#------------------------------------------------------------------------------
#$Date: 2022-01-03 22:59:17 +0200 (Mon, 03 Jan 2022) $
#$Revision: 271740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/92/4519244.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_4519244
loop_
_publ_author_name
'Han, Xiao-Qing'
'Wang, Lei'
'Yang, Ping'
'Liu, Jing-Yuan'
'Xu, Wei-Yan'
'Zheng, Chao'
'Liang, Ren-Xiao'
'You, Shu-Li'
'Zhang, Junliang'
'Jia, Yi-Xia'
_publ_section_title
;
 Enantioselective Dearomative Mizoroki--Heck Reaction of Naphthalenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              655
_journal_page_last               661
_journal_paper_doi               10.1021/acscatal.1c05008
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.40
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-16
_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                120
_cell_formula_units_Z            9
_cell_length_a                   28.6928(9)
_cell_length_b                   28.6928(9)
_cell_length_c                   5.8824(3)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      72.44
_cell_measurement_theta_min      3.08
_cell_volume                     4194.0(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.504
_diffrn_reflns_theta_min         1.778
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1564 before and 0.0669 after correction.
The Ratio of minimum to maximum transmission is 0.7838.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       needle
_exptl_crystal_F_000             1674
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 3247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     737
_refine_ls_number_reflns         10987
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0559
_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)+(0.0804P)²+0.1057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.978
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                9158
_reflns_number_total             10987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c05008_si_005.cif
_cod_data_source_block           cu_210115_hxq_13_50_0m_a_tw
_cod_database_code               4519244
_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   0.963
_shelx_estimated_absorpt_t_min   0.823
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.599(2)
 0.401(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2a), C3(H3), C4(H4), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C33(H33), C34(H34), C38(H38), C39(H39),
 C40(H40), C41(H41), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49),
  C50(H50), C51(H51), C52(H52), C57(H57), C58(H58), C62(H62), C63(H63),
 C64(H64), C65(H65), C67(H67), C68(H68), C69(H69), C70(H70), C71(H71)
3.b Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C48(H48a,H48b,H48c), C72(H72a,H72b,H72c)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4a), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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 0.2033(2) -0.0506(2) 0.7020(7) 0.0485(11) Uani 1 1 d . . . . .
O2 O 0.1074(2) -0.1537(2) 0.6717(8) 0.0558(13) Uani 1 1 d . . . . .
H2 H 0.133431 -0.125121 0.722180 0.084 Uiso 1 1 calc GR . . . .
N1 N 0.2528(2) 0.0277(3) 0.5080(9) 0.0506(14) Uani 1 1 d . . . . .
C1 C 0.2815(4) 0.1038(3) 0.2271(14) 0.062(2) Uani 1 1 d . . . . .
H1 H 0.316519 0.125145 0.289417 0.074 Uiso 1 1 calc R . . . .
C2 C 0.2653(4) 0.1213(4) 0.0416(15) 0.067(2) Uani 1 1 d . . . . .
H2A H 0.289173 0.155266 -0.024677 0.081 Uiso 1 1 calc R . . . .
C3 C 0.2139(4) 0.0897(3) -0.0495(14) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.203007 0.102340 -0.176662 0.072 Uiso 1 1 calc R . . . .
C4 C 0.1786(3) 0.0398(3) 0.0438(11) 0.0484(15) Uani 1 1 d . . . . .
H4 H 0.143792 0.018105 -0.019902 0.058 Uiso 1 1 calc R . . . .
C5 C 0.1945(3) 0.0221(3) 0.2300(10) 0.0409(13) Uani 1 1 d . . . . .
C6 C 0.2461(3) 0.0548(3) 0.3197(11) 0.0451(15) Uani 1 1 d . . . . .
C7 C 0.2084(3) -0.0196(3) 0.5485(9) 0.0412(14) Uani 1 1 d . . . . .
C8 C 0.1658(3) -0.0301(3) 0.3622(9) 0.0379(13) Uani 1 1 d . . . . .
