#------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/58/4505862.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_4505862
loop_
_publ_author_name
'Wu, Yuechao'
'Yin, Zongyou'
'Xiao, Jinchong'
'Liu, Yi'
'Wei, Fengxia'
'Tan, Ke Jie'
'Kloc, Christian'
'Huang, Ling'
'Yan, Qingyu'
'Hu, Fangzhong'
'Zhang, Hua'
'Zhang, Qichun'
_publ_section_title
;
 Crystal structure and phototransistor behavior of N-substituted
 heptacence.
;
_journal_issue                   4
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              1883
_journal_page_last               1886
_journal_paper_doi               10.1021/am3003389
_journal_volume                  4
_journal_year                    2012
_chemical_formula_sum            'C38 H18 N4'
_chemical_formula_weight         530.56
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.407(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.2945(12)
_cell_length_b                   3.8517(2)
_cell_length_c                   25.4884(15)
_cell_measurement_temperature    296(2)
_cell_volume                     2353.0(2)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPERP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'APEX II CCD detector'
_diffrn_measurement_method       'phi and omega 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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14986
_diffrn_reflns_theta_full        24.23
_diffrn_reflns_theta_max         24.23
_diffrn_reflns_theta_min         1.07
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0444
_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)+(0.0536P)²+0.3730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                2125
_reflns_number_total             3800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am3003389_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constra' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4505862
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C38 C 0.55672(9) 0.4145(6) 0.13784(10) 0.0304(6) Uani 1 1 d .
C37 C 0.53633(9) 0.4156(6) 0.04670(10) 0.0300(6) Uani 1 1 d .
C36 C 0.57810(10) 0.4156(7) 0.23621(10) 0.0356(7) Uani 1 1 d .
C35 C 0.59363(9) 0.3260(6) 0.18693(10) 0.0326(6) Uani 1 1 d .
C34 C 0.48476(9) 0.5863(6) 0.04901(9) 0.0296(6) Uani 1 1 d .
C33 C 0.55055(8) 0.3304(6) -0.00224(9) 0.0328(6) Uani 1 1 d .
H33A H 0.5840 0.2166 -0.0037 0.039 Uiso 1 1 calc R
H27A H 0.6204 0.3645 0.3652 0.039 Uiso 1 1 d R
H26A H 0.5405 0.6481 0.3684 0.039 Uiso 1 1 d R
H25A H 0.6541 0.1002 0.1536 0.039 Uiso 1 1 d R
H24A H 0.4157 0.9070 0.1641 0.039 Uiso 1 1 d R
H23A H 0.4518 0.9076 0.3226 0.039 Uiso 1 1 d R
H22A H 0.6880 0.1028 0.3121 0.039 Uiso 1 1 d R
H21A H 0.3922 1.0411 0.2462 0.039 Uiso 1 1 d R
H20A H 0.7131 -0.0329 0.2317 0.039 Uiso 1 1 d R
H11A H 0.8207 1.3303 0.0831 0.039 Uiso 1 1 d R
H10A H 1.0185 1.3334 -0.0833 0.039 Uiso 1 1 d R
H9A H 0.7105 0.5934 -0.1949 0.039 Uiso 1 1 d R
H8A H 0.6682 0.9225 0.0478 0.039 Uiso 1 1 d R
H7A H 0.8661 0.9600 -0.1598 0.039 Uiso 1 1 d R
H5A H 0.6487 0.5837 -0.1260 0.039 Uiso 1 1 d R
H4A H 0.6342 0.6949 -0.0430 0.039 Uiso 1 1 d R
H2A H 0.7363 1.1848 0.1075 0.039 Uiso 1 1 d R
H1A H 0.7950 0.7147 -0.2198 0.039 Uiso 1 1 d R
C32 C 0.48947(9) 0.6794(6) 0.19159(10) 0.0327(6) Uani 1 1 d .
C31 C 0.51180(11) 0.6797(7) 0.28831(10) 0.0398(7) Uani 1 1 d .
