#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180216 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/02/7110287.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_7110287
loop_
_publ_author_name
'Choytun, Dharinee D.'
'Langlois, Lisa D.'
'Johansson, Thomas P.'
'Macdonald, Charles L. B.'
'Leach, Gary W.'
'Weinberg, Noham'
'Clyburne, Jason A. C.'
_publ_section_title
;
 Azines possessing strong push?pull donors/acceptorsElectronic
 supplementary information (ESI) available: characterisation data, CIF
 files, atomic coordinates, bond length correlations, and details of the
 SHG studies. See http://www.rsc.org/suppdata/cc/b4/b404129a/
;
_journal_issue                   16
_journal_name_full               'Chemical Communications'
_journal_page_first              1842
_journal_page_last               1843
_journal_paper_doi               10.1039/b404129a
_journal_year                    2004
_chemical_formula_sum            'C34 H30 Br2 N4'
_chemical_formula_weight         654.44
_chemical_name_systematic
;
?
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.242(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1477(7)
_cell_length_b                   20.9731(13)
_cell_length_c                   14.0060(8)
_cell_measurement_temperature    173(2)
_cell_volume                     3008.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1293
_diffrn_reflns_av_sigmaI/netI    0.1361
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28975
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.164
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1996
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2282
_reflns_number_gt                2909
_reflns_number_total             6935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b404129asup1.cif
_cod_data_source_block           p1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7110287
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_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
C01 C 0.3267(7) 0.0851(3) 0.1859(6) 0.0390(17) Uani 1 1 d .
C03 C 0.2031(7) 0.0421(4) 0.2611(6) 0.046(2) Uani 1 1 d .
H03 H 0.1750 0.0284 0.3120 0.056 Uiso 1 1 calc R
C04 C 0.1354(8) 0.0385(4) 0.1585(6) 0.051(2) Uani 1 1 d .
H04 H 0.0523 0.0213 0.1250 0.062 Uiso 1 1 calc R
C11 C 0.5106(7) 0.1566(3) 0.0722(5) 0.0349(16) Uani 1 1 d .
C12 C 0.6507(7) 0.1674(3) 0.1436(5) 0.0359(17) Uani 1 1 d .
C13 C 0.7166(7) 0.1550(3) 0.2467(6) 0.0397(17) Uani 1 1 d .
H13 H 0.6751 0.1361 0.2855 0.048 Uiso 1 1 calc R
C14 C 0.8482(8) 0.1716(4) 0.2921(5) 0.045(2) Uani 1 1 d .
C15 C 0.9133(7) 0.2007(3) 0.2365(6) 0.0413(18) Uani 1 1 d .
H15 H 1.0014 0.2111 0.2688 0.050 Uiso 1 1 calc R
C16 C 0.8436(7) 0.2139(3) 0.1321(6) 0.0438(19) Uani 1 1 d .
H16 H 0.8851 0.2334 0.0939 0.053 Uiso 1 1 calc R
C17 C 0.7114(7) 0.1979(3) 0.0839(6) 0.0379(17) Uani 1 1 d .
C18 C 0.6170(7) 0.2057(3) -0.0217(6) 0.0392(17) Uani 1 1 d .
C19 C 0.6248(8) 0.2329(4) -0.1087(6) 0.0452(19) Uani 1 1 d .
H19 H 0.7030 0.2503 -0.1055 0.054 Uiso 1 1 calc R
C21 C 0.4221(7) 0.0874(4) 0.3787(6) 0.045(2) Uani 1 1 d .
C22 C 0.5407(9) 0.0546(4) 0.4129(7) 0.058(2) Uani 1 1 d .
C23 C 0.6344(8) 0.0737(5) 0.5107(7) 0.064(3) Uani 1 1 d .
H23 H 0.7161 0.0543 0.5354 0.076 Uiso 1 1 calc R
C24 C 0.6104(9) 0.1195(4) 0.5706(7) 0.060(2) Uani 1 1 d .
C25 C 0.4909(8) 0.1492(4) 0.5319(7) 0.056(2) Uani 1 1 d .
H25 H 0.4731 0.1805 0.5714 0.068 Uiso 1 1 calc R
C26 C 0.3961(7) 0.1335(4) 0.4355(6) 0.0447(19) Uani 1 1 d .
C31 C 0.1796(7) 0.0590(3) 0.0007(6) 0.0429(18) Uani 1 1 d .
