#------------------------------------------------------------------------------
#$Date: 2021-07-28 00:32:24 +0300 (Wed, 28 Jul 2021) $
#$Revision: 267765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518921.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_4518921
loop_
_publ_author_name
'Song, Yulong'
'Fu, Chunling'
'Ma, Shengming'
_publ_section_title
;
 Copper-Catalyzed Syntheses of Multiple Functionalizatized Allenes via
 Three-Component Reaction of Enynes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10007
_journal_page_last               10013
_journal_paper_doi               10.1021/acscatal.1c02140
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H23 N3 O'
_chemical_formula_sum            'C25 H23 N3 O'
_chemical_formula_weight         381.46
_space_group_crystal_system      orthorhombic
_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     dual
_audit_creation_date             2020-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.436(4)
_cell_length_b                   9.724(3)
_cell_length_c                   22.389(9)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.28
_cell_volume                     2054.3(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing.data_collection       'Bruker Instrument Service vV6.2.10'
_computing.data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25642
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.152
_diffrn_reflns_theta_min         2.283
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1521 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0283
_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)+(0.0338P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0714
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4303
_reflns_number_total             4542
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c02140_si_002.cif
_cod_data_source_block           200721_syl_6_110_0m
_cod_database_code               4518921
_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.
;
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.74874(12) 0.21398(12) 0.22119(5) 0.0344(3) Uani 1 1 d . . . . .
N1 N 0.60164(15) 0.61857(14) 0.38125(6) 0.0289(3) Uani 1 1 d . . . . .
N2 N 0.13229(16) 0.64142(16) 0.46923(7) 0.0381(3) Uani 1 1 d . . . . .
N3 N 0.77830(18) -0.15049(18) 0.27642(7) 0.0434(4) Uani 1 1 d . . . . .
C1 C 0.81445(16) 0.38031(17) 0.29805(7) 0.0276(3) Uani 1 1 d . . . . .
H1 H 0.911987 0.356444 0.296318 0.033 Uiso 1 1 calc R . . . .
C2 C 0.71656(16) 0.31718(16) 0.26128(7) 0.0271(3) Uani 1 1 d . . . . .
C3 C 0.57231(16) 0.35366(18) 0.26256(7) 0.0304(3) Uani 1 1 d . . . . .
H3 H 0.507574 0.307781 0.236886 0.037 Uiso 1 1 calc R . . . .
C4 C 0.52335(16) 0.45474(17) 0.30038(7) 0.0292(3) Uani 1 1 d . . . . .
H4 H 0.426228 0.480457 0.300739 0.035 Uiso 1 1 calc R . . . .
C5 C 0.62105(16) 0.51805(16) 0.33813(6) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.76537(17) 0.48098(16) 0.33811(6) 0.0267(3) Uani 1 1 d . . . . .
C7 C 0.83144(18) 0.56103(18) 0.38416(7) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.928716 0.558801 0.395055 0.039 Uiso 1 1 calc R . . . .
C8 C 0.72975(19) 0.64025(18) 0.40919(7) 0.0328(4) Uani 1 1 d . . . . .
H8 H 0.744548 0.702050 0.441453 0.039 Uiso 1 1 calc R . . . .
C9 C 0.89400(19) 0.1796(2) 0.21321(9) 0.0418(4) Uani 1 1 d . . . . .
H9A H 0.902313 0.106627 0.183239 0.063 Uiso 1 1 calc GR . . . .
H9B H 0.933610 0.147584 0.251200 0.063 Uiso 1 1 calc GR . . . .
H9C H 0.946170 0.261029 0.199688 0.063 Uiso 1 1 calc GR . . . .
C10 C 0.46741(18) 0.67307(16) 0.40019(7) 0.0298(3) Uani 1 1 d . . . . .
H10A H 0.407093 0.689323 0.364706 0.036 Uiso 1 1 calc R . . . .
H10B H 0.482789 0.762606 0.420214 0.036 Uiso 1 1 calc R . . . .
C11 C 0.39047(16) 0.57600(15) 0.44300(6) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.44854(16) 0.46683(16) 0.46729(6) 0.0251(3) Uani 1 1 d . . . . .
C13 C 0.50884(15) 0.35685(15) 0.48916(6) 0.0235(3) Uani 1 1 d . . . . .
C14 C 0.58546(15) 0.36211(15) 0.54738(6) 0.0232(3) Uani 1 1 d . . . . .
C15 C 0.63949(18) 0.48606(16) 0.56887(7) 0.0291(3) Uani 1 1 d . . . . .
H15 H 0.632560 0.566833 0.545179 0.035 Uiso 1 1 calc R . . . .
C16 C 0.70344(19) 0.49218(18) 0.62474(7) 0.0347(4) Uani 1 1 d . . . . .
H16 H 0.739474 0.577206 0.639099 0.042 Uiso 1 1 calc R . . . .
C17 C 0.71495(18) 0.3747(2) 0.65970(7) 0.0342(4) Uani 1 1 d . . . . .
