#------------------------------------------------------------------------------
#$Date: 2020-01-22 04:49:08 +0200 (Wed, 22 Jan 2020) $
#$Revision: 247074 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/33/7703336.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_7703336
loop_
_publ_author_name
'Dickie, Tara K. K.'
'MacNeil, Connor S.'
'Hayes, Paul G.'
_publ_section_title
;
 Consecutive N₂ loss from a uranium diphosphazide complex.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              578
_journal_page_last               582
_journal_paper_doi               10.1039/c9dt04517a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C6 H6 N4'
_chemical_formula_sum            'C6 H6 N4'
_chemical_formula_weight         134.15
_chemical_name_systematic        1,2-azidoaniline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-19 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3467(3)
_cell_length_b                   13.1849(3)
_cell_length_c                   4.90129(8)
_cell_measurement_reflns_used    5759
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.2310
_cell_measurement_theta_min      3.9960
_cell_volume                     1314.87(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  28.00   0.50    0.50    --    4.52 -77.00 150.00  176
  2  ω      1.00  71.00   0.50    0.50    --    4.52  38.00 -90.00  140
  3  ω    101.00 170.00   0.50    0.50    --  105.46  45.00  30.00  138
  4  ω    101.00 170.00   0.50    0.50    --  105.46  45.00 -90.00  138
  5  ω     37.00 109.00   0.50    0.50    --  105.46 -94.00 -30.00  144
  6  ω     37.00 109.00   0.50    0.50    --  105.46 -94.00 120.00  144
  7  ω     94.00 171.00   0.50    0.50    --  105.46 125.00-150.00  154
  8  ω     82.00 170.00   0.50    0.50    --  105.46  77.00 150.00  176
  9  ω    -69.00  19.00   0.50    0.50    --   -4.52 -77.00 -30.00  176
 10  ω    -71.00  -1.00   0.50    0.50    --   -4.52 -38.00  60.00  140
 11  ω     92.00 168.00   0.50    0.50    --  105.46  61.00  90.00  152
 12  ω    102.00 145.00   0.50    0.50    --  105.46  30.00-150.00   86
 13  ω     97.00 174.00   0.50    0.50    --  105.46  15.00   0.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at zero, Pilatus 200/300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0060324000
_diffrn_orient_matrix_UB_12      -0.0458293000
_diffrn_orient_matrix_UB_13      -0.2880034000
_diffrn_orient_matrix_UB_21      -0.0753477000
_diffrn_orient_matrix_UB_22      0.0016617000
_diffrn_orient_matrix_UB_23      -0.0291607000
_diffrn_orient_matrix_UB_31      0.0037966000
_diffrn_orient_matrix_UB_32      0.1074945000
_diffrn_orient_matrix_UB_33      -0.1226314000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.446
_diffrn_reflns_theta_min         3.995
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_preparation       'see SI'
_exptl_crystal_recrystallization_method 'see SI'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1371
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.4525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1319
_reflns_number_total             1371
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;

    ph16051.res created by SHELXL-2014/7

TITL ph16051_a.res in Pccn
REM Old TITL PH16051 in Pccn #56
REM SHELXT solution in Pccn
REM R1 0.141, Rweak 0.056, Alpha 0.011, Orientation as input
REM Formula found by SHELXT: C7 N3
CELL 1.54184 20.346682 13.18495 4.901289 90 90 90
ZERR 8 0.000326 0.000284 0.000077 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,-Y,0.5-Z
SFAC C H N
UNIT 48 48 32
SIMU N2 N3
 
L.S. 10
PLAN  8
SIZE 0.2 0.25 0.2
BOND $H
LIST 4
MORE -1
CONF
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\PH16051.hkl">
REM </olex2.extras>
 
