#------------------------------------------------------------------------------
#$Date: 2019-11-23 21:42:08 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 235401 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/63/7236325.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_7236325
loop_
_publ_author_name
'Kumar, Dheeraj'
'Mitchell, Lauren A.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Asymmetric N,N′-ethylene-bridged azole-based compounds: Two way
 control of the energetic properties of compounds
;
_journal_issue                   25
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              9931
_journal_paper_doi               10.1039/C6TA03536A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C6 H6 Cl N9 O4'
_chemical_formula_sum            'C6 H6 Cl N9 O4'
_chemical_formula_weight         303.65
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.094(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.302(7)
_cell_length_b                   5.631(2)
_cell_length_c                   11.142(4)
_cell_measurement_reflns_used    2746
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      3.37
_cell_volume                     1139.5(7)
_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) within WINGX (Farrugia, 2012)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART 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  0.0630
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.377
_diffrn_reflns_theta_min         1.842
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0751
_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)+(0.1422P)²+4.1011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2088
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2042
_reflns_number_total             2537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ta03536a2.cif
_cod_data_source_block           shrv364
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7236325
_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   0.925
_shelx_estimated_absorpt_t_max   0.998
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
N1 N 0.9560(3) 0.8785(10) 0.8387(5) 0.0281(12) Uani 1 1 d . .
H1A H 0.976(4) 1.004(16) 0.872(7) 0.034 Uiso 1 1 d . U
H1B H 0.935(5) 0.900(14) 0.773(8) 0.034 Uiso 1 1 d . U
C2 C 0.9311(3) 0.7275(10) 0.9177(4) 0.0196(10) Uani 1 1 d . .
N3 N 0.9427(3) 0.7410(10) 1.0367(4) 0.0255(10) Uani 1 1 d . .
N4 N 0.9095(3) 0.5485(10) 1.0794(4) 0.0264(11) Uani 1 1 d . .
N5 N 0.8771(3) 0.4211(9) 0.9922(4) 0.0256(11) Uani 1 1 d . .
N6 N 0.8908(3) 0.5309(8) 0.8877(4) 0.0198(9) Uani 1 1 d . .
C7 C 0.8663(3) 0.4257(11) 0.7701(5) 0.0243(12) Uani 1 1 d . .
H7A H 0.8527 0.2577 0.7816 0.029 Uiso 1 1 calc R U
H7B H 0.9075 0.4281 0.7203 0.029 Uiso 1 1 calc R U
C8 C 0.8005(3) 0.5553(10) 0.7026(4) 0.0202(11) Uani 1 1 d . .
H8A H 0.8132 0.7248 0.6939 0.024 Uiso 1 1 calc R U
H8B H 0.7895 0.4872 0.6204 0.024 Uiso 1 1 calc R U
N9 N 0.7347(2) 0.5379(8) 0.7650(4) 0.0178(9) Uani 1 1 d . .
N10 N 0.7225(3) 0.7166(8) 0.8383(4) 0.0197(9) Uani 1 1 d . .
C11 C 0.6575(3) 0.6661(10) 0.8749(5) 0.0205(10) Uani 1 1 d . .
N12 N 0.6291(3) 0.8312(9) 0.9564(4) 0.0248(11) Uani 1 1 d . .
O13 O 0.6694(3) 0.9946(9) 0.9956(4) 0.0355(11) Uani 1 1 d . .
O14 O 0.5660(3) 0.8006(9) 0.9790(5) 0.0396(12) Uani 1 1 d . .
C15 C 0.6261(3) 0.4568(10) 0.8252(5) 0.0207(11) Uani 1 1 d . .
Cl16 Cl 0.54546(8) 0.3304(3) 0.84765(15) 0.0313(4) Uani 1 1 d . .
C17 C 0.6789(3) 0.3784(9) 0.7560(5) 0.0179(10) Uani 1 1 d . .
N18 N 0.6787(3) 0.1646(8) 0.6839(4) 0.0227(10) Uani 1 1 d . .
O19 O 0.6220(3) 0.0526(8) 0.6686(5) 0.0363(11) Uani 1 1 d . .
O20 O 0.7369(2) 0.1082(8) 0.6477(4) 0.0280(9) Uani 1 1 d . .
