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

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

data_is_pham1482
_database_code_depnum_ccdc_archive 'CCDC 1045996'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

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

# CHEMICAL DATA

_chemical_name_systematic        
;
2-(4-Methoxyphenyl)-1-phenyl-1H-pyrrolo[3,2-b]pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

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'

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

# CRYSTAL DATA

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

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

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

_cell_length_a                   8.5374(2)
_cell_length_b                   10.3276(2)
_cell_length_c                   18.5918(3)
_cell_angle_alpha                74.9510(10)
_cell_angle_beta                 77.5080(10)
_cell_angle_gamma                84.4900(10)
_cell_volume                     1544.18(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      32.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7180
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53379
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         32.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11167
_reflns_number_gt                8411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined 
 using a riding model, with C---H = 0.98 (methyl groups), 0.99Å 
 (methylene groups), 1.00Å (methine groups) or 0.95 Å (aryl CH) and 
 with Uiso(H) = 1.5 times Ueq(C) (methyl groups) or with 
 Uiso(H) = 1.2 times Ueq(C) (methylene  groups, aryl CH,
  methine groups). Torsion angles of all methyl groups were allowed to 
  refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0453P)²+0.4232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11167
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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 0.59396(15) 0.65956(12) 0.58613(7) 0.0431(3) Uani 1 1 d . . . . .
N2 N 0.91373(12) 0.70122(10) 0.42522(6) 0.0298(2) Uani 1 1 d . . . . .
O1 O 0.87617(12) 0.57089(9) 0.10365(5) 0.0392(2) Uani 1 1 d . . . . .
C1 C 0.79691(14) 0.65374(12) 0.39742(7) 0.0302(2) Uani 1 1 d . . . . .
C2 C 0.66054(16) 0.63180(14) 0.45281(8) 0.0370(3) Uani 1 1 d . . . . .
H2 H 0.5630 0.6001 0.4484 0.044 Uiso 1 1 calc R U . . .
C3 C 0.69078(15) 0.66478(12) 0.51771(7) 0.0338(3) Uani 1 1 d . . . . .
C4 C 0.6615(2) 0.69188(14) 0.63696(8) 0.0463(4) Uani 1 1 d . . . . .
H4 H 0.5969 0.6890 0.6858 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8192(2) 0.72958(14) 0.62405(8) 0.0470(4) Uani 1 1 d . . . . .
H5 H 0.8590 0.7494 0.6638 0.056 Uiso 1 1 calc R U . . .
C6 C 0.91852(19) 0.73838(14) 0.55360(8) 0.0406(3) Uani 1 1 d . . . . .
H6 H 1.0264 0.7646 0.5430 0.049 Uiso 1 1 calc R U . . .
C7 C 0.85069(15) 0.70655(12) 0.49953(7) 0.0313(2) Uani 1 1 d . . . . .
C8 C 1.07612(14) 0.73020(11) 0.38894(6) 0.0268(2) Uani 1 1 d . . . . .
C9 C 1.13005(15) 0.85550(12) 0.38360(7) 0.0306(2) Uani 1 1 d . . . . .
H9 H 1.0584 0.9213 0.4019 0.037 Uiso 1 1 calc R U . . .
C10 C 1.28886(16) 0.88414(13) 0.35145(7) 0.0341(3) Uani 1 1 d . . . . .
H10 H 1.3264 0.9695 0.3483 0.041 Uiso 1 1 calc R U . . .
C11 C 1.39293(16) 0.78923(14) 0.32389(7) 0.0361(3) Uani 1 1 d . . . . .
H11 H 1.5019 0.8090 0.3021 0.043 Uiso 1 1 calc R U . . .
C12 C 1.33764(16) 0.66540(14) 0.32821(8) 0.0382(3) Uani 1 1 d . . . . .
H12 H 1.4087 0.6007 0.3084 0.046 Uiso 1 1 calc R U . . .
C13 C 1.17967(15) 0.63477(12) 0.36108(7) 0.0329(2) Uani 1 1 d . . . . .
