1 1 calc R U . . .
C13 C 0.24415(16) 0.46797(15) 0.31449(16) 0.0331(3) Uani 1 1 d . . . . .
C14 C 0.0662(2) 0.6042(2) 0.1780(2) 0.0561(5) Uani 1 1 d . . . . .
H14A H 0.1057 0.6945 0.1479 0.084 Uiso 1 1 calc R U . . .
H14B H -0.0128 0.6075 0.2704 0.084 Uiso 1 1 calc R U . . .
H14C H 0.0256 0.5893 0.1056 0.084 Uiso 1 1 calc R U . . .
C15 C 0.50419(18) 0.28940(18) -0.04187(16) 0.0423(4) Uani 1 1 d . . . . .
H15A H 0.4716 0.3002 -0.1267 0.064 Uiso 1 1 calc R U . . .
H15B H 0.5825 0.2061 -0.0427 0.064 Uiso 1 1 calc R U . . .
H15C H 0.5430 0.3753 -0.0433 0.064 Uiso 1 1 calc R U . . .
C16 C 0.56327(16) 0.15470(15) 0.23392(15) 0.0319(3) Uani 1 1 d . . . . .
C17 C 0.61115(18) 0.00566(16) 0.23374(17) 0.0392(4) Uani 1 1 d . . . . .
H17 H 0.5399 -0.0552 0.2520 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7637(2) -0.05400(19) 0.20678(19) 0.0496(4) Uani 1 1 d . . . . .
H18 H 0.7935 -0.1540 0.2066 0.059 Uiso 1 1 calc R U . . .
C19 C 0.87093(19) 0.0336(2) 0.18037(19) 0.0515(5) Uani 1 1 d . . . . .
H19 H 0.9730 -0.0067 0.1628 0.062 Uiso 1 1 calc R U . . .
C20 C 0.82581(18) 0.1817(2) 0.18022(18) 0.0471(4) Uani 1 1 d . . . . .
H20 H 0.8978 0.2416 0.1625 0.056 Uiso 1 1 calc R U . . .
C21 C 0.67402(17) 0.24181(17) 0.20631(17) 0.0387(4) Uani 1 1 d . . . . .
H21 H 0.6453 0.3420 0.2054 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 C1 1.363(2) . ?
N1 C13 1.4200(19) . ?
N1 C14 1.4662(19) . ?
O1 C1 1.2201(19) . ?
C1 C2 1.514(2) . ?
C2 C15 1.522(2) . ?
C2 C3 1.554(2) . ?
C2 C7 1.5860(19) . ?
C3 C4 1.514(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.492(2) . ?
C4 C5 1.495(2) . ?
C4 C7 1.5494(19) . ?
C5 C6 1.499(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.5058(19) . ?
C7 C16 1.5268(19) . ?
C8 C9 1.387(2) . ?
C8 C13 1.396(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.395(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.389(2) . ?
C16 C21 1.395(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 124.18(12) . . ?
C1 N1 C14 117.00(13) . . ?
C13 N1 C14 118.81(13) . . ?
O1 C1 N1 120.92(14) . . ?
O1 C1 C2 118.91(14) . . ?
N1 C1 C2 120.17(13) . . ?
C1 C2 C15 107.84(12) . . ?
C1 C2 C3 108.45(12) . . ?
C15 C2 C3 116.87(12) . . ?
C1 C2 C7 114.67(11) . . ?
C15 C2 C7 119.31(12) . . ?
C3 C2 C7 88.49(10) . . ?
C4 C3 C2 88.59(10) . . ?
C4 C3 H3A 113.9 . . ?
C2 C3 H3A 113.9 . . ?
C4 C3 H3B 113.9 . . ?
C2 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?
C6 C4 C5 60.27(11) . . ?
C6 C4 C3 130.13(13) . . ?
C5 C4 C3 123.90(13) . . ?
C6 C4 C7 129.51(13) . . ?
C5 C4 C7 124.33(12) . . ?
C3 C4 C7 91.31(11) . . ?
C4 C5 C6 59.76(10) . . ?
C4 C5 H5A 117.8 . . ?
C6 C5 H5A 117.8 . . ?
C4 C5 H5B 117.8 . . ?
C6 C5 H5B 117.8 . . ?
H5A C5 H5B 114.9 . . ?
C4 C6 C5 59.97(10) . . ?
C4 C6 H6A 117.8 . . ?
C5 C6 H6A 117.8 . . ?
C4 C6 H6B 117.8 . . ?
C5 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?
C8 C7 C16 112.87(11) . . ?
C8 C7 C4 114.52(11) . . ?
C16 C7 C4 114.54(11) . . ?
C8 C7 C2 115.46(11) . . ?
C16 C7 C2 110.65(11) . . ?
C4 C7 C2 86.21(10) . . ?
C9 C8 C13 118.50(13) . . ?
C9 C8 C7 121.04(13) . . ?
C13 C8 C7 120.28(12) . . ?
