#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:36:53 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276674 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158697.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_7158697
loop_
_publ_author_name
'Singh, Prasoon Raj'
'Gopal, Braj'
'Kumar, Madan'
'Goswami, Avijit'
_publ_section_title
;
 A metal-free BF₃·OEt₂ mediated
 chemoselective protocol for the synthesis of propargylic cyclic imines.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4933
_journal_page_last               4941
_journal_paper_doi               10.1039/d2ob00530a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C27 H29 N O4'
_chemical_formula_sum            'C27 H29 N O4'
_chemical_formula_weight         431.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-19 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                75.768(2)
_cell_angle_beta                 71.588(2)
_cell_angle_gamma                87.843(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0386(4)
_cell_length_b                   10.9319(5)
_cell_length_c                   13.2664(6)
_cell_measurement_reflns_used    9197
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.8
_cell_measurement_theta_min      2.4
_cell_volume                     1204.42(10)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'BRUKER APEX-III.PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24228
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      1.2
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_description       'BLOCK TYPE'
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.296
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.156
_exptl_transmission_factor_max   0.7455
_exptl_transmission_factor_min   0.6832
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0568
_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)+(0.0664P)²+0.3631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3621
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00530a2.cif
_cod_data_source_block           shelx
_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/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158697.cif.
;
_cod_database_code               7158697
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60361(19) 0.38587(15) 0.65882(15) 0.0874(5) Uani 1 1 d . . . . .
C1 C 0.4924(3) -0.1455(2) 0.9130(2) 0.0936(8) Uani 1 1 d . . . . .
H1 H 0.570097 -0.100301 0.851817 0.112 Uiso 1 1 calc R U . . .
N1 N 0.13523(18) 0.29729(14) 0.79396(13) 0.0618(4) Uani 1 1 d . . . . .
O2 O 0.60205(16) 0.18905(14) 0.64210(15) 0.0798(5) Uani 1 1 d . . . . .
C2 C 0.5236(3) -0.2610(3) 0.9710(3) 0.1089(10) Uani 1 1 d . . . . .
H2 H 0.622236 -0.293174 0.949097 0.131 Uiso 1 1 calc R U . . .
O3 O 0.4659(2) 0.27812(16) 0.46753(13) 0.0874(5) Uani 1 1 d . . . . .
C3 C 0.4103(3) -0.3281(2) 1.0601(2) 0.0849(7) Uani 1 1 d . . . . .
H3 H 0.431378 -0.406217 1.098999 0.102 Uiso 1 1 calc R U . . .
O4 O 0.2556(2) 0.15803(16) 0.57624(15) 0.0937(5) Uani 1 1 d . . . . .
C4 C 0.2663(3) -0.2810(2) 1.09241(18) 0.0742(6) Uani 1 1 d . . . . .
H4 H 0.189297 -0.327303 1.153430 0.089 Uiso 1 1 calc R U . . .
C6 C 0.3464(2) -0.09591(17) 0.94493(15) 0.0556(4) Uani 1 1 d . . . . .
C5 C 0.2330(2) -0.16520(19) 1.03570(16) 0.0625(5) Uani 1 1 d . . . . .
H5 H 0.134086 -0.133877 1.058631 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2847(2) 0.11786(17) 0.82684(16) 0.0585(5) Uani 1 1 d . . . . .
C7 C 0.3132(2) 0.02181(18) 0.88151(16) 0.0582(5) Uani 1 1 d . . . . .
C9 C 0.2565(2) 0.23597(16) 0.76118(15) 0.0550(4) Uani 1 1 d . . . . .
C10 C 0.3713(2) 0.29768(15) 0.64798(15) 0.0519(4) Uani 1 1 d . . . . .
C11 C 0.5388(2) 0.29843(18) 0.65002(15) 0.0569(5) Uani 1 1 d . . . . .
C12 C 0.7607(3) 0.1744(3) 0.6472(3) 0.1052(9) Uani 1 1 d . . . . .
H12A H 0.817528 0.255525 0.617822 0.126 Uiso 1 1 calc R U . . .