H13 H 1.1426 0.5491 0.3645 0.039 Uiso 1 1 calc R U . . .
C14 C 0.82318(14) 0.63567(12) 0.32003(7) 0.0294(2) Uani 1 1 d . . . . .
C15 C 0.89601(15) 0.73097(12) 0.25664(7) 0.0316(2) Uani 1 1 d . . . . .
H15 H 0.9330 0.8099 0.2636 0.038 Uiso 1 1 calc R U . . .
C16 C 0.91575(15) 0.71349(12) 0.18376(7) 0.0317(2) Uani 1 1 d . . . . .
H16 H 0.9659 0.7797 0.1414 0.038 Uiso 1 1 calc R U . . .
C17 C 0.86189(15) 0.59871(12) 0.17300(7) 0.0302(2) Uani 1 1 d . . . . .
C18 C 0.78831(16) 0.50215(13) 0.23562(8) 0.0355(3) Uani 1 1 d . . . . .
H18 H 0.7516 0.4233 0.2284 0.043 Uiso 1 1 calc R U . . .
C19 C 0.76864(16) 0.52073(13) 0.30788(7) 0.0346(3) Uani 1 1 d . . . . .
H19 H 0.7174 0.4547 0.3501 0.041 Uiso 1 1 calc R U . . .
C20 C 0.9642(2) 0.66108(15) 0.03911(8) 0.0432(3) Uani 1 1 d . . . . .
H20A H 0.9112 0.7507 0.0331 0.065 Uiso 1 1 calc R U . . .
H20B H 0.9680 0.6292 -0.0065 0.065 Uiso 1 1 calc R U . . .
H20C H 1.0737 0.6654 0.0464 0.065 Uiso 1 1 calc R U . . .
N3 N 0.77687(13) 0.04105(10) -0.08078(6) 0.0324(2) Uani 1 1 d . . . . .
N4 N 0.58230(11) 0.18145(9) 0.07244(5) 0.02368(18) Uani 1 1 d . . . . .
O2 O 0.83666(11) 0.08650(11) 0.39014(5) 0.0393(2) Uani 1 1 d . . . . .
C21 C 0.71597(12) 0.11643(10) 0.10034(6) 0.02273(19) Uani 1 1 d . . . . .
C22 C 0.80794(13) 0.05365(11) 0.04821(6) 0.0263(2) Uani 1 1 d . . . . .
H21 H 0.9049 0.0020 0.0535 0.032 Uiso 1 1 calc R U . . .
C23 C 0.73151(13) 0.08009(10) -0.01528(6) 0.0246(2) Uani 1 1 d . . . . .
C24 C 0.67961(17) 0.08381(12) -0.13011(7) 0.0344(3) Uani 1 1 d . . . . .
H24 H 0.7084 0.0592 -0.1772 0.041 Uiso 1 1 calc R U . . .
C25 C 0.53861(16) 0.16205(12) -0.11778(7) 0.0328(3) Uani 1 1 d . . . . .
H25 H 0.4748 0.1877 -0.1556 0.039 Uiso 1 1 calc R U . . .
C26 C 0.49153(15) 0.20239(11) -0.05081(7) 0.0292(2) Uani 1 1 d . . . . .
H26 H 0.3965 0.2563 -0.0411 0.035 Uiso 1 1 calc R U . . .
C27 C 0.59087(13) 0.15970(10) 0.00137(6) 0.02285(19) Uani 1 1 d . . . . .
C28 C 0.47800(13) 0.28037(10) 0.10209(6) 0.0234(2) Uani 1 1 d . . . . .
C29 C 0.31324(14) 0.27204(11) 0.11413(7) 0.0293(2) Uani 1 1 d . . . . .
H29 H 0.2685 0.2016 0.1020 0.035 Uiso 1 1 calc R U . . .
C30 C 0.21365(16) 0.36796(13) 0.14420(8) 0.0364(3) Uani 1 1 d . . . . .
H30 H 0.1004 0.3638 0.1518 0.044 Uiso 1 1 calc R U . . .
C31 C 0.27847(17) 0.46912(13) 0.16311(8) 0.0389(3) Uani 1 1 d . . . . .
H31 H 0.2101 0.5331 0.1848 0.047 Uiso 1 1 calc R U . . .
C32 C 0.44333(17) 0.47685(12) 0.15040(8) 0.0362(3) Uani 1 1 d . . . . .
H32 H 0.4878 0.5465 0.1634 0.043 Uiso 1 1 calc R U . . .
C33 C 0.54438(15) 0.38389(11) 0.11890(7) 0.0290(2) Uani 1 1 d . . . . .
H33 H 0.6576 0.3909 0.1089 0.035 Uiso 1 1 calc R U . . .
C34 C 0.74178(13) 0.11166(10) 0.17643(6) 0.02287(19) Uani 1 1 d . . . . .
C35 C 0.61592(14) 0.10011(12) 0.23913(7) 0.0285(2) Uani 1 1 d . . . . .
H35 H 0.5089 0.0991 0.2324 0.034 Uiso 1 1 calc R U . . .
C36 C 0.64338(14) 0.09011(13) 0.31109(7) 0.0304(2) Uani 1 1 d . . . . .
H36 H 0.5559 0.0811 0.3532 0.037 Uiso 1 1 calc R U . . .
C37 C 0.79841(14) 0.09323(12) 0.32155(7) 0.0280(2) Uani 1 1 d . . . . .
C38 C 0.92620(14) 0.10371(13) 0.25978(7) 0.0307(2) Uani 1 1 d . . . . .
H38 H 1.0329 0.1051 0.2668 0.037 Uiso 1 1 calc R U . . .
C39 C 0.89805(14) 0.11214(12) 0.18831(7) 0.0278(2) Uani 1 1 d . . . . .
H39 H 0.9861 0.1184 0.1466 0.033 Uiso 1 1 calc R U . . .
C40 C 0.70924(19) 0.06299(18) 0.45538(8) 0.0477(4) Uani 1 1 d . . . . .
H40A H 0.6322 0.1400 0.4515 0.072 Uiso 1 1 calc R U . . .
H40B H 0.7532 0.0509 0.5013 0.072 Uiso 1 1 calc R U . . .
H40C H 0.6549 -0.0180 0.4581 0.072 Uiso 1 1 calc R U . . .


