#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:23:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180427 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/96/7209605.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_7209605
loop_
_publ_author_name
'Pang, Xue'
'Wang, Hui'
'Zhao, Xiao Ran'
'Jin, Wei Jun'
_publ_section_title
;
 Co-crystallization turned on the phosphorescence of phenanthrene by
 C--Br⋯π halogen bonding, π--hole⋯π bonding and other
 assisting interactions
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2722
_journal_paper_doi               10.1039/c3ce26661c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C54 H30 Br4 F8'
_chemical_formula_weight         1150.42
_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                83.047(2)
_cell_angle_beta                 84.916(2)
_cell_angle_gamma                79.039(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9513(10)
_cell_length_b                   8.9349(13)
_cell_length_c                   17.922(2)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.71
_cell_volume                     1082.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      110(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5369
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    3.793
_exptl_absorpt_correction_T_max  0.6589
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             566
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0710
_reflns_number_gt                3057
_reflns_number_total             3798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce26661c.txt
_cod_data_source_block           120330a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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      P-1
_cod_database_code               7209605
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.99040(4) 0.21908(4) 0.012102(16) 0.02269(10) Uani 1 1 d . . .
Br2 Br 0.76951(5) 0.24094(4) 0.372573(16) 0.03002(11) Uani 1 1 d . . .
C1 C 0.9380(4) 0.2289(3) 0.11571(15) 0.0172(6) Uani 1 1 d U . .
C2 C 0.9815(4) 0.0987(3) 0.16605(16) 0.0184(7) Uani 1 1 d U . .
C3 C 0.9342(4) 0.1039(3) 0.24188(16) 0.0192(7) Uani 1 1 d U . .
C4 C 0.8424(4) 0.2376(3) 0.26990(16) 0.0183(7) Uani 1 1 d U . .
C5 C 0.8006(4) 0.3690(3) 0.21998(16) 0.0175(6) Uani 1 1 d U . .
C6 C 0.8494(4) 0.3643(3) 0.14396(15) 0.0165(6) Uani 1 1 d U . .
C7 C 0.4329(4) 0.1536(3) 0.19747(16) 0.0174(6) Uani 1 1 d U . .
C8 C 0.4692(4) 0.0218(3) 0.24922(17) 0.0230(7) Uani 1 1 d U . .
H8 H 0.4329 0.0292 0.3012 0.028 Uiso 1 1 calc R . .
C9 C 0.5558(5) -0.1168(4) 0.22592(18) 0.0282(8) Uani 1 1 d U . .
H9 H 0.5766 -0.2047 0.2618 0.034 Uiso 1 1 calc R . .
C10 C 0.6146(4) -0.1315(4) 0.14958(18) 0.0269(7) Uani 1 1 d U . .
H10 H 0.6761 -0.2280 0.1340 0.032 Uiso 1 1 calc R . .
C11 C 0.5820(4) -0.0047(4) 0.09826(17) 0.0220(7) Uani 1 1 d U . .
H11 H 0.6215 -0.0140 0.0466 0.026 Uiso 1 1 calc R . .
C12 C 0.4910(4) 0.1396(3) 0.12040(16) 0.0166(6) Uani 1 1 d U . .
C13 C 0.4547(4) 0.2714(4) 0.06617(17) 0.0222(7) Uani 1 1 d U . .
H13 H 0.4920 0.2609 0.0145 0.027 Uiso 1 1 calc R . .
C14 C 0.3692(4) 0.4098(4) 0.08664(16) 0.0222(7) Uani 1 1 d U . .
H14 H 0.3474 0.4949 0.0492 0.027 Uiso 1 1 calc R . .
C15 C 0.3106(4) 0.4312(3) 0.16329(17) 0.0220(7) Uani 1 1 d U . .
C16 C 0.2202(5) 0.5758(4) 0.18484(19) 0.0302(8) Uani 1 1 d U . .
H16 H 0.2010 0.6613 0.1475 0.036 Uiso 1 1 calc R . .
C17 C 0.1595(5) 0.5964(4) 0.2580(2) 0.0348(9) Uani 1 1 d U . .
H17 H 0.0973 0.6947 0.2712 0.042 Uiso 1 1 calc R . .
C18 C 0.1896(5) 0.4715(4) 0.31312(19) 0.0330(8) Uani 1 1 d U . .
H18 H 0.1481 0.4854 0.3642 0.040 Uiso 1 1 calc R . .
C19 C 0.2782(4) 0.3289(4) 0.29473(17) 0.0229(7) Uani 1 1 d U . .
