#------------------------------------------------------------------------------
#$Date: 2016-06-16 18:45:44 +0300 (Thu, 16 Jun 2016) $
#$Revision: 183549 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/34/1543453.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_1543453
loop_
_publ_author_name
'Zhu, Yangjie'
'Chen, Weiping'
'Wang, Tong'
'Wang, Haibo'
'Wang, Yue'
'Yan, Donghang'
_publ_section_title
;
 Highly Crystalline Films of Organic Small Molecules with Alkyl Chains
 Fabricated by Weak Epitaxy Growth.
;
_journal_issue                   18
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              4310
_journal_page_last               4318
_journal_paper_doi               10.1021/acs.jpcb.6b01579
_journal_volume                  120
_journal_year                    2016
_chemical_formula_sum            'C60 H58 Cl4 N4 O2'
_chemical_formula_weight         1008.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.2030(10)
_cell_angle_beta                 99.3240(10)
_cell_angle_gamma                107.0880(10)
_cell_formula_units_Z            1
_cell_length_a                   9.0158(6)
_cell_length_b                   12.2248(7)
_cell_length_c                   13.1669(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1265.20(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6814
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.283
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             530
_refine_diff_density_max         1.304
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1174P)²+1.0315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_ref         0.1993
_reflns_number_gt                3918
_reflns_number_total             4838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp6b01579_si_002.cif
_cod_data_source_block           1
_cod_database_code               1543453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.11170(10) 0.47353(8) 0.37202(7) 0.0452(3) Uani 1 1 d .
N1 N -0.3307(3) 0.8491(2) 0.41468(18) 0.0220(5) Uani 1 1 d .
O1 O -0.1487(3) 1.1101(2) 0.73350(18) 0.0483(7) Uani 1 1 d .
Cl2 Cl 0.02745(10) 0.60751(8) 0.21242(7) 0.0425(3) Uani 1 1 d .
C2 C -0.4167(3) 0.9221(2) 0.4557(2) 0.0212(5) Uani 1 1 d .
N2 N 0.2490(3) 0.8935(2) 0.6767(2) 0.0274(5) Uani 1 1 d .
C3 C -0.1874(3) 0.8584(2) 0.4820(2) 0.0230(6) Uani 1 1 d .
C4 C -0.3523(3) 1.0146(2) 0.5646(2) 0.0222(6) Uani 1 1 d .
C6 C -0.5659(3) 0.9095(2) 0.3934(2) 0.0216(5) Uani 1 1 d .
H6A H -0.6117 0.8485 0.3221 0.026 Uiso 1 1 calc R
C7 C 0.0309(3) 0.9531(2) 0.6574(2) 0.0234(6) Uani 1 1 d .
C9 C -0.3967(3) 0.7578(2) 0.2993(2) 0.0230(6) Uani 1 1 d .
H9A H -0.3082 0.7466 0.2696 0.028 Uiso 1 1 calc R
H9B H -0.4553 0.7893 0.2543 0.028 Uiso 1 1 calc R
C10 C 0.1044(3) 0.8723(3) 0.6055(2) 0.0252(6) Uani 1 1 d .
C11 C -0.1102(3) 0.7765(3) 0.4379(2) 0.0271(6) Uani 1 1 d .
H11A H -0.1585 0.7162 0.3663 0.032 Uiso 1 1 calc R
C12 C -0.1187(3) 0.9469(2) 0.5930(2) 0.0219(5) Uani 1 1 d .
C13 C 0.0334(3) 0.7837(3) 0.4978(2) 0.0274(6) Uani 1 1 d .
H13A H 0.0831 0.7298 0.4669 0.033 Uiso 1 1 calc R
C14 C -0.1996(3) 1.0304(3) 0.6387(2) 0.0252(6) Uani 1 1 d .
C15 C 0.1395(3) 1.0272(3) 0.7695(2) 0.0250(6) Uani 1 1 d .
C16 C -0.0229(4) 0.4480(3) 0.1619(3) 0.0335(7) Uani 1 1 d .
