#------------------------------------------------------------------------------
#$Date: 2023-10-10 00:56:30 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132185.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_7132185
loop_
_publ_author_name
'Ahsan, Mollah Rohan'
'Singh, Lavanya'
'Varma, Harshit'
'Mukherjee, Arijit'
_publ_section_title
;
 Exploiting benzilic acid as a modular template: controlling
 photoreactivity and solid to liquid transition during photodimerization.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04257j
_journal_year                    2023
_chemical_formula_moiety         'C13 H9 Cl2 N'
_chemical_formula_sum            'C13 H9 Cl2 N'
_chemical_formula_weight         250.11
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-08-23 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 89.998(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.87140(10)
_cell_length_b                   11.4217(3)
_cell_length_c                   26.3704(6)
_cell_measurement_reflns_used    4694
_cell_measurement_temperature    295
_cell_measurement_theta_max      78.2020
_cell_measurement_theta_min      4.2300
_cell_volume                     1166.05(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  21.00   0.50    2.00    --    0.00  57.00 150.00   64
  2  ω      9.00  36.00   0.50    2.00    --    0.00  77.00-150.00   54
  3  ω    -23.00  88.00   0.50    2.00    --    0.00  57.00 -60.00  222
  4  ω    -88.00  -9.00   0.50    2.00    --    0.00 -19.00-180.00  158
  5  ω    -18.00  34.00   0.50    2.00    --    0.00  82.00 150.00  104
  6  ω     24.00  50.00   0.50   24.00    --  107.20 -82.00-120.00   52
  7  ω     51.00 128.00   0.50   24.00    --  107.20 -82.00 -60.00  154
  8  ω     89.00 194.00   0.50   24.00    --  107.20  15.00 120.00  210
  9  ω     26.00 136.00   0.50   24.00    --  107.20 -82.00-180.00  220
 10  ω     95.00 174.00   0.50   24.00    --  107.20  15.00  30.00  158
 11  ω     20.00 129.00   0.50   24.00    --  107.20 -61.00  30.00  218
 12  ω     18.00  83.00   0.50   24.00    --  107.20 -30.00-150.00  130
 13  ω    170.00 197.00   0.50   24.00    --  107.20  15.00 -60.00   54
 14  ω     96.00 122.00   0.50   24.00    --  107.20  77.00  90.00   52
 15  ω    147.00 197.00   0.50   24.00    --  107.20  77.00  90.00  100
 16  ω     73.00  98.00   0.50   24.00    --  107.20 -82.00-120.00   50
 17  ω     64.00 108.00   0.50   24.00    --  107.20 -30.00 -60.00   88
 18  ω     22.00 102.00   0.50   24.00    --  107.20 -61.00-180.00  160
 19  ω     75.00 123.00   0.50   24.00    --  107.20 -82.00  30.00   96
 20  ω     44.00  70.00   0.50   24.00    --  107.20 -82.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0790075000
_diffrn_orient_matrix_UB_12      -0.1074527000
_diffrn_orient_matrix_UB_13      0.0333984000
_diffrn_orient_matrix_UB_21      -0.0173810000
_diffrn_orient_matrix_UB_22      0.0776020000
_diffrn_orient_matrix_UB_23      0.0477125000
_diffrn_orient_matrix_UB_31      -0.3895190000
_diffrn_orient_matrix_UB_32      -0.0251403000
_diffrn_orient_matrix_UB_33      0.0046222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            10123
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.367
_diffrn_reflns_theta_min         3.870
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0453
_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)+(0.0725P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2141
_reflns_number_total             2483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           dcl_4
_cod_database_code               7132185
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C24HN2Cl2
_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   0.648
_shelx_estimated_absorpt_t_min   0.451
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.529(2)
 0.471(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C9(H9), C7(H7), C11(H11), C5(H5), C2(H2), C3(H3), C13(H13)
;
_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 2.825
_oxdiff_exptl_absorpt_empirical_full_min 0.428
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2360(11) 1.2877(3) 0.71211(15) 0.0909(10) Uani 1 1 d . . . . .
H1 H 0.201153 1.367457 0.707126 0.109 Uiso 1 1 calc R U . . .
Cl1 Cl -0.4269(3) 0.82371(8) 0.46124(3) 0.0914(3) Uani 1 1 d . . . . .
Cl2 Cl -0.1825(5) 0.47287(7) 0.59060(5) 0.1366(6) Uani 1 1 d . . . . .
C6 C 0.0459(8) 1.0133(2) 0.64132(10) 0.0664(6) Uani 1 1 d . . . . .
H6 H -0.062724 1.046712 0.613387 0.080 Uiso 1 1 calc R U . . .
C8 C -0.0527(8) 0.8188(2) 0.60248(9) 0.0622(6) Uani 1 1 d . . . . .
C9 C -0.0543(9) 0.6994(2) 0.61283(11) 0.0713(7) Uani 1 1 d . . . . .
H9 H 0.025438 0.671994 0.643911 0.086 Uiso 1 1 calc R U . . .
C7 C 0.0758(8) 0.8980(2) 0.64185(9) 0.0656(6) Uani 1 1 d . . . . .
H7 H 0.187552 0.864461 0.669487 0.079 Uiso 1 1 calc R U . . .
N1 N 0.3872(8) 1.2545(3) 0.75507(11) 0.0902(8) Uani 1 1 d . . . . .
C11 C -0.2908(9) 0.6578(2) 0.53020(11) 0.0739(7) Uani 1 1 d . . . . .
H11 H -0.369786 0.604536 0.506184 0.089 Uiso 1 1 calc R U . . .
C5 C 0.1271(9) 1.2125(2) 0.67442(12) 0.0764(8) Uani 1 1 d . . . . .
