#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:40:16 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230942 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/14/7231447.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_7231447
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            'C19 H19 N4 O Si'
_chemical_formula_weight         347.47
_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                 113.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6565(5)
_cell_length_b                   17.9910(9)
_cell_length_c                   5.8635(3)
_cell_measurement_reflns_used    1274
_cell_measurement_temperature    223.(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      4.08
_cell_volume                     931.90(8)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection
;
Collect (Nonius B.V., 1998)
;
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223.(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4397
_diffrn_reflns_theta_full        28.58
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_min         4.11
_diffrn_source                   MoK\a
_diffrn_source_type              'rotating anode Nonius FR591'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor, 2003)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.172
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0659
_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)+(0.0479P)²+1.3019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                1819
_reflns_number_total             2193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cp03332c2.cif
_cod_data_source_block           stu7092
_cod_depositor_comments
'Adding full bibliography for 7231447--7231450.cif.'
_cod_database_code               7231447
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9245(6) 1.0 0.8141(9) 0.0615(13) Uani d T P S 1.0 . .
N N2 0.7087(5) 0.9335(2) 0.2029(7) 0.0501(9) Uani d . . . 1.0 . .
C C1 0.8459(7) 1.0 0.5924(11) 0.0477(15) Uani d T P S 1.0 A .
C C2 0.6687(7) 1.0 0.0973(12) 0.0452(14) Uani d T P S 1.0 . .
C C3 0.5664(8) 1.0 -0.1622(12) 0.0508(15) Uani d TU P S 1.0 . .
C C4 0.4709(8) 1.0 -0.3732(13) 0.0572(17) Uani d TU P S 1.0 . .
Si Si1 0.3010(2) 1.0 -0.6712(3) 0.0549(5) Uani d TU P S 1.0 . .
C C5 0.3020(9) 0.9154(5) -0.8491(13) 0.092(2) Uani d U . . 1.0 . .
H H5A 0.3879 0.9169 -0.8949 0.138 Uiso calc U . R 1.0 . .
H H5B 0.3095 0.8718 -0.7471 0.138 Uiso calc U . R 1.0 . .
H H5C 0.209 0.913 -0.9987 0.138 Uiso calc U . R 1.0 . .
C C6 0.1397(9) 1.0 -0.5793(14) 0.071(2) Uani d TU P S 1.0 . .
H H6A 0.045(13) 1.0 -0.75(2) 0.106 Uiso d U P S 1.0 . .
H H6B 0.143(8) 1.038(4) -0.448(15) 0.106 Uiso d U . . 1.0 . .
N N1 0.7971(4) 0.9356(2) 0.4541(6) 0.0460(9) Uani d U . D 1.0 . .
C C11 0.8581(11) 0.8650(5) 0.5594(16) 0.052(3) Uani d U P D 0.784(9) A 1
C C12 0.8403(8) 0.8405(4) 0.7678(13) 0.065(2) Uani d U P D 0.784(9) A 1
H H12 0.7911 0.8701 0.8444 0.079 Uiso calc U P R 0.784(9) A 1
C C13 0.8970(12) 0.7706(5) 0.8626(18) 0.090(3) Uani d U P D 0.784(9) A 1
H H13 0.8827 0.7519 1.0012 0.108 Uiso calc U P R 0.784(9) A 1
C C14 0.9722(15) 0.7297(6) 0.757(2) 0.095(3) Uani d U P D 0.784(9) A 1
H H14 1.014 0.6837 0.8272 0.114 Uiso calc U P R 0.784(9) A 1
C C15 0.9883(13) 0.7541(5) 0.548(2) 0.100(3) Uani d U P D 0.784(9) A 1
H H15 1.0384 0.7244 0.4735 0.12 Uiso calc U P R 0.784(9) A 1
C C16 0.9305(10) 0.8231(5) 0.4469(16) 0.076(2) Uani d U P D 0.784(9) A 1
H H16 0.9411 0.8405 0.3036 0.092 Uiso calc U P R 0.784(9) A 1
C C11A 0.832(3) 0.8635(14) 0.586(7) 0.052(10) Uani d U P D 0.216(9) A 2
C C12A 0.968(3) 0.8449(13) 0.777(4) 0.076(8) Uani d U P D 0.216(9) A 2
H H12A 1.0408 0.882 0.8549 0.091 Uiso calc U P R 0.216(9) A 2
C C13A 0.998(3) 0.7721(13) 0.851(6) 0.071(8) Uani d U P D 0.216(9) A 2
H H13A 1.0911 0.7597 0.9808 0.085 Uiso calc U P R 0.216(9) A 2
C C14A 0.895(3) 0.7169(14) 0.739(6) 0.074(8) Uani d U P D 0.216(9) A 2
