# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_P-2-aza6helicene
_database_code_depnum_ccdc_archive 'CCDC 1521681'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H15 N'
_chemical_formula_moiety         'C25 H15 N'
_chemical_formula_weight         329.40
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.25647(18)
_cell_length_b                   13.0278(4)
_cell_length_c                   17.2343(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1629.27(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15514
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.942

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18570
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         4.254
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2992
_reflns_number_gt                2492
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1559
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2992
_refine_ls_number_parameters     236
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0880P)²+0.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_abs_structure_details 
;
 Flack x determined using 771 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
N2 N 0.5424(6) 0.4891(3) 0.3827(2) 0.0618(11) Uani 1 1 d . . . . .
C1 C 0.5629(6) 0.5250(3) 0.4556(2) 0.0464(10) Uani 1 1 d . . . . .
H1 H 0.4579 0.5253 0.4885 0.056 Uiso 1 1 calc R U . . .
C3 C 0.7002(7) 0.4875(4) 0.3362(3) 0.0614(14) Uani 1 1 d . . . . .
H3 H 0.6912 0.4595 0.2855 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8632(6) 0.5234(4) 0.3600(3) 0.0616(14) Uani 1 1 d . . . . .
H4 H 0.9656 0.5218 0.3257 0.074 Uiso 1 1 calc R U . . .
C5 C 0.8848(5) 0.5637(4) 0.4357(3) 0.0545(12) Uani 1 1 d . . . . .
C6 C 1.0528(6) 0.6114(5) 0.4601(4) 0.0709(16) Uani 1 1 d . . . . .
H6 H 1.1605 0.6052 0.4291 0.085 Uiso 1 1 calc R U . . .
C7 C 1.0587(7) 0.6651(5) 0.5265(4) 0.0735(16) Uani 1 1 d . . . . .
H7 H 1.1681 0.7012 0.5397 0.088 Uiso 1 1 calc R U . . .
C8 C 0.9045(6) 0.6691(4) 0.5781(3) 0.0597(13) Uani 1 1 d . . . . .
C9 C 0.9011(9) 0.7382(4) 0.6418(4) 0.0768(18) Uani 1 1 d . . . . .
H9 H 1.0080 0.7771 0.6539 0.092 Uiso 1 1 calc R U . . .
C10 C 0.7482(10) 0.7492(4) 0.6850(4) 0.0752(17) Uani 1 1 d . . . . .
H10 H 0.7431 0.8031 0.7221 0.090 Uiso 1 1 calc R U . . .
C11 C 0.5962(8) 0.6837(4) 0.6770(3) 0.0643(14) Uani 1 1 d . . . . .
C12 C 0.4321(9) 0.6959(5) 0.7216(3) 0.0737(17) Uani 1 1 d . . . . .
H12 H 0.4226 0.7518 0.7568 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2903(9) 0.6298(5) 0.7147(3) 0.0761(17) Uani 1 1 d . . . . .
H13 H 0.1767 0.6442 0.7398 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3093(6) 0.5400(4) 0.6709(3) 0.0597(13) Uani 1 1 d . . . . .
C15 C 0.1617(6) 0.4653(5) 0.6679(3) 0.0682(16) Uani 1 1 d . . . . .
H15 H 0.0459 0.4818 0.6904 0.082 Uiso 1 1 calc R U . . .
C16 C 0.1849(6) 0.3724(5) 0.6336(3) 0.0682(16) Uani 1 1 d . . . . .
H16 H 0.0826 0.3279 0.6266 0.082 Uiso 1 1 calc R U . . .
C17 C 0.3630(5) 0.3422(4) 0.6083(3) 0.0532(12) Uani 1 1 d . . . . .
C18 C 0.4016(6) 0.2397(4) 0.5871(3) 0.0591(13) Uani 1 1 d . . . . .
H18 H 0.3029 0.1924 0.5817 0.071 Uiso 1 1 calc R U . . .
C19 C 0.5758(7) 0.2077(4) 0.5743(3) 0.0617(13) Uani 1 1 d . . . . .
H19 H 0.5980 0.1381 0.5607 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7223(6) 0.2749(3) 0.5809(2) 0.0465(10) Uani 1 1 d . . . . .