C30 C 0.50444(9) 0.5895(6) 0.14001(10) 0.0308(6) Uani 1 1 d .
C29 C 0.52630(10) 0.5908(6) 0.23847(9) 0.0335(6) Uani 1 1 d .
C28 C 0.61406(11) 0.3298(7) 0.28410(10) 0.0393(7) Uani 1 1 d .
C27 C 0.59731(12) 0.4225(8) 0.33357(11) 0.0495(8) Uani 1 1 d .
C26 C 0.54956(13) 0.5891(8) 0.33548(11) 0.0498(8) Uani 1 1 d .
C25 C 0.64385(10) 0.1594(7) 0.18619(10) 0.0413(7) Uani 1 1 d .
C24 C 0.43989(10) 0.8483(7) 0.19517(10) 0.0384(7) Uani 1 1 d .
C23 C 0.46142(12) 0.8490(7) 0.28989(11) 0.0480(8) Uani 1 1 d .
C22 C 0.66422(11) 0.1608(7) 0.28094(11) 0.0478(8) Uani 1 1 d .
C21 C 0.42595(11) 0.9305(7) 0.24438(11) 0.0462(7) Uani 1 1 d .
C20 C 0.67920(10) 0.0782(7) 0.23300(12) 0.0464(7) Uani 1 1 d .
C19 C 0.76274(9) 0.9910(6) -0.02906(10) 0.0330(6) Uani 1 1 d .
C18 C 0.80435(9) 1.1495(6) 0.00829(10) 0.0334(6) Uani 1 1 d .
C17 C 0.85830(9) 1.2323(6) -0.00694(10) 0.0295(6) Uani 1 1 d .
C16 C 0.82416(9) 0.9877(6) -0.09799(10) 0.0329(6) Uani 1 1 d .
C15 C 0.77226(9) 0.9147(6) -0.08185(10) 0.0345(6) Uani 1 1 d .
C14 C 0.86888(9) 1.1421(6) -0.05958(9) 0.0297(6) Uani 1 1 d .
C13 C 0.95836(9) 1.3437(6) -0.03728(9) 0.0290(6) Uani 1 1 d .
C12 C 0.94725(9) 1.4443(6) 0.01388(9) 0.0293(6) Uani 1 1 d .
C11 C 0.79345(9) 1.2223(7) 0.05870(11) 0.0403(7) Uani 1 1 d .
C10 C 1.01102(9) 1.4006(6) -0.05001(9) 0.0318(6) Uani 1 1 d .
C9 C 0.73885(11) 0.6921(7) -0.17033(12) 0.0487(8) Uani 1 1 d .
C8 C 0.70213(10) 0.9809(8) 0.03762(12) 0.0486(8) Uani 1 1 d .
C7 C 0.83189(10) 0.9119(7) -0.14920(11) 0.0425(7) Uani 1 1 d .
C6 C 0.72923(10) 0.7630(7) -0.11905(11) 0.0405(7) Uani 1 1 d .
C5 C 0.67723(10) 0.6846(7) -0.10187(13) 0.0504(8) Uani 1 1 d .
C4 C 0.66852(10) 0.7514(8) -0.05257(13) 0.0510(8) Uani 1 1 d .
C3 C 0.71067(10) 0.9076(7) -0.01410(11) 0.0409(7) Uani 1 1 d .
C2 C 0.74278(10) 1.1364(8) 0.07325(11) 0.0489(8) Uani 1 1 d .
C1 C 0.78925(12) 0.7649(8) -0.18522(11) 0.0501(8) Uani 1 1 d .
N4 N 0.57189(7) 0.3300(5) 0.09222(8) 0.0340(5) Uani 1 1 d .
N3 N 0.46956(7) 0.6726(5) 0.09666(8) 0.0331(5) Uani 1 1 d .
N2 N 0.91772(7) 1.1953(5) -0.07394(8) 0.0328(5) Uani 1 1 d .
N1 N 0.89630(7) 1.3838(5) 0.02831(8) 0.0328(5) Uani 1 1 d .
