# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1P_100K
_database_code_depnum_ccdc_archive 'CCDC 1895789'
loop_
_audit_author_name
_audit_author_address
'Dr. Parthapratim Munshi '
;Department of Chemistry and Shiv Nadar University
India
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   14.2215(2)
_cell_length_b                   14.2215(2)
_cell_length_c                   15.6241(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3159.99(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.22

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8874
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   XRAY
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30662
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6445
_reflns_number_gt                5821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.5771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6445
_refine_ls_number_parameters     561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1B N 0.12673(14) 0.50074(14) 0.37033(13) 0.0168(4) Uani 1 1 d . . . . .
N1A N 0.96041(15) 0.37750(14) 0.61260(13) 0.0166(4) Uani 1 1 d . . . . .
N2B N 0.10520(14) 0.42541(13) 0.49436(12) 0.0160(4) Uani 1 1 d . . . . .
N2A N 0.88586(14) 0.35505(14) 0.73684(13) 0.0171(4) Uani 1 1 d . . . . .
C15A C 0.81742(17) 0.39190(17) 0.51515(15) 0.0178(5) Uani 1 1 d . . . . .
C2B C 0.11180(16) 0.50919(16) 0.45643(15) 0.0152(5) Uani 1 1 d . . . . .
C10B C 0.14502(17) 0.25720(17) 0.27694(15) 0.0174(5) Uani 1 1 d . . . . .
C9B C 0.13114(16) 0.20846(16) 0.35853(15) 0.0165(5) Uani 1 1 d . . . . .
C3B C 0.11777(16) 0.36056(16) 0.42919(14) 0.0151(5) Uani 1 1 d . . . . .
C1A C 0.86558(17) 0.37669(16) 0.59414(15) 0.0158(5) Uani 1 1 d . . . . .
C15B C 0.14486(17) 0.35717(17) 0.27311(15) 0.0170(5) Uani 1 1 d . . . . .
C16B C 0.10516(16) 0.59967(17) 0.50133(15) 0.0161(5) Uani 1 1 d . . . . .
C20B C 0.06050(19) 0.68897(18) 0.62646(16) 0.0228(6) Uani 1 1 d . . . . .
C14B C 0.16053(18) 0.40305(18) 0.19506(16) 0.0200(5) Uani 1 1 d . . . . .
C4A C 0.72043(17) 0.35967(16) 0.67719(15) 0.0179(5) Uani 1 1 d . . . . .
C3A C 0.82103(17) 0.36149(16) 0.67117(14) 0.0165(5) Uani 1 1 d . . . . .
C2A C 0.96925(17) 0.36418(16) 0.69878(15) 0.0169(5) Uani 1 1 d . . . . .
C21A C 1.06250(19) 0.33063(18) 0.82848(15) 0.0203(5) Uani 1 1 d . . . . .
C1B C 0.13014(17) 0.40576(16) 0.35231(15) 0.0159(5) Uani 1 1 d . . . . .
C4B C 0.11977(16) 0.25999(17) 0.43557(15) 0.0163(5) Uani 1 1 d . . . . .
C5B C 0.11321(17) 0.21247(18) 0.51444(16) 0.0191(5) Uani 1 1 d . . . . .
C20A C 1.14694(19) 0.32408(18) 0.87192(16) 0.0228(6) Uani 1 1 d . . . . .
C11B C 0.16195(17) 0.20840(18) 0.19972(16) 0.0198(5) Uani 1 1 d . . . . .
C16A C 1.06015(17) 0.35898(17) 0.74301(15) 0.0169(5) Uani 1 1 d . . . . .
C18A C 1.22944(18) 0.37298(18) 0.74700(16) 0.0206(5) Uani 1 1 d . . . . .
C8B C 0.13175(18) 0.10927(18) 0.36439(17) 0.0212(5) Uani 1 1 d . . . . .
C17B C 0.13427(17) 0.68380(18) 0.46286(15) 0.0191(5) Uani 1 1 d . . . . .
C5A C 0.67331(18) 0.34213(18) 0.75463(16) 0.0208(5) Uani 1 1 d . . . . .
C12B C 0.17718(19) 0.25511(19) 0.12390(16) 0.0230(6) Uani 1 1 d . . . . .
C10A C 0.71739(17) 0.39208(18) 0.51888(16) 0.0199(5) Uani 1 1 d . . . . .
C6A C 0.57657(19) 0.34061(19) 0.75793(17) 0.0236(6) Uani 1 1 d . . . . .
C9A C 0.66866(17) 0.37571(17) 0.60078(16) 0.0197(5) Uani 1 1 d . . . . .
C19B C 0.08705(18) 0.77310(18) 0.58800(16) 0.0217(5) Uani 1 1 d . . . . .
C6B C 0.11638(18) 0.11582(18) 0.51759(16) 0.0213(5) Uani 1 1 d . . . . .
C13B C 0.17671(19) 0.35326(19) 0.12128(15) 0.0225(5) Uani 1 1 d . . . . .
C14A C 0.86365(19) 0.40710(18) 0.43682(16) 0.0213(5) Uani 1 1 d . . . . .
C12A C 0.7148(2) 0.42150(19) 0.36596(18) 0.0265(6) Uani 1 1 d . . . . .
C7B C 0.12441(19) 0.06426(19) 0.44186(18) 0.0239(6) Uani 1 1 d . . . . .
C21B C 0.06884(18) 0.60381(18) 0.58418(16) 0.0212(5) Uani 1 1 d . . . . .
C8A C 0.56987(19) 0.37437(19) 0.60673(18) 0.0246(6) Uani 1 1 d . . . . .
C11A C 0.66821(19) 0.40722(19) 0.44198(18) 0.0244(6) Uani 1 1 d . . . . .
C17A C 1.14504(17) 0.38082(17) 0.70246(16) 0.0188(5) Uani 1 1 d . . . . .
C18B C 0.12523(18) 0.76864(18) 0.50586(16) 0.0212(5) Uani 1 1 d . . . . .
C19A C 1.23219(18) 0.34435(18) 0.83224(16) 0.0220(6) Uani 1 1 d . . . . .
C13A C 0.8132(2) 0.42179(19) 0.36306(17) 0.0251(6) Uani 1 1 d . . . . .
C7A C 0.52481(19) 0.35750(19) 0.68333(18) 0.0265(6) Uani 1 1 d . . . . .
C22B C 0.0738(2) 0.8661(2) 0.6329(2) 0.0301(7) Uani 1 1 d . . . . .
C22A C 1.3237(2) 0.3336(2) 0.8792(2) 0.0307(6) Uani 1 1 d . . . . .
H11B H 0.1655(18) 0.1401(19) 0.1993(17) 0.015(6) Uiso 1 1 d . . . . .
H12B H 0.1914(19) 0.218(2) 0.0735(18) 0.020(7) Uiso 1 1 d . . . . .
H13B H 0.188(2) 0.387(2) 0.0671(18) 0.027(8) Uiso 1 1 d . . . . .
H14B H 0.1625(19) 0.473(2) 0.1947(18) 0.023(7) Uiso 1 1 d . . . . .
H7B H 0.1247(18) -0.006(2) 0.4451(18) 0.024(7) Uiso 1 1 d . . . . .
H6B H 0.1121(19) 0.083(2) 0.5734(18) 0.022(7) Uiso 1 1 d . . . . .
H5B H 0.109(2) 0.248(2) 0.5676(19) 0.026(7) Uiso 1 1 d . . . . .
H8B H 0.1407(19) 0.0729(19) 0.3125(17) 0.019(7) Uiso 1 1 d . . . . .
H17B H 0.1621(18) 0.6830(18) 0.4047(17) 0.016(7) Uiso 1 1 d . . . . .
H18B H 0.1458(19) 0.827(2) 0.4772(17) 0.021(7) Uiso 1 1 d . . . . .
H21B H 0.0487(19) 0.5439(19) 0.6121(16) 0.020(7) Uiso 1 1 d . . . . .
H20B H 0.0344(19) 0.688(2) 0.6852(18) 0.027(8) Uiso 1 1 d . . . . .
H6A H 0.543(2) 0.327(2) 0.8131(19) 0.034(8) Uiso 1 1 d . . . . .
H7A H 0.456(2) 0.357(2) 0.688(2) 0.039(9) Uiso 1 1 d . . . . .
H5A H 0.711(2) 0.329(2) 0.8039(19) 0.032(8) Uiso 1 1 d . . . . .
H8A H 0.532(2) 0.387(2) 0.556(2) 0.032(8) Uiso 1 1 d . . . . .
H14A H 0.934(2) 0.4085(19) 0.4335(18) 0.022(7) Uiso 1 1 d . . . . .
H13A H 0.844(2) 0.432(2) 0.3080(19) 0.028(8) Uiso 1 1 d . . . . .
H12A H 0.677(2) 0.432(2) 0.313(2) 0.031(8) Uiso 1 1 d . . . . .
H11A H 0.597(2) 0.411(2) 0.4403(19) 0.030(8) Uiso 1 1 d . . . . .
H18A H 1.2889(19) 0.3868(17) 0.7171(16) 0.016(7) Uiso 1 1 d . . . . .
H17A H 1.1447(19) 0.4008(19) 0.6408(17) 0.021(7) Uiso 1 1 d . . . . .
H20A H 1.1492(19) 0.3039(19) 0.9320(19) 0.024(7) Uiso 1 1 d . . . . .
H21A H 1.004(2) 0.314(2) 0.8563(19) 0.028(8) Uiso 1 1 d . . . . .
H1NB H 0.127(2) 0.551(2) 0.3316(19) 0.026(8) Uiso 1 1 d . . . . .
H1NA H 1.006(2) 0.3884(19) 0.5746(17) 0.019(7) Uiso 1 1 d . . . . .
H22D H 0.059(2) 0.856(2) 0.694(3) 0.053(10) Uiso 1 1 d . . . . .
H22E H 0.127(3) 0.907(3) 0.626(2) 0.053(10) Uiso 1 1 d . . . . .
H22F H 0.020(3) 0.902(3) 0.607(3) 0.082(14) Uiso 1 1 d . . . . .
H22A H 1.368(3) 0.378(3) 0.861(3) 0.069(13) Uiso 1 1 d . . . . .
H22B H 1.319(3) 0.336(3) 0.940(3) 0.079(14) Uiso 1 1 d . . . . .
H22C H 1.356(3) 0.274(3) 0.869(3) 0.074(13) 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
N1B C2B 1.367(3) . ?
N1B C1B 1.381(3) . ?
N1B H1NB 0.93(3) . ?
N1A C2A 1.365(3) . ?
N1A C1A 1.379(3) . ?
N1A H1NA 0.89(3) . ?
N2B C2B 1.334(3) . ?
N2B C3B 1.385(3) . ?
N2A C2A 1.333(3) . ?
N2A C3A 1.382(3) . ?
C15A C14A 1.406(4) . ?
C15A C10A 1.424(3) . ?
C15A C1A 1.428(3) . ?
C2B C16B 1.469(3) . ?
C10B C11B 1.413(3) . ?
C10B C15B 1.423(3) . ?
C10B C9B 1.464(3) . ?
C9B C8B 1.414(3) . ?
C9B C4B 1.418(3) . ?
C3B C1B 1.374(3) . ?
C3B C4B 1.434(3) . ?
C1A C3A 1.377(3) . ?
C15B C14B 1.401(3) . ?
C15B C1B 1.433(3) . ?
C16B C21B 1.395(3) . ?
C16B C17B 1.401(3) . ?
C20B C21B 1.385(4) . ?
C20B C19B 1.391(4) . ?
C20B H20B 0.99(3) . ?
C14B C13B 1.372(4) . ?
C14B H14B 0.99(3) . ?
C4A C5A 1.405(3) . ?
C4A C9A 1.421(3) . ?
C4A C3A 1.434(3) . ?
C2A C16A 1.468(3) . ?
C21A C20A 1.383(4) . ?
C21A C16A 1.395(3) . ?
C21A H21A 0.96(3) . ?
C4B C5B 1.409(3) . ?
C5B C6B 1.376(4) . ?
C5B H5B 0.97(3) . ?
C20A C19A 1.392(4) . ?
C20A H20A 0.98(3) . ?
C11B C12B 1.375(4) . ?
C11B H11B 0.97(3) . ?
C16A C17A 1.398(3) . ?
C18A C17A 1.392(4) . ?
C18A C19A 1.393(3) . ?
C18A H18A 0.99(3) . ?
C8B C7B 1.373(4) . ?
C8B H8B 0.97(3) . ?
C17B C18B 1.387(4) . ?
C17B H17B 0.99(3) . ?
C5A C6A 1.377(4) . ?
C5A H5A 0.96(3) . ?
C12B C13B 1.396(4) . ?
C12B H12B 0.97(3) . ?
C10A C11A 1.407(4) . ?
C10A C9A 1.474(4) . ?
C6A C7A 1.399(4) . ?
C6A H6A 1.01(3) . ?
C9A C8A 1.408(4) . ?
C19B C18B 1.395(4) . ?
C19B C22B 1.509(4) . ?
C6B C7B 1.397(4) . ?
C6B H6B 0.99(3) . ?
C13B H13B 0.99(3) . ?
C14A C13A 1.374(4) . ?
C14A H14A 1.00(3) . ?
C12A C11A 1.375(4) . ?
C12A C13A 1.400(4) . ?
C12A H12A 0.99(3) . ?
C7B H7B 1.00(3) . ?
C21B H21B 1.00(3) . ?
C8A C7A 1.379(4) . ?
C8A H8A 0.97(3) . ?
C11A H11A 1.01(3) . ?
C17A H17A 1.00(3) . ?
C18B H18B 0.99(3) . ?
C19A C22A 1.502(4) . ?
C13A H13A 0.98(3) . ?
C7A H7A 0.99(3) . ?
C22B H22D 0.99(4) . ?
C22B H22E 0.96(4) . ?
C22B H22F 1.01(4) . ?
C22A H22A 0.93(5) . ?
C22A H22B 0.96(5) . ?
C22A H22C 0.97(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
C2B N1B C1B 107.0(2) . . ?
C2B N1B H1NB 125.0(18) . . ?
C1B N1B H1NB 127.7(18) . . ?
C2A N1A C1A 107.2(2) . . ?
C2A N1A H1NA 128.0(17) . . ?
C1A N1A H1NA 124.7(17) . . ?
C2B N2B C3B 105.01(19) . . ?
C2A N2A C3A 104.82(19) . . ?
C14A C15A C10A 120.2(2) . . ?
C14A C15A C1A 123.5(2) . . ?
C10A C15A C1A 116.4(2) . . ?
N2B C2B N1B 111.7(2) . . ?
N2B C2B C16B 124.5(2) . . ?
N1B C2B C16B 123.8(2) . . ?
C11B C10B C15B 117.1(2) . . ?
C11B C10B C9B 122.3(2) . . ?
C15B C10B C9B 120.6(2) . . ?
C8B C9B C4B 117.5(2) . . ?
C8B C9B C10B 121.9(2) . . ?
C4B C9B C10B 120.6(2) . . ?
C1B C3B N2B 110.3(2) . . ?
C1B C3B C4B 121.7(2) . . ?
N2B C3B C4B 128.0(2) . . ?
C3A C1A N1A 105.6(2) . . ?
C3A C1A C15A 123.9(2) . . ?
N1A C1A C15A 130.4(2) . . ?
C14B C15B C10B 120.1(2) . . ?
C14B C15B C1B 123.4(2) . . ?
C10B C15B C1B 116.5(2) . . ?
C21B C16B C17B 118.1(2) . . ?
C21B C16B C2B 120.3(2) . . ?
C17B C16B C2B 121.6(2) . . ?
C21B C20B C19B 121.5(2) . . ?
C21B C20B H20B 117.8(17) . . ?
C19B C20B H20B 120.7(17) . . ?
C13B C14B C15B 121.2(2) . . ?
C13B C14B H14B 120.4(16) . . ?
C15B C14B H14B 118.4(16) . . ?
C5A C4A C9A 120.3(2) . . ?
C5A C4A C3A 122.4(2) . . ?
C9A C4A C3A 117.3(2) . . ?
C1A C3A N2A 110.6(2) . . ?
C1A C3A C4A 121.3(2) . . ?
N2A C3A C4A 128.0(2) . . ?
N2A C2A N1A 111.8(2) . . ?
N2A C2A C16A 124.7(2) . . ?
N1A C2A C16A 123.5(2) . . ?
C20A C21A C16A 120.7(2) . . ?
C20A C21A H21A 120.5(18) . . ?
C16A C21A H21A 118.8(18) . . ?
C3B C1B N1B 106.0(2) . . ?
C3B C1B C15B 123.2(2) . . ?
N1B C1B C15B 130.8(2) . . ?
C5B C4B C9B 120.1(2) . . ?
C5B C4B C3B 122.6(2) . . ?
C9B C4B C3B 117.3(2) . . ?
C6B C5B C4B 120.6(2) . . ?
C6B C5B H5B 119.2(17) . . ?
C4B C5B H5B 120.2(17) . . ?
C21A C20A C19A 121.6(2) . . ?
C21A C20A H20A 121.1(16) . . ?
C19A C20A H20A 117.3(16) . . ?
C12B C11B C10B 121.7(2) . . ?
C12B C11B H11B 118.0(16) . . ?
C10B C11B H11B 120.3(16) . . ?
C21A C16A C17A 118.5(2) . . ?
C21A C16A C2A 119.1(2) . . ?
C17A C16A C2A 122.4(2) . . ?
C17A C18A C19A 121.7(2) . . ?
C17A C18A H18A 119.1(15) . . ?
C19A C18A H18A 119.2(15) . . ?
C7B C8B C9B 121.5(2) . . ?
C7B C8B H8B 119.8(16) . . ?
C9B C8B H8B 118.6(16) . . ?
C18B C17B C16B 120.5(2) . . ?
C18B C17B H17B 119.4(15) . . ?
C16B C17B H17B 120.1(15) . . ?
C6A C5A C4A 120.8(2) . . ?
C6A C5A H5A 122.0(18) . . ?
C4A C5A H5A 117.2(18) . . ?
C11B C12B C13B 120.5(2) . . ?
C11B C12B H12B 118.2(16) . . ?
C13B C12B H12B 121.3(16) . . ?
C11A C10A C15A 117.5(2) . . ?
C11A C10A C9A 122.1(2) . . ?
C15A C10A C9A 120.3(2) . . ?
C5A C6A C7A 119.4(2) . . ?
C5A C6A H6A 120.9(18) . . ?
C7A C6A H6A 119.6(18) . . ?
C8A C9A C4A 117.3(2) . . ?
C8A C9A C10A 121.9(2) . . ?
C4A C9A C10A 120.7(2) . . ?
C20B C19B C18B 117.6(2) . . ?
C20B C19B C22B 121.3(2) . . ?
C18B C19B C22B 121.1(2) . . ?
C5B C6B C7B 119.8(2) . . ?
C5B C6B H6B 120.2(16) . . ?
C7B C6B H6B 120.0(16) . . ?
C14B C13B C12B 119.5(2) . . ?
C14B C13B H13B 119.9(17) . . ?
C12B C13B H13B 120.6(17) . . ?
C13A C14A C15A 120.6(2) . . ?
C13A C14A H14A 118.4(16) . . ?
C15A C14A H14A 121.0(16) . . ?
C11A C12A C13A 120.6(2) . . ?
C11A C12A H12A 118.8(18) . . ?
C13A C12A H12A 120.6(17) . . ?
C8B C7B C6B 120.5(2) . . ?
C8B C7B H7B 120.6(16) . . ?
C6B C7B H7B 118.8(16) . . ?
C20B C21B C16B 120.8(2) . . ?
C20B C21B H21B 120.9(15) . . ?
C16B C21B H21B 118.4(15) . . ?
C7A C8A C9A 121.6(3) . . ?
C7A C8A H8A 118.8(19) . . ?
C9A C8A H8A 119.6(19) . . ?
C12A C11A C10A 121.4(2) . . ?
C12A C11A H11A 116.8(17) . . ?
C10A C11A H11A 121.8(17) . . ?
C18A C17A C16A 120.0(2) . . ?
C18A C17A H17A 120.4(16) . . ?
C16A C17A H17A 119.5(16) . . ?
C17B C18B C19B 121.4(2) . . ?
C17B C18B H18B 119.1(15) . . ?
C19B C18B H18B 119.5(15) . . ?
C20A C19A C18A 117.5(2) . . ?
C20A C19A C22A 121.1(2) . . ?
C18A C19A C22A 121.4(3) . . ?
C14A C13A C12A 119.7(2) . . ?
C14A C13A H13A 121.5(17) . . ?
C12A C13A H13A 118.9(17) . . ?
C8A C7A C6A 120.6(2) . . ?
C8A C7A H7A 121.6(19) . . ?
C6A C7A H7A 117.9(19) . . ?
C19B C22B H22D 111(2) . . ?
C19B C22B H22E 112(2) . . ?
H22D C22B H22E 111(3) . . ?
C19B C22B H22F 111(3) . . ?
H22D C22B H22F 108(3) . . ?
H22E C22B H22F 104(3) . . ?
C19A C22A H22A 112(3) . . ?
C19A C22A H22B 115(3) . . ?
H22A C22A H22B 109(4) . . ?
C19A C22A H22C 114(3) . . ?
H22A C22A H22C 103(3) . . ?
H22B C22A H22C 103(3) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_1N_298K
_database_code_depnum_ccdc_archive 'CCDC 1895794'
loop_
_audit_author_name
_audit_author_address
'Dr. Parthapratim Munshi'
;Department of Chemistry and Shiv Nadar University
India
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