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

# 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 C4 1.332(2) . ?
N1 C3 1.3499(17) . ?
N2 C7 1.3834(15) . ?
N2 C1 1.3967(16) . ?
N2 C8 1.4272(15) . ?
O1 C17 1.3703(15) . ?
O1 C20 1.4267(17) . ?
C1 C2 1.3704(18) . ?
C1 C14 1.4654(17) . ?
C2 C3 1.4155(19) . ?
C2 H2 0.9500 . ?
C3 C7 1.4149(18) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3834(19) . ?
C6 H6 0.9500 . ?
C8 C13 1.3859(16) . ?
C8 C9 1.3873(16) . ?
C9 C10 1.3847(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3818(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3847(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3937(17) . ?
C14 C19 1.4028(17) . ?
C15 C16 1.3853(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3873(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3948(17) . ?
C18 C19 1.3783(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N3 C24 1.3320(17) . ?
N3 C23 1.3478(14) . ?
N4 C27 1.3823(14) . ?
N4 C21 1.3965(14) . ?
N4 C28 1.4303(13) . ?
O2 C37 1.3665(14) . ?
O2 C40 1.4284(17) . ?
C21 C22 1.3696(14) . ?
C21 C34 1.4659(15) . ?
C22 C23 1.4231(16) . ?
C22 H21 0.9500 . ?
C23 C27 1.4125(15) . ?
C24 C25 1.3945(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.3806(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.3845(16) . ?
C26 H26 0.9500 . ?
C28 C29 1.3831(16) . ?
C28 C33 1.3887(15) . ?
C29 C30 1.3918(16) . ?
C29 H29 0.9500 . ?
C30 C31 1.3811(19) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.3867(17) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.3921(15) . ?
C34 C39 1.3993(15) . ?
C35 C36 1.3837(16) . ?
C35 H35 0.9500 . ?
C36 C37 1.3833(17) . ?
C36 H36 0.9500 . ?
C37 C38 1.3918(17) . ?
C38 C39 1.3803(16) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 115.18(13) . . ?
C7 N2 C1 108.26(10) . . ?
C7 N2 C8 123.13(10) . . ?
C1 N2 C8 128.42(10) . . ?
C17 O1 C20 117.33(10) . . ?
C2 C1 N2 109.03(11) . . ?
C2 C1 C14 128.04(11) . . ?
N2 C1 C14 122.92(11) . . ?
C1 C2 C3 107.86(12) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
N1 C3 C7 122.98(13) . . ?
N1 C3 C2 129.90(13) . . ?
C7 C3 C2 107.13(11) . . ?
N1 C4 C5 125.07(13) . . ?
N1 C4 H4 117.5 . . ?
C5 C4 H4 117.5 . . ?
C6 C5 C4 120.28(14) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 115.76(14) . . ?
C7 C6 H6 122.1 . . ?
C5 C6 H6 122.1 . . ?
C6 C7 N2 131.56(12) . . ?
C6 C7 C3 120.66(12) . . ?
N2 C7 C3 107.72(11) . . ?
C13 C8 C9 120.29(11) . . ?
C13 C8 N2 121.12(10) . . ?
C9 C8 N2 118.57(10) . . ?
C10 C9 C8 119.67(11) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.33(12) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.67(12) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.62(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.40(12) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C15 C14 C19 117.83(11) . . ?
C15 C14 C1 122.60(11) . . ?
C19 C14 C1 119.53(11) . . ?
C16 C15 C14 121.64(11) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.64(11) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O1 C17 C16 124.48(11) . . ?
O1 C17 C18 115.83(11) . . ?
C16 C17 C18 119.69(12) . . ?
C19 C18 C17 120.24(11) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.96(11) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 N3 C23 115.19(10) . . ?
C27 N4 C21 108.05(8) . . ?
C27 N4 C28 124.36(9) . . ?
C21 N4 C28 125.83(9) . . ?
C37 O2 C40 117.16(10) . . ?
C22 C21 N4 109.47(9) . . ?
C22 C21 C34 127.26(10) . . ?
N4 C21 C34 123.15(9) . . ?
C21 C22 C23 107.38(10) . . ?
C21 C22 H21 126.3 . . ?
C23 C22 H21 126.3 . . ?
N3 C23 C27 123.35(10) . . ?
N3 C23 C22 129.51(10) . . ?
C27 C23 C22 107.14(9) . . ?
N3 C24 C25 124.88(11) . . ?
N3 C24 H24 117.6 . . ?
C25 C24 H24 117.6 . . ?
C26 C25 C24 120.20(11) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 116.10(11) . . ?
C25 C26 H26 122.0 . . ?
C27 C26 H26 122.0 . . ?
N4 C27 C26 131.76(10) . . ?
N4 C27 C23 107.96(9) . . ?
C26 C27 C23 120.28(10) . . ?
C29 C28 C33 120.70(10) . . ?
C29 C28 N4 120.15(9) . . ?
C33 C28 N4 119.14(10) . . ?
C28 C29 C30 119.33(11) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.40(12) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.72(11) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.65(11) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C28 119.15(11) . . ?