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'
N N 0.0061 0.0033 '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'
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
N4 C38 C30 121.5(2) . .
N4 C38 C35 118.6(2) . .
C30 C38 C35 119.8(2) . .
N4 C37 C33 119.3(2) . .
N4 C37 C34 120.9(2) . .
C33 C37 C34 119.8(2) . .
C35 C36 C28 119.5(2) . .
C35 C36 C29 120.9(2) . .
C28 C36 C29 119.7(2) . .
C25 C35 C36 119.4(2) . .
C25 C35 C38 121.2(2) . .
C36 C35 C38 119.4(2) . .
N3 C34 C33 119.2(2) . 3_665
N3 C34 C37 121.1(2) . .
C33 C34 C37 119.7(2) 3_665 .
C37 C33 C34 120.5(2) . 3_665
C37 C33 H33A 119.7 . .
C34 C33 H33A 119.7 3_665 .
C24 C32 C29 119.7(2) . .
C24 C32 C30 121.2(2) . .
C29 C32 C30 119.2(2) . .
C23 C31 C29 119.2(2) . .
C23 C31 C26 122.4(3) . .
C29 C31 C26 118.4(3) . .
N3 C30 C38 122.0(2) . .
N3 C30 C32 118.5(2) . .
C38 C30 C32 119.6(2) . .
C32 C29 C31 119.0(2) . .
C32 C29 C36 121.1(2) . .
C31 C29 C36 119.9(2) . .
C22 C28 C36 118.7(2) . .
C22 C28 C27 122.9(3) . .
C36 C28 C27 118.4(3) . .
C26 C27 C28 121.7(3) . .
C26 C27 H27A 119.3 . .
C28 C27 H27A 118.9 . .
C27 C26 C31 121.9(3) . .
C27 C26 H26A 119.1 . .
C31 C26 H26A 119.0 . .
C35 C25 C20 121.1(3) . .
C35 C25 H25A 119.3 . .
C20 C25 H25A 119.5 . .
C32 C24 C21 120.7(2) . .
C32 C24 H24A 119.4 . .
C21 C24 H24A 119.9 . .
C21 C23 C31 121.3(2) . .
C21 C23 H23A 119.4 . .
C31 C23 H23A 119.4 . .
C20 C22 C28 121.5(2) . .
C20 C22 H22A 119.3 . .
C28 C22 H22A 119.3 . .
C23 C21 C24 120.2(2) . .
C23 C21 H21A 120.1 . .
C24 C21 H21A 119.7 . .
C22 C20 C25 119.9(3) . .
C22 C20 H20A 120.2 . .
C25 C20 H20A 119.9 . .
C18 C19 C3 119.3(2) . .
C18 C19 C15 121.0(2) . .
C3 C19 C15 119.7(2) . .
C11 C18 C19 119.4(2) . .
C11 C18 C17 121.3(2) . .
C19 C18 C17 119.4(2) . .
N1 C17 C14 121.9(2) . .
N1 C17 C18 118.4(2) . .
C14 C17 C18 119.7(2) . .
C7 C16 C15 119.9(2) . .
C7 C16 C14 121.2(2) . .
C15 C16 C14 119.0(2) . .
C16 C15 C6 118.8(2) . .
C16 C15 C19 121.3(2) . .
C6 C15 C19 119.9(2) . .
N2 C14 C17 121.7(2) . .
N2 C14 C16 118.8(2) . .
C17 C14 C16 119.5(2) . .
N2 C13 C10 119.7(2) . .
N2 C13 C12 120.93(19) . .
C10 C13 C12 119.3(2) . .
N1 C12 C10 119.3(2) . 3_785
N1 C12 C13 120.9(2) . .
C10 C12 C13 119.7(2) 3_785 .
C18 C11 C2 121.0(2) . .
C18 C11 H11A 119.4 . .
C2 C11 H11A 119.6 . .
C13 C10 C12 120.9(2) . 3_785
C13 C10 H10A 119.5 . .
