#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119995.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_4119995
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                 97.164(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.539(6)
_cell_length_b                   8.3673(8)
_cell_length_c                   10.2441(9)
_cell_measurement_temperature    295(2)
_cell_volume                     2682.3(6)
_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      295(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27924
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.0748
_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)+(0.0801P)²+1.2470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                1772
_reflns_number_total             3847
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja4044517_si_002.cif
_cod_data_source_block           doubleBCO,295K
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4119995
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25567(7) 0.3564(3) -0.34081(18) 0.0803(7) Uani 1 1 d . . .
C1 C 0.29297(9) 0.2884(3) -0.3445(2) 0.0799(8) Uani 1 1 d . . .
H1 H 0.2997 0.2552 -0.4260 0.096 Uiso 1 1 calc R . .
C2 C 0.32289(7) 0.2625(3) -0.23665(19) 0.0644(6) Uani 1 1 d . . .
H2 H 0.3490 0.2147 -0.2459 0.077 Uiso 1 1 calc R . .
C3 C 0.27434(7) 0.3819(3) -0.1089(2) 0.0675(7) Uani 1 1 d . . .
H3 H 0.2665 0.4174 -0.0293 0.081 Uiso 1 1 calc R . .
C4 C 0.24736(8) 0.4011(3) -0.2242(2) 0.0821(8) Uani 1 1 d . . .
H4 H 0.2211 0.4497 -0.2188 0.098 Uiso 1 1 calc R . .
C5 C 0.31314(6) 0.3094(2) -0.11395(18) 0.0505(5) Uani 1 1 d . . .
C6 C 0.34258(7) 0.2862(3) 0.00346(19) 0.0581(6) Uani 1 1 d . . .
C7 C 0.36504(6) 0.2724(3) 0.10462(18) 0.0562(6) Uani 1 1 d . A .
C8 C 0.39201(6) 0.2620(2) 0.23187(17) 0.0458(5) Uani 1 1 d . . .
C9 C 0.43902(5) 0.2487(2) 0.45847(16) 0.0421(4) Uani 1 1 d . . .
C10 C 0.46559(6) 0.2424(2) 0.58617(17) 0.0459(5) Uani 1 1 d . . .
C11 C 0.48747(6) 0.2408(2) 0.69005(17) 0.0475(5) Uani 1 1 d . . .
C1A C 0.36406(7) 0.2497(4) 0.3449(2) 0.0648(7) Uani 0.88 1 d P A 1
H1A1 H 0.3445 0.3395 0.3406 0.078 Uiso 0.88 1 calc PR A 1
H1A2 H 0.3473 0.1523 0.3350 0.078 Uiso 0.88 1 calc PR A 1
C2A C 0.39180(7) 0.2490(4) 0.4782(2) 0.0613(7) Uani 0.88 1 d P A 1
H2A1 H 0.3854 0.1549 0.5276 0.074 Uiso 0.88 1 calc PR A 1
H2A2 H 0.3855 0.3427 0.5281 0.074 Uiso 0.88 1 calc PR A 1
C3A C 0.42093(10) 0.1174(4) 0.2400(2) 0.0735(9) Uani 0.88 1 d P A 1
H3A1 H 0.4401 0.1252 0.1731 0.088 Uiso 0.88 1 calc PR A 1
H3A2 H 0.4038 0.0217 0.2228 0.088 Uiso 0.88 1 calc PR A 1
C4A C 0.44720(11) 0.1044(4) 0.3759(3) 0.0740(9) Uani 0.88 1 d P A 1
H4A1 H 0.4394 0.0078 0.4194 0.089 Uiso 0.88 1 calc PR A 1
H4A2 H 0.4774 0.0983 0.3662 0.089 Uiso 0.88 1 calc PR A 1
