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

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

data_cd1394a
_database_code_depnum_ccdc_archive 'CCDC 1457713'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date             2015-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N'
_chemical_formula_sum            'C24 H23 N'
_chemical_formula_weight         325.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.9502(6)
_cell_length_b                   9.1881(5)
_cell_length_c                   11.6731(8)
_cell_angle_alpha                83.963(6)
_cell_angle_beta                 70.783(5)
_cell_angle_gamma                77.642(5)
_cell_volume                     884.82(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5885
_cell_measurement_temperature    98
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6971
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 180
	           Slice: -80.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 122
	           Slice: -50.0000 - 11.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 84
	           Slice: -53.0000 - -11.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 35.0000
	          2theta: -35.0000
scan:
	Number of images: 50
	           Slice: -35.0000 - -10.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.0000
	          2theta: -35.0000
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.023966
_diffrn_orient_matrix_UB_12      0.053113
_diffrn_orient_matrix_UB_13      0.105065
_diffrn_orient_matrix_UB_21      0.109822
_diffrn_orient_matrix_UB_22      -0.009171
_diffrn_orient_matrix_UB_23      0.005477
_diffrn_orient_matrix_UB_31      0.004983
_diffrn_orient_matrix_UB_32      0.063749
_diffrn_orient_matrix_UB_33      -0.063792
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3573
_reflns_number_total             4038
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.2930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C11(H11), C19(H19), C5(H5), C14(H14), C23(H23), C6(H6),
 C20(H20), C12(H12), C22(H22), C21(H21), C13(H13)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.53300(11) 0.60607(10) 0.59911(8) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.55606(12) 0.44664(11) 0.75620(9) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.39311(12) 0.53077(11) 0.78689(9) 0.0174(2) Uani 1 1 d . . . . .
C10 C 0.65456(12) 0.81456(11) 0.47596(9) 0.0171(2) Uani 1 1 d . . . . .
C18 C 0.09940(12) 0.61932(12) 0.88935(9) 0.0183(2) Uani 1 1 d . . . . .
C1 C 0.38672(13) 0.62485(12) 0.68913(10) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.2954 0.6926 0.6842 0.022 Uiso 1 1 calc R . . . .
C8 C 0.63935(13) 0.49787(11) 0.63816(10) 0.0180(2) Uani 1 1 d . . . . .
C7 C 0.80100(13) 0.43995(12) 0.57728(10) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.8533 0.4754 0.5000 0.025 Uiso 1 1 calc R . . . .
C11 C 0.68079(13) 0.85773(12) 0.57703(10) 0.0210(2) Uani 1 1 d . . . . .
H11 H 0.6421 0.8097 0.6520 0.025 Uiso 1 1 calc R . . . .
C4 C 0.63898(13) 0.33102(12) 0.81492(10) 0.0195(2) Uani 1 1 d . . . . .
C15 C 0.70923(13) 0.88978(12) 0.36382(10) 0.0200(2) Uani 1 1 d . . . . .
C19 C 0.01514(13) 0.57620(13) 0.82145(10) 0.0232(2) Uani 1 1 d . . . . .
H19 H 0.0510 0.4836 0.7863 0.028 Uiso 1 1 calc R . . . .
C9 C 0.56766(13) 0.68817(12) 0.48344(9) 0.0192(2) Uani 1 1 d . . . . .
H9A H 0.4669 0.7284 0.4671 0.023 Uiso 1 1 calc R . . . .
H9B H 0.6327 0.6193 0.4203 0.023 Uiso 1 1 calc R . . . .
C17 C 0.25251(12) 0.52070(12) 0.90063(9) 0.0185(2) Uani 1 1 d . . . . .
H17A H 0.2373 0.4182 0.9159 0.022 Uiso 1 1 calc R . . . .
H17B H 0.2761 0.5503 0.9692 0.022 Uiso 1 1 calc R . . . .
C5 C 0.79930(13) 0.27481(12) 0.75356(11) 0.0227(2) Uani 1 1 d . . . . .
H5 H 0.8560 0.1990 0.7911 0.027 Uiso 1 1 calc R . . . .
C14 C 0.79510(14) 1.00185(12) 0.35555(11) 0.0243(2) Uani 1 1 d . . . . .
H14 H 0.8346 1.0501 0.2809 0.029 Uiso 1 1 calc R . . . .
C24 C 0.55572(14) 0.26657(13) 0.93840(10) 0.0229(2) Uani 1 1 d . . . . .
H24A H 0.5080 0.3452 0.9949 0.034 Uiso 1 1 calc GR . . . .
H24B H 0.6331 0.1951 0.9660 0.034 Uiso 1 1 calc GR . . . .
H24C H 0.4732 0.2185 0.9328 0.034 Uiso 1 1 calc GR . . . .
C23 C 0.04177(14) 0.75736(12) 0.94210(10) 0.0229(2) Uani 1 1 d . . . . .
H23 H 0.0952 0.7876 0.9889 0.028 Uiso 1 1 calc R . . . .
C6 C 0.87944(13) 0.32792(12) 0.63691(11) 0.0231(2) Uani 1 1 d . . . . .
H6 H 0.9871 0.2868 0.5993 0.028 Uiso 1 1 calc R . . . .
C20 C -0.12099(14) 0.66879(15) 0.80542(11) 0.0287(3) Uani 1 1 d . . . . .
H20 H -0.1759 0.6382 0.7599 0.034 Uiso 1 1 calc R . . . .
C12 C 0.76424(15) 0.97198(13) 0.56742(11) 0.0267(3) Uani 1 1 d . . . . .
H12 H 0.7806 1.0006 0.6358 0.032 Uiso 1 1 calc R . . . .
C22 C -0.09461(15) 0.85095(13) 0.92599(11) 0.0276(3) Uani 1 1 d . . . . .
H22 H -0.1314 0.9432 0.9616 0.033 Uiso 1 1 calc R . . . .
C21 C -0.17566(14) 0.80742(14) 0.85727(11) 0.0296(3) Uani 1 1 d . . . . .
H21 H -0.2662 0.8705 0.8458 0.036 Uiso 1 1 calc R . . . .
C13 C 0.82296(14) 1.04302(13) 0.45612(12) 0.0271(3) Uani 1 1 d . . . . .
H13 H 0.8809 1.1181 0.4489 0.032 Uiso 1 1 calc R . . . .
C16 C 0.67514(17) 0.85199(14) 0.25384(10) 0.0305(3) Uani 1 1 d . . . . .
H16A H 0.7361 0.7551 0.2279 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.7054 0.9249 0.1897 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.5622 0.8518 0.2738 0.046 Uiso 1 1 calc GR . . . .


_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 1.3725(13) . ?
N1 C8 1.3738(14) . ?
N1 C9 1.4486(13) . ?
C3 C2 1.4438(14) . ?
C3 C8 1.4190(14) . ?
C3 C4 1.4119(15) . ?
C2 C1 1.3664(15) . ?
C2 C17 1.5096(14) . ?
C10 C11 1.3874(15) . ?
C10 C15 1.4012(14) . ?
C10 C9 1.5106(14) . ?
C18 C19 1.3933(16) . ?
C18 C17 1.5095(14) . ?
C18 C23 1.3889(15) . ?
C1 H1 0.9300 . ?
C8 C7 1.3981(15) . ?
C7 H7 0.9300 . ?
C7 C6 1.3779(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3885(16) . ?
C4 C5 1.3866(15) . ?
C4 C24 1.5118(15) . ?
C15 C14 1.3889(16) . ?
C15 C16 1.5029(16) . ?
C19 H19 0.9300 . ?
C19 C20 1.3843(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.4050(16) . ?
C14 H14 0.9300 . ?
C14 C13 1.3820(18) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C22 1.3901(17) . ?
C6 H6 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.3887(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3818(17) . ?
C22 H22 0.9300 . ?
C22 C21 1.3800(19) . ?
C21 H21 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 108.36(9) . . ?
C1 N1 C9 125.22(9) . . ?
C8 N1 C9 126.42(9) . . ?
C8 C3 C2 106.61(9) . . ?
C4 C3 C2 134.52(10) . . ?
C4 C3 C8 118.84(9) . . ?
C3 C2 C17 129.24(9) . . ?
C1 C2 C3 106.01(9) . . ?
C1 C2 C17 124.74(10) . . ?
C11 C10 C15 119.56(10) . . ?
C11 C10 C9 121.67(9) . . ?
C15 C10 C9 118.77(9) . . ?
C19 C18 C17 120.55(10) . . ?
C23 C18 C19 118.12(10) . . ?
C23 C18 C17 121.29(10) . . ?
N1 C1 H1 124.5 . . ?
C2 C1 N1 111.02(9) . . ?
