#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:49:19 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572010.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_1572010
loop_
_publ_author_name
'Wang, Xia'
'Wang, Shao-Jie'
'Xin, Xiaolan'
'An, Hao'
'Tu, Zhifeng'
'Yang, Hui'
'Wong, Ming Wah'
'Lu, Shenci'
_publ_section_title
;
 Enantioconvergent and diastereoselective synthesis of atropisomeric
 hydrazides bearing a cyclic quaternary stereocenter through ternary
 catalysis.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              13240
_journal_page_last               13249
_journal_paper_doi               10.1039/d4sc03190c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C36 H42 N4 O11'
_chemical_formula_weight         706.73
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-22 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9652(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.78147(11)
_cell_length_b                   14.09396(13)
_cell_length_c                   16.78114(12)
_cell_measurement_temperature    301(2)
_cell_volume                     3686.92(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            71352
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.415
_diffrn_reflns_theta_min         4.117
_exptl_absorpt_coefficient_mu    0.792
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1496
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         7355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+1.1021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6676
_reflns_number_total             7355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03190c2.cif
_cod_data_source_block           zhailele_0320_auto
_cod_depositor_comments
'Adding full bibliography for 1572009--1572010.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572010
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.40088(8) 0.58682(9) 0.48339(7) 0.0576(3) Uani 1 1 d . . . . .
O2 O 0.06887(15) 0.47270(19) 0.71950(11) 0.1170(7) Uani 1 1 d . . . . .
O3 O 0.01484(14) 0.35989(15) 0.63991(14) 0.1138(7) Uani 1 1 d . . . . .
O4 O 0.17869(8) 0.50306(8) 0.22251(7) 0.0596(3) Uani 1 1 d . . . . .
O5 O 0.25726(7) 0.36849(8) 0.22505(6) 0.0489(3) Uani 1 1 d . . . . .
O6 O 0.28804(8) 0.85886(8) 0.29077(7) 0.0557(3) Uani 1 1 d . . . . .
O7 O 0.35695(8) 0.76665(8) 0.39047(7) 0.0601(3) Uani 1 1 d . . . . .
O8 O 0.01462(11) 0.7384(2) 0.08909(12) 0.1233(8) Uani 1 1 d . . . . .
O9 O 0.13504(11) 0.67729(13) 0.05680(8) 0.0851(5) Uani 1 1 d . . . . .
O10 O 0.42059(8) 0.65366(9) 0.23373(8) 0.0587(3) Uani 1 1 d . . . . .
O11 O 0.42831(7) 0.51732(8) 0.30551(7) 0.0485(3) Uani 1 1 d . . . . .
N1 N 0.26375(8) 0.45594(8) 0.33739(7) 0.0391(3) Uani 1 1 d . . . . .
N2 N 0.06138(12) 0.42871(15) 0.65577(12) 0.0777(5) Uani 1 1 d . . . . .
N3 N 0.31823(7) 0.61428(8) 0.30993(7) 0.0383(3) Uani 1 1 d . . . . .
N4 N 0.27490(8) 0.69853(8) 0.28487(7) 0.0405(3) Uani 1 1 d . . . . .
C1 C 0.28813(9) 0.55185(10) 0.36987(8) 0.0378(3) Uani 1 1 d . . . . .
C2 C 0.36128(10) 0.52700(11) 0.44141(8) 0.0432(3) Uani 1 1 d . . . . .
C3 C 0.36364(11) 0.42528(11) 0.44759(9) 0.0478(4) Uani 1 1 d . . . . .
H3 H 0.398235 0.391162 0.487548 0.057 Uiso 1 1 calc R U . . .
C4 C 0.30845(10) 0.38670(10) 0.38711(8) 0.0421(3) Uani 1 1 d . . . . .
C5 C 0.21369(10) 0.59982(11) 0.40319(9) 0.0450(3) Uani 1 1 d . . . . .
H5A H 0.232340 0.662183 0.423163 0.054 Uiso 1 1 calc R U . . .
H5B H 0.166723 0.608729 0.359136 0.054 Uiso 1 1 calc R U . . .
C6 C 0.18042(10) 0.54651(11) 0.46987(9) 0.0436(3) Uani 1 1 d . . . . .
C7 C 0.20493(12) 0.57407(13) 0.54993(10) 0.0541(4) Uani 1 1 d . . . . .
H7 H 0.247361 0.619886 0.562218 0.065 Uiso 1 1 calc R U . . .