H19 H 0.2978 0.2455 0.3332 0.027 Uiso 1 1 calc R . .
C20 C 0.3405(4) 0.3046(3) 0.21969(16) 0.0179(6) Uani 1 1 d U . .
C21 C 0.4483(7) 0.9424(4) 0.4769(2) 0.0237(15) Uani 0.50 1 d PGU A -1
C22 C 0.2833(5) 0.9166(5) 0.4455(3) 0.0287(17) Uani 0.50 1 d PGU A -1
H22 H 0.1670 0.9922 0.4450 0.034 Uiso 0.50 1 calc PR A -1
C23 C 0.2884(6) 0.7800(5) 0.4149(3) 0.0323(16) Uani 0.50 1 d PGU A -1
H23 H 0.1757 0.7624 0.3934 0.039 Uiso 0.50 1 calc PR A -1
C24 C 0.4586(7) 0.6694(4) 0.4157(3) 0.0301(16) Uani 0.50 1 d PGU A -1
H24 H 0.4622 0.5761 0.3948 0.036 Uiso 0.50 1 calc PR A -1
C25 C 0.6236(6) 0.6952(4) 0.4471(3) 0.0306(16) Uani 0.50 1 d PGU A -1
H25 H 0.7399 0.6196 0.4476 0.037 Uiso 0.50 1 calc PR A -1
C26 C 0.6184(5) 0.8318(5) 0.4777(2) 0.0257(15) Uani 0.50 1 d PGDU A -1
C27 C 0.7821(8) 0.8572(7) 0.5110(3) 0.0294(16) Uani 0.50 1 d PDU A -1
H27 H 0.8982 0.7814 0.5108 0.035 Uiso 0.50 1 calc PR A -1
C28 C 0.7799(10) 0.9897(7) 0.5442(3) 0.0278(16) Uani 0.50 1 d PDU A -1
H28 H 0.8917 1.0033 0.5677 0.033 Uiso 0.50 1 calc PR A -1
C29 C 0.6046(6) 1.1076(5) 0.5426(3) 0.029(2) Uiso 0.50 1 d PG A -1
C30 C 0.6091(6) 1.2406(6) 0.5749(3) 0.036(2) Uiso 0.50 1 d PG A -1
H30 H 0.7241 1.2517 0.5971 0.044 Uiso 0.50 1 calc PR A -1
C31 C 0.4454(8) 1.3574(5) 0.5748(3) 0.034(2) Uiso 0.50 1 d PG A -1
H31 H 0.4485 1.4482 0.5969 0.041 Uiso 0.50 1 calc PR A -1
C32 C 0.2771(6) 1.3411(5) 0.5424(3) 0.037(2) Uiso 0.50 1 d PG A -1
H32 H 0.1652 1.4209 0.5423 0.044 Uiso 0.50 1 calc PR A -1
C33 C 0.2726(6) 1.2082(6) 0.5101(3) 0.0330(19) Uiso 0.50 1 d PG A -1
H33 H 0.1576 1.1971 0.4879 0.040 Uiso 0.50 1 calc PR A -1
C34 C 0.4363(8) 1.0914(5) 0.5102(3) 0.0222(17) Uiso 0.50 1 d PG A -1
F1 F 1.0699(2) -0.03519(19) 0.14096(9) 0.0256(4) Uani 1 1 d . . .
F2 F 0.9787(3) -0.02522(19) 0.28889(10) 0.0300(4) Uani 1 1 d . . .
F3 F 0.7126(2) 0.50150(19) 0.24460(9) 0.0247(4) Uani 1 1 d . . .
