#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/79/2017937.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017937
loop_
_publ_author_name
'Mague, Joel T.'
'Chudomel, J. Matthew'
'Lahti, Paul M.'
_publ_section_title
;
 2-Bromo-1,3-bis[2-(2-naphthyl)vinyl]benzene benzene hemisolvate and
 9-bromodinaphth[1,2-a:2',1'-j]anthracene
;
_journal_coeditor_code           GZ3187
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o43
_journal_page_last               o46
_journal_paper_doi               10.1107/S0108270110052297
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C30 H17 Br'
_chemical_formula_moiety         'C30 H17 Br'
_chemical_formula_sum            'C30 H17 Br'
_chemical_formula_weight         457.35
_chemical_name_systematic
;
9-bromodinaphth[1,2-a:2',1'-j]anthracene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.021(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.749(3)
_cell_length_b                   13.2672(17)
_cell_length_c                   7.3108(9)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.66
_cell_measurement_theta_min      2.57
_cell_volume                     1915.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16471
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  0.9185
_exptl_absorpt_correction_T_min  0.7635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0306P)²+1.5496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                3829
_reflns_number_total             4390
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3187.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017937
_cod_database_fobs_code          2017937
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.503111(9) 0.645530(15) 0.35216(3) 0.02390(7) Uani d . 1 . .
C C1 0.59584(9) 0.64305(15) 0.2749(3) 0.0177(4) Uani d . 1 . .
C C2 0.63023(9) 0.73485(14) 0.2628(2) 0.0168(4) Uani d . 1 . .
C C3 0.59744(10) 0.83047(15) 0.2869(3) 0.0202(4) Uani d . 1 . .
H H3 0.5538 0.8335 0.3412 0.024 Uiso calc R 1 . .
C C4 0.62817(10) 0.91569(15) 0.2331(3) 0.0214(4) Uani d . 1 . .
H H4 0.6033 0.9770 0.2331 0.026 Uiso calc R 1 . .
C C5 0.69743(10) 0.91674(14) 0.1756(2) 0.0183(4) Uani d . 1 . .
C C6 0.72771(11) 1.00913(14) 0.1185(3) 0.0217(4) Uani d . 1 . .
H H6 0.7005 1.0679 0.1074 0.026 Uiso calc R 1 . .
C C7 0.79453(11) 1.01424(15) 0.0798(3) 0.0228(4) Uani d . 1 . .
H H7 0.8130 1.0747 0.0313 0.027 Uiso calc R 1 . .
C C8 0.83752(10) 0.92988(15) 0.1110(2) 0.0197(4) Uani d . 1 . .
C C9 0.90859(11) 0.93813(16) 0.0922(3) 0.0243(4) Uani d . 1 . .
H H9 0.9275 0.9987 0.0451 0.029 Uiso calc R 1 . .
C C10 0.95069(11) 0.86065(16) 0.1406(3) 0.0253(4) Uani d . 1 . .
H H10 0.9982 0.8664 0.1224 0.030 Uiso calc R 1 . .
C C11 0.92330(10) 0.77259(16) 0.2173(3) 0.0212(4) Uani d . 1 . .
H H11 0.9525 0.7207 0.2594 0.025 Uiso calc R 1 . .
C C12 0.85418(9) 0.76130(15) 0.2316(2) 0.0179(4) Uani d . 1 . .
H H12 0.8365 0.7012 0.2838 0.021 Uiso calc R 1 . .
C C13 0.80880(9) 0.83661(14) 0.1709(2) 0.0164(4) Uani d . 1 . .
C C14 0.73574(10) 0.82768(14) 0.1830(2) 0.0159(4) Uani d . 1 . .
C C15 0.69954(9) 0.73222(14) 0.2031(2) 0.0152(3) Uani d . 1 . .
C C16 0.72728(9) 0.63963(14) 0.1484(2) 0.0150(3) Uani d . 1 . .
H H16 0.7724 0.6389 0.1032 0.018 Uiso calc R 1 . .