C2 C1 H1 124.5 . . ?
N1 C8 C3 108.00(9) . . ?
N1 C8 C7 129.02(10) . . ?
C7 C8 C3 122.97(10) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 C8 117.03(10) . . ?
C6 C7 H7 121.5 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.66(10) . . ?
C12 C11 H11 119.7 . . ?
C3 C4 C24 121.64(10) . . ?
C5 C4 C3 117.56(10) . . ?
C5 C4 C24 120.77(10) . . ?
C10 C15 C16 121.14(10) . . ?
C14 C15 C10 118.89(10) . . ?
C14 C15 C16 119.97(10) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.14(11) . . ?
C20 C19 H19 119.4 . . ?
N1 C9 C10 114.61(9) . . ?
N1 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C2 C17 H17A 109.3 . . ?
C2 C17 H17B 109.3 . . ?
C18 C17 C2 111.42(9) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.55(10) . . ?
C6 C5 H5 118.7 . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.30(10) . . ?
C13 C14 H14 119.3 . . ?
C4 C24 H24A 109.5 . . ?
C4 C24 H24B 109.5 . . ?
C4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C23 H23 119.5 . . ?
C18 C23 C22 120.96(11) . . ?
C22 C23 H23 119.5 . . ?
C7 C6 C5 121.05(10) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.02(12) . . ?
C21 C20 H20 120.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.88(11) . . ?
C13 C12 H12 120.1 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.23(11) . . ?
C21 C22 H22 119.9 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.52(11) . . ?
C22 C21 H21 120.2 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.64(11) . . ?
C12 C13 H13 120.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N1 C8 C7 C6 -178.26(10) . . . . ?
C3 C2 C1 N1 0.18(12) . . . . ?
C3 C2 C17 C18 -174.39(10) . . . . ?
C3 C8 C7 C6 0.17(16) . . . . ?
C3 C4 C5 C6 -0.37(16) . . . . ?
C2 C3 C8 N1 -0.37(11) . . . . ?
C2 C3 C8 C7 -179.09(9) . . . . ?
C2 C3 C4 C5 178.64(11) . . . . ?
C2 C3 C4 C24 0.61(18) . . . . ?
C10 C11 C12 C13 -0.46(17) . . . . ?
C10 C15 C14 C13 -1.98(16) . . . . ?
C18 C19 C20 C21 0.10(18) . . . . ?
C18 C23 C22 C21 0.28(17) . . . . ?
C1 N1 C8 C3 0.48(12) . . . . ?
C1 N1 C8 C7 179.10(10) . . . . ?
C1 N1 C9 C10 100.29(12) . . . . ?
C1 C2 C17 C18 4.48(15) . . . . ?
C8 N1 C1 C2 -0.42(12) . . . . ?
C8 N1 C9 C10 -79.21(13) . . . . ?
C8 C3 C2 C1 0.11(11) . . . . ?
C8 C3 C2 C17 179.14(10) . . . . ?
C8 C3 C4 C5 0.68(15) . . . . ?
C8 C3 C4 C24 -177.35(9) . . . . ?
C8 C7 C6 C5 0.16(16) . . . . ?
C11 C10 C15 C14 2.87(15) . . . . ?
C11 C10 C15 C16 -176.58(10) . . . . ?
C11 C10 C9 N1 -7.22(14) . . . . ?
C11 C12 C13 C14 1.39(18) . . . . ?
C4 C3 C2 C1 -178.02(11) . . . . ?
C4 C3 C2 C17 1.01(19) . . . . ?
C4 C3 C8 N1 178.12(9) . . . . ?
C4 C3 C8 C7 -0.60(15) . . . . ?
C4 C5 C6 C7 -0.06(17) . . . . ?
C15 C10 C11 C12 -1.69(16) . . . . ?
C15 C10 C9 N1 172.97(9) . . . . ?
C15 C14 C13 C12 -0.15(18) . . . . ?
C19 C18 C17 C2 76.82(12) . . . . ?
C19 C18 C23 C22 -1.03(16) . . . . ?
C19 C20 C21 C22 -0.87(18) . . . . ?
C9 N1 C1 C2 -179.99(9) . . . . ?
C9 N1 C8 C3 -179.95(9) . . . . ?
C9 N1 C8 C7 -1.33(18) . . . . ?
C9 C10 C11 C12 178.50(10) . . . . ?
C9 C10 C15 C14 -177.32(9) . . . . ?
C9 C10 C15 C16 3.24(15) . . . . ?
C17 C2 C1 N1 -178.90(9) . . . . ?
C17 C18 C19 C20 -176.79(10) . . . . ?
C17 C18 C23 C22 176.58(10) . . . . ?
C24 C4 C5 C6 177.67(10) . . . . ?
C23 C18 C19 C20 0.85(16) . . . . ?
C23 C18 C17 C2 -100.74(11) . . . . ?
C23 C22 C21 C20 0.69(17) . . . . ?
C16 C15 C14 C13 177.48(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd1399a
_database_code_depnum_ccdc_archive 'CCDC 1457714'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 Cl N O'
_chemical_formula_sum            'C8 H8 Cl N O'
_chemical_formula_weight         169.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.461(3)
_cell_length_b                   18.171(5)
_cell_length_c                   7.917(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.770(4)
_cell_angle_gamma                90
_cell_volume                     1578.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7742
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.2
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 'vapor diffusion of hexane into toluene'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12469
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.856
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.4856
	          2theta: -34.7367
scan:
	Number of images: 164
	           Slice: -49.0000 - 33.0000
	     Image width: 0.5000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.4856
	          2theta: -34.7367
scan:
	Number of images: 136
	           Slice: -88.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 34.4856
	          2theta: -34.7367
scan:
	Number of images: 92
	           Slice: -61.0000 - -15.0000
	     Image width: 0.5000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.4856
	          2theta: -34.7367
scan:
	Number of images: 62
	           Slice: -115.0000 - -84.0000
	     Image width: 0.5000
	        Exp time: 25.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 34.4856
	          2theta: -34.7367
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.103867
_diffrn_orient_matrix_UB_12      0.081254
_diffrn_orient_matrix_UB_13      0.003521
_diffrn_orient_matrix_UB_21      -0.020832
_diffrn_orient_matrix_UB_22      -0.024699
_diffrn_orient_matrix_UB_23      -0.044549
_diffrn_orient_matrix_UB_31      -0.063160
_diffrn_orient_matrix_UB_32      -0.040298
_diffrn_orient_matrix_UB_33      0.051877
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3489
_reflns_number_total             3617
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²+0.7660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0816
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C4(H4), C16(H16), C14(H14), C7(H7), C13(H13), C15(H15),
 C6(H6), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl -0.14083(3) 0.27016(2) 0.18326(4) 0.01962(9) Uani 1 1 d . . . . .
Cl1 Cl 0.64836(3) 0.35573(2) 0.77681(4) 0.02046(9) Uani 1 1 d . . . . .
O2 O 0.15720(8) 0.26890(5) 0.35810(13) 0.0198(2) Uani 1 1 d . . . . .
H2 H 0.2180 0.2567 0.4368 0.030 Uiso 1 1 calc GR . . . .
O1 O 0.34266(9) 0.36591(5) 0.65999(13) 0.0222(2) Uani 1 1 d . . . . .
H1 H 0.2794 0.3783 0.5862 0.033 Uiso 1 1 calc GR . . . .
N2 N 0.13657(9) 0.34458(5) 0.37085(14) 0.0162(2) Uani 1 1 d . . . . .
N1 N 0.35816(9) 0.28972(6) 0.65099(14) 0.0172(2) Uani 1 1 d . . . . .
C11 C 0.01420(11) 0.44702(7) 0.24876(15) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.47853(11) 0.18596(7) 0.76733(15) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.45587(11) 0.26626(6) 0.76282(15) 0.0145(2) Uani 1 1 d . . . . .
C10 C 0.04508(11) 0.36799(6) 0.24645(16) 0.0143(2) Uani 1 1 d . . . . .
C12 C 0.10263(12) 0.49872(7) 0.33152(17) 0.0193(3) Uani 1 1 d . . . . .
H12 H 0.1826 0.4837 0.3828 0.023 Uiso 1 1 calc R . . . .
C8 C 0.59793(11) 0.15888(7) 0.82375(16) 0.0171(2) Uani 1 1 d . . . . .
H8 H 0.6630 0.1912 0.8631 0.020 Uiso 1 1 calc R . . . .
C9 C -0.02950(11) 0.31854(7) 0.10385(16) 0.0163(2) Uani 1 1 d . . . . .
H9A H 0.0233 0.2835 0.0696 0.020 Uiso 1 1 calc R . . . .
H9B H -0.0704 0.3476 0.0010 0.020 Uiso 1 1 calc R . . . .
