#------------------------------------------------------------------------------
#$Date: 2023-12-11 23:40:09 +0200 (Mon, 11 Dec 2023) $
#$Revision: 288219 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556102.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_1556102
loop_
_publ_author_name
'Li, Guigen'
'Xu, Xin'
'Chen, Dianjun'
'Timmons, Cody'
'Carducci, Michael D.'
'Headley, Allan D.'
_publ_section_title
;
 Asymmetric halo aldol reaction (AHA).
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              329
_journal_page_last               331
_journal_paper_doi               10.1021/ol027344+
_journal_volume                  5
_journal_year                    2003
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 I N O4'
_chemical_formula_sum            'C19 H18 I N O4'
_chemical_formula_weight         451.24
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2879(6)
_cell_length_b                   9.8237(6)
_cell_length_c                   19.8438(13)
_cell_measurement_reflns_used    4637
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.31
_cell_volume                     1810.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23227
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        -0.04
_diffrn_standards_interval_time  1080
_diffrn_standards_number         101
_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_T_max  0.7749
_exptl_absorpt_correction_T_min  0.4801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.05 (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.026(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.0000P] where P=(Fo²+2Fc²)/3''
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0545
_reflns_number_gt                4035
_reflns_number_total             4462
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ol027344%2Bsi20021216_104811.cif
_cod_data_source_block           gl02s2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1556102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7629(3) 0.5375(3) 0.41718(13) 0.0323(5) Uani 1 1 d .
H1A H 0.8096 0.6235 0.4186 0.039 Uiso 1 1 calc R
C2 C 0.7946(3) 0.4397(3) 0.46517(13) 0.0413(7) Uani 1 1 d .
H2A H 0.8628 0.4593 0.4995 0.050 Uiso 1 1 calc R
C3 C 0.7281(3) 0.3142(3) 0.46369(15) 0.0447(7) Uani 1 1 d .
H3A H 0.7507 0.2476 0.4967 0.054 Uiso 1 1 calc R
C4 C 0.6287(3) 0.2858(3) 0.41407(15) 0.0448(7) Uani 1 1 d .
H4A H 0.5831 0.1993 0.4130 0.054 Uiso 1 1 calc R
C5 C 0.5948(3) 0.3826(3) 0.36581(12) 0.0345(5) Uani 1 1 d .
H5A H 0.5256 0.3626 0.3320 0.041 Uiso 1 1 calc R
C6 C 0.6626(2) 0.5098(2) 0.36692(11) 0.0263(4) Uani 1 1 d .
C7 C 0.6254(2) 0.6183(3) 0.31584(11) 0.0267(4) Uani 1 1 d .
H7A H 0.6646 0.7082 0.3308 0.032 Uiso 1 1 calc R
C8 C 0.4639(2) 0.6319(3) 0.29990(12) 0.0349(5) Uani 1 1 d .
H8A H 0.4050 0.5901 0.3360 0.042 Uiso 1 1 calc R
H8B H 0.4364 0.7288 0.2953 0.042 Uiso 1 1 calc R
O9 O 0.44442(18) 0.5603(2) 0.23676(9) 0.0390(4) Uani 1 1 d .
C10 C 0.5709(3) 0.5434(2) 0.20479(13) 0.0299(5) Uani 1 1 d .
O11 O 0.57844(19) 0.4971(2) 0.14918(9) 0.0399(4) Uani 1 1 d .
N12 N 0.6799(2) 0.58556(19) 0.24753(9) 0.0248(4) Uani 1 1 d .
C13 C 0.8264(2) 0.6022(2) 0.23467(11) 0.0260(5) Uani 1 1 d .
O14 O 0.90266(17) 0.64087(19) 0.28019(8) 0.0315(4) Uani 1 1 d .
C15 C 0.8874(2) 0.5734(2) 0.16510(11) 0.0254(5) Uani 1 1 d .
H15A H 0.8074 0.5554 0.1326 0.030 Uiso 1 1 calc R
C16 C 0.9745(3) 0.6948(2) 0.14195(13) 0.0321(5) Uani 1 1 d .
H16A H 1.0135 0.6765 0.0964 0.038 Uiso 1 1 calc R
H16B H 1.0569 0.7082 0.1729 0.038 Uiso 1 1 calc R
I17 I 0.847130(18) 0.877378(17) 0.139284(8) 0.03646(6) Uani 1 1 d .
