#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:45:57 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234283 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/61/4036130.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_4036130
loop_
_publ_author_name
'Yu, Lian'
'Deng, Yuan'
'Cao, Jian'
_publ_section_title
;
 Regioselective Synthesis of Highly Substituted Imidazoles via the
 Sequential Reaction of Allenyl Sulfonamides and Amines.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4729
_journal_page_last               4735
_journal_paper_doi               10.1021/acs.joc.5b00141
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C25 H25 N2 O P'
_chemical_formula_weight         400.44
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 105.763(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.324(2)
_cell_length_b                   8.6176(18)
_cell_length_c                   11.838(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      2.19
_cell_volume                     1111.8(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6167
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0395P)²+0.0912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                3260
_reflns_number_total             3605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00141_si_003.cif
_cod_data_source_block           mo_20141229b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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_original_sg_symbol_H-M      P2(1)
_cod_database_code               4036130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
P1 P 0.28153(4) 0.03514(7) 0.22126(4) 0.03674(14) Uani 1 1 d .
C15 C 0.4910(2) -0.1343(3) 0.2260(2) 0.0507(6) Uani 1 1 d .
H15 H 0.4705 -0.1934 0.2837 0.061 Uiso 1 1 calc R
C11 C 0.11218(19) -0.0584(3) 0.39470(19) 0.0474(6) Uani 1 1 d .
H11A H 0.0864 -0.1133 0.4555 0.057 Uiso 1 1 calc R
H11B H 0.1096 -0.1311 0.3315 0.057 Uiso 1 1 calc R
C17 C 0.6198(2) -0.0893(4) 0.1004(2) 0.0587(7) Uani 1 1 d .
H17 H 0.6873 -0.1169 0.0743 0.070 Uiso 1 1 calc R
C1 C 0.3189(2) -0.0937(3) 0.75706(19) 0.0532(6) Uani 1 1 d .
H1 H 0.3970 -0.1281 0.7578 0.064 Uiso 1 1 calc R
O1 O 0.18201(14) -0.0761(2) 0.16650(12) 0.0467(4) Uani 1 1 d .
C18 C 0.5508(2) 0.0372(4) 0.0531(2) 0.0599(6) Uani 1 1 d .
H18 H 0.5701 0.0936 -0.0064 0.072 Uiso 1 1 calc R
C10 C 0.5534(2) 0.1195(3) 0.4516(2) 0.0555(7) Uani 1 1 d .
H10A H 0.5818 0.2065 0.5023 0.083 Uiso 1 1 calc R
H10B H 0.5459 0.1490 0.3718 0.083 Uiso 1 1 calc R
H10C H 0.6109 0.0356 0.4732 0.083 Uiso 1 1 calc R
C3 C 0.1596(3) -0.0700(4) 0.8540(2) 0.0699(8) Uani 1 1 d .
H3 H 0.1296 -0.0896 0.9183 0.084 Uiso 1 1 calc R
N1 N 0.41506(14) 0.0532(3) 0.57360(13) 0.0430(4) Uani 1 1 d .
C19 C 0.4526(2) 0.0809(3) 0.09411(19) 0.0517(6) Uani 1 1 d .
H19 H 0.4071 0.1683 0.0632 0.062 Uiso 1 1 calc R
C21 C 0.3001(2) 0.3617(3) 0.2366(2) 0.0538(6) Uani 1 1 d .
H21 H 0.3639 0.3472 0.3043 0.065 Uiso 1 1 calc R
N2 N 0.23904(14) -0.0046(2) 0.44298(13) 0.0389(5) Uani 1 1 d .
C6 C 0.24681(19) -0.0200(3) 0.65834(18) 0.0454(6) Uani 1 1 d .
C22 C 0.2665(2) 0.5105(3) 0.1966(2) 0.0653(7) Uani 1 1 d .
H22 H 0.3081 0.5953 0.2374 0.078 Uiso 1 1 calc R
C2 C 0.2759(3) -0.1167(3) 0.8545(2) 0.0656(8) Uani 1 1 d .
H2 H 0.3261 -0.1642 0.9209 0.079 Uiso 1 1 calc R
C7 C 0.29967(18) 0.0102(3) 0.55838(16) 0.0402(5) Uani 1 1 d .
C8 C 0.43089(17) 0.0684(3) 0.46332(17) 0.0392(5) Uani 1 1 d .
C14 C 0.42130(19) -0.0049(2) 0.18125(16) 0.0399(5) Uani 1 1 d .
C20 C 0.23977(18) 0.2345(3) 0.17679(18) 0.0381(5) Uani 1 1 d .
C24 C 0.1116(2) 0.4084(3) 0.0362(2) 0.0534(6) Uani 1 1 d .
H24 H 0.0483 0.4241 -0.0317 0.064 Uiso 1 1 calc R
C25 C 0.14425(19) 0.2586(3) 0.07557(19) 0.0444(5) Uani 1 1 d .
H25 H 0.1024 0.1742 0.0344 0.053 Uiso 1 1 calc R
C5 C 0.1310(2) 0.0307(5) 0.6599(2) 0.0670(7) Uani 1 1 d .
H5 H 0.0815 0.0817 0.5949 0.080 Uiso 1 1 calc R
C16 C 0.5897(2) -0.1768(3) 0.1869(3) 0.0610(7) Uani 1 1 d .
H16 H 0.6360 -0.2635 0.2181 0.073 Uiso 1 1 calc R
C9 C 0.32363(16) 0.0322(3) 0.37928(15) 0.0372(4) Uani 1 1 d .
C13 C -0.1087(2) 0.0127(6) 0.3204(4) 0.1194(16) Uani 1 1 d .
