#------------------------------------------------------------------------------
#$Date: 2021-07-05 20:05:48 +0200 (lun 05 de jul de 2021) $
#$Revision: 267220 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/06/7060620.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_7060620
loop_
_publ_author_name
'Braun, Vanessa'
'Wurzenberger, Maximilian H. H.'
'Weippert, Valentin'
'Stierstorfer, Jörg'
_publ_section_title
;
 Tailoring the properties of 3d transition metal complexes with different
 N-cycloalkyl-substituted tetrazoles
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11042
_journal_page_last               11050
_journal_paper_doi               10.1039/D1NJ01675J
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C4 H6 N4'
_chemical_formula_sum            'C4 H6 N4'
_chemical_formula_weight         110.13
_chemical_name_common            1-cyclopropyl-5H-tetrazole
_chemical_name_systematic        1-cyclopropyl-5H-tetrazole
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_audit_creation_date             2020-04-08
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-04 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.75(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9091(9)
_cell_length_b                   6.6220(8)
_cell_length_c                   8.103(2)
_cell_measurement_reflns_used    604
_cell_measurement_temperature    112(2)
_cell_measurement_theta_max      30.6150
_cell_measurement_theta_min      3.0510
_cell_volume                     259.61(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Diamond 2.1c, Crystal Impact GbR'
_computing_publication_material  'Microsoft Word 2016'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      112(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00 -44.00   1.00    5.00    --  -28.86-178.00  60.00   52
  2  ω      1.00  83.00   1.00    5.00    --   29.79  37.00   0.00   82
  3  ω     52.00 109.00   1.00    5.00    --   29.79 178.00 150.00   57
  4  ω    -19.00  84.00   1.00    5.00    --   29.79 -19.00-120.00  103
  5  ω    -35.00 106.00   1.00    5.00    --   29.79  19.00 -90.00  141
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0791454000
_diffrn_orient_matrix_UB_12      0.0652377000
_diffrn_orient_matrix_UB_13      -0.0592351000
_diffrn_orient_matrix_UB_21      0.0364076000
_diffrn_orient_matrix_UB_22      -0.0581407000
_diffrn_orient_matrix_UB_23      -0.0663170000
_diffrn_orient_matrix_UB_31      -0.1178577000
_diffrn_orient_matrix_UB_32      -0.0618478000
_diffrn_orient_matrix_UB_33      0.0003758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         3.998
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.75a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             116
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1571
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0434
_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)+(0.0274P)²+0.0286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1319
_reflns_number_total             1571
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01675j2.cif
_cod_data_source_block           px139
_cod_depositor_comments
'Adding full bibliography for 7060620--7060640.cif.'
_cod_original_cell_volume        259.60(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7060620
_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   0.952
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_file
;
TITL px139_a.res in P2(1)
    shelx.res
    created by SHELXL-2018/3 at 17:40:53 on 15-Apr-2020
CELL  0.71073   4.9091   6.6220   8.1027   90.000   99.750   90.000
ZERR     2.00   0.0009   0.0008   0.0021    0.000    0.021    0.000
LATT  -1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N
UNIT  8 12 8
MERG   2
OMIT     0   0   1
MORE -1
SHEL 1000 0.7
EQIV $1 -x+1, y+1/2, -z+2
HTAB C1 N4_$1
FMAP   2
PLAN   20
SIZE     0.138   0.491   0.500
ACTA
HTAB    2.00000
BOND   $H
CONF
LIST   4
L.S.  10
TEMP  -161.15
WGHT    0.027400    0.028600
FVAR       2.24292
N1    3    0.762026    0.508245    0.796075    11.00000    0.02230    0.01561 =
         0.02641   -0.00055    0.00466   -0.00013
N3    3    0.940600    0.215337    0.801881    11.00000    0.02978    0.01892 =
         0.03640   -0.00121    0.00696    0.00200
N2    3    0.955381    0.394958    0.738233    11.00000    0.02787    0.02114 =
         0.03412   -0.00271    0.01132    0.00129
N4    3    0.739371    0.209047    0.900710    11.00000    0.02887    0.02190 =
         0.02924    0.00184    0.00478   -0.00110
C1    1    0.634852    0.392319    0.894318    11.00000    0.02589    0.01986 =
         0.02699    0.00123    0.00714   -0.00144
C2    1    0.726452    0.721242    0.758422    11.00000    0.02508    0.01500 =
         0.02390   -0.00024    0.00276   -0.00203
C3    1    0.445019    0.792742    0.681735    11.00000    0.02728    0.01811 =
         0.03209    0.00364    0.00685    0.00168
C4    1    0.672451    0.785188    0.579359    11.00000    0.03588    0.02265 =
         0.02491    0.00071    0.00874    0.00025
H4A   2    0.763138    0.910801    0.552840    11.00000    0.02323
H3A   2    0.384458    0.921504    0.712622    11.00000    0.02714
H3B   2    0.301397    0.692724    0.662602    11.00000    0.03232
H4B   2    0.666250    0.688445    0.503032    11.00000    0.04004
H2    2    0.837179    0.796113    0.834195    11.00000    0.02241
H1    2    0.487797    0.442057    0.946177    11.00000    0.04105
HKLF    4




