#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/68/2236862.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_2236862
loop_
_publ_author_name
'Nayak, Prakash S.'
'Narayana, Badiadka'
'Yathirajan, Hemmige S.'
'Gerber, Thomas'
'Hosten, Eric'
'Betz, Richard'
_publ_section_title
;
 [3-Benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone
;
_journal_coeditor_code           FJ2603
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3272
_journal_page_last               o3273
_journal_paper_doi               10.1107/S1600536812044650
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C30 H22 N2 O6'
_chemical_formula_moiety         'C30 H22 N2 O6'
_chemical_formula_sum            'C30 H22 N2 O6'
_chemical_formula_weight         506.50
_chemical_melting_point_gt       523
_chemical_name_common
;
1,1'-[2,4-Bis(3-nitrophenyl)cyclobutane-1,3-diyl]diphenylmethanone
;
_chemical_name_systematic
;
[3-Benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone
;
_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                 104.8580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.78500(10)
_cell_length_b                   14.7824(3)
_cell_length_c                   14.3589(3)
_cell_measurement_reflns_used    4849
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.76
_cell_volume                     1186.86(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11005
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0399
_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)+(0.0550P)²+0.3935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2387
_reflns_number_total             2945
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2603.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236862
_cod_database_fobs_code          2236862
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_symmetry_multiplicity
O O1 0.02716(16) 0.08341(7) 0.41101(7) 0.0343(2) Uani d . 1 1
O O2 0.4112(3) 0.11125(12) 0.89447(9) 0.0693(4) Uani d . 1 1
O O3 0.6594(3) 0.21980(8) 0.94461(8) 0.0584(4) Uani d . 1 1
N N1 0.5674(2) 0.16321(9) 0.88471(8) 0.0386(3) Uani d . 1 1
C C1 0.2098(2) 0.07918(8) 0.38436(8) 0.0223(2) Uani d . 1 1
C C2 0.4494(2) 0.05901(8) 0.45303(8) 0.0206(2) Uani d . 1 1
H H2 0.5684 0.1074 0.4506 0.025 Uiso calc R 1 1
C C3 0.44539(19) 0.03813(8) 0.55776(8) 0.0203(2) Uani d . 1 1
H H3 0.2767 0.0331 0.5629 0.024 Uiso calc R 1 1
C C11 0.2032(2) 0.09061(8) 0.28021(8) 0.0224(2) Uani d . 1 1
C C12 0.3971(2) 0.12395(9) 0.24994(9) 0.0266(3) Uani d . 1 1
H H12 0.5414 0.1391 0.2960 0.032 Uiso calc R 1 1
C C13 0.3792(2) 0.13495(10) 0.15237(9) 0.0333(3) Uani d . 1 1
H H13 0.5096 0.1596 0.1318 0.040 Uiso calc R 1 1
C C14 0.1718(3) 0.11009(11) 0.08487(10) 0.0371(3) Uani d . 1 1
H H14 0.1607 0.1173 0.0181 0.045 Uiso calc R 1 1
C C15 -0.0192(2) 0.07487(10) 0.11440(9) 0.0358(3) Uani d . 1 1
H H15 -0.1599 0.0565 0.0680 0.043 Uiso calc R 1 1
C C16 -0.0049(2) 0.06645(9) 0.21178(9) 0.0287(3) Uani d . 1 1
H H16 -0.1381 0.0440 0.2320 0.034 Uiso calc R 1 1
C C21 0.5883(2) 0.09762(8) 0.63665(8) 0.0209(2) Uani d . 1 1
C C22 0.5151(2) 0.10549(8) 0.72138(8) 0.0245(2) Uani d . 1 1
H H22 0.3736 0.0762 0.7275 0.029 Uiso calc R 1 1
C C23 0.6502(2) 0.15632(8) 0.79654(9) 0.0276(3) Uani d . 1 1
C C24 0.8559(2) 0.20118(9) 0.79156(9) 0.0319(3) Uani d . 1 1
H H24 0.9447 0.2362 0.8441 0.038 Uiso calc R 1 1
C C25 0.9279(2) 0.19330(9) 0.70728(10) 0.0307(3) Uani d . 1 1
H H25 1.0684 0.2235 0.7015 0.037 Uiso calc R 1 1