C8 C 0.16762(12) 0.53488(14) 0.61127(11) 0.0597(4) Uani 1 1 d . . . . .
H8 H 0.182844 0.555158 0.664312 0.072 Uiso 1 1 calc R U . . .
C9 C 0.10734(11) 0.46507(13) 0.59175(11) 0.0561(4) Uani 1 1 d . . . . .
C10 C 0.08450(11) 0.43166(13) 0.51439(12) 0.0580(4) Uani 1 1 d . . . . .
H10 H 0.045614 0.382010 0.503437 0.070 Uiso 1 1 calc R U . . .
C11 C 0.12089(10) 0.47387(12) 0.45300(11) 0.0511(4) Uani 1 1 d . . . . .
H11 H 0.105230 0.453286 0.400099 0.061 Uiso 1 1 calc R U . . .
C12 C 0.28809(11) 0.28487(11) 0.37516(9) 0.0471(4) Uani 1 1 d . . . . .
C13 C 0.35417(13) 0.21949(12) 0.37653(11) 0.0595(4) Uani 1 1 d . . . . .
H13 H 0.410970 0.239650 0.385524 0.071 Uiso 1 1 calc R U . . .
C14 C 0.33507(17) 0.12410(14) 0.36442(13) 0.0728(6) Uani 1 1 d . . . . .
H14 H 0.379359 0.080525 0.364644 0.087 Uiso 1 1 calc R U . . .
C15 C 0.25178(17) 0.09323(14) 0.35214(13) 0.0734(6) Uani 1 1 d . . . . .
H15 H 0.239633 0.029200 0.343125 0.088 Uiso 1 1 calc R U . . .
C16 C 0.18613(15) 0.15722(14) 0.35318(13) 0.0700(5) Uani 1 1 d . . . . .
H16 H 0.129594 0.136225 0.346541 0.084 Uiso 1 1 calc R U . . .
C17 C 0.20422(13) 0.25271(12) 0.36409(11) 0.0583(4) Uani 1 1 d . . . . .
H17 H 0.159577 0.295796 0.363986 0.070 Uiso 1 1 calc R U . . .
C18 C 0.22770(9) 0.44537(10) 0.25652(9) 0.0417(3) Uani 1 1 d . . . . .
C19 C 0.23186(13) 0.34397(14) 0.13874(10) 0.0625(5) Uani 1 1 d . . . . .
C20 C 0.2704(2) 0.4188(2) 0.08966(13) 0.0957(8) Uani 1 1 d . . . . .
H20A H 0.240807 0.477870 0.092666 0.143 Uiso 1 1 calc R U . . .
H20B H 0.264755 0.398730 0.034416 0.143 Uiso 1 1 calc R U . . .
H20C H 0.330058 0.426988 0.110948 0.143 Uiso 1 1 calc R U . . .
C21 C 0.2746(2) 0.24876(18) 0.13363(14) 0.0919(8) Uani 1 1 d . . . . .
H21A H 0.335333 0.255184 0.150633 0.138 Uiso 1 1 calc R U . . .
H21B H 0.263979 0.226328 0.078969 0.138 Uiso 1 1 calc R U . . .
H21C H 0.251823 0.204253 0.168049 0.138 Uiso 1 1 calc R U . . .
C22 C 0.13664(17) 0.3358(2) 0.1174(2) 0.1104(10) Uani 1 1 d . . . . .
H22A H 0.114891 0.297112 0.156764 0.166 Uiso 1 1 calc R U . . .
H22B H 0.122461 0.307320 0.065115 0.166 Uiso 1 1 calc R U . . .
H22C H 0.111382 0.397852 0.116781 0.166 Uiso 1 1 calc R U . . .
C23 C 0.30743(9) 0.78230(10) 0.32011(9) 0.0425(3) Uani 1 1 d . . . . .
C24 C 0.39504(15) 0.84683(14) 0.43730(13) 0.0731(6) Uani 1 1 d . . . . .
H24 H 0.370685 0.906637 0.414356 0.088 Uiso 1 1 calc R U . . .
C25 C 0.4884(2) 0.8430(3) 0.4351(2) 0.1382(15) Uani 1 1 d . . . . .
H25A H 0.512092 0.787014 0.462677 0.207 Uiso 1 1 calc R U . . .
H25B H 0.515474 0.898158 0.461235 0.207 Uiso 1 1 calc R U . . .
H25C H 0.498085 0.841204 0.380086 0.207 Uiso 1 1 calc R U . . .
