#------------------------------------------------------------------------------
#$Date: 2019-11-14 02:22:03 +0200 (Thu, 14 Nov 2019) $
#$Revision: 227736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/60/4036057.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_4036057
loop_
_publ_author_name
'Garcia, Rosalva C.'
'Pech, Matthew J.'
'Sommer, Roger D.'
'Gorman, Christopher B.'
_publ_section_title
;
 Synthesis of 5,12-Diazapentacenes and Their Properties.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b01628
_journal_year                    2019
_chemical_formula_moiety         'C32 H38 N4'
_chemical_formula_sum            'C32 H38 N4'
_chemical_formula_weight         478.66
_chemical_name_common            RCG0192a-1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                94.8546(18)
_cell_angle_beta                 96.9690(18)
_cell_angle_gamma                97.109(2)
_cell_formula_units_Z            1
_cell_length_a                   4.6765(2)
_cell_length_b                   8.8636(4)
_cell_length_c                   16.2126(8)
_cell_measurement_reflns_used    146
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      34.0864
_cell_measurement_theta_min      4.6900
_cell_volume                     658.53(5)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25735
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0455
_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)+(0.0577P)²+0.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1197
_reflns_number_gt                2993
_reflns_number_total             4030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01628_si_004.cif
_cod_data_source_block           rds757
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4036057
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
N N1 0.7777(2) 0.75853(10) 0.08657(6) 0.0135(2) Uani d . . 1
N N2 0.8020(2) 1.41391(11) 0.05517(6) 0.0189(2) Uani d . . 1
C C1 0.9331(2) 1.14458(12) 0.01678(6) 0.0115(2) Uani d . . 1
C C2 0.8247(2) 1.02763(12) 0.06162(7) 0.0121(2) Uani d . . 1
H H2 0.705567 1.049667 0.103349 0.015 Uiso calc U R 1
C C3 0.8882(2) 0.87889(12) 0.04628(6) 0.0115(2) Uani d . . 1
C C4 0.8605(2) 1.29435(12) 0.03767(7) 0.0132(2) Uani d . . 1
C C5 0.6505(2) 0.76733(12) 0.16087(7) 0.0125(2) Uani d . . 1
C C6 0.7478(3) 0.88086(13) 0.22681(7) 0.0148(2) Uani d . . 1
H H6 0.90056 0.959279 0.221593 0.018 Uiso calc U R 1
C C7 0.6216(3) 0.87931(13) 0.29998(7) 0.0156(2) Uani d . . 1
H H7 0.68778 0.958386 0.343903 0.019 Uiso calc U R 1
C C8 0.4003(2) 0.76483(13) 0.31077(7) 0.0150(2) Uani d . . 1
C C9 0.3072(3) 0.65221(13) 0.24470(7) 0.0168(2) Uani d . . 1
H H9 0.156875 0.572796 0.250372 0.02 Uiso calc U R 1
C C10 0.4282(2) 0.65274(13) 0.17065(7) 0.0147(2) Uani d . . 1
H H10 0.359076 0.574634 0.126409 0.018 Uiso calc U R 1
C C11 0.2706(3) 0.76168(15) 0.39145(7) 0.0188(2) Uani d . . 1
H H11A 0.107648 0.677027 0.384843 0.023 Uiso calc U R 1
H H11B 0.189559 0.858351 0.402402 0.023 Uiso calc U R 1
C C12 0.4864(3) 0.74141(15) 0.46692(7) 0.0199(2) Uani d . . 1
H H12A 0.581265 0.649893 0.454256 0.024 Uiso calc U R 1
H H12B 0.639306 0.831162 0.47725 0.024 Uiso calc U R 1
C C13 0.3424(3) 0.72370(14) 0.54568(7) 0.0181(2) Uani d . . 1
H H13A 0.216016 0.804531 0.551894 0.022 Uiso calc U R 1
H H13B 0.216898 0.623801 0.538957 0.022 Uiso calc U R 1
C C14 0.5569(3) 0.73313(14) 0.62496(7) 0.0182(2) Uani d . . 1
H H14A 0.67279 0.835841 0.633987 0.022 Uiso calc U R 1
H H14B 0.69245 0.657269 0.617284 0.022 Uiso calc U R 1
C C15 0.4118(3) 0.70415(14) 0.70252(7) 0.0177(2) Uani d . . 1
