#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558229.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_1558229
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C17.6 H15.6 N2.4 O2'
_chemical_formula_weight         292.72
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-10T15:53:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.913(4)
_cell_angle_beta                 107.077(3)
_cell_angle_gamma                114.297(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0377(3)
_cell_length_b                   9.8551(4)
_cell_length_c                   10.8773(3)
_cell_measurement_reflns_used    16621
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      76.606
_cell_measurement_theta_min      4.303
_cell_volume                     735.96(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024766
_diffrn_orient_matrix_UB_12      0.0471022
_diffrn_orient_matrix_UB_13      -0.1483886
_diffrn_orient_matrix_UB_21      -0.0734663
_diffrn_orient_matrix_UB_22      0.1684309
_diffrn_orient_matrix_UB_23      0.0099062
_diffrn_orient_matrix_UB_31      0.2010026
_diffrn_orient_matrix_UB_32      -0.004164
_diffrn_orient_matrix_UB_33      -0.0268651
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27457
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.461
_diffrn_reflns_theta_min         4.337
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0038(8)
_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   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     224
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0585P)²+0.0912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0
_reflns_number_gt                2782
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A25_BE75_190
_cod_original_formula_sum        'C17.60 H15.60 N2.40 O2'
_cod_database_code               1558229
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.942
_shelx_shelxl_version_number     2018/3
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16530(11) 0.15816(8) 0.30664(7) 0.0395(2) Uani 1 1 d . . . . .
H1 H 0.198583 0.185663 0.388031 0.059 Uiso 1 1 calc R U . . .
O2 O 0.82471(11) 0.22853(9) 0.43258(7) 0.0450(2) Uani 1 1 d . . . . .
H2A H 0.829114 0.266529 0.505052 0.068 Uiso 1 1 calc R U . . .
N1 N 0.26117(14) 0.24736(11) 0.57116(9) 0.0409(2) Uani 1 1 d . . . . .
N2A N 0.233(4) 0.379(2) 0.939(2) 0.036(3) Uani 0.198(3) 1 d D U P A 1
N3A N 0.260(4) 0.504(2) 0.990(2) 0.039(3) Uani 0.198(3) 1 d D U P A 1
C17 C 0.2141(11) 0.3785(6) 0.9348(5) 0.0334(8) Uani 0.802(3) 1 d D U P A 2
H17 H 0.154412 0.299399 0.97676 0.04 Uiso 0.802(3) 1 calc DR U P A 2
C18 C 0.2683(10) 0.5210(6) 0.9880(6) 0.0318(6) Uani 0.802(3) 1 d D U P A 2
H18 H 0.330993 0.600767 0.947776 0.038 Uiso 0.802(3) 1 calc R U P A 2
N4 N 0.17459(13) 0.65110(10) 1.33258(8) 0.0381(2) Uani 1 1 d . . . . .
C1 C 0.31655(15) 0.15441(10) 0.27779(9) 0.0330(2) Uani 1 1 d . . . . .
C2 C 0.49477(15) 0.19228(10) 0.37451(9) 0.0330(2) Uani 1 1 d . . . . .
H2 H 0.512146 0.220417 0.46389 0.04 Uiso 1 1 calc R U . . .
C3 C 0.64777(15) 0.18925(11) 0.34126(10) 0.0351(2) Uani 1 1 d . . . . .
C4 C 0.62127(17) 0.14519(12) 0.20999(10) 0.0398(3) Uani 1 1 d . . . . .
H4 H 0.724212 0.141294 0.186326 0.048 Uiso 1 1 calc R U . . .
C5 C 0.44260(18) 0.10731(12) 0.11504(10) 0.0409(3) Uani 1 1 d . . . . .
H5 H 0.424534 0.078072 0.025713 0.049 Uiso 1 1 calc R U . . .
C6 C 0.28966(17) 0.11089(11) 0.14670(10) 0.0387(2) Uani 1 1 d . . . . .
H6 H 0.168043 0.084077 0.080079 0.046 Uiso 1 1 calc R U . . .
C7 C 0.32282(16) 0.39392(13) 0.62065(11) 0.0408(3) Uani 1 1 d . . . . .
H7 H 0.372435 0.467016 0.57079 0.049 Uiso 1 1 calc R U . . .
C8 C 0.31858(16) 0.44491(12) 0.73934(10) 0.0383(2) Uani 1 1 d . . . . .
H8 H 0.366109 0.550377 0.770518 0.046 Uiso 1 1 calc R U . . .
C9 C 0.24324(14) 0.33907(11) 0.81322(9) 0.0331(2) Uani 1 1 d D . . . .
C10 C 0.18336(16) 0.18708(12) 0.76358(10) 0.0383(2) Uani 1 1 d . . . . .
H10 H 0.13466 0.111466 0.811703 0.046 Uiso 1 1 calc R U . . .
C11 C 0.19507(16) 0.14676(12) 0.64411(11) 0.0408(3) Uani 1 1 d . . . . .
