# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_av90m
_database_code_depnum_ccdc_archive 'CCDC 1059104'
_audit_update_record             
;
2015-04-13 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 9-(pyrimidin-2-yl)-1-(p-tolyl)-9H-carbazole 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N3'
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n  '
_symmetry_space_group_name_Hall  ' -P 2yn'
loop_
_symmetry_equiv_pos_as_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                   9.5942(6)
_cell_length_b                   11.3101(7)
_cell_length_c                   16.4330(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.6930(10)
_cell_angle_gamma                90.00
_cell_volume                     1771.01(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9274
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16640
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3128
_reflns_number_gt                2784
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0643P)²+0.2227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3128
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.32828(13) 0.41313(12) 0.26062(8) 0.0577(3) Uani 1 1 d . . .
H2 H 0.3768 0.3440 0.2762 0.069 Uiso 1 1 calc R . .
C3 C 0.40019(14) 0.51772(13) 0.26449(9) 0.0634(4) Uani 1 1 d . . .
H3 H 0.4963 0.5207 0.2808 0.076 Uiso 1 1 calc R . .
C4 C 0.32441(14) 0.61770(12) 0.24335(9) 0.0605(3) Uani 1 1 d . . .
H4 H 0.3706 0.6901 0.2458 0.073 Uiso 1 1 calc R . .
C5 C -0.07839(12) 0.54799(10) 0.11561(7) 0.0484(3) Uani 1 1 d . . .
C1 C 0.12889(12) 0.50883(9) 0.21678(7) 0.0427(3) Uani 1 1 d . . .
C6 C -0.02728(14) 0.63093(12) 0.06433(8) 0.0588(3) Uani 1 1 d . . .
H6 H 0.0597 0.6666 0.0776 0.071 Uiso 1 1 calc R . .
C7 C -0.11130(17) 0.65818(14) -0.00726(9) 0.0727(4) Uani 1 1 d . . .
H7 H -0.0799 0.7135 -0.0428 0.087 Uiso 1 1 calc R . .
C8 C -0.24104(18) 0.60540(16) -0.02758(9) 0.0780(5) Uani 1 1 d . . .
H8 H -0.2955 0.6262 -0.0760 0.094 Uiso 1 1 calc R . .
C9 C -0.28986(15) 0.52251(14) 0.02336(9) 0.0689(4) Uani 1 1 d . . .
H9 H -0.3766 0.4867 0.0094 0.083 Uiso 1 1 calc R . .
C10 C -0.20811(13) 0.49291(11) 0.09592(8) 0.0536(3) Uani 1 1 d . . .
C11 C -0.22782(12) 0.41182(11) 0.16173(8) 0.0528(3) Uani 1 1 d . . .
C12 C -0.11006(12) 0.42173(10) 0.22027(7) 0.0465(3) Uani 1 1 d . . .
C16 C -0.33637(14) 0.33487(14) 0.17510(9) 0.0674(4) Uani 1 1 d . . .
H16 H -0.4148 0.3272 0.1365 0.081 Uiso 1 1 calc R . .
C15 C -0.32519(16) 0.27090(14) 0.24626(9) 0.0713(4) Uani 1 1 d . . .
H15 H -0.3948 0.2167 0.2549 0.086 Uiso 1 1 calc R . .
C14 C -0.21171(15) 0.28583(12) 0.30541(9) 0.0630(3) Uani 1 1 d . . .
H14 H -0.2087 0.2422 0.3535 0.076 Uiso 1 1 calc R . .
C13 C -0.10158(13) 0.36336(10) 0.29622(7) 0.0508(3) Uani 1 1 d . . .
C17 C 0.00873(13) 0.38549(10) 0.36510(7) 0.0508(3) Uani 1 1 d . . .
C22 C 0.07330(15) 0.29323(12) 0.41111(8) 0.0613(3) Uani 1 1 d . . .
H22 H 0.0456 0.2158 0.3990 0.074 Uiso 1 1 calc R . .
C21 C 0.17752(16) 0.31463(14) 0.47430(8) 0.0695(4) Uani 1 1 d . . .
H21 H 0.2199 0.2512 0.5035 0.083 Uiso 1 1 calc R . .
C20 C 0.22067(15) 0.42839(15) 0.49527(9) 0.0681(4) Uani 1 1 d . . .
C19 C 0.15432(15) 0.52043(13) 0.45099(8) 0.0641(4) Uani 1 1 d . . .