C C17 0.69192(9) 0.54836(14) 0.1569(2) 0.0154(3) Uani d . 1 . .
C C18 0.62258(9) 0.55056(14) 0.2189(2) 0.0170(4) Uani d . 1 . .
C C19 0.58142(10) 0.46240(15) 0.2015(3) 0.0220(4) Uani d . 1 . .
H H19 0.5376 0.4608 0.2552 0.026 Uiso calc R 1 . .
C C20 0.60464(10) 0.38160(15) 0.1091(3) 0.0239(4) Uani d . 1 . .
H H20 0.5746 0.3274 0.0844 0.029 Uiso calc R 1 . .
C C21 0.67309(10) 0.37509(14) 0.0470(3) 0.0198(4) Uani d . 1 . .
C C22 0.69352(11) 0.28761(15) -0.0522(3) 0.0232(4) Uani d . 1 . .
H H22 0.6608 0.2378 -0.0824 0.028 Uiso calc R 1 . .
C C23 0.75859(11) 0.27448(15) -0.1038(3) 0.0226(4) Uani d . 1 . .
H H23 0.7706 0.2190 -0.1792 0.027 Uiso calc R 1 . .
C C24 0.80905(10) 0.34358(14) -0.0453(3) 0.0202(4) Uani d . 1 . .
C C25 0.87833(11) 0.32227(16) -0.0788(3) 0.0246(4) Uani d . 1 . .
H H25 0.8902 0.2657 -0.1519 0.029 Uiso calc R 1 . .
C C26 0.92825(11) 0.38174(17) -0.0077(3) 0.0267(5) Uani d . 1 . .
H H26 0.9744 0.3670 -0.0323 0.032 Uiso calc R 1 . .
C C27 0.91101(10) 0.46476(16) 0.1019(3) 0.0236(4) Uani d . 1 . .
H H27 0.9457 0.5046 0.1556 0.028 Uiso calc R 1 . .
C C28 0.84415(10) 0.48879(14) 0.1320(3) 0.0188(4) Uani d . 1 . .
H H28 0.8337 0.5454 0.2064 0.023 Uiso calc R 1 . .
C C29 0.79055(9) 0.43186(14) 0.0558(2) 0.0170(4) Uani d . 1 . .
C C30 0.71928(9) 0.45265(14) 0.0873(2) 0.0165(4) Uani d . 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C18 . . 124.29(17) ?
C2 C1 Br1 . . 117.91(14) ?
C18 C1 Br1 . . 117.55(14) ?
C1 C2 C3 . . 122.92(17) ?
C1 C2 C15 . . 117.45(17) ?
C3 C2 C15 . . 119.25(17) ?
C4 C3 C2 . . 120.29(18) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 121.78(18) ?
C3 C4 H4 . . 119.1 ?
C5 C4 H4 . . 119.1 ?
C14 C5 C6 . . 120.56(18) ?
C14 C5 C4 . . 119.72(17) ?
C6 C5 C4 . . 119.68(17) ?
C7 C6 C5 . . 120.92(18) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 120.65(18) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C9 C8 C7 . . 121.04(18) ?
C9 C8 C13 . . 119.36(18) ?
C7 C8 C13 . . 119.53(18) ?
C10 C9 C8 . . 121.31(19) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 C11 . . 119.60(19) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.19(19) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 121.83(18) ?
C11 C12 H12 . . 119.1 ?
C13 C12 H12 . . 119.1 ?
C12 C13 C8 . . 117.16(17) ?
C12 C13 C14 . . 123.62(17) ?
C8 C13 C14 . . 118.94(17) ?
C5 C14 C13 . . 117.71(17) ?
C5 C14 C15 . . 117.99(17) ?
C13 C14 C15 . . 124.29(16) ?
C16 C15 C2 . . 118.67(17) ?
C16 C15 C14 . . 122.58(16) ?
C2 C15 C14 . . 118.39(16) ?
C17 C16 C15 . . 123.36(17) ?
C17 C16 H16 . . 118.3 ?
