#------------------------------------------------------------------------------
#$Date: 2016-04-05 18:34:36 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181621 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/45/7224555.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_7224555
loop_
_publ_author_name
'Yu, Hai-Bin'
'Li, Hai-Tao'
'Zhang, Peng'
'Famulari, Antonino'
'Guo, Fang'
'Bargigia, Ilaria'
'Martí-Rujas, Javier'
_publ_section_title
;
 Exploiting polymorphism in second sphere coordination: thermal
 transformation, NLO properties and selective mechanochemical synthesis
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2408
_journal_paper_doi               10.1039/C6CE00366D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C34 H38 N2'
_chemical_formula_weight         474.66
_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
_audit_update_record
;
2016-02-10 deposited with the CCDC.
2016-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.739(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.33(3)
_cell_length_b                   11.523(17)
_cell_length_c                   14.65(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2802(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8177
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.065
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0539
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0805P)²+0.2354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                1893
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00366d2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7224553--7224555.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7224555
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 -0.07600(6) 0.47642(10) -0.32313(9) 0.0512(3) Uani 1 1 d .
C1 C -0.04583(8) 0.58646(12) -0.27496(11) 0.0501(4) Uani 1 1 d .
H1 H -0.0721 0.5960 -0.2245 0.060 Uiso 1 1 calc R
C2 C -0.04497(10) 0.45240(13) -0.40499(12) 0.0590(4) Uani 1 1 d .
H2A H 0.0125 0.4680 -0.3868 0.071 Uiso 1 1 calc R
H2B H -0.0708 0.5044 -0.4569 0.071 Uiso 1 1 calc R
C3 C -0.20113(8) 0.47216(14) -0.27147(12) 0.0572(4) Uani 1 1 d .
C4 C -0.05947(9) 0.32955(14) -0.43901(12) 0.0577(4) Uani 1 1 d .
C5 C -0.16449(8) 0.47023(15) -0.35304(12) 0.0628(4) Uani 1 1 d .
H5A H -0.1810 0.3995 -0.3893 0.075 Uiso 1 1 calc R
H5B H -0.1856 0.5352 -0.3949 0.075 Uiso 1 1 calc R
C6 C -0.06618(10) 0.69585(13) -0.33754(13) 0.0669(5) Uani 1 1 d .
H6A H -0.0371 0.6938 -0.3851 0.080 Uiso 1 1 calc R
H6B H -0.1234 0.6966 -0.3706 0.080 Uiso 1 1 calc R
C7 C -0.02036(11) 0.23947(16) -0.38200(14) 0.0735(5) Uani 1 1 d .
H7A H 0.0148 0.2555 -0.3222 0.088 Uiso 1 1 calc R
C8 C -0.18371(10) 0.38750(15) -0.20293(14) 0.0725(5) Uani 1 1 d .
H8A H -0.1471 0.3295 -0.2055 0.087 Uiso 1 1 calc R
C9 C -0.04405(11) 0.80596(14) -0.27838(16) 0.0833(6) Uani 1 1 d .
H9A H -0.0551 0.8730 -0.3202 0.100 Uiso 1 1 calc R
H9B H -0.0770 0.8120 -0.2352 0.100 Uiso 1 1 calc R
C10 C -0.25601(10) 0.55670(16) -0.26493(15) 0.0785(6) Uani 1 1 d .
H10A H -0.2686 0.6156 -0.3102 0.094 Uiso 1 1 calc R
C11 C -0.11140(11) 0.30310(18) -0.52721(14) 0.0798(6) Uani 1 1 d .
H11A H -0.1379 0.3626 -0.5668 0.096 Uiso 1 1 calc R
C12 C -0.21992(13) 0.3869(2) -0.12944(16) 0.0902(6) Uani 1 1 d .
H12A H -0.2074 0.3290 -0.0832 0.108 Uiso 1 1 calc R
C13 C -0.27391(12) 0.4717(2) -0.12573(18) 0.0976(8) Uani 1 1 d .
H13A H -0.2981 0.4717 -0.0767 0.117 Uiso 1 1 calc R
C14 C -0.08525(19) 0.1019(2) -0.5011(3) 0.1162(10) Uani 1 1 d .
H14A H -0.0937 0.0256 -0.5221 0.139 Uiso 1 1 calc R
C15 C -0.29239(13) 0.5556(2) -0.19303(19) 0.0996(7) Uani 1 1 d .
H15A H -0.3298 0.6126 -0.1907 0.119 Uiso 1 1 calc R
C16 C -0.12447(15) 0.1897(3) -0.5574(2) 0.1086(9) Uani 1 1 d .
H16A H -0.1603 0.1731 -0.6166 0.130 Uiso 1 1 calc R
C17 C -0.03294(15) 0.12588(18) -0.4128(2) 0.1018(8) Uani 1 1 d .
H17A H -0.0062 0.0658 -0.3741 0.122 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_1
_geom_angle_site_symmetry_3
C1 N1 C2 112.90(12) . .
C1 N1 C5 112.37(11) . .
C2 N1 C5 109.99(14) . .
N1 C1 C6 115.54(16) . .
N1 C1 C1 113.67(8) . 2_554
C6 C1 C1 108.05(10) . 2_554
N1 C1 H1 106.3 . .
