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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/43/4034336.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_4034336
loop_
_publ_author_name
'Rokade, Balaji V.'
'Guiry, Patrick J.'
_publ_section_title
;
 Enantioselective Catalytic Asymmetric A3 Coupling with
 Phosphino-Imidazoline Ligands.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5763
_journal_page_last               5772
_journal_paper_doi               10.1021/acs.joc.9b00728
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 Cl N2 O'
_chemical_formula_sum            'C19 H21 Cl N2 O'
_chemical_formula_weight         328.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.80118(4)
_cell_length_b                   13.54760(6)
_cell_length_c                   21.7017(1)
_cell_measurement_reflns_used    37755
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7620
_cell_measurement_theta_min      3.8180
_cell_volume                     1705.581(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            67785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.926
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.020
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.009(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0493P)²+0.2832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3526
_reflns_number_total             3596
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00728_si_002.cif
_cod_data_source_block           gui160
_cod_original_cell_volume        1705.582(16)
_cod_database_code               4034336
_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. 
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
N1 N 0.2354(3) 0.32151(11) 0.81881(7) 0.0214(3) Uani 1 1 d . .
C1 C 0.3987(3) 0.31598(12) 0.77824(8) 0.0203(3) Uani 1 1 d . .
Cl Cl 0.59075(8) 0.21867(3) 0.78907(2) 0.02475(12) Uani 1 1 d . .
C2 C 0.4353(3) 0.38283(12) 0.72815(8) 0.0194(3) Uani 1 1 d . .
C3 C 0.2835(3) 0.46042(12) 0.72410(8) 0.0207(3) Uani 1 1 d . .
H3 H 0.2988 0.5069 0.6916 0.025 Uiso 1 1 calc R U
C4 C 0.1046(3) 0.47195(12) 0.76785(8) 0.0198(3) Uani 1 1 d . .
C5 C -0.0565(3) 0.55090(13) 0.76654(8) 0.0228(4) Uani 1 1 d . .
H5 H -0.0447 0.6002 0.7356 0.027 Uiso 1 1 calc R U
C6 C -0.2281(4) 0.55634(14) 0.80941(9) 0.0251(4) Uani 1 1 d . .
H6 H -0.3343 0.6097 0.8083 0.030 Uiso 1 1 calc R U
C7 C -0.2489(4) 0.48291(14) 0.85549(9) 0.0259(4) Uani 1 1 d . .
H7 H -0.3708 0.4868 0.8846 0.031 Uiso 1 1 calc R U
C8 C -0.0946(4) 0.40597(13) 0.85862(8) 0.0244(4) Uani 1 1 d . .
H8 H -0.1083 0.3575 0.8901 0.029 Uiso 1 1 calc R U
C9 C 0.0839(3) 0.39966(12) 0.81475(8) 0.0203(3) Uani 1 1 d . .
C10 C 0.6334(3) 0.36609(12) 0.68393(8) 0.0205(3) Uani 1 1 d . .
H10 H 0.7719 0.3508 0.7097 0.025 Uiso 1 1 calc R U
N2 N 0.5870(3) 0.27776(10) 0.64653(7) 0.0199(3) Uani 1 1 d . .
C11 C 0.7935(3) 0.23553(14) 0.61860(9) 0.0246(4) Uani 1 1 d . .
H11A H 0.8973 0.2073 0.6502 0.030 Uiso 1 1 calc R U
H11B H 0.8787 0.2855 0.5944 0.030 Uiso 1 1 calc R U
C12 C 0.6949(4) 0.15524(14) 0.57715(10) 0.0296(4) Uani 1 1 d . .
H12A H 0.6775 0.0924 0.5999 0.035 Uiso 1 1 calc R U
H12B H 0.7953 0.1441 0.5409 0.035 Uiso 1 1 calc R U
C13 C 0.4584(4) 0.19620(14) 0.55741(9) 0.0301(4) Uani 1 1 d . .
H13A H 0.4562 0.2105 0.5127 0.036 Uiso 1 1 calc R U
H13B H 0.3342 0.1485 0.5669 0.036 Uiso 1 1 calc R U
C14 C 0.4283(3) 0.29129(13) 0.59494(9) 0.0259(4) Uani 1 1 d . .
H14A H 0.4703 0.3501 0.5703 0.031 Uiso 1 1 calc R U
H14B H 0.2675 0.2985 0.6096 0.031 Uiso 1 1 calc R U
C15 C 0.6926(3) 0.45398(13) 0.64644(8) 0.0220(4) Uani 1 1 d . .
C16 C 0.7528(3) 0.51937(13) 0.61331(8) 0.0220(4) Uani 1 1 d . .
C17 C 0.8403(3) 0.59906(13) 0.57249(8) 0.0234(4) Uani 1 1 d . .
O O 0.9743(3) 0.66762(10) 0.60746(6) 0.0267(3) Uani 1 1 d . .
H1O H 0.876(6) 0.699(2) 0.6284(14) 0.048(8) Uiso 1 1 d . .
C18 C 1.0072(4) 0.55354(15) 0.52601(9) 0.0322(5) Uani 1 1 d . .
H18A H 1.0653 0.6051 0.4984 0.048 Uiso 1 1 calc R U
H18B H 0.9268 0.5031 0.5018 0.048 Uiso 1 1 calc R U
H18C H 1.1367 0.5232 0.5480 0.048 Uiso 1 1 calc R U
C19 C 0.6415(4) 0.65118(15) 0.54012(10) 0.0321(4) Uani 1 1 d . .