C32 C33 H33 120.4 . . ?
C28 C33 H33 120.4 . . ?
C35 C34 C39 117.94(10) . . ?
C35 C34 C21 122.24(10) . . ?
C39 C34 C21 119.74(10) . . ?
C36 C35 C34 121.39(11) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C37 C36 C35 119.89(11) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
O2 C37 C36 123.98(11) . . ?
O2 C37 C38 116.32(10) . . ?
C36 C37 C38 119.71(11) . . ?
C39 C38 C37 120.08(11) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 120.98(11) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
O2 C40 H40A 109.5 . . ?
O2 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O2 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C7 N2 C1 C2 1.19(14) . . . . ?
C8 N2 C1 C2 176.20(11) . . . . ?
C7 N2 C1 C14 179.90(11) . . . . ?
C8 N2 C1 C14 -5.08(18) . . . . ?
N2 C1 C2 C3 -0.49(14) . . . . ?
C14 C1 C2 C3 -179.12(11) . . . . ?
C4 N1 C3 C7 -2.43(18) . . . . ?
C4 N1 C3 C2 177.02(13) . . . . ?
C1 C2 C3 N1 -179.88(12) . . . . ?
C1 C2 C3 C7 -0.37(14) . . . . ?
C3 N1 C4 C5 0.2(2) . . . . ?
N1 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C7 -0.6(2) . . . . ?
C5 C6 C7 N2 -178.27(13) . . . . ?
C5 C6 C7 C3 -1.51(19) . . . . ?
C1 N2 C7 C6 175.68(13) . . . . ?
C8 N2 C7 C6 0.3(2) . . . . ?
C1 N2 C7 C3 -1.40(13) . . . . ?
C8 N2 C7 C3 -176.74(10) . . . . ?
N1 C3 C7 C6 3.19(19) . . . . ?
C2 C3 C7 C6 -176.37(12) . . . . ?
N1 C3 C7 N2 -179.35(11) . . . . ?
C2 C3 C7 N2 1.09(13) . . . . ?
C7 N2 C8 C13 119.88(13) . . . . ?
C1 N2 C8 C13 -54.46(17) . . . . ?
C7 N2 C8 C9 -58.59(15) . . . . ?
C1 N2 C8 C9 127.06(13) . . . . ?
C13 C8 C9 C10 -1.12(18) . . . . ?
N2 C8 C9 C10 177.37(11) . . . . ?
C8 C9 C10 C11 0.82(19) . . . . ?
C9 C10 C11 C12 0.30(19) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C9 C8 C13 C12 0.31(18) . . . . ?
N2 C8 C13 C12 -178.14(11) . . . . ?
C2 C1 C14 C15 134.12(14) . . . . ?
N2 C1 C14 C15 -44.34(17) . . . . ?
C2 C1 C14 C19 -43.58(19) . . . . ?
N2 C1 C14 C19 137.96(12) . . . . ?
C19 C14 C15 C16 -0.49(19) . . . . ?
C1 C14 C15 C16 -178.22(11) . . . . ?
C14 C15 C16 C17 0.09(19) . . . . ?
C20 O1 C17 C16 5.39(18) . . . . ?
C20 O1 C17 C18 -174.24(12) . . . . ?
C15 C16 C17 O1 -179.56(12) . . . . ?
C15 C16 C17 C18 0.06(19) . . . . ?
O1 C17 C18 C19 179.85(12) . . . . ?
C16 C17 C18 C19 0.20(19) . . . . ?
C17 C18 C19 C14 -0.6(2) . . . . ?
C15 C14 C19 C18 0.75(19) . . . . ?
C1 C14 C19 C18 178.56(12) . . . . ?
C27 N4 C21 C22 -0.31(12) . . . . ?
C28 N4 C21 C22 -165.66(10) . . . . ?
C27 N4 C21 C34 -176.45(9) . . . . ?
C28 N4 C21 C34 18.20(16) . . . . ?
N4 C21 C22 C23 0.45(12) . . . . ?
C34 C21 C22 C23 176.39(10) . . . . ?
C24 N3 C23 C27 0.48(16) . . . . ?
C24 N3 C23 C22 -179.22(12) . . . . ?
C21 C22 C23 N3 179.32(11) . . . . ?
C21 C22 C23 C27 -0.42(12) . . . . ?
C23 N3 C24 C25 -0.75(18) . . . . ?
N3 C24 C25 C26 0.8(2) . . . . ?
C24 C25 C26 C27 -0.50(17) . . . . ?
C21 N4 C27 C26 -179.11(11) . . . . ?
C28 N4 C27 C26 -13.49(18) . . . . ?
C21 N4 C27 C23 0.04(11) . . . . ?
C28 N4 C27 C23 165.66(10) . . . . ?
C25 C26 C27 N4 179.32(11) . . . . ?
C25 C26 C27 C23 0.26(16) . . . . ?
N3 C23 C27 N4 -179.53(10) . . . . ?
C22 C23 C27 N4 0.23(12) . . . . ?
N3 C23 C27 C26 -0.26(17) . . . . ?
C22 C23 C27 C26 179.49(10) . . . . ?
C27 N4 C28 C29 63.25(15) . . . . ?
C21 N4 C28 C29 -133.69(12) . . . . ?
C27 N4 C28 C33 -117.11(12) . . . . ?
C21 N4 C28 C33 45.95(15) . . . . ?
C33 C28 C29 C30 -0.70(18) . . . . ?
N4 C28 C29 C30 178.93(11) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C29 C30 C31 C32 1.5(2) . . . . ?
C30 C31 C32 C33 -0.1(2) . . . . ?
C31 C32 C33 C28 -1.74(19) . . . . ?
C29 C28 C33 C32 2.12(18) . . . . ?
N4 C28 C33 C32 -177.51(11) . . . . ?
C22 C21 C34 C35 -138.77(12) . . . . ?
N4 C21 C34 C35 36.65(15) . . . . ?
C22 C21 C34 C39 38.08(16) . . . . ?
N4 C21 C34 C39 -146.50(11) . . . . ?
C39 C34 C35 C36 0.35(17) . . . . ?
C21 C34 C35 C36 177.26(11) . . . . ?
C34 C35 C36 C37 0.82(18) . . . . ?
C40 O2 C37 C36 5.72(18) . . . . ?
C40 O2 C37 C38 -174.24(12) . . . . ?
C35 C36 C37 O2 178.75(11) . . . . ?
C35 C36 C37 C38 -1.29(18) . . . . ?
O2 C37 C38 C39 -179.46(11) . . . . ?
C36 C37 C38 C39 0.57(18) . . . . ?
C37 C38 C39 C34 0.63(18) . . . . ?
C35 C34 C39 C38 -1.08(17) . . . . ?
C21 C34 C39 C38 -178.06(10) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4