C12 C10 H10A 119.6 3_785 .
C1 C9 C6 121.0(2) . .
C1 C9 H9A 119.5 . .
C6 C9 H9A 119.5 . .
C2 C8 C3 120.9(2) . .
C2 C8 H8A 119.8 . .
C3 C8 H8A 119.3 . .
C16 C7 C1 120.6(2) . .
C16 C7 H7A 119.8 . .
C1 C7 H7A 119.6 . .
C9 C6 C15 119.4(2) . .
C9 C6 C5 122.4(3) . .
C15 C6 C5 118.2(3) . .
C4 C5 C6 122.0(3) . .
C4 C5 H5A 119.1 . .
C6 C5 H5A 118.8 . .
C5 C4 C3 121.4(2) . .
C5 C4 H4A 119.2 . .
C3 C4 H4A 119.3 . .
C8 C3 C19 119.0(2) . .
C8 C3 C4 122.2(2) . .
C19 C3 C4 118.8(3) . .
C8 C2 C11 120.3(3) . .
C8 C2 H2A 119.8 . .
C11 C2 H2A 119.9 . .
C9 C1 C7 120.3(3) . .
C9 C1 H1A 119.8 . .
C7 C1 H1A 119.8 . .
C38 N4 C37 117.4(2) . .
C30 N3 C34 117.1(2) . .
C14 N2 C13 117.3(2) . .
C17 N1 C12 117.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C38 N4 1.317(3) .
C38 C30 1.447(3) .
C38 C35 1.456(3) .
C37 N4 1.369(3) .
C37 C33 1.387(3) .
C37 C34 1.425(3) .
C36 C35 1.412(3) .
C36 C28 1.419(3) .
C36 C29 1.437(3) .
C35 C25 1.381(3) .
C34 N3 1.367(3) .
C34 C33 1.388(3) 3_665
C33 C34 1.388(3) 3_665
C33 H33A 0.9300 .
C32 C24 1.385(3) .
C32 C29 1.413(3) .
C32 C30 1.462(3) .
C31 C23 1.393(3) .
C31 C29 1.415(3) .
C31 C26 1.431(4) .
C30 N3 1.317(3) .
C28 C22 1.396(4) .
C28 C27 1.432(4) .
C27 C26 1.334(4) .
C27 H27A 0.9309 .
C26 H26A 0.9294 .
C25 C20 1.387(3) .
C25 H25A 0.9337 .
C24 C21 1.388(3) .
C24 H24A 0.9330 .
C23 C21 1.364(4) .
C23 H23A 0.9294 .
C22 C20 1.368(4) .
C22 H22A 0.9299 .
C21 H21A 0.9314 .
C20 H20A 0.9337 .
C19 C18 1.409(3) .
C19 C3 1.417(3) .
C19 C15 1.432(3) .
C18 C11 1.382(3) .
C18 C17 1.462(3) .
C17 N1 1.315(3) .
C17 C14 1.449(3) .
C16 C7 1.380(3) .
C16 C15 1.417(3) .
C16 C14 1.465(3) .
C15 C6 1.417(3) .
C14 N2 1.314(3) .
C13 N2 1.368(3) .
C13 C10 1.388(3) .
C13 C12 1.428(3) .
C12 N1 1.368(3) .
C12 C10 1.389(3) 3_785
C11 C2 1.383(3) .
C11 H11A 0.9298 .
C10 C12 1.389(3) 3_785
C10 H10A 0.9325 .
C9 C1 1.369(4) .
C9 C6 1.392(4) .
C9 H9A 0.9332 .
C8 C2 1.366(4) .
C8 C3 1.396(4) .
C8 H8A 0.9306 .
C7 C1 1.388(4) .
C7 H7A 0.9327 .
C6 C5 1.435(3) .
C5 C4 1.333(4) .
C5 H5A 0.9337 .
C4 C3 1.430(4) .
C4 H4A 0.9314 .
C2 H2A 0.9304 .
C1 H1A 0.9351 .
