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

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

data_20150713_pl
_database_code_depnum_ccdc_archive 'CCDC 1415102'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,5-Dimethyl-1-[4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)phenyl]-1H-pyrrole  
;
_chemical_name_common            
1-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-(2-methyl-5-phenyl-1H-pyrrol-1-yl)benzene
_chemical_melting_point          161-162
_chemical_formula_moiety         C23H22N2
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.43

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           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.9535(1)
_cell_length_b                   8.5937(1)
_cell_length_c                   30.8423(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1843.02(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.09

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4927
_diffrn_reflns_av_R_equivalents  0.0088
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4581
_reflns_number_gt                3846
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0615P)²+0.1998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         4581
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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
N1 N 0.59344(16) 0.40109(15) 0.06041(4) 0.0431(3) Uani 1 1 d . . .
N2 N 1.13851(17) 0.48354(15) 0.19331(4) 0.0439(3) Uani 1 1 d . . .
C1 C 0.4715(2) 0.27332(19) 0.05552(4) 0.0430(3) Uani 1 1 d . . .
C2 C 0.3521(2) 0.3076(2) 0.02130(5) 0.0495(4) Uani 1 1 d . . .
H2A H 0.2554 0.2435 0.0106 0.059 Uiso 1 1 calc R . .
C3 C 0.4000(2) 0.4548(2) 0.00532(5) 0.0534(4) Uani 1 1 d . . .
H3A H 0.3405 0.5052 -0.0177 0.064 Uiso 1 1 calc R . .
C4 C 0.5494(2) 0.51202(19) 0.02943(5) 0.0489(4) Uani 1 1 d . . .
C5 C 0.4772(2) 0.1296(2) 0.08103(5) 0.0497(4) Uani 1 1 d . . .
C6 C 0.6377(3) 0.0761(2) 0.10381(6) 0.0637(5) Uani 1 1 d . . .
H6A H 0.7515 0.1329 0.1033 0.076 Uiso 1 1 calc R . .
C7 C 0.6275(4) -0.0625(3) 0.12728(7) 0.0847(7) Uani 1 1 d . . .
H7A H 0.7339 -0.0956 0.1430 0.102 Uiso 1 1 calc R . .
C8 C 0.4628(5) -0.1508(3) 0.12749(8) 0.0912(8) Uani 1 1 d . . .
H8A H 0.4571 -0.2427 0.1433 0.109 Uiso 1 1 calc R . .
C9 C 0.3076(4) -0.1017(3) 0.10409(7) 0.0860(7) Uani 1 1 d . . .
H9A H 0.1970 -0.1625 0.1034 0.103 Uiso 1 1 calc R . .
C10 C 0.3124(3) 0.0366(2) 0.08152(6) 0.0663(5) Uani 1 1 d . . .
H10A H 0.2038 0.0687 0.0663 0.080 Uiso 1 1 calc R . .
C11 C 0.6550(3) 0.6621(2) 0.02547(7) 0.0689(5) Uani 1 1 d . . .
H11A H 0.7531 0.6673 0.0473 0.103 Uiso 1 1 calc R . .
H11B H 0.5669 0.7470 0.0292 0.103 Uiso 1 1 calc R . .
H11C H 0.7132 0.6687 -0.0027 0.103 Uiso 1 1 calc R . .
C12 C 0.73241(19) 0.42548(19) 0.09414(4) 0.0419(3) Uani 1 1 d . . .
C13 C 0.9264(2) 0.4282(2) 0.08417(5) 0.0545(4) Uani 1 1 d . . .
H13A H 0.9666 0.4152 0.0556 0.065 Uiso 1 1 calc R . .
C14 C 1.0601(2) 0.4503(2) 0.11664(5) 0.0545(4) Uani 1 1 d . . .
H14A H 1.1905 0.4540 0.1099 0.065 Uiso 1 1 calc R . .
C15 C 1.00024(19) 0.46697(18) 0.15935(4) 0.0420(3) Uani 1 1 d . . .
