#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515943.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_1515943
loop_
_publ_author_name
'Zhang, Haichang'
'Neudörfl, Jörg-Martin'
'Tieke, Bernd'
_publ_section_title
;
 1,6-Naphthodione-based monomers and polymers
;
_journal_issue                   12
_journal_name_full               'Polymer Chemistry'
_journal_page_first              3754
_journal_paper_doi               10.1039/c4py00388h
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C50 H62 Br2 N2 O2'
_chemical_formula_sum            'C50 H62 Br2 N2 O2'
_chemical_formula_weight         882.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.408(4)
_cell_angle_beta                 94.570(6)
_cell_angle_gamma                95.403(6)
_cell_formula_units_Z            1
_cell_length_a                   5.5633(5)
_cell_length_b                   9.9288(11)
_cell_length_c                   19.482(2)
_cell_measurement_reflns_used    4181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.08
_cell_volume                     1060.22(19)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_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  0.0634
_diffrn_reflns_av_sigmaI/netI    0.1316
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4181
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    1.954
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             462
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .07
_exptl_crystal_size_min          .03
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.929
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0725
_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)+(0.0826P)²+0.8300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                2271
_reflns_number_total             3450
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4py00388h2.cif
_cod_data_source_block           hazh-blau
_cod_depositor_comments          'Adding full bibliography for 1515943.cif.'
_cod_original_cell_volume        1060.19(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 1.68078(13) 0.33753(8) -0.28711(4) 0.0351(3) Uani 1 1 d .
O1 O 1.1857(8) 0.4152(5) 0.0340(3) 0.0324(12) Uani 1 1 d .
N1 N 0.8495(10) 0.2675(5) 0.0461(3) 0.0260(14) Uani 1 1 d .
C1 C 1.4908(12) 0.2962(6) -0.2134(4) 0.0269(17) Uani 1 1 d .
C2 C 1.5735(12) 0.3501(7) -0.1466(4) 0.0262(16) Uani 1 1 d .
H2 H 1.7255 0.4038 -0.1370 0.031 Uiso 1 1 calc R
C3 C 1.4300(12) 0.3241(6) -0.0939(4) 0.0266(16) Uani 1 1 d .
H3 H 1.4840 0.3625 -0.0478 0.032 Uiso 1 1 calc R
C4 C 1.2067(12) 0.2427(6) -0.1064(4) 0.0270(16) Uani 1 1 d .
C5 C 1.0496(12) 0.2180(7) -0.0521(4) 0.0249(16) Uani 1 1 d .
C6 C 1.0474(13) 0.3137(7) 0.0119(4) 0.0274(16) Uani 1 1 d .
C7 C 0.7364(12) 0.1455(6) 0.0105(4) 0.0235(16) Uani 1 1 d .
C8 C 0.8675(12) 0.1149(6) -0.0502(4) 0.0274(17) Uani 1 1 d .
C9 C 0.7963(12) -0.0091(7) -0.0943(4) 0.0276(16) Uani 1 1 d .
H9 H 0.8869 -0.0333 -0.1324 0.033 Uiso 1 1 calc R
C10 C 0.6030(11) -0.0921(6) -0.0828(4) 0.0250(16) Uani 1 1 d .
H10 H 0.5566 -0.1729 -0.1138 0.030 Uiso 1 1 calc R
C11 C 0.5356(11) 0.0622(6) 0.0250(4) 0.0240(16) Uani 1 1 d .
C23 C 1.2727(13) 0.2170(7) -0.2290(4) 0.0288(17) Uani 1 1 d .
H23 H 1.2207 0.1803 -0.2755 0.035 Uiso 1 1 calc R
C24 C 1.1311(12) 0.1918(6) -0.1761(4) 0.0273(17) Uani 1 1 d .
H24 H 0.9786 0.1388 -0.1867 0.033 Uiso 1 1 calc R
C25 C 0.7848(13) 0.3494(7) 0.1072(4) 0.0298(17) Uani 1 1 d .
