#------------------------------------------------------------------------------
#$Date: 2019-10-28 08:23:29 +0100 (lun 28 de oct de 2019) $
#$Revision: 219800 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010149.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_2010149
loop_
_publ_author_name
'Miller, Douglas C.'
'Ibers, James A.'
_publ_contact_author
;
     Dr. James A. Ibers
     Department of Chemistry
     Northwestern University
     Evanston, IL 60208-3113
;
_publ_section_title
;
 (Ozaphyrin)(TCNQ)~1/2~
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1834
_journal_page_last               1837
_journal_paper_doi               10.1107/S0108270194002866
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         '2(C36 H40 N4 O), C12 H4 N4'
_chemical_formula_structural     (C~36~H~40~N~4~O)2(C~12~H~4~N~4~)
_chemical_formula_sum            'C84 H84 N12 O2'
_chemical_formula_weight         1293.64
_chemical_name_common            (Ozaphyrin)(TCNQ)~1/2~
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                92.679(10)
_cell_angle_beta                 108.491(10)
_cell_angle_gamma                101.262(10)
_cell_formula_units_Z            1
_cell_length_a                   10.104(2)
_cell_length_b                   13.479(3)
_cell_length_c                   13.835(3)
_cell_measurement_reflns_used    47
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      43.21
_cell_measurement_theta_min      3.37
_cell_volume                     1740.5(7)
_computing_cell_refinement       'CELREF (local program)'
_computing_data_collection       'PCPS (Huffman & Streib, 1992)'
_computing_data_reduction        'NUPICK (local program)'
_computing_molecular_graphics    'SHELXTL/PC User's Manual'
_computing_publication_material  ' SHELXL93 and DATABL (local program)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC User's Manual (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measurement_device       Picker
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  'beta filter'
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.540562
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5036
_diffrn_reflns_theta_max         54.00
_diffrn_reflns_theta_min         3.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       'flat block'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.48
_refine_ls_goodness_of_fit_obs   1.64
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.48
_refine_ls_restrained_S_obs      1.64
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_obs          0.0487