C9 C 0.1599(3) -0.0769(3) 0.2246(10) 0.0434(14) Uani 1 1 d . . . . .
H9 H 0.182958 -0.070772 0.098400 0.052 Uiso 1 1 calc R . . . .
C10 C 0.1230(3) -0.1264(3) 0.2781(11) 0.0483(16) Uani 1 1 d . . . . .
H10 H 0.120531 -0.154763 0.185776 0.058 Uiso 1 1 calc R . . . .
C11 C 0.0847(3) -0.1415(3) 0.4737(10) 0.0435(14) Uani 1 1 d . . . . .
C12 C 0.0759(3) -0.0949(3) 0.5351(10) 0.0412(14) Uani 1 1 d . . . . .
C13 C 0.1136(3) -0.0416(3) 0.4763(9) 0.0384(13) Uani 1 1 d . . . . .
C14 C 0.1041(3) -0.0004(3) 0.5333(11) 0.0456(15) Uani 1 1 d . . . . .
H14 H 0.129533 0.035425 0.490782 0.055 Uiso 1 1 calc R . . . .
C15 C 0.0581(3) -0.0105(4) 0.6521(12) 0.0510(18) Uani 1 1 d . . . . .
H15 H 0.051727 0.018182 0.687440 0.061 Uiso 1 1 calc R . . . .
C16 C 0.0218(3) -0.0621(4) 0.7179(13) 0.057(2) Uani 1 1 d . . . . .
H16 H -0.008925 -0.069004 0.804611 0.068 Uiso 1 1 calc R . . . .
C17 C 0.0300(3) -0.1040(3) 0.6581(11) 0.0484(16) Uani 1 1 d . . . . .
H17 H 0.004187 -0.139721 0.700918 0.058 Uiso 1 1 calc R . . . .
C18 C 0.0331(3) -0.1913(3) 0.4160(12) 0.0525(17) Uani 1 1 d . . . . .
C19 C 0.0110(4) -0.2384(4) 0.5460(15) 0.066(2) Uani 1 1 d . . . . .
H19 H 0.028291 -0.239575 0.681801 0.079 Uiso 1 1 calc R . . . .
C20 C -0.0363(5) -0.2833(4) 0.476(2) 0.081(3) Uani 1 1 d . . . . .
H20 H -0.050710 -0.315327 0.564056 0.097 Uiso 1 1 calc R . . . .
C21 C -0.0631(4) -0.2825(4) 0.2805(19) 0.080(3) Uani 1 1 d . . . . .
H21 H -0.095954 -0.313278 0.237336 0.096 Uiso 1 1 calc R . . . .
C22 C -0.0410(4) -0.2357(4) 0.1479(16) 0.079(3) Uani 1 1 d . . . . .
H22 H -0.058084 -0.234762 0.011049 0.094 Uiso 1 1 calc R . . . .
C23 C 0.0057(4) -0.1913(4) 0.2181(14) 0.067(2) Uani 1 1 d . . . . .
H23 H 0.019913 -0.159294 0.129895 0.080 Uiso 1 1 calc R . . . .
C24 C 0.3017(3) 0.0503(4) 0.6446(15) 0.071(2) Uani 1 1 d . . . . .
H24A H 0.293555 0.056141 0.800299 0.107 Uiso 1 1 calc GR . . . .
H24B H 0.328796 0.084657 0.578877 0.107 Uiso 1 1 calc GR . . . .
H24C H 0.315507 0.025226 0.646471 0.107 Uiso 1 1 calc GR . . . .
O3 O 0.4024(2) 0.2566(2) 0.2989(7) 0.0454(11) Uani 1 1 d . . . . .
O4 O 0.4133(2) 0.1646(2) 0.3388(8) 0.0476(11) Uani 1 1 d . . . . .
H4A H 0.403272 0.187180 0.314945 0.071 Uiso 1 1 calc GR . . . .
N2 N 0.4226(2) 0.3351(2) 0.4823(9) 0.0431(12) Uani 1 1 d . . . . .
