#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:41:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180350 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/19/7201943.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_7201943
loop_
_publ_author_name
'Shin, Ji-Young'
'Patrick, Brian O.'
'Dolphin, David'
_publ_section_title
;
 Conformational flexibility of dipyrromethenes: supramolecular
 assemblies with hydroquinones
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              960
_journal_paper_doi               10.1039/b800367j
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C15 H11 N3 O2'
_chemical_formula_weight         265.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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            8
_cell_length_a                   14.6809(16)
_cell_length_b                   7.4146(9)
_cell_length_c                   24.350(3)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.97
_cell_measurement_theta_min      3.19
_cell_volume                     2650.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            54647
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0403
_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)+(0.0512P)²+0.5503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2243
_reflns_number_total             3122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b800367j.txt
_cod_data_source_block           Compound1
_cod_original_cell_volume        2650.6(6)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7201943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34074(10) 0.2034(2) 0.13516(6) 0.0519(4) Uani 1 1 d . . .
H1 H 0.3071 0.0973 0.1434 0.062 Uiso 1 1 calc R . .
C2 C 0.31679(11) 0.3320(2) 0.09683(6) 0.0536(4) Uani 1 1 d . . .
H2 H 0.2641 0.3302 0.0742 0.064 Uiso 1 1 calc R . .
C3 C 0.38429(10) 0.4659(2) 0.09730(5) 0.0477(3) Uani 1 1 d . . .
H3 H 0.3855 0.5715 0.0752 0.057 Uiso 1 1 calc R . .
C4 C 0.44968(9) 0.41526(17) 0.13644(5) 0.0391(3) Uani 1 1 d . . .
C5 C 0.53293(9) 0.50252(16) 0.15289(5) 0.0368(3) Uani 1 1 d . . .
C6 C 0.58779(9) 0.44213(17) 0.19552(5) 0.0380(3) Uani 1 1 d . . .
C7 C 0.67783(10) 0.50415(18) 0.21050(5) 0.0435(3) Uani 1 1 d . . .
H7 H 0.7109 0.5998 0.1939 0.052 Uiso 1 1 calc R . .
C8 C 0.70580(10) 0.3988(2) 0.25291(6) 0.0498(4) Uani 1 1 d . . .
H8 H 0.7624 0.4057 0.2717 0.060 Uiso 1 1 calc R . .
C9 C 0.63284(11) 0.2748(2) 0.26370(5) 0.0504(4) Uani 1 1 d . . .
H9 H 0.6346 0.1865 0.2920 0.060 Uiso 1 1 calc R . .
C10 C 0.56087(9) 0.66819(17) 0.12200(5) 0.0378(3) Uani 1 1 d . . .
C11 C 0.57832(9) 0.82897(17) 0.15038(5) 0.0427(3) Uani 1 1 d . . .
H11 H 0.5713 0.8324 0.1891 0.051 Uiso 1 1 calc R . .
C12 C 0.60580(10) 0.98379(18) 0.12253(6) 0.0496(4) Uani 1 1 d . . .
H12 H 0.6188 1.0921 0.1418 0.059 Uiso 1 1 calc R . .
C13 C 0.61371(10) 0.9754(2) 0.06582(6) 0.0516(4) Uani 1 1 d . . .
C14 C 0.59651(11) 0.8195(2) 0.03618(6) 0.0537(4) Uani 1 1 d . . .
H14 H 0.6025 0.8182 -0.0027 0.064 Uiso 1 1 calc R . .
C15 C 0.57040(10) 0.6653(2) 0.06443(5) 0.0465(3) Uani 1 1 d . . .
H15 H 0.5589 0.5569 0.0448 0.056 Uiso 1 1 calc R . .
N1 N 0.42022(8) 0.25340(16) 0.15914(5) 0.0448(3) Uani 1 1 d . . .
N2 N 0.56307(8) 0.29641(15) 0.23023(4) 0.0451(3) Uani 1 1 d . . .
N3 N 0.64200(11) 1.1402(2) 0.03623(8) 0.0759(5) Uani 1 1 d . . .
O1 O 0.67250(13) 1.2687(2) 0.06305(8) 0.1067(6) Uani 1 1 d . . .
O2 O 0.63308(11) 1.1408(2) -0.01446(7) 0.1018(6) Uani 1 1 d . . .