_refine_ls_shift/esd_max         0.118
_refine_ls_shift/esd_mean        0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fₒ²)+(0.04Fₒ²)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.122
_refine_ls_wR_factor_obs         0.111
_reflns_number_observed          2990
_reflns_number_total             4223
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            bk1024.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' calc
w = 1/[\s^2^(F~o~^2^)+(0.04F~o~^2^)^2^]' was changed to 'calc'. New
tag '_refine_ls_weighting_details' was created. The value of the new
tag was set to 'w = 1/[\s^2^(F~o~^2^)+(0.04F~o~^2^)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

2019-10-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H42 N6 O'
_cod_original_formula_weight         646.82
_cod_original_formula_moiety         'C36 H40 N4 O , 0,5C12 H4 N4'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1740.5(6)
_cod_database_code               2010149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O(1) 0.0826(2) 0.7167(2) 0.6886(2) 0.0314(6) Uani d . 1 . O
N(1) 0.4300(3) 0.9532(2) 0.8411(2) 0.0302(7) Uani d . 1 . N
H1 0.3719(3) 0.8972(2) 0.8094(2) 0.036 Uiso calc R 1 . H
N(2) 0.1193(3) 1.0163(2) 0.7799(2) 0.0309(7) Uani d . 1 . N
N(3) -0.1104(3) 0.8478(2) 0.6741(2) 0.0310(7) Uani d . 1 . N
H3N -0.0237(3) 0.8805(2) 0.7051(2) 0.037 Uiso calc R 1 . H
N(4) 0.3827(3) 0.7419(2) 0.7787(2) 0.0304(7) Uani d . 1 . N
C(1) 0.5767(3) 0.9661(2) 0.8842(2) 0.0285(8) Uani d . 1 . C
C(2) 0.6322(3) 1.0696(2) 0.9284(2) 0.0298(8) Uani d . 1 . C
C(3) 0.5209(3) 1.1150(2) 0.9116(2) 0.0313(8) Uani d . 1 . C
H3 0.5273(3) 1.1828(2) 0.9328(2) 0.038 Uiso calc R 1 . H
C(4) 0.3911(3) 1.0429(2) 0.8562(2) 0.0294(8) Uani d . 1 . C
C(5) 0.2578(4) 1.0722(2) 0.8280(2) 0.0318(9) Uani d . 1 . C
C(6) 0.2558(4) 1.1774(2) 0.8522(2) 0.0349(9) Uani d . 1 . C
H6 0.3354(4) 1.2299(2) 0.8842(2) 0.042 Uiso calc R 1 . H
C(7) 0.1197(4) 1.1860(2) 0.8206(2) 0.0337(9) Uani d . 1 . C
C(8) 0.0330(4) 1.0849(2) 0.7755(2) 0.0299(8) Uani d . 1 . C
C(9) -0.1161(3) 1.0696(2) 0.7368(2) 0.0317(8) Uani d . 1 . C
H9 -0.1472(3) 1.1287(2) 0.7463(2) 0.038 Uiso calc R 1 . H
C(10) -0.2284(4) 0.9884(3) 0.6879(2) 0.0339(9) Uani d . 1 . C
H10 -0.3186(4) 1.0029(3) 0.6726(2) 0.041 Uiso calc R 1 . H
C(11) -0.2292(3) 0.8874(2) 0.6574(2) 0.0310(8) Uani d . 1 . C
C(12) -0.3511(3) 0.8097(3) 0.6044(2) 0.0327(8) Uani d . 1 . C
C(13) -0.3005(3) 0.7243(3) 0.5900(2) 0.0348(9) Uani d . 1 . C
H13 -0.3566(3) 0.6613(3) 0.5566(2) 0.042 Uiso calc R 1 . H
C(14) -0.1519(3) 0.7474(2) 0.6335(2) 0.0288(8) Uani d . 1 . C
