#------------------------------------------------------------------------------
#$Date: 2019-11-26 05:20:29 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/80/7238048.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_7238048
loop_
_publ_author_name
'Huang, Yunping'
'Liu, Yun'
'Sommerville, Parker J. W.'
'Kaminsky, Werner'
'Ginger, David S.'
'Luscombe, Christine K.'
_publ_section_title
;
 Theobromine and direct arylation: a sustainable and scalable solution to
 minimize aggregation caused quenching
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/C9GC03391B
_journal_year                    2019
_chemical_formula_moiety         'C46 H54 N8 O4'
_chemical_formula_sum            'C46 H54 N8 O4'
_chemical_formula_weight         782.97
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-06-29T14:19:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-11-01 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                77.216(14)
_cell_angle_beta                 86.717(15)
_cell_angle_gamma                85.596(18)
_cell_formula_units_Z            1
_cell_length_a                   4.7211(18)
_cell_length_b                   13.737(5)
_cell_length_c                   15.384(6)
_cell_measurement_reflns_used    709
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.72
_cell_measurement_wavelength     0.71073
_cell_volume                     969.3(6)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      -0.121358
_diffrn_orient_matrix_UB_12      0.045552
_diffrn_orient_matrix_UB_13      -0.045124
_diffrn_orient_matrix_UB_21      -0.122351
_diffrn_orient_matrix_UB_22      0.020182
_diffrn_orient_matrix_UB_23      0.049133
_diffrn_orient_matrix_UB_31      0.124544
_diffrn_orient_matrix_UB_32      0.055803
_diffrn_orient_matrix_UB_33      -0.00042
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.3039
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4805
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25.155
_diffrn_reflns_theta_min         1.523
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.2578
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.14
_refine_ls_wR_factor_ref         0.1999
_reflns_Friedel_coverage         0
_reflns_number_gt                1196
_reflns_number_total             3404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc03391b2.cif
_cod_data_source_block           shelx
_cod_database_code               7238048
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.999
loop_
_symmetry_equiv_pos_as_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
C1 C 0.1842(12) 0.6687(4) 0.8214(4) 0.0253(15) Uani 1 1 d . U
H1 H 0.1004 0.7136 0.7721 0.03 Uiso 1 1 calc R U
C2 C 0.1218(12) 0.5687(4) 0.8409(4) 0.0279(15) Uani 1 1 d . U
H2 H -0.0091 0.5465 0.8061 0.033 Uiso 1 1 calc R U
C3 C 0.2491(11) 0.5011(4) 0.9108(4) 0.0214(14) Uani 1 1 d . U
C4 C 0.4364(11) 0.5347(3) 0.9641(4) 0.0201(14) Uani 1 1 d . U
C5 C 0.1963(12) 0.3958(4) 0.9286(4) 0.0292(16) Uani 1 1 d . U
H5 H 0.0738 0.3719 0.8922 0.035 Uiso 1 1 calc R U
C6 C 0.3219(12) 0.3322(4) 0.9970(4) 0.0250(15) Uani 1 1 d . U
H6 H 0.2839 0.2635 1.008 0.03 Uiso 1 1 calc R U
C7 C 0.5084(11) 0.3626(4) 1.0535(4) 0.0218(14) Uani 1 1 d . U
C8 C 0.6328(11) 0.2968(3) 1.1269(4) 0.0223(14) Uani 1 1 d . U
C9 C 0.5449(12) 0.1925(4) 1.1560(4) 0.0266(15) Uani 1 1 d . U