C17 C 0.2721(3) 0.9869(3) 0.7758(2) 0.0265(6) Uani 1 1 d .
C18 C 0.1418(3) 1.1218(3) 0.8650(2) 0.0307(6) Uani 1 1 d .
H18A H 0.0565 1.1498 0.8647 0.037 Uiso 1 1 calc R
C19 C 0.0169(3) 0.3895(3) 0.2302(3) 0.0325(7) Uani 1 1 d .
C20 C 0.3622(3) 0.8328(3) 0.6483(3) 0.0289(6) Uani 1 1 d .
H20A H 0.4708 0.8894 0.6923 0.035 Uiso 1 1 calc R
H20B H 0.3575 0.8157 0.5705 0.035 Uiso 1 1 calc R
C21 C 0.4018(4) 1.1319(3) 0.9614(3) 0.0384(8) Uani 1 1 d .
H21A H 0.4884 1.1688 1.0254 0.046 Uiso 1 1 calc R
C22 C 0.4039(4) 1.0395(3) 0.8718(3) 0.0344(7) Uani 1 1 d .
H22A H 0.4897 1.0119 0.8741 0.041 Uiso 1 1 calc R
C23 C -0.1022(4) 0.3793(3) 0.0501(3) 0.0417(8) Uani 1 1 d .
H23A H -0.1321 0.4179 0.0040 0.050 Uiso 1 1 calc R
C24 C -0.0188(4) 0.2630(3) 0.1875(3) 0.0430(8) Uani 1 1 d .
H24A H 0.0083 0.2239 0.2339 0.052 Uiso 1 1 calc R
C25 C -0.5092(3) 0.6333(3) 0.2909(2) 0.0288(6) Uani 1 1 d .
H25A H -0.6028 0.6431 0.3142 0.035 Uiso 1 1 calc R
H25B H -0.4537 0.6052 0.3411 0.035 Uiso 1 1 calc R
C26 C -0.0952(5) 0.1952(3) 0.0753(3) 0.0493(9) Uani 1 1 d .
H26A H -0.1183 0.1104 0.0459 0.059 Uiso 1 1 calc R
C27 C -0.5653(4) 0.5355(3) 0.1731(3) 0.0369(7) Uani 1 1 d .
H27A H -0.6111 0.5674 0.1220 0.044 Uiso 1 1 calc R
H27B H -0.6501 0.4627 0.1695 0.044 Uiso 1 1 calc R
C28 C 0.2713(4) 1.1725(3) 0.9590(3) 0.0407(8) Uani 1 1 d .
H28A H 0.2721 1.2347 1.0218 0.049 Uiso 1 1 calc R
C29 C -0.4296(4) 0.4975(3) 0.1349(3) 0.0471(9) Uani 1 1 d .
H29A H -0.4722 0.4363 0.0603 0.071 Uiso 1 1 calc R
H29B H -0.3857 0.4636 0.1837 0.071 Uiso 1 1 calc R
H29C H -0.3460 0.5687 0.1369 0.071 Uiso 1 1 calc R
C30 C -0.1368(4) 0.2528(3) 0.0073(3) 0.0482(9) Uani 1 1 d .
H30A H -0.1886 0.2067 -0.0680 0.058 Uiso 1 1 calc R
C31 C 0.3305(5) 0.7133(4) 0.6672(4) 0.0508(10) Uani 1 1 d .
H31A H 0.2183 0.6595 0.6305 0.061 Uiso 1 1 calc R
H31B H 0.3498 0.7308 0.7463 0.061 Uiso 1 1 calc R
C32 C 0.4415(6) 0.6469(4) 0.6209(5) 0.0702(13) Uani 1 1 d .
H32A H 0.4038 0.5629 0.6184 0.084 Uiso 1 1 calc R
H32B H 0.4371 0.6429 0.5457 0.084 Uiso 1 1 calc R
C33 C 0.6065(7) 0.7128(6) 0.6908(6) 0.100(2) Uani 1 1 d .
