#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:14:32 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180174 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/70/7107004.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_7107004
loop_
_publ_author_name
'Srinu Tothadi'
'Arijit Mukherjee'
'Gautam R. Desiraju'
_publ_section_title
;
 Shape and size mimicry in the design of ternary molecular solids: towards
 a robust strategy for crystal engineering
;
_journal_name_full               Chem.Commun.
_journal_page_first              12080
_journal_paper_doi               10.1039/c1cc14567c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C36 H32 N4 O4'
_chemical_formula_weight         584.66
_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                 125.572(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.6576(9)
_cell_length_b                   19.710(2)
_cell_length_c                   11.6365(12)
_cell_measurement_reflns_used    12950
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     1428.6(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'XtaLABmini: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14793
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0420
_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)+(0.0430P)²+0.5808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2732
_reflns_number_total             3280
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1cc14567c.txt
_cod_data_source_block           mres_bipy_phenazine
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7107004
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
N1 N 0.59943(19) -0.06409(6) 0.55706(12) 0.0243(3) Uani 1 1 d .
C1 C 0.6817(2) -0.00661(7) 0.63159(15) 0.0228(3) Uani 1 1 d .
C2 C 0.4177(2) -0.05817(7) 0.42559(14) 0.0224(3) Uani 1 1 d .
C3 C 0.3228(2) -0.11706(7) 0.34022(16) 0.0273(3) Uani 1 1 d .
H3 H 0.3866 -0.1602 0.3768 0.033 Uiso 1 1 calc R
C4 C 0.1418(2) -0.11181(7) 0.20698(16) 0.0292(3) Uani 1 1 d .
H4 H 0.0801 -0.1515 0.1507 0.035 Uiso 1 1 calc R
C5 C 0.0430(2) -0.04794(8) 0.15031(15) 0.0286(3) Uani 1 1 d .
H5 H -0.0836 -0.0455 0.0565 0.034 Uiso 1 1 calc R
C6 C 0.8737(2) -0.00966(7) 0.77229(15) 0.0271(3) Uani 1 1 d .
H6 H 0.9428 -0.0520 0.8114 0.033 Uiso 1 1 calc R
N3 N -0.41424(18) -0.08456(6) 0.18620(12) 0.0237(3) Uani 1 1 d .
C7 C -0.4169(2) -0.01759(7) 0.20134(15) 0.0271(3) Uani 1 1 d .
H7 H -0.5326 0.0076 0.1253 0.033 Uiso 1 1 calc R
C8 C -0.2607(2) 0.01737(7) 0.32148(14) 0.0248(3) Uani 1 1 d .
H8 H -0.2720 0.0651 0.3269 0.030 Uiso 1 1 calc R
C9 C -0.0871(2) -0.01753(6) 0.43433(13) 0.0173(3) Uani 1 1 d .
C10 C -0.0848(2) -0.08729(7) 0.41853(14) 0.0265(3) Uani 1 1 d .
H10 H 0.0295 -0.1138 0.4923 0.032 Uiso 1 1 calc R
C11 C -0.2492(2) -0.11809(7) 0.29511(15) 0.0291(3) Uani 1 1 d .
H11 H -0.2443 -0.1659 0.2875 0.035 Uiso 1 1 calc R
O1 O 0.27804(15) -0.15324(5) 0.95205(9) 0.0210(2) Uani 1 1 d .
H1O H 0.3864 -0.1307 1.0327 0.031 Uiso 1 1 d R
O2 O 0.10814(15) -0.24751(5) 0.52443(9) 0.0232(2) Uani 1 1 d .
H2O H 0.1729 -0.2754 0.4990 0.035 Uiso 1 1 d R
C12 C -0.0384(2) -0.20937(7) 0.68737(14) 0.0222(3) Uani 1 1 d .
H12A H -0.0436 -0.2417 0.7493 0.033 Uiso 1 1 calc R
H12B H -0.1237 -0.2268 0.5904 0.033 Uiso 1 1 calc R
H12C H -0.0972 -0.1657 0.6899 0.033 Uiso 1 1 calc R
C13 C 0.1913(2) -0.19998(6) 0.73731(13) 0.0168(3) Uani 1 1 d .
C14 C 0.2596(2) -0.21933(6) 0.65375(13) 0.0184(3) Uani 1 1 d .
C15 C 0.4690(2) -0.20860(7) 0.69688(14) 0.0230(3) Uani 1 1 d .
H15 H 0.5108 -0.2208 0.6371 0.028 Uiso 1 1 calc R
C16 C 0.6159(2) -0.17988(7) 0.82794(15) 0.0254(3) Uani 1 1 d .
H16 H 0.7596 -0.1727 0.8583 0.030 Uiso 1 1 calc R
C17 C 0.5562(2) -0.16145(7) 0.91525(14) 0.0219(3) Uani 1 1 d .
H17 H 0.6585 -0.1424 1.0056 0.026 Uiso 1 1 calc R
C18 C 0.3449(2) -0.17114(6) 0.86927(13) 0.0171(3) 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'
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
C1 N1 C2 116.61(12) . .
N1 C1 C6 119.24(13) . .
