#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:33:07 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180267 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/53/7115351.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_7115351
loop_
_publ_author_name
'Shinaj K. Rajagopal'
'Abbey M. Philip'
'Kalaivanan Nagarajan'
'Mahesh Hariharan'
_publ_section_title
;
 Progressive acylation of pyrene engineers solid state packing and colour
 via C-H...H-C, C-H...O and pi-pi interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8644
_journal_paper_doi               10.1039/C4cc01897D
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H14 O2'
_chemical_formula_sum            'C20 H14 O2'
_chemical_formula_weight         286.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3519(3)
_cell_length_b                   16.6654(9)
_cell_length_c                   11.3344(5)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.44
_cell_volume                     1388.72(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5744
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_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     106
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0427
_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)+(0.0597P)²+0.4997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                926
_reflns_number_total             1269
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4cc01897d2.cif
_cod_data_source_block           orthopb
_cod_original_sg_symbol_H-M      'Pnma '
_cod_database_code               7115351
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
C1 C 0.1119(3) 0.10257(12) 0.93578(17) 0.0562(6) Uani 1 1 d .
H1A H 0.0858 0.0517 0.9717 0.084 Uiso 1 1 calc R
H1B H 0.0510 0.1444 0.9786 0.084 Uiso 1 1 calc R
H1C H 0.2407 0.1119 0.9372 0.084 Uiso 1 1 calc R
C2 C 0.0464(3) 0.10214(11) 0.81030(16) 0.0456(5) Uani 1 1 d .
C3 C 0.0732(2) 0.17665(10) 0.73823(15) 0.0394(4) Uani 1 1 d .
C4 C 0.0652(3) 0.2500 0.7960(2) 0.0393(6) Uani 1 2 d S
H4 H 0.0540 0.2500 0.8778 0.047 Uiso 1 2 calc SR
C5 C 0.1004(2) 0.17537(10) 0.61470(15) 0.0382(4) Uani 1 1 d .
C6 C 0.1188(3) 0.10235(11) 0.54783(16) 0.0473(5) Uani 1 1 d .
H6 H 0.1110 0.0533 0.5866 0.057 Uiso 1 1 calc R
C7 C 0.1471(3) 0.10337(12) 0.43037(16) 0.0505(5) Uani 1 1 d .
H7 H 0.1562 0.0550 0.3900 0.061 Uiso 1 1 calc R
C8 C 0.1635(2) 0.17669(12) 0.36644(16) 0.0465(5) Uani 1 1 d .
C9 C 0.1489(3) 0.2500 0.4289(2) 0.0405(6) Uani 1 2 d S
C10 C 0.1176(3) 0.2500 0.5536(2) 0.0369(6) Uani 1 2 d S
C11 C 0.1930(3) 0.17816(14) 0.24444(18) 0.0595(6) Uani 1 1 d .
H11 H 0.2033 0.1302 0.2030 0.071 Uiso 1 1 calc R
C12 C 0.2068(4) 0.2500 0.1854(3) 0.0645(9) Uani 1 2 d S
H12 H 0.2258 0.2500 0.1042 0.077 Uiso 1 2 calc SR
O1 O -0.0303(2) 0.04354(8) 0.77058(13) 0.0706(5) 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'
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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 C3 121.66(17) . .
O1 C2 C1 120.26(17) . .
C3 C2 C1 118.04(16) . .
C4 C3 C5 119.10(16) . .
C4 C3 C2 117.82(16) . .
C5 C3 C2 123.05(15) . .
C3 C4 C3 123.4(2) . 8_565
C3 C4 H4 118.3 . .
C3 C4 H4 118.3 8_565 .
C3 C5 C10 118.63(16) . .
C3 C5 C6 123.17(16) . .
C10 C5 C6 118.16(16) . .
C7 C6 C5 121.59(17) . .
C7 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C6 C7 C8 121.73(17) . .
C6 C7 H7 119.1 . .
C8 C7 H7 119.1 . .
C11 C8 C9 119.36(19) . .
C11 C8 C7 122.02(18) . .
C9 C8 C7 118.62(17) . .
C8 C9 C8 119.3(2) . 8_565
C8 C9 C10 120.36(12) . .
C8 C9 C10 120.36(12) 8_565 .
C5 C10 C5 121.0(2) . 8_565
C5 C10 C9 119.51(11) . .
C5 C10 C9 119.51(11) 8_565 .
C12 C11 C8 120.5(2) . .
C12 C11 H11 119.7 . .
C8 C11 H11 119.7 . .
C11 C12 C11 121.0(3) . 8_565
C11 C12 H12 119.5 . .
C11 C12 H12 119.5 8_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.501(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 O1 1.214(2) .
C2 C3 1.499(2) .
C3 C4 1.388(2) .
C3 C5 1.415(2) .
C4 C3 1.388(2) 8_565
C4 H4 0.9300 .
C5 C10 1.429(2) .
C5 C6 1.440(2) .
C6 C7 1.348(3) .
C6 H6 0.9300 .
C7 C8 1.426(3) .
C7 H7 0.9300 .
C8 C11 1.400(3) .
C8 C9 1.416(2) .
C9 C8 1.416(2) 8_565
C9 C10 1.432(3) .
C10 C5 1.429(2) 8_565
C11 C12 1.376(2) .
C11 H11 0.9300 .
C12 C11 1.376(2) 8_565
C12 H12 0.9300 .
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_4
O1 C2 C3 C4 145.3(2) . .
C1 C2 C3 C4 -32.7(3) . .
O1 C2 C3 C5 -32.8(3) . .
C1 C2 C3 C5 149.25(18) . .
C5 C3 C4 C3 3.5(4) . 8_565
C2 C3 C4 C3 -174.65(16) . 8_565
C4 C3 C5 C10 -0.5(3) . .
C2 C3 C5 C10 177.60(17) . .
C4 C3 C5 C6 177.08(18) . .
C2 C3 C5 C6 -4.9(3) . .
C3 C5 C6 C7 -179.12(17) . .
C10 C5 C6 C7 -1.6(3) . .
C5 C6 C7 C8 1.1(3) . .
C6 C7 C8 C11 179.95(19) . .
C6 C7 C8 C9 -0.2(3) . .
C11 C8 C9 C8 0.4(3) . 8_565
C7 C8 C9 C8 -179.52(14) . 8_565
C11 C8 C9 C10 179.6(2) . .
C7 C8 C9 C10 -0.3(3) . .
C3 C5 C10 C5 -2.4(3) . 8_565
C6 C5 C10 C5 179.89(14) . 8_565
C3 C5 C10 C9 178.75(19) . .
C6 C5 C10 C9 1.1(3) . .
C8 C9 C10 C5 -0.2(3) . .
C8 C9 C10 C5 179.03(18) 8_565 .
C8 C9 C10 C5 -179.03(18) . 8_565
C8 C9 C10 C5 0.2(3) 8_565 8_565
C9 C8 C11 C12 -0.3(3) . .
C7 C8 C11 C12 179.5(2) . .
C8 C11 C12 C11 0.3(5) . 8_565
