#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:07:53 +0300 (Fri, 05 May 2023) $
#$Revision: 283030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/10/7131055.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_7131055
loop_
_publ_author_name
'Biswal, Pragati'
'Nanda, Tanmayee'
'Banjare, Shyam Kumar'
'Mohanty, Smruti Ranjan'
'Mishra, Ranjit'
'Ravikumar, Ponneri C.'
_publ_section_title
;
 N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed
 stereoselective trans-propenylation of aryl C(sp²)-H
 bond.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              199
_journal_page_last               202
_journal_paper_doi               10.1039/d2cc06048e
_journal_volume                  59
_journal_year                    2022
_chemical_formula_moiety         'C18 H19 Cl N4'
_chemical_formula_sum            'C18 H19 Cl N4'
_chemical_formula_weight         326.83
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2021-04-13 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                65.854(3)
_cell_angle_beta                 83.509(3)
_cell_angle_gamma                69.754(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4208(3)
_cell_length_b                   10.0653(3)
_cell_length_c                   10.3448(3)
_cell_measurement_reflns_used    6700
_cell_measurement_temperature    299.7(5)
_cell_measurement_theta_max      74.6430
_cell_measurement_theta_min      4.6830
_cell_volume                     839.33(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.8(5)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9580
_diffrn_measured_fraction_theta_max 0.9563
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -19.00   0.50    0.77    --  -38.50 -72.00 -73.00  166
  2  ω     30.00 113.00   0.50    0.77    --   49.56  72.00  56.00  166
  3  ω    -14.00  69.00   0.50    0.77    --   49.56 -72.00 -73.00  166
  4  ω     84.00 166.00   0.50    9.28    --  102.63  72.00  56.00  164
  5  ω     39.00 122.00   0.50    9.28    --  102.63 -72.00 -73.00  166
  6  ω    -44.00 -13.50   0.50    0.77    --  -38.50  19.00  30.00   61
  7  ω    -58.00  25.00   0.50    0.77    --  -38.50  72.00  56.00  166
  8  ω      7.00  86.00   0.50    0.77    --   49.56 -99.00 150.00  158
  9  ω     92.00 166.00   0.50    9.28    --  102.63  56.00  42.85  148
 10  ω     34.00 107.00   0.50    9.28    --  102.63 -94.00-120.00  146
 11  ω     97.00 168.00   0.50    9.28    --  102.63 125.00 -30.00  142
 12  ω     98.00 167.00   0.50    9.28    --  102.63  45.00  60.00  138
 13  ω     35.00 106.00   0.50    9.28    --  102.63 -30.00  30.00  142
 14  ω     35.00 106.00   0.50    9.28    --  102.63 -30.00-120.00  142
 15  ω     34.00 107.00   0.50    9.28    --  102.63 -94.00  30.00  146
 16  ω     38.00 112.00   0.50    9.28    --  102.63-125.00-120.00  148
 17  ω     34.00 107.00   0.50    9.28    --  102.63 -94.00  90.00  146
 18  ω     35.00 106.00   0.50    9.28    --  102.63 -30.00  90.00  142
 19  ω    103.00 167.00   0.50    9.28    --  102.63  77.00 150.00  128
 20  ω     38.00 126.00   0.50    9.28    --  102.63 -77.00-120.00  176
 21  ω     40.00 116.00   0.50    9.28    --  102.63 -61.00   0.00  152
 22  ω     98.00 167.00   0.50    9.28    --  102.63  45.00 -60.00  138
 23  ω     34.00 111.00   0.50    9.28    --  102.63 -15.00-120.00  154
 24  ω     34.00 107.00   0.50    9.28    --  102.63 -94.00 120.00  146
 25  ω    103.00 167.00   0.50    9.28    --  102.63  77.00-120.00  128
 26  ω    103.00 167.00   0.50    9.28    --  102.63  77.00 -30.00  128
 27  ω     34.00 107.00   0.50    9.28    --  102.63 -94.00 -60.00  146
 28  ω     38.00 107.00   0.50    9.28    --  102.63 -45.00  60.00  138
 29  ω     38.00 107.00   0.50    0.77    --   49.56  57.00 150.00  138
 30  ω     38.00 113.00   0.50    0.77    --   49.56  57.00-150.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11437
_diffrn_reflns_theta_full        75.5422
_diffrn_reflns_theta_max         75.54
_diffrn_reflns_theta_min         4.69
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.2931
_exptl_crystal_description       cube
_exptl_crystal_F_000             345.6211
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.1538
_refine_diff_density_min         -0.2920
_refine_diff_density_rms         0.0466
_refine_ls_d_res_high            0.7961
_refine_ls_d_res_low             9.4345
_refine_ls_goodness_of_fit_ref   1.0307
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0307
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.0016
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0759P)²+0.1830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2838
_reflns_number_total             3328
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2cc06048e2.cif
_cod_data_source_block           pbtn-purine
_cod_depositor_comments
'Adding full bibliography for 7131054--7131055.cif.'