H20 H 0.8453 0.2513 0.5749 0.056 Uiso 1 1 calc R U . . .
C21 C 0.6878(5) 0.3736(3) 0.5957(2) 0.0456(10) Uani 1 1 d . . . . .
H21 H 0.7888 0.4199 0.5974 0.055 Uiso 1 1 calc R U . . .
C22 C 0.5100(5) 0.4125(4) 0.6089(2) 0.0467(10) Uani 1 1 d . . . . .
C23 C 0.4754(6) 0.5188(4) 0.6315(2) 0.0495(11) Uani 1 1 d . . . . .
C24 C 0.6084(6) 0.6008(3) 0.6227(2) 0.0477(10) Uani 1 1 d . . . . .
C25 C 0.7490(6) 0.6061(3) 0.5639(3) 0.0483(10) Uani 1 1 d . . . . .
C26 C 0.7323(5) 0.5627(3) 0.4863(2) 0.0440(10) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
N2 C1 1.349(6) . ?
N2 C3 1.397(6) . ?
C1 C26 1.426(6) . ?
C1 H1 0.9500 . ?
C3 C4 1.336(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(7) . ?
C4 H4 0.9500 . ?
C5 C26 1.409(6) . ?
C5 C6 1.431(7) . ?
C6 C7 1.343(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.430(8) . ?
C7 H7 0.9500 . ?
C8 C25 1.417(6) . ?
C8 C9 1.420(8) . ?
C9 C10 1.344(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.426(7) . ?
C11 C24 1.431(7) . ?
C12 C13 1.347(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(8) . ?
C13 H13 0.9500 . ?
C14 C23 1.411(6) . ?
C14 C15 1.448(7) . ?
C15 C16 1.358(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.419(7) . ?
C16 H16 0.9500 . ?
C17 C22 1.407(6) . ?
C17 C18 1.411(7) . ?
C18 C19 1.350(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.335(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.406(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.460(7) . ?
C23 C24 1.447(6) . ?
C24 C25 1.441(6) . ?
C25 C26 1.456(6) . ?

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 N2 C3 116.6(4) . . ?
N2 C1 C26 124.1(4) . . ?
N2 C1 H1 118.0 . . ?
C26 C1 H1 118.0 . . ?
C4 C3 N2 123.0(4) . . ?
C4 C3 H3 118.5 . . ?
N2 C3 H3 118.5 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C26 C5 C4 118.7(4) . . ?
C26 C5 C6 119.4(5) . . ?
C4 C5 C6 121.7(5) . . ?
C7 C6 C5 120.2(5) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.6(5) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C25 C8 C9 119.2(5) . . ?
C25 C8 C7 119.6(5) . . ?
C9 C8 C7 121.1(5) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 122.0(5) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 122.4(6) . . ?
C10 C11 C24 118.4(5) . . ?
C12 C11 C24 119.2(5) . . ?
C13 C12 C11 121.2(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C23 120.5(5) . . ?
C13 C14 C15 120.6(5) . . ?
C23 C14 C15 118.9(5) . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C22 C17 C18 117.9(4) . . ?
C22 C17 C16 120.5(5) . . ?
C18 C17 C16 121.5(5) . . ?
C19 C18 C17 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 120.7(5) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 118.8(4) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 123.4(4) . . ?
C20 C21 H21 118.3 . . ?
C22 C21 H21 118.3 . . ?
C21 C22 C17 117.4(4) . . ?
C21 C22 C23 122.9(4) . . ?
C17 C22 C23 119.3(4) . . ?
C14 C23 C24 118.4(4) . . ?
C14 C23 C22 117.5(4) . . ?
C24 C23 C22 123.9(4) . . ?
C11 C24 C25 117.9(4) . . ?
C11 C24 C23 116.6(4) . . ?
C25 C24 C23 125.5(4) . . ?
C8 C25 C24 118.0(4) . . ?
C8 C25 C26 116.7(4) . . ?
C24 C25 C26 124.7(4) . . ?
C5 C26 C1 116.8(4) . . ?
C5 C26 C25 120.0(4) . . ?