C32 C 0.2360(8) 0.0093(4) -0.0332(6) 0.052(2) Uani 1 1 d .
C33 C 0.2050(8) 0.0033(4) -0.1378(6) 0.056(2) Uani 1 1 d .
H33 H 0.2438 -0.0291 -0.1609 0.067 Uiso 1 1 calc R
C34 C 0.1172(8) 0.0442(4) -0.2106(6) 0.048(2) Uani 1 1 d .
C35 C 0.0643(7) 0.0931(4) -0.1733(6) 0.047(2) Uani 1 1 d .
H35 H 0.0076 0.1217 -0.2205 0.057 Uiso 1 1 calc R
C36 C 0.0926(7) 0.1012(4) -0.0677(6) 0.0420(18) Uani 1 1 d .
C110 C 0.5138(8) 0.2341(4) -0.2018(6) 0.054(2) Uani 1 1 d .
H110 H 0.5179 0.2527 -0.2608 0.064 Uiso 1 1 calc R
C111 C 0.3992(8) 0.2079(4) -0.2062(6) 0.050(2) Uani 1 1 d .
C112 C 0.3863(8) 0.1804(4) -0.1237(6) 0.049(2) Uani 1 1 d .
H112 H 0.3076 0.1622 -0.1298 0.058 Uiso 1 1 calc R
C113 C 0.4946(7) 0.1800(3) -0.0288(6) 0.0372(17) Uani 1 1 d .
C221 C 0.5685(9) 0.0023(5) 0.3514(8) 0.077(3) Uani 1 1 d .
H22A H 0.4938 -0.0040 0.2876 0.115 Uiso 1 1 calc R
H22B H 0.5871 -0.0365 0.3910 0.115 Uiso 1 1 calc R
H22C H 0.6424 0.0138 0.3362 0.115 Uiso 1 1 calc R
C241 C 0.7129(10) 0.1359(5) 0.6765(8) 0.096(4) Uani 1 1 d .
H24A H 0.6808 0.1691 0.7072 0.143 Uiso 1 1 calc R
H24B H 0.7908 0.1501 0.6693 0.143 Uiso 1 1 calc R
H24C H 0.7322 0.0988 0.7201 0.143 Uiso 1 1 calc R
C261 C 0.2668(7) 0.1687(4) 0.3941(6) 0.054(2) Uani 1 1 d .
H26A H 0.2656 0.1994 0.4445 0.081 Uiso 1 1 calc R
H26B H 0.1968 0.1388 0.3809 0.081 Uiso 1 1 calc R
H26C H 0.2562 0.1901 0.3307 0.081 Uiso 1 1 calc R
C321 C 0.3356(11) -0.0344(4) 0.0452(7) 0.085(3) Uani 1 1 d .
H32A H 0.3448 -0.0230 0.1141 0.128 Uiso 1 1 calc R
H32B H 0.4183 -0.0299 0.0396 0.128 Uiso 1 1 calc R
H32C H 0.3067 -0.0778 0.0314 0.128 Uiso 1 1 calc R
C341 C 0.0855(9) 0.0365(4) -0.3253(6) 0.066(3) Uani 1 1 d .
H34A H 0.1315 0.0003 -0.3360 0.098 Uiso 1 1 calc R
H34B H 0.1117 0.0742 -0.3511 0.098 Uiso 1 1 calc R
H34C H -0.0067 0.0302 -0.3619 0.098 Uiso 1 1 calc R
C361 C 0.0348(9) 0.1549(4) -0.0311(7) 0.069(3) Uani 1 1 d .
H36A H -0.0226 0.1788 -0.0898 0.104 Uiso 1 1 calc R
H36B H 0.1032 0.1822 0.0133 0.104 Uiso 1 1 calc R
H36C H -0.0136 0.1383 0.0069 0.104 Uiso 1 1 calc R
N1 N 0.4357(6) 0.1135(3) 0.1827(4) 0.0422(15) Uani 1 1 d .
N2 N 0.4088(6) 0.1318(3) 0.0863(4) 0.0402(15) Uani 1 1 d .
N02 N 0.3243(6) 0.0703(3) 0.2783(5) 0.0438(15) Uani 1 1 d .
N05 N 0.2128(6) 0.0655(3) 0.1105(5) 0.0433(15) Uani 1 1 d .
Br1 Br 0.94232(8) 0.15389(4) 0.43552(6) 0.0564(3) Uani 1 1 d .