REM  px139_a.res in P2(1)
REM wR2 = 0.0941, GooF = S = 1.102, Restrained GooF = 1.101 for all data
REM R1 = 0.0434 for 1319 Fo > 4sig(Fo) and 0.0579 for all 1571 data
REM 97 parameters refined using 1 restraints

END

WGHT      0.0273      0.0288

REM Instructions for potential hydrogen bonds
HTAB C1 N4_$1

REM Highest difference peak  0.208,  deepest hole -0.212,  1-sigma level  0.043
Q1    1   0.5037  0.7974  0.5791  11.00000  0.05    0.21
Q2    1   0.7224  0.6191  0.7722  11.00000  0.05    0.17
Q3    1   1.1139  0.4073  0.7582  11.00000  0.05    0.17
Q4    1   0.4168  0.6594  0.6640  11.00000  0.05    0.16
Q5    1   0.9021  0.2185  0.9299  11.00000  0.05    0.16
Q6    1   0.8481  0.4672  0.7570  11.00000  0.05    0.15
Q7    1   0.8978  0.2893  0.7460  11.00000  0.05    0.15
Q8    1   0.7541  0.3242  0.9113  11.00000  0.05    0.15
Q9    1   0.9057  0.7500  0.7759  11.00000  0.05    0.15
Q10   1   0.7907  0.0742  0.9195  11.00000  0.05    0.14
Q11   1   0.7997  0.7414  0.6633  11.00000  0.05    0.14
Q12   1   0.5927  0.1290  0.8973  11.00000  0.05    0.14
Q13   1   0.7704  0.2993  1.0412  11.00000  0.05    0.14
Q14   1   0.5976  0.4941  0.7449  11.00000  0.05    0.13
Q15   1   0.5862  0.2762  0.8487  11.00000  0.05    0.13
Q16   1   0.0762  0.6312  0.7539  11.00000  0.05    0.13
Q17   1   1.1582  0.2366  0.8293  11.00000  0.05    0.13
Q18   1   0.9925  0.5067  0.6797  11.00000  0.05    0.13
Q19   1   0.8998  0.5459  0.5764  11.00000  0.05    0.13
Q20   1   0.7230  0.5286  0.9160  11.00000  0.05    0.13
;
_shelx_res_checksum              12352
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
N1 N 0.7620(4) 0.5082(3) 0.7961(3) 0.0214(4) Uani 1 1 d . . . . .
N3 N 0.9406(4) 0.2153(3) 0.8019(3) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.9554(4) 0.3950(3) 0.7382(3) 0.0270(5) Uani 1 1 d . . . . .
N4 N 0.7394(4) 0.2090(3) 0.9007(3) 0.0267(5) Uani 1 1 d . . . . .
C1 C 0.6349(5) 0.3923(3) 0.8943(3) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.7265(5) 0.7212(4) 0.7584(3) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.4450(5) 0.7927(4) 0.6817(4) 0.0256(5) Uani 1 1 d . . . . .
C4 C 0.6725(6) 0.7852(4) 0.5794(4) 0.0274(6) Uani 1 1 d . . . . .
H4A H 0.763(5) 0.911(4) 0.553(4) 0.023(7) Uiso 1 1 d . . . . .
H3A H 0.384(5) 0.922(4) 0.713(4) 0.027(7) Uiso 1 1 d . . . . .
H3B H 0.301(6) 0.693(5) 0.663(4) 0.032(8) Uiso 1 1 d . . . . .
H4B H 0.666(6) 0.688(5) 0.503(4) 0.040(9) Uiso 1 1 d . . . . .
