#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/93/2239388.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239388
loop_
_publ_author_name
'Zhang, Shuguang'
'Zhuang, Junpeng'
_publ_section_title
;
 r-1,t-3-Bis[4-(dimethylamino)phenyl]-c-2,t-4-bis(pyridin-4-yl)cyclobutane
;
_journal_coeditor_code           MW2110
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o311
_journal_paper_doi               10.1107/S1600536814002311
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C30 H32 N4'
_chemical_formula_moiety         'C30 H32 N4'
_chemical_formula_sum            'C30 H32 N4'
_chemical_formula_weight         448.60
_chemical_name_systematic
r-1,t-3-Bis[4-(dimethylamino)phenyl]-c-2,t-4-bis(pyridin-4-yl)cyclobutane
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.166(5)
_cell_length_b                   11.003(2)
_cell_length_c                   9.6330(19)
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.896
_cell_measurement_theta_min      1.759
_cell_volume                     2454.4(8)
_computing_cell_refinement       'CrystalClear (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14966
_diffrn_reflns_theta_full        27.850
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.258
_refine_ls_extinction_coef       0.0115(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0689P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2335
_reflns_number_total             2934
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mw2110sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2239388
_cod_database_fobs_code          2239388
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
N N1 -0.12781(4) 0.08386(9) 0.34546(11) 0.0261(3) Uani d 1
N N2 0.21597(4) 0.48468(8) 0.38134(10) 0.0201(3) Uani d 1
C C1 -0.14278(5) 0.08343(11) 0.47858(13) 0.0215(3) Uani d 1
H H1 -0.1758 0.0408 0.5017 0.026 Uiso calc 1
C C2 -0.11207(5) 0.14263(10) 0.58397(12) 0.0191(3) Uani d 1
H H2 -0.1241 0.1375 0.6750 0.023 Uiso calc 1
C C3 -0.06316(5) 0.20975(10) 0.55322(12) 0.0166(3) Uani d 1
C C4 -0.04739(5) 0.21074(11) 0.41486(12) 0.0233(3) Uani d 1
H H4 -0.0151 0.2541 0.3884 0.028 Uiso calc 1
C C5 -0.08012(6) 0.14681(12) 0.31670(13) 0.0289(3) Uani d 1
H H5 -0.0683 0.1477 0.2253 0.035 Uiso calc 1
C C6 -0.02904(5) 0.27871(10) 0.66140(12) 0.0170(3) Uani d 1
H H6 -0.0342 0.3661 0.6456 0.020 Uiso calc 1
C C7 0.03660(4) 0.25051(10) 0.68241(11) 0.0165(3) Uani d 1
H H7 0.0421 0.1627 0.6722 0.020 Uiso calc 1
C C8 0.08169(5) 0.31420(10) 0.60052(11) 0.0165(3) Uani d 1
C C9 0.12213(5) 0.24764(10) 0.52824(12) 0.0191(3) Uani d 1
H H9 0.1200 0.1633 0.5298 0.023 Uiso calc 1
C C10 0.16550(5) 0.30229(10) 0.45398(12) 0.0204(3) Uani d 1
H H10 0.1914 0.2541 0.4065 0.024 Uiso calc 1
C C11 0.17092(5) 0.42906(10) 0.44948(11) 0.0172(3) Uani d 1
C C12 0.12953(5) 0.49722(10) 0.52068(12) 0.0196(3) Uani d 1
H H12 0.1312 0.5816 0.5186 0.023 Uiso calc 1
C C13 0.08643(5) 0.44051(11) 0.59377(12) 0.0193(3) Uani d 1
H H13 0.0599 0.4881 0.6397 0.023 Uiso calc 1
C C14 0.24760(5) 0.41298(11) 0.28156(13) 0.0240(3) Uani d 1
H H14A 0.2213 0.3836 0.2103 0.036 Uiso calc 1
H H14B 0.2658 0.3453 0.3281 0.036 Uiso calc 1
H H14C 0.2766 0.4628 0.2405 0.036 Uiso calc 1
C C15 0.21211(5) 0.61429(10) 0.35107(13) 0.0230(3) Uani d 1