H11 H 0.154223 0.042553 0.612173 0.049 Uiso 1 1 calc R U . . .
C12 C 0.23361(14) 0.55787(11) 1.10749(9) 0.0325(2) Uani 1 1 d D . . . .
C13 C 0.28742(16) 0.70943(12) 1.15262(10) 0.0382(2) Uani 1 1 d . . . . .
H13 H 0.345426 0.784629 1.106949 0.046 Uiso 1 1 calc R U . . .
C14 C 0.25640(16) 0.75049(12) 1.26395(11) 0.0408(3) Uani 1 1 d . . . . .
H14 H 0.295293 0.854941 1.293305 0.049 Uiso 1 1 calc R U . . .
C15 C 0.12149(15) 0.50441(12) 1.28916(10) 0.0370(2) Uani 1 1 d . . . . .
H15 H 0.062437 0.431855 1.33644 0.044 Uiso 1 1 calc R U . . .
C16 C 0.14832(15) 0.45346(12) 1.17918(10) 0.0362(2) Uani 1 1 d . . . . .
H16 H 0.109129 0.348411 1.152563 0.043 Uiso 1 1 calc DR 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -6 0.0337
5 2 3 0.1012
0 0 7 0.0473
-2 0 6 0.0536
-5 -2 -3 0.1148
0 -1 -7 0.0394
0 -6 -1 0.0564
-5 -5 -1 0.093
1 6 1 0.0529
4 5 1 0.0716
-4 2 0 0.1051
1 -4 3 0.0582
-3 3 -3 0.0956
0 -3 5 0.0488
-3 -4 3 0.0674
0 3 6 0.0455
-1 -4 -6 0.0412
-4 -4 -6 0.0836
-1 -6 -4 0.0452
3 6 4 0.0661
3 6 0 0.0565
0 6 4 0.0506
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 116.96(9) . . ?
N3A N2A C9 126.4(19) . . ?
N2A N3A C12 133.0(19) . . ?
C18 C17 C9 122.2(5) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 121.4(5) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
C14 N4 C15 117.06(9) . . ?
O1 C1 C2 121.93(9) . . ?
O1 C1 C6 118.14(9) . . ?
C2 C1 C6 119.93(10) . . ?
C1 C2 C3 120.42(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.06(9) . . ?
O2 C3 C4 118.10(9) . . ?
C2 C3 C4 119.84(10) . . ?
C5 C4 C3 118.94(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.80(9) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.06(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.97(10) . . ?
N1 C7 H7 118 . . ?
C8 C7 H7 118 . . ?
C7 C8 C9 118.92(10) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 117.23(9) . . ?
C10 C9 N2A 118.7(8) . . ?
C8 C9 N2A 124.0(8) . . ?
C10 C9 C17 118.9(2) . . ?
C8 C9 C17 123.7(2) . . ?
C11 C10 C9 119.70(10) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N1 C11 C10 123.16(10) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C13 C12 C16 116.97(9) . . ?
C13 C12 C18 117.3(2) . . ?
C16 C12 C18 125.7(2) . . ?
C13 C12 N3A 123.5(8) . . ?
C16 C12 N3A 119.5(8) . . ?
C14 C13 C12 119.81(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N4 C14 C13 123.42(10) . . ?
N4 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
N4 C15 C16 123.35(10) . . ?
N4 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 119.39(10) . . ?
C15 C16 H16 120.3 . . ?
C12 C16 H16 120.3 . . ?
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 C1 1.3557(13) . ?
O1 H1 0.84 . ?
O2 C3 1.3555(13) . ?
O2 H2A 0.84 . ?
N1 C11 1.3374(15) . ?
N1 C7 1.3405(14) . ?
N2A N3A 1.228(10) . ?
N2A C9 1.444(16) . ?
N3A C12 1.466(16) . ?
C17 C18 1.327(4) . ?
C17 C9 1.470(5) . ?
C17 H17 0.95 . ?
C18 C12 1.465(4) . ?
C18 H18 0.95 . ?
N4 C14 1.3347(15) . ?
N4 C15 1.3415(14) . ?
C1 C2 1.3903(14) . ?
C1 C6 1.3944(14) . ?
C2 C3 1.3908(15) . ?
C2 H2 0.95 . ?
C3 C4 1.3982(14) . ?
C4 C5 1.3845(17) . ?
C4 H4 0.95 . ?
C5 C6 1.3835(17) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.3764(15) . ?
C7 H7 0.95 . ?
C8 C9 1.3971(15) . ?
C8 H8 0.95 . ?
C9 C10 1.3924(14) . ?
C10 C11 1.3804(15) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.3885(15) . ?
C12 C16 1.3971(14) . ?
C13 C14 1.3795(15) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C16 1.3817(14) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.9 2.7438(11) 177.1 . yes
O2 H2A N4 0.84 1.92 2.7587(11) 177.2 2_667 yes
