#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/31/7203187.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7203187
loop_
_publ_author_name
'José Giner Planas'
'Carles Masalles'
'Reijo Sillanpää'
'Raikko Kivekäs'
'Francesc Teixidor'
'Clara Viñas'
_publ_section_title
;
 Synthesis and solid state structure for a series of
 poly(1-pyrrolylmethyl)benzene derivatives. Control of the interplaying
 π--π and C--Hπ interactions?
;
_journal_name_full               CrystEngComm
_journal_page_first              75
_journal_page_last               83
_journal_paper_doi               10.1039/b515930j
_journal_year                    2006
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_formula_weight         236.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.875(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2058(9)
_cell_length_b                   5.6582(12)
_cell_length_c                   25.114(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      17.1
_cell_measurement_theta_min      10.5
_cell_volume                     1298.7(3)
_computing_cell_refinement       'CAD4 EXPRESS (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 EXPRESS (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms, 1996)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       ω--θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2352
_diffrn_reflns_theta_full        66.86
_diffrn_reflns_theta_max         66.86
_diffrn_reflns_theta_min         3.55
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.9623
_exptl_absorpt_correction_T_min  0.8300
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Sheldrick, G.M. (anon) SHELX97 Release 97-2 (1998)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0886P)²+0.1102P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                1528
_reflns_number_total             2299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b515930j.txt
_cod_data_source_block           compound_4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7203187
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'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N8 N 0.3835(2) 0.0971(4) 0.21629(7) 0.0263(5) Uani 1 d . . .
N14 N 0.1711(2) 0.8967(4) -0.00939(7) 0.0248(5) Uani 1 d . . .
C1 C 0.3164(3) 0.3486(4) 0.13621(8) 0.0239(6) Uani 1 d . . .
C2 C 0.2229(2) 0.5185(5) 0.11155(8) 0.0234(6) Uani 1 d . . .
H2 H 0.1279 0.5354 0.1223 0.028 Uiso 1 calc R . .
C3 C 0.2643(3) 0.6650(4) 0.07153(8) 0.0228(5) Uani 1 d . . .
C4 C 0.4042(3) 0.6367(5) 0.05618(9) 0.0283(6) Uani 1 d . . .
H4 H 0.4350 0.7350 0.0290 0.034 Uiso 1 calc R . .
C5 C 0.4974(3) 0.4682(5) 0.07999(9) 0.0346(7) Uani 1 d . . .
H5 H 0.5919 0.4504 0.0689 0.042 Uiso 1 calc R . .
C6 C 0.4556(3) 0.3237(5) 0.11994(9) 0.0295(6) Uani 1 d . . .
H6 H 0.5212 0.2079 0.1362 0.035 Uiso 1 calc R . .
C7 C 0.2653(3) 0.1921(5) 0.17918(9) 0.0321(6) Uani 1 d . . .
H7A H 0.1994 0.2845 0.1996 0.038 Uiso 1 calc R . .
H7B H 0.2081 0.0592 0.1617 0.038 Uiso 1 calc R . .
C9 C 0.4568(3) 0.2191(5) 0.25786(9) 0.0351(7) Uani 1 d . . .
H9 H 0.4319 0.3717 0.2697 0.042 Uiso 1 calc R . .
C10 C 0.5710(3) 0.0862(6) 0.27946(10) 0.0431(8) Uani 1 d . . .
H10 H 0.6395 0.1282 0.3093 0.052 Uiso 1 calc R . .
C11 C 0.5702(3) -0.1244(6) 0.25004(10) 0.0406(7) Uani 1 d . . .
H11 H 0.6379 -0.2512 0.2560 0.049 Uiso 1 calc R . .
C12 C 0.4539(3) -0.1120(5) 0.21136(9) 0.0331(6) Uani 1 d . . .
H12 H 0.4261 -0.2299 0.1852 0.040 Uiso 1 calc R . .
C13 C 0.1630(3) 0.8561(5) 0.04773(8) 0.0294(6) Uani 1 d . . .
H13A H 0.0613 0.8129 0.0527 0.035 Uiso 1 calc R . .
H13B H 0.1870 1.0052 0.0675 0.035 Uiso 1 calc R . .
C15 C 0.1175(3) 0.7493(5) -0.04982(9) 0.0307(6) Uani 1 d . . .