C18 C 0.9837(2) 0.4459(2) 0.17179(12) 0.0269(5) Uani 1 1 d .
H18A H 1.0546 0.4605 0.2090 0.032 Uiso 1 1 calc R
O19 O 0.88798(19) 0.33852(18) 0.19011(10) 0.0374(4) Uani 1 1 d .
H19A H 0.932(4) 0.273(3) 0.1962(17) 0.056 Uiso 1 1 d .
C20 C 1.0640(2) 0.4165(2) 0.10717(12) 0.0248(5) Uani 1 1 d .
C21 C 1.2119(3) 0.4415(2) 0.10269(13) 0.0294(5) Uani 1 1 d .
H21A H 1.2629 0.4745 0.1408 0.035 Uiso 1 1 calc R
C22 C 1.2840(3) 0.4182(3) 0.04291(15) 0.0382(7) Uani 1 1 d .
H22A H 1.3842 0.4368 0.0401 0.046 Uiso 1 1 calc R
C23 C 1.2127(3) 0.3684(3) -0.01247(13) 0.0379(6) Uani 1 1 d .
H23A H 1.2631 0.3517 -0.0533 0.045 Uiso 1 1 calc R
C24 C 1.0660(3) 0.3428(3) -0.00800(13) 0.0370(6) Uani 1 1 d .
H24A H 1.0161 0.3075 -0.0459 0.044 Uiso 1 1 calc R
C25 C 0.9922(3) 0.3681(3) 0.05087(11) 0.0315(5) Uani 1 1 d .
H25A H 0.8914 0.3522 0.0529 0.038 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 0.0033 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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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
C2 C1 C6 120.0(2)
C2 C1 H1A 120.0
C6 C1 H1A 120.0
C3 C2 C1 120.7(3)
C3 C2 H2A 119.7
C1 C2 H2A 119.7
C4 C3 C2 119.7(3)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 120.5(3)
C3 C4 H4A 119.8
C5 C4 H4A 119.8
C4 C5 C6 120.0(2)
C4 C5 H5A 120.0
C6 C5 H5A 120.0
C1 C6 C5 119.1(2)
C1 C6 C7 119.7(2)
C5 C6 C7 121.1(2)
N12 C7 C6 112.48(18)
N12 C7 C8 99.41(17)
C6 C7 C8 114.9(2)
N12 C7 H7A 109.9
C6 C7 H7A 109.9
C8 C7 H7A 109.9
O9 C8 C7 104.94(19)
O9 C8 H8A 110.8
C7 C8 H8A 110.8
O9 C8 H8B 110.8
C7 C8 H8B 110.8
H8A C8 H8B 108.8
C10 O9 C8 111.00(18)
O11 C10 O9 122.2(2)
O11 C10 N12 129.6(2)
O9 C10 N12 108.2(2)
C10 N12 C13 129.5(2)
C10 N12 C7 112.08(18)
C13 N12 C7 118.37(18)
O14 C13 N12 118.1(2)
O14 C13 C15 121.3(2)
N12 C13 C15 120.60(19)
C16 C15 C13 109.2(2)
C16 C15 C18 110.85(18)
C13 C15 C18 106.77(17)
C16 C15 H15A 110.0
C13 C15 H15A 110.0
C18 C15 H15A 110.0
C15 C16 I17 111.77(15)
C15 C16 H16A 109.3
I17 C16 H16A 109.3
C15 C16 H16B 109.3
I17 C16 H16B 109.3
H16A C16 H16B 107.9
O19 C18 C20 112.5(2)
O19 C18 C15 105.13(18)
C20 C18 C15 111.58(18)
O19 C18 H18A 109.2
C20 C18 H18A 109.2
C15 C18 H18A 109.2
C18 O19 H19A 109(3)
C25 C20 C21 118.8(2)
C25 C20 C18 120.8(2)
C21 C20 C18 120.4(2)
C22 C21 C20 120.1(2)
C22 C21 H21A 119.9
C20 C21 H21A 119.9
C23 C22 C21 120.8(2)