C25 C 0.4600(3) 0.4128(3) 0.7556(13) 0.0500(16) Uani 1 1 d . . . . .
H25 H 0.441684 0.429507 0.691357 0.060 Uiso 1 1 calc R . . . .
C26 C 0.4943(4) 0.4347(3) 0.9433(14) 0.0552(18) Uani 1 1 d . . . . .
H26 H 0.500115 0.467698 1.006211 0.066 Uiso 1 1 calc R . . . .
C27 C 0.5202(4) 0.4092(3) 1.0400(13) 0.0511(17) Uani 1 1 d . . . . .
H27 H 0.542802 0.424792 1.168545 0.061 Uiso 1 1 calc R . . . .
C28 C 0.5132(3) 0.3614(3) 0.9501(11) 0.0444(15) Uani 1 1 d . . . . .
H28 H 0.530994 0.344258 1.015524 0.053 Uiso 1 1 calc R . . . .
C29 C 0.4800(3) 0.3393(3) 0.7639(10) 0.0382(13) Uani 1 1 d . . . . .
C30 C 0.4543(3) 0.3655(3) 0.6694(11) 0.0413(14) Uani 1 1 d . . . . .
C31 C 0.4260(2) 0.2906(3) 0.4497(10) 0.0395(14) Uani 1 1 d . . . . .
C32 C 0.4634(2) 0.2880(3) 0.6366(9) 0.0356(13) Uani 1 1 d . . . . .
C33 C 0.4270(3) 0.2386(3) 0.7784(10) 0.0394(14) Uani 1 1 d . . . . .
H33 H 0.407995 0.242042 0.903479 0.047 Uiso 1 1 calc R . . . .
C34 C 0.4215(3) 0.1920(3) 0.7322(11) 0.0431(14) Uani 1 1 d . . . . .
H34 H 0.399028 0.162680 0.828662 0.052 Uiso 1 1 calc R . . . .
C35 C 0.4486(3) 0.1812(3) 0.5330(10) 0.0394(14) Uani 1 1 d . . . . .
C36 C 0.5004(3) 0.2324(3) 0.4710(9) 0.0361(13) Uani 1 1 d . . . . .
C37 C 0.5081(3) 0.2831(3) 0.5253(9) 0.0338(12) Uani 1 1 d . . . . .
C38 C 0.5562(3) 0.3291(3) 0.4646(11) 0.0428(14) Uani 1 1 d . . . . .
H38 H 0.561545 0.363491 0.504305 0.051 Uiso 1 1 calc R . . . .
C39 C 0.5959(3) 0.3256(4) 0.3487(12) 0.0494(18) Uani 1 1 d . . . . .
H39 H 0.628819 0.357216 0.312442 0.059 Uiso 1 1 calc R . . . .
C40 C 0.5871(3) 0.2751(4) 0.2852(12) 0.0486(17) Uani 1 1 d . . . . .
H40 H 0.613390 0.272227 0.197361 0.058 Uiso 1 1 calc R . . . .
C41 C 0.5406(3) 0.2292(3) 0.3491(11) 0.0448(15) Uani 1 1 d . . . . .
H41 H 0.535771 0.194921 0.310047 0.054 Uiso 1 1 calc R . . . .
C42 C 0.4578(3) 0.1352(3) 0.5948(11) 0.0443(15) Uani 1 1 d . . . . .
C43 C 0.4864(4) 0.1388(4) 0.7948(13) 0.063(2) Uani 1 1 d . . . . .
H43 H 0.502137 0.170911 0.882274 0.075 Uiso 1 1 calc R . . . .
C44 C 0.4914(5) 0.0951(4) 0.8643(13) 0.067(2) Uani 1 1 d . . . . .
H44 H 0.509156 0.097160 1.003375 0.080 Uiso 1 1 calc R . . . .
C45 C 0.4713(4) 0.0494(4) 0.7357(16) 0.065(2) Uani 1 1 d . . . . .