N1 C1 C2 121.91(13) . 3_656
C6 C1 C2 118.85(12) . 3_656
N1 C2 C3 119.56(13) . .
N1 C2 C1 121.48(12) . 3_656
C3 C2 C1 118.96(13) . 3_656
C4 C3 C2 120.27(13) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 120.91(14) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C6 C5 C4 121.12(14) 3_656 .
C6 C5 H5 119.4 3_656 .
C4 C5 H5 119.4 . .
C5 C6 C1 119.89(13) 3_656 .
C5 C6 H6 120.1 3_656 .
C1 C6 H6 120.1 . .
C11 N3 C7 116.35(12) . .
N3 C7 C8 123.77(13) . .
N3 C7 H7 118.1 . .
C8 C7 H7 118.1 . .
C7 C8 C9 119.83(13) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C10 C9 C8 116.33(12) . .
C10 C9 C9 121.46(14) . 3_556
C8 C9 C9 122.20(14) . 3_556
C11 C10 C9 119.87(13) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
N3 C11 C10 123.83(13) . .
N3 C11 H11 118.1 . .
C10 C11 H11 118.1 . .
C18 O1 H1O 110.7 . .
C14 O2 H2O 109.4 . .
C13 C12 H12A 109.5 . .
C13 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C13 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C18 117.22(11) . .
C14 C13 C12 121.50(11) . .
C18 C13 C12 121.27(11) . .
O2 C14 C15 121.25(12) . .
O2 C14 C13 116.91(11) . .
C15 C14 C13 121.80(12) . .
C16 C15 C14 119.20(12) . .
C16 C15 H15 120.4 . .
C14 C15 H15 120.4 . .
C15 C16 C17 120.83(12) . .
C15 C16 H16 119.6 . .
C17 C16 H16 119.6 . .
C16 C17 C18 119.28(12) . .
C16 C17 H17 120.4 . .
C18 C17 H17 120.4 . .
O1 C18 C17 121.31(12) . .
O1 C18 C13 117.06(11) . .
C17 C18 C13 121.63(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3404(18) .
N1 C2 1.3467(18) .
C1 C6 1.430(2) .
C1 C2 1.4363(19) 3_656
C2 C3 1.4220(19) .
C2 C1 1.4363(19) 3_656
C3 C4 1.355(2) .
C3 H3 0.9500 .
C4 C5 1.418(2) .
C4 H4 0.9500 .
C5 C6 1.356(2) 3_656
C5 H5 0.9500 .
C6 C5 1.356(2) 3_656
C6 H6 0.9500 .
N3 C11 1.3327(19) .
N3 C7 1.3335(18) .
C7 C8 1.3836(19) .
C7 H7 0.9500 .
C8 C9 1.3903(18) .
C8 H8 0.9500 .
C9 C10 1.3886(18) .
C9 C9 1.490(2) 3_556
C10 C11 1.3829(19) .
C10 H10 0.9500 .
C11 H11 0.9500 .
O1 C18 1.3742(15) .
O1 H1O 0.9277 .
O2 C14 1.3740(15) .
O2 H2O 0.8982 .
C12 C13 1.5092(18) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.3988(18) .
C13 C18 1.4010(18) .
C14 C15 1.3894(19) .
C15 C16 1.384(2) .
C15 H15 0.9500 .
C16 C17 1.3833(19) .
C16 H16 0.9500 .
C17 C18 1.3908(18) .
C17 H17 0.9500 .
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
C2 N1 C1 C6 179.57(12) . .
C2 N1 C1 C2 -0.3(2) . 3_656
C1 N1 C2 C3 179.45(12) . .
C1 N1 C2 C1 0.3(2) . 3_656
N1 C2 C3 C4 -179.01(13) . .
C1 C2 C3 C4 0.2(2) 3_656 .
C2 C3 C4 C5 -0.3(2) . .
C3 C4 C5 C6 -0.2(2) . 3_656
N1 C1 C6 C5 -179.01(13) . 3_656
C2 C1 C6 C5 0.9(2) 3_656 3_656
C11 N3 C7 C8 -0.1(2) . .
N3 C7 C8 C9 0.9(2) . .
C7 C8 C9 C10 -0.9(2) . .
C7 C8 C9 C9 179.27(15) . 3_556
C8 C9 C10 C11 0.2(2) . .
C9 C9 C10 C11 -179.97(15) 3_556 .
C7 N3 C11 C10 -0.7(2) . .
C9 C10 C11 N3 0.6(2) . .
C18 C13 C14 O2 -179.93(10) . .
C12 C13 C14 O2 -0.24(17) . .
C18 C13 C14 C15 -2.05(18) . .
C12 C13 C14 C15 177.65(12) . .
O2 C14 C15 C16 179.81(12) . .
C13 C14 C15 C16 2.0(2) . .
C14 C15 C16 C17 -0.5(2) . .
C15 C16 C17 C18 -0.9(2) . .
C16 C17 C18 O1 -179.62(12) . .
C16 C17 C18 C13 0.86(19) . .
C14 C13 C18 O1 -178.94(10) . .
C12 C13 C18 O1 1.36(17) . .
C14 C13 C18 C17 0.60(18) . .
C12 C13 C18 C17 -179.10(12) . .