C1 C26 C25 123.1(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
C3 N2 C1 C26 1.4(6) . . . . ?
C1 N2 C3 C4 -2.9(7) . . . . ?
N2 C3 C4 C5 1.4(8) . . . . ?
C3 C4 C5 C26 1.7(7) . . . . ?
C3 C4 C5 C6 -174.0(5) . . . . ?
C26 C5 C6 C7 -7.7(7) . . . . ?
C4 C5 C6 C7 168.0(5) . . . . ?
C5 C6 C7 C8 5.4(8) . . . . ?
C6 C7 C8 C25 7.4(7) . . . . ?
C6 C7 C8 C9 -170.1(5) . . . . ?
C25 C8 C9 C10 -4.5(7) . . . . ?
C7 C8 C9 C10 173.0(5) . . . . ?
C8 C9 C10 C11 9.4(8) . . . . ?
C9 C10 C11 C12 -178.8(5) . . . . ?
C9 C10 C11 C24 2.1(8) . . . . ?
C10 C11 C12 C13 -177.7(5) . . . . ?
C24 C11 C12 C13 1.4(7) . . . . ?
C11 C12 C13 C14 8.1(8) . . . . ?
C12 C13 C14 C23 -1.7(7) . . . . ?
C12 C13 C14 C15 175.7(5) . . . . ?
C13 C14 C15 C16 -172.0(5) . . . . ?
C23 C14 C15 C16 5.5(7) . . . . ?
C14 C15 C16 C17 7.7(7) . . . . ?
C15 C16 C17 C22 -8.6(7) . . . . ?
C15 C16 C17 C18 166.9(5) . . . . ?
C22 C17 C18 C19 5.7(7) . . . . ?
C16 C17 C18 C19 -169.9(5) . . . . ?
C17 C18 C19 C20 -0.7(7) . . . . ?
C18 C19 C20 C21 -3.8(7) . . . . ?
C19 C20 C21 C22 3.2(7) . . . . ?
C20 C21 C22 C17 1.8(6) . . . . ?
C20 C21 C22 C23 174.7(4) . . . . ?
C18 C17 C22 C21 -6.1(6) . . . . ?
C16 C17 C22 C21 169.6(4) . . . . ?
C18 C17 C22 C23 -179.2(4) . . . . ?
C16 C17 C22 C23 -3.5(6) . . . . ?
C13 C14 C23 C24 -13.8(6) . . . . ?
C15 C14 C23 C24 168.8(4) . . . . ?
C13 C14 C23 C22 160.3(4) . . . . ?
C15 C14 C23 C22 -17.2(6) . . . . ?
C21 C22 C23 C14 -156.4(4) . . . . ?
C17 C22 C23 C14 16.3(6) . . . . ?
C21 C22 C23 C24 17.3(6) . . . . ?
C17 C22 C23 C24 -170.0(4) . . . . ?
C10 C11 C24 C25 -18.1(6) . . . . ?
C12 C11 C24 C25 162.9(4) . . . . ?
C10 C11 C24 C23 162.7(4) . . . . ?
C12 C11 C24 C23 -16.4(6) . . . . ?
C14 C23 C24 C11 22.3(6) . . . . ?
C22 C23 C24 C11 -151.3(4) . . . . ?
C14 C23 C24 C25 -156.9(4) . . . . ?
C22 C23 C24 C25 29.5(6) . . . . ?
C9 C8 C25 C24 -11.4(6) . . . . ?
C7 C8 C25 C24 171.0(4) . . . . ?
C9 C8 C25 C26 160.4(4) . . . . ?
C7 C8 C25 C26 -17.1(6) . . . . ?
C11 C24 C25 C8 22.5(6) . . . . ?
C23 C24 C25 C8 -158.3(4) . . . . ?
C11 C24 C25 C26 -148.7(4) . . . . ?
C23 C24 C25 C26 30.5(6) . . . . ?
C4 C5 C26 C1 -3.0(6) . . . . ?
C6 C5 C26 C1 172.8(4) . . . . ?
C4 C5 C26 C25 -178.4(4) . . . . ?