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

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

_cell_length_a                   19.2160(4)
_cell_length_b                   19.2160(4)
_cell_length_c                   8.9740(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3313.69(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9373
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.36

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8720
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Xray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22529
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3382
_reflns_number_gt                3099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.3680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3382
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.22380(8) 0.31121(9) 0.51451(19) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.25085(8) 0.35389(8) 0.73869(18) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.29558(9) 0.31423(9) 0.5208(2) 0.0314(4) Uani 1 1 d . . . . .
C15 C 0.34698(9) 0.29915(9) 0.4102(2) 0.0322(4) Uani 1 1 d . . . . .
C2 C 0.19992(10) 0.33658(9) 0.6464(2) 0.0332(4) Uani 1 1 d . . . . .
C4 C 0.38179(9) 0.35339(9) 0.7040(2) 0.0335(4) Uani 1 1 d . . . . .
C3 C 0.31108(9) 0.34034(9) 0.6594(2) 0.0311(4) Uani 1 1 d . . . . .
C10 C 0.41713(10) 0.31294(10) 0.4497(2) 0.0359(4) Uani 1 1 d . . . . .
C16 C 0.12580(10) 0.34367(10) 0.6843(2) 0.0376(4) Uani 1 1 d . . . . .
C9 C 0.43458(10) 0.34102(11) 0.5971(2) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.46843(11) 0.29893(13) 0.3420(3) 0.0487(5) Uani 1 1 d . . . . .
C14 C 0.33118(11) 0.27331(11) 0.2675(2) 0.0391(4) Uani 1 1 d . . . . .
C5 C 0.39901(11) 0.37900(11) 0.8455(2) 0.0416(5) Uani 1 1 d . . . . .
C17 C 0.07577(11) 0.29828(14) 0.6316(3) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.38289(12) 0.26172(12) 0.1652(3) 0.0458(5) Uani 1 1 d . . . . .
C12 C 0.45173(12) 0.27436(13) 0.2034(3) 0.0504(6) Uani 1 1 d . . . . .
C6 C 0.46705(12) 0.39326(13) 0.8815(3) 0.0515(6) Uani 1 1 d . . . . .
C8 C 0.50353(12) 0.35743(14) 0.6376(3) 0.0516(6) Uani 1 1 d . . . . .
C21 C 0.10615(12) 0.39525(14) 0.7847(3) 0.0584(6) Uani 1 1 d . . . . .
C7 C 0.51907(11) 0.38336(15) 0.7765(3) 0.0563(6) Uani 1 1 d . . . . .
C18 C 0.00718(13) 0.30497(16) 0.6765(3) 0.0642(7) Uani 1 1 d . . . . .
C20 C 0.03752(15) 0.40057(17) 0.8292(4) 0.0745(9) Uani 1 1 d . . . . .
C19 C -0.01279(12) 0.35580(16) 0.7753(4) 0.0680(7) Uani 1 1 d . . . . .
C22 C -0.08808(19) 0.3609(3) 0.8259(8) 0.1097(16) Uani 1 1 d . . . . .
H7 H 0.5675(14) 0.3945(13) 0.798(3) 0.056(7) Uiso 1 1 d . . . . .
H5 H 0.3632(12) 0.3886(11) 0.920(3) 0.039(6) Uiso 1 1 d . . . . .
H6 H 0.4785(12) 0.4122(13) 0.982(3) 0.049(6) Uiso 1 1 d . . . . .
H8 H 0.5431(15) 0.3514(13) 0.564(3) 0.061(7) Uiso 1 1 d . . . . .
H14 H 0.2848(13) 0.2636(12) 0.246(3) 0.046(6) Uiso 1 1 d . . . . .
H13 H 0.3704(14) 0.2481(14) 0.065(3) 0.061(8) Uiso 1 1 d . . . . .
H12 H 0.4899(17) 0.2624(16) 0.136(3) 0.076(9) Uiso 1 1 d . . . . .
H11 H 0.5192(15) 0.3043(14) 0.366(3) 0.062(8) Uiso 1 1 d . . . . .
H18 H -0.0286(17) 0.2715(15) 0.642(3) 0.071(8) Uiso 1 1 d . . . . .
H17 H 0.0921(17) 0.2608(16) 0.560(4) 0.083(10) Uiso 1 1 d . . . . .
H21 H 0.1421(16) 0.4305(16) 0.825(4) 0.087(10) Uiso 1 1 d . . . . .
H20 H 0.0265(18) 0.4352(19) 0.894(4) 0.095(12) Uiso 1 1 d . . . . .
H1N H 0.1980(14) 0.2949(14) 0.437(3) 0.058(7) Uiso 1 1 d . . . . .
H22A H -0.087(3) 0.389(3) 0.918(7) 0.17(2) Uiso 1 1 d . . . . .
H22B H -0.101(2) 0.406(3) 0.757(5) 0.126(16) Uiso 1 1 d . . . . .
H22C H -0.119(4) 0.329(5) 0.728(10) 0.27(4) 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
N1 C2 1.360(3) . ?
N1 C1 1.382(2) . ?
N1 H1N 0.91(3) . ?
N2 C2 1.325(2) . ?
N2 C3 1.384(2) . ?
C1 C3 1.374(3) . ?
C1 C15 1.430(3) . ?
C15 C14 1.406(3) . ?
C15 C10 1.419(3) . ?
C2 C16 1.471(3) . ?
C4 C5 1.402(3) . ?
C4 C9 1.416(3) . ?
C4 C3 1.439(3) . ?
C10 C11 1.407(3) . ?
C10 C9 1.468(3) . ?
C16 C17 1.381(3) . ?
C16 C21 1.392(3) . ?
C9 C8 1.410(3) . ?
C11 C12 1.369(3) . ?
C11 H11 1.00(3) . ?
C14 C13 1.371(3) . ?
C14 H14 0.93(2) . ?
C5 C6 1.374(3) . ?
C5 H5 0.97(2) . ?
C17 C18 1.384(3) . ?
C17 H17 1.02(3) . ?
C13 C12 1.388(3) . ?
C13 H13 0.97(3) . ?
C12 H12 0.98(3) . ?
C6 C7 1.387(4) . ?
C6 H6 1.00(3) . ?
C8 C7 1.375(3) . ?
C8 H8 1.01(3) . ?
C21 C20 1.382(4) . ?
C21 H21 1.03(3) . ?
C7 H7 0.97(3) . ?
C18 C19 1.374(4) . ?
C18 H18 0.99(3) . ?
C20 C19 1.382(4) . ?
C20 H20 0.91(4) . ?
C19 C22 1.519(4) . ?
C22 H22A 0.99(6) . ?
C22 H22B 1.09(5) . ?
C22 H22C 1.22(9) . ?

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 C1 106.64(16) . . ?
C2 N1 H1N 127.2(17) . . ?
C1 N1 H1N 126.1(17) . . ?
C2 N2 C3 104.42(15) . . ?
C3 C1 N1 105.59(16) . . ?
C3 C1 C15 123.55(16) . . ?
N1 C1 C15 130.75(17) . . ?
C14 C15 C10 119.91(18) . . ?
C14 C15 C1 123.66(17) . . ?
C10 C15 C1 116.42(17) . . ?
N2 C2 N1 112.64(16) . . ?
N2 C2 C16 123.20(17) . . ?
N1 C2 C16 124.16(17) . . ?
C5 C4 C9 120.24(18) . . ?
C5 C4 C3 122.45(17) . . ?
C9 C4 C3 117.29(17) . . ?
C1 C3 N2 110.68(16) . . ?
C1 C3 C4 121.38(16) . . ?
N2 C3 C4 127.87(16) . . ?
C11 C10 C15 117.29(18) . . ?
C11 C10 C9 121.97(18) . . ?
C15 C10 C9 120.73(16) . . ?
C17 C16 C21 118.8(2) . . ?
C17 C16 C2 122.43(18) . . ?
C21 C16 C2 118.59(19) . . ?
C8 C9 C4 117.46(18) . . ?
C8 C9 C10 121.96(18) . . ?
C4 C9 C10 120.58(16) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 117.4(16) . . ?
C10 C11 H11 120.8(16) . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 121.4(16) . . ?
C15 C14 H14 117.9(16) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 118.3(13) . . ?
C4 C5 H5 121.2(13) . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 116.7(19) . . ?
C18 C17 H17 123.0(19) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 119.1(16) . . ?
C12 C13 H13 120.9(16) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 117.6(18) . . ?
C13 C12 H12 121.6(18) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 119.7(14) . . ?
C7 C6 H6 120.3(14) . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 117.8(15) . . ?
C9 C8 H8 121.0(15) . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 H21 119.3(18) . . ?
C16 C21 H21 120.7(18) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 118.0(16) . . ?
C6 C7 H7 121.4(16) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 118.0(18) . . ?
C17 C18 H18 120.6(18) . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 121(2) . . ?
C21 C20 H20 118(2) . . ?
C18 C19 C20 118.2(2) . . ?
C18 C19 C22 120.3(3) . . ?
C20 C19 C22 121.5(3) . . ?
C19 C22 H22A 105(4) . . ?
C19 C22 H22B 96(2) . . ?
H22A C22 H22B 93(4) . . ?
C19 C22 H22C 102(4) . . ?
H22A C22 H22C 152(5) . . ?
H22B C22 H22C 83(4) . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_1C_298K
_database_code_depnum_ccdc_archive 'CCDC 1921678'
loop_
_audit_author_name
_audit_author_address
'Sanjay Dutta'
;Department of Chemistry, Shiv Nadar University
India
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyl)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.3758

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

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

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

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

_cell_length_a                   18.8380(7)
_cell_length_b                   9.8555(4)
_cell_length_c                   20.0216(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.797(2)
_cell_angle_gamma                90
_cell_volume                     3346.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4834
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.97