C10 C 0.3330(11) 0.0667(3) 1.2242(4) 0.0207(14) Uani 1 1 d . U
C11 C 0.5056(11) 0.0334(3) 1.1616(4) 0.0216(14) Uani 1 1 d . U
C12 C 0.8493(12) 0.1186(4) 1.0416(4) 0.0306(16) Uani 1 1 d . U
H12A H 1.0337 0.0888 1.0638 0.046 Uiso 1 1 calc R U
H12B H 0.8689 0.1883 1.0104 0.046 Uiso 1 1 calc R U
H12C H 0.7837 0.0809 1.0003 0.046 Uiso 1 1 calc R U
C13 C 0.5155(12) -0.0677(4) 1.1506(4) 0.0248(15) Uani 1 1 d . U
C14 C 0.1201(12) -0.0893(4) 1.2678(4) 0.0283(15) Uani 1 1 d . U
C15 C -0.0305(12) 0.0442(4) 1.3469(4) 0.0326(17) Uani 1 1 d . U
H15A H 0.04 0.1066 1.3554 0.049 Uiso 1 1 calc R U
H15B H -0.0245 -0.0058 1.4033 0.049 Uiso 1 1 calc R U
H15C H -0.2268 0.0567 1.3277 0.049 Uiso 1 1 calc R U
C16 C 0.2823(13) -0.2279(3) 1.2016(4) 0.0304(16) Uani 1 1 d . U
H16A H 0.3824 -0.241 1.1466 0.036 Uiso 1 1 calc R U
H16B H 0.0782 -0.2377 1.1979 0.036 Uiso 1 1 calc R U
C17 C 0.4008(12) -0.3018(3) 1.2821(4) 0.0294(16) Uani 1 1 d . U
H17A H 0.3252 -0.2819 1.3374 0.035 Uiso 1 1 calc R U
H17B H 0.6105 -0.3004 1.2801 0.035 Uiso 1 1 calc R U
C18 C 0.3208(12) -0.4075(3) 1.2836(4) 0.0291(16) Uani 1 1 d . U
H18A H 0.4019 -0.4276 1.2289 0.035 Uiso 1 1 calc R U
H18B H 0.1113 -0.4076 1.2828 0.035 Uiso 1 1 calc R U
C19 C 0.4254(13) -0.4846(3) 1.3651(4) 0.0325(16) Uani 1 1 d . U
H19A H 0.6345 -0.4834 1.3665 0.039 Uiso 1 1 calc R U
H19B H 0.3412 -0.4652 1.4197 0.039 Uiso 1 1 calc R U
C20 C 0.3521(13) -0.5893(3) 1.3659(4) 0.0324(16) Uani 1 1 d . U
H20A H 0.4276 -0.6074 1.3098 0.039 Uiso 1 1 calc R U
H20B H 0.1427 -0.5913 1.3676 0.039 Uiso 1 1 calc R U
C21 C 0.4696(13) -0.6670(4) 1.4446(4) 0.0351(17) Uani 1 1 d . U
H21A H 0.6768 -0.6609 1.4459 0.042 Uiso 1 1 calc R U
H21B H 0.3811 -0.6522 1.5005 0.042 Uiso 1 1 calc R U
C22 C 0.4184(13) -0.7739(4) 1.4419(4) 0.0354(17) Uani 1 1 d . U
H22A H 0.2108 -0.7811 1.4445 0.043 Uiso 1 1 calc R U
H22B H 0.4961 -0.7874 1.3843 0.043 Uiso 1 1 calc R U
C23 C 0.5487(13) -0.8505(4) 1.5160(4) 0.0401(18) Uani 1 1 d . U
H23A H 0.5072 -0.9175 1.51 0.06 Uiso 1 1 calc R U
H23B H 0.7551 -0.8453 1.5132 0.06 Uiso 1 1 calc R U
H23C H 0.4694 -0.839 1.5735 0.06 Uiso 1 1 calc R U
N1 N 0.6442(9) 0.1153(3) 1.1160(3) 0.0235(12) Uani 1 1 d . U
N2 N 0.3539(10) 0.1647(3) 1.2218(3) 0.0260(13) Uani 1 1 d . U
N3 N 0.1485(10) 0.0070(3) 1.2788(3) 0.0265(13) Uani 1 1 d . U
N4 N 0.3154(9) -0.1231(3) 1.2070(3) 0.0229(12) Uani 1 1 d . U
O1 O -0.0570(8) -0.1424(2) 1.3109(3) 0.0307(11) Uani 1 1 d . .
O2 O 0.6746(8) -0.1047(2) 1.0988(3) 0.0313(11) 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 0 '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 0.006 '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
C8 C1 C2 120.6(5) 2_667 .
C8 C1 H1 119.7 2_667 .
C2 C1 H1 119.7 . .
C3 C2 C1 120.6(5) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
C2 C3 C4 119.7(4) . .
C2 C3 C5 120.9(5) . .
C4 C3 C5 119.4(5) . .
C3 C4 C7 119.8(5) . 2_667
C3 C4 C4 119.3(6) . 2_667
C7 C4 C4 120.9(6) 2_667 2_667
C6 C5 C3 119.5(5) . .
C6 C5 H5 120.3 . .
C3 C5 H5 120.3 . .
C5 C6 C7 123.2(5) . .
C5 C6 H6 118.4 . .
C7 C6 H6 118.4 . .
C8 C7 C4 119.0(5) . 2_667
C8 C7 C6 123.3(5) . .
C4 C7 C6 117.7(5) 2_667 .
C1 C8 C7 120.2(4) 2_667 .
C1 C8 C9 118.9(5) 2_667 .
C7 C8 C9 120.5(5) . .
N2 C9 N1 112.7(4) . .
N2 C9 C8 123.2(5) . .
N1 C9 C8 124.0(5) . .
N2 C10 C11 112.7(4) . .
N2 C10 N3 125.0(5) . .
C11 C10 N3 122.2(4) . .
C10 C11 N1 105.6(4) . .
C10 C11 C13 122.6(5) . .