C6 C5 C26 C25 -2.6(6) . . . . ?
N2 C1 C26 C5 1.4(6) . . . . ?
N2 C1 C26 C25 176.7(4) . . . . ?
C8 C25 C26 C5 14.7(6) . . . . ?
C24 C25 C26 C5 -174.0(4) . . . . ?
C8 C25 C26 C1 -160.4(4) . . . . ?
C24 C25 C26 C1 10.9(7) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
(P)-(+)-Benzo(5,6)phenanthro(3,4-h)isoquinoline
_chemical_name_common            (P)-(+)-2-Aza(6)helicene
####################################################################### 
# 
# 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_M-1-aza6helicene
_database_code_depnum_ccdc_archive 'CCDC 1521682'
_audit_update_record             
;
2016-12-09 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H15 N'
_chemical_formula_moiety         'C25 H15 N'
_chemical_formula_weight         329.40
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.29278(13)
_cell_length_b                   12.9794(2)
_cell_length_c                   17.3679(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1643.98(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24154
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  0.931

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            25821
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_theta_max         68.217
_diffrn_reflns_theta_min         4.252
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2998
_reflns_number_gt                2631
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1093
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     236
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(9)
_refine_ls_abs_structure_details 
;
 Flack x determined using 973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.3207(3) 0.38401(18) 0.59767(12) 0.0512(6) Uani 1 1 d . . . . .
C2 C 0.2974(4) 0.2840(2) 0.57973(14) 0.0549(7) Uani 1 1 d . . . . .
H2 H 0.1762 0.2596 0.5714 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4421(5) 0.2147(3) 0.57275(16) 0.0676(9) Uani 1 1 d . . . . .
H3 H 0.4205 0.1456 0.5571 0.081 Uiso 1 1 calc R U . . .
C4 C 0.6146(5) 0.2478(3) 0.58874(18) 0.0712(10) Uani 1 1 d . . . . .
H4 H 0.7148 0.2012 0.5852 0.085 Uiso 1 1 calc R U . . .
C5 C 0.6454(4) 0.3499(3) 0.61035(17) 0.0628(9) Uani 1 1 d . . . . .
C6 C 0.8210(5) 0.3859(4) 0.6367(2) 0.0812(12) Uani 1 1 d . . . . .
H6 H 0.9263 0.3435 0.6305 0.097 Uiso 1 1 calc R U . . .
C7 C 0.8374(4) 0.4782(4) 0.6698(2) 0.0844(13) Uani 1 1 d . . . . .
H7 H 0.9514 0.4973 0.6920 0.101 Uiso 1 1 calc R U . . .
C8 C 0.6880(4) 0.5492(3) 0.67248(17) 0.0674(9) Uani 1 1 d . . . . .
C9 C 0.7004(6) 0.6419(3) 0.71525(18) 0.0844(13) Uani 1 1 d . . . . .
H9 H 0.8125 0.6598 0.7397 0.101 Uiso 1 1 calc R U . . .
C10 C 0.5546(6) 0.7045(3) 0.72135(17) 0.0794(11) Uani 1 1 d . . . . .
H10 H 0.5594 0.7609 0.7562 0.095 Uiso 1 1 calc R U . . .
C11 C 0.3929(5) 0.6885(3) 0.67686(16) 0.0644(9) Uani 1 1 d . . . . .
C12 C 0.2388(6) 0.7541(3) 0.6842(2) 0.0775(11) Uani 1 1 d . . . . .
H12 H 0.2410 0.8083 0.7209 0.093 Uiso 1 1 calc R U . . .
C13 C 0.0895(5) 0.7408(2) 0.6401(2) 0.0736(10) Uani 1 1 d . . . . .
H13 H -0.0184 0.7793 0.6506 0.088 Uiso 1 1 calc R U . . .
C14 C 0.0909(4) 0.6696(2) 0.57746(17) 0.0579(8) Uani 1 1 d . . . . .
C15 C -0.0598(4) 0.6646(3) 0.5264(2) 0.0673(9) Uani 1 1 d . . . . .
H15 H -0.1692 0.7007 0.5387 0.081 Uiso 1 1 calc R U . . .