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             1372
_exptl_transmission_factor_min   0.8568
_exptl_transmission_factor_max   0.9585
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45461
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         25.681
_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             6333
_reflns_number_gt                3671
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1119P)²+0.6386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0104(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6333
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.2119
_refine_ls_wR_factor_gt          0.1729
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1B N 0.44223(13) 0.8773(3) 0.66908(13) 0.0536(6) Uani 1 1 d . . . . .
N2A N 0.39289(13) 0.5971(2) 0.64039(12) 0.0531(6) Uani 1 1 d . . . . .
N2B N 0.46410(13) 1.0928(2) 0.64848(12) 0.0560(6) Uani 1 1 d . . . . .
N1A N 0.39076(13) 0.3755(3) 0.61655(13) 0.0544(6) Uani 1 1 d . . . . .
C3B C 0.50267(15) 1.0645(3) 0.72339(15) 0.0523(7) Uani 1 1 d . . . . .
C1B C 0.49029(15) 0.9327(3) 0.73725(14) 0.0503(7) Uani 1 1 d . . . . .
C22A C 0.71574(15) 0.5370(3) 0.57881(17) 0.0637(8) Uani 1 1 d . . . . .
H22A H 0.7267 0.6308 0.5743 0.096 Uiso 1 1 calc R U . . .
H22B H 0.7079 0.4897 0.5342 0.096 Uiso 1 1 calc R U . . .
H22C H 0.7594 0.4975 0.6202 0.096 Uiso 1 1 calc R U . . .
C1A C 0.32424(15) 0.4019(3) 0.62634(14) 0.0508(7) Uani 1 1 d . . . . .
C16A C 0.50203(15) 0.5064(3) 0.61464(14) 0.0520(7) Uani 1 1 d . . . . .
C2A C 0.43006(16) 0.4958(3) 0.62497(14) 0.0522(7) Uani 1 1 d . . . . .
C3A C 0.32584(15) 0.5380(3) 0.64115(14) 0.0509(7) Uani 1 1 d . . . . .
C4B C 0.54973(16) 1.1548(3) 0.78313(15) 0.0567(7) Uani 1 1 d . . . . .
C4A C 0.26402(16) 0.6010(3) 0.65436(14) 0.0542(7) Uani 1 1 d . . . . .
C2B C 0.42894(16) 0.9775(3) 0.61800(15) 0.0538(7) Uani 1 1 d . . . . .
C15B C 0.38192(17) 0.9561(3) 0.53806(15) 0.0576(7) Uani 1 1 d . . . . .
C00G C 0.52452(15) 0.8733(3) 0.80947(14) 0.0526(7) Uani 1 1 d . . . . .
C15A C 0.26132(16) 0.3136(3) 0.61880(15) 0.0549(7) Uani 1 1 d . . . . .
C9A C 0.19979(17) 0.5172(3) 0.64707(15) 0.0574(7) Uani 1 1 d . . . . .
C9B C 0.57835(16) 1.1045(3) 0.85600(15) 0.0577(7) Uani 1 1 d . . . . .
C10B C 0.56713(16) 0.9613(3) 0.86969(15) 0.0580(7) Uani 1 1 d . . . . .
C5A C 0.26582(18) 0.7373(3) 0.67567(16) 0.0629(8) Uani 1 1 d . . . . .
H5A H 0.3083 0.7917 0.6812 0.076 Uiso 1 1 calc R U . . .
C10A C 0.19767(17) 0.3733(3) 0.62746(15) 0.0587(7) Uani 1 1 d . . . . .
C17A C 0.52457(18) 0.4019(3) 0.58207(17) 0.0635(8) Uani 1 1 d . . . . .
H17A H 0.4939 0.3238 0.5675 0.076 Uiso 1 1 calc R U . . .
C21A C 0.54866(17) 0.6207(3) 0.63542(17) 0.0648(8) Uani 1 1 d . . . . .
H21A H 0.5349 0.6926 0.6575 0.078 Uiso 1 1 calc R U . . .
C16B C 0.31662(18) 0.8699(3) 0.51065(17) 0.0689(9) Uani 1 1 d . . . . .
H16B H 0.3009 0.8271 0.5434 0.083 Uiso 1 1 calc R U . . .
C14B C 0.51827(18) 0.7340(3) 0.82300(17) 0.0630(8) Uani 1 1 d . . . . .
H14B H 0.4910 0.6758 0.7835 0.076 Uiso 1 1 calc R U . . .
C14A C 0.26007(18) 0.1760(3) 0.60203(17) 0.0645(8) Uani 1 1 d . . . . .
H14A H 0.3027 0.1378 0.5971 0.077 Uiso 1 1 calc R U . . .
C5B C 0.56681(19) 1.2870(3) 0.77030(19) 0.0729(9) Uani 1 1 d . . . . .
H5B H 0.5492 1.3183 0.7219 0.088 Uiso 1 1 calc R U . . .
C11B C 0.5996(2) 0.9060(4) 0.94148(17) 0.0723(9) Uani 1 1 d . . . . .
H11B H 0.6270 0.9622 0.9819 0.087 Uiso 1 1 calc R U . . .
C20A C 0.61521(18) 0.6300(4) 0.62401(17) 0.0699(9) Uani 1 1 d . . . . .
H20A H 0.6457 0.7083 0.6385 0.084 Uiso 1 1 calc R U . . .
C19A C 0.63805(18) 0.5254(4) 0.59150(18) 0.0701(9) Uani 1 1 d . . . . .
C6A C 0.2057(2) 0.7910(4) 0.68848(17) 0.0707(9) Uani 1 1 d . . . . .
H6A H 0.2079 0.8812 0.7029 0.085 Uiso 1 1 calc R U . . .
C13B C 0.55226(19) 0.6843(4) 0.89415(19) 0.0727(9) Uani 1 1 d . . . . .
H13B H 0.5487 0.5923 0.9027 0.087 Uiso 1 1 calc R U . . .
C18A C 0.59165(19) 0.4109(4) 0.57073(18) 0.0729(9) Uani 1 1 d . . . . .
H18A H 0.6056 0.3390 0.5488 0.087 Uiso 1 1 calc R U . . .
C8B C 0.62042(19) 1.1966(4) 0.91340(18) 0.0749(9) Uani 1 1 d . . . . .
H8B H 0.6386 1.1679 0.9623 0.090 Uiso 1 1 calc R U . . .
C20B C 0.4025(2) 1.0220(4) 0.48794(18) 0.0803(10) Uani 1 1 d . . . . .
H20B H 0.4439 1.0840 0.5049 0.096 Uiso 1 1 calc R U . . .
C8A C 0.1396(2) 0.5783(4) 0.66028(19) 0.0766(10) Uani 1 1 d . . . . .
H8A H 0.0965 0.5261 0.6554 0.092 Uiso 1 1 calc R U . . .
C12B C 0.5919(2) 0.7711(4) 0.95316(19) 0.0781(10) Uani 1 1 d . . . . .
H12B H 0.6135 0.7374 1.0013 0.094 Uiso 1 1 calc R U . . .
C13A C 0.1971(2) 0.0970(4) 0.59284(19) 0.0783(10) Uani 1 1 d . . . . .
H13A H 0.1965 0.0054 0.5813 0.094 Uiso 1 1 calc R U . . .
C11A C 0.1342(2) 0.2883(4) 0.6175(2) 0.0778(10) Uani 1 1 d . . . . .
H11A H 0.0911 0.3243 0.6224 0.093 Uiso 1 1 calc R U . . .
C7A C 0.1421(2) 0.7115(4) 0.6800(2) 0.0811(10) Uani 1 1 d . . . . .
H7A H 0.1010 0.7486 0.6878 0.097 Uiso 1 1 calc R U . . .
C7B C 0.6355(2) 1.3271(4) 0.8996(2) 0.0879(11) Uani 1 1 d . . . . .
H7B H 0.6635 1.3855 0.9388 0.105 Uiso 1 1 calc R U . . .
C6B C 0.6091(2) 1.3709(4) 0.8281(2) 0.0864(11) Uani 1 1 d . . . . .
H6B H 0.6201 1.4590 0.8187 0.104 Uiso 1 1 calc R U . . .
C17B C 0.2752(2) 0.8477(4) 0.4354(2) 0.0856(11) Uani 1 1 d . . . . .
H17B H 0.2313 0.7913 0.4178 0.103 Uiso 1 1 calc R U . . .
C18B C 0.2983(3) 0.9085(5) 0.3859(2) 0.0943(13) Uani 1 1 d . . . . .
C21B C 0.2525(2) 0.8764(5) 0.29900(16) 0.1068(15) Uani 1 1 d . . . . .
H21B H 0.2456 0.9588 0.2713 0.160 Uiso 1 1 calc R U . . .
H21C H 0.2019 0.8380 0.2883 0.160 Uiso 1 1 calc R U . . .
H21D H 0.2826 0.8131 0.2853 0.160 Uiso 1 1 calc R U . . .
C12A C 0.1341(2) 0.1543(4) 0.6008(2) 0.0900(11) Uani 1 1 d . . . . .
H12A H 0.0911 0.1006 0.5947 0.108 Uiso 1 1 calc R U . . .
C19B C 0.3618(3) 0.9961(4) 0.4127(2) 0.0965(13) Uani 1 1 d . . . . .
H19B H 0.3775 1.0382 0.3797 0.116 Uiso 1 1 calc R U . . .
H1NB H 0.4231(17) 0.787(3) 0.6568(16) 0.073(9) Uiso 1 1 d . . . . .
H1NA H 0.4135(19) 0.289(4) 0.6147(17) 0.086(11) 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
N1B C2B 1.364(3) . ?
N1B C1B 1.380(3) . ?
N1B H1NB 0.95(3) . ?
N2A C2A 1.331(3) . ?
N2A C3A 1.397(3) . ?
N2B C2B 1.323(4) . ?
N2B C3B 1.381(3) . ?
N1A C2A 1.369(4) . ?
N1A C1A 1.375(3) . ?
N1A H1NA 0.96(4) . ?
C3B C1B 1.370(4) . ?
C3B C4B 1.444(4) . ?
C1B C00G 1.427(4) . ?
C22A C19A 1.595(4) . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C1A C3A 1.371(4) . ?
C1A C15A 1.425(4) . ?
C16A C21A 1.377(4) . ?
C16A C17A 1.381(4) . ?
C16A C2A 1.461(4) . ?
C3A C4A 1.442(4) . ?
C4B C5B 1.393(4) . ?
C4B C9B 1.407(4) . ?
C4A C5A 1.405(4) . ?
C4A C9A 1.419(4) . ?
C2B C15B 1.468(4) . ?
C15B C20B 1.385(4) . ?
C15B C16B 1.396(4) . ?
C00G C14B 1.414(4) . ?
C00G C10B 1.417(4) . ?
C15A C14A 1.394(4) . ?
C15A C10A 1.413(4) . ?
C9A C8A 1.407(4) . ?
C9A C10A 1.467(4) . ?
C9B C8B 1.407(4) . ?
C9B C10B 1.471(4) . ?
C10B C11B 1.404(4) . ?
C5A C6A 1.371(4) . ?
C5A H5A 0.9300 . ?
C10A C11A 1.401(4) . ?
C17A C18A 1.381(4) . ?
C17A H17A 0.9300 . ?
C21A C20A 1.372(4) . ?
C21A H21A 0.9300 . ?
C16B C17B 1.380(4) . ?
C16B H16B 0.9300 . ?
C14B C13B 1.373(4) . ?
C14B H14B 0.9300 . ?
C14A C13A 1.363(4) . ?
C14A H14A 0.9300 . ?
C5B C6B 1.362(4) . ?
C5B H5B 0.9300 . ?
C11B C12B 1.368(5) . ?
C11B H11B 0.9300 . ?
C20A C19A 1.383(5) . ?
C20A H20A 0.9300 . ?
C19A C18A 1.376(5) . ?
C6A C7A 1.378(5) . ?
C6A H6A 0.9300 . ?
C13B C12B 1.385(5) . ?
C13B H13B 0.9300 . ?
C18A H18A 0.9300 . ?
C8B C7B 1.371(5) . ?
C8B H8B 0.9300 . ?
C20B C19B 1.385(5) . ?
C20B H20B 0.9300 . ?
C8A C7A 1.366(5) . ?
C8A H8A 0.9300 . ?
C12B H12B 0.9300 . ?
C13A C12A 1.386(5) . ?
C13A H13A 0.9300 . ?
C11A C12A 1.362(5) . ?
C11A H11A 0.9300 . ?
C7A H7A 0.9300 . ?
C7B C6B 1.366(5) . ?
C7B H7B 0.9300 . ?
C6B H6B 0.9300 . ?
C17B C18B 1.380(6) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.380(6) . ?
C18B C21B 1.602(4) . ?
C21B H21B 0.9600 . ?
C21B H21C 0.9600 . ?
C21B H21D 0.9600 . ?
C12A H12A 0.9300 . ?
C19B H19B 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
C2B N1B C1B 106.4(2) . . ?
C2B N1B H1NB 123.9(18) . . ?
C1B N1B H1NB 129.6(18) . . ?
C2A N2A C3A 105.0(2) . . ?
C2B N2B C3B 104.4(2) . . ?
C2A N1A C1A 107.3(2) . . ?
C2A N1A H1NA 123(2) . . ?
C1A N1A H1NA 129(2) . . ?
C1B C3B N2B 110.9(2) . . ?
C1B C3B C4B 120.9(2) . . ?
N2B C3B C4B 128.2(3) . . ?
C3B C1B N1B 105.7(2) . . ?
C3B C1B C00G 123.5(2) . . ?
N1B C1B C00G 130.7(3) . . ?
C19A C22A H22A 109.5 . . ?
C19A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C19A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C3A C1A N1A 106.3(2) . . ?
C3A C1A C15A 124.0(3) . . ?
N1A C1A C15A 129.6(3) . . ?
C21A C16A C17A 117.8(3) . . ?
C21A C16A C2A 121.7(3) . . ?
C17A C16A C2A 120.5(3) . . ?
N2A C2A N1A 111.5(2) . . ?
N2A C2A C16A 126.4(3) . . ?
N1A C2A C16A 122.0(3) . . ?
C1A C3A N2A 109.9(2) . . ?
C1A C3A C4A 121.2(2) . . ?
N2A C3A C4A 129.0(3) . . ?
C5B C4B C9B 120.4(3) . . ?
C5B C4B C3B 122.1(3) . . ?
C9B C4B C3B 117.5(3) . . ?
C5A C4A C9A 119.6(3) . . ?
C5A C4A C3A 123.5(3) . . ?
C9A C4A C3A 116.8(3) . . ?
N2B C2B N1B 112.6(2) . . ?
N2B C2B C15B 124.7(3) . . ?
N1B C2B C15B 122.7(3) . . ?
C20B C15B C16B 118.5(3) . . ?
C20B C15B C2B 119.7(3) . . ?
C16B C15B C2B 121.8(3) . . ?
C14B C00G C10B 119.6(3) . . ?
C14B C00G C1B 123.6(3) . . ?
C10B C00G C1B 116.7(3) . . ?
C14A C15A C10A 120.6(3) . . ?
C14A C15A C1A 123.1(3) . . ?
C10A C15A C1A 116.4(3) . . ?
C8A C9A C4A 116.9(3) . . ?
C8A C9A C10A 122.3(3) . . ?
C4A C9A C10A 120.8(3) . . ?
C8B C9B C4B 116.5(3) . . ?
C8B C9B C10B 122.8(3) . . ?
C4B C9B C10B 120.6(3) . . ?
C11B C10B C00G 117.8(3) . . ?
C11B C10B C9B 122.0(3) . . ?
C00G C10B C9B 120.2(2) . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C11A C10A C15A 116.7(3) . . ?
C11A C10A C9A 122.6(3) . . ?
C15A C10A C9A 120.7(3) . . ?
C18A C17A C16A 121.4(3) . . ?
C18A C17A H17A 119.3 . . ?
C16A C17A H17A 119.3 . . ?
C20A C21A C16A 120.9(3) . . ?
C20A C21A H21A 119.5 . . ?
C16A C21A H21A 119.5 . . ?
C17B C16B C15B 120.6(3) . . ?
C17B C16B H16B 119.7 . . ?
C15B C16B H16B 119.7 . . ?
C13B C14B C00G 120.4(3) . . ?
C13B C14B H14B 119.8 . . ?
C00G C14B H14B 119.8 . . ?
C13A C14A C15A 120.7(3) . . ?
C13A C14A H14A 119.6 . . ?
C15A C14A H14A 119.6 . . ?
C6B C5B C4B 120.5(3) . . ?
C6B C5B H5B 119.7 . . ?
C4B C5B H5B 119.7 . . ?
C12B C11B C10B 121.4(3) . . ?
C12B C11B H11B 119.3 . . ?
C10B C11B H11B 119.3 . . ?
C21A C20A C19A 121.5(3) . . ?
C21A C20A H20A 119.3 . . ?
C19A C20A H20A 119.3 . . ?
C18A C19A C20A 117.8(3) . . ?
C18A C19A C22A 121.1(3) . . ?
C20A C19A C22A 121.1(3) . . ?
C5A C6A C7A 120.1(3) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
C14B C13B C12B 119.9(3) . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C19A C18A C17A 120.6(3) . . ?
C19A C18A H18A 119.7 . . ?
C17A C18A H18A 119.7 . . ?
C7B C8B C9B 122.2(3) . . ?
C7B C8B H8B 118.9 . . ?
C9B C8B H8B 118.9 . . ?
C15B C20B C19B 120.3(4) . . ?
C15B C20B H20B 119.9 . . ?
C19B C20B H20B 119.9 . . ?
C7A C8A C9A 122.4(3) . . ?
C7A C8A H8A 118.8 . . ?
C9A C8A H8A 118.8 . . ?
C11B C12B C13B 120.8(3) . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B H12B 119.6 . . ?
C14A C13A C12A 119.4(3) . . ?
C14A C13A H13A 120.3 . . ?
C12A C13A H13A 120.3 . . ?
C12A C11A C10A 121.7(3) . . ?
C12A C11A H11A 119.1 . . ?
C10A C11A H11A 119.1 . . ?
C8A C7A C6A 120.0(3) . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C6B C7B C8B 119.7(3) . . ?
C6B C7B H7B 120.2 . . ?
C8B C7B H7B 120.2 . . ?
C5B C6B C7B 120.7(4) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C16B C17B C18B 120.7(4) . . ?
C16B C17B H17B 119.7 . . ?
C18B C17B H17B 119.7 . . ?
C17B C18B C19B 118.9(3) . . ?
C17B C18B C21B 120.3(4) . . ?
C19B C18B C21B 120.8(4) . . ?
C18B C21B H21B 109.5 . . ?
C18B C21B H21C 109.5 . . ?
H21B C21B H21C 109.5 . . ?
C18B C21B H21D 109.5 . . ?
H21B C21B H21D 109.5 . . ?
H21C C21B H21D 109.5 . . ?
C11A C12A C13A 120.8(3) . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A H12A 119.6 . . ?
C18B C19B C20B 120.9(4) . . ?
C18B C19B H19B 119.5 . . ?
C20B C19B H19B 119.5 . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_1P_373K
_database_code_depnum_ccdc_archive 'CCDC 1895792'
loop_
_audit_author_name
_audit_author_address
'Dr. Parthapratim Munshi'
;Department of Chemistry and Shiv Nadar University
India
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   14.3658(4)
_cell_length_b                   14.3658(4)
_cell_length_c                   15.8337(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3267.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    373(2)
_cell_measurement_reflns_used    6754
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.89