H19 H 0.1806 0.5978 0.4644 0.077 Uiso 1 1 calc R . .
C18 C 0.05030(14) 0.50012(11) 0.38756(8) 0.0549(3) Uani 1 1 d . . .
H18 H 0.0070 0.5639 0.3592 0.066 Uiso 1 1 calc R . .
C23 C 0.33246(19) 0.4506(2) 0.56579(11) 0.0981(6) Uani 1 1 d . . .
H23A H 0.2937 0.4394 0.6165 0.147 Uiso 1 1 calc R . .
H23B H 0.3663 0.5302 0.5629 0.147 Uiso 1 1 calc R . .
H23C H 0.4087 0.3964 0.5629 0.147 Uiso 1 1 calc R . .
N1 N -0.01651(10) 0.50379(8) 0.19145(6) 0.0449(2) Uani 1 1 d . . .
N2 N 0.19142(10) 0.40634(8) 0.23538(6) 0.0482(3) Uani 1 1 d . . .
N3 N 0.18623(11) 0.61531(8) 0.21933(7) 0.0540(3) Uani 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
C2 N2 1.3324(15) . ?
C2 C3 1.3672(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3672(19) . ?
C3 H3 0.9300 . ?
C4 N3 1.3387(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.3881(18) . ?
C5 C10 1.3956(18) . ?
C5 N1 1.4083(15) . ?
C1 N3 1.3227(14) . ?
C1 N2 1.3246(14) . ?
C1 N1 1.4096(15) . ?
C6 C7 1.3811(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.3896(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.4471(19) . ?
C11 C16 1.3942(18) . ?
C11 C12 1.4004(17) . ?
C12 C13 1.4058(17) . ?
C12 N1 1.4108(14) . ?
C16 C15 1.369(2) . ?
C16 H16 0.9300 . ?
C15 C14 1.383(2) . ?
C15 H15 0.9300 . ?
C14 C13 1.3948(18) . ?
C14 H14 0.9300 . ?
C13 C17 1.4781(18) . ?
C17 C22 1.3910(18) . ?
C17 C18 1.3935(17) . ?
C22 C21 1.3765(19) . ?
C22 H22 0.9300 . ?
C21 C20 1.383(2) . ?
C21 H21 0.9300 . ?
C20 C19 1.382(2) . ?
C20 C23 1.506(2) . ?
C19 C18 1.3759(19) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
N2 C2 C3 122.55(11) . . ?
N2 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 116.96(12) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
N3 C4 C3 122.50(11) . . ?
N3 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C6 C5 C10 121.97(12) . . ?
C6 C5 N1 129.40(12) . . ?
C10 C5 N1 108.62(10) . . ?
N3 C1 N2 127.88(11) . . ?
N3 C1 N1 116.09(10) . . ?
N2 C1 N1 116.02(9) . . ?
C7 C6 C5 117.09(13) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C8 121.86(14) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 120.47(13) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.24(14) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 119.36(13) . . ?
C9 C10 C11 133.16(13) . . ?
C5 C10 C11 107.47(11) . . ?
C16 C11 C12 119.96(12) . . ?
C16 C11 C10 132.73(12) . . ?
C12 C11 C10 107.31(10) . . ?
C11 C12 C13 122.07(11) . . ?
C11 C12 N1 108.41(10) . . ?
C13 C12 N1 129.32(11) . . ?
C15 C16 C11 118.62(13) . . ?
C15 C16 H16 120.7 . . ?
C11 C16 H16 120.7 . . ?
C16 C15 C14 120.86(13) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C14 C13 123.03(13) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C13 C12 115.16(12) . . ?
C14 C13 C17 120.49(11) . . ?
C12 C13 C17 124.24(11) . . ?
C22 C17 C18 117.29(12) . . ?
C22 C17 C13 121.53(11) . . ?
C18 C17 C13 121.17(11) . . ?
C21 C22 C17 121.10(13) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C22 C21 C20 121.44(13) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C19 C20 C21 117.61(13) . . ?
C19 C20 C23 121.51(16) . . ?
C21 C20 C23 120.85(16) . . ?
C18 C19 C20 121.47(14) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C18 C17 121.06(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 N1 C1 123.20(10) . . ?
C5 N1 C12 108.15(9) . . ?
C1 N1 C12 125.02(9) . . ?
C1 N2 C2 115.14(10) . . ?
C1 N3 C4 114.94(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