H33A H 0.6740 0.6707 0.6613 0.150 Uiso 1 1 calc R
H33B H 0.6108 0.7157 0.7650 0.150 Uiso 1 1 calc R
H33C H 0.6440 0.7955 0.6925 0.150 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 N1 C3 121.1(2) .
C2 N1 C9 118.6(2) .
C3 N1 C9 120.2(2) .
N1 C2 C6 122.8(2) .
N1 C2 C4 119.8(2) .
C6 C2 C4 117.4(2) .
C17 N2 C10 108.2(2) .
C17 N2 C20 126.3(2) .
C10 N2 C20 125.4(2) .
N1 C3 C11 118.7(2) .
N1 C3 C12 121.7(2) .
C11 C3 C12 119.6(2) .
C6 C4 C2 120.9(2) 2_476
C6 C4 C14 117.8(2) 2_476
C2 C4 C14 121.3(2) .
C4 C6 C2 121.7(2) 2_476
C10 C7 C12 117.9(2) .
C10 C7 C15 105.4(2) .
C12 C7 C15 136.6(2) .
N1 C9 C25 112.4(2) .
N2 C10 C13 127.0(2) .
N2 C10 C7 110.6(2) .
C13 C10 C7 122.4(2) .
C13 C11 C3 121.6(3) .
C3 C12 C7 118.9(2) .
C3 C12 C14 119.5(2) .
C7 C12 C14 121.5(2) .
C11 C13 C10 119.3(2) .
O1 C14 C12 124.0(2) .
O1 C14 C4 119.6(2) .
C12 C14 C4 116.4(2) .
C18 C15 C17 117.4(3) .
C18 C15 C7 136.5(3) .
C17 C15 C7 106.1(2) .
C19 C16 C23 119.7(3) .
C19 C16 Cl2 121.4(2) .
C23 C16 Cl2 118.9(3) .
N2 C17 C22 127.8(3) .
N2 C17 C15 109.7(2) .
C22 C17 C15 122.4(3) .
C28 C18 C15 119.7(3) .
C16 C19 C24 120.5(3) .
C16 C19 Cl1 120.5(2) .
C24 C19 Cl1 119.0(3) .
N2 C20 C31 114.2(2) .
C22 C21 C28 121.2(3) .
C21 C22 C17 117.9(3) .
C16 C23 C30 119.7(3) .
C26 C24 C19 119.5(3) .
C9 C25 C27 112.3(2) .
C30 C26 C24 120.1(3) .
C25 C27 C29 113.4(3) .
C18 C28 C21 121.2(3) .
C26 C30 C23 120.4(3) .
C20 C31 C32 110.7(3) .
C33 C32 C31 110.3(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C19 1.744(3) .
N1 C2 1.390(3) .
N1 C3 1.395(3) .
N1 C9 1.471(3) .
O1 C14 1.229(3) .
Cl2 C16 1.738(3) .
C2 C6 1.395(4) .
C2 C4 1.416(4) .
N2 C17 1.374(4) .
N2 C10 1.378(3) .
N2 C20 1.459(3) .
C3 C11 1.415(4) .
C3 C12 1.419(4) .
C4 C6 1.388(4) 2_476
C4 C14 1.475(4) .
C6 C4 1.388(4) 2_476
C7 C10 1.411(4) .
C7 C12 1.440(4) .
C7 C15 1.460(4) .
C9 C25 1.519(4) .
C10 C13 1.390(4) .
C11 C13 1.366(4) .
C12 C14 1.460(4) .
C15 C18 1.410(4) .
C15 C17 1.421(4) .
C16 C19 1.377(5) .
C16 C23 1.384(4) .
C17 C22 1.407(4) .
C18 C28 1.380(4) .
C19 C24 1.384(5) .
C20 C31 1.510(4) .
C21 C22 1.362(5) .
C21 C28 1.405(5) .
C23 C30 1.387(5) .
C24 C26 1.383(5) .
C25 C27 1.524(4) .
C26 C30 1.370(6) .
C27 C29 1.534(4) .
C31 C32 1.548(6) .
C32 C33 1.448(8) .