C15 C16 H16 . . 118.3 ?
C16 C17 C18 . . 118.05(16) ?
C16 C17 C30 . . 123.25(16) ?
C18 C17 C30 . . 118.35(16) ?
C1 C18 C19 . . 121.97(17) ?
C1 C18 C17 . . 117.93(17) ?
C19 C18 C17 . . 119.69(17) ?
C20 C19 C18 . . 120.11(18) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C21 . . 121.96(19) ?
C19 C20 H20 . . 119.0 ?
C21 C20 H20 . . 119.0 ?
C30 C21 C22 . . 121.21(18) ?
C30 C21 C20 . . 120.21(18) ?
C22 C21 C20 . . 118.57(18) ?
C23 C22 C21 . . 121.07(19) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C22 C23 C24 . . 120.03(18) ?
C22 C23 H23 . . 120.0 ?
C24 C23 H23 . . 120.0 ?
C25 C24 C23 . . 119.76(18) ?
C25 C24 C29 . . 119.88(18) ?
C23 C24 C29 . . 120.27(18) ?
C26 C25 C24 . . 121.03(19) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C27 . . 119.70(19) ?
C25 C26 H26 . . 120.2 ?
C27 C26 H26 . . 120.2 ?
C28 C27 C26 . . 120.4(2) ?
C28 C27 H27 . . 119.8 ?
C26 C27 H27 . . 119.8 ?
C27 C28 C29 . . 122.08(18) ?
C27 C28 H28 . . 119.0 ?
C29 C28 H28 . . 119.0 ?
C28 C29 C24 . . 116.68(17) ?
C28 C29 C30 . . 124.13(17) ?
C24 C29 C30 . . 118.96(17) ?
C21 C30 C29 . . 117.15(17) ?
C21 C30 C17 . . 117.76(17) ?
C29 C30 C17 . . 125.08(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.9170(18) ?
C1 C2 . 1.397(3) ?
C1 C18 . 1.397(3) ?
C2 C3 . 1.435(3) ?
C2 C15 . 1.437(2) ?
C3 C4 . 1.342(3) y
C3 H3 . 0.9500 ?
C4 C5 . 1.431(3) y
C4 H4 . 0.9500 ?
C5 C14 . 1.404(3) y
C5 C6 . 1.427(3) y
C6 C7 . 1.351(3) y
C6 H6 . 0.9500 ?
C7 C8 . 1.423(3) y
C7 H7 . 0.9500 ?
C8 C9 . 1.415(3) y
C8 C13 . 1.430(3) y
C9 C10 . 1.368(3) y
C9 H9 . 0.9500 ?
C10 C11 . 1.404(3) y
C10 H10 . 0.9500 ?
C11 C12 . 1.377(3) y
C11 H11 . 0.9500 ?
C12 C13 . 1.414(3) y
C12 H12 . 0.9500 ?
C13 C14 . 1.450(3) y
C14 C15 . 1.462(3) y
C15 C16 . 1.403(3) y
C16 C17 . 1.399(3) y
C16 H16 . 0.9500 ?
C17 C18 . 1.443(2) ?
C17 C30 . 1.471(3) y
C18 C19 . 1.430(3) ?
C19 C20 . 1.348(3) y
C19 H19 . 0.9500 ?
C20 C21 . 1.429(3) y
C20 H20 . 0.9500 ?
C21 C30 . 1.406(3) y
C21 C22 . 1.427(3) y
C22 C23 . 1.351(3) y
C22 H22 . 0.9500 ?
C23 C24 . 1.420(3) y
C23 H23 . 0.9500 ?
C24 C25 . 1.419(3) y
C24 C29 . 1.433(3) y
C25 C26 . 1.365(3) y
C25 H25 . 0.9500 ?
C26 C27 . 1.404(3) y
C26 H26 . 0.9500 ?
C27 C28 . 1.376(3) y
C27 H27 . 0.9500 ?
C28 C29 . 1.415(3) y
C28 H28 . 0.9500 ?
C29 C30 . 1.453(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654280