C1 C 0.54506(11) 0.31641(7) 0.88645(15) 0.0163(2) Uani 1 1 d . . . . .
H1A H 0.5909 0.2889 0.9892 0.020 Uiso 1 1 calc R . . . .
H1B H 0.5014 0.3554 0.9259 0.020 Uiso 1 1 calc R . . . .
C4 C 0.38163(12) 0.13646(7) 0.71179(17) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.3020 0.1539 0.6738 0.023 Uiso 1 1 calc R . . . .
C16 C -0.10545(12) 0.47073(7) 0.17103(17) 0.0188(3) Uani 1 1 d . . . . .
H16 H -0.1648 0.4371 0.1133 0.023 Uiso 1 1 calc R . . . .
C14 C -0.04789(13) 0.59533(7) 0.26255(17) 0.0219(3) Uani 1 1 d . . . . .
H14 H -0.0685 0.6446 0.2680 0.026 Uiso 1 1 calc R . . . .
C7 C 0.61917(12) 0.08355(7) 0.82091(17) 0.0217(3) Uani 1 1 d . . . . .
H7 H 0.6987 0.0659 0.8554 0.026 Uiso 1 1 calc R . . . .
C13 C 0.07183(13) 0.57218(7) 0.33765(18) 0.0223(3) Uani 1 1 d . . . . .
H13 H 0.1314 0.6062 0.3922 0.027 Uiso 1 1 calc R . . . .
C15 C -0.13583(12) 0.54471(8) 0.17998(17) 0.0220(3) Uani 1 1 d . . . . .
H15 H -0.2158 0.5600 0.1300 0.026 Uiso 1 1 calc R . . . .
C6 C 0.52281(13) 0.03471(8) 0.76708(19) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.5375 -0.0156 0.7670 0.030 Uiso 1 1 calc R . . . .
C5 C 0.40381(13) 0.06121(7) 0.71311(19) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.3389 0.0285 0.6778 0.029 Uiso 1 1 calc R . . . .


_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
Cl2 C9 1.8054(13) . ?
Cl1 C1 1.8052(13) . ?
O2 H2 0.8200 . ?
O2 N2 1.4040(13) . ?
O1 H1 0.8200 . ?
O1 N1 1.4001(13) . ?
N2 C10 1.2862(16) . ?
N1 C2 1.2835(16) . ?
C11 C10 1.4804(17) . ?
C11 C12 1.3985(17) . ?
C11 C16 1.3992(17) . ?
C3 C2 1.4807(17) . ?
C3 C8 1.4006(17) . ?
C3 C4 1.3978(18) . ?
C2 C1 1.5020(16) . ?
C10 C9 1.5019(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3852(18) . ?
C8 H8 0.9300 . ?
C8 C7 1.3916(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.3903(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3954(18) . ?
C14 H14 0.9300 . ?
C14 C13 1.3937(19) . ?
C14 C15 1.382(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(2) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.392(2) . ?
C5 H5 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
N2 O2 H2 109.5 . . ?
N1 O1 H1 109.5 . . ?
C10 N2 O2 112.70(10) . . ?
C2 N1 O1 113.05(10) . . ?
C12 C11 C10 120.92(11) . . ?
C12 C11 C16 119.01(11) . . ?
C16 C11 C10 120.05(11) . . ?
C8 C3 C2 120.16(11) . . ?
C4 C3 C2 120.57(11) . . ?
C4 C3 C8 119.26(11) . . ?
N1 C2 C3 117.13(11) . . ?
N1 C2 C1 122.83(11) . . ?
C3 C2 C1 120.04(10) . . ?
N2 C10 C11 117.15(11) . . ?
N2 C10 C9 122.63(11) . . ?
C11 C10 C9 120.22(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.41(12) . . ?
C13 C12 H12 119.8 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 119.99(12) . . ?
C7 C8 H8 120.0 . . ?
Cl2 C9 H9A 109.7 . . ?
Cl2 C9 H9B 109.7 . . ?
C10 C9 Cl2 109.61(9) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
Cl1 C1 H1A 109.6 . . ?
Cl1 C1 H1B 109.6 . . ?
C2 C1 Cl1 110.14(8) . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.24(12) . . ?
C5 C4 H4 119.9 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.10(12) . . ?
C15 C16 H16 119.9 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.66(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.51(12) . . ?
C6 C7 H7 119.7 . . ?
C12 C13 C14 120.36(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.44(12) . . ?
C14 C15 H15 119.8 . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.77(13) . . ?
C5 C6 H6 120.1 . . ?
C4 C5 C6 120.22(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?

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
O2 N2 C10 C11 179.19(10) . . . . ?
O2 N2 C10 C9 -0.41(17) . . . . ?
O1 N1 C2 C3 178.18(10) . . . . ?
O1 N1 C2 C1 -1.49(17) . . . . ?
N2 C10 C9 Cl2 82.27(13) . . . . ?
N1 C2 C1 Cl1 -83.66(13) . . . . ?
C11 C10 C9 Cl2 -97.32(12) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C16 C15 C14 1.2(2) . . . . ?
C3 C2 C1 Cl1 96.68(12) . . . . ?
C3 C8 C7 C6 -1.74(19) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C2 C3 C8 C7 -177.35(11) . . . . ?
C2 C3 C4 C5 178.72(12) . . . . ?
C10 C11 C12 C13 -177.97(12) . . . . ?
C10 C11 C16 C15 177.14(12) . . . . ?
C12 C11 C10 N2 25.05(18) . . . . ?
C12 C11 C10 C9 -155.35(12) . . . . ?
C12 C11 C16 C15 -1.39(19) . . . . ?
C8 C3 C2 N1 152.94(12) . . . . ?
C8 C3 C2 C1 -27.37(17) . . . . ?
C8 C3 C4 C5 0.15(19) . . . . ?
C8 C7 C6 C5 0.9(2) . . . . ?
C4 C3 C2 N1 -25.61(17) . . . . ?
C4 C3 C2 C1 154.07(12) . . . . ?
C4 C3 C8 C7 1.22(18) . . . . ?
C16 C11 C10 N2 -153.46(12) . . . . ?
C16 C11 C10 C9 26.14(17) . . . . ?
C16 C11 C12 C13 0.56(19) . . . . ?
C7 C6 C5 C4 0.5(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C15 C14 C13 C12 -0.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cd1400a
_database_code_depnum_ccdc_archive 'CCDC 1457715'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 N2 O'
_chemical_formula_sum            'C26 H26 N2 O'
_chemical_formula_weight         382.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

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

_cell_length_a                   6.8190(12)
_cell_length_b                   8.4731(15)
_cell_length_c                   17.387(3)
_cell_angle_alpha                91.130(4)
_cell_angle_beta                 90.978(5)
_cell_angle_gamma                96.993(4)
_cell_volume                     996.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7900
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.422
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.4933
	          2theta: -34.7450
scan:
	Number of images: 150
	           Slice: -68.0000 - 7.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.4933
	          2theta: -34.7450
scan:
	Number of images: 128
	           Slice: -9.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.4933
	          2theta: -34.7450
scan:
	Number of images: 106
	           Slice: -85.0000 - -32.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.4933
	          2theta: -34.7450
scan:
	Number of images: 62
	           Slice: -25.0000 - 6.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.4933
	          2theta: -34.7450
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.019987
_diffrn_orient_matrix_UB_12      0.077058
_diffrn_orient_matrix_UB_13      -0.124501
_diffrn_orient_matrix_UB_21      -0.107972
_diffrn_orient_matrix_UB_22      -0.042450
_diffrn_orient_matrix_UB_23      -0.026181
_diffrn_orient_matrix_UB_31      -0.025248
_diffrn_orient_matrix_UB_32      0.042702
_diffrn_orient_matrix_UB_33      0.029143
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4124
_reflns_number_total             4525
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.3900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C20(H20), C6(H6), C23(H23), C16(H16), C7(H7), C22(H22), C8(H8),
 C12(H12), C15(H15), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64768(13) 0.90408(10) 0.79100(5) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.48170(15) 0.64328(12) 0.76364(6) 0.0190(2) Uani 1 1 d . . . . .
N1 N 0.64608(15) 0.96685(12) 0.71442(6) 0.0199(2) Uani 1 1 d . . . . .
C4 C 0.19393(17) 0.73055(13) 0.72280(7) 0.0162(2) Uani 1 1 d . . . . .
C24 C 0.71411(17) 0.30767(14) 0.85620(7) 0.0170(2) Uani 1 1 d . . . . .
C19 C 0.58172(17) 0.41875(13) 0.84072(7) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.27772(17) 0.84847(14) 0.78551(7) 0.0172(2) Uani 1 1 d . . . . .