H12B H 0.757997 0.143330 0.722809 0.126 Uiso 1 1 calc R U . . .
C13 C 0.8376(3) 0.0876(4) 0.5852(3) 0.1295(12) Uani 1 1 d . . . . .
H13A H 0.846339 0.121366 0.509446 0.194 Uiso 1 1 calc R U . . .
H13B H 0.778341 0.008644 0.612257 0.194 Uiso 1 1 calc R U . . .
H13C H 0.939912 0.074332 0.592089 0.194 Uiso 1 1 calc R U . . .
C14 C 0.3564(2) 0.23282(18) 0.56213(17) 0.0599(5) Uani 1 1 d . . . . .
C15 C 0.4739(4) 0.2289(3) 0.3732(2) 0.1042(9) Uani 1 1 d . . . . .
H15A H 0.375698 0.185697 0.385336 0.125 Uiso 1 1 calc R U . . .
H15B H 0.493130 0.297798 0.307951 0.125 Uiso 1 1 calc R U . . .
C16 C 0.5977(5) 0.1429(4) 0.3585(3) 0.1352(13) Uani 1 1 d . . . . .
H16A H 0.610539 0.116290 0.292589 0.203 Uiso 1 1 calc R U . . .
H16B H 0.572694 0.070653 0.420043 0.203 Uiso 1 1 calc R U . . .
H16C H 0.692784 0.184166 0.353057 0.203 Uiso 1 1 calc R U . . .
C17 C 0.3075(2) 0.43107(16) 0.62839(16) 0.0595(5) Uani 1 1 d . . . . .
H17A H 0.368755 0.490192 0.644570 0.071 Uiso 1 1 calc R U . . .
H17B H 0.308105 0.461346 0.553111 0.071 Uiso 1 1 calc R U . . .
C18 C 0.1398(2) 0.41407(16) 0.70806(15) 0.0554(4) Uani 1 1 d . . . . .
H18 H 0.071046 0.398778 0.667827 0.067 Uiso 1 1 calc R U . . .
C19 C 0.0829(2) 0.52929(16) 0.75223(15) 0.0514(4) Uani 1 1 d . . . . .
C20 C 0.1323(2) 0.56004(19) 0.83341(16) 0.0609(5) Uani 1 1 d . . . . .
C21 C 0.2411(3) 0.4807(2) 0.8870(2) 0.0858(7) Uani 1 1 d . . . . .
H21A H 0.334089 0.467657 0.831354 0.129 Uiso 1 1 calc R U . . .
H21B H 0.190003 0.400583 0.929355 0.129 Uiso 1 1 calc R U . . .
H21C H 0.268271 0.523725 0.934070 0.129 Uiso 1 1 calc R U . . .
C22 C 0.0823(3) 0.6702(2) 0.86587(18) 0.0689(6) Uani 1 1 d . . . . .
H22 H 0.113543 0.689076 0.920928 0.083 Uiso 1 1 calc R U . . .
C23 C -0.0112(2) 0.75242(19) 0.82031(18) 0.0630(5) Uani 1 1 d . . . . .
C24 C -0.0557(3) 0.8747(2) 0.8546(2) 0.0916(8) Uani 1 1 d . . . . .
H24A H 0.030250 0.935531 0.819421 0.137 Uiso 1 1 calc R U . . .
H24B H -0.081048 0.859209 0.932676 0.137 Uiso 1 1 calc R U . . .
H24C H -0.144671 0.906730 0.833319 0.137 Uiso 1 1 calc R U . . .
C25 C -0.0587(2) 0.72061(18) 0.74101(17) 0.0608(5) Uani 1 1 d . . . . .
H25 H -0.123007 0.774487 0.709568 0.073 Uiso 1 1 calc R U . . .
C26 C -0.0143(2) 0.61057(17) 0.70589(16) 0.0547(4) Uani 1 1 d . . . . .
C27 C -0.0708(3) 0.5851(2) 0.6172(2) 0.0812(7) Uani 1 1 d . . . . .
