#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:38:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180271 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/57/7115769.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_7115769
loop_
_publ_author_name
'Cooper W. Johnston'
'Travis R. Schwantje'
'Michael J. Ferguson'
'Robert McDonald'
'Robin G. Hicks'
_publ_section_title
;
 Metal coordination, and metal-ligand redox non-innocence, modulates
 allosteric C-N bond homolysis in an N-benzyl tetrazine
;
_journal_name_full               Chem.Commun.
_journal_page_first              12542
_journal_paper_doi               10.1039/C4cc06235C
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H25 N5 O'
_chemical_formula_sum            'C20 H25 N5 O'
_chemical_formula_weight         351.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.1493(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0802(8)
_cell_length_b                   9.8139(8)
_cell_length_c                   19.8569(15)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.31
_cell_volume                     1964.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17156
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0410
_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)+(0.0479P)²+0.5432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                3693
_reflns_number_total             4513
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4cc06235c2.cif
_cod_data_source_block           vic1011
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7115769
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O 0.10425(10) 0.19061(9) 0.26162(4) 0.0440(2) Uani 1 1 d .
N1 N 0.23688(10) 0.34356(10) 0.11465(5) 0.0302(2) Uani 1 1 d .
N2 N 0.20852(10) 0.32332(10) 0.18389(5) 0.0315(2) Uani 1 1 d .
N3 N 0.12303(10) 0.11234(10) 0.15405(5) 0.0327(2) Uani 1 1 d .
N4 N 0.20724(10) 0.10650(10) 0.09871(5) 0.0319(2) Uani 1 1 d .
N5 N 0.40599(11) 0.33815(12) 0.00554(5) 0.0398(3) Uani 1 1 d .
C1 C 0.14180(12) 0.20754(12) 0.20386(6) 0.0316(2) Uani 1 1 d .
C2 C 0.25703(11) 0.22033(11) 0.07996(5) 0.0290(2) Uani 1 1 d .
C3 C 0.30672(13) 0.38181(15) 0.23089(6) 0.0411(3) Uani 1 1 d .
H3 H 0.2817 0.3522 0.2773 0.049 Uiso 1 1 calc R
C4 C 0.3003(2) 0.53582(17) 0.22914(8) 0.0683(5) Uani 1 1 d .
H4A H 0.2095 0.5656 0.2386 0.082 Uiso 1 1 calc R
H4B H 0.3269 0.5682 0.1845 0.082 Uiso 1 1 calc R
H4C H 0.3606 0.5733 0.2632 0.082 Uiso 1 1 calc R
C5 C 0.44321(17) 0.3264(3) 0.21671(9) 0.0870(7) Uani 1 1 d .
H5A H 0.4409 0.2266 0.2183 0.104 Uiso 1 1 calc R
H5B H 0.5056 0.3603 0.2507 0.104 Uiso 1 1 calc R
H5C H 0.4719 0.3561 0.1719 0.104 Uiso 1 1 calc R
C6 C 0.05753(12) -0.01834(12) 0.16968(6) 0.0349(3) Uani 1 1 d .
H6 H 0.0076 -0.0063 0.2127 0.042 Uiso 1 1 calc R
C7 C -0.04230(14) -0.05170(15) 0.11507(7) 0.0463(3) Uani 1 1 d .
H7A H -0.1067 0.0227 0.1113 0.056 Uiso 1 1 calc R
H7B H -0.0886 -0.1364 0.1265 0.056 Uiso 1 1 calc R
H7C H 0.0038 -0.0630 0.0720 0.056 Uiso 1 1 calc R
C8 C 0.15847(15) -0.13086(14) 0.18060(8) 0.0511(4) Uani 1 1 d .
H8A H 0.2185 -0.1053 0.2174 0.061 Uiso 1 1 calc R
H8B H 0.2097 -0.1443 0.1393 0.061 Uiso 1 1 calc R
H8C H 0.1124 -0.2156 0.1922 0.061 Uiso 1 1 calc R
C9 C 0.14628(12) 0.44181(12) 0.08086(6) 0.0343(3) Uani 1 1 d .
H9A H 0.1785 0.4577 0.0345 0.041 Uiso 1 1 calc R
H9B H 0.1507 0.5298 0.1051 0.041 Uiso 1 1 calc R
C10 C 0.00384(12) 0.39696(12) 0.07740(6) 0.0331(3) Uani 1 1 d .
C11 C -0.03876(13) 0.30650(12) 0.02804(6) 0.0368(3) Uani 1 1 d .
H11 H 0.0227 0.2742 -0.0045 0.044 Uiso 1 1 calc R
C12 C -0.16889(14) 0.26273(16) 0.02544(7) 0.0497(4) Uani 1 1 d .
H12 H -0.1963 0.2004 -0.0085 0.060 Uiso 1 1 calc R
C13 C -0.25858(16) 0.3095(2) 0.07205(9) 0.0689(5) Uani 1 1 d .
H13 H -0.3480 0.2791 0.0707 0.083 Uiso 1 1 calc R
C14 C -0.21852(17) 0.4004(3) 0.12060(9) 0.0803(7) Uani 1 1 d .
H14 H -0.2808 0.4332 0.1526 0.096 Uiso 1 1 calc R
C15 C -0.08793(15) 0.44462(19) 0.12340(7) 0.0566(4) Uani 1 1 d .
H15 H -0.0614 0.5079 0.1570 0.068 Uiso 1 1 calc R
C16 C 0.34139(11) 0.22217(12) 0.01854(5) 0.0307(2) Uani 1 1 d .
C17 C 0.34982(15) 0.10813(14) -0.02235(7) 0.0448(3) Uani 1 1 d .