C(15) -0.0599(3) 0.6815(2) 0.6388(2) 0.0303(8) Uani d . 1 . C
C(16) -0.0855(4) 0.5796(2) 0.6023(3) 0.0354(9) Uani d . 1 . C
H16 -0.1738(4) 0.5379(2) 0.5647(3) 0.042 Uiso calc R 1 . H
C(17) 0.0442(3) 0.5516(2) 0.6322(2) 0.0317(8) Uani d . 1 . C
H17 0.0596(3) 0.4873(2) 0.6189(2) 0.038 Uiso calc R 1 . H
C(18) 0.1467(3) 0.6359(2) 0.6853(3) 0.0308(8) Uani d . 1 . C
C(19) 0.2953(3) 0.6520(2) 0.7315(2) 0.0301(8) Uani d . 1 . C
C(20) 0.3739(4) 0.5730(2) 0.7316(3) 0.0353(9) Uani d . 1 . C
H20 0.3354(4) 0.5053(2) 0.7038(3) 0.042 Uiso calc R 1 . H
C(21) 0.5126(4) 0.6159(2) 0.7792(3) 0.0324(8) Uani d . 1 . C
C(22) 0.5170(3) 0.7228(2) 0.8086(2) 0.0299(8) Uani d . 1 . C
C(23) 0.6399(3) 0.7940(2) 0.8580(3) 0.0357(9) Uani d . 1 . C
H23 0.7228(3) 0.7690(2) 0.8732(3) 0.043 Uiso calc R 1 . H
C(24) 0.6632(4) 0.8980(2) 0.8898(3) 0.0358(9) Uani d . 1 . C
H24 0.7596(4) 0.9280(2) 0.9221(3) 0.043 Uiso calc R 1 . H
C(25) 0.7879(3) 1.1169(2) 0.9847(3) 0.0346(9) Uani d . 1 . C
H25A 0.8412(3) 1.1116(2) 0.9381(3) 0.042 Uiso calc R 1 . H
H25B 0.8230(3) 1.0779(2) 1.0407(3) 0.042 Uiso calc R 1 . H
C(26) 0.8187(3) 1.2278(2) 1.0279(3) 0.0402(9) Uani d . 1 . C
H26A 0.7846(3) 1.2676(2) 0.9723(3) 0.048 Uiso calc R 1 . H
H26B 0.7666(3) 1.2338(2) 1.0751(3) 0.048 Uiso calc R 1 . H
C(27) 0.9766(3) 1.2707(3) 1.0832(3) 0.0437(10) Uani d . 1 . C
H27A 0.9912(3) 1.3407(3) 1.1092(3) 0.066 Uiso calc R 1 . H
H27B 1.0284(3) 1.2662(3) 1.0363(3) 0.066 Uiso calc R 1 . H
H27C 1.0104(3) 1.2324(3) 1.1392(3) 0.066 Uiso calc R 1 . H
C(28) 0.0658(4) 1.2822(2) 0.8277(3) 0.0401(9) Uani d . 1 . C
H28A -0.0058(4) 1.2706(2) 0.8613(3) 0.048 Uiso calc R 1 . H
H28B 0.0202(4) 1.2980(2) 0.7590(3) 0.048 Uiso calc R 1 . H
C(29) 0.1858(4) 1.3738(2) 0.8873(3) 0.0469(10) Uani d . 1 . C
H29A 0.2377(4) 1.3556(2) 0.9535(3) 0.056 Uiso calc R 1 . H
H29B 0.2524(4) 1.3897(2) 0.8499(3) 0.056 Uiso calc R 1 . H
C(30) 0.1302(4) 1.4675(3) 0.9037(3) 0.0563(11) Uani d . 1 . C
H30A 0.2090(4) 1.5224(3) 0.9411(3) 0.084 Uiso calc R 1 . H
H30B 0.0658(4) 1.4527(3) 0.9420(3) 0.084 Uiso calc R 1 . H
H30C 0.0805(4) 1.4869(3) 0.8384(3) 0.084 Uiso calc R 1 . H
C(31) -0.5046(3) 0.8190(3) 0.5707(3) 0.0345(9) Uani d . 1 . C
H31A -0.5147(3) 0.8752(3) 0.5296(3) 0.041 Uiso calc R 1 . H
H31B -0.5298(3) 0.8348(3) 0.6308(3) 0.041 Uiso calc R 1 . H
C(32) -0.6073(3) 0.7231(2) 0.5089(3) 0.0369(9) Uani d . 1 . C
H32A -0.5799(3) 0.7056(2) 0.4503(3) 0.044 Uiso calc R 1 . H
H32B -0.6007(3) 0.6675(2) 0.5510(3) 0.044 Uiso calc R 1 . H
C(33) -0.7605(3) 0.7356(3) 0.4717(3) 0.0435(10) Uani d . 1 . C
H33A -0.8221(3) 0.6733(3) 0.4330(3) 0.065 Uiso calc R 1 . H
