#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205618.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_7205618
loop_
_publ_author_name
'Cao, Deng-Ke'
'Sreevidya, Thekku V.'
'Botoshansky, Mark'
'Golden, Gilad'
'Benedict, Jason B.'
'Kaftory, Menahem'
_publ_section_title
;
 Formation of different photodimers of isoquinolinone by irradiation of
 solid molecular compounds
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3181
_journal_paper_doi               10.1039/c0ce00489h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C30 H22 O2 , 2(C9 H7 N O)'
_chemical_formula_sum            'C48 H36 N2 O4'
_chemical_formula_weight         704.79
_chemical_name_systematic
;
1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol:2(Isoquinolin-3(2H)-one)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.4020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.1065(12)
_cell_length_b                   9.2347(4)
_cell_length_c                   16.4901(8)
_cell_measurement_reflns_used    2629
_cell_measurement_temperature    286(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.36
_cell_volume                     3728.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      286(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12369
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0416
_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)+(0.0517P)²+1.0497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                2565
_reflns_number_total             3828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00489h.txt
_cod_data_source_block           Cao5(prism)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7205618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.14426(4) 0.57596(13) 0.46580(8) 0.0517(3) Uani 1 1 d . . .
H1 H 0.1200 0.5626 0.4821 0.062 Uiso 1 1 calc R . .
O2 O 0.06725(5) 0.45649(12) 0.02482(9) 0.0572(3) Uani 1 1 d . . .
N1 N 0.00523(5) 0.32314(14) 0.05123(9) 0.0484(3) Uani 1 1 d . . .
H1N H -0.0165 0.3962 0.0335 0.058 Uiso 1 1 calc R . .
C1 C 0.02766(6) 0.50182(16) 0.27752(10) 0.0422(4) Uani 1 1 d . . .
C2 C 0.07546(6) 0.50050(16) 0.32539(10) 0.0425(4) Uani 1 1 d . . .
C3 C 0.13405(5) 0.49049(16) 0.38894(10) 0.0388(3) Uani 1 1 d . . .
C4 C 0.16956(6) 0.55059(16) 0.34501(10) 0.0386(3) Uani 1 1 d . . .
C5 C 0.20542(7) 0.66244(19) 0.38440(12) 0.0548(4) Uani 1 1 d . . .
H5 H 0.2075 0.7034 0.4373 0.066 Uiso 1 1 calc R . .
C6 C 0.23844(8) 0.7146(2) 0.34602(15) 0.0728(6) Uani 1 1 d . . .
H6 H 0.2627 0.7897 0.3737 0.087 Uiso 1 1 calc R . .
C7 C 0.23578(8) 0.6571(2) 0.26817(15) 0.0712(6) Uani 1 1 d . . .
H7 H 0.2581 0.6925 0.2427 0.085 Uiso 1 1 calc R . .
C8 C 0.19989(9) 0.5464(2) 0.22775(14) 0.0669(5) Uani 1 1 d . . .
H8 H 0.1977 0.5068 0.1744 0.080 Uiso 1 1 calc R . .
C9 C 0.16700(7) 0.4934(2) 0.26588(12) 0.0549(4) Uani 1 1 d . . .
H9 H 0.1428 0.4183 0.2379 0.066 Uiso 1 1 calc R . .
C10 C 0.14779(6) 0.33022(17) 0.41480(10) 0.0394(3) Uani 1 1 d . . .
C11 C 0.18418(7) 0.2939(2) 0.50160(11) 0.0539(4) Uani 1 1 d . . .
H11 H 0.2003 0.3665 0.5439 0.065 Uiso 1 1 calc R . .
C12 C 0.19670(8) 0.1504(2) 0.52572(14) 0.0703(6) Uani 1 1 d . . .
H12 H 0.2209 0.1273 0.5843 0.084 Uiso 1 1 calc R . .
C13 C 0.17406(9) 0.0431(2) 0.46486(17) 0.0747(6) Uani 1 1 d . . .
H13 H 0.1826 -0.0530 0.4819 0.090 Uiso 1 1 calc R . .
C14 C 0.13863(9) 0.0763(2) 0.37821(15) 0.0704(6) Uani 1 1 d . . .
H14 H 0.1236 0.0028 0.3362 0.084 Uiso 1 1 calc R . .
C15 C 0.12522(7) 0.21953(18) 0.35335(12) 0.0554(4) Uani 1 1 d . . .
H15 H 0.1008 0.2414 0.2947 0.066 Uiso 1 1 calc R . .
C16 C 0.05617(6) 0.33705(17) 0.05197(10) 0.0451(4) Uani 1 1 d . . .
C17 C 0.09038(7) 0.21748(18) 0.08265(11) 0.0498(4) Uani 1 1 d . . .
H17 H 0.1254 0.2224 0.0856 0.060 Uiso 1 1 calc R . .
C18 C 0.07370(7) 0.09056(17) 0.10913(10) 0.0477(4) Uani 1 1 d . . .
C19 C 0.10740(8) -0.0349(2) 0.13844(13) 0.0643(5) Uani 1 1 d . . .
H19 H 0.1426 -0.0335 0.1419 0.077 Uiso 1 1 calc R . .
C20 C 0.08808(10) -0.1567(2) 0.16134(15) 0.0764(6) Uani 1 1 d . . .
H20 H 0.1103 -0.2383 0.1796 0.092 Uiso 1 1 calc R . .
C21 C 0.03585(10) -0.1627(2) 0.15817(15) 0.0754(6) Uani 1 1 d . . .
H21 H 0.0239 -0.2475 0.1745 0.090 Uiso 1 1 calc R . .
C22 C 0.00246(9) -0.0462(2) 0.13155(13) 0.0656(5) Uani 1 1 d . . .
