#------------------------------------------------------------------------------
#$Date: 2016-02-04 23:13:15 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175868 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/82/7118252.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_7118252
loop_
_publ_author_name
'Zhu, Xu'
'Chiba, Shunsuke'
_publ_section_title
;
 Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate
 addition of vinyl azides.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2473
_journal_page_last               2476
_journal_paper_doi               10.1039/c5cc10299e
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C19 H15 N O4'
_chemical_formula_weight         321.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-12-15 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.637(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3566(6)
_cell_length_b                   17.7311(14)
_cell_length_c                   10.5304(7)
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      26.2327
_cell_measurement_theta_min      2.7409
_cell_volume                     1528.24(19)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_unetI/netI     0.1724
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20715
_diffrn_reflns_theta_full        38.64
_diffrn_reflns_theta_max         38.64
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         8575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_gt           0.0822
_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)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2231
_reflns_number_gt                4574
_reflns_number_total             8575
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc10299e2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7118247--7118254.cif.'
_cod_database_code               7118252
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.16826(18) 0.29991(9) 0.57382(14) 0.0127(3) Uani d . . 1
C C2 0.1890(2) 0.23219(10) 0.51201(15) 0.0162(3) Uani d . . 1
H H2 0.2603 0.2304 0.4523 0.019 Uiso calc U R 1
C C3 0.1075(2) 0.16732(10) 0.53612(16) 0.0195(3) Uani d . . 1
H H3 0.124 0.1215 0.4938 0.023 Uiso calc U R 1
C C4 0.0014(2) 0.16936(10) 0.62250(16) 0.0189(3) Uani d . . 1
H H4 -0.056 0.1252 0.638 0.023 Uiso calc U R 1
C C5 -0.0203(2) 0.23593(10) 0.68567(15) 0.0162(3) Uani d . . 1
H H5 -0.0912 0.2376 0.7457 0.019 Uiso calc U R 1
C C6 0.06257(18) 0.29995(9) 0.66018(14) 0.0133(3) Uani d . . 1
C C7 0.12173(18) 0.42865(9) 0.72902(14) 0.0123(3) Uani d . . 1
C C8 0.26524(17) 0.42946(9) 0.65935(13) 0.0105(2) Uani d . . 1
C C9 0.24971(18) 0.37154(9) 0.54779(14) 0.0125(3) Uani d . . 1
H H9 0.3615 0.3595 0.5332 0.015 Uiso calc U R 1
C C10 0.1577(2) 0.41799(10) 0.43111(14) 0.0166(3) Uani d . . 1
H H10A 0.1929 0.4029 0.3505 0.02 Uiso calc U R 1
H H10B 0.0383 0.4101 0.4193 0.02 Uiso calc U R 1
C C11 0.26119(18) 0.50384(9) 0.58274(14) 0.0121(3) Uani d . . 1
C C12 0.31864(17) 0.57755(9) 0.63886(14) 0.0121(3) Uani d . . 1
C C13 0.38068(19) 0.58776(10) 0.77158(14) 0.0142(3) Uani d . . 1
H H13 0.3809 0.5467 0.8296 0.017 Uiso calc U R 1
C C14 0.4417(2) 0.65699(10) 0.81889(16) 0.0178(3) Uani d . . 1
H H14 0.4853 0.663 0.9089 0.021 Uiso calc U R 1
C C15 0.4394(2) 0.71772(11) 0.73552(17) 0.0206(3) Uani d . . 1
H H15 0.4817 0.7652 0.7683 0.025 Uiso calc U R 1
C C16 0.3751(2) 0.70902(10) 0.60415(16) 0.0188(3) Uani d . . 1
H H16 0.3714 0.7508 0.5472 0.023 Uiso calc U R 1
C C17 0.3163(2) 0.63957(10) 0.55595(15) 0.0156(3) Uani d . . 1
H H17 0.274 0.6339 0.4657 0.019 Uiso calc U R 1
C C18 0.41803(18) 0.41563(9) 0.76337(14) 0.0119(3) Uani d . . 1
C C19 0.70288(19) 0.43057(12) 0.81798(17) 0.0211(4) Uani d . . 1
H H19A 0.6943 0.4618 0.8931 0.032 Uiso calc U R 1
H H19B 0.7936 0.4487 0.78 0.032 Uiso calc U R 1
H H19C 0.7228 0.378 0.8455 0.032 Uiso calc U R 1
N N1 0.19902(17) 0.49682(8) 0.46188(12) 0.0159(3) Uani d . . 1
O O1 0.03059(13) 0.36554(7) 0.72428(11) 0.0149(2) Uani d . . 1
O O2 0.08732(14) 0.48160(7) 0.78919(11) 0.0154(2) Uani d . . 1
O O3 0.41521(14) 0.38919(8) 0.86878(11) 0.0184(3) Uani d . . 1
O O4 0.55190(13) 0.43536(7) 0.72221(10) 0.0155(2) Uani d . . 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 117.49(15)
C6 C1 C9 119.56(14)
C2 C1 C9 122.92(14)
C3 C2 C1 121.18(15)
C2 C3 C4 119.94(16)
C5 C4 C3 119.89(16)
C6 C5 C4 119.13(15)
C5 C6 C1 122.38(15)
C5 C6 O1 115.92(13)
C1 C6 O1 121.69(14)
O2 C7 O1 118.37(13)
O2 C7 C8 122.79(15)
O1 C7 C8 118.84(13)
C18 C8 C7 106.16(11)
C18 C8 C11 116.10(13)
C7 C8 C11 108.84(12)
C18 C8 C9 111.63(12)
C7 C8 C9 113.90(12)
C11 C8 C9 100.42(11)
C1 C9 C8 113.41(12)
C1 C9 C10 115.24(13)
C8 C9 C10 101.64(12)
N1 C10 C9 106.00(12)
N1 C11 C12 121.25(14)
N1 C11 C8 113.49(14)
C12 C11 C8 125.25(12)
C13 C12 C17 118.41(15)
C13 C12 C11 122.65(14)
C17 C12 C11 118.91(13)
C14 C13 C12 120.63(15)
C13 C14 C15 120.27(15)
C14 C15 C16 119.85(17)
C17 C16 C15 120.13(16)
C16 C17 C12 120.69(15)
O3 C18 O4 125.19(14)
O3 C18 C8 123.57(13)
O4 C18 C8 111.23(12)
C11 N1 C10 110.12(13)
C7 O1 C6 123.15(12)
C18 O4 C19 115.49(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.390(2)
C1 C2 1.393(2)
C1 C9 1.492(2)
C2 C3 1.386(2)
C3 C4 1.393(2)
C4 C5 1.385(2)
C5 C6 1.384(2)
C6 O1 1.397(2)
C7 O2 1.1995(19)
C7 O1 1.3489(19)
C7 C8 1.527(2)
C8 C18 1.525(2)
C8 C11 1.543(2)
C8 C9 1.546(2)
C9 C10 1.549(2)
C10 N1 1.461(2)
C11 N1 1.2800(19)
C11 C12 1.474(2)
C12 C13 1.401(2)
C12 C17 1.402(2)
C13 C14 1.383(2)
C14 C15 1.387(3)
C15 C16 1.388(2)
C16 C17 1.384(2)
C18 O3 1.2095(18)
C18 O4 1.3257(18)
C19 O4 1.450(2)