WGHT    0.051000    0.452500
EXTI    0.004224
FVAR       7.62771
N1    3    0.703071    0.354212    0.277519    11.00000    0.02224    0.01766 =
         0.02056   -0.00064    0.00234    0.00045
AFIX   7
H1A   2    0.677471    0.302392    0.286946    11.00000   -1.20000
H1B   2    0.720481    0.357053    0.117690    11.00000   -1.20000
AFIX   0
N3    3    0.565368    0.351404    0.850774    11.00000    0.02235    0.01857 =
         0.02289   -0.00144   -0.00114    0.00242
N2    3    0.608523    0.351301    0.671108    11.00000    0.02438    0.01910 =
         0.02312   -0.00049    0.00523    0.00189
N4    3    0.527839    0.341000    1.019160    11.00000    0.02761    0.02709 =
         0.02733    0.00114    0.00596    0.00374
C1    1    0.666823    0.442801    0.325195    11.00000    0.01949    0.01790 =
         0.01967   -0.00231   -0.00410    0.00017
C2    1    0.618601    0.445195    0.529881    11.00000    0.02084    0.01742 =
         0.02034   -0.00138   -0.00353   -0.00060
C4    1    0.597793    0.622043    0.444855    11.00000    0.02745    0.01785 =
         0.03331   -0.00342   -0.00587    0.00510
AFIX  43
H4    2    0.574774    0.681306    0.483018    11.00000   -1.20000
AFIX   0
C3    1    0.584162    0.533694    0.587601    11.00000    0.02207    0.02195 =
         0.02522   -0.00457   -0.00135    0.00211
AFIX  43
H3    2    0.551933    0.533653    0.722148    11.00000   -1.20000
AFIX   0
C6    1    0.679942    0.532599    0.184784    11.00000    0.02391    0.02287 =
         0.02279    0.00131   -0.00143   -0.00025
AFIX  43
H6    2    0.711877    0.533039    0.049035    11.00000   -1.20000
AFIX   0
C5    1    0.646071    0.621388    0.244466    11.00000    0.03096    0.01991 =
         0.03106    0.00392   -0.00538    0.00074
AFIX  43
H5    2    0.655771    0.680656    0.149797    11.00000   -1.20000
AFIX   0
HKLF 4
 
REM  ph16051_a.res in Pccn
REM R1 =  0.0341 for    1319 Fo > 4sig(Fo)  and  0.0354 for all    1371 data
REM     93 parameters refined using      6 restraints
 
END  
     
WGHT      0.0506      0.4533 

REM Highest difference peak  0.226,  deepest hole -0.214,  1-sigma level  0.039
Q1    1   0.6403  0.4422  0.4055  11.00000  0.05    0.23
Q2    1   0.7479  0.3444  0.1597  11.00000  0.05    0.18
Q3    1   0.6639  0.5783  0.2337  11.00000  0.05    0.17
Q4    1   0.6000  0.4905  0.5592  11.00000  0.05    0.16
Q5    1   0.6278  0.6241  0.3643  11.00000  0.05    0.16
Q6    1   0.6791  0.4931  0.2888  11.00000  0.05    0.16
Q7    1   0.5903  0.5659  0.4814  11.00000  0.05    0.15
Q8    1   0.6924  0.2765  0.3446  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0341 for 1319 Fo > 4sig(Fo) and 0.0354 for all 7790 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.23, deepest hole -0.21
  REM Mean Shift 0, Max Shift 0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0354
  REM R1_gt = 0.0341
  REM wR_ref = 0.0943
  REM GOOF = 1.064
  REM Shift_max = 0.001
  REM Shift_mean = 0
  REM Reflections_all = 7790
  REM Reflections_gt = 1319
  REM Parameters = n/a
  REM Hole = -0.21
  REM Peak = 0.23
  REM Flack = n/a

