#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119996.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_4119996
loop_
_publ_author_name
'Cyprien Lemouchi'
'Konstantinos Iliopoulos'
'Leokadiya Zorina'
'Sergey Simonov'
'Pawel Wzietek'
'Thomas Cauchy'
'Antonio Rodríguez-Fortea'
'Enric Canadell'
'Jiří Kaleta'
'Josef Michl'
'Denis Gindre'
'Michael Chrysos'
'Patrick Batail'
_publ_contact_author_address
;
Laboratoire MOLTECH-Anjou, CNRS, Université d'Angers,
UMR 6200, 49045 Angers, France
;
_publ_contact_author_email       patrick.batail@univ-angers.fr
_publ_contact_author_name        'Dr. Patrick Batail'
_publ_section_title
;
 Crystalline Arrays of Pairs of Molecular Rotors: Correlated Motion,
 Rotational Barriers, and Space-Inversion Symmetry Breaking Due to
 Conformational Mutations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9366
_journal_page_last               9376
_journal_paper_doi               10.1021/ja4044517
_journal_volume                  135
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C34 H32 N2'
_chemical_formula_sum            'C34 H32 N2'
_chemical_formula_weight         468.62
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 96.300(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.3333(16)
_cell_length_b                   8.3151(5)
_cell_length_c                   10.2204(9)
_cell_measurement_temperature    200(1)
_cell_volume                     2646.7(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       'combined 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  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20793
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0697
_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)+(0.0805P)²+4.2370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.2001
_reflns_number_gt                1844
_reflns_number_total             3152
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja4044517_si_003.cif
_cod_data_source_block           doubleBCO,200K
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4119996
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags
N1 N 0.25513(7) 0.3571(3) -0.3401(2) 0.0475(6) Uani 1 1 d .
C1 C 0.29308(9) 0.2891(4) -0.3456(2) 0.0491(7) Uani 1 1 d .
H1 H 0.3001 0.2562 -0.4275 0.059 Uiso 1 1 calc R
C2 C 0.32303(8) 0.2637(3) -0.2374(2) 0.0395(6) Uani 1 1 d .
H2 H 0.3493 0.2160 -0.2473 0.047 Uiso 1 1 calc R
C3 C 0.27357(8) 0.3832(3) -0.1069(2) 0.0418(6) Uani 1 1 d .
H3 H 0.2656 0.4185 -0.0267 0.050 Uiso 1 1 calc R
C4 C 0.24626(9) 0.4019(4) -0.2217(3) 0.0500(7) Uani 1 1 d .
H4 H 0.2197 0.4493 -0.2153 0.060 Uiso 1 1 calc R
C5 C 0.31306(7) 0.3108(3) -0.1138(2) 0.0298(5) Uani 1 1 d .
C6 C 0.34249(8) 0.2884(3) 0.0031(2) 0.0364(6) Uani 1 1 d .
C7 C 0.36509(7) 0.2740(3) 0.1044(2) 0.0344(6) Uani 1 1 d .
C8 C 0.39197(7) 0.2632(3) 0.23141(19) 0.0277(5) Uani 1 1 d .
C9 C 0.43904(6) 0.2488(3) 0.45836(19) 0.0258(5) Uani 1 1 d .
C10 C 0.46554(7) 0.2425(3) 0.5858(2) 0.0284(5) Uani 1 1 d .
C11 C 0.48741(7) 0.2404(3) 0.6902(2) 0.0284(5) Uani 1 1 d .
C1A C 0.36365(7) 0.2491(4) 0.3451(2) 0.0441(7) Uani 1 1 d .
H1A1 H 0.3474 0.1496 0.3363 0.053 Uiso 1 1 calc R
H1A2 H 0.3434 0.3377 0.3406 0.053 Uiso 1 1 calc R
C2A C 0.39122(7) 0.2518(3) 0.4784(2) 0.0404(6) Uani 1 1 d .
H2A1 H 0.3849 0.3481 0.5264 0.048 Uiso 1 1 calc R
H2A2 H 0.3844 0.1592 0.5300 0.048 Uiso 1 1 calc R
C3A C 0.42156(9) 0.1174(4) 0.2378(3) 0.0533(8) Uani 1 1 d .
H3A1 H 0.4412 0.1273 0.1711 0.064 Uiso 1 1 calc R
H3A2 H 0.4046 0.0209 0.2193 0.064 Uiso 1 1 calc R
C4A C 0.44743(9) 0.1024(3) 0.3741(2) 0.0505(8) Uani 1 1 d .
H4A1 H 0.4391 0.0051 0.4171 0.061 Uiso 1 1 calc R
H4A2 H 0.4778 0.0953 0.3643 0.061 Uiso 1 1 calc R
C5A C 0.41943(9) 0.4158(3) 0.2554(3) 0.0507(8) Uani 1 1 d .