C9 C 0.31874(17) 0.61164(14) 0.71469(7) 0.0167(2) Uani 1 1 d . . . . .
C5 C 0.02385(17) 0.72588(14) 0.67820(7) 0.0185(2) Uani 1 1 d . . . . .
H5 H -0.0580 0.8055 0.6831 0.022 Uiso 1 1 calc R . . . .
C20 C 0.41429(17) 0.42194(14) 0.88529(7) 0.0184(2) Uani 1 1 d . . . . .
H20 H 0.3268 0.4948 0.8741 0.022 Uiso 1 1 calc R . . . .
C11 C 0.47279(19) 1.10373(14) 0.62403(7) 0.0198(2) Uani 1 1 d . . . . .
C6 C -0.02357(18) 0.59914(15) 0.62539(7) 0.0207(3) Uani 1 1 d . . . . .
H6 H -0.1379 0.5941 0.5950 0.025 Uiso 1 1 calc R . . . .
C1 C 0.48558(18) 1.02654(13) 0.69929(7) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.62871(17) 0.53691(14) 0.77701(7) 0.0195(2) Uani 1 1 d . . . . .
H18A H 0.7539 0.6002 0.7895 0.023 Uiso 1 1 calc R . . . .
H18B H 0.6452 0.4781 0.7296 0.023 Uiso 1 1 calc R . . . .
C21 C 0.37397(18) 0.31916(15) 0.94624(7) 0.0198(2) Uani 1 1 d . . . . .
C23 C 0.67194(19) 0.20373(14) 0.91640(7) 0.0204(2) Uani 1 1 d . . . . .
H23 H 0.7569 0.1287 0.9271 0.024 Uiso 1 1 calc R . . . .
C16 C 0.2957(2) 1.08955(15) 0.58183(8) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.1828 1.0336 0.6018 0.029 Uiso 1 1 calc R . . . .
C26 C 0.89666(18) 0.30058(15) 0.80929(7) 0.0216(3) Uani 1 1 d . . . . .
H26A H 0.8589 0.2701 0.7571 0.032 Uiso 1 1 calc GR . . . .
H26B H 0.9736 0.2238 0.8306 0.032 Uiso 1 1 calc GR . . . .
H26C H 0.9738 0.4033 0.8102 0.032 Uiso 1 1 calc GR . . . .
C2 C 0.32020(17) 1.01826(14) 0.75560(7) 0.0182(2) Uani 1 1 d . . . . .
H2A H 0.2024 1.0485 0.7307 0.022 Uiso 1 1 calc R . . . .
H2B H 0.3565 1.0920 0.7983 0.022 Uiso 1 1 calc R . . . .
C7 C 0.10021(19) 0.48121(15) 0.61844(7) 0.0211(3) Uani 1 1 d . . . . .
H7 H 0.0669 0.3976 0.5834 0.025 Uiso 1 1 calc R . . . .
C22 C 0.50522(19) 0.20973(15) 0.96096(7) 0.0211(3) Uani 1 1 d . . . . .
H22 H 0.4814 0.1395 1.0011 0.025 Uiso 1 1 calc R . . . .
C8 C 0.27345(18) 0.48502(14) 0.66280(7) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.3556 0.4056 0.6578 0.025 Uiso 1 1 calc R . . . .
C10 C 0.47932(17) 0.78984(14) 0.80653(7) 0.0180(2) Uani 1 1 d . . . . .
H10 H 0.4809 0.7667 0.8615 0.022 Uiso 1 1 calc R . . . .
C17 C 0.14184(19) 0.84519(16) 0.85501(7) 0.0225(3) Uani 1 1 d . . . . .
H17A H 0.0166 0.8763 0.8395 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.2014 0.9177 0.8943 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.1225 0.7396 0.8748 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.6404(2) 1.19111(16) 0.59419(8) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.7594 1.2015 0.6218 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2868(2) 1.15831(16) 0.51022(8) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.1690 1.1458 0.4817 0.035 Uiso 1 1 calc R . . . .
C25 C 0.1958(2) 0.32953(18) 0.99541(8) 0.0271(3) Uani 1 1 d . . . . .
H25A H 0.2232 0.4165 1.0318 0.041 Uiso 1 1 calc GR . . . .
H25B H 0.1660 0.2321 1.0225 0.041 Uiso 1 1 calc GR . . . .
H25C H 0.0848 0.3466 0.9633 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.6294(2) 1.26240(17) 0.52334(8) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.7408 1.3218 0.5040 0.037 Uiso 1 1 calc R . . . .
C14 C 0.4534(2) 1.24559(17) 0.48121(8) 0.0304(3) Uani 1 1 d . . . . .
H14 H 0.4471 1.2928 0.4335 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4438(13) . ?
O1 C10 1.4416(14) . ?
N2 C9 1.3846(16) . ?
N2 C18 1.4462(15) . ?
N2 C10 1.4378(15) . ?
N1 C1 1.2857(16) . ?
C4 C3 1.5200(16) . ?
C4 C9 1.4024(16) . ?
C4 C5 1.3802(17) . ?
C24 C19 1.4078(16) . ?
C24 C23 1.3924(17) . ?
C24 C26 1.5064(16) . ?
C19 C20 1.3934(16) . ?
C19 C18 1.5198(16) . ?
C3 C2 1.5354(17) . ?
C3 C10 1.5577(16) . ?
C3 C17 1.5339(16) . ?
C9 C8 1.3900(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.4026(17) . ?
C20 H20 0.9300 . ?
C20 C21 1.3948(17) . ?
C11 C1 1.4803(17) . ?
C11 C16 1.3933(19) . ?
C11 C12 1.3975(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.3891(18) . ?
C1 C2 1.5021(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C21 C22 1.3892(17) . ?
C21 C25 1.5076(17) . ?
C23 H23 0.9300 . ?
C23 C22 1.3921(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3886(19) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.3964(18) . ?
C22 H22 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.3875(19) . ?
C15 H15 0.9300 . ?
C15 C14 1.387(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 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
C10 O1 N1 113.89(9) . . ?
C9 N2 C18 125.21(10) . . ?
C9 N2 C10 111.92(10) . . ?
C10 N2 C18 122.61(10) . . ?
C1 N1 O1 111.95(10) . . ?
C9 C4 C3 109.10(10) . . ?
C5 C4 C3 130.37(11) . . ?
C5 C4 C9 120.52(11) . . ?
C19 C24 C26 121.31(11) . . ?
C23 C24 C19 118.13(11) . . ?
C23 C24 C26 120.56(10) . . ?
C24 C19 C18 118.92(10) . . ?
C20 C19 C24 119.76(11) . . ?
C20 C19 C18 121.28(10) . . ?
C4 C3 C2 112.14(9) . . ?
C4 C3 C10 102.91(9) . . ?
C4 C3 C17 111.58(10) . . ?
C2 C3 C10 107.89(9) . . ?
C17 C3 C2 110.44(10) . . ?
C17 C3 C10 111.62(10) . . ?
N2 C9 C4 110.25(10) . . ?
N2 C9 C8 128.54(11) . . ?
C8 C9 C4 121.21(11) . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.94(11) . . ?
C6 C5 H5 120.5 . . ?
C19 C20 H20 119.0 . . ?
C19 C20 C21 121.96(11) . . ?
C21 C20 H20 119.0 . . ?
C16 C11 C1 120.93(11) . . ?
C16 C11 C12 119.18(12) . . ?
C12 C11 C1 119.89(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.99(11) . . ?
C7 C6 H6 120.0 . . ?
N1 C1 C11 116.68(11) . . ?
N1 C1 C2 121.33(11) . . ?
C11 C1 C2 121.98(10) . . ?
N2 C18 C19 115.10(10) . . ?
N2 C18 H18A 108.5 . . ?
N2 C18 H18B 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C21 C25 120.79(11) . . ?
C22 C21 C20 117.85(11) . . ?
C22 C21 C25 121.34(11) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 C24 121.39(11) . . ?
C22 C23 H23 119.3 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.48(13) . . ?
C15 C16 H16 119.8 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 C3 109.78(9) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.68(12) . . ?
C8 C7 H7 119.2 . . ?
C21 C22 C23 120.90(11) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C9 C8 C7 117.65(11) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
O1 C10 C3 113.51(9) . . ?
O1 C10 H10 108.5 . . ?
N2 C10 O1 112.35(10) . . ?
N2 C10 C3 105.40(9) . . ?
N2 C10 H10 108.5 . . ?
C3 C10 H10 108.5 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.05(13) . . ?
C13 C12 H12 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 119.97(14) . . ?
C14 C15 H15 120.0 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(13) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.92(13) . . ?
C13 C14 H14 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C11 176.25(9) . . . . ?