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

data_is_pham1591
_database_code_depnum_ccdc_archive 'CCDC 1045997'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

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

# CHEMICAL DATA

_chemical_name_systematic        
;
1-(4-Methoxyphenyl)-2-phenyl-1H-pyrrolo[2,3-b]pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   5.98960(10)
_cell_length_b                   11.3423(2)
_cell_length_c                   11.1347(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.3110(10)
_cell_angle_gamma                90
_cell_volume                     751.86(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6394
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      32.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7229
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14227
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.571
_diffrn_reflns_theta_max         32.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5379
_reflns_number_gt                4806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined 
 using a riding model, with C---H = 0.98 (methyl groups), 0.99Å 
 (methylene groups), 1.00Å (methine groups) or 0.95 Å (aryl CH) and 
 with Uiso(H) = 1.5 times Ueq(C) (methyl groups) or with 
 Uiso(H) = 1.2 times Ueq(C) (methylene  groups, aryl CH,
  methine groups). 
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0498P)²+0.1180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5379
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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 -0.4412(3) 0.49605(16) 0.10658(15) 0.0250(3) Uani 1 1 d . . . . .
N2 N -0.1154(3) 0.47887(14) 0.25137(14) 0.0209(3) Uani 1 1 d . . . . .
O1 O -0.0252(2) -0.00743(12) 0.20323(12) 0.0246(3) Uani 1 1 d . . . . .
C1 C -0.5712(4) 0.5755(2) 0.04351(18) 0.0285(4) Uani 1 1 d . . . . .
H1 H -0.6945 0.5468 -0.0094 0.034 Uiso 1 1 calc R U . . .
C2 C -0.5390(4) 0.6976(2) 0.04970(19) 0.0277(4) Uani 1 1 d . . . . .
H2 H -0.6377 0.7486 0.0015 0.033 Uiso 1 1 calc R U . . .
C3 C -0.3629(4) 0.74382(18) 0.12619(18) 0.0257(4) Uani 1 1 d . . . . .
H3 H -0.3387 0.8265 0.1325 0.031 Uiso 1 1 calc R U . . .
C4 C -0.2217(3) 0.66396(17) 0.19396(16) 0.0219(3) Uani 1 1 d . . . . .
C5 C -0.0262(3) 0.67085(18) 0.27968(18) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.0476 0.7410 0.3089 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0356(3) 0.55763(17) 0.31219(16) 0.0209(3) Uani 1 1 d . . . . .
C7 C -0.2729(3) 0.54319(16) 0.17870(16) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.2217(3) 0.51939(16) 0.40022(16) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.4219(3) 0.5838(2) 0.41025(18) 0.0271(4) Uani 1 1 d . . . . .
H9 H 0.4354 0.6501 0.3595 0.033 Uiso 1 1 calc R U . . .
C10 C 0.6012(3) 0.5517(2) 0.4936(2) 0.0332(5) Uani 1 1 d . . . . .
H10 H 0.7362 0.5964 0.5000 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5832(4) 0.4550(2) 0.5671(2) 0.0331(5) Uani 1 1 d . . . . .
H11 H 0.7071 0.4319 0.6227 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3843(4) 0.3916(2) 0.5598(2) 0.0310(5) Uani 1 1 d . . . . .
H12 H 0.3711 0.3261 0.6117 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2047(4) 0.42339(18) 0.47710(18) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.0689 0.3795 0.4727 0.031 Uiso 1 1 calc R U . . .
C14 C -0.0868(3) 0.35402(16) 0.24113(16) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.0938(3) 0.31077(17) 0.18708(17) 0.0233(4) Uani 1 1 d . . . . .
H15 H 0.1992 0.3638 0.1590 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1215(3) 0.18987(17) 0.17380(18) 0.0239(4) Uani 1 1 d . . . . .
H16 H 0.2454 0.1602 0.1368 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0335(3) 0.11297(16) 0.21506(16) 0.0196(3) Uani 1 1 d . . . . .
C18 C -0.2133(3) 0.15685(17) 0.27123(18) 0.0226(4) Uani 1 1 d . . . . .
H18 H -0.3173 0.1039 0.3009 0.027 Uiso 1 1 calc R U . . .
C19 C -0.2406(3) 0.27705(17) 0.28385(17) 0.0221(4) Uani 1 1 d . . . . .
H19 H -0.3637 0.3069 0.3215 0.026 Uiso 1 1 calc R U . . .
C20 C 0.1299(4) -0.05218(19) 0.1261(2) 0.0310(4) Uani 1 1 d . . . . .
H20A H 0.2833 -0.0322 0.1598 0.047 Uiso 1 1 calc R U . . .
H20B H 0.0984 -0.0170 0.0457 0.047 Uiso 1 1 calc R U . . .
H20C H 0.1144 -0.1380 0.1200 0.047 Uiso 1 1 calc R U . . .


