#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:36:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180189 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/85/7108576.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_7108576
loop_
_publ_author_name
'Daniel P. Iwaniuk'
'Christian Wolf'
_publ_section_title
;
 Chiroptical sensing of citronellal: systematic development of a
 stereodynamic probe using the concept of isostericity
;
_journal_name_full               Chem.Commun.
_journal_page_first              11226
_journal_paper_doi               10.1039/c2cc36267h
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C38 H24 N2'
_chemical_formula_weight         508.59
_chemical_name_common            ICD-6
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.3450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8279(11)
_cell_length_b                   4.9456(6)
_cell_length_c                   27.487(3)
_cell_measurement_reflns_used    11300
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.910
_cell_measurement_theta_min      4.573
_cell_volume                     1327.8(3)
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_collection       'APEX, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_molecular_graphics    X-SEED,L.Barbour(1999):http://x-seed.net/
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Siemens SMART,Bruker APEXII CCD'
_diffrn_measurement_method       'omega 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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11300
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS.G.Sheldrick(1999)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1165
_reflns_number_gt                2598
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36267h.txt
_cod_data_source_block           c:\desktop\icd_6_wt\try_02
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7108576
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
N1 N 0.86124(11) -0.0879(2) 0.06821(4) 0.0271(3) Uani 1 1 d
C1 C 0.50517(12) 0.0920(2) 0.16844(4) 0.0178(2) Uani 1 1 d
C2 C 0.38524(12) 0.0855(2) 0.19179(4) 0.0217(3) Uani 1 1 d
C3 C 0.37324(13) 0.2446(3) 0.23262(4) 0.0233(3) Uani 1 1 d
C4 C 0.47977(13) 0.4145(3) 0.25083(4) 0.0240(3) Uani 1 1 d
C5 C 0.59930(12) 0.4234(2) 0.22829(4) 0.0225(3) Uani 1 1 d
C6 C 0.61395(11) 0.2624(2) 0.18724(4) 0.0186(2) Uani 1 1 d
C7 C 0.73816(12) 0.2702(2) 0.16442(4) 0.0203(2) Uani 1 1 d
C8 C 0.84244(12) 0.2774(2) 0.14548(4) 0.0212(3) Uani 1 1 d
C9 C 0.96248(11) 0.2719(2) 0.12040(4) 0.0200(2) Uani 1 1 d
C10 C 0.97066(12) 0.0808(2) 0.08263(4) 0.0206(3) Uani 1 1 d
C11 C 1.08963(13) 0.0761(3) 0.05871(5) 0.0246(3) Uani 1 1 d
C12 C 1.19518(13) 0.2569(3) 0.07104(5) 0.0254(3) Uani 1 1 d
C13 C 1.18656(13) 0.4471(3) 0.10776(5) 0.0265(3) Uani 1 1 d
C14 C 1.07148(13) 0.4532(3) 0.13244(5) 0.0247(3) Uani 1 1 d
C15 C 0.51394(11) -0.0687(2) 0.12540(4) 0.0188(2) Uani 1 1 d
C16 C 0.51344(11) -0.2006(2) 0.08871(4) 0.0191(2) Uani 1 1 d
C17 C 0.50713(11) -0.3524(2) 0.04377(4) 0.0178(2) Uani 1 1 d
C18 C 0.60001(12) -0.5619(2) 0.03819(4) 0.0196(2) Uani 1 1 d
C19 C 0.40680(12) -0.2925(2) 0.00496(4) 0.0198(2) Uani 1 1 d
H1 H 0.6707(15) -0.610(3) 0.0648(5) 0.027(4) Uiso 1 1 d
H2 H 0.6714(15) 0.541(3) 0.2403(5) 0.026(4) Uiso 1 1 d
H3 H 1.0615(14) 0.581(3) 0.1581(5) 0.026(4) Uiso 1 1 d
H4 H 1.2804(15) 0.250(3) 0.0539(5) 0.030(4) Uiso 1 1 d
H5 H 0.2889(14) 0.236(3) 0.2491(5) 0.027(4) Uiso 1 1 d
H6 H 0.3397(14) -0.153(3) 0.0081(5) 0.027(4) Uiso 1 1 d
H7 H 1.0942(15) -0.063(3) 0.0328(5) 0.031(4) Uiso 1 1 d
H8 H 0.4711(14) 0.525(3) 0.2795(5) 0.026(4) Uiso 1 1 d
H9 H 0.3095(15) -0.031(3) 0.1780(5) 0.026(4) Uiso 1 1 d
H10 H 1.2625(17) 0.578(3) 0.1158(6) 0.041(4) Uiso 1 1 d
H11 H 0.7963(17) -0.114(3) 0.0903(6) 0.041(4) Uiso 1 1 d
H12 H 0.882(2) -0.245(4) 0.0514(7) 0.058(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'
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
C2 C1 C6 119.07(10) .
C2 C1 C15 119.62(10) .
C6 C1 C15 121.29(10) .
C3 C2 C1 120.55(11) .
C2 C3 C4 120.39(11) .
C5 C4 C3 119.92(11) .
C4 C5 C6 120.58(11) .
C5 C6 C1 119.48(10) .
C5 C6 C7 120.34(10) .
C1 C6 C7 120.17(10) .
C8 C7 C6 179.73(13) .
C7 C8 C9 175.86(12) .
C14 C9 C10 119.68(11) .
C14 C9 C8 121.39(11) .
C10 C9 C8 118.92(10) .
N1 C10 C11 121.14(11) .
N1 C10 C9 120.55(11) .
C11 C10 C9 118.24(11) .
C12 C11 C10 121.04(12) .
C11 C12 C13 120.77(12) .
C14 C13 C12 119.37(11) .
C13 C14 C9 120.88(12) .
C16 C15 C1 176.25(12) .
C15 C16 C17 177.35(12) .
C18 C17 C19 119.02(10) .
C18 C17 C16 120.83(10) .
C19 C17 C16 120.15(10) .
C19 C18 C17 120.58(10) 3_645
C18 C19 C17 120.40(11) 3_645
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C10 1.3838(16) .
C1 C2 1.4033(16) .
C1 C6 1.4136(16) .
C1 C15 1.4357(15) .
C2 C3 1.3863(16) .
C3 C4 1.3916(18) .
C4 C5 1.3880(17) .
C5 C6 1.4013(16) .
C6 C7 1.4332(16) .
C7 C8 1.2002(17) .
C8 C9 1.4310(16) .
C9 C14 1.4082(17) .
C9 C10 1.4128(17) .
C10 C11 1.4035(17) .
C11 C12 1.3832(18) .
C12 C13 1.3889(18) .
C13 C14 1.3820(17) .
C15 C16 1.2005(16) .
C16 C17 1.4409(15) .
C17 C18 1.4007(16) .
C17 C19 1.4019(16) .
C18 C19 1.3829(16) 3_645
C19 C18 1.3829(16) 3_645