H25A H 0.6065 0.3503 0.1039 0.036 Uiso 1 1 calc R
H25B H 0.8577 0.4443 0.1074 0.036 Uiso 1 1 calc R
C26 C 0.8660(13) 0.2997(7) 0.1753(4) 0.0330(18) Uani 1 1 d .
H26A H 1.0454 0.3094 0.1815 0.040 Uiso 1 1 calc R
H26B H 0.8095 0.2016 0.1732 0.040 Uiso 1 1 calc R
C27 C 0.7708(13) 0.3766(7) 0.2377(4) 0.0322(18) Uani 1 1 d .
H27A H 0.8234 0.4750 0.2390 0.039 Uiso 1 1 calc R
H27B H 0.5913 0.3646 0.2321 0.039 Uiso 1 1 calc R
C28 C 0.8579(13) 0.3294(7) 0.3060(4) 0.0320(17) Uani 1 1 d .
H28A H 1.0372 0.3439 0.3119 0.038 Uiso 1 1 calc R
H28B H 0.8101 0.2303 0.3038 0.038 Uiso 1 1 calc R
C29 C 0.7587(13) 0.4020(7) 0.3694(4) 0.0316(17) Uani 1 1 d .
H29A H 0.5806 0.3996 0.3604 0.038 Uiso 1 1 calc R
H29B H 0.7918 0.3514 0.4095 0.038 Uiso 1 1 calc R
C30 C 0.8655(12) 0.5495(7) 0.3884(4) 0.0299(17) Uani 1 1 d .
H30A H 1.0415 0.5509 0.4015 0.036 Uiso 1 1 calc R
H30B H 0.8463 0.5976 0.3468 0.036 Uiso 1 1 calc R
C31 C 0.7541(13) 0.6280(7) 0.4473(4) 0.0309(17) Uani 1 1 d .
H31A H 0.7944 0.5895 0.4910 0.037 Uiso 1 1 calc R
H31B H 0.5755 0.6173 0.4377 0.037 Uiso 1 1 calc R
C32 C 0.8458(14) 0.7796(7) 0.4563(4) 0.0368(19) Uani 1 1 d .
H32A H 1.0208 0.7897 0.4721 0.044 Uiso 1 1 calc R
H32B H 0.8289 0.8134 0.4104 0.044 Uiso 1 1 calc R
C33 C 0.7179(14) 0.8697(7) 0.5069(4) 0.039(2) Uani 1 1 d .
H33A H 0.7629 0.9659 0.5002 0.047 Uiso 1 1 calc R
H33B H 0.5408 0.8499 0.4948 0.047 Uiso 1 1 calc R
C34 C 0.7700(13) 0.8548(7) 0.5810(4) 0.0358(19) Uani 1 1 d .
H34A H 0.9456 0.8793 0.5941 0.043 Uiso 1 1 calc R
H34B H 0.7319 0.7579 0.5877 0.043 Uiso 1 1 calc R
C47 C 0.6277(14) 0.9427(8) 0.6298(4) 0.0368(19) Uani 1 1 d .
H47A H 0.6614 1.0392 0.6220 0.044 Uiso 1 1 calc R
H47B H 0.4522 0.9159 0.6177 0.044 Uiso 1 1 calc R
C48 C 0.6875(14) 0.9309(8) 0.7058(4) 0.041(2) Uani 1 1 d .
H48A H 0.6480 0.8364 0.7145 0.061 Uiso 1 1 calc R
H48B H 0.5925 0.9906 0.7337 0.061 Uiso 1 1 calc R
H48C H 0.8607 0.9580 0.7184 0.061 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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
C7 N1 C6 109.7(5) . .
C7 N1 C25 130.4(6) . .
C6 N1 C25 119.8(6) . .
C23 C1 C2 122.3(7) . .
C23 C1 Br1 118.9(6) . .
C2 C1 Br1 118.8(5) . .
C1 C2 C3 118.4(6) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C2 C3 C4 122.1(7) . .
C2 C3 H3 119.0 . .
C4 C3 H3 119.0 . .
C3 C4 C24 116.7(6) . .