N1 C11 C13 131.7(5) . .
N1 C12 H12A 109.5 . .
N1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C13 N4 121.8(4) . .
O2 C13 C11 126.5(5) . .
N4 C13 C11 111.6(5) . .
O1 C14 N3 121.9(5) . .
O1 C14 N4 122.2(5) . .
N3 C14 N4 115.9(5) . .
N3 C15 H15A 109.5 . .
N3 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
N3 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
N4 C16 C17 111.7(4) . .
N4 C16 H16A 109.3 . .
C17 C16 H16A 109.3 . .
N4 C16 H16B 109.3 . .
C17 C16 H16B 109.3 . .
H16A C16 H16B 107.9 . .
C16 C17 C18 111.0(5) . .
C16 C17 H17A 109.4 . .
C18 C17 H17A 109.4 . .
C16 C17 H17B 109.4 . .
C18 C17 H17B 109.4 . .
H17A C17 H17B 108 . .
C17 C18 C19 113.3(5) . .
C17 C18 H18A 108.9 . .
C19 C18 H18A 108.9 . .
C17 C18 H18B 108.9 . .
C19 C18 H18B 108.9 . .
H18A C18 H18B 107.7 . .
C20 C19 C18 113.5(5) . .
C20 C19 H19A 108.9 . .
C18 C19 H19A 108.9 . .
C20 C19 H19B 108.9 . .
C18 C19 H19B 108.9 . .
H19A C19 H19B 107.7 . .
C19 C20 C21 113.5(5) . .
C19 C20 H20A 108.9 . .
C21 C20 H20A 108.9 . .
C19 C20 H20B 108.9 . .
C21 C20 H20B 108.9 . .
H20A C20 H20B 107.7 . .
C22 C21 C20 114.0(5) . .
C22 C21 H21A 108.8 . .
C20 C21 H21A 108.8 . .
C22 C21 H21B 108.8 . .
C20 C21 H21B 108.8 . .
H21A C21 H21B 107.7 . .
C23 C22 C21 114.0(5) . .
C23 C22 H22A 108.8 . .
C21 C22 H22A 108.8 . .
C23 C22 H22B 108.8 . .
C21 C22 H22B 108.8 . .
H22A C22 H22B 107.6 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C11 N1 C9 105.2(4) . .
C11 N1 C12 126.9(4) . .
C9 N1 C12 127.9(4) . .
C9 N2 C10 103.8(4) . .
C10 N3 C14 119.9(5) . .
C10 N3 C15 121.0(4) . .
C14 N3 C15 119.0(4) . .
C13 N4 C14 127.2(4) . .
C13 N4 C16 119.5(5) . .
C14 N4 C16 113.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C8 1.384(7) 2_667
C1 C2 1.389(7) .
C1 H1 0.95 .
C2 C3 1.388(7) .
C2 H2 0.95 .
C3 C4 1.407(7) .
C3 C5 1.450(7) .
C4 C7 1.417(6) 2_667
C4 C4 1.419(10) 2_667
C5 C6 1.344(7) .
C5 H5 0.95 .
C6 C7 1.418(7) .
C6 H6 0.95 .
C7 C8 1.408(7) .
C7 C4 1.417(6) 2_667
C8 C1 1.384(7) 2_667
C8 C9 1.487(7) .
C9 N2 1.327(6) .
C9 N1 1.379(6) .
C10 N2 1.348(6) .
C10 C11 1.360(7) .
C10 N3 1.363(6) .
C11 N1 1.377(6) .
C11 C13 1.434(7) .
C12 N1 1.452(6) .
C12 H12A 0.98 .
C12 H12B 0.98 .
C12 H12C 0.98 .
C13 O2 1.228(6) .
C13 N4 1.396(6) .
C14 O1 1.219(6) .
C14 N3 1.388(6) .
C14 N4 1.404(7) .
C15 N3 1.463(6) .
C15 H15A 0.98 .
C15 H15B 0.98 .
C15 H15C 0.98 .
C16 N4 1.480(6) .
C16 C17 1.521(7) .
C16 H16A 0.99 .
C16 H16B 0.99 .
C17 C18 1.523(7) .
C17 H17A 0.99 .
C17 H17B 0.99 .
C18 C19 1.529(7) .
C18 H18A 0.99 .
C18 H18B 0.99 .
C19 C20 1.502(7) .
C19 H19A 0.99 .
C19 H19B 0.99 .
C20 C21 1.525(7) .
C20 H20A 0.99 .
C20 H20B 0.99 .
C21 C22 1.516(7) .
C21 H21A 0.99 .
C21 H21B 0.99 .
C22 C23 1.496(7) .
C22 H22A 0.99 .
C22 H22B 0.99 .
C23 H23A 0.98 .
C23 H23B 0.98 .
C23 H23C 0.98 .