O1 N1 C1 C2 -3.58(15) . . . . ?
N2 C9 C8 C7 -178.81(11) . . . . ?
N1 O1 C10 N2 69.15(12) . . . . ?
N1 O1 C10 C3 -50.31(12) . . . . ?
N1 C1 C2 C3 -47.46(15) . . . . ?
C4 C3 C2 C1 -66.93(12) . . . . ?
C4 C3 C10 O1 117.10(10) . . . . ?
C4 C3 C10 N2 -6.26(11) . . . . ?
C4 C9 C8 C7 0.63(17) . . . . ?
C4 C5 C6 C7 -0.21(17) . . . . ?
C24 C19 C20 C21 0.94(18) . . . . ?
C24 C19 C18 N2 178.23(10) . . . . ?
C24 C23 C22 C21 0.62(19) . . . . ?
C19 C24 C23 C22 -0.76(18) . . . . ?
C19 C20 C21 C22 -1.08(18) . . . . ?
C19 C20 C21 C25 177.63(11) . . . . ?
C3 C4 C9 N2 -2.63(13) . . . . ?
C3 C4 C9 C8 177.83(10) . . . . ?
C3 C4 C5 C6 -177.81(11) . . . . ?
C9 N2 C18 C19 -87.94(14) . . . . ?
C9 N2 C10 O1 -118.89(11) . . . . ?
C9 N2 C10 C3 5.20(13) . . . . ?
C9 C4 C3 C2 121.18(10) . . . . ?
C9 C4 C3 C10 5.48(12) . . . . ?
C9 C4 C3 C17 -114.33(11) . . . . ?
C9 C4 C5 C6 0.87(17) . . . . ?
C5 C4 C3 C2 -60.02(16) . . . . ?
C5 C4 C3 C10 -175.72(12) . . . . ?
C5 C4 C3 C17 64.47(16) . . . . ?
C5 C4 C9 N2 178.43(10) . . . . ?
C5 C4 C9 C8 -1.10(17) . . . . ?
C5 C6 C7 C8 -0.24(18) . . . . ?
C20 C19 C18 N2 -3.83(17) . . . . ?
C20 C21 C22 C23 0.30(18) . . . . ?
C11 C1 C2 C3 132.72(11) . . . . ?
C11 C16 C15 C14 -1.8(2) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C6 C7 C8 C9 0.03(18) . . . . ?
C1 C11 C16 C15 -178.01(12) . . . . ?
C1 C11 C12 C13 179.40(11) . . . . ?
C18 N2 C9 C4 172.43(10) . . . . ?
C18 N2 C9 C8 -8.08(19) . . . . ?
C18 N2 C10 O1 66.74(14) . . . . ?
C18 N2 C10 C3 -169.17(10) . . . . ?
C18 C19 C20 C21 -176.97(11) . . . . ?
C23 C24 C19 C20 -0.01(17) . . . . ?
C23 C24 C19 C18 177.95(11) . . . . ?
C16 C11 C1 N1 142.27(12) . . . . ?
C16 C11 C1 C2 -37.89(16) . . . . ?
C16 C11 C12 C13 -0.05(18) . . . . ?
C16 C15 C14 C13 0.8(2) . . . . ?
C26 C24 C19 C20 180.00(11) . . . . ?
C26 C24 C19 C18 -2.04(17) . . . . ?
C26 C24 C23 C22 179.24(11) . . . . ?
C2 C3 C10 O1 -1.61(13) . . . . ?
C2 C3 C10 N2 -124.96(10) . . . . ?
C10 O1 N1 C1 54.60(13) . . . . ?
C10 N2 C9 C4 -1.77(14) . . . . ?
C10 N2 C9 C8 177.72(11) . . . . ?
C10 N2 C18 C19 85.67(14) . . . . ?
C10 C3 C2 C1 45.71(12) . . . . ?
C17 C3 C2 C1 167.95(10) . . . . ?
C17 C3 C10 O1 -123.12(11) . . . . ?
C17 C3 C10 N2 113.53(11) . . . . ?
C12 C11 C1 N1 -37.17(16) . . . . ?
C12 C11 C1 C2 142.67(12) . . . . ?
C12 C11 C16 C15 1.43(19) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C25 C21 C22 C23 -178.40(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dptoi
_database_code_depnum_ccdc_archive 'CCDC 1457716'
_audit_update_record             
;
2016-03-03 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(4aR^*^,9aR^*^)-4a,9-diallyl-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino
[6,5-b]indole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.059(2)
_cell_length_b                   9.9601(19)
_cell_length_c                   11.1789(18)
_cell_angle_alpha                114.934(8)
_cell_angle_beta                 101.127(13)
_cell_angle_gamma                92.311(14)
_cell_volume                     889.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    4051
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      40.2

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 
;

_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        <1
_diffrn_reflns_number            6937
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_reduction_process 'Lp corrections applied'
_reflns_number_total             4043
_reflns_number_gt                3675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.5200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4043
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66318(9) 0.53230(9) 0.00644(8) 0.01676(19) Uani 1 1 d . . .
N1 N 0.79892(11) 0.32084(12) -0.07264(10) 0.0167(2) Uani 1 1 d . . .
N2 N 0.72589(11) 0.62271(11) -0.04765(10) 0.0163(2) Uani 1 1 d . . .
C10 C 0.83746(13) 0.27615(13) -0.19711(12) 0.0149(2) Uani 1 1 d . . .
C9 C 0.97545(14) 0.23886(13) -0.23072(12) 0.0164(2) Uani 1 1 d . . .
C4 C 0.57990(13) 0.32181(13) -0.22858(12) 0.0158(2) Uani 1 1 d . . .
C1 C 0.65229(13) 0.37208(13) -0.07605(12) 0.0152(2) Uani 1 1 d . . .
C5 C 0.71085(13) 0.26780(13) -0.29535(12) 0.0156(2) Uani 1 1 d . . .
C2 C 0.65764(13) 0.58786(13) -0.17082(12) 0.0165(2) Uani 1 1 d . . .
C11 C 0.71380(13) 0.68033(14) -0.23171(12) 0.0172(2) Uani 1 1 d . . .
C3 C 0.53099(13) 0.45957(14) -0.24616(12) 0.0169(2) Uani 1 1 d . . .
C6 C 0.71915(14) 0.21905(14) -0.42902(13) 0.0190(3) Uani 1 1 d . . .
C8 C 0.98192(14) 0.19022(14) -0.36659(13) 0.0191(3) Uani 1 1 d . . .
C20 C 0.90349(14) 0.35074(14) 0.05450(12) 0.0180(2) Uani 1 1 d . . .
C16 C 0.70958(15) 0.62123(15) -0.37020(13) 0.0207(3) Uani 1 1 d . . .
C17 C 0.44298(14) 0.19792(14) -0.28059(13) 0.0190(3) Uani 1 1 d . . .
C7 C 0.85624(15) 0.17853(14) -0.46543(13) 0.0207(3) Uani 1 1 d . . .
C12 C 0.77864(15) 0.82921(14) -0.14817(13) 0.0210(3) Uani 1 1 d . . .
C18 C 0.48176(15) 0.06805(14) -0.25171(13) 0.0217(3) Uani 1 1 d . . .
C13 C 0.83718(16) 0.91562(15) -0.20214(14) 0.0237(3) Uani 1 1 d . . .
C15 C 0.76947(15) 0.70872(15) -0.42360(13) 0.0227(3) Uani 1 1 d . . .
C14 C 0.83254(15) 0.85576(15) -0.34034(14) 0.0226(3) Uani 1 1 d . . .
C21 C 0.83381(16) 0.29400(17) 0.13865(14) 0.0250(3) Uani 1 1 d . . .
C22 C 0.8479(2) 0.3709(2) 0.27023(17) 0.0389(4) Uani 1 1 d . . .
C19 C 0.41395(19) 0.02023(18) -0.18008(16) 0.0322(3) Uani 1 1 d . . .
H3B H 0.442(2) 0.491(2) -0.2060(18) 0.039 Uiso 1 1 d . . .
H17A H 0.360(2) 0.242(2) -0.2376(18) 0.039 Uiso 1 1 d . . .
H1A H 0.590(2) 0.331(2) -0.0310(18) 0.039 Uiso 1 1 d . . .
H3A H 0.502(2) 0.437(2) -0.3444(18) 0.039 Uiso 1 1 d . . .
H20A H 0.942(2) 0.462(2) 0.1094(18) 0.039 Uiso 1 1 d . . .
H7A H 0.862(2) 0.144(2) -0.5613(18) 0.039 Uiso 1 1 d . . .
H17B H 0.408(2) 0.163(2) -0.3820(18) 0.039 Uiso 1 1 d . . .