H5A1 H 0.4008 0.5086 0.2591 0.061 Uiso 1 1 calc R
H5A2 H 0.4366 0.4312 0.1830 0.061 Uiso 1 1 calc R
C6A C 0.44901(9) 0.4024(3) 0.3848(2) 0.0464(7) Uani 1 1 d .
H6A1 H 0.4787 0.4006 0.3662 0.056 Uiso 1 1 calc R
H6A2 H 0.4450 0.4953 0.4395 0.056 Uiso 1 1 calc R
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_3
C1 N1 C4 116.0(2) .
N1 C1 C2 124.4(2) .
N1 C1 H1 117.8 .
C2 C1 H1 117.8 .
C5 C2 C1 118.8(2) .
C5 C2 H2 120.6 .
C1 C2 H2 120.6 .
C5 C3 C4 118.6(2) .
C5 C3 H3 120.7 .
C4 C3 H3 120.7 .
N1 C4 C3 124.9(3) .
N1 C4 H4 117.6 .
C3 C4 H4 117.6 .
C3 C5 C2 117.4(2) .
C3 C5 C6 120.5(2) .
C2 C5 C6 122.1(2) .
C7 C6 C5 176.0(3) .
C6 C7 C8 177.3(3) .
C7 C8 C3A 111.94(19) .
C7 C8 C5A 110.28(19) .
C3A C8 C5A 108.8(2) .
C7 C8 C1A 110.40(18) .
C3A C8 C1A 107.8(2) .
C5A C8 C1A 107.5(2) .
C10 C9 C4A 110.83(18) .
C10 C9 C6A 109.88(18) .
C4A C9 C6A 109.3(2) .
C10 C9 C2A 110.35(17) .
C4A C9 C2A 108.6(2) .
C6A C9 C2A 107.87(19) .
C11 C10 C9 178.7(2) .
C10 C11 C11 179.16(19) 2_656
C8 C1A C2A 110.74(18) .
C8 C1A H1A1 109.5 .
C2A C1A H1A1 109.5 .
C8 C1A H1A2 109.5 .
C2A C1A H1A2 109.5 .
H1A1 C1A H1A2 108.1 .
C9 C2A C1A 110.17(18) .
C9 C2A H2A1 109.6 .
C1A C2A H2A1 109.6 .
C9 C2A H2A2 109.6 .
C1A C2A H2A2 109.6 .
H2A1 C2A H2A2 108.1 .
C8 C3A C4A 111.2(2) .
C8 C3A H3A1 109.4 .
C4A C3A H3A1 109.4 .
C8 C3A H3A2 109.4 .
C4A C3A H3A2 109.4 .
H3A1 C3A H3A2 108.0 .
C9 C4A C3A 109.8(2) .
C9 C4A H4A1 109.7 .
C3A C4A H4A1 109.7 .
C9 C4A H4A2 109.7 .
C3A C4A H4A2 109.7 .
H4A1 C4A H4A2 108.2 .
C8 C5A C6A 110.6(2) .
C8 C5A H5A1 109.5 .
C6A C5A H5A1 109.5 .
C8 C5A H5A2 109.5 .
C6A C5A H5A2 109.5 .
H5A1 C5A H5A2 108.1 .
C9 C6A C5A 110.33(19) .
C9 C6A H6A1 109.6 .
C5A C6A H6A1 109.6 .
C9 C6A H6A2 109.6 .
C5A C6A H6A2 109.6 .
H6A1 C6A H6A2 108.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.323(4) .
N1 C4 1.324(3) .
C1 C2 1.386(3) .
C1 H1 0.9300 .
C2 C5 1.391(3) .
C2 H2 0.9300 .
C3 C5 1.385(3) .
C3 C4 1.384(3) .
C3 H3 0.9300 .
C4 H4 0.9300 .
C5 C6 1.439(3) .
C6 C7 1.194(3) .
C7 C8 1.470(3) .
C8 C3A 1.523(3) .
C8 C5A 1.538(3) .
C8 C1A 1.542(3) .
C9 C10 1.467(3) .
C9 C4A 1.531(3) .
C9 C6A 1.532(3) .
C9 C2A 1.535(3) .
C10 C11 1.204(3) .
C11 C11 1.380(4) 2_656
C1A C2A 1.531(3) .
C1A H1A1 0.9700 .
C1A H1A2 0.9700 .
C2A H2A1 0.9700 .
C2A H2A2 0.9700 .
C3A C4A 1.538(3) .
C3A H3A1 0.9700 .
C3A H3A2 0.9700 .
C4A H4A1 0.9700 .
C4A H4A2 0.9700 .
C5A C6A 1.533(3) .
C5A H5A1 0.9700 .
C5A H5A2 0.9700 .
C6A H6A1 0.9700 .
C6A H6A2 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 N1 0.93 2.94 3.607(3) 130.2 7_554
C3 H3 N1 0.93 2.71 3.574(3) 154.3 6_566