F4 F 0.8081(2) 0.49315(18) 0.09708(9) 0.0233(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'
F F 0.0171 0.0103 '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
C6 C1 C2 118.2(3)
C6 C1 Br1 121.2(2)
C2 C1 Br1 120.6(2)
F1 C2 C3 119.1(3)
F1 C2 C1 120.2(3)
C3 C2 C1 120.7(3)
F2 C3 C4 120.0(3)
F2 C3 C2 118.8(3)
C4 C3 C2 121.1(3)
C3 C4 C5 118.5(3)
C3 C4 Br2 120.6(2)
C5 C4 Br2 120.8(2)
F3 C5 C6 118.9(3)
F3 C5 C4 120.7(2)
C6 C5 C4 120.4(3)
F4 C6 C5 119.1(3)
F4 C6 C1 119.9(2)
C5 C6 C1 121.0(3)
C8 C7 C12 118.3(3)
C8 C7 C20 123.0(3)
C12 C7 C20 118.7(3)
C9 C8 C7 121.0(3)
C9 C8 H8 119.5
C7 C8 H8 119.5
C8 C9 C10 121.0(3)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 119.0(3)
C11 C10 H10 120.5
C9 C10 H10 120.5
C10 C11 C12 121.3(3)
C10 C11 H11 119.4
C12 C11 H11 119.4
C11 C12 C7 119.4(3)
C11 C12 C13 121.0(3)
C7 C12 C13 119.6(3)
C14 C13 C12 121.5(3)
C14 C13 H13 119.2
C12 C13 H13 119.2
C13 C14 C15 121.3(3)
C13 C14 H14 119.4
C15 C14 H14 119.4
C16 C15 C20 118.7(3)
C16 C15 C14 121.4(3)
C20 C15 C14 119.9(3)
C17 C16 C15 121.7(3)
C17 C16 H16 119.1
C15 C16 H16 119.1
C16 C17 C18 119.3(3)
C16 C17 H17 120.4
C18 C17 H17 120.4
C19 C18 C17 121.0(3)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C20 120.8(3)
C18 C19 H19 119.6
C20 C19 H19 119.6
C19 C20 C15 118.6(3)
C19 C20 C7 122.5(3)
C15 C20 C7 118.9(3)
C22 C21 C26 120.0
C22 C21 C34 118.4(4)
C26 C21 C34 121.6(4)
C21 C22 C23 120.0
C21 C22 H22 120.0
C23 C22 H22 120.0
C24 C23 C22 120.0
C24 C23 H23 120.0
C22 C23 H23 120.0
C23 C24 C25 120.0
C23 C24 H24 120.0
C25 C24 H24 120.0
C24 C25 C26 120.0
C24 C25 H25 120.0
C26 C25 H25 120.0
C25 C26 C21 120.0
C25 C26 C27 120.4(4)
C21 C26 C27 119.6(4)
C28 C27 C26 121.9(5)
C28 C27 H27 119.1
C26 C27 H27 119.1
C27 C28 C29 119.2(6)
C27 C28 H28 120.4
C29 C28 H28 120.4
C30 C29 C34 120.0
C30 C29 C28 117.6(4)
C34 C29 C28 122.4(4)
C31 C30 C29 120.0
C31 C30 H30 120.0
C29 C30 H30 120.0
C30 C31 C32 120.0
C30 C31 H31 120.0
C32 C31 H31 120.0
C33 C32 C31 120.0
C33 C32 H32 120.0
C31 C32 H32 120.0
C34 C33 C32 120.0
C34 C33 H33 120.0
C32 C33 H33 120.0
C33 C34 C29 120.0
C33 C34 C21 124.7(4)
C29 C34 C21 115.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.870(3)
Br2 C4 1.867(3)
C1 C6 1.381(4)
C1 C2 1.386(4)
C2 F1 1.346(3)
C2 C3 1.374(4)
C3 F2 1.346(3)
C3 C4 1.373(4)
C4 C5 1.387(4)
C5 F3 1.332(3)
C5 C6 1.378(4)
C6 F4 1.341(3)
C7 C8 1.405(4)
C7 C12 1.418(4)
C7 C20 1.465(4)
C8 C9 1.367(4)
C8 H8 0.9500
C9 C10 1.407(4)
C9 H9 0.9500
C10 C11 1.366(4)
C10 H10 0.9500
C11 C12 1.411(4)
C11 H11 0.9500
C12 C13 1.431(4)
C13 C14 1.345(4)
C13 H13 0.9500
C14 C15 1.423(4)
C14 H14 0.9500
C15 C16 1.408(4)
C15 C20 1.419(4)
C16 C17 1.364(5)
C16 H16 0.9500
C17 C18 1.396(5)
C17 H17 0.9500
C18 C19 1.370(4)
C18 H18 0.9500
C19 C20 1.405(4)
C19 H19 0.9500
C21 C22 1.3900
C21 C26 1.3900
C21 C34 1.508(4)
C22 C23 1.3900
C22 H22 0.9500
C23 C24 1.3900
C23 H23 0.9500
C24 C25 1.3900
C24 H24 0.9500
C25 C26 1.3900
C25 H25 0.9500
C26 C27 1.398(4)
C27 C28 1.385(4)
C27 H27 0.9500
C28 C29 1.451(7)
C28 H28 0.9500
C29 C30 1.3900
C29 C34 1.3900
C30 C31 1.3900
C30 H30 0.9500
C31 C32 1.3900
C31 H31 0.9500
C32 C33 1.3900
C32 H32 0.9500
C33 C34 1.3900
C33 H33 0.9500