C6 C1 H1 106.3 . .
C1 C1 H1 106.3 2_554 .
N1 C2 C4 112.48(12) . .
N1 C2 H2A 109.1 . .
C4 C2 H2A 109.1 . .
N1 C2 H2B 109.1 . .
C4 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
C8 C3 C10 117.48(18) . .
C8 C3 C5 121.11(16) . .
C10 C3 C5 121.36(18) . .
C11 C4 C7 118.33(18) . .
C11 C4 C2 121.48(16) . .
C7 C4 C2 120.19(17) . .
N1 C5 C3 113.88(15) . .
N1 C5 H5A 108.8 . .
C3 C5 H5A 108.8 . .
N1 C5 H5B 108.8 . .
C3 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
C9 C6 C1 111.51(18) . .
C9 C6 H6A 109.3 . .
C1 C6 H6A 109.3 . .
C9 C6 H6B 109.3 . .
C1 C6 H6B 109.3 . .
H6A C6 H6B 108.0 . .
C17 C7 C4 120.7(2) . .
C17 C7 H7A 119.6 . .
C4 C7 H7A 119.6 . .
C3 C8 C12 121.1(2) . .
C3 C8 H8A 119.4 . .
C12 C8 H8A 119.4 . .
C9 C9 C6 111.20(12) 2_554 .
C9 C9 H9A 109.4 2_554 .
C6 C9 H9A 109.4 . .
C9 C9 H9B 109.4 2_554 .
C6 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
C15 C10 C3 121.5(2) . .
C15 C10 H10A 119.3 . .
C3 C10 H10A 119.3 . .
C4 C11 C16 120.9(2) . .
C4 C11 H11A 119.6 . .
C16 C11 H11A 119.6 . .
C13 C12 C8 119.6(2) . .
C13 C12 H12A 120.2 . .
C8 C12 H12A 120.2 . .
C15 C13 C12 120.3(2) . .
C15 C13 H13A 119.9 . .
C12 C13 H13A 119.9 . .
C16 C14 C17 120.1(2) . .
C16 C14 H14A 120.0 . .
C17 C14 H14A 120.0 . .
C13 C15 C10 120.1(2) . .
C13 C15 H15A 120.0 . .
C10 C15 H15A 120.0 . .
C14 C16 C11 120.3(2) . .
C14 C16 H16A 119.9 . .
C11 C16 H16A 119.9 . .
C14 C17 C7 119.7(2) . .
C14 C17 H17A 120.1 . .
C7 C17 H17A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.472(2) .
N1 C2 1.475(2) .
N1 C5 1.470(3) .
C1 C6 1.539(3) .
C1 C1 1.546(4) 2_554
C1 H1 0.9800 .
C2 C4 1.498(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C8 1.370(3) .
C3 C10 1.384(3) .
C3 C5 1.506(3) .
C4 C11 1.379(3) .
C4 C7 1.381(3) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C9 1.522(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C17 1.381(3) .
C7 H7A 0.9300 .
C8 C12 1.394(3) .
C8 H8A 0.9300 .
C9 C9 1.514(4) 2_554
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C15 1.375(3) .
C10 H10A 0.9300 .
C11 C16 1.378(4) .
C11 H11A 0.9300 .
C12 C13 1.365(3) .
C12 H12A 0.9300 .
C13 C15 1.352(3) .
C13 H13A 0.9300 .
C14 C16 1.357(4) .
C14 C17 1.377(4) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
C16 H16A 0.9300 .
C17 H17A 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C1 C6 59.33(18) . .
C5 N1 C1 C6 -65.77(16) . .
C2 N1 C1 C1 -66.4(2) . 2_554
C5 N1 C1 C1 168.46(15) . 2_554
C1 N1 C2 C4 166.40(12) . .
C5 N1 C2 C4 -67.21(16) . .
N1 C2 C4 C11 113.3(2) . .
N1 C2 C4 C7 -67.0(2) . .
C1 N1 C5 C3 -63.72(18) . .
C2 N1 C5 C3 169.59(14) . .
C8 C3 C5 N1 -60.6(2) . .
C10 C3 C5 N1 121.94(17) . .
N1 C1 C6 C9 171.17(12) . .
C1 C1 C6 C9 -60.24(19) 2_554 .
C11 C4 C7 C17 0.1(2) . .
C2 C4 C7 C17 -179.67(15) . .
C10 C3 C8 C12 -0.1(2) . .
C5 C3 C8 C12 -177.57(15) . .
C1 C6 C9 C9 56.3(2) . 2_554
C8 C3 C10 C15 -0.6(3) . .
C5 C3 C10 C15 176.91(16) . .
C7 C4 C11 C16 0.5(3) . .
C2 C4 C11 C16 -179.68(16) . .
C3 C8 C12 C13 0.2(3) . .
C8 C12 C13 C15 0.2(3) . .
C12 C13 C15 C10 -0.9(3) . .
C3 C10 C15 C13 1.1(3) . .
C17 C14 C16 C11 0.9(4) . .
C4 C11 C16 C14 -1.0(3) . .
C16 C14 C17 C7 -0.2(3) . .
C4 C7 C17 C14 -0.3(3) . .