H45 H 0.475187 0.020002 0.785368 0.078 Uiso 1 1 calc R . . . .
C46 C 0.4447(3) 0.0459(3) 0.5291(16) 0.060(2) Uani 1 1 d . . . . .
H46 H 0.431097 0.014553 0.437059 0.072 Uiso 1 1 calc R . . . .
C47 C 0.4387(3) 0.0890(3) 0.4628(13) 0.0526(17) Uani 1 1 d . . . . .
H47 H 0.421015 0.086917 0.323455 0.063 Uiso 1 1 calc R . . . .
C48 C 0.3896(3) 0.3496(4) 0.3436(14) 0.057(2) Uani 1 1 d . . . . .
H48A H 0.373517 0.365660 0.440479 0.086 Uiso 1 1 calc GR . . . .
H48B H 0.360942 0.317296 0.269987 0.086 Uiso 1 1 calc GR . . . .
H48C H 0.412061 0.375633 0.227300 0.086 Uiso 1 1 calc GR . . . .
O5 O 0.5220(2) 0.5912(2) 0.7495(8) 0.0473(11) Uani 1 1 d . . . . .
O6 O 0.4196(2) 0.4983(2) 0.7167(9) 0.0501(12) Uani 1 1 d . . . . .
H6 H 0.453130 0.518331 0.727019 0.075 Uiso 1 1 calc GR . . . .
N3 N 0.5784(2) 0.6704(3) 0.5664(11) 0.0494(14) Uani 1 1 d . . . . .
C49 C 0.6160(3) 0.7486(3) 0.2939(16) 0.061(2) Uani 1 1 d . . . . .
H49 H 0.651034 0.766479 0.358934 0.073 Uiso 1 1 calc R . . . .
C50 C 0.6035(4) 0.7703(4) 0.1078(17) 0.065(2) Uani 1 1 d . . . . .
H50 H 0.630147 0.803551 0.044719 0.078 Uiso 1 1 calc R . . . .
C51 C 0.5526(3) 0.7438(3) 0.0146(15) 0.0576(19) Uani 1 1 d . . . . .
H51 H 0.544695 0.759130 -0.112445 0.069 Uiso 1 1 calc R . . . .
C52 C 0.5126(3) 0.6953(3) 0.1024(13) 0.0508(16) Uani 1 1 d . . . . .
H52 H 0.477653 0.677250 0.036718 0.061 Uiso 1 1 calc R . . . .
C53 C 0.5248(3) 0.6738(3) 0.2870(12) 0.0437(14) Uani 1 1 d . . . . .
C54 C 0.5763(3) 0.7006(3) 0.3805(12) 0.0457(15) Uani 1 1 d . . . . .
C55 C 0.5311(3) 0.6253(3) 0.5993(11) 0.0410(14) Uani 1 1 d . . . . .
C56 C 0.4906(2) 0.6216(3) 0.4161(10) 0.0380(13) Uani 1 1 d . . . . .
C57 C 0.4775(3) 0.5730(3) 0.2698(11) 0.0406(13) Uani 1 1 d . . . . .
H57 H 0.498587 0.577257 0.138481 0.049 Uiso 1 1 calc R . . . .
C58 C 0.4368(3) 0.5244(3) 0.3235(11) 0.0425(14) Uani 1 1 d . . . . .
H58 H 0.430712 0.494591 0.231750 0.051 Uiso 1 1 calc R . . . .
C59 C 0.3999(3) 0.5145(3) 0.5231(11) 0.0421(14) Uani 1 1 d . . . . .
C60 C 0.3980(3) 0.5647(3) 0.5843(11) 0.0389(13) Uani 1 1 d . . . . .
C61 C 0.4410(3) 0.6161(3) 0.5290(11) 0.0384(13) Uani 1 1 d . . . . .
C62 C 0.4379(3) 0.6611(3) 0.5885(13) 0.0486(16) Uani 1 1 d . . . . .
