#------------------------------------------------------------------------------
#$Date: 2026-03-21 02:51:48 +0100 (Sat 21 de Mar de 2026) $
#$Revision: 305160 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/10/7161084.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_7161084
loop_
_publ_author_name
'Wang, Yan-Bo'
'Cui, Yan-Zhao'
'Li, He'
'Liu, Huiyi'
'Yuan, Hao-Qi'
'Zhou, Hao-Tian'
'Wang, Xiao-Sai'
_publ_section_title
;
 Pyridine-boryl radicals-mediated reductive homocoupling of para-quinone
 methides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D6OB00078A
_journal_year                    2025
_chemical_formula_moiety         'C21 H25 Cl2 O'
_chemical_formula_sum            'C21 H25 Cl2 O'
_chemical_formula_weight         364.31
_chemical_name_systematic        CYZ-285
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2026-01-13 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 132.633(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.434(5)
_cell_length_b                   15.147(3)
_cell_length_c                   18.526(5)
_cell_measurement_reflns_used    3571
_cell_measurement_temperature    294
_cell_measurement_theta_max      25.997
_cell_measurement_theta_min      2.243
_cell_volume                     4631.5(19)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1081
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.825
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.1594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.045
_exptl_crystal_description       block
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0877
_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)+(0.1332P)²+2.4491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2406
_refine_ls_wR_factor_ref         0.2672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ob00078a2.cif
_cod_data_source_block           m15455_0m_sq
_cod_original_cell_volume        4631.6(19)
_cod_database_code               7161084
_shelx_shelxl_version_number     2018/3
_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   0.967
_shelx_estimated_absorpt_t_min   0.951
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H003-H00K
 2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C00I(H00I)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G)
3.c Idealised Me refined as rotating group:
 C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q), C00N(H00R,H00S,H00T), C00O(H00U,
 H00V,H00W)
3.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl01 Cl 0.40046(8) 0.30402(8) 0.51760(10) 0.0723(5) Uani 1 1 d . . . . .
Cl02 Cl 0.39970(9) 0.23018(9) 0.80647(11) 0.0839(5) Uani 1 1 d . . . . .
O003 O 0.2978(2) 0.67486(18) 0.5753(2) 0.0595(9) Uani 1 1 d . . . . .
H003 H 0.252647 0.669787 0.520316 0.089 Uiso 1 1 calc DGR . . . .
C004 C 0.3843(2) 0.5668(2) 0.5905(3) 0.0420(9) Uani 1 1 d . . . . .
C005 C 0.3354(3) 0.5925(2) 0.6085(3) 0.0481(10) Uani 1 1 d . . . . .
C006 C 0.4215(2) 0.4846(2) 0.6274(3) 0.0451(10) Uani 1 1 d . . . . .
H006 H 0.453943 0.464708 0.616291 0.054 Uiso 1 1 calc R . . . .
C007 C 0.4040(2) 0.2646(2) 0.6647(3) 0.0496(11) Uani 1 1 d . . . . .
C008 C 0.4122(2) 0.4313(2) 0.6798(3) 0.0473(11) Uani 1 1 d . . . . .
C009 C 0.3239(2) 0.5415(3) 0.6605(3) 0.0470(10) Uani 1 1 d . . . . .
C00A C 0.3990(3) 0.6250(3) 0.5358(3) 0.0524(11) Uani 1 1 d . . . . .
C00B C 0.3758(2) 0.2420(3) 0.5731(3) 0.0525(12) Uani 1 1 d . . . . .
C00C C 0.3639(2) 0.4604(3) 0.6951(3) 0.0516(11) Uani 1 1 d . . . . .
H00C H 0.357436 0.424553 0.730164 0.062 Uiso 1 1 calc R . . . .
C00D C 0.3743(3) 0.2117(3) 0.6951(3) 0.0552(12) Uani 1 1 d . . . . .
C00E C 0.2965(3) 0.1215(3) 0.5515(4) 0.0652(14) Uani 1 1 d . . . . .
H00E H 0.261213 0.074560 0.514675 0.078 Uiso 1 1 calc R . . . .
C00F C 0.3235(3) 0.1713(3) 0.5168(4) 0.0608(13) Uani 1 1 d . . . . .
H00F H 0.307297 0.158182 0.456648 0.073 Uiso 1 1 calc R . . . .
C00G C 0.3216(3) 0.1411(3) 0.6402(4) 0.0649(14) Uani 1 1 d . . . . .
H00G H 0.303580 0.107405 0.664236 0.078 Uiso 1 1 calc R . . . .
C00H C 0.2710(3) 0.5715(3) 0.6801(4) 0.0597(12) Uani 1 1 d . . . . .