C26 C 0.3761(2) 0.8337(3) 0.52231(18) 0.1187(11) Uani 1 1 d . . . . .
H26A H 0.315182 0.832218 0.521488 0.178 Uiso 1 1 calc R U . . .
H26B H 0.400433 0.885395 0.555453 0.178 Uiso 1 1 calc R U . . .
H26C H 0.400780 0.775028 0.543893 0.178 Uiso 1 1 calc R U . . .
C27 C 0.23276(10) 0.70329(11) 0.20033(9) 0.0442(3) Uani 1 1 d . . . . .
H27A H 0.239098 0.642402 0.174968 0.053 Uiso 1 1 calc R U . . .
H27B H 0.261995 0.750333 0.172322 0.053 Uiso 1 1 calc R U . . .
C28 C 0.13887(10) 0.72793(12) 0.19005(10) 0.0520(4) Uani 1 1 d . . . . .
C29 C 0.09785(14) 0.76047(17) 0.24655(14) 0.0703(5) Uani 1 1 d . . . . .
H29A H 0.0369(16) 0.7789(17) 0.2360(14) 0.083(7) Uiso 1 1 d . . . . .
H29B H 0.1269(16) 0.7724(17) 0.3023(16) 0.083(7) Uiso 1 1 d . . . . .
C30 C 0.08832(13) 0.71576(18) 0.10832(13) 0.0729(6) Uani 1 1 d . . . . .
C31 C 0.0924(3) 0.6625(3) -0.02535(17) 0.1437(16) Uani 1 1 d . . . . .
H31 H 0.058289 0.708719 -0.054088 0.172 Uiso 1 1 calc R U . . .
C32 C 0.1052(4) 0.5805(3) -0.0555(2) 0.186(3) Uani 1 1 d . . . . .
H32A H 0.139750 0.536159 -0.024879 0.223 Uiso 1 1 calc R U . . .
H32B H 0.080008 0.565832 -0.107883 0.223 Uiso 1 1 calc R U . . .
C33 C 0.39364(9) 0.59961(11) 0.27938(9) 0.0421(3) Uani 1 1 d . . . . .
C34 C 0.50807(10) 0.48804(13) 0.27836(10) 0.0505(4) Uani 1 1 d . . . . .
H34 H 0.503694 0.498670 0.220146 0.061 Uiso 1 1 calc R U . . .
C35 C 0.58220(13) 0.54236(19) 0.32177(15) 0.0808(6) Uani 1 1 d . . . . .
H35A H 0.574336 0.608718 0.309986 0.121 Uiso 1 1 calc R U . . .
H35B H 0.634162 0.520938 0.304495 0.121 Uiso 1 1 calc R U . . .
H35C H 0.585882 0.532415 0.378800 0.121 Uiso 1 1 calc R U . . .
C36 C 0.51452(14) 0.38340(15) 0.29589(15) 0.0750(6) Uani 1 1 d . . . . .
H36A H 0.517618 0.373168 0.352824 0.113 Uiso 1 1 calc R U . . .
H36B H 0.565183 0.358473 0.278417 0.113 Uiso 1 1 calc R U . . .
H36C H 0.464888 0.351780 0.267604 0.113 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 0.0181 0.0091 '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 0.0311 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'
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
C18 O5 C19 121.52(12) . . ?
C23 O7 C24 119.23(13) . . ?
C30 O9 C31 116.9(2) . . ?
C33 O11 C34 118.28(12) . . ?
C18 N1 C4 126.59(12) . . ?
C18 N1 C1 119.80(11) . . ?
C4 N1 C1 109.74(11) . . ?
O3 N2 O2 124.4(2) . . ?
O3 N2 C9 117.6(2) . . ?
O2 N2 C9 117.9(2) . . ?
C33 N3 N4 115.04(11) . . ?
C33 N3 C1 123.55(11) . . ?
N4 N3 C1 121.19(11) . . ?
C23 N4 N3 117.63(11) . . ?
C23 N4 C27 117.08(12) . . ?
N3 N4 C27 117.00(11) . . ?
N3 C1 N1 112.73(11) . . ?
N3 C1 C5 109.45(11) . . ?
N1 C1 C5 111.43(12) . . ?
N3 C1 C2 112.29(11) . . ?
N1 C1 C2 101.25(11) . . ?
C5 C1 C2 109.46(11) . . ?
O1 C2 C3 130.43(14) . . ?
O1 C2 C1 122.82(14) . . ?
C3 C2 C1 106.58(13) . . ?
