#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:13:33 +0200 (Fri 07 de Oct de 2022) $
#$Revision: 278463 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/56/7245631.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_7245631
loop_
_publ_author_name
'Chavez, David E.'
'Tappan, Bryce C.'
'Kuehl, Valerie A.'
'Schmalzer, Andrew M.'
'Leonard, Philip W.'
'Wu, Ruilian'
'Imler, Greg H.'
'Parrish, Damon A.'
_publ_section_title
;
 [3+2] click chemistry approach to tetrazine containing polymers
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              28490
_journal_page_last               28493
_journal_paper_doi               10.1039/D2RA05339J
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C8 H6 N4 O2'
_chemical_formula_sum            'C8 H6 N4 O2'
_chemical_formula_weight         190.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-29 deposited with the CCDC.	2022-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5330(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5211(4)
_cell_length_b                   6.8626(3)
_cell_length_c                   7.5560(4)
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.102
_cell_measurement_theta_min      2.450
_cell_volume                     432.93(4)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Photon 100'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'HELIOS multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         2.439
_diffrn_source                   '1uS microfocus'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0369
_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)+(0.0512P)²+0.0659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                946
_reflns_number_total             1223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05339j2.cif
_cod_data_source_block           chav180
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245631
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_file
;

    chav180.res created by SHELXL-2014/7


TITL chav180 in P2(1)/c
CELL  0.71073   8.5211   6.8626   7.5560   90.000  101.533   90.000
ZERR    2.000   0.0004   0.0003   0.0004    0.000    0.001    0.000
LATT 1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  N  O
UNIT 16  12  8  4
L.S. 10
ACTA
CONF
SIZE 0.253 0.247 0.028
BOND $H
FMAP 2
PLAN 20
TEMP 20.000
HTAB
WGHT    0.051200    0.065900
FVAR       0.55310
C1    1    0.961831    0.215861    0.870200    11.00000    0.04755    0.05484 =
         0.04936   -0.00618    0.00376    0.01038
AFIX 163
H1    2    1.040248    0.130097    0.848209    11.00000   -1.20000
AFIX   0
C2    1    0.862757    0.324220    0.897983    11.00000    0.03817    0.04332 =
         0.03406    0.00079    0.00011   -0.00012
C3    1    0.742008    0.458038    0.937710    11.00000    0.03637    0.05197 =
         0.03608   -0.00332   -0.00036    0.00514
AFIX  23
H3A   2    0.767760    0.589374    0.905546    11.00000   -1.20000
H3B   2    0.743275    0.455792    1.066347    11.00000   -1.20000
AFIX   0
O4    4    0.582412    0.407075    0.839278    11.00000    0.03237    0.06126 =
         0.03851    0.00856    0.00414   -0.00119
C5    1    0.544521    0.456107    0.665115    11.00000    0.02771    0.03236 =
         0.03789    0.00208    0.00562    0.00185
N6    3    0.394461    0.410345    0.586852    11.00000    0.02919    0.04194 =
         0.04315    0.00614    0.00571   -0.00460
N7    3    0.347981    0.456533    0.414197    11.00000    0.02707    0.04023 =
         0.04158    0.00350    0.00391   -0.00369

HKLF 4

REM  chav180 in P2(1)/c
REM R1 =  0.0369 for     946 Fo > 4sig(Fo)  and  0.0494 for all    1223 data
REM     64 parameters refined using      0 restraints

END

WGHT      0.0502      0.0680

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, y+1/2, -z+3/2
HTAB C3 N6_$1