C00I C 0.4583(2) 0.3448(2) 0.7293(4) 0.0622(14) Uani 1 1 d . . . . .
H00I H 0.464257 0.340642 0.786701 0.075 Uiso 1 1 calc R . . . .
C00J C 0.3183(4) 0.6452(4) 0.4313(4) 0.0680(14) Uani 1 1 d . . . . .
H00A H 0.287(4) 0.592(4) 0.394(5) 0.102 Uiso 1 1 d R . . . .
H00B H 0.328(4) 0.667(4) 0.397(5) 0.102 Uiso 1 1 d R . . . .
C00K C 0.1833(3) 0.5864(5) 0.5835(5) 0.0757(16) Uani 1 1 d . . . . .
H00H H 0.154(4) 0.602(4) 0.600(5) 0.114 Uiso 1 1 d R . . . .
H00J H 0.162(4) 0.531(5) 0.548(5) 0.114 Uiso 1 1 d R . . . .
C00L C 0.4526(3) 0.5780(3) 0.5243(4) 0.0676(14) Uani 1 1 d . . . . .
H00L H 0.504376 0.565307 0.587976 0.101 Uiso 1 1 calc GR . . . .
H00M H 0.459800 0.615357 0.488896 0.101 Uiso 1 1 calc GR . . . .
H00N H 0.427151 0.523849 0.488888 0.101 Uiso 1 1 calc GR . . . .
C00M C 0.3048(3) 0.6582(4) 0.7412(4) 0.0728(14) Uani 1 1 d . . . . .
H00O H 0.357444 0.647298 0.804509 0.109 Uiso 1 1 calc GR . . . .
H00P H 0.268901 0.678243 0.749140 0.109 Uiso 1 1 calc GR . . . .
H00Q H 0.308816 0.702619 0.707725 0.109 Uiso 1 1 calc GR . . . .
C00N C 0.4449(3) 0.7101(3) 0.5952(4) 0.0720(15) Uani 1 1 d . . . . .
H00R H 0.412938 0.743109 0.602780 0.108 Uiso 1 1 calc GR . . . .
H00S H 0.454626 0.745353 0.560961 0.108 Uiso 1 1 calc GR . . . .
H00T H 0.495756 0.694610 0.658699 0.108 Uiso 1 1 calc GR . . . .
C00O C 0.2687(4) 0.5036(4) 0.7396(5) 0.0876(18) Uani 1 1 d . . . . .
H00U H 0.240879 0.451542 0.700695 0.131 Uiso 1 1 calc GR . . . .
H00V H 0.240800 0.528324 0.757371 0.131 Uiso 1 1 calc GR . . . .
H00W H 0.323071 0.488501 0.797864 0.131 Uiso 1 1 calc GR . . . .
H00D H 0.282(3) 0.683(3) 0.432(3) 0.066(14) Uiso 1 1 d . . . . .
H00K H 0.181(3) 0.621(3) 0.539(4) 0.069(16) Uiso 1 1 d 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'
O O 0.0106 0.0060 '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
C005 O003 H003 109.5 . . ?
C005 C004 C00A 123.4(3) . . ?
C006 C004 C005 116.0(4) . . ?
C006 C004 C00A 120.6(4) . . ?
O003 C005 C004 118.8(4) . . ?
C009 C005 O003 117.6(4) . . ?
C009 C005 C004 123.6(3) . . ?
C004 C006 H006 118.7 . . ?
C008 C006 C004 122.6(4) . . ?
C008 C006 H006 118.7 . . ?
C00B C007 C00I 127.0(4) . . ?
C00D C007 C00B 114.1(4) . . ?
C00D C007 C00I 118.8(4) . . ?
C006 C008 C00I 123.9(4) . . ?
C00C C008 C006 118.5(3) . . ?
C00C C008 C00I 117.4(4) . . ?
C005 C009 C00C 116.5(4) . . ?
C005 C009 C00H 122.5(4) . . ?
C00C C009 C00H 121.0(4) . . ?
C004 C00A C00J 110.3(4) . . ?
C004 C00A C00N 110.2(4) . . ?
C00J C00A C00N 112.2(4) . . ?
C00L C00A C004 111.4(3) . . ?
C00L C00A C00J 106.4(4) . . ?
C00L C00A C00N 106.1(4) . . ?
C007 C00B Cl01 121.6(3) . . ?
C007 C00B C00F 123.7(4) . . ?
C00F C00B Cl01 114.6(4) . . ?
C008 C00C C009 122.8(4) . . ?
C008 C00C H00C 118.6 . . ?
C009 C00C H00C 118.6 . . ?