Br2 Br 0.24978(10) 0.20984(5) -0.33481(7) 0.0747(4) Uani 1 1 d .
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'
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
N02 C01 N05 108.2(6)
N02 C01 N1 119.3(7)
N05 C01 N1 132.5(7)
C04 C03 N02 107.8(6)
C03 C04 N05 107.4(7)
N2 C11 C113 119.8(6)
N2 C11 C12 133.0(6)
C113 C11 C12 107.2(6)
C13 C12 C17 121.9(7)
C13 C12 C11 131.3(6)
C17 C12 C11 106.8(6)
C12 C13 C14 117.8(7)
C13 C14 C15 122.7(7)
C13 C14 Br1 118.5(6)
C15 C14 Br1 118.9(6)
C16 C15 C14 118.5(7)
C15 C16 C17 120.5(7)
C16 C17 C12 118.7(7)
C16 C17 C18 132.1(6)
C12 C17 C18 109.2(6)
C19 C18 C113 119.0(7)
C19 C18 C17 132.5(7)
C113 C18 C17 108.4(6)
C18 C19 C110 119.4(7)
C26 C21 C22 122.9(8)
C26 C21 N02 119.7(7)
C22 C21 N02 117.4(8)
C21 C22 C23 115.5(8)
C21 C22 C221 123.0(9)
C23 C22 C221 121.5(8)
C24 C23 C22 122.9(8)
C25 C24 C23 118.0(9)
C25 C24 C241 121.7(10)
C23 C24 C241 120.3(9)
C24 C25 C26 121.7(9)
C21 C26 C25 119.0(7)
C21 C26 C261 121.0(7)
C25 C26 C261 120.0(7)
C36 C31 C32 122.0(7)
C36 C31 N05 119.6(6)
C32 C31 N05 118.3(7)
C33 C32 C31 118.3(8)
C33 C32 C321 121.4(7)
C31 C32 C321 120.2(7)
C32 C33 C34 122.3(8)
C35 C34 C33 117.4(7)
C35 C34 C341 121.6(8)
C33 C34 C341 121.0(7)
C34 C35 C36 122.6(7)
C31 C36 C35 117.4(7)
C31 C36 C361 121.8(7)
C35 C36 C361 120.8(7)
C111 C110 C19 120.0(7)
C112 C111 C110 123.1(7)
C112 C111 Br2 118.0(6)
C110 C111 Br2 118.9(6)
C111 C112 C113 118.2(7)
C112 C113 C18 120.2(6)
C112 C113 C11 131.4(6)
C18 C113 C11 108.4(6)
N2 N1 C01 108.3(6)
N1 N2 C11 113.8(6)
C01 N02 C03 108.4(6)
C01 N02 C21 125.9(6)
C03 N02 C21 125.3(6)
C01 N05 C04 108.2(6)
C01 N05 C31 129.0(6)
C04 N05 C31 121.6(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C01 N02 1.342(9)
C01 N05 1.356(9)
C01 N1 1.370(9)
C03 C04 1.335(10)
C03 N02 1.405(9)
C04 N05 1.406(9)
C11 N2 1.331(9)
C11 C113 1.440(10)
C11 C12 1.503(10)
C12 C13 1.363(10)
C12 C17 1.419(9)
C13 C14 1.393(10)
C14 C15 1.398(10)
C14 Br1 1.900(7)
C15 C16 1.385(10)
C16 C17 1.398(10)
C17 C18 1.447(10)
C18 C19 1.378(9)
C18 C113 1.434(9)
C19 C110 1.400(11)
C21 C26 1.354(10)
C21 C22 1.397(11)
C21 N02 1.444(9)
C22 C23 1.414(12)
C22 C221 1.501(12)
C23 C24 1.371(13)
C24 C25 1.372(12)
C24 C241 1.511(12)
C25 C26 1.386(10)
C26 C261 1.517(10)
C31 C36 1.383(10)
C31 C32 1.395(10)
C31 N05 1.438(9)
C32 C33 1.371(11)
C32 C321 1.521(11)
C33 C34 1.396(11)
C34 C35 1.384(10)
C34 C341 1.511(10)
C35 C36 1.396(10)
C36 C361 1.485(10)
C110 C111 1.370(11)
C111 C112 1.348(10)
C111 Br2 1.912(8)
C112 C113 1.399(10)
N1 N2 1.319(7)