REM Highest difference peak  0.190,  deepest hole -0.190,  1-sigma level  0.039
Q1    1   0.8645  0.2108  0.8759  11.00000  0.05    0.19
Q2    1   0.4798  0.4205  0.6126  11.00000  0.05    0.13
Q3    1   0.9572  0.3362  0.9064  11.00000  0.05    0.13
Q4    1   0.5809  0.5198  0.6293  11.00000  0.05    0.13
Q5    1   0.7046  0.3906  1.0648  11.00000  0.05    0.13
Q6    1   0.3975  0.5147  0.3849  11.00000  0.05    0.13
Q7    1   0.9335  0.3429  0.8666  11.00000  0.05    0.13
Q8    1   0.7316  0.6096  0.9603  11.00000  0.05    0.12
Q9    1   0.2627  0.4281  0.3671  11.00000  0.05    0.12
Q10   1   0.7963  0.3483  0.9019  11.00000  0.05    0.11
Q11   1   1.1366 -0.0301  0.9202  11.00000  0.05    0.09
Q12   1   0.6645  0.4467  0.8849  11.00000  0.05    0.09
Q13   1   1.0235  0.4096  0.8291  11.00000  0.05    0.08
Q14   1   0.9183  0.3930  0.7437  11.00000  0.05    0.08
Q15   1   0.3517  0.3282  0.6440  11.00000  0.05    0.08
Q16   1   0.9770 -0.0865  0.8312  11.00000  0.05    0.08
Q17   1   0.8765  0.1644  1.1250  11.00000  0.05    0.08
Q18   1   0.7759  0.6611  1.0816  11.00000  0.05    0.08
Q19   1   0.7843  0.6485  1.2025  11.00000  0.05    0.07
Q20   1   0.9376  0.0203  0.8530  11.00000  0.05    0.07
;
_shelx_res_checksum              48857
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.96183(16) 0.2159(2) 0.87020(18) 0.0514(3) Uani 1 1 d . . . . .
H1 H 1.0402 0.1301 0.8482 0.062 Uiso 1 1 calc R U . . .
C2 C 0.86276(13) 0.32422(17) 0.89798(15) 0.0395(3) Uani 1 1 d . . . . .
C3 C 0.74201(13) 0.45804(18) 0.93771(15) 0.0425(3) Uani 1 1 d . . . . .
H3A H 0.7678 0.5894 0.9055 0.051 Uiso 1 1 calc R U . . .
H3B H 0.7433 0.4558 1.0663 0.051 Uiso 1 1 calc R U . . .
O4 O 0.58241(9) 0.40708(14) 0.83928(11) 0.0445(2) Uani 1 1 d . . . . .
C5 C 0.54452(12) 0.45611(15) 0.66511(14) 0.0328(2) Uani 1 1 d . . . . .
N6 N 0.39446(11) 0.41035(14) 0.58685(13) 0.0383(2) Uani 1 1 d . . . . .
N7 N 0.34798(10) 0.45653(14) 0.41420(13) 0.0367(2) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0476(7) 0.0548(7) 0.0494(7) -0.0062(6) 0.0038(5) 0.0104(6)
C2 0.0382(6) 0.0433(6) 0.0341(5) 0.0008(4) 0.0001(4) -0.0001(5)
C3 0.0364(6) 0.0520(7) 0.0361(6) -0.0033(5) -0.0004(4) 0.0051(5)
O4 0.0324(4) 0.0613(5) 0.0385(4) 0.0086(4) 0.0041(3) -0.0012(3)
C5 0.0277(5) 0.0324(5) 0.0379(5) 0.0021(4) 0.0056(4) 0.0018(4)
N6 0.0292(5) 0.0419(5) 0.0432(5) 0.0061(4) 0.0057(4) -0.0046(4)
N7 0.0271(4) 0.0402(5) 0.0416(5) 0.0035(4) 0.0039(3) -0.0037(3)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 180.0 . . ?
C1 C2 C3 178.41(12) . . ?
C2 C3 O4 111.71(9) . . ?
C2 C3 H3A 109.3 . . ?
O4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
O4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 O4 C3 117.41(9) . . ?
N7 C5 O4 120.29(9) 3_666 . ?
N7 C5 N6 126.17(10) 3_666 . ?
O4 C5 N6 113.53(9) . . ?
N7 N6 C5 116.85(9) . . ?
N6 N7 C5 116.97(9) . 3_666 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.1750(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.4545(16) . ?
C3 O4 1.4562(13) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.3339(13) . ?
C5 N7 1.3331(14) 3_666 ?
C5 N6 1.3345(13) . ?
N6 N7 1.3239(13) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 O4 C5 -77.89(13) . . . . ?
C3 O4 C5 N7 1.80(16) . . . 3_666 ?
C3 O4 C5 N6 -177.75(9) . . . . ?
N7 C5 N6 N7 -0.16(18) 3_666 . . . ?
O4 C5 N6 N7 179.37(9) . . . . ?
C5 N6 N7 C5 0.14(17) . . . 3_666 ?