H27A H -0.122190 0.657513 0.588663 0.122 Uiso 1 1 calc R U . . .
H27B H -0.142688 0.513106 0.647172 0.122 Uiso 1 1 calc R U . . .
H27C H 0.016581 0.568523 0.559236 0.122 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C9 N1 C18 108.92(15) . . ?
C11 O2 C12 117.43(18) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C14 O3 C15 119.5(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C5 C6 C1 118.47(18) . . ?
C5 C6 C7 121.25(18) . . ?
C1 C6 C7 120.22(18) . . ?
C4 C5 C6 120.00(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C8 C9 177.5(2) . . ?
C8 C7 C6 178.1(2) . . ?
N1 C9 C8 121.96(17) . . ?
N1 C9 C10 115.82(15) . . ?
C8 C9 C10 122.21(16) . . ?
C11 C10 C14 111.10(15) . . ?
C11 C10 C9 111.77(15) . . ?
C14 C10 C9 110.63(15) . . ?
C11 C10 C17 112.72(15) . . ?
C14 C10 C17 109.84(15) . . ?
C9 C10 C17 100.33(14) . . ?
O1 C11 O2 124.32(19) . . ?
O1 C11 C10 124.33(18) . . ?
O2 C11 C10 111.35(16) . . ?
C13 C12 O2 109.6(2) . . ?
C13 C12 H12A 109.7 . . ?
O2 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
O2 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
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 . . ?
O4 C14 O3 124.8(2) . . ?
O4 C14 C10 124.9(2) . . ?
O3 C14 C10 110.13(16) . . ?
C16 C15 O3 108.8(3) . . ?
C16 C15 H15A 109.9 . . ?
O3 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
O3 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C10 104.00(14) . . ?
C18 C17 H17A 111.0 . . ?
C10 C17 H17A 111.0 . . ?
C18 C17 H17B 111.0 . . ?
C10 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
N1 C18 C19 114.10(15) . . ?
N1 C18 C17 106.21(14) . . ?
C19 C18 C17 113.82(14) . . ?
N1 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C17 C18 H18 107.5 . . ?
C26 C19 C20 119.10(16) . . ?
C26 C19 C18 118.85(16) . . ?
C20 C19 C18 121.95(16) . . ?
C22 C20 C19 118.95(17) . . ?
C22 C20 C21 117.49(19) . . ?
C19 C20 C21 123.55(18) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 122.96(19) . . ?
C23 C22 H22 118.5 . . ?
C20 C22 H22 118.5 . . ?
C22 C23 C25 117.27(18) . . ?
C22 C23 C24 120.9(2) . . ?
C25 C23 C24 121.83(19) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 C26 122.51(17) . . ?
C23 C25 H25 118.7 . . ?
C26 C25 H25 118.7 . . ?
C25 C26 C19 119.19(17) . . ?
C25 C26 C27 118.45(17) . . ?
C19 C26 C27 122.35(17) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.188(2) . ?
C1 C2 1.378(3) . ?
C1 C6 1.386(3) . ?
C1 H1 0.9300 . ?
N1 C9 1.275(2) . ?
N1 C18 1.480(2) . ?
O2 C11 1.319(2) . ?
O2 C12 1.457(3) . ?
C2 C3 1.360(4) . ?
C2 H2 0.9300 . ?
O3 C14 1.322(2) . ?
O3 C15 1.461(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
O4 C14 1.185(2) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.380(3) . ?
C6 C7 1.432(3) . ?
C5 H5 0.9300 . ?
C8 C7 1.191(3) . ?
C8 C9 1.433(3) . ?
C9 C10 1.536(2) . ?
C10 C11 1.523(3) . ?
C10 C14 1.523(3) . ?
C10 C17 1.540(2) . ?
C12 C13 1.425(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.430(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.536(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.522(2) . ?
C18 H18 0.9800 . ?
C19 C26 1.397(2) . ?
C19 C20 1.402(3) . ?
C20 C22 1.390(3) . ?
C20 C21 1.516(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 C25 1.374(3) . ?
C23 C24 1.516(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.395(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.508(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