H22 H -0.0322 -0.0507 0.1299 0.079 Uiso 1 1 calc R . .
C23 C 0.02055(7) 0.08301(17) 0.10606(11) 0.0488(4) Uani 1 1 d . . .
C24 C -0.01242(7) 0.20427(18) 0.07606(12) 0.0528(4) Uani 1 1 d . . .
H24 H -0.0474 0.2026 0.0732 0.063 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
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 N1 C16 124.34(14) . . ?
C2 C1 C1 179.37(15) . 2 ?
C1 C2 C3 175.73(17) . . ?
O1 C3 C2 109.67(12) . . ?
O1 C3 C4 107.42(12) . . ?
C2 C3 C4 109.99(12) . . ?
O1 C3 C10 110.89(12) . . ?
C2 C3 C10 108.29(12) . . ?
C4 C3 C10 110.58(11) . . ?
C5 C4 C9 118.16(15) . . ?
C5 C4 C3 120.51(14) . . ?
C9 C4 C3 121.33(14) . . ?
C4 C5 C6 120.63(18) . . ?
C7 C6 C5 120.77(19) . . ?
C6 C7 C8 119.23(18) . . ?
C7 C8 C9 120.29(19) . . ?
C4 C9 C8 120.91(18) . . ?
C15 C10 C11 118.18(15) . . ?
C15 C10 C3 121.90(13) . . ?
C11 C10 C3 119.91(14) . . ?
C12 C11 C10 120.46(17) . . ?
C13 C12 C11 120.66(18) . . ?
C12 C13 C14 120.03(19) . . ?
C13 C14 C15 119.93(19) . . ?
C10 C15 C14 120.72(17) . . ?
O2 C16 N1 117.57(14) . . ?
O2 C16 C17 126.49(15) . . ?
N1 C16 C17 115.95(14) . . ?
C16 C17 C18 121.81(15) . . ?
C17 C18 C23 119.38(15) . . ?
C17 C18 C19 122.94(16) . . ?
C23 C18 C19 117.67(16) . . ?
C20 C19 C18 119.95(19) . . ?
C19 C20 C21 121.82(18) . . ?
C22 C21 C20 120.52(19) . . ?
C21 C22 C23 119.77(19) . . ?
C24 C23 C22 122.23(16) . . ?
C24 C23 C18 117.51(15) . . ?
C22 C23 C18 120.25(16) . . ?
N1 C24 C23 120.99(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.4160(17) . ?
O2 C16 1.2738(18) . ?
N1 C24 1.330(2) . ?
N1 C16 1.3816(19) . ?
C1 C2 1.1936(19) . ?
C1 C1 1.380(3) 2 ?
C2 C3 1.484(2) . ?
C3 C4 1.536(2) . ?
C3 C10 1.541(2) . ?
C4 C5 1.376(2) . ?
C4 C9 1.381(2) . ?
C5 C6 1.385(3) . ?
C6 C7 1.362(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.382(3) . ?
C10 C15 1.384(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.383(3) . ?
C12 C13 1.355(3) . ?
C13 C14 1.371(3) . ?
C14 C15 1.386(3) . ?
C16 C17 1.390(2) . ?
C17 C18 1.392(2) . ?
C18 C23 1.422(2) . ?
C18 C19 1.425(2) . ?
C19 C20 1.361(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.352(3) . ?
C22 C23 1.421(2) . ?
C23 C24 1.385(2) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 -24(22) 2 . . . ?
C1 C2 C3 O1 -82(2) . . . . ?
C1 C2 C3 C4 160(2) . . . . ?
C1 C2 C3 C10 39(2) . . . . ?
O1 C3 C4 C5 3.51(19) . . . . ?
C2 C3 C4 C5 122.82(15) . . . . ?
C10 C3 C4 C5 -117.63(15) . . . . ?
O1 C3 C4 C9 -177.26(14) . . . . ?
C2 C3 C4 C9 -57.95(19) . . . . ?
C10 C3 C4 C9 61.61(18) . . . . ?
C9 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 C6 178.47(16) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C8 0.5(2) . . . . ?
C3 C4 C9 C8 -178.74(15) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
O1 C3 C10 C15 157.78(14) . . . . ?
C2 C3 C10 C15 37.42(19) . . . . ?
C4 C3 C10 C15 -83.17(17) . . . . ?
O1 C3 C10 C11 -22.90(18) . . . . ?
C2 C3 C10 C11 -143.27(14) . . . . ?
C4 C3 C10 C11 96.15(16) . . . . ?
C15 C10 C11 C12 -0.9(2) . . . . ?
C3 C10 C11 C12 179.76(15) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C11 C10 C15 C14 0.2(3) . . . . ?
C3 C10 C15 C14 179.49(16) . . . . ?
C13 C14 C15 C10 0.9(3) . . . . ?
C24 N1 C16 O2 178.77(16) . . . . ?
C24 N1 C16 C17 -1.2(2) . . . . ?
O2 C16 C17 C18 -178.64(16) . . . . ?
N1 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C23 -0.9(2) . . . . ?
C16 C17 C18 C19 178.19(16) . . . . ?
C17 C18 C19 C20 -178.40(18) . . . . ?
C23 C18 C19 C20 0.7(3) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C24 178.30(18) . . . . ?
C21 C22 C23 C18 -0.5(3) . . . . ?
C17 C18 C23 C24 0.2(2) . . . . ?
C19 C18 C23 C24 -178.89(16) . . . . ?
C17 C18 C23 C22 179.08(16) . . . . ?
C19 C18 C23 C22 0.0(2) . . . . ?
C16 N1 C24 C23 0.6(3) . . . . ?
C22 C23 C24 N1 -178.91(16) . . . . ?
C18 C23 C24 N1 -0.1(3) . . . . ?