C5A C 0.41893(11) 0.4134(3) 0.2567(3) 0.0702(8) Uani 0.88 1 d P A 1
H5A1 H 0.4003 0.5053 0.2582 0.084 Uiso 0.88 1 calc PR A 1
H5A2 H 0.4362 0.4281 0.1858 0.084 Uiso 0.88 1 calc PR A 1
C6A C 0.44789(10) 0.4019(3) 0.3874(2) 0.0698(8) Uani 0.88 1 d P A 1
H6A1 H 0.4776 0.4039 0.3715 0.084 Uiso 0.88 1 calc PR A 1
H6A2 H 0.4430 0.4931 0.4421 0.084 Uiso 0.88 1 calc PR A 1
C1B C 0.3796(9) 0.382(4) 0.310(2) 0.102(10) Uani 0.12 1 d P A 2
H1B1 H 0.3505 0.3630 0.3268 0.123 Uiso 0.12 1 calc PR A 2
H1B2 H 0.3805 0.4831 0.2643 0.123 Uiso 0.12 1 calc PR A 2
C2B C 0.4092(9) 0.389(3) 0.4407(19) 0.087(8) Uani 0.12 1 d P A 2
H2B1 H 0.4257 0.4868 0.4439 0.105 Uiso 0.12 1 calc PR A 2
H2B2 H 0.3919 0.3916 0.5127 0.105 Uiso 0.12 1 calc PR A 2
C3B C 0.3861(8) 0.096(3) 0.2893(17) 0.086(7) Uani 0.12 1 d P A 2
H3B1 H 0.3986 0.0145 0.2383 0.103 Uiso 0.12 1 calc PR A 2
H3B2 H 0.3560 0.0721 0.2893 0.103 Uiso 0.12 1 calc PR A 2
C4B C 0.4090(7) 0.101(3) 0.4301(18) 0.084(8) Uani 0.12 1 d P A 2
H4B1 H 0.4258 0.0040 0.4465 0.101 Uiso 0.12 1 calc PR A 2
H4B2 H 0.3877 0.1020 0.4909 0.101 Uiso 0.12 1 calc PR A 2
C5B C 0.4412(6) 0.276(4) 0.2058(16) 0.087(8) Uani 0.12 1 d P A 2
H5B1 H 0.4479 0.1960 0.1428 0.105 Uiso 0.12 1 calc PR A 2
H5B2 H 0.4470 0.3810 0.1720 0.105 Uiso 0.12 1 calc PR A 2
C6B C 0.4677(5) 0.248(3) 0.3397(14) 0.071(6) Uani 0.12 1 d P A 2
H6B1 H 0.4893 0.3310 0.3548 0.085 Uiso 0.12 1 calc PR A 2
H6B2 H 0.4823 0.1462 0.3383 0.085 Uiso 0.12 1 calc PR A 2
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 115.63(19) .
N1 C1 C2 124.9(2) .
N1 C1 H1 117.5 .
C2 C1 H1 117.5 .
C1 C2 C5 118.3(2) .
C1 C2 H2 120.8 .
C5 C2 H2 120.8 .
C4 C3 C5 118.6(2) .
C4 C3 H3 120.7 .
C5 C3 H3 120.7 .
N1 C4 C3 125.2(2) .
N1 C4 H4 117.4 .
C3 C4 H4 117.4 .
C3 C5 C2 117.29(17) .
C3 C5 C6 120.92(19) .
C2 C5 C6 121.8(2) .
C7 C6 C5 175.7(2) .
C6 C7 C8 177.4(2) .
C1B C8 C7 107.4(7) .
C1B C8 C3B 112.6(18) .
C7 C8 C3B 108.1(6) .
C1B C8 C3A 140.2(7) .
C7 C8 C3A 112.05(17) .
C3B C8 C3A 49.7(11) .
C1B C8 C5A 59.3(16) .
C7 C8 C5A 110.31(16) .
C3B C8 C5A 141.4(6) .
C3A C8 C5A 109.6(2) .
C1B C8 C1A 51.7(16) .
C7 C8 C1A 110.37(16) .
C3B C8 C1A 62.8(11) .
C3A C8 C1A 107.6(2) .
C5A C8 C1A 106.7(2) .
C1B C8 C5B 113.2(18) .
C7 C8 C5B 108.2(6) .
C3B C8 C5B 107.2(15) .
C3A C8 C5B 58.7(11) .
C5A C8 C5B 56.0(11) .
C1A C8 C5B 141.3(6) .
C10 C9 C2B 114.7(7) .
C10 C9 C4A 110.60(15) .
C2B C9 C4A 134.7(7) .
C10 C9 C6A 109.88(15) .
C2B C9 C6A 55.4(12) .
C4A C9 C6A 110.5(2) .
C10 C9 C2A 109.92(16) .
C2B C9 C2A 53.7(13) .
C4A C9 C2A 108.2(2) .
C6A C9 C2A 107.7(2) .
C10 C9 C4B 113.8(6) .
C2B C9 C4B 103.9(15) .
C4A C9 C4B 53.6(11) .
C6A C9 C4B 136.3(6) .
C2A C9 C4B 56.5(11) .
C10 C9 C6B 111.3(5) .
C2B C9 C6B 108.4(14) .
C4A C9 C6B 54.7(10) .
C6A C9 C6B 58.9(10) .
C2A C9 C6B 138.8(5) .
C4B C9 C6B 104.1(13) .