_cod_database_code               7131055
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C38(H38a,H38b)
2.c Aromatic/amide H refined with riding coordinates:
 C29(H29), C26(H26), C30(H30), C36(H36), C24(H24), C31(H31), C37(H37)
2.d Idealised Me refined as rotating group:
 C40(H40a,H40b,H40c), C32(H32a,H32b,H32c), C41(H41a,H41b,H41c)
;
_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
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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_refinement_flags_posn
Cl16 Cl 0.13968(8) 0.79356(8) 0.98814(7) 0.0920(3) Uani 1.000000 .
N18 N 0.57845(18) 1.42319(18) 0.36904(15) 0.0552(4) Uani 1.000000 .
N19 N 0.37781(17) 1.31662(18) 0.46102(16) 0.0554(4) Uani 1.000000 .
C34 C 0.60091(19) 1.21337(19) 0.60098(17) 0.0480(4) Uani 1.000000 .
N17 N 0.79636(17) 1.29723(19) 0.53107(16) 0.0551(4) Uani 1.000000 .
C35 C 0.65333(19) 1.32056(19) 0.48970(17) 0.0478(4) Uani 1.000000 .
C28 C 0.37878(18) 1.11222(19) 0.68940(18) 0.0496(4) Uani 1.000000 .
C29 C 0.3375(2) 1.0147(2) 0.6480(2) 0.0608(5) Uani 1.000000 .
H29 H 0.3594(2) 1.0162(2) 0.5576(2) 0.0730(6) Uiso 1.000000 R
C27 C 0.34357(19) 1.11405(19) 0.82433(18) 0.0494(4) Uani 1.000000 .
N16 N 0.70981(18) 1.1258(2) 0.70963(17) 0.0620(4) Uani 1.000000 .
C26 C 0.2685(2) 1.0138(2) 0.9152(2) 0.0570(4) Uani 1.000000 .
H26 H 0.2438(2) 1.0123(2) 1.0053(2) 0.0684(5) Uiso 1.000000 R
C30 C 0.3779(2) 1.2216(2) 0.86769(19) 0.0548(4) Uani 1.000000 .
H30 H 0.4233(2) 1.2883(2) 0.80068(19) 0.0658(5) Uiso 1.000000 R
C25 C 0.2315(2) 0.9179(2) 0.8714(2) 0.0615(5) Uani 1.000000 .
C33 C 0.45488(19) 1.21627(19) 0.58355(17) 0.0476(4) Uani 1.000000 .
C38 C 0.8944(2) 1.3881(3) 0.4529(2) 0.0625(5) Uani 1.000000 .
H38a H 0.8407(2) 1.4957(3) 0.4347(2) 0.0750(6) Uiso 1.000000 R
H38b H 0.9835(2) 1.3547(3) 0.5117(2) 0.0750(6) Uiso 1.000000 R
C36 C 0.4425(2) 1.4125(2) 0.36344(19) 0.0583(4) Uani 1.000000 .