C3 C4 C5 122.9(6) . .
C24 C4 C5 120.3(6) . .
C8 C5 C4 129.7(6) . .
C8 C5 C6 106.7(6) . .
C4 C5 C6 123.4(6) . .
O1 C6 N1 123.3(6) . .
O1 C6 C5 129.6(7) . .
N1 C6 C5 107.1(6) . .
C11 C7 N1 130.4(6) . .
C11 C7 C8 122.7(6) . .
N1 C7 C8 107.0(5) . .
C5 C8 C9 132.0(7) . .
C5 C8 C7 109.3(6) . .
C9 C8 C7 118.7(6) . .
C10 C9 C8 120.7(7) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C9 C10 C11 121.8(6) . 2_655
C9 C10 H10 119.1 . .
C11 C10 H10 119.1 2_655 .
C7 C11 C10 124.0(6) . 2_655
C7 C11 C11 115.8(7) . 2_655
C10 C11 C11 120.2(7) 2_655 2_655
C1 C23 C24 118.9(7) . .
C1 C23 H23 120.6 . .
C24 C23 H23 120.6 . .
C23 C24 C4 121.6(6) . .
C23 C24 H24 119.2 . .
C4 C24 H24 119.2 . .
N1 C25 C26 114.2(6) . .
N1 C25 H25A 108.7 . .
C26 C25 H25A 108.7 . .
N1 C25 H25B 108.7 . .
C26 C25 H25B 108.7 . .
H25A C25 H25B 107.6 . .
C25 C26 C27 113.1(6) . .
C25 C26 H26A 109.0 . .
C27 C26 H26A 109.0 . .
C25 C26 H26B 109.0 . .
C27 C26 H26B 109.0 . .
H26A C26 H26B 107.8 . .
C28 C27 C26 113.0(6) . .
C28 C27 H27A 109.0 . .
C26 C27 H27A 109.0 . .
C28 C27 H27B 109.0 . .
C26 C27 H27B 109.0 . .
H27A C27 H27B 107.8 . .
C27 C28 C29 114.2(6) . .
C27 C28 H28A 108.7 . .
C29 C28 H28A 108.7 . .
C27 C28 H28B 108.7 . .
C29 C28 H28B 108.7 . .
H28A C28 H28B 107.6 . .
C30 C29 C28 114.1(6) . .
C30 C29 H29A 108.7 . .
C28 C29 H29A 108.7 . .
C30 C29 H29B 108.7 . .
C28 C29 H29B 108.7 . .
H29A C29 H29B 107.6 . .
C31 C30 C29 115.2(6) . .
C31 C30 H30A 108.5 . .
C29 C30 H30A 108.5 . .
C31 C30 H30B 108.5 . .
C29 C30 H30B 108.5 . .
H30A C30 H30B 107.5 . .
C30 C31 C32 111.8(6) . .
C30 C31 H31A 109.3 . .
C32 C31 H31A 109.3 . .
C30 C31 H31B 109.3 . .
C32 C31 H31B 109.3 . .
H31A C31 H31B 107.9 . .
C33 C32 C31 115.4(6) . .
C33 C32 H32A 108.4 . .
C31 C32 H32A 108.4 . .
C33 C32 H32B 108.4 . .
C31 C32 H32B 108.4 . .
H32A C32 H32B 107.5 . .
C34 C33 C32 115.9(6) . .
C34 C33 H33A 108.3 . .
C32 C33 H33A 108.3 . .
C34 C33 H33B 108.3 . .
C32 C33 H33B 108.3 . .
H33A C33 H33B 107.4 . .
C33 C34 C47 114.0(6) . .
C33 C34 H34A 108.7 . .
C47 C34 H34A 108.7 . .
C33 C34 H34B 108.7 . .
C47 C34 H34B 108.7 . .
H34A C34 H34B 107.6 . .
C48 C47 C34 114.0(6) . .
C48 C47 H47A 108.8 . .
C34 C47 H47A 108.8 . .
C48 C47 H47B 108.8 . .
C34 C47 H47B 108.8 . .