C16 C -0.0513(4) 0.6100(3) 0.4609(2) 0.0693(9) Uani 1 1 d . . . . .
H16 H -0.1574 0.6031 0.4296 0.083 Uiso 1 1 calc R U . . .
C17 C 0.1178(4) 0.5616(2) 0.43762(17) 0.0531(7) Uani 1 1 d . . . . .
C18 C 0.1393(4) 0.5214(3) 0.36320(18) 0.0637(9) Uani 1 1 d . . . . .
H18 H 0.0372 0.5199 0.3292 0.076 Uiso 1 1 calc R U . . .
C19 C 0.3035(5) 0.4847(3) 0.33907(17) 0.0647(9) Uani 1 1 d . . . . .
H19 H 0.3164 0.4569 0.2888 0.078 Uiso 1 1 calc R U . . .
C20 C 0.4535(4) 0.4881(2) 0.38881(17) 0.0551(7) Uani 1 1 d . . . . .
H20 H 0.5694 0.4642 0.3715 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4365(3) 0.5254(2) 0.46229(14) 0.0420(6) Uani 1 1 d . . . . .
H21 H 0.5404 0.5269 0.4953 0.050 Uiso 1 1 calc R U . . .
C22 C 0.2681(4) 0.56111(18) 0.48893(15) 0.0432(6) Uani 1 1 d . . . . .
C23 C 0.2477(4) 0.60734(19) 0.56514(14) 0.0449(6) Uani 1 1 d . . . . .
C24 C 0.3876(4) 0.6048(2) 0.62424(14) 0.0494(7) Uani 1 1 d . . . . .
C25 C 0.5227(4) 0.5257(2) 0.63348(14) 0.0504(7) Uani 1 1 d . . . . .
C26 C 0.4952(3) 0.4197(2) 0.61147(14) 0.0485(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.345(4) . ?
N1 C26 1.375(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 C26 1.421(4) . ?
C5 C6 1.438(5) . ?
C6 C7 1.335(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.427(5) . ?
C7 H7 0.9500 . ?
C8 C25 1.416(4) . ?
C8 C9 1.417(5) . ?
C9 C10 1.343(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.425(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(5) . ?
C11 C24 1.421(4) . ?
C12 C13 1.343(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.414(5) . ?
C14 C23 1.416(4) . ?
C15 C16 1.342(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.441(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(5) . ?
C17 C22 1.413(3) . ?
C18 C19 1.356(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.461(3) . ?
C23 C24 1.448(4) . ?
C24 C25 1.431(4) . ?
C25 C26 1.443(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C26 118.8(2) . . ?
N1 C2 C3 123.2(3) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C26 119.0(3) . . ?
C4 C5 C6 122.5(3) . . ?
C26 C5 C6 118.4(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C25 C8 C9 119.2(3) . . ?
C25 C8 C7 119.7(3) . . ?
C9 C8 C7 121.1(4) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C24 119.7(3) . . ?
C12 C11 C10 121.4(3) . . ?
C24 C11 C10 118.9(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C23 120.4(3) . . ?
C15 C14 C13 120.1(3) . . ?
C23 C14 C13 119.4(3) . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 C16 121.0(3) . . ?
C22 C17 C16 119.3(3) . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 118.5(2) . . ?
C21 C22 C23 121.9(2) . . ?
C17 C22 C23 119.4(2) . . ?
C14 C23 C24 118.4(2) . . ?
C14 C23 C22 117.0(2) . . ?
C24 C23 C22 124.1(2) . . ?
C11 C24 C25 117.2(3) . . ?
C11 C24 C23 117.2(3) . . ?
C25 C24 C23 125.5(2) . . ?
C8 C25 C24 119.1(3) . . ?
C8 C25 C26 116.7(3) . . ?
C24 C25 C26 124.0(2) . . ?
N1 C26 C5 119.7(3) . . ?
N1 C26 C25 119.7(2) . . ?
C5 C26 C25 120.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C26 N1 C2 C3 -1.4(4) . . . . ?
N1 C2 C3 C4 3.6(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C26 -3.2(4) . . . . ?
C3 C4 C5 C6 172.4(3) . . . . ?