H9A H 1.062(2) 0.248(2) -0.1645(18) 0.039 Uiso 1 1 d . . .
H8A H 1.077(2) 0.161(2) -0.3926(18) 0.039 Uiso 1 1 d . . .
H18A H 0.564(2) 0.017(2) -0.2901(18) 0.039 Uiso 1 1 d . . .
H14A H 0.871(2) 0.918(2) -0.3788(18) 0.039 Uiso 1 1 d . . .
H16A H 0.667(2) 0.516(2) -0.4292(18) 0.039 Uiso 1 1 d . . .
H20B H 0.993(2) 0.300(2) 0.0295(18) 0.039 Uiso 1 1 d . . .
H21A H 0.776(2) 0.192(2) 0.0890(18) 0.039 Uiso 1 1 d . . .
H12A H 0.780(2) 0.872(2) -0.0513(19) 0.039 Uiso 1 1 d . . .
H6A H 0.630(2) 0.211(2) -0.4973(18) 0.039 Uiso 1 1 d . . .
H13A H 0.885(2) 1.021(2) -0.1400(18) 0.039 Uiso 1 1 d . . .
H15A H 0.769(2) 0.665(2) -0.5209(18) 0.039 Uiso 1 1 d . . .
H19A H 0.443(2) -0.064(2) -0.1632(18) 0.039 Uiso 1 1 d . . .
H19B H 0.329(2) 0.072(2) -0.1391(18) 0.039 Uiso 1 1 d . . .
H22B H 0.909(2) 0.474(2) 0.3212(18) 0.039 Uiso 1 1 d . . .
H22A H 0.807(2) 0.330(2) 0.3242(18) 0.039 Uiso 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
O1 N2 1.4317(13) . ?
O1 C1 1.4554(14) . ?
N1 C10 1.3906(15) . ?
N1 C1 1.4415(15) . ?
N1 C20 1.4514(15) . ?
N2 C2 1.2844(16) . ?
C10 C9 1.3939(17) . ?
C10 C5 1.3991(17) . ?
C9 C8 1.4004(17) . ?
C9 H9A 0.939(18) . ?
C4 C5 1.5194(16) . ?
C4 C3 1.5363(17) . ?
C4 C17 1.5467(17) . ?
C4 C1 1.5525(16) . ?
C1 H1A 1.001(18) . ?
C5 C6 1.3817(17) . ?
C2 C11 1.4816(17) . ?
C2 C3 1.5033(17) . ?
C11 C16 1.3970(17) . ?
C11 C12 1.4022(18) . ?
C3 H3B 0.996(18) . ?
C3 H3A 1.001(18) . ?
C6 C7 1.4028(18) . ?
C6 H6A 0.975(18) . ?
C8 C7 1.3878(18) . ?
C8 H8A 0.979(18) . ?
C20 C21 1.5004(18) . ?
C20 H20A 1.019(18) . ?
C20 H20B 0.996(18) . ?
C16 C15 1.3913(18) . ?
C16 H16A 0.981(18) . ?
C17 C18 1.4987(18) . ?
C17 H17A 0.986(18) . ?
C17 H17B 1.012(18) . ?
C7 H7A 0.990(18) . ?
C12 C13 1.3822(18) . ?
C12 H12A 0.979(18) . ?
C18 C19 1.317(2) . ?
C18 H18A 0.980(18) . ?
C13 C14 1.3930(19) . ?
C13 H13A 1.002(18) . ?
C15 C14 1.3840(19) . ?
C15 H15A 0.986(18) . ?
C14 H14A 0.978(18) . ?
C21 C22 1.318(2) . ?
C21 H21A 0.990(18) . ?
C22 H22B 1.013(19) . ?
C22 H22A 0.977(19) . ?
C19 H19A 0.973(19) . ?
C19 H19B 1.015(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
N2 O1 C1 114.45(8) . . ?
C10 N1 C1 111.38(10) . . ?
C10 N1 C20 125.31(10) . . ?
C1 N1 C20 121.51(10) . . ?
C2 N2 O1 112.79(10) . . ?
N1 C10 C9 129.19(11) . . ?
N1 C10 C5 109.72(10) . . ?
C9 C10 C5 121.07(11) . . ?
C10 C9 C8 117.63(11) . . ?
C10 C9 H9A 121.4(11) . . ?
C8 C9 H9A 121.0(11) . . ?
C5 C4 C3 110.67(10) . . ?
C5 C4 C17 112.71(10) . . ?
C3 C4 C17 110.84(10) . . ?
C5 C4 C1 102.87(9) . . ?
C3 C4 C1 108.08(10) . . ?
C17 C4 C1 111.33(10) . . ?
N1 C1 O1 112.30(9) . . ?
N1 C1 C4 105.13(9) . . ?
O1 C1 C4 113.50(9) . . ?
N1 C1 H1A 111.0(10) . . ?
O1 C1 H1A 101.8(10) . . ?
C4 C1 H1A 113.4(10) . . ?
C6 C5 C10 120.50(11) . . ?
C6 C5 C4 130.09(11) . . ?
C10 C5 C4 109.40(10) . . ?
N2 C2 C11 115.59(11) . . ?
N2 C2 C3 120.99(11) . . ?
C11 C2 C3 123.41(11) . . ?
C16 C11 C12 118.78(12) . . ?
C16 C11 C2 121.61(11) . . ?
C12 C11 C2 119.56(11) . . ?
C2 C3 C4 109.56(10) . . ?
C2 C3 H3B 107.2(10) . . ?
C4 C3 H3B 110.0(10) . . ?
C2 C3 H3A 110.7(10) . . ?
C4 C3 H3A 110.9(10) . . ?
H3B C3 H3A 108.5(14) . . ?
C5 C6 C7 119.33(12) . . ?
C5 C6 H6A 120.1(10) . . ?
C7 C6 H6A 120.6(10) . . ?
C7 C8 C9 121.81(12) . . ?
C7 C8 H8A 119.4(10) . . ?
C9 C8 H8A 118.8(10) . . ?
N1 C20 C21 112.16(11) . . ?
N1 C20 H20A 111.5(10) . . ?
C21 C20 H20A 109.7(10) . . ?
N1 C20 H20B 105.9(10) . . ?
C21 C20 H20B 110.6(10) . . ?
H20A C20 H20B 106.8(14) . . ?
C15 C16 C11 120.38(12) . . ?
C15 C16 H16A 120.0(10) . . ?
C11 C16 H16A 119.6(10) . . ?
C18 C17 C4 112.66(10) . . ?
C18 C17 H17A 110.0(10) . . ?
C4 C17 H17A 108.3(10) . . ?
C18 C17 H17B 109.5(10) . . ?
C4 C17 H17B 107.4(10) . . ?
H17A C17 H17B 108.9(14) . . ?
C8 C7 C6 119.63(12) . . ?
C8 C7 H7A 121.3(10) . . ?
C6 C7 H7A 119.1(10) . . ?
C13 C12 C11 120.48(12) . . ?
C13 C12 H12A 120.4(11) . . ?
C11 C12 H12A 119.1(11) . . ?
C19 C18 C17 124.55(13) . . ?
C19 C18 H18A 119.6(11) . . ?
C17 C18 H18A 115.8(10) . . ?
C12 C13 C14 120.35(13) . . ?
C12 C13 H13A 118.9(10) . . ?
C14 C13 H13A 120.7(10) . . ?
C14 C15 C16 120.36(12) . . ?
C14 C15 H15A 119.9(10) . . ?
C16 C15 H15A 119.8(10) . . ?
C15 C14 C13 119.64(12) . . ?
C15 C14 H14A 120.1(10) . . ?
C13 C14 H14A 120.2(10) . . ?
C22 C21 C20 123.63(15) . . ?
C22 C21 H21A 120.8(10) . . ?
C20 C21 H21A 115.6(10) . . ?
C21 C22 H22B 120.7(10) . . ?
C21 C22 H22A 122.4(11) . . ?
H22B C22 H22A 116.8(15) . . ?
C18 C19 H19A 121.8(11) . . ?
C18 C19 H19B 120.9(10) . . ?