H H15A 0.2091 0.6588 0.4363 0.034 Uiso calc 1
H H15B 0.1786 0.6297 0.2927 0.034 Uiso calc 1
H H15C 0.2461 0.6398 0.3043 0.034 Uiso calc 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 C5 . . 116.00(11)
C11 N2 C14 . . 118.14(10)
C11 N2 C15 . . 118.84(9)
C14 N2 C15 . . 115.26(9)
N1 C1 C2 . . 123.96(11)
N1 C1 H1 . . 118.0
C2 C1 H1 . . 118.0
C1 C2 C3 . . 119.84(11)
C1 C2 H2 . . 120.1
C3 C2 H2 . . 120.1
C2 C3 C4 . . 116.48(11)
C2 C3 C6 . . 122.53(10)
C4 C3 C6 . . 120.99(10)
C5 C4 C3 . . 119.70(11)
C5 C4 H4 . . 120.2
C3 C4 H4 . . 120.2
N1 C5 C4 . . 124.00(11)
N1 C5 H5 . . 118.0
C4 C5 H5 . . 118.0
C3 C6 C7 . 2_556 120.12(9)
C3 C6 C7 . . 118.86(9)
C7 C6 C7 2_556 . 88.36(9)
C3 C6 H6 . . 109.3
C7 C6 H6 2_556 . 109.3
C7 C6 H6 . . 109.3
C8 C7 C6 . 2_556 121.09(10)
C8 C7 C6 . . 121.99(9)
C6 C7 C6 2_556 . 87.07(9)
C8 C7 H7 . . 108.2
C6 C7 H7 2_556 . 108.2
C6 C7 H7 . . 108.2
C9 C8 C13 . . 116.46(10)
C9 C8 C7 . . 120.41(10)
C13 C8 C7 . . 123.12(10)
C10 C9 C8 . . 122.55(11)
C10 C9 H9 . . 118.7
C8 C9 H9 . . 118.7
C9 C10 C11 . . 120.95(10)
C9 C10 H10 . . 119.5
C11 C10 H10 . . 119.5
N2 C11 C10 . . 121.45(10)
N2 C11 C12 . . 121.70(10)
C10 C11 C12 . . 116.83(10)
C13 C12 C11 . . 121.14(11)
C13 C12 H12 . . 119.4
C11 C12 H12 . . 119.4
C12 C13 C8 . . 122.04(10)
C12 C13 H13 . . 119.0
C8 C13 H13 . . 119.0
N2 C14 H14A . . 109.5
N2 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
N2 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
N2 C15 H15A . . 109.5
N2 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
N2 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.3381(15)
N1 C5 . 1.3396(16)
N2 C11 . 1.3908(14)
N2 C14 . 1.4576(15)
N2 C15 . 1.4579(14)
C1 C2 . 1.3853(17)
C1 H1 . 0.9300
C2 C3 . 1.3916(15)
C2 H2 . 0.9300
C3 C4 . 1.3923(16)
C3 C6 . 1.4961(16)
C4 C5 . 1.3863(17)
C4 H4 . 0.9300
C5 H5 . 0.9300
C6 C7 2_556 1.5512(15)
C6 C7 . 1.5593(15)
C6 H6 . 0.9800
C7 C8 . 1.5008(15)
C7 C6 2_556 1.5512(15)
C7 H7 . 0.9800
C8 C9 . 1.3918(15)
C8 C13 . 1.3958(16)
C9 C10 . 1.3874(15)
C9 H9 . 0.9300
C10 C11 . 1.4013(16)
C10 H10 . 0.9300
C11 C12 . 1.4109(16)
C12 C13 . 1.3867(16)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15B Cg1 5_566 0.96 2.82 3.679(2) 149
C12 H12 Cg2 5_566 0.96 3.12 4.104(2) 161
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 N1 C1 C2 . . -0.30(18)
N1 C1 C2 C3 . . 1.49(18)
C1 C2 C3 C4 . . -1.27(16)
C1 C2 C3 C6 . . 178.20(11)
C2 C3 C4 C5 . . 0.03(17)
C6 C3 C4 C5 . . -179.44(11)
C1 N1 C5 C4 . . -1.05(19)
C3 C4 C5 N1 . . 1.2(2)
C2 C3 C6 C7 . 2_556 16.79(16)
C4 C3 C6 C7 . 2_556 -163.77(10)
C2 C3 C6 C7 . . 123.18(12)
C4 C3 C6 C7 . . -57.38(15)
C3 C6 C7 C8 . . 88.20(13)
C7 C6 C7 C8 2_556 . -147.91(9)
C3 C6 C7 C6 . 2_556 -146.52(8)
C7 C6 C7 C6 2_556 2_556 -22.63(11)
C6 C7 C8 C9 2_556 . 125.21(12)
C6 C7 C8 C9 . . -126.96(12)
C6 C7 C8 C13 2_556 . -53.68(15)
C6 C7 C8 C13 . . 54.16(16)
C13 C8 C9 C10 . . 0.62(18)
C7 C8 C9 C10 . . -178.34(10)
C8 C9 C10 C11 . . 0.61(19)
C14 N2 C11 C10 . . 17.54(17)
C15 N2 C11 C10 . . 165.43(11)
C14 N2 C11 C12 . . -164.33(11)
C15 N2 C11 C12 . . -16.44(17)
C9 C10 C11 N2 . . 176.66(11)
C9 C10 C11 C12 . . -1.55(17)
N2 C11 C12 C13 . . -176.89(11)
C10 C11 C12 C13 . . 1.32(17)
C11 C12 C13 C8 . . -0.12(18)
C9 C8 C13 C12 . . -0.86(17)
C7 C8 C13 C12 . . 178.07(11)