H36 H 0.3849(2) 1.4806(2) 0.28072(19) 0.0700(5) Uiso 1.000000 R
C39 C 0.9442(2) 1.3740(2) 0.3130(2) 0.0605(5) Uani 1.000000 .
H39 H 0.8543(2) 1.3964(2) 0.2584(2) 0.0726(6) Uiso 1.000000 R
C24 C 0.2647(3) 0.9162(3) 0.7388(3) 0.0688(5) Uani 1.000000 .
H24 H 0.2387(3) 0.8502(3) 0.7113(3) 0.0825(6) Uiso 1.000000 R
C40 C 1.0205(3) 1.4945(3) 0.2308(3) 0.0865(7) Uani 1.000000 .
H40a H 0.9525(10) 1.5950(5) 0.220(2) 0.1297(11) Uiso 1.000000 GR
H40b H 1.1108(14) 1.4718(16) 0.2818(12) 0.1297(11) Uiso 1.000000 GR
H40c H 1.046(2) 1.4924(18) 0.1391(10) 0.1297(11) Uiso 1.000000 GR
C32 C 0.3871(3) 1.3493(3) 1.0250(3) 0.0781(6) Uani 1.000000 .
H32a H 0.444(2) 1.4013(17) 0.9508(11) 0.1171(9) Uiso 1.000000 GR
H32b H 0.2943(3) 1.4233(14) 1.035(2) 0.1171(9) Uiso 1.000000 GR
H32c H 0.446(2) 1.2971(4) 1.1125(12) 0.1171(9) Uiso 1.000000 GR
C31 C 0.3523(2) 1.2347(3) 0.9887(2) 0.0646(5) Uani 1.000000 .
H31 H 0.3091(2) 1.1675(3) 1.0580(2) 0.0775(6) Uiso 1.000000 R
C41 C 1.0489(3) 1.2146(3) 0.3347(3) 0.0840(7) Uani 1.000000 .
H41a H 1.1420(10) 1.1951(10) 0.380(2) 0.1260(10) Uiso 1.000000 GR
H41b H 1.0022(10) 1.1402(4) 0.3937(19) 0.1260(10) Uiso 1.000000 GR
H41c H 1.069(2) 1.2067(8) 0.2446(4) 0.1260(10) Uiso 1.000000 GR
C37 C 0.8212(2) 1.1804(3) 0.6626(2) 0.0640(5) Uani 1.000000 .
H37 H 0.9110(2) 1.1425(3) 0.7150(2) 0.0768(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C36 N18 C35 111.53(15) . . ?
C36 N19 C33 118.54(16) . . ?
N16 C34 C35 110.10(15) . . ?
C33 C34 C35 116.56(16) . . ?
C33 C34 N16 133.34(16) . . ?
C38 N17 C35 126.37(16) . . ?
C37 N17 C35 105.14(14) . . ?
C37 N17 C38 128.34(17) . . ?
C34 C35 N18 126.36(16) . . ?
N17 C35 N18 127.60(15) . . ?
N17 C35 C34 106.04(15) . . ?
C27 C28 C29 120.22(15) . . ?
C33 C28 C29 117.35(15) . . ?
C33 C28 C27 122.38(15) . . ?
H29 C29 C28 119.44(11) . . ?
C24 C29 C28 121.13(18) . . ?
C24 C29 H29 119.44(12) . . ?
C26 C27 C28 117.94(16) . . ?
C30 C27 C28 121.39(15) . . ?
C30 C27 C26 120.61(16) . . ?
C37 N16 C34 103.60(15) . . ?
H26 C26 C27 119.92(11) . . ?
C25 C26 C27 120.15(17) . . ?
C25 C26 H26 119.92(11) . . ?
H30 C30 C27 116.18(9) . . ?
C31 C30 C27 127.64(17) . . ?
C31 C30 H30 116.18(12) . . ?
C26 C25 Cl16 118.78(16) . . ?