C C26 0.7973(2) 0.14165(8) 0.63095(9) 0.0254(2) Uani d . 1 1
H H26 0.8512 0.1363 0.5740 0.030 Uiso calc R 1 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O3 N1 O2 . . 123.53(13)
O3 N1 C23 . . 118.42(13)
O2 N1 C23 . . 118.05(12)
O1 C1 C11 . . 120.53(10)
O1 C1 C2 . . 122.11(10)
C11 C1 C2 . . 117.32(10)
C1 C2 C3 . . 115.82(9)
C1 C2 C3 . 3_656 115.26(9)
C3 C2 C3 . 3_656 90.93(8)
C1 C2 H2 . . 111.1
C3 C2 H2 . . 111.1
C3 C2 H2 3_656 . 111.1
C21 C3 C2 . . 118.37(9)
C21 C3 C2 . 3_656 116.97(9)
C2 C3 C2 . 3_656 89.07(8)
C21 C3 H3 . . 110.3
C2 C3 H3 . . 110.3
C2 C3 H3 3_656 . 110.3
C16 C11 C12 . . 119.38(11)
C16 C11 C1 . . 118.23(11)
C12 C11 C1 . . 122.39(10)
C13 C12 C11 . . 119.94(11)
C13 C12 H12 . . 120.0
C11 C12 H12 . . 120.0
C14 C13 C12 . . 120.16(12)
C14 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
C15 C14 C13 . . 120.16(12)
C15 C14 H14 . . 119.9
C13 C14 H14 . . 119.9
C14 C15 C16 . . 119.85(12)
C14 C15 H15 . . 120.1
C16 C15 H15 . . 120.1
C15 C16 C11 . . 120.46(12)
C15 C16 H16 . . 119.8
C11 C16 H16 . . 119.8
C22 C21 C26 . . 118.37(10)
C22 C21 C3 . . 118.42(10)
C26 C21 C3 . . 123.13(10)
C23 C22 C21 . . 119.39(12)
C23 C22 H22 . . 120.3
C21 C22 H22 . . 120.3
C24 C23 C22 . . 122.92(12)
C24 C23 N1 . . 119.20(11)
C22 C23 N1 . . 117.87(12)
C23 C24 C25 . . 117.54(11)
C23 C24 H24 . . 121.2
C25 C24 H24 . . 121.2
C24 C25 C26 . . 120.79(12)
C24 C25 H25 . . 119.6
C26 C25 H25 . . 119.6
C25 C26 C21 . . 120.99(11)
C25 C26 H26 . . 119.5
C21 C26 H26 . . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2141(15)
O2 N1 . 1.2210(19)
O3 N1 . 1.2199(16)
N1 C23 . 1.4676(17)
C1 C11 . 1.4957(16)
C1 C2 . 1.5104(15)
C2 C3 . 1.5412(15)
C2 C3 3_656 1.5827(16)
C2 H2 . 1.0000
C3 C21 . 1.5032(15)
C3 C2 3_656 1.5827(16)
C3 H3 . 1.0000
C11 C16 . 1.3910(16)
C11 C12 . 1.3931(17)
C12 C13 . 1.3877(17)
C12 H12 . 0.9500
C13 C14 . 1.385(2)
C13 H13 . 0.9500
C14 C15 . 1.383(2)
C14 H14 . 0.9500
C15 C16 . 1.3850(18)
C15 H15 . 0.9500
C16 H16 . 0.9500
C21 C22 . 1.3917(16)
C21 C26 . 1.3938(17)
C22 C23 . 1.3810(17)
C22 H22 . 0.9500
C23 C24 . 1.380(2)
C24 C25 . 1.382(2)
C24 H24 . 0.9500
C25 C26 . 1.3895(17)
C25 H25 . 0.9500
C26 H26 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C3 H3 O1 . 1.00 2.40 2.8509(14) 106 ?
C3 H3 O1 3_556 1.00 2.56 3.3957(15) 141 y
C14 H14 O2 1_554 0.95 2.56 3.3666(19) 142 y
C2 H2 O3 4_565 1.00 2.61 3.5009(17) 148 y
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 C1 C2 C3 . . 3.75(16)
C11 C1 C2 C3 . . -174.02(9)
O1 C1 C2 C3 . 3_656 108.12(13)
C11 C1 C2 C3 . 3_656 -69.65(13)
C1 C2 C3 C21 . . -120.73(11)
C3 C2 C3 C21 3_656 . 120.45(11)
C1 C2 C3 C2 . 3_656 118.82(11)
C3 C2 C3 C2 3_656 3_656 0.0
O1 C1 C11 C16 . . -28.05(17)
C2 C1 C11 C16 . . 149.76(11)
O1 C1 C11 C12 . . 152.23(12)
C2 C1 C11 C12 . . -29.96(16)
C16 C11 C12 C13 . . 1.65(18)
C1 C11 C12 C13 . . -178.63(12)
C11 C12 C13 C14 . . -2.1(2)
C12 C13 C14 C15 . . 0.5(2)
C13 C14 C15 C16 . . 1.5(2)
C14 C15 C16 C11 . . -2.0(2)
C12 C11 C16 C15 . . 0.39(19)
C1 C11 C16 C15 . . -179.34(12)
C2 C3 C21 C22 . . 153.77(10)
C2 C3 C21 C22 3_656 . -101.51(12)
C2 C3 C21 C26 . . -29.57(16)
C2 C3 C21 C26 3_656 . 75.16(14)
C26 C21 C22 C23 . . 0.10(17)
C3 C21 C22 C23 . . 176.93(11)
C21 C22 C23 C24 . . 0.70(19)
C21 C22 C23 N1 . . 179.91(11)
O3 N1 C23 C24 . . 11.86(19)
O2 N1 C23 C24 . . -167.48(14)
O3 N1 C23 C22 . . -167.39(13)
O2 N1 C23 C22 . . 13.3(2)
C22 C23 C24 C25 . . -0.62(19)
N1 C23 C24 C25 . . -179.82(12)
C23 C24 C25 C26 . . -0.24(19)
C24 C25 C26 C21 . . 1.03(19)
C22 C21 C26 C25 . . -0.94(18)
C3 C21 C26 C25 . . -177.61(11)