H H15A 0.245461 0.763104 0.703264 0.021 Uiso calc U R 1
H H15B 0.334595 0.594365 0.699429 0.021 Uiso calc U R 1
C C16 0.6189(3) 0.74865(14) 0.78342(7) 0.0196(2) Uani d . . 1
H H16A 0.795751 0.700838 0.780141 0.029 Uiso calc U R 1
H H16B 0.524291 0.713734 0.830441 0.029 Uiso calc U R 1
H H16C 0.669673 0.860007 0.791695 0.029 Uiso calc U R 1
H H1 0.784(3) 0.6672(18) 0.0653(9) 0.021(4) Uiso d . . 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
C3 N1 C5 . . 126.94(9)
C3 N1 H1 . . 118.6(10)
C5 N1 H1 . . 114.5(10)
C2 C1 C3 . 2_775 122.84(9)
C2 C1 C4 . . 117.35(9)
C3 C1 C4 2_775 . 119.80(9)
C1 C2 C3 . . 121.20(9)
C1 C2 H2 . . 119.4
C3 C2 H2 . . 119.4
N1 C3 C2 . . 123.39(9)
N1 C3 C1 . 2_775 120.61(9)
C2 C3 C1 . 2_775 115.96(9)
N2 C4 C1 . . 179.33(11)
C10 C5 C6 . . 118.69(10)
C10 C5 N1 . . 118.34(10)
C6 C5 N1 . . 122.87(10)
C7 C6 C5 . . 120.09(10)
C7 C6 H6 . . 120.0
C5 C6 H6 . . 120.0
C6 C7 C8 . . 121.79(11)
C6 C7 H7 . . 119.1
C8 C7 H7 . . 119.1
C9 C8 C7 . . 117.36(10)
C9 C8 C11 . . 121.25(10)
C7 C8 C11 . . 121.38(11)
C10 C9 C8 . . 121.73(10)
C10 C9 H9 . . 119.1
C8 C9 H9 . . 119.1
C9 C10 C5 . . 120.33(11)
C9 C10 H10 . . 119.8
C5 C10 H10 . . 119.8
C8 C11 C12 . . 113.98(10)
C8 C11 H11A . . 108.8
C12 C11 H11A . . 108.8
C8 C11 H11B . . 108.8
C12 C11 H11B . . 108.8
H11A C11 H11B . . 107.7
C13 C12 C11 . . 112.62(10)
C13 C12 H12A . . 109.1
C11 C12 H12A . . 109.1
C13 C12 H12B . . 109.1
C11 C12 H12B . . 109.1
H12A C12 H12B . . 107.8
C14 C13 C12 . . 113.84(10)
C14 C13 H13A . . 108.8
C12 C13 H13A . . 108.8
C14 C13 H13B . . 108.8
C12 C13 H13B . . 108.8
H13A C13 H13B . . 107.7
C13 C14 C15 . . 113.51(10)
C13 C14 H14A . . 108.9
C15 C14 H14A . . 108.9
C13 C14 H14B . . 108.9
C15 C14 H14B . . 108.9
H14A C14 H14B . . 107.7
C16 C15 C14 . . 112.82(10)
C16 C15 H15A . . 109.0
C14 C15 H15A . . 109.0
C16 C15 H15B . . 109.0
C14 C15 H15B . . 109.0
H15A C15 H15B . . 107.8
C15 C16 H16A . . 109.5
C15 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C15 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C3 . 1.3766(13)
N1 C5 . 1.4074(14)
N1 H1 . 0.858(16)
N2 C4 . 1.1481(15)
C1 C2 . 1.3953(14)
C1 C3 2_775 1.4146(14)
C1 C4 . 1.4338(15)
C2 C3 . 1.3954(15)
C2 H2 . 0.95
C5 C10 . 1.3942(15)
C5 C6 . 1.3961(16)
C6 C7 . 1.3877(15)
C6 H6 . 0.95
C7 C8 . 1.3948(16)
C7 H7 . 0.95
C8 C9 . 1.3899(17)
C8 C11 . 1.5081(15)
C9 C10 . 1.3878(15)
C9 H9 . 0.95
C10 H10 . 0.95
C11 C12 . 1.5266(17)
C11 H11A . 0.99
C11 H11B . 0.99
C12 C13 . 1.5245(16)
C12 H12A . 0.99
C12 H12B . 0.99
C13 C14 . 1.5208(17)
C13 H13A . 0.99
C13 H13B . 0.99
C14 C15 . 1.5252(16)
C14 H14A . 0.99
C14 H14B . 0.99
C15 C16 . 1.5243(17)
C15 H15A . 0.99
C15 H15B . 0.99
C16 H16A . 0.98
C16 H16B . 0.98
C16 H16C . 0.98
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
N1 H1 N2 1_545 0.858(16) 2.250(16) 3.0722(14) 160.6(14)
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
C3 C1 C2 C3 2_775 . -0.01(19)
C4 C1 C2 C3 . . -179.03(11)
C5 N1 C3 C2 . . -16.94(18)
C5 N1 C3 C1 . 2_775 165.70(11)
C1 C2 C3 N1 . . -177.47(11)
C1 C2 C3 C1 . 2_775 0.01(18)
C3 N1 C5 C10 . . 147.38(11)
C3 N1 C5 C6 . . -36.21(17)
C10 C5 C6 C7 . . -0.70(16)
N1 C5 C6 C7 . . -177.10(10)
C5 C6 C7 C8 . . 1.13(17)
C6 C7 C8 C9 . . -0.74(17)
C6 C7 C8 C11 . . 178.22(10)
C7 C8 C9 C10 . . -0.05(17)
C11 C8 C9 C10 . . -179.02(11)
C8 C9 C10 C5 . . 0.45(17)
C6 C5 C10 C9 . . -0.08(16)
N1 C5 C10 C9 . . 176.49(10)
C9 C8 C11 C12 . . 115.96(13)
C7 C8 C11 C12 . . -62.97(15)
C8 C11 C12 C13 . . -174.61(10)
C11 C12 C13 C14 . . -169.17(11)
C12 C13 C14 C15 . . -175.93(10)
C13 C14 C15 C16 . . -167.05(10)