C4 C5 C6 C7 -167.8(3) . . . . ?
C26 C5 C6 C7 7.8(5) . . . . ?
C5 C6 C7 C8 -7.2(5) . . . . ?
C6 C7 C8 C25 -5.7(4) . . . . ?
C6 C7 C8 C9 172.7(3) . . . . ?
C25 C8 C9 C10 2.8(4) . . . . ?
C7 C8 C9 C10 -175.6(3) . . . . ?
C8 C9 C10 C11 -9.2(5) . . . . ?
C9 C10 C11 C12 179.2(3) . . . . ?
C9 C10 C11 C24 -0.7(4) . . . . ?
C24 C11 C12 C13 -2.5(5) . . . . ?
C10 C11 C12 C13 177.5(3) . . . . ?
C11 C12 C13 C14 -8.6(5) . . . . ?
C12 C13 C14 C15 -173.0(3) . . . . ?
C12 C13 C14 C23 4.2(4) . . . . ?
C23 C14 C15 C16 -7.3(4) . . . . ?
C13 C14 C15 C16 169.9(3) . . . . ?
C14 C15 C16 C17 -5.2(4) . . . . ?
C15 C16 C17 C18 -167.7(3) . . . . ?
C15 C16 C17 C22 8.0(4) . . . . ?
C22 C17 C18 C19 -1.9(4) . . . . ?
C16 C17 C18 C19 173.7(3) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C21 1.7(4) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C17 -2.4(4) . . . . ?
C20 C21 C22 C23 -176.1(2) . . . . ?
C18 C17 C22 C21 3.4(4) . . . . ?
C16 C17 C22 C21 -172.3(2) . . . . ?
C18 C17 C22 C23 177.2(2) . . . . ?
C16 C17 C22 C23 1.5(4) . . . . ?
C15 C14 C23 C24 -171.9(2) . . . . ?
C13 C14 C23 C24 10.9(3) . . . . ?
C15 C14 C23 C22 16.2(3) . . . . ?
C13 C14 C23 C22 -161.0(2) . . . . ?
C21 C22 C23 C14 160.4(2) . . . . ?
C17 C22 C23 C14 -13.2(3) . . . . ?
C21 C22 C23 C24 -11.0(4) . . . . ?
C17 C22 C23 C24 175.4(2) . . . . ?
C12 C11 C24 C25 -163.5(2) . . . . ?
C10 C11 C24 C25 16.4(4) . . . . ?
C12 C11 C24 C23 17.4(4) . . . . ?
C10 C11 C24 C23 -162.7(3) . . . . ?
C14 C23 C24 C11 -21.3(3) . . . . ?
C22 C23 C24 C11 150.0(2) . . . . ?
C14 C23 C24 C25 159.7(2) . . . . ?
C22 C23 C24 C25 -29.0(4) . . . . ?
C9 C8 C25 C24 13.3(4) . . . . ?
C7 C8 C25 C24 -168.3(2) . . . . ?
C9 C8 C25 C26 -161.3(2) . . . . ?
C7 C8 C25 C26 17.1(4) . . . . ?
C11 C24 C25 C8 -22.6(3) . . . . ?
C23 C24 C25 C8 156.5(2) . . . . ?
C11 C24 C25 C26 151.6(2) . . . . ?
C23 C24 C25 C26 -29.3(4) . . . . ?
C2 N1 C26 C5 -3.1(4) . . . . ?
C2 N1 C26 C25 -177.8(2) . . . . ?
C4 C5 C26 N1 5.4(4) . . . . ?
C6 C5 C26 N1 -170.4(3) . . . . ?
C4 C5 C26 C25 -179.9(3) . . . . ?
C6 C5 C26 C25 4.3(4) . . . . ?
C8 C25 C26 N1 158.3(2) . . . . ?
C24 C25 C26 N1 -16.0(4) . . . . ?
C8 C25 C26 C5 -16.4(3) . . . . ?
C24 C25 C26 C5 169.3(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        (M)-(-)--Benzo(5,6)phenanthro(3,4-h)quinoline
_chemical_name_common            (M)-(-)-1-Aza(6)helicene