C24 C25 Cl16 118.95(15) . . ?
C24 C25 C26 122.27(17) . . ?
C34 C33 N19 118.34(15) . . ?
C28 C33 N19 116.88(15) . . ?
C28 C33 C34 124.75(16) . . ?
H38a C38 N17 108.86(10) . . ?
H38b C38 N17 108.86(11) . . ?
H38b C38 H38a 107.7 . . ?
C39 C38 N17 113.52(15) . . ?
C39 C38 H38a 108.86(11) . . ?
C39 C38 H38b 108.86(11) . . ?
N19 C36 N18 128.64(18) . . ?
H36 C36 N18 115.68(10) . . ?
H36 C36 N19 115.68(11) . . ?
H39 C39 C38 108.61(11) . . ?
C40 C39 C38 108.25(18) . . ?
C40 C39 H39 108.61(13) . . ?
C41 C39 C38 111.74(19) . . ?
C41 C39 H39 108.61(13) . . ?
C41 C39 C40 110.94(19) . . ?
C25 C24 C29 118.27(18) . . ?
H24 C24 C29 120.87(12) . . ?
H24 C24 C25 120.87(11) . . ?
H40a C40 C39 109.5 . . ?
H40b C40 C39 109.5 . . ?
H40b C40 H40a 109.5 . . ?
H40c C40 C39 109.5 . . ?
H40c C40 H40a 109.5 . . ?
H40c C40 H40b 109.5 . . ?
H32b C32 H32a 109.5 . . ?
H32c C32 H32a 109.5 . . ?
H32c C32 H32b 109.5 . . ?
C31 C32 H32a 109.5 . . ?
C31 C32 H32b 109.5 . . ?
C31 C32 H32c 109.5 . . ?
C32 C31 C30 124.9(2) . . ?
H31 C31 C30 117.54(12) . . ?
H31 C31 C32 117.54(13) . . ?
H41a C41 C39 109.5 . . ?
H41b C41 C39 109.5 . . ?
H41b C41 H41a 109.5 . . ?
H41c C41 C39 109.5 . . ?
H41c C41 H41a 109.5 . . ?
H41c C41 H41b 109.5 . . ?
N16 C37 N17 115.12(17) . . ?
H37 C37 N17 122.44(10) . . ?
H37 C37 N16 122.44(11) . . ?
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
Cl16 C25 1.7467(18) . ?
N18 C35 1.328(2) . ?
N18 C36 1.331(2) . ?
N19 C33 1.344(2) . ?
N19 C36 1.339(2) . ?
C34 C35 1.399(2) . ?
C34 N16 1.385(2) . ?
C34 C33 1.396(2) . ?
N17 C35 1.372(2) . ?
N17 C38 1.468(2) . ?
N17 C37 1.364(3) . ?
C28 C29 1.394(2) . ?
C28 C27 1.404(2) . ?
C28 C33 1.488(2) . ?
C29 H29 0.9300 . ?
C29 C24 1.378(3) . ?
C27 C26 1.403(2) . ?
C27 C30 1.466(2) . ?
N16 C37 1.306(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.373(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.299(3) . ?
C25 C24 1.377(3) . ?
C38 H38a 0.9700 . ?
C38 H38b 0.9700 . ?
C38 C39 1.517(3) . ?
C36 H36 0.9300 . ?
C39 H39 0.9800 . ?
C39 C40 1.527(3) . ?
C39 C41 1.502(3) . ?
C24 H24 0.9300 . ?
C40 H40a 0.9600 . ?
C40 H40b 0.9600 . ?
C40 H40c 0.9600 . ?
C32 H32a 0.9600 . ?
C32 H32b 0.9600 . ?
C32 H32c 0.9600 . ?
C32 C31 1.491(3) . ?
C31 H31 0.9300 . ?
C41 H41a 0.9600 . ?
C41 H41b 0.9600 . ?
C41 H41c 0.9600 . ?
C37 H37 0.9300 . ?