C11 C10 C9 178.5(2) .
C10 C11 C11 179.35(19) 2_656
C2A C1A C8 110.73(18) .
C2A C1A H1A1 109.5 .
C8 C1A H1A1 109.5 .
C2A C1A H1A2 109.5 .
C8 C1A H1A2 109.5 .
H1A1 C1A H1A2 108.1 .
C1A C2A C9 109.92(18) .
C1A C2A H2A1 109.7 .
C9 C2A H2A1 109.7 .
C1A C2A H2A2 109.7 .
C9 C2A H2A2 109.7 .
H2A1 C2A H2A2 108.2 .
C8 C3A C4A 111.16(18) .
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 109.91(18) .
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 110.68(18) .
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 110.34(18) .
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 .
C8 C1B C2B 110.7(15) .
C8 C1B H1B1 109.5 .
C2B C1B H1B1 109.5 .
C8 C1B H1B2 109.5 .
C2B C1B H1B2 109.5 .
H1B1 C1B H1B2 108.1 .
C9 C2B C1B 112.2(15) .
C9 C2B H2B1 109.2 .
C1B C2B H2B1 109.2 .
C9 C2B H2B2 109.2 .
C1B C2B H2B2 109.2 .
H2B1 C2B H2B2 107.9 .
C8 C3B C4B 105.7(14) .
C8 C3B H3B1 110.6 .
C4B C3B H3B1 110.6 .
C8 C3B H3B2 110.6 .
C4B C3B H3B2 110.6 .
H3B1 C3B H3B2 108.7 .
C3B C4B C9 113.6(14) .
C3B C4B H4B1 108.8 .
C9 C4B H4B1 108.8 .
C3B C4B H4B2 108.8 .
C9 C4B H4B2 108.8 .
H4B1 C4B H4B2 107.7 .
C6B C5B C8 105.7(12) .
C6B C5B H5B1 110.6 .
C8 C5B H5B1 110.6 .
C6B C5B H5B2 110.6 .
C8 C5B H5B2 110.6 .
H5B1 C5B H5B2 108.7 .
C5B C6B C9 112.4(12) .
C5B C6B H6B1 109.1 .
C9 C6B H6B1 109.1 .
C5B C6B H6B2 109.1 .
C9 C6B H6B2 109.1 .
H6B1 C6B H6B2 107.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.311(3) .
N1 C4 1.310(3) .
C1 C2 1.378(3) .
C1 H1 0.9300 .
C2 C5 1.388(3) .
C2 H2 0.9300 .
C3 C4 1.376(3) .
C3 C5 1.373(3) .
C3 H3 0.9300 .
C4 H4 0.9300 .
C5 C6 1.438(2) .
C6 C7 1.186(2) .
C7 C8 1.468(2) .
C8 C1B 1.37(2) .
C8 C3B 1.53(2) .
C8 C3A 1.511(3) .
C8 C5A 1.528(3) .
C8 C1A 1.543(3) .
C8 C5B 1.612(18) .
C9 C10 1.464(2) .
C9 C2B 1.501(19) .
C9 C4A 1.515(3) .
C9 C6A 1.517(3) .
C9 C2A 1.528(3) .
C9 C4B 1.565(19) .
C9 C6B 1.605(16) .
C10 C11 1.194(2) .
C11 C11 1.375(3) 2_656
C1A C2A 1.528(3) .
C1A H1A1 0.9700 .
C1A H1A2 0.9700 .
C2A H2A1 0.9700 .
C2A H2A2 0.9700 .
C3A C4A 1.532(3) .
C3A H3A1 0.9700 .
C3A H3A2 0.9700 .
C4A H4A1 0.9700 .
C4A H4A2 0.9700 .
C5A C6A 1.527(3) .
C5A H5A1 0.9700 .
C5A H5A2 0.9700 .
C6A H6A1 0.9700 .
C6A H6A2 0.9700 .
C1B C2B 1.54(2) .
C1B H1B1 0.9700 .
C1B H1B2 0.9700 .
C2B H2B1 0.9700 .
C2B H2B2 0.9700 .
C3B C4B 1.53(2) .
C3B H3B1 0.9700 .
C3B H3B2 0.9700 .
C4B H4B1 0.9700 .
C4B H4B2 0.9700 .
C5B C6B 1.53(2) .
C5B H5B1 0.9700 .
C5B H5B2 0.9700 .
C6B H6B1 0.9700 .
C6B H6B2 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 2.93 3.603(3) 130.3 7_554
C3 H3 N1 0.93 2.76 3.618(3) 154.6 6_566
