#------------------------------------------------------------------------------
#$Date: 2021-03-18 07:29:19 +0200 (Thu, 18 Mar 2021) $
#$Revision: 263108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/24/7242416.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_7242416
loop_
_publ_author_name
'Mittal, Rupali'
'Kumar, Amit'
'Awasthi, Satish Kumar'
_publ_section_title
;
 Practical scale up synthesis of carboxylic acids and their bioisosteres
 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid
 acid carbocatalyst
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              11166
_journal_page_last               11176
_journal_paper_doi               10.1039/D1RA01053K
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C8 H7 Cl N4'
_chemical_formula_sum            'C8 H7 Cl N4'
_chemical_formula_weight         194.63
_chemical_name_systematic        5-(3-chlorobenzyl)-1H-tetrazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-09-14 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.575(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8058(5)
_cell_length_b                   26.6823(19)
_cell_length_c                   7.1899(7)
_cell_measurement_reflns_used    2632
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4860
_cell_measurement_theta_min      3.7240
_cell_volume                     883.65(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_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      0.00  87.00   1.00    2.50    --   18.84  57.00   0.00   87
  2  ω      6.00  87.00   1.00    2.50    --   18.84  57.00 -90.00   81
  3  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00 -60.00   84
  4  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00-150.00   84
  5  ω    -48.00  35.00   1.00    2.50    --   18.84 -57.00   0.00   83
  6  ω    -25.00  59.00   1.00    2.50    --   18.84 -99.00 120.00   84
  7  ω     -6.00  82.00   1.00    2.50    --   18.84  77.00 150.00   88
  8  ω    -82.00  -1.00   1.00    2.50    --  -15.17 -57.00  30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0782383000
_diffrn_orient_matrix_UB_12      0.0220179000
_diffrn_orient_matrix_UB_13      -0.0381814000
_diffrn_orient_matrix_UB_21      0.1269001000
_diffrn_orient_matrix_UB_22      0.0145769000
_diffrn_orient_matrix_UB_23      0.0386433000
_diffrn_orient_matrix_UB_31      0.0383747000
_diffrn_orient_matrix_UB_32      -0.0031717000
_diffrn_orient_matrix_UB_33      -0.0874456000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11098
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.327
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate: Hexane (1:1)'
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0718
_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)+(0.0319P)²+1.0298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1463
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1379
_reflns_number_total             1617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra01053k2.cif
_cod_data_source_block           c
_cod_database_code               7242416
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C8 H7 Cl N4'
_chemical_oxdiff_usercomment     28-08-2019
_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.
;
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C4(H4A)
;
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.591
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl1 Cl 0.1121(3) 0.45591(5) 0.18894(19) 0.0862(5) Uani 1 1 d . . . . .
N4 N 0.9201(6) 0.23754(11) 0.4383(4) 0.0428(7) Uani 1 1 d . . . . .
N1 N 0.6912(6) 0.25972(11) 0.6379(4) 0.0451(7) Uani 1 1 d . . . . .
N3 N 0.8146(7) 0.19534(11) 0.4932(4) 0.0503(8) Uani 1 1 d . . . . .
N2 N 0.6776(7) 0.20895(11) 0.6140(5) 0.0510(8) Uani 1 1 d . . . . .
C8 C 0.8449(7) 0.27680(12) 0.5253(5) 0.0364(8) Uani 1 1 d . . . . .
C1 C 0.7195(7) 0.36872(12) 0.5300(5) 0.0417(8) Uani 1 1 d . . . . .
C2 C 0.5350(8) 0.39186(13) 0.3700(5) 0.0479(9) Uani 1 1 d . . . . .
H2 H 0.538831 0.382940 0.245671 0.057 Uiso 1 1 calc R . . . .
C6 C 0.7087(8) 0.38282(14) 0.7142(5) 0.0478(9) Uani 1 1 d . . . . .
H6 H 0.831013 0.367581 0.823558 0.057 Uiso 1 1 calc R . . . .
C7 C 0.9315(8) 0.32943(13) 0.5046(6) 0.0495(9) Uani 1 1 d . . . . .
H7A H 0.958737 0.333429 0.376833 0.059 Uiso 1 1 calc R . . . .
H7B H 1.117342 0.335534 0.599316 0.059 Uiso 1 1 calc R . . . .
C5 C 0.5172(9) 0.41929(15) 0.7345(6) 0.0557(10) Uani 1 1 d . . . . .
H5 H 0.511491 0.428606 0.858045 0.067 Uiso 1 1 calc R . . . .
C3 C 0.3462(8) 0.42803(14) 0.3951(6) 0.0510(9) Uani 1 1 d . . . . .
C4 C 0.3328(8) 0.44232(14) 0.5737(6) 0.0536(10) Uani 1 1 d . . . . .
H4A H 0.203133 0.466926 0.587543 0.064 Uiso 1 1 calc R . . . .
H4 H 1.010(9) 0.2366(15) 0.353(6) 0.063(13) Uiso 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'
Cl Cl 0.1484 0.1585 '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
N3 N4 H4 120(3) . . ?
C8 N4 N3 110.4(3) . . ?
C8 N4 H4 129(3) . . ?
C8 N1 N2 106.2(3) . . ?
N2 N3 N4 105.8(3) . . ?
N3 N2 N1 110.5(3) . . ?
N4 C8 C7 125.4(3) . . ?
N1 C8 N4 107.0(3) . . ?
N1 C8 C7 127.5(3) . . ?
C2 C1 C6 118.9(3) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 120.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C1 115.3(3) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C1 C7 H7A 108.5 . . ?
C1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C6 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C4 C5 H5 119.5 . . ?
C2 C3 Cl1 118.5(3) . . ?
C4 C3 Cl1 119.3(3) . . ?
C4 C3 C2 122.2(4) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 H4A 120.9 . . ?
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
Cl1 C3 1.750(4) . ?
N4 N3 1.340(4) . ?
N4 C8 1.323(4) . ?
N4 H4 0.84(4) . ?
N1 N2 1.365(4) . ?
N1 C8 1.323(4) . ?
N3 N2 1.283(4) . ?
C8 C7 1.484(5) . ?
C1 C2 1.382(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.509(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.384(5) . ?
C3 C4 1.359(5) . ?
C4 H4A 0.9300 . ?