H19A C19 H19B 117.4(15) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.225
_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_cd0965a
_database_code_depnum_ccdc_archive 'CCDC 1481256'
_audit_update_record             
;
2016-05-22 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;
_audit_creation_date             2016-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
(4aR,9aR)-6-bromo-4a-ethyl-9-(2-methylbenzyl)-3-phenyl-4,4a,9,9a-tetrahydro-[1,2]oxazino[6,5-b]indole
_chemical_formula_moiety         'C26 H25 Br N2 O'
_chemical_formula_sum            'C26 H25 Br N2 O'
_chemical_formula_weight         461.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1842(15)
_cell_length_b                   10.542(2)
_cell_length_c                   11.953(2)
_cell_angle_alpha                84.992(11)
_cell_angle_beta                 72.078(11)
_cell_angle_gamma                74.256(11)
_cell_volume                     1059.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4684
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7087
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
scan:
	Number of images: 240
	           Slice: -125.0000 - -5.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 34.8119
	          2theta: -35.1803
scan:
	Number of images: 150
	           Slice: -106.0000 - -31.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.8119
	          2theta: -35.1803
scan:
	Number of images: 106
	           Slice: -65.0000 - -12.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.8119
	          2theta: -35.1803
scan:
	Number of images: 100
	           Slice: -65.0000 - -15.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.8119
	          2theta: -35.1803
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.107699
_diffrn_orient_matrix_UB_12      -0.045291
_diffrn_orient_matrix_UB_13      0.019456
_diffrn_orient_matrix_UB_21      0.009597
_diffrn_orient_matrix_UB_22      0.054172
_diffrn_orient_matrix_UB_23      -0.081777
_diffrn_orient_matrix_UB_31      -0.006549
_diffrn_orient_matrix_UB_32      0.073252
_diffrn_orient_matrix_UB_33      0.048195
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4223
_reflns_number_total             4807
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69412(3) 1.35008(2) 0.51573(2) 0.02701(9) Uani 1 1 d . . . . .
O1 O -0.01590(17) 1.09542(15) 0.71568(13) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.2264(2) 1.03875(18) 0.76807(17) 0.0186(4) Uani 1 1 d . . . . .
N2 N 0.0541(2) 1.10375(18) 0.58982(16) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.3489(2) 1.0945(2) 0.70676(19) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.5100(3) 1.0339(2) 0.6650(2) 0.0199(5) Uani 1 1 d . . . . .
C3 C 0.6122(3) 1.1117(2) 0.6070(2) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.5517(3) 1.2458(2) 0.5939(2) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.3903(2) 1.3078(2) 0.63657(19) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.2895(2) 1.2306(2) 0.69244(18) 0.0140(4) Uani 1 1 d . . . . .
C7 C 0.1100(2) 1.2677(2) 0.74449(19) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.0277(2) 1.3247(2) 0.6499(2) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.0687(2) 1.2208(2) 0.55904(19) 0.0154(4) Uani 1 1 d . . . . .
C10 C 0.0736(2) 1.1318(2) 0.7825(2) 0.0162(4) Uani 1 1 d . . . . .
H10 H 0.007(3) 1.135(2) 0.860(2) 0.019 Uiso 1 1 d R . . . .
C11 C 0.2451(3) 0.8981(2) 0.7845(2) 0.0200(5) Uani 1 1 d . . . . .
C12 C 0.2939(2) 0.8426(2) 0.8935(2) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.3115(2) 0.7077(2) 0.9196(2) 0.0197(5) Uani 1 1 d . . . . .
C14 C 0.3541(3) 0.6580(2) 1.0208(2) 0.0238(5) Uani 1 1 d . . . . .
C15 C 0.3816(3) 0.7376(3) 1.0943(2) 0.0272(5) Uani 1 1 d . . . . .
C16 C 0.3662(3) 0.8702(3) 1.0671(2) 0.0248(5) Uani 1 1 d . . . . .
C17 C 0.3228(3) 0.9223(2) 0.9674(2) 0.0204(5) Uani 1 1 d . . . . .
C18 C 0.2853(3) 0.6179(2) 0.8400(3) 0.0266(5) Uani 1 1 d . . . . .
C19 C 0.0531(3) 1.3650(2) 0.8465(2) 0.0177(4) Uani 1 1 d . . . . .
C20 C 0.1244(3) 1.3155(2) 0.9474(2) 0.0225(5) Uani 1 1 d . . . . .
C21 C 0.1333(2) 1.2445(2) 0.43104(19) 0.0151(4) Uani 1 1 d . . . . .
C23 C 0.2259(3) 1.3340(2) 0.3905(2) 0.0183(4) Uani 1 1 d . . . . .
C24 C 0.2929(3) 1.3503(2) 0.2708(2) 0.0211(5) Uani 1 1 d . . . . .
C25 C 0.2669(3) 1.2784(2) 0.1900(2) 0.0223(5) Uani 1 1 d . . . . .
C26 C 0.1724(3) 1.1906(2) 0.2300(2) 0.0210(5) Uani 1 1 d . . . . .
C27 C 0.1047(2) 1.1740(2) 0.3495(2) 0.0175(4) Uani 1 1 d . . . . .
H8A H 0.057(3) 1.409(2) 0.611(2) 0.021 Uiso 1 1 d R . . . .
H27 H 0.047(3) 1.116(3) 0.374(2) 0.021 Uiso 1 1 d R . . . .
H3 H 0.722(3) 1.075(2) 0.578(2) 0.021 Uiso 1 1 d R . . . .
H2 H 0.550(3) 0.945(3) 0.673(2) 0.021 Uiso 1 1 d R . . . .
H5 H 0.351(3) 1.400(3) 0.626(2) 0.021 Uiso 1 1 d R . . . .
H23 H 0.241(3) 1.383(2) 0.447(2) 0.021 Uiso 1 1 d R . . . .
H11A H 0.147(3) 0.880(2) 0.789(2) 0.021 Uiso 1 1 d R . . . .
H19A H -0.062(3) 1.388(2) 0.875(2) 0.021 Uiso 1 1 d R . . . .
H18A H 0.367(3) 0.611(3) 0.757(2) 0.026 Uiso 1 1 d R . . . .
H26 H 0.148(3) 1.139(2) 0.176(2) 0.021 Uiso 1 1 d R . . . .
H20A H 0.082(3) 1.234(3) 0.990(2) 0.026 Uiso 1 1 d R . . . .
H11B H 0.320(3) 0.851(2) 0.714(2) 0.021 Uiso 1 1 d R . . . .
H19B H 0.082(3) 1.446(3) 0.813(2) 0.021 Uiso 1 1 d R . . . .
H20B H 0.092(3) 1.383(3) 1.006(2) 0.026 Uiso 1 1 d R . . . .
H15 H 0.408(3) 0.696(2) 1.169(2) 0.021 Uiso 1 1 d R . . . .
H25 H 0.318(3) 1.288(3) 0.108(2) 0.021 Uiso 1 1 d R . . . .
H24 H 0.360(3) 1.409(2) 0.243(2) 0.021 Uiso 1 1 d R . . . .
H20C H 0.244(3) 1.294(3) 0.918(2) 0.026 Uiso 1 1 d R . . . .
H16 H 0.396(3) 0.926(2) 1.115(2) 0.021 Uiso 1 1 d R . . . .
H17 H 0.311(3) 1.013(3) 0.948(2) 0.021 Uiso 1 1 d R . . . .
H14 H 0.370(3) 0.573(3) 1.035(2) 0.021 Uiso 1 1 d R . . . .
H8B H -0.085(3) 1.348(2) 0.685(2) 0.021 Uiso 1 1 d R . . . .
H18B H 0.302(3) 0.531(3) 0.871(2) 0.026 Uiso 1 1 d R . . . .
H18C H 0.181(3) 0.647(3) 0.836(2) 0.026 Uiso 1 1 d R . . . .


_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
Br1 C4 1.908(2) . ?
O1 N2 1.448(2) . ?
O1 C10 1.445(2) . ?
N1 C1 1.387(3) . ?
N1 C10 1.447(3) . ?
N1 C11 1.448(3) . ?
N2 C9 1.287(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.92(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.94(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.95(3) . ?
C6 C7 1.523(3) . ?
C7 C8 1.540(3) . ?
C7 C10 1.557(3) . ?
C7 C19 1.532(3) . ?
C8 C9 1.501(3) . ?
C8 H8A 1.03(3) . ?
C8 H8B 0.96(3) . ?
C9 C21 1.487(3) . ?
C10 H10 0.94(3) . ?
C11 C12 1.525(3) . ?
C11 H11A 0.96(3) . ?
C11 H11B 0.98(3) . ?
C12 C13 1.405(3) . ?
C12 C17 1.398(3) . ?
C13 C14 1.399(3) . ?
C13 C18 1.510(3) . ?
C14 C15 1.386(4) . ?
C14 H14 0.88(3) . ?
C15 C16 1.386(4) . ?
C15 H15 1.02(3) . ?
C16 C17 1.392(3) . ?
C16 H16 0.99(2) . ?
C17 H17 0.95(3) . ?
C18 H18A 1.04(3) . ?
C18 H18B 0.95(3) . ?
C18 H18C 0.94(3) . ?
C19 C20 1.531(3) . ?
C19 H19A 0.97(3) . ?
C19 H19B 0.98(3) . ?