C16 C 0.8063(2) 0.4650(2) 0.16910(4) 0.0448(3) Uani 1 1 d . . .
H16A H 0.7661 0.4770 0.1977 0.054 Uiso 1 1 calc R . .
C17 C 0.67159(19) 0.44520(19) 0.13649(4) 0.0443(3) Uani 1 1 d . . .
H17A H 0.5410 0.4452 0.1430 0.053 Uiso 1 1 calc R . .
C18 C 1.1684(2) 0.61784(18) 0.21737(5) 0.0481(3) Uani 1 1 d . . .
C19 C 1.3005(2) 0.5824(2) 0.24831(5) 0.0562(4) Uani 1 1 d . . .
H19A H 1.3475 0.6504 0.2692 0.067 Uiso 1 1 calc R . .
C20 C 1.3542(2) 0.4255(2) 0.24334(5) 0.0556(4) Uani 1 1 d . . .
H20A H 1.4436 0.3724 0.2602 0.067 Uiso 1 1 calc R . .
C21 C 1.2519(2) 0.36502(19) 0.20948(5) 0.0466(3) Uani 1 1 d . . .
C22 C 1.0692(3) 0.7671(2) 0.20727(6) 0.0673(5) Uani 1 1 d . . .
H22A H 1.1098 0.8456 0.2274 0.101 Uiso 1 1 calc R . .
H22B H 0.9326 0.7529 0.2095 0.101 Uiso 1 1 calc R . .
H22C H 1.1012 0.7991 0.1783 0.101 Uiso 1 1 calc R . .
C23 C 1.2376(3) 0.2024(2) 0.19274(6) 0.0661(5) Uani 1 1 d . . .
H23A H 1.3282 0.1375 0.2077 0.099 Uiso 1 1 calc R . .
H23B H 1.2658 0.2014 0.1623 0.099 Uiso 1 1 calc R . .
H23C H 1.1098 0.1637 0.1974 0.099 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.3840(19) . ?
N1 C1 1.395(2) . ?
N1 C12 1.4353(16) . ?
N2 C21 1.381(2) . ?
N2 C18 1.3878(19) . ?
N2 C15 1.4289(17) . ?
C1 C2 1.375(2) . ?
C1 C5 1.465(2) . ?
C2 C3 1.398(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(2) . ?
C3 H3A 0.9300 . ?
C4 C11 1.489(3) . ?
C5 C6 1.397(2) . ?
C5 C10 1.397(3) . ?
C6 C7 1.396(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.365(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.3834(18) . ?
C12 C13 1.384(2) . ?
C13 C14 1.380(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.3890(19) . ?
C14 H14A 0.9300 . ?
C15 C16 1.3817(19) . ?
C16 C17 1.3851(18) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.359(2) . ?
C18 C22 1.489(2) . ?
C19 C20 1.407(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.366(2) . ?
C20 H20A 0.9300 . ?
C21 C23 1.493(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
C4 N1 C1 109.45(12) . . ?
C4 N1 C12 123.29(13) . . ?
C1 N1 C12 127.03(12) . . ?
C21 N2 C18 109.55(11) . . ?
C21 N2 C15 125.13(12) . . ?
C18 N2 C15 125.13(13) . . ?
C2 C1 N1 106.34(14) . . ?
C2 C1 C5 127.50(14) . . ?
N1 C1 C5 126.11(13) . . ?
C1 C2 C3 108.69(14) . . ?
C1 C2 H2A 125.7 . . ?
C3 C2 H2A 125.7 . . ?
C4 C3 C2 108.32(14) . . ?
C4 C3 H3A 125.8 . . ?
C2 C3 H3A 125.8 . . ?
C3 C4 N1 107.19(15) . . ?
C3 C4 C11 129.85(16) . . ?
N1 C4 C11 122.96(14) . . ?
C6 C5 C10 117.52(17) . . ?
C6 C5 C1 124.66(16) . . ?
C10 C5 C1 117.78(16) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C9 C10 C5 121.2(2) . . ?
C9 C10 H10A 119.4 . . ?