C10 C9 C8 121.94(15) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C11 C10 C9 118.85(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.69(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.76(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.14(14) . . ?
C12 C13 N1 119.67(14) . . ?
C8 C13 N1 121.18(12) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 117.53(14) . . ?
C17 C16 C7 122.53(13) . . ?
C21 C16 C7 119.77(12) . . ?
C16 C17 C18 121.07(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.49(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.36(15) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.38(16) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 121.17(15) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?

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
C13 N1 C1 O1 -177.01(15) . . . . ?
C14 N1 C1 O1 1.4(2) . . . . ?
C13 N1 C1 C2 2.1(2) . . . . ?
C14 N1 C1 C2 -179.58(14) . . . . ?
O1 C1 C2 C15 57.95(19) . . . . ?
N1 C1 C2 C15 -121.14(15) . . . . ?
O1 C1 C2 C3 -69.48(19) . . . . ?
N1 C1 C2 C3 111.43(15) . . . . ?
O1 C1 C2 C7 -166.52(15) . . . . ?
N1 C1 C2 C7 14.4(2) . . . . ?
C1 C2 C3 C4 -98.12(12) . . . . ?
C15 C2 C3 C4 139.81(13) . . . . ?
C7 C2 C3 C4 17.43(10) . . . . ?
C2 C3 C4 C6 -166.25(16) . . . . ?
C2 C3 C4 C5 116.17(15) . . . . ?
C2 C3 C4 C7 -17.86(11) . . . . ?
C3 C4 C5 C6 120.70(17) . . . . ?
C7 C4 C5 C6 -119.81(17) . . . . ?
C3 C4 C6 C5 -111.01(18) . . . . ?
C7 C4 C6 C5 111.76(17) . . . . ?
C6 C4 C7 C8 -77.46(19) . . . . ?
C5 C4 C7 C8 0.1(2) . . . . ?
C3 C4 C7 C8 133.83(12) . . . . ?
C6 C4 C7 C16 55.2(2) . . . . ?
C5 C4 C7 C16 132.80(15) . . . . ?
C3 C4 C7 C16 -93.48(13) . . . . ?
C6 C4 C7 C2 166.23(16) . . . . ?
C5 C4 C7 C2 -116.21(15) . . . . ?
C3 C4 C7 C2 17.52(11) . . . . ?
C1 C2 C7 C8 -22.82(17) . . . . ?
C15 C2 C7 C8 107.30(15) . . . . ?
C3 C2 C7 C8 -132.47(12) . . . . ?
C1 C2 C7 C16 -152.58(12) . . . . ?
C15 C2 C7 C16 -22.46(17) . . . . ?
C3 C2 C7 C16 97.78(12) . . . . ?
C1 C2 C7 C4 92.59(13) . . . . ?
C15 C2 C7 C4 -137.29(13) . . . . ?
C3 C2 C7 C4 -17.05(10) . . . . ?
C16 C7 C8 C9 -39.89(18) . . . . ?
C4 C7 C8 C9 93.59(16) . . . . ?
C2 C7 C8 C9 -168.55(13) . . . . ?
C16 C7 C8 C13 145.13(13) . . . . ?
C4 C7 C8 C13 -81.39(16) . . . . ?
C2 C7 C8 C13 16.47(18) . . . . ?
C13 C8 C9 C10 -1.3(2) . . . . ?
C7 C8 C9 C10 -176.37(14) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C9 C10 C11 C12 2.3(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C8 -2.9(2) . . . . ?
C11 C12 C13 N1 175.97(15) . . . . ?
C9 C8 C13 C12 3.5(2) . . . . ?
C7 C8 C13 C12 178.62(13) . . . . ?
C9 C8 C13 N1 -175.37(13) . . . . ?
C7 C8 C13 N1 -0.3(2) . . . . ?
C1 N1 C13 C12 170.94(15) . . . . ?
C14 N1 C13 C12 -7.4(2) . . . . ?
C1 N1 C13 C8 -10.2(2) . . . . ?
C14 N1 C13 C8 171.48(14) . . . . ?
C8 C7 C16 C17 140.81(14) . . . . ?
C4 C7 C16 C17 7.35(19) . . . . ?
C2 C7 C16 C17 -88.07(16) . . . . ?
C8 C7 C16 C21 -44.11(17) . . . . ?
C4 C7 C16 C21 -177.58(12) . . . . ?
C2 C7 C16 C21 87.00(15) . . . . ?
C21 C16 C17 C18 -0.1(2) . . . . ?
C7 C16 C17 C18 175.07(14) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 0.3(2) . . . . ?
C17 C16 C21 C20 -0.2(2) . . . . ?
C7 C16 C21 C20 -175.53(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14C O1 0.96 2.55 3.423(2) 152.0 2_565
C14 H14C O1 0.96 2.55 3.423(2) 152.0 2_565
C14 H14C O1 0.96 2.55 3.423(2) 152.0 2_565

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