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

# 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 C7 1.330(2) . ?
N1 C1 1.338(3) . ?
N2 C7 1.382(2) . ?
N2 C6 1.393(2) . ?
N2 C14 1.432(2) . ?
O1 C17 1.373(2) . ?
O1 C20 1.425(2) . ?
C1 C2 1.398(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 C7 1.410(3) . ?
C4 C5 1.429(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 C8 1.467(3) . ?
C8 C13 1.396(3) . ?
C8 C9 1.398(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C19 1.390(3) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 113.87(18) . . ?
C7 N2 C6 108.12(15) . . ?
C7 N2 C14 123.72(15) . . ?
C6 N2 C14 126.58(16) . . ?
C17 O1 C20 116.40(15) . . ?
N1 C1 C2 124.86(19) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C1 119.82(19) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 117.4(2) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C7 116.90(18) . . ?
C3 C4 C5 136.53(19) . . ?
C7 C4 C5 106.56(17) . . ?
C6 C5 C4 107.58(17) . . ?
C6 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
C5 C6 N2 109.26(17) . . ?
C5 C6 C8 127.98(17) . . ?
N2 C6 C8 122.71(17) . . ?
N1 C7 N2 124.38(17) . . ?
N1 C7 C4 127.14(17) . . ?
N2 C7 C4 108.47(16) . . ?
C13 C8 C9 118.57(18) . . ?
C13 C8 C6 122.64(17) . . ?
C9 C8 C6 118.76(17) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C19 120.33(17) . . ?
C15 C14 N2 119.40(16) . . ?
C19 C14 N2 120.27(16) . . ?
C14 C15 C16 120.23(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.50(17) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O1 C17 C16 124.08(16) . . ?
O1 C17 C18 115.83(16) . . ?
C16 C17 C18 120.09(17) . . ?
C19 C18 C17 120.20(17) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 119.64(17) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C7 N1 C1 C2 0.2(3) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C7 -0.4(3) . . . . ?
C2 C3 C4 C5 179.1(2) . . . . ?
C3 C4 C5 C6 -179.0(2) . . . . ?
C7 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 N2 -0.8(2) . . . . ?
C4 C5 C6 C8 -178.06(18) . . . . ?
C7 N2 C6 C5 0.6(2) . . . . ?
C14 N2 C6 C5 166.65(17) . . . . ?
C7 N2 C6 C8 178.08(16) . . . . ?
C14 N2 C6 C8 -15.9(3) . . . . ?
C1 N1 C7 N2 -179.22(18) . . . . ?
C1 N1 C7 C4 0.0(3) . . . . ?
C6 N2 C7 N1 179.17(17) . . . . ?
C14 N2 C7 N1 12.6(3) . . . . ?
C6 N2 C7 C4 -0.2(2) . . . . ?
C14 N2 C7 C4 -166.73(16) . . . . ?
C3 C4 C7 N1 0.1(3) . . . . ?
C5 C4 C7 N1 -179.61(18) . . . . ?
C3 C4 C7 N2 179.46(16) . . . . ?
C5 C4 C7 N2 -0.2(2) . . . . ?
C5 C6 C8 C13 142.0(2) . . . . ?
N2 C6 C8 C13 -34.9(3) . . . . ?
C5 C6 C8 C9 -36.0(3) . . . . ?
N2 C6 C8 C9 147.08(19) . . . . ?
C13 C8 C9 C10 1.0(3) . . . . ?
C6 C8 C9 C10 179.05(19) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -1.6(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C9 C8 C13 C12 -1.2(3) . . . . ?
C6 C8 C13 C12 -179.18(19) . . . . ?
C7 N2 C14 C15 104.0(2) . . . . ?
C6 N2 C14 C15 -59.9(2) . . . . ?
C7 N2 C14 C19 -75.2(2) . . . . ?
C6 N2 C14 C19 120.8(2) . . . . ?
C19 C14 C15 C16 0.8(3) . . . . ?
N2 C14 C15 C16 -178.51(17) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C20 O1 C17 C16 -11.0(3) . . . . ?
C20 O1 C17 C18 168.20(17) . . . . ?
C15 C16 C17 O1 178.06(18) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
O1 C17 C18 C19 -177.89(17) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C15 C14 C19 C18 -0.5(3) . . . . ?
N2 C14 C19 C18 178.73(17) . . . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

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

data_is_pham1491
_database_code_depnum_ccdc_archive 'CCDC 1045998'
_audit_update_record             
;
2015-01-28 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

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

# CHEMICAL DATA

_chemical_name_systematic        
;
2-(2-Naphthyl)-1-phenyl-1H-pyrrolo[2,3-b]pyridine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2'
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38

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'

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

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.9404(3)
_cell_length_b                   19.2009(5)
_cell_length_c                   9.6620(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3730(10)
_cell_angle_gamma                90
_cell_volume                     1657.19(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8370
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      32.29