H15 H 0.0675 0.6046 -0.0459 0.037 Uiso 1 calc R . .
C16 C 0.1480(3) 0.8458(6) -0.09700(9) 0.0386(7) Uani 1 d . . .
H16 H 0.1221 0.7819 -0.1318 0.046 Uiso 1 calc R . .
C17 C 0.2244(3) 1.0554(6) -0.08464(10) 0.0421(8) Uani 1 d . . .
H17 H 0.2610 1.1596 -0.1095 0.051 Uiso 1 calc R . .
C18 C 0.2369(3) 1.0839(5) -0.03040(10) 0.0336(6) Uani 1 d . . .
H18 H 0.2834 1.2121 -0.0108 0.040 Uiso 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C9 N8 C12 108.2(2) . . ?
C9 N8 C7 124.8(2) . . ?
C12 N8 C7 126.3(2) . . ?
C18 N14 C15 109.1(2) . . ?
C18 N14 C13 125.5(2) . . ?
C15 N14 C13 125.4(2) . . ?
C2 C1 C6 118.8(2) . . ?
C2 C1 C7 119.7(2) . . ?
C6 C1 C7 121.5(2) . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 C13 120.3(2) . . ?
C4 C3 C13 121.4(2) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N8 C7 C1 113.7(2) . . ?
N8 C7 H7A 108.8 . . ?
C1 C7 H7A 108.8 . . ?
N8 C7 H7B 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C10 C9 N8 108.4(3) . . ?
C10 C9 H9 125.8 . . ?
N8 C9 H9 125.8 . . ?
C9 C10 C11 107.9(2) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
C12 C11 C10 106.6(3) . . ?
C12 C11 H11 126.7 . . ?
C10 C11 H11 126.7 . . ?
C11 C12 N8 108.8(2) . . ?
C11 C12 H12 125.6 . . ?
N8 C12 H12 125.6 . . ?
N14 C13 C3 113.62(19) . . ?
N14 C13 H13A 108.8 . . ?
C3 C13 H13A 108.8 . . ?
N14 C13 H13B 108.8 . . ?
C3 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N14 C15 C16 108.0(2) . . ?
N14 C15 H15 126.0 . . ?
C16 C15 H15 126.0 . . ?
C15 C16 C17 107.3(2) . . ?
C15 C16 H16 126.3 . . ?
C17 C16 H16 126.3 . . ?
C18 C17 C16 107.7(2) . . ?
C18 C17 H17 126.2 . . ?
C16 C17 H17 126.2 . . ?
N14 C18 C17 107.9(3) . . ?
N14 C18 H18 126.0 . . ?
C17 C18 H18 126.0 . . ?
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
N8 C9 1.361(3) . ?
N8 C12 1.362(3) . ?
N8 C7 1.449(3) . ?
N14 C18 1.358(3) . ?
N14 C15 1.360(3) . ?
N14 C13 1.463(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.514(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 C13 1.504(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.352(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.359(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C16 1.364(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
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
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 C1 C2 C3 -179.4(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C13 -176.7(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C13 C3 C4 C5 177.1(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C7 C1 C6 C5 179.1(2) . . . . ?
C9 N8 C7 C1 78.7(3) . . . . ?
C12 N8 C7 C1 -91.1(3) . . . . ?
C2 C1 C7 N8 -155.5(2) . . . . ?
C6 C1 C7 N8 25.6(3) . . . . ?
C12 N8 C9 C10 -0.9(3) . . . . ?
C7 N8 C9 C10 -172.3(2) . . . . ?
N8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 N8 -0.3(3) . . . . ?
C9 N8 C12 C11 0.8(3) . . . . ?
C7 N8 C12 C11 172.0(2) . . . . ?
C18 N14 C13 C3 -105.4(3) . . . . ?
C15 N14 C13 C3 72.6(3) . . . . ?
C2 C3 C13 N14 -145.3(2) . . . . ?
C4 C3 C13 N14 37.8(3) . . . . ?
C18 N14 C15 C16 -0.8(3) . . . . ?
C13 N14 C15 C16 -179.0(2) . . . . ?
N14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C15 N14 C18 C17 0.2(3) . . . . ?
C13 N14 C18 C17 178.5(2) . . . . ?
C16 C17 C18 N14 0.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149468