_exptl_crystal_description       Prismatiic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.007
_shelx_estimated_absorpt_T_max   0.007
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8156
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      373(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Xray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34858
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.382
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6653
_reflns_number_gt                5057
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.1661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6653
_refine_ls_number_parameters     561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2A N 0.37294(16) 0.99778(16) 0.91295(14) 0.0505(6) Uani 1 1 d . . . . .
N2B N 0.46279(17) 0.12231(16) 0.17000(15) 0.0519(5) Uani 1 1 d . . . . .
N1B N 0.38869(16) 0.14159(16) 0.04744(14) 0.0529(5) Uani 1 1 d . . . . .
N1A N 0.39221(16) 0.92350(15) 0.79050(13) 0.0511(5) Uani 1 1 d . . . . .
C9A C 0.35643(18) 0.7573(2) 1.00525(18) 0.0548(7) Uani 1 1 d . . . . .
C16B C 0.56071(19) 0.13900(19) 0.04099(17) 0.0529(6) Uani 1 1 d . . . . .
C15A C 0.37979(18) 0.75956(18) 0.84907(17) 0.0506(6) Uani 1 1 d . . . . .
C2B C 0.47158(19) 0.13405(18) 0.08504(17) 0.0506(6) Uani 1 1 d . . . . .
C15B C 0.22521(19) 0.13743(18) 0.10641(18) 0.0547(7) Uani 1 1 d . . . . .
C14A C 0.3860(2) 0.7121(2) 0.7718(2) 0.0617(8) Uani 1 1 d . . . . .
C10B C 0.1747(2) 0.1232(2) 0.1820(2) 0.0624(8) Uani 1 1 d . . . . .
C9B C 0.2227(2) 0.1088(2) 0.2625(2) 0.0629(7) Uani 1 1 d . . . . .
C1A C 0.38100(17) 0.85938(18) 0.85488(16) 0.0483(6) Uani 1 1 d . . . . .
C21B C 0.6451(2) 0.1197(2) 0.0809(2) 0.0617(7) Uani 1 1 d . . . . .
C16A C 0.39282(19) 1.09579(19) 0.78441(17) 0.0511(6) Uani 1 1 d . . . . .
C4B C 0.3214(2) 0.10905(19) 0.26654(17) 0.0558(7) Uani 1 1 d . . . . .
C3A C 0.36989(19) 0.90375(17) 0.93090(17) 0.0487(6) Uani 1 1 d . . . . .
C3B C 0.36911(19) 0.12257(18) 0.18841(17) 0.0506(6) Uani 1 1 d . . . . .
C4A C 0.35649(19) 0.85614(19) 1.00909(17) 0.0529(7) Uani 1 1 d . . . . .
C10A C 0.36895(19) 0.70926(18) 0.92517(18) 0.0529(7) Uani 1 1 d . . . . .
C17B C 0.5636(3) 0.1647(3) -0.04325(19) 0.0695(9) Uani 1 1 d . . . . .
C14B C 0.1783(2) 0.1525(2) 0.0300(2) 0.0665(8) Uani 1 1 d . . . . .
C2A C 0.38632(17) 1.00625(18) 0.82794(16) 0.0480(6) Uani 1 1 d . . . . .
C8A C 0.3407(2) 0.7097(2) 1.0822(2) 0.0693(8) Uani 1 1 d . . . . .
C5A C 0.3419(2) 0.9017(2) 1.08614(19) 0.0671(8) Uani 1 1 d . . . . .
C20B C 0.7281(2) 0.1271(3) 0.0367(2) 0.0700(8) Uani 1 1 d . . . . .
C8B C 0.1748(3) 0.0957(3) 0.3394(3) 0.0817(10) Uani 1 1 d . . . . .
C21A C 0.3666(2) 1.1787(2) 0.8231(2) 0.0613(7) Uani 1 1 d . . . . .
C13A C 0.3837(2) 0.6175(2) 0.7689(2) 0.0724(9) Uani 1 1 d . . . . .
C17A C 0.4269(3) 1.1009(2) 0.7024(2) 0.0706(9) Uani 1 1 d . . . . .
C18A C 0.4349(3) 1.1853(2) 0.6613(2) 0.0777(10) Uani 1 1 d . . . . .
C19A C 0.4103(2) 1.2681(2) 0.7004(2) 0.0694(8) Uani 1 1 d . . . . .
C18B C 0.6471(3) 0.1704(3) -0.0860(2) 0.0787(10) Uani 1 1 d . . . . .
C7B C 0.2212(3) 0.0832(3) 0.4142(3) 0.0904(12) Uani 1 1 d . . . . .
C20A C 0.3756(2) 1.2624(2) 0.7812(2) 0.0691(9) Uani 1 1 d . . . . .
C1B C 0.32485(19) 0.13560(18) 0.11251(17) 0.0515(6) Uani 1 1 d . . . . .
C11A C 0.3682(2) 0.6113(2) 0.9191(2) 0.0702(9) Uani 1 1 d . . . . .
C19B C 0.7313(2) 0.1528(2) -0.0469(2) 0.0715(9) Uani 1 1 d . . . . .
C13B C 0.0836(3) 0.1533(3) 0.0269(3) 0.0795(10) Uani 1 1 d . . . . .
C7A C 0.3264(3) 0.7560(3) 1.1562(2) 0.0806(10) Uani 1 1 d . . . . .
C6B C 0.3173(3) 0.0824(3) 0.4167(2) 0.0855(11) Uani 1 1 d . . . . .
C5B C 0.3670(3) 0.0955(2) 0.3437(2) 0.0702(8) Uani 1 1 d . . . . .
C22A C 0.4220(4) 1.3603(3) 0.6550(4) 0.1049(16) Uani 1 1 d . . . . .
C6A C 0.3273(3) 0.8526(3) 1.1588(2) 0.0804(10) Uani 1 1 d . . . . .
C12A C 0.3757(3) 0.5671(2) 0.8434(3) 0.0793(10) Uani 1 1 d . . . . .
C12B C 0.0330(3) 0.1387(3) 0.1003(3) 0.0889(11) Uani 1 1 d . . . . .
C11B C 0.0767(3) 0.1239(3) 0.1756(3) 0.0832(10) Uani 1 1 d . . . . .
C22B C 0.8215(4) 0.1624(5) -0.0935(4) 0.1046(16) Uani 1 1 d . . . . .
H17A H 0.443(2) 1.040(2) 0.6724(18) 0.070(9) Uiso 1 1 d . . . . .
H12A H 0.376(2) 0.498(3) 0.839(2) 0.087(10) Uiso 1 1 d . . . . .
H5A H 0.340(2) 0.975(3) 1.087(2) 0.094(11) Uiso 1 1 d . . . . .
H5B H 0.437(2) 0.095(2) 0.347(2) 0.079(10) Uiso 1 1 d . . . . .
H8B H 0.102(3) 0.092(3) 0.339(2) 0.102(12) Uiso 1 1 d . . . . .
H2NB H 0.511(2) 0.114(2) 0.209(2) 0.073(10) Uiso 1 1 d . . . . .
H13A H 0.385(3) 0.586(3) 0.714(3) 0.098(12) Uiso 1 1 d . . . . .
H21B H 0.646(2) 0.105(2) 0.1445(19) 0.066(9) Uiso 1 1 d . . . . .
H18B H 0.646(3) 0.189(3) -0.146(3) 0.111(13) Uiso 1 1 d . . . . .
H18A H 0.459(2) 1.185(2) 0.602(2) 0.093(11) Uiso 1 1 d . . . . .
H6A H 0.307(3) 0.887(3) 1.213(2) 0.104(12) Uiso 1 1 d . . . . .
H8A H 0.333(3) 0.639(3) 1.081(2) 0.099(12) Uiso 1 1 d . . . . .
H7A H 0.312(2) 0.720(3) 1.207(2) 0.091(11) Uiso 1 1 d . . . . .
H20B H 0.789(3) 0.118(2) 0.068(2) 0.090(11) Uiso 1 1 d . . . . .
H6B H 0.350(3) 0.064(3) 0.474(3) 0.103(12) Uiso 1 1 d . . . . .
H11A H 0.360(2) 0.572(2) 0.974(2) 0.085(10) Uiso 1 1 d . . . . .
H14A H 0.386(2) 0.750(2) 0.719(2) 0.073(9) Uiso 1 1 d . . . . .
H21A H 0.342(2) 1.179(2) 0.884(2) 0.079(10) Uiso 1 1 d . . . . .
H20A H 0.354(2) 1.319(2) 0.810(2) 0.080(10) Uiso 1 1 d . . . . .
H17B H 0.507(3) 0.175(2) -0.070(2) 0.084(11) Uiso 1 1 d . . . . .
H7B H 0.180(3) 0.067(3) 0.468(3) 0.117(13) Uiso 1 1 d . . . . .
H14B H 0.218(3) 0.157(2) -0.020(2) 0.088(11) Uiso 1 1 d . . . . .
H13B H 0.047(3) 0.164(3) -0.027(3) 0.106(13) Uiso 1 1 d . . . . .
H11B H 0.040(3) 0.112(3) 0.224(3) 0.113(15) Uiso 1 1 d . . . . .
H12B H -0.037(3) 0.138(3) 0.093(3) 0.111(13) Uiso 1 1 d . . . . .
H2NA H 0.372(2) 1.045(3) 0.953(2) 0.085(11) Uiso 1 1 d . . . . .
H22D H 0.842(5) 0.112(5) -0.105(4) 0.18(3) Uiso 1 1 d . . . . .
H22E H 0.812(4) 0.198(4) -0.141(4) 0.17(3) Uiso 1 1 d . . . . .
H22A H 0.438(4) 1.344(4) 0.594(4) 0.16(2) Uiso 1 1 d . . . . .
H22B H 0.474(6) 1.394(5) 0.686(5) 0.23(4) Uiso 1 1 d . . . . .
H22C H 0.377(5) 1.407(6) 0.664(5) 0.21(3) Uiso 1 1 d . . . . .
H22F H 0.873(6) 0.194(5) -0.056(5) 0.24(4) 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
N2A C2A 1.365(3) . ?
N2A C3A 1.381(3) . ?
N2A H2NA 0.94(4) . ?
N2B C2B 1.362(3) . ?
N2B C3B 1.377(4) . ?
N2B H2NB 0.94(3) . ?
N1B C2B 1.336(4) . ?
N1B C1B 1.382(4) . ?
N1A C2A 1.331(3) . ?
N1A C1A 1.383(3) . ?
C9A C8A 1.416(4) . ?
C9A C4A 1.421(4) . ?
C9A C10A 1.455(4) . ?
C16B C17B 1.385(4) . ?
C16B C21B 1.396(4) . ?
C16B C2B 1.460(4) . ?
C15A C14A 1.404(4) . ?
C15A C10A 1.414(4) . ?
C15A C1A 1.437(4) . ?
C15B C14B 1.402(4) . ?
C15B C10B 1.415(4) . ?
C15B C1B 1.435(4) . ?
C14A C13A 1.360(4) . ?
C14A H14A 1.00(3) . ?
C10B C11B 1.411(5) . ?
C10B C9B 1.464(4) . ?
C9B C8B 1.411(5) . ?
C9B C4B 1.419(4) . ?
C1A C3A 1.371(4) . ?
C21B C20B 1.387(4) . ?
C21B H21B 1.03(3) . ?
C16A C17A 1.390(4) . ?
C16A C21A 1.391(4) . ?
C16A C2A 1.462(4) . ?
C4B C5B 1.400(4) . ?
C4B C3B 1.427(4) . ?
C3A C4A 1.427(4) . ?
C3B C1B 1.373(4) . ?
C4A C5A 1.400(4) . ?
C10A C11A 1.411(4) . ?
C17B C18B 1.381(5) . ?
C17B H17B 0.94(4) . ?
C14B C13B 1.362(5) . ?
C14B H14B 0.98(4) . ?
C8A C7A 1.363(5) . ?
C8A H8A 1.02(4) . ?
C5A C6A 1.366(5) . ?
C5A H5A 1.05(4) . ?
C20B C19B 1.376(5) . ?
C20B H20B 1.01(4) . ?
C8B C7B 1.371(6) . ?
C8B H8B 1.05(4) . ?
C21A C20A 1.380(4) . ?
C21A H21A 1.03(3) . ?
C13A C12A 1.388(5) . ?
C13A H13A 0.99(4) . ?
C17A C18A 1.380(5) . ?
C17A H17A 1.02(3) . ?
C18A C19A 1.386(5) . ?
C18A H18A 1.00(4) . ?
C19A C20A 1.375(5) . ?
C19A C22A 1.517(5) . ?
C18B C19B 1.382(5) . ?
C18B H18B 0.99(4) . ?
C7B C6B 1.380(6) . ?
C7B H7B 1.06(5) . ?
C20A H20A 0.98(3) . ?
C11A C12A 1.361(5) . ?
C11A H11A 1.04(4) . ?
C19B C22B 1.498(5) . ?
C13B C12B 1.386(6) . ?
C13B H13B 1.01(4) . ?
C7A C6A 1.388(5) . ?
C7A H7A 0.97(4) . ?
C6B C5B 1.371(5) . ?
C6B H6B 1.05(4) . ?
C5B H5B 1.01(3) . ?
C22A H22A 1.02(6) . ?
C22A H22B 1.01(7) . ?
C22A H22C 0.94(8) . ?
C6A H6A 1.03(4) . ?
C12A H12A 0.99(4) . ?
C12B C11B 1.364(6) . ?
C12B H12B 1.02(4) . ?
C11B H11B 0.95(4) . ?
C22B H22D 0.81(7) . ?
C22B H22E 0.92(7) . ?
C22B H22F 1.06(8) . ?