H47A C47 H47B 107.7 . .
C47 C48 H48A 109.5 . .
C47 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C47 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.908(7) .
O1 C6 1.224(8) .
N1 C7 1.394(8) .
N1 C6 1.400(9) .
N1 C25 1.454(8) .
C1 C23 1.375(9) .
C1 C2 1.376(10) .
C2 C3 1.381(10) .
C2 H2 0.9500 .
C3 C4 1.405(9) .
C3 H3 0.9500 .
C4 C24 1.410(10) .
C4 C5 1.453(9) .
C5 C8 1.376(9) .
C5 C6 1.481(9) .
C7 C11 1.392(9) .
C7 C8 1.456(9) .
C8 C9 1.425(9) .
C9 C10 1.341(9) .
C9 H9 0.9500 .
C10 C11 1.435(9) 2_655
C10 H10 0.9500 .
C11 C10 1.435(9) 2_655
C11 C11 1.486(13) 2_655
C23 C24 1.378(10) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C25 C26 1.517(10) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.520(10) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 C28 1.517(10) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 C29 1.529(10) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 C30 1.521(9) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.520(10) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 C32 1.530(9) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 C33 1.520(10) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.477(11) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C47 1.535(10) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C47 C48 1.511(11) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
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_4
C23 C1 C2 C3 -0.6(10) .
Br1 C1 C2 C3 177.4(5) .
C1 C2 C3 C4 1.3(10) .
C2 C3 C4 C24 -2.0(9) .
C2 C3 C4 C5 -177.9(6) .
C3 C4 C5 C8 -159.3(7) .
C24 C4 C5 C8 25.0(11) .
C3 C4 C5 C6 26.6(10) .
C24 C4 C5 C6 -149.2(7) .
C7 N1 C6 O1 -176.3(6) .
C25 N1 C6 O1 6.8(10) .
C7 N1 C6 C5 3.5(7) .
C25 N1 C6 C5 -173.4(6) .
C8 C5 C6 O1 175.2(7) .
C4 C5 C6 O1 -9.5(11) .
C8 C5 C6 N1 -4.6(7) .
C4 C5 C6 N1 170.7(6) .
C6 N1 C7 C11 179.6(7) .
C25 N1 C7 C11 -3.9(11) .
C6 N1 C7 C8 -1.2(7) .
C25 N1 C7 C8 175.3(6) .
C4 C5 C8 C9 10.5(13) .
C6 C5 C8 C9 -174.6(7) .
C4 C5 C8 C7 -171.0(6) .
C6 C5 C8 C7 3.9(8) .
C11 C7 C8 C5 177.5(6) .
N1 C7 C8 C5 -1.8(7) .
C11 C7 C8 C9 -3.8(10) .
N1 C7 C8 C9 176.9(6) .
C5 C8 C9 C10 -177.4(7) .
C7 C8 C9 C10 4.2(10) .
C8 C9 C10 C11 -1.8(10) 2_655
N1 C7 C11 C10 1.6(11) 2_655
C8 C7 C11 C10 -177.5(6) 2_655
N1 C7 C11 C11 -179.9(7) 2_655
C8 C7 C11 C11 1.0(11) 2_655
C2 C1 C23 C24 0.6(10) .
Br1 C1 C23 C24 -177.4(5) .
C1 C23 C24 C4 -1.4(10) .
C3 C4 C24 C23 2.0(9) .
C5 C4 C24 C23 178.0(6) .
C7 N1 C25 C26 81.8(9) .
C6 N1 C25 C26 -102.0(7) .
N1 C25 C26 C27 -173.2(6) .
C25 C26 C27 C28 -178.4(6) .
C26 C27 C28 C29 -178.2(6) .
C27 C28 C29 C30 -71.6(8) .
C28 C29 C30 C31 174.8(6) .
C29 C30 C31 C32 -171.9(6) .
C30 C31 C32 C33 171.6(7) .
C31 C32 C33 C34 71.5(9) .
C32 C33 C34 C47 -177.3(6) .
C33 C34 C47 C48 -178.1(6) .