H17 H 0.3016 0.0278 -0.0118 0.054 Uiso 1 1 calc R
C18 C 0.42961(16) 0.11332(17) -0.07878(7) 0.0542(4) Uani 1 1 d .
H18 H 0.4380 0.0363 -0.1074 0.065 Uiso 1 1 calc R
C19 C 0.49683(14) 0.23230(17) -0.09271(7) 0.0477(3) Uani 1 1 d .
H19 H 0.5524 0.2389 -0.1311 0.057 Uiso 1 1 calc R
C20 C 0.48191(14) 0.34125(16) -0.04991(7) 0.0460(3) Uani 1 1 d .
H20 H 0.5278 0.4232 -0.0601 0.055 Uiso 1 1 calc R
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
C2 N1 N2 112.57(8)
C2 N1 C9 115.20(9)
N2 N1 C9 113.76(9)
C1 N2 N1 119.57(9)
C1 N2 C3 117.75(10)
N1 N2 C3 114.97(9)
C1 N3 N4 120.90(9)
C1 N3 C6 120.04(9)
N4 N3 C6 113.86(9)
C2 N4 N3 115.73(9)
C16 N5 C20 117.16(11)
O C1 N3 122.81(11)
O C1 N2 122.36(11)
N3 C1 N2 114.82(10)
N4 C2 N1 123.40(10)
N4 C2 C16 118.30(10)
N1 C2 C16 118.31(9)
N2 C3 C5 110.66(13)
N2 C3 C4 110.23(12)
C5 C3 C4 113.27(16)
N3 C6 C7 109.53(10)
N3 C6 C8 111.25(10)
C7 C6 C8 112.93(12)
N1 C9 C10 114.60(9)
C15 C10 C11 118.41(13)
C15 C10 C9 120.75(12)
C11 C10 C9 120.84(11)
C12 C11 C10 121.12(13)
C13 C12 C11 119.81(15)
C14 C13 C12 119.80(15)
C13 C14 C15 120.59(15)
C10 C15 C14 120.26(16)
N5 C16 C17 122.95(11)
N5 C16 C2 116.62(10)
C17 C16 C2 120.42(10)
C18 C17 C16 118.83(12)
C19 C18 C17 118.77(14)
C20 C19 C18 118.71(12)
N5 C20 C19 123.57(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C1 1.2201(14)
N1 C2 1.4068(15)
N1 N2 1.4190(13)
N1 C9 1.4869(14)
N2 C1 1.3791(15)
N2 C3 1.4749(16)
N3 C1 1.3734(15)
N3 N4 1.3914(13)
N3 C6 1.4759(14)
N4 C2 1.2804(14)
N5 C16 1.3368(15)
N5 C20 1.3429(16)
C2 C16 1.4887(15)
C3 C5 1.507(2)
C3 C4 1.513(2)
C6 C7 1.5132(19)
C6 C8 1.5167(18)
C9 C10 1.5031(17)
C10 C15 1.3832(18)
C10 C11 1.3896(17)
C11 C12 1.3811(19)
C12 C13 1.375(2)
C13 C14 1.373(3)
C14 C15 1.387(3)
C16 C17 1.3855(18)
C17 C18 1.3819(18)
C18 C19 1.378(2)
C19 C20 1.374(2)
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
C2 N1 N2 C1 -31.36(14)
C9 N1 N2 C1 102.02(12)
C2 N1 N2 C3 117.37(11)
C9 N1 N2 C3 -109.24(11)
C1 N3 N4 C2 -31.31(15)
C6 N3 N4 C2 174.18(10)
N4 N3 C1 O -154.30(11)
C6 N3 C1 O -1.35(18)
N4 N3 C1 N2 24.67(15)
C6 N3 C1 N2 177.63(10)
N1 N2 C1 O -173.21(11)
C3 N2 C1 O 38.91(17)
N1 N2 C1 N3 7.81(15)
C3 N2 C1 N3 -140.08(11)
N3 N4 C2 N1 4.10(16)
N3 N4 C2 C16 -176.35(9)
N2 N1 C2 N4 25.60(15)
C9 N1 C2 N4 -107.09(13)
N2 N1 C2 C16 -153.95(9)
C9 N1 C2 C16 73.37(13)
C1 N2 C3 C5 92.64(15)
N1 N2 C3 C5 -56.69(16)
C1 N2 C3 C4 -141.27(13)
N1 N2 C3 C4 69.40(14)
C1 N3 C6 C7 135.91(12)
N4 N3 C6 C7 -69.34(13)
C1 N3 C6 C8 -98.54(13)
N4 N3 C6 C8 56.21(14)
C2 N1 C9 C10 67.70(13)
N2 N1 C9 C10 -64.43(13)
N1 C9 C10 C15 98.80(14)
N1 C9 C10 C11 -81.08(14)
C15 C10 C11 C12 -1.24(19)
C9 C10 C11 C12 178.65(11)
C10 C11 C12 C13 0.4(2)
C11 C12 C13 C14 0.5(3)
C12 C13 C14 C15 -0.5(3)
C11 C10 C15 C14 1.2(2)
C9 C10 C15 C14 -178.65(15)
C13 C14 C15 C10 -0.4(3)
C20 N5 C16 C17 -0.12(19)
C20 N5 C16 C2 -179.69(11)
N4 C2 C16 N5 -171.29(11)
N1 C2 C16 N5 8.28(15)
N4 C2 C16 C17 9.13(17)
N1 C2 C16 C17 -171.30(11)
N5 C16 C17 C18 0.8(2)
C2 C16 C17 C18 -179.69(13)
C16 C17 C18 C19 -0.7(2)
C17 C18 C19 C20 0.0(2)
C16 N5 C20 C19 -0.6(2)
C18 C19 C20 N5 0.7(2)