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
C2A N2A C3A 107.1(2) . . ?
C2A N2A H2NA 128(2) . . ?
C3A N2A H2NA 125(2) . . ?
C2B N2B C3B 107.4(2) . . ?
C2B N2B H2NB 127.1(19) . . ?
C3B N2B H2NB 125.4(19) . . ?
C2B N1B C1B 104.7(2) . . ?
C2A N1A C1A 105.0(2) . . ?
C8A C9A C4A 116.5(3) . . ?
C8A C9A C10A 122.7(3) . . ?
C4A C9A C10A 120.7(2) . . ?
C17B C16B C21B 117.6(3) . . ?
C17B C16B C2B 120.0(3) . . ?
C21B C16B C2B 122.4(2) . . ?
C14A C15A C10A 120.1(2) . . ?
C14A C15A C1A 122.7(3) . . ?
C10A C15A C1A 117.2(2) . . ?
N1B C2B N2B 111.6(2) . . ?
N1B C2B C16B 124.4(2) . . ?
N2B C2B C16B 124.0(2) . . ?
C14B C15B C10B 120.4(3) . . ?
C14B C15B C1B 122.7(3) . . ?
C10B C15B C1B 116.9(3) . . ?
C13A C14A C15A 120.9(3) . . ?
C13A C14A H14A 121.3(18) . . ?
C15A C14A H14A 117.6(18) . . ?
C11B C10B C15B 116.7(3) . . ?
C11B C10B C9B 122.3(3) . . ?
C15B C10B C9B 121.0(3) . . ?
C8B C9B C4B 116.7(3) . . ?
C8B C9B C10B 122.6(3) . . ?
C4B C9B C10B 120.6(3) . . ?
C3A C1A N1A 110.5(2) . . ?
C3A C1A C15A 121.2(2) . . ?
N1A C1A C15A 128.2(2) . . ?
C20B C21B C16B 120.2(3) . . ?
C20B C21B H21B 119.7(17) . . ?
C16B C21B H21B 120.0(17) . . ?
C17A C16A C21A 117.5(3) . . ?
C17A C16A C2A 120.6(3) . . ?
C21A C16A C2A 121.9(3) . . ?
C5B C4B C9B 120.4(3) . . ?
C5B C4B C3B 123.4(3) . . ?
C9B C4B C3B 116.2(3) . . ?
C1A C3A N2A 105.7(2) . . ?
C1A C3A C4A 123.7(2) . . ?
N2A C3A C4A 130.6(2) . . ?
C1B C3B N2B 105.5(2) . . ?
C1B C3B C4B 123.7(3) . . ?
N2B C3B C4B 130.7(3) . . ?
C5A C4A C9A 120.3(3) . . ?
C5A C4A C3A 123.5(3) . . ?
C9A C4A C3A 116.2(2) . . ?
C11A C10A C15A 116.9(3) . . ?
C11A C10A C9A 122.1(3) . . ?
C15A C10A C9A 120.9(2) . . ?
C18B C17B C16B 120.9(3) . . ?
C18B C17B H17B 122(2) . . ?
C16B C17B H17B 117(2) . . ?
C13B C14B C15B 120.8(4) . . ?
C13B C14B H14B 124(2) . . ?
C15B C14B H14B 115(2) . . ?
N1A C2A N2A 111.6(2) . . ?
N1A C2A C16A 124.9(2) . . ?
N2A C2A C16A 123.5(2) . . ?
C7A C8A C9A 121.9(3) . . ?
C7A C8A H8A 119(2) . . ?
C9A C8A H8A 119(2) . . ?
C6A C5A C4A 121.0(3) . . ?
C6A C5A H5A 120(2) . . ?
C4A C5A H5A 119(2) . . ?
C19B C20B C21B 122.4(3) . . ?
C19B C20B H20B 118(2) . . ?
C21B C20B H20B 119(2) . . ?
C7B C8B C9B 121.6(4) . . ?
C7B C8B H8B 119(2) . . ?
C9B C8B H8B 119(2) . . ?
C20A C21A C16A 120.6(3) . . ?
C20A C21A H21A 118.6(18) . . ?
C16A C21A H21A 120.8(18) . . ?
C14A C13A C12A 119.6(3) . . ?
C14A C13A H13A 120(2) . . ?
C12A C13A H13A 121(2) . . ?
C18A C17A C16A 121.1(3) . . ?
C18A C17A H17A 120.9(17) . . ?
C16A C17A H17A 117.9(17) . . ?
C17A C18A C19A 121.4(3) . . ?
C17A C18A H18A 118(2) . . ?
C19A C18A H18A 121(2) . . ?
C20A C19A C18A 117.2(3) . . ?
C20A C19A C22A 122.2(4) . . ?
C18A C19A C22A 120.6(4) . . ?
C17B C18B C19B 122.0(3) . . ?
C17B C18B H18B 118(2) . . ?
C19B C18B H18B 120(2) . . ?
C8B C7B C6B 120.8(4) . . ?
C8B C7B H7B 116(2) . . ?
C6B C7B H7B 122(2) . . ?
C19A C20A C21A 122.2(3) . . ?
C19A C20A H20A 120(2) . . ?
C21A C20A H20A 118(2) . . ?
C3B C1B N1B 110.7(2) . . ?
C3B C1B C15B 121.6(3) . . ?
N1B C1B C15B 127.6(2) . . ?
C12A C11A C10A 121.6(3) . . ?
C12A C11A H11A 119.6(19) . . ?
C10A C11A H11A 118.8(19) . . ?
C20B C19B C18B 116.8(3) . . ?
C20B C19B C22B 121.9(4) . . ?
C18B C19B C22B 121.3(4) . . ?
C14B C13B C12B 119.5(4) . . ?
C14B C13B H13B 124(2) . . ?
C12B C13B H13B 117(2) . . ?
C8A C7A C6A 120.8(3) . . ?
C8A C7A H7A 118(2) . . ?
C6A C7A H7A 121(2) . . ?
C5B C6B C7B 119.7(4) . . ?
C5B C6B H6B 122(2) . . ?
C7B C6B H6B 118(2) . . ?
C6B C5B C4B 120.7(3) . . ?
C6B C5B H5B 118(2) . . ?
C4B C5B H5B 121(2) . . ?
C19A C22A H22A 106(3) . . ?
C19A C22A H22B 105(4) . . ?
H22A C22A H22B 114(5) . . ?
C19A C22A H22C 118(5) . . ?
H22A C22A H22C 118(6) . . ?
H22B C22A H22C 95(6) . . ?
C5A C6A C7A 119.5(3) . . ?
C5A C6A H6A 120(2) . . ?
C7A C6A H6A 120(2) . . ?
C11A C12A C13A 120.8(3) . . ?
C11A C12A H12A 122(2) . . ?
C13A C12A H12A 117(2) . . ?
C11B C12B C13B 121.0(4) . . ?
C11B C12B H12B 124(2) . . ?
C13B C12B H12B 115(2) . . ?
C12B C11B C10B 121.5(4) . . ?
C12B C11B H11B 118(3) . . ?
C10B C11B H11B 120(3) . . ?
C19B C22B H22D 110(5) . . ?
C19B C22B H22E 109(4) . . ?
H22D C22B H22E 112(6) . . ?
C19B C22B H22F 112(4) . . ?
H22D C22B H22F 105(6) . . ?
H22E C22B H22F 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
C1B N1B C2B N2B 0.9(3) . . . . ?
C1B N1B C2B C16B -178.3(2) . . . . ?
C3B N2B C2B N1B -0.2(3) . . . . ?
C3B N2B C2B C16B 179.0(2) . . . . ?
C17B C16B C2B N1B 8.7(4) . . . . ?
C21B C16B C2B N1B -172.1(3) . . . . ?
C17B C16B C2B N2B -170.4(3) . . . . ?
C21B C16B C2B N2B 8.8(4) . . . . ?
C10A C15A C14A C13A -1.5(4) . . . . ?
C1A C15A C14A C13A -179.4(3) . . . . ?
C14B C15B C10B C11B 0.8(4) . . . . ?
C1B C15B C10B C11B -179.3(3) . . . . ?
C14B C15B C10B C9B -179.0(3) . . . . ?
C1B C15B C10B C9B 0.9(4) . . . . ?
C11B C10B C9B C8B -0.7(5) . . . . ?
C15B C10B C9B C8B 179.1(3) . . . . ?
C11B C10B C9B C4B -179.7(3) . . . . ?
C15B C10B C9B C4B 0.1(4) . . . . ?
C2A N1A C1A C3A -0.9(3) . . . . ?
C2A N1A C1A C15A 178.8(3) . . . . ?
C14A C15A C1A C3A 176.5(3) . . . . ?
C10A C15A C1A C3A -1.5(4) . . . . ?
C14A C15A C1A N1A -3.2(4) . . . . ?
C10A C15A C1A N1A 178.8(2) . . . . ?
C17B C16B C21B C20B 0.4(5) . . . . ?
C2B C16B C21B C20B -178.8(3) . . . . ?
C8B C9B C4B C5B 0.8(4) . . . . ?
C10B C9B C4B C5B 179.9(3) . . . . ?
C8B C9B C4B C3B -179.9(3) . . . . ?
C10B C9B C4B C3B -0.9(4) . . . . ?
N1A C1A C3A N2A 0.9(3) . . . . ?
C15A C1A C3A N2A -178.9(2) . . . . ?
N1A C1A C3A C4A 179.8(3) . . . . ?
C15A C1A C3A C4A 0.0(4) . . . . ?
C2A N2A C3A C1A -0.5(3) . . . . ?
C2A N2A C3A C4A -179.3(3) . . . . ?
C2B N2B C3B C1B -0.6(3) . . . . ?
C2B N2B C3B C4B 177.0(3) . . . . ?
C5B C4B C3B C1B 179.8(3) . . . . ?
C9B C4B C3B C1B 0.5(4) . . . . ?
C5B C4B C3B N2B 2.5(5) . . . . ?
C9B C4B C3B N2B -176.7(3) . . . . ?
C8A C9A C4A C5A 0.3(4) . . . . ?
C10A C9A C4A C5A 178.3(3) . . . . ?
C8A C9A C4A C3A -178.3(3) . . . . ?
C10A C9A C4A C3A -0.3(4) . . . . ?
C1A C3A C4A C5A -177.7(3) . . . . ?
N2A C3A C4A C5A 1.0(5) . . . . ?
C1A C3A C4A C9A 0.9(4) . . . . ?
N2A C3A C4A C9A 179.5(3) . . . . ?
C14A C15A C10A C11A 2.2(4) . . . . ?
C1A C15A C10A C11A -179.7(3) . . . . ?
C14A C15A C10A C9A -176.0(3) . . . . ?
C1A C15A C10A C9A 2.0(4) . . . . ?
C8A C9A C10A C11A -1.4(4) . . . . ?
C4A C9A C10A C11A -179.3(3) . . . . ?
C8A C9A C10A C15A 176.7(3) . . . . ?
C4A C9A C10A C15A -1.2(4) . . . . ?
C21B C16B C17B C18B 0.4(5) . . . . ?
C2B C16B C17B C18B 179.6(3) . . . . ?
C10B C15B C14B C13B -0.3(4) . . . . ?
C1B C15B C14B C13B 179.7(3) . . . . ?
C1A N1A C2A N2A 0.7(3) . . . . ?
C1A N1A C2A C16A -179.1(2) . . . . ?
C3A N2A C2A N1A -0.1(3) . . . . ?
C3A N2A C2A C16A 179.6(2) . . . . ?
C17A C16A C2A N1A -14.8(4) . . . . ?
C21A C16A C2A N1A 166.0(3) . . . . ?
C17A C16A C2A N2A 165.4(3) . . . . ?
C21A C16A C2A N2A -13.7(4) . . . . ?
C4A C9A C8A C7A -0.1(5) . . . . ?
C10A C9A C8A C7A -178.1(3) . . . . ?
C9A C4A C5A C6A 0.0(5) . . . . ?
C3A C4A C5A C6A 178.5(3) . . . . ?
C16B C21B C20B C19B -0.3(5) . . . . ?
C4B C9B C8B C7B -0.4(5) . . . . ?
C10B C9B C8B C7B -179.4(4) . . . . ?
C17A C16A C21A C20A -0.7(5) . . . . ?
C2A C16A C21A C20A 178.5(3) . . . . ?
C15A C14A C13A C12A -0.3(5) . . . . ?
C21A C16A C17A C18A 0.4(5) . . . . ?
C2A C16A C17A C18A -178.8(3) . . . . ?
C16A C17A C18A C19A 0.7(6) . . . . ?
C17A C18A C19A C20A -1.5(5) . . . . ?
C17A C18A C19A C22A 178.4(4) . . . . ?
C16B C17B C18B C19B -1.3(6) . . . . ?
C9B C8B C7B C6B -0.5(6) . . . . ?
C18A C19A C20A C21A 1.2(5) . . . . ?
C22A C19A C20A C21A -178.7(4) . . . . ?
C16A C21A C20A C19A -0.1(5) . . . . ?
N2B C3B C1B N1B 1.2(3) . . . . ?
C4B C3B C1B N1B -176.7(2) . . . . ?
N2B C3B C1B C15B 178.4(2) . . . . ?
C4B C3B C1B C15B 0.6(4) . . . . ?
C2B N1B C1B C3B -1.3(3) . . . . ?
C2B N1B C1B C15B -178.3(2) . . . . ?
C14B C15B C1B C3B 178.7(3) . . . . ?
C10B C15B C1B C3B -1.3(4) . . . . ?
C14B C15B C1B N1B -4.6(4) . . . . ?
C10B C15B C1B N1B 175.5(3) . . . . ?
C15A C10A C11A C12A -1.3(5) . . . . ?
C9A C10A C11A C12A 176.9(3) . . . . ?
C21B C20B C19B C18B -0.5(5) . . . . ?
C21B C20B C19B C22B 178.7(4) . . . . ?
C17B C18B C19B C20B 1.4(6) . . . . ?
C17B C18B C19B C22B -177.9(4) . . . . ?
C15B C14B C13B C12B -0.2(5) . . . . ?
C9A C8A C7A C6A -0.4(6) . . . . ?
C8B C7B C6B C5B 0.9(6) . . . . ?
C7B C6B C5B C4B -0.4(6) . . . . ?
C9B C4B C5B C6B -0.4(5) . . . . ?
C3B C4B C5B C6B -179.7(3) . . . . ?
C4A C5A C6A C7A -0.4(6) . . . . ?
C8A C7A C6A C5A 0.6(6) . . . . ?
C10A C11A C12A C13A -0.5(5) . . . . ?
C14A C13A C12A C11A 1.3(5) . . . . ?
C14B C13B C12B C11B 0.3(6) . . . . ?
C13B C12B C11B C10B 0.2(6) . . . . ?
C15B C10B C11B C12B -0.7(5) . . . . ?
C9B C10B C11B C12B 179.1(3) . . . . ?