H62 H 0.466066 0.695855 0.546482 0.058 Uiso 1 1 calc R . . . .
C63 C 0.3940(4) 0.6557(4) 0.7092(14) 0.057(2) Uani 1 1 d . . . . .
H63 H 0.392525 0.687052 0.749412 0.068 Uiso 1 1 calc R . . . .
C64 C 0.3524(3) 0.6060(4) 0.7718(13) 0.0549(19) Uani 1 1 d . . . . .
H64 H 0.322780 0.602743 0.857112 0.066 Uiso 1 1 calc R . . . .
C65 C 0.3547(3) 0.5611(3) 0.7079(12) 0.0469(15) Uani 1 1 d . . . . .
H65 H 0.326026 0.526558 0.749076 0.056 Uiso 1 1 calc R . . . .
C66 C 0.3446(3) 0.4675(3) 0.4595(12) 0.0496(16) Uani 1 1 d . . . . .
C67 C 0.3203(4) 0.4210(3) 0.5882(15) 0.0570(19) Uani 1 1 d . . . . .
H67 H 0.335808 0.418742 0.727504 0.068 Uiso 1 1 calc R . . . .
C68 C 0.2724(4) 0.3774(4) 0.509(2) 0.073(3) Uani 1 1 d . . . . .
H68 H 0.255451 0.344842 0.593881 0.088 Uiso 1 1 calc R . . . .
C69 C 0.2493(4) 0.3813(4) 0.3070(17) 0.074(3) Uani 1 1 d . . . . .
H69 H 0.217164 0.351146 0.252916 0.089 Uiso 1 1 calc R . . . .
C70 C 0.2727(4) 0.4288(4) 0.1846(16) 0.082(3) Uani 1 1 d . . . . .
H70 H 0.256230 0.432067 0.050125 0.098 Uiso 1 1 calc R . . . .
C71 C 0.3203(4) 0.4712(4) 0.2615(14) 0.066(2) Uani 1 1 d . . . . .
H71 H 0.337024 0.503796 0.177289 0.079 Uiso 1 1 calc R . . . .
C72 C 0.6259(3) 0.6860(5) 0.7077(17) 0.070(2) Uani 1 1 d . . . . .
H72A H 0.615577 0.662827 0.842346 0.104 Uiso 1 1 calc GR . . . .
H72B H 0.641099 0.723583 0.755261 0.104 Uiso 1 1 calc GR . . . .
H72C H 0.652769 0.682061 0.620263 0.104 Uiso 1 1 calc GR . . . .
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
C11 O2 H2 109.5 . . ?
C6 N1 C24 123.4(7) . . ?
C7 N1 C6 111.9(5) . . ?
C7 N1 C24 124.6(6) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.5(8) . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.5(8) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(7) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(7) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.1(6) . . ?
C4 C5 C8 131.0(6) . . ?
C6 C5 C8 109.8(5) . . ?
C1 C6 N1 129.6(7) . . ?
C1 C6 C5 122.1(6) . . ?
C5 C6 N1 108.3(6) . . ?
O1 C7 N1 125.1(6) . . ?
O1 C7 C8 125.7(6) . . ?
N1 C7 C8 109.1(5) . . ?
C5 C8 C7 100.7(5) . . ?
C5 C8 C13 115.6(5) . . ?
C9 C8 C5 111.7(5) . . ?
C9 C8 C7 106.1(5) . . ?
C9 C8 C13 112.7(6) . . ?
C13 C8 C7 108.9(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 117.5 . . ?
C9 C10 C11 124.9(6) . . ?
C11 C10 H10 117.5 . . ?
O2 C11 C10 109.3(6) . . ?
O2 C11 C12 108.1(5) . . ?
O2 C11 C18 107.3(6) . . ?
C10 C11 C12 110.4(5) . . ?
C18 C11 C10 109.5(6) . . ?
C18 C11 C12 112.0(6) . . ?
C13 C12 C11 121.5(6) . . ?
C13 C12 C17 117.9(6) . . ?
