#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515928.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_1515928
loop_
_publ_author_name
'Greenberg, Sharonna'
'Stephan, Douglas W.'
_publ_section_title
;
 Hydroamination as a route to nitrogen-containing oligomers
;
_journal_issue                   8
_journal_name_full               'Polymer Chemistry'
_journal_page_first              1332
_journal_paper_doi               10.1039/c0py00120a
_journal_volume                  1
_journal_year                    2010
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35
_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                 92.784(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5976(5)
_cell_length_b                   8.3168(6)
_cell_length_c                   31.769(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     1477.2(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9575
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1889
_reflns_number_total             2584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0py00120a.txt
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1515928
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.0749(2) 0.71182(15) 0.15170(4) 0.0256(3) Uani 1 1 d .
C1 C -0.0789(3) 0.65296(18) 0.12479(5) 0.0235(4) Uani 1 1 d .
C2 C -0.2989(3) 0.55920(19) 0.13630(5) 0.0255(4) Uani 1 1 d .
H2B H -0.444(3) 0.6166(19) 0.1227(5) 0.029(4) Uiso 1 1 d .
H2A H -0.314(3) 0.5633(18) 0.1667(5) 0.027(4) Uiso 1 1 d .
C3 C 0.0423(3) 0.69952(18) 0.19574(5) 0.0246(4) Uani 1 1 d .
C4 C -0.1361(3) 0.78613(19) 0.21464(5) 0.0303(4) Uani 1 1 d .
H4A H -0.2408 0.8497 0.1982 0.036 Uiso 1 1 calc R
C5 C -0.1580(3) 0.7780(2) 0.25771(5) 0.0333(4) Uani 1 1 d .
H5A H -0.2787 0.8353 0.2701 0.040 Uiso 1 1 calc R
C6 C -0.0015(3) 0.6851(2) 0.28254(5) 0.0343(4) Uani 1 1 d .
H6A H -0.0168 0.6794 0.3115 0.041 Uiso 1 1 calc R
C7 C 0.1776(3) 0.6010(2) 0.26376(5) 0.0369(4) Uani 1 1 d .
H7A H 0.2831 0.5383 0.2802 0.044 Uiso 1 1 calc R
C8 C 0.2015(3) 0.6092(2) 0.22071(5) 0.0314(4) Uani 1 1 d .
H8A H 0.3248 0.5539 0.2085 0.038 Uiso 1 1 calc R
C9 C -0.0384(3) 0.68154(18) 0.07907(5) 0.0240(4) Uani 1 1 d .
C10 C -0.2056(3) 0.63511(19) 0.04776(5) 0.0295(4) Uani 1 1 d .
H10A H -0.3416 0.5794 0.0550 0.035 Uiso 1 1 calc R
C11 C -0.1729(3) 0.6706(2) 0.00580(5) 0.0372(5) Uani 1 1 d .
H11A H -0.2875 0.6394 -0.0148 0.045 Uiso 1 1 calc R
C12 C 0.0284(4) 0.7518(2) -0.00557(5) 0.0380(5) Uani 1 1 d .
H12A H 0.0511 0.7746 -0.0338 0.046 Uiso 1 1 calc R
C13 C 0.1969(3) 0.7992(2) 0.02543(5) 0.0366(5) Uani 1 1 d .
H13A H 0.3327 0.8548 0.0180 0.044 Uiso 1 1 calc R
C14 C 0.1639(3) 0.76404(19) 0.06714(5) 0.0300(4) Uani 1 1 d .
H14A H 0.2785 0.7959 0.0876 0.036 Uiso 1 1 calc R
C15 C -0.2976(3) 0.38432(18) 0.12302(4) 0.0216(4) Uani 1 1 d .
C16 C -0.1049(3) 0.28490(18) 0.13440(5) 0.0252(4) Uani 1 1 d .
H16A H 0.0281 0.3275 0.1491 0.030 Uiso 1 1 calc R
C17 C -0.1097(3) 0.12320(19) 0.12402(5) 0.0299(4) Uani 1 1 d .
H17A H 0.0194 0.0577 0.1319 0.036 Uiso 1 1 calc R
C18 C -0.3068(3) 0.0587(2) 0.10186(5) 0.0315(4) Uani 1 1 d .
H18A H -0.3097 -0.0497 0.0947 0.038 Uiso 1 1 calc R
C19 C -0.4983(3) 0.15621(19) 0.09052(5) 0.0291(4) Uani 1 1 d .
H19A H -0.6306 0.1135 0.0756 0.035 Uiso 1 1 calc R
C20 C -0.4945(3) 0.31801(18) 0.10127(5) 0.0251(4) Uani 1 1 d .
H20A H -0.6254 0.3826 0.0938 0.030 Uiso 1 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C3 120.97(13)
N1 C1 C9 117.22(14)
N1 C1 C2 124.25(14)
C9 C1 C2 118.53(14)
C15 C2 C1 114.32(13)
C8 C3 C4 119.28(14)
C8 C3 N1 119.48(14)
C4 C3 N1 121.07(14)
C5 C4 C3 120.17(16)
C4 C5 C6 120.46(15)
C7 C6 C5 119.26(15)
C8 C7 C6 120.62(16)
C7 C8 C3 120.18(15)
C10 C9 C14 118.13(14)
C10 C9 C1 121.45(14)
C14 C9 C1 120.33(14)
C9 C10 C11 120.94(16)
C12 C11 C10 120.33(17)
C11 C12 C13 119.33(16)
C14 C13 C12 120.27(16)
C13 C14 C9 120.99(16)
C20 C15 C16 118.68(15)
C20 C15 C2 120.43(14)
C16 C15 C2 120.79(15)
C17 C16 C15 120.60(15)
C16 C17 C18 120.13(16)
C19 C18 C17 119.65(16)
C18 C19 C20 120.23(16)
C15 C20 C19 120.71(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.281(2)
N1 C3 1.4233(18)
C1 C9 1.500(2)
C1 C2 1.517(2)
C2 C15 1.514(2)
C3 C8 1.386(2)
C3 C4 1.391(2)
C4 C5 1.382(2)
C5 C6 1.385(2)
C6 C7 1.381(2)
C7 C8 1.382(2)
C9 C10 1.387(2)
C9 C14 1.392(2)
C10 C11 1.386(2)
C11 C12 1.377(3)
C12 C13 1.388(3)
C13 C14 1.378(2)
C15 C20 1.386(2)
C15 C16 1.393(2)
C16 C17 1.385(2)
C17 C18 1.387(2)
C18 C19 1.378(2)
C19 C20 1.388(2)