C20 H20A 1.06(3) . ?
C20 H20B 0.96(3) . ?
C20 H20C 1.01(3) . ?
C21 C23 1.397(3) . ?
C21 C27 1.401(3) . ?
C23 C24 1.388(3) . ?
C23 H23 0.95(2) . ?
C24 C25 1.391(3) . ?
C24 H24 0.96(3) . ?
C25 C26 1.393(3) . ?
C25 H25 0.96(3) . ?
C26 C27 1.388(3) . ?
C26 H26 0.99(2) . ?
C27 H27 0.89(3) . ?

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
C10 O1 N2 113.09(15) . . ?
C1 N1 C10 111.36(17) . . ?
C1 N1 C11 123.63(19) . . ?
C10 N1 C11 122.70(17) . . ?
C9 N2 O1 110.97(17) . . ?
N1 C1 C2 128.6(2) . . ?
N1 C1 C6 110.07(18) . . ?
C2 C1 C6 121.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 122.2(16) . . ?
C3 C2 H2 119.6(16) . . ?
C2 C3 H3 121.0(16) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 119.3(16) . . ?
C3 C4 Br1 118.83(16) . . ?
C3 C4 C5 122.5(2) . . ?
C5 C4 Br1 118.71(16) . . ?
C4 C5 H5 121.0(15) . . ?
C6 C5 C4 117.73(19) . . ?
C6 C5 H5 121.3(15) . . ?
C1 C6 C7 109.36(18) . . ?
C5 C6 C1 120.57(19) . . ?
C5 C6 C7 130.06(19) . . ?
C6 C7 C8 111.29(18) . . ?
C6 C7 C10 102.71(16) . . ?
C6 C7 C19 112.33(16) . . ?
C8 C7 C10 107.14(16) . . ?
C19 C7 C8 109.88(17) . . ?
C19 C7 C10 113.21(18) . . ?
C7 C8 H8A 113.3(14) . . ?
C7 C8 H8B 109.7(15) . . ?
C9 C8 C7 108.75(17) . . ?
C9 C8 H8A 110.4(14) . . ?
C9 C8 H8B 107.9(15) . . ?
H8A C8 H8B 106.6(19) . . ?
N2 C9 C8 120.7(2) . . ?
N2 C9 C21 116.58(19) . . ?
C21 C9 C8 122.71(19) . . ?
O1 C10 N1 112.29(17) . . ?
O1 C10 C7 112.67(17) . . ?
O1 C10 H10 103.2(15) . . ?
N1 C10 C7 105.36(16) . . ?
N1 C10 H10 112.6(15) . . ?
C7 C10 H10 110.9(15) . . ?
N1 C11 C12 114.36(18) . . ?
N1 C11 H11A 108.4(15) . . ?
N1 C11 H11B 109.9(15) . . ?
C12 C11 H11A 109.2(16) . . ?
C12 C11 H11B 110.3(15) . . ?
H11A C11 H11B 104(2) . . ?
C13 C12 C11 119.17(19) . . ?
C17 C12 C11 121.6(2) . . ?
C17 C12 C13 119.2(2) . . ?
C12 C13 C18 120.7(2) . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 C18 120.5(2) . . ?
C13 C14 H14 118.6(17) . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.4(17) . . ?
C14 C15 C16 119.1(2) . . ?
C14 C15 H15 117.8(14) . . ?
C16 C15 H15 123.0(14) . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.6(15) . . ?
C17 C16 H16 120.0(15) . . ?
C12 C17 H17 117.8(15) . . ?
C16 C17 C12 120.9(2) . . ?
C16 C17 H17 121.3(15) . . ?
C13 C18 H18A 112.0(14) . . ?
C13 C18 H18B 109.3(16) . . ?
C13 C18 H18C 109.6(16) . . ?
H18A C18 H18B 105(2) . . ?
H18A C18 H18C 111(2) . . ?
H18B C18 H18C 109(2) . . ?
C7 C19 H19A 109.6(15) . . ?
C7 C19 H19B 106.4(15) . . ?
C20 C19 C7 113.96(19) . . ?
C20 C19 H19A 110.8(15) . . ?
C20 C19 H19B 109.8(15) . . ?
H19A C19 H19B 106(2) . . ?
C19 C20 H20A 109.7(14) . . ?
C19 C20 H20B 110.7(16) . . ?
C19 C20 H20C 110.5(15) . . ?
H20A C20 H20B 106(2) . . ?
H20A C20 H20C 113(2) . . ?
H20B C20 H20C 106(2) . . ?
C23 C21 C9 120.87(18) . . ?
C23 C21 C27 119.3(2) . . ?
C27 C21 C9 119.84(19) . . ?
C21 C23 H23 118.0(16) . . ?
C24 C23 C21 120.5(2) . . ?
C24 C23 H23 121.5(16) . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 120.4(15) . . ?
C25 C24 H24 119.4(15) . . ?
C24 C25 C26 119.5(2) . . ?
C24 C25 H25 118.9(15) . . ?
C26 C25 H25 121.5(15) . . ?
C25 C26 H26 122.6(15) . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 116.7(15) . . ?
C21 C27 H27 120.0(17) . . ?
C26 C27 C21 119.9(2) . . ?
C26 C27 H27 120.0(17) . . ?

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
Br1 C4 C5 C6 179.85(15) . . . . ?
O1 N2 C9 C8 4.6(2) . . . . ?
O1 N2 C9 C21 -177.61(15) . . . . ?
N1 C1 C2 C3 -178.8(2) . . . . ?
N1 C1 C6 C5 178.31(18) . . . . ?
N1 C1 C6 C7 -2.6(2) . . . . ?
N1 C11 C12 C13 178.39(19) . . . . ?
N1 C11 C12 C17 -2.2(3) . . . . ?
N2 O1 C10 N1 -67.1(2) . . . . ?
N2 O1 C10 C7 51.7(2) . . . . ?
N2 C9 C21 C23 -147.59(19) . . . . ?
N2 C9 C21 C27 30.8(3) . . . . ?
C1 N1 C10 O1 111.85(19) . . . . ?
C1 N1 C10 C7 -11.1(2) . . . . ?
C1 N1 C11 C12 88.7(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C8 -118.34(19) . . . . ?
C1 C6 C7 C10 -4.0(2) . . . . ?
C1 C6 C7 C19 118.0(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 178.88(19) . . . . ?
C2 C3 C4 Br1 179.37(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -178.0(2) . . . . ?
C5 C6 C7 C8 60.6(3) . . . . ?
C5 C6 C7 C10 175.0(2) . . . . ?
C5 C6 C7 C19 -63.1(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C7 C8 C9 62.4(2) . . . . ?
C6 C7 C10 O1 -113.96(18) . . . . ?
C6 C7 C10 N1 8.8(2) . . . . ?
C6 C7 C19 C20 -57.3(3) . . . . ?
C7 C8 C9 N2 49.6(3) . . . . ?
C7 C8 C9 C21 -128.1(2) . . . . ?
C8 C7 C10 O1 3.4(2) . . . . ?
C8 C7 C10 N1 126.12(18) . . . . ?
C8 C7 C19 C20 178.19(18) . . . . ?
C8 C9 C21 C23 30.1(3) . . . . ?
C8 C9 C21 C27 -151.54(19) . . . . ?
C9 C21 C23 C24 176.4(2) . . . . ?
C9 C21 C27 C26 -176.32(19) . . . . ?
C10 O1 N2 C9 -57.7(2) . . . . ?
C10 N1 C1 C2 -172.7(2) . . . . ?
C10 N1 C1 C6 8.9(2) . . . . ?
C10 N1 C11 C12 -110.0(2) . . . . ?
C10 C7 C8 C9 -49.2(2) . . . . ?
C10 C7 C19 C20 58.4(2) . . . . ?
C11 N1 C1 C2 -9.6(3) . . . . ?
C11 N1 C1 C6 172.02(19) . . . . ?
C11 N1 C10 O1 -51.4(3) . . . . ?
C11 N1 C10 C7 -174.41(19) . . . . ?
C11 C12 C13 C14 -179.1(2) . . . . ?
C11 C12 C13 C18 1.0(3) . . . . ?
C11 C12 C17 C16 179.5(2) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 0.1(4) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C17 C12 C13 C18 -178.4(2) . . . . ?
C18 C13 C14 C15 178.8(2) . . . . ?
C19 C7 C8 C9 -172.57(17) . . . . ?
C19 C7 C10 O1 124.67(19) . . . . ?
C19 C7 C10 N1 -112.58(19) . . . . ?
C21 C23 C24 C25 0.7(3) . . . . ?
C23 C21 C27 C26 2.1(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C21 -1.0(3) . . . . ?
C27 C21 C23 C24 -1.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