_refine_diff_density_max         0.097
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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_1P_473K
_database_code_depnum_ccdc_archive 'CCDC 1921679'
loop_
_audit_author_name
_audit_author_address
'Sanjay Dutta'
;Department of Chemistry, Shiv Nadar University
India
;
_audit_update_record             
;
2019-06-07 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   14.510(15)
_cell_length_b                   14.510(15)
_cell_length_c                   15.944(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3357(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    473(2)
_cell_measurement_reflns_used    1468
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      20.89

_exptl_crystal_description       Prismatiic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.5673
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      473(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Xray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8388
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         26.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             5826
_reflns_number_gt                2574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.710
_reflns_Friedel_fraction_full    0.735

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1874P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.069(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5826
_refine_ls_number_parameters     436
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_ref         0.3456
_refine_ls_wR_factor_gt          0.2436
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.8727(5) 0.4964(6) 0.6312(5) 0.075(2) Uani 1 1 d . . . . .
H001 H 0.8676 0.5410 0.6665 0.090 Uiso 1 1 calc R U . . .
N002 N 0.0364(6) 0.3776(6) 0.3876(5) 0.079(2) Uani 1 1 d . . . . .
H002 H -0.0081 0.3833 0.4229 0.095 Uiso 1 1 calc R U . . .
N003 N 0.8917(6) 0.4224(5) 0.5095(5) 0.074(2) Uani 1 1 d . . . . .
C004 C 0.8855(7) 0.5047(7) 0.5458(6) 0.069(2) Uani 1 1 d . . . . .
C3 C 0.8579(6) 0.2572(8) 0.7227(7) 0.079(3) Uani 1 1 d . . . . .
N006 N 0.1103(6) 0.3601(6) 0.2651(5) 0.078(2) Uani 1 1 d . . . . .
C007 C 0.0277(7) 0.3660(7) 0.3022(6) 0.074(3) Uani 1 1 d . . . . .
C2 C 0.1769(8) 0.3903(7) 0.4831(6) 0.080(3) Uani 1 1 d . . . . .
C4 C 0.8299(11) 0.2554(11) 0.8733(8) 0.122(5) Uani 1 1 d . . . . .
H4 H 0.8229 0.2222 0.9228 0.146 Uiso 1 1 calc R U . . .
C7 C 0.8931(7) 0.5939(7) 0.5033(6) 0.070(2) Uani 1 1 d . . . . .
C00B C 0.8697(7) 0.4035(7) 0.6497(6) 0.069(2) Uani 1 1 d . . . . .
C5 C 0.9081(9) 0.7655(9) 0.4196(8) 0.101(4) Uani 1 1 d . . . . .
C1 C 0.3194(9) 0.3508(8) 0.2492(7) 0.098(4) Uani 1 1 d . . . . .
H1 H 0.2862 0.3426 0.1999 0.118 Uiso 1 1 calc R U . . .
C00E C 0.8573(7) 0.3553(7) 0.7267(6) 0.076(3) Uani 1 1 d . . . . .
C00F C 0.8413(8) 0.2108(9) 0.8000(8) 0.099(4) Uani 1 1 d . . . . .
H00F H 0.8382 0.1468 0.7998 0.119 Uiso 1 1 calc R U . . .
C00G C 0.8806(6) 0.2588(7) 0.5676(6) 0.072(3) Uani 1 1 d . . . . .
C00H C 0.2719(7) 0.3643(7) 0.3236(6) 0.076(3) Uani 1 1 d . . . . .
C00I C 0.2744(15) 0.4137(10) 0.6324(10) 0.133(5) Uani 1 1 d . . . . .
H00I H 0.3069 0.4204 0.6823 0.159 Uiso 1 1 calc R U . . .
C00J C 0.2757(8) 0.3893(7) 0.4800(7) 0.088(3) Uani 1 1 d . . . . .
C00K C -0.0646(8) 0.3389(9) 0.1758(7) 0.098(4) Uani 1 1 d . . . . .
H00K H -0.0102 0.3271 0.1469 0.118 Uiso 1 1 calc R U . . .
C00L C -0.2266(8) 0.3739(9) 0.2549(8) 0.100(4) Uani 1 1 d . . . . .
H00L H -0.2809 0.3868 0.2835 0.120 Uiso 1 1 calc R U . . .
C00M C -0.0605(7) 0.3623(7) 0.2586(6) 0.078(3) Uani 1 1 d . . . . .
C00N C 0.8439(8) 0.4002(8) 0.8032(6) 0.090(3) Uani 1 1 d . . . . .
H00N H 0.8455 0.4642 0.8050 0.108 Uiso 1 1 calc R U . . .
C00O C -0.2325(9) 0.3499(9) 0.1723(8) 0.103(4) Uani 1 1 d . . . . .
C00P C 0.8696(7) 0.2086(7) 0.6424(6) 0.074(3) Uani 1 1 d . . . . .
C00Q C 0.8744(9) 0.7599(8) 0.5006(8) 0.099(4) Uani 1 1 d . . . . .
H00Q H 0.8565 0.8135 0.5281 0.119 Uiso 1 1 calc R U . . .
C00R C 0.1735(7) 0.3653(7) 0.3311(6) 0.076(3) Uani 1 1 d . . . . .
C00S C 0.8670(8) 0.6768(7) 0.5413(6) 0.084(3) Uani 1 1 d . . . . .
H00S H 0.8439 0.6755 0.5957 0.101 Uiso 1 1 calc R U . . .
C00T C 0.8857(8) 0.2130(8) 0.4914(7) 0.088(3) Uani 1 1 d . . . . .
H00T H 0.8900 0.2465 0.4418 0.106 Uiso 1 1 calc R U . . .
C00U C 0.8811(7) 0.3581(7) 0.5739(6) 0.072(3) Uani 1 1 d . . . . .
C00V C 0.9321(10) 0.6840(10) 0.3833(8) 0.112(4) Uani 1 1 d . . . . .
H00V H 0.9545 0.6851 0.3286 0.135 Uiso 1 1 calc R U . . .
C00W C 0.4627(10) 0.3632(10) 0.3194(10) 0.117(4) Uani 1 1 d . . . . .
H00W H 0.5268 0.3630 0.3176 0.141 Uiso 1 1 calc R U . . .
C00X C 0.1286(7) 0.3785(7) 0.4065(6) 0.070(2) Uani 1 1 d . . . . .
C00Y C 0.1812(13) 0.4148(10) 0.6335(8) 0.117(5) Uani 1 1 d . . . . .
H00Y H 0.1500 0.4235 0.6838 0.140 Uiso 1 1 calc R U . . .
C00Z C 0.8286(12) 0.3524(11) 0.8749(7) 0.124(5) Uani 1 1 d . . . . .
H00Z H 0.8173 0.3835 0.9249 0.149 Uiso 1 1 calc R U . . .
C010 C -0.1483(10) 0.3325(10) 0.1335(8) 0.114(4) Uani 1 1 d . . . . .
H010 H -0.1480 0.3160 0.0771 0.137 Uiso 1 1 calc R U . . .
C011 C 0.1322(9) 0.4029(9) 0.5600(7) 0.093(3) Uani 1 1 d . . . . .
H011 H 0.0681 0.4032 0.5617 0.112 Uiso 1 1 calc R U . . .
C012 C 0.4140(10) 0.3492(9) 0.2459(9) 0.113(4) Uani 1 1 d . . . . .
H012 H 0.4445 0.3389 0.1955 0.136 Uiso 1 1 calc R U . . .
C6 C 0.9251(10) 0.6001(9) 0.4228(7) 0.104(4) Uani 1 1 d . . . . .
H6 H 0.9424 0.5469 0.3944 0.125 Uiso 1 1 calc R U . . .
C014 C 0.3226(7) 0.3768(8) 0.3991(7) 0.085(3) Uani 1 1 d . . . . .
C015 C 0.8846(9) 0.1183(9) 0.4890(8) 0.107(4) Uani 1 1 d . . . . .
H015 H 0.8895 0.0883 0.4377 0.128 Uiso 1 1 calc R U . . .
C016 C 0.8695(9) 0.1113(8) 0.6370(8) 0.098(4) Uani 1 1 d . . . . .
H016 H 0.8648 0.0768 0.6859 0.117 Uiso 1 1 calc R U . . .
C017 C 0.3220(10) 0.4028(10) 0.5577(9) 0.113(4) Uani 1 1 d . . . . .
H017 H 0.3860 0.4043 0.5583 0.135 Uiso 1 1 calc R U . . .
C018 C -0.1443(8) 0.3800(8) 0.2982(6) 0.090(3) Uani 1 1 d . . . . .
H018 H -0.1449 0.3961 0.3546 0.108 Uiso 1 1 calc R U . . .
C019 C 0.8761(10) 0.0669(9) 0.5621(10) 0.114(4) Uani 1 1 d . . . . .
H019 H 0.8750 0.0028 0.5599 0.137 Uiso 1 1 calc R U . . .
C01A C 0.4197(9) 0.3773(10) 0.3942(9) 0.112(4) Uani 1 1 d . . . . .
H01A H 0.4545 0.3874 0.4423 0.134 Uiso 1 1 calc R U . . .
C01B C 0.9191(12) 0.8571(10) 0.3742(11) 0.147(6) Uani 1 1 d . . . . .
H01B H 0.9767 0.8848 0.3897 0.221 Uiso 1 1 calc R U . . .
H01C H 0.8694 0.8975 0.3895 0.221 Uiso 1 1 calc R U . . .
H01D H 0.9180 0.8469 0.3147 0.221 Uiso 1 1 calc R U . . .
C01C C -0.3208(10) 0.3405(12) 0.1248(9) 0.142(6) Uani 1 1 d . . . . .
H01E H -0.3654 0.3092 0.1590 0.213 Uiso 1 1 calc R U . . .
H01F H -0.3102 0.3057 0.0746 0.213 Uiso 1 1 calc R U . . .
H01G H -0.3436 0.4006 0.1104 0.213 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 C004 1.379(12) . ?
N001 C00B 1.380(12) . ?
N001 H001 0.8600 . ?
N002 C00X 1.371(12) . ?
N002 C007 1.379(12) . ?
N002 H002 0.8600 . ?
N003 C004 1.331(12) . ?
N003 C00U 1.395(12) . ?
C004 C7 1.466(13) . ?
C3 C00F 1.424(15) . ?
C3 C00E 1.424(15) . ?
C3 C00P 1.471(15) . ?
N006 C007 1.339(13) . ?
N006 C00R 1.397(13) . ?
C007 C00M 1.458(14) . ?
C2 C011 1.399(15) . ?
C2 C00X 1.419(14) . ?
C2 C00J 1.434(15) . ?
C4 C00F 1.346(17) . ?
C4 C00Z 1.407(19) . ?
C4 H4 0.9300 . ?
C7 C6 1.368(13) . ?
C7 C00S 1.399(14) . ?
C00B C00U 1.386(13) . ?
C00B C00E 1.424(14) . ?
C5 C00V 1.363(17) . ?
C5 C00Q 1.383(16) . ?
C5 C01B 1.523(17) . ?
C1 C012 1.374(17) . ?
C1 C00H 1.386(14) . ?
C1 H1 0.9300 . ?
C00E C00N 1.396(14) . ?
C00F H00F 0.9300 . ?
C00G C00T 1.386(14) . ?
C00G C00P 1.408(14) . ?
C00G C00U 1.444(14) . ?
C00H C014 1.422(15) . ?
C00H C00R 1.432(14) . ?
C00I C00Y 1.35(2) . ?
C00I C017 1.39(2) . ?
C00I H00I 0.9300 . ?
C00J C017 1.422(16) . ?
C00J C014 1.470(16) . ?
C00K C00M 1.364(13) . ?
C00K C010 1.392(17) . ?
C00K H00K 0.9300 . ?
C00L C00O 1.364(16) . ?
C00L C018 1.382(15) . ?
C00L H00L 0.9300 . ?
C00M C018 1.393(14) . ?
C00N C00Z 1.356(16) . ?
C00N H00N 0.9300 . ?
C00O C010 1.392(18) . ?
C00O C01C 1.495(17) . ?
C00P C016 1.414(14) . ?
C00Q C00S 1.374(15) . ?
C00Q H00Q 0.9300 . ?
C00R C00X 1.380(13) . ?
C00S H00S 0.9300 . ?
C00T C015 1.375(15) . ?
C00T H00T 0.9300 . ?
C00V C6 1.373(16) . ?
C00V H00V 0.9300 . ?
C00W C01A 1.362(19) . ?
C00W C012 1.38(2) . ?
C00W H00W 0.9300 . ?
C00Y C011 1.381(16) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C6 H6 0.9300 . ?
C014 C01A 1.410(16) . ?
C015 C019 1.390(18) . ?
C015 H015 0.9300 . ?
C016 C019 1.360(18) . ?
C016 H016 0.9300 . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9600 . ?
C01B H01C 0.9600 . ?
C01B H01D 0.9600 . ?
C01C H01E 0.9600 . ?
C01C H01F 0.9600 . ?
C01C H01G 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
C004 N001 C00B 107.5(8) . . ?
C004 N001 H001 126.3 . . ?
C00B N001 H001 126.3 . . ?
C00X N002 C007 107.8(8) . . ?
C00X N002 H002 126.1 . . ?
C007 N002 H002 126.1 . . ?
C004 N003 C00U 105.7(7) . . ?
N003 C004 N001 111.2(8) . . ?
N003 C004 C7 125.8(8) . . ?
N001 C004 C7 123.0(9) . . ?
C00F C3 C00E 115.6(10) . . ?
C00F C3 C00P 123.0(10) . . ?
C00E C3 C00P 121.2(9) . . ?
C007 N006 C00R 104.6(8) . . ?
N006 C007 N002 111.2(9) . . ?
N006 C007 C00M 125.0(8) . . ?
N002 C007 C00M 123.8(9) . . ?
C011 C2 C00X 122.8(10) . . ?
C011 C2 C00J 119.7(9) . . ?
C00X C2 C00J 117.6(9) . . ?
C00F C4 C00Z 119.9(11) . . ?
C00F C4 H4 120.1 . . ?
C00Z C4 H4 120.1 . . ?
C6 C7 C00S 116.2(10) . . ?
C6 C7 C004 121.2(10) . . ?
C00S C7 C004 122.6(9) . . ?
N001 C00B C00U 105.9(8) . . ?
N001 C00B C00E 131.9(9) . . ?
C00U C00B C00E 122.2(9) . . ?
C00V C5 C00Q 115.9(11) . . ?
C00V C5 C01B 121.9(12) . . ?
C00Q C5 C01B 122.2(13) . . ?
C012 C1 C00H 122.2(13) . . ?
C012 C1 H1 118.9 . . ?
C00H C1 H1 118.9 . . ?
C00N C00E C00B 122.8(10) . . ?
C00N C00E C3 120.4(9) . . ?
C00B C00E C3 116.8(9) . . ?
C4 C00F C3 123.0(12) . . ?
C4 C00F H00F 118.5 . . ?
C3 C00F H00F 118.5 . . ?
C00T C00G C00P 120.0(9) . . ?
C00T C00G C00U 122.7(10) . . ?
C00P C00G C00U 117.2(8) . . ?
C1 C00H C014 119.0(10) . . ?
C1 C00H C00R 124.6(10) . . ?
C014 C00H C00R 116.4(9) . . ?
C00Y C00I C017 120.6(14) . . ?
C00Y C00I H00I 119.7 . . ?
C017 C00I H00I 119.7 . . ?
C017 C00J C2 116.1(11) . . ?
C017 C00J C014 124.2(12) . . ?
C2 C00J C014 119.7(10) . . ?
C00M C00K C010 121.5(11) . . ?
C00M C00K H00K 119.2 . . ?
C010 C00K H00K 119.2 . . ?
C00O C00L C018 123.6(12) . . ?
C00O C00L H00L 118.2 . . ?
C018 C00L H00L 118.2 . . ?
C00K C00M C018 116.5(10) . . ?
C00K C00M C007 120.6(10) . . ?
C018 C00M C007 122.9(9) . . ?
C00Z C00N C00E 121.4(11) . . ?
C00Z C00N H00N 119.3 . . ?
C00E C00N H00N 119.3 . . ?
C00L C00O C010 114.8(11) . . ?
C00L C00O C01C 124.4(14) . . ?
C010 C00O C01C 120.7(13) . . ?
C00G C00P C016 117.7(10) . . ?
C00G C00P C3 120.2(9) . . ?
C016 C00P C3 122.2(10) . . ?
C00S C00Q C5 121.3(11) . . ?
C00S C00Q H00Q 119.3 . . ?
C5 C00Q H00Q 119.3 . . ?
C00X C00R N006 110.6(9) . . ?
C00X C00R C00H 123.0(9) . . ?
N006 C00R C00H 126.2(9) . . ?
C00Q C00S C7 122.0(10) . . ?
C00Q C00S H00S 119.0 . . ?
C7 C00S H00S 119.0 . . ?
C015 C00T C00G 120.2(11) . . ?
C015 C00T H00T 119.9 . . ?
C00G C00T H00T 119.9 . . ?
C00B C00U N003 109.8(9) . . ?
C00B C00U C00G 122.3(9) . . ?
N003 C00U C00G 127.9(8) . . ?
C5 C00V C6 123.7(11) . . ?
C5 C00V H00V 118.2 . . ?
C6 C00V H00V 118.2 . . ?
C01A C00W C012 121.9(13) . . ?
C01A C00W H00W 119.0 . . ?
C012 C00W H00W 119.0 . . ?
N002 C00X C00R 105.6(9) . . ?
N002 C00X C2 132.2(9) . . ?
C00R C00X C2 122.2(10) . . ?
C00I C00Y C011 120.2(14) . . ?
C00I C00Y H00Y 119.9 . . ?
C011 C00Y H00Y 119.9 . . ?
C00N C00Z C4 119.6(12) . . ?
C00N C00Z H00Z 120.2 . . ?
C4 C00Z H00Z 120.2 . . ?
C00O C010 C00K 122.6(11) . . ?
C00O C010 H010 118.7 . . ?
C00K C010 H010 118.7 . . ?
C00Y C011 C2 121.4(12) . . ?
C00Y C011 H011 119.3 . . ?
C2 C011 H011 119.3 . . ?
C1 C012 C00W 118.4(12) . . ?
C1 C012 H012 120.8 . . ?
C00W C012 H012 120.8 . . ?
C7 C6 C00V 121.0(11) . . ?
C7 C6 H6 119.5 . . ?
C00V C6 H6 119.5 . . ?
C01A C014 C00H 118.1(11) . . ?
C01A C014 C00J 120.7(11) . . ?
C00H C014 C00J 121.2(10) . . ?
C00T C015 C019 121.0(11) . . ?
C00T C015 H015 119.5 . . ?
C019 C015 H015 119.5 . . ?
C019 C016 C00P 121.9(11) . . ?
C019 C016 H016 119.1 . . ?
C00P C016 H016 119.1 . . ?
C00I C017 C00J 122.0(14) . . ?
C00I C017 H017 119.0 . . ?
C00J C017 H017 119.0 . . ?
C00L C018 C00M 121.0(10) . . ?
C00L C018 H018 119.5 . . ?
C00M C018 H018 119.5 . . ?
C016 C019 C015 119.2(11) . . ?
C016 C019 H019 120.4 . . ?
C015 C019 H019 120.4 . . ?
C00W C01A C014 120.4(12) . . ?
C00W C01A H01A 119.8 . . ?
C014 C01A H01A 119.8 . . ?
C5 C01B H01B 109.5 . . ?
C5 C01B H01C 109.5 . . ?
H01B C01B H01C 109.5 . . ?
C5 C01B H01D 109.5 . . ?
H01B C01B H01D 109.5 . . ?
H01C C01B H01D 109.5 . . ?
C00O C01C H01E 109.5 . . ?
C00O C01C H01F 109.5 . . ?
H01E C01C H01F 109.5 . . ?
C00O C01C H01G 109.5 . . ?
H01E C01C H01G 109.5 . . ?
H01F C01C H01G 109.5 . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.195