H33B -0.7679(3) 0.7897(3) 0.4290(3) 0.065 Uiso calc R 1 . H
H33C -0.7886(3) 0.7516(3) 0.5296(3) 0.065 Uiso calc R 1 . H
C(34) 0.6376(3) 0.5673(2) 0.7966(3) 0.0387(9) Uani d . 1 . C
H34A 0.6906(3) 0.5763(2) 0.8695(3) 0.046 Uiso calc R 1 . H
H34B 0.7005(3) 0.6026(2) 0.7626(3) 0.046 Uiso calc R 1 . H
C(35) 0.5988(4) 0.4541(3) 0.7581(3) 0.0564(12) Uani d . 1 . C
H35A 0.5340(4) 0.4187(3) 0.7905(3) 0.068 Uiso calc R 1 . H
H35B 0.5488(4) 0.4449(3) 0.6847(3) 0.068 Uiso calc R 1 . H
C(36) 0.7281(4) 0.4068(3) 0.7800(3) 0.0637(12) Uani d . 1 . C
H36A 0.6976(4) 0.3358(3) 0.7542(3) 0.096 Uiso calc R 1 . H
H36B 0.7769(4) 0.4142(3) 0.8527(3) 0.096 Uiso calc R 1 . H
H36C 0.7918(4) 0.4405(3) 0.7469(3) 0.096 Uiso calc R 1 . H
N(1') 0.7956(3) 0.6656(2) 0.3667(2) 0.0431(8) Uani d . 1 . N
N(2') 0.5029(3) 0.8769(2) 0.3390(2) 0.0412(8) Uani d . 1 . N
C(1') 0.8775(3) 0.9229(2) 0.4462(2) 0.0272(8) Uani d . 1 . C
C(2') 1.0174(3) 0.9021(2) 0.4807(2) 0.0300(8) Uani d . 1 . C
H2' 1.0277(3) 0.8364(2) 0.4671(2) 0.036 Uiso calc R 1 . H
C(3') 0.8651(3) 1.0254(2) 0.4677(2) 0.0300(8) Uani d . 1 . C
H3' 0.7758(3) 1.0418(2) 0.4459(2) 0.036 Uiso calc R 1 . H
C(4') 0.7580(3) 0.8472(2) 0.3956(2) 0.0294(8) Uani d . 1 . C
C(5') 0.7743(3) 0.7452(3) 0.3776(3) 0.0332(8) Uani d . 1 . C
C(6') 0.6167(4) 0.8636(2) 0.3630(2) 0.0288(8) Uani d . 1 . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 4
0 1 2
1 -2 1
-2 -4 -2
3 3 12
-3 2 3
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
_geom_angle_publ_flag
C(15) O(1) C(18) . 106.9(2) y
C(4) N(1) C(1) . 109.9(3) y
C(8) N(2) C(5) . 105.3(3) y
C(11) N(3) C(14) . 109.0(3) y
C(19) N(4) C(22) . 104.6(3) y
C(24) C(1) N(1) . 130.8(3) y
C(24) C(1) C(2) . 122.2(3) y
N(1) C(1) C(2) . 107.0(3) y
C(3) C(2) C(1) . 107.5(3) y
C(3) C(2) C(25) . 127.4(3) y
C(1) C(2) C(25) . 125.1(3) y
C(2) C(3) C(4) . 109.6(3) y
N(1) C(4) C(5) . 133.3(3) y
N(1) C(4) C(3) . 106.0(3) y
C(5) C(4) C(3) . 120.6(3) y
N(2) C(5) C(4) . 131.3(3) y
N(2) C(5) C(6) . 109.8(3) y
C(4) C(5) C(6) . 118.9(3) y
C(7) C(6) C(5) . 108.0(3) y
C(6) C(7) C(8) . 106.6(3) y
C(6) C(7) C(28) . 126.9(3) y
C(8) C(7) C(28) . 126.6(3) y
N(2) C(8) C(9) . 129.9(3) y
N(2) C(8) C(7) . 110.3(3) y
C(9) C(8) C(7) . 119.8(3) y
C(10) C(9) C(8) . 135.7(3) y
C(9) C(10) C(11) . 130.7(3) y
N(3) C(11) C(10) . 125.1(3) y
N(3) C(11) C(12) . 108.4(3) y
C(10) C(11) C(12) . 126.5(3) y
C(13) C(12) C(11) . 106.1(3) y
C(13) C(12) C(31) . 127.2(3) y
C(11) C(12) C(31) . 126.7(3) y
C(12) C(13) C(14) . 109.1(3) y
N(3) C(14) C(13) . 107.4(3) y
N(3) C(14) C(15) . 125.2(3) y
C(13) C(14) C(15) . 127.4(3) y