C5 C10 H10A 119.4 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.38(12) . . ?
C17 C12 N1 119.76(12) . . ?
C13 C12 N1 119.85(12) . . ?
C14 C13 C12 119.87(13) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 120.03(13) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C16 C15 C14 119.87(12) . . ?
C16 C15 N2 119.88(12) . . ?
C14 C15 N2 120.24(12) . . ?
C15 C16 C17 120.23(12) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C12 C17 C16 119.60(12) . . ?
C12 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C19 C18 N2 106.87(14) . . ?
C19 C18 C22 130.76(15) . . ?
N2 C18 C22 122.36(14) . . ?
C18 C19 C20 108.51(14) . . ?
C18 C19 H19A 125.7 . . ?
C20 C19 H19A 125.7 . . ?
C21 C20 C19 108.05(15) . . ?
C21 C20 H20A 126.0 . . ?
C19 C20 H20A 126.0 . . ?
C20 C21 N2 107.01(14) . . ?
C20 C21 C23 130.93(16) . . ?
N2 C21 C23 121.82(14) . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 N1 C1 C2 -0.20(16) . . . . ?
C12 N1 C1 C2 174.37(13) . . . . ?
C4 N1 C1 C5 177.60(13) . . . . ?
C12 N1 C1 C5 -7.8(2) . . . . ?
N1 C1 C2 C3 0.00(16) . . . . ?
C5 C1 C2 C3 -177.75(14) . . . . ?
C1 C2 C3 C4 0.19(17) . . . . ?
C2 C3 C4 N1 -0.31(17) . . . . ?
C2 C3 C4 C11 179.18(17) . . . . ?
C1 N1 C4 C3 0.32(16) . . . . ?
C12 N1 C4 C3 -174.49(13) . . . . ?
C1 N1 C4 C11 -179.22(15) . . . . ?
C12 N1 C4 C11 6.0(2) . . . . ?
C2 C1 C5 C6 155.37(16) . . . . ?
N1 C1 C5 C6 -22.0(2) . . . . ?
C2 C1 C5 C10 -22.5(2) . . . . ?
N1 C1 C5 C10 160.19(15) . . . . ?
C10 C5 C6 C7 -2.4(2) . . . . ?
C1 C5 C6 C7 179.77(16) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -2.0(4) . . . . ?
C8 C9 C10 C5 1.4(3) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C1 C5 C10 C9 178.79(16) . . . . ?
C4 N1 C12 C17 108.26(17) . . . . ?
C1 N1 C12 C17 -65.6(2) . . . . ?
C4 N1 C12 C13 -72.1(2) . . . . ?
C1 N1 C12 C13 114.03(18) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
N1 C12 C13 C14 -179.42(16) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C13 C14 C15 N2 177.47(16) . . . . ?
C21 N2 C15 C16 104.93(18) . . . . ?
C18 N2 C15 C16 -69.6(2) . . . . ?
C21 N2 C15 C14 -74.0(2) . . . . ?
C18 N2 C15 C14 111.45(18) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
N2 C15 C16 C17 -178.44(14) . . . . ?
C13 C12 C17 C16 -1.2(3) . . . . ?
N1 C12 C17 C16 178.46(15) . . . . ?
C15 C16 C17 C12 0.8(2) . . . . ?
C21 N2 C18 C19 0.15(18) . . . . ?
C15 N2 C18 C19 175.42(14) . . . . ?
C21 N2 C18 C22 178.77(15) . . . . ?
C15 N2 C18 C22 -6.0(2) . . . . ?
N2 C18 C19 C20 0.38(19) . . . . ?
C22 C18 C19 C20 -178.07(18) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C19 C20 C21 N2 0.86(19) . . . . ?
C19 C20 C21 C23 -173.48(18) . . . . ?
C18 N2 C21 C20 -0.64(18) . . . . ?
C15 N2 C21 C20 -175.90(13) . . . . ?
C18 N2 C21 C23 174.34(15) . . . . ?
C15 N2 C21 C23 -0.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.030
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/hexane with a trace amount of dichroromethane '