C23 C22 H22A 119.6
C21 C22 H22A 119.6
C22 C23 C24 119.1(2)
C22 C23 H23A 120.4
C24 C23 H23A 120.4
C25 C24 C23 120.7(3)
C25 C24 H24A 119.7
C23 C24 H24A 119.7
C24 C25 C20 120.4(2)
C24 C25 H25A 119.8
C20 C25 H25A 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(4)
C1 C6 1.391(3)
C1 H1A 0.9500
C2 C3 1.379(4)
C2 H2A 0.9500
C3 C4 1.378(4)
C3 H3A 0.9500
C4 C5 1.386(4)
C4 H4A 0.9500
C5 C6 1.400(3)
C5 H5A 0.9500
C6 C7 1.511(3)
C7 N12 1.482(3)
C7 C8 1.539(3)
C7 H7A 1.0000
C8 O9 1.448(3)
C8 H8A 0.9900
C8 H8B 0.9900
O9 C10 1.346(3)
C10 O11 1.196(3)
C10 N12 1.384(3)
N12 C13 1.394(3)
C13 O14 1.209(3)
C13 C15 1.519(3)
C15 C16 1.512(3)
C15 C18 1.545(3)
C15 H15A 1.0000
C16 I17 2.150(2)
C16 H16A 0.9900
C16 H16B 0.9900
C18 O19 1.427(3)
C18 C20 1.511(3)
C18 H18A 1.0000
O19 H19A 0.77(3)
C20 C25 1.385(3)
C20 C21 1.398(3)
C21 C22 1.381(4)
C21 H21A 0.9500
C22 C23 1.373(4)
C22 H22A 0.9500
C23 C24 1.388(4)
C23 H23A 0.9500
C24 C25 1.377(3)
C24 H24A 0.9500
C25 H25A 0.9500
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
O19 H19A O14 0.77(3) 2.06(3) 2.810(2) 162(4) 3_745
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
C6 C1 C2 C3 0.2(4)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 -0.2(4)
C3 C4 C5 C6 0.5(4)
C2 C1 C6 C5 0.1(4)
C2 C1 C6 C7 178.3(2)
C4 C5 C6 C1 -0.5(4)
C4 C5 C6 C7 -178.7(2)
C1 C6 C7 N12 110.4(2)
C5 C6 C7 N12 -71.4(3)
C1 C6 C7 C8 -136.8(2)
C5 C6 C7 C8 41.4(3)
N12 C7 C8 O9 19.9(3)
C6 C7 C8 O9 -100.4(2)
C7 C8 O9 C10 -18.1(3)
C8 O9 C10 O11 -173.6(2)
C8 O9 C10 N12 7.5(3)
O11 C10 N12 C13 9.2(4)
O9 C10 N12 C13 -171.9(2)
O11 C10 N12 C7 -171.8(3)
O9 C10 N12 C7 7.0(3)
C6 C7 N12 C10 105.1(2)
C8 C7 N12 C10 -17.0(3)
C6 C7 N12 C13 -75.8(2)
C8 C7 N12 C13 162.1(2)
C10 N12 C13 O14 179.8(2)
C7 N12 C13 O14 1.0(3)
C10 N12 C13 C15 0.4(3)
C7 N12 C13 C15 -178.48(19)
O14 C13 C15 C16 -51.3(3)
N12 C13 C15 C16 128.2(2)
O14 C13 C15 C18 68.7(3)
N12 C13 C15 C18 -111.9(2)
C13 C15 C16 I17 -58.3(2)
C18 C15 C16 I17 -175.71(15)
C16 C15 C18 O19 -176.92(19)
C13 C15 C18 O19 64.2(2)
C16 C15 C18 C20 -54.7(3)
C13 C15 C18 C20 -173.59(19)
O19 C18 C20 C25 46.7(3)
C15 C18 C20 C25 -71.2(3)
O19 C18 C20 C21 -135.1(2)
C15 C18 C20 C21 107.0(2)
C25 C20 C21 C22 0.1(4)
C18 C20 C21 C22 -178.1(2)
C20 C21 C22 C23 -1.0(4)
C21 C22 C23 C24 0.6(4)
C22 C23 C24 C25 0.6(4)
C23 C24 C25 C20 -1.6(4)
C21 C20 C25 C24 1.2(4)
C18 C20 C25 C24 179.4(2)