O(1) C(15) C(16) . 109.2(3) y
O(1) C(15) C(14) . 119.1(3) y
C(16) C(15) C(14) . 131.7(3) y
C(17) C(16) C(15) . 107.2(3) y
C(18) C(17) C(16) . 107.5(3) y
C(17) C(18) O(1) . 109.1(3) y
C(17) C(18) C(19) . 132.3(3) y
O(1) C(18) C(19) . 118.6(3) y
N(4) C(19) C(18) . 124.9(3) y
N(4) C(19) C(20) . 111.9(3) y
C(18) C(19) C(20) . 123.2(3) y
C(21) C(20) C(19) . 107.0(3) y
C(20) C(21) C(22) . 105.3(3) y
C(20) C(21) C(34) . 127.9(3) y
C(22) C(21) C(34) . 126.8(3) y
C(23) C(22) N(4) . 124.6(3) y
C(23) C(22) C(21) . 124.1(3) y
N(4) C(22) C(21) . 111.2(3) y
C(22) C(23) C(24) . 131.4(3) y
C(1) C(24) C(23) . 134.8(3) y
C(2) C(25) C(26) . 114.9(3) y
C(27) C(26) C(25) . 112.2(3) y
C(7) C(28) C(29) . 112.7(3) y
C(30) C(29) C(28) . 112.7(3) y
C(12) C(31) C(32) . 112.8(3) y
C(33) C(32) C(31) . 112.0(3) y
C(21) C(34) C(35) . 114.6(3) y
C(36) C(35) C(34) . 113.0(3) y
C(4') C(1') C(2') . 121.5(3) y
C(4') C(1') C(3') . 120.9(3) y
C(2') C(1') C(3') . 117.6(3) y
C(3') C(2') C(1') 2_776 122.3(3) y
C(2') C(3') C(1') 2_776 120.1(3) y
C(1') C(4') C(6') . 123.4(3) y
C(1') C(4') C(5') . 119.3(3) y
C(6') C(4') C(5') . 117.2(3) y
N(1') C(5') C(4') . 175.9(4) y
N(2') C(6') C(4') . 178.5(4) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(15) . 1.358(4) y
O(1) C(18) . 1.379(4) y
N(1) C(4) . 1.369(4) y
N(1) C(1) . 1.383(4) y
N(2) C(8) . 1.379(4) y
N(2) C(5) . 1.386(4) y
N(3) C(11) . 1.365(4) y
N(3) C(14) . 1.372(4) y
N(4) C(19) . 1.348(4) y
N(4) C(22) . 1.367(4) y
C(1) C(24) . 1.374(4) y
C(1) C(2) . 1.426(4) y
C(2) C(3) . 1.345(4) y
C(2) C(25) . 1.507(4) y
C(3) C(4) . 1.430(4) y
C(4) C(5) . 1.418(4) y
C(5) C(6) . 1.447(4) y
C(6) C(7) . 1.335(4) y
C(7) C(8) . 1.457(4) y
C(7) C(28) . 1.512(4) y
C(8) C(9) . 1.399(4) y
C(9) C(10) . 1.379(4) y
C(10) C(11) . 1.404(4) y
C(11) C(12) . 1.416(4) y
C(12) C(13) . 1.378(4) y
C(12) C(31) . 1.503(4) y
C(13) C(14) . 1.394(4) y
C(14) C(15) . 1.394(4) y
C(15) C(16) . 1.386(4) y
C(16) C(17) . 1.376(4) y
C(17) C(18) . 1.372(4) y
C(18) C(19) . 1.400(4) y
C(19) C(20) . 1.447(4) y
C(20) C(21) . 1.340(4) y
C(21) C(22) . 1.467(4) y
C(21) C(34) . 1.493(4) y
C(22) C(23) . 1.366(4) y
C(23) C(24) . 1.401(4) y
C(25) C(26) . 1.518(4) y
C(26) C(27) . 1.513(4) y
C(28) C(29) . 1.536(5) y
C(29) C(30) . 1.514(5) y
C(31) C(32) . 1.513(4) y
C(32) C(33) . 1.515(4) y
C(34) C(35) . 1.525(4) y
C(35) C(36) . 1.516(5) y
N(1') C(5') . 1.147(4) y
N(2') C(6') . 1.144(4) y
C(1') C(4') . 1.380(4) y
C(1') C(2') . 1.429(4) y
C(1') C(3') . 1.438(4) y
C(2') C(3') 2_776 1.349(4) y
C(3') C(2') 2_776 1.349(4) y
C(4') C(6') . 1.420(5) y
C(4') C(5') . 1.437(5) y