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_1P_298K
_database_code_depnum_ccdc_archive 'CCDC 1895791'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Department of Chemistry and Shiv Nadar University
India
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            2-(p-tolyll)-1H-phenanthro[9,10-d]imidazole
_chemical_melting_point          563
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   14.3222(6)
_cell_length_b                   14.3222(6)
_cell_length_c                   15.7591(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3232.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6754
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.89

_exptl_crystal_description       Prismatiic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8156
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Xray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21337
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_full        25.242
_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 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6589
_reflns_number_gt                5118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.994

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.1314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6589
_refine_ls_number_parameters     561
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1B N 0.35734(16) 0.11212(16) 0.50188(14) 0.0400(5) Uani 1 1 d . . . . .
N2B N 0.37773(16) 0.03789(17) 0.37884(15) 0.0395(5) Uani 1 1 d . . . . .
N1A N 0.50135(16) 0.12698(16) 0.63612(15) 0.0389(5) Uani 1 1 d . . . . .
N2A N 0.57600(15) 0.10718(16) 0.75898(14) 0.0395(5) Uani 1 1 d . . . . .
C2A C 0.49258(18) 0.11291(17) 0.72143(17) 0.0365(6) Uani 1 1 d . . . . .
C15A C 0.64355(19) 0.1440(2) 0.53963(18) 0.0397(6) Uani 1 1 d . . . . .
C9A C 0.79090(18) 0.13120(19) 0.62401(18) 0.0405(6) Uani 1 1 d . . . . .
C3B C 0.37730(18) 0.13202(19) 0.36054(18) 0.0391(6) Uani 1 1 d . . . . .
C16A C 0.40288(19) 0.10653(19) 0.76535(18) 0.0388(6) Uani 1 1 d . . . . .
C16B C 0.36033(19) -0.06065(19) 0.50819(18) 0.0405(6) Uani 1 1 d . . . . .
C2B C 0.36545(18) 0.02913(19) 0.46417(17) 0.0384(6) Uani 1 1 d . . . . .
C8A C 0.8894(2) 0.1319(2) 0.6300(2) 0.0538(8) Uani 1 1 d . . . . .
C10B C 0.3765(2) 0.3272(2) 0.3670(2) 0.0481(7) Uani 1 1 d . . . . .
C1A C 0.59571(18) 0.13012(19) 0.61797(18) 0.0378(6) Uani 1 1 d . . . . .
C14A C 0.5979(2) 0.1590(2) 0.4622(2) 0.0516(8) Uani 1 1 d . . . . .
C15B C 0.36171(18) 0.27645(19) 0.44268(18) 0.0420(7) Uani 1 1 d . . . . .
C10A C 0.7428(2) 0.14405(19) 0.54350(19) 0.0420(7) Uani 1 1 d . . . . .
C5A C 0.7876(2) 0.1138(2) 0.7778(2) 0.0475(7) Uani 1 1 d . . . . .
C4A C 0.74016(18) 0.11991(18) 0.70033(18) 0.0387(6) Uani 1 1 d . . . . .
C1B C 0.36369(18) 0.17627(19) 0.43676(18) 0.0395(6) Uani 1 1 d . . . . .
C3A C 0.64028(18) 0.11867(18) 0.69419(17) 0.0373(6) Uani 1 1 d . . . . .
C17A C 0.3199(2) 0.1337(2) 0.7270(2) 0.0470(7) Uani 1 1 d . . . . .
C4B C 0.39143(19) 0.1797(2) 0.28187(18) 0.0426(7) Uani 1 1 d . . . . .
C9B C 0.3914(2) 0.2790(2) 0.2858(2) 0.0481(7) Uani 1 1 d . . . . .
C5B C 0.4055(2) 0.1342(2) 0.2046(2) 0.0532(8) Uani 1 1 d . . . . .
C20A C 0.3135(2) 0.0637(2) 0.8890(2) 0.0586(9) Uani 1 1 d . . . . .
C21A C 0.3979(2) 0.0722(2) 0.8479(2) 0.0532(8) Uani 1 1 d . . . . .
C17B C 0.3336(2) -0.0634(2) 0.59284(19) 0.0526(8) Uani 1 1 d . . . . .
C8B C 0.4055(3) 0.3271(3) 0.2090(2) 0.0618(9) Uani 1 1 d . . . . .
C21B C 0.3803(2) -0.1454(2) 0.4681(2) 0.0469(7) Uani 1 1 d . . . . .
C20B C 0.3730(2) -0.2285(2) 0.5126(2) 0.0532(8) Uani 1 1 d . . . . .
C19A C 0.2304(2) 0.0886(2) 0.8502(2) 0.0539(8) Uani 1 1 d . . . . .
C11B C 0.3757(3) 0.4256(2) 0.3732(3) 0.0643(10) Uani 1 1 d . . . . .
C13A C 0.6473(3) 0.1742(3) 0.3892(2) 0.0603(9) Uani 1 1 d . . . . .
C7A C 0.9337(2) 0.1246(3) 0.7063(3) 0.0613(9) Uani 1 1 d . . . . .
C14B C 0.3458(2) 0.3234(2) 0.5192(2) 0.0510(8) Uani 1 1 d . . . . .
C11A C 0.7906(2) 0.1604(2) 0.4666(2) 0.0518(8) Uani 1 1 d . . . . .
C12A C 0.7444(3) 0.1750(3) 0.3919(2) 0.0611(9) Uani 1 1 d . . . . .
C18A C 0.2355(2) 0.1247(2) 0.7689(2) 0.0523(8) Uani 1 1 d . . . . .
C22A C 0.1379(3) 0.0765(4) 0.8953(4) 0.0803(13) Uani 1 1 d . . . . .
C12B C 0.3603(3) 0.4695(3) 0.4487(3) 0.0682(10) Uani 1 1 d . . . . .
C6A C 0.8830(2) 0.1166(2) 0.7809(2) 0.0550(8) Uani 1 1 d . . . . .
C6B C 0.4191(3) 0.1843(3) 0.1311(2) 0.0649(10) Uani 1 1 d . . . . .
C7B C 0.4187(3) 0.2806(3) 0.1338(3) 0.0682(10) Uani 1 1 d . . . . .
C18B C 0.3274(3) -0.1466(3) 0.6359(2) 0.0590(9) Uani 1 1 d . . . . .
C13B C 0.3447(3) 0.4186(2) 0.5224(2) 0.0606(9) Uani 1 1 d . . . . .
C22B C 0.3360(4) -0.3216(3) 0.6437(4) 0.0792(13) Uani 1 1 d . . . . .
C19B C 0.3460(2) -0.2314(2) 0.5969(2) 0.0542(8) Uani 1 1 d . . . . .
H14A H 0.526(2) 0.162(2) 0.459(2) 0.067(10) Uiso 1 1 d . . . . .
H12A H 0.779(2) 0.192(2) 0.342(2) 0.055(8) Uiso 1 1 d . . . . .
H7A H 1.003(3) 0.125(2) 0.709(2) 0.067(10) Uiso 1 1 d . . . . .
H11A H 0.859(3) 0.167(2) 0.465(2) 0.073(11) Uiso 1 1 d . . . . .
H6A H 0.915(3) 0.112(2) 0.839(2) 0.071(10) Uiso 1 1 d . . . . .
H8A H 0.926(2) 0.141(2) 0.575(2) 0.064(10) Uiso 1 1 d . . . . .
H13A H 0.613(2) 0.193(2) 0.335(2) 0.075(11) Uiso 1 1 d . . . . .
H20A H 0.313(2) 0.038(2) 0.948(2) 0.060(9) Uiso 1 1 d . . . . .
H21A H 0.459(2) 0.051(2) 0.8759(18) 0.057(9) Uiso 1 1 d . . . . .
H18A H 0.179(2) 0.145(2) 0.7418(19) 0.054(9) Uiso 1 1 d . . . . .
H17A H 0.319(2) 0.159(2) 0.6687(19) 0.048(8) Uiso 1 1 d . . . . .
H18B H 0.308(3) -0.147(3) 0.700(3) 0.089(12) Uiso 1 1 d . . . . .
H21B H 0.396(2) -0.145(2) 0.407(2) 0.051(9) Uiso 1 1 d . . . . .
H5B H 0.406(2) 0.065(2) 0.200(2) 0.065(10) Uiso 1 1 d . . . . .
H6B H 0.436(3) 0.152(3) 0.075(3) 0.078(11) Uiso 1 1 d . . . . .
H17B H 0.321(2) -0.006(3) 0.621(2) 0.072(11) Uiso 1 1 d . . . . .
H20B H 0.384(2) -0.289(3) 0.482(2) 0.077(11) Uiso 1 1 d . . . . .
H7B H 0.432(3) 0.318(3) 0.081(3) 0.084(12) Uiso 1 1 d . . . . .
H8B H 0.410(2) 0.396(3) 0.208(2) 0.075(11) Uiso 1 1 d . . . . .
H13B H 0.334(3) 0.454(3) 0.575(3) 0.081(12) Uiso 1 1 d . . . . .
H5A H 0.751(2) 0.113(2) 0.829(2) 0.059(9) Uiso 1 1 d . . . . .
H22D H 0.293(4) -0.368(5) 0.612(4) 0.17(3) Uiso 1 1 d . . . . .
H2NB H 0.386(2) -0.010(2) 0.339(2) 0.067(11) Uiso 1 1 d . . . . .
H14B H 0.338(2) 0.285(2) 0.569(2) 0.070(11) Uiso 1 1 d . . . . .
H11B H 0.389(2) 0.462(3) 0.324(3) 0.079(12) Uiso 1 1 d . . . . .
H12B H 0.359(2) 0.540(3) 0.456(3) 0.085(12) Uiso 1 1 d . . . . .
H1NA H 0.455(2) 0.129(2) 0.594(2) 0.057(9) Uiso 1 1 d . . . . .
H22A H 0.149(3) 0.061(3) 0.952(4) 0.119(19) Uiso 1 1 d . . . . .
H22E H 0.306(4) -0.312(4) 0.695(4) 0.14(2) Uiso 1 1 d . . . . .
H22B H 0.094(5) 0.123(4) 0.885(4) 0.16(2) Uiso 1 1 d . . . . .
H22F H 0.385(4) -0.350(4) 0.648(4) 0.14(3) Uiso 1 1 d . . . . .
H22C H 0.102(4) 0.024(5) 0.867(4) 0.18(3) 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
N1B C2B 1.334(4) . ?
N1B C1B 1.380(4) . ?
N2B C2B 1.362(4) . ?
N2B C3B 1.379(4) . ?
N2B H2NB 0.94(4) . ?
N1A C2A 1.365(4) . ?
N1A C1A 1.382(3) . ?
N1A H1NA 0.94(3) . ?
N2A C2A 1.336(3) . ?
N2A C3A 1.385(3) . ?
C2A C16A 1.462(4) . ?
C15A C14A 1.401(4) . ?
C15A C10A 1.423(4) . ?
C15A C1A 1.426(4) . ?
C9A C8A 1.414(4) . ?
C9A C4A 1.414(4) . ?
C9A C10A 1.455(4) . ?
C3B C1B 1.372(4) . ?
C3B C4B 1.430(4) . ?
C16A C17A 1.389(4) . ?
C16A C21A 1.392(4) . ?
C16B C17B 1.388(4) . ?
C16B C21B 1.397(4) . ?
C16B C2B 1.463(4) . ?
C8A C7A 1.364(5) . ?
C8A H8A 1.01(4) . ?
C10B C11B 1.412(4) . ?
C10B C15B 1.413(4) . ?
C10B C9B 1.469(4) . ?
C1A C3A 1.370(4) . ?
C14A C13A 1.368(4) . ?
C14A H14A 1.03(3) . ?
C15B C14B 1.399(4) . ?
C15B C1B 1.438(4) . ?
C10A C11A 1.412(4) . ?
C5A C6A 1.367(4) . ?
C5A C4A 1.400(4) . ?
C5A H5A 0.96(3) . ?
C4A C3A 1.434(4) . ?
C17A C18A 1.385(4) . ?
C17A H17A 0.98(3) . ?
C4B C5B 1.396(4) . ?
C4B C9B 1.424(4) . ?
C9B C8B 1.406(4) . ?
C5B C6B 1.376(5) . ?
C5B H5B 0.99(3) . ?
C20A C21A 1.376(4) . ?
C20A C19A 1.384(5) . ?
C20A H20A 0.99(3) . ?
C21A H21A 1.03(3) . ?
C17B C18B 1.374(5) . ?
C17B H17B 0.95(4) . ?
C8B C7B 1.372(5) . ?
C8B H8B 0.99(4) . ?
C21B C20B 1.386(4) . ?
C21B H21B 1.00(3) . ?
C20B C19B 1.383(4) . ?
C20B H20B 1.00(4) . ?
C19A C18A 1.383(5) . ?
C19A C22A 1.514(5) . ?
C11B C12B 1.365(6) . ?
C11B H11B 0.95(4) . ?
C13A C12A 1.392(5) . ?
C13A H13A 1.03(4) . ?
C7A C6A 1.386(5) . ?
C7A H7A 0.99(4) . ?
C14B C13B 1.364(5) . ?
C14B H14B 0.96(4) . ?
C11A C12A 1.366(5) . ?
C11A H11A 0.99(4) . ?
C12A H12A 0.96(3) . ?
C18A H18A 0.96(3) . ?
C22A H22A 0.94(6) . ?
C22A H22B 0.94(6) . ?
C22A H22C 1.02(6) . ?
C12B C13B 1.389(6) . ?
C12B H12B 1.02(4) . ?
C6A H6A 1.02(4) . ?
C6B C7B 1.380(5) . ?
C6B H6B 1.03(4) . ?
C7B H7B 1.01(4) . ?
C18B C19B 1.387(5) . ?
C18B H18B 1.05(4) . ?
C13B H13B 0.98(4) . ?
C22B C19B 1.495(5) . ?