H5 H 0.026638 1.241600 0.644968 0.092 Uiso 1 1 calc R U . . .
C10 C -0.1749(10) 0.6214(2) 0.57673(12) 0.0778(9) Uani 1 1 d . . . . .
C2 C 0.4220(10) 1.1390(3) 0.76082(12) 0.0858(9) Uani 1 1 d . . . . .
H2 H 0.520260 1.112249 0.790841 0.103 Uiso 1 1 calc R U . . .
C3 C 0.3243(8) 1.0575(3) 0.72598(10) 0.0724(7) Uani 1 1 d . . . . .
H3 H 0.361207 0.978338 0.732242 0.087 Uiso 1 1 calc R U . . .
C13 C -0.1687(8) 0.8562(2) 0.55490(10) 0.0662(6) Uani 1 1 d . . . . .
H13 H -0.166167 0.935458 0.546762 0.079 Uiso 1 1 calc R U . . .
C4 C 0.1693(7) 1.0931(2) 0.68103(9) 0.0641(6) Uani 1 1 d . . . . .
C12 C -0.2858(8) 0.7760(2) 0.52037(10) 0.0659(6) 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 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 -2 0.0180
0 7 -2 0.0180
0 7 2 0.0180
0 -7 2 0.0180
0 -7 -2 0.0180
0 7 -2 0.0180
0 7 -2 0.0180
0 -7 -2 0.0180
0 7 2 0.0180
0 -7 2 0.0180
0 -7 2 0.0180
0 7 2 0.0180
0 0 1 0.0000
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
N1 C1 H1 117.6 . . ?
N1 C1 C5 124.8(3) . . ?
C5 C1 H1 117.6 . . ?
C7 C6 H6 117.2 . . ?
C7 C6 C4 125.6(2) . . ?
C4 C6 H6 117.2 . . ?
C9 C8 C7 117.9(2) . . ?
C9 C8 C13 118.3(2) . . ?
C13 C8 C7 123.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C6 C7 C8 125.3(2) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C1 N1 C2 115.0(3) . . ?
C10 C11 H11 121.3 . . ?
C10 C11 C12 117.5(2) . . ?
C12 C11 H11 121.3 . . ?
C1 C5 H5 120.4 . . ?
C1 C5 C4 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C9 C10 Cl2 119.3(2) . . ?
C11 C10 Cl2 118.6(2) . . ?
C11 C10 C9 122.1(3) . . ?
N1 C2 H2 117.6 . . ?
N1 C2 C3 124.8(3) . . ?
C3 C2 H2 117.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C5 C4 C6 118.9(2) . . ?
C5 C4 C3 116.6(2) . . ?
C3 C4 C6 124.5(2) . . ?
C11 C12 Cl1 118.17(19) . . ?
C13 C12 Cl1 119.4(2) . . ?
C13 C12 C11 122.4(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
C1 H1 0.9300 . ?
C1 N1 1.330(5) . ?
C1 C5 1.380(4) . ?
Cl1 C12 1.740(3) . ?
Cl2 C10 1.736(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.322(4) . ?
C6 C4 1.469(3) . ?
C8 C9 1.391(3) . ?
C8 C7 1.464(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C7 H7 0.9300 . ?
N1 C2 1.334(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.371(4) . ?
C11 C12 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.369(4) . ?
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
C1 N1 C2 C3 1.9(6) . . . . ?
C1 C5 C4 C6 178.6(3) . . . . ?
C1 C5 C4 C3 -0.5(5) . . . . ?
C8 C9 C10 Cl2 -178.9(3) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8 C13 C12 Cl1 -179.6(2) . . . . ?
C8 C13 C12 C11 -0.9(5) . . . . ?
C9 C8 C7 C6 -169.0(3) . . . . ?
C9 C8 C13 C12 1.2(5) . . . . ?
C7 C6 C4 C5 178.3(3) . . . . ?
C7 C6 C4 C3 -2.6(5) . . . . ?
C7 C8 C9 C10 179.8(3) . . . . ?
C7 C8 C13 C12 -179.8(3) . . . . ?
N1 C1 C5 C4 1.2(6) . . . . ?
N1 C2 C3 C4 -1.4(6) . . . . ?
C5 C1 N1 C2 -1.8(6) . . . . ?
C10 C11 C12 Cl1 179.2(3) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C2 C3 C4 C6 -178.4(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C13 C8 C9 C10 -1.2(6) . . . . ?
C13 C8 C7 C6 12.0(5) . . . . ?
C4 C6 C7 C8 179.0(3) . . . . ?
C12 C11 C10 Cl2 179.3(3) . . . . ?
C12 C11 C10 C9 -0.4(6) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.529(2)
2 0.471(2)
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4434 -7.2387 -2.0914 0.7430 -0.6692 -0.0004
0.4465 7.2395 -2.0854 -0.8123 0.4545 -0.3656
-0.4434 7.2387 2.0914 -0.7430 0.6692 0.0004
-0.4465 -7.2395 2.0854 0.8123 -0.4545 0.3656
0.4434 -7.2387 -2.0914 0.7430 -0.6692 -0.0004
-0.4440 7.2388 -2.0836 -0.8825 0.4701 -0.0187
0.4465 7.2395 -2.0854 -0.8123 0.4545 -0.3656
-0.4470 -7.2394 -2.0895 0.6728 -0.6537 0.3465
-0.4434 7.2387 2.0914 -0.7430 0.6692 0.0004
0.4440 -7.2388 2.0836 0.8825 -0.4701 0.0187
-0.4465 -7.2395 2.0854 0.8123 -0.4545 0.3656
0.4470 7.2394 2.0895 -0.6728 0.6537 -0.3465
0.0001 -0.0000 0.9997 0.0334 0.0477 0.0046
