#------------------------------------------------------------------------------
#$Date: 2015-09-05 23:34:09 +0300 (Sat, 05 Sep 2015) $
#$Revision: 154543 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/33/4513307.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_4513307
loop_
_publ_author_name
'Lusi, Matteo'
'Vitorica-Yrezabal, Inigo J.'
'Zaworotko, Michael J.'
_publ_section_title
;
 Expanding the Scope of Molecular Mixed Crystals Enabled by Three
 Component Solid Solutions
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4098
_journal_paper_doi               10.1021/acs.cgd.5b00685
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C13 H9 N'
_chemical_formula_weight         179.21
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 99.84(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.183(5)
_cell_length_b                   5.9341(12)
_cell_length_c                   13.590(4)
_cell_measurement_temperature    100(2)
_cell_volume                     888.6(5)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.844
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2815
_diffrn_reflns_av_unetI/netI     0.4495
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_min         3.043
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  2.24
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.000(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.4477
_refine_ls_R_factor_gt           0.2058
_refine_ls_shift/su_max          3.710
_refine_ls_shift/su_mean         0.062
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3984
_refine_ls_wR_factor_ref         0.5748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                342
_reflns_number_total             2034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00685_si_024.cif
_cod_data_source_block           C:\#23
_cod_depositor_comments
'Adding full bibliography for 4513301--4513322.cif.'
_cod_original_cell_volume        888.5(5)
_cod_database_code               4513307
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.9293(11) 0.7248(13) 0.3926(6) 0.051(4) Uani 1 1 d . .
C2 C 0.8693(14) 0.6539(15) 0.4616(9) 0.052(5) Uani 1 1 d . .
C3 C 0.8596(14) 0.7912(16) 0.5442(8) 0.055(5) Uani 1 1 d . .
H3 H 0.8996 0.9330 0.5504 0.065 Uiso 1 1 calc R U
C4 C 0.7947(15) 0.7280(18) 0.6157(8) 0.064(6) Uani 1 1 d . .
H4 H 0.7909 0.8256 0.6705 0.076 Uiso 1 1 calc R U
C5 C 0.7323(13) 0.5167(16) 0.6096(8) 0.054(5) Uani 1 1 d . .
H5 H 0.6847 0.4738 0.6581 0.064 Uiso 1 1 calc R U
C6 C 0.7438(14) 0.3785(16) 0.5307(9) 0.058(5) Uani 1 1 d . .
H6 H 0.7052 0.2355 0.5272 0.070 Uiso 1 1 calc R U
C7 C 0.8070(14) 0.4340(15) 0.4577(7) 0.053(5) Uani 1 1 d . .
C8 C 0.8219(13) 0.2967(16) 0.3738(8) 0.052(5) Uani 1 1 d . .
H8 H 0.7877 0.1498 0.3693 0.062 Uiso 1 1 calc R U
C9 C 0.8803(13) 0.3631(15) 0.3027(8) 0.047(4) Uani 1 1 d . .
C10 C 0.8950(13) 0.2394(15) 0.2160(7) 0.048(5) Uani 1 1 d . .
H10 H 0.8626 0.0912 0.2086 0.057 Uiso 1 1 calc R U
C11 C 0.9513(14) 0.3186(16) 0.1446(10) 0.075(7) Uani 1 1 d . .
H11 H 0.9541 0.2292 0.0871 0.091 Uiso 1 1 calc R U
C12 C 1.0082(12) 0.5371(15) 0.1526(8) 0.046(4) Uani 1 1 d . .
H12 H 1.0508 0.5951 0.1033 0.055 Uiso 1 1 calc R U
C13 C 0.9951(12) 0.6598(15) 0.2410(8) 0.035(4) Uani 1 1 d . .
H13 H 1.0314 0.8049 0.2488 0.043 Uiso 1 1 calc R U
C14 C 0.9363(13) 0.5895(15) 0.3145(8) 0.042(4) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C14 118.6(10)
N1 C2 C3 120.3(11)
N1 C2 C7 123.6(11)
C3 C2 C7 116.1(14)
C4 C3 C2 122.3(11)
C3 C4 C5 121.0(11)
C6 C5 C4 117.3(14)
C7 C6 C5 123.9(12)
C6 C7 C8 126.2(11)
C6 C7 C2 119.4(10)
C8 C7 C2 114.4(12)
C9 C8 C7 123.6(10)
C8 C9 C10 126.6(11)
C8 C9 C14 116.5(10)
C10 C9 C14 116.9(13)
C11 C10 C9 123.9(11)
C10 C11 C12 121.5(12)
C13 C12 C11 114.4(13)
C14 C13 C12 126.5(10)
N1 C14 C13 120.0(10)
N1 C14 C9 123.2(12)
C13 C14 C9 116.8(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.312(17)
N1 C14 1.343(12)
C2 C3 1.407(16)
C2 C7 1.476(15)
C3 C4 1.360(19)
C4 C5 1.431(16)
C5 C6 1.372(15)
C6 C7 1.354(19)
C7 C8 1.434(14)
C8 C9 1.316(19)
C9 C10 1.421(15)
C9 C14 1.479(15)
C10 C11 1.329(19)
C11 C12 1.440(14)
C12 C13 1.434(15)
C13 C14 1.352(16)