H H14A 0.9215 0.6666 0.7727 0.088 Uiso calc U P R 0.216(9) A 2
C C15A 0.752(3) 0.7366(14) 0.579(6) 0.097(11) Uani d U P D 0.216(9) A 2
H H15A 0.6736 0.7012 0.5284 0.117 Uiso calc U P R 0.216(9) A 2
C C16A 0.723(3) 0.8081(12) 0.490(5) 0.070(8) Uani d U P D 0.216(9) A 2
H H16A 0.6281 0.8197 0.363 0.084 Uiso calc U P R 0.216(9) A 2
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'
Si Si 0.0817 0.0704 '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
C2 N2 N1 . . 114.4(4)
O1 C1 N1 . 2_575 123.1(2)
O1 C1 N1 . . 123.1(2)
N1 C1 N1 2_575 . 113.8(5)
N2 C2 N2 2_575 . 128.0(6)
N2 C2 C3 2_575 . 116.0(3)
N2 C2 C3 . . 116.0(3)
C4 C3 C2 . . 174.6(8)
C3 C4 Si1 . . 170.1(7)
C6 Si1 C5 . . 111.3(3)
C6 Si1 C5 . 2_575 111.3(3)
C5 Si1 C5 . 2_575 111.0(6)
C6 Si1 C4 . . 104.8(3)
C5 Si1 C4 . . 109.2(3)
C5 Si1 C4 2_575 . 109.2(3)
Si1 C5 H5A . . 109.5
Si1 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
Si1 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
Si1 C6 H6A . . 103.(6)
Si1 C6 H6B . . 116.(4)
H6A C6 H6B . . 118.(6)
N2 N1 C1 . . 124.7(4)
N2 N1 C11 . . 114.1(5)
C1 N1 C11 . . 120.5(5)
N2 N1 C11A . . 116.7(14)
C1 N1 C11A . . 118.4(15)
C16 C11 C12 . . 121.7(7)
C16 C11 N1 . . 118.9(8)
C12 C11 N1 . . 119.4(9)
C11 C12 C13 . . 118.3(8)
C11 C12 H12 . . 120.9
C13 C12 H12 . . 120.9
C14 C13 C12 . . 120.4(8)
C14 C13 H13 . . 119.8
C12 C13 H13 . . 119.8
C13 C14 C15 . . 120.9(8)
C13 C14 H14 . . 119.5
C15 C14 H14 . . 119.5
C14 C15 C16 . . 119.9(9)
C14 C15 H15 . . 120.0
C16 C15 H15 . . 120.0
C11 C16 C15 . . 118.7(8)
C11 C16 H16 . . 120.6
C15 C16 H16 . . 120.6
C12A C11A C16A . . 118.3(19)
C12A C11A N1 . . 125.(2)
C16A C11A N1 . . 116.3(17)
C13A C12A C11A . . 120.(2)
C13A C12A H12A . . 120.2
C11A C12A H12A . . 120.2
C14A C13A C12A . . 121.(2)
C14A C13A H13A . . 119.3
C12A C13A H13A . . 119.3
C15A C14A C13A . . 119.(2)
C15A C14A H14A . . 120.7
C13A C14A H14A . . 120.7
C14A C15A C16A . . 120.(2)
C14A C15A H15A . . 120.0
C16A C15A H15A . . 120.0
C15A C16A C11A . . 121.(2)
C15A C16A H16A . . 119.6
C11A C16A H16A . . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.212(7)
N2 C2 . 1.331(5)
N2 N1 . 1.372(5)
C1 N1 2_575 1.383(5)
C1 N1 . 1.383(5)
C2 N2 2_575 1.331(5)
C2 C3 . 1.441(9)
C3 C4 . 1.208(9)
C4 Si1 . 1.851(7)
Si1 C6 . 1.843(8)
Si1 C5 . 1.848(8)
Si1 C5 2_575 1.848(8)
C5 H5A . 0.97
C5 H5B . 0.97
C5 H5C . 0.97
C6 H6A . 1.06(12)
C6 H6B . 1.02(8)
N1 C11 . 1.431(8)
N1 C11A . 1.48(2)
C11 C16 . 1.365(14)
C11 C12 . 1.373(12)
C12 C13 . 1.395(10)
C12 H12 . 0.94
C13 C14 . 1.349(11)
C13 H13 . 0.94
C14 C15 . 1.365(12)
C14 H14 . 0.94
C15 C16 . 1.392(10)
C15 H15 . 0.94
C16 H16 . 0.94
C11A C12A . 1.383(19)
C11A C16A . 1.39(2)
C12A C13A . 1.375(18)
C12A H12A . 0.94
C13A C14A . 1.372(19)
C13A H13A . 0.94
C14A C15A . 1.366(19)
C14A H14A . 0.94
C15A C16A . 1.372(19)
C15A H15A . 0.94
C16A H16A . 0.94
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
N1 N2 C2 N2 . 2_575 2.9(10)
N1 N2 C2 C3 . . -175.4(6)
C2 N2 N1 C1 . . -1.3(8)
C2 N2 N1 C11 . . -171.3(7)
C2 N2 N1 C11A . . 174.(2)
O1 C1 N1 N2 . . -179.7(6)
N1 C1 N1 N2 2_575 . 0.1(9)
O1 C1 N1 C11 . . -10.3(10)
N1 C1 N1 C11 2_575 . 169.4(7)
O1 C1 N1 C11A . . 5.(2)
N1 C1 N1 C11A 2_575 . -175.(2)
N2 N1 C11 C16 . . 50.1(10)
C1 N1 C11 C16 . . -120.3(8)
N2 N1 C11 C12 . . -128.8(7)
C1 N1 C11 C12 . . 60.8(10)
C16 C11 C12 C13 . . -0.6(12)
N1 C11 C12 C13 . . 178.2(8)
C11 C12 C13 C14 . . 2.4(14)
C12 C13 C14 C15 . . -3.0(19)
C13 C14 C15 C16 . . 2.(2)
C12 C11 C16 C15 . . -0.5(15)
N1 C11 C16 C15 . . -179.3(8)
C14 C15 C16 C11 . . -0.1(17)
N2 N1 C11A C12A . . 142.(4)
C1 N1 C11A C12A . . -42.(5)
N2 N1 C11A C16A . . -30.(5)
C1 N1 C11A C16A . . 145.(3)
C16A C11A C12A C13A . . 5.(6)
N1 C11A C12A C13A . . -167.(4)
C11A C12A C13A C14A . . 0.(6)
C12A C13A C14A C15A . . -10.(6)
C13A C14A C15A C16A . . 14.(6)
C14A C15A C16A C11A . . -8.(6)
C12A C11A C16A C15A . . -1.(6)
N1 C11A C16A C15A . . 171.(3)