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26989
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4828
_reflns_number_gt                3789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined 
 using a riding model, with C---H = 0.98 (methyl groups), 0.99Å 
 (methylene groups), 1.00Å (methine groups) or 0.95 Å (aryl CH) and 
 with Uiso(H) = 1.5 times Ueq(C) (methyl groups) or with 
 Uiso(H) = 1.2 times Ueq(C) (methylene  groups, aryl CH,
  methine groups). 
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0578P)²+0.4306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4828
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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 0.28231(13) 0.38580(6) 0.27300(11) 0.0311(2) Uani 1 1 d . . . . .
N2 N 0.24387(12) 0.45321(5) 0.47768(10) 0.0256(2) Uani 1 1 d . . . . .
C1 C 0.25258(14) 0.52386(6) 0.51151(12) 0.0253(2) Uani 1 1 d . . . . .
C2 C 0.28709(14) 0.56135(6) 0.39645(12) 0.0284(3) Uani 1 1 d . . . . .
H2 H 0.2980 0.6105 0.3914 0.034 Uiso 1 1 calc R U . . .
C3 C 0.30365(14) 0.51320(6) 0.28563(12) 0.0265(2) Uani 1 1 d . . . . .
C4 C 0.33728(14) 0.51675(7) 0.14591(13) 0.0304(3) Uani 1 1 d . . . . .
H4 H 0.3575 0.5600 0.1029 0.036 Uiso 1 1 calc R U . . .
C5 C 0.34002(15) 0.45505(7) 0.07270(13) 0.0332(3) Uani 1 1 d . . . . .
H5 H 0.3607 0.4555 -0.0230 0.040 Uiso 1 1 calc R U . . .
C6 C 0.31256(15) 0.39213(7) 0.13890(13) 0.0342(3) Uani 1 1 d . . . . .
H6 H 0.3155 0.3508 0.0851 0.041 Uiso 1 1 calc R U . . .
C7 C 0.27683(13) 0.44629(6) 0.33960(12) 0.0254(2) Uani 1 1 d . . . . .
C8 C 0.23450(14) 0.39594(6) 0.57149(12) 0.0251(2) Uani 1 1 d . . . . .
C9 C 0.33988(16) 0.39006(7) 0.67972(13) 0.0330(3) Uani 1 1 d . . . . .
H9 H 0.4160 0.4242 0.6927 0.040 Uiso 1 1 calc R U . . .
C10 C 0.3332(2) 0.33375(8) 0.76899(15) 0.0440(4) Uani 1 1 d . . . . .
H10 H 0.4046 0.3295 0.8441 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2237(2) 0.28391(8) 0.74945(16) 0.0515(5) Uani 1 1 d . . . . .
H11 H 0.2202 0.2451 0.8102 0.062 Uiso 1 1 calc R U . . .
C12 C 0.1187(2) 0.29054(8) 0.64110(17) 0.0512(4) Uani 1 1 d . . . . .
H12 H 0.0428 0.2563 0.6282 0.061 Uiso 1 1 calc R U . . .
C13 C 0.12324(17) 0.34659(7) 0.55125(14) 0.0367(3) Uani 1 1 d . . . . .
H13 H 0.0510 0.3511 0.4769 0.044 Uiso 1 1 calc R U . . .
C14 C 0.21732(14) 0.55104(6) 0.64854(12) 0.0253(2) Uani 1 1 d . . . . .
C15 C 0.29999(14) 0.60549(6) 0.70464(13) 0.0277(3) Uani 1 1 d . . . . .
H15 H 0.3847 0.6220 0.6583 0.033 Uiso 1 1 calc R U . . .
C16 C 0.26048(15) 0.63730(6) 0.83045(13) 0.0304(3) Uani 1 1 d . . . . .
C17 C 0.13557(15) 0.61152(7) 0.90042(13) 0.0318(3) Uani 1 1 d . . . . .
C18 C 0.05512(15) 0.55428(7) 0.84277(13) 0.0325(3) Uani 1 1 d . . . . .
H18 H -0.0274 0.5360 0.8898 0.039 Uiso 1 1 calc R U . . .
C19 C 0.09412(14) 0.52486(7) 0.72065(13) 0.0289(3) Uani 1 1 d . . . . .
H19 H 0.0383 0.4866 0.6837 0.035 Uiso 1 1 calc R U . . .
C20 C 0.34295(18) 0.69416(7) 0.88861(15) 0.0410(3) Uani 1 1 d . . . . .
H20 H 0.4268 0.7120 0.8428 0.049 Uiso 1 1 calc R U . . .
C21 C 0.3017(2) 0.72327(8) 1.01069(17) 0.0520(5) Uani 1 1 d . . . . .
H21 H 0.3576 0.7612 1.0490 0.062 Uiso 1 1 calc R U . . .
C22 C 0.1781(2) 0.69789(9) 1.08013(17) 0.0532(5) Uani 1 1 d . . . . .
H22 H 0.1512 0.7187 1.1647 0.064 Uiso 1 1 calc R U . . .
C23 C 0.09639(19) 0.64340(8) 1.02665(15) 0.0442(4) Uani 1 1 d . . . . .
H23 H 0.0127 0.6267 1.0742 0.053 Uiso 1 1 calc R U . . .