  
;
_cod_data_source_file            c9dt04517a2.cif
_cod_data_source_block           ph16051
_cod_database_code               7703336
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C6 H6 N4 '
_chemical_oxdiff_usercomment     'long red needles '
_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_max   0.864
_shelx_estimated_absorpt_t_min   0.834
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
N2 \\sim N3: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6), C5(H5)
;
_olex2_exptl_crystal_mounting_method 'MitiGen loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.832
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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 0.70307(4) 0.35421(6) 0.27752(18) 0.0202(2) Uani 1 1 d . .
H1A H 0.6775 0.3024 0.2869 0.024 Uiso 1 1 d GR .
H1B H 0.7205 0.3571 0.1177 0.024 Uiso 1 1 d GR .
N3 N 0.56537(4) 0.35140(6) 0.85077(19) 0.0213(2) Uani 1 1 d . U
N2 N 0.60852(4) 0.35130(7) 0.67111(18) 0.0222(2) Uani 1 1 d . U
N4 N 0.52784(5) 0.34100(7) 1.01916(19) 0.0273(3) Uani 1 1 d . .
C1 C 0.66682(5) 0.44280(7) 0.3252(2) 0.0190(2) Uani 1 1 d . .
C2 C 0.61860(5) 0.44519(8) 0.5299(2) 0.0195(2) Uani 1 1 d . .
C4 C 0.59779(5) 0.62204(8) 0.4449(2) 0.0262(3) Uani 1 1 d . .
H4 H 0.5748 0.6813 0.4830 0.031 Uiso 1 1 calc R .
C3 C 0.58416(5) 0.53369(8) 0.5876(2) 0.0231(3) Uani 1 1 d . .
H3 H 0.5519 0.5337 0.7221 0.028 Uiso 1 1 calc R .
C6 C 0.67994(5) 0.53260(8) 0.1848(2) 0.0232(3) Uani 1 1 d . .
H6 H 0.7119 0.5330 0.0490 0.028 Uiso 1 1 calc R .
C5 C 0.64607(5) 0.62139(8) 0.2445(2) 0.0273(3) Uani 1 1 d . .
H5 H 0.6558 0.6807 0.1498 0.033 Uiso 1 1 calc R .
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
N1 0.0222(4) 0.0177(4) 0.0206(4) -0.0006(3) 0.0023(3) 0.0004(3)
N3 0.0223(4) 0.0186(4) 0.0229(5) -0.0014(3) -0.0011(4) 0.0024(3)
N2 0.0244(5) 0.0191(5) 0.0231(5) -0.0005(3) 0.0052(4) 0.0019(3)
N4 0.0276(5) 0.0271(5) 0.0273(5) 0.0011(4) 0.0060(4) 0.0037(4)
C1 0.0195(5) 0.0179(5) 0.0197(5) -0.0023(4) -0.0041(4) 0.0002(4)
C2 0.0208(5) 0.0174(5) 0.0203(5) -0.0014(4) -0.0035(4) -0.0006(4)
C4 0.0275(5) 0.0179(5) 0.0333(6) -0.0034(4) -0.0059(5) 0.0051(4)
C3 0.0221(5) 0.0219(5) 0.0252(5) -0.0046(4) -0.0013(4) 0.0021(4)
C6 0.0239(5) 0.0229(5) 0.0228(5) 0.0013(4) -0.0014(4) -0.0002(4)
C5 0.0310(6) 0.0199(6) 0.0311(6) 0.0039(4) -0.0054(5) 0.0007(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
H1A N1 H1B 109.4
C1 N1 H1A 109.5
C1 N1 H1B 109.4
N4 N3 N2 172.66(10)
N3 N2 C2 116.24(8)
N1 C1 C2 120.39(9)
C6 C1 N1 121.63(9)
C6 C1 C2 117.85(9)
C1 C2 N2 115.20(9)
C3 C2 N2 123.69(9)
C3 C2 C1 121.11(10)
C3 C4 H4 120.2
C3 C4 C5 119.53(10)
C5 C4 H4 120.2
C2 C3 H3 119.9
C4 C3 C2 120.10(10)
C4 C3 H3 119.9
C1 C6 H6 119.5
C5 C6 C1 121.08(10)
C5 C6 H6 119.5
C4 C5 C6 120.32(10)
C4 C5 H5 119.8
C6 C5 H5 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 H1A 0.8604
N1 H1B 0.8606
N1 C1 1.4010(13)
N3 N2 1.2436(12)
N3 N4 1.1327(13)
N2 C2 1.4331(13)
C1 C2 1.4036(15)
C1 C6 1.3952(15)
C2 C3 1.3902(14)
C4 H4 0.9300
C4 C3 1.3868(16)
C4 C5 1.3891(17)
C3 H3 0.9300
C6 H6 0.9300
C6 C5 1.3896(15)
C5 H5 0.9300
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 C1 C2 N2 -2.44(13)
N1 C1 C2 C3 177.23(9)
N1 C1 C6 C5 -176.44(10)
N3 N2 C2 C1 -179.05(9)
N3 N2 C2 C3 1.29(15)
N2 C2 C3 C4 178.73(9)
C1 C2 C3 C4 -0.92(16)
C1 C6 C5 C4 -0.57(16)
C2 C1 C6 C5 -0.40(15)
C3 C4 C5 C6 0.81(16)
C6 C1 C2 N2 -178.53(9)
C6 C1 C2 C3 1.14(15)
C5 C4 C3 C2 -0.07(16)