C4 C3 C2 110.02(13) . . ?
C3 C4 N1 112.00(13) . . ?
C3 C4 C12 126.63(14) . . ?
N1 C4 C12 121.14(13) . . ?
C6 C5 C1 115.19(12) . . ?
C11 C6 C7 118.63(14) . . ?
C11 C6 C5 121.24(14) . . ?
C7 C6 C5 119.99(14) . . ?
C8 C7 C6 121.43(17) . . ?
C9 C8 C7 118.02(17) . . ?
C8 C9 C10 122.75(15) . . ?
C8 C9 N2 118.38(18) . . ?
C10 C9 N2 118.76(18) . . ?
C9 C10 C11 118.40(17) . . ?
C6 C11 C10 120.62(16) . . ?
C17 C12 C13 119.00(16) . . ?
C17 C12 C4 121.31(15) . . ?
C13 C12 C4 119.68(16) . . ?
C14 C13 C12 119.7(2) . . ?
C15 C14 C13 120.80(19) . . ?
C14 C15 C16 119.80(19) . . ?
C15 C16 C17 120.0(2) . . ?
C16 C17 C12 120.69(18) . . ?
O4 C18 O5 127.26(14) . . ?
O4 C18 N1 121.58(14) . . ?
O5 C18 N1 111.11(12) . . ?
O5 C19 C22 111.12(18) . . ?
O5 C19 C21 101.97(15) . . ?
C22 C19 C21 111.1(2) . . ?
O5 C19 C20 107.29(17) . . ?
C22 C19 C20 113.3(2) . . ?
C21 C19 C20 111.4(2) . . ?
O6 C23 O7 126.02(14) . . ?
O6 C23 N4 122.40(14) . . ?
O7 C23 N4 111.47(12) . . ?
O7 C24 C25 106.7(2) . . ?
O7 C24 C26 106.79(19) . . ?
C25 C24 C26 111.2(2) . . ?
N4 C27 C28 114.20(12) . . ?
C29 C28 C30 116.96(18) . . ?
C29 C28 C27 125.86(17) . . ?
C30 C28 C27 117.17(16) . . ?
O8 C30 O9 122.9(2) . . ?
O8 C30 C28 125.2(2) . . ?
O9 C30 C28 111.93(17) . . ?
C32 C31 O9 115.0(3) . . ?
O10 C33 O11 126.50(14) . . ?
O10 C33 N3 123.43(14) . . ?
O11 C33 N3 110.03(12) . . ?
O11 C34 C35 110.54(15) . . ?
O11 C34 C36 104.53(13) . . ?
C35 C34 C36 112.59(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 1.2085(19) . ?
O2 N2 1.226(3) . ?
O3 N2 1.221(3) . ?
O4 C18 1.2031(18) . ?
O5 C18 1.3219(18) . ?
O5 C19 1.4823(19) . ?
O6 C23 1.2057(18) . ?
O7 C23 1.3289(19) . ?
O7 C24 1.452(2) . ?
O8 C30 1.201(3) . ?
O9 C30 1.336(3) . ?
O9 C31 1.452(3) . ?
O10 C33 1.2040(18) . ?
O11 C33 1.3273(18) . ?
O11 C34 1.4633(17) . ?
N1 C18 1.3954(18) . ?
N1 C4 1.4009(18) . ?
N1 C1 1.4856(18) . ?
N2 C9 1.478(2) . ?
N3 C33 1.3828(18) . ?
N3 N4 1.4016(16) . ?
N3 C1 1.4699(17) . ?
N4 C23 1.3829(19) . ?
N4 C27 1.4715(18) . ?
C1 C5 1.5343(19) . ?
C1 C2 1.570(2) . ?
C2 C3 1.437(2) . ?
C3 C4 1.345(2) . ?
C4 C12 1.478(2) . ?
C5 C6 1.508(2) . ?
C6 C11 1.389(2) . ?
C6 C7 1.394(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.372(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.389(2) . ?
C12 C17 1.384(3) . ?
C12 C13 1.389(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.369(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.382(3) . ?
C19 C22 1.494(3) . ?
C19 C21 1.511(3) . ?
C19 C20 1.522(3) . ?
C24 C25 1.480(4) . ?
C24 C26 1.514(4) . ?
C27 C28 1.505(2) . ?
C28 C29 1.311(3) . ?
C28 C30 1.485(3) . ?
C31 C32 1.290(5) . ?
C34 C35 1.490(3) . ?
C34 C36 1.504(3) . ?