H13A H -0.1220 -0.0622 0.2582 0.179 Uiso 1 1 calc R
H13B H -0.1645 0.0979 0.2963 0.179 Uiso 1 1 calc R
H13C H -0.1225 -0.0350 0.3890 0.179 Uiso 1 1 calc R
C4 C 0.0886(3) 0.0057(5) 0.7577(2) 0.0835(11) Uani 1 1 d .
H4 H 0.0110 0.0407 0.7579 0.100 Uiso 1 1 calc R
C23 C 0.1724(2) 0.5337(4) 0.0972(2) 0.0588(6) Uani 1 1 d .
H23 H 0.1497 0.6339 0.0711 0.071 Uiso 1 1 calc R
C12 C 0.0229(2) 0.0722(4) 0.3485(2) 0.0639(8) Uani 1 1 d .
H12A H 0.0385 0.1152 0.2782 0.077 Uiso 1 1 calc R
H12B H 0.0346 0.1540 0.4068 0.077 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'
P P 0.1023 0.0942 '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
O1 P1 C9 113.52(10)
O1 P1 C14 112.16(10)
C9 P1 C14 105.46(9)
O1 P1 C20 112.05(10)
C9 P1 C20 106.75(11)
C14 P1 C20 106.38(10)
C16 C15 C14 121.1(2)
C16 C15 H15 119.4
C14 C15 H15 119.4
N2 C11 C12 113.1(2)
N2 C11 H11A 109.0
C12 C11 H11A 109.0
N2 C11 H11B 109.0
C12 C11 H11B 109.0
H11A C11 H11B 107.8
C18 C17 C16 120.5(2)
C18 C17 H17 119.8
C16 C17 H17 119.8
C2 C1 C6 120.6(2)
C2 C1 H1 119.7
C6 C1 H1 119.7
C17 C18 C19 119.9(3)
C17 C18 H18 120.1
C19 C18 H18 120.1
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 C3 C2 119.2(2)
C4 C3 H3 120.4
C2 C3 H3 120.4
C7 N1 C8 106.07(15)
C18 C19 C14 120.5(2)
C18 C19 H19 119.8
C14 C19 H19 119.8
C20 C21 C22 120.5(2)
C20 C21 H21 119.7
C22 C21 H21 119.7
C7 N2 C9 106.63(15)
C7 N2 C11 126.48(16)
C9 N2 C11 126.78(16)
C1 C6 C5 118.4(2)
C1 C6 C7 118.64(19)
C5 C6 C7 122.8(2)
C23 C22 C21 120.4(3)
C23 C22 H22 119.8
C21 C22 H22 119.8
C3 C2 C1 120.6(3)
C3 C2 H2 119.7
C1 C2 H2 119.7
N1 C7 N2 111.98(16)
N1 C7 C6 122.48(17)
N2 C7 C6 125.53(18)
N1 C8 C9 110.34(16)
N1 C8 C10 118.71(17)
C9 C8 C10 130.95(18)
C15 C14 C19 118.6(2)
C15 C14 P1 120.16(16)
C19 C14 P1 120.76(17)
C21 C20 C25 118.9(2)
C21 C20 P1 123.15(17)
C25 C20 P1 117.96(17)
C23 C24 C25 120.2(2)
C23 C24 H24 119.9
C25 C24 H24 119.9
C24 C25 C20 120.1(2)
C24 C25 H25 120.0
C20 C25 H25 120.0
C4 C5 C6 120.4(3)
C4 C5 H5 119.8
C6 C5 H5 119.8
C15 C16 C17 119.4(3)
C15 C16 H16 120.3
C17 C16 H16 120.3
C8 C9 N2 104.98(16)
C8 C9 P1 132.71(14)
N2 C9 P1 122.23(13)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C3 C4 C5 120.7(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C22 C23 C24 119.9(3)
C22 C23 H23 120.1
C24 C23 H23 120.1
C11 C12 C13 110.3(3)
C11 C12 H12A 109.6
C13 C12 H12A 109.6
C11 C12 H12B 109.6
C13 C12 H12B 109.6
H12A C12 H12B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4874(16)
P1 C9 1.8008(18)
P1 C14 1.804(2)
P1 C20 1.821(2)
C15 C16 1.371(3)
C15 C14 1.386(3)
C15 H15 0.9300
C11 N2 1.470(3)
C11 C12 1.512(4)
C11 H11A 0.9700
C11 H11B 0.9700
C17 C18 1.370(4)
C17 C16 1.386(4)
C17 H17 0.9300
C1 C2 1.382(3)
C1 C6 1.385(3)
C1 H1 0.9300
C18 C19 1.381(3)
C18 H18 0.9300
C10 C8 1.497(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C3 C4 1.369(4)
C3 C2 1.376(4)
C3 H3 0.9300
N1 C7 1.323(2)
N1 C8 1.371(2)
C19 C14 1.391(3)
C19 H19 0.9300
C21 C20 1.381(3)
C21 C22 1.384(4)
C21 H21 0.9300
N2 C7 1.358(2)
N2 C9 1.407(2)
C6 C5 1.387(3)
C6 C7 1.487(3)
C22 C23 1.371(3)
C22 H22 0.9300
C2 H2 0.9300
C8 C9 1.380(3)
C20 C25 1.395(3)
C24 C23 1.375(4)
C24 C25 1.388(4)
C24 H24 0.9300
C25 H25 0.9300
C5 C4 1.385(3)
C5 H5 0.9300
C16 H16 0.9300
C13 C12 1.525(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C4 H4 0.9300
C23 H23 0.9300
C12 H12A 0.9700
C12 H12B 0.9700