H19A H 0.7020 0.7050 0.5146 0.048 Uiso 1 1 calc R U
H19B H 0.5354 0.6781 0.5710 0.048 Uiso 1 1 calc R U
H19C H 0.5592 0.6039 0.5139 0.048 Uiso 1 1 calc R U
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'
O O 0.0492 0.0322 '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
C1 N1 C9 117.85(15)
N1 C1 C2 126.05(16)
N1 C1 Cl 114.83(13)
C2 C1 Cl 119.10(14)
C3 C2 C1 115.95(16)
C3 C2 C10 124.09(15)
C1 C2 C10 119.96(16)
C2 C3 C4 120.76(16)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C9 117.87(16)
C3 C4 C5 123.51(16)
C9 C4 C5 118.62(17)
C6 C5 C4 120.46(17)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 120.37(18)
C5 C6 H6 119.8
C7 C6 H6 119.8
C8 C7 C6 120.81(19)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 119.39(17)
C7 C8 H8 120.3
C9 C8 H8 120.3
N1 C9 C8 118.15(15)
N1 C9 C4 121.50(16)
C8 C9 C4 120.34(17)
N2 C10 C15 113.14(14)
N2 C10 C2 109.43(14)
C15 C10 C2 113.78(15)
N2 C10 H10 106.7
C15 C10 H10 106.7
C2 C10 H10 106.7
C11 N2 C14 104.37(14)
C11 N2 C10 113.46(14)
C14 N2 C10 115.85(13)
N2 C11 C12 102.56(15)
N2 C11 H11A 111.3
C12 C11 H11A 111.3
N2 C11 H11B 111.3
C12 C11 H11B 111.3
H11A C11 H11B 109.2
C11 C12 C13 103.96(15)
C11 C12 H12A 111.0
C13 C12 H12A 111.0
C11 C12 H12B 111.0
C13 C12 H12B 111.0
H12A C12 H12B 109.0
C14 C13 C12 104.85(16)
C14 C13 H13A 110.8
C12 C13 H13A 110.8
C14 C13 H13B 110.8
C12 C13 H13B 110.8
H13A C13 H13B 108.9
N2 C14 C13 103.27(15)
N2 C14 H14A 111.1
C13 C14 H14A 111.1
N2 C14 H14B 111.1
C13 C14 H14B 111.1
H14A C14 H14B 109.1
C16 C15 C10 174.2(2)
C15 C16 C17 177.0(2)
O C17 C16 109.96(15)
O C17 C19 110.81(15)
C16 C17 C19 110.64(16)
O C17 C18 105.56(16)
C16 C17 C18 108.48(15)
C19 C17 C18 111.25(17)
C17 O H1O 104(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.295(2)
N1 C9 1.379(2)
C1 C2 1.431(2)
C1 Cl 1.7422(18)
C2 C3 1.374(3)
C2 C10 1.514(2)
C3 C4 1.416(3)
C3 H3 0.9500
C4 C9 1.418(2)
C4 C5 1.421(2)
C5 C6 1.365(3)
C5 H5 0.9500
C6 C7 1.416(3)
C6 H6 0.9500
C7 C8 1.375(3)
C7 H7 0.9500
C8 C9 1.409(3)
C8 H8 0.9500
C10 N2 1.471(2)
C10 C15 1.482(2)
C10 H10 1.0000
N2 C11 1.459(2)
N2 C14 1.461(2)
C11 C12 1.523(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.541(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.534(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.193(3)
C16 C17 1.486(2)
C17 O 1.429(2)
C17 C19 1.524(3)
C17 C18 1.528(3)
O H1O 0.84(3)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O H1O N1 0.84(3) 2.12(3) 2.896(2) 153(3) 4_656
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
C9 N1 C1 C2 -1.4(3)
C9 N1 C1 Cl 176.86(13)
N1 C1 C2 C3 1.1(3)
Cl C1 C2 C3 -177.06(13)
N1 C1 C2 C10 -179.43(16)
Cl C1 C2 C10 2.4(2)
C1 C2 C3 C4 0.5(2)
C10 C2 C3 C4 -178.97(15)
C2 C3 C4 C9 -1.6(2)
C2 C3 C4 C5 179.45(17)
C3 C4 C5 C6 178.53(17)
C9 C4 C5 C6 -0.4(3)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 1.2(3)
C6 C7 C8 C9 -1.0(3)
C1 N1 C9 C8 179.80(17)
C1 N1 C9 C4 0.1(3)
C7 C8 C9 N1 -179.69(17)
C7 C8 C9 C4 0.0(3)
C3 C4 C9 N1 1.4(2)
C5 C4 C9 N1 -179.65(16)
C3 C4 C9 C8 -178.36(17)
C5 C4 C9 C8 0.6(3)
C3 C2 C10 N2 -111.28(18)
C1 C2 C10 N2 69.3(2)
C3 C2 C10 C15 16.4(2)
C1 C2 C10 C15 -163.07(16)
C15 C10 N2 C11 72.08(19)
C2 C10 N2 C11 -159.92(14)
C15 C10 N2 C14 -48.6(2)
C2 C10 N2 C14 79.36(18)
C14 N2 C11 C12 -46.28(17)
C10 N2 C11 C12 -173.29(14)
N2 C11 C12 C13 31.34(18)
C11 C12 C13 C14 -6.26(19)
C11 N2 C14 C13 42.02(18)
C10 N2 C14 C13 167.53(15)
C12 C13 C14 N2 -20.99(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328250