H1N H 0.4498(12) 0.199(2) 0.1880(7) 0.068(5) Uiso 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
_geom_angle_publ_flag
N1 C1 C2 108.74(13) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.68(13) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
C2 C3 C4 107.41(13) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 106.75(12) . . ?
N1 C4 C5 122.78(12) . . ?
C3 C4 C5 130.47(12) . . ?
C6 C5 C4 123.76(12) . . ?
C6 C5 C10 118.76(12) . . ?
C4 C5 C10 117.48(11) . . ?
C5 C6 N2 122.86(12) . . ?
C5 C6 C7 128.05(12) . . ?
N2 C6 C7 109.01(11) . . ?
C8 C7 C6 106.56(12) . . ?
C8 C7 H7 126.7 . . ?
C6 C7 H7 126.7 . . ?
C7 C8 C9 106.37(13) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C8 112.86(12) . . ?
N2 C9 H9 123.6 . . ?
C8 C9 H9 123.6 . . ?
C11 C10 C15 119.05(12) . . ?
C11 C10 C5 120.01(10) . . ?
C15 C10 C5 120.95(12) . . ?
C12 C11 C10 120.92(12) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 118.16(13) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C14 C13 C12 122.73(13) . . ?
C14 C13 N3 119.12(14) . . ?
C12 C13 N3 118.15(15) . . ?
C13 C14 C15 118.63(13) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 120.50(13) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C1 N1 C4 109.41(12) . . ?
C1 N1 H1N 127.8(11) . . ?
C4 N1 H1N 122.6(11) . . ?
C9 N2 C6 105.19(12) . . ?
O1 N3 O2 124.02(16) . . ?
O1 N3 C13 118.70(17) . . ?
O2 N3 C13 117.28(19) . . ?
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
C1 N1 1.357(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4039(19) . ?
C3 H3 0.9500 . ?
C4 N1 1.3903(17) . ?
C4 C5 1.4397(19) . ?
C5 C6 1.3882(18) . ?
C5 C10 1.4977(17) . ?
C6 N2 1.4190(16) . ?
C6 C7 1.446(2) . ?
C7 C8 1.3585(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.3186(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4015(18) . ?
C10 C15 1.4090(18) . ?
C11 C12 1.3930(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 N3 1.4781(19) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 H1N 0.920(18) . ?
N3 O1 1.239(2) . ?
N3 O2 1.241(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
N1 C1 C2 C3 0.07(16) . . . . ?
C1 C2 C3 C4 0.30(16) . . . . ?
C2 C3 C4 N1 -0.55(15) . . . . ?
C2 C3 C4 C5 179.24(13) . . . . ?
N1 C4 C5 C6 -5.23(19) . . . . ?
C3 C4 C5 C6 175.02(13) . . . . ?
N1 C4 C5 C10 175.02(11) . . . . ?
C3 C4 C5 C10 -4.73(19) . . . . ?
C4 C5 C6 N2 -5.49(19) . . . . ?
C10 C5 C6 N2 174.25(10) . . . . ?
C4 C5 C6 C7 170.87(12) . . . . ?
C10 C5 C6 C7 -9.38(19) . . . . ?
C5 C6 C7 C8 -176.88(13) . . . . ?
N2 C6 C7 C8 -0.11(14) . . . . ?
C6 C7 C8 C9 -0.39(15) . . . . ?
C7 C8 C9 N2 0.82(17) . . . . ?
C6 C5 C10 C11 -54.47(17) . . . . ?
C4 C5 C10 C11 125.29(13) . . . . ?
C6 C5 C10 C15 125.26(13) . . . . ?
C4 C5 C10 C15 -54.98(16) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C5 C10 C11 C12 178.96(12) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C11 C12 C13 N3 179.42(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
N3 C13 C14 C15 179.69(14) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C5 C10 C15 C14 -179.88(13) . . . . ?
C2 C1 N1 C4 -0.42(15) . . . . ?
C3 C4 N1 C1 0.60(14) . . . . ?
C5 C4 N1 C1 -179.20(12) . . . . ?
C8 C9 N2 C6 -0.86(16) . . . . ?
C5 C6 N2 C9 177.57(12) . . . . ?
C7 C6 N2 C9 0.59(14) . . . . ?
C14 C13 N3 O1 -167.49(16) . . . . ?
C12 C13 N3 O1 12.3(2) . . . . ?
C14 C13 N3 O2 12.8(2) . . . . ?
C12 C13 N3 O2 -167.37(15) . . . . ?