C17 C12 C11 120.6(6) . . ?
C12 C13 C8 118.9(6) . . ?
C14 C13 C8 121.0(6) . . ?
C14 C13 C12 119.9(6) . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(8) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(7) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(7) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.3(7) . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C11 123.7(7) . . ?
C19 C18 C23 118.0(8) . . ?
C23 C18 C11 118.3(7) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(9) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(9) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.2(9) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.1(10) . . ?
C23 C22 H22 120.4 . . ?
C18 C23 H23 118.8 . . ?
C22 C23 C18 122.3(9) . . ?
C22 C23 H23 118.8 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C35 O4 H4A 109.5 . . ?
C30 N2 C48 124.6(6) . . ?
C31 N2 C30 111.5(5) . . ?
C31 N2 C48 123.9(6) . . ?
C26 C25 H25 121.8 . . ?
C30 C25 H25 121.8 . . ?
C30 C25 C26 116.3(7) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.5(7) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(7) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.6 . . ?
C29 C28 C27 118.8(7) . . ?
C29 C28 H28 120.6 . . ?
C28 C29 C30 119.6(6) . . ?
C28 C29 C32 130.9(6) . . ?
C30 C29 C32 109.5(5) . . ?
C25 C30 N2 128.0(6) . . ?
C25 C30 C29 123.0(6) . . ?
C29 C30 N2 109.0(6) . . ?
O3 C31 N2 125.5(6) . . ?
O3 C31 C32 125.6(6) . . ?
N2 C31 C32 108.9(6) . . ?
C29 C32 C31 101.1(5) . . ?
C29 C32 C33 111.9(5) . . ?
C29 C32 C37 116.1(5) . . ?
C33 C32 C31 105.2(5) . . ?
C37 C32 C31 109.7(5) . . ?
C37 C32 C33 111.7(5) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 C32 121.3(6) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 H34 117.9 . . ?
C33 C34 C35 124.1(6) . . ?
C35 C34 H34 117.9 . . ?
O4 C35 C34 109.2(5) . . ?
O4 C35 C36 108.3(5) . . ?
O4 C35 C42 107.7(5) . . ?
C36 C35 C34 109.8(5) . . ?
C42 C35 C34 108.9(5) . . ?
C42 C35 C36 112.8(6) . . ?
C37 C36 C35 121.5(6) . . ?
C37 C36 C41 118.6(6) . . ?
C41 C36 C35 119.8(6) . . ?
C36 C37 C32 119.8(6) . . ?
C36 C37 C38 119.6(6) . . ?
C38 C37 C32 120.5(6) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 C37 121.5(7) . . ?
C39 C38 H38 119.2 . . ?
C38 C39 H39 120.5 . . ?
C38 C39 C40 118.9(7) . . ?
C40 C39 H39 120.5 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.4(7) . . ?
C41 C40 H40 119.8 . . ?
C36 C41 H41 119.6 . . ?
C40 C41 C36 120.9(7) . . ?
C40 C41 H41 119.6 . . ?
C43 C42 C35 119.0(6) . . ?
C47 C42 C35 122.6(6) . . ?
C47 C42 C43 118.4(7) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 C42 119.8(8) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.4 . . ?
C45 C44 C43 121.2(9) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 H45 120.1 . . ?
C44 C45 C46 119.9(8) . . ?
C46 C45 H45 120.1 . . ?
C45 C46 H46 120.6 . . ?
C47 C46 C45 118.8(8) . . ?
C47 C46 H46 120.6 . . ?
C42 C47 H47 119.1 . . ?
C46 C47 C42 121.8(8) . . ?
C46 C47 H47 119.1 . . ?
N2 C48 H48A 109.5 . . ?
N2 C48 H48B 109.5 . . ?
N2 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C59 O6 H6 109.5 . . ?
C54 N3 C72 124.8(7) . . ?
C55 N3 C54 111.8(6) . . ?
C55 N3 C72 123.4(7) . . ?
C50 C49 H49 121.0 . . ?
