#------------------------------------------------------------------------------
#$Date: 2023-05-05 02:01:41 +0200 (Fri 05 de May de 2023) $
#$Revision: 283018 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/14/7131460.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_7131460
loop_
_publ_author_name
'Du, Jiehao'
'Cheng, Banggui'
'Jiang, Long'
'Han, Zhiji'
_publ_section_title
;
 Copper phenanthroline for selective electrochemical CO₂
 reduction on carbon paper.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4778
_journal_page_last               4781
_journal_paper_doi               10.1039/d2cc06943a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'Cl, C17 H12 N3'
_chemical_formula_sum            'C17 H12 Cl N3'
_chemical_formula_weight         293.75
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-09-20 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                98.018(11)
_cell_angle_beta                 98.510(9)
_cell_angle_gamma                96.695(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9329(7)
_cell_length_b                   10.2901(14)
_cell_length_c                   11.7596(14)
_cell_measurement_reflns_used    1881
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      73.0480
_cell_measurement_theta_min      3.8150
_cell_volume                     813.48(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      149.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -35.00   1.00    4.00    --  -41.14 -38.00 150.00   80
  2  ω   -113.00  -8.00   1.00    4.00    --  -41.14 -19.00-150.00  105
  3  ω    -92.00  -4.00   1.00    4.00    --  -41.14 125.00 -60.00   88
  4  ω     25.00  50.00   1.00    4.00    --   41.14-125.00 120.00   25
  5  ω     41.00  87.00   1.00    4.00    --   41.14-125.00-150.00   46
  6  ω     45.00 109.00   1.00   16.00    --  106.54 -94.00 -30.00   64
  7  ω     79.00 174.00   1.00   16.00    --  106.54  30.00   0.00   95
  8  ω     48.00  81.00   1.00   16.00    --  106.54 -45.00 -60.00   33
  9  ω     34.00 117.00   1.00   16.00    --  106.54-125.00-180.00   83
 10  ω     87.00 174.00   1.00   16.00    --  106.54  45.00-120.00   87
 11  ω     35.00 134.00   1.00   16.00    --  106.54 -61.00 150.00   99
 12  ω    104.00 174.00   1.00   16.00    --  106.54 125.00-180.00   70
 13  ω     79.00 109.00   1.00   16.00    --  106.54  61.00 -60.00   30
 14  ω    140.00 172.00   1.00   16.00    --  106.54  61.00 -60.00   32
 15  ω     35.00  62.00   1.00   16.00    --  106.54 -61.00   0.00   27
 16  ω     74.00 109.00   1.00   16.00    --  106.54 -94.00-120.00   35
 17  ω     90.00 130.00   1.00   16.00    --  106.54 -61.00   0.00   40
 18  ω     97.00 159.00   1.00   16.00    --  106.54  30.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1360029000
_diffrn_orient_matrix_UB_12      -0.0186911000
_diffrn_orient_matrix_UB_13      -0.0916679000
_diffrn_orient_matrix_UB_21      -0.1721026000
_diffrn_orient_matrix_UB_22      0.0081223000
_diffrn_orient_matrix_UB_23      -0.0967596000
_diffrn_orient_matrix_UB_31      0.0581190000
_diffrn_orient_matrix_UB_32      0.1513319000
_diffrn_orient_matrix_UB_33      0.0154769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4388
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        62.999
_diffrn_reflns_theta_max         62.999
_diffrn_reflns_theta_min         4.382
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.1000
_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)+(0.1879P)²+0.4580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2689
_refine_ls_wR_factor_ref         0.2833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2024
_reflns_number_total             2544
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06943a2.cif
_cod_data_source_block           exp_2203
_cod_depositor_comments
'Adding full bibliography for 7131459--7131460.cif.'
_cod_database_code               7131460
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     RED
_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   0.905
_shelx_estimated_absorpt_t_min   0.535
_reflns_odcompleteness_completeness 99.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: Cl1(0.85) Cl1A(0.15)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17)
;
_olex2_date_sample_data_collection 2021-10-01
_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 1.853
_oxdiff_exptl_absorpt_empirical_full_min 0.448
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.4561(2) 0.80869(14) 0.64944(11) 0.0615(5) Uani 0.85 1 d . . P . .
Cl1A Cl 0.3258(14) 1.0020(10) 0.4988(8) 0.072(2) Uani 0.15 1 d . . P . .
N1 N 0.7519(5) 0.5837(3) -0.1337(3) 0.0467(9) Uani 1 1 d . . . . .
N2 N 0.6753(5) 0.3145(4) -0.1857(3) 0.0521(10) Uani 1 1 d . . . . .
N3 N 0.8047(5) 0.5529(3) 0.2835(3) 0.0457(9) Uani 1 1 d . . . . .
C1 C 0.7484(5) 0.5135(4) -0.0444(4) 0.0382(9) Uani 1 1 d . . . . .
C2 C 0.7867(6) 0.7151(5) -0.1069(5) 0.0539(11) Uani 1 1 d . . . . .
H2 H 0.7901 0.7644 -0.1673 0.065 Uiso 1 1 calc R . . . .
C3 C 0.8185(6) 0.7836(4) 0.0077(4) 0.0483(11) Uani 1 1 d . . . . .
H3 H 0.8423 0.8757 0.0219 0.058 Uiso 1 1 calc R . . . .
C4 C 0.8143(5) 0.7136(4) 0.0983(4) 0.0440(10) Uani 1 1 d . . . . .