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

# 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 C7 1.3296(15) . ?
N1 C6 1.3400(17) . ?
N2 C7 1.3845(15) . ?
N2 C1 1.3968(15) . ?
N2 C8 1.4297(15) . ?
C1 C2 1.3703(17) . ?
C1 C14 1.4694(16) . ?
C2 C3 1.4269(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3968(17) . ?
C3 C7 1.4109(16) . ?
C4 C5 1.3805(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3935(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C13 1.3819(18) . ?
C8 C9 1.3828(18) . ?
C9 C10 1.3859(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3784(16) . ?
C14 C19 1.4194(17) . ?
C15 C16 1.4181(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.418(2) . ?
C16 C20 1.4202(19) . ?
C17 C18 1.4151(19) . ?
C17 C23 1.4213(18) . ?
C18 C19 1.3663(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.370(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.403(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.366(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 113.69(11) . . ?
C7 N2 C1 107.86(10) . . ?
C7 N2 C8 123.88(10) . . ?
C1 N2 C8 127.07(10) . . ?
C2 C1 N2 109.42(10) . . ?
C2 C1 C14 127.47(11) . . ?
N2 C1 C14 122.94(10) . . ?
C1 C2 C3 107.59(11) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
C4 C3 C7 116.63(11) . . ?
C4 C3 C2 136.62(12) . . ?
C7 C3 C2 106.75(10) . . ?
C5 C4 C3 117.55(12) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
C4 C5 C6 120.10(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 124.67(12) . . ?
N1 C6 H6 117.7 . . ?
C5 C6 H6 117.7 . . ?
N1 C7 N2 124.32(11) . . ?
N1 C7 C3 127.33(11) . . ?
N2 C7 C3 108.36(10) . . ?
C13 C8 C9 120.99(12) . . ?
C13 C8 N2 119.90(11) . . ?
C9 C8 N2 119.09(11) . . ?
C8 C9 C10 119.26(13) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 120.38(14) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.76(13) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.67(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 118.93(14) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C19 119.33(11) . . ?
C15 C14 C1 119.48(11) . . ?
C19 C14 C1 121.08(11) . . ?
C14 C15 C16 121.01(12) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 119.16(12) . . ?
C15 C16 C20 121.77(13) . . ?
C17 C16 C20 119.07(12) . . ?
C18 C17 C16 118.74(11) . . ?
C18 C17 C23 122.20(14) . . ?
C16 C17 C23 119.05(13) . . ?
C19 C18 C17 121.15(13) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 120.57(12) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C16 120.03(16) . . ?
C21 C20 H20 120.0 . . ?
C16 C20 H20 120.0 . . ?
C20 C21 C22 121.04(15) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.31(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C17 120.50(16) . . ?
C22 C23 H23 119.7 . . ?
C17 C23 H23 119.7 . . ?

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
C7 N2 C1 C2 1.32(14) . . . . ?
C8 N2 C1 C2 169.13(12) . . . . ?
C7 N2 C1 C14 177.01(11) . . . . ?
C8 N2 C1 C14 -15.18(19) . . . . ?
N2 C1 C2 C3 -1.00(14) . . . . ?
C14 C1 C2 C3 -176.45(12) . . . . ?
C1 C2 C3 C4 -179.98(14) . . . . ?
C1 C2 C3 C7 0.31(14) . . . . ?
C7 C3 C4 C5 0.59(18) . . . . ?
C2 C3 C4 C5 -179.09(14) . . . . ?
C3 C4 C5 C6 -1.15(19) . . . . ?
C7 N1 C6 C5 1.5(2) . . . . ?
C4 C5 C6 N1 0.1(2) . . . . ?
C6 N1 C7 N2 178.34(12) . . . . ?
C6 N1 C7 C3 -2.21(19) . . . . ?
C1 N2 C7 N1 178.44(12) . . . . ?
C8 N2 C7 N1 10.15(19) . . . . ?
C1 N2 C7 C3 -1.10(14) . . . . ?
C8 N2 C7 C3 -169.39(11) . . . . ?
C4 C3 C7 N1 1.20(19) . . . . ?
C2 C3 C7 N1 -179.03(12) . . . . ?
C4 C3 C7 N2 -179.28(11) . . . . ?
C2 C3 C7 N2 0.49(14) . . . . ?
C7 N2 C8 C13 -65.42(17) . . . . ?
C1 N2 C8 C13 128.59(14) . . . . ?
C7 N2 C8 C9 113.07(14) . . . . ?
C1 N2 C8 C9 -52.92(17) . . . . ?
C13 C8 C9 C10 0.0(2) . . . . ?
N2 C8 C9 C10 -178.53(12) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C9 C8 C13 C12 -0.2(2) . . . . ?
N2 C8 C13 C12 178.23(12) . . . . ?
C11 C12 C13 C8 0.0(2) . . . . ?
C2 C1 C14 C15 -41.94(18) . . . . ?
N2 C1 C14 C15 143.17(12) . . . . ?
C2 C1 C14 C19 134.40(14) . . . . ?
N2 C1 C14 C19 -40.48(17) . . . . ?
C19 C14 C15 C16 -2.34(18) . . . . ?
C1 C14 C15 C16 174.07(11) . . . . ?
C14 C15 C16 C17 1.24(18) . . . . ?
C14 C15 C16 C20 -178.98(12) . . . . ?
C15 C16 C17 C18 0.59(17) . . . . ?
C20 C16 C17 C18 -179.20(12) . . . . ?
C15 C16 C17 C23 179.87(12) . . . . ?
C20 C16 C17 C23 0.09(18) . . . . ?
C16 C17 C18 C19 -1.31(19) . . . . ?
C23 C17 C18 C19 179.44(12) . . . . ?
C17 C18 C19 C14 0.22(19) . . . . ?
C15 C14 C19 C18 1.62(18) . . . . ?
C1 C14 C19 C18 -174.73(12) . . . . ?
C15 C16 C20 C21 -179.68(13) . . . . ?
C17 C16 C20 C21 0.1(2) . . . . ?
C16 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C21 C22 C23 C17 0.2(2) . . . . ?
C18 C17 C23 C22 179.00(13) . . . . ?
C16 C17 C23 C22 -0.3(2) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