C54 C49 H49 121.0 . . ?
C54 C49 C50 118.0(7) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 C49 120.3(7) . . ?
C51 C50 H50 119.8 . . ?
C50 C51 H51 119.3 . . ?
C50 C51 C52 121.5(8) . . ?
C52 C51 H51 119.3 . . ?
C51 C52 H52 120.8 . . ?
C53 C52 C51 118.3(7) . . ?
C53 C52 H52 120.8 . . ?
C52 C53 C54 120.1(7) . . ?
C52 C53 C56 130.7(7) . . ?
C54 C53 C56 109.2(6) . . ?
C49 C54 N3 129.2(7) . . ?
C49 C54 C53 121.8(7) . . ?
C53 C54 N3 109.0(6) . . ?
O5 C55 N3 125.1(6) . . ?
O5 C55 C56 125.8(6) . . ?
N3 C55 C56 109.1(5) . . ?
C53 C56 C55 100.9(5) . . ?
C57 C56 C53 111.3(5) . . ?
C57 C56 C55 106.8(5) . . ?
C61 C56 C53 115.7(6) . . ?
C61 C56 C55 109.7(5) . . ?
C61 C56 C57 111.5(5) . . ?
C56 C57 H57 119.6 . . ?
C58 C57 C56 120.8(6) . . ?
C58 C57 H57 119.6 . . ?
C57 C58 H58 118.5 . . ?
C57 C58 C59 123.1(6) . . ?
C59 C58 H58 118.5 . . ?
O6 C59 C58 108.8(6) . . ?
O6 C59 C60 109.0(5) . . ?
O6 C59 C66 108.0(5) . . ?
C58 C59 C60 111.2(5) . . ?
C58 C59 C66 107.2(6) . . ?
C60 C59 C66 112.5(6) . . ?
C61 C60 C59 120.7(6) . . ?
C65 C60 C59 120.5(6) . . ?
C65 C60 C61 118.8(6) . . ?
C60 C61 C56 120.1(6) . . ?
C62 C61 C56 120.8(6) . . ?
C62 C61 C60 119.0(6) . . ?
C61 C62 H62 119.8 . . ?
C61 C62 C63 120.4(7) . . ?
C63 C62 H62 119.8 . . ?
C62 C63 H63 119.3 . . ?
C64 C63 C62 121.4(8) . . ?
C64 C63 H63 119.3 . . ?
C63 C64 H64 120.8 . . ?
C65 C64 C63 118.4(7) . . ?
C65 C64 H64 120.8 . . ?
C60 C65 H65 119.0 . . ?
C64 C65 C60 122.0(7) . . ?
C64 C65 H65 119.0 . . ?
C67 C66 C59 121.3(7) . . ?
C67 C66 C71 120.2(8) . . ?
C71 C66 C59 118.5(6) . . ?
C66 C67 H67 120.7 . . ?
C66 C67 C68 118.6(9) . . ?
C68 C67 H67 120.7 . . ?
C67 C68 H68 119.8 . . ?
C69 C68 C67 120.4(9) . . ?
C69 C68 H68 119.8 . . ?
C68 C69 H69 119.7 . . ?
C70 C69 C68 120.5(9) . . ?
C70 C69 H69 119.7 . . ?
C69 C70 H70 120.7 . . ?
C71 C70 C69 118.6(10) . . ?
C71 C70 H70 120.7 . . ?
C66 C71 H71 119.2 . . ?
C70 C71 C66 121.6(9) . . ?
C70 C71 H71 119.2 . . ?
N3 C72 H72A 109.5 . . ?
N3 C72 H72B 109.5 . . ?
N3 C72 H72C 109.5 . . ?
H72A C72 H72B 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 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 C7 1.222(8) . ?
O2 H2 0.8400 . ?
O2 C11 1.460(8) . ?
N1 C6 1.421(8) . ?
N1 C7 1.340(10) . ?
N1 C24 1.457(9) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(12) . ?
C1 C6 1.369(11) . ?