C22B H22D 1.03(7) . ?
C22B H22E 0.94(6) . ?
C22B H22F 0.82(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
C2B N1B C1B 104.8(2) . . ?
C2B N2B C3B 107.2(2) . . ?
C2B N2B H2NB 128(2) . . ?
C3B N2B H2NB 125(2) . . ?
C2A N1A C1A 107.4(2) . . ?
C2A N1A H1NA 129.3(19) . . ?
C1A N1A H1NA 123.1(19) . . ?
C2A N2A C3A 105.1(2) . . ?
N2A C2A N1A 111.3(2) . . ?
N2A C2A C16A 124.9(2) . . ?
N1A C2A C16A 123.8(2) . . ?
C14A C15A C10A 120.3(3) . . ?
C14A C15A C1A 123.4(2) . . ?
C10A C15A C1A 116.3(3) . . ?
C8A C9A C4A 117.2(3) . . ?
C8A C9A C10A 122.0(3) . . ?
C4A C9A C10A 120.8(2) . . ?
C1B C3B N2B 105.6(2) . . ?
C1B C3B C4B 124.0(2) . . ?
N2B C3B C4B 130.4(3) . . ?
C17A C16A C21A 117.5(3) . . ?
C17A C16A C2A 121.9(3) . . ?
C21A C16A C2A 120.6(3) . . ?
C17B C16B C21B 117.8(3) . . ?
C17B C16B C2B 119.6(3) . . ?
C21B C16B C2B 122.6(3) . . ?
N1B C2B N2B 111.7(2) . . ?
N1B C2B C16B 124.6(2) . . ?
N2B C2B C16B 123.8(2) . . ?
C7A C8A C9A 121.5(3) . . ?
C7A C8A H8A 121.3(19) . . ?
C9A C8A H8A 117.1(19) . . ?
C11B C10B C15B 117.0(3) . . ?
C11B C10B C9B 122.0(3) . . ?
C15B C10B C9B 121.1(2) . . ?
C3A C1A N1A 105.7(2) . . ?
C3A C1A C15A 123.5(2) . . ?
N1A C1A C15A 130.8(2) . . ?
C13A C14A C15A 121.0(3) . . ?
C13A C14A H14A 118(2) . . ?
C15A C14A H14A 121(2) . . ?
C14B C15B C10B 120.3(3) . . ?
C14B C15B C1B 122.6(3) . . ?
C10B C15B C1B 117.1(3) . . ?
C11A C10A C15A 116.6(3) . . ?
C11A C10A C9A 122.7(3) . . ?
C15A C10A C9A 120.7(2) . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A H5A 121.1(19) . . ?
C4A C5A H5A 117.7(19) . . ?
C5A C4A C9A 120.0(2) . . ?
C5A C4A C3A 122.8(3) . . ?
C9A C4A C3A 117.2(2) . . ?
C3B C1B N1B 110.7(2) . . ?
C3B C1B C15B 121.4(3) . . ?
N1B C1B C15B 127.9(3) . . ?
C1A C3A N2A 110.5(2) . . ?
C1A C3A C4A 121.5(2) . . ?
N2A C3A C4A 128.0(2) . . ?
C18A C17A C16A 120.9(3) . . ?
C18A C17A H17A 118.1(17) . . ?
C16A C17A H17A 121.0(17) . . ?
C5B C4B C9B 120.3(3) . . ?
C5B C4B C3B 123.7(3) . . ?
C9B C4B C3B 116.1(3) . . ?
C8B C9B C4B 116.9(3) . . ?
C8B C9B C10B 122.7(3) . . ?
C4B C9B C10B 120.4(3) . . ?
C6B C5B C4B 120.7(3) . . ?
C6B C5B H5B 117(2) . . ?
C4B C5B H5B 122(2) . . ?
C21A C20A C19A 121.6(3) . . ?
C21A C20A H20A 118.1(19) . . ?
C19A C20A H20A 120.3(19) . . ?
C20A C21A C16A 121.0(3) . . ?
C20A C21A H21A 121.4(17) . . ?
C16A C21A H21A 117.5(17) . . ?
C18B C17B C16B 121.1(3) . . ?
C18B C17B H17B 121(2) . . ?
C16B C17B H17B 118(2) . . ?
C7B C8B C9B 121.7(3) . . ?
C7B C8B H8B 117(2) . . ?
C9B C8B H8B 121(2) . . ?
C20B C21B C16B 120.1(3) . . ?
C20B C21B H21B 121.0(18) . . ?
C16B C21B H21B 118.8(18) . . ?
C19B C20B C21B 122.2(3) . . ?
C19B C20B H20B 119(2) . . ?
C21B C20B H20B 119(2) . . ?
C18A C19A C20A 117.4(3) . . ?
C18A C19A C22A 121.6(4) . . ?
C20A C19A C22A 121.0(4) . . ?
C12B C11B C10B 121.5(4) . . ?
C12B C11B H11B 119(2) . . ?
C10B C11B H11B 119(2) . . ?
C14A C13A C12A 119.6(3) . . ?
C14A C13A H13A 119.8(19) . . ?
C12A C13A H13A 120.2(19) . . ?
C8A C7A C6A 120.7(3) . . ?
C8A C7A H7A 120(2) . . ?
C6A C7A H7A 119(2) . . ?
C13B C14B C15B 121.0(3) . . ?
C13B C14B H14B 123(2) . . ?
C15B C14B H14B 116(2) . . ?
C12A C11A C10A 122.1(3) . . ?
C12A C11A H11A 116(2) . . ?
C10A C11A H11A 121(2) . . ?
C11A C12A C13A 120.5(3) . . ?
C11A C12A H12A 119.3(19) . . ?
C13A C12A H12A 119.9(19) . . ?
C19A C18A C17A 121.5(3) . . ?
C19A C18A H18A 118.6(18) . . ?
C17A C18A H18A 119.9(18) . . ?
C19A C22A H22A 109(3) . . ?
C19A C22A H22B 116(4) . . ?
H22A C22A H22B 117(5) . . ?
C19A C22A H22C 109(4) . . ?
H22A C22A H22C 110(5) . . ?
H22B C22A H22C 97(5) . . ?
C11B C12B C13B 120.9(3) . . ?
C11B C12B H12B 124(2) . . ?
C13B C12B H12B 115(2) . . ?
C5A C6A C7A 119.7(3) . . ?
C5A C6A H6A 119(2) . . ?
C7A C6A H6A 122(2) . . ?
C5B C6B C7B 119.7(4) . . ?
C5B C6B H6B 121(2) . . ?
C7B C6B H6B 119(2) . . ?
C8B C7B C6B 120.7(3) . . ?
C8B C7B H7B 118(2) . . ?
C6B C7B H7B 121(2) . . ?
C17B C18B C19B 121.9(3) . . ?
C17B C18B H18B 120(2) . . ?
C19B C18B H18B 118(2) . . ?
C14B C13B C12B 119.4(3) . . ?
C14B C13B H13B 123(2) . . ?
C12B C13B H13B 117(2) . . ?
C19B C22B H22D 112(3) . . ?
C19B C22B H22E 110(3) . . ?
H22D C22B H22E 104(5) . . ?
C19B C22B H22F 113(4) . . ?
H22D C22B H22F 103(5) . . ?
H22E C22B H22F 114(5) . . ?
C20B C19B C18B 116.9(3) . . ?
C20B C19B C22B 121.7(4) . . ?
C18B C19B C22B 121.4(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
C3A N2A C2A N1A 0.3(3) . . . . ?
C3A N2A C2A C16A -178.8(2) . . . . ?
C1A N1A C2A N2A 0.2(3) . . . . ?
C1A N1A C2A C16A 179.3(2) . . . . ?
C2B N2B C3B C1B -0.6(3) . . . . ?
C2B N2B C3B C4B 176.9(3) . . . . ?
N2A C2A C16A C17A 165.1(3) . . . . ?
N1A C2A C16A C17A -13.9(4) . . . . ?
N2A C2A C16A C21A -15.1(4) . . . . ?
N1A C2A C16A C21A 165.9(3) . . . . ?
C1B N1B C2B N2B 0.8(3) . . . . ?
C1B N1B C2B C16B -178.3(2) . . . . ?
C3B N2B C2B N1B -0.1(3) . . . . ?
C3B N2B C2B C16B 178.9(2) . . . . ?
C17B C16B C2B N1B 8.7(4) . . . . ?
C21B C16B C2B N1B -172.1(3) . . . . ?
C17B C16B C2B N2B -170.2(3) . . . . ?
C21B C16B C2B N2B 9.0(4) . . . . ?
C4A C9A C8A C7A -1.7(4) . . . . ?
C10A C9A C8A C7A 176.6(3) . . . . ?
C2A N1A C1A C3A -0.6(3) . . . . ?
C2A N1A C1A C15A -179.3(3) . . . . ?
C14A C15A C1A C3A -177.6(3) . . . . ?
C10A C15A C1A C3A 1.0(4) . . . . ?
C14A C15A C1A N1A 0.8(5) . . . . ?
C10A C15A C1A N1A 179.5(3) . . . . ?
C10A C15A C14A C13A -0.2(5) . . . . ?
C1A C15A C14A C13A 178.4(3) . . . . ?
C11B C10B C15B C14B 0.9(4) . . . . ?
C9B C10B C15B C14B -178.7(3) . . . . ?
C11B C10B C15B C1B -179.2(3) . . . . ?
C9B C10B C15B C1B 1.2(4) . . . . ?
C14A C15A C10A C11A 0.4(4) . . . . ?
C1A C15A C10A C11A -178.3(3) . . . . ?
C14A C15A C10A C9A 178.2(3) . . . . ?
C1A C15A C10A C9A -0.5(4) . . . . ?
C8A C9A C10A C11A -1.6(4) . . . . ?
C4A C9A C10A C11A 176.6(3) . . . . ?
C8A C9A C10A C15A -179.3(3) . . . . ?
C4A C9A C10A C15A -1.0(4) . . . . ?
C6A C5A C4A C9A -1.4(4) . . . . ?
C6A C5A C4A C3A -179.1(3) . . . . ?
C8A C9A C4A C5A 2.5(4) . . . . ?
C10A C9A C4A C5A -175.8(3) . . . . ?
C8A C9A C4A C3A -179.7(3) . . . . ?
C10A C9A C4A C3A 2.0(4) . . . . ?
N2B C3B C1B N1B 1.1(3) . . . . ?
C4B C3B C1B N1B -176.6(2) . . . . ?
N2B C3B C1B C15B 178.4(2) . . . . ?
C4B C3B C1B C15B 0.7(4) . . . . ?
C2B N1B C1B C3B -1.1(3) . . . . ?
C2B N1B C1B C15B -178.2(2) . . . . ?
C14B C15B C1B C3B 178.5(3) . . . . ?
C10B C15B C1B C3B -1.4(4) . . . . ?
C14B C15B C1B N1B -4.8(4) . . . . ?
C10B C15B C1B N1B 175.4(3) . . . . ?
N1A C1A C3A N2A 0.9(3) . . . . ?
C15A C1A C3A N2A 179.6(3) . . . . ?
N1A C1A C3A C4A -178.8(2) . . . . ?
C15A C1A C3A C4A 0.0(4) . . . . ?
C2A N2A C3A C1A -0.7(3) . . . . ?
C2A N2A C3A C4A 178.9(3) . . . . ?
C5A C4A C3A C1A 176.2(3) . . . . ?
C9A C4A C3A C1A -1.5(4) . . . . ?
C5A C4A C3A N2A -3.4(4) . . . . ?
C9A C4A C3A N2A 178.9(2) . . . . ?
C21A C16A C17A C18A -1.5(4) . . . . ?
C2A C16A C17A C18A 178.2(3) . . . . ?
C1B C3B C4B C5B 179.8(3) . . . . ?
N2B C3B C4B C5B 2.7(5) . . . . ?
C1B C3B C4B C9B 0.3(4) . . . . ?
N2B C3B C4B C9B -176.7(3) . . . . ?
C5B C4B C9B C8B 0.3(4) . . . . ?
C3B C4B C9B C8B 179.8(3) . . . . ?
C5B C4B C9B C10B 180.0(3) . . . . ?
C3B C4B C9B C10B -0.5(4) . . . . ?
C11B C10B C9B C8B -0.1(5) . . . . ?
C15B C10B C9B C8B 179.4(3) . . . . ?
C11B C10B C9B C4B -179.8(3) . . . . ?
C15B C10B C9B C4B -0.3(4) . . . . ?
C9B C4B C5B C6B -0.3(5) . . . . ?
C3B C4B C5B C6B -179.7(3) . . . . ?
C19A C20A C21A C16A 0.1(5) . . . . ?
C17A C16A C21A C20A 1.4(5) . . . . ?
C2A C16A C21A C20A -178.3(3) . . . . ?
C21B C16B C17B C18B 0.3(5) . . . . ?
C2B C16B C17B C18B 179.5(3) . . . . ?
C4B C9B C8B C7B 0.1(5) . . . . ?
C10B C9B C8B C7B -179.7(3) . . . . ?
C17B C16B C21B C20B 0.1(4) . . . . ?
C2B C16B C21B C20B -179.1(3) . . . . ?
C16B C21B C20B C19B 0.1(5) . . . . ?
C21A C20A C19A C18A -1.6(5) . . . . ?
C21A C20A C19A C22A 178.4(4) . . . . ?
C15B C10B C11B C12B -0.7(5) . . . . ?
C9B C10B C11B C12B 178.9(3) . . . . ?
C15A C14A C13A C12A -0.1(5) . . . . ?
C9A C8A C7A C6A -0.3(5) . . . . ?
C10B C15B C14B C13B -0.3(4) . . . . ?
C1B C15B C14B C13B 179.8(3) . . . . ?
C15A C10A C11A C12A -0.3(4) . . . . ?
C9A C10A C11A C12A -178.1(3) . . . . ?
C10A C11A C12A C13A 0.0(5) . . . . ?
C14A C13A C12A C11A 0.2(6) . . . . ?
C20A C19A C18A C17A 1.5(5) . . . . ?
C22A C19A C18A C17A -178.5(4) . . . . ?
C16A C17A C18A C19A 0.1(5) . . . . ?
C10B C11B C12B C13B -0.1(6) . . . . ?
C4A C5A C6A C7A -0.7(5) . . . . ?
C8A C7A C6A C5A 1.5(5) . . . . ?
C4B C5B C6B C7B -0.1(6) . . . . ?
C9B C8B C7B C6B -0.4(6) . . . . ?
C5B C6B C7B C8B 0.4(6) . . . . ?
C16B C17B C18B C19B -1.1(5) . . . . ?
C15B C14B C13B C12B -0.5(5) . . . . ?
C11B C12B C13B C14B 0.7(6) . . . . ?
C21B C20B C19B C18B -0.8(5) . . . . ?
C21B C20B C19B C22B 178.5(4) . . . . ?
C17B C18B C19B C20B 1.3(5) . . . . ?
C17B C18B C19B C22B -178.0(4) . . . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028

