#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:01:50 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/44/1554423.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_1554423
loop_
_publ_author_name
'Xu, Xin-Ming'
'Lei, Chuan-Hu'
'Tong, Shuo'
'Zhu, Jieping'
'Wang, Mei-Xiang'
_publ_section_title
;
 Lewis acid catalyst-steered divergent synthesis of functionalized vicinal
 amino alcohols and pyrroles from tertiary enamides
;
_journal_issue                   21
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3138
_journal_paper_doi               10.1039/C8QO00839F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C17 H0.25 N O'
_chemical_formula_weight         234.43
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-08-06 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.22900(10)
_cell_length_b                   13.6065(2)
_cell_length_c                   14.6177(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1238.92(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8892
_diffrn_reflns_theta_full        71.47
_diffrn_reflns_theta_max         71.47
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    0.647
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             469
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.166
_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   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0343
_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)+(0.0405P)²+0.1237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                2253
_reflns_number_total             2376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00839f2.cif
_cod_data_source_block           20180717tongshuo
_cod_database_code               1554423
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
O1 O 0.7555(2) 0.78108(8) 0.29560(8) 0.0559(3) Uani 1 1 d .
N1 N 0.7393(2) 0.62572(8) 0.22528(8) 0.0395(3) Uani 1 1 d .
C5 C 1.0301(2) 0.64274(11) 0.12861(10) 0.0416(3) Uani 1 1 d .
C4 C 0.8517(2) 0.58003(11) 0.15486(10) 0.0408(3) Uani 1 1 d .
C12 C 0.4199(2) 0.58499(11) 0.32820(11) 0.0438(3) Uani 1 1 d .
C6 C 1.0142(2) 0.72825(11) 0.18154(10) 0.0417(3) Uani 1 1 d .
C7 C 0.8254(2) 0.72102(10) 0.24236(10) 0.0413(3) Uani 1 1 d .
C1 C 0.5673(2) 0.56561(11) 0.25221(10) 0.0422(3) Uani 1 1 d .
C2 C 0.5772(3) 0.48444(11) 0.19683(11) 0.0481(4) Uani 1 1 d .
H2 H 0.4820 0.4318 0.1986 0.058 Uiso 1 1 calc R
C11 C 1.1990(3) 0.63094(13) 0.06835(11) 0.0492(4) Uani 1 1 d .
H11 H 1.2114 0.5745 0.0329 0.059 Uiso 1 1 calc R
C10 C 1.3494(3) 0.70572(14) 0.06224(12) 0.0557(4) Uani 1 1 d .
H10 H 1.4643 0.6988 0.0221 0.067 Uiso 1 1 calc R
C17 C 0.2196(3) 0.53921(13) 0.32852(12) 0.0537(4) Uani 1 1 d .
H17 H 0.1806 0.4988 0.2800 0.064 Uiso 1 1 calc R
C8 C 1.1642(3) 0.80255(13) 0.17500(11) 0.0512(4) Uani 1 1 d .
H8 H 1.1523 0.8592 0.2103 0.061 Uiso 1 1 calc R
C13 C 0.4761(3) 0.64307(12) 0.40339(11) 0.0530(4) Uani 1 1 d .
H13 H 0.6104 0.6729 0.4053 0.064 Uiso 1 1 calc R
C3 C 0.7545(3) 0.49277(12) 0.13642(11) 0.0475(4) Uani 1 1 d .
H3 H 0.7963 0.4472 0.0925 0.057 Uiso 1 1 calc R
C16 C 0.0782(3) 0.55335(14) 0.40050(14) 0.0619(5) Uani 1 1 d .
H16 H -0.0551 0.5225 0.3999 0.074 Uiso 1 1 calc R
C9 C 1.3331(3) 0.79038(14) 0.11427(12) 0.0573(4) Uani 1 1 d .
H9 H 1.4362 0.8394 0.1085 0.069 Uiso 1 1 calc R
C15 C 0.1341(3) 0.61291(14) 0.47306(14) 0.0626(5) Uani 1 1 d .
H15 H 0.0375 0.6236 0.5206 0.075 Uiso 1 1 calc R
C14 C 0.3342(3) 0.65657(13) 0.47483(13) 0.0624(5) Uani 1 1 d .
H14 H 0.3737 0.6953 0.5245 0.075 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'
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'
H H 0.0000 0.0000 '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
C4 N1 C1 109.34(12)
C4 N1 C7 110.28(12)
C1 N1 C7 140.17(13)
C11 C5 C6 120.17(15)
C11 C5 C4 133.05(14)
C6 C5 C4 106.74(13)
C3 C4 N1 108.20(14)
C3 C4 C5 143.25(15)
N1 C4 C5 108.54(12)
C17 C12 C13 118.27(15)
C17 C12 C1 118.87(15)
C13 C12 C1 122.75(14)
C8 C6 C5 121.49(14)
C8 C6 C7 129.01(14)
C5 C6 C7 109.46(13)
O1 C7 N1 126.29(14)
O1 C7 C6 128.95(14)
N1 C7 C6 104.76(12)
C2 C1 N1 105.63(13)
C2 C1 C12 128.39(15)
N1 C1 C12 125.86(13)
C1 C2 C3 109.77(14)
C5 C11 C10 118.07(16)
C9 C10 C11 121.75(16)
C16 C17 C12 120.63(18)
C6 C8 C9 118.08(15)
C14 C13 C12 120.65(17)
C4 C3 C2 107.05(14)
C15 C16 C17 120.31(17)
C10 C9 C8 120.44(16)
C16 C15 C14 119.67(17)
C13 C14 C15 120.42(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2097(18)
N1 C4 1.3917(18)
N1 C1 1.4042(19)
N1 C7 1.4252(18)
C5 C11 1.381(2)
C5 C6 1.401(2)
C5 C4 1.452(2)
C4 C3 1.360(2)
C12 C17 1.395(2)
C12 C13 1.398(2)
C12 C1 1.465(2)
C6 C8 1.380(2)
C6 C7 1.478(2)
C1 C2 1.371(2)
C2 C3 1.419(3)
C11 C10 1.386(2)
C10 C9 1.384(3)
C17 C16 1.386(3)
C8 C9 1.387(2)
C13 C14 1.380(2)
C16 C15 1.380(3)
C15 C14 1.381(3)