H4 H 0.8339 0.7575 0.1746 0.053 Uiso 1 1 calc R . . . .
C5 C 0.7801(5) 0.5742(4) 0.0744(4) 0.0402(9) Uani 1 1 d . . . . .
C6 C 0.7728(5) 0.4910(4) 0.1620(4) 0.0416(9) Uani 1 1 d . . . . .
C7 C 0.7378(6) 0.3575(4) 0.1373(4) 0.0456(10) Uani 1 1 d . . . . .
H7 H 0.7351 0.3071 0.1970 0.055 Uiso 1 1 calc R . . . .
C8 C 0.7048(5) 0.2937(4) 0.0183(4) 0.0450(10) Uani 1 1 d . . . . .
C9 C 0.6703(6) 0.1542(4) -0.0101(5) 0.0531(11) Uani 1 1 d . . . . .
H9 H 0.6707 0.1013 0.0478 0.064 Uiso 1 1 calc R . . . .
C10 C 0.6364(7) 0.0987(4) -0.1255(5) 0.0562(12) Uani 1 1 d . . . . .
H10 H 0.6114 0.0072 -0.1473 0.067 Uiso 1 1 calc R . . . .
C11 C 0.6398(7) 0.1806(5) -0.2088(5) 0.0578(12) Uani 1 1 d . . . . .
H11 H 0.6160 0.1409 -0.2865 0.069 Uiso 1 1 calc R . . . .
C12 C 0.7086(5) 0.3693(4) -0.0715(4) 0.0430(10) Uani 1 1 d . . . . .
C13 C 0.6473(7) 0.5620(4) 0.3373(4) 0.0538(11) Uani 1 1 d . . . . .
H13 H 0.5215 0.5277 0.2977 0.065 Uiso 1 1 calc R . . . .
C14 C 0.6742(9) 0.6226(6) 0.4514(5) 0.0686(14) Uani 1 1 d . . . . .
H14 H 0.5667 0.6290 0.4896 0.082 Uiso 1 1 calc R . . . .
C15 C 0.8622(10) 0.6741(6) 0.5092(5) 0.0753(16) Uani 1 1 d . . . . .
H15 H 0.8817 0.7164 0.5860 0.090 Uiso 1 1 calc R . . . .
C16 C 1.0207(9) 0.6619(6) 0.4516(5) 0.0743(15) Uani 1 1 d . . . . .
H16 H 1.1477 0.6952 0.4900 0.089 Uiso 1 1 calc R . . . .
C17 C 0.9904(7) 0.6008(5) 0.3378(4) 0.0546(11) Uani 1 1 d . . . . .
H17 H 1.0962 0.5924 0.2984 0.065 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 117.4(4) . . ?
C11 N2 C12 116.1(4) . . ?
C13 N3 C6 118.6(4) . . ?
C13 N3 C17 122.4(4) . . ?
C17 N3 C6 119.0(3) . . ?
N1 C1 C5 123.0(4) . . ?
N1 C1 C12 118.5(4) . . ?
C5 C1 C12 118.5(4) . . ?
N1 C2 C3 123.6(4) . . ?
C4 C3 C2 119.4(4) . . ?
C3 C4 C5 119.1(4) . . ?
C1 C5 C6 118.6(3) . . ?
C4 C5 C1 117.5(4) . . ?
C4 C5 C6 123.9(4) . . ?
C5 C6 N3 118.7(3) . . ?
C7 C6 N3 118.2(4) . . ?
C7 C6 C5 123.1(4) . . ?
C6 C7 C8 119.5(4) . . ?
C9 C8 C7 120.8(4) . . ?
C12 C8 C7 120.3(4) . . ?
C12 C8 C9 118.9(4) . . ?
C10 C9 C8 118.3(5) . . ?
C9 C10 C11 119.1(4) . . ?
N2 C11 C10 124.8(4) . . ?
N2 C12 C1 117.1(4) . . ?
N2 C12 C8 122.8(4) . . ?
C8 C12 C1 120.1(4) . . ?
N3 C13 C14 119.4(5) . . ?
C13 C14 C15 119.7(5) . . ?
C16 C15 C14 119.4(5) . . ?
C17 C16 C15 119.9(5) . . ?
N3 C17 C16 119.2(4) . . ?
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
Cl1A Cl1A 2.417(18) 2_676 ?
N1 C1 1.356(6) . ?
N1 C2 1.330(6) . ?
N2 C11 1.353(6) . ?
N2 C12 1.357(6) . ?
N3 C6 1.455(5) . ?
N3 C13 1.346(6) . ?
N3 C17 1.352(6) . ?
C1 C5 1.422(6) . ?
C1 C12 1.458(6) . ?
C2 C3 1.404(7) . ?
C3 C4 1.369(6) . ?
C4 C5 1.408(6) . ?
C5 C6 1.431(6) . ?
C6 C7 1.350(6) . ?
C7 C8 1.433(6) . ?
C8 C9 1.412(6) . ?
C8 C12 1.398(7) . ?
C9 C10 1.371(7) . ?
C10 C11 1.379(8) . ?
C13 C14 1.374(7) . ?
C14 C15 1.385(9) . ?
C15 C16 1.382(9) . ?
C16 C17 1.373(7) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.053 0.029 0.258 42.4 15.2 ?
2 0.053 -0.029 0.742 42.4 15.2 ?
