#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:40:16 +0100 (dom 17 de nov de 2019) $
#$Revision: 230942 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/14/7231449.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_7231449
loop_
_publ_author_name
'Eusterwiemann, Steffen'
'Doerenkamp, Carsten'
'Dresselhaus, Thomas'
'Janka, Oliver'
'Daniliuc, Constantin G.'
'Pöttgen, Rainer'
'Studer, Armido'
'Eckert, Hellmut'
'Neugebauer, Johannes'
_publ_section_title
;
 Ferro- or antiferromagnetism? Heisenberg chains in the crystal structures
 of verdazyl radicals.
;
_journal_issue                   35
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              22902
_journal_page_last               22908
_journal_paper_doi               10.1039/c8cp03332c
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C18 H11 N4 O'
_chemical_formula_weight         299.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_space_group_name_H-M   'C 1 m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2018-08-14 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.640(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2700(8)
_cell_length_b                   16.9544(11)
_cell_length_c                   3.7589(2)
_cell_measurement_reflns_used    2760
_cell_measurement_temperature    104.(2)
_cell_measurement_theta_max      25.0736
_cell_measurement_theta_min      2.4014
_cell_volume                     713.42(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)
;
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      104.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4586
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.40
_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.134
_refine_ls_abs_structure_details
;
Flack x determined using 480 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(9)
_refine_ls_extinction_coef       0.043(5)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1211
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0267
_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)+(0.0248P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                1127
_reflns_number_total             1211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cp03332c2.cif
_cod_data_source_block           stu7889
_cod_depositor_comments
'Adding full bibliography for 7231447--7231450.cif.'
_cod_database_code               7231449
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
N N1 0.68643(15) 0.43156(10) 0.3556(4) 0.0132(5) Uani d . . . 1
N N2 0.57492(16) 0.42930(11) 0.4709(5) 0.0149(5) Uani d . . . 1
O O1 0.83624(19) 0.5 0.1298(6) 0.0191(6) Uani d T P S 1
C C1 0.7437(3) 0.5 0.2694(9) 0.0134(7) Uani d T P S 1
C C2 0.5272(3) 0.5 0.5137(9) 0.0114(7) Uani d T P S 1
C C3 0.4096(3) 0.5 0.6290(8) 0.0150(7) Uani d T P S 1
C C4 0.3109(3) 0.5 0.7192(9) 0.0158(7) Uani d T P S 1
C C5 0.1972(3) 0.5 0.8237(9) 0.0176(7) Uani d T P S 1
C C6 0.0993(3) 0.5 0.9154(10) 0.0234(8) Uani d T P S 1
H H6 0.018(5) 0.5 1.014(15) 0.063(15) Uiso d . P S 1
C C11 0.73794(19) 0.35545(12) 0.3014(6) 0.0149(5) Uani d . . . 1
C C12 0.8548(2) 0.33946(14) 0.4435(6) 0.0174(5) Uani d . . . 1
H H12 0.903 0.3793 0.5646 0.021 Uiso calc U . R 1
C C13 0.8997(2) 0.26428(15) 0.4054(7) 0.0203(6) Uani d . . . 1
H H13 0.9795 0.2525 0.5005 0.024 Uiso calc U . R 1
C C14 0.8289(2) 0.20602(14) 0.2292(7) 0.0219(6) Uani d . . . 1
H H14 0.8602 0.1545 0.2058 0.026 Uiso calc U . R 1
C C15 0.7127(2) 0.22297(14) 0.0874(6) 0.0198(6) Uani d . . . 1
H H15 0.6645 0.183 -0.0338 0.024 Uiso calc U . R 1
C C16 0.6664(2) 0.29797(13) 0.1219(6) 0.0156(5) Uani d . . . 1
H H16 0.5869 0.3099 0.0242 0.019 Uiso calc U . R 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'
O O 0.0106 0.0060 '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
N2 N1 C1 . . 124.37(18)
N2 N1 C11 . . 114.68(16)
C1 N1 C11 . . 120.78(18)
C2 N2 N1 . . 114.2(2)
O1 C1 N1 . 2_565 123.05(13)
O1 C1 N1 . . 123.05(13)
N1 C1 N1 2_565 . 113.9(3)
N2 C2 N2 2_565 . 128.4(3)
N2 C2 C3 2_565 . 115.77(14)
N2 C2 C3 . . 115.77(14)
C4 C3 C2 . . 178.9(4)
C3 C4 C5 . . 179.9(3)
C6 C5 C4 . . 179.7(3)
C5 C6 H6 . . 176.(3)
C16 C11 C12 . . 121.41(19)
C16 C11 N1 . . 118.47(19)
C12 C11 N1 . . 120.04(19)
C13 C12 C11 . . 118.8(2)
C13 C12 H12 . . 120.6
C11 C12 H12 . . 120.6
C12 C13 C14 . . 120.5(2)
C12 C13 H13 . . 119.7
C14 C13 H13 . . 119.7
C15 C14 C13 . . 120.1(2)
C15 C14 H14 . . 120.0
C13 C14 H14 . . 120.0
C16 C15 C14 . . 120.2(2)
C16 C15 H15 . . 119.9
C14 C15 H15 . . 119.9
C15 C16 C11 . . 119.0(2)
C15 C16 H16 . . 120.5
C11 C16 H16 . . 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 N2 . 1.377(2)
N1 C1 . 1.384(2)
N1 C11 . 1.439(3)
N2 C2 . 1.331(2)
O1 C1 . 1.220(4)
C1 N1 2_565 1.384(2)
C2 N2 2_565 1.331(2)
C2 C3 . 1.442(5)
C3 C4 . 1.199(4)
C4 C5 . 1.383(4)
C5 C6 . 1.193(5)
C6 H6 . 1.03(5)
C11 C16 . 1.389(3)
C11 C12 . 1.390(3)
C12 C13 . 1.385(3)
C12 H12 . 0.95
C13 C14 . 1.388(4)
C13 H13 . 0.95
C14 C15 . 1.386(3)
C14 H14 . 0.95
C15 C16 . 1.386(3)
C15 H15 . 0.95
C16 H16 . 0.95
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_4
_geom_torsion
C1 N1 N2 C2 . -3.5(3)
C11 N1 N2 C2 . -178.8(2)
N2 N1 C1 O1 . -171.5(3)
C11 N1 C1 O1 . 3.5(4)
N2 N1 C1 N1 2_565 8.4(4)
C11 N1 C1 N1 2_565 -176.56(17)
N1 N2 C2 N2 2_565 -2.4(4)
N1 N2 C2 C3 . 179.1(2)
N2 N1 C11 C16 . 44.9(3)
C1 N1 C11 C16 . -130.5(3)
N2 N1 C11 C12 . -131.74(19)
C1 N1 C11 C12 . 52.8(3)
C16 C11 C12 C13 . -0.3(3)
N1 C11 C12 C13 . 176.2(2)
C11 C12 C13 C14 . -0.2(3)
C12 C13 C14 C15 . 0.5(4)
C13 C14 C15 C16 . -0.2(3)
C14 C15 C16 C11 . -0.3(3)
C12 C11 C16 C15 . 0.6(3)
N1 C11 C16 C15 . -176.04(18)