H2 H 0.837(5) 0.796(4) 0.834(4) 0.022(7) Uiso 1 1 d . . . . .
H1 H 0.488(7) 0.442(4) 0.946(4) 0.041(9) Uiso 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
N1 0.0223(10) 0.0156(9) 0.0264(11) -0.0006(8) 0.0047(7) -0.0001(8)
N3 0.0298(11) 0.0189(9) 0.0364(13) -0.0012(10) 0.0070(9) 0.0020(9)
N2 0.0279(10) 0.0211(10) 0.0341(12) -0.0027(9) 0.0113(9) 0.0013(9)
N4 0.0289(10) 0.0219(9) 0.0292(12) 0.0018(9) 0.0048(8) -0.0011(9)
C1 0.0259(11) 0.0199(12) 0.0270(12) 0.0012(10) 0.0071(10) -0.0014(10)
C2 0.0251(11) 0.0150(9) 0.0239(12) -0.0002(10) 0.0028(9) -0.0020(10)
C3 0.0273(12) 0.0181(10) 0.0321(14) 0.0036(10) 0.0069(10) 0.0017(10)
C4 0.0359(14) 0.0226(11) 0.0249(14) 0.0007(11) 0.0087(11) 0.0003(11)
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'
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
C1 N1 N2 108.29(19) . . ?
C1 N1 C2 129.4(2) . . ?
N2 N1 C2 122.2(2) . . ?
N2 N3 N4 110.61(19) . . ?
N3 N2 N1 106.2(2) . . ?
C1 N4 N3 105.3(2) . . ?
N4 C1 N1 109.6(2) . . ?
N4 C1 H1 128.4(18) . . ?
N1 C1 H1 122.0(18) . . ?
N1 C2 C4 118.5(2) . . ?
N1 C2 C3 117.8(2) . . ?
C4 C2 C3 60.36(18) . . ?
N1 C2 H2 110.9(18) . . ?
C4 C2 H2 119.7(18) . . ?
C3 C2 H2 121.4(17) . . ?
C2 C3 C4 59.78(17) . . ?
C2 C3 H3A 118.9(17) . . ?
C4 C3 H3A 118.1(18) . . ?
C2 C3 H3B 116.8(17) . . ?
C4 C3 H3B 118.8(17) . . ?
H3A C3 H3B 114(2) . . ?
C2 C4 C3 59.86(17) . . ?
C2 C4 H4A 116.1(17) . . ?
C3 C4 H4A 119.9(15) . . ?
C2 C4 H4B 117(2) . . ?
C3 C4 H4B 118(2) . . ?
H4A C4 H4B 115(2) . . ?
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
N1 C1 1.335(3) . ?
N1 N2 1.354(3) . ?
N1 C2 1.447(3) . ?
N3 N2 1.303(3) . ?
N3 N4 1.374(3) . ?
N4 C1 1.315(3) . ?
C1 H1 0.95(3) . ?
C2 C4 1.491(4) . ?
C2 C3 1.493(3) . ?
C2 H2 0.90(3) . ?
C3 C4 1.500(4) . ?
C3 H3A 0.95(3) . ?
C3 H3B 0.96(3) . ?
C4 H4A 0.98(3) . ?
C4 H4B 0.89(3) . ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
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
C1 H1 N4 0.95(3) 2.53(3) 3.401(3) 153(2) 2_657
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
N4 N3 N2 N1 0.1(3) . . . . ?
C1 N1 N2 N3 0.1(3) . . . . ?
C2 N1 N2 N3 176.8(2) . . . . ?
N2 N3 N4 C1 -0.2(3) . . . . ?
N3 N4 C1 N1 0.3(3) . . . . ?
N2 N1 C1 N4 -0.2(3) . . . . ?
C2 N1 C1 N4 -176.7(2) . . . . ?
C1 N1 C2 C4 -127.9(3) . . . . ?
N2 N1 C2 C4 56.1(3) . . . . ?
C1 N1 C2 C3 -58.3(3) . . . . ?
N2 N1 C2 C3 125.7(2) . . . . ?
N1 C2 C3 C4 -108.7(3) . . . . ?
N1 C2 C4 C3 107.6(2) . . . . ?