C007 C00D Cl02 121.7(3) . . ?
C007 C00D C00G 123.5(5) . . ?
C00G C00D Cl02 114.8(4) . . ?
C00F C00E H00E 120.2 . . ?
C00G C00E H00E 120.2 . . ?
C00G C00E C00F 119.6(4) . . ?
C00B C00F H00F 120.4 . . ?
C00E C00F C00B 119.1(5) . . ?
C00E C00F H00F 120.4 . . ?
C00D C00G H00G 120.0 . . ?
C00E C00G C00D 120.0(5) . . ?
C00E C00G H00G 120.0 . . ?
C009 C00H C00K 110.9(4) . . ?
C009 C00H C00M 110.6(4) . . ?
C009 C00H C00O 112.4(4) . . ?
C00K C00H C00M 109.4(4) . . ?
C00O C00H C00K 107.2(5) . . ?
C00O C00H C00M 106.2(4) . . ?
C007 C00I H00I 104.2 . . ?
C008 C00I C007 110.4(3) . . ?
C008 C00I H00I 104.2 . . ?
C00I C00I C007 117.4(4) 2_656 . ?
C00I C00I C008 114.8(3) 2_656 . ?
C00I C00I H00I 104.2 2_656 . ?
C00A C00J H00A 113(4) . . ?
C00A C00J H00B 110(4) . . ?
C00A C00J H00D 112(3) . . ?
H00A C00J H00B 103(5) . . ?
H00A C00J H00D 106(5) . . ?
H00B C00J H00D 113(5) . . ?
C00H C00K H00H 107(4) . . ?
C00H C00K H00J 109(4) . . ?
C00H C00K H00K 111(3) . . ?
H00H C00K H00J 107(5) . . ?
H00H C00K H00K 121(5) . . ?
H00J C00K H00K 101(5) . . ?
C00A C00L H00L 109.5 . . ?
C00A C00L H00M 109.5 . . ?
C00A C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
C00H C00M H00O 109.5 . . ?
C00H C00M H00P 109.5 . . ?
C00H C00M H00Q 109.5 . . ?
H00O C00M H00P 109.5 . . ?
H00O C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?
C00A C00N H00R 109.5 . . ?
C00A C00N H00S 109.5 . . ?
C00A C00N H00T 109.5 . . ?
H00R C00N H00S 109.5 . . ?
H00R C00N H00T 109.5 . . ?
H00S C00N H00T 109.5 . . ?
C00H C00O H00U 109.5 . . ?
C00H C00O H00V 109.5 . . ?
C00H C00O H00W 109.5 . . ?
H00U C00O H00V 109.5 . . ?
H00U C00O H00W 109.5 . . ?
H00V C00O H00W 109.5 . . ?
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
Cl01 C00B 1.737(5) . ?
Cl02 C00D 1.752(5) . ?
O003 H003 0.8200 . ?
O003 C005 1.394(4) . ?
C004 C005 1.400(6) . ?
C004 C006 1.394(5) . ?
C004 C00A 1.538(6) . ?
C005 C009 1.388(6) . ?
C006 H006 0.9300 . ?
C006 C008 1.382(6) . ?
C007 C00B 1.394(7) . ?
C007 C00D 1.381(6) . ?
C007 C00I 1.555(5) . ?
C008 C00C 1.365(6) . ?
C008 C00I 1.532(5) . ?
C009 C00C 1.395(5) . ?
C009 C00H 1.526(6) . ?
C00A C00J 1.540(7) . ?
C00A C00L 1.531(6) . ?
C00A C00N 1.549(6) . ?
C00B C00F 1.398(6) . ?
C00C H00C 0.9300 . ?
C00D C00G 1.396(6) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.370(7) . ?
C00E C00G 1.361(7) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H C00K 1.535(7) . ?
C00H C00M 1.556(7) . ?
C00H C00O 1.534(7) . ?
C00I C00I 1.464(8) 2_656 ?
C00I H00I 0.9800 . ?
C00J H00A 0.97(6) . ?
C00J H00B 0.86(6) . ?
C00J H00D 1.00(5) . ?
C00K H00H 0.93(7) . ?
C00K H00J 0.98(7) . ?
C00K H00K 0.95(4) . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00M H00P 0.9600 . ?
C00M H00Q 0.9600 . ?
C00N H00R 0.9600 . ?
C00N H00S 0.9600 . ?
C00N H00T 0.9600 . ?
C00O H00U 0.9600 . ?
C00O H00V 0.9600 . ?
C00O H00W 0.9600 . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.020 557 115 ' '
2 0.000 0.500 0.554 557 115 ' '