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'
Cl Cl 0.1484 0.1585 '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 H1A 113(5)
C2 N1 H1B 122(6)
H1A N1 H1B 114(8)
N3 C2 N1 126.6(6)
N3 C2 N6 108.2(5)
N1 C2 N6 125.2(5)
C2 N3 N4 106.4(5)
N5 N4 N3 111.3(4)
N4 N5 N6 105.9(5)
C2 N6 N5 108.2(4)
C2 N6 C7 130.9(5)
N5 N6 C7 120.8(5)
N6 C7 C8 112.7(5)
N6 C7 H7A 109.0
C8 C7 H7A 109.0
N6 C7 H7B 109.0
C8 C7 H7B 109.0
H7A C7 H7B 107.8
N9 C8 C7 112.3(4)
N9 C8 H8A 109.2
C7 C8 H8A 109.2
N9 C8 H8B 109.2
C7 C8 H8B 109.2
H8A C8 H8B 107.9
N10 N9 C17 111.4(4)
N10 N9 C8 116.8(4)
C17 N9 C8 131.7(5)
N9 N10 C11 104.5(4)
N10 C11 C15 113.4(5)
N10 C11 N12 117.4(5)
C15 C11 N12 129.2(5)
O14 N12 O13 125.0(5)
O14 N12 C11 117.5(5)
O13 N12 C11 117.4(5)
C17 C15 C11 102.1(5)
C17 C15 Cl16 129.4(5)
C11 C15 Cl16 128.5(4)
N9 C17 C15 108.6(5)
N9 C17 N18 122.9(5)
C15 C17 N18 128.4(5)
O19 N18 O20 125.8(5)
O19 N18 C17 117.1(5)
O20 N18 C17 117.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.344(7)
N1 H1A 0.86(9)
N1 H1B 0.80(9)
C2 N3 1.319(6)
C2 N6 1.349(7)
N3 N4 1.357(7)
N4 N5 1.292(7)
N5 N6 1.368(6)
N6 C7 1.457(7)
C7 C8 1.525(8)
C7 H7A 0.9900
C7 H7B 0.9900
C8 N9 1.466(7)
C8 H8A 0.9900
C8 H8B 0.9900
N9 N10 1.332(6)
N9 C17 1.354(7)
N10 C11 1.334(7)
C11 C15 1.396(8)
C11 N12 1.441(7)
N12 O14 1.224(7)
N12 O13 1.225(7)
C15 C17 1.381(8)
C15 Cl16 1.685(6)
C17 N18 1.447(7)
N18 O19 1.209(7)
N18 O20 1.226(7)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N3 0.86(9) 2.22(9) 3.053(8) 162(7) 3_777
N1 H1B N4 0.80(9) 2.17(9) 2.937(7) 163(8) 4_575
C7 H7A O20 0.99 2.58 3.141(7) 116.0 .
C8 H8A N4 0.99 2.63 3.394(7) 134.1 4_575
C8 H8A O20 0.99 2.59 3.354(7) 134.0 1_565
C8 H8B O13 0.99 2.45 3.128(7) 125.0 4_575
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
N1 C2 N3 N4 -178.0(6)
N6 C2 N3 N4 0.6(6)
C2 N3 N4 N5 -1.3(7)
N3 N4 N5 N6 1.5(6)
N3 C2 N6 N5 0.3(6)
N1 C2 N6 N5 178.9(6)
N3 C2 N6 C7 -176.3(5)
N1 C2 N6 C7 2.3(10)
N4 N5 N6 C2 -1.1(6)
N4 N5 N6 C7 175.9(5)
C2 N6 C7 C8 -77.6(7)
N5 N6 C7 C8 106.2(6)
N6 C7 C8 N9 -64.7(6)
C7 C8 N9 N10 94.9(5)
C7 C8 N9 C17 -90.7(7)
C17 N9 N10 C11 -0.2(6)
C8 N9 N10 C11 175.3(4)
N9 N10 C11 C15 -0.8(6)
N9 N10 C11 N12 -179.7(4)
N10 C11 N12 O14 171.7(5)
C15 C11 N12 O14 -7.1(8)
N10 C11 N12 O13 -6.8(7)
C15 C11 N12 O13 174.5(5)
N10 C11 C15 C17 1.4(6)
N12 C11 C15 C17 -179.8(5)
N10 C11 C15 Cl16 179.9(4)
N12 C11 C15 Cl16 -1.3(9)
N10 N9 C17 C15 1.1(6)
C8 N9 C17 C15 -173.4(5)
N10 N9 C17 N18 -178.9(4)
C8 N9 C17 N18 6.6(9)
C11 C15 C17 N9 -1.5(6)
Cl16 C15 C17 N9 -179.9(4)
C11 C15 C17 N18 178.5(5)
Cl16 C15 C17 N18 0.0(9)
N9 C17 N18 O19 -169.8(5)
C15 C17 N18 O19 10.2(8)
N9 C17 N18 O20 13.0(7)
C15 C17 N18 O20 -167.0(5)