H17 H 0.757651 0.379166 0.698079 0.041 Uiso 1 1 calc R . . . .
C18 C 0.66367(18) 0.25140(18) 0.63809(7) 0.0319(3) Uani 1 1 d . . . . .
H18 H 0.672160 0.170569 0.661649 0.038 Uiso 1 1 calc R . . . .
C19 C 0.59982(17) 0.24420(16) 0.58229(7) 0.0277(3) Uani 1 1 d . . . . .
H19 H 0.565743 0.158502 0.567840 0.033 Uiso 1 1 calc R . . . .
C20 C 0.24643(17) 0.61063(16) 0.45753(6) 0.0274(3) Uani 1 1 d . . . . .
C21 C 0.50044(16) 0.22410(16) 0.45391(7) 0.0270(3) Uani 1 1 d . . . . .
H21A H 0.436635 0.237067 0.419266 0.032 Uiso 1 1 calc R . . . .
H21B H 0.459825 0.150946 0.479463 0.032 Uiso 1 1 calc R . . . .
C22 C 0.64639(16) 0.17936(16) 0.43185(7) 0.0264(3) Uani 1 1 d . . . . .
H22A H 0.695375 0.259433 0.413975 0.032 Uiso 1 1 calc R . . . .
H22B H 0.703459 0.147525 0.466284 0.032 Uiso 1 1 calc R . . . .
C23 C 0.63766(17) 0.06458(17) 0.38577(7) 0.0289(3) Uani 1 1 d . . . . .
H23A H 0.586040 0.097952 0.350110 0.035 Uiso 1 1 calc R . . . .
H23B H 0.584081 -0.013812 0.402689 0.035 Uiso 1 1 calc R . . . .
C24 C 0.78506(17) 0.01653(18) 0.36748(7) 0.0321(3) Uani 1 1 d . . . . .
H24A H 0.843316 0.097705 0.357019 0.039 Uiso 1 1 calc R . . . .
H24B H 0.830545 -0.029739 0.401891 0.039 Uiso 1 1 calc R . . . .
C25 C 0.78258(17) -0.07809(18) 0.31667(7) 0.0316(3) Uani 1 1 d . . . . .
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 O1 C9 117.68(13) . . ?
C5 N1 C10 125.60(13) . . ?
C8 N1 C5 107.95(13) . . ?
C8 N1 C10 125.67(14) . . ?
C2 C1 H1 121.0 . . ?
C2 C1 C6 117.99(15) . . ?
C6 C1 H1 121.0 . . ?
O1 C2 C1 124.31(14) . . ?
O1 C2 C3 114.17(14) . . ?
C1 C2 C3 121.52(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.13(14) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.78(14) . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 130.27(15) . . ?
N1 C5 C6 107.97(13) . . ?
C4 C5 C6 121.74(14) . . ?
C1 C6 C5 119.78(14) . . ?
C1 C6 C7 133.88(15) . . ?
C5 C6 C7 106.33(14) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 C6 107.37(15) . . ?
C8 C7 H7 126.3 . . ?
N1 C8 H8 124.8 . . ?
C7 C8 N1 110.33(14) . . ?
C7 C8 H8 124.8 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
N1 C10 C11 112.09(13) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C12 C11 C10 124.12(15) . . ?
C12 C11 C20 119.36(14) . . ?
C20 C11 C10 116.51(13) . . ?
C13 C12 C11 177.46(15) . . ?
C12 C13 C14 120.71(14) . . ?
C12 C13 C21 118.64(13) . . ?
C14 C13 C21 120.65(13) . . ?
C15 C14 C13 120.56(13) . . ?
C19 C14 C13 120.59(14) . . ?
C19 C14 C15 118.80(14) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.42(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.39(15) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.30(14) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.74(15) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.33(15) . . ?
C18 C19 H19 119.8 . . ?
N2 C20 C11 178.41(18) . . ?
C13 C21 H21A 109.4 . . ?
C13 C21 H21B 109.4 . . ?
C13 C21 C22 111.36(13) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C21 112.30(13) . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C22 C23 C24 110.96(13) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 C23 112.78(13) . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
N3 C25 C24 178.53(18) . . ?
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 C2 1.3802(19) . ?
O1 C9 1.422(2) . ?
N1 C5 1.386(2) . ?
N1 C8 1.377(2) . ?
N1 C10 1.437(2) . ?
N2 C20 1.148(2) . ?
N3 C25 1.144(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C1 C6 1.406(2) . ?
C2 C3 1.407(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 C6 1.409(2) . ?
C6 C7 1.434(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.352(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.529(2) . ?
C11 C12 1.313(2) . ?
C11 C20 1.438(2) . ?
C12 C13 1.307(2) . ?
C13 C14 1.491(2) . ?
C13 C21 1.515(2) . ?
C14 C15 1.394(2) . ?
C14 C19 1.394(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.526(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.522(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.523(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.463(2) . ?