C2 H2A 0.9500 . ?
C2 C3 1.395(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(9) . ?
C5 C6 1.401(10) . ?
C5 C8 1.514(9) . ?
C7 C8 1.555(8) . ?
C8 C9 1.505(9) . ?
C8 C13 1.520(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.317(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.498(9) . ?
C11 C12 1.522(10) . ?
C11 C18 1.495(11) . ?
C12 C13 1.405(10) . ?
C12 C17 1.408(9) . ?
C13 C14 1.379(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.373(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(11) . ?
C18 C23 1.407(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.400(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.371(14) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O3 C31 1.239(8) . ?
O4 H4A 0.8400 . ?
O4 C35 1.442(7) . ?
N2 C30 1.417(9) . ?
N2 C31 1.342(9) . ?
N2 C48 1.459(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.402(12) . ?
C25 C30 1.378(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.397(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(10) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(9) . ?
C29 C30 1.405(9) . ?
C29 C32 1.501(9) . ?
C31 C32 1.565(8) . ?
C32 C33 1.522(9) . ?
C32 C37 1.509(9) . ?
C33 H33 0.9500 . ?
C33 C34 1.294(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.522(9) . ?
C35 C36 1.521(9) . ?
C35 C42 1.515(10) . ?
C36 C37 1.394(9) . ?
C36 C41 1.401(9) . ?
C37 C38 1.396(10) . ?
C38 H38 0.9500 . ?
C38 C39 1.372(11) . ?
C39 H39 0.9500 . ?
C39 C40 1.394(13) . ?
C40 H40 0.9500 . ?
C40 C41 1.378(11) . ?
C41 H41 0.9500 . ?
C42 C43 1.407(11) . ?
C42 C47 1.390(10) . ?
C43 H43 0.9500 . ?
C43 C44 1.392(12) . ?
C44 H44 0.9500 . ?
C44 C45 1.368(14) . ?
C45 H45 0.9500 . ?
C45 C46 1.412(14) . ?
C46 H46 0.9500 . ?
C46 C47 1.387(12) . ?
C47 H47 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
O5 C55 1.243(8) . ?
O6 H6 0.8400 . ?
O6 C59 1.448(8) . ?
N3 C54 1.415(9) . ?
N3 C55 1.342(9) . ?
N3 C72 1.462(10) . ?
C49 H49 0.9500 . ?
C49 C50 1.393(13) . ?
C49 C54 1.373(11) . ?
C50 H50 0.9500 . ?
C50 C51 1.379(13) . ?
C51 H51 0.9500 . ?
C51 C52 1.388(11) . ?
C52 H52 0.9500 . ?
C52 C53 1.376(10) . ?
C53 C54 1.394(10) . ?
C53 C56 1.521(9) . ?
C55 C56 1.548(8) . ?
C56 C57 1.517(9) . ?
C56 C61 1.505(9) . ?
C57 H57 0.9500 . ?
C57 C58 1.336(10) . ?
C58 H58 0.9500 . ?
C58 C59 1.509(9) . ?
C59 C60 1.514(10) . ?
C59 C66 1.528(10) . ?
C60 C61 1.408(9) . ?
C60 C65 1.397(9) . ?
C61 C62 1.384(10) . ?
C62 H62 0.9500 . ?
C62 C63 1.388(12) . ?
C63 H63 0.9500 . ?
C63 C64 1.376(13) . ?
C64 H64 0.9500 . ?
C64 C65 1.375(12) . ?
C65 H65 0.9500 . ?
C66 C67 1.381(11) . ?
C66 C71 1.389(12) . ?
C67 H67 0.9500 . ?
C67 C68 1.397(14) . ?
C68 H68 0.9500 . ?
C68 C69 1.394(16) . ?
C69 H69 0.9500 . ?
C69 C70 1.382(15) . ?
C70 H70 0.9500 . ?
C70 C71 1.375(12) . ?
C71 H71 0.9500 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.599(2)
2 0.401(2)
